CA2282900A1 - Halogenated terpolymers of isobutylene, diolefin monomer and styrenic monomer - Google Patents

Halogenated terpolymers of isobutylene, diolefin monomer and styrenic monomer Download PDF

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Publication number
CA2282900A1
CA2282900A1 CA002282900A CA2282900A CA2282900A1 CA 2282900 A1 CA2282900 A1 CA 2282900A1 CA 002282900 A CA002282900 A CA 002282900A CA 2282900 A CA2282900 A CA 2282900A CA 2282900 A1 CA2282900 A1 CA 2282900A1
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CA
Canada
Prior art keywords
monomer
weight
halogenated butyl
polymer
butyl polymer
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002282900A
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French (fr)
Other versions
CA2282900C (en
Inventor
Gabor Kaszas
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Arlanxeo Canada Inc
Original Assignee
Bayer Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to CA2282900A priority Critical patent/CA2282900C/en
Application filed by Bayer Inc filed Critical Bayer Inc
Priority to AU72629/00A priority patent/AU7262900A/en
Priority to BRPI0017502-1A priority patent/BR0017502B1/en
Priority to RU2002110664/04A priority patent/RU2002110664A/en
Priority to BR0014125-9A priority patent/BR0014125A/en
Priority to CNB00813135XA priority patent/CN1159351C/en
Priority to JP2001525244A priority patent/JP2003510380A/en
Priority to EP00960245.9A priority patent/EP1228106B1/en
Priority to PCT/CA2000/001044 priority patent/WO2001021672A1/en
Priority to TW089119287A priority patent/TW591042B/en
Publication of CA2282900A1 publication Critical patent/CA2282900A1/en
Priority to US10/390,113 priority patent/US6960632B2/en
Priority to HK03102633A priority patent/HK1050539A1/en
Priority to US11/208,320 priority patent/US7402633B2/en
Priority to US12/156,501 priority patent/US20090018297A1/en
Priority to US12/146,078 priority patent/US7868100B2/en
Application granted granted Critical
Publication of CA2282900C publication Critical patent/CA2282900C/en
Priority to JP2012000222A priority patent/JP5450671B2/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/18—Introducing halogen atoms or halogen-containing groups
    • C08F8/20—Halogenation

Abstract

A halogenated butyl polymer having improved properties, the butyl polymer derived from a monomer mixture comprising a C4 to C8 monoolefin monomer, a C4 to C14 multiolefin monomer and a styrenic monomer with a catalyst system to produce the butyl polymer. The improved properties include faster cure, higher maximum torque, higher delta torque, relatively stable modulus over time, improved hot air aging properties and improved aged flexure properties. These improved properties are believed to result from direct interaction between the styrenic moieties in the polymer backbone with a crosslinking agent added to vulcanize the halogenated butyl rubber.

Claims (30)

1. A halogenated butyl polymer having improved curing and/or aging properties, the butyl polymer derived from a monomer mixture comprising a C4 to C8 monoolefin monomer, a C4 to C14 multiolefin monomer and a styrenic monomer with a catalyst system to produce the butyl polymer.
2. The halogenated butyl polymer defined in claim 1, wherein the C4 to C8 monoolefin monomer may be selected from the group comprising isobutylene, 2-methylpropene-1, 3-methylbutene-1,4, methylpentene-1,2, methylpentene-1,4, ethylbutene-1, 4-ethylpentene-1 and mixtures thereof.
3. The halogenated butyl polymer defined in claim 1, wherein the C4 to C8 monoolefin monomer comprises isobutylene.
4. The halogenated butyl polymer defined in any one of claims 1-3, wherein the to C14 multiolefin monomer is selected from the group comprising isoprene, butadiene-1,3, 2,4-dimethylbutadiene-1,3, piperyline, 3-methylpentadiene-1,3, hexadiene-2,4, 2-neopentylbutadiene-1,3, 2-methlyhexadiene-1,5, 2,5-dimethlyhexadiene-2,4, 2-methylpentadiene-1,4, 2-methylheptadiene-1,6, cyclopentadiene, methylcyclopentadiene, cyclohexadiene, 1-vinyl-cyclohexadiene and mixtures thereof.
5. The halogenated butyl polymer defined in any one of claims 1-3, wherein the to C14 multiolefin monomer comprises isoprene.
6. The halogenated butyl polymer defined in any one of claims 1-5, wherein the styrenic monomer is selected from the group comprising p-methylstyrene, styrene, .alpha.-methylstyrene, p-chlorostyrene, p-methoxystyrene and mixtures thereof.
7. The halogenated butyl polymer defined in any one of claims 1-5, wherein the styrenic monomer comprises a member selected from the group comprising styrene, p-methylstyrene and mixtures thereof.
8. The halogenated butyl polymer defined in any one of claims 1-7, wherein the monomer mixture comprises from about 80% to about 99% by weight C4 to C8 monoolefin monomer, from about 0.5% to about 5% by weight C4 to C14 multiolefin monomer and from about 0.5% to about 15% by weight styrenic monomer.
9. The halogenated butyl polymer defined in any one of claims 1-7, wherein the monomer mixture comprises from about 85% to about 99% by weight C4 to C8 monoolefin monomer, from about 0.5% to about 5% by weight C4 to C14 multiolefin monomer and from about 0.5% to about 10% by weight styrenic monomer.
10. The halogenated butyl polymer defined in any one of claims 1-7, wherein the monomer mixture comprises from about 87% to about 94% by weight C4 to C8 monoolefin monomer, from about 1% to about 3% by weight C4 to C14 multiolefin monomer and from about 5% to about 10% by weight styrenic monomer.
11. The halogenated butyl polymer defined in any one of claims 1-10, wherein the polymer is brominated.
12. The halogenated butyl polymer defined in any one of claims 1-10, wherein the polymer is chlorinated.
13. The halogenated butyl polymer defined in any one of claims 1-12, wherein the amount of halogen is in the range of from about 0.1 to about 8% by weight of the polymer.
14. The halogenated butyl polymer defined in any one of claims 1-12, wherein the amount of halogen is in the range of from about 0.5 to about 4% by weight of the polymer.
15. The halogenated butyl polymer defined in any one of claims 1-12, wherein the amount of halogen is in the range of from about 1.5 to about 3% by weight of the polymer.
16. A process for preparing a halogenated butyl polymer having improved curing and/or aging properties, the process comprising the steps of:
contacting a monomer mixture comprising a C4 to C8 monoolefin monomer, a C4 to C14 multiolefin monomer and a styrenic monomer with a catalyst system to produce a terpolymer; and halogenating the terpolymer to produce the halogenated butyl polymer.
17. The process defined in claim 16, wherein the C4 to C8 monoolefin monomer may be selected from the group comprising isobutylene, 2-methylpropene-1,3-methylbutene-1,4,methylpentene-1,2,methylpentene-1,4,ethylbutene-1,4-ethylpentene-1,beta-pinene and mixtures thereof.
18. The process defined in claim 16, wherein the C4 to C8 monoolefin monomer comprises isobutylene.
19. The process defined in any one of claims 16-18, wherein the C4 to C14 multiolefin monomer is selected from the group comprising isoprene, butadiene-1,3, 2,4-dimethylbutadiene-1,3, piperyline, 3-methylpentadiene-1,3, hexadiene-2,4, neopentylbutadiene-1,3, 2-methlyhexadiene-1,5, 2,5-dimethlyhexadiene-2,4, 2-methylpentadiene-1,4, 2-methylheptadiene-1,6, cyclopentadiene, methylcyclopentadiene, cyclohexadiene, 1-vinyl-cyclohexadiene and mixtures thereof.
20. The process defined in any one of claims 16-18, wherein the C4 to C14 multiolefin monomer comprises isoprene.
21. The process defined in any one of claims 16-20, wherein the styrenic monomer is selected from the group comprising p-methylstyrene, styrene, .alpha.-methylstyrene, p-chlorostyrene, p-methoxystyrene and mixtures thereof.
22. The process defined in any one of claims 16-20, wherein the styrenic monomer comprises a member selected from the group comprising styrene, p-methylstyrene and mixtures thereof.
23. The process defined in any one of claims 16-22, wherein the monomer mixture comprises from about 80% to about 99% by weight C4 to C8 monoolefin monomer, from about 0.5% to about 5% by weight C4 to C14 multiolefin monomer and from about 0.5%
to about 15% by weight styrenic monomer.
24. The process defined in any one of claims 16-22, wherein the monomer mixture comprises from about 85% to about 99% by weight C4 to C8 monoolefin monomer, from about 0.5% to about 5% by weight C4 to C14 multiolefin monomer and from about 0.5%
to about 10% by weight styrenic monomer.
25. The process defined in any one of claims 16-22, wherein the monomer mixture comprises from about 87% to about 94% by weight C4 to C8 monoolefin monomer, from about 1% to about 3% by weight C4 to C14 multiolefin monomer and from about 5%
to about 10% by weight styrenic monomer.
26. The process defined in any one of claims 16-25, wherein the halogenating agent comprises bromine.
27. The process defined in any one of claims 16-25, wherein the halogenating agent comprises chlorine.
28. The process defined in any one of claims 16-27, wherein the halogenating agent is used in an amount to provide a residual halogen content in the range of from about 0.1 to about 8% by weight of the polymer.
29. The process defined in any one of claims 16-27, wherein the halogenating agent is used in an amount to provide a residual halogen content in the range of from about 0.5 to about 4% by weight of the polymer.
30. The process defined in any one of claims 16-27, wherein the halogenating agent is used in an amount to provide a residual halogen content in the range of from about 1.5 to about 3% by weight of the polymer.
CA2282900A 1999-09-20 1999-09-20 Halogenated terpolymers of isobutylene, diolefin monomer and styrenic monomer Expired - Lifetime CA2282900C (en)

Priority Applications (16)

Application Number Priority Date Filing Date Title
CA2282900A CA2282900C (en) 1999-09-20 1999-09-20 Halogenated terpolymers of isobutylene, diolefin monomer and styrenic monomer
BRPI0017502-1A BR0017502B1 (en) 1999-09-20 2000-09-19 halogenated butyl terpolymer comprising a c4-c8 monoolefin monomer, a c4 to c14 multiolefin monomer and p-methylstyrene.
RU2002110664/04A RU2002110664A (en) 1999-09-20 2000-09-19 HALOGENED Ternary Copolymers of Isobutylene, Diolefin Monomer and Styrene Monomer
BR0014125-9A BR0014125A (en) 1999-09-20 2000-09-19 Halogenated terpolymers of isobutylene, diolefin monomer and styrenic monomer
CNB00813135XA CN1159351C (en) 1999-09-20 2000-09-19 Halogenated terpolymers of isobutylene, diolefin monomer and styrenic monomer
JP2001525244A JP2003510380A (en) 1999-09-20 2000-09-19 Halogenated terpolymer of isobutylene, diolefin monomer and styrene monomer
EP00960245.9A EP1228106B1 (en) 1999-09-20 2000-09-19 Halogenated terpolymers of isobutylene, diolefin monomer and styrenic monomer
PCT/CA2000/001044 WO2001021672A1 (en) 1999-09-20 2000-09-19 Halogenated terpolymers of isobutylene, diolefin monomer and styrenic monomer
AU72629/00A AU7262900A (en) 1999-09-20 2000-09-19 Halogenated terpolymers of isobutylene, diolefin monomer and styrenic monomer
TW089119287A TW591042B (en) 1999-09-20 2000-09-20 A halogenated butyl polymer and the process for preparing the same
US10/390,113 US6960632B2 (en) 1999-09-20 2003-03-17 Halogenated terpolymers of isobutylene, diolefin monomer and styrenic monomer
HK03102633A HK1050539A1 (en) 1999-09-20 2003-04-10 Halogenated terpolymers of isobutylene, diolefin monomer and styrenic monomer.
US11/208,320 US7402633B2 (en) 1999-09-20 2005-08-19 Halogenated terpolymers of isobutylene, diolefin monomer and styrenic monomer
US12/156,501 US20090018297A1 (en) 1999-09-20 2008-06-03 Halogenated terpolymers of isobutylene, diolefin monomer and styrenic monomer
US12/146,078 US7868100B2 (en) 1999-09-20 2008-06-25 Halogenated terpolymers of isobutylene, diolefin monomer and styrenic monomer
JP2012000222A JP5450671B2 (en) 1999-09-20 2012-01-04 Halogenated terpolymers of isobutylene, diolefin monomers and styrenic monomers

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CA2282900A CA2282900C (en) 1999-09-20 1999-09-20 Halogenated terpolymers of isobutylene, diolefin monomer and styrenic monomer

Publications (2)

Publication Number Publication Date
CA2282900A1 true CA2282900A1 (en) 2001-03-20
CA2282900C CA2282900C (en) 2011-02-01

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CA2282900A Expired - Lifetime CA2282900C (en) 1999-09-20 1999-09-20 Halogenated terpolymers of isobutylene, diolefin monomer and styrenic monomer

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US (4) US6960632B2 (en)
EP (1) EP1228106B1 (en)
JP (2) JP2003510380A (en)
CN (1) CN1159351C (en)
AU (1) AU7262900A (en)
BR (2) BR0014125A (en)
CA (1) CA2282900C (en)
HK (1) HK1050539A1 (en)
RU (1) RU2002110664A (en)
TW (1) TW591042B (en)
WO (1) WO2001021672A1 (en)

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Publication number Publication date
BR0017502B1 (en) 2013-03-05
EP1228106B1 (en) 2016-03-16
BR0014125A (en) 2002-05-14
CN1374972A (en) 2002-10-16
HK1050539A1 (en) 2003-06-27
US20060116484A1 (en) 2006-06-01
JP5450671B2 (en) 2014-03-26
CA2282900C (en) 2011-02-01
US7868100B2 (en) 2011-01-11
RU2002110664A (en) 2003-11-20
CN1159351C (en) 2004-07-28
TW591042B (en) 2004-06-11
US20080275190A1 (en) 2008-11-06
US20090018297A1 (en) 2009-01-15
EP1228106A1 (en) 2002-08-07
WO2001021672A1 (en) 2001-03-29
JP2012062492A (en) 2012-03-29
US7402633B2 (en) 2008-07-22
US20030220454A1 (en) 2003-11-27
AU7262900A (en) 2001-04-24
JP2003510380A (en) 2003-03-18
US6960632B2 (en) 2005-11-01

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