WO1997016484A1 - COMPOSITION CAOUTCHOUTEUSE COMPRENANT UN CAOUTCHOUC COPOLYMERE DE NITRILE HAUTEMENT SATURE ET UN CAOUTCHOUC COPOLYMERE D'ETHYLENE-α-OLEFINE - Google Patents

COMPOSITION CAOUTCHOUTEUSE COMPRENANT UN CAOUTCHOUC COPOLYMERE DE NITRILE HAUTEMENT SATURE ET UN CAOUTCHOUC COPOLYMERE D'ETHYLENE-α-OLEFINE Download PDF

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Publication number
WO1997016484A1
WO1997016484A1 PCT/JP1996/002847 JP9602847W WO9716484A1 WO 1997016484 A1 WO1997016484 A1 WO 1997016484A1 JP 9602847 W JP9602847 W JP 9602847W WO 9716484 A1 WO9716484 A1 WO 9716484A1
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WIPO (PCT)
Prior art keywords
ethylene
copolymer rubber
rubber
rubber composition
olefin
Prior art date
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PCT/JP1996/002847
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English (en)
Japanese (ja)
Inventor
Yoshiaki Aimura
Hiroko Ohnishi
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.
Publication of WO1997016484A1 publication Critical patent/WO1997016484A1/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
    • C08L15/00—Compositions of rubber derivatives
    • C08L15/005—Hydrogenated nitrile rubber
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/14—Peroxides

Definitions

  • Rubber composition comprising nitrile group-containing highly saturated copolymer rubber and ethylene- ⁇ -olefin copolymer rubber
  • the present invention relates to a 'vulcanizable rubber composition
  • a 'vulcanizable rubber composition comprising a nitrile group-containing highly saturated copolymer rubber and an ethylene-based saturated copolymer rubber.
  • Some rubber compositions comprising a nitrile group-containing highly saturated copolymer rubber and an ethylene-based saturated copolymer rubber are known.
  • Japanese Unexamined Patent Publication (Kokai) No. Sho 61-2833639 discloses that the processability of ethylene-propylene rubber can be improved by blending hydrogenated acrylonitrile-butadiene copolymer rubber at a maximum of about 30% by weight. It is reported to be improved.
  • Japanese Unexamined Patent Publication (Kokai) No. 61-43032 discloses a nitrile group-containing highly saturated copolymer obtained by hydrogenating a nitrile group-containing elastomer obtained by copolymerizing acrylic acid, alkyl acrylate and the like. It has been reported that a homogeneous co-vulcanizate obtained by vulcanizing a mixture of rubber and an ethylene-propylene copolymer rubber with an organic peroxide vulcanizing agent can be obtained.
  • Partial hydrogenation obtained by hydrogenating a gen-based copolymer rubber A mixture of an unsaturated nitrile-one conjugated gen-based copolymer rubber and an ethylene-propylene-non-conjugated terpolymer rubber is accelerated by a thiram system It was reported that vulcanization using a sulfur-based vulcanizing agent containing a dithiol-balvate-based vulcanizing agent can provide rubber materials with excellent oil resistance and the like.
  • An object of the present invention is to provide a rubber material having excellent balance such as oil resistance, heat resistance, weather resistance, and cold resistance and improved compression set.
  • a nitrile group-containing highly saturated copolymer rubber obtained by hydrogenating a conjugated gen moiety of an unsaturated nitrile conjugated gen-unsaturated dicarboxylic acid ester copolymer and an ethylene- ⁇ -olefin olefin
  • a vulcanizable rubber composition comprising a copolymer rubber and an organic peroxide-based vulcanizing agent.
  • the nitrile group-containing highly saturated copolymer rubber used in the present invention is obtained by hydrogenating the conjugated part of an unsaturated nitrile-conjugated di-unsaturated dicarboxylic acid ester copolymer. It has a knee viscosity of 15 to 200, preferably 30 to 100, and an iodine value of 80 or less, preferably 40 or less. If the Mooney viscosity is less than 15, only low strength molded products can be obtained. If the Mooney viscosity exceeds 200, the viscosity will increase and molding will be difficult.
  • the lower limit for the iodine value is usually at least 1. If the iodine value is too low, vulcanization becomes difficult. If the iodine value is excessively high, heat resistance and weather resistance will decrease.
  • the unsaturated nitrile examples include acrylonitrile, methacrylonitrile, ⁇ -chloroacrylonitrile and the like. Of these, acrylonitrile is preferred.
  • the content of bound unsaturated nitrile units in the copolymer is from 10 to 40% by weight, and preferably from 15 to 30% by weight, based on the weight of the copolymer.
  • conjugated diene examples include 1,3-butadiene, 2,3-dimethylbutane, isoprene, and 1,3-benzene. Among them, 1,3-butadiene is preferred.
  • the content of bound conjugated gen units in the copolymer is usually from 10 to 70% by weight, preferably from 30 to 60% by weight, based on the weight of the copolymer. Oh "O o
  • unsaturated dicarboxylic acid esters include monomethyl maleate, monoethyl maleate, monobutyrate maleate, mono-n-butyl maleate, monoisobutyl maleate, mono-n-maleic acid n-bentyl, and monomaleic acid.
  • N-Hexyl mono-2-maleylhexyl maleate, monomethyl fumarate, monoethyl fumarate, monobutamate fumarate, mono-n-butyl fumarate, monoisobutyl fumarate, mono-n-fumarate n-bentyl, fumarate Mono-n-hexyl acid, mono-2-ethyl fumarate, monomethyl itaconate, monoethyl itaconate, monopropyl itaconate, mono-n-butyl itaconate, mono-isobutyl itaconate, mono-n-bentyl itaconate, itacon Acid mono-n-hexyl, itako Mono-2-ethyl citrate, monomethyl citraconic acid, monoethyl citraconic acid, monobutyric acid citraconic acid, mono-n-butyl citraconic acid, monoisobutyl citraconic acid, mono-citraconic acid n-ben
  • unsaturated dicarboxylic acid ester monomers those having 4 to 6 carbon atoms
  • An ester of a saturated dicarboxylic acid which is an unsaturated dicarboxylic acid dialkyl ester having an alkyl group having 1 to 5 carbon atoms, preferably 2 to 4 carbon atoms, is suitable.
  • the content of the unsaturated dicarboxylic acid ester monomer unit is usually 1 to 80% by weight, preferably 15 to 60% by weight, more preferably 20 to 40% by weight based on the weight of the copolymer. Range.
  • the oil resistance, heat resistance, weather resistance, and cold resistance of the nitrile group-containing highly saturated copolymer rubber can be improved.
  • the balance of properties can be improved. If the amount of the unsaturated dicarboxylic acid ester is too small, a nitrile group-containing highly saturated copolymer rubber having a good balance of oil resistance, heat resistance, weather resistance and cold resistance cannot be obtained. Conversely, if the amount is too large, the oil resistance decreases.
  • copolymerizable monomers can be used in addition to the above-mentioned monomers as long as the effects obtained by the present invention are not impaired.
  • copolymerizable monomers include vinyl monomers such as styrene, ⁇ -methylstyrene and vinyl pyridine; non-conjugated monomers such as vinyl norbornene, dicyclopentane and 1,4-hexadiene.
  • Fluoroalkyl such as fluoroethyl vinyl ether, fluorovyl vinyl ether, trifluoromethyl vinyl ether, trifluoroethyl vinyl ether, bar fluororubil vinyl ether, and fluoroxyhexyl vinyl ether
  • Fluorine-containing vinyl monomers such as vinyl ether, ⁇ - or ⁇ -trifluoromethylstyrene, vinyl pentafluorobenzoate, difluoroethylene, tetrafluoroethylene; and polyethylene glycol (meth) acrylate, polypropylene glycolMeth) Akuri rate, epoxy (meth) Akuri rate, such as urethane (meth) Akurireto the like.
  • Methoxymethyl acrylate, methoxyl acrylate, ethoxyxyl acrylate, butoxyshethyl acrylate, ethoxypropyl acrylate, methoxyxyl acrylate, ethoxybutoxy acrylate Acrylates having an alkoxyalkyl group having about 2 to 12 carbon atoms, such as acrylates;
  • 2-acrylates having a hydroxyalkyl group such as hydroxyethyl acrylate and hydroxybile acrylate; dimethylaminomethyl acrylate, getylaminoethyl acrylate; 3— Unsaturated monocarboxylic acid ester monomers such as (ethylethylamino) 12—hydroxyl mouth acrylate and 2,3-bis (difluoroamino) broacrylate
  • the amount of the copolymerizable monomer used is usually 10% by weight or less, preferably 5% by weight or less, based on the total weight of all monomers.
  • the method of hydrogenating the unsaturated nitrile conjugated gen-unsaturated dicarboxylic acid ester copolymer is not particularly limited, and the hydrogenation can be performed according to a conventional method.
  • the catalyst used in the hydrogenation include palladium Z silica and a palladium complex (JP-A-3-252405).
  • JP-A-62-125858, JP-A-6-42939, JP-A-1-45402, JP-A-145504 And rhodium or ruthenium compounds as described in JP-A No. 1-44504, JP-A No. 1-45405 and the like can also be used.
  • the nitrile group-containing highly saturated copolymer rubber used in the present invention can also be obtained by a method of directly hydrogenating a latex of an unsaturated nitrile-conjugated di-unsaturated carboxylic acid ester copolymer.
  • the method for direct hydrogenation include a method using a palladium catalyst (for example, JP-A-2-178305), a method using a rhodium-based catalyst (for example, JP-A-59-1111). No. 5303, JP-A-56-133209, U.S. Pat. No. 3,988,208), and a method using a ruthenium-based catalyst (for example, No.
  • the nitrile group-containing unsaturated copolymer is dissolved or swelled as described in JP-A-2-178305.
  • the organic solvent to be added is added to the copolymer latex. According to this method, the nitrile group-containing unsaturated copolymer in the copolymer latex swells with the organic solvent, and the hydrogenation catalyst can be easily approached to the double bond in the copolymer. However, the hydrogenation reaction can be efficiently performed while maintaining the aqueous emulsion state.
  • the palladium compound include, for example, formic acid, acetic acid, propionic acid, Palladium salts of carboxylic acids such as lauric acid, succinic acid, stearic acid, oleic acid, phthalic acid, and benzoic acid; palladium chloride, dichloro (cyclooctadiene) palladium, dichloro (norbornadiene) palladium, dichloro (benzonitrile) Chlorinated products of palladium, such as radium, dichlorobis (triphenylphosphine) palladium, ammonium tetrachloride palladium (II) acid, and hexachloropalladium (IV) ammonium palladium; palladium bromide; palladium iodide Complex salts of inorganic compounds such as potassium, valadium sulfate, dihydrate; potassium tetracyanopalladium (II) acid salt, trihydrate; and the like
  • the ethylene- ⁇ -olefin copolymer rubber used in the present invention is a copolymer of ethylene and ⁇ -olefin or a copolymer of ethylene, ⁇ -olefin and non-conjugated gen.
  • the copolymer rubber is usually a low-crystalline or amorphous elastomer having a crystallinity of 20% or less, more preferably 10% or less, or a mixture thereof.
  • ethylene-propylene-non-conjugated gen terpolymer rubber is preferred.
  • non-conjugated diene dicyclopentane, 1,4-hexadiene, cyclooctadiene, methylidene norbornene, 5-ethylidene-2-norbornene and the like are used. Of these, dicyclopentadiene And 5-ethylidene-12-norbornene are preferred.
  • the Mooney viscosity [ ⁇ 1 + 4 (100 ° C.)] of the ethylene- ⁇ -olefin refin-based copolymer rubber is usually from 10 to 180, preferably from 40 to: L 4 0, and Its iodine unsaturation is preferably 20 or less.
  • the ratio of ethylene unit to olefin unit is 50 ⁇ 50 to 90 ⁇ 10, preferably 60 40 to 84/16 (molar ratio).
  • (ethylene + ⁇ -olefin) units Non-co-functional gen units are usually 98 ⁇ 2-90 ⁇ 10, preferably 97 ⁇ 3-94 ⁇ 6 (molar ratio) .
  • the mixing ratio of the nitrile group-containing highly saturated copolymer rubber and the ethylene- ⁇ -olefin copolymer rubber is usually 95 to 20% by weight, preferably the nitrile group-containing highly saturated copolymer rubber. 70 to 50% by weight, and ethylene to ⁇ -olefin copolymer rubber 5 to 80% by weight, preferably 30 to 50% by weight. If the relative proportion of the nitrile group-containing highly saturated copolymer rubber is excessively large, the weather resistance is reduced, and if the relative proportion of the ethylene- ⁇ -olefin copolymer rubber is excessively large, the oil resistance is reduced. Decrease.
  • the method for blending the nitrile group-containing highly saturated copolymer rubber and the ethylene- ⁇ -olefin copolymer rubber is not particularly limited, but usually, the nitrile group-containing highly saturated copolymer rubber and ethylene- Dry blending method in which ⁇ -blended copolymer rubber is mixed at a high temperature using a Banbury mixer, etc., or nitrile-containing highly saturated copolymer rubber and ethylene- ⁇ -blended copolymer A latex coprecipitation method is used in which the combined rubber is mixed in a latex state, coagulated and dried, and then heat-treated using an extruder or Banbury mixer.
  • the organic peroxide-based vulcanizing agent used in the present invention is not particularly limited as long as it is one used in ordinary peroxide vulcanization of rubber.
  • Examples include dicumyl peroxide, g-tert-butyl peroxide, t-butylcumyl peroxide, benzoyl peroxide, 2,5-dimethyl-1,2,5-dihexylhexyl Examples include 1,3,2,5-dimethyl-2,5-di (benzoylpropoxy) hexine, a, a'-bis (t-butylperoxy-1m-ibbguchi) benzene and the like. Above all, G-t-butyl alcohol Is preferred. These organic peroxides are used in an amount of 0.1 to 15 parts by weight based on 100 parts by weight of the copolymer rubber.
  • examples of the crosslinking aid include unsaturated compounds used in ordinary organic peroxide vulcanization. Specific examples thereof include ethylene glycol dimethacrylate, trimethylolpropane remethacrylate, polyfunctional methyl methacrylate monomer, N, ⁇ '-m-phenylenediimide, triaryl isocyanate Nurate and the like. Of these, triallyl isocyanurate is preferred from the viewpoint of vulcanization properties. These addition amounts are in the range of 0.1 to 15 parts by weight based on 100 parts by weight of the copolymer rubber.
  • an organic peroxide-based vulcanizing agent as the vulcanizing agent.
  • a sulfur-based vulcanizing agent other than the organic peroxide-based vulcanizing agent is used, for example, it becomes difficult to obtain a rubber material having particularly excellent compression set resistance.
  • the vulcanizable rubber composition of the present invention may further contain other compounding agents used in the rubber field, such as reinforcing agents (various carbon black, silica, talc, etc.), agent (calcium carbonate, clay, etc.), processing aids, processing oils (including plasticizer), antioxidants, the vulcanizable rubber composition of c it should be noted that the present invention can be blended with ozone ⁇ inhibitor, If necessary, use a combination of other rubbers such as acrylic rubber, fluorine rubber, acrylonitrile-butadiene rubber, styrene-butadiene copolymer rubber, natural rubber, polyisobrene rubber, and ethylene-vinyl acetate copolymer resin. can do.
  • other compounding agents used in the rubber field such as reinforcing agents (various carbon black, silica, talc, etc.), agent (calcium carbonate, clay, etc.), processing aids, processing oils (including plasticizer), antioxidants, the vulcanizable
  • the method for producing the vulcanizable rubber composition of the present invention is not particularly limited, but usually, the raw material copolymer rubber and the vulcanization system and other compounding agents are mixed by a mixer such as a mouth or a Banbury mixer. To produce the rubber composition.
  • the characteristics of the rubber composition and the raw material components were measured as follows.
  • JISK 6301 prepared according to the formulation shown in Table 1.
  • a 2 mm thick sheet obtained by vulcanizing the unvulcanized rubber composition at 170 ° C for 30 minutes was punched out using a No. 3 type bender to prepare a test piece, and the tensile strength ( Unit: kgf Z cm2), 100% tensile stress (unit: kgf / cm2) and elongation (unit:%) were measured.
  • the hardness was measured using a JIS spring type A hardness tester. Further, the compression set was measured in accordance with JIS K6301 when the sample was kept at 150 at 77 hours and when it was kept at 120 at 8 hours (unit:%).
  • the rubber test piece was immersed in lubricating oil No. 3 (150, 72 hours), and the volume change rate (unit:%) was measured.
  • the ozone concentration is 50 ppm and the temperature is 40. After elongating statically at 20% in C, and then allowed to stand for 12, 24, 48 and 72 hours, the state of crack generation was observed. In Tables 7 to 11, “NC” indicates that no cracks were found.
  • a nitrile group-containing highly saturated copolymer rubber (HN BR 1-4, 8-11) having an unsaturated dicarboxylic acid ester unit shown in Tables 1-2 and ethylene-like one-year-old olefin copolymer rubber (EP DM1, 2) were mixed in the proportions (% by weight) shown in Tables 3 and 4, and an evaluation test was performed on a vulcanizable rubber composition containing an organic peroxide vulcanizing agent. Show results? ⁇ 10.
  • HN BRs 7 and 14 are highly saturated copolymer rubbers containing no unsaturated carboxylic acid ester units, obtained by hydrogenating a binary copolymer of acrylonitrile and bushugen. Evaluation tests were performed on these in the same manner as described above (Comparative Examples 3, 4, 6, 9, 10, and 12), and the results are shown in Tables 8 and 10.
  • the formulation of the vulcanizable rubber composition (Examples 1 to 6, Comparative Examples 1 to 12) is as follows.
  • Copolymer rubber mixture 00 parts FT carbon black 60 parts
  • 1,3-Bis (tert-butylperoxyisopropyl) benzene 8 parts The following ethylene- ⁇ -olefin copolymer rubber was used.
  • EP Ml Ethylene-propylene dicycloventene copolymer
  • Ethylene Z-brovilene Z-dicycloben-yen 55/40/5 (molar ratio) Muney viscosity 80
  • EPDM2 Ethylene-propylene-ethylidene norbornene copolymer
  • Zinc salt of mercaptobenzimidazole 1.5 parts Zinc flower 5 parts Stearate 1 part Sulfur 0.5 part 20 Tetramethylthiuram disulfide 1.5 parts
  • the vulcanizate obtained by vulcanizing the rubber composition of the present invention has lower cold resistance and oil resistance than the copolymer rubber having an unsaturated monocarboxylic acid ester unit. It is understood that the heat resistance and the compression set are improved while the weather resistance is well balanced.
  • the vulcanized product obtained by vulcanizing the rubber composition of the present invention has an excellent balance of cold resistance, oil resistance, and weather resistance, and has improved heat resistance and compression set. It is effective when used for rubber parts that require cold and oil resistance.
  • the vulcanizable rubber composition of the present invention can be used for various sealing rubber products such as O-rings, packings, gaskets, etc .; various belts such as conveyor belts, V-belts, timing belts; BOP (blow-out preventer), bladders, etc .; various cushioning materials, vibration-proof materials, etc .; can be widely used in the production of various hoses such as oil hoses, marine hoses, risers, flow lines, etc. .

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  • 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)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Cette invention concerne une composition caoutchouteuse comprenant les éléments suivants: un caoutchouc copolymère de nitrile hautement saturé obtenu par l'hydrogénation de fragments diènes conjugués d'un copolymère non saturé d'ester dicarboxylique non saturé en diène et conjugué à un nitrile (de préférence, un ester de dialkyle d'un acide dicarboxylique non saturé); un caoutchouc copolymère d'éthylène-α-oléfine (de préférence, un caoutchouc copolymère de diène non conjugué à un éthylène-α-oléfine); et, enfin, un agent de vulcanisation à base de peroxyde organique. Le produit de vulcanisation obtenu à l'aide de cette composition, possède des qualités excellentes et bien équilibrées de résistance au froid, à l'huile et aux intempéries, ainsi qu'une meilleure résistance thermique et une meilleure rémanence à la compression. Ce produit est utile dans la fabrication de pièces faites de caoutchouc qui entrent en contact avec des huiles ou des gaz divers, et qui doivent résister au froid et aux huiles.
PCT/JP1996/002847 1995-10-31 1996-10-01 COMPOSITION CAOUTCHOUTEUSE COMPRENANT UN CAOUTCHOUC COPOLYMERE DE NITRILE HAUTEMENT SATURE ET UN CAOUTCHOUC COPOLYMERE D'ETHYLENE-α-OLEFINE WO1997016484A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP7/306463 1995-10-31
JP30646395A JP3620552B2 (ja) 1995-10-31 1995-10-31 ニトリル基含有高飽和共重合体ゴムとエチレン−α−オレフイン系共重合体ゴムとからなるゴム組成物

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JP4062828B2 (ja) * 1999-08-20 2008-03-19 日本ゼオン株式会社 架橋性ゴム組成物および架橋物
JP4792708B2 (ja) * 2004-04-28 2011-10-12 横浜ゴム株式会社 コンベヤベルト用ゴム組成物およびコンベヤベルト
JP2006144878A (ja) * 2004-11-18 2006-06-08 Yokohama Rubber Co Ltd:The マリンホース
WO2006057392A1 (fr) * 2004-11-29 2006-06-01 Zeon Corporation Composition pour formage par immersion et article moulé formé par immersion

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6140342A (ja) * 1983-12-14 1986-02-26 バイエル・アクチエンゲゼルシヤフト 重合体混合物
JPH0686554B2 (ja) * 1985-06-11 1994-11-02 エヌオーケー株式会社 エチレン‐プロピレン系ゴム組成物

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6140342A (ja) * 1983-12-14 1986-02-26 バイエル・アクチエンゲゼルシヤフト 重合体混合物
JPH0686554B2 (ja) * 1985-06-11 1994-11-02 エヌオーケー株式会社 エチレン‐プロピレン系ゴム組成物

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JP3620552B2 (ja) 2005-02-16

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