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WO2009138349A1 - Caoutchoucs diéniques fonctionnalisés à forte teneur en composés vinylaromatiques - Google Patents

Caoutchoucs diéniques fonctionnalisés à forte teneur en composés vinylaromatiques Download PDF

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Publication number
WO2009138349A1
WO2009138349A1 PCT/EP2009/055495 EP2009055495W WO2009138349A1 WO 2009138349 A1 WO2009138349 A1 WO 2009138349A1 EP 2009055495 W EP2009055495 W EP 2009055495W WO 2009138349 A1 WO2009138349 A1 WO 2009138349A1
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Prior art keywords
rubber
weight
vinyl aromatic
content
rubbers
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.)
Ceased
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PCT/EP2009/055495
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German (de)
English (en)
Inventor
Norbert Steinhauser
Thomas Gross
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Lanxess Deutschland GmbH
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Lanxess Deutschland GmbH
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Filing date
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Publication of WO2009138349A1 publication Critical patent/WO2009138349A1/fr
Anticipated expiration legal-status Critical
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L19/00—Compositions of rubbers not provided for in groups C08L7/00 - C08L17/00
    • C08L19/006—Rubber characterised by functional groups, e.g. telechelic diene polymers
    • 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
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L13/00—Compositions of rubbers containing carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L15/00—Compositions of rubber derivatives
    • 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
    • C08K3/02—Elements
    • C08K3/04—Carbon
    • 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
    • C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons

Definitions

  • the present invention relates to functionalized high vinyl aromatic-containing diene rubbers and their preparation, rubber mixtures containing these functionalized high vinyl aromatic-containing diene rubbers and their use for the production of rubber vulcanizates, which are used in particular for the production of highly reinforced rubber moldings.
  • Particularly preferred is the use in the production of tires which have a particularly low rolling resistance, a particularly high wet skid resistance and abrasion resistance.
  • wet skid resistance, rolling resistance and abrasion resistance of a tire depend in large part on the dynamic mechanical properties of the rubbers used to build the tire.
  • rubbers are used for the tire tread with a high resiliency at higher temperatures.
  • rubbers having a high damping factor at low temperatures are advantageous for improving wet skid resistance.
  • mixtures of different rubbers are used in the tread. Usually become
  • Double bond-containing anionically polymerized solution rubbers such as solution polybutadiene and solution styrene-butadiene rubbers, have advantages over corresponding emulsion rubbers in the production of rolling resistance-poor tire treads.
  • the advantages are u.a. in the controllability of the vinyl content and the associated glass transition temperature and molecular branching. This results in practical advantages in the relation of wet skid resistance and rolling resistance of the
  • EP-A 1 000 971 discloses higher-functionalized, carboxyl-containing copolymers of vinylaromatics and dienes having a content of 1,2-linked diene (vinyl content) of up to 60% and a content of bonded vinylaromatics of up to 40%.
  • the introduction of the functional groups takes place after completion of the anionic polymerization by addition of appropriate reagents to the rubber double bonds along the polymer chain. In this way, it is possible to achieve a higher degree of functionalization than with end-group modification, and functional groups capable of forming hydrogen bonds can be introduced.
  • Such functional groups form particularly advantageous interactions with the polar groups on the surface of the added filler.
  • skid resistance of tires can be improved by the use of high styrene styrene-butadiene copolymers in the tire tread, e.g. in US-A 5082901 and US-A 7193004.
  • the improvement in skid resistance is usually accompanied by an increase in rolling resistance.
  • Such styrene-butadiene copolymers with high styrene content are therefore preferred for racing tires and
  • the functionalized high vinylaromatic diene rubbers of the invention incorporated in tires, have these properties and show an improvement in wet skid resistance as well as in rolling resistance and abrasion in comparison with functionalized diene rubbers having a lower vinyl aromatic content.
  • the rubbers of the invention also show superior
  • the present invention therefore relates to novel functionalized vinylidene rubbers containing high vinyl aromatics, characterized in that it contains from 30 to 60% by weight, preferably from 30 to 45% by weight, of copolymerized vinylaromatic monomers and a content of dienes of from 40 to 70% by weight.
  • Vinylaromatic monomers that can be used for the polymerization include, for example, styrene, o-, m- and / or p-methylstyrene, p-tert-butylstyrene, ⁇ -methylstyrene, vinylnaphthalene, divinylbenzene, trivinylbenzene and / or divinylnaphthalene. Styrene is particularly preferably used.
  • 1,3-butadiene, isoprene, 1,3-pentadiene, 2,3-dimethylbutadiene, 1-phenyl 1-1, 3-butadiene and / or 1,3-hexadiene are preferred. Particular preference is given to using 1,3-butadiene and / or isoprene.
  • the rubbers based on dienes and vinylaromatic monomers according to the invention which have a content of 0.02 to 3% by weight of bonded functional groups, preferably have number average molecular weights of 50,000 to 2,000,000 g / mol
  • the rubbers according to the invention may be groups such as carboxyl, hydroxyl, amine, carboxylic ester, carboxylic acid amide or
  • Wear sulfonic acid groups Preferred are carboxyl or hydroxyl groups.
  • the vinyl aromatic monomer is styrene
  • the diene is 1,3-butadiene
  • the functional group is carboxyl or hydroxyl
  • the rubbers according to the invention are preferably prepared by copolymerization of dienes and vinylaromatic monomers in solution and subsequent introduction of functional groups. - A -
  • the invention also relates to a process for the preparation of the rubbers of the invention, according to which the dienes and vinyl aromatic monomers are copolymerized in solution to rubber, then the functional groups or their salts are introduced into the diene rubber and then the solvent with hot water and / or water vapor at temperatures of 50 to 200 0 C, optionally under vacuum, is removed.
  • the rubbers of the invention for the rubber mixtures of the invention are preferably prepared by anionic solution polymerization or by polymerization by means of coordination catalysts.
  • Coordination catalysts are to be understood as meaning Ziegler-Natta catalysts or monometallic catalyst systems.
  • Preferred coordination catalysts are those based on Ni, Co, Ti, Nd, V, Cr or
  • Initiators for anionic solution polymerization are those based on alkali or alkaline earth metals, e.g. n-butyl lithium.
  • the known randomizers and control agents can be used for the microstructure of the polymer, e.g. Potassium tert-amylate and tert-butoxyethoxyethane.
  • Such solution polymerizations are known and e.g. in I. Franta
  • the solvents used are preferably inert aprotic solvents, e.g. paraffinic hydrocarbons, such as isomeric pentanes, hexanes, heptanes, octanes, decanes, cyclopentane, cyclohexane, methylcyclohexane, ethylcyclohexane or 1, 4-dimethylcyclohexane or aromatic hydrocarbons, such as benzene, toluene, ethylbenzene, xylene, diethylbenzene or propylbenzene used. These solvents may be used singly or in combination. Preferred are cyclohexane and n-hexane. Also possible is the mixture with polar solvents.
  • paraffinic hydrocarbons such as isomeric pentanes, hexanes, heptanes, octanes, decanes, cyclopentane, cyclohe
  • the amount of solvent in the process according to the invention is usually 1000 to 100 g, preferably 700 to 200 g, based on 100 g of the total amount of monomer used. But it is also possible to polymerize the monomers used in the absence of solvents.
  • the polymerization temperature can vary widely and is generally in the range from 0 ° C. to 200 ° C., preferably from 40 ° C. to 130 ° C.
  • the reaction time also varies in wide ranges from a few minutes to a few hours.
  • the polymerization within a period of about 30 minutes to 8 hours, preferably 1 to 4 hours, performed. It can be carried out both at atmospheric pressure and at elevated pressure (1 to 10 bar).
  • the functional groups are introduced according to the prior art in single- or multistage reactions by addition of appropriate functionalizing reagents to the double bonds of the rubber or by abstraction of allylic hydrogen atoms and subsequent reaction with functionalizing reagents.
  • the carboxyl groups can be introduced into the rubber in various ways.
  • Carboxyl-supplying compounds such as CO2 are added to metallated rubbers, or by the transition metal-catalyzed hydrocarboxylation known in the art, or by treating the rubber with carboxyl-containing compounds, for example carboxyl-containing mercaptans.
  • the determination of the carboxyl group content can be carried out by known methods, e.g. Titration of the free acid, spectroscopy or elemental analysis.
  • the introduction of the carboxyl groups into the rubber takes place after the polymerization of the monomers used in solution by reaction of the resulting
  • R 1 is a linear, branched or cyclic C 1 -C 35 alkylene or alkenylene group which may optionally be substituted by up to 3 further carboxyl groups, or may be interrupted by nitrogen, oxygen or sulfur atoms, or an aryl group stands, and
  • X is hydrogen or a metal ion, e.g. Li, Na, K, Mg, Zn, Ca or a, optionally with Ci-C35-alkyl, alkenyl, cycloalkyl or aryl groups substituted ammonium ion.
  • a metal ion e.g. Li, Na, K, Mg, Zn, Ca or a, optionally with Ci-C35-alkyl, alkenyl, cycloalkyl or aryl groups substituted ammonium ion.
  • Preferred carboxymercaptans are thioglycolic acid, 2-mercaptopropionic acid (thiolactic acid), 3-mercaptopropionic acid, 4-mercaptobutyric acid, mercaptohexanoic acid, mercaptooctanoic acid, mercaptodecanoic acid, mercaptoundecanoic acid, mercaptododecanoic acid, mercaptooctadecanoic acid, 2-mercaptosuccinic acid and their alkali, alkaline earth, zinc or ammonium salts.
  • 3-mercaptopropionic acid and its lithium, sodium, potassium, magnesium, calcium, zinc or ammonium, ethylammonium, diethylammonium, triethylammonium, stearylammonium and cyclohexylammonium salts is particularly preference is given to 2- and 3-mercaptopropionic acid, mercaptobutyric acid and 2- Mercaptosuccinic acid and their lithium, sodium, potassium, magnesium, calcium, zinc or ammonium salts used.
  • the reaction of the Carboxylmercaptane is introduced with the rubber in a solvent for example hydrocarbons such as pentane, hexane, cyclohexane, benzene and / or toluene at temperatures from 40 to 150 0 C, in the presence of radical initiators, such as peroxides, especially acyl peroxides, such as dilauroyl peroxide and dibenzoyl peroxide, and ketal peroxides, such as l, l-di (tert-butylperoxy) -3,3,5-trimethylcyclohexane, further azo initiators, such as azobisisobutyronitrile, Benzpinakolsilylethern or in the presence of photoinitiators and visible or UV light.
  • radical initiators such as peroxides, especially acyl peroxides, such as dilauroyl peroxide and dibenzoyl peroxide, and ketal peroxide
  • the amount of Carboxylmercaptanen to be used depends on the desired content of bound carboxyl groups or their salts in the diene rubber of the invention.
  • the carboxylic acid salts can also be prepared after the introduction of the carboxylic acid groups into the rubber by neutralizing them.
  • the hydroxyl groups may e.g. are introduced into the rubber by epoxidizing the rubber and then ringöffhet the epoxy groups, the rubber hydroborated and then treated with alkaline hydrogen peroxide solution or by passing the rubber with hydroxyl-containing compounds, such as hydroxyl-containing
  • the introduction of the hydroxyl groups into the rubber preferably takes place after polymerization of the monomers used in solution by reaction of the resulting polymers, if appropriate in the presence of radical initiators, with hydroxylmercaptans of the formula
  • R 2 is a linear, branched or cyclic Cj ⁇ ß.Alkylen- or alkenylene group, which may optionally be substituted with up to 3 further hydroxyl groups, or may be interrupted by nitrogen, oxygen or sulfur atoms, or
  • Arylsubstituenten may have, or is an aryl group.
  • Preferred hydroxyl mercaptans are thioethanol, 2-mercaptopropanol, 3-mercaptopropanol, 4-mercaptobutanol, 6-mercaptohexanol, mercaptooctanol, mercaptodecanol, mercaptododecanol, mercaptohexadecanol, mercaptooctadecanol.
  • Particularly preferred are mercaptoethanol, 2- and 3-mercaptopropanol and mercaptobutanol.
  • reaction of the hydroxyl mercaptans with the rubber is carried out in one
  • Carboxylic acid ester and amino groups can be prepared in a corresponding manner from mercaptocarboxylic acid esters and mercaptoamines of the general formula
  • R 3 is a linear, branched or cyclic C 1 -C 36 -alkylene or -alkylene group which may optionally be substituted by up to 3 further carboxylic acid esters or amino groups, or may be interrupted by nitrogen, oxygen or sulfur atoms, or for an aryl group stands, and
  • R 4 is a linear, branched or cyclic C 1 -C 36 -alkyl or alkenyl group which may optionally be interrupted by nitrogen, oxygen or sulfur atoms, or represents a phenyl group which may have up to 5 alkyl substituents or aromatic substituents,
  • R 5 , R 6 is hydrogen or a linear, branched or cyclic Ci-C 36 -AlkVl- or alkenyl group, optionally substituted by nitrogen, oxygen or
  • Sulfur atom may be interrupted, or represents a phenyl group which may have up to 5 alkyl substituents or aromatic substituents.
  • the present invention furthermore relates to rubber mixtures comprising the diene rubbers according to the invention and additionally from 10 to 500 parts by weight of filler, based on
  • Suitable fillers for the rubber mixtures according to the invention are all known fillers used in the rubber industry. These include both active and inactive fillers. To mention by way of example are:
  • silicic acids prepared for example by precipitation of solutions of silicates or flame hydrolysis of silicon halides with specific surface areas of 5-1000, preferably 20-400 m 2 / g (BET surface area) and with primary particle sizes of 10-400 nm.
  • the silicic acids may optionally also as mixed oxides with other metal oxides, such as
  • synthetic silicates such as aluminum silicate, alkaline earth silicate such as magnesium silicate or calcium silicate, with BET surface areas of 20-400 m 2 / g and primary particle diameters of 10-400 nm;
  • Glass fibers and glass fiber products (mats, strands) or glass microspheres;
  • Metal oxides such as zinc oxide, calcium oxide, magnesium oxide, aluminum oxide;
  • Metal carbonates such as magnesium carbonate, calcium carbonate, zinc carbonate;
  • Metal hydroxides e.g. Aluminum hydroxide, magnesium hydroxide;
  • Arc processes were prepared and have BET surface areas of 9-200 m 2 / g, eg Super Abrasion Furnace (SAF), Intermediate SAF, Intermediate SAF Low Structure (ISAF-LS), Intermediate SAF High Modulus (ISAF-HM) -, Intermediate SAF Low Modulus (ISAF-LM), Intermediate SAF High Structure (ISAF-HS), Conductive Furnace (CF), Super Conductive Furnace (SCF), High Abrasion Furnace (HAF), High abrasion
  • HAF-LS Furnace Low Structure
  • FF-HS Fine Furnace High Structure
  • SRF Semi Reinforcing Furnace
  • XCF Extra Conductive Furnace
  • FEF Fast Extruding Furnace
  • F-LS Fast Extruding Furnace Low Structure
  • F-HS Fast Extruding Furnace High Structure
  • GPF-HS General Purpose Furnace
  • APIF All Purpose Furnace
  • SRF-LS, SRF-LM, SRF-HS, SRF-HM and Medium Thermal (MT) carbon black or, according to the ASTM classification, the types N 110, N 219, N220, N231, N234, N242 , N294, N326, N327, N330, N332, N339, N347, N351, N356, N358, N375, N472, N539, N550, N568, N650, N660 N754, N762, N765, N774, N787 and N990 carbon blacks
  • Rubber gels in particular those based on polybutadiene, butadiene-styrene copolymers,
  • Butadiene-acrylonitrile copolymers and polychloroprene Preference is given to using finely divided silicas and / or carbon blacks as fillers.
  • the fillers mentioned can be used alone or in a mixture.
  • the rubbers contain as further constituents as fillers a mixture of light fillers, such as highly disperse silicic acids, and carbon blacks, wherein the mixing ratio of light fillers to carbon blacks at 0.0: 1 to 50: 1 is preferably 0.05: 1 up to 20: 1. This preferably also means 0.05: 1 to 20, preferably 0.1 to 15.
  • the fillers are in this case used in amounts ranging from 10 to 500 parts by weight based on 100 parts by weight of rubber. Preferably, 20 to 200 parts by weight are used.
  • the rubber mixtures according to the invention may contain, in addition to the above-mentioned functionalized diene rubber, other rubbers, such as natural rubber or else others
  • Synthetic rubbers Their amount is usually in the range of 0.5 to 85, preferably 10 to 70 wt .-%, based on the total amount of rubber in the rubber mixture. The amount of additionally added rubbers depends again on the particular intended use of the rubber mixtures according to the invention.
  • Additional rubbers are, for example, natural rubber and synthetic rubber.
  • NBR-butadiene-acrylonitrile copolymers having acrylonitrile contents of 5-60
  • EPDM - ethylene-propylene-diene terpolymers and mixtures of these rubbers.
  • natural rubber emulsion SBR and solution SBR with a glass transition temperature above -50 0 C, polybutadiene rubber with high cis content (> 90%), with catalysts based on Ni, Co, Ti or Nd, as well as polybutadiene rubber with a vinyl content of up to 80% and their mixtures of interest.
  • the rubber mixtures of the invention may contain other rubber auxiliaries, for example, improve the processing properties of the rubber mixtures, the crosslinking of the rubber mixtures serve (crosslinking agents), improve the chemical and / or physical properties of the vulcanizates prepared from the inventive rubber mixtures for their specific application, the Improve interaction between rubber and filler or serve to attach the rubber to the filler.
  • the crosslinking of the rubber mixtures serve (crosslinking agents)
  • improve the chemical and / or physical properties of the vulcanizates prepared from the inventive rubber mixtures for their specific application the Improve interaction between rubber and filler or serve to attach the rubber to the filler.
  • Rubber auxiliaries are e.g. Crosslinking agents, such as e.g. Sulfur or sulfur donating compounds, reaction accelerators, anti-aging agents, heat stabilizers, light stabilizers, antiozonants, processing aids, plasticizers, tackifiers, blowing agents,
  • Crosslinking agents such as e.g. Sulfur or sulfur donating compounds, reaction accelerators, anti-aging agents, heat stabilizers, light stabilizers, antiozonants, processing aids, plasticizers, tackifiers, blowing agents,
  • Dyes pigments, waxes, extenders, organic acids, silanes, retarders, metal oxides and activators.
  • the rubber mixtures according to the invention also contain fillers, oils and / or further auxiliaries, these may be e.g. be prepared by mixing in suitable mixing equipment, such as kneaders, rollers or extruders.
  • the rubber mixtures according to the invention are preferably prepared by first carrying out the polymerization of said monomers in solution which introduces functional groups into the vinylvinyl containing high vinyl aromatic compound and, after completion of the polymerization and introduction of the functional groups, the diene rubber according to the invention with anti-aging agents and optionally
  • the preferred process oils are DAE (Distillate Aromatic Extract), TDAE (Treated Distillate Aromatic Extract), MES (Mild Extraction Solvates), RAE (Residual Aromatic Extract), TRAE (Treated Residual Aromatic Extract), naphthenic and heavy naphthenic oils.
  • the dienes and vinyl aromatic monomers are copolymerized in solution to rubber, then introduced the functional groups or their salts in the diene rubber and then the solvent-containing rubber mixed with process oil, wherein during or after the
  • Invention is added after the functionalization filler and / or process oil and optionally further rubbers and rubber auxiliaries.
  • the filler is added to the process oil after introduction of the functional groups.
  • Another object of the present invention is the use of the rubber mixtures according to the invention for the production of vulcanizates, which in turn serve for the production of highly reinforced rubber moldings, in particular for the production of tires.
  • Example 1 Synthesis of styrene-butadiene rubber containing high styrene (Comparative Example) An inerted 20 L reactor was charged with 8.5 kg of hexane, 930 g of 1,3-butadiene, 570 g of styrene, 10.3 mmol of tert-butoxyethoxyethane, 1, 1 mmol of potassium tert-amylate and 14 mmol of butyllithium filled and the
  • Vinyl content (IR spectroscopy): 38% by weight; Styrene content (IR spectroscopy): 24% by weight, glass transition temperature (DSC): -37 ° C .; number average molecular weight M n (GPC, PS standard): 239000 g / mol; MJM n: 1.62; COOH functionalization degree (titration with methanolic KOH solution): 55 meq./kg
  • Example 4 a-c Rubber mixtures
  • Styrene-butadiene rubber with lower styrene content from Example 3 (rubber mixture 4c) included.
  • the mixture components are listed in Table 1.
  • the mixtures (without sulfur and accelerator) were prepared in a 1.5 L kneader.
  • the mixture components sulfur and accelerator were then admixed on a roll at 40 0 C.
  • Example 5 a-c Vulcanizate Properties
  • Examples 4a-c The mixtures of Examples 4a-c according to Table 1 were vulcanized at 160 ° C. for 20 minutes. The properties of the corresponding vulcanizates are listed in Table 2 as Examples 5a-c.
  • the vulcanizate of Example 5b according to the invention is characterized by a high impact resilience at 60 0 C, a low tan ⁇ -
  • Example 5b by a high tan ⁇ value in the dynamic damping at 0 0 C from.
  • Example 5b the vulcanizate of Example 5b according to the invention is characterized by a low degree of DIN abrasion.

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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)

Abstract

L'invention concerne des caoutchoucs diéniques fonctionnalisés à forte teneur en composés vinylaromatiques, leur fabrication, des mélanges de caoutchoucs renfermant ces caoutchoucs diéniques fonctionnalisés à forte teneur en composés vinylaromatiques, et leur utilisation pour la fabrication de vulcanisats de caoutchoucs.
PCT/EP2009/055495 2008-05-16 2009-05-06 Caoutchoucs diéniques fonctionnalisés à forte teneur en composés vinylaromatiques Ceased WO2009138349A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200810023885 DE102008023885A1 (de) 2008-05-16 2008-05-16 Funktionalisierte hochvinylaromaten-haltige Dienkautschuke
DE102008023885.6 2008-05-16

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WO2009138349A1 true WO2009138349A1 (fr) 2009-11-19

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AR (1) AR071625A1 (fr)
DE (1) DE102008023885A1 (fr)
TW (1) TW201011048A (fr)
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US9593228B2 (en) 2009-05-27 2017-03-14 Arlanxeo Deutschland Gmbh Mixtures composed of functionalized diene rubbers with trimethylolpropane and fatty acid, a process for production thereof and use thereof

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Publication number Priority date Publication date Assignee Title
DE102008052116A1 (de) 2008-10-20 2010-04-22 Lanxess Deutschland Gmbh Kautschukmischungen mit funktionalisierten Dienkautschuken und Mikrogelen, ein Verfahren zur Herstellung und deren Verwendung
DE102009005713A1 (de) 2009-01-22 2010-07-29 Lanxess Deutschland Gmbh Silanhaltige Kautschukmischungen mit gegebenenfalls funktionalisierten Dienkautschuken und Mikrogelen, ein Verfahren zur Herstellung und deren Verwendung

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DE10049964A1 (de) * 2000-10-10 2002-04-11 Bayer Ag Haftmischungen aus hydroxyl- oder carboxylgruppenhaltigen Lösungskautschuken
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