Natural Oil Derivatives Including (Meth)acrylate Functional Groups

Abstract

A compound has Structure I: where R 1 and R 2 independently are C 2 -C 12 alkyl groups, R 3 and R 3 ′ independently are H or CH 3 , X 1 is a C 4 -C 28 alkyl or alkenyl group, and R 4 is H or a N,N-bis((meth)acryloylalkyl)-amide group having Structure II: where R 5 and R 6 independently are C 2 -C 12 alkyl groups, and R 3 ″ and R 3 ′″ independently are either H or CH 3 .

1 - 31 . (canceled) 
     
     
         32 . A method of forming a (meth)acrylate natural oil derivative, comprising:
 providing a natural oil composition comprising unsaturated glycerides;   reacting the unsaturated glycerides of the natural oil composition in the presence of a metathesis catalyst to form glyceride oligomers;   reacting the glyceride oligomers of with a bis(hydroxyalkyl) amine to form bis(hydroxyalkyl) amidated glyceride oligomers; and   reacting the bis(hydroxyalkyl) amidated glyceride oligomers with an acryloyl halide, a methacryloyl halide, or a combinations thereof, to form the (meth)acrylate natural oil derivative.   
     
     
         33 . The method of  claim 32 , wherein the natural oil composition comprises vegetable oil, algal oil, animal fat, tall oil, or any mixtures thereof. 
     
     
         34 . The method of  claim 33 , wherein the natural oil composition comprises vegetable oil. 
     
     
         35 . The method of  claim 34 , wherein the vegetable oil is canola oil, rapeseed oil, coconut oil, corn oil, cottonseed oil, olive oil, palm oil, peanut oil, safflower oil, sesame oil, soybean oil, sunflower oil, linseed oil, palm kernel oil, tung oil, jatropha oil, mustard oil, camelina oil, pennycress oil, castor oil, and any combinations thereof. 
     
     
         36 . The method of  claim 35 , wherein the vegetable oil is soybean oil. 
     
     
         37 . The method of  claim 32 , wherein the glyceride oligomers comprise metathesis dimers of unsaturated glycerides, metathesis trimers of unsaturated glycerides, metathesis tetramers of unsaturated glycerides, metathesis pentamers of unsaturated glycerides, metathesis hexamers of unsaturated glycerides, or any combinations thereof. 
     
     
         38 . The method of  claim 32 , wherein the bis(hydroxyalkyl) amine is diethanolamine. 
     
     
         39 . The method of  claim 32 , wherein the metathesized natural oil derivative is formed by reacting the bis(hydroxyalkyl) amidated glyceride oligomers with an acryloyl halide. 
     
     
         40 . The method of  claim 39 , wherein the acryloyl halide is acryloyl chloride, acryloyl bromide, acryloyl iodide, or any combinations thereof. 
     
     
         41 . The method of  claim 32 , wherein the metathesized natural oil derivative is formed by reacting the bis(hydroxyalkyl) amidated glyceride oligomers with an methacryloyl halide. 
     
     
         42 . The method of  claim 41 , wherein the methacryloyl halide is methacryloyl chloride, methacryloyl bromide, methacryloyl iodide, or any combinations thereof. 
     
     
         43 . A method of forming a (meth)acrylate polymer, comprising:
 providing a reactant composition comprising a first monomer, which is a (meth)acrylate natural oil derivative formed by the method of  claim 32 , and a polymerization initiator; and   forming a (meth)acrylate polymer comprising one or more constitutional units formed from the first monomer.   
     
     
         44 . The method of  claim 43 , wherein the reactant composition further comprises a second monomer, and wherein the (meth)acrylate polymer further comprises one or more constitutional units formed from the second monomer. 
     
     
         45 . The method of  claim 44 , wherein the second monomer is selected from the group consisting of: ethylene, styrenes, halogenated vinyl compounds, acrylates, acrylamide, acrylonitrile, N-vinyl pyrrolidone, and combinations thereof. 
     
     
         46 . The method of  claim 43 , wherein the polymerization initiator is free-radical polymerization initiator, a cationic polymerization initiator, an anionic polymerization initiator, or any combinations thereof.