Polyisobutylenes and process for making same

Patent metadata

Field	Value
Publication number	US-9359465-B2
Application number	US-201314017761-A
Country	US
Kind code	B2
Filing date	Sep 4, 2013
Priority date	Nov 30, 2006
Publication date	Jun 7, 2016
Grant date	Jun 7, 2016

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 method for producing a primary amine-terminated polyisobutylene compound comprising the steps of:
(i) providing an allyl-terminated polyisobutylene having at least two allyl termini, wherein the allyl termini are formed from straight C 3 to C 12 allyl groups having a double bond present at the end of the allyl group;
(ii) subjecting the allyl-terminated polyisobutylene to anti-Markovnikov bromination to form a primary bromine-terminated polyisobutylene compound having at least two primary bromine termini;
(iii) converting the primary bromine-terminated polyisobutylene compound to a primary phthalimide-terminated polyisobutylene via a reaction with at least one alkaline phthalimide compound, the primary phthalimide-terminated polyisobutylene having at least two primary phthalimide termini;
(iv) converting the primary phthalimide-terminated polyisobutylene compound to a primary amine-terminated compound via a reaction with an amine hydrate compound; and
(v) recovering the primary amine-terminated polyisobutylene.

2. The method of claim 1 , wherein the allyl termini are —CH 2 —CH═CH 2 .

3. The method of claim 1 , wherein the anti-Markovnikov bromination reaction of Step (ii) utilizes HBr.

4. The method of claim 1 , wherein the primary amine-terminated polyisobutylene compound is a linear molecule.

5. The method of claim 1 , wherein the primary amine-terminated polyisobutylene compound is a star molecule.

6. The method of claim 1 , wherein the primary amine-terminated polyisobutylene compound is a hyperbranched molecule.

7. The method of claim 1 , wherein the primary amine-terminated polyisobutylene compound is an arborescent molecule.

8. The method of claim 1 , wherein Step (iv) comprises the use of hydrazine hydrate.

Assignees

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

Inventors

• Kennedy Joseph P
• Kwon Yongmoon
• Ummadisetty Subramanyam

Classifications

• C08F2810/40

  taking place solely at one end or both ends of the polymer backbone, i.e. not in the side or lateral chains · CPC title

• C07C19/075

  containing bromine · CPC title

• C08F110/10

  Isobutene · CPC title

• 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