Glycerol ester-free functionalized vegetable oil derivatives and their latex compositions

Abstract

The present invention is directed to a fatty amide (meth)acrylate monomer, methods of making the monomer, and latex polymers comprising the fatty amide (meth)acrylate monomer. The monomers are derived by reacting unsaturated vegetable oils with ethanolamine or substituted ethanolamine. The vegetable oil derivative is then reacted with either (meth)acryloyl chloride or (meth)acrylic acid to form a fatty amide (meth)acrylate monomer or the product of the reaction of hydroxyethyl(meth)acrylate reacted with isophorone diisocyanate to form a urethane fatty amide(meth)acrylate monomer. The increased hydrophilicity of the fatty amide(meth)acrylate monomer facilitates the diffusion through the aqueous phase. The monomer synthesis is designed to be glycerol ester-free to increase long term stability for monomers and polymers.

1 . A modified fatty amide (meth)acrylate monomer of the formula: 
       
         
           
           
               
               
           
         
       
     
     
         2 . The fatty amide (meth)acrylate monomer of  claim 1  wherein the fatty acid is derived from vegetable oil. 
     
     
         3 . The fatty amide (meth)acrylate monomer of  claim 1  wherein the fatty acid is oleic, linoleic, linolenic, caprylic, capric, lauric, palmitic, stearic or eleostearic acid. 
     
     
         4 . A latex polymer comprising the polymerization product of:
 an ethylenically unsaturated monomer suitable for forming a latex composition; and   the fatty amide (meth)acrylate monomer of  claim 1 .   
     
     
         5 . The latex polymer of  claim 4  wherein the fatty acid of the modified fatty amide (meth)acrylate monomer is derived from vegetable oil. 
     
     
         6 . The latex polymer of  claim 4  wherein the fatty acid of the modified fatty amide (meth)acrylate monomer is oleic, linoleic, linolenic, caprylic, capric, lauric, palmitic, stearic or eleostearic acid. 
     
     
         7 . The latex polymer of  claim 4  wherein said ethylenically unsaturated monomer is selected from the group consisting of vinyl acetate, vinyl chloride, vinyl ester of a saturated tertiary branched carboxylic acid, acrylonitrile, acrylamide, 2-ethylhexyl acrylate, 2-ethylhexyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, glycidyl acrylate, glycidyl methacrylate, acrylic acid, methacrylic acid, butyl acrylate, butyl methacrylate, methyl methacrylate, methyl acrylate, para-acetoxystyrene, and styrene. 
     
     
         8 . A method of making a fatty amide (meth)acrylate monomer by reacting:
 the reaction product of a vegetable oil and ethanolamine or substituted ethanolamines; and   a (meth)acrylate functionalizing compound selected from the group comprising: acryloyl chloride, methacryloyl chloride, acrylic acid, methacrylic acid, and the product of hydroxyethyl (meth)acrylate reacted in equimolar proportion with isophorone diisocyanate.   
     
     
         9 . The method of  claim 8  wherein the vegetable oil is soybean oil, coconut oil or linseed oil. 
     
     
         10 . The method of  claim 8  where the substituted ethanolamine is N-methyl ethanolamine, N-oleoylethanolamine, N-ethylethanolamine, N-propylethanolamine, N-butylethanolamine, N-tert-butylethanolamine, N-(tert-butoxycarbonyl)ethanolamine, N-(allyloxycarbonyl) ethanolamine, benzyl N-(2-hydroxyethyl)carbamate, ethyl-N-(2-hydroxyethyl)-carbamate, or diethanolamine. 
     
     
         11 . A fatty amide (meth)acrylate monomer made by the method of  claim 8 . 
     
     
         12 . The fatty amide (meth)acrylate monomer of  claim 2  wherein the fatty acid is derived from vegetable oil selected from the group consisting of linseed oil, soybean oil, coconut oil, safflower oil and tung oil. 
     
     
         13 . The fatty amide (meth)acrylate monomer of  claim 1  wherein the fatty acid has at least 8 carbon atoms. 
     
     
         14 . The fatty amide (meth)acrylate monomer of  claim 1  wherein the fatty acid is unsaturated. 
     
     
         15 . The latex polymer of  claim 5  wherein the fatty acid is derived from vegetable oil selected from the group consisting of linseed oil, soybean oil, coconut oil, safflower oil and tung oil. 
     
     
         16 . The latex polymer of  claim 4  wherein the fatty acid has at least 8 carbon atoms. 
     
     
         17 . The latex polymer of  claim 4  wherein the fatty acid is unsaturated.