Hair cosmetic, aminocarboxylic acid amide and method for producing the same

Abstract

A hair cosmetic which can impart, to hairs, flexibility, smoothness and oily feeling when the hairs are wetted and smoothness, softness and combing easiness after the hairs are dried are provided, the hair cosmetic comprising an amine represented by the formula (I): Formula (I) (wherein R 1 represents a C 8-40 alkyl group or alkenyl group or a group represented by the formula R 5 O—(AO) n —C m H 2m — (R 5 represents a C 8-40 alkyl group or alkenyl group having 8 to 40 carbon atoms, A represents a C 2-3 alkylene group, n denotes a number from 0 to 30 in average and m denotes an integer of 2 or 3), R 2 represents a C 1-5 alkylene group, R 3 represents H, a C 1-24 alkyl group, alkenyl group or hydroxyalkyl group or a C 6-28 aryl group or arylalkyl group, R 4 represents H, a C 1-5 alkyl group, alkylene group or hydroxyalkyl group or a C 6-28 aryl group or arylalkyl group, p denotes an integer from 1 to 3, q and r denote integers from 0 to 2 and p+q+r is equal to 3. Also, the amine (I) can be produced with high selectivity and highly economically by reacting a primary amine with an aminocarboxylic acid to run amidation. An amine represented by the formula (1), its salt or quaternary ammonium salt are also provided: Formula (1)

1 . A hair cosmetic comprising an amine compound (hereinafter referred to as amine (I)) represented by the formula (I):  
       
         
           
           
               
               
           
         
       
       (wherein R 1  represents a straight-chain or branched alkyl or alkenyl group having 8 to 40 carbon atoms or a group represented by the formula R 5 O—(AO) n —C m H 2m — (R 5  represents a straight-chain or branched alkyl or alkenyl group having 8 to 40 carbon atoms, A represents an alkylene group having 2 to 3 carbon atoms, n denotes a number from 0 to 30 on the average and m denotes an integer of 2 or 3, where nA's may be the same as or different from one another), R 2  represents a straight-chain or branched alkylene group having 1 to 5 carbon atoms, R 3  represents a hydrogen atom, a straight-chain or branched alkyl, alkenyl or hydroxyalkyl group having 1 to 24 carbon atoms or an aryl or arylalkyl group having 6 to 28 carbon atoms, R 4  represents a hydrogen atom, a straight-chain or branched alkyl, alkylene or hydroxyalkyl group having 1 to 5 carbon atoms or an aryl or arylalkyl group having 6 to 28 carbon atoms, R 3  and R 4  may form a ring either independently or in combination, p denotes an integer from 1 to 3, q and r denote an integer from 0 to 2 and p+q+r is equal to 3, that pR 1′ s, pR 2′ s, qR 3′ s and rR 4′ s may be the same as or different from one another.).  
     
     
         2 . The hair cosmetic according to  claim 1 , wherein in the formula (I), R 1  represents a straight-chain or branched alkyl or alkenyl group having 12 to 24 carbon atoms or a group represented by the formula R 5 O—(AO) n —C m H 2m — (R 5  represents a straight-chain or branched alkyl or alkenyl group having 12 to 24 carbon atoms, A, n and m represent the same meaning as above, R 2  represents a straight-chain alkylene group having 1 to 3 carbon atoms, R 3  and R 4  represent a straight-chain or branched alkyl or hydroxyalkyl group having 1 to 3 carbon atoms or an aryl or arylalkyl group having 6 to 28 carbon atoms (R 3  and R 4  may form a ring either independently or in combination), p is 1 or 2 and q and r are 0 or 1.  
     
     
         3 . A hair cosmetic composition comprising the amine compound (I) as claimed in  claim 1  and at least one acid selected from the group consisting of inorganic acids and organic acids.  
     
     
         4 . A hair cosmetic composition comprising the amine compound (I) as claimed in  claim 1  and an alcohol having 10 to 30 carbon atoms.  
     
     
         5 . A hair cosmetic composition comprising the amine compound (I) as claimed in  claim 1 , at least one acid selected from the group consisting of inorganic acids and organic acids and an alcohol having 10 to 30 carbon atoms, wherein the content of the amine compound (I) is 0.1 to 15% by weight, the content of the acid is 0.3 to 10 mol equivalents to the amine (I) and the content of alcohol having 10 to 30 carbon atoms is 0.5 to 15% by weight.  
     
     
         6 . A method of producing the amine compound (I) as claimed in  claim 1 , comprising reacting a primary amine represented by the formula (II) with an aminocarboxylic acid represented by the formula (III) to run amidation:  
       
         
           
           
               
               
           
         
       
       (wherein R 1 , R 2 , R 3 , R 4 , p, q and r are the same as those of claim  1 .).  
     
     
         7 . The method according to  claim 6 , wherein R 1  represents a straight-chain or branched alkyl or alkenyl group having 12 to 24 carbon atoms or a group represented by the formula R 5 O—(AO) n —C m H 2m — (R 5  represents a straight-chain or branched alkyl or alkenyl group having 12 to 24 carbon atoms, A, n and m have the same meaning as above, R 2  represents a straight-chain alkylene group having 1 to 3 carbon atoms, R 3  and R 4  represent a straight-chain or branched alkyl or hydroxyalkyl group having 1 to 3 carbon atoms or an aryl or an arylalkyl group having 6 to 10 carbon atoms (R 3  and R 4  may form a ring either independently or in combination), p is 1 or 2 and q and r are 0 or 1.  
     
     
         8 . The method according to  claim 6 , wherein an aminocarboxylic acid represented by the formula (III) is used in an amount of 0.5 to 3 equivalents to one equivalent of the primary amine represented by the formula (II) to run an amidation reaction at 120 to 250° C.  
     
     
         9 . The method according to  claim 6 , wherein the aminocarboxylic acid represented by the formula (III) is obtained by adding an acid to an alkali metal salt of the aminocarboxylic acid.  
     
     
         10 . The method according to  claim 6 , wherein washing with water and solid-liquid separation are carried out after the amidation.  
     
     
         11 . An amine represented by the formula (1), an acid salt thereof or a quaternary ammonium salt thereof:  
       
         
           
           
               
               
           
         
       
       (wherein R 1  represents a straight-chain or branched alkyl or alkenyl group having 8 to 40 carbon atoms, A represents an alkylene group having 2 to 3 carbon atoms, n denotes a number from 0 to 30 on the average and m denotes an integer of 2 or 3, R represents a straight-chain orbranched alkylene group having 1 to 5 carbon atoms, R 3  and R 4 , which are the same as or different from each other, represent a hydrogen atom, a straight-chain or branched alkyl, alkenyl or hydroxyalkyl group having 1 to 5 carbon atoms or an aryl or arylalkyl group having 6 to 28 carbon atoms, R 3  and R 4  may form a ring either independently or in combination, p denotes an integer from 1 to 3, q and r denote an integer from 0 to 2 and p+q+r is equal to 3, provided that (n×p)A's, pR 1′ s, pn′s, pm′s, pR 2′ s, qR 3′ s and rR 4′ s may be the same as or different from one another.).  
     
     
         12 . The quaternary ammonium salt according to  claim 11 , which is a compound represented by the formula (2):  
       Formula (2)  
       
         
           
           
               
               
           
         
       
       (wherein R 1 , A, n, m, R 2 , R 3 , R 4 , p, q and r are the same as above, R 5  represents a straight-chain or branched alkyl or hydroxyalkyl group having 1 to 5 carbon atoms and X represents an anionic ion group.).  
     
     
         13 . The amine, the acid salt or the quaternary ammonium salt according to  claim 11 , wherein R 1  represents a straight-chain or branched alkyl or alkenyl group having 10 to 28 carbon atoms, R 2  represents a straight-chain or branched alkylene group having 1 to 3 carbon atoms and p denotes an integer from 1 or 2.  
     
     
         14 . A surfactant comprising the amine, the salt or the quaternary ammonium salt as claimed in  claim 11 .  
     
     
         15 . Use of the amine compound (I) as defined in  claim 1  for cosmetic material.