DE2502656C2 - Sulfenamide, deren Herstellung und Verwendung als Vulkanisationsverzögerer - Google Patents
Sulfenamide, deren Herstellung und Verwendung als VulkanisationsverzögererInfo
- Publication number
- DE2502656C2 DE2502656C2 DE2502656A DE2502656A DE2502656C2 DE 2502656 C2 DE2502656 C2 DE 2502656C2 DE 2502656 A DE2502656 A DE 2502656A DE 2502656 A DE2502656 A DE 2502656A DE 2502656 C2 DE2502656 C2 DE 2502656C2
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- phthalimide
- chloro
- sulfenamides
- chlorine
- 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 17
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000000460 chlorine Substances 0.000 claims description 29
- -1 cycloalkyl radicals Chemical group 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 13
- LTPQZFJAZILFME-UHFFFAOYSA-N 2-chloro-3-sulfanylideneisoindol-1-one Chemical compound C1=CC=C2C(=S)N(Cl)C(=O)C2=C1 LTPQZFJAZILFME-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 8
- 229920003052 natural elastomer Polymers 0.000 claims description 8
- 229920001194 natural rubber Polymers 0.000 claims description 8
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 229920003051 synthetic elastomer Polymers 0.000 claims description 5
- 239000005061 synthetic rubber Substances 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000002015 acyclic group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 31
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 15
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 12
- 229920001971 elastomer Polymers 0.000 description 12
- 239000005060 rubber Substances 0.000 description 12
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 8
- 150000001336 alkenes Chemical class 0.000 description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 5
- 150000001993 dienes Chemical class 0.000 description 5
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 244000043261 Hevea brasiliensis Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 150000001260 acyclic compounds Chemical class 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229940117389 dichlorobenzene Drugs 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- HIACAHMKXQESOV-UHFFFAOYSA-N 1,2-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC=C1C(C)=C HIACAHMKXQESOV-UHFFFAOYSA-N 0.000 description 2
- SWPXIEZUVOCINE-UHFFFAOYSA-N 1-dodecylcyclohexene Chemical compound CCCCCCCCCCCCC1=CCCCC1 SWPXIEZUVOCINE-UHFFFAOYSA-N 0.000 description 2
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 2
- CTMHWPIWNRWQEG-UHFFFAOYSA-N 1-methylcyclohexene Chemical compound CC1=CCCCC1 CTMHWPIWNRWQEG-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- XVJMNRIABVPIOU-UHFFFAOYSA-N 2-[(1,3-dioxoisoindol-2-yl)disulfanyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1SSN1C(=O)C2=CC=CC=C2C1=O XVJMNRIABVPIOU-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012320 chlorinating reagent Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000005673 monoalkenes Chemical class 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
- AVMHMVJVHYGDOO-NSCUHMNNSA-N (e)-1-bromobut-2-ene Chemical compound C\C=C\CBr AVMHMVJVHYGDOO-NSCUHMNNSA-N 0.000 description 1
- OPNUROKCUBTKLF-UHFFFAOYSA-N 1,2-bis(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1N\C(N)=N\C1=CC=CC=C1C OPNUROKCUBTKLF-UHFFFAOYSA-N 0.000 description 1
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- JPLZSSHKQZJYTJ-UHFFFAOYSA-N 2,2-dimethylhex-3-ene Chemical compound CCC=CC(C)(C)C JPLZSSHKQZJYTJ-UHFFFAOYSA-N 0.000 description 1
- WZUZDBPJFHQVJC-UHFFFAOYSA-N 2,3,4-trichlorobut-1-ene Chemical compound ClCC(Cl)C(Cl)=C WZUZDBPJFHQVJC-UHFFFAOYSA-N 0.000 description 1
- OWWIWYDDISJUMY-UHFFFAOYSA-N 2,3-dimethylbut-1-ene Chemical compound CC(C)C(C)=C OWWIWYDDISJUMY-UHFFFAOYSA-N 0.000 description 1
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical compound CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 1
- URRHKOYTHDCSDA-UHFFFAOYSA-N 2,5,8,11-tetramethyldodec-2-ene Chemical group CC(C)CCC(C)CCC(C)CC=C(C)C URRHKOYTHDCSDA-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- KZDCMKVLEYCGQX-UDPGNSCCSA-N 2-(diethylamino)ethyl 4-aminobenzoate;(2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;hydrate Chemical compound O.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1.N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 KZDCMKVLEYCGQX-UDPGNSCCSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 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 description 1
- OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-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
- USEGQJLHQSTGHW-UHFFFAOYSA-N 3-bromo-2-methylprop-1-ene Chemical compound CC(=C)CBr USEGQJLHQSTGHW-UHFFFAOYSA-N 0.000 description 1
- KLRGNKUMDFZCFE-UHFFFAOYSA-N 4-(2-chlorocyclohexyl)sulfanylisoindole-1,3-dione Chemical compound ClC1CCCCC1SC1=CC=CC2=C1C(=O)NC2=O KLRGNKUMDFZCFE-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- YKZUNWLMLRCVCW-UHFFFAOYSA-N 4-[2-(4-bicyclo[2.2.1]hept-2-enyl)ethyl]bicyclo[2.2.1]hept-2-ene Chemical compound C1CC(C2)C=CC21CCC1(C=C2)CC2CC1 YKZUNWLMLRCVCW-UHFFFAOYSA-N 0.000 description 1
- NWZJLSKAFZXSQH-UHFFFAOYSA-N 5,5-dimethylhex-2-ene Chemical compound CC=CCC(C)(C)C NWZJLSKAFZXSQH-UHFFFAOYSA-N 0.000 description 1
- DNKOOAMOMDGRIQ-UHFFFAOYSA-N 7-(1-chloro-2-methylpropan-2-yl)-3-sulfanylideneisoindol-1-one Chemical compound ClCC(C)(C)C1=CC=CC2=C1C(=O)NC2=S DNKOOAMOMDGRIQ-UHFFFAOYSA-N 0.000 description 1
- GDVIHNSKGZLQST-UHFFFAOYSA-N 7-(2-chloro-2-methylpropyl)-3-sulfanylideneisoindol-1-one Chemical compound CC(C)(Cl)CC1=CC=CC2=C1C(=O)NC2=S GDVIHNSKGZLQST-UHFFFAOYSA-N 0.000 description 1
- RQLGEIDVFNWXAA-UHFFFAOYSA-N 7-(2-chlorocyclobutyl)-3-sulfanylideneisoindol-1-one Chemical compound ClC1CCC1C1=CC=CC2=C1C(=O)NC2=S RQLGEIDVFNWXAA-UHFFFAOYSA-N 0.000 description 1
- QQSLAUIXGZQMMI-UHFFFAOYSA-N 7-(2-chlorocyclopentyl)-3-sulfanylideneisoindol-1-one Chemical compound ClC1CCCC1C1=CC=CC2=C1C(=O)NC2=S QQSLAUIXGZQMMI-UHFFFAOYSA-N 0.000 description 1
- ITCFNLGNCOVVKI-UHFFFAOYSA-N 7-(2-chloroethyl)-3-sulfanylideneisoindol-1-one Chemical compound ClCCC1=CC=CC2=C1C(=O)NC2=S ITCFNLGNCOVVKI-UHFFFAOYSA-N 0.000 description 1
- IXWGIBAHKLBLAU-UHFFFAOYSA-N 7-(2-chloropropyl)-3-sulfanylideneisoindol-1-one Chemical compound ClC(CC1=C2C(C(=S)NC2=O)=CC=C1)C IXWGIBAHKLBLAU-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 125000006414 CCl Chemical group ClC* 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- UBUCNCOMADRQHX-UHFFFAOYSA-N N-Nitrosodiphenylamine Chemical compound C=1C=CC=CC=1N(N=O)C1=CC=CC=C1 UBUCNCOMADRQHX-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical compound ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229930006739 camphene Natural products 0.000 description 1
- ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- 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 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- CCUHIMCZSDHBDP-UHFFFAOYSA-N diethylcarbamodithioic acid;zinc Chemical compound [Zn].CCN(CC)C(S)=S CCUHIMCZSDHBDP-UHFFFAOYSA-N 0.000 description 1
- CJSBUWDGPXGFGA-UHFFFAOYSA-N dimethyl-butadiene Natural products CC(C)=CC=C CJSBUWDGPXGFGA-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 150000004659 dithiocarbamates Chemical class 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000006232 furnace black Substances 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 125000005543 phthalimide group Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 150000003557 thiazoles 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- 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
- 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)
- Indole Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Plural Heterocyclic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2502656A DE2502656C2 (de) | 1975-01-23 | 1975-01-23 | Sulfenamide, deren Herstellung und Verwendung als Vulkanisationsverzögerer |
| GB44336/75A GB1528627A (en) | 1975-01-23 | 1975-10-28 | Sulphenamides their production and their use as vulcanisation retarders |
| IN2340/CAL/75A IN142932B (mber) | 1975-01-23 | 1975-12-15 | |
| US05/650,305 US4080399A (en) | 1975-01-23 | 1976-01-19 | Sulphenamides, their production and their use as vulcanization retarders |
| CA244,012A CA1071218A (en) | 1975-01-23 | 1976-01-21 | Sulphenamides, their production and their use as vulcanisation retarders |
| BE163685A BE837776A (fr) | 1975-01-23 | 1976-01-21 | Sulfenamides, leur preparation et leur utilisation comme retardateurs de vulcanisation |
| JP51005105A JPS5198271A (en) | 1975-01-23 | 1976-01-21 | ******no******* *su***te***ni*******ni*no* ********shi*e |
| IT47729/76A IT1053403B (it) | 1975-01-23 | 1976-01-21 | Solfenammidi e procedimento per la loro produzione ed applicazione |
| BR7600377A BR7600377A (pt) | 1975-01-23 | 1976-01-22 | Processo para a producao de sulfenamidas e composicoes retardadoras de vulcanizacao a base destas |
| NL7600670A NL7600670A (nl) | 1975-01-23 | 1976-01-22 | Sulfeenamiden en werkwijze voor het bereiden daarvan alsmede vulcanisatiesysteem en rubber. |
| ES444530A ES444530A1 (es) | 1975-01-23 | 1976-01-22 | Procedimiento para la obtencion de sulfenamidas. |
| FR7601873A FR2298540A1 (fr) | 1975-01-23 | 1976-01-23 | Sulfenamides, leur preparation et leur utilisation comme retardateurs de vulcanisation |
| ZA502A ZA76502B (en) | 1975-01-23 | 1976-01-29 | Sulphenamides their production and their use as volcanisation retarders |
| IN2288/CAL/76A IN145527B (mber) | 1975-01-23 | 1976-12-29 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2502656A DE2502656C2 (de) | 1975-01-23 | 1975-01-23 | Sulfenamide, deren Herstellung und Verwendung als Vulkanisationsverzögerer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2502656A1 DE2502656A1 (de) | 1976-08-05 |
| DE2502656C2 true DE2502656C2 (de) | 1982-06-24 |
Family
ID=5937108
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2502656A Expired DE2502656C2 (de) | 1975-01-23 | 1975-01-23 | Sulfenamide, deren Herstellung und Verwendung als Vulkanisationsverzögerer |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4080399A (mber) |
| JP (1) | JPS5198271A (mber) |
| BE (1) | BE837776A (mber) |
| BR (1) | BR7600377A (mber) |
| CA (1) | CA1071218A (mber) |
| DE (1) | DE2502656C2 (mber) |
| ES (1) | ES444530A1 (mber) |
| FR (1) | FR2298540A1 (mber) |
| GB (1) | GB1528627A (mber) |
| IN (2) | IN142932B (mber) |
| IT (1) | IT1053403B (mber) |
| NL (1) | NL7600670A (mber) |
| ZA (1) | ZA76502B (mber) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4879249A (en) * | 1983-02-25 | 1989-11-07 | Baldwin Thomas O | Linker compounds, linker-compound-ligands and linker-compound-receptors |
| RU2325377C2 (ru) * | 2006-07-24 | 2008-05-27 | Открытое акционерное общество "Химпром" | Способ получения n-(хлоралкилтио)фталимидов |
| RU2325376C2 (ru) * | 2006-07-24 | 2008-05-27 | Открытое акционерное общество "Химпром" | Способ выделения n-(хлоралкилтио) фталимидов из смеси с хлорбензолом |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2790749A (en) * | 1952-12-05 | 1957-04-30 | Tno | Nu-trichloromethylthio-4, 5-dimethyltetrahydrophthalimide and fungicidal composition containing same |
| NO121118B (mber) * | 1965-05-27 | 1971-01-18 | Monsanto Co | |
| DE1670705A1 (de) * | 1966-05-31 | 1970-11-12 | Bayer Ag | Verfahren zur Herstellung von N-substituierten Phthalimiden |
| US3586696A (en) * | 1969-02-25 | 1971-06-22 | Monsanto Co | (alkyl-,aralkyl-,and cycloalkylthio) arylenedicarboximides |
| BE755701A (fr) * | 1969-09-03 | 1971-03-03 | Bayer Ag | Procede de preparation de n-(4-chloro-phenylthiomethyl)- phtalimide |
| US3645987A (en) * | 1969-09-25 | 1972-02-29 | Monsanto Co | N-azolyl sulfenamides |
| DE2005692A1 (de) * | 1970-02-07 | 1971-08-26 | Farbenfabriken Bayer Aktiengesell schaft, 5090 Leverkusen | Vulkanisationsverzogerer |
| US3947429A (en) * | 1970-12-29 | 1976-03-30 | Sumitomo Chemical Company, Limited | Method for inhibiting premature vulcanization of diene rubbers |
-
1975
- 1975-01-23 DE DE2502656A patent/DE2502656C2/de not_active Expired
- 1975-10-28 GB GB44336/75A patent/GB1528627A/en not_active Expired
- 1975-12-15 IN IN2340/CAL/75A patent/IN142932B/en unknown
-
1976
- 1976-01-19 US US05/650,305 patent/US4080399A/en not_active Expired - Lifetime
- 1976-01-21 JP JP51005105A patent/JPS5198271A/ja active Pending
- 1976-01-21 IT IT47729/76A patent/IT1053403B/it active
- 1976-01-21 BE BE163685A patent/BE837776A/xx unknown
- 1976-01-21 CA CA244,012A patent/CA1071218A/en not_active Expired
- 1976-01-22 NL NL7600670A patent/NL7600670A/xx not_active Application Discontinuation
- 1976-01-22 BR BR7600377A patent/BR7600377A/pt unknown
- 1976-01-22 ES ES444530A patent/ES444530A1/es not_active Expired
- 1976-01-23 FR FR7601873A patent/FR2298540A1/fr active Granted
- 1976-01-29 ZA ZA502A patent/ZA76502B/xx unknown
- 1976-12-29 IN IN2288/CAL/76A patent/IN145527B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR7600377A (pt) | 1976-08-31 |
| GB1528627A (en) | 1978-10-18 |
| JPS5198271A (en) | 1976-08-30 |
| IN145527B (mber) | 1985-01-05 |
| CA1071218A (en) | 1980-02-05 |
| ZA76502B (en) | 1977-01-26 |
| FR2298540A1 (fr) | 1976-08-20 |
| IT1053403B (it) | 1981-08-31 |
| FR2298540B1 (mber) | 1980-06-27 |
| IN142932B (mber) | 1977-09-10 |
| ES444530A1 (es) | 1977-10-01 |
| NL7600670A (nl) | 1976-07-27 |
| DE2502656A1 (de) | 1976-08-05 |
| BE837776A (fr) | 1976-07-22 |
| US4080399A (en) | 1978-03-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2045574C3 (de) | Schwefelvulkanisierbare Masse | |
| EP0709401B1 (de) | Verfahren zur Bromierung von Alkylkautschuken | |
| EP0191929A1 (de) | Haftvermittler zur Herstellung von Vulkanisaten mit gutem Füllstoff/Kautschuk-Verbund | |
| DE2502656C2 (de) | Sulfenamide, deren Herstellung und Verwendung als Vulkanisationsverzögerer | |
| DE3853841T2 (de) | Nichtfleckenbildende und wenigfleckenbildende Ozon-Schutzmittel. | |
| DE1543648B1 (de) | Verfahren zur Herstellung von Chlorierungsprodukten der Dichlor-9-thiabicyclononane | |
| DE1076692B (de) | Verfahren zur Herstellung von N-Alkyl- und N-Cycloalkyl-bis-(2-benzothiazolsulfen)-amiden | |
| DE2708190A1 (de) | M-brom-benzotrifluoride | |
| DE2105030C3 (de) | Verfahren zur Herstellung von Amidoalkansulfonsäuren | |
| CH627443A5 (de) | Verfahren zur herstellung von acylcyaniden. | |
| EP0001276B1 (de) | Verfahren zur Herstellung von Sulfonsäurechloriden | |
| DE3686167T2 (de) | Oligomere aminierte und phenolische inhibitoren. | |
| DE69706114T2 (de) | Verfahren zur Herstellung von 3-Piperazinylisothiazolen | |
| DE1620406A1 (de) | Basisch substituierte Adamantyl-2,3-di-hydro-1,5-benzthiazepinone und Verfahren zu ihrer Herstellung | |
| DE2943433A1 (de) | Verfahren zur herstellung von carbonsaeurehalogeniden | |
| DE2721429C2 (mber) | ||
| EP0172481A1 (de) | Alterungsschutzmittel und diese enthaltende Polymere | |
| DE2324981C2 (de) | Thiocarbamylsulfenamide | |
| DE1494199C3 (de) | p-Nitrosoanilin-Derivate und deren Verwendung als Vulkanisationshilfsmittel für verstärkten Naturkautschuk, Homo- und Mischpolymerisaten von Dienkohlenwasserstoffe!!, Butylkautschuk und deren Gemischen | |
| EP0544074A1 (de) | Verfahren zur Herstellung von ortho-substituierten Alkylphenolen und Katalysator hierfür | |
| DE2551504A1 (de) | Sulfenamide, deren herstellung sowie deren verwendung als vulkanisationsverzoegerer | |
| EP0967230B1 (de) | Katalysatorsystem zur Herstellung von Olefin(co)polymerisaten | |
| DE932964C (de) | Verfahren zur Herstellung von ª‡,ª‰-ungesaettigten Carbonsaeureamiden aus ª‰-Halogencarbonsaeureamiden | |
| DE2150095A1 (de) | Phenolverbindungen | |
| DE1253704B (de) | Verfahren zur Herstellung ungesaettigter Carbonsaeurenitrile |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |