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WO1998018860A1 - Latex de caoutchouc dienique conjugue, composition de latex de caoutchouc, et caoutchouc cellulaire - Google Patents

Latex de caoutchouc dienique conjugue, composition de latex de caoutchouc, et caoutchouc cellulaire Download PDF

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Publication number
WO1998018860A1
WO1998018860A1 PCT/JP1997/003864 JP9703864W WO9818860A1 WO 1998018860 A1 WO1998018860 A1 WO 1998018860A1 JP 9703864 W JP9703864 W JP 9703864W WO 9818860 A1 WO9818860 A1 WO 9818860A1
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WO
WIPO (PCT)
Prior art keywords
carbon atoms
group
latex
polymer rubber
rubber
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP1997/003864
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English (en)
Japanese (ja)
Inventor
Katsuo Hagiwara
Katumi Sunayama
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.)
Zeon Corp
Original Assignee
Nippon Zeon Co Ltd
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 Nippon Zeon Co Ltd filed Critical Nippon Zeon Co Ltd
Priority to JP1998520275A priority Critical patent/JP4049819B6/ja
Publication of WO1998018860A1 publication Critical patent/WO1998018860A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
    • C08C19/00—Chemical modification of rubber
    • C08C19/20—Incorporating sulfur atoms into the molecule

Definitions

  • the present invention relates to a latex of a conjugated polymer rubber, a rubber latex composition containing the latex, and a rubber foam produced from the rubber latex composition.
  • the latex of a conjugated polymer rubber of the present invention is a latex of a conjugated polymer rubber in which mercaptocarboxylic acid, mercaptosulfonic acid or a derivative thereof is bonded via a thiol group thereof.
  • the latex is useful as a raw material for producing a foam having a balance between elasticity and strength.
  • foams using rubber latex have been used in various fields.
  • foams made from natural rubber, acrylonitrile Z-butadiene copolymer rubber (NBR) and styrene / butadiene copolymer rubber (SBR) latex are used as materials for cosmetic puffs and sponge rolls. Have been.
  • Polyurethane foam is a strong foam but has a poorer feel than foams derived from NBR latex and SBR latex.
  • a combination of NBR and polyurethane has been proposed.However, when NBR latex and polyurethane emulsion are used together, there is no common vulcanizing agent and polyisocyanate, a crosslinking agent for polyurethane, is used. There is a problem that the compound does not function as a crosslinking agent in the presence of a large amount of water.
  • the use of an acid-modified rubber latex copolymerized with a monomer having a propyloxyl group provides a foam with improved strength, but the texture is too hard and cannot be used for puff production. Disclosure of the invention
  • an object of the present invention is to provide a rubber latex useful as a raw material for producing a foam having a high balance between strength and elasticity.
  • Still another object of the present invention is to provide a rubber latex composition for producing a foam containing the useful rubber latex.
  • Still another object of the present invention is to provide a rubber foam having a high balance between strength and elasticity.
  • a latex of a conjugated diene polymer rubber wherein the latex is represented by the following formula (1):
  • M represents -C- ⁇ - or -S-0-
  • Ri is an aliphatic hydrocarbon group having 1 to 10 carbon atoms which may have a substituent (the aliphatic hydrocarbon group has a carboxyl group as a substituent when M is -CO-0-); Or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent.
  • n is, M is - CO- 0- 1 to 6 integer when, M is - S0 3 - 1 to represent each time,
  • the number of carbon atoms Represents an alkyl group having 1 to 15 or an alkoxyalkyl group having 2 to 8 carbon atoms,
  • R 2 may be an alkaline earth metal.
  • the at least one thiol compound represented by the formula is bonded to the polymer rubber molecule through the thiol group.
  • a rubber latex composition for producing a foam comprising a latex, a vulcanization system and, if necessary, a gelling agent of the conjugated gen-based polymer rubber.
  • the conjugated gen-based polymer rubber latex used in the present invention is characterized in that at least one thiol compound represented by the above formula (1) is converted via its thiol group (more specifically, derived from the thiol group). Conjugated diene-based polymer is bonded to a carbon atom of a rubber molecule.
  • the conjugated gen-based polymer rubber is a polymer rubber containing a conjugated gen monomer unit as an essential component, but is generally 40 to 90% by weight based on the weight of the polymer rubber. At least one unit selected from the group consisting of an ethylenically unsaturated nitrile monomer unit and an aromatic vinyl compound monomer unit; 10 to 60% by weight; and optionally, an unsaturated carboxylic acid unit of 0 to 10% by weight. And, if desired, a copolymer comprising 0 to 15% by weight of other ethylenically unsaturated monomer units.
  • conjugated gen examples include 1,3-butadiene, 2,3-dimethylbutadiene, isoprene, chloroprene, and 1,3-pentene.
  • Conjugated gens can be used alone or in combination of two or more, and the amount used for copolymerization is usually in the range of 40 to 90% by weight based on the total amount of monomers.
  • ethylenically unsaturated nitriles copolymerized with conjugated gens include: Examples include rilonitrile, methacrylonitrile, and black acrylonitrile. These ethylenically unsaturated nitriles are used alone or in combination of two or more, and the amount is usually selected in the range of 10 to 60% by weight based on the total amount of the monomers.
  • specific examples of the aromatic vinyl compound include styrene, ⁇ -methylstyrene, vinylpyridine, vinyltoluene and the like. These aromatic vinyl compounds are used alone or in combination of two or more, and their amounts are usually selected in the range of 15 to 35% by weight based on the total amount of monomers. The type and amount of the ethylenically unsaturated nitrile and the aromatic vinyl compound are appropriately selected according to the required performance of the rubber foam.
  • unsaturated carboxylic acid optionally copolymerized with a conjugated diene include (meth) acrylic acid, maleic acid, itaconic acid and fumaric acid.
  • ethylenically unsaturated monomers optionally copolymerized with a conjugated diene include monoethylenically unsaturated monomers and polyfunctional ethylenically unsaturated monomers.
  • Specific examples of the monoethylenically unsaturated monomer include those having 1 to 1 carbon atoms such as methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, and 2-ethylhexyl (meth) acrylate.
  • polyfunctional ethylenically unsaturated monomers include non-conjugated diene such as divinylbenzene; vinyl norbornene and dicyclopentene; polyethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, and the like.
  • the above unsaturated carboxylic acids and ethylenically unsaturated monomers can be used alone or in combination of two or more, and their amounts are appropriately selected within a range that does not impair the effects of the present invention.
  • the amount of unsaturated carboxylic acid is 10% by weight or less based on the total amount of monomers, and the amount of other ethylenically unsaturated monomers is 15% by weight or less based on the total amount of monomers. It is.
  • the conjugated polymer rubber is prepared by copolymerizing the above monomer components by, for example, known emulsion polymerization.
  • a reaction in which a compound having a thiol group is added to a carbon atom of a double bond in a conjugated gen-based polymer via a thioether bond (-S-) derived from the thiol group is represented by the following reaction formula. This reaction is known.
  • the latex of the conjugated gen-based polymer rubber to which the thiol compound represented by the formula (1) used in the present invention is bonded is obtained by this reaction.
  • the thiol compound represented by the above formula (1) includes a mercaptocarboxylic acid represented by the formula HS-R1COOR 2 and a derivative thereof;
  • HS-RiC OO a mercaptocarboxylic acid derivative having two or more thiol groups represented by nR 2 [2 ⁇ n ⁇ 6]; and a mercaptosulfonic acid represented by the formula HS-RiSOsR 2 and its derivatives Is included.
  • Ri has 1 to 10 carbon atoms which may have a substituent, Or a linear or branched aliphatic hydrocarbon group having 1 to 5 carbon atoms, more preferably 1 to 3 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent.
  • These aliphatic hydrocarbon groups and aromatic hydrocarbon groups may have a functional group such as a —C 00 H group or a —SH group.
  • two or more Ris are included, they may be the same or different.
  • R2 is hydrogen; sodium, Al force Li metal such as potassium ⁇ beam; expression such Anmoniumu group, hydroxy E chill ⁇ amino group - represented by NR 4 An alkyl group having 1 to 15 carbon atoms such as a methyl group, an ethyl group or an octyl group; an alkoxyalkyl group having 2 to 8 carbon atoms such as a methoxymethyl group, an ethoxyxyl group and a 3-methoxybutyl group .
  • R2 represents an organic group having 2 to 18 carbon atoms or a heterocyclic group having 2 to 5 carbon atoms, having 2 to 6 bonds corresponding to n.
  • the tool body Examples of such organic group, ethylene group, tetramethylene group, and - CH2CH2CH (CH 2 -) CH 2 CH 2 -> -CH 2 C (CH 2 -) (CH 2 -) CH 2 - , etc. And a hydrocarbon group having a structure in which a hydroxyl group is removed from the polyhydric alcohol.
  • Specific examples of the heterocyclic group having 2 to 5 carbon atoms include a tris (2-hydroxyethyl) isocyanurate residue.
  • R 2 may be an alkaline earth metal such as calcium.
  • mercaptocarboxylic acid represented by the formula HS-R1COOR 2 and derivatives thereof include thioglycolic acid, 3-mercaptopropionic acid, thiomalic acid, thiolactic acid (2-mercaptopropionic acid), methyl thioglycolate, and thioglycol.
  • mercaptocarboxylic acid derivative having two or more mercapto groups represented by the formula (HS- RiCOO) nR 2 [2 ⁇ n ⁇ 6] include 1,4-butanediol. —Rubisthiodalicholate, ethylene glycol bisthioglycolate, trimethylolpropane tristhioglycolate, pentaerythritol tetrakisthioglycolate, 1,4-butanediol bis-3-mercaptopropionate, ethylene glycol bis- 3-mercaptopropionate, trimethylolpropane tris-3-mercaptopropionate, penyu erythritol tetrakis-3-mercaptopropionate, and trihydroxyethylisosyanurate tris-3-mercaptopropionate And the like.
  • Formula HS - as completely as examples of R i S Os mercapto sulfonic acid and its derivatives represented by R 2, mercapto ethanesulfonic acid, mercapto sulfonic acid, sodium mercapto ethanesulfonic acid, and the like mercapto-propane sulfonic acid .
  • At least one thiol compound represented by the above formula (1) is bonded to a carbon atom in the molecule via the thiol group (hereinafter referred to as “thiol-modified polymer rubber”).
  • thiol-modified polymer rubber The addition of a thiol compound represented by the formula (1) to a conjugated diene polymer rubber in the form of a latex in the presence or absence of a catalyst at a temperature of room temperature to 120 ° C. Can be easily obtained by As the catalyst, persulfates, azo compounds such as azobisisobutyronitrile, and organic peroxides such as benzoyl peroxide are used.
  • the thiol-modified polymer rubber latex of the present invention can be obtained directly as a reaction product of this addition reaction.
  • mercaptocarboxylic acid When a conjugated gen-based polymer rubber is produced by emulsion polymerization, mercaptocarboxylic acid, mercaptosulfonic acid, or the like may be present in the polymerization system to cause an addition reaction simultaneously with the polymerization. In either case, a surfactant can be added to maintain the stability of the latex.
  • a solution of a conjugated gen-based polymer rubber is prepared, a thiol compound represented by the formula (1) is added, an addition reaction is performed, and a solution of the obtained reaction product is converted to latex by phase inversion. Thereby, the latex of the thiol-modified polymer rubber of the present invention can be obtained.
  • the addition rate of the thiol compound of the kind is determined by the following method.
  • the number of moles added to 0 is preferably 0.1 to 15 moles.
  • a more preferred addition rate is 1 to 10 mol.
  • the rubber latex composition for producing a foam of the present invention is obtained by mixing a latex of the thiol-modified polymer rubber with a vulcanizing system and, if necessary, a gelling agent.
  • a vulcanization system any vulcanization system used in the production of ordinary foams using rubber latex as a raw material can be used, and is not particularly limited.
  • a specific example of the vulcanization system a combination of sulfur as a vulcanizing agent, particularly colloidal sulfur, zinc white as a vulcanizing aid, and various vulcanization accelerators is most preferable.
  • the vulcanization accelerator examples include thiazole accelerators such as 2-mercaptobenzothiazole and a zinc salt thereof, dibenzothiazyldisulfide, and dithiamine-based lubamate accelerator such as getyldithine zinc rubamate. And the like.
