Renewable resins and unsaturated polyesters and methods of making the same
View Patent ↗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.
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.