CA1325805C - N,n'-substituted bis-(2,4-diamino-s-triazin-6-yl)- tetrasulfides and disproportionation products thereof, processes for their production and their use in vulcanizable rubber mixtures - Google Patents
N,n'-substituted bis-(2,4-diamino-s-triazin-6-yl)- tetrasulfides and disproportionation products thereof, processes for their production and their use in vulcanizable rubber mixturesInfo
- Publication number
- CA1325805C CA1325805C CA000533428A CA533428A CA1325805C CA 1325805 C CA1325805 C CA 1325805C CA 000533428 A CA000533428 A CA 000533428A CA 533428 A CA533428 A CA 533428A CA 1325805 C CA1325805 C CA 1325805C
- Authority
- CA
- Canada
- Prior art keywords
- triazin
- mixture
- tetrasulfide
- bis
- sulfur
- 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 - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 145
- 229920001971 elastomer Polymers 0.000 title claims abstract description 48
- 239000005060 rubber Substances 0.000 title claims abstract description 47
- 238000000034 method Methods 0.000 title claims abstract description 26
- 230000008569 process Effects 0.000 title claims abstract description 23
- 238000007323 disproportionation reaction Methods 0.000 title claims abstract description 15
- 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 title description 44
- 238000004519 manufacturing process Methods 0.000 title description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 90
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 69
- 239000011593 sulfur Substances 0.000 claims abstract description 67
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 64
- 238000004073 vulcanization Methods 0.000 claims abstract description 50
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- -1 2-hydroxypropyl Chemical group 0.000 claims abstract description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims abstract description 3
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 78
- 229920003052 natural elastomer Polymers 0.000 claims description 46
- 229920001194 natural rubber Polymers 0.000 claims description 46
- 239000000377 silicon dioxide Substances 0.000 claims description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 23
- 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 claims description 19
- 239000000243 solution Substances 0.000 claims description 15
- 239000006229 carbon black Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000000945 filler Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 229920003051 synthetic elastomer Polymers 0.000 claims description 5
- 239000005061 synthetic rubber Substances 0.000 claims description 5
- HAZJTCQWIDBCCE-UHFFFAOYSA-N 1h-triazine-6-thione Chemical compound SC1=CC=NN=N1 HAZJTCQWIDBCCE-UHFFFAOYSA-N 0.000 claims description 4
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- 239000012670 alkaline solution Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 3
- HPKCNTIOABWPNG-UHFFFAOYSA-N 2-n,2-n-dibutyl-6-[[4-(dibutylamino)-6-(ethylamino)-1,3,5-triazin-2-yl]tetrasulfanyl]-4-n-ethyl-1,3,5-triazine-2,4-diamine Chemical compound CCCCN(CCCC)C1=NC(NCC)=NC(SSSSC=2N=C(N=C(NCC)N=2)N(CCCC)CCCC)=N1 HPKCNTIOABWPNG-UHFFFAOYSA-N 0.000 claims description 2
- MMMXWPPZEQVKSR-UHFFFAOYSA-N 4-n-butyl-6-[[4-(butylamino)-6-(diethylamino)-1,3,5-triazin-2-yl]tetrasulfanyl]-2-n,2-n-diethyl-1,3,5-triazine-2,4-diamine Chemical compound CCN(CC)C1=NC(NCCCC)=NC(SSSSC=2N=C(N=C(NCCCC)N=2)N(CC)CC)=N1 MMMXWPPZEQVKSR-UHFFFAOYSA-N 0.000 claims description 2
- REJSNFBOVYVWOF-UHFFFAOYSA-N 4-n-butyl-6-[[4-(butylamino)-6-(dipropylamino)-1,3,5-triazin-2-yl]tetrasulfanyl]-2-n,2-n-dipropyl-1,3,5-triazine-2,4-diamine Chemical compound CCCN(CCC)C1=NC(NCCCC)=NC(SSSSC=2N=C(N=C(NCCCC)N=2)N(CCC)CCC)=N1 REJSNFBOVYVWOF-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 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 claims description 2
- XLOBVUROLSUMNV-UHFFFAOYSA-N 6-[[4-[di(propan-2-yl)amino]-6-(ethylamino)-1,3,5-triazin-2-yl]tetrasulfanyl]-4-n-ethyl-2-n,2-n-di(propan-2-yl)-1,3,5-triazine-2,4-diamine Chemical compound CC(C)N(C(C)C)C1=NC(NCC)=NC(SSSSC=2N=C(N=C(NCC)N=2)N(C(C)C)C(C)C)=N1 XLOBVUROLSUMNV-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 150000001924 cycloalkanes Chemical class 0.000 claims description 2
- 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 description 2
- JLQNHALFVCURHW-UHFFFAOYSA-N cyclooctasulfur Chemical compound S1SSSSSSS1 JLQNHALFVCURHW-UHFFFAOYSA-N 0.000 claims description 2
- 150000002170 ethers 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
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- 125000004434 sulfur atom Chemical group 0.000 claims 3
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- GPFQGFPYZKBHJP-UHFFFAOYSA-N 6-[[4-(diethylamino)-6-(propylamino)-1,3,5-triazin-2-yl]tetrasulfanyl]-2-n,2-n-diethyl-4-n-propyl-1,3,5-triazine-2,4-diamine Chemical compound CCN(CC)C1=NC(NCCC)=NC(SSSSC=2N=C(N=C(NCCC)N=2)N(CC)CC)=N1 GPFQGFPYZKBHJP-UHFFFAOYSA-N 0.000 claims 1
- KHXSVZBRKUVUGL-UHFFFAOYSA-N 6-[[4-[bis(2-methylpropyl)amino]-6-(ethylamino)-1,3,5-triazin-2-yl]tetrasulfanyl]-4-n-ethyl-2-n,2-n-bis(2-methylpropyl)-1,3,5-triazine-2,4-diamine Chemical compound CC(C)CN(CC(C)C)C1=NC(NCC)=NC(SSSSC=2N=C(N=C(NCC)N=2)N(CC(C)C)CC(C)C)=N1 KHXSVZBRKUVUGL-UHFFFAOYSA-N 0.000 claims 1
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- 239000012442 inert solvent Substances 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000003431 cross linking reagent Substances 0.000 abstract description 11
- XSASJDWHNUIMGC-UHFFFAOYSA-O N[S+](C1=NN=NC=C1)N Chemical class N[S+](C1=NN=NC=C1)N XSASJDWHNUIMGC-UHFFFAOYSA-O 0.000 abstract 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc oxide Inorganic materials [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 63
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- 239000011787 zinc oxide Substances 0.000 description 32
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 30
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 30
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- 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 27
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- MHKLKWCYGIBEQF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-ylsulfanyl)morpholine Chemical compound C1COCCN1SC1=NC2=CC=CC=C2S1 MHKLKWCYGIBEQF-UHFFFAOYSA-N 0.000 description 24
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- 238000010059 sulfur vulcanization Methods 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- 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
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- 229930003836 cresol Natural products 0.000 description 1
- WMWXXXSCZVGQAR-UHFFFAOYSA-N dialuminum;oxygen(2-);hydrate Chemical class O.[O-2].[O-2].[O-2].[Al+3].[Al+3] WMWXXXSCZVGQAR-UHFFFAOYSA-N 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
- 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
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
- 238000011049 filling Methods 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
- 229910052739 hydrogen 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
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000012764 mineral filler Substances 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
- 150000004005 nitrosamines Chemical class 0.000 description 1
- 239000012074 organic phase Substances 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
- 150000002978 peroxides Chemical class 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
- 230000003014 reinforcing effect Effects 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 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)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| 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 |
| DEP3610794.8 | 1986-04-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1325805C true CA1325805C (en) | 1994-01-04 |
Family
ID=6297621
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000533428A Expired - Fee Related CA1325805C (en) | 1986-04-01 | 1987-03-31 | N,n'-substituted bis-(2,4-diamino-s-triazin-6-yl)- tetrasulfides and disproportionation products thereof, processes for their production and their use in vulcanizable rubber mixtures |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0239816B1 (en]) |
| JP (1) | JPS62240672A (en]) |
| CN (2) | CN87102447A (en]) |
| AT (1) | ATE105552T1 (en]) |
| AU (1) | AU591249B2 (en]) |
| BR (1) | BR8701445A (en]) |
| CA (1) | CA1325805C (en]) |
| CS (2) | CS276589B6 (en]) |
| DD (2) | DD270302A5 (en]) |
| DE (2) | DE3610794C2 (en]) |
| DK (1) | DK160987A (en]) |
| FI (1) | FI871409A7 (en]) |
| HU (1) | HU205918B (en]) |
| IN (3) | IN169093B (en]) |
| NO (1) | NO871194L (en]) |
| PL (1) | PL158593B1 (en]) |
| PT (1) | PT84606B (en]) |
| YU (3) | YU46045B (en]) |
| ZA (1) | ZA871769B (en]) |
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 JP JP62074589A patent/JPS62240672A/ja active Pending
- 1987-03-30 BR BR8701445A patent/BR8701445A/pt not_active Application Discontinuation
- 1987-03-30 DK DK160987A patent/DK160987A/da not_active IP Right Cessation
- 1987-03-31 HU HU871389A patent/HU205918B/hu not_active IP Right Cessation
- 1987-03-31 DD DD30132387A patent/DD270302A5/de not_active IP Right Cessation
- 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 CS CS904413A patent/CS277646B6/cs unknown
- 1987-03-31 PL PL1987264909A patent/PL158593B1/pl unknown
- 1987-03-31 DD DD87328211A patent/DD284007A5/de unknown
- 1987-03-31 CA CA000533428A patent/CA1325805C/en not_active Expired - Fee Related
- 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 YU28088A patent/YU46589B/sh unknown
- 1988-02-11 YU YU28188A patent/YU46252B/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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |