Ketal ester derivatives
The present disclosure relates to the preparation of acrylate, alkacrylate, allyl, and polycarbonate derivatives of hydroxy ketal esters, and uses thereof.
1. A polycarbonate one or more repeat units IA, IB, or a combination thereof:
wherein
R 1 is a divalent linear, branched, or cyclic alkyl group having 1 to 36 carbon atoms, a linear or branched alkenyl group having 1 to 36 carbon atoms, an aryl group, or an alkaryl group having from 7 to 36 carbon atoms;
R 2 is a covalent bond or a linear, branched, or cyclic alkyl group having 1 to 18 carbon atoms, a linear or branched alkenyl group having 1 to 18 carbon atoms, an aryl group, or an alkaryl group having from 7 to 18 carbon atoms;
R 3 is hydrogen, alkynyl, or a linear, branched, or cyclic alkyl group having 1 to 18 carbon atoms, a linear or branched alkenyl group having 1 to 18 carbon atoms, an aryl group, or an alkaryl group having from 7 to 18 carbon atoms;
R 4 is a group having the formula
wherein
a is 0 or 1 and
R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are independently hydrogen, alkynyl, or linear, branched, or cyclic alkyl groups having 1 to 18 carbon atoms, linear or branched alkenyl groups having 1 to 18 carbon atoms, aryl groups, or alkaryl groups having from 7 to 18 carbon atoms;
α and α′ are independently integers of 1 to about 100; and
γ is an integer of 1 to about 30 and γ is the same or different for repeat unit IA and repeat unit IB.
2. The polycarbonate of claim 1 wherein R 1 further comprises one or more functional groups comprising halogen, tertiary amine, hydroxyl, carbonate, carboxylic acid, carboxylic ester, ether, carbonyl, ketal, urethane, imide, amide, or a combination thereof.
3. The polycarbonate of claim 1 wherein repeating units IA, IB, or both further comprise hydroxyl functional endgroups.
4. The polycarbonate of claim 1 wherein one or more α, α′, or both are independently between 0 and about 5.
5. The polycarbonate of claim 1 wherein R 2 is —(CH 2 ) 2 —, and R 3 is —CH 3 , and R 4 is the residue of glycerol.
6. The polycarbonate of claim 1 wherein about 25% by weight or more of the compound is biomass based.
7. The polycarbonate of claim 1 wherein between about 25% and 90% by weight of the compound is biomass based.
8. The polycarbonate of claim 1 wherein between about 40% and 75% by weight of the compound is biomass based.
9. The polycarbonate of claim 1 wherein the compound is biodegradable.
10. The polycarbonate of claim 1 wherein one or more values of γ is between about 1 and 10 and repeat units IA, IB, or both further comprise hydroxyl functional endgroups.
11. The polycarbonate of claim 1 , wherein one or more γ is between about 1 and 10 and repeat units IA, IB, or both further comprise one or more repeat units comprising a polyurethane moiety.
12. The polycarbonate of claim 1 wherein
R 2 is —(CH 2 ) 2 —, R 3 is —CH 3 , and R 4 is the residue of glycerol; and
one or more α, α′, or both are independently between 0 and about 5.
13. The polycarbonate of claim 12 wherein repeat units IA, IB, or both further comprise hydroxyl functional endgroups.