Fibrous amino acid-based substrates, especially polymeric fatty acid salt compounds for hair treatment

Abstract

The present invention relates to a method for the preparation of a carboxylate anion (COO) selected from the group consisting of an organic ammonium group-containing cation that does not contain an estolide moiety, and an anion that contains at least one estolide moiety or a carboxylate anion that contains at least one internal ester group. - The invention is also directed to organic ammonium salts comprising an anion containing a 1-aminoethyl 1-propanediol group and an anion containing a 1-aminoethyl 1-propanediol group. The invention is also directed to processes for the preparation of such organic ammonium salts, the use of such organic ammonium salts in cosmetic skin care and hair care formulations, the use of such organic ammonium salts for the treatment of fibers, the use of organic ammonium salts for the treatment of hair, compositions comprising such organic ammonium salts, the use of the products of this process for the preparation of organic ammonium salts in cosmetic formulations for skin care and hair conditioners and hair shampoos, the use of said products for the treatment of fibers, and compositions comprising said products for the treatment of hair.

Description

[Technical field]

[0001] The present invention relates to polymeric fatty acid salt compounds, processes for their preparation, compositions containing the polymeric fatty acid salt compounds, and cosmetic compositions comprising the polymeric fatty acid salt compounds for skin care and hair care, in particular the use of the polymeric fatty acid salt compounds in hair care compositions, and their use for treating hair. [Background technology]

[0002] Hair may generally be straight, wavy, curly, kinky, or kinky. Human hair contains three main morphological components: the cuticle (a thin outermost shell consisting of multiple concentric layers), the cortex (the body of the hair), and in thicker hairs, the medulla (a thin central core). The cuticle and cortex determine the mechanical properties of the hair, i.e., its tendency to wave, curl, or kink. Straight hair resembles a rod with a circular cross section, wavy hair appears compressed to have an oval cross section, curly hair is further compressed to look like an elongated oval cross section, and kinky hair may have a flatter cross section.

[0003] The main component of hair is the cross-linked α-helical protein keratin. Keratin is an intermediate filament protein found specifically in epithelial cells, e.g. in human skin and hair, wool, feathers, and nails. Alpha-helical type I and type II keratin intermediate filament proteins (KIFs) with molecular weights of about 45-60 kDa are embedded in an amorphous matrix of keratin-associated proteins (KAPs) with molecular weights of 20-30 kDa (MA Rogers, L. Langbein, S. Praetzel-Wunder, H. Winter, J. Schweizer, International Journal of Cytology 2006;251:209-6); both intra- and intermolecular disulfide bonds provided by cystine contribute to the cytoskeletal protein network that maintains the scaffolding of the cells. In addition to disulfide bridges, ionic bonds or salt bridges that pair different amino acids contained in hair proteins contribute to the outer shape of the hair.

[0004] It is known in the art that hair can be treated with functionalized silicones and hydrocarbons that provide one or more cosmetic benefits, such as conditioning, shine and UV protection, and color retention. Typically, these silicone and hydrocarbon-based derivatives are physically deposited on the fiber surface (cuticle), thus affecting the appearance of the hair, i.e. smoothness, shine, friction, alignment, combability, etc.

[0005] High-performance silicone derivatives are generally considered high-performance materials with respect to properties such as smooth and silky hair feel, reduced friction, easy combing, hair color protection, etc. Each of the quaternized silicones is described in the prior art disclosures, namely U.S. Pat. No. 4,891,166, European Patent No. 282,720, U.S. Patent Publication No. 2008027202, U.S. Pat. No. 6,730,766, U.S. Pat. No. 6,240,929, WO 02 / 10257, WO 02 / 10259, WO 2004 / 069137, WO 2013 / 148629, WO 2013 / 148635, WO 2013 / 148935.

[0006] Hydrocarbon-based conditioning agents are also widely used.Typically, the monoquaternary ammonium compound is a mono-long alkyl tri-short alkyl quaternary ammonium salt or a di-long alkyl di-short alkyl quaternary ammonium salt, in which one or two alkyl substituents are selected from an aliphatic group of about 8 to about 30 carbon atoms, or an aromatic, alkoxy, polyoxyalkylene, alkylamide, hydroxyalkyl, aryl or alkylaryl group having up to about 30 carbon atoms; the other alkyl group is independently selected from an aliphatic group of about 1 to about 8 carbon atoms, or an aromatic, alkoxy, polyoxyalkylene, alkylamide, hydroxyalkyl, aryl or alkylaryl group having up to about 8 carbon atoms; the counterion is a salt-forming anion selected from the radicals of halogen (e.g., chloride, bromide), acetate, citrate, lactate, glycolate, phosphate, nitrate, sulfonate, sulfate, alkyl sulfate, glutamate, and alkyl sulfonate. Alternatively, these monoquaternary ammonium compounds are mono- and di-fatty acid ester quats (quaternized products) of saturated or unsaturated fatty acids, as well as fatty acid amide quats having 10 to 24 carbon atoms in the alkyl chain. Details of these materials containing quaternary ammonium groups are disclosed, for example, in U.S. Patent Publication No. 2009 / 0000638, WO 2012 / 027369, U.S. Patent Publication No. 2013 / 259820, and U.S. Patent Nos. 5,880,086, 6,465,419, 6,462,014, 6,323,167, 6,037,315, 5,854,201, 5,750,490, 5,463,094, and U.S. Patent Publication No. 2003 / 013627.

[0007] Diquaternary hydrocarbons are also known. Typically, these gemini quats are based on C8 to C20 alkyl or aliphatic chains (D. Shukla et al., Cationic Di-Surfactants: A Review, Journal of the Japanese Oil Chemist's Society 2006, Vol. 55, No. 8, 381-390; M. J. Rosen et al., Langmuir (2001), 17, 6148-6154).

[0008] Diquaternized hydrocarbons based on alternating copolyesters of castor oil and various dicarboxylic acids are described in US Patent Publication No. 2003 / 0007950 and US Pat. No. 6,972,123.

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

[0010] Fatty acid dimers have been used to synthesize polyquaternary fatty acid dimer copolymers (US Pat. No. 6,982,078).

[0011] WO 2004 / 093834 describes hydrocarbon monoquaternary compounds for personal care applications. These compounds include those having the structure -CH 2 CH 2 O-EO x -PO y A -containing linking group is essential. Polymerized fatty acids have been proposed as hydrophobic tails.

[0012] US Patent No. 6,051,214 proposes a shampoo based on a cleansing surfactant, a thickener, water, and an estolide, and also proposes a conditioner containing a conditioning agent, a thickener, water, and an estolide.

[0013] There is a need for efficient compounds for fibrous amino acid-based substrates, especially for hair treatment, that can be synthesized in a simple, cost-effective and versatile way, based mainly on sustainable raw materials, that are easy to formulate and use, that give stable formulations over time even in the presence of other functional ingredients, and that are useful for conditioning the hair, improving dry and wet combing, smoothing and comfortable styling of the hair. In particular, advantages in terms of improving wet and dry combing, close to those of silicone-based conditioning agents, must be achieved.

[0014] The present inventors have found that a novel salt compound of a polymeric fatty acid containing a carboxylate anion with an estolide structure and an aqueous composition containing such a salt compound are suitable for meeting the above-mentioned needs.Therefore, the present invention provides a novel salt compound of a polymeric fatty acid containing a carboxylate anion with an estolide structure, an aqueous composition containing the same, a cosmetic composition containing the same, particularly a hair care composition, and their use for hair treatment, and the salt compound of a polymeric fatty acid containing a carboxylate anion with an estolide structure can be synthesized in a simple, cost-effective and versatile manner based mainly on sustainable raw materials.The compound of the present invention is easy to formulate and use, and is useful for conditioning hair, improving combability of hair when dry and wet, smoothing hair and comfortable alignment. Summary of the Invention

[0015] The present invention relates to organic ammonium salts based on fatty acids, in which the carboxylate anion is based on an estolide structure but the cation does not exhibit such a structure, as well as to a process for their preparation, compositions containing the salt compounds and cosmetic compositions containing same for skin and hair care, in particular the use of the salt compounds in hair care compositions, and their use for the treatment of hair.

[0016] Thus, according to the present invention there is provided an organic ammonium salt comprising an organic ammonium group-containing cation, With the proviso that the organoammonium group-containing cation does not contain a moiety of formula (III) or (IV): (-ZC(O)-R 6 ) r -ZC(O)- (III) or (-C(O)-ZR 6 ) r -C(O)-Z- (IV), During the ceremony Z may be the same or different and is -O- or -NR 11 - is selected from, where R 11 is hydrogen, or -O-, -NH-, -C(O)-, -C(S)-, [ka] and optionally substituted with one or more of a hydroxyl group and a halide group, optionally containing one or more groups selected from the group consisting of optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals having up to 100 carbon atoms, R 6 are independently selected from optionally substituted linear, cyclic, or branched, substituted or unsubstituted hydrocarbon radicals having 1 to 36 carbon atoms, where R 6 at least one of has more than 6 carbon atoms, and r is from 1 to 20, The carboxylate anion (COO - ) group-containing anion is selected from the group consisting of anions of formulas (V), (VII), and (X): Formula (V): R 7 (-XC(O)-G) p (V) During the ceremony R in formula (V) 7 is selected from p-valent optionally substituted hydrocarbon radicals, optionally including -O-, -NH-, -C(O)-, -C(S)-, [ka] and quaternary ammonium groups, and may contain one or more groups selected from a carboxyl (-COOH) group, a carboxylate anion (-COO - ) groups and hydroxyl (-OH) groups; p≧1, more preferably 2 to 811; X may be the same or different and is -O- or -NR 10 - selected from, where R 10 is hydrogen, or -O-, -NH-, -C(O)-, -C(S)-, [ka] or a group consisting of optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals having up to 100 carbon atoms, optionally containing one or more groups selected from the formula (V)R 10 In R 7 to form a bond to form a cyclic structure, G may be the same or different and optionally is -O-, -NH-, -C(O)-, -C(S)-, and [ka] A carboxyl (-COOH) group, a carboxylate anion (-COO - ) groups, hydroxyl (-OH) groups, and halide (-halogen) groups; with the proviso that at least one of the radicals G has the formula (VI) or (VI * ) -R 8 (-XC(O)-R 8 ) m -XC(O)-R 9 (VI) -R 8 (-XC(O)-R 8 ) m -XC(O)-R 9* (VI * ) During the ceremony X is as defined above, m=0 to 20, preferably 1 to 20; R 8are independently selected from optionally substituted linear, cyclic, or branched, substituted or unsubstituted divalent hydrocarbon radicals having up to 36 hydrocarbons; R 9 is optionally -O-, -NH-, -C(O)-, -C(S)-, [ka] and one or more groups selected from the group consisting of a carboxyl (-COOH) group, a carboxylate anion (-COO - ) groups, hydroxyl (-OH) groups, and halide (-halogen) groups, optionally substituted linear, cyclic, or branched, substituted or unsubstituted hydrocarbon radicals having from 1 to 1000 carbon atoms, which may be substituted with one or more substituents selected from the radical R 9 is the internal carboxy (-COO - ) group or (-CON(R')-, where R' is hydrogen or an organic group) amide group, i.e., R 9 cannot contain a combination of -C(O)- and -O- groups or a combination of -C(O)- and -NH- or tertiary amino groups; and However, formula (VI)R 9 in at least one moiety of formula (VI) having at least 2, preferably at least 6, carbon atoms, and in the same moiety of formula (VI) R 8 at least one of has at least 6, preferably at least 8, carbon atoms; However, R 7 and at least one of G is one or more carboxylate anions (-COO - ) group, R 9* is optionally -O-, -NH-, -C(O)-, -C(S)-, [ka] and optionally substituted branched or dendrimeric hydrocarbon radicals having from 1 to 1000 carbon atoms, which may be substituted with carboxyl, hydroxyl, or halide groups, where the radical R 9* is terminated by two or more groups of the general structure -XC(O)-T where X is as defined above, and T is a monovalent linear, cyclic, or branched, substituted or unsubstituted hydrocarbon radical of up to 36 hydrocarbons optionally substituted with carboxyl, hydroxyl, or halide groups; However, formula (VI * )R 9* is terminated by one or more groups T having at least 2, preferably at least 6, carbon atoms, and is represented by the formula (VI * ) in the same component of R 8 at least one of has at least 6, preferably at least 8, carbon atoms; In addition, R in formula (V) 7 and at least one of G is one or more carboxylate anions (-COO - ) group, Formula (VII): R 7 (-C(O)-XY) q (VII) During the ceremony R 7 and X is as defined above; q=1 to 55, preferably 1 to 40, more preferably 2 to 4, and Y may be the same or different and is optionally selected from -O-, -NH-, -C(O)-, -C(S)-, and [ka] and one or more groups selected from the group consisting of a carboxyl (-COOH) group, a carboxylate anion (-COO -) groups and hydroxyl groups, optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals having up to 1005 carbon atoms, which may be substituted by one or more substituents selected from with the proviso that at least one of the radicals Y is of formula (VIII) or (VIII * ) -R 8 (-C(O)-XR 8 ) m -C(O)-XR 9 (VIII) -R 8 (-C(O)-XR 8 ) m -C(O)-XR 9* (VIII * ) In the formula (VIII), X, m and R 8 , and R 9 are each as defined above for formula (VI), and Formula (VIII * ) in X, m, and R 8 , and R 9* are represented by the formula (VI * ) is as defined above; In addition, R in formula (VII) 7 and at least one of Y is one or more carboxylate anions (-COO - ) group, Formula (X): R 7 (-C(O)-XR 8 -COO - ) q Here, X and R in formula (X) 7 , R 8 , and q are as defined above for formulas (VII) and (VIII), respectively. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0017] The present invention will be described in detail below.

[0018] According to the present invention, there is provided an organic ammonium salt comprising an organic ammonium group-containing cation, With the proviso that the organoammonium group-containing cation does not contain a moiety of formula (III) or (IV): (-ZC(O)-R 6 ) r -ZC(O)- (III) or (-C(O)-ZR 6 ) r -C(O)-Z- (IV), During the ceremony Z may be the same or different and is -O- or -NR 11 - is selected from, where R 11 is hydrogen, or -O-, -NH-, -C(O)-, -C(S)-, [ka] and optionally substituted with one or more of a hydroxyl group and a halide group, optionally containing one or more groups selected from the group consisting of optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals having up to 100 carbon atoms, R 6 are independently selected from optionally substituted linear, cyclic, or branched, substituted or unsubstituted hydrocarbon radicals having 1 to 36 carbon atoms, where R 6 at least one of has more than 6 carbon atoms, and r is from 1 to 20, The carboxylate anion (COO - ) group-containing anion is selected from the group consisting of anions of formulas (V), (VII), and (X): Formula (V): R 7 (-XC(O)-G) p (V) During the ceremony R in formula (V) 7is selected from p-valent optionally substituted hydrocarbon radicals, optionally including -O-, -NH-, -C(O)-, -C(S)-, [ka] and quaternary ammonium groups, and may contain one or more groups selected from a carboxyl (-COOH) group, a carboxylate anion (-COO - ) groups and hydroxyl (-OH) groups; p≧1, more preferably 2 to 811; X may be the same or different and is -O- or -NR 10 - selected from, where R 10 is hydrogen, or -O-, -NH-, -C(O)-, -C(S)-, [ka] or a group consisting of optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals having up to 100 carbon atoms, optionally containing one or more groups selected from the formula (V)R 10 In R 7 to form a bond to form a cyclic structure, G may be the same or different and optionally is -O-, -NH-, -C(O)-, -C(S)-, and [ka] A carboxyl (-COOH) group, a carboxylate anion (-COO - ) groups, hydroxyl (-OH) groups, and halide (-halogen) groups; with the proviso that at least one of the radicals G has the formula (VI) or (VI * ) -R 8 (-XC(O)-R 8 ) m -XC(O)-R 9 (VI) -R 8 (-XC(O)-R 8 ) m -XC(O)-R 9* (VI * ) During the ceremony X is as defined above, m=0 to 20, preferably 1 to 20; R 8 are independently selected from optionally substituted linear, cyclic, or branched, substituted or unsubstituted divalent hydrocarbon radicals having up to 36 hydrocarbons; R 9 is optionally -O-, -NH-, -C(O)-, -C(S)-, [ka] and one or more groups selected from the group consisting of a carboxyl (-COOH) group, a carboxylate anion (-COO - ) groups, hydroxyl (-OH) groups, and halide (-halogen) groups, optionally substituted linear, cyclic, or branched, substituted or unsubstituted hydrocarbon radicals having from 1 to 1000 carbon atoms, which may be substituted with one or more substituents selected from the radical R 9 is the internal carboxy (-COO - ) group or (-CON(R')-, where R' is hydrogen or an organic group) amide group, i.e., R 9 cannot contain a combination of -C(O)- and -O- groups or a combination of -C(O)- and -NH- or tertiary amino groups; and However, formula (VI)R 9in at least one moiety of formula (VI) having at least 2, preferably at least 6, carbon atoms, and in the same moiety of formula (VI) R 8 at least one of has at least 6, preferably at least 8, carbon atoms; However, R 7 and at least one of G is one or more carboxylate anions (-COO - ) group, R 9* is optionally -O-, -NH-, -C(O)-, -C(S)-, [ka] and optionally substituted branched or dendrimeric hydrocarbon radicals having from 1 to 1000 carbon atoms, which may be substituted with carboxyl, hydroxyl, or halide groups, where the radical R 9* is terminated by two or more groups of the general structure -XC(O)-T where X is as defined above, and T is a monovalent linear, cyclic, or branched, substituted or unsubstituted hydrocarbon radical of up to 36 hydrocarbons optionally substituted with carboxyl, hydroxyl, or halide groups; However, formula (VI * )R 9* is terminated by one or more groups T having at least 2, preferably at least 6, carbon atoms, and is represented by the formula (VI * ) in the same component of R 8 at least one of has at least 6, preferably at least 8, carbon atoms; In addition, R in formula (V) 7 and at least one of G is one or more carboxylate anions (-COO - ) group, Formula (VII): R 7 (-C(O)-XY)q (VII) During the ceremony R 7 and X is as defined above; q=1 to 55, preferably 1 to 40, more preferably 2 to 4, and Y may be the same or different and is optionally selected from -O-, -NH-, -C(O)-, -C(S)-, and [ka] and one or more groups selected from the group consisting of a carboxyl (-COOH) group, a carboxylate anion (-COO - ) groups and hydroxyl groups, optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals having up to 1005 carbon atoms, which may be substituted by one or more substituents selected from with the proviso that at least one of the radicals Y is of formula (VIII) or (VIII * ) -R 8 (-C(O)-XR 8 ) m -C(O)-XR 9 (VIII) -R 8 (-C(O)-XR 8 ) m -C(O)-XR 9* (VIII * ) In the formula (VIII), X, m and R 8 , and R 9 are each as defined above for formula (VI), and Formula (VIII * ) in X, m, and R 8 , and R 9* are represented by the formula (VI * ) is as defined above; In addition, R in formula (VII) 7 and at least one of Y is one or more carboxylate anions (-COO- ) group, Formula (X): R 7 (-C(O)-XR 8 -COO - ) q Here, X and R in formula (X) 7 , R 8 , and q are as defined above for formulas (VII) and (VIII), respectively.

[0019] According to the invention, estolides are natural and synthetic compounds, in particular derived from fats and oils, and more particularly derived from fatty acid compounds that are typically obtainable by hydrolysis of fats and oils.

[0020] The estolide structure is distinguished by a secondary ester bond from one fatty acyl molecule to the alkyl backbone of the other fatty acid fragment. The terms "fatty acid" and "fatty acyl molecule" may seem to suggest that the individual residues must be derived from fatty components, but this is not the case. The term "fatty acid" in this application refers to a carboxylic acid with a chain-like organyl group, and in particular to unbranched aliphatic monocarboxylic acids. Fatty acids are distinguished from one another by the number of carbon atoms (chain length) and, for unsaturated fatty acids, by the number and position of double bonds. Fatty acids may be distinguished as short-chain fatty acids of up to 7 carbon atoms, medium-chain fatty acids of 8 to 12 carbon atoms, long-chain fatty acids of 13 to 21 carbon atoms, and very long-chain fatty acids of more than 22 carbon atoms.

[0021] In accordance with the present invention, the group "-O-" generally represents an ether group, which also includes the presence of an epoxide moiety which is a three-membered ether group. Thus, optionally, the groups defined above as including the group "-O-" may include an epoxy group.

[0022] In general, the features of all embodiments according to the invention described below can be freely combined unless otherwise stated or unless a combination of features or the incorporation of independent features of one embodiment in another embodiment is parametrically impossible, i.e. they are logically incompatible.

[0023] According to the present invention, an organoammonium group is any group that contains a quaternary nitrogen atom and that is bonded directly to at least one carbon atom of an organyl group, i.e., to at least one carbon atom of any organic substituent, regardless of the type of functional group, that has a free valence on that carbon atom.

[0024] In accordance with the present invention, the organic ammonium salt cation, or the organic ammonium cations if the salt contains more than one, does not contain a moiety of formula (III) or (IV): (-ZC(O)-R 6 ) r -ZC(O)- (III) or (-C(O)-ZR 6 ) r -C(O)-Z- (IV).

[0025] base R 6 may be identical or different and are selected from optionally substituted linear, cyclic or branched, substituted or unsubstituted hydrocarbon radicals having from 1 to 36 carbon atoms and thus may represent hydrocarbyl groups 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 alkarylene groups, linear, branched or cyclic aralkylene groups and linear, branched or cyclic arylene groups, such as phenylene, benzylene or tolylene groups, in particular from such groups having from 1 to 22 carbon atoms.

[0026] At which carbon atom of the hydrocarbyl radical are the adjacent groups C(O) and Z groups R 6There are no restrictions as to which

[0027] Z may be the same or different and is O or NR 11 is selected from, where R 11 are independently hydrogen, or optionally -O-, -NH-, -C(O)-, -C(S)-, [ka] and optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals having up to 100 carbon atoms, which contain one or more groups selected from the group consisting of:

[0028] R of the moiety defined by formula (III) or formula (IV) excluded from the cationic structure 6 Repeating unit (-ZC(O)-R 6 ) or (-C(O)-ZR 6 The number of anions (COO) is from 1 to 20. The organic ammonium salt according to the present invention comprises at least one carboxylate anion (COO) selected from the group consisting of the anions of formulae (V), (VII) and (X) defined above. - ) group-containing anions.

[0029] The structure of the anion of formula (V) is defined as follows: R 7 (-XC(O)-G) p (V)

[0030] According to the invention, in formula (V) the residue R 7 is a valence p, where p is ≧1 to 811, preferably 2 to 811, even more preferably 2 to 100, more preferably 2 to 50, even more preferably p is 2 to 30, or 3 to 25, or 4 to 20, which is the residue R 7carries p residues of the structure (-XC(O)-G), where G is as defined below. Thus, the term "p-valent" refers to the number of residues R 7 It does not refer to or limit the number of optional further substituents, which may be carboxyl, carboxylate or hydroxyl groups, other than (-XC(O)-G).

[0031] According to the present invention, the phrase "optionally substituted hydrocarbon radical", which may optionally contain and be substituted by one or more specified functional groups, refers to an organyl radical linked through at least one of its carbon atoms to one or more further groups, where the hydrocarbyl structure of the radical may be interrupted by the specified functional groups defined to be contained, and where one or more hydrogen atoms of the hydrocarbyl group can be replaced by a substituent as indicated.

[0032] For example, R 7 In the case of , one or more hydrogen atoms may be replaced by a hydroxyl group, a carboxyl group, or a carboxylate group.

[0033] Additionally, optionally substituted hydrocarbon radicals R 7 is specifically -O-, -NH-, -C(O)-, -C(S)- and [ka] Thus, R 7 The hydrocarbyl structure of the radical may be interrupted by these groups or combinations thereof.Thus, the residue may include ester groups, carboxyl groups, amide groups, ether groups, amino groups, carbonyl groups, thione groups, thiocarboxylate groups, thioester groups, carbamate groups, urethane groups, epoxide groups, and all other groups specified for this radical, and combinations thereof.

[0034] R is p-valent with respect to the residue (-XC(O)-G) in formula (V). 7 The hydrocarbyl structure is 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 alkarylene groups, linear, branched or cyclic aralkylene groups and linear, branched or cyclic arylene groups, such as phenylene, benzylene or tolylene groups, especially those groups having from 1 to 1000 carbon atoms, more especially from 1 to 150 carbon atoms.

[0035] Preferably, the hydrocarbon structure is a linear or branched alkylene group or a linear or branched alkylene group interrupted by an ether group, an ester group or both an ether group and an ester group, in particular a branched structure derived from a product obtained by esterifying a polyol with a mono- or polyhydroxycarboxylic acid having up to 150 carbon atoms or with a linear alkylene group having up to 22 carbon atoms.

[0036] More preferably, the p-valent R of formula (V) 7 The radicals are selected from alkylene groups, which may be selected from the group consisting of linear, branched and cyclic alkylene groups, in particular linear C1-C22 alkyl groups such as methylene, ethylene, n-propylene, n-butylene, n-pentylene, n-hexylene, n-heptylene or n-octylene groups, branched C1-C22 alkylene groups such as isopropylene, isobutylene, tert-butylene, isobutylene, tert-pentylene, neopentylene and 2-ethylhexylene groups.

[0037] Which carbon atom in the hydrocarbyl radical is R 7 There is no restriction as to whether the aryl group bears one or more (-XC(O)-G) groups attached to the aryl group.

[0038] R 7Regarding the presence of functional groups and optional substituents optionally contained in R 7 is derived from glycidyl compounds, glycerin and glycerin derivatives, in particular glycidol, glycerin diglycidyl ether, diglycidyl ethers and polyglycerin compounds, or R 7 is preferably a straight-chain alkylene group, in particular an alkylene group which carries no further substituents in addition to the (-XC(O)-G) group, and even more preferably R 7 are derived from the condensation products of glycidol, glycerin, glycerin diglycidyl ether, diglycidyl ether and polyglycerol compounds with C8-C24 monohydroxy fatty acids, in particular ricinoleic acid, lesquerolic acid or 12-hydroxystearic acid.

[0039] R 7 is a dendrimer structure, it preferably comprises monocarboxylic acids having 2 to 6 hydroxy groups, of which at least one, preferably all hydroxyl groups are esterified with a monocarboxylic acid carrying 2 to 6 hydroxy groups. Optionally, one, two or more branching cycles may be performed, in which a further monocarboxylic acid carrying 2 to 6 hydroxy groups is added via esterification of the hydroxyl groups of the monocarboxylic acid applied in the previous branching cycle.

[0040] It is also preferred that the monocarboxylic acids having 2 to 6 hydroxy groups of subsequent branching cycles are interconnected by estolide chains.

[0041] R 7 When includes a dendrimeric structure, it is generally preferred to use one type of monocarboxylic acid having from 2 to 6 hydroxy groups, such as 2,2-bis-(hydroxymethyl)propionic acid, to provide a branched structure.

[0042] These R 7 An example of this is: [ka] where [ka] [ka]

[0043] As will be appreciated by those skilled in the art, the group (-XC(O)-G) is typically represented by the radical R 7 via the -XC(O)- unit, and in particular via the -OC(O)- unit, R 7 In the compound from which it is derived, -OH or -NHR 11 The group is attached at the position where it was previously substituted.

[0044] For example, R derived from glycerin 7 The group is a 1,2,3-propylene radical, where "1,2,3" indicates the positions at which this radical is substituted by the (-XC(O)-G)- groups.

[0045] According to the present invention, the term "optionally substituted hydrocarbon residue" does not impose any further restrictions on the radicals, and therefore they are defined as follows: the groups that may optionally be contained or present as substituents, the number of carbon atoms of the specified residue, and whether they are represented by formula (V), formula (VI), formula (VI * ) and formula (VII), formula (VIII), formula (VIII * ), is defined by the way in which it is attached to other structural moieties of the compounds according to the invention as defined by formula (X) or any additional formula used to define an embodiment according to the invention.

[0046] According to the invention, the groups X may be the same or different and are -O- or -NR 11 - selected from, where R 11 is hydrogen, or optionally -O-, -NH-, -C(O)-, -C(S)-, [ka] or a group consisting of optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals having up to 100 carbon atoms containing one or more groups selected from the formula (V)R 11 In R 7 The bond to the ring often forms a ring structure.

[0047] R 11 Preferred examples of are C1-C10 alkyl groups, especially methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentane and n-hexane groups, cyclopentyl and cyclohexane groups, C2-C10 alkenyl groups, especially vinyl and allyl groups, and C6-C12 aromatic groups, especially phenyl, tolyl and benzyl groups, each of which may be substituted by a hydroxyl or halide group.

[0048] According to the invention, the residues G may be identical or different and are optionally -O-, -NH-, -C(O)-, -C(S)-, [ka] and optionally substituted by one or more groups selected from carboxyl, hydroxyl or halide groups, optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals having up to 1005 carbon atoms, with the proviso that at least one compound of radical G has the formula (VI) or (VI * ) -R 8 (-XC(O)-R 8 ) m -XC(O)-R 9 (VI) -R 8 (-XC(O)-R 8) m -XC(O)-R 9* (VI * ) In the formula, X is as defined above. m=0 to 20, preferably 1 to 20; R 8 are independently selected from optionally substituted, linear, cyclic, or branched, substituted or unsubstituted divalent hydrocarbon radicals having up to 36 carbon atoms; R 9 is optionally -O-, -NH-, -C(O)-, -C(S)-, [ka] and one or more groups selected from the group consisting of a carboxyl (-COOH) group, a carboxylate anion (-COO - ) groups, hydroxyl (-OH) groups, and halide (-halogen) groups, optionally substituted linear, cyclic, or branched, substituted or unsubstituted hydrocarbon radicals having from 1 to 1000 carbon atoms, which may be substituted with one or more groups selected from the radical R 9 is the internal carboxy (-COO - ) group or (-CON(R')-, where R' is hydrogen or an organic group) amide group, i.e., R 9 cannot contain a combination of -C(O)- and -O- groups or a combination of -C(O)- and -NH- or tertiary amino groups; and However, formula (VI)R 9 in at least one moiety of formula (VI) having at least 2, preferably at least 6, carbon atoms, and in the same moiety of formula (VI) R 8 at least one of has at least 6, preferably at least 8, carbon atoms; R 9* is optionally -O-, -NH-, -C(O)-, -C(S)-, [ka] and optionally substituted branched or dendrimeric hydrocarbon radicals having from 1 to 1000 carbon atoms, which may be substituted with carboxyl, hydroxyl, or halide groups, where the radical R 9* is terminated by two or more groups of the general structure -XC(O)-T where X is as defined above, and T is a monovalent linear, cyclic, or branched, substituted or unsubstituted hydrocarbon radical of up to 36 hydrocarbons optionally substituted with carboxyl, hydroxyl, or halide groups; However, formula (VI * )R 9* is terminated by one or more groups T having at least 2, preferably at least 6, carbon atoms, and is represented by the formula (VI * ) in the same component of R 8 At least one of has at least 6, preferably at least 8 carbon atoms.

