Use of special N-alkyl-N-acylglucamines for conditioning hair in hair washing agents

Abstract

The invention relates to N-alkyl-N-acylglucamines of formula (I), which exhibit in hair-washing agents comprising an aqueous surfactant system with at least one anionic surfactant, a hair-conditioning effect, wherein, in formula (I), Ra is a linear or branched, saturated or unsaturated C.sub.5-C.sub.21 alkyl radical and Rb represents a C.sub.1-C.sub.4 alkyl radical, and wherein the N-alkyl-N-acylglucamines (I) contain at least 8 wt. %, based on the total amount of N-alkyl-N-acylglucamines (I), of compounds with a saturated C.sub.16-, C.sub.18- or a mono- or polyunsaturated C.sub.18 fatty acid radical RaCO. ##STR00001##

Claims

1. A method for conditioning hair, comprising the step of contacting the hair with a hairwash composition comprising at least one N-alkyl-N-acylglucamine of the formula (I) and at least one aqueous surfactant system, wherein the at least one aqueous surfactant system comprises at least one alkyl sulfate and/or one alkyl ether sulfate as anionic surfactant, ##STR00006## where in the formula (I) Ra is a linear saturated C.sub.5-C.sub.21 alkyl radical, a branched saturated C.sub.5-C.sub.21 alkyl radical, a linear unsaturated C.sub.5-C.sub.21 alkyl radical, or a branched unsaturated C.sub.5-C.sub.21 alkyl radical and Rb is a C.sub.1-C.sub.4 alkyl radical, and wherein the at least one N-alkyl-N-acylglucamine according to formula (I) comprises at least 8 wt %, based on the total amount of the at least one N-alkyl-N-acylglucamine, of a saturated C.sub.16, C.sub.18, or singly or multiply unsaturated C.sub.18 fatty acid radical RaCO.

2. The method as claimed in claim 1, wherein Rb is a methyl radical.

3. The method as claimed in claim 1, wherein the radical Ra is derived from lauric acid, palmitic acid, stearic acid, oleic acid, linoleic acid, or linolenic acid.

4. The method as claimed in claim 1, wherein the at least one N-alkyl-N-acylglucamine according to formula (I) comprises at least 8 wt % of an unsaturated C.sub.18 fatty acid radical.

5. The method as claimed in claim 1, wherein the at least one N-alkyl-N-acylglucamine according to formula (I) comprises at least 8 wt % of an unsaturated C.sub.18 fatty acid radical and at least 30 wt % of a saturated C.sub.12 fatty acid radical.

6. The method as claimed in claim 1, wherein the aqueous surfactant system comprises an alkyl sulfate and/or an alkyl ether sulfate as anionic surfactant and a betaine surfactant.

7. The method as claimed in claim 1, wherein the aqueous surfactant system comprises a linear C.sub.8-C.sub.20 alkyl sulfate and/or a linear C.sub.8-C.sub.20 alkyl ether sulfate.

8. The method as claimed in claim 7, wherein the aqueous surfactant system comprises lauryl sulfate and/or a lauryl ether sulfate.

9. The method as claimed in claim 1, wherein the aqueous surfactant system comprises an acylamidopropylbetaine or an alkylbetaine.

10. The method as claimed in claim 1, for improving the ease of hair combing.

11. A hairwash composition comprising (a) at least one N-methyl-N-acylglucamine of the formula (I) containing at least 8 wt %, based on the total amount of N-alkyl-N-acylglucamine, of a saturated C.sub.16, C.sub.18, or singly or multiply unsaturated C.sub.18 fatty acid radical RaCO, as component (A), ##STR00007## where in the formula (I) Ra is a linear saturated C.sub.5-C.sub.21 alkyl radical, a branched saturated C.sub.5-C.sub.21 alkyl radical, a linear unsaturated C.sub.5-C.sub.21 alkyl radical, or a branched unsaturated C.sub.5-C.sub.21 alkyl radical and Rb is a C.sub.1-C.sub.4 alkyl radical, (b) at least one anionic surfactant selected from the group consisting of the alkyl ether sulfates and alkyl sulfates, as component (B), (c) optionally betaine surfactants as component (C), (d) optionally further surfactants as component (D), (e) refatting agents as component (E), (f) water as component (F), and (g) optionally further additives, such as preservatives, fragrances, and dyes, as component (G).

12. The hairwash composition as claimed in claim 11, with the proviso that the hairwash composition contains no cationic polymers.

13. The hairwash composition as claimed in claim 11 in the form of a greasy hair, dry hair, stressed hair, or dandruff-affected hair hairwash composition, or of a color shampoo, baby shampoo, or sports shampoo.

14. The hairwash composition as claimed in claim 11, wherein Rb is a methyl radical.

15. The hairwash composition as claimed in claim 11, wherein the radical Ra is derived from lauric acid, palmitic acid, stearic acid, oleic acid, linoleic acid, or linolenic acid.

16. The hairwash composition as claimed in claim 11, wherein the at least one N-alkyl-N-acylglucamine according to formula (I) comprises at least 8 wt % of an unsaturated C.sub.18 fatty acid radical.

17. The hairwash composition as claimed in claim 11, wherein the at least one N-alkyl-N-acylglucamine according to formula (I) comprises at least 8 wt % of an unsaturated C.sub.18 fatty acid radical and at least 30 wt % of a saturated C.sub.12 fatty acid radical.

Description

EXAMPLES

(1) The N-methyl-N-acylglucamines described in table 1 were prepared according to EP 0 550 637 from the corresponding fatty acid methyl esters and N-methylglucamine in the presence of 1,2-propylene glycol as solvent, and were obtained in solid form comprising active substance and 1,2-propylene glycol (all figures in wt %).

(2) TABLE-US-00001 TABLE 1 Preparation examples for N-methyl-N-acylglucamines 1,2- Prep- Active Propylene Melting aration Methyl substance glycol point example ester Triglyceride (%) (%) ( C.) 1 C12/14 90 10 85 (C12: 70%, C14 30%) 2 Coconut oil 90 10 50 (C8: 6%; C10: 6%; C12: 48% C14: 20% C16: 10%; C18: 2%, C18 = 8%) 3 C16/18 80 20 65 (C16: 60%; C18: 40%) 4 C12/18 90 10 70 unsaturated (C12; 60%, C14: 26%, C16: 4% C18: 1% C18 (oleic acid): 8% C18 = 1% 5 C16/18 80 20 45 unsaturated C16: 32% C18: 8% C18 = 52% C18 = 8%

(3) Aqueous surfactant systems comprising sodium lauryl ether sulfate (SLES) [degree of ethoxylation 2 EO] (Genapol LRO Liq., Clariant), cocoamidopropylbetaine (Genagen CAB 818, Clariant), and sugar surfactants, in the mass ratios according to the table below, were produced and adapted to a uniform viscosity of 5000 mPas by addition of sodium chloride. The pH was adjusted to 5.5. The total surfactant content in each case was 15%.

(4) The resulting surfactant systems were subjected to sensory evaluation in hairwash tests (=poor; o=moderate; +=good).

(5) TABLE-US-00002 TABLE 2 Examples of inventive uses/hairwash compositions Hair Ease of sensation, hair Example Composition Ratio dry combing Comparative SLES/betaines 7:3 example 1 dried out Comparative SLES/betaine/preparation 6:3:1 example 2 example 1 dried out Inventive SLES/betaine/preparation 6:3:1 + + example 1 example 2 refatting Inventive SLES/betaine/preparation 6:3:1 + + example 2 example 4 refatting Inventive SLES/betaine/preparation 6:3:1 + + example 3 example 3 refatting Comparative SLES/betaine/coco- 6:3:1 example 3 glucosides dried out

(6) As is apparent from inventive examples 1-3 and comparative examples 1-3, the glucamides from example 1-3, in contrast to the base system (comparative example 1) and to a glucamide with C12/14 chain fraction (comparative example 2), impart positive sensory effects to the hair and lead to improved ease of combing. Comparable sugar surfactants (comparative example 3) likewise do not have this effect.

FORMULATION EXAMPLES

Formulation Example 1

(7) TABLE-US-00003 Care shampoo Sodium laureth sulfate (2 EO) .sup.8% Cocoamidopropylbetaine .sup.3% N-Alkyl-N-acylglucamine as per preparation example 2 .sup.2% Cocoamide MEA 0.5% Sodium chloride 0.5% Fragrance 0.5% Preservative q.s. Water ad 100%.sup.

Formulation Example 2

(8) TABLE-US-00004 Care shampoo Sodium laureth sulfate (2 EO) .sup.8% Cocoamidopropylbetaine .sup.3% N-Alkyl-N-acylglucamine as per preparation example 4 .sup.2% Cocoamide MEA 0.5% Sodium chloride 0.5% Fragrance 0.5% Polyquaternium-10 0.2% Preservative q.s. Water ad 100%.sup.

(9) The stated percentages correspond to weight % and are based on the amount of active component.

Use Example

(10) An inventive shampoo formulation B was assessed for fragrance stabilization. This was done by preparing the formulation, adding fragrance, storing it in closed glass bottles for two weeks at 40 C., and then having a panel of three trained assessors evaluate the remaining fragrance intensity in comparison to a comparative formulation A stored at 25 C.

(11) TABLE-US-00005 Comparative formulation A Formulation B Composition Composition Formulation (wt %) (wt %) Sodium lauryl ether 9 7.3 sulfate Cocoamidopropylbetaine 3 2.75 Glucamide as per 0 0.92 preparation example 4 PEG-40 hydr. castor oil 0.2 0 PEG-200 glyceryl 0.5 0 palmate PEG-7 glyceryl cocoate 0.5 0 Sodium benzoate 0.2 0.2 Sodium salicylate 0.2 0.2 Polyquaternium-7 0.2 0.2 Waterlilly fragrance 0.5 0.5 Glycerol 0.8 0.8 Water ad 100 ad 100 Evaluation of the odor Significantly reduced Fragrance intensity after two weeks' storage fragrance intensity, largely unchanged time at 40 C. head note degraded

(12) The result of the experiment shows that formulation B, containing no ethoxylates with terminal OH groups such as PEG-40 hydr. castor oil, PEG-200 glyceryl palmate, or PEG-7 glyceryl cocoate, but instead having a glucamide, exhibits a much better fragrance stability on hot storage. It can therefore be concluded that the use of glucamides rather than of ethoxylates having terminal OH groups, as a hair-conditioning component, solubilizer, or thickener, leads at the same time to an improvement in the fragrance stability.