Renewably derived polyesters and methods of making and using the same

Patent metadata

Field	Value
Publication number	US-10280254-B2
Application number	US-201715487174-A
Country	US
Kind code	B2
Filing date	Apr 13, 2017
Priority date	Apr 20, 2016
Publication date	May 7, 2019
Grant date	May 7, 2019

Abstract

Polyester compositions are disclosed herein, as well as methods of making and using such polyesters. In some embodiments, the polyesters are formed from monomers derived from natural oils. In some embodiments, the polyesters are highly branched polymers, such as highly branched polymers that have low viscosity at higher molecular weights.

First claim

What is claimed is:

1. A polyester polymer, which comprises constitutional units formed from a reaction mixture comprising one of more monomers of Formula (I):

wherein:
R 1 is —OH or —OR 2 ;
R 2 is C 1-6 alkyl or C 1-6 oxyalkyl; and
X 1 is C 4-10 alkylene.

2. The polyester polymer of claim 1 , wherein R 1 is —OH.

3. The polyester polymer of claim 1 , wherein R 1 is —OR 2 .

4. The polyester polymer of claim 3 , wherein R 2 is methyl, ethyl, or isopropyl.

5. The polyester polymer of claim 3 , wherein R 2 is methyl.

6. The polyester polymer of claim 1 , wherein X 1 is —(CH 2 ) 7 —.

7. The polyester polymer of claim 1 , wherein the reaction mixture further comprises monomers of Formula (II):

wherein:
x 2 is C 2-12 alkylene or C 2-12 oxyalkylene.

8. The polyester polymer of claim 7 , wherein X 2 is —(CH 2 ) 2 —, —(CH 2 ) 4 —, or —(CH 2 ) 6 —.

9. The polyester polymer of claim 8 , wherein X 2 is —(CH 2 ) 4 —.

10. The polyester polymer of claim 7 , wherein the molar ratio of constitutional units formed from monomers of Formula (I) to constitutional units formed from monomers of Formula (II) is from 1:5 to 20:1.

11. The polyester polymer of claim 1 , wherein the reaction mixture comprises one or more diols.

12. The polyester polymer of claim 11 , wherein the one or more diols are selected from the group consisting of ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, 1,4-butanediol, 2,3-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,8-octanediol, 2-methyl-1,3-propanediol, 2-butyl-2-ethyl-1,3-propanediol, and neopentyl glycol.

13. The polyester polymer of claim 1 , wherein the reaction mixture further comprises one or more diacids, or esters thereof.

14. The polyester polymer of claim 13 , wherein the one or more diacids, or esters thereof, are selected from the group consisting of oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, 1,12-dodecanedioic acid, 1,14-tetradecanedioic acid, 1,16-hexadecanedioic acid, 1,18-octadecanedioic acid, 1,20-eicosanedioic acid, 1,22-docosanedioic acid, 1,18-octadec-9-enedioic acid, and esters of any of the foregoing.

15. The polyester polymer of claim 1 , wherein the reaction mixture further comprises one or more hydroxy acids, or esters thereof.

16. The polyester polymer of claim 15 , wherein the one or more hydroxy acids, or esters thereof, are selected from the group consisting of α-hydroxy acids, β-hydroxy acids, ω-hydroxy acids, and esters of any of the foregoing.

17. The polyester polymer of claim 1 , which is a highly branched polymer.

18. The polyester polymer of claim 1 , wherein the polymer is biodegradable.

19. The polyester polymer of claim 1 , wherein the reaction mixture further comprises one or more branching agents.

20. The polyester polymer of claim 1 , wherein the reaction mixture further comprises one or more cross-linking agents.

Assignees

• Elevance Renewable Sciences

Inventors

• Nelson Ashley M
• Zhang Keren
• Long Timothy E
• Bertin Paul A

Classifications

• C08L67/04

  Polyesters derived from hydroxycarboxylic acids, e.g. lactones (C08L67/06 takes precedence) · CPC title

• C08G63/06 Primary

  derived from hydroxycarboxylic acids · CPC title

• C08G63/44

  Polyamides; Polynitriles · CPC title

• C08L67/02

  Polyesters derived from dicarboxylic acids and dihydroxy compounds (C08L67/06 takes precedence) · CPC title

• C08G63/6852

  derived from hydroxy carboxylic acids · CPC title