New (pseudo)ceramide compounds useful in the field of hair care, like shampoos, after-shampoos, lotions or hair balms

摘要

#CMT# #/CMT# (Pseudo)ceramide compounds (I), are new. #CMT# : #/CMT# (Pseudo)ceramide compounds of formula R1-C(=O)-N(X)-(CH(R2)) m-CH(R3)-(CH 2) n-O-C(=O)-(CH 2) p-N +>R4R5R6 (I), are new. X : H or 1-4C carbon chain, preferably H; R1, R : 4-25C carbon chain (optionally containing 1-2 OH groups); R2 : H, 1-4C alkyl or OH, preferably H; R3 : -R, -O-C(=O)-R or -CH 2-O-C(=O)-R; R4-R6 : optionally unsaturated 1-12C alkyl or aromatic, preferably methyl, ethyl, propyl, butyl or lauryl; Z : halo, preferably Br or Cl; m, n : 0-3, preferably 0-1; and p : 1-3. Independent claims are included for: (1) the preparation of (I); and (2) cosmetic composition comprising (I) in combination/mixture with inert excipients or vehicle. #CMT#USE : #/CMT# (I) is useful in the field of hair care, like shampoos, after-shampoo, lotions or hair balms (claimed). #CMT#ORGANIC CHEMISTRY : #/CMT# Preparation (Claimed): Preparation of (I) comprises: coupling of an alcohol compound of formula R1-C(=O)-N(X)-(CH(R2)) m-CH(R3)-(CH 2) n-OH (II) and a halo compound of formula Y1-C(=O)-(CH 2) p-Z (III) in a non-halogenated inert solvent to obtain a haloester; and reacting the obtained haloester with tert-amine of formula NR4R5R6 to form quaternary ammonium salt (I). Y1, Z : Cl or Br. Preferred Process: The coupling of (II) and (III) is done at room temperature. The coupling of the haloester with tert-amine is done in a solvent comprising ethyl acetate and acetone. Preferred Components: The non-halogenated inert solvent is ethyl acetate. (I) is present at 0.001-20 wt.% in the composition. #CMT#EXAMPLE : #/CMT# An ester compound of formula C 5H 11-CH=CH-CH 2-CH=CH-(CH 2) 7-C(=O)-NH-CH 2-C(OH)-CH 2-O-C(=O)-C 15H 31(1 g) was dissolved in ethyl acetate (4 ml). Then chloroacetyl chloride (1.2 equivalents) was added at room temperature and the reaction mixture was agitated for 24 hours. The reaction mixture was then washed with an aqueous solution of sodium bicarbonate (2x 5 ml) and water (2x 5 ml). Then the obtained organic phase was then used directly to the next step. The triethylamine (4 equivalents) was added drop by drop to the reaction mixture for 20 minutes. Then the reaction mixture was agitated at 50[deg] C for 48 hours. After cooling, the reaction mixture was concentrated to form a triethyl-ammonium salt of formula C 5H 11-CH=CH-CH 2-CH=CH-(CH 2) 7-C(=O)-NH-CH 2-CH(CH 2-O-C(=O)-C 15H 31)(O-C(=O)-CH 2-N +>-(CH 2-CH 3) 3)Cl ->(60%).