CA2359148A1 - Tack free surface cures of polymers by organic peroxides in the presence of air - Google Patents
Tack free surface cures of polymers by organic peroxides in the presence of air Download PDFInfo
- Publication number
- CA2359148A1 CA2359148A1 CA002359148A CA2359148A CA2359148A1 CA 2359148 A1 CA2359148 A1 CA 2359148A1 CA 002359148 A CA002359148 A CA 002359148A CA 2359148 A CA2359148 A CA 2359148A CA 2359148 A1 CA2359148 A1 CA 2359148A1
- Authority
- CA
- Canada
- Prior art keywords
- composition
- peroxide
- compound
- sulfur
- free radical
- 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.)
- Abandoned
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- 229920000642 polymer Polymers 0.000 title claims abstract description 65
- 150000001451 organic peroxides Chemical class 0.000 title claims description 27
- 239000000203 mixture Substances 0.000 claims abstract description 220
- 150000001875 compounds Chemical class 0.000 claims abstract description 100
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 93
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 89
- 239000011593 sulfur Substances 0.000 claims abstract description 86
- 150000003254 radicals Chemical class 0.000 claims abstract description 61
- 239000003999 initiator Substances 0.000 claims abstract description 59
- 229920001021 polysulfide Polymers 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 25
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229910001882 dioxygen Inorganic materials 0.000 claims abstract description 22
- 238000010059 sulfur vulcanization Methods 0.000 claims abstract description 20
- 230000008569 process Effects 0.000 claims abstract description 16
- 229920002379 silicone rubber Polymers 0.000 claims abstract description 16
- 238000000354 decomposition reaction Methods 0.000 claims abstract description 7
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000002978 peroxides Chemical class 0.000 claims description 136
- 229920001971 elastomer Polymers 0.000 claims description 64
- 229920003192 poly(bis maleimide) Polymers 0.000 claims description 53
- 239000000806 elastomer Substances 0.000 claims description 40
- 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 30
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- CPGFMWPQXUXQRX-UHFFFAOYSA-N 3-amino-3-(4-fluorophenyl)propanoic acid Chemical compound OC(=O)CC(N)C1=CC=C(F)C=C1 CPGFMWPQXUXQRX-UHFFFAOYSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 229920002681 hypalon Polymers 0.000 claims description 15
- 238000013329 compounding Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 8
- 150000002894 organic compounds Chemical class 0.000 claims description 8
- 239000004709 Chlorinated polyethylene Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229920002943 EPDM rubber Polymers 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000004594 Masterbatch (MB) Substances 0.000 claims description 4
- 239000005038 ethylene vinyl acetate Substances 0.000 claims description 4
- BUZICZZQJDLXJN-UHFFFAOYSA-N 3-azaniumyl-4-hydroxybutanoate Chemical compound OCC(N)CC(O)=O BUZICZZQJDLXJN-UHFFFAOYSA-N 0.000 claims description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 3
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- 125000003118 aryl group Chemical group 0.000 claims description 3
- 150000002019 disulfides Chemical class 0.000 claims description 3
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- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 claims description 3
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- 125000002015 acyclic group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229920000181 Ethylene propylene rubber Polymers 0.000 claims 2
- 239000004615 ingredient Substances 0.000 abstract description 15
- 150000003464 sulfur compounds Chemical class 0.000 abstract description 7
- 238000004132 cross linking Methods 0.000 description 79
- 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 69
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- 239000000654 additive Substances 0.000 description 41
- -1 triazole compounds Chemical class 0.000 description 38
- 239000003921 oil Substances 0.000 description 37
- VNDRMZTXEFFQDR-UHFFFAOYSA-N (piperidine-1-carbothioyltrisulfanyl) piperidine-1-carbodithioate Chemical compound C1CCCCN1C(=S)SSSSC(=S)N1CCCCC1 VNDRMZTXEFFQDR-UHFFFAOYSA-N 0.000 description 31
- 230000000704 physical effect Effects 0.000 description 26
- 239000005060 rubber Substances 0.000 description 24
- 239000006229 carbon black Substances 0.000 description 23
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 22
- 239000005077 polysulfide Substances 0.000 description 18
- 150000008117 polysulfides Polymers 0.000 description 18
- 235000021355 Stearic acid Nutrition 0.000 description 16
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 16
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 16
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- HLBZWYXLQJQBKU-UHFFFAOYSA-N 4-(morpholin-4-yldisulfanyl)morpholine Chemical compound C1COCCN1SSN1CCOCC1 HLBZWYXLQJQBKU-UHFFFAOYSA-N 0.000 description 15
- 239000003963 antioxidant agent Substances 0.000 description 15
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- XOZUGNYVDXMRKW-AATRIKPKSA-N azodicarbonamide Chemical compound NC(=O)\N=N\C(N)=O XOZUGNYVDXMRKW-AATRIKPKSA-N 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 11
- 230000001976 improved effect Effects 0.000 description 11
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 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 10
- 238000006243 chemical reaction Methods 0.000 description 10
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- 229910052725 zinc Inorganic materials 0.000 description 10
- 239000011701 zinc Substances 0.000 description 10
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- BLCKKNLGFULNRC-UHFFFAOYSA-L n,n-dimethylcarbamodithioate;nickel(2+) Chemical compound [Ni+2].CN(C)C([S-])=S.CN(C)C([S-])=S BLCKKNLGFULNRC-UHFFFAOYSA-L 0.000 description 8
- 239000004945 silicone rubber Substances 0.000 description 8
- 230000000996 additive effect Effects 0.000 description 7
- 230000003078 antioxidant effect Effects 0.000 description 7
- REQPQFUJGGOFQL-UHFFFAOYSA-N dimethylcarbamothioyl n,n-dimethylcarbamodithioate Chemical compound CN(C)C(=S)SC(=S)N(C)C REQPQFUJGGOFQL-UHFFFAOYSA-N 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 239000007789 gas Substances 0.000 description 6
- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 description 5
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 230000032683 aging Effects 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 229920006037 cross link polymer Polymers 0.000 description 5
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- 150000003839 salts Chemical class 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical class CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- PUKLCKVOVCZYKF-UHFFFAOYSA-N 1-[2-(2,5-dioxopyrrol-1-yl)ethyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCN1C(=O)C=CC1=O PUKLCKVOVCZYKF-UHFFFAOYSA-N 0.000 description 4
- UFFVWIGGYXLXPC-UHFFFAOYSA-N 1-[2-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1N1C(=O)C=CC1=O UFFVWIGGYXLXPC-UHFFFAOYSA-N 0.000 description 4
- PYVHLZLQVWXBDZ-UHFFFAOYSA-N 1-[6-(2,5-dioxopyrrol-1-yl)hexyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CCCCCCN1C(=O)C=CC1=O PYVHLZLQVWXBDZ-UHFFFAOYSA-N 0.000 description 4
- QGQBREBGIBKDOS-UHFFFAOYSA-N 2-cyclopenta-2,4-dien-1-ylidene-1,3-dithiolane Chemical compound S1CCSC1=C1C=CC=C1 QGQBREBGIBKDOS-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000005062 Polybutadiene Substances 0.000 description 4
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 4
- 150000004659 dithiocarbamates Chemical class 0.000 description 4
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- 239000007788 liquid Substances 0.000 description 4
- VILGDADBAQFRJE-UHFFFAOYSA-N n,n-bis(1,3-benzothiazol-2-ylsulfanyl)-2-methylpropan-2-amine Chemical compound C1=CC=C2SC(SN(SC=3SC4=CC=CC=C4N=3)C(C)(C)C)=NC2=C1 VILGDADBAQFRJE-UHFFFAOYSA-N 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- 230000000153 supplemental effect Effects 0.000 description 4
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- FPAZNLSVMWRGQB-UHFFFAOYSA-N 1,2-bis(tert-butylperoxy)-3,4-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=C(OOC(C)(C)C)C(OOC(C)(C)C)=C1C(C)C FPAZNLSVMWRGQB-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- QRYFCNPYGUORTK-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-yldisulfanyl)morpholine Chemical compound C1COCCN1SSC1=NC2=CC=CC=C2S1 QRYFCNPYGUORTK-UHFFFAOYSA-N 0.000 description 3
- UDQCDDZBBZNIFA-UHFFFAOYSA-N 4-methyl-1,3-dihydrobenzimidazole-2-thione Chemical compound CC1=CC=CC2=C1NC(=S)N2 UDQCDDZBBZNIFA-UHFFFAOYSA-N 0.000 description 3
- ODEURDFKGFSFKX-UHFFFAOYSA-N 4-tert-butylperoxy-4-methylpentan-2-one Chemical compound CC(=O)CC(C)(C)OOC(C)(C)C ODEURDFKGFSFKX-UHFFFAOYSA-N 0.000 description 3
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- 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 3
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- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 3
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- 125000004429 atom Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
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- 229920001194 natural rubber Polymers 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- QCAZHHXMIVSLMW-UHFFFAOYSA-N o-butyl (butoxycarbothioyldisulfanyl)methanethioate Chemical compound CCCCOC(=S)SSC(=S)OCCCC QCAZHHXMIVSLMW-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- PVFZKRMYBKEXBN-UHFFFAOYSA-N piperidine;piperidine-1-carbodithioic acid Chemical compound C1CCNCC1.SC(=S)N1CCCCC1 PVFZKRMYBKEXBN-UHFFFAOYSA-N 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- VLDHWMAJBNWALQ-UHFFFAOYSA-N sodium;3h-1,3-benzothiazole-2-thione Chemical compound [Na+].C1=CC=C2SC(S)=NC2=C1 VLDHWMAJBNWALQ-UHFFFAOYSA-N 0.000 description 1
- HUMLQUKVJARKRN-UHFFFAOYSA-M sodium;n,n-dibutylcarbamodithioate Chemical compound [Na+].CCCCN(C([S-])=S)CCCC HUMLQUKVJARKRN-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- SUEGWIXYCHISPX-UHFFFAOYSA-N sulfane trihydroxy(sulfanylidene)-lambda5-phosphane Chemical compound OP(O)(O)=S.S SUEGWIXYCHISPX-UHFFFAOYSA-N 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- CSKKAINPUYTTRW-UHFFFAOYSA-N tetradecoxycarbonyloxy tetradecyl carbonate Chemical compound CCCCCCCCCCCCCCOC(=O)OOC(=O)OCCCCCCCCCCCCCC CSKKAINPUYTTRW-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
- AUMBZPPBWALQRO-UHFFFAOYSA-L zinc;n,n-dibenzylcarbamodithioate Chemical compound [Zn+2].C=1C=CC=CC=1CN(C(=S)[S-])CC1=CC=CC=C1.C=1C=CC=CC=1CN(C(=S)[S-])CC1=CC=CC=C1 AUMBZPPBWALQRO-UHFFFAOYSA-L 0.000 description 1
- JGSUMMPGKPITGK-UHFFFAOYSA-L zinc;n,n-dipentylcarbamodithioate Chemical compound [Zn+2].CCCCCN(C([S-])=S)CCCCC.CCCCCN(C([S-])=S)CCCCC JGSUMMPGKPITGK-UHFFFAOYSA-L 0.000 description 1
- SZNCKQHFYDCMLZ-UHFFFAOYSA-L zinc;propan-2-yloxymethanedithioate Chemical compound [Zn+2].CC(C)OC([S-])=S.CC(C)OC([S-])=S SZNCKQHFYDCMLZ-UHFFFAOYSA-L 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
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)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Polyethers (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16448899P | 1999-11-09 | 1999-11-09 | |
| US60/164,488 | 1999-11-09 | ||
| PCT/US2000/030953 WO2001034680A1 (en) | 1999-11-09 | 2000-11-09 | Tack free surface cures of polymers by organic peroxides in the presence of air |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2359148A1 true CA2359148A1 (en) | 2001-05-17 |
Family
ID=22594715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002359148A Abandoned CA2359148A1 (en) | 1999-11-09 | 2000-11-09 | Tack free surface cures of polymers by organic peroxides in the presence of air |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP1149122A4 (zh) |
| JP (1) | JP2003514088A (zh) |
| CN (1) | CN1336939A (zh) |
| AU (1) | AU1596301A (zh) |
| BR (1) | BR0007426A (zh) |
| CA (1) | CA2359148A1 (zh) |
| HK (1) | HK1041278A1 (zh) |
| HU (1) | HUP0104979A3 (zh) |
| PL (1) | PL348765A1 (zh) |
| RU (1) | RU2001122163A (zh) |
| WO (1) | WO2001034680A1 (zh) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060148942A1 (en) * | 2004-12-30 | 2006-07-06 | The Goodyear Tire & Rubber Company | Rubber cure system and rubber composition incorporating same |
| WO2009103923A2 (fr) * | 2008-02-20 | 2009-08-27 | Sediver, Societe Europeenne D'isolateurs En Verre Et Composite | Procédé de fabrication d'un isolateur électrique avec un revêtement polymère contenant des agents anti-ozonants |
| JP5533208B2 (ja) * | 2010-05-06 | 2014-06-25 | 横浜ゴム株式会社 | ゴム組成物およびホース |
| BR112015022755B8 (pt) * | 2013-03-14 | 2020-08-04 | Arkema Inc | processo para a cura de uma composição de elastômeros, composição de elastômero, método para a fabricação de um artigo e processo para reduzir as incrustações por moldagem na presença de oxigênio durante a fabricação de artigos elastoméricos |
| CN105143330A (zh) | 2013-03-26 | 2015-12-09 | 阿克佐诺贝尔化学国际公司 | 交联epm和epdm的方法 |
| JP6707541B2 (ja) * | 2014-12-09 | 2020-06-10 | アーケマ・インコーポレイテッド | 大気酸素の存在下においてポリマーを架橋させるための組成物および方法 |
| JP6830063B2 (ja) * | 2014-12-09 | 2021-02-17 | アーケマ・インコーポレイテッド | 大気酸素の存在下でポリマーを架橋させるための組成物および方法 |
| GB201506876D0 (en) * | 2015-04-22 | 2015-06-03 | Uponor Innovation Ab | Polyolefin pipe |
| JP6579704B2 (ja) * | 2015-09-18 | 2019-09-25 | 株式会社ブリヂストン | ゴム組成物及び防振ゴム |
| JP2017222811A (ja) * | 2016-06-17 | 2017-12-21 | 株式会社ブリヂストン | ゴム組成物及びその製造方法 |
| JP2017222810A (ja) * | 2016-06-17 | 2017-12-21 | 株式会社ブリヂストン | ゴム組成物及びその製造方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4575522A (en) * | 1985-03-07 | 1986-03-11 | Hydril Company | Rubber composition for geothermal application |
| US4929665A (en) * | 1987-01-20 | 1990-05-29 | Dainippon Ink And Chemicals, Inc. | Thermoplastic resin composition |
| FR2612196B1 (fr) * | 1987-03-10 | 1989-06-16 | Rhone Poulenc Chimie | Polymeres thermostables a base de maleimides dont un bismaleimide siloxane et de diamines aromatiques et leurs procedes de preparation |
| CA2063478A1 (en) * | 1991-03-22 | 1992-09-23 | Michael F. Novits | Scorch extending curing/crosslinking compositions |
-
2000
- 2000-11-09 EP EP00978506A patent/EP1149122A4/en not_active Withdrawn
- 2000-11-09 HU HU0104979A patent/HUP0104979A3/hu unknown
- 2000-11-09 PL PL00348765A patent/PL348765A1/xx not_active Application Discontinuation
- 2000-11-09 CA CA002359148A patent/CA2359148A1/en not_active Abandoned
- 2000-11-09 JP JP2001537389A patent/JP2003514088A/ja not_active Withdrawn
- 2000-11-09 CN CN00802607A patent/CN1336939A/zh active Pending
- 2000-11-09 RU RU2001122163/04A patent/RU2001122163A/ru not_active Application Discontinuation
- 2000-11-09 AU AU15963/01A patent/AU1596301A/en not_active Abandoned
- 2000-11-09 BR BR0007426-8A patent/BR0007426A/pt not_active IP Right Cessation
- 2000-11-09 WO PCT/US2000/030953 patent/WO2001034680A1/en not_active Application Discontinuation
-
2002
- 2002-04-25 HK HK02103112.5A patent/HK1041278A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0104979A3 (en) | 2004-04-28 |
| BR0007426A (pt) | 2001-11-20 |
| RU2001122163A (ru) | 2003-06-10 |
| EP1149122A1 (en) | 2001-10-31 |
| CN1336939A (zh) | 2002-02-20 |
| HK1041278A1 (zh) | 2002-07-05 |
| JP2003514088A (ja) | 2003-04-15 |
| AU1596301A (en) | 2001-06-06 |
| EP1149122A4 (en) | 2003-03-12 |
| HUP0104979A2 (hu) | 2002-04-29 |
| WO2001034680A1 (en) | 2001-05-17 |
| PL348765A1 (en) | 2002-06-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |