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WO2016002967A1 - Pneu présentant une bande de roulement comprenant des particules de liège - Google Patents

Pneu présentant une bande de roulement comprenant des particules de liège Download PDF

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Publication number
WO2016002967A1
WO2016002967A1 PCT/JP2015/069369 JP2015069369W WO2016002967A1 WO 2016002967 A1 WO2016002967 A1 WO 2016002967A1 JP 2015069369 W JP2015069369 W JP 2015069369W WO 2016002967 A1 WO2016002967 A1 WO 2016002967A1
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WO
WIPO (PCT)
Prior art keywords
phr
tire according
particles
tire
butadiene
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Application number
PCT/JP2015/069369
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English (en)
Inventor
Boyong XUE
Salvatore Pagano
Michael Edward Dotson
Original Assignee
Compagnie Generale Des Etablissements Michelin
Michelin Recherche Et Technique S.A.
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, Michelin Recherche Et Technique S.A. filed Critical Compagnie Generale Des Etablissements Michelin
Priority to JP2016575249A priority Critical patent/JP6647227B2/ja
Publication of WO2016002967A1 publication Critical patent/WO2016002967A1/fr

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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
    • C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
    • 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
    • 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
    • B60C1/0016—Compositions of the tread
    • 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
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • 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
    • 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
    • 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
    • C08K5/0016—Plasticisers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L7/00—Compositions of natural rubber
    • 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
    • C08L9/06—Copolymers with styrene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L97/00—Compositions of lignin-containing materials
    • C08L97/007—Cork
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/14—Polymer mixtures characterised by other features containing polymeric additives characterised by shape
    • C08L2205/18—Spheres

Definitions

  • the present invention relates to rubber compositions forming treads of tires, the tires and to a process manufacturing the tires. It relates more particularly to the tires having the treads that comprise the rubber compositions capable to reduce noise from the tires when the vehicle is moving.
  • Rl 17-02 The World Forum for Harmonization of Vehicle Regulations in UN/ECE (WP.29) adopted the revision 2 (called Rl 17-02 below) in 2010. Limits in Rl 17-02 are more severe than that in Rl 17-01 by about 4 dB(A). Rl 17-02 has been implemented in Europe since 2012 and several countries and zones are going to ratify Rl 17-02. Therefore, there is a constant compelling need for reducing the tire rolling noise emission (called coast-by noise below) in the worldwide.
  • solid-route transmission which is generally dominant for the low frequencies of the spectrum (up to about 400 HZ);
  • aerial-route transmission which is generally dominant in the high frequencies (about 600 HZ and above).
  • the noise known as “road noise” rather makes reference to the overall level perceived in the vehicle and over a frequency range of up to 2000 HZ.
  • the noise known as “cavity noise” refers to the nuisance caused by the resonance of the inflation cavity of the tire casing.
  • noise emitted outside the vehicle various interactions between the tire and the road surfacing and between the tire and the air are pertinent, and will be a nuisance to people in the vicinity of the vehicle when it is rolling on a road.
  • several sources of noise are also distinguished, such as the "indentation” noise due to the impact of the unevenness of the road in the area of contact, the “friction” noise essentially generated on leaving the area of contact, the “profile” noise due to the arrangement of the profile elements and to the resonance in the various grooves.
  • the specific range of frequencies concerned by these outside noises corresponds herein typically to a range of from 300 to 3000 HZ approximately.
  • the objective of the invention is to provide a tire having treads that can reduce the coast-by noise, while at least maintaining or even improving the stability performance.
  • a first subject matter of the present invention is a tire, in an unvulcanized state or a vulcanized one, having a tread that comprises a rubber composition comprising at least, a diene elastomer, 20 to 100 phr of a plasticizer chosen from the group consisting of liquid plasticizers, hydrocarbon resins and the mixtures thereof, 20 to
  • the median size by weight of said particles is more than 0.5 mm and less than 3 mm and the density of the rubber composition is from 0.55 to 0.96 g/cm 3 .
  • aspects of the present invention can be as follows.
  • plasticizer chosen from the group consisting of liquid plasticizers, hydrocarbon resins and the mixtures thereof;
  • the median size by weight of said particles is more than 0.5 mm and less than 3 mm and the density of the rubber composition is from 0.55 to 0.96 g/cm 3 .
  • diene elastomer is chosen from the group consisting of natural rubber, synthetic polyisoprenes, polybutadienes, butadiene copolymers, isoprene copolymers and the mixtures thereof.
  • polyisoprenes polyisoprenes, isoprene copolymers, and mixtures thereof.
  • polyisoprenes polybutadienes having a content of cis-1,4 bonds of greater than 90%, and mixtures thereof.
  • the plasticizer comprises liquid plasticizers chosen from the group consisting of polyolefinic oils, naphthenic oils, paraffinic oils, Distillate Aromatic Extracts (DAE) oils, Medium Extracted Solvates (MES) oils, Treated Distillate Aromatic Extracts (TDAE) oils, Residual Aromatic Extracts (RAE) oils, Treated Residual Aromatic Extracts (TRAE) oils, Safety Residual Aromatic Extracts (SRAE) oils, mineral oils, vegetable oils, ether plasticizers, ester plasticizers, phosphate plasticizers, sulphonate plasticizers and the mixtures thereof.
  • liquid plasticizers chosen from the group consisting of polyolefinic oils, naphthenic oils, paraffinic oils, Distillate Aromatic Extracts (DAE) oils, Medium Extracted Solvates (MES) oils, Treated Distillate Aromatic Extracts (TDAE) oils, Residual Aromatic Extracts (RAE) oils, Treated Residual Aromatic Extracts (TRAE)
  • the plasticizer comprises hydrocarbon resins chosen from the group consisting of cyclopentadiene homopolymer or copolymer resins, dicyclopentadiene homopolymer or copolymer resins, terpene homopolymer or copolymer resins, C5 fraction homopolymer or copolymer resins, C9 fraction homopolymer or copolymer resins, alpha-methyl styrene homopolymer or copolymer resins, and the mixtures of these resins.
  • hydrocarbon resins chosen from the group consisting of cyclopentadiene homopolymer or copolymer resins, dicyclopentadiene homopolymer or copolymer resins, terpene homopolymer or copolymer resins, C5 fraction homopolymer or copolymer resins, C9 fraction homopolymer or copolymer resins, alpha-methyl styrene homopolymer or copolymer resins, and the mixtures of
  • a plasticizer chosen from the group consisting of liquid plasticizers, hydrocarbon resins and the mixtures thereof
  • particles of cork More than 15 phr and less than 100 phr of particles of cork, said particles having a median size by weight of between 0.7 and 4 mm;
  • thermomechanically in one or more goes, until a maximum temperature of between 130° C and 200° C reached;
  • a rubber composition comprising at least:
  • plasticizer chosen from the group consisting of liquid plasticizers, hydrocarbon resins and the mixtures thereof;
  • the median size by weight of said particles is more than 0.5 mm and less than 3 mm and the density of the rubber composition is from 0.55 to 0.96 g/cm 3 .
  • the tires of the present invention are particularly intended to equip passenger motor vehicles, including 4x4 (four-wheel drive or all-wheel drive) vehicles and SUV (Sport Utility Vehicles) vehicles, two-wheel vehicles (in particular motorcycles), and also industrial vehicles in particular chosen from vans and heavy-duty vehicles (i.e., underground vehicles, bus vehicles or heavy road transport vehicles (lorries, tractors, trailers)), or off-road vehicles, such as agricultural vehicles or earthmoving equipment.
  • 4x4 four-wheel drive or all-wheel drive
  • SUV Sport Utility Vehicles
  • two-wheel vehicles in particular motorcycles
  • industrial vehicles in particular chosen from vans and heavy-duty vehicles (i.e., underground vehicles, bus vehicles or heavy road transport vehicles (lorries, tractors, trailers)), or off-road vehicles, such as agricultural vehicles or earthmoving equipment.
  • the machine rolling test was performed by placing in contact (each tire under an inflation pressure (180 kPa) of the tire mounted on a rim (6.5Jxl6) and subjected to a load (4.25 kN) ) on the outer surface of a cylinder provided with a rough surface.
  • the assembly is placed in a soundproof chamber (semi-anechoic).
  • Several microphones are placed around the contact area to record the sound level during rolling, over a range of frequencies ranging from 500 to 2500 Hz, for a rolling speed (80km/hour).
  • any interval of values denoted by the expression "between a and b” represents the range of values extending from greater than a to less than b (that is to say, limits a and b excluded) whereas any interval of values denoted by the expression “from a to b” means the range of values extending from a up to b (that is to say, including the strict limits a and b).
  • the tread of the tire according to the present invention comprises a rubber composition which has an essential feature of comprising a diene elastomer.
  • iene elastomer or rubber should be understood as meaning an elastomer resulting at least in part (i.e., a homopolymer or a copolymer) from diene monomers (monomers carrying two carbon-carbon double bonds which may or may not be conjugated). [ 0 0 2 1 ]
  • Diene elastomers can be classified in a known way into two categories: those "essentially unsaturated” and those "essentially saturated”.
  • Butyl rubbers such as, for example copolymers of dienes and of -olefins of EPDM type, come within the category of essentially saturated diene elastomers, having a content of units of diene origin which is low or very low, always less than 15% (mol%).
  • essentially unsaturated diene elastomer is understood to mean a diene elastomer resulting at least in part from conjugated diene monomers, having a content of units of diene origin (conjugated dienes) which is greater than 15% (mol%).
  • highly unsaturated diene elastomer is understood to mean in particular a diene elastomer having a content of units of diene origin (conjugated dienes) which is greater than 50%.
  • At least one diene elastomer of the highly unsaturated type in particular a diene elastomer chosen from the group consisting of polybutadienes (BR), synthetic polyisoprenes (IR), natural rubber (NR), butadiene copolymers, isoprene copolymers and mixtures of these elastomers.
  • a diene elastomer chosen from the group consisting of polybutadienes (BR), synthetic polyisoprenes (IR), natural rubber (NR), butadiene copolymers, isoprene copolymers and mixtures of these elastomers.
  • Such copolymers are more preferably chosen from the group consisting of butadiene/styrene copolymers (SBR), isoprene/butadiene copolymers (BIR), isoprene/styrene copolymers (SIR), isoprene/butadiene/styrene copolymers (SBIR) and mixtures of such copolymers.
  • SBR butadiene/styrene copolymers
  • BIR isoprene/butadiene copolymers
  • SIR isoprene/styrene copolymers
  • SBIR isoprene/butadiene/styrene copolymers
  • the rubber composition composing the tread of the tire of the present invention comprises, as the diene elastomer, from 50 to 100 phr of a copolymer based on styrene and on butadiene, that is to say a copolymer of at least one styrene monomer and of at least one butadiene monomer; in other words, said copolymer based on styrene and on butadiene comprises, by definition, at least units derived from styrene and units derived from butadiene.
  • the content of said copolymer in the rubber composition is within a range from 50 to 90 phr, particularly within a range from 60 to 85 phr.
  • Suitable butadiene monomers are in particular 1,3 -butadiene, 2-methyl- 1,3 -butadiene, 2,3-di(Cl-C5 alkyl)-l,3-butadienes such as for example 2,3-dimethyl-l,3-butadiene, 2,3-diethyl-l,3-butadiene, 2-methyl-3 -ethyl- 1,3 -butadiene or 2-methyl-3-isopropyl- 1,3-butadiene and an aryl-l,3-butadiene.
  • Suitable styrene monomers are in particular styrene, methylstyrenes, para-(tert-butyl)styrene, methoxystyrenes and chlorostyrenes.
  • Said copolymer based on styrene and on butadiene may have any microstructure, which is a function of the polymerization conditions used, in particular of the presence or absence of a modifying and/or randomizing agent and of the amounts of modifying and/or randomizing agents used. It may be, for example, a block, statistical, sequential or microsequential copolymer, and may be prepared in dispersion or in solution; it may be coupled and/or star-branched or else functionalized with a coupling and/or star-branching or functionalizing agent.
  • the copolymer based on styrene and on butadiene is chosen from the group consisting of styrene-butadiene (abbreviated to SBR) copolymers, styrene- butadiene-isoprene (abbreviated to SBIR) copolymers and blends of such copolymers.
  • SBR styrene-butadiene
  • SBIR styrene-butadiene-isoprene
  • SBIR copolymers mention may especially be made of those having a styrene content between 5% and 50% by weight and more particularly between 10% and 40%, an isoprene content between 15% and 60% by weight and more particularly between 20% and 50%, a butadiene content between 5% and 50% by weight and more particularly between 20% and 40%, a content (mol%) of 1 ,2- units of the butadiene part of between 4%» and 85%, a content (mol%) of trans- 1,4- units of the butadiene part of between 6% and 80%, a content (mol%) of 1,2- units plus 3,4- units of the isoprene part of between 5% and 70% and a content (mol%) of trans- 1,4- units of the isoprene part of between 10% and 50%.
  • an SBR copolymer is used.
  • SBR copolymers mention may especially be made of those having a styrene content of between 5%» and 60% by weight and more particularly of between 20% and 50%, a content (mol%) of 1 ,2- bonds of the butadiene part of between 4% and 75% and a content (mol%) of trans- 1,4- bonds of between 10% and 80%.
  • the Tg (glass transition temperature) of copolymer based on styrene and on butadiene is preferably greater than -40°C, more preferably greater than -35°C, particularly within a range from -30°C to +30°C, more particularly within a range from -25°C to +25°C. [ 0 0 3 1 ]
  • Tg of the elastomers described here is measured in a conventional manner, well known to a person skilled in the art, on an elastomer in the dry state (i.e. without extender oil) and by DSC ⁇ Differential Scanning Calorimetry) (for example according to ASTM D3418 (1999)).
  • a person skilled in the art knows how to modify the microstructure of a copolymer based on styrene and on butadiene, in particular of an SBR, in order to increase and adjust its Tg, especially by playing with the contents of styrene, of 1,2- bonds or else of trans-1,4- bonds of the butadiene part.
  • Use is more preferably made of an SBR (solution or emulsion) having a styrene content (mol%) which is greater than 35%, more particularly between 35% and 60%, in particular within a range from 38% to 50%.
  • SBRs having a relatively high Tg are well known to a person skilled in the art; they have been used in particular in tire treads for improving some of their standard properties.
  • At least another optional (or second) diene elastomer, optional and different from said copolymer i.e. not comprising units derived from styrene and butadiene
  • said second diene elastomer being present in a weight content which is consequently at most equal to 50 phr in case of that content of copolymer based on styrene and on butadiene is at least equal to 50 phr. That means content of the other diene elastomer(s) is 100 phr minus that of copolymer based on styrene and on butadiene. [ 0 0 3 4 ]
  • This optional second diene elastomer is preferably chosen from the group consisting of natural rubbers (NR), synthetic polyisoprenes (IR), polybutadienes (BR), isoprene copolymers and blends of these elastomers.
  • Such copolymers are more preferably chosen from the group consisting of isoprene-butadiene copolymers (BIR) and isoprene-styrene copolymers (SIR).
  • polybutadiene (BR) homopolymers and in particular those having a content (mol%) of 1,2- units of between 4% and 80% or those having a content (mol%) of cis-1,4- units of greater than 80%; polyisoprene (IR) homopolymers; butadiene-isoprene copolymers (BIR) and especially those having an isoprene content of between 5% and 90% by weight and a Tg from -40°C to -80°C; and isoprene-styrene copolymers (SIR) and especially those having a styrene content of between 5% and 50% by weight and a Tg of between -25 °C and - 50°C.
  • BR polybutadiene
  • IR polyisoprene
  • BIR butadiene-isoprene copolymers
  • SIR isoprene-styrene copolymers
  • the second diene elastomer is an isoprene elastomer, more preferably natural rubber or a synthetic polyisoprene of cis-1,4- type; among these synthetic polyisoprenes, use is preferably made of polyisoprenes having a content (mol%) of cis-1,4- bonds of greater than 90%, more preferably still of greater than 98%.
  • the second diene elastomer is a polybutadiene, preferably a polybutadiene having a content (mol%) of cis-1,4 bonds of greater than 90%.
  • the second diene elastomer is a mixture of polybutadiene with the following isoprene elastomer (natural rubber or synthetic polyisoprene).
  • the rubber composition of the tread of the tire according to the present invention comprises a plasticizer chosen from the group consisting of liquid plasticizers, (solid) hydrocarbon resins and the mixtures thereof, within a range from 20 to 100 phr.
  • Liquid plasticizers are liquid at 20°C by definition , their role is to soften the matrix by diluting the elastomer and the reinforcing filler; their Tg is by definition less than -20°C, preferably less than -40°C.
  • any extending oil whether of aromatic or non-aromatic nature, any liquid plasticizing agent known for its plasticizing properties with regard to diene elastomers, can be used.
  • these plasticizers or these oils which are more or less viscous, are liquids (that is to say, as a reminder, substances that have the ability to eventually take on the shape of their container), as opposed, in particular, to plasticizing hydrocarbon resins which are by nature solid at ambient temperature.
  • Liquid plasticizers chosen from the group consisting of polyolefinic oils, naphthenic oils (low or high viscosity, in particular hydrogenated or otherwise), paraffinic oils, DAE (Distillate Aromatic Extracts) oils, MES (Medium Extracted Solvates) oils, TDAE oils (Treated Distillate Aromatic Extracts), RAE oils (Residual Aromatic Extracts), TRAE oils (Treated Residual Aromatic Extracts), SRAE oils (Safety Residual Aromatic Extracts), mineral oils, vegetable oils, ether plasticizers, ester plasticizers, phosphate plasticizers, sulphonate plasticizers and the mixtures thereof are particularly suitable.
  • the liquid plasticizer is chosen from the group consisting of MES oils, TDAE oils, naphthenic oils, vegetable oils and the mixtures thereof.
  • phosphate plasticizers for example, of those that contain between 12 and 30 carbon atoms, for example trioctyl phosphate.
  • ester plasticizers mention may especially be made of the compounds chosen from the group consisting of trimellitates, pyromellitates, phthalates, 1 ,2-cyclohexane dicarboxylates, adipates, azelates, sebacates, triesters of glycerol, and mixtures thereof.
  • glycerol triesters preferably composed predominantly (for more than 50% by weight, more preferably for more than 80% by weight) of an unsaturated Ci 8 fatty acid, that is to say an unsaturated fatty acid chosen from the group consisting of oleic acid, linoleic acid, linolenic acid and the mixtures thereof. More preferably, whether of synthetic origin or natural origin (in the case, for example, of sunflower or rapeseed vegetable oils), the fatty acid used is composed for more than 50% by weight, more preferably still from 80% by weight, of oleic acid.
  • Such triesters (trioleates) comprising a high content of oleic acid are well known; for example they have been described in Application WO 02/088238, as plasticizing agents in treads for tires.
  • Hydrocarbon resins which are solid plasticizers (at 20°C), exhibit a Tg of greater than +20°C, preferably greater than +30°C, such as is described, for example in Applications WO 2005/087859, WO 2006/061064 and WO 2007/017060.
  • Hydrocarbon resins are polymers well known to a person skilled in the art which are essentially based on carbon and hydrogen and thus miscible by nature in diene elastomer composition(s), when they are additionally described as being “plasticizing". They have been described, for example, in the work entitled “Hydrocarbon Resins” by R. Mildenberg, M. Zander and G. Collin (New York, VCH, 1997, ISBN 3-527-28617-9), chapter 5 of which is devoted to their applications, in particular in the tire rubber field (5.5. "Rubber Tires and Mechanical Goods”). They can be aliphatic or aromatic or also of the aliphatic/aromatic type, that is to say based on aliphatic and/or aromatic monomers.
  • They can be natural or synthetic and may or may not be petroleum-based (if such is the case, also known under the name of petroleum resins). They are preferably exclusively hydrocarbon, that is to say that they comprise only carbon and hydrogen atoms. [ 0 0 4 7 ]
  • the plasticizing hydrocarbon resin exhibits at least one, more preferably all, of the following characteristics:
  • Tg of greater than 20°C (more preferably between 40 and 100°C;
  • Mn number-average molecular weight
  • PI polydispersity index
  • the Tg is measured in a known way by DSC ⁇ Differential Scanning Calorimetry) according to Standard ASTM D3418 (1999).
  • the macrostructure (Mw, Mn and PI) of the hydrocarbon resin is determined by steric exclusion chromatography (SEC): solvent tetrahydrofuran; temperature 35°C; concentration 1 g/1; flow rate 1 ml/min; solution filtered through a filter with a porosity of 0.45 ⁇ before injection; Moore calibration with polystyrene standards; set of 3 "Waters" columns in series (“Styragel” HR4E, HRl and HR0.5); detection by differential refractometer ("Waters 2410") and its associated operating software ("Waters Empower").
  • the plasticizing hydrocarbon resin is chosen from the group consisting of cyclopentadiene (abbreviated to CPD) homopolymer or copolymer resins, dicyclopentadiene (abbreviated to DCPD) homopolymer or copolymer resins, terpene homopolymer or copolymer resins, C 5 fraction homopolymer or copolymer resins, C 9 fraction homopolymer or copolymer resins, alpha-methyl styrene homopolymer or copolymer resins and the mixtures thereof.
  • CPD cyclopentadiene
  • DCPD dicyclopentadiene
  • terpene homopolymer or copolymer resins terpene homopolymer or copolymer resins
  • C 5 fraction homopolymer or copolymer resins C 9 fraction homopolymer or copolymer resins
  • alpha-methyl styrene homopolymer or copolymer resins alpha-methyl
  • Use is more preferably made, among the above copolymer resins, of those chosen from the group consisting of (D)CPD/ vinylaromatic copolymer resins, (D)CPD/terpene copolymer resins, (D)CPD/C fraction copolymer resins, (D)CPD/C 9 fraction copolymer resins, terpene/vinylaromatic copolymer resins, terpene/phenol copolymer resins, C 5 fraction/vinyl-aromatic copolymer resins, C 9 fraction/vinylaromatic copolymer resins, and the mixtures thereof.
  • pene combines here, in a known way, the a-pinene, ⁇ -pinene and limonene monomers; use is preferably made of a limonene monomer, which compound exists, in a known way, in the form of three possible isomers: L-limonene (laevorotatory enantiomer), D-limonene (dextrorotatory enantiomer) or else dipentene, the racemate of the dextrorotatory and laevorotatory enantiomers.
  • Styrene a-methylstyrene, ortho-, meta- or para-methyl styrene, vinyltoluene, para-(tert- butyl)styrene, methoxystyrenes, chlorostyrenes, hydroxystyrenes vinylmesitylene, divinylbenzene, vinylnaphthalene, or any vinylaromatic monomer resulting from a C 9 fraction (or more generally from a C 8 to C 10 fraction) are suitable, for example, as vinylaromatic monomer.
  • the vinylaromatic compound is styrene or a vinylaromatic monomer resulting from a C fraction (or more generally from a C 8 to C 10 fraction).
  • the vinylaromatic compound is the minor monomer, expressed as molar fraction, in the copolymer under consideration.
  • the content of total plasticizing agent is preferably from 20 to 80 phr and more preferably from 25 to 75 phr. 5-3. Reinforcing filler
  • Use may be made of any type of reinforcing filler known for its capabilities of reinforcing a rubber composition which can be used for the manufacture of tires, for example an organic reinforcing filler, such as carbon black, or a reinforcing inorganic filler, such as silica, with which a coupling agent is combined in a known way.
  • an organic reinforcing filler such as carbon black
  • a reinforcing inorganic filler such as silica
  • Such a reinforcing filler typically consists of nanoparticles, the mean size (by weight) (see, for example, ISO- 13320 - Particle size analysis-Laser diffraction methods), of which is less than 500 nm, generally between 20 nm and 200 nm, in particular and preferably between 20 nm and 150 nm.
  • All carbon blacks in particular blacks of the HAF, ISAF or SAF type, conventionally used in treads for tires ("tire-grade” blacks) are suitable as carbon blacks. Mention will more particularly be made, among the latter, of the reinforcing carbon blacks of the 100, 200, 300, 600 or 700 series (ASTM grades), such as, for example, the N115, N134, N234, N326, N330, N339, N347, N375 blacks.
  • the carbon blacks might, for example, be already incorporated in the isoprene elastomer in the form of a masterbatch (see, for example, Applications WO 97/36724 or WO 99/16600).
  • filler should be understood here as meaning any inorganic or mineral filler, whatever its colour and its origin (natural or synthetic), also known as “white filler” or sometimes “clear filler” in contrast to carbon black, capable of reinforcing by itself, without means other than an intermediate coupling agent, a rubber composition intended for the manufacture of tires, in other words capable of replacing, in its reinforcing role, a conventional tire-grade carbon black; such a filler is generally characterized, in a known way, by the presence of hydroxyl (-OH) groups at its surface.
  • -OH hydroxyl
  • Mineral fillers of the siliceous type in particular silica (Si0 2 ), or of the aluminous type, in particular alumina (A1 2 0 3 ), are suitable in particular as reinforcing inorganic fillers.
  • the silica used can be any reinforcing silica known to a person skilled in the art, in particular any precipitated or pyrogenic silica exhibiting a BET surface and a CTAB specific surface both of less than 450 m 2 /g, preferably from 30 to 400 m 2 /g, in particular between 60 and 300 m /g.
  • HD precipitated silicas for example, of the Ultrasil 7000 and Ultrasil 7005 silicas from Evonik, the "Zeosil” 1165MP, 1135MP and 1 1 15MP silicas from Rhodia, the "Hi-Sil” EZ150G silica from PPG, the "Zeopol” 8715, 8745 and 8755 silicas from Huber.
  • the rubber composition of the tread of the tire according to the present invention comprises a reinforcing filler (in particular silica or carbon black or a mixture of silica and carbon black) within a range from 20 to 150 phr.
  • a reinforcing filler in particular silica or carbon black or a mixture of silica and carbon black
  • the total content of reinforcing filler is preferably within a range from 50 to 120 phr, more preferably within a range from 70 to 100 phr.
  • the reinforcing filler comprises predominantly an inorganic filler, in particular silica; in such a case, the inorganic filler, in particular silica, is present at a content preferably of between 70 and 120 phr, in combination or not with carbon black in a minor amount; the carbon black, when it is present, is preferably used at a content of less than 15 phr, more preferably less than 10 phr (for example between 0.1 and 10 phr).
  • - x is an integer from 2 to 8 (preferably from 2 to 5);
  • A is a divalent hydrocarbon radical (preferably, C ⁇ -C ⁇ s alkylene groups or C 6 -
  • Ci 2 arylene groups more particularly Ci-C 10 , in particular C C 4 , alkylenes, especially propylene);
  • the R1 radicals which are unsubstituted or substituted and identical to or different from one another, represent a Ci-C 18 alkyl, C 5 -Ci 8 cycloalkyl or C 6 - C 18 aryl group (preferably, Cj-Q alkyl, cyclohexyl or phenyl groups, in particular d-C 4 alkyl groups, more particularly methyl and/or ethyl),
  • the R.2 radicals which are unsubstituted or substituted and identical to or different from one another, represent a Cj-Cig alkoxyl or C 5 -C 18 cycloalkoxyl group (preferably a group chosen from Ci-C 8 alkoxyls and C 5 -C 8 cycloalkoxyls, more preferably still a group chosen from C[-C 4 alkoxyls, in particular methoxyl and ethoxyl),
  • the mean value of the "x" index is a fractional number preferably of between 2 and 5, more preferably in the vicinity of 4.
  • silane polysulphides of bis((C ] -C 4 )alkoxyl(C ⁇ -C 4 )alkylsilyl(C i -C 4 )alkyl)polysulphides (in particular disulphides, trisulphides or tetrasulphides), such as, for example, bis(3- trimethoxysilylpropyl) or bis(3-triethoxysilylpropyl)polysulphides.
  • TESPT bis(3-triethoxysilylpropyl)tetrasulphide
  • TESPD bis(3- triethoxysilylpropyl)disulphide
  • TESPD bis(C2HsO) 3 Si(CH 2 )3S] 2 .
  • silanes bearing at least one thiol (-SH) function referred to as mercaptosilanes
  • at least one blocked thiol function such as described, for example, in patents or patent applications US 6 849 754, WO 99/09036, WO 2006/023815 or WO 2007/098080.
  • the content of coupling agent is preferably between 2 and 15 phr, more preferably between 3 and 12 phr.
  • a reinforcing filler of another nature might be used as filler equivalent to the reinforcing inorganic filler described in the present section, provided that this reinforcing filler is covered with an inorganic layer, such as silica, or else comprises, at its surface, functional sites, in particular hydroxyls, requiring the use of a coupling agent in order to form the connection between the filler and the elastomer.
  • an inorganic layer such as silica
  • the rubber composition of the tread of the tire according to the present invention comprises cork particles within a range of more than 15 phr and less than 100 phr, said particles having a median size by weight of more than 0.5 mm and less than 3 mm in the vulcanized (or cured) state.
  • this content is preferably within a range from 20 to 80 phr, more preferably within a range from 20 to 60 phr, still more preferably within a range from 20 to 50 phr.
  • the median size by weight of the particles of cork in the vulcanized state is more than 0.5 mm and less than 3 mm. Below the indicated minimum, the targeted technical effect is insufficient, where above the recommended maximum, there is a risk too of worsening wear resistance of the tire. For this reason, the median size by weight in the vulcanized state is preferably between 0.7 and 3 mm, more preferably between 1 and 3 mm.
  • the particles of cork are in the form of a powder, microbeads, granules, balls or mixtures thereof. More preferably, the particles are in the form of granules due in particular to an easy availability.
  • cork is natural cork.
  • various known methods can be applied, for example via laser scattering (for example according to ISO-8130-13 or JIS K5600-9-3) or image analysis from optical or electron microscopes or from photomicrographs (for example according to ISO-13322-1 or JIS Z8827-1).
  • the median diameter (or median size) by weight is ultimately calculated in a known manner starting from the distribution of the particle size by number, whatever the form of the particles, said particles being considered as spheres of equivalent volume and density. 5-5.
  • the rubber composition of the tread of the tire according to the present invention can comprise all or a portion of the usual additives generally used in the elastomer compositions intended for the manufacture of treads for tires, such as, for example, pigments, protection agents, such as antiozone waxes, chemical antiozonants, antioxidants, antifatigue agents, reinforcing resins, such as methylene acceptors (for example phenolic novolac resin) or methylene donors (for example HMT or H3M), a crosslinking system based either on sulphur or on donors of sulphur and/or peroxide and/or bismaleimides, vulcanization accelerators, or vulcanization activators.
  • pigments such as, for example, pigments, protection agents, such as antiozone waxes, chemical antiozonants, antioxidants, antifatigue agents, reinforcing resins, such as methylene acceptors (for example phenolic novolac resin) or methylene donors (for example HMT or H3M),
  • the rubber composition can also comprise coupling activators when a coupling agent is used, agents for covering the inorganic filler or more generally processing aids capable, in a known way, by virtue of an improvement in the dispersion of the filler in the rubber matrix and of a lowering of the viscosity of the compositions, of improving their property of processing in the raw state; these agents are, for example, hydrolysable silanes, such as alkylalkoxysilanes, polyols, polyethers, amines, or hydroxylated or hydrolysable polyorganosiloxanes. 5-6. Manufacture of the rubber compositions and of the treads
  • the rubber compositions composing the tread of the present invention is manufactured in appropriate mixers using two successive preparation phases according to a general procedure well known to a person skilled in the art: a first phase of thermomechanical working or kneading (sometimes described as “nonproductive” phase) at high temperature, up to a maximum temperature of between 130°C and 200°C, preferably between 145°C and 185°C, followed by a second phase of mechanical working (sometimes described as "productive” phase) at a lower temperature, typically of less than 120°C, for example between 60°C and 100°C, finishing phase during which the crosslinking or vulcanization system is incorporated.
  • a first phase of thermomechanical working or kneading sometimes described as "nonproductive” phase
  • a second phase of mechanical working sometimes described as "productive” phase
  • a process which can be used for the manufacture of such compositions forming the tread of the tire according to the present invention comprises, for example and preferably, the following steps:
  • the first (non-productive) phase is carried out in a single thermomechanical stage during which all the necessary constituents, the optional additional covering agents or processing aids, and various other additives, with the exception of the crosslinking system, are introduced into an appropriate mixer, such as a normal internal mixer.
  • an appropriate mixer such as a normal internal mixer.
  • the crosslinking system is then incorporated at low temperature, generally in an external mixer, such as an open mill; everything is then mixed (productive phase) for a few minutes, for example between 5 and 15 min.
  • the crosslinking system proper is preferably based on sulphur and on a primary vulcanization accelerator, in particular on an accelerator of sulphenamide type.
  • a primary vulcanization accelerator in particular on an accelerator of sulphenamide type.
  • various known secondary accelerators or vulcanization activators such as zinc oxide, stearic acid, guanidine derivatives (in particular diphenylguanidine), and the like, incorporated during the first nonproductive phase and/or during the productive phase.
  • the content of sulphur is preferably between 0.5 and 5.0 phr, and that of the primary accelerator is preferably between 0.5 and 8.0 phr.
  • accelerator primary or secondary of any compound capable of acting as accelerator of the vulcanization of diene elastomers in the presence of sulphur, in particular accelerators of the thiazoles type and their derivatives, accelerators of thiurams types, or zinc dithiocarbamates.
  • accelerators are more preferably chosen from the group consisting of 2-mercaptobenzothiazyl disulphide (abbreviated to "MBTS”), N-cyclohexyl-2-benzothiazole-sulphenamide (abbreviated to “CBS”), N,N-dicyclohexyl-2-benzothiazolesulphenamide (“DCBS”), N-tert-butyl- 2-benzothiazolesulphenamide (“TBBS”), N-tert-butyl-2- benzothiazolesulphenimide (“TBSI”), zinc dibenzyldithiocarbamate (“ZBEC”), tetrabenzylthiuram disulfide (“TBZTD”) and the mixtures thereof.
  • MBTS 2-mercaptobenzothiazyl disulphide
  • CBS N-cyclohexyl-2-benzothiazole-sulphenamide
  • DCBS N,N-dicyclohexyl-2-benzothiazolesulphenamide
  • the final composition thus obtained is subsequently calendered, for example in the form of a sheet or of a plaque, in particular for laboratory characterization, or else extruded in the form of a rubber profiled element which can be used directly as a part of a tire tread.
  • the density (or specific gravity) of the rubber composition of the tread of the tire is from 0.55 to 0.96 g/cm 3 in the vulcanized state. Above the indicated maximum, the targeted technical effect (noise reduction) is insufficient, where below the recommended minimum, there is a risk of worsening wear of the tire. For this reason, this content is preferably within a range from 0.60 to 0.94 g/cm 3 and more preferably within a range from 0.66 to 0.92 g cm .
  • hydrostatic method see, for example ISO-2781, ASTM D297 and ASTM D792.
  • the vulcanization (or curing) is carried out a specific way at a vulcanization (or curing) pressure of less than 1.6 MPa (notably between 0.2 and 1.6 MPa) for a sufficient time which can vary, for example, between 5 and 90 min depending in particular on the vulcanization pressure, the vulcanization system adopted and the vulcanization kinetics of the composition under consideration, which may prevent from excessively decreasing the median size by weight of the particles of cork and increasing the density of rubber composition of the tread of the tire.
  • a vulcanization (or curing) pressure of less than 1.6 MPa (notably between 0.2 and 1.6 MPa) for a sufficient time which can vary, for example, between 5 and 90 min depending in particular on the vulcanization pressure, the vulcanization system adopted and the vulcanization kinetics of the composition under consideration, which may prevent from excessively decreasing the median size by weight of the particles of cork and increasing the density of rubber composition of the tread of the tire.
  • the vulcanization pressure is preferably less than 1.4 MPa (notably between 0.2 and 1.4 MPa), more preferably at most 1.2 MPa (notably within a range from 0.4 to 1.2 MPa), still more preferably at most 1.0 MPa (notably within a range from 0.5 to 1.0 MPa).
  • the median size by weight of the particles of cork, before being incorporated in the diene elastomer, into a mixer is within a range of between 0.7 and 4.0 mm, more preferably between 0.9 and 4.0 mm, still more preferably between 1.3 and 4.0 mm.
  • the median diameter (or median size) is ultimately calculated in a known manner from the histogram of the particle size distribution.
  • Results shown in Table 2 and 3 are obtained by methods of measurements and tests mentioned in "4. MEASUREMENTS AND TESTS USED" unless otherwise instructed.
  • the rubber composition comprising the particles of cork (in these examples, natural cork) described previously can advantageously be used in the treads of tires for any type of vehicle, in particular in pneumatic tyres for passenger vehicles, as demonstrated in the following tests.
  • compositions based on diene elastomers are compared, which compositions are reinforced with a blend of silica and carbon black with which is or is not combined a fraction (50 phr) of particles of cork, 30 phr or 70 phr of a plasticizer (that is, oil and resin), according to different vulcanization pressure, 1.6 MPa (as a conventional vulcanization pressure), 1.0 MPa, 0.8 MPa or 0.5MPa, as follows: composition C-l : control composition without cork particles, with 30 phr of the plasticizer, vulcanization pressure: 1.6 MPa;
  • composition C-2 composition without cork particles, with 70 phr of the plasticizer with the goal to reduce the coast-by noise), vulcanization pressure: 1.6 MPa;
  • composition C-3 composition with 50 phr of cork particles, with 30 phr of plasticizer, vulcanization pressure: 1.6 MPa;
  • composition C-4 composition according to the present invention, with 50 phr of cork particles, with 30 phr of plasticizer, vulcanization pressure: 1.0 MPa;
  • composition C-5 composition according to the present invention, with 50 phr of cork particles, with 30 phr of the plasticizer, vulcanization pressure: 0.8 MPa
  • composition C-6 composition according to the present invention, with 50 phr of cork particles, with 30 phr of the plasticizer, vulcanization pressure: 0.5 MPa.
  • compositions were carried out in the following manner: the reinforcing fillers (carbon black, silica and its associated coupling agent), the plasticizers, the particles of cork, the diene elastomer (or blend of diene elastomers) and the various other ingredients, with the exception of the vulcanization system (sulphur and Accelerator (11)), were successively introduced into an internal mixer having an initial vessel temperature of approximately 60°C; the mixer was thus approximately 70% full (% by volume). Thermomechanical working (non-productive phase) was then carried out in one stage, which lasts in total approximately 3 to 4 minutes, until a maximum "dropping" temperature of 165°C is reached. The mixture thus obtained was recovered and cooled and then sulphur and an accelerator of sulphenamide type were incorporated on an external mixer (homofinisher) at 30°C, everything being mixed (productive phase) for an appropriate time (for example between 5 and 12 min).
  • the reinforcing fillers carbon black, silica and its associated coupling
  • compositions C-l, C-2, C-3, C-4, C-5 and C-6 thus prepared were then used as treads for radial carcass passenger vehicle pneumatic tires, denoted respectively by T-1 (the control tire), T-2, T-3 (the comparative tires) T-4, T-5 and T-6 (the tires in accordance with the present invention), with a size of 205/55 R16 conventionally manufactured and in all respects identical apart from the rubber compositions forming their treads and vulcanization pressures.
  • Table 2 indicates median sizes by weight of the particles of cork in the four compositions (C-3, C-4, C-5 and C-6) after curing of the four corresponding pneumatic tires (T-3, T-4, T-5 and T-6), and also densities and moduli (MIO) in extension, which are at the same level for the four compositions after curing of the four pneumatic tires.
  • Each of the median sizes by weight of the particles of cork was calculated starting from the distribution of sizes by number, which was measured via images from photomicroscopes (enlargement of x7) in accordance with ISO-13322-1, on each of transverse cross sections made through each of the four compositions. For this calculation, the particles of this size distribution, whatever their form, where considered as spheres of equivalent volume and density.
  • results expressed in Table 2 reveal that the median sizes by weight of the particles in the compositions (C-4, C-5 and C-6) in accordance with the present invention are larger than that in the comparative composition (C-3), and the densities of the compositions in accordance with the present invention are lower than that of the comparative composition (C-3); these results clearly show that the median size and the density strongly depend on the fabrication process (vulcanization pressure).
  • Table 2 reveals that the compositions comprising the particles of cork (C-3, C-4, C-5 and C-6) in comparison with the control (C-l) already constitutes an unexpected result for a person skilled in the art: we note indeed that moduli (M10) in extension remain constant in spite of high amount of cork, which is favourable to the mechanical behaviour of the tread and thus to the stability performance of the tire.
  • Table 2 shows also another composition (C-2) comprising higher content of the plasticizer than others has lower M10 than others, which is unfavourable to the mechanical behaviour of the tread and thus to the stability performance of the tire.
  • the tires (T-4, T-5 and T-6) of the present invention emit less noise than not only the first comparative tire (T-2) with a higher level of plasticizer and devoid of cork, but also the second comparative tire (T-3) using as tread a rubber composition having a higher density (0.98 g/cm ).
  • the tread of the tire in accordance with the present invention comprising in particular a high level of particles of cork, gives the tires a better anti-noise performance, especially regarding the coast-by noise, while maintaining or even improving the stability performance of the tire.
  • Granular natural cork from ISHII SANSYOU (median size by weight of the particles measured via sieving: 2 mm);

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  • Chemical Kinetics & Catalysis (AREA)
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  • Mechanical Engineering (AREA)
  • Materials Engineering (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
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Abstract

La présente invention concerne un pneu, un pneu à l'état non vulcanisé ou un pneu vulcanisé, ayant une bande de roulement qui comprend une composition de caoutchouc. Cette composition de caoutchouc comprend au moins : un élastomère diénique, 20 à 100 pce de plastifiant, 20 à 150 pce d'une charge de renfort, et plus de 15 pce et moins 100 pce de particules de liège. Ledit plastifiant est choisi dans le groupe constitué par les plastifiants liquides, les résines hydrocarbonées et leurs mélanges. À l'état vulcanisé, lesdites particules de liège ont une taille moyenne en poids supérieure à 0,5 mm et inférieure à 3 mm. À l'état vulcanisé, ladite composition de caoutchouc présente une masse volumique de 0,55 à 0,96 g/cm33. La présente invention rend possible une meilleure performance anti-bruit, en particulier concernant le bruit de passage, tout en conservant ou même en améliorant la performance de stabilité du pneu.
PCT/JP2015/069369 2014-06-30 2015-06-30 Pneu présentant une bande de roulement comprenant des particules de liège WO2016002967A1 (fr)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019043820A1 (fr) * 2017-08-30 2019-03-07 Compagnie Generale Des Etablissements Michelin Pneu présentant une bande de roulement comprenant une composition de caoutchouc
US10457797B2 (en) * 2017-04-04 2019-10-29 The Goodyear Tire & Rubber Company Tire with tread with oxidized carbon black
US20200385550A1 (en) * 2017-12-14 2020-12-10 Compagnie Generale Des Etablissements Michelin Aircraft tire
CN116635435A (zh) * 2020-12-22 2023-08-22 米其林集团总公司 包含废胶末的橡胶组合物

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GB368411A (en) * 1930-12-12 1932-03-10 Ewald Goltstein Improved tyre for motor cars and the like
JPH02167353A (ja) * 1988-03-10 1990-06-27 Sumitomo Rubber Ind Ltd ゴム組成物及びそれをトレッドに用いたタイヤ
JPH08269242A (ja) * 1995-03-28 1996-10-15 Toyoda Gosei Co Ltd ガスケット用ニトリルゴム配合物
JPH09278941A (ja) * 1996-04-11 1997-10-28 Sumitomo Bakelite Co Ltd タイヤ用ゴム組成物
JP2007506609A (ja) * 2003-07-15 2007-03-22 カーコースティクス テック センター ゲゼルシャフト ミット ベシュレンクテル ハフツング 音響効果がある自動車用ホイールハウスカバー

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JPS619151Y2 (fr) * 1980-08-28 1986-03-22
FR2993889B1 (fr) * 2012-07-27 2014-08-22 Michelin & Cie Composition de caoutchouc thermo-expansible pour pneumatique

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Publication number Priority date Publication date Assignee Title
GB368411A (en) * 1930-12-12 1932-03-10 Ewald Goltstein Improved tyre for motor cars and the like
JPH02167353A (ja) * 1988-03-10 1990-06-27 Sumitomo Rubber Ind Ltd ゴム組成物及びそれをトレッドに用いたタイヤ
JPH08269242A (ja) * 1995-03-28 1996-10-15 Toyoda Gosei Co Ltd ガスケット用ニトリルゴム配合物
JPH09278941A (ja) * 1996-04-11 1997-10-28 Sumitomo Bakelite Co Ltd タイヤ用ゴム組成物
JP2007506609A (ja) * 2003-07-15 2007-03-22 カーコースティクス テック センター ゲゼルシャフト ミット ベシュレンクテル ハフツング 音響効果がある自動車用ホイールハウスカバー

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10457797B2 (en) * 2017-04-04 2019-10-29 The Goodyear Tire & Rubber Company Tire with tread with oxidized carbon black
WO2019043820A1 (fr) * 2017-08-30 2019-03-07 Compagnie Generale Des Etablissements Michelin Pneu présentant une bande de roulement comprenant une composition de caoutchouc
US20200385550A1 (en) * 2017-12-14 2020-12-10 Compagnie Generale Des Etablissements Michelin Aircraft tire
CN116635435A (zh) * 2020-12-22 2023-08-22 米其林集团总公司 包含废胶末的橡胶组合物

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