EP2181134A1 - Polymères modifiés à base de diènes conjugués ou de diènes conjugués et de composés vinylaromatiques, procédé pour leur production, et leur utilisation - Google Patents

Polymères modifiés à base de diènes conjugués ou de diènes conjugués et de composés vinylaromatiques, procédé pour leur production, et leur utilisation

Info

Publication number
EP2181134A1
EP2181134A1 EP08787042A EP08787042A EP2181134A1 EP 2181134 A1 EP2181134 A1 EP 2181134A1 EP 08787042 A EP08787042 A EP 08787042A EP 08787042 A EP08787042 A EP 08787042A EP 2181134 A1 EP2181134 A1 EP 2181134A1
Authority
EP
European Patent Office
Prior art keywords
compounds
modified polymers
conjugated dienes
polymers according
polyfunctional
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.)
Withdrawn
Application number
EP08787042A
Other languages
German (de)
English (en)
Inventor
Heike Kloppenburg
Thomas Gross
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.)
Lanxess Deutschland GmbH
Original Assignee
Lanxess Deutschland GmbH
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
Application filed by Lanxess Deutschland GmbH filed Critical Lanxess Deutschland GmbH
Publication of EP2181134A1 publication Critical patent/EP2181134A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/69—Polymers of conjugated dienes
    • C08G18/696—Polymers of conjugated dienes containing heteroatoms other than oxygen and other than the heteroatoms of copolymerised vinyl monomers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
    • C08C19/00—Chemical modification of rubber
    • C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
    • C08C19/42—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups
    • C08C19/44—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups of polymers containing metal atoms exclusively at one or both ends of the skeleton
    • 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
    • C08F257/00—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00
    • C08F257/02—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00 on to polymers of styrene or alkyl-substituted styrenes
    • 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
    • C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
    • C08F279/02—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00 on to polymers of conjugated dienes
    • 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
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/04—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to rubbers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L55/00—Compositions of homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C08L23/00 - C08L53/00
    • C08L55/02—ABS [Acrylonitrile-Butadiene-Styrene] polymers

Definitions

  • the present invention relates to coupled and heteroatoms containing modified
  • linking / coupling agent for the rubbers mentioned in the art in addition to the most diverse organic compounds with corresponding groups capable of linking with the living polymers, such as epoxy groups (DE-A 19 857 768), isocyanate groups,
  • DE-A 19 803 039 describes rubber compositions for high performance tire treads whose underlying rubbers have been partially coupled with tin, phosphorus, gallium or silicon compounds.
  • linking agents used hitherto are in some cases associated with still considerable disadvantages, e.g. that these by rare earths, especially by neodymium
  • the present invention therefore relates to modified polymers based on conjugated dienes or conjugated dienes and vinylaromatic compounds according to the following formula (I):
  • BR diene polymer, vinyl aromatic-diene copolymer
  • PUR polyurethane base body and n is greater than or equal to 2, preferably 2 to 10.
  • a product mixture of a polyfunctional isocyanate and / or thioisocyanate (component A) with a polyfunctional H-acidic compound (component B) is preferably used.
  • component A compounds of polyfunctional isocyanates and / or thioisocyanates can be used, which are described for example in Ullmann's Encyclopedia of the technical
  • ethylene diisocyanates such as 1,4-tetramethylene diisocyanate; 1,6-hexamethylene diisocyanate ("HDI"); 1,12-dodecane diisocyanate; cyclobutane 1,3-diisocyanate; cyclohexane-1,3- and 1,4-diisocyanate; 1-isocyanato-3,3,5-trimethyl- 5-isocyanatomethylcyclohexane; 2,4- and 2,6-hexahydrotoluenediisocyanate; dicyclohexylmethane
  • HDI 1,6-hexamethylene diisocyanate
  • 1,12-dodecane diisocyanate 1,12-dodecane diisocyanate
  • cyclobutane 1,3-diisocyanate cyclohexane-1,3- and 1,4-diisocyanate
  • reaction products of polyfunctional isocyanates and / or thioisocyanates component A
  • polyfunctional H-acid compounds component B
  • polyfunctional H-acidic compounds can be used, which include, inter alia, thiols, alcohols and / or amines, as they are e.g. in Ullmann's Encyklopadie der ischen Chemie, 4th Edition, Weinheim: Verlag Chemie, Volume 19,
  • Component B contains at least one compound of structure B. - -
  • Y O, S or NR, where R is hydrogen, an aliphatic hydrocarbon radical having 2 to 200, preferably 3 to 10 C-atoms, a cycloaliphatic hydrocarbon radical having 4 to 200, preferably 5 to 10 C atoms, an aromatic hydrocarbon radical 6 to 200, preferably 6 to 13 C atoms or an arylaliphatic hydrocarbon radical having 8 to 200, preferably 8 to 12 C atoms, said aliphatic, cycloaliphatic, aromatic and arylaliphatic hydrocarbon radicals each optionally one or more heteroatoms from the series O , N, S may contain
  • T is an oligomeric structure having 2 to 1000 carbon atoms, preferably 2 to 100 carbon atoms, which may contain double bonds and, for example, by polymerization of dienes with OH-containing comonomers, by polymerization of dienes with comonomers containing epoxide groups and subsequent hydrolysis or subsequent Substitution of an oligomer having OH-containing groups was formed, an aliphatic hydrocarbon radical having 2 to 200, preferably 2 to 10 carbon atoms, a cycloaliphatic hydrocarbon radical having 4 to 200, preferably 5 to 10 carbon atoms, an aromatic hydrocarbon radical having 6 to 200 , preferably 6 to 13 C atoms or an arylaliphatic hydrocarbon radical having 8 to 200, preferably 8 to 12, C atoms, where the said oligomeric, aliphatic, cycloaliphatic, aromatic and arylaliphatic hydrocarbon radicals in each case optionally contain one or more heteroatoms from the series O, N, S included, stands.
  • reaction products of polyfunctional H-acidic compounds with the above-described polyfunctional isocyanates and thioisocyanates containing free H-acidic groups.
  • a PUR catalyst may be present in the reaction with the polyfunctional H-acidic compounds. PUR catalyst addition can be done at any time. - -
  • Amines such as dibutyltin dilaurate, stannous octoate or 1,4-diazabicyclo [2.2.2] octane.
  • BR within the meaning of the invention include diene polymers and vinyl aromatic-diene copolymers prepared from conjugated dienes, such as e.g. 1,3-butadiene, 2,3-dimethyl-1,3-butadiene, 3-butyl-1,3-octadiene, isoprene, piperylene, 1,3-hexadiene, 1,3-octadiene, 2-phenyl-1, 3-butadiene, preferably 1,3-butadiene and isoprene or from the above-described conjugated dienes with vinyl aromatics, such as Styrene and divinylbenzene, preferably 1,3-butadiene, isoprene and styrene.
  • conjugated dienes such as e.g. 1,3-butadiene, 2,3-dimethyl-1,3-butadiene, 3-butyl-1,3-octadiene, isoprene, piperylene, 1,3-hexadiene
  • the quantitative ratio of BR: PUR is 100: 0.01 to 30, preferably 100: 0.02 to 10 and particularly preferably 100: 0.05 to 5.
  • the invention also relates to a process for the preparation of the polymers according to the invention, according to which first the compounds containing conjugated dienes are polymerized alone or together with vinyl aromatic compounds, then these polymers are reacted with compounds of polyfunctional isocyanates and / or thioisocyanates and then containing this polymer solution polyfunctional, H-acidic compounds, preferably thiols, alcohol and / or amines, are reacted.
  • the preparation of the coupled and modified polymers according to the invention is preferably carried out in three steps.
  • a diene polymer and / or vinyl aromatic-diene copolymer is prepared.
  • the first step of preparing the polymers of this invention is generally carried out by reacting a catalyst system with the particular monomer or monomers to form the polymers. - -
  • the preparation of the BR component is carried out according to the methods known in the prior art.
  • the catalysts used are preferably compounds of the rare earth metals, as described in more detail in EP-A 011184 or EP-A 1245600. Also possible are all known for the polymerization Ziegler-Natta catalysts, such as those based on titanium, cobalt -, vanadium or nickel compounds and based on
  • the said Ziegler-Natta catalysts can be used both individually and in admixture with each other. Also possible is the use of anionic catalysts, e.g. Systems based on butyllithium.
  • Ziegler-Natta catalysts based on rare earth metal compounds, such as cerium, lanthanum, praseodymium, gadolinium or neodymium compounds, which are soluble in hydrocarbons, are preferably used.
  • the corresponding salts of rare earth metals are particularly preferably used as Ziegler-Natta catalysts, such as neodymium carboxylates, in particular neodymium neodecanoate, neodymium octanoate, neodymium naphthenate, neodymium-2,2-diethylhexanoate or neodymium-2,2-diethylheptanoate, and the corresponding salts of lanthanum or praseodymium.
  • the usable Ziegler-Natta catalysts also comprise catalyst systems
  • the polymerization can be carried out in one or more stages by conventional methods or in batchwise or continuous mode. Preference is given to continuous operation in a reactor cascade consisting of several, preferably at least 2, in particular 2 to 5, series-connected reactors.
  • This polymerization can be carried out in a solvent and / or solvent mixture.
  • inert aprotic solvents e.g. paraffinic hydrocarbons, such as isomeric pentanes, hexanes, heptanes, octanes, decanes, 2,4-trimethylpentane, cyclopentane, cyclohexane, methylcyclohexane, ethylcyclohexane or 1,4-dimethylcyclohexane, or aromatic
  • Hydrocarbons such as benzene, toluene, ethylbenzene, xylene, diethylbenzene or propylbenzene. These solvents may be used singly or in combination. Preferred are cyclohexane and n-hexane. Also possible is the mixture with polar solvents.
  • the amount of solvent in the process according to the invention is usually 1000 to 100 g, preferably 500 to 150 g, based on 100 g of the total amount of monomer used.
  • the polymerization reaction is preferably carried out in the presence of the aforementioned inert aprotic solvents.
  • the polymerization temperature can vary within wide limits and is generally in the range from 0 ° C. to 200 ° C., preferably from 40 ° C. to 130 ° C.
  • the reaction time likewise varies in wide ranges from a few minutes to a few hours. Usually, the
  • the polymerization according to the invention of the unsaturated monomers in the presence of said Ziegler-Natta catalysts may preferably be carried out until complete conversion of the employed
  • Monomers are performed. Of course, it is also possible to prematurely interrupt the polymerization, depending on the desired polymer properties, for example, in the conversion of about 80% of the monomers.
  • the unreacted diene can be separated by, for example, a flash stage.
  • Suitable aprotic organic solvents are, for example: pentanes, hexanes, heptanes, cyclohexane, methylcyclopentane, benzene, toluene, ethylbenzene, preferably hexanes, cyclohexane, toluene, very particularly preferably hexane.
  • the reaction of the diene polymers or vinylaromatic-diene copolymers with the compounds is preferably carried out in situ without intermediate isolation of the polymers, the diene polymers or vinylaromatic-diene copolymers after polymerization first being reacted with compounds of the polyfunctional isocyanates and / or thioisocyanates (component A) become.
  • interfering compounds which could impair the reaction should preferably not be present.
  • interfering compounds are e.g. Carbon dioxide, oxygen,
  • the amount of organic solvents can be easily determined by appropriate preliminary tests and is usually 100 to 1000 g, preferably 150 to 500 g, based on a 100 g of the total amount of monomer used.
  • the erfmdungswashe process is usually carried out at temperatures from 0 0 C to 200 0 C, preferably 30 0 C to 130 0 C.
  • the reaction can also be carried out at atmospheric pressure and at elevated pressure (1 to 10 bar).
  • the reaction time is preferably relatively short. It is in the range of about 1 minute to about 1 hour.
  • This polymer solution then obtained is then preferably in a third step without intermediate isolation of the polymers in situ with polyfunctional, H-acidic compounds, preferred
  • a PUR catalyst for the reaction of the polymer solution thus obtained with the component B, a PUR catalyst can also be used. This may be the PUR catalysts already mentioned above.
  • the reaction can be accelerated.
  • the reaction is carried out at temperatures of 0 0 C to 150 0 C, preferably at 30 0 C to 130 0 C.
  • the reaction can be followed by titration of the NCO content or by evaluation of the NCO band of the IR spectrum at 2260 to 2275cm '1. As a rule, response times are sufficiently less than 24 hours.
  • the molecular weight of the coupled and modified polymers of the invention can vary widely.
  • the number average molecular weight ranges from about 100,000 to about 2,000,000.
  • reaction mixture it is possible to treat the reaction mixture with termination reagents, as mentioned above, which contain active hydrogens, such as alcohols or water, or mixtures thereof.
  • active hydrogens such as alcohols or water, or mixtures thereof.
  • Antioxidants are added before the modified polymer is isolated.
  • the separation of the polymer according to the invention is carried out in the usual manner, for example by
  • the flocculated polymer is then removed from the resulting medium by, for example, centrifuging or extruding. Residual solvent and other volatile Components can be removed from the isolated polymer by heating, optionally under reduced pressure or in a forced air stream.
  • the customary compounding components such as fillers, dye, pigments, emollients and reinforcing agents.
  • the known rubber auxiliaries and crosslinking agents can be added.
  • the modified polymers of the invention can be used in a known manner for the preparation of vulcanizates or rubber moldings of all kinds.
  • the invention also relates to the use of the modified polymers according to the invention, for the production of tires and tire components, golf balls and technical rubber articles and rubber-reinforced plastics, such as. ABS and HIPS plastics.
  • the polymerizations were carried out under exclusion of air and moisture under nitrogen.
  • the solvent used was dry and oxygen-free technical hexane.
  • the polymerization was carried out according to the batch size in an autoclave with 2L to 20L volume.
  • the sales determinations were made gravimetrically; In this case, the polymer solutions after sampling (still with solvent and monomer) and after drying (at 65 0 C in a vacuum oven) were weighed.
  • the Mooney measurement ML 1 + 4 (100) was preheated at an instrument from Alpha with the large rotor after one minute for 4 minutes as measured at 100 0 C.
  • a solution of diisobutylaluminum hydride in hexane (DIBAH; Al (C 4 H 9 ) 2 H) is added to a solution of 13% by weight of 1,3-butadiene in technical hexane with stirring in a dried nitrogen-overlaid 20 l steel reactor ), a solution of ethylaluminum sequichloride in hexane (EASC, Al 2 (C 2 Hs) 3 CIs) in equimolar amount to Neodymversatat and a
  • the polymer solution is stabilized with the stabilizer 2.6 g Irganox 1520 dissolved in 100 ml of hexane and the polymer is then precipitated with about 10 1 of ethanol and dried at 60 0 C in a vacuum oven.

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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)
  • General Chemical & Material Sciences (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention concerne des polymères à base de diènes conjugués ou de diènes conjugués et de composés vinylaromatiques, un procédé pour leur production, et leur utilisation.
EP08787042A 2007-08-16 2008-08-08 Polymères modifiés à base de diènes conjugués ou de diènes conjugués et de composés vinylaromatiques, procédé pour leur production, et leur utilisation Withdrawn EP2181134A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102007038442A DE102007038442A1 (de) 2007-08-16 2007-08-16 Modifizierte Polymere auf Basis von konjugierten Dienen oder von konjugierten Dienen und vinylaromatischen Verbindungen, ein Verfahren zu deren Herstellung sowie deren Verwendung
PCT/EP2008/060447 WO2009021917A1 (fr) 2007-08-16 2008-08-08 Polymères modifiés à base de diènes conjugués ou de diènes conjugués et de composés vinylaromatiques, procédé pour leur production, et leur utilisation

Publications (1)

Publication Number Publication Date
EP2181134A1 true EP2181134A1 (fr) 2010-05-05

Family

ID=40010772

Family Applications (1)

Application Number Title Priority Date Filing Date
EP08787042A Withdrawn EP2181134A1 (fr) 2007-08-16 2008-08-08 Polymères modifiés à base de diènes conjugués ou de diènes conjugués et de composés vinylaromatiques, procédé pour leur production, et leur utilisation

Country Status (12)

Country Link
US (1) US20110251348A1 (fr)
EP (1) EP2181134A1 (fr)
JP (2) JP2010536946A (fr)
KR (1) KR101259231B1 (fr)
CN (1) CN101802041B (fr)
BR (1) BRPI0815390A2 (fr)
DE (1) DE102007038442A1 (fr)
RU (1) RU2446182C2 (fr)
SA (1) SA08290507B1 (fr)
TW (1) TWI422606B (fr)
WO (1) WO2009021917A1 (fr)
ZA (1) ZA201001080B (fr)

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JP6480174B2 (ja) * 2014-12-17 2019-03-06 ヘンケルジャパン株式会社 積層シート用接着剤
CN107417879B (zh) * 2016-05-24 2020-06-09 北京化工大学 一种高性能轮胎用溶聚丁苯橡胶-聚氨酯弹性体材料及制备方法
MX2020001733A (es) 2017-08-18 2020-03-20 Fina Technology Polifarnesenos epoxidizados y metodos para producirlos.
CN107540812B (zh) * 2017-09-08 2020-10-27 北京化工大学 一种热塑性溶聚丁苯橡胶-聚氨酯弹性体材料及制备方法
CN114423814A (zh) * 2019-09-20 2022-04-29 株式会社普利司通 橡胶组合物及使用其获得的轮胎
DE102020118314A1 (de) 2020-07-10 2022-01-13 Ask Chemicals Gmbh Mittel zur Reduzierung von Sandanhaftungen

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RU2446182C2 (ru) 2012-03-27
TW200920757A (en) 2009-05-16
JP2014198855A (ja) 2014-10-23
JP2010536946A (ja) 2010-12-02
CN101802041B (zh) 2013-11-06
BRPI0815390A2 (pt) 2015-02-10
US20110251348A1 (en) 2011-10-13
TWI422606B (zh) 2014-01-11
RU2010109440A (ru) 2011-09-27
SA08290507B1 (ar) 2012-06-23
WO2009021917A1 (fr) 2009-02-19
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