CA1102488A - Method for the preparation of liquid epoxy resins - Google Patents
Method for the preparation of liquid epoxy resinsInfo
- Publication number
- CA1102488A CA1102488A CA267,426A CA267426A CA1102488A CA 1102488 A CA1102488 A CA 1102488A CA 267426 A CA267426 A CA 267426A CA 1102488 A CA1102488 A CA 1102488A
- Authority
- CA
- Canada
- Prior art keywords
- alkali metal
- epichlorohydrin
- metal hydroxide
- reaction
- bisphenol
- 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
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 5
- 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 claims abstract description 32
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims abstract description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 20
- 229940106691 bisphenol a Drugs 0.000 claims abstract description 16
- 239000012429 reaction media Substances 0.000 claims abstract description 14
- 239000007864 aqueous solution Substances 0.000 claims abstract description 10
- 238000009835 boiling Methods 0.000 claims abstract description 8
- 238000004064 recycling Methods 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- 239000006227 byproduct Substances 0.000 claims description 6
- 238000004821 distillation Methods 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 4
- 229910001514 alkali metal chloride Inorganic materials 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 235000011118 potassium hydroxide Nutrition 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 235000011121 sodium hydroxide Nutrition 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 12
- 239000000460 chlorine Substances 0.000 abstract description 12
- 229910052801 chlorine Inorganic materials 0.000 abstract description 12
- 239000004593 Epoxy Substances 0.000 abstract description 8
- 239000000243 solution Substances 0.000 abstract description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 41
- 229920005989 resin Polymers 0.000 description 13
- 239000011347 resin Substances 0.000 description 13
- 239000003822 epoxy resin Substances 0.000 description 8
- 229920000647 polyepoxide Polymers 0.000 description 8
- 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 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003513 alkali Substances 0.000 description 3
- 229910000000 metal hydroxide Inorganic materials 0.000 description 3
- 150000004692 metal hydroxides Chemical class 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- UWLINSANVPZJBA-UHFFFAOYSA-N 2-(chloromethyl)oxirane hydrate Chemical compound O.ClCC1CO1 UWLINSANVPZJBA-UHFFFAOYSA-N 0.000 description 1
- 241000905957 Channa melasoma Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 150000002924 oxiranes Chemical group 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- 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
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
- C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
- C08G59/063—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols with epihalohydrins
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT30496-A/75 | 1975-12-19 | ||
| IT30496/75A IT1051400B (it) | 1975-12-19 | 1975-12-19 | Procedimento perfezionato per la preparazione di resine epossidiche liquide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1102488A true CA1102488A (en) | 1981-06-02 |
Family
ID=11229852
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA267,426A Expired CA1102488A (en) | 1975-12-19 | 1976-12-08 | Method for the preparation of liquid epoxy resins |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4132718A (ref) |
| JP (1) | JPS5290598A (ref) |
| BR (1) | BR7608523A (ref) |
| CA (1) | CA1102488A (ref) |
| DE (1) | DE2656865A1 (ref) |
| ES (1) | ES454387A1 (ref) |
| FR (1) | FR2335545A1 (ref) |
| GB (1) | GB1529910A (ref) |
| IT (1) | IT1051400B (ref) |
| MX (1) | MX143965A (ref) |
| NL (1) | NL7613758A (ref) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2947469A1 (de) * | 1979-11-24 | 1981-06-04 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von glycidylaethern ein- oder mehrwertiger phenole |
| KR910001133B1 (ko) * | 1982-04-28 | 1991-02-25 | 스미또모 가까구 고교 가부시끼가이샤 | 1가 또는 다가 페놀의 글리시딜 에테르의 제조방법 |
| US4447598A (en) * | 1983-04-07 | 1984-05-08 | The Dow Chemical Company | Method of preparing epoxy resins having low hydrolyzable chloride contents |
| US4558116A (en) * | 1985-03-04 | 1985-12-10 | The Dow Chemical Company | Process for preparing relatively high molecular weight epoxy resins |
| ES2059307T3 (es) * | 1985-12-13 | 1994-11-16 | Ciba Geigy Ag | Procedimiento para la preparacion de compuestos glicidilo. |
| US4751280A (en) * | 1986-10-14 | 1988-06-14 | The Dow Chemical Company | Preparation of epoxy resins and aftertreatment of resin via drying, filtering and washing |
| CA1293837C (en) * | 1986-10-14 | 1991-12-31 | Ha Q. Pham | Preparation of epoxy resins |
| JPH0759616B2 (ja) * | 1987-04-10 | 1995-06-28 | 住友化学工業株式会社 | エポキシ樹脂の製造方法 |
| US4785061A (en) * | 1987-08-13 | 1988-11-15 | The Dow Chemical Company | Method for reducing the aliphatic halide content of epoxy resins using a solvent mixture including a polar aprotic solvent |
| US4778863A (en) * | 1987-08-13 | 1988-10-18 | The Dow Chemical Company | Preparation of epoxy resins having low undesirable halogen content |
| US4877857A (en) * | 1988-05-05 | 1989-10-31 | The Dow Chemical Company | Preparation of epoxy resins |
| JP2723943B2 (ja) * | 1988-12-28 | 1998-03-09 | 三井化学株式会社 | 高純度多価フェノールポリグリシジルエーテルの製造方法 |
| US5310955A (en) * | 1991-01-18 | 1994-05-10 | The Dow Chemical Company | Vertical continuous reactor and process for liquid epoxy resin |
| US5576362A (en) * | 1992-04-20 | 1996-11-19 | Denki Kagaku Kogyo Kabushiki Kaisha | Insulating material and a circuit substrate in use thereof |
| CN105131252A (zh) * | 2015-10-12 | 2015-12-09 | 安徽嘉蓝新材料有限公司 | 一步法生产液态环氧树脂的方法 |
| KR101780350B1 (ko) * | 2016-03-28 | 2017-09-21 | 한국화학연구원 | 분리막 모듈을 포함하는 반응장치를 이용한 에폭시 수지 제조방법 |
| CN109280152B (zh) * | 2018-09-10 | 2021-06-08 | 南亚电子材料(昆山)有限公司 | 一种高纯度双酚a型液态环氧树脂生产工艺 |
| CN116375976A (zh) * | 2021-12-24 | 2023-07-04 | 南通星辰合成材料有限公司 | 一种液态环氧树脂的精制补加碱方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2995583A (en) * | 1961-08-08 | Method for preparation of glycidyl | ||
| NL191641A (ref) * | 1953-10-19 | |||
| GB785415A (ref) * | 1955-01-31 | |||
| US2921049A (en) * | 1955-09-16 | 1960-01-12 | Reichhold Chemicals Inc | Epoxy resin and process of making and curing the same |
| US3069434A (en) * | 1959-06-16 | 1962-12-18 | Union Carbide Corp | Process of producing polyglycidyl ethers of polyhydric phenols |
-
1975
- 1975-12-19 IT IT30496/75A patent/IT1051400B/it active
-
1976
- 1976-12-07 US US05/748,345 patent/US4132718A/en not_active Expired - Lifetime
- 1976-12-08 CA CA267,426A patent/CA1102488A/en not_active Expired
- 1976-12-10 NL NL7613758A patent/NL7613758A/xx not_active Application Discontinuation
- 1976-12-13 MX MX167371A patent/MX143965A/es unknown
- 1976-12-15 DE DE19762656865 patent/DE2656865A1/de not_active Withdrawn
- 1976-12-15 GB GB52348/76A patent/GB1529910A/en not_active Expired
- 1976-12-17 FR FR7638120A patent/FR2335545A1/fr active Granted
- 1976-12-17 BR BR7608523A patent/BR7608523A/pt unknown
- 1976-12-17 JP JP15276876A patent/JPS5290598A/ja active Granted
- 1976-12-18 ES ES454387A patent/ES454387A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US4132718A (en) | 1979-01-02 |
| ES454387A1 (es) | 1977-12-16 |
| FR2335545A1 (fr) | 1977-07-15 |
| BR7608523A (pt) | 1977-12-20 |
| IT1051400B (it) | 1981-04-21 |
| DE2656865A1 (de) | 1977-06-30 |
| NL7613758A (nl) | 1977-06-21 |
| FR2335545B1 (ref) | 1981-05-29 |
| JPS5290598A (en) | 1977-07-29 |
| GB1529910A (en) | 1978-10-25 |
| JPS5336000B2 (ref) | 1978-09-29 |
| MX143965A (es) | 1981-08-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1102488A (en) | Method for the preparation of liquid epoxy resins | |
| US3121727A (en) | Synthesis of glycidyl ethers of polyhydric phenols | |
| AU601597B2 (en) | Preparation of epoxy resins having low undesirable halogen content | |
| EP1298154B1 (en) | Process for preparing epoxy resin | |
| EP0103282B1 (en) | A process for preparing glycidyl derivatives of compounds having at least one aromatic hydroxyl group or aromatic amine group | |
| US2848426A (en) | Polyerpoxy polyethers, their preparation and polymers | |
| KR910001133B1 (ko) | 1가 또는 다가 페놀의 글리시딜 에테르의 제조방법 | |
| US4624975A (en) | Process for stabilizing the hydrolyzable chloride content in epoxy resins | |
| US2902471A (en) | Epoxy ethers, their polymers and derivatives | |
| JP2655179B2 (ja) | 第四ピペリジニウム塩を含有するエポキシ樹脂組成物 | |
| EP0214722B1 (en) | Brominated hydroxyaromatic compounds | |
| JPH0245630B2 (ref) | ||
| EP0579301A2 (en) | Process for producing biphenol skeleton-containing epoxy resins | |
| US4672103A (en) | Non-sintering epoxy resins prepared from triglycidyl ethers and epihalohydrins | |
| US4137220A (en) | Preparation of novolak epoxy resins | |
| US5077375A (en) | Glycidyl ethers of phenolic compounds and process for producing the same | |
| JPH10147629A (ja) | エポキシ樹脂、エポキシ樹脂組成物及びその硬化物 | |
| JPH09268220A (ja) | エポキシ樹脂の製造方法、エポキシ樹脂組成物及びその硬化物 | |
| JP2004010877A (ja) | 結晶性エポキシ樹脂、及びその製法 | |
| KR20020031316A (ko) | 에폭시 수지 조성물 및 그의 제조 방법 | |
| JP3379048B2 (ja) | 多官能エポキシ樹脂及びその製造方法 | |
| US2914507A (en) | Epoxy ethers of polyhydroxy-polyhydrocarbyl-substituted benzenes and their polymers | |
| JP2000273144A (ja) | エポキシ樹脂の製造方法 | |
| US3325452A (en) | Preparation of glycidyl polyethers | |
| JPH066616B2 (ja) | ジシクロペンタジエン変性エポキシ樹脂の製造法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |