DE2109244B2 - - Google Patents
Info
- Publication number
- DE2109244B2 DE2109244B2 DE2109244A DE2109244A DE2109244B2 DE 2109244 B2 DE2109244 B2 DE 2109244B2 DE 2109244 A DE2109244 A DE 2109244A DE 2109244 A DE2109244 A DE 2109244A DE 2109244 B2 DE2109244 B2 DE 2109244B2
- Authority
- DE
- Germany
- Prior art keywords
- disulfide
- accelerator
- triazin
- phr
- vulcanization
- 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 45
- 238000004073 vulcanization Methods 0.000 claims description 31
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 21
- 239000011593 sulfur Substances 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 21
- 229920001971 elastomer Polymers 0.000 claims description 13
- 239000005060 rubber Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 10
- 125000003363 1,3,5-triazinyl group Chemical class N1=C(N=CN=C1)* 0.000 claims 1
- -1 1,3,5-triazine disulfides Chemical class 0.000 description 35
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 35
- 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 32
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 30
- 238000010438 heat treatment Methods 0.000 description 16
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 14
- 229920003052 natural elastomer Polymers 0.000 description 12
- 229920001194 natural rubber Polymers 0.000 description 12
- 229960002447 thiram Drugs 0.000 description 12
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 10
- 244000043261 Hevea brasiliensis Species 0.000 description 8
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 8
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 239000006229 carbon black Substances 0.000 description 6
- 235000019241 carbon black Nutrition 0.000 description 6
- 229920003244 diene elastomer Polymers 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 150000003751 zinc Chemical class 0.000 description 5
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 150000001993 dienes Chemical class 0.000 description 4
- 229920003048 styrene butadiene rubber Polymers 0.000 description 4
- 229920003051 synthetic elastomer Polymers 0.000 description 4
- 239000005061 synthetic rubber Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 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 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 2
- 150000000182 1,3,5-triazines Chemical class 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-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
- 230000001133 acceleration Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 238000000137 annealing Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- DEQZTKGFXNUBJL-UHFFFAOYSA-N n-(1,3-benzothiazol-2-ylsulfanyl)cyclohexanamine Chemical compound C1CCCCC1NSC1=NC2=CC=CC=C2S1 DEQZTKGFXNUBJL-UHFFFAOYSA-N 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
- 239000008117 stearic acid Substances 0.000 description 2
- 238000010059 sulfur vulcanization Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- BUZICZZQJDLXJN-UHFFFAOYSA-N 3-azaniumyl-4-hydroxybutanoate Chemical compound OCC(N)CC(O)=O BUZICZZQJDLXJN-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
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- OWAMHAWEEZFJKY-UHFFFAOYSA-N C(C)NN1NC(=CC(=N1)N(CC)CC)SSC1=CC(=NN(N1)NCC)N(CC)CC Chemical compound C(C)NN1NC(=CC(=N1)N(CC)CC)SSC1=CC(=NN(N1)NCC)N(CC)CC OWAMHAWEEZFJKY-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241001441571 Hiodontidae Species 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 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
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-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
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000006232 furnace black Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920003246 polypentenamer Polymers 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004904 shortening 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
- C08K5/37—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)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2109244A DE2109244C3 (de) | 1971-02-26 | 1971-02-26 | Verfahren zur Vulkanisation von natürlichen und synthetischen Kautschuken |
| AU38352/72A AU458024B2 (en) | 1971-02-26 | 1972-01-26 | Process forthe vulcanization of natural or synthetic rubber |
| LU64677D LU64677A1 (Direct) | 1971-02-26 | 1972-01-28 | |
| US00228726A US3816323A (en) | 1971-02-26 | 1972-02-23 | Process for the vulcanization of natural or synthetic rubber |
| CA135,438A CA957797A (en) | 1971-02-26 | 1972-02-24 | Process for the vulcanization of natural or synthetic rubber |
| IT48526/72A IT948714B (it) | 1971-02-26 | 1972-02-24 | Procedimento ed accelerante per vulcanizzare gomme naturali e sintetiche |
| GB861372A GB1338195A (en) | 1971-02-26 | 1972-02-24 | Process for the vulcanisation of natural or synthetic rubber |
| ZA721251A ZA721251B (en) | 1971-02-26 | 1972-02-25 | Process for the vulcanization of natural or synthetic rubber |
| BE779887A BE779887A (fr) | 1971-02-26 | 1972-02-25 | Vulcanisation de caoutchoucs a l'aide d'une combinaison acceleratrice contenant notamment un disulfure de 1,3,5-triazine |
| NL7202518A NL7202518A (Direct) | 1971-02-26 | 1972-02-25 | |
| DD161126A DD96239A5 (Direct) | 1971-02-26 | 1972-02-25 | |
| ES400176A ES400176A1 (es) | 1971-02-26 | 1972-02-25 | Procedimiento para la vulcanizacion de caucho natural yno sintetico. |
| BR1062/72A BR7201062D0 (pt) | 1971-02-26 | 1972-02-25 | Processo para a vulcanizacao de borracha natural e ou sintetica |
| FR7206571A FR2127817A5 (Direct) | 1971-02-26 | 1972-02-25 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2109244A DE2109244C3 (de) | 1971-02-26 | 1971-02-26 | Verfahren zur Vulkanisation von natürlichen und synthetischen Kautschuken |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2109244A1 DE2109244A1 (de) | 1972-09-07 |
| DE2109244B2 true DE2109244B2 (Direct) | 1979-04-19 |
| DE2109244C3 DE2109244C3 (de) | 1980-01-03 |
Family
ID=5799954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2109244A Expired DE2109244C3 (de) | 1971-02-26 | 1971-02-26 | Verfahren zur Vulkanisation von natürlichen und synthetischen Kautschuken |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3816323A (Direct) |
| AU (1) | AU458024B2 (Direct) |
| BE (1) | BE779887A (Direct) |
| BR (1) | BR7201062D0 (Direct) |
| CA (1) | CA957797A (Direct) |
| DD (1) | DD96239A5 (Direct) |
| DE (1) | DE2109244C3 (Direct) |
| ES (1) | ES400176A1 (Direct) |
| FR (1) | FR2127817A5 (Direct) |
| GB (1) | GB1338195A (Direct) |
| IT (1) | IT948714B (Direct) |
| LU (1) | LU64677A1 (Direct) |
| NL (1) | NL7202518A (Direct) |
| ZA (1) | ZA721251B (Direct) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5423651A (en) * | 1977-07-22 | 1979-02-22 | Nippon Zeon Co Ltd | Readily processing polychloroprene rubber composition |
| DE2924660A1 (de) * | 1979-06-19 | 1981-01-15 | Bayer Ag | Verfahren zur herstellung von lagerstabilen 2-chlor-1,3-butadien/schwefel - copolymerisaten |
-
1971
- 1971-02-26 DE DE2109244A patent/DE2109244C3/de not_active Expired
-
1972
- 1972-01-26 AU AU38352/72A patent/AU458024B2/en not_active Expired
- 1972-01-28 LU LU64677D patent/LU64677A1/xx unknown
- 1972-02-23 US US00228726A patent/US3816323A/en not_active Expired - Lifetime
- 1972-02-24 GB GB861372A patent/GB1338195A/en not_active Expired
- 1972-02-24 IT IT48526/72A patent/IT948714B/it active
- 1972-02-24 CA CA135,438A patent/CA957797A/en not_active Expired
- 1972-02-25 BE BE779887A patent/BE779887A/xx unknown
- 1972-02-25 ZA ZA721251A patent/ZA721251B/xx unknown
- 1972-02-25 NL NL7202518A patent/NL7202518A/xx not_active Application Discontinuation
- 1972-02-25 DD DD161126A patent/DD96239A5/xx unknown
- 1972-02-25 FR FR7206571A patent/FR2127817A5/fr not_active Expired
- 1972-02-25 ES ES400176A patent/ES400176A1/es not_active Expired
- 1972-02-25 BR BR1062/72A patent/BR7201062D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3816323A (en) | 1974-06-11 |
| NL7202518A (Direct) | 1972-08-29 |
| DD96239A5 (Direct) | 1973-03-12 |
| AU3835272A (en) | 1973-08-02 |
| DE2109244A1 (de) | 1972-09-07 |
| BE779887A (fr) | 1972-08-25 |
| BR7201062D0 (pt) | 1973-05-24 |
| CA957797A (en) | 1974-11-12 |
| AU458024B2 (en) | 1975-01-14 |
| IT948714B (it) | 1973-06-11 |
| GB1338195A (en) | 1973-11-21 |
| ES400176A1 (es) | 1974-12-16 |
| ZA721251B (en) | 1972-11-29 |
| DE2109244C3 (de) | 1980-01-03 |
| LU64677A1 (Direct) | 1972-06-26 |
| FR2127817A5 (Direct) | 1972-10-13 |
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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 |