WO2001074940A1 - Nitrile rubber composition and vulcanized rubber article - Google Patents
Nitrile rubber composition and vulcanized rubber article Download PDFInfo
- Publication number
- WO2001074940A1 WO2001074940A1 PCT/JP2001/002022 JP0102022W WO0174940A1 WO 2001074940 A1 WO2001074940 A1 WO 2001074940A1 JP 0102022 W JP0102022 W JP 0102022W WO 0174940 A1 WO0174940 A1 WO 0174940A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- rubber
- rubber composition
- sulfonic acid
- composition according
- weight
- 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
Links
Classifications
-
- 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
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S525/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S525/942—Polymer derived from nitrile, conjugated diene and aromatic co-monomers
Definitions
- the present invention relates to a nitrile rubber composition excellent in heat aging resistance and a vulcanized rubber article obtained by vulcanizing the nitrile rubber composition.
- Nitrile rubber represented by acrylonitrile-butadiene copolymer rubber (NBR) has been used as an oil-resistant rubber in the manufacture of rubber articles in various fields such as seals, hoses and belts. Further, hydrogenated NBR has been developed based on market requirements for heat aging resistance and high strength, and the field of use of nitrile rubber has been further expanded.
- Hydrogenated NBR is a hydrogenated butadiene unit in the molecular chain.
- the absence or extremely small number of unsaturated bonds (double bonds) significantly reduces oxidation resistance and heat resistance. It is highly evaluated as an aging rubber.
- Japanese Unexamined Patent Publication (Kokai) No. 11-239,039 discloses that a strong base and a strong salt group are used to improve the heat aging resistance of a hydrogenated NBR (synonymous with the heat aging resistance in a heated air atmosphere).
- a method of blending a salt of acetic acid with a weak acid or a salt of a weak acid is disclosed.
- ultimate elongation the decrease in elongation at break after heat aging
- An object of the present invention is to reduce the decrease in tensile strength and elongation even under a heated air atmosphere. It is an object of the present invention to provide a nitrile rubber composition which is used as a material for a rubber article.
- the present inventors have conducted intensive studies to achieve the above object, and as a result, have found that it is effective to add nitrile rubber and an organic sulfonate, and have completed the present invention.
- a rubber composition containing 100 parts by weight of nitrile rubber and 0.5 to 20 parts by weight of an organic sulfonate, and a vulcanization obtained by vulcanizing the rubber composition A rubber article is provided.
- the nitrile rubber used in the present invention is a copolymer rubber of an ⁇ , -ethylenically unsaturated nitrile monomer ( a ) and another monomer (b).
- Examples of the monomer (a) include acrylonitrile, methacrylonitrile, ⁇ -chloroacrylonitrile, and the like. Among them, acrylonitrile is preferred. These may be used in combination of two or more.
- the content of the monomer (a) unit in the nitrile rubber is preferably from 10 to 60% by weight, more preferably from 12 to 55% by weight, and still more preferably from 15 to 50% by weight. It is.
- Examples of the other monomer (b) to be copolymerized with the monomer (a) include a conjugated or non-conjugated gen-based monomer and ⁇ - olefin.
- a copolymer rubber having a high iodine value is often obtained, but if necessary, the carbon content of the copolymer rubber may be increased.
- the carbon unsaturated bond may be hydrogenated by a known method to obtain a hydrogenated product, so that the iodine value may be lowered.
- conjugated diene monomer examples include 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene and 1,3-pentadiene, and among them, 1,3-butadiene is preferable.
- Nitrile rubber is obtained by copolymerizing monomer (a), co-generator monomer and other copolymerizable monomers as required, and hydrogenating as necessary.
- the total amount of the non-hydrogenated conjugated diene monomer units and the hydrogenated conjugated diene monomer units in the copolymer is preferably 40 to 90% by weight / 0 , more preferably Is 45-88% by weight. More preferably, it is 50 to 85% by weight.
- the non-conjugated diene monomer preferably has 5 to 12 carbon atoms, and examples thereof include 1,4-pentadiene, 1,4-hexadiene, vinyl / leno / levonolenene, and dicyclopentane.
- ⁇ -olefin those having 2 to 12 carbon atoms are preferable, and examples thereof include ethylene, propylene, 1-butene, 4-methylenol-one-pentene, 1-hexene, and 1-octene.
- Other monomers include ⁇ , / 3-ethylenically unsaturated carboxylic acid esters, aromatic vinyl monomers, fluorine-containing vinyl monomers, ⁇ , —ethylenically unsaturated monocarboxylic acids, a , j3-ethylenically unsaturated dicarboxylic acid anhydrides and copolymerizable antioxidants.
- a, iS-ethylenically unsaturated carboxylic acid esters include (meth) acrylates such as methyl acrylate, n-ethyl acrylate, n-butyl acrylate, n-dodecyl acrylate, methyl methacrylate, and ethyl methacrylate.
- Acrylates having an alkyl group having 1 to 18 carbon atoms alkoxyalkyl (meth) acrylates such as methoxymethyl phthalate, methoxymethyl methacrylate, methoxethyl methacrylate and the like; An alkyl group having 2 to 12 carbon atoms; a cyanoalkyl (meth) acrylate such as ⁇ -cyanoethyl acrylate, ⁇ -cyanoethyl acrylate, or cyanobutyl methacrylate, Cyanoalkyl groups having 2 to 12 carbon atoms; 2-hydroxyethylacrylic Hydroxyalkyl (meth) acrylates such as 2-hydroxyhexyl methacrylate and hydroxypropyl acrylate, wherein the hydroxyalkyl group has 1 to 12 carbon atoms; ⁇ ,] 3-Ethylene, such as monoethyl oleate, dimethyl maleate, dimethyl fumarate, dimethyl itaconate, getylene
- Amino group-containing monomers such as methyl acrylate and getyl aminoethyl acrylate; ⁇ -ethylenically unsaturated carboxylic acid ester monomers; fluoroalkyl groups such as trifluoroethyl acrylate and tetrafluoropropyl methacrylate (Meta) acrylate; fluorobenzyl acrylate; Ruo b benzyl methacrylate click Examples include fluorine-substituted benzyl (meth) acrylates such as lylate.
- the aromatic vinyl monomer include styrene, methyl styrene, and bulpyridine.
- fluorine-containing biel-based monomer examples include fluoroethyl vinyl ether, fluoropropyl butyl ether, o-trifluoromethylstyrene, pentafluorobenzoyl butyl, difluoroethylene, tetrafluoroethylene, and the like.
- ⁇ 3-ethylenically unsaturated carboxylic acid examples include acrylic acid, methacrylic acid, itaconic acid, fumaric acid, maleic acid, and maleic anhydride.
- Examples of the copolymerizable antioxidants include N— (4-anilinophenyl) acrylamide, N- (4-anilinophenyl) methacrylamide, N— (4-anilinophenyl) cinnamamide, and N— ( 4-anilinophenyl) crotonamide, N-phenyl 4- (3-butylbenzyloxy) aniline, N-phenyl 41- (4-vinyl benzyl / reoxy) aniline and the like.
- a plurality of these copolymerizable monomers may be used in combination.
- the Mooney viscosity (ML 1 + 4 , 100 ° C.) (measured according to JISK630) of the nitrile rubber used in the present invention is not particularly limited, and is preferably 20 to 140, More preferably, it is 30 to 120. If the Mooney viscosity is too low, the strength properties will be poor, and if the Mooney viscosity is too high, the processability will be poor.
- the iodine value of the nitrile rubber is also not particularly limited, but is preferably 120 or less, more preferably 60 or less, and still more preferably 30 or less. If the iodine value is too high, the resistance to air heating aging will deteriorate. If the iodine value is too high, the unsaturated bond in the rubber molecular chain may be saturated by performing a hydrogenation reaction.
- the nitrile rubber is usually produced by radical copolymerization of the above monomers or hydrogenation after radical copolymerization.
- the polymerization method may be any of conventionally known methods such as emulsion polymerization, suspension polymerization, and solution polymerization, but emulsion polymerization is particularly preferred.
- Emulsion polymerization is usually carried out by adding a monomer, a polymerization initiator, an emulsifier, a polymerization chain transfer agent and the like to an aqueous medium (usually water).
- aqueous medium usually water.
- the emulsifier include anion type (sulfuric acid ester salt of higher alcohol, alkylbenzene sulfonate, sulfonate of aliphatic carboxylic acid ester, etc.), nonionic type (alkylester type of polyethylene glycol, alkylphenyl ether type).
- amphoteric surfactants carboxylate, sulfate, sulfonate, phosphate, phosphate ester as anion moiety, amine salt, quaternary as cation moiety
- Ammonium salt examples include inorganic peroxides such as hydrogen peroxide and persulfuric acid lime, organic peroxides such as tamenediisopropylbenzene paramenthane, ferrous iron salts, tetraethylene, pentaamine, and the like.
- a redox catalyst in which the above reducing agents are combined.
- the polymerization temperature is preferably 0 to 50 ° C.
- the rubber composition of the present invention comprises the above-mentioned tolyl-based rubber and an organic sulfonate.
- Examples of the organic sulfonic acid salt used in the present invention include an aliphatic sulfonic acid salt, an aromatic sulfonic acid salt, an aliphatic aminoethylsulfonic acid, and a fluorinated aliphatic sulfonic acid salt.
- Aliphatic sulfonates having an alkyl group of from 50 to 50 aromatic sulfonates and aliphatic aminoethylsulfonic acids, and alkyl groups of an aliphatic sulfonate having an alkyl group having from 5 to 50 carbon atoms.
- Fluorinated aliphatic sulfonates in which hydrogen has been partially or completely fluorinated are preferred.
- organic sulfonic acid salt an aromatic sulfonic acid salt, an aliphatic aminoethyl sulfonic acid and the like are preferable, and in particular, an aromatic sulfonic acid salt or an amide sulfonic acid salt having an alkyl group having 5 to 50 carbon atoms.
- the organic sulfonates are preferably alkali metal salts of organic sulfonic acids and ammonium salts of organic sulfonic acids, and organic sulfonates such as lithium salts, sodium salts, potassium salts, rubidium salts and cesium salts. Acid alkali metal salts are more preferred, and organic sulfonic acid sodium salts and organic sulfonic acid lithium salts are particularly preferred.
- organic sulfonates include sodium hexadecylsulfonate, sodium dodecylsulfonate, lithium dodecylsulfonate, and AOS.
- Examples of the metal salt of a fluorinated aliphatic sulfonate in which hydrogen of the alkyl group of an aliphatic sulfonate having an alkyl group having a prime number of 5 to 50 is partially or entirely substituted by fluorine are provided. .
- sodium dodecylbenzenesulfonate, N-methyllauroyltaurine sodium salt and the like are preferable. These can be used alone or in combination of two or more.
- the amount of the organic sulfonate used is preferably 0.5 to 20 parts by weight, more preferably 0.7 to 10 parts by weight, and particularly preferably 100 parts by weight of nitrile rubber. Is a ratio of 1 to 8 parts by weight. If the amount is too small, the heat aging resistance is inferior. If the amount is too large, bloom tends to occur on the surface of the vulcanized rubber article.
- the rubber composition of the present invention can be vulcanized by adding a vulcanizing agent.
- sulfur vulcanizing agent examples include: sulfur; thiuram compounds such as tetramethylthiuram mono or disulfide; morpholine disulfide, 2-
- the amount of the sulfur-based vulcanizing agent used is preferably 0.1 to 10 parts by weight, more preferably 0.2 to 7 parts by weight, in terms of sulfur, based on 100 parts by weight of the nitrile rubber. Particularly preferably, it is 0.3 to 5 parts by weight. If the amount is too small, the vulcanization density decreases, and the compression set increases. If the amount is too large, the bending fatigue resistance may be insufficient or the dynamic heat generation may increase.
- Sulfur-based vulcanizing agents are usually used together with known vulcanizing aids such as zinc white and stearic acid and known vulcanization accelerators such as thiuram-based, guanidine-based, sulfenamide-based, thiazole-based and dithio-rubamic acid-based vulcanizing agents. used.
- known vulcanizing aids such as zinc white and stearic acid
- known vulcanization accelerators such as thiuram-based, guanidine-based, sulfenamide-based, thiazole-based and dithio-rubamic acid-based vulcanizing agents.
- thiuram-based vulcanization accelerator include tetramethyl thiuram disulfide, tetraethyl thiuram di'sulfide, ⁇ , monodimethyl ⁇ , ⁇ 'diphenyl thiuram disulfide and the like.
- Examples of the guadin-based vulcanization accelerator include diph: nildanidine, diortotriluguanidine, orthotrinolebiguanidine and the like.
- Examples of sulfenamide vulcanization accelerators include ⁇ -cyclohexyl-2-benzothiazinoresnolefenamide, ⁇ , N'-diisopropisolate 2-benzothiazylsulfenamide, and ter-butylbutyrene. Examples include 2_benzothiazylsnolefenamide.
- Examples of the thiazole vulcanization accelerator include 2-mercaptobenzothiazole, dibenzothiazyl disulfide and the like.
- Examples of the dithiol-rubic acid-based vulcanization accelerator include tellurium dimethyldithiocarbamate and zinc dimethyldithiocarbamate.
- organic peroxide vulcanizing agent examples include hydroperoxides such as cumene hydroperoxide, diisopropylbenzene hydroperoxide, 2,5-dimethylhexane, and 2,5-dihydroperoxide; Dialkyl peroxides such as dicumyl baroxide, di-tert-butyl peroxide, and t-butyl cumyl peroxide; benzoyl peroxide, 2,4-dichlorobenzene benzoyl peroxide, bis- (3, Diarboxides such as 5,5-trimethylhexanoyl peroxide; 2,5-dimethinolate 2,5-bis (t-butylperoxy) hexane; 1,3-di (t-butylpropyl) (Xiisopropyl) benzene, 2,5-dimethyl-1,2,5-di (t-butynoleoxy) hexine-1,3,5, dimethyl Luoxy ketals
- the amount of the organic peroxide vulcanizing agent used is preferably 100 parts by weight of nitrile rubber. It is preferably 0.18 parts by weight, more preferably 0.3 to 7 parts by weight, particularly preferably 0.5 parts by weight. If the amount is too small, the vulcanization density decreases, and the compression set increases. If the amount is too large, the rubber elasticity may be insufficient.
- Vulcanization aids used with organic peroxides include zinc white and magnesium oxide, as well as co-crosslinking agents such as bullet compounds, acrylic compounds, methacrylic compounds, epoxy compounds and other polyfunctional monomers.
- Can be Examples of the bur compound include digierbenzene and burtoluene.
- the acryl compounds include 2-methoxyl acrylate, 2-bis (4-attalioxypolyethoxyphenyl) propane, and tetraethylene glycol diatari.
- N —methylenebisacrylamide is exemplified.
- the methacrylic compound include methacrylic acid, methyl methacrylate, ethyl methacrylate, ethylene glycolone resin methacrylate, triethylene glycolone resin methacrylate, trimethylolpropane trimethacrylate, and arylglycidyl ether. And the like.
- examples of other polyfunctional monomers include N, N'-m-phenylene bismaleimide, diarinolephthalate, triarinolecinurate, triallyl isosocyanurate, and liquid bead polybutadiene. You.
- the type and amount of the vulcanization aid, vulcanization accelerator, etc. are determined during the production of the rubber composition and the rubber product using the composition, the operability, and the molding and processing safety. It is appropriately selected to satisfy the qualitative and required physical properties.
- the type and amount of the compounding agent other than the organic sulfonate, the vulcanizing agent, the vulcanization aid and the vulcanization accelerator are also not particularly limited, and, if necessary, a range that does not substantially impair the effects of the present invention. It is selected and determined as appropriate.
- Examples of such compounding agents include reinforcing agents such as cellulose black and silica, fillers such as calcium carbonate and clay, softening agents, plasticizers, and anti-aging agents (amine-based anti-aging agents such as octylated diphenylamine). And zinc salts of 2-mercaptobenzimidazole, etc.), stabilizers and processing aids.
- a rubber composition is obtained by mixing and kneading nitrile rubber, vulcanizing agent, organic sulfonic acid salt, and these compounding agents using a kneading machine such as a roll, a Banbury, a kneader, and an internal mixer.
- a kneading machine such as a roll, a Banbury, a kneader, and an internal mixer.
- the lower limit of the temperature during vulcanization is preferably 100 ° C, more preferably 130 ° C, particularly preferably 140 ° C, and the upper limit is preferably 200 ° C. If the temperature is too low, a long vulcanization time may be required or the vulcanization density may be low. If the temperature is too high, molding may fail.
- the vulcanization time varies depending on the vulcanization method, vulcanization temperature, shape and the like, but is preferably in the range of 1 minute to 5 hours from the viewpoint of vulcanization density and production efficiency.
- the heating method for vulcanization may be appropriately selected from the methods used for vulcanization of rubber, such as press heating, steam heating, oven heating, and hot air heating.
- the vulcanized rubber article of the present invention is manufactured by molding and vulcanizing each of the rubber products exemplified above into a predetermined shape by a conventional molding method.
- acrylonitrile units with nitrile rubber (iodine value 4, Mooney viscosity (ML 1 + 4 , 100 ° C) 85) 36.2% Atari mouth nitrile-butadiene copolymer rubber hydrogen Additives, ZEON Corporation, Zetpo 12000), organic sulfonate 1 (sodium dodecylbenzenesulfonate) or organic sulfonate 2 (sodium N-methyllauroyltaurine), and sodium carbonate As shown in the table below, Zinhua No.
- the obtained rubber composition is press-vulcanized at 170 ° C for 20 minutes to produce a vulcanized sheet having a thickness of 2 mm, subjected to a tensile test according to JIS K6301, and further subjected to an oven. After a heat aging test at 150 ° C or 170 ° C in air, a tensile test was performed to measure the change. Table 1 shows the results. table 1
- Comparative Example 1 in Table 1 shows the vulcanization properties of a rubber composition that does not contain a strong base, a salt of a strong base and a weak acid, or a weak acid salt / sulfonate, but the change in elongation due to heat load is large. Also, there is a large change in tensile strength due to high temperature heat load.
- Comparative Examples 2 and 3 are cases where lithium carbonate is contained as a weak acid salt.
- the change in elongation due to heat load is large, and the change in tensile strength is also large.
- Examples 1 to 5 in which sodium dodecylbenzenesulfonate is contained as the organic sulfonate, the change in elongation due to heat load is small and the change in tensile strength is also small.
- the rubber composition of the present invention By using the rubber composition of the present invention, it is possible to obtain a vulcanized rubber article having a small decrease in both tensile strength and elongation even in a heated air atmosphere.
- the vulcanized rubber article of the present invention is useful as an automobile part used in a heated air atmosphere, such as a ring, a seal, a packing, a gasket, a diaphragm, a hose, and a belt, utilizing its properties.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Description
Claims
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01912362A EP1270663A4 (en) | 2000-03-30 | 2001-03-14 | NITRILE RUBBER COMPOSITION AND VULCANIZED RUBBER ARTICLE |
| US10/239,839 US6835780B2 (en) | 2000-03-30 | 2001-03-14 | Nitrile rubber composition and vulcanized rubber article |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000094323A JP2001279021A (ja) | 2000-03-30 | 2000-03-30 | 加硫可能なニトリル系ゴム組成物および加硫ゴム物品 |
| JP2000-94323 | 2000-03-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2001074940A1 true WO2001074940A1 (en) | 2001-10-11 |
Family
ID=18609388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP2001/002022 Ceased WO2001074940A1 (en) | 2000-03-30 | 2001-03-14 | Nitrile rubber composition and vulcanized rubber article |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US6835780B2 (ja) |
| EP (1) | EP1270663A4 (ja) |
| JP (1) | JP2001279021A (ja) |
| WO (1) | WO2001074940A1 (ja) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6759457B2 (en) | 2002-02-21 | 2004-07-06 | Zeon Chemicals, L.P. | Unique compositions having utility in rubber applications |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003286351A (ja) | 2002-03-28 | 2003-10-10 | Tokai Rubber Ind Ltd | 耐熱ゴムの加硫接着方法 |
| JP3941102B2 (ja) | 2002-03-28 | 2007-07-04 | 東海ゴム工業株式会社 | 耐熱燃料ホース |
| JP5046224B2 (ja) * | 2007-02-20 | 2012-10-10 | 電気化学工業株式会社 | アクリルゴム組成物 |
| US8461378B2 (en) | 2010-09-10 | 2013-06-11 | E.I. Du Pont De Nemours And Company | Purification of fluoroalkanesulfonate salts |
| WO2012090941A1 (ja) * | 2010-12-27 | 2012-07-05 | 日本ゼオン株式会社 | ゴム組成物およびゴム架橋物 |
| KR101150982B1 (ko) | 2011-06-30 | 2012-06-08 | 주식회사 남익물산 | 시공성 및 난연성이 우수한 nbr 고무발포 단열재 |
| TWI667069B (zh) * | 2013-12-30 | 2019-08-01 | 德商艾朗希歐德意志有限公司 | 含硫化膦或硫化二膦之氫化腈橡膠 |
| CN104403148A (zh) * | 2014-12-09 | 2015-03-11 | 韦良富 | 汽车配件用橡胶密封圈 |
| KR101714266B1 (ko) * | 2015-12-03 | 2017-03-08 | 현대자동차주식회사 | 내한성이 향상된 오일씰 고무 조성물 및 이의 제조방법 |
| KR102267428B1 (ko) * | 2016-03-18 | 2021-06-18 | 니폰 제온 가부시키가이샤 | 니트릴 고무 조성물 및 고무 가교물 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5736136A (ja) * | 1980-08-14 | 1982-02-26 | Japan Synthetic Rubber Co Ltd | Kanagatanenchakugakairyosaretakureepuchogomusoseibutsu |
| US4965323A (en) * | 1983-05-17 | 1990-10-23 | Nippon Zeon Co., Ltd. | Method of vulcanizing rubber at pH 5 to 10 |
| JPH08120184A (ja) * | 1994-10-25 | 1996-05-14 | Japan Synthetic Rubber Co Ltd | 難燃用ベース樹脂組成物および難燃性樹脂組成物 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4452936A (en) * | 1982-05-17 | 1984-06-05 | The Goodyear Tire & Rubber Company | Oligomerized acids as scorch inhibitors for carboxylated rubbers |
| JP3622809B2 (ja) * | 1995-09-14 | 2005-02-23 | 日本ゼオン株式会社 | エチレン性不飽和カルボン酸金属塩含有エラストマー組成物および加硫エラストマーの成形方法 |
| EP0985704B1 (en) * | 1998-09-11 | 2003-11-05 | Mitsui Chemicals, Inc. | Nitrile resin composition |
-
2000
- 2000-03-30 JP JP2000094323A patent/JP2001279021A/ja active Pending
-
2001
- 2001-03-14 WO PCT/JP2001/002022 patent/WO2001074940A1/ja not_active Ceased
- 2001-03-14 US US10/239,839 patent/US6835780B2/en not_active Expired - Fee Related
- 2001-03-14 EP EP01912362A patent/EP1270663A4/en not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5736136A (ja) * | 1980-08-14 | 1982-02-26 | Japan Synthetic Rubber Co Ltd | Kanagatanenchakugakairyosaretakureepuchogomusoseibutsu |
| US4965323A (en) * | 1983-05-17 | 1990-10-23 | Nippon Zeon Co., Ltd. | Method of vulcanizing rubber at pH 5 to 10 |
| JPH08120184A (ja) * | 1994-10-25 | 1996-05-14 | Japan Synthetic Rubber Co Ltd | 難燃用ベース樹脂組成物および難燃性樹脂組成物 |
Non-Patent Citations (1)
| Title |
|---|
| See also references of EP1270663A4 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6759457B2 (en) | 2002-02-21 | 2004-07-06 | Zeon Chemicals, L.P. | Unique compositions having utility in rubber applications |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001279021A (ja) | 2001-10-10 |
| EP1270663A1 (en) | 2003-01-02 |
| US6835780B2 (en) | 2004-12-28 |
| EP1270663A4 (en) | 2005-01-26 |
| US20030236355A1 (en) | 2003-12-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6414068B2 (ja) | ニトリル共重合体ゴムおよびその製造方法 | |
| WO2015080130A1 (ja) | ニトリル基含有高飽和共重合体ゴム組成物およびゴム架橋物 | |
| JPH0370744B2 (ja) | ||
| JPWO2013015373A1 (ja) | ニトリル基含有高飽和共重合体ゴム組成物 | |
| JP5381985B2 (ja) | ニトリル基含有高飽和共重合体ゴム | |
| JP4221877B2 (ja) | ニトリル系ゴム組成物、架橋性ニトリル系ゴム組成物および架橋物 | |
| WO2017022598A1 (ja) | ニトリル基含有高飽和共重合体ゴム、架橋性ゴム組成物、およびゴム架橋物 | |
| WO2001074940A1 (en) | Nitrile rubber composition and vulcanized rubber article | |
| JP2023089198A (ja) | ニトリル基含有共重合体ゴムの製造方法 | |
| JP6614153B2 (ja) | 高飽和ニトリルゴム組成物およびゴム架橋物 | |
| JP2006335784A (ja) | 耐油耐候性ゴム組成物及びその成形品 | |
| JP2020084162A (ja) | 混合ゴムおよびその製造方法、架橋性ゴム組成物ならびにゴム架橋物 | |
| JP7200569B2 (ja) | ゴム混合液、ニトリル基含有共重合体ゴム組成物、架橋性ゴム組成物およびゴム架橋物 | |
| JP4075610B2 (ja) | アクリル酸エステル系共重合ゴム及びその製造方法、並びにそれを含むゴム組成物、耐油耐候性ゴム組成物及び耐油耐候性ゴム | |
| JP4019808B2 (ja) | 架橋性アクリルゴム組成物 | |
| JP4623280B2 (ja) | ゴム組成物、加硫性ゴム組成物および加硫物 | |
| JP2008231256A (ja) | 耐油耐候性ゴム組成物とその成形体 | |
| JPWO2004106429A1 (ja) | ゴム組成物およびその架橋成形物 | |
| JP2000290430A (ja) | 架橋性フッ素ゴム組成物、架橋物、ゴム積層体およびゴム積層体の製造方法 | |
| JP2015017168A (ja) | ホース用高飽和ニトリルゴム組成物およびホース | |
| JP2003246890A (ja) | ゴム組成物および加硫物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AK | Designated states |
Kind code of ref document: A1 Designated state(s): US |
|
| AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR |
|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
| DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
| WWE | Wipo information: entry into national phase |
Ref document number: 2001912362 Country of ref document: EP |
|
| WWP | Wipo information: published in national office |
Ref document number: 2001912362 Country of ref document: EP |
|
| WWE | Wipo information: entry into national phase |
Ref document number: 10239839 Country of ref document: US |