Polyisocyanates from fused bicyclic polyols and polyurethanes therefrom

Patent metadata

Field	Value
Publication number	US-9556293-B2
Application number	US-201314434710-A
Country	US
Kind code	B2
Filing date	Oct 15, 2013
Priority date	Oct 15, 2012
Publication date	Jan 31, 2017
Grant date	Jan 31, 2017

Abstract

The present invention is directed to polyisocyanates and polyurethanes derived therefrom. In various embodiments, the present invention provides polyisocyanates, methods of making the polyisocyanates from fused bicyclic alcohols, polyurethanes, and methods of making the polyurethanes from the polyisocyanates.

First claim

We claim:

1. A polyurethane comprising a plurality of subunits each having the structure of Formula (II)

wherein fused rings A and B are each independently selected from (C 5 -C 10 )cycloalicyl and (C 2 -C 10 )heterocyclyl;
m and n are each independently 1-8;
R′ is selected from the group consisting of (C 2 -C 10 )alkanylene, (C 2 -C 10 )alkenylene, and (C 2 -C 10 )alkynylene, wherein R′ is unsubstituted or substituted; and
fused rings A and B are each independently unsubstituted or substituted.

2. The polyurethane of claim 1 , wherein R′ is —CH 2 —CH 2 —.

3. The polyurethane of claim 1 , wherein Formula (II) is:

4. The polyurethane of claim 1 , wherein Formula (II) is:

5. The polyurethane of claim 1 , wherein Formula (II) is:

6. The polyurethane of claim 1 , wherein Formula (II) is:

7. The polyurethane of claim 1 , wherein Formula (II) is:

8. The polyurethane of claim 1 , wherein Formula (II) is:

9. The polyurethane of claim 1 , wherein Formula (II) is:

10. The polyurethane of claim 1 , wherein Formula (II) is:

11. The polyurethane of claim 1 , wherein the polyurethane is derived from a compound of Formula (I):

wherein fused rings A and B are each independently selected from (C 5 -C 10 )cycloalkyl and (C 2 -C 10 )heterocyclyl;
m and n are each independently 1-8;
R′ of Formula (I) is selected from the group consisting of (C 2 -C 10 )alkanylene, (C 2 -C 10 )alkenylene, and (C 2 -C 10 )alkynylene, wherein R′ is unsubstituted or substituted;
R″ is selected from the group consisting —C(O)OH, —C(O)O − X + , —C(O)F, —C(O)Cl, —C(O)Br, —C(O)I, —C(O)N 3 , and —NCO, wherein X + is a counterion; and
fused rings A and B of Formula (I) are each independently unsubstituted or substituted.

12. The polyurethane of claim 11 , wherein the polyurethane comprises a reaction product of the compound of Formula (I) and an alcohol, wherein R″ is —NCO.

13. The polyurethane of claim 12 , wherein the alcohol comprises a polyol comprising a polyether polyol, a polyester polyol, or a combination thereof.

14. The polyurethane of claim 11 , wherein the compound of Formula (I) is

15. The polyurethane of claim 11 , wherein the compound of Formula (I) is

16. The polyurethane of claim 11 , wherein the compound of Formula (I) is

17. The polyurethane of claim 11 , wherein the compound of Formula (I) is

18. The polyurethane of claim 11 , wherein the compound of Formula (I) is

19. A method of making the polyurethane of claim 1 comprising contacting a compound of Formula (I) with an alcohol to provide the polyurethane, wherein the compound of Formula (I) has the structure:

wherein fused rings A and B are each independently selected from (C 5 -C 10 )cycloalkyl and (C 2 -C 10 )heterocyclyl;
m and n are each independently 1-8;
R′ of Formula (I) is selected from the group consisting of (C 2 -C 10 )alkanylene, (C 2 -C 10 ) alkanylene, and (C 2 -C 10 )alkynylene, wherein R′ is unsubstituted or substituted;
R″ is —NCO; and
fused rings A and B of Formula (I) are each independently unsubstituted or substituted.

20. An aqueous dispersion comprising the polyurethane of claim 1 .

Assignees

• Univ Iowa State Res Found Inc

Inventors

• Chen Jason Shih-Hao
• Kessler Michael Richard
• Zenner Michael Dennis

Classifications

• C08L2201/50

  Aqueous dispersion, e.g. containing polymers with a glass transition temperature (Tg) above 20°C · CPC title

• C09J4/00

  Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16} · CPC title

• C08G18/3218

  containing cyclic groups having at least one oxygen atom in the ring · CPC title

• C07D493/04 Primary

  Ortho-condensed systems · CPC title

• C08G18/771

  oxygen · CPC title