Polymeric fatty acid compounds for treating amino acid-based fibrous substrates, especially hair

Abstract

This invention relates to formula R 1 (–F) x (I) mono-, di-, or polyquaternary ammonium compounds, wherein x is 1–50, and F may be the same or different and is represented by general formula (II), wherein the hydrocarbon group R is optionally substituted and optionally contains a functional group. 1 、R 2 、R 3 、R 4 or R 5 At least one of the compounds contains at least one lactone moiety comprising two or more ester or amide moieties. The invention also relates to processes for synthesizing such compounds, the use of said compounds in cosmetic formulations for skin and hair care, cosmetic compositions for treating fibers, and compositions containing one or more of said compounds for treating hair.

Description

Technical Field

[0001] This invention relates to polymeric fatty acid compounds, their manufacturing processes, compositions containing said compounds, and the use of said compounds in cosmetic compositions including them for skin and hair care, particularly hair care compositions, and their use in treating hair. Background Technology

[0002] Hair can be straight, wavy, curly, coiled, or twisted. Human hair consists of three main morphological components: the cuticle (the outermost thin shell of several concentric layers), the cortex (the main body of the hair), and, in the case of larger diameter hairs, the medulla (the fine central core). The cuticle and cortex provide the mechanical properties of the hair strand, namely its tendency to be wavy, curly, or coiled. Straight hair strands can resemble rods with a circular cross-section, wavy hair strands can appear compressed into an oval cross-section, curly hair strands can appear further compressed into a long, thin elliptical cross-section, and coiled hair strands can have an even flatter cross-section.

[0003] The main component of hair is cross-linked α-helical keratin. Keratin is an intermediate filamentous protein found particularly in epithelial cells such as human skin and hair, wool, feathers, and nails. α-helical type I and II keratin intermediate filaments (KIFs), with a molecular weight of approximately 45-60 kDa, are embedded in the amorphous matrix of keratin-associated proteins (KAPs), with a molecular weight between 20-30 kDa (MA Rogers, L. Langbein, S. Praetzel-Wunder, H. Winter, J. Schweizer, J. Int Rev Cytol. 2006; 251:209-6). Intramolecular and intermolecular disulfide bonds provided by cysteine ​​contribute to the cytoskeletal protein network that maintains the cellular scaffold. In addition to disulfide cross-links, ionic bonds or salt bridges that pair various amino acids found in hair proteins also contribute to the morphology of hair strands.

[0004] It is known in the art that hair can be treated with functionalized silicones and hydrocarbons that provide one or more cosmetic benefits such as conditioning, shine, and UV protection, as well as color retention. Typically, these silicones and hydrocarbon-based derivatives are physically deposited on the fiber surface (cuticle) and are therefore responsible for the appearance of the hair, namely its smoothness, silkiness, friction, evenness, and combability.

[0005] Advanced organosilicon derivatives are generally considered high-performance materials in terms of properties such as smooth and silky hair feel, reduced friction, easy combing, and hair color protection. Corresponding quaternized organosilicones are described in prior art disclosures, namely US 4891166, EP282720, US 2008027202, US 6730766, US 6240929, WO 02 / 10257, WO 02 / 10259, WO 2004 / 069137, WO 2013 / 148629, WO 2013 / 148635, and WO 2013 / 148935.

[0006] Hydrocarbon-based conditioning agents are also widely used. Typically, monoquaternary ammonium compounds are mono-long alkyl–tri-short alkyl quaternary ammonium salts or di-long alkyl–di-short alkyl quaternary ammonium salts, wherein one or both alkyl substituents are selected from aliphatic groups of about 8 to about 30 carbon atoms or aromatic, alkoxy, polyoxyalkylene, alkylamide, hydroxyalkyl, aryl, or alkylaryl groups having up to about 30 carbon atoms; other alkyl groups are independently selected from aliphatic groups of about 1 to about 8 carbon atoms or aromatic, alkoxy, polyoxyalkylene, alkylamide, hydroxyalkyl, aryl, or alkylaryl groups having up to about 8 carbon atoms; and the counterion is a salt-forming anion, for example selected from those of: halogen (e.g., chloride, bromide), acetate, citrate, lactate, glycolate, phosphate, nitrate, sulfonate, sulfate, alkyl sulfate, glutamate, and alkyl sulfonate groups. Alternatively, these monoquaternary ammonium compounds are mono- and di-fatty acid ester quaternary ammonium compounds, as well as fatty acid amide quaternary ammonium compounds, having 10-24 carbon atoms in the alkyl chain. Details of these materials containing quaternary ammonium groups are disclosed, for example, in the following: US 2009 / 0000638, WO 2012 / 027369, US2013 / 259820 and US 5880086, US 6465419, US 6462014, US 6323167, US6037315, US 5854201, US 5750490, US 5463094, and US 2003 / 013627.

[0007] Also known are diquaternized hydrocarbons. Typically, these gemini quaternary ammonium compounds are based on C8-C20 alkyl or aliphatic chains (D. Shukla et al., Cationic Gemini Surfactants: A Review, Journal of Oleo Science 2006, Vol. 55, No. 8, 381-390; MJ Rosen et al., Langmuir (2001), 17, 6148–6154).

[0008] Diquaternized hydrocarbons based on castor oil and alternating copolyesters of different dicarboxylic acids are described in US 2003 / 0007950 and US 6972123.

[0009] Using castor oil precursors to synthesize materials containing three quaternary ammonium groups (EP 0283994, A. Baydar et al., International Journal of Cosmetic Science (1991), 13(4), 169-90).

[0010] Polyquaternary ammonium fatty acid dimer copolymers were synthesized using fatty acid dimers (US 6982078).

[0011] WO 2004 / 093834 describes hydrocarbon-based monoquaternary ammonium compounds for personal care applications. These compounds must contain the structure -CH2CH2O-EO. x -PO y - Linker. Polymerized fatty acids were proposed as hydrophobic tails.

[0012] There is a persistent need for highly effective compounds for treating amino acid-based fibrous matrices, particularly hair: compounds that can be synthesized in a simple, cost-effective, and flexible manner, largely based on sustainable raw materials, are easy to formulate and use, produce long-term stable formulations even in the presence of other performance components, and are useful for hair conditioning, improving dry and wet combability, smoothness, and pleasing neatness. In particular, benefits related to improved wet and dry combability approaching those of silicone-based conditioning agents should be realized.

[0013] The inventors have discovered that novel mono-, di-, and poly(poly)quaternary ammonium compounds based on polymeric fatty acids, namely mono-, di-, and polyquaternary ammonium compounds comprising a lamellar structure, and aqueous compositions comprising such compounds, are suitable for meeting the above requirements. The present invention therefore provides novel mono-, di-, and polyquaternary ammonium lamellar compounds based on polymeric fatty acids, aqueous compositions comprising them, cosmetic compositions comprising them, particularly hair care compositions, and their use in treating hair. These polymeric fatty acid-based mono-, di-, and polyquaternary ammonium lamellar compounds can be synthesized in a simple, cost-effective, and flexible manner, are largely based on sustainable raw materials, are easy to formulate and use, and are useful for hair conditioning, improving dry and wet combability, hair smoothness, and pleasing evenness. Summary of the Invention

[0014] According to the present invention, compounds of the following formula are provided:

[0015] R1 (–F) x (I)

[0016] in

[0017] x is 1-50, preferably 2-50.

[0018] R 1 The hydrocarbon group is selected from those with x valence and optionally substituted, having up to 1000 carbon atoms, preferably 2-300 carbon atoms, more preferably 3-200 carbon atoms, even more preferably 3-150 carbon atoms, particularly 3-50 carbon atoms, and even more particularly 3-20 carbon atoms, and may optionally contain one or more groups selected from: –O-, -NH-, –C(O)–, –C(S)–, tertiary amine groups. And it can be substituted by one or more groups selected from OH groups and halogen groups, and

[0019] F can be the same or different and can be represented by general formula (II).

[0020]

[0021] The group F binds to R. 1 carbon atoms, and

[0022] n is independently 0-100,

[0023] R 2 The hydrocarbon group may be the same as or different from the optionally substituted divalent hydrocarbon group, having up to 1000 carbon atoms, and optionally containing one or more groups selected from: –O–, –NH–, –C(O)–, –C(S)–, tertiary amine group. And it can be substituted by one or more groups selected from OH groups and halogen groups.

[0024] R 3 R 4 R 5 It may be the same as or different from hydrogen and may be selected from linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon groups, having up to 1000 carbon atoms, and optionally containing one or more groups selected from: –O–, –NH–, –C(O)–, –C(S)–, tertiary amine groups. Quaternary ammonium groups And it can be substituted by one or more groups selected from OH groups and halogen groups.

[0025] Where R 3 R 4 R 5 Each is composed of carbon and nitrogen atoms bonded together.

[0026] and preferably R 3 R 4 R 5 It's not hydrogen.

[0027] counterion A of ammonium ions - Selected from monovalent to trivalent inorganic anions and monovalent to 30,000-valent, preferably monovalent to 1,000-valent organic anions, and

[0028] R present in the cation structures of general formulas (I) and (II) 1 R 2 R 3 R 4 R 5 At least one of them contains at least one part having formula (III) or (IV):

[0029] (–X–C(O)–R 6 ) m –X–C(O)– (III), or

[0030] (–C(O)–X–R 6 ) m –C(O)–X– (IV),

[0031] in

[0032] m = 1 - 20,

[0033] X is O or NR 11 ,

[0034] R 11 Independently selected from hydrogen, or optionally substituted, a straight-chain, cyclic, or branched, saturated, unsaturated, or aromatic hydrocarbon group having up to 100 carbon atoms, and optionally containing one or more groups selected from: –O–, –NH–, –C(O)–, –C(S)–, tertiary amine group. And it can be substituted by one or more hydroxyl and halogen groups.

[0035] R 6 Independently selected from optionally substituted straight-chain, cyclic, or branched, saturated or unsaturated hydrocarbon groups having 1-36 carbon atoms.

[0036] The condition is that at least one R 6 Having more than 6 carbon atoms, and

[0037] For x = 1

[0038] R 1 R 3 R 4 R 5Nitrogen atoms that do not bind to the following groups via –OCH2CH2–:

[0039] Detailed Implementation

[0040] According to the present invention, lactones are natural and synthetic compounds, particularly derived from fats and oils, and more particularly from fatty acid compounds that are typically obtainable by hydrolysis of fats and oils.

[0041] The lactone structure is confirmed by a secondary ester bond between a fatty acyl molecule and the alkyl backbone of another fatty acid fragment. The terms "fatty acid" and "fatty acyl molecule" might seem to imply that individual residues need to be derived from fatty components, but this is not the case. The term "fatty acid" as used herein refers to carboxylic acids, particularly unbranched aliphatic monocarboxylic acids, that have chain-like organic radicals. Fatty acids differ from one another in their number of carbon atoms (chain length) and, when unsaturated fatty acids are involved, in the number and position of double bonds. Fatty acids can be classified as short-chain fatty acids with up to 7 carbon atoms, medium-chain fatty acids with 8–12 carbon atoms, long-chain fatty acids with 13–21 carbon atoms, and very long-chain fatty acids with more than 22 carbon atoms.

[0042] According to the present invention, the group "-O-" generally represents an ether group, which also includes an epoxy moiety present as a three-membered ring ether group. Therefore, groups optionally including the group "-O-" as defined above may contain an epoxy group. This is particularly applicable to residues R as defined above that may include terminal epoxy groups. 3 R 4 , and R 5 .

[0043] According to the present invention, residue R 1 The valence is x, where x is 1-50, preferably 2-50, indicating that residue R... 1 It has x residues F as defined by general formula (II). Therefore, the term "x valence" does not involve or limit it to residues R. 1 The number of optional substituents other than F (which may be hydroxyl groups and halogen groups).

[0044] According to the present invention, the term "optionally substituted hydrocarbon group" (which may optionally contain one or more specific groups and may be substituted by one or more specific groups) refers to an organic group that is linked to one or more other groups via at least one of its carbon atoms, wherein the hydrocarbon structure of the group may be interrupted as defined by the specific group contained therein, and one or more hydrogen atoms of the hydrocarbon group may be replaced by substituent groups as indicated.

[0045] In, for example, R 1In this case, one or more hydrogen atoms may be replaced by a hydroxyl group or by a halogen substituent, i.e., by a fluorine, chlorine, bromine or iodine substituent.

[0046] Furthermore, due to the optionally substituted hydrocarbon group R 1 Specifically, it may contain a group selected from –O–, –NH–, –C(O)–, –C(S)– and tertiary amino groups. One or more groups, therefore R 1 The hydrocarbon structure of a group can be interrupted by these groups or combinations thereof. Therefore, the residue may contain ester groups, carboxyl groups, amide groups, ether groups, amino groups, carbonyl groups, thionyl groups, thiocarboxylic acid ester groups, thioester groups, carbamate groups, urethane groups, epoxy groups, and all other groups as detailed for this group, as well as combinations thereof. The same principle applies to optionally substituted hydrocarbon groups R. 2 R 3 R 4 R 5 R 6 , and R 11 .

[0047] R with respect to residue F is x valence 1 The hydrocarbon group structure is preferably selected from linear, branched or cyclic alkyl or alkylene groups, linear, branched or cyclic alkenyl or alkenyl groups, linear, branched or cyclic alkynyl or alkenyl groups, linear, branched or cyclic alkylaryl or alkylenearyl groups, linear, branched or cyclic aralkyl or arylene groups and linear, branched or cyclic aryl or arylene groups such as phenyl or phenylene, benzyl or benzylene, or tolyl or tolyl groups, particularly those having 1 to 30 carbon atoms.

[0048] More preferably, x price R 1The group is selected from alkyl or alkylene groups, which may be selected from linear, branched, and cyclic alkyl or alkylene groups, or groups combining linear and cyclic alkyl or alkylene structures, or groups combining branched and cyclic structures, particularly selected from linear C1-C22 alkyl groups such as methyl and methylene, ethyl and ethylene, n-propyl and n-propylene, n-butyl and n-butylene, n-pentyl and n-pentylene, n-hexyl and n-hexylene, n-heptyl and n-heptylene, or n-octyl and n-octylene. The group comprises branched C1-C22 alkyl and alkylene groups such as isopropyl and isopropylene, isobutyl and isobutylene, tert-butyl and tert-butylene, isopentyl and isobutylene, tert-pentyl and tert-pentylene, neopentyl and neopentylene, and 2-ethylhexyl and 2-ethylhexylene groups, and cyclic C3-C22 alkyl groups such as cyclopropyl or cyclopropylene, cyclobutyl and cyclobutylene, cyclopentyl and cyclopentylene, cyclohexyl and cyclohexylene, and cycloheptyl or cycloheptylene groups.

[0049] When x > 1, regarding which C atom of the hydrocarbon group F bonds to R. 1 There are no restrictions. Regarding R... 1 The presence of functional groups optionally contained in the optional substituents, preferably R 1 Derived from glycidyl compounds, glycerol and glycerol derivatives, especially glycidyl, glycerol, glycerol diglycidyl ether, diglycidyl ether and polyglycerol compounds, or when R 1 When it is a linear alkylene group, especially an alkylene group that does not have any other substituents besides the F group.

[0050] As described above, it is particularly preferred when: R 1 Derived from diglycidyl ether, this means that in the compounds according to the invention, R 2 It is formed as follows: the epoxy ring of the diglycidyl ether is opened by the nitrogen atom, and then a ring with R is formed. 1 The quaternary N atom adjacent to the group. Similarly, it is preferred when: R 1 Derived from diglycidyl ether, monodiglycidyl diglycidyl ether, ditriglycidyl diglycidyl ether, polyglycerols capped with glycidyl units, and poly(epoxyalkane) compounds capped with glycidyl units, particularly poly(ethylene oxide) capped with glycidyl units, poly(propylene oxide) capped with glycidyl units, and poly(butane oxide) capped with glycidyl units.

[0051] It is also preferred when the following is true: R 1This compound is formed by esterifying a polyol, particularly a diol compound such as α,ω-diol or α,ω-dihydroxy polyether, more particularly dihydroxy-terminated poly(ethylene oxide), dihydroxy-terminated poly(propylene oxide), or dihydroxy-terminated poly(butane oxide) with ω-halocarboxylic acids, particularly ω-chloroacetic acid or ω-chloropropionic acid. The latter compound is formed by the following process: R... 1 : The chlorine substituent is replaced by the F group and R 1 The N atom adjacent to the group is substituted.

[0052] Based on this, when R 1 It is preferred when R is a C3-C50 alkylene group containing one or more internal ether or ester groups, and when R 1 Such alkylene groups having hydroxyl substituents are particularly preferred.

[0053] When R 1 When it is a linear C1-C8 alkylene group without other substituents or functional groups, or when R 2 The preferred form is a linear C3-C50 alkylene group derived from diglycidyl ether, glycerol diglycidyl ether, monodiglycidyl diglycidyl ether, monodiethylene glycol diglycidyl ether, or ethylene glycol diglycidyl ether having 3-10 (ethylene oxide) repeating units.

[0054] According to the invention, the term "optionally substituted hydrocarbon residues" does not impose any other restrictions on the groups, and therefore they are limited as follows: the number of carbon atoms of the groups that may be optionally contained or present as substituents, such as the detailed residues, and the manner in which they are bonded to other structural portions of the compounds according to the invention as defined by formula (I), formula (II), formula (III), formula (IV) or any other formula used to define embodiments of the invention.

[0055] For example, in R 2 In this context, the term "divalent" refers to R. 2 Bonded to two quaternary N atoms according to formula (II), but not limited as to R 2 The existence of further substituents as defined.

[0056] Residue R 2 R 3 R 4 R 5 R 6 , and R 11 Therefore, it can be a optionally substituted straight-chain, cyclic, or branched, saturated, unsaturated, or aromatic hydrocarbon group, wherein R 2 and R 6 It is a divalent group, while R 3 R4 R 5 and R 11 It is a monovalent group.

[0057] According to equation (II), R 2 Bonded to two different quaternary N atoms, and R 6 For example, according to the definition of formula (III) or (IV), it is bonded to the carbonyl group of the carboxylic ester or amide moiety on one side and to group X (which may be the O atom of the carboxylic ester group or the NR atom of the amide group) on the other side. 11 (groups), and according to other embodiments of the invention, bonded to other formulas.

[0058] Group R 3 R 4 R 5 and R 11 It is a monovalent group, which may be the same as or different from hydrogen and is selected from, and optionally substituted, straight-chain, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon groups having up to 1000 carbon atoms, and therefore may represent linear i.e., straight-chain, cyclic or branched alkyl groups, linear, cyclic or branched alkenyl groups, linear, cyclic or branched alkynyl groups, linear, cyclic or branched alkylaryl groups, linear, cyclic or branched aralkyl groups and aryl groups, such as phenyl, benzyl or tolyl groups, especially groups having 1-30 carbon atoms, and optionally the aforementioned groups may be substituted by OH or halogen groups, and may optionally contain one or more groups selected from: –O–, –NH–, –C(O)–, –C(S)–, tertiary amino groups. and quaternary ammonium groups

[0059] Preferably, the group R 3 R 4 R 5 and R 11 The group is selected from alkyl groups, which may be linear, branched, and cyclic alkyl groups or groups combining linear and cyclic alkyl units, or structures combining branched and cyclic structures, particularly selected from linear C1-C22 alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-hexyl, n-heptyl, or n-octyl groups; branched C1-C22 alkyl groups such as isopropyl, isobutyl, tert-butyl, isopentyl, tert-pentyl, neopentyl, and 2-ethylhexyl groups; and cyclic C3-C22 alkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl groups, more preferably group R. 3 R 4 R 5 and R 11 It is selected from methyl, ethyl, isopropyl, tert-butyl, cyclopentyl or cyclohexyl groups, with methyl being the most preferred.

[0060] According to the present invention, the group R 2 The hydrocarbon group may be the same as or different from the optionally substituted divalent hydrocarbon group, having up to 1000 carbon atoms, and optionally containing one or more groups selected from: –O–, –NH–, –C(O)–, –C(S)–, tertiary amine group. It can be substituted by one or more groups selected from OH groups and halogen groups, and preferably selected from linear, branched or cyclic alkylene groups, linear, branched or cyclic alkenyl groups, linear, branched or cyclic alkyneyl groups, linear, branched or cyclic alkylene aryl groups, linear, branched or cyclic arylene alkyl groups and linear, branched or cyclic arylene alkyl groups, such as phenylene, benzylene or tolyl groups, especially selected from such groups having 1 to 100 carbon atoms, each optionally containing one or more functional groups as shown above.

[0061] More preferably, R 2 The group is selected from alkylene groups, which may be selected from linear, branched and cyclic alkylene groups or groups combining linear and cyclic alkylene structures, or groups combining branched and cyclic structures, particularly from linear C1-C50 alkylene groups such as methylene, ethylene, n-propylene, n-butylene, n-pentylene, n-hexylene, n-heptylene or n-octylene groups, branched C4-C50 alkylene groups such as isopropylene, isobutylene, tert-butylene, tert-pentylene, neopentylene, 2-ethylhexylene groups, and cyclic C3-C22 alkyl groups such as cyclopropylene, cyclobutylene, cyclopentylene, cyclohexylene and cycloheptylene groups.

[0062] Regarding which C atom of the hydrocarbon group the quaternary N atom bonds to the R... 2 There are no restrictions.

[0063] Regarding R 2 The presence of functional groups optionally contained in the optional substituents, preferably R 2 Derived from glycidyl compounds, glycerol and glycerol derivatives, especially glycidyl, glycerol diglycidyl ether, diglycidyl ether and polyglycerol compounds, or R 2 When it is a linear alkylene group, especially an alkylene group that does not have any substituents other than the quaternary N atom.

[0064] As described above, it is particularly preferred when: R 2 Derived from diglycidyl ether, this means that in the compounds according to the invention, R 2 It is formed as follows: the epoxy ring of the diglycidyl ether is opened by the nitrogen atom, and then a ring with R is formed. 2The quaternary N atom adjacent to the group. Similarly, it is preferred when: R 2 Derived from diglycidyl ether, monodiglycidyl diglycidyl ether, ditriglycidyl diglycidyl ether, polyglycerols capped with glycidyl units, and poly(epoxyalkane) compounds capped with glycidyl units, particularly poly(ethylene oxide), poly(propylene oxide), and poly(butane oxide).

[0065] It is also preferred when the following is true: R 2 This compound is formed by esterifying a diol compound, such as an α,ω-diol or α,ω-dihydroxy polyether, particularly a dihydroxy-terminated poly(ethylene oxide), a dihydroxy-terminated poly(propylene oxide), or a dihydroxy-terminated poly(butane oxide), with a ω-halocarboxylic acid, particularly ω-chloroacetic acid or ω-chloropropionic acid. The latter compound is formed by the following process: R... 2 : Chlorine substituents are reacted with R 2 The N-atom adjacent to the group is substituted.

[0066] Based on this, it is preferred when: R 2 It is a C3-C50 alkylene group containing one or more internal ether or ester groups, and is particularly preferred when: R 2 These are alkylene groups having hydroxyl substituents.

[0067] When R 2 When it is a linear C1-C8 alkylene group without other substituents or functional groups, or when R 2 The preferred form is a linear C3-C50 alkylene group derived from diglycidyl ether, glycerol diglycidyl ether, monodiglycidyl diglycidyl ether, monodiethylene glycol diglycidyl ether, or ethylene glycol diglycidyl ether having 3-10 (ethylene oxide) repeating units.

[0068] Group R 6 They may be the same or different, selected from straight-chain, cyclic or branched, saturated or unsaturated hydrocarbon groups having 1 to 36 carbon atoms that are optionally substituted, and thus may represent hydrocarbon groups selected from: linear, branched or cyclic alkylene groups, linear, branched or cyclic alkenyl groups, linear, branched or cyclic alkyneyl groups, linear, branched or cyclic alkylene aryl groups, linear, branched or cyclic arylenealkyl groups and linear, branched or cyclic arylene groups, such as phenylene, benzylene or tolyl groups, particularly selected from such groups having 1 to 100 carbon atoms that each optionally contains one or more functional groups as shown above.

[0069] More preferably, R 6The group is selected from linear alkylene groups and linear alkenyl groups, particularly from linear C6-C24 alkylene groups such as hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecanylene, octadecylene, nonadecanylene, eicosylene, dodecylene, tridecylene, and tetradecylene, or linear C6-C24 alkenyl groups. Groups such as hexeneyl, heptenyl, octeneyl, noneneyl, deceneyl, undeceneyl, dodeceneyl, trideceneyl, tetradeceneyl, pentadeceneyl, hexadeceneyl, heptadeceneyl, heptadeceneyl, octadeceneyl, nonadeceneyl, icoseneyl, icoseneyl, icoseneyl, icoseneyl, icoseneyl, and tetradeceneyl are most preferably bonded to an adjacent C(O) group via a terminal C atom.

[0070] Regarding which C atom of the hydrocarbon group the adjacent C(O) group and X group are bonded to R. 6 There are no restrictions.

[0071] However, R 6 Preferably derived from hydroxycarboxylic acids having one or more hydroxy groups, more preferably derived from monohydroxycarboxylic acids, and most preferably derived from C7-C25 fatty acids having one hydroxy group as a substituent. Therefore, R 6 Preferably, it represents an alkylene or alkenylene chain of this type of carboxylic acid. For example, if R 6 Derived from ricinoleic acid

[0072]

[0073] Ricinoleic acid ((Z)-12-hydroxy-octadec-9-enoic acid),

[0074] Then R 6 It represents a 1,11-heptadec-8-ene group.

[0075]

[0076] 1,11-Heptadec-8-ene group

[0077] The "1,11" indicates the position where the group is bonded to the adjacent groups X and C(O).

[0078] At least one part of the cationic structure of general formula (I) contains R as defined by formula (III) or formula (IV). 6 Repeating unit (–X–C(O)–R) 6 ) or (–C(O)–X–R 6The quantity is 1-20, preferably 1-15, 1-12, 1-10, 1-8, or 2-20, 3-20, 4-20, 5-20, especially 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0079] Residue R 1 Preferred examples are C3-C18 polyether groups substituted with hydroxyl groups, particularly glycerol-based polyether groups, and C1-C8 linear alkyl or alkylene groups.

[0080] In this document, the term polyether specifically includes compounds derived from poly(epoxyalkane) (poly(alkylene oxide)), wherein the alkylene groups of the repeating unit are independently selected from C1-C8 alkylene groups.

[0081] Residue R 2 Preferred examples are linear C1-C8 alkylene groups, more preferably ethylene, propylene, butylene, pentylene, hexylene, and heptylene, and most preferably propylene and hexylene.

[0082] Residue R 3 R 4 and R 5 Preferred examples are linear C1-C8 alkyl groups and linear alkyl groups containing one or more moieties having formula (III) or (IV), wherein m is preferably 2-6, and most preferably R 3 R 4 and R 5 Independently selected from methyl groups and alkyl groups containing one or more portions of formula (III).

[0083] R 6 Preferred examples are structures derived from the corresponding hydroxycarboxylic acid by abstracting a carboxyl group and an OH group, wherein the hydroxycarboxylic acid is preferably selected from ricinoleic acid, lesquerolic acid, 10-hydroxyoctadecanoic acid, 12-hydroxyoctadecanoic acid, 14-hydroxytetradecanoic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or dihydroxycarboxylic acid, particularly 2,2'-di-hydroxymethylpropionic acid, 9,10-dihydroxystearic acid, or polyhydroxycarboxylic acid, particularly gluconic acid. Most preferably, R 6The compound is derived from hydroxyeicosenoic acid or ricinoleic acid in the manner described above. In both cases, naturally occurring enantiomers of the compound are particularly preferred, namely: (9Z,12R)-12-hydroxyoctadec-9-enoic acid obtained by saponification or fractionation of hydrolyzed castor oil (which is the seed oil of the castor plant); and (11Z,14R)-14-hydroxyeicosenoic acid isolated from species of the genera *Paysonia* and *Physaria*. However, according to the invention, racemic mixtures, the S-enantiomers and E-enantiomers of the compound, their racemic mixtures, enantiomers, and any possible mixtures are also preferred.

[0084] R 11 Preferred examples are C1-C10 alkyl groups, particularly methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentane, and n-hexyl groups, cyclopentyl and cyclohexyl groups, C2-C10 alkenyl groups, particularly vinyl and allyl groups, and C6–C12 aromatic groups, particularly phenyl, tolyl, and benzyl groups, wherein each of the named groups may be substituted with a hydroxyl group or a halogen group.

[0085] According to the present invention, the counter ion A of the ammonium ion according to the present invention - Selected from monovalent to trivalent inorganic or monovalent to 30,000-valent organic anions, preferably monovalent to 1,000-valent organic anions.

[0086] Among them, counterion A - Preferably, the anions are selected from halogen anions such as chloride, bromide, and iodide; inorganic oxyacid anions such as sulfate, phosphate, phosphonate, sulfonate, and methylsulfate; carboxylate anions such as acetate, propionate, lactate, octanoate, 2-ethylhexanoate, dodecanoate, hexadecanoate, octadecanoate, oleate, castor oil, 12-hydroxy-octadecanoate, succinate, maleate, and tartrate; polyether carboxylate anions; and polymeric fatty acid carboxylate anions of the following types:

[0087] R 1 [(-C(O)-XR 6 ) m -C(O)-XR 7 ] x ,or

[0088] R 1 [(XC(O)-R 6 ) m -XC(O)-R 7 ] x , where R 1 Or at least one R 7 Or R 1and at least one R 7 Both have one or more carboxylate groups.

[0089] Preferably, X = 0.

[0090] in particular

[0091] The following types of linear polymeric fatty acid carboxyl groups:

[0092] - OC(O)-R 6 (-XC(O)-R 6 ) m-1 -XC(O)-R 7 Preferably

[0093] - OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7 ,

[0094] That is, it is derived from linear polyfatty acid structures, for example

[0095]

[0096]

[0097] Branched linear polymeric fatty acid carboxyl groups

[0098] That is, it is derived from branched polyfatty acid structures, for example

[0099]

[0100] in

[0101]

[0102] in

[0103]

[0104] in

[0105]

[0106] ,in

[0107]

[0108] Or one of them

[0109]

[0110] Alternatively, branched linear polymeric fatty acid carboxyl groups derived from polyfunctional carboxylic acids, particularly dicarboxylic acid succinic acid and maleic acid with castor oil or lesquerella oil, such as...

[0111]

[0112] One of them

[0113]

[0114] And the remaining two

[0115]

[0116] Dendritic polymer type fatty acid carboxyl group,

[0117] That is, it is derived from dendritic polyfatty acid structures, for example

[0118]

[0119] in

[0120]

[0121] Or the following types of polymeric fatty acid carboxyl groups:

[0122] XR 6 (–C(O)–X–R 6 ) m-1 –C(O)–X–R 7 ,or

[0123] R 6 (–C(O)–X–R 6 ) m-1 –C(O)–X–R 7 ,

[0124] In the latter two types, R 7 The group has at least one anionic carboxylic acid ester group.

[0125] Or the following types of polymeric fatty acid carboxyl groups:

[0126] R 1 [(-C(O)-X-R6) m -C(O)O - ] x ,For example

[0127]

[0128] Among them, X and R 1 R 6 m and x are as defined above, and

[0129] R 7 Independently selected from optionally substituted straight-chain, cyclic, or branched, saturated or unsaturated hydrocarbon groups, having 1-36 carbon atoms, and optionally containing one or more groups selected from: –O–, –NH–, –C(O)–, –C(S)–, tertiary amine groups. Quaternary ammonium groups Furthermore, it can be substituted by OH groups or halogen groups, wherein group R 7 It cannot contain an internal carboxyl group or amide, i.e., R 7 It cannot contain a combination of –C(O)- and -O- groups, or a combination of -C(O)- and -NH- or tertiary amino groups.

[0130] And the counterion A of this group - Preferably, the valence is from monovalent to fiftievalent; more preferably, from monovalent to decavalent; even more preferably, from monovalent to pentavalent; most preferably, pentavalent, tetravalent, trivalent, divalent, or monovalent anions.

[0131] Alternatively, the counter anion may be selected from carboxylate anions based on poly(acrylic acid) homopolymers and copolymers.

[0132] That is, the carboxyl group derived from polyacrylic acid homopolymer.

[0133]

[0134] Where p = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 100010000.

[0135] Carboxylate anions derived from polyacrylic acid copolymers

[0136] That is, the polyacrylic acid copolymer contains non-reactive comonomers, such as...

[0137]

[0138] in

[0139] a = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000

[0140] b = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000 (this applies to all comonomers), where

[0141] The copolymer may have a block or random distribution of comonomer units.

[0142] Alternatively, it can be derived from the carboxylate anion of a polyacrylic acid copolymer containing a comonomer that provides OH and amine functional groups (which can be functionalized via additional ester or amide bonds, particularly with fatty acids or polyfatty acids), such as...

[0143]

[0144] Where c = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 100010000.

[0145] Or derived from carboxylate anions in polyacrylic acid copolymers containing comonomers with carboxylic acid functional groups, wherein

[0146] The copolymer may have a block or random distribution of comonomer units.

[0147] For example

[0148]

[0149] in

[0150] d = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000

[0151] e = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000 (this applies to all comonomers).

[0152] Based on maleic acid copolymers, particularly carboxyl groups derived from maleic anhydride copolymers, wherein

[0153] The copolymer may have a block or random distribution of comonomer units.

[0154] For example

[0155] in

[0156] f = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000 (this applies to all comonomers), and

[0157] g = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000.

[0158] Based on the carboxyl group of poly(itaconic acid) homopolymers and copolymers,

[0159] That is, it is derived from polyitacrylic acid homopolymer.

[0160]

[0161] Where h = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000.

[0162] Or derived from polyitaconic acid copolymers,

[0163] That is, the polyitaconic acid copolymer contains non-reactive comonomers, wherein

[0164] The copolymer may have a block or random distribution of comonomer units.

[0165] For example

[0166]

[0167] R x =CH3,R y =OCH3 Poly(methyl methacrylate-co-itaconic acid) PMIAA

[0168] R x =H,R y =NH2 poly(acrylamide-co-itaconic acid) PAIAA

[0169] in

[0170] i = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000 (this applies to all comonomers).

[0171] j = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000.

[0172] Alternatively, it can be derived from polyitaconic acid copolymers containing comonomers that provide OH and amine functional groups (which can be functionalized via additional ester or amide bonds, particularly with fatty acids or polyfatty acids), such as 2-hydroxyethyl methacrylate-itaconic acid copolymers.

[0173] Or it may be derived from polyitancolic acid copolymers containing comonomers with carboxylic acid functional groups, wherein

[0174] The copolymer may have a block or random distribution of comonomer units.

[0175] For example

[0176]

[0177] in

[0178] k = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000 (this applies to all comonomers).

[0179] l = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000.

[0180] The anion of the group is preferably divalent to 30,000 valence, more preferably 1,000 valence, even more preferably decavalent to 1,000 valence, even more preferably 50 valence to 1,000 valence, and most preferably 100 valence to 1,000 valence anion.

[0181] According to the present invention, any cationic structure according to the present invention can be combined with any anionic structure according to the present invention.

[0182] Preferably, a combination of a cation comprising a small number of quaternary nitrogen atoms, i.e., 1-20, particularly 1-10, more particularly 1-6 and even more particularly 1 or 2 quaternary nitrogen atoms, with a monovalent to decavalent anion, preferably a monovalent to hexavalent anion, more preferably a monovalent to trivalent anion, and even more preferably a monovalent or divalent anion.

[0183] Alternatively, polyanions with valences from one-to-three-thousand-valent, particularly polyanions with valences from one-to-one-thousand-valent or polyanions with valences from one hundred and one-thousand-valent can be used.

[0184] Polyquaternary ammonium cations comprising 21 or more quaternary nitrogen atoms are typically used with lower valence counterions, i.e., monovalent to fiftievalent anions, more preferably monovalent to decavalent anions, even more preferably monovalent to pentavalent anions, and most preferably monovalent and divalent counterions, particularly combinations of chloride anions, monocarboxylate anions, and dicarboxylate anions. The use of anions with a valence greater than 50 is less preferred herein.

[0185] As used above, R 7 Independently selected from optionally substituted straight-chain, cyclic, or branched, saturated or unsaturated hydrocarbon groups, having 1-36 carbon atoms, and optionally containing one or more groups selected from: –O–, –NH–, –C(O)–, –C(S)–, tertiary amine groups. Quaternary ammonium groups Furthermore, it can be substituted by OH groups or halogen groups, wherein group R 7 It cannot contain an internal carboxyl group or amide, i.e., R 7 It cannot contain a combination of –C(O)- groups and -O- groups, or a combination of –C(O)- groups and -NH- or tertiary amino groups.

[0186] According to the present invention, the group R 7 They may be the same or different, selected from linear, cyclic or branched, saturated or unsaturated hydrocarbon groups having 1 to 36 carbon atoms that are optionally substituted, and thus may represent hydrocarbon groups selected from linear, branched or cyclic alkyl groups, linear, branched or cyclic alkenyl groups, linear, branched or cyclic alkynyl groups, linear, branched or cyclic alkylaryl groups, linear, branched or cyclic aralkyl groups and linear, branched or cyclic aryl groups, such as phenyl, benzyl or tolyl, particularly selected from such groups having 6 to 24 carbon atoms that each optionally contains one or more functional groups as shown above.

[0187] More preferably, R 7 The group is selected from linear alkyl groups and linear alkenyl groups, particularly from linear C6-C24 alkyl groups such as hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, dodecyl, tridecyl, and tetradecyl, or linear C6-C24 alkenyl groups such as hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanenyl, eicosenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanenyl, eicosenyl, dodecenyl, tridecenyl, and tetradecenyl, wherein the group is most preferably bonded to an adjacent C(O) group or X group via a terminal C atom.

[0188] Regarding which C atom of the hydrocarbon group is adjacent to the C(O) group or X group bonded to R. 7 There are no restrictions.

[0189] However, R 7 Preferably derived from carboxylic acids or hydroxycarboxylic acids having one or more hydroxyl groups, more preferably derived from carboxylic acids or monohydroxycarboxylic acids, and most preferably derived from C7-C25 fatty acids without hydroxyl groups as substituents. Therefore, R 7 Preferably, it represents an alkyl or alkenyl chain of this type of carboxylic acid. For example, if R 7 Derived from ricinoleic acid

[0190]

[0191] Ricinoleic acid ((Z)-12-hydroxy-octadec-9-enoic acid),

[0192] Then R 7 It represents an 11-hydroxyheptadec-8-ene group.

[0193]

[0194] 11-hydroxy-heptadec-8-ene group,

[0195] Or if R 7 Derived from oleic acid,

[0196]

[0197] Oleic acid

[0198] Then R 7 It represents a heptadec-8-enyl group.

[0199]

[0200] Heptadec-8-ene group.

[0201] R 7 Preferred examples are structures derived from the corresponding carboxylic acid or hydroxycarboxylic acid by abstracting a carboxyl group, wherein the carboxylic acid may be selected from acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, grapeseed acid, caprylic acid, geranilic acid, caproic acid, terpenoid acid, capric acid, undecanoic acid, lauric acid, tridecanoic acid, myristic acid, pentadecanoic acid, palmitic acid, pearlitic acid, stearic acid, linoleic acid, α-linolenic acid, γ-linolenic acid, and nonadecanoic acid. Arachidonic acid, medelic acid, arachidonic acid, icosanoic acid, docosanoic acid, triicosanoic acid, and lignoceric acid, selected from hydroxycarboxylic acids such as hydroxyeicosenoic acid, ricinoleic acid, 10-hydroxyoctadecanoic acid, 12-hydroxyoctadecanoic acid, 14-hydroxytetradecanoic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or selected from dihydroxycarboxylic acids, especially 2,2'-di-hydroxymethylpropionic acid, 9,10-dihydroxystearic acid, or polyhydroxycarboxylic acids, especially gluconic acid.

[0202] Although group R 7 Optionally contains one or more groups selected from the following: –O–, –NH–, –C(O)–, –C(S)–, tertiary amine groups. Quaternary ammonium groups It can be substituted by OH groups or halogen groups, but group R 7 It cannot contain a combination of –C(O)- groups and –O- groups that form an internal carboxylic ester group, i.e., an internal ester group, or an internal amide group, or a combination of –C(O)- groups and –NH- or tertiary amino groups.

[0203] Considering the structure of equations (I) and (II) and R 1 R 2 R 3 R 4 and R 5 By definition, it is clear that in some cases, the substructure of the compound according to the invention may be assigned to residues R shown in formulas (I) and (II) and defined above in more than one manner. 1 R 2 R 3 R 4 and R 5 .

[0204] Only in such cases should the following rules be applied to clearly assign substructures to the term R in this order. 1 -R 5 :

[0205] -R 1 The selection should be made in such a way that the subscript x is bound to R. 1 The number of –(-F) groups should be as high as possible;

[0206] -R 1 The selection should be made in such a way that the number of groups F with n≠0 is as low as possible;

[0207] -If there are several options that satisfy the aforementioned requirements, R 1 The selection should be made in the following manner: R 1 The number of carbon atoms in it should be as high as possible;

[0208] -If there are still two or more substructures that satisfy the aforementioned requirements in the same way, R 1 The substructure should be selected in such a way that it is the substructure with the highest sum of atomic weights among all possible substructures.

[0209] Note that, according to the present invention, if several arbitrary residues R are present in the compound according to the present invention... 2 R 3 R 4 R 5 R 6 Or R 7 Each of the residues may represent another substructure as defined above, i.e., each R 2 R 3 R 4 R 6 and R 7 The groups are selected independently according to the definition according to the present invention.

[0210] In a preferred embodiment of the invention, compounds of the following formula as defined above are provided:

[0211] R 1 (–F) x (I)

[0212] Where x is between 2 and 50.

[0213] More preferably, according to this embodiment, x is in the following range: 3-50, 4-50, 5-50, 6-50, 7-50, 8-50, 9-50, 10-50, 2-40, 2-35, 2-30, 2-25, 2-20, 2-15 or 2-10.

[0214] In another preferred embodiment of the invention, compounds of the following general formulas as defined above do not include poly(ethylene oxide) or poly(propylene oxide) units.

[0215] R 1 (–F) x (I).

[0216] According to the present invention, a poly(ethylene oxide) unit is defined as a (CH2CH2O) unit in which x≥2. x The unit represented, and the poly(propylene oxide) unit defined as being composed of the formula (CH2CH(CH3)O) where x≥2. x The unit represented.

[0217] In a further preferred embodiment of the invention, in the general formula R as defined above... 1 (–F) x In compound (I), R 1 Contains at least one part having general formula (IIIa) or general formula (IVa):

[0218] (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa),

[0219] (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa)

[0220] Where X and R 6 And m as defined above, and

[0221] R 7Independently selected from optionally substituted straight-chain, cyclic, or branched, saturated or unsaturated hydrocarbon groups, having 1-36 carbon atoms, and optionally containing one or more groups selected from: –O–, –NH–, –C(O)–, –C(S)–, tertiary amine groups. Quaternary ammonium groups Furthermore, it can be substituted by OH groups or halogen groups, wherein group R 7 It cannot contain an internal carboxyl group or amide, i.e., R 7 It cannot contain a combination of –C(O)- groups and -O- groups, or a combination of –C(O)- groups and -NH- or tertiary amino groups.

[0222] According to this embodiment, group R 7 They may be the same or different, selected from linear, cyclic or branched, saturated or unsaturated hydrocarbon groups having 1 to 36 carbon atoms that are optionally substituted, and thus may represent hydrocarbon groups selected from linear, branched or cyclic alkyl groups, linear, branched or cyclic alkenyl groups, linear, branched or cyclic alkynyl groups, linear, branched or cyclic alkylaryl groups, linear, branched or cyclic aralkyl groups and linear, branched or cyclic aryl groups, such as phenyl, benzyl or tolyl, particularly selected from such groups having 6 to 24 carbon atoms that each optionally contains one or more functional groups as shown above.

[0223] More preferably, R 7 The group is selected from linear alkyl groups and linear alkenyl groups, particularly from linear C6-C24 alkyl groups such as hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, dodecyl, tridecyl, and tetradecyl, or linear C6-C24 alkenyl groups such as hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanenyl, eicosenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanenyl, octadecenyl, nonadecanenyl, eicosenyl, dodecenyl, tridecenyl, and tetradecenyl, wherein the group is most preferably bonded to the adjacent X group via a terminal C atom.

[0224] Regarding which C atom of the hydrocarbon group is the adjacent group X bonded to R. 7 There are no restrictions.

[0225] However, R 7 Preferably derived from carboxylic acids or hydroxycarboxylic acids having one or more hydroxyl groups, more preferably derived from carboxylic acids or monohydroxycarboxylic acids, and most preferably derived from C7-C25 fatty acids without hydroxyl groups as substituents. Therefore, R 7Preferably, it represents an alkyl or alkenyl chain of such a carboxylic acid, as shown above for group R. 7 As illustrated in the given examples.

[0226] According to the R of this embodiment 7 Preferred examples are structures derived from the corresponding carboxylic acid or hydroxycarboxylic acid by abstracting a carboxyl group, wherein the carboxylic acid may be selected from acetic acid, propionic acid, butyric acid, valeric acid, caprylic acid, gluconic acid, caprylic acid, geranic acid, caprylic acid, undecanoic acid, lauric acid, tridecanoic acid, myristic acid, pentadecanoic acid, palmitic acid, pearlitic acid, stearic acid, linoleic acid, α-linolenic acid, γ-linolenic acid, oleic acid, nonadecanoic acid, arachidic acid, meadic acid, arachidonic acid, icosanoic acid, dodecanoic acid, tridecanoic acid, and creosotenic acid; or from hydroxycarboxylic acids such as hydroxyeicosenoic acid, ricinoleic acid, 10-hydroxyoctadecanoic acid, 12-hydroxyoctadecanoic acid, 14-hydroxytetradecanoic acid, 10-hydroxystearic acid, 12-hydroxystearic acid; or from dihydroxycarboxylic acids, particularly 2,2'-di-hydroxymethylpropionic acid, 9,10-dihydroxystearic acid; or polyhydroxycarboxylic acids, particularly gluconic acid.

[0227] More preferably, R according to this embodiment 7 The group is derived from palmitic acid, pearlitic acid, stearic acid, linoleic acid, α-linolenic acid, γ-linolenic acid, oleic acid, nonadecanic acid, arachidic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, ricinoleic acid, hydroxyeicosenoic acid, or derived from 2,2'-di-hydroxymethylpropionic acid.

[0228] According to the most preferred embodiment R 7 The functional groups are oleic acid, stearic acid, hydroxyeicosenoic acid and ricinoleic acid.

[0229] Although group R 7 Optionally contains one or more groups selected from the following: –O–, –NH–, –C(O)–, –C(S)–, tertiary amine groups. Quaternary ammonium groups It can be substituted by OH groups or halogen groups, but group R 7 It cannot contain a combination of –C(O)- groups and –O- groups that form an internal carboxylic ester group, i.e., an internal ester group, or an internal amide group, or a combination of –C(O)- groups and –NH- or tertiary amino groups.

[0230] In a further preferred embodiment of the invention, in the general formula R as defined above... 1 (–F) x In compound (I), residue R 1 Or R 2 Only one or more of them contain at least one part having general formula (III) or (IV).

[0231] (–X–C(O)–R 6 ) m –X–C(O)– (III), or

[0232] (–C(O)–X–R 6 ) m –C(O)–X– (IV),

[0233] Preferably, residue R 1 Or R 2 One or more of which contain at least one part having general formula (IIIa) or general formula (IVa).

[0234] (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa),

[0235] (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa),

[0236] Among them, X and R 6 R 7 And m as defined above.

[0237] According to this embodiment, it is preferred when the following is true: in residue R 1 Or R 2 In the part having formula (IIIa) or (Iva)

[0238] X = O,

[0239] R 6 The groups are independently selected from hexene, heptene, octene, nonene, decene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecanylene, octadecylene, nonadecanylene, eicosylene, icosylene, icosylene, tridecylene, and tetradecylene, or hexene, heptene, octene, nonene, decene, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, icosylene, eicosylene, icosylene, icosylene, tridecenyl, icosylene, and tetradecenyl, preferably bonded to an adjacent C(O) group or O group via a terminal C atom.

[0240] R 7The group is independently selected from hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, dodecyl, tridecyl, and tetradecyl, or hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanenyl, eicosenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanenyl, eicosenyl, dodecenyl, tridecenyl, and tetradecenyl, wherein the group is most preferably bonded to an adjacent C(O) group via a terminal C atom.

[0241] m is 1-10, preferably 1, 2, 3, 4 or 5.

[0242] It is even more preferred when X = 0,

[0243] R 6 Selected from hexadecylene, heptadecanylene, octadecylene, nonadecanylene, eicosylene, hexadecenylene, heptadecanylene, octadecenylene, nonadecanylene, and eicosylene.

[0244] R 7 Selected from hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanenyl, and eicosenyl.

[0245] And m can be 1, 2, 3, 4 or 5.

[0246] According to this implementation, the following is the most preferred condition:

[0247] X = O,

[0248] R 6 Derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or hydroxyeicosenoic acid.

[0249] R 7 Derived from oleic acid, ricinoleic acid, or stearic acid

[0250] And m can be 1, 2, 3, 4 or 5.

[0251] In another preferred embodiment of the invention, in formula R as defined above 1 (–F) xIn the compound (I), at least 1% of all groups F contains at least one moiety having general formula (III) or (IV), more preferably at least 10% of all groups F contains at least one moiety having general formula (III) or (IV), even more preferably at least 50% of all groups F contains at least one moiety having general formula (III) or (IV), and most preferably 100% of all groups F contains at least one moiety having general formula (III) or (IV), or wherein at least 1% of all groups F contains at least one moiety having general formula (IIIa) or (IVa), more preferably at least 10% of all groups F contains at least one moiety having general formula (IIIa) or (IVa), even more preferably at least 50% of all groups F contains at least one moiety having general formula (IIIa) or (IVa), and most preferably 100% of all groups F contains at least one moiety having general formula (IIIa) or (IVa).

[0252] According to this embodiment, it is preferred that each portion of group F having general formula (III) or (IV) contains at least one R selected from the following: 6 Optionally substituted with hydroxyl groups: hexene, heptene, octene, nonene, decene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecanylene, octadecylene, nonadecanylene, icosylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, and tetradecylene, or hexenyl, hepteneyl, octeneyl, noneneyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanenyl, icosylene, dodecenyl, dodecenyl, tridecenyl, tetradecenyl, dodecenyl, tridecenyl, and tetradecenyl.

[0253] More preferably, each portion of group F having general formula (III) or (IV) contains at least one R selected from the following 6 Optionally substituted with hydroxyl groups: hexadecylene, heptadecanylene, octadecylene, nonadecanylene, eicosylene, hexadecenylene, heptadecanylene, octadecenylene, nonadecanylene, eicosylene.

[0254] And m is 1, 2, 3, 4 or 5, and most preferably R in each of the portions of the group F having general formula (III) or (IV). 6 Derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or hydroxyeicosenoic acid.

[0255] And m can be 1, 2, 3, 4 or 5.

[0256] In a further preferred embodiment of the invention, in formula R as defined above... 1 (–F) x In compound (I), all groups R 2 At least 1% of it contains at least one moiety having general formula (III) or (IV), more preferably all groups R 2 At least 10% of it contains at least one moiety having general formula (III) or (IV), and even more preferably all groups R 2 At least 50% of it contains at least one moiety having general formula (III) or (IV), and most preferably all groups R 2 100% of it contains at least one part having general formula (III) or (IV), or all of which contain R groups 2 At least 1% of it contains at least one moiety having the general formula (IIIa) or (IVa), more preferably at least 10% of all groups R 2 Contains at least one part having the general formula (IIIa) or (IVa), or more preferably all groups R 2 At least 50% of it contains at least one moiety having the general formula (IIIa) or (IVa), and most preferably all groups R 2 100% of it contains at least one part having the general formula (IIIa) or (IVa).

[0257] According to this embodiment, it is preferred when: group R 2 Each portion having general formula (III) or (IV) contains at least one R selected from the following 6 Optionally substituted with hydroxyl groups: hexene, heptene, octene, nonene, decene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecanylene, octadecylene, nonadecanylene, icosylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, and tetradecylene, or hexenyl, hepteneyl, octeneyl, noneneyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanenyl, icosylene, dodecenyl, dodecenyl, tridecenyl, tetradecenyl, dodecenyl, tridecenyl, and tetradecenyl.

[0258] It is more preferred when: group R 2 Each portion having general formula (III) or (IV) contains at least one R selected from the following 6Optionally substituted with hydroxyl groups: hexadecylene, heptadecanylene, octadecylene, nonadecanylene, eicosylene, hexadecenylene, heptadecanylene, octadecenylene, nonadecanylene, eicosylene.

[0259] And m is 1, 2, 3, 4 or 5, and

[0260] Most preferably, group R 2 R in each of the parts having general formula (III) or (IV) 6 Derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or hydroxyeicosenoic acid.

[0261] And m can be 1, 2, 3, 4 or 5.

[0262] In another preferred embodiment of the invention, in formula R as defined above 1 (–F) x In compound (I), all groups R 3 R 4 and R 5 At least 1% of it contains at least one moiety having general formula (III) or (IV), more preferably all groups R 3 R 4 and R 5 At least 10% of it contains at least one moiety having general formula (III) or (IV), and even more preferably all groups R 3 R 4 and R 5 At least 50% of it contains at least one moiety having general formula (III) or (IV), and most preferably all groups R 3 R 4 and R 5 100% of it contains at least one part having general formula (III) or (IV), or all of which contain R groups 3 R 4 and R 5 At least 1% of it contains at least one moiety having the general formula (IIIa) or (IVa), more preferably all groups R 3 R 4 and R 5 At least 10% of it contains at least one moiety having the general formula (IIIa) or (IVa), and even more preferably all groups R 3 R 4 and R 5 At least 50% of it contains at least one moiety having the general formula (IIIa) or (IVa), and most preferably all groups R 3 R 4 and R 5100% of it contains at least one part having the general formula (IIIa) or (IVa).

[0263] According to this embodiment, it is preferred when: group R 3 R 4 and R 5 Each portion having general formula (III) or (IV) contains at least one R selected from the following 6 Optionally substituted with hydroxyl groups: hexene, heptene, octene, nonene, decene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecanylene, octadecylene, nonadecanylene, icosylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, and tetradecylene, or hexenyl, hepteneyl, octeneyl, noneneyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanenyl, icosylene, dodecenyl, dodecenyl, tridecenyl, tetradecenyl, dodecenyl, tridecenyl, and tetradecenyl.

[0264] It is more preferred when: group R 3 R 4 and R 5 Each portion having general formula (III) or (IV) contains at least one R selected from the following 6 Optionally substituted with hydroxyl groups: hexadecylene, heptadecanylene, octadecylene, nonadecanylene, eicosylene, hexadecenylene, heptadecanylene, octadecenylene, nonadecanylene, eicosylene.

[0265] And m is 1, 2, 3, 4 or 5, and

[0266] Most preferably, group R 3 R 4 and R 5 R in each of the parts having general formula (III) or (IV) 6 Derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or hydroxyeicosenoic acid.

[0267] And m can be 1, 2, 3, 4 or 5.

[0268] In yet another preferred embodiment of the invention, in the general formula R as defined above... 1 (–F) x In compound (I),

[0269] x is 2 and the compound has the general formula (V):

[0270]

[0271] Where R 1 R 2 R 3 R 4 R 5 And n as defined above.

[0272] In a preferred embodiment of the invention, compounds of the following formula as defined above are provided:

[0273] R 1 (–F) x (I), where

[0274] R 1 The hydrocarbon group is selected from monovalent to fiftievalent, optionally substituted, having up to 1000 carbon atoms, preferably 2-300 carbon atoms, more preferably 3-200 carbon atoms, even more preferably 3-150 carbon atoms, particularly 3-50 carbon atoms, and even more particularly 3-20 carbon atoms, and may optionally contain one or more groups selected from: –O–, –NH–, –C(O)–, –C(S)–, tertiary amine groups. The group can be substituted with –OH groups and halogen groups, preferably R 1 It is a C3-C18 glycerol-based polyether group or a C1-C8 linear alkylene group, and

[0275] F has a general form (VI), which is consistent with form (II) where n equals 0:

[0276]

[0277] And the group F binds to R 1 carbon atoms,

[0278] in

[0279] R 3 R 4 R 5 Independently selected from hydrogen, and optionally substituted straight-chain, cyclic, or branched, saturated, unsaturated, or aromatic hydrocarbon groups, having up to 300 carbon atoms, preferably 1-200 carbon atoms, more preferably 1-150 carbon atoms, even more preferably 1-50 carbon atoms, particularly 1-20 carbon atoms, and even more particularly 1-10 carbon atoms, optionally containing one or more groups selected from: –O–, –NH–, –C(O)–, –C(S)–, tertiary amine groups. Quaternary ammonium groups And it can be substituted with OH, preferably R. 3 -R 5It is a C1-C8 linear alkyl group such as methyl, ethyl, propyl or butyl, or a linear alkyl group containing one or more moieties of general formula (III) or (IV), more preferably a linear alkyl group terminated by a group of general formula (IIIa) or (IVa).

[0280] Counterion A - The anions are selected from monovalent to trivalent inorganic anions and monovalent to 30,000-valent, preferably monovalent to 1,000-valent organic anions, and preferably selected from halide anions such as chloride, bromide, iodide, sulfate, phosphate, phosphonate, sulfonate, methylsulfate, and carboxyl anions such as acetate, propionate, lactate, octanoate, 2-ethylhexanoate, dodecanoate, hexadecanoate, octadecanoate, oleate, castor oil, 12-hydroxy-octadecanoate, succinate, maleate, tartrate, polyether carboxylates, and polymeric fatty acid carboxylates of the following types:

[0281] R 1 [(-C(O)-XR 6 ) m -C(O)-XR 7 ] x ,or

[0282] R 1 [(XC(O)-R 6 ) m -XC(O)-R 7 ] x , where R 1 Or at least one R 7 Or R 1 and at least one R 7 Both have one or more carboxylate groups.

[0283] Preferably, where X = 0,

[0284] in particular

[0285] -The following types of linear polymeric fatty acid carboxyl groups:

[0286] - OC(O)-R 6 (-XC(O)-R 6 ) m-1 -XC(O)-R 7 Preferably

[0287] - OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7 ,

[0288] That is, it is derived from the linear polyfatty acid structure.

[0289] - Branched linear polymeric fatty acid carboxyl groups

[0290] That is, it is derived from the branched polyfatty acid structure.

[0291] In particular, branched linear polymeric fatty acid carboxyl groups derived from polyfunctional carboxylic acids, especially dicarboxylic acid succinic acid and maleic acid with castor oil or Resclere oil, such as...

[0292]

[0293] One of them

[0294] And the remaining two

[0295] - Dendritic polymeric fatty acid carboxyl groups,

[0296] That is, it is derived from the dendritic polyfatty acid structure.

[0297] Or the following types of polymeric fatty acid carboxyl groups:

[0298] XR 6 (–C(O)–X–R 6 ) m-1 –C(O)–X–R 7 ,or

[0299] R 6 (–C(O)–X–R 6 ) m-1 –C(O)–X–R 7 ,

[0300] In the latter two types, R 7 The group has at least one anionic carboxylate group.

[0301] Or the following types of polymeric fatty acid carboxyl groups:

[0302] R 1 [(-C(O)-X-R6) m -C(O)O - ] x ,

[0303] And among them X, R 1 R 6 R 7 m and x are as defined above

[0304] The counter ion A of this group - Preferably, the valence is monovalent to fiftievalent, more preferably monovalent to decavalent, even more preferably monovalent to pentavalent, and most preferably pentavalent, tetravalent, trivalent, divalent, or monovalent anions.

[0305] Alternatively, the counter anion may be selected from carboxylate anions based on poly(acrylic acid) homopolymers and copolymers.

[0306] That is, the carboxyl group derived from the following homopolymers of polyacrylic acid.

[0307]

[0308] Where p = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000.

[0309] Carboxylate anions derived from polyacrylic acid copolymers

[0310] That is, the polyacrylic acid copolymer contains non-reactive comonomers, such as...

[0311]

[0312] in

[0313] a = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000

[0314] b = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000 (this applies to all comonomers), where

[0315] The copolymer may have a block or random distribution of comonomer units.

[0316] Alternatively, it can be derived from the carboxylate anion of a polyacrylic acid copolymer containing a comonomer that provides OH and amine functional groups (which can be functionalized via additional ester or amide bonds, particularly with fatty acids or polyfatty acids), such as...

[0317]

[0318] Where c = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000.

[0319] Or derived from carboxylate anions in polyacrylic acid copolymers containing comonomers with carboxylic acid functional groups, wherein

[0320] The copolymer may have a block or random distribution of comonomer units.

[0321] For example

[0322]

[0323] in

[0324] d = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000

[0325] e = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000 (this applies to all comonomers).

[0326] Based on maleic acid copolymers, particularly carboxyl groups derived from maleic anhydride copolymers, wherein

[0327] The copolymer may have a block or random distribution of comonomer units.

[0328] For example

[0329]

[0330] in

[0331] f = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000 (this applies to all comonomers), and

[0332] g = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000.

[0333] Based on the carboxyl group of poly(itaconic acid) homopolymers and copolymers,

[0334] That is, it is derived from polyitacrylic acid homopolymer.

[0335]

[0336] Where h = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000.

[0337] Or derived from poly(itaconic acid) copolymers,

[0338] That is, the poly(itaconic acid) copolymer contains non-reactive comonomers, wherein

[0339] The copolymer may have a block or random distribution of comonomer units.

[0340] For example

[0341]

[0342] R x =CH3,R y =OCH3 Poly(methyl methacrylate-co-itaconic acid) PMIAA

[0343] R x =H,R y =NH2 poly(acrylamide-co-itaconic acid) PAIAA

[0344] in

[0345] i = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000 (this applies to all comonomers).

[0346] j = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000.

[0347] Alternatively, it can be derived from polyitanconic acid copolymers containing comonomers that provide OH and amine functional groups (which can be functionalized via additional ester or amide bonds, particularly with fatty acids or polyfatty acids), such as 2-hydroxyethyl methacrylate-itanconic acid copolymers.

[0348] Alternatively, it can be derived from polyitanconic acid copolymers containing comonomers with carboxylic acid functional groups, wherein...

[0349] The copolymer may have a block or random distribution of comonomer units.

[0350] For example

[0351]

[0352] in

[0353] k = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000 (this applies to all comonomers).

[0354] l = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000.

[0355] The anion of this group is preferably divalent to 30,000 valence, more preferably divalent to 1,000 valence, even more preferably decavalent to 1,000 valence, even more preferably fiftievalent to 1,000 valence, and most preferably 100 valence to 1,000 valence anion.

[0356] The condition is that the group R of the cationic structure of general formulas (I) and (II) 1 R 3 R 4 R 5 To a portion containing at least one part having the general formula (IIIa) or (IVa):

[0357] (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa)

[0358] (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa)

[0359] Where X is as defined above.

[0360] m = 1-20, preferably 1-10, more preferably 1-6, even more preferably 2-6, especially 1, 2, 3, 4, 5, 6, and

[0361] R 11 Preferably selected from: hydrogen, normal, iso, or tertiary C1-C 22 -alkyl, C2-C 22 -Alkoxyalkyl, C5-C 30 -Cycloalkyl, C6-C 30 -Aryl, C6-C 30 -Aryl (C1-C6)alkyl, C6-C 30 -alkylaryl, C2-C 22 -Alkenyl, C2-C 22 -Alkenyloxyalkyl, optionally substituted with hydroxyl and halogen respectively, and optionally containing one or more ether groups (–O–); preferably hydrogen or normal, iso, or tertiary C1-C 22 -alkyl,

[0362] R 6 Independently selected from optionally substituted straight-chain, cyclic, or branched, saturated or unsaturated hydrocarbon groups, having 1-36 carbon atoms, preferably 1-24 carbon atoms, more preferably 1-18 carbon atoms, and even more preferably 8-18 carbon atoms, preferably R 6 It is a C6-C24 linear alkylene or alkenylene group, most preferably derived from ricinoleic acid or hydroxyeicosenoic acid.

[0363] R 7 Independently selected straight-chain, cyclic, or branched, saturated or unsaturated hydrocarbon groups, optionally substituted, having 1-36 carbon atoms, preferably 1-24 carbon atoms, more preferably 1-18 carbon atoms, and even more preferably 8-18 carbon atoms, optionally containing one or more groups selected from: –O–, –NH–, –C(O)–, –C(S)–, tertiary amine groups. Quaternary ammonium groups Furthermore, it can be substituted by OH groups or halogen groups, wherein group R 7 It cannot contain a combination of –C(O)- groups and –O- groups, or a combination of –C(O)- groups and –NH- or tertiary amino groups that form an internal carboxylic ester group or an internal amide group. Preferably, R 7 It is a C6-C24 alkyl or alkenyl group, more preferably a linear C12-C24 alkyl or C12-C24 alkenyl group, and most preferably derived from linoleic acid, linolenic acid, or oleic acid.

[0364] The condition is that at least one R 6 Having more than 6 carbon atoms, and

[0365] For x = 1

[0366] R 1 R 3 R 4 R 5 Nitrogen atoms that do not bind to the following groups via –OCH2CH2–

[0367]

[0368] In a further preferred embodiment of the invention, a compound of the following formula is provided:

[0369] R 1 (–F) x (I), where

[0370] R 1 The substituted hydrocarbon group is selected from monovalent to fiftievalent, preferably monovalent to thirtieth valent, more preferably monovalent to twentieth valent, even more preferably monovalent to decavalent, particularly monovalent, divalent, trivalent, tetravalent, pentavalent, hexavalent, heptavalent, octavalent, nonavalent, and decavalent, having up to 1000 carbon atoms, preferably 2-300 carbon atoms, more preferably 3-200 carbon atoms, even more preferably 3-150 carbon atoms, particularly 3-50 carbon atoms, and even more particularly 3-20 carbon atoms, and may optionally contain one or more groups selected from: –O–, –NH–, –C(O)–, –C(S)–, and tertiary amine groups. Quaternary ammonium groups And it can be substituted by –OH, and

[0371] F has the general formula (VI):

[0372]

[0373] And the group F binds to R 1 carbon atoms,

[0374] in

[0375] R 3 R 4 R 5 The carbon group is selected from optionally substituted straight-chain, cyclic, or branched, saturated, unsaturated, or aromatic hydrocarbon groups, having up to 300 carbon atoms, preferably 1-200 carbon atoms, more preferably 1-150 carbon atoms, even more preferably 1-50 carbon atoms, particularly 1-20 carbon atoms, and even more particularly 1-10 carbon atoms, and optionally contains one or more groups selected from: –O–, –NH–, –C(O)–, –C(S)–, tertiary amine groups. Quaternary ammonium groups And it can be replaced by OH.

[0376] Counterion A - The anions are selected from monovalent to trivalent inorganic anions and monovalent to 30,000-valent, especially monovalent to 1,000-valent organic anions, preferably from halide anions such as chloride, bromide, iodide, sulfate, phosphate, phosphonate, sulfonate, methylsulfate, and carboxyl anions such as acetate, propionate, lactate, octanoate, 2-ethylhexanoate, dodecanoate, hexadecanoate, octadecanoate, oleate, ricinoleate, 12-hydroxy-octadecanoate, succinate, maleate, tartrate, and polyether carboxylates.

[0377] The following types of polymeric fatty acid carboxyl groups:

[0378] R 1 [(-C(O)-XR 6 ) m -C(O)-XR 7 ] x ,or

[0379] R 1 [(XC(O)-R 6 ) m -XC(O)-R 7 ] x , where R 1 Or at least one R 7 Or R 1 and at least one R7 Both have one or more carboxylate groups.

[0380] Preferably, where X = 0,

[0381] in particular

[0382] -The following types of linear polymeric fatty acid carboxyl groups:

[0383] - OC(O)-R 6 (-XC(O)-R 6 ) m-1 -XC(O)-R 7 Preferably

[0384] - OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7 ,

[0385] That is, it is derived from the linear polyfatty acid structure.

[0386] - Branched linear polymeric fatty acid carboxyl groups

[0387] That is, it is derived from branched polyfatty acid structures, particularly from branched linear polymeric fatty acid carboxyl groups derived from polyfunctional carboxylic acids (especially dicarboxylic acid succinic acid and maleic acid) and esters of castor oil or Resclere oil, such as...

[0388]

[0389] One of them

[0390]

[0391] And the remaining two

[0392]

[0393] - Dendritic polymeric fatty acid carboxyl groups,

[0394] That is, it is derived from the dendritic polyfatty acid structure s.

[0395] Or the following types of polymeric fatty acid carboxyl groups:

[0396] XR 6 (–C(O)–X–R 6 ) m-1 –C(O)–X–R 7 ,or

[0397] R 6 (–C(O)–X–R 6 ) m-1 –C(O)–X–R 7 ,

[0398] In the latter two types, R 7 The group has at least one anionic carboxylate group.

[0399] Or the following types of polymeric fatty acid carboxyl groups:

[0400] R 1 [(-C(O)-X-R6) m -C(O)O - ] x ,

[0401] And among them X, R 1 R 6 R 7 m and x are as defined above, and

[0402] The counter ion A of this group - Preferably, the antagonistic ion is a monovalent to fiftievalent anion, more preferably a monovalent to decavalent anion, even more preferably a monovalent to pentavalent anion, most preferably a pentavalent, tetravalent, trivalent, divalent, or monovalent anion, or the counter ion is selected from carboxyl anions based on poly(acrylic acid) homopolymers and copolymers, i.e., carboxyl anions derived from the following polyacrylic acid homopolymers.

[0403]

[0404] Where p = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000.

[0405] Carboxylate anions derived from polyacrylic acid copolymers

[0406] That is, the polyacrylic acid copolymer contains non-reactive comonomers, such as...

[0407]

[0408] in

[0409] a = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000

[0410] b = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000 (this applies to all comonomers), where

[0411] The copolymer may have a block or random distribution of comonomer units.

[0412] Alternatively, it can be derived from the carboxylate anion of a polyacrylic acid copolymer containing a comonomer that provides OH and amine functional groups (which can be functionalized via additional ester or amide bonds, particularly with fatty acids or polyfatty acids), such as...

[0413]

[0414] Where c = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000.

[0415] Or derived from carboxylate anions in polyacrylic acid copolymers containing comonomers with carboxylic acid functional groups, wherein

[0416] The copolymer may have a block or random distribution of comonomer units.

[0417] For example

[0418]

[0419] in

[0420] d = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000

[0421] e = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000 (this applies to all comonomers).

[0422] Based on maleic acid copolymers, particularly carboxyl groups derived from maleic anhydride copolymers, wherein

[0423] The copolymer may have a block or random distribution of comonomer units.

[0424] For example

[0425]

[0426] in

[0427] f = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000 (this applies to all comonomers), and

[0428] g = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000.

[0429] Based on the carboxyl group of poly(itaconic acid) homopolymers and copolymers,

[0430] That is, it is derived from polyitacrylic acid homopolymer.

[0431]

[0432] Where h = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000.

[0433] Or it may be derived from polyitacrylic acid copolymers.

[0434] That is, the polyitaconic acid copolymer contains non-reactive comonomers, wherein

[0435] The copolymer may have a block or random distribution of comonomer units.

[0436] For example

[0437]

[0438] R x =CH3,R y =OCH3 Poly(methyl methacrylate-co-itaconic acid) PMIAA

[0439] R x =H,R y =NH2 poly(acrylamide-co-itaconic acid) PAIAA

[0440] in

[0441] i = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000 (this applies to all comonomers).

[0442] j = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000.

[0443] Alternatively, it can be derived from polyitanconic acid copolymers containing comonomers that provide OH and amine functional groups (which can be functionalized via additional ester or amide bonds, particularly with fatty acids or polyfatty acids), such as 2-hydroxyethyl methacrylate-itanconic acid copolymers.

[0444] Or it may be derived from polyitancolic acid copolymers containing comonomers with carboxylic acid functional groups, wherein

[0445] The copolymer may have a block or random distribution of comonomer units.

[0446] For example

[0447]

[0448] in

[0449] k = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000 (this applies to all comonomers).

[0450] l = 2-10000, preferably 10-10000, more preferably 100-10000, and even more preferably 1000-10000.

[0451] The anion of this group is preferably divalent to 30,000 valence, more preferably divalent to 1,000 valence, even more preferably decavalent to 1,000 valence, and most preferably 100 valence to 1,000 valence anion.

[0452] The condition is that the group R in the cationic structure of formulas (I) and (II) 1 R 3 R 4 R 5 At least one of them contains at least one part having the general formula (VII) or (VIII):

[0453] -XC(O)-R x -(XC(O)-R x ) m-1 -XC(O)-R 7 (VII), or

[0454] -XC(O)-R x -(XC(O)-R x ) m -XC(O)-R 7 (VIII)

[0455] in

[0456] X is O or NR 11 ,

[0457] m = 1-20, preferably 1-10, more preferably 1-6, even more preferably 2-6, especially 1, 2, 3, 4, 5, 6, and

[0458] R x +R 7 The total number of carbon atoms in (∑carbon atoms R) x R 7The value is 19-300, preferably 25-300, more preferably 35-300, even more preferably 50-300, particularly 35-200, even more particularly 35-150, even more particularly 50-150.

[0459] R 11 Preferably selected from hydrogen, ortho, iso, or tertiary C1-C 22 -alkyl, more preferably hydrogen

[0460] R x To be optionally subjected to OH, -OC(O)-R 7 -OC(O)-R 6 -(OC(O)-R 6 ) 0-19 -OC(O)-R 7 The substituted linear, cyclic, or branched, saturated or unsaturated hydrocarbon group has 1-36 carbon atoms, preferably 1-24 carbon atoms, more preferably 1-18 carbon atoms, and even more preferably 8-18 carbon atoms, preferably derived from monohydroxycarboxylic acids, especially glycolic acid, lactic acid, 2-hydroxybutyric acid, 3-hydroxybutyric acid, 4-hydroxybutyric acid, 14-hydroxytetradecanoic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, hydroxyeicosenoic acid, ricinoleic acid, or dihydroxycarboxylic acids, especially 2,2'-di-hydroxymethylpropionic acid, 9,10-dihydroxystearic acid, or polyhydroxycarboxylic acids, especially gluconic acid.

[0461] R 6 As defined above,

[0462] R 7 The optional substituted linear, cyclic, or branched, saturated or unsaturated hydrocarbon group has 1-36 carbon atoms, preferably 1-24 carbon atoms, more preferably 1-18 carbon atoms, and even more preferably 8-18 carbon atoms, preferably derived from acetic acid, octanoic acid, nonanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, eicosanoic acid, docosanoic acid, 2-ethylhexanoic acid, 2,2-dimethylpropionic acid, 2,2-dimethylheptanoic acid, 2,2-dimethyloctanoic acid, neodecanoic acid, undecano-10-enoic acid, oleic acid, linoleic acid, linolenic acid, and erucic acid.

[0463] According to this embodiment, it is preferred when: R 6The group independently selected from hexane, heptane, octane, nonane, decane, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecanylene, octadecylene, nonadecanylene, eicosylene, dodecylene, tridecylene, and tetradecylene, or hexenyl, heptenyl, octaneyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, and tetradecenyl, optionally substituted with a hydroxyl group. The compounds are tetradecene-alkenyl, pentadecene-alkenyl, hexadecene-alkenyl, heptadecene-alkenyl, octadecene-alkenyl, nonadecene-alkenyl, eicosene-alkenyl, icosene-alkenyl, icosene-alkenyl, icosene-alkenyl, triadecene-alkenyl, and tetradecene-alkenyl, more preferably independently selected from hexadecene, heptadecanyl, octadecene, nonadecene, eicosene, hexadecene-alkenyl, heptadecene-alkenyl, octadecene-alkenyl, nonadecene-alkenyl, and eicosene-alkenyl, most preferably each R 6 It is independently derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid or hydroxyeicosenoic acid.

[0464] In a further preferred embodiment of the invention, compounds of the following formula as defined above are provided:

[0465] R 1 (–F) x (I), where

[0466] R 1 Selected from:

[0467] - Straight-chain, cyclic, or branched, saturated, unsaturated, or aromatic hydrocarbon groups optionally substituted with OH or amide groups, ranging from monovalent to octavalent, preferably divalent to octavalent, more preferably divalent to hexavalent, and even more preferably divalent, trivalent, and tetravalent: derived from tertiary amines having at least three, preferably more than three carbon atoms, particularly trimethylamine, triethylamine, tributylamine, N,N-dimethylethanolamine, N,N-dimethylpropanolamine, N-methylimidazole, N,N,N',N'-tetramethyl-1,2-diaminoethane, N,N,N',N'-tetramethyl-1,4-diaminobutane, N,N,N',N'-tetramethyl-1,6-diaminohexane, N,N,N' N”,N”-pentamethyl-diethylenetriamine, N,N,N',N”,N”-pentamethyl-dipropylenetriamine, bis-(2-dimethylaminoethyl) ether, bis-(2-dimethylaminopropyl) ether, 2,2'-dimorpholinodiethyl ether, N,N-bis-(3-dimethylaminopropyl)-N-isopropanolamine, N,N,N'-trimethylaminoethyl-ethanolamine, 1,3,5-tris(3-(dimethylamino)propyl)-hexahydro-s-triazine; condensation products of epoxides, especially with alcohols (especially methanol, ethanol, 2-propanol, 1-butanol, tert-butanol, undec-10-enol, oleyl alcohol, stearyl alcohol, 1,2-propanediol, 1,3-propanediol, 1 3-Butanediol, 1,4-Butanediol, 1,2-Hexanediol, 1,6-Hexanediol, glycerol, diglycerol, triglycerides and higher linear or branched oligoglycerides, trimethylolpropane, castor oil (ricinoleic triglyceride), pentaerythritol, sorbitol, poly(epoxyalkane) such as polyethers based on (ethylene oxide), (propylene oxide) and / or (butane oxide) (e.g. derived from polyethylene glycol such as diethylene glycol, triethylene glycol, tetraethylene glycol and pentaethylene glycol, etc., or derived from polypropylene glycol such as dipropylene glycol (e.g., derived from 2,2′-oxydi-1-propanol, 1,1′-oxydi-2-propanol, and 2-(2-hydroxypropoxy)- 1-Propanol), tripropylene glycol, tetrapropylene glycol, pentapropylene glycol, glycidyl ethers derived from mixed (ethylene oxide) and (butane) coethers, coethers derived from mixed (propylene oxide) and (butane) coethers, and glycidyl ethers derived from mixed (ethylene oxide) and (propylene oxide) and (butane) coethers; or preferably glycidyl esters with acids, especially neodecanoic acid; condensation products with primary or secondary amino-functionalized amines (especially N,N-dimethylpropylenediamine, N,N,N',N'-tetramethyl-diethylenetriamine, N,N,N',N'-tetramethyl-dipropylenetriamine, N-methylmorpholine, N-methylpiperazine); and

[0468] - Straight-chain, cyclic, or branched, saturated, unsaturated, or aromatic hydrocarbon groups optionally substituted with OH, amino, or amide, having a monovalent to octavalent, preferably divalent to octavalent, more preferably divalent to hexavalent, and even more preferably divalent, trivalent, and tetravalent valence: derived from alkyl halides having more than one, preferably more than two, carbon atoms, such as alkyl chlorides, bromides, iodides, for example 1,3-dichloropropane, 1,3-dichlorobutane, 1,4-dichlorobutane, dichloro-monohydroxypropane isomers, 1,2,3-trichloropropane, 1,2-dichlorohexanediol, 1,2-dichlorohexane, or corresponding brominated and iodinated derivatives;

[0469] - Straight-chain, cyclic, or branched, saturated, unsaturated, or aromatic hydrocarbon groups optionally substituted with OH, amino, or amide groups, ranging from monovalent to octavalent, preferably divalent to octavalent, more preferably divalent to hexavalent, and even more preferably divalent, trivalent, and tetravalent: esters derived from halogenated carboxylic acids, preferably chlorocarboxylic acids (the total number of carbon atoms in the esters exceeds two, preferably more than three), such as chloroacetic acid, 3-chloropropionic acid, 4-chlorobutyric acid, or esters of corresponding bromocarboxylic acids with alcohols, particularly methanol, ethanol, 2-propanol, 1-butanol, tert-butanol, undecyl-10-enol, oleyl alcohol, stearyl alcohol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,2-hexanediol, 1,6-hexanediol, glycerol, diglycerol, triglycerides, and higher linear or branched oligoglycerols, trimethylolpropane. Castor oil (ricinoleic acid triglyceride), pentaerythritol, sorbitol, poly(epoxyalkane) such as polyethers based on (ethylene oxide), (propylene oxide) and / or (butane) (e.g., derived from polyethylene glycol such as diethylene glycol, triethylene glycol, tetraethylene glycol, and pentaethylene glycol, or derived from polypropylene glycol such as dipropylene glycol (e.g., derived from 2,2′-oxydi-1-propanol, ... 1,1′-oxydi-2-propanol, and 2-(2-hydroxypropoxy)-1-propanol), tripropylene glycol, tetrapropylene glycol, pentapropylene glycol, derived from coethers based on mixtures of (ethylene oxide) and (butane), derived from coethers based on mixtures of (propylene oxide) and (butane), and derived from coethers based on mixtures of (ethylene oxide) and (propylene oxide) and (butane).

[0470] - The following linear, cyclic, or branched, saturated, unsaturated, or aromatic hydrocarbon groups optionally substituted with OH, ranging from monovalent to octavalent, preferably divalent to octavalent, more preferably divalent to hexavalent, and even more preferably divalent, trivalent, and tetravalent: derived from ethers or esters of epoxides having a total of more than three, preferably more than four, carbon atoms, preferably with alcohols (especially methanol, ethanol, 2-propanol, 1-butanol, tert-butanol, undecyl-10-enol, oleyl alcohol, stearyl alcohol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,2-hexanediol, 1,6-hexanediol, glycerol, diglycerol, ditriglycerol, and higher linear or branched oligoglycerols, trimethylolpropane, castor oil (ricinoleic triglyceride), pentaerythritol, sorbitol, poly(epoxides), for example based on ( Polyethers of ethylene oxide, propylene oxide, and / or butane oxide (e.g., derived from polyethylene glycols such as diethylene glycol, triethylene glycol, tetraethylene glycol, and pentaethylene glycol, or derived from polypropylene glycols such as dipropylene glycol (e.g., derived from 2,2′-oxydi-1-propanol, 1,1′-oxydi-2-propanol, and 2-(2-hydroxypropoxy)-1-propanol) Di(tripropylene glycol), tri(tetrapropylene glycol), tetra(pentapropylene glycol), glycidyl ethers derived from mixed (ethylene oxide) and (butane) coethers, coethers derived from mixed (propylene oxide) and (butane) coethers, and glycidyl ethers derived from mixed (ethylene oxide), (propylene oxide), and (butane) coethers, or preferably glycidyl esters with acids, particularly neodecanoic acid.

[0471] - A straight-chain, cyclic, or branched, saturated, unsaturated, or aromatic hydrocarbon group optionally substituted with OH, amino, or amide, having a total of more than two, preferably more than three carbon atoms: ... The ester formation of the ester, wherein the ether or ester of the epoxide is preferably with an alcohol (especially methanol, ethanol, 2-propanol, 1-butanol, tert-butanol, undecyl-10-enol, oleyl alcohol, stearyl alcohol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,2-hexanediol, 1,6-hexanediol, glycerol, diglycerol, triglycerides, and higher linear or branched oligoglycerides, trimethylolpropane, castor oil (castor) Sesame oil triglyceride), pentaerythritol, sorbitol, poly(epoxyalkane), such as polyethers based on (ethylene oxide), (propylene oxide) and / or (butane oxide), particularly derived from polyethylene glycols such as diethylene glycol, triethylene glycol, tetraethylene glycol, and pentaethylene glycol, or derived from polypropylene glycols such as dipropylene glycol (particularly derived from 2,2′-oxydi-1-propanol, 1,1′-oxydi-2-propanol, and 2... -(2-hydroxypropoxy)-1-propanol), tripropylene glycol, tetrapropylene glycol, pentapropylene glycol, glycidyl ethers derived from mixed (ethylene oxide) and (butane) coethers, coethers derived from mixed (propylene oxide) and (butane) coethers, and glycidyl ethers derived from mixed (ethylene oxide) and (propylene oxide) and (butane) coethers, or preferably glycidyl esters with acids, particularly neodecanoic acid.

[0472] - A straight-chain, cyclic, or branched, saturated, unsaturated, or aromatic hydrocarbon group optionally substituted with OH, having a monovalent to octavalent, preferably divalent to octavalent, more preferably divalent to hexavalent, and even more preferably divalent, trivalent, and tetravalent valence: formed from an ether, preferably a glycidyl ether, of an epoxy compound having a total of more than seven, preferably more than eight carbon atoms, and a divalent to hexavalent carboxylic acid, particularly maleic acid, succinic acid, acetic acid, sebaceous acid, itaconic acid, tartaric acid, trimellitic acid, fatty dimer acid, or a carboxyl (-C(O)OH) functionalized polyester, wherein the carboxyl (-C(O)OH) functionalized polyester is particularly preferably formed from: divalent to hexavalent carboxylic acids (e.g., maleic acid, succinic acid, acetic acid) The polyester is formed by condensation of sebaceous acid, itaconic acid, tartaric acid, trimellitic acid, and fatty dimer acids with divalent to hexavalent alcohols or epoxides (e.g., ethylene oxide, propylene oxide, butane oxide, and compounds including at least one glycidyloxy group, such as glycidyl, diglycidyl ether, glycerol diglycidyl ether, glycerol triglycidyl ether, and oligoglycerol glycidyl ether, butanediol diglycidyl ether), particularly succinic acid, maleic acid, and tartaric acid, and condensation products of fatty dimer acids and glycerol diglycidyl ether. The polyester is particularly preferably derived from oligomeric hydroxycarboxylic acids, especially oligomeric lactic acid, 12-hydroxystearic acid, hydroxyeicosenoic acid, and ricinoleic acid.

[0473] - Straight-chain, cyclic, or branched, saturated, unsaturated, or aromatic hydrocarbon groups, substituted with OH, ranging from monovalent to octavalent, preferably divalent to octavalent, more preferably divalent to hexavalent, and even more preferably divalent, trivalent, and tetravalent, optionally substituted with OH: derived from esters of halogenated carboxylic acids, preferably chlorocarboxylic acids, having a total of more than five, preferably more than six carbon atoms, such as chloroacetic acid, 3-chloropropionic acid, 4-chlorobutyric acid, or the corresponding bromocarboxylic acid, and OH-functionalized polyesters, wherein the OH-functionalized polyesters are particularly preferably derived from divalent to hexavalent carboxylic acids (e.g., maleic acid, succinic acid, etc.). It is formed by the condensation of acids, fatty acids, sebaceous acids, itaconic acids, tartaric acids, trimellitic acids, and fatty dimer acids with divalent to hexavalent alcohols or epoxides (e.g., ethylene oxide, propylene oxide, butane oxide, and compounds including at least one glycidyloxy group, such as glycidyl, diglycidyl ether, glycerol diglycidyl ether, glycerol triglycidyl ether, and oligoglycerol glycidyl ether, butanediol diglycidyl ether) as outlined above, particularly condensation products of succinic acid, maleic acid, and tartaric acid or fatty dimer acids with glycerol diglycidyl ether.

[0474] In a further preferred embodiment of the invention, compounds of the following formula as defined above are provided:

[0475] R 1 (–F) x (I),

[0476] in

[0477] R 1 Selected from poly(epoxyalkane) groups,

[0478] Preferably, the poly(epoxyalkane) group of general formula (IX) is used:

[0479] -[CH2CH2O] q1 -[CH2CH(CH3)O] r1 -[CH2CH(C2H5)O] s1 -{[CH2CH2] q2 -[CH2CH(CH3)] r2 -[CH2CH(C2H5)] s2}- (IX)

[0480] in

[0481] q1 = 0-49, preferably 0-10, more preferably 1-10, and even more preferably 1-5.

[0482] r1 = 0-32, preferably 0-10, more preferably 1-10, and even more preferably 1-5.

[0483] s1 = 0-24, preferably 0-10, more preferably 1-10, or even more preferably 1-5.

[0484] q2 = 0 or 1,

[0485] r2 = 0 or 1,

[0486] s2 = 0 or 1, and

[0487] ∑(q² + r² + s²) = 1,

[0488] The condition is that the sum of carbon atoms in such poly(epoxyalkane) groups is 2-100, preferably 2-50, more preferably 2-30, even more preferably 2-20, and especially 2-15, or

[0489] R 1 Divalent hydrocarbon groups derived from oligoglycerol and selected from general formula (X):

[0490] -[CH2CH(R 8 CH2O] t1 -[CH2CH(R 8 )CH2)] t2 - (X)

[0491] in

[0492] t1 = 0-32, preferably 0-10, more preferably 1-10, even more preferably 1-5, especially 1 and 2.

[0493] t2 = 1,

[0494] R 8 =OH or -OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7 -OC(O)-R 6 -N + (R 3 ,R 4 ,R 5 ),

[0495] Where m, X, R 3 R 4 R 5 R 6 and R 7 As defined above,

[0496] The condition is that the sum of carbon atoms is 2-100, preferably 2-50, more preferably 2-30, even more preferably 2-20, especially 2-15, or R 1 Selected from

[0497] Divalent hydrocarbon groups of general formulas (XI) and (XII) including at least one ester group:

[0498] -[CH2CH2O] q1 -R 9 -[CH2CH2O] q1 -[CH2CH2] q2 - (XI)

[0499] Where q1 is the same or different and as defined above, and q2 = 1

[0500] -[CH2CH(R 8 CH2O] t1 -R 9 -[CH2CH(R 8 CH2O] t1 -[CH2CH(R 8 )CH2)] t2 - (XII)

[0501] Where t1, t2 and R 8 As defined above, and

[0502] R 9 Selected from -C(O)C(O)O- and -C(O)(CH2) 1-8C(O)O- (e.g., derived from succinic acid, acetic acid, and sebaceous acid), or -C(O)(C6H4)C(O)O- (i.e., derived from phthalic acid and terephthalic acid), -C(O)CH=CHC(O)O-, -C(O)C(=CH2)-CH2C(O)O-, -C(O)CH(OH)CH(OH)C(O)O-,

[0503] The condition is that R 9 The sum of carbon atoms in it is 2-100, preferably 2-50, more preferably 2-30, even more preferably 2-20, and particularly 2-15.

[0504] According to this embodiment, preferably, q2 = 0, and one or both of q1, r1 and s1 are 0, and more preferably...

[0505] q2 = 0, r1 and s1 are 0, or

[0506] q2 = 0, q1 and s1 are 0.

[0507] In a further preferred embodiment of the invention, the compound of general formula (I) is as defined in the above embodiments, and R 1 It contains one or more, for example, 1-5 –O– groups. These –O– groups are preferably ether groups, but can also form ester groups together with carbonyl groups, and preferably the group R. 1 It is replaced by one or more hydroxyl groups.

[0508] In a further preferred embodiment of the invention, compounds of the following formula as defined above are provided:

[0509] R 1 (–F) x (I)

[0510] in

[0511] When bonded to N + group R 1 R 3 R 4 R 5 When one or more of them contain at least one part having general formula (III) or (IV), preferably having general formula (IIIa) or (IVa):

[0512] (–X–C(O)–R 6 ) m –X–C(O)– (III), or

[0513] (–C(O)–X–R 6 ) m –C(O)–X– (IV),

[0514] (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa), or

[0515] (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa)

[0516] Where m = 1 - 20 and X, R 6 and R 7 As defined above,

[0517] The at least one part has a structure of general formula (XIII) or (XIV), preferably general formula (XIIIa) and (XIVa).

[0518] -R 10 (–X–C(O)–R 6 ) m –X–C(O)– (XIII), or

[0519] -R 10 (–C(O)–X–R 6 ) m –C(O)–X– (XIV),

[0520] -R 10 (–X–C(O)–R 6 ) m –X–C(O)–R 7 (XIIIa)

[0521] -R 10 (–C(O)–X–R 6 ) m –C(O)–X–R 7 (XIVa).

[0522] Where R 10 The optionally substituted hydrocarbon group is selected from divalent to octavalent, preferably divalent to decavalent, more preferably divalent to decavalent, particularly divalent, trivalent, tetravalent, pentavalent, hexavalent, heptavalent, octavalent, nonavalent, and decavalent, having up to 200 carbon atoms, preferably 2-200 carbon atoms, more preferably 2-100 carbon atoms, even more preferably 2-50 carbon atoms, particularly 2-20 carbon atoms, and more particularly 2-10 carbon atoms, and may optionally contain one or more groups selected from: –O–, –NH–, –C(O)–, –C(S)–, tertiary amine group. Quaternary ammonium groups And it can be substituted by –OH or halogen groups, wherein the group R 10 It cannot contain a combination of –C(O)- groups and –O- groups, or a combination of –C(O)- groups and –NH- or tertiary amino groups, that form an internal carboxylic ester group or an internal amide group.

[0523] and preferably R 10 It is represented as follows:

[0524] - Divalent groups, particularly -CH2-, -CH2CH2-, and -CH2CH2CH2-, are preferably derived from monochlorocarboxylic acids such as chloroacetic acid, chloropropionic acid, and chlorobutyric acid, or preferably from tertiary amino alcohols such as N,N-dimethylethanolamine and N,N-dimethylpropanolamine.

[0525] - A trivalent group, preferably derived from the partial esters of the monochlorocarboxylic acid, particularly esters of chloroacetic acid and trivalent alcohols (especially glycerol, trimethylolpropane, castor oil (ricinoleic acid triglyceride)), or preferably derived from tertiary amino alcohols such as N,N,N'-trimethylaminoethyl-ethanolamine, or preferably derived from esters of tertiary amino alcohols (especially N,N-dimethylethanolamine, N,N-dimethylpropanolamine) and dihydroxycarboxylic acids (especially 2,2-hydroxymethylpropionic acid).

[0526] -Tetravalent to hexavalent groups, preferably derived from the partial esters of the monochlorocarboxylic acids, particularly esters of chloroacetic acid with tetravalent alcohols (especially erythritol, pentaerythritol, monodiglycerol), pentavalent alcohols (especially xylitol, ditriglycerol), and hexavalent alcohols (especially sorbitol, tritetraglycerol), or preferably esters derived from dendritic oligomers of tertiary amino alcohols (especially N,N-dimethylethanolamine, N,N-dimethylpropanolamine) and dihydroxycarboxylic acid oligomers (especially dendritic oligomers of 2,2-hydroxymethylpropionic acid).

[0527] Heptavalent to octavalent groups, preferably derived from the partial esters of the monochlorocarboxylic acid, particularly esters of chloroacetic acid and heptavalent to octavalent alcohols (especially pentaglycerol to hexadecylglycerol),

[0528] The condition is that R 10 Connect to N via a single key + Partially attached to at least one group having a structure of general formula (III) or (IV), preferably 1, 2, 3, or 4 groups.

[0529] (–X–C(O)–R 6 ) m –X–C(O)– (III), or

[0530] (–C(O)–X–R 6 ) m–C(O)–X– (IV), and more preferably, groups attached to 1, 2, 3, or 4 groups having the general formula (IIIa) or (IVa).

[0531] (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa)

[0532] (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa)

[0533] Where X, m, R 11 R 6 R 7 As defined above.

[0534] According to the above implementation methods, the following is preferred:

[0535] X = O,

[0536] R 6 The group is independently selected from hexene, heptene, octene, nonene, decene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecanylene, octadecylene, nonadecanylene, eicosylene, icosylene, icosylene, tridecylene, and tetradecylene, or hexene, heptene, octene, nonene, decene, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, icosylene, eicosylene, icosylene, icosylene, tridecenyl, icosylene, and tetradecenyl, wherein the group is most preferably bonded to an adjacent C(O) group or O group via a terminal C atom, and if present,

[0537] R 7The group is independently selected from hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, dodecyl, tridecyl, tridecyl, and tetradecyl, optionally substituted with a hydroxyl group, or hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanenyl, eicosenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanenyl, octadecenyl, nonadecanenyl, eicosenyl, dodecenyl, tridecenyl, and tetradecenyl, wherein the group is most preferably bonded to an adjacent C(O) group via a terminal C atom.

[0538] and

[0539] m is 1-10, preferably 1, 2, 3, 4 or 5.

[0540] It is even more preferred when X = 0,

[0541] R 6 Selected from hexadecylene, heptadecanylene, octadecylene, nonadecanylene, eicosylene, hexadecenylene, heptadecanylene, octadecenylene, nonadecanylene, eicosylene, and if present,

[0542] R 7 Selected from hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanenyl, and eicosenyl.

[0543] And m can be 1, 2, 3, 4 or 5.

[0544] According to this implementation, the following is the most preferred condition:

[0545] X = O,

[0546] R 6 Derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or hydroxyeicosenoic acid, and if present,

[0547] R 7 Derived from oleic acid, ricinoleic acid, or stearic acid, and

[0548] m can be 1, 2, 3, 4 or 5.

[0549] In a further preferred embodiment of the invention, a compound of the following formula as defined in the preceding embodiments is provided:

[0550] R 1 (–F) x (I)

[0551] Among them, for the following parts

[0552] -R 10 (–X–C(O)–R 6 ) m –X–C(O)– (XIII) or preferably

[0553] R 10 (–X–C(O)–R 6 ) m –X–C(O)–R 7 (XIIIa)

[0554] And with R 10 When the adjacent X is 0,

[0555] R 10 Derived from

[0556] A mono- or di-(chloroacetic acid) ester of glycerol or castor oil (ricinoleic acid triglyceride), and bonded to a total of one or both moieties (–X–C(O)–R). 6 ) m –X–C(O)–, preferably (-XC(O)-R 6 ) m -OC(O)-R 7 ,

[0557] -or R 10 Derived from

[0558] Esters of tertiary amino alcohols (especially N,N-dimethylethanolamine, N,N-dimethylpropanolamine, N,N,N'-trimethylaminoethyl-ethanolamine) and bonded to a total of one moiety (-XC(O)-R 6 ) m -OC(O)-R 7 Preferably (-XC(O)-R) 6 ) m -OC(O)-R 7 ,

[0559] Or R 10 Esters derived from tertiary amino alcohols (especially N,N-dimethylethanolamine and N,N-dimethylpropanolamine) and dihydroxycarboxylic acids (especially 2,2-hydroxymethylpropionic acid), and bonded to a total of two moieties (–X–C(O)–R). 6 ) m –X–C(O)–, preferably (-XC(O)-R 6 ) m -OC(O)-R 7 ,

[0560] Or R 10 Esters derived from dendritic oligomers of tertiary amino alcohols (especially N,N-dimethylethanolamine and N,N-dimethylpropanolamine) and dihydroxycarboxylic acids (especially dendritic oligomers of 2,2-hydroxymethylpropionic acid), and bonded to a total of more than two, preferably three or four moieties (–X–C(O)–R). 6 ) m –X–C(O)–, preferably (-XC(O)-R 6 ) m -OC(O)-R 7 ,

[0561] and for the following parts

[0562] -R 10 (–X–C(O)–R 6 ) m –X–C(O)– (XIII) or preferably

[0563] -R 10 (–X–C(O)–R 6 ) m –X–C(O)–R 7 (XIIIa)

[0564] In relation to R 10 When the number of adjacent X's is N,

[0565] R 10 Derived from

[0566] tertiary-primary amines, especially N,N-dimethyl-1,3-propanediamine and N-methyl-N'-aminopropyl-piperazine; tertiary-secondary amines, especially N-methylpiperazine; and

[0567] For these two types of parts

[0568] R 6 As defined above, and preferably derived from lactic acid, ricinoleic acid, hydroxyeicosenoic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, 14-hydroxytetradecanoic acid, and most preferably derived from ricinoleic acid or hydroxyeicosenoic acid,

[0569] R 7 As defined above and preferably derived from octadecanoic acid, eicosanoic acid, docosanoic acid, 2-ethylhexanoic acid, 2,2-dimethylpropionic acid, neodecanoic acid, and oleic acid,

[0570] m = 1-20, preferably 1-10, more preferably 1-6, even more preferably 2-6, especially 1, 2, 3, 4, 5, 6, 7, and

[0571] R 6 +R7 The total number of carbon atoms in (∑R) 6 and R 7 The carbon atoms (of which) are 19-300, preferably 25-300, more preferably 35-300, even more preferably 50-300, particularly 35-200, even more particularly 35-150, even more particularly 50-150.

[0572] R 11 Preferably selected from hydrogen or cycloalkylene groups, especially those derived from piperazine rings.

[0573] In a further preferred embodiment of the invention, a compound is provided as defined in the preceding two embodiments:

[0574] R 1 (–F) x (I)

[0575] in

[0576] R 6 As defined above, and preferably derived from lactic acid, ricinoleic acid, hydroxyeicosenoic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, 14-hydroxytetradecanoic acid, and most preferably derived from ricinoleic acid or hydroxyeicosenoic acid,

[0577] R 7 As defined above and preferably derived from octadecanoic acid, eicosanoic acid, docosanoic acid, 2-ethylhexanoic acid, 2,2-dimethylpropionic acid, neodecanoic acid, and oleic acid,

[0578] and for the following parts

[0579] -R 10 (–X–C(O)–R 6 ) m –X–C(O)– (XIII), and

[0580] -R 10 (–C(O)–X–R 6 ) m –C(O)–X– (XIV),

[0581] Preferably for the following parts

[0582] -R 10 (–X–C(O)–R 6 ) m –X–C(O)–R 7 (XIIIa), and

[0583] -R 10 (–C(O)–X–R 6 ) m–C(O)–X–R 7 (XIVa)

[0584] Intra-ester group R 6 And if R exists 7 The sequence (order) is random or blocky, and for blocky sequences, the compound contains a structure of general formula (XV) or (XVI), preferably general formula (XVa) or (XVIa):

[0585] -R 10 -XC(O)-R 6 (–X–C(O)–R 61 ) m1 (–X–C(O)–R 62 ) m2 -X–C(O)– (XV)

[0586] -R 10 -C(O)-XR 6 (–C(O)–X–R 61 ) m1 (–C(O)–X–R 62 ) m2 –C(O)–X– (XVI),

[0587] -R 10 -XC(O)-R 6 (–X–C(O)–R 61 ) m1 (–X–C(O)–R 62 ) m2 -X–C(O)–R 7 (XVa)

[0588] -R 10 -C(O)-XR 6 (–C(O)–X–R 61 ) m1 (–C(O)–X–R 62 ) m2 –C(O)–X–R 7 (XVIa)

[0589] in

[0590] R 61 and R 62 Selected from R 6 ,

[0591] m1 = 0-20, preferably 0-10, more preferably 0-6, even more preferably 1-6, particularly 0, 1, 2, 3, 4, 5, 6.

[0592] m2 = 0-20, preferably 0-10, more preferably 0-6, even more preferably 1-6, particularly 0, 1, 2, 3, 4, 5, 6.

[0593] m = (m1 + m2) + 1,

[0594] m = 1-20, preferably 1-10, more preferably 1-6, even more preferably 1-6, particularly 1, 2, 3, 4, 5, 6, 7, and

[0595] R 6 +R 7 The total number of carbon atoms in (∑R) 6 and R 7 The carbon atoms (of which) are 19-300, preferably 25-300, more preferably 35-300, even more preferably 50-300, particularly 35-200, even more particularly 35-150, even more particularly 50-150.

[0596] The sequences of the structures of general formulas (XV) and (XVI) are preferably selected from...

[0597]

[0598] The sequences of structures of general formulas (XVa) and (XVIa) are preferably selected from...

[0599]

[0600] According to this embodiment, it is particularly preferred when: R 6 R 61 R 62 Combination or R 6 R 61 R 62 and R 7 The combinations are selected based on the specific compounds named in one of the rows of the table above.

[0601] In some

[0602] (–X–C(O)–R 6 ) m –X–C(O)– (III) and

[0603] (–C(O)–X–R 6 ) m –C(O)–X– (IV)

[0604] The introduction of R, which is either monomodal or multimodal in terms of its molecular weight distribution, is described. 6Ester segments are generally within the scope of this invention. In the context of this invention, the term monomodal means that ≥80% of the ester segments have the same molecular weight. The term multimodal means that none of the individual ester segments reach 80% of the total composition.

[0605] In some

[0606] (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa) and

[0607] (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa)

[0608] The introduction of R, which is either monomodal or multimodal in terms of its molecular weight distribution, is described. 6 and R 7 The ester segments are also generally within the scope of this invention.

[0609] In particular, in the following sections

[0610] -R 10 (–X–C(O)–R 6 ) m –X–C(O)– (XIII) and

[0611] -R 10 (–C(O)–X–R 6 ) m –C(O)–X– (XIV),

[0612] Especially in the following sections

[0613] -R 10 (–X–C(O)–R 6 ) m –X–C(O)–R 7 (XIIIa) and

[0614] -R 10 (–C(O)–X–R 6 ) m –C(O)–X–R 7 (XIVa)

[0615] Introducing R, which is either unimodal or multimodal in terms of its molecular weight distribution. 6 And if R exists 7 The ester segments are within the scope of this invention. The terms "unimodal" and "multimodal" have the meanings as defined above.

[0616] According to this embodiment, the following is preferred:

[0617] X = O,

[0618] R 6 The group is independently selected from hexene, heptene, octene, nonene, decene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecanylene, octadecylene, nonadecanylene, eicosylene, icosylene, icosylene, tridecylene, and tetradecylene, or hexene, heptene, octene, nonene, decene, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, icosylene, eicosylene, icosylene, icosylene, tridecenyl, icosylene, and tetradecenyl, wherein the group is most preferably bonded to an adjacent C(O) group or O group via a terminal C atom, and if present,

[0619] R 7 The group is independently selected from hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, dodecyl, tridecyl, and tetradecyl, or hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanenyl, eicosenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanenyl, eicosenyl, dodecenyl, tridecenyl, and tetradecenyl, wherein the group is most preferably bonded to an adjacent C(O) group via a terminal C atom.

[0620] m is 1-10, preferably 1, 2, 3, 4 or 5.

[0621] It is even more preferred when X = 0,

[0622] R 6 Selected from hexadecylene, heptadecanylene, octadecylene, nonadecanylene, eicosylene, hexadecenylene, heptadecanylene, octadecenylene, nonadecanylene, eicosylene, and if present,

[0623] R 7 Selected from hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanenyl, and eicosenyl.

[0624] And m can be 1, 2, 3, 4 or 5.

[0625] According to this implementation, the following is the most preferred condition:

[0626] X = O,

[0627] R 6 Derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or hydroxyeicosenoic acid, and if present,

[0628] R 7 Derived from oleic acid, ricinoleic acid, or stearic acid

[0629] And m can be 1, 2, 3, 4 or 5.

[0630] The introduction of one or more types (mixtures of different structures) of the following portions into compounds according to the invention, which can be mono-, di-, and poly-quaternary ammonium compounds, is also within the scope of the invention:

[0631] (–X–C(O)–R 6 ) m –X–C(O)– (III), and

[0632] (–C(O)–X–R 6 ) m –C(O)–X– (IV).

[0633] Therefore, the introduction of one or more types (mixtures of different structures) of the following into the compounds according to the invention is also within the scope of the invention:

[0634] (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa), and

[0635] (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa),

[0636] The following portions, which are introduced into compounds according to the invention, of one or more types (mixtures of different structures), are also within the scope of the invention:

[0637] -R 10 (–X–C(O)–R 6 ) m –X–C(O)– (XIII), and

[0638] -R 10 (–C(O)–X–R6 ) m –C(O)–X– (XIV),

[0639] And in particular, the introduction of one or more types (mixtures of different structures) of the following into the compounds according to the invention is within the scope of the invention:

[0640] -R 10 (–X–C(O)–R 6 ) m –X–C(O)–R 7 (XIIIa), and

[0641] -R 10 (–C(O)–X–R 6 ) m –C(O)–X–R 7 (XIVa).

[0642] According to the present invention, the following portion contains R 6 ester unit (element)

[0643] (–X–C(O)–R 6 ) m –X–C(O)– (III),

[0644] (–C(O)–X–R 6 ) m –C(O)–X– (IV),

[0645] And especially in the following sections

[0646] (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa), and

[0647] (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa), and

[0648] And even more particularly in the following sections

[0649] -R 10 (–X–C(O)–R 6 ) m –X–C(O)– (XIII),

[0650] -R 10 (–C(O)–X–R 6 ) m–C(O)–X– (XIV)

[0651] -R 10 (–X–C(O)–R 6 ) m –X–C(O)–R 7 (XIIIa), and

[0652] -R 10 (–C(O)–X–R 6 ) m –C(O)–X–R 7 (XIVa),

[0653] For example, in the following sections

[0654] -R 10 -OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-,

[0655] -R 10 -NR 1 -C(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-,

[0656] -R 10 -OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7 ,and

[0657] -R 10 -NR 1 -C(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7 ,

[0658] Containing R 6 and R 7The ester units can be synthesized by esterification of the corresponding carboxylic acids using methods known in the art. In a preferred embodiment, these esterifications can be carried out thermally at 150-350°C, preferably at 180-250°C under reduced pressure (US2011 / 0282084, GB 841554, DE 694943). Alternatively, esterification can be carried out using a catalyst (EP3009494, WO 2012069386, DD 150064, CH 151317, TAIsbell, Grassas y Aceites, 2011, 62(1), 8-20). In another preferred embodiment, an enzyme is used to condense the carboxylic acid (JP 05304966, JP 05211878, JP01016591, A. Bodalo et al., BioChem. Eng. J., 2008, 39(3), 450-456; A. Bodalo et al., BioChem. Eng. J., 2005, 26(2-3), 155-158; Y. Yasuko et al., J. Am. Oil Chem. Soc., 1997, 74(3), 261-267). Typically, the above methods provide multimodal condensates.

[0659] Typically, single-modal condensates can be synthesized by a stepwise esterification sequence based on carboxylic anhydrides (K. Meier, Farbe und Lack, 1951, 57, 437-439; FHH Valentin, J. South African Chem. Inst. 1949, 2, 59-61), or preferably carboxyl chlorides (KD Pathak et al., J. Scientific & Industrial Research, 1955, 14B, 637-639) with the OH groups of hydroxylated carboxylic acids and their derivatives.

[0660] The cyclical repetition of esterification and acyl chloride synthesis provides a generally single-modal ester condensate. Further details will be outlined in the Examples section.

[0661] The following is a schematic representation of the sequence for synthesizing ester condensates based on the stepwise esterification of carboxyl chlorides with the OH groups of hydroxylated carboxylic acids and their derivatives:

[0662]

[0663] Here, the arrows indicate that the product obtained by esterifying the acyl chloride R1-C(O)Cl of a fatty acid with a hydroxy-carboxylic acid HO-R2-C(O)OH and subsequently reacting it with SOCl2 to form an acyl chloride can be subjected to such a reaction sequence again. Therefore, in the next reaction sequence, R1 of the starting material R1-C(O)Cl is “R1-C(O)O-R2” from the previous reaction sequence. Thus, the crosslactone structure can be obtained iteratively, and the number of fatty acid residues included in the final crosslactone moiety is determined by the number of iterative steps in this cyclic process.

[0664] Carboxylic acids without OH groups terminate the chain in ester condensates. Monohydroxycarboxylic acids elongate the chain in ester condensates. Typically, dihydroxy and polyhydroxycarboxylic acids provide branching and dendritic (self-repeating) units within ester condensates.

[0665] In a further preferred embodiment of the invention, compounds of the following formula as defined above are provided.

[0666] R 1 (–F) x (I)

[0667] in

[0668] Low-melting-point and ≥C5 high-melting-point fatty acids are specifically positioned in formulas (III) and (IV) containing R. 6 ester unit

[0669] (–X–C(O)–R 6 ) m –X–C(O)– (III)

[0670] (–C(O)–X–R 6 ) m –C(O)–X– (IV), especially

[0671] Formulas (IIIa) and (IVa) containing R 6 and R 7 ester unit

[0672] (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa), and

[0673] (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa), or

[0674] Formulas (XIII) and (XIV) containing R 6 ester unit

[0675] -R 10 (–X–C(O)–R 6 ) m –X–C(O)– (XIII)

[0676] -R 10 (–C(O)–X–R 6 ) m –C(O)–X– (XIV), especially

[0677] Formulas (XIIIa) and (XIVa) containing R 6 and R 7 ester unit

[0678] -R 10 (–X–C(O)–R 6 ) m –X–C(O)–R 7 (XIIIa)

[0679] -R 10 (–C(O)–X–R 6 ) m –C(O)–X–R 7 (XIVa).

[0680] The following is generally within the scope of this invention: low-melting-point and ≥C5 high-melting-point fatty acids specifically refer to the independent localization of individual ester groups in portions having general formulas (III), (IV), (IIIa), (IVa), (XIII), (XIV), (XIIIa), and (XIVa) present in compounds of general formula (I). For example, this embodiment of the invention is consistent if many portions having general formula (III) exhibit specific localization of low-melting-point and high-melting-point fatty acid scaffolds as described below, while other portions having general formula (III) do not. For different residues R as defined above 1 R 2 R 3 R 4 and R 5 This is especially true for parts of the universe that exist within it.

[0681] Within the framework of this invention, low-melting-point fatty acids with ≥C5 are defined as those with a melting point ≤40°C. Preferred examples include, in particular, oleic acid, hydroxyeicosenoic acid, ricinoleic acid, caprylic acid, decanoic acid, tervamolic acid, and neodecanoic acid.

[0682] Within the framework of this invention, high-melting-point fatty acids with ≥C5 are defined as having a melting point >40°C. Preferred examples include, in particular, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, arachidic acid, benzanoic acid, 10-hydroxyoctadecanoic acid, 12-hydroxyoctadecanoic acid, and 14-hydroxytetradecanoic acid.

[0683] The corresponding melting point can be obtained from the literature (G. Knothe et al., J Am Oil Chem Soc., 2009, 86, 844-856).

[0684] In a further preferred embodiment of the invention, compounds of the following formula as defined above are provided.

[0685] R 1 (–F) x (I)

[0686] in

[0687] Each will form a group R 6 At least one, preferably more than one, more preferably one, two or three low-melting-point fatty acids ≥C5 located in formula (III) or (IV) containing R 6 At one end of the ester unit, at the same time, at least one, preferably more than one, more preferably one, two or three ≥C5 high-melting-point fatty acids are formed at the opposite end of the ester unit of formula (III) or (IV) by one or more groups R. 6 , or such that each forms a group R 6 At least one, preferably more than one, more preferably one, two or three ≥C5 high melting point fatty acids are positioned in formula (III) or (IV) containing R 6 At one end of the ester unit, at the same time, at least one, preferably more than one, more preferably one, two or three ≥C5 low-melting-point fatty acids are formed at one or more groups R at the opposite end of the ester unit of formula (III) or (IV). 6 ,or

[0688] - Each will form a group R 6 At least one, preferably more than one, more preferably one, two or three ≥C5 low-melting-point fatty acids are included in R 7 One or more adjacent groups R 6 In this process, at least one, preferably more than one, more preferably one, two or three ≥C5 high-melting-point fatty acids are formed in formula (IIIa) or (IVa) containing R. 6 and R 7 One or more R groups at opposite ends of the ester unit 6 , or so that each forms R 6At least one, preferably more than one, more preferably one, two or three ≥C5 high melting point fatty acids form with R 7 One or more adjacent groups R 6 Simultaneously, at least one, preferably more than one, more preferably one, two or three ≥C5 low-melting-point fatty acids are formed in formula (IIIa) or (IVa) containing R. 6 and R 7 One or more R groups at opposite ends of the ester unit 6 ,or

[0689] -Each forms a group R 6 At least one, preferably more than one, more preferably one, two or three ≥C5 low-melting-point fatty acids are positioned with the R group. 10 Adjacent to each other, at least one, preferably more than one, more preferably one, two or three ≥C5 high-melting-point fatty acids are formed at one or more groups R at opposite ends of the ester unit of formula (XIII) or (XIV). 6 , or so that each forms R 6 At least one, preferably more than one, more preferably one, two or three ≥C5 high melting point fatty acids form with the group R 10 One or more adjacent groups R 6 Simultaneously, at least one, preferably more than one, more preferably one, two or three ≥C5 low-melting-point fatty acids are formed in formula (XIII) or (XIV) containing R. 6 and R 7 One or more R groups at opposite ends of the ester unit 6 ,or

[0690] -Each forms a group R 6 At least one, preferably more than one, more preferably one, two or three ≥C5 low-melting-point fatty acids are positioned with the R group. 10 Adjacent to each other, at least one, preferably more than one, more preferably one, two or three ≥C5 high melting point fatty acids forming formula (XIIIa) or (XIVa) in the portion thereof, are related to R. 7 One or more adjacent groups R 6 , or so that each forms R 6 At least one, preferably more than one, more preferably one, two or three ≥C5 high melting point fatty acids form with the group R 10 One or more adjacent groups R 6 Simultaneously, at least one, preferably more than one, more preferably one, two or three ≥C5 low-melting-point fatty acids forming formula (XIIIa) or (XIVa) in part with R 7 One or more adjacent groups R 6 .

[0691] As stated above, the specific positioning of high- and low-melting-point fatty acids can be determined by referring to each individual formula containing R in the above-given formulas. 6 The ester portion varies independently.

[0692] The preferred embodiments outlined above allow for the inclusion of R, which exhibits a tendency for localized variation in crystallization, viscosity increase, and phase formation along the entire length of these ester units. 6 and R 6 and R 7 The ester unit is introduced into the part of the following general formula:

[0693] (–X–C(O)–R 6 ) m –X–C(O)– (III)

[0694] (–C(O)–X–R 6 ) m –C(O)–X– (IV),

[0695] (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa), and

[0696] (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa),

[0697] -R 10 (–X–C(O)–R 6 ) m –X–C(O)- (XIII),

[0698] -R 10 (–C(O)–X–R 6 ) m –C(O)–X– (XIV),

[0699] -R 10 (–X–C(O)–R 6 ) m –X–C(O)–R 7 (XIIIa), and

[0700] -R 10 (–C(O)–X–R 6 ) m –C(O)–X–R 7 (XIVa),

[0701] In particular, the following:

[0702] -R 10 -OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-,

[0703] -R 10 -NR 1 -C(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-,

[0704] -R 10 -OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7 ,and

[0705] -R 10 -NR 1 -C(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7 .

[0706] The deliberate combination of the above-mentioned carboxylic acids and synthetic concepts allows for the production of ester condensates with defined molecular weights, molecular weight distributions, carboxylic acid sequences, and properties such as viscosity.

[0707] Typically, group R 10 It can be connected to the following in different ways:

[0708] -R 10 (–X–C(O)–R 6 ) m –X–C(O)–R 7 (XIII),

[0709] -R 10 (–C(O)–X–R 6 ) m –C(O)–X–R 7 (XIV),

[0710] -R 10 (–X–C(O)–R 6 ) m –X–C(O)–R 7 (XIIIa), and

[0711] -R 10(–C(O)–X–R 6 ) m –C(O)–X–R 7 (XIVa),

[0712] In particular, the following:

[0713] -R 10 -OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-, and

[0714] -R 10 -NR 1 -C(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-,

[0715] -R 10 -OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7 ,and

[0716] -R 10 -NR 1 -C(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7

[0717] R 6 and containing R 6 and R 7 The ester unit.

[0718] In a preferred embodiment of the invention, a compound of general formula (I) as defined in the preceding embodiments is provided, wherein R 10 Preferably, R is as follows: 10

[0719] -R 10 (–X–C(O)–R 6 ) m –X–C(O)- (XIII)

[0720] -R 10 (–X–C(O)–R 6 ) m –X–C(O)–R 7 (XIIIa), more preferably R as follows 10

[0721] -R 10 -OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-,

[0722] -R 10 -OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7 ,

[0723] Derived from -OC(O)-R containing two or more parts 6 -(OC(O)-R 6 ) m -OC(O)- castor oil (ricinoleic acid triglyceride) or glycerol mono- or di-(chloroacetic acid) esters or bonded to a total of one or both moieties -OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7 .

[0724] According to this embodiment, the following is preferred:

[0725] X = O,

[0726] R 6 The group is independently selected from hexene, heptene, octene, nonene, decene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecanylene, octadecylene, nonadecanylene, eicosylene, icosylene, icosylene, tridecylene, and tetradecylene, or hexene, heptene, octene, nonene, decene, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, icosylene, eicosylene, icosylene, icosylene, tridecenyl, icosylene, and tetradecenyl, wherein the group is most preferably bonded to an adjacent C(O) group or O group via a terminal C atom, and if present,

[0727] R 7The group is independently selected from hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, dodecyl, tridecyl, and tetradecyl, or hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanenyl, eicosenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanenyl, eicosenyl, dodecenyl, tridecenyl, and tetradecenyl, wherein the group is most preferably bonded to an adjacent C(O) group via a terminal C atom.

[0728] m is 1-10, preferably 1, 2, 3, 4 or 5.

[0729] It is even more preferred when X = 0,

[0730] R 6 Selected from hexadecylene, heptadecanylene, octadecylene, nonadecanylene, eicosylene, hexadecenylene, heptadecanylene, octadecenylene, nonadecanylene, eicosylene, and if present,

[0731] R 7 Selected from hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanenyl, and eicosenyl.

[0732] And m can be 1, 2, 3, 4 or 5.

[0733] According to this implementation, the following is the most preferred condition:

[0734] X = O,

[0735] R 6 Derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or hydroxyeicosenoic acid, and if present,

[0736] R 7 Derived from oleic acid, ricinoleic acid, or stearic acid

[0737] And m can be 1, 2, 3, 4 or 5.

[0738] The prior art describes the esterification of hydroxylated fatty acids or hydroxylated glycerol fatty acid derivatives with chloroacetic acid (R. Oda, Kogyo Kagaku Zasshi, 1933, 36, suppl. Binding 496-497) or chloroacetyl chloride (EP 0283994, A. Baydar et al., Int. J. Cosmet. Sci., 1991, 13(4), 169-190). Further details are summarized in the Examples section.

[0739] In another preferred embodiment of the invention, a compound of general formula (I) as defined above is provided, wherein R 10 Preferably, R is as follows: 10

[0740] -R 10 (–X–C(O)–R 6 ) m –X–C(O)– (XIII), and

[0741] -R 10 (–X–C(O)–R 6 ) m –X–C(O)–R 7 (XIIIa), more preferably R as follows 10

[0742] -R 10 -OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-, and

[0743] -R 10 -OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7 ,

[0744] Esters derived from hydroxylated carboxylic acids and tertiary amino alcohols (especially N,N-dimethylethanolamine, N,N-dimethylpropanolamine, and N,N,N'-trimethylaminoethyl-ethanolamine).

[0745] The prior art (US 2460182) describes the esterification of alcohols containing tertiary amino groups with carboxyl chlorides. Further details are described in the Examples section.

[0746] In another preferred embodiment, R 10 Preferably, R is as follows: 10

[0747] -R10 (–X–C(O)–R 6 ) m –X–C(O)– (XIII), and

[0748] -R 10 (–X–C(O)–R 6 ) m –X–C(O)–R 7 (XIIIa), more preferably R as follows 10

[0749] -R 10 -NR 1 -C(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-, or

[0750] -R 10 -NR 1 -C(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7 ,

[0751] Amides derived from tertiary-primary amines (especially N,N-dimethyl-1,3-propanediamine, N-methyl-N'-aminopropyl-piperazine) and tertiary-secondary amines (especially N-methylpiperazine).

[0752] The prior art describes the synthesis of fatty amides containing tertiary amino groups from fatty acid esters (US 4221733) or free fatty acids (US 3768646). Further details are described in the Examples section.

[0753] In a preferred embodiment of the invention, a compound of general formula (I) is provided, wherein the R portion of the compound of general formula (I) as defined above is... 1 It is formed by the reaction of halogenated carboxylic acids, preferably chloroacetic acid, with OH-functionalized hydrocarbons. The prior art describes the synthesis of chloroacetic acid esters starting from chloroacetic acid or chloroacetyl chloride and OH-functionalized hydrocarbons (R. Oda, Kogyo Kagaku Zasshi, 1933, 36, suppl. Binding 496-497, WO 0210257).

[0754] In another preferred embodiment of the invention, the R of a compound of general formula (I) as defined above 1It is formed by the reaction of an epoxy derivative of a hydrocarbon, preferably a glycidyl ether or glycidyl ester derivative, with a difunctional carboxylic acid. These glycidyl ethers or glycidyl ester derivatives are commercially available or can be synthesized from the corresponding alcohol or carboxylic acid precursors. Preferred commercially available epoxy derivatives are denacol-type (Nagase) or hexion-type modifiers, i.e., derivatives based on 1,4-butanediol, glycerol, oligoglycerol, castor oil, and dimer acids. The synthesis of glycidyl ethers or glycidyl esters is described in the prior art (GB 763559, US3766221, US 5420312, WO 2012041816).

[0755] In another preferred embodiment of the invention, a compound of general formula (I) is provided, wherein R of the compound of general formula (I) as defined above... 1 These esters are formed by reacting esters of halogenated carboxylic acids, preferably chloroacetic acids, with epoxy-functionalized hydrocarbons, or by reacting epoxy-functionalized hydrocarbons with difunctional carboxylic acids. The synthesis of this type of ester is described in US 2018 / 0016397.

[0756] Typically, the counterion A of the ammonium anion of compounds of general formula (I) as defined above is... - The anions are selected from monovalent to trivalent inorganic anions and monovalent to 30,000-valent, preferably monovalent to 1,000-valent organic anions, and are preferably selected from halogens such as chloride, bromide, iodide, sulfate, phosphate, phosphonate, sulfonate, methylsulfate, and carboxyl groups such as acetate, propionate, lactate, octanoate, 2-ethylhexanoate, dodecanoate, hexadecanoate, octadecanoate, oleate, ricinoleate, 12-hydroxy-octadecanoate, succinate, maleate, tartrate, and polyether carboxyl groups.

[0757] The following types of polymeric fatty acid carboxyl groups

[0758] R 1 [(-C(O)-XR 6 ) m -C(O)-XR 7 ] x ,or

[0759] R 1 [(XC(O)-R 6 ) m -XC(O)-R 7 ] x , where R 1 Or at least one R 7 Or R 1 and at least one R 7 Both have one or more carboxylate groups.

[0760] Preferably, where X = 0,

[0761] in particular

[0762] The following types of linear polymeric fatty acid carboxyl groups

[0763] - OC(O)-R 6 (-XC(O)-R 6 ) m-1 -XC(O)-R 7 Preferably

[0764] - OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7 ,

[0765] Branched linear polymeric fatty acid carboxyl groups,

[0766] That is, it is derived from branched polyfatty acid structures, particularly from branched linear polymeric fatty acid carboxyl groups derived from polyfunctional carboxylic acids (especially dicarboxylic acid succinic acid and maleic acid) and esters of castor oil or Resclere oil, such as...

[0767]

[0768] One of them

[0769]

[0770] And the remaining two

[0771]

[0772] Dendritic polymer type fatty acid carboxyl group,

[0773] That is, it is derived from the dendritic polyfatty acid structure.

[0774] Or the following types of polymeric fatty acid carboxyl groups

[0775] XR 6 (–C(O)–X–R 6 ) m-1 –C(O)–X–R 7 or

[0776] R 6 (–C(O)–X–R 6 ) m-1 –C(O)–X–R7 ,

[0777] In the latter two types, R 7 The group has at least one anionic carboxylate group.

[0778] Or the following types of polymeric fatty acid carboxyl groups

[0779] R 1 [(-C(O)-X-R6) m -C(O)O - ] x ,For example

[0780] Among them, X and R 1 R 6 R 7 m and x are as defined above, and

[0781] The counter ion A of this group - Preferably, the valence is monovalent to fiftievalent, more preferably monovalent to decavalent, even more preferably monovalent to pentavalent, and most preferably pentavalent, tetravalent, trivalent, divalent, or monovalent anions.

[0782] Alternatively, the counter anion may be selected from carboxylate anions based on poly(acrylic acid) homopolymers and copolymers, and poly(itaconic acid) homopolymers and copolymers.

[0783] The anion of this group is preferably divalent to 30,000 valence, more preferably divalent to 1,000 valence, even more preferably decavalent to 1,000 valence, even more preferably 50 valence to 1,000 valence, and most preferably 100 valence to 1,000 valence anion.

[0784] Preferably, the carboxyl group of polymeric fatty acids is selected from single-chain molecules that are not esterified OH substituents.

[0785] - OC(O)-R 6 (–X–C(O)–R 6 ) m-1 –X–C(O)–R 7 ,

[0786] or

[0787] Preferably, the fatty acid carboxyl groups are selected from the following types as defined above.

[0788] R 1 [(-C(O)-X-R6) m -C(O)O - ] x

[0789] It is a carboxylate group, particularly derived from 2,2'-di-hydroxymethylpropionic acid, containing branched or dendritic (self-repeating) motifs.

[0790] The synthesis of the dendritic structure of 2,2'-di-hydroxymethylpropionic acid is described in US 2016 / 0102179.

[0791] In a further preferred embodiment of the invention, the counterion A of the compound of the invention according to general formula (I) as defined above - The anions are monovalent to trivalent inorganic anions and monovalent to 30,000-valent, preferably monovalent to 1,000-valent organic anions, selected from: halide anions such as chloride, bromide, iodide, sulfate, phosphate, phosphonate, sulfonate, methylsulfate, carboxylate anions such as acetate, propionate, lactate, octanoate, 2-ethylhexanoate, dodecanoate, hexadecanoate, octadecanoate, oleate, ricinoleate, 12-hydroxy-octadecanoate, succinate, maleate, tartrate, polyether carboxylate.

[0792] The following types of polymeric fatty acid carboxyl groups

[0793] R 1 [(-C(O)-XR 6 ) m -C(O)-XR 7 ] x ,or

[0794] R 1 [(XC(O)-R 6 ) m -XC(O)-R 7 ] x , where R 1 Or at least one R 7 Or R 1 and at least one R 7 Both have one or more carboxylate groups.

[0795] Preferably, where X = 0,

[0796] in particular

[0797] The following types of linear polymeric fatty acid carboxyl groups

[0798] - OC(O)-R 6 (-XC(O)-R 6 ) m-1 -XC(O)-R 7 Preferably

[0799] - OC(O)-R6 -(OC(O)-R 6 ) m -OC(O)-R 7 ,

[0800] Branched linear polymeric fatty acid carboxyl groups,

[0801] That is, it is derived from branched polyfatty acid structures, particularly from branched linear polymeric fatty acid carboxyl groups derived from polyfunctional carboxylic acids (especially dicarboxylic acid succinic acid and maleic acid) and esters of castor oil or Resclere oil, such as...

[0802]

[0803] One of them

[0804]

[0805] And the remaining two

[0806]

[0807] Dendritic polymer type fatty acid carboxyl group,

[0808] That is, it is derived from the dendritic polyfatty acid structure.

[0809] Or the following types of polymeric fatty acid carboxyl groups

[0810] XR 6 (–C(O)–X–R 6 ) m-1 –C(O)–X–R 7 or

[0811] R 6 (–C(O)–X–R 6 ) m-1 –C(O)–X–R 7 ,

[0812] In the latter two types, R 7 The group has at least one anionic carboxylate group.

[0813] Or the following types of polymeric fatty acid carboxyl groups

[0814] R 1 [(-C(O)-X-R6) m -C(O)O - ] x ,For example

[0815] Among them, X and R 1R 6 R 7 m and x are as defined above, and the counter ion A of this group is... - Preferably, the valence is monovalent to fiftievalent, more preferably monovalent to decavalent, even more preferably monovalent to pentavalent, and most preferably pentavalent, tetravalent, trivalent, divalent, or monovalent anions.

[0816] Alternatively, it may be derived from poly(acrylic acid) homopolymers and copolymers, poly(itaconic acid) homopolymers and copolymers, wherein the anion of the group is preferably divalent to 30,000 valence, more preferably divalent to 1,000 valence, even more preferably decavalent to 1,000 valence, even more preferably fiftievalent to 1,000 valence, and most preferably 100 valence to 1,000 valence anion.

[0817] Preferably, the following type of polymeric fatty acid carboxyl group

[0818] - OC(O)-R 6 (–X–C(O)–R 6 ) m-1 –X–C(O)–R 7

[0819] It is a single-chain molecule without esterified OH substituents, or

[0820] Preferably, polymeric fatty acid carboxyl groups of the type defined above are preferred.

[0821] R 1 [(-C(O)-X-R6) m -C(O)O - ] x

[0822] It is a carboxylate group, particularly derived from 2,2'-di-hydroxymethylpropionic acid, containing branched or dendritic (self-repeating) motifs.

[0823] Desired counterions can be introduced into quaternized materials during quaternization or via anion exchange. In this regard, inorganic counterions such as chlorine or bromine can be exchanged with organic counterions such as fatty acid carboxylates or polymeric fatty acid carboxylates by adding alkali metal salts, preferably sodium and potassium salts, of fatty acids or polymeric fatty acids to materials containing initially inorganic counterions, thereby producing the target material and alkali metal halides, particularly NaCl, NaBr, KCl, and KBr.

[0824] In a preferred embodiment of the invention, X = 0 in formula (III) and / or (IV), and preferably, the compound according to the invention does not contain any amide groups.

[0825] Compared to ester groups, amide bonds are generally more stable to hydrolysis; however, they also impart structural rigidity. According to this embodiment, therefore, in all structures of formula (III) and / or (IV) present in the said compounds, group X represents an oxygen atom, and preferably, the compounds do not contain any amide groups at all.

[0826] In another preferred embodiment, in the compounds according to the invention, the group R present in the cationic structures of general formulas (I) and (II) 1 R 2 R 3 R 4 R 5 At least one contains at least one part having the following formula

[0827] R 1* [(-OC(O)-R 6 ) m –O–C(O)-]2,

[0828] Where R 1* It is a divalent C1-C100 hydrocarbon group, preferably a C1-C12 alkylene group, most preferably methylene, ethylene, 1,3-propylene, 1,4-butylene, 1,6-hexylene, 1,2-propylene, or 1,3-butylene, where m is independently selected from 1-12, and

[0829] R 6 As defined above.

[0830] Among them, the following part

[0831] R 1* [(-OC(O)-R 6 ) m –O–C(O)-]2,

[0832] Preferably formed from alkylene glycols, more preferably from α,o-alkylene glycols such as 1,2-ethylene glycol, 1,3-propanediol, 1,4-butanediol and 1,6-hexanediol, via sequential or block ester chain formation.

[0833] Whether the carboxylic acid, to be replaced by a single hydroxyl group, is added iteratively, or a cross-lactone chain with a carboxylic acid group is reacted with such a diol, the use of an excess of carboxylic acid reactant leads to the formation of a product in which the diol is esterified primarily at both ends in the same manner, thus obtaining a symmetrical structure as shown in the following formula.

[0834] R 1* [(-OC(O)-R 6 ) m –O–C(O)-]2.

[0835] Group R 1* The structure of this structure usually corresponds directly to the alkylene glycol used as the starting material.

[0836] According to the present invention, R 1* It is a divalent C2-C100 hydrocarbon group, which includes all types of linear, branched and cyclic aliphatic and aromatic divalent hydrocarbon groups, such as alkylene, alkenylene, ynylene, and aromatic structures such as phenylene.

[0837] Since C1-C12 alkylene glycols are preferred starting materials, therefore R 1* Preferably, it is a C1-12 alkylene group, more preferably methylene, ethylene, n-propylene, n-butylene, n-pentylene, n-hexylene, or even more preferably methylene, ethylene, n-propylene, n-butylene, or n-hexylene groups.

[0838] Although m is chosen independently according to this embodiment, it is preferred that the two m in the following general structure are the same R. 1* [(-OC(O)-R 6 ) m –O–C(O)-]2,

[0839] Because the aforementioned parts are typically symmetrical.

[0840] Further preferably, m is independently selected from 1-6, more preferably 1-4, even more preferably the two m are the same and selected from 1-6, and most preferably the two m are the same and selected from 1-4.

[0841] According to this implementation method, R 6 As defined above, but preferably R 6 The group is selected from linear alkylene groups and linear alkenyl groups, particularly from linear C6-C24 alkylene groups such as hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecanylene, octadecylene, nonadecanylene, eicosylene, dodecylene, tridecylene, and tetradecylene, or linear C6-C24 alkenyl groups. Groups such as hexeneyl, heptenyl, octeneyl, noneneyl, deceneyl, undeceneyl, dodeceneyl, trideceneyl, tetradeceneyl, pentadeceneyl, hexadeceneyl, heptadeceneyl, heptadeceneyl, octadeceneyl, nonadeceneyl, icoseneyl, icoseneyl, icoseneyl, icoseneyl, icoseneyl, and tetradeceneyl are most preferably bonded to an adjacent C(O) group via a terminal C atom.

[0842] More preferably, R 6Derived from C7-C25 fatty acids having a hydroxyl group as a substituent, or even more preferably R 6 It is derived from ricinoleic acid, hydroxyeicosenoic acid, 10-hydroxyoctadecanoic acid, 12-hydroxyoctadecanoic acid, 14-hydroxytetradecanoic acid, 10-hydroxystearic acid, and 12-hydroxystearic acid.

[0843] The most preferred option R 6 It is derived from ricinoleic acid.

[0844] In this and any other implementation as described herein, it is generally preferred that all R values ​​of the following general formulas are included. 6 The functional groups are the same:

[0845] R 1* [(-OC(O)-R 6 ) m –O–C(O)-]2.

[0846] In a further preferred embodiment, in the compounds according to the invention, the group R present in the cationic structures of general formulas (I) and (II) 1 R 2 R 3 R 4 R 5 At least one contains at least one part having the following formula:

[0847] R 1* [(-OC(O)-R 6 ) m –O–C(O)-]2,

[0848] Where R 1* Selected from methylene, ethylene, 1,3-propylene, 1,4-butylene, 1,6-hexylene, 1,2-propylene, and 3-butylene.

[0849] R 6 Derived from C8-C24 monocarboxyl-monohydroxycarboxylic acids, particularly from ricinoleic acid, 12-hydroxystearic acid, hydroxyeicosenoic acid, and 11-hydroxy-undecanoic acid, and m is independently selected from 1-6.

[0850] According to this implementation, preferably, all R 6 It is derived from the same carboxylic acid, and the two m's in this structure are identical.

[0851] In one or even more preferred embodiment, in the compounds according to the invention, the group R present in the cationic structures of general formulas (I) and (II) 1 R 2 R 3 R4 R 5 At least one contains at least one part having the following formula

[0852] R 1* [(-OC(O)-R 6 ) m –O–C(O)-]2,

[0853] It is represented by one of the following structural formulas:

[0854] -C(O)-O-(mono- or oligomeric C8-C24 hydroxy fatty acids)-C(O)-O-(C2-C10 hydrocarbons)-OC(O)-(mono- or oligomeric C8-C24 hydroxy fatty acids)-OC(O)-

[0855] in

[0856] -C2-C10 hydrocarbons are C2-C10 alkylene groups, particularly derived from ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, 1,2-propanediol, and 1,3-butanediol.

[0857] - Mono- or oligomeric C8-C24 hydroxy fatty acids have the following groups: they are derived from hydroxyl-substituted C8-C24 carboxylic acid monomers or oligomers of C8-C24 carboxylic acid monomers with up to 20 hydroxyl-substituted monomers formed by esterification, particularly derived from mono- or oligomeric ricinoleic acid, wherein the degree of oligomerization is 2-20, preferably 2-10, more preferably 2-6, and even more preferably 2-4.

[0858] Such compounds are exemplified by the following structural formulas:

[0859]

[0860] Where R:

[0861]

[0862]

[0863] Where R:

[0864]

[0865] In a further preferred embodiment, in the compounds according to the invention, the group R present in the cationic structures of general formulas (I) and (II) 1 R 2 R 3 R 4 R 5 At least one contains at least one part having the following formula

[0866] R 1* [(-OC(O)-R 6 ) m –O–C(O)-R 7 *-]2,

[0867] in

[0868] R 1* R 6 , and m are as defined above,

[0869] And R 7* It is a C1-C12 alkylene group, preferably a methylene, ethylene, propylene, or butylene group.

[0870] In this embodiment, the lactone chain of the portion shown above is bonded to an alkylene group, typically after forming the lactone chain structure included in the portion of the following general formula.

[0871] R 1* [(-OC(O)-R 6 ) m –O–C(O)-R 7 *-]2,

[0872] The terminal hydroxyl group of the chain structure is reacted with a carboxylic acid or carboxyl chloride, particularly a haloalkyl carboxyl chloride, having a functionalized alkyl chain. Through this reaction, the group R... 7* The precursor is attached to this structure, and upon further functionalization, a portion of the following general structure is obtained:

[0873] R 1* [(-OC(O)-R 6 ) m –O–C(O)-R 7 *-]2.

[0874] According to this implementation method, R 7* It is a C1-C12 alkylene group, preferably a methylene, ethylene, propylene, or butylene group, with a methylene group being the most preferred.

[0875] For example, R as a methylene group 7* This can be achieved by esterifying the terminal hydroxyl group of the lactone chain with chloroacetyl chloride, and then functionalizing it, for example by using a chlorine group as a leaving group (e.g., in the quaternization reaction of tertiary amines).

[0876] In a further preferred embodiment, in the compounds according to the invention, the group R present in the cationic structures of general formulas (I) and (II) 1 R 2 R 3 R 4R 5 At least one contains at least one part having the following formula

[0877] R 1* [(-OC(O)-R 6 ) m –O–C(O)-R 7 *-]2,

[0878] in

[0879] R 1* Selected from methylene, ethylene, 1,3-propylene, 1,4-butylene, and 1,6-hexylene.

[0880] R 6 Derived from C8-C24 monocarboxylic acids, particularly ricinoleic acid, 12-hydroxystearic acid, hydroxyeicosenoic acid, and 11-hydroxyundecanoic acid.

[0881] m is independently selected from 1-6.

[0882] And R 7* Selected from methylene and ethylene.

[0883] In one or even more preferred embodiment, in the compounds according to the invention, the group R present in the cationic structures of general formulas (I) and (II) 1 R 2 R 3 R 4 R 5 At least one contains at least one part having the following formula

[0884] R 1* [(-OC(O)-R 6 ) m –O–C(O)-R 7 *-]2

[0885] It is represented by one of the following structural formulas:

[0886] i)-CH2-C(O)-O-(mono- or oligomeric C8-C24 hydroxy fatty acids)-C(O)-O-(C2-C10 hydrocarbons)-OC(O)-(mono- or oligomeric C8-C24 hydroxy fatty acids)-OC(O)-CH2-

[0887] or

[0888] ii)-CH2CH2-C(O)-O-(mono- or oligomeric C8-C24 hydroxy fatty acids)-C(O)-O-(C2-C10 hydrocarbons)-OC(O)-(mono- or oligomeric C8-C24 hydroxy fatty acids)-OC(O)-CH2CH2-,

[0889] in

[0890] -C2-C10 hydrocarbons are C2-C10 alkylene groups, particularly derived from ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,6-hexanediol, 1,2-propanediol, and 1,3-butanediol.

[0891] - Mono- or oligomeric C8-C24 hydroxy fatty acids have the following groups: oligomers derived from hydroxyl-substituted C8-C24 carboxylic acid monomers or C8-C24 carboxylic acid monomers with up to 20 hydroxyl-substituted oligomers formed by esterification, particularly derived from mono- or oligomeric ricinoleic acid, wherein the degree of oligomerization is 2-20, preferably 2-10, more preferably 2-6, and even more preferably 2-4.

[0892] Such compounds are exemplified by the following structural formulas:

[0893]

[0894] Where R:

[0895]

[0896]

[0897] Where R:

[0898]

[0899] In a further preferred embodiment, in the compound according to the invention, at least one portion having the following general formula

[0900] R 1* [(-OC(O)-R 6 ) m –O–C(O)-R 7 *-]2

[0901] R at one or both ends 7* The group is bonded to a quaternary N atom.

[0902] Therefore, according to this embodiment, the compound according to the invention contains at least one part having the following general formula:

[0903] R 1* [(-OC(O)-R 6 ) m –O–C(O)-R 7 *-N + ]2,

[0904] Two of the ends R 7* All groups are bonded to the quaternary N atom.

[0905] and / or at least one part having the following general formula

[0906] N + -R 7* -C(O)-O-(R 6 -C(O)-O) m -R1*- * (-OC(O)-R 6 ) m –O–C(O)-R 7 *-,

[0907] One of the terminal R 7* The group is bonded to the quaternary N atom.

[0908] More preferably, each of the one or two quaternary N atoms has two groups independently selected from methyl, ethyl, propyl, and butyl groups.

[0909] More preferably, each of the one or two quaternary N atoms has two methyl substituents, and even more preferably, the fourth substituent is an alkylamino group or an alkyl group substituted with an ammonium group, and most preferably the fourth substituent is selected from ethylene dimethylammonium group, propylene dimethylammonium group, butyl dimethylammonium group or hexyl dimethylammonium group.

[0910] Preferably, these groups are derived from N,N,N',N'-tetramethyl-1,2-ethylenediamine, N,N,N',N'-tetramethyl-1,4-butylenediamine, and N,N,N',N'-tetramethyl-1,6-hexylenediamine. Alternatively, quaternary ammonium groups having a methyl group may be derived from N,N'-dimethylpiperazine.

[0911] In another preferred embodiment of the invention, at least one part having the following general formula

[0912] R 1* [(-OC(O)-R 6 ) m –O–C(O)-R 7 *-]2

[0913] R at one or both ends 7* The group is bonded to a quaternary N atom, and the compound is a diquaternary ammonium or quaternary ammonium compound.

[0914] Preferably, the two ends R 7* All groups are bonded to quaternary N atoms, more preferably the two terminal R atoms. 7* Each group is bonded to a quaternary N atom having three alkyl substituents, each having 1-12 carbon atoms, or to a group of the formula -N+ (CH3)2-ALK-N + (CH3)3 represents a quaternary N atom, wherein ALK is a divalent alkylene group having 1-12 carbon atoms, preferably a linear alkylene group.

[0915] According to this embodiment, preferably, if the two ends R 7* The groups are all bonded to a quaternary N atom having three alkyl substituents, each having 1-12 carbon atoms. Preferably, the alkyl substituents are selected from methyl, ethyl, propyl and butyl groups, and most preferably all three substituents are methyl groups.

[0916] If the two ends R 7* All groups are bonded to the -N group as defined above. + (CH3)2-ALK-N + The quaternary N atom represented by (CH3)3 is preferably a methylene group, an ethylene group, a n-propyl group, a n-butylene group, or a n-hexylene group.

[0917] In a further preferred embodiment, the compound according to the invention comprises at least two parts having the following general formula.

[0918] R 1* [(-OC(O)-R 6 ) m –O–C(O)-R 7 *-]2,

[0919] The portions are linked to each other via di-quaternary ammonium alkylene groups with the following general structure:

[0920] -N + (CH3)2-ALK-N + (CH3)2-,

[0921] ALK is a divalent alkylene group having 1-12 carbon atoms, preferably a linear alkylene group.

[0922] Preferably, the compound comprises more than four, more preferably more than six, and even more preferably more than eight portions having the following formula:

[0923] R 1* [(-OC(O)-R 6 ) m –O–C(O)-R 7 *-]2, which is linked via a diammonium alkylene group.

[0924] More preferably, the ALK group is independently selected from ethylene, n-propylene, n-butylene, or n-hexylene, and more preferably, all ALK groups are alkylene groups of the same type.

[0925] In another preferred embodiment of the compound according to the invention, the group R present in the cationic structure of general formulas (I) and (II) 1 R 2 R 3 R 4 R 5 At least one contains at least one part having the following general formula: -([-O–C(O)-R 6 (–O–C(O)–R 6 ) l –O–C(O)–LC(O)-O-(R 6 -C(O)-O) l -R 6 -C(O)O])-

[0926] Where R 6 As defined above,

[0927] l is an integer independently selected from 0-20, more preferably 1-12, or even more preferably 2-10, and

[0928] L is a divalent hydrocarbon group, which may have 1-30 carbon atoms and may optionally contain one or more groups selected from the following: –O–, -S–, –NH–, –C(O)–, –C(S)–, and tertiary amino groups.

[0929] Preferably, L is a divalent alkylene or alkenylene group having 1-30 carbon atoms.

[0930] More preferably, L is selected from methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, vinylene, propenylene, butenylene, pentenylene, hexenylene, heptenylene, octylene, and nonenylene.

[0931] The most preferred element L is selected from methylene, ethylene, vinylene, or buteneyl.

[0932] According to this implementation method, R 6 Preferably, it is independently derived from C8-C24 monocarboxylic acid, particularly from ricinoleic acid, 12-hydroxystearic acid, hydroxyeicosenoic acid, and 11-hydroxyundecanoic acid.

[0933] In a preferred embodiment of the compound according to the invention

[0934] The group R present in the cationic structures of general formulas (I) and (II) 1 R 2 R 3 R 4 R 5 At least one contains at least one part having the following general formula: -([-O–C(O)-R 6 (–O–C(O)–R 6 ) l –O–C(O)–LC(O)-O-(R 6 -C(O)-O) l -R 6 -C(O)O])-,

[0935] Where L and l are as defined above.

[0936] And R 6 Independently derived from C8-C24 monocarboxyl-monohydroxycarboxylic acids, preferably derived from ricinoleic acid, 12-hydroxystearic acid, hydroxyeicosenoic acid, 11-hydroxy-undecanoic acid, and most preferably R 6 It is derived from ricinoleic acid.

[0937] More preferably, L is selected from methylene or ethylene, -CH=CH- and -C(=CH2)-CH2-, l is independently selected from integers in the range of 0-6, and R 6 It is derived from ricinoleic acid.

[0938] In a preferred embodiment of the compounds according to the invention, the group R present in the cationic structures of general formulas (I) and (II) 1 R 2 R 3 R 4 R 5 At least one contains at least one part having the following general formula: -([-O–C(O)-R 6 (–O–C(O)–R 6 ) l –O–C(O)–LC(O)-O-(R 6 -C(O)-O) l -R 6 -C(O)O])-,

[0939] Where L is selected from methylene, ethylene, and vinylene.

[0940] R 6 Derived from ricinoleic acid, and

[0941] l is independently selected from 0, 1, 2 and 3, and the sum of l is in the range of 0-4.

[0942] Preferably, L is an ethylene group, and R 6 It is derived from ricinoleic acid, and l is independently selected from 0 or 1.

[0943] In a preferred embodiment of the compounds according to the invention, the group R present in the cationic structures of general formulas (I) and (II) 1 R 2 R 3 R 4 R 5 At least one contains at least one part having the following general formula: -([-O–C(O)-R 6 (–O–C(O)–R 6 ) l –O–C(O)–LC(O)-O-(R 6 -C(O)-O) l -R 6 -C(O)O])-,

[0944] It is represented by the following structure:

[0945] -OC(O)-(mono- or oligomeric C8-C24 hydroxy fatty acids)-OC(O)-(C1-C12 hydrocarbons)-C(O)-O-(mono- or oligomeric C8-C24 hydroxy fatty acids)-C(O)-O-

[0946] in

[0947] -C1-C12 hydrocarbons are C1-C12 hydrocarbon-like groups, preferably C2-C10 hydrocarbon-like groups, and

[0948] - Mono- or oligomeric C8-C24 hydroxy fatty acids with the following groups: oligomers derived from hydroxyl-substituted C8-C24 carboxylic acid monomers or formed by esterification of up to 20 hydroxyl-substituted C8-C24 carboxylic acid monomers, wherein the degree of oligomerization is 2-20, preferably 2-10, more preferably 2-6, and even more preferably 2-4.

[0949] The C1-C12 hydrocarbon groups are preferably derived from succinic acid, maleic acid, itaconic acid, acetic acid, sebaceous acid, or dodecanoic acid.

[0950] The mono- or oligomeric C8-C24 hydroxy fatty acid groups are preferably derived from mono- or oligomeric ricinoleic acid, wherein the degree of oligomerization is 2-20, preferably 2-10, more preferably 2-6, or even more preferably 2-4.

[0951] Compounds with this structure are exemplified by the following:

[0952]

[0953] Where R:

[0954]

[0955]

[0956] In a preferred embodiment of the compounds according to the invention, the group R present in the cationic structures of general formulas (I) and (II) 1 R 2 R 3 R 4 R 5 At least one contains at least one part having the following general formula: -([-O–C(O)-R 6 (–O–C(O)–R 6 ) l –O–C(O)–LC(O)-O-(R 6 -C(O)-O) l -R 6 -C(O)O])-R 12 ,

[0957] Among them, L, l, R 6 As defined above,

[0958] And R 12 It is a C1-C12 linear or branched alkylene group, which may contain up to 4 -O- groups and up to 4 tertiary amino groups, and is bonded to the -O- group of an ester group at one end and to a quaternary N atom at the other end.

[0959] Preferably R 12 Derived from tertiary amino alcohols, especially from amino alcohols having the following structure:

[0960]

[0961] Preferably, L, l, and R 6 As defined above, and R 12 Selected from -CH2CH2- and -CH2CH2CH2-.

[0962] More preferably, l is independently selected from the range of 0-6, preferably 1-6, and more preferably 2-6.

[0963] R 6 Preferably derived from ricinoleic acid, and

[0964] R 12 Preferably selected from -CH2CH2- and –CH2CH2CH2-.

[0965] The present invention also relates to a process for synthesizing compounds of general formula (I) as defined by all preceding embodiments of the invention.

[0966] R 1 (–F) x (I), where

[0967] The alkyl halide is reacted with a tertiary amine, the tertiary amine containing at least one of the following moieties.

[0968] (–X–C(O)–R 6 ) m –X–C(O)– (III), or

[0969] (–C(O)–X–R 6 ) m –C(O)–X– (IV), preferably having at least one of the following portions

[0970] (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa), or

[0971] (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa),

[0972] or

[0973] The reaction is carried out with a tertiary amine, wherein the ester of a halogenated carboxylic acid, preferably chloroacetic acid, and an alcohol or epoxide as defined above, contains at least one of the following moieties:

[0974] (–X–C(O)–R 6 ) m –X–C(O)– (III), or

[0975] (–C(O)–X–R 6 ) m –C(O)–X– (IV), preferably having at least one of the following portions

[0976] (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa), or

[0977] (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa),

[0978] or

[0979] The epoxy-functionalized ethers and esters, preferably glycidyl ethers and esters, of alcohols or carboxylic acids as defined above, are reacted with tertiary amines in the presence of an acid, wherein the tertiary amine contains at least one of the following moieties:

[0980] (–X–C(O)–R 6 ) m –X–C(O)– (III), or

[0981] (–C(O)–X–R 6 ) m –C(O)–X– (IV), preferably having at least one of the following portions

[0982] (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa), or

[0983] (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa),

[0984] or

[0985] Reacting a hydrocarbon containing a tertiary amino group with an ester of a halogenated carboxylic acid as defined above, wherein the ester contains at least one of the following moieties:

[0986] (–X–C(O)–R 6 ) m –X–C(O)– (III), or

[0987] (–C(O)–X–R 6 ) m –C(O)–X– (IV), preferably having at least one portion

[0988] (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa), or

[0989] (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa),

[0990] or

[0991] A hydrocarbon containing a tertiary amino group reacts with an epoxy-functionalized ether and ester as defined above in the presence of an acid, wherein the epoxy-functionalized ether and ester contain at least one of the following moieties.

[0992] (–X–C(O)–R 6 ) m –X–C(O)– (III), or

[0993] (–C(O)–X–R 6 ) m –C(O)–X– (IV), preferably having at least one portion

[0994] (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa), or

[0995] (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa),

[0996] Among them, X and R 6 R 7 m and x are as defined above.

[0997] According to this embodiment, the following is preferred:

[0998] X = O,

[0999] R 6 The group is independently selected from hexene, heptene, octene, nonene, decene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecanylene, octadecylene, nonadecanylene, eicosylene, icosylene, icosylene, tridecylene, and tetradecylene, or hexene, heptene, octene, nonene, decene, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, icosylene, eicosylene, icosylene, icosylene, tridecenyl, icosylene, and tetradecenyl, wherein the group is most preferably bonded to an adjacent C(O) group or O group via a terminal C atom, and if present,

[1000] R 7The group is independently selected from hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, dodecyl, tridecyl, and tetradecyl, or hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanenyl, eicosenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanenyl, eicosenyl, dodecenyl, tridecenyl, and tetradecenyl, wherein the group is most preferably bonded to an adjacent C(O) group via a terminal C atom.

[1001] m is 1-10, preferably 1, 2, 3, 4 or 5.

[1002] It is even more preferred when X = 0,

[1003] R 6 Selected from hexadecylene, heptadecanylene, octadecylene, nonadecanylene, eicosylene, hexadecenylene, heptadecanylene, octadecenylene, nonadecanylene, eicosylene, and if present,

[1004] R 7 Selected from hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanenyl, and eicosenyl.

[1005] And m can be 1, 2, 3, 4 or 5.

[1006] According to this implementation, the following is the most preferred condition:

[1007] X = O,

[1008] R 6 Derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or hydroxyeicosenoic acid, and if present,

[1009] R 7 Derived from oleic acid, ricinoleic acid, or stearic acid

[1010] And m can be 1, 2, 3, 4 or 5.

[1011] In a preferred embodiment of the invention, a process for synthesizing compounds of general formula (I) is provided.

[1012] R 1 (–F) x (I)

[1013] Where R 1By quaternizing nitrogen atoms N + Connect to R 3 R 4 , and R 5 And R 1 (-F) x Contains at least one part having general formula (III) or general formula (IV)

[1014] (–X–C(O)–R 6 ) m –X–C(O)– (III),

[1015] (–C(O)–X–R 6 ) m –C(O)–X– (IV), preferably

[1016] Having at least one part of general formula (IIIa) or general formula (IVa)

[1017] (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa),

[1018] (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa),

[1019] in

[1020] The alkyl halide is reacted with a tertiary amine, the tertiary amine containing at least one of the following moieties.

[1021] (–X–C(O)–R 6 ) m –X–C(O)– (III), or

[1022] (–C(O)–X–R 6 ) m –C(O)–X– (IV), preferably having at least one of the following portions

[1023] (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa), or

[1024] (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa),

[1025] or

[1026] The ester of a halogenated carboxylic acid, preferably chloroacetic acid, as defined above, with an alcohol or epoxide is reacted with a tertiary amine, said tertiary amine containing at least one of the following moieties:

[1027] (–X–C(O)–R 6 ) m –X–C(O)– (III), or

[1028] (–C(O)–X–R 6 ) m –C(O)–X– (IV), preferably having at least one of the following portions

[1029] (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa), or

[1030] (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa),

[1031] or

[1032] The epoxy-functionalized ethers and esters, preferably glycidyl ethers and esters, of alcohols or carboxylic acids as defined above are reacted with tertiary amines in the presence of an acid, said tertiary amine containing at least one of the following moieties:

[1033] (–X–C(O)–R 6 ) m –X–C(O)– (III), or

[1034] (–C(O)–X–R 6 ) m –C(O)–X– (IV), preferably having at least one of the following portions

[1035] (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa), or

[1036] (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa),

[1037] or

[1038] Reacting a hydrocarbon containing a tertiary amino group with an ester of a halogenated carboxylic acid as defined above, wherein the ester contains at least one of the following moieties:

[1039] (–X–C(O)–R 6 ) m –X–C(O)– (III), or

[1040] (–C(O)–X–R 6 ) m –C(O)–X– (IV), preferably having at least one of the following portions

[1041] (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa), or

[1042] (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa),

[1043] or

[1044] A hydrocarbon containing a tertiary amino group is reacted with an epoxy-functionalized ether and an ester as defined above in the presence of an acid, wherein the epoxy-functionalized ether and ester contain at least one of the following moieties.

[1045] (–X–C(O)–R 6 ) m –X–C(O)– (III), or

[1046] (–C(O)–X–R 6 ) m –C(O)–X– (IV), preferably having at least one of the following portions

[1047] (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa), or

[1048] (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa)

[1049] Among them, X and R 6 R 7 m and x are as defined above.

[1050] According to this embodiment, the following is preferred:

[1051] X = O,

[1052] R 6The group is independently selected from hexene, heptene, octene, nonene, decene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecanylene, octadecylene, nonadecanylene, eicosylene, icosylene, icosylene, tridecylene, and tetradecylene, or hexene, heptene, octene, nonene, decene, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, icosylene, eicosylene, icosylene, icosylene, tridecenyl, icosylene, and tetradecenyl, wherein the group is most preferably bonded to an adjacent C(O) group or O group via a terminal C atom, and if present,

[1053] R 7 The group is independently selected from hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, dodecyl, tridecyl, and tetradecyl, or hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanenyl, eicosenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanenyl, eicosenyl, dodecenyl, tridecenyl, and tetradecenyl, wherein the group is most preferably bonded to an adjacent C(O) group via a terminal C atom.

[1054] m is 1-10, preferably 1, 2, 3, 4 or 5.

[1055] It is even more preferred when X = 0,

[1056] R 6 Selected from hexadecylene, heptadecanylene, octadecylene, nonadecanylene, eicosylene, hexadecenylene, heptadecanylene, octadecenylene, nonadecanylene, eicosylene, and if present,

[1057] R 7 Selected from hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanenyl, and eicosenyl.

[1058] And m can be 1, 2, 3, 4 or 5.

[1059] According to this implementation, the following is the most preferred condition:

[1060] X = O,

[1061] R 6 Derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or hydroxyeicosenoic acid, and if present,

[1062] R 7 Derived from oleic acid, ricinoleic acid, or stearic acid

[1063] And m can be 1, 2, 3, 4 or 5.

[1064] In another preferred embodiment of the invention, a process for synthesizing compounds of general formula (I) is provided.

[1065] R 1 (–F) x (I)

[1066] Where R 1 N is attached to quaternized nitrogen atom + And R 1 (-F) x Having at least one part of the general formula (XIII), (XIV), (XIIIa) or (XIVa)

[1067] -R 10 (–X–C(O)–R 6 ) m –X–C(O)– (XIII)

[1068] -R 10 (–C(O)–X–R 6 ) m –C(O)–X– (XIV), preferably

[1069] -R 10 (–X–C(O)–R 6 ) m –X–C(O)–R 7 (XIIIa)

[1070] -R 10 (–C(O)–X–R 6 ) m –C(O)–X–R 7 (XIVa), where

[1071] Such compounds are obtained by reacting an alkyl halide with a tertiary amine having at least one moiety having the general formula (XIII), (XIV), (XIIIa), or (XIVa), wherein R 1 N is attached to quaternized nitrogen atom + And R 1 (-F) xIt has at least one part having the general formula (XIII), (XIV), (XIIIa), or (XIVa).

[1072] or

[1073] An ester of a halogenated carboxylic acid, preferably chloroacetic acid (the ester being formed from an alcohol or epoxide), is reacted with a tertiary amine having at least one moiety having the general formula (XIII), (XIV), (XIIIa), or (XIVa) to obtain such compounds as described above.

[1074] or

[1075] Epoxy-functionalized ethers and esters, preferably glycidyl ethers and esters, formed from alcohols or carboxylic acids as defined above, are reacted with a tertiary amine having at least one moiety having the general formula (XIII), (XIV), (XIIIa), or (XIVa) in the presence of an acid to obtain such compounds as described above.

[1076] or

[1077] Reacting a hydrocarbon containing a tertiary amino group with an ester of a halocarboxylic acid having at least one moiety of the general formula (XIII), (XIV), (XIIIa), or (XIVa) yields such compounds as described above, or

[1078] A hydrocarbon containing a tertiary amino group is reacted with an epoxy-functionalized ether and an ester, as defined above, having at least one moiety having the general formula (XIII), (XIV), (XIIIa), or (XIVa), in the presence of an acid to obtain such compounds as described above, wherein R 10 X, R 6 R 7 m and x are as defined above.

[1079] According to this embodiment, the following is preferred:

[1080] X = O,

[1081] R 6The group is independently selected from hexene, heptene, octene, nonene, decene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecanylene, octadecylene, nonadecanylene, eicosylene, icosylene, icosylene, tridecylene, and tetradecylene, or hexene, heptene, octene, nonene, decene, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, icosylene, eicosylene, icosylene, icosylene, tridecenyl, icosylene, and tetradecenyl, wherein the group is most preferably bonded to an adjacent C(O) group or O group via a terminal C atom, and if present,

[1082] R 7 The group is independently selected from hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, dodecyl, tridecyl, tridecyl, and tetradecyl, optionally substituted with a hydroxyl group, or hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanenyl, eicosenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecanenyl, octadecenyl, nonadecanenyl, eicosenyl, dodecenyl, tridecenyl, and tetradecenyl, wherein the group is most preferably bonded to an adjacent C(O) group via a terminal C atom.

[1083] R 1 It is an unsubstituted C1-C8 alkylene group that does not contain functional groups, or R 1 Linear C3-C50 alkylene groups derived from diglycidyl ether, glycerol diglycidyl ether, monodiglycidyl diglycidyl ether, monodiethylene glycol diglycidyl ether, or ethylene glycol diglycidyl ether having 3-10 (ethylene oxide) repeating units, and

[1084] m is 1-10, preferably 1, 2, 3, 4 or 5.

[1085] It is even more preferred when X = 0,

[1086] R 6 Selected from hexadecylene, heptadecanylene, octadecylene, nonadecanylene, eicosylene, hexadecenylene, heptadecanylene, octadecenylene, nonadecanylene, eicosylene, and if present,

[1087] R 7Selected from hexadecyl, heptadecanyl, octadecyl, nonadecanyl, eicosyl, hexadecenyl, heptadecanyl, octadecenyl, nonadecanenyl, and eicosenyl.

[1088] R 1 It is an unsubstituted C1-C8 alkylene group that does not contain functional groups, or R 1 It is a linear C3-C50 alkylene group derived from diglycidyl ether, glycerol diglycidyl ether, monodiglycidyl diglycidyl ether, monodiethylene glycol diglycidyl ether, or ethylene glycol diglycidyl ether having 3-10 (ethylene oxide) repeating units.

[1089] And m can be 1, 2, 3, 4 or 5.

[1090] According to this implementation, the following is the most preferred condition:

[1091] X = O,

[1092] R 6 Derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or hydroxyeicosenoic acid, and if present,

[1093] R 7 Derived from oleic acid, ricinoleic acid, or stearic acid

[1094] R 1 R1 is an unsubstituted C1-C8 alkylene group without functional groups, or R1 is a linear C3-C50 alkylene group derived from diglycidyl ether, glycerol diglycidyl ether, monodiglycidyl diglycidyl ether, or diethylene glycol diglycidyl ether.

[1095] And m can be 1, 2, 3, 4 or 5.

[1096] The present invention further relates to the use of the polymeric fatty acid compounds of general formula (I) in cosmetic formulations for skin and hair care, particularly conditioners and shampoos, in polishing agents for treating and coating hard surfaces, in formulations for drying automobiles and other hard surfaces, for example, after automatic washing, for finishing fabrics and fabric fibers, as separate softeners for use after fabrics have been washed with nonionic or anionic / nonionic detergent formulations, as softeners in formulations for washing fabrics based on nonionic or anionic / nonionic surfactants, and as a means of preventing or removing wrinkles in fabrics.

[1097] The present invention further relates to the use of the above-mentioned polymeric fatty acid compounds in cosmetic compositions for treating fibers, preferably amino acid-based fibers, more preferably human hair, said cosmetic compositions being used in particular for strengthening hair, for maintaining hair color, for enhancing hair shine, for enhancing hair color, for protecting hair color, for styling hair, especially for curling and straightening hair, for conditioning hair, for smoothing or softening hair, for improving hair manageability, especially for improving hair combability, anti-frizz and antistatic properties.

[1098] Preferred compositions according to the present invention are cosmetic compositions for treating hair, selected from hair shampoo compositions, hair care compositions, hair conditioning compositions, hair strengthening compositions, hair coloring or dyeing compositions, compositions for improving hair combability, anti-frizz compositions, rinsing and leave-in hair compositions.

[1099] The present invention further relates to compositions containing at least one of the polymeric fatty acid compounds and at least one additional component commonly used in such compositions.

[1100] The following provides numerous typical examples of these types of compositions in which the polymeric fatty acid compounds of the present invention can be advantageously used. Typical adjuvants in these types of compositions are, for example, those materials described below: A. Domsch: Die kosmetischen Praeparate [Cosmetic Preparations] Vol. I and II, 4th edition, Verl. fuer chem. Industrie [Publishers for the Chemical Industry], U. Ziolkowsky KG, Augsburg; and the International Cosmetic Ingredient Dictionary and Handbook, 7th edition, 1997; J.A. Wenninger, GN. McEwen, Vol. I-4, The Cosmetic, Toiletry and Fragnance Association, Washington DC.

[1101] In particular, the present invention relates to compositions as defined above for treating hair, selected from hair shampoo compositions, hair conditioning compositions, hair strengthening compositions, hair coloring or dyeing compositions, hair combability improving compositions, anti-frizz compositions, rinsing and leave-in hair compositions. In the following formulations, the term "polymeric fatty acid compound of the present invention" is used to refer to compounds as defined above.

[1102] Example of a formulation:

[1103] Anionic shampoo

[1104] This formulation example is intended as a base formulation. Anionic shampoos typically contain, but are not limited to, the following components: alkyl sulfates, alkyl ether sulfates, sodium lauryl sulfate, sodium lauryl ether sulfate, ammonium lauryl sulfate, ammonium lauryl ether sulfate, TEA-lauryl sulfate, TEA-lauryl ether sulfate, alkylbenzene sulfonates, α-olefin sulfonates, alkane sulfonates, sulfosuccinates, N-acyl taurate, glyceryl ester sulfates, sulfated alkanolamides, carboxylates, N-acyl-amino acid salts, organosilicones, etc.

[1105]

[1106] Nonionic shampoo

[1107] This formulation example is intended as a base formulation. Nonionic shampoos typically contain, but are not limited to, the following components: monoalkanolamides, monoethanolamides, monoisopropanolamides, polyhydroxy derivatives, sucrose monolaurates, polyglycerol ethers, amine oxides, polyethoxylated derivatives, sorbitol derivatives, organosilicones, etc.

[1108] Components weight% lauramide DEA 10.00-30.00 Laurethamide oxide 5.00-20.00 Cocamide MEA 0.00-5.00 Dimethicone Copolymer 0.00-5.00 The polymeric fatty acid compounds of the present invention 0.50-5.00 preservative 0.00-0.50 essence 0.00-5.00 Deionized water Appropriate amount to achieve 100% Sodium chloride Appropriate amount

[1109] Sexual Shampoo

[1110] This formulation example is intended as a base formulation. Formulations in this category typically contain, but are not limited to, the following components: N-alkyl-iminodipropionate, N-alkyl-iminopropionate, amino acids, amino acid derivatives, amide betaine, imidazoline derivatives, sulfobetaine, sulfonate betaine, betaine, organosilicon, etc.

[1111] Components weight% PEG-80-Sorbitol Laurate 10.00-30.00 Lauroyl amphoteric glycinate 0.00-10.00 Cocoylaminopropyl-hydroxysulfonic acid betaine 0.00-15.00 PEG-150-Dilaurate 0.00-5.00 Lauryl ether-13-carboxylate 0.00-5.00 The polymeric fatty acid compounds of the present invention 0.50-5.00 essence 0.00-5.00 Deionized water Appropriate amount to achieve 100% Sodium chloride Appropriate amount

[1112] cationic shampoo

[1113] This formulation example is intended only as a basic formulation. Formulations in this category typically contain, but are not limited to, the following components: bis-quaternary ammonium compounds, bis-(trialkylammonium acetyl)diamines, amides, ammonium alkyl esters, organosilicones, etc.

[1114]

[1115]

[1116] hairspray

[1117] This formulation example is intended only as a basic formulation. Formulations in this category typically contain, but are not limited to, the following components: fatty acids, fatty acid esters, ethoxylated fatty acids, ethoxylated fatty acid esters, fatty alcohols, ethoxylated fatty alcohols, glycols, glycol esters, glycerol, glyceryl esters, lanolin, lanolin derivatives, mineral oil, petrolatum, lecithin, lecithin derivatives, waxes, wax derivatives, cationic polymers, proteins, protein derivatives, amino acids, amino acid derivatives, humectants, thickeners, organosilicones, etc.

[1118] Components weight% Cetearyl alcohol polyether-20 0.10-10.00 Stearyl alcohol polyether-20 0.10-10.00 Stearyl alcohol 0.10-10.00 Stearoylaminopropyl-dimethylamine 0.00-10.00 Diceryl dimethylammonium chloride 0.00-10.00 The polymeric fatty acid compounds of the present invention 0.50-5.00 Cyclopentasiloxane 0.00-5.00 Dimethicone 0.00-5.00 preservative 0.00-0.50 essence 0.00-5.00 Deionized water Appropriate amount to achieve 100%

[1119] "Clear Rinse-Off" setting agent

[1120] This formulation example is intended as a base formulation. Formulations in this category typically contain, but are not limited to, the following components: fatty acids, fatty acid esters, ethoxylated fatty acids, ethoxylated fatty acid esters, fatty alcohols, ethoxylated fatty alcohols, glycols, glycol esters, glycerol, glyceryl esters, lanolin, lanolin derivatives, mineral oil, petrolatum, lecithin, lecithin derivatives, waxes, wax derivatives, cationic polymers, proteins, protein derivatives, amino acids, amino acid derivatives, humectants, thickeners, organosilicones, etc.

[1121] Components weight% glycerin 0.10-10.00 Cetrimonium chloride 0.00-10.00 The polymeric fatty acid compounds of the present invention 0.50-5.00 Hydroxyethyl cellulose 0.00-5.00 preservative 0.00-0.50 essence 0.00-5.00 Deionized water Appropriate amount to achieve 100%

[1122] Foam styling products for hair

[1123] This formulation example is intended as a base formulation. Formulations in this category contain, but are not limited to, the following components: fatty acids, fatty acid esters, ethoxylated fatty acids, ethoxylated fatty acid esters, fatty alcohols, ethoxylated fatty alcohols, glycols, glycol esters, glycerol, glyceryl esters, lanolin, lanolin derivatives, mineral oil, petrolatum, lecithin, lecithin derivatives, waxes, wax derivatives, cationic polymers, proteins, protein derivatives, amino acids, amino acid derivatives, humectants, thickeners, silicones, solvents, ethanol, isopropanol, isoparaffin solvents, butane, propane, isobutane, CFC fluorinated aerosol propellants, dimethyl ether, compressed gases, etc.

[1124] Components weight% The polymeric fatty acid compounds of the present invention 0.50-5.00 Nonylphenol polyether-15 0.00-2.00 Nonylphenol polyether-20 0.00-2.00 aerosol propellant 0.00-20.00 preservative 0.00-0.50 essence 0.00-5.00 Deionized water Appropriate amount to achieve 100%

[1125] Pump spray for hair (styling agent)

[1126] This formulation example is intended only as a basic formulation. Formulations in this category typically contain, but are not limited to, the following components: fatty acids, fatty acid esters, ethoxylated fatty acids, ethoxylated fatty acid esters, fatty alcohols, ethoxylated fatty alcohols, glycols, glycol esters, glycerol, glyceryl esters, lanolin, lanolin derivatives, mineral oil, petrolatum, lecithin, lecithin derivatives, waxes, wax derivatives, cationic polymers, proteins, protein derivatives, amino acids, amino acid derivatives, humectants, thickeners, silicones, solvents, ethanol, isopropanol, isoparaffin solvents, etc.

[1127] Components weight% The polymeric fatty acid compounds of the present invention 0.50-5.00 Cyclomethyl silicone oil 0.00-80.00 ethanol 0.00-80.00 preservative 0.00-0.50 essence 0.00-5.00 Deionized water Appropriate amount to achieve 100%

[1128] Hair styling spray

[1129] This formulation example is intended as a base formulation. Formulations in this category typically contain, but are not limited to, the following components: fatty acids, fatty acid esters, ethoxylated fatty acids, ethoxylated fatty acid esters, fatty alcohols, ethoxylated fatty alcohols, glycols, glycol esters, glycerol, glyceryl esters, lanolin, lanolin derivatives, mineral oil, petrolatum, lecithin, lecithin derivatives, waxes, wax derivatives, cationic polymers, proteins, protein derivatives, amino acids, amino acid derivatives, humectants, thickeners, silicones, solvents, ethanol, isopropanol, isoparaffin solvents, butane, propane, isobutane, CFC fluorinated aerosol propellants, dimethyl ether, compressed gases, etc.

[1130] Components weight% The polymeric fatty acid compounds of the present invention 0.50-5.00 Cyclomethyl silicone oil 0.00-80.00 ethanol 0.00-50.00 aerosol propellant 0.00-50.00 preservative 0.00-0.50 essence 0.00-5.00 Deionized water Appropriate amount to achieve 100%

[1131] Hair gel styling product

[1132] This formulation example is intended as a basic formulation. Formulations in this category typically contain, but are not limited to, the following components: thickeners, cellulose derivatives, acrylic derivatives, fixative polymers, conditioning chemicals, glycols, glycol esters, glycerol, glyceryl esters, lanolin, lanolin derivatives, mineral oil, petrolatum, lecithin, lecithin derivatives, waxes, wax derivatives, cationic polymers, proteins, protein derivatives, amino acids, amino acid derivatives, humectants, silicones, solvents, ethanol, isopropanol, isoparaffin solvents, etc.

[1133]

[1134]

[1135] Rinse-off conditioner

[1136] This formulation example is intended as a base formulation. Formulations in this category typically contain, but are not limited to, the following components: hydrocarbon-based cationic conditioners, silicone-based cationic conditioners, high-melting-point fatty compounds, low-melting-point oily ester compounds, thickeners, cellulose derivatives, fixative polymers, ethylene glycol, propylene glycol, glycol esters, glycerol, glyceryl esters, monohydroxy alcohols, polyhydroxy alcohols, cationic polymers, nonionic and betaine co-emulsifiers, silicones, complexing agents, solvents, flavorings, vitamins, etc.

[1137]

[1138] Hair styling gel

[1139] This formulation example is intended as a base formulation. Formulations in this category typically contain, but are not limited to, the following components: fixative polymers, lacquer, acrylic acid derivatives, cellulose derivatives, vinyl derivatives, conditioning chemicals, glycols, glycol esters, glycerin, glyceryl esters, lanolin, lanolin derivatives, mineral oil, petrolatum, lecithin, lecithin derivatives, waxes, wax derivatives, cationic polymers, proteins, protein derivatives, amino acids, amino acid derivatives, humectants, thickeners, silicones, solvents, ethanol, isopropanol, isoparaffin solvents, etc.

[1140]

[1141]

[1142] Hair styling spray

[1143] This formulation example is intended as a base formulation. Formulations in this category typically contain, but are not limited to, the following components: fixative polymers, spray-setting agents, vinyl derivatives, fatty acids, fatty acid esters, ethoxylated fatty acids, ethoxylated fatty acid esters, fatty alcohols, ethoxylated fatty alcohols, glycols, glycol esters, glycerol, glyceryl esters, lanolin, lanolin derivatives, mineral oil, petrolatum, lecithin, lecithin derivatives, waxes, wax derivatives, cationic polymers, proteins, protein derivatives, amino acids, amino acid derivatives, humectants, thickeners, silicones, solvents, ethanol, isopropanol, isoparaffin solvents, butane, propane, isobutane, CFC fluorinated aerosol propellants, dimethyl ether, compressed gases, etc.

[1144] Components weight% The polymeric fatty acid compounds of the present invention 0.50-5.00 Cyclomethyl silicone oil 0.00-80.00 Fixative 0.10-10.00 ethanol 0.00-50.00 aerosol propellant 0.00-50.00 preservative 0.00-0.50 essence 0.00-5.00 Deionized water Appropriate amount to achieve 100%

[1145] Pump spray for hair styling

[1146] This formulation example is intended as a base formulation. Formulations in this category typically contain, but are not limited to, the following components: vinyl derivatives, fixative polymers, spray-setting agents, fatty acids, fatty acid esters, ethoxylated fatty acids, ethoxylated fatty acid esters, fatty alcohols, ethoxylated fatty alcohols, glycols, glycol esters, glycerol, glyceryl esters, lanolin, lanolin derivatives, mineral oil, petrolatum, lecithin, lecithin derivatives, waxes, wax derivatives, cationic polymers, proteins, protein derivatives, amino acids, amino acid derivatives, humectants, thickeners, silicones, solvents, ethanol, isopropanol, isoparaffin solvents, butane, propane, isobutane, CFC fluorinated aerosol propellants, dimethyl ether, compressed gases, etc.

[1147] Components weight% The polymeric fatty acid compounds of the present invention 0.50-5.00 Cyclomethyl silicone oil 0.00-80.00 Fixative 0.10-10.00 ethanol 0.00-50.00 preservative 0.00-0.50 essence 0.00-5.00 Deionized water Appropriate amount to achieve 100%

[1148] In the field of hair care, the use of the polymeric fatty acid derivatives detailed in this invention has produced favorable results in terms of strength, shine, fixation, body volume, volume, moisture control, color retention, protection against environmental factors (UV, salt water, etc.), manageability, combability, anti-frizz, antistatic properties, and dyeing ability.

[1149] Other formulation examples:

[1150] In the following formulation examples, all values ​​given represent amounts in terms of "weight % of the whole composition" unless otherwise stated.

[1151] Naturally derived Crystal Clear, betaine-free conditioning shampoo

[1152]

[1153] program

[1154] Add Polyquta 400KC to the vortex of water and mix until it is fully dispersed and clear. Heat phase A to 40-45°C. Homogenize Pureact WS Conc, Pureact Gluco L, and Pureact MS-CG by heating to 40-45°C and mixing the products before adding them to the master vessel. Then, add the components of phase B and mix until homogeneous and clear. Slowly add Surfac SB09 and the polymeric fatty acid compound of the present invention (phase C) to the master vessel and mix until homogeneous. Cool the vessel to below 40°C, then add the preservative and mix until the mixture is clear and homogeneous. Add the flavoring and mix until it is fully emulsified and clear. Adjust the pH to 4.2-4.7 with citric acid solution (50% w / w) if necessary. Add a small amount of sodium chloride (0.2% w / w) if necessary until the desired viscosity is obtained.

[1155] Fatal Attraction Hair Mist

[1156] program

[1157]

[1158]

[1159] program

[1160] Add phase A to the vessel with gentle stirring. Mix until clear. Add phase B to phase A with stirring at room temperature. Mix until homogeneous. While continuing to stir, slowly add phase C to phases A / B using a suitable mixer. When the mixture is homogeneous, adjust the pH to 5.00–5.50 with phase D.

[1161] Have A Peachy Day Jelly Shampoo

[1162]

[1163]

[1164] program

[1165] In the master vessel, combine the components of phase A in the order of formulation under shear mixing and heat to 140°F–149°F (60–65°C). Add phase B to phase A in the order of formulation under continuous mixing. Once the solution thickens, neutralize to the desired pH. In a separate vessel, combine the components of phase C and heat to 140°F–149°F (60–65°C). Once homogenized, add phase C to phases AB under paddle mixing. Combine phase D in a separate vessel and then add it to the master vessel under continuous mixing. Transfer the mixture to the final container.

[1166] PEG-free shampoo

[1167]

[1168]

[1169] program

[1170] Mix the components of phase A while heating to 70°C with moderate paddle stirring until homogeneous. Add phase B to phase A and mix until homogeneous. Heat deionized water for phase C to 65-70°C and dissolve Quatrisoft Polymer LM-200. Once Quatrisoft Polymer LM-200 is completely dissolved, slowly add Tauranol I-78. Slowly add phase C to phase AB. Mix until homogeneous and cool to 50°C. Add phase D to phases ABC in the listed order with moderate paddle stirring. Cool the mixture to room temperature.

[1171] Repair shampoo sticks

[1172]

[1173]

[1174] program

[1175] In the master container, add the components of phase A while gently mixing and heat to 70-75°C. Add phase B to phase A while continuing to mix and maintaining 70-75°C. Add phase C to phase AB while continuing to mix and maintaining 70-75°C. Cool the batch when it is homogeneous. Add phase D to the batch. Fill the preheated rod when the batch has cooled to 45°C. Place the rod in the refrigerator for 12-24 hours before first use.

[1176] Frozen Yogurt Hair Mask

[1177]

[1178] program

[1179] In the main beaker, weigh phase A and heat to 75°C. Sprinkle phase B onto the aqueous phase and wait until the carbopol is completely hydrated. Homogenize it, add phase C to neutralize, and homogenize again. In the auxiliary container, weigh phase D and heat to 75°C. Slowly add D to the aqueous phase with high stirring. Then, cool the emulsion with moderate stirring. At 35°C, add phases E and F and homogenize.

[1180] Crystal Clear Healthy Hair Shampoo

[1181]

[1182] program

[1183] Add water to a suitable vessel. While heating the water to 80-85°C, add Hostapon SCI, Glucotain Plus, and Amphosol CS-50. Mix until homogeneous at 80-85°C and remove from heat. In a separate beaker, mix Celquat 240C, Glucquat 125, and deionized water until homogeneous. Once homogeneous, add the Celquat / Gluquat blend to the master batch (phase A). Add phase C components one by one and mix thoroughly. Adjust the pH of the solution to 6.0-6.5 with 20% citric acid or 20% NaOH. Fill the batch to 100% with deionized water.

[1184] Hair Repair Serum

[1185]

[1186] program:

[1187] In separate vessels, while the mixture is heated to 50°C, add each component of phase A individually. Mix until homogeneous and homogeneous. Cool the mixture to a temperature <35°C. In separate vessels, while the mixture is heated, add each component of phases B and C individually and mix until homogeneous. When the main vessel has cooled to 35°C, add phases B and C to phase A. Mix until homogeneous. Add phase D to the main vessel to adjust the pH to 4.80–5.40. Add phase E to the main vessel with gentle stirring and mix until homogeneous.

[1188] Hair Repair Serum with Keratrix

[1189]

[1190] program

[1191] In separate vessels, while mixing, add each component of phase A individually, while heating to 50°C. Mix until homogeneous and homogeneous, and cool the mixture to <35°C. In separate vessels, separately, add each component of phases B and C individually, while mixing, and mix until homogeneous. Once the main vessel has cooled to 35°C, add phases B and C to phase A and mix until homogeneous. Add phase D to the main vessel to adjust the pH to 4.80–5.40. Add phase E to the main vessel with gentle stirring and mix until homogeneous.

[1192] Put More Life In Your Hair ClayMask

[1193]

[1194]

[1195] program:

[1196] In a paddle mixer, combine the components of phase A in the main vessel according to the formulation order and heat to 60-70°C. In a separate vessel, combine the components of phase B in the formulation order and heat to 60-70°C using a paddle mixer. Once phases A and B are completely homogenized, add phase B to phase A while continuously mixing. Once completely dispersed, stop heating. Once the temperature reaches 35-40°C, add phase C to phases AB while continuously mixing. Add phase D to phases ABC, stop mixing, and switch to a homogenizer. Homogenize the mixture for 10-30 seconds. Once complete, transfer the mixture to a storage vessel.

[1197] Detox Hair Sleeping Pack

[1198]

[1199] program

[1200] In the master container, add each component of phase A individually and gently mix until the mixture is homogeneous. Disperse phase B in the container under shear mixing conditions. When the batch is homogeneous, add each component of phase C individually, mixing until homogeneous before adding the next component. Adjust the pH to 5.40–6.00 with sodium hydroxide and mix until the gel is homogeneous.

[1201] Clean Beauty Light & Clean Conditioner

[1202]

[1203] program

[1204] Heat phase A to 75°C with stirring. In a separate vessel, heat the components of phase B to 75°C with stirring. Add phase B to phase A and continue mixing for 10 minutes. Remove the heat and continue stirring until the product reaches 40°C. Combine the components of phase C and mix thoroughly with moderate stirring. Add phase C to phases A / B at 40°C and continue stirring until the product reaches room temperature.

[1205] It lathers gently. It is a gentle, bubbly, italic shampoo.

[1206]

[1207] program

[1208] Add water to a mixing vessel and sprinkle polyquaternium-10 (B) into the water, mixing until clear. With the mixture moderately mixed, pour Iselux Ultra Mild (C) into the main vessel. Add phase (D) to the batch. Mix until clear, then add the desired fragrance and preservatives and adjust the pH using citric acid (50% w / w solution) (G).

[1209] Coconut Dream Conditioner

[1210]

[1211]

[1212] program

[1213] Mix the components of phase A and heat to 80°C. Blend the components of phase B at 80°C. Add phase B to phase A. Cool to 40°C and add phase C. Cool further, add phase D, and adjust the pH of the mixture to 4.3–4.7.

[1214] Glycolic acid shampoo

[1215]

[1216]

[1217] program

[1218] In the main vessel, add phase A and mix until homogeneous. Add phase B to phase A. In the auxiliary vessel, combine phase C and then slowly add it to phases AB, ensuring the pH is >4. Add the preservative to phases ABC. Continue mixing if the batch is initially discontinuous. Slowly add the surfactant to phases ABCD. The batch will become homogeneous and the viscosity will increase. Finally, add the fragrance.

[1219] 2-phase superhydration hair treatment

[1220]

[1221]

[1222] program

[1223] Components of phase B are blended and phase A is added simultaneously. Then, components of phase C are added to phase AB. Components of phase D are blended and added to phases ABC under high shear conditions. Then, phase E is added.

[1224] Cleansing and Nourishing Shampoo

[1225]

[1226]

[1227] program

[1228] Heat phase A to 75-80°C. Premix phase B and add it to a portion of A while mixing at a medium speed. Cool it to 40°C and add phase C. Check the pH and adjust it with citric acid solution if necessary.

[1229] hair wax formulation

[1230]

[1231]

[1232] program

[1233] Prepare phase A and heat it to 75-80°C. Prepare phase B and heat it to 70-75°C. Add phase B to phase A and homogenize it for several minutes using a suitable dispersion unit (e.g., Silverson, Ultra Turrax, etc.). Cool it to 40°C, and add phases C and D and mix for several minutes. Cool the mixture to room temperature.

[1234] Portable (On-the-Go) Hair Cream (Sherbet)

[1235]

[1236] program

[1237] Add phase A to the vessel while gently stirring and heating to 45-50°C. Mix until homogeneous. Add phase B to phase A while stirring. Mix until homogeneous. Add phase C to phases A / B while continuing to stir. When homogeneous, add each component of phase D individually to phases A / B / C while gently stirring. Mix between each addition.

[1238] Dreamy Curls 24-Hour Weightless Foam

[1239]

[1240] program:

[1241] Add water to the main container and mix using a paddle stirrer. Add Styleze ES-1 to the vortex to disperse. Add citric acid and mix for approximately 10-15 minutes. Add Benecel E4M and mix until no particles are visible. Add the polymeric fatty acid compound of the present invention, Amphosol CA, glycerol, and Optiphen BSB-W one at a time and mix until homogeneous.

[1242] Sea Salt 2-in-1 Scalp Treatment Shampoo

[1243]

[1244]

[1245] program

[1246] Polyquaternium-10 is slowly added to water. Next, glycerol is added to the master vessel and mixed until fully dispersed and clear. Then, phase (B) is added and heated to 65-70°C and mixed until homogeneous. Phase (C) is added, maintaining the temperature at 65-70°C and mixed until homogeneous. The pH is adjusted to 5.5-6.0 with citric acid (50% w / w solution). Phase (E) is added and mixed until homogeneous. Phase (F) is added while maintaining the temperature at ~65°C and mixed until the desired structure is obtained. Heating is stopped and the mixture is cooled to 30°C. Phase (G) is then added while still mixed.

[1247] Moisturizing and Shiny Hair Essence

[1248]

[1249]

[1250] program:

[1251] In the main vessel, add each component of phase A individually and gently mix until the mixture is homogeneous and transparent. Add the remaining phases individually, mixing until homogeneous before each addition.

[1252] A D5-free makeup primer containing argan oil.

[1253]

[1254] program

[1255] The components of phase B are added to phase A and mixed under low to medium shear conditions.

[1256] The components of phase C are blended and added to phase AB.

[1257] Example:

[1258] (Percentages refer to weight, unless otherwise stated).

[1259] As used in this article, the term "castor oil" generally refers to ricinoleic acid triglyceride.

[1260] A review of the nomenclature used for the lactone moiety and lactone compounds in this article.

[1261] In the nomenclature used to represent the structure of a lamellar group as used in the following examples (which refers to a compound from which the lamellar moiety is at least formally obtained by esterification), the carboxylic acids from which the lamellar moiety is at least formally derived are given in parentheses in sequence. Where a series of several subunits derived from the same acid are present in the lamellar moiety and these are indicated in parentheses, with the subscript integer indicating the number of repeating units, the carboxylic acid is given in square brackets.

[1262] Note that the specific carboxylic acids given in parentheses or square brackets are not randomly assembled, but rather each has a specific sequence of hydroxy-carboxylic acid-derived residues and carboxylic acid-derived residues as shown in the terminology used. The last carboxylic acid given in the terminology within parentheses or square brackets is the terminal carboxylic acid of the lactone moiety. From the beginning to the end of the terminology within parentheses or square brackets, the order of the carboxylic acid residues linked by the ester group is shown as the correct order and number of residues contained.

[1263] For example, the term "(12-hydroxystearic acid-ricinoleic acid-oleic acid)" refers to a crosslactone moiety in which the 12-hydroxystearic acid molecule is formally linked to the carboxylic acid group of the ricinoleic acid molecule via its OH group by forming an ester group. The hydroxyl group of the ricinoleic acid group is linked to the oleic acid molecule by forming an ester group with the carboxylic acid group of the oleic acid molecule. In this example, oleic acid is considered as the terminal group of this specific crosslactone moiety, as if the crosslactone moiety were a substituent at a higher level (i.e., a more complex molecule), and the crosslactone moiety is generally linked to the entire structure via a carboxylic acid group linked to the previously mentioned residue used for the term crosslactone moiety. In this case, this is the previously mentioned 12-hydroxystearic acid residue, and the oleic acid residue is the terminal group of the crosslactone moiety.

[1264] Therefore, when the terminology used refers to carboxyl chloride with a crosslactone structure, the acyl chloride group must be formed by the carboxylic acid group of the carboxylic acid residue mentioned in parentheses, that is, the carboxylic acid group furthest from the terminal group.

[1265] When using terms such as “dimer” or “trimer”, this refers to the number of carboxylic acid-derived subunits of the lactone moiety.

[1266] Similarly, the term "[(ricinoleic acid)2-oleic acid]lactone" refers to a lamellar moiety or compound in which a ricinoleic acid molecule or residue is formally linked to a carboxylic acid molecule via its OH group by forming an ester group. The hydroxyl group of the latter ricinoleic acid group is linked to the oleic acid molecule by forming an ester group with the carboxylic acid group. Oleic acid is considered the terminal group of this specific lamellar moiety as if the lamellar moiety were a substituent at a higher level (i.e., a more complex molecule), the lamellar moiety being linked to the entire structure via a carboxylic acid group linked to the previously mentioned ricinoleic acid residue, and the oleic acid residue being the terminal group of the lamellar moiety.

[1267] In cases where the lamellar moiety is linked by a linking group via an ester or amide group (e.g., in [(ricinoleic acid)6-succinic acid–(ricinoleic acid)6], residues derived from succinic acid are linked to two ricinoleic acid lamellar groups via ester groups on each side), this is indicated by incorporating the name of the parent compound into the terminology applied to the entire lamellar structure. Thus, a comprehensive terminology indicating the sequence of carboxylic acid residues is provided.

[1268] It should be noted further that the exact structure of the lactone is primarily elucidated by the structural formula (which is adequately provided for the compounds of the examples), and the structure of the compounds of the examples can also be clearly obtained by those skilled in the art through the detailed experimental procedures provided.

[1269] The term "commercially available polyglycerol-polyricinoleate" refers to... PGPR 4150, a commercially available polyglycerol-polyricinoleate manufactured by Palsgaard A / S, is detailed below:

[1270] Polyglycerol-polyricinoleate (E476) is a pale yellow, viscous liquid; viscosity reduction capacity: 74-87; maximum acid value: 3 mg KOH / g; hydroxyl value: 80-100 mg KOH / g; refractive index at 65°C: 1.4630-1.4665; iodine value: 72-103 gI2 / 100g; saponification value: 170-210 mg KOH / g; polyglycerol composition: diglycerol, triglycerol, and tetraglycerol, at least 75%; polyglycerol equal to or longer than hexaheptaglycerol, at most 10%.

[1271] Synthesis Example 1

[1272] Synthesis of (ricinoleic acid-oleic acid) lactone dimer

[1273] 225 g (0.75 mol) of ricinoleic acid was placed in a 1000 ml four-necked flask under a nitrogen atmosphere at room temperature. While stirring, 226.85 g (0.75 mol) of oleoyl chloride was slowly added over 1.5 h. The temperature was increased from 22 °C to 32 °C. The temperature increase was accompanied by the formation of bubbles, indicating the formation of HCl. The temperature was maintained at 32 °C for another 2 h, then increased to 50 °C and maintained therefore for 1 h. Volatile substances were removed under reduced pressure (40 °C / 2 h / 20 mmHg). 1 The conversion rate of the OH groups was determined by 100% using 1H NMR spectroscopy.

[1274] A light brown, transparent oil with the following basic structure is obtained:

[1275]

[1276] Synthesis Example 2

[1277] Synthesis of [(ricinoleic acid)2-oleic acid]lactone trimer

[1278] In a 250 ml four-necked flask equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas outlet tube, 34.87 g (0.293 mol) of SOCl2 was placed at room temperature under a nitrogen atmosphere. While stirring, 110 g (0.195 mol) of the lactone dimer from Synthesis Example 1 was slowly added over 1 h. At the end of this addition, the temperature was raised to 80 °C. The temperature was maintained at 80 °C for 1 h. Volatile substances were removed under reduced pressure (80 °C / 2 h / 20 mmHg). The vacuum was broken using nitrogen, and 57.75 g (0.195 mol) of ricinoleic acid was added to the carboxyl chloride intermediate at 80 °C for 45 min. This temperature was maintained for 2 h. Volatile substances were removed under reduced pressure (40 °C / 2 h / 20 mmHg). 1 The conversion rate of the OH groups was determined by 100% using 1H NMR spectroscopy.

[1279] A light brown, transparent oil with the following basic structure is obtained:

[1280]

[1281] Synthesis Example 2a

[1282] Synthesis of [(ricinoleic acid)2-stearic acid]lactone trimer

[1283] Two 250ml three-necked flasks, A and B, equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas outlet tube, were rinsed with nitrogen.

[1284] Bottle A is used to react fatty acyl chlorides with ricinoleic acid to produce extended-chain fatty ester acids. The subsequent addition of SOCl2 produces the corresponding fatty ester acyl chlorides.

[1285] Bottle B is used to react the formed fatty ester acyl chloride with ricinoleic acid to produce a chain-extended fatty ester acid. The subsequent addition of SOCl2 produces the corresponding fatty ester acyl chloride. This fatty acyl chloride is transferred back to bottle A and reacted with fresh ricinoleic acid. The above cycle can be repeated until the hexamer lactone [(ricinoleic acid)5-stearic acid] is prepared.

[1286] The general procedure for the synthesis of chain-extended fatty acid esters:

[1287] The calculated amount of ricinoleic acid was placed in a flask. An equimolar amount of fatty acid ester chloride was slowly added at room temperature. To complete the reaction, the temperature was raised to 80°C for 3 hours. 1 1H NMR spectroscopy confirmed complete conversion of the OH group.

[1288] The general procedure for the synthesis of fatty acid ester chlorides:

[1289] The calculated amount of fatty acid esters was placed in a flask. SOCl2 (three times excess) was slowly added at room temperature. The mixture was then heated to 80°C and maintained at this temperature for 3 hours. Afterward, excess SOCl2 was removed under reduced pressure (80°C / 2 hours / 20 mmHg). 1 1H NMR spectroscopy confirmed that the C(O)OH group was completely converted into the C(O)Cl group.

[1290] The table below summarizes the materials and quantities used.

[1291]

[1292] Note: When referring to the castor oil group, the term "rici" is used instead of the term "ricinoleic acid".

[1293] The formula for [(rici)2-stearic acid] is as follows:

[1294]

[1295] Synthesis Example 2b

[1296] Synthesis of (ricinoleic acid-12-hydroxystearic acid-oleic acid)lactone trimer

[1297] Repeat the procedure outlined in Example 2a of the synthesis.

[1298] The table below summarizes the materials and quantities used.

[1299]

[1300] Note: When referring to the castor oil group, the term "rici" is used instead of the term "ricinoleic acid", and when referring to the 12-hydroxystearic acid group, the term "12-hydroxy-stea" is used instead of the term "12-hydroxystearic acid".

[1301] The formula for rici-(12-hydroxystea)-oleic acid is as follows:

[1302]

[1303] Synthesis Example 2c

[1304] Synthesis of (12-hydroxystearic acid-ricinoleic acid-oleic acid)lactone trimer

[1305] Repeat the procedure outlined in Example 2a of the synthesis.

[1306] The table below summarizes the materials and quantities used.

[1307]

[1308] Note: When referring to the castor oil group, the term "rici" is used instead of the term "ricinoleic acid", and when referring to the 12-hydroxystearic acid group, the term "12-hydroxy-stea" is used instead of the term "12-hydroxystearic acid".

[1309] The formula for (12-hydroxystea-rici-oleic acid) is as follows:

[1310]

[1311] Synthesis Example 3

[1312] Synthesis of [(ricinoleic acid)5-oleic acid]lactone hexamer and the corresponding [(ricinoleic acid)5-oleic acid]acyl chloride hexamer

[1313] Rinse two 100ml three-necked flasks, A and B, equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas outlet tube, with nitrogen.

[1314] Bottle A is used to react fatty acyl chlorides with ricinoleic acid to produce extended-chain fatty ester acids. The subsequent addition of SOCl2 produces the corresponding fatty ester acyl chlorides.

[1315] Bottle B is used to react the formed fatty ester acyl chloride with ricinoleic acid to produce a chain-extended fatty ester acid. The subsequent addition of SOCl2 produces the corresponding fatty ester acyl chloride. This fatty acyl chloride is transferred back to bottle A and reacted with fresh ricinoleic acid. The above cycle is repeated until the hexamer lactone [(ricinoleic acid)5-oleic acid] is prepared.

[1316] The general procedure for the synthesis of chain-extended fatty acid esters:

[1317] The calculated amount of ricinoleic acid was placed in a flask. An equimolar amount of fatty acid ester chloride was slowly added at room temperature. To complete the reaction, the temperature was raised to 80°C for 3 hours. 1 ¹H NMR spectroscopy confirmed that the OH groups of ricinoleic acid were completely converted into esters.

[1318] The general procedure for the synthesis of fatty acid ester chlorides:

[1319] The calculated amount of fatty acid esters was placed in a flask. SOCl2 (three times excess) was slowly added at room temperature. The mixture was then heated to 80°C and maintained at this temperature for 3 hours. Afterward, excess SOCl2 was removed under reduced pressure (80°C / 2 hours / 20 mmHg). 1 1H NMR spectroscopy confirmed that the C(O)OH group was completely converted into the C(O)Cl group.

[1320] The table below summarizes the materials and quantities used.

[1321]

[1322] Note: When referring to the castor oil group, the term "rici" is used instead of the term "ricinoleic acid", and when referring to the 12-hydroxystearic acid group, the term "12-hydroxy-stea" is used instead of the term "12-hydroxystearic acid".

[1323] A light brown, transparent oil with the following structure [(rici)5-oleic acid] was obtained:

[1324]

[1325] The corresponding [(rici)5-oleic acid]acyl chloride has the following structure:

[1326]

[1327] Synthesis Example 4

[1328] Synthesis of branched bis-[(ricinoleic acid)2-oleic acid]lactone based on 2,2-dimethylolpropionic acid

[1329] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas outlet tube, 48.88 g (0.0567 mol) of the [(ricinoleic acid)2-oleic acid]acyl chloride from Synthesis Example 3 was mixed with 3.80 g (0.0284 mol) of 2,2-dimethylolpropionic acid. The mixture was heated to 100 °C for 8 h. Volatile substances were removed under reduced pressure (80 °C / 1 h / 20 mmHg). 1 ¹H NMR spectroscopy confirmed the complete conversion of the OH group in 2,2-hydroxymethylpropionic acid.

[1330] A light brown, transparent oil with the following basic structure is obtained:

[1331]

[1332] in

[1333]

[1334] Synthesis Example 4a

[1335] Synthesis of dendritic bis-[(ricinoleic acid)2-oleic acid]lactone

[1336] In a 100 mL three-necked flask equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas outlet tube, 64.57 g (0.03617 mol) of the branched bis-[(ricinoleic acid)2-oleic acid]lactone of Synthesis Example 4, heated to 80 °C. 8.61 g (0.0723 mol) of SOCl2 was added over 10 minutes. The reaction was maintained for 4 h. Volatile substances were removed under reduced pressure (80 °C / 1 h / 20 mmHg). 1 ¹H NMR spectroscopy confirmed the complete conversion of the C(O)OH group to the C(O)Cl group. 2.42 g (0.01808 mol) of bis-2,2-hydroxymethylpropionic acid was added at 80 °C, and the reaction was maintained for another 5 h. Volatile substances were removed under reduced pressure (80 °C / 0.5 h / 20 mmHg). 1 The complete conversion of the terminal OH group in bis-2,2-hydroxymethylpropionic acid was determined by 1H NMR spectroscopy.

[1337] A viscous, light brown, transparent oil with a dendritic structure was obtained:

[1338]

[1339] in

[1340]

[1341] Synthesis Example 4b

[1342] Synthesis of branched bis-[(ricinoleic acid)2-stearic acid]lactone based on 2,2-dimethylolpropionic acid

[1343] In a 250 mL three-necked flask equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas outlet tube, 95.06 g (0.1124 mol) of [(ricinoleic acid)2-stearic acid]lactone from Synthesis Example 2a was heated to 80 °C. 33.8 g (0.28 mol) of SOCl2 was added over 10 minutes. The reaction was maintained for 4 h. Volatile substances were removed under reduced pressure (80 °C / 1 h / 20 mmHg). 1 1H NMR spectroscopy confirmed that the C(O)OH group was completely converted into the C(O)Cl group.

[1344] In a 250 mL three-necked flask equipped with a reflux condenser, thermometer, mechanical stirrer, dropping funnel, and gas outlet tube, 92.88 g (0.1075 mol) of 2-stearoyl chloride intermediate (ricinoleic acid) and 7.22 g (0.0538 mol) of 2,2-dimethylolpropionic acid were mixed at 80 °C and the reaction was maintained for an additional 5 h. Volatile substances were removed under reduced pressure (80 °C / 0.5 h / 20 mmHg). 1 ¹H NMR spectroscopy confirmed the complete conversion of the OH group in 2,2-dihydroxymethylpropionic acid.

[1345] A viscous, light brown, transparent oil with the following basic structure was obtained:

[1346]

[1347] in

[1348]

[1349] Synthesis Example 4c

[1350] Synthesis of branched bis-(ricinoleic acid–12-hydroxystearic acid-oleic acid) lactone based on 2,2-dimethylolpropionic acid

[1351] In a 250 ml three-necked flask equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas outlet tube, 102.95 g (0.1218 mol) of the (ricinoleic acid-12-hydroxystearic acid-oleic acid) lactone from Synthesis Example 2b was heated to 80 °C. 42.8 g (0.36 mol) of SOCl2 was added over 10 minutes. The reaction was maintained for 4 h. Volatile substances were removed under reduced pressure (80 °C / 1 h / 20 mmHg). 1 HNMR spectroscopy confirmed that the C(O)OH group was completely converted into the C(O)Cl group.

[1352] In a 250 ml three-necked flask equipped with a reflux condenser, thermometer, mechanical stirrer, dropping funnel, and gas outlet tube, 104.22 g (0.1206 mol) of bis-(ricinoleic acid-12-hydroxystearic acid-oleic acid) acyl chloride intermediate and 8.09 g (0.0603 mol) of bis-2,2-hydroxymethylpropionic acid were mixed at 80 °C and the reaction was maintained for an additional 5 h. Volatile substances were removed under reduced pressure (80 °C / 0.5 h / 20 mmHg). 1 HNMR spectroscopy confirmed the complete conversion of the OH group in 2,2-dihydroxymethylpropionic acid.

[1353] A viscous, light brown, transparent oil with the following basic structure was obtained:

[1354]

[1355] in

[1356]

[1357] Synthesis Example 4d

[1358] Synthesis of branched (12-hydroxystearic acid-ricinoleic acid-oleic acid) lactone based on 2,2-dimethylolpropionic acid

[1359] In a 250 mL three-necked flask equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas outlet tube, 98.05 g (0.116 mol) of the (12-hydroxystearic acid-ricinoleic acid-oleic acid) lactone from Synthesis Example 2c was heated to 80 °C. 30.08 g (0.25 mol) of SOCl2 was added over 10 minutes. The reaction was maintained for 4 h. Volatile substances were removed under reduced pressure (80 °C / 1 h / 20 mmHg). 1 1H NMR spectroscopy confirmed that the C(O)OH group was completely converted into the C(O)Cl group.

[1360] In a 250 ml three-necked flask equipped with a reflux condenser, thermometer, mechanical stirrer, dropping funnel, and gas outlet tube, 97.4 g (0.1127 mol) of the (12-hydroxystearic acid-ricinoleic acid-oleic acid) acyl chloride intermediate and 7.56 g (0.0564 mol) of 2,2-dimethylolpropionic acid were mixed at 80 °C and the reaction was maintained for a further 5 h. Volatile substances were removed under reduced pressure (80 °C / 0.5 h / 20 mmHg). 1 1H NMR spectroscopy confirmed the complete conversion of the OH group in the hydroxymethyl group.

[1361] A viscous, light brown, transparent oil with the following basic structure was obtained:

[1362]

[1363] in

[1364]

[1365] Synthesis Example 5

[1366] Synthesis of α-branched bis-[(ricinoleic acid)5-oleic acid]lactone based on 2,2-dimethylolpropionic acid

[1367] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas outlet tube, 29.53 g (0.0173 mol) of [(ricinoleic acid)5-oleic acid]acyl chloride from Synthesis Example 3 was mixed with 1.16 g (0.00866 mol) of 2,2-dimethylolpropionic acid. The mixture was heated to 105 °C for 5 h. Volatile substances were removed under reduced pressure (80 °C / 10 min / 20 mmHg). 1 ¹H NMR spectroscopy confirmed the complete conversion of the OH group in 2,2-dihydroxymethylpropionic acid.

[1368] A light brown, transparent oil with the following basic structure is obtained:

[1369]

[1370] in

[1371]

[1372] Synthesis Example 6

[1373] Synthesis of Chloroacetic Acid Derivatives Based on Glycerol Crosslactone

[1374] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, mechanical stirrer, dropping funnel, and gas outlet tube, 40 g (0.434 mol) of glycerol was placed at room temperature. While stirring, 49.05 g (0.434 mol) of chloroacetyl chloride was added over 45 minutes. During this addition, the temperature was raised to 83 °C. Subsequently, the temperature was raised to 120 °C for 2 hours. 1 The formation of chloroacetic acid ester was confirmed by 1H NMR spectroscopy.

[1375] 5.72 g (0.034 mol) of glycerol monochloroacetate was mixed with 39.50 g (0.068 mol) of [(ricinoleic acid)-1-oleic acid] acyl chloride from Synthesis Example 3 at room temperature. The mixture was heated to 100 °C for 8 h. Volatile substances were removed under reduced pressure (80 °C / 1 h / 20 mmHg). 1 ¹H NMR spectroscopy confirmed the complete conversion of the OH group and the formation of additional ester moieties.

[1376] A light brown, transparent oil with the following general structure was obtained:

[1377]

[1378] in

[1379]

[1380] Synthesis Example 7

[1381] Synthesis of Chloroacetic Acid Derivatives Based on Castor Oil Laminolidinium

[1382] 40 g (0.0428 mol) of castor oil was placed in a 100 ml three-necked flask at room temperature, equipped with a reflux condenser, thermometer, mechanical stirrer, dropping funnel, and gas outlet tube. While stirring, 4.84 g (0.0428 mol) of chloroacetyl chloride was added over 10 minutes. The temperature was raised to 34 °C during this addition. Subsequently, the temperature was raised to 80 °C for 3 hours. 1 The formation of chloroacetic acid ester was confirmed by 1H NMR spectroscopy.

[1383] 49.83 g (0.0856 mol) of [(ricinoleic acid)-1-oleic acid] acyl chloride from Synthesis Example 3 was added. The temperature was maintained at 80 °C for 8 h. Volatile substances were removed under reduced pressure (80 °C / 2 h / 20 mmHg). 1 ¹H NMR spectroscopy confirmed the complete conversion of the OH groups in castor oil molecules and the formation of additional ester moieties.

[1384] A light brown, transparent oil with the following general structure was obtained:

[1385]

[1386] in

[1387]

[1388] and among them

[1389]

[1390] Synthesis Example 7a

[1391] Synthesis of Chloroacetic Acid Derivatives Based on Castor Oil Laminolidinium

[1392] In a 250 ml three-necked flask equipped with a reflux condenser, thermometer, mechanical stirrer, dropping funnel, and gas outlet tube, 80 g (0.0857 mol) of castor oil was placed and heated to 60 °C. While stirring, 9.68 g (0.0857 mol) of chloroacetyl chloride was added over 10 minutes. The temperature was raised to 80 °C during this addition. The temperature was then maintained at 80 °C for another 1.5 hours. 1 The formation of chloroacetic acid ester was confirmed by 1H NMR spectroscopy.

[1393] 100 g (0.1714 mol) of [(ricinoleic acid)-1-stearic acid] acyl chloride from Synthesis Example 2a was added. The temperature was maintained at 80 °C for 4 h. Volatile substances were removed under reduced pressure (90 °C / 2 h / 20 mmHg). 1 1H NMR spectroscopy confirmed the complete conversion of the OH groups in castor oil molecules and the formation of additional ester moieties.

[1394] A light brown, waxy material with the following general structure was obtained:

[1395]

[1396] in

[1397]

[1398] and among them

[1399]

[1400] Example 1

[1401] Synthesis of the amine salt of the tertiary amino alcohol ester of [(ricinoleic acid)-2-oleic acid]lactone

[1402] In a 500 mL four-necked flask equipped with a reflux condenser, thermometer, mechanical stirrer, dropping funnel, and gas outlet tube, 300 mL of n-heptane was mixed with 49.69 g (0.0577 mol) of [(ricinoleic acid)2-oleic acid] acyl chloride from Synthesis Example 3 at room temperature. After 20 minutes, 5.95 g (0.0577 mol) of (CH3)2NCH2CH2CH2OH was added. The temperature was raised to 37 °C and maintained at this temperature for 30 minutes. The n-heptane was removed under reduced pressure (30 °C / 2 h / 20 mmHg). 1 ¹H NMR spectroscopy confirmed the transformation of the OH group and the formation of the ester in (CH₃)₂NCH₂CH₂CH₂OH.

[1403] A light brown wax with the following structure was obtained:

[1404]

[1405] in

[1406]

[1407] Example 2

[1408] Synthesis of the amine salt of the tertiary amino alcohol ester of [(ricinoleic acid)-5-oleic acid]lactone

[1409] In a 250 ml four-necked flask equipped with a reflux condenser, thermometer, mechanical stirrer, dropping funnel, and gas outlet tube, 40 ml of n-heptane was mixed with 49.19 g (0.0289 mol) of 5-oleoyl (ricinoleic acid) from Synthesis Example 3 at 40 °C. After 5 minutes, 2.89 g (0.0289 mol) of (CH3)2NCH2CH2CH2OH was added. The temperature was raised to 43 °C and maintained at this temperature for 1 h. The n-heptane was removed under reduced pressure (30 °C / 2 h / 20 mmHg). 1 ¹H NMR spectroscopy confirmed the transformation of the OH group and the formation of the ester in (CH₃)₂NCH₂CH₂CH₂OH.

[1410] A light brown wax with the following structure was obtained:

[1411]

[1412] in

[1413]

[1414] Example 3

[1415] Synthesis of the amine salt of the tertiary amino alcohol ester of branched bis-[(ricinoleic acid)2-oleic acid]lactone

[1416] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas outlet tube, 25 g (0.014 mol) of the α-branched bis-[(ricinoleic acid)2-oleic acid]lactone of Synthesis Example 4 was mixed with 11 g (0.092 mol) of SOCl2 at 50 °C. The mixture was heated to 80 °C for 2.5 h. Excess SOCl2 was then removed under reduced pressure (80 °C / 1 h / 20 mmHg). 1 The formation of acyl chloride was confirmed by HNMR spectroscopy.

[1417] 22.4 g (0.0124 mol) of the acyl chloride was transferred to a 250 mL four-necked flask equipped with a reflux condenser, thermometer, mechanical stirrer, and dropping funnel. After 5 minutes, 140 mL of n-heptane and 1.28 g (0.00825 mol) of (CH3)2NCH2CH2CH2OH were added. The temperature was raised to 28 °C and maintained for 1 h. The n-heptane was removed under reduced pressure (30 °C / 3 h / 20 mmHg). 1 ¹H NMR spectroscopy confirmed the transformation of the OH group and the formation of the ester in (CH₃)₂NCH₂CH₂CH₂OH.

[1418] A light brown wax with the following structure was obtained:

[1419]

[1420] in

[1421]

[1422] Example 3a

[1423] Synthesis of amine salts of tertiary amino alcohol esters of dendritic bis-[(ricinoleic acid)2-oleic acid]lactone

[1424] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas outlet tube, 25 g (0.014 mol) of the branched bis-[(ricinoleic acid)2-oleic acid]lactone of Synthesis Example 4a was mixed with 11 g (0.092 mol) SOCl2 at 50 °C. The mixture was heated to 80 °C for 2.5 h. Excess SOCl2 was then removed under reduced pressure (80 °C / 1 h / 20 mmHg). 1 The formation of acyl chloride was confirmed by HNMR spectroscopy.

[1425] 22.4 g (0.0124 mol) of the acyl chloride was transferred to a 250 mL four-necked flask equipped with a reflux condenser, thermometer, mechanical stirrer, and dropping funnel. Over a 5-minute period, 140 mL of n-heptane and 1.28 g (0.00825 mol) of (CH3)2NCH2CH2CH2OH were added. The temperature was raised to 28 °C and maintained for 1 h. The n-heptane was removed under reduced pressure (30 °C / 3 h / 20 mmHg). 1 ¹H NMR spectroscopy confirmed the transformation of the OH group and the formation of the ester in (CH₃)₂NCH₂CH₂CH₂OH.

[1426] A light brown wax with the following structure was obtained:

[1427]

[1428] in

[1429]

[1430] Example 3b

[1431] Synthesis of the amine salt of the tertiary amino alcohol ester of α-branched bis-[(ricinoleic acid)2-stearic acid]lactone

[1432] In a 250 ml three-necked flask equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas outlet tube, 77 g (0.0430 mol) of the α-branched bis-[(ricinoleic acid)2-stearic acid]lactone of Synthesis Example 4b was mixed with 34.5 g (0.29 mol) of SOCl2 at 50 °C. The mixture was heated to 80 °C for 2.5 h. Excess SOCl2 was then removed under reduced pressure (80 °C / 1 h / 20 mmHg). 1 The formation of acyl chloride was confirmed by 1H NMR spectroscopy.

[1433] 71.5 g (0.0396 mol) of the acyl chloride was transferred to a 500 mL four-necked flask equipped with a reflux condenser, thermometer, mechanical stirrer, and dropping funnel. After 5 minutes, 190 g of n-heptane and 4.09 g (0.0396 mol) of (CH3)2NCH2CH2CH2OH were added. The temperature was raised to 30 °C and maintained for 1 h. The n-heptane was removed under reduced pressure (30 °C / 3 h / 20 mmHg). 1 ¹H NMR spectroscopy confirmed the transformation of the OH group and the formation of the ester in (CH₃)₂NCH₂CH₂CH₂OH.

[1434] A light brown wax with the following structure was obtained:

[1435]

[1436] in

[1437]

[1438] Example 3c

[1439] Synthesis of the amine salt of the tertiary amino alcohol ester of α-branched bis-(ricinoleic acid–12-hydroxystearic acid-oleic acid)lactone

[1440] In a 250 ml three-necked flask equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas outlet tube, 89.4 g (0.05 mol) of the α-branched bis-(ricinoleic acid-12-hydroxystearic acid-oleic acid) lactone of Synthesis Example 4c was mixed with 40.4 g (0.34 mol) of SOCl2 at 50 °C. The mixture was heated to 80 °C for 2.5 h. Excess SOCl2 was then removed under reduced pressure (80 °C / 1 h / 20 mmHg). 1 The formation of acyl chloride was confirmed by 1H NMR spectroscopy.

[1441] 85.11 g (0.0471 mol) of the acyl chloride was transferred to a 500 mL four-necked flask equipped with a reflux condenser, thermometer, mechanical stirrer, and dropping funnel. After 5 minutes, 187 g of n-heptane and 4.86 g (0.0471 mol) of (CH3)2NCH2CH2CH2OH were added. The temperature was raised to 32 °C and maintained for 1 h. The n-heptane was removed under reduced pressure (30 °C / 3 h / 20 mmHg). 1 ¹H NMR spectroscopy confirmed the transformation of the OH group and the formation of the ester in (CH₃)₂NCH₂CH₂CH₂OH.

[1442] A light brown wax with the following structure was obtained:

[1443]

[1444] in

[1445]

[1446] Example 3d

[1447] Synthesis of the amine salt of the tertiary amino alcohol ester of α-branched bis-(12-hydroxystearic acid-ricinoleic acid-oleic acid)lactone

[1448] In a 250 ml three-necked flask equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas outlet tube, 78 g (0.0436 mol) of the α-branched bis-(12-hydroxystearic acid-ricinoleic acid-oleic acid) lactone from Synthesis Example 4d was mixed with 22.77 g (0.19 mol) of SOCl2 at 50 °C. The mixture was heated to 80 °C for 2.5 h. Excess SOCl2 was then removed under reduced pressure (80 °C / 1 h / 20 mmHg). 1 The formation of acyl chloride was confirmed by 1H NMR spectroscopy.

[1449] 76.15 g (0.0421 mol) of the acyl chloride was transferred to a 500 mL four-necked flask equipped with a reflux condenser, thermometer, mechanical stirrer, and dropping funnel. After 5 minutes, 200 g of n-heptane and 4.34 g (0.0421 mol) of (CH3)2NCH2CH2CH2OH were added. The temperature was raised to 28 °C and maintained for 1 h. The n-heptane was removed under reduced pressure (30 °C / 3 h / 20 mmHg). 1 ¹H NMR spectroscopy confirmed the transformation of the OH group and the formation of the ester.

[1450] A light brown wax with the following structure was obtained:

[1451]

[1452] in

[1453]

[1454] Example 4

[1455] Synthesis of the amine salt of the tertiary amino alcohol ester of α-branched bis-[(ricinoleic acid)5-oleic acid]lactone

[1456] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas outlet tube, 28.63 g (0.00825 mol) of the α-branched bis-[(ricinoleic acid)5-oleic acid]lactone of Synthesis Example 5 was mixed with 7.2 g (0.0605 mol) SOCl2 at room temperature. The mixture was heated to 80 °C for 2.5 h. Excess SOCl2 was then removed under reduced pressure (80 °C / 1 h / 20 mmHg). 1 The formation of the acyl chloride was confirmed by 1H NMR spectroscopy.

[1457] The temperature was adjusted to 45°C, and after 5 minutes, 40 ml of n-heptane and 0.85 g (0.00825 mol) of (CH3)2NCH2CH2CH2OH were added. This temperature was maintained for 1 hour. The n-heptane was removed under reduced pressure (30°C / 3 hours / 20 mmHg). 1 ¹H NMR spectroscopy confirmed the transformation of the OH group and the formation of the ester in (CH₃)₂NCH₂CH₂CH₂OH.

[1458] A light brown wax with the following structure was obtained:

[1459]

[1460] in

[1461]

[1462] Example 5 (not based on the present invention)

[1463] Synthesis of tertiary amino alcohol esters of [(ricinoleic acid)-2-oleic acid]lactone

[1464] The protocol outlined in Example 1 is repeated, except that n-heptane is not removed under reduced pressure.

[1465] Conversely, the n-heptane solution was transferred to a separatory funnel and mixed with an alkaline mixture containing 100 g deionized water, 30 g NaCl, and 10 g NaOH. After phase separation, the aqueous (bottom) phase was removed. A mixture containing 100 g deionized water and 30 g NaCl was added to the upper organic phase. After mixing and phase separation, the bottom deionized water / NaCl phase was removed. This process using the deionized water / NaCl mixture was repeated 5 times. Finally, the organic phase was dried three times with 30 g NaCl. The n-heptane was removed under reduced pressure (30 °C / 2 h / 20 mmHg). 1 The formation of tertiary amino alcohol esters was confirmed by 1H NMR spectroscopy.

[1466] A low-viscosity, light brown liquid with the following structure was obtained:

[1467]

[1468] in

[1469]

[1470] Example 6

[1471] Synthesis of quaternary ammonium compounds based on diglycidyl ethers using the amine salt of the tertiary amino alcohol ester of [(ricinoleic acid)2-oleic acid]lactone.

[1472] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 1.5 g (0.01093 mol epoxy groups; specific epoxy content 0.00729 mol epoxy groups / 1 g) of glycerol diglycidyl ether, 10.55 g (0.01093 mol) of amine salt from Example 1, 55 g of 2-propanol, and 0.14 g of deionized water were mixed at room temperature. The mixture was heated to 80 °C for 11 h. Afterward, volatiles were removed under reduced pressure (40 °C / 2 h / 20 mmHg). 1 1H NMR spectroscopy confirmed the complete transformation of the epoxy group.

[1473] A light brown, viscous oil with the following structure was obtained:

[1474]

[1475] in

[1476]

[1477] Example 7

[1478] Synthesis of quaternary ammonium compounds based on glycerol triglycidyl ethers using the amine salt of the tertiary amino alcohol ester of [(ricinoleic acid)2-oleic acid]lactone.

[1479] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 1.5 g (0.01004 mol epoxy groups; specific epoxy content 0.00669 mol epoxy groups / 1 g) of glycerol triglycidyl ether, 10.14 g (0.01004 mol) of the amine salt from Example 1, 50 g of 2-propanol, and 0.15 g of deionized water were mixed at room temperature. The mixture was heated to 80 °C for 16 h. Afterward, volatiles were removed under reduced pressure (40 °C / 2 h / 20 mmHg). 1 1H NMR spectroscopy confirmed the complete transformation of the epoxy group.

[1480] A light brown, viscous oil with the following structure was obtained:

[1481]

[1482] in

[1483]

[1484] Example 8

[1485] Synthesis of a quaternary ammonium dimethyl ether based on glycerol triglycidyl ether using the amine salt of the tertiary amino alcohol ester of [(ricinoleic acid)2-oleic acid]lactone.

[1486] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 1.62 g (0.01004 mol epoxy groups; specific epoxy content 0.00621 mol epoxy groups / 1 g) of diglycidyl triglycidyl ether, 10.14 g (0.01004 mol) of the amine salt from Example 1, 50 g of 2-propanol, and 0.15 g of deionized water were mixed at room temperature. The mixture was heated to 80 °C for 14 h. Afterward, volatiles were removed under reduced pressure (40 °C / 2 h / 20 mmHg). 1 1H NMR spectroscopy confirmed the complete transformation of the epoxy group.

[1487] A light brown, viscous oil with the following structure was obtained:

[1488]

[1489] in

[1490]

[1491] Example 9

[1492] Synthesis of quaternary ammonium compounds based on polyglycerol polyglycidyl ethers using the amine salt of the tertiary amino alcohol ester of [(ricinoleic acid)2-oleic acid]lactone.

[1493] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 1.68 g (0.01004 mol epoxy groups; specific epoxy content 0.00597 mol epoxy groups / 1 g) of polyglycerol polyglycidyl ether, 10.14 g (0.01004 mol) of the amine salt from Example 1, 50 g of 2-propanol, and 0.15 g of deionized water were mixed at room temperature. The mixture was heated to 80 °C for 12 h. Afterward, volatiles were removed under reduced pressure (40 °C / 2 h / 20 mmHg). 1 1H NMR spectroscopy confirmed the complete transformation of the epoxy group.

[1494] A light brown, viscous oil with the following general structure was obtained:

[1495]

[1496] in

[1497]

[1498] Example 10

[1499] Synthesis of quaternary ammonium compounds based on diglycidyl ethers using the amine salt of the tertiary amino alcohol ester of [(ricinoleic acid)5-oleic acid]lactone.

[1500] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 0.69 g (0.0045 mol epoxy groups; specific epoxy content 0.00729 mol epoxy groups / 1 g) of glycerol diglycidyl ether, 8.42 g (0.0045 mol) of the amine salt from Example 2, 50 g of 2-propanol, and 0.1 g of deionized water were mixed at room temperature. The mixture was heated to 80 °C for 14 h. Afterward, volatiles were removed under reduced pressure (40 °C / 2 h / 20 mmHg). 1 1H NMR spectroscopy confirmed the complete transformation of the epoxy group.

[1501] A light brown, viscous oil with the following structure was obtained:

[1502]

[1503] in

[1504]

[1505] Example 11

[1506] Synthesis of quaternary ammonium compounds based on diglycidyl ethers using the amine salt of the tertiary amino alcohol ester of α-branched bis-[(ricinoleic acid)2-oleic acid]lactone.

[1507] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 0.46 g (0.0031 mol epoxy groups; specific epoxy content 0.00729 mol epoxy groups / 1 g) of glycerol diglycidyl ether, 6.0 g (0.0031 mol) of the amine salt from Example 3, 50 g of 2-propanol, and 0.1 g of deionized water were mixed at room temperature. The mixture was heated to 80 °C for 11 h. Afterward, volatiles were removed under reduced pressure (40 °C / 2 h / 20 mmHg). 1 1H NMR spectroscopy confirmed the complete transformation of the epoxy group.

[1508] A light brown wax with the following general structure was obtained:

[1509]

[1510] in

[1511]

[1512] Example 11a

[1513] Synthesis of quaternary ammonium compounds based on diglycidyl ethers using the amine salt of the tertiary amino alcohol ester of α-branched bis-[(ricinoleic acid)2-stearic acid]lactone.

[1514] In a 250 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 2.98 g (0.02417 mol epoxy groups; specific epoxy content 0.00729 mol epoxy groups / 1 g) of glycerol diglycidyl ether, 45.3 g (0.02417 mol) of the amine salt from Example 3b, 200 g of 2-propanol, and 0.15 g of deionized water were mixed at room temperature. The mixture was heated to 80 °C for 9 h. Afterward, volatiles were removed under reduced pressure (40 °C / 2 h / 20 mmHg). 1 1H NMR spectroscopy confirmed the complete transformation of the epoxy group.

[1515] A light brown wax with the following structure was obtained:

[1516]

[1517] in

[1518]

[1519] Example 11b

[1520] Synthesis of quaternary ammonium compounds based on diglycidyl ethers using amine salts of α-branched bis-(ricinoleic acid–12-hydroxystearic acid-oleic acid) lactone tertiary amino alcohol esters.

[1521] In a 250 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 3.13 g (0.0228 mol epoxy groups; specific epoxy content 0.00729 mol epoxy groups / 1 g) of glycerol diglycidyl ether, 44.1 g (0.0228 mol) of the amine salt from Example 3c, 200 g of 2-propanol, and 0.15 g of deionized water were mixed at room temperature. The mixture was heated to 80 °C for 9 h. Afterward, volatiles were removed under reduced pressure (40 °C / 2 h / 20 mmHg). 1 1H NMR spectroscopy confirmed the complete transformation of the epoxy group.

[1522] A light brown wax with the following general structure was obtained:

[1523]

[1524] in

[1525]

[1526] Example 11c

[1527] Synthesis of quaternary ammonium compounds based on diglycidyl ethers using amine salts of α-branched bis-(12-hydroxystearic acid–ricinoleic acid–oleic acid)lactone tertiary amino alcohol esters.

[1528] In a 250 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 3.33 g (0.0243 mol epoxy groups; specific epoxy content 0.00729 mol epoxy groups / 1 g) of glycerol diglycidyl ether, 45.6 g (0.0243 mol) of the amine salt from Example 3d, 200 g of 2-propanol, and 0.15 g of deionized water were mixed at room temperature. The mixture was heated to 80 °C for 9 h. Afterward, volatiles were removed under reduced pressure (40 °C / 2 h / 20 mmHg). 1 1H NMR spectroscopy confirmed the complete transformation of the epoxy group.

[1529] A light brown wax with the following general structure was obtained:

[1530]

[1531] in

[1532]

[1533] Example 12

[1534] Synthesis of bisquaternary ammonium compounds based on diglyceride diglycidyl ethers using the amine salt of the tertiary amino alcohol ester of α-branched bis-[(ricinoleic acid)5-oleic acid]lactone.

[1535] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 0.286 g (0.00209 mol epoxy groups; specific epoxy content 0.00729 mol epoxy groups / 1 g) of glycerol diglycidyl ether, 7.5 g (0.00209 mol) of the amine salt from Example 4, 50 g of 2-propanol, and 0.1 g of deionized water were mixed at room temperature. The mixture was heated to 80 °C for 11 h. Afterward, volatiles were removed under reduced pressure (40 °C / 2 h / 20 mmHg). 1 1H NMR spectroscopy confirmed the complete transformation of the epoxy group.

[1536] A light brown wax with the following general structure was obtained:

[1537]

[1538] in

[1539]

[1540] Example 13

[1541] Using the tertiary amino alcohol ester of [(ricinoleic acid)2-oleic acid]lactone, a quaternary ammonium diglyceride-based ether was synthesized with the same laminolide counterion.

[1542] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 1.0 g (0.00729 mol epoxy groups; epoxy content 0.00729 mol epoxy groups / 1 g) of glycerol diglycidyl ether, 6.77 g (0.00729 mol) of the tertiary amine from Example 5, 6.15 g (0.00729 mol) of [(ricinoleic acid) 2-oleic acid] from Synthetic Example 2, 50 g of 2-propanol, and 0.15 g of deionized water were mixed at room temperature. The mixture was heated to 80 °C for 11 h. Afterward, volatiles were removed under reduced pressure (40 °C / 2 h / 20 mmHg). 1 1H NMR spectroscopy confirmed the complete transformation of the epoxy group.

[1543] A light brown, viscous oil with the following general structure was obtained:

[1544]

[1545] in

[1546]

[1547] and among them

[1548]

[1549] Example 14

[1550] Using the tertiary amino alcohol ester of [(ricinoleic acid) 2-oleic acid] lactone, tri(quaternary ammonium) based on glycerol triglycidyl ether was synthesized with the same lactone as the counter ion.

[1551] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 1.0 g (0.00669 mol epoxy groups; epoxy content 0.00669 mol epoxy groups / 1 g) of glycerol triglycidyl ether, 6.21 g (0.00669 mol) of the tertiary amine from Example 5, 5.64 g (0.00669 mol) of [(ricinoleic acid) 2-oleic acid] from Synthesis Example 2, 50 g of 2-propanol, and 0.15 g of deionized water were mixed at room temperature. The mixture was heated to 80 °C for 16 h. Afterward, volatiles were removed under reduced pressure (40 °C / 1 h / 20 mmHg). 1 1H NMR spectroscopy confirmed the complete transformation of the epoxy group.

[1552] A light brown, viscous oil with the following structure was obtained:

[1553]

[1554] in

[1555]

[1556] and among them

[1557]

[1558] Example 15

[1559] Synthesis of tri(quaternary ammonium) based on diglycerol triglycidyl ether using tertiary amino alcohol esters of [(ricinoleic acid)2-oleic acid]lactone.

[1560] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 1.08 g (0.00669 mol epoxy groups; specific epoxy content 0.00621 mol epoxy groups / 1 g) of diglycerol triglycidyl ether, 6.21 g (0.00669 mol) of the tertiary amine from Example 5, 5.64 g (0.00669 mol) of [(ricinoleic acid) 2-oleic acid] from Synthetic Example 2, 50 g of 2-propanol, and 0.15 g of deionized water were mixed at room temperature. The mixture was heated to 80 °C for 14 h. Afterward, volatiles were removed under reduced pressure (40 °C / 1 h / 20 mmHg). 1 1H NMR spectroscopy confirmed the complete transformation of the epoxy group.

[1561] A light brown, viscous oil with the following structure was obtained:

[1562]

[1563] in

[1564]

[1565] and among them

[1566]

[1567] Example 16

[1568] Synthesis of quaternary ammonium compounds based on polyglycerol polyglycidyl ethers using tertiary amino alcohol esters of [(ricinoleic acid)2-oleic acid]lactone.

[1569] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 1.12 g (0.00669 mol epoxy groups; specific epoxy content 0.00597 mol epoxy groups / 1 g) of polyglycerol polyglycidyl ether, 6.21 g (0.00669 mol) of the tertiary amine from Example 5, 5.64 g (0.00669 mol) of [(ricinoleic acid) 2-oleic acid] from Synthesis Example 2, 50 g of 2-propanol, and 0.15 g of deionized water were mixed at room temperature. The mixture was heated to 80 °C for 13 h. Afterward, volatiles were removed under reduced pressure (40 °C / 1 h / 20 mmHg). 1 1H NMR spectroscopy confirmed the complete transformation of the epoxy group.

[1570] A light brown, viscous oil with the following general structure was obtained:

[1571]

[1572] in

[1573]

[1574] and among them

[1575]

[1576] Example 17

[1577] Synthesis of diethylene glycol-based quaternary ammonium compounds using tertiary amino alcohol esters of [(ricinoleic acid)2-oleic acid]lactone from Example 5.

[1578] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 9.285 g (0.01 mol) of the tertiary amine from Example 5, 1.295 g (0.01 mol) of diethylene glycol bis-(chloroacetic acid) ester, and 40 g of 2-propanol were mixed at room temperature. The mixture was heated to 80 °C for 12 h. Afterward, volatiles were removed under reduced pressure (40 °C / 2 h / 20 mmHg). 1 1H NMR spectroscopy confirmed the complete conversion of the CH2Cl group.

[1579] A light brown, viscous wax with the following general structure was obtained:

[1580]

[1581] in

[1582] And R2=-CH2CH2OCH2CH2-.

[1583] Example 18

[1584] Synthesis of quaternary ammonium salts based on 1,4-butanediol from the tertiary amino alcohol ester of [(ricinoleic acid)2-oleic acid]lactone of Example 1.

[1585] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 0.6 g (0.00593 mol) of 1,4-butanediol diglycidyl ether, 5.72 g (0.00593 mol) of the amine salt from Example 1, 55 g of 2-propanol, and 0.1 g of deionized water were mixed at room temperature. The mixture was heated to 80 °C for 11 h. Afterward, volatiles were removed under reduced pressure (40 °C / 2 h / 20 mmHg). 1 1H NMR spectroscopy confirmed the complete transformation of the epoxy group.

[1586] A light brown, oily liquid with the following general structure was obtained:

[1587]

[1588] in

[1589]

[1590] And where R2=-CH2CH2CH2CH2-

[1591] Example 19

[1592] Synthesis of quaternary ammonium compounds based on 1,4-butanediol–succinate from the amine salt of the tertiary amino alcohol ester of [(ricinoleic acid)2-oleic acid]lactone.

[1593] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 1.2 g (0.01186 mol epoxy group) of 1,4-butanediol diglycidyl ether, 0.35 g (0.00593 mol COOH) of succinic acid, 55 g of 2-propanol, and 0.03 g of trimethylamine were mixed at room temperature (to form R2). The mixture was heated to 80 °C for 15 h. 1 H NMR spectroscopy confirmed the partial transformation of epoxy groups.

[1594] Then, 5.72 g (0.00593 mol) of the amine salt from Example 1 was added and the reaction was continued at 80 °C for 10 h. Volatile substances were removed under reduced pressure (40 °C / 2 h / 20 mmHg). 1 1H NMR spectroscopy confirmed the complete transformation of the epoxy group.

[1595] A light brown, highly viscous liquid with the following structure was obtained:

[1596]

[1597] in

[1598]

[1599] and among them

[1600]

[1601] Example 20

[1602] Synthesis of di-quaternary ammonium based on glycerol lactone

[1603] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 25 g (0.0198 mol) of a chloroacetic acid derivative based on a glycerol lactone from Synthetic Example 6, 1.71 g (0.0099 mol) of N,N,N',N'-tetramethyl-1,6-hexanediamine, and 50 g of 2-propanol were mixed at room temperature. The mixture was heated to 80 °C for 7 h. Volatile substances were removed under reduced pressure (40 °C / 2 h / 20 mmHg). 1 1H NMR spectroscopy confirmed the complete conversion of the CH2Cl group.

[1604] A light brown, oily liquid with the following general structure was obtained:

[1605]

[1606] in

[1607]

[1608] Example 21

[1609] Synthesis of N-terminated ricin lactone-based di-quaternary ammonium compounds

[1610] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 25 g (0.0119 mol CH2Cl groups) of a castor oil-based lactone chloroacetic acid derivative from Synthetic Example 7, 1.03 g (0.006 mol) of N,N,N',N'-tetramethyl-1,6-hexanediamine, and 60 g of 2-propanol were mixed at room temperature. The mixture was heated to 80 °C for 15 h. Volatile substances were removed under reduced pressure (40 °C / 2 h / 20 mmHg). 1 1H NMR spectroscopy confirmed the complete conversion of the CH2Cl group.

[1611] A light brown, oily liquid with the following structure was obtained:

[1612]

[1613] in

[1614]

[1615] and among them

[1616]

[1617] Example 22

[1618] Synthesis of N-terminated branched ricin lactone-based quaternary ammonium compounds

[1619] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 0.22 g (0.0016 mol epoxy groups; specific epoxy content 0.00729 mol epoxy groups / 1 g) of glycerol diglycidyl ether, 0.30 g (0.0016 mol NH groups) of (CH3)2NCH2CH2CH2NHCH2CH2CH2N(CH3)2, and 55 g of 2-propanol were mixed at room temperature. The mixture was heated to 80 °C for 8 h. 1 1H NMR spectroscopy confirmed the complete transformation of the epoxy group.

[1620] 6.73 g (0.0032 mol CH2Cl groups) of the castor oil-based lactone chloroacetate derivative from Synthetic Example 7 was added, and the reaction was continued at 80 °C for 10 h. Volatile substances were removed under reduced pressure (40 °C / 2 h / 20 mmHg).

[1621] pass 1 The conversion rate of the CH2Cl group, as determined by 1H NMR spectroscopy, was 97%.

[1622] A light brown, oily liquid with the following general structure was obtained:

[1623]

[1624] in

[1625]

[1626] and among them

[1627] Example 23

[1628] Based on N + N + Synthesis of diquaternary ammonium compounds derived from sugar-modified castor oil lactone

[1629] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 0.44 g (0.0032 mol epoxy groups; specific epoxy content 0.00729 mol epoxy groups / 1 g) of glyceryl diglycidyl ether, 0.62 g (0.0032 mol) of N-methylglucosamine, and 66 g of 1,3-propanediol were mixed at room temperature. The mixture was heated to 80 °C for 8.5 h. 1 1H NMR spectroscopy confirmed the complete transformation of the epoxy group.

[1630] 6.73 g (0.0032 mol CH2Cl groups) of the castor oil-based lactone chloroacetate derivative from Synthesis Example 7 was added and the reaction was continued at 80 °C for 13 h.

[1631] pass 1 The conversion rate of the CH2Cl group was confirmed by 1H NMR spectroscopy.

[1632] A pale yellow oily liquid containing quaternary ammonium compounds with the following general structure was obtained:

[1633]

[1634] in

[1635]

[1636] and among them

[1637]

[1638] Example 24

[1639] Synthesis of castor oil lactone-based derivatives with a pendant quaternary ammonium moiety

[1640] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 0.44 g (0.0032 mol epoxy groups; specific epoxy content 0.00729 mol epoxy groups / 1 g) of glycerol diglycidyl ether, 0.163 g (0.0016 mol) of N,N-dimethyl-1,3-propanediamine, and 55 g of 2-propanol were mixed at room temperature. The mixture was heated to 80 °C for 8.5 h. 1 1H NMR spectroscopy confirmed the complete transformation of the epoxy group.

[1641] 3.36 g (0.0016 mol CH2Cl groups) of a castor oil-based lactone chloroacetate derivative from Synthetic Example 7 was added, and the reaction was continued at 80 °C for 13 h. Volatile matter was removed under reduced pressure (40 °C / 2 h / 20 mmHg). 1 The conversion rate of the CH2Cl group was confirmed by 1H NMR spectroscopy.

[1642] A pale yellow oily liquid containing quaternary ammonium compounds with the following general structure was obtained:

[1643]

[1644] in

[1645]

[1646] and among them

[1647]

[1648] The number of repeating units n in the above-shown structural formula of the compound obtained through the above procedure is in the range of n≤30.

[1649] Example 25

[1650] Synthesis of Quaternary Ammonium Derivatives Based on Polyglycerol-Polyricinoleate (PGPR)

[1651] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, mechanical stirrer, dropping funnel, and gas outlet tube, 60 g (0.0964 mol OH groups; OH content 0.00161 mol OH groups / 1 g material) of commercially available polyglycerol-polyricinoleate was placed at 31 °C. While stirring, 8.45 g (0.0748 mol) of chloroacetyl chloride was added over 30 minutes. The temperature was raised to 39 °C. The mixture was heated to 70 °C and held at this temperature for 3 h. Afterward, volatiles were removed under reduced pressure (40 °C / 1 h / 20 mmHg). 1 The formation of the chloroacetic acid ester structure was confirmed by HNMR spectroscopy.

[1652] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 27 g (0.0307 mol CH₂Cl) of the above-mentioned PGPR-chloroacetic acid derivative, 2.64 g (0.0153 mol) of N,N,N',N'-tetramethyl-1,6-hexanediamine, and 40 g of 2-propanol were mixed at room temperature and heated to 80 °C for 6 h. Volatile substances were removed under reduced pressure (40 °C / 2 h / 20 mmHg). 1 The conversion rate of the CH2Cl group was confirmed by 1H NMR spectroscopy.

[1653] A pale yellow wax was obtained.

[1654] Example 26

[1655] Synthesis of Quaternary Ammonium Derivatives Based on Polyglycerol-Polyricinoleate (PGPR)

[1656] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, mechanical stirrer, dropping funnel, and gas outlet tube, 60 g (0.0964 mol OH groups; OH content 0.00161 mol OH groups / 1 g material) of commercially available polyglycerol-polyricinoleate was placed at 24 °C. While stirring, 4.83 g (0.0427 mol) of chloroacetyl chloride was added over 30 minutes. The temperature was raised to 28 °C. The mixture was heated to 70 °C and held at this temperature for 3 h. Afterward, volatiles were removed under reduced pressure (40 °C / 1.5 h / 20 mmHg). 1 The formation of the chloroacetic acid ester structure was confirmed by HNMR spectroscopy.

[1657] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 27 g (0.0193 mol CH₂Cl) of the above-mentioned PGPR-chloroacetic acid derivative, 1.66 g (0.00962 mol) of N,N,N',N'-tetramethyl-1,6-hexanediamine, and 40 g of 2-propanol were mixed at room temperature and heated to 80 °C for 8 h. Volatile substances were removed under reduced pressure (40 °C / 1 h / 20 mmHg). 1 The conversion rate of the CH2Cl group was confirmed by 1H NMR spectroscopy.

[1658] A light brown wax was obtained.

[1659] Example 27

[1660] Synthesis of polyquaternary ammonium salts having a crosslactone moiety linked to a glycerol unit

[1661] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 2.71 g (0.0197 mol epoxy groups; specific epoxy content 0.00729 mol epoxy groups / 1 g) of glyceryl diglycidyl ether, 1.87 g (0.0197 mol) of chloroacetic acid, 0.2 g of triethylamine, and 63.4 g of methoxypropyl acetate were mixed at room temperature. The mixture was heated to 100 °C for 8 hours. 1 1H NMR spectroscopy confirmed the complete transformation of the epoxy group.

[1662] The mixture was cooled to room temperature and 11.48 g (0.0197 mol) of [(ricinoleic acid)-1-oleic acid] acyl chloride, used as an intermediate in Synthesis Example 3, was added after 15 minutes. The temperature was then raised to 100°C and maintained for 7 hours. 1 The transformation of the C(O)Cl group was confirmed by 1H NMR spectroscopy.

[1663] 3.4 g (0.0197 mol) of N,N,N',N'-tetramethyl-1,6-hexanediamine was added, and the reaction was continued at 100 °C for 7 h.1 The transformation of the CH2Cl group was confirmed by 1H NMR spectroscopy. Volatile substances were removed under reduced pressure (80℃ / 5h / 20mmHg).

[1664] A light brown wax with the following general structure was obtained:

[1665]

[1666] in

[1667]

[1668] The number of repeating units n in the above-shown structural formula of the compound obtained through the above procedure is in the range of n≤30.

[1669] Example 28

[1670] Have connections to each N + Synthesis of di-quaternary ammonium compounds from the lactone moiety of group-bonded glycerol units

[1671] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 10.5 g (0.0765 mol epoxy groups; specific epoxy content 0.00729 mol epoxy groups / 1 g) of glycerol diglycidyl ether, 43.09 g (0.0765 mol) of (ricinoleic acid-oleic acid) from Synthetic Example 1, 0.56 g (0.0066 mol) of N,N,N',N'-tetramethyl-1,6-hexanediamine, and 24.3 g of propylene glycol monomethyl ether were mixed at room temperature. The mixture was heated to 100 °C for 15 h. 1 1H NMR spectroscopy confirmed the complete transformation of the epoxy group.

[1672] The solvent was removed under reduced pressure (70℃ / 4h / 20mmHg). Then, 2.67 g (0.0236 mol) of chloroacetyl chloride was added. The temperature was increased to 48℃. Volatile substances were removed under reduced pressure (40℃ / 1h / 20mmHg).

[1673] Add 2.03 g (0.0118 mol) of N,N,N',N'-tetramethyl-1,6-hexanediamine and 24.3 g of propylene glycol monomethyl ether and heat the mixture to 100 °C for 13 h.

[1674] Volatile substances were removed under reduced pressure (80℃ / 5h / 20mmHg). (By...) 1 The transformation of the CH2Cl group was confirmed by 1H NMR spectroscopy.

[1675] A light brown wax with the following general structure was obtained:

[1676]

[1677] in

[1678]

[1679] and among them

[1680]

[1681] Synthesis Example 29a

[1682] Synthesis of [(ricinoleic acid)6-succinic acid–(ricinoleic acid)6]diacid lactone

[1683] Two 250ml three-necked flasks, A and B, equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas outlet tube, were rinsed with nitrogen.

[1684] Bottle A is used to react the starting materials dicarboxylic acid chloride, succinyl dichloride, or fatty acyl chloride with castor oil acid to produce chain-extended fatty ester acids. The subsequent addition of SOCl2 produces the corresponding fatty ester acyl chlorides.

[1685] Bottle B is used to react the formed fatty ester acyl chloride with ricinoleic acid to produce a chain-extended fatty ester acid. The subsequent addition of SOCl2 produces the corresponding fatty ester acyl chloride. This fatty acyl chloride is transferred back to bottle A and reacted with fresh ricinoleic acid. The above cycle is repeated until the lactone [(ricinoleic acid)6-succinic acid-(ricinoleic acid)6] is prepared.

[1686] The general procedure for the synthesis of chain-extended fatty acid esters:

[1687] The calculated amount of ricinoleic acid was placed in a flask. An equimolar amount of fatty acid ester chloride was slowly added at room temperature. To complete the reaction, the temperature was raised to 80°C for 3 hours. 1 1H NMR spectroscopy confirmed complete conversion of the OH group.

[1688] The general procedure for the synthesis of fatty acid ester chlorides:

[1689] The calculated amount of fatty acid esters was placed in a flask. SOCl2 (three times excess) was slowly added at room temperature. The mixture was then heated to 80°C and maintained at this temperature for 3 hours. Afterward, excess SOCl2 was removed under reduced pressure (80°C / 2 hours / 20 mmHg). 1 1H NMR spectroscopy confirmed that the C(O)OH group was completely converted into the C(O)Cl group.

[1690] The table below summarizes the materials and quantities used.

[1691]

[1692]

[1693] Note: When referring to the castor oil group, the term "rici" is used instead of the term "ricinoleic acid", and when referring to the succinyl group, the term "succ" is used instead of the term "succinic acid".

[1694] A light brown, transparent oil with the following structure [(rici)6-succinyl-(rici)6] was obtained:

[1695]

[1696] Example 29b

[1697] Synthesis of di-quaternary ammonium compounds based on tertiary amino alcohol esters of [(ricinoleic acid)6-succinic acid–(ricinoleic acid)6]diacid lactone

[1698] In a 250 ml three-necked flask equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas outlet tube, 59.57 g (0.0171 mol) of the synthetic example 29a [(ricinoleic acid)6-succinic acid–(ricinoleic acid)6]diacid lactone was mixed with 15.64 g (0.131 mol) of SOCl2 at 60 °C. The mixture was heated to 80 °C for 3.5 h. Excess SOCl2 was then removed under reduced pressure (80 °C / 1 h / 20 mmHg). 1 The formation of the corresponding acyl chloride was confirmed by 1H NMR spectroscopy.

[1699] After cooling to room temperature, 140 g of n-heptane and 3.5 g (0.0342 mol) of (CH3)2NCH2CH2CH2OH were added over 5 minutes. The temperature was increased from 24 °C to 31 °C and maintained for 4 h. The n-heptane was removed under reduced pressure (30 °C / 3 h / 20 mmHg). 1 ¹H NMR spectroscopy confirmed the transformation of the OH group and the formation of the ester.

[1700] A light brown wax with the following structure was obtained:

[1701]

[1702] Example 29c

[1703] Synthesis of glycerol-based quaternary ammonium compounds using the amine salt of the tertiary amino alcohol ester of [(ricinoleic acid)6-succinic acid–(ricinoleic acid)6]diacid lactone.

[1704] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 0.75 g (0.00549 mol epoxy groups; specific epoxy content 0.00729 mol epoxy groups / 1 g) of glycerol diglycidyl ether, 10.23 g (0.00275 mol) of the amine salt from Synthesis Example 29b, 50 g of 2-propanol, and 0.1 g of deionized water were mixed at room temperature. The mixture was heated to 80 °C for 8 h. Afterward, volatiles were removed under reduced pressure (40 °C / 2 h / 20 mmHg). 1 1H NMR spectroscopy confirmed the complete transformation of the epoxy group.

[1705] A light brown wax with the following general structure was obtained:

[1706] The quaternary ammonium has -[AB] n -Structure, in which

[1707]

[1708] and

[1709]

[1710] The structural formula of the compound obtained through the above procedure is [AB]. n The number of repeating units n in - is in the range of n≤30.

[1711] Application Trial

[1712] Combing force measurement

[1713] Combing force measurements were performed to quantify the effects of the compounds according to the invention. A Miniature Tensile Tester 175 (Dia-Stron Limited) was used.

[1714] Two different types of hair (Kerling International) were selected for these measurements:

[1715] Hair styling method 1 (buffalo hair)

[1716] The weight of the hairline to be treated was determined, and the total amount of active ingredient (based on the target mg active ingredient / 1g buffalo hair) was dissolved in 2-propanol. The amount of 2-propanol used was calculated using the following formula:

[1717] m 2-丙醇 (g) = 1.94xm 整理的头发

[1718] The 2-propanol solution was evenly distributed over the hairline. The hairline was then air-dried for 2 hours and further processed as outlined in the general protocol.

[1719] Hair styling method 2 (for damaged hair)

[1720] The weight of the hairline to be treated was determined, and the total amount of active ingredient (based on the target mg active ingredient / 1g buffalo hair) was dissolved in 2-propanol. The amount of 2-propanol used was calculated using the following formula:

[1721] m 2-丙醇 (g)=0.64xm 整理的头发

[1722] The 2-propanol solution was evenly distributed over the hairline. The hairline was then air-dried for 2 hours and further processed as outlined in the general protocol.

[1723] General protocols for the pretreatment and handling of hair locks

[1724] Each hair strand (2.5 cm) was cut from the corresponding reserve hair strands and equilibrated in a humidity chamber at 50% relative humidity for 12 hours. Afterwards, the dry tear force and wet average force were measured for the untreated hair strands (the hair strands were rinsed with 38°C tap water for 30 seconds) (baseline measurement results). Three strokes were performed. The force data from the third stroke was used for calculations.

[1725] The hair strands were air-dried and equilibrated in a climate chamber for another 15 hours. Afterward, they were treated with a 2-propanol solution as described in methods 1 and 2 for hair styling, air-dried for 2 hours, and equilibrated in a climate chamber for another 15 hours. Finally, the dry tearing force and wet average force were measured on the treated hair strands (the hair strands were rinsed with 38°C tap water for 30 seconds) (measurement results for the treated hair). Three passes were performed. The force data from the third pass was used for calculation.

[1726] The ratio between the combing force required before styling (baseline measurement) and the combing force after styling (measurement of styled hair) describes the effectiveness of the conditioner.

[1727] The reduction in relative combing force is calculated using the following formula:

[1728] Decrease in force (%) = (force) 基线 -force 经整理 )x100 / force 基线

[1729] Results of combing force measurement

[1730] buffalo hair

[1731]

[1732]

[1733] Damaged hair

[1734]

[1735] The data in the two tables above regarding buffalo hair and damaged human hair show that the compounds according to the present invention can reduce combing forces on different keratin matrices.

[1736] The comparison of data for compounds 6, 17, and 21 regarding buffalo hair and damaged human hair highlights the specific effectiveness of the compounds of the present invention on human hair.

[1737] Data from compounds 11a, 11b, and 11c demonstrate that a mixed polyfatty acid sequence consisting of saturated and unsaturated fatty acids is effective for human hair.

[1738] Data from compound 29c show that, in addition to the monofunctional polyfatty acid moiety terminated by monofunctional fatty acids (i.e., oleic acid and stearic acid), difunctional and higher-functional (i.e., polyfatty acid moieties located within the polymer chain) polyfatty acid moieties are also effective for human hair.

[1739] Synthesis Example 30

[1740] Synthesis of di-quaternary ammonium compounds using castor oil-based chloroacetic acid derivatives of lactones.

[1741] 117.77 g (0.1262 mol) of castor oil was placed in a 500 ml three-necked flask at room temperature, equipped with a reflux condenser, thermometer, mechanical stirrer, dropping funnel, and gas outlet tube. While stirring, 14.25 g (0.1262 mol) of chloroacetyl chloride was added over 10 minutes. The temperature was raised to 34 °C during this addition. Subsequently, the temperature was raised to 80 °C for 1 hour. 1 The formation of chloroacetic acid ester was confirmed by 1H NMR spectroscopy.

[1742] 75.93 g (0.2523 mol) of oleoyl chloride was added over a 20-minute period. The temperature was then maintained at 80 °C for 2 hours. Volatile substances were removed under reduced pressure (80 °C / 2 h / 20 mmHg). 1 1H NMR spectroscopy confirmed the complete conversion of the OH groups in castor oil molecules and the formation of additional ester moieties.

[1743] A light brown, transparent oil with the following general structure was obtained:

[1744]

[1745] in

[1746]

[1747] and among them

[1748]

[1749] Add 185 g of 2-propanol and 10.87 g of N,N,N',N'-tetramethyl-1,6-hexanediamine (0.0631 mol) and heat the mixture to 80 °C for 27 hours.

[1750] pass 1 1H NMR spectroscopy confirmed the complete conversion of the CH2Cl group.

[1751] A light brown liquid containing di-quaternary ammonium with the following structure was obtained:

[1752]

[1753] in

[1754]

[1755] and among them

[1756]

[1757] Synthesis Example 30a

[1758] Synthesis of di-quaternary ammonium compounds using castor oil-based lactone chloroacetate derivatives and possessing oleate counterions.

[1759] In a 500ml beaker equipped with a magnetic stirrer, 100g (0.000323mol Cl) was added. - The solution from Example 30 (1 g solution), 9.85 g sodium oleate (0.0323 mol), and 5.5 g DI water were mixed for 1 h.

[1760] Prepare a second mixture with the same composition.

[1761] Combine the two mixtures and remove the volatiles (40°C / 20 mbar / 4 hours).

[1762] A light brown viscous material with the following structure was obtained:

[1763]

[1764] in

[1765]

[1766] It has two anionic counterions

[1767]

[1768] and among them

[1769]

[1770] The sodium chloride formed precipitates (extracts) during storage.

[1771] Synthesis Example 30b

[1772] Synthesis of di-quaternary ammonium compounds using castor oil-based lactone chloroacetate derivatives and possessing counterions based on ricinoleic acid–oleic acid dimers.

[1773] In a 500ml beaker equipped with a magnetic stirrer, 100g (0.000323mol Cl) was added. - The solution of Example 30 (1 g solution), 18.19 g (0.0323 mol) of castor oleic acid-oleic acid dimer from Synthesis Example 1, 5.5 g DI water and 1.16 g NaOH were mixed for 1 h.

[1774] Prepare a second mixture with the same composition.

[1775] Combine the two mixtures and remove the volatiles (40°C / 20 mbar / 4 hours).

[1776] A light brown viscous material with the following structure was obtained:

[1777]

[1778] in

[1779]

[1780] It has two anionic counterions

[1781]

[1782] and among them

[1783]

[1784] The sodium chloride formed precipitates during storage.

[1785] Example 31

[1786] Synthesis of hexa-tertiary amines

[1787] In a 1000 ml three-necked flask equipped with a reflux condenser, thermometer, magnetic stirrer, and N2 inlet / outlet, 22.89 g (0.1669 mol epoxy groups; specific epoxy content 0.00729 mol epoxy groups / 1 g) of glycerol diglycidyl ether, 31.26 g (0.1669 mol NH groups) of (CH3)2NCH2CH2CH2NHCH2CH2CH2N(CH3)2, and 450 g of propylene glycol monomethyl ether were mixed at room temperature. The mixture was heated to 110 °C for 8 hours. 1 1H NMR spectroscopy confirmed the complete transformation of the epoxy group.

[1788] A light brown solution containing 10.74% active ingredient at 0.99299 mmol amine / 1g solution was obtained.

[1789] The approximate structure of hexa-tertiary amines:

[1790]

[1791] Example 31a

[1792] Synthesis of hexa-tertiary amines

[1793] In a 500 ml three-necked flask equipped with a reflux condenser, thermometer, magnetic stirrer, and N2 inlet / outlet, 11.83 g (0.1169 mol epoxy groups) of 1,4-butanediol diglycidyl ether, 21.91 g (0.1169 mol NH groups) of (CH3)2NCH2CH2CH2NHCH2CH2CH2N(CH3)2, and 221.87 g of propylene glycol monomethyl ether were mixed at room temperature. The mixture was heated to 115 °C for 10 hours. 1 1H NMR spectroscopy confirmed the complete transformation of the epoxy group.

[1794] A pale yellow solution containing 1.3815 mmol amine / 1g solution was obtained.

[1795] The approximate structure of hexa-tertiary amines:

[1796]

[1797] Synthesis Example 32

[1798] Synthesis of tetra-quaternary ammonium compounds using castor oil-based chloroacetic acid derivatives of lactones.

[1799] In a 1000 ml three-necked flask equipped with a reflux condenser, thermometer, mechanical stirrer, and N2 inlet / outlet, 216 g of the solution from Example 31, 220 g (0.143 mol) of the castor oil-based chloroacetic acid intermediate described in Example 30, and 55.2 g of propylene glycol monomethyl ether were mixed at room temperature. The temperature was raised to 115 °C for 25 hours. Afterward, volatiles were removed under reduced pressure (60 °C / 20 mbar / 4 hours).

[1800] A light brown, transparent, viscous oil with the following general structure was obtained:

[1801]

[1802] It has four anionic counterions Cl. -

[1803] in

[1804]

[1805] and among them

[1806]

[1807] Synthesis Example 32a

[1808] Synthesis of tetra-quaternary ammonium compounds using castor oil-based lauryl chloride ester derivatives and possessing ricinoleic acid-oleic acid dimer counterions.

[1809] In a 500 ml single-necked flask, place 100 g of tetra-quaternary ammonium from Example 32, 32.60 g (0.057906 mol COOH) of castor oil-oleic acid dimer from Synthesis Example 1, 2.08 g of NaOH, and 5.5 g of DI water. Mix the composition at atmospheric pressure for 2 hours on a rotary evaporator. Then, remove the volatiles at 40 °C / 20 mbar / 2 hours.

[1810] A light brown, viscous material with the following general structure was obtained:

[1811]

[1812] It has four anionic counterions

[1813]

[1814] in

[1815]

[1816] and among them

[1817]

[1818] The sodium chloride formed precipitates during storage.

[1819] Synthesis Example 32b

[1820] Synthesis of tetra-quaternary ammonium compounds using castor oil-based lactone chloroacetate derivatives and having additional amine salt groups.

[1821] In a 500 ml single-necked flask, 100.40 g of tetra-quaternary ammonium (0.02906 mol tertiary amine) from Example 32, 16.36 g (0.02906 mol COOH) of castor oil-oleic acid dimer from Synthesis Example 1, and 5.5 g of DI water were placed. The composition was mixed in a rotary evaporator at atmospheric pressure for 2 hours. Afterwards, volatiles were removed at 40 °C / 20 mbar / 2 hours.

[1822] A light brown, viscous material with the following general structure was obtained:

[1823]

[1824] It has four anionic counterions Cl. -

[1825] and two anionic counterions

[1826]

[1827] in

[1828]

[1829] and among them

[1830]

[1831] Example 33

[1832] Synthesis of di-quaternary ammonium compounds using castor oil-based chloroacetic acid derivatives of lactones.

[1833] In a 1000 ml three-necked flask equipped with a reflux condenser, thermometer, mechanical stirrer, and N2 inlet / outlet, 216 g of the solution from Example 31, 145.95 g (0.0695 mol) of the castor oil-based chloroacetic acid intermediate described in Synthesis Example 7, and 168 g of propylene glycol monomethyl ether were mixed at room temperature. The temperature was raised to 115 °C for 32 hours. Volatile substances were then removed under reduced pressure (60 °C / 20 mbar / 3 hours).

[1834] A light brown, transparent, viscous oil with the following general structure was obtained:

[1835]

[1836] It has two anionic counterions, Cl. -

[1837] in

[1838]

[1839] and among them

[1840]

[1841] Synthesis Example 33a

[1842] Synthesis of di-quaternary ammonium compounds using castor oil-based lactone chloroacetate derivatives and having two additional amine salt groups.

[1843] 86.36 g of di-quaternary ammonium from Example 33, 19.99 g (0.0355 mol COOH) of castor oil-oleic acid dimer from Synthesis Example 1, and 5.5 g of DI water were placed in a 500 ml single-necked flask. The composition was mixed at atmospheric pressure for 2 hours on a rotary evaporator. Volatile substances were then removed at 40 °C / 20 mbar / 2 hours.

[1844] A light brown, viscous material with the following general structure was obtained:

[1845]

[1846] It has two anionic counterions, Cl. - and

[1847] Two anionic counterions

[1848]

[1849] in

[1850]

[1851] and among them

[1852]

[1853] Synthesis Example 33b

[1854] Synthesis of di-quaternary ammonium compounds using castor oil-based lauryl chloride ester derivatives and having four additional amine salt groups.

[1855] 73.45 g of di-quaternary ammonium from Example 33, 34.01 g (0.0604 mol COOH) of castor oil-oleic acid dimer from Synthesis Example 1, and 4.04 g of DI water were placed in a 500 ml single-necked flask. The composition was mixed at atmospheric pressure for 2 hours on a rotary evaporator. Volatile substances were then removed at 40 °C / 20 mbar / 2 hours.

[1856] A light brown, viscous material with the following general structure was obtained:

[1857]

[1858] It has two anionic counterions, Cl. - and

[1859] Four anionic counterions

[1860]

[1861] in

[1862]

[1863] and among them

[1864]

[1865] Example 34

[1866] Synthesis of di-quaternary ammonium compounds using castor oil-based chloroacetic acid derivatives of lactones.

[1867] In a 1000 ml three-necked flask equipped with a reflux condenser, thermometer, mechanical stirrer, and N2 inlet / outlet, 217.19 g of the solution from Example 31a, 210 g (0.1 mol) of the castor oil-based chloroacetic acid intermediate described in Synthesis Example 7, and 50 g of propylene glycol monomethyl ether were mixed at room temperature. The temperature was raised to 115 °C for 34 hours. Volatile substances were then removed under reduced pressure (60 °C / 20 mbar / 4 hours).

[1868] A light brown, transparent, viscous oil with the following general structure was obtained:

[1869]

[1870] It has two anionic counterions, Cl. -

[1871] in

[1872]

[1873] and among them

[1874]

[1875] Synthesis Example 34a

[1876] Synthesis of tetra-quaternary ammonium compounds using castor oil-based lauryl chloride chloroacetate derivatives and having two additional oleate amine salt groups.

[1877] 116.13 g of di-quaternary ammonium from Example 34, 13.29 g (0.047 mol COOH) of oleic acid, and 6.39 g of DI water were placed in a 500 ml single-necked flask. The composition was mixed at atmospheric pressure on a rotary evaporator for 2 hours. Volatile substances were then removed at 40 °C / 20 mbar / 2 hours.

[1878] A light brown, viscous material with the following general structure was obtained:

[1879]

[1880] It has two anionic counterions, Cl. - ,and

[1881] Two anionic counterions

[1882]

[1883] in

[1884]

[1885] and among them

[1886]

[1887] Synthesis Example 34b

[1888] Synthesis of tetra-quaternary ammonium compounds using castor oil-based lauryl chloride ester derivatives and having two additional castor oil-oleic acid-oleic acid dimer amine salt groups.

[1889] 110.47 g of di-quaternary ammonium from Example 34, 25.19 g (0.0447 mol COOH) of castor oil-oleic acid dimer from Synthesis Example 1, and 6.08 g of DI water were placed in a 500 ml single-necked flask. The composition was mixed at atmospheric pressure for 2 hours on a rotary evaporator. Volatile substances were then removed at 40 °C / 20 mbar / 2 hours.

[1890] A light brown, viscous material with the following general structure was obtained:

[1891]

[1892] It has two anionic counterions, Cl. - and

[1893] Two anionic counterions

[1894]

[1895] in

[1896]

[1897] and among them

[1898]

[1899] Example 35

[1900] Synthesis of di-quaternary ammonium compounds using castor oil-based chloroacetic acid derivatives of lactones.

[1901] In a 1000 ml three-necked flask equipped with a reflux condenser, thermometer, mechanical stirrer, and N2 inlet / outlet, 120.36 g of the solution from Example 31, 167.62 g (0.0797 mol) of the castor oil-based chloroacetic acid intermediate described in Synthesis Example 7a, and 80.6 g of propylene glycol monomethyl ether were mixed at room temperature. The temperature was raised to 115 °C for 31 hours. Volatile substances were then removed under reduced pressure (60 °C / 15 mbar / 1.5 hours).

[1902] A light brown, waxy material with the following general structure was obtained:

[1903]

[1904] It has two anionic counterions, Cl. -

[1905] in

[1906]

[1907] and among them

[1908]

[1909] Synthesis Example 35a

[1910] Synthesis of di-quaternary ammonium compounds using castor oil-based lactone chloroacetate derivatives and having two additional amine salt groups.

[1911] 85.42 g of di-quaternary ammonium from Example 35, 10.4 g (0.0184 mol COOH) of castor oil-stearic acid dimer from Synthesis Example 2a, and 4.7 g of DI water were placed in a 500 ml single-necked flask. The composition was mixed at atmospheric pressure for 2 hours on a rotary evaporator. Volatile substances were then removed at 40 °C / 20 mbar / 2 hours.

[1912] A light brown, waxy material with the following general structure was obtained:

[1913]

[1914] It has two anionic counterions, Cl. - ,and

[1915] Two anionic counterions

[1916]

[1917] in

[1918]

[1919] and among them

[1920]

[1921] Synthesis Example 35b

[1922] Synthesis of di-quaternary ammonium compounds using castor oil-based lactone chloroacetate derivatives and having two additional amine salt groups.

[1923] 89.30 g of di-quaternary ammonium from Example 35, 5.43 g (0.01924 mol COOH) of oleic acid, and 4.7 g of DI water were placed in a 500 ml single-necked flask. The composition was mixed at atmospheric pressure for 1 h on a rotary evaporator. Volatile substances were then removed at 40 °C / 20 mbar / 2 h.

[1924] A light brown, waxy material with the following general structure was obtained:

[1925]

[1926] It has two anionic counterions, Cl. - and

[1927] Two anionic counterions

[1928]

[1929] in

[1930]

[1931] and among them

[1932]

[1933] Examples of scalable processes

[1934] Example 36

[1935] Synthesis of a mixture containing (ricinoleic acid-stearic acid) dimer acids

[1936] In a 500 ml three-necked flask equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, N2 inlet tube, and vacuum outlet, 163.45 g (0.5746 mol) of stearic acid was heated to 70 °C. The flask was gently rinsed with a stream of N2 during the reaction. 81.66 g (0.2736 mol) of ricinoleic acid containing 15% oleic acid and having approximately 70% of the theoretically required free OH groups was added. The mixture was heated to 160 °C for 1 h. An additional 163.34 g (0.5417 mol) of ricinoleic acid was added over 1 h at 160 °C, and this temperature was maintained for 5 h. The temperature was then increased to 200 °C and maintained for 17 h.

[1937] pass 1 1H NMR spectroscopy confirmed the complete conversion of the OH group.

[1938] A gray to light brown wax containing ricinoleic acid-stearic acid dimer as the main component was obtained.

[1939] Castor oil acid-stearic acid dimer (major product approximately 80%)

[1940]

[1941] Ricinoleic acid-ricinoleic acid-stearic acid trimer (approximately 10%)

[1942]

[1943] In addition, approximately 10% of the total is of the following type of acid: (ricinoleic acid) 3-6 - Stearic acid, ricinoleic acid dimer, ricinoleic acid, stearic acid.

[1944] Example 36a

[1945] Synthesis of Chloroacetic Acid Derivatives Based on Castor Oil Laminolidinium

[1946] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, N2 inlet, and gas outlet pipe, 30 g (0.0321 mol) of castor oil was placed and heated to 80 °C. The flask was gently rinsed with a stream of N2 during the reaction. While stirring, 4.25 g (0.0449 mol) of chloroacetic acid was added. The temperature was raised to 120 °C and maintained for 6 hours. Afterward, the temperature was raised to 140 °C and maintained therefore for 5 hours. 1 1H NMR spectroscopy confirmed that each castor oil molecule forms approximately 0.85 chloroacetic acid ester bonds.

[1947] 0.46 g of chloroacetic acid (0.0048 mol) was added and the reaction was continued at 140 °C for another 8 hours.

[1948] pass 1 1H NMR spectroscopy confirmed that each castor oil molecule formed approximately one chloroacetic acid bond.

[1949] Excess chloroacetic acid was removed under reduced pressure (140°C / 25 mbar).

[1950] Add 36.31 g (0.0643 mol) of (ricinoleic acid) 1-stearic acid dimer from Synthesis Example 36. Raise the temperature to 200°C and maintain it for 17 hours.

[1951] pass 1 1H NMR spectroscopy confirmed the complete conversion of the OH groups in castor oil molecules and the formation of additional ester moieties.

[1952] A light brown, waxy material with the following general structure was obtained:

[1953]

[1954] in

[1955]

[1956] and among them

[1957]

[1958] Example 36b

[1959] Synthesis of tetra-quaternary ammonium compounds using castor oil-based chloroacetic acid derivatives of lactones.

[1960] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, and mechanical stirrer, 16.75 g (0.0166 mol tertiary amine) of the tertiary amine solution from Example 31, 23.33 g (0.0111 mol Cl) of the castor oil-based chloroacetic acid intermediate described in Example 36a, and 10.18 g of propylene glycol monomethyl ether were mixed at room temperature. The temperature was raised to 115 °C for 24 hours. Afterward, volatiles were removed under reduced pressure (60 °C / 15 mbar / 1.5 h).

[1961] A light brown, waxy material with the following general structure was obtained:

[1962]

[1963] It has four anionic counterions Cl -

[1964] in

[1965]

[1966] and among them

[1967]

[1968] Synthesis Example 37a

[1969] Synthesis of (2-butanediol-ricinoleic acid) pentameric diol

[1970] In a 100 ml three-necked flask equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, N2 inlet tube, and gas / vacuum outlet, 7.22 g (0.080 mol) of 1,4-butanediol and 47.82 g (0.16 mol) of ricinoleic acid were mixed and heated to 160 °C for 17 hours. A gentle flow of N2 was then passed through the gas volume above the liquid surface.

[1971] The received intermediate with the following approximate structure was 42.16 g (0.065 mol).

[1972]

[1973] 38.66 g (0.13 mol) of ricinoleic acid was mixed in a separate flask and heated to 160 °C for 10 hours. The temperature was then increased to 200 °C for 6 hours. During the reaction, a gentle flow of N2 was passed through the gas volume above the liquid surface.

[1974] A yellow to light brown liquid containing the following average structure as the main component was obtained.

[1975]

[1976] Where R1

[1977]

[1978] Example 37b

[1979] Synthesis of di-quaternary ammonium compounds using chloroacetic acid derivatives of (2-butanediol-ricinoleic acid 2) pentamer diol

[1980] In a 50 ml three-necked flask equipped with a reflux condenser, thermometer, mechanical stirrer, and N2 inlet / outlet, 2.07 g (1.708 mmol) of a 1,4-butanediol-based pentamer from Example 37a and 0.44 g (3.928 mmol) of chloroacetyl chloride were mixed at room temperature. The temperature was raised to 70 °C for 5 hours. Afterward, volatiles were removed under reduced pressure (70 °C / 15 mbar / 1 h).

[1981] Intermediate with the following average structure

[1982]

[1983] Where R1:

[1984]

[1985] 0.59 g (3.416 mmol) of N,N,N',N'-tetramethyl-1,6-hexanediamine and 17.57 g of propylene glycol monomethyl ether were added, and the reaction was continued at 115 °C for 20 h. Volatile substances were removed under reduced pressure (60 °C / 15 mbar / 1 h). 1 The quantitative transformation of the CH2Cl group was determined by H-NMR spectroscopy.

[1986] A yellow liquid-waxy material with the following general structure was obtained:

[1987]

[1988] Where R1

[1989]

[1990] It also possesses two anionic counterions, Cl. - .

[1991] Further application trials

[1992] Damaged hair

[1993]

[1994] The data in the two tables above regarding damaged human hair show that the compounds according to the invention can reduce combing forces on different keratin matrices. The data for compounds 30b and 32a regarding damaged human hair highlight the effectiveness of the inventive materials having a polyfatty acid moiety in both the cationic and anionic forms as a substitute for inorganic anions. The data for compounds 33a, 33b, 34a, and 34b highlight the value of amine salt groups other than quaternary ammonium groups when applied to damaged human hair. The data for compounds 35a and 35b highlight the value of structures with higher melting point moieties in the polyfatty acid chains.

[1995] Hair conditioner application trial:

[1996] Hair conditioning formulation

[1997]

[1998] *: All values ​​for the amount of a component represent "parts by weight based on 100 parts by weight of the whole composition".

[1999] program:

[2000] Phase A and phase B were heated separately at 80°C (phase A) and 60°C (phase B). Phase A was then mixed into phase B.

[2001] After addition, stir the mixture at 60°C for 30 minutes. Add phase C and allow the reaction to reach a temperature of 25°C. Stir phase D for 15 minutes. Store the composition in a suitable container.

[2002] Analysis and summary:

[2003] Each conditioner was evaluated in duplicate, and the average value as shown in the following data was considered the result.

[2004] Combing force measurement procedure:

[2005] The combing force was measured using a Dia-Stron MTT 175 (Dia-Stron Limited) as described above for the combing force measurement.

[2006] 1. Pre-wash Asian hair strands (2.5gm) with 2% NaOH, then wash with 10% SLES.

[2007] 2. Measure the total work done in wet and dry combing.

[2008] Th...

Claims

1. Compounds of general formula (I): R 1 (-F) x (I), in x is 2-20, R 1 Selected from x-valent, optionally substituted linear or branched alkylene or alkenylene groups having 3-200 carbon atoms, and optionally containing one or more groups selected from: -O-, -NH-, -C(O)-, -C(S)-, tertiary amino groups. And it can be substituted by one or more groups selected from OH groups and halogen groups, and F can be the same or different and is represented by general formula (II). The group F binds to R. 1 carbon atoms, and When n is 0, R 3 R 4 R 5 The linear or branched alkyl group, linear or branched alkenyl group, and linear or branched alkynyl group, which may be the same as or different from hydrogen and optionally substituted, having up to 300 carbon atoms, and optionally containing one or more groups selected from: -O-, -NH-, -C(O)-, -C(S)-, tertiary amino group. And it can be substituted by one or more groups selected from OH groups and halogen groups. Where R 3 R 4 R 5 Each is bonded with a carbon atom and a nitrogen atom, and R 3 R 4 R 5 They are not both hydrogen. counterion A of ammonium ions - Selected from monovalent to trivalent inorganic anions and monovalent to decavalent organic anions, and R present in the cation structures of general formulas (I) and (II) 1 R 3 R 4 R 5 At least one of them contains at least one part having formula (III) or (IV): (-XC(O)-R 6 ) m -XC(O)-(III), or (-C(O)-XR 6 ) m -C(O)-X-(IV), in m＝2-20， X is O. R 6 Independently selected from linear or branched alkylene groups, linear or branched alkenyl groups, and linear or branched ynylene groups having 1-36 carbon atoms that are optionally substituted. The condition is that at least one R 6 It has more than 6 carbon atoms.

2. The compound according to claim 1, wherein R 1 Selected from x-valent, optionally substituted linear or branched alkylene or alkenylene groups having 3 to 50 carbon atoms.

3. The compound according to claim 1, wherein R 3 R 4 R 5 It's not hydrogen.

4. The compound according to claim 1, wherein it does not include poly(ethylene oxide) or poly(propylene oxide) units.

5. The compound according to claim 1, wherein R 1 Contains at least one part having general formula (IIIa) or general formula (IVa): (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa), (-C(O)-X-R 6 ) m -C(O)-X-R 7 (IVa) Where X and R 6 and m as defined in claim 1, and R 7 Independently selected from optionally substituted linear or branched alkyl groups, linear or branched alkenyl groups, and linear or branched alkynyl groups, having 1-36 carbon atoms, and optionally containing one or more groups selected from: -O-, -NH-, -C(O)-, -C(S)-, tertiary amino groups. Furthermore, it can be substituted by OH groups or halogen groups, wherein group R 7 It cannot contain a combination of -C(O)- groups and -O- groups that form an internal carboxylic ester group or an internal amide group, or a combination of -C(O)- groups and -NH- or tertiary amino groups.

6. The compound according to claim 1, wherein residue R 1 Contains at least one part of general formula (III) or (IV) (-XC(O)-R 6 ) m -XC(O)-(III), or (-C(O)-XR 6 ) m -C(O)-X-(IV), Where X and R 6 And m as defined above.

7. The compound according to claim 6, wherein residue R 1 Contains at least one part having general formula (IIIa) or general formula (IVa) (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa) (-C(O)-X-R 6 ) m -C(O)-X-R 7 (IVa), Where X and R 6 And m as defined above, R 7 As defined in claim 5.

8. The compound according to claim 1, wherein at least 1% of all groups F contains at least one moiety having general formula (III) or (IV).

9. The compound according to claim 8, wherein 100% of all groups F contain at least one moiety having general formula (III) or (IV).

10. The compound according to claim 5, wherein at least 1% of all groups F contains at least one moiety having the general formula (IIIa) or (IVa).

11. The compound according to claim 10, wherein 100% of all groups F contain at least one portion having the general formula (IIIa) or (IVa).

12. The compound according to claim 1, wherein all groups R 3 R 4 and R 5 At least 1% of it contains at least one part having general formula (III) or (IV).

13. The compound according to claim 12, wherein all groups R 3 R 4 and R 5 At least 10% of it contains at least one part having general formula (III) or (IV).

14. The compound according to claim 5, wherein all groups R 3 R 4 and R 5 At least 1% of it contains at least one part having the general formula (IIIa) or (IVa).

15. The compound according to claim 14, wherein all groups R 3 R 4 and R 5 At least 10% of it contains at least one part having the general formula (IIIa) or (IVa).

16. The compound according to claim 1, wherein in formula (I), x is 2, and the compound has the general formula (V): Where R 1 R 3 R 4 R 5 And n as defined above.

17. The compound according to claim 1, in F has the general formula (VI): And the group F binds to R 1 carbon atoms, in R 3 R 4 R 5 Independently selected from hydrogen, and optionally substituted linear or branched alkyl groups, linear or branched alkenyl groups, and linear or branched alkynyl groups, having up to 300 carbon atoms, and optionally containing one or more groups selected from: -O-, -NH-, -C(O)-, -C(S)-, tertiary amino groups. And it can be replaced by OH. Counterion A -- Selected from monovalent to trivalent inorganic anions and monovalent to decavalent organic anions. The condition is that the group R in the cationic structure of formulas (I) and (II) 1 R 3 R 4 R 5 At least one of them contains at least one part having the general formula (IIIa) or (IVa): (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa) (-C(O)-X-R 6 ) m -C(O)-X-R 7 (IVa) Where X is as defined above. m = 2 - 20, and R 6 Independently selected from optionally substituted linear or branched alkylene groups, linear or branched alkenyl groups, and linear or branched ynynyl groups, having 1-36 carbon atoms, and R 7 Independently selected from optionally substituted linear or branched alkyl groups, linear or branched alkenyl groups, and linear or branched alkynyl groups, having 1-36 carbon atoms, and optionally containing one or more groups selected from: -O-, -NH-, -C(O)-, -C(S)-, tertiary amino groups. Furthermore, it can be substituted by OH groups or halogen groups, wherein group R 7 It cannot contain a combination of -C(O)- groups and -O- groups that form an internal carboxylic ester group or an internal amide group, or a combination of -C(O)- groups and -NH- or tertiary amino groups. The condition is that at least one R 6 It has more than 6 carbon atoms.

18. The compound according to claim 17, wherein R 3 R 4 R 5 It is independently selected from hydrogen and optionally substituted linear or branched alkyl groups, linear or branched alkenyl groups, and linear or branched alkynyl groups, having 1 to 150 carbon atoms.

19. The compound according to claim 17, wherein R 3 R 4 R 5 It is independently selected from hydrogen and optionally substituted linear or branched alkyl groups, linear or branched alkenyl groups, and linear or branched alkynyl groups, having 1 to 20 carbon atoms.

20. The compound according to claim 17, wherein the counterion A - Selected from -Hydrogen anion, -Carboxylate anion.

21. The compound according to claim 17, wherein the counterion A - Selected from -The following types of polymeric fatty acid carboxyl groups R 1 [(-C(O)-XR 6 ) m’ -C(O)-XR 7 ] x’ ,or R 1 [(XC(O)-R 6 ) m’ -XC(O)-R 7 ] x’ , where R 1 Or at least one R 7 Or R 1 and at least one R 7 Both have one or more carboxylate groups, or -The following types of polymeric fatty acid carboxyl groups XR 6 (-C(O)-XR 6 ) m’-1 -C(O)-XR 7 ,or R 6 (-C(O)-X-R 6 ) m’-1 -C(O)-X-R 7 , In the latter two types, R 7 The group has at least one anionic carboxylate group, or -The following types of polymeric fatty acid carboxyl groups R 1 [(-C(O)-X-R6) m’ -C(O)O - ] x’ , And among them X, R 1 R 6 R 7 As defined above, m' = 1 - 20 and x' = 1 - 50.

22. The compound according to claim 17, wherein the counterion A - Selected from - Linear polymeric fatty acid carboxyl groups of the following types - O-C(O)-R 6 -(O-C(O)-R 6 ) m’ -O-C(O)-R 7 , - Dendritic polymer type fatty acid carboxyl group.

23. The compound according to claim 17, wherein the counterion A - Selected from - Branched linear polymeric fatty acid carboxyl groups.

24. The compound according to claim 17, wherein the counterion A - Selected from -Carboxylate anions in poly(acrylic acid) homopolymers and copolymers, wherein the copolymers may have a block or random distribution of comonomer units, or -The carboxylate anion of the maleic acid copolymer, wherein the copolymer may have a block or random distribution of comonomer units, or -Carboxylate anions in poly(itaconic acid) homopolymers and copolymers, wherein the copolymers may have a block or random distribution of comonomer units.

25. The compound according to claim 17, wherein the counterion A- is selected from... -Carboxylate anions in polyacrylic acid copolymers, wherein the copolymers may have a block or random distribution of comonomer units, or - A carboxylate anion in a polyitaconic acid copolymer, wherein the copolymer may have a block or random distribution of comonomer units.

26. The compound according to claim 17, wherein the counterion A- is selected from... -Carboxylate anions in acrylic copolymers containing comonomers that provide OH and amine functional groups that can be functionalized via additional ester or amide bonds, or - A carboxylate anion in a polyacrylic acid copolymer containing a comonomer with a carboxylic acid functional group, wherein the copolymer may have a block or random distribution of comonomer units, or -Carboxylate anions in polyitancica copolymers containing comonomers that provide OH and amine functional groups that can be functionalized via additional ester or amide bonds, or - A carboxylate anion in a polyitancica copolymer containing a comonomer with a carboxylic acid functional group, wherein the copolymer may have a block or random distribution of comonomer units.

27. The compound according to any one of claims 20-26, wherein the counterion A - It can be a pentavalent, tetravalent, trivalent, divalent, or monovalent anion.

28. The compound according to claim 17, wherein the counterion A - Selected from - Chloride, bromide and iodide, sulfate, phosphate, phosphonate, sulfonate, methyl sulfate, -Acetate, propionate, lactate, octanoate, 2-ethylhexanoate, dodecanoate, hexadecanoate, octadecanoate, oleate, ricinoleate, 12-hydroxy-octadecanoate, succinate, maleate, tartrate, polyether carboxylate - Dicarboxylic acid succinic acid and maleic acid with castor oil or Resclere oil as esters.

29. The compound according to claim 17, wherein the group R of the cationic structure of formula (I) and (II) 1 R 3 R 4 R 5 At least one of them contains at least one part having the general formula (IIIa) or (IVa): (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa) (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa) Among them, X and R 6 and R 7 As defined above, and m = 2 - 10.

30. The compound according to claim 29, wherein m is 2, 3, 4, 5 or 6.

31. The compound according to claim 17, wherein the group R of the cationic structure of formula (I) and (II) 1 R 3 R 4 R 5 At least one of them contains at least one part having the general formula (IIIa) or (IVa): (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa) (-C(O)-X-R 6 ) m -C(O)-X-R 7 (IVa) Where X is as defined above. m＝2-20， R 6 Independently selected from optionally substituted linear or branched alkylene groups, linear or branched alkenyl groups, and linear or branched ynylene groups, having 1-24 carbon atoms, R 7 As defined above, The condition is that at least one R 6 It has more than 6 carbon atoms.

32. The compound according to claim 31, wherein R 6 Independently selected from optionally substituted linear or branched alkylene groups, linear or branched alkenyl groups, and linear or branched ynynyl groups, having 8-18 carbon atoms.

33. The compound according to claim 17, wherein the group R of the cationic structure of formula (I) and (II) 1 R 3 R 4 R 5 At least one of them contains at least one part having the general formula (IIIa) or (IVa): (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa) (-C(O)-X-R 6 ) m -C(O)-X-R 7 (IVa) Where X is as defined above. m＝2-20， R 6 As defined above, R 7 Independently selected from optionally substituted linear or branched alkyl groups, linear or branched alkenyl groups, and linear or branched alkynyl groups, having 1-24 carbon atoms, and optionally containing one or more groups selected from: -O-, -NH-, -C(O)-, -C(S)-, tertiary amino groups. Furthermore, it can be substituted by OH groups or halogen groups, wherein group R 7 It cannot contain a combination of -C(O)- groups and -O- groups that form an internal carboxylic ester group or an internal amide group, or a combination of -C(O)- groups and -NH- or tertiary amino groups. The condition is that at least one R 6 It has more than 6 carbon atoms.

34. The compound according to claim 33, wherein R 7 Independently selected from optionally substituted linear or branched alkyl groups, linear or branched alkenyl groups, and linear or branched alkynyl groups, having 8-18 carbon atoms, and optionally containing one or more groups selected from: -O-, -NH-, -C(O)-, -C(S)-, tertiary amino groups. Furthermore, it can be substituted by OH groups or halogen groups, wherein group R 7 It cannot contain a combination of -C(O)- groups and -O- groups that form an internal carboxylic ester group or an internal amide group, or a combination of -C(O)- groups and -NH- or tertiary amino groups.

35. The compound according to claim 1, in R 1 Selected linear or branched alkylene or alkenylene groups with divalent to icosvalent valences, having 3 to 200 carbon atoms, and optionally containing one or more groups selected from: -O-, -NH-, -C(O)-, -C(S)-, tertiary amino groups. And it can be substituted by -OH, and F has the general formula (VI): And the group F binds to R 1 carbon atoms, in R 3 R 4 R 5 Independently selected linear or branched alkyl groups, linear or branched alkenyl groups, and linear or branched alkynyl groups, having up to 200 carbon atoms, and optionally containing one or more groups selected from: -O-, -NH-, -C(O)-, -C(S)-, tertiary amino groups. And it can be replaced by OH. Counterion A -- Selected from monovalent to trivalent inorganic anions and monovalent to decavalent organic anions The condition is that the group R in the cationic structure of formulas (I) and (II) 1 R 3 R 4 R 5 At least one of them contains at least one part having the general formula (VII) or (VIII): -XC(O)-R x -(XC(O)-R x ) m-1 -XC(O)-R 7 (VII), or -XC(O)-R x -(XC(O)-R x ) m -XC(O)-R 7 (VIII) in X is O. m = 2 - 20, and R x +R 7 The total number of carbon atoms in (Σ carbon atoms R) x R 7 The range is 19-150. R x To be optionally subjected to OH, -OC(O)-R 7 -OC(O)-R 6 -(OC(O)-R 6 ) 0-19 -OC(O)-R 7 Substituted straight-chain or branched, saturated or unsaturated hydrocarbon groups having 1-36 carbon atoms and being structures derived from the following corresponding hydroxycarboxylic acids by abstracting a carboxyl group and an OH group: monohydroxycarboxylic acid, dihydroxycarboxylic acid, or polyhydroxycarboxylic acid; R 6 As defined above, R 7 The linear or branched alkyl group, linear or branched alkenyl group, and linear or branched alkynyl group, which may be optionally substituted, have 1 to 36 carbon atoms.

36. The compound according to claim 35, wherein R 1 Selected linear or branched alkylene or alkenylene groups, optionally substituted, of divalent, trivalent, tetravalent, pentavalent, hexavalent, heptavalent, octavalent, nonavalent, or decavalent valence, having 3 to 200 carbon atoms, and optionally containing one or more groups selected from: -O-, -NH-, -C(O)-, -C(S)-, tertiary amino groups. And it can be replaced by -OH.

37. The compound according to claim 35, wherein R 1 It has 3-50 carbon atoms.

38. The compound according to claim 35, wherein R 3 R 4 R 5 Independently selected from optionally substituted linear or branched alkyl groups, linear or branched alkenyl groups, and linear or branched alkynyl groups, having 1 to 20 carbon atoms, and optionally containing one or more groups selected from: -O-, -NH-, -C(O)-, -C(S)-, tertiary amino groups. And it can be replaced by OH.

39. The compound according to claim 35, wherein the counterion A - Selected from -Hydrogen anion, -Carboxylate anion.

40. The compound according to claim 35, wherein the counterion A - Selected from -The following types of polymeric fatty acid carboxyl groups R 1 [(-C(O)-XR 6 ) m’ -C(O)-XR 7 ] x’ ,or R 1 [(XC(O)-R 6 ) m’ -XC(O)-R 7 ] x’ , where R 1 Or at least one R 7 Or R 1 and at least one R 7 Both have one or more carboxylate groups. -or polymeric fatty acid carboxyl groups of the following types XR 6 (-C(O)-XR 6 ) m’-1 -C(O)-XR 7 or R 6 (-C(O)-X-R 6 ) m’-1 -C(O)-X-R 7 , In the latter two types, R 7 The group has at least one anionic carboxylate group. -or polymeric fatty acid carboxyl groups of the following types R 1 [(-C(O)-X-R6) m ’-C(O)O - ] x’ , And among them X, R 1 R 6 R 7 As defined above, m' = 1 - 20 and x' = 1 - 50.

41. The compound according to claim 35, wherein the counterion A- is selected from... - Linear polymeric fatty acid carboxyl groups of the following types - O-C(O)-R 6 -(O-C(O)-R 6 ) m’ -O-C(O)-R 7 , - Dendritic polymer type fatty acid carboxyl group.

42. The compound according to claim 35, wherein the counterion A- is selected from... - Branched linear polymeric fatty acid carboxyl groups.

43. The compound according to claim 35, wherein the counterion A- is selected from... -Carboxylate anions in poly(acrylic acid) homopolymers and copolymers, wherein the copolymers may have a block or random distribution of comonomer units, or -The carboxylate anion of the maleic acid copolymer, wherein the copolymer may have a block or random distribution of comonomer units, or -Carboxylate anions in poly(itaconic acid) homopolymers and copolymers, wherein the copolymers may have a block or random distribution of comonomer units.

44. The compound according to claim 35, wherein the counterion A- is selected from... -Carboxylate anions in polyacrylic acid copolymers, wherein the copolymers may have a block or random distribution of comonomer units, or - A carboxylate anion in a polyitaconic acid copolymer, wherein the copolymer may have a block or random distribution of comonomer units.

45. The compound according to claim 35, wherein the counterion A- is selected from... -Carboxylate anions in acrylic copolymers containing comonomers that provide OH and amine functional groups that can be functionalized via additional ester or amide bonds, or - A carboxylate anion in a polyacrylic acid copolymer containing a comonomer with a carboxylic acid functional group, wherein the copolymer may have a block or random distribution of comonomer units, or -Carboxylate anions in polyitancica copolymers containing comonomers that provide OH and amine functional groups that can be functionalized via additional ester or amide bonds, or - A carboxylate anion in a polyitancica copolymer containing a comonomer with a carboxylic acid functional group, wherein the copolymer may have a block or random distribution of comonomer units.

46. ​​The compound according to claim 35, wherein the counterion A - It can be a pentavalent, tetravalent, trivalent, divalent, or monovalent anion.

47. The compound according to claim 35, wherein the counterion A - Selected from - Chloride, bromide and iodide, sulfate, phosphate, phosphonate, sulfonate, methyl sulfate, -Acetate, propionate, lactate, octanoate, 2-ethylhexanoate, dodecanoate, hexadecanoate, octadecanoate, oleate, ricinoleate, 12-hydroxy-octadecanoate, succinate, maleate, tartrate, polyether carboxylate - Dicarboxylic acid succinic acid and maleic acid with castor oil or Resclere oil as esters.

48. The compound according to claim 35, wherein in at least one portion having general formula (VII) or (VIII): -XC(O)-R x -(XC(O)-R x ) m-1 -XC(O)-R 7 (VII), or -XC(O)-R x -(XC(O)-R x ) m -XC(O)-R 7 (VIII) X, R x and R 7 As defined above, and m is 2-10.

49. The compound according to claim 48, wherein m is 2, 3, 4, 5 or 6.

50. The compound according to claim 35, wherein R x Selected from OH, -OC(O)-R 7 -OC(O)-R 6 -(OC(O)-R 6 ) 0-19 -OC(O)-R 7 Substituted straight-chain or branched, saturated or unsaturated hydrocarbon groups having 8-18 carbon atoms.

51. The compound according to claim 35, wherein R 7 Selected from optionally substituted linear or branched alkyl groups, linear or branched alkenyl groups, and linear or branched alkynyl groups, having 1-36 carbon atoms, and being structures derived from the following corresponding carboxylic acids or hydroxycarboxylic acids by abstracting a carboxyl group: acetic acid, octanoic acid, nonanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, eicosanoic acid, docosanoic acid, 2-ethylhexanoic acid, 2,2-dimethylpropionic acid, 2,2-dimethylheptanoic acid, 2,2-dimethyloctanoic acid, neodecanoic acid, undecano-10-enoic acid, oleic acid, linoleic acid, linolenic acid, and erucic acid.

52. The compound according to claim 1, wherein... R 1 Selected from: a) Linear or branched alkylene or alkenylene groups, optionally substituted with OH or amide, ranging from divalent to octavalent: derived from - Tertiary amines having at least three carbon atoms; - Condensation products of epoxides with alcohols, acids, or primary or secondary amino-functionalized amines; and b) Linear or branched alkylene or alkenylene groups of divalent to octavalent valence, optionally substituted with OH, amino, or amide: which are derived from alkyl halides having more than two carbon atoms; c) Linear or branched alkylene or alkenylene groups of divalent to octavalent valence, optionally substituted with OH, amino, or amide: derived from esters formed by the condensation of a halogenated carboxylic acid having a total of more than two carbon atoms with an alcohol. d) Linear or branched alkylene or alkenylene groups, optionally substituted with OH, ranging from divalent to octavalent: derived from ethers or esters resulting from the reaction of epoxides having a total of more than three carbon atoms with alcohols or acids. e) Linear or branched alkylene or alkenylene groups, optionally substituted with OH, amino, or amide, ranging from divalent to octavalent: formed from an ester of a halocarboxylic acid having a total of more than two carbon atoms with an alcohol or with an acid. f) Linear or branched alkylene or alkenylene groups, optionally substituted with OH, ranging from divalent to octavalent: formed from an ether of an epoxy compound having a total of more than seven carbon atoms and a divalent to hexavalent carboxylic acid. g) Linear or branched alkylene or alkenylene groups, optionally substituted with OH, ranging from divalent to octavalent: It is derived from esters of halogenated carboxylic acids that have a total of more than five carbon atoms.

53. The compound according to claim 52, wherein R 1 Selected from divalent, trivalent, and tetravalent alkylene or alkenylene groups.

54. The compound according to claim 52, wherein under (a), - The tertiary amine is selected from N,N-dimethylethanolamine, N,N-dimethylpropanolamine, N-methylimidazolium, N,N,N',N'-tetramethyl-1,2-diaminoethane, N,N,N',N'-tetramethyl-1,4-diaminobutane, N,N,N',N'-tetramethyl-1,6-diaminohexane, N,N,N',N”,N”-pentamethyl-diethylenetriamine, N,N,N',N”,N”-pentamethyl-dipropylenetriamine, bis-(2-dimethylaminoethyl) ether, bis-(2-dimethylaminopropyl) ether, 2,2'-dimorpholinodiethyl ether, N,N-bis-(3-dimethylaminopropyl)-N-isopropanolamine, N,N,N'-trimethylaminoethyl-ethanolamine, 1,3,5-tris(3-(dimethylamino)propyl)-hexahydro-s-triazine; - The alcohol that forms a condensation product with the epoxide is selected from methanol, ethanol, 2-propanol, 1-butanol, tert-butanol, undecyl-10-enol, oleyl alcohol, stearyl alcohol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,2-hexanediol, 1,6-hexanediol, glycerol, diglycerol, triglycerides and higher linear or branched oligoglycerols, trimethylolpropane, castor oil, pentaerythritol, sorbitol, polyethers based on (ethylene oxide), (propylene oxide) and / or (butane oxide), coethers based on a mixture of (ethylene oxide) and (butane oxide), coethers based on a mixture of (propylene oxide) and (butane oxide), and coethers based on a mixture of (ethylene oxide) and (propylene oxide) and (butane oxide). - Primary and secondary amino-functionalized amines are selected from N,N-dimethylpropylene diamine, N,N,N',N'-tetramethyl... -Diethylenetriamine, N,N,N',N'-Tetramethyl-Dipropylenetriamine, N-Methylmorpholine, N-Methylpiperazine.

55. The compound according to claim 54, wherein under (a), - The alcohol that forms a condensation product with the epoxide is selected from ricinoleic acid triglyceride.

56. The compound according to claim 52, wherein... - Under item b) R 1 Derived from 1,3-dichloropropane, 1,3-dichlorobutane, 1,4-dichlorobutane, and dichloropropane. - Monohydroxypropane isomers, 1,2,3-trichloropropane, 1,2-dichlorohexanediol, 1,2-dichlorohexane, or the corresponding brominated and iodinated derivatives; - Under section c), the halogenated carboxylic acid is selected from chloroacetic acid, 3-chloropropionic acid, 4-chlorobutyric acid, or the corresponding bromocarboxylic acid, and the alcohol is selected from methanol, ethanol, 2-propanol, 1-butanol, tert-butanol, undecyl-10-enol, oleyl alcohol, stearyl alcohol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,2-hexanediol, 1,6-hexanediol, glycerol, diglycerol, triglyceride, etc. Glycerin and higher linear or branched oligoglycerides, trimethylolpropane, castor oil, pentaerythritol, sorbitol, polyethers based on (ethylene oxide), (propylene oxide) and / or (butane), coethers based on a mixture of (ethylene oxide) and (butane), coethers based on a mixture of (propylene oxide) and (butane), and coethers based on a mixture of (ethylene oxide) and (propylene oxide) and (butane); - Under d), alcohols are selected from methanol, ethanol, 2-propanol, 1-butanol, tert-butanol, undecyl-10-enol, oleyl alcohol, stearyl alcohol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,2-hexanediol, 1,6-hexanediol, glycerol, diglycerol, triglycerides and higher linear or branched oligoglycerols, trimethylolpropane, castor oil, pentaerythritol, sorbitol, polyethers based on (ethylene oxide), (propylene oxide) and / or (butane oxide), coethers based on a mixture of (ethylene oxide) and (butane oxide), coethers based on a mixture of (propylene oxide) and (butane oxide), and coethers based on a mixture of (ethylene oxide) and (propylene oxide) and (butane oxide). - Under section e), the halogenated carboxylic acid is selected from chloroacetic acid, 3-chloropropionic acid, 4-chlorobutyric acid, or the corresponding bromocarboxylic acid, and the alcohol is selected from methanol, ethanol, 2-propanol, 1-butanol, tert-butanol, undecyl-10-enol, oleyl alcohol, stearyl alcohol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,2-hexanediol, 1,6-hexanediol, glycerol, diglycerol, triglyceride, etc. Glycerin, and higher linear or branched oligoglycerides, trimethylolpropane, castor oil, pentaerythritol, sorbitol, polyethers based on (ethylene oxide), (propylene oxide) and / or (butane), coethers based on a mixture of (ethylene oxide) and (butane), coethers based on a mixture of (propylene oxide) and (butane), and coethers based on a mixture of (ethylene oxide) and (propylene oxide) and (butane); - Under item f), divalent to hexavalent carboxylic acids are selected from maleic acid, succinic acid, fatty acid, sebaceous acid, itaconic acid, tartaric acid, trimellitic acid, fatty dimer acid, and carboxyl (-C(O)OH) functionalized polyester; -The halogenated carboxylic acid described under item g) is chloroacetic acid, 3-chloropropionic acid, 4-chlorobutyric acid or the corresponding bromocarboxylic acid ester with an OH-functionalized polyester.

57. The compound according to claim 56, wherein... - The alcohol described under section c) is selected from ricinoleic acid triglyceride.

58. The compound according to claim 56, wherein... - The alcohols mentioned under section d) are selected from castor oil triglyceride.

59. The compound according to claim 56, wherein... - The alcohols mentioned under section e) are selected from castor oil triglyceride.

60. The compound according to any one of claims 56-59, wherein -The carboxyl (-C(O)OH) functionalized polyester described under section f) is formed by the condensation of divalent to hexavalent carboxylic acids selected from maleic acid, succinic acid, fatty acid, sebaceous acid, itaconic acid, tartaric acid, trimellitic acid, and fatty dimer acids with divalent to hexavalent alcohols, or epoxides selected from ethylene oxide, propylene oxide, and epoxide butane, and compounds including at least one glycidyl oxy group selected from glycidyl, diglycidyl ether, glycerol diglycidyl ether, glycerol triglycidyl ether, oligoglycerol glycidyl ether, and butanediol diglycidyl ether. - Under item g), the OH-functionalized polyester is formed by the condensation of divalent to hexavalent carboxylic acids selected from maleic acid, succinic acid, fatty acid, sebaceous acid, itaconic acid, tartaric acid, trimellitic acid, and fatty dimer acids with divalent to hexavalent alcohols, or epoxides selected from ethylene oxide, propylene oxide, and epoxide butane, and compounds including at least one glycidyl oxy group selected from glycidyl, diglycidyl ether, glycerol diglycidyl ether, glycerol triglycidyl ether, oligoglycerol glycidyl ether, and butanediol diglycidyl ether.

61. The compound according to claim 60, wherein... -The carboxyl (-C(O)OH) functionalized polyester described under section f) is formed by the condensation of succinic acid, maleic acid and tartaric acid, fatty dimer acid and glycerol diglycidyl ether or the polyester is derived from oligomeric hydroxycarboxylic acids. -The OH-functionalized polyester described under item g) is a condensation product of succinic acid, maleic acid and tartaric acid or a fatty dimer acid with glycerol diglycidyl ether.

62. The compound according to claim 61, wherein, under f), the polyester derived from oligomeric hydroxycarboxylic acids is derived from oligomeric lactic acid, 12-hydroxystearic acid, ricinoleic acid, or hydroxyeicosenoic acid.

63. The compound according to claim 1, in R 1 Selected from - Poly(epoxyalkane) group, or R 1 Selected from - The divalent hydrocarbon group of general formula (X) is derived from oligoglycerol: -[CH2CH(R 8 )CH2O] t1 -[CH2CH(R 8 )CH2)] t2 -(X) in t1＝0-32， t2＝1， R 8 = OH or (-X-C(O)-R 6 ) m -X-C(O)-R 7 、-O-C(O)-R 6 -N + (R 3 ,R 4 ,R 5 ), Where m, X, R 3 R 4 R 5 , and R 6 As defined above, R 7 As defined in claim 5, The condition is that the sum of carbon atoms is 2-100, or R 1 Selected from - Divalent hydrocarbon groups of general formula (XI) and formula (XII) including at least one ester group: -[CH2CH2O] q1 -R 9 -[CH2CH2O] q1 -[CH2CH2] q2 -(XI) Where q1 is the same or different and q1 = 0-49, and q2 = 1, -[CH2CH(R 8 )CH2O] t1 -R 9 -[CH2CH(R 8 )CH2O] t1 -[CH2CH(R 8 )CH2)] t2 -(XII) Where t1, t2 and R 8 As defined above, and R 9 Selected from: -C(O)C(O)O, -C(O)(CH2) 1-8 C(O)O-,, -C(O)CH=CHC(O)O-, -C(O)C(=CH2)-CH2C(O)O-, -C(O)CH(OH)CH(OH)C(O)O-, The condition is that R 9 The sum of the carbon atoms in it is 2-100.

64. The compound according to claim 63, wherein R 1 It contains one or more –O– groups.

65. The compound according to claim 64, wherein the –O– groups are ether groups, or together with the carbonyl groups form an ester group.

66. The compound according to claim 64, wherein R 1 It contains 1-5 –O– groups.

67. The compound according to claim 66, wherein the –O– groups are ether groups, or together with the carbonyl groups form an ester group.

68. The compound according to any one of claims 63-67, wherein the group R 1 It is replaced by one or more hydroxyl groups.

69. The compound according to claim 63, wherein R 1 Poly(epoxyalkane) groups selected from general formula (IX): -[CH2CH2O] q1 -[CH2CH(CH3)O] r1 -[CH2CH(C2H5)O] s1 -{[CH2CH2] q2 - [CH2CH(CH3)] r2 -[CH2CH(C2H5)] s2 }-(IX) in q1＝0-49， r1＝0-32， s1＝0-24， q2 = 0 or 1, r2 = 0 or 1, s2 = 0 or 1, and Σ(q² + r² + s²) = 1, The condition is that the sum of carbon atoms in such poly(epoxyalkane) groups is 2-100.

70. The compound according to claim 63, wherein R 1 It contains one or more ether groups.

71. The compound according to claim 63, wherein R 1 It contains 1-5 ether groups.

72. The compound according to claim 63, wherein R 1 It is replaced by one or more hydroxyl groups.

73. The compound according to claim 1 in When bonded to N + group R 1 R 3 R 4 R 5 When one or more contain at least one part having general formula (III) or (IV) (-XC(O)-R 6 ) m -XC(O)-(III), or (-C(O)-XR 6 ) m -C(O)-X-(IV), Where m = 2 - 20 and X, R 6 As defined above, The at least one part has a structure of general formula (XIII) or (XIV). -R 10 (-XC(O)-R 6 ) m -XC(O)-(XIII), or -R 10 (-C(O)-X-R 6 ) m -C(O)-X-(XIV), in R 10 Selected optional substituted hydrocarbon groups from divalent to hexavalent, having up to 200 carbon atoms and optionally containing one or more groups selected from: -O-, -NH-, -C(O)-, -C(S)-, tertiary amine groups. And it can be substituted by -OH or halogen groups, wherein the group R 10 It cannot contain a combination of -C(O)- groups and -O- groups, or a combination of -C(O)- groups and -NH- or tertiary amino groups, that form an internal carboxylic ester group or an internal amide group, as represented below: - Divalent group, derived from monochlorocarboxylic acids selected from chloroacetic acid, chloropropionic acid, and chlorobutyric acid. - Trivalent group, derived from monochlorocarboxylic acids selected from chloroacetic acid, chloropropionic acid, and chlorobutyric acid, and esters of trivalent alcohols selected from glycerol, trimethylolpropane, and ricinoleic acid triglyceride. -Tetravalent to hexavalent groups, derived from monochlorocarboxylic acids selected from chloroacetic acid, chloropropionic acid, and chlorobutyric acid, and tetravalent alcohols selected from erythritol, pentaerythritol, and diglycerol, pentavalent alcohols selected from xylitol and triglycerol, and partial esters with hexavalent alcohols selected from sorbitol and tritetraglycerol. The condition is that R 10 Connect to N via a single key + Partially attached to at least one group having a structure of general formula (III) or (IV). (-XC(O)-R 6 ) m -XC(O)-(III), or (-C(O)-XR 6 ) m vC(O)-X-(IV), Where X, m, R 6 As defined above.

74. The compound according to claim 73, wherein... When bonded to N + group R 1 R 3 R 4 R 5 When one or more contain at least one part having a general formula (IIIa) or (IVa) (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa) (-C(O)-X-R 6 ) m -C(O)-X-R 7 (IVa) Where m = 2 - 20 and X, R 6 As defined above, and R 7 As defined in claim 5, The at least one part has the structure of general formulas (XIIIa) and (XIVa). -R 10 (-XC(O)-R 6 ) m -XC(O)-R 7 (XIIIa) -R 10 (-C(O)-X-R 6 ) m -C(O)-X-R 7 (XIVa), in R 10 As defined above, The condition is that R 10 Connect to N via a single key + Partially attached to 1, 2, 3, or 4 groups having the general formula (IIIa) or (IVa). (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa) (-C(O)-X-R 6 ) m -C(O)-X-R 7 (IVa) Where X, m, R 6 R 7 As defined above.

75. The compound according to claim 73, wherein R 10 The optionally substituted hydrocarbon group is selected from divalent, trivalent, tetravalent, pentavalent, and hexavalent, having 2-20 carbon atoms and optionally containing one or more groups selected from: -O-, -NH-, -C(O)-, -C(S)-, tertiary amino group. And it can be substituted by -OH or halogen groups, wherein the group R 10 It cannot contain a combination of -C(O)- groups and -O- groups that form an internal carboxylic ester group or an internal amide group, or a combination of -C(O)- groups and -NH- or tertiary amino groups.

76. The compound according to claim 1, in When bonded to N + group R 1 R 3 R 4 R 5 When one or more contain at least one part having general formula (III) or (IV) (-XC(O)-R 6 ) m -XC(O)-(III), or (-C(O)-XR 6 ) m vC(O)-X-(IV), Where m = 2 - 20 and X, R 6 As defined above, The at least one part has a structure of general formula (XIII). -R 10 (-X-C(O)-R 6 ) m -X-C(O)-(XIII), Among them, for the following parts -R 10 (-X-C(O)-R 6 ) m -X-C(O)-(XIII) R 10 Derived from - A mono- or di-(chloroacetic acid) ester of glycerol or castor oil and bonded to a total of one or both moieties (-XC(O)-R) 6 ) m -XC(O)-, Or R 10 Derived from -A tertiary amino alcohol ester, and bonded to a total of one moiety (-XC(O)-R 6 ) m -XC(O)-, Or R 10 Derived from -A tertiary amino alcohol ester, and bonded to a total of two moieties (-XC(O)-R 6 ) m -XC(O)-, Or R 10 Derived from -Tertiary amino alcohol ester, and bonded to a total of more than two moieties (-XC(O)-R 6 ) m -XC(O)-, and R 6 As defined above, m＝2-20。 77. The compound according to claim 76, wherein R 10 Derived from - A mono- or di-(chloroacetic acid) ester of ricinoleic acid triglyceride and bonded to one or both moieties in total (-XC(O)-R 6 ) m -XC(O)-.

78. The compound according to claim 76, wherein for the following portion -R 10 (–X–C(O)–R 6 ) m –X–C(O)–(XIII) R 10 As defined above, R 6 The structures derived from the following corresponding hydroxycarboxylic acids by abstracting a carboxyl group and an OH group are: lactic acid, hydroxyeicosenoic acid, ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, 14-hydroxytetradecanoic acid, R 7 Structures derived from the following corresponding carboxylic acids or hydroxycarboxylic acids by abstracting a carboxyl group: octadecanoic acid, eicosanoic acid, docosanoic acid, 2-ethylhexanoic acid, 2,2-dimethylpropionic acid, neodecanoic acid, oleic acid, and... m = 2, 3, 4, 5, 6 or 7.

79. The compound according to claim 73, in R 6 As defined above, and for the following parts -R 10 (–X–C(O)–R 6 ) m –X–C(O)–(XIII), and -R 10 (–C(O)–X–R 6 ) m –C(O)–X–(XIV), The group R in the ester segment 6 The sequence is random or blocky, and for blocky sequences, the compound contains the general formula (XV) or (XVI): -R 10 -X-C(O)-R 6 (–X–C(O)–R 61 ) m1 (–X–C(O)–R 62 ) m2 -X–C(O)–(XV) -R 10 -C(O)-XR 6 (–C(O)–X–R 61 ) m1 (–C(O)–X–R 62 ) m2 –C(O)–X–(XVI), where R 61 and R 62 Selected from R 6 , m1＝0-20， m2＝0-20， m = (m1 + m2) + 1, m＝2-20。 80. The compound according to claim 79, wherein R 6 The structures derived from the following corresponding hydroxycarboxylic acids by abstracting a carboxyl group and an OH group are: lactic acid, hydroxyeicosenoic acid, ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, and 14-hydroxytetradecanoic acid, and R... 7 It is a structure derived from the following corresponding carboxylic acids or hydroxycarboxylic acids by abstracting a carboxyl group: octadecanoic acid, eicosanoic acid, docosanoic acid, 2-ethylhexanoic acid, 2,2-dimethylpropionic acid, neodecanoic acid, or oleic acid.

81. The compound according to claim 79, wherein the group R within the ester segment 6 The sequence is block-like, and the compound contains a structure of general formula (XV) or (XVI): -R 10 -X-C(O)-R 6 (-X-C(O)-R 61 ) m1 (-X-C(O)-R 62 ) m2 -X-C(O)-(XV) -R 10 -C(O)-XR 6 (-C(O)-XR 61 ) m1 (-C(O)-XR 62 ) m2 -C(O)-X-(XVI), where R 61 and R 62 Selected from R 6 , m1＝0、1、2、3、4、5、6， m2＝0、1、2、3、4、5、6， m = (m1 + m2) + 1, m＝2、3、4、5、6、7， The sequences of the structures of general formulas (XV) and (XVI) are selected from...

82. The compound according to claim 81, wherein the sequences of the structures of general formulas (XV) and (XVI) are selected from...

83. The compound according to claim 79, wherein the group R within the ester segment... 6 The sequence is block-like, and the compound contains a structure of general formula (XVa) or (XVIa): -R 10 -X-C(O)-R 6 (-X-C(O)-R 61 ) m1 (-X-C(O)-R 62 ) m2 -X-C(O)-R 7 (XVa) -R 10 -C(O)-X-R 6 (-C(O)-X-R 61 ) m1 (-C(O)-X-R 62 ) m2 -C(O)-X-R 7 (XVIa) in R 7 As defined in claim 5, R 61 and R 62 Selected from R 6 , m1＝0、1、2、3、4、5、6， m2＝0、1、2、3、4、5、6， m = (m1 + m2) + 1, m = 2, 3, 4, 5, 6, 7, and R 6 +R 7 The total number of carbon atoms in (Σ carbon atoms R) 6 R 7 The range is 19-150. The sequences of the structures of general formulas (XVa) and (XVIa) are selected from...

84. The compound according to claim 83, wherein the sequences of the structures of general formulas (XVa) and (XVIa) are selected from...

85. The compound according to claim 1, Low-melting-point and high-melting-point fatty acids with ≥C5 are positioned in formulas (III) and (IV) containing R in this manner. 6 ester unit (-X-C(O)-R 6 ) m -X-C(O)-(III) (-C(O)-XR 6 ) m -C(O)-X-(IV), Low-melting-point fatty acids with ≥C5 are defined as those with a melting point ≤40℃. Furthermore, high-melting-point fatty acids with ≥C5 are defined as those with a melting point >40℃. The method enables: -Each forms a group R 6 At least one low-melting-point fatty acid of ≥C5 is located in formula (III) or (IV) containing R. 6 At one end of the ester unit, at the same time, one or more groups R are formed at the opposite end of the ester unit of formula (III) or (IV), consisting of at least one high-melting-point fatty acid with a ≥C5 concentration. 6 Or, such that each forms a group R. 6 At least one high-melting-point fatty acid with ≥C5 is located in formula (III) or (IV) containing R. 6 At one end of the ester unit, at the same time, at least one low-melting-point fatty acid of ≥C5 is formed at the opposite end of the ester unit of formula (III) or (IV) by one or more groups R. 6 .

86. The compound according to claim 1, Low-melting-point and high-melting-point fatty acids with ≥C5 are positioned in general formulas (XIII) and (XIV) containing R in this manner. 6 ester unit R 10 (–X–C(O)–R 6 ) m –X–C(O)–(XIII) -R 10 (–C(O)–X–R 6 ) m –C(O)–X–(XIV), Where R 10 As defined in claim 73, Low-melting-point fatty acids with ≥C5 are defined as those with a melting point ≤40℃. Furthermore, high-melting-point fatty acids with ≥C5 are defined as those with a melting point >40℃. The method enables: -Each forms a group R 6 At least one low-melting-point fatty acid with ≥C5 is positioned with the R group 10 Adjacent to each other, at least one high-melting-point fatty acid of ≥C5 is formed at one or more R groups at opposite ends of the ester unit of formula (XIII) or (XIV). 6 , or so that each forms R 6 At least one high-melting-point fatty acid with ≥C5 is formed with the group R 10 One or more adjacent groups R 6 At the same time, at least one low-melting-point fatty acid with ≥C5 is formed in formula (XIII) or (XIV) containing R. 6 and R 7 One or more R groups at opposite ends of the ester unit 6 , where R 7 As defined in claim 5.

87. The compound according to claim 85 or 86, wherein the low-melting-point fatty acid with a melting point ≤40°C and ≥C5 is selected from oleic acid, hydroxyeicosenoic acid, ricinoleic acid, caprylic acid, decanoic acid, tervamolonic acid, and neodecanoic acid, and the high-melting-point fatty acid with a melting point >40°C and ≥C5 is selected from dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, arachidic acid, benzanoic acid, 10-hydroxyoctadecanoic acid, 12-hydroxyoctadecanoic acid, and 14-hydroxytetradecanoic acid.

88. The compound according to claim 85, wherein the low-melting-point and high-melting-point fatty acids with ≥C5 are positioned in such a manner as to contain R in general formulas (IIIa) and (IVa). 6 and R 7 ester unit (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa), and (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa), Where R 7 As defined in claim 5, The method enables: -Each forms a group R 6 At least one low-melting-point fatty acid with ≥C5 is included in R 7 One or more adjacent groups R 6 In this process, at least one high-melting-point fatty acid with ≥C5 is formed in formula (IIIa) or (IVa) containing R. 6 and R 7 One or more R groups at opposite ends of the ester unit 6 , or so that each forms R 6 At least one high-melting-point fatty acid with ≥C5 is formed with R 7 One or more adjacent groups R 6 Formed by at least one low-melting-point fatty acid of formula (IIIa) or (IVa) containing R 6 and R 7 One or more R groups at opposite ends of the ester unit 6 .

89. The compound according to claim 86, wherein the low-melting-point and high-melting-point fatty acids with ≥C5 are positioned in such a manner as to the R-containing compounds of general formulas (XIIIa) and (XIVa). 6 and R 7 ester unit R 10 (-XC(O)-R 6 ) m -XC(O)-R 7 (XIIIa) -R 10 (-C(O)-X-R 6 ) m -C(O)-X-R 7 (XIVa) Where R 7 As defined in claim 5, The method enables: -Each forms a group R 6 At least one low-melting-point fatty acid with ≥C5 is positioned with the R group 10 Adjacent to, and simultaneously forming at least one high-melting-point fatty acid of formula (XIIIa) or (XIVa) with R 7 One or more adjacent groups R 6 , or so that each forms R 6 At least one high-melting-point fatty acid with ≥C5 is formed with the group R 10 One or more adjacent groups R 6 Simultaneously, at least one low-melting-point fatty acid with ≥C5 forms a portion of formula (XIIIa) or (XIVa) with R 7 One or more adjacent groups R 6 .

90. The compound according to claim 1, in When bonded to N + group R 1 R 3 R 4 R 5 When one or more contain at least one part having general formula (III) or (IV) (-XC(O)-R 6 ) m -XC(O)-(III), or (-C(O)-XR 6 ) m -C(O)-X-(IV), Where m = 2 - 20 and X, R 6 As defined above, The at least one part has a structure of general formula (XIII) or (XIV). -R 10 (-XC(O)-R 6 ) m -XC(O)-(XIII), or -R 10 (-C(O)-X-R 6 ) m -C(O)-X-(XIV), Where R 10 Derived from -Contains two or more parts-OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)- castor oil or castor oil triglyceride or glycerol mono- or di-(chloroacetic acid) ester or bonded to a total of one or both moieties -OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7 , esters of tertiary amino alcohols, -Tertiary-primary amine amides The condition is that R 10 Connect to N via a single key + Partially attached to at least one group having a structure of general formula (III) or (IV). (-XC(O)-R 6 ) m -XC(O)-(III), or (-C(O)-XR 6 ) m -C(O)-X-(IV), Where X, m, R 6 As defined above, R 7 As defined in claim 5.

91. The compound according to claim 1, Where R 1 It is formed as follows: - The reaction of halogenated carboxylic acids with OH-functionalized hydrocarbons. - Reactions of halogenated carboxylic acids with epoxy-functionalized hydrocarbons or epoxy esters based on epoxy-functionalized hydrocarbons and difunctional carboxylic acids. - The reaction of glycidyl ethers or glycidyl esters with difunctional carboxylic acids.

92. The compound according to claim 91, wherein the halogenated carboxylic acid is chloroacetic acid.

93. The compound according to claim 1, wherein the counterion A - These are monovalent to trivalent inorganic anions and monovalent to decavalent organic anions, selected from halide anions and carboxylate anions.

94. The compound according to claim 93, wherein the counterion A- is selected from: The following types of polymeric fatty acid carboxyl groups R 1 [(-C(O)-XR 6 ) m’ -C(O)-XR 7 ] x’ ,or R 1 [(XC(O)-R 6 ) m’ -XC(O)-R 7 ] x’ , where R 1 Or at least one R 7 Or R 1 and at least one R 7 Both have one or more carboxylate groups. Or the following types of polymeric fatty acid carboxyl groups XR 6 (-C(O)-XR 6 ) m’-1 -C(O)-XR 7 ,or R 6 (-C(O)-X-R 6 ) m’-1 -C(O)-X-R 7 , In the latter two types, R 7 The group has at least one anionic carboxylate group, or -The following types of polymeric fatty acid carboxyl groups R 1 [(-C(O)-X-R6) m’ -C(O)O - ] x’ , Among them, X and R 1 R 6 As defined above, R 7 As defined in claim 5, x' is 1-50, m' = 1-20.

95. The compound according to claim 93, wherein the counterion A- is selected from: The following types of linear polymeric fatty acid carboxyl groups - OC(O)-R 6 -(OC(O)-R 6 ) m’ -OC(O)-R 7 , where R 7 As defined in claim 5, and m' = 1-20, - Dendritic polymer type fatty acid carboxyl group.

96. The compound according to claim 93, wherein the counterion A- is selected from: - Branched linear polymeric fatty acid carboxyl groups.

97. The compound according to claim 93, wherein the counterion A- is selected from divalent to decavalent poly(acrylic acid) homopolymers and copolymers, poly(itaconic acid) homopolymers and copolymers.

98. The compound according to claim 93, wherein the counterion A - Selected from chloride, bromide, iodide, sulfate, phosphate, phosphonate, sulfonate, methylsulfate, acetate, propionate, lactate, octanoate, 2-ethylhexanoate, dodecanoate, hexadecanoate, octadecanoate, oleate, castor oil, 12-hydroxy-octadecanoate, succinate, maleate, tartrate, polyether carboxylates, branched linear polymeric fatty acid carboxylates derived from dicarboxylic acid succinic acid, and maleic acid with the esters of castor oil or Resclere oil.

99. The compound according to claim 93, wherein the counterion A - Selected from The following types of polymeric fatty acid carboxyl groups - O-C(O)-R 6 (-X-C(O)-R 6 ) m’-1 -X-C(O)-R 7 It is a single-chain molecule without esterified OH substituents. Where R 7 As defined in claim 5, or The following types of polymeric fatty acid carboxyl groups R 1 [(-C(O)-X-R 6 ) m’ -C(O)O - ] x’ It is a carboxylate group containing branched or dendritic units. Where m' = 1 - 20, and x' = 1 - 50.

100. The compound according to claim 1, wherein R 6 Independently selected from optionally substituted linear alkylene or linear alkenyl groups.

101. The compound according to claim 1, wherein R 6 Independently selected from C6-C24 alkylene groups or linear C6-C24 alkenylene groups.

102. The compound according to claim 1, The compound described therein does not contain any amide groups.

103. The compound according to claim 1, wherein the group R present in the cationic structure of general formulas (I) and (II) 1 R 3 R 4 R 5 At least one contains at least one part having the following formula R 1* [(-O-C(O)-R 6 ) m -O-C(O)-]2, Where R 1* It is a divalent C1-C100 alkylene, alkenylene, or ynylene group. m is independently selected from 2-12, and R 6 As defined above.

104. The compound according to claim 103, wherein R 1* It is a C1-C12 alkylene group.

105. The compound according to claim 1, wherein in at least one portion having the following general formula R 1* [(-O-C(O)-R 6 ) m –O–C(O)-]2, R 1* Selected from methylene, ethylene, 1,3-propylene, 1,4-butylene, 1,6-hexylene, 1,2-propylene, and 1,3-butylene. R 6 The structure is derived from the following corresponding hydroxycarboxylic acids by abstracting a carboxyl group and an OH group: C8-C24 monocarboxyl-monohydroxycarboxylic acid. And m is independently selected from 2-6.

106. The compound according to claim 105, wherein R 6 The structure is derived from the following corresponding hydroxycarboxylic acids by abstracting a carboxyl group and an OH group: ricinoleic acid, 12-hydroxystearic acid, hydroxyeicosenoic acid, or 11-hydroxy-undecanoic acid.

107. The compound according to claim 103, wherein the group R present in the cationic structure of general formulas (I) and (II) 1 R 3 R 4 R 5 At least one contains at least one part R having the following general formula 1* [(-OC(O)-R 6 ) m –O–C(O)-]2, It is represented by the following structural formula: -C(O)-O-(mono- or oligomeric C8-C24 hydroxy fatty acids)-C(O)-O-(C2-C10 hydrocarbons)-OC(O)-(mono- or oligomeric C8-C24 hydroxy fatty acids)-OC(O)-, in C2-C10 hydrocarbons are C2-C10 hydrocarbon-like groups, and Mono- or oligomeric C8-C24 hydroxy fatty acids have the following groups: they are derived from hydroxyl-substituted C8-C24 carboxylic acid monomers or oligomers of C8-C24 carboxylic acid monomers with up to 20 hydroxyl-substituted groups formed by esterification, wherein the degree of oligomerization is 2-20.

108. The compound according to claim 107, wherein the degree of oligomerization is 2-6.

109. The compound according to claim 103, wherein the group R present in the cationic structure of general formulas (I) and (II) 1 R 3 R 4 R 5 At least one contains at least one part having the following formula R 1* [(-O-C(O)-R 6 ) m –O–C(O)-R 7 *-]2, Where R 1* R 6 As defined above, m＝2-12， And R 7* It is a C1-C12 alkylene group.

110. The compound according to claim 109, wherein R 7* It is a methylene, ethylene, propylene, or butylene group.

111. The compound according to claim 109, wherein in at least one portion having the following general formula R 1* [(-O-C(O)-R 6 ) m –O–C(O)-R 7 *-]2 R 1* Selected from methylene, ethylene, 1,3-propylene, 1,4-butylene, and 1,6-hexylene. R 6 The structure is derived from the following corresponding hydroxycarboxylic acids by abstracting a carboxyl group and an OH group: C8-C24 monocarboxyl-monohydroxycarboxylic acid. m is independently selected from 2-6. And R 7* Selected from methylene and ethylene.

112. The compound according to claim 109, wherein at least one part has the following general formula R 1* [(-O-C(O)-R 6 ) m –O–C(O)-R 7 *-]2 It can be represented by one of the following structural formulas: i)-CH2-C(O)-O-(mono- or oligomeric C8-C24 hydroxy fatty acids)-C(O)-O-(C2-C10 hydrocarbons)-OC(O)-(mono- or oligomeric C8-C24 hydroxy fatty acids)-OC(O)-CH2- or ii)-CH2CH2-C(O)-O-(mono- or oligomeric C8-C24 hydroxy fatty acids)-C(O)-O-(C2-C10 hydrocarbons)-OC(O)-(mono- or oligomeric C8-C24 hydroxy fatty acids)-OC(O)-CH2CH2-, in C2-C10 hydrocarbons are C2-C10 hydrocarbon-like groups, and Mono- or oligomeric C8-C24 hydroxy fatty acids have the following groups: they are derived from hydroxyl-substituted C8-C24 carboxylic acid monomers or oligomers of C8-C24 carboxylic acid monomers with up to 20 hydroxyl-substituted groups formed by esterification, wherein the degree of oligomerization is 2-20.

113. The compound according to claim 112, wherein the degree of oligomerization in the oligomer formed via esterification is 2-6.

114. The compound of claim 112, wherein the oligomer formed via esterification is derived from mono- or oligomeric ricinoleic acid.

115. The compound according to claim 109, wherein at least one portion has the following general formula R 1* [(-O-C(O)-R 6 ) m -O-C(O)-R 7 *-]2 R at one or both ends 7* The group is bonded to a quaternary N atom.

116. The compound according to claim 115, wherein the two terminal groups R 7* Each is bonded to a quaternary N atom. The compound mentioned therein is a diquaternary ammonium or a four-quaternary ammonium compound.

117. The compound of claim 115, wherein the compound comprises at least two parts having the following general formula R 1* [(-O-C(O)-R 6 ) m -O-C(O)-R 7 *-]2, The portions thereof are connected to each other via di-quaternary ammonium alkylene groups with the following general structure: -N + (CH3)2-ALK-N + (CH3)2-, ALK is a divalent alkylene group having 1-12 carbon atoms.

118. The compound according to claim 117, wherein ALK is a linear alkylene group.

119. The compound according to claim 1, wherein the group R present in the cationic structure of general formulas (I) and (II) 1 R 3 R 4 R 5 At least one contains at least one part having the following general formula: -([-OC(O)-R 6 (-OC(O)-R 6 ) l -OC(O)-LC(O)-O-(R 6 -C(O)-O) l -R 6 -C(O)O])- Where R 6 As defined above, l is independently selected from 0-20, and L is a divalent alkylene or alkenylene group, which may have 1-30 carbon atoms and may optionally contain one or more groups selected from: -O-, -S-, -NH-, -C(O)-, -C(S)-, and tertiary amino groups.

120. The compound according to claim 119, wherein L is selected from methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, vinylene, propenylene, butenylene, pentenylene, hexenylene, heptenylene, octylene, and nonylene.

121. The compound according to claim 119, wherein in at least one portion having the following general formula -([-O-C(O)-R 6 (-O-C(O)-R 6 ) l -O-C(O)-L-C(O)-O-(R 6 -C(O)-O) l -R 6 -C(O)O])- L and l are as defined above. And R 6 Independently, it is a structure derived from the following corresponding hydroxycarboxylic acids by abstracting a carboxyl group and an OH group: C8-C24 monocarboxyl-monohydroxycarboxylic acid.

122. The compound according to claim 119, wherein in at least one portion having the following general formula ([-O-C(O)-R 6 (-O-C(O)-R 6 ) l -O-C(O)-L-C(O)-O-(R 6 -C(O)-O) l -R 6 -C(O)O])- L is selected from methylene, ethylene, and vinylene. R 6 The structures derived from the following corresponding hydroxycarboxylic acids by abstracting a carboxyl group and an OH group are: ricinoleic acid, and l is independently selected from 0, 1, 2 and 3, and the sum of l is in the range of 0-4.

123. The compound according to claim 1, wherein the group R present in the cationic structure of general formulas (I) and (II) 1 R 3 R 4 R 5 At least one contains at least one part having the following general formula: -([-OC(O)-R 6 (-OC(O)-R 6 ) l -OC(O)-LC(O)-O-(R 6 -C(O)-O) l -R 6 -C(O)O])- It is represented by the following structure: -OC(O)-(mono- or oligomeric C8-C24 hydroxy fatty acids)-OC(O)-(C1-C12 hydrocarbons)-C(O)-O-(mono- or oligomeric C8-C24 hydroxy fatty acids)-C(O)-O- in -C1-C12 hydrocarbons are C1-C12 hydrocarbon subgroups, and - Mono- or oligomeric C8-C24 hydroxy fatty acids have the following groups: they are derived from hydroxyl-substituted C8-C24 carboxylic acid monomers or oligomers of up to 20 hydroxyl-substituted C8-C24 carboxylic acid monomers formed by esterification, wherein the degree of oligomerization is 2-20.

124. The compound according to claim 123, wherein the degree of oligomerization is 2-6.

125. The compound according to claim 1, wherein the group R present in the cationic structure of general formulas (I) and (II) 1 R 3 R 4 R 5 At least one contains at least one part having the following general formula: -([-OC(O)-R 6 (-OC(O)-R 6 ) l -OC(O)-LC(O)-O-(R 6 -C(O)-O) l -R 6 -C(O)O])-R 12 -, Where L and l are as defined in claim 119, R 6 As defined above, And R 12 It is a C1-C12 linear or branched alkylene group, which may contain up to 4 -O- groups and up to 4 tertiary amino groups, and is bonded at one end to the -O- group of an ester group and at the other end to a quaternary N atom, and is derived from amino alcohols having the following structure:

126. A process for synthesizing compounds of general formula (I) according to any one of claims 1-125, R 1 (-F) x (I) in The alkyl halide is reacted with a tertiary amine, the tertiary amine containing at least one of the following moieties. (-XC(O)-R 6 ) m -XC(O)-(III), or (-C(O)-XR 6 ) m vC(O)-X-(IV), or The ester of a halogenated carboxylic acid with an alcohol or epoxide is reacted with a tertiary amine, said tertiary amine containing at least one of the following moieties. (-XC(O)-R 6 ) m -XC(O)-(III), or (-C(O)-XR 6 ) m -C(O)-X-(IV), or An epoxy-functionalized ether or ester of an alcohol or carboxylic acid is reacted with a tertiary amine in the presence of an acid, wherein the tertiary amine contains at least one of the following moieties: (-XC(O)-R 6 ) m -XC(O)-(III) or (-C(O)-XR 6 ) m -C(O)-X-(IV), or The reaction involves reacting a hydrocarbon containing a tertiary amino group with an ester of a halogenated carboxylic acid, said ester containing at least one of the following moieties. (–X–C(O)–R 6 ) m –X–C(O)–(III), or (–C(O)–X–R 6 ) m –C(O)–X–(IV), or A hydrocarbon containing a tertiary amino group is reacted with an epoxy-functionalized ether and an ester in the presence of an acid, wherein the epoxy-functionalized ether and ester contain at least one of the following moieties: (–X–C(O)–R 6 ) m –X–C(O)–(III), or (–C(O)–X–R 6 ) m –C(O)–X–(IV), Where X and R 6 m and x as defined in claim 1, and R 7 As defined in claim 5.

127. The process according to claim 126, wherein the ester of the halogenated carboxylic acid is an ester of chloroacetic acid.

128. The process according to claim 126, wherein the epoxy functionalized ether and ester are glycidyl ether and ester.

129. The process of claim 126, wherein the alkyl halide is reacted with a tertiary amine, said tertiary amine containing at least one of the following portions (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa), or (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa), or The ester of a halogenated carboxylic acid with an alcohol or epoxide is reacted with a tertiary amine, said tertiary amine containing at least one of the following moieties. (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa), or (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa), or An epoxy-functionalized ether or ester of an alcohol or carboxylic acid is reacted with a tertiary amine in the presence of an acid, wherein the tertiary amine contains at least one of the following moieties: (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa), or (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa), or The reaction involves reacting a hydrocarbon containing a tertiary amino group with an ester of a halogenated carboxylic acid, said ester containing at least one of the following moieties. (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa), or (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa), or A hydrocarbon containing a tertiary amino group is reacted with an epoxy-functionalized ether and an ester in the presence of an acid, wherein the epoxy-functionalized ether and ester contain at least one of the following moieties: (–X–C(O)–R 6 ) m –X–C(O)–R 7 (IIIa), or (–C(O)–X–R 6 ) m –C(O)–X–R 7 (IVa) Among them, X and R 6 R 7 m and x are as defined in claim 126.

130. The process for synthesizing compounds of general formula (I) according to claim 126, wherein... For compounds of general formula (I) R 1 (–F) x (I), Where R 1 N is attached to quaternized nitrogen atom + And R 1 (-F) x Having at least one part of the general formula (XIII) or (XIV) -R 10 (–X–C(O)–R 6 ) m –X–C(O)–(XIII) -R 10 (–C(O)–X–R 6 ) m –C(O)–X–(XIV), The alkyl halide is reacted with a tertiary amine having at least one moiety of the general formula (XIII) or (XIV). or An ester of a halogenated carboxylic acid is reacted with a tertiary amine having at least one moiety of the general formula (XIII) or (XIV), wherein the ester is formed from an alcohol or an epoxide. or Epoxy-functionalized ethers and esters formed from alcohols or carboxylic acids are reacted with tertiary amines having at least one moiety having the general formula (XIII) or (XIV) in the presence of an acid. or Reacting a hydrocarbon containing a tertiary amino group with an ester of a halocarboxylic acid having at least one moiety of general formula (XIII) or (XIV). or A hydrocarbon containing a tertiary amino group is reacted with an epoxy-functionalized ether and an ester having at least one moiety of general formula (XIII) or (XIV) in the presence of an acid. Where R 10 As defined in claim 73.

131. The process according to claim 130, wherein For compounds of general formula (I) R 1 (-F) x (I), Where R 1 N is attached to quaternized nitrogen atom + And R 1 (-F) x Having at least one part of the general formula (XIIIa) or (XIVa) -R 10 (-XC(O)-R 6 ) m -XC(O)-R 7 (XIIIa) -R 10 (-C(O)-X-R 6 ) m -C(O)-X-R 7 (XIVa) The alkyl halide is reacted with a tertiary amine having at least one moiety having the general formula (XIIIa) or (XIVa). or An ester of a halogenated carboxylic acid is reacted with a tertiary amine having at least one moiety having the general formula (XIIIa) or (XIVa), said ester being formed from an alcohol or an epoxide. or Epoxy-functionalized ethers and esters formed from alcohols or carboxylic acids are reacted with tertiary amines having at least one moiety having the general formula (XIIIa) or (XIVa) in the presence of an acid. or Reacting a hydrocarbon containing a tertiary amino group with an ester of a halocarboxylic acid having at least one moiety of the general formula (XIIIa) or (XIVa). or A hydrocarbon containing a tertiary amino group is reacted with an epoxy-functionalized ether and an ester having at least one moiety of general formula (XIIIa) or (XIVa) in the presence of an acid. Where R 10 As defined above.

132. Use of the compound of claim 1 in cosmetic formulations for hair care.

133. The use according to claim 132, wherein the cosmetic formulation for hair care is selected from conditioning agents and shampoos.

134. Use of the compound of claim 1 in a cosmetic composition for treating human hair.

135. The use according to claim 134, wherein the use in the cosmetic composition is for strengthening hair, for maintaining hair color, for enhancing hair shine, for enhancing hair color, for protecting hair color, for styling hair, for conditioning hair, for smoothing or softening hair, and for improving hair manageability.

136. The use according to claim 135, wherein the compound of claim 1 is used in a cosmetic composition for hair styling, specifically for curling and straightening hair.

137. The use according to claim 135, wherein the use of the compound of claim 1 in a cosmetic composition for improving hair manageability is to improve hair combability, anti-frizz and antistatic properties.

138. A composition for treating hair, comprising the compound of claim 1, selected from hair shampoo compositions, hair conditioning compositions, hair strengthening compositions, hair coloring or dyeing compositions, hair combability improvement compositions, anti-frizz compositions, rinsing and leave-in hair compositions.

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