Beta-propiolactone based copolymers containing biogenic carbon, methods for their production and uses thereof

Patent metadata

Field	Value
Publication number	US-10144802-B2
Application number	US-201615369764-A
Country	US
Kind code	B2
Filing date	Dec 5, 2016
Priority date	Dec 5, 2016
Publication date	Dec 4, 2018
Grant date	Dec 4, 2018

Abstract

Provided herein are methods and systems for producing biodegradable beta-propoiolacone-based polyester polymers from renewable EO and CO on an industrial scale.

First claim

What is claimed is:

1. A copolymer comprising beta-propiolactone monomers and at least one beta-lactone co-monomer wherein the copolymer has a biocontent of at least 50 percent.

2. The copolymer of claim 1 wherein the copolymer has a biocontent of at least 50% and optionally at least 75 percent.

3. The copolymer of claim 1 wherein the copolymer is a linear polymer including an anionic nucleophile with the formula R x O(C═O)O − and cationic chain ends wherein R x is, independently, selected from hydrogen, optionally substituted aliphatic, optionally substituted heteroaliphatic, optionally substituted aryl and optionally substituted heteroaryl.

4. The polymer of claim 3 wherein the anionic nucleophile is at least one compound with the formula CH 2 ═CHCO 2 —, or CH 3 CO 2 —.

5. The polymer of claim 3 wherein the cation is selected from the group consisting of Li + , Na + , K + , Mg 2+ , Ca 2+ , Al 3+ and Na + .

6. The copolymer of claim 3 wherein the cation is an organic cation.

7. The copolymer of claim 6 wherein the organic cation is selected from the group consisting of quaternary ammonium, imidazolium, bis(triphenylphosphine)iminium and tetraalkyl ammonium.

8. The copolymer of claim 1 wherein the comonomer is derived from a beta lactone.

9. The copolymer of claim 1 wherein the copolymer it is forms at least part of a sanitary product.

10. The copolymer of claim 1 wherein the copolymer is formed into at least part of a structural product.

11. The copolymer of claim 1 wherein the copolymer is a linear polymer.

12. The copolymer of claim 1 wherein the betalactone is selected from the group consisting of beta-butyrolactone, beta-valerolactone, beta-heptanolactone, beta-tridecanolactone, cis-3,4-dimethyloxetan-2-one, 4-(but-3-en-1-yl)oxetan-2-one, 4-(butoxymethyl)-2-oxetanone,
4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-2-oxetanone,
4-[(2-propen-1-yloxy)methyl]-2-oxetanone, 4-[(benzoyloxy)methyl]-2-Oxetanone.

13. The copolymer of claim 1 wherein the copolymer has a biodegradability equal to the monomer and co-monomer.

14. The copolymer of claim 13 wherein the copolymer has a biodegradability of at least 50% and optionally at least 80%.

Assignees

• Novomer Inc

Inventors

• Sookraj Sadesh H

Classifications

• C08G63/08 Primary

  Lactones or lactides · CPC title

• C08G63/6882

  derived from hydroxy carboxylic acids · CPC title

• C08G63/664 Primary

  derived from hydroxy carboxylic acids · CPC title

• C07D305/12

  Beta-lactones · CPC title