Renewable resins and unsaturated polyesters and methods of making the same

Patent metadata

Field	Value
Publication number	US-10280255-B2
Application number	US-201715496293-A
Country	US
Kind code	B2
Filing date	Apr 25, 2017
Priority date	Apr 26, 2016
Publication date	May 7, 2019
Grant date	May 7, 2019

Abstract

An aspect of the present disclosure is a bioderived polymer that includes a first repeat unit that includes

where n is an integer between 1 and 1000, and R 1 is a first hydrocarbon group.

First claim

What is claimed is:

1. A polymer comprising:

wherein:
the polymer includes a first amount (n) of a first repeat unit where n is an integer between 1 and 1000,
the polymer includes a second amount (m) of a second repeat unit where m is an integer between 1 and 100,
R 1 is a first hydrocarbon group, and
R 2 is a second hydrocarbon group.

2. The polymer of claim 1 , wherein the first hydrocarbon group comprises at least one of a first linear alkane or a first branched alkane.

3. The polymer of claim 2 , wherein the first linear alkane has a length between a C1 alkane and a C10 alkane, inclusively.

4. The polymer of claim 3 , wherein the first linear alkane is a C4 alkane.

5. The polymer of claim 1 , wherein the second hydrocarbon group comprises a second linear alkane having a length between a C1 alkane and a C10 alkane, inclusively.

6. The polymer of claim 5 , wherein the second linear alkane is a C4 alkane.

7. The polymer of claim 1 , further comprising:
a first terminal end and a second terminal end, wherein:
both the first terminal end and the second terminal end are selected from the group consisting of a hydroxyl group and a carboxylic acid group.

8. The polymer of claim 1 , wherein a molar amount of the first repeat unit incorporated into the polymer is between 2.0 mol % and 100 mol %.

9. The polymer of claim 1 , wherein the polymer has a melting point between 30° C. and 260° C.

10. The polymer of claim 1 , wherein the polymer has no melting point.

11. The polymer of claim 1 , wherein the polymer has a glass transition temperature between −100° C. and 75° C.

12. The polymer of claim 1 , wherein the polymer has a weight average molecular weight between 1×10 3 and 1×10 6 .

13. The polymer of claim 1 , wherein at least a portion of the carbon of the first repeat unit is bioderived.

14. The polymer of claim 13 , wherein the bioderived portion of the carbon is determined to be bioderived according to ASTM D866.

15. A resin comprising:

wherein:
n is an integer between 1 and 1000,
R 1 is a first hydrocarbon group,
m is an integer between 1 and 100,
R 2 is a second hydrocarbon group, and
R 3 is a third hydrocarbon group.

16. A method comprising a first reacting of a first polymer comprising

with muconic acid to form a second polymer comprising

wherein:
in is an integer between 1 and 100,
n is an integer between 1 and 1000,
R 1 is a first hydrocarbon group, and
R 2 is a second hydrocarbon group.

17. The method of claim 16 , wherein the muconic acid is bioderived.

18. The method of claim 16 , further comprising mixing benzoate with a strain of Pseudomonas Putida , wherein the Pseudomonas Putida metabolizes the benzoate to produce the muconic acid.

19. The method of claim 16 , wherein:
the first polymer comprises

and
the first reacting comprises transesterification of the first polymer with the muconic acid to further produce R 1 OH.

20. The method of claim 19 , wherein:
the first reacting further comprises a starting polymer comprising

x is an integer between 1 and 100 and x is less than m, and
the starting polymer reacts by condensation to produce the first polymer and water.

21. The method of claim 20 , wherein:
the first reacting further comprises a diol and dicarboxylic acid, and
the diol and the dicarboxylic acid react by condensation to produce the starting polymer.

22. The method of claim 21 , wherein at least one of the diol or the dicarboxylic acid is bioderived.

23. The method of claim 16 , further comprising a second reacting of the second polymer with a crosslinker comprising a vinyl-terminated hydrocarbon to form a resin.

24. The method of claim 23 , wherein the resin comprises

wherein
R 3 is a benzene ring.

Assignees

• Alliance Sustainable Energy
• Colorado School Of Mines

Inventors

• Beckham Gregg Tyler
• Vardon Derek R
• RORRER Nicholas
• Dorgan John R

Classifications

• G01R33/4633

  Sequences for multi-dimensional NMR · CPC title

• C08G63/52 Primary

  Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation · CPC title

• C08K5/0025 Primary

  Crosslinking or vulcanising agents; including accelerators · CPC title

• C08L31/06

  Homopolymers or copolymers of esters of polycarboxylic acids · CPC title

• C08L25/06

  Polystyrene · CPC title