Use of a mixture of cationic surfactants for dispersing quaternary ammonium ester components in water

Abstract

The present invention provides the use of a mixture of cationic surfactants for dispersing a quaternary ammonium ester component comprising one or more compounds of formula (IV) in water, wherein the mixture of cationic surfactants is obtainable by a process comprising the steps of: (a) esterification of a hydroxyl-containing compound or mixture of hydroxyl-containing compounds with a mixture of compounds containing one or more carboxyl groups, and (b) forming a cation from the reaction product of step I. The present invention also provides compositions and uses thereof. Advantageously, the dispersions of the present invention are highly stable. The quaternary ammonium ester component comprises one or more compounds of formula (IV), (IV)

Description

Technical Field

[0001] This invention relates to the use of mixtures of cationic surfactants for dispersing quaternary ammonium ester compounds in water, which can be used to prepare fabric softener compositions. Background Technology

[0002] Quaternary ammonium ester compounds, commonly known as "ester-based quaternary ammonium salts" (EQ), have been widely used as active ingredients in fabric softeners due to their high softening properties (e.g., for softening textile fibers and fabrics as well as keratin fibers such as hair), their biodegradability, relatively low aquatic toxicity, and good cosmetic compatibility.

[0003] Fabric softener formulations containing ester-based quaternary ammonium salts require specific manufacturing processes (including stirring and temperature conditions) to ensure stability and prevent phase separation in aqueous dispersions. Furthermore, the softener active formulation, when combined with fragrance, should exhibit a clear, viscous liquid that can be directly and readily dispersed in water (including tap water) at temperatures ranging from 5°C to 40°C, wherein such formulations are homogeneous and stable during storage.

[0004] Another requirement for fabric softener formulations is to reduce their environmental footprint from manufacturing to use as a softener ingredient, thereby achieving more sustainable products. This can lead to various beneficial effects, such as water reduction, plastic reduction, energy conservation, and / or the eco-acceptability of the product and its use. The possibility of dispersing fabric softeners in water at low temperatures (i.e., 5°C to 40°C) can reduce the need for resources for water treatment (for fabric softener manufacturers) and allows end consumers to prepare fabric softeners directly from concentrated softeners at home, dispersing the softener directly in tap water (which is readily available in the home).

[0005] WO2016096614A1 describes a fabric treatment agent comprising a specific ester-based quaternary ammonium salt. A fabric softener formulation with high storage stability is provided only in the presence of a cationic thickener and a nonionic emulsifier.

[0006] EP1136471A1 describes cationic surfactants obtained from alkanolamines, dicarboxylic acids, and fatty alcohols. This patent describes the efficacy of such cationic surfactants in softening and conditioning natural and synthetic fibers.

[0007] In view of the above, the present invention aims to solve the problem of providing a homogeneous and stable ester-based quaternary ammonium salt dispersion that is insensitive to water hardness and can be readily prepared at room temperature. Summary of the Invention

[0008] The inventors have discovered that a stable aqueous dispersion of the ester-based quaternary ammonium salt of interest can be obtained by pre-mixing an ester-based quaternary ammonium salt with a mixture of cationic surfactants of specific properties.

[0009] Therefore, the present invention provides the use of a mixture of cationic surfactants for dispersing at least a quaternary ammonium ester component in water, the mixture of cationic surfactants being obtained by a method comprising the following steps:

[0010] Step I: esterification reactions a) and b), and

[0011] Step II: A cation is formed from the reaction product of Step I, wherein:

[0012] a) is a hydroxyl-containing compound or a mixture of hydroxyl-containing compounds, comprising a.1 and optionally a.2, wherein:

[0013] - a.1 is an alkanolamine or a mixture of alkanolamines of general formula (I):

[0014]

[0015] R1 is selected from hydrogen, C1-C6 alkyl groups, and residues.

[0016]

[0017] R2 is a C1-C6 alkylene group, R3 is hydrogen or methyl, and n is 0 or an integer from 1 to 20; and

[0018] - a.2 is a polyol, which is optionally alkoxylated, and is characterized by a molecular weight (MW) in the range of 60 g / mol to 190 g / mol;

[0019] b) is a mixture of compounds containing one or more carboxyl groups, comprising b.1 and b.2, wherein:

[0020] - b.1 is a monocarboxylic acid or a mixture of monocarboxylic acids of formula (II):

[0021] R6-COOH (II)

[0022] Wherein R6 is a straight-chain or branched C6-C23 alkyl or alkenyl group; or an alkyl ester or glycerol ester thereof, preferably a straight-chain or branched C6-C23 alkyl or alkenyl ester; and

[0023] - b.2 is a dicarboxylic acid or a mixture of dicarboxylic acids of general formula (III), or one or more of its reactive derivatives:

[0024] HOOC-L-COOH (III)

[0025] Wherein L is a saturated or unsaturated straight-chain or branched group having 1 to 10 carbon atoms, or a cyclic group having 3 to 10 carbon atoms, each carbon atom optionally substituted with a C1-C6 saturated or unsaturated group; and preferably (CH(R11)). m Alternatively, it can be represented by (C6-C10 aryl) optionally substituted with one or more R11, wherein each R11 is independently hydrogen, OH or a C1-C6 saturated or unsaturated group, and m is an integer from 0 to 10, wherein for m ≥ 2, the chain (CH)m optionally contains one or more double bonds and / or cyclic groups (one or more).

[0026] Where a.1), a.2), b.1), and b.2) are introduced into the reaction system of step I in the following molar ratios:

[0027] - The molar ratio (b.1 / b.2) of monocarboxylic acid (one or more) / diacarboxylic acid (one or more) is from 0.3 to 5.0; preferably

[0028] - The equivalence ratio (COOH / OH) of organic carboxylic acid groups to organic hydroxyl groups in the system is 0.4 to 0.8;

[0029] - The molar ratio between compounds (one or more) defined in a.2 and compounds (one or more) defined in a.1 is 0 to 0.5;

[0030] The quaternary ammonium ester component includes one or more compounds of formula (IV):

[0031]

[0032] in

[0033] X1 indicates a hydroxyalkyl group containing 1 to 4 carbon atoms or an alkyl group containing 1 to 4 carbon atoms;

[0034] R7 is a straight-chain or branched C6-C23 alkyl or alkenyl group, preferably C10-C22 alkyl or alkenyl group, more preferably C14-C20 alkyl or alkenyl group, and even more preferably C16-C18 alkyl or alkenyl group.

[0035] R8 and R9 each independently represent -H, -OH, or -O-Tq-C(O)-R7;

[0036] T represents the -(OCH2CH2)a-(OCHR4CH2)b– group, wherein R4 represents an alkyl group containing 1 to 4 carbon atoms, a represents an average number in the range of 0 to 20, b represents an average number in the range of 0 to 6, and the sum of a+b represents the average degree of alkoxylation corresponding to the number from 0 to 26; preferably 0 to 6, most preferably 0;

[0037] q represents the average number in the range of 0 to 26;

[0038] m, r, and p each independently represent the average number in the range of 1 to 4, and A represents an anion, preferably a halide, phosphate, or alkyl sulfate.

[0039] The present invention also provides a method for dispersing a quaternary ammonium ester component in water, the quaternary ammonium ester component comprising one or more compounds of formula (IV) as defined above, the method comprising the steps of: (i) mixing one or more compounds of formula (IV) with a cationic mixture as defined above, (ii) adding water, and (iii) stirring.

[0040] The present invention also provides a composition comprising a cationic mixture as defined above and a quaternary ammonium ester component. The composition may optionally contain a fragrance. The composition may be a softening composition; the softener composition may be a diluted softener composition comprising such a mixture or a concentrated softener composition. The composition may be used to soften fabrics or fibers, for example, by dispersing the composition with water (including tap water). Detailed Implementation

[0041] Terms not specifically defined herein shall be given the meanings as understood by those skilled in the art based on this disclosure and the context. However, unless otherwise specified, the following terms used in this specification shall have the indicated meanings and shall follow the following conventions.

[0042] In this specification and the appended terms, the word "comprise" and its variations such as "comprises" and "comprising" should be interpreted as inclusive. That is, where the context permits, these words are intended to convey that other elements or integers not specifically listed may be included. The word "comprise" also includes the term "consists of". For the purposes of this invention, any scope given includes both the lower and upper limits of that scope.

[0043] For the purposes of this invention, any range given includes both the lower limit endpoint and the upper limit endpoint of that range.

[0044] Unless otherwise stated, all percentages are by weight.

[0045] The inventors have surprisingly discovered that when a quaternary ammonium ester component is mixed with a mixture of specific cationic surfactants, a homogeneous and stable aqueous dispersion of the quaternary ammonium ester component can be obtained. Furthermore, this dispersion is insensitive to water hardness and can be readily prepared at room temperature by simple mixing.

[0046] Mixture of cationic surfactants

[0047] A mixture of cationic surfactants can be obtained by a method comprising the following steps: Step I: esterification reaction of a) and b), and Step II: formation of a cation from the reaction product of Step I, wherein:

[0048] a) is a hydroxyl-containing compound or a mixture of hydroxyl-containing compounds, comprising a.1 and optionally a.2, wherein:

[0049] a.1) is an alkanolamine or a mixture of alkanolamines of general formula (I):

[0050]

[0051] R1 is selected from hydrogen, C1-C6 alkyl groups, and residues.

[0052]

[0053] R2 is a C1-C6 alkylene group, R3 is hydrogen or methyl, and n is 0 or an integer from 1 to 20; and

[0054] a.2) is a polyol, which is optionally alkoxylated and is characterized by a molecular weight (MW) in the range of 60 g / mol to 190 g / mol;

[0055] b) is a mixture of compounds containing one or more carboxyl groups, comprising b.1 and b.2, wherein:

[0056] b.1) is a monocarboxylic acid or a mixture of monocarboxylic acids of formula (II):

[0057] R6-COOH (II)

[0058] Wherein R6 is a straight-chain or branched C6-C23 alkyl or alkenyl group; or an alkyl ester or glycerol ester thereof, preferably a straight-chain or branched C6-C23 alkyl or alkenyl ester; and

[0059] b.2) is a dicarboxylic acid or a mixture of dicarboxylic acids of general formula (III), or one or more of its reactive derivatives:

[0060] HOOC-L-COOH (III)

[0061] Wherein L is a saturated or unsaturated straight-chain or branched group having 1 to 10 carbon atoms, or a cyclic group having 3 to 10 carbon atoms, each carbon atom optionally substituted with a C1-C6 saturated or unsaturated group; and preferably (CH(R11)). mThe expression is represented by (C6-C10 aryl) substituted with one or more R11, wherein each R11 is independently hydrogen, OH or a C1-C6 saturated or unsaturated group, and m is an integer from 0 to 10, wherein for m ≥ 2, the chain (CH)m optionally contains one or more double bonds and / or cyclic groups (one or more).

[0062] Where a.1), a.2), b.1), and b.2) are introduced into the reaction system of step I in the following molar ratios:

[0063] - The molar ratio (b.1 / b.2) of monocarboxylic acid (one or more) / dicarboxylic acid (one or more) is 0.3 to 5.0;

[0064] - The equivalence ratio (COOH / OH) of organic carboxylic acid groups to organic hydroxyl groups in the system is 0.4 to 0.8; and

[0065] - The molar ratio between one or more compounds in definition a.2 and one or more compounds under definition a.1 is 0 to 0.5.

[0066] In one embodiment of the invention, the molar ratio (b1 / b2) of the monocarboxylic acid / diacarboxylic acid is 0.3 to 5.0, preferably 0.6 to 4.0, and more preferably 1.5 to 4.0.

[0067] In another embodiment of the invention, the molar ratio (b1 / b2) of the monocarboxylic acid / diacarboxylic acid is 0.3 to 5.0, 0.6 to 4.0, 2.0 to 4.0, 1.0 to 4.0, or 0.6 to 2.5.

[0068] In another embodiment of the present invention, the equivalence ratio (COOH / OH) of the organic carboxylic acid groups to the organic hydroxyl groups present in the system is 0.4 to 0.8, preferably 0.5 to 0.7.

[0069] In one embodiment of the invention, the molar ratio between the compound (one or more) defined in a.2 and the compound (one or more) defined in a.1 is 0 or 0.1 to 0.5, preferably 0 (i.e., in the absence of any polyols).

[0070] Without being bound by theory, these specific ratios, individually or in combination, contribute to further improving the softening effect and / or stability of formulations formed by using mixtures of cationic surfactants according to the invention.

[0071] In one embodiment of the invention, the molar ratio of monocarboxylic acid to dicarboxylic acid (b1 / b2) is 1.5 to 4.0, the equivalence ratio between organic carboxylic acid groups and organic hydroxyl groups (COOH / OH) is 0.5 to 0.7, and the molar ratio between the compound (one or more) defined in a.2 and the compound defined in a.1 is 0.

[0072] In one embodiment of the invention, the alkanolide (one or more) of formula (I) is selected from triethanolamine, N-methyldiethanolamine, N-methyldiisopropanolamine and triisopropanolamine, each of which is optionally alkoxylated with ethylene oxide or propylene oxide and mixtures thereof.

[0073] In one embodiment of the present invention, in the dicarboxylic acid (one or more) of formula (III), each L is selected from ethane-1,2-diyl, 1-hydroxyethane-1,2-diyl, cis-ethylene-1,2-diyl, trans-ethylene-1,2-diyl, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, cyclohexane-1,4-diyl, octane-1,8-diyl, and 1,4-phenylene; preferably butane-1,4-diyl, hexane-1,6-diyl, or octane-1,8-diyl.

[0074] In another embodiment of the invention, the dicarboxylic acid of formula (III) is selected from succinic acid, malic acid, glutaric acid, adipic acid, sebacic acid, pimelic acid, octanoic acid, maleic acid and terephthalic acid, acids obtained by thermal oligomerization of unsaturated fatty acids and mixtures thereof.

[0075] In one embodiment of the present invention, the reactive derivatives (one or more) of the dicarboxylic acid (III) of general formula (III) are selected from one or more halides, acid anhydrides (preferably acid anhydrides mixed with acetic acid or cyclic acid anhydrides).

[0076] The monocarboxylic acid (one or more) of formula (II) is a synthetic fatty acid and / or obtained from fats or oils of natural origin and optionally hydrogenated; or derived from oils of plant origin which are optionally hydrogenated.

[0077] In one embodiment of the invention, the monocarboxylic acid (one or more) of formula (II) is selected from monocarboxylic acids obtained from tallow, palm, olive, coconut, sunflower, soybean, rapeseed, grape pomace and grape, each of which may be hydrogenated, partially hydrogenated or non-hydrogenated.

[0078] In one embodiment of the present invention, the carboxylic acid monocarboxylic acid (one or more) of formula (II) is selected from one or more of the following: hexanoic acid, octanoic acid, 2-ethylhexanoic acid, decanoic acid, lauric acid, isotoleic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, transoleic acid, phellandrene, linoleic acid, linolenic acid, tung oil acid, arachidic acid, gadolinic acid, benzyl acid and erucic acid and mixtures thereof, which are obtained, for example, by pressure cracking of natural fats and oils, by reduction of aldehydes in Roelen's carbonyl synthesis, or by dimerization of unsaturated fatty acids, stearic acid, isostearic acid, palmitic acid, myristic acid, lauric acid, decanoic acid, octanoic acid, 2-ethylhexanoic acid, 2-octyldodecanoic acid, decanoic acid, oleic acid, linoleic acid, linolenic acid, partially hydrogenated coconut fatty acid, palm fatty acid, partially hydrogenated distilled palm fatty acid, hydrogenated distilled palm fatty acid, palm kernel fatty acid, tallow fatty acid, distilled tallow fatty acid and rapeseed fatty acid.

[0079] In another embodiment of the invention, the iodine value of one or more carboxylic acid monocarboxylic acids of formula (II) is 0 to 150, 20 to 100, 30 to 100, 65 to 85, or 20 to 80.

[0080] In another embodiment of the invention, the compounds corresponding to a.1 and / or a.2 may be derived from natural or synthetic sources.

[0081] In one embodiment of the invention, polyol a.2 is selected from one or more of trimethylolpropane (TMP), glycerol and neopentyl glycol (NPG), each of which may optionally be alkoxylated, preferably ethoxylated; wherein polyol a.2 is more preferably trimethylolpropane (TMP), or is not present.

[0082] Step I is an esterification step that reacts a) with b). In an exemplary embodiment, a monobasic acid b.1 and a dibasic acid b.2 are combined with an alkanolamine a.1 and optionally a polyol b.2. The resulting mixture is heated. Preferably, the mixture is heated under atmospheric pressure and refluxed, for example at 140°C to 200°C, preferably 160°C to 180°C, for 1 to 5 hours, preferably 2 to 4 hours. Preferably, Step I is carried out until no more water is distilled from the reaction mixture.

[0083] The reaction product obtained in step I undergoes cation formation in step II. Preferably, an organic solvent is added before step II. The organic solvent is inactive in the chemical reaction, but its addition is to promote the reaction occurring in step II. Step II may correspond to the formation of an addition salt of the alkanolamine ester obtained in step I with an inorganic or organic acid, preferably wherein the inorganic or organic acid is one or more selected from hydrochloric acid, sulfuric acid, phosphoric acid, citric acid, and lactic acid. Alternatively, step II may correspond to the quaternization reaction of the reaction mixture of step I with one or more alkylating agents, preferably wherein the alkylating agent is one or more selected from methyl chloride, methyl bromide, dimethyl sulfate, diethyl sulfate, and dimethyl carbonate. Step II may be carried out at room temperature or elevated temperatures, for example, 40°C to 100°C, preferably 50°C to 90°C; preferably for 1 to 5 hours, more preferably 2 to 4 hours, or until the amine value is verified to be almost completely absent by acid / base determination.

[0084] In one embodiment of the invention, the mixture further comprises an organic solvent, preferably an alcohol, more preferably ethanol, n-propanol or isopropanol, butanol, ethylene glycol, propylene glycol or butanediol, glycerol, diethylene glycol, propyl or butyl diethylene glycol, ethylene glycol methyl ether, ethylene glycol ethyl ether, ethylene glycol propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol methyl ether, diethylene glycol ethyl ether, propylene glycol methyl ether, ethyl ether or propyl ether, dipropylene glycol methyl ether or ethyl ether, methoxy, ethoxy or butoxytriethylene glycol, 1-butoxyethoxy-2-propanol, 3-methyl-3-methoxybutanol, or propylene glycol tert-butyl ether. For example, such solvents may be added during preparation steps, such as during steps I and / or II, preferably before step II. Preferably, the organic solvent is ethanol, n-propanol or isopropanol, or propylene glycol, more preferably ethanol or isopropanol.

[0085] In one embodiment of the present invention, the content of organic solvent in the cationic surfactant mixture is 0% to 30%, preferably 0% to 20%, more preferably 10% to 20% (by weight).

[0086] In one embodiment of the invention, the mixture is substantially water-free.

[0087] In one embodiment of the invention, the mixture consists essentially of the reaction products of steps I and II and an optional organic solvent. Preferably, the mixture consists of the reaction products of steps I and II, as well as the solvent (if any), unreacted starting materials, and unavoidable impurities (if any) from the production process.

[0088] Quaternary ammonium ester components

[0089] Quaternary ammonium ester components include one or more quaternary ammonium ester compounds of formula (IV):

[0090]

[0091] in

[0092] X1 represents a hydroxyalkyl group containing 1 to 4 carbon atoms or an alkyl group containing 1 to 4 carbon atoms; preferably, X1 is methyl.

[0093] R7 is a straight-chain or branched C6-C23 alkyl or alkenyl group, preferably C10-C22 alkyl or alkenyl group, more preferably C14-C20 alkyl or alkenyl group, and even more preferably C16-C18 alkyl or alkenyl group.

[0094] R8 and R9 each independently represent -H, -OH, or -O-Tq-C(O)-R7;

[0095] T represents the -(OCH2CH2)a-(OCHR4CH2)b- group, wherein R4 represents an alkyl group containing 1 to 4 carbon atoms, a represents a number in the range of 0 to 20, b represents a number in the range of 0 to 6, and the sum of a+b represents the average degree of alkoxylation corresponding to the number from 0 to 26; preferably 0 to 6, most preferably 0;

[0096] q represents a number in the range 0 to 26;

[0097] m, n, and p each independently represent numbers in the range of 1 to 4, and A represents an anion.

[0098] In one embodiment of the invention, where q is not 0 and a+b is not 0, the quaternary ammonium ester compound of the invention is an ethoxylated and / or propoxylated ester quaternary ammonium salt. The order of the ethylene oxide group and the propylene oxide group is not critical to the invention.

[0099] In a preferred embodiment, the quaternary ammonium ester compound is preferably non-ethoxylated and non-propoxylated.

[0100] In one preferred embodiment, m, n, and p equal 2. In another preferred embodiment, m and p equal 2, and n equals 1.

[0101] Similarly, in a preferred embodiment, q represents a number in the range of 0 to 10, more preferably a number in the range of 0 to 6, and most preferably 0.

[0102] A preferably represents a halogen, phosphate, or alkyl sulfate, more preferably an alkyl sulfate, and most preferably a methyl sulfate.

[0103] In another embodiment, the quaternary ammonium ester component comprises a mixture of at least one or more quaternary ammonium monoester compounds of formula (IV.1), at least one or more quaternary ammonium diester compounds of formula (IV.2), and / or at least one quaternary ammonium triester compound of formula (IV.3):

[0104]

[0105] R8 and R9 each independently represent -H or -OH; and X1, R7, T, a, b, q, m, r, p, and A are as described above.

[0106] In one embodiment of the present invention, the quaternary ammonium ester component is composed of at least one quaternary ammonium monoester compound of formula (IV.1), at least one quaternary ammonium diester compound of formula (IV.2), and at least one quaternary ammonium triester compound of formula (IV.3).

[0107] In another embodiment of the invention, the quaternary ammonium ester component comprises or is composed of at least one quaternary ammonium monoester compound of formula (IV.1), at least one quaternary ammonium diester compound of formula (IV.2), and at least one quaternary ammonium triester compound of formula (IV.3), wherein m=r=p; R7 is a straight-chain alkyl or alkenyl group containing 14 to 20 carbon atoms, preferably derived from (hydrogenated and / or non-hydrogenated) tallow fatty acids, palm fatty acids, oil fatty acids, or mixtures thereof; R8 and R9 each represent -OH, q is 0 (i.e., the compound is not alkoxylated); X1 is methyl; and A- is selected from halogen, phosphate, and alkyl sulfate, preferably alkyl sulfate.

[0108] In another embodiment of the invention, the quaternary ammonium ester component comprises or consists of at least one or more quaternary ammonium monoesters, diesters, or triesters represented by formulas (IV.1), (IV.2), and (IV.3), as defined above, wherein R8 and R9 independently represent -OH; each m, r, p represents the number 2, and X1, R7, T, a, b, q, m, r, p, and A have the meanings described above for formulas (IV.1), (IV.2), and (IV.3).

[0109] In another embodiment of the invention, R7 is a straight-chain or branched alkyl group containing 5 to 23 carbon atoms or a straight-chain alkenyl group containing 5 to 23 carbon atoms and 1 to 3 double bonds; preferably, the alkyl or alkenyl group contains 11 to 21 carbon atoms.

[0110] As used herein, the term "alkyl" refers to a straight-chain or branched hydrocarbon chain containing 1 to 23, preferably 5 to 23, carbon atoms.

[0111] As used herein, the term "alkenyl" refers to a straight-chain hydrocarbon chain containing 2 to 23, preferably 5 to 23, carbon atoms and 1 to 3 unsaturated bonds.

[0112] As used herein, unless otherwise stated, the term "quaternary ammonium ester compound" refers to a quaternized (i.e., cationic) nitrogen-containing species together with their corresponding counterions (i.e. anions) in a molar ratio such that the entire compound is electrically neutral (i.e., the total positive charge of the quaternized nitrogen-containing species is equal to the total negative charge of the counterions).

[0113] Straight-chain or branched alkyl or straight-chain alkenyl groups may be derived from fatty acids or their methyl / triglycerides, or may be alkyl or alkenyl groups derived from oils and fats obtained from tallow, palm, olive, coconut, sunflower, soybean, rapeseed, grape pomace and grape, each of which may be hydrogenated, partially hydrogenated or non-hydrogenated.

[0114] Synthetic fatty acids or their methyl / triglycerides, such as hexanoic acid, caprylic acid, 2-ethylhexanoic acid, decanoic acid, lauric acid, isotretinoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, transoleic acid, phellandrene, linoleic acid, linolenic acid, tung oil acid, arachidic acid, codoleic acid, benzyl acid and erucic acid and mixtures thereof, stearic acid, isostearic acid, palmitic acid, myristic acid, lauric acid, decanoic acid, caprylic acid, 2-ethylhexanoic acid, 2-octyldodecanoic acid, decanoic acid, oleic acid, linoleic acid, linolenic acid, partially hydrogenated coconut fatty acids, palm fatty acids, partially hydrogenated distilled palm fatty acids, hydrogenated distilled palm fatty acids, palm kernel fatty acids, tallow fatty acids, distilled tallow fatty acids and rapeseed fatty acids.

[0115] Preferably, the straight-chain or branched alkyl or straight-chain alkenyl groups are derived from fatty acids derived from palm oil, coconut oil, olive oil, tallow, and hydrogenated tallow.

[0116] The preferred fatty acid is C. 12 -C 22 An acid whose degree of unsaturation results in an iodine value (“IV”) in the range of 0 to 150, preferably 20 to 100, and more preferably 30 to 100.

[0117] As used herein, the term "alkyl or alkenyl derived from a fatty acid" refers to the carbon atom in the alkyl or alkenyl group bonded to the carbonyl group in the respective fatty acid, for example, "derived from C..." 18 "Alkyl group of fatty acids" refers to C17 alkyl group.

[0118] Preparation of quaternary ammonium ester components:

[0119] Quaternary ammonium ester components can be prepared by reacting a fatty acid of formula R12-COOH or a derivative thereof (e.g., its chloride, anhydride or ester) with triethanolamine or methyldiethanolamine or a mixture thereof (preferably triethanolamine).

[0120] Preferably, the compound of formula R12-COOH is a C6-24 fatty acid. The fatty acid can be a natural product obtained from plant and animal oils and fats (e.g., palm, sunflower, soybean, olive, rapeseed, tallow, and tall oil). Alternatively, synthetic fatty acids can be used. Optionally, the fatty acid is fully or partially hydrogenated.

[0121] In one embodiment of the invention, R12 is a straight-chain or branched C6-C24 alkyl or alkenyl group, preferably C10-C22 alkyl or alkenyl group, more preferably C14-C20 alkyl or alkenyl group, and even more preferably C16-C18 alkyl or alkenyl group. Examples of straight-chain or branched alkyl or alkenyl groups are products obtained from oils and fats of plants and animals (e.g., palm, coconut, sunflower, soybean, palm oil extract, olive, rapeseed, tallow, or tallow), which may be wholly or partially hydrogenated and purified, or synthetic fatty acids, such as palmitic acid, oleic acid, transoleic acid, phellandrene, linoleic acid, linolenic acid, cod oleic acid, benzyl acid, and erucic acid, or mixtures thereof. Palm oil, partially hydrogenated palm fatty acids, and oleic acid are preferably used.

[0122] Representative examples of fatty acids that can be used in the methods of the present invention include palmitic acid, oleic acid, tranexamic acid, phellandic acid, linoleic acid, linolenic acid, cod oleic acid, benzolic acid and erucic acid or mixtures thereof.

[0123] The reaction between an alkanolamine or a mixture of alkanolamines and a fatty acid of the formula R12-COOH is an esterification reaction and can be carried out under conditions known in the art, such as those described in patent application ES-A-2021900, the contents of which are incorporated herein by reference.

[0124] The ratio of the fatty acid compound of formula R12COOH or its derivative used in the esterification reaction to an alkanolamine (e.g., triethanolamine) is preferably less than 2.5, more preferably between 1.2 and 2.5. Preferably, the esterification reaction is carried out in the presence of a catalyst such as hypophosphite or p-toluenesulfonic acid. Conventional stabilizers and / or antioxidants (e.g., tocopherol, BHT, BHA, citric acid, etc.) may also be present in the esterification reaction mixture.

[0125] Preferably, the esterification reaction is carried out at a temperature between 120°C and 220°C. Preferably, the reaction time is 2 to 10 hours. Preferably, the reaction is carried out under reduced pressure of up to about 700 mbar. The progress of the reaction can be monitored using conventional techniques (e.g., TLC or HPLC). For example, the consumption of the R1COOH compound during the reaction can be monitored.

[0126] The quaternization of the esterification products of alkanolamines and fatty acids is carried out in a known manner, for example, as described in WO9101295. Preferably, the alkylating agent includes, but is not limited to, chloromethane, dimethyl sulfate, or mixtures thereof.

[0127] Quaternization can be carried out in bulk or in a solvent, within a temperature range of 40°C to 100°C. If a solvent is used, the starting material and / or product must be soluble in the solvent to the extent required for the reaction. The composition obtained by the quaternization process comprises a quaternized ammonium ester compound having one (monoester), two (diester), or three (triester) ester groups. The product may also contain a quaternized alkanolamine and a small amount of unreacted fatty acid.

[0128] Quaternary ammonium ester components can be generated in situ during the reaction process to prepare a mixture of cationic surfactants.

[0129] Methods for dispersing quaternary ammonium ester components:

[0130] Another aspect of the invention is a method for dispersing a quaternary ammonium ester component in water, the quaternary ammonium ester component comprising one or more compounds of formula (IV) as previously defined, the method comprising the steps of: (i) mixing one or more compounds of formula (IV) with a cationic mixture as defined above, (ii) adding water, and (iii) mixing. All embodiments of mixtures involving cationic surfactants and ammonium components provided above are also embodiments of this dispersion method.

[0131] The mixing in steps (i) and (iii) can be carried out by any suitable method, such as stirring with a stirrer or by hand. In one embodiment, the mixture of cationic surfactants and the quaternary ammonium ester component are mixed under continuous stirring, preferably at a temperature of 10°C to 80°C, more preferably 20°C to 60°C, and more preferably 20°C to 40°C.

[0132] Steps (ii) and (iii) can be performed sequentially or simultaneously.

[0133] In a preferred embodiment, the method of dispersing the quaternary ammonium ester component in water includes the additional step of adding a fragrance; particularly, the fragrance is added before adding water.

[0134] Composition

[0135] A composition, preferably a fabric softener and / or a keratin-based fiber softener composition, is also provided, comprising at least a mixture of cationic surfactants according to the invention and a quaternary ammonium ester compound. All embodiments provided above regarding the mixture of cationic surfactants and the ammonium component are also embodiments of the compositions of the invention.

[0136] In one embodiment of the invention, the weight ratio between the cationic surfactant mixture and the quaternary ammonium ester component is 10:90 to 70:30, preferably 20:80 to 60:40, and more preferably 30:70 to 50:50. Depending on the reaction conditions, some of the quaternary ammonium ester component can be generated in situ during the reaction process to prepare the cationic surfactant mixture, thus affecting the weight ratio of the components. Those skilled in the art can adjust the weight ratio accordingly.

[0137] In another embodiment of the invention, the iodine value of the mixture of cationic surfactants and the quaternary ammonium ester component is 0 to 100, preferably 20 to 80, and more preferably 30 to 50.

[0138] In one embodiment of the invention, the composition further comprises a fragrance.

[0139] The fragrance is composed of one or more substances. The ClogP of the fragrance substance (one or more) is 0.5 to 8, preferably 2 to 7. The weight ratio between the mixture of cationic surfactant and quaternary ammonium ester compound as defined above and the fragrance is 99:1 to 40:60, preferably 95:5 to 50:50, more preferably 95:5 to 70:30.

[0140] In one embodiment of the invention, the mixture of fragrance with cationic surfactant and quaternary ammonium ester compound is a clear viscous liquid that can be directly and easily dispersed in water, wherein such diluted formulation is stable during storage.

[0141] Compositions containing a mixture of cationic surfactants, quaternary ammonium ester components, and fragrances can be carried out by stirring, particularly under continuous stirring, at a temperature of 5°C to 40°C, preferably 10°C to 30°C, and more preferably 15°C to 25°C.

[0142] The composition preferably also contains water.

[0143] In another embodiment, the composition is a dispersion.

[0144] The present invention also provides a method for obtaining the compositions of the present invention, the method comprising mixing a mixture of cationic surfactants, a quaternary ammonium ester component, and optionally a fragrance. Alternatively, the present invention provides a composition obtainable by the methods provided herein.

[0145] In one embodiment, when the composition is a dispersion, the method includes mixing a mixture of cationic surfactants, a quaternary ammonium ester component, and a fragrance, and then dispersing the composition with water. Specifically, the method includes (i) mixing the mixture of cationic surfactants and the ammonium component, (ii) adding the fragrance to the mixture obtained in step (i), (iii) adding water, and (iv) stirring, particularly continuously. In one embodiment of the invention, the water temperature is 5°C to 40°C, preferably 10°C to 30°C, more preferably 15°C to 25°C.

[0146] On the other hand, the present invention provides a dispersion composition that can be obtained by any of the methods provided herein.

[0147] In one embodiment of the invention, the water content of the composition is preferably higher than 50 wt%, more preferably higher than 80 wt%, and most preferably higher than 85 wt%, based on the total weight of the softener composition. The solid residue is preferably lower than 50 wt%, more preferably lower than 25 wt%, and even more preferably between 2 wt% and 15 wt%, based on the total weight of the softener composition.

[0148] In a preferred embodiment of the invention, the composition is a dispersion and comprises a mixture of cationic surfactants, a quaternary ammonium ester component, a fragrance, and water, wherein the water hardness value is 0 ppm to 800 ppm CaCO3, 0 ppm to 600 ppm CaCO3, 0 ppm to 400 ppm CaCO3, 0 ppm to 200 ppm CaCO3, 5 ppm to 800 ppm CaCO3, 5 ppm to 600 ppm CaCO3, 5 ppm to 400 ppm CaCO3, 5 ppm to 200 ppm CaCO3, 10 ppm to 800 ppm CaCO3, 10 ppm to 600 ppm CaCO3, 10 ppm to 400 ppm CaCO3, or 10 ppm to 200 ppm CaCO3. In a particular embodiment, the water is deionized water. In another embodiment, the water is tap water.

[0149] Water hardness can be defined as the concentration of calcium and magnesium ions in water, expressed as calcium carbonate. Deionized water is water that has been treated to have a hardness of 0 ppm CaCO3 or less (preferably less than 3 ppm CaCO3), while tap water, which is available in homes, typically has a hardness value of 10 ppm to 400 ppm CaCO3.

[0150] Water hardness can be measured according to UNE-EN-12829.

[0151] In another embodiment of the invention, the composition further comprises a thickener, such as a thickening polymer. The weight ratio of the cationic surfactant mixture to the thickener is preferably 150:1 to 10:5, more preferably 100:1 to 10:2. A thickener may be added to increase the viscosity of the composition. Suitable thickeners are, for example, PEG-150 distearate, hydroxyethyl cellulose, hydroxymethyl cellulose and their derivatives, PEG-120 methyl glucose dioleate, PEG-120 methyl glucose trioleate, (and) propylene glycol, and ethoxylated sorbitol triisostearate (e.g., PEG-160 sorbitol triisostearate, such as Kaopan TW IS-559S from Kao Chemicals Europe Ltd.), and copolymers of acrylamide and dimethylaminoethyl methacrylate chloromethane crosslinked with methylenebisacrylamide (e.g., FLOSOFT 222 manufactured by SNF).

[0152] Advantageously, mixtures of cationic surfactants can disperse quaternary ammonium ester components (one or more) that form part of fabric softeners and / or keratin-based fiber softeners. As shown below, the resulting softener dispersions exhibit improved stability during long-term storage. This indicates that, in the context of this invention, cationic mixtures provide a significant dispersing effect: the remaining components forming part of the softening composition, such as fragrances, have no negative impact on the dispersing effect.

[0153] In another embodiment, the viscosity of the composition at 20°C can be from 5 cps to 500 cps, as measured on a Brookfield LVT viscometer with a rotating shaft 2 at 60 rpm.

[0154] Preferably, the softener composition exhibits favorable storage stability.

[0155] In one embodiment of the invention, the softener composition is stable for at least 2 months, preferably at least 3 months, and more preferably at least 6 months when stored in a temperature range of 5°C to 40°C, preferably 10°C to 30°C, and more preferably 15°C to 25°C.

[0156] In another embodiment of the invention, the softener composition is stable for at least three months, wherein the mixture of cationic surfactants is characterized by a molar ratio of monocarboxylic acid / diacarboxylic acid (b1 / b2) of 1.5 to 4.0, an equivalence ratio (COOH / OH) between organic carboxylic acid groups and organic hydroxyl groups of 0.5 to 0.7, and a molar ratio between compounds (one or more) defined in a.2 and compounds defined in a.1 of 0; wherein the quaternary ammonium ester component comprises or consists of at least one quaternary ammonium monoester compound of formula (IV.1) and at least one quaternary ammonium diester compound of formula (IV.2). The compound consists of an ester compound and at least one quaternary ammonium triester compound of formula (IV.3), wherein m=r=p; R7 is a straight-chain alkyl or alkenyl group containing 16 to 18 carbon atoms, preferably derived from hydrogenated and / or non-hydrogenated tallow fatty acids, oleic fatty acids or palm fatty acids; R8 and R9 each represent -OH, q is 0 (i.e. the compound is non-alkoxylated); X1 is methyl; and A- is selected from halogen, phosphate and alkyl sulfate, preferably alkyl sulfate; and the weight ratio between the mixture of cationic surfactants and the quaternary ammonium ester compound is 30:70 to 50:50.

[0157] In another embodiment of the invention, the softener composition is stable for at least three months, and the mixture of cationic surfactants is characterized by a molar ratio of monocarboxylic acid / diacarboxylic acid (b1 / b2) of 1.5 to 4.0, an equivalence ratio of organic carboxylic acid groups to organic hydroxyl groups (COOH / OH) of 0.5 to 0.7, and a molar ratio of one or more compounds defined in a.2 to compounds defined in a.1 of 0; wherein the quaternary ammonium ester component comprises or consists of at least one quaternary ammonium monoester compound of formula (IV.1), at least one quaternary ammonium diester compound of formula (IV.2), and at least one quaternary ammonium triester compound of formula (IV.3). The composition includes m=r=p; R7 is a straight-chain acyl group, wherein R1 is a straight-chain alkyl or straight-chain alkenyl group containing 16 to 18 carbon atoms, preferably derived from hydrogenated and / or non-hydrogenated tallow fatty acids, oleic fatty acids, or palm fatty acids; R8 and R9 each represent -OH, q is 0 (i.e., the compound is non-alkoxylated); X1 is methyl; and A- is selected from halogens, phosphates, and alkyl sulfates, preferably alkyl sulfates; and the weight ratio between the cationic surfactant mixture and the quaternary ammonium ester component is 30:70 to 50:50; and wherein the cationic surfactant mixture and the quaternary ammonium ester component are mixed with the fragrance before being dispersed in water.

[0158] In one embodiment of the present invention, the softener dispersion composition comprises:

[0159] -Based on the total weight of the softener composition, a mixture of the cationic surfactant and quaternary ammonium ester components described above, comprising 3 wt% to 20 wt%, preferably 5 wt% to 15 wt%, more preferably 5 wt% to 12 wt%;

[0160] -Based on the total weight of the softener composition, 0.2 wt% to 5 wt%, preferably 0.3 wt% to 3 wt%, more preferably 0.5 wt% to 2 wt% of fragrance; and

[0161] -0 wt% to 1.0 wt%, preferably 0 wt% to 0.5 wt% of thickener.

[0162] In one embodiment of the invention, the fabric softener composition further comprises optional components.

[0163] When referring to optional components, it should not be regarded as an exhaustive description of all possibilities; on the other hand, as is well known to those skilled in the art, the following can be mentioned:

[0164] a) Other products that enhance the properties of the softener composition, such as silicones, amine oxides, anionic surfactants (e.g., lauryl ether sulfate or lauryl sulfate), amphoteric surfactants (e.g., cocamidopropyl betaine or alkyl betaine), sulfosuccinates, polyglucoside derivatives, etc.

[0165] b) Stable products, such as short-chain amine salts, whether quaternized or non-quaternized, such as triethanolamine, N-methyldiethanolamine, etc., and nonionic surfactants, such as ethoxylated fatty alcohols and ethoxylated fatty amines.

[0166] c) Products that improve viscosity control, such as inorganic salts like calcium chloride, magnesium chloride, calcium sulfate, sodium chloride, etc.; products that can be used to reduce the viscosity of concentrated compositions, such as glycol compounds like ethylene glycol, dipropylene glycol, polyethylene glycol, etc.; thickeners for diluting compositions, such as polymers, preferably water-soluble or water-dispersible polymers, and preferably cationic polymers. Suitable cationic polymers include cationic guar gum polymers, cationic cellulose derivatives, cationic potato starch, and cationic polyacrylamide. Crosslinked, water-swellable cationic polymers are particularly suitable. These described polymers can also be used as deposition aids.

[0167] d) Components for adjusting pH, with a pH of 2.0 to 6.0, preferably 2.5 to 4.0, such as any type of inorganic acid and / or organic acid, such as hydrochloric acid, sulfuric acid, phosphoric acid, lactic acid, citric acid, etc.

[0168] e) Agents that improve stain resistance, such as known polymers or copolymers based on terephthalates.

[0169] f) Preservatives, such as bactericides, such as 1,2-benzisothiazolin-3-one, 5-chloro-2-methyl-4-isothiazolin-3-one and 2-methyl-4-isothiazolin-3-one or combinations thereof, 2-bromo-2-nitropropane-1,3-diol, etc.

[0170] g) Other products, such as antioxidants, colorants, fragrances, bactericides, fungicides, corrosion inhibitors, anti-wrinkle agents, opacifiers, fluorescent whitening agents, pearlescent agents, etc.

[0171] h) Encapsulated fragrance, which can be added to the softener composition after being dispersed in water.

[0172] Concentrated composition suitable for consumers to disperse in cold water at home

[0173] The present invention also provides a concentrated softener composition comprising a mixture of cationic surfactants as described above and a quaternary ammonium ester compound, and having a water content of less than 50 wt%, preferably less than 30 wt%, more preferably less than 10 wt%, even more preferably less than 5 wt%, less than 4 wt%, less than 3 wt%, less than 2 wt%, less than 1 wt%; even more preferably less than 1 wt%; or as low as 0.1 wt%.

[0174] In one embodiment of the invention, the concentrated softener composition further comprises a fragrance, preferably wherein the average ClogP of the fragrance substance (one or more) is 0.5 to 8, preferably 2 to 7.

[0175] In another embodiment, the weight ratio of the mixture of the cationic surfactant and the quaternary ammonium ester compound as defined above to the fragrance is 99:1 to 40:60, preferably 95:5 to 50:50, and more preferably 95:5 to 70:30.

[0176] In another embodiment of the invention, the mixture of the fragrance with the composition comprising a mixture of cationic surfactants and a quaternary ammonium ester component is a clear viscous liquid that can be directly and easily dispersed in water, wherein such preparations are stable during storage.

[0177] In a preferred embodiment, the present invention provides the use of a mixture of cationic surfactants for dispersing a quaternary ammonium ester component to prepare a concentrated fabric softener composition suitable for preparing a household fabric softener formulation by dilution with water, wherein the composition also contains fragrance. Such compositions are preferably liquid at temperatures from 5°C to 80°C, preferably from 10°C to 60°C, more preferably from 15°C to 40°C, and even more preferably from 15°C to 25°C; they contain a mixture of cationic surfactants as described above and a quaternary ammonium ester compound, and the water content is less than 50 wt%, preferably less than 30 wt%, more preferably less than 10 wt%, and even more preferably less than 5 wt%, less than 1 wt%.

[0178] In another embodiment, the concentrated softener composition can be dispersed in water at a low temperature of 5°C to 40°C, preferably 10°C to 30°C, and more preferably 15°C to 25°C.

[0179] In another embodiment, the concentrated softener composition may be dispersed in tap water (e.g., water obtained directly from a tap or stopcock connected to the main local water supply system) that is not distilled and / or deionized.

[0180] In another embodiment, the concentrated softener composition can be dispersed in water, wherein the water hardness value is 0 ppm to 800 ppm CaCO3, 0 ppm to 600 ppm CaCO3, 0 ppm to 400 ppm CaCO3, 0 ppm to 200 ppm CaCO3, 5 ppm to 800 ppm CaCO3, 5 ppm to 600 ppm CaCO3, 5 ppm to 400 ppm CaCO3, 5 ppm to 200 ppm CaCO3, 10 ppm to 800 ppm CaCO3, 10 ppm to 600 ppm CaCO3, 10 ppm to 400 ppm CaCO3, or 10 ppm to 200 ppm CaCO3.

[0181] Preferably, such compositions exhibit favorable storage stability.

[0182] In one embodiment of the invention, the concentrated softener composition dispersed in water is stable for at least 2 months, preferably at least 3 months, and more preferably at least 6 months when stored in a temperature range of 5°C to 40°C, preferably 10°C to 30°C, and more preferably 15°C to 25°C.

[0183] In another embodiment of the invention, a mixture of cationic surfactants is used to disperse a quaternary ammonium ester compound for use in preparing a concentrated fabric softener composition suitable for dispersibility in cold water by a consumer at home, wherein the resulting composition is stable for at least three months, wherein, in the definition of a cationic mixture, the molar ratio of a monocarboxylic acid to a dicarboxylic acid (b1 / b2) is 1.5 to 4.0, the equivalence ratio of an organic carboxylic acid group to an organic hydroxyl group (COOH / OH) is 0.5 to 0.7, and the molar ratio of one or more compounds defined in a.2 to the compounds defined in a.1 is 0; wherein the quaternary ammonium ester compound comprises or is composed of at least one quaternary ammonium monocarboxylic acid of formula (IV1). The compound comprises an ester compound, at least one quaternary ammonium diester compound of formula (IV2) and at least one quaternary ammonium triester compound of formula (IV3), wherein m=r=p; R7 is a straight-chain acyl group, wherein R7 is a straight-chain alkyl or straight-chain alkenyl group containing 16 to 18 carbon atoms, preferably derived from (hydrogenated and / or non-hydrogenated) tallow fatty acids, oleic fatty acids or palm fatty acids; R8 and R9 each represent -OH, q is 0 (i.e. the compound is non-alkoxylated); X1 is methyl; and A- is selected from halogen, phosphate and alkyl sulfate, preferably alkyl sulfate; and the weight ratio between the mixture of cationic surfactants and the quaternary ammonium ester compound is 30:70 to 50:50.

[0184] In another embodiment of the invention, a mixture of cationic surfactants is used to disperse quaternary ammonium ester compounds to prepare concentrated fabric softener compositions suitable for dispersibility in cold water by consumers at home, wherein the resulting compositions are stable for at least three months, wherein, in the definition of a cationic mixture, the molar ratio of monocarboxylic acid / diacarboxylic acid (b1 / b2) is 1.5 to 4.0, the equivalence ratio between organic carboxylic acid groups and organic hydroxyl groups (COOH / OH) is 0.5 to 0.7, and the molar ratio between compounds (one or more) defined in a.2 and compounds defined in a.1 is 0; wherein the quaternary ammonium ester compounds comprise or consist of at least one quaternary ammonium monoester compound of formula (IV1), The composition comprises at least one quaternary ammonium diester compound of formula (IV2) and at least one quaternary ammonium triester compound of formula (IV3), wherein m=r=p; R7 is a straight-chain acyl group, wherein R7 is a straight-chain alkyl or straight-chain alkenyl group containing 16 to 18 carbon atoms, preferably derived from (hydrogenated and / or non-hydrogenated) tallow fatty acids, oleic fatty acids or palm fatty acids; R8 and R9 each represent -OH, q is 0 (i.e. the compound is non-alkoxylated); X1 is methyl; and A- is selected from halogen, phosphate and alkyl sulfate, preferably alkyl sulfate; the weight ratio between the mixture of cationic surfactants and the quaternary ammonium ester compound is 30:70 to 50:50, and the concentrated softener composition further comprises fragrance.

[0185] In another embodiment of the composition, the concentrated softener composition may have a viscosity of 200 cps to 50,000 cps at 20°C, as measured on a Brookfield LVT viscometer with shaft 2 at 60 rpm or shaft 4 at 12 rpm. Preferably, such compositions are non-Newtonian and have a viscosity of 200 mPas to 5,000 mPas, as measured on a Brookfield LVT viscometer with shaft 4 at 12 rpm, optionally 200 mPas to 800 mPas; or are Newtonian and have a viscosity of 200 mPas to 800 mPas, as measured on a Brookfield LVT viscometer with shaft 2 at 30 rpm.

[0186] In another embodiment of the invention, the concentrated composition further comprises an encapsulated fragrance, which is different from the fragrance described above. Preferably, the fragrance is encapsulated in biodegradable microcapsules, more preferably, the microcapsules are chitosan-based.

[0187] use:

[0188] The present invention provides the use of a mixture of cationic surfactants as described above for dispersing quaternary ammonium ester components for use in softener compositions.

[0189] Specifically, the present invention provides the use of a mixture of cationic surfactants available as described above for dispersing a quaternary ammonium ester component forming part of a softener composition in water, wherein the softener composition exhibits improved stability when stored for at least three months in a temperature range of 5°C to 40°C, preferably 10°C to 30°C, and more preferably 15°C to 25°C.

[0190] This application includes dispersing a mixture of cationic surfactants and quaternary ammonium ester components, and preferably fragrances, in water, wherein the water hardness values ​​are 0 ppm to 800 ppm CaCO3, 0 ppm to 600 ppm CaCO3, 0 ppm to 400 ppm CaCO3, 0 ppm to 200 ppm CaCO3, 5 ppm to 800 ppm CaCO3, 5 ppm to 600 ppm CaCO3, 5 ppm to 400 ppm CaCO3, 5 ppm to 200 ppm CaCO3, 10 ppm to 800 ppm CaCO3, 10 ppm to 600 ppm CaCO3, 10 ppm to 400 ppm CaCO3, and 10 ppm to 200 ppm CaCO3.

[0191] In another embodiment of the invention, the use includes: dispersing a mixture of cationic surfactants and quaternary ammonium ester compounds, and preferably fragrances, in water to obtain a softener composition, and then including the step of contacting the mixture with fabrics and / or fibers.

[0192] In one embodiment of the invention, a method for conditioning textiles includes the steps of: contacting one or more textile articles with the fabric softener composition of the invention at one or more points during a washing process, and drying the textile articles by means of drying them with a mechanical roller.

[0193] The use of the fabric conditioning composition of the present invention for conditioning treatment of textiles is another embodiment of the present invention.

[0194] As used herein, a stable softener composition is one that, upon preparation and after storage, maintains the same or minimally changed appearance, color, viscosity, and any other parameters of the initial dispersion for a certain time interval. Preferably, the composition is stable for at least 2 months, more preferably at least 3 months, and more preferably at least 6 months.

[0195] In one embodiment of the invention, a stable softener composition refers to a composition that maintains its viscosity for a certain time interval after preparation and after storage. Preferably, the composition is stable for at least 2 months, more preferably at least 3 months, and even more preferably at least 6 months.

[0196] In the context of this invention, a stable composition that “maintains its viscosity over a certain time interval” encompasses a viscosity value that varies by up to ±10%, up to ±9%, up to ±8%, up to ±7%, up to ±6%, up to ±5%, up to ±4%, up to ±3%, up to ±2%, or up to ±1% immediately after the composition is prepared.

[0197] As used herein, when the ratio (e.g., molar ratio) "x / y" between compounds (one or more) within the first definition "x" and compounds (one or more) under the second definition "y" is 0, this means that compounds within the first definition "x" are absent or substantially absent.

[0198] As used herein, viscosity is measured at 20°C using a Brookfield LVT viscometer with shaft 2 at 30 rpm or 60 rpm (preferably for low viscosity) or shaft 4 at 12 rpm (preferably for high viscosity).

[0199] As used herein, the "iodine number" (or "iodine value," or "iodine adsorption value," commonly abbreviated as IV) describes the degree of unsaturation, such as that of fatty acids, and can be determined according to EN 14111:2003. The iodine value is the mass (in grams) of iodine consumed by 100 grams of a chemical substance or composition. The iodine value is commonly used to determine the amount of unsaturation in fats, oils, and waxes. Therefore, the iodine value is suitable for determining the degree of unsaturation of the carboxylic acids of this invention.

[0200] In the context of this invention, the iodine value can be calculated from the original source of the fatty acid (i.e., carboxylic acid) or measured from a composition as defined above (comprising a mixture of cationic surfactants and a quaternary ammonium ester component).

[0201] As used herein, “room temperature” is understood to be a temperature of 5°C to 40°C, preferably 10°C to 30°C.

[0202] As used herein, “cold water” is understood to be water with a temperature of 5°C to 40°C, preferably 10°C to 30°C, and more preferably 15°C to 25°C.

[0203] As used herein, "tap water" is understood to be non-deionized water, i.e., water that does not contain dissolved minerals. Mineral content is expressed as water hardness, quantified in ppm (parts per cubic centimeter) of CaCO3. For deionized water, a CaCO3 content of 0 ppm or less, preferably less than 3 ppm, is considered to be deionized water.

[0204] As used herein, "dispersion" is understood to mean the formation of a dispersion, i.e., a system in which particles of one material are uniformly distributed within a continuous phase of another material, thereby allowing the formation of a colloidal or suspension. In this invention, a mixture of cationic surfactants and a quaternary ammonium ester component are uniformly distributed in water to obtain a dispersion. The final appearance is considered to be an opaque, homogeneous, and liquid dispersion.

[0205] As used herein, fabrics—textile materials—include materials such as natural, synthetic, and man-made fibers. Natural fibers include plant fibers, such as cotton, or keratin fibers (wool, silk). Some common man-made fibers are polyester, polyamide, acrylic, modal, polyurethane, viscose, and blends thereof.

[0206] In this article, ClogP refers to the calculated octanol / water partition coefficient (P) of a flavoring component, expressed as a logarithm to base 10. The octanol / water partition coefficient of a flavoring component is the ratio between its equilibrium concentration in octanol and in water.

[0207] LogP values ​​for many flavoring components have been reported; for example, the Pomona92 database, available from Daylight Chemical Information Systems, Inc. (Daylight CIS), Irvine, Calif., contains numerous such values ​​along with citations of the original literature. Clog values ​​can be calculated using fragment methods, as described by A. Leo, C. Hansch, and DElkins in “Partition Coefficients and Their Uses” in Chem. Rev. vol 71 (6) pages 525-616 (1971). Alternatively, Clog values ​​can also be calculated using the “CLOGP” program available in Chemoffice Ultra Software version 9, available from CambridgeSoft Corporation, 100 CambridgeParkDrive, Cambridge, MA 02140 USA or CambridgeSoft Corporation, 8 Signet Court, Swans Road, Cambridge CB5 8LA UK. Alternatively, ClogP values ​​can also be calculated in the US EPA CompTox Chemicals Dashboard (https: / / comptox.epa.gov / dashboard, v2.2.1).

[0208] Example:

[0209] The following embodiments are provided to give those skilled in the art a sufficiently clear and complete explanation of the invention, but should not be considered as limitations on the basic aspects of the subject matter of the invention as described in the preceding parts of this specification.

[0210] The first part of the Examples section relates to the preparation of mixtures of cationic surfactants and quaternary ammonium ester compositions according to the present invention.

[0211] Part Two relates to the preparation of the fabric softener composition according to the invention and the determination of the dispersion stability.

[0212] Example 1: Synthesis Steps

[0213] Preparation of a mixture of cationic surfactants (compound A):

[0214] Esterification reaction:

[0215] Under an inert atmosphere, 408.0 g (1.50 mol) of tallow fatty acid (iodine value = 50), 447.0 g (3.00 mol) of triethanolamine, and 219.2 g (1.50 mol) of adipic acid were introduced into a glass reactor with stirring. The mixture was heated at 160°C to 180°C for at least 4 hours to remove water from the reaction. The endpoint of the reaction was monitored by acid value determination until the value was below 4 mg KOH / g.

[0216] A yellow liquid product from the esterification reaction is obtained, which is essentially composed of unesterified fatty acids and adipic acid, triethanolamine monoesterified, diesterified and triesterified with fatty acids, triethanolamine monoesterified, diesterified and triesterified with adipic acid, or combinations thereof, and a mixture of unreacted triethanolamine.

[0217] Quaternization: 142.8 g (2.37 mol) of 2-propanol was added to 943.7 g of the product from the esterification step (containing 2.85 mol of the esterified product) under stirring. Then, 341.4 g (2.71 mol) of dimethyl sulfate was added under stirring at a temperature of 50°C to 90°C. After 4 hours of digestion, the absence of amine was confirmed by acid / base assay. A final product of 1405.1 g was obtained.

[0218] calculate:

[0219] Molar ratio of monocarboxylic acid to dicarboxylic acid:

[0220] 1.50 moles of tallow fatty acid / 1.50 moles of adipic acid = 1.0

[0221] COOH / OH equivalent ratio:

[0222] (1 equivalent * 1.50 moles of tallow fatty acid + 2 equivalents * 1.50 moles of adipic acid) / (3 equivalents * 3.0 moles of triethanolamine) = 0.50

[0223] Preparation of quaternary ammonium ester compound (compound B)

[0224] Esterification reaction:

[0225] Under an inert atmosphere, 1144.9 g (4.06 mol) of oleic fatty acid and 351.7 g (2.36 mol) of triethanolamine were introduced into a glass reactor with stirring. The mixture was heated at 160°C to 180°C for at least 4 hours to remove water from the reaction. The endpoint of the reaction was monitored by acid value determination until the value was below 4 mg KOH / g.

[0226] A yellow liquid product from the esterification reaction is obtained, which is essentially a mixture of unesterified fatty acids, monoesterified, diesterified, and triesterified triethanolamine.

[0227] Quaternization:

[0228] 182.0 g (3.03 mol) of 2-propanol was added to 1368.9 g of the product from the esterification step (containing 2.27 mol of esterified product) under stirring. Then, 269.1 g (2.14 mol) of dimethyl sulfate was added under stirring at a temperature of 50°C to 90°C. After digestion for 4 hours, the absence of amine was confirmed by acid / base assay. 1802.1 g of final product was obtained.

[0229] Example 2: Preparation of fabric softener composition

[0230] Example A (according to the present invention)

[0231] A mixture of compound A and compound B:

[0232] 1000 g of compound A was added to a jacketed glass container at 50°C to 60°C, along with 1000 g of compound B. The iodine value of the mixture was 39. After mixing for 5 minutes, the product was drained, yielding 1978.7 g.

[0233] Preparation of mixtures with spices:

[0234] Add 94.4 g of the mixture of compounds A and B to a container at room temperature with appropriate stirring. Add 15 g of fragrance (commercially available standard fabric softener fragrance for blue line products, available from Kao Chemicals Europe) to the container with stirring. Stir the mixture at room temperature for 5 minutes. Obtain a clear, homogeneous, and viscous mixture.

[0235] Preparation of fabric softener:

[0236] 450 g of water (water hardness 20°fH = 200 ppm CaCO3) was added to a container while stirring at 150 rpm. 50 g of the mixture prepared above was then added to the water while continuing to stir. An opaque dispersion was obtained within 15 seconds. Subsequently, the stability of the dispersion was studied based on several studies of its viscosity.

[0237] Table 1 shows the dispersion time and stability results of the softener compositions of the present invention. Complete dispersion was achieved using the compositions of the present invention (Example A), with the dispersion obtained in less than 15 seconds. Furthermore, the resulting dispersion was found to be stable over extended periods at different temperatures (showing little or no change in viscosity).

[0238]

[0239] Viscosity was measured using a Brookfield LVT viscometer with shaft 2 at 60 rpm.

[0240] The viscosity differences at different times (24 hours, 28 hours, 56 days, 84 days) were not significant.

[0241] Example B (Comparative Example)

[0242] Preparation of mixtures with spices:

[0243] Add 94.4 g of compound B to a container at room temperature with appropriate stirring. Add 15 g of fragrance (commercially available standard fabric softener fragrance for blue line products, available from Kao Chemicals Europe) to the container with stirring. Stir the mixture at room temperature for 5 minutes. Obtain a clear, homogeneous, and viscous mixture.

[0244] Preparation of fabric softener:

[0245] Add 450 g of water (water hardness 20°fH = 200 ppm CaCO3) to the container while stirring at 150 rpm. Continue stirring, then add 50 g of the mixture prepared above to the water. Even after stirring for 5 minutes, a paste-like viscous product is still obtained.

[0246] The inventors discovered that, under the same conditions necessary for preparing the dispersion of the present invention (Example A), it is impossible to obtain a dispersion; instead, a viscous paste-like substance is obtained. This demonstrates the remarkable effect of a mixture of cationic surfactants in dispersing quaternary ammonium ester components.

Claims

1. A mixture of cationic surfactants for use in dispersing at least a quaternary ammonium ester component in water, said mixture of cationic surfactants being obtainable by a method comprising the following steps: Step I: esterification reactions a) and b), and Step II: A cation is formed from the reaction product of Step I, wherein: a) is a hydroxyl-containing compound or a mixture of hydroxyl-containing compounds, comprising a.1 and optionally a.2, wherein: - a.1 is an alkanolamine or a mixture of alkanolamines of general formula (I): R1 is selected from hydrogen, C1-C6 alkyl groups, and residues. R2 is a C1-C6 alkylene group, R3 is hydrogen or methyl, and n is 0 or an integer from 1 to 20; and - a.2 is a polyol, which is optionally alkoxylated, and is characterized by a molecular weight (MW) in the range of 60 g / mol to 190 g / mol; b) is a mixture of compounds containing one or more carboxyl groups, comprising b.1 and b.2, wherein: - b.1 is a monocarboxylic acid or a mixture of monocarboxylic acids of formula (II): R6-COOH (II) Wherein R6 is a straight-chain or branched C6-C23 alkyl or alkenyl group; or an alkyl ester or glycerol ester thereof, preferably a straight-chain or branched C6-C23 alkyl or alkenyl ester; and - b.2 is a dicarboxylic acid or a mixture of dicarboxylic acids of general formula (III), or a reactive derivative thereof: HOOC-L-COOH (III) Wherein L is a saturated or unsaturated straight-chain or branched group having 1 to 10 carbon atoms, or a cyclic group having 3 to 10 carbon atoms, each carbon atom optionally substituted with a C1-C6 saturated or unsaturated group; and preferably (CH(R11)). m Or alternatively replaced by one or more R11 (C6-C 10 (aryl) indicates that each R11 is independently a hydrogen, OH or C1-C6 saturated or unsaturated group, m is an integer from 0 to 10, wherein for m≥2, the chain (CH)m optionally contains one or more double bonds and / or cyclic groups; Where a.1), a.2), b.1), and b.2) are introduced into the reaction system of step I in the following molar ratios: - The molar ratio of monobasic acid to dibasic acid (b.1 / b.2) is 0.3 to 5.0; - The equivalence ratio (COOH / OH) of the organic carboxylic acid groups to organic hydroxyl groups present in the system is 0.4 to 0.8; - The molar ratio between compounds defined in a.2 and compounds defined in a.1 is 0 to 0.5; The quaternary ammonium ester component comprises one or more compounds of formula (IV): in, X1 indicates a hydroxyalkyl group containing 1 to 4 carbon atoms or an alkyl group containing 1 to 4 carbon atoms; R7 is a straight-chain or branched C6-C23 alkyl or alkenyl group; R8 and R9 each independently represent -H, -OH, or -O-Tq-C(O)-R7; T represents the -(OCH2CH2)a-(OCHR4CH2)b- group, where R4 represents an alkyl group containing 1 to 4 carbon atoms, a represents an average number in the range of 0 to 20, b represents an average number in the range of 0 to 6, and the sum of a+b represents the average degree of alkoxylation corresponding to a number in the range of 0 to 26, preferably 0 to 6, and most preferably 0. q represents the average number in the range of 0 to 26; m, r, and p each independently represent the average number in the range of 1 to 4, and A represents an anion, preferably a halide, phosphate, or alkyl sulfate.

2. The use according to claim 1, wherein compounds a.1, a.2, b.1, and b.2 are introduced into the reaction system of step I in the following molar ratio: - The molar ratio of monobasic acid to dibasic acid (b.1 / b.2) is 0.6 to 4.0, preferably 1.5 to 4.0; - The equivalence ratio (COOH / OH) of the organic carboxylic acid groups to organic hydroxyl groups present in the system is 0.5 to 0.7; - The molar ratio between compounds defined in a.2 and compounds defined in a.1 is 0.

3. The use according to any one of the preceding claims, wherein said compound of formula (IV) is a compound of the following: - m, r, and p equal 2; and / or - q is 0; and / or - R7 is a straight-chain or branched alkyl or alkenyl group containing 6 to 23 carbon atoms and 0 to 3 double bonds.

4. The use according to any one of the preceding claims, for dispersing a quaternary ammonium ester compound comprising at least one quaternary ammonium monoester compound of formula (IV.1), at least one quaternary ammonium diester compound of formula (IV.2), and at least one quaternary ammonium triester compound of formula (IV.3) in water: R8 and R9 each independently represent -H or -OH, and X1, R7, T, a, b, q, m, r, p, and A are as defined in any of the preceding claims.

5. The use according to any one of the preceding claims, wherein the weight ratio between the mixture of the cationic surfactant and the quaternary ammonium ester component is 10:90 to 70:30, preferably 20:80 to 60:40, more preferably 30:70 to 50:

50.

6. A method for dispersing a quaternary ammonium ester component in water, said quaternary ammonium ester component comprising one or more compounds of formula (IV) as defined in any one of the preceding claims, said method comprising the steps of: (i) mixing one or more of the compounds of formula (IV) with the cationic mixture as defined in any of the preceding claims, (ii) adding water, and (iii) stirring.

7. The method of claim 6, wherein the method includes an additional step of adding a flavoring; specifically, the flavoring is added before adding water.

8. A composition comprising the cationic mixture as defined in any one of claims 1 to 5 and the quaternary ammonium ester component.

9. The composition according to claim 8, wherein the composition further comprises a fragrance.

10. The composition according to any one of claims 8 to 9, wherein the composition is a softening composition.

11. The composition according to any one of claims 8 to 10, wherein the composition comprises water.

12. The composition according to claim 11, wherein the water content is greater than 50 wt%, preferably greater than 80 wt%, and more preferably greater than 85 wt%, based on the total weight of the softener composition.

13. The composition according to any one of claims 11, wherein the water content is less than 50 wt%, preferably less than 30 wt%, more preferably less than 10 wt%, and even more preferably less than 5 wt% based on the total weight of the fabric softener, and wherein the concentrated softener composition is suitable for dispersion in water.

14. The use according to any one of claims 1 to 5, or the method according to any one of claims 6 to 7, or the composition according to any one of claims 10 to 12, wherein the water has a hardness value of 0 ppm to 800 ppm CaCO3.

15. The composition according to any one of claims 8 to 14, wherein the composition is stable for at least two months, preferably at least three months, more preferably at least four months, and even more preferably at least six months when stored in a temperature range of 5°C to 40°C, preferably 10°C to 30°C, more preferably 15°C to 25°C.

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