Amino acid group-modified organopolysiloxane and silane, amino acid group-containing compound, and production method thereof

Abstract

An amino acid-modified organopolysiloxane is provided. It has an amino acid derivative bonded to at least one silicon atom of the organopolysiloxane segment constituting the backbone of the organopolysiloxane via an amide bond represented by the following general formula (1): wherein X and Y are independently a C 1-10 divalent hydrocarbon group; m is an integer of 0 to 4; R a is hydrogen atom, a monovalent hydrocarbon group containing 1 to 4 carbon atoms, or an organic group represented by the following general formula (2): (wherein R b is hydrogen atom, a C 1-7 monovalent hydrocarbon group, an alkaline metal, or an alkaline earth metal, and R c is independently hydrogen atom, hydroxy group, or a C 1-10 monovalent hydrocarbon group optionally containing oxygen atom, sulfur atom, or nitrogen atom); and Z is an organic group represented by the general formula (2).

1 . An amino acid group-containing compound represented by the following general formula (11): 
       
         
           
           
               
               
           
         
       
       wherein
 R 20  is a monovalent hydrocarbon group containing 6 to 32 carbon atoms, or a monovalent hydrocarbon group containing 8 to 32 carbon atoms having one hydroxy group, 
 R 21  is hydrogen atom or a monovalent hydrocarbon group containing 1 to 8 carbon atoms, 
 U is sulfur atom, oxygen atom, or an organic group represented by the formula: —NR 24 — wherein R 24  is hydrogen atom, a monovalent hydrocarbon group containing 1 to 6 carbon atoms, or an organic group represented by the following general formula (12): 
 
       
         
           
           
               
               
           
         
       
       (wherein R 22  is hydrogen atom, a monovalent hydrocarbon group containing 1 to 18 carbon atoms, an alkaline metal, or an alkaline earth metal, R 23  is independently hydrogen atom, hydroxy group, or a monovalent hydrocarbon group containing 1 to 10 carbon atoms optionally containing oxygen atom, sulfur atom, or nitrogen atom),
 V is a divalent hydrocarbon group containing 2 to 8 carbon atoms, and 
 W is an organic group represented by the general formula (12), 
 p is 0 or 1, and 
 q is 0 or 1. 
 
     
     
         2 . A method for producing an amino acid group-containing compound of  claim 1  comprising the step of
 reacting an amino group-containing compound represented by the following general formula (13): 
 
       
         
           
           
               
               
           
         
       
       wherein R 20 , V, R 21 , and q are as defined in claim  10 , A is sulfur atom, oxygen atom, or an organic group represented by the formula: —NR 25 — (wherein R 25  is hydrogen atom or a monovalent hydrocarbon group containing 1 to 6 carbon atoms), and p is 0 or 1 with
 a compound represented by the following general formula (14): 
 
       
         
           
           
               
               
           
         
       
       wherein R 22  and R 23  are as defined in claim  10 . 
     
     
         3 . A method according to  claim 2  wherein the compound represented by the general formula (13) is an aliphatic amine containing 6 to 32 carbon atoms. 
     
     
         4 . A method according to  claim 2  wherein the compound represented by the general formula (13) is a higher aliphatic amine containing 12 to 32 carbon atoms. 
     
     
         5 . A method according to  claim 2  wherein the compound represented by the general formula (13) is a hydroxy aliphatic amine containing 6 to 32 carbon atoms. 
     
     
         6 . A method according to  claim 2  wherein the compound represented by the general formula (14) is pyroglutamine acid.