[0049] According to the present invention, R 7 and at least one of G is one or more carboxylate anions (-COO - ) group.

[0050] Preferably, the group G consists solely of groups of formula (VI) or the group G consists solely of groups of formula (VI * ) groups.

[0051] According to the present invention, R 8 is independently selected from optionally substituted linear, cyclic, or branched, substituted or unsubstituted divalent hydrocarbon radicals having up to 36 carbon atoms. Thus, it may be an optionally substituted linear, cyclic, or branched, saturated, unsaturated, or aromatic divalent hydrocarbon radical, i.e., R 8may represent a hydrocarbyl group 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 alkarylene groups, linear, branched or cyclic aralkylene groups and linear, branched or cyclic arylene groups, such as phenylene, benzylene or tolylene groups, in particular such groups having from 1 to 24 carbon atoms, each optionally containing one or more hydroxyl groups.

[0052] More preferably, R 8 The radicals are selected from linear alkylene and alkenylene groups, in particular linear C6-C24 alkylenes such as hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, doicosylene, tricosylene, and tetraicosylene; and selected from linear C6-C24 alkenylene groups such as butenylene, nonenylene, decenylene, undecenylene, dodecenylene, tridecenylene, tetradecenylene, pentadecenylene, hexadecenylene, heptadecenylene, octadecenylene, nonadecenylene, eicosenylene, henicosenylene, doicosenylene, tricosenylene, and tetraicosenylene, where the groups are most preferably linked by a terminal carbon atom to the adjacent C(O) group.

[0053] At which carbon atom of the hydrocarbyl radical are adjacent groups C(O) and X groups R 8 However, there are no restrictions on what R 8 is preferably derived from a hydroxycarboxylic acid bearing one or more hydroxyl groups, more preferably from a monohydroxycarboxylic acid, most preferably from a C7-C25 fatty acid bearing one hydroxyl group as a substituent. Thus, R 8preferably represents the alkylene or alkenylene chain of such a carboxylic acid. For example, R 8 is derived from ricinoleic acid, [ka] R 8 represents the 1,11-heptadec-8-enyl radical, [ka] In the formula, "1,11" indicates the positions at which this radical is attached to the adjacent groups X and C(O).

[0054] R 8 Preferred examples for R are structures derived by abstraction of a carboxylate group and one OH group from the corresponding hydroxyl carboxylic acid, where the hydroxyl carboxylic acid is preferably selected from ricinoleic acid, lesquerolic acid, 10-hydroxyoctadecanoic acid, 12-hydroxyoctadecanoic acid, 14-hydroxytetradecanoic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or dihydroxycarboxylic acids, in particular 2,2'-dihydroxymethylpropanoic acid, 9,10-dihydroxystearic acid, or polyhydroxycarboxylic acids, in particular gluconic acid. Most preferably, R 8 are derived from lesquerolic acid or ricinoleic acid in the manner described above. In each case, the naturally occurring enantiomeric compounds are particularly preferred, namely (9Z,12R)-12-hydroxyoctadec-9-enoic acid, obtained by saponification or fractional distillation of the hydrolysis of castor oil, the seed oil of the castor plant, and (11Z,14R)-14-hydroxyicos-11-enoic acid, isolated from the seeds of Pisonia and Physalia. However, according to the invention, the racemates, S enantiomers and E configuration isomers of these compounds, their racemates, enantiomers and any possible mixtures are also preferred.

[0055] At least one moiety R present in the group G of the compound of general formula (V)8 Repeating unit (-XC(O)-R 8 ) is from 0 to 20, preferably from 0 to 15, from 0 to 12, from 0 to 10, from 0 to 8, or from 1 to 20, from 2 to 20, from 3 to 20, from 4 to 20, from 5 to 20, in particular from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0056] R 9 is optionally -O-, -NH-, -C(O)-, -C(S)-, [ka] and one or more groups selected from the group consisting of a carboxyl (-COOH) group, a carboxylate anion (-COO - ) groups, hydroxyl (-OH) groups, and halide (-halogen) groups, optionally substituted linear, cyclic, or branched, substituted or unsubstituted hydrocarbon radicals having from 1 to 1000 carbon atoms, which may be substituted with one or more substituents selected from the radical R 9 is the internal carboxy (-COO - ) group or (-CON(R')-, where R' is hydrogen or an organic group) amide group, i.e., R 9 cannot contain a combination of -C(O)- groups with -O- groups or a combination of -C(O)- groups with -NH- or tertiary amino groups.

[0057] According to the invention, the radical R 9may be identical or different and may represent a hydrocarbyl group selected from optionally substituted, linear, cyclic or branched, substituted or unsubstituted, hydrocarbon radicals having from 1 to 36 carbon atoms, and thus 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 alkaryl groups, linear, branched or cyclic aralkyl groups, and linear, branched or cyclic aryl groups, such as phenyl groups, benzyl groups or tolyl groups, in particular having from 6 to 24 carbon atoms, each optionally containing one or more functional groups as described above.

[0058] More preferably, R 9 The radicals are straight chain alkyl and alkenyl groups, in particular straight chain C6-C24 alkyl groups such as 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, It is selected from linear C6-C24 alkenyl groups such as decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl, henicosenyl, doicosenyl, tricosenyl, and tetraicosenyl, where these groups are most preferably bonded to the adjacent C(O) or X group via a terminal C atom.

[0059] At which C atom of a hydrocarbyl radical is the adjacent C(O) group R 9 There are no restrictions on which

[0060] However, R 9is preferably derived from a carboxylic acid or a hydroxycarboxylic acid bearing one or more hydroxyl groups, more preferably from a carboxylic acid or a monohydroxycarboxylic acid, and most preferably from a C7-C25 fatty acid bearing no hydroxyl groups as substituents. Thus, R 9 preferably represents the alkyl or alkenyl chain of such a carboxylic acid. For example, R 9 is derived from oleic acid, [ka] At that time R 9 represents the heptadec-8-enyl radical [ka]

[0061] R 9 Preferred examples for are structures derived by abstraction of a carboxylate group from the corresponding carboxylic or hydroxyl carboxylic acid, where the carboxylic acid is acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic 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, γ-linolenic acid, nonadecylic acid, arachidic acid, mead acid, arachidonic acid, heneicosapentaenoic acid, benzo ... The hydroxycarboxylic acids may be selected from hydroxycarboxylic acids, such as oleic acid, ricinoleic acid, 10-hydroxyoctadecanoic acid, 12-hydroxyoctadecanoic acid, 14-hydroxytetradecanoic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or from dihydroxycarboxylic acids, in particular 2,2'-dihydroxymethylpropanoic acid, 9,10-dihydroxystearic acid, or from polyhydroxycarboxylic acids, in particular gluconic acid.

[0062] Radical R 9is optionally -O-, -NH-, -C(O)-, -C(S)-, [ka] and may be substituted with OH or halide groups, but may not include the radical R 9 cannot contain a combination of -C(O)- groups with -O- groups, or a combination of -C(O)- groups with -NH- or tertiary amino groups to form an internal carboxylate group, i.e., an internal ester group, or an internal amide group.

[0063] According to the present invention, in at least one portion of formula (VI), R 9 contains at least 2, preferably at least 6, carbon atoms, and at least one R 8 It is necessary that the alkyl group has at least 6, preferably at least 8, carbon atoms.

[0064] As mentioned above, according to the present invention, R 9* is defined as a monovalent radical, resulting in the structural feature of being terminated by at least two groups of the general formula: -XC(O)-T residue R 9* In the above, the presence of at least one branched structure is essential.

[0065] R 9* When is a branched hydrocarbon radical, this group contains as a branched structure at least one moiety of the general formula: -B(-O-) b where B is a straight or branched chain hydrocarbon radical having 3-20 carbon atoms, preferably 3-10 carbon atoms, more preferably B is an alkyl radical having 3-10 carbon atoms, and b is 2 or greater, preferably 2-6, more preferably 2-4, and where the group (-O-) is linked on one side to the group B and on the other side to a carbon atom, where the carbon atom is CH 2It may be the C atom of a group or a carbonyl group.

[0066] R 9* When is a dendrimeric hydrocarbon radical, it comprises at least one moiety of the general formula: -B(-O-) b where B and b are as defined above, and the group (-O-) is linked on one side to the group B and on the other side to a carbon atom; and is linked to at least one further moiety of the following general formula, which acts as a branching structure: -C(O)-B(-O-) b wherein B and b are as defined above, and the group (-O-) is linked on one side to the group B and on the other side to a carbon atom, where the carbon atom is CH 2 It may be a C atom of a group or a carbonyl group. The term dendrimeric hydrocarbon structure thus refers to a branched structure comprising at least two consecutive branched structures.

[0067] base R 9* may also comprise two or more branched structures linked by an estolide chain structure, i.e. the two or more branched structures are linked by a linear hydrocarbon chain containing at least two internal ester groups, preferably a linear hydrocarbon chain obtained by esterification of two or more C2-C24 hydroxycarboxylic acids.

[0068] Each of the groups T is R 9* It constitutes one of at least two terminal groups of the group and is typically derived from a fatty acid. Thus, the group T is preferably a straight-chain saturated or monounsaturated hydrocarbon radical having from 2 to 24 carbon atoms.

[0069] The group T preferably has the general formula -B(-O-) b or -C(O)-B(-O-) b It is linked to the (-O-) group of the branched structure via a carbonyl group or an estolido chain.

[0070] Due to the presence of the branched structure mentioned above, R 9* has a branched structure, and even a dendrimer structure.

[0071] The following structure is R 9* is an example of a branched hydrocarbon radical as shown above: [ka]

[0072] Wherein the general formula B(-O-) b is derived from 2,2'-dihydroxymethylpropionic acid, and the group T is an n-heptadecanyl group linked to the branched structure. It is derived from stearic acid and is linked to the group B by a -C(O)-O- unit. Thus, this structure is terminated by two groups of the general structure -X-(CO)-T, and has the formula -B(-O-) 2 It contains a branched structure.

[0073] Branching group R 9* Examples of groups from which may be derived are shown below: [ka] Where R = [ka]

[0074] The corresponding group R 9* In the previous structure, the branched structure is the same as in the previous structure, but the two terminal groups T, which are n-heptadec-9-enyl groups derived from oleic acid, are attached to the branched structure via estolide chain structures derived from ricinoleic acid.

[0075] The group R according to the present invention 9* Another example of a dendrimer hydrocarbon is shown below:

[0076] Therein, the branched structure -B(-O-) b has two further branched structures -(C(O)-B(-O-) b follows directly, resulting in further augmentation of the end groups of the general structure -XC(O)-T: [ka]

[0077] Therein, the branched structure is derived from 2,2'-dihydroxymethylpropionic acid and the end groups are based on stearic acid.

[0078] Branched or dendrimer group R 9* It is also within the scope of the invention as defined above that the terminal group -XC(O)-T is not directly linked to the group B of the branched structure, but is linked to the (-O-) group of the branched structure by a hydrocarbon group such as an optionally substituted or heteroatom-containing alkylene or alkenylene, preferably an n-alkylene having 2 to 10 carbon atoms, a poly(alkylene oxide) group such as a poly(ethylene oxide) or poly(propylene oxide) group, or in particular an oligoester or polyester group, i.e. an estolido chain.

[0079] In the following example, the stearic acid based group -XC(O)-T is linked by an estolide chain to the branched structure: [ka] where [ka]

[0080] As already mentioned above, the dendrimer group R 9* In the structure -(C(O)-B(-O-) b One or more branching elements of the structure -B(-O-) bor -(C(O)-B(-O-) b It is likewise within the scope of the invention as defined above that the branching elements are not directly linked to the above branching elements, but are linked by a hydrocarbon group such as an optionally substituted or heteroatom-containing alkylene or alkenylene, preferably an n-alkylene having 2 to 10 carbon atoms, a poly(alkylene oxide) group such as a poly(ethylene oxide) or poly(propylene oxide) group, or in particular an oligoester or polyester group, i.e. an estolide chain.

[0081] In the following example, the branched structures are linked by estolide chains: [ka] where [ka]

[0082] Furthermore, the carboxylate anion (COO - ) groups in anions 7 and at least one of G is one or more carboxylate anions (-COO - ) group, preferably one, two or three carboxylate groups.

[0083] The structure of the anion of formula (VII) is defined as follows: R 7 (-C(O)-XY) q (VII) R 7 and X in formula (VII) is R 7 is as defined above for formula (V), except that R is q-valent with respect to the residue (-C(O)-XY). 7 and all the options given as being preferred for X are R 7 and similarly preferred for X.

[0084] Y may be the same or different and is optionally selected from -O-, -NH-, -C(O)-, -C(S)-, and [ka] and one or more groups selected from the group consisting of a carboxyl (-COOH) group, a carboxylate anion (-COO - ) groups and hydroxyl groups, optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals having up to 1005 carbon atoms, which may be substituted by one or more substituents selected from with the proviso that at least one of the radicals Y is of formula (VIII) or (VIII * ) -R 8 (-C(O)-XR 8 ) m -C(O)-XR 9 (VIII) -R 8 (-C(O)-XR 8 ) m -C(O)-XR 9* (VIII * ) In the formula (VIII), X, m and R 8 , and R 9 are each as defined above for formula (VI), and Formula (VIII * ) in X, m, and R 8 , and R 9* are represented by the formula (VI * ) is as defined above.

[0085] Preferably, the group Y consists solely of a group of formula (VIII) or of formula (VIII * ) groups.

[0086] More preferably, the formula (VIII) and (VIII * ) at least one R 8The minimum chain length of formula (VIII) is 8 carbon atoms, and more preferably formula (VIII) * ) all groups R 8 The chain length of is at least 8 carbon atoms and also preferably has the formula (VIII) and (VIII * ) at least one R 9 The minimum chain length of the anion of the organic ammonium salt is 8 carbon atoms, and more preferably the anion of the organic ammonium salt has the formula (VIII) and (VIII * ) all groups R 9 The chain length is at least 8 carbon atoms.

[0087] R in formula (VII) 7 and at least one of Y is one or more, preferably one or two or three, carboxylate anions (-COO - ) group.

[0088] In the anion of formula (VII), q is from 1 to 55, preferably from 1 to 40, more preferably from 2 to 25, even more preferably from 2 to 15, and most preferably from 2 to 4.

[0089] The structure of the anion of formula (X) is defined below: R 7 (-C(O)-XR 8 -COO - ) q (X) R 7 and X in formula (X) is R 7 is the residue (-C(O)-XR 8 -COO - As defined above for formula (VII), except that R is q-valent; 8 and q is as defined above in formula (VIII). Preferably, q is in the range of 1-3, in particular 1, 2 or 3.

[0090] According to formulas (V) and (VII) and the groups contained in these structures, the anion of the organic ammonium salts of the present invention is represented by the central moiety R 7and they may include a branched structure or a dendrimer branched structure in the formula (VI * ) and (VIII * ) group R 9* It is understood that R may contain a branched structure at an internal position or adjacent to a terminal group. In general, it is within the scope of the present invention for only the groups Y and G to contain branched structures, so long as the condition regarding the presence of an estolide moiety is met, and R 7 and both G and R 7 It is also within the scope of the present invention that both and Y include branched structures.

[0091] In a preferred embodiment of the invention, the organoammonium group-containing cation of the organoammonium salt according to the invention is selected from the cations of formula (I): R 1 (-F) x (I) During the ceremony x is 1 to 50, preferably 2 to 50; R 1 is selected from optionally substituted x-valent hydrocarbon radicals having up to 1000 carbon atoms, preferably from 2 to 300 carbon atoms, more preferably from 3 to 200 carbon atoms, even more preferably from 3 to 150 carbon atoms, particularly from 3 to 50 carbon atoms, and more particularly from 3 to 20 carbon atoms, and optionally selected from -O-, -NH-, -C(O)-, -C(S)-, [ka] and R 1 is a carboxyl (-COOH) group, a carboxylate anion (-COO - ) groups, hydroxyl (-OH) groups, and halide (-halogen) groups; and F may be the same or different and is represented by the following general formula (II): [ka] where the group F is R 1 is attached to a carbon atom of n is independently 0 to 1000; R 2 may be the same or different and may optionally be -O-, -NH-, -C(O)-, -C(S)-, [ka] and optionally substituted divalent hydrocarbon radicals having up to 1000 carbon atoms, including one or more groups selected from 2 can be substituted with one or more groups selected from OH groups and halide groups, and R 3 , R 4 , R 5 may be the same or different and are hydrogen and optionally -O-, -NH-, -C(O)-, -C(S)-, [ka] and optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals having up to 1000 carbon atoms containing one or more groups selected from: Here, R 3 , R 4 , R 5 are bonded to the nitrogen atom through a carbon atom if they are not hydrogen.

[0092] According to the invention, the residue R 1 is x-valent, where x is from 1 to 50, preferably from 2 to 50, which means that the residue R 1 carries x number of residues F as defined by the general formula (II). Thus, the term "x-valent" refers to the number of residues R, which may be hydroxyl and halide groups. 1 It is not intended to indicative or limit the number of optional further substituents other than F.

[0093] R 1 In the formula (I), one or more hydrogen atoms may be replaced by a hydroxyl group or a halide substituent, ie, a fluorine, chlorine, bromine or iodine substituent.

[0094] Additionally, optionally substituted hydrocarbon radicals R 1 is specifically -O-, -NH-, -C(O)-, -C(S)- and [ka] Thus, R 1 The hydrocarbyl structure of the radical may be interrupted by these groups or combinations thereof. Thus, the residue may include ester groups, carboxyl groups, amide groups, ether groups, amino groups, carbonyl groups, thione groups, thiocarboxylate groups, thioester groups, carbamate groups, urethane groups, epoxide groups and all other groups specified for this radical, as well as combinations thereof. The same principle applies to optionally substituted hydrocarbon radicals R 2 , R 3 , R 4 , R 5 However, the above groups are not combined in such a way that a moiety of formula (III) or (IV) as defined above is formed.

[0095] R that is x-valent with respect to 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 alkynyl or alkynylene groups, linear, branched or cyclic alkaryl or alkarylene groups, linear, branched or cyclic aralkyl or aralkylene groups, and linear, branched or cyclic aryl or arylene groups, such as phenyl or phenylene groups, benzyl or benzylene groups, or tolyl or tolylene groups, especially those groups having 1 to 30 carbon atoms.

[0096] More preferably, x-valent R 1 The radicals are selected from alkyl or alkylene groups, which may be selected from the group consisting of linear, branched and cyclic alkyl or alkylene groups, or combinations of linear and cyclic alkyl or alkylene structures, or combinations of branched and cyclic structures, in particular linear C1-C22 alkyl and alkylene 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, isopropyl groups. and isopropylene, isobutyl, isobutylene, tert-butyl, isopentyl, isobutylene, tert-pentyl, tert-pentylene, neopentyl, and neopentylene, and 2-ethylhexyl, and 2-ethylhexylene; and cyclic C3-C22 alkyl and alkylene groups, such as cyclopropyl and cyclopropylene, cyclobutyl and cyclobutylene, cyclopentyl and cyclopentylene, cyclohexyl and cyclohexylene, and cycloheptyl and cycloheptylene.

[0097] When x>1, at which carbon atom of the hydrocarbyl radical is a group F R 1There are no restrictions on what is bound to R 1 Regarding the presence of functional groups and optional substituents optionally contained in R 1 is preferably derived from glycidyl compounds, glycerin and glycerin derivatives, in particular glycidol, glycerin, glycerin diglycidyl ether, diglycidyl ethers and polyglycerin compounds, or R 1 It is preferred that is a straight-chain alkylene group, in particular an alkylene group which carries no further substituents in addition to the group F.

[0098] According to the present invention, R 1 It is particularly preferred that R is derived from glycerol diglycidyl ether, which is 2 is formed by opening the epoxide ring of glycerol diglycidyl ether with a nitrogen atom, and then the quaternary N atom is attached to R 1 It means that the R 1 is preferably derived from diglycidyl ethers, diglycerol diglycidyl ether, triglycerol diglycidyl ether, polyglycerol terminated with glycidyl units, and poly(alkylene oxide) compounds terminated with glycidyl units, in particular poly(ethylene oxide) terminated with glycidyl units, poly(propylene oxide) terminated with glycidyl units, and poly(butylene oxide) terminated with glycidyl units.

[0099] Also R 1 It is also preferred that R is formed from a compound obtained by esterification of a polyol, in particular a diol compound such as an α,ω-diol or an α,ω-dihydroxy polyether, more particularly a dihydroxy-terminated poly(ethylene oxide), dihydroxy-terminated poly(propylene oxide) or dihydroxy-terminated poly(butylene oxide), with an ω-halocarboxylic acid, in particular ω-chloroacetic acid or ω-chloropropanoic acid. 1 R is formed by replacing the chlorine substituent with the nitrogen atom of group F adjacent to the group 1 Form.

[0100] According to this, R 1 is preferably a C3-C50 alkylene group containing one or more internal ether or ester groups, and R 1 It is particularly preferred that is an alkylene group bearing a hydroxyl substituent.

[0101] R 1 is a straight-chain C1-C8 alkylene group having no further substituents or functional groups, or R 2 It is most preferred that is a linear C3 to C50 alkylene group derived from diglycidyl ether, glycerin diglycidyl ether, diglycerin diglycidyl ether, diethylene glycol diglycidyl ether, or ethylene glycol diglycidyl ether having from 3 to 10 (ethylene oxide) repeat units.

[0102] residue R 2 , R 3 , R 4 , and R 5 can be an optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radical, where R 2 represents a divalent radical, whereas R 3 , R 4 and R 5 is a monovalent radical. R 2 The term "divalent" is R 2 is attached to two quaternary nitrogen atoms according to formula (II), but R 2 This does not limit the presence of additional substituents as defined for.

[0103] Radical R 3 , R 4 and R 5are monovalent radicals, which may be identical or different, selected from hydrogen and optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals having up to 1000 carbon atoms, and thus may represent linear, i.e. straight-chain, cyclic or branched alkyl groups, linear, cyclic or branched alkenyl groups, linear, cyclic or branched alkynyl groups, linear, cyclic or branched alkaryl groups, linear, cyclic or branched aralkyl groups, and aryl groups, such as phenyl, benzyl or tolyl groups, in particular groups having from 1 to 30 carbon atoms, and optionally substituted by OH or halide groups, and optionally -O-, -NH-, -C(O)-, -C(S ... [ka] According to the invention, the above groups contain one or more groups selected from the group R 1 , R 2 , R 3 , R 4 and R 5 are not combined in such a way that there is a moiety of formula (III) or (IV) as defined above in either of the

[0104] Preferably, the radical R 3 , R 4 , and R 5is selected from alkyl groups, which may be selected from the group consisting of linear, branched and cyclic alkyl groups, or a combination of linear and cyclic alkyl structures, or a combination of branched and cyclic structures, in particular from linear C1-C22 alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl or n-octyl, branched C1-C22 alkyl groups such as isopropyl, isobutyl, tert-butyl, isopentyl, tert-pentyl, neopentyl and 2-ethylhexyl, and cyclic C3-C22 alkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl, more preferably from the radical R 3 , R 4 , and R 5 is selected from methyl, ethyl, isopropyl, tert-butyl, cyclopentyl or cyclohexyl, most preferably methyl.

[0105] The radical R according to the present invention 2 may be the same or different and are optionally -O-, -NH-, -C(O)-, -C(S)-, [ka] and optionally substituted divalent hydrocarbon radicals having up to 1000 carbon atoms, which contain one or more groups 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 alkarylene groups, linear, branched or cyclic aralkylene groups, and linear, branched or cyclic arylene groups, such as phenylene groups, benzylene groups or tolylene groups, in particular those of this group having 1 to 100 carbon atoms, each optionally containing one or more functional groups as defined above.

[0106] More preferably, R 2 The radicals are selected from alkylene groups, It may be selected from the group consisting of linear, branched and cyclic alkylene groups, or combinations of linear and cyclic alkylene structures, or combinations of branched and cyclic structures, in particular from linear C1-C50 alkylene groups such as methylene, ethylene, n-propylene, n-butylene, n-pentylene, n-hexylene, n-heptylene or n-octylene, branched C4-C50 alkylene groups such as isopropylene, isobutylene, tert-butylene, tert-pentylene, neopentylene and 2-ethylhexylene, and cyclic C3-C22 alkylene groups such as cyclopropylene, cyclobutylene, cyclopentylene, cyclohexylene and cycloheptylene.

[0107] At which carbon atom of the hydrocarbyl radical is a quaternary nitrogen atom R 2 There are no restrictions on which

[0108] In accordance with the present invention, n is independently 0-1000, preferably 0 to 500, more preferably 0-250, even more preferably 0-50, and even more preferably 0-25 or 0-10. Also preferred is that n is at least 1, 2, 3, 4, 5, 6, 7, 8 or 9.

[0109] R 2 Regarding the presence of functional groups and optional substituents optionally contained in R 2 is preferably derived from glycidyl compounds, glycerin and glycerin derivatives, in particular glycidol, glycerin diglycidyl ether, diglycidyl ethers and polyglycerin compounds, or R 2 It is preferred that is a straight chain alkylene group, in particular an alkylene group which carries no further substituents in addition to the quaternary nitrogen atom.

[0110] As mentioned above, R2 It is particularly preferred that R is derived from glycerol diglycidyl ether, which is 2 is formed by opening the epoxide ring of glycerol diglycidyl ether with a nitrogen atom, and then the quaternary N atom is attached to R 2 It means that the R 2 is preferably derived from diglycidyl ether, diglycerol diglycidyl ether, triglycerol diglycidyl ether, polyglycerol terminated with glycidyl units, and poly(alkylene oxide) compounds terminated with glycidyl units, in particular poly(ethylene oxide) terminated with glycidyl units, poly(propylene oxide) terminated with glycidyl units, and poly(butylene oxide) terminated with glycidyl units. 2 It is also preferred that R is formed from a compound obtained by esterification of an α,ω-diol or a diol compound such as an α,ω-dihydroxy polyether, more particularly a dihydroxy-terminated poly(ethylene oxide), a dihydroxy-terminated poly(propylene oxide), or a dihydroxy-terminated poly(butylene oxide), with an ω-halocarboxylic acid, in particular ω-chloroacetic acid or ω-chloropropanoic acid. 2 The R group is formed by replacing the chlorine substituent with a nitrogen atom adjacent to the R group. 2 Form.

[0111] According to the present invention, R 2 is preferably a C3-C50 alkylene group containing one or more internal ether or ester groups, and R 2 It is particularly preferred that is such an alkylene group bearing a hydroxyl substituent.

[0112] R 2 is a linear C1-C8 alkylene group having no further substituents or functional groups, or R 2It is most preferred that is a linear C3 to C50 alkylene group derived from diglycidyl ether, glycerin diglycidyl ether, diglycerin diglycidyl ether, diethylene glycol diglycidyl ether, or ethylene glycol diglycidyl ether having from 3 to 10 (ethylene oxide) repeat units.

[0113] residue R 1 Preferred examples for are C3-C18 hydroxy-substituted polyether radicals, especially glycerol-based polyether radicals, and C1-C8 linear alkyl or alkylene groups, where the term polyether specifically includes compounds derived from poly(alkylene oxide)s, in which the alkylene groups of the repeat units are independently selected from C1-C8 alkylene.

[0114] residue R 2 Preferred examples for are straight chain C1-C8 alkylene radicals, more preferably ethylene, propylene, butylene, pentylene, hexylene and heptylene, most preferably propylene and hexylene.

[0115] residue R 3 , R 4 and R 5 Preferred examples for R are straight chain C1-C8 alkyl groups, most preferably R 3 , R 4 and R 5 is a methylene group.

[0116] In a further preferred embodiment of the invention, the organic ammonium group-containing cation of the organic ammonium salt according to the invention is selected from the following group: a. mono- and polyquaternium cations, B. basic amino acid cations; c. Mono- and poly-tertiary amine cations; d. Mono- and poly-secondary amine cations; e. Mono- and poly-primary amine cations.

[0117] According to the present invention, a monoquaternium cation is one having the structure NR 4 + where R is independently selected from alkyl, alkenyl and aryl groups, whereas polyquaternium cations are polycationic cations characterized by the presence of two or more of the above-mentioned quaternary ammonium compounds.

[0118] According to the present invention, basic amino acid cations are cations formed from amino acids having a basic side chain at neutral pH, e.g., lysine, arginine, histidine, by protonation and / or alkylation of the second amino group of zwitterionic amino acids.

[0119] The term also includes cations derived from esters and amides of amino acids by protonation or alkylation of one or more of the amino groups.

[0120] According to the present invention, a mono-tertiary amine cation is a cation having the structure NHR 3 + where R is independently selected from alkyl, alkenyl and aryl groups, whereas polytertiary amine cations are polycationic cations characterized by the presence of two or more of the above-mentioned tertiary ammonium cations.

[0121] According to the present invention, a mono-secondary amine cation is a cation having the structure NH 2 R 2 + where R is independently selected from alkyl, alkenyl and aryl groups, whereas polysecondary amine cations are polycationic cations characterized by the presence of two or more of the aforementioned secondary ammonium cations.

[0122] According to the present invention, a mono-primary amine cation is a cation having the structure NH 3 R + where R is independently selected from alkyl, alkenyl and aryl groups, whereas polyprimary amine cations are polycationic cations characterized by the presence of two or more of the aforementioned primary ammonium cations.

[0123] In another preferred embodiment of the invention, the organoammonium group-containing cation of the organoammonium salt according to the invention has at least 6, preferably at least 10 carbon atoms.

[0124] In yet another preferred embodiment of the present invention, the organoammonium group-containing cation of the organoammonium salt according to the present invention has the formula (I), where x is 2 and R 1 carries a carboxylate anion group and the total charge of the cation is +1.

[0125] R 1 It is preferred that n is the only carboxylate group of the cation and that n is 0 in both of the F groups of the cation.

[0126] Examples of such cations are those derived from arginine, histidine, or lysine by protonation or alkylation and which exhibit two positively charged ammonium moieties and a carboxylate anion moiety.

[0127] In a preferred embodiment of the present invention, the carboxylate anion (COO - ) group-containing anion is selected from the group consisting of the following types of polymeric fatty acid carboxylates: R 7 [(-C(O)-XR 8 ) m+1 -C(O)-XR 9 ] q or R 7 [(XC(O)-R8 ) m+1 -XC(O)-R 9 ] p , In the formula, X, R 7 , R 8 , R 9 , m, p and q are as defined above for formulas (V), (VI), (VII) and (VIII), and in formula R 7 or at least one R 9 , or R 7 and at least one R 9 is one or more carboxylate groups, Preferably X=O, especially The following types of linear polymeric fatty acid carboxylates: - OC(O)-R 7 (-XC(O)-R 8 ) m+1 -XC(O)-R 9 , preferably - OC(O)-R 7 -(OC(O)-R 8 ) m+1 -OC(O)-R 9 and R in the formula 9 is selected from optionally substituted, linear, cyclic, or branched, substituted or unsubstituted monovalent hydrocarbon radicals having up to 36 carbon atoms; For example, the following linear polyfatty acid structure is derived by deprotonation: [ka] [ka] [ka] [ka] [ka] Branched linear polymeric fatty acid carboxylates, i.e., derived from the branched polyfatty acid structure, for example: [ka] Where R = [ka] Where R = [ka] Where R = [ka] or where R = [ka] or where R = [ka] or partial esters of polyfunctional carboxylic acids, in particular branched linear polymeric fatty acid carboxylates derived from partial esters of the dicarboxylic acids succinic acid and maleic acid with castor oil or lesquerella oil, e.g. [ka] where one or two R = [ka] and the remaining two or one R groups = [ka] or [ka] Dendrimer polymeric fatty acid carboxylates, i.e., derived from, for example, the following dendrimer polyfatty acid structure: [ka] Where R = [ka] or where R = [ka] Or the following types: R 7 [(-C(O)-XR 8 ) m+1 -C(O)-XR 9 C(O)O - ] q or ( - O.C. (O) q-1 -R 7 -(C(O)-XR 8 ) m+1 -C(O)-XR 9 C(O)O - and In the formula, X, R 7 , R 8 , R 9 , m, p and q are as defined above for formulae (V), (VI), (VII) and (VIII), e.g. [ka] and These types of carboxylate anions (COO - ) group-containing anions, in particular of the following types: R 7 [(-C(O)-XR 8 ) m+1-C(O)-XR 9 C(O)O - ] q or ( - O.C. (O) q-1 -R 7 -(C(O)-XR 8 ) m+1 -C(O)-XR 9 C(O)O - is preferably a 1-50 valent anion, more preferably 1-10 valent anion, even more preferably 1-5 valent anion, and most preferably a 5-, 4-, 3-, 2- or 1-valent anion.

[0128] In another preferred embodiment of the present invention, the carboxylate anion (COO - The ) group-containing anion comprises at least one moiety of general formula (VIa): (-XC(O)-R 8 ) m -XC(O)-R 9 (VIa) or comprising at least one moiety of general formula (VIIIa) (-C(O)-XR 8 ) m -C(O)-XR 9 (VIIIa) In the formula, X and R 8 and m is as defined above, and R 9 are independently selected from optionally substituted linear, cyclic, or branched, substituted or unsubstituted hydrocarbon radicals having from 1 to 36 carbon atoms, optionally containing one or more groups selected from -O-, -NH-, -C(O)-, -C(S)-, which may be substituted with an OH group, a carboxylate group, or a halide group.

[0129] Radical R 9may be the same or different and represent a hydrocarbyl group selected from optionally substituted linear, cyclic or branched, substituted or unsubstituted hydrocarbon radicals having from 1 to 36 carbon atoms, and preferably linear, branched or cyclic alkyl groups, linear, branched or cyclic alkenyl groups, linear, branched or cyclic alkynyl groups, linear, branched or cyclic alkaryl groups, linear, branched or cyclic aralkyl groups and linear, branched or cyclic aryl groups, such as phenyl, benzyl or tolyl, more preferably having from 6 to 24 carbon atoms, each optionally containing one or more functional groups as defined above.

[0130] In yet another preferred embodiment of the present invention, at least one group R of the organic ammonium salt according to the present invention 9 are straight-chain alkyl and alkenyl groups, in particular straight-chain C6-C24 alkyl groups such as 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, decenyl, Preferably, the alkyl group is selected from straight chain C6-C24 alkenyl groups such as -C(O)-, ...

[0131] Preferably, the carboxylate anion (COO - All terminal groups R of the anion containing the ) group 9 is selected from the linear alkyl or linear alkenyl groups described above, and more preferably all R 9 The groups are selected from C6-C24 alkyl groups, in particular C14-C22 alkyl groups.

[0132] In a further preferred embodiment of the invention, at least one group R of the organic ammonium salt according to the invention 9 is derived from a carboxylic acid or a hydroxycarboxylic acid bearing one or more hydroxyl groups, more preferably from a carboxylic acid or a monohydroxycarboxylic acid, most preferably from a C7-C25 fatty acid bearing no hydroxyl groups as substituents.

[0133] Particularly preferably, at least one group R of the organic ammonium salt according to the invention 9 is derived from a hydroxycarboxylic acid selected from ricinoleic acid, lesquerolic acid, 10-hydroxyoctadecanoic acid, 12-hydroxyoctadecanoic acid, 14-hydroxytetradecanoic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, derived from a dihydroxycarboxylic acid selected from 2,2'-dihydroxymethylpropanoic acid, 9,10-dihydroxystearic acid, derived from gluconic acid, or derived from acetic acid, propionic acid , butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, undecanoic acid, lauric acid, tridecanoic acid, myristic acid, pentadecanoic acid, palmitic acid, margaric acid, stearic acid, oleic acid, linoleic acid, α-linolenic acid, γ-linolenic acid, nonadecylic acid, arachidic acid, mead acid, arachidonic acid, heneicosanoic acid, docosanoic acid, tricosylic acid and lignosenoic acid, and most preferably R 9 is selected from ricinoleic acid, lesquerolic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, palmitic acid, margaric acid, stearic acid, linoleic acid, α-linolenic acid, γ-linolenic acid, oleic acid, nonadecylic acid, and arachidic acid.

[0134] Even more preferably, all groups R 9 are derived from the carboxylic acids and monohydroxy acids mentioned above, most preferably from ricinoleic acid, lesquerolic acid, oleic acid, and stearic acid.

[0135] In an even more preferred embodiment of the present invention, at least one group R of the organic ammonium salt according to the invention 9 represents the alkyl or alkenyl chain of a carboxylic acid or hydroxycarboxylic acid obtained by abstraction of a carboxylate group, where preferably the carboxylic acid is acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic 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, γ-linolenic acid, oleic acid, nonadecylic acid, arachidic acid, mead acid, arachidonic acid, heneicosanoic acid, docosanoic acid, tricosylic acid and lignosenoic acid, hydroxycarboxylic acids such as lesquerolic acid, ricinoleic acid, 10-hydroxyoctadecanoic acid, 12-hydroxyoctadecanoic acid, 14-hydroxytetradecanoic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or dihydroxycarboxylic acids, in particular 2,2'-dihydroxymethylpropanoic acid, 9,10-dihydroxystearic acid, or polyhydroxycarboxylic acids, in particular gluconic acid, more preferably at least one R 9 The radical is derived from palmitic acid, margaric acid, stearic acid, linoleic acid, α-linolenic acid, γ-linolenic acid, oleic acid, nonadecylic acid, arachidic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, ricinoleic acid, lesquerolic acid or 2,2′-dihydroxymethylpropanoic acid, and most preferably at least one R 9 The radicals are derived from oleic acid, stearic acid, lesquerolic acid and ricinoleic acid.

[0136] In a preferred embodiment of the present invention, the carboxylate anion (COO - ) group-containing anions, X=O, R 8is 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, dodecenylene, tridecenylene, tetradecenylene, pentadecenylene, hexadecenylene, heptadecenylene, octadecenylene, nonadecenylene, eicosenylene, henicosenylene, doicosenylene, tricosenylene, and tetraicosenylene, where the groups are most preferably attached by a terminal carbon atom to an adjacent C(O) or O group; R 9 are independently selected from optionally 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, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl, henicosyl, doicosenyl, tricosenyl, and tetraicosenyl, where the groups are most preferably attached by a terminal carbon atom to an adjacent C(O) or O group, and m is 0-10, preferably 1-10, more preferably 1, 2, 3, 4 or 5.

[0137] In another preferred embodiment of the present invention, X=O, The carboxylate anion (COO - At least one group R in the group-containing anion 8is selected from hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, hexadecenylene, heptadecenylene, octadecene, nonadecene, and eicosenylene; At least one R 9 is selected from hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl; and m is 1, 2, 3, 4 or 5; Preferably At least one R 8 are derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid or lesquerolic acid, At least one R 9 is derived from oleic acid, ricinoleic acid or stearic acid, and m is 1, 2, 3, 4 or 5.

[0138] More preferably, X=O, All groups R 8 are derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid or lesquerolic acid, All groups R 9 is derived from oleic acid, ricinoleic acid or stearic acid, and m is 1, 2, 3, 4 or 5.

[0139] In yet another preferred embodiment of the present invention, the organic ammonium salt according to the present invention is represented by the general formula (VI), (VI * ), (VIII) or (VIII *Each of the moieties 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, dodecenylene, tridecenylene, tetradecenylene, pentadecenylene, hexadecenylene, heptadecenylene, octadecenylene, nonadecenylene, eicosenylene, henicosylene, doicosenylene, tricosenylene, and tetraicosenylene. 8 Including, Preferably, the general formula (VI), (VI * ), (VIII) or (VIII * Each of the moieties is optionally hydroxyl-substituted hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, hexadecenylene, heptadecenylene, octadecylene, nonadecylene, eicosylene. 8 Including, and m is 1, 2, 3, 4 or 5; More preferably, the general formula (VI), (VI * ), (VIII) or (VIII * At least one R in each of the portions 8 are derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid or lesquerolic acid, and m is 1, 2, 3, 4 or 5.

[0140] Even more preferably, the compound represented by the general formula (VI), (VI * ), (VIII) or (VIII * ) for all R in each part of 8 are derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid or lesquerolic acid, and m is 1, 2, 3, 4 or 5.

[0141] In a preferred embodiment of the present invention, the carboxylate anion (COO - The anion containing a ) group is a straight-chain carboxylate anion A of the formula - Including, - OC(O)-R 7 -(OC(O)-R 8 ) m+1 -OC(O)-R 9 where m, R 8 and R 9 is as defined above, R 7 are independently selected from optionally substituted, linear, cyclic, or branched, substituted or unsubstituted divalent hydrocarbon radicals having up to 36 carbon atoms; and R 8 +R 9 The total number of carbon atoms in (R per anion 8 and R 9 (Σ carbon atoms) is from 19 to 300, preferably from 25 to 300, more preferably from 35 to 300, even more preferably from 50 to 300, particularly from 35 to 200, more particularly from 35 to 150, even more particularly from 50 to 150; And here R 7 and R 8 is preferably derived from lactic acid, ricinoleic acid, lesquerolic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, and 14-hydroxytetradecanoic acid, most preferably from ricinoleic acid or lesquerolic acid; R 9 is preferably derived from octadecanoic acid, eicosanoic acid, docosanoic acid, 2-ethylhexanoic acid, 2,2-dimethylpropionic acid, neodecanoic acid, oleic acid, and m is preferably 1 to 10, more preferably 1 to 6, even more preferably 1 to 6, in particular 1, 2, 3, 4, 5, 6, 7.

[0142] In a further preferred embodiment of the present invention, the carboxylate anion (COO - The anion containing a ) group is a straight-chain carboxylate anion A of the formula - Including, - OC(O)-R 7 -(OC(O)-R 8 ) m+1 -OC(O)-R 9 m, R in the formula 7 , R 8 and R 9 is as defined above, and in the above formula, R 7 , R 8 and R 9 is selected as follows: [Table 1]

[0143] Preferably, all sequences are selected according to the table above. More preferably, m is 1 to 10, more preferably 1 to 6, in particular 1, 2, 3, 4, 5, 6 or 7.

[0144] In yet another preferred embodiment of the present invention, the carboxylate anion (COO - ) group-containing anion includes a branched linear polymeric fatty acid carboxylate, In particular, glycerin esterified with partial esters of polyfunctional carboxylic acids, in particular branched linear polymeric fatty acid carboxylates derived from partial esters of the dicarboxylic acids succinic and maleic acids with castor oil or lesquerella oil, or with hydroxy fatty acids containing at least one moiety of the formula: Glycerin-OC(O)-R 8 -(OC(O)-R 8 ) m -OC(O)-R 9 During the ceremony R8 is as defined above and is preferably derived from lactic acid, ricinoleic acid, lesquerolic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, 14-hydroxytetradecanoic acid, most preferably derived from ricinoleic acid or lesquerolic acid; R 9 are as defined above and are preferably derived from octadecanoic acid, eicosanoic acid, docosanoic acid, 2-ethylhexanoic acid, 2,2-dimethylpropionic acid, neodecanoic acid, oleic acid, succinic acid and maleic acid, succinic anhydride and maleic anhydride, And in the above formula, m=0 to 20, preferably 1 to 20, more preferably 1 to 10, even more preferably 1 to 6, in particular 0, 1, 2, 3, 4, 5, 6, 7; and R 8 +R 9 The total number of carbon atoms in (R 8 and R 9 (Σ carbon atoms) is from 19 to 300, preferably from 25 to 300, more preferably from 35 to 300, even more preferably from 50 to 300, specifically from 35 to 200, more specifically from 35 to 150, and even more specifically from 50 to 150.

[0145] According to the present invention, the term "branched linear polymeric fatty acid carboxylate" refers to a salt of two or more linear polymeric fatty acid moieties of the following formula, which are branched structures: -OC(O)-R 8 -(OC(O)-R 8 ) m -OC(O)-R 9 and refers to branched compounds containing at least one carboxylate group.

[0146] The term "polyfunctional carboxylic acid" refers to a carboxylic acid compound that further comprises at least one carboxylic acid group.

[0147] The term "esterified glycerin containing at least one moiety of the formula Glycerin-OC(O)-R 8 -(OC(O)-R 8 ) m -OC(O)-R 9 " refers to a glycerol molecule in which at least one of the three hydroxyl groups of glycerol is attached via an ester group to a moiety of the formula: -R 8 -(OC(O)-R 8 ) m -OC(O)-R 9 Here, R 8 , R 9 and m are as defined for the radicals in this embodiment.

[0148] An example of an anion according to this embodiment is an anion obtained by deprotonation of the following structure: [ka] Here, one R = [ka] And the remaining two R groups = [ka] It is.

[0149] In a further preferred embodiment of the present invention, the carboxylate anion (COO - ) group-containing anions include branched linear polymeric fatty acid carboxylates containing at least one moiety of the formula: Glycerin-OC(O)-R 8 -(OC(O)-R 8 ) m -OC(O)-R 9 where there is at least one sequence of the general formula: Glycerin-OC(O)-R 8 -(OC(O)-R8 ) m -OC(O)-R 9 where m, R 8 and R 9 is as defined above and is selected from: [Table 2] Preferably, two sequences are selected according to the table above, while the third hydroxy group of the glycerol group is functionalized to carry a carboxylate group-containing residue.

[0150] Further preferably m is 0 to 10, more preferably 1 to 6, especially 0, 1, 2, 3, 4, 5, 6 or 7.

[0151] In another preferred embodiment of the present invention, the carboxylate anion (COO - ) group-containing anion is a branched or dendrimeric polymeric fatty acid carboxylate anion A of formula (V) - Including, Formula (VI) or (VI * ) R 7 , X, R 8 , R 9 , R 9* and m is as defined above; There, R 7 The radical carries at least one anionic carboxylate group and is preferably derived from a bishydroxymonocarboxylic acid, such as glyceric acid and 2,2-bis-(hydroxymethyl)propionic acid, R 8 is as defined above and is preferably derived from lactic acid, ricinoleic acid, lesquerolic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, 14-hydroxytetradecanoic acid, most preferably from ricinoleic acid or lesquerolic acid; R 9is as defined above, preferably derived from octadecanoic acid, eicosanoic acid, docosanoic acid, 2-ethylhexanoic acid, 2,2-dimethylpropionic acid, neodecanoic acid, and stearic acid, oleic acid, and R 9* in which T is preferably derived from octadecanoic acid, eicosanoic acid, docosanoic acid, 2-ethylhexanoic acid, 2,2-dimethylpropionic acid, neodecanoic acid, stearic acid and oleic acid; m=1 to 20, preferably 1 to 10, more preferably 1 to 6, even more preferably 1 to 6, in particular 1, 2, 3, 4, 5, 6, 7; R 8 +R 9 The total number of carbon atoms in (R 8 and R 9 (Σ carbon atoms) is from 19 to 300, preferably from 25 to 300, more preferably from 35 to 300, even more preferably from 50 to 300, specifically from 35 to 200, more specifically from 35 to 150, and even more specifically from 50 to 150.

[0152] In a further preferred embodiment, the carboxylate anion (COO - ) group-containing anions include branched or dendrimeric polymeric fatty acid structures as described above, Wherein the general formula R 7 (-XC(O)-R 8 ) m -XC(O)-R 9 wherein at least one sequence of X and m as defined above is selected from: [Table 3] Preferably, all such sequence groups are selected according to the table above.

[0153] In a further preferred embodiment of the present invention, the carboxylate anion (COO -) group-containing anions are the following types of carboxylate anions A - Including, R 7 [(-C(O)-XR 8 ) m+1 -C(O)-XR 9 C(O)O - ] q ,or ( - O.C. (O) q-1 -R 7 -(C(O)-XR 8 ) m+1 -C(O)-XR 9 C(O)O - Here, X=O, R 7 , R 8 , R 9 , m and q are as defined above, and Preferably q=2 to 4, in particular 2, 3, 4, R 8 is as defined above and is preferably derived from lactic acid, ricinoleic acid, lesquerolic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, 14-hydroxytetradecanoic acid, most preferably from ricinoleic acid or lesquerolic acid; R 7 is as defined above and is preferably derived from maleic acid, succinic acid, trimellitic acid, pyromellitic acid, and m=0 to 20, preferably 1 to 20, more preferably 1 to 10, even more preferably 1 to 6, even more preferably 1 to 6, in particular 1, 2, 3, 4, 5, 6, 7, and R 8 +R 9 The total number of carbon atoms in (R per anion 8 and R 9 (Σ carbon atoms) is from 19 to 300, preferably from 25 to 300, more preferably from 35 to 300, even more preferably from 50 to 300, specifically from 35 to 200, more specifically from 35 to 150, and even more specifically from 50 to 150.

[0154] In an even more preferred embodiment of the present invention, the carboxylate anion (COO - ) group-containing anions are the following types of carboxylate anions A - Including, R 7 [(-C(O)-XR 8 ) m+1 -C(O)-XR 9 C(O)O - ] q ,or ( - O.C. (O) q-1 -R 7 -(C(O)-XR 8 ) m+1 -C(O)-XR 9 C(O)O - Here, X=O, R 7 , R 8 , R 9 , m and q are as defined above, and General formula R 7 [(-C(O)-XR 8 ) m+1 -C(O)-XR 9 C(O)O - ] q , and ( - O.C. (O) q-1 -R 7 -(C(O)-XR 8 ) m+1 -C(O)-XR 9 C(O)O - wherein the sequence of at least one polyacid ester in [Table 4] Preferably, all such sequences of anions are selected according to the table above.

[0155] Preferably, m is 1 to 10, in particular 1, 2, 3, 4, 5, 6, 7, or 8, and even more preferably in addition q is 1-6, most preferably 2 to 4.

[0156] In another preferred embodiment of the present invention, the organoammonium group-containing cation has the general formula defined above. R 1 (-F) x (I) wherein the cation is selected from the group consisting of x is 1 to 10, preferably 1 to 5, more preferably 1, 2, 3, 4, 5, most preferably 1 and 2; F may be the same or different and is represented by the general formula (II): [ka] R in the formula 1 , R 2 , R 3 , R 4 , R 5 and n is as defined above, and preferably n=0-100, even more preferably 0-50, even more preferably 0-20, and most preferably 0, 1, 2, 3, 4 or 5.

[0157] In yet another preferred embodiment of the present invention, the organoammonium group-containing cation has the general formula defined above. R 1 (-F) x (I) wherein the cation is selected from the group consisting of x=2 and the cation is represented by the general formula (V): [ka] R in the formula 1 , R 2 , R 3 , R 4 , R 5 and n is as defined above, and preferably n=0-1000, preferably 0-100, more preferably 0-50, even more preferably 0-20, and most preferably 0, 1, 2, 3, 4 or 5.

[0158] Examples of cations according to this embodiment are cations derived from the following amino compounds: [ka]

[0159] In a further preferred embodiment of the present invention, the organoammonium group-containing cation has the general formula defined above. R 1 (-F) x (I) wherein the cation is selected from the group consisting of x is 1 to 10, preferably 1 to 5, more preferably 1, 2, 3, 4, or 5, most preferably 1 or 2; R 1 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, particularly 3 to 50 carbon atoms, and more particularly 3 to 20 carbon atoms, and optionally -O-, -NH-, -C(O)-, -C(S)-, [ka] and is selected from optionally substituted monovalent to decavalent hydrocarbon radicals, which may contain one or more groups selected from: Preferably R 1 is a C3-C18 glycerol-based polyether radical or a C1-C8 linear alkylene radical, and F has the general formula (XVII) corresponding to formula (II) with n equal to 0: [ka] And the group F is R 1Attached to the carbon atom of where R 3 , R 4 , R 5 represents hydrogen and 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, particularly 1 to 20 carbon atoms, more particularly 1 to 10 carbon atoms, and optionally -O-, -NH-, -C(O)-, -C(S)-, [ka] and are independently selected from optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals, which may contain one or more groups selected from Preferably R 3 From R 5 is a C1-C8 straight chain alkyl group such as methyl, ethyl, propyl or butyl.

[0160] According to a preferred embodiment of the present invention, the carboxylate anion (COO - The ) group-containing anion is preferably a 1- to 50-valent anion, more preferably a 1- to 10-valent anion, even more preferably a 1- to 5-valent anion, and most preferably a pentavalent, tetravalent, trivalent, divalent or monovalent anion.

[0161] In another preferred embodiment of the present invention, the carboxylate anion (COO - ) group-containing anion comprises at least one moiety of general formula (XI) or (XII): -XC(O)-R x -(XC(O)-R x ) m -XC(O)-R 9 (XI) or -XC(O)-R x -(XC(O)-R x ) m -XC(O)-R 9 (XII) During the ceremony X is O or NR 11 , m=1 to 20, preferably 1 to 10, more preferably 1 to 6, even more preferably 2 to 6, in particular 1, 2, 3, 4, 5, 6; R x +R 9 The total number of carbon atoms (R per anion) x , R 9 Σ carbon atoms) is from 19 to 300, preferably from 25 to 300, more preferably from 35 to 300, even more preferably from 50 to 300, particularly from 35 to 200, more particularly from 35 to 150, even more particularly from 50 to 150, R 11 is as defined above and is preferably hydrogen, n-, iso-, or tert-C 1 -C 22 -alkyl, more preferably hydrogen; R x is optionally OH, -OC(O)-R 9 , -OC(O)-R 8 -(OC(O)-R 8 ) 0-19 -OC(O)-R 9 Replaced by R 8 and R 9 a linear, cyclic or branched, substituted or unsubstituted hydrocarbon radical having from 1 to 36 carbon atoms, preferably from 1 to 24 carbon atoms, more preferably from 1 to 18 carbon atoms, even more preferably from 8 to 18 carbon atoms, excluding the carbon atoms of the radical-containing substituents, preferably derived from a monohydroxycarboxylic acid, in particular glycolic acid, lactic acid, 2-hydroxybutyric acid, 3-hydroxybutyric acid, 4-hydroxybutyric acid, 14-hydroxytetradecanoic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, lesquerolic acid, ricinoleic acid, or a dihydroxycarboxylic acid, in particular 2,2'-dihydroxymethylpropanoic acid, 9,10-dihydroxystearic acid, or a polyhydroxycarboxylic acid, in particular gluconic acid, R 8 is as defined above, R 9is selected from optionally substituted linear, cyclic or branched, substituted or unsubstituted, hydrocarbon radicals having from 1 to 36 carbon atoms, preferably from 1 to 24 carbon atoms, more preferably from 1 to 18 carbon atoms, even more preferably from 8 to 18 carbon atoms, preferably derived from acetic acid, octanoic acid, nonanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, eicosanoic acid, docosanoic acid, 2-ethylhexanoic acid, 2,2-dimethylpropionic acid, 2,2-dimethylheptanoic acid, 2,2-dimethyloctanoic acid, neodecanoic acid, undecyl-10-enoic acid, oleic acid, linoleic acid, linolenic acid, erucic acid, and R 8 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, dodecenylene, tridecenylene, tetradecenylene, pentadecylene, decenylene, hexadecenylene, heptadecenylene, octadecenylene, nonadecenylene, eicosenylene, henicosenylene, doicosenylene, tricosenylene, and tetraicosenylene, more preferably optionally hydroxyl-substituted hexadecylene, heptadecylene, octadecylene, nonadecenylene, eicosylene, hexadecenylene, heptadecenylene, octadecenylene, nonadecenylene, eicosenylene, and most preferably each R 8 are preferably independently selected from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid or lesquerolic acid.

