Beta-propiolactone based copolymers containing biogenic carbon, methods for their production and uses thereof
Provided herein are methods and systems for producing biodegradable beta-propiolactone-based polyester polymers from renewable EO and CO on an industrial scale.
1. A copolymer comprising beta-propiolactone monomers and at least one co-monomer comprising (i) anhydride or (ii) alcohol comprising at least two hydroxyl groups,
wherein the copolymer has a bio-content of at least 10%, and
wherein the copolymer is a linear polymer comprising an anionic nucleophile and cationic chain ends.
2. The copolymer of claim 1 , wherein the at least one co-monomer has a bio-content.
3. The copolymer of claim 1 , wherein the at least one co-monomer has a bio-content of at least 50%.
4. The copolymer of claim 1 , wherein the copolymer has a bio-content of at least 50%.
5. The copolymer of claim 1 , wherein the anionic nucleophile comprises R x O − , R x C(═O)O − , R x S − , R x O(C═O)O − , R x (SO 2 )O − or PR x 3 O − , or any combination thereof, wherein each R x is independently hydrogen, optionally substituted aliphatic, optionally substituted heteroaliphatic, optionally substituted aryl, or and optionally substituted heteroaryl.
6. The copolymer of claim 1 , wherein the anionic nucleophile comprises R x O − , wherein R x is H, optionally substituted aliphatic, optionally substituted heteroaliphatic, optionally substituted aryl, and or optionally substituted heteroaryl.
7. The copolymer of claim 1 , wherein the anionic nucleophile comprises a hydroxide, methoxide, or ethoxide.
8. The copolymer of claim 1 , wherein the anionic nucleophile comprises a halide.
9. The copolymer of claim 1 , wherein the anionic nucleophile is CH 2 ═CHCO 2 − , CH 3 CO 2 − , or CF 3 CO 2 .
10. The copolymer of claim 1 , wherein the cationic chain ends comprise Li + , Na + , K + , Mg 2+ , Ca 2+ , or Al 3+ .
11. The copolymer of claim 1 , wherein the cationic chain ends comprise an organic cation.
12. The copolymer of claim 11 , wherein the organic cation comprises quaternary ammonium, imidazolium, bis(triphenylphosphine)iminium or tetraalkyl ammonium.
13. The copolymer of claim 1 , wherein the copolymer forms at least part of a sanitary product.
14. The copolymer of claim 1 , wherein the copolymer is formed into at least part of a structural product.
15. The copolymer of claim 1 , wherein the anhydride is a cyclic anhydride.
16. The copolymer of claim 15 , wherein the cyclic anhydride is succinic anhydride, or and maleic anhydride, or both.
17. The copolymer of claim 1 , wherein the alcohol comprising at least two hydroxyl groups is a diol.
18. The copolymer of claim 17 , wherein the diol is ethylene glycol, propylene glycol, 1,4-butanediol, diethylene glycol, or bis(hydroxymethyl)octadecanol,1,6-hexanediol, or any combination thereof.
19. The copolymer of claim 1 , wherein the copolymer has a bio-content of at least 75%.
20. The copolymer of claim 1 , wherein the copolymer has a bio-content of at least 95%.
21. The copolymer of claim 1 , wherein the beta-propiolactone monomer units are derived from the carbonylation of ethylene oxide with carbon monoxide.
22. The copolymer of claim 21 , wherein the ethylene oxide has a bio-content greater than 10%.
23. The copolymer of claim 21 , wherein the carbon monoxide has a bio-content greater than 10%.