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KR-20260064721-A - Uses of cationic surfactant mixtures for dispersing quaternary ester ammonium components in water

KR20260064721AKR 20260064721 AKR20260064721 AKR 20260064721AKR-20260064721-A

Abstract

The present invention provides a use of a cationic surfactant mixture for dispersing a quaternary ester ammonium component comprising one or more compounds of formula (IV) in water, wherein the cationic surfactant mixture can be obtained by a method comprising: (b) an esterification step of a hydroxyl group-containing compound or a mixture of hydroxyl group-containing compounds using a mixture of compounds containing one or more carboxyl groups, and (b) a cation formation step from the reaction product of step I. The present invention also provides the composition and use thereof. Advantageously, the dispersion of the present invention is highly stable. The quaternary ester ammonium component comprises one or more compounds of formula (IV).

Inventors

  • 피 볼레다 베르나트
  • 소브레비아스 알라바우 자우메
  • 노구에스 로페즈 블란카
  • 문도 블란치 미??

Assignees

  • 카오 코포레이션 에스.에이.유.

Dates

Publication Date
20260507
Application Date
20240904
Priority Date
20230905

Claims (15)

  1. Use of a cationic surfactant mixture obtainable by a method comprising the following steps for dispersing at least one quaternary ester ammonium component in water: Step I: Esterification of a) using b); and Step II: Formation of cations from the reaction products of Step I: a) is a hydroxyl group-containing compound or a mixture of hydroxyl group-containing compounds comprising a.1 and optionally a.2, and: - a.1 is an alkanolamine of formula (I) or a mixture of alkanolamines: In the chemical formula, R1 is hydrogen, a C1-C6 alkyl group, and a residue Selected from, R2 is a C1-C6 alkylene group, R3 is hydrogen or methyl, and n is 0 or an integer from 1 to 20; - a.2 is a polyol, which is optionally alkoxylated and has a MW in the range of 60 to 190 g/mol; b) is a mixture of compounds containing one or more carboxyl groups, including b.1 and b.2: - b.1 is a monocarboxylic acid of formula (II) or a mixture of monocarboxylic acids: In the formula, R6 is a linear or branched C6-C23 alkyl group or alkenyl group; or its alkyl ester or glyceride, preferably a linear or branched C6-C23 alkyl or alkenyl ester; - b.2 is a dicarboxylic acid of formula (III) or a mixture of dicarboxylic acids, or reactive derivative(s) thereof, and: In the chemical formula, L is a saturated or unsaturated, linear or branched group having 1 to 10 carbon atoms, or a cyclic group having 3 to 10 carbon atoms, each of which is optionally substituted by a C1 - C6 saturated or unsaturated group; preferably represented as (CH(R11)) m or ( C6 - C10 arylene) optionally substituted by one or more R11s, each R11 being independently hydrogen, OH, or a C1-C6 saturated or unsaturated group, m is 0 or an integer from 1 to 10, and if m≥2, the chain (CH)m optionally contains one or more double bonds and/or cyclic group(s); a.1), a.2), b.1), and b.2) are introduced into the reaction system of Step I in amounts resulting in the following molar ratios: - The molar ratio of one-dimensional/two-dimensional(dimensional)(b.1/b.2) is 0.3 to 5.0; - The equivalence ratio of organic carboxyl groups and organic hydroxyl groups (COOH/OH) present in the system is 0.4 to 0.8; - The molar ratio between the compound(s) under Definition a.2 and the compound(s) under Definition a.1 is 0 to 0.5, and The quaternary ester ammonium component comprises one or more compounds of formula (IV): In the chemical formula, X1 represents a hydroxyalkyl group containing 1 to 4 carbon atoms or an alkyl group containing 1 to 4 carbon atoms; R7 is a linear or branched C6-C23 alkyl group or an alkenyl group; R8 and R9 each independently represent -H, -OH, or -O-Tq-C(O)-R7; T represents a -(OCH2CH2)a-(OCHR4CH2)b- group, 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 is 0 to 26; preferably 0 to 6, most preferably an average degree of alkoxylation corresponding to 0; q represents the average number within the range of 0 to 26; m, r, and p each independently represent an average number within the range of 1 to 4, and A represents an anion, preferably a halide, phosphate, or alkyl sulfate, use.
  2. In paragraph 1, The amounts of compounds a.1, a.2, b.1, and b.2 are - The molar ratio of monocal(s)/discal(s)(b.1/b.2) is 0.6 to 4.0, preferably 1.5 to 4.0; - The equivalence ratio between organic carboxyl groups and organic hydroxyl groups (COOH/OH) present in the system is 0.5 to 0.7; - Compound(s) under Definition a.2 and compound(s) under Definition a.1, such that the molar ratio between them is 0, Introduced into the reaction system of Step I in an amount resulting in a molar ratio, use.
  3. In paragraph 1 or 2, One or more compounds of chemical formula (IV) - m, r, and p are equal to 2 and/or; - q is 0 and/or; - R7 is a linear or branched alkyl group or alkenyl group containing 6 to 23 carbon atoms and 0 to 3 double bonds, use.
  4. In any one of paragraphs 1 through 3, For dispersing in water a quaternary ester ammonium compound comprising at least one quaternary mono-ester ammonium compound of formula (IV.1), at least one quaternary di-ester ammonium compound of formula (IV.2), and at least one quaternary tri-ester ammonium compound of formula (IV.3): In the chemical formula, 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 one of paragraphs 1 to 3, use.
  5. In any one of paragraphs 1 through 4, Uses in which the weight ratio between the mixture of the cationic surfactant and the quaternary ester ammonium component is 10:90 to 70:30, preferably 20:80 to 60:40, more preferably 30:70 to 50:50.
  6. (i) mixing one or more compounds of formula (IV) with a cationic mixture as defined in any one of claims 1 to 5, (ii) the step of adding water, and (iii) Stirring step A method for dispersing a quaternary ester ammonium component in water, comprising one or more compounds of the formula (IV) as defined in any one of claims 1 to 5.
  7. In paragraph 6, It further includes a step of adding flavoring; In particular, flavorings are added before water is added, method.
  8. A composition comprising a cationic mixture and a quaternary ester ammonium component as defined in any one of claims 1 to 5.
  9. In paragraph 8, A composition further comprising a flavoring.
  10. In Article 8 or 9, A composition that is a softening agent composition.
  11. In any one of paragraphs 8 through 10, A composition containing water.
  12. In Paragraph 11, A composition having a water content of more than 50% by weight, preferably more than 80% by weight, and more preferably more than 85% by weight, based on the total weight of the softener composition.
  13. In Paragraph 11, The water content is less than 50 weight%, preferably less than 30 weight%, more preferably less than 10 weight%, and even more preferably less than 5 weight% based on the total weight of the fabric softener, and The concentrated softener composition is suitable for dispersion in water, Composition.
  14. In any one of paragraphs 1 through 5, any one of paragraphs 6 through 7, or any one of paragraphs 10 through 12, A use, method, or composition having a hardness value of CaCO₃ of 0 to 800 ppm, water.
  15. In any one of paragraphs 8 through 14, A composition that is stable when stored at a temperature of 5°C to 40°C, preferably 10°C to 30°C, more preferably 15°C to 25°C for at least 2 months, preferably at least 3 months, more preferably at least 4 months, and even more preferably at least 6 months.

Description

Uses of cationic surfactant mixtures for dispersing quaternary ester ammonium components in water The present invention relates to the use of a cationic surfactant mixture for dispersing a quaternary ester ammonium compound in water, which is useful for manufacturing a fabric softener composition. Quaternary ester ammonium compounds, generally referred to as "esterquats (EQ)," have been found to have a wide range of uses as fabric softener active ingredients due to their high softening performance (e.g., softening of textile fibers and fabrics, as well as keratin fibers such as hair), biodegradability, relatively low aquatic toxicity, and excellent cosmetic suitability. Softener formulations containing ester quarts require specific manufacturing procedures (including stirring and temperature conditions) to ensure the stability of the aqueous dispersion and avoid phase separation. There is still demand for softener active ingredient formulations that exhibit a transparent viscous liquid that can be directly and easily dispersed in water, including tap water, at temperatures between 5°C and 40°C in combination with fragrances, and that such formulations are homogeneous and stable during storage. Another requirement for fabric softener formulations is the reduction of their environmental footprint from manufacturing to their use as a softener ingredient, thereby yielding more sustainable products that can contribute to various beneficial effects such as reduced water, reduced plastic, reduced energy, and/or the ecological acceptability of the product and its use. The possibility of dispersing the softener in water at low temperatures, namely between 5°C and 40°C, not only enables a reduction in the need for resources to treat water (for softener manufacturers), but also may allow end consumers to directly manufacture fabric softeners from concentrated softeners by dispersing the fabric softener directly into readily available tap water at home. WO2016096614A1 describes a textile treatment agent containing a specific ester quart. Fabric softener formulations with high storage stability are provided only in the additional presence of cationic thickeners and nonionic emulsifiers. EP1136471A1 describes a cationic surfactant obtained from alkanolamines, dicarboxylic acids, and fatty alcohols. This patent describes that such cationic surfactants demonstrate efficacy in softening and conditioning natural and synthetic fibers. Considering the above, the present invention aims to solve the problem of providing a homogeneous and stable ester quart dispersion that is not sensitive to water hardness and can be easily prepared at room temperature. The inventors have discovered that when an ester quart is previously mixed with a mixture of cationic surfactants of specific properties, a stable aqueous dispersion of the ester quart of interest is achieved. Accordingly, the present invention provides a use for a cationic surfactant mixture obtainable by a method comprising the following steps for dispersing at least one quaternary ester ammonium component in water: Step I: Esterification of a) using b); and Step II: Formation of cations from the reaction products of Step I: a) is a hydroxyl group-containing compound or a mixture of hydroxyl group-containing compounds comprising a.1 and optionally a.2, and: - a.1 is an alkanolamine of formula (I) or a mixture of alkanolamines and: In the chemical formula, R1 is hydrogen, a C1-C6 alkyl group, and a residue Selected from, R2 is a C1-C6 alkylene group, R3 is hydrogen or methyl, and n is 0 or an integer from 1 to 20; - a.2 is a polyol, which is optionally alkoxylated and has a MW in the range of 60 to 190 g/mol; b) is a mixture of compounds containing one or more carboxyl groups, including b.1 and b.2: - b.1 is a monocarboxylic acid of formula (II) or a mixture of monocarboxylic acids and: In the chemical formula, R6 is a linear or branched C6-C23 alkyl group or alkenyl group; or its alkyl ester or glyceride, preferably a linear or branched C6-C23 alkyl or alkenyl ester; - b.2 is a dicarboxylic acid of formula (III) or a mixture of dicarboxylic acids, or reactive derivative(s) thereof, and: In the chemical formula, L is a saturated or unsaturated, linear or branched group having 1 to 10 carbon atoms, or a cyclic group having 3 to 10 carbon atoms, each of which is optionally substituted by a C1 - C6 saturated or unsaturated group; preferably represented as (CH(R11)) m or ( C6 - C10 arylene) optionally substituted by one or more R11s, each R11 being independently hydrogen, OH, or a C1-C6 saturated or unsaturated group, m is 0 or an integer from 1 to 10, and if m≥2, the chain (CH)m optionally contains one or more double bonds and/or cyclic group(s); a.1), a.2), b.1), and b.2) are introduced into the reaction system of Step I in amounts resulting in the following molar ratios: - The molar ratio of monocal(s)/discal(s)(b.1/b.2) is 0.3 to 5.0; preferably - The equivalence ratio of organi