JPWO2015115521A1 - 架橋性ニトリルゴム組成物およびゴム架橋物 - Google Patents
架橋性ニトリルゴム組成物およびゴム架橋物 Download PDFInfo
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- JPWO2015115521A1 JPWO2015115521A1 JP2015560002A JP2015560002A JPWO2015115521A1 JP WO2015115521 A1 JPWO2015115521 A1 JP WO2015115521A1 JP 2015560002 A JP2015560002 A JP 2015560002A JP 2015560002 A JP2015560002 A JP 2015560002A JP WO2015115521 A1 JPWO2015115521 A1 JP WO2015115521A1
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- Prior art keywords
- nitrile rubber
- rubber composition
- parts
- compound
- carbon atoms
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 79
- 229920001971 elastomer Polymers 0.000 title claims description 55
- 239000005060 rubber Substances 0.000 title claims description 54
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 68
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
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- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 36
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 20
- 229920000768 polyamine Polymers 0.000 claims abstract description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 17
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 16
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 14
- 239000011630 iodine Substances 0.000 claims abstract description 14
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 claims abstract 3
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- 125000001424 substituent group Chemical group 0.000 claims description 16
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
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- 239000003505 polymerization initiator Substances 0.000 description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
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- 125000003277 amino group Chemical group 0.000 description 6
- UTOVMEACOLCUCK-PLNGDYQASA-N butyl maleate Chemical compound CCCCOC(=O)\C=C/C(O)=O UTOVMEACOLCUCK-PLNGDYQASA-N 0.000 description 6
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- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- XSQHUYDRSDBCHN-UHFFFAOYSA-N 2,3-dimethyl-2-propan-2-ylbutanenitrile Chemical compound CC(C)C(C)(C#N)C(C)C XSQHUYDRSDBCHN-UHFFFAOYSA-N 0.000 description 5
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 5
- 241001441571 Hiodontidae Species 0.000 description 5
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- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 5
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- 239000011976 maleic acid Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 238000007720 emulsion polymerization reaction Methods 0.000 description 4
- 239000001530 fumaric acid Substances 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 239000004816 latex Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 3
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- OKVDGQVSUDTBJI-UHFFFAOYSA-N 2-methoxy-1-methylimidazole Chemical compound COC1=NC=CN1C OKVDGQVSUDTBJI-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 3
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 229960000541 cetyl alcohol Drugs 0.000 description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 3
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- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 2
- HJSYENHCQNNLAS-UHFFFAOYSA-N 1,2,4-trimethyl-4,5-dihydroimidazole Chemical compound CC1CN(C)C(C)=N1 HJSYENHCQNNLAS-UHFFFAOYSA-N 0.000 description 2
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- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- KNBRWWCHBRQLNY-UHFFFAOYSA-N piperidine-1-carbothioylsulfanyl piperidine-1-carbodithioate Chemical compound C1CCCCN1C(=S)SSC(=S)N1CCCCC1 KNBRWWCHBRQLNY-UHFFFAOYSA-N 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- FZYCEURIEDTWNS-UHFFFAOYSA-N prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1.CC(=C)C1=CC=CC=C1 FZYCEURIEDTWNS-UHFFFAOYSA-N 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 238000007717 redox polymerization reaction Methods 0.000 description 1
- 238000010057 rubber processing Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000004964 sulfoalkyl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
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- 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
- C08K5/05—Alcohols; Metal alcoholates
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- 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
- C08K5/05—Alcohols; Metal alcoholates
- C08K5/053—Polyhydroxylic alcohols
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- 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
- C08K5/13—Phenols; Phenolates
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- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
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- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
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- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3445—Five-membered rings
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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
- C08L13/00—Compositions of rubbers containing carboxyl groups
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
- C08L9/02—Copolymers with acrylonitrile
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
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- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
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- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
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Abstract
Description
本発明の架橋性ニトリルゴム組成物において、前記化合物(C)が、炭素数1〜9の脂肪族アルコール(c1)であることが好ましい。
なお、炭素数1〜9の脂肪族アルコール(c1)としては、炭素数1〜9の多価脂肪族アルコールが好ましい。
また、本発明の架橋性ニトリルゴム組成物において、前記化合物(C)として、2種類以上の炭素数1〜9の多価脂肪族アルコールを含有することが好ましい。
本発明の架橋性ニトリルゴム組成物は、環状アミジン構造を有する塩基性架橋促進剤をさらに含有することが好ましい。
あるいは、本発明の架橋性ニトリルゴム組成物は、下記一般式(1)で表される塩基性架橋促進剤をさらに含有することが好ましい。
本発明の架橋性ニトリルゴム組成物は、ヨウ素価が120以下であるカルボキシル基含有ニトリルゴム(A)、ポリアミン架橋剤(B)、ならびに、炭素数1〜9の多価アルコール(c1)、ヒドロキシル基含有芳香族化合物(c2)および含窒素複素環式化合物(c3)から選択される少なくとも1種の化合物(C)を含有してなる。
まず、本発明で用いるヨウ素価が120以下であるカルボキシル基含有ニトリルゴム(A)について説明する。本発明で用いるヨウ素価が120以下であるカルボキシル基含有ニトリルゴム(A)(以下、単に「カルボキシル基含有ニトリルゴム(A)」ということがある。)は、α,β−エチレン性不飽和ニトリル単量体、カルボキシル基含有単量体、ならびに必要に応じて用いられる共役ジエン単量体およびα,β−エチレン性不飽和モノカルボン酸エステル単量体などを共重合することにより得られる、ヨウ素価が120以下のゴムである。
本発明の架橋性ニトリルゴム組成物は、ポリアミン架橋剤(B)を含有してなるものである。架橋剤として、ポリアミン架橋剤(B)を用いることにより、得られるゴム架橋物の耐圧縮永久歪み性が改善される。
本発明の架橋性ニトリルゴム組成物は、カルボキシル基含有ニトリルゴム(A)およびポリアミン架橋剤(B)に加えて、炭素数1〜9の脂肪族アルコール(c1)、ヒドロキシル基含有芳香族化合物(c2)および含窒素複素環式化合物(c3)から選択される少なくとも1種の化合物(C)を含有する。
また、本発明の架橋性ニトリルゴム組成物は、上述したカルボキシル基含有ニトリルゴム(A)、ポリアミン架橋剤(B)および化合物(C)に加えて、塩基性架橋促進剤を含有していることが好ましい。塩基性架橋促進剤をさらに含有させることにより、本発明の効果がより一層顕著になる。
また、R1およびR2は、置換基を有していないことが好ましい。
また、R3およびR4は、置換基を有していないことが好ましい。
グアニジン系塩基性架橋促進剤としては、テトラメチルグアニジン、テトラエチルグアニジン、ジフェニルグアニジン、1,3−ジ−オルト−トリルグアニジン、オルトトリルビグアニドなどが挙げられる。
アルデヒドアミン系塩基性架橋促進剤としては、n−ブチルアルデヒドアニリン、アセトアルデヒドアンモニアなどが挙げられる。
なお、混合機で混練する際に、カーボンブラック、シリカ、老化防止剤などの各種配合剤や、その他のゴムを同時に混合してもよい。
本発明のゴム架橋物は、上述した架橋性ニトリルゴム組成物を架橋してなるものである。
本発明のゴム架橋物は、本発明の架橋性ニトリルゴム組成物を用い、所望の形状に対応した成形機、たとえば、押出機、射出成形機、圧縮機、ロールなどにより成形を行い、加熱することにより架橋反応を行い、架橋物として形状を固定化することにより製造することができる。この場合においては、予め成形した後に架橋しても、成形と同時に架橋を行ってもよい。成形温度は、通常、10〜200℃、好ましくは25〜120℃である。架橋温度は、通常、100〜200℃、好ましくは130〜190℃であり、架橋時間は、通常、1分〜24時間、好ましくは2分〜1時間である。
これらのなかでも、本発明のゴム架橋物は、シール材、ガスケット、ベルトまたはホースとして好適に用いることができ、シール材として特に好適である。
カルボキシル基含有ニトリルゴムのヨウ素価は、JIS K 6235に準じて測定した。
2mm角のカルボキシル基含有ニトリルゴム0.2gに、2−ブタノン100mlを加えて16時間攪拌した後、エタノール20mlおよび水10mlを加え、攪拌しながら水酸化カリウムの0.02N含水エタノール溶液を用いて、室温でチモールフタレインを指示薬とする滴定により、ゴム100gに対するカルボキシル基のモル数として求めた(単位はephr)。
カルボキシル基含有ニトリルゴムを構成する各単量体単位の含有割合は、以下の方法により測定した。
すなわち、マレイン酸モノn−ブチル単位の含有割合は、上記「カルボキシル基含有量」の測定方法により、水素化後のカルボキシル基含有ニトリルゴム100gに対するカルボキシル基のモル数を求め、求めたモル数をマレイン酸モノn−ブチル単位の量に換算することにより算出した。
1,3−ブタジエン単位(水素化された部分も含む)の含有割合は、水素添加反応前のカルボキシル基含有ニトリルゴムのヨウ素価を上記方法で測定することにより算出した。
アクリロニトリル単位の含有割合は、JIS K6384に従い、ケルダール法により、水素化後のカルボキシル含有ニトリルゴム中の窒素含量を測定することにより算出した。
カルボキシル基含有ニトリルゴム、および架橋性ニトリルゴム組成物のムーニー粘度(ポリマームーニー、コンパウンドムーニー)は、JIS K6300に従って測定した(単位は〔ML1+4、100℃〕)。
架橋性ニトリルゴム組成物のムーニースコーチ時間t35を、JIS K6300に従って125℃で測定した。t35はムーニー粘度値最低値のVminからVが35上昇するまでの時間である。ムーニースコーチ時間t35の値が大きいほど、スコーチ安定性に優れる。
外径30mm、リング径3mmの金型を用いて、架橋性ニトリルゴム組成物を170℃で20分間、プレス圧5MPaで架橋した後、170℃で4時間二次架橋を行うことにより、O−リング状の試験片を得た。そして、得られたO−リング状の試験片を用いて、O−リング状の試験片を挟んだ二つの平面間の距離をリング厚み方向に25%圧縮した状態で150℃にて168時間保持する条件で、JIS K6262に従って、圧縮永久歪み(O−リング圧縮永久歪み)を測定した。この値が小さいほど、耐圧縮永久歪み性に優れる。
金属製ボトルに、イオン交換水180部、濃度10重量%のドデシルベンゼンスルホン酸ナトリウム水溶液25部、アクリロニトリル37部、マレイン酸モノn−ブチル6部、t−ドデシルメルカプタン(分子量調整剤)0.75部の順に仕込み、内部の気体を窒素で3回置換した後、1,3−ブタジエン57部を仕込んだ。金属製ボトルを5℃に保ち、クメンハイドロパーオキサイド(重合開始剤)0.1部、適量の還元剤、およびキレート剤を仕込み、金属製ボトルを回転させながら16時間重合反応した。その後、濃度10重量%のハイドロキノン水溶液(重合停止剤)0.1部を加えて重合反応を停止し、金属製ボトルの内容物をガラス製フラスコに移し、引き続いて、水温60℃のロータリーエバポレータを用いて減圧下で残留単量体を除去し、アクリロニトリル−ブタジエン−マレイン酸モノn−ブチル共重合体ゴムのラテックス(固形分濃度約30重量%)を得た。
得られたカルボキシル基含有高飽和ニトリルゴム(A−1)のヨウ素価は10、カルボキシル基含有量は3.2×10−2ephr、ポリマームーニー粘度(ML1+4、100℃)は45であった。また、カルボキシル基含有高飽和ニトリルゴム(A−1)の組成は、アクリロニトリル単位36重量%、ブタジエン単位(水素化されたものも含む)58.5重量%、およびマレイン酸モノn−ブチル単位5.5重量%であった。
バンバリーミキサを用いて、合成例1で得られたカルボキシル基含有高飽和ニトリルゴム(A−1)100部に、FEFカーボンブラック(商品名「シーストSO」、東海カーボン社製)40部、トリメリット酸トリ−2−エチルヘキシル(商品名「アデカサイザーC−8」、ADEKA社製、可塑剤)5部、4,4’−ジ−(α,α−ジメチルベンジル)ジフェニルアミン(商品名「ノクラックCD」、大内新興化学社製、老化防止剤)1.5部、ステアリン酸1部、ポリオキシエチレンアルキルエーテルリン酸エステル(商品名「フォスファノールRL210」、東邦化学工業社製、加工助剤)1部、2−プロパノール(炭素数1〜9の脂肪族アルコール(c1))2.5部を添加して、50℃で5分間混合した。次いで、得られた混合物を50℃のロールに移して、ヘキサメチレンジアミンカルバメート(商品名「Diak#1」、デュポンダウエラストマー社製、脂肪族多価アミン類に属するポリアミン架橋剤)2.4部、および1,8−ジアザビシクロ[5,4,0]−ウンデセン−7(DBU)(商品名「RHENOGRAN XLA−60(GE2014)」、RheinChemie社製、DBU60%(ジンクジアルキルジフォスフェイト塩になっている部分も含む)、塩基性架橋促進剤)4部を配合して、混練することにより、架橋性ニトリルゴム組成物を得た。
2−プロパノール2.5部の代わりに、1,2−プロパンジオール(炭素数1〜9の脂肪族アルコール(c1))2.5部を使用した以外は、実施例1と同様にして、架橋性ニトリルゴム組成物を調製し、同様に評価を行った。結果を表1に示す。
1,2−プロパンジオールの配合量を2.5部から5部に変更した以外は、実施例2と同様にして、架橋性ニトリルゴム組成物を調製し、同様に評価を行った。結果を表1に示す。
2−プロパノール2.5部の代わりに、グリセリン(炭素数1〜9の脂肪族アルコール(c1))2.5部を使用した以外は、実施例1と同様にして、架橋性ニトリルゴム組成物を調製し、同様に評価を行った。結果を表1に示す。
グリセリンの配合量を2.5部から5部に変更した以外は、実施例4と同様にして、架橋性ニトリルゴム組成物を調製し、同様に評価を行った。結果を表1に示す。
2−プロパノール2.5部の代わりに、エチレングリコール(炭素数1〜9の脂肪族アルコール(c1))2.5部を使用した以外は、実施例1と同様にして、架橋性ニトリルゴム組成物を調製し、同様に評価を行った。結果を表1に示す。
2−プロパノール2.5部の代わりに、ジエチレングリコール(炭素数1〜9の脂肪族アルコール(c1))2.5部を使用した以外は、実施例1と同様にして、架橋性ニトリルゴム組成物を調製し、同様に評価を行った。結果を表1に示す。
2−プロパノール2.5部の代わりに、3,5−ジ−t−ブチル−4−ヒドロキシトルエン(ヒドロキシル基含有芳香族化合物(c2))2.5部を使用した以外は、実施例1と同様にして、架橋性ニトリルゴム組成物を調製し、同様に評価を行った。結果を表1に示す。
2−プロパノール2.5部の代わりに、イミダゾール(含窒素複素環式化合物(c3))2.5部を使用した以外は、実施例1と同様にして、架橋性ニトリルゴム組成物を調製し、同様に評価を行った。結果を表1に示す。
2−プロパノール2.5部を配合しなかった以外は、実施例1と同様にして、架橋性ニトリルゴム組成物を調製し、同様に評価を行った。結果を表1に示す。
2−プロパノール2.5部の代わりに、n−ステアリルアルコール2.5部を使用した以外は、実施例1と同様にして、架橋性ニトリルゴム組成物を調製し、同様に評価を行った。結果を表1に示す。
2−プロパノール2.5部の代わりに、1,2−プロパンジオール2.5部およびグリセリン2.5部を使用した以外は、実施例1と同様にして、架橋性ニトリルゴム組成物を調製し、同様に評価を行った。結果を表2に示す。
1,2−プロパンジオールの配合量を2.5部から5部に、グリセリンの配合量を2.5部から5部にそれぞれ変更した以外は、実施例10と同様にして、架橋性ニトリルゴム組成物を調製し、同様に評価を行った。結果を表2に示す。
2−プロパノール2.5部の代わりに、1,2−プロパンジオール2.5部を使用するとともに、塩基性架橋促進剤として、1,8−ジアザビシクロ[5,4,0]−ウンデセン−7(DBU(商品名「RHENOGRAN XLA−60(GE2014)」、RheinChemie社製、DBU60%(ジンクジアルキルジフォスフェイト塩になっている部分も含む))4部の代わりに、エチレングリコールのジシクロヘキシルアミン塩と長鎖アルコールの混合物(商品名「ノックマスターEGS」、大内新興化学工業社製、エチレングリコールのジシクロヘキシルアミン塩80%並びに長鎖アルコール(1−テトラデカノール、1−ヘキサデカノール、1−オクタデカノール)20%からなるもの)4部を使用した以外は、実施例1と同様にして、架橋性ニトリルゴム組成物を調製し、同様に評価を行った。結果を表2に示す。
1,2−プロパンジオール2.5部の代わりに、グリセリン2.5部を使用した以外は、実施例12と同様にして、架橋性ニトリルゴム組成物を調製し、同様に評価を行った。結果を表2に示す。
1,2−プロパンジオール2.5部の代わりに、イミダゾール2.5部を使用した以外は、実施例12と同様にして、架橋性ニトリルゴム組成物を調製し、同様に評価を行った。結果を表2に示す。
化合物(C)として、1,2−プロパンジオール2.5部に加えて、グリセリン2.5部を併用した以外は、実施例12と同様にして、架橋性ニトリルゴム組成物を調製し、同様に評価を行った。結果を表2に示す。
1,2−プロパンジオールの配合量を2.5部から5部に、グリセリンの配合量を2.5部から5部にそれぞれ変更した以外は、実施例15と同様にして、架橋性ニトリルゴム組成物を調製し、同様に評価を行った。結果を表2に示す。
1,2−プロパンジオールの配合量を2.5部から1.5部に、グリセリンの配合量を2.5部から3.5部にそれぞれ変更した以外は、実施例15と同様にして、架橋性ニトリルゴム組成物を調製し、同様に評価を行った。結果を表3に示す。
化合物(C)として、グリセリン2.5部に加えて、ジエチレングリコール2.5部を併用した以外は、実施例13と同様にして、架橋性ニトリルゴム組成物を調製し、同様に評価を行った。結果を表3に示す。
ヘキサメチレンジアミンカルバメートの配合量を2.4部から2.8部に変更した以外は、実施例4と同様にして、架橋性ニトリルゴム組成物を調製し、同様に評価を行った。結果を表3に示す。
2−プロパノール2.5部の代わりに、1−ヘキサデカノール2.5部を使用した以外は、実施例1と同様にして、架橋性ニトリルゴム組成物を調製し、同様に評価を行った。結果を表3に示す。
また、実施例1〜19のなかでも、炭素数1〜9の多価脂肪族アルコールを用いた実施例2〜7,10〜19は、スコーチ安定性に特に優れるものであり、特に良好な結果であった。
また、化合物(C)の代わりに、n−ステアリルアルコール(炭素数18の脂肪族アルコール)や1−ヘキサデカノール(炭素数16の脂肪族アルコール)を使用した場合には、得られる架橋性ニトリルゴム組成物は、スコーチ時間が短く、スコーチ安定性に劣る結果となった(比較例2,3)。
Claims (8)
- ヨウ素価が120以下であるカルボキシル基含有ニトリルゴム(A)、ポリアミン架橋剤(B)、ならびに、炭素数1〜9の脂肪族アルコール(c1)、ヒドロキシル基含有芳香族化合物(c2)および含窒素複素環式化合物(c3)から選択される少なくとも1種の化合物(C)を含有してなる架橋性ニトリルゴム組成物。
- 前記化合物(C)が、炭素数1〜9の脂肪族アルコール(c1)である請求項1に記載の架橋性ニトリルゴム組成物。
- 前記炭素数1〜9の脂肪族アルコール(c1)が、炭素数1〜9の多価脂肪族アルコールである請求項2に記載の架橋性ニトリルゴム組成物。
- 前記化合物(C)として、2種類以上の炭素数1〜9の多価脂肪族アルコールを含有する請求項1に記載の架橋性ニトリルゴム組成物。
- 環状アミジン構造を有する塩基性架橋促進剤をさらに含有する請求項1〜4のいずれかに記載の架橋性ニトリルゴム組成物。
- 請求項1〜6のいずれか1項に記載の架橋性ニトリルゴム組成物を架橋してなるゴム架橋物。
- シール材である請求項7に記載のゴム架橋物。
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