DE2120288C3 - Verfahren zum Vulkanisieren von natürlichen und synthetischen Kautschuken aus halogenfreien Dienen - Google Patents
Verfahren zum Vulkanisieren von natürlichen und synthetischen Kautschuken aus halogenfreien DienenInfo
- Publication number
- DE2120288C3 DE2120288C3 DE2120288A DE2120288A DE2120288C3 DE 2120288 C3 DE2120288 C3 DE 2120288C3 DE 2120288 A DE2120288 A DE 2120288A DE 2120288 A DE2120288 A DE 2120288A DE 2120288 C3 DE2120288 C3 DE 2120288C3
- Authority
- DE
- Germany
- Prior art keywords
- triazine
- accelerator
- bis
- mixture
- sulfenamido
- 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
Links
- 238000000034 method Methods 0.000 title claims description 11
- 229920003052 natural elastomer Polymers 0.000 title claims description 11
- 229920001194 natural rubber Polymers 0.000 title claims description 11
- 229920003051 synthetic elastomer Polymers 0.000 title claims description 6
- 239000005061 synthetic rubber Substances 0.000 title claims description 6
- 150000001993 dienes Chemical class 0.000 title description 5
- 239000000203 mixture Substances 0.000 claims description 57
- 238000004073 vulcanization Methods 0.000 claims description 35
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 239000011593 sulfur Substances 0.000 claims description 17
- -1 1,3,5-triazine compound Chemical class 0.000 claims description 13
- 229920001971 elastomer Polymers 0.000 claims description 9
- 239000005060 rubber Substances 0.000 claims description 9
- 150000000182 1,3,5-triazines Chemical class 0.000 claims description 3
- 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 29
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 24
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 17
- 238000010438 heat treatment Methods 0.000 description 13
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 13
- 229960002447 thiram Drugs 0.000 description 13
- 229920003244 diene elastomer Polymers 0.000 description 8
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 0.000 description 8
- BUZICZZQJDLXJN-UHFFFAOYSA-N 3-azaniumyl-4-hydroxybutanoate Chemical compound OCC(N)CC(O)=O BUZICZZQJDLXJN-UHFFFAOYSA-N 0.000 description 7
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229920003048 styrene butadiene rubber Polymers 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 244000043261 Hevea brasiliensis Species 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 150000003751 zinc Chemical class 0.000 description 4
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 235000019241 carbon black Nutrition 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 3
- 238000010059 sulfur vulcanization Methods 0.000 description 3
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 2
- BBHYMRLYCSRVOS-UHFFFAOYSA-N 4-n,6-n-bis(cyclohexylsulfanyl)-2-n,2-n-diethyl-1,3,5-triazine-2,4,6-triamine Chemical compound N=1C(NSC2CCCCC2)=NC(N(CC)CC)=NC=1NSC1CCCCC1 BBHYMRLYCSRVOS-UHFFFAOYSA-N 0.000 description 2
- 229920000459 Nitrile rubber Polymers 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- CGTGVSBVWWZIDT-UHFFFAOYSA-N isoquinolin-6-yl(trimethyl)stannane Chemical compound C1=NC=CC2=CC([Sn](C)(C)C)=CC=C21 CGTGVSBVWWZIDT-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical class C1NNNC=C1 FIDRAVVQGKNYQK-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
- HLBZWYXLQJQBKU-UHFFFAOYSA-N 4-(morpholin-4-yldisulfanyl)morpholine Chemical compound C1COCCN1SSN1CCOCC1 HLBZWYXLQJQBKU-UHFFFAOYSA-N 0.000 description 1
- TXLINXBIWJYFNR-UHFFFAOYSA-N 4-phenylpyridine-2-carbonitrile Chemical compound C1=NC(C#N)=CC(C=2C=CC=CC=2)=C1 TXLINXBIWJYFNR-UHFFFAOYSA-N 0.000 description 1
- 239000006237 Intermediate SAF Substances 0.000 description 1
- 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 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000003712 anti-aging 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
- 235000015111 chews Nutrition 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 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
- 238000005554 pickling Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920003246 polypentenamer Polymers 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000010057 rubber processing Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000011787 zinc oxide Substances 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- 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
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)
- Heating, Cooling, Or Curing Plastics Or The Like In General (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2120288A DE2120288C3 (de) | 1971-04-26 | 1971-04-26 | Verfahren zum Vulkanisieren von natürlichen und synthetischen Kautschuken aus halogenfreien Dienen |
| LU65081D LU65081A1 (enExample) | 1971-04-26 | 1972-03-30 | |
| AU41408/72A AU470965B2 (en) | 1971-04-26 | 1972-04-20 | Process forthe vulcanisation of natural and/or synthetic rubbers made from halogen-free dienes |
| CA140,375A CA975485A (en) | 1971-04-26 | 1972-04-24 | Process for the vulcanisation of natural and/or synthetic rubbers made from halogen-free dienes |
| BE782565A BE782565A (fr) | 1971-04-26 | 1972-04-24 | Procede perfectionne pour vulcaniser les caoutchoucs de dienes exempts d'halogene |
| GB1888372A GB1361117A (en) | 1971-04-26 | 1972-04-24 | Vulcanisation of natural and/or synthetic rubbers made from halo gen-free dienes |
| IT49806/72A IT960788B (it) | 1971-04-26 | 1972-04-24 | Procedimento ed acceleratore per vulcanizzare comme dieniche |
| US00246646A US3844970A (en) | 1971-04-26 | 1972-04-24 | Process for the vulcanisation of natural and/or synthetic rubbers made from halogen-free dienes |
| BR2504/72A BR7202504D0 (pt) | 1971-04-26 | 1972-04-25 | Processo para vulcanizacao de borrachas naturais e sinteticas constituidas de dienos isentos de halogeneo bem como acelerador de vulcanizacao e composicao de vulcanizacao empregados no mesmo |
| ZA722801A ZA722801B (en) | 1971-04-26 | 1972-04-25 | Process for the vulcanisation of natural and/or synthetic rubbers made from halogen free dienes |
| ES402084A ES402084A1 (es) | 1971-04-26 | 1972-04-25 | Procedimiento para la vulcanizacion de caucho natural y sintetico preparado a partir de dienos libres de halogeno. |
| DD162568A DD96486A5 (enExample) | 1971-04-26 | 1972-04-25 | |
| NL7205588A NL7205588A (enExample) | 1971-04-26 | 1972-04-25 | |
| FR727214914A FR2134563B1 (enExample) | 1971-04-26 | 1972-04-26 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2120288A DE2120288C3 (de) | 1971-04-26 | 1971-04-26 | Verfahren zum Vulkanisieren von natürlichen und synthetischen Kautschuken aus halogenfreien Dienen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2120288A1 DE2120288A1 (de) | 1972-11-16 |
| DE2120288B2 DE2120288B2 (de) | 1979-06-21 |
| DE2120288C3 true DE2120288C3 (de) | 1980-02-14 |
Family
ID=5805924
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2120288A Expired DE2120288C3 (de) | 1971-04-26 | 1971-04-26 | Verfahren zum Vulkanisieren von natürlichen und synthetischen Kautschuken aus halogenfreien Dienen |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3844970A (enExample) |
| AU (1) | AU470965B2 (enExample) |
| BE (1) | BE782565A (enExample) |
| BR (1) | BR7202504D0 (enExample) |
| CA (1) | CA975485A (enExample) |
| DD (1) | DD96486A5 (enExample) |
| DE (1) | DE2120288C3 (enExample) |
| ES (1) | ES402084A1 (enExample) |
| FR (1) | FR2134563B1 (enExample) |
| GB (1) | GB1361117A (enExample) |
| IT (1) | IT960788B (enExample) |
| LU (1) | LU65081A1 (enExample) |
| NL (1) | NL7205588A (enExample) |
| ZA (1) | ZA722801B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4209596A (en) * | 1973-04-28 | 1980-06-24 | Mitsuboshi Belting, Ltd. | Two step process for producing vulcanized rubber |
| US4244843A (en) * | 1973-04-28 | 1981-01-13 | Mitsubishi Belting, Ltd. | Covulcanized rubber |
| US4012332A (en) * | 1974-01-30 | 1977-03-15 | American Cyanamid Company | Rubber vulcanization accelerator composition |
| DE3014717A1 (de) * | 1980-04-17 | 1981-10-22 | Bayer Ag, 5090 Leverkusen | Vulkanisationssystem, dieses enthaltende kautschukmischung, sowie ein verfahren zur vulkanisation |
| US4339577A (en) * | 1980-05-12 | 1982-07-13 | Monsanto Company | 2-(Thioamino)-4,6-diamino-1,3,5-triazines |
| DE102007057133A1 (de) * | 2007-11-28 | 2009-06-04 | Robert Bosch Gmbh | Wischgummi für Scheibenwischer |
| CN116041808B (zh) * | 2022-12-13 | 2025-08-01 | 广东金发科技有限公司 | 一种丁腈胶乳组合物、丁腈手套及制备方法和应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3240749A (en) * | 1961-04-11 | 1966-03-15 | Geigy Chem Corp | Method of stabilization of rubber with a substituted triazine and compositions stabilized thereby |
| CH473605A (de) * | 1965-04-20 | 1969-06-15 | Ciba Geigy | Verwendung von neuen Aryl-1,3,5-triazin-Derivaten als Stabilisierungsmittel für nicht-textile organische Materialien |
| US3250772A (en) * | 1965-07-20 | 1966-05-10 | Geigy Chem Corp | Sulfur-substituted 1, 3, 5-triazines |
| DE1620178A1 (de) * | 1965-12-03 | 1970-03-12 | Ruhrchemie Ag | Verfahren zur Herstellung von Aminoalkylamino-s-triazinen |
| US3558739A (en) * | 1968-08-29 | 1971-01-26 | Goodyear Tire & Rubber | Accelerator systems comprising 2-(aminopolythio)-thiazole and thiurams |
-
1971
- 1971-04-26 DE DE2120288A patent/DE2120288C3/de not_active Expired
-
1972
- 1972-03-30 LU LU65081D patent/LU65081A1/xx unknown
- 1972-04-20 AU AU41408/72A patent/AU470965B2/en not_active Expired
- 1972-04-24 CA CA140,375A patent/CA975485A/en not_active Expired
- 1972-04-24 US US00246646A patent/US3844970A/en not_active Expired - Lifetime
- 1972-04-24 IT IT49806/72A patent/IT960788B/it active
- 1972-04-24 GB GB1888372A patent/GB1361117A/en not_active Expired
- 1972-04-24 BE BE782565A patent/BE782565A/xx unknown
- 1972-04-25 ES ES402084A patent/ES402084A1/es not_active Expired
- 1972-04-25 DD DD162568A patent/DD96486A5/xx unknown
- 1972-04-25 BR BR2504/72A patent/BR7202504D0/pt unknown
- 1972-04-25 ZA ZA722801A patent/ZA722801B/xx unknown
- 1972-04-25 NL NL7205588A patent/NL7205588A/xx not_active Application Discontinuation
- 1972-04-26 FR FR727214914A patent/FR2134563B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7205588A (enExample) | 1972-10-30 |
| BR7202504D0 (pt) | 1973-05-24 |
| CA975485A (en) | 1975-09-30 |
| DD96486A5 (enExample) | 1973-03-20 |
| ZA722801B (en) | 1973-02-28 |
| DE2120288B2 (de) | 1979-06-21 |
| LU65081A1 (enExample) | 1972-07-11 |
| IT960788B (it) | 1973-11-30 |
| FR2134563B1 (enExample) | 1973-07-13 |
| AU470965B2 (en) | 1976-04-08 |
| FR2134563A1 (enExample) | 1972-12-08 |
| GB1361117A (en) | 1974-07-24 |
| BE782565A (fr) | 1972-10-24 |
| US3844970A (en) | 1974-10-29 |
| DE2120288A1 (de) | 1972-11-16 |
| ES402084A1 (es) | 1975-03-01 |
| AU4140872A (en) | 1973-10-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| EGA | New person/name/address of the applicant | ||
| 8339 | Ceased/non-payment of the annual fee |