Sulfuric acid amine salt, sulfonic acid amine salt, production thereof and softener composition

Abstract

Provided is a process for preparing a sulfuric acid amine salt (I) represented by the formula (I), which is a neutralization compound between a sulfated compound having a long chain alkyl or alkenyl group and an amine having a long chain alkyl or alkenyl group, useful as softener. wherein R 31 is a linear or branched C 18-36 alkyl or alkenyl group, or a group represented by the formula R 36 -(OA) n -(wherein R 36 is a linear or branched C 12-36 alkyl or alkenyl group, OA is an oxyalkylene group having 2 to 4 carbon atoms and n is a number of from 0.1 to 10 on average), R 32 is a is a linear or branched C 10-36 alkyl or alkenyl group, X is —CONH—, —NHCO—, —COO— or —OCO—, R 33 is a linear or branched C 1-6 alkylene group, R 34 is a linear or branched C 1-6 alkyl or hydroxyalkyl group, or a group represented by R 5 —[B—R 6 ] b —, R 35 is a linear or branched C 1-6 alkyl or hydroxyalkyl group, wherein R 5 is a linear or branched C 10-36 alkyl or alkenyl group, R 6 is a linear or branched C 1-6 alkylene group, B is a group selected from the group consisting of —COO—, —OCO—, —CONH— and —NHCO—, b is a number of 0 or 1 and m is a number of 0 or 1. A sulfonic acid amine salt may be obtained.

1 . A process for preparing a sulfuric acid amine salt (I) represented by the formula (I):  
       
         
           
           
               
               
           
         
       
       wherein in the formulae, R 31  is a linear or branched C 12-36  alkyl or alkenyl group, or a group represented by the formula R 36 -(OA) n —, wherein R 36  is a linear or branched C 12-36  alkyl or alkenyl group, OA is an oxyalkylene group having 2 to 4 carbon atoms and n is a number of from 0.1 to 10 on the average; R 32  is a linear or branched C 10-36  alkyl or alkenyl group; X is —CONH—, —NHCO—, —COO— or —OCO—; R 33  is a linear or branched C 1-6  alkylene group; R 34  is a linear or branched C 1-6  alkyl or hydroxyalkyl group, or a group represented by R 5 —[B—R 6 ] b —, wherein R 5  is a linear or branched C 10-36  alkyl or alkenyl group, R 6  is a linear or branched C 1-6  alkylene group, B is a group selected from the group consisting of —COO—, —OCO—, —CONH— and —NHCO—, b is a number of 0 or 1; R 35  is a linear or branched C 1-6  alkyl or hydroxyalkyl group; and m is a number of 0 or 1, 
 comprising mixing and neutralizing a compound represented by the formula (III) (hereinafter referred to as the compound (III)):  
 R 31 —OSO 2 OH  (III)  
  wherein R 31  indicates the same meaning as in the above description, which has been obtained by sulfating an alcohol (hereinafter referred to as an alcohol (II)) represented by the formula (II):  
 R 31 —OH  (II)  
 wherein R 31  indicates the same meaning as in the above description,  
 with a molten amine (hereinafter referred to as an amine (IV)) represented by the formula (IV):  
                     
 wherein in the formula, R 32 , X, R 33 , R 34 , R 35  and m indicate the respective same meanings as in the above description.  
 
     
     
         2 . The process according to  claim 1 , wherein the added amount of the compound (III) is equal to or less than the amine (IV) in mole.  
     
     
         3 . The process according to  claim 1  or  2 , wherein the compound (III) is added into the amine (IV) mixed into the solvent in advance.  
     
     
         4 . A sulfuric acid amine salt (I) obtained by the process according to  claim 1 .  
     
     
         5 . A sulfuric amine salt (hereinafter referred to as a sulfuric amine salt (I″)) represented by the formula (I″):  
       
         
           
           
               
               
           
         
       
       wherein in the formula, R 41  is a linear or branched C 18-36  alkyl or alkenyl group, or a group represented by the formula R 36 —(OA) n -, wherein R 36  is a linear or branched C 12-36  alkyl or alkenyl group, OA is an oxyalkylene group having 2 to 4 carbon atoms and n is a number of from 0.1 to 10 on average; R 32  is a linear or branched C 10-36  alkyl or alkenyl group; X is —CONH—, —NHCO—, —COO— or —OCO—; R 33  is a linear or branched C 1-6  alkylene group; each of R 44  and R 45  is, independently of the other, a hydrogen atom, a linear or branched C 1-6  alkyl, alkenyl or hydroxyalkyl group, or a group represented by the formula R 32 —X—R 33 —, wherein R 32 , X and R 33  indicate the respective above meanings.  
     
     
         6 . A composition comprising the sulfuric acid amine salt (I) according to  claim 4  or the sulfuric acid amine salt (I″) according to  claim 5  and a solvent.  
     
     
         7 . Use of the sulfuric acid amine salt (I) according to  claim 4  or the sulfuric-acid amine salt (I″) according to  claim 5  as a softener.  
     
     
         8 . A process for preparing a softener composition comprising a step (hereinafter referred to as Step A) of mixing in advance a compound (a) represented by the formula (1) and a compound (b) having one C 12-36 , hydrocarbon group and one group selected from the group consisting of —SO 3 H and —OSO 3 H with each other to obtain a surfactant mixture; and a step (hereinafter referred to as Step B) of dissolving and/or dispersing the thus obtained surfactant mixture in water:  
       
         
           
           
               
               
           
         
       
       wherein in the formula, R 1  is a linear or branched C 10-36  alkyl or alkenyl group; R 2  is a linear or branched C 1-6  alkylene group; A is a group selected from the group consisting of —COO—, —OCO—, —CONH— and —NHCO—, a is a number of 0 or 1, R 3  is a linear or branched C 1-6  alkyl or hydroxyalkyl group or a group represented by R 5 —[B—R 6 ] b — and R 4  is a linear or branched C 1-6  alkyl or hydroxyalkyl group, wherein R 5  is a linear or branched C 10-36  alkyl or alkenyl group, R 6  is a linear or branched C 1-6  alkylene group, B is a group selected from the group consisting of —COO—, —OCO—, —CONH— and —NHCO— and b is a number of 0 or 1.  
     
     
         9 . The process according to  claim 8 , wherein in Step A, an organic solvent is further mixed as the component (c).  
     
     
         10 . The process according to  claim 8  or  9 , wherein in Step A, water is further mixed as the component (d) so that a mass ratio of component (d)/[component (a)+component (b)] is in the range of 0.5/99.5 to 20/80.  
     
     
         11 . A softener composition obtained by the process according to any of  claims 8  to  10 .  
     
     
         12 . Use of the composition obtained by process according to any of  claims 1  to  3  as a softener.  
     
     
         13 . A process for preparing a sulfonic acid amine salt (I′) represented by the formula (I′):  
       
         
           
           
               
               
           
         
       
       wherein R 51  is a linear or branched C 12-36  alkyl or alkenyl group or an C 12-36  alkylaryl group, R 32  is a linear or branched C 10-36  alkyl or alkenyl group; X is —CONH—, —NHCO—, —COO— or —OCO—; R 33  is a linear or branched C 1-6  alkylene group; R 34  is a linear or branched C 1-6  alkyl or hydroxyalkyl group, or a group represented by R 5 —[B—R 6 ] b —, wherein R 5  is a linear or branched C 10-36  alkyl or alkenyl group, R 6  is a linear or branched C 1-6  alkylene group, B is a group selected from the group consisting of —COO—, —OCO—, —CONH— and —NHCO—, b is a number of 0 or 1; R 35  is a linear or branched C 1-6  alkyl or hydroxyalkyl group; and m is a number of 0 or 1, comprising mixing and neutralizing a compound represented by the formula (III′) (hereinafter referred to as the compound (III′)):  
       R 51 —SO 3 H  (III′)  wherein R 51  is defined above, which has been obtained by sulfonating a compound (II′) represented by the formula (II′):    R 51 —H  (II′)    wherein R 51  indicates the same meaning as above,    with a molten amine (hereinafter referred to as an amine (IV)) represented by the formula (IV):                          wherein R 32 , X, R 33 , R 34 , R 35  and m indicate the respective same meanings as in the above description.