SU1209036A3 - Способ ингибировани подвулканизации резиновой смеси - Google Patents
Способ ингибировани подвулканизации резиновой смеси Download PDFInfo
- Publication number
- SU1209036A3 SU1209036A3 SU823503160A SU3503160A SU1209036A3 SU 1209036 A3 SU1209036 A3 SU 1209036A3 SU 823503160 A SU823503160 A SU 823503160A SU 3503160 A SU3503160 A SU 3503160A SU 1209036 A3 SU1209036 A3 SU 1209036A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- triazine
- phenylthio
- diamine
- triamine
- tetra
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 14
- 229920001971 elastomer Polymers 0.000 title claims abstract description 9
- 239000005060 rubber Substances 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims description 7
- 238000004073 vulcanization Methods 0.000 title claims description 7
- 230000002401 inhibitory effect Effects 0.000 title claims description 3
- 230000002028 premature Effects 0.000 title 1
- -1 cyano, acetoxy Chemical group 0.000 claims abstract description 16
- 239000003112 inhibitor Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 33
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 6
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- HOXINJBQVZWYGZ-UHFFFAOYSA-N fenbutatin oxide Chemical compound C=1C=CC=CC=1C(C)(C)C[Sn](O[Sn](CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C1=CC=CC=C1 HOXINJBQVZWYGZ-UHFFFAOYSA-N 0.000 claims description 4
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011787 zinc oxide Substances 0.000 claims description 3
- LEZSQBGBCPCMMC-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(phenylsulfanyl)-1,3,5-triazine-2,4,6-triamine Chemical compound C=1C=CC=CC=1SN(C=1N=C(N=C(N=1)N(SC=1C=CC=CC=1)SC=1C=CC=CC=1)N(SC=1C=CC=CC=1)SC=1C=CC=CC=1)SC1=CC=CC=C1 LEZSQBGBCPCMMC-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- ZVKIBXXMFHRQJV-UHFFFAOYSA-N 6-phenylsulfanyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(SC=2C=CC=CC=2)=N1 ZVKIBXXMFHRQJV-UHFFFAOYSA-N 0.000 claims description 2
- 235000021355 Stearic acid Nutrition 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 2
- 239000004071 soot Substances 0.000 claims description 2
- 239000008117 stearic acid Substances 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229920003052 natural elastomer Polymers 0.000 claims 2
- 229920001194 natural rubber Polymers 0.000 claims 2
- 150000003918 triazines Chemical class 0.000 claims 2
- 241001209177 Akis Species 0.000 claims 1
- FYCMXSUPJZCEFR-UHFFFAOYSA-N C1=CC=C(C=C1)SNC2=NC(=NC(=N2)N)N Chemical compound C1=CC=C(C=C1)SNC2=NC(=NC(=N2)N)N FYCMXSUPJZCEFR-UHFFFAOYSA-N 0.000 claims 1
- GFQRVGKVOSEDJX-UHFFFAOYSA-N CCCCCCCCCCCCCCCCCC(O)=O.[O-2].O.S.[Zn+2] Chemical compound CCCCCCCCCCCCCCCCCC(O)=O.[O-2].O.S.[Zn+2] GFQRVGKVOSEDJX-UHFFFAOYSA-N 0.000 claims 1
- 239000006229 carbon black Substances 0.000 claims 1
- 239000003921 oil Substances 0.000 claims 1
- 238000010059 sulfur vulcanization Methods 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 8
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- AGJAUFUNZWHLKE-UHFFFAOYSA-N (2E,4E)-N-isobutyl-2,4-tetradecadienamide Natural products CCCCCCCCCC=CC=CC(=O)NCC(C)C AGJAUFUNZWHLKE-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KXUNSBPEPPPPPS-UHFFFAOYSA-N C1=CC=C(C=C1)C2=NC(=NC(=N2)NSC3=CC=CC=C3)N Chemical compound C1=CC=C(C=C1)C2=NC(=NC(=N2)NSC3=CC=CC=C3)N KXUNSBPEPPPPPS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- 239000002174 Styrene-butadiene Substances 0.000 description 2
- DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 2
- 229940086542 triethylamine Drugs 0.000 description 2
- VZXTWGWHSMCWGA-MQIHXRCWSA-N 1,3,5-triazine-2,4-diamine Chemical class [15NH2]C1=NC=NC([15NH2])=N1 VZXTWGWHSMCWGA-MQIHXRCWSA-N 0.000 description 1
- UXECJAJBAWUAMQ-UHFFFAOYSA-N 1h-triazine-2,4,6-triamine Chemical compound NN1NC(N)=CC(N)=N1 UXECJAJBAWUAMQ-UHFFFAOYSA-N 0.000 description 1
- FVFVNNKYKYZTJU-UHFFFAOYSA-N 6-chloro-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(Cl)=N1 FVFVNNKYKYZTJU-UHFFFAOYSA-N 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- CEHUTIDTUROJFO-UHFFFAOYSA-N C1=CC=C(C=C1)SNC2=NC(=NC(=N2)N)Cl Chemical compound C1=CC=C(C=C1)SNC2=NC(=NC(=N2)N)Cl CEHUTIDTUROJFO-UHFFFAOYSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 241001441571 Hiodontidae Species 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- 235000002905 Rumex vesicarius Nutrition 0.000 description 1
- 244000207667 Rumex vesicarius Species 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
- 239000002253 acid Substances 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 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
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- JWUKZUIGOJBEPC-UHFFFAOYSA-N phenyl thiohypochlorite Chemical compound ClSC1=CC=CC=C1 JWUKZUIGOJBEPC-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- MAUIZVRLYLDWDK-UHFFFAOYSA-N propan-2-yl thiohypochlorite Chemical compound CC(C)SCl MAUIZVRLYLDWDK-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/43—Compounds containing sulfur bound to nitrogen
- C08K5/44—Sulfenamides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
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)
- Plural Heterocyclic Compounds (AREA)
- Heating, Cooling, Or Curing Plastics Or The Like In General (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/312,572 US4380609A (en) | 1981-10-19 | 1981-10-19 | Prevulcanization inhibitors of thio-triazine-amines for rubber |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1209036A3 true SU1209036A3 (ru) | 1986-01-30 |
Family
ID=23212084
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU823503160A SU1209036A3 (ru) | 1981-10-19 | 1982-10-18 | Способ ингибировани подвулканизации резиновой смеси |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4380609A (enExample) |
| EP (1) | EP0078784B1 (enExample) |
| JP (1) | JPS5879039A (enExample) |
| KR (1) | KR850001886B1 (enExample) |
| AU (1) | AU548971B2 (enExample) |
| BR (1) | BR8206057A (enExample) |
| CA (1) | CA1184914A (enExample) |
| CS (1) | CS236687B2 (enExample) |
| DD (1) | DD203726A5 (enExample) |
| DE (1) | DE3264578D1 (enExample) |
| ES (1) | ES8404389A1 (enExample) |
| SU (1) | SU1209036A3 (enExample) |
| UA (1) | UA5962A1 (enExample) |
| ZA (1) | ZA827616B (enExample) |
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 |
| 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 |
| US6235819B1 (en) * | 1997-12-31 | 2001-05-22 | Bridgestone Corporation | Process to scavenge amines in polymeric compounds by treatment with triazine derivatives and compositions therefrom |
| US6063873A (en) * | 1997-12-31 | 2000-05-16 | Bridgestone Corporation | Process to scavenge amines in polymeric compounds by treatment with triazine derivatives, and compositions therefrom |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3382219A (en) * | 1966-01-10 | 1968-05-07 | Monsanto Co | Inhibiting pre-vulcanization of rubber with thioamines of phenylenediamine or dihydroquinoline |
| US3473667A (en) * | 1968-01-08 | 1969-10-21 | Monsanto Co | Certain n-thio-2-imidazolidinones |
| US3640976A (en) * | 1970-03-09 | 1972-02-08 | Monsanto Co | Certain cycloalkylsulfenamides as prevulcanization inhibitors |
| US3817742A (en) * | 1971-05-12 | 1974-06-18 | Chevron Res | Substituted triazines |
| 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 |
| US4339577A (en) * | 1980-05-12 | 1982-07-13 | Monsanto Company | 2-(Thioamino)-4,6-diamino-1,3,5-triazines |
-
1981
- 1981-10-19 US US06/312,572 patent/US4380609A/en not_active Expired - Lifetime
-
1982
- 1982-10-15 DE DE8282870053T patent/DE3264578D1/de not_active Expired
- 1982-10-15 ES ES516572A patent/ES8404389A1/es not_active Expired
- 1982-10-15 EP EP82870053A patent/EP0078784B1/en not_active Expired
- 1982-10-18 JP JP57181502A patent/JPS5879039A/ja active Granted
- 1982-10-18 AU AU89450/82A patent/AU548971B2/en not_active Ceased
- 1982-10-18 BR BR8206057A patent/BR8206057A/pt not_active IP Right Cessation
- 1982-10-18 KR KR8204692A patent/KR850001886B1/ko not_active Expired
- 1982-10-18 ZA ZA827616A patent/ZA827616B/xx unknown
- 1982-10-18 CS CS827388A patent/CS236687B2/cs unknown
- 1982-10-18 SU SU823503160A patent/SU1209036A3/ru active
- 1982-10-18 CA CA000413609A patent/CA1184914A/en not_active Expired
- 1982-10-18 UA UA3503160A patent/UA5962A1/uk unknown
- 1982-10-18 DD DD82244079A patent/DD203726A5/de not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| Авторское свидетельство СССР № 767144, кл. С 08 L 11/00, 1978. * |
Also Published As
| Publication number | Publication date |
|---|---|
| CS236687B2 (en) | 1985-05-15 |
| EP0078784A1 (en) | 1983-05-11 |
| AU8945082A (en) | 1983-04-28 |
| EP0078784B1 (en) | 1985-07-03 |
| JPH0242105B2 (enExample) | 1990-09-20 |
| KR840002014A (ko) | 1984-06-11 |
| JPS5879039A (ja) | 1983-05-12 |
| US4380609A (en) | 1983-04-19 |
| AU548971B2 (en) | 1986-01-09 |
| DE3264578D1 (en) | 1985-08-08 |
| KR850001886B1 (ko) | 1985-12-28 |
| UA5962A1 (uk) | 1994-12-29 |
| ES516572A0 (es) | 1984-04-16 |
| CA1184914A (en) | 1985-04-02 |
| ES8404389A1 (es) | 1984-04-16 |
| BR8206057A (pt) | 1983-09-13 |
| DD203726A5 (de) | 1983-11-02 |
| ZA827616B (en) | 1983-08-31 |
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