EP4359227A1 - Kautschukzusammensetzung - Google Patents

Kautschukzusammensetzung

Info

Publication number
EP4359227A1
EP4359227A1 EP22744272.0A EP22744272A EP4359227A1 EP 4359227 A1 EP4359227 A1 EP 4359227A1 EP 22744272 A EP22744272 A EP 22744272A EP 4359227 A1 EP4359227 A1 EP 4359227A1
Authority
EP
European Patent Office
Prior art keywords
rubber composition
phr
carbon atoms
composition according
group
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.)
Pending
Application number
EP22744272.0A
Other languages
English (en)
French (fr)
Inventor
Salvatore Pagano
Stéphanie LAUBE
Flora DESCOMBES
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.)
Compagnie Generale des Etablissements Michelin SCA
Original Assignee
Compagnie Generale des Etablissements Michelin SCA
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 Compagnie Generale des Etablissements Michelin SCA filed Critical Compagnie Generale des Etablissements Michelin SCA
Publication of EP4359227A1 publication Critical patent/EP4359227A1/de
Pending legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
    • B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
    • 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
    • C08K3/02—Elements
    • C08K3/06—Sulfur
    • 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
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • 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
    • C08K5/005—Stabilisers against oxidation, heat, light, ozone

Definitions

  • the field of the present invention is that of rubber compositions, the rubber compositions being particularly intended for use in rubber articles such as, for example, tires.
  • Rubber articles are sensitive to oxidation, in particular during their aging, and require protection systems against this oxidation. Certain antioxidants exist and are used by those skilled in the art.
  • antioxidants which may be of natural origin so as to limit the compounds of fossil origin in rubber articles, and in particular in tires.
  • eugenol or a derivative of eugenol in a rubber composition comprising a diene elastomer, a reinforcing filler and a crosslinking system, makes it possible to protect this composition against oxidation and thus to improve the properties of this composition after ageing.
  • a first object of the invention is a rubber composition based on at least one diene elastomer, a reinforcing filler, a crosslinking system and a phenolic antioxidant of general formula (I) below, in which the radical RI represents a hydrogen atom, an alkyl group comprising from 1 to 18 carbon atoms, or an alkoxy group comprising from 1 to 18 carbon atoms, and the radicals R2 to R7 each represent, independently of each other, an atom of hydrogen or a hydrocarbon group comprising from 1 to 18 carbon atoms.
  • Another object of the invention is a pneumatic or non-pneumatic tire comprising a composition according to the invention.
  • composition based on means a composition comprising the mixture and/or the in situ reaction product of the various constituents used, some of these constituents being able to react and/or being intended to react with one another, less partially, during the various phases of manufacture of the composition; the composition thus possibly being in the totally or partially crosslinked state or in the non-crosslinked state.
  • part by weight per hundred parts by weight of elastomer (or phr) is meant within the meaning of the present invention, the part, by mass per hundred parts by mass of elastomer.
  • any interval of values denoted by the expression “between a and b” represents the domain of values going from more than a to less than b (i.e. limits a and b excluded) while any interval of values denoted by the expression “from a to b” signifies the range of values going from a to b (that is to say including the strict limits a and b).
  • the interval represented by the expression “between a and b” is also and preferably designated.
  • a predominant elastomer is the elastomer representing the greatest mass relative to the total mass of the elastomers in the composition.
  • a so-called majority filler is the one representing the greatest mass among the fillers of the composition.
  • a "minority” compound is a compound which does not represent the largest mass fraction among compounds of the same type.
  • by majority is meant present at more than 50%, preferably more than 60%, 70%, 80%, 90%, and more preferably the “majority” compound represents 100%.
  • the compounds mentioned in the description can be of fossil origin or biosourced. In the latter case, they can be, partially or totally, derived from biomass or obtained from renewable raw materials derived from biomass. In the same way, the compounds mentioned can also come from the recycling of materials already used, that is to say they can be, partially or totally, from a recycling process, or obtained from raw materials themselves resulting from a recycling process. This concerns in particular polymers, plasticizers, fillers, etc.
  • glass transition temperature “Tg” values described herein are measured in a known manner by DSC (Differential Scanning Calorimetry) according to standard ASTM D3418 (1999).
  • iene elastomer or indistinctly rubber, whether natural or synthetic, must be understood in a known manner an elastomer consisting at least in part (i.e., a homopolymer or a copolymer) of diene monomer units (monomers carrying two carbon-carbon double bonds, conjugated or not).
  • diene elastomer capable of being used in the compositions in accordance with the invention is meant in particular:
  • the other monomer can be ethylene, an olefin or a diene, conjugated or not.
  • Suitable conjugated dienes are conjugated dienes having from 4 to 15 carbon atoms, in particular 1,3-dienes, such as in particular 1,3-butadiene and isoprene.
  • Suitable non-conjugated dienes are non-conjugated dienes having 6 to 12 carbon atoms, such as 1,4-hexadiene, ethylidene norbornene, dicyclopentadiene.
  • Suitable olefins are vinylaromatic compounds having 8 to 20 carbon atoms and aliphatic ⁇ -monoolefins having 3 to 12 carbon atoms.
  • Suitable vinyl aromatic compounds are, for example, styrene, ortho-, meta-, para-methylstyrene, the commercial "vinyl-toluene” mixture, para-tert-butylstyrene.
  • Suitable aliphatic ⁇ -monoolefins are in particular acyclic aliphatic ⁇ -monoolefins having from 3 to 18 carbon atoms.
  • the diene elastomer is: (a') - any homopolymer of a conjugated diene monomer, in particular any homopolymer obtained by polymerization of a conjugated diene monomer having from 4 to 12 carbon atoms;
  • the diene elastomer is chosen from the group consisting of polybutadienes (BR), natural rubber (NR), synthetic polyisoprenes (IR), butadiene copolymers, isoprene copolymers, and mixtures of these elastomers.
  • Butadiene copolymers are particularly chosen from the group consisting of butadiene-styrene (SBR) copolymers.
  • the diene elastomer can be modified, that is to say either coupled and/or star-shaped, or functionalized, or coupled and/or star-shaped and simultaneously functionalized.
  • the diene elastomer can be coupled and/or starred, for example by means of a silicon or tin atom which binds the elastomer chains together.
  • the diene elastomer can be simultaneously or alternately functionalized and comprise at least one functional group.
  • functional group is meant a group comprising at least one heteroatom chosen from Si, N, S, O, P.
  • Particularly suitable as functional groups are those comprising at least one function such as: silanol, an alkoxysilane, a primary amine , secondary or tertiary, cyclic or not, a thiol, an epoxide.
  • the rubber composition of the invention may contain a single diene elastomer or a mixture of several diene elastomers.
  • the rubber composition is based on at least one phenolic antioxidant of general formula (I) below,
  • the RI radical represents a hydrogen atom, an alkyl group comprising from 1 to 18 carbon atoms, or an alkoxy group comprising from 1 to 18 carbon atoms,
  • radicals R2 to R7 each independently represent a hydrogen atom or a hydrocarbon group comprising from 1 to 18 carbon atoms.
  • the RI group is a hydrogen atom, a methyl, ethyl, isopropyl, tert-butyl or methoxy group.
  • the radicals R2 to R7 each independently represent a hydrogen atom, an alkyl group comprising from 1 to 18 carbon atoms, or an aryl group comprising from 6 to 18 carbon atoms. More preferably, the radicals R2 to R7 each independently represent a hydrogen atom, a methyl, ethyl, isopropyl or tert-butyl group.
  • the phenolic antioxidant of general formula (I) is eugenol of formula (II) below.
  • the phenolic antioxidant of general formula (I) is present in the composition at a rate comprised in a range ranging from 0.2 to 10 phr, preferably from 0.5 to 8 phr and more preferably from 0.8 to 5 phr.
  • the rubber composition in accordance with the invention has the other essential characteristic of comprising a reinforcing filler.
  • reinforcing filler known for its ability to reinforce a rubber composition that can be used in particular for the manufacture of tires, for example an organic filler such as carbon black, an inorganic filler such as silica or else a mixture of these two types of fillers.
  • Suitable carbon blacks are all carbon blacks, in particular the blacks conventionally used in tires or their treads. Among the latter, mention will be made more particularly of the reinforcing carbon blacks of the 100, 200, 300 series, or the blacks of the 500, 600 or 700 series (ASTM D-1765-2017 grades), such as for example the blacks N115, N134, N234, N326, N330, N339, N347, N375, N550, N683, N772). These carbon blacks can be used in the isolated state, as commercially available, or in any other form, for example as a carrier for some of the rubber additives used. The carbon blacks could for example already be incorporated into the diene elastomer, in particular isoprene in the form of a masterbatch (see for example applications WO97/036724-A2 or WO99/016600-A1).
  • organic fillers other than carbon blacks mention may be made of functionalized polyvinyl organic fillers as described in applications W02006/069792-A1, W02006/069793-A1, W02008/003434-A1 and W02008/003435-A1 .
  • reinforcing inorganic filler should be understood here any inorganic or mineral filler, whatever its color and its origin (natural or synthetic), also called “white” filler, “clear” filler or even “non-black” filler. as opposed to carbon black, capable of reinforcing on its own, with no other means than an intermediate coupling agent, a rubber composition intended for the manufacture of tires.
  • certain reinforcing inorganic fillers can be characterized in particular by the presence of hydroxyl (OH) groups at their surface.
  • Suitable reinforcing inorganic fillers are in particular mineral fillers of the siliceous type, preferably silica (S1O2) or of the aluminous type, in particular alumina (Al2O3).
  • the silica used can be any reinforcing silica known to those skilled in the art, in particular any precipitated or fumed silica having a BET specific surface area as well as a CTAB specific surface area, both of which are less than 450 m 2 /g, preferably comprised in a range ranging from 30 to 400 m 2 /g, in particular from 60 to 300 m 2 /g.
  • non-HDS silica the following commercial silicas can be used: “Ultrasil ® VN2GR” and “Ultrasil ® VN3GR” silicas from Evonik, “Zeosil ® 175GR” silica from Solvay, "Hi -Sil EZ120G(-D)", “Hi-Sil EZ160G(-D)”, “Hi-Sil EZ200G(-D)”, “Hi-Sil 243LD”, “Hi-Sil 210", “Hi-Sil HDP 320G” from PPG.
  • inorganic fillers capable of being used in the rubber compositions of the invention
  • mineral fillers of the alumina type in particular alumina (Al2O3), aluminum oxides, aluminum hydroxides, aluminosilicates, titanium oxides, silicon carbides or nitrides, all of the reinforcing type as described for example in applications W099/28376-A2, WOOO/73372-A1, WO02/053634-A1 , W02004/003067-A1, W02004/056915-A2, US6610261-B1 and US6747087-B2.
  • aluminas “Baikalox A125” or “CRI 25” (Ba ⁇ kowski company), “APA-100RDX” (Congrua), “Aluminoxid C” (Evonik) or “AKP-G015” (Sumitomo Chemicals).
  • reinforcing inorganic filler also means mixtures of different reinforcing inorganic fillers, in particular of silicas as described above.
  • a reinforcing filler of another nature could be used, since this reinforcing filler of another nature would be covered with an inorganic layer.
  • an inorganic layer such as silica, or would comprise functional sites on its surface, in particular hydroxyls, requiring the use of a coupling agent to establish the bond between this reinforcing filler and diene elastomer.
  • the reinforcing filler is chosen from the group consisting of carbon blacks, silicas and mixtures thereof.
  • this content of total reinforcing filler is within a range ranging from 10 to 200 phr, more preferably from 30 to 180 phr, and even more preferably from 40 to 160 phr; the optimum being in known manner different according to the particular applications targeted.
  • BET surface area is determined by gas adsorption using the Brunauer-Emmett-Teller method described in "The Journal of the American Chemical Society” (Vol. 60, page 309, February 1938) , and more precisely according to a method adapted from standard NF ISO 5794-1, appendix E of June 2010 [multipoint volumetric method (5 points) - gas: nitrogen - vacuum degassing: one hour at 160°C - relative pressure range p/in: 0.05 to 0.17]
  • CT AB specific surface values were determined according to standard NF ISO 5794-1, appendix G of June 2010. The process is based on the adsorption of CT AB (bromide of N -hexadecyl-N,N,N-trimethylammonium) on the "external" surface of the reinforcing filler.
  • an at least bifunctional coupling agent intended to ensure a sufficient connection, of a chemical and/or physical nature, between the inorganic filler ( surface of its particles) and diene elastomer.
  • at least bifunctional organosilanes or polyorganosiloxanes are used.
  • bifunctional is meant a compound having a first functional group capable of interacting with the inorganic filler and a second functional group capable of interacting with the diene elastomer.
  • such a bifunctional compound may comprise a first functional group comprising a silicon atom, said first functional group being capable of interacting with the hydroxyl groups of an inorganic filler and a second group functional comprising a sulfur atom, said second functional group being able to interact with the diene elastomer.
  • the organosilanes are chosen from the group consisting of polysulphide organosilanes (symmetrical or asymmetrical) such as bis(3-triethoxysilylpropyl) tetrasulphide, abbreviated as TESPT marketed under the name “Si69” by the company Evonik or bis disulphide -(triethoxysilylpropyl), abbreviated as TESPD marketed under the name "Si75” by the company Evonik, polyorganosiloxanes, mercaptosilanes, blocked mercaptosilanes, such as S-(3-(triethoxysilyl)propyl) octanethioate marketed by the company Momentive under the name “NXT Silane”. More preferably, the organosilane is a polysulphide organosilane.
  • the content of coupling agent in the composition of the invention is advantageously less than or equal to 30 phr, it being understood that it is generally desirable to use as little as possible.
  • the rate of coupling agent represents from 0.5% to 15% by weight relative to the amount of reinforcing inorganic filler. Its content is preferably within a range ranging from 0.5 to 20 phr, more preferably within a range ranging from 3 to 3 phr. This rate is easily adjusted by those skilled in the art according to the rate of reinforcing inorganic filler used in the composition of the invention.
  • the crosslinking system can be any type of system known to those skilled in the art in the field of rubber compositions for tires. It may in particular be based on sulfur, and/or peroxide and/or bismaleimides.
  • the crosslinking system is sulfur-based, one then speaks of a vulcanization system.
  • the sulfur can be provided in any form, in particular in the form of molecular sulfur, or of a sulfur-donating agent.
  • At least one vulcanization accelerator is also preferentially present, and, optionally, also preferentially, various known vulcanization activators such as zinc oxide, stearic acid or equivalent compound such as stearic acid salts and salts can be used. of transition metals, guanidine derivatives (in particular diphenylguanidine), or alternatively known vulcanization retarders.
  • the sulfur is used at a preferential rate of between 0.2 phr and 10 phr, more preferentially between 0.3 and 7 phr.
  • the primary vulcanization accelerator is used at a preferential rate comprised between 0.5 and 10 phr, more preferentially comprised between 0.5 and 5 phr.
  • Any compound capable of acting as a vulcanization accelerator for diene elastomers in the presence of sulfur can be used as an accelerator, in particular accelerators of the thiazole type as well as their derivatives, accelerators of the sulfenamide, thiuram, dithiocarbamate, dithiophosphate, thiourea and xanthate type.
  • MBTS 2-mercaptobenzothiazyl disulphide
  • CBS N-cyclohexyl-2-benzothiazyl sulfenamide
  • DCBS N,N-dicyclohexyl- 2-Benzothiazyl sulfenamide
  • TBBS N-ter-butyl-2-benzothiazyl sulfenamide
  • TZTD tetrabenzylthiuram disulfide
  • ZBEC zinc dibenzyldithiocarbamate
  • the rubber compositions according to the invention may also optionally comprise all or part of the usual additives usually used in elastomer compositions for tires, such as, for example, pigments, protective agents such as anti-ozone waxes, anti-ozonants chemicals, antioxidants other than the phenolic antioxidant of general formula (I), anti-fatigue agents, or even reinforcing resins (as described for example in application WO 02/010269).
  • additives usually used in elastomer compositions for tires such as, for example, pigments, protective agents such as anti-ozone waxes, anti-ozonants chemicals, antioxidants other than the phenolic antioxidant of general formula (I), anti-fatigue agents, or even reinforcing resins (as described for example in application WO 02/010269).
  • compositions in accordance with the invention can be manufactured in suitable mixers, using two successive preparation phases well known to those skilled in the art:
  • thermomechanical mixing (so-called "non-productive" phase), which can be carried out in a single thermomechanical step during which, in a suitable mixer such as a usual internal mixer (for example 'Banbury' type), all the necessary constituents, in particular the elastomeric matrix, the reinforcing filler, any other miscellaneous additives, with the exception of the crosslinking system.
  • a suitable mixer such as a usual internal mixer (for example 'Banbury' type)
  • all the necessary constituents in particular the elastomeric matrix, the reinforcing filler, any other miscellaneous additives, with the exception of the crosslinking system.
  • the incorporation of the optional filler into the elastomer can be carried out in one or more stages by mixing thermomechanically.
  • the filler is already incorporated in whole or in part into the elastomer in the form of a masterbatch (“masterbatch” in English) as described for example in applications WO 97/036724 or WO 99/016600, it is the masterbatch which is mixed directly and, where appropriate, the other elastomers or fillers present in the composition which are not in the form of the masterbatch, as well as any other miscellaneous additives other than the crosslinking system, are incorporated.
  • the non-productive phase can be carried out at high temperature, up to a maximum temperature of between 110° C. and 200° C., preferably between 130° C. and 185° C., for a duration generally of between 2 and 10 minutes.
  • a second phase of mechanical work (so-called "productive" phase), which is carried out in an external mixer such as a roller mixer, after cooling the mixture obtained during the first non-productive phase to a lower temperature, typically below 120° C., for example between 40° C. and 100° C.
  • the crosslinking system is then incorporated, and the whole is then mixed for a few minutes, for example between 5 and 15 min.
  • the final composition thus obtained is then calendered, for example in the form of a sheet or a plate, in particular for characterization in the laboratory, or else extruded (or co-extruded with another rubber composition) in the form of a semi-finished (or profiled) rubber that can be used, for example, as a tire sidewall.
  • extruded or co-extruded with another rubber composition
  • a semi-finished (or profiled) rubber that can be used, for example, as a tire sidewall.
  • the composition can be either in the green state (before crosslinking or vulcanization), or in the cured state (after crosslinking or vulcanization), can be a semi-finished product which can be used in a tire.
  • the crosslinking (or curing), where appropriate the vulcanization, is carried out in a known manner at a temperature generally between 130° C. and 200° C., for a sufficient time which can vary for example between 5 and 90 min depending in particular on the curing temperature, the crosslinking system adopted and the crosslinking kinetics of the composition considered.
  • a temperature generally between 130° C. and 200° C., for a sufficient time which can vary for example between 5 and 90 min depending in particular on the curing temperature, the crosslinking system adopted and the crosslinking kinetics of the composition considered. 11-7 Rubber articles
  • a subject of the present invention is also a rubber article comprising a rubber composition according to the invention.
  • the interest presented by the properties of the rubber composition according to the invention makes it possible to envisage a use in the numerous fields involving rubber articles. Mention may in particular be made of a use in various articles preferably chosen from pipes, belts, conveyor belts, caterpillars, pneumatic objects (and in particular tires), shoe soles, or even surgical gloves.
  • the invention relates to a tire comprising a composition according to the invention.
  • the tire according to the invention can be intended to equip motor vehicles of the passenger car type, SUV ("Sport Utility Vehicles"), or two wheels (in particular motorcycles), or airplanes, or even industrial vehicles chosen from vans, "Weight -heavy” - i.e. metro, bus, road transport vehicles (trucks, tractors, trailers), off-road vehicles such as agricultural or civil engineering machinery -, and others.
  • T0 corresponds to the case where the polymer is completely devoid of antioxidant system.
  • T1 is a control in which the polymer is protected by a known phenolic antioxidant: G “Irganox 1520 L” marketed by the company BASF.
  • Composition C1 illustrates the present invention and contains the polymer, protected against oxidation by eugenol, in an isomolar quantity of 3.2 phr of “Irganox 1520 L”.
  • Table 1 presents the compositions tested (in phr), the results obtained.
  • Example 2 The purpose of Example 2 is to measure the aging resistance performance of the invention subjected to a thermo-oxidative treatment by comparing a composition in accordance with the invention (C2), respectively with two control compositions (T2 and T3).
  • the rubber compositions were produced as described in point 11.6 above, using an internal mixer (non-productive phase) where most of the ingredients are incorporated.
  • the so-called productive phase is carried out on an external tool and concerns the incorporation of the sulfur and the accelerator.
  • the various compositions were shaped, vulcanized in sheet form and subjected to a thermo-oxidizing treatment at 77° C. for 0, 7, 14, 21 and 28 days. For each of these points, the properties at break are characterized by uniaxial tensile measurements (modulus, elongation). Limit properties, modulus and elongation at break
  • Table 3 presents the compositions tested (in phr), and Table 4 presents the results obtained, in base 100.
  • Table 3 presents the compositions tested (in phr), and Table 4 presents the results obtained, in base 100.

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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)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
EP22744272.0A 2021-06-25 2022-06-24 Kautschukzusammensetzung Pending EP4359227A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR2106816A FR3124512A1 (fr) 2021-06-25 2021-06-25 Composition de caoutchouc
PCT/FR2022/051252 WO2022269208A1 (fr) 2021-06-25 2022-06-24 Composition de caoutchouc

Publications (1)

Publication Number Publication Date
EP4359227A1 true EP4359227A1 (de) 2024-05-01

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP22744272.0A Pending EP4359227A1 (de) 2021-06-25 2022-06-24 Kautschukzusammensetzung

Country Status (3)

Country Link
EP (1) EP4359227A1 (de)
FR (1) FR3124512A1 (de)
WO (1) WO2022269208A1 (de)

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FR2903416B1 (fr) 2006-07-06 2008-09-05 Michelin Soc Tech Composition elastomerique renforcee d'une charge de polymere vinylique non aromatique fonctionnalise
EP4045334A1 (de) * 2019-10-15 2022-08-24 Rhodia Operations Verfahren zur herstellung von modifiziertem silica, modifiziertes silica und dessen verwendungen

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