IP Library Granted Patent US 9,856,335
Granted Patent B2
US 9,856,335 · App. 15/238,092 · Granted Jan 2, 2018

Production of highly reactive low molecular weight PIB oligomers

Inventors: Sohel K. Shaikh (Dhahran, SA); Rex Lawson (Pearland, TX)
Assignee: TPC GROUP LLC
C08F110/10C07C2/20C08K5/13C07C2527/1213
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Quick Facts
Patent No.
US 9,856,335
App. No.
15/238,092
Granted
Jan 2, 2018
Kind
B2
Abstract

In one preferred embodiment, the present invention provides a process for the liquid phase polymerization of isobutylene to manufacture highly reactive PIB oligomers having Mn under 1000, using a catalyst composition comprising a Friedel-Crafts catalyst a complexing agent, a chain transfer agent and a polymerization-retarding agent. A chain transfer agent may be selected from: α-DIB and β-DIB and mixtures thereof. A polymerization-retarding agent may be selected from:

Claims (20)

1. A polyisobutylene composition having Mn under 1000 exhibiting a multimodal molecular weight distribution, at least 70% terminal double bonds and a polydispersity under 2.0 prepared using an olefinic chain transfer agent having a molecular weight, Mn, lower than that of said composition, wherein said composition is characterized in that the composition exhibits a low molecular weight relative maximum in its molecular weight distribution corresponding to the presence of said chain transfer agent.

2. The composition according to claim 1 , wherein said chain transfer agent has a molecular weight, Mn, of from 100 to 150 Daltons.

3. The composition according to claim 1 , wherein the polyisobutylene composition has a molecular weight, Mn, of less than 800 Daltons.

4. The composition according to claim 3 , wherein the polyisobutylene composition has a molecular weight, Mn, of from 300 to less than 800 Daltons.

5. The composition according to claim 1 , wherein the polyisobutylene composition has a molecular weight, Mn, of from 300 to 1000 Daltons.

6. The composition of claim 1 , characterized in that the composition exhibits a low molecular weight relative maximum in its molecular weight distribution corresponding to the presence of said chain transfer agent at a content of from 2 weight percent to 20 weight percent.

7. The composition of claim 1 , characterized in that the composition exhibits a low molecular weight relative maximum in its molecular weight distribution corresponding to the presence of said chain transfer agent at a content of from 4 weight percent to 10 weight percent of the composition.

8. The composition of claim 1 , wherein the polydispersity of said composition is no more than about 1.65.

9. The composition of claim 1 , wherein the polydispersity of said composition is from 1.1 to 1.5.

10. A reactive low molecular weight polyisobutylene composition comprising at least 50 mol percent alpha vinylidene terminated polyisobutylene molecules, the composition having a number average molecular weight of no more than 1000 Daltons and is characterized in that the composition exhibits a low molecular weight maximum in its molecular weight distribution corresponding to the presence of an olefinic chain transfer agent.

11. The reactive low molecular weight polyisobutylene composition according to claim 10 , comprising at least 60 mol percent alpha vinylidene terminated polyisobutylene molecules.

12. The reactive low molecular weight polyisobutylene composition according to claim 10 , comprising at least 70 mol percent alpha vinylidene terminated polyisobutylene molecules.

13. The reactive low molecular weight polyisobutylene composition according to claim 10 , comprising from 50 to 99 mol percent alpha vinylidene terminated polyisobutylene molecules.

14. The reactive low molecular weight polyisobutylene composition according to claim 10 , wherein no more than 10 mole % of the PIB molecules of the composition have tetra-substituted double bonds.

15. A reactive low molecular weight polyisobutylene composition comprising at least 50 mol percent alpha vinylidene terminated polyisobutylene molecules, the composition having a number average molecular weight of no more than 1000 Daltons, wherein the composition further includes a polymerization-retarding agent and is characterized in that the composition exhibits a low molecular weight maximum in its molecular weight distribution corresponding to the presence of an olefinic chain transfer agent.

16. The reactive low molecular weight polyisobutylene composition according to claim 15 , wherein the polymerization-retarding agent comprises a phenolic compound.

17. The composition according to claim 15 , wherein said chain transfer agent has a molecular weight, Mn, of from 100 to 150 Daltons.

18. The composition according to claim 15 , wherein the polyisobutylene composition has a molecular weight, Mn, of less than 800 Daltons.

19. The composition according to claim 15 , wherein the polyisobutylene composition has a molecular weight, Mn, of from 300 to less than 800 Daltons.

20. The composition according to claim 15 , wherein the polyisobutylene composition has a molecular weight, Mn, of from 300 to 1000 Daltons.

Assignments (14)
RELEASE OF SECURITY INTEREST Recorded Dec 16, 2024
From: GLAS TRUST COMPANY LLC
To: TPC GROUP LLC
Reel/Frame 069602/0182 →
SECURITY INTEREST Recorded Dec 16, 2024
From: TPC GROUP LLC
To: JEFFERIES FINANCE LLC, AS AGENT
Reel/Frame 069594/0055 →
TERMINATION AND RELEASE OF GRANT OF SECURITY INTEREST IN UNITED STATES PATENTS AT REEL/FRAME 060287/0820 Recorded Dec 20, 2022
From: GLAS AMERICAS LLC, AS COLLATERAL AGENT
To: TPC GROUP LLC
Reel/Frame 062171/0674 →
TERMINATION AND RELEASE OF SUPPLEMENTAL GRANT OF SECURITY INTEREST IN UNITED STATES PATENTS AT REEL/FRAME 055119/0158 Recorded Dec 20, 2022
From: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS SUCCESSOR COLLATERAL AGENT TO U.S. BANK NATIONAL ASSOCIATION
To: TPC GROUP LLC
Reel/Frame 062171/0666 →
TERMINATION AND RELEASE OF SUPPLEMENTAL GRANT OF SECURITY INTEREST IN UNITED STATES PATENTS AT REEL/FRAME 049949/0024 Recorded Dec 20, 2022
From: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS SUCCESSOR COLLATERAL AGENT TO U.S. BANK NATIONAL ASSOCIATION
To: TPC GROUP LLC
Reel/Frame 062171/0658 →
RELEASE OF SECURITY INTEREST AT REEL/FRAME 60113/0169 Recorded Dec 16, 2022
From: ECLIPSE BUSINESS CAPITAL LLC, AS AGENT
To: TPC GROUP LLC
Reel/Frame 062142/0523 →
SECURITY INTEREST Recorded Dec 16, 2022
From: TPC GROUP LLC
To: ECLIPSE BUSINESS CAPITAL LLC, AS COLLATERAL AGENT
Reel/Frame 062130/0001 →
SECURITY INTEREST Recorded Dec 16, 2022
From: TPC GROUP LLC
To: GLAS TRUST COMPANY LLC, AS COLLATERAL AGENT
Reel/Frame 062130/0137 →
RELEASE OF SECURITY INTEREST AT REEL/FRAME 49942/0467 Recorded Jun 8, 2022
From: BANK OF AMERICA, N.A., AS AGENT
To: TPC GROUP LLC
Reel/Frame 060392/0673 →
GRANT OF SECURITY INTEREST IN UNITED STATES PATENTS Recorded Jun 6, 2022
From: TPC GROUP LLC
To: GLAS AMERICAS LLC, AS COLLATERAL AGENT
Reel/Frame 060287/0820 →
SECURITY INTEREST Recorded Jun 6, 2022
From: TPC GROUP LLC
To: ECLIPSE BUSINESS CAPITAL LLC, AS AGENT
Reel/Frame 060113/0169 →
SECURITY INTEREST Recorded Feb 2, 2021
From: TPC GROUP LLC
To: U.S. BANK NATIONAL ASSOCIATION, AS AGENT
Reel/Frame 055119/0158 →
SECURITY INTEREST Recorded Aug 2, 2019
From: TPC GROUP LLC
To: BANK OF AMERICA, N.A.
Reel/Frame 049942/0467 →
SECURITY AGREEMENT Recorded Aug 2, 2019
From: TPC GROUP LLC
To: U.S. BANK NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 049949/0024 →
Continuity (4)
Division 14118254
Provisional Application 61586206 · Jan 13, 2012
Provisional Application 61520328 · Jun 8, 2011
Related Publication 20160355620A1 · Dec 8, 2016