DE2008479A1 - Verfahren zum Vulkanisieren von Homobzw. Copoiymerisaten konjugierter Diene - Google Patents
Verfahren zum Vulkanisieren von Homobzw. Copoiymerisaten konjugierter DieneInfo
- Publication number
- DE2008479A1 DE2008479A1 DE19702008479 DE2008479A DE2008479A1 DE 2008479 A1 DE2008479 A1 DE 2008479A1 DE 19702008479 DE19702008479 DE 19702008479 DE 2008479 A DE2008479 A DE 2008479A DE 2008479 A1 DE2008479 A1 DE 2008479A1
- Authority
- DE
- Germany
- Prior art keywords
- weight
- parts
- dithiol
- vulcanization
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 13
- 150000001993 dienes Chemical class 0.000 title description 5
- 238000007334 copolymerization reaction Methods 0.000 title 1
- 238000004073 vulcanization Methods 0.000 claims description 51
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 239000011593 sulfur Substances 0.000 claims description 24
- 150000004662 dithiols Chemical class 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 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 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 2
- 230000001588 bifunctional effect Effects 0.000 claims description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 2
- NVUDVUDVVXAWGV-UHFFFAOYSA-N dodecane-1,12-dithiol Chemical compound SCCCCCCCCCCCCS NVUDVUDVVXAWGV-UHFFFAOYSA-N 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 41
- 229920002857 polybutadiene Polymers 0.000 description 13
- 239000005062 Polybutadiene Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 11
- 230000032683 aging Effects 0.000 description 10
- 229920001971 elastomer Polymers 0.000 description 10
- 239000005060 rubber Substances 0.000 description 10
- FKDXNKLATUKJAL-UHFFFAOYSA-N dodecane-1,1-dithiol Chemical compound CCCCCCCCCCCC(S)S FKDXNKLATUKJAL-UHFFFAOYSA-N 0.000 description 9
- WGARMULIELDQEH-UHFFFAOYSA-N n-cyclohexyl-1,3-benzothiazole-2-sulfinamide Chemical compound N=1C2=CC=CC=C2SC=1S(=O)NC1CCCCC1 WGARMULIELDQEH-UHFFFAOYSA-N 0.000 description 9
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- 229920001195 polyisoprene Polymers 0.000 description 8
- DMYOHQBLOZMDLP-UHFFFAOYSA-N 1-[2-(2-hydroxy-3-piperidin-1-ylpropoxy)phenyl]-3-phenylpropan-1-one Chemical compound C1CCCCN1CC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 DMYOHQBLOZMDLP-UHFFFAOYSA-N 0.000 description 6
- 229920001079 Thiokol (polymer) Polymers 0.000 description 6
- 230000003679 aging effect Effects 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 239000003921 oil Substances 0.000 description 5
- 235000021355 Stearic acid Nutrition 0.000 description 4
- 239000006229 carbon black Substances 0.000 description 4
- 235000019241 carbon black Nutrition 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
- 239000008117 stearic acid Substances 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004071 soot Substances 0.000 description 2
- 230000035882 stress Effects 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- -1 vinyl aromatic compounds Chemical class 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
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229920008128 Ameripol Polymers 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- LULCPJWUGUVEFU-UHFFFAOYSA-N Phthiocol Natural products C1=CC=C2C(=O)C(C)=C(O)C(=O)C2=C1 LULCPJWUGUVEFU-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- CSNJTIWCTNEOSW-UHFFFAOYSA-N carbamothioylsulfanyl carbamodithioate Chemical compound NC(=S)SSC(N)=S CSNJTIWCTNEOSW-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 150000001869 cobalt compounds Chemical class 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 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
- 150000003557 thiazoles Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004636 vulcanized rubber 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
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)
- Processes Of Treating Macromolecular Substances (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702008479 DE2008479A1 (de) | 1970-02-24 | 1970-02-24 | Verfahren zum Vulkanisieren von Homobzw. Copoiymerisaten konjugierter Diene |
| JP45117870A JPS4921290B1 (enExample) | 1970-02-24 | 1970-12-25 | |
| FR7105137A FR2078633A5 (enExample) | 1970-02-24 | 1971-02-16 | |
| US00117757A US3781250A (en) | 1970-02-24 | 1971-02-22 | Process for the vulcanization of homo-or copolymers of conjugated dienes |
| GB2235471A GB1330058A (en) | 1970-02-24 | 1971-04-19 | Process for the vulcanisation of homopolymers or copolymers of conjugated dienes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702008479 DE2008479A1 (de) | 1970-02-24 | 1970-02-24 | Verfahren zum Vulkanisieren von Homobzw. Copoiymerisaten konjugierter Diene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2008479A1 true DE2008479A1 (de) | 1971-09-09 |
Family
ID=5763185
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702008479 Pending DE2008479A1 (de) | 1970-02-24 | 1970-02-24 | Verfahren zum Vulkanisieren von Homobzw. Copoiymerisaten konjugierter Diene |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3781250A (enExample) |
| JP (1) | JPS4921290B1 (enExample) |
| DE (1) | DE2008479A1 (enExample) |
| FR (1) | FR2078633A5 (enExample) |
| GB (1) | GB1330058A (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51138489A (en) * | 1975-05-27 | 1976-11-30 | Tokico Ltd | Heat quantity calculator |
| JP2001139728A (ja) * | 1999-11-17 | 2001-05-22 | Bridgestone Corp | ゴム組成物 |
| US20030127169A1 (en) * | 2001-10-30 | 2003-07-10 | Bridgestone/Firestone, Inc. | Elastomers with long chain crosslinks to increase abrasion resistance |
| DE102004022106A1 (de) * | 2004-05-05 | 2005-11-24 | Bayer Ag | Verwendung von Metall-Alkandithiole als Vernetzungsagenzien für ungesättigte Kautschuke |
| BRPI0719461A2 (pt) * | 2006-12-19 | 2014-02-04 | Dow Global Technologies Inc | "composição, composição reticulada, banda de rodagem de pneu, polimero modificado, método para preparar uma composição de polimero elastomérico vulcanizado, modificador, método para preparar a composição de polimero modificado e artigo" |
| FR2929616B1 (fr) * | 2008-04-08 | 2011-09-09 | Total France | Procede de reticulation de compositions bitume/polymere presentant des emissions reduites d'hydrogene sulfure |
| CN102395473B (zh) * | 2009-04-29 | 2014-12-17 | 米其林集团总公司 | 用于重型车辆轮胎的胎面 |
| CN102656023B (zh) * | 2009-12-16 | 2015-01-21 | 米其林集团总公司 | 用于重型车辆轮胎的高二氧化硅含量 |
| JP5809020B2 (ja) * | 2011-10-21 | 2015-11-10 | 株式会社ブリヂストン | ゴム組成物及びゴム組成物の製造方法 |
| FR2984329B1 (fr) * | 2011-12-20 | 2014-11-21 | Total Raffinage Marketing | Polymere greffe et composition bitume/polymere a reticulation thermoreversible contenant un tel polymere |
| US9085676B2 (en) | 2012-06-28 | 2015-07-21 | The Goodyear Tire & Rubber Company | Rubber composition having a crosslink distribution, its preparation and article with component |
| KR101671560B1 (ko) * | 2013-09-17 | 2016-11-01 | 주식회사 엘지화학 | 니트릴 고무 및 제조방법 |
-
1970
- 1970-02-24 DE DE19702008479 patent/DE2008479A1/de active Pending
- 1970-12-25 JP JP45117870A patent/JPS4921290B1/ja active Pending
-
1971
- 1971-02-16 FR FR7105137A patent/FR2078633A5/fr not_active Expired
- 1971-02-22 US US00117757A patent/US3781250A/en not_active Expired - Lifetime
- 1971-04-19 GB GB2235471A patent/GB1330058A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2078633A5 (enExample) | 1971-11-05 |
| JPS4921290B1 (enExample) | 1974-05-31 |
| GB1330058A (en) | 1973-09-12 |
| US3781250A (en) | 1973-12-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1953143C3 (de) | Tris-hydroxybenzyl-isocyanurate und deren Verwendung zum Stabilisieren von Polymeren | |
| DE69502902T2 (de) | Herstellung von bitumen/polymerzusammensetzungen und ihre verwendung | |
| DE2045574C3 (de) | Schwefelvulkanisierbare Masse | |
| DE2008479A1 (de) | Verfahren zum Vulkanisieren von Homobzw. Copoiymerisaten konjugierter Diene | |
| DE2117615A1 (de) | Inhibierung vorzeitiger Vulkanisation von Kautschuken | |
| DE69905817T2 (de) | Kautschukzusammensetzung die ein reversionsverhinderndes Mittel enthält und Reifen mit daraus hergestellter Komponente | |
| DD240203A5 (de) | Verfahren zur herstellung von bis-(2-ethylamino-4-diethylamino-s-triazin-6-yl)tetrasulfid | |
| DE1720132C3 (de) | Verfahren zur Hemmung der vorzeitigen Vulkanisation von Kautschuk | |
| DE602004007541T2 (de) | Härter, der für epdm-kautschuke geeignet ist | |
| DE1929742C3 (de) | Halogenhaltige polymere elastomere Massen | |
| DE2616613C2 (de) | Vulkanisierbare Kautschukmasse | |
| DE2136066B2 (de) | N-Sulfenyllactame und deren Verwendung | |
| DE2110844C3 (de) | Verfahren zur Inhibierung der vorzeitigen Vulkanisation von mit Schwefel vulkanisierbaren Kautschukmassen | |
| DE898675C (de) | Verfahren zum Vulkanisieren von Kautschuk | |
| DE1301482B (de) | Verfahren zum Vulkanisieren von Kautschuk | |
| DD284007A5 (de) | Verfahren zur herstellung von gemischen, bestehend aus n,n'-substituierter bis-(2,4-diamino-s-triakin-6-yl)-oligo-sulfiden | |
| DE19931043A1 (de) | Schwefel-vulkanisierbarer Butylgummi und Gummizusammensetzung, enthalted denselben | |
| EP0601303A1 (de) | Polysulfid-Verbindungen und Vulkanisationssysteme | |
| DE60127987T2 (de) | Alkylthio- und aryl(heteroyl)thio-substituierte p-phenylendiamine, deren herstellung und deren verwendung in kautschuk | |
| DE69227280T2 (de) | Für Autoreifen geeignete Kautschukzusammensetzung und ihre Herstellung | |
| DE10114025A1 (de) | Neues Vulkanisierungsmittel für Kautschuke auf Dien-Basis und Kautschukzusammensetzung mit diesem | |
| DE1136820B (de) | Verfahren zur Herstellung kautschukartiger Gemische | |
| DE852904C (de) | Verfahren zum Vulkanisieren eines synthetischen, mit Schwefel vulkanisierbaren, kautschukaehnlichen Mischpolymeren eines Butadien-1, 3-Kohlenwasserstoffs und einer Monovinylverbindung | |
| EP3587395B1 (de) | Mit ethylenisch ungesättigten gruppen modifiziertes diphenylguanidin | |
| DE4128869A1 (de) | Verfahren zur herstellung von dienkautschuk-vulkanisaten |