WO2014112654A1 - Composition de caoutchouc - Google Patents

Composition de caoutchouc Download PDF

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Publication number
WO2014112654A1
WO2014112654A1 PCT/JP2014/051314 JP2014051314W WO2014112654A1 WO 2014112654 A1 WO2014112654 A1 WO 2014112654A1 JP 2014051314 W JP2014051314 W JP 2014051314W WO 2014112654 A1 WO2014112654 A1 WO 2014112654A1
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Prior art keywords
rubber
weight
parts
rubber composition
sbr
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PCT/JP2014/051314
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English (en)
Japanese (ja)
Inventor
山口 毅
務 高嶋
辰夫 山口
正哲 金
達也 千羽
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Jx日鉱日石エネルギー株式会社
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Publication of WO2014112654A1 publication Critical patent/WO2014112654A1/fr

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    • BPERFORMING OPERATIONS; TRANSPORTING
    • B60VEHICLES IN GENERAL
    • B60CVEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
    • B60C1/00Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L9/00Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
    • C08L9/06Copolymers with styrene

Definitions

  • the present invention relates to a rubber composition having excellent grip properties when applied to a tire, and a rubber having excellent grip properties when applied to a tire formed by crosslinking the rubber composition.
  • Crosslinked products of diene rubbers such as styrene butadiene copolymer rubber (SBR) have excellent grip characteristics and are used, for example, in the tread portion of a tire in contact with the road surface, but due to olefin bonds in the main chain. , Heat resistance, weather resistance, ozone degradation resistance, etc. may be a problem.
  • ⁇ -olefin-nonconjugated diene copolymer rubbers such as butyl rubber (IIR) containing a small amount of olefin bond in the main chain and EPDM containing olefin bond only in the side chain have good heat resistance and weather resistance. is there.
  • butyl rubber containing a small amount of olefinic bonds in the main chain and ⁇ -olefin-nonconjugated diene copolymer containing olefinic bonds only in the side chain, in order to improve the properties of the diene rubber while maintaining the grip characteristics.
  • the rubber composition of the rubber and its cross-linked rubber have been studied, and proposals have been made mainly for SBR / IIR and SBR / EPDM systems.
  • the rubber having a main chain structure typified by butyl rubber is grasped by the change in tan ⁇ .
  • the improvement effect of grip performance (also referred to as tread characteristics) of diene rubber has been recognized.
  • Patent Document 3 rubber having an olefin structure only in the side chain
  • Patent Document 4 modification of butyl rubber to diene rubber by addition of minerals mainly composed of sepiolite
  • Patent Document 5 Modification of butyl rubber with respect to diene rubber by use of phosphorous vulcanization accelerator
  • Patent Document 6 modification of modified butyl rubber with respect to diene rubber by addition of specific chemical substances
  • the present inventors selected SBR as the diene rubber and a rubber having an isobutylene main chain structure typified by butyl rubber as the modifier, and the molecular structure between them, By specifying the molecular weight relationship, it was found that a rubber having a particularly high grip performance was obtained, and the present invention was completed.
  • 100 parts by weight of a styrene-butadiene copolymer in which the rubber component is a styrene-butadiene copolymer and the cis-1,4 bond unit in the microstructure of the butadiene unit is 40% by weight or more.
  • the unit represented by the following formula (1) contains 100 to 90% by weight
  • the unit represented by the following formula (2) contains 0 to 10% by weight (both are 100% by weight).
  • the present invention relates to a rubber composition containing 0.5 to 70 parts by weight of a polymer.
  • the second of the present invention is characterized in that the isobutylene polymer has a weight average molecular weight (Mw) of 5,000 to 100,000 and a molecular weight distribution dispersity (Mw / Mn) of 3.0 or less.
  • the present invention relates to a first rubber composition of the present invention.
  • a third aspect of the present invention relates to the first or second rubber composition of the present invention, wherein the styrene-butadiene copolymer rubber has a butadiene content of 70% by weight or more.
  • a fourth aspect of the present invention relates to the rubber composition according to any one of the first to third aspects of the present invention, wherein the Mooney viscosity (ML 1 + 4 , 100 ° C.) is 30 to 50.
  • a fifth aspect of the present invention relates to a rubber obtained by crosslinking the rubber composition according to any one of the first to fourth aspects of the present invention.
  • a sixth aspect of the present invention relates to a tire characterized by comprising the fifth rubber of the present invention as a constituent material.
  • a solution-polymerized styrene-butadiene copolymer having a cis-1,4-bond unit content of the butadiene unit of the diene polymer of 40% by weight or more is used.
  • These copolymers are described as S-SBR and are commercially available.
  • “Toughden” manufactured by Asahi Kasei Chemicals Corporation can be raised.
  • the microstructure of butadiene includes a cis-1,4 bond, a trans-1,4 bond, and a 1,2-bond.
  • the cis of the butadiene unit is analyzed by the following analysis method. -1 and 4 units whose content is analyzed to be 40% by weight or more are used.
  • the content of cis-1,4 bonds in ordinary styrene butadiene is less than 35% by weight according to this analysis method.
  • the ratio of cis-1,4 bonds in the styrene-butadiene copolymer is carried out in accordance with JIS K6239 “How to Determine the Microstructure of Raw Rubber-Solution Polymerized SBR (Quantitative)”.
  • the extracted SBR sample is subjected to 1 H-NMR measurement and IR measurement to contain cis-1,4 bond unit, trans-1,4 bond unit, 1,2 unit bond and styrene of butadiene unit in SBR. The rate was calculated.
  • the compatibility with other rubber components also changes.
  • a rubber having an isobutylene main chain structure represented by butyl rubber which has excellent compatibility or so-called microphase separation in response to this change has not been known.
  • the main chain structure is represented by the following formula (1) and, if necessary, the following formula (2), and the unit of the formula (1) is 100 to 90
  • An isobutylene polymer having a weight percentage of 0 to 10 wt% of the unit of the formula (2) (both are 100 wt% in total) is used.
  • the present inventors consider that these isobutylene polymers are excellent in compatibility with S-SBR and constitute so-called microphase separation, judging from the results of Examples described later. That is, by configuring this microphase separation, the total interfacial area with the isobutylene polymer finely dispersed in S-SBR increases, and in the blend system, the formulas (1) and (2), It is considered that the viscoelastic characteristics of the structure mainly represented by the formula (1) are efficiently transmitted to the S-SBR, and the grip performance when applied to a tire is improved.
  • S-SBR as a continuous phase (or matrix) and an isobutylene-based polymer as a dispersed phase (or domain).
  • the isobutylene polymer is used in an amount of 0.5 to 70 parts by weight with respect to 100 parts by weight of S-SBR. If the amount is 0.5 parts by weight or less, the effect of modifying the isobutylene polymer cannot be sufficiently obtained. If the amount exceeds 70 parts by weight, the phase structure tends to become unstable.
  • the improvement in grip performance according to the present invention mainly depends on the structure represented by the formula (1) in the isobutylene-based polymer, and therefore the ratio of the structural unit represented by the formula (2) is isobutylene.
  • the content is preferably 10% by weight or less based on the total weight of the polymer.
  • the weight average molecular weight (Mw) of the isobutylene polymer is reduced, and the molecular weight distribution It is also preferable to reduce the dispersity (Mw / Mn). Specifically, it is preferable that the weight average molecular weight (Mw) is 5,000 to 100,000 and the dispersity (Mw / Mn) is 3.0 or less.
  • butadiene having a cis-1,4 bond structure in S-SBR which is considered highly compatible with the isobutylene polymer. It is preferable to increase the unit weight as much as possible, and the butadiene content in S-SBR is preferably 70% by weight or more.
  • the isobutylene polymers according to the present invention those having substantially only the structural unit represented by the formula (1) can be obtained from the market. An example is “Tetrax 3T (trade name)” manufactured by JX Nippon Oil & Energy Corporation.
  • the thing containing 10% or less of structural units represented by Formula (2) among the isobutylene-type polymers which concern on this invention can also be obtained from a market.
  • An example is “BUTYL 268” manufactured by JSR Corporation (the content of the structural unit of the formula (2) is 1.8% by weight).
  • a diene rubber other than S-SBR may be included as a rubber component.
  • SBR styrene-butadiene copolymer
  • NR natural rubber
  • BR butadiene rubber
  • IR isoprene rubber
  • nitrile butadiene having a butadiene unit having a cis-1,4 bond content of less than 35% by weight.
  • NBR chloroloprene rubber
  • CR chloroloprene rubber
  • EPDM 1,6-hexadiene, dicyclopentadiene, ethylidene norbornene, or the like. These may use only 1 type and can also use 2 or more types together.
  • a normal rubber A chemical used in processing is blended to perform crosslinking.
  • the isobutylene polymer in the present invention substantially contains only the formula (1) as a repeating unit, it is substantially crosslinked. Absent. Even in the final rubber, it is considered to function as an uncrosslinked dispersed phase.
  • the cross-linking of the isobutylene polymer itself and the co-crosslinking of S-SBR and the isobutylene polymer proceed, and the compatibility between the two. Will be further improved.
  • preferable ones are sulfur-based crosslinking from the viewpoint of grip characteristics when applied to a tire.
  • peroxide crosslinking is carried out when the cross-linking of the isobutylene polymer itself and the co-crosslinking of both including S-SBR are advanced. Is preferred.
  • formula (1) causes molecular chain scission
  • a highly reactive crosslinking agent such as divinylbenzene or m-phenylenebismaleimide.
  • the Mooney viscosity of the rubber composition before crosslinking is not limited, but the Mooney viscosity (ML 1 + 4 , 100 ° C.) is preferably 30-50. Outside these ranges, the torque in kneading becomes excessive and insufficient, and the dispersion structure is not sufficiently secured and the dispersion / diffusion of various additives, etc., is insufficient, and the effects of the present invention may not be sufficiently obtained.
  • the reinforcing agent include carbon black and silica.
  • Carbon black is suitably used as a reinforcing agent from the viewpoints of improving wear resistance, improving rolling resistance characteristics, preventing cracks and cracks caused by ultraviolet rays (preventing ultraviolet degradation), and the like.
  • the type of carbon black is not particularly limited, and conventionally known carbon blacks such as furnace black, acetylene black, thermal black, channel black, and graphite can be used.
  • the physical characteristics such as particle size, pore volume and specific surface area of carbon black are not particularly limited, and various carbon blacks conventionally used in the rubber industry, for example, SAF, ISAF, HAF, FEF, GPF, SRF (all are abbreviations of carbon black classified according to the US ASTM standard D-1765-82a) and the like can be used as appropriate.
  • the blending amount is preferably 5 to 80 parts by mass, and more preferably 10 to 60 parts by mass with respect to 100 parts by mass of the rubber component (A). Further, it can be 30 to 80 parts by mass, or 40 to 60 parts by mass. In such a blending amount, the effect as a reinforcing agent can be favorably obtained in the rubber composition and the crosslinked rubber composition according to the present embodiment.
  • silica those conventionally used as rubber reinforcing agents can be used without particular limitation, for example, dry method white carbon, wet method white carbon, synthetic silicate white carbon, colloidal silica, precipitated silica and the like. Can be mentioned.
  • the specific surface area of silica is not particularly limited, but usually a silica having a surface area of 40 to 600 m 2 / g, preferably 70 to 300 m 2 / g, and a primary particle diameter of 10 to 1000 nm should be used. Can do. These may be used alone or in combination of two or more.
  • the amount of silica used is preferably 0.1 to 150 parts by weight, more preferably 10 to 100 parts by weight, and 30 to 100 parts by weight with respect to 100 parts by weight of the rubber component (A). Is more preferable. Moreover, you may mix
  • silane coupling agent examples include vinyltrichlorosilane, vinyltriethoxysilane, vinyltris ( ⁇ -methoxy-ethoxy) silane, ⁇ - (3,4-epoxycyclohexyl) -ethyltrimethoxysilane, and 3-chloropropyltrimethoxy.
  • the addition amount of the silane coupling agent can be appropriately changed depending on the desired blending amount of silica, but is preferably 0.1 to 20 parts by mass with respect to 100 parts by mass of the rubber component (A).
  • the filler mineral powders such as clay and talc, carbonates such as magnesium carbonate and calcium carbonate, alumina hydrate such as aluminum hydroxide, and the like can be used.
  • plant oil softeners such as tall oil, mainly linoleic acid, oleic acid, and abithienic acid, pineapple, rapeseed oil, cottonseed oil, peanut oil, castor oil, palm oil, fuacitis, paraffinic oil, Examples thereof include naphthenic oils, aromatic oils, and phthalic acid derivatives such as dibutyl phthalate.
  • the blending amount of the softening agent is preferably 0 to 50 parts by mass with respect to 100 parts by mass of the rubber component (A).
  • the rubber composition according to this embodiment also includes various additives used in the field of the rubber industry, such as anti-aging agents, sulfur, crosslinking agents, vulcanization accelerators, vulcanization retarders, peptizers, processes. You may contain 1 type, or 2 or more types, such as oil and a plasticizer, as needed.
  • the compounding amount of these additives is preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the rubber component (A).
  • Antiaging agents include primary amines such as p, p′-diaminodiphenylmethane; secondary amines such as phenyl- ⁇ -naphthylamine and N, N′-diphenyl-p-phenylenediamine; 2,6-di Examples include alkylphenols such as tert-butyl-p-cresol, 2,5-ditert-butyl-hydroquinone and hydroquinone monobenzyl ether; and imidazoles such as 2-mercaptobenzimidazole.
  • the blending amount is preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the rubber component (A).
  • vulcanization accelerator examples include thiuram accelerators such as tetramethylthiuram monosulfide, tetramethylthiuram disulfide, and tetraethylthiuram disulfide; thiazole accelerators such as 2-mercaptobenzothiazole and dibenzothiazyl disulfide; N-cyclohexyl Sulfenamide accelerators such as 2-benzothiazylsulfenamide and N-oxydiethylene-2-benzothiazolylsulfenamide; guanidine accelerators such as diphenylguanidine and diortolylguanidine; n-butyraldehyde -Aldehyde-amine accelerators such as aniline condensates and butyraldehyde-monobutylamine condensates; aldehyde-ammonia accelerators such as hexamethylenetetramine; thiourea accelerators such as thiocarbanilide
  • Vulcanization aids include metal oxides such as zinc oxide (zinc white) and magnesium oxide; metal hydroxides such as calcium hydroxide; metal carbonates such as zinc carbonate and basic zinc carbonate; stearic acid and oleic acid Aliphatic acid salts such as zinc stearate and magnesium stearate; amines such as di-n-butylamine and dicyclohexylamine; ethylene dimethacrylate, diallyl phthalate, N, Nm-phenylenebismaleimide, triallyl isocyanurate And trimethylolpropane trimethacrylate.
  • metal oxides such as zinc oxide (zinc white) and magnesium oxide
  • metal hydroxides such as calcium hydroxide
  • metal carbonates such as zinc carbonate and basic zinc carbonate
  • stearic acid and oleic acid Aliphatic acid salts such as zinc stearate and magnesium stearate
  • amines such as di-n-butylamine and dicyclohexylamine
  • the content of the vulcanization aid is preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the rubber component (A).
  • the rubber composition according to the present embodiment can be produced by applying a method generally used as a method for producing a rubber composition. For example, it can manufacture by mixing each component mentioned above using kneading machines, such as a Brabender, a Banbury mixer, and a roll mixer.
  • Example 1 As styrene-butadiene copolymer rubber (hereinafter abbreviated as SBR), solution-polymerized styrene-butadiene rubber, trade name “Tuffden 1000” (manufactured by Asahi Kasei Chemicals Co., Ltd.), and polyisobutylene polymer as polyisobutylene, trade name “Tetrax 3T” (manufactured by JX Nippon Oil & Energy Corporation, Mw 32,000, Mw / Mn 2.0) was used.
  • SBR styrene-butadiene copolymer rubber
  • Tuffden 1000 solution-polymerized styrene-butadiene rubber
  • polyisobutylene polymer trade name “Tetrax 3T” (manufactured by JX Nippon Oil & Energy Corporation, Mw 32,000, Mw / Mn 2.0) was used.
  • a filler, a plasticizer, a vulcanizing agent, a vulcanization accelerator, a vulcanization aid, and an anti-aging agent are blended in the amounts shown in Table 1 in 100 parts by weight of the above SBR and 10 parts by weight of polyisobutylene, respectively. 6 inch ⁇ ⁇ 16 inch) and kneading under the conditions of a rotation speed of 30 rpm and a front-rear roll rotation ratio of 1: 1.22 to obtain a rubber composition having a predetermined Mooney viscosity.
  • Silica AQ (manufactured by Tosoh Silica) is used as the filler, process oil “NS-100” (manufactured by Idemitsu Kosan Co., Ltd.) as the plasticizer, and sulfur (Kawagoe Chemical Co., Ltd.) as the vulcanizing agent.
  • Zinc Oxide No. 3 (Hakusui Tech Co., Ltd.) and stearic acid (made by Nippon Seika Co., Ltd.) as vulcanization aids
  • sulfenamide accelerators as vulcanization accelerators.
  • Example 2 Vulcanization characteristics and dynamic viscoelasticity (that is, an index of grip resistance) at the time of producing the sheet were evaluated. These results are shown in Table 3.
  • Example 2 The same procedure as in Example 1 was performed except that 100 parts by weight of solution-polymerized styrene-butadiene rubber, trade name “Tuffden 2000R” (manufactured by Asahi Kasei Chemicals Corporation) was used as SBR.
  • Example 3 As SBR, 70 parts by weight of solution-polymerized styrene-butadiene rubber, trade name “Tuffden 2000R” (manufactured by Asahi Kasei Chemicals Corporation) is used, and butadiene rubber (BR) (trade name “BR1220”, produced by Nippon Zeon Co., Ltd.). ) The same operation as in Example 1 was carried out except that 30 parts by weight was added (see Table 2). The polyisobutylene used in Example 4 below is prepared as follows.
  • the flask was immersed in a low temperature bath at a predetermined temperature, and after confirming that the liquid temperature in the system reached 10 ° C., 30 g of isobutylene was transferred to the reaction system.
  • EADC 0.1 mol / L ethylaluminum dichloride
  • Example 4 As SBR, 100 parts by weight of solution-polymerized styrene-butadiene rubber, trade name “Tuffden 2000R” (manufactured by Asahi Kasei Chemicals Co., Ltd.) was used, and Mw11,000 and Mw / Mn2.6 polyisobutylene (in the above synthesis method) Preparation) was carried out in the same manner as in Example 1, except that 10 parts by weight were used.
  • Example 5 As SBR, 100 parts by weight of solution-polymerized styrene-butadiene rubber, trade name “Toughden 2000R” (manufactured by Asahi Kasei Chemicals Corporation), and polyisobutylene (synthetic product) of Mw 97,000 and Mw / Mn 1.9 as additives are used. It implemented like Example 1 except having used 10 weight part.
  • Example 6 As SBR, 70 parts by weight of solution-polymerized styrene-butadiene rubber, trade name “Tuffden 2000R” (manufactured by Asahi Kasei Chemicals Corporation) and butyl rubber as an additive, trade name “BUTYL 268” (manufactured by JSR Corporation): ( Example 2 was carried out in the same manner as in Example 1 except that 30 parts by weight of the content of 1.8% by weight was used. [Comparative Example 1] The same procedure as in Example 1 was performed except that solution-polymerized styrene-butadiene rubber, “SL-552 (manufactured by JSR Corporation)” was used as SBR.
  • SL-552 solution-polymerized styrene-butadiene rubber
  • Example 2 The same procedure as in Example 1 was performed except that solution-polymerized styrene-butadiene rubber, “SL-563 (manufactured by JSR Corporation)” was used as SBR.
  • SBR solution-polymerized styrene-butadiene rubber
  • SBR solution-polymerized styrene-butadiene rubber
  • Example 4 The SBR was carried out in the same manner as in Example 1 except that “Tuffden 2003 (manufactured by Asahi Kasei Chemicals Corporation)” was used as the solution-polymerized styrene-butadiene rubber.
  • Comparative Example 5 As SBR, solution polymerized styrene-butadiene rubber, trade name “Toughden 2000R” (manufactured by Asahi Kasei Chemicals Corporation) was used, and polyisobutylene (synthetic product) of Mw 3,800 and Mw / Mn 2.9 was used as an additive. Except for this, the same procedure as in Example 1 was performed.
  • one test piece having a thickness of 1 mm, a width of 5 mm, and a length of 40 mm was cut out from the sheets obtained in Examples 1 and 2 and Comparative Examples 1 to 5, and the frequency was 10 Hz and the dynamic strain was 0.
  • the measurement temperature was measured in the tensile mode while the temperature was raised in the range of ⁇ 50 to 100 ° C. at 2 ° C./min.
  • the apparatus used is a dynamic viscoelasticity measuring apparatus RSA-3 (manufactured by TA INSTRUMENTS).
  • the wet grip property correlates with a loss coefficient (tan ⁇ ) value at 10 Hz-0 ° C., and the wet grip property (brake braking property) is better as the value is larger. It is known. Table 3 shows the measurement results. Examples 1 to 6 have a large 0 ° C. tan ⁇ value (good grip properties). In addition, the vulcanization speed is fast and the productivity is excellent.
  • the rubber composition of the present invention can be particularly suitably used for tire applications.
  • automobile tires and tubes, inner liners, bead fillers, plies, belts, tread rubbers, side rubbers, various sealing materials, sealants, and aircraft use It can be used for applications such as tires and tubes, bicycle tires and tubes, solid tires, and corrected tires. In addition to tire applications, it can be used for applications such as shoe soles, grips for golf and tennis clubs, golf balls, tennis balls, and the like.
  • the rubber composition according to the present invention can achieve both improvement in productivity due to an increase in the crosslinking speed and improvement in gripping properties, and can be particularly suitably used for tire tread applications. There is a possibility that it can be used for applications such as grips for clubs such as tennis, golf balls, tennis balls and the like.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Tires In General (AREA)

Abstract

Cette invention concerne une composition de caoutchouc ayant une excellente résistance à l'adhérence, qui contient un copolymère de styrène-butadiène à titre de composant de caoutchouc, ladite composition de caoutchouc comprenant : 100 parties en poids d'un copolymère de styrène-butadiène ayant une teneur en liaison cis-1,4 dans la microstructure d'un motif butadiène de 40 % en poids ou plus ; et 0,5 à 70 parties en poids d'un polymère d'isobutyrène qui comprend 100 à 90 % en poids d'un motif structural représenté par la formule (1) et 0 à 10 % en poids d'un motif de liaison à l'isoprène représenté par la formule (2).
PCT/JP2014/051314 2013-01-17 2014-01-16 Composition de caoutchouc WO2014112654A1 (fr)

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JP2013006463A JP2014136759A (ja) 2013-01-17 2013-01-17 ゴム組成物

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Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3199189A4 (fr) * 2014-10-02 2018-07-11 Sumitomo Rubber Industries, Ltd. Capuchon de buse
WO2020075829A1 (fr) * 2018-10-10 2020-04-16 株式会社ブリヂストン Composition de caoutchouc, bande de roulement, et pneumatique
JP7275460B2 (ja) * 2018-12-11 2023-05-18 株式会社ブリヂストン タイヤトレッド用ゴム組成物及びタイヤ

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11315171A (ja) * 1998-03-04 1999-11-16 Bridgestone Corp ゴム組成物及びそれを用いた空気入りタイヤ
JP2000351873A (ja) * 1999-06-11 2000-12-19 Yokohama Rubber Co Ltd:The ゴム組成物
JP2003301075A (ja) * 2002-04-11 2003-10-21 Toyo Tire & Rubber Co Ltd 低温用スチレンブタジエンゴム組成物及びその成形体
JP2012172022A (ja) * 2011-02-18 2012-09-10 Jx Nippon Oil & Energy Corp ゴム組成物、架橋ゴム組成物及び空気入りタイヤ

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11315171A (ja) * 1998-03-04 1999-11-16 Bridgestone Corp ゴム組成物及びそれを用いた空気入りタイヤ
JP2000351873A (ja) * 1999-06-11 2000-12-19 Yokohama Rubber Co Ltd:The ゴム組成物
JP2003301075A (ja) * 2002-04-11 2003-10-21 Toyo Tire & Rubber Co Ltd 低温用スチレンブタジエンゴム組成物及びその成形体
JP2012172022A (ja) * 2011-02-18 2012-09-10 Jx Nippon Oil & Energy Corp ゴム組成物、架橋ゴム組成物及び空気入りタイヤ

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