DE1620822C3 - Phthalimide und deren Verwendung als Inhibitoren für die vorzeitige Vulkanisation von Kautschuk - Google Patents
Phthalimide und deren Verwendung als Inhibitoren für die vorzeitige Vulkanisation von KautschukInfo
- Publication number
- DE1620822C3 DE1620822C3 DE1966M0069664 DEM0069664A DE1620822C3 DE 1620822 C3 DE1620822 C3 DE 1620822C3 DE 1966M0069664 DE1966M0069664 DE 1966M0069664 DE M0069664 A DEM0069664 A DE M0069664A DE 1620822 C3 DE1620822 C3 DE 1620822C3
- Authority
- DE
- Germany
- Prior art keywords
- vulcanization
- rubber
- accelerators
- phthalimide
- premature
- 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.)
- Expired
Links
- 238000004073 vulcanization Methods 0.000 title claims description 45
- 229920001971 elastomer Polymers 0.000 title claims description 36
- 239000005060 rubber Substances 0.000 title claims description 36
- 125000005543 phthalimide group Chemical class 0.000 title claims description 21
- 230000002028 premature Effects 0.000 title claims description 21
- 239000003112 inhibitor Substances 0.000 title claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 claims description 10
- UEZWYKZHXASYJN-UHFFFAOYSA-N cyclohexylthiophthalimide Chemical compound O=C1C2=CC=CC=C2C(=O)N1SC1CCCCC1 UEZWYKZHXASYJN-UHFFFAOYSA-N 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 239000004071 soot Substances 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 6
- 239000003381 stabilizer Substances 0.000 claims description 6
- 238000012545 processing Methods 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- 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 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 230000003111 delayed effect Effects 0.000 claims description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims 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 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- AQHBWWRHIPVRBT-UHFFFAOYSA-N s-(1,3-thiazol-2-yl)thiohydroxylamine Chemical compound NSC1=NC=CS1 AQHBWWRHIPVRBT-UHFFFAOYSA-N 0.000 claims 4
- 239000004615 ingredient Substances 0.000 claims 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 2
- 238000003860 storage Methods 0.000 claims 2
- 239000004636 vulcanized rubber Substances 0.000 claims 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims 1
- JKGLRGGCGUQNEX-UHFFFAOYSA-N 2-(chloromethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCl)C(=O)C2=C1 JKGLRGGCGUQNEX-UHFFFAOYSA-N 0.000 claims 1
- WDRFYIPWHMGQPN-UHFFFAOYSA-N 2-chloroisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(Cl)C(=O)C2=C1 WDRFYIPWHMGQPN-UHFFFAOYSA-N 0.000 claims 1
- MNSGOOCAMMSKGI-UHFFFAOYSA-N N-(hydroxymethyl)phthalimide Chemical group C1=CC=C2C(=O)N(CO)C(=O)C2=C1 MNSGOOCAMMSKGI-UHFFFAOYSA-N 0.000 claims 1
- UBUCNCOMADRQHX-UHFFFAOYSA-N N-Nitrosodiphenylamine Chemical compound C=1C=CC=CC=1N(N=O)C1=CC=CC=C1 UBUCNCOMADRQHX-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 230000009471 action Effects 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 230000002411 adverse Effects 0.000 claims 1
- 238000003490 calendering Methods 0.000 claims 1
- 230000008859 change Effects 0.000 claims 1
- 238000013329 compounding Methods 0.000 claims 1
- 150000007973 cyanuric acids Chemical class 0.000 claims 1
- 239000002270 dispersing agent Substances 0.000 claims 1
- 150000007974 melamines Chemical class 0.000 claims 1
- 239000000025 natural resin Substances 0.000 claims 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical class ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 claims 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 1
- 150000003141 primary amines Chemical class 0.000 claims 1
- 229960004889 salicylic acid Drugs 0.000 claims 1
- 150000003672 ureas Chemical class 0.000 claims 1
- 241001441571 Hiodontidae Species 0.000 description 22
- 229910052717 sulfur Inorganic materials 0.000 description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 16
- 239000011593 sulfur Substances 0.000 description 15
- 229920003052 natural elastomer Polymers 0.000 description 12
- 229920001194 natural rubber Polymers 0.000 description 12
- 244000043261 Hevea brasiliensis Species 0.000 description 11
