DE102005047115A1 - Vernetzbare Zusammensetzungen, Verfahren zu deren Herstellung und deren Verwendung - Google Patents
Vernetzbare Zusammensetzungen, Verfahren zu deren Herstellung und deren Verwendung Download PDFInfo
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- DE102005047115A1 DE102005047115A1 DE102005047115A DE102005047115A DE102005047115A1 DE 102005047115 A1 DE102005047115 A1 DE 102005047115A1 DE 102005047115 A DE102005047115 A DE 102005047115A DE 102005047115 A DE102005047115 A DE 102005047115A DE 102005047115 A1 DE102005047115 A1 DE 102005047115A1
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- Prior art keywords
- amplitude
- tert
- butyl
- elastomers
- complex viscosity
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 151
- 238000000034 method Methods 0.000 title claims abstract description 47
- 230000008569 process Effects 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title claims description 6
- 229920001971 elastomer Polymers 0.000 claims abstract description 133
- 239000000806 elastomer Substances 0.000 claims abstract description 93
- 150000007942 carboxylates Chemical class 0.000 claims abstract description 52
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 40
- 239000005060 rubber Substances 0.000 claims abstract description 40
- 230000008859 change Effects 0.000 claims abstract description 33
- 230000001419 dependent effect Effects 0.000 claims abstract description 31
- 150000003254 radicals Chemical class 0.000 claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 claims abstract description 22
- 229910052751 metal Inorganic materials 0.000 claims abstract description 20
- 239000002184 metal Substances 0.000 claims abstract description 20
- 239000004971 Cross linker Substances 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 229920000459 Nitrile rubber Polymers 0.000 claims description 35
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 35
- -1 2-ethylhexyl Chemical group 0.000 claims description 34
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 34
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 28
- 239000000178 monomer Substances 0.000 claims description 25
- 229920000642 polymer Polymers 0.000 claims description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 17
- 239000001530 fumaric acid Substances 0.000 claims description 16
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 15
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 15
- 239000011976 maleic acid Substances 0.000 claims description 15
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 14
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 14
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
- 230000001070 adhesive effect Effects 0.000 claims description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 12
- 239000000853 adhesive Substances 0.000 claims description 12
- 150000002825 nitriles Chemical class 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- 150000001993 dienes Chemical class 0.000 claims description 10
- 229920006168 hydrated nitrile rubber Polymers 0.000 claims description 10
- 238000005984 hydrogenation reaction Methods 0.000 claims description 10
- 239000003921 oil Substances 0.000 claims description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims description 6
- 239000004014 plasticizer Substances 0.000 claims description 6
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 claims description 6
- 150000001540 azides Chemical class 0.000 claims description 5
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 5
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 claims description 4
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 claims description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 4
- 229960002130 benzoin Drugs 0.000 claims description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 4
- 150000002978 peroxides Chemical class 0.000 claims description 4
- 239000012966 redox initiator Substances 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 claims description 4
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 0.000 claims description 4
- 229920006342 thermoplastic vulcanizate Polymers 0.000 claims description 4
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 claims description 4
- MVELOSYXCOVILT-UHFFFAOYSA-N (4-hydroxy-2-methylpentan-2-yl) 7,7-dimethyloctaneperoxoate Chemical compound CC(O)CC(C)(C)OOC(=O)CCCCCC(C)(C)C MVELOSYXCOVILT-UHFFFAOYSA-N 0.000 claims description 3
- XYFRHHAYSXIKGH-UHFFFAOYSA-N 3-(5-methoxy-2-methoxycarbonyl-1h-indol-3-yl)prop-2-enoic acid Chemical compound C1=C(OC)C=C2C(C=CC(O)=O)=C(C(=O)OC)NC2=C1 XYFRHHAYSXIKGH-UHFFFAOYSA-N 0.000 claims description 3
- 229920002943 EPDM rubber Polymers 0.000 claims description 3
- 229920000181 Ethylene propylene rubber Polymers 0.000 claims description 3
- 239000006057 Non-nutritive feed additive Substances 0.000 claims description 3
- 239000005062 Polybutadiene Substances 0.000 claims description 3
- 239000002174 Styrene-butadiene Substances 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 239000000539 dimer Substances 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 claims description 3
- 239000013638 trimer Substances 0.000 claims description 3
- 239000012936 vulcanization activator Substances 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 claims description 2
- HGXJDMCMYLEZMJ-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOOC(=O)C(C)(C)C HGXJDMCMYLEZMJ-UHFFFAOYSA-N 0.000 claims description 2
- OXYKVVLTXXXVRT-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzenecarboperoxoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1 OXYKVVLTXXXVRT-UHFFFAOYSA-N 0.000 claims description 2
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 claims description 2
- PYOLJOJPIPCRDP-UHFFFAOYSA-N 1,1,3-trimethylcyclohexane Chemical compound CC1CCCC(C)(C)C1 PYOLJOJPIPCRDP-UHFFFAOYSA-N 0.000 claims description 2
- IMYCVFRTNVMHAD-UHFFFAOYSA-N 1,1-bis(2-methylbutan-2-ylperoxy)cyclohexane Chemical compound CCC(C)(C)OOC1(OOC(C)(C)CC)CCCCC1 IMYCVFRTNVMHAD-UHFFFAOYSA-N 0.000 claims description 2
- HSLFISVKRDQEBY-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)cyclohexane Chemical compound CC(C)(C)OOC1(OOC(C)(C)C)CCCCC1 HSLFISVKRDQEBY-UHFFFAOYSA-N 0.000 claims description 2
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 claims description 2
- ILBBNQMSDGAAPF-UHFFFAOYSA-N 1-(6-hydroxy-6-methylcyclohexa-2,4-dien-1-yl)propan-1-one Chemical compound CCC(=O)C1C=CC=CC1(C)O ILBBNQMSDGAAPF-UHFFFAOYSA-N 0.000 claims description 2
- VVNBGZDWBJZDDA-UHFFFAOYSA-N 1-azido-4-(4-azidophenyl)-5,6-disulfonylcyclohexa-1,3-diene Chemical group N(=[N+]=[N-])C=1C(C(C(=CC=1)C1=CC=C(C=C1)N=[N+]=[N-])=S(=O)=O)=S(=O)=O VVNBGZDWBJZDDA-UHFFFAOYSA-N 0.000 claims description 2
- HQOVXPHOJANJBR-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)butane Chemical compound CC(C)(C)OOC(C)(CC)OOC(C)(C)C HQOVXPHOJANJBR-UHFFFAOYSA-N 0.000 claims description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 claims description 2
- JGBAASVQPMTVHO-UHFFFAOYSA-N 2,5-dihydroperoxy-2,5-dimethylhexane Chemical compound OOC(C)(C)CCC(C)(C)OO JGBAASVQPMTVHO-UHFFFAOYSA-N 0.000 claims description 2
- UZNOMHUYXSAUPB-UHFFFAOYSA-N 2,6-bis[(4-azidophenyl)methylidene]cyclohexan-1-one Chemical compound C1=CC(N=[N+]=[N-])=CC=C1C=C(CCC1)C(=O)C1=CC1=CC=C(N=[N+]=[N-])C=C1 UZNOMHUYXSAUPB-UHFFFAOYSA-N 0.000 claims description 2
- YKTNISGZEGZHIS-UHFFFAOYSA-N 2-$l^{1}-oxidanyloxy-2-methylpropane Chemical group CC(C)(C)O[O] YKTNISGZEGZHIS-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- DZZAHLOABNWIFA-UHFFFAOYSA-N 2-butoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCC)C(=O)C1=CC=CC=C1 DZZAHLOABNWIFA-UHFFFAOYSA-N 0.000 claims description 2
- KRDXTHSSNCTAGY-UHFFFAOYSA-N 2-cyclohexylpyrrolidine Chemical compound C1CCNC1C1CCCCC1 KRDXTHSSNCTAGY-UHFFFAOYSA-N 0.000 claims description 2
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 claims description 2
- ZACVGCNKGYYQHA-UHFFFAOYSA-N 2-ethylhexoxycarbonyloxy 2-ethylhexyl carbonate Chemical class CCCCC(CC)COC(=O)OOC(=O)OCC(CC)CCCC ZACVGCNKGYYQHA-UHFFFAOYSA-N 0.000 claims description 2
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 claims description 2
- XRXANEMIFVRKLN-UHFFFAOYSA-N 2-hydroperoxy-2-methylbutane Chemical compound CCC(C)(C)OO XRXANEMIFVRKLN-UHFFFAOYSA-N 0.000 claims description 2
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 claims description 2
- AQKYLAIZOGOPAW-UHFFFAOYSA-N 2-methylbutan-2-yl 2,2-dimethylpropaneperoxoate Chemical compound CCC(C)(C)OOC(=O)C(C)(C)C AQKYLAIZOGOPAW-UHFFFAOYSA-N 0.000 claims description 2
- MNYLCGIJDZPKLE-UHFFFAOYSA-N 2-methylbutan-2-yloxy butaneperoxoate Chemical compound CCCC(=O)OOOC(C)(C)CC MNYLCGIJDZPKLE-UHFFFAOYSA-N 0.000 claims description 2
- KFGFVPMRLOQXNB-UHFFFAOYSA-N 3,5,5-trimethylhexanoyl 3,5,5-trimethylhexaneperoxoate Chemical compound CC(C)(C)CC(C)CC(=O)OOC(=O)CC(C)CC(C)(C)C KFGFVPMRLOQXNB-UHFFFAOYSA-N 0.000 claims description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 2
- CARSMBZECAABMO-UHFFFAOYSA-N 3-chloro-2,6-dimethylbenzoic acid Chemical compound CC1=CC=C(Cl)C(C)=C1C(O)=O CARSMBZECAABMO-UHFFFAOYSA-N 0.000 claims description 2
- IWLZOFJJPYLFSF-UHFFFAOYSA-N 4-azido-1-(4-azidophenyl)-7-oxabicyclo[4.1.0]hepta-2,4-diene Chemical compound N(=[N+]=[N-])C1=CC2C(C=C1)(C1=CC=C(C=C1)N=[N+]=[N-])O2 IWLZOFJJPYLFSF-UHFFFAOYSA-N 0.000 claims description 2
- PQXPAFTXDVNANI-UHFFFAOYSA-N 4-azidobenzoic acid Chemical compound OC(=O)C1=CC=C(N=[N+]=[N-])C=C1 PQXPAFTXDVNANI-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 2
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
- 244000028419 Styrax benzoin Species 0.000 claims description 2
- 235000000126 Styrax benzoin Nutrition 0.000 claims description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 claims description 2
- XUGUHTGSMPZQIW-UHFFFAOYSA-N [[4-(4-diazonioiminocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-ylidene]hydrazinylidene]azanide Chemical group C1=CC(N=[N+]=[N-])=CC=C1C1=CC=C(N=[N+]=[N-])C=C1 XUGUHTGSMPZQIW-UHFFFAOYSA-N 0.000 claims description 2
- HWEONUWVYWIJPF-UHFFFAOYSA-N [[4-[2-(4-diazonioiminocyclohexa-2,5-dien-1-ylidene)ethylidene]cyclohexa-2,5-dien-1-ylidene]hydrazinylidene]azanide Chemical group C1=CC(N=[N+]=[N-])=CC=C1C=CC1=CC=C(N=[N+]=[N-])C=C1 HWEONUWVYWIJPF-UHFFFAOYSA-N 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 2
- CHFBCXOSLARLKB-UHFFFAOYSA-N bis(4-azidophenyl)methanone Chemical compound C1=CC(N=[N+]=[N-])=CC=C1C(=O)C1=CC=C(N=[N+]=[N-])C=C1 CHFBCXOSLARLKB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 2
- SPTHWAJJMLCAQF-UHFFFAOYSA-M ctk4f8481 Chemical compound [O-]O.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-M 0.000 claims description 2
- XJOBOFWTZOKMOH-UHFFFAOYSA-N decanoyl decaneperoxoate Chemical class CCCCCCCCCC(=O)OOC(=O)CCCCCCCCC XJOBOFWTZOKMOH-UHFFFAOYSA-N 0.000 claims description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 2
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims description 2
- HYYYTIDWAIQGHI-UHFFFAOYSA-L disodium;5-azido-2-[2-(4-azido-2-sulfonatophenyl)ethenyl]benzenesulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC(N=[N+]=[N-])=CC=C1C=CC1=CC=C(N=[N+]=[N-])C=C1S([O-])(=O)=O HYYYTIDWAIQGHI-UHFFFAOYSA-L 0.000 claims description 2
- 235000019382 gum benzoic Nutrition 0.000 claims description 2
- LDHQCZJRKDOVOX-IHWYPQMZSA-N isocrotonic acid Chemical compound C\C=C/C(O)=O LDHQCZJRKDOVOX-IHWYPQMZSA-N 0.000 claims description 2
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 claims description 2
- DNYZBFWKVMKMRM-UHFFFAOYSA-N n-benzhydrylidenehydroxylamine Chemical compound C=1C=CC=CC=1C(=NO)C1=CC=CC=C1 DNYZBFWKVMKMRM-UHFFFAOYSA-N 0.000 claims description 2
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 claims description 2
- 125000005385 peroxodisulfate group Chemical group 0.000 claims description 2
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 claims description 2
- CTRLRINCMYICJO-UHFFFAOYSA-N phenyl azide Chemical compound [N-]=[N+]=NC1=CC=CC=C1 CTRLRINCMYICJO-UHFFFAOYSA-N 0.000 claims description 2
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 claims description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 2
- 229920001897 terpolymer Polymers 0.000 claims description 2
- YOEYNURYLFDCEV-UHFFFAOYSA-N tert-butyl hydroxy carbonate Chemical compound CC(C)(C)OC(=O)OO YOEYNURYLFDCEV-UHFFFAOYSA-N 0.000 claims description 2
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- 239000007858 starting material Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical group C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 150000003751 zinc Chemical class 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
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L13/00—Compositions of rubbers containing carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005047115A DE102005047115A1 (de) | 2005-09-30 | 2005-09-30 | Vernetzbare Zusammensetzungen, Verfahren zu deren Herstellung und deren Verwendung |
| EP06019724A EP1770119B1 (de) | 2005-09-30 | 2006-09-21 | Vernetzbare Exlastomerzusammensetzungen, Verfahren zu deren Herstellung und deren Verwendung |
| DE502006005446T DE502006005446D1 (de) | 2005-09-30 | 2006-09-21 | Vernetzbare Exlastomerzusammensetzungen, Verfahren zu deren Herstellung und deren Verwendung |
| AT06019724T ATE449814T1 (de) | 2005-09-30 | 2006-09-21 | Vernetzbare exlastomerzusammensetzungen, verfahren zu deren herstellung und deren verwendung |
| US11/526,544 US7645833B2 (en) | 2005-09-30 | 2006-09-25 | Crosslinkable compositions, processes for the preparation thereof and the use thereof |
| TW095136122A TWI415888B (zh) | 2005-09-30 | 2006-09-29 | 可交聯組成物，其製法及用途 |
| JP2006268571A JP5179036B2 (ja) | 2005-09-30 | 2006-09-29 | 架橋性組成物、その調製方法およびその使用 |
| KR1020060095356A KR101361943B1 (ko) | 2005-09-30 | 2006-09-29 | 가교성 조성물, 이의 제조 방법 및 이의 용도 |
| CN2006101447446A CN1990541B (zh) | 2005-09-30 | 2006-09-29 | 可交联组合物,其制备方法及其应用 |
| BRPI0604006-3A BRPI0604006A (pt) | 2005-09-30 | 2006-10-02 | composições reticuláveis, processos para o preparo das mesmas e uso das mesmas |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005047115A DE102005047115A1 (de) | 2005-09-30 | 2005-09-30 | Vernetzbare Zusammensetzungen, Verfahren zu deren Herstellung und deren Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102005047115A1 true DE102005047115A1 (de) | 2007-04-05 |
Family
ID=37440978
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102005047115A Withdrawn DE102005047115A1 (de) | 2005-09-30 | 2005-09-30 | Vernetzbare Zusammensetzungen, Verfahren zu deren Herstellung und deren Verwendung |
| DE502006005446T Active DE502006005446D1 (de) | 2005-09-30 | 2006-09-21 | Vernetzbare Exlastomerzusammensetzungen, Verfahren zu deren Herstellung und deren Verwendung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE502006005446T Active DE502006005446D1 (de) | 2005-09-30 | 2006-09-21 | Vernetzbare Exlastomerzusammensetzungen, Verfahren zu deren Herstellung und deren Verwendung |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7645833B2 (https=) |
| EP (1) | EP1770119B1 (https=) |
| JP (1) | JP5179036B2 (https=) |
| KR (1) | KR101361943B1 (https=) |
| CN (1) | CN1990541B (https=) |
| AT (1) | ATE449814T1 (https=) |
| BR (1) | BRPI0604006A (https=) |
| DE (2) | DE102005047115A1 (https=) |
| TW (1) | TWI415888B (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE602007014124D1 (de) * | 2007-12-05 | 2011-06-01 | Pirelli | Reifen und vernetzbare elastomerzusammensetzungen mit diazidvernetzungsmitteln |
| WO2009155728A1 (en) * | 2008-06-23 | 2009-12-30 | Lanxess Deutschland Gmbh | Carbon nanotube containing rubber compositions |
| CN101613495B (zh) * | 2008-06-23 | 2013-03-27 | 朗盛德国有限责任公司 | 含纳米碳管的橡胶组合物 |
| EP2473279B1 (en) * | 2009-08-31 | 2014-04-02 | LANXESS Deutschland GmbH | Metathesis of a nitrile rubber in the presence of a transition metal catalyst |
| US8691884B2 (en) | 2010-11-24 | 2014-04-08 | Tyco Electronics Corporation | Crosslinked flame retardant thermoplastic elastomer gels |
| US8404172B2 (en) | 2010-11-24 | 2013-03-26 | Tyco Electronics Corporation | Methods of processing high service temperature hydrocarbon gels |
| CN102477179B (zh) * | 2010-11-25 | 2015-05-13 | 比亚迪股份有限公司 | 一种耐油橡胶组合物和耐油橡胶及其制备方法 |
| TWI638871B (zh) * | 2012-11-30 | 2018-10-21 | 日商琳得科股份有限公司 | Substance composition, subsequent sheet and electronic device |
| WO2014148612A1 (ja) * | 2013-03-22 | 2014-09-25 | 日本ゼオン株式会社 | ニトリル基含有共重合体ゴム、架橋性ゴム組成物、およびゴム架橋物 |
| JP6137899B2 (ja) * | 2013-03-26 | 2017-05-31 | 日信工業株式会社 | 炭素繊維複合材料及びその製造方法 |
| WO2018007579A1 (en) * | 2016-07-08 | 2018-01-11 | Covestro Deutschland Ag | Process for producing 3d structures from rubber material and its products |
| WO2020004243A1 (ja) * | 2018-06-29 | 2020-01-02 | 株式会社クラレ | ゴム組成物 |
| CN109206686A (zh) * | 2018-07-14 | 2019-01-15 | 桂林理工大学 | 一种丁腈橡胶-金属复合密封材料及其制备方法 |
| RU2755481C1 (ru) * | 2020-07-07 | 2021-09-16 | Общество с ограниченной ответственностью "Газпром 335" | Эластомерная композиция и способ ее получения |
| EP4392267A1 (en) * | 2021-08-27 | 2024-07-03 | ARLANXEO Deutschland GmbH | Stabilized polymer compositions comprising organic acids and diene rubbers functionalized with units comprising carboxylic acid groups |
| CN116320958A (zh) * | 2023-03-07 | 2023-06-23 | 歌尔股份有限公司 | 振膜和发声装置 |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3700637A (en) * | 1970-05-08 | 1972-10-24 | Shell Oil Co | Diene-nitrile rubbers |
| DE2539132C2 (de) | 1975-09-03 | 1987-04-09 | Bayer Ag, 5090 Leverkusen | Verwendung hydrierter Dien-Copolymere als temperaturbeständige Materialien auf dem Dichtungssektor |
| CA1203047A (en) * | 1982-12-08 | 1986-04-08 | Hormoz Azizian | Polymer hydrogenation process |
| CA1220300A (en) * | 1982-12-08 | 1987-04-07 | Polysar Limited | Polymer hydrogenation process |
| DE3329974A1 (de) * | 1983-08-19 | 1985-02-28 | Bayer Ag, 5090 Leverkusen | Herstellung von hydrierten nitrilkautschuken |
| US4525517A (en) * | 1984-02-13 | 1985-06-25 | Polysar Limited | Vulcanizable polymer compositions with improved scorch |
| DE3433392A1 (de) * | 1984-09-12 | 1986-03-20 | Bayer Ag, 5090 Leverkusen | Hydrierung nitrilgruppenhaltiger ungesaettigter polymerer |
| DE3529252A1 (de) * | 1985-08-16 | 1987-02-19 | Bayer Ag | Verfahren zur selektiven hydrierung ungesaettigter verbindungen |
| DE3540918A1 (de) * | 1985-11-19 | 1987-05-21 | Bayer Ag | Verfahren zur selektiven hydrierung ungesaettigter verbindungen |
| DE3541689A1 (de) * | 1985-11-26 | 1987-05-27 | Bayer Ag | Verfahren zur selektiven hydrierung nitrilgruppenhaltiger ungesaettigter polymerer |
| US4952634A (en) * | 1987-01-21 | 1990-08-28 | Synthetic Products Company | Curable carboxylated polymers containing polymeric polyvalent metal salt crosslinking agents |
| JPH0796629B2 (ja) * | 1987-06-29 | 1995-10-18 | 日本ゼオン株式会社 | ゴム組成物 |
| US4816525A (en) | 1987-07-06 | 1989-03-28 | University Of Waterloo | Polymer hydrogenation process |
| DE4025781A1 (de) | 1990-08-15 | 1992-02-20 | Bayer Ag | Hydrierte butadien/isopren/(meth-)acrylnitril- copolymerisate |
| JP3622809B2 (ja) * | 1995-09-14 | 2005-02-23 | 日本ゼオン株式会社 | エチレン性不飽和カルボン酸金属塩含有エラストマー組成物および加硫エラストマーの成形方法 |
| JP3770285B2 (ja) | 1996-09-27 | 2006-04-26 | 日本ゼオン株式会社 | カルボキシル化ニトリル基含有高飽和共重合体ゴム |
| JPH10279734A (ja) * | 1997-03-31 | 1998-10-20 | Nippon Zeon Co Ltd | エチレン性不飽和カルボン酸金属塩含有加硫性ゴム組成物 |
| US6207752B1 (en) * | 1997-12-10 | 2001-03-27 | Advanced Elastomer Systems Lp | Thermoplastic vulcanizates of carboxylated nitrile rubber and thermoplastic polyurethanes |
| ES2280244T3 (es) * | 1999-12-03 | 2007-09-16 | China Petro-Chemical Corporation | Caucho en polvo totalmente vulcanizado con diametro de particula controlable, procedimiento de preparacion y uso del mismo. |
| CA2304501A1 (en) | 2000-04-10 | 2001-10-10 | Bayer Inc. | Process for hydrogenating carboxylated nitrile rubber, the hydrogenated rubber and its uses |
| CA2308876A1 (en) * | 2000-05-12 | 2001-11-12 | Bayer Inc. | Improved rubber composition |
| CA2329844A1 (en) * | 2000-12-28 | 2002-06-28 | Bayer Inc. | Esbo enhanced hydrogenation |
| DE10102047A1 (de) * | 2001-01-17 | 2002-07-18 | Bayer Ag | Kautschukmischungen für Walzenbeläge |
| CA2357089A1 (en) * | 2001-09-07 | 2003-03-07 | Bayer Inc. | Elastomeric compositions |
| CA2409429A1 (en) * | 2002-10-17 | 2004-04-17 | Bayer Inc. | Hydrogenated nitrile rubber composites with improved proccesability |
| CA2409436A1 (en) * | 2002-10-17 | 2004-04-17 | Bayer Inc. | Polymer composites comprising low molecular weight nitrile rubber |
| CA2413636A1 (en) * | 2002-12-05 | 2004-06-05 | Bayer Inc. | Adhesive compositions |
| DE10307137A1 (de) * | 2003-02-20 | 2004-09-02 | Bayer Ag | Zusammensetzung |
| DE10327452A1 (de) * | 2003-06-18 | 2005-01-05 | Bayer Materialscience Ag | Klebstoffe |
| US7351769B2 (en) * | 2004-01-26 | 2008-04-01 | Freudenberg-Nok General Partnership | Dynamic vulcanization of elastomers with in-situ polymerization |
-
2005
- 2005-09-30 DE DE102005047115A patent/DE102005047115A1/de not_active Withdrawn
-
2006
- 2006-09-21 DE DE502006005446T patent/DE502006005446D1/de active Active
- 2006-09-21 AT AT06019724T patent/ATE449814T1/de active
- 2006-09-21 EP EP06019724A patent/EP1770119B1/de active Active
- 2006-09-25 US US11/526,544 patent/US7645833B2/en active Active
- 2006-09-29 JP JP2006268571A patent/JP5179036B2/ja active Active
- 2006-09-29 CN CN2006101447446A patent/CN1990541B/zh active Active
- 2006-09-29 TW TW095136122A patent/TWI415888B/zh active
- 2006-09-29 KR KR1020060095356A patent/KR101361943B1/ko active Active
- 2006-10-02 BR BRPI0604006-3A patent/BRPI0604006A/pt active Search and Examination
Also Published As
| Publication number | Publication date |
|---|---|
| EP1770119A1 (de) | 2007-04-04 |
| US20090292064A1 (en) | 2009-11-26 |
| BRPI0604006A (pt) | 2007-08-21 |
| CN1990541A (zh) | 2007-07-04 |
| TW200726806A (en) | 2007-07-16 |
| JP2007100089A (ja) | 2007-04-19 |
| DE502006005446D1 (de) | 2010-01-07 |
| JP5179036B2 (ja) | 2013-04-10 |
| US7645833B2 (en) | 2010-01-12 |
| ATE449814T1 (de) | 2009-12-15 |
| CN1990541B (zh) | 2012-06-20 |
| TWI415888B (zh) | 2013-11-21 |
| KR101361943B1 (ko) | 2014-02-12 |
| EP1770119B1 (de) | 2009-11-25 |
| KR20070037372A (ko) | 2007-04-04 |
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