Polyisobutylenes and process for making same

Patent metadata

Field	Value
Publication number	US-9587067-B2
Application number	US-201514879896-A
Country	US
Kind code	B2
Filing date	Oct 9, 2015
Priority date	Nov 30, 2006
Publication date	Mar 7, 2017
Grant date	Mar 7, 2017

Abstract

The present invention generally relates to alcohol-terminated polyisobutylene (PIB) compounds, and to a process for making such compounds. In one embodiment, the present invention relates to primary alcohol-terminated polyisobutylene compounds, and to a process for making such compounds. In still another embodiment, the present invention relates to polyisobutylene compounds that can be used to synthesize polyurethanes, to polyurethane compounds made via the use of such polyisobutylene compounds, and to processes for making such compounds. In yet another embodiment, the present invention relates to primary alcohol-terminated polyisobutylene compounds having two or more primary alcohol termini and to a process for making such compounds. In yet another embodiment, the present invention relates to primary terminated polyisobutylene compounds having two or more primary termini selected from amine groups or methacrylate groups.

First claim

What is claimed is:

1. A polyisobutylene-based polyurethane comprising the reaction product of a primary alcohol-terminated polyisobutylene having the formula

where n and m are each independently selected from an integer in the range of from 2 to about 5,000, and a diisocyanate.

2. The polyisobutylene-based polyurethane of claim 1 , wherein the diisocyanate is methylene-bis-phenyl isocyanate or 4,4′-methylene diphenyl diisocyanate.

3. The polyisobutylene-based polyurethane of claim 1 , wherein the polyisobutylene-based polyurethane does not degrade after 24 hours when exposed to concentrated HNO 3 at room temperature.

4. The polyisobutylene-based polyurethane of claim 1 , wherein the polyisobutylene-based polyurethane exhibits no percent weight loss determined gravimetrically using the expression W loss =(W b −W a /W b ) 100 when exposed to HNO 3 after 24 hours, where W loss is percent weight loss and W b and W a are the weights of the samples before and after HNO 3 exposure, respectively.

5. The polyisobutylene-based polyurethane of claim 1 , wherein the reaction product of the primary alcohol-terminated polyisobutylene and the diisocyanate further includes a chain extender.

6. The polyisobutylene-based polyurethane of claim 5 , wherein the chain extender is 1,4-butane diol.

7. A biomaterial comprising at least the polyisobutylene-based polyurethane of claim 1 .

8. A polyisobutylene based polyurethane comprising a first segment comprising a residue of a primary alcohol-terminated polyisobutylene having the formula

where n and m are each independently selected from an integer in the range of from 2 to about 5,000 and a second segment comprising a residue of a diisocyanate.

9. The polyisobutylene-based polyurethane of claim 8 , wherein the diisocyanate is selected from an aromatic diisocyanate, an aliphatic diisocyanate and combinations thereof.

10. The polyisobutylene-based polyurethane of claim 8 , wherein the diisocyanate is selected from 4,4′-methylene diphenyl diisocyanate.

11. The polyisobutylene-based polyurethane of claim 8 , wherein the end groups of at least one segment includes [—CH 2 ] n —CH 2 OH groups, wherein n=2.

12. The polyisobutylene-based polyurethane of claim 1 , wherein the polyisobutylene-based polyurethane does not degrade after 4 hours when exposed to concentrated HNO 3 at room temperature.

13. The polyisobutylene-based polyurethane of claim 1 , wherein the polyisobutylene-based polyurethane exhibits no color change after 4 hours of exposure to concentrated HNO 3 .

Assignees

• Kennedy Joseph
• Kwon Yongmoon
• Ummadisetty Subramanyam
• Univ Akron

Inventors

• Kennedy Joseph
• Kwon Yongmoon
• Ummadisetty Subramanyam

Classifications

• C08F10/10 Primary

  Isobutene · CPC title

• C08F8/00 Primary

  Chemical modification by after-treatment (graft polymers, block polymers, crosslinking with unsaturated monomers or with polymers C08F251/00 - C08F299/00; of conjugated diene rubbers C08C) · CPC title

• C08F8/32

  by reaction with amines · CPC title

• C07C211/01

  having amino groups bound to acyclic carbon atoms · CPC title

• C08F8/26

  Removing halogen atoms or halogen-containing groups from the molecule · CPC title