DE2225279C2 - - Google Patents
Info
- Publication number
- DE2225279C2 DE2225279C2 DE2225279A DE2225279A DE2225279C2 DE 2225279 C2 DE2225279 C2 DE 2225279C2 DE 2225279 A DE2225279 A DE 2225279A DE 2225279 A DE2225279 A DE 2225279A DE 2225279 C2 DE2225279 C2 DE 2225279C2
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- radicals
- phenyl
- solution
- alkyl radicals
- 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
- -1 naphthyl radical Chemical group 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 230000032683 aging Effects 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 11
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims 1
- 150000005840 aryl radicals Chemical class 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- JTTMYKSFKOOQLP-UHFFFAOYSA-N 4-hydroxydiphenylamine Chemical compound C1=CC(O)=CC=C1NC1=CC=CC=C1 JTTMYKSFKOOQLP-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- LDJCDKGEPCWUSZ-UHFFFAOYSA-N (4-anilinophenyl) prop-2-enoate Chemical compound C1=CC(OC(=O)C=C)=CC=C1NC1=CC=CC=C1 LDJCDKGEPCWUSZ-UHFFFAOYSA-N 0.000 description 3
- ZBVPQJRFYUVYHF-KHPPLWFESA-N (z)-4-(4-anilinophenoxy)-4-oxobut-2-enoic acid Chemical compound C1=CC(OC(=O)\C=C/C(=O)O)=CC=C1NC1=CC=CC=C1 ZBVPQJRFYUVYHF-KHPPLWFESA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- ZDXJANSCJILDSA-UHFFFAOYSA-N (4-anilinophenyl) 2-methylprop-2-enoate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1NC1=CC=CC=C1 ZDXJANSCJILDSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- BRHSUWMWYHHOOM-UHFFFAOYSA-N OC(C(C(C=C1)=CC=C1NC1=CC=CC=C1)=CC1=CC=CC=C1)=O Chemical compound OC(C(C(C=C1)=CC=C1NC1=CC=CC=C1)=CC1=CC=CC=C1)=O BRHSUWMWYHHOOM-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 230000003712 anti-aging effect Effects 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- DPZZNKWSRUQJJA-UHFFFAOYSA-N (4-anilino-2,5-dimethylphenyl) 2-methylprop-2-enoate Chemical compound C1=C(C)C(OC(=O)C(=C)C)=CC(C)=C1NC1=CC=CC=C1 DPZZNKWSRUQJJA-UHFFFAOYSA-N 0.000 description 1
- TXMZCFYNKWYSAH-UHFFFAOYSA-N (4-anilino-2-methylphenyl) 2-methylprop-2-enoate Chemical compound C1=C(C)C(OC(=O)C(=C)C)=CC=C1NC1=CC=CC=C1 TXMZCFYNKWYSAH-UHFFFAOYSA-N 0.000 description 1
- MVFGWFHOYQLBLT-UHFFFAOYSA-N (4-anilino-2-methylphenyl) prop-2-enoate Chemical compound C1=C(OC(=O)C=C)C(C)=CC(NC=2C=CC=CC=2)=C1 MVFGWFHOYQLBLT-UHFFFAOYSA-N 0.000 description 1
- KRUPFVXKQJQMIA-UHFFFAOYSA-N (4-anilino-3-methylphenyl) 2-methylprop-2-enoate Chemical compound CC1=CC(OC(=O)C(=C)C)=CC=C1NC1=CC=CC=C1 KRUPFVXKQJQMIA-UHFFFAOYSA-N 0.000 description 1
- CEJJSYMLNNWSMY-UHFFFAOYSA-N (4-anilino-3-methylphenyl) prop-2-enoate Chemical compound CC1=CC(OC(=O)C=C)=CC=C1NC1=CC=CC=C1 CEJJSYMLNNWSMY-UHFFFAOYSA-N 0.000 description 1
- WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 1
- FKEQORYYGYEEPF-UHFFFAOYSA-N 2-methyl-4-(4-methylanilino)phenol Chemical compound C1=CC(C)=CC=C1NC1=CC=C(O)C(C)=C1 FKEQORYYGYEEPF-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- LLXKFGLNLPWYSD-UHFFFAOYSA-N 4-(2,4-dimethylanilino)phenol Chemical compound CC1=CC(C)=CC=C1NC1=CC=C(O)C=C1 LLXKFGLNLPWYSD-UHFFFAOYSA-N 0.000 description 1
- YYWAQXIJPIVGSG-UHFFFAOYSA-N 4-(2-methoxyanilino)phenol Chemical compound COC1=CC=CC=C1NC1=CC=C(O)C=C1 YYWAQXIJPIVGSG-UHFFFAOYSA-N 0.000 description 1
- YFEJFIBZPXJRSI-UHFFFAOYSA-N 4-(2-methylanilino)phenol Chemical compound CC1=CC=CC=C1NC1=CC=C(O)C=C1 YFEJFIBZPXJRSI-UHFFFAOYSA-N 0.000 description 1
- WSUOJSHPZXGQFO-UHFFFAOYSA-N 4-(4-ethoxyanilino)phenol Chemical compound C1=CC(OCC)=CC=C1NC1=CC=C(O)C=C1 WSUOJSHPZXGQFO-UHFFFAOYSA-N 0.000 description 1
- VNBIMUUJZMODGN-UHFFFAOYSA-N 4-(4-methoxyanilino)-3-methylphenol Chemical compound C1=CC(OC)=CC=C1NC1=CC=C(O)C=C1C VNBIMUUJZMODGN-UHFFFAOYSA-N 0.000 description 1
- FINAQCQAJZNKLH-UHFFFAOYSA-N 4-(4-methoxyanilino)phenol Chemical compound C1=CC(OC)=CC=C1NC1=CC=C(O)C=C1 FINAQCQAJZNKLH-UHFFFAOYSA-N 0.000 description 1
- PJCNSVHWHHVSMK-UHFFFAOYSA-N 4-(4-methylanilino)phenol Chemical compound C1=CC(C)=CC=C1NC1=CC=C(O)C=C1 PJCNSVHWHHVSMK-UHFFFAOYSA-N 0.000 description 1
- YJXDPMKIBPWEMX-UHFFFAOYSA-N 4-(4-propan-2-ylanilino)phenol Chemical compound C1=CC(C(C)C)=CC=C1NC1=CC=C(O)C=C1 YJXDPMKIBPWEMX-UHFFFAOYSA-N 0.000 description 1
- PUYVXGYHLVKSKH-UHFFFAOYSA-N 4-[4-(dimethylamino)anilino]phenol Chemical compound C1=CC(N(C)C)=CC=C1NC1=CC=C(O)C=C1 PUYVXGYHLVKSKH-UHFFFAOYSA-N 0.000 description 1
- DWTQJOQIMHWZSM-UHFFFAOYSA-N 4-anilino-2,5-dimethylphenol Chemical compound C1=C(O)C(C)=CC(NC=2C=CC=CC=2)=C1C DWTQJOQIMHWZSM-UHFFFAOYSA-N 0.000 description 1
- BFKNOGJONDIQHG-UHFFFAOYSA-N 4-anilino-2-methylphenol Chemical compound C1=C(O)C(C)=CC(NC=2C=CC=CC=2)=C1 BFKNOGJONDIQHG-UHFFFAOYSA-N 0.000 description 1
- DYLJVDHAFMAECU-UHFFFAOYSA-N 4-anilino-3-methylphenol Chemical compound CC1=CC(O)=CC=C1NC1=CC=CC=C1 DYLJVDHAFMAECU-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GVYTYVOADQGZNQ-UHFFFAOYSA-N [2-methyl-4-(4-methylanilino)phenyl] 2-methylprop-2-enoate Chemical compound C1=C(C)C(OC(=O)C(=C)C)=CC=C1NC1=CC=C(C)C=C1 GVYTYVOADQGZNQ-UHFFFAOYSA-N 0.000 description 1
- NCRHFBNNJVKMMD-UHFFFAOYSA-N [4-(2-methylanilino)phenyl] 2-methylprop-2-enoate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1NC1=CC=CC=C1C NCRHFBNNJVKMMD-UHFFFAOYSA-N 0.000 description 1
- WDPQRKLGRTUMFO-UHFFFAOYSA-N [4-(4-methoxyanilino)-3-methylphenyl] 2-methylprop-2-enoate Chemical compound C1=CC(OC)=CC=C1NC1=CC=C(OC(=O)C(C)=C)C=C1C WDPQRKLGRTUMFO-UHFFFAOYSA-N 0.000 description 1
- WSFPXOFLXFRKOY-UHFFFAOYSA-N [4-(4-methylanilino)phenyl] 2-methylprop-2-enoate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1NC1=CC=C(C)C=C1 WSFPXOFLXFRKOY-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229940082150 encore Drugs 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F22/10—Esters
- C08F22/12—Esters of phenols or saturated alcohols
- C08F22/22—Esters containing nitrogen
-
- 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
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/153,449 US3953411A (en) | 1971-06-15 | 1971-06-15 | Age resistant polymers of 4-(arylamino)aryl esters of α,β unsaturated carboxylic acids |
| US00153446A US3817916A (en) | 1971-06-15 | 1971-06-15 | Oxidation resistant polymeric compositions prepared from 3 - n-(4' - anilinophenyl)amino - 2-hydroxypropyl methacrylate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2225279A1 DE2225279A1 (de) | 1972-12-21 |
| DE2225279C2 true DE2225279C2 (enrdf_load_stackoverflow) | 1987-12-23 |
Family
ID=26850557
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722225279 Granted DE2225279A1 (de) | 1971-06-15 | 1972-05-24 | Alterungsschutzmittel |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5515488B2 (enrdf_load_stackoverflow) |
| AR (1) | AR195670A1 (enrdf_load_stackoverflow) |
| AU (1) | AU461115B2 (enrdf_load_stackoverflow) |
| BE (1) | BE784694A (enrdf_load_stackoverflow) |
| CA (1) | CA993147A (enrdf_load_stackoverflow) |
| DE (1) | DE2225279A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2142370A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1402845A (enrdf_load_stackoverflow) |
| NL (1) | NL173962C (enrdf_load_stackoverflow) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5127278B2 (enrdf_load_stackoverflow) * | 1972-06-30 | 1976-08-11 | ||
| US4804028A (en) * | 1986-03-05 | 1989-02-14 | The Goodyear Tire & Rubber Company | Non-staining vulcanized elastomeric composition and tires having sidewalls comprising said composition |
| US5049625A (en) * | 1990-03-08 | 1991-09-17 | The Goodyear Tire & Rubber Company | Polymeric diphenyldiamines |
| CN109415454A (zh) * | 2016-07-06 | 2019-03-01 | 思美定株式会社 | 固化性组合物及产品 |
| CN113956538A (zh) * | 2020-07-20 | 2022-01-21 | 北京化工大学 | 一种新型防老剂及其制备方法与应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1457152A (fr) * | 1964-12-08 | 1966-07-08 | Bayer Ag | Procédé de préparation de phénols contenant des groupes insaturés |
| GB1307409A (en) * | 1969-06-23 | 1973-02-21 | Goodyear Tire & Rubber | Age resisters and age resistant polymeric compositions |
-
1972
- 1972-05-10 AU AU42134/72A patent/AU461115B2/en not_active Expired
- 1972-05-12 CA CA141,947A patent/CA993147A/en not_active Expired
- 1972-05-18 AR AR242060A patent/AR195670A1/es active
- 1972-05-24 DE DE19722225279 patent/DE2225279A1/de active Granted
- 1972-06-08 FR FR7220590A patent/FR2142370A5/fr not_active Expired
- 1972-06-09 BE BE784694A patent/BE784694A/xx not_active IP Right Cessation
- 1972-06-13 JP JP5894172A patent/JPS5515488B2/ja not_active Expired
- 1972-06-15 GB GB967775A patent/GB1402845A/en not_active Expired
- 1972-06-15 NL NLAANVRAGE7208202,A patent/NL173962C/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU4213472A (en) | 1973-11-15 |
| JPS4815988A (enrdf_load_stackoverflow) | 1973-02-28 |
| AU461115B2 (en) | 1975-05-15 |
| NL173962C (nl) | 1984-04-02 |
| AR195670A1 (es) | 1973-10-31 |
| NL173962B (nl) | 1983-11-01 |
| FR2142370A5 (enrdf_load_stackoverflow) | 1973-01-26 |
| GB1402845A (en) | 1975-08-13 |
| CA993147A (en) | 1976-07-13 |
| JPS5515488B2 (enrdf_load_stackoverflow) | 1980-04-24 |
| DE2225279A1 (de) | 1972-12-21 |
| NL7208202A (enrdf_load_stackoverflow) | 1972-12-19 |
| BE784694A (fr) | 1972-10-02 |
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