  • the amount of the vulcanization system used is not particularly limited, but usually 0.1 to 10 parts by weight of sulfur, and 100 parts by weight of zinc rubber with respect to 100 parts by weight of the polymer rubber (solid content) in the latex. 0.5 to 10 parts by weight, the vulcanization accelerator varies depending on the type, but is about 0.1 to 5 parts by weight. These amounts are appropriately determined to satisfy the required performance of the foam.
  • Air is usually used to foam the rubber latex.
  • a gelling agent is used to fix the foaming state.
  • a silicon fluoride compound such as sodium hexafluorosilicate or hexafluorosilicate silica
  • a thermosensitive gelling agent such as polyorganosiloxane
  • the amount of the gelling agent used is not particularly limited, but is usually about 0.5 to 10 parts by weight based on 100 parts by weight of the polymer rubber (solid content) in the latex. It is also possible to use a so-called freeze-coagulation method (Tararay method) without using a gelling agent.
  • Various assistants can be added to the rubber latex, if desired.
  • Antioxidants, coloring agents, foam stabilizers, and various compounding agents are stable in rubber latex as auxiliaries.
  • Dispersing agents eg, NASF [sodium salt of naphthalenesulfonic acid formalin condensate]
  • thickeners eg, polyacrylic acid and its sodium salt, sodium alginate, polyvinyl alcohol, etc.
  • Surfactants as foaming agents eg, fatty acid alkali soaps such as potassium oleate, higher alcohol sulfates such as sodium dodecyl sulfate
  • the above-mentioned compounding agent is compounded as a dispersion depending on the kind with the latex of the thiol-modified polymer rubber of the present invention, and is uniformly mixed.
  • a conventionally known foaming method may be used.
  • the method is not particularly limited.
  • the solid content concentration of the rubber latex composition for producing a foam is adjusted to about 45 to 65% by weight, and it varies depending on the use of the foam.
  • the expansion ratio is 2 to 10%. Stir using a whisk while introducing air so that the volume becomes about twice.
  • the composition having reached a predetermined expansion ratio is poured into a foaming mold, and vulcanization is performed in a heating chamber according to a predetermined temperature and time.
  • the rubber foam thus obtained is sliced and cut into a predetermined thickness and shape, and the side is polished with a rotary grindstone to produce a puff.
  • NBR acrylonitrile-butadiene copolymer rubber
  • a rubber latex composition was prepared according to the following formulation. From the obtained rubber latex composition, a vulcanized film was produced as follows, and the characteristics were measured. Table 1 shows the measurement results. Formulation Ml.
  • Rubber latex solid content 100 Sulfur 2 Zinc white powder 3 Jetilditi Talented zinc rubamate 1 Mercaptobenzothiazol zinc salt 1 Composition of each rubber latex so that the dry thickness is about 0.5 mm on a glass plate The material was cast, air-dried, and peeled off from the glass plate to obtain a non-flowable film.
  • Vulcanization was performed in an oven at 110 ° C. for 30 minutes.
  • a 5 Omm long marked line is drawn on a strip-shaped test piece cut from the film, and this test piece is immersed in toluene and allowed to stand at room temperature for 5 hours. Then the test piece Take out, measure the length of the marked line, and display the percentage of extension to the original marked line length in%.
  • the strain-stress curve was automatically recorded at a tensile speed of 50 Omm / min, and the stress at a given elongation, elongation at break (%) and breaking strength (kgZcm 2 ) were determined. I read.
  • the stress at a predetermined elongation is expressed as 100% modulus (kg / cm2) in the case of a stress at 100% elongation.
  • the uniformity of foam in the foam was visually observed, and the following five-stage evaluation was performed.
  • a 38 mm diameter disk is punched from the foam, its weight is measured and divided by volume.
  • a test piece obtained by punching the foam with a No. 2 dumbbell (distance between marked lines: 2 Omm) was pulled at a pulling speed of 50 OmmZm in, and the strength at break (kgZcm2) and elongation (% ) was measured.
  • NBR latex prepared in Example 1, as a thiol compound, thiodalicholic acid and ethylene darikol bisthiodali cholate were used in 6 parts and 1.8 parts (double bond, respectively) with respect to 100 parts of solid content of the latex. The number of moles used per 100 was 7.9 and 1.0, respectively.) The reaction was carried out in the same manner as in Example 1 except that thiol-modified NBR latex (Lx7) was used.
  • the NBR latex composition (Example 3) in which 2 parts of sulfur and 3 parts of zinc white were blended with 100 parts of the solid rubber content of the latex (Lx 7) and the solid of the unmodified NBR latex (Lx 6) of Comparative Example 1 2 parts sulfur and zinc for 100 parts rubber
  • a rubber latex composition (Comparative Example 3) containing 3 parts of white flower was prepared, and a vulcanized film was prepared in the same manner as in Example 1 (vulcanization conditions: 100 minutes at 100 ° C.). Was evaluated.
  • Table 3 shows the evaluation results together with the addition rate of the thiol compound.
  • Example 3 Using the thiol-modified NBR latex (Lx7) prepared in Example 3, a foam was produced in the same manner as in Example 2. This foam was equivalent to the foam of the present invention produced in Example 2. Industrial applicability
  • the rubber foam produced from the thiol-modified rubber latex of the present invention has excellent elasticity and soft feel, and has high strength.
  • the rubber foam produced from the thiol-modified rubber latex of the present invention is useful for applications requiring a high balance between elasticity and strength. Particularly, it is suitable as a puff for cosmetics, a sponge mouth, and the like.

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  • Chemical & Material Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne un latex de caoutchouc diénique conjugué, auquel est lié, par l'intermédiaire du groupe thiol, un composé mercapto de la formule générale (1): (HS-R1-M)n-R?2, où R1¿ représente un groupe hydrocarbure C¿1?-C10; M représente -CO2-, ou -SO3-; n est un entier compris entre 1 et 6; et lorsque n vaut 1, R?2¿ représente hydrogène, un métal alcalin, -NR¿4? (R représente H, alkyle ou hydroxyalkyle), alkyle ou alcoxyalkyle, et lorsque n est compris entre 2 et 6, R?2¿ représente un groupe organique C¿2?-C18 ou un groupe hétérocyclique C2-C5. Ce latex peut être utilisé comme matière première pour la production de mousse.
PCT/JP1997/003864 1996-10-25 1997-10-24 Latex de caoutchouc dienique conjugue, composition de latex de caoutchouc, et caoutchouc cellulaire Ceased WO1998018860A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP1998520275A JP4049819B6 (ja) 1996-10-25 1997-10-24 共役ジエン系重合体ゴムラテックス組成物およびゴム発泡体

Applications Claiming Priority (2)

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JP8/299899 1996-10-25
JP29989996 1996-10-25

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WO1998018860A1 true WO1998018860A1 (fr) 1998-05-07

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006057343A1 (fr) * 2004-11-26 2006-06-01 Bridgestone Corporation Latex de caoutchouc naturel modifie et son procede de production, caoutchouc naturel modifie et son procede de production, composition de caoutchouc et pneu
WO2010035808A1 (fr) * 2008-09-25 2010-04-01 株式会社ブリヂストン Composition thermodurcissable
JP2015063648A (ja) * 2013-08-26 2015-04-09 横浜ゴム株式会社 ゴム組成物およびこれを用いる空気入りタイヤ
WO2015147179A1 (fr) * 2014-03-27 2015-10-01 横浜ゴム株式会社 Composition de caoutchouc et pneu l'utilisant
KR20190064758A (ko) 2017-12-01 2019-06-11 주식회사 엘지화학 니트릴계 고무 조성물 제조방법, 니트릴계 고무 라텍스 조성물 및 발포 성형체
WO2019151020A1 (fr) * 2018-01-31 2019-08-08 日本ゼオン株式会社 Latex de caoutchouc mousse
JP2023015945A (ja) * 2021-07-20 2023-02-01 株式会社ブリヂストン 変性共役ジエン系重合体、ゴム組成物、及びタイヤ

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0614811A (ja) * 1992-07-01 1994-01-25 Inoac Corp パフ用基材の製造方法
JPH0630816A (ja) * 1992-07-10 1994-02-08 Inoac Corp パフ用基材の製造方法
JPH08134251A (ja) * 1994-11-09 1996-05-28 Nishikawa Rubber Co Ltd ラテックススポンジゴム組成物

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0614811A (ja) * 1992-07-01 1994-01-25 Inoac Corp パフ用基材の製造方法
JPH0630816A (ja) * 1992-07-10 1994-02-08 Inoac Corp パフ用基材の製造方法
JPH08134251A (ja) * 1994-11-09 1996-05-28 Nishikawa Rubber Co Ltd ラテックススポンジゴム組成物

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006057343A1 (fr) * 2004-11-26 2006-06-01 Bridgestone Corporation Latex de caoutchouc naturel modifie et son procede de production, caoutchouc naturel modifie et son procede de production, composition de caoutchouc et pneu
US8039546B2 (en) 2004-11-26 2011-10-18 Bridgestone Corporation Modified natural rubber latex and method for producing the same, modified natural rubber and method for producing the same, rubber composition and tire
WO2010035808A1 (fr) * 2008-09-25 2010-04-01 株式会社ブリヂストン Composition thermodurcissable
US8541510B2 (en) 2008-09-25 2013-09-24 Bridgestone Corporation Thermosetting composition
JP5647000B2 (ja) * 2008-09-25 2014-12-24 株式会社ブリヂストン 熱硬化性組成物
JP2015063648A (ja) * 2013-08-26 2015-04-09 横浜ゴム株式会社 ゴム組成物およびこれを用いる空気入りタイヤ
WO2015147179A1 (fr) * 2014-03-27 2015-10-01 横浜ゴム株式会社 Composition de caoutchouc et pneu l'utilisant
JP2015189833A (ja) * 2014-03-27 2015-11-02 横浜ゴム株式会社 ゴム組成物及びこれを用いる空気入りタイヤ
CN106068300A (zh) * 2014-03-27 2016-11-02 横滨橡胶株式会社 橡胶组合物及使用了该橡胶组合物的充气轮胎
CN106068300B (zh) * 2014-03-27 2018-04-03 横滨橡胶株式会社 橡胶组合物及使用了该橡胶组合物的充气轮胎
KR20190064758A (ko) 2017-12-01 2019-06-11 주식회사 엘지화학 니트릴계 고무 조성물 제조방법, 니트릴계 고무 라텍스 조성물 및 발포 성형체
KR102416637B1 (ko) * 2017-12-01 2022-07-01 주식회사 엘지화학 니트릴계 고무 조성물 제조방법, 니트릴계 고무 라텍스 조성물 및 발포 성형체
WO2019151020A1 (fr) * 2018-01-31 2019-08-08 日本ゼオン株式会社 Latex de caoutchouc mousse
JP2023015945A (ja) * 2021-07-20 2023-02-01 株式会社ブリヂストン 変性共役ジエン系重合体、ゴム組成物、及びタイヤ

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