Fibrous amino acid-based substrates, particularly fatty acid polymer compounds for hair treatment

Abstract

The present invention relates to a mono-, di-, or polyquaternary ammonium compound of formula (I). R1(-F)x(I) Here, x is 1 to 50, and F is the same or different and is represented by the chemical formula (II), Here, at least one of the optionally substituted and optionally functionalized hydrocarbon radicals R1, R2, R3, R4, or R5 contains at least one estolide moiety comprising two or more ester or amide moietyes. Additionally, the present invention relates to a method for synthesizing such compounds, the use of the compounds in cosmetic formulations for skin and hair care, cosmetic compositions for textile treatment, and compositions for hair treatment comprising one or more compounds.

Description

Technology Field

[0001] The present invention relates to a fatty acid polymer compound, a method for preparing the same, a composition containing said compound, and in particular, the use of said compound in a cosmetic composition for skin and hair care, which is a hair care composition, and the use of said compound for hair treatment. Background Technology

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

[0003] The basic component of hair is cross-linked alpha-helical protein keratin. Keratin is an intermediate filament protein found particularly in epithelial cells, such as human skin and hair, wool, bird feathers, and nails. Alpha-helical type I and II keratin intermediate filament proteins (KIF), with a molecular weight of about 45-60 kDa, are embedded within an amorphous matrix of keratin-assisted proteins (KAP), with a molecular weight of 20 to 30 kDa (MA Rogers, L. Langbein, S. Praetzel-Wunder, H. Winter, J. Schweizer, J. Int Rev Cytol. 2006; 251:209-6); and both intramolecular and intermolecular disulfide bonds provided by cystine contribute to a cytoskeletal protein network that maintains cell scaffolding. In addition to the disulfide crosslinking mentioned above, ionic bonds or salt bridges connecting various amino acids found in hair proteins contribute to the external shape of the 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 color retention, as well as conditioning, gloss, and UV protection. Typically, these silicone and hydrocarbon-based derivatives are physically deposited on the fiber surface (cuticle) to provide the hair's appearance, namely softness, silkiness, friction, alignment, and combability.

[0005] Advanced silicone derivatives are generally considered high-performance materials in relation to properties such as a soft, silky hair feel, reduced friction, easy combing, and hair color protection. Quaternized silicones are described in prior art literature, namely US 4891166, EP 282720, 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, the mono-quaternary ammonium compound is a mono-long alkyl-trishort alkyl quaternary ammonium salt or a di-long alkyl-dishort alkyl quaternary ammonium salt, wherein one or two alkyl substituents are selected from an aliphatic group having about 8 to about 30 carbon atoms or an aromatic, alkoxy, polyoxyalkylene, alkylamido, hydroxyalkyl, aryl, or alkylaryl group having up to about 30 carbon atoms; and the other alkyl group is independently selected from an aliphatic group having about 1 to about 8 carbon atoms or an aromatic, alkoxy, polyoxyalkylene, alkylamido, hydroxyalkyl, aryl, or alkylaryl group having up to about 8 carbon atoms; The counterion is a salt-forming anion selected from halogens (e.g., chloride, bromide), acetate, citrate, lactate, glycolate, phosphate, nitrate, sulfonate, sulfate, alkyl sulfate, glutamate, and alkyl sulfonate radicals. Alternatively, these mono-quaternary ammonium compounds are saturated or unsaturated fatty acid-based mono-fatty esters and di-fatty ester quarts, as well as fatty amido quarts having alkyl chain(s) of 10 to 24 carbon atoms. Details regarding these substances containing quaternary ammonium groups are disclosed, for example, in US 2009 / 0000638, WO 2012 / 027369, US 2013 / 259820 and US 5880086, US 6465419, US 6462014, US 6323167, US 6037315, US 5854201, US 5750490, US 5463094, and US 2003 / 013627.

[0007] Di-quaternized hydrocarbons are also known. Typically, these geomini quarts are based on C8 to C20 alkyl or fatty chains (D.Shukla et al., Cationic Gemini Surfactants: A Review, Journal of Oleo Science 2006, Vol. 55, Nr. 8, 381-390; MJ Rosen et al. Langmuir (2001), 17, 6148-6154).

[0008] Di-quaternary hydrocarbons based on cross-copolyesters of castor oil and other dicarboxylic acids are described in US 2003 / 0007950 and US 6972123.

[0009] A castor oil precursor was used for the synthesis of a substance containing three quart groups (EP 0283994, A. Baydar et. al., International Journal of Cosmetic Science (1991), 13(4), 169-90).

[0010] A fatty acid dimer was used in the synthesis of a polyquaternary fatty acid dimer copolymer (US 6982078).

[0011] WO 2004 / 093834 describes hydrocarbon monoquaternary compounds for personal care applications. These compounds are -CH2CH2O-EO x -PO y - It essentially includes a linker having a structure. Polymerized fatty acids have been proposed as hydrophobic tails.

[0012] There has been a demand for fibrous amino acid-based substrates, particularly compounds efficient for hair treatment, that are primarily based on sustainable raw materials, can be synthesized in a simple, cost-effective, and flexible manner, are easy to formulate and use, produce a long-term stable formulation even in the presence of other performance ingredients, and are useful for hair conditioning, improving hair dry and wet combing, and hair softness and pleasant alignment. In particular, benefits regarding improved wet and dry combing comparable to silicone-based conditioning agents must be achieved.

[0013] The inventors have discovered that novel fatty acid polymeric mono-, di-, and poly-quaternary compounds, namely mono-, di-, and poly-quaternary compounds comprising an estolide structure, and aqueous compositions comprising such compounds are suitable for satisfying the aforementioned requirements. Accordingly, the present invention provides novel fatty acid polymeric mono-, di-, and poly-quaternary estolide compounds, aqueous compositions comprising the same, cosmetic compositions comprising the same, particularly hair care compositions, and uses thereof for hair treatment, wherein the fatty acid polymeric mono-, di-, and poly-quaternary estolide compounds can be manufactured in a simple, cost-effective, and flexible manner based mainly on sustainable raw materials, are easy to formulate and use, and are useful for hair conditioning, improving dry and wet combing of hair, and hair softness and pleasant alignment. The problem to be solved

[0014] The present invention relates to a fatty acid polymer compound, a method for preparing the same, a composition containing said compound, and in particular, the use of said compound in a cosmetic composition for skin and hair care, which is a hair care composition, and the use of said compound for hair treatment. means of solving the problem

[0015] According to the present invention, a compound of the following chemical formula is provided.

[0016] R1 (-F) x (I)

[0017] Here,

[0018] x is 1 to 50, preferably 2 to 50, and

[0019] R 1 It is selected from an arbitrarily substituted hydrocarbon radical of x, which has up to 1000 carbon atoms, preferably 2 to 300 carbon atoms, more preferably 3 to 200 carbon atoms, even more preferably 3 to 150 carbon atoms, specifically 3 to 50 carbon atoms, more specifically 3 to 20 carbon atoms, -O, NH, -C(O)-, -C(S)-, tertiary amino group ( It may optionally contain one or more groups selected from ), and may be substituted with one or more groups selected from OH groups and halogen groups, and

[0020] F may be the same or different and is represented by the chemical formula (II),

[0021]

[0022] Here, the F units are R 1 Bonded to the carbon atoms of,

[0023] n is independently 0 to 100, and

[0024] R 2 may be identical or different and is selected from divalent, optionally substituted hydrocarbon radicals having up to 1000 carbon atoms, -O-, -NH-, -C(O)-, -C(S)-, tertiary amino group ( Optionally containing one or more groups selected from ), and may be substituted with one or more groups selected from OH groups and halogen groups, and

[0025] R 3 , R 4 , R 5It may be identical or different and may be selected from hydrogen and optionally substituted straight-chain, cyclic or branched, saturated, unsaturated, or aromatic hydrocarbon radicals having up to 1000 carbon atoms, and -O-, -NH-, -C(O)-, -C(S)-, tertiary amino group ( ), quaternary ammonium group ( Optionally containing one or more groups selected from ), and may be substituted with one or more groups selected from OH groups and halogen groups, and

[0026] Here, R 3 , R 4 , R 5 Each bonds to a nitrogen atom as a carbon atom, and

[0027] Preferably R 3 , R 4 , R 5 is not hydrogen,

[0028] Counterion A of the ammonium ion - is selected from monovalent to trivalent inorganic anions and monovalent to 30,000, preferably monovalent to 1,000, organic anions, and

[0029] R present in the cation structures of chemical formulas (I) and (II) 1 , R 2 , R 3 , R 4 , R 5 At least one of them contains at least one moiety of chemical formula (III) or (IV):

[0030] (-XC(O)-R 6 ) m -XC(O)- (III) or

[0031] (-C(O)-XR 6 ) m -C(O)-X- (IV),

[0032] Here

[0033] m = 1 to 20, and

[0034] X is O or NR 11 is,

[0035] R 11 is independently selected from the group consisting of hydrogen, or optionally substituted straight-chain, cyclic or branched, saturated, unsaturated, or aromatic hydrocarbon radicals having up to 100 carbon atoms, and -O-, -NH-, -C(O)-, -C(S)-, tertiary amino group ( It optionally contains one or more groups selected from ), and can be substituted with one or more hydroxyl and halogenated groups, and

[0036] R 6 The radical is independently selected from optionally substituted straight-chain, cyclic, or branched, saturated or unsaturated hydrocarbon radicals having 1 to 36 carbon atoms, and

[0037] However, at least one R 6 It has more than 6 carbon atoms, and

[0038] For x = 1

[0039] R 1 , R 3 , R 4 , R 5 It does not bond to the nitrogen atom of the group below through -OCH2CH2-.

[0040] Effects of the invention

[0041] The inventors have discovered that novel fatty acid polymeric mono-, di-, and poly-quaternary compounds, namely mono-, di-, and poly-quaternary compounds comprising an estolide structure, and aqueous compositions comprising such compounds are suitable for satisfying the aforementioned requirements. Accordingly, the present invention provides novel fatty acid polymeric mono-, di-, and poly-quaternary estolide compounds, aqueous compositions comprising the same, cosmetic compositions comprising the same, particularly hair care compositions, and uses thereof for hair treatment, wherein the fatty acid polymeric mono-, di-, and poly-quaternary estolide compounds can be manufactured in a simple, cost-effective, and flexible manner based mainly on sustainable raw materials, are easy to formulate and use, and are useful for hair conditioning, improving dry and wet combing of hair, and hair softness and pleasant alignment. Specific details for implementing the invention

[0042] According to the present invention, estolides are natural and synthetic compounds derived particularly from fats and oils, more specifically from fatty acid compounds that can be obtained by the hydrolysis of oils and fats.

[0043] The above estolide structure is identified by the secondary ester bond of one fatty acyl molecule to the alkyl backbone of another fatty acid fragment. Although the terms “fatty acid” and “fatty acyl molecule” appear to imply that individual residues must be derived from components of fat, this is not actually the case. In this specification, the term “fatty acid” refers to a carboxylic acid having a chain-like organyl group, in particular an unbranched aliphatic monocarboxylic acid. Fatty acids differ from one another by the number of their carbon atoms (chain length), and, when referring to unsaturated fatty acids, by the number and position of double bonds. Fatty acids may be classified into short-chain fatty acids having up to 7 carbon atoms, medium-chain fatty acids having 8 to 12 carbon atoms, long-chain fatty acids having 13 to 21 carbon atoms, and extra-long-chain fatty acids having more than 22 carbon atoms.

[0044] According to the present invention, the "-O-" group generally represents an ether group, which also includes the presence of an epoxide moiety that is a ternary ring ether group. Accordingly, the group defined above as optionally containing the "-O-" group may contain an epoxy group. This is particularly applicable to a residue R that may include the terminal epoxy group defined above. 3 , R 4 and R 5 It applies to.

[0045] According to the present invention, residue R 1 is x, where x is 1 to 50, preferably 2 to 50, and this is residue R 1 This indicates that it contains x residue F as defined by this chemical formula (II). Thus, the term "x" refers to a residue R that may be a hydroxyl group and a halogen group. 1 It does not indicate or limit the number of any additional substituents other than F.

[0046] According to the present invention, the term “optionally substituted hydrocarbon radical,” which may optionally contain one or more specific groups and may be substituted with one or more specific groups, is an organyl radical that may be connected to one or more additional groups through at least one of its carbon atoms, wherein the hydrocarbyl structure of the radical may be interrupted by a specific group defined as containing, and one or more hydrogen atoms of the hydrocarbyl group may be substituted with a substituent as indicated.

[0047] For example, R 1 In the case of, one or more hydrogen atoms may be substituted by hydroxyl groups or halogenated substituents, namely fluoro, chloro, bromo, or iodo substituents.

[0048] Additionally, an arbitrarily substituted hydrocarbon radical R 1 Specifically, -O-, -NH-, -C(O)-, -C(S)- and tertiary amino groups Since it may contain one or more groups selected from, R 1 The hydrocarbyl structure of the group may be interrupted by these groups or combinations thereof. Thus, the residue may contain ester groups, carboxyl groups, amide groups, ether groups, amino groups, carbonyl groups, thion groups, thiocarboxylate groups, thioester groups, carbamate groups, urethane groups, epoxide groups, and all other groups specified for these radicals, and combinations thereof. The same principle applies to selectively substituted hydrocarbon radicals R 2 , R 3 , R 4 , R 5 , R 6 and R 11 It applies to.

[0049] R, where x is the value corresponding to the residue F. 1The hydrocarbyl structure is preferably selected from the group consisting of linear, branched or cyclic alkyl or alkylene groups, linear, branched or cyclic alkenyl or alkenylene groups, linear, branched or cyclic alkynylene groups, linear, branched or cyclic alkalyl or alkalylene groups, linear, branched or cyclic aralkyl or aralkylene groups and linear, branched or cyclic aryl or arylene groups, such as phenyl or phenylene, benzyl or benzylene or tolyl or tolylene groups, in particular from groups having 1 to 30 carbon atoms.

[0050] More preferably, x is R 1 The radical is selected from alkyl or alkylene groups, which may be selected from linear, branched, and cyclic alkyl or alkylene groups or groups combined with linear and cyclic alkyl or alkylene structures, or groups combined with branched and cyclic structures, in particular 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 groups, linear C1-C22 alkyl groups such as iso-propyl and iso-propylene, iso-butyl and iso-butylene, tert-butyl and tert-butylene, iso-pentyl and iso-butylene, tert-pentyl and tert-pentylene, neo-pentyl and It may be selected from branched C1-C22 alkyl and alkylene groups such as neo-pentylene, 2-ethylhexyl and 2-ethylhexylene groups, cyclopropyl or cyclopropylene, cyclobutyl and cyclobutylene, cyclopentyl and cyclopentylene, cyclohexyl and cyclohexylene, and cyclic C3-C22 alkyl groups such as cycloheptyl or cycloheptylene groups.

[0051] If x > 1, R 1 There are no restrictions on the C-atom of the hydrocarbyl radical, which are the F groups bonded to R 1and with respect to the presence of a functional group arbitrarily contained in any substituent, R 1 is derived from glycidyl compounds, glycerol and glycerol derivatives, in particular glycidol, glycerol, glycerol diglycidyl ether, diglycidyl ether, and polyglycerol compounds, or R 1 This is a linear alkylene group, specifically an alkylene group that does not have additional substituents other than the F group.

[0052] As mentioned above, R 1 It is particularly preferable that this is derived from glycerol diglycidyl ether, wherein the epoxide ring of the glycerol diglycidyl ether is opened by the N atom and R in the compound according to the present invention 1 By forming a quaternary N atom adjacent to the group, R 2 It means that is formed. In the same way, R 1 It is preferable that this be derived from diglycidyl ether, diglycerol diglycidyl ether, triglycerol diglycidyl ether, polyglycerol terminated with a glycidyl unit, and poly(alkylene oxide) compounds terminated with a glycidyl unit, in particular poly(ethylene oxide) terminated with a glycidyl unit, poly(propylene oxide) terminated with a glycidyl unit, and poly(butylene oxide) terminated with a glycidyl unit.

[0053] Also, R 1 It is preferable that this be formed from a compound obtained by the esterification of this polyol and an ω-halocarboxylic acid, in particular the polyol is a diol compound such as an α,ω-diol or an α,ω-dihydroxypolyether, more specifically dihydroxy-terminated poly(ethylene oxide), dihydroxy-terminated poly(propylene oxide), or dihydroxy-terminated poly(butylene oxide), and in particular the ω-halocarboxylic acid is ω-chloroacetic acid or ω-chloropropanoic acid. The latter compound is R 1 R by substitution of a chloro substituent by the N-atom of the F group adjacent to the group 1forms.

[0054] According to this, R 1 It is preferable that this is a C3-C50 alkylene group containing one or more internal ether or ester groups, and R 1 It is particularly preferable for this to be an alkylene group having a hydroxyl substituent.

[0055] R 1 This is a linear C1-C8 alkylene group without additional substituents or functional groups, or R 2 It is most preferable that the linear C3 to C50 alkylene group is derived from diglycidyl ether, glycerol diglycidyl ether, diglycerol diglycidyl ether, diethylene glycol diglycidyl ether, or ethylene glycol diglycidyl ether having 3 to 10 (ethylene oxide) repeating units.

[0056] According to the present invention, the term “optionally substituted hydrocarbon residue” does not impose any additional restrictions on radicals, and thus they are limited by groups that are optionally contained or present as substituents depending on the number of carbon atoms of the residue, and by the way they are bonded to other structural moieties of the compound according to the present invention, as defined by formulas (I), (II), (III), (IV) or other additional formulas used to define embodiments according to the present invention.

[0057] For example, R 2 In the case of, the term "2-ga" is R 2 It refers to being bonded to two quaternary N atoms according to chemical formula (II), but R 2 It does not restrict the existence of additional substituents as defined for.

[0058] Therefore, residual R 2 , R 3 , R 4 , R 5 , R 6 and R11 can be an arbitrarily substituted straight-chain, cyclic or branched, saturated, unsaturated, or aromatic hydrocarbon radical, where R 2 and R 6 is a divalent radical, and R 3 , R 4 , R 5 and R 11 It is a monovalent radical.

[0059] According to chemical formula (II), R 2 is bonded to two different quaternary N atoms, and R 6 It is bonded to the carboxyl group of a carboxylate or amide moiety on one side, and to the O atom of the carboxylate group or the NR of the amide group on the other side. 11 It is combined with X groups that can be groups, and applies, for example, to the definition of formula (III) or (IV) as well as to additional formulas according to additional embodiments of the present invention.

[0060] Radical R 3 , R 4 , R 5 and R 11 It may be the same or different and is a monovalent radical selected from hydrogen and optionally substituted linear, cyclic or branched, saturated, unsaturated, or aromatic hydrocarbon radicals having up to 1000 carbon atoms, and thus, for example, may be a linear, cyclic or branched alkyl group, a linear, cyclic or branched alkenyl group, a linear, cyclic or branched alkynyl group, a linear, cyclic or branched alkaryl group, a linear, cyclic or branched aralkyl group and an aryl group, for example, may be a phenyl, benzyl, or tolyl group, and in particular may be a group having 1 to 30 carbon atoms, and the aforementioned group may optionally be substituted with OH or a halogen group, and optionally -O-, NH-, -C(O)-, -C(S)-, tertiary amino group ( ) and quaternary ammonium group ( It may contain one or more groups selected from ).

[0061] Preferably, radical R 3 , R 4 , R 5 and R 11 The radical R is selected from alkyl groups, which may be selected from the group consisting of linear, branched, and cyclic alkyl groups or groups combined with linear and cyclic alkyl motifs, and structures combined with branched and cyclic structures, and in particular may be selected from linear C1-C22 alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, 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, and more preferably the radical R 3 , R 4 , R 5 and R 11 It is selected from methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, or cyclohexyl groups, most preferably methyl.

[0062] Radical R according to the present invention 2 It may be identical or different and is selected from divalent, optionally substituted hydrocarbon radicals having up to 1000 carbon atoms, which are -O-, -NH-, -C(O)-, -C(S)-, tertiary amino groups ( It optionally contains one or more groups selected from ), and may be substituted with one or more groups selected from OH groups and halogen groups, preferably selected from the group consisting of linear, branched or cyclic alkylene groups, linear, branched or cyclic alkenylene groups, linear, branched or cyclic alkynylene groups, linear, branched or cyclic alkalylene groups, linear, branched or cyclic aralkylene groups and linear, branched or cyclic arylene groups, e.g., phenylene, benzylene, or tolylene groups, and is particularly selected from these groups having 1 to 100 carbon atoms, each optionally containing one or more functional groups as described above.

[0063] More preferably, R 2 The radical is selected from alkylene groups, which may be selected from the group consisting of linear, branched, and cyclic alkylene groups or groups combined with linear and cyclic alkylene structures, or groups combined with branched and cyclic structures, and in particular is selected 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 iso-propylene, iso-butylene, tert-butylene, tert-pentylene, neo-pentylene, and 2-ethylhexylene groups, and cyclic C3-C22 alkyl groups such as cyclopropylene, cyclobutylene, cyclopentylene, cyclohexylene and cycloheptylene groups.

[0064] quaternary N valence R 2 There are no restrictions on the C-atom of the hydrocarbyl radical that is bonded to it.

[0065] R 2 With respect to the presence of optionally contained functional groups and optional substituents, R 2 It is preferably derived from glycidyl compounds, glycerol, and glycerol derivatives, and in particular derived from glycidol, glycerol diglycidyl ether, diglycidyl ether, and polyglycerol compounds, or R2 In the case where the alkylene group is linear, an alkylene group that does not have additional substituents other than a quaternary N atom is particularly preferred.

[0066] As mentioned above, R 2 It is particularly preferable that is derived from glycerol diglycidyl ether, which opens the epoxide ring of glycerol diglycidyl ether by the N atom and R in the compound according to the present invention 2 R by forming a quaternary N atom adjacent to the group 2 This means that is formed. In the same way, R 2 It is preferable that it be derived from diglycidyl ether, diglycerol diglycidyl ether, triglycerol diglycidyl ether, polyglycerols terminated with a glycidyl unit, and poly(alkylene oxide) compounds terminated with a glycidyl unit, in particular poly(ethylene oxide) terminated with a glycidyl unit, poly(propylene oxide) terminated with a glycidyl unit, and poly(butylene oxide) terminated with a glycidyl unit.

[0067] Also, R 2 It is preferable that it be formed from a compound obtained by the esterification of a diol compound and an ω-halocarboxylic acid, in particular the diol is an α,ω-diol or α,ω-dihydroxypolyether, particularly specifically dihydroxy-terminated poly(ethylene oxide), dihydroxy-terminated poly(propylene oxide) or dihydroxy-terminated poly(butylene oxide), and in particular the ω-halocarboxylic acid is ω-chloroacetic acid or ω-chloropropanoic acid. The latter compound is R 2 R by substitution of a chloro substituent by an N-atom adjacent to the group 2 forms.

[0068] According to this, R 2 It is preferable that is a C3-C50 alkylene group containing one or more internal ether or ester groups, and R 2It is particularly preferable that the alkylene group is one having a hydroxyl substituent.

[0069] R 2 g is a linear C1-C8 alkylene group without additional substituents or functional groups, or R 2 It is most preferable that the linear C3 to C50 alkylene group is derived from diglycidyl ether, glycerol diglycidyl ether, diglycerol diglycidyl ether, diethylene glycol diglycidyl ether, or ethylene glycol diglycidyl ether having 3 to 10 (ethylene oxide) repeating units.

[0070] Radical R 6 It may be identical or different and may represent a hydrocarbyl group selected from optionally substituted linear, cyclic or branched, saturated or unsaturated hydrocarbon radicals having 1 to 36 carbon atoms, and thus from the group consisting of linear, branched or cyclic alkylene groups, linear, branched or cyclic alkenylene groups, linear, branched or cyclic alkynylene groups, linear, branched or cyclic alkylylene groups, linear, branched or cyclic arylkylene groups and linear, branched or cyclic arylene groups, e.g., phenylene, benzylene or tolylene groups, and in particular from groups having 1 to 100 carbon atoms, each optionally containing one or more functional groups as indicated above.

[0071] More preferably, R 6The radical is selected from linear alkylene groups and linear alkenylene groups, in particular linear C6-C24 alkylene groups such as hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, doicosylene, tricosylene, and tetraicosylene, or linear C6-C24 alkenylene groups, e.g., hexenylene, heptenylene, octenylene, nonenylene, decenylene, undecenylene, dodecylene, tridecylene, hexadecylene, octadecenylene, nonadecenylene, eicosenylene, henicosylene, doicosenylene, tricosenylene and linear C6-C24 alkenylene groups such as tetraicosenylene, wherein it is most preferable that the group be bonded to an adjacent C(O) group by a terminal C-atom.

[0072] The C-valence R of the hydrocarbyl radical of the adjacent C(O) and X groups 6 There are no restrictions on what is combined with it.

[0073] However, R 6 is preferably derived from a hydroxycarboxylic acid having one or more hydroxyl groups, more preferably from a monohydroxycarboxylic acid, and most preferably from a C7-C25 fatty acid having one hydroxyl group as a substituent. Therefore, R 6 is preferably an alkylene or alkenylene chain of such a carboxylic acid. For example, R 6 In the case of this derived from ricinoleic acid, R 6 represents a 1,11-heptadex-8-enyl radical, where "1,11" indicates the position where the radical is bound to adjacent groups X and C(O).

[0074]

[0075] R of at least one moiety present within the cation structure of formula (I) as defined by formula (III) or formula (IV).6 - The number of m of the containing repeating unit (-XC(O)-R6) or (-C(O)-X-R6) is 1 to 20, preferably 1 to 15, 1 to 12, 1 to 10, 1 to 8, or 2 to 20, 3 to 20, 4 to 20, 5 to 20, and specifically 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0076] Remaining R 1 Preferred examples for this are particularly glycerol-based polyether radicals, C3-C18 hydroxyl-group-substituted polyether radicals, and C1-C8 linear alkyl or alkylene groups.

[0077] Here, the term polyether specifically includes poly(alkylene oxide)-derived compounds, wherein the alkylene group of the repeating unit is independently selected from C1-C8 alkylenes.

[0078] Remaining R 2 Preferred examples for are linear C1-C8 alkylene radicals, more preferably ethylene, propylene, butylene, pentylene, hexylene and heptylene, most preferably propylene and hexylene.

[0079] Remaining R 3 , R 4 and R 5 A preferred example of is a linear C1-C8 alkyl group and a linear alkyl group containing one or more moietyes of formula (III) or (IV), wherein m is preferably 2 to 6, and most preferably R 3 , R 4 and R 5 is independently selected from alkyl groups containing a methyl group and one or more moiety of formula (III).

[0080] R 6A preferred example of is a structure derived from a corresponding hydroxylcarboxylic acid by extraction of a carboxylate group and one OH group, wherein the hydroxylcarboxylic acid is preferably selected from ricinoleic acid, resquerolic acid, 10-hydroxyoctadecanoic acid, 12-hydroxyoctadecanoic acid, 14-hydroxytetradecanoic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or dihydroxycarboxylic acids, and in particular selected from polyhydroxycarboxylic acids that are 2,2'-di-hydroxymethylpropanoic acid, 9,10-dihydroxystearic acid, or particularly gluconic acid. Most preferably, R 6 It is derived from resquerolic acid or ricinoleic acid in the manner described above. In both cases, enantiomers of naturally occurring compounds, namely (9Z,12R)-12-hydroxyoctadex-9-enic acid obtained by saponification or fractional distillation of hydrolyzed castor oil, which is the seed oil of the castor plant, and (11Z,14R)-14-hydroxyicos-11-enic acid isolated from Paysonia and Physaria species, are particularly preferred. However, racemics, S enantiomers, as well as E-coordination isomers of the compound, racemics, enantiomers, and any possible mixtures thereof are also preferred according to the present invention.

[0081] R 11 Preferred examples for are C1-C10 alkyl groups, in particular methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentane and n-hexane groups, cyclopentyl and cyclohexane groups, C2-C10 alkenyl groups, in particular vinyl and allyl groups, and C6-C12 aromatic groups, in particular phenyl, tolyl and benzyl groups, each of which named herein may be substituted with a hydroxyl group or a halogen group.

[0082] According to the present invention, the counterion A of the ammonium ion according to the present invention -It is selected from monovalent to trivalent inorganic anions or monovalent to 30,000, preferably monovalent to 1,000, organic anions.

[0083] Here, the counteranion A - is preferably a halogenated anion such as chloride, bromide, and iodide; an inorganic oxoate anion such as sulfate and phosphate, phosphonate, sulfonate, and methosulfate; a carboxylate anion such as acetate, propionate, lactate, octanoate, 2-ethyl-hexanoate, dodecanoate, hexadecanoate, octadetanooate, oleate, ricinoleate, 12-hydroxy-octadecanoate, succinate, maleate, tartate, and polyethercarboxylate, 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 Selected from fatty acid carboxylate polymers of the type,

[0084] Here, R 1 or at least one R 7 One of them, or R 1 and at least one R 7 It has one or more carboxylate groups,

[0085] Preferably X = O, and

[0086] especially

[0087] -OC(O)-R 6 (-XC(O)-R 6 ) m-1 -XC(O)-R 7 , preferably -OC(O)-R 6 -(OC(O)-R 6 ) m-OC(O)-R 7 And,

[0088] That is, derived from a linear poly fatty acid structure as shown below, and

[0089]

[0090]

[0091] It is a branched linear fatty acid carboxylate polymer, and

[0092] That is, derived from a branched poly fatty acid structure as shown below, and

[0093]

[0094] R =

[0095]

[0096] R =

[0097]

[0098] R =

[0099]

[0100] or R =

[0101]

[0102] Or, as below, a branched linear fatty acid carboxylate polymer derived from castor oil or lesquerella oil and a partial ester of a polyfunctional carboxylic acid, particularly dicarboxylic acid succinic acid and maleic acid, and

[0103]

[0104] One R =

[0105]

[0106] The remaining 2 R elements =

[0107]

[0108] Fatty acid carboxylate dendritic polymer,

[0109] That is, derived from the dendritic poly fatty acid structure as shown below, and

[0110]

[0111] R =

[0112]

[0113] or XR 6 (-C(O)-XR 6 ) m-1 -C(O)-XR 7 or R 6 (-C(O)-XR 6 ) m-1 -C(O)-XR 7 It is a type, and

[0114] Here, in the two latter types, the R7 group possesses at least one carboxyl anion, and

[0115] Or R like the one below 1 [(-C(O)-X-R6) m -C(O)O - ] x It is a type, and

[0116]

[0117] Here, X, R 1 , R 6 , m and x are as defined above, and

[0118] R 7 is an optionally substituted straight-chain, cyclic or branched, saturated or unsaturated hydrocarbon radical having 1 to 36 carbon atoms, and -O-, -NH-, -C(O)-, -C(S)-, tertiary amino group ( ), quaternary ammonium group ( Optionally containing one or more groups selected from ), and may be substituted with OH groups or halogen groups, wherein radical R 7 It cannot contain internal carboxyl groups or amides, i.e., R 7It cannot contain a combination of -C(O)- groups and -O- groups or a combination of -C(O)- groups and -NH- or tertiary amino groups, and

[0119] Counterion A of this group - is preferably 1 to 5 valent, more preferably 1 to 10 valent, even more preferably 1 to 5 valent, most preferably 5 valent, 4 valent, 3 valent, 2 valent, or 1 valent anion, and

[0120] Or the counteranion is selected from the group consisting of carboxylate anions based on poly(acrylic acid) homo- and copolymers, and

[0121] That is, it is a carboxylate derived from a polyacrylic acid homopolymer as shown below, and

[0122]

[0123] Here, p = 2 to 10000, preferably 10 to 10000, more preferably 100 to 10000, even more preferably 1000 to 10000, and,

[0124] It is a carboxylate anion derived from a polyacrylic acid copolymer, and

[0125] That is, for example, it includes a non-reactive comonomer as follows, and

[0126]

[0127] a = 2 to 10000, preferably 10 to 10000, more preferably 100 to 10000, even more preferably 1000 to 10000, and,

[0128] b = 2 to 10,000, preferably 10 to 10,000, more preferably 100 to 10,000, even more preferably 1,000 to 10,000 (effective for all comonomers),

[0129] Here, the copolymer may have block or randomly distributed comonomer units, and

[0130] or a carboxylate anion derived from a polyacrylic acid copolymer containing a comonomer providing OH and amine functional groups, which can be functionalized particularly with a fatty acid or polyfatty acid through additional ester or amide bonds, e.g. as follows, and

[0131]

[0132] c = 2 to 10000, preferably 10 to 10000, more preferably 100 to 10000, even more preferably 1000 to 10000, and,

[0133] or a carboxylate anion derived from a polyacrylic acid copolymer containing a carboxylic acid functional group-containing comonomer, and

[0134] Here, the copolymer may have block or randomly distributed comonomer units, and

[0135] For example, as follows,

[0136]

[0137] d = 2 to 10000, preferably 10 to 10000, more preferably 100 to 10000, even more preferably 1000 to 10000, and,

[0138] e = 2 to 10,000, preferably 10 to 10,000, more preferably 100 to 10,000, even more preferably 1,000 to 10,000 (effective for all comonomers),

[0139] In particular, it is a carboxylate based on a maleic acid copolymer derived from a maleic anhydride copolymer, and

[0140] Here, the copolymer may have block or randomly distributed comonomer units, and

[0141] For example, as follows,

[0142]

[0143] f = 2 to 10,000, preferably 10 to 10,000, more preferably 100 to 10,000, even more preferably 1,000 to 10,000 (effective for all comonomers), and

[0144] g = 2 to 10,000, preferably 10 to 10,000, more preferably 100 to 10,000, even more preferably 1,000 to 10,000, and

[0145] It is a carboxylate based on poly(itaconic acid) homopolymers and copolymers, and

[0146] That is, derived from the following polyitaconic acid homopolymer, and

[0147]

[0148] h = 2 to 10000, preferably 10 to 10000, more preferably 100 to 10000, even more preferably 1000 to 10000, and,

[0149] Or derived from polyitaconic acid copolymer,

[0150] That is, containing a non-reactive comonomer,

[0151] Here, the copolymer may have block or randomly distributed comonomer units, and

[0152] For example, as follows,

[0153]

[0154] i = 2 to 10,000, preferably 10 to 10,000, more preferably 100 to 10,000, even more preferably 1,000 to 10,000 (effective for all comonomers),

[0155] j = 2 to 10000, preferably 10 to 10000, more preferably 100 to 10000, even more preferably 100 to 10000, and,

[0156] or derived from a polyitaconic acid copolymer containing a comonomer providing OH and amine functions, which can be functionalized through additional ester or amide bonds together with a fatty acid or polyfatty acid, e.g., 2-hydroxyethyl methacrylate-itaconic acid copolymer, and

[0157] or derived from a polyitaconic acid copolymer containing a carboxylic acid functional group containing a comonomer, and

[0158] Here, the copolymer may have block or randomly distributed comonomer units, and

[0159] For example, as follows,

[0160]

[0161] k = 2 to 10000, preferably 10 to 10000, more preferably 100 to 10000, even more preferably 1000 to 10000 (effective for all comonomers),

[0162] l = 2 to 10,000, preferably 10 to 10,000, more preferably 100 to 10,000, even more preferably 1,000 to 10,000, and

[0163] Here, the anion of this group is preferably 2 to 30,000 valent, more preferably 1 to 1,000 valent, even more preferably 10 to 10,000 valent, even more preferably 50 to 1,000 valent, and most preferably 100 to 1,000 valent anion.

[0164] According to the present invention, any cation structure according to the present invention can be combined with any anion according to the present invention.

[0165] It is desirable to combine a cation containing a small number of quaternary nitrogen atoms, namely 1 to 20, particularly 1 to 10, more specifically 1 to 6, and even more specifically 1 or 2 quaternary nitrogen atoms, with a monovalent to devalent anion, preferably a monovalent to hexavalent anion, more preferably a monovalent to trivalent anion, and even more preferably a monovalent anion or a divalent anion.

[0166] Optionally, polyanions of 11 to 30,000 valence, in particular polyanions of 11 to 100 valence or polyanions of 101 to 1,000 valence may be used.

[0167] Polyquaternary cations containing 21 or more quaternary nitrogen atoms are generally combined with lower valence counterions, namely monovalent to 50-valence anions, more preferably monovalent to 10-valence anions, even more preferably monovalent to 5-valence anions, most preferably monovalent and divalent counterions, in particular chloride anions, monocarboxylate and dicarboxylate anions. Here, the use of anions with a valence of 50 or higher is less preferred.

[0168] As used above, R 7 is independently selected from optionally substituted straight-chain, cyclic or branched, saturated or unsaturated hydrocarbon radicals having 1 to 36 carbon atoms, which are -O-, -NH-, -C(O)-, -C(S)-, tertiary amino groups ( ), quaternary ammonium group ( Optionally containing one or more groups selected from ), and may be substituted with OH groups or halogen groups, wherein radical R 7 It cannot contain internal carboxyl groups or amides, 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.

[0169] According to the present invention, radical R 7 It may be the same or different and may be selected from optionally substituted linear, cyclic or branched, saturated or unsaturated hydrocarbon radicals having 1 to 36 carbon atoms, and thus may be represented by a hydrocarbyl group selected from the group consisting of linear, branched or cyclic alkyl groups, linear, branched or cyclic alkenyl groups, linear, branched or cyclic alkynyl groups, linear, branched or cyclic alkalyl groups, linear, branched or cyclic aralkyl groups and, for example, linear, branched or cyclic aryl groups having 6 to 24 carbon atoms, particularly phenyl, benzyl or tolyl, and each optionally contains one or more functional groups as indicated above.

[0170] More preferably, R 7 The radical is selected from linear alkyl groups and linear alkenyl groups, in particular selected from linear C6-C24 alkyl groups such as hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecylene, nonadecyl, eicosyl, henicosyl, doicosyl, tricosyl, and tetraicosyl, or selected from linear C6-C24 alkenyl groups such as hexenyl, heptenyl, octenyl, nonenyl, desenyl, undesenyl, hexadecenyl, tridecenyl, tetradecenyl, octadecenyl, nonadecenyl, eicosenyl, henicosyl, doicosenyl, tricosenyl, and tetraicosenyl, wherein the group is most preferably a C(O) group or X adjacent by a terminal C-atom It is combined with the energy.

[0171] Adjacent C(O) or X and R 7 There are no restrictions on the position of the C-atom of the hydrocarbyl radical to which this combines.

[0172] However, R 7is preferably derived from a carboxylic acid or hydroxycarboxylic acid having one or more hydroxyl groups, more preferably from a carboxylic acid or monohydroxycarboxylic acid, and most preferably from a C7-C25 fatty acid that does not possess a hydroxyl group as a substituent. Thus, R 7 is preferably represented by the alkyl or alkenyl chain of such carboxylic acid. For example, R 7 In the case of this derived from ricinoleic acid

[0173]

[0174] R 7 ...represents the 11-hydroxyheptadex-8-enyl radical, and

[0175]

[0176] or R 7 In the case of this derived from oleic acid,

[0177]

[0178] R 7 It represents the heptadex-8-enyl radical.

[0179]

[0180] R 7A preferred example is a structure derived from a corresponding carboxylic acid or hydroxycarboxylic acid by extraction of a carboxylate group, wherein the carboxylic acid is selected from acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enantic acid, caprylic acid, pellagonal acid, capric acid, undecanal acid, lauric acid, tridecanoic acid, myristic acid, pentadecanal acid, palmitic acid, margaric acid, stearic acid, linoleic acid, α-linolenic acid, η-linolenic acid, nonadecylic acid, arachidonic acid, midic acid, arachidonic acid, heneicosanic acid, docosanic acid, tricosylic acid, and lignoceric acid, and resquerolic acid, ricinoleic acid, 10-hydroxyoctadecanoic acid, 12-hydroxyoctadecanoic acid, 14-hydroxy It is selected from hydroxyl carboxylic acids such as tetradecanoic acid, 10-hydroxy stearic acid, and 12-hydroxy stearic acid, or in particular from dihydroxy carboxylic acids such as 2,2'-di-hydroxymethylpropanoic acid and 9,10-dihydroxy stearic acid, or in particular from polyhydroxy carboxylic acids such as gluconic acid.

[0181] Radical R 7 -O-, -NH-, -C(O)-, -C(S)-, tertiary amino group( ), quaternary ammonium group ( It may optionally include one or more groups selected from ), but may be substituted with OH groups or halogen groups, and radical R 7 It cannot contain a combination of -C(O)- groups and -O- groups forming an internal carboxylate 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.

[0182] Structure of chemical formulas (I) and (II) and R 1 , R 2 , R 3 , R 4 and R 5Considering the definition, some substructures of the compound given according to the present invention are represented by chemical formulas (I) and (II), and the residue R defined above in one or more ways 1 , R 2 , R 3 , R 4 and R 5 It is evident that it can be assigned to.

[0183] Only in such cases shall the following rule apply to the above term R 1 -R 5 Regarding this, it is applied for the allocation of substructures in a clear manner in this order.

[0184] - R 1 is the subscript x, i.e., R 1 The number of -(-F) groups combined with should be selected in as many ways as possible;

[0185] - R 1 must be selected in such a way that the number of groups F with n ≠ 0 is as small as possible;

[0186] - If there are multiple options to satisfy the above requirements, R 1 R in as many ways as possible the number of carbon atoms 1 You must choose;

[0187] - If there are two or more substructures that satisfy the aforementioned requirements in the same way, R shall be the substructure with the highest sum of the atomic weights of the atoms contained in it among the possible substructures. 1 Select .

[0188] According to the present invention, residue R 2 , R 3 , R 4 , R 5 , R 6 or R 7 If any of the above are present in the compound according to the present invention, each residue may exist in another substructure as defined above, i.e., each R 2 , R3 , R 4 , R 6 and R 7 The device is independently selected according to the definition in accordance with the present invention.

[0189] In a preferred embodiment of the present invention, a compound of the following chemical formula as defined above is provided:

[0190] R 1 (-F) x (I)

[0191] Here, x is between 2 and 50.

[0192] More preferably, according to this embodiment, x is in the range of 3 to 50, 4 to 50, 5 to 50, 6 to 50, 7 to 50, 8 to 50, 9 to 50, 10 to 50, 2 to 40, 2 to 35, 2 to 30, 2 to 25, 2 to 20, 2 to 15, or 2 to 10.

[0193] In another preferred embodiment according to the present invention, in a compound of formula (I)

[0194] R 1 (-F) x (I)

[0195] As defined above, it does not contain poly(ethylene oxide) or poly(propylene oxide) units.

[0196] According to the present invention, the poly(ethylene oxide) unit has the chemical formula (CH2CH2O) where x ≥ 2 x Defined by units denoted as, and the poly(propylene oxide) unit is [CH2CH(CH3)O] with the chemical formula x ≥ 2. x It is defined as a unit indicated by.

[0197] In a further preferred embodiment according to the present invention, formula R 1 (-F) x (I) as defined above in the compound R 1contains at least one moiety of chemical formula (IIIa), or

[0198] (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa),

[0199] It contains at least one moiety of the chemical formula (IVa), and

[0200] (-C(O)-XR 6 ) m -C(O)-XR 7 (IVa)

[0201] Here, X and R 6 and m are as defined above, and

[0202] R 7 is independently selected from optionally substituted straight-chain, cyclic or branched, saturated or unsaturated hydrocarbon radicals having 1 to 36 carbon atoms, and -O-, -NH-, -C(O)-, -C(S)-, tertiary amino group ( ), quaternary ammonium group ( Optionally containing one or more groups selected from ), and may be substituted with an OH group or a halogen group, wherein radical R 7 It cannot contain internal carboxyl groups or amides, 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.

[0203] According to this embodiment, radical R 7It may be the same or different and may be selected from optionally substituted linear, cyclic or branched, saturated or unsaturated hydrocarbon radicals having 1 to 36 carbon atoms, and thus may be represented by a hydrocarbyl group selected from the group consisting of linear, branched or cyclic alkyl groups, linear, branched or cyclic alkenyl groups, linear, branched or cyclic alkynyl groups, linear, branched or cyclic alkalyl groups, linear, branched or cyclic aralkyl groups, and linear, branched or cyclic aryl groups having 6 to 24 carbon atoms, such as phenyl, benzyl or tolyl, and each optionally contains one or more functional groups as described above.

[0204] More preferably, R 7 The radical is selected from linear alkyl groups and linear alkenyl groups, in particular from linear C6-C24 alkyl groups such as hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecylene, nonadecyl, eicosyl, henicosyl, doicosyl, tricosyl, and tetraicosyl, or from linear C6-C24 alkenyl groups such as hexenyl, heptenyl, octenyl, nonenyl, desenyl, undesenyl, hexadecenyl, tridecenyl, tetradecenyl, octadecenyl, nonadecenyl, eicosyl, henicosyl, doicosyl, tricosyl, and tetraicosyl, wherein the group is most preferably bonded to an adjacent X group by a terminal C-atom.

[0205] Adjacent unit X and unit R 7 There are no restrictions on the position of the C-atom of this binding hydrocarbyl radical.

[0206] However, R 7 It is preferably derived from a carboxylic acid or hydroxycarboxylic acid having one or more hydroxyl groups, more preferably a carboxylic acid or monohydroxycarboxylic acid, and most preferably from a C7-C25 fatty acid that does not possess a hydroxyl group as a substituent. Thus, R7 is preferably R 7 As exemplified above, this represents the alkyl or alkenyl chain of such a carboxylic acid.

[0207] R according to this specific example 7 A preferred example is a structure derived from a corresponding carboxylic acid or hydroxycarboxylic acid by extraction of a carboxylate group, wherein the carboxylic acid may be selected from acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthine acid, caprylic acid, pelargonic acid, capric acid, undecanoic acid, lauric acid, tridecanoic acid, myristic acid, pentadecanoic acid, palmitic acid, margaric acid, stearic acid, linoleic acid, α-linolenic acid, η-linolenic acid, oleic acid, nonadecylic acid, arachidic acid, midic acid, arachidonic acid, heneicosanic acid, docosanic acid, tricosylic acid, and lignoceric acid, and resquerolic acid, ricinoleic acid, 10-hydroxyoctadecanoic acid, 12-hydroxyoctadecanoic acid, It may be selected from hydroxyl carboxylic acids such as 14-hydroxytetradecanoic acid, 10-hydroxystearic acid, and 12-hydroxystearic acid, or in particular from dihydroxycarboxylic acids such as 2,2'-di-hydroxymethylpropanoic acid and 9,10-dihydroxystearic acid, or in particular from polyhydroxycarboxylic acids such as gluconic acid.

[0208] More preferably, R according to this embodiment 7 Radicals are derived from palmitic acid, margaric acid, stearic acid, linoleic acid, α-linolenic acid, η-linolenic acid, oleic acid, nonadecylic acid, arachidic acid, 10-hydroxy stearic acid, 12-hydroxy stearic acid, ricinoleic acid, resquerolic acid, or 2,2'-dihydroxymethylpropanoic acid.

[0209] The most desirable R according to this embodiment 7 The radicals are oleic acid, stearic acid, resquerolic acid, and ricinoleic acid.

[0210] Radical R 7-O-, -NH-, -C(O)-, -C(S)-, tertiary amino group( ), quaternary ammonium group ( It may optionally include one or more groups selected from ), but may be substituted with OH groups or halogen groups, and radical R 7 It cannot contain a combination of -C(O)- and -O- groups forming an internal carboxylate group, i.e., an internal ester group or an internal amide group, or a combination of -C(O)- and -NH- or tertiary amino groups.

[0211] In another preferred embodiment according to the present invention, formula R 1 (-F) x (I) of the compound

[0212] As defined above, residue R 1 or R 2 Only one or more of them contains one or more moieties of chemical formula (III) or (IV), and

[0213] (-XC(O)-R 6 ) m -XC(O)- (III) or

[0214] (-C(O)-XR 6 ) m -C(O)-X- (IV),

[0215] Preferably residue R 1 or R 2 Only one or more of them contains one or more moieties of formula (IIIa) or formula (IVa), and

[0216] (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa),

[0217] (-C(O)-XR 6 ) m -C(O)-XR 7 (IVa),

[0218] Here, X, R 6 , R7 and m are as defined above.

[0219] According to this embodiment, preferably, residue R 1 or R 2 In the moiety of the chemical formula (IIIa) or (Iva),

[0220] X=O and,

[0221] R 6 is optionally independently selected from hydroxyl-substituted hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, doicosylene, tricosylene, and tetraicosylene, or hexenylene, heptenylene, octenylene, nonenylene, desenylene, undesenylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, doicosylene, tricosylene, tetraicosylene, where this The groups are most preferably bonded to adjacent C(O) groups by terminal C-atoms, and

[0222] R 7 is optionally independently selected from hydroxyl-substituted hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, henicosyl, doicosyl, tricosyl and tetraicosyl, or hexenyl, heptenyl, octenyl, nonenyl, desenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosyl, henicosyl, doicosyl, tricosyl and tetraicosyl, wherein these groups are most preferably bonded to an adjacent C(O) group by a terminal C-atom, and

[0223] m is 1 to 10, preferably 1, 2, 3, 4 or 5.

[0224] Even more preferably, it is XO, and

[0225] R 6 is selected from hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, hexadecenylene, heptadecylene, octadecylene, nonadecylene, and eicosylene, and

[0226] R 7 is selected from hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, hexadecenyl, heptadecyl, octadecyl, nonadecyl, and eicosyl, and

[0227] m is 1, 2, 3, 4, or 5.

[0228] Most preferably in these embodiments,

[0229] X = O and,

[0230] R 6 It is derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or resquerolic acid, and

[0231] R 7 It is derived from oleic acid, ricinoleic acid, or stearic acid, and

[0232] m is 1, 2, 3, 4, or 5.

[0233] In another preferred embodiment according to the present invention, in the formula R as defined above, 1 (-F) xIn the compound of (I), at least 1% of all F groups contains at least one moiety of formula (III) or (IV), more preferably at least 10% of all F groups contains at least one moiety of formula (III) or (IV), even more preferably at least 50% of all F groups contains at least one moiety of formula (III) or (IV), most preferably 100% of all F groups contains at least one moiety of formula (III) or (IV), or at least 1% of all F groups contains at least one moiety of formula (IIIa) or (IVa), more preferably at least 10% of all F groups contains at least one moiety of formula (IIIa) or (IVa), even more preferably at least 50% of all F groups contains at least one moiety of formula (IIIa) or (IVa), and most preferably 100% of all F groups contains at least one moiety of formula (IIIa) or (IVa). It contains one moiety.

[0234] According to this embodiment, preferably, each moiety of formula (III) or (IV) of the F group is optionally hydroxyl-substituted hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, doicosylene, tricosylene and tetraicosylene, or hexenylene, heptenylene, octenylene, nonenylene, decenylene, undecenylene, dodecylene, octadecenylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecenylene, octadecenylene, nonadecenylene, eicosylene, At least one R selected from henicosenylene, doicosenylene, tricosenylene, and tetraicosenylene 6 Contains,

[0235] More preferably, each moiety of formula (III) or (IV) of the F group is at least one R selected from optionally hydroxyl-substituted hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, hexadecenylene, heptadecylene, octadecylene, nonadecylene, and eicosylene. 6 Contains,

[0236] m is 1, 2, 3, 4, or 5, and most preferably R in each moiety of formula (III) or (IV) of the F group 6 It is derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or resquerolic acid, and

[0237] m is 1, 2, 3, 4, or 5.

[0238] In another preferred embodiment according to the present invention, in the formula R as defined above, 1 (-F) x In compound (I), all R 2 At least 1% of the group contains at least one moiety of formula (III) or (IV), and more preferably all R 2 At least 10% of the group contains at least one moiety of formula (III) or (IV), and more preferably all R 2 At least 50% of the group contains at least one moiety of formula (III) or (IV), most preferably all R 2 100% of the group contains at least one moiety of formula (III) or (IV), or all R 2 At least 1% of the group contains at least one moiety of formula (IIIa) or (IVa), and more preferably all R 2 At least 10% of the group contains at least one moiety of formula (IIIa) or (IVa), and more preferably all R 2At least 50% of the group contains at least one moiety of formula (IIIa) or (IVa), most preferably all R 2 100% of the group contains at least one moiety of chemical formula (IIIa) or (IVa).

[0239] According to this embodiment, preferably R 2 Each moiety of the chemical formula (III) or (IV) of the group is optionally hydroxyl-substituted hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, doicosylene, tricosylene and tetraicosylene, or hexenylene, heptenylene, octenylene, nonenylene, decenylene, undecenylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, doicosylene, tricosylene and At least one R selected from tetraicosenylene 6 Contains,

[0240] More preferably R 2 Each moiety of the chemical formula (III) or (IV) of the group is at least one R selected from optionally hydroxyl-substituted hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, hexadecenylene, heptadecylene, octadecylene, nonadecylene, and eicosylene. 6 Contains,

[0241] m is 1, 2, 3, 4, or 5, and

[0242] Most preferably R 2 R in each moiety of the chemical formula (III) or (IV) of the group 6 It is derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or resquerolic acid, and

[0243] m is 1, 2, 3, 4, or 5.

[0244] In another preferred embodiment according to the present invention, in the formula R as defined above, 1 (-F) x In compound (I), all R 3 , R 4 and R 5 At least 1% of the group contains at least one moiety of formula (III) or (IV), and more preferably all R 3 , R 4 and R 5 At least 10% of the group contains at least one moiety of formula (III) or (IV), and more preferably all R 3 , R 4 and R 5 At least 50% of the group contains at least one moiety of formula (III) or (IV), most preferably all R 3 , R 4 and R 5 100% of the group contains at least one moiety of formula (III) or (IV), or all R 3 , R 4 and R 5 At least 1% of the group contains at least one moiety of formula (IIIa) or (IVa), and more preferably all R 3 , R 4 and R 5 At least 10% of the group contains at least one moiety of formula (IIIa) or (IVa), and more preferably all R 3 , R 4 and R 5 At least 50% of the group contains at least one moiety of formula (IIIa) or (IVa), most preferably all R 3 , R 4 and R 5 100% of the group contains at least one moiety of chemical formula (IIIa) or (IVa).

[0245] According to this embodiment, preferably R 3 , R 4 and R 5 Each moiety of the chemical formula (III) or (IV) of the group is optionally a hydroxyl-substituted hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, doicosylene, tricosylene and tetraicosylene, or hexenylene, heptenylene, octenylene, nonenylene, decenylene, undecenylene, dodecylene, octadecenylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecenylene, octadecenylene, nonadecenylene, eicosylene, henicosylene, doicosylene, At least one R selected from tricosenylene and tetraicosenylene 6 Contains,

[0246] More preferably R 3 , R 4 and R 5 Each moiety of the chemical formula (III) or (IV) of the group is at least one R selected from optionally hydroxyl-substituted hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, hexadecenylene, heptadecylene, octadecylene, nonadecylene, and eicosylene. 6 Contains,

[0247] m is 1, 2, 3, 4, or 5, and

[0248] Most preferably R 3 , R 4 and R 5 R in each moiety of the chemical formula (III) or (IV) of the group 6 It is derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or resquerolic acid, and

[0249] m is 1, 2, 3, 4, or 5.

[0250] In another preferred embodiment according to the present invention, in the formula R as defined above, 1 (-F) x In the compound (I),

[0251] x is 2, and the compound is the following chemical formula (V):

[0252]

[0253] Here, R 1 , R 2 , R 3 , R 4 , R 5 and n are as defined above.

[0254] In a preferred embodiment of the present invention, the formula R as defined above. 1 (-F) x It is a compound of (I), and

[0255] Here, R 1 The radical is selected from optionally substituted hydrocarbon radicals having 1 to 50 valence, which has up to 1000 carbon atoms, preferably 2 to 300 carbon atoms, more preferably 3 to 200 carbon atoms, even more preferably 3 to 150 carbon atoms, specifically 3 to 50 carbon atoms, more specifically 3 to 20 carbon atoms, -O-, -NH-, -C(O)-, -C(S)-, tertiary amino group ( It may optionally contain one or more groups from ), may be substituted with -OH groups and halogen groups, and preferably R 1 is a C3-C18 glycerol-based polyether radical or a C1-C8 linear alkylene radical, and

[0256] F has the chemical formula (VI), which corresponds to the chemical formula (II) where n is 0, and

[0257]

[0258] F giga R 1 Bonded to the carbon atoms of,

[0259] Here

[0260] R 3 , R 4 , R 5 is independently selected from hydrogen and optionally substituted straight-chain, cyclic or branched, saturated, unsaturated, or aromatic hydrocarbon radicals, which have up to 300 carbon atoms, preferably 1 to 200 carbon atoms, more preferably 1 to 150 carbon atoms, even more preferably 1 to 50 carbon atoms, specifically 1 to 20 carbon atoms, more specifically 1 to 10 carbon atoms, -O-, -NH-, -C(O)-, -C(S)-, tertiary amino group ( ), quaternary ammonium group ( Optionally containing one or more groups selected from ), can be substituted with OH, and preferably R 3 to R 5 is a C1-C8 linear alkyl group such as methyl, ethyl, propyl or butyl, or a linear alkyl group containing one or more moietyes of formula (III) or (IV), more preferably a linear alkyl group terminated by a group of formula (IIIa) or (IVa), and

[0261] Counterion A - is selected from monovalent to trivalent inorganic anions and monovalent to 30,000, preferably monovalent to 1,000, organic anions, and preferably halogenated anions such as chloride, bromide, iodide, sulfate, phosphate, phosphonate, sulfonate, methosulfate, acetate, propionate, lactate, octanoate, 2-ethyl-hexanoate, dodecanoate, hexadecanoate, octadecanoate, oleate, ricinoleate, 12-hydroxy-octadecanoate, succinate, maleate, tartrate, polyethercarboxylate, R1[(-C(O)-XR 6 ) m -C(O)-XR 7 ]x or R 1 [(XC(O)-R 6 ) m -XC(O)-R 7 ] x It is a carboxylate anion such as a fatty acid carboxylate polymer of the type, and

[0262] Here, R 1 or at least one R 7 One of them, or R 1 and at least one R 7 It has one or more carboxylate groups,

[0263] Preferably X = O, and

[0264] especially

[0265] - Fatty acid carboxylate linear polymer type

[0266] -OC(O)-R 6 (-XC(O)-R 6 ) m-1 -XC(O)-R 7 , preferably

[0267] -OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7 ,

[0268] That is, derived from a linear polyfatty acid structure,

[0269] - Branched linear polymer of fatty acid carboxylates,

[0270] That is, derived from a branched polyfatty acid structure,

[0271] It is a branched linear polymer of fatty acid carboxylates derived from castor oil or lesquerella oil, and part esters of polyfunctional carboxylic acids, particularly dicarboxylic acids succinic acid and maleic acid, and, for example

[0272]

[0273] One R =

[0274]

[0275] The remaining 2 R =

[0276]

[0277] - Fatty acid carboxylate dendritic polymer,

[0278] That is, dentritic poly fatty acid structure, or XR 6 (-C(O)-XR 6 ) m-1 -C(O)-XR 7 or R 6 (-C(O)-XR 6 ) m-1 -C(O)-XR 7 Derived from the type,

[0279] R in the two latter types 7 The group is at least one anionic carboxylate group, or R 1 [(-C(O)-X-R6) m -C(O)O - ] x Possessing the type,

[0280] X, R 1 , R 6 , R 7 , m and x are as defined above, and

[0281] Here, the counterion A of this group - is preferably 1 to 50 valent, more preferably 1 to 10 valent, even more preferably 1 to 5 valent, most preferably 5 valent, 4 valent, 3 valent, 2 valent, or 1 valent anion, and

[0282] Or the counteranion is selected from the group consisting of carboxylate anions based on poly(acrylic acid) homo- and copolymers, and

[0283] That is, carboxylates derived from polyacrylic acid homopolymers,

[0284]

[0285] Here, p = 2 to 10000, preferably 10 to 10000, more preferably 100 to 10000, even more preferably 1000 to 10000, and,

[0286] Carboxylate anion derived from polyacrylic acid copolymer,

[0287] That is, it includes a non-reactive comonomer, for example as follows, and

[0288]

[0289] a = 2 to 10000, preferably 10 to 10000, more preferably 100 to 10000, even more preferably 1000 to 10000, and,

[0290] b = 2 to 10,000, preferably 10 to 10,000, more preferably 100 to 10,000, even more preferably 1,000 to 10,000 (effective for all comonomers),

[0291] Here, the copolymer may have block or randomly distributed comonomer units, and

[0292] or a carboxylate anion derived from a polyacrylic acid copolymer containing a comonomer providing OH and amine functional groups that can be functionalized, particularly through a fatty acid or polyfatty acid and additional ester or amide bonds, e.g., as follows

[0293]

[0294] c = 2 to 10000, preferably 10 to 10000, more preferably 100 to 10000, even more preferably 1000 to 10000, and,

[0295] or a carboxylate anion derived from a polyacrylic acid copolymer containing a carboxylic acid functional group-containing comonomer,

[0296] Here, the copolymer may have block or randomly distributed comonomer units, and

[0297] For example, as follows

[0298]

[0299] d = 2 to 10000, preferably 10 to 10000, more preferably 100 to 10000, even more preferably 1000 to 10000, and,

[0300] e = 2 to 10,000, preferably 10 to 10,000, more preferably 100 to 10,000, even more preferably 1,000 to 10,000 (effective for all comonomers),

[0301] In particular, a carboxylate having a maleic acid copolymer as a substrate derived from a maleic anhydride copolymer,

[0302] Here, the copolymer may have block or randomly distributed comonomer units, and

[0303] For example, as follows,

[0304]

[0305] f = 2 to 10,000, preferably 10 to 10,000, more preferably 100 to 10,000, even more preferably 1,000 to 10,000 (effective for all comonomers),

[0306] g = 2 to 10,000, preferably 10 to 10,000, more preferably 100 to 10,000, even more preferably 1,000 to 10,000, and

[0307] Carboxylates based on poly(itaconic acid) homopolymers and copolymers,

[0308] That is, derived from polyitaconic acid homopolymer,

[0309]

[0310] h = 2 to 10000, preferably 10 to 10000, more preferably 100 to 10000, even more preferably 1000 to 10000, and,

[0311] or derived from a poly(itaconic acid) copolymer,

[0312] That is, containing a non-reactive comonomer,

[0313] Here, the copolymer may have block or randomly distributed comonomer units, and

[0314] For example, as follows,

[0315]

[0316] i = 2 to 10,000, preferably 10 to 10,000, more preferably 100 to 10,000, even more preferably 1,000 to 10,000 (effective for all comonomers),

[0317] j = 2 to 10000, preferably 10 to 10000, more preferably 100 to 10000, even more preferably 1000 to 10000, and,

[0318] or derived from a polyitaconic acid copolymer containing a comonomer providing OH and amine functions that can be functionalized, particularly through a fatty acid or polyfatty acid and additional ester or amide bonds, e.g., a 2-hydroxyethyl methacrylate-itaconic acid copolymer, and

[0319] or derived from a polyitaconic acid copolymer containing a carboxylic acid functional group containing a comonomer, and

[0320] Here, the copolymer may have block or randomly distributed comonomer units, and

[0321] For example, as follows

[0322]

[0323] k = 2 to 10000, preferably 10 to 10000, more preferably 100 to 10000, even more preferably 1000 to 10000 (effective for all comonomers),

[0324] l = 2 to 10,000, preferably 10 to 10,000, more preferably 100 to 10,000, even more preferably 1,000 to 10,000, and

[0325] Here, the anion of this group is preferably divalent to 30,000 valent, more preferably divalent to 1,000 valent, even more preferably 10 valent to 1,000 valent, even more preferably 50 valent to 1,000 valent, and most preferably 100 valent to 1,000 valent anion, and

[0326] However, radical R of the cation structure of chemical formulas (I) and (II) 1 , R 3 , R 4 , R 5 At least one of them contains at least one moiety of chemical formula (IIIa) or (IVa).

[0327] (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa)

[0328] (-C(O)-XR 6 ) m -C(O)-XR 7 (IVa)

[0329] Here, X is as defined above, and

[0330] m = 1 to 20, preferably 1 to 10, more preferably 1 to 6, even more preferably 2 to 6, specifically 1, 2, 3, 4, 5, 6, and

[0331] R 11 It is preferably hydrogen, n-, iso-, or tert.-C1-C 22 -alkyl, C2-C22 -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 Selected from the group consisting of -alkenyloxyalkyl, which may optionally be substituted with hydroxyl and halogen, respectively, and may optionally contain one or more ether groups (-O-), preferably hydrogen or n-, iso-, or tert.-C1-C 22 - It is alkyl, and

[0332] R 6 is independently selected from optionally substituted straight-chain, cyclic, or branched, saturated or unsaturated hydrocarbon radicals, which have 1 to 36 carbon atoms, preferably 1 to 24 carbon atoms, more preferably 1 to 18 carbon atoms, even more preferably 8 to 18 carbon atoms, preferably R 6 is a C6 to C24 linear alkylene or alkenylene group, most preferably derived from ricinoleic acid or resquerolic acid, and

[0333] R 7 is independently selected from optionally substituted straight-chain, cyclic or branched, saturated or unsaturated hydrocarbon radicals, which have 1 to 36 carbon atoms, preferably 1 to 24 carbon atoms, more preferably 1 to 18 carbon atoms, even more preferably 8 to 18 carbon atoms, -O-, -NH-, -C(O)-, -C(S)-, tertiary amino groups ( ), quaternary ammonium group ( Optionally comprising one or more groups selected from ), which may be substituted with OH groups or halogen groups, wherein radical R 7It may not include a combination of -C(O)- and -O- groups forming an internal carboxylate group or an internal amide group, or a combination of -C(O)- and -NH- or tertiary amino groups, and preferably R 7 is a C6 to C24 alkyl or alkenyl group, more preferably a linear C12 to C24 alkyl or C12 to C24 alkenyl group, most preferably derived from linoleic acid, linolenic acid, or oleic acid, and

[0334] However, at least one R 6 It has more than 6 carbon atoms, and

[0335] For x = 1

[0336] R 1 , R 3 , R 4 , R 5 It does not bond to the nitrogen atom of the group below through -OCH2CH2-.

[0337]

[0338] In a further preferred embodiment of the present invention, formula R 1 (-F) x Compound of (I) is provided,

[0339] Here, R 1 The radical is selected from optionally substituted hydrocarbon radicals having 1 to 50 valence, preferably 1 to 30 valence, more preferably 1 to 22 valence, even more preferably 1 to 10 valence, specifically 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10 valence, which have up to 1000 carbon atoms, preferably 2 to 300 carbon atoms, more preferably 3 to 200 carbon atoms, even more preferably 3 to 150 carbon atoms, specifically 3 to 50 carbon atoms, even more specifically 3 to 20 carbon atoms, and -O-, -NH-, -C(O)-, -C(S)-, tertiary amino group ( ), quaternary ammonium group It may optionally contain one or more groups selected from and may be substituted with -OH,

[0340] F has the chemical formula (VI),

[0341]

[0342] F is R 1 Bonded to the carbon atoms of,

[0343] Here

[0344] R 3 , R 4 , R 5 is an optionally substituted straight-chain, cyclic or branched, saturated, unsaturated, or aromatic hydrocarbon radical, having up to 300 carbon atoms, preferably 1 to 200 carbon atoms, more preferably 1 to 150 carbon atoms, even more preferably 1 to 50 carbon atoms, specifically 1 to 20 carbon atoms, more specifically 1 to 10 carbon atoms, and -O-, -NH-, -C(O)-, -C(S)-, tertiary amino group ( ), quaternary ammonium group ( Optionally containing one or more groups selected from ), and may be substituted with OH,

[0345] Counterion A - is selected from monovalent to trivalent inorganic anions and monovalent to 30,000valent, particularly monovalent to 1,000valent organic anions, preferably halogenated anions such as chloride, bromide, iodide, sulfate, phosphate, phosphonate, sulfonate, methosulfate, acetate, propionate, lactate, octanoate, 2-ethyl-hexanoate, dodecanoate, hexadecanoate, octadecanoate, oleate, ricinoleate, 12-hydroxy-octadecanoate, succinate, maleate, tartrate, polyethercarboxylate, R 1 [(-C(O)-XR6 ) m -C(O)-XR 7 ] x or R 1 [(XC(O)-R 6 ) m -XC(O)-R 7 ] x Selected from carboxylate anions such as the type of fatty acid carboxylate polymer type, and

[0346] Here, R 1 or at least one R 7 One of them, or R 1 and at least one R 7 It has one or more carboxylate groups,

[0347] Preferably X = O, and

[0348] especially

[0349] - - OC(O)-R 6 (-XC(O)-R 6 ) m-1 -XC(O)-R 7 , preferably - OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7 Type of fatty acid carboxylate linear polymer

[0350] That is, derived from a linear polyfatty acid structure,

[0351] - Fatty acid carboxylate molecules linear polymers,

[0352] That is, it is a branched linear polymer of fatty acid carboxylates derived from a branched poly fatty acid structure, particularly a partial ester of a polyfunctional carboxylic acid, specifically dicarboxylic acid succinic acid and maleic acid, and derived from castor oil or lesquerella oil, e.g., as follows

[0353]

[0354] One R =

[0355]

[0356] The remaining 2 R =

[0357]

[0358] - Fatty acid carboxylate dendritic polymer,

[0359] That is, dendritic poly fatty acid structure, or XR 6 (-C(O)-XR 6 ) m-1 -C(O)-XR 7 or R 6 (-C(O)-XR 6 ) m-1 -C(O)-XR 7 Derived from the type,

[0360] Here, R in the two latter types 7 The group has one or more anionic carboxylate groups, and

[0361] or R 1 [(-C(O)-X-R6) m -C(O)O - ] x Derived from the type,

[0362] Here, X, R 1 , R 6 , R 7 , m and x are as defined above, and

[0363] Counterion A of this group - is preferably 1 to 50 valent, more preferably 1 to 10 valent, even more preferably 1 to 5 valent, most preferably 5 valent, 4 valent, 3 valent, 2 valent, or 1 valent anion, and

[0364] Or the counterion is selected from the group consisting of carboxylate anions based on poly(acrylic acid) homo- and copolymers, and

[0365] That is, it is a carboxylate derived from a polyacrylic acid homopolymer, and

[0366]

[0367] Here, p = 2 to 10000, preferably 10 to 10000, more preferably 100 to 10000, even more preferably 1000 to 10000, and,

[0368] It is a carboxylate anion derived from a polyacrylic acid copolymer, and

[0369] That is, it includes a non-reactive comonomer, for example as follows

[0370]

[0371] a = 2 to 10000, preferably 10 to 10000, more preferably 100 to 10000, even more preferably 1000 to 10000, and,

[0372] b = 2 to 10,000, preferably 10 to 10,000, more preferably 100 to 10,000, even more preferably 1,000 to 10,000 (effective for all comonomers),

[0373] Here, the copolymer may have block or randomly distributed comonomer units, and

[0374] or a carboxylate anion derived from a polyacrylic acid copolymer containing a comonomer providing OH and amine functional groups that can be functionalized via additional ester or amide bonds with a fatty acid or polyfatty acid, in particular, and is, for example, as follows

[0375]

[0376] c = 2 to 10000, preferably 10 to 10000, more preferably 100 to 10000, even more preferably 1000 to 10000, and,

[0377] or a carboxylate anion derived from a polyacrylic acid copolymer containing a carboxylic acid functional group-containing comonomer, and

[0378] Here, the copolymer may have block or randomly distributed comonomer units, and

[0379] For example, as follows

[0380]

[0381] d = 2 to 10000, preferably 10 to 10000, more preferably 100 to 10000, even more preferably 1000 to 10000, and,

[0382] e = 2 to 10,000, preferably 10 to 10,000, more preferably 100 to 10,000, even more preferably 1,000 to 10,000 (effective for all comonomers),

[0383] In particular, it is a carboxylate based on a calecoxylate derived from a maleic anhydride copolymer, and

[0384] Here, the copolymer may have block or randomly distributed comonomer units, and

[0385] For example, as follows

[0386]

[0387] f = 2 to 10,000, preferably 10 to 10,000, more preferably 100 to 10,000, even more preferably 1,000 to 10,000 (effective for all comonomers),

[0388] g = 2 to 10,000, preferably 10 to 10,000, more preferably 100 to 10,000, even more preferably 1,000 to 10,000, and

[0389] It is a carboxylate based on poly(itaconic acid) homopolymers and copolymers, and

[0390] That is, derived from polyitaconic acid homopolymer, and

[0391]

[0392] h = 2 to 10000, preferably 10 to 10000, more preferably 100 to 10000, even more preferably 1000 to 10000, and,

[0393] Or derived from polyitaconic acid copolymer,

[0394] That is, containing a non-reactive comonomer,

[0395] Here, the copolymer may have block or randomly distributed comonomer units, and

[0396] For example, as follows

[0397]

[0398] i = 2 to 10,000, preferably 10 to 10,000, more preferably 100 to 10,000, even more preferably 1,000 to 10,000 (effective for all comonomers),

[0399] j = 2 to 10000, preferably 10 to 10000, more preferably 100 to 10000, even more preferably 1000 to 10000, and,

[0400] or derived from a polyitaconic acid copolymer containing a comonomer providing OH and amine functions that can be functionalized, particularly through additional ester or amide bonds with a fatty acid or polyfatty acid, e.g., a 2-hydroxyethyl methacrylate-itaconic acid copolymer, and

[0401] or derived from a polyitaconic acid copolymer containing a carboxylic acid functional group containing a comonomer, and

[0402] Here, the copolymer may have block or randomly distributed comonomer units, and

[0403] For example, as follows

[0404]

[0405] k = 2 to 10000, preferably 10 to 10000, more preferably 100 to 10000, even more preferably 1000 to 10000 (effective for all comonomers),

[0406] l = 2 to 10,000, preferably 10 to 10,000, more preferably 100 to 10,000, even more preferably 1,000 to 10,000, and

[0407] Here, the anion of this group is preferably a divalent to 30,000 valent, more preferably a divalent to 1,000 valent, even more preferably a devalent to 1,000 valent, and most preferably a 100 valent to 1,000 valent anion, and

[0408] However, radical R of the cation structure of chemical formulas (I) and (II) 1 , R 3 , R 4 , R 5 At least one of them contains at least one moiety of chemical formula (VII) or (VIII), and

[0409] -XC(O)-R x -(XC(O)-R x ) m-1 -XC(O)-R 7 (VII) 또는

[0410] -XC(O)-R x -(XC(O)-R x ) m -XC(O)-R 7 (VIII)

[0411] Here

[0412] X is O or NR 11 And,

[0413] m = 1 to 20, preferably 1 to 10, more preferably 1 to 6, even more preferably 2 to 6, specifically 1, 2, 3, 4, 5, 6, and

[0414] R x + R 7 Total number of carbon atoms (∑ carbon atoms R x , R 7 ) is 19 to 300, preferably 25 to 300, more preferably 35 to 300, even more preferably 50 to 300, specifically 35 to 200, more specifically 35 to 150, and even more specifically 50 to 150, and

[0415] R 11 It is preferably hydrogen, n-, iso-, or tert.-C1-C 22 Selected from the group consisting of -alkyl, more preferably hydrogen, and

[0416] R x is arbitrarily OH, -OC(O)-R 7 , -OC(O)-R 6 -(OC(O)-R 6 ) 0-19 -OC(O)-R 7 It is a substituted straight-chain, cyclic or branched, saturated or unsaturated hydrocarbon radical having 1 to 36 carbon atoms, preferably 1 to 24 carbon atoms, more preferably 1 to 18 carbon atoms, even more preferably 8 to 18 carbon atoms, preferably derived from a monohydroxycarboxylic acid, particularly glycolic acid, lactic acid, 2-hydroxybutyric acid, 3-hydroxy-butyric acid, 4-hydroxybutyric acid, 14-hydroxytetradecanoic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, resquerolic acid, or ricinoleic acid, or derived from a dihydroxycarboxylic acid, particularly 2,2'-di-hydroxymethylpropanoic acid, or 9,10-dihydroxystearic acid, or particularly gluconic acid Derived from polyhydroxycarboxylic acids,

[0417] R 6 is as defined above, and

[0418] R 7is an optionally substituted straight-chain, cyclic or branched, saturated or unsaturated hydrocarbon radical having 1 to 36 carbon atoms, preferably 1 to 24 carbon atoms, more preferably 1 to 18 carbon atoms, even more preferably 8 to 18 carbon atoms, and preferably derived from acetic acid, octanoic acid, nonanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanic acid, eicosanic acid, docosanic acid, 2-ethylhexanoic acid, 2,2-dimethylpropionic acid, 2,2-dimethylheptanoic acid, 2,2-dimethyloctanoic acid, neodecanoic acid, undecyl-10-en-acid, oleic acid, linoleic acid, linolenic acid, and erucic acid.

[0419] According to this specific example, R 6 This is independently selected from optionally hydroxyl-substituted hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, doicosylene, tricosylene and tetraicosylene, or hexenylene, heptenylene, octenylene, nonenylene, decenylene, undecenylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, doicosylene, tricosylene and tetraicosylene, and more preferably optionally Selected from hydroxyl-substituted hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, hexadecenylene, heptadecylene, octadecylene, nonadecylene, and eicocylene, most preferably each R 6 It is derived independently from ricinoleic acid, 10-hydroxy stearic acid, 12-hydroxy stearic acid, or resquerolic acid.

[0420] In a further preferred embodiment of the present invention, the formula R as defined above 1 (-F) x Compound of (I) is provided,

[0421] Here, R 1 It is selected from the group consisting of the following:

[0422] - Derived from a tertiary amine having at least three, preferably more than three, carbon atoms, which is monovalent to 18-valent, preferably divalent to 18-valent, more preferably divalent to 6-valent, even more preferably divalent, trivalent, and tetravalent, and is optionally a straight-chain, cyclic or branched, saturated, unsaturated, or aromatic hydrocarbyl group substituted with OH or amido, and is derived from a tertiary amine having at least three, preferably more than three, carbon atoms, in particular the tertiary amine is 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-dipropylentriaamine, 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, derived from condensates of epoxy compounds and alcohols, particularly glycidyl ethers, and in particular the alcohols are methanol, ethanol, 2-propanol, 1-butanol, t-butanol, undec-10-en-ol, oleyl alcohol, stearyl alcohol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,2-hexanediol, 1,6-hexanediol, glycerol, diglycerol, triglycerol and higher linear or branched oligoglycerols, trimethylolpropane, castor oil (ricinoleic acid triglycerides), pentaerythritol, sorbitol, poly(alkylene oxides) such as (ethylene oxide)-, (propylene oxide)- and / or (butylene oxide)-based polyethers, derived from polyethylene glycols such as diethylene glycol, triethylene glycol, tetraethylene glycol and pentaethylene glycol, etc., or dipropylene glycol (e.g., 2,Derived from 2'-oxydi-1-propanol, 1,1'-oxydi-2-propanol and 2-(2-hydroxypropoxy)-1-propanol), derived from polypropylene glycols such as tripropylene glycol, tetrapropylene glycol, and pentapropylene glycol, derived from mixed (ethylene oxide) and (butylene oxide)-based copolyethers, derived from mixed (propylene oxide) and (butylene oxide)-based copolyethers, derived from mixed (ethylene oxide)- and (propylene oxide)- and (butylene oxide)-based copolyethers, or preferred glycidyl esters, in particular neodecanoic acid, primary or secondary amino-functionalized amines, in particular N,N-dimethylpropylenediamine, N,N,N',N'-tetramethyl-diethylenetriamine, N,N,N',N'-tetramethyl-dipropylenediamine, N-methylmorpholine, N-methylpiperazine, and

[0423] - 1 to 18 valent, preferably 2 to 18 valent, more preferably 2 to 6 valent, even more preferably 2, 3, and 4 valent, and optionally a straight-chain, cyclic or branched, saturated, unsaturated, or aromatic hydrocarbon group substituted with OH, amino, or amido, and is derived from an alkyl halide having more than one, preferably more than two, carbon atoms, wherein the alkyl halide is an alkyl chloride, bromide, or iodide, e.g., 1,3-dichloropropane, 1,3-dichlorobutane, 1,4-dichlorobutane, dichloro-monohydroxypropane isomer, 1,2,3-trichloropropane, 1,2-dichlorohexanediol, 1,2-dichlorohexane, or their respective bromide and iodide derivatives, and

[0424] - derived from esters and alcohols of halogenated carboxylic acids, which are 1 to 18 valent, preferably 2 to 18 valent, more preferably 2 to 6 valent, even more preferably 2, 3, and 4 valent, and optionally OH, amino, or amido substituted straight-chain, cyclic or branched, saturated, unsaturated, or aromatic hydrocarbon groups, preferably chlorocarboxylic acids, and there are more than 2 total (esters), preferably more than 3, such as esters of chloroacetic acid, 3-chloropropionic acid, 4-chlorobutanoic acid, or each bromocarboxylic acid, and the alcohols are methanol, ethanol, 2-propanol, 1-butanol, t-butanol, undec-10-en-ol, oleyl alcohol, stearyl alcohol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,2-hexanediol, 1,6-hexanediol, glycerol, diglycerol, triglycerol and higher linear or branched oligoglycerols, trimethylolpropane, castor oil (ricinoleic acid triglycerides), pentaerythritol, sorbitol, poly(alkylene oxides) such as (ethylene oxide)-, (propylene oxide)- and / or (butylene oxide)-based polyethers, and derived from polyethylene glycols such as diethylene glycol, triethylene glycol, tetraethylene glycol and pentaethylene glycol, for example, dipropylene glycol (derived from, for example, 2,2'-oxydi-1-propanol, 1,1'-oxydi-2-propanol and 2-(2-hydroxypropoxy)-1-propanol), tripropylene glycol, tetrapropylene glycol, pentapropylene glycol, etc. Derived from polypropylene glycol, derived from a mixture of (ethylene oxide) and (butylene oxide)-based copolyethers, derived from a mixture of (propylene oxide)- and (butylene oxide)-based copolyethers, derived from a mixture of (ethylene oxide)- and (propylene oxide)- and (butylene oxide)-based copolyethers,

[0425] - Derived from an ether or ester and an alcohol of an epoxy compound having a total of more than 3, preferably more than 4, carbon atoms, and is a linear, cyclic or branched, saturated, unsaturated, or aromatic hydrocarbon group optionally substituted with OH, which is monovalent to 18-valent, preferably divalent to 18-valent, more preferably divalent to 6-valent, and even more preferably divalent, trivalent, and tetravalent, and is in particular the ether or ester of the epoxy compound is a glycidyl ether, and in particular the alcohol is methanol, ethanol, 2-propanol, 1-butanol, t-butanol, undec-10-en-ol, oleyl alcohol, stearyl alcohol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,2-hexanediol, 1,6-hexanediol, glycerol, Poly(alkylene oxides) such as diglycerol, triglycerol, higher linear or branched oligoglycerol, trimethylolpropane, castor oil (ricinoleic acid triglyceride), pentaerythritol, sorbitol, (ethylene oxide)-, (propylene oxide)-, and / or (butylene oxide)-based polyethers, derived from polyethylene glycols such as diethylene glycol, triethylene glycol, tetraethylene glycol, and pentaethylene glycol, for example; 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), tripropylene glycol, tetrapropylene glycol, and pentapropylene glycol; derived from mixed (ethylene oxide)- and (butylene oxide)-based copolyethers; and mixed Derived from (propylene oxide)- and (butylene oxide)-based copolyethers, derived from a mixture of (ethylene oxide)- and (propylene oxide)- and (butylene oxide)-based copolyethers, or preferably an acid which is a glycidyl ester and in particular a neodecanoic acid,

[0426] - A linear, cyclic or branched, saturated, unsaturated, or aromatic hydrocarbon group having 1 to 18 valent, preferably 2 to 18 valent, more preferably 2 to 6 valent, even more preferably 2, 3, and 4 valent optionally substituted with OH, amino, or amido, having a total of more than 2, preferably more than 3, carbon atoms, derived from esters and alcohols of halogenated carboxylic acids, preferably chlorocarboxylic acids, wherein the halogenated carboxylic acid is chloroacetic acid, 3-chloropropionic acid, 4-chlorobutanoic acid, or the respective bromocarboxylic acid, and together with an ether or ester of an epoxy compound, preferably a glycidyl ether, in particular the alcohol is methanol, ethanol, 2-propanol, 1-butanol, t-butanol, undec-10-en-ol, oleyl alcohol, stearyl alcohol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,2-hexanediol, 1,6-hexanediol, glycerol, diglycerol, triglycerol and higher linear or branched oligoglycerols, trimethylolpropane, castor oil (ricinoleic acid d-triglycerides), pentaerythritol, sorbitol, poly(alkylene oxide), e.g., poly(alkylene oxide)-, (propylene oxide)- and / or (butylene oxide)-based polyethers, and is particularly derived from polyethylene glycols such as diethylene glycol, triethylene glycol, tetraethylene glycol and pentaethylene glycol, or dipropylene glycol (particularly, 2,2'-oxydi-1-propanol, 1,1'-oxydi-2-propanol and 2- Derived from (2-hydroxypropoxy)-1-propanol), derived from polypropylene glycols such as tripropylene glycol, tetrapropylene glycol, and pentapropylene glycol, derived from mixed (ethylene oxide)- and (butylene oxide)-copolyethers, derived from mixed (propylene oxide)- and (butylene oxide)-copolyethers,Derived from a mixture of (ethylene oxide)- and (propylene oxide)- and (butylene oxide)-based copolyethers, or preferably an acid which is a glycidyl ester and in particular a neodecanoic acid,

[0427] - A linear, cyclic or branched, saturated, unsaturated, or aromatic hydrocarbon group optionally OH-substituted, having 1 to 18 valent, preferably 2 to 18 valent, more preferably 2 to 6 valent, even more preferably 2, 3, and 4 valent, having a total of more than 7, preferably more than 8, carbon atoms, formed from an ether of an epoxy compound, particularly a glycidyl ether, and a carboxylic acid of 2 to 6 valent, in particular the carboxylic acid is maleic acid, succinic acid, adipic acid, sebacic acid, itaconic acid, tartaric acid, trimellitic acid, fatty acid dimer, carboxyl (-C(O)OH) functionalized polyester, particularly preferably formed by the condensation of a carboxylic acid of 2 to 6 valent and the above-mentioned 2 to 6 valent alcohol or alkylene oxide, for example the carboxylic acid is maleic acid, succinic acid, adipic acid, Sebacic acid, itaconic acid, tartaric acid, trimellitic acid, and fatty acid dimers are alkylene oxides, ethylene oxide, propylene oxide, butylene oxide and compounds containing at least one glycidoxy group such as glycidol, diglycidyl ether, glycerol diglycidyl ether, glycerol triglycidyl ether and glycerol glycidyl ether oligomers, butanediol diglycidyl ether, in particular succinic acid, maleic acid and tartaric acid, fatty acid dimers and glycerol glycidyl ether, and polyester condensation products are derived from oligomerized hydroxycarboxylic acids, particularly preferably oligomerized lactic acid, 12-hydroxy stearic acid, resquerolic acid, and ricinoleic acid, and

[0428] - A linear, cyclic or branched, saturated, unsaturated, or aromatic hydrocarbon group optionally OH-substituted, of 1 to 18 valent, preferably 2 to 18 valent, more preferably 2 to 6 valent, and even more preferably 2, 3, and 4 valent, and

[0429] Derived from esters of halogenated carboxylic acids having a total of more than 5, preferably more than 6, carbon atoms, preferably chlorocarboxylic acids, and OH-functionalized polyesters, wherein the halogenated carboxylic acids are chloroacetic acid, 3-chloropropionic acid, 4-chlorobutanoic acid, or their respective bromocarboxylic acids, and particularly preferably formed by the condensation of divalent to hexavalent carboxylic acids, for example, the carboxylic acids are maleic acid, succinic acid, adipic acid, sebacic acid, itaconic acid, tartaric acid, trimellitic acid, fatty acid dimers, divalent to hexavalent alcohols as mentioned above, or alkylene oxides, and the alkylene oxides are ethylene oxide, propylene oxide, butylene oxide, and glycidol, diglycidyl ether, glycerol diglycidyl ether, glycerol triglycidyl ether, and glycerol glycidyl ether. It is a compound containing one or more glycidoxy groups, such as oligomers, butanediol diglycidyl ethers, and in particular, a condensation product of succinic acid, maleic acid, and tartaric acid or fatty acid dimers and glycerol diglycidyl ethers.

[0430] In a further preferred embodiment of the present invention, the formula R as defined above 1 (-F) x Compound of (I) is provided,

[0431] Here, R 1 is selected from poly(alkylene oxide) groups, preferably selected from poly(alkylene oxide) groups of formula (IX), and

[0432] -[CH2CH2O] q1 -[CH2CH(CH3)O] r1 -[CH2CH(C2H5)O] s1-{[CH2CH2] q2 -[CH2CH(CH3)] r2 -[CH2CH(C2H5)] s2}- (IX)

[0433] q1 = 0 to 49, preferably 0 to 10, more preferably 1 to 10, even more preferably 1 to 5, and

[0434] r1 = 0 to 32, preferably 0 to 10, more preferably 1 to 10, even more preferably 1 to 5, and

[0435] s1 = 0 to 24, preferably 0 to 10, more preferably 1 to 10, even more preferably 1 to 5, and

[0436] q2=0 or 1, and

[0437] r2=0 or 1, and

[0438] s2=0 or 1 and,

[0439] ∑(q2+r2+s2)=1 and,

[0440] However, the sum of carbon atoms of such poly(alkylene oxide) groups is 2 to 100, preferably 2 to 50, more preferably 2 to 30, even more preferably 2 to 20, specifically 2 to 15, or

[0441] R 1 is selected from a divalent hydrocarbon group derived from an oligoglycerol of chemical formula (X), and

[0442] -[CH2CH(R 8 )CH2O] t1 -[CH2CH(R 8 )CH2)] t2 - (X)

[0443] t1 = 0 to 32, preferably 0 to 10, more preferably 1 to 10, even more preferably 1 to 5, specifically 1 and 2, and

[0444] t2=1 and,

[0445] 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 ) and,

[0446] Here, m, X, R 3 , R 4 , R 5 , R 6 and R 7 is as defined above, and

[0447] However, the sum of carbon atoms is 2 to 100, preferably 2 to 50, more preferably 2 to 30, even more preferably 2 to 20, specifically 2 to 15, or R 1 is selected from divalent hydrocarbon groups comprising at least one ester group of formula (XI) and formula (XII), and

[0448] -[CH2CH2O] q1 -R 9 -[CH2CH2O] q1 -[CH2CH2] q2 - (XI)

[0449] q1 is the same or different, as defined above, q2=1, and

[0450] -[CH2CH(R 8 )CH2O] t1 -R 9 -[CH2CH(R 8 )CH2O] t1 -[CH2CH(R 8 )CH2)] t2 - (XII)

[0451] t1, t2 and R 8 is as defined above, and

[0452] R 9 -C(O)C(O)O-, -C(O)(CH2) 1-8 Selected from C(O)O-, e.g. derived from succinic acid, adipic acid, sebacic 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-, and

[0453] However, R 9 The sum of the carbon atoms is 2 to 100, preferably 2 to 50, more preferably 2 to 30, even more preferably 2 to 20, specifically 2 to 15.

[0454] According to this embodiment, preferably q2 = 0, and one or two of q1, r1 and s1 are 0, and more preferably

[0455] q2 = 0 and r1 and s1 are 0, or

[0456] q2 = 0, and q1 and s1 are 0.

[0457] In a further preferred embodiment of the present invention, the compound of formula (I) is as defined in the above embodiment, and R 1 It contains one or more -O- groups such as 1 to 5. These -O- groups are preferably ether groups, but may also form ester groups with carbonyl groups, and preferably R 1 The group is replaced with one or more hydroxyl groups.

[0458] In a further preferred embodiment of the present invention, as defined above, formula R 1 (-F) x Compound of (I) is provided,

[0459] Here

[0460] Radical R 1 , R 3 , R 4 , R5 One or more of N + In the case of being combined with

[0461] It contains at least one moiety of chemical formula (III) or (IV), and

[0462] (-XC(O)-R 6 ) m -XC(O)- (III) or

[0463] (-C(O)-XR 6 ) m -C(O)-X- (IV),

[0464] Preferably containing at least one moiety of formula (IIIa) or (IVa),

[0465] (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa), 또는

[0466] (-C(O)-XR 6 ) m -C(O)-XR 7 (IVa)

[0467] m = 1 to 20, and X, R 6 and R 7 is as defined above, and

[0468] At least one moiety has the structure of chemical formula (XIII) or (XIV),

[0469] -R 10 (-XC(O)-R 6 ) m -XC(O)- (XIII) or

[0470] -R 10 (-C(O)-XR 6 ) m -C(O)-X- (XIV),

[0471] Preferably, the formulas are (XIIIa) and (XIVa), and

[0472] -R 10 (-XC(O)-R 6 )m -XC(O)-R 7 (XIIIa)

[0473] -R 10 (-C(O)-XR 6 ) m -C(O)-XR 7 (XIVa)

[0474] Here, R 10 It is an optionally substituted hydrocarbon radical having 2 to 18 valence, preferably 2 to 10 valence, more preferably 2 to 10 valence, specifically 2, 3, 4, 5, 6, 7, 8, 9, and 10 valence, and has up to 200 carbon atoms, preferably 2 to 200 carbon atoms, more preferably 2 to 100 carbon atoms, even more preferably 2 to 50 carbon atoms, specifically 2 to 20 carbon atoms, more specifically 2 to 10 carbon atoms, and has -O-, -NH-, -C(O)-, -C(S)-, tertiary amino group ( ), quaternary ammonium group ( It may optionally contain one or more groups selected from ), and may be substituted with -OH or a halide group, where radical R 10 It may not contain a combination of -C(O)- and -O- groups forming an internal carboxylate group or an internal amide group, or a combination of -C(O)- and -NH- or tertiary amino groups, and

[0475] Preferably R 10 It is displayed as follows.

[0476] - A divalent radical, particularly -CH2-, -CH2CH2-, -CH2CH2CH2-, preferably derived from a monochlorocarboxylic acid such as chloroacetic acid, chloropropionic acid, or chlorobutanoic acid, or preferably derived from a tertiary amino alcohol such as N,N-dimethylethanolamine or N,N-dimethylpropanolamine, and

[0477] - A trivalent radical, preferably derived from a partial ester of the aforementioned monochlorocarboxylic acid and a tertiary alcohol, in particular the monochlorocarboxylic acid is chloroacetic acid, in particular the tertiary alcohol is glycerol, trimethylolpropane, or castor oil (ricinoleic acid triglyceride), or preferably derived from a tertiary amino alcohol which is N,N,N'-trimethylaminoethyl-ethanolamine, or preferably derived from an ester of a tertiary amino alcohol which is N,N-dimethylethanolamine or N,N-dimethylpropanolamine, and in particular from a dihydroxycarboxylic acid which is 2,2-hydroxymethylpropanoic acid,

[0478] - Derived from a tetravalent to hexavalent radical, preferably derived from a partial ester of the aforementioned monochlorocarboxylic acid and a quaternary alcohol, a pentavalent alcohol, and a hexavalent alcohol, in particular the monochlorocarboxylic acid is chloroacetic acid, in particular the quaternary alcohol is erythritol, pentaerythritol, or diglycerol, in particular the pentavalent alcohol is xylitol or triglycerol, in particular the hexavalent alcohol is sorbitol or tetraglycerol, or preferably derived from an ester of a tertiary amino alcohol, particularly N,N-dimethylethanolamine or N,N-dimethylpropanolamine, and in particular the dendrimer oligomer of a dihydroxycarboxylic acid oligomer, which is a dendrimer oligomer of 2,2-hydroxymethylpropanoic acid, and

[0479] Heptary to octavalent radicals, preferably derived from a partial ester of the aforementioned monochlorocarboxylic acid and a heptary to octavalent alcohol, in particular the monochlorocarboxylic acid is chloroacetic acid, and in particular the heptary to octavalent alcohol is pentaglycerol to hexadecaglycerol,

[0480] However, R 10 N by single bond + Connected to a moiety and connected to at least one radical, preferably 1, 2, 3, and 4 radicals of the structure of formula (III) or (IV), and

[0481] (-XC(O)-R 6) m -XC(O)- (III) or

[0482] (-C(O)-XR 6 ) m -C(O)-X- (IV),

[0483] More preferably connected to the 1st, 2nd, 3rd, and 4th radicals of formula (IIIa) or (IVa), and

[0484] (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa)

[0485] (-C(O)-XR 6 ) m -C(O)-XR 7 (IVa)

[0486] X, m, R 11 , R 6 , R 7 is as defined above.

[0487] According to the above specific example, preferably

[0488] X=O and,

[0489] R 6 is optionally independently selected from hydroxyl-substituted hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, doicosylene, tricosylene, and tetracoene, or hexenylene, heptenylene, octenylene, nonenylene, decenylene, undecenylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, doicosylene, tricosylene, and tetraicosylene, most preferably wherein the groups are Bonded to an adjacent C(O) group or O group by a terminal C-atom, and

[0490] If present, R 7is optionally independently selected from hydroxyl-substituted hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, henicosyl, doicosyl, tricosyl and tetracocene, or hexenyl, heptenyl, octenyl, nonenyl, desenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicocenyl, henicosyl, doicocenyl, tricocenyl and tetraicocenyl, most preferably wherein these groups are bonded to an adjacent C(O) group by a terminal C-atom, and

[0491] m is 1 to 10, preferably 1, 2, 3, 4 or 5.

[0492] More preferably, X = O and,

[0493] R 6 is selected from hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, hexadecenylene, heptadecylene, octadecylene, nonadecylene, and eicosylene, and

[0494] If present, R 7 is selected from hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl hexadecenyl, heptadecyl, octadecyl, nonadecyl, and eicosyl, and

[0495] m is 1, 2, 3, 4, or 5.

[0496] In these embodiments, most preferably

[0497] X = O and,

[0498] R 6 It is derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or resquerolic acid, and

[0499] If present, R 7 It is derived from oleic acid, ricinoleic acid, or stearic acid, and

[0500] m is 1, 2, 3, 4, or 5.

[0501] In a further preferred embodiment of the present invention, as defined in the previous embodiment, formula R 1 (-F) x Compound of (I) is provided,

[0502] Here, regarding moiety

[0503] -R 10 (-XC(O)-R 6 ) m -XC(O)- (XIII) or

[0504] Preferably R 10 (-XC(O)-R 6 ) m -XC(O)-R 7 (XIIIa) and,

[0505] R 10 X adjacent to is O, and

[0506] R 10 It is derived from mono- or di-(chloroacetic acid) esters of glycerol or castor oil (ricinoleic acid triglycerides), and consists of one or two moieties in total (-XC(O)-R 6 ) m -XC(O)-, preferably (-XC(O)-R 6 ) m -OC(O)-R 7 Combine with,

[0507] - or R 10 It is derived from esters of tertiary amino alcohols, in particular the amino alcohols are N,N-dimethylethanolamine, N,N-dimethylpropanolamine, and N,N,N'-trimethylaminoethylethanolamine, and overall one moiety (-XC(O)-R 6 ) m -OC(O)-R 7 , preferably (-XC(O)-R 6 ) m -OC(O)-R 7 Combine with,,

[0508] or R 10 It is derived from esters of tertiary amino alcohols and dihydroxycarboxylic acids, in particular the amino alcohols are N,N-dimethylethanolamine and N,N-dimethylpropanolamine, in particular the dihydroxycarboxylic acid is 2,2-hydroxymethylpropanoic acid, and overall two moieties (-XC(O)-R 6 ) m -XC(O)-, preferably (-XC(O)-R 6 ) m -OC(O)-R 7 Combine with,

[0509] or R 10 It is derived from esters of tertiary amino alcohols and, in particular, dendritic oligomers of dihydroxycarboxylic acids, which are dendrimer oligomers of 2,2-hydroxymethylpropanoic acid, in particular the amino alcohols are N,N-dimethylethanolamine and N,N-dimethylpropanolamine, and, in total, more than two, preferably three or four moieties (-XC(O)-R 6 ) m -XC(O)-, preferably (-XC(O)-R 6 ) m -OC(O)-R 7 Combine with,

[0510] About Moiety

[0511] - R 10 (-XC(O)-R 6 ) m -XC(O)- (XIII) or preferably

[0512] - R 10 (-XC(O)-R 6 ) m -XC(O)-R 7 (XIIIa) and,

[0513] R 10 X adjacent to is N, and

[0514] R 10It is derived from tertiary-primary amines, particularly N,N-dimethyl-1,3-propanediamine and N-methyl-N'-aminopropyl-piperazine, and tertiary-secondary amines, particularly N-methylpiperazine, and

[0515] Regarding both types of moiety,

[0516] R 6 is as defined above, preferably derived from lactic acid, ricinoleic acid, resquerolic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, 14-hydroxytetradecanoic acid, most preferably derived from ricinoleic acid or resquerolic acid, and

[0517] R 7 is as defined above, and preferably derived from octadecanic acid, eicosanic acid, docosanic acid, 2-ethylhexanoic acid, 2,2-dimethylpropionic acid, neodecanoic acid, and oleic acid,

[0518] m = 1 to 20, preferably 1 to 10, more preferably 1 to 6, even more preferably 2 to 6, specifically 1, 2, 3, 4, 5, 6, 7, and

[0519] R 6 + R 7 The total number of carbon atoms (∑ R 6 and R 7 The carbon atoms) are 19 to 300, preferably 25 to 300, more preferably 35 to 300, even more preferably 50 to 300, specifically 35 to 200, more specifically 35 to 150, and even more specifically 50 to 150, and

[0520] R 11 It is preferably selected from the group consisting of hydrogen or, in particular, ring-forming alkylenes derived from a piperazine ring.

[0521] In a further preferred embodiment of the present invention, the formula R defined in the previous two embodiments 1 (-F)x Compound of (I) is provided,

[0522] Here

[0523] R 6 is as defined above, preferably derived from lactic acid, ricinoleic acid, resquerolic acid, 10-hydroxy stearic acid, 12-hydroxy stearic acid, 14-hydroxy tetradecanoic acid, most preferably derived from ricinoleic acid or resquerolic acid, and

[0524] R 7 is as defined above, and preferably derived from octadecanic acid, eicosanic acid, docosanic acid, 2-ethylhexanoic acid, 2,2-dimethylpropionic acid, neodecanoic acid, and oleic acid,

[0525] About Moiety

[0526] - R 10 (-XC(O)-R 6 ) m -XC(O)- (XIII) and

[0527] - R 10 (-C(O)-XR 6 ) m -C(O)-X- (XIV) and,

[0528] Preferably regarding moiety,

[0529] - R 10 (-XC(O)-R 6 ) m -XC(O)-R 7 (XIIIa) and

[0530] - R 10 (-C(O)-XR 6 ) m -C(O)-XR 7 (XIVa) and

[0531] If R7 is present within the ester segment, radical R 6 The sequence is either random or block-like, and with respect to the block-like sequence, the compound contains the structure of formula (XV) or (XVI), and

[0532] - R 10 -XC(O)-R 6 (-XC(O)-R 61 ) m1 (-XC(O)-R 62 ) m2 -XC(O)- (XV)

[0533] - R 10 -C(O)-XR 6 (-C(O)-XR 61 ) m1 (-C(O)-XR 62 ) m2 -C(O)-X- (XVI),

[0534] Preferably containing the structure of the chemical formula (XVa) or (XVIa),

[0535] - R 10 -XC(O)-R 6 (-XC(O)-R 61 ) m1 (-XC(O)-R 62 ) m2 -XC(O)-R 7 (XVa)

[0536] - R 10 -C(O)-XR 6 (-C(O)-XR 61 ) m1 (-C(O)-XR 62 ) m2 -C(O)-XR 7 (XVIa)

[0537] R 61 and R 62 is R 6 Selected from,

[0538] m1 = 0 to 20, preferably 0 to 10, more preferably 0 to 6, even more preferably 1 to 6, specifically 0, 1, 2, 3, 4, 5, 6, and

[0539] m2 = 0 to 20, preferably 0 to 10, more preferably 0 to 6, even more preferably 1 to 6, specifically 0, 1, 2, 3, 4, 5, 6, and

[0540] m = (m1+m2)+1 and,

[0541] m = 1 to 20, preferably 1 to 10, more preferably 1 to 6, even more preferably 1 to 6, specifically 1, 2, 3, 4, 5, 6, 7, and

[0542] R 6 + R 7 The total number of carbon atoms (∑ R 6 and R 7 The carbon atoms) are 19 to 300, preferably 25 to 300, more preferably 35 to 300, even more preferably 50 to 300, specifically 35 to 200, more specifically 35 to 150, and even more specifically 50 to 150.

[0543] Here, the sequences of chemical formulas (XV) and (XVI) are preferably selected from below, and

[0544]

[0545] The sequence of the structures of chemical formulas (XVa) and (XVIa) is preferably selected from below.

[0546]

[0547] According to this specific example, R 6 , R 61 , R 62 A combination of or R 6 , R 61 , R 62 and R 7 It is particularly desirable that the combination is selected according to a specific compound named in one of the lines of the table above.

[0548] R, which is monomodal or polymodal in relation to molecular weight distribution 6 Incorporating the containing ester segment into the lower moiety is generally within the scope of the present invention.

[0549] (-XC(O)-R 6 ) m -XC(O)- (III) and

[0550] (-C(O)-XR 6 ) m -C(O)-X- (IV)

[0551] In the context of the present invention, the term monomodal means that 80% or more of the ester segments have the same molecular weight. The term polymodal means that individual ester segments do not reach 80% of the total composition.

[0552] R, which is monomodal or polymodal in relation to molecular weight distribution 6 and R 7 Incorporating the containing ester segment into the lower moiety is also generally within the scope of the present invention.

[0553] (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa) and

[0554] (-C(O)-XR 6 ) m -C(O)-XR 7 (IVa)

[0555] In particular, R which is monomodal or polymodal in relation to molecular weight distribution 6 and if present R 7 Incorporating the containing ester segment into the lower moiety is within the scope of the present invention.

[0556] -R 10 (-XC(O)-R 6 ) m -XC(O)- (XIII) and

[0557] -R 10 (-C(O)-XR 6 ) m -C(O)-X- (XIV),

[0558] In particular, it is the moiety below, and

[0559] -R 10 (-XC(O)-R 6 ) m -XC(O)-R 7 (XIIIa) and

[0560] -R 10 (-C(O)-XR 6 ) m -C(O)-XR 7 (XIVa)

[0561] The terms "monomodal" and "polymodal" have the meanings defined above.

[0562] According to the present embodiment, preferably

[0563] X=O and,

[0564] R 6 is optionally independently selected from hydroxyl-substituted hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, doicosylene, tricosylene, and tetraicosylene, or hexenylene, heptenylene, octenylene, nonenylene, decenylene, undecenylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, doicosylene, tricosylene, and tetraicosylene, wherein the Most preferably, it is bonded to an adjacent C(O) group or O group by a terminal-C atom, and

[0565] In cases where it exists, R 7is optionally independently selected from hydroxyl-substituted hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, henicosyl, doicosyl, tricosyl and tetraicosyl, or hexenyl, heptenyl, octenyl, nonenyl, desenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosyl, henicosyl, doicosyl, tricosyl and tetraicosyl, wherein the group is most preferably bonded to an adjacent C(O) group by a terminal C-atom, and

[0566] m is 1 to 10, preferably 1, 2, 3, 4 or 5.

[0567] More preferably, X = O and,

[0568] R 6 is selected from hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, hexadecenylene, heptadecylene, octadecylene, nonadecylene, and eicosylene, and

[0569] In cases where it exists, R 7 is selected from hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl hexadecenyl, heptadecyl, octadecyl, nonadecyl, and eicosyl, and

[0570] m is 1, 2, 3, 4, or 5.

[0571] Most preferably in these embodiments,

[0572] X = O and,

[0573] R 6 It is derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or resquerolic acid, and

[0574] In cases where it exists, R 7 It is derived from oleic acid, ricinoleic acid, or stearic acid, and

[0575] m is 1, 2, 3, 4, or 5.

[0576] Incorporating one or more types of the following moieties (mixtures of different structures) into a compound according to the present invention, which may be a mono-, di-, and polyquaternary compound, is also within the scope of the present invention.

[0577] (-XC(O)-R 6 ) m -XC(O)- (III) and

[0578] (-C(O)-XR 6 ) m -C(O)-X- (IV)

[0579] Accordingly, incorporating one type or more than one type of the following moiety (a mixture of different structures) into a compound according to the present invention is also within the scope of the present invention, and

[0580] (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa) and

[0581] (-C(O)-XR 6 ) m -C(O)-XR 7 (IVa),

[0582] In addition, incorporating one or more types of the following moiety (mixtures of different structures) into the compound according to the present invention is also within the scope of the present invention, and

[0583] -R 10 (-XC(O)-R 6 ) m -XC(O)- (XIII) and

[0584] -R 10 (-C(O)-XR 6 ) m -C(O)-X- (XIV)

[0585] In particular, incorporating one or more types of the following moiety (mixtures of different structures) into the compound according to the present invention is also within the scope of the present invention.

[0586] -R 10 (-XC(O)-R 6 ) m -XC(O)-R 7 (XIIIa) and

[0587] -R 10 (-C(O)-XR 6 ) m -C(O)-XR 7 (XIVa).

[0588] According to the present invention, R within the moiety below 6 Contains ester components,

[0589] (-XC(O)-R 6 ) m -XC(O)- (III),

[0590] (-C(O)-XR 6 ) m -C(O)-X- (IV),

[0591] In particular, R within the moiety below 6 and R 7 Contains ester components,

[0592] (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa) and

[0593] (-C(O)-XR 6 ) m -C(O)-XR 7 (IVa),

[0594] More specifically, R within the moiety below 6 and R 7 Contains ester components,

[0595] - R 10 (-XC(O)-R 6 ) m -XC(O)- (XIII),

[0596] - R 10 (-C(O)-XR 6 ) m -C(O)-X- (XIV)

[0597] - R 10 (-XC(O)-R 6 ) m -XC(O)-R 7 (XIIIa) and

[0598] - R 10 (-C(O)-XR 6 ) m -C(O)-XR 7 (XIVa),

[0599] For example, R within the moiety below 6 and R 7 The contained ester components are,

[0600] - R 10 -OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-,

[0601] - R 10 -NR 1 -C(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-,

[0602] - R 10 -OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7 and

[0603] - R 10 -NR 1 -C(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7 ,

[0604] It can be synthesized from the corresponding carboxylic acid by esterification using a method known in the prior art. In a preferred embodiment, such esterification can be performed thermally under reduced pressure at 150 to 350°C, preferably 180 to 250°C (US2011 / 0282084, GB 841554, DE 694943).

[0605] In addition, esterification can be performed using a catalyst (EP 3009494, WO 2012069386, DD 150064, CH 151317, TA Isbell, Grasas y Aceites, 2011, 62(1), 8-20). In another preferred embodiment, carboxylic acids can be condensed using an enzyme (JP 05304966, JP 05211878, JP 01016591, A. Bodalo et al., Biochem. Eng. J., 2008, 39(3), A.450-456, 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). In general, the method described above provides a polymodal condensate.

[0606] Generally, monomodal condensates can be synthesized by a condensation sequence based on the step esterification of a carboxylic acid anhydride (K. Meier, Farbe und Lack, 1951, 57, 437-439; FHH Valentin, J. South African Chem. Inst. 1949, 2, 59-61), or preferably a carboxylic acid chloride and the OH group of a hydroxylated carboxylic acid and its derivative (KD Pathak et al., J. Scientific & Industrial Research, 1955, 14B, 637-639).

[0607] The repetition of a cycle based on esterification and acid chloride synthesis generally yields monomodal ester condensates. Further details are explained in the Examples section.

[0608] Below, the synthesis sequence of ester condensates based on the stepwise esterification of OH groups of carboxylic acid chlorides, hydroxylated carboxylic acids, and their derivatives is schematically shown.

[0609]

[0610] Here, the arrow indicates the product obtained by the esterification reaction of the acyl chloride of the fatty acid R1-C(O)Cl and the hydroxyl-carboxylic acid HO-R2-C(O)OH, and the acyl chloride subsequently formed by the reaction with SOCl2 can be applied again to such a reaction sequence. Thus, in the next reaction sequence, R1 of the starting material R1-C(O)Cl is "R1-C(O)O-R2" of the previous reaction sequence. Thus, the estolide structure can be obtained in a repetitive manner, and the number of fatty acid residues included in the final estolide moiety is determined by the number of repetitive steps of the cyclic process.

[0611] Carboxylic acids without OH groups terminate the chains of ester condensates. Monohydroxycarboxylic acids extend the chains of ester condensates. Generally, dihydroxy and polyhydroxycarboxylic acids provide branched and dendrimer (self-repeating) elements within ester condensates.

[0612] In a further preferred embodiment of the present invention, the formula R as defined above 1 (-F) x Compound of (I) is provided,

[0613] Here, the low-melting point and high-melting point fatty acids with C5 or higher are specifically R of chemical formulas (III) and (IV). 6 Located within the contained ester element,

[0614] (-XC(O)-R6 ) m -XC(O)- (III)

[0615] (-C(O)-XR 6 ) m -C(O)-X- (IV),

[0616] In particular, R of chemical formulas (IIIa) and (IVa) 6 and R 7 Located within the contained ester element, or

[0617] (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa) and

[0618] (-C(O)-XR 6 ) m -C(O)-XR 7 (IVa)

[0619] Or, located within the R6-containing ester elements of chemical formulas (XIII) and (XIV),

[0620] -R 10 (-XC(O)-R 6 ) m -XC(O)- (XIII)

[0621] -R 10 (-C(O)-XR 6 ) m -C(O)-X- (XIV),

[0622] In particular, it is located within the ester elements containing R6 and R7 of chemical formulas (XIIIa) and (XIVa).

[0623] -R 10 (-XC(O)-R 6 ) m -XC(O)-R 7 (XIIIa)

[0624] -R 10 (-C(O)-XR 6 ) m -C(O)-XR 7 (XIVa).

[0625] Generally, C5 or higher low-melting point and high-melting point fatty acids are located specifically in the respective ester groups of moiety selected from the moiety of formulas (III), (IV), (IIIa), (IVa), (XIII), (XIV), (XIIIa), and (XIVa) present in the compound of formula (I). For example, as described below, if the number of moiety of formula (III) indicates a specific position of the low-melting point fatty acid and high-melting point fatty acid scaffold, it follows this embodiment of the invention, whereas other moiety of formula (III) does not. This is particularly true for different residue R as defined above. 1 , R 2 , R 3 , R 4 and R 5 It may be the case of a moiety existing in.

[0626] Within the framework of the present invention, C5 or higher low-melting point fatty acids are defined as having a melting point ≤ 40°C. Preferred examples are particularly oleic acid, resquerolic acid, ricinoleic acid, octanoic acid, decanoic acid, pivalic acid, and neodecanoic acid.

[0627] Within the framework of the present invention, high melting point fatty acids with C5 or higher are defined as having a melting point > 40°C. Preferred examples are particularly dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanic acid, arachidic acid, behenic acid, 10-hydroxyoctadecanic acid, 12-hydroxyoctadecanic acid, and 14-hydroxytetradecanoic acid.

[0628] The corresponding melting points can be taken from the literature (G. Knothe et al., J Am Oil Chem Soc, 2009, 86, 844-856).

[0629] In a further preferred embodiment according to the present invention, the formula R as defined above 1 (-F) x Compound of (I) is provided,

[0630] Here, at least one, preferably more than one, more preferably one, two or three C5 or more, each R 6 The low-melting point fatty acid forming the group is R of chemical formula (III) or (IV). 6 - Located at one end of the ester component containing, on the other hand, at least one, preferably more than one, more preferably one, two, or three C5 or higher high melting point fatty acids are located at the opposite end of formula (III) or (IV) a radical or radical R 6 Forming, or at least one, preferably more than one, more preferably one, two or three C5 or more, each R 6 Each of the high-melting point fatty acids forming the group is R of chemical formula (III) or (IV). 6 - Located at one end of the ester component containing, while at least one, preferably more than one, more preferably one, two, or three C5 or higher low-melting point fatty acids are located at the opposite end of formula (III) or (IV) a radical or radical R 6 It is a method of forming, or

[0631] - At least one, preferably more than one, more preferably one, two or three C5 or more, each R 6 The low-melting point fatty acid that forms the group is R 7 Radical or radical R adjacent to 6 Contained in, on the other hand, at least one, preferably more than one, more preferably one, two or three C5 or higher high melting point fatty acids are R of formula (IIIa) or (IVa). 6 and R 7 Radical or radical R at the opposite end of the contained ester component 6 Forming, or at least one, preferably more than one, more preferably one, two or three C5 or more, each R 6 The high-melting-point fatty acid that forms the group is R7 Radical or radical R adjacent to 6 Forming, on the other hand, at least one, preferably more than one, more preferably one, two or three C5 or higher low-melting point fatty acids are R of formula (IIIa) or (IVa). 6 and R 7 Radical or radical R at the opposite end of the contained ester component 6 It is a method of forming, or

[0632] - At least one, preferably more than one, more preferably one, two or three C5 or more, each R 6 The low-melting point fatty acid that forms the group is R 10 Located adjacent to, on the other hand, at least one, preferably more than one, more preferably one, two, or three C5 or higher high melting point fatty acids are radicals or radical R at the opposite end of the ester component of formula (XIII) or (XIV). 6 Forming, or at least one, preferably more than one, more preferably one, two or three C5 or more, each R 6 The high-melting-point fatty acid that forms the group is R 10 Radical or radical R adjacent to 6 Forming, on the other hand, at least one, preferably more than one, more preferably one, two or three C5 or higher low-melting point fatty acids are R of formula (XIII) or (XIV). 6 and R 7 Radical or radical R at the opposite end of the contained ester component 6 It is a method of forming, or

[0633] - At least one, preferably more than one, more preferably one, two or three C5 or more, each R 6 The low-melting point fatty acid that forms the group is R 10Located adjacent to, on the other hand, at least one, preferably more than one, more preferably one, two, or three C5 or higher high melting point fatty acids are located in the moiety of formula (XIIIa) or (XIVa) R 7 Radical or radical R adjacent to 6 Forming, or at least one, preferably more than one, more preferably one, two or three C5 or more, each R 6 The high-melting-point fatty acid that forms the group is R 10 Radical or radical R adjacent to 6 Forms, on the other hand, at least one, preferably more than one, more preferably one, two or three C5 or higher low-melting point fatty acids are R in the moiety of formula (XIIIa) or (XIVa). 7 Radical or radical R adjacent to 6 It is a method of forming.

[0634] As already mentioned above, the specific positions of high-melting and low-melting fatty acids are each individual R of the given chemical formula. 6 - It can vary independently of the contained ester moiety.

[0635] The preferred embodiment outlined above is R, which has a tendency to change locally with respect to crystallization, viscosity increase, and phase formation over the entire length of this ester component in the moiety of the formula below. 6 - Not only contains R 6 and R 7 It allows the incorporation of contained ester components.

[0636] (-XC(O)-R 6 ) m -XC(O)- (III)

[0637] (-C(O)-XR 6 ) m -C(O)-X- (IV),

[0638] (-XC(O)-R6 ) m -XC(O)-R 7 (IIIa) BC

[0639] (-C(O)-XR 6 ) m -C(O)-XR 7 (IVa),

[0640] -R 10 (-XC(O)-R 6 ) m -XC(O)-(XIII),

[0641] -R 10 (-C(O)-XR 6 ) m -C(O)-X-(XIV),

[0642] -R 10 (-XC(O)-R 6 ) m -XC(O)-R 7 (XIIIa) 및

[0643] -R 10 (-C(O)-XR 6 ) m -C(O)-XR 7 (XIVa),

[0644] 특히,

[0645] -R 10 -OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-,

[0646] -R 10 -NR 1 -C(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-,

[0647] -R 10 -OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7 및

[0648] -R 10 -NR 1-C(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7 .

[0649] The intentional combination of the aforementioned carboxylic acid and synthetic concepts provides access to ester condensates with defined characteristics such as molecular weight, molecular weight distribution, carboxylic acid sequence, and viscosity.

[0650] Generally, radical R 10 R in a different way from the chemical formula below 6 Contains and R 6 and R 7 It can be linked to the contained ester components.

[0651] -R 10 (-XC(O)-R 6 ) m -XC(O)-R 7 (XIII),

[0652] -R 10 (-C(O)-XR 6 ) m -C(O)-XR 7 (XIV),

[0653] -R 10 (-XC(O)-R 6 ) m -XC(O)-R 7 (XIIIa) and

[0654] -R 10 (-C(O)-XR 6 ) m -C(O)-XR 7 (XIVa),

[0655] especially,

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

[0657] -R 10 -NR1 -C(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-,

[0658] -R 10 -OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7 and

[0659] -R 10 -NR 1 -C(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7

[0660] In a preferred embodiment according to the present invention, a compound of formula (I) as defined in a previous embodiment is provided, and

[0661] Preferably R of the following chemical formula 10 2 or more moiety -OC(O)-R 6 -(OC(O)-R 6 ) m Derived from mono- or di-(chloroacetic acid) esters of glycerol or castor oil (ricinoleic acid triglycerides) containing -OC(O)-, or a total of one or two moiety -OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7 It is combined with.

[0662] -R 10 (-XC(O)-R 6 ) m -XC(O)- (XIII)

[0663] -R 10 (-XC(O)-R 6 ) m -XC(O)-R 7 (XIIIa), more preferably

[0664] -R 10 -OC(O)-R6 -(OC(O)-R 6 ) m -OC(O)-,

[0665] -R 10 -OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7

[0666] According to this embodiment, preferably

[0667] X=O and,

[0668] R 6 is optionally independently selected from hydroxyl-substituted hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, doicosylene, tricosylene, and tetraicosylene, or hexenylene, heptenylene, octenylene, nonenylene, desenylene, undesenylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, doicosylene, tricosylene, and tetraicosylene, and this group Most preferably bonded to an adjacent C(O) group or O group by a terminal C-atom, and

[0669] If present, R 7is optionally independently selected from hydroxyl-substituted hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, henicosyl, doicosyl, tricosyl, and tetraicosyl, or hexenyl, heptenyl, octenyl, nonenyl, desenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosyl, henicosyl, doicosyl, tricosyl, and tetraicosyl, wherein this group is most preferably bonded to an adjacent C(O) group by a terminal C-atom, and

[0670] m is 1 to 10, preferably 1, 2, 3, 4 or 5.

[0671] More preferably, X = O and,

[0672] R 6 is selected from hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, hexadecenylene, heptadecylene, octadecylene, nonadecylene, and eicosylene, and

[0673] If present, R 7 is selected from hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl hexadecenyl, heptadecyl, octadecyl, nonadecyl, and eicosyl, and

[0674] m is 1, 2, 3, 4, or 5.

[0675] Most preferably,

[0676] X = O and,

[0677] R 6 It is derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or resquerolic acid, and

[0678] If present, R 7 It is derived from oleic acid, ricinoleic acid, or stearic acid, and

[0679] m is 1, 2, 3, 4, or 5.

[0680] 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 chloroacetic acid chloride (EP 0283994, A. Baydar et al., Int. J. Cosmet. Sci., 1991, 13(4), 169-190) is described in the prior art. Further details are described in the Examples section.

[0681] In another preferred embodiment according to the present invention, a compound of formula (I) as defined above is provided, and

[0682] Preferably R of the following chemical formula 10 It is derived from esters of tertiary amino alcohols and esters of hydroxylated carboxylic acids, and in particular, the amino alcohols are N,N-dimethylethanolamine, N,N-dimethylpropanolamine, and N,N,N'-trimethylaminoethyl-ethanolamine.

[0683] -R 10 (-XC(O)-R 6 ) m -XC(O)- (XIII) and

[0684] -R 10 (-XC(O)-R 6 ) m -XC(O)-R 7 (XIIIa), more preferably

[0685] -R 10 -OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-

[0686] -R 10 -OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7

[0687] The esterification of alcohols containing tertiary amino groups with carboxylic acid chlorides is described in the prior art (US 2460182). Further details are described in the Examples section.

[0688] In another preferred embodiment, preferably R of the following chemical formula 10 It can be derived from amides of tertiary-primary amines, particularly N,N-dimethyl-1,3-propanediamine and N-methyl-N'-aminopropyl-piperazine, and tertiary-secondary amines, particularly N-methylpiperazine.

[0689] The synthesis of tertiary amino groups containing fatty amides starting from fatty acid esters (US 4221733) or free fatty acids (US 3768646) is described in the prior art. Further details are described in the Examples section.

[0690] In a preferred embodiment of the present invention, a compound of formula (I) is provided, wherein the moiety R of the compound of formula (I) as defined above is provided. 1 It is formed by the reaction of a halogenated carboxylic acid, preferably chloroacetic acid, with an OH-functionalized hydrocarbon. The synthesis of chloroacetic acid esters starting from chloroacetic acid or chloroacetic acid chloride and an OH-functionalized hydrocarbon is described in the prior art (R. Oda, Kogyo Kagaku Zasshi, 1933, 36, suppl. Binding 496-497, WO 0210257).

[0691] In another preferred embodiment according to the present invention, R of the compound of formula (I) as defined above. 1It is preferably formed by the reaction of a hydrocarbon epoxy derivative, which is a glycidyl ether or a glycidyl ether derivative, with a difunctional carboxylic acid. Such glycidyl ether or glycidyl ester derivatives can be synthesized from commercial or corresponding alcohol or carboxylic acid precursors. Preferred commercial epoxy derivatives are denacol type (Nagase) or helixy modifiers (Hexion), that is, corresponding derivatives based on 1,4-butanediol, glycerol, oligoglycerol, castor oil, and acid dimers. The synthesis of glycidyl ether or glycidyl ester is described in prior art (GB 763559, US 3766221, US 5420312, WO 2012041816).

[0692] In another preferred embodiment of the present invention, a compound of formula (I) is provided, wherein R of the compound of formula (I) as defined above is provided. 1 It is preferably formed by the reaction of an ester of a halogenated carboxylic acid, which is chloroacetic acid, with an epoxy-functionalized hydrocarbon, or by the reaction of an epoxy ester based on an epoxy-functionalized hydrocarbon with a difunctional carboxylic acid. The synthesis of this type of ester is described in US 2018 / 0016397.

[0693] Generally, the counterion A of the ammonium anion of a compound of chemical formula (I) as defined above. -is selected from monovalent to trivalent inorganic anions and monovalent to 30,000, preferably monovalent to 1,000, organic anions, and preferably selected from halides such as chloride, bromide, and iodide; carboxylates such as sulfate, phosphate, phosphonate, sulfonate, methosulfate, acetate, propionate, lactate, octanoate, 2-ethyl-hexanoate, dodecanoate, hexadecanoate, octadecanoate, oleate, ricinoleate, 12-hydroxy-octadecanoate, succinate, maleate, tartrate, and polyethercarboxylates, and fatty acid carboxylate polymers of the chemical formula type below.

[0694] R 1 [(-C(O)-XR 6 ) m -C(O)-XR 7 ] x or

[0695] R 1 [(XC(O)-R 6 ) m -XC(O)-R 7 ] x ,

[0696] Here, R 1 or at least one R 7 One of them, or R 1 and at least one R 7 It has one or more carboxylate groups,

[0697] Preferably X = O, and

[0698] especially

[0699] - OC(O)-R 6 (-XC(O)-R 6 ) m-1 -XC(O)-R 7 , preferably - OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7It is a linear polymer of the type fatty acid carboxylate, and

[0700] It is a branched linear polymer of fatty acid carboxylates, and

[0701] That is, it is a branched linear polymer of fatty acid carboxylates derived from a branched poly fatty acid structure, and in particular derived from a partial ester of a polyfunctional carboxylic acid and castor oil or lesquerella oil as follows, wherein the polyfunctional carboxylic acid is specifically the dicarboxylic acid succinic acid and maleic acid, e.g. as follows, and

[0702]

[0703] One R =

[0704]

[0705] The remaining 2 R =

[0706]

[0707] It is a fatty acid carboxylate dendritic polymer, and

[0708] That is, derived from a dendritic poly fatty acid structure,

[0709] Or is of the type below,

[0710] XR 6 (-C(O)-XR 6 ) m-1 -C(O)-XR 7 or

[0711] R 6 (-C(O)-XR 6 ) m-1 -C(O)-XR 7

[0712] R in the two latter types 7 The group has at least one anionic carboxylate group, and

[0713] or the type below

[0714] R 1 [(-C(O)-X-R6) m -C(O)O - ] x

[0715] Here, X, R 1 , R 6 , R 7 , m and x are as defined above, and

[0716] Here, the counterion A of this group - is preferably 1 to 50 valent, more preferably 1 to 10 valent, even more preferably 1 to 5 valent, most preferably 5 valent, 4 valent, 3 valent, 2 valent, or 1 valent anion, and

[0717] Or the counteranion is selected from the group consisting of carboxylate anions based on poly(acrylic acid) homopolymers and copolymers and poly(itaconic acid) homopolymers and copolymers, and

[0718] Here, the anion of this group is preferably divalent to 30,000 valent, more preferably divalent to 1,000 valent, even more preferably 10 valent to 1,000 valent, even more preferably 50 valent to 1,000 valent, and most preferably 100 valent to 1,000 valent anion, and

[0719] Preferably derived from a fatty acid carboxylate polymer of the following type, which is a single-chain molecule without esterified OH-substituents, and

[0720] - OC(O)-R 6 (-XC(O)-R 6 ) m-1 -XC(O)-R 7

[0721] Or preferably derived from the fatty acid carboxylate polymers of the following types defined above, which are branched or dendrimer (self-repeating) motif-containing carboxylates derived particularly from 2,2'-dihydroxymethylpropanoic acid.

[0722] R 1 [(-C(O)-X-R6) m -C(O)O - ] x

[0723] The synthesis of the dendrimer structure of 2,2'-di-hydroxymethylpropanoic acid is described in US 2016 / 0102179.

[0724] In a further preferred embodiment according to the present invention, the counterion A of the compound according to the present invention of formula (I) as defined above. - is a monovalent to trivalent inorganic anion and a monovalent to 30,000valent, preferably monovalent to 1,000valent organic anion, which is selected from halogenated anions such as chloride, bromide, and iodide; carboxylate anions such as sulfate, phosphate, phosphonate, sulfonate, methosulfate, acetate, propionate, lactate, octanoate, 2-ethyl-hexanoate, dodecanoate, hexadecanoate, octadecanoate, oleate, ricinolate, 12-hydroxy-octadecanoate, succinate, maleate, tartrate, and polyethercarboxylate, and fatty acid carboxylate polymers of the following types.

[0725] R 1 [(-C(O)-XR 6 ) m -C(O)-XR 7 ] x or

[0726] R 1 [(XC(O)-R 6 ) m -XC(O)-R 7 ] x ,

[0727] Here, R 1 or at least one R 7 One of them, or R 1 and at least one R 7 It has one or more carboxylate groups,

[0728] Preferably X = O, and

[0729] especially

[0730] It is a linear polymer of the following type of fatty acid carboxylate, and

[0731] - OC(O)-R 6 (-XC(O)-R 6 ) m-1 -XC(O)-R 7 , preferably

[0732] - OC(O)-R 6 -(OC(O)-R 6 ) m -OC(O)-R 7 ,

[0733] It is a branched linear polymer of fatty acid carboxylates, and

[0734] That is, it is a branched linear polymer of fatty acid carboxylate derived from a branched poly fatty acid structure, and in particular derived from a partial ester of a polyfunctional carboxylic acid and castor oil or lesquerella oil as follows, wherein the polyfunctional carboxylic acid is the dicarboxylic acid succinic acid and maleic acid, for example as follows,

[0735]

[0736] One R =

[0737]

[0738] The remaining 2 R =

[0739]

[0740] It is a fatty acid carboxylate dendritic polymer, and

[0741] That is, derived from a dendritic poly fatty acid structure,

[0742] Or is of the type below,

[0743] XR 6 (-C(O)-XR 6 ) m-1 -C(O)-XR 7 or

[0744] R 6 (-C(O)-XR 6 ) m-1 -C(O)-XR 7

[0745] R in the two latter types 7 The group has at least one anionic carboxylate group, and

[0746] or the type below

[0747] R 1 [(-C(O)-X-R6) m -C(O)O - ] x

[0748] Here, X, R 1 , R 6 , R 7 , m, and x are as defined above, and the counterion A of this group - is preferably 1 to 50 valent, more preferably 1 to 10 valent, even more preferably 1 to 5 valent, most preferably 5 valent, 4 valent, 3 valent, 2 valent, or 1 valent anion, and

[0749] or selected from the group consisting of carboxylate anions based on poly(acrylic acid) homopolymers and copolymers and poly(itaconic acid) homopolymers and copolymers, wherein the anion of this group is preferably divalent to 30,000 valent, more preferably divalent to 1,000 valent, even more preferably 10 valent to 1,000 valent, even more preferably 50 valent to 1,000 valent, and most preferably 100 valent to 1,000 valent anion.

[0750] Preferably derived from a fatty acid carboxylate polymer of the following type, which is a single-chain molecule without esterified OH-substituents, and

[0751] - OC(O)-R 6 (-XC(O)-R 6 ) m-1 -XC(O)-R 7

[0752] Or preferably derived from the fatty acid carboxylate polymers of the following types defined above, which are branched or dendrimer (self-repeating) motif-containing carboxylates derived particularly from 2,2'-dihydroxymethylpropanoic acid.

[0753] R 1 [(-C(O)-X-R6) m -C(O)O - ] x

[0754] The desired counterion can be incorporated into the quaternized material during the quaternization process or by anion exchange. In this context, it is possible to produce target materials and alkali metal halides, particularly NaCl, NaBr, KCl, and KBr, by exchanging the inorganic counterion of a fatty acid or fatty acid polymer with an initial inorganic counterion-containing material, such as a fatty acid carboxylate or fatty acid carboxylate polymer, by adding an alkali salt, preferably sodium and potassium salt, to the organic counterion, such as chlorine or bromine.

[0755] In a preferred embodiment according to the present invention, X in formula (III) and / or (IV) is O, and preferably, the compound according to the present invention does not contain an amide group.

[0756] Amid bonds are generally more stable against hydrolysis, but they also impart structural rigidity compared to ester groups. Therefore, according to this embodiment, the X group represents an oxygen atom in all structures of formula (III) and / or (IV) present in the compound, and it is preferable that the compound does not contain any amide groups.

[0757] In another preferred embodiment, the group R present in the cation structures of formulas (I) and (II) in the compound according to the present invention 1 , R 2 , R 3 , R 4 , R 5At least one of them contains at least one moiety of the following chemical formula, and

[0758] R 1* [(-OC(O)- R 6 ) m -OC(O)-]2,

[0759] Here, R 1* It is a divalent C1-C100 hydrocarbon radical, preferably a C1-C12 alkylene, most preferably a methylene, ethylene, 1,3-propylene, 1,4-butylene, 1,6-hexylene, 1,2-propylene, or 1,3-butylene radical, and

[0760] m is independently selected from 1 to 12, and

[0761] R 6 is as defined above.

[0762] Here, the moiety of the chemical formula below is preferably formed from an alkylene diol, and more preferably from an α,o-alkylene diol such as 1,2-ethanediol, 1,3-propanediol, 1,4-butanediol and 1,6-hexanediol by sequential or block unit ester chain formation.

[0763] R 1* [(-OC(O)- R 6 ) m -OC(O)-]2

[0764] Regardless of whether a single hydroxy-substituted carboxylic acid is added in a repeating manner, or whether an estolide chain having a carboxylic acid group reacts with this diol, if an excess of the carboxylic acid reactant is used, the diol is esterified mainly at both ends in the same way. That is, a symmetric structure of the chemical formula below is obtained.

[0765] R 1* [(-OC(O)- R 6 ) m -OC(O)-]2

[0766] Therefore, R 1*The structure of the group generally corresponds directly to the alkylene diol applied as a starting material.

[0767] According to the present invention, R 1* It is a divalent C2-C100 hydrocarbon radical, which includes all types of linear, branched, and cyclic aliphatic and aromatic divalent hydrocarbon groups, such as alkylene, alkenylene, alkynylene, and aromatic structures, such as phenylene.

[0768] A C1-C12 alkylene diol is a preferred starting material, R 1* It is preferably a C1-12 alkylene group, more preferably methylene, ethylene, n-propylene, n-butylene, n-pentylene, n-hexylene, even more preferably a methylene, ethylene, n-propylene or n-butylene or n-hexylene group.

[0769] According to this embodiment, m is selected independently, but it is desirable that all m of the structure below be the same because the moiety is generally symmetric.

[0770] R 1* [(-OC(O)- R 6 ) m -OC(O)-]2

[0771] m is independently 1 to 6, more preferably 1 to 4, even more preferably all m are the same and selected from 1 to 6, and most preferably all m are the same and selected from 1 to 4.

[0772] According to a specific example, R 6 is as defined above, but preferably R 6The radical is selected from linear alkylene groups and linear alkenylene groups, in particular linear C6-C24 alkylene groups, e.g., heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, doicosylene, tricosylene and tetracosylene, or linear C6-C24 alkenylene groups, e.g., heptenylene, octenylene, nonenylene, decenylene, undecenylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecenylene, nonadecenylene, The groups are eicosenylene, henicosenylene, doicosenylene, tricosenylene, and tetraicosenylene, wherein the group is most preferably bonded to an adjacent C(O) group by a terminal C-atom.

[0773] More preferably, R 6 is derived from a C7-C25 fatty acid having one hydroxyl group as a substituent, and more preferably R 6 It is derived from ricinoleic acid, resquerolic acid, 10-hydroxyoctadecanic acid, 12-hydroxyoctadecanic acid, 14-hydroxytetradecanoic acid, 10-hydroxystearic acid, and 12-hydroxystearic acid.

[0774] Most preferably R 6 It is derived from ricinoleic acid.

[0775] In general, all R of the moiety in the chemical formula below 6 It is desirable that the same beneficiary be present in this specific example and any other specific example.

[0776] R 1* [(-OC(O)- R 6 ) m -OC(O)-]2

[0777] In a further preferred embodiment, R present in the cation structures of formulas (I) and (II) in the compounds according to the present invention 1 , R 2 , R3 , R 4 , R 5 At least one of the groups contains at least one moiety of the following chemical formula, and

[0778] R 1* [(-OC(O)- R 6 ) m -OC(O)-]2

[0779] Here, R 1* It is selected from methylene, ethylene, 1,3-propylene, 1,4-butylene, 1,6-hexylene, 1,2-propylene, and 1,3-butylene, and

[0780] R 6 is derived from C8-C24 monocarboxy-monohydroxycarboxylic acids, in particular from ricinoleic acid, 12-hydroxy stearic acid, resquerolic acid, and 11-hydroxy-undecanic acid, and m is independently selected from 1 to 6.

[0781] According to this embodiment, all R 6 It is desirable that it is derived from the same carboxylic acid and that all ms of the structure are identical.

[0782] In a further preferred embodiment, in the compound according to the present invention, the group R present in the cation structure of formulas (I) and (II) 1 , R 2 , R 3 , R 4 , R 5 At least one of them contains at least one moiety of the following chemical formula, and

[0783] R 1* [(-OC(O)- R 6 ) m -OC(O)-]2

[0784] This is represented by one of the structural formulas below.

[0785] -C(O)-O-(mono or oligo C8-C24 hydroxyl fatty acid)-C(O)-O-(C2-C10 hydrocarbon)-OC(O)-(mono or oligo C8-C24 hydroxyl fatty acid) -OC(O)-

[0786] Here,

[0787] - C2-C10 hydrocarbons are C2-C10 hydrocarbylenes, and are derived particularly from ethylene glycol, 1,3-propylene glycol, 1,4-butanediol, 1,6-hexanediol, 1,2-propylene glycol, and 1,3-butanediol, and

[0788] - Mono or oligo C8-C24 hydroxy fatty acids are derived from C8-C24 hydroxy-substituted carboxylic acid monomers or oligomers of up to 20 C8-C24 hydroxy-substituted carboxylic acid monomers formed through esterification, particularly derived from mono or oligoricinoleic acid, and the degree of oligomerization is 2 to 20, preferably 2 to 10, more preferably 2 to 6, even more preferably 2 to 4.

[0789] These compounds are exemplified by the following structural formulas.

[0790]

[0791] R:

[0792]

[0793] and

[0794]

[0795] R:

[0796]

[0797] In another additional preferred embodiment, the group R present in the cation structures of formulas (I) and (II) in the compound according to the present invention 1 , R 2 , R 3 , R 4 , R 5At least one of them contains at least one moiety of the following chemical formula, and

[0798] R 1* [(-OC(O)- R 6 ) m -OC(O)-R 7 *-]2

[0799] Here

[0800] R 1* , R 6 and m are as defined above, and

[0801] R 7* is a C1-C12 alkylene group, preferably a methylene, ethylene, propylene, or butylene group.

[0802] In these specific examples, the estolide chain of the moiety shown above is generally bonded to an alkylene group after the formation of an estolide chain structure included in the moiety of the chemical formula below, and

[0803] R 1* [(-OC(O)- R 6 ) m -OC(O)-R 7* -]2

[0804] The terminal hydroxyl group of the chain structure reacts with carboxylic acids or carboxylic acid chlorides having functionalized alkyl chains, and in particular with halo-alkyl carboxylic acid chlorides. By this, R 7* A precursor of the group is attached to the structure, and upon further functionalization, a moiety of the chemical formula below is obtained.

[0805] R 1* [(-OC(O)- R 6 ) m -OC(O)-R 7* -]2

[0806] According to this specific example, R 7* is a C1-C12 alkylene group, preferably a methylene, ethylene, propylene, or butylene group, and most preferably a methylene group.

[0807] For example, the methylene group R 7* It can be obtained by the esterification and subsequent functionalization of the terminal hydroxyl group of an estolide chain with chloroacetic acid chloride, for example, by using the chloro group as a leaving group in the quaternization reaction of a tertiary amine.

[0808] In a further preferred embodiment, R present in the cation structures of formulas (I) and (II) in the compounds according to the present invention 1 , R 2 , R 3 , R 4 , R 5 At least one of the groups contains at least one moiety of the following chemical formula, and

[0809] R 1* [(-OC(O)- R 6 ) m -OC(O)-R 7* -]2

[0810] Here

[0811] R 1* It is selected from methylene, ethylene, 1,3-propylene, 1,4-butylene, and 1,6-hexylene, and

[0812] R 6 It is derived from C8-C24 monocarboxy-monohydroxycarboxylic acids, in particular from ricinoleic acid, 12-hydroxy stearic acid, resquerolic acid, and 11-hydroxy-undecanic acid, and

[0813] m is independently selected from 1 to 6, and

[0814] R 7* It is selected from methylene and ethylene.

[0815] In a further preferred embodiment, in the compound according to the present invention, the group R present in the cation structure of formulas (I) and (II) 1 , R 2 , R 3 , R 4 , R 5At least one of them contains at least one moiety of the following chemical formula, and

[0816] R 1* [(-OC(O)- R 6 ) m -OC(O)-R 7* -]2

[0817] This is represented by one of the structural formulas below.

[0818] i) -CH2-C(O)-O-(mono or oligo C8-C24 hydroxyl fatty acid)-C(O)-O-(C2-C10 hydrocarbon)-OC(O)-(mono or oligo C8-C24 hydroxyl fatty acid)-OC(O)-CH2-

[0819] or

[0820] ii) -CH2CH2-C(O)-O-(mono or oligo C8-C24 hydroxy fatty acid)-C(O)-O-(C2-C10 hydrocarbon)-OC(O)-(mono or oligo C8-C24 hydroxy fatty acid)-OC(O)-CH2CH2-,

[0821] Here

[0822] - C2-C10 hydrocarbons are C2-C10 hydrocarbylene groups, and are derived particularly from ethylene glycol, 1,3-propylene glycol, 1,4-butanediol, 1,6-hexanediol, 1,2-propylene glycol, and 1,3-butanediol, and

[0823] - Mono or oligo C8-C24 hydroxy fatty acids are derived from C8-C24 hydroxy-substituted carboxylic acid monomers or oligomers of up to 20 C8-C24 hydroxy-substituted carboxylic acid monomers formed through esterification, particularly derived from mono or oligoricinoleic acid, with a degree of oligomerization of 2 to 20, preferably 2 to 10, more preferably 2 to 6, and even more preferably 2 to 4.

[0824] These compounds are exemplified by the structural formula below.

[0825]

[0826] R:

[0827]

[0828] and

[0829]

[0830] R:

[0831]

[0832] In a further preferred embodiment, in the compound according to the present invention, at least one moiety of the following chemical formula is a terminal R 7* It is bonded to a quaternary N atom in one or both of the groups.

[0833] R 1* [(-OC(O)- R 6 ) m -OC(O)-R 7* -]2

[0834] Accordingly, according to this embodiment, the compound according to the present invention contains at least one moiety of the following chemical formula, and

[0835] R 1* [(-OC(O)- R 6 ) m -OC(O)-R 7* -N + ]2

[0836] Here, the two terminals R 7* The group is bonded to a quaternary N atom, and / or is bonded to at least one moiety of the formula below, and

[0837] N + -R 7* -C(O)-O-(R 6 -C(O)-O) m -R1*- * (-OC(O)- R 6 ) m -OC(O)-R 7 *-

[0838] Here, one terminal R 7* The ion is bonded to the quaternary N atom.

[0839] Additionally, it is preferable that one or two quaternary N atoms each have two groups independently selected from methyl, ethyl, propyl, and butyl groups.

[0840] More preferably, one or two quaternary N atoms each have two methyl substituents, even more preferably the fourth substituent is an alkyl group substituted by an alkyl amino group or an ammonium group, and most preferably the fourth substituent is selected from an ethylene dimethylammonium group, a propylene dimethylammonium group, a butylene dimethylammonium group, or a hexylene dimethylammonium group.

[0841] 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, a quaternary ammonium group containing one methyl group can be derived from N,N'-dimethylpiperazine.

[0842] In another preferred embodiment according to the present invention, at least one moiety of the following formula is R 7* One or both of the terminal groups are bonded to a quaternary N atom, and the compound is a di-quat or tetra-quat compound.

[0843] R 1* [(-OC(O)- R 6 ) m -OC(O)-R 7* -]2

[0844] Here, preferably, two terminal Rs 7* The group is bonded to a quaternary N atom, and more preferably to two terminal Rs. 7* The group is bonded to a quaternary N atom having three alkyl substituents each having 1 to 12 carbon atoms, or the formula -N + (CH3)2-ALK-N +It is bonded to a quaternary N atom represented by (CH3)3, where ALK is a divalent alkylene group having 1 to 12 carbon atoms, preferably a linear alkylene group.

[0845] According to a specific example, two terminal R 7* When a group is bonded to a quaternary N atom having three alkyl substituents each having 1 to 12 carbon atoms, it is preferable that the alkyl substituents be selected from methyl, ethyl, propyl, and butyl groups, and most preferably, all three substituents are methyl groups.

[0846] 2 terminal Rs 7* The chemical formula -N as defined above. + (CH3)2-ALK-N + When bonded to a quaternary N atom represented by (CH3)3, it is preferable that the group ALK be a methylene group, an ethylene group, an n-propyl group, an n-butylene group, or an n-hexylene group.

[0847] In a further preferred embodiment, the compound according to the present invention comprises at least two moieties of the following chemical formula, and

[0848] R 1* [(-OC(O)- R 6 ) m -OC(O)-R 7* -]2

[0849] Here, the moiety is connected to each other through di-quaternary ammonium alkylene groups of the following structure, and

[0850] -N + (CH3)2-ALK-N + (CH3)2-

[0851] Here, ALK is a divalent alkylene group having 1 to 12 carbon atoms, preferably a linear alkylene group.

[0852] Preferably, the compound comprises more than 4, more preferably more than 6, and even more preferably more than 8 moiety of the following formula, and the following formulas are connected through diammonium alkylene groups.

[0853] R 1* [(-OC(O)- R 6 ) m -OC(O)-R 7* -]2

[0854] More preferably, the ALK group is independently selected from ethylene, n-propylene, n-butylene, or n-hexylene, and more preferably, all ALK groups are the same type of alkylene group.

[0855] In another preferred embodiment of the compound according to the present invention, R present in the cation structures of formulas (I) and (II) 1 , R 2 , R 3 , R 4 , R 5 At least one of the groups contains at least one moiety of the following chemical formula, and

[0856] - ([-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])-

[0857] Here, R 6 is as defined above, and

[0858] l is an integer independently selected from 0 to 20, more preferably 1 to 12, and even more preferably 2 to 10, and

[0859] L is a divalent hydrocarbon radical that can have 1 to 30 carbon atoms, which is -O-, -S-, -NH-, -C(O)-, -C(S)- and tertiary amino groups ( It may optionally contain one or more groups selected from ), and

[0860] Preferably, L is a divalent alkylene or alkenylene radical having 1 to 30 carbon atoms, and

[0861] More preferably, L is selected from methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, ethenylene, propenylene, butylene, pentenylene, hexenylene, heptylene, octenylene, and nonenylene, and

[0862] Most preferably, L is selected from methylene, ethylene, ethenylene, or butenylene.

[0863] According to this specific example, R 6 It is preferably derived independently from C8-C24 monocarboxy-monohydroxycarboxylic acids, in particular from ricinoleic acid, 12-hydroxy stearic acid, resquerolic acid and 11-hydroxy-undecanic acid.

[0864] In a preferred embodiment of the compound according to the present invention,

[0865] R present in the cation structures of chemical formulas (I) and (II) 1 , R 2 , R 3 , R 4 , R 5 At least one of the groups contains at least one moiety of the following chemical formula, and

[0866] - ([-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])-

[0867] Here, L and l are as defined above, and

[0868] R 6is independently derived from C8-C24 monocarboxy-monohydroxycarboxylic acids, preferably derived from ricinoleic acid, 12-hydroxy stearic acid, resquerolic acid, 11-hydroxy-undecanic acid, and most preferably R 6 It is derived from ricinoleic acid.

[0869] 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 to 6, and R 6 It is derived from ricinoleic acid.

[0870] In a preferred embodiment of the compound according to the present invention, R present in the cation structure of formulas (I) and (II) 1 , R 2 , R 3 , R 4 , R 5 At least one of the groups contains at least one moiety of the following chemical formula, and

[0871] - ([-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])-

[0872] Here, L is selected from methylene, ethylene, and ethanyllene, and

[0873] R 6 It is derived from ricinoleic acid, and

[0874] l is independently selected from 0, 1, 2 and 3, and the sum of l is in the range of 0 to 4.

[0875] Preferably, L is an ethylene group, and R 6 is derived from ricinoleic acid, and l is independently selected from 0 or 1.

[0876] In a preferred embodiment of the compound according to the present invention, R present in the cation structure of formulas (I) and (II) 1 , R 2 , R 3 , R 4 , R 5 At least one of the groups contains at least one moiety of the following chemical formula, and

[0877] - ([-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])-

[0878] This is represented by the structure below.

[0879] -OC(O)-(mono or oligo C8-C24 hydroxy fatty acid)-OC(O)-(C1-C12 hydrocarbon)-C(O)-O-(mono or oligo C8-C24 hydroxy fatty acid)-C(O)-O-

[0880] Here

[0881] - The C1-C12 hydrocarbon is a C1-C12 hydrocarbylene group, preferably a C2 to C10 hydrocarbylene group, and

[0882] - Mono or oligo C8-C24 hydroxy fatty acids are groups derived from C8-C24 hydroxy-substituted carboxylic acid monomers or oligomers of up to 20 C8-C24 hydroxy-substituted carboxylic acid monomers formed through esterification, and the degree of oligomerization is 2 to 20, preferably 2 to 10, more preferably 2 to 6, and even more preferably 2 to 4.

[0883] The C1-C12 hydrocarbon group is preferably derived from succinic acid, maleic acid, itaconic acid, adipic acid, sebacic acid, or dodecandioic acid, and

[0884] The mono or oligo C8-C24 hydroxy fatty acid group is preferably derived from mono or oligo ricinoleic acid, and the degree of oligomerization is 2 to 20, preferably 2 to 10, more preferably 2 to 6, and even more preferably 2 to 4.

[0885] Compounds of this structure are exemplified as follows.

[0886]

[0887] R:

[0888]

[0889] In a preferred embodiment of the compound according to the present invention, R present in the cation structure of formulas (I) and (II) 1 , R 2 , R 3 , R 4 , R 5 At least one of the groups contains at least one moiety of the following chemical formula, and

[0890] - ([-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

[0891] Here, L, l, R 6 is as defined above, and

[0892] R 12 is a C1 to C12 linear or branched hydrocarbylene group that may contain up to 4 -O- groups and up to 4 tertiary amino groups, which is bonded to the -O- group of an ester group at one end and to a quaternary N atom at the other end, and

[0893] Preferably R 12 It is derived from tertiary amino alcohols, particularly amino alcohols having the structure below.

[0894]

[0895] Preferably, L, I, and R 6 is as defined above, and R 12 is selected from -CH2CH2- and CH2CH2CH2-.

[0896] More preferably, l is independently selected from the range of 0 to 6, preferably 1 to 6, and more preferably 2 to 6.

[0897] R 6 It is preferably derived from ricinoleic acid, and

[0898] R 12 It is preferably selected from -CH2CH2- and -CH2CH2CH2-.

[0899] In addition, the present invention relates to a method for synthesizing a compound of formula (I) as defined in all prior embodiments.

[0900] R 1 (-F) x (I)

[0901] Here, the alkyl halide reacts with a tertiary amine containing at least one moiety of the chemical formula below, and

[0902] (-XC(O)-R 6 ) m -XC(O)- (III) or

[0903] (-C(O)-XR 6 ) m -C(O)-X- (IV), preferably containing at least one moiety of the following chemical formula,

[0904] (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa) or

[0905] (-C(O)-XR 6 ) m -C(O)-XR 7 (IVa),

[0906] or

[0907] Preferably, an ester of a halogen carboxylic acid, which is chloroacetic acid, and an alcohol or epoxide as defined above react with a tertiary amine containing at least one moiety of the chemical formula below, and

[0908] (-XC(O)-R 6 ) m -XC(O)- (III) or

[0909] (-C(O)-XR 6 ) m -C(O)-X- (IV), preferably containing at least one moiety of the following chemical formula,

[0910] (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa) or

[0911] (-C(O)-XR 6 ) m -C(O)-XR 7 (IVa),

[0912] or

[0913] Epoxy-functionalized ethers and esters, preferably glycidyl ethers and esters, are reacted with an alcohol or carboxylic acid as defined above in the presence of a tertiary amine containing at least one moiety of the formula below and an acid, and

[0914] (-XC(O)-R 6 ) m -XC(O)- (III) or

[0915] (-C(O)-XR 6 ) m -C(O)-X- (IV), preferably containing at least one moiety of the following chemical formula,

[0916] (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa) or

[0917] (-C(O)-XR 6 ) m -C(O)-XR 7 (IVa) ,

[0918] or

[0919] A hydrocarbon containing a tertiary amino group reacts with an ester of a halogen carboxylic acid as defined above, containing at least one moiety of the chemical formula below, and

[0920] (-XC(O)-R 6 ) m -XC(O)- (III) or

[0921] (-C(O)-XR 6 ) m -C(O)-X- (IV), preferably containing at least one moiety of the following chemical formula,

[0922] (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa) or

[0923] (-C(O)-XR 6 ) m -C(O)-XR 7 (IVa),

[0924] or

[0925] Hydrocarbons containing a tertiary amino group react with epoxy-functionalized ethers and esters as defined above containing at least one of the chemical formulas below in the presence of an acid, and

[0926] (-XC(O)-R 6 ) m -XC(O)- (III) or

[0927] (-C(O)-XR 6 ) m -C(O)-X- (IV), preferably containing at least one moiety of the following chemical formula,

[0928] (-XC(O)-R 6 )m -XC(O)-R 7 (IIIa) or

[0929] (-C(O)-XR 6 ) m -C(O)-XR 7 (IVa)

[0930] Here, X, R 6 , R 7 , m and x are as defined above.

[0931] According to these specific examples, preferably

[0932] X=O and,

[0933] R 6 is optionally selected from hydroxyl-substituted hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, doicosylene, tricosylene and tetraicosylene, or hexenylene, heptenylene, octenylene, nonenylene, desenylene, undesenylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, doicosylene, tricosylene and tetraicosylene, and this group Preferably bonded to an adjacent C(O) group by a terminal C-atom, and

[0934] If present, R 7The group is optionally selected from hydroxyl-substituted hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, henicosyl, doicosyl, tricosyl, and tetraicoisyl, or hexenyl, heptenyl, octenyl, nonenyl, desenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosyl, henicosyl, doicosyl, tricosyl, and tetraicosyl, wherein the group is preferably bonded to an adjacent C(O) group by a terminal C-atom, and

[0935] m is 1 to 10, preferably 1, 2, 3, 4 or 5.

[0936] Even more preferably, X = O and,

[0937] R 6 is selected from hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, hexadecenylene, heptadecylene, octadecylene, nonadecylene, and eicosylene, and

[0938] If present, R 7 is selected from hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl hexadecenyl, heptadecyl, octadecyl, nonadecyl, and eicosyl, and

[0939] m is 1, 2, 3, 4, or 5.

[0940] According to these embodiments, most preferably,

[0941] X = O and,

[0942] R 6 It is derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or resquerolic acid, and

[0943] If present, R 7 It is derived from oleic acid, ricinoleic acid, or stearic acid, and

[0944] m is 1, 2, 3, 4, or 5.

[0945] In a preferred embodiment according to the present invention, R 1 This quaternized nitrogen atom N + R through 3 , R 4 and R 5 A method for synthesizing a compound of formula (I) is provided, which is connected to and contains at least one moiety of formula (III) or formula (IV), preferably formula (IIIa) or formula (IVa), and

[0946] R 1 (-F) x (I)

[0947] (-XC(O)-R 6 ) m -XC(O)- (III),

[0948] (-C(O)-XR 6 ) m -C(O)-X- (IV),

[0949] (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa),

[0950] (-C(O)-XR 6 ) m -C(O)-XR 7 (IVa) ,

[0951] Here

[0952] The alkyl halide reacts with a tertiary amine containing at least one moiety of the chemical formula below, and

[0953] (-XC(O)-R 6 ) m -XC(O)- (III) or

[0954] (-C(O)-XR 6 ) m -C(O)-X- (IV), preferably containing at least one moiety of the following chemical formula,

[0955] (-XC(O)-R6 ) m -XC(O)-R 7 (IIIa) or

[0956] (-C(O)-XR 6 ) m -C(O)-XR 7 (IVa),

[0957] or

[0958] Preferably, an ester of a halogen carboxylic acid, which is chloroacetic acid, and an alcohol or epoxide as defined above react with a tertiary amine containing at least one moiety of the chemical formula below, and

[0959] (-XC(O)-R 6 ) m -XC(O)- (III) or

[0960] (-C(O)-XR 6 ) m -C(O)-X- (IV), preferably containing at least one moiety of the following chemical formula and

[0961] (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa) or

[0962] (-C(O)-XR 6 ) m -C(O)-XR 7 (IVa),

[0963] or

[0964] Epoxy-functionalized ethers and esters, preferably glycidyl ethers and esters, react with an alcohol or carboxylic acid as defined above in the presence of an acid and a tertiary amine containing at least one moiety of the formula below, and

[0965] (-XC(O)-R 6 ) m -XC(O)- (III) or

[0966] (-C(O)-XR 6 ) m-C(O)-X- (IV), preferably containing at least one moiety of the following chemical formula,

[0967] (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa) or

[0968] (-C(O)-XR 6 ) m -C(O)-XR 7 (IVa) ,

[0969] or

[0970] A hydrocarbon containing a tertiary amino group reacts with an ester of a halogen carboxylic acid containing at least one moiety of the chemical formula below as defined above, and

[0971] (-XC(O)-R 6 ) m -XC(O)- (III) or

[0972] (-C(O)-XR 6 ) m -C(O)-X- (IV), preferably containing at least one moiety of the following chemical formula,

[0973] (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa) or

[0974] (-C(O)-XR 6 ) m -C(O)-XR 7 (IVa),

[0975] or

[0976] A hydrocarbon containing a tertiary amino group reacts in the presence of an acid with an epoxy-functionalized ether and ester containing at least one moiety of the chemical formula below as defined above, and

[0977] (-XC(O)-R 6 ) m -XC(O)- (III) or

[0978] (-C(O)-XR 6 ) m -C(O)-X- (IV), preferably containing at least one moiety of the following chemical formula,

[0979] (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa) or

[0980] (-C(O)-XR 6 ) m -C(O)-XR 7 (IVa)

[0981] Here, X, R 6 , R 7 , m and x are as defined above.

[0982] According to this embodiment, preferably

[0983] X=O and,

[0984] R 6 is optionally selected from hydroxyl-substituted hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, doicosylene, tricosylene, and tetracoylene, or hexenylene, heptenylene, octenylene, nonenylene, desenylene, undesenylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, doicosylene, tricosylene, and tetraicosylene, and this group Most preferably bonded to an adjacent C(O) group or O group by a terminal C-atom, and

[0985] If present, R 7is optionally selected from hydroxyl-substituted hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, henicosyl, doicosyl, tricosyl and tetraicosyl, or hexenyl, heptenyl, octenyl, nonenyl, desenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosyl, henicosyl, doicosyl, tricosyl and tetraicosyl, wherein this group is most preferably bonded to an adjacent C(O) group by a terminal C-atom, and

[0986] m is 1 to 10, preferably 1, 2, 3, 4 or 5.

[0987] More preferably, X = O and,

[0988] R 6 is selected from hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, hexadecenylene, heptadecylene, octadecylene, nonadecylene, and eicosylene, and

[0989] If present, R 7 is selected from hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl hexadecenyl, heptadecyl, octadecyl, nonadecyl, and eicosyl, and

[0990] m is 1, 2, 3, 4, or 5.

[0991] Most preferably in this embodiment,

[0992] X = O and,

[0993] R 6 It is derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or resquerolic acid, and

[0994] If present, R 7 It is derived from oleic acid, ricinoleic acid, or stearic acid, and

[0995] m is 1, 2, 3, 4, or 5.

[0996] In another preferred embodiment of the present invention, R 1 N is a quaternized nitrogen atom + A method for synthesizing a compound of formula (I) is provided, which is connected to and contains at least one moiety among formulas (XIII), (XIV), (XIIIa) or (XIVa), and

[0997] R 1 (-F) x (I)

[0998] -R 10 (-XC(O)-R 6 ) m -XC(O)- (XIII)

[0999] -R 10 (-C(O)-XR 6 ) m -C(O)-X- (XIV), preferably

[1000] -R 10 (-XC(O)-R 6 ) m -XC(O)-R 7 (XIIIa)

[1001] -R 10 (-C(O)-XR 6 ) m -C(O)-XR 7 (XIVa)

[1002] Here,

[1003] R 1 This quaternized nitrogen atom N + Connected to, and R 1 (-F) x To obtain a compound containing at least one moiety of formulas (XIII), (XIV), (XIIIa) or (XIVa), an alkyl halide reacts with a tertiary amine containing at least one moiety of formulas (XIII), (XIV), (XIIIa) or (XIVa), and

[1004] or

[1005] To obtain the compound mentioned above, an ester of a halogen carboxylic acid, preferably chloroacetic acid, and an alcohol or epoxide are reacted with a tertiary amine having at least one moiety of formulas (XIII), (XIV), (XIIIa) or (XIVa), and

[1006] or

[1007] To obtain the compound mentioned above, an epoxy-functionalized ether and ester formed from an alcohol or carboxylic acid as defined above, preferably a glycidyl ether and ester, is reacted with a tertiary amine containing at least one moiety of formula (XIII), (XIV), (XIIIa) or (XIVa), and

[1008] or

[1009] To obtain the compound mentioned above, a hydrocarbon containing a tertiary amino group reacts with an ester of a halogenated carboxylic acid containing at least one moiety of formulas (XIII), (XIV), (XIIIa), or (XIVa), and

[1010] or

[1011] To obtain the compounds mentioned above, a hydrocarbon containing a tertiary amino group is reacted in the presence of an acid with an epoxy-functionalized ether and ester having at least one moiety of formula (XIII), (XIV), (XIIIa), or (XIVa), as defined above, where R 10 , X, R 6 , R 7 , m and x are as defined above.

[1012] According to this embodiment, preferably

[1013] X=O and,

[1014] R 6is optionally independently selected from hydroxyl-substituted hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, doicosylene, tricosylene and tetraicosylene, or hexenylene, heptenylene, octenylene, nonenylene, desenylene, undesenylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, doicosylene, tricosylene and tetraicosylene, wherein this The group is most preferably bonded to an adjacent C(O) group or O group by a terminal C-atom, and

[1015] If present, R 7 is optionally independently selected from hydroxyl-substituted hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, henicosyl, doicosyl, tricosyl and tetraicosyl, or hexenyl, heptenyl, octenyl, nonenyl, desenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosyl, henicosyl, doicosyl, tricosyl, and tetraicosyl, and this group is most preferably bonded to an adjacent C(O) group by a terminal C-atom, and

[1016] R 1 is an unsubstituted C1-C8 alkylene group that does not contain a functional group, or R 1 is a linear C3 to C50 alkylene group derived from diglycidyl ether, glycerol diglycidyl ether, diglycerol diglycidyl ether, diethylene glycol diglycidyl ether, or ethylene glycol diglycidyl ether having 3 to 10 (ethylene oxide) repeating units, and

[1017] m is 1 to 10, preferably 1, 2, 3, 4 or 5.

[1018] More preferably, X = O and,

[1019] R 6 is selected from hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, hexadecenylene, heptadecylene, octadecylene, nonadecylene, and eicosylene, and

[1020] If present, R 7 is selected from hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl hexadecenyl, heptadecyl, octadecyl, nonadecyl, and eicosyl, and

[1021] R 1 is an unsubstituted C1-C8 alkylene group that does not contain a functional group, or R 1 is a linear C3 to C50 alkylene group derived from diglycidyl ether, glycerol diglycidyl ether, diglycerol diglycidyl ether, diethylene glycol diglycidyl ether, or ethylene glycol diglycidyl ether having 3 to 10 (ethylene oxide) repeating units, and

[1022] m is 1, 2, 3, 4, or 5.

[1023] Most preferably in this embodiment,

[1024] X = O and,

[1025] R 6 It is derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or resquerolic acid, and

[1026] If present, R 7 It is derived from oleic acid, ricinoleic acid, or stearic acid, and

[1027] R 1 is an unsubstituted C1-C8 alkylene group that does not contain a functional group, or R 1is a linear C3 to C50 alkylene group derived from diglycidyl ether, glycerol diglycidyl ether, diglycerol diglycidyl ether, and diethylene glycol diglycidyl ether, and

[1028] m is 1, 2, 3, 4, or 5.

[1029] Additionally, the present invention relates to the use of a fatty acid polymer compound of the above-described formula (I) in cosmetic formulations for skin and hair care, particularly conditioners and shampoos, abrasives for hard surface treatment and coating, and formulations for automobiles and other hard surface drying. For example, it is used as a separate softener for use after washing fabrics with a nonionic or anionic / nonionic detergent formulation to finish fabrics and fabric fibers after automatic washing, as a softener in fabric washing formulations based on nonionic or anionic / nonionic surfactants, and as a means to prevent or remove wrinkles in fabrics.

[1030] Additionally, the present invention relates to the use of a cosmetic composition for fiber treatment of the aforementioned fatty acid polymer compound. The fiber is preferably an amino acid-based fiber, more preferably human hair, and is particularly useful for hair strengthening, hair color maintenance, hair gloss enhancement, hair color enhancement, hair color protection, hair formation, particularly hair curling and straightening, hair conditioning, hair smoothing or softening, hair care improvement, particularly hair combability, anti-frizzyness, and anti-static properties.

[1031] A preferred composition according to the present invention is a cosmetic composition for hair treatment selected from the group consisting of hair shampoo compositions, hair care compositions, hair conditioning compositions, hair strengthening compositions, hair coloring or dyeing compositions, hair combability improvement compositions, anti-frizzy compositions, and hair rinse-off and leave-on compositions.

[1032] Additionally, the present invention relates to a composition containing at least one fatty acid polymer compound together with at least one additional component commonly used in such compositions.

[1033] Below, a number of typical examples of this type of composition in which the fatty acid polymer compound of the present invention can be advantageously used are provided.

[1034] Typical adjuvants in this type of composition are, for example, 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 7 th It was published in Ed. 1997 by JA Wenninger, GN McEwen Vol. 1-4 by The Cosmetic, Toiletry and Fragrance Association Washington DC.

[1035] In particular, the present invention relates to a hair treatment composition selected from the group consisting of hair shampoo compositions, hair conditioning compositions, hair strengthening compositions, hair coloring or dyeing compositions, hair combability improving compositions, frizz prevention compositions, and hair rinse-off and leave-on compositions as defined above. In subsequent formulations, the term “fatty acid polymer compound of the present invention” is used to refer to a compound as defined above.

[1036] Formulation Examples:

[1037] Anionic shampoo

[1038] This formulation example is intended as a basic formulation. Anionic shampoos conventionally include, but are not limited to, the following ingredients.

[1039] 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, paraffin sulfonates, sulfosuccinates, N-acyltaurids, sulfate-glycerides, sulfated alkanolamides, carboxylate salts, N-acyl-amino acid salts, silicon, etc.

[1040]

[1041] Non-ionic shampoo

[1042] This formulation example is intended as a basic formulation. Nonionic shampoos conventionally contain, but are not limited to, the following ingredients.

[1043] Monoalkanolamide, monoethanolamide, monoisopropanolamide, polyhydroxy derivatives, sucrose monolaurate, polyglycerin ether, amine oxide, polyethoxylated derivatives, sorbitol derivatives, silicone, etc.

[1044]

[1045] Ambidextrous shampoo

[1046] This formulation example is intended as the basic formulation. Formulations in this category conventionally include, but are not limited to, the following ingredients.

[1047] N-alkyl-iminodipropionate, N-alkyl-iminopropionate, amino acids, amino acid derivatives, amidobetaine, imidazolinium derivatives, sulfobetaine, sultane, betaine, silicon, etc.

[1048]

[1049] cationic shampoo

[1050] This formulation example is intended only as a basic formulation. Formulations in this category conventionally include, but are not limited to, the following ingredients.

[1051] Bis-quaternary ammonium compounds, bis-(trialkylammonium acetyl)diamine, amidoamine, ammonium alkyl ester, silicon, etc.

[1052]

[1053] Setting Agents

[1054] This formulation example is intended only as a basic formulation. Formulations in this category conventionally include, but are not limited to, the following ingredients.

[1055] Fatty acid, fatty acid ester, ethoxylated fatty acid, ethoxylated fatty acid ester, fatty alcohol, ethoxylated fatty alcohol, glycol, glycol ester, glycerin, glycerin ester, lanolin, lanolin derivative, mineral oil, petroleum jelly, lecithin, lecithin derivative, wax, wax derivative, cationic polymer, protein, protein derivative, amino acid, amino acid derivative, humectant, thickener, silicone, etc.

[1056]

[1057] "Clear Rinse-Off" Setting Agent

[1058] This formulation example is intended as a basic formulation. Formulations in this category conventionally include, but are not limited to, the following ingredients.

[1059] Fatty acid, fatty acid ester, ethoxylated fatty acid, ethoxylated fatty acid ester, fatty alcohol, ethoxylated fatty alcohol, glycol, glycol ester, glycerin, glycerin ester, lanolin, lanolin derivative, mineral oil, petroleum jelly, lecithin, lecithin derivative, wax, wax derivative, cationic polymer, protein, protein derivative, amino acid, amino acid derivative, humectant, thickener, silicone, etc.

[1060]

[1061] Hair foam setting agent

[1062] This formulation example is intended as a basic formulation. Formulations in this category conventionally include, but are not limited to, the following ingredients.

[1063] Fatty acids, fatty acid esters, ethoxylated fatty acids, ethoxylated fatty acid esters, fatty alcohols, ethoxylated fatty alcohols, glycols, glycol esters, glycerin, glycerin esters, lanolin, lanolin derivatives, mineral oil, petroleum jelly, lecithin, lecithin derivatives, waxes, wax derivatives, cationic polymers, proteins, protein derivatives, amino acids, amino acid derivatives, wetting agents, thickeners, silicones, solvents, ethanol, isopropanol, isoparaffin solvents, butane, propane, isobutane, fluorinated aerosol propellants of CFCs, dimethyl ether, compressed gases, etc.

[1064]

[1065] Hair pump spray (setting agent)

[1066] This formulation example is intended only as a basic formulation. Formulations in this category conventionally include, but are not limited to, the following ingredients.

[1067] Fatty acid, fatty acid ester, ethoxylated fatty acid, ethoxylated fatty acid ester, fatty alcohol, ethoxylated fatty alcohol, glycol, glycol ester, glycerin, glycerin ester, lanolin, lanolin derivative, mineral oil, petroleum jelly, lecithin, lecithin derivative, wax, wax derivative, cationic polymer, protein, protein derivative, amino acid, amino acid derivative, wetting agent, thickener, silicone, solvent, ethanol, isopropanol, isoparaffin solvent, etc.

[1068]

[1069] Hair setting spray

[1070] This formulation example is intended as a basic formulation. Formulations in this category conventionally include, but are not limited to, the following ingredients.

[1071] Fatty acids, fatty acid esters, ethoxylated fatty acids, ethoxylated fatty acid esters, fatty alcohols, ethoxylated fatty alcohols, glycols, glycol esters, glycerins, glycerin esters, lanolin, lanolin derivatives, mineral oil petroleum jelly, lecithin, lecithin derivatives, waxes, wax derivatives, cationic polymers, proteins, protein derivatives, amino acids, amino acid derivatives, wetting agents, thickeners, silicones, solvents, ethanol, isopropanol, isoparaffin solvents, butane, propane, isobutane, fluorinated aerosol propellants of CFCs, dimethyl ether, compressed gases, etc.

[1072]

[1073] Hair gel setting agent

[1074] This formulation example is intended as a basic formulation. Formulations in this category conventionally include, but are not limited to, the following ingredients.

[1075] Thickeners, cellulose derivatives, acrylic acid derivatives, fixed polymers, conditioning chemicals, glycols, glycol esters, glycerin, glycerin esters, lanolin, lanolin derivatives, mineral oil, petroleum jelly, lecithin, lecithin derivatives, waxes, wax derivatives, cationic polymers, proteins, protein derivatives, amino acids, amino acid derivatives, humectants, silicones, solvents, ethanol, isopropanol, isoparaffin solvents, etc.

[1076]

[1077] Rinse-off conditioner

[1078] This formulation example is intended as a basic formulation. Formulations in this category conventionally include, but are not limited to, the following ingredients.

[1079] Hydrocarbon-based cationic conditioning agents, silicone-based cationic conditioning agents, high-melting-point fatty compounds, low-melting-point oils such as ester compounds, thickeners, cellulose derivatives, immobilized polymers, ethylene glycol, propylene glycol, glycol esters, glycerin, glycerin esters, monohydric alcohols, polyhydric alcohols, cationic polymers, nonionic and betaine co-emulsifiers, silicones, complexing agents, solvents, fragrances, vitamins, solvents, etc.

[1080]

[1081] Hair styling gel

[1082] This formulation example is intended as a basic formulation. Formulations in this category conventionally include, but are not limited to, the following ingredients.

[1083] Fixed polymers, lacquers, acrylic acid derivatives, cellulose derivatives, vinyl derivatives, conditioning chemicals, glycols, glycol esters, glycerin, glycerin esters, lanolin, lanolin derivatives, mineral oil, petroleum jelly, 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.

[1084]

[1085] Hair styling spray

[1086] This formulation example is intended as a basic formulation. Formulations in this category conventionally include, but are not limited to, the following ingredients.

[1087] Fixed polymers, lacquers, vinyl derivatives, fatty acids, fatty acid esters, ethoxylated fatty acids, ethoxylated fatty acid esters, fatty alcohols, ethoxylated fatty alcohols, glycols, glycol esters, glycerins, glycerin esters, lanolin, lanolin derivatives, mineral oil, petroleum jelly, 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, fluorinated aerosol propellants of CFCs, dimethyl ether, compressed gases, etc.

[1088]

[1089] Hair pump spray (styling)

[1090] This formulation example is intended as a basic formulation. Formulations in this category conventionally include, but are not limited to, the following ingredients.

[1091] Vinyl derivatives, fixed polymers, lacquers, fatty acids, fatty acid esters, ethoxylated fatty acids, ethoxylated fatty acid esters, fatty alcohols, ethoxylated fatty alcohols, glycols, glycol esters, glycerin, glycerin esters, lanolin, lanolin derivatives, mineral oil, petroleum jelly, 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, fluorinated aerosol propellants of CFCs, dimethyl ether, compressed gases, etc.

[1092]

[1093] The use of the fatty acid polymer derivative specified in the present invention for applications in the field of hair care yields good results in terms of strengthening, shine, hold, body, volume, moisture control, color retention, protection against environmental factors (UV, salt water, etc.), manageability, combability, frizz prevention, antistatic properties, dyeability, etc.

[1094] Additional formulation examples:

[1095] In the following formulation examples, all values ​​are expressed as "weight% of the total composition" unless otherwise noted.

[1096] Naturally Derived Crystal Clear, Betaine-Free Conditioning: Shampoo

[1097]

[1098] procedure

[1099] Polyquta 400 KC was added to a vortex of water and mixed until completely dispersed and transparent. Phase A was heated to 40 to 45°C. Pureact WS Conc, Pureact Gluco L, and Pureact MS-CG were heated to 40 to 45°C and the product was mixed and homogenized before being added to the main container. Sequentially, the components of Phase B were added and mixed until uniform and transparent. Slowly, Surfac SB09 and the fatty acid polymer compound of the present invention (Phase C) were added to the main container and mixed until uniform. The container was cooled to below 40°C, then a preservative was added and the mixture was mixed until transparent and uniform. A flavoring was added and mixed until completely emulsified and transparent. If necessary, the pH was adjusted to 4.2 to 4.7 using a citric acid solution (50% w / w). A small amount of sodium chloride (0.2% w / w) was added as needed until the desired viscosity was obtained.

[1100] Fatal Attraction Hair Mist

[1101] procedure

[1102]

[1103] procedure

[1104] Phase A was added to the container while stirring gently. It was mixed until clear. Phase B was added to Phase A while stirring at room temperature. This was mixed until homogeneous. Phase C was slowly added to Phases A and B using a fitting mixer while continuing to stir. When the mixture was homogeneous, the pH value was adjusted to 5.00–5.50 using Phase D.

