Process for producing epoxyorganosilicon compounds

Abstract

The present invention describes a method for producing epoxyorganosilicon compounds through the platinum-catalyzed hydrosilation reaction of ethylenically unsaturated epoxides and a silicon-hydride in the presence of a carboxylic acid salt. Also taught herein is the use of carboxylic acid salts in compositions of epoxyorganosilicon compounds to provide compositions of greater stability.

What is claimed is:  
     
         1 . An epoxysilicon composition comprising an epoxy organosilicon and a salt of a carboxylic acid, wherein said epoxysilicon composition exhibits reduced tendency to gel on storage at room temperature compared to a composition containing the same ingredients as said epoxysilicon composition except the carboxylic acid salt.  
     
     
         2 . A composition as in  claim 1  wherein the epoxy organosilicon is selected from the group consisting of an epoxy silane and an epoxy silicone.  
     
     
         3 . A composition as in  claim 1  wherein the epoxy silane is an epoxy alkoxy silane.  
     
     
         4 . The composition according to  claim 1  wherein the salt is of the formula R 6 CO 2 M wherein M is selected from the group consisting of an alkali, alkaline earth, transition metal, and an ammonium ion and R 6  represents a monovalent hydrocarbon group having one to 50 carbon atoms, optionally substituted with amino, hydroxyl, carboxyl or ester groups.  
     
     
         5 . The composition of  claim 4  wherein R 6  is a linear or branched alkyl of one to ten carbon atoms.  
     
     
         6 . The composition as in  claim 4  wherein the carboxylic acid salt is ammonium or sodium propionate.  
     
     
         7 . A process comprising reacting: 
 a) an ethylenically unsaturated epoxide of the formula:                          where R is a single bond or an alkylene optionally containing alkyl pendant groups; R 1  is a hydrogen, alkyl, straight, branched, or cyclic; R 2  and R 3  are individually hydrogen, straight, branched or cyclic alkyl, or any two of R 1 , R 2  and R 3 , taken together are alkylene and combined with the carbon atom or atoms to which they are attached form a 5 to 12 carbon cyclic ring, optionally containing alkyl pendants; and the number of carbon atoms in R, R 1 , R 2 , and R 3  are such that the total number of carbon atoms in the epoxide is from 4 to 50, with    b) an organosilicon hydride selected from the group consisting of hydridosilane and hydrido organosiloxane, in the presence of    c) a catalytically effective amount of platinum catalyst and    d) a member selected from the group consisting of carboxylic acid salt, hydroxy acid, amino acid and polymeric acid,    wherein said process exhibits reduced tendency to undergo unwanted side-reactions selected from the group consisting of epoxide ring-opening polymerization and olefin isomerization compared to a process comprising steps a), b) and c) but not step d).    
     
     
         8 . The process of  claim 7  wherein the hydridosilane is an alkoxysilane with the general formula R 4   n (OR 4 ) 3−m SiH, wherein R 4  is a branched or linear alkyl group of 1 to 18 carbon atoms, a cyclic alkyl group of four to eight carbon atoms or an aryl, alkaryl, or aralkyl group of six to twelve carbon atoms, optionally containing halogen, oxygen, or nitrogen substituents with the proviso that such substituents do not interfere with either hydrosilation or promotion, and n is an integer selected from 0, 1, and 2.  
     
     
         9 . The process of  claim 8  wherein the alkoxysilane is trimethoxysilane, triethoxysilane, methyldimethoxysilane or methyldiethoxysilane.  
     
     
         10 . The process of  claim 7  wherein the hydrido organosiloxane possesses the general formula [R a (H) b SiO (4−a−b)/2 ] n  wherein R represents a monovalent hydrocarbon radical, a has a value of from 1 to 2.99, b has a value of from 0.001 to 1, and the sum of a+b has a value of from 1.5 to 3.0 and n=2 to 400.  
     
     
         11 . The process of  claim 7  wherein the hydrido organosiloxane is MD x D′ y M, where x=0 to 200, y=1 to 200, M=—O ½ Si(CH 3 ) 3 , D′=—OSi(H)(CH 3 )—, and D=—OSi(CH 3 ) 2 —.  
     
     
         12 . The process in  claim 7  wherein the ethylenically unsaturated epoxide is 4-vinylcyclohexene monoxide or butadiene monoxide.  
     
     
         13 . The process in  claim 7  wherein the carboxylic acid salt is represented by the formula R 6 CO 2 M wherein M is selected from the group consisting of an alkali, alkaline earth, transition metal, and an ammonium ion and R 6  represents a monovalent hydrocarbon of one to 50 carbon atoms, optionally substituted with amino, hydroxyl, carboxyl or ester groups.  
     
     
         14 . The process in  claim 13  wherein R 6  is a linear or branched alkyl of one to ten carbon atoms.  
     
     
         15 . The process in  claim 13  wherein the carboxylic acid salt is ammonium or sodium propionate.  
     
     
         16 . The process as in  claim 7  wherein the carboxylic acid salt is selected from the group consisting of lithium acetate, sodium acetate, potassium acetate, potassium benzoate, sodium trifluoroacetate, sodium propionate, calcium acetate, samarium (III) acetate, copper (II) acetate, copper (II) ethylhexanoate, indium (III) acetate, ammonium formate, ammonium acetate, ammonium isovalerate, ammonium 2ethylbutyrate, ammonium propionate, ammonium chloride and combinations thereof.  
     
     
         17 . The process in  claim 7  wherein the platinum catalyst is a solution of chloroplatinic acid.