DE1669954B2 - - Google Patents
Info
- Publication number
- DE1669954B2 DE1669954B2 DE1669954A DE1669954A DE1669954B2 DE 1669954 B2 DE1669954 B2 DE 1669954B2 DE 1669954 A DE1669954 A DE 1669954A DE 1669954 A DE1669954 A DE 1669954A DE 1669954 B2 DE1669954 B2 DE 1669954B2
- Authority
- DE
- Germany
- Prior art keywords
- rubber
- sulfur
- mixture
- weight
- triazine
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 claims description 36
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 30
- 229910052717 sulfur Inorganic materials 0.000 claims description 28
- 239000011593 sulfur Substances 0.000 claims description 28
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 26
- 238000004073 vulcanization Methods 0.000 claims description 15
- 239000006229 carbon black Substances 0.000 claims description 14
- 229920001971 elastomer Polymers 0.000 claims description 14
- 239000005060 rubber Substances 0.000 claims description 14
- 235000021355 Stearic acid Nutrition 0.000 claims description 13
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 13
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 13
- 239000008117 stearic acid Substances 0.000 claims description 13
- 239000011787 zinc oxide Substances 0.000 claims description 13
- 239000000945 filler Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 150000003918 triazines Chemical class 0.000 claims description 4
- 230000002787 reinforcement Effects 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 150000004760 silicates Chemical class 0.000 claims 1
- HAZJTCQWIDBCCE-UHFFFAOYSA-N 1h-triazine-6-thione Chemical class SC1=CC=NN=N1 HAZJTCQWIDBCCE-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 10
- 230000035882 stress Effects 0.000 description 10
- -1 sulfenyl chlorides Chemical class 0.000 description 9
- 244000043261 Hevea brasiliensis Species 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 229920003052 natural elastomer Polymers 0.000 description 8
- 229920001194 natural rubber Polymers 0.000 description 8
- 239000004071 soot Substances 0.000 description 8
- 238000005299 abrasion Methods 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000003993 interaction Effects 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 229920003048 styrene butadiene rubber Polymers 0.000 description 5
- HTWCYHMEBRGYFR-UHFFFAOYSA-N SC=1C=NN=NC1 Chemical class SC=1C=NN=NC1 HTWCYHMEBRGYFR-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 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
- 229920002857 polybutadiene Polymers 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- 239000005708 Sodium hypochlorite Substances 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 150000002019 disulfides Chemical class 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000006855 networking Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 2
- 229940054266 2-mercaptobenzothiazole Drugs 0.000 description 2
- DHGNMIYSSBLGHH-UHFFFAOYSA-N 5,6-diamino-1h-triazine-4-thione Chemical class NC=1NN=NC(=S)C=1N DHGNMIYSSBLGHH-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229920005549 butyl rubber Polymers 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000003247 decreasing effect Effects 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
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229920001195 polyisoprene Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 238000010626 work up procedure Methods 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 1
- DCNOKBWQRHOOBG-UHFFFAOYSA-N 2,6-bis(diethylamino)-1h-1,3,5-triazine-4-thione Chemical compound CCN(CC)C1=NC(=S)N=C(N(CC)CC)N1 DCNOKBWQRHOOBG-UHFFFAOYSA-N 0.000 description 1
- RTNUTCOTGVKVBR-UHFFFAOYSA-N 4-chlorotriazine Chemical class ClC1=CC=NN=N1 RTNUTCOTGVKVBR-UHFFFAOYSA-N 0.000 description 1
- JGPXJASXEZSOQV-UHFFFAOYSA-N C(C)N(N1NC(=CC(=N1)N(CC)CC)S)CC Chemical compound C(C)N(N1NC(=CC(=N1)N(CC)CC)S)CC JGPXJASXEZSOQV-UHFFFAOYSA-N 0.000 description 1
- UPTMLYVMUANIAW-UHFFFAOYSA-N C(C)NN1NC(=CC(=N1)NCC)S Chemical compound C(C)NN1NC(=CC(=N1)NCC)S UPTMLYVMUANIAW-UHFFFAOYSA-N 0.000 description 1
- PZFNRQMVPIJQPQ-UHFFFAOYSA-N C(C1=CC=CC=C1)SSC1=NN=NC=C1 Chemical compound C(C1=CC=CC=C1)SSC1=NN=NC=C1 PZFNRQMVPIJQPQ-UHFFFAOYSA-N 0.000 description 1
- PLJRNVGCJKUZDW-UHFFFAOYSA-N C(CCC)N(N1NC(=CC(=N1)N(CCCC)CCCC)S)CCCC Chemical compound C(CCC)N(N1NC(=CC(=N1)N(CCCC)CCCC)S)CCCC PLJRNVGCJKUZDW-UHFFFAOYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 229920000181 Ethylene propylene rubber Polymers 0.000 description 1
- 239000006237 Intermediate SAF Substances 0.000 description 1
- 229910019093 NaOCl Inorganic materials 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- PFJSYRJVLUFBRH-UHFFFAOYSA-N OS(OCC1=CC=CC=C1)(=S)=S Chemical compound OS(OCC1=CC=CC=C1)(=S)=S PFJSYRJVLUFBRH-UHFFFAOYSA-N 0.000 description 1
- 101001077374 Oryza sativa subsp. japonica UMP-CMP kinase 3 Proteins 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical class NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920003244 diene elastomer Polymers 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000013040 rubber vulcanization Methods 0.000 description 1
- VMCCEECNMRXCNF-UHFFFAOYSA-N s-hexylthiohydroxylamine Chemical compound CCCCCCSN VMCCEECNMRXCNF-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- HOZSKJBTDUAKBI-UHFFFAOYSA-M sodium butoxy-oxido-oxo-sulfanylidene-lambda6-sulfane Chemical compound S(=S)(=O)(OCCCC)[O-].[Na+] HOZSKJBTDUAKBI-UHFFFAOYSA-M 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 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 1
- 238000010059 sulfur vulcanization Methods 0.000 description 1
- 230000001550 time effect Effects 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
-
- 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19511669954 DE1669954A1 (de) | 1951-01-28 | 1951-01-28 | Verfahren zur Verbesserung der Gebrauchseigenschaften von Vulkanisaten |
| US470032A US3923724A (en) | 1951-01-28 | 1974-05-15 | Processes for improving the processing characteristics of vulcanized elastomers |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19511669954 DE1669954A1 (de) | 1951-01-28 | 1951-01-28 | Verfahren zur Verbesserung der Gebrauchseigenschaften von Vulkanisaten |
| DED0052613 | 1967-03-23 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1669954A1 DE1669954A1 (de) | 1970-08-20 |
| DE1669954B2 true DE1669954B2 (forum.php) | 1973-10-25 |
| DE1669954C3 DE1669954C3 (forum.php) | 1974-05-22 |
Family
ID=7054320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19511669954 Granted DE1669954A1 (de) | 1951-01-28 | 1951-01-28 | Verfahren zur Verbesserung der Gebrauchseigenschaften von Vulkanisaten |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3801537A (forum.php) |
| AT (1) | AT300353B (forum.php) |
| BE (1) | BE712531A (forum.php) |
| CA (1) | CA928709A (forum.php) |
| CH (1) | CH537423A (forum.php) |
| DE (1) | DE1669954A1 (forum.php) |
| DK (1) | DK118576B (forum.php) |
| ES (1) | ES351866A1 (forum.php) |
| FI (1) | FI47581C (forum.php) |
| FR (1) | FR1564112A (forum.php) |
| GB (1) | GB1201862A (forum.php) |
| IL (1) | IL29655A (forum.php) |
| LU (1) | LU55477A1 (forum.php) |
| NL (1) | NL6803363A (forum.php) |
| NO (1) | NO127352B (forum.php) |
| SE (1) | SE342636C (forum.php) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE791173A (fr) * | 1971-11-10 | 1973-05-09 | Degussa | Derives de s-triazines contenant des groupes naphtylamino et leur utilisation |
| US3938574A (en) * | 1973-10-11 | 1976-02-17 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler | Vulcanizable rubber mixture for tire treads having improved skid resistance |
| LU71476A1 (forum.php) * | 1974-04-22 | 1975-06-17 | ||
| US4000119A (en) * | 1974-06-24 | 1976-12-28 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler | Triazinesulfenimides of dicarboxylic acids |
| DE2430143C3 (de) * | 1974-06-24 | 1981-12-03 | Degussa Ag, 6000 Frankfurt | Triazinsulfenimide von Dicarbonsäuren, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE2819638C3 (de) | 1978-05-05 | 1986-11-13 | Degussa Ag, 6000 Frankfurt | Vulkanisierbare Halogenkautschuk-Mischungen |
| DE2933345C2 (de) | 1979-08-17 | 1983-01-20 | Degussa Ag, 6000 Frankfurt | Vulkanisierbare Kautschuk-Mischung auf Basis von halogenfreien Kautschuken und Verfahren zum Vulkanisieren dieser Kautschukmischungen |
| US4301260A (en) * | 1980-05-12 | 1981-11-17 | Monsanto Company | Vulcanizable rubber compositions scorch inhibited by 2-(thioamino)-4,6-diamino-1,3,5-triazines |
| JPS6147471A (ja) * | 1984-08-15 | 1986-03-07 | Shionogi & Co Ltd | トリアジン誘導体および除草剤 |
| 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 |
| US4673741A (en) * | 1984-10-19 | 1987-06-16 | Degussa Ag | Bis-(2-ethylamino-4-diethylamino-s-triazine-6-yl) tetrasulfide, process for its production, use and vulcanizable mixtures containing it |
| 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 |
| 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 |
| US4826925A (en) * | 1986-07-15 | 1989-05-02 | The Yokohama Rubber Co., Ltd. | Rubber compositions |
| US5206304A (en) * | 1988-06-22 | 1993-04-27 | Degussa Aktiengesellschaft | Vulcanizable rubber mixtures containing bis-(2,4-organylthio-triazine-6-yl) polysulfides |
| JP6462539B2 (ja) * | 2015-09-04 | 2019-01-30 | 四国化成工業株式会社 | トリアジン化合物、該化合物の合成方法およびその用途 |
| JP7377850B2 (ja) * | 2019-02-27 | 2023-11-10 | 住友化学株式会社 | 加硫ゴム組成物 |
| US12344725B2 (en) | 2020-04-22 | 2025-07-01 | Bridgestone Corporation | Rubber composition and rubber product |
-
1951
- 1951-01-28 DE DE19511669954 patent/DE1669954A1/de active Granted
-
1968
- 1968-02-14 LU LU55477D patent/LU55477A1/xx unknown
- 1968-02-28 CH CH293268A patent/CH537423A/de not_active IP Right Cessation
- 1968-03-08 NL NL6803363A patent/NL6803363A/xx unknown
- 1968-03-09 NO NO00918/68A patent/NO127352B/no unknown
- 1968-03-14 FI FI680697A patent/FI47581C/fi active
- 1968-03-19 IL IL29655A patent/IL29655A/xx unknown
- 1968-03-20 BE BE712531D patent/BE712531A/xx not_active IP Right Cessation
- 1968-03-22 CA CA015628A patent/CA928709A/en not_active Expired
- 1968-03-22 AT AT289268A patent/AT300353B/de not_active IP Right Cessation
- 1968-03-22 SE SE388668A patent/SE342636C/xx unknown
- 1968-03-22 FR FR145010A patent/FR1564112A/fr not_active Expired
- 1968-03-22 DK DK125868AA patent/DK118576B/da unknown
- 1968-03-22 ES ES351866A patent/ES351866A1/es not_active Expired
- 1968-03-22 GB GB03932/68A patent/GB1201862A/en not_active Expired
-
1973
- 1973-01-30 US US00328107A patent/US3801537A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| IL29655A (en) | 1973-02-28 |
| CA928709A (en) | 1973-06-19 |
| SE342636C (sv) | 1972-06-26 |
| FR1564112A (forum.php) | 1969-04-18 |
| GB1201862A (en) | 1970-08-12 |
| FI47581B (forum.php) | 1973-10-01 |
| AT300353B (de) | 1972-07-25 |
| DE1669954A1 (de) | 1970-08-20 |
| LU55477A1 (forum.php) | 1968-04-23 |
| DK118576B (da) | 1970-09-07 |
| NL6803363A (forum.php) | 1968-09-24 |
| FI47581C (fi) | 1974-01-10 |
| CH537423A (de) | 1973-05-31 |
| DE1669954C3 (forum.php) | 1974-05-22 |
| NO127352B (forum.php) | 1973-06-12 |
| ES351866A1 (es) | 1969-07-01 |
| US3801537A (en) | 1974-04-02 |
| BE712531A (forum.php) | 1968-07-31 |
| SE342636B (sv) | 1972-02-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |