Polymeric materials formed from polyhydroxyalkanoate materials

Patent metadata

Field	Value
Publication number	US-10040894-B2
Application number	US-201615082843-A
Country	US
Kind code	B2
Filing date	Mar 28, 2016
Priority date	Mar 28, 2016
Publication date	Aug 7, 2018
Grant date	Aug 7, 2018

Abstract

In an example, a process includes chemically reacting a polyhydroxyalkanoate (PHA) material having a carboxylic-acid terminated side-chain with an azide material to form a polyisocyanate material.

First claim

The invention claimed is:

1. A process comprising chemically reacting a polyhydroxyalkanoate (PHA) material having carboxylic-acid terminated side-chains with an azide material to form a polyisocyanate material.

2. The process of claim 1 , further comprising forming the PHA material having the carboxylic-acid terminated side-chains from a PHA material having hydroxyl-terminated side-chains.

3. The process of claim 2 , further comprising:
forming a PHA material having vinyl-terminated side-chains from a vinyl-terminated fatty acid via a bacterial fermentation process; and
converting a vinyl group of a plurality of the vinyl-terminated side-chains to a hydroxyl group to form the PHA material having the hydroxyl-terminated side-chains.

4. The process of claim 3 , wherein the vinyl-terminated fatty acid includes a biorenewable vinyl-terminated fatty acid.

5. The process of claim 4 , wherein the biorenewable vinyl-terminated fatty acid is formed from a biorenewable plant oil.

6. The process of claim 5 , wherein the biorenewable plant oil includes castor oil, linseed oil, soybean oil, or a combination thereof.

7. The process of claim 4 , wherein the biorenewable vinyl-terminated fatty acid includes 10-undecenoic acid.

8. The process of claim 1 , further comprising chemically reacting the polyisocyanate material with a polyol to form a polyurethane material.

9. The process of claim 8 , wherein the polyol includes a biorenewable polyol.

10. The process of claim 9 , wherein the polyol further includes ethylene glycol, propylene glycol, butylene glycol, pentylene glycol, or a combination thereof.

11. The process of claim 1 , wherein chemically reacting the PHA material with the azide material includes forming acid azide molecules as an intermediate material, and wherein the acid azide molecules undergo a Curtius rearrangement to form the polyisocyanate material.

12. The process of 1 , wherein the azide material includes diphenylphosphoryl azide.

13. A process of forming a polyurethane material, the process comprising:
chemically reacting a polyhydroxyalkanoate (PHA) material having carboxylic-acid terminated side-chains with an azide material to form a polyisocyanate material; and
chemically reacting the polyisocyanate material with a polyol to form a polyurethane material.

14. The process of claim 13 , further comprising forming the PHA material having the carboxylic-acid terminated side-chains from a PHA material having hydroxyl-terminated side-chains.

15. The process of claim 14 , further comprising:
forming a PHA material having vinyl-terminated side-chains from a biorenewable vinyl-terminated fatty acid via a bacterial fermentation process; and
converting a vinyl group of a plurality of the vinyl-terminated side-chains to a hydroxyl group to form the PHA material having the hydroxyl-terminated side-chains.

16. The process of claim 15 , wherein the biorenewable vinyl-terminated fatty acid includes 10-undecenoic acid.

17. The process of claim 13 , wherein the polyol includes a biorenewable polyol.

18. The process of claim 17 , wherein the polyol further includes ethylene glycol, propylene glycol, butylene glycol, pentylene glycol, or a combination thereof.

19. An acoustic dampening foam comprising:
a petroleum-based polyurethane material; and
a biorenewable polyurethane material formed by a process that includes:
chemically reacting a polyhydroxyalkanoate (PHA) material having carboxylic-acid terminated side-chains with an azide material to form a polyisocyanate material; and
chemically reacting the polyisocyanate material with a polyol to form the biorenewable polyurethane material.

20. The acoustic dampening foam of claim 19 , wherein the biorenewable polyurethane material is not less than 10 weight percent of the acoustic dampening foam.

Assignees

• IBM

Inventors

• King Scott B
• Kobilka Brandon M
• Kuczynski Joseph
• Wertz Jason T

Classifications

• C08J2475/04

  Polyurethanes · CPC title

• C08G18/3206

  aliphatic · CPC title

• C08G2350/00

  Acoustic or vibration damping material · CPC title

• G10K11/162

  Selection of materials · CPC title

• C08L69/00

  Compositions of polycarbonates; Compositions of derivatives of polycarbonates · CPC title