DD284007A5 - Verfahren zur herstellung von gemischen, bestehend aus n,n'-substituierter bis-(2,4-diamino-s-triakin-6-yl)-oligo-sulfiden - Google Patents
Verfahren zur herstellung von gemischen, bestehend aus n,n'-substituierter bis-(2,4-diamino-s-triakin-6-yl)-oligo-sulfiden Download PDFInfo
- Publication number
- DD284007A5 DD284007A5 DD87328211A DD32821187A DD284007A5 DD 284007 A5 DD284007 A5 DD 284007A5 DD 87328211 A DD87328211 A DD 87328211A DD 32821187 A DD32821187 A DD 32821187A DD 284007 A5 DD284007 A5 DD 284007A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- rubber
- parts
- sulfur
- mixtures
- diamino
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 91
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 title description 97
- 150000003568 thioethers Chemical class 0.000 title 1
- 229920001971 elastomer Polymers 0.000 claims abstract description 55
- 239000005060 rubber Substances 0.000 claims abstract description 54
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 43
- 239000011593 sulfur Substances 0.000 claims abstract description 42
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 239000000945 filler Substances 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 11
- 239000000470 constituent Substances 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 235000012239 silicon dioxide Nutrition 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005624 silicic acid group Chemical class 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 2
- 229910052782 aluminium Inorganic materials 0.000 claims 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims 1
- 241001476763 Einara Species 0.000 claims 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims 1
- 239000005642 Oleic acid Substances 0.000 claims 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 238000004073 vulcanization Methods 0.000 abstract description 30
- 229920001194 natural rubber Polymers 0.000 abstract description 22
- 229920003052 natural elastomer Polymers 0.000 abstract description 21
- 238000002360 preparation method Methods 0.000 abstract description 6
- 229920003051 synthetic elastomer Polymers 0.000 abstract description 4
- 239000005061 synthetic rubber Substances 0.000 abstract description 4
- -1 2,4-diamino-s-triazine-6-yl Chemical group 0.000 description 47
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- 244000043261 Hevea brasiliensis Species 0.000 description 19
- 150000004763 sulfides Chemical class 0.000 description 17
- 235000021355 Stearic acid Nutrition 0.000 description 15
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 15
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 15
- 239000008117 stearic acid Substances 0.000 description 15
- 238000004132 cross linking Methods 0.000 description 14
- 230000001012 protector Effects 0.000 description 14
- 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 12
- 235000019241 carbon black Nutrition 0.000 description 12
- 239000006229 carbon black Substances 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 9
- 239000004971 Cross linker Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000010059 sulfur vulcanization 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229920002857 polybutadiene Polymers 0.000 description 6
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 5
- 239000005062 Polybutadiene Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000007323 disproportionation reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000011534 incubation Methods 0.000 description 5
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- 238000013021 overheating Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 150000001282 organosilanes Chemical class 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 150000004760 silicates Chemical class 0.000 description 4
- 229920003048 styrene butadiene rubber Polymers 0.000 description 4
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 4
- HAZJTCQWIDBCCE-UHFFFAOYSA-N 1h-triazine-6-thione Chemical compound SC1=CC=NN=N1 HAZJTCQWIDBCCE-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 class NC1=NC(N)=NC(SSSSC=2N=C(N)N=C(N)N=2)=N1 FYWDACJBPKPKAQ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229920002943 EPDM rubber Polymers 0.000 description 3
- 229920000459 Nitrile rubber Polymers 0.000 description 3
- 239000002174 Styrene-butadiene Substances 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- HLBZWYXLQJQBKU-UHFFFAOYSA-N 4-(morpholin-4-yldisulfanyl)morpholine Chemical compound C1COCCN1SSN1CCOCC1 HLBZWYXLQJQBKU-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- UEZWYKZHXASYJN-UHFFFAOYSA-N cyclohexylthiophthalimide Chemical compound O=C1C2=CC=CC=C2C(=O)N1SC1CCCCC1 UEZWYKZHXASYJN-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 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 2
- 229920001195 polyisoprene Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- GPNLWUFFWOYKLP-UHFFFAOYSA-N s-(1,3-benzothiazol-2-yl)thiohydroxylamine Chemical class C1=CC=C2SC(SN)=NC2=C1 GPNLWUFFWOYKLP-UHFFFAOYSA-N 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229960002447 thiram Drugs 0.000 description 2
- VNDRMZTXEFFQDR-UHFFFAOYSA-N (piperidine-1-carbothioyltrisulfanyl) piperidine-1-carbodithioate Chemical compound C1CCCCN1C(=S)SSSSC(=S)N1CCCCC1 VNDRMZTXEFFQDR-UHFFFAOYSA-N 0.000 description 1
- SDYMYAFSQACTQP-UHFFFAOYSA-N 1,3-benzothiazole-2-sulfonamide Chemical compound C1=CC=C2SC(S(=O)(=O)N)=NC2=C1 SDYMYAFSQACTQP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 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
- CPGFMWPQXUXQRX-UHFFFAOYSA-N 3-amino-3-(4-fluorophenyl)propanoic acid Chemical compound OC(=O)CC(N)C1=CC=C(F)C=C1 CPGFMWPQXUXQRX-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 241000282619 Hylobates lar Species 0.000 description 1
- SSIZMDFYGQDVCI-UHFFFAOYSA-N N-morpholin-4-ylsulfanyl-1,3-benzothiazol-2-amine Chemical compound C1COCCN1SNC1=NC2=CC=CC=C2S1 SSIZMDFYGQDVCI-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
- 241000872198 Serjania polyphylla Species 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- IDCBOTIENDVCBQ-UHFFFAOYSA-N TEPP Chemical compound CCOP(=O)(OCC)OP(=O)(OCC)OCC IDCBOTIENDVCBQ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000032683 aging Effects 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
- 125000000217 alkyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 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
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012455 biphasic mixture Substances 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000003431 cross linking reagent Substances 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
- 230000006735 deficit 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
- REQPQFUJGGOFQL-UHFFFAOYSA-N dimethylcarbamothioyl n,n-dimethylcarbamodithioate Chemical compound CN(C)C(=S)SC(=S)N(C)C REQPQFUJGGOFQL-UHFFFAOYSA-N 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 229960002377 dixanthogen Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 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
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
- 239000011888 foil Substances 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
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- OFHMODDLBXETIK-UHFFFAOYSA-N methyl 2,3-dichloropropanoate Chemical compound COC(=O)C(Cl)CCl OFHMODDLBXETIK-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- 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 1
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 1
- 150000004005 nitrosamines Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- UDKSLGIUCGAZTK-UHFFFAOYSA-N phenyl pentadecane-1-sulfonate Chemical compound CCCCCCCCCCCCCCCS(=O)(=O)OC1=CC=CC=C1 UDKSLGIUCGAZTK-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010057 rubber processing Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/48—Two nitrogen atoms
- C07D251/52—Two nitrogen atoms with an oxygen or sulfur atom attached to the third ring carbon atom
-
- 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
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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3610794A DE3610794C2 (de) | 1986-04-01 | 1986-04-01 | N,N'-substituierte Bis-(2,4-diamino-s-triazin-6-yl)-Tetrasulfide, Verfahren zu ihrer Herstellung und ihre Verwendung in vulkanisierbaren Kautschukmischungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD284007A5 true DD284007A5 (de) | 1990-10-31 |
Family
ID=6297621
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD87328211A DD284007A5 (de) | 1986-04-01 | 1987-03-31 | Verfahren zur herstellung von gemischen, bestehend aus n,n'-substituierter bis-(2,4-diamino-s-triakin-6-yl)-oligo-sulfiden |
| DD30132387A DD270302A5 (de) | 1986-04-01 | 1987-03-31 | N,n'-Substituierte Bis-(2,4-Diamino-S-triazin-6-yl)-tetra-sulfide und ihre Disproportionierungsprodukte, Verfahren zu ihrer Herstellung und ihre Verwendung in vulkanisierbaren Kautschukmischungen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD30132387A DD270302A5 (de) | 1986-04-01 | 1987-03-31 | N,n'-Substituierte Bis-(2,4-Diamino-S-triazin-6-yl)-tetra-sulfide und ihre Disproportionierungsprodukte, Verfahren zu ihrer Herstellung und ihre Verwendung in vulkanisierbaren Kautschukmischungen |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0239816B1 (en, 2012) |
| JP (1) | JPS62240672A (en, 2012) |
| CN (2) | CN87102447A (en, 2012) |
| AT (1) | ATE105552T1 (en, 2012) |
| AU (1) | AU591249B2 (en, 2012) |
| BR (1) | BR8701445A (en, 2012) |
| CA (1) | CA1325805C (en, 2012) |
| CS (2) | CS276589B6 (en, 2012) |
| DD (2) | DD284007A5 (en, 2012) |
| DE (2) | DE3610794C2 (en, 2012) |
| DK (1) | DK160987A (en, 2012) |
| FI (1) | FI871409A7 (en, 2012) |
| HU (1) | HU205918B (en, 2012) |
| IN (3) | IN169093B (en, 2012) |
| NO (1) | NO871194L (en, 2012) |
| PL (1) | PL158593B1 (en, 2012) |
| PT (1) | PT84606B (en, 2012) |
| YU (3) | YU46045B (en, 2012) |
| ZA (1) | ZA871769B (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3438290A1 (de) * | 1984-10-19 | 1986-04-24 | Degussa Ag, 6000 Frankfurt | Bis-(2-ethylamino-4-diethylamino-s-triazin-6- yl)tetrasulfid,verfahren zur herstellung, verwendung und sie enthaltende vulkanisierbare mischungen |
| 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 |
| DE3610796A1 (de) * | 1986-04-01 | 1987-10-08 | Degussa | Verwendung von substituierten n-trichlormethylthiohydantoinen in kombination mit bis-(2,4-diamino-s-triazin-6-yl)-oligosulfiden in vulkanisierbaren kautschukmischungen und derartige kautschukmischungen |
| DE3630055C2 (de) * | 1986-09-04 | 1997-04-10 | Swan Thomas & Co Ltd | Verfahren zur Herstellung schwefelhaltiger Triazinverbindungen |
| DE10017654A1 (de) * | 2000-04-08 | 2001-10-18 | Degussa | Organosiliciumverbindungen |
| JP6112755B2 (ja) * | 2011-04-26 | 2017-04-12 | 株式会社ブリヂストン | 防振ゴム組成物及び防振ゴム |
| JP5983049B2 (ja) * | 2011-06-01 | 2016-08-31 | 株式会社ブリヂストン | 防振ゴム組成物及び防振ゴム |
| JP5855931B2 (ja) * | 2011-12-26 | 2016-02-09 | 株式会社ブリヂストン | コンベアベルト用ゴム組成物及びコンベアベルト |
| 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 (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3923724A (en) * | 1951-01-28 | 1975-12-02 | Degussa | Processes for improving the processing characteristics of vulcanized elastomers |
| DE3014717A1 (de) * | 1980-04-17 | 1981-10-22 | Bayer Ag, 5090 Leverkusen | Vulkanisationssystem, dieses enthaltende kautschukmischung, sowie ein verfahren zur vulkanisation |
| JPS60230082A (ja) * | 1984-04-27 | 1985-11-15 | Optic Kk | 赤外線式検出装置の高周波雑音防止回路 |
| DE3438290A1 (de) * | 1984-10-19 | 1986-04-24 | Degussa Ag, 6000 Frankfurt | Bis-(2-ethylamino-4-diethylamino-s-triazin-6- yl)tetrasulfid,verfahren zur herstellung, verwendung und sie enthaltende vulkanisierbare mischungen |
| US4742118A (en) * | 1986-05-16 | 1988-05-03 | American Cyanamid Company | Urethane-functional s-triazine crosslinking agents and curable compositions containing the same |
-
1986
- 1986-04-01 DE DE3610794A patent/DE3610794C2/de not_active Expired - Lifetime
-
1987
- 1987-03-04 DE DE3789778T patent/DE3789778D1/de not_active Expired - Fee Related
- 1987-03-04 AT AT8787103018T patent/ATE105552T1/de not_active IP Right Cessation
- 1987-03-04 EP EP87103018A patent/EP0239816B1/de not_active Expired - Lifetime
- 1987-03-09 YU YU38187A patent/YU46045B/sh unknown
- 1987-03-11 ZA ZA871769A patent/ZA871769B/xx unknown
- 1987-03-11 IN IN199/CAL/87A patent/IN169093B/en unknown
- 1987-03-18 AU AU70156/87A patent/AU591249B2/en not_active Ceased
- 1987-03-23 NO NO871194A patent/NO871194L/no unknown
- 1987-03-30 BR BR8701445A patent/BR8701445A/pt not_active Application Discontinuation
- 1987-03-30 JP JP62074589A patent/JPS62240672A/ja active Pending
- 1987-03-30 DK DK160987A patent/DK160987A/da not_active IP Right Cessation
- 1987-03-31 CA CA000533428A patent/CA1325805C/en not_active Expired - Fee Related
- 1987-03-31 FI FI871409A patent/FI871409A7/fi not_active IP Right Cessation
- 1987-03-31 CS CS872247A patent/CS276589B6/cs unknown
- 1987-03-31 PL PL1987264909A patent/PL158593B1/pl unknown
- 1987-03-31 HU HU871389A patent/HU205918B/hu not_active IP Right Cessation
- 1987-03-31 DD DD87328211A patent/DD284007A5/de unknown
- 1987-03-31 CS CS904413A patent/CS277646B6/cs unknown
- 1987-03-31 DD DD30132387A patent/DD270302A5/de not_active IP Right Cessation
- 1987-04-01 PT PT84606A patent/PT84606B/pt not_active IP Right Cessation
- 1987-04-01 CN CN198787102447A patent/CN87102447A/zh active Pending
-
1988
- 1988-02-11 YU YU28188A patent/YU46252B/sh unknown
- 1988-02-11 YU YU28088A patent/YU46589B/sh unknown
-
1989
- 1989-12-12 IN IN1025/CAL/89A patent/IN169754B/en unknown
-
1990
- 1990-04-26 IN IN349/CAL/90A patent/IN170847B/en unknown
-
1992
- 1992-01-11 CN CN92100192A patent/CN1061982A/zh active Pending
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