[0162] In a preferred embodiment according to the present invention, the organoammonium group-containing cation has the general formula defined above: R 1 (-F) x (I) wherein R is selected from the group consisting of cations according to the formula 1 is selected from the group consisting of monovalent to 18valent, preferably divalent to 18valent, more preferably divalent to 6valent, even more preferably divalent, trivalent and tetravalent, optionally -O-, -C(O)-, OH or amido substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbyl radicals: which are derived from primary, secondary and tertiary amines and quaternary ammonium compounds having at least one, preferably more than one, more preferably three and even more preferably more than three carbon atoms, In particular, it is derived from - primary amines such as C1 to C24 primary amines, i.e. methylamine, ethylamine, propylamine, isopropylamine, butylamine, hexylamine, cyclohexylamine, octylamine, 2-ethylhexylamine, decylamine, undecenylamine, dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, oleylamine, OH-functionalized primary amines, i.e. ethanolamine, glucamine, aminoglycerin, Jeffamine, a polyether-based primary amine, i.e., mono-, di-, and trifunctional primary amine based on polyethylene oxide and polypropylene oxide 登録商標 Series, e.g. Jeffamine 登録商標 M600, 1000, 2005, 2070, Jeffamine 登録商標 XTJ-435, 436, Jeffamine 登録商標 D230, 400, 2000, 4000, Jeffamine 登録商標 ED HK-511, 600, 900, 2003, Jeffamine 登録商標 EDR148, 176, Jeffamine 登録商標 T403, 3000, 5000, It is derived from derived from the condensation products of epoxy compounds, in particular glycidyl ethers and alcohols, in particular methanol, ethanol, 2-propanol, 1-butanol, tert-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, glycerin, diglycerin, triglycerin and higher linear or branched oligoglycerins, trimethylolpropane, castor oil (ricinoleic acid triglyceride), pentaerythritol, sorbitol, polyethylene glycols, such as diethylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, etc., or dipropylene glycol (for example poly(alkylene oxides) such as (ethylene oxide)-, (propylene oxide)- and / or (butylene oxide)-based polyethers derived from 2,2'-oxydi-1-propanol, 1,1'-oxydi-2-propanol, and 2-(2-hydroxypropoxy)-1-propanol), polypropylene glycols such as tripropylene glycol, tetrapropylene glycol, pentapropylene glycol, derived from mixed (ethylene oxide) and (butylene oxide)-based copolyethers, derived from mixed (propylene oxide)- and (butylene oxide)-based copolyethers, and derived from mixed (ethylene oxide)- and (propylene oxide)- and (butylene oxide)-based copolyethers, or preferably glycidyl esters and acids, in particular neodecanoic acid, and ammonia. - derived from basic amino acids such as lysine, arginine, histidine or their ester or amide derivatives - secondary amines derived from secondary amines, in particular C1 to C24 secondary amines such as N-methylamines, such as dimethylamine, N-methyloctylamine, N-methyldodecylamine, N-methyloctadecylamine, N-ethylamines, such as diethylamine, N-butylamines, such as dibutylamine, piperazine, morpholine, OH-functionalized secondary amines such as diethanolamine, N-methylglucamine, N-methylaminoglycerin, Jeffamine, a difunctional secondary amine based on polyethylene oxide and polypropylene oxide. 登録商標 Polyether-based secondary amines such as those in the Jeffamine series, in particular 登録商標 SD231, 401, 404, 2001 (Huntsman), or polyethyleneimine, i.e., Lupasol 登録商標 Series (BASF) - derived from condensation products of epoxy compounds, in particular glycidyl ethers and alcohols, in particular methanol, ethanol, 2-propanol, 1-butanol, tert-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, glycerin, diglycerin, triglycerin and higher linear or branched oligoglycerins, trimethylolpropane glycerol, castor oil (ricinoleic acid triglyceride), pentaerythritol, sorbitol, polyethylene glycols such as diethylene glycol, triethylene glycol, tetraethylene glycol, and pentaethylene glycol, and the like, or 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, poly(alkylene oxides) such as (ethylene oxide)-, (propylene oxide)- and / or (butylene oxide)-based polyethers derived from polypropylene glycols such as ethylene glycols, derived from mixed (ethylene oxide)- and (butylene oxide)-based copolyethers, derived from mixed (propylene oxide)- and (butylene oxide)-based copolyethers, and derived from mixed (ethylene oxide)- and (propylene oxide)- and (butylene oxide)-based copolyethers; or preferably Preferably, glycidyl esters and acids, in particular neodecanoic acid, and primary amines, i.e. methylamine, ethylamine, butylamine, cyclohexylamine, octylamine, 2-ethylhexylamine, undecenylamine, dodecylamine, hexadecylamine, stearylamine, oleylamine, ethylenediamine, 1,2-propylenediamine, 1,3-propylenediamine, 1,4-butanediamine, 1,6-hexanediamine, 1,10-decanediamine, 1,12-dodecanediamine, basic amino acids, e.g. N-methyllysine, - derived from tertiary amines, in particular trimethylamine, triethylamine, tributylamine, N,N-dimethylethanolamine, N,N-dimethylpropanolamine, N-methylimidazole, N,N,N',N'-tetramethyl-1,2-diaminoethane, N,N,N',N'-tetramethyl-1,4-diaminobutane, N,N,N',N'-tetramethyl-1,6-diaminohexane, N,N,N',N'',N''-pentamethyl-diethylenetriamine, N,N,N',N'',N''-pentamethyl-dipropylenetriamine amine, bis-(2-dimethylaminoethyl)ether, bis-(2-dimethylaminopropyl)ether, 2,2'-dimorpholinodiethylether, N,N-bis-(3-dimethylaminopropyl)-N-isopropanolamine, N,N,N'-trimethylaminoethyl-ethanolamine, 1,3,5-tris(3-(dimethylamino)propyl)-hexahydro-s-triazine, N-methylmorpholine, N-ethylmorpholine, N,N'-dimethylpiperazine, N,N-dimethylbenzylamine, N,N-dimethylcyclohexylamine derived from condensation products of epoxy compounds, in particular glycidyl ethers and alcohols, in particular methanol, ethanol, 2-propanol, 1-butanol, tert-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, glycerin, diglycerin, triglycerin and higher linear or branched oligoglycerins, trimethylolpropane, Castor oil (ricinoleic acid triglyceride), pentaerythritol, sorbitol, polyethylene glycols such as diethylene glycol, triethylene glycol, tetraethylene glycol, and pentaethylene glycol, and the like, or 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, poly(alkylene oxides) such as (ethylene oxide)-, (propylene oxide)- and / or (butylene oxide)-based polyethers derived from polypropylene glycols such as propylene glycols, derived from mixed (ethylene oxide)- and (butylene oxide)-based copolyethers, derived from mixed (propylene oxide)- and (butylene oxide)-based copolyethers, and derived from mixed (ethylene oxide)- and (propylene oxide)- and (butylene oxide)-based copolyethers, or preferably glycols. sidyl esters and acids, in particular neodecanoic acid, and primary or secondary amino-functional amines, in particular methylamine, ethylamine, butylamine, cyclohexylamine, octylamine, 2-ethylhexylamine, undecenylamine, dodecylamine, hexadecylamine, stearylamine, oleylamine, ethylenediamine, 1,2-propylenediamine, 1,3-propylenediamine, 1,4-butanediamine, 1,6-hexanediamine, 1,10-decanediamine, 1,12-dodecanediamine, N,N-dimethylethylenediamine, N,N-Dimethylpropylenediamine, N,N,N',N'-Tetramethyl-diethylenetriamine, N,N,N',N'-Tetramethyl-dipropylenetriamine, N-Methylpiperazine, -carboxylic acids, in particular C6-C24 fatty acids, i.e. hexanoic acid, 2-ethylhexanoic acid, octanoic acid, decanoic acid, undecenoic acid, dodecanoic acid, tetradecanoic acid, hexadecenoic acid, octadecanoic acid, oleic acid, ricinoleic acid, lesquerolic acid, 12-hydroxystearic acid, di- and higher carboxylic acids, i.e. succinic acid, sebacic acid, trimellitic acid, and primary-tertiary amines, i.e. N,N-dimethylpropylenediamine, N,N-dimethylethylenediamine, N-dodecyl-N-bis-(propylamine), and also secondary-tertiary amines, i.e. N,N,N',N'-tetramethyl-diethylenetriamine, N,N,N',N'-tetramethyl-dipropylenetriamine, N-methylpiperazine, N-ethylpiperazine. - Derived from monoquaternary ammonium compounds, e.g. C1-C30 tetraalkyl-substituted ammonium compounds, preferably Cl - , Br - , C.H. 3 -O-SO 3 - or OH - Compounds with counterions, i.e., compounds with identical alkyl substituents, i.e., (C 2 H 5 ) 4 N + Cl - , (C 2 H 5 ) 4 N + OH - , (C 4 H 9 ) 4 N + Br - , (C 4 H 9 ) 4 N + OH -, preferably mono-long alkyl tri-short alkyl quaternary ammonium salts or di-long alkyl di-short alkyl quaternary ammonium salts, compounds with different alkyl substituents, where one or two of the alkyl substituents are selected from aliphatic or aromatic groups of about 8 to about 30 carbon atoms, alkoxy groups having up to about 30 carbon atoms, polyoxyalkylene groups, alkylamide groups, hydroxyalkyl groups, aryl groups or alkylaryl groups, the other alkyl groups being independently selected from aliphatic or aromatic groups of about 1 to about 8 carbon atoms, alkoxy groups having up to about 8 carbon atoms, polyoxyalkylene groups, alkylamide groups, hydroxyalkyl groups, aryl groups or arylalkyl groups, the aliphatic groups may contain, in addition to carbon and hydrogen atoms, ether linking groups and other groups such as amino groups, the longer chain aliphatic groups, e.g., aliphatic groups of about 8 or more carbon atoms, may be saturated or unsaturated, preferably one alkyl group is selected from alkyl groups of about 8 to about 30 carbon atoms, more preferably from about 14 to about 26 carbon atoms, even more preferably from about 14 to 22 carbon atoms, the other alkyl groups being independently selected from CH 3 , C 2 H 5 , C 2 H 4 OH, CH 2 C 6 H 5 and mixtures thereof, and the counter ion is Cl. - , Br - , C.H. 3 OSO 3 - and mixtures thereof. The C1-C30 tetraalkyl substituted ammonium compound contains an ester moiety and is preferably Cl - , Br - , C.H. 3 -O-SO 3 - and preferably cationic mono- and diester quats based on saturated or unsaturated fatty acids, with 10 to 22, preferably 10 to 18 carbon atoms in the alkyl chain derived from the fatty acid. Ethoxylated C10-C18 saturated and unsaturated monoester quats, such as cocoyl pentaethoxymethylammonium methosulfate C10-C18, preferably C16-C18, saturated and unsaturated diester quats derived from triethanolamine, e.g. [ka] wherein R is independently selected from a C9-C17 alkyl or alkenyl group, preferably R is independently selected from a C15-C17 alkyl or alkenyl group. Saturated and unsaturated triester quats of C10-C18, preferably C16-C18, derived from triethanolamine, such as [ka] wherein R is independently selected from a C9-C17 alkyl or alkenyl group, preferably R is independently selected from a C15-C17 alkyl or alkenyl group. Saturated and unsaturated ester quats of C10-C18, preferably C16-C18, derived from N-methyl-diethanolamine, e.g. [ka] wherein R is independently selected from a C9-C17 alkyl or alkenyl group, preferably R is independently selected from a C15-C17 alkyl or alkenyl group. C10-C18, preferably C16-C18 saturated and unsaturated ester quats derived from N,N-dimethyl-3-aminopropane-1,2-diol, e.g. [ka] wherein R is independently selected from a C9-C17 alkyl or alkenyl group, preferably R is independently selected from a C15-C17 alkyl or alkenyl group. C16-C18 saturated and unsaturated ester quats derived from N-dimethyl-diisopropanolamine having the formula [ka] Where R = C15-C17 alkyl or alkenyl group, and A - = monovalent cation, In particular dioleoylisopropyldimethylammonium methosulfate, dioleoylisopropyldimethylammonium chloride, dipalmitoylisopropyldimethylammonium methosulfate, dipalmitoylisopropyldimethylammonium chloride, bis-(isostearoyl / oleoylisopropyl)dimethylammonium methosulfate, bis-(isostearoyl / oleoylisopropyl)dimethylammonium chloride, - derived from symmetric or asymmetric head- or tail-bridged diquaternary ammonium compounds, i.e. gemini quats, in particular diquaternary compounds comprising at least one, preferably at least two C10-C30, more preferably C10-C22, even more preferably C10-C18 alkyl groups, in particular head-bridged diquaternary compounds, For example, alkyl bridge-containing, preferably C2-C30 alkyl bridge-containing diquaternary compounds, such as those of the formula: [ka] For example, ether and ester bridged, preferably C4-C30 ether and ester bridged diquaternary compounds, such as [ka] [ka] [ka] where n is independently selected from 0 to 24 [ka] For example, diquaternary ammonium compounds that are hydroxyalkyl bridged, preferably glycerol, more preferably containing a C3-C30 glycerol bridge, such as the following formula: [ka] or [ka] where R is independently selected from a C1-C25 alkyl group or a C2-C25 alkenyl group. For example, diquaternary ammonium compounds comprising a fatty acid or fatty alcohol ester moiety, preferably a C6-C30, preferably a C10-C30, more preferably a C10-C22, even more preferably a C16-C18 fatty acid or fatty alcohol ester moiety, such as diquaternary ammonium compounds of the formula [ka] [ka] wherein n is independently selected from 2 to 22, and m is independently selected from 2 to 6. [ka] [ka] [ka] -Especially derived from triquaternary ammonium compounds Preferably, triquaternary compounds containing at least one, preferably at least two, C10-C30, more preferably three C10-C22, even more preferably C10-C18 alkyl groups, such as triquaternary compounds of the formula [ka] In particular, polyquaternary compounds, preferably polyquaternium compounds registered in the INCI, namely Polyquaternium 1 to Polyquaternium 113, are derived from the polyquaternium compounds listed in the table below. [Table 5] derived in particular from polyquaternary compounds based on polysaccharides, preferably cellulose, guar gum, chitin and chitosan, more preferably quaternized cellulose and crosslinked quaternized cellulose (hydrogels), for example quaternized cellulose according to the structure [ka] Quaternary cellulose (QC), the structure in the formula indicates the repeating unit of the corresponding polymer Quaternary cellulose with the following structure: [ka] Quaternary cellulose, n>1 A hydrogel having the following structure: [ka] n>1 in the hydrogel, or [ka] which shows the structure of the repeating unit of the corresponding polymer. That is, quaternized hydroxyethyl cellulose and ethoxylated cellulose, e.g. [ka] where n>1, x>1, y>1 [ka] where n>1 [ka] where n>2, or [ka] Quaternized guar gum, for example of the formula [ka] or obtained from the following reaction mechanism: [ka] and in particular commercially available guar gum based products, such as guar hydroxypropyltrimonium chloride. Quaternized chitin, for example, products (1) and (2) obtained in the reaction scheme shown below: [ka] and quaternized chitosan, in particular N-quaternized chitosan, O-quaternized chitosan, N,O-quaternized chitosan, such as (N-(2-hydroxypropyl)-3-trimethylammonium chitosan chloride (HTCC), Q-chitosan or TMCTPCHT, obtained in the reaction scheme shown below. [ka] [ka] [ka] or the structure obtained in the reaction shown below [ka] [ka]

[0163] According to a preferred embodiment of the present invention, the organic ammonium group-containing cation of the organic ammonium salt cation has the general formula defined above. R 1 (-F) x (I) wherein R is selected from the group consisting of cations according to the formula 1 teeth - selected from monovalent to 18valent, preferably divalent to 18valent, more preferably divalent to hexavalent, even more preferably divalent, trivalent and tetravalent, optionally OH, amino or amido substituted, linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals, which are derived from alkyl halides having more than one, preferably more than two carbon atoms, for example alkyl chlorides, bromides, iodides, such as 1,3-dichloropropane, 1,3-dichlorobutane, 1,4-dichlorobutane, dichloro-monohydroxypropane isomers, 1,2,3-trichloropropane, 1,2-dichlorohexanediol, 1,2-dichlorohexane, or the respective bromides and iodides. - selected from monovalent to 18-valent, preferably divalent to 18-valent, more preferably divalent to 6-valent, even more preferably divalent, trivalent and tetravalent, optionally OH, amino or amido substituted, linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals, which They are derived from esters of halogenated carboxylic acids, preferably chlorocarboxylic acids, having in total (esters) more than two, preferably more than three, carbon atoms, such as chloroacetic acid, 3-chloropropionic acid, 4-chlorobutyric acid or the respective bromocarboxylic acids and alcohols, in particular 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, glycerin, diglycerin, triglycerin and higher linear or branched oligoglycerins, trimethylolpropane, castor oil (ricinoleic acid triglyceride), pentaerythritol, sorbitol, such as diethylene glycol, triethylene glycol, tetraethylene glycol, and and pentaethylene glycol and the like, or 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, pentapropylene glycol; from mixed (ethylene oxide) and (butylene oxide)-based copolyethers; from mixed (propylene oxide)- and (butylene oxide)-based copolyethers; and from mixed (ethylene oxide)- and (propylene oxide)- and (butylene oxide)-based copolyethers; - selected from 1 to 18 valent, preferably 2 to 18 valent, more preferably 2 to 6 valent, even more preferably 2, 3 and 4 valent, optionally OH-substituted, linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbyl radicals, which The epoxy compounds may be derived from ethers or esters of epoxy compounds having a total of more than three, preferably more than four, carbon atoms, preferably glycidyl ethers, by ring-opening with alcohols, in particular 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, glycerin, diglycerin, triglycerin and higher linear or branched oligoglycerins, trimethylolpropane, castor oil (ricinoleic acid triglyceride), pentaerythritol, sorbitol, polyols such as diethylene glycol, triethylene glycol, tetraethylene glycol, and pentaethylene glycol, among others. poly(alkylene oxides) such as (ethylene oxide)-, (propylene oxide)- and / or (butylene oxide)-based polyethers derived from ethylene glycol or derived from dipropylene glycol (e.g. derived from 2,2'-oxydi-1-propanol, 1,1'-oxydi-2-propanol, and 2-(2-hydroxypropoxy)-1-propanol), polypropylene glycols such as tripropylene glycol, tetrapropylene glycol, pentapropylene glycol, derived from mixed (ethylene oxide) and (butylene oxide)-based copolyethers, derived from mixed (propylene oxide)- and (butylene oxide)-based copolyethers, and derived from mixed (ethylene oxide)- and (propylene oxide)- and (butylene oxide)-based copolyethers, or preferably glycidyl esters and acids, in particular neodecanoic acid, - selected from monovalent to 18-valent, preferably divalent to 18-valent, more preferably divalent to 6-valent, even more preferably divalent, trivalent and tetravalent, optionally OH-substituted, linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals, which are Ethers of epoxy compounds having a total of more than 7, preferably more than 8, carbon atoms, preferably glycidyl ethers, with di- to hexavalent carboxylic acids, in particular maleic acid, succinic acid, adipic acid, sebacic acid, itaconic acid, tartaric acid, trimellitic acid, dimer fatty acids, Particularly preferred are carboxyl (-C(O)OH)-functionalized polyesters formed by condensation of di- to hexavalent carboxylic acids, such as maleic acid, succinic acid, adipic acid, sebacic acid, itaconic acid, tartaric acid, trimellitic acid, dimer fatty acids, with di- to hexavalent alcohols as mentioned above or with alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide, with compounds containing at least one glycidoxy group, such as ethers of glycidol, diglycidyl ether, glycerol diglycidyl ether, glycerol triglycidyl ether and oligomeric glycerol glycidyl ether, butanediol diglycidyl ether, in particular succinic acid, maleic acid and tartaric acid, dimer fatty acids with glycerol diglycidyl ether, condensation products of polyesters, particularly preferred are oligomeric hydroxycarboxylic acids, in particular oligomeric lactic acid, 12-hydroxystearic acid, lesquerolic acid, ricinoleic acid. - selected from monovalent to 18-valent, preferably divalent to 18-valent, more preferably divalent to 6-valent, even more preferably divalent, trivalent and tetravalent, optionally OH-substituted, linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals, which are They are derived from esters of halogenated carboxylic acids, preferably chlorocarboxylic acids, having a total of more than 5, preferably more than 6, carbon atoms, such as chloroacetic acid, 3-chloropropionic acid, 4-chlorobutyric acid or the respective bromocarboxylic acids, with OH-functionalized polyesters, particularly preferably formed by condensation of di- to hexavalent carboxylic acids, such as maleic acid, succinic acid, adipic acid, sebacic acid, itaconic acid, tartaric acid, trimellitic acid, dimer fatty acids, with di- to hexavalent alcohols as mentioned above or with alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide, with compounds containing at least one glycidoxy group, such as glycidol, diglycidyl ether, glycerol diglycidyl ether, glycerol triglycidyl ether and oligomeric glycerol glycidyl ether, butanediol diglycidyl ether, in particular the condensation products of succinic acid, maleic acid and tartaric acid or dimer fatty acids with glycerol diglycidyl ether.

[0164] In a further preferred embodiment of the present invention, the organoammonium group-containing cation has the general formula defined above. R 1 (-F) x (I) wherein R is selected from the group consisting of cations according to the formula 1 is selected from poly(alkylene oxide) groups, preferably from poly(alkylene oxide) groups of general formula (XIII): -[CH 2 CH 2 O] q1 -[CH 2 CH(CH 3 )O] r1 -[CH 2 CH(C 2 H 5 )O] s1 -{[CH 2 CH 2 ] q2 -[CH 2 CH(CH 3 )] r2 -[CH 2 CH(C 2 H5 )] s2}-(XIII) where q1=0 to 49, preferably 0 to 10, more preferably 1 to 10, even more preferably 1 to 5; r1=0 to 32, preferably 0 to 10, more preferably 1 to 10, even more preferably 1 to 5; s1=0 to 24, preferably 0 to 10, more preferably 1 to 10, even more preferably 1 to 5; q2=0 or 1, r2=0 or 1, s2=0 or 1, and Σ(q2+r2+s2)=1, provided that the total number of carbon atoms in the poly(alkylene oxide) group is from 2 to 100, preferably from 2 to 50, more preferably from 2 to 30, even more preferably from 2 to 20, especially from 2 to 15, or R 1 is selected from divalent hydrocarbon radicals derived from oligoglycerols of general formula (XIV): -[CH 2 CH(R 12 )CH 2 O] t1 -[CH 2 CH(R 12 )CH 2 )] t2 - (XIV) where t1=0 to 32, preferably 0 to 10, more preferably 1 to 10, even more preferably 1 to 5, in particular 1 and 2; t2=1, R 12 =OH or -OC(O)-R 6 -N + (R 3 , R 4 , R 5 ), Here, R 3 , R 4 , R 5 and R 6 is as defined above, provided that the total number of carbon atoms is from 2 to 100, preferably from 2 to 50, more preferably from 2 to 30, even more preferably from 2 to 20, in particular from 2 to 15, or R 1 teeth Divalent hydrocarbon radicals of general formula (XV) containing at least one ester group: -[CH 2 CH 2 O] q1 -R 13 -[CH 2 CH 2 O] q1 -[CH 2 CH 2 ] q2 - (XV) where q1 is the same or different and is as defined above, and q2=1; and a divalent hydrocarbon radical of general formula (XVI) containing at least one ester group: -[CH 2 CH(R 12 )CH 2 O] t1 -R 13 -[CH 2 CH(R 12 )CH 2 O] t1 -[CH 2 CH(R 12 )CH 2 )] t2 - (XVI) where t1, t2 and R 12 is as defined above, and R 13 is -C(O)C(O)O-, -C(O)(CH 2 ) 1-8 is selected from succinic acid, adipic acid, sebacic acid, or -C(O)(C 6 H 4 )C(O)O-, i.e. phthalic acid and terephthalic acid, -C(O)CH=CHC(O)O-, -C(O)C(=CH 2 )-CH 2 Derived from -C(O)O-, -C(O)CH(OH)CH(OH)C(O)O-, However, R13 is from 2 to 100, preferably from 2 to 50, more preferably from 2 to 30, even more preferably from 2 to 20, especially from 2 to 15, Preferably, q2=0, and one or two of q1, r1 and s1 are 0, and more preferably q2=0, r1 and s1 are 0, or q2=0, q1 and s1 are 0, or R 1 is a group containing one or more, for example from one to five, groups -O-, which are preferably ether groups but which can form ester groups together with the carbonyl group and are preferably groups R 1 is substituted with one or more hydroxyl groups.

[0165] In a preferred embodiment of the present invention, the carboxylate anion (COO - ) group-containing anions of formula (VI), (VI * ) or (VIII), (VIII * ) in at least one of the portions, two or more different R 8 The base exists.

[0166] Formula (VI), (VI * ) or (VIII), (VIII * ) at least two different groups R 8 The presence of the different groups R results when at least two different types of hydroxy- or amino-substituted carboxylic acid derivatives are used in the preparation of such chain structures. 8 may differ from each other in the number of carbon atoms, may differ with respect to the number and position of double bonds, if present, and / or may differ with respect to the position of the substituents and the position of the attachment to adjacent groups. They may differ with respect to whether they are straight-chained or branched.

[0167] In at least one group G or Y, R 8 Preferably, independently represent hydrocarbyl groups derived from ricinoleic acid and 12-hydroxystearic acid.

[0168] In a further preferred embodiment of the present invention, the carboxylate anion (COO - ) group-containing anions of formula (VI), (VI * ) or (VIII), (VIII * In at least one of the moieties, a group R 8 and R 9 or R 8 and R 9* are not based on the same carboxylic acid structure.

[0169] Preferably, the anion of the organic ammonium salt is represented by the formula (VI), (VI * ), (VIII) or (VIII * ) constitutes an internal member of the estolide chain structure. 8 R is a group different from 9 or R 9* It is terminated by.

[0170] More preferably, R 8 and R 9 or R 8 and R 9* differ from each other with respect to the number of carbon atoms, the number or position of double bonds, if present, or the carbon chain of the group, or with respect to the positions of the oxygen and nitrogen atoms attached to the carbon chain of the group. The carboxylic acid structures from which the groups are derived may also differ by two or more of these features.

[0171] In another preferred embodiment of the present invention, the carboxylate anion (COO - In the anions containing the aryl group, p is 2-6; R 7is selected from di- to hexa-valent linear, branched or cyclic alkylene groups, linear, branched or cyclic alkenylene groups, linear, branched or cyclic alkynylene groups, linear, branched or cyclic alkarylene groups, linear, branched or cyclic aralkylene groups, and linear, branched or cyclic arylene groups, such as phenylene, benzylene or tolylene groups, in particular those groups having from 1 to 1000 carbon atoms, more in particular from 1 to 150 carbon atoms; and at least one group G is represented by the general formula (VI * ), -R 8 (-XC(O)-R 8 ) m -XC(O)-R 9* (VI * ) R in the formula 8 , R 9* and m is as defined above, or The carboxylate anion (COO - In the anions containing the aryl group, q is 2-6; R 7 is selected from di- to hexa-valent linear, branched or cyclic alkylene groups, linear, branched or cyclic alkenylene groups, linear, branched or cyclic alkynylene groups, linear, branched or cyclic alkarylene groups, linear, branched or cyclic aralkylene groups, and linear, branched or cyclic arylene groups, such as phenylene, benzylene or tolylene groups, in particular those groups having from 1 to 1000 carbon atoms, more in particular from 1 to 150 carbon atoms; and at least one group Y is represented by the general formula (VIII * ), -R 8 (-C(O)-XR 8 ) m -C(O)-XR 9* (VIII * ) R in the formula 8 , R 9* and m is as defined above.

[0172] According to this embodiment, it is preferred that in formula (V) p is 2, 3 or 4, most preferably p is 2, or in formula (VII) q=2, 3 or 4, most preferably q is 2. It is also preferred that in the compounds of general formula (V) R 7 is preferably selected from linear, branched or cyclic alkylene groups having 1 to 150 carbon atoms, more preferably selected from linear alkylene groups having 1 to 12 carbon atoms, or in formula (VII), R 7 is preferably selected from linear, branched or cyclic alkylene groups having 1 to 150 carbon atoms, more preferably from linear alkylene groups having 1 to 12 carbon atoms.

[0173] In a further preferred embodiment of the present invention, the carboxylate anion (COO - ) group-containing anion, where X=O; p is 2, R 7 is selected from divalent linear, branched and cyclic alkylene radicals, in particular linear C1-C22 alkyl radicals, such as methylene, ethylene, n-propylene, n-butylene, n-pentylene, n-hexylene, n-heptylene or n-octylene radicals, and also from branched C1-C22 alkylene radicals, such as isopropylene, isobutylene, tert-butylene, isobutylene, tert-pentylene, neopentylene and 2-ethylhexylene radicals, preferably ethylene, n-propylene, n-butylene, n-pentylene and n-hexylene, and at least one group G is represented by one or more general formulas (VI * ) part, -R 8 (-XC(O)-R 8 ) m -XC(O)-R 9* (VI * ) R in the formula 8 , R 9* and m is as defined above; or The carboxylate anion (COO - ) group-containing anion, where X=O; q is 2, R 7 is selected from divalent linear, branched and cyclic alkylene radicals, in particular linear C1-C22 alkyl radicals, such as methylene, ethylene, n-propylene, n-butylene, n-pentylene, n-hexylene, n-heptylene or n-octylene radicals, and also from branched C1-C22 alkylene radicals, such as isopropylene, isobutylene, tert-butylene, isobutylene, tert-pentylene, neopentylene and 2-ethylhexylene radicals, preferably ethylene, n-propylene, n-butylene, n-pentylene and n-hexylene, and at least one group Y is selected from the group represented by one or more general formulae (VIII * ) part, -R 8 (-C(O)-XR 8 ) m -C(O)-XR 9* (VIII * ) R in the formula 8 , R 9* and m is as defined above.

[0174] Preferably, R 8 is derived from lactic acid, ricinoleic acid, lesquerolic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, 14-hydroxytetradecanoic acid, most preferably from ricinoleic acid or lesquerolic acid.

[0175] In a particularly preferred embodiment according to the invention, one or more compounds of the general formula (VI * ) moiety of the formula (V) - ) group-containing anions -R 8 (-XC(O)-R 8 ) m -XC(O)-R 9* (VI* ) R in the formula 8 , R 9* and m is as defined above; or one or more of the general formula (VIII * ) moiety of the formula (VII) - ) group-containing anions -R 8 (-C(O)-XR 8 ) m -C(O)-XR 9* (VIII * ) R in the formula 8 , R 9* and m is as defined above; One or more groups R 9* are each terminated with three or more groups -OC(O)-T, preferably each terminated with four or more groups -OC(O)-T, and most preferably each terminated with from four to twelve groups -OC(O)-T, where T is as defined above.

[0176] wherein R preferably includes a branched structure. 9* are terminated with 3 to 10 groups -OC(O)-T, whereas dendrimer structures containing at least two branched structures are preferably terminated with 4 to 20 groups -OC(O)-T.

[0177] According to another preferred embodiment of the present invention, one or more compounds of the general formula (VI * ) portion of the formula (V) - ) group-containing anions, -R 8 (-XC(O)-R 8 ) m -XC(O)-R 9* (VI * ) R in the formula 8 , R 9* and m is as defined above, or one or more of the general formulae (VIII) containing (VII) *) part -R 8 (-C(O)-XR 8 ) m -C(O)-XR 9* (VIII * ) R in the formula 8 , R 9* and m is as defined above; One or more groups R 9* each of which contains at least two branched structures of the general formula: -C(O)-B(-O-) b where B is a straight or branched chain hydrocarbon group having 2-20 carbon atoms, b is 2 or greater, and the b group (-O-) attached to the B group on one side is attached to a carbon atom which is in turn attached to a CH 2 It may be a carbon atom of a group or a carbon atom of a carbonyl group.

[0178] Branched chain structures of the general formula defined above -B(-O-) b The presence of the group R allows for branched structures which may be terminated by two or more groups -OC(O)-T. 9* and having the general formula defined above -C(O)-B(-O-) b The presence of two or more further branched structures of R 9* from the bond linkage to the rest of the molecule and further to the group R 9* This leads to the formation of structures with several branching points that may be arranged in series or in parallel up to the end of R. However, apart from the IUPAC definition for a dendrimer molecule [see A. Fradet et al., Pure and Applied Chemistry, 91(3), 523-561: Nomenclature and Terminology of Dendrimers and Hyperbranched Polymers with Regular Dendrons (IUPAC Recommendations 2017)], a dendron does not have to contain only repeating units of the dendritic structure and terminal structures, and R 9* The free valence of R 9*It is not necessary that each of the paths from the valence atom attaching the to the remainder of the molecule to any of the terminal groups contain the same number of constitutional repeat units.

[0179] More preferably, the branched structure has the general formula defined above. -B(-O-) b All groups (-O-) are branched structures of the general formula defined above. -C(O)-B(-O-) b has been replaced by

[0180] Also preferably, one or more groups R 9* has three or more branched structures -C(O)-B(-O-) b , more preferably containing 3-5 such branched structures.

[0181] In this embodiment, it is preferred that b is independently selected from the range of 2-6, more preferably from the range of 2-4, for both branch structures.

[0182] In a further preferred embodiment according to the present invention, the carboxylate anion (COO - ) group-containing anions, one or more groups R 9* The general formula -B(-O-) b or -C(O)-B(-O-) b One or more of the branched structures are independently derived from glyceric acid, 2,2-dihydroxymethylpropionic acid, gluconic acid, maltobionic acid, and lactobionic acid.

[0183] Preferably, the group R 9* are independently selected from 2,2-dihydroxymethylpropionic acid, more preferably from at least one group R 9* All branched structures in are derived from 2,2-dihydroxymethylpropionic acid.

[0184] Even more preferably, all groups R 9* All of the branched structures present in the compounds of formula (V) or (VII) are derived from the same polyhydroxycarboxylic acid.

[0185] According to another preferred embodiment of the present invention, a compound represented by the following general formula (VI * ) of formula (V) containing one or more moieties of - ) group-containing anions, -R 8 (-XC(O)-R 8 ) m -XC(O)-R 9* (VI * ) R in the formula 8 , R 9* and m is as defined above; or the following general formula (VIII * ) containing one or more moieties of the formula (VII) - ) group-containing anions, -R 8 (-C(O)-XR 8 ) m -C(O)-XR 9* (VIII * ) R in the formula 8 , R 9* and m is as defined above; One or more groups R 9* are each terminated by two or more groups of the structure -R 8 (-XC(O)-R 8 ) t -XC(O)-T, R in the formula 8 and T is as defined above, and X=O, t is independently 0-12, preferably t is independently 0-6, and most preferably t is independently 0, 1, 2 or 3.

[0186] In this embodiment, two or more terminal groups as defined above are located at the ends of the estolide chain. Preferably, one or more groups R 9* Each of the general formulas -R 8 (-XC(O)-R 8 ) t More preferably, the -XC(O)-T group is selected from 2 to 27 of the formula -R 8 (-XC(O)-R 8 ) t by the group -XC(O)-T, and most preferably by 4-16 of the formula -R 8 (-XC(O)-R 8 ) t It is terminated by the group -XC(O)-T.

[0187] According to yet another preferred embodiment of the present invention, a compound represented by the general formula (VI * ) of formula (V) containing one or more moieties of - ) group-containing anions, -R 8 (-XC(O)-R 8 ) m -XC(O)-R 9* (VI * ) R in the formula 8 , R 9* and m is as defined above, or is represented by the general formula (VIII * ) containing one or more moieties of the formula (VII) - ) group-containing anions, -R 8 (-C(O)-XR 8 ) m -C(O)-XR 9* (VIII * ) R in the formula 8 , R 9* and m is as defined above; One or more groups R 9* is terminated by two or more groups, preferably 4 to 12 groups, of the structure -R 8 (-XC(O)-R 8 ) t -XC(O)-T R in the formula 8 are independently derived from C8-C24 monocarboxylic and monohydroxycarboxylic acids, in particular ricinoleic acid, 12-hydroxystearic acid, lesquerolic acid, and 11-hydroxy-undecanoic acid; X is O, and T is independently derived from C2 to C24, preferably C8 to C24, fatty acids, in particular lauric acid, myristic acid, palmitic acid, oleic acid, stearic acid, behenic acid, and arachidic acid; and t is 0-6, preferably 0, 1, 2 or 3.

[0188] According to this embodiment, preferably R 8 is derived from ricinoleic acid, and T is derived from stearic acid or oleic acid.

[0189] More preferably, all groups R 9* R 8 is derived from ricinoleic acid, and even more preferably all groups R 9* In R 8 is derived from ricinoleic acid, T is derived from stearic acid or oleic acid, and t is 0, 1, 2, or 3.

[0190] According to a further preferred embodiment of the present invention, one or more compounds represented by the following general formula (VI * ) portion of the formula (V) - ) group-containing anions, -R 8 (-XC(O)-R 8 ) m -XC(O)-R 9* (VI * ) R in the formula 8 , R 9* and m is as defined above, or represents one or more of the following general formula (VIII): *) portion of the formula (VII) - ) group-containing anions, -R 8 (-C(O)-XR 8 ) m -C(O)-XR 9* (VIII * ) R in the formula 8 , R 9* and m is as defined above; One or more groups R 9* is independently selected from one of the following branched or dendrimeric fatty acid structures: -R 14 -OC(O)-R 15 -(OC(O)-R 16 ) m1 -(OC(O)-R 17 ) m2 -OC(O)-T or -R 14 -NR 10 -C(O)-R 15 -(OC(O)-R 16 ) m1 -(OC(O)-R 17 ) m2 -OC(O)-T, During the ceremony R 10 is as defined above, R 14 is optionally -O-, -NH-, -C(O)-, -C(S)-, [ka] optionally substituted divalent hydrocarbon radicals having from 2 to 50 carbon atoms, in particular from 2 to 20 carbon atoms, more particularly from 2 to 10 carbon atoms, which may contain one or more groups selected from the group consisting of -OH or -CH, and which may be substituted by a halide group, 14must not contain a combination of -C(O)- and -O- groups or a combination of -C(O)- and -NH- or tertiary amino groups forming an internal carboxylate or amide group, and is preferably a C1-C24 n-alkylene group and a C2-C24 n-alkenylene group, in particular a -CH 2 -, -CH 2 CH 2 -, -CH 2 CH 2 CH 2 - represents R 15 are independently selected from optionally substituted linear, cyclic, or branched, substituted or unsubstituted divalent hydrocarbon radicals having up to 36 carbon atoms or C2 to C24 monocarboxylic acids having 2 to 6 hydroxy groups, e.g., 2,2'-dihydroxymethylpropanoic acid; m1 is 0 to 12, preferably 0 to 10, more preferably 0 to 6, even more preferably 1 to 6, in particular 0, 1, 2, 3, 4, 5, 6; m2 is 0 to 12, preferably 0 to 10, more preferably 0 to 6, even more preferably 1 to 6, in particular 0, 1, 2, 3, 4, 5, 6; and m1+m2 is t, where t is from 0 to 12, preferably from 0 to 10, more preferably from 0 to 6, even more preferably from 1 to 6, in particular 0, 1, 2, 3, 4, 5, 6; T is as defined above, R 16 and R 17 is defined above as R 15 is selected from the group [Table 6] Here, R 15 + The sum of the carbon atoms of T (R 15 , T's Σ carbon atom) is from 19 to 300, preferably from 25 to 300, more preferably from 35 to 300, even more preferably from 50 to 300, in particular from 35 to 200, more particularly from 35 to 150, even more particularly from 50 to 150, However, R is derived from di- or polyhydroxylated carboxylic acids. 15 , R 16 and R 17 For at least one, preferably one to two, more preferably two, even more preferably all OH groups are esterified.

[0191] According to this embodiment, one or more groups R of the anion of formula (V) or (VII) 9* are also preferably independently derived from 2,2'-dihydroxymethylpropanoic acid and dihydroxymethylpropanoic acid itself, a branched or dendrimeric fatty acid structure obtained by esterification with a C2 to C24, preferably C8 to C24, fatty acid, more preferably lauric acid, myristic acid, palmitic acid, oleic acid, stearic acid, behenic acid, arachidic acid, and optionally a monohydroxy fatty acid, in particular ricinoleic acid, as exemplified by the following structural formula: [ka] where R is: [ka] Or the structure is [ka] where R is as shown above.

[0192] Preferably, all groups R of the anion of formula (V) or (VII) 9* are independently selected from the groups of the structures set forth above.

[0193] Even more preferably, all groups R of the anion of formula (V) or (VII) 9* is represented by a single formula selected from the group of structures shown above.

[0194] Revealed here are branched or dendrimeric fatty acid structures: -R 14 -OC(O)-R 15 -(OC(O)-R 16 ) m1 -(OC(O)-R 17 ) m2 -OC(O)-T or -R 14 -NR 10 -C(O)-R 15 -(OC(O)-R 16 ) m1 -(OC(O)-R 17 ) m2 -OC(O)-T does not represent all possible substitutions of OH groups on the branched structures, but reflects the ordering of the building blocks required to satisfy the structural requirements of this embodiment.

[0195] In a preferred embodiment of the present invention, the carboxylate anion (COO - ) group-containing anions are represented by the following schematic ester structure: - O(O)C-(C1-C12 radical)-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)-(C1-C12 radical)-C(O)O - , wherein the terminal C1-C12 radical is selected from linear, branched, saturated, unsaturated or aromatic C1-C12 radicals, preferably from C2-C12, C2-C10, C2-C4 radicals, more preferably from C2 and C4 radicals.

[0196] Preferably, the C1-C12 radical and the adjacent -C(O)- group and the terminal carboxylate group are derived from acids such as malonic acid, succinic acid, adipic acid, sebacic acid, maleic acid, phthalic acid, terephthalic acid or their anhydrides, e.g. succinic anhydride, maleic anhydride and phthalic anhydride, respectively.

[0197] For example, an end group of the formula: -O(O)C-(C 2 H 4 )-C(O)- is derived from either succinic acid or succinic anhydride.

[0198] It is particularly preferred that both terminal groups of the structure are derived from the same type of dicarboxylic acid or dicarboxylic anhydride.

[0199] It should be noted that in the schematic ester structure according to this embodiment, the term "mono- or oligo-C8-C24 hydroxy fatty acid" refers to a monohydroxy fatty acid, or a hydroxy fatty acid oligomer, of the same or different kind of hydroxy fatty acid obtained by esterification, where the group "-O-" linking this moiety to the terminal group "O(O)C-(C1-C12 radical)-C(O)-" and the group "-C(O)-(O)-" linking this moiety to the central diol moiety are formally abstracted in the schematic ester structure, but are derived from the terminal -OH and terminal C(O)OH moieties of the mono- or oligohydroxy fatty acid group.

[0200] According to a further preferred embodiment of the present invention, the carboxylate anion (COO - ) group-containing anion comprises at least one moiety of the following general formula: -([-OC(O)-R 8 (-OC(O)-R 8 )lOC(O)-LC(O)-O-(R 8 -C(O)-O)lR 8 -C(O)O])- R in the formula 8is as defined above, l is independently an integer selected from 0-20, more preferably from 1-12, even more preferably from 2 to 10, and L is a divalent hydrocarbon radical having from 1 to 30 carbon atoms and optionally selected from -O-, -S-, -NH-, -C(O)-, -C(S)-, ...S-, -O-, -S-, -S-, -S-, -S-, -S-, -S-, -S-, -S-, -S-, -S-, -S-, - [ka] and quaternary ammonium groups, Preferably, L is a divalent alkylene or alkenylene radical having from 1 to 30 carbon atoms, more preferably L is selected from methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, ethenylene, propenylene, butenylene, pentenylene, hexenylene, heptenylene, octenylene, nonenylene, and most preferably L is selected from methylene, ethylene, ethenylene, or butenylene.

[0201] Preferably, the anion according to this embodiment has the general formula -([-OC(O)-R 8 (-OC(O)-R 8 )lOC(O)-LC(O)-O-(R 8 -C(O)-O)lR 8 -C(O)O])- , one part of which is as above.

[0202] As expressly noted, there may be overlap with other moieties described herein, for example overlap with the structure of the moiety of formula (VI). -R 8 (-C(O)-XR 8 ) m -C(O)-XR 9 (VI) and the general formula defined above -([-OC(O)-R 8 (-OC(O)-R 8 ) l-OC(O)-LC(O)-O-(R 8 -C(O)-O) l -R 8 -C(O)O])- It may be between.

[0203] According to the invention, the presence of a structure of the general formula -([-OC(O)-R 8 (-OC(O)-R 8 ) l -OC(O)-LC(O)-O-(R 8 -C(O)-O) l -R 8 -C(O)O])-R 9 satisfies the condition for radical G in formula (V).

[0204] According to a further preferred embodiment of the present invention, the carboxylate anion (COO - ) group-containing anion comprises at least one moiety of the following general formula: -([-OC(O)-R 8 (-OC(O)-R 8 )lOC(O)-LC(O)-O-(R 8 -C(O)-O)lR 8 -C(O)O])- where L and l are as defined above in the previous embodiment, and R 8 are independently derived from C8-C24 monocarboxylic acid-monohydroxycarboxylic acid, in particular ricinoleic acid, 12-hydroxystearic acid, lesquerolic acid, 11-hydroxy-undecanoic acid, and most preferably R 8 is derived from ricinoleic acid.

[0205] Preferably, L is selected from C1 to C10, preferably methylene, ethylene, butylene, octylene, decylene, l is independently in the range of 0 to 4, and R 8 According to another preferred embodiment of the present invention, the carboxylate anion (COO -) group-containing anion comprises at least one portion of the following structure: (fatty alcohol)-OC(O)-(mono or oligo C8-C24 hydroxy fatty acid)-OC(O)-(C2-C12 hydrocarbon)-C(O)-O-(mono or oligo C8-C24 hydroxy fatty acid)-C(O)-O-(fatty alcohol).

[0206] wherein the C2-C12 hydrocarbon is a C2-C12 hydrocarbylene group, in particular derived from succinic acid, maleic acid, itaconic acid, adipic acid, sebacic acid, dodecanoic diacid, the mono- or oligo-C8-C24 hydroxy fatty acid is a group derived from a C8-C24 hydroxy-substituted carboxylic acid monomer or an oligomer formed by esterification from up to 20 C8-C24 hydroxy-substituted carboxylic acid monomers, in particular derived from monoricinoleic acid or oligoricinoleic acid having an oligomer degree of 2 to 20, preferably 2 to 10, more preferably 2 to 6, even more preferably 2 to 4, and the fatty alcohol is a group derived from a C2 to C24, preferably C8 to C24, fatty alcohol, in particular derived from n-octanol, n-decanol, n-dodecanol, n-tetradecanol, n-hexadecanol, oleyl alcohol, stearyl alcohol, behenyl alcohol, arachidyl alcohol.

[0207] This class of compounds is exemplified by the following structure: [ka] Here, R 1 teeth: [ka] (The dotted bonds are R 1 R for the O atom in the upper structure 1 (showing the bond).

[0208] In a further preferred embodiment according to the present invention, the carboxylate anion (COO - ) group-containing anion comprises at least one portion of the following structure: -([-OC(O)-R 8 (-OC(O)-R 8 ) l -OC(O)-LC(O)-O-(R 8 -C(O)-O) l -R 8 -C(O)O])-R 9 In the formula L, l, R 8 and R 9 is as defined above.

[0209] Preferably, L, l and R 8 is as defined above, and R 9 is selected from C1-C23 hydrocarbyl groups, preferably C1-C18 hydrocarbyl groups, more preferably C7-C19 hydrocarbyl groups, even more preferably C11-C17 hydrocarbyl groups, and most preferably derived from lauric acid, myristic acid, palmitic acid, oleic acid, and stearic acid.

[0210] More preferably, the compound of formula (V) has the structure R 9 -([-OC(O)-R 8 (-OC(O)-R 8 ) l -OC(O)-LC(O)-O-(R 8 -C(O)-O) l -R 8 -C(O)O])-R 9 In the formula, L, l and R 8 is as defined above, and R 9are independently selected from C1-C23 hydrocarbyl groups, preferably C1-C18 hydrocarbyl groups, more preferably C7-C19 hydrocarbyl groups, even more preferably C11-C17 hydrocarbyl groups, and most preferably derived from lauric acid, myristic acid, palmitic acid, oleic acid, and stearic acid.

[0211] Even more preferably, L is selected from methylene, ethylene or ethenylene, butylene, hexylene, octylene, decylene, or derived from itaconic acid; l is independently selected from the range of 0 to 4; R 8 is selectively derived from ricinoleic acid, and R 9 is selectively derived from oleic acid or stearic acid.

[0212] In an even more preferred embodiment of the present invention, the carboxylate anion (COO - ) group-containing anion includes at least one moiety of the following formula: R 1* [(-OC(O)-R 8 ) m -OC(O)-] 2 R in the formula 1* is a divalent C1-C100 radical, preferably a C1-C12 alkylene, most preferably a methylene, ethylene, 1,3-propylene, 1,4-butylene, 1,6-hexylene, 1,2-propylene, 1,3-butylene radical; m is independently selected from 1 to 12, and R 8 is as defined above.

[0213] In this case, the part of the formula R 1* [(-OC(O)-R 8 ) m -OC(O)-] 2 is preferably formed by successive or block-by-block ester chain formation starting from an alkylene diol, more preferably an α,ω-alkylene diol, such as 1,2-ethanediol, 1,3-propanediol, 1,4-butanediol and 1,6 hexanediol.

[0214] Whether a single hydroxy-substituted carboxylic acid is added repeatedly or an estolide chain bearing a carboxylic acid group is made to react with such a diol, the use of an excess of carboxylic acid reactant results in a product in which the diol is primarily esterified in the same manner at both ends, i.e., the symmetrical structure of the formula R 1* [(-OC(O)-R 8 ) m -OC(O)-] 2 The formation of

[0215] base R 1* The structure of thus corresponds directly to the alkylene diols usually applied as starting materials.

[0216] According to the present invention, R 1* is a divalent C2-C100 hydrocarbon radical, which includes all types of straight chain, branched chain, and cyclic aliphatic and aromatic divalent hydrocarbon groups, such as alkylene, alkenylene, alkynylene, and aromatic structures, such as phenylene.

[0217] Since C1-C12 alkylene diols are the preferred starting materials, R 1* is preferably a C1-12 alkylene group, more preferably a 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.

[0218] According to this embodiment, m is independently selected, but preferably both m in the following general formula are equal: R 1*[(-OC(O)-R 8 ) m -OC(O)-] 2 because this part is typically symmetrical.

[0219] More preferably, m is independently selected from 1-6, more preferably from 1-4, even more preferably, both m are the same and selected from 1-6, and most preferably, both m are the same and selected from 1-4.

[0220] According to this embodiment, R 8 is as defined above, but preferably R 8 Radicals are straight-chain alkylene and alkenylene groups, in particular straight-chain 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 straight-chain C6-C24 alkenylene groups, such as For example, hexenylene, heptenylene, octenylene, nonenylene, decenylene, undecenylene, dodecenylene, tridecenylene, tetradecenylene, pentadecenylene, hexadecenylene, heptadecenylene, octadecenylene, nonadecenylene, eicosenylene, henicosenylene, doicosenylene, tricosenylene, tetraicosenylene, where these groups are most preferably bonded via a terminal carbon atom to the adjacent C(O) group.

[0221] More preferably, R 8 is derived from a C7-C25 fatty acid bearing one hydroxyl group as a substituent, and even more preferably R 8 is derived from ricinoleic acid, lesquerolic acid, 10-hydroxyoctadecanoic acid, 12-hydroxyoctadecanoic acid, 14-hydroxytetradecanoic acid, 10-hydroxystearic acid, and 12-hydroxystearic acid.

[0222] Most preferably R 8 is derived from ricinoleic acid.

[0223] Generally preferred in this embodiment are moieties of the general formula R 1* [(-OC(O)-R 8 ) m -OC(O)-] 2 All R 8 The base is the same.

[0224] In a particularly preferred embodiment of the present invention, in at least one moiety of the general formula R 1* [(-OC(O)-R 8 ) m -OC(O)-] 2 R 1* is selected from methylene, ethylene, 1,3-propylene, 1,4-butylene, 1,6-hexylene, 1,2-propylene, and 1,3-butylene; R 8 is derived from a C8-C24 monocarboxylic acid-monohydroxycarboxylic acid, in particular ricinoleic acid, 12-hydroxystearic acid, lesquerolic acid, 11-hydroxy-undecanoic acid, and m is independently selected from 1 to 6.

[0225] The present application is further directed to another embodiment of the present invention, which is a process for the preparation of the inventive organic ammonium salt according to any of the above-mentioned embodiments according to the invention described herein.

[0226] The process for producing an organic ammonium salt according to the present invention comprises: (i) a compound comprising an organic amine corresponding to an organic ammonium group-containing cation and a carboxylate anion (COO - ) group-containing anion with the corresponding carboxylic acid (-COOH); or (ii) a salt of an inorganic anion containing organic ammonium group-containing cation and a carboxylate anion (COO - ) group-containing anion with a metal salt of the corresponding carboxylic acid (-COOH); or (iii) a hydroxy salt of an organic ammonium group-containing cation and a carboxylate anion (COO - ) group-containing anions with the corresponding carboxylic acids.

[0227] In alternative (i) an ammonium cation and a carboxylate anion are formed by the transfer of a proton from the carboxylic acid to the organic amine, and therefore no further products are formed in the reaction, whereas in the process of alternative (ii) one equivalent of a salt of a metal cation and an inorganic anion is formed, such as an alkali metal or alkaline earth metal halide, in particular NaCl, KCl, NaBr, NaCl, NaI, and KI, and in alternative (iii) one equivalent of water is formed when obtaining the organic ammonium salt according to the invention.

[0228] Thus, in the organic ammonium salts obtained by process alternatives (ii) and (iii), all of the ammonium groups may be quaternary ammonium moieties, whereas the ammonium salts of the invention obtained by process alternative (i) contain at least one tertiary, secondary or primary ammonium moiety.

[0229] In alternative (ii) according to this embodiment, an ammonium salt having an inorganic anion is applied to form an organic ammonium salt according to the invention, wherein the term "inorganic anion" is - halide anions, in particular fluoride, chloride, bromide and iodide anions, hydroxyl anions, hydrosulfide anions, anions formed as conjugate bases of inorganic oxoacids, such as, for example, anions of chlorate, chlorite, iodate, nitrate, nitrite, perchlorate, phosphate, sulfate or sulfite, in particular the anions of phosphate and sulfate, - refers to inorganic oxoacid ester anions, for example sulfate ester anions such as methyl sulfate, and phosphate ester anions such as monomethyl phosphate and dimethyl phosphate.

[0230] In a preferred embodiment according to the present invention, the process for the preparation of organic ammonium salts comprises an anion exchange reaction step (ii) in which a carboxylate anion (COO) selected from the group consisting of formulae (V), (VII) and (X) is reacted with an anion exchange reaction step (ii) in which ... - In the present invention, an alkali metal salt or an alkaline earth metal salt of a carboxylic acid (-COOH) corresponding to the aryl group-containing anion is applied.

[0231] Therein, the Li, Na, K, Mg and Ca salts are preferred, and most preferably the carboxylate salt is a Na or K salt.

[0232] In another preferred embodiment according to the present invention, the preparation of the organic ammonium salt according to the present invention comprises the steps of: (ii) reacting an inorganic anion-containing salt of an organic ammonium group-containing cation with a carboxylate anion (COO) selected from the group consisting of formulae (V), (VII) and (X): - (VII) group-containing anion with a metal salt of a corresponding carboxylic acid (-COOH), wherein the carboxylate anion (COO) is selected from the group consisting of formulas (V), (VII) and (X): - A Na or K carboxylate containing an ammonium group-containing anion is contacted with an inorganic anion-containing salt of an organic ammonium group-containing cation selected from primary, secondary, tertiary, and quaternary amine salts containing chloride, bromide, or methosulfate anions.

[0233] Usually, the inorganic anion of the organic ammonium salt is derived from the formation of the salt by substitution reaction between the amine and an organic compound carrying a leaving group, such as an iodo, bromo, chloro, mesylate or tosylate leaving group. In this embodiment, the use of inorganic anion-containing salts containing chloride, bromide or methosulfate anions is preferred. Most preferably, amine salts with chloride or bromide anions are applied.

[0234] According to a further preferred embodiment of the present invention, in the process according to the present invention, the anion exchange reaction (ii) leading to the target salt compound according to any of the embodiments according to the present invention is carried out in a separate reaction step, prior to any contact with other ingredients of the final cosmetic formulation.

[0235] Here, according to the present invention, the term "other ingredients of the final cosmetic formulation" includes all components of the cosmetic formulation composition except water and the salt formed as a by-product in step (ii), i.e. according to this embodiment, the ammonium salt compound may be added to the cosmetic formulation as an aqueous solution, optionally also containing the salt formed as a by-product in reaction (ii).

[0236] In yet another preferred embodiment of the present invention, in the process according to the invention, a carboxylate anion (COO - Alkali salts of carboxylic acids (-COOH) corresponding to the ) group-containing anions are added to partial or complete cosmetic formulations containing primary, secondary, tertiary, and quaternary amine salts with inorganic counterions.

[0237] Preferably, the alkali salts of carboxylic acids are selected from sodium and potassium salts.

[0238] In accordance with this embodiment, the organic ammonium salt according to the present invention is formed partially or completely in the cosmetic formulation, where a salt of an alkali metal cation and an inorganic anion are formed as by-products.

[0239] According to another preferred embodiment of the present invention, the process for producing an organic ammonium salt according to any of the embodiments of the present invention comprises the anion exchange reaction step (iii) described above, in which a carboxylate anion (COO) selected from the group consisting of formulas (V), (VII) and (X) is reacted with an anion exchange reaction step (iii) of the present invention. - The anion exchange reaction step (iii), in which the carboxylic acid corresponding to the ) group-containing anion is contacted with primary, secondary, tertiary amine and quaternary ammonium ions having OH- counterions, is carried out in a separate reaction step prior to any contact with other components of the final cosmetic formulation.

[0240] Here, according to this embodiment, the term "other ingredients of the final cosmetic formulation" includes all components of the cosmetic formulation composition except water, i.e., according to this embodiment, the ammonium salt compound may be added to the cosmetic formulation as an aqueous solution.

[0241] According to yet another preferred embodiment of the present invention, the process for the preparation of an organic ammonium salt according to any of the embodiments of the present invention comprises the anion exchange reaction step (iii) described above, in which a carboxylate anion (COO) selected from the group consisting of formulas (V), (VII) and (X) is reacted with an anion exchange reaction step (iii) - A carboxylic acid corresponding to the OH-group-containing anion is added to and contacted with a partial or complete cosmetic formulation containing a primary, secondary, tertiary, or quaternary amine salt having an OH- counterion.

[0242] According to this embodiment, the organic ammonium salt according to the present invention is formed in a partial or complete cosmetic formulation, where one equivalent of water is formed as a by-product.

[0243] Another embodiment of the present invention is the use of a compound according to the invention as defined in any of the above embodiments in cosmetic formulations for skin care and hair care such as conditioners and shampoos.

[0244] According to preferred embodiments of the invention, the salt compounds of any of the above mentioned embodiments are used in cosmetic formulations for skin care and hair care such as conditioners and shampoos, in particular conditioners and shampoos, abrasives for treating and coating hard surfaces, e.g. in formulations for drying automobiles and other hard surfaces after washing, for finishing textiles and textile fibers, as separate softeners after textiles have been washed with nonionic or anionic / nonionic detergent formulations, as softeners in nonionic or anionic / nonionic surfactant based formulations for washing textiles, and as a means for preventing or removing wrinkles in textiles.

[0245] As shown in the examples, the organic ammonium salts according to the invention show a clear conditioning effect on fabrics and can thus be used in a beneficial manner in applications according to this embodiment. When a formulation comprising an organic ammonium salt according to the invention is applied to a hard surface as described above, a hydrophobic coating is formed.

[0246] In a further preferred embodiment of the invention, the salt compound of any of the embodiments according to the invention is used in a cosmetic composition for the treatment of textiles, preferably amino acid based textiles, more preferably human hair, particularly useful for hair color retention, hair shine enhancement, hair color enhancement, hair color protection, hair conditioning, hair smoothing or softening, improving hair manageability, especially improving hair combability.

[0247] The organoammonium salt compounds according to the invention can be used in the manner defined in this embodiment due to their distinct conditioning properties.

[0248] In another embodiment, the present invention is directed to a hair treatment composition comprising a salt compound as defined in any embodiment according to the present invention.

[0249] In a preferred embodiment according to the present invention, the hair treatment composition comprising the salt compound of any of the embodiments according to the present invention is selected from the group consisting of hair shampoo compositions, hair conditioner compositions, hair color or hair dye compositions, hair combing compositions, hair rinse-off and leave-on compositions.

[0250] In still a further embodiment, the present invention is also directed to the use of the product obtained by the process defined in the above-mentioned embodiment of the present invention.

[0251] In a preferred embodiment according to the present invention, the product obtained by the process defined in the above mentioned embodiment of the present invention is used in cosmetic formulations for skin care and hair care such as conditioners and shampoos, in particular conditioners and shampoos, abrasives for treating and coating hard surfaces, for example in formulations for drying automobiles and other hard surfaces after car washing, for finishing textiles and textile fibres, as a separate softening agent after textiles have been washed with nonionic or anionic / nonionic detergent formulations, as a softening agent in formulations based on nonionic or anionic / nonionic surfactants for washing textiles, and as a means for preventing or removing wrinkles in textiles.

[0252] According to a further preferred embodiment of the present invention, the product obtained by the process defined in the above mentioned embodiment of the present invention is used in a cosmetic composition for the treatment of textiles, preferably amino acid based textiles, more preferably human hair, in particular for hair colour retention, hair shine enhancement, hair colour enhancement, hair colour protection, hair conditioning, hair smoothing or softening, improving hair manageability, in particular improving hair combability.

[0253] Finally, in another embodiment, the present invention is directed to a composition for treating hair, comprising a salt compound obtained by the process defined in the above-mentioned embodiment of the present invention.

[0254] In a preferred embodiment of the present invention, the composition for the treatment of hair comprising the salt compound obtained by the process defined in the above-mentioned embodiment of the present invention is selected from the group consisting of hair shampoo compositions, hair conditioner compositions, hair colour or hair dye compositions, hair combing improving compositions, hair rinse-off and leave-on compositions. EXAMPLES

[0255] (Unless otherwise stated, percentages are by weight.) As used herein, the term "castor oil" generally refers to ricinoleic acid triglyceride.

[0256] A Note on the Terminology Used in This Application for Estolide Moieties and Estolide Compounds The nomenclature used to depict the structure of the estolide group in the following examples indicates that the estolide moiety is at least formally derived from an esterification compound, and the carboxylic acids from which the estolide moiety is at least formally derived are shown in order within parentheses. When several subunits derived successively from the same acid are present in the estolide moiety, they are shown within parentheses with an integer subscript indicating the number of repeating units, and the entire carboxylic acid is shown within square brackets.

[0257] It should be noted that the specific carboxylic acids shown in parentheses or brackets are not combined into a random structure, but rather have the exact order of each of the hydroxyl carboxylic acid derived residues and carboxylic acid derived residues as indicated in the terminology used, where the last carboxylic acid given in each term in parentheses or brackets is the terminal carboxylic acid of the estolide moiety, and the order of the carboxylic acid residues linked by the ester groups from the beginning of the parenthetical or bracketed term to the end of the term is indicated in the exact order and number of residues involved.

[0258] For example, the term "(12-hydroxystearic acid-ricinoleic acid-oleic acid)" refers to an estolide moiety in which a 12-hydroxystearic acid molecule is formally linked to a carboxylic acid group of a ricinoleic acid molecule by forming an ester group through its OH group. The hydroxyl group of the ricinoleic acid group is linked to the oleic acid molecule by forming an ester group with the carboxylic acid group of the oleic acid molecule. The oleic acid in this example is considered the terminal group of this particular estolide moiety because if the estolide moiety is a substituent of a higher order structure (i.e., a more complex molecule), the estolide moiety is generally linked to the overall structure via a link to the carboxylic acid group of the first mentioned residue in the terminology used for the estolide moiety. In this case, it is the first mentioned 12-hydroxystearic acid residue, and the oleic acid residue is the terminal group of the estolide moiety.

[0259] Thus, when the terminology used refers to a carboxylic acid chloride of an estolide structure, the first listed carboxylic acid residue in parentheses, i.e., the residue furthest from the terminal group, necessarily forms the acyl chloride group.

[0260] When the term "dimer" or "trimer" etc. is used, it refers to the number of subunits derived from the carboxylic acid of the estolide portion.

[0261] Similarly, the term "(ricinoleic acid) 2"Ricinoleic acid [1-oleic acid] estolide" formally refers to an estolide moiety or compound in which a ricinoleic acid molecule or residue is linked via its OH group to the carboxylic acid group of another ricinoleic acid molecule by forming an ester group. The hydroxyl group of this latter ricinoleic acid group is linked to the oleic acid molecule by forming an ester group with the carboxylic acid group of the oleic acid molecule. The oleic acid is considered to be the terminal group of this particular estolide moiety because if the estolide moiety is a substituent of a higher order structure (i.e., a more complex molecule), the estolide moiety is linked to the overall structure via a link to the carboxylic acid group of the first-mentioned ricinoleic acid residue, and the oleic acid residue becomes the terminal group of the estolide moiety.

[0262] The estolide portion is [(ricinoleic acid) 6 -Succinic acid-(ricinoleic acid) 6 When the carboxylic acid residues are linked by an ester or amide linking group, such as the succinic acid derived residue linked by an ester group on each side to two ricinoleic acid estolide residues in [1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56], this is indicated by incorporating the name of the parent compound into the terminology of the overall estolide structure, thus providing an easily understood terminology indicating the order of the carboxylic acid residues.

[0263] It is further noted that the precise structures of the estolides are primarily revealed by the structural formulae provided in detail for the exemplary compounds, and the structures of the exemplary compounds are also clearly derivable by those skilled in the art from the detailed experimental procedures presented, particularly for reasons of simplification, where the formulae do not always reflect the stoichiometrically precise structures.

[0264] Working Example Synthesis Example 1 Synthesis of (ricinoleic acid-oleic acid) estolide dimer

[0265] In a 1000 ml 4-necked bottle equipped with a reflux condenser, a thermometer and a magnetic stirrer, a dropping funnel and a gas outlet, 225 g (0.75 mol) of ricinoleic acid was placed at room temperature under nitrogen. With stirring, 226.85 g (0.75 mol) of oleic acid chloride was added slowly during 1.5 hours. The temperature was increased from 22 to 32°C. This increase in temperature was accompanied by the formation of gas bubbles, indicating the formation of HCl. The temperature was kept at 32°C for a further 2 hours, then increased to 50°C and held there for 1 hour. The volatiles were removed under reduced pressure (40°C / 2 hours / 20 mmHg). The conversion of OH groups was 1 The conversion of the OH groups was 100%, as determined by H NMR spectroscopy.

[0266] A brownish clear oil was obtained having essentially the following structure: [ka] [ka]

[0267] The corresponding estolide carboxylate anion is encompassed by formula (X): R 7 (-C(O)-XR 8 -COO - ) q where X=O and q=1, and R 8 (emphasis): [ka] R 7 (emphasis): [ka]

[0268] Synthesis Example 2 [(Ricinoleic acid) 2Synthesis of Estolide Trimers

[0269] In a 250 ml 4-necked bottle equipped with a reflux condenser, a thermometer, a magnetic stirrer, a dropping funnel and a gas exhaust tube, 34.87 g (0.293 mol) of SOCl 2 was placed under nitrogen atmosphere at room temperature. With stirring, 110 g (0.195 mol) of the estolide dimer of Synthesis Example 1 was added slowly during 1 hour. After the addition was complete, the temperature was raised to 80° C. The temperature was held at 80° C. for 1 hour. The volatiles were removed under reduced pressure (80° C. / 2 hours / 20 mmHg). The vacuum was broken with nitrogen and 57.75 g (0.195 mol) of ricinoleic acid was added to the carboxylic acid chloride intermediate at 80° C. over 45 minutes. The temperature was held for 2 hours. The volatiles were removed under reduced pressure (40° C. / 2 hours / 20 mmHg). The conversion of OH groups was 1 The conversion of the OH groups was 100%, as determined by H NMR spectroscopy.

