Biobased cyclic carbonate functional resins and polyurethane thermosets therefrom
The invention relates to a resin having a plurality of cyclic carbonate groups comprising the reaction product of: a) an epoxidized sucrose fatty acid ester resin, and b) carbon dioxide where a) and b) are reacted under conditions sufficient to carbonylate a plurality of the oxirane groups of the epoxidized sucrose fatty acid ester resin, and optionally in the presence of a catalyst or of a solvent. In one embodiment the epoxidized sucrose fatty acid ester resin is epoxidized sucrose soyate. The invention also relates to methods for producing a resin having a plurality of cyclic carbonate groups. In a method of the invention, an epoxidized sucrose fatty acid ester resin is contacted with carbon dioxide under conditions sufficient to carbonylate a plurality of the oxirane groups of the epoxidized sucrose fatty acid ester resin, and optionally in the presence of a catalyst or of a solvent. Other embodiments of the invention relate to curable composition containing a) a resin having a plurality of cyclic carbonate groups; b) an alkyl amine curing agent having two or more reactive amine groups; and c) optionally, a catalyst; and cured compositions and articles.
1. A bio-based resin having a plurality of cyclic carbonate groups comprising the reaction product of:
a) an epoxidized sucrose fatty acid ester resin, and
b) carbon dioxide,
wherein a) and b) are reacted under conditions sufficient to carbonylate a plurality of the oxirane groups of the epoxidized sucrose fatty acid ester resin and optionally in the presence of a catalyst or of a solvent,
wherein 25%-90% of the epoxide groups of the epoxidized sucrose fatty acid ester resin are carbonylated.
2. The resin of claim 1 , wherein the epoxidized sucrose fatty acid ester resin is epoxidized sucrose soyate.
3. The resin of claim 1 , wherein substantially all of the epoxide groups of the epoxidized sucrose fatty acid ester resin are carbonylated.
4. A curable composition comprising:
a) the bio-based resin of claim 1 ;
b) an alkyl amine curing agent having two or more reactive amine groups; and
c) optionally, a catalyst.
5. The curable composition of claim 4 , wherein the alkyl amine curing agent having two or more reactive amine groups is selected from aminoethylpiperazine (AEP), 2-methyl1,5-pentanediamine (MPDA), diethylene triamine (DETA), and tris(2-aminoethyl)amine (TAEA), and bis(4-aminocyclohexyl)methane (PACM).
6. An article coated with the curable coating composition of claim 4 .
7. The resin of claim 1 , wherein 25% of the epoxide groups of the epoxidized sucrose fatty acid ester resin are carbonylated.
8. The resin of claim 1 , wherein 55% of the epoxide groups of the epoxidized sucrose fatty acid ester resin are carbonylated.
9. The resin of claim 1 , wherein 75% of the epoxide groups of the epoxidized sucrose fatty acid ester resin are carbonylated.
10. The resin of claim 1 , wherein 90% of the epoxide groups of the epoxidized sucrose fatty acid ester resin are carbonylated.
11. A method for producing a resin having a plurality of cyclic carbonate groups comprising the step of:
contacting an epoxidized sucrose fatty acid ester resin with carbon dioxide under conditions sufficient to carbonylate a plurality of the oxirane groups of the epoxidized sucrose fatty acid ester resin, and optionally in the presence of a catalyst or of a solvent,
wherein 25%-90% of the epoxide groups of the epoxidized sucrose fatty acid ester resin are carbonylated.
12. The method of claim 11 , wherein the epoxidized sucrose fatty acid ester resin is epoxidized sucrose soyate.
13. The method of claim 11 , wherein the catalyst is tetra-butyl ammonium bromide.
14. The method of claim 11 , wherein the solvent is toluene.
15. The method of claim 11 , wherein 25% of the epoxide groups of the epoxidized sucrose fatty acid ester resin are carbonylated.
16. The method of claim 11 , wherein 55% of the epoxide groups of the epoxidized sucrose fatty acid ester resin are carbonylated.
17. The method of claim 11 , wherein 75% of the epoxide groups of the epoxidized sucrose fatty acid ester resin are carbonylated.
18. The method of claim 11 , wherein 90% of the epoxide groups of the epoxidized sucrose fatty acid ester resin are carbonylated.