WO2005080452A1 - Compose de caoutchouc durcissable en peroxyde contenant du caoutchouc presentant une teneur elevee en isoprene butyle - Google Patents

Compose de caoutchouc durcissable en peroxyde contenant du caoutchouc presentant une teneur elevee en isoprene butyle Download PDF

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Publication number
WO2005080452A1
WO2005080452A1 PCT/CA2005/000254 CA2005000254W WO2005080452A1 WO 2005080452 A1 WO2005080452 A1 WO 2005080452A1 CA 2005000254 W CA2005000254 W CA 2005000254W WO 2005080452 A1 WO2005080452 A1 WO 2005080452A1
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Prior art keywords
mol
multiolefin
repeating units
units derived
monomer
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PCT/CA2005/000254
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English (en)
Inventor
Rui Resendes
Adam Gronowski
Shunji Baba
Yong Siak Seow
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Lanxess Inc.
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Publication of WO2005080452A1 publication Critical patent/WO2005080452A1/fr

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    • 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
    • C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
    • C08F236/08—Isoprene
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0025—Crosslinking or vulcanising agents; including accelerators

Definitions

  • the present invention relates to a peroxide curable rubber compound containing polymers with a Mooney viscosity of at least 25 Mooney-units and a gel content of less than 15 wt.% comprising repeating units derived from at least one isoolefm monomer, more than 4.1 mol% of repeating units derived from at least one multiolefin monomer, as well as optionally further copolymerizable monomers, and repeating units derived from at least one multiolefin cross-linking agent containing no transition metal compounds and no organic nitro compounds.
  • the polymers have a multiolefin content of greater than 4.1 mol%, and a gel content of less than 10 wt.% and have been produced at conversions ranging from 70 % to 95%.
  • the polymers have a Mooney viscosity in the range of from 25-70 MU, more preferably 30-60 MU, even more preferably 30-55 MU.
  • Butyl rubber is understood to be a copolymer of an isoolefm and one or more, preferably conjugated, multiolefms as comonomers.
  • Commercial butyl comprise a major portion of isoolefm and a minor amount, not more than 2.5 mol %, of a conjugated multiolefin.
  • the preferred isoolefm is isobutylene.
  • this invention also covers polymers optionally comprising additional copolymerizable co-monomers.
  • Butyl rubber or butyl polymer is generally prepared in a slurry process using methyl chloride as a vehicle and a Friedel-Crafts catalyst as part of the polymerization initiator. The methyl chloride offers the advantage that A1C1 , a relatively inexpensive
  • Friedel-Crafts catalyst is soluble in it, as are the isobutylene and isoprene comonomers. Additionally, the butyl rubber polymer is insoluble in the methyl chloride and precipitates out of solution as fine particles.
  • the polymerization is generally carried out at temperatures of about -90°C to -100°C. See U.S. Patent No. 2,356,128 and Ullmanns Encyclopedia of Industrial Chemistry, volume A 23, 1993, pages 288-295. The low polymerization temperatures are required in order to achieve molecular weights which are sufficiently high for rubber applications.
  • Peroxide curable butyl rubber compounds offer several advantages over conventional, sulfur-curing, systems.
  • peroxide-curable formulations are considered to be "clean" in that they do not contain any extractable inorganic impurities (e.g. sulfur).
