Non-isocyanate polyurethanes and methods of making and using the same

Patent metadata

Field	Value
Publication number	US-9957356-B2
Application number	US-201615234173-A
Country	US
Kind code	B2
Filing date	Aug 11, 2016
Priority date	Aug 17, 2015
Publication date	May 1, 2018
Grant date	May 1, 2018

Abstract

Polyurethane compositions are disclosed herein, as well as methods of making and using such polyesters. In some embodiments, the polyurethanes are formed from monomers derived from natural oils. In some embodiments, the polyurethanes are formed without the use of monomers bearing isocyanate groups.

First claim

What is claimed is:

1. A polymer, which comprises constitutional units formed from one of more compounds of Formula (I):

and constitutional units formed from one or more compounds for Formula (II):

wherein:
R 1 is —OH or —OR 2 ;
R 2 is C 1-6 alkyl or C 1-6 oxyalkyl;
X 1 is C 4-10 alkylene; and
X 2 is C 4-24 alkylene or C 4-24 heteroalkylene.

2. The polymer of claim 1 , wherein R 1 is —OH.

3. The polymer of claim 1 , wherein R 1 is —OR 2 .

4. The polymer of claim 3 , wherein R 2 is methyl, ethyl, or isopropyl.

5. The polymer of claim 3 , wherein R 2 is methyl.

6. The polymer of claim 1 , wherein R 2 is methyl, ethyl, or n-propyl.

7. The polymer of claim 1 , wherein X 1 is —(CH 2 ) 7 —.

8. The polymer of claim 1 , wherein X 2 is C 4-24 alkylene.

9. The polymer of claim 8 , wherein X 2 is —(CH 2 ) 4 —, —(CH 2 ) 6 —, —(CH 2 ) 8 —, —(CH 2 ) 10 —, —(CH 2 ) 12 —, —(CH 2 ) 14 —, —(CH 2 ) 16 —, —(CH 2 ) 18 —.

10. The polymer of claim 9 , wherein X 2 is —(CH 2 ) 12 —.

11. The polymer of claim 1 , wherein X 2 is C 4-24 heteroalkylene.

12. The polymer of claim 11 , wherein X 2 is

wherein
X 3 is C 1-6 alkylene;
X 4 is C 1-6 alkylene;
n is an integer from 1 to 500.

13. The polymer of claim 12 , wherein X 3 is —(CH 2 )—, —(CH 2 ) 2 —, —(CH 2 ) 3 —, —(CH 2 ) 4 —, —(CH 2 ) 5 —, —(CH 2 ) 6 —, —CH 2 —CH(CH 3 )—, or —CH(CH 3 )—CH 2 —.

14. The polymer of claim 13 , wherein X 3 is —(CH 2 ) 4 —.

15. The polymer of claim 12 , wherein X 4 is —(CH 2 )—, —(CH 2 ) 2 —, —(CH 2 ) 3 —, —(CH 2 ) 4 —, —(CH 2 ) 5 —, —(CH 2 ) 6 —, —CH 2 —CH(CH 3 )—, or —CH(CH 3 )—CH 2 —.

16. The polymer of claim 15 , wherein X 4 is —(CH 2 ) 4 —.

17. The polymer of claim 12 , wherein n is an integer from 80 to 120.

18. The polymer of claim 1 , wherein the one or more compounds of Formula (II) comprises:
one or more first diamine compounds wherein X 2 is —(CH 2 ) 4 —, —(CH 2 ) 6 —, —(CH 2 ) 8 —, —(CH 2 ) 10 —, —(CH 2 ) 12 —, —(CH 2 ) 14 , —(CH 2 ) 16 —, —(CH 2 ) 18 —; and
one or more second diamine compounds wherein X 2 is

wherein X 3 , X 4 , and n have the definitions recited above.

19. The polymer of claim 18 , wherein the molar ratio of constitutional units formed from the first diamine compounds to the constitutional units formed from the second diamine compound ranges from 1:100 to 100:1.

20. The polymer of claim 19 , wherein the molar ratio of constitutional units formed from the first diamine compounds to the constitutional units formed from the second diamine compound ranges from 1:10 to 10:1.

Assignees

• Elevance Renewable Sciences

Inventors

• Zhang Keren
• Nelson Ashley M
• Long Timothy E
• Bertin Paul A
• Beuhler Allyson

Classifications

• C09D175/04

  Polyurethanes · CPC title

• D06M15/564

  Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them · CPC title

• C08G71/04 Primary

  Polyurethanes · CPC title

• C09D171/00

  Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain (based on polyacetals C09D159/00; based on epoxy resins C09D163/00; based on polythioether-ethers C09D181/02; based on polyethersulfones C09D181/06); Coating compositions based on derivatives of such polymers · CPC title

• C08L75/06

  from polyesters · CPC title