JP5712317B2 - 官能基化高ビニルジエンゴム - Google Patents
官能基化高ビニルジエンゴム Download PDFInfo
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- JP5712317B2 JP5712317B2 JP2014104115A JP2014104115A JP5712317B2 JP 5712317 B2 JP5712317 B2 JP 5712317B2 JP 2014104115 A JP2014104115 A JP 2014104115A JP 2014104115 A JP2014104115 A JP 2014104115A JP 5712317 B2 JP5712317 B2 JP 5712317B2
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- Prior art keywords
- rubber
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- 229920002554 vinyl polymer Polymers 0.000 title claims description 27
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title claims description 24
- 229920003244 diene elastomer Polymers 0.000 title description 8
- 229920001971 elastomer Polymers 0.000 claims description 100
- 239000005060 rubber Substances 0.000 claims description 99
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- 238000000034 method Methods 0.000 claims description 23
- 239000000945 filler Substances 0.000 claims description 21
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 17
- 125000000524 functional group Chemical group 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- 150000001993 dienes Chemical class 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical compound OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 claims description 7
- 239000003999 initiator Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
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- 239000001301 oxygen Substances 0.000 claims description 5
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- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
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- 150000003254 radicals Chemical class 0.000 claims description 4
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical compound SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910021645 metal ion Chemical group 0.000 claims description 2
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- 238000006116 polymerization reaction Methods 0.000 description 8
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- 229910052725 zinc Inorganic materials 0.000 description 7
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- 239000000377 silicon dioxide Substances 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
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- 238000004566 IR spectroscopy Methods 0.000 description 4
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- 229910052791 calcium Inorganic materials 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- NUNQKTCKURIZQX-UHFFFAOYSA-N 2-(2-ethoxyethoxy)-2-methylpropane Chemical compound CCOCCOC(C)(C)C NUNQKTCKURIZQX-UHFFFAOYSA-N 0.000 description 3
- GAODDBNJCKQQDY-UHFFFAOYSA-N 2-methyl-4,6-bis(octylsulfanylmethyl)phenol Chemical compound CCCCCCCCSCC1=CC(C)=C(O)C(CSCCCCCCCC)=C1 GAODDBNJCKQQDY-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- 244000043261 Hevea brasiliensis Species 0.000 description 3
- 239000002174 Styrene-butadiene Substances 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012967 coordination catalyst Substances 0.000 description 3
- 239000010419 fine particle Substances 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 229920003052 natural elastomer Polymers 0.000 description 3
- 229920001194 natural rubber Polymers 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
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- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- QRMPKOFEUHIBNM-UHFFFAOYSA-N 1,4-dimethylcyclohexane Chemical compound CC1CCC(C)CC1 QRMPKOFEUHIBNM-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
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- QNNVICQPXUUBSN-UHFFFAOYSA-N 2-sulfanylpropan-1-ol Chemical compound CC(S)CO QNNVICQPXUUBSN-UHFFFAOYSA-N 0.000 description 2
- SHLSSLVZXJBVHE-UHFFFAOYSA-N 3-sulfanylpropan-1-ol Chemical compound OCCCS SHLSSLVZXJBVHE-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- 229920002943 EPDM rubber Polymers 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229910052779 Neodymium Inorganic materials 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 2
- 150000001733 carboxylic acid esters Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
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- 230000003993 interaction Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000010068 moulding (rubber) Methods 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
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- 150000002978 peroxides Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- 239000011591 potassium Substances 0.000 description 2
- 239000011164 primary particle Substances 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
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- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
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- IRKZIGMIBWVNOU-UHFFFAOYSA-N 1-sulfanyldecan-1-ol Chemical compound CCCCCCCCCC(O)S IRKZIGMIBWVNOU-UHFFFAOYSA-N 0.000 description 1
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- PSMXCVLAHHLSIF-UHFFFAOYSA-N 1-sulfanyloctadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCC(O)S PSMXCVLAHHLSIF-UHFFFAOYSA-N 0.000 description 1
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- KBNXPWYPEFJHSF-UHFFFAOYSA-N 2-hydroxypropanethioic S-acid 2-sulfanylpropanoic acid Chemical compound C(C(O)C)(=S)O.SC(C(=O)O)C KBNXPWYPEFJHSF-UHFFFAOYSA-N 0.000 description 1
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- REFZTFPICLNNPM-UHFFFAOYSA-N 2-sulfanyldodecanoic acid Chemical compound CCCCCCCCCCC(S)C(O)=O REFZTFPICLNNPM-UHFFFAOYSA-N 0.000 description 1
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- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 1
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- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
