NO126733B - - Google Patents
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- Publication number
- NO126733B NO126733B NO411669A NO411669A NO126733B NO 126733 B NO126733 B NO 126733B NO 411669 A NO411669 A NO 411669A NO 411669 A NO411669 A NO 411669A NO 126733 B NO126733 B NO 126733B
- Authority
- NO
- Norway
- Prior art keywords
- phenylthio
- bis
- benzimidazolinone
- vulcanization
- benzimidazolinon
- Prior art date
Links
- -1 2-benzimidazolinon-1- yl Chemical group 0.000 claims description 55
- 238000004073 vulcanization Methods 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 38
- 239000003112 inhibitor Substances 0.000 claims description 18
- COXGJUYRQHEOGK-UHFFFAOYSA-N 1,3-bis(phenylsulfanyl)benzimidazol-2-one Chemical group C1(=CC=CC=C1)SN1C(N(C2=C1C=CC=C2)SC2=CC=CC=C2)=O COXGJUYRQHEOGK-UHFFFAOYSA-N 0.000 claims description 11
- SNQDZVHQDVXJHD-UHFFFAOYSA-N 1-phenylsulfanylpyrrole-2,5-dione Chemical group O=C1C=CC(=O)N1SC1=CC=CC=C1 SNQDZVHQDVXJHD-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- UEZWYKZHXASYJN-UHFFFAOYSA-N cyclohexylthiophthalimide Chemical group O=C1C2=CC=CC=C2C(=O)N1SC1CCCCC1 UEZWYKZHXASYJN-UHFFFAOYSA-N 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- GVURDWLNXBZCCM-UHFFFAOYSA-N 2-butylsulfanylisoindole-1,3-dione Chemical group C1=CC=C2C(=O)N(SCCCC)C(=O)C2=C1 GVURDWLNXBZCCM-UHFFFAOYSA-N 0.000 claims description 4
- TVHMHADGGSKDRC-UHFFFAOYSA-N 2-propan-2-ylsulfanylisoindole-1,3-dione Chemical group C1=CC=C2C(=O)N(SC(C)C)C(=O)C2=C1 TVHMHADGGSKDRC-UHFFFAOYSA-N 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000003106 haloaryl group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004999 nitroaryl group Chemical group 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 229920001971 elastomer Polymers 0.000 description 24
- 239000005060 rubber Substances 0.000 description 24
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 23
- 239000000047 product Substances 0.000 description 23
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- 239000000463 material Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 230000002028 premature Effects 0.000 description 14
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 14
- 241001441571 Hiodontidae Species 0.000 description 13
- 229910052717 sulfur Inorganic materials 0.000 description 13
- 239000011593 sulfur Substances 0.000 description 13
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- 229940091173 hydantoin Drugs 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000005864 Sulphur Substances 0.000 description 9
- MHKLKWCYGIBEQF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-ylsulfanyl)morpholine Chemical compound C1COCCN1SC1=NC2=CC=CC=C2S1 MHKLKWCYGIBEQF-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 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 description 7
- JWUKZUIGOJBEPC-UHFFFAOYSA-N phenyl thiohypochlorite Chemical compound ClSC1=CC=CC=C1 JWUKZUIGOJBEPC-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 229920003048 styrene butadiene rubber Polymers 0.000 description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 229920003052 natural elastomer Polymers 0.000 description 6
- 229920001194 natural rubber Polymers 0.000 description 6
- 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 5
- 244000043261 Hevea brasiliensis Species 0.000 description 5
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical class C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 5
- 239000008380 degradant Substances 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 229920001897 terpolymer Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- UBUCNCOMADRQHX-UHFFFAOYSA-N N-Nitrosodiphenylamine Chemical compound C=1C=CC=CC=1N(N=O)C1=CC=CC=C1 UBUCNCOMADRQHX-UHFFFAOYSA-N 0.000 description 4
- 239000005062 Polybutadiene Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910000071 diazene Inorganic materials 0.000 description 4
- 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 4
- 230000000694 effects Effects 0.000 description 4
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 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 3
- 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 3
- ICGXXXOBBGVZHE-UHFFFAOYSA-N 4-phenylsulfanyl-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione Chemical compound C1(=CC=CC=C1)SN1C(=O)C2C3C=CC(C2C1=O)C3 ICGXXXOBBGVZHE-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- 239000013068 control sample Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- AQHBWWRHIPVRBT-UHFFFAOYSA-N s-(1,3-thiazol-2-yl)thiohydroxylamine Chemical compound NSC1=NC=CS1 AQHBWWRHIPVRBT-UHFFFAOYSA-N 0.000 description 3
- 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
- SILNNFMWIMZVEQ-UHFFFAOYSA-N 1,3-dihydrobenzimidazol-2-one Chemical compound C1=CC=C2NC(O)=NC2=C1 SILNNFMWIMZVEQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- MYZJVHWTYYGIGJ-UHFFFAOYSA-N 3-phenylsulfanyl-1H-benzimidazol-2-one Chemical compound C1(=CC=CC=C1)SN1C(NC2=C1C=CC=C2)=O MYZJVHWTYYGIGJ-UHFFFAOYSA-N 0.000 description 2
- CIFFBTOJCKSRJY-UHFFFAOYSA-N 3α,4,7,7α-tetrahydro-1h-isoindole-1,3(2h)-dione Chemical compound C1C=CCC2C(=O)NC(=O)C21 CIFFBTOJCKSRJY-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 239000005061 synthetic rubber Substances 0.000 description 2
- KNDQHSIWLOJIGP-RNGGSSJXSA-N (3ar,4r,7s,7as)-rel-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione Chemical compound C1[C@@H]2[C@@H]3C(=O)OC(=O)[C@@H]3[C@H]1C=C2 KNDQHSIWLOJIGP-RNGGSSJXSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- 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
- FEZZHMSLBRCBKQ-UHFFFAOYSA-N 1-(2-chlorophenyl)sulfanylpyrrole-2,5-dione Chemical compound ClC1=C(C=CC=C1)SN1C(C=CC1=O)=O FEZZHMSLBRCBKQ-UHFFFAOYSA-N 0.000 description 1
- GENWXIQCTIHXSJ-UHFFFAOYSA-N 1-benzylsulfanylpyrrole-2,5-dione Chemical compound C(C1=CC=CC=C1)SN1C(C=CC1=O)=O GENWXIQCTIHXSJ-UHFFFAOYSA-N 0.000 description 1
- TXASOSWGTXLJGN-UHFFFAOYSA-N 1-cyclohexylsulfanylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1SC1CCCCC1 TXASOSWGTXLJGN-UHFFFAOYSA-N 0.000 description 1
- TTYNDVJJABKTSX-UHFFFAOYSA-N 1-dodecylsulfanylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCSN1C(=O)C=CC1=O TTYNDVJJABKTSX-UHFFFAOYSA-N 0.000 description 1
- FNSSTBIJTNHDEU-UHFFFAOYSA-N 1-ethylsulfanylpyrrole-2,5-dione Chemical compound CCSN1C(=O)C=CC1=O FNSSTBIJTNHDEU-UHFFFAOYSA-N 0.000 description 1
- OEJRXBLIWXOPSM-UHFFFAOYSA-N 1-methylsulfanylpyrrole-2,5-dione Chemical compound CSN1C(=O)C=CC1=O OEJRXBLIWXOPSM-UHFFFAOYSA-N 0.000 description 1
- SCAKFUJVCFIFOX-UHFFFAOYSA-N 1-phenylsulfanylpyrrolidine-2,5-dione Chemical compound O=C1CCC(=O)N1SC1=CC=CC=C1 SCAKFUJVCFIFOX-UHFFFAOYSA-N 0.000 description 1
- UGYIJWINFKSVKG-UHFFFAOYSA-N 1-tert-butylsulfanylpyrrole-2,5-dione Chemical compound C(C)(C)(C)SN1C(C=CC1=O)=O UGYIJWINFKSVKG-UHFFFAOYSA-N 0.000 description 1
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 1
- HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical class CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 description 1
- LWJNWRITTQPNLQ-UHFFFAOYSA-N 2-(2-methylpropylsulfanyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(SCC(C)C)C(=O)C2=C1 LWJNWRITTQPNLQ-UHFFFAOYSA-N 0.000 description 1
- XOAUPDRAKPXFQO-UHFFFAOYSA-N 2-benzylsulfanylisoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1SCC1=CC=CC=C1 XOAUPDRAKPXFQO-UHFFFAOYSA-N 0.000 description 1
- DLNZFRJQMKFUFZ-UHFFFAOYSA-N 2-cyclooctylsulfanylisoindole-1,3-dione Chemical compound C1(CCCCCCC1)SN1C(C=2C(C1=O)=CC=CC2)=O DLNZFRJQMKFUFZ-UHFFFAOYSA-N 0.000 description 1
- WOTMEGYCCPNSSQ-UHFFFAOYSA-N 2-ethylsulfanylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(SCC)C(=O)C2=C1 WOTMEGYCCPNSSQ-UHFFFAOYSA-N 0.000 description 1
- FJUBYDNFUMXCFS-UHFFFAOYSA-N 2-hexylsulfanylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(SCCCCCC)C(=O)C2=C1 FJUBYDNFUMXCFS-UHFFFAOYSA-N 0.000 description 1
- WTLUQUPRKDCBHG-UHFFFAOYSA-N 2-methylsulfanylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(SC)C(=O)C2=C1 WTLUQUPRKDCBHG-UHFFFAOYSA-N 0.000 description 1
- RSIYOALCKHUVIG-UHFFFAOYSA-N 2-octylsulfanylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(SCCCCCCCC)C(=O)C2=C1 RSIYOALCKHUVIG-UHFFFAOYSA-N 0.000 description 1
- VHWBDUXHCUUUMH-UHFFFAOYSA-N 2-pentylsulfanylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(SCCCCC)C(=O)C2=C1 VHWBDUXHCUUUMH-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
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-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
- QRFTXHFUNIFHST-UHFFFAOYSA-N 4,5,6,7-tetrabromoisoindole-1,3-dione Chemical compound BrC1=C(Br)C(Br)=C2C(=O)NC(=O)C2=C1Br QRFTXHFUNIFHST-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- KBODJKKATMAHCT-UHFFFAOYSA-N C(C)(C)(C)SN1C(NC2=C1C=CC=C2)=O Chemical compound C(C)(C)(C)SN1C(NC2=C1C=CC=C2)=O KBODJKKATMAHCT-UHFFFAOYSA-N 0.000 description 1
- JXUNSYPYBMYQOZ-UHFFFAOYSA-N C(C)(C)SN1C(C=CC1=O)=O Chemical compound C(C)(C)SN1C(C=CC1=O)=O JXUNSYPYBMYQOZ-UHFFFAOYSA-N 0.000 description 1
- AUIDOZHPIWYJFA-UHFFFAOYSA-N C(CC)SN1C(C=CC1=O)=O Chemical compound C(CC)SN1C(C=CC1=O)=O AUIDOZHPIWYJFA-UHFFFAOYSA-N 0.000 description 1
- AQECWCBHRSTXDR-UHFFFAOYSA-N C1(=C(C=CC=C1)SN1C(C=CC1=O)=O)C Chemical compound C1(=C(C=CC=C1)SN1C(C=CC1=O)=O)C AQECWCBHRSTXDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Natural products CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- BRPCFMORAAPPRK-UHFFFAOYSA-N O=C(NC1=C2C=CC=C1)N2SC1(C=CC=CC1)Cl Chemical compound O=C(NC1=C2C=CC=C1)N2SC1(C=CC=CC1)Cl BRPCFMORAAPPRK-UHFFFAOYSA-N 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- LTTMELGPIWMUHC-UHFFFAOYSA-N [N+](=O)([O-])C1=C(C=CC=C1)SN1C(C=CC1=O)=O Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)SN1C(C=CC1=O)=O LTTMELGPIWMUHC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- WAKPYRHUVBUCKQ-UHFFFAOYSA-N benzene;chloro thiohypochlorite Chemical compound ClSCl.C1=CC=CC=C1 WAKPYRHUVBUCKQ-UHFFFAOYSA-N 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- CMKBCTPCXZNQKX-UHFFFAOYSA-N cyclohexanethiol Chemical compound SC1CCCCC1 CMKBCTPCXZNQKX-UHFFFAOYSA-N 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012467 final product 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
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000178 monomer 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 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 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical class CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 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
- 238000004448 titration Methods 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000004636 vulcanized rubber Substances 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)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (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 |
|---|---|
| NO126733B true NO126733B (US07582779-20090901-C00044.png) | 1973-03-19 |
Family
ID=27412774
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO16318266A NO121118B (US07582779-20090901-C00044.png) | 1965-05-27 | 1966-05-26 | |
| NO411669A NO126733B (US07582779-20090901-C00044.png) | 1965-05-27 | 1969-10-16 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO16318266A NO121118B (US07582779-20090901-C00044.png) | 1965-05-27 | 1966-05-26 |
Country Status (14)
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 SE723666A patent/SE362645B/xx unknown
- 1966-05-26 SE SE1226471A patent/SE383755B/xx unknown
- 1966-05-26 NO NO16318266A patent/NO121118B/no unknown
- 1966-05-26 CA CA961412A patent/CA926538A/en not_active Expired
- 1966-05-26 CA CA961411A patent/CA926537A/en not_active Expired
- 1966-05-27 DE DE1966M0069665 patent/DE1620823C3/de not_active Expired
- 1966-05-27 LU LU51210D patent/LU51210A1/xx unknown
- 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 JP JP3359566A patent/JPS4922939B1/ja active Pending
- 1966-05-27 CH CH773866A patent/CH477481A/fr not_active IP Right Cessation
- 1966-05-27 JP JP3359466A patent/JPS4922938B1/ja active Pending
- 1966-05-27 FR FR63312A patent/FR1500844A/fr not_active Expired
- 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 AT AT537170A patent/AT313571B/de not_active IP Right Cessation
- 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
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