JP2023125069A - Nitrile rubber composition and rubber crosslinked product - Google Patents
Nitrile rubber composition and rubber crosslinked product Download PDFInfo
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- JP2023125069A JP2023125069A JP2022028991A JP2022028991A JP2023125069A JP 2023125069 A JP2023125069 A JP 2023125069A JP 2022028991 A JP2022028991 A JP 2022028991A JP 2022028991 A JP2022028991 A JP 2022028991A JP 2023125069 A JP2023125069 A JP 2023125069A
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- Prior art keywords
- nitrile rubber
- rubber
- oil
- extended
- plasticizer
- 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.)
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- 229920000459 Nitrile rubber Polymers 0.000 title claims abstract description 171
- 229920001971 elastomer Polymers 0.000 title claims abstract description 82
- 239000005060 rubber Substances 0.000 title claims abstract description 82
- 239000000203 mixture Substances 0.000 title claims abstract description 75
- 239000004014 plasticizer Substances 0.000 claims abstract description 71
- 238000013329 compounding Methods 0.000 claims abstract description 32
- 239000000945 filler Substances 0.000 claims abstract description 15
- 238000004132 cross linking Methods 0.000 claims description 33
- -1 adipic acid ether ester Chemical class 0.000 claims description 31
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 20
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 17
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 11
- WNLRTRBMVRJNCN-UHFFFAOYSA-N hexanedioic acid Natural products OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 10
- 239000001361 adipic acid Substances 0.000 claims description 8
- 235000011037 adipic acid Nutrition 0.000 claims description 8
- 238000012360 testing method Methods 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 4
- 239000000654 additive Substances 0.000 abstract description 9
- 230000000996 additive effect Effects 0.000 abstract description 8
- 239000000178 monomer Substances 0.000 description 39
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
- 239000003431 cross linking reagent Substances 0.000 description 26
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 229910052717 sulfur Inorganic materials 0.000 description 13
- 239000011593 sulfur Substances 0.000 description 13
- 239000003921 oil Substances 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 12
- 150000001993 dienes Chemical class 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 239000011256 inorganic filler Substances 0.000 description 10
- 229910003475 inorganic filler Inorganic materials 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 150000002825 nitriles Chemical class 0.000 description 9
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- 229940018560 citraconate Drugs 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 239000004927 clay Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 238000004073 vulcanization Methods 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000006229 carbon black Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 6
- 238000000465 moulding Methods 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 5
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000004898 kneading Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 230000003712 anti-aging effect Effects 0.000 description 4
- 239000002826 coolant Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000001530 fumaric acid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 4
- 229960002447 thiram Drugs 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 229910052570 clay Inorganic materials 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 3
- 150000001451 organic peroxides Chemical class 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- 235000014692 zinc oxide Nutrition 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 2
- CQDDDLREQHQBRR-UHFFFAOYSA-N 1-cyanoethyl prop-2-enoate Chemical compound N#CC(C)OC(=O)C=C CQDDDLREQHQBRR-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000000378 calcium silicate Substances 0.000 description 2
- 229910052918 calcium silicate Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229940018557 citraconic acid Drugs 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 description 2
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
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- AYAUWVRAUCDBFR-ARJAWSKDSA-N (z)-4-oxo-4-propoxybut-2-enoic acid Chemical compound CCCOC(=O)\C=C/C(O)=O AYAUWVRAUCDBFR-ARJAWSKDSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- GWYSWOQRJGLJPA-UHFFFAOYSA-N 1,1,2,2-tetrafluoropropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(F)(F)C(C)(F)F GWYSWOQRJGLJPA-UHFFFAOYSA-N 0.000 description 1
- WFLOTYSKFUPZQB-UHFFFAOYSA-N 1,2-difluoroethene Chemical group FC=CF WFLOTYSKFUPZQB-UHFFFAOYSA-N 0.000 description 1
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- UBRWPVTUQDJKCC-UHFFFAOYSA-N 1,3-bis(2-tert-butylperoxypropan-2-yl)benzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC(C(C)(C)OOC(C)(C)C)=C1 UBRWPVTUQDJKCC-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- GWQOYRSARAWVTC-UHFFFAOYSA-N 1,4-bis(2-tert-butylperoxypropan-2-yl)benzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=C(C(C)(C)OOC(C)(C)C)C=C1 GWQOYRSARAWVTC-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- IPJGAEWUPXWFPL-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(N2C(C=CC2=O)=O)=C1 IPJGAEWUPXWFPL-UHFFFAOYSA-N 0.000 description 1
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- HKLPOBRVSAUJSG-UHFFFAOYSA-N n-(4-anilinophenyl)prop-2-enamide Chemical compound C1=CC(NC(=O)C=C)=CC=C1NC1=CC=CC=C1 HKLPOBRVSAUJSG-UHFFFAOYSA-N 0.000 description 1
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- 229920003052 natural elastomer Polymers 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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- 229910052625 palygorskite Inorganic materials 0.000 description 1
- QUPCNWFFTANZPX-UHFFFAOYSA-M paramenthane hydroperoxide Chemical compound [O-]O.CC(C)C1CCC(C)CC1 QUPCNWFFTANZPX-UHFFFAOYSA-M 0.000 description 1
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
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- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
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- 238000011160 research Methods 0.000 description 1
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- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
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- 238000009628 steelmaking Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- 229940052367 sulfur,colloidal Drugs 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 239000006234 thermal black Substances 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- XKMZOFXGLBYJLS-UHFFFAOYSA-L zinc;prop-2-enoate Chemical compound [Zn+2].[O-]C(=O)C=C.[O-]C(=O)C=C XKMZOFXGLBYJLS-UHFFFAOYSA-L 0.000 description 1
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- Processes Of Treating Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
本発明は、ニトリルゴム組成物に関し、さらに詳しくは、低硬度で、かつ引張強度に優れたゴム架橋物を与えることのできるニトリルゴム組成物、および、このようなニトリルゴム組成物を用いて得られるゴム架橋物に関する。 The present invention relates to a nitrile rubber composition, and more specifically, a nitrile rubber composition that can provide a rubber crosslinked product with low hardness and excellent tensile strength, and a nitrile rubber composition that can be obtained using such a nitrile rubber composition. The present invention relates to crosslinked rubber products.
従来から、ニトリルゴム（アクリロニトリル－ブタジエン共重合ゴム）は、耐油性に優れるゴムとして知られており、その加硫物は主にホース、ベルト、ガスケット、パッキン、シール、ロールなど産業用・自動車用の各種油類まわりのゴム製品の材料として用いられている。 Nitrile rubber (acrylonitrile-butadiene copolymer rubber) has traditionally been known as a rubber with excellent oil resistance, and its vulcanized products are mainly used for industrial and automotive applications such as hoses, belts, gaskets, packings, seals, and rolls. It is used as a material for rubber products around various oils.
このようなニトリルゴムの組成物として、たとえば、特許文献１には、アクリロニトリル－ブタジエンゴムと、シリカと、エーテルエステル系可塑剤と、架橋剤とからなるニトリルゴム組成物が開示されている。特許文献１に記載のニトリルゴム組成物によれば、耐寒性と耐熱性に優れ、圧縮永久歪みが小さく、かつ、耐油性に優れたゴム架橋物が得られている。 As such a nitrile rubber composition, for example, Patent Document 1 discloses a nitrile rubber composition comprising acrylonitrile-butadiene rubber, silica, an ether ester plasticizer, and a crosslinking agent. According to the nitrile rubber composition described in Patent Document 1, a crosslinked rubber product having excellent cold resistance and heat resistance, low compression set, and excellent oil resistance is obtained.
ここで、ニトリルゴムのゴム架橋物には、その用途に応じて、耐油性に加え、低硬度であることが求められる。しかしながら、特許文献１に記載のニトリルゴム組成物では、ゴム架橋物の低硬度化を図るために可塑剤の含有量を増やした場合に、得られるゴム架橋物の引張強度が低下するおそれがあるという問題があった。 Here, the rubber crosslinked product of nitrile rubber is required to have low hardness in addition to oil resistance depending on its use. However, in the nitrile rubber composition described in Patent Document 1, when the content of the plasticizer is increased in order to lower the hardness of the rubber crosslinked product, the tensile strength of the obtained rubber crosslinked product may decrease. There was a problem.
本発明は、このような実状に鑑みてなされたものであり、低硬度で、かつ引張強度に優れたゴム架橋物を与えることのできるニトリルゴム組成物、および、このようなニトリルゴム組成物を用いて得られるゴム架橋物を提供することを目的とする。 The present invention was made in view of these circumstances, and provides a nitrile rubber composition that can provide a crosslinked rubber product with low hardness and excellent tensile strength, and a nitrile rubber composition that can provide a crosslinked rubber product with low hardness and excellent tensile strength. The object of the present invention is to provide a rubber crosslinked product obtained using the method.
本発明者等は、上記目的を達成するために鋭意研究した結果、特定量のゴム添加可塑剤を含有する油展ニトリルゴムと、配合用可塑剤と、充填剤とを含有するニトリルゴム組成物を用いることにより、上記目的を達成できることを見出し、本発明を完成させるに至った。 As a result of intensive research to achieve the above object, the present inventors have developed a nitrile rubber composition containing an oil-extended nitrile rubber containing a specific amount of a rubber-added plasticizer, a compounding plasticizer, and a filler. The inventors have discovered that the above object can be achieved by using the following, and have completed the present invention.
すなわち、本発明によれば、油展ニトリルゴムと、配合用可塑剤と、充填剤と、を含むニトリルゴム組成物であって、前記油展ニトリルゴムは、ニトリルゴム成分と、ゴム添加可塑剤とを含み、前記油展ニトリルゴムにおける前記ゴム添加可塑剤の含有割合が、前記油展ニトリルゴム中の前記ニトリルゴム成分１００重量部に対して１５重量部以上であるニトリルゴム組成物が提供される。 That is, according to the present invention, there is provided a nitrile rubber composition comprising an oil-extended nitrile rubber, a compounding plasticizer, and a filler, the oil-extended nitrile rubber comprising a nitrile rubber component and a rubber-added plasticizer. There is provided a nitrile rubber composition comprising: the content of the rubber-added plasticizer in the oil-extended nitrile rubber is 15 parts by weight or more based on 100 parts by weight of the nitrile rubber component in the oil-extended nitrile rubber. Ru.
本発明のニトリルゴム組成物は、前記ゴム添加可塑剤がアジピン酸エーテルエステル系の可塑剤であることが好ましい。 In the nitrile rubber composition of the present invention, the plasticizer added to the rubber is preferably an adipic acid ether ester plasticizer.
本発明のニトリルゴム組成物は、前記ニトリルゴム組成物における前記ゴム添加可塑剤および前記配合用可塑剤の合計の含有割合が、前記油展ニトリルゴム中の前記ニトリルゴム成分１００重量部に対して１８重量部以上であることが好ましい。 In the nitrile rubber composition of the present invention, the total content ratio of the rubber-added plasticizer and the compounding plasticizer in the nitrile rubber composition is based on 100 parts by weight of the nitrile rubber component in the oil-extended nitrile rubber. It is preferably 18 parts by weight or more.
本発明のニトリルゴム組成物は、前記油展ニトリルゴム中の前記ニトリルゴム成分が、アクリロニトリル、ブタジエン、および、イソプレンとの共重合体であることが好ましい。 In the nitrile rubber composition of the present invention, the nitrile rubber component in the oil-extended nitrile rubber is preferably a copolymer of acrylonitrile, butadiene, and isoprene.
また、本発明によれば、前記ニトリルゴム組成物を架橋することにより得られ、デュロメータ硬さ試験により測定される硬さが５０以下であるゴム架橋物が提供される。 Further, according to the present invention, there is provided a crosslinked rubber product obtained by crosslinking the nitrile rubber composition and having a hardness of 50 or less as measured by a durometer hardness test.
本発明によれば、低硬度で、かつ引張強度に優れたゴム架橋物を与えることができるニトリルゴム組成物を提供することができる。 According to the present invention, it is possible to provide a nitrile rubber composition that can provide a crosslinked rubber product with low hardness and excellent tensile strength.
＜ニトリルゴム組成物＞
本発明のニトリルゴム組成物は、油展ニトリルゴムと、配合用可塑剤と、充填剤とを含有する。
<Nitrile rubber composition>
The nitrile rubber composition of the present invention contains oil-extended nitrile rubber, a compounding plasticizer, and a filler.
＜油展ニトリルゴム＞
油展ニトリルゴムは、ニトリルゴム成分と、ゴム添加可塑剤とを含有する。
ニトリルゴム成分は、α，β－エチレン性不飽和ニトリル単量体単位と、共役ジエン単量体単位とを含有する。
<Oil-extended nitrile rubber>
Oil-extended nitrile rubber contains a nitrile rubber component and a rubber-added plasticizer.
The nitrile rubber component contains α,β-ethylenically unsaturated nitrile monomer units and conjugated diene monomer units.
α，β－エチレン性不飽和ニトリル単量体単位を形成するα，β－エチレン性不飽和ニトリル単量体としては、特に限定されないが、ニトリル基を有し、炭素数が、好ましくは３～１８であるエチレン性不飽和化合物を用いることができる。このようなα，β－エチレン性不飽和ニトリル単量体としては、たとえば、アクリロニトリル；α－クロロアクリロニトリル、α－ブロモアクリロニトリルなどのα－ハロゲノアクリロニトリル；メタクリロニトリル、エタクリロニトリルなどのα－アルキルアクリロニトリル；などが挙げられる。これらのなかでも、アクリロニトリルおよびメタクリロニトリルが好ましく、アクリロニトリルが特に好ましい。なお、これらのα，β－エチレン性不飽和ニトリル単量体は、１種単独で用いてもよく、２種以上を組み合わせて用いてもよい。 The α,β-ethylenically unsaturated nitrile monomer forming the α,β-ethylenically unsaturated nitrile monomer unit is not particularly limited, but it has a nitrile group and preferably has 3 to 3 carbon atoms. Ethylenically unsaturated compounds that are 18 can be used. Such α,β-ethylenically unsaturated nitrile monomers include, for example, acrylonitrile; α-halogenoacrylonitrile such as α-chloroacrylonitrile and α-bromoacrylonitrile; α-alkyl such as methacrylonitrile and ethacrylonitrile; Examples include acrylonitrile; and the like. Among these, acrylonitrile and methacrylonitrile are preferred, and acrylonitrile is particularly preferred. Note that these α,β-ethylenically unsaturated nitrile monomers may be used alone or in combination of two or more types.
油展ニトリルゴムに含まれるニトリルゴム成分中における、α，β－エチレン性不飽和ニトリル単量体単位の含有量は、全単量体単位に対して、１５～４８重量％であり、好ましくは２０～４５重量％、より好ましくは２５～４０重量％、特に好ましくは３０～４０重量％である。α，β－エチレン性不飽和ニトリル単量体単位の含有量が少なすぎると、得られるゴム架橋物の耐油性が低下してしまう。一方、α，β－エチレン性不飽和ニトリル単量体単位の含有量が多すぎると、油展ニトリルゴムと配合用可塑剤との親和性が悪くなり、得られるゴム組成物やゴム架橋物から配合用可塑剤が表面に浮き出てしまう（ブリードする）おそれがある。 The content of α,β-ethylenically unsaturated nitrile monomer units in the nitrile rubber component contained in the oil-extended nitrile rubber is 15 to 48% by weight based on the total monomer units, preferably The amount is 20 to 45% by weight, more preferably 25 to 40% by weight, particularly preferably 30 to 40% by weight. If the content of α,β-ethylenically unsaturated nitrile monomer units is too small, the oil resistance of the obtained crosslinked rubber product will be reduced. On the other hand, if the content of α,β-ethylenically unsaturated nitrile monomer units is too large, the affinity between the oil-extended nitrile rubber and the compounding plasticizer will deteriorate, and the resulting rubber composition or rubber crosslinked product will be There is a risk that the plasticizer used in the formulation may rise to the surface (bleed).
共役ジエン単量体単位を形成する共役ジエン単量体としては、特に限定されないが、１，３－ブタジエン、イソプレン、２，３－ジメチル－１，３－ブタジエン、１，３－ペンタジエン、クロロプレンなどの炭素数４～６の共役ジエン単量体が好ましく、１，３－ブタジエンおよびイソプレンがより好ましく、１，３－ブタジエンまたは１，３－ブタジエンおよびイソプレンの組み合わせがさらに好ましく、形状保持性に一層優れたニトリルゴム組成物を得ることができることから、１，３－ブタジエンおよびイソプレンの組み合わせが特に好ましい。なお、これらの共役ジエン単量体は、１種単独で用いてもよく、２種以上を組み合わせて用いてもよい。 Conjugated diene monomers forming the conjugated diene monomer unit include, but are not particularly limited to, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, 1,3-pentadiene, chloroprene, etc. A conjugated diene monomer having 4 to 6 carbon atoms is preferable, 1,3-butadiene and isoprene are more preferable, and 1,3-butadiene or a combination of 1,3-butadiene and isoprene is even more preferable. Particularly preferred is the combination of 1,3-butadiene and isoprene, since superior nitrile rubber compositions can be obtained. In addition, these conjugated diene monomers may be used individually by 1 type, and may be used in combination of 2 or more types.
共役ジエン単量体単位を形成するために、１，３－ブタジエンとイソプレンとを組み合わせて用いる場合の、１，３－ブタジエン単位とイソプレン単位との重量比（１，３－ブタジエン単位／イソプレン単位）としては、好ましくは５０／５０～９０／１０であり、より好ましくは６０／４０～９０／１０であり、特に好ましくは７０／３０～８５／１５である。 When 1,3-butadiene and isoprene are used in combination to form a conjugated diene monomer unit, the weight ratio of 1,3-butadiene units to isoprene units (1,3-butadiene units/isoprene units) ) is preferably 50/50 to 90/10, more preferably 60/40 to 90/10, particularly preferably 70/30 to 85/15.
油展ニトリルゴムに含まれるニトリルゴム成分中における、共役ジエン単量体単位の含有量は、全単量体単位に対して、好ましくは４５～８５重量％、より好ましくは５５～８０重量％、特に好ましくは６０～７５重量％である。共役ジエン単量体単位の含有量を上記範囲にすることにより、得られるゴム架橋物を、良好なゴム弾性を保ちながら、機械的特性に優れたものとすることができる。 The content of conjugated diene monomer units in the nitrile rubber component contained in the oil-extended nitrile rubber is preferably 45 to 85% by weight, more preferably 55 to 80% by weight, based on the total monomer units. Particularly preferred is 60 to 75% by weight. By controlling the content of the conjugated diene monomer unit within the above range, the crosslinked rubber product obtained can have excellent mechanical properties while maintaining good rubber elasticity.
油展ニトリルゴムに含まれるニトリルゴム成分は、α，β－エチレン性不飽和ニトリル単量体単位および共役ジエン単量体単位に加えて、これらの単量体単位を形成する単量体と共重合可能なその他の単量体の単位を含有していてもよい。 The nitrile rubber component contained in the oil-extended nitrile rubber includes, in addition to α,β-ethylenically unsaturated nitrile monomer units and conjugated diene monomer units, the nitrile rubber component contained in the oil-extended nitrile rubber contains monomers that form these monomer units. It may also contain units of other polymerizable monomers.
このようなその他の単量体としては、α－オレフィン単量体、非共役ジエン単量体、芳香族ビニル単量体、α，β－エチレン性不飽和モノカルボン酸およびそのエステル、α，β－エチレン性不飽和多価カルボン酸ならびにそのモノエステル、多価エステルおよび無水物、架橋性単量体、フッ素含有ビニル単量体、共重合性老化防止剤などが挙げられる。 Such other monomers include α-olefin monomers, non-conjugated diene monomers, aromatic vinyl monomers, α, β-ethylenically unsaturated monocarboxylic acids and their esters, α, β - Ethylenically unsaturated polycarboxylic acids and their monoesters, polyesters and anhydrides, crosslinkable monomers, fluorine-containing vinyl monomers, copolymerizable anti-aging agents, etc.
α－オレフィン単量体としては、好ましくは炭素数が２～１２のものであり、エチレン、プロピレン、１－ブテン、４－メチル－１－ペンテン、１－ヘキセン、１－オクテンなどが例示される。 The α-olefin monomer preferably has 2 to 12 carbon atoms, and examples thereof include ethylene, propylene, 1-butene, 4-methyl-1-pentene, 1-hexene, and 1-octene. .
非共役ジエン単量体としては、炭素数が５～１２のものが好ましく、たとえば、１，４－ペンタジエン、１，４－ヘキサジエン、ビニルノルボルネン、ジシクロペンタジエンなどが挙げられる。 The non-conjugated diene monomer preferably has 5 to 12 carbon atoms, and includes, for example, 1,4-pentadiene, 1,4-hexadiene, vinylnorbornene, dicyclopentadiene, and the like.
芳香族ビニル単量体としては、たとえば、スチレン、α－メチルスチレン、ビニルピリジンなどが挙げられる。 Examples of the aromatic vinyl monomer include styrene, α-methylstyrene, and vinylpyridine.
α，β－エチレン性不飽和モノカルボン酸としては、たとえば、アクリル酸、メタクリル酸、クロトン酸、ケイ皮酸などが好ましく挙げられる。
α，β－エチレン性不飽和モノカルボン酸エステルとしては、たとえば、アクリル酸メチル、アクリル酸エチル、アクリル酸ｎ－ブチル、アクリル酸イソブチル、アクリル酸ｎ－ドデシル、メタクリル酸メチル、メタクリル酸エチルなどの炭素数１～１８のアルキル基を有する（メタ）アクリル酸エステル（「メタクリル酸エステルおよびアクリル酸エステル」の略記。以下同様。）；アクリル酸メトキシメチル、アクリル酸メトキシエチル、アクリル酸エトキシプロピル、アクリル酸メトキシブチル、アクリル酸エトキシドデシル、メタクリル酸メトキシエチル、メタクリル酸メトキシブチル、メタクリル酸エトキシペンチルなどの炭素数２～１８のアルコキシアルキル基を有する（メタ）アクリル酸エステル；アクリル酸α－シアノエチル、メタクリル酸α－シアノエチル、メタクリル酸シアノブチルなどの炭素数２～１２のシアノアルキル基を有する（メタ）アクリル酸エステル；アクリル酸２－ヒドロキシエチル、アクリル酸２－ヒドロキシプロピル、メタクリル酸２－ヒドロキシエチルなどの炭素数１～１２のヒドロキシアルキル基を有する（メタ）アクリル酸エステル；アクリル酸トリフルオロエチル、メタクリル酸テトラフルオロプロピルなどの炭素数１～１２のフルオロアルキル基を有する（メタ）アクリル酸エステル；などが挙げられる。
Preferred examples of the α,β-ethylenically unsaturated monocarboxylic acid include acrylic acid, methacrylic acid, crotonic acid, and cinnamic acid.
Examples of α,β-ethylenically unsaturated monocarboxylic acid esters include methyl acrylate, ethyl acrylate, n-butyl acrylate, isobutyl acrylate, n-dodecyl acrylate, methyl methacrylate, and ethyl methacrylate. (Meth)acrylic acid ester having an alkyl group having 1 to 18 carbon atoms (abbreviation for “methacrylic acid ester and acrylic acid ester”; the same applies hereinafter); methoxymethyl acrylate, methoxyethyl acrylate, ethoxypropyl acrylate, acrylic (Meth)acrylic esters having an alkoxyalkyl group having 2 to 18 carbon atoms, such as methoxybutyl acrylate, ethoxydodecyl acrylate, methoxyethyl methacrylate, methoxybutyl methacrylate, and ethoxypentyl methacrylate; α-cyanoethyl acrylate, methacrylate (meth)acrylic acid esters having a cyanoalkyl group having 2 to 12 carbon atoms such as α-cyanoethyl acrylate and cyanobutyl methacrylate; 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2-hydroxyethyl methacrylate, etc. (Meth)acrylic esters having a hydroxyalkyl group having 1 to 12 carbon atoms; (meth)acrylic esters having a fluoroalkyl group having 1 to 12 carbon atoms such as trifluoroethyl acrylate and tetrafluoropropyl methacrylate; etc. can be mentioned.
α，β－エチレン性不飽和多価カルボン酸としては、たとえば、マレイン酸、フマル酸、イタコン酸などが挙げられる。
α，β－エチレン性不飽和多価カルボン酸モノエステルとしては、たとえば、マレイン酸モノメチル、マレイン酸モノエチル、マレイン酸モノプロピル、マレイン酸モノｎ－ブチルなどのマレイン酸モノアルキルエステル；マレイン酸モノシクロペンチル、マレイン酸モノシクロヘキシル、マレイン酸モノシクロヘプチルなどのマレイン酸モノシクロアルキルエステル；マレイン酸モノメチルシクロペンチル、マレイン酸モノエチルシクロヘキシルなどのマレイン酸モノアルキルシクロアルキルエステル；フマル酸モノメチル、フマル酸モノエチル、フマル酸モノプロピル、フマル酸モノｎ－ブチルなどのフマル酸モノアルキルエステル；フマル酸モノシクロペンチル、フマル酸モノシクロヘキシル、フマル酸モノシクロヘプチルなどのフマル酸モノシクロアルキルエステル；フマル酸モノメチルシクロペンチル、フマル酸モノエチルシクロヘキシルなどのフマル酸モノアルキルシクロアルキルエステル；シトラコン酸モノメチル、シトラコン酸モノエチル、シトラコン酸モノプロピル、シトラコン酸モノｎ－ブチルなどのシトラコン酸モノアルキルエステル；シトラコン酸モノシクロペンチル、シトラコン酸モノシクロヘキシル、シトラコン酸モノシクロヘプチルなどのシトラコン酸モノシクロアルキルエステル；シトラコン酸モノメチルシクロペンチル、シトラコン酸モノエチルシクロヘキシルなどのシトラコン酸モノアルキルシクロアルキルエステル；イタコン酸モノメチル、イタコン酸モノエチル、イタコン酸モノプロピル、イタコン酸モノｎ－ブチルなどのイタコン酸モノアルキルエステル；イタコン酸モノシクロペンチル、イタコン酸モノシクロヘキシル、イタコン酸モノシクロヘプチルなどのイタコン酸モノシクロアルキルエステル；イタコン酸モノメチルシクロペンチル、イタコン酸モノエチルシクロヘキシルなどのイタコン酸モノアルキルシクロアルキルエステル；などが挙げられる。
α，β－エチレン性不飽和多価カルボン酸多価エステルとしては、たとえば、マレイン酸ジメチル、マレイン酸ジｎ－ブチル、フマル酸ジメチル、フマル酸ジｎ－ブチル、イタコン酸ジメチル、イタコン酸ジｎ－ブチルなどが挙げられる。
α，β－エチレン性不飽和多価カルボン酸無水物としては、たとえば、無水マレイン酸、無水イタコン酸などが挙げられる。
Examples of the α,β-ethylenically unsaturated polycarboxylic acid include maleic acid, fumaric acid, and itaconic acid.
Examples of α,β-ethylenically unsaturated polycarboxylic acid monoester include monoalkyl maleate such as monomethyl maleate, monoethyl maleate, monopropyl maleate, and mono-n-butyl maleate; monocyclopentyl maleate. , monocyclohexyl maleate, monocycloheptyl maleate, etc.; monoalkyl cycloalkyl maleate esters, such as monomethylcyclopentyl maleate, monoethylcyclohexyl maleate; monomethyl fumarate, monoethyl fumarate, fumaric acid. Fumaric acid monoalkyl esters such as monopropyl and mono-n-butyl fumarate; fumaric acid monocycloalkyl esters such as monocyclopentyl fumarate, monocyclohexyl fumarate, and monocycloheptyl fumarate; monomethylcyclopentyl fumarate, monoethyl fumarate Fumaric acid monoalkyl cycloalkyl esters such as cyclohexyl; citraconic acid monoalkyl esters such as monomethyl citraconate, monoethyl citraconate, monopropyl citraconate, mono-n-butyl citraconate; monocyclopentyl citraconate, monocyclohexyl citraconate, citraconic acid Citraconic acid monocycloalkyl esters such as monocycloheptyl; citraconic acid monoalkylcycloalkyl esters such as monomethylcyclopentyl citraconate, monoethylcyclohexyl citraconate; monomethyl itaconate, monoethyl itaconate, monopropyl itaconate, mono n- itaconate Itaconate monoalkyl esters such as butyl; itaconate monocycloalkyl esters such as monocyclopentyl itaconate, monocyclohexyl itaconate, and monocycloheptyl itaconate; itaconate monocycloalkyl esters such as monomethylcyclopentyl itaconate, monoethylcyclohexyl itaconate, etc. Examples include alkyl esters; and the like.
Examples of α,β-ethylenically unsaturated polycarboxylic acid polyesters include dimethyl maleate, di-n-butyl maleate, dimethyl fumarate, di-n-butyl fumarate, dimethyl itaconate, di-n-itaconate, - Examples include butyl.
Examples of the α,β-ethylenically unsaturated polycarboxylic acid anhydride include maleic anhydride and itaconic anhydride.
架橋性単量体としては、たとえば、ジビニルベンゼンなどのジビニル化合物；エチレンジ（メタ）アクリレート、ジエチレングリコールジ（メタ）アクリレート、ポリエチレングリコールジ（メタ）アクリレートなどのジ（メタ）アクリル酸エステル類；トリメチロールプロパントリ（メタ）アクリレートなどのトリメタクリル酸エステル類；などの多官能エチレン性不飽和単量体のほか、Ｎ－メチロール（メタ）アクリルアミド、Ｎ，Ｎ’－ジメチロール（メタ）アクリルアミドなどの自己架橋性単量体などが挙げられる。 Examples of crosslinkable monomers include divinyl compounds such as divinylbenzene; di(meth)acrylic acid esters such as ethylene di(meth)acrylate, diethylene glycol di(meth)acrylate, and polyethylene glycol di(meth)acrylate; trimethylol; In addition to polyfunctional ethylenically unsaturated monomers such as trimethacrylic acid esters such as propane tri(meth)acrylate, self-crosslinking such as N-methylol(meth)acrylamide and N,N'-dimethylol(meth)acrylamide Examples include sexual monomers.
フッ素含有ビニル単量体としては、フルオロエチルビニルエーテル、フルオロプロピルビニルエーテル、ｏ－トリフルオロメチルスチレン、ペンタフルオロ安息香酸ビニル、ジフルオロエチレン、テトラフルオロエチレンなどが挙げられる。 Examples of the fluorine-containing vinyl monomer include fluoroethyl vinyl ether, fluoropropyl vinyl ether, o-trifluoromethylstyrene, vinyl pentafluorobenzoate, difluoroethylene, and tetrafluoroethylene.
共重合性老化防止剤としては、たとえば、Ｎ－（４－アニリノフェニル）アクリルアミド、Ｎ－（４－アニリノフェニル）メタクリルアミド、Ｎ－（４－アニリノフェニル）シンナムアミド、Ｎ－（４－アニリノフェニル）クロトンアミド、 Ｎ－フェニル－４－（３－ビニルベンジルオキシ）アニリン、Ｎ－フェニル－４－（４－ビニルベンジルオキシ）アニリンなどが挙げられる。 Examples of copolymerizable anti-aging agents include N-(4-anilinophenyl)acrylamide, N-(4-anilinophenyl)methacrylamide, N-(4-anilinophenyl)cinnamamide, and N-(4-anilinophenyl)methacrylamide. Examples include anilinophenyl)crotonamide, N-phenyl-4-(3-vinylbenzyloxy)aniline, and N-phenyl-4-(4-vinylbenzyloxy)aniline.
これらの共重合可能なその他の単量体として、複数種類を併用してもよい。
油展ニトリルゴムに含まれるニトリルゴム成分中における、その他の単量体の単位の含有量は、全単量体単位に対して、好ましくは２０重量％以下、より好ましくは１０重量％以下、特に好ましくは５重量％以下である。
As these other copolymerizable monomers, a plurality of types may be used in combination.
The content of other monomer units in the nitrile rubber component contained in the oil-extended nitrile rubber is preferably 20% by weight or less, more preferably 10% by weight or less, particularly Preferably it is 5% by weight or less.
本発明で用いられる油展ニトリルゴムは、上記ニトリルゴム成分に対して、あらかじめ添加されたゴム添加可塑剤を含有する。すなわち、本発明で用いられる油展ニトリルゴムは、ゴム添加可塑剤を油展油として含有する油展ゴムである。ゴム添加可塑剤としては、ゴム用の可塑剤として一般的に用いられているものであればよく、特に限定されないが、ジカルボン酸とエーテル結合含有アルコールとのエステル化合物であることが好ましい。油展ニトリルゴムに、予め添加するゴム添加可塑剤として、ジカルボン酸とエーテル結合含有アルコールとのエステル化合物を含有することから、本発明のニトリルゴム組成物は、低硬度で、かつ、優れた引張強度を有するゴム架橋物を得ることができる。 The oil-extended nitrile rubber used in the present invention contains a rubber-added plasticizer added in advance to the nitrile rubber component. That is, the oil-extended nitrile rubber used in the present invention is an oil-extended rubber containing a rubber-added plasticizer as an oil-extending oil. The rubber-added plasticizer may be any one commonly used as a plasticizer for rubber, and is not particularly limited, but is preferably an ester compound of a dicarboxylic acid and an ether bond-containing alcohol. Since the oil-extended nitrile rubber contains an ester compound of a dicarboxylic acid and an ether bond-containing alcohol as a rubber additive plasticizer, the nitrile rubber composition of the present invention has low hardness and excellent tensile strength. A crosslinked rubber product with strength can be obtained.
エステル化合物を形成するジカルボン酸としては、下記一般式（１）で表されるジカルボン酸が挙げられる。
ＨＯＯＣＲＣＯＯＨ （１）
（式中のＲは炭素数２～１０のアルキレン基を表し、ＣＯＯＨはカルボキシ基を表す。）
Examples of dicarboxylic acids that form ester compounds include dicarboxylic acids represented by the following general formula (1).
HOOCRCOOH (1)
(R in the formula represents an alkylene group having 2 to 10 carbon atoms, and COOH represents a carboxy group.)
式（１）中のＲとしては、直鎖状または分岐鎖状のアルキレン基であってよいが、直鎖状のアルキレン基が好ましい。また、アルキレン基の炭素数は、好ましくは２～１０であり、より好ましくは４～８である。 R in formula (1) may be a linear or branched alkylene group, but a linear alkylene group is preferred. Further, the alkylene group preferably has 2 to 10 carbon atoms, more preferably 4 to 8 carbon atoms.
エステル化合物を形成するジカルボン酸としては、コハク酸、グルタル酸、アジピン酸、ピメリン酸、スベリン酸、アゼライン酸、セバチン酸などが挙げられ、中でもアジピン酸が好ましい。 Examples of the dicarboxylic acid that forms the ester compound include succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, and sebacic acid, of which adipic acid is preferred.
エステル化合物を形成するエーテル結合含有アルコールとしては、一価のアルコールが好ましい。また、エーテル結合含有アルコールの炭素数は、好ましくは４～１０であり、より好ましくは６～８である。エーテル結合含有アルコールに含有されるエーテル結合の数は、好ましくは１～４、より好ましくは１～２である。 The ether bond-containing alcohol that forms the ester compound is preferably a monohydric alcohol. Further, the number of carbon atoms in the ether bond-containing alcohol is preferably 4 to 10, more preferably 6 to 8. The number of ether bonds contained in the ether bond-containing alcohol is preferably 1 to 4, more preferably 1 to 2.
エステル化合物としては、ジカルボン酸とエーテル結合含有アルコールとを任意に組み合わせて得られるものを用いることができる。通常、モノエステル化合物およびジエステル化合物が用いられるが、好ましいのはジエステル化合物である。エステル化合物としては、好ましくはアジピン酸エーテルエステル化合物が用いられる。すなわち、ゴム添加可塑剤としては、好ましくはアジピン酸エーテルエステル系の可塑剤が用いられる。 As the ester compound, one obtained by arbitrarily combining a dicarboxylic acid and an ether bond-containing alcohol can be used. Usually, monoester compounds and diester compounds are used, but diester compounds are preferred. As the ester compound, preferably an adipic acid ether ester compound is used. That is, as the rubber-added plasticizer, preferably an adipic acid ether ester plasticizer is used.
油展ニトリルゴム中のゴム添加可塑剤の含有量は、ニトリルゴム成分１００重量部に対して、１５重量部以上である。油展ニトリルゴム中のゴム添加可塑剤の含有量の上限は、特に限定されないが、好ましくは１００重量部以下であり、より好ましくは５０重量部以下であり、さらに好ましくは４０重量部以下である。ゴム添加可塑剤の含有量が少なすぎると、得られるニトリルゴム組成物の加工性（添加剤の混合容易性）が劣るため、得られるニトリルゴム組成物の成形性に劣り、得られるゴム架橋物の引張応力が劣る。また、ゴム添加可塑剤の含有量が多すぎると、得られるニトリルゴム組成物の形状保持性が劣る。 The content of the rubber-added plasticizer in the oil-extended nitrile rubber is 15 parts by weight or more based on 100 parts by weight of the nitrile rubber component. The upper limit of the content of the rubber-added plasticizer in the oil-extended nitrile rubber is not particularly limited, but is preferably 100 parts by weight or less, more preferably 50 parts by weight or less, and even more preferably 40 parts by weight or less. . If the content of the rubber additive plasticizer is too low, the processability of the resulting nitrile rubber composition (ease of mixing additives) will be poor, and the moldability of the resulting nitrile rubber composition will be poor, resulting in a rubber crosslinked product. The tensile stress is inferior. Moreover, if the content of the rubber-added plasticizer is too large, the shape retention of the resulting nitrile rubber composition will be poor.
油展ニトリルゴムのムーニー粘度（ＭＬ１＋４，１００℃）は、好ましくは１０～２００、より好ましくは２０～１５０、さらに好ましくは４０～１００である。油展ニトリルゴムのムーニー粘度を上記範囲とすることにより、良好な常態物性を有するゴム架橋物を与えることのできるニトリルゴム組成物を得ることができる。 The oil-extended nitrile rubber has a Mooney viscosity (ML1+4, 100°C) of preferably 10 to 200, more preferably 20 to 150, and still more preferably 40 to 100. By controlling the Mooney viscosity of the oil-extended nitrile rubber within the above range, it is possible to obtain a nitrile rubber composition capable of providing a rubber crosslinked product having good normal physical properties.
＜配合用可塑剤＞
本発明のニトリルゴム組成物は、上記した油展ニトリルゴムに、配合用可塑剤および充填剤を含有するものである。すなわち、本発明のニトリルゴム組成物は、上記した油展ニトリルゴムに含まれるゴム添加可塑剤に加えて、配合用可塑剤をさらに配合し、かつ、これに充填剤を配合することにより得られるものである。
<Plasticizer for compounding>
The nitrile rubber composition of the present invention contains the above-mentioned oil-extended nitrile rubber, a blending plasticizer, and a filler. That is, the nitrile rubber composition of the present invention is obtained by further blending a compounding plasticizer in addition to the rubber-added plasticizer contained in the oil-extended nitrile rubber described above, and also blending a filler therewith. It is something.
配合用可塑剤は、ゴム用の可塑剤として一般的に用いられているものであればよく、特に限定されないが、ジカルボン酸とエーテル結合含有アルコールとのエステル化合物であることが好ましい。配合用可塑剤として用いられる、ジカルボン酸とエーテル結合含有アルコールとのエステル化合物としては、上述したゴム添加可塑剤として用いられるジカルボン酸とエーテル結合含有アルコールとのエステル化合物として例示したものと同様のものを選択することができる。 The compounding plasticizer may be any one commonly used as a plasticizer for rubber, and is not particularly limited, but is preferably an ester compound of a dicarboxylic acid and an ether bond-containing alcohol. The ester compound of dicarboxylic acid and ether bond-containing alcohol used as a compounding plasticizer is the same as the one exemplified above as the ester compound of dicarboxylic acid and ether bond-containing alcohol used as the rubber additive plasticizer. can be selected.
本発明のニトリルゴム組成物中における、配合用可塑剤の含有量は、特に限定されないが、油展ニトリルゴム中に含まれるニトリルゴム成分１００重量部に対して、好ましくは３重量部以上であり、より好ましくは１０重量部以上であり、さらに好ましくは２０重量部以上である。 The content of the compounding plasticizer in the nitrile rubber composition of the present invention is not particularly limited, but is preferably 3 parts by weight or more based on 100 parts by weight of the nitrile rubber component contained in the oil-extended nitrile rubber. , more preferably 10 parts by weight or more, still more preferably 20 parts by weight or more.
本発明のニトリルゴム組成物中に含まれるゴム添加可塑剤および配合用可塑剤の合計の含有量は、油展ニトリルゴム中に含まれるニトリルゴム成分１００重量部に対して、１８重量部以上であり、好ましくは３０重量部以上であり、より好ましくは４５重量部以上である。ゴム添加可塑剤および配合用可塑剤の合計の含有量の上限は、特に限定されないが、油展ニトリルゴム中に含まれるニトリルゴム成分１００重量部に対して、好ましくは１１０重量部以下であり、より好ましくは８５重量部以下であり、さらに好ましくは７０重量部以下である。 The total content of the rubber additive plasticizer and the compounding plasticizer contained in the nitrile rubber composition of the present invention is 18 parts by weight or more based on 100 parts by weight of the nitrile rubber component contained in the oil-extended nitrile rubber. The amount is preferably 30 parts by weight or more, more preferably 45 parts by weight or more. The upper limit of the total content of the rubber additive plasticizer and the compounding plasticizer is not particularly limited, but is preferably 110 parts by weight or less with respect to 100 parts by weight of the nitrile rubber component contained in the oil-extended nitrile rubber. More preferably it is 85 parts by weight or less, and even more preferably 70 parts by weight or less.
＜充填剤＞
また、本発明のニトリルゴム組成物は、上記した油展ニトリルゴムおよび配合用可塑剤に加えて、充填剤を含有する。充填剤としては、ゴム分野において通常用いられている充填剤であれば何でもよく特に限定されず、有機充填剤および無機充填剤のいずれをも用いることができるが、その配合効果が高いという点より、無機充填剤が好ましい。
<Filler>
Further, the nitrile rubber composition of the present invention contains a filler in addition to the above-described oil-extended nitrile rubber and a compounding plasticizer. The filler may be any filler that is commonly used in the rubber field and is not particularly limited. Both organic fillers and inorganic fillers can be used, but from the viewpoint of their high blending effect. , inorganic fillers are preferred.
無機充填剤としては、ゴムの配合用に通常用いられているものであればよく、たとえば、カーボンブラック、シリカ、クレー、アルミナ、水酸化アルミニウム、酸化マグネシウム、水酸化マグネシウム、酸化カルシウム、水酸化カルシウム、酸化アルミニウムマグネシウム、酸化チタン、カオリン、パイロフィライト、ベントナイト、タルク、アタパルジャイト、ケイ酸マグネシウムカルシウム、ケイ酸アルミニウム、ケイ酸マグネシウム、ケイ酸カルシウム、結晶性アルミノケイ酸塩などが挙げられる。これらのなかでも、好ましくはカーボンブラック、シリカ、クレーが用いられ、より好ましくはシリカが用いられる。無機充填剤は、１種単独で、または複数種併せて用いることができる。 Inorganic fillers may be those commonly used for rubber compounding, such as carbon black, silica, clay, alumina, aluminum hydroxide, magnesium oxide, magnesium hydroxide, calcium oxide, and calcium hydroxide. , aluminum magnesium oxide, titanium oxide, kaolin, pyrophyllite, bentonite, talc, attapulgite, magnesium calcium silicate, aluminum silicate, magnesium silicate, calcium silicate, crystalline aluminosilicate, and the like. Among these, carbon black, silica, and clay are preferably used, and silica is more preferably used. The inorganic fillers can be used alone or in combination.
カーボンブラックとしては、ゴムの配合用に通常用いられているものであればよく、たとえば、ファーネスブラック、アセチレンブラック、サーマルブラック、チャンネルブラック、およびグラファイトなどが挙げられる。 The carbon black may be any carbon black that is commonly used for compounding rubber, such as furnace black, acetylene black, thermal black, channel black, and graphite.
シリカとしては、石英粉末、珪石粉末などの天然シリカ；無水珪酸（シリカゲル、アエロジルなど）、含水珪酸などの合成シリカ；などが挙げられ、これらの中でも、合成シリカが好ましい。またこれらシリカはカップリング剤等で表面処理されたものであってもよい。 Examples of the silica include natural silica such as quartz powder and silica powder; synthetic silica such as anhydrous silicic acid (such as silica gel and Aerosil) and hydrous silicic acid; among these, synthetic silica is preferred. Moreover, these silicas may be surface-treated with a coupling agent or the like.
クレーとしては、含水ケイ酸アルミニウムを主成分とする天然鉱物であればよく、特に限定されないが、モンモリロナイト、パイロフィライト、カオリナイト、ハロイサイトおよびセリサイトなどが挙げられる。 The clay may be any natural mineral whose main component is hydrated aluminum silicate, and examples thereof include, but are not limited to, montmorillonite, pyrophyllite, kaolinite, halloysite, and sericite.
本発明のニトリルゴム組成物中の充填剤の含有量は、油展ニトリルゴム中に含まれるニトリルゴム成分１００重量部に対して、好ましくは１～２００重量部、より好ましくは１５～１５０重量部、特に好ましくは３０～１００重量部である。 The content of the filler in the nitrile rubber composition of the present invention is preferably 1 to 200 parts by weight, more preferably 15 to 150 parts by weight, based on 100 parts by weight of the nitrile rubber component contained in the oil-extended nitrile rubber. , particularly preferably 30 to 100 parts by weight.
また、本発明のニトリルゴム組成物には、油展ニトリルゴム、配合用可塑剤および可塑剤に加えて、ゴム分野において通常使用される配合剤、たとえば、炭酸カルシウム、タルクやクレーなどの充填剤、酸化亜鉛や酸化マグネシウムなどの金属酸化物、メタクリル酸亜鉛やアクリル酸亜鉛などのα，β－エチレン性不飽和カルボン酸金属塩、共架橋剤、架橋助剤、架橋遅延剤、酸化防止剤、光安定剤、一級アミンなどのスコーチ防止剤、ジエチレングリコールなどの活性剤、カップリング剤、加工助剤、滑剤、粘着剤、潤滑剤、難燃剤、防黴剤、受酸剤、帯電防止剤、顔料、発泡剤などを配合することができる。これらの配合剤の配合量は、本発明の目的や効果を阻害しない範囲であれば特に限定されず、配合目的に応じた量を配合することができる。 In addition to oil-extended nitrile rubber, a compounding plasticizer, and a plasticizer, the nitrile rubber composition of the present invention also contains compounding agents commonly used in the rubber field, such as fillers such as calcium carbonate, talc, and clay. , metal oxides such as zinc oxide and magnesium oxide, α,β-ethylenically unsaturated carboxylic acid metal salts such as zinc methacrylate and zinc acrylate, co-crosslinking agents, crosslinking aids, crosslinking retarders, antioxidants, Light stabilizers, anti-scorch agents such as primary amines, activators such as diethylene glycol, coupling agents, processing aids, lubricants, adhesives, lubricants, flame retardants, anti-mold agents, acid acceptors, antistatic agents, pigments , a foaming agent, etc. can be added. The amount of these ingredients to be blended is not particularly limited as long as it does not impede the purpose or effect of the present invention, and the amount can be blended in accordance with the purpose of blending.
＜油展ニトリルゴム以外のゴム＞
本発明のニトリルゴム組成物には、上記した油展ニトリルゴム以外のゴムを配合してもよい。このようなゴムとしては、可塑剤を含有しない非油展ニトリルゴム、アクリルゴム、エチレン－アクリル酸共重合体ゴム、スチレン－ブタジエン共重合体ゴム、ポリブタジエンゴム、エチレン－プロピレン共重合体ゴム、エチレン－プロピレン－ジエン三元共重合体ゴム、エピクロロヒドリンゴム、フッ素ゴム、ウレタンゴム、クロロプレンゴム、シリコーンゴム、天然ゴム、ポリイソプレンゴムなどが挙げられる。
<Rubbers other than oil-extended nitrile rubber>
The nitrile rubber composition of the present invention may contain rubbers other than the oil-extended nitrile rubbers described above. Such rubbers include non-oil extended nitrile rubber containing no plasticizer, acrylic rubber, ethylene-acrylic acid copolymer rubber, styrene-butadiene copolymer rubber, polybutadiene rubber, ethylene-propylene copolymer rubber, and ethylene. Examples include -propylene-diene terpolymer rubber, epichlorohydrin rubber, fluororubber, urethane rubber, chloroprene rubber, silicone rubber, natural rubber, and polyisoprene rubber.
油展ニトリルゴム以外のゴムを配合する場合における、ニトリルゴム組成物中の油展ニトリルゴム以外のゴムの配合量は、油展ニトリルゴム中に含まれるニトリルゴム成分１００重量部に対して、好ましくは２３０重量部以下、より好ましくは１００重量部以下、さらに好ましくは６５重量部以下である。 When a rubber other than oil-extended nitrile rubber is blended, the amount of the rubber other than oil-extended nitrile rubber in the nitrile rubber composition is preferably based on 100 parts by weight of the nitrile rubber component contained in the oil-extended nitrile rubber. is 230 parts by weight or less, more preferably 100 parts by weight or less, even more preferably 65 parts by weight or less.
油展ニトリルゴム以外のゴムを配合する場合における、ニトリルゴム組成物中の配合用可塑剤の含有量は、特に限定されないが、油展ニトリルゴムおよび油展ニトリルゴム以外のゴムに含まれる全ゴム成分１００重量部に対して、好ましくは１０重量部以上、より好ましくは２０重量部以上である。 When compounding a rubber other than oil-extended nitrile rubber, the content of the plasticizer for compounding in the nitrile rubber composition is not particularly limited, but the total rubber contained in the oil-extended nitrile rubber and the rubber other than oil-extended nitrile rubber is not particularly limited. The amount is preferably 10 parts by weight or more, more preferably 20 parts by weight or more, based on 100 parts by weight of the components.
油展ニトリルゴム以外のゴムを配合する場合における、ニトリルゴム組成物中に含まれるゴム添加可塑剤および配合用可塑剤の合計の含有量は、油展ニトリルゴムおよび油展ニトリルゴム以外のゴムに含まれる全ゴム成分１００重量部に対して、１８重量部以上であり、好ましくは３０重量部以上であり、より好ましくは４５重量部以上である。ゴム添加可塑剤および配合用可塑剤の合計の含有量の上限は、特に限定されないが、油展ニトリルゴム中に含まれるニトリルゴム成分１００重量部に対して、好ましくは１１０重量部以下であり、より好ましくは８５重量部以下であり、さらに好ましくは７０重量部以下である。 When compounding a rubber other than oil-extended nitrile rubber, the total content of the rubber-added plasticizer and the compounding plasticizer contained in the nitrile rubber composition is The amount is 18 parts by weight or more, preferably 30 parts by weight or more, and more preferably 45 parts by weight or more, based on 100 parts by weight of all the rubber components contained. The upper limit of the total content of the rubber additive plasticizer and the compounding plasticizer is not particularly limited, but is preferably 110 parts by weight or less with respect to 100 parts by weight of the nitrile rubber component contained in the oil-extended nitrile rubber. More preferably it is 85 parts by weight or less, and even more preferably 70 parts by weight or less.
本発明のニトリルゴム組成物は、上記した各成分を好ましくは非水系で混合することで調製される。本発明のニトリルゴム組成物を調製する方法に限定はないが、通常、架橋剤および熱に不安定な成分を除いた成分を、バンバリーミキサ、インターミキサ、ニーダーなどの混合機で混練することにより調製できる。混練は、通常、１０～２００℃、好ましくは３０～１８０℃の温度で、１分間～１時間、好ましくは１分間～３０分間行う。 The nitrile rubber composition of the present invention is prepared by mixing the above-mentioned components, preferably in a non-aqueous system. There is no limitation on the method for preparing the nitrile rubber composition of the present invention, but usually, the components excluding the crosslinking agent and heat-labile components are kneaded in a mixer such as a Banbury mixer, an intermixer, or a kneader. Can be prepared. Kneading is usually carried out at a temperature of 10 to 200°C, preferably 30 to 180°C, for 1 minute to 1 hour, preferably 1 minute to 30 minutes.
＜ゴム架橋物＞
本発明のゴム架橋物は、上述した本発明の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、本発明のニトリルゴム組成物をオープンロールなどに移して架橋剤や熱に不安定な成分を加えて混錬して得られた架橋性ゴム組成物を用い、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。混練は、通常、１０～９０℃、好ましくは２０～６０℃の温度で、１分間～１時間、好ましくは１分間～３０分間行う。
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。
<Rubber crosslinked product>
The crosslinked rubber product of the present invention is obtained by crosslinking the nitrile rubber composition of the present invention described above.
The rubber crosslinked product of the present invention is obtained by transferring the nitrile rubber composition of the present invention to an open roll or the like, adding a crosslinking agent and a heat-unstable component, and kneading the resulting crosslinkable rubber composition. It can be manufactured by molding with a molding machine compatible with the shape of the product, such as an extruder, injection molding machine, compressor, roll, etc., and then heating to cause a crosslinking reaction and fixing the shape as a crosslinked product. can. Kneading is usually carried out at a temperature of 10 to 90°C, preferably 20 to 60°C, for 1 minute to 1 hour, preferably 1 minute to 30 minutes.
In this case, the crosslinking may be performed after pre-forming or at the same time as the molding. The molding temperature is usually 10 to 200°C, preferably 25 to 120°C. The crosslinking temperature is usually 100 to 200°C, preferably 130 to 190°C, and the crosslinking time is usually 1 minute to 24 hours, preferably 2 minutes to 1 hour.
本発明のニトリルゴムと架橋剤とを混錬して得られる架橋性ゴム組成物は、配合物・ムーニー粘度（ＭＬ１＋４、１００℃）が、好ましくは５～８０、より好ましくは１０～６０、さらに好ましくは１５～４０である。架橋性ゴム組成物の配合物・ムーニー粘度を上記範囲とすることにより、良好な常態物性が得られる。 The crosslinkable rubber composition obtained by kneading the nitrile rubber of the present invention and a crosslinking agent has a Mooney viscosity (ML1+4, 100°C) of preferably 5 to 80, more preferably 10 to 60, and Preferably it is 15-40. By controlling the Mooney viscosity of the crosslinkable rubber composition within the above range, good normal physical properties can be obtained.
架橋剤としては、特に限定されず、硫黄系架橋剤、有機過酸化物系架橋剤が挙げられるが、油展ニトリルゴムに含まれるニトリルゴム成分が、カルボキシル基を有する単量体単位を有する場合には、ポリアミン系架橋剤を用いることもできる。架橋剤としては、なかでも、様々な架橋成形方法を取り得るという点で硫黄系架橋剤が好ましい。 The crosslinking agent is not particularly limited, and examples include sulfur-based crosslinking agents and organic peroxide-based crosslinking agents, but when the nitrile rubber component contained in the oil-extended nitrile rubber has a monomer unit having a carboxyl group. A polyamine crosslinking agent can also be used. As the crosslinking agent, sulfur-based crosslinking agents are particularly preferred since various crosslinking molding methods can be used.
硫黄系架橋剤としては、粉末硫黄、硫黄華、沈降性硫黄、コロイド硫黄、表面処理硫黄、不溶性硫黄などの硫黄；塩化硫黄、二塩化硫黄、モルホリンジスルフィド、アルキルフェノールジスルフィド、ジベンゾチアジルジスルフィド、Ｎ，Ｎ’－ジチオ－ビス（ヘキサヒドロ－２Ｈ－アゼノピン－２）、含リンポリスルフィド、高分子多硫化物などの含硫黄化合物；テトラメチルチウラムジスルフィド、ジメチルジチオカルバミン酸セレン、２－（４’－モルホリノジチオ）ベンゾチアゾールなどの硫黄供与性化合物；などが挙げられる。これらは一種単独でまたは複数種併せて用いることができる。 Sulfur-based crosslinking agents include powdered sulfur, sulfur flower, precipitated sulfur, colloidal sulfur, surface-treated sulfur, insoluble sulfur, etc.; sulfur chloride, sulfur dichloride, morpholine disulfide, alkylphenol disulfide, dibenzothiazyl disulfide, N, Sulfur-containing compounds such as N'-dithio-bis(hexahydro-2H-azenopine-2), phosphorus-containing polysulfides, and polymer polysulfides; tetramethylthiuram disulfide, selenium dimethyldithiocarbamate, 2-(4'-morpholinodithio) Examples include sulfur-donating compounds such as benzothiazole. These can be used alone or in combination.
有機過酸化物系架橋剤としては、ジクミルペルオキシド、クメンヒドロペルオキシド、ｔ－ブチルクミルペルオキシド、パラメンタンヒドロペルオキシド、ジ－ｔ－ブチルペルオキシド、１，３－ビス（ｔ－ブチルペルオキシイソプロピル）ベンゼン、１，４－ビス（ｔ－ブチルペルオキシイソプロピル）ベンゼン、１，１－ジ－ｔ－ブチルペルオキシ－３，３－トリメチルシクロヘキサン、４，４－ビス－（ｔ－ブチル－ペルオキシ）－ｎ－ブチルバレレート、２，５－ジメチル－２，５－ジ－ｔ－ブチルペルオキシヘキサン、２，５－ジメチル－２，５－ジ－ｔ－ブチルペルオキシヘキシン－３、１，１－ジ－ｔ－ブチルペルオキシ－３，５，５－トリメチルシクロヘキサン、ｐ－クロロベンゾイルペルオキシド、ｔ－ブチルペルオキシイソプロピルカーボネート、ｔ－ブチルペルオキシベンゾエートなどが挙げられる。これらは一種単独でまたは複数種併せて用いることができる。 Examples of organic peroxide crosslinking agents include dicumyl peroxide, cumene hydroperoxide, t-butylcumyl peroxide, para-menthane hydroperoxide, di-t-butyl peroxide, and 1,3-bis(t-butylperoxyisopropyl)benzene. , 1,4-bis(t-butylperoxyisopropyl)benzene, 1,1-di-t-butylperoxy-3,3-trimethylcyclohexane, 4,4-bis-(t-butyl-peroxy)-n-butyl valerate, 2,5-dimethyl-2,5-di-t-butylperoxyhexane, 2,5-dimethyl-2,5-di-t-butylperoxyhexane-3, 1,1-di-t- Examples include butylperoxy-3,5,5-trimethylcyclohexane, p-chlorobenzoylperoxide, t-butylperoxyisopropyl carbonate, t-butylperoxybenzoate and the like. These can be used alone or in combination.
ポリアミン系架橋剤としては、２つ以上のアミノ基を有する化合物、または、架橋時に２つ以上のアミノ基を有する化合物の形態になるもの、であれば特に限定されないが、脂肪族炭化水素や芳香族炭化水素の複数の水素原子が、アミノ基またはヒドラジド構造（－ＣＯＮＨＮＨ２で表される構造、ＣＯはカルボニル基を表す。）で置換された化合物および架橋時にその化合物の形態になるものが好ましい。その具体例としては、ヘキサメチレンジアミン、ヘキサメチレンジアミンカルバメート、テトラメチレンペンタミン、ヘキサメチレンジアミンシンナムアルデヒド付加物、ヘキサメチレンジアミンジベンゾエート塩などの脂肪族多価アミン類；２，２－ビス｛４－（４－アミノフェノキシ）フェニル｝プロパン、４，４’－メチレンジアニリン、ｍ－フェニレンジアミン、ｐ－フェニレンジアミン、４，４’－メチレンビス（ｏ－クロロアニリン）などの芳香族多価アミン類；イソフタル酸ジヒドラジド、アジピン酸ジヒドラジド、セバシン酸ジヒドラジドなどのヒドラジド構造を２つ以上有する化合物などが挙げられる。これらは一種単独でまたは複数種併せて用いることができる。 The polyamine crosslinking agent is not particularly limited as long as it is a compound having two or more amino groups, or a compound having two or more amino groups upon crosslinking, but aliphatic hydrocarbons and aromatic Compounds in which multiple hydrogen atoms of a group hydrocarbon are substituted with an amino group or a hydrazide structure (a structure represented by -CONHNH 2 , CO represents a carbonyl group), and those that become in the form of the compound upon crosslinking are preferred. . Specific examples include aliphatic polyvalent amines such as hexamethylene diamine, hexamethylene diamine carbamate, tetramethylene pentamine, hexamethylene diamine cinnamaldehyde adduct, hexamethylene diamine dibenzoate salt; 2,2-bis{4 Aromatic polyvalent amines such as -(4-aminophenoxy)phenyl}propane, 4,4'-methylenedianiline, m-phenylenediamine, p-phenylenediamine, 4,4'-methylenebis(o-chloroaniline), etc. Examples include compounds having two or more hydrazide structures such as isophthalic acid dihydrazide, adipic acid dihydrazide, and sebacic acid dihydrazide. These can be used alone or in combination.
本発明のニトリルゴム組成物中における、架橋剤の含有量は特に限定されないが、油展ニトリルゴム中に含まれるニトリルゴム成分１００重量部に対して、好ましくは０．１～１０重量部、より好ましくは０．２～５重量部である。 The content of the crosslinking agent in the nitrile rubber composition of the present invention is not particularly limited, but is preferably 0.1 to 10 parts by weight, more preferably 0.1 to 10 parts by weight, based on 100 parts by weight of the nitrile rubber component contained in the oil-extended nitrile rubber. Preferably it is 0.2 to 5 parts by weight.
架橋剤として硫黄系架橋剤を使用する場合は、架橋助剤として、亜鉛華、グアニジン系架橋促進剤、チアゾール系架橋促進剤、チウラム系架橋促進剤、ジチオカルバミン酸塩系架橋促進剤などを併用することが好ましい。 When using a sulfur-based crosslinking agent as a crosslinking agent, use a zinc white, guanidine-based crosslinking accelerator, thiazole-based crosslinking accelerator, thiuram-based crosslinking accelerator, dithiocarbamate-based crosslinking accelerator, etc. as a crosslinking aid. It is preferable.
また、架橋剤として有機過酸化物系架橋剤を使用する場合は、架橋助剤として、トリアリルシアヌレート、トリメチロールプロパントリメタクリレート、Ｎ，Ｎ’－ｍ－フェニレンビスマレイミドなどを併用することが好ましい。 In addition, when using an organic peroxide-based crosslinking agent as a crosslinking agent, triallyl cyanurate, trimethylolpropane trimethacrylate, N,N'-m-phenylene bismaleimide, etc. may be used in combination as a crosslinking aid. preferable.
また、架橋剤としてポリアミン系架橋剤を使用する場合は、架橋助剤として、下記一般式（２）で表される化合物や、環状アミジン構造を有する塩基性架橋促進剤、グアニジン系塩基性架橋促進剤、アルデヒドアミン系塩基性架橋促進剤などの塩基性架橋促進剤を併用することが好ましい。
Ｒ１－ＮＨ－Ｒ２ （２）
（上記一般式（２）中、Ｒ１およびＲ２は、それぞれ独立して、置換基を有していてもよい炭素数１～１２のアルキル基、または、置換基を有していてもよい炭素数５～１２のシクロアルキル基である。）
In addition, when using a polyamine crosslinking agent as a crosslinking agent, a compound represented by the following general formula (2), a basic crosslinking accelerator having a cyclic amidine structure, or a guanidine basic crosslinking accelerator can be used as a crosslinking agent. It is preferable to use a basic crosslinking accelerator such as an aldehyde amine type basic crosslinking accelerator.
R 1 -NH-R 2 (2)
(In the above general formula (2), R 1 and R 2 are each independently an alkyl group having 1 to 12 carbon atoms which may have a substituent or a substituent. It is a cycloalkyl group having 5 to 12 carbon atoms.)
架橋助剤は、単独で使用してもよいし、また、複数種を併用してもよく、クレー、炭酸カルシウム、シリカなどに分散させ、加工性を改良したものを使用してもよい。架橋助剤の使用量は特に限定されず、ゴム架橋物の用途、要求性能、架橋剤の種類、架橋助剤の種類などに応じて決めればよい。 The crosslinking aid may be used alone or in combination, or may be dispersed in clay, calcium carbonate, silica, etc. to improve processability. The amount of crosslinking aid used is not particularly limited, and may be determined depending on the use of the crosslinked rubber product, required performance, type of crosslinking agent, type of crosslinking aid, etc.
また、架橋物の形状、大きさなどによっては、表面が架橋していても内部まで十分に架橋していない場合があるので、さらに加熱して二次架橋を行ってもよい。
加熱方法としては、プレス加熱、スチーム加熱、オーブン加熱、熱風加熱などのゴムの架橋に用いられる一般的な方法を適宜選択すればよい。
Moreover, depending on the shape, size, etc. of the crosslinked object, even if the surface is crosslinked, the inside may not be sufficiently crosslinked, so secondary crosslinking may be performed by further heating.
As the heating method, a general method used for crosslinking rubber such as press heating, steam heating, oven heating, hot air heating, etc. may be appropriately selected.
このようにして得られる本発明のゴム架橋物は、上述した本発明のニトリルゴム組成物を架橋して得られるものであるため、低硬度でありながら、引張強度に優れるものである。 The rubber crosslinked product of the present invention thus obtained is obtained by crosslinking the above-described nitrile rubber composition of the present invention, and therefore has low hardness and excellent tensile strength.
このため、本発明のゴム架橋物は、このような特性を活かし、Ｏ－リング、パッキン、ダイアフラム、オイルシール、シャフトシール、ベアリングシール、ウェルヘッドシール、ショックアブソーバシール、ロングライフクーラント（ＬＬＣ）など冷却液の密封用シールであるクーラントシールやオイルクーラントシール、空気圧機器用シール、エアコンディショナの冷却装置や空調装置の冷凍機用コンプレッサに使用されるフロン若しくはフルオロ炭化水素または二酸化炭素の密封用シール、精密洗浄の洗浄媒体に使用される超臨界二酸化炭素または亜臨界二酸化炭素の密封用シール、転動装置（転がり軸受、自動車用ハブユニット、自動車用ウォーターポンプ、リニアガイド装置およびボールねじ等）用のシール、バルブおよびバルブシート、ＢＯＰ（Ｂｌｏｗ Ｏｕｔ Ｐｒｅｖｅｎｔｅｒ）、プラターなどの各種シール材；インテークマニホールドとシリンダヘッドとの連接部に装着されるインテークマニホールドガスケット、シリンダブロックとシリンダヘッドとの連接部に装着されるシリンダヘッドガスケット、ロッカーカバーとシリンダヘッドとの連接部に装着されるロッカーカバーガスケット、オイルパンとシリンダブロックあるいはトランスミッションケースとの連接部に装着されるオイルパンガスケット、正極、電解質板および負極を備えた単位セルを挟み込む一対のハウジング間に装着される燃料電池セパレーター用ガスケット、ハードディスクドライブのトップカバー用ガスケットなどの各種ガスケット；印刷用ロール、製鉄用ロール、製紙用ロール、工業用ロール、事務機用ロールなどの各種ロール；平ベルト（フィルムコア平ベルト、コード平ベルト、積層式平ベルト、単体式平ベルト等）、Ｖベルト（ラップドＶベルト、ローエッジＶベルト等）、Ｖリブドベルト（シングルＶリブドベルト、ダブルＶリブドベルト、ラップドＶリブドベルト、背面ゴムＶリブドベルト、上コグＶリブドベルト等）、ＣＶＴ用ベルト、タイミングベルト、歯付ベルト、コンベアーベルト、などの各種ベルト；燃料ホース、ターボエアーホース、オイルホース、ラジェターホース、ヒーターホース、ウォーターホース、バキュームブレーキホース、コントロールホース、エアコンホース、ブレーキホース、パワーステアリングホース、エアーホース、マリンホース、ライザー、フローラインなどの各種ホース；ＣＶＪブーツ、プロペラシャフトブーツ、等速ジョイントブーツ、ラックアンドピニオンブーツなどの各種ブーツ；クッション材、ダイナミックダンパ、ゴムカップリング、空気バネ、防振材、クラッチフェーシング材などの減衰材ゴム部品；ダストカバー、自動車内装部材、タイヤ、被覆ケーブル、靴底、電磁波シールド、フレキシブルプリント基板用接着剤等の接着剤、燃料電池セパレーターの他、エレクトロニクス分野など幅広い用途に使用することができる。これらの中でも、ロール、ベルト、ホースに好適に使用できる。さらにこれらの中でも、特にロールに好適である。 For this reason, the crosslinked rubber product of the present invention takes advantage of these characteristics to be used in O-rings, packings, diaphragms, oil seals, shaft seals, bearing seals, well head seals, shock absorber seals, long life coolants (LLC), etc. Coolant seals and oil coolant seals for sealing coolant, seals for pneumatic equipment, and seals for sealing fluorocarbons, fluorohydrocarbons, or carbon dioxide used in air conditioner cooling devices and refrigerator compressors of air conditioners. , seals for supercritical carbon dioxide or subcritical carbon dioxide used as cleaning media for precision cleaning, for rolling devices (rolling bearings, automotive hub units, automotive water pumps, linear guide devices, ball screws, etc.) Various sealing materials such as seals, valves and valve seats, BOP (Blow Out Preventer), platters; intake manifold gaskets installed at the joint between the intake manifold and cylinder head; installed at the joint between the cylinder block and cylinder head cylinder head gasket installed at the joint between the rocker cover and cylinder head, oil pan gasket installed at the joint between the oil pan and cylinder block or transmission case, positive electrode, electrolyte plate, and negative electrode. Various gaskets, such as gaskets for fuel cell separators and gaskets for top covers of hard disk drives, which are installed between a pair of housings that sandwich a unit cell with a built-in structure; printing rolls, rolls for steelmaking, rolls for papermaking, industrial rolls, and office machines. Various rolls such as rolls for use; flat belts (film core flat belts, cord flat belts, laminated flat belts, single-piece flat belts, etc.), V belts (wrapped V belts, raw edge V belts, etc.), V-ribbed belts (single V-ribbed belts) , double V-ribbed belts, wrapped V-ribbed belts, back rubber V-ribbed belts, upper cog V-ribbed belts, etc.), various belts such as CVT belts, timing belts, toothed belts, conveyor belts; fuel hoses, turbo air hoses, oil hoses, Various hoses such as radiator hose, heater hose, water hose, vacuum brake hose, control hose, air conditioner hose, brake hose, power steering hose, air hose, marine hose, riser, flow line; CVJ boots, propeller shaft boots, constant velocity Various types of boots such as joint boots and rack and pinion boots; Damping rubber parts such as cushioning materials, dynamic dampers, rubber couplings, air springs, vibration isolating materials, and clutch facing materials; Dust covers, automobile interior parts, tires, and coated cables It can be used in a wide range of applications, including shoe soles, electromagnetic shielding, adhesives for flexible printed circuit boards, fuel cell separators, and in the electronics field. Among these, it can be suitably used for rolls, belts, and hoses. Furthermore, among these, it is particularly suitable for rolls.
以下に、実施例および比較例を挙げて本発明を具体的に説明する。以下において、特記しない限り「部」は重量基準である。なお、試験、評価は以下によった。 The present invention will be specifically explained below with reference to Examples and Comparative Examples. In the following, "parts" are based on weight unless otherwise specified. The test and evaluation were as follows.
＜常態物性（引張強度、伸び、硬さ）＞
ニトリルゴム組成物と架橋剤を混錬して得られた架橋性ゴム組成物を、縦１５ｃｍ、横１５ｃｍ、深さ０．２ｃｍの金型に入れ、プレス圧１０ＭＰａで加圧しながら１５０℃で６０分間プレス成形してシート状のゴム架橋物を得た。次いで、得られたシート状のゴム架橋物をＪＩＳ３号形ダンベルで打ち抜いて試験片を作製した。そして、得られた試験片を用いて、ＪＩＳ Ｋ６２５１：２０１７に従い、ゴム架橋物の引張強度、および破断時の伸びをそれぞれ測定した。また、デュロメータ硬さ試験機（タイプＡ）を用いて、ＪＩＳ Ｋ６２５３－３に従い、ゴム架橋物の硬さを測定した。
<Normal physical properties (tensile strength, elongation, hardness)>
A crosslinkable rubber composition obtained by kneading a nitrile rubber composition and a crosslinking agent was placed in a mold measuring 15 cm long, 15 cm wide, and 0.2 cm deep, and heated at 150°C for 60°C while pressurizing with a press pressure of 10 MPa. A crosslinked rubber product in the form of a sheet was obtained by press molding for a minute. Next, the obtained sheet-like crosslinked rubber product was punched out using a JIS No. 3 dumbbell to prepare a test piece. Using the obtained test piece, the tensile strength and elongation at break of the rubber crosslinked material were measured in accordance with JIS K6251:2017. Further, the hardness of the crosslinked rubber product was measured using a durometer hardness tester (type A) according to JIS K6253-3.
＜実施例１＞
油展ニトリルゴム（商品名「Ｎｉｐｏｌ ＤＮ２３０」、日本ゼオン社製、アクリロニトリル単位含有量：２９重量％、アジピン酸エーテルエステル系可塑剤含有量：１７重量％）１００部に対し、ステアリン酸１部、酸化亜鉛５部、シリカ（商品名「カープレックス＃１１２０」、エボニック社製、無機充填剤）３５部、酸化チタン（商品名「TITONE A-110」、堺化学工業社製）８部、配合用可塑剤（商品名「アデカサイザー ＲＳ－１０７」、ＡＤＥＫＡ社製）２５部、シランカップリング剤（商品名「Ａ－１８９」、モメンティブ社製）０．５部、２,２,４-トリメチル-１,２-ジヒドロキノリン重合体（商品名「ノクラック２２４」、大内新興化学工業社製、老化防止剤）１部を配合して混錬した。次いで、得られた混合物を５０℃のロールに移して、粉末硫黄（３２５メッシュ）０．５部、テトラメチルチウラムジスルフィド（商品名「ノクセラーＴＴ」、大内新興化学工業社製、加硫促進剤）１．５部、Ｎ-シクロヘキシル-２-ベンゾチアゾリルスルフェンアミド（商品名「ノクセラーＣＺ」、大内新興化学工業社製、加硫促進剤）１．５部を添加して混錬した。得られた架橋性ゴム組成物を用いて、上記方法に従い、常態物性（引張強度、伸び、硬さ）の測定を行った。結果を表１に示す。
<Example 1>
1 part of stearic acid per 100 parts of oil-extended nitrile rubber (trade name "Nipol DN230", manufactured by Nippon Zeon Co., Ltd., acrylonitrile unit content: 29% by weight, adipic acid ether ester plasticizer content: 17% by weight), 5 parts of zinc oxide, 35 parts of silica (trade name "Carplex #1120", manufactured by Evonik, inorganic filler), 8 parts of titanium oxide (trade name "TITONE A-110", manufactured by Sakai Chemical Industry Co., Ltd.), for blending 25 parts of plasticizer (trade name "ADEKASIZER RS-107", manufactured by ADEKA), 0.5 part of silane coupling agent (trade name "A-189", manufactured by Momentive), 2,2,4-trimethyl- One part of 1,2-dihydroquinoline polymer (trade name "Nocrac 224", manufactured by Ouchi Shinko Kagaku Kogyo Co., Ltd., anti-aging agent) was blended and kneaded. Next, the obtained mixture was transferred to a roll at 50°C, and 0.5 parts of powdered sulfur (325 mesh) and tetramethylthiuram disulfide (trade name "Noxeler TT", manufactured by Ouchi Shinko Kagaku Kogyo Co., Ltd., vulcanization accelerator) were added. ), 1.5 parts of N-cyclohexyl-2-benzothiazolylsulfenamide (trade name "Noxela CZ", manufactured by Ouchi Shinko Kagaku Kogyo Co., Ltd., vulcanization accelerator) were added and kneaded. . Using the obtained crosslinkable rubber composition, normal state physical properties (tensile strength, elongation, hardness) were measured according to the above method. The results are shown in Table 1.
＜実施例２＞
粉末硫黄の含有量を１．５部に変更し、加硫促進剤として、１,３－ジフェニルグアニジン（商品名「ノクセラーＤ」、大内新興化学工業社製）０．２５部、およびジベンゾチアジルジスルフィド（商品名「ノクセラーＤＭ」、大内新興化学工業社製）１．５部を用いた以外は、実施例１と同様にして、ニトリルゴム組成物を得て、同様に評価を行った。結果を表１に示す。
<Example 2>
The content of powdered sulfur was changed to 1.5 parts, and 0.25 parts of 1,3-diphenylguanidine (trade name "Noxela D", manufactured by Ouchi Shinko Kagaku Kogyo Co., Ltd.) and dibenzothia were added as vulcanization accelerators. A nitrile rubber composition was obtained in the same manner as in Example 1, except that 1.5 parts of dilsulfide (trade name "Noxela DM", manufactured by Ouchi Shinko Kagaku Kogyo Co., Ltd.) was used, and evaluation was performed in the same manner. . The results are shown in Table 1.
＜比較例１＞
油展ニトリルゴム（Ｎｉｐｏｌ ＤＮ２３０）に代えて、ニトリルゴム（商品名「Ｎｉｐｏｌ ３３５０」、日本ゼオン社製、アクリロニトリル単位含有量：３３重量％、可塑剤を含有しない）を用い、配合用可塑剤の含有量を５０部に変更し、その他の配合剤の含有量を表１に記載の量に変更した以外は、実施例１と同様にしてニトリルゴム組成物を得た。そして、粉末硫黄および架橋促進剤の量を表１に記載の量に変更した以外は、実施例１と同様にして架橋性ゴム組成物を得て、同様に評価を行った。結果を表１に示す。
<Comparative example 1>
Instead of oil-extended nitrile rubber (Nipol DN230), nitrile rubber (trade name "Nipol 3350", manufactured by Nippon Zeon Co., Ltd., acrylonitrile unit content: 33% by weight, containing no plasticizer) was used, and the compounding plasticizer was A nitrile rubber composition was obtained in the same manner as in Example 1, except that the content was changed to 50 parts and the contents of other compounding ingredients were changed to the amounts listed in Table 1. A crosslinkable rubber composition was obtained in the same manner as in Example 1, except that the amounts of powdered sulfur and crosslinking accelerator were changed to those listed in Table 1, and evaluated in the same manner. The results are shown in Table 1.
＜比較例２＞
油展ニトリルゴム（Ｎｉｐｏｌ ＤＮ２３０）に代えて、ニトリルゴム（商品名「Ｎｉｐｏｌ ３３５０」、日本ゼオン社製、アクリロニトリル単位含有量：３３重量％、可塑剤を含有しない）を用い、配合用可塑剤の含有量を５０部に変更し、その他の配合剤の含有量を表１に記載の量に変更した以外は、実施例２と同様にしてニトリルゴム組成物を得た。そして、粉末硫黄および架橋促進剤の量を表１に記載の量に変更した以外は、実施例２と同様にして架橋性ゴム組成物を得て、同様に評価を行った。結果を表１に示す。
<Comparative example 2>
Instead of oil-extended nitrile rubber (Nipol DN230), nitrile rubber (trade name "Nipol 3350", manufactured by Nippon Zeon Co., Ltd., acrylonitrile unit content: 33% by weight, containing no plasticizer) was used, and the compounding plasticizer was A nitrile rubber composition was obtained in the same manner as in Example 2, except that the content was changed to 50 parts and the contents of other compounding ingredients were changed to the amounts listed in Table 1. A crosslinkable rubber composition was obtained in the same manner as in Example 2, except that the amounts of powdered sulfur and crosslinking accelerator were changed to those shown in Table 1, and evaluated in the same manner. The results are shown in Table 1.
＜実施例と比較例の評価＞
表１より、油展ニトリルゴムと、配合用可塑剤と、充填剤と、を含むニトリルゴム組成物であって、油展ニトリルゴムに含有されるゴム添加可塑剤の含有量がニトリルゴム成分１００重量部に対して１５重量部以上であるニトリルゴム組成物によれば、得られるゴム架橋物を、低硬度としながら、引張強度および伸びに優れたものとすることができた（実施例１，２）。
一方、油展ニトリルゴムに代えて、可塑剤を含有しないニトリルゴムを用いた場合は、得られるゴム架橋物の引張強度および伸びに劣る結果となった（比較例１，２）。
<Evaluation of Examples and Comparative Examples>
Table 1 shows that the nitrile rubber composition contains oil-extended nitrile rubber, a compounding plasticizer, and a filler, and the content of the rubber-added plasticizer contained in the oil-extended nitrile rubber is 100% of the nitrile rubber component. According to the nitrile rubber composition containing 15 parts by weight or more based on the weight part, the resulting rubber crosslinked product could be made to have low hardness and excellent tensile strength and elongation (Example 1, 2).
On the other hand, when a nitrile rubber containing no plasticizer was used instead of the oil-extended nitrile rubber, the result was that the resulting crosslinked rubber product had poor tensile strength and elongation (Comparative Examples 1 and 2).
＜実施例３～４９＞
表２～６に示す配合にて、ニトリルゴム組成物を得て、上記常態物性の評価と同様にして、シート状のゴム架橋物を得た。
なお、実施例３～４９においては、各表に示すニトリルゴムと、配合剤とを各表に示す量にて配合して、５０℃で混合した後、得られたニトリルゴム組成物を５０℃のロールに移して、各表に示す架橋剤・架橋促進剤を配合して混錬した。
実施例３～４９に係るニトリルゴム組成物も、油展ニトリルゴムと、配合用可塑剤と、充填剤とを含有するため、得られたゴム架橋物は、実施例１と同様に、低硬度でありながら、引張強度および伸びに優れたものであると考えられる。
<Examples 3 to 49>
Nitrile rubber compositions were obtained with the formulations shown in Tables 2 to 6, and sheet-like crosslinked rubber products were obtained in the same manner as in the evaluation of normal state physical properties.
In Examples 3 to 49, the nitrile rubber shown in each table and the compounding agent were blended in the amounts shown in each table, mixed at 50°C, and then the obtained nitrile rubber composition was heated at 50°C. The mixture was transferred to a roll, and the crosslinking agent and crosslinking accelerator shown in each table were mixed and kneaded.
Since the nitrile rubber compositions according to Examples 3 to 49 also contain oil-extended nitrile rubber, a compounding plasticizer, and a filler, the obtained crosslinked rubber products have low hardness as in Example 1. However, it is considered to have excellent tensile strength and elongation.
各表に示すゴムおよび配合剤は以下の通りである。
・Ｎｉｐｏｌ ＤＮ２３０：油展ニトリルゴム（商品名「Ｎｉｐｏｌ ＤＮ２３０」、日本ゼオン社製、アクリロニトリル単位含有量：２９重量％、アジピン酸エーテルエステル系可塑剤含有量：１７重量％）
・Ｎｉｐｏｌ ＤＮ３３５０：ニトリルゴム（商品名「Ｎｉｐｏｌ ３３５０」、日本ゼオン社製、アクリロニトリル単位含有量：３３重量％、可塑剤を含有しない）
・シースト Ｓ：カーボンブラック（商品名「シースト Ｓ」、東海カーボン社製、無機充填剤）
・シースト ＳＯ：カーボンブラック（商品名「シースト ＳＯ」、東海カーボン社製、無機充填剤）
・Ｎｉｐｓｉｌ ＶＮ３：シリカ（商品名「Ｎｉｐｓｉｌ ＶＮ３」、東ソー・シリカ社製、ＢＥＴ比表面積：２００ｍ２／ｇ）
・炭酸カルシウム（商品名「シルバーＷ」、白石カルシウム社製、無機充填剤）
・クラウンクレー：クレー（商品名「ST-CROWN」、白石カルシウム社製、無機充填剤）
・酸化チタン（商品名「TITONE A-110」、堺化学工業社製、無機充填剤）
・アデカサイザー ＲＳ－１０７：可塑剤（商品名「アデカサイザー ＲＳ－１０７」、ＡＤＥＫＡ社製）
・Ａ－１８９：シランカップリング剤（商品名「Ａ－１８９」、モメンティブ社製）
・Ａ－１７２：シランカップリング剤（商品名「Ａ－１７２」、モメンティブ社製）
・ノクラック２２４：２,２,４-トリメチル-１,２-ジヒドロキノリン重合体（商品名「ノクラック２２４」、大内新興化学工業社製、老化防止剤）
・ノクセラーＤ：１,３－ジフェニルグアニジン（商品名「ノクセラーＤ」、大内新興化学工業社製、加硫促進剤）
・ノクセラーＤＭ：ジベンゾチアジルジスルフィド（商品名「ノクセラーＤＭ」、大内新興化学工業社製、加硫促進剤）
・ノクセラーＴＴ：テトラメチルチウラムジスルフィド（商品名「ノクセラーＴＴ」、大内新興化学工業社製、加硫促進剤）１．５部
・ノクセラーＣＺ：Ｎ-シクロヘキシル-２-ベンゾチアゾリルスルフェンアミド（商品名「ノクセラーＣＺ」、大内新興化学工業社製、加硫促進剤）
・パークミルＤ－４０：ジクミルペルオキシド（商品名「パークミルＤ－４０」、日油社製、過酸化物架橋剤）
・ＴＭＰＴ：トリメチロールプロパントリメタクリレート（商品名「ＴＭＰＴ」、新中村化学社製、架橋助剤）
The rubbers and compounding agents shown in each table are as follows.
・Nipol DN230: Oil-extended nitrile rubber (trade name "Nipol DN230", manufactured by Nippon Zeon Co., Ltd., acrylonitrile unit content: 29% by weight, adipic acid ether ester plasticizer content: 17% by weight)
・Nipol DN3350: Nitrile rubber (trade name "Nipol 3350", manufactured by Nippon Zeon Co., Ltd., acrylonitrile unit content: 33% by weight, does not contain plasticizer)
・SEAST S: Carbon black (product name "SEAST S", manufactured by Tokai Carbon Co., Ltd., inorganic filler)
・SEAST SO: Carbon black (product name "SEAST SO", manufactured by Tokai Carbon Co., Ltd., inorganic filler)
・Nipsil VN3: Silica (product name "Nipsil VN3", manufactured by Tosoh Silica Co., Ltd., BET specific surface area: 200 m 2 /g)
・Calcium carbonate (product name "Silver W", manufactured by Shiraishi Calcium Co., Ltd., inorganic filler)
・Crown clay: Clay (product name "ST-CROWN", manufactured by Shiraishi Calcium Co., Ltd., inorganic filler)
・Titanium oxide (trade name "TITONE A-110", manufactured by Sakai Chemical Industry Co., Ltd., inorganic filler)
・ADEKASIZER RS-107: Plasticizer (product name: ADEKASIZER RS-107, manufactured by ADEKA)
・A-189: Silane coupling agent (trade name "A-189", manufactured by Momentive)
・A-172: Silane coupling agent (trade name "A-172", manufactured by Momentive)
・Nocrac 224: 2,2,4-trimethyl-1,2-dihydroquinoline polymer (trade name "Nocrac 224", manufactured by Ouchi Shinko Kagaku Kogyo Co., Ltd., anti-aging agent)
・Noccela D: 1,3-diphenylguanidine (trade name "Noccellar D", manufactured by Ouchi Shinko Kagaku Kogyo Co., Ltd., vulcanization accelerator)
・Noccerar DM: Dibenzothiazyl disulfide (trade name "Noccerer DM", manufactured by Ouchi Shinko Kagaku Kogyo Co., Ltd., vulcanization accelerator)
・Noccela TT: 1.5 parts of tetramethylthiuram disulfide (trade name "Noccella TT", manufactured by Ouchi Shinko Kagaku Kogyo Co., Ltd., vulcanization accelerator) ・Noccellar CZ: N-cyclohexyl-2-benzothiazolylsulfenamide ( Product name: “Noxeler CZ”, manufactured by Ouchi Shinko Kagaku Kogyo Co., Ltd., vulcanization accelerator)
・Percyl D-40: dicumyl peroxide (trade name "Percyl D-40", manufactured by NOF Corporation, peroxide crosslinking agent)
・TMPT: Trimethylolpropane trimethacrylate (trade name "TMPT", manufactured by Shin Nakamura Chemical Co., Ltd., crosslinking aid)
Claims (5)
前記油展ニトリルゴムは、ニトリルゴム成分と、ゴム添加可塑剤とを含み、
前記油展ニトリルゴムにおける前記ゴム添加可塑剤の含有割合が、前記油展ニトリルゴム中の前記ニトリルゴム成分１００重量部に対して１５重量部以上であるニトリルゴム組成物。 A nitrile rubber composition comprising an oil-extended nitrile rubber, a compounding plasticizer, and a filler,
The oil-extended nitrile rubber includes a nitrile rubber component and a rubber-added plasticizer,
A nitrile rubber composition, wherein the content of the rubber-added plasticizer in the oil-extended nitrile rubber is 15 parts by weight or more based on 100 parts by weight of the nitrile rubber component in the oil-extended nitrile rubber.
デュロメータ硬さ試験により測定される硬さが５０以下であるゴム架橋物。 A crosslinked rubber product obtained by crosslinking the nitrile rubber composition according to any one of claims 1 to 4,
A crosslinked rubber product having a hardness of 50 or less as measured by a durometer hardness test.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022028991A JP2023125069A (en) | 2022-02-28 | 2022-02-28 | Nitrile rubber composition and rubber crosslinked product |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022028991A JP2023125069A (en) | 2022-02-28 | 2022-02-28 | Nitrile rubber composition and rubber crosslinked product |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2023125069A true JP2023125069A (en) | 2023-09-07 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022028991A Pending JP2023125069A (en) | 2022-02-28 | 2022-02-28 | Nitrile rubber composition and rubber crosslinked product |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2023125069A (en) |
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2022
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