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- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000003857 carboxamides Chemical group 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
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- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical class NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 1
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- 230000006866 deterioration Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-O diethylammonium Chemical compound CC[NH2+]CC HPNMFZURTQLUMO-UHFFFAOYSA-O 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-O ethylaminium Chemical compound CC[NH3+] QUSNBJAOOMFDIB-UHFFFAOYSA-O 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000006232 furnace black Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 229920006168 hydrated nitrile rubber Polymers 0.000 description 1
- 238000006197 hydroboration reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 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 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000011325 microbead Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000010058 rubber compounding Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000006234 thermal black Substances 0.000 description 1
- RSPCKAHMRANGJZ-UHFFFAOYSA-N thiohydroxylamine Chemical class SN RSPCKAHMRANGJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0016—Compositions of the tread
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/20—Incorporating sulfur atoms into the molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
- C08C19/42—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups
- C08C19/44—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups of polymers containing metal atoms exclusively at one or both ends of the skeleton
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
- Y02T10/00—Road transport of goods or passengers
- Y02T10/80—Technologies aiming to reduce greenhouse gasses emissions common to all road transportation technologies
- Y02T10/86—Optimisation of rolling resistance, e.g. weight reduction
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Tires In General (AREA)
Description
HS−R1−COOXまたは(HS−R1−COO)2X
(式中、
R1は、それぞれが、必要に応じて、3個以下のさらなるカルボキシ基を置換基として有することができるか、または窒素原子、酸素原子もしくは硫黄原子によって中断されることができる、線状、分岐もしくは環状のC1〜C36アルキレン基もしくはC1〜C36アルケニレン基であるか、またはアリール基であり、
Xは、水素または金属イオン、例えばLi、Na、K、Mg、Zn、Caまたは、必要に応じて、置換基としてC1〜C36アルキル基、C1〜C36アルケニル基、シクロアルキル基もしくはアリール基を有するアンモニウムイオンである)
のカルボキシメルカプタンとの、必要に応じてフリーラジカル開始剤の存在下での、得られたポリマーの反応によって溶液中で行われる。
HS−R2−OH
(式中、
R2は、それぞれが、必要に応じて、3個以下のさらなるヒドロキシ基を置換基として有することができるか、または窒素原子、酸素原子もしくは硫黄原子によって中断されることができるか、またはアリール置換基を有することができる、線状、分岐もしくは環状のC1〜C36アルキレン基もしくはC1〜C36アルケニレン基であるか、またはアリール基である)
のヒドロキシメルカプタンとの、必要に応じてフリーラジカル開始剤の存在下での、得られたポリマーの反応によって溶液中で行われる。
HS−R3−COOR4、HS−R3−NR5R6
(式中、
R3は、それぞれが、必要に応じて、3個以下のさらなるカルボン酸エステル基もしくはアミノ基を置換基として有することができるか、または窒素原子、酸素原子もしくは硫黄原子によって中断されることができる、線状、分岐もしくは環状のC1〜C36アルキレン基もしくはC1〜C36アルケニレン基であるか、またはアリール基であり、
R4は、必要に応じて、窒素原子、酸素原子もしくは硫黄原子によって中断されることができる線状、分岐もしくは環状のC1〜C36アルキル基もしくはC1〜C36アルケニル基であるか、または5個以下のアルキル置換基もしくは芳香族置換基を有することができるフェニル基であり、
R5およびR6は、水素、または、必要に応じて、窒素原子、酸素原子もしくは硫黄原子によって中断されることができる線状、分岐もしくは環状のC1〜C36アルキル基もしくはC1〜C36アルケニル基であるか、または5個以下のアルキル置換基もしくは芳香族置換基を有することができるフェニル基である)
のメルカプトカルボン酸エステルおよびメルカプトアミンから相当する方法で導入することができる。
− 5〜1000m2/g、好ましくは20〜400m2/gの比表面積(BET表面積)の、および10〜400nmの一次粒径の、例えば、シリケートの溶液の沈澱、またはハロゲン化ケイ素の火炎加水分解によって製造された、微細粒子シリカ。シリカはまた、必要に応じて、Al、Mg、Ca、Ba、Zn、Zr、またはTi酸化物などの、他の金属酸化物との混合酸化物の形態で存在することができる;
− 20〜400m2/gのBET表面積および10〜400nmの一次粒径の、ケイ酸アルミニウムなどの、合成シリケート、ケイ酸マグネシウムまたはケイ酸カルシウムなどの、アルカリ土類金属シリケート;
− カオリンおよび他の天然産型のシリカなどの、天然シリケート;
− ガラス繊維およびガラス繊維製品(マット、より糸)またはガラスマイクロビーズ;
− 酸化亜鉛、酸化カルシウム、酸化マグネシウム、または酸化アルミニウムなどの、金属酸化物;
− 炭酸マグネシウム、炭酸カルシウム、または炭酸亜鉛などの、金属炭酸塩;
− 水酸化アルミニウムまたは水酸化マグネシウムなどの、金属水酸化物;
− カーボンブラック:本明細書で使用されるべきカーボンブラックは、火炎−ブラック法、チャンネル−ブラック法、ファーネス−ブラック法、ガス−ブラック法、サーマル−ブラック法、アセチレン−ブラック法またはアーク法によって製造されたカーボンブラックであり、それらのBET表面積は9〜200m2/gであり、例えばSAF、ISAF−LS、ISAF−HM、ISAF−LM、ISAF−HS、CF、SCF、HAF−LS、HAF、HAF−HS、FF−HS、SRF、XCF、FEF−LS、FEF、FEF−HS、GPF−HS、GPF、APF、SRF−LS、SRF−LM、SRF−HS、SRF−HMおよびMTカーボンブラック、ASTMによるN110、N219、N220、N231、N234、N242、N294、N326、N327、N330、N332、N339、N347、N351、N356、N358、N375、N472、N539、N550、N568、N650、N660、N754、N762、N765、N774、N787およびN990カーボンブラック;
− ゴムゲル、特にポリブタジエン、ブタジエン−スチレンコポリマー、ブタジエン−アクリロニトリルコポリマーおよびポリクロロプレンをベースとするもの
が挙げられる。
BR=ポリブタジエン
ABR=ブタジエン/C1〜C4アルキルアクリレートコポリマー
CR=ポリクロロプレン
IR=ポリイソプレン
SBR=1〜60重量%、好ましくは20〜50重量%のスチレン含有率のスチレン−ブタジエンコポリマー
IIR=イソブチレン−イソプレンコポリマー
NBR=5〜60重量%、好ましくは10〜40重量%のアクリロニトリル含有率のブタジエン−アクリロニトリルコポリマー
HNBR=部分水素化または完全水素化NBRゴム
EPDM=エチレン−プロピレン−ジエンターポリマー
およびこれらのゴムの混合物を包含する。自動車タイヤの製造のために、特に対象となる材料は、天然ゴム、そのガラス転移温度が−50℃より高いエマルジョンSBRおよび溶液SBR、Ni、Co、TiまたはNdをベースとする触媒を使用して製造された高シス含有率(90%より高い)のポリブタジエンゴム、および80%以下のビニル含有率のポリブタジエンゴム、ならびにそれらの混合物である。
8.5kgのヘキサン、171ミリモルの第三ブトキシエトキシエタン、8ミリモルのブチルリチウムおよび1.5kg(27.73モル)の1,3−ブタジエンを不活性化20L反応器に装入し、内容物を80℃に加熱した。混合物を、撹拌しながら、80℃で1時間重合させた。ゴム溶液を次に排出させ、3gのIrganox 1520(登録商標)(Ciba製の2,4−ビス(オクチルチオメチル)−6−メチルフェノール)を添加することによって安定化させ、溶媒を水蒸気でストリッピングすることによって除去した。ゴム小片を真空で、65℃で乾燥させた。
実施例2:
8.5kgのヘキサン、171ミリモルの第三ブトキシエトキシエタン、10ミリモルのブチルリチウムおよび1.5kg(27.73モル)の1,3−ブタジエンを不活性化20L反応器に装入し、内容物を80℃に加熱した。混合物を、撹拌しながら80℃で1時間重合させた。21g(0.2モル)の3−メルカプトプロピオン酸および0.75gのジラウロイルペルオキシドを次に加え、反応器内容物を90℃に90分間加熱した。ゴム溶液を次に排出させ、3gのIrganox 1520(登録商標)を添加することによって安定化させ、溶媒を水蒸気でストリッピングすることによって除去した。ゴム小片を真空で、65℃で乾燥させた。
手順は実施例2の通りであった。
手順は、実施例2の通りであった。重合反応は9.5ミリモルのブチルリチウムを使用した。
実施例2〜4の官能基化高ビニル含有率ポリブタジエンならびに、比較として、実施例1に由来する非官能基化高ビニル含有率ポリブタジエンおよび市販のスチレン−ブタジエンコポリマー(Lanxess製のVSL 5025−0 HM、50%ビニル含有率、25%スチレン含有率、ムーニー粘度65、ガラス転移温度(DSC)−22℃)を含むゴム混合物を製造した。混合物成分を表1にリストする。混合物(硫黄および促進剤なし)を1.5L混練機で製造した。混合物成分硫黄および促進剤を次に40℃で、ミルで混合した。
Claims (3)
- 1種以上のジエンを溶液で重合して溶液ゴムを得る工程と、
カルボキシ基もしくはヒドロキシ基の官能基またはそれらの塩を次に前記溶液ゴム中へフリーラジカル開始剤の存在下で導入してゴムを調製する工程と、
溶媒を、真空又は非真空で、50〜200℃の温度の熱水および/または水蒸気を使用して除去する工程と、
次にフィラーを、ゴムの100重量部を基準として、10〜500重量部添加し、且つ、プロセスオイルを添加するか、またはしない工程を含むゴム混合物の製造方法であって、
使用される溶液ゴムの重量をそれぞれ基準として、前記ゴムが0.02〜3重量%の結合した官能基もしくはそれらの塩を有し、1,2−結合ジエンの含有率(ビニル含有率)が60〜95重量%であり、前記ゴムがスチレン−ブタジエンコポリマーを含まず、
前記カルボキシ基の導入が、式:
HS−R1−COOXまたは(HS−R1−COO)2X
(式中、
R1は、それぞれが、3個以下のさらなるカルボキシ基を置換基として有することができるか、または窒素原子、酸素原子もしくは硫黄原子によって中断されることができる、線状、分岐もしくは環状のC1〜C36アルキレン基もしくはC1〜C36アルケニレン基であるか、またはアリール基であり、
Xは、水素または金属イオン、または、置換基としてC1〜C36アルキル基、C1〜C36アルケニル基、シクロアルキル基もしくはアリール基を有することができるアンモニウムイオンである)
のカルボキシメルカプタンを用いて行われ、
前記ヒドロキシ基の導入が、式:
HS−R2−OH
(式中、R2は、それぞれが、3個以下のさらなるヒドロキシ基を置換基として有することができるか、または窒素原子、酸素原子もしくは硫黄原子によって中断されることができるか、またはアリール置換基を有することができる、線状、分岐もしくは環状のC1〜C36アルキレン基もしくはC1〜C36アルケニレン基であるか、またはアリール基である)
のヒドロキシメルカプタンを用いて行われ、
前記塩の導入が、前記ゴムに導入された前記官能基の中和により行われる、方法。 - 前記ジエンが1,3−ブタジエンであることを特徴とする、請求項1に記載の方法。
- 前記フィラーが、異なるフィラーの混合物であることを特徴とする、請求項1に記載の方法。
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DE (1) | DE102007044175A1 (ja) |
RU (1) | RU2491307C9 (ja) |
TW (1) | TWI485194B (ja) |
WO (1) | WO2009034001A1 (ja) |
ZA (1) | ZA201001650B (ja) |
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DE102008023885A1 (de) * | 2008-05-16 | 2009-11-19 | Lanxess Deutschland Gmbh | Funktionalisierte hochvinylaromaten-haltige Dienkautschuke |
DE102008052057A1 (de) * | 2008-10-16 | 2010-04-22 | Lanxess Deutschland Gmbh | Funktionalisierte Dienkautschuke |
US20130345335A1 (en) * | 2011-02-09 | 2013-12-26 | Jsr Corporation | Rubber composition, method for producing same, and tire |
FR2980205B1 (fr) | 2011-09-19 | 2013-09-27 | Michelin Soc Tech | Bande de roulement de pneumatique hors la route |
JP6134810B2 (ja) * | 2012-12-18 | 2017-05-24 | コンパニー ゼネラール デ エタブリッスマン ミシュラン | 官能基種のゴムへのグラフト化 |
EP2796485A1 (de) | 2013-04-24 | 2014-10-29 | LANXESS Deutschland GmbH | Cold Flow reduzierte Polymere mit gutem Verarbeitungsverhalten |
EP2796471A1 (de) | 2013-04-24 | 2014-10-29 | LANXESS Deutschland GmbH | Silanhaltige carboxyterminierte Polymere |
EP2865540A1 (de) * | 2013-10-24 | 2015-04-29 | LANXESS Deutschland GmbH | Kautschukzusammensetzung |
ITRM20130706A1 (it) * | 2013-12-20 | 2015-06-21 | Bridgestone Corp | Mescola in gomma per la preparazione di pneumatici |
CN108350182B (zh) * | 2015-10-27 | 2021-12-07 | 住友橡胶工业株式会社 | 轮胎用橡胶组合物的制造方法和轮胎制造方法 |
MX2022000632A (es) | 2019-07-16 | 2022-03-11 | Arlanxeo Deutschland Gmbh | Cauchos de dieno terminados en carboxi. |
JP6988862B2 (ja) * | 2019-08-08 | 2022-01-05 | 住友ゴム工業株式会社 | タイヤ用ゴム組成物及びタイヤ |
US11560462B1 (en) * | 2019-09-20 | 2023-01-24 | The Goodyear Tire & Rubber Company | Functionalized high cis-1,4-polybutadiene |
JP7500952B2 (ja) * | 2019-11-06 | 2024-06-18 | 住友ゴム工業株式会社 | タイヤ用ゴム組成物およびタイヤ |
WO2021220831A1 (ja) * | 2020-04-30 | 2021-11-04 | 株式会社ブリヂストン | ゴム組成物およびゴム製品 |
WO2023025878A1 (en) | 2021-08-27 | 2023-03-02 | Arlanxeo Deutschland Gmbh | Stabilized polymer compositions comprising organic acids and diene rubbers functionalized with units comprising carboxylic acid groups |
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JPH0621189B2 (ja) * | 1985-08-30 | 1994-03-23 | 日本エラストマ−株式会社 | 改善されたタイヤ用共役ジエン系ゴム組成物 |
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US6057397A (en) * | 1995-01-23 | 2000-05-02 | Nippon Zeon Co., Ltd. | Rubber composition and process for preparing the same |
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DE59907363D1 (de) * | 1998-11-16 | 2003-11-20 | Bayer Ag | Carboxylgruppen-haltige Lösungskautschuke enthaltende Kautschukmischungen |
DE19920894A1 (de) | 1999-05-06 | 2000-11-09 | Bayer Ag | Hydroxylgruppenhaltige Dienkautschuke |
DE19920788A1 (de) | 1999-05-06 | 2000-11-09 | Bayer Ag | Carboxylgruppen-haltige Dienkautschuke |
DE19956118A1 (de) * | 1999-11-22 | 2001-05-23 | Bayer Ag | Kautschukmischungen aus hydroxyl- und carboxylgruppenhaltigen Dienkautschuken und schwefelfreien Vernetzern |
DE19961522A1 (de) * | 1999-12-20 | 2001-06-21 | Bayer Ag | Lösungskautschuke mit unpolaren Seitengruppen |
US7074869B2 (en) | 2002-12-27 | 2006-07-11 | The Goodyear Tire & Rubber Company | Synthesis of functionalized high vinyl rubber |
FR2854404B1 (fr) * | 2003-04-29 | 2005-07-01 | Michelin Soc Tech | Procede d'obtention d'un elastomere greffe a groupes fonctionnels le long de la chaine et compositions de caoutchouc |
RU2260600C1 (ru) * | 2004-04-29 | 2005-09-20 | ОАО "Воронежсинтезкаучук" | Способ получения полимеров |
MX2009006746A (es) * | 2006-12-19 | 2009-08-28 | Dow Global Technologies Inc | Polimeros elastomericos modificados con sulfuro. |
US8071682B2 (en) * | 2007-06-27 | 2011-12-06 | Sumitomo Chemical Company, Limited | Method for producing conjugated diene polymer, conjugated diene polymer, and polymer composition |
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2007
- 2007-09-15 DE DE102007044175A patent/DE102007044175A1/de not_active Withdrawn
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2008
- 2008-09-04 RU RU2010114817/05A patent/RU2491307C9/ru active
- 2008-09-04 WO PCT/EP2008/061665 patent/WO2009034001A1/de active Application Filing
- 2008-09-04 KR KR1020107008112A patent/KR101162436B1/ko active IP Right Grant
- 2008-09-04 US US12/676,640 patent/US20110003932A1/en not_active Abandoned
- 2008-09-04 EP EP08803635A patent/EP2193166A1/de not_active Ceased
- 2008-09-04 CN CN2008801114426A patent/CN101821328B/zh not_active Expired - Fee Related
- 2008-09-04 JP JP2010524461A patent/JP5647894B2/ja not_active Expired - Fee Related
- 2008-09-04 BR BRPI0817066 patent/BRPI0817066A2/pt not_active Application Discontinuation
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Also Published As
Publication number | Publication date |
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CN101821328A (zh) | 2010-09-01 |
TWI485194B (zh) | 2015-05-21 |
TW200932819A (en) | 2009-08-01 |
ZA201001650B (en) | 2011-05-25 |
KR20100066565A (ko) | 2010-06-17 |
CN101821328B (zh) | 2013-03-20 |
WO2009034001A1 (de) | 2009-03-19 |
US20130281609A1 (en) | 2013-10-24 |
RU2491307C9 (ru) | 2014-04-10 |
RU2491307C2 (ru) | 2013-08-27 |
EP2193166A1 (de) | 2010-06-09 |
RU2010114817A (ru) | 2011-10-20 |
BRPI0817066A2 (pt) | 2015-03-24 |
JP5647894B2 (ja) | 2015-01-07 |
JP2010539269A (ja) | 2010-12-16 |
US20110003932A1 (en) | 2011-01-06 |
JP2014148687A (ja) | 2014-08-21 |
KR101162436B1 (ko) | 2012-07-13 |
DE102007044175A1 (de) | 2009-03-19 |
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