CS274292B2 - Retader of double bond containing rubbers' vulcanization - Google Patents
Retader of double bond containing rubbers' vulcanization Download PDFInfo
- Publication number
- CS274292B2 CS274292B2 CS224687A CS224687A CS274292B2 CS 274292 B2 CS274292 B2 CS 274292B2 CS 224687 A CS224687 A CS 224687A CS 224687 A CS224687 A CS 224687A CS 274292 B2 CS274292 B2 CS 274292B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- sulfur
- vulcanization
- triazin
- mixture
- bis
- Prior art date
Links
- 238000004073 vulcanization Methods 0.000 title claims description 31
- 229920001971 elastomer Polymers 0.000 title claims description 20
- 239000005060 rubber Substances 0.000 title claims description 19
- 239000000203 mixture Chemical group 0.000 claims description 83
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 30
- 229910052717 sulfur Inorganic materials 0.000 claims description 27
- 239000011593 sulfur Chemical group 0.000 claims description 27
- -1 2-hydroxypropyl Chemical group 0.000 claims description 25
- 230000000694 effects Effects 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052739 hydrogen Chemical group 0.000 claims description 4
- 239000001257 hydrogen Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
- 239000004971 Cross linker Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 2
- 229940091173 hydantoin Drugs 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc oxide Inorganic materials [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 235000021355 Stearic acid Nutrition 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 11
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 11
- 239000008117 stearic acid Substances 0.000 description 11
- 239000011787 zinc oxide Substances 0.000 description 11
- FNGLQNMQHOAIJQ-UHFFFAOYSA-N Cl[S](Cl)Cl Chemical compound Cl[S](Cl)Cl FNGLQNMQHOAIJQ-UHFFFAOYSA-N 0.000 description 10
- 244000043261 Hevea brasiliensis Species 0.000 description 10
- OUBMGJOQLXMSNT-UHFFFAOYSA-N N-isopropyl-N'-phenyl-p-phenylenediamine Chemical compound C1=CC(NC(C)C)=CC=C1NC1=CC=CC=C1 OUBMGJOQLXMSNT-UHFFFAOYSA-N 0.000 description 10
- 238000004132 cross linking Methods 0.000 description 10
- 229920003052 natural elastomer Polymers 0.000 description 10
- 229920001194 natural rubber Polymers 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 230000001012 protector Effects 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 238000011534 incubation Methods 0.000 description 8
- MHKLKWCYGIBEQF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-ylsulfanyl)morpholine Chemical compound C1COCCN1SC1=NC2=CC=CC=C2S1 MHKLKWCYGIBEQF-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000006229 carbon black Substances 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229920000459 Nitrile rubber Polymers 0.000 description 4
- 238000007323 disproportionation reaction Methods 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000010059 sulfur vulcanization Methods 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- HAZJTCQWIDBCCE-UHFFFAOYSA-N 1h-triazine-6-thione Chemical compound SC1=CC=NN=N1 HAZJTCQWIDBCCE-UHFFFAOYSA-N 0.000 description 3
- HLBZWYXLQJQBKU-UHFFFAOYSA-N 4-(morpholin-4-yldisulfanyl)morpholine Chemical compound C1COCCN1SSN1CCOCC1 HLBZWYXLQJQBKU-UHFFFAOYSA-N 0.000 description 3
- FYWDACJBPKPKAQ-UHFFFAOYSA-N 6-[(4,6-diamino-1,3,5-triazin-2-yl)tetrasulfanyl]-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(SSSSC=2N=C(N)N=C(N)N=2)=N1 FYWDACJBPKPKAQ-UHFFFAOYSA-N 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000001469 hydantoins Chemical class 0.000 description 3
- CAXJFBOSFXRPOJ-UHFFFAOYSA-N n-phenyl-n-(trichloromethylsulfanyl)benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)N(SC(Cl)(Cl)Cl)C1=CC=CC=C1 CAXJFBOSFXRPOJ-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- GOUKSYJATNOEID-UHFFFAOYSA-N 2-(diethylamino)-6-(ethylamino)-1h-1,3,5-triazine-4-thione Chemical compound CCNC1=NC(=S)N=C(N(CC)CC)N1 GOUKSYJATNOEID-UHFFFAOYSA-N 0.000 description 2
- PRIMINIBLILXFO-UHFFFAOYSA-N 2-sulfanylidene-1-(trichloromethyl)imidazolidin-4-one Chemical compound ClC(Cl)(Cl)N1CC(=O)NC1=S PRIMINIBLILXFO-UHFFFAOYSA-N 0.000 description 2
- DHEKNWBRUYBLEX-UHFFFAOYSA-N 5-propan-2-yl-3-(trichloromethylsulfanyl)imidazolidine-2,4-dione Chemical compound CC(C)C1NC(=O)N(SC(Cl)(Cl)Cl)C1=O DHEKNWBRUYBLEX-UHFFFAOYSA-N 0.000 description 2
- CEPGTHZHEUKXNS-UHFFFAOYSA-N 5-propyl-3-(trichloromethylsulfanyl)imidazolidine-2,4-dione Chemical compound CCCC1NC(=O)N(SC(Cl)(Cl)Cl)C1=O CEPGTHZHEUKXNS-UHFFFAOYSA-N 0.000 description 2
- OLSFZHQVZYHPIM-UHFFFAOYSA-N 6-[(4,6-diamino-1,3,5-triazin-2-yl)disulfanyl]-1,3,5-triazine-2,4-diamine Chemical class NC1=NC(N)=NC(SSC=2N=C(N)N=C(N)N=2)=N1 OLSFZHQVZYHPIM-UHFFFAOYSA-N 0.000 description 2
- YJMUGCWPZVMLMP-UHFFFAOYSA-N 6-[[4-(diethylamino)-6-(ethylamino)-1,3,5-triazin-2-yl]disulfanyl]-2-n,2-n,4-n-triethyl-1,3,5-triazine-2,4-diamine Chemical compound CCN(CC)C1=NC(NCC)=NC(SSC=2N=C(N=C(NCC)N=2)N(CC)CC)=N1 YJMUGCWPZVMLMP-UHFFFAOYSA-N 0.000 description 2
- BWSLMOVFRHFYMA-UHFFFAOYSA-N 6-[[4-(diethylamino)-6-(ethylamino)-1,3,5-triazin-2-yl]tetrasulfanyl]-2-n,2-n,4-n-triethyl-1,3,5-triazine-2,4-diamine Chemical compound CCN(CC)C1=NC(NCC)=NC(SSSSC=2N=C(N=C(NCC)N=2)N(CC)CC)=N1 BWSLMOVFRHFYMA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229920005549 butyl rubber Polymers 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 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 2
- 150000002019 disulfides Chemical class 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229920003049 isoprene rubber Polymers 0.000 description 2
- 150000001282 organosilanes Chemical class 0.000 description 2
- UDKSLGIUCGAZTK-UHFFFAOYSA-N phenyl pentadecane-1-sulfonate Chemical compound CCCCCCCCCCCCCCCS(=O)(=O)OC1=CC=CC=C1 UDKSLGIUCGAZTK-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 230000000979 retarding effect Effects 0.000 description 2
- 150000004760 silicates Chemical class 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 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 2
- 239000001993 wax Substances 0.000 description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- FBPYJLYICYPYDV-UHFFFAOYSA-N 5,5-dimethyl-3-(trichloromethylsulfanyl)imidazolidine-2,4-dione Chemical compound CC1(C)NC(=O)N(SC(Cl)(Cl)Cl)C1=O FBPYJLYICYPYDV-UHFFFAOYSA-N 0.000 description 1
- DIBILXSXJLMVRM-UHFFFAOYSA-N 5-benzyl-3-(trichloromethylsulfanyl)imidazolidine-2,4-dione Chemical compound O=C1N(SC(Cl)(Cl)Cl)C(=O)NC1CC1=CC=CC=C1 DIBILXSXJLMVRM-UHFFFAOYSA-N 0.000 description 1
- RRBHLYNYLPWQMT-UHFFFAOYSA-N 5-propyl-1-(trichloromethylsulfanyl)imidazolidine-2,4-dione Chemical compound CCCC1N(SC(Cl)(Cl)Cl)C(=O)NC1=O RRBHLYNYLPWQMT-UHFFFAOYSA-N 0.000 description 1
- UYQZCNSMZZLBNL-UHFFFAOYSA-N 6-[(4,6-diamino-1,3,5-triazin-2-yl)sulfanyl]-1,3,5-triazine-2,4-diamine Chemical class NC1=NC(N)=NC(SC=2N=C(N)N=C(N)N=2)=N1 UYQZCNSMZZLBNL-UHFFFAOYSA-N 0.000 description 1
- MZHYLGKXDVVDLC-UHFFFAOYSA-N 6-[[4-(dipropylamino)-6-(ethylamino)-1,3,5-triazin-2-yl]tetrasulfanyl]-4-n-ethyl-2-n,2-n-dipropyl-1,3,5-triazine-2,4-diamine Chemical compound CCCN(CCC)C1=NC(NCC)=NC(SSSSC=2N=C(N=C(NCC)N=2)N(CCC)CCC)=N1 MZHYLGKXDVVDLC-UHFFFAOYSA-N 0.000 description 1
- ZYZPUADTBILLJU-UHFFFAOYSA-N 6-[[4-(dipropylamino)-6-(propylamino)-1,3,5-triazin-2-yl]tetrasulfanyl]-2-n,2-n,4-n-tripropyl-1,3,5-triazine-2,4-diamine Chemical compound CCCN(CCC)C1=NC(NCCC)=NC(SSSSC=2N=C(N=C(NCCC)N=2)N(CCC)CCC)=N1 ZYZPUADTBILLJU-UHFFFAOYSA-N 0.000 description 1
- PZVZQISVOUSPTJ-UHFFFAOYSA-N 6-[[4-[di(propan-2-yl)amino]-6-(propan-2-ylamino)-1,3,5-triazin-2-yl]disulfanyl]-2-n,2-n,4-n-tri(propan-2-yl)-1,3,5-triazine-2,4-diamine Chemical compound CC(C)N(C(C)C)C1=NC(NC(C)C)=NC(SSC=2N=C(N=C(NC(C)C)N=2)N(C(C)C)C(C)C)=N1 PZVZQISVOUSPTJ-UHFFFAOYSA-N 0.000 description 1
- XZSFGGZJICUUPA-UHFFFAOYSA-N 6-[[4-[di(propan-2-yl)amino]-6-(propan-2-ylamino)-1,3,5-triazin-2-yl]tetrasulfanyl]-2-n,2-n,4-n-tri(propan-2-yl)-1,3,5-triazine-2,4-diamine Chemical compound CC(C)N(C(C)C)C1=NC(NC(C)C)=NC(SSSSC=2N=C(N=C(NC(C)C)N=2)N(C(C)C)C(C)C)=N1 XZSFGGZJICUUPA-UHFFFAOYSA-N 0.000 description 1
- QYSADXBHSRXQPK-UHFFFAOYSA-N C(C)NN1NC(=CC(=N1)N(CC)CC)SSSSC1=CC(=NN(N1)NCC)N(CC)CC Chemical compound C(C)NN1NC(=CC(=N1)N(CC)CC)SSSSC1=CC(=NN(N1)NCC)N(CC)CC QYSADXBHSRXQPK-UHFFFAOYSA-N 0.000 description 1
- AHMOAKMQMSKVFM-UHFFFAOYSA-N C(C)NN1NC(=CC(=N1)N(CCCC)CCCC)S Chemical compound C(C)NN1NC(=CC(=N1)N(CCCC)CCCC)S AHMOAKMQMSKVFM-UHFFFAOYSA-N 0.000 description 1
- IJPQTEMDTZVVSA-UHFFFAOYSA-N C(CC)NN1NC(=CC(=N1)N(C(C)C)C(C)C)S Chemical compound C(CC)NN1NC(=CC(=N1)N(C(C)C)C(C)C)S IJPQTEMDTZVVSA-UHFFFAOYSA-N 0.000 description 1
- AYVVCEOCYWONRZ-UHFFFAOYSA-N C1(CCCCC1)NN1NC(=CC(=N1)N(CC)CC)S Chemical compound C1(CCCCC1)NN1NC(=CC(=N1)N(CC)CC)S AYVVCEOCYWONRZ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- ZNAZLWGLDYMLMJ-UHFFFAOYSA-N NN1NC(=CC(=N1)N)S Chemical class NN1NC(=CC(=N1)N)S ZNAZLWGLDYMLMJ-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 229920013648 Perbunan Polymers 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 102100036427 Spondin-2 Human genes 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- 239000006230 acetylene black Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000002929 anti-fatigue Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- UEZWYKZHXASYJN-UHFFFAOYSA-N cyclohexylthiophthalimide Chemical compound O=C1C2=CC=CC=C2C(=O)N1SC1CCCCC1 UEZWYKZHXASYJN-UHFFFAOYSA-N 0.000 description 1
