SK149894A3 - 3-pyradizine derivatives and their use in rubbers - Google Patents

3-pyradizine derivatives and their use in rubbers Download PDF

Info

Publication number: SK149894A3
Authority: SK; Slovakia
Prior art keywords: parts; composition according; weight; compound; rubber
Prior art date: 1992-06-05

Application number

SK1498-94A

Other languages

English (en)

Slovak (sk)

Inventor

Horng-Jau Lin

Charles J Rostek Jr

David J Sikora

Original Assignee

Monsanto Co

Priority date (The priority date 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 date listed.)

1992-06-05

Filing date

1993-05-14

Publication date

1995-07-11

1993-05-14 Application filed by Monsanto Co filed Critical Monsanto Co

1995-07-11 Publication of SK149894A3 publication Critical patent/SK149894A3/sk

Links

229920001971 elastomer Polymers 0.000 title claims abstract description 29
239000005060 rubber Substances 0.000 title claims abstract description 29
150000001875 compounds Chemical class 0.000 claims abstract description 46
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 abstract description 9
239000000203 mixture Substances 0.000 claims description 68
-1 3-pyridazyl Chemical group 0.000 claims description 23
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
239000011593 sulfur Substances 0.000 claims description 15
229910052717 sulfur Inorganic materials 0.000 claims description 15
125000001424 substituent group Chemical group 0.000 claims description 10
125000000623 heterocyclic group Chemical group 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 7
239000003963 antioxidant agent Substances 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
230000003078 antioxidant effect Effects 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
VWJMLKZDVPDMIN-UHFFFAOYSA-N n-pyridazin-3-ylsulfanylcyclohexanamine Chemical compound C1CCCCC1NSC1=CC=CN=N1 VWJMLKZDVPDMIN-UHFFFAOYSA-N 0.000 claims description 3
GUNLDGUMBCJARF-UHFFFAOYSA-N n-pyridazin-3-ylsulfanylpropan-2-amine Chemical compound CC(C)NSC1=CC=CN=N1 GUNLDGUMBCJARF-UHFFFAOYSA-N 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
IBWYHNOFSKJKKY-UHFFFAOYSA-N 3-chloropyridazine Chemical compound ClC1=CC=CN=N1 IBWYHNOFSKJKKY-UHFFFAOYSA-N 0.000 claims description 2
150000001768 cations Chemical class 0.000 claims description 2
125000002877 alkyl aryl group Chemical group 0.000 claims 2
BYLOHCRAPOSXLY-UHFFFAOYSA-N dichloro(diethyl)silane Chemical compound CC[Si](Cl)(Cl)CC BYLOHCRAPOSXLY-UHFFFAOYSA-N 0.000 claims 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
PWTGMMGMJNWFLX-UHFFFAOYSA-N 2-methyl-n-pyridazin-3-ylsulfanylpropan-2-amine Chemical compound CC(C)(C)NSC1=CC=CN=N1 PWTGMMGMJNWFLX-UHFFFAOYSA-N 0.000 claims 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 claims 1
238000004073 vulcanization Methods 0.000 abstract description 42
150000003573 thiols Chemical class 0.000 abstract description 13
150000002019 disulfides Chemical class 0.000 abstract description 10
150000004892 pyridazines Chemical class 0.000 abstract 1
238000010059 sulfur vulcanization Methods 0.000 abstract 1
229920003052 natural elastomer Polymers 0.000 description 23
229920001194 natural rubber Polymers 0.000 description 23
229920003048 styrene butadiene rubber Polymers 0.000 description 22
244000043261 Hevea brasiliensis Species 0.000 description 21
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YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 16
241001441571 Hiodontidae Species 0.000 description 15
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239000005061 synthetic rubber Substances 0.000 description 14
229920002943 EPDM rubber Polymers 0.000 description 13
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 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
229920000459 Nitrile rubber Polymers 0.000 description 10
239000000047 product Substances 0.000 description 10
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 10
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XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
229910052799 carbon Inorganic materials 0.000 description 7
238000000034 method Methods 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
239000005708 Sodium hypochlorite Substances 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
239000006229 carbon black Substances 0.000 description 6
150000001993 dienes Chemical class 0.000 description 6
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 6
235000021355 Stearic acid Nutrition 0.000 description 5
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 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
150000003839 salts Chemical class 0.000 description 5
239000008117 stearic acid Substances 0.000 description 5
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 5
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BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
229920001577 copolymer Polymers 0.000 description 4
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
230000010354 integration Effects 0.000 description 4
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 4
239000003921 oil Substances 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000011787 zinc oxide Substances 0.000 description 4
YQQSRZSUGBETRS-UHFFFAOYSA-N 1h-pyridazine-6-thione Chemical compound SC1=CC=CN=N1 YQQSRZSUGBETRS-UHFFFAOYSA-N 0.000 description 3
ABQHEWLZYZQXHY-UHFFFAOYSA-N 3-chloro-1h-pyridazine-6-thione Chemical compound SC1=CC=C(Cl)N=N1 ABQHEWLZYZQXHY-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
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
239000005062 Polybutadiene Substances 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 3
229920002857 polybutadiene Polymers 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
238000013040 rubber vulcanization Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000012360 testing method Methods 0.000 description 3
BOGRNZQRTNVZCZ-UHFFFAOYSA-N 1,2-dimethyl-butadiene Natural products CC=C(C)C=C BOGRNZQRTNVZCZ-UHFFFAOYSA-N 0.000 description 2
OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 2
RCJMVGJKROQDCB-UHFFFAOYSA-N 2-methylpenta-1,3-diene Chemical compound CC=CC(C)=C RCJMVGJKROQDCB-UHFFFAOYSA-N 0.000 description 2
KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
RLRVNXHSMJOYMU-UHFFFAOYSA-N 3-(tert-butylamino)sulfanyl-1h-pyridazin-6-one Chemical compound CC(C)(C)NSC=1C=CC(=O)NN=1 RLRVNXHSMJOYMU-UHFFFAOYSA-N 0.000 description 2
SRYILVFXQKHDGZ-UHFFFAOYSA-N 6-sulfanylidene-1,2-dihydropyridazin-3-one Chemical compound OC1=CC=C(S)N=N1 SRYILVFXQKHDGZ-UHFFFAOYSA-N 0.000 description 2
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
239000004594 Masterbatch (MB) Substances 0.000 description 2
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CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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150000001491 aromatic compounds Chemical class 0.000 description 2
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239000012065 filter cake Substances 0.000 description 2
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238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
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229920006395 saturated elastomer Polymers 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
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238000010561 standard procedure Methods 0.000 description 2
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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
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HPFHYRNETZEPIV-UHFFFAOYSA-N (piperidine-1-carbothioylpentasulfanyl) piperidine-1-carbodithioate Chemical compound C1CCCCN1C(=S)SSSSSSC(=S)N1CCCCC1 HPFHYRNETZEPIV-UHFFFAOYSA-N 0.000 description 1
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-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
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WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 1
GUSWJGOYDXFJSI-UHFFFAOYSA-N 3,6-dichloropyridazine Chemical compound ClC1=CC=C(Cl)N=N1 GUSWJGOYDXFJSI-UHFFFAOYSA-N 0.000 description 1
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125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
HKJUZDZYRIBHPW-UHFFFAOYSA-N 4,5-dimethylocta-1,3-diene Chemical compound CCCC(C)C(C)=CC=C HKJUZDZYRIBHPW-UHFFFAOYSA-N 0.000 description 1
MHKLKWCYGIBEQF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-ylsulfanyl)morpholine Chemical compound C1COCCN1SC1=NC2=CC=CC=C2S1 MHKLKWCYGIBEQF-UHFFFAOYSA-N 0.000 description 1
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
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AULWPXHFRBLPAE-UHFFFAOYSA-N 6-chloropyridine Chemical compound ClC1=C=CC=C[N]1 AULWPXHFRBLPAE-UHFFFAOYSA-N 0.000 description 1
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HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
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239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000012190 activator Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
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125000000129 anionic group Chemical group 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
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125000003118 aryl group Chemical group 0.000 description 1
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XZKRXPZXQLARHH-UHFFFAOYSA-N buta-1,3-dienylbenzene Chemical compound C=CC=CC1=CC=CC=C1 XZKRXPZXQLARHH-UHFFFAOYSA-N 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
125000006309 butyl amino group Chemical group 0.000 description 1
229920005549 butyl rubber Polymers 0.000 description 1
CSNJTIWCTNEOSW-UHFFFAOYSA-N carbamothioylsulfanyl carbamodithioate Chemical compound NC(=S)SSC(N)=S CSNJTIWCTNEOSW-UHFFFAOYSA-N 0.000 description 1
229920005556 chlorobutyl Polymers 0.000 description 1
239000004927 clay Substances 0.000 description 1
229910052570 clay Inorganic materials 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
230000003247 decreasing effect Effects 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
WITDFSFZHZYQHB-UHFFFAOYSA-N dibenzylcarbamothioylsulfanyl n,n-dibenzylcarbamodithioate Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)C(=S)SSC(=S)N(CC=1C=CC=CC=1)CC1=CC=CC=C1 WITDFSFZHZYQHB-UHFFFAOYSA-N 0.000 description 1
PGAXJQVAHDTGBB-UHFFFAOYSA-N dibutylcarbamothioylsulfanyl n,n-dibutylcarbamodithioate Chemical compound CCCCN(CCCC)C(=S)SSC(=S)N(CCCC)CCCC PGAXJQVAHDTGBB-UHFFFAOYSA-N 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 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
XTJLXXCARCJVPJ-UHFFFAOYSA-N hepta-2,4-diene Chemical compound CCC=CC=CC XTJLXXCARCJVPJ-UHFFFAOYSA-N 0.000 description 1
AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000000178 monomer Substances 0.000 description 1
CMAUJSNXENPPOF-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)-n-cyclohexylcyclohexanamine Chemical compound C1CCCCC1N(C1CCCCC1)SC1=NC2=CC=CC=C2S1 CMAUJSNXENPPOF-UHFFFAOYSA-N 0.000 description 1
AVLRJVPAKJCVMC-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)butan-1-amine Chemical compound C1=CC=C2SC(SNCCCC)=NC2=C1 AVLRJVPAKJCVMC-UHFFFAOYSA-N 0.000 description 1
229940032017 n-oxydiethylene-2-benzothiazole sulfenamide Drugs 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000012744 reinforcing agent Substances 0.000 description 1
AQHBWWRHIPVRBT-UHFFFAOYSA-N s-(1,3-thiazol-2-yl)thiohydroxylamine Chemical class NSC1=NC=CS1 AQHBWWRHIPVRBT-UHFFFAOYSA-N 0.000 description 1
VRGDYOBGAIMYLQ-UHFFFAOYSA-N s-(4-propan-2-yl-1,3-benzothiazol-2-yl)thiohydroxylamine Chemical compound CC(C)C1=CC=CC2=C1N=C(SN)S2 VRGDYOBGAIMYLQ-UHFFFAOYSA-N 0.000 description 1
BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000003497 tellurium Chemical class 0.000 description 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000003557 thiazoles Chemical class 0.000 description 1
150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
WOAQZEHJXZOJCS-UHFFFAOYSA-N zinc;diisocyanate Chemical class [Zn+2].[N-]=C=O.[N-]=C=O WOAQZEHJXZOJCS-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
- C08K5/37—Thiols
- C08K5/378—Thiols containing heterocyclic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
- C07D237/18—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3462—Six-membered rings
- 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
- C08K5/37—Thiols
- 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)

SK1498-94A 1992-06-05 1993-05-14 3-pyradizine derivatives and their use in rubbers SK149894A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US89467792A	1992-06-05	1992-06-05
US5397193A	1993-05-04	1993-05-04
PCT/US1993/004647 WO1993025537A1 (en)	1992-06-05	1993-05-14	3-pyridazine derivatives and their use in rubber

Publications (1)

Publication Number	Publication Date
SK149894A3 true SK149894A3 (en)	1995-07-11

Family

ID=26732444

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1498-94A SK149894A3 (en)	1992-06-05	1993-05-14	3-pyradizine derivatives and their use in rubbers

Country Status (13)

Country	Link
EP (2)	EP0726255A3 (cs)
JP (1)	JPH07507561A (cs)
KR (1)	KR950701914A (cs)
CN (1)	CN1085227A (cs)
AT (1)	ATE156122T1 (cs)
AU (1)	AU670438B2 (cs)
BR (1)	BR9306494A (cs)
CA (1)	CA2135494A1 (cs)
CZ (1)	CZ289894A3 (cs)
DE (1)	DE69312715T2 (cs)
SK (1)	SK149894A3 (cs)
TW (1)	TW260687B (cs)
WO (1)	WO1993025537A1 (cs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2951167B1 (fr) *	2009-10-08	2011-10-28	Michelin Soc Tech	1,2,4-triazine utilisable comme accelerateur de vulcanisation et son procede d'obtention
CN118994743B (zh) *	2024-09-10	2026-03-06	华南理工大学	一种快速硫化橡胶组合物及其制备方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2382769A (en) *	1942-06-20	1945-08-14	Us Rubber Co	Vulcanization accelerators
CA992965A (en) *	1971-02-08	1976-07-13	John W. Fieldhouse	Diazine, triazine, pyridine, quinoline sulfenamides and their manufacture
JPS58125733A (ja) *	1982-01-22	1983-07-26	Oouchi Shinko Kagaku Kogyo Kk	クロロプレンゴム加硫組成物

1993
- 1993-05-14 WO PCT/US1993/004647 patent/WO1993025537A1/en not_active Ceased
- 1993-05-14 KR KR1019940704417A patent/KR950701914A/ko not_active Ceased
- 1993-05-14 JP JP6501476A patent/JPH07507561A/ja active Pending
- 1993-05-14 SK SK1498-94A patent/SK149894A3/sk unknown
- 1993-05-14 AT AT93911338T patent/ATE156122T1/de not_active IP Right Cessation
- 1993-05-14 EP EP96104311A patent/EP0726255A3/en not_active Withdrawn
- 1993-05-14 CZ CZ942898A patent/CZ289894A3/cs unknown
- 1993-05-14 BR BR9306494A patent/BR9306494A/pt not_active Application Discontinuation
- 1993-05-14 AU AU42510/93A patent/AU670438B2/en not_active Ceased
- 1993-05-14 CA CA002135494A patent/CA2135494A1/en not_active Abandoned
- 1993-05-14 DE DE69312715T patent/DE69312715T2/de not_active Expired - Fee Related
- 1993-05-14 EP EP93911338A patent/EP0644881B1/en not_active Expired - Lifetime
- 1993-06-04 CN CN93108226A patent/CN1085227A/zh active Pending
- 1993-06-04 TW TW082104477A patent/TW260687B/zh active

Also Published As

Publication number	Publication date
EP0644881A1 (en)	1995-03-29
AU670438B2 (en)	1996-07-18
AU4251093A (en)	1994-01-04
EP0644881B1 (en)	1997-07-30
EP0726255A2 (en)	1996-08-14
CA2135494A1 (en)	1993-12-23
EP0726255A3 (en)	1997-03-26
DE69312715T2 (de)	1998-01-29
CZ289894A3 (en)	1995-04-12
WO1993025537A1 (en)	1993-12-23
DE69312715D1 (de)	1997-09-04
ATE156122T1 (de)	1997-08-15
TW260687B (cs)	1995-10-21
CN1085227A (zh)	1994-04-13
BR9306494A (pt)	1998-09-15
KR950701914A (ko)	1995-05-17
JPH07507561A (ja)	1995-08-24

Publication	Publication Date	Title
US4621121A (en)	1986-11-04	Vulcanizable mixture containing bis-(2-ethylamino-s-triazin-6-yl)-tetrasulfide
US5374689A (en)	1994-12-20	Rubber compositions containing 2-pyrazine sulfenamides
EP0417057A2 (en)	1991-03-13	Heterocyclic thiol-based sulfenimide compounds and rubber compositions containing them
US4687756A (en)	1987-08-18	Vulcanization accelerator, a means for accelerating vulcanization and an improved rubber product containing said accelerator therein
SK149894A3 (en)	1995-07-11	3-pyradizine derivatives and their use in rubbers
EP0643702B1 (en)	1997-01-02	4-pyrimidine sulfenamides and their use in rubber
US4873291A (en)	1989-10-10	Rubber vulcanization system with triazine compounds
US3778419A (en)	1973-12-11	Vulcanization process with s,s'-carbonyl-bis-dialkyldithiophosphate
US4673741A (en)	1987-06-16	Bis-(2-ethylamino-4-diethylamino-s-triazine-6-yl) tetrasulfide, process for its production, use and vulcanizable mixtures containing it
US2691015A (en)	1954-10-05	N-(4-thiazolinyl-2) sulfenimides
EP0282434A1 (en)	1988-09-14	Rubber vulcanization system
US4808666A (en)	1989-02-28	Rubber vulcanization system
CA2193900A1 (en)	1991-03-06	Heterocyclic thiol sulfenimide compounds