  • the clean rubber articles can therefore be used, for example, in condenser caps, biomedical devices, pharmaceutical devices (stoppers in medicine-containing vials, plungers in syringes) and possibly in seals for fuel cells. It is well accepted that polyisobutylene and butyl rubber decompose under the action of organic peroxides.
  • an electron-withdrawing group-containing polyfunctional monomer ethylene dimethacrylate, trimethylolpropane triacrylate, ⁇ , ⁇ '- -phenylene dimaleimide
  • ethylene dimethacrylate, trimethylolpropane triacrylate, ⁇ , ⁇ '- -phenylene dimaleimide can also be used (see JP-A- 172547/1994).
  • Co-Pending application CA-2,418,884 discloses a continuos process for producing polymers having a Mooney viscosity of at least 25 Mooney-units and a gel content of less than 15 wt. % comprising repeating units derived from at least one isoolefm monomer, more than 4.1 mol % of repeating units derived from at least one multiolefin monomer and optionally further copolymerizable monomers in the presence of A1C1 3 and a proton source and/or cationogen capable of initiating the polymerization process and at least one multiolefin cross-linking agent wherein the process is conducted in the absence of transition metal compounds.
  • These polymers are well suited for the inventive rubber formulations of this invention and with regards to jurisdictions allowing for this method are enclosed by reference herein.
  • the present invention provides a peroxide curable rubber compound containing polymers with a Mooney viscosity of at least 25 Mooney-units and a gel content of less than 15 wt.% comprising repeating units derived from at least one isoolefm monomer, more than 4.1 mol% of repeating units derived from at least one multiolefin monomer, as well as optionally further copolymerizable monomers, and repeating units derived from at least one multiolefin cross-linking agent containing no transition metal compounds and no organic nitro compounds.
  • the Mooney viscosity of the polymer is determined using ASTM test D1646 using a large rotor at 125 °C, a preheat phase of 1 min, and an analysis phase of 8 min (ML1+8 @ 125 °C)
  • the invention is not limited to a special isoolefm.
  • isoolefms within the range of from 4 to 16 carbon atoms, in particular 4-7 carbon atoms, such as isobutene, 2-methyl-l-butene, 3 -methyl- 1-butene, 2-methyl-2-butene, 4-methyl-l- pentene and mixtures thereof are preferred. Most preferred is isobutene.
  • the invention is not limited to a special multiolefin. Every multiolefin copolymerizable with the isoolefm known by the skilled in the art can be used. However, multiolefms within the range of from 4-14 carbon atoms, such as isoprene, butadiene, 2-methylbutadiene, 2,4-dimethylbutadiene, piperyline, 3 -methyl- 1,3- pentadiene, 2,4-hexadiene, 2-neopentylbutadiene, 2-methyl-l,5-hexadiene, 2,5- dimethyl-2,4-hexadiene, 2-methyl-l,4-pentadiene, 2-methyl-l,6-heptadiene, cyclopentadiene, methylcyclopentadiene, cyclohexadiene, 1-vinyl-cyclohexadiene and mixtures thereof, in particular conjugated dienes, are preferably used.
  • Isoprene is particularly preferably used.
  • ⁇ -pinene can also be used as a co-monomer for the isoolefm.
  • monomers every monomer copolymerizable with the isoolefms and/or dienes known by the skilled in the art can be used, ⁇ -methyl styrene, jj-methyl styrene, chlorostyrene, cyclopentadiene and methylcyclopentadiene are preferably used.
  • the multiolefin content is at least greater than 4.1 mol%, more preferably greater than 5.0 mol%, even more preferably greater than 6.0 mol%, yet even more preferably greater than 7.0 mol%.
  • the monomer mixture comprises in the range of from 80% to 95% by weight of at least one isoolefm monomer and in the range of from 4.0% to 20% by weight of at least one multiolefin monomer including ⁇ -pinene and in the range of from 0.01% to 1%) by weight of at least one multiolefin cross-linking agent.
  • the monomer mixture comprises in the range of from 83%> to 94%> by weight of at least one isoolefm monomer and in the range of from 5.0%> to 17% by weight of a multiolefin monomer or ⁇ -pinene and in the range of from 0.01%) to 1% by weight of at least one multiolefin cross-linking agent.
  • the monomer mixture comprises in the range of from 85% to 93 % by weight of at least one isoolefm monomer and in the range of from 6.0% to 15%> by weight of at least one multiolefin monomer, including ⁇ -pinene and in the range of from 0.01% to 1% by weight of at least one multiolefin cross-linking agent.
  • the weight average molecular weight, M w is preferably greater than 240 kg/mol, more preferably greater than 300 kg/mol, even more preferably greater than 500 kg/mol, yet even more preferably greater than 600 kg/mol.
  • gel is understood to denote a fraction of the polymer insoluble for 60 min in cyclohexane boiling under reflux.
  • the gel content is preferably less than 10 wt.%, more preferably less than 5 wt%>, even more preferably less than 3 wt%, yet even more preferably less than 1 wt%.
  • the butyl polymer further comprises unites derived from one or more multiolefin cross-linking agents.
  • cross-linking agent is known to those skilled in the art and is understood to denote a compound that causes chemical cross-linking between the polymer chains in opposition to a monomer that will add to the chain. Some easy preliminary tests will reveal if a compound will act as a monomer or a cross- linking agent.
  • the choice of the cross-linking agent is not particularly restricted.
  • the cross-linking comprises a multiolefinic hydrocarbon compound.
  • the multiolefin crosslinking agent is divinylbenzene, diisopropenylbenzene, divinyltoluene, divinyl-xylene and Ci to C 20 alkyl substituted derivatives thereof, and or mixtures of the compounds given.
  • the multiolefin crosslinking agent comprises divinylbenzene and diisopropenylbenzene.
  • the polymerization preferably is performed in a continuous process in slurry (suspension), in a suitable diluent, such as chloroalkanes as described in US 5,417,930.
  • the monomers are generally polymerized cationically, preferably at temperatures in the range from -120°C to +20°C, preferably in the range from -100°C to -20°C, and pressures in the range from 0.1 to 4 bar.
  • the use of a continuous reactor as opposed to a batch reactor seems to have a positive effect on the polymer.
  • the process is conducted in at least one continuos reactor having a volume of between 0.1 m and 100 m , more preferable between 1 m and 10 m .
  • Inert solvents or diluents known to the person skilled in the art for butyl polymerization may be considered as the solvents or diluents (reaction medium). These comprise alkanes, chloroalkanes, cycloalkanes or aromatics, which are frequently also mono- or polysubstituted with halogens. Hexane/chloroalkane mixtures, methyl chloride, dicl loromethane or the mixtures thereof may be mentioned in particular.
  • Chloroalkanes are preferably used in the process according to the present invention.
  • Said polymers with a Mooney viscosity of at least 25 Mooney-units and a gel content of less than 15 wt.% comprising repeating units derived from at least one isoolefm monomer, more than 4.1 mol% of repeating units derived from at least one multiolefin monomer, as well as optionally further copolymerizable monomers, and repeating units derived from at least one multiolefin cross-linking agent containing no transition metal compounds and no organic nitro compounds may be partially or fully chlorinated or brominated.
  • Bromination or chlorination can be performed according to the procedures described in Rubber Technology, 3 r Ed., Edited by Maurice Morton, Kluwer Academic Publishers, pp. 297 - 300 and references cited within this reference.
  • the rubber compounds presented in this invention are ideally suitable for the production of moldings of all kinds, in particular tyre components and industrial rubber articles, such as bungs, damping elements, profiles, films, coatings.
  • the polymers are used to this end in pure form or as a mixture with other rubbers, such as NR, BR, HNBR, NBR, SBR, EPDM or fluororubbers.
  • the preparation of these compounds is known to those skilled in the art. In most cases carbon black is added as filler and a peroxide based curing system is used.
  • organic peroxides such as dialkylperoxides, ketalperoxides, aralkylperoxides, peroxide ethers, peroxide esters, such as di-tert.-butylperoxide, bis-(tert.-butylperoxyisopropyl)-benzol, dicumylperoxide, 2,5 -dimethyl-2, 5 -di(tert.
  • BR polybutadiene
  • ABR butadiene/acrylic acid-C ⁇ -C4- alkylester-copolymers
  • CR polychloroprene
  • IR polyisoprene
  • polystyrene/butadiene-copolymers with styrene contents in the range of 1 to 60 wt%
  • NBR butadiene/acrylonitrile-copolymers with acrylonitrile contents of 5 to 60 wt%
  • HNBR partially or totally hydrogenated NBR-rubber
  • EPDM ethylene/propylene/diene- copolymers
  • FKM fluoropolymers or fluororubbers
  • the rubber composition according to the invention can contain further auxiliary products for rubbers, such as reaction accelerators, vulcanizing accelerators, vulcanizing acceleration auxiliaries, antioxidants, foaming agents, anti-aging agents, heat stabilizers, light stabilizers, ozone stabilizers, processing aids, plasticizers, tackifiers, blowing agents, dyestuffs, pigments, waxes, extenders, organic acids, inhibitors, metal oxides, and activators such as triethanolamine, polyethylene glycol, hexanetriol, etc., which are known to the rubber industry.
  • the rubber aids are used in conventional amounts, which depend inter alia on the intended use. Conventional amounts are e.g. from 0.1 to 50 wt.%>, based on rubber.
  • the composition furthermore comprises in the range of 0.1 to 20 phr of an organic fatty acid, preferably a unsaturated fatty acid having one, two or more carbon double bonds in the molecule which more preferably includes 10% by weight or more of a conjugated diene acid having at least one conjugated carbon-carbon double bond in its molecule.
  • organic fatty acid preferably a unsaturated fatty acid having one, two or more carbon double bonds in the molecule which more preferably includes 10% by weight or more of a conjugated diene acid having at least one conjugated carbon-carbon double bond in its molecule.
  • those fatty acids have in the range of from 8- 22 carbon atoms, more preferably 12-18. Examples include stearic acid, palmic acid and oleic acid and their calcium-, zinc-, magnesium-, potassium- and ammonium salts.
  • the ingredients of the final compound are mixed together, suitably at an elevated temperature that may range from 25 °C to 200 °C.
  • the mixing time does not exceed one hour and a time in the range from 2 to 30 minutes is usually adequate.
  • the mixing is suitably carried out in an internal mixer such as a Banbury mixer, or a Haake or Brabender miniature internal mixer.
  • a two roll mill mixer also provides a good dispersion of the additives within the elastomer.
  • inventive compounds are very well suited for the manufacture of shaped articles, especially shaped articles for high-purity applications such as fuel cell components (e.g. condenser caps), medical devices,
  • GPC samples were prepared by dissolution in THF. Polymer gel content was determined through conventional gravimetric analysis of the dry, hydrocarbon-insoluble fraction (insoluble in boiling cyclohexane, under agitation for a period of 60 minutes). ' Mixing was accomplished with the use of a miniature internal mixer (Brabender MIM) from C. W. Brabender, consisting of a drive unit (Plasticorder ® Type PL-V151) and a data interface module. Cure characteristics were determined with a Moving Die Rheometer (MDR) test carried out according to ASTM standard D-5289 on a Monsanto MDR 200 (E). The upper disc oscillated though a small arc of 1 degree.
  • MIM Moving Die Rheometer
  • Example 1 The following example illustrates our ability to produce, via a continuous process, a novel grade of IIR possessing an isoprene content of up to 5.0 mol %> and Mooney viscosity (ML 1+8 @ 125 °C) between 35 and 40 MU.
  • the monomer feed composition was comprised of 2.55 wt. % of isoprene (IP or IC5) and 27.5 wt. %> of isobutene (IP or IC4). This mixed feed was introduced into the continuous polymerization reactor at a rate of 5900 kg/hour. In addition, DVB was introduced into the reactor at a rate of 5.4 to 6 kg/hour.
  • Polymerization was initiated via the introduction of an AlCl 3 /MeCl solution (0.23 wt. % of A1C1 3 in MeCl) at a rate of 204 to 227 kg/hour.
  • the internal temperature of the continuous reaction was maintained between -95 and -100 °C through the use of an evaporative cooling process.
  • the newly formed polymer crumb was separated from the MeCl diluent with the use of an aqueous flash tank.
  • ca. 1 wt. %> of stearic acid was introduced into the polymer crumb.
  • Prior to drying 0.1 wt. % of Irganox® 1010 was added to the polymer. Drying of the resulting material was accomplished with the use of a conveyor oven. Table 1 details the characteristics of the final material.
  • Example 2 The following example illustrates our ability to produce, via a continuous process, a novel grade of IIR possessing an isoprene content of up to 8.0 mol %> and Mooney viscosity (ML 1+8 @ 125 °C) between 35 and 40 MU.
  • the monomer feed composition was comprised of 4.40 wt. % of isoprene (IP or IC5) and 25.7 wt. % of isobutene (IP or IC4). This mixed feed was introduced into the continuous polymerization reactor at a rate of 5900 kg/hour. In addition, DVB was introduced into the reactor at a rate of 5.4 to 6 kg/hour.
  • Polymerization was initiated via the introduction of an AlCl 3 /MeCl solution (0.23 wt. % of A1C1 3 in MeCl) at a rate of 204 to 227 kg/hour.
  • the internal temperature of the continuous reaction was maintained between -95 and -100 °C through the use of an evaporative cooling process.
  • the newly formed polymer crumb was separated from the MeCl diluent with the use of an aqueous flash tank. At this point, ca. 1 wt. % of stearic acid was introduced into the polymer crumb.
  • Prior to drying, 0.1 wt. % of Irganox® 1010 was added to the polymer.
  • Example 8 Invention This compound was based on the experimental high IP IIR described in
  • HVA-2 was added to the formulation. As can be seen from Figure 1 and Table 3, evidence of significant cure reactivity is observed for this system.
  • Example 9 Invention This compound was based on the experimental high IP IIR described in
  • HVA-2 was added to the formulation. As can be seen from Figure 1 and Table 3, evidence of significant cure reactivity is observed for this system.
  • the cure reactivity as detected for Examples 6 and 7 is significantly less than that observed for XL-10000 (Example 5).
  • the inclusion of 2.5 phr HNA-2 into formulations containing the high IP IIR samples (Example 8 and 9) resulted in a dramatic increase in cure reactivity.
  • the cure state achieved for Examples 8 and 9 is significantly higher than that observed for the XL- 10000 comparative formulation.
  • the stress-strain properties associated with the formulations described in Examples 8 and 9 are consistent with those observed for the standard XL- 10000 formulation.
  • the ultimate tensile strength measured for Examples 8 and 9 is superior to that determined for the XL- 10000 control.
  • Example 3 Example 4 Example 5 Example 6 Example 7 Example 8 Example 9 ⁇ Torque (dNm) 4.32 4.69 15.24 5.95 7.09 22.4 23.09 Tensile 300% (MPa) 2.11 2.09 N/A 3.28 4.47 N/A N/A Ultimate Tensile (MPa) 7.81 6.14 4.81 7.35 9.16 9.24 8.58 Ultimate Elongation (%) 788 742 129 493 476 139 126 Hardness, Shore A (Pts) 42 42 61 40 43 62 63

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne un composé de caoutchouc durcissable en peroxyde contenant des polymères présentant une viscosité de Mooney d'au moins 25 unités Mooney et une teneur en gel inférieure à 15 % en poids, comprenant des unités de répétition dérivées d'au moins un monomère isooléfine, plus de 4,1 % molaire d'unités de répétition dérivées d'au moins un monomère multi-oléofine, ainsi que, éventuellement, d'autres monomères copolymérisables, et des unités de répétition dérivées d'au moins un agent de réticulation multi-oléfine ne contenant pas de composés métalliques de transition ni de composés nitro-organique.
PCT/CA2005/000254 2004-02-23 2005-02-22 Compose de caoutchouc durcissable en peroxyde contenant du caoutchouc presentant une teneur elevee en isoprene butyle WO2005080452A1 (fr)

Applications Claiming Priority (2)

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CA2,458,741 2004-02-23
CA 2458741 CA2458741A1 (fr) 2004-02-23 2004-02-23 Formulations a base de butylcaoutchouc durcissable a l'aide de peroxydes, contenant du butylcaoutchouc a haute teneur en isoprene

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1814944A1 (fr) * 2004-11-18 2007-08-08 Lanxess Inc. Composition de caoutchouc comprenant une charge modifiée

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CA2489036C (fr) 2004-12-03 2013-02-12 Lanxess Inc. Compositions de butylcaoutchouc vulcanisables a l'aide de peroxydes et pouvant servir a fabriquer des articles en caoutchouc
JP2009506138A (ja) * 2005-08-26 2009-02-12 ランクセス・インコーポレーテッド 過酸化物硬化性ハイマルチオレフィンハロブチルアイオノマーの製造方法
EP1922363A1 (fr) * 2005-08-26 2008-05-21 Lanxess Inc. Compose de caoutchouc vulcanisable par un peroxyde a base d'ionomeres multiolefines d'halobutyle
KR20080039437A (ko) * 2005-08-26 2008-05-07 란세스 인크. 고 멀티올레핀 할로부틸 이오노머 함유 퍼옥시드 경화성고무 화합물
CA2578583C (fr) 2006-03-14 2014-06-03 Lanxess Inc. Ionomere butylique ayant une meilleure adhesion en surface
CA2598342C (fr) * 2006-09-08 2014-10-14 Lanxess Inc. Methode pour produire des composes elastomeres renforces de silice assurant une meilleure securite contre le grillage
CA2604409C (fr) 2006-12-22 2015-04-07 Lanxess Inc. Materiaux nanocomposites ionomeriques de butylcaoutchouc
CN102395631B (zh) 2009-02-13 2015-11-25 朗盛公司 用于减少有机体数目和/或防止有机体聚集的丁基离聚物以及由其制备的涂层
KR101832532B1 (ko) 2010-08-13 2018-02-26 아란세오 캐나다 인코퍼레이티드 부틸 이오노머 라텍스
TW201235359A (en) 2010-11-24 2012-09-01 Lanxess Inc Ionomers comprising pendant vinyl groups and processes for preparing same
EP2574635A1 (fr) 2011-09-28 2013-04-03 Lanxess Inc. Processus de production continue de compositions d'élastomère thermoplastique sans halogène
US9796794B2 (en) 2012-12-20 2017-10-24 LANXSS, Inc. Ionomer comprising pendant vinyl groups and processes for preparing same

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US3584080A (en) * 1968-03-07 1971-06-08 Polymer Corp Vulcanizable compositions comprising copolymers of an isoolefin and an aromatic divinyl compound
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US5994465A (en) * 1990-08-24 1999-11-30 Daikyo Gomu Seiko, Ltd. Rubber composition containing an organic compound having two maleimide groups and a rubber article for pharmaceuticals and medical treatment
CA2316741A1 (fr) * 2000-08-24 2002-02-24 Bayer Inc. Butylcaoutchouc a transformabilite amelioree et methode de production
CA2420244A1 (fr) * 2000-08-24 2002-02-28 Bayer Inc. Caoutchouc butyle a caracteristiques de traitement ameliorees et procede permettant de produire ce caoutchouc
CA2418884A1 (fr) * 2003-02-14 2004-08-14 Bayer Inc. Methode de production de caoutchouc butyle a haute teneur en isoprene

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US3511821A (en) * 1963-10-23 1970-05-12 Exxon Research Engineering Co Terpolymers of isobutylene-methylcyclopentadiene and a crosslinking agent
US3584080A (en) * 1968-03-07 1971-06-08 Polymer Corp Vulcanizable compositions comprising copolymers of an isoolefin and an aromatic divinyl compound
US5994465A (en) * 1990-08-24 1999-11-30 Daikyo Gomu Seiko, Ltd. Rubber composition containing an organic compound having two maleimide groups and a rubber article for pharmaceuticals and medical treatment
US5578682A (en) * 1995-05-25 1996-11-26 Exxon Chemical Patents Inc. Bimodalization of polymer molecular weight distribution
CA2316741A1 (fr) * 2000-08-24 2002-02-24 Bayer Inc. Butylcaoutchouc a transformabilite amelioree et methode de production
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CA2418884A1 (fr) * 2003-02-14 2004-08-14 Bayer Inc. Methode de production de caoutchouc butyle a haute teneur en isoprene

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Publication number Priority date Publication date Assignee Title
EP1814944A1 (fr) * 2004-11-18 2007-08-08 Lanxess Inc. Composition de caoutchouc comprenant une charge modifiée
JP2008520772A (ja) * 2004-11-18 2008-06-19 ランクセス・インク． 改質充填剤を含むゴム組成物
EP1814944A4 (fr) * 2004-11-18 2010-07-14 Lanxess Inc Composition de caoutchouc comprenant une charge modifiée

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