[0270] A brownish clear oil was obtained having essentially the following structure: [ka]

[0271] Example 2a [(Ricinoleic acid) 2 Synthesis of Estolide Trimer of [-Stearic Acid]

[0272] Two 250 ml three-necked bottles A and B, equipped with a reflux condenser, a thermometer and a magnetic stirrer, a dropping funnel and a gas outlet, were flushed with nitrogen. Bottle A was used to react fatty acid chloride with ricinoleic acid to produce chain-extended fatty acid esters. Then, SOCl 2 Bottle B was used to react the resulting fatty acid ester chloride with ricinoleic acid to give the chain-extended fatty acid ester. 2Addition of ricinoleic acid to the flask gave the corresponding fatty acid ester chloride, which was transferred back to bottle A and reacted with fresh ricinoleic acid. The above cycle can be repeated to obtain the estolide [(ricinoleic acid) 5 -stearic acid] hexamer may be prepared.

[0273] General procedure for the synthesis of chain extended fatty acid esters: The calculated amount of ricinoleic acid is placed in a bottle. An equimolar amount of fatty acid ester chloride is slowly added at room temperature. To complete the reaction, the temperature is increased to 80°C for 3 hours. The complete conversion of OH groups is 1 Determined by 1 H NMR spectroscopy.

[0274] General procedure for the synthesis of fatty acid ester chlorides: Add the calculated amount of fatty acid ester to the bottle. 2 (3-fold molar excess) is slowly added at room temperature. The mixture is then heated to 80° C. This temperature is maintained for 3 hours. Excess SOCl 2 The benzene is removed under reduced pressure (80°C / 2 hours / 20 mmHg). Complete conversion of C(O)OH groups to C(O)Cl groups is observed. 1 Determined by 1 H NMR spectroscopy.

[0275] The table below summarizes the materials and amounts used. [Table 7]

[0276] [(Rishi) 2 -stearic acid] has the following formula: [ka]

[0277] Example 2b Synthesis of (ricinoleic acid-12-hydroxystearic acid-oleic acid) estolide trimer

[0278] The procedure outlined for synthesis example 2a was repeated.

[0279] The table below summarizes the materials and amounts used. [Table 8]

[0280] The formula for lysyl-(12-hydroxystearic)-oleic acid is: [ka]

[0281] Example 2c Synthesis of (12-hydroxystearic acid-ricinoleic acid-oleic acid) estolide trimer

[0282] The procedure outlined for synthesis example 2a was repeated.

[0283] The table below summarizes the materials and amounts used. [Table 9]

[0284] The formula for (12-hydroxystearic-acid) is: [ka]

[0285] Synthesis Example 3 [(Ricinoleic acid) 5 -oleic acid] estolide hexamers and the corresponding [(ricinoleic acid) 5 Synthesis of hexamer of [-oleic acid] chloride

[0286] Two 100 ml three-necked bottles A and B, equipped with a reflux condenser, a thermometer and a magnetic stirrer, a dropping funnel and a gas outlet, were flushed with nitrogen. Bottle A was used to react fatty acid chloride with ricinoleic acid to produce chain-extended fatty acid esters. Then, SOCl 2 Bottle B was used to react the resulting fatty acid ester chloride with ricinoleic acid to give the chain-extended fatty acid ester. 2 Addition of ricinoleic acid to bottle A gave the corresponding fatty acid ester chloride, which was transferred back to bottle A and reacted with fresh ricinoleic acid. The above cycle was repeated to obtain the estolide [(ricinoleic acid) 5 -oleic acid] hexamer was prepared.

[0287] General procedure for the synthesis of chain extended fatty acid esters: A calculated amount of ricinoleic acid is placed in a bottle. An equimolar amount of fatty acid ester chloride is slowly added at room temperature. To complete the reaction, the temperature is raised to 80°C for 3 hours. Complete conversion of the OH group of ricinoleic acid to an ester is observed. 1 Determined by 1 H NMR spectroscopy.

[0288] General procedure for the synthesis of fatty acid ester chlorides: Add the calculated amount of fatty acid ester to the bottle. 2 (3-fold molar excess) is slowly added at room temperature. The mixture is then heated to 80° C. This temperature is maintained for 3 hours. Excess SOCl 2 The complete conversion of C(O)OH groups to C(O)Cl groups is achieved by removing the amine group under reduced pressure (80°C / 2 hours / 20 mmHg). 1 Determined by 1 H NMR spectroscopy.

[0289] The table below summarizes the materials and amounts used. [Table 10]

[0290] Essentially the following structure [(Rishi) 5 -oleic acid] was obtained. [ka]

[0291] Corresponding [(Rishi) 5 -oleic acid chloride has the following structure: [ka]

[0292] Synthesis Example 4 Branched bis-[(ricinoleic acid) based on bis-2,2-dihydroxymethylpropionic acid 2 Synthesis of estolides containing 1-oleic acid

[0293] In a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, a magnetic stirrer, a dropping funnel and a gas exhaust tube, 48.88 g (0.0567 mol) of [(ricinoleic acid) 2 [-oleic acid] chloride was mixed with 3.80 g (0.0284 mol) of 2,2-dihydroxymethylpropionic acid. The mixture was heated to 100°C for 8 h. Volatiles were removed under reduced pressure (80°C / 1 h / 20 mmHg). Complete conversion of the OH groups of 2,2-hydroxymethylpropionic acid was observed. 1 Determined by 1 H NMR spectroscopy.

[0294] A brownish clear oil was obtained having essentially the following structure: [ka] Where R = [ka]

[0295] Example 4a Bis-[(ricinoleic acid) 2 Synthesis of [-oleic acid]estolide dendrimers

[0296] In a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, a magnetic stirrer, a dropping funnel and a gas outlet tube, the branched bis-[(ricinoleic acid) 2 64.57 g (0.03617 mol) of [-oleic acid] estolide was heated to 80 ° C. 8.61 g (0.0723 mol) of SOCl 2 was added within 10 min. The reaction was maintained for 4 h. The volatiles were removed under reduced pressure (80° C. / 1 h / 20 mmHg). Complete conversion of C(O)OH groups to C(O)Cl groups was observed. 1 The reaction temperature was determined by H NMR spectroscopy. 2.42 g (0.01808 mol) of 2,2-dihydroxymethylpropionic acid was added at 80° C. and the reaction was maintained for another 5 h. The volatiles were removed under reduced pressure (80° C. / 0.5 h / 20 mmHg). Complete conversion of the terminal OH groups of bis-2,2-dihydroxymethylpropionic acid was observed. 1 Determined by 1 H NMR spectroscopy.

[0297] A viscous brownish clear oil was obtained having essentially the following dendrimer structure: [ka] Where R = [ka]

[0298] Example 4b Branched bis-[(ricinoleic acid) based on 2,2-dihydroxymethylpropionic acid 2 Synthesis of estolide [stearic acid]

[0299] In a 250 ml three-necked bottle equipped with a reflux condenser, a thermometer, a magnetic stirrer, a dropping funnel and a gas exhaust tube, 95.06 g (0.1124 mol) of [(ricinoleic acid) 2 -stearic acid] estolide was heated to 80 ° C. 33.8 g (0.28 mol) of SOCl 2 was added within 10 min. The reaction was maintained for 4 h. Volatiles were removed under reduced pressure (80° C. / 1 h / 20 mmHg). Complete conversion of C(O)OH groups to C(O)Cl groups was observed. 1 Determined by 1 H NMR spectroscopy.

[0300] In a 250 ml three-necked bottle equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel and gas exhaust, 92.88 g (0.1075 mol) of (ricinoleic acid) 2 The stearic acid chloride intermediate and 7.22 g (0.0538 mol) of 2,2-dihydroxymethylpropionic acid were mixed at 80° C. and the reaction was maintained for another 5 hours. The volatiles were removed under reduced pressure (80° C. / 0.5 h / 20 mmHg). Complete conversion of the OH groups of 2,2-dihydroxymethylpropionic acid was observed. 1 Determined by 1 H NMR spectroscopy.

[0301] A viscous brownish clear oil was obtained having essentially the following structure: [ka] Where R = [ka]

[0302] Example 4c Synthesis of branched bis-(ricinoleic acid-12-hydroxystearic acid-oleic acid) estolides based on 2,2-dihydroxymethylpropionic acid

[0303] In a 250 ml three-necked bottle equipped with a reflux condenser, a thermometer, a magnetic stirrer, a dropping funnel and a gas outlet, 102.95 g (0.1218 mol) of the (ricinoleic acid-12 hydroxystearic acid-oleic acid) estolide of Synthesis Example 2b was heated to 80° C. 42.8 g (0.36 mol) of SOCl 2 was added within 10 min. The reaction was maintained for 4 h. Volatiles were removed under reduced pressure (80° C. / 1 h / 20 mmHg). Complete conversion of C(O)OH groups to C(O)Cl groups was observed. 1 Determined by 1 H NMR spectroscopy.

[0304] In a 250 ml 3-necked bottle equipped with a reflux condenser, thermometer and magnetic stirrer, dropping funnel and gas outlet, 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 2,2-dihydroxymethylpropionic acid were mixed at 80° C. and the reaction was maintained for another 5 hours. Volatiles were removed under reduced pressure (80° C. / 0.5 hours / 20 mmHg). Complete conversion of OH groups from 2,2-dihydroxymethylpropionic acid was observed. 1 Determined by 1 H NMR spectroscopy.

[0305] A viscous brownish clear oil was obtained having essentially the following structure: [ka] Where R = [ka]

[0306] Example 4d Synthesis of branched (12-hydroxystearic-ricinoleic-oleic) estolides based on 2,2-dihydroxymethylpropionic acid

[0307] In a 250 ml three-necked bottle equipped with a reflux condenser, a thermometer, a magnetic stirrer, a dropping funnel and a gas outlet, 98.05 g (0.116 mol) of the (12-hydroxystearic acid-ricinoleic acid-oleic acid) estolide of Synthesis Example 2c was heated to 80° C. 30.08 g (0.25 mol) of SOCl 2 was added within 10 min. The reaction was maintained for 4 h. Volatiles were removed under reduced pressure (80° C. / 1 h / 20 mmHg). Complete conversion of C(O)OH groups to C(O)Cl groups was observed. 1 Determined by 1 H NMR spectroscopy.

[0308] In a 250 ml three-necked bottle equipped with a reflux condenser, thermometer and magnetic stirrer, dropping funnel and gas outlet, 97.4 g (0.1127 mol) of (12-hydroxystearic acid-ricinoleic acid-oleic acid) chloride intermediate and 7.56 g (0.0564 mol) of 2,2-dihydroxymethylpropionic acid were mixed at 80° C. and the reaction was maintained for another 5 h. The volatiles were removed under reduced pressure (80° C. / 0.5 h / 20 mmHg). Complete conversion of the OH groups of the hydroxymethyl groups was observed. 1 Determined by 1 H NMR spectroscopy.

[0309] A viscous brownish clear oil was obtained having essentially the following structure: [ka] Where R = [ka]

[0310] Synthesis Example 5 Alpha-branched bis-[(ricinoleic acid) based on 2,2-dihydroxymethylpropionic acid 5 Synthesis of estolides containing 1-oleic acid

[0311] In a 100 ml three-necked bottle equipped with a reflux condenser, a thermometer, a magnetic stirrer, a dropping funnel and a gas exhaust tube, 29.53 g (0.0173 mol) of [(ricinoleic acid) 5 [-oleic acid] chloride was mixed with 1.16 g (0.00866 mol) of 2,2-dihydroxymethylpropionic acid. The mixture was heated at 105°C for 5 h. Volatiles were removed under reduced pressure (80°C / 10 min / 20 mmHg). Complete conversion of the OH groups of 2,2-dihydroxymethylpropionic acid was observed. 1 Determined by 1 H NMR spectroscopy.

[0312] A brownish clear oil was obtained having essentially the following structure: [ka] Where R = [ka]

[0313] Synthesis Example 6 [(Ricinoleic acid) 6 -Succinic acid-(ricinoleic acid) 6 Synthesis of diacid estolides

[0314] Two 250 ml three-necked bottles A and B equipped with reflux condenser, thermometer and magnetic stirrer, dropping funnel and gas outlet were flushed with nitrogen. Bottle A was used to react the starting dicarboxylic acid succinic acid dichloride or fatty acid chloride with ricinoleic acid to produce the chain-extended fatty acid esters. Subsequent addition of SOCl2 gave the corresponding fatty acid ester chlorides.

[0315] Bottle B was used to react the resulting fatty acid ester chloride with ricinoleic acid to give the chain-extended fatty acid ester. Subsequent addition of SOCl2 gave the corresponding fatty acid ester chloride. This fatty acid chloride was transferred back to Bottle A to react with fresh ricinoleic acid. The above cycle can be used to produce estolides [(ricinoleic acid) 6 -Succinic acid-(ricinoleic acid) 6 This was repeated until a solution of 100% ethanol was prepared.

[0316] General procedure for the synthesis of chain extended fatty acid esters: The calculated amount of ricinoleic acid is placed in a bottle. An equimolar amount of fatty acid ester chloride is slowly added at room temperature. To complete the reaction, the temperature is raised to 80°C for 3 hours. Complete conversion of OH groups to esters is observed. 1 Determined by 1 H NMR spectroscopy.

[0317] General procedure for the synthesis of fatty acid ester chlorides: Add the calculated amount of fatty acid ester to the bottle. 2 (3-fold molar excess) is slowly added at room temperature. The mixture is then heated to 80° C. This temperature is maintained for 3 hours. Excess SOCl 2 The complete conversion of C(O)OH groups to C(O)Cl groups is achieved by removing the amine group under reduced pressure (80°C / 2 hours / 20 mmHg). 1 Determined by 1 H NMR spectroscopy.

[0318] The table below summarizes the materials and amounts used. [Table 11]

[0319] Essentially the following structure [(Rishi) 6 -Succinic acid-(lysine) 6 A brownish clear oil was obtained having the following structure: [ka]

[0320] Synthesis Example 7 Synthesis of castor oil-based estolides bearing succinic acid monoester moieties

[0321] In a 100 ml 3-necked bottle equipped with a reflux condenser, thermometer, magnetic stirrer, dropping funnel and gas outlet, x g of castor oil was mixed with x g of succinic anhydride and x g of Et3N catalyst. The mixture was heated to 105°C for 5 hours. Complete conversion of the anhydride ring and the formation of the ester bond was confirmed by 1 1 H NMR spectroscopy.

[0322] 29.53 g (0.0173 mol) of ricinoleic acid-oleic acid dimer chloride (intermediate of Synthesis Example 2) was added. The mixture was heated to 105° C. for 5 hours. Volatiles were removed under reduced pressure (80° C. / 10 min / 20 mmHg). Complete conversion of the —C(O)Cl groups and simultaneous formation of the ester bond were observed. 1 Determined by 1 H NMR spectroscopy.

[0323] A brownish clear oil was obtained having essentially the following structure: [ka] Here, one R = [ka] And the remaining two R groups = [ka]

[0324] Synthesis Example 8 Synthesis of hexa-tertiary amines based on glycerol diglycidyl ether.

[0325] In a 100 mL three-necked bottle equipped with a reflux condenser, thermometer, and mechanical stirrer, 0.22 g (0.0016 moles of epoxy groups; specific epoxy content is 0.00729 moles of epoxy groups / g) of glycerin diglycidyl ether, 0.30 g (0.0016 moles of NH groups) of (CH 3 ) 2 NCH 2 CH 2 CH 2 NHCH 2 CH 2 CH 2 N(CH 3 ) 2 and 55 g of 2-propanol were mixed at room temperature. The mixture was heated at 80° C. for 8 hours. Complete conversion of the epoxy groups was 1 Confirmed by 1 H NMR spectroscopy.

[0326] A brownish liquid was obtained containing the following tertiary amines: [ka] Synthesis Example 9 Synthesis of N,N-dimethylaminopropyl oleamide

[0327] In a 100 mL three-necked bottle equipped with a reflux condenser, thermometer, and mechanical stirrer, 3.4 g (0.033 mol) of (CH 3 ) 2 NCH 2 CH 2 CH 2 NH 2 and 13.87 g (0.137 mol) triethylamine were mixed at room temperature. 10 g (0.033 mol) oleic acid chloride was added slowly within 10 min. 5.3 g of an active aqueous solution of 0.2% NaOH was added, followed by 9.2 g deionized water. After phase separation the aqueous phase was removed. In the following three washing cycles 11 g deionized water was added and removed per cycle. The solid phase was dissolved in 10 g 2-propanol. Then the volatiles were removed at 38° C. / 20 mbar.

[0328] A brownish oily liquid was obtained having the following structure: 1 Confirmed by H-NMR): [ka]

[0329] Example 10 Polyfatty Acid-Based Salt Compounds

[0330] The following table shows the carboxylic acids (in the form of -COOH) of the different polyfatty acids described in Synthesis Examples 1 to 7, or alternatively the respective carboxylate Na salts (-COOH - Na + The following outlines salt compounds synthesized by combining stoichiometric amounts of each of the carboxylates (form of carboxylate) with the respective amino / ammonium compounds. To generate the carboxylate forms, a stoichiometric amount of aqueous NaOH was added to 2-propanol containing the polyfatty acid carboxylic acid.

[0331] The following amino / ammonium compounds were used: -Oleylamine -Lysine -N,N-dimethylaminopropyl oleamide according to synthesis example 9 -Polyquaternium 16 -Tetrabutylammonium bromide [Table 12]

[0332] Application Test Combing force measurement To quantify the effect of the compound according to the present invention, the combing force was measured using a small tensile tester MTT175 (Diastrom).

[0333] For this measurement, heavily bleached Caucasian hair (Kerling International) was selected: [Table 13]

[0334] Hair finishing method 1 (one damaged hair) The weight of the hair tress to be finished is determined, and the total amount of active substance calculated (based on the target mg of active substance / g of hair) is added to 2-propanol or 2-propanol and H 2 The amount of 2-propanol used was calculated according to the following formula: m 2-プロパノール (g) = 0.64 x m 仕上げ毛髪 The 2-propanol or 2-propanol / water solution is evenly dispersed onto the hair tresses. The tresses are air dried for 2 hours and further processed as outlined in the general protocol.

[0335] General protocol for preparation and handling of hair tresses Individual hair tresses (2.5 cm) were cut from each storage tress and equilibrated in a humidity chamber at 50% relative humidity (RH) for 12 hours. The dry pull force and the average wet force (tresses were rinsed with 38°C tap water for 30 seconds) were then determined for the untreated tresses (baseline measurements). Three strokes were performed. The force data from the third stroke was used for the calculations.

[0336] The tresses were air dried and equilibrated in a climate chamber for an additional 15 hours. The tresses were then finished with 2-propanol solution as outlined in hair finishing methods 1 and 2, air dried for 2 hours, and equilibrated in a climate chamber for an additional 15 hours. Finally, the dry pull force and wet average force (tresses are rinsed with 38°C tap water for 30 seconds) are determined for the finished tresses (measurements for finished hair). Three strokes were performed. The force data from the third stroke was used for the calculations.

[0337] The ratio between the combing force required before applying the finish (baseline measurement) and the combing force after finishing (measured on finished hair) indicates the effectiveness of the conditioning agent.

[0338] The relative combing force reduction was calculated using the following formula: Force Reduction(%)=(Force ベースライン -force 仕上げ後 )×100 / force ベースライン

[0339] Combing force measurement results Damaged human hair [Table 14]

[0340] The combing force data in the above table for damaged human hair shows that the salt compounds according to the invention are capable of significantly reducing combing force for different keratin materials.

[0341] The data demonstrate that this reduction in combing force can be achieved with a wide variety of polyfatty acid carboxylate structures. Linear structures derived from unsaturated fatty acids (synthetic examples 2 and 3) as well as mixed unsaturated / saturated fatty acid systems (synthetic examples 2a, 2b, 2c) can be used. In addition, branched / dendrimer derivatives (example 4a) also work well. The same is true for branched polyfatty acid carboxylates derived from castor oil (example 7). Non-monofunctional polyfatty acid carboxylates, i.e. bis-carboxylic acid-based polyfatty acid structures (example 6), are also effective on human hair.

[0342] The data also demonstrate that this reduction in combing force can be achieved with a wide variety of amino / ammonium structures. Alkyl-modified primary amines (oleylamine) as well as betaine-like primary amines (lysine) can be used. Additionally, alkyl-modified tertiary amines (Example 9) can be utilized.

[0343] Monoquaternary compounds, such as tetrabutylammonium compounds, and polyquaternized polymers, i.e., polyquaternium 16, in combination with polyfatty acid-based anions, can also provide significant reductions in comb-through force. For monoquaternary compounds, the manner in which the polyfatty acid carboxylates are formed has a large effect.

[0344] Tetrabutylammonium bromide-based examples 10.1 (polyfatty acids in the COOH form; tetrabutylammonium bromide R 4 N + Br - (no true salt formation with -COO - Na + Polyfatty acids in the form of tetrabutylammonium bromide R 4 N + Br - A comparison with the formation of a true salt with -COO according to the present invention reveals the difference. - Na + The use of polyfatty acids in the form of -COOH results in a large reduction in the pulling force when dry as well as the average force when wet. In contrast, the use of polyfatty acids in the form of -COOH, which is not the present invention, results in a significantly lower pulling force when dry as well as the average force when wet. Furthermore, the evaluation of the feel of the hair tresses by the expert panel revealed a significant difference. The treatment of hair with polyfatty acids in the form of -COOH, which is not the present invention, results in a negatively judged dull feel, which is due to the use of -COO - Na + This is in contrast to the smooth feel after treatment with poly fatty acids in the form of

[0345] The formation of a true salt with polyquaternium 16 in Example 10.k also results in a reduction in the dry pull force as well as the wet average force. Furthermore, the expert panel's evaluation of the feel of the hair tresses also revealed significant differences. As was found for the tetrabutylammonium bromide-based Examples 10.l and 10.n, -COO - Na +The treatment of hair according to the invention with polyfatty acids in the form of (10.k) results in a smooth feel after treatment with the polyfatty acids (10.k).

[0346] Based on the considerable flexibility outlined above regarding the polyfatty acid based carboxylate structures, as well as the amino / ammonium structures, suitable salt compounds can be developed for a wide variety of specific applications.

Claims

1. An organic ammonium salt containing an organic ammonium group-containing cation, provided that the organic ammonium group-containing cation does not contain a constituent of formula (III) or (IV): wherein (—Z—C(O)—R ６ ) ｒ —Z—C(O)— (III) or (-C(O)-Z-R ６ ) ｒ -C(O)-Z-(IV), optionally contains one or more groups selected from Z may be the same or different and is selected from -O- or -NR １１ -, where R １１ is hydrogen, or -O-, -NH-, -C(O)-, -C(S)-, 【Chemical 143】 and is independently selected from the group consisting of optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals having up to 100 carbon atoms which may be substituted with one or more of a hydroxyl group and a halide group, R ６ is independently selected from optionally substituted linear, cyclic, or branched hydrocarbon radicals having from 1 to 36 carbon atoms, provided that at least one of the Rs ６ has more than 6 carbon atoms, and r is from 1 to 20, Also, the carboxylic acid anion (COO － ) group-containing anion is selected from the group consisting of the anions of formulas (V), (VII), and (X): Formula (V): R ７ (-X-C(O)-G) ｐ (V) wherein R in formula (V) ７ is selected from optionally substituted hydrocarbon radicals of valence p and is optionally —O—, —NH—, —C(O)—, —C(S)—, 【Chemical 144】 and may contain one or more groups selected from quaternary ammonium groups, and may be optionally substituted by one or more substituents selected from carboxyl (-COOH) groups, carboxylic acid anion (-COO － ), groups and hydroxyl (-OH) groups, p ≥ 1, more preferably 2 to 811, X may be the same or different and is selected from -O- or -NR １０ -, where R １０ is hydrogen, or -O-, -NH-, -C(O)-, -C(S)-, 【Chemical 145】 Optionally containing one or more groups selected from optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals having up to 100 carbon atoms, or of the formula (V) R １０ wherein R ７ may form a bond to form a cyclic structure, G may be the same or different and is optionally -O-, -NH-, -C(O)-, -C(S)-, and 【Chemical Formula 146】 selected from one or more groups and optionally substituted by one or more substituents selected from carboxyl (-COOH) groups, carboxylic acid anion (-COO － ) groups, hydroxyl (-OH) groups, and halide (-halogen) groups, and is selected from optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals having up to 1005 carbon atoms, However, at least one of the radicals G contains at least one constituent of formula (VI) or (VI ＊ ): -R ８ (-X-C(O)-R ８ ) ｍ -X-C(O)-R ９ (VI) -R ８ (-X-C(O)-R ８ ) ｍ -X-C(O)-R ９＊ (VI ＊ ) wherein X is as defined above, m = 0 to 20, preferably 1 to 20, R ８ is independently selected from linear, cyclic, or branched, substituted or unsubstituted divalent hydrocarbon radicals having up to 36 hydrocarbons and optionally substituted, R ９ is optionally —O—, —NH—, —C(O)—, —C(S)—, 【Chemical 147】 comprising one or more groups selected from, and being optionally substituted with one or more substituents selected from carboxyl (-COOH) groups, carboxylic acid anion (-COO － ), hydroxyl (-OH) groups, and halide (-halogen) groups, a linear, cyclic, or branched, substituted or unsubstituted hydrocarbon radical having from 1 to 1000 carbon atoms, independently selected, where the radical R ９ cannot contain an internal carboxy (-COO-) group or a ( -CON(R'), where R' is hydrogen or an organic group) amide group, i.e., R ９ cannot contain a combination of a -C(O)- group and a -O- group or a combination of a -C(O)- group and a -NH- or tertiary amino group, and However, in at least one constituent part of formula (VI) R ９ has at least 2, preferably at least 6 carbon atoms, and in the same constituent part of formula (VI) R ８ at least one has at least 6, preferably at least 8 carbon atoms, However, R ７ and at least one of G has one or more carboxylic acid anion (-COO － ) groups, R ９＊ is optionally —O—, —NH—, —C(O)—, —C(S)—, 【Chemical 148】 comprising one or more groups selected from, and independently selected from hydrocarbon radicals of branched chains or dendrimers having from 1 to 1000 carbon atoms, optionally substituted and substitutable with carboxyl groups, hydroxyl groups, or halide groups, wherein the radical R ９＊ is terminated by two or more groups of the following general structure, -X-C(O)-T wherein X is as defined above, and T is a monovalent linear, cyclic or branched, substituted or unsubstituted hydrocarbon radical of up to 36 hydrocarbons optionally substituted with a carboxyl group, a hydroxyl group or a halide group, However, at least one constituent of formula (VI ＊ )R ９＊ is terminated by one or more groups T having at least 2, preferably at least 6 carbon atoms, and in the same constituent of formula (VI ＊ ) at least one of R ８ has at least 6, preferably at least 8 carbon atoms, However, at least one of R ７ and G in formula (V) contains one or more carboxylate anion (—COO － —) groups, Formula (VII): R ７ (-C(O)-X-Y) ｑ (VII) wherein R ７ and X are as defined above, q = 1 to 55, preferably 1 to 40, more preferably 2 to 4, and Y may be the same or different and is optionally -O-, -NH-, -C(O)-, -C(S)-, and 【Chemical 149】 comprising one or more groups selected from, and being optionally substituted with one or more substituents selected from carboxyl (-COOH) groups, carboxylic acid anion (-COO － ), and hydroxyl groups, and being selected from linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals having up to 1005 carbon atoms However, at least one of the radicals Y contains at least one constituent of formula (VIII) or (VIII ＊ ): -R ８ (-C(O)-X-R ８ ) ｍ -C(O)-X-R ９ (VIII) -R ８ (-C(O)-X-R ８ ) ｍ -C(O)-X-R ９＊ (VIII ＊ ) Here, X, m, R in formula (VIII) ８ , and R ９ are as defined above for formula (VI), and Formula (VIII ＊ ), X, m, R ８ , and R ９＊ are as defined above for formula (VI ＊ ), respectively, and Also, provided that R in formula (VII) ７ and at least one of Y contains one or more carboxylate anion (−COO － ) groups, Formula (X): R ７ (-C(O)-X-R ８ -COO － ) ｑ Here, X, R in formula (X) ７ , R ８ , and q are as defined above for formulas (VII) and (VIII).

2. The organic ammonium group-containing cation is selected from the cations of formula (I): R １ (-F) ｘ (I) wherein x is from 1 to 50, preferably 2 to 50, R １ is selected from x-valent hydrocarbon radicals having from 1 to 1000 carbon atoms, preferably from 2 to 300 carbon atoms, more preferably from 3 to 200 carbon atoms, even more preferably from 3 to 150 carbon atoms, specifically from 3 to 50 carbon atoms, and more specifically from 3 to 20 carbon atoms, optionally substituted, and optionally -O-, -NH-, -C(O)-, -C(S)-, 【Chemical Formula 150】 may contain one or more groups selected from, and R １ is a carboxyl (-COOH) group, a carboxylic acid anion (-COO － ) group, a hydroxyl (-OH) group and a halide (-halogen) group, and may be substituted by one or more groups selected from, and F may be the same or different and is represented by the following general formula (II): 【Chemical Formula 151】 Here, the group F is bonded to a carbon atom of R １ and n is independently from 0 to 1000, R ２ may be the same or different and is optionally —O—, —NH—, —C(O)—, —C(S)—, 【Chemical 152】 comprises one or more groups selected from and is selected from optionally substituted divalent hydrocarbon radicals having up to 1000 carbon atoms, and R ２ is substitutable with one or more groups selected from OH groups and halide groups, and R ３ R ４ R ５ may be the same or different and are hydrogen and optionally -O-, -NH-, -C(O)-, -C(S)-, 【Chemical 153】 selected from optionally substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon radicals having up to 1000 carbon atoms containing one or more groups selected from, and being substitutable with one or more groups selected from an OH group and a halide group, Here, R ３ , R ４ , R ５ is an organic ammonium salt according to claim 1, in which when not hydrogen, each is bonded to the nitrogen atom by a carbon atom.

3. The organic ammonium salt according to claim 1, wherein the organic ammonium group-containing cation is a. mono- and polyquaternary ammonium cations, b. basic amino acid cations, c. mono- and polytertiary amine-based cations, d. mono- and polysecondary amine-based cations, e. mono- and primary amine-based cations selected from the group consisting of.

4. The organic ammonium salt according to claim 1, wherein the organic ammonium group-containing cation has at least 6, preferably at least 10 carbon atoms.

5. The organic ammonium group-containing cation has the formula (I), wherein x is 2 and R １ carries a carboxylic acid anion group and the total charge of the cation is +1. The organic ammonium salt according to claim 1.

6. The carboxylate anion (COO － ) group-containing anion of the organic ammonium salt is selected from the group consisting of the following types of polymeric fatty acid carboxylates, R ７ [(-C(O)-X-R ８ ) ｍ＋１ -C(O)-X-R ９ ｑ or​ R ７ [(X - C(O) - R ８ ) ｍ＋１ - X - C(O) - R ９ ｐ 、​ wherein X, R ７ , R ８ , R ９ , m, p and q are as defined above for formulas (V), (VI), (VII) and (VIII), and wherein R ７ or at least one R ９ , or R ７ and at least one R ９ are one or more carboxylate groups, Preferably X = O, In particular The following types of linear polymeric fatty acid carboxylates, － O—C(O)—R ７ (—X—C(O)—R ８ ) ｍ＋１ —X—C(O)—R ９ 、 preferably － O-C(O)-R ７ -(O-C(O)-R ８ ) ｍ＋１ -O-C(O)-R ９ wherein wherein R ９ is selected from linear, cyclic, or branched, substituted or unsubstituted monovalent hydrocarbon radicals having up to 36 carbon atoms and optionally substituted, Branched linear polymeric fatty acid carboxylates, Or partial esters of polyfunctional carboxylic acids, in particular branched linear polymeric fatty acid carboxylates, dendrimer polymeric fatty acid carboxylates derived from partial esters of succinic acid and maleic acid, which are dicarboxylic acids, with castor oil or lesquerella oil, Or the following types R ７ [(-C(O)-X-R ８ ) ｍ＋１ -C(O)-X-R ９ C(O)O － ｑ or​ (( － OC(O)) ｑ－１ -R ７ -(C(O)-X-R ８ ) ｍ＋１ -C(O)-X-R ９ C(O)O － is where X, R ７ , R ８ , R ９ , m, p and q are as defined above, The following types of carboxylate anions (COO － ) group-containing anions, R ７ [(-C(O)-X-R ８ ) ｍ＋１ -C(O)-X-R ９ C(O)O － ｑ or​ (( － OC(O)) ｑ－１ -R ７ -(C(O)-X-R ８ )) ｍ＋１ -C(O)-X-R ９ C(O)O － Are preferably anions of monovalent to pentavalent, more preferably monovalent to decavalent, even more preferably monovalent to pentavalent, and most preferably pentavalent, tetravalent, trivalent, divalent or monovalent, the organic ammonium salt of Claim 1.

7. The carboxylate anion (COO － ) group-containing anion of the organic ammonium salt contains at least one moiety of general formula (VIa) (-X-C(O)-R ８ ) ｍ -X-C(O)-R ９ (Via) Or contains at least one part of the general formula (VIIIa) (-C(O)-X-R ８ ) ｍ -C(O)-X-R ９ (VIIIa) wherein X and R ８ and m are as defined above, and R ９ optionally contains one or more groups selected from -O-, -NH-, -C(O)-, -C(S)-, and is independently selected from optionally substituted linear, cyclic, or branched, substituted or unsubstituted hydrocarbon radicals having from 1 to 36 carbon atoms which may be substituted with an OH group, a carboxylate group or a halide group, the organic ammonium salt of claim 1.

8. At least one group R ９ is selected from linear alkyl groups and linear alkenyl groups, in particular linear C6-C24 alkyl groups such as hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecylene, nonadecyl, eicosyl, henicosyl, docosyl, tricosyl, and tetracosyl, or linear C6-C24 alkenyl groups such as hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl, henicosenyl, docosenyl, tricosenyl, and tetracosenyl, where this group is most preferably bonded by a terminal carbon atom to an adjacent X group or -C(O)- group, the organic ammonium salt of claim 1.

9. At least one group R ９ is derived from a carboxylic acid or a hydroxycarboxylic acid carrying one or more hydroxyl groups, more preferably from a carboxylic acid or a monohydroxycarboxylic acid, and most preferably from a C7-C25 fatty acid not carrying a hydroxyl group as a substituent, the organic ammonium salt according to claim 1.

10. At least one group R ９ represents an alkyl chain or an alkenyl chain of a carboxylic acid or a hydroxycarboxylic acid obtained by extraction of a carboxylate group, Here preferably the carboxylic acid is selected from acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic 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, γ-linolenic acid, oleic acid, nonadecylic acid, arachidic acid, mead acid, arachidonic acid, heneicosanoic acid, docosanoic acid, tricosylic acid and lignoceric acid, selected from hydroxycarboxylic acids such as lesquerolic acid, ricinoleic acid, 10-hydroxyoctadecanoic acid, 12-hydroxyoctadecanoic acid, 14-hydroxytetradecanoic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or selected from dihydroxycarboxylic acids, in particular 2,2'-dihydroxymethylpropanoic acid, 9,10-dihydroxystearic acid, or polyhydroxycarboxylic acids, in particular gluconic acid, More preferably, at least one R ９ radical is derived from palmitic acid, margaric acid, stearic acid, linoleic acid, α-linolenic acid, γ-linolenic acid, oleic acid, nonadecylic acid, arachidic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, ricinoleic acid, lesquerolic acid or 2,2'-dihydroxymethylpropanoic acid, and Most preferably at least one R ９ radical is derived from oleic acid, stearic acid, lesquerolic acid and ricinoleic acid, the organic ammonium salt of claim 1.

11. In the carboxylic acid anion (COO-) group-containing anions of the general formulas (V), (VII) and (X), X = O, R ８ is independently selected from optionally hydroxyl-substituted hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, docosylene, tricosylene, and tetracosylene, or hexenylene, heptenylene, octenylene, nonenylene, decenylene, undecenylene, dodecenylene, tridecenylene, tetradecenylene, pentadecenylene, hexadecenylene, heptadecenylene, octadecenylene, nonadecenylene, eicosenylene, henicosylene, docosylene, tricosylene, and tetracosylene, where the group is most preferably attached by a terminal carbon atom to an adjacent C(O) group or O group, R ９ is independently selected from optionally hydroxyl-substituted hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, henicosyl, docosyl, tricosyl, and tetracosyl, or hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl, henicosenyl, docosenyl, tricosenyl, and tetracosenyl, where the group is most preferably attached by a terminal carbon atom to an adjacent C(O) group or O group, and m is 0 - 10, preferably 1 - 10, more preferably 1, 2, 3, 4 or 5, the organic ammonium salt of Claim 1.

12. X = O, At least one group R in the anion containing a carboxylic acid anion (COO−) group ８ is selected from hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, hexadecenylene, heptadecenylene, octadecenylene, nonadecenylene, eicosenylene, and At least one R ９ is selected from hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl, And m is 1, 2, 3, 4 or 5, Preferably At least one R ８ is derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid or lesquerolic acid, and At least one R ９ is derived from oleic acid, ricinoleic acid or stearic acid, And m is 1, 2, 3, 4 or 5, the organic ammonium salt of Claim 1.

13. General formula (VI), (VI ＊ ), (VIII) or (VIII ＊ ), each part of which optionally contains a hydroxyl-substituted hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, docosylene, tricosylene, and tetracosylene, or at least one R selected from hexenylene, heptenylene, octenylene, nonenylene, decenylene, undecenylene, dodecenylene, tridecenylene, tetradecenylene, pentadecenylene, hexadecenylene, heptadecenylene, octadecenylene, nonadecenylene, eicosenylene, henicosylene, docosylene, tricosylene, and tetracosylene ８ and contains Preferably, each of the moieties of general formula (VI), (VI ＊ ), (VIII) or (VIII ＊ ) contains at least one R selected from hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, hexadecenylene, heptadecenylene, octadecenylene, nonadecenylene, eicosenylene, optionally hydroxyl-substituted ８ and Also m is 1, 2, 3, 4 or 5, And more preferably, at least one R in each of the moieties of general formula (VI), (VI ＊ ), (VIII) or (VIII ＊ ) is derived from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid or lesquerolic acid, ８ ​ Also m is 1, 2, 3, 4 or 5, the organic ammonium salt of Claim 1.

14. The anion containing a carboxylate anion (COO−) group is a linear carboxylate anion A of the following formula － and contains － O-C(O)-R ７ -(O-C(O)-R ８ ) ｍ＋１ -O-C(O)-R ９ Here, m, R ８ and R ９ are as defined above, R ７ is independently selected from straight-chain, cyclic, or branched, substituted or unsubstituted divalent hydrocarbon radicals having up to 36 carbon atoms, and R ８ +R ９ The total number of carbon atoms in ８ R and R ９ (Σ carbon atoms per anion) is from 19 to 300, preferably from 25 to 300, more preferably from 35 to 300, even more preferably from 50 to 300, specifically from 35 to 200, more specifically from 35 to 150, and even more specifically from 50 to 150, And here, R ７ and R ８ are preferably derived from lactic acid, ricinoleic acid, lesquerolic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, and 14-hydroxytetradecanoic acid, most preferably from ricinoleic acid or lesquerolic acid, R ９ is preferably derived from octadecanoic acid, eicosanoic acid, docosanoic acid, 2-ethylhexanoic acid, 2,2-dimethylpropionic acid, neodecanoic acid, oleic acid, and The organic ammonium salt according to claim 1, wherein m is preferably from 1 to 10, more preferably from 1 to 6, even more preferably from 1 to 6, and specifically 1, 2, 3, 4, 5, 6, 7.

15. The general formula sequence is － O-C(O)-R ７ -(O-C(O)-R ８ ) ｍ＋１ -O-C(O)-R ９ where where m, R ７ , R ８ and R ９ are as defined above, and in the above formula, R ７ , R ８ and R ９ are selected as follows, the organic ammonium salt of claim 14. 【Table 15】

16. The carboxylate anion (COO−) group-containing anion is a branched linear polymeric fatty acid carboxylate, particularly a partial ester of a polyfunctional carboxylic acid, particularly a partial ester of succinic acid and maleic acid, which are dicarboxylic acids, and castor oil or lesquerella oil, or glycerin esterified with a hydroxy fatty acid containing at least one moiety of the following formula: Glycerin - O - C(O) - R ８ -(O - C(O) - R ８ ) ｍ -O - C(O) - R ９ wherein R ８ is as defined above, preferably derived from lactic acid, ricinoleic acid, lesquerolic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, 14-hydroxytetradecanoic acid, most preferably derived from ricinoleic acid or lesquerolic acid, R ９ is as defined above and is preferably derived from stearic acid, eicosanoic acid, docosanoic acid, 2-ethylhexanoic acid, 2,2-dimethylpropionic acid, neodecanoic acid, oleic acid, succinic acid and maleic acid, succinic anhydride and maleic anhydride, and in the moiety of the formula shown above, m = 0 to 20, preferably 1 to 20, more preferably 1 to 10, even more preferably 1 to 6, particularly 0, 1, 2, 3, 4, 5, 6, 7, and R ８ + R ９ The total number of carbon atoms in (R ８ and R ９ i.e., the Σ carbon atoms) is from 19 to 300, preferably from 25 to 300, more preferably from 35 to 300, even more preferably from 50 to 300, specifically from 35 to 200, more specifically from 35 to 150, and even more specifically from 50 to 150. The organic ammonium salt according to claim 1.

17. There is at least one sequence of the following general formula, glycerin-O-C(O)-R ８ -(O-C(O)-R ８ ) ｍ -O-C(O)-R ９ Here, m, R ８ and R ９ are as defined above and are selected from the following, 【Table 16】 The organic ammonium salt according to claim 16, wherein preferably two sequences are selected according to the above table.

18. The carboxylic acid anion (COO−) group-containing anion is the branched-chain or dendrimer-type polymeric fatty acid carboxylic acid anion A of formula (V) － which contains Formula (VI) or (VI ＊ ) wherein R ７ 、 X, R ８ 、 R ９ 、 R ９＊ and m are as described above, wherein R ７ groups carry at least one anionic carboxylate group and are preferably derived from bishydroxymonocarboxylic acids such as glyceric acid and 2,2-bis-(hydroxymethyl)propionic acid, R ８ is as defined above, preferably derived from lactic acid, ricinoleic acid, lesquerolic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, 14-hydroxytetradecanoic acid, and most preferably from ricinoleic acid or lesquerolic acid, R ９ is as defined above, preferably derived from octadecanoic acid, eicosanoic acid, docosanoic acid, 2-ethylhexanoic acid, 2,2-dimethylpropionic acid, neodecanoic acid, and stearic acid, oleic acid, and R ９＊ In [R], T is preferably derived from octadecanoic acid, eicosanoic acid, docosanoic acid, 2-ethylhexanoic acid, 2,2-dimethylpropionic acid, neodecanoic acid, stearic acid, and oleic acid, m = 1 to 20, preferably 1 to 10, more preferably 1 to 6, even more preferably 1 to 6, particularly 1, 2, 3, 4, 5, 6, 7, R ８ + R ９ The total number of carbon atoms in (R ８ and R ９ the Σ carbon atoms) is from 19 to 300, preferably from 25 to 300, more preferably from 35 to 300, even more preferably from 50 to 300, specifically from 35 to 200, more specifically from 35 to 150, and even more specifically from 50 to 150, the organic ammonium salt of claim 1.

19. General formula R ７ (-X-C(O)-R ８ ) ｍ -X-C(O)-R ９ In at least one sequence of, X and m as defined above are selected from the following, 【Table 17】 The organic ammonium salt according to claim 18, wherein preferably all the groups of such sequences are selected according to the above table.

20. The anion containing a carboxylate anion (COO−) group is a carboxylate anion A of the following types － including R ７ [(-C(O)-X-R ８ ) ｍ＋１ -C(O)-X-R ９ C(O)O － ｑ or​ (( － OC(O)) ｑ－１ -R ７ -(C(O)-X-R ８ )) ｍ＋１ -C(O)-X-R ９ C(O)O － Here, X = O, R ７ , R ８ , R ９ , m and q are as defined above, and Preferably q = 2 to 4, particularly 2, 3, 4, R ８ is as defined above, preferably derived from lactic acid, ricinoleic acid, resceroleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, 14-hydroxytetradecanoic acid, most preferably from ricinoleic acid or resceroleic acid, R ７ is as defined above, preferably derived from maleic acid, succinic acid, trimellitic acid, pyromellitic acid, and m = 0 to 20, preferably 1 to 20, more preferably 1 to 10, even more preferably 1 to 6, even more preferably 1 to 6, particularly 1, 2, 3, 4, 5, 6, 7, and R ８ +R ９ The total number of carbon atoms in (the Σ carbon atoms of R ８ and R ９ per anion) is from 19 to 300, preferably from 25 to 300, more preferably from 35 to 300, even more preferably from 50 to 300, specifically from 35 to 200, more specifically from 35 to 150, and even more specifically from 50 to 150, for the organic ammonium salt of Claim 1.

21. General formula R ７ [(-C(O)-X-R ８ ) ｍ＋１ -C(O)-X-R ９ C(O)O － ｑ and​ ( － OC(O)) ｑ－１ -R ７ -(C(O)-X-R ８ ) ｍ＋１ -C(O)-X-R ９ C(O)O － At least one sequence of the polyacid ester in is selected from the following, 【Table 18】 The organic ammonium salt according to claim 20, wherein preferably all such sequences of the anion are selected according to the above table.

22. The organic ammonium group-containing cation is selected from cations according to the general formula defined above R １ (-F) ｘ (I) where x is 1 to 10, preferably 1 to 5, more preferably 1, 2, 3, 4, 5, most preferably 1 and 2, F may be the same or different and is represented by the general formula (II): 【Chemical 154】 Here, R １ , R ２ , R ３ , R ４ , R ５ and n are as defined above, and preferably n = 0 - 100, even more preferably 0 - 50, even more preferably 0 - 20, most preferably 0, 1, 2, 3, 4 or 5, for the organic ammonium salt of claim 1.

23. The organic ammonium group-containing cation is selected from cations conforming to the general formula defined above R １ (-F) ｘ (I) wherein x = 2, and the cation is represented by the general formula (V): 【Chemical 155】 wherein R １ , R ２ , R ３ , R ４ , R ５ and n are as defined above, and preferably n = 0 - 1000, preferably 0 - 100, more preferably 0 - 50, even more preferably 0 - 20, and most preferably 0, 1, 2, 3, 4 or 5, for the organic ammonium salt of claim 1. **Claim 24** The organic ammonium group-containing cation is selected from cations conforming to the general formula defined above R １ (-F) ｘ (I) wherein x is from 1 to 10, preferably from 1 to 5, more preferably 1, 2, 3, 4, or 5, and most preferably 1 or 2, R １ has from 1 to 1000 carbon atoms, preferably from 2 to 300 carbon atoms, more preferably from 3 to 200 carbon atoms, even more preferably from 3 to 150 carbon atoms, specifically from 3 to 50 carbon atoms, and more specifically from 3 to 20 carbon atoms, and optionally -O-, -NH-, -C(O)-, -C(S)-, 【Chemical 156】 and may contain one or more groups selected from Preferably R １ is a C3-C18 glycerin-based polyether radical or a C1-C8 straight-chain alkylene radical, and F has the general formula (XVII) corresponding to formula (II) where n is equal to 0: 【Chemical 157】 And the group F is bonded to a carbon atom of R １ and wherein R ３ 、R ４ 、R ５ are hydrogen and have up to 300 carbon atoms, preferably from 1 to 200 carbon atoms, more preferably from 1 to 150 carbon atoms, even more preferably from 1 to 50 carbon atoms, specifically from 1 to 20 carbon atoms, and more specifically from 1 to 10 carbon atoms, and optionally -O-, -NH-, -C(O)-, -C(S)-, 【Chemical 158】 and may contain one or more groups selected from Preferably R ３ to R ５ is a C1-C8 linear alkyl group such as methyl, ethyl, propyl or butyl, the organic ammonium salt of claim 1. **Claim 25** The carboxylic acid anion (COO － ) group-containing anion is preferably a monovalent to pentavalent anion, more preferably a monovalent to decavalent anion, even more preferably a monovalent to pentavalent anion, most preferably a pentavalent, tetravalent, trivalent, divalent or monovalent anion, and is the organic ammonium salt of claim 1. **Claim 26** Carboxylate anion (COO － ) groups containing anions include at least one moiety of general formula (XI) or (XII): -X-C(O)-R ｘ -(X-C(O)-R ｘ ) ｍ -X-C(O)-R ９ (XI) or -X-C(O)-R ｘ -(X-C(O)-R ｘ ) ｍ -X-C(O)-R ９ (XII) In the formula X is O or NR １１ , m = 1 to 20, preferably 1 to 10, more preferably 1 to 6, even more preferably 2 to 6, and particularly 1, 2, 3, 4, 5, 6, R ｘ +R ９ The total number of carbon atoms of (R per anion, ｘ R ９ the Σ carbon atoms of R) is from 19 to 300, preferably from 25 to 300, more preferably from 35 to 300, even more preferably from 50 to 300, specifically from 35 to 200, more specifically from 35 to 150, and even more specifically from 50 to 150. R １１ is as defined above and is preferably hydrogen, n-, iso-, or tert-C １ -C ２２ -alkyl, more preferably hydrogen, R ｘ is optionally OH, -O-C(O)-R ９ , -O-C(O)-R ８ -(O-C(O)-R ８ ) ０－１９ -O-C(O)-R ９ substituted, and is a straight-chain, cyclic, or branched, substituted or unsubstituted hydrocarbon radical having from 1 to 36 carbon atoms, preferably from 1 to 24 carbon atoms, more preferably from 1 to 18 carbon atoms, even more preferably from 8 to 18 carbon atoms, excluding the carbon atoms of the R ８ and R ９ group-containing substituents, and is preferably derived from a monohydroxycarboxylic acid, particularly glycolic acid, lactic acid, 2-hydroxybutyric acid, 3-hydroxybutyric acid, 4-hydroxybutyric acid, 14-hydroxytetradecanoic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, lesquerolic acid, ricinoleic acid, or a dihydroxycarboxylic acid, particularly 2,2'-dihydroxy-2-methylpropanoic acid, 9,10-dihydroxystearic acid, or a polyhydroxycarboxylic acid, particularly gluconic acid R ８ is as defined above, R ９ is optionally selected from linear, cyclic, or branched, substituted or unsubstituted hydrocarbon radicals having from 1 to 36 carbon atoms, preferably from 1 to 24 carbon atoms, more preferably from 1 to 18 carbon atoms, even more preferably from 8 to 18 carbon atoms, preferably derived from acetic acid, octanoic acid, nonanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, eicosanoic acid, docosanoic acid, 2-ethylhexanoic acid, 2,2-dimethylpropionic acid, 2,2-dimethylheptanoic acid, 2,2-dimethyloctanoic acid, neodecanoic acid, undecyl-10-enoic acid, oleic acid, linoleic acid, linolenic acid, erucic acid, and R ８ is independently selected from hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, henicosylene, docosylene, tricosylene, and tetracosylene, or hexenylene, heptenylene, octenylene, nonenylene, decenylene, undecenylene, dodecenylene, tridecenylene, tetradecenylene, pentadecenylene, hexadecenylene, heptadecenylene, octadecenylene, nonadecenylene, eicosenylene, henicosenylene, docosenylene, tricosylene, and tetracosylene, optionally substituted with hydroxyl; more preferably independently selected from hexadecylene, heptadecylene, octadecylene, nonadecylene, eicosylene, hexadecenylene, heptadecenylene, octadecenylene, nonadecenylene, eicosenylene, optionally substituted with hydroxyl; most preferably each R ８ is preferably independently selected from ricinoleic acid, 10-hydroxystearic acid, 12-hydroxystearic acid, or lesquerolic acid, the organic ammonium salt of claim 1. **Claim 27** The organic ammonium group-containing cation is the general formula defined above R １ (-F) ｘ (I) selected from cations according to, wherein R １ is selected from the group consisting of linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbyl groups having a valence of 1 to 18, preferably 2 to 18, more preferably 2 to 6, even more preferably 2, 3 and 4, optionally substituted with -O-, -C(O)-, OH or amide: - which is derived from primary, secondary and tertiary amines and quaternary ammonium compounds having at least one, preferably more than one, more preferably 3, and even more preferably more than 3 carbon atoms, particularly derived from - primary amines such as C1 to C24 primary amines, namely methylamine, ethylamine, propylamine, isopropylamine, butylamine, hexylamine, cyclohexylamine, octylamine, 2-ethylhexylamine, decylamine, undecenylamine, dodecylamine, tetradecylamine, hexadecylamine, octadecylamine, oleylamine, OH-functionalized primary amines, namely ethanolamine, glucamine, aminoglycerin, polyether-based primary amines, namely mono-, di-, and tri-functional primary amines of polyethylene oxide and polypropylene oxide-based, - Derived from the condensation product of epoxy compounds, especially glycidyl ethers and alcohols, especially 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, glycerin, diglycerin, triglycerin and higher linear or branched oligoglycerins, trimethylolpropane, castor oil (ricinoleic acid triglyceride), pentaerythritol, sorbitol, such as polyethylene glycols like diethylene glycol, triethylene glycol, tetraethylene glycol, and pentaethylene glycol, or derived from dipropylene glycol (e.g., derived from 2,2'-oxydi-1-propanol, 1,1'-oxydi-2-propanol, and 2-(2-hydroxypropoxy)-1-propanol), polypropylene glycols like tripropylene glycol, tetrapropylene glycol, pentapropylene glycol, derived from mixed (ethylene oxide) and (butylene oxide) copolymers, derived from mixed (propylene oxide)- and (butylene oxide) copolymers, and derived from mixed (ethylene oxide)- and (propylene oxide)- and (butylene oxide) copolymers, poly(alkylene oxide) such as (ethylene oxide)-, (propylene oxide)- and / or (butylene oxide)-based polyethers, or preferably glycidyl esters and acids, especially neodecanoic acid, and ammonia - Derived from basic amino acids such as lysine, arginine, histidine or their ester or amide derivatives - Derived from secondary amines, especially C1 to C24 secondary amines such as N-methylamines like dimethylamine, N-methyloctylamine, N-methyldodecylamine, N-methyloctadecylamine, N-ethylamines like diethylamine, N-butylamines like dibutylamine, cyclic amines like piperazine, morpholine Polyether-based secondary amines such as polyethylene oxide and polypropylene oxide-based difunctional secondary amines or polyethyleneimine, - Derived from the condensation product of epoxy compounds, in particular glycidyl ethers and alcohols, especially methanol, ethanol, 2-propanol, 1-butanol, t-butanol, undec-10-en-1-ol, oleyl alcohol, stearyl alcohol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,2-hexanediol, 1,6-hexanediol, glycerin, diglycerin, triglycerin and higher linear or branched oligoglycerins, trimethylolpropane, castor oil (ricinoleic acid triglyceride), pentaerythritol, sorbitol, such as polyethylene glycols like diethylene glycol, triethylene glycol, tetraethylene glycol, and pentaethylene glycol, or derived from dipropylene glycol (e.g., derived from 2,2'-oxydi-1-propanol, 1,1'-oxydi-2-propanol, and 2-(2-hydroxypropoxy)-1-propanol), polypropylene glycols like tripropylene glycol, tetrapropylene glycol, pentapropylene glycol, derived from mixed (ethylene oxide) and (butylene oxide)-based copolymers, derived from mixed (propylene oxide)- and (butylene oxide)-based copolymers, and derived from mixed (ethylene oxide)- and (propylene oxide)- and (butylene oxide)-based copolymers, poly(alkylene oxide) such as (ethylene oxide)-, (propylene oxide)- and / or (butylene oxide)-based polyethers, or preferably glycidyl esters and acids, especially neodecanoic acid, and primary amines, namely methylamine, ethylamine, butylamine, cyclohexylamine, octylamine, 2-ethylhexylamine, undecenylamine, dodecylamine, hexadecylamine, stearylamine, oleylamine, ethylenediamine, 1,2-propylenediamine, 1,3-propylenediamine, 1,4-butanediamine, 1,6-hexanediamine, 1,10-decanediamine, 1,12-dodecanediamine, basic amino acids, such as N-methyllysine, - Derived from tertiary amines, in particular 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''-pentamethyldiethylenetriamine, N,N,N',N'',N''-pentamethyldipropylenetriamine, 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, N-methylmorpholine, N-ethylmorpholine, N,N'-dimethylpiperazine, N,N-dimethylbenzylamine, N,N-dimethylcyclohexylamine - Derived from the condensation product of epoxy compounds, in particular glycidyl ethers and alcohols, especially 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, glycerin, diglycerin, triglycerin and higher linear or branched oligoglycerins, trimethylolpropane, castor oil (ricinoleic acid triglyceride), pentaerythritol, sorbitol, such as polyethylene glycols like diethylene glycol, triethylene glycol, tetraethylene glycol, and pentaethylene glycol, or derived from dipropylene glycol (e.g., derived from 2,2'-oxydi-1-propanol, 1,1'-oxydi-2-propanol, and 2-(2-hydroxypropoxy)-1-propanol), polypropylene glycols like tripropylene glycol, tetrapropylene glycol, pentapropylene glycol, derived from mixed (ethylene oxide) and (butylene oxide)-based copolymers, derived from mixed (propylene oxide)- and (butylene oxide)-based copolymers, and derived from mixed (ethylene oxide)- and (propylene oxide)- and (butylene oxide)-based copolymers, poly(alkylene oxide) such as (ethylene oxide)-, (propylene oxide)- and / or (butylene oxide)-based polyethers, or preferably glycidyl esters and acids, especially neodecanoic acid, and primary or secondary amino-functional amines, especially methylamine, ethylamine, butylamine, cyclohexylamine, octylamine, 2-ethylhexylamine, undecenylamine, dodecylamine, hexadecylamine, stearylamine, oleylamine, ethylenediamine, 1,2-propylenediamine, 1,3-propylenediamine, 1,4-butanediamine, 1,6-hexanediamine, 1,10-decanediamine, 1,12-dodecanediamine, N,N-dimethylethylenediamine, N,N-dimethylpropylenediamine, N,N,N',N'-tetramethyl-diethylenetriamine, N,N,N',N'-tetramethyl-dipropylenetriamine, N-methylpiperazine - Derived from condensation products of carboxylic acids, in particular C6-C24 fatty acids, i.e. hexanoic acid, 2-ethylhexanoic acid, octanoic acid, decanoic acid, undecenoic acid, dodecanoic acid, tetradecanoic acid, hexadecenoic acid, octadecanoic acid, oleic acid, ricinoleic acid, lesquerolic acid, 12-hydroxystearic acid, di- and higher carboxylic acids, i.e. succinic acid, sebacic acid, trimellitic acid, with primary-tertiary amines, i.e. N,N-dimethylpropylenediamine, N,N-dimethylethylenediamine, N-dodecyl-N-bis-(propylamine), and secondary-tertiary amines, i.e. N,N,N',N'-tetramethyldiethylenetriamine, N,N,N',N'-tetramethyldipropylenetriamine, N-methylpiperazine, N-ethylpiperazine - Derived from a monoquaternary ammonium compound, such as a C1-C30 tetraalkyl-substituted ammonium compound, preferably Cl － , Br － , CH ３ -O-SO ３ － or OH － Having a counterion, i.e., a compound having the same alkyl substituent, i.e., (C ２ H ５ ) ４ N ＋ Cl － , (C ２ H ５ ) ４ N ＋ OH － , (C ４ H ９ ) ４ N ＋ Br － , (C ４ H ９ ) ４ N ＋ OH － , preferably a mono-long-chain alkyltri-short-chain alkyl quaternary ammonium salt or a di-long-chain alkyldi-short-chain alkyl quaternary ammonium salt, a compound having different alkyl substituents, where one or two alkyl substituents are an aliphatic or aromatic group of about 8 to about 30 carbon atoms, an alkoxy group having up to about 30 carbon atoms, a polyoxyalkylene group, an alkylamide group, a hydroxyalkyl group, an aryl group or an alkylaryl group, and the other alkyl groups are independently an aliphatic or aromatic group of about 1 to about 8 carbon atoms, an alkoxy group having up to about 8 carbon atoms, a polyoxyalkylene group, an alkylamide group, a hydroxyalkyl group, an aryl group or an arylalkyl group, the aliphatic group can include other groups such as ether linkages and amino groups in addition to carbon and hydrogen atoms, the longer-chain aliphatic group, e.g., an aliphatic group of about 8 or more carbon atoms can be saturated or unsaturated, preferably one alkyl group is selected from alkyl groups of about 8 to about 30 carbon atoms, more preferably about 14 to about 26 carbon atoms, even more preferably about 14 to 22 carbon atoms, and the other alkyl groups are independently CH ３ , C ２ H ５ , C ２ H ４ OH, CH ２ , C ６ H ５ selected from the group consisting of and mixtures thereof, and the counterion is Cl － , Br － , CH ３ OSO ３ － selected from and mixtures thereof C1-C30 tetraalkyl-substituted ammonium compounds contain an ester moiety and preferably Cl － , Br － , CH ３ -O-SO ３ － and have counterions of, preferably, cationic saturated or unsaturated fatty acid-based mono- and diester quats, with the alkyl chains derived from fatty acids having from 10 to 22, preferably from 10 to 18 carbon atoms Ethoxylated C10-C18 saturated and unsaturated monoesterquats, for example cocoil pentaethoxymethylammonium methosulfate C10-C18, preferably C16-C18 saturated and unsaturated diesterquats derived from triethanolamine C10-C18, preferably C16-C18 saturated and unsaturated triesterquats derived from triethanolamine, C10-C18, preferably C16-C18 saturated and unsaturated esterquats derived from N-methyl-diethanolamine, C10-C18, preferably C16-C18 saturated and unsaturated esterquats derived from N,N-dimethyl-3-aminopropane-1,2-diol, C16-C18 saturated and unsaturated esterquats derived from N-dimethyl-diisopropanolamine, - Symmetric or asymmetric diquaternary ammonium compounds crosslinked with a head group or a tail group, i.e., gemini-type quats, especially diquaternary compounds containing at least one, preferably at least two C10-C30, more preferably C10-C22, even more preferably C10-C18 alkyl groups, especially derived from diquaternary compounds with a crosslinked head group, For example, diquaternary compounds containing an alkyl crosslink, preferably a C2-C30 alkyl crosslink, For example, diquaternary compounds crosslinked with ethers and esters, preferably C4-C30 diquaternary compounds containing ether and ester crosslinks, For example, diquaternary ammonium compounds crosslinked with hydroxyalkyls, preferably glycerin, more preferably containing a C3-C30 glycerin crosslink, For example, diquaternary ammonium compounds containing a fatty acid or aliphatic alcohol ester moiety, preferably C6-C30, preferably C10-C30, more preferably C10-C22, even more preferably C16-C18 fatty acid or aliphatic alcohol ester moieties, - Especially derived from triquaternary ammonium compounds Preferably triquaternary compounds containing at least one, preferably at least two C10-C30, more preferably three C10-C22, even more preferably C10-C18 alkyl groups, - Especially polyquaternary compounds, preferably polyquaternium compounds registered in INCI, such as polyquaternium 1 to polyquaternium 113, and polyquaternium 1 to polyquaternium 47, especially polyquaternium 16 is preferred - Derived from polyquaternary compounds based especially on polysaccharides, preferably cellulose, guar gum, chitin and chitosan, more preferably quaternized cellulose and crosslinked quaternized cellulose (hydrogel), quaternized guar gum, quaternized chitin, and quaternized chitosan, the organic ammonium salt of claim 1.

28. The cation containing an organic ammonium group has the general formula defined above R １ (-F) ｘ (I) selected from cations according to, wherein R １ is - Monovalent to 18-valent, preferably divalent to 18-valent, more preferably divalent to 6-valent, even more preferably divalent, trivalent and tetravalent, optionally OH, amino or amide-substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon groups, which are derived from alkyl halides having more than one, preferably more than two carbon atoms, such as alkyl chlorides, bromides, iodides, such as 1,3-dichloropropane, 1,3-dichlorobutane, 1,4-dichlorobutane, dichloro-monohydroxypropane isomers, 1,2,3-trichloropropane, 1,2-dichlorohexanediol, 1,2-dichlorohexane, or the corresponding bromides and iodides - A monovalent to 18-valent, preferably divalent to 18-valent, more preferably divalent to 6-valent, even more preferably divalent, trivalent and tetravalent, optionally OH, amino or amide substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon group selected, which in total (esters) has more than two, preferably more than three carbon atoms, a halogenated carboxylic acid, preferably an ester of a chloro carboxylic acid, for example chloroacetic acid, 3-chloropropionic acid, 4-chlorobutyric acid or the respective bromo carboxylic acids and alcohols, in particular 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, glycerin, diglycerin, triglycerin and higher linear or branched oligoglycerins, trimethylolpropane, castor oil (ricinoleic acid triglyceride), pentaerythritol, sorbitol, for example polyethylene glycols such as diethylene glycol, triethylene glycol, tetraethylene glycol, and pentaethylene glycol, or 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, polypropylene glycols, derived from mixed (ethylene oxide) and (butylene oxide) copolymers, derived from mixed (propylene oxide)-and (butylene oxide) copolymers, and derived from mixed (ethylene oxide)-and (propylene oxide)-and (butylene oxide) copolymers, esters with poly(alkylene oxides) such as (ethylene oxide)-, (propylene oxide)-and / or (butylene oxide)-based polyethers, - Monovalent to 18-valent, preferably divalent to 18-valent, more preferably divalent to 6-valent, even more preferably divalent, trivalent and tetravalent, optionally OH-substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon groups, which have more than 3, preferably more than 4 carbon atoms in total, and are preferably derived from ethers or esters of epoxy compounds which are derived from epoxy compounds having an ability to open the ring with an alcohol, the alcohol being in particular 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, glycerin, diglycerin, triglycerin and higher linear or branched oligoglycerins, trimethylolpropane, castor oil (ricinoleic acid triglyceride), pentaerythritol, sorbitol, such as polyethylene glycols such as diethylene glycol, triethylene glycol, tetraethylene glycol, and pentaethylene glycol, or dipropylene glycol (derived from, for example, 2,2'-oxydi-1-propanol, 1,1'-oxydi-2-propanol, and 2-(2-hydroxypropoxy)-1-propanol), polypropylene glycols such as tripropylene glycol, tetrapropylene glycol, pentapropylene glycol, derived from mixed (ethylene oxide) and (butylene oxide) copolymers, derived from mixed (propylene oxide)- and (butylene oxide) copolymers, and derived from mixed (ethylene oxide)- and (propylene oxide)- and (butylene oxide) copolymers, poly(alkylene oxide) such as (ethylene oxide)-, (propylene oxide)- and / or (butylene oxide)-based polyethers, or preferably glycidyl esters with acids, in particular neodecanoic acid, - Monovalent to 18-valent, preferably divalent to 18-valent, more preferably divalent to 6-valent, even more preferably divalent, trivalent and tetravalent, optionally OH-substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon groups selected therefrom, which in total have more than 7, preferably more than 8 carbon atoms, preferably a glycidyl ether epoxy compound, and a carboxylic acid having a valence of two to six, especially maleic acid, succinic acid, adipic acid, sebacic acid, itaconic acid, tartaric acid, trimellitic acid, dimer fatty acid ether, Particularly preferably a carboxylic acid having a valence of two to six, such as maleic acid, succinic acid, adipic acid, sebacic acid, itaconic acid, tartaric acid, trimellitic acid, dimer fatty acid, and a divalent to hexavalent alcohol or alkylene oxide as described above, such as ethylene oxide, propylene oxide, butylene oxide, a carboxyl (-C(O)OH)-functionalized polyester formed by condensation, and a compound containing at least one glycidoxy group, such as glycidol, diglycidyl ether, glycerin diglycidyl ether, glycerin triglycidyl ether and oligomer glycerin glycidyl ether, butanediol diglycidyl ether ether, especially succinic acid, maleic acid and tartaric acid, dimer fatty acid and glycerin diglycidyl ether, polyester condensation product, particularly preferably an oligomeric hydroxycarboxylic acid, especially oligomerized lactic acid, 12-hydroxystearic acid, resquerolic acid, ricinoleic acid-derived -Valent from monovalent to 18-valent, preferably divalent to 18-valent, more preferably divalent to 6-valent, even more preferably divalent, trivalent and tetravalent, optionally OH-substituted linear, cyclic or branched, saturated, unsaturated or aromatic hydrocarbon groups, which are selected from, in total more than 5, preferably more than 6 carbon atoms, a halogenated carboxylic acid, preferably an ester of a chloro carboxylic acid, such as chloroacetic acid, 3-chloropropionic acid, 4-chlorobutyric acid or their respective bromo carboxylic acids, and an OH-functionalized polyester, particularly preferably a carboxylic acid of divalent to hexavalent, such as maleic acid, succinic acid, adipic acid, sebacic acid, itaconic acid, tartaric acid, trimellitic acid, dimer fatty acid, and a divalent to hexavalent alcohol or alkylene oxide as described above, such as ethylene oxide, propylene oxide, butylene oxide, and a compound containing at least one glycidoxy group, such as glycidol, diglycidyl ether, glycerin diglycidyl ether, glycerin triglycidyl ether and oligomer glycerin glycidyl ether, butanediol diglycidyl ether, formed by condensation, particularly a condensation product of succinic acid, maleic acid and tartaric acid or dimer fatty acid and glycerin diglycidyl ether, the organic ammonium salt of claim 1.

29. The organic ammonium group-containing cation has the general formula defined above R １ (-F) ｘ (I) selected from cations according to, wherein R １ is selected from poly(alkylene oxide) groups, preferably from poly(alkylene oxide) groups of the general formula (XIII): - [CH ２ CH ２ O] ｑ１ - [CH ２ CH(CH ３ )O] ｒ１ - [CH ２ CH(C ２ H ５ )O] ｓ１ -{[CH ２ CH ２ - ｑ２ - [CH ２ CH(CH ３ )] ｒ２ - [CH ２ CH(C ２ H ５ )] ｓ２} - (XIII) where q1 = from 0 to 49, preferably from 0 to 10, more preferably from 1 to 10, even more preferably from 1 to 5, r1 = from 0 to 32, preferably from 0 to 10, more preferably from 1 to 10, even more preferably from 1 to 5, s1 = from 0 to 24, preferably from 0 to 10, more preferably from 1 to 10, even more preferably from 1 to 5, q2 = 0 or 1, r2 = 0 or 1, s2 = 0 or 1, and Σ(q2 + r2 + s2) = 1, provided that the total number of carbon atoms in this poly(alkylene oxide) moiety is from 2 to 100, preferably from 2 to 50, more preferably from 2 to 30, even more preferably from 2 to 20, particularly from 2 to 15, or R １ is selected from divalent hydrocarbon groups derived from oligoglycerols of general formula (XIV): - [CH ２ CH(R １２ )CH ２ O] ｔ１ - [CH ２ CH(R １２ )CH ２ )] ｔ２ - (XIV) where t1 = from 0 to 32, preferably from 0 to 10, more preferably from 1 to 10, even more preferably from 1 to 5, particularly 1 and 2, t2 = 1, R １２ = OH or -O-C(O)-R ６ -N ＋ (R ３ 、R ４ 、R ５ ) Here, R ３ , R ４ , R ５ and R ６ are as defined above, However, the total number of carbon atoms is from 2 to 100, preferably from 2 to 50, more preferably from 2 to 30, even more preferably from 2 to 20, particularly from 2 to 15, or R １ is A divalent hydrocarbon group of general formula (XV) containing at least one ester group: - [CH ２ CH ２ O] ｑ１ - R １３ - [CH ２ CH ２ O] ｑ１ - [CH ２ CH ２ ｑ２ - (XV)​ wherein q1 is the same or different and as defined above, q2 = 1, and a divalent hydrocarbon group of general formula (XVI) containing at least one ester group: - [CH ２ CH(R １２ )CH ２ O] ｔ１ - R １３ - [CH ２ CH(R １２ )CH ２ O] ｔ１ - [CH ２ CH(R １２ )CH ２ )] ｔ２ - (XVI) selected from where t1, t2 and R １２ are as defined above, and R １３ is selected from -C(O)C(O)O-, -C(O)(CH ２ ) １－８ C(O)O-, for example succinic acid, adipic acid, sebacic acid, or -C(O)(C ６ H ４ )C(O)O-, that is, phthalic acid and terephthalic acid, -C(O)CH=CHC(O)O-, -C(O)C(=CH ２ )-CH ２ C(O)O-, -C(O)CH(OH)CH(OH)C(O)O-, and is derived from However, R １３ the total number of carbon atoms in is from 2 to 100, preferably from 2 to 50, more preferably from 2 to 30, even more preferably from 2 to 20, particularly from 2 to 15, and preferably q2 = 0, and one or two of q1, r1 and s1 are 0, and more preferably q2 = 0, r1 and s1 are 0, or q2 = 0, q1 and s1 are 0, or R １ is a group containing one or more, for example from 1 to 5, groups -O-, these groups -O- preferably being ether groups, but being able to form ester groups together with a carbonyl group, and preferably the group R １ is an organic ammonium salt according to claim 1, which is substituted by one or more hydroxyl groups.

30. The carboxylic acid anion (COO － ) group-containing anion of the organic ammonium salt of formula (V) or (VII), in at least one of the moieties of formula (VI), (VI ＊ ) or (VIII), (VIII ＊ ), where two or more different R ８ groups are present. The organic ammonium salt according to claim 1.

31. The carboxylic acid anion (COO － ) group-containing anion of the organic ammonium salt of formula (V) or (VII), in at least one of the moieties of formula (VI), (VI ＊ ) or (VIII), (VIII ＊ ), the groups R ８ and R ９ or R ８ and R ９＊ are not based on the same carboxylic acid structure, the organic ammonium salt according to claim 1.

32. In formula (V), p is 2 - 6, R ７ is selected from straight-chain, branched-chain or cyclic alkylene groups, straight-chain, branched-chain or cyclic alkenylene groups, straight-chain, branched-chain or cyclic alkynylene groups, straight-chain, branched-chain or cyclic alkarylene groups, straight-chain, branched-chain or cyclic aralkylene groups, and straight-chain, branched-chain or cyclic arylene groups, such as phenylene, benzylene or tolylene groups, having a valence of from di to hexa, in particular such groups having from 1 to 1000 carbon atoms, more particularly from 1 to 150 carbon atoms, and at least one group G comprises one or more moieties of general formula (VI ＊ ), -R ８ (-X-C(O)-R ８ ) ｍ -X-C(O)-R ９＊ (VI ＊ ) where R ８ , R ９＊ and m are as defined above, or In formula (VII), q is 2 - 6, R ７ is selected from straight-chain, branched-chain or cyclic alkylene groups, straight-chain, branched-chain or cyclic alkenylene groups, straight-chain, branched-chain or cyclic alkynylene groups, straight-chain, branched-chain or cyclic alkarylene groups, straight-chain, branched-chain or cyclic aralkylene groups, and straight-chain, branched-chain or cyclic arylene groups, such as phenylene, benzylene or tolylene groups, having a valence of di to hexa, in particular such groups having from 1 to 1000 carbon atoms, more particularly from 1 to 150 carbon atoms, and at least one group Y comprises one or more moieties of general formula (VIII ＊ ), -R ８ (-C(O)-X-R ８ ) ｍ -C(O)-X-R ９＊ (VIII ＊ ) wherein R ８ , R ９＊ and m are as defined above, the organic ammonium salt of claim 1.

33. In the carboxylic acid anion (COO － ), X = O, and p is 2, R ７ is selected from divalent linear, branched and cyclic alkylene groups, in particular linear C1-C22 alkyl groups such as methylene, ethylene, n-propylene, n-butylene, n-pentylene, n-hexylene, n-heptylene or n-octylene groups, and also from branched C1-C22 alkylene groups such as isopropylene, isobutylene, tert-butylene, isobutylene, tert-pentylene, neopentylene, and 2-ethylhexylene groups, preferably selected from ethylene, n-propylene, n-butylene, n-pentylene and n-hexylene, and at least one group G contains one or more moieties of the general formula (VI ＊ ), -R ８ (-X-C(O)-R ８ ) ｍ -X-C(O)-R ９＊ (VI ＊ ) where R ８ , R ９＊ and m are as defined above, or In the carboxylic acid anion (COO － ) group-containing anion of formula (VII), X = O, and q is 2, R ７ is selected from divalent linear, branched and cyclic alkylene groups, in particular linear C1-C22 alkyl groups such as methylene, ethylene, n-propylene, n-butylene, n-pentylene, n-hexylene, n-heptylene or n-octylene groups, and also from branched C1-C22 alkylene groups such as isopropylene, isobutylene, tert-butylene, isobutylene, tert-pentylene, neopentylene, and 2-ethylhexylene groups, preferably selected from ethylene, n-propylene, n-butylene, n-pentylene and n-hexylene, and at least one group Y contains one or more moieties of the general formula (VIII ＊ ), -R ８ (-C(O)-X-R ８ ) ｍ -C(O)-X-R ９＊ (VIII ＊ ) wherein R ８ , R ９＊ and m are as defined above, the organic ammonium salt of claim 1.

34. In the carboxylic acid anion (COO － ), one or more groups R ９＊ are each terminated by three or more groups -O-C(O)-T, preferably each by four or more groups -O-C(O)-T, most preferably each by four to twelve groups -O-C(O)-T, where T is as defined above, the organic ammonium salt of claim 32.

35. In the carboxylic acid anion (COO － ), group containing anion), one or more groups R ９＊ each contain at least two branched structures of the following general formula, -C(O)-B(-O-) ｂ wherein B is a linear or branched hydrocarbon group having 2 to 20 carbon atoms, b is 2 or greater, and the b group (-O-) linked to the B group on one side is linked to a carbon atom, which carbon atom may be the carbon atom of the CH ２ group on the other side or the carbon atom of the carbonyl group, the organic ammonium salt according to claim 32.

36. In the carboxylic acid anion (COO － ), one or more groups R ９＊ in the anion containing the group defined above by the general formula -B(-O-) ｂ or -C(O)-B(-O-) ｂ of one or more branched structures are independently derived from glyceric acid, 2,2-dihydroxymethylpropionic acid, gluconic acid, maltobionic acid, lactobionic acid, the organic ammonium salt of claim 32.

37. The carboxylic acid anion (COO － ) group-containing anion of formula (V) or (VII), one or more groups R ９＊ are each terminated by two or more groups of the following structure, -R ８ (-X-C(O)-R ８ ) ｔ -X-C(O)-T, where R ８ and T are as defined above, and X = O, t is independently 0 - 12, preferably t is independently 0 - 6, most preferably t is independently 0, 1, 2 or 3, the organic ammonium salt of claim 1.

38. The carboxylic acid anion (COO － group-containing anion of formula (V) or (VII), one or more groups R ９＊ are terminated by two or more groups, preferably from 4 to 12 groups, of the following structure, -R ８ (-X-C(O)-R ８ ) ｔ -X-C(O)-T wherein R ８ is independently derived from C8-C24 monocarboxylic acid-monohydroxycarboxylic acid, particularly from ricinoleic acid, 12-hydroxystearic acid, lesquerolic acid, 11-hydroxy-undecanoic acid, X is O, and T is independently derived from fatty acids of C2 to C24, preferably C8 to C24, particularly from lauric acid, myristic acid, palmitic acid, oleic acid, stearic acid, behenic acid, arachidic acid, and t is 0 - 6, preferably 0, 1, 2 or 3, the organic ammonium salt of claim 1.

39. One or more of the following general formula (VI ＊ ), in the carboxylate anion (COO － )-group-containing anion of formula (V) containing a moiety of -R ８ (-X-C(O)-R ８ ) ｍ -X-C(O)-R ９＊ (VI ＊ ) wherein R ８ , R ９＊ and m are as defined above, or a carboxylic acid anion (COO ＊ ) group-containing anion of formula (VII) containing one or more moieties of the following general formula (VIII － ), -R ８ (-C(O)-X-R ８ ) ｍ -C(O)-X-R ９＊ (VIII ＊ ) where R ８ , R ９＊ and m are as defined above, One or more groups R ９＊ are independently selected from one of the following branched or dendrimer fatty acid structures, -R １４ -O-C(O)-R １５ -(O-C(O)-R １６ ) ｍ１ -(O-C(O)-R １７ ) ｍ２ -O-C(O)-T or -R １４ -NR １０ -C(O)-R １５ -(O-C(O)-R １６ ) ｍ１ -(O-C(O)-R １７ ) ｍ２ -O-C(O)-T, wherein R １０ is as defined above, R １４ is optionally —O—, —NH—, —C(O)—, —C(S)—, 【Chemical 159】 may contain one or more groups selected from —OH or halide groups, a divalent hydrocarbon radical having 2 to 50 carbon atoms, particularly 2 to 20 carbon atoms, more particularly 2 to 10 carbon atoms, optionally substituted and substitutable by an —OH or halide group, wherein the radical R １４ shall not contain a combination of a —C(O)— group and an —O— group or a combination of a —C(O)— group and an —NH— or tertiary amino group that form an internal carboxylate group or an internal amide group, and preferably a C1-C24 n-alkylene group and a C2-C24 n-alkenylene group, particularly —CH ２ —, —CH ２ CH ２ —, —CH ２ CH ２ CH ２ —, representing R １５ is independently selected from a linear, cyclic, or branched, optionally substituted divalent hydrocarbon radical having up to 36 carbon atoms, or a C2-C24 monocarboxylic acid having from 2 to 6 hydroxy groups, such as 2,2'-dihydroxymethylpropanoic acid, m1 is from 0 to 12, preferably from 0 to 10, more preferably from 0 to 6, even more preferably from 1 to 6, particularly 0, 1, 2, 3, 4, 5, 6, m2 is from 0 to 12, preferably from 0 to 10, more preferably from 0 to 6, even more preferably from 1 to 6, particularly 0, 1, 2, 3, 4, 5, 6, and m1 + m2 is t, where t is from 0 to 12, preferably from 0 to 10, more preferably from 0 to 6, even more preferably from 1 to 6, particularly 0, 1, 2, 3, 4, 5, 6, T is as defined above, R １６ and R １７ is selected from the R １５ groups defined above, and preferably 【Table 19】 Here, R １５ + the total number of carbon atoms of T (R １５ , the Σ carbon atoms of T) is from 19 to 300, preferably from 25 to 300, more preferably from 35 to 300, even more preferably from 50 to 300, particularly from 35 to 200, more specifically from 35 to 150, and even more specifically from 50 to 150, and However, for R, R and R which are derived from di- or polyhydroxylated carboxylic acids, the organic ammonium salt according to claim 1, in which at least one, preferably one to two, more preferably two, and even more preferably all OH groups are esterified. １５ R １６ and R １７ are as defined in claim 1, provided that at least one, preferably one to two, more preferably two, and even more preferably all OH groups are esterified.

40. The carboxylate anion (COO−) group-containing anion of formula (V) is represented by the following schematic ester structure: － O(O)C-(C1-C12 radical)-C(O)-O-(mono- or oligo-C8-C24 hydroxy fatty acid)-C(O)-O-(C2-C10 hydrocarbon)-O-C(O)-(mono- or oligo-C8-C24 hydroxy fatty acid)-O-C(O)-(C1-C12 radical)-C(O)O － , wherein the terminal C1 - C12 radical is selected from linear, branched, saturated, unsaturated or aromatic C1 - C12 radicals, preferably C2 - C12, C2 - C10, C2 - C4 radicals, more preferably C2 and C4 radicals, the organic ammonium salt of claim 1.

41. The carboxylic acid anion (COO － ) group-containing anion of formula (V) or (VII) contains at least one moiety of the following general formula: -([-O-C(O)-R ８ (-O-C(O)-R ８ )l-O-C(O)-L-C(O)-O-(R ８ -C(O)-O)l-R ８ -C(O)O])- wherein R ８ is as defined above, l is an integer independently selected from 0 - 20, more preferably from 1 - 12, even more preferably from 2 - 10, and L is a divalent hydrocarbon radical which may have from 1 to 30 carbon atoms and optionally also -O-, -S-, -NH-, -C(O)-, -C(S)-, 【Chemical 160】 and may contain one or more groups selected from quaternary ammonium groups, preferably L is a divalent alkylene or alkenylene radical having from 1 to 30 carbon atoms, more preferably L is selected from methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, ethenylene, propenylene, butenylene, pentenylene, hexenylene, heptenylene, octenylene, nonenylene, and most preferably L is selected from methylene, ethylene, ethenylene or butenylene, the organic ammonium salt of claim 1.

42. The carboxylic acid anion (COO － ) group-containing anion of formula (V) or (VII) contains at least one moiety of the following general formula -([-O-C(O)-R ８ (-O-C(O)-R ８ )l-O-C(O)-L-C(O)-O-(R ８ -C(O)-O)l-R ８ -C(O)O])- where L and l are as defined above in the previous embodiment, and R ８ is independently derived from C8-C24 monocarboxylic acid-monohydroxycarboxylic acid, in particular ricinoleic acid, 12-hydroxystearic acid, lesquerolic acid, 11-hydroxy-undecanoic acid, most preferably R ８ is derived from ricinoleic acid, the organic ammonium salt of claim 41.

43. The carboxylic acid anion (COO － ) group-containing anion of formula (V) or (VII) contains at least one moiety of the following structure: (aliphatic alcohol)-O-C(O)-(mono or oligo C8-C24 hydroxy fatty acid)-O-C(O)-(C2-C12 hydrocarbon)-C(O)-O-(mono or oligo C8-C24 hydroxy fatty acid)-C(O)-O-(aliphatic alcohol), the organic ammonium salt of claim 1.

44. The carboxylic acid anion (COO － ) group-containing anion of formula (V) or (VII) contains at least one moiety of the following structure -([-O-C(O)-R ８ (-O-C(O)-R ８ ) ｌ -O-C(O)-L-C(O)-O-(R ８ -C(O)-O) ｌ -R ８ -C(O)O])-R ９ where L, l, R ８ and R ９ are as defined above, the organic ammonium salt of claim 41.

45. The R, G or Y of the carboxylic acid anion (COO － ), group-containing anion of formula (V) or (VII) has at least one group of at least one of the following formulas ７ including at least one part of the following formula R １＊ [(-O-C(O)-R ８ ) ｍ -O-C(O)-] ２ wherein R １＊ is a divalent C1-C100 radical, preferably a C1-C12 alkylene, most preferably methylene, ethylene, 1,3-propylene, 1,4-butylene, 1,6-hexylene, 1,2-propylene, 1,3-butylene radical, and m is independently selected from 1 to 12, and R ８ The organic ammonium salt according to claim 1, which is as defined above.

46. in at least one moiety of the following general formula R １＊ [(-O-C(O)-R ８ ) ｍ -O-C(O)-] ２ R １＊ is selected from methylene, ethylene, 1,3-propylene, 1,4-butylene, 1,6-hexylene, 1,2-propylene, 1,3-butylene, and R ８ is derived from C8-C24 monocarboxylic acid-monohydroxycarboxylic acid, particularly ricinoleic acid, 12-hydroxystearic acid, lesquerolic acid, 11-hydroxy-undecanoic acid, and m is independently selected from 1 to 6, the organic ammonium salt of claim 45.

47. A process for producing an organic ammonium salt according to any one of claims 1 to 46, comprising: The reaction of an organic amine corresponding to an organic ammonium group-containing cation with a carboxylic acid (—COOH) corresponding to an anion containing a carboxylic acid anion (COO － ), or Reaction of an inorganic anion-containing salt of an organic ammonium group-containing cation with a metal salt of a carboxylic acid (-COOH) corresponding to an anion containing a (COO － group selected from the group consisting of formula (V), (VII) and (X); or A process comprising the reaction of a hydroxy salt of an organic ammonium group-containing cation with a carboxylic acid corresponding to an anion containing a carboxylic acid anion (COO － ), selected from the group consisting of formula (V), (VII) and (X).

48. The production of the organic ammonium salt according to any one of claims 1 to 46 includes an anion exchange reaction step (ii), and an alkali metal salt or alkaline earth metal salt of a carboxylic acid (—COOH) corresponding to a carboxylate anion (COO － ),) group-containing anion is applied, a process according to claim 47.

49. (ii) a reaction of an inorganic anion-containing salt of an organic ammonium group-containing cation with a metal salt of a carboxylic acid (-COOH) corresponding to an anion containing a carboxylate anion (COO － ) group, wherein a Na carboxylate or K carboxylate containing an anion containing a carboxylate anion selected from the group consisting of formula (V), (VII) and (X) is contacted with an inorganic anion-containing salt of an organic ammonium group-containing cation selected from primary, secondary, tertiary, quaternary amine salts containing chloride, bromide or methosulfate anions, The process for producing an organic ammonium salt according to claim 47. － ) group-containing anion, wherein the Na carboxylate or K carboxylate containing the anion containing the carboxylate anion selected from the group consisting of formula (V), (VII) and (X) is selected from primary, secondary, tertiary and quaternary amine salts containing chloride, bromide or methosulfate anions. The process for producing an organic ammonium salt according to claim 47, which is contacted with an inorganic anion-containing salt of an organic ammonium group-containing cation.

50. The anion exchange reaction (ii) that yields the target salt compound according to any one of claims 1 to 46 is carried out in a separate reaction step prior to any contact with other components of the final cosmetic formulation, the process according to claim 47.

51. A carboxylic acid anion (COO － ), preferably a sodium salt and a potassium salt, of a carboxylic acid (—COOH) corresponding to an anion containing a group) is added to a partial cosmetic formulation or a finished cosmetic formulation containing a primary, secondary, tertiary or quaternary amine salt containing an inorganic counter ion. The process according to claim 47.

52. The production of the organic ammonium salt according to any one of claims 1 to 46 includes an anion exchange reaction step (iii), and in which a carboxylic acid corresponding to a carboxylate anion (COO-) group-containing anion selected from the group consisting of formulas (V), (VII) and (X) is contacted with a primary, secondary, tertiary amine and a quaternary ammonium ion having an OH- counter ion, the anion exchange reaction step (iii) is carried out in a separate reaction step prior to any contact with other components of the final cosmetic formulation, the process of claim 47.

53. The production of the organic ammonium salt according to any one of claims 1 to 46 includes an anion exchange reaction step (iii), and in which the carboxylic acid corresponding to the carboxylate anion (COO−) group selected from the group consisting of formulas (V), (VII) and (X) is added to and contacted with a partial cosmetic formulation or a finished cosmetic formulation containing a primary, secondary, tertiary or quaternary amine salt having an OH− counter ion. The process of claim 47.

54. Use of the organic ammonium salt according to any one of claims 1 to 46 in a skin care cosmetic formulation, a hair care conditioner and shampoo cosmetic formulation, particularly in a conditioner and shampoo, as an abrasive for treating and coating a hard surface, for example in a formulation for drying an automobile and other hard surfaces after washing the automobile, for finishing a fiber product and the fibers of a fiber product, as a separate softener after the fiber product has been washed with a nonionic or anionic / nonionic detergent formulation, as a softener in a formulation based on a nonionic or anionic / nonionic surfactant for washing a fiber product, and as a means for preventing or removing wrinkles in a fiber product.

55. Use of the organic ammonium salt according to any one of claims 1 to 46 in a cosmetic composition for treating fibers, preferably amino acid-based fibers, more preferably human hair, particularly for retaining hair color, improving hair shine, improving hair color, protecting hair color, conditioning hair, smoothing or softening hair, improving hair manageability, particularly improving combability of hair.

56. A hair treatment composition comprising the organic ammonium salt according to any one of claims 1 to 46, selected from the group consisting of a hair shampoo composition, a hair conditioner composition, a hair color or hair dye composition, a hair combability improvement composition, a hair rinse-off and leave-on composition.

57. In skin care cosmetics formulations, hair care conditioners and shampoo cosmetics formulations, particularly in conditioners and shampoos, in abrasives for treating and coating hard surfaces, for example in formulations for drying automobiles and other hard surfaces after automobile washing, for finishing textile products and the fibers of textile products, as a separate softener after textile products have been washed with a nonionic or anionic / nonionic detergent formulation, as a softener in a formulation based on a nonionic or anionic / nonionic surfactant for washing textile products, and as a means for preventing or removing wrinkles in textile products, use of the product of the process according to claim 47.

58. In a cosmetic composition for treating fibers, preferably amino acid-based fibers, more preferably human hair, particularly for hair color retention, improvement of hair shine, improvement of hair color, protection of hair color, hair conditioning, smoothing or softening of hair, improvement of hair manageability, particularly improvement of hair combability, use of the product of the process according to claim 47.

59. A composition for treating hair, comprising the product of the process according to claim 47, selected from the group consisting of a hair shampoo composition, a hair conditioner composition, a hair color or hair dye composition, a composition for improving hair combability, a hair rinse-off and leave-on composition.

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