Renewably derived polyesters and methods of making and using the same
View Patent ↗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 have lower glass transition temperatures than polyesters of comparable molecular weight.
1. A polyester polymer, which comprises constitutional units formed from a reaction mixture comprising a first monomer, a second monomer, and a third monomer, each of Formula (I):
wherein:
the first monomer is a compound of Formula (I) where R 2 is methyl, X 1 is —(CH 2 ) 7 —, R 1 is —OH or —OR 3 , and R 3 is C 1-6 alkyl or C 1-6 oxyalkyl;
the second monomer is a compound of Formula (I) where R 2 is ethyl, X 1 is —(CH 2 ) 6 —, R 1 is —OH or —OR 3 , and R 3 is C 1-6 alkyl or C 1-6 oxyalkyl; and
the third monomer is a compound of Formula (I) where R 2 is n-propyl, X 1 is —(CH 2 ) 5 —, R 1 is —OH or —OR 3 , and R 3 is C 1-6 alkyl or C 1-6 oxyalkyl.
2. The polyester polymer of claim 1 , wherein R 1 is —OH.
3. The polyester polymer of claim 1 , wherein R 1 is —OR 3 .
4. The polyester polymer of claim 1 , which comprises constitutional units formed from the first monomer and the second monomer.
5. The polyester polymer of claim 1 , which comprises constitutional units formed from the first monomer and the third monomer.
6. The polyester polymer of claim 1 , which comprises constitutional units formed from the second monomer and the third monomer.
7. The polyester polymer of claim 1 , which comprises constitutional units formed from the first monomer, the second monomer, and the third monomer.
8. The polyester polymer of claim 1 , which is an AB-type polymer.
9. The polyester polymer of claim 1 , wherein the polyester polymer is amorphous.
10. The polyester polymer of claim 1 , wherein the reaction mixture further comprises one or more diols.
11. The polyester polymer of claim 10 , 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.
12. The polyester polymer of claim 1 , wherein the reaction mixture further comprises one or more diacids, or esters thereof.
13. The polyester polymer of claim 12 , 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.
14. The polyester polymer of claim 1 , wherein the reaction mixture further comprises one or more hydroxy acids, or esters thereof.
15. The polyester polymer of claim 14 , 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.
16. The polyester polymer of claim 1 , wherein the reaction mixture further comprises one or more branching agents.
17. The polyester polymer of claim 1 , wherein the reaction mixture further comprises one or more cross-linking agents.