CA1335387C - Vulcanization activator and process for its production - Google Patents
Vulcanization activator and process for its productionInfo
- Publication number
- CA1335387C CA1335387C CA 611974 CA611974A CA1335387C CA 1335387 C CA1335387 C CA 1335387C CA 611974 CA611974 CA 611974 CA 611974 A CA611974 A CA 611974A CA 1335387 C CA1335387 C CA 1335387C
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- carboxylic acid
- component
- acid
- group
- 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 - Lifetime
Links
- 239000012936 vulcanization activator Substances 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 title 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- 150000003751 zinc Chemical class 0.000 claims abstract description 10
- 229920001971 elastomer Polymers 0.000 claims abstract description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 239000011593 sulfur Substances 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 3
- 150000007513 acids Chemical class 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 17
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 12
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 10
- 235000010233 benzoic acid Nutrition 0.000 claims description 7
- 239000005711 Benzoic acid Substances 0.000 claims description 6
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 5
- 239000011787 zinc oxide Substances 0.000 claims description 5
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 claims description 4
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 claims description 2
- 239000006227 byproduct Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 235000004416 zinc carbonate Nutrition 0.000 claims description 2
- 239000011667 zinc carbonate Substances 0.000 claims description 2
- 229910000010 zinc carbonate Inorganic materials 0.000 claims description 2
- 150000003752 zinc compounds Chemical class 0.000 claims description 2
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 claims description 2
- 229940007718 zinc hydroxide Drugs 0.000 claims description 2
- 229910021511 zinc hydroxide Inorganic materials 0.000 claims description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims 2
- 239000012467 final product Substances 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 238000005453 pelletization Methods 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract description 4
- 239000012190 activator Substances 0.000 description 13
- 238000012360 testing method Methods 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 241000282320 Panthera leo Species 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 235000021355 Stearic acid Nutrition 0.000 description 5
- -1 fatty acid salts Chemical class 0.000 description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 5
- 239000008117 stearic acid Substances 0.000 description 5
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 4
- 238000004073 vulcanization Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229920003052 natural elastomer Polymers 0.000 description 2
- 229920001194 natural rubber Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- YFONKFDEZLYQDH-OPQQBVKSSA-N N-[(1R,2S)-2,6-dimethyindan-1-yl]-6-[(1R)-1-fluoroethyl]-1,3,5-triazine-2,4-diamine Chemical compound C[C@@H](F)C1=NC(N)=NC(N[C@H]2C3=CC(C)=CC=C3C[C@@H]2C)=N1 YFONKFDEZLYQDH-OPQQBVKSSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 235000015107 ale Nutrition 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000006467 substitution reaction 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
- 238000012956 testing procedure Methods 0.000 description 1
- 238000003878 thermal aging Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229940098697 zinc laurate Drugs 0.000 description 1
- GPYYEEJOMCKTPR-UHFFFAOYSA-L zinc;dodecanoate Chemical compound [Zn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O GPYYEEJOMCKTPR-UHFFFAOYSA-L 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
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19883831883 DE3831883C1 (enrdf_load_stackoverflow) | 1988-09-20 | 1988-09-20 | |
| DEP3831883.0 | 1988-09-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1335387C true CA1335387C (en) | 1995-04-25 |
Family
ID=6363308
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 611974 Expired - Lifetime CA1335387C (en) | 1988-09-20 | 1989-09-19 | Vulcanization activator and process for its production |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0363562B1 (enrdf_load_stackoverflow) |
| JP (1) | JP2657245B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1335387C (enrdf_load_stackoverflow) |
| DE (1) | DE3831883C1 (enrdf_load_stackoverflow) |
| ES (1) | ES2061792T3 (enrdf_load_stackoverflow) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW223650B (en) * | 1993-06-14 | 1994-05-11 | Akzo Nv | Sulfur-vulcanized rubber compositions |
| JP2002371156A (ja) * | 2001-04-10 | 2002-12-26 | Yokohama Rubber Co Ltd:The | ゴム組成物 |
| JP5002194B2 (ja) * | 2006-05-31 | 2012-08-15 | 住友ゴム工業株式会社 | タイヤ用ゴム組成物およびそれを用いたタイヤ |
| JP5079261B2 (ja) * | 2006-05-31 | 2012-11-21 | 住友ゴム工業株式会社 | ゴム組成物およびそれを用いた空気入りタイヤ |
| JP4540691B2 (ja) | 2007-06-08 | 2010-09-08 | 住友ゴム工業株式会社 | タイヤ用ゴム組成物およびタイヤ |
| JP4638950B2 (ja) | 2008-09-01 | 2011-02-23 | 住友ゴム工業株式会社 | スタッドレスタイヤ用ゴム組成物及びスタッドレスタイヤ |
| JP5132606B2 (ja) * | 2009-02-23 | 2013-01-30 | 台茂高分子科學股▲ふん▼有限公司 | 硫化促進助剤 |
| JP6575464B2 (ja) * | 2016-08-29 | 2019-09-18 | 住友ゴム工業株式会社 | ゴム組成物 |
| JP6933068B2 (ja) * | 2016-09-23 | 2021-09-08 | 住友ゴム工業株式会社 | スチールコード被覆用ゴム組成物およびタイヤ |
| JP6977259B2 (ja) * | 2016-12-21 | 2021-12-08 | 住友ゴム工業株式会社 | 空気入りタイヤ |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1142195A (en) * | 1965-06-18 | 1969-02-05 | British Petroleum Co | Alkaline lubricating oil |
| GB2105345B (en) * | 1981-08-18 | 1985-04-03 | British Petroleum Co Plc | A curable rubber composition |
| EP0172410A1 (en) * | 1984-08-24 | 1986-02-26 | The Firestone Tire & Rubber Company | Method for increasing the modulus of vulcanizable rubber |
-
1988
- 1988-09-20 DE DE19883831883 patent/DE3831883C1/de not_active Expired
-
1989
- 1989-06-03 ES ES89110074T patent/ES2061792T3/es not_active Expired - Lifetime
- 1989-06-03 EP EP19890110074 patent/EP0363562B1/de not_active Expired - Lifetime
- 1989-09-19 JP JP1240927A patent/JP2657245B2/ja not_active Expired - Fee Related
- 1989-09-19 CA CA 611974 patent/CA1335387C/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH02169642A (ja) | 1990-06-29 |
| ES2061792T3 (es) | 1994-12-16 |
| JP2657245B2 (ja) | 1997-09-24 |
| EP0363562B1 (de) | 1994-02-09 |
| EP0363562A1 (de) | 1990-04-18 |
| DE3831883C1 (enrdf_load_stackoverflow) | 1989-09-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |