JPH0251429B2 - - Google Patents
Info
- Publication number
- JPH0251429B2 JPH0251429B2 JP57093446A JP9344682A JPH0251429B2 JP H0251429 B2 JPH0251429 B2 JP H0251429B2 JP 57093446 A JP57093446 A JP 57093446A JP 9344682 A JP9344682 A JP 9344682A JP H0251429 B2 JPH0251429 B2 JP H0251429B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- mmol
- epoxy resin
- acid
- epihalohydrin
- 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
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims description 38
- 239000003822 epoxy resin Substances 0.000 claims description 20
- 229920000647 polyepoxide Polymers 0.000 claims description 20
- 235000004515 gallic acid Nutrition 0.000 claims description 19
- 229940074391 gallic acid Drugs 0.000 claims description 19
- 235000015523 tannic acid Nutrition 0.000 claims description 13
- 229920002258 tannic acid Polymers 0.000 claims description 13
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 claims description 12
- 239000001263 FEMA 3042 Substances 0.000 claims description 12
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 claims description 12
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 claims description 12
- 229940033123 tannic acid Drugs 0.000 claims description 12
- 239000003444 phase transfer catalyst Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- 239000003518 caustics Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical group 0.000 claims description 3
- VUEDNLCYHKSELL-UHFFFAOYSA-N arsonium Chemical group [AsH4+] VUEDNLCYHKSELL-UHFFFAOYSA-N 0.000 claims description 2
- 150000004714 phosphonium salts Chemical group 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 18
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 10
- 125000002843 carboxylic acid group Chemical group 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000002329 infrared spectrum Methods 0.000 description 8
- 239000004593 Epoxy Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 150000008065 acid anhydrides Chemical class 0.000 description 6
- 238000007259 addition reaction Methods 0.000 description 6
- -1 glycidyl ester Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 150000004682 monohydrates Chemical class 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000003944 halohydrins Chemical class 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- WORJRXHJTUTINR-UHFFFAOYSA-N 1,4-dioxane;hydron;chloride Chemical compound Cl.C1COCCO1 WORJRXHJTUTINR-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000007965 phenolic acids Chemical class 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- AGIBHMPYXXPGAX-UHFFFAOYSA-N 2-(iodomethyl)oxirane Chemical compound ICC1CO1 AGIBHMPYXXPGAX-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- WAGFXJQAIZNSEQ-UHFFFAOYSA-M tetraphenylphosphonium chloride Chemical compound [Cl-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WAGFXJQAIZNSEQ-UHFFFAOYSA-M 0.000 description 1
- PPQRADLPLZYEKN-UHFFFAOYSA-N tritylphosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1C(C=1C=CC=CC=1)([PH3+])C1=CC=CC=C1 PPQRADLPLZYEKN-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/3218—Carbocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57093446A JPS58210078A (ja) | 1982-05-31 | 1982-05-31 | 新規エポキシ樹脂およびその製造方法 |
| US06/491,226 US4540802A (en) | 1982-05-31 | 1983-05-03 | Epoxy resin and process for preparing the same |
| EP83104564A EP0095609B1 (en) | 1982-05-31 | 1983-05-10 | Epoxy resins and process for preparing the same |
| DE8383104564T DE3368624D1 (en) | 1982-05-31 | 1983-05-10 | Epoxy resins and process for preparing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57093446A JPS58210078A (ja) | 1982-05-31 | 1982-05-31 | 新規エポキシ樹脂およびその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58210078A JPS58210078A (ja) | 1983-12-07 |
| JPH0251429B2 true JPH0251429B2 (en, 2012) | 1990-11-07 |
Family
ID=14082549
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57093446A Granted JPS58210078A (ja) | 1982-05-31 | 1982-05-31 | 新規エポキシ樹脂およびその製造方法 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4540802A (en, 2012) |
| EP (1) | EP0095609B1 (en, 2012) |
| JP (1) | JPS58210078A (en, 2012) |
| DE (1) | DE3368624D1 (en, 2012) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3571642D1 (en) * | 1984-06-29 | 1989-08-24 | Ciba Geigy Ag | Lubricant additives |
| DE3573778D1 (en) * | 1984-06-29 | 1989-11-23 | Ciba Geigy Ag | Process for the preparation of glycidyl thioethers |
| EP0431891A1 (en) * | 1989-12-06 | 1991-06-12 | Teijin Limited | Epoxy compounds, production processes thereof and cured product of the epoxy compound |
| US5364912A (en) * | 1990-09-13 | 1994-11-15 | The Dow Chemical Company | Thermoplastic resins from polyglycidyl esters containing mesogenic moieties |
| JP2010241855A (ja) * | 2009-04-01 | 2010-10-28 | Hitachi Ltd | エポキシ樹脂組成物 |
| FR2946049B1 (fr) * | 2009-05-27 | 2013-01-18 | Chaire Europ De Chimie Nouvelle Pour Un Dev Durable | Compose phenoliques naturels et leur mode d'activation pour la formulation de resines thermodurcissables |
| FR3035401B1 (fr) | 2015-04-27 | 2017-05-26 | Agronomique Inst Nat Rech | Compose a fonctions epoxydes biosource, procede de synthese d'un tel compose et son utilisation pour la preparation de resine epoxyde |
| EP3589694A4 (en) * | 2017-03-01 | 2020-11-18 | Purdue Research Foundation | COMPOSITIONS OF PRODUCT RESULTING FROM THE EPOXY-TANNIN REACTION |
| CN111040131A (zh) * | 2019-12-20 | 2020-04-21 | 中国科学院上海有机化学研究所 | 一种基于儿茶酸的环氧树脂的合成和应用 |
| CN115701284A (zh) * | 2020-03-20 | 2023-02-07 | 英格维蒂南卡罗来纳有限责任公司 | 妥尔油衍生的缩水甘油酯及其制备方法 |
| CN115703751B (zh) * | 2021-08-16 | 2024-05-07 | 广西至善新材料科技有限公司 | 没食子酸缩水甘油酯及其粘合剂制备方法 |
| CN114560996B (zh) * | 2022-03-29 | 2023-07-21 | 中海石油(中国)有限公司 | 一种利用单宁酸固化制备的可降解生物环氧树脂及其高温堵漏应用 |
| DE102022132566A1 (de) * | 2022-12-07 | 2024-06-13 | Universität Kassel, Körperschaft des öffentlichen Rechts | Biobasierte Epoxidharze sowie deren Herstellung und Verwendung als adhäsives Beschichtungsmittel |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2925426A (en) * | 1955-12-29 | 1960-02-16 | Shell Dev | Epoxy ether esters |
| US3372142A (en) * | 1964-01-31 | 1968-03-05 | Dow Chemical Co | Epoxidation process |
| DE1225661B (de) * | 1964-09-11 | 1966-09-29 | Bayer Ag | Verfahren zur Herstellung von Polyepoxydverbindungen |
| US4284573A (en) * | 1979-10-01 | 1981-08-18 | The Dow Chemical Company | Preparation of glycidyl ethers |
| JPS6011910B2 (ja) * | 1979-10-26 | 1985-03-28 | 岡村製油株式会社 | ポリカルボン酸グリシジルエステル |
| DE2947469A1 (de) * | 1979-11-24 | 1981-06-04 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von glycidylaethern ein- oder mehrwertiger phenole |
-
1982
- 1982-05-31 JP JP57093446A patent/JPS58210078A/ja active Granted
-
1983
- 1983-05-03 US US06/491,226 patent/US4540802A/en not_active Expired - Fee Related
- 1983-05-10 DE DE8383104564T patent/DE3368624D1/de not_active Expired
- 1983-05-10 EP EP83104564A patent/EP0095609B1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58210078A (ja) | 1983-12-07 |
| DE3368624D1 (en) | 1987-02-05 |
| US4540802A (en) | 1985-09-10 |
| EP0095609B1 (en) | 1986-12-30 |
| EP0095609A1 (en) | 1983-12-07 |
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