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 10
- MHKLKWCYGIBEQF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-ylsulfanyl)morpholine Chemical compound C1COCCN1SC1=NC2=CC=CC=C2S1 MHKLKWCYGIBEQF-UHFFFAOYSA-N 0.000 description 9
- 238000013459 approach Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 8
- 229920003048 styrene butadiene rubber Polymers 0.000 description 8
- -1 amine disulfide Chemical class 0.000 description 7
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000005062 Polybutadiene Substances 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000005299 abrasion Methods 0.000 description 6
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 6
- 229920002857 polybutadiene Polymers 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 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 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 5
- 235000021355 Stearic acid Nutrition 0.000 description 5
- OMOVVBIIQSXZSZ-UHFFFAOYSA-N [6-(4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3h-pyrano[3,4-b]oxepin-5-yl)-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-hydroxy-3-methylpentanoate Chemical compound CC12C(OC(=O)C(O)C(C)CC)C(OC=O)C(C3(C)C(CC(=O)OC4(C)COC(=O)CC43)OC(C)=O)C(=C)C32OC3CC1C=1C=COC=1 OMOVVBIIQSXZSZ-UHFFFAOYSA-N 0.000 description 5
- 239000010692 aromatic oil Substances 0.000 description 5
- 238000010073 coating (rubber) Methods 0.000 description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 5
- 239000008117 stearic acid Substances 0.000 description 5
- 239000011787 zinc oxide Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 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 4
- 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 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- 239000006232 furnace black Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- MPLXTVNFXWHSDS-UHFFFAOYSA-N 2-icosylsulfanylisoindole-1,3-dione Chemical compound C(CCCCCCCCCCCCCCCCCCC)SN1C(C=2C(C1=O)=CC=CC2)=O MPLXTVNFXWHSDS-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
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 229920003244 diene elastomer Polymers 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 239000005061 synthetic 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
- DIPUOCQXXYYIJO-UHFFFAOYSA-N 1-n,2-n-bis(5-methylhexan-2-yl)benzene-1,2-diamine Chemical compound CC(C)CCC(C)NC1=CC=CC=C1NC(C)CCC(C)C DIPUOCQXXYYIJO-UHFFFAOYSA-N 0.000 description 1
- HRURMTZJRSHLAV-UHFFFAOYSA-N 1-n,4-n-bis(1,4-dimethylcyclohexa-2,4-dien-1-yl)benzene-1,4-diamine Chemical compound C1=CC(C)=CCC1(C)NC(C=C1)=CC=C1NC1(C)C=CC(C)=CC1 HRURMTZJRSHLAV-UHFFFAOYSA-N 0.000 description 1
- HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical class CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 description 1
- AZLWWJDQARJADC-UHFFFAOYSA-N 2-(2-methylpentan-2-yl)-1-n-phenylbenzene-1,4-diamine Chemical compound CCCC(C)(C)C1=CC(N)=CC=C1NC1=CC=CC=C1 AZLWWJDQARJADC-UHFFFAOYSA-N 0.000 description 1
- UPTVJAJPBGIRLZ-UHFFFAOYSA-N 2-(trichloromethylsulfanyl)-3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical compound C1CC=CC2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C21 UPTVJAJPBGIRLZ-UHFFFAOYSA-N 0.000 description 1
- QCUMRMJNFQSKNO-UHFFFAOYSA-N 2-butan-2-ylsulfanylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(SC(C)CC)C(=O)C2=C1 QCUMRMJNFQSKNO-UHFFFAOYSA-N 0.000 description 1
- SKXMIPFTDZZRRQ-UHFFFAOYSA-N 2-cyclopentylsulfanylisoindole-1,3-dione Chemical compound C1(CCCC1)SN1C(C=2C(C1=O)=CC=CC2)=O SKXMIPFTDZZRRQ-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
- 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
- PFEFOHMLVFUELJ-UHFFFAOYSA-N 3-sulfanylideneisoindol-1-one Chemical compound C1=CC=C2C(=O)NC(=S)C2=C1 PFEFOHMLVFUELJ-UHFFFAOYSA-N 0.000 description 1
- ILFKHFQSRXTZMS-UHFFFAOYSA-N 7-methyl-3-sulfanylideneisoindol-1-one Chemical compound CC1=CC=CC2=C1C(=O)NC2=S ILFKHFQSRXTZMS-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-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
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000007859 condensation product Substances 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
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000009472 formulation Methods 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
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- YYHYWOPDNMFEAV-UHFFFAOYSA-N icosane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCCCS YYHYWOPDNMFEAV-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 230000000704 physical effect Effects 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
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920001897 terpolymer Polymers 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
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- ZUBNXRHITOZMOO-UHFFFAOYSA-N zinc;octadecanoic acid;oxygen(2-) Chemical compound [O-2].[Zn+2].CCCCCCCCCCCCCCCCCC(O)=O ZUBNXRHITOZMOO-UHFFFAOYSA-N 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
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- 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 (3)
| Publication Number | Publication Date |
|---|---|
| DE1620822A1 DE1620822A1 (de) | 1970-06-04 |
| DE1620822B2 DE1620822B2 (de) | 1978-09-14 |
| DE1620822C3 true DE1620822C3 (de) | 1979-05-10 |
Family
ID=27412774
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1966M0069665 Expired DE1620823C3 (de) | 1965-05-27 | 1966-05-27 | l-Trichlormethylmercapto-benztmidazolin-2-on-Derivate und ihre Verwendung |
| DE1966M0069664 Expired DE1620822C3 (de) | 1965-05-27 | 1966-05-27 | Phthalimide und deren Verwendung als Inhibitoren für die vorzeitige Vulkanisation von Kautschuk |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1966M0069665 Expired DE1620823C3 (de) | 1965-05-27 | 1966-05-27 | l-Trichlormethylmercapto-benztmidazolin-2-on-Derivate und ihre Verwendung |
Country Status (14)
| Country | Link |
|---|---|
| JP (3) | JPS4922938B1 (OSRAM) |
| AT (2) | AT291552B (OSRAM) |
| BE (2) | BE691486A (OSRAM) |
| CA (2) | CA926538A (OSRAM) |
| CH (1) | CH477481A (OSRAM) |
| DE (2) | DE1620823C3 (OSRAM) |
| FR (1) | FR1500844A (OSRAM) |
| GB (2) | GB1155213A (OSRAM) |
| LU (1) | LU51210A1 (OSRAM) |
| NL (1) | NL152283B (OSRAM) |
| NO (2) | NO121118B (OSRAM) |
| PH (1) | PH10758A (OSRAM) |
| SE (2) | SE383755B (OSRAM) |
| SU (1) | SU391779A3 (OSRAM) |
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 CA961412A patent/CA926538A/en not_active Expired
- 1966-05-26 CA CA961411A patent/CA926537A/en not_active Expired
- 1966-05-26 NO NO16318266A patent/NO121118B/no unknown
- 1966-05-27 AT AT504866A patent/AT291552B/de not_active IP Right Cessation
- 1966-05-27 LU LU51210D patent/LU51210A1/xx unknown
- 1966-05-27 JP JP3359466A patent/JPS4922938B1/ja active Pending
- 1966-05-27 DE DE1966M0069665 patent/DE1620823C3/de not_active Expired
- 1966-05-27 AT AT537170A patent/AT313571B/de not_active IP Right Cessation
- 1966-05-27 GB GB2382366A patent/GB1155213A/en not_active Expired
- 1966-05-27 GB GB2382266D patent/GB1155212A/en not_active Expired
- 1966-05-27 DE DE1966M0069664 patent/DE1620822C3/de not_active Expired
- 1966-05-27 CH CH773866A patent/CH477481A/fr not_active IP Right Cessation
- 1966-05-27 FR FR63312A patent/FR1500844A/fr not_active Expired
- 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 |
| SE383755B (sv) | 1976-03-29 |
| JPS4922939B1 (OSRAM) | 1974-06-12 |
| SU391779A3 (OSRAM) | 1973-07-25 |
| DE1620822A1 (de) | 1970-06-04 |
| GB1155213A (en) | 1969-06-18 |
| NL6611150A (OSRAM) | 1967-11-13 |
| DE1620822B2 (de) | 1978-09-14 |
| JPS4922938B1 (OSRAM) | 1974-06-12 |
| CA926538A (en) | 1973-05-15 |
| NO121118B (OSRAM) | 1971-01-18 |
| DE1620823B2 (de) | 1978-10-26 |
| LU51210A1 (OSRAM) | 1968-02-21 |
| GB1155212A (en) | 1969-06-18 |
| BE691486A (OSRAM) | 1967-06-20 |
| AT313571B (de) | 1974-02-25 |
| BE694563A (OSRAM) | 1967-08-24 |
| DE1620823A1 (de) | 1970-06-18 |
| DE1620823C3 (de) | 1979-09-27 |
| JPS4922940B1 (OSRAM) | 1974-06-12 |
| SE362645B (OSRAM) | 1973-12-17 |
| CA926537A (en) | 1973-05-15 |
| NO126733B (OSRAM) | 1973-03-19 |
| CH477481A (fr) | 1969-08-31 |
| PH10758A (en) | 1977-09-02 |
| FR1500844A (fr) | 1967-11-10 |
| NL152283B (nl) | 1977-02-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |