CA2420244A1 - Improved processability butyl rubber and process for production thereof - Google Patents
Improved processability butyl rubber and process for production thereof Download PDFInfo
- Publication number
- CA2420244A1 CA2420244A1 CA002420244A CA2420244A CA2420244A1 CA 2420244 A1 CA2420244 A1 CA 2420244A1 CA 002420244 A CA002420244 A CA 002420244A CA 2420244 A CA2420244 A CA 2420244A CA 2420244 A1 CA2420244 A1 CA 2420244A1
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- monomer
- amount
- multiolefin
- butyl polymer
- weight
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- 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
Links
- 238000000034 method Methods 0.000 title claims abstract 21
- 238000004519 manufacturing process Methods 0.000 title claims abstract 3
- 229920005549 butyl rubber Polymers 0.000 title 1
- 239000000178 monomer Substances 0.000 claims abstract 59
- 229920000642 polymer Polymers 0.000 claims abstract 37
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract 31
- 239000000203 mixture Substances 0.000 claims abstract 27
- 239000011541 reaction mixture Substances 0.000 claims abstract 15
- 239000003431 cross linking reagent Substances 0.000 claims abstract 14
- 239000012986 chain transfer agent Substances 0.000 claims abstract 13
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims abstract 12
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims abstract 10
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract 5
- 150000005673 monoalkenes Chemical class 0.000 claims 24
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-β-pinene Chemical compound C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 claims 7
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 4
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical compound CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 claims 4
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 claims 4
- RCJMVGJKROQDCB-UHFFFAOYSA-N 2-methylpenta-1,3-diene Chemical compound CC=CC(C)=C RCJMVGJKROQDCB-UHFFFAOYSA-N 0.000 claims 4
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 claims 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 4
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims 4
- 229940116441 divinylbenzene Drugs 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- APPOKADJQUIAHP-GGWOSOGESA-N (2e,4e)-hexa-2,4-diene Chemical compound C\C=C\C=C\C APPOKADJQUIAHP-GGWOSOGESA-N 0.000 claims 2
- BOGRNZQRTNVZCZ-AATRIKPKSA-N (3e)-3-methylpenta-1,3-diene Chemical compound C\C=C(/C)C=C BOGRNZQRTNVZCZ-AATRIKPKSA-N 0.000 claims 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims 2
- ZJQIXGGEADDPQB-UHFFFAOYSA-N 1,2-bis(ethenyl)-3,4-dimethylbenzene Chemical group CC1=CC=C(C=C)C(C=C)=C1C ZJQIXGGEADDPQB-UHFFFAOYSA-N 0.000 claims 2
- HIACAHMKXQESOV-UHFFFAOYSA-N 1,2-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC=C1C(C)=C HIACAHMKXQESOV-UHFFFAOYSA-N 0.000 claims 2
- BOGRNZQRTNVZCZ-UHFFFAOYSA-N 1,2-dimethyl-butadiene Natural products CC=C(C)C=C BOGRNZQRTNVZCZ-UHFFFAOYSA-N 0.000 claims 2
- JLSUFZZPRVNDIW-UHFFFAOYSA-N 1-ethenylcyclohexa-1,3-diene Chemical compound C=CC1=CC=CCC1 JLSUFZZPRVNDIW-UHFFFAOYSA-N 0.000 claims 2
- MREBNFRVGNTYOV-UHFFFAOYSA-N 1-methylcycloheptene Chemical compound CC1=CCCCCC1 MREBNFRVGNTYOV-UHFFFAOYSA-N 0.000 claims 2
- ATQUFXWBVZUTKO-UHFFFAOYSA-N 1-methylcyclopentene Chemical compound CC1=CCCC1 ATQUFXWBVZUTKO-UHFFFAOYSA-N 0.000 claims 2
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 claims 2
- XNUNYHQZMMREQD-UHFFFAOYSA-N 2-methylhepta-1,6-diene Chemical compound CC(=C)CCCC=C XNUNYHQZMMREQD-UHFFFAOYSA-N 0.000 claims 2
- DRWYRROCDFQZQF-UHFFFAOYSA-N 2-methylpenta-1,4-diene Chemical compound CC(=C)CC=C DRWYRROCDFQZQF-UHFFFAOYSA-N 0.000 claims 2
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 claims 2
- XTVRLCUJHGUXCP-UHFFFAOYSA-N 3-methyleneheptane Chemical compound CCCCC(=C)CC XTVRLCUJHGUXCP-UHFFFAOYSA-N 0.000 claims 2
- AQYKIROTAGYYQK-UHFFFAOYSA-N 5,5-dimethyl-3-methylidenehex-1-ene Chemical compound CC(C)(C)CC(=C)C=C AQYKIROTAGYYQK-UHFFFAOYSA-N 0.000 claims 2
- 150000002430 hydrocarbons Chemical class 0.000 claims 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims 2
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 claims 2
- DBSDMAPJGHBWAL-UHFFFAOYSA-N penta-1,4-dien-3-ylbenzene Chemical compound C=CC(C=C)C1=CC=CC=C1 DBSDMAPJGHBWAL-UHFFFAOYSA-N 0.000 claims 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims 2
- GQIJYUMTOUBHSH-IJIVKGSJSA-N piperyline Chemical compound C=1C=C2OCOC2=CC=1/C=C/C=C/C(=O)N1CCCC1 GQIJYUMTOUBHSH-IJIVKGSJSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- NNOAPAKAIIYKJW-UHFFFAOYSA-N 2-methylprop-1-ene 2,4,4-trimethylpent-1-ene Chemical compound CC(C)=C.CC(C)=C.CC(=C)CC(C)(C)C NNOAPAKAIIYKJW-UHFFFAOYSA-N 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 238000001125 extrusion Methods 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/04—Monomers containing three or four carbon atoms
- C08F210/08—Butenes
- C08F210/10—Isobutene
- C08F210/12—Isobutene with conjugated diolefins, e.g. butyl rubber
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
Abstract
A butyl polymer having improved processability is described, together with a process for production thereof. The butyl polymer derived from a reaction mixture which contains: (i) a monomer mixture comprising a C4 to C7 monoolef in monomer (preferably isobutylene) and a C4 to C14 multiolefin monomer (preferably isoprene); (ii) a multiolefin cross-linking agent (preferably divinyl benzene); and (iii) a chain transfer agent (preferably diisobutylene (2,4,4-trimethyl-1-pentene)). The subject butyl polymer has an improved balance of cold flow, filler dispersion, extrusion rate and die swell.</SDOA B>
Claims (44)
1. A butyl polymer having improved processability, the butyl polymer being derived from a reaction mixture comprising:
(i) a monomer mixture comprising a C4 to C7 monoolefin monomer and a C4 to C14 multiolefin monomer or .beta.-pinene;
(ii) a multiolefin cross-linking agent; and (iii) a chain transfer agent.
(i) a monomer mixture comprising a C4 to C7 monoolefin monomer and a C4 to C14 multiolefin monomer or .beta.-pinene;
(ii) a multiolefin cross-linking agent; and (iii) a chain transfer agent.
2. The butyl polymer defined in claim 1, wherein the C4 to C7 monoolefin monomer is selected from the group comprising isobutylene, 2-methyl-1-butene, 3-methyl-1-butene, 2-methyl-2-butene, 4-methyl-1-pentene and mixtures thereof.
3. The butyl polymer defined in claim 2, wherein the C4 to C7 monoolefin monomer comprises isobutylene.
4. The butyl polymer defined in any one of claims 1 to 3, wherein the C4 to C14 multiolefin monomer is selected from the group comprising isoprene, butadiene, 2-methyl-butadiene, 2,4-dimethylbutadiene, piperyline, 3-methyl-1,3-pentadiene, 2,4-hexadiene, 2-neopentylbutadiene, 2-methly-1,5-hexadiene, 2,5-dimethly-2,4-hexadiene, 2-methyl-1,4-pentadiene, 2-methyl-1,6-heptadiene, cyclopentadiene, methylcyclopentadiene, cyclohexadiene, 1-vinyl-cyclo-hexadiene and mixtures thereof.
5. The butyl polymer defined in claim 4, wherein the C4 to C14 multiolefin monomer comprises isoprene.
6. The butyl polymer defined in any one of claims 1 to 5, wherein the monomer mixture comprises from about 80%
to about 99% by weight C4 to C7 monoolefin monomer and from about 1.0% to about 20% by weight C4 to C14 multiolefin monomer or .beta.pinene.
to about 99% by weight C4 to C7 monoolefin monomer and from about 1.0% to about 20% by weight C4 to C14 multiolefin monomer or .beta.pinene.
7. The butyl polymer defined in claim 6, wherein the monomer mixture comprises from about 85% to about 99% by weight C4 to C7 monoolefin monomer and from about 1.0% to about 15% by weight C4 to C14 multiolefin monomer or .beta.-pinene.
8. The butyl polymer defined in claim 7, wherein the monomer mixture comprises from about 95% to about 99% by weight C4 to C7 monoolefin monomer and from about 1% to about 5.0% by weight C4 to C14 multiolefin monomer or .beta.-pinene.
9. The butyl polymer defined in any one of claims 1 to 8, wherein the multiolefin crosslinking agent comprises a diolefinic hydrocarbon compound.
10. The butyl polymer defined in claim 9, wherein the multiolefin crosslinking agent is selected from the group comprising divinylbenzene, diisopropenylbenzene, divinyltoluene, divinylxylene and a C1 to C20 alkyl-substituted derivatives thereof.
11. The butyl polymer defined in claim 10, wherein the multiolefin crosslinking agent comprises divinylbenzene.
12. The butyl polymer defined in any one of claims 1 to 11, wherein the multiolefin crosslinking agent is present in the reaction mixture in an amount in the range of from about 0.01 % to about 3.0 % by weight based on the amount of the C4 to C7 monoolefin monomer in the monomer mixture.
13. The butyl polymer defined claim 12, wherein the multiolefin crosslinking agent is present in the reaction mixture in an amount in the range of from about 0.05 % to about 1.0 % by weight based on the amount of the C4 to C10 monoolefin monomer in the monomer mixture.
14. The butyl polymer defined in claim 13, wherein the multiolefin crosslinking agent is present in the reaction mixture in an amount in the range of from about 0.1 % to about 0.4 % by weight based on the amount of the C4 to C7 monoolefin monomer in the monomer mixture.
15. The butyl polymer defined in any one of claims 1 to 14, wherein the chain transfer agent is selected from the group comprising piperylene, 1-methylcycloheptene, 1-methylcyclo-pentene, 2-ethyl-1-hexene, 2,4,4-trimethyl-1-pentene, indene and mixtures thereof.
16. The butyl polymer defined in claim 15, wherein the chain transfer agent comprises 2,4,4-trimethyl-1-pentene.
17. The butyl polymer defined in any one of claims 1 to 16, wherein the chain transfer agent is present in the reaction mixture in an amount in the range of from about 0.01 % to about 2.0 % by weight based on the amount of the C4 to C7 monoolefin monomer in the monomer mixture.
18. The butyl polymer defined in claim 17, wherein the chain transfer agent is present in the reaction mixture in an amount in the range of from about 0.01 % to about 1.4 % by weight based on the amount of the C4 to C7 monoolefin monomer in the monomer mixture.
19. The butyl polymer defined in claim 18, wherein the chain transfer agent is present in the reaction mixture in an amount in the range of from about 0.05 % to about 0.5 % by weight based on the amount of the C4 to C7 monoolefin monomer in the monomer mixture.
20. The butyl polymer defined in any one of claims 1 to 19, wherein the polymer comprises a halogenated butyl polymer.
21. The butyl polymer defined in claim 20, wherein the polymer is brominated.
22. The butyl polymer defined in claim 20, wherein the polymer is chlorinated.
23. The butyl polymer defined in any one of claims 20 to 22, wherein the amount of halogen is in the range of from about 0.1 to about 8% by weight of the polymer.
24. The butyl polymer defined in claim 23, wherein the amount of halogen is in the range of from about 0.5 to about 4% by weight of the polymer.
25. The butyl polymer defined in claim 24, wherein the amount of halogen is in the range of from about 1.5 to about 3% by weight of the polymer.
26. A process for preparing a butyl polymer having improved processability, the process comprising the steps of contacting a reaction mixture comprising:
a monomer mixture comprising a C4 to C7 monoolefin monomer and a C4 to C14 multiolefin monomer;
a multiolefin cross-liking agent;
a chain transfer agent; and a catalyst system.
a monomer mixture comprising a C4 to C7 monoolefin monomer and a C4 to C14 multiolefin monomer;
a multiolefin cross-liking agent;
a chain transfer agent; and a catalyst system.
27. The process defined in claim 26, wherein the C4 to C7 monoolefin monomer is selected from the group comprising isobutylene, 2-methyl-1-butene, 3-methyl-1-butene, 2-methyl-2-butene, 4-methyl-1-pentene and mixtures thereof.
28. The process defined in claim 27, wherein the C4 to C7 monoolefin monomer comprises isobutylene.
29. The process defined in any one of claims 26 to 28, wherein the C4 to C14 multiolefin monomer is selected from the group comprising isoprene, butadiene, 2-methylbutadiene, 2,4-dimethylbutadiene, piperyline, 3-methyl-1,3-pentadiene, 2,4-hexadiene, 2-neopentylbutadiene, 2-methly-1,5-hexadiene, 2,5-dimethly-2,4-hexadiene, 2-methyl-1,4-pentadiene, 2-methyl-1,6-heptadiene, cyclopentadiene, methylcyclopentadiene, cyclohexadiene, 1-vinyl-cyclo-hexadiene and mixtures thereof.
30. The process defined in claim 29, wherein the C4 to C14 multiolefin monomer comprises isoprene.
31. The process defined in any one of claims 26 to 30, wherein the monomer mixture comprises from about 80% to about 99% by weight C4 to C7 monoolefin monomer and from about 1.0% to about 20% by weight C4 to C14 multiolefin monomer or .beta.-pinene.
32. The process defined in claim 31, wherein the monomer mixture comprises from about 85% to about 99% by weight C4 to C7 monoolefin monomer and from about 1.0% to about 15%
by weight C4 to C14 multiolefin monomer or .beta.-pinene.
by weight C4 to C14 multiolefin monomer or .beta.-pinene.
33. The process defined in claim 32, wherein the monomer mixture comprises from about 95% to about 99% by weight C4 to C7 monoolefin monomer and from about 1% to about 5.0%
by weight C4 to C14 multiolefin monomer or .beta.-pinene.
by weight C4 to C14 multiolefin monomer or .beta.-pinene.
34. The process defined in any one of claims 26 to 33, wherein the multiolefin crosslinking agent comprises a diolefinic hydrocarbon compound.
35. The process defined in claim 34, wherein the multiolefin crosslinking agent is selected from the group comprising divinylbenzene, diisopropenylbenzene, divinyltoluene, divinylxylene and a C1 to C20 alkyl-substituted derivatives thereof.
36. The process defined in any one of claims 26 to 33, wherein the multiolefin crosslinking agent comprises divinyl-benzene.
37. The process defined in any one of claims 26 to 33, wherein the multiolefin crosslinking agent is present in the reaction mixture in an amount in the range of from about 0.01 % to about 3.0 % by weight based on the amount of the C4 to C7 monoolefin monomer in the monomer mixture.
38. The process defined in claim 37, wherein the multiolefin crosslinking agent is present in the reaction mixture in an amount in the range of from about 0.05 % to about 1.0 % by weight based on the amount of the C4 to C7 monoolefin monomer in the monomer mixture.
39. The process defined in claim 38, wherein the multiolefin crosslinking agent is present in the reaction mixture in an amount in the range of from about 0.1 % to about 0.4 % by weight based on the amount of the C4 to C7 monoolefin monomer in the monomer mixture.
40. The process defined in any one of claims .cndot., wherein the chain transfer agent is selected from the group comprising piperylene, 1-methylcycloheptene, 1-methylcyclopentene, 2-ethyl-1-hexene, 2,4,4-trimethyl-1-pentene, indene and mixtures thereof.
41. The process defined in any one of claims 26 to 33, wherein the chain transfer agent comprises 2,4,4-trimethyl-1-pentene.
42. The process defined in any one of claims 26 to 33, wherein the chain transfer agent is present in the reaction mixture in an amount in the range of from about 0.01 % to about 2.0 % by weight based on the amount of the C4 to C7 monoolefin monomer in the monomer mixture.
43. The process defined in claim 42, wherein the chain transfer agent is present in the reaction mixture in an amount in the range of from about 0.05 % to about 1.4 %
by weight based on the amount of the C4 to C7 monoolefin monomer in the monomer mixture.
by weight based on the amount of the C4 to C7 monoolefin monomer in the monomer mixture.
44. The process defined in claim 43, wherein the chain transfer agent is present in the reaction mixture in an amount in the range of from about 0.1 % to about 0.5 % by weight based on the amount of the C4 to C7 monoolefin monomer in the monomer mixture.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002420244A CA2420244C (en) | 2000-08-24 | 2001-08-21 | Improved processability butyl rubber and process for production thereof |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002316741A CA2316741A1 (en) | 2000-08-24 | 2000-08-24 | Improved processability butyl rubber and process for production thereof |
| CA2,316,741 | 2000-08-24 | ||
| CA002420244A CA2420244C (en) | 2000-08-24 | 2001-08-21 | Improved processability butyl rubber and process for production thereof |
| PCT/CA2001/001188 WO2002016452A1 (en) | 2000-08-24 | 2001-08-21 | Improved processability butyl rubber and process for production thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2420244A1 true CA2420244A1 (en) | 2002-02-28 |
| CA2420244C CA2420244C (en) | 2009-11-17 |
Family
ID=25682036
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002420244A Expired - Fee Related CA2420244C (en) | 2000-08-24 | 2001-08-21 | Improved processability butyl rubber and process for production thereof |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2420244C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005080452A1 (en) * | 2004-02-23 | 2005-09-01 | Lanxess Inc. | Peroxide curable rubber compound containing high-isoprene butyl rubber |
-
2001
- 2001-08-21 CA CA002420244A patent/CA2420244C/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005080452A1 (en) * | 2004-02-23 | 2005-09-01 | Lanxess Inc. | Peroxide curable rubber compound containing high-isoprene butyl rubber |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2420244C (en) | 2009-11-17 |
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|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20180821 |