- 229960002377 dixanthogen Drugs 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 150000002148 esters Chemical class 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
- 239000011888 foil Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000006233 lamp black Substances 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 108010074865 mindin Proteins 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- RYFZYYUIAZYQLC-UHFFFAOYSA-N perchloromethyl mercaptan Chemical compound ClSC(Cl)(Cl)Cl RYFZYYUIAZYQLC-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- GPNLWUFFWOYKLP-UHFFFAOYSA-N s-(1,3-benzothiazol-2-yl)thiohydroxylamine Chemical compound C1=CC=C2SC(SN)=NC2=C1 GPNLWUFFWOYKLP-UHFFFAOYSA-N 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 239000006234 thermal black Substances 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
- 150000003751 zinc Chemical class 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
- 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
- C08K5/45—Heterocyclic compounds having sulfur in the ring
- C08K5/46—Heterocyclic compounds having sulfur in the ring with oxygen or nitrogen in the ring
- C08K5/47—Thiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863610796 DE3610796A1 (de) | 1986-04-01 | 1986-04-01 | Verwendung von substituierten n-trichlormethylthiohydantoinen in kombination mit bis-(2,4-diamino-s-triazin-6-yl)-oligosulfiden in vulkanisierbaren kautschukmischungen und derartige kautschukmischungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS224687A2 CS224687A2 (en) | 1990-09-12 |
| CS274292B2 true CS274292B2 (en) | 1991-04-11 |
Family
ID=6297623
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS224687A CS274292B2 (en) | 1986-04-01 | 1987-03-31 | Retader of double bond containing rubbers' vulcanization |
| CS901284A CS275482B2 (en) | 1986-04-01 | 1987-03-31 | Curable masterbatch on rubber base that contains double bonds |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS901284A CS275482B2 (en) | 1986-04-01 | 1987-03-31 | Curable masterbatch on rubber base that contains double bonds |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0239813A3 (en)) |
| JP (1) | JPS62241936A (en)) |
| CN (1) | CN1010952B (en)) |
| AU (1) | AU589756B2 (en)) |
| BR (1) | BR8701446A (en)) |
| CS (2) | CS274292B2 (en)) |
| DE (1) | DE3610796A1 (en)) |
| DK (1) | DK160887A (en)) |
| FI (1) | FI871407A7 (en)) |
| HU (1) | HUT47616A (en)) |
| IL (1) | IL82008A (en)) |
| IN (1) | IN168931B (en)) |
| NO (1) | NO871198L (en)) |
| PL (1) | PL152859B1 (en)) |
| PT (1) | PT84602B (en)) |
| YU (1) | YU45407B (en)) |
| ZA (1) | ZA871768B (en)) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3610811A1 (de) * | 1986-04-01 | 1987-10-08 | Degussa | Verwendung von substituierten n-trichlormethylthiodicarboximiden in kombination mit n;n'-substituierten bis-(2,4-diamino-s-triazin-6-yl)-oligosulfiden in vulkanisierbaren kautschukmischungen und derartige kautschukmischungen |
| US4755320A (en) * | 1987-03-09 | 1988-07-05 | The Goodyear Tire & Rubber Company | Rubber vulcanization system |
| DE10017654A1 (de) * | 2000-04-08 | 2001-10-18 | Degussa | Organosiliciumverbindungen |
| EP2724870A1 (de) * | 2012-10-25 | 2014-04-30 | LANXESS Deutschland GmbH | Polysulfidmischungen, Verfahren zu ihrer Herstellung und Verwendung der Polysulfidmischungen in Kautschukmischungen |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1669954A1 (de) * | 1951-01-28 | 1970-08-20 | Degussa | Verfahren zur Verbesserung der Gebrauchseigenschaften von Vulkanisaten |
| US3546185A (en) * | 1968-03-20 | 1970-12-08 | Monsanto Co | Inhibiting premature vulcanization of diene rubbers |
| DE2848559C2 (de) * | 1978-11-09 | 1982-01-21 | Degussa Ag, 6000 Frankfurt | Reversionsfreie Vulkanisate ergebende Kautschukmischungen und deren Verwendung |
| US4380609A (en) * | 1981-10-19 | 1983-04-19 | Monsanto Company | Prevulcanization inhibitors of thio-triazine-amines for rubber |
| DE3610811A1 (de) * | 1986-04-01 | 1987-10-08 | Degussa | Verwendung von substituierten n-trichlormethylthiodicarboximiden in kombination mit n;n'-substituierten bis-(2,4-diamino-s-triazin-6-yl)-oligosulfiden in vulkanisierbaren kautschukmischungen und derartige kautschukmischungen |
| DE3610794C2 (de) * | 1986-04-01 | 1995-02-09 | Degussa | N,N'-substituierte Bis-(2,4-diamino-s-triazin-6-yl)-Tetrasulfide, Verfahren zu ihrer Herstellung und ihre Verwendung in vulkanisierbaren Kautschukmischungen |
-
1986
- 1986-04-01 DE DE19863610796 patent/DE3610796A1/de not_active Withdrawn
-
1987
- 1987-03-03 EP EP87102988A patent/EP0239813A3/de not_active Withdrawn
- 1987-03-09 YU YU382/87A patent/YU45407B/xx unknown
- 1987-03-10 IN IN193/CAL/87A patent/IN168931B/en unknown
- 1987-03-11 ZA ZA871768A patent/ZA871768B/xx unknown
- 1987-03-23 NO NO871198A patent/NO871198L/no unknown
- 1987-03-25 IL IL82008A patent/IL82008A/xx unknown
- 1987-03-27 AU AU70709/87A patent/AU589756B2/en not_active Ceased
- 1987-03-30 JP JP62074588A patent/JPS62241936A/ja active Pending
- 1987-03-30 BR BR8701446A patent/BR8701446A/pt unknown
- 1987-03-30 DK DK160887A patent/DK160887A/da not_active IP Right Cessation
- 1987-03-31 FI FI871407A patent/FI871407A7/fi not_active Application Discontinuation
- 1987-03-31 HU HU871388A patent/HUT47616A/hu unknown
- 1987-03-31 CS CS224687A patent/CS274292B2/cs unknown
- 1987-03-31 CS CS901284A patent/CS275482B2/cs unknown
- 1987-03-31 PL PL1987264913A patent/PL152859B1/pl unknown
- 1987-04-01 CN CN87102449A patent/CN1010952B/zh not_active Expired
- 1987-04-01 PT PT84602A patent/PT84602B/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PT84602B (pt) | 1989-11-30 |
| PL152859B1 (en) | 1991-02-28 |
| HUT47616A (en) | 1989-03-28 |
| AU589756B2 (en) | 1989-10-19 |
| CS9001284A3 (en) | 1992-02-19 |
| IN168931B (en)) | 1991-07-20 |
| CS224687A2 (en) | 1990-09-12 |
| CN1010952B (zh) | 1990-12-26 |
| JPS62241936A (ja) | 1987-10-22 |
| BR8701446A (pt) | 1988-01-05 |
| EP0239813A2 (de) | 1987-10-07 |
| CS275482B2 (en) | 1992-02-19 |
| YU45407B (en) | 1992-05-28 |
| NO871198D0 (no) | 1987-03-23 |
| IL82008A (en) | 1990-12-23 |
| CN87102449A (zh) | 1987-10-14 |
| IL82008A0 (en) | 1987-10-20 |
| DK160887A (da) | 1987-10-02 |
| FI871407A7 (fi) | 1987-10-02 |
| ZA871768B (en) | 1987-09-01 |
| FI871407A0 (fi) | 1987-03-31 |
| PL264913A1 (en) | 1988-07-21 |
| DE3610796A1 (de) | 1987-10-08 |
| DK160887D0 (da) | 1987-03-30 |
| PT84602A (de) | 1987-05-01 |
| AU7070987A (en) | 1987-10-08 |
| EP0239813A3 (de) | 1989-11-02 |
| YU38287A (en) | 1989-02-28 |
| NO871198L (no) | 1987-10-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2067974C1 (ru) | Сульфидсодержащие полицитраконимиды и полиитаконимиды | |
| CS274291B2 (en) | Retader of double bond containing rubbers' vulcanization | |
| US4621121A (en) | Vulcanizable mixture containing bis-(2-ethylamino-s-triazin-6-yl)-tetrasulfide | |
| US8546582B2 (en) | Sulfenamide, vulcanization accelerator containing the sulfenamide for rubber, and process for producing the vulcanization accelerator | |
| US3979369A (en) | Method for cross-linking rubber with polysulfides | |
| CS277646B6 (en) | N,n'-substituted bis-(2,4-diamino-s-triazin-6-yl)oligosulfides | |
| CS274292B2 (en) | Retader of double bond containing rubbers' vulcanization | |
| Trivette Jr et al. | Prevulcanization inhibitors | |
| JP2011527715A (ja) | 置換トリアジン組成物及びその製造方法 | |
| US5442099A (en) | Bis-(thiobenzoyldisulfido)-alkanes | |
| EP0078784B1 (en) | Thio-substituted-1,3,5-triazine-diamines and -triamines useful as prevulcanization inhibitors | |
| CZ9300779A3 (en) | Polycitraconimides and polyitacomides containing (poly)-sulfide groups | |
| US4673741A (en) | Bis-(2-ethylamino-4-diethylamino-s-triazine-6-yl) tetrasulfide, process for its production, use and vulcanizable mixtures containing it | |
| US3847880A (en) | Method for vulcanizing rubber with bis-sulfenamide accelerators | |
| US3969353A (en) | Triazinesulfenimides of dicarboxylic acids | |
| US5206304A (en) | Vulcanizable rubber mixtures containing bis-(2,4-organylthio-triazine-6-yl) polysulfides | |
| JPS59213745A (ja) | 加硫可能なゴム組成物 | |
| US4460769A (en) | Thio-amino-1,3,5-triazines | |
| US3872061A (en) | Diazacyclodiones | |
| US3770707A (en) | Nitrobenzothiazole alkyl or cycloalkyl disulfides | |
| JPH0245474A (ja) | ビス（２，４―オルガニルチオ―ｓ―トリアジン―６―イル）ポリスルフアン、その製法およびこれを含有する加硫可能な混合物 | |
| US3692770A (en) | 3-cycloalkylthio-3-azabicyclo (3.2.2) nonanes | |
| JPH03170473A (ja) | Ｓ―トリアジンスルフエンイミドの製法およびこれを加硫遅延剤として含有するゴム混合物 | |
| DD263297A5 (de) | Verwendung von substituierten N-Trichlormethylthiodicarboximiden in Kombination mit N,n'-Substituierten Bis-(2,4-Diamino-S-Triazin-6-yl)-oligosulfiden in vulkanisierbaren Kautschukmischungen und derartige Kautschukmischungen |