Polyurethane materials formed from unsaturated plant oils via an alkyne zipper reaction

Patent metadata

Field	Value
Publication number	US-9732181-B2
Application number	US-201514964261-A
Country	US
Kind code	B2
Filing date	Dec 9, 2015
Priority date	Dec 9, 2015
Publication date	Aug 15, 2017
Grant date	Aug 15, 2017

Abstract

A process of forming a polyurethane material includes forming an alkyne-terminated triglyceride material from an unsaturated plant oil. The process also includes forming a hydroxyl-terminated polyol material from the alkyne-terminated triglyceride material. The process further includes polymerizing a mixture that includes the hydroxyl-terminated polyol material to form a polyurethane material.

First claim

The invention claimed is:

1. A process of forming a polyurethane material, the process comprising:
forming an alkyne-terminated triglyceride material from an unsaturated plant oil via an alkyne zipper reaction;
forming a hydroxyl-terminated polyol material from the alkyne-terminated triglyceride material by converting terminal alkynes of the alkyne-terminated triglyceride material to hydroxyl groups; and
polymerizing a mixture that includes the hydroxyl-terminated polyol material to form a polyurethane material.

2. The process of claim 1 , wherein the unsaturated plant oil includes an unsaturated vegetable oil.

3. The process of claim 1 , wherein the unsaturated plant oil includes:
a first fatty acid chain having at least one carbon-carbon double bond;
a second fatty acid chain having at least one carbon-carbon double bond; and
a third fatty acid chain.

4. The process of claim 3 , wherein the first fatty acid chain has at least two carbon-carbon double bonds.

5. The process of claim 4 , wherein the second fatty acid chain has at least two carbon-carbon double bonds.

6. The process of claim 3 , wherein the third fatty acid chain has at least one carbon-carbon double bond.

7. The process of claim 6 , wherein the third fatty acid chain has at least two carbon-carbon double bonds.

8. The process of claim 1 , wherein the hydroxyl-terminated polyol material includes a terminal hydroxyl group associated with each fatty acid chain of the unsaturated plant oil.

9. The process of claim 1 , wherein polymerizing the mixture that includes the hydroxyl-terminated polyol material comprises adding a diisocyanate material to the mixture.

10. The process of claim 9 , wherein polymerizing the mixture that includes the hydroxyl-terminated polyol material further comprises adjusting an amount of diisocyanate material in the mixture to adjust a degree of cross-linking in the polyurethane material.

11. The process of claim 9 , wherein the diisocyanate material includes methylene diphenyl diisocyanate (MDI), toluene diisocyanate (TDI), hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), pentamethylene diisocyanate (PDI), or a combination thereof.

12. A biorenewable polyurethane material formed by a process comprising:
forming an alkyne-terminated triglyceride material from an unsaturated plant oil via an alkyne zipper reaction;
forming a hydroxyl-terminated polyol material from the alkyne-terminated triglyceride material by converting terminal alkynes of the alkyne-terminated triglyceride material to hydroxyl groups; and
polymerizing a mixture that includes the hydroxyl-terminated polyol material to form a biorenewable polyurethane material.

13. The biorenewable polyurethane material of claim 12 , wherein each fatty acid chain of the unsaturated plant oil includes at least one carbon-carbon double bond, and wherein the hydroxyl-terminated polyol material includes a terminal hydroxyl group associated with each fatty acid chain of the unsaturated plant oil.

14. The biorenewable polyurethane material of claim 13 , wherein at least one fatty acid chain of the unsaturated plant oil includes a plurality of carbon-carbon double bonds, wherein a first carbon-carbon double bond of the plurality of carbon-carbon double bonds is associated with formation of the terminal hydroxyl group, and wherein one or more additional carbon-carbon double bonds of the plurality of carbon-carbon double bonds are associated with formation of one or more secondary hydroxyl groups.

15. The biorenewable polyurethane material of claim 12 , wherein a first fatty acid chain of the unsaturated plant oil has a first number of carbon-carbon double bonds, and wherein a second fatty acid chain of the unsaturated plant oil has a second number of carbon-carbon double bonds, wherein the first number of carbon-carbon double bonds is different from the second number of carbon-carbon double bonds.

16. The biorenewable polyurethane material of claim 12 , wherein biorenewable polyurethane material is a cross-linked biorenewable polyurethane material.

17. An acoustic dampening foam comprising a mixture of:
a petroleum-based first polyurethane material; and
a second polyurethane material distinct from the first polyurethane material, the second polyurethane material formed by a process that includes:
forming an alkyne-terminated triglyceride material from an unsaturated plant oil via an alkyne zipper reaction;
forming a hydroxyl-terminated polyol material from the alkyne-terminated triglyceride material by converting alkynes of the alkyne-terminated triglyceride material to hydroxyl groups; and
polymerizing a reaction mixture that includes the hydroxyl-terminated polyol material to form a cross-linked polyurethane material, wherein the reaction mixture includes a diisocyanate material.

18. The acoustic dampening foam of claim 17 , wherein a weight of the second polyurethane material is not less than 10 percent of a weight of the acoustic dampening foam.

Assignees

• IBM

Inventors

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

Classifications

• C08G2350/00

  Acoustic or vibration damping material · CPC title

• C07C67/31

  by introduction of functional groups containing oxygen only in singly bound form · CPC title

• C08G18/72

  Polyisocyanates or polyisothiocyanates · CPC title

• C08G2101/00

  Manufacture of cellular products · CPC title

• C07C69/67

  of saturated acids · CPC title