Isobutylene-Based Polymers with Olefinic Side Chain Substituents and Curable Compositions Containing the Same

Patent metadata

Field	Value
Publication number	US-2021024734-A1
Application number	US-201917040845-A
Country	US
Kind code	A1
Filing date	Mar 29, 2019
Priority date	Apr 3, 2018
Publication date	Jan 28, 2021
Grant date	—

Abstract

Provided herein are isobutylene-based polymer compositions comprising functionalized isobutylene-based polymer with olefinic side chain substituents, and a sulfur donor and/or accelerator cure system. The functionalized polymer is produced via nucleophilic substitution reaction in solution. The present functionalized isobutylene-based polymer compositions together with various accelerators and sulfur donors can form thermosets useful for pharmaceutical and tire applications without the use of zinc or a zinc oxide activator.

First claim

1 . An isobutylene-based polymer composition comprising:
(a) an isobutylene-based functionalized polymer; and (b) one of or a combination of any of the following:
(i) a sulfur donor;
(ii) a blend of sulfur and a sulfur donor; and
(iii) an accelerator cure system.

2 . The isobutylene-based polymer composition of claim 1 , wherein the isobutylene-based functionalized polymer is a modified poly(isobutylene-co-para-methylstyrene) amine-ionomer, wherein the amine ionomer is selected from the group consisting of 1°, 2°, and 3° amine nucleophiles with one or more pendant vinyl groups.

3 . The isobutylene-based polymer composition of claim 2 , wherein the amount of the amine ionomer present in the functionalized polymer is about 0.5 wt % to about 50 wt % based on the total weight of the functionalized polymer.

4 . The isobutylene-based polymer composition of claim 1 , wherein the isobutylene-based functionalized polymer is a modified poly(isobutylene-co-para-methylstyrene)-phosphine ionomer, wherein the phosphine ionomer is selected from diphenylphosphinostyrene, allyldiphenylphosphine, diallylphenylphosphine, diphenylvinylphosphine, triallyphosphosphine, and combinations thereof.

5 . The isobutylene-based polymer composition of claim 4 , wherein the amount of the phosphine ionomer present in the functionalized polymer is about 0.5 wt % to about 50 wt % based on the total weight of the functionalized polymer.

6 . The isobutylene-based polymer composition of claim 1 , further comprising at least one filler.

7 . The isobutylene-based polymer composition of claim 1 , wherein the sulfur donor is selected from the group consisting of tetramethyl thiuram disulfide (“TMTD”), 4,4′-dithiodimorpholine, dipentamethylene thiuram tetrasulfide (“DPTT”), and thiocarbamyl sulfonamide.

8 . The isobutylene-based polymer composition of claim 1 , wherein the accelerator cure system comprises one or more of thiazoles, amines, guanidines, sulfenamides, thiurams, dithiocarbamates, and/or zanthates.

9 . The isobutylene-based polymer composition of claim 8 , wherein the accelerator cure system is N-cyclohexyl-2-benzothiazole sulfenamide (“CBS”) or diphenylguanidine (“DPG”).

10 . The isobutylene-based polymer composition of claim 6 , wherein the filler is selected from the group of carbon black, white filler, and combinations thereof.

11 . The isobutylene-based polymer composition of claim 1 , wherein the composition is useful as a thermoset in pharmaceutical and tire applications.

12 . A thermoset composition comprising:
(a) an isobutylene-based functionalized polymer; and (b) one of or a combination of any of the following:
(i) a sulfur donor;
(ii) a blend of sulfur and a sulfur donor; and
(iii) an accelerator cure system;
wherein the composition is substantially free of zinc.

13 . The thermoset composition of claim 12 , wherein the isobutylene-based functionalized polymer is a modified poly(isobutylene-co-para-methylstyrene) amine-ionomer, wherein the amine ionomer is selected from the group consisting of 1°, 2°, and 3° amine nucleophiles with one or more pendant vinyl groups.

14 . The thermoset composition of claim 13 , wherein the amount of the amine ionomer present in the functionalized polymer is about 0.5 wt % to about 50 wt % based on the total weight of the functionalized polymer.

15 . The thermoset composition of claim 12 , wherein the isobutylene-based functionalized polymer is a modified poly(isobutylene-co-para-methylstyrene)-phosphine ionomer, wherein the phosphine ionomer is selected from diphenylphosphinostyrene, allyldiphenylphosphine, diallylphenylphosphine, diphenylvinylphosphine, triallyphosphosphine, and combinations thereof.

16 . The thermoset composition of claim 15 , wherein the amount of the phosphine ionomer present in the functionalized polymer is about 0.5 wt % to about 50 wt % based on the total weight of the functionalized polymer.

17 . The thermoset composition of claim 12 , further comprising at least one filler.

18 . The thermoset composition of claim 12 , wherein the sulfur donor is selected from the group consisting of tetramethyl thiuram disulfide (“TMTD”), 4,4′-dithiodimorpholine, dipentamethylene thiuram tetrasulfide (“DPTT”), and thiocarbamyl sulfonamide.

19 . The thermoset composition of claim 12 , wherein the accelerator cure system comprises one or more of thiazoles, amines, guanidines, sulfenamides, thiurams, dithiocarbamates, and/or zanthates.

20 . The thermoset composition of claim 19 , wherein the accelerator cure system is N-cyclohexyl-2-benzothiazole sulfenamide (“CBS”) or diphenylguanidine (“DPG”).

21 . The thermoset composition of claim 17 , wherein the filler is selected from the group of carbon black, white filler, and combinations thereof.

22 . A rubber composition comprising the thermoset composition of claim 12 .

23 . The rubber composition of claim 22 further comprising a hydrocarbon resin.

24 . An article comprising the rubber composition of claim 22 .

Assignees

• Exxonmobil Chemical Patents Inc

Inventors

• Nguyen Paul Tu Quang
• Tripathy Ranjan
• Mann Jason A
• Chen Yuan-Ju
• Blok Edward J
• Dias Anthony J
• Jangda Abdul M

Classifications

• C08F8/32

  by reaction with amines · CPC title

• C08K5/40

  Thiurams, {i.e. compounds containing[IMAGE cpc-sch-C08K-1011.gif] groups} · CPC title

• C08F8/00

  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

• C08L2312/00

  Crosslinking · CPC title

• C08K5/44

  Sulfenamides · CPC title