NO121118B - - Google Patents
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- Publication number
- NO121118B NO121118B NO16318266A NO16318266A NO121118B NO 121118 B NO121118 B NO 121118B NO 16318266 A NO16318266 A NO 16318266A NO 16318266 A NO16318266 A NO 16318266A NO 121118 B NO121118 B NO 121118B
- Authority
- NO
- Norway
- Prior art keywords
- inhibitor
- carbamoyl
- vulcanization
- imidazolinon
- diimid
- Prior art date
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- 238000004073 vulcanization Methods 0.000 claims description 81
- 239000003112 inhibitor Substances 0.000 claims description 54
- -1 5, 5- dimethyl-3-hydantoinyl Chemical group 0.000 claims description 39
- 230000002028 premature Effects 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 22
- SCAKFUJVCFIFOX-UHFFFAOYSA-N 1-phenylsulfanylpyrrolidine-2,5-dione Chemical compound O=C1CCC(=O)N1SC1=CC=CC=C1 SCAKFUJVCFIFOX-UHFFFAOYSA-N 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- IUJLOAKJZQBENM-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-2-methylpropan-2-amine Chemical compound C1=CC=C2SC(SNC(C)(C)C)=NC2=C1 IUJLOAKJZQBENM-UHFFFAOYSA-N 0.000 claims description 16
- MHKLKWCYGIBEQF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-ylsulfanyl)morpholine Chemical compound C1COCCN1SC1=NC2=CC=CC=C2S1 MHKLKWCYGIBEQF-UHFFFAOYSA-N 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000003106 haloaryl group Chemical group 0.000 claims description 6
- 125000004999 nitroaryl group Chemical group 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 238000006731 degradation reaction Methods 0.000 claims description 5
- GVURDWLNXBZCCM-UHFFFAOYSA-N 2-butylsulfanylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(SCCCC)C(=O)C2=C1 GVURDWLNXBZCCM-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- UEZWYKZHXASYJN-UHFFFAOYSA-N cyclohexylthiophthalimide Chemical compound O=C1C2=CC=CC=C2C(=O)N1SC1CCCCC1 UEZWYKZHXASYJN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003944 tolyl group Chemical group 0.000 claims description 4
- 229920003244 diene elastomer Polymers 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000005366 cycloalkylthio group Chemical group 0.000 claims 1
- 229920001971 elastomer Polymers 0.000 description 38
- 239000005060 rubber Substances 0.000 description 38
- 239000000463 material Substances 0.000 description 30
- 239000000203 mixture Substances 0.000 description 15
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 12
- ZJNLYGOUHDJHMG-UHFFFAOYSA-N 1-n,4-n-bis(5-methylhexan-2-yl)benzene-1,4-diamine Chemical compound CC(C)CCC(C)NC1=CC=C(NC(C)CCC(C)C)C=C1 ZJNLYGOUHDJHMG-UHFFFAOYSA-N 0.000 description 11
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 10
- 229920003048 styrene butadiene rubber Polymers 0.000 description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
- 229920003052 natural elastomer Polymers 0.000 description 9
- 229920001194 natural rubber Polymers 0.000 description 9
- 244000043261 Hevea brasiliensis Species 0.000 description 8
- 241001441571 Hiodontidae Species 0.000 description 8
- 239000008380 degradant Substances 0.000 description 8
- UBUCNCOMADRQHX-UHFFFAOYSA-N N-Nitrosodiphenylamine Chemical compound C=1C=CC=CC=1N(N=O)C1=CC=CC=C1 UBUCNCOMADRQHX-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 239000011593 sulfur Substances 0.000 description 7
- 229920001897 terpolymer Polymers 0.000 description 6
- COXGJUYRQHEOGK-UHFFFAOYSA-N 1,3-bis(phenylsulfanyl)benzimidazol-2-one Chemical compound C1(=CC=CC=C1)SN1C(N(C2=C1C=CC=C2)SC2=CC=CC=C2)=O COXGJUYRQHEOGK-UHFFFAOYSA-N 0.000 description 5
- 239000005062 Polybutadiene Substances 0.000 description 5
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 5
- 229920002857 polybutadiene Polymers 0.000 description 5
- ZZMVLMVFYMGSMY-UHFFFAOYSA-N 4-n-(4-methylpentan-2-yl)-1-n-phenylbenzene-1,4-diamine Chemical compound C1=CC(NC(C)CC(C)C)=CC=C1NC1=CC=CC=C1 ZZMVLMVFYMGSMY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical class C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 4
- 239000013068 control sample Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- KGYMFMTXNIIZSP-UHFFFAOYSA-N 1-benzylsulfanylpyrrolidine-2,5-dione Chemical compound O=C1CCC(=O)N1SCC1=CC=CC=C1 KGYMFMTXNIIZSP-UHFFFAOYSA-N 0.000 description 3
- SNQDZVHQDVXJHD-UHFFFAOYSA-N 1-phenylsulfanylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1SC1=CC=CC=C1 SNQDZVHQDVXJHD-UHFFFAOYSA-N 0.000 description 3
- NMHKBABHRKQHOL-UHFFFAOYSA-N 2-phenylsulfanylisoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1SC1=CC=CC=C1 NMHKBABHRKQHOL-UHFFFAOYSA-N 0.000 description 3
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Natural products CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- 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
- 150000001993 dienes Chemical class 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229960002317 succinimide Drugs 0.000 description 3
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- FKZVQAMASQJHQX-UHFFFAOYSA-N 1,3-bis[(2-methylphenyl)sulfanyl]benzimidazol-2-one Chemical compound CC1=CC=CC=C1SN1C(=O)N(SC=2C(=CC=CC=2)C)C2=CC=CC=C21 FKZVQAMASQJHQX-UHFFFAOYSA-N 0.000 description 2
- CRKPWIQYNIRGJO-UHFFFAOYSA-N 1-phenyl-3-phenylsulfanylurea Chemical compound C=1C=CC=CC=1NC(=O)NSC1=CC=CC=C1 CRKPWIQYNIRGJO-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 229920005549 butyl rubber Polymers 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 235000019241 carbon black Nutrition 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 239000005061 synthetic rubber Substances 0.000 description 2
- 239000004636 vulcanized rubber Substances 0.000 description 2
- LFMQNMXVVXHZCC-UHFFFAOYSA-N 1,3-benzothiazol-2-yl n,n-diethylcarbamodithioate Chemical compound C1=CC=C2SC(SC(=S)N(CC)CC)=NC2=C1 LFMQNMXVVXHZCC-UHFFFAOYSA-N 0.000 description 1
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- AYTCQZIJADFSHG-UHFFFAOYSA-N 1-(2-nitrophenyl)sulfanylpyrrolidine-2,5-dione Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)SN1C(CCC1=O)=O AYTCQZIJADFSHG-UHFFFAOYSA-N 0.000 description 1
- DBHBUHCKUXHSTR-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfanylpyrrolidine-2,5-dione Chemical compound C1=CC(Cl)=CC=C1SN1C(=O)CCC1=O DBHBUHCKUXHSTR-UHFFFAOYSA-N 0.000 description 1
- FFFDOQHCUKCSNE-UHFFFAOYSA-N 1-(4-methylphenyl)sulfanylpyrrolidine-2,5-dione Chemical compound C1=CC(C)=CC=C1SN1C(=O)CCC1=O FFFDOQHCUKCSNE-UHFFFAOYSA-N 0.000 description 1
- RPQWWHDMMAFHDO-UHFFFAOYSA-N 1-butylsulfanylpyrrolidine-2,5-dione Chemical compound C(CCC)SN1C(CCC1=O)=O RPQWWHDMMAFHDO-UHFFFAOYSA-N 0.000 description 1
- VTUZUBREJXDULA-UHFFFAOYSA-N 1-cyclohexylsulfanylpyrrolidine-2,5-dione Chemical compound O=C1CCC(=O)N1SC1CCCCC1 VTUZUBREJXDULA-UHFFFAOYSA-N 0.000 description 1
- KOAQFALLABCUGQ-UHFFFAOYSA-N 1-cyclooctylsulfanylpyrrolidine-2,5-dione Chemical compound C1(CCCCCCC1)SN1C(CCC1=O)=O KOAQFALLABCUGQ-UHFFFAOYSA-N 0.000 description 1
- FAEIVUSYNUYMET-UHFFFAOYSA-N 1-dodecylsulfanylpyrrolidine-2,5-dione Chemical compound CCCCCCCCCCCCSN1C(=O)CCC1=O FAEIVUSYNUYMET-UHFFFAOYSA-N 0.000 description 1
- ASMHRQPUVUEGBD-UHFFFAOYSA-N 1-methylsulfanylpyrrolidine-2,5-dione Chemical compound CSN1C(=O)CCC1=O ASMHRQPUVUEGBD-UHFFFAOYSA-N 0.000 description 1
- WABFDYYOOKYPRW-UHFFFAOYSA-N 1-propan-2-ylsulfanylpyrrolidine-2,5-dione Chemical compound CC(C)SN1C(=O)CCC1=O WABFDYYOOKYPRW-UHFFFAOYSA-N 0.000 description 1
- STDGTTXRFKALAY-UHFFFAOYSA-N 1-propylsulfanylpyrrolidine-2,5-dione Chemical compound CCCSN1C(=O)CCC1=O STDGTTXRFKALAY-UHFFFAOYSA-N 0.000 description 1
- UOXLOACJWIPTNF-UHFFFAOYSA-N 1-tert-butylsulfanylpyrrolidine-2,5-dione Chemical compound CC(C)(C)SN1C(=O)CCC1=O UOXLOACJWIPTNF-UHFFFAOYSA-N 0.000 description 1
- HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical class CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 description 1
- BLZBPEKXXZSCRL-UHFFFAOYSA-N 2-(2-methylphenyl)sulfanylisoindole-1,3-dione Chemical compound CC1=CC=CC=C1SN1C(=O)C2=CC=CC=C2C1=O BLZBPEKXXZSCRL-UHFFFAOYSA-N 0.000 description 1
- MWRUNGXOGWGVSC-UHFFFAOYSA-N 2-(2-nitrophenyl)sulfanylisoindole-1,3-dione Chemical compound [O-][N+](=O)C1=CC=CC=C1SN1C(=O)C2=CC=CC=C2C1=O MWRUNGXOGWGVSC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MHNWGALOHVYLDZ-UHFFFAOYSA-N 2-(4-chlorophenyl)sulfanylisoindole-1,3-dione Chemical compound C1=CC(Cl)=CC=C1SN1C(=O)C2=CC=CC=C2C1=O MHNWGALOHVYLDZ-UHFFFAOYSA-N 0.000 description 1
- PMCSBSWCDNIWPQ-UHFFFAOYSA-N 2-dodecylsulfanylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(SCCCCCCCCCCCC)C(=O)C2=C1 PMCSBSWCDNIWPQ-UHFFFAOYSA-N 0.000 description 1
- FUEOUCBQKTVVHS-UHFFFAOYSA-N 2-naphthalen-1-ylsulfanylisoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1SC1=CC=CC2=CC=CC=C12 FUEOUCBQKTVVHS-UHFFFAOYSA-N 0.000 description 1
- TVHMHADGGSKDRC-UHFFFAOYSA-N 2-propan-2-ylsulfanylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(SC(C)C)C(=O)C2=C1 TVHMHADGGSKDRC-UHFFFAOYSA-N 0.000 description 1
- GZTZFOMIGGCAOI-UHFFFAOYSA-N 2-tert-butylsulfanylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(SC(C)(C)C)C(=O)C2=C1 GZTZFOMIGGCAOI-UHFFFAOYSA-N 0.000 description 1
- BUZICZZQJDLXJN-UHFFFAOYSA-N 3-azaniumyl-4-hydroxybutanoate Chemical compound OCC(N)CC(O)=O BUZICZZQJDLXJN-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000006232 furnace black Substances 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- BRHMVXPORIZQNX-UHFFFAOYSA-N methylsulfanylurea Chemical compound CSNC(N)=O BRHMVXPORIZQNX-UHFFFAOYSA-N 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 150000004005 nitrosamines Chemical class 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- IGXIQOFPTUWHFL-UHFFFAOYSA-N phenylsulfanylurea Chemical compound NC(=O)NSC1=CC=CC=C1 IGXIQOFPTUWHFL-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000010092 rubber production Methods 0.000 description 1
- AQHBWWRHIPVRBT-UHFFFAOYSA-N s-(1,3-thiazol-2-yl)thiohydroxylamine Chemical class NSC1=NC=CS1 AQHBWWRHIPVRBT-UHFFFAOYSA-N 0.000 description 1
- DIFCZTZSUFXWEJ-UHFFFAOYSA-N s-(4-butyl-1,3-benzothiazol-2-yl)thiohydroxylamine Chemical compound CCCCC1=CC=CC2=C1N=C(SN)S2 DIFCZTZSUFXWEJ-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical class CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000012991 xanthate Substances 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/43—Compounds containing sulfur bound to nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/08—Sulfenic acids; Derivatives thereof
- C07C313/18—Sulfenamides
- C07C313/26—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C313/30—Y being a hetero atom
- C07C313/34—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfenylureas
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/48—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/72—4,7-Endo-alkylene-iso-indoles
- C07D209/76—4,7-Endo-alkylene-iso-indoles with oxygen atoms in positions 1 and 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/38—One oxygen atom with acyl radicals or hetero atoms directly attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/26—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/43—Compounds containing sulfur bound to nitrogen
- C08K5/44—Sulfenamides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45946665A | 1965-05-27 | 1965-05-27 | |
| US459448A US3410864A (en) | 1965-05-27 | 1965-05-27 | Benzimidazolinones |
| US54973066A | 1966-05-12 | 1966-05-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO121118B true NO121118B (ja) | 1971-01-18 |
Family
ID=27412774
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO16318266A NO121118B (ja) | 1965-05-27 | 1966-05-26 | |
| NO411669A NO126733B (ja) | 1965-05-27 | 1969-10-16 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO411669A NO126733B (ja) | 1965-05-27 | 1969-10-16 |
Country Status (14)
| Country | Link |
|---|---|
| JP (3) | JPS4922938B1 (ja) |
| AT (2) | AT313571B (ja) |
| BE (2) | BE691486A (ja) |
| CA (2) | CA926537A (ja) |
| CH (1) | CH477481A (ja) |
| DE (2) | DE1620822C3 (ja) |
| FR (1) | FR1500844A (ja) |
| GB (2) | GB1155212A (ja) |
| LU (1) | LU51210A1 (ja) |
| NL (1) | NL152283B (ja) |
| NO (2) | NO121118B (ja) |
| PH (1) | PH10758A (ja) |
| SE (2) | SE383755B (ja) |
| SU (1) | SU391779A3 (ja) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2502656C2 (de) * | 1975-01-23 | 1982-06-24 | Bayer Ag, 5090 Leverkusen | Sulfenamide, deren Herstellung und Verwendung als Vulkanisationsverzögerer |
| US4080342A (en) * | 1976-12-06 | 1978-03-21 | Monsanto Company | N-(α-alkylbenzylthio)succinimide |
-
1966
- 1966-05-26 SE SE1226471A patent/SE383755B/xx unknown
- 1966-05-26 SE SE723666A patent/SE362645B/xx unknown
- 1966-05-26 CA CA961411A patent/CA926537A/en not_active Expired
- 1966-05-26 NO NO16318266A patent/NO121118B/no unknown
- 1966-05-26 CA CA961412A patent/CA926538A/en not_active Expired
- 1966-05-27 FR FR63312A patent/FR1500844A/fr not_active Expired
- 1966-05-27 JP JP3359466A patent/JPS4922938B1/ja active Pending
- 1966-05-27 DE DE1966M0069664 patent/DE1620822C3/de not_active Expired
- 1966-05-27 GB GB2382266D patent/GB1155212A/en not_active Expired
- 1966-05-27 AT AT537170A patent/AT313571B/de not_active IP Right Cessation
- 1966-05-27 LU LU51210D patent/LU51210A1/xx unknown
- 1966-05-27 GB GB2382366A patent/GB1155213A/en not_active Expired
- 1966-05-27 AT AT504866A patent/AT291552B/de not_active IP Right Cessation
- 1966-05-27 DE DE1966M0069665 patent/DE1620823C3/de not_active Expired
- 1966-05-27 CH CH773866A patent/CH477481A/fr not_active IP Right Cessation
- 1966-05-27 JP JP3359566A patent/JPS4922939B1/ja active Pending
- 1966-08-08 NL NL6611150A patent/NL152283B/xx not_active IP Right Cessation
- 1966-10-13 PH PH7689A patent/PH10758A/en unknown
- 1966-12-20 BE BE691486D patent/BE691486A/xx not_active IP Right Cessation
-
1967
- 1967-02-24 BE BE694563D patent/BE694563A/xx unknown
- 1967-05-11 JP JP2952667A patent/JPS4922940B1/ja active Pending
- 1967-05-12 SU SU1157351A patent/SU391779A3/ru active
-
1969
- 1969-10-16 NO NO411669A patent/NO126733B/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT291552B (de) | 1971-07-26 |
| CA926537A (en) | 1973-05-15 |
| SE362645B (ja) | 1973-12-17 |
| DE1620822B2 (de) | 1978-09-14 |
| BE694563A (ja) | 1967-08-24 |
| SE383755B (sv) | 1976-03-29 |
| DE1620823C3 (de) | 1979-09-27 |
| DE1620822A1 (de) | 1970-06-04 |
| DE1620823B2 (de) | 1978-10-26 |
| AT313571B (de) | 1974-02-25 |
| NO126733B (ja) | 1973-03-19 |
| NL152283B (nl) | 1977-02-15 |
| DE1620823A1 (de) | 1970-06-18 |
| FR1500844A (fr) | 1967-11-10 |
| PH10758A (en) | 1977-09-02 |
| BE691486A (ja) | 1967-06-20 |
| GB1155212A (en) | 1969-06-18 |
| CA926538A (en) | 1973-05-15 |
| CH477481A (fr) | 1969-08-31 |
| GB1155213A (en) | 1969-06-18 |
| JPS4922940B1 (ja) | 1974-06-12 |
| NL6611150A (ja) | 1967-11-13 |
| LU51210A1 (ja) | 1968-02-21 |
| JPS4922939B1 (ja) | 1974-06-12 |
| SU391779A3 (ja) | 1973-07-25 |
| DE1620822C3 (de) | 1979-05-10 |
| JPS4922938B1 (ja) | 1974-06-12 |
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