[1105] Have a Peach Day Jelly Shampoo

[1106]

[1107] procedure

[1108] In the main vessel, component A of phase A was combined with shear mixing in the formula order and heated to 140°F to 149°F (60-65°C). Phase B was added to phase A in the formula order with continuous mixing. The solution was concentrated once neutralized to the desired pH. In a separate vessel, component C of phase C was combined and heated to 140°F to 149°F (60-65°C). Once homogeneous, phase C was added to phase AB under propeller mixing. Phase D was combined in a separate vessel and then added to the main vessel under continuous mixing. The mixture was transferred to the final vessel.

[1109] PEG-Free Shampoo

[1110]

[1111] procedure

[1112] The components of Phase A were heated to 70°C and mixed with moderate propeller stirring until homogeneous. Phase B was added to Phase A and mixed until homogeneous. The deionized water of Phase C was heated to 65-70°C and Quatrisoft Polymer LM-200 was dissolved. Once Quatrisoft Polymer LM-200 was completely dissolved, Tauranol I-78 was slowly added. Phase C was slowly added to Phase AB. Mixed until homogeneous and cooled to 50°C. Phase D was added in the order listed in Phases A, B, and C while stirring with a propeller at moderate speed. The mixture was cooled to room temperature.

[1113] Repairing Shampoo Bar

[1114]

[1115] procedure

[1116] Ingredients of Phase A were added to the main container while being gently mixed, and heated to 70-75°C. Phase B was added to Phase A while continuing to mix and maintaining the temperature at 70-75°C. Phase C was added to Phase AB while continuing to mix and maintaining the temperature at 70-75°C. When the batch was uniform, it was cooled, and Phase D was added to the batch. When the batch cooled to 45°C, preheated sticks were filled. Before first use, the sticks were placed in the freezer for 12-24 hours.

[1117] Frozen Yogurt Hair Mask

[1118]

[1119] procedure

[1120] Phase A was weighed in a main beaker and heated to 75°C. Phase B was sprinkled into the aqueous phase, and the process was waited until the Carbopol was completely hydrated. This was homogenized, Phase C was added to neutralize it, and it was homogenized again. Phase D was weighed in an auxiliary vessel and heated to 75°C. D was slowly added to the aqueous phase under high stirring. Then, the emulsion was cooled with moderate stirring. Phases E and F were added at 35°C and homogenized.

[1121] Crystal Clear Healthy Hair Shampoo

[1122]

[1123] procedure

[1124] Water was added to a suitable container. Hostapon SCI, Glucotain Plus, and Amphosol CS-50 were added while the water was heated to 80–85°C. The mixture was mixed at 80–85°C until homogeneous and then removed. In a separate beaker, Celquat 240C, Glucquat 125, and deionized water were mixed until homogeneous. Once homogenized, the Celquat / Gluquat Blend was added to the main batch (Phase A). The components of Phase C were added one by one and mixed thoroughly. The pH of the solution was adjusted to 6.0 to 6.5 using 20% ​​citric acid or 20% NaOH. The batch was filled to 100% with deionized water.

[1125] Hair Repairing Serum

[1126]

[1127] procedure:

[1128] The components of Phase A were added separately to a separate container while heating to 50°C and mixing. Mixing continued until uniform and homogeneous. The mixture was cooled to a temperature < 35°C. The components of Phase B and Phase C were added separately to separate containers while mixing and mixed until uniform. When the main container cooled to 35°C, Phases B and C were added to Phase A. Mixing continued until uniform. Phase D was added to the main container to adjust the pH to 4.80–5.40. Phase E was added to the main container while gently stirring and mixed until uniform.

[1129] Hair repairing serum with Keratrix

[1130]

[1131] procedure

[1132] In a separate container, the components of Phase A were added separately while heating to 50°C and mixing. This was mixed until uniform and homogeneous, and the mixture was cooled to a temperature < 35°C. In separate containers, the components of Phase B and Phase C were added separately while mixing and mixed until homogeneous. When the main container cooled to 35°C, Phases B and C were added to Phase A and mixed until homogeneous. Phase D was added to the main container to adjust the pH to 4.80–5.40. Phase E was added to the main container while gently stirring and mixed until homogeneous.

[1133] Foot More Life in Your Hair Clay Mask

[1134]

[1135] procedure:

[1136] Component A of Phase A was added in the formula order to a main vessel with propeller mixing and heated to 60-70°C. In a separate vessel, Component B of Phase B was added in the formula order under propeller mixing and heated to 60-70°C. Once Phase A and Phase B were completely homogeneous, Phase B was added to Phase A while continuously mixing. Heating was stopped when completely dispersed. Once the temperature reached 35-40°C, Phase C was added to Phase AB with continuous mixing. Phase D was added to Phases ABC, mixing was stopped, and the system was switched to a homogenizer. The mixture was homogenized for 10-30 seconds. Upon completion, the mixture was transferred to a storage vessel.

[1137] Detox Hair Sleeping Pack

[1138]

[1139] procedure

[1140] The components of Phase A were added separately to the main container while gently mixing until the mixture became homogeneous. Phase B was dispersed in the container by high-shear mixing. When the batch was homogeneous, the components of Phase C were added individually and mixed until homogeneous before the next addition. The pH was adjusted to 5.40–6.00 with sodium hydroxide and mixed until the gel became homogeneous.

[1141] Clean Beauty Light & Clean Conditioner

[1142]

[1143] procedure

[1144] Phase A was heated to 75°C while stirring. In a separate container, the components of Phase B were heated to 75°C while stirring. Phase B was added to Phase A, and mixing was continued for 10 minutes. Heat was removed, and stirring was continued until the product reached 40°C. The components of Phase C were added and mixed well under medium stirring. Phase C was added to Phases A and B at 40°C, and stirring was continued until the product reached room temperature.

[1145] Gently Bubble It Mild Shampoo

[1146]

[1147] procedure

[1148] Water was filled into a mixing container, polyquaternium-10 (B) was sprinkled into the water, and the mixture was stirred until clear. Iselux Ultra Mild (C) was poured into the main container while mixing appropriately. The phase (D) was mixed into the batch. After mixing until clear, the desired fragrance and preservative were added, and the pH was adjusted using citric acid (50% w / w solution) (G).

[1149] Coconut Dream Conditioner

[1150]

[1151] procedure

[1152] The components of Phase A were mixed and heated to 80°C. The components of Phase B were blended at 80°C. Phase B was added to Phase A. This was cooled to 40°C and Phase C was added. This was further cooled and Phase D was added, and the mixture pH was adjusted to 4.3–4.7.

[1153] Glycolic acid shampoo

[1154]

[1155] procedure

[1156] Phase A was added to the main container and mixed until homogeneous. Phase B was added to Phase A. Phase C was combined in the side container and then slowly added to Phase AB, where the pH must be >4. Preservatives were added to Phases A, B, and D. Mixing continued while the batch was initially discontinuous. Surfactants were slowly added to Phases A, B, and D until the batch became homogeneous and the viscosity increased. Finally, flavoring was added.

[1157] 2-Step Super Hydration Hair Treatment

[1158]

[1159] procedure

[1160] The components of Phase B were mixed and added to Phase A while mixing. Next, the components of Phase C were added to Phase AB. The components of Phase D were mixed and added to Phases ABC with high shear. Then, Phase E was added.

[1161] Cleansing & Nourishing Oil Shampoo

[1162]

[1163] procedure

[1164] Phase A was heated to 75-80°C. Phase B was pre-mixed and added to Part A by medium-speed mixing. This was cooled to 40°C and Phase C was added. The pH was checked and adjusted using a citric acid solution if necessary.

[1165] Hair wax formulation

[1166]

[1167] procedure

[1168] Phase A was prepared and heated to 75-80°C. Phase B was prepared and heated to 70-75°C. Phase B was added to Phase A and homogenized for a few minutes using a suitable dispersion device (e.g., Silverson, Ultra Turrax, etc.). This was cooled to 40°C and Phase B. C and D were added and mixed for a few minutes. The mixture was cooled to room temperature.

[1169] On the Go Hair Sherbet

[1170]

[1171] procedure

[1172] Phase A was added to a container while heating to 45-50°C and stirring gently. It was mixed until homogeneous. Phase B was added to Phase A while stirring. This was mixed until homogeneous. Phase C was added to Phases A and B while continuing to stir. When homogeneous, Phase D was added to Phases A, B, and C individually while stirring gently. Mixing was performed between each addition.

[1173] Dreamy Curl 24-Hr Weightless Foam

[1174]

[1175] procedure:

[1176] Water was added to the main container and mixed with propeller stirring. Styleze ES-1 was added to the vortex and dispersed. Citric acid was added and mixed for approximately 10-15 minutes. Benecel E4M was added and mixed until no particles were visible. The fatty acid polymer compound of the present invention, Amphosol CA, glycerin, and Optiphen BSB-W were added one by one and mixed until homogeneous.

[1177] Sea Salt 2-in-1 Scalp Treatment Shampoo

[1178]

[1179] procedure

[1180] Polyquaternium-10 was slowly added to water. Next, glycerin was added to the main container and mixed until completely dispersed and clear. Sequentially, component (B) was added, heated to 65-70°C, and mixed until homogeneous. Component (C) was added, the temperature was maintained at 65-70°C, and mixed until homogeneous. The pH was adjusted to 5.5-6.0 using citric acid (50% w / w solution). Component (E) was added and mixed until homogeneous. Phase (F) was added while maintaining the temperature at ~65°C and mixed until a structure was obtained. Heating was stopped, the mixture was cooled to 30°C, and component (G) was added while mixing.

[1181] Humidity-reducing sparkling hair serum

[1182]

[1183] procedure:

[1184] In the main container, the components of Phase A were added separately while gently mixing until the mixture became uniform and transparent. The remaining phases were added individually and mixed until uniform before the next addition.

[1185] D5 Pre-Primer with Argan Oil

[1186]

[1187] procedure

[1188] The components of Phase B were added to Phase A and mixed with low to medium shear force.

[1189] The components of Phase C were blended and added to Phase AB.

[1190] Example:

[1191] (Percentages represent weight % unless otherwise indicated).

[1192] As used herein, the term "castor oil" generally refers to ricinoleic acid triglycerides).

[1193] Description of nomenclature for estolide moiety and estolide compounds in this specification

[1194] In the nomenclature representing the structure of the estolide group used in the following examples, the estolide moiety refers to a compound formally obtained by at least esterification, and the carboxylic acid from which the estolide moiety is formally derived is provided in parentheses in a sequential manner. Where there are multiple subunits derived from the same acid in succession in the estolide moiety and they are indicated in parentheses, the subscript integer indicates the number of repeating units, and the carboxylic acid is indicated in parentheses.

[1195] When there are several subunits derived from the same acid in succession in the estolide portion and they are indicated in parentheses, the subscript integer indicates the number of repeating units, and the carboxylic acid is indicated in parentheses.

[1196] It should be noted that the specific carboxylic acids within parentheses or brackets are not combined in any arbitrary structure, but have the exact order of hydroxyl-carboxylic acid-derived residues and carboxylic acid-derived residues, respectively, as indicated in the terms used. Here, the last carboxylic acid given within the parentheses or brackets, respectively, is the terminal carboxylic acid of the estolide moiety. The parentheses or brackets are indicated in the exact order of the carboxylic acid residues connected by ester groups from the beginning to the end of the term and the number of residues included.

[1197] For example, the term "(12-hydroxy stearic acid - ricinoleic acid - oleic acid)" formally represents an estolide moiety in which a 12-hydroxy stearic acid molecule is connected to the carboxylic acid group of a ricinoleic acid molecule by forming an ester group through an OH group. The hydroxyl group of the ricinoleic acid molecule is connected 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 the terminal group of this specific estolide moiety; however, if the estolide moiety is a substituent of a higher-level structure (i.e., a more complex molecule), the estolide moiety is generally connected to the overall structure through the connection to the carboxylic acid group of the first mentioned residue in the term used for the estolide moiety. In this case, this is the first mentioned 12-hydroxy stearic acid residue, and the oleic acid residue is the terminal group of the estolide moiety.

[1198] Therefore, when the term used refers to a carboxylic acid chloride of the estolide structure, the acyl chloride group must be formed from the carboxylic acid group of the carboxylic acid residue mentioned first in parentheses, that is, the carboxylic acid group furthest from the terminal group.

[1199] When terms such as "dimer" or "trimer" are used, they indicate the number of carboxylic acid-derived subunits of the estolide moiety.

[1200] In the same way, the term "[(ricinoleic)2-oleic] estolide" formally refers to an estolide moiety or compound in which a ricinoleic acid molecule or residue is connected to the carboxylic acid group of an additional ricinoleic acid molecule by forming an ester group through an OH group. The hydroxyl group of the aforementioned latter ricinoleic acid residue is connected to the oleic acid molecule by forming an ester group with the carboxylic acid group of the oleic acid molecule. Oleic acid is considered the terminal group of this particular estolide moiety; however, if the estolide moiety is a substituent of a higher-level structure (i.e., a more complex molecule), the estolide moiety is connected to the overall structure through a connection to the carboxylic acid group of the first mentioned ricinoleic acid residue, and the oleic acid residue is the terminal group of the estolide moiety.

[1201] When the estolide moiety is connected by linkers via ester or amide groups, for example, the succinic acid derivative residue of [(ricinoleic acid)6-succinic acid - (ricinoleic acid)6] is connected to two ricinoleic acid estolide groups by ester groups on both sides, this is indicated by incorporating the name of the parent compound into the term applied to the entire estolide structure. Thus, a comprehensive term is provided to indicate the sequence of carboxylic acid residues.

[1202] The precise structure of the estolide is clarified primarily by its structural formula, which is thoroughly provided for the example compounds, and the structure of the example compounds can also be clearly derived by a skilled technician from the provided detailed experimental procedure.

[1203] The term “commercial polyglycerol-polyricinoleate” refers to Palsgaard® PGPR 4150, a commercially available polyglycerin-polyricinoleate produced by Palsgaard A / S, and is designated as follows.

[1204] Polyglycerol-polyricinoleate (E476) exists as a yellow, viscous liquid. Viscosity-reducing power: 74-87; max. acid number: 3 mg KOH / g; hydroxyl number: 80-100 mg KOH / g; refractive index at 65°C: 1.4630-1.4665; iodine number: 72-103 g I2 / 100g; saponification value: 170-210 mg KOH / g; polyglycerol composition: di-, tri-, and tetraglycerin, at least: 75%; polyglycerol equal to or longer than heptaglycerol, max: 10%.

[1205] Synthesis Example 1

[1206] Synthesis of (Ricinoleic-Oleic Acid) Estolide Dimer

[1207] 225 g (0.75 mol) ricinoleic acid was placed in a 1000 ml four-necked bottle equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas vent tube at room temperature under a nitrogen atmosphere. During stirring, 226.85 g (0.75 mol) oleic acid chloride was slowly added over 1.5 hours. The temperature was between 22 and 32 o It increased to C. The rise in temperature was accompanied by the formation of bubbles indicating the formation of HCl. After maintaining the temperature at 32°C for 2 more hours, it was raised to 50°C and maintained for 1 hour. Volatile substances were reduced pressure (40 o It was removed under C / 2h / 20mmHg. The conversion of OH groups was determined by 1H NMR spectroscopy. The conversion rate of OH groups was 100%.

[1208] A brown, transparent oil having the structure below was obtained:

[1209]

[1210] Synthesis Example 2

[1211] [(Ricinoleic acid) 2 Synthesis of -Oleic Acid] Estolide Trimer

[1212] 34.87 g (0.293 mol) SOCl2 was placed in a 250 ml four-necked bottle equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas discharge tube at room temperature under a nitrogen atmosphere. While stirring, 110 g (0.195 mol) of the estolide dimer of Synthesis Example 1 was slowly added over 1 hour. After the addition was finished, the temperature was raised to 80°C. The temperature was maintained at 80°C for 1 hour. Volatile substances were removed under reduced pressure (80°C / 2h / 20 mmHg). The vacuum was broken using nitrogen, and 57.75 g (0.195 mol) of ricinoleic acid was added to the carboxylic acid chloride intermediate over 45 minutes at 80°C. The temperature was maintained for 2 hours. Volatile substances were removed under reduced pressure (40°C / 2h / 20 mmHg). The conversion of the OH group was determined by 1H NMR spectroscopy. The conversion rate of the OH group was 100%.

[1213] A brown, transparent oil having the structure below was obtained:

[1214]

[1215] Synthesis Example 2a

[1216] [(Ricinoleic acid) 2 Synthesis of Stearic Acid Estolide Trimer

[1217] Two 250ml three-necked bottles A and B, equipped with a reflux condenser, thermometer and magnetic stirrer, dropping funnel and gas discharge tube, were flushed with nitrogen.

[1218] Fatty acid chloride was reacted with ricinoleic acid using bottle A to produce chain-extended fatty acid ester acids. Subsequently, SOCl2 was added to obtain the corresponding fatty acid ester acid chloride.

[1219] The fatty acid ester acid chloride formed using bottle B was reacted with ricinoleic acid to produce a chain-extended fatty acid ester acid. Subsequently, SOCl2 was added to obtain the corresponding fatty acid ester acid chloride. This fatty acid chloride was transferred back to bottle A and reacted with fresh ricinoleic acid. The aforementioned cycle can be repeated until a hexamer estolide [(ricinoleic acid)5-stearic acid] is prepared.

[1220] General procedure for the synthesis of chain-elongated fatty acids:

[1221] The calculated amount of ricinoleic acid was placed in a bottle. An equimolar amount of fatty acid ester acid chloride was slowly added at room temperature. To complete the reaction, the temperature was raised to 80 o It was increased to C for 3 hours. The complete conversion of the OH group is 1 It was determined by H NMR spectroscopy.

[1222] General procedure for the synthesis of fatty acid ester acid chlorides:

[1223] The calculated amount of fatty acids was placed in a bottle. SOCl2 (3 molar excess) was slowly added at room temperature. Then, the mixture was heated to 80°C. The temperature was maintained for 3 hours. Afterward, the excess SOCl2 was added under reduced pressure (80 o It was removed under C / 2h / 20mmHg. The complete conversion of the C(O)OH group to the C(O)Cl group is 1 It was determined by H NMR spectroscopy.

[1224] The table below summarizes the materials and quantities used.

[1225]

[1226] Note: The term "Ricy" replaces the term "ricinoleic acid" which denotes the ricinoleyl radical.

[1227] The chemical formula of [(Ricin)2-stearic acid] is as follows.

[1228]

[1229] Synthesis Example 2b

[1230] Synthesis of (Ricinoleic acid-12-hydroxystearic acid-oleic acid) Estolide Trimer

[1231] The aforementioned procedure was repeated for Synthesis Example 2a.

[1232] The table below summarizes the materials and quantities used.

[1233]

[1234] Note: The term "Ricy" replaces the term "Ricinoleic acid" representing the ricinoleyl radical, and the term "12-hydroxy-stea" replaces the term "12-hydroxy stearic acid" representing the 12-hydroxy stearyl radical.

[1235] The chemical formula of ricin-(12-hydroxystea)-oleic acid is as follows.

[1236]

[1237] Synthesis Example 2c

[1238] Synthesis of (12-hydroxy stearic acid-ricinoleic acid) estolide trimer

[1239] The aforementioned procedure was repeated for Synthesis Example 2a.

[1240] The table below summarizes the materials and quantities used.

[1241]

[1242] Note: The term "Ricy" replaces the term "Ricinoleic acid" representing the ricinoleyl radical, and the term "12-hydroxy-stea" replaces the term "12-hydroxy stearic acid" representing the 12-hydroxy stearyl radical.

[1243] The chemical formula of (12-hydroxystea-ricy-oleic acid) is as follows:

[1244]

[1245] Synthesis Example 3

[1246] [(Ricinoleic acid)5 -Oleic acid] Estolide hexamer and the corresponding [(Ricinoleic acid) 5 Synthesis of Oleic Acid Chloride Hexamer

[1247] Two 100ml three-necked bottles A and B, equipped with a reflux condenser, thermometer and magnetic stirrer, dropping funnel and gas discharge tube, were flushed with nitrogen.

[1248] Fatty acid chloride was reacted with ricinoleic acid using bottle A to produce chain-extended fatty acid ester acids. Subsequently, SOCl2 was added to obtain the corresponding fatty acid ester acid chloride.

[1249] The fatty acid ester acid chloride formed using bottle B was reacted with ricinoleic acid to produce a chain-extended fatty acid ester acid. Subsequently, SOCl2 was added to obtain the corresponding fatty acid ester acid chloride. This fatty acid chloride was transferred back to bottle A and reacted with fresh ricinoleic acid. The aforementioned cycle was repeated until hexamer estolide [(ricinoleic acid) 5-oleic acid] was prepared.

[1250] General procedure for the synthesis of chain-extended fatty acid esters:

[1251] The calculated amount of ricinoleic acid was placed in a bottle. An equimolar amount of fatty acid ester acid chloride was slowly added at room temperature. To complete the reaction, the temperature was raised to 80 o It was increased to C for 3 hours. The complete conversion of the OH groups of ricinoleic acid to esters is 1 It was determined by H NMR spectroscopy.

[1252] General procedure for the synthesis of fatty acid ester chlorides:

[1253] The calculated amount of fatty acid was placed in a bottle. SOCl2 (three-fold molar excess) was slowly added at room temperature. Then, the mixture was heated to 80°C. The temperature was maintained for 3 hours. Afterward, the excess SOCl2 was removed under reduced pressure (80°C / 2h / 20mmHg). The complete conversion of the C(O)OH group to the C(O)Cl group is 1It was determined by H NMR spectroscopy.

[1254] The table below summarizes the materials and quantities used.

[1255]

[1256] Note: The term "Ricy" replaces the term "Ricinoleic acid" representing the ricinoleyl radical, and the term "12-hydroxy-stea" replaces the term "12-hydroxy stearic acid" representing the 12-hydroxy stearyl radical.

[1257] Essentially, a brown, transparent oil having [(ric)5-oleic acid] of the following structure was obtained:

[1258]

[1259] The corresponding [(ric)5-oleic acid] chloride has the following structure:

[1260]

[1261] Synthesis Example 4

[1262] Branched bis-[(ricinoleic acid) based on bis 2,2-hydroxymethylpropionic acid 2 -Oleic acid] Synthesis of estolide

[1263] 48.88 g (0.0567 mol) of the [(ricinoleic acid)2-oleic acid] chloride of Synthesis Example 3 and 3.80 g (0.0284 mol) of bis-2,2-hydroxymethylpropionic acid were mixed in a 100 ml three-necked bottle equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas vent tube. The mixture was heated to 100°C for 8 hours. Volatile substances were subjected to reduced pressure (80 o It was removed under C / 1h / 20mmHg. The complete conversion of the OH groups of 2,2-hydroxymethylpropionic acid is 1 It was determined by H NMR spectroscopy.

[1264] A brown, transparent oil having the following structure was obtained:

[1265]

[1266] R =

[1267]

[1268] Synthesis Example 4a

[1269] Dendrimer bis-[(ricinoleic acid) 2 -Oleic acid] Synthesis of estolide

[1270] 64.57 g (0.03617 mol) of the bis-2,2-hydroxymethylpropionic acid-based branched bis-[(ricinoleic acid)2-oleic acid] estolide of Synthesis Example 4 was heated to 80°C in a 100 ml three-necked bottle equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas vent tube. 8.61 g (0.0723 mol) SOCl2 was added within 10 minutes. The reaction was maintained for 4 hours. Volatile substances were removed under reduced pressure (80°C / 1 h / 20 mmHg). The complete conversion of the C(O)OH group to the C(O)Cl group is 1 Determined by ¹H NMR spectroscopy. 2.42 g (0.01808 mol) bis-2,2-hydroxymethylpropionic acid was added at 80 °C and the reaction was maintained for an additional 5 hours. Volatile substances were removed under reduced pressure (80 °C / 0.5 h / 20 mmHg). The complete conversion of the terminal OH groups of bis-2,2-hydroxymethylpropionic acid is 1 It was determined by H NMR spectroscopy.

[1271] Essentially, a viscous brown transparent oil having the following dendrimer structure was obtained:

[1272]

[1273] R =

[1274]

[1275] Synthesis Example 4b

[1276] Branched bis-[(ricinoleic acid) based on bis 2,2-hydroxymethylpropionic acid 2 -Stearic acid] Synthesis of estolide

[1277] 95.06 g (0.1124 mol) of [(ricinoleic acid)2-stearic acid] estoride of Synthesis Example 2a was placed in a 250 ml three-necked bottle equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas vent tube, 80 o It was heated to C. 33.8g (0.28mol) SOCl2 was added within 10 minutes. The reaction was maintained for 4 hours. Volatile substances were removed under reduced pressure (80 o It was removed under C / 1h / 20mmHg. The complete conversion of the C(O)OH group to the C(O)Cl group is 1 It was determined by H NMR spectroscopy.

[1278] 92.88 g (0.1075 mol) of (ricinoleic acid)2-stearic acid chloride intermediate and 7.22 g (0.0538 mol) of bis-2,2-hydroxymethylpropionic acid were mixed at 80°C in a 250 ml three-necked bottle equipped with a reflux condenser, thermometer, mechanical stirrer, dropping funnel, and gas vent tube, and the reaction was maintained for an additional 5 hours. Volatile substances were removed under reduced pressure (80 o It was removed under C / 0.5h / 20mmHg. The complete conversion of the OH groups of bis-2,2-hydroxymethylpropionic acid is 1 It was determined by H NMR spectroscopy.

[1279] A viscous, brown, transparent oil having the structure essentially below was obtained:

[1280]

[1281] R=

[1282]

[1283] Synthesis Example 4c

[1284] Synthesis of branched bis-(ricinoleic acid-12-hydroxystearic acid-oleic acid) estolide based on bis-2,2-hydroxymethylpropionic acid

[1285] 102.95 g (0.1218 mol) of the (ricinoleic acid-12-hydroxy stearic acid-oleic acid) estolide of Synthesis Example 2b was heated to 80°C in a 250 ml three-necked bottle equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas vent tube. 42.8 g (0.36 mol) SOCl2 was added within 10 minutes. The reaction was maintained for 4 hours. Volatile substances were removed under reduced pressure (80°C / 1 h / 20 mmHg). The complete conversion of the C(O)OH group to the C(O)Cl group is 1 It was determined by H NMR spectroscopy.

[1286] 104.22 g (0.1206 mol) of bis-(ricinoleic acid-12-hydroxystearic acid-oleic acid) chloride intermediate and 8.09 g (0.0603 mol) of bis-2,2-hydroxymethylpropionic acid were mixed at 80°C in a 250 ml three-necked bottle equipped with a reflux condenser, thermometer, mechanical stirrer, dropping funnel, and gas venting tube, and the reaction was maintained for an additional 5 hours. Volatile substances were removed under reduced pressure (80°C / 0.5 h / 20 mmHg). The complete conversion of OH groups from bis-2,2-hydroxymethylpropionic acid is 1 It was determined by H NMR spectroscopy.

[1287] A viscous, brown, transparent oil having essentially the following structure was obtained:

[1288]

[1289] R =

[1290]

[1291] Synthesis Example 4d

[1292] Synthesis of branched (12-hydroxystearic acid-ricinoleic acid-oleic acid) estolides based on bis-2,2-hydroxymethylpropionic acid

[1293] 98.05 g (0.116 mol) of (12-hydroxy stearic acid-ricinoleic acid-oleic acid) estolide of Synthesis Example 2c was heated to 80°C in a 250 ml three-necked bottle equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas vent tube. 30.08 g (0.25 mol) SOCl2 was added within 10 minutes. The reaction was maintained for 4 hours. Volatile substances were removed under reduced pressure (80°C / 1 h / 20 mmHg). The complete conversion of the C(O)OH group to the C(O)Cl group is 1 It was determined by H NMR spectroscopy.

[1294] 97.4 g (0.1127 mol) of (12-hydroxystearic acid-ricinoleic acid-oleic acid) chloride intermediate and 7.56 g (0.0564 mol) of bis-2,2-hydroxymethylpropionic acid were mixed at 80°C in a 250 ml three-necked bottle equipped with a reflux condenser, thermometer, mechanical stirrer, dropping funnel, and gas vent, and the reaction was maintained for an additional 5 hours. Volatile substances were removed under reduced pressure (80°C / 0.5 h / 20 mmHg). The complete conversion of the OH groups of the hydroxymethyl group 1 It was determined by H NMR spectroscopy.

[1295] A viscous, brown, transparent oil having essentially the following structure was obtained:

[1296]

[1297] R=

[1298]

[1299] Synthesis Example 5

[1300] Alpha-branched bis-[(ricinoleic acid) based on bis 2,2-hydroxymethylpropionic acid 5 -Oleic acid] Synthesis of estolide

[1301] 29.53 g (0.0173 mol) of the [(ricinoleic acid)5-oleic acid] chloride of Synthesis Example 3 and 1.16 g (0.00866 mol) of bis-2,2-hydroxymethylpropionic acid were mixed in a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, a magnetic stirrer, a dropping funnel, and a gas discharge tube. The mixture was heated to 105°C for 5 hours. Volatile substances were removed under reduced pressure (80°C / 10 min / 20 mmHg). The complete conversion of the OH groups of bis-2,2-hydroxymethylpropionic acid is 1 It was determined by H NMR spectroscopy.

[1302] A brown, transparent oil having the following structure was obtained:

[1303]

[1304] R =

[1305]

[1306] Synthesis Example 6

[1307] Synthesis of chloroacetic acid ester derivatives of glycerol-based estolides

[1308] 40 g (0.434 mol) of glycerol was placed at room temperature in a 100 ml three-necked bottle equipped with a reflux condenser, thermometer, mechanical stirrer, dropping funnel, and gas vent tube. During stirring, 49.05 g (0.434 mol) of chloroacetic acid chloride was added over a period of 45 minutes. During the addition, the temperature increased to 83°C. Subsequently, the temperature was increased to 120°C over a period of 2 hours. The formation of chloroacetic acid esters is 1 It was confirmed by H NMR spectroscopy.

[1309] 5.72 g (0.034 mol) of glycerol monochloroacetate was mixed with 39.50 g (0.068 mol) of the [(ricinoleic acid)1-oleic acid] chloride of Synthesis Example 3 at room temperature. The mixture was heated at 100°C for 8 hours. Volatile substances were removed under reduced pressure (80°C / 1 h / 20 mmHg). The complete conversion of OH groups and the formation of additional ester moiety are 1 It was confirmed by H NMR spectroscopy.

[1310] Essentially, a brown, transparent oil was obtained having the approximate structure below:

[1311]

[1312] R =

[1313]

[1314] Synthesis Example 7

[1315] Synthesis of chloroacetic acid ester derivatives of castor oil-based estolides

[1316] 40 g (0.0428 mol) of castor oil was placed at room temperature in a 100 ml three-necked bottle equipped with a reflux condenser, thermometer, mechanical stirrer, dropping funnel, and gas vent tube. During stirring, 4.84 g (0.0428 mol) of chloroacetic acid chloride was added over a period of 10 minutes. During the addition, the temperature increased to 34°C. Subsequently, the temperature was increased to 80°C over a period of 3 hours. The formation of chloroacetic acid esters is 1 It was confirmed by H NMR spectroscopy.

[1317] Synthetic Example 3 [(ricinoleic acid) 1 49.83 g (0.0856 mol) of oleic acid chloride was added. The temperature was maintained at 80°C for 8 hours. Volatile substances were removed under reduced pressure (80°C / 2h / 20 mmHg). The complete conversion of the OH groups of the castor oil molecules and the formation of additional ester moiety are 1 It was confirmed by H NMR spectroscopy.

[1318] Essentially, a brown, transparent oil was obtained having the approximate structure below:

[1319]

[1320] R1=

[1321]

[1322] R2=

[1323]

[1324] Synthesis Example 7a

[1325] Synthesis of chloroacetic acid ester derivatives of castor oil-based estolides

[1326] 80 g (0.0857 mol) of castor oil was placed in a 250 ml three-necked bottle equipped with a reflux condenser, thermometer, mechanical stirrer, dropping funnel, and gas vent tube, and heated to 60°C. During stirring, 9.68 g (0.0857 mol) of chloroacetic acid chloride was added over a period of 10 minutes. During the addition, the temperature increased to 80°C. Subsequently, the temperature was maintained at 80°C for an additional 1.5 hours. The formation of chloroacetic acid esters 1 It was confirmed by H NMR spectroscopy.

[1327] [(Ricinoleic acid) from Synthesis Example 2a 1 100 g (0.1714 mol) of [-stearic acid] chloride was added. The temperature was maintained at 80°C for 4 hours. Volatile substances were removed under reduced pressure (90°C / 2h / 20 mmHg). The complete conversion of the OH groups of the castor oil molecules and the formation of additional ester moiety are 1 It was confirmed by H NMR spectroscopy.

[1328] Essentially, a brown wax-like substance having the approximate structure below was obtained:

[1329]

[1330] R1=

[1331]

[1332] R2=

[1333]

[1334] Example 1

[1335] [(Ricinoleic acid) 2 Synthesis of the amine salt of the tertiary amino alcohol ester of -oleic acid] estolide

[1336] 300 ml of n-heptane was mixed with 49.69 g (0.0577 mol) of the [(ricinoleic acid)2-oleic acid] chloride of Synthesis Example 3 at room temperature in a 500 ml four-necked bottle equipped with a reflux condenser, thermometer, mechanical stirrer, dropping funnel, and gas vent tube. 5.95 g (0.0577 mol) of (CH3)2NCH2CH2CH2OH was added over 20 minutes. The temperature was increased to 37°C. The temperature was maintained for 30 minutes. The n-heptane was removed under reduced pressure (30°C / 2h / 20 mmHg). The conversion of the OH groups of (CH3)2NCH2CH2CH2OH and the formation of esters 1 It was confirmed by H NMR spectroscopy.

[1337] A brown wax having the following structure was obtained:

[1338]

[1339] R =

[1340]

[1341] Example 2

[1342] [(Ricinoleic acid) 5 Synthesis of the amine salt of the tertiary amino alcohol ester of -oleic acid] estolide

[1343] 40 ml of n-heptane was mixed with 49.19 g (0.0289 mol) of the (ricinoleic acid) 5-oleoyl chloride of Synthesis Example 3 at 40°C in a 250 ml four-necked bottle equipped with a reflux condenser, thermometer, mechanical stirrer, dropping funnel, and gas vent tube. 2.89 g (0.0289 mol) of (CH3)2NCH2CH2CH2OH was added over 5 minutes. The temperature was increased to 43°C. The temperature was maintained for 1 hour. The n-heptane was removed under reduced pressure (30°C / 2h / 20 mmHg). The conversion of the OH groups of (CH3)2NCH2CH2CH2OH and the formation of esters 1 It was confirmed by H NMR spectroscopy.

[1344] A brown wax having the following structure was obtained:

[1345]

[1346] R =

[1347]

[1348] Example 3

[1349] Branched bis-[(ricinoleic acid) 2 Synthesis of the amine salt of the tertiary amino alcohol ester of -oleic acid] estolide

[1350] 25 g (0.014 mol) of alpha-branched bis-[(ricinoleic acid)2-oleic acid]estolide of Synthesis Example 4 was mixed with 11 g (0.092 mol) SOCl2 at 50°C in a 100 ml three-necked bottle equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas discharge tube. The mixture was heated to 80°C for 2.5 hours. Afterward, the excess SOCl2 was removed under reduced pressure (80°C / 1 h / 20 mmHg). The formation of acid chloride is 1 It was confirmed by H NMR spectroscopy.

[1351] 22.4 g (0.0124 mol) of acid chloride was transferred to a 250 ml four-necked bottle equipped with a reflux condenser, thermometer, mechanical stirrer, and dropping funnel. 140 ml of n-heptane and 1.28 g (0.00825 mol) of (CH3)2NCH2CH2CH2OH were added over 5 minutes. The temperature was raised to 28°C and maintained for 1 hour. The n-heptane was removed under reduced pressure (30°C / 3h / 20 mmHg). The conversion of the OH groups of (CH3)2NCH2CH2CH2OH and the formation of esters 1 It was confirmed by H NMR spectroscopy.

[1352] A brown wax having the following structure was obtained:

[1353]

[1354] R =

[1355]

[1356] Example 3a

[1357] Dendrimer bis-[(ricinoleic acid) 2 Synthesis of the amine salt of the tertiary amino alcohol ester of -oleic acid] estolide

[1358] 25 g (0.014 mol) of the branched bis-[(ricinoleic acid)2-oleic acid] estolide of Synthesis Example 4a was mixed with 11 g (0.092 mol) SOCl2 at 50°C in a 100 ml three-necked bottle equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas vent tube. The mixture was heated to 80°C for 2.5 hours. Afterward, the excess SOCl2 was removed under reduced pressure (80°C / 1 h / 20 mmHg). The formation of acid chloride is 1 It was confirmed by H NMR spectroscopy.

[1359] 22.4 g (0.0124 mol) of acid chloride was transferred to a 250 ml four-necked bottle equipped with a reflux condenser, thermometer, mechanical stirrer, and dropping funnel. 140 ml of n-heptane and 1.28 g (0.00825 mol) of (CH3)2NCH2CH2CH2OH were added over 5 minutes. The temperature was raised to 28°C and maintained for 1 hour. The n-heptane was removed under reduced pressure (30°C / 3h / 20 mmHg). The conversion of OH groups of (CH3)2NCH2CH2CH2OH and the formation of esters 1 It was confirmed by H NMR spectroscopy.

[1360] A brown wax having the following structure was obtained:

[1361]

[1362] R =

[1363]

[1364] Example 3b

[1365] Alpha-branched bis-[(ricinoleic acid) 2 Synthesis of the amine salt of the tertiary amino alcohol ester of -Stearic acid]

[1366] 77 g (0.0430 mol) of alpha-branched bis-[(ricinoleic acid)2-stearic acid]estolide of Synthesis Example 4b was mixed with 34.5 g (0.29 mol) SOCl2 at 50°C in a 250 ml three-necked bottle equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas vent tube. The mixture was heated to 80°C for 2.5 hours. Afterward, the excess SOCl2 was removed under reduced pressure (80°C / 1 h / 20 mmHg). The formation of acid chloride is 1 It was confirmed by H NMR spectroscopy.

[1367] 71.5 g (0.0396 mol) of acid chloride was transferred to a 500 ml four-necked bottle equipped with a reflux condenser, thermometer, mechanical stirrer, and dropping funnel. 190 g of n-heptane and 4.09 g (0.0396 mol) of (CH3)2NCH2CH2CH2OH were added over 5 minutes. The temperature was raised to 30°C and maintained for 1 hour. The n-heptane was removed under reduced pressure (30°C / 3h / 20 mmHg). The conversion of OH groups of (CH3)2NCH2CH2CH2OH and the formation of esters 1 It was confirmed by H NMR spectroscopy.

[1368] A brown wax having the following structure was obtained:

[1369]

[1370] R =

[1371]

[1372] Example 3c

[1373] Synthesis of the amine salt of the tertiary amino alcohol ester of alpha-branched bis-(ricinoleic acid-12-hydroxy stearic acid-oleic acid) estolide

[1374] 89.4 g (0.05 mol) of alpha-branched bis-(ricinoleic acid-12-hydroxy stearic acid-oleic acid) estolide of Synthesis Example 4c was mixed with 40.4 g (0.34 mol) SOCl2 at 50°C in a 250 ml three-necked bottle equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas vent tube. The mixture was heated to 80°C for 2.5 hours. Subsequently, the excess SOCl2 was removed under reduced pressure (80°C / 1 h / 20 mmHg). The formation of acid chloride is 1 It was confirmed by H NMR spectroscopy.

[1375] 85.11 g (0.0471 mol) of the above acid chloride was transferred to a 500 ml four-necked bottle equipped with a reflux condenser, thermometer, mechanical stirrer, and dropping funnel. 187 g of n-heptane and 4.86 g (0.0471 mol) of (CH3)2NCH2CH2CH2OH were added over 5 minutes. The temperature was raised to 32°C and maintained for 1 hour. The n-heptane was removed under reduced pressure (30°C / 3h / 20 mmHg). The conversion of the OH groups of (CH3)2NCH2CH2CH2OH and the formation of esters 1 It was confirmed by H NMR spectroscopy.

[1376] A brown wax having the following structure was obtained:

[1377]

[1378] R =

[1379]

[1380] Example 3d

[1381] Synthesis of the amine salt of the tertiary amino alcohol ester of alpha-branched bis-(12-hydroxy stearic acid-ricinoleic acid) estolide

[1382] 78 g (0.0436 mol) of alpha-branched bis-(12-hydroxy stearic acid-ricinoleic acid) estolide of Synthesis Example 4d was mixed with 22.77 g (0.19 mol) SOCl2 at 50°C in a 250 ml three-necked bottle equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas vent tube. The mixture was heated to 80°C for 2.5 hours. Afterward, the excess SOCl2 was removed under reduced pressure (80°C / 1 h / 20 mmHg). The formation of acid chloride is 1 It was confirmed by H NMR spectroscopy.

[1383] 76.15 g (0.0421 mol) of acid chloride was transferred to a 500 ml four-necked bottle equipped with a reflux condenser, thermometer, mechanical stirrer, and dropping funnel. 200 g of n-heptane and 4.34 g (0.0421 mol) of (CH3)2NCH2CH2CH2OH were added over 5 minutes. The temperature was raised to 28°C and maintained for 1 hour. The n-heptane was removed under reduced pressure (30°C / 3h / 20 mmHg). The conversion of OH groups and the formation of esters are 1 It was confirmed by H NMR spectroscopy.

[1384] A brown wax having the following structure was obtained:

[1385]

[1386] R =

[1387]

[1388] Example 4

[1389] Alpha-branched bis-[(ricinoleic acid) 5 Synthesis of the amine salt of the tertiary amino alcohol ester of -oleic acid] estolide

[1390] 28.63 g (0.00825 mol) of alpha-branched bis-[(ricinoleic acid)5-oleic acid]estolide of Synthesis Example 5 was mixed with 7.2 g (0.0605 mol) SOCl2 at room temperature in a 100 ml three-necked bottle equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas vent tube. The mixture was heated to 80°C for 2.5 hours. Afterward, the excess SOCl2 was removed under reduced pressure (80°C / 1 h / 20 mmHg). The formation of the acid chloride thus formed is 1 It was confirmed by H NMR spectroscopy.

[1391] The temperature was adjusted to 45°C, and 40 ml of n-heptane and 0.85 g (0.00825 mol) of (CH3)2NCH2CH2CH2OH were added over 5 minutes. The temperature was maintained for 1 hour. The n-heptane was removed under reduced pressure (30°C / 3h / 20 mmHg). The conversion of OH groups of (CH3)2NCH2CH2CH2OH and the formation of esters 1 It was confirmed by H NMR spectroscopy.

[1392] A brown wax having the following structure was obtained:

[1393]

[1394] R =

[1395]

[1396] Example 5 (not in accordance with the present invention)

[1397] [(Ricinoleic acid) 2 Synthesis of tertiary amino alcohol esters of oleic acid estolides

[1398] The protocol described for Example 1 was repeated, except that n-heptane is not removed under reduced pressure.

[1399] Instead, the n-heptane solution was transferred to a separating funnel and mixed with a basic 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 lower 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. n-heptane was removed under reduced pressure (30°C / 2h / 20 mmHg). The formation of tertiary amino alcohol esters is 1 It was confirmed by H NMR spectroscopy.

[1400] A low-viscosity brown liquid having the following structure was obtained:

[1401]

[1402] R =

[1403]

[1404] Example 6

[1405] [(Ricinoleic acid) 2 -Oleic Acid] Synthesis of Glycerol Diglycidyl Ether-Based Quarts Using Amine Salts of Tertiary Amino Alcohol Esters of Estolides

[1406] In a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer, 1.5 g (0.01093 mol epoxy groups; specifically, epoxy content 0.00729 mol epoxy groups / 1 g) glycerol diglycidyl ether, 10.55 g (0.01093 mol) of the amine salt from Example 1, 55 g 2-propanol, and 0.14 g deionized water were mixed at room temperature. The mixture was heated to 80°C for 11 hours. Afterward, volatile substances were removed under reduced pressure (40°C / 2h / 20 mmHg). The complete conversion of the epoxy groups is 1 It was confirmed by H NMR spectroscopy.

[1407] A brown viscous oil having the following structure was obtained:

[1408]

[1409] R =

[1410]

[1411] Example 7

[1412] [(Ricinoleic acid) 2 Synthesis of Glycerol Triglycidyl Ether-Based Quarts Using Amine Salts of Tertiary Amino Alcohol Esters of Oleic Acid

[1413] In a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer, 1.5 g (0.01004 mol epoxy groups; specifically, an epoxy content of 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 hours. Afterward, volatile substances were removed under reduced pressure (40°C / 2h / 20 mmHg). The complete conversion of the epoxy groups 1 It was confirmed by H NMR spectroscopy.

[1414] A brown viscous oil having the following structure was obtained:

[1415]

[1416] R =

[1417]

[1418] Example 8

[1419] [(Ricinoleic acid) 2 Synthesis of diglycerol triglycidyl ether-based quarts using the amine salt of the tertiary amino alcohol ester of estolide [-oleic acid]

[1420] In a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer, 1.62 g (0.01004 mol epoxy groups; specifically, epoxy content 0.00621 mol epoxy groups / 1 g) diglycerol triglycidyl ether, 10.14 g (0.01004 mol) of the amine salt of 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 hours. Afterward, volatile substances were removed under reduced pressure (40°C / 2h / 20 mmHg). The complete conversion of the epoxy groups is 1 It was confirmed by H NMR spectroscopy.

[1421] A brown viscous oil having the following structure was obtained:

[1422]

[1423] R =

[1424]

[1425] Example 9

[1426] [(Ricinoleic acid) 2 Synthesis of polyglycerol polyglycidyl ether-based quarts using the amine salt of the tertiary amino alcohol ester of estolide [-oleic acid]

[1427] In a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer, 1.68 g (0.01004 mol epoxy groups, specifically epoxy content 0.00597 mol epoxy groups / 1 g) 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 hours. Afterward, volatile substances were removed under reduced pressure (40°C / 2h / 20 mmHg). The complete conversion of the epoxy groups is 1 It was confirmed by H NMR spectroscopy.

[1428] A brown, viscous oil with the following approximate structure was obtained:

[1429]

[1430] R =

[1431]

[1432] Example 10

[1433] [(Ricinoleic acid) 5 -Oleic Acid] Synthesis of Glycerol Diglycidyl Ether-Based Quarts Using Amine Salts of Tertiary Amino Alcohol Esters of Estolides

[1434] In a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer, 0.69 g (0.0045 mol epoxy groups, specifically epoxy content 0.00729 mol epoxy groups / 1 g) glycerol diglycidyl ether, 8.42 g (0.0045 mol) of the amine salt of 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 hours. Afterward, volatile substances were removed under reduced pressure (40°C / 2h / 20 mmHg). The complete conversion of the epoxy groups is 1 It was confirmed by H NMR spectroscopy.

[1435] A brown viscous oil having the following structure was obtained:

[1436]

[1437] R =

[1438]

[1439] Example 11

[1440] Alpha-branched bis-[(ricinoleic acid) 2 -Oleic Acid] Synthesis of Glycerol Diglycidyl Ether-Based Quarts Using Amine Salts of Tertiary Amino Alcohol Esters of Estolides

[1441] 0.46 g (0.0031 mol epoxy groups, specifically epoxy content 0.00729 mol epoxy groups / 1 g) glycerol diglycidyl ether, 6.0 g (0.0031 mol) of the amine salt of Example 3, 50 g of 2-propanol, and 0.1 g of deionized water were mixed at room temperature in a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer. The mixture was heated to 80°C for 11 hours. Afterward, volatile substances were removed under reduced pressure (40°C / 2h / 20 mmHg). The complete conversion of the epoxy groups is 1 It was confirmed by H NMR spectroscopy.

[1442] A brown wax with the following approximate structure was obtained:

[1443]

[1444] R =

[1445]

[1446] Example 11a

[1447] Alpha-branched bis-[(ricinoleic acid) 2 Synthesis of glycerol diglycidyl ether-based quarts using the amine salt of the tertiary amino alcohol ester of estolide [-Stearic acid]

[1448] In a 250 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer, 2.98 g (0.02417 mol epoxy groups; specifically, epoxy content 0.00729 mol epoxy groups / 1 g) 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 hours. Afterward, volatile substances were removed under reduced pressure (40°C / 2h / 20 mmHg). The complete conversion of the epoxy groups 1 It was confirmed by H NMR spectroscopy.

[1449] A brown wax having the following structure was obtained:

[1450]

[1451] R =

[1452]

[1453] Example 11b

[1454] Synthesis of glycerol diglycidyl ether-based quarts using the amine salt of the tertiary amino alcohol ester of alpha-branched bis-(ricinoleic acid-12-hydroxy stearic acid-oleic acid) estolide

[1455] In a 250 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer, 3.13 g (0.0228 mol epoxy groups, specifically epoxy content 0.00729 mol epoxy groups / 1 g) glycerol diglycidyl ether, 44.1 g (0.0228 mol) of the amine salt of 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 hours. Afterward, volatile substances were removed under reduced pressure (40°C / 2h / 20 mmHg). The complete conversion of the epoxy groups is 1It was confirmed by H NMR spectroscopy.

[1456] A brown wax with the following approximate structure was obtained:

[1457]

[1458] R =

[1459]

[1460] Example 11c

[1461] Synthesis of glycerol diglycidyl ether-based quarts using the amine salt of the tertiary amino alcohol ester of alpha-branched bis-(12-hydroxy stearic acid-ricinoleic acid-oleic acid) estolide

[1462] In a 250 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer, 3.33 g (0.0243 mol epoxy groups; specifically, epoxy content 0.00729 mol epoxy groups / 1 g) glycerol diglycidyl ether, 45.6 g (0.0243 mol) of the amine salt of 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 hours. Afterward, volatile substances were removed under reduced pressure (40°C / 2h / 20 mmHg). The complete conversion of the epoxy groups is 1 It was confirmed by H NMR spectroscopy.

[1463] A brown wax with the following approximate structure was obtained:

[1464]

[1465] R =

[1466]

[1467] Example 12

[1468] Alpha-branched bis-[(ricinoleic acid) 5 -Oleic Acid] Synthesis of Glycerol Diglycidyl Ether-Based Bisquat Using Amine Salt of Tertiary Amino Alcohol Ester of Estolide

[1469] 0.286 g (0.00209 mol epoxy groups, specifically epoxy content 0.00729 mol epoxy groups / 1 g) glycerol diglycidyl ether, 7.5 g (0.00209 mol) of the amine salt of Example 4, 50 g of 2-propanol, and 0.1 g of deionized water were mixed at room temperature in a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer. The mixture was heated to 80°C for 11 hours. Afterward, volatile substances were removed under reduced pressure (40°C / 2h / 20 mmHg). The complete conversion of the epoxy groups is 1 It was confirmed by H NMR spectroscopy.

[1470] A brown wax with the following approximate structure was obtained:

[1471]

[1472] R =

[1473]

[1474] Example 13

[1475] [(Ricinoleic acid) having the same estolide counterion 2 Synthesis of glycerol diglycidyl ether-based quarts using tertiary amino alcohol esters of oleic acid estolide

[1476] In a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer, 1.0 g (0.00729 mol epoxy groups, specifically epoxy content 0.00729 mol epoxy groups / 1 g) glycerol diglycidyl ether, 6.77 g (0.00729 mol) of the tertiary amine of Example 5, 6.15 g (0.00729 mol) of [(ricinoleic acid)2-oleic acid] of 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 11 hours. Afterward, volatile substances were removed under reduced pressure (40°C / 2h / 20 mmHg). The complete conversion of the epoxy groups 1 It was confirmed by H NMR spectroscopy.

[1477] A brown, viscous oil with the following approximate structure was obtained:

[1478]

[1479] R =

[1480]

[1481] X - =

[1482]

[1483] Example 14

[1484] [(Ricinoleic acid) having the same estolide counterion 2 - Oleic Acid] Synthesis of Glycerol Triglycidyl Ether-based Ter(Quat) Using Tertiary Amino Alcohol Esters of Estolides

[1485] In a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer, 1.0 g (0.00669 mol epoxy groups; specifically, epoxy content 0.00669 mol epoxy groups / 1 g) glycerol triglycidyl ether, 6.21 g (0.00669 mol) of the tertiary amine from Example 5, 5.64 g (0.00669 mol) of the [(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 hours. Afterward, volatile substances were removed under reduced pressure (40°C / 1h / 20 mmHg). The complete conversion of the epoxy groups 1 It was confirmed by H NMR spectroscopy.

[1486] A brown viscous oil having the following structure was obtained:

[1487]

[1488] R =

[1489]

[1490] X - =

[1491]

[1492] Example 15

[1493] [(Ricinoleic acid) 2 Synthesis of diglycerol triglycidyl ether-based ter(quat) using tertiary amino alcohol esters of oleic acid

[1494] In a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer, 1.08 g (0.00669 mol epoxy groups; specifically, epoxy content 0.00621 mol epoxy groups / 1 g) diglycerol triglycidyl ether, 6.21 g (0.00669 mol) of the tertiary amine of Example 5, 5.64 g (0.00669 mol) of [(ricinoleic acid)2-oleic acid] of 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 14 hours. Afterward, volatile substances were removed under reduced pressure (40°C / 1 h / 20 mmHg). The complete conversion of the epoxy groups 1 It was confirmed by H NMR spectroscopy.

[1495] A brown viscous oil having the following structure was obtained:

[1496]

[1497] R =

[1498]

[1499] X - =

[1500]

[1501] Example 16

[1502] [(Ricinoleic acid) 2 Synthesis of polyglycerol polyglycidyl ether-based quarts using tertiary amino alcohol esters of oleic acid estolide

[1503] In a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer, 1.12 g (0.00669 mol epoxy groups; specifically, epoxy content 0.00597 mol epoxy groups / 1 g) polyglycerol polyglycidyl ether, 6.21 g (0.00669 mol) of the tertiary amine from Example 5, 5.64 g (0.00669 mol) of the [(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 hours. Afterward, volatile substances were removed under reduced pressure (40°C / 1h / 20 mmHg). The complete conversion of the epoxy groups 1 It was confirmed by H NMR spectroscopy.

[1504] A brown, viscous oil with the following approximate structure was obtained:

[1505]

[1506] R =

[1507]

[1508] X - =

[1509]

[1510] Example 17

[1511] Example 5's [(ricinoleic acid) 2 Synthesis of diethylene glycol-based quarts using tertiary amino alcohol esters of oleic acid estolide

[1512] 9.285 g (0.01 mol) of the tertiary amine of Example 5, 1.295 g (0.01 mol) of the bis-(chloroacetic acid) ester of diethylene glycol, and 40 g of 2-propanol were mixed at room temperature in a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer. The mixture was heated to 80°C for 12 hours. Afterward, volatile substances were removed under reduced pressure (40°C / 2h / 20 mmHg). The complete conversion of the CH2Cl group is 1 It was confirmed by H NMR spectroscopy.

[1513] A brown viscous wax with the following approximate structure was obtained:

[1514]

[1515] R1=

[1516]

[1517] R2= -CH2CH2OCH2CH2- .

[1518] Example 18

[1519] [(Ricinoleic acid) of Example 1 2 Synthesis of 1,4-butanediol-based quarts using the amine salt of the tertiary amino alcohol ester of oleic acid estolide

[1520] 0.6 g (0.00593 mol epoxy group) 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 in a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer. The mixture was heated to 80°C for 11 hours. Afterward, volatile substances were removed under reduced pressure (40°C / 2h / 20 mmHg). The complete conversion of the epoxy group is 1 It was confirmed by H NMR spectroscopy.

[1521] A brown oily liquid with the following approximate structure was obtained:

[1522]

[1523] R1=

[1524]

[1525] R2= -CH2CH2CH2CH2-

[1526] Example 19

[1527] [(Ricinoleic acid) 2 Synthesis of 1,4-butanediol-succinic acid ester-based quarts using the amine salt of the tertiary amino alcohol ester of oleic acid estolide

[1528] 1.2 g (0.01186 mol epoxy group) 1,4-butanediol diglycidyl ether, 0.35 g (0.00593 mol COOH) succinic acid, 55 g 2-propanol, and 0.03 g trimethylamine were mixed at room temperature in a 100 ml three-necked bottle equipped with a reflux condenser, thermometer, and mechanical stirrer (for the formation of R2). The mixture was heated to 80°C for 15 hours. The partial conversion of the epoxy group is 1 It was confirmed by H NMR spectroscopy.

[1529] Thereafter, 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 hours. Volatile substances were removed under reduced pressure (40°C / 2h / 20 mmHg). The complete conversion of the epoxy group is 1 It was confirmed by H NMR spectroscopy.

[1530] A brown, high-viscosity liquid having the following structure was obtained:

[1531]

[1532] R1=

[1533]

[1534] R2=

[1535]

[1536] Example 20

[1537] Synthesis of glycerol estolide-based diquart

[1538] In a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer, 25 g (0.0198 mol CH2Cl group) of the chloroacetic acid ester derivative of the glycerol-based estolide of Synthesis Example 6, 1.71 g (0.0099 mol) 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 hours. Volatile substances were removed under reduced pressure (40°C / 2h / 20 mmHg). The complete conversion of the CH2Cl group is 1It was confirmed by H NMR spectroscopy.

[1539] A brown oily liquid with the following approximate structure was obtained:

[1540]

[1541] R =

[1542]

[1543] Example 21

[1544] Synthesis of N-terminated castor oil estolide-based diquarts by castor oil estolide

[1545] In a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer, 25 g (0.0119 mol CH2Cl groups) of the chloroacetic acid ester derivative of the castor oil-based estolide of Synthesis Example 7, 1.03 g (0.006 mol) 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 hours. Volatile substances were removed under reduced pressure (40°C / 2h / 20 mmHg). The complete conversion of the CH2Cl groups is 1 It was confirmed by H NMR spectroscopy.

[1546] A brown oily liquid having the following structure was obtained:

[1547]

[1548] R1 (connected to 2 of the R2-containing components above) =

[1549]

[1550] R2=

[1551]

[1552] Example 22

[1553] Synthesis of N-terminated branched castor oil estolide-based quarts by castor oil estolide

[1554] 0.22 g (0.0016 mol epoxy groups, specifically epoxy content 0.00729 mol epoxy groups / 1 g) glycerol diglycidyl ether, 0.30 g (0.0016 mol NH groups) (CH3)2NCH2CH2CH2NHCH2CH2CH2N(CH3)2, and 55 g of 2-propanol were mixed at room temperature in a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer. The mixture was heated to 80°C for 8 hours. The complete conversion of the epoxy groups is 1 It was confirmed by H NMR spectroscopy.

[1555] 6.73 g (0.0032 mol CH2Cl group) of the chloroacetic acid ester derivative of the castor oil-based estolide of Synthesis Example 7 was added, and the reaction was continued at 80°C for 10 hours. Volatile substances were removed under reduced pressure (40°C / 2h / 20 mmHg).

[1556] 1 The conversion rate of the CH2Cl group measured by H NMR spectroscopy was 97%.

[1557] A brown oily liquid with the following approximate structure was obtained:

[1558]

[1559] R1=

[1560]

[1561] R2=

[1562]

[1563] Example 23

[1564] N + ,N + - Synthesis of sugar-modified castor oil estolide-based diquarts

[1565] 0.44 g (0.0032 mol epoxy groups, specifically epoxy content 0.00729 mol epoxy groups / 1 g) glycerol diglycidyl ether, 0.62 g (0.0032 mol) N-methylglucarmine, and 66 g 1,3-propanediol were mixed at room temperature in a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer. The mixture was heated to 80°C for 8.5 hours. The complete conversion of the epoxy groups is 1 It was confirmed by H NMR spectroscopy.

[1566] 6.73 g (0.0032 mol CH2Cl group) of the chloroacetic acid ester derivative of the castor oil-based estolide of Synthesis Example 7 was added, and the reaction was continued at 80°C for 13 hours.

[1567] The conversion of the CH2Cl group is 1 It was confirmed by H NMR spectroscopy.

[1568] A yellow oily liquid containing quarts having the following approximate structure was obtained:

[1569]

[1570] R1=

[1571]

[1572] R2=

[1573]

[1574] Example 24

[1575] Synthesis of castor oil estolide derivatives having mooring quart moiety

[1576] 0.44 g (0.0032 mol epoxy groups, specifically epoxy content 0.00729 mol epoxy groups / 1 g) glycerol diglycidyl ether, 0.163 g (0.0016 mol) N,N-dimethyl-1,3-propanediamine, and 55 g 2-propanol were mixed at room temperature in a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer. The mixture was heated to 80°C for 8.5 hours. The complete conversion of the epoxy groups is 1It was confirmed by H NMR spectroscopy.

[1577] 3.36 g (0.0016 mol CH2Cl groups) of the chloroacetic acid ester derivative of the castor oil-based estolide of Synthesis Example 7 was added, and the reaction was continued at 80°C for 13 hours. Volatile substances were removed under reduced pressure (40°C / 2h / 20 mmHg). The conversion of the CH2Cl groups is 1 It was confirmed by H NMR spectroscopy.

[1578] A yellow oily liquid containing quarts having the following approximate structure was obtained:

[1579]

[1580] R1=

[1581]

[1582] R2=

[1583]

[1584] In the structural formula of the compound obtained by the above procedure, the number of repeating units n is within the range of n ≤ 30.

[1585] Example 25

[1586] Synthesis of Polyglycerol-Polyricinoleate (PGPR) Quat Derivatives

[1587] 60 g of commercial polyglycerol-polyricinoleate (0.0964 mol OH groups, specifically OH content 0.00161 mol OH groups / 1 g material) was added to a 100 ml three-necked bottle equipped with a reflux condenser, thermometer, mechanical stirrer, dropping funnel, and gas vent tube at 31°C. While stirring, 8.45 g (0.0748 mol) of chloroacetic acid chloride was added over a period of 30 minutes. The temperature was increased to 39°C. The mixture was heated to 70°C and maintained for 3 hours. Subsequently, volatile substances were removed under reduced pressure (40°C / 1 h / 20 mmHg). The formation of the chloroacetic acid ester structure is 1 It was confirmed by H NMR spectroscopy.

[1588] In a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer, 27 g (0.0307 mol CH2Cl) of the above PGPR-chloroacetic acid ester 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 hours. Volatile substances were removed under reduced pressure (40°C / 2h / 20 mmHg). The conversion of the CH2Cl group is 1 It was confirmed by H NMR spectroscopy.

[1589] I obtained yellowish wax.

[1590] Example 26

[1591] Synthesis of Polyglycerol-Polyricinoleate (PGPR) Quat Derivatives

[1592] 60 g (0.0964 mol OH groups; specifically, OH content 0.00161 mol OH groups / 1 g material) of commercial polyglycerol-polyricinoleate was added to a 100 ml three-necked bottle equipped with a reflux condenser, thermometer, mechanical stirrer, dropping funnel, and gas vent tube at 24°C. While stirring, 4.83 g (0.0427 mol) of chloroacetic acid chloride was added over a period of 30 minutes. The temperature was increased to 28°C. The mixture was heated to 70°C and maintained for 3 hours. Subsequently, volatile substances were removed under reduced pressure (40°C / 1.5 h / 20 mmHg). The formation of the chloroacetic acid ester structure is 1 It was confirmed by H NMR spectroscopy.

[1593] 27 g (0.0193 mol CH2Cl) of the above PGPR-chloroacetic acid ester 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 in a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer, and heated at 80°C for 8 hours. Volatile substances were removed under reduced pressure (40°C / 1 h / 20 mmHg). The conversion of the CH2Cl group is 1 It was confirmed by H NMR spectroscopy.

[1594] I obtained brown wax.

[1595] Example 27

[1596] Synthesis of polyquats having estolide moiety attached to glycerol units

[1597] 2.71 g (0.0197 mol epoxy groups, specifically epoxy content 0.00729 mol epoxy groups / 1 g) glycerol diglycidyl ether, 1.87 g (0.0197 mol) chloroacetic acid, 0.2 g triethylamine, and 63.4 g methoxypropyl acetate were mixed at room temperature in a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer. The mixture was heated to 100°C for 8 hours. The complete conversion of the epoxy groups is 1 It was confirmed by H NMR spectroscopy.

[1598] The mixture was cooled to room temperature, and 11.48 g (0.0197 mol) of [(ricinoleic acid)1-oleic acid] chloride, used as an intermediate in Synthesis Example 3, was added over 15 minutes. The temperature was raised to 100°C and maintained for 7 hours. The conversion of the C(O)Cl group is 1 It was confirmed by H NMR spectroscopy.

[1599] 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 hours. The conversion of the CH2Cl group is 1It was confirmed by H NMR spectroscopy. Volatile substances were removed under reduced pressure (80℃ / 5h / 20mmHg).

[1600] A brown wax with the following approximate structure was obtained:

[1601]

[1602] R1=

[1603]

[1604] In the structural formula of the compound obtained by the above procedure, the number of repeating units n is within the range of n ≤ 30.

[1605] Example 28

[1606] Each N + Synthesis of a diquart having an estolide moiety attached to a glycerol unit bonded to a group

[1607] In a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer, 10.5 g (0.0765 mol epoxy groups, specifically epoxy content 0.00729 mol epoxy groups / 1 g) glycerol diglycidyl ether, 43.09 g (0.0765 mol) of the (ricinoleic acid-oleic acid) of Synthesis 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 hours. The complete conversion of the epoxy groups is 1 It was confirmed by H NMR spectroscopy.

[1608] The solvent was removed under reduced pressure (70℃ / 4h / 20mmHg). Then, 2.67g (0.0236mol) of chloroacetic acid chloride was added. The temperature was increased to 48℃. Volatile substances were removed under reduced pressure (40℃ / 1h / 20mmHg).

[1609] 2.03g (0.0118mol) N,N,N',N' tetramethyl-1,6-hexanediamine and 24.3g propylene glycol monomethyl ether were added, and the mixture was heated to 100°C for 13 hours.

[1610] Volatile substances were removed under reduced pressure (80℃ / 5h / 20mmHg). The conversion of the CH2Cl group is 1 It was confirmed by H NMR spectroscopy.

[1611] A brown wax with the following approximate structure was obtained:

[1612]

[1613] R1=

[1614]

[1615] R2=

[1616]

[1617] Synthesis Example 29a

[1618] [(Ricinoleic acid) 6 - Succinic acid - (Ricinoleic acid) 6 Synthesis of dioxidized estolide

[1619] Two 250ml three-necked bottles A and B, equipped with a reflux condenser, thermometer and magnetic stirrer, dropping funnel and gas discharge tube, were flushed with nitrogen.

[1620] Using bottle A, the starting material dicarboxylic acid chloride succinyl dichloride or fatty acid chloride was reacted with ricinoleic acid to produce chain-extended fatty acid esters. Subsequently, SOCl2 was added to obtain the corresponding fatty acid ester chlorides.

[1621] Using bottle B, the formed fatty acid ester chloride was reacted with ricinoleic acid to produce chain-extended fatty acid esters. Subsequently, SOCl2 was added to obtain the corresponding fatty acid ester chloride. This fatty acid chloride was transferred back to bottle A and reacted with fresh ricinoleic acid. The cycle described above was repeated until estolide [(ricinoleic acid)6-succinic acid-(ricinoleic acid)6] was prepared.

[1622] General procedure for the synthesis of chain-extended fatty acid esters:

[1623] The calculated amount of ricinoleic acid was placed in a bottle. An equimolar amount of fatty acid ester chloride was slowly added at room temperature. To complete the reaction, the temperature was increased to 80°C over 3 hours. The complete conversion of the OH group is 1 It was determined by H NMR spectroscopy.

[1624] General procedure for the synthesis of fatty acid ester chlorides:

[1625] The calculated amount of fatty acid was placed in a bottle. SOCl2 (three-fold molar excess) was slowly added at room temperature. Then, the mixture was heated to 80°C. The temperature was maintained for 3 hours. Afterward, the excess SOCl2 was removed under reduced pressure (80°C / 2h / 20mmHg). The complete conversion of the C(O)OH group to the C(O)Cl group is 1 It was determined by H NMR spectroscopy.

[1626] The following table summarizes the materials and quantities used.

[1627]

[1628] Note: The term "Ricy" replaces the term "Ricinoleic acid" representing the ricinoleyl radical, and the term "Succin" replaces the term "Succinic acid" representing the succinyl radical.

[1629] Essentially, a brown, transparent oil having the following structure [(Ricin)6-succinyl-(Ricin)6] was obtained:

[1630]

[1631] Example 29b

[1632] [(Ricinoleic acid) 6 - Succinic acid - (Ricinoleic acid) 6 Synthesis of tertiary amino alcohol ester-based diquarts of diacid estolides

[1633] 59.57 g (0.0171 mol) of [(ricinoleic acid)6-succinic acid-(ricinoleic acid)6] diacid estolide of Synthesis Example 29a was mixed with 15.64 g (0.131 mol) SOCl2 at 60°C in a 250 ml three-necked bottle equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, and gas vent tube. The mixture was heated to 80°C for 3.5 hours. Subsequently, the excess SOCl2 was subjected to reduced pressure (80 o It was removed under C / 1h / 20mmHg). The formation of the corresponding acid chloride 1 It was confirmed by H NMR spectroscopy.

[1634] After cooling to room temperature, 140 g of n-heptane and 3.52 (0.0342 mol) of (CH3)2NCH2CH2CH2OH were added over 5 minutes. The temperature was 24 to 31 o It increased to C and was maintained for 4 hours. n-heptane was reduced pressure (30 o It was removed under C / 3h / 20mmHg. The conversion of OH groups and the formation of esters were 1 It was confirmed by H NMR spectroscopy.

[1635] A brown wax having the following structure was obtained:

[1636]

[1637] Example 29c

[1638] [(Ricinoleic acid) 6 - Succinic acid - (Ricinoleic acid) 6 Synthesis of glycerol-based quarts using amine salts of tertiary amino alcohol esters of diacid estolides

[1639] In a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer, 0.75 g (0.00549 mol epoxy groups; specifically, epoxy content 0.00729 mol epoxy groups / 1 g) glycerol diglycidyl ether, 10.23 g (0.00275 mol) of the amine salt of Synthesis Example 29b, 50 g of 2-propanol, and 0.1 g of deionized water were mixed at room temperature. The mixture was heated for 8 hours at 80 o Heated to C. After that, the volatile substance was reduced pressure (40 o It was removed under C / 2h / 20mmHg). The complete conversion of the epoxy group is 1 It was confirmed by H NMR spectroscopy.

[1640] A brown wax with the following approximate structure was obtained:

[1641] Quoting -[AB] n - It has a structure.

[1642] A =

[1643]

[1644] B =

[1645]

[1646] Structural formula of the compound obtained by the above procedure -[AB] n - The number of repetition units n is within the range n ≤ 30.

[1647] Application test

[1648] Combing force measurement

[1649] To quantify the effect of the compound according to the present invention, combing force measurements were performed. A Miniature Tensile Tester 175 (Dia-Stron Limited) was used.

[1650] Two different types of hair (Kerling International) were selected for this measurement.

[1651]

[1652] Hair Finishing Method 1 (Buffalo Hair)

[1653] The weight of the hair bundle to be finished was measured, and the total calculated amount of activator substance (target mg activator / 1 g buffalo hair) was dissolved in 2-propanol. The amount of 2-propanol used was calculated by the following formula:

[1654] m 2-프로판올 (g) = 1.94 xm 마무리된 모발

[1655] The 2-propanol solution was evenly distributed throughout the hair bundle. The hair bundle was air-dried for 2 hours and further treated as described in the general protocol.

[1656] Hair Finishing Method 2 (Damaged Hair)

[1657] The weight of the hair bundle to be finished was measured, and the total calculated amount of activator substance (target mg activator / 1 g buffalo hair) was dissolved in 2-propanol. The amount of 2-propanol used was calculated by the following formula:

[1658] m 2-프로판올 (g) = 0.64 xm 마무리된 모발

[1659] The 2-propanol solution was evenly distributed throughout the hair bundle. The hair bundle was air-dried for 2 hours and further treated as described in the general protocol.

[1660] General protocol for the pretreatment and handling of hair bundles

[1661] Individual hair bundles (2.5 cm) were cut from each stock bundle and equilibrated in a humidity chamber at 50% relative humidity (rel. hum.) for 12 hours. Afterward, dry tear strength and wet average strength (bundles rinsed with 38°C tap water for 30 seconds) were measured against untreated bundles (baseline measurements). Three strokes were performed. The force data from the third stroke was used for calculation.

[1662] The bundles were air-dried and equilibrated in a climate chamber for an additional 15 hours. Afterward, they were finished with a 2-propanol solution as described in hair finishing methods 1 and 2, air-dried for 2 hours, and equilibrated in a climate chamber for an additional 15 hours. Finally, dry tear strength and wet average strength (bundles rinsed with 38°C tap water for 30 seconds) were determined for the finished bundles (hair completed for measurement). Three strokes were performed. The force data from the third stroke was used for calculation.

[1663] The ratio between the combing force required before finishing (measured at the baseline) and the combing force after finishing (hair after measurement) indicates the effect of the conditioning agent.

[1664] The following formula was used to calculate the relative reduction in combing force:

[1665] Combing power reduction (%) = (Power 기준선 - strength 마무리 ) x 100 / strength 기준선

[1666] Combing force measurement results

[1667] Buffalo hair

[1668]

[1669] Damaged human hair

[1670]

[1671] The data in the two tables above regarding buffalo hair and damaged human hair show that the compound according to the present invention can reduce combing force on different keratin substrates.

[1672] A comparison of data on compounds 6, 17, and 21 on buffalo hair and damaged human hair highlights the specific effects of the compounds of the present invention on human hair.

[1673] Data on compounds 11a, 11b, and 11c demonstrate that a mixed polyfatty acid sequence composed of saturated and unsaturated fatty acids is effective on human hair.

[1674] Data for compound 29c demonstrate that, in addition to monofunctional polyfatty acid moiety terminated by monofunctional fatty acids (i.e., oleic acid, stearic acid), difunctional and higher functional polyfatty acid moiety (i.e. located within the polymer chain) is effective on human hair.

[1675] Synthesis Example 30

[1676] Synthesis of Diquart using chloroacetic acid ester derivatives of castor oil-based estolides

[1677] 117.77 g (0.1262 mol) of castor oil was placed at room temperature in a 500 ml three-necked bottle equipped with a reflux condenser, thermometer, mechanical stirrer, dropping funnel, and gas vent tube. During stirring, 14.25 g (0.1262 mol) of chloroacetic acid chloride was added over a period of 10 minutes. During the addition, the temperature was 34 o It increased to C. Afterwards, the temperature was kept at 80 for 1 hour. o Increased to C. The formation of chloroacetic acid esters 1 It was confirmed by H NMR spectroscopy.

[1678] 75.93g (0.2523mol) of oleic acid chloride was added over 20 minutes. Subsequently, 80 o The temperature was maintained at C for 2 hours. Volatile substances were subjected to reduced pressure (80 o It was removed under C / 2h / 20mmHg. The complete conversion of the OH groups of the castor oil molecule and the formation of additional ester moiety are 1 It was confirmed by H NMR spectroscopy.

[1679] Essentially, a brown, transparent oil was obtained having the approximate structure below:

[1680]

[1681] R1=

[1682]

[1683] R2=

[1684]

[1685] 185 g of 2-propanol and 10.87 g (0.0631 mol) of N,N,N',N'-tetramethyl-1,6-hexanediamine were added, and the mixture was heated to 80°C for 27 hours.

[1686] The complete conversion of the CH2Cl group is 1 It was confirmed by H NMR spectroscopy.

[1687] A brown liquid containing dequart having the following structure was obtained:

[1688]

[1689] R1 (connected to 2 of the R2-containing components above) =

[1690]

[1691] R2=

[1692]

[1693] Synthesis Example 30a

[1694] Synthesis of a diquart having an oleate counterion using a chloroacetic acid ester derivative of a castor oil-based estolide

[1695] 100g of the solution of Example 30 (0.000323mol Cl) in a 500ml beaker equipped with a magnetic stirrer - / 1g solution), 9.85g of sodium oleate (0.0323mol) and 5.5g of deionized water were mixed for 1 hour.

[1696] A second mixture of the same composition was prepared.

[1697] The two mixtures were combined and volatile substances were removed (40 o C / 20mbar / 4hrs).

[1698] A brown viscous material having the following structure was obtained:

[1699]

[1700] R1 (connected to the two R2-containing ingredients above) =

[1701]

[1702] Here, the two anions of the structural formula below have counterions.

[1703]

[1704] R2=

[1705]

[1706] The formed sodium chloride precipitates during storage.

[1707] Synthesis Example 30b

[1708] Synthesis of a diquart having a ricinoleic acid-oleic acid dimer counterion using a chloroacetic acid ester derivative of a castor oil-based estolide.

[1709] 100g of the solution of Example 30 (0.000323mol Cl) in a 500ml beaker equipped with a magnetic stirrer - 18.19 g (0.0323 mol) of the ricinoleic acid-oleic acid dimer of Synthesis Example 1, 5.5 g of deionized water, and 1.16 g of NaOH were mixed for 1 hour.

[1710] A second mixture of the same composition was prepared.

[1711] The two mixtures were combined and volatile substances were removed (40 o C / 20mbar / 4hrs).

[1712] A brown viscous material having the following structure was obtained:

[1713]

[1714] R1 (connected to the two R2-containing ingredients above) =

[1715]

[1716] Here, the two anions of the structural formula below have counterions.

[1717]

[1718] R2=

[1719]

[1720] The formed sodium chloride precipitates during storage.

[1721] Example 31

[1722] Synthesis of Hexa-tertiary Amines

[1723] 22.89 g (0.1669 mol epoxy groups, specifically epoxy content 0.00729 mol epoxy groups / 1 g) glycerol diglycidyl ether, 31.26 g (0.1669 mol NH groups) (CH3)2NCH2CH2CH2NHCH2CH2CH2N(CH3)2, and 450 g of propylene glycol monomethyl ether were mixed at room temperature in a 1000 ml three-necked bottle equipped with a reflux condenser, thermometer, magnetic stirrer, and N2 inlet / outlet. The mixture was heated to 110°C for 8 hours. The complete conversion of the epoxy groups 1 It was confirmed by H NMR spectroscopy.

[1724] A 10.74% active brown solution containing 0.99299 mmol amine / 1 g solution was obtained.

[1725] Approximate structure of hexa-tertiary amines:

[1726]

[1727] Example 31a

[1728] Synthesis of Hexa-tertiary Amines

[1729] 11.83 g (0.1169 mol epoxy groups) 1,4-butanediol diglycidyl ether, 21.91 g (0.1169 mol NH groups) (CH3)2NCH2CH2CH2NHCH2CH2CH2N(CH3)2, and 221.87 g of propylene glycol monomethyl ether were mixed at room temperature in a 500 ml three-necked bottle equipped with a reflux condenser, thermometer, magnetic stirrer, and N2 inlet / outlet. The mixture was heated to 115°C for 10 hours. The complete conversion of the epoxy groups is 1It was confirmed by H NMR spectroscopy.

[1730] A yellow solution containing 1.3815 mmol amine / 1 g solution was obtained.

[1731] Approximate structure of hexa-tertiary amines:

[1732]

[1733] Synthesis Example 32

[1734] Synthesis of tetra-quat using chloroacetic acid ester derivatives of castor oil-based estolides

[1735] 216 g of the solution of Example 31, 220 g (0.143 mol) of the castor oil-based chloroacetic acid ester intermediate described in Example 30, and 55.2 g of propylene glycol monomethyl ether were mixed at room temperature in a 1000 ml three-necked bottle equipped with a reflux condenser, a thermometer, a mechanical stirrer, and N2 inlet / outlet. The temperature was increased to 115°C for 25 hours. Afterward, volatile substances were removed under reduced pressure (60°C / 20 mbar / 4 hrs).

[1736] Essentially, a brown, transparent, viscous oil having the approximate structure below was obtained:

[1737]

[1738] Here, the four anions and counterions are Cl - have.

[1739] R1=

[1740]

[1741] R2=

[1742]

[1743] Synthesis Example 32a

[1744] Synthesis of tetra-quart having ricinoleic acid-oleic acid dimer counterions using chloroacetic acid ester derivatives of castor oil-based estolides

[1745] 100 g of tetra-quart of Example 32, 32.60 g of ricinoleic acid-oleic acid dimer of Synthesis Example 1 (0.057906 mol COOH), 2.08 g of NaOH, and 5.5 g of deionized water were placed in a 500 ml single-neck bottle. The composition was mixed in a rotary evaporator at atmospheric pressure for 2 hours. Afterward, volatile substances were removed at 40°C / 20 mbar / 2 hrs.

[1746] A brown viscous substance having the following approximate structure was obtained:

[1747]

[1748] Here, it has the following four anions and counterions.

[1749]

[1750] R1=

[1751]

[1752] R2=

[1753]

[1754] The formed sodium chloride precipitates during storage.

[1755] Synthesis Example 32b

[1756] Synthesis of tetra-quats having additional amine salt groups using chloroacetic acid ester derivatives of castor oil-based estolides

[1757] 100.40 g (0.02906 mol tertiary amine) of the tetra-quadrate of Example 32, 16.36 g (0.02906 mol COOH) of the ricinoleic acid-oleic acid dimer of Synthesis Example 1, and 5.5 g of deionized water were placed in a 500 ml single-neck bottle. The composition was mixed in a rotary evaporator at atmospheric pressure for 2 hours. Afterward, volatile substances were removed at 40°C / 20 mbar / 2 hrs.

[1758] A brown viscous substance having the following approximate structure was obtained:

[1759]

[1760] Here, the four anions and counterions Cl- It has the following two anions and counterions.

[1761]

[1762] R1=

[1763]

[1764] R2=

[1765]

[1766] Example 33

[1767] Synthesis of di-quart using chloroacetic acid ester derivatives of castor oil-based estolides

[1768] 216 g of the solution of Example 31, 145.95 g (0.0695 mol) of the castor oil-based chloroacetic acid ester intermediate described in Synthesis Example 7, and 168 g of propylene glycol monomethyl ether were mixed at room temperature in a 1000 ml three-necked bottle equipped with a reflux condenser, a thermometer, a mechanical stirrer, and an N2 inlet / outlet. The temperature was increased to 115°C for 32 hours. Afterward, volatile substances were removed under reduced pressure (60°C / 20 mbar / 3 hrs).

[1769] Essentially, a brown, transparent, viscous oil having the approximate structure below was obtained:

[1770]

[1771] Here, the two anions and counterions Cl - has

[1772] R1=

[1773]

[1774] R2=

[1775]

[1776] Synthesis Example 33a

[1777] Synthesis of a di-quart having two additional amine salt groups using a chloroacetic acid ester derivative of a castor oil-based estolide

[1778] 86.36 g of the di-quart of Example 33, 19.99 g of the ricinoleic acid-oleic acid dimer of Synthesis Example 1 (0.0355 mol COOH), and 5.5 g of deionized water were placed in a 500 ml single-neck bottle. The composition was mixed in a rotary evaporator at atmospheric pressure for 2 hours. Afterward, volatile substances were removed at 40°C / 20 mbar / 2 hrs.

[1779] A brown viscous substance having the following approximate structure was obtained:

[1780]

[1781] Here, the two anions and counterions Cl - It has the following two anions and counterions.

[1782]

[1783] R1=

[1784]

[1785] R2=

[1786]

[1787] Synthesis Example 33b

[1788] Synthesis of a di-quart having four additional amine salt groups using a chloroacetic acid ester derivative of a castor oil-based estolide

[1789] 73.45 g of the di-quart of Example 33, 34.01 g of the ricinoleic acid-oleic acid dimer of Synthesis Example 1 (0.0604 mol COOH), and 4.04 g of deionized water were placed in a 500 ml single-neck bottle. The composition was mixed in a rotary evaporator at atmospheric pressure for 2 hours. Afterward, volatile substances were removed at 40°C / 20 mbar / 2 hrs.

[1790] A brown viscous substance having the following approximate structure was obtained:

[1791]

[1792] Here, the two anions and counterions Cl - It has the following four anions and counterions.

[1793]

[1794] R1=

[1795]

[1796] R2=

[1797]

[1798] Example 34

[1799] Synthesis of di-quart using chloroacetic acid ester derivatives of castor oil-based estolides

[1800] 217.19 g of the solution of Example 31a, 210 g (0.1 mol) of the castor oil-based chloroacetic acid ester intermediate described in Synthesis Example 7, and 50 g of propylene glycol monomethyl ether were mixed at room temperature in a 1000 ml three-necked bottle equipped with a reflux condenser, a thermometer, a mechanical stirrer, and N2 inlet / outlet. The temperature was increased to 115°C for 34 hours. Afterward, volatile substances were removed under reduced pressure (60°C / 20 mbar / 4 hrs).

[1801] Essentially, a brown, transparent, viscous oil having the approximate structure below was obtained:

[1802]

[1803] Here, the two anions and counterions Cl - has

[1804] R1=

[1805]

[1806] R2=

[1807]

[1808] Synthesis Example 34a

[1809] Synthesis of a tetra-quat having two additional oleate amine salt groups using a chloroacetic acid ester derivative of a castor oil-based estolide

[1810] 116.13 g of the di-quart of Example 34, 13.29 g of oleic acid (0.047 mol COOH), and 6.39 g of deionized water were placed in a 500 ml single-neck bottle. The composition was mixed in a rotary evaporator at atmospheric pressure for 2 hours. Afterward, volatile substances were removed at 40°C / 20 mbar / 2 hrs.

[1811] A brown viscous substance having the following approximate structure was obtained:

[1812]

[1813] Here, the two anions and counterions Cl - It has the following two anions and counterions.

[1814]

[1815] R1=

[1816]

[1817] R2=

[1818]

[1819] Synthesis Example 34b

[1820] Synthesis of a tetra-quat having two additional ricinoleic acid-oleic acid dimeramine salt groups using a chloroacetic acid ester derivative of a castor oil-based estolide.

[1821] 110.47 g of the di-quart of Example 34, 25.19 g of the ricinoleic acid-oleic acid dimer of Synthesis Example 1 (0.0447 mol COOH), and 6.08 g of deionized water were placed in a 500 ml single-neck bottle. The composition was mixed in a rotary evaporator at atmospheric pressure for 2 hours. Afterward, volatile substances were removed at 40°C / 20 mbar / 2 hrs.

[1822] A brown viscous substance having the following approximate structure was obtained:

[1823]

[1824] Here, the two anions and counterions Cl - It has the following two anions and counterions.

[1825]

[1826] R1=

[1827]

[1828] R2=

[1829]

[1830] Example 35

[1831] Synthesis of di-quart using chloroacetic acid ester derivatives of castor oil-based estolides

[1832] 120.36 g of the solution of Example 31, 167.62 g (0.0797 mol) of the castor oil-based chloroacetic acid ester intermediate described in Synthesis Example 7a, and 80.6 g of propylene glycol monomethyl ether were mixed at room temperature in a 1000 ml three-necked bottle equipped with a reflux condenser, a thermometer, a mechanical stirrer, and an N2 inlet / outlet. The temperature was increased to 115°C for 31 hours. Afterward, volatile substances were removed under reduced pressure (60°C / 15 mbar / 1.5 hrs).

[1833] A brown waxy substance with the following approximate structure was obtained:

[1834]

[1835] Here, the two anions and counterions Cl - has

[1836] R1=

[1837]

[1838] R2=

[1839]

[1840] Synthesis Example 35a

[1841] Synthesis of a di-quart having two additional amine salt groups using a chloroacetic acid ester derivative of a castor oil-based estolide

[1842] 85.42 g of the di-quart of Example 35, 10.4 g of the ricinoleic acid-stearic acid dimer of Synthesis Example 2a (0.0184 mol COOH), and 4.7 g of deionized water were placed in a 500 ml single-neck bottle. The composition was mixed in a rotary evaporator at atmospheric pressure for 2 hours. Afterward, volatile substances were removed at 40°C / 20 mbar / 2 hrs.

[1843] A brown waxy substance with the following approximate structure was obtained:

[1844]

[1845] Here, there are two anions and counterions Cl-, and the following two anions and counterions.

[1846]

[1847] R1=

[1848]

[1849] R2=

[1850]

[1851] Synthesis Example 35b

[1852] Synthesis of a di-quart having two additional amine salt groups using a chloroacetic acid ester derivative of a castor oil-based estolide

[1853] 89.30 g of the di-quart of Example 35, 5.43 g of oleic acid (0.01924 mol COOH), and 4.7 g of deionized water were placed in a 500 ml single-neck bottle. The composition was mixed in a rotary evaporator at atmospheric pressure for 1 hour. Afterward, volatile substances were removed at 40°C / 20 mbar / 2 hrs.

[1854] A brown waxy substance with the following approximate structure was obtained:

[1855]

[1856] Here, there are two anions and counterions Cl-, and the following two anions and counterions.

[1857]

[1858] R1=

[1859]

[1860] R2=

[1861]

[1862] Example of a scalable process

[1863] Example 36

[1864] Synthesis of (ricinoleic acid-stearic acid)dimer acid-containing mixtures

[1865] 163.45 g (0.5746 mol) of stearic acid was heated to 70°C in a 500 ml three-necked bottle equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, N2 inlet, and vacuum outlet. A gentle N2 stream flowed through the bottle while the reaction proceeded. 81.66 g (0.2736 mol) of ricinoleic acid, containing 15% oleic acid and having a theoretical value of 70% free OH groups, was added. The mixture was heated to 160°C for 1 hour. Additionally, 163.34 g (0.5417 mol) of ricinoleic acid was added at 160°C for 1 hour, and the temperature was maintained for 5 hours. Afterward, the temperature was raised to 200°C and maintained for 17 hours.

[1866] The complete conversion of the OH group is 1 It was confirmed by H NMR spectroscopy.

[1867] A grayish-brown wax containing a ricinoleic acid-stearic acid dimer as the main component was obtained.

[1868] Ricinoleic acid-stearic acid dimer (main component approx. 80%)

[1869]

[1870] Risinoleic acid-Risinoleic acid-Stearic acid trimer (approx. 10%)

[1871]

[1872] Additionally, a total of approximately 10% (ricinoleic acid) 3-6- Stearic acid, ricinoleic acid dimer, ricinoleic acid, stearic acid type acid.

[1873] Example 36a

[1874] Synthesis of chloroacetic acid ester derivatives of castor oil-based estolides

[1875] 30 g (0.0321 mol) of castor oil was placed in a 100 ml three-necked bottle equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel, N2 inlet, and gas vent tube, and heated to 80°C. A smooth N2 stream flowed through the bottle while the reaction proceeded. During stirring, 4.25 g (0.0449 mol) of chloroacetic acid was added. The temperature was raised to 120°C and maintained for 6 hours. Subsequently, the temperature was raised to 140°C and maintained for 5 hours. The formation of approximately 0.85 chloroacetic acid ester bonds per molecule of castor oil 1 It was confirmed through H NMR spectroscopy.

[1876] 0.46 g of chloroacetic acid (0.0048 mol) was added, and the reaction was continued at 140°C for an additional 8 hours.

[1877] The formation of approximately one chloroacetic acid ester bond per castor oil molecule 1 It was confirmed through H NMR spectroscopy.

[1878] Excess chloroacetic acid was removed under reduced pressure (140℃ / 25mbar).

[1879] 36.31 g (0.0643 mol) of (ricinoleic acid)1-stearic acid dimer acid of Synthesis Example 36 was added. The temperature was raised to 200°C and maintained for 17 hours.

[1880] The complete conversion of the OH groups of the castor oil molecule and the formation of additional ester moiety are 1 It was confirmed by H NMR spectroscopy.

[1881] Essentially, a brown wax-like substance having the approximate structure below was obtained:

[1882]

[1883] R1=

[1884]

[1885] R2=

[1886]

[1887] Example 36b

[1888] Synthesis of tetra-quat using chloroacetic acid ester derivatives of castor oil-based estolides

[1889] 16.75 g (0.0166 mol tertiary amine) of the tertiary amino solution of Example 31, 23.33 g (0.0111 mol Cl) of the castor oil-based chloroacetic acid ester intermediate of Example 36a, and 10.18 g of propylene glycol monomethyl ether were mixed at room temperature in a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, and a mechanical stirrer. The temperature was increased to 115°C for 24 hours. Afterward, volatile substances were removed under reduced pressure (60°C / 15 mbar / 1.5 hrs).

[1890] A brown waxy substance with the following approximate structure was obtained:

[1891]

[1892] Here, the four anions and counterions Cl - has

[1893] R1=

[1894]

[1895] R2=

[1896]

[1897] Synthesis Example 37a

[1898] (Ricinoleic acid 2 -butanediol-ricinoleic acid 2 Synthesis of pentameridol

[1899] 7.22 g (0.080 mol) of 1,4-butanediol and 47.82 g (0.16 mol) of ricinoleic acid were mixed in a 100 ml three-necked bottle equipped with a reflux condenser, thermometer and magnetic stirrer, dropping funnel, N2 inlet and gas / vacuum outlet, and heated to 160°C for 17 hours. A gentle N2 flow passed through the gas volume above the liquid surface.

[1900] 42.16 g (0.065 mol) of the intermediate with the approximate structure below and 38.66 g (0.13 mol) of ricinoleic acid were placed in separate bottles and heated at 160°C for 10 hours. Afterward, the temperature was increased to 200°C for 6 hours. During this reaction process, a gentle N2 flow passed through the gas volume above the liquid surface.

[1901]

[1902] A yellowish-brown liquid was obtained with the following average structure as the main component.

[1903]

[1904] R1

[1905]

[1906] Example 37b

[1907] (Ricinoleic acid 2 -butanediol-ricinoleic acid 2 Synthesis of D-Quart using chloroacetic acid ester derivatives of pentamer diol

[1908] 2.07 g (1.708 mmol) of the 1,4-butanediol-based pentamer diol of Example 37a and 0.44 g (3.928 mmol) of chloroacetic acid chloride were mixed at room temperature in a 50 ml three-necked bottle equipped with a reflux condenser, thermometer, mechanical stirrer, and N2 inlet / outlet. The temperature was increased to 70°C for 5 hours. Afterward, volatile substances were removed under reduced pressure (70°C / 15 mbar / 1 h).

[1909] An intermediate of the following average structure was obtained.

[1910]

[1911] R1:

[1912]

[1913] 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 hours. Volatile substances were removed under reduced pressure (60°C / 15 mbar / 1 h). The quantitative conversion of the CH2Cl group is 1 It was determined by H-NMR spectroscopy.

[1914] A yellow liquid wax material having the following approximate structure was obtained:

[1915]

[1916] R1

[1917]

[1918] Here, the two anions and counterions Cl - has

[1919] Additional application test

[1920] Damaged human hair

[1921]

[1922] The data in the two tables above regarding damaged human hair show that the compounds according to the present invention can reduce combability on different keratin substrates. The data for compounds 30b and 32a regarding damaged human hair highlight the efficacy of the materials of the present invention having polyfatty acid matrix in both the cation and the anion simultaneously as substitutes for inorganic anions. The data for compounds 33a, 33b, 34a, and 34b highlight the value of amine base groups in addition to quart groups when applied to damaged human hair. The data for compounds 35a and 35b highlight the value of structures having a higher melting portion in polyfat chains.

[1923] Hair Conditioner Application Test:

[1924] Hair conditioner formulation

[1925]

[1926] *: The amount of a given component refers to “parts by weight based on 100 parts by weight of the total composition.”

[1927] procedure:

[1928] Phase A and Phase B were heated separately at 80°C (Phase A) and 60°C (Phase B), respectively. Phase A was mixed with Phase B.

[1929] After addition, the mixture was stirred at 60°C for 30 minutes. Phase C was added and the reaction temperature was raised to 250°C. Phase D was stirred for 15 minutes. The composition was stored in a suitable container.

[1930] Combing Analysis:

[1931] Each conditioner is evaluated in duplicate, and the average, as shown in the following data, is considered for the conclusion.

[1932] Combing force measurement procedure:

[1933] Combing force measurements were performed using the Dia-Stron MTT 175 (Dia-Stron Limited) as described for the combing force measurements above.

[1934] 1. Asian hair bundles (2.5 gm) were pre-washed with 2% NaOH and then washed with 10% SLES.

[1935] 2. The total work performed in wet and dry combing was measured.

[1936] Here, "total work performed" is defined as the work done while moving the comb across the hair and is measured by the Dia-Stron MTT175.

[1937] 3. After washing the hair with 350 mg of conditioner, it was thoroughly rinsed with lukewarm water.

[1938] 4. The total work p...

Claims

Claim 1 Compound of chemical formula (I): R 1 (-F) x (I), where x is 2 to 50, and R 1 is selected from arbitrarily substituted hydrocarbon radicals of x, having up to 1000 carbon atoms, -O-, -NH-, -C(O)-, -C(S)-, tertiary amino group ( It may optionally contain one or more groups selected from ), and may be substituted with one or more groups selected from OH groups and halogen groups, F may be the same or different, and is represented by chemical formula (II), Here, the F units are R 1 Bonded to the carbon atom of, n is 0, and R 3 , R 4 , R 5 It may be identical or different and may be selected from hydrogen and optionally substituted straight-chain, cyclic or branched, saturated, unsaturated, or aromatic hydrocarbon radicals having up to 1000 carbon atoms, and -O-, -NH-, -C(O)-, -C(S)-, tertiary amino group ( It optionally contains one or more groups selected from ), and can be substituted with one or more groups selected from OH groups and halogen groups, where R 3 , R 4 , R 5 Each is bonded to the nitrogen atom as a carbon atom, and the counterion A of the ammonium ion - is selected from monovalent to trivalent inorganic anions and monovalent to 30,000-valent organic anions, and R present in the cation structures of chemical formulas (I) and (II). 1 , R 3 , R 4 , R 5 At least one of them contains at least one moiety of chemical 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 to 20, X is O, and R 6 is independently selected from optionally substituted straight-chain, cyclic, or branched, saturated or unsaturated hydrocarbon radicals having 1 to 36 carbon atoms, provided that at least one R 6 It has more than 6 carbon atoms. Claim 2 delete Claim 3 delete Claim 4 In claim 1, R 1 is a compound containing at least one moiety of formula (IIIa) or formula (IVa): (-XC(O)-R 6 ) m -XC(O)-R 7 (IIIa), (-C(O)-XR 6 ) m -C(O)-XR 7 (IVa) Here, X and R 6 and m are as defined in claim 1, and R 7 is independently selected from optionally substituted straight-chain, cyclic, or branched, saturated or unsaturated hydrocarbon radicals having 1 to 36 carbon atoms, and -O-, -NH-, -C(O)-, -C(S)-, tertiary amino group ( Optionally containing one or more groups selected from ), and may be substituted with an OH group or a halogen group, wherein radical R 7 It cannot contain a combination of -C(O)- groups and -O- groups forming an internal carboxylate group or an internal amide group, or a combination of -C(O)- groups and -NH- or tertiary amino groups. Claim 5 delete Claim 6 delete Claim 7 delete Claim 8 delete Claim 9 A compound according to claim 1 or 4, wherein x in formula (I) is 2 and formula (V): Here, R 1 , R 3 , R 4 , R 5 and n are as defined above. Claim 10 In claim 1 or 4, F has the formula (VI), and the F groups are R 1 Compounds that bond to carbon atoms: Here R 3 , R 4 , R 5 is independently selected from hydrogen and optionally substituted straight-chain, cyclic, or branched, saturated, unsaturated, or aromatic hydrocarbon radicals, having up to 300 carbon atoms, -O-, -NH-, -C(O)-, -C(S)-, tertiary amino group ( Optionally containing one or more groups selected from ), which can be substituted with OH, and counterion A - It is selected from monovalent to trivalent inorganic anions and monovalent to 30,000valent organic anions. Claim 11 delete Claim 12 delete Claim 13 In claim 4, R 1 Silver is selected from poly(alkylene oxide) groups: provided that the sum of the carbon atoms of such poly(alkylene oxide) groups is 2 to 100, or R 1 Silver is selected from divalent hydrocarbon groups derived from oligoglycerols of chemical formula (X):-[CH2CH(R 8 )CH2O] t1 -[CH2CH(R 8 )CH2)] t2 - (X) Here, t1 = 0 to 32, t2 = 1, and R 8 = OH or (-XC(O)-R 6 ) m -XC(O)-R 7 and, here m, X, R 6 and R 7 ...is as defined above, provided that the sum of carbon atoms is 2 to 100, or R 1 Silver is selected from divalent hydrocarbon groups comprising at least one ester group of formulas (XI) and (XII):-[CH2CH2O] q1 -R 9 -[CH2CH2O] q1 -[CH2CH2] q2 - (XI)Here, q1 is the same or different, is between 0 and 49, q2=1, and -[CH2CH(R 8 )CH2O] t1 -R 9 -[CH2CH(R 8 )CH2O] t1 -[CH2CH(R 8 )CH2)] t2 - (XII) Here, t1, t2 and R 8 is as defined above, and R 9 -C(O)C(O)O-, -C(O)(CH2) 1-8 Derived from C(O)O-, -C(O)(C6H4)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-, provided that R 9 A compound in which the sum of carbon atoms is 2 to 100. Claim 14 In claim 1 or 4, N + Radical R bonded to 1 , R 3 , R 4 , R 5 If one or more of them contain at least one moiety of 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 to 20 and X and R 6 is as defined above, and at least one moiety has the structure of chemical formula (XIII) or (XIV), and -R 10 (-XC(O)-R 6 ) m -XC(O)- (XIII) or -R 10 (-C(O)-XR 6 ) m -C(O)-X- (XIV), where R 10 It is selected from optionally substituted hydrocarbon radicals of 2 to 18 valence, having up to 200 carbon atoms, -O-, -NH-, -C(O)-, -C(S)-, tertiary amino group ( It may optionally contain one or more groups selected from ), and may be substituted with -OH or a halide group, where radical R 10 It may not contain a combination of -C(O)- and -O- groups forming an internal carboxylate group or an internal amide group, or a combination of -C(O)- and -NH- or tertiary amino groups, provided, R 10 N by a single bond + A compound that is connected to a moiety. Claim 15 delete Claim 16 delete Claim 17 In claim 14, the low-melting point and high-melting point fatty acids of C5 or higher contain ester components of formulas (III) and (IV) R 6 Located within, (-XC(O)-R 6 ) m -XC(O)- (III) (-C(O)-XR 6 ) m R containing -C(O)-X- (IV), or ester components of chemical formulas (XIII) and (XIV). 6 Located within, R 10 (-XC(O)-R 6 ) m -XC(O)- (XIII) -R 10 (-C(O)-XR 6 ) m -C(O)-X- (XIV), where C5 or higher low-melting point fatty acids are defined as having a melting point ≤ 40°C, C5 or higher high-melting point fatty acids are defined as having a melting point > 40°C, and in the manner as follows— at least one C5 or higher low-melting point fatty acid is each R 6 Forming, and R of chemical formula (III) or (IV) 6 - Located at one end of the ester component containing, while at least one C5 or higher high melting point fatty acid is located at the opposite end of the ester component of formula (III) or (IV) a radical or radical R 6 Forms, or at least one C5 or higher high-melting-point fatty acid, each R 6 Forming, and R of chemical formula (III) or (IV) 6 - Located at one end of the ester component containing, while at least one C5 or lower melting point fatty acid is located at the opposite end of the ester component of formula (III) or (IV) a radical or radical R 6 It is a method of forming, or—at least one C5 or higher low-melting point fatty acid is each R 6 It forms, and radical R 10 Located adjacent to, on the other hand, at least one C5 or higher high-melting-point fatty acid is a radical or radical R at the opposite end of the ester component of formula (XIII) or (XIV). 6 Forms, or at least one C5 or higher high-melting-point fatty acid is each R 6 Forms, and R 10 Radical or radical R adjacent to 6 It forms, while at least one C5 or lower melting point fatty acid is R of formula (XIII) or (XIV). 6 - Radical or radical R at the opposite end of the contained ester component 6 A compound that is a method of forming. Claim 18 delete Claim 19 delete Claim 20 delete Claim 21 A compound according to claim 1 or 4, wherein the compound does not contain an amide group. Claim 22 In claim 1 or 4, R present in the cation structures of formulas (I) and (II). 1 , R 3 , R 4 , R 5 At least one of them contains at least one moiety of the chemical formula below, and R 1* [(-OC(O)- R 6 ) m -OC(O)-]2 Here R 1* ≡ 2 is a C1-C100 radical, m is independently up to 12, and R 6 A compound that is as defined above. Claim 23 delete Claim 24 delete Claim 25 In claim 22, R present in the cation structures of formulas (I) and (II). 1 , R 3 , R 4 , R 5 At least one of the groups contains at least one moiety of the chemical formula below, and R 1* [(-OC(O)- R 6 ) m -OC(O)-R 7* -]2 Here R 1* , R 6 , and m are as defined above, and R 7* A compound that is a C1-C12 alkylene group. Claim 26 delete Claim 27 delete Claim 28 In claim 25, chemical formula R 1* [(-OC(O)- R 6 ) m -OC(O)-R 7* At least one moiety of -]2 has one or both terminal R 7* A compound that is bonded to a quaternary N atom in the group, wherein the compound is a di-quad or tetra-quad compound. Claim 29 delete Claim 30 delete Claim 31 In claim 1 or 4, the group R present in the cation structure of formulas (I) and (II). 1 , R 3 , R 4 , R 5 At least one of them contains at least one moiety of the following chemical 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 is as defined above, l is an integer independently selected from 0 to 20, L is a divalent hydrocarbon radical, which can have 1 to 30 carbon atoms, and -O-, -S-, -NH-, -C(O)-, -C(S)- and tertiary amino groups ( A compound that may optionally contain one or more of the groups ). Claim 32 delete Claim 33 delete Claim 34 delete Claim 35 delete Claim 36 Method for synthesizing a compound of formula (I) of claim 1 or 4: R 1 (-F) x (I) Here, an alkyl halide reacts with a tertiary amine containing at least one of the following moiety, (-XC(O)-R 6 ) m -XC(O)- (III) or (-C(O)-XR 6 ) m -C(O)-X- (IV), or an ester of a halogen carboxylic acid and an alcohol or epoxide react with a tertiary amine containing at least one of the following moiety, (-XC(O)-R 6 ) m -XC(O)- (III) or (-C(O)-XR 6 ) m -C(O)-X- (IV), or epoxy-functionalized ethers and esters and alcohols or carboxylic acids react with a tertiary amine containing at least one of the following moiety in the presence of acid, (-XC(O)-R 6 ) m -XC(O)- (III) or (-C(O)-XR 6 ) m -C(O)-X- (IV), or a hydrocarbon containing a tertiary amino group reacts with an ester of a halogen carboxylic acid containing at least one of the following moiety, (-XC(O)-R 6 ) m -XC(O)- (III) or (-C(O)-XR 6 ) m -C(O)-X-(IV), or a hydrocarbon containing a tertiary amino group reacts with an epoxy-functionalized ether and ester containing at least one of the following moiety in the presence of acid, (-XC(O)-R 6 ) m -XC(O)- (III) or (-C(O)-XR 6 ) m -C(O)-X- (IV), where X, R 6 , m and x are as defined above. Claim 37 delete Claim 38 delete Claim 39 delete Claim 40 delete Claim 41 A composition containing the compound of claim 1 or 4 for hair treatment selected from the group consisting of hair shampoo compositions, hair conditioning compositions, hair strengthening compositions, hair coloring or dyeing compositions, hair combing improvement compositions, frizz prevention compositions, and hair rinse-off and leave-on compositions.

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