WO2015136792A1 - Composition de caoutchouc et produit vulcanisé obtenu à partir de celle-ci - Google Patents

Composition de caoutchouc et produit vulcanisé obtenu à partir de celle-ci Download PDF

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Publication number
WO2015136792A1
WO2015136792A1 PCT/JP2014/081842 JP2014081842W WO2015136792A1 WO 2015136792 A1 WO2015136792 A1 WO 2015136792A1 JP 2014081842 W JP2014081842 W JP 2014081842W WO 2015136792 A1 WO2015136792 A1 WO 2015136792A1
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mass
black
rubber composition
parts
olefin
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PCT/JP2014/081842
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English (en)
Japanese (ja)
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小林　直紀
阿部　靖
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電気化学工業株式会社
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Priority to JP2016507270A priority Critical patent/JPWO2015136792A1/ja
Publication of WO2015136792A1 publication Critical patent/WO2015136792A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/16—Elastomeric ethene-propene or ethene-propene-diene copolymers, e.g. EPR and EPDM rubbers
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/37—Thiols
    • C08K5/375—Thiols containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L11/00—Compositions of homopolymers or copolymers of chloroprene

Definitions

  • the present invention relates to a rubber composition and a vulcanized product thereof. More specifically, the present invention relates to a rubber composition containing polychloroprene and a vulcanized product thereof.
  • Polychloroprene has excellent mechanical properties, weather resistance and flame retardancy, and is widely used as a material for industrial rubber parts.
  • the performance required for industrial rubber parts has been remarkably increased, and rubber with improved mechanical properties such as tensile stress, tensile strength and elongation at break of polychloroprene vulcanizate, as well as improved ozone resistance Compositions have been sought.
  • a chloroprene elastomer composition (see Patent Document 1) in which polychloroprene sol and polychloroprene gel are mixed at a specific ratio, xanthogen-modified polychloroprene and / or A rubber composition (see Patent Document 2) is known in which sulfur-modified polychloroprene is mixed with mercaptan-modified polychloroprene at a specific ratio, and specific carbon black is further added.
  • a rubber composition containing a specific amount of ethylene-propylene-diene copolymer rubber blended with chloroprene rubber and further containing a specific amount of a thiazole compound, a thiuram compound and a thiourea compound (Patent Document 3) See).
  • Patent Documents 1 and 2 described above are improved in mechanical properties, the ozone resistance is not sufficiently improved.
  • the rubber composition described in Patent Document 3 is resistant to Although the improvement in ozone is high, the mechanical strength is not sufficiently improved.
  • the present invention provides a rubber composition and a vulcanized product thereof that can provide a vulcanized product with improved mechanical properties such as tensile stress, tensile strength, and elongation at break, and significantly improved ozone resistance.
  • the main purpose is to provide a rubber composition and a vulcanized product thereof that can provide a vulcanized product with improved mechanical properties such as tensile stress, tensile strength, and elongation at break, and significantly improved ozone resistance.
  • the rubber composition according to the present invention comprises 100 parts by mass of polychloroprene, 3 to 50 parts by mass of an ethylene / ⁇ -olefin / non-conjugated polyene copolymer, 10 to 100 parts by mass of carbon black, and the ethylene / ⁇ -olefin.
  • non-conjugated polyene copolymer has the chemical formula I (in the chemical formula I, R is an alkyl group having 1 to 20 carbon atoms, n and n 'are the same or different integers of 1 to 8, and p is 1 to 20 parts by mass of a poly (alkylphenol) polysulfide having a structure represented by the formula:
  • R is an alkyl group having 1 to 20 carbon atoms
  • p is 1 to 20 parts by mass of a poly (alkylphenol) polysulfide having a structure represented by the formula:
  • the ethylene / ⁇ -olefin / non-conjugated polyene copolymer those containing 1 to 10% by mass of non-conjugated polyene units in 100% by mass of the ethylene / ⁇ -olefin / non-conjugated polyene copolymer can be used. .
  • Non-conjugated polyene units of the ethylene / ⁇ -olefin / non-conjugated polyene copolymer include 5-ethylidene-2-norbornene, dicyclopentadiene, 5-vinyl-2-norbornene, 7-methyl-1,6-octadiene and At least one selected from 5-methyl-1,4-hexadiene can be used.
  • the alkylphenol structure of the poly (alkylphenol) polysulfide is p-cresol, i-propylphenol, pt-butylphenol, amylphenol, pt-octylphenol, nonylphenol, dodecylphenol, allylphenol, cyclohexylphenol, 4,6- At least one selected from dioctyl resorcin can be used.
  • the carbon black is a furnace carbon black such as SAF (Super Abrasion Furnace Black), ISAF (Intermediate Super Abrasion Furnace Black), IISA (Intermediate ISAF), HAF (High Abrasion Furnace Black), MAF (Medium Abrasion Furnace Black), FEF ( Fast Extruding Furnace Black), SRF (Semi-Reinforcing Furnace Black), GPF (General Purpose Furnace Black), FF (Fine Furnace Black) and CF (Conductive Furnace Black), FT (Fine Thermal Black) and MT (thermal carbon black) Medium thermal black), channel carbon black, at least one selected from EPC (Easy Processing Channel Black), MPC (Medium Processing Channel Black), and acetylene black can be used.
  • the vulcanized product according to the present invention is obtained by vulcanizing the rubber composition described above.
  • a rubber composition from which a vulcanizate having improved mechanical properties such as tensile stress, tensile strength and elongation at break and further improved ozone resistance can be obtained, and a vulcanizate thereof. it can.
  • the rubber composition of the present embodiment comprises (1) polychloroprene, (2) ethylene / ⁇ -olefin / non-conjugated polyene copolymer, (3) carbon black, and (4) poly (alkylphenol) having a specific structure. It contains polysulfide.
  • Polychloroprene is obtained by polymerizing chloroprene and then washing and drying as necessary.
  • emulsifiers, dispersants, catalysts, catalyst activators, chain transfer agents and polymerizations added during the polymerization May contain banners.
  • Monomers copolymerizable with chloroprene include acrylic acid esters such as methyl acrylate, butyl acrylate and 2-ethylhexyl acrylate, and methacrylic acid esters such as methyl methacrylate, butyl methacrylate and 2-ethylhexyl methacrylate.
  • Hydroxy (meth) acrylates such as 2-hydroxyethyl (meth) acrylate, 2-hydroxymethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate, and 2,3-dichloro-1,3-butadiene, There are 1-chloro-1,3-butadiene, butadiene, isoprene, ethylene, styrene and acrylonitrile.
  • the monomer copolymerized with chloroprene is not limited to one type, and a copolymer obtained by copolymerizing three or more types of monomers including chloroprene can also be used. Further, the polymer structure of the obtained polychloroprene is not particularly limited.
  • Polychloroprene is classified into sulfur-modified polychloroprene, mercaptan-modified polychloroprene, and xanthogen-modified polychloroprene.
  • the sulfur-modified polychloroprene is obtained by copolymerizing a raw material monomer containing chloroprene as a main component and sulfur, and plasticizing the obtained copolymer with thiuram disulfide to adjust to a predetermined Mooney viscosity.
  • Mercaptan-modified polychloroprene is obtained by using alkyl mercaptans such as n-dodecyl mercaptan, tert-dodecyl mercaptan and octyl mercaptan as molecular weight modifiers.
  • Xanthogen-modified polychloroprene is obtained by using an alkyl xanthogen compound as a molecular weight modifier.
  • the polychloroprene blended in the rubber composition may be any of the above-mentioned various polychloroprenes, and in particular, when improving heat resistance, use non-sulfur-modified polychloroprene such as mercaptan-modified polychloroprene or xanthogen-modified polychloroprene. Is preferred.
  • Ethylene / ⁇ -olefin / non-conjugated polyene copolymer is a tensile stress, tensile strength, vulcanized product obtained by vulcanizing a rubber composition, Blended to improve mechanical properties such as elongation at break and ozone resistance.
  • Ethylene / ⁇ -olefin / non-conjugated polyene copolymer is produced by copolymerizing ethylene with ⁇ -olefin and non-conjugated polyene by a conventionally known method such as a gas phase polymerization method, a solution polymerization method or a slurry polymerization method. can do.
  • the ⁇ -olefin constituting the ethylene / ⁇ -olefin / non-conjugated polyene copolymer is not particularly limited, but from the viewpoint of processability, it has 3 to 20 carbon atoms. ⁇ -olefins are preferred. Examples of the ⁇ -olefin having 3 to 20 carbon atoms include propylene, 1-butene, 1-pentene, 1-hexene, 1-heptene, 1-octene and 1-decene.
  • ⁇ -olefins propylene, 1-butene, 1-hexene and 1-octene are preferable, and propylene is particularly preferable from the viewpoint of a balance between processability and heat-resistant physical properties.
  • the ⁇ -olefin constituting the ethylene / ⁇ -olefin copolymer and the ethylene / ⁇ -olefin / non-conjugated polyene copolymer is not limited to one type, but two or more types of ⁇ -olefin are copolymerized. It may be.
  • Non-conjugated polyene examples include 5-ethylidene-2-norbornene, dicyclopentadiene, 5-propylidene-2-norbornene, 5 -Cyclic polyenes such as vinyl-2-norbornene, 2,5-norbornadiene, 1,4-cyclohexadiene, 1,4-cyclooctadiene and 1,5-cyclooctadiene, 1,4-hexadiene, 4-methyl- 1,4-hexadiene, 5-methyl-1,4-hexadiene, 5-methyl-1,5-heptadiene, 6-methyl-1,5-heptadiene, 6-methyl-1,6-octadiene, 7-methyl- 1,6-octadiene, 5,7-dimethyl-1,6-octa
  • non-conjugated polyenes from the viewpoint of crosslinking efficiency, 5-ethylidene-2-norbornene, dicyclopentadiene, 5-vinyl-2-norbornene, 7-methyl-1,6-octadiene and 5-methyl-1, 4-hexadiene is preferred, and 5-ethylidene-2-norbornene is particularly preferred.
  • the non-conjugated polyene constituting the ethylene / ⁇ -olefin / non-conjugated polyene copolymer is not limited to one type, and two or more types of non-conjugated polyenes may be copolymerized.
  • the amount of non-conjugated polyene constituting the ethylene / ⁇ -olefin / non-conjugated polyene copolymer is 1 to 10% by mass of non-conjugated polyene units in 100% by mass of the ethylene / ⁇ -olefin / non-conjugated polyene copolymer. It can be. By adjusting the bonding amount of the non-conjugated polyene unit within this range, the mechanical properties of the obtained vulcanizate are further improved.
  • the blending amount of the ethylene / ⁇ -olefin / non-conjugated polyene copolymer is 3 to 50 parts by mass per 100 parts by mass of polychloroprene. If the blending amount of the ethylene / ⁇ -olefin / non-conjugated polyene copolymer is less than 3 parts by mass, the resulting vulcanizate may not exhibit sufficient ozone resistance. Further, when the blending amount of the ethylene / ⁇ -olefin / non-conjugated polyene copolymer exceeds 50 parts by mass, the mechanical strength of the obtained vulcanizate is lowered.
  • the blending amount of the ethylene / ⁇ -olefin / non-conjugated polyene copolymer is preferably 5 to 40 parts by mass, more preferably 10 to 30 parts by mass.
  • Carbon black is blended in order to improve mechanical properties such as tensile stress, tensile strength, and elongation at break of a vulcanized product obtained by vulcanizing a rubber composition.
  • carbon black any of furnace black by incomplete combustion method, thermal black by thermal decomposition method, channel black, and acetylene black can be used.
  • SAF Super Abrasion Furnace Black
  • ISAF Intermediate Super Abrasion Furnace Black
  • IISA Intermediate ISAF
  • HAF High Abrasion Furnace Black
  • MAF Medium Abrasion Furnace Black
  • FEF Flud Extruding Furnace Black
  • SRF Semi-Reinforcing Furnace Black
  • GPF General Purpose Furnace Black
  • FF Fluorine Furnace Black
  • CF Conductive Furnace Black
  • Thermal blacks include FT (Fine Thermal Black) and MT (Medium Thermal Black).
  • Channel black includes EPC (Easy Processing Channel Black), MPC (Medium Processing Channel Black), and acetylene black.
  • acetylene black is preferably used from the viewpoint of improving the heat resistance of the resulting vulcanizate.
  • the blending amount of carbon black is 10 to 100 parts by mass per 100 parts by mass of polychloroprene. If the blending amount of the carbon black is less than 10 parts by mass, the reinforcing property when the rubber composition is vulcanized may be reduced, and the vulcanized product may be impractical. If the amount of carbon black exceeds 100 parts by mass, the heat resistance of the rubber composition may be drastically reduced.
  • the amount of carbon black is preferably 15 to 80 parts by mass, more preferably 20 to 60 parts by mass.
  • Poly (alkylphenol) polysulfide improves the mechanical properties of rubber compositions by vulcanizing polychloroprene and ethylene / ⁇ -olefin / non-conjugated polyene copolymers in the rubber composition.
  • the type of poly (alkylphenol) polysulfide compounded in the rubber composition is not particularly limited, but from the viewpoint of improving mechanical properties, the alkylphenol skeleton is p-cresol, i-propylphenol, pt-butylphenol. , Amylphenol, pt-octylphenol, nonylphenol, dodecylphenol, allylphenol, cyclohexylphenol, and 4,6-dioctylresorcinol.
  • the compounding amount of poly (alkylphenol) polysulfide is 1 to 20 parts by mass per 100 parts by mass of the ethylene / ⁇ -olefin / non-conjugated polyene copolymer in the rubber composition. If the blending amount of the poly (alkylphenol) polysulfide is less than this range, the mechanical strength of the resulting vulcanizate may not be sufficiently developed. Moreover, when the compounding quantity of poly (alkylphenol) polysulfide exceeds this range, the heat resistance of the obtained vulcanizate will fall.
  • the blending amount of poly (alkylphenol) polysulfide is preferably 2 to 15 parts by mass, more preferably 3 to 10 parts by mass.
  • the rubber composition can be obtained by kneading each of the above-described compounds using an open roll, a Banbury mixer, an extruder, or the like at a vulcanization temperature or lower. At this time, after kneading (2) ethylene / ⁇ -olefin / non-conjugated polyene copolymer and (4) poly (alkylphenol) polysulfide, (1) adding polychloroprene and (3) carbon black and kneading, This is desirable because the mechanical properties of the resulting vulcanizate are further improved.
  • the rubber composition contains a vulcanizing agent, a vulcanization accelerator, a scorch inhibitor, a processing aid, etc. that are usually used in the rubber industry as long as the effects of the present invention are not impaired. be able to.
  • the rubber composition of the present embodiment contains a specific amount of polychloroprene, a specific amount of ethylene / ⁇ -olefin / non-conjugated polyene copolymer, carbon black, and poly (alkylphenol) polysulfide. Therefore, a rubber composition having not only excellent mechanical properties such as tensile stress, tensile strength and elongation at break of the vulcanizate but also extremely excellent ozone resistance can be obtained.
  • Vulcanized material The vulcanized material of the present embodiment is obtained by molding and vulcanizing the rubber composition described above into a shape suitable for the purpose.
  • the vulcanization method of the rubber composition is not particularly limited, and during or after molding, press vulcanization, injection vulcanization, direct kettle vulcanization, indirect kettle vulcanization, direct steam continuous vulcanization, Vulcanization may be performed by a vulcanization method such as normal pressure continuous vulcanization or continuous vulcanization press.
  • vulcanization conditions such as vulcanization temperature and vulcanization time are not particularly limited, and can be set as appropriate.
  • the vulcanization temperature is preferably 130 to 200 ° C, more preferably 140 to 190 ° C.
  • machining safety is a machining characteristic evaluated by the scorch time, and greatly affects the defect occurrence rate. Specifically, when the scorch time is short, the frequency of occurrence of defective molding is increased because the unvulcanized rubber component is vulcanized during molding at a high temperature.
  • the vulcanized product of the present embodiment uses the rubber composition described above, the vulcanized product has a tensile stress, tensile strength, elongation at break, and ozone resistance as compared with a vulcanized product using conventional polychloroprene. Improve gender comprehensively. For this reason, the vulcanizate of this embodiment has high ozone resistance such as a transmission belt, a conveyor belt, an air spring, an automobile hose, an automobile boot, an anti-vibration rubber as well as a seismic isolation rubber and sponge. It can also be suitably used for required molded articles.
  • Tables 1 to 3 The components shown in Tables 1 to 3 are as follows. (Polychloroprene) ⁇ Mercaptan-modified polychloroprene (S-40V, manufactured by Denki Kagaku Kogyo Co., Ltd.) ⁇ Xanthogen-modified polychloroprene (DCR-66, manufactured by Denki Kagaku Kogyo Co., Ltd.) ⁇ Sulfur modified polychloroprene (DCR-107, manufactured by Denki Kagaku Kogyo Co., Ltd.)
  • Carbon black Carbon black
  • HAF Alignment Agent
  • GPF Carbon black GPF
  • SRF Alignment Reduction Function
  • Poly (alkylphenol) polysulfide) ⁇ Poly (t-butylphenol) polysulfide (Altema VultacTB7) ⁇ Poly (t-amylphenol) disulfide (Sunshine AP manufactured by Sanshin Chemical Industry Co., Ltd.)
  • Example 1 The rubber composition of Example 1 is composed of 100 parts by mass of mercaptan-modified polychloroprene, 30 parts by mass of an ethylene / ⁇ -olefin / non-conjugated polyene copolymer containing 8% by mass of 5-ethylidene-2-norbornene, and 40 parts by mass of carbon black HAF.
  • thiourea vulcanization accelerator as a vulcanization accelerator (Kawaguchi Chemical Industry stock Company Axel 22S: Ethylenethiourea) 0.8 parts by mass, zinc oxide (2 types of zinc oxide manufactured by Sakai Chemical Industry Co., Ltd.) 5 parts by mass, and then kneaded using an 8-inch roll It is.
  • the amount of poly (t-butylphenol) polysulfide added corresponds to 10 parts by mass with respect to 100 parts by mass of the ethylene / ⁇ -olefin / non-conjugated polyene copolymer.
  • the obtained rubber composition was vulcanized at 160 ° C. for 20 minutes with a hydraulic press, and formed into a sheet having a thickness of 2 mm to prepare a test piece. And using this test piece, "tensile stress”"tensilestrength””breakingelongation”,”durometer hardness (HS)", and "ozone resistance” were evaluated.
  • Elastic modulus (durometer hardness (HS)) Based on JIS K6253, it measured using the type D durometer.
  • Ozone resistance According to JIS K6258, evaluated under the conditions of 0 to 20% dynamic elongation, 40 ° C. ⁇ 50 pphm, 144 hours. It was.
  • the vulcanizate using the rubber composition of Example 1 had improved ozone resistance as well as mechanical properties such as tensile stress, tensile strength, and elongation at break.
  • Examples 2 to 18 and Comparative Examples 1 to 5 The formulation of the compound added when preparing the rubber composition was changed as shown in Tables 1 to 3, and the rubber composition was prepared and vulcanized in the same manner as in Example 1. did. The obtained vulcanized samples were evaluated in the same manner as in Example 1 for “tensile stress”, “tensile strength”, “breaking elongation”, “durometer hardness (HS)”, and “ozone resistance”. The evaluation results are shown in Tables 1 to 3.
  • a rubber composition capable of obtaining a vulcanizate having improved ozone resistance as well as mechanical properties such as tensile stress, tensile strength and elongation at break was obtained.
  • the vulcanizate obtained by vulcanizing this rubber composition has improved properties as described above, and can be suitably used as a material for industrial products.

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  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • Polymers & Plastics (AREA)
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Abstract

Cette invention concerne : une composition de caoutchouc permettant d'obtenir un produit vulcanisé ayant d'excellentes propriétés mécaniques telles qu'une résistance à la traction, un allongement à la rupture, une résistance à la déchirure, et une force élastique du produit vulcanisé qui sont excellents ; et un produit vulcanisé obtenu à partir de celle-ci. La composition de caoutchouc contient 100 parties en poids du polychloroprène, de 3 à 50 parties en poids d'un copolymère d'éthylène-α-oléfine-polyène non conjugué, de 10 à 100 parties en poids de noir de carbone, et 1 à 20 parties en poids, pour 100 parties en poids d'éthylène-alpha-oléfine-polyène non conjugué, d'un poly(alkylphénol)polysulfure ayant une structure représentée par la formule chimique I (dans la formule chimique I, R représente un groupe alkyle C1 -20, n et n' représentent des nombres entiers de 1 à 8 identiques ou différents, et p représente un nombre entier de 0 à 50.
PCT/JP2014/081842 2014-03-12 2014-12-02 Composition de caoutchouc et produit vulcanisé obtenu à partir de celle-ci WO2015136792A1 (fr)

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WO2017086282A1 (fr) * 2015-11-16 2017-05-26 デンカ株式会社 Améliorant pour composition à base de caoutchouc, vulcanisat de caoutchouc auquel est ajouté un améliorant, et article moulé
RU2692316C1 (ru) * 2018-06-20 2019-06-24 федеральное государственное унитарное предприятие "Федеральный научно-производственный центр "Прогресс" (ФГУП "ФНПЦ "Прогресс") Огнестойкая резиновая смесь с улучшенными антифрикционными свойствами
WO2020045454A1 (fr) * 2018-08-30 2020-03-05 住友化学株式会社 Composition de caoutchouc, corps moulé composite métal-caoutchouc et procédé de fabrication d'un corps moulé composite métal-caoutchouc
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Cited By (11)

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Publication number Priority date Publication date Assignee Title
WO2017086282A1 (fr) * 2015-11-16 2017-05-26 デンカ株式会社 Améliorant pour composition à base de caoutchouc, vulcanisat de caoutchouc auquel est ajouté un améliorant, et article moulé
CN108350230A (zh) * 2015-11-16 2018-07-31 电化株式会社 橡胶系组合物改性剂、及添加有该改性剂的橡胶组合物的硫化物以及成形品
CN108350230B (zh) * 2015-11-16 2020-10-20 电化株式会社 橡胶系组合物改性剂、及添加有该改性剂的橡胶组合物的硫化物以及成形品
US10882985B2 (en) 2015-11-16 2021-01-05 Denka Company Limited Rubber-based composition modifier, and vulcanizate and molded product of rubber composition containing the rubber-based composition modifier
KR20200024865A (ko) * 2017-06-29 2020-03-09 알케마 인코포레이티드 오가노폴리설파이드로 안정화된 중합체 조성물
JP2020526606A (ja) * 2017-06-29 2020-08-31 アーケマ・インコーポレイテッド オルガノポリスルフィドによって安定化されたポリマー組成物
JP7181234B2 (ja) 2017-06-29 2022-11-30 アーケマ・インコーポレイテッド オルガノポリスルフィドによって安定化されたポリマー組成物
KR102584689B1 (ko) 2017-06-29 2023-10-10 알케마 인코포레이티드 오가노폴리설파이드로 안정화된 중합체 조성물
RU2692316C1 (ru) * 2018-06-20 2019-06-24 федеральное государственное унитарное предприятие "Федеральный научно-производственный центр "Прогресс" (ФГУП "ФНПЦ "Прогресс") Огнестойкая резиновая смесь с улучшенными антифрикционными свойствами
WO2020045454A1 (fr) * 2018-08-30 2020-03-05 住友化学株式会社 Composition de caoutchouc, corps moulé composite métal-caoutchouc et procédé de fabrication d'un corps moulé composite métal-caoutchouc
CN116144123A (zh) * 2023-02-22 2023-05-23 湖北辰诺医药包装科技有限公司 一种体外诊断试剂用氯化丁基橡胶塞及其制备方法

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