DE2342453A1 - Verfahren zum verhindern der vorzeitigen vulkanisation eines kautschukgemisches - Google Patents
Verfahren zum verhindern der vorzeitigen vulkanisation eines kautschukgemischesInfo
- Publication number
- DE2342453A1 DE2342453A1 DE19732342453 DE2342453A DE2342453A1 DE 2342453 A1 DE2342453 A1 DE 2342453A1 DE 19732342453 DE19732342453 DE 19732342453 DE 2342453 A DE2342453 A DE 2342453A DE 2342453 A1 DE2342453 A1 DE 2342453A1
- Authority
- DE
- Germany
- Prior art keywords
- rubber
- parts
- diene
- vulcanization
- compound
- 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
- 229920001971 elastomer Polymers 0.000 title claims description 43
- 239000005060 rubber Substances 0.000 title claims description 43
- 238000004073 vulcanization Methods 0.000 title claims description 29
- 239000000203 mixture Substances 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 11
- 230000002028 premature Effects 0.000 title claims description 10
- -1 cyclohexa-2,5-diene compound Chemical class 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 150000002430 hydrocarbons Chemical group 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 238000003490 calendering Methods 0.000 claims description 2
- 238000001125 extrusion Methods 0.000 claims description 2
- 229910000071 diazene Inorganic materials 0.000 description 23
- 239000000654 additive Substances 0.000 description 13
- 241001441571 Hiodontidae Species 0.000 description 11
- 230000000996 additive effect Effects 0.000 description 10
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 8
- 238000006731 degradation reaction Methods 0.000 description 7
- UVJHQYIOXKWHFD-UHFFFAOYSA-N cyclohexa-1,4-diene Chemical class C1C=CCC=C1 UVJHQYIOXKWHFD-UHFFFAOYSA-N 0.000 description 6
- 244000043261 Hevea brasiliensis Species 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229920003052 natural elastomer Polymers 0.000 description 4
- 229920001194 natural rubber Polymers 0.000 description 4
- 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 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- UEZWYKZHXASYJN-UHFFFAOYSA-N cyclohexylthiophthalimide Chemical compound O=C1C2=CC=CC=C2C(=O)N1SC1CCCCC1 UEZWYKZHXASYJN-UHFFFAOYSA-N 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- 229940054266 2-mercaptobenzothiazole Drugs 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000001055 chewing effect Effects 0.000 description 2
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000000463 material Substances 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
- 229920001195 polyisoprene Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000004071 soot Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000007979 thiazole derivatives Chemical class 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011787 zinc oxide Substances 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
- WELKBINNNXKQQS-UHFFFAOYSA-N 1,4-benzoquinone imine Chemical compound N=C1C=CC(=O)C=C1 WELKBINNNXKQQS-UHFFFAOYSA-N 0.000 description 1
- NPOSWZYXFPUUQW-UHFFFAOYSA-N 1-n,2-n-bis(5-methylheptan-3-yl)benzene-1,2-diamine Chemical compound CCC(C)CC(CC)NC1=CC=CC=C1NC(CC)CC(C)CC NPOSWZYXFPUUQW-UHFFFAOYSA-N 0.000 description 1
- OSTLIVYSNQFRHL-UHFFFAOYSA-N 1-n-cyclohexyl-4-n-phenylcyclohexa-2,5-diene-1,4-diimine Chemical compound C1CCCCC1N=C(C=C1)C=CC1=NC1=CC=CC=C1 OSTLIVYSNQFRHL-UHFFFAOYSA-N 0.000 description 1
- DTYANCALLQJURE-UHFFFAOYSA-N 4-phenyliminocyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=NC1=CC=CC=C1 DTYANCALLQJURE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 229920004940 NATSYN® Polymers 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000003111 delayed effect 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
- 229920003244 diene elastomer Polymers 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000010059 sulfur vulcanization Methods 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
- ZUBNXRHITOZMOO-UHFFFAOYSA-N zinc;octadecanoic acid;oxygen(2-) Chemical compound [O-2].[Zn+2].CCCCCCCCCCCCCCCCCC(O)=O ZUBNXRHITOZMOO-UHFFFAOYSA-N 0.000 description 1
- 238000013316 zoning Methods 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3935472A GB1422641A (en) | 1972-08-23 | 1972-08-23 | Retarding rubber vulcanization |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2342453A1 true DE2342453A1 (de) | 1974-04-04 |
Family
ID=10409103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732342453 Pending DE2342453A1 (de) | 1972-08-23 | 1973-08-22 | Verfahren zum verhindern der vorzeitigen vulkanisation eines kautschukgemisches |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3882186A (enExample) |
| JP (1) | JPS4986429A (enExample) |
| CA (1) | CA996293A (enExample) |
| DE (1) | DE2342453A1 (enExample) |
| FR (1) | FR2331247A7 (enExample) |
| GB (1) | GB1422641A (enExample) |
| IT (1) | IT990298B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4968843A (en) * | 1990-03-08 | 1990-11-06 | The Goodyear Tire & Rubber Company | Preparation of a N-substituted phenylenediamine |
| US5068439A (en) * | 1990-03-08 | 1991-11-26 | The Goodyear Tire & Rubber Company | N-substituted phenylenediamine compounds |
| US5470440A (en) * | 1994-04-19 | 1995-11-28 | Betz Laboratories, Inc. | Method for inhibiting vinyl aromatic monomer polymerization |
| KR100551876B1 (ko) | 1997-10-20 | 2006-02-14 | 플렉시스 아메리카, 엘.피. | 고무첨가제 퀴논 디이민 |
| US6533859B2 (en) | 2000-05-26 | 2003-03-18 | Flexsys America L.P. | Surface treated carbon black having improved dispersability in rubber and compositions of rubber therefrom having improved processability, rheological and dynamic mechanical properties |
| US7718722B2 (en) * | 2000-11-21 | 2010-05-18 | Flexsys America L.P. | Alkylthio- and aryl(heteroyl)thio-substituted p-phenylenediamines, their manufacture and their use in rubber |
| JP5017703B2 (ja) * | 2007-05-16 | 2012-09-05 | 住友ゴム工業株式会社 | ビードエイペックスおよびタイヤ |
| FR2966373B1 (fr) | 2010-10-21 | 2014-03-07 | Michelin Soc Tech | Procede et dispositif de regulation d'un moyen d'extrusion d'un melange d'elastomere comportant des produits vulcanisants |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2170191A (en) * | 1934-05-31 | 1939-08-22 | Us Rubber Co | Treatment of rubber |
| US3032520A (en) * | 1953-11-25 | 1962-05-01 | Robert F Shaw | Antiozidants for rubber compositions |
| NL269405A (enExample) * | 1960-09-21 |
-
1972
- 1972-08-23 GB GB3935472A patent/GB1422641A/en not_active Expired
-
1973
- 1973-08-14 CA CA178,756A patent/CA996293A/en not_active Expired
- 1973-08-22 DE DE19732342453 patent/DE2342453A1/de active Pending
- 1973-08-22 IT IT52130/73A patent/IT990298B/it active
- 1973-08-22 JP JP48094250A patent/JPS4986429A/ja active Pending
- 1973-08-22 FR FR7330410A patent/FR2331247A7/fr not_active Expired
- 1973-08-23 US US390740A patent/US3882186A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB1422641A (en) | 1976-01-28 |
| US3882186A (en) | 1975-05-06 |
| IT990298B (it) | 1975-06-20 |
| FR2331247A7 (fr) | 1977-06-03 |
| JPS4986429A (enExample) | 1974-08-19 |
| CA996293A (en) | 1976-08-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |