GB888945A - Process for the preparation of epoxide resins - Google Patents
Process for the preparation of epoxide resinsInfo
- Publication number
- GB888945A GB888945A GB827960A GB827960A GB888945A GB 888945 A GB888945 A GB 888945A GB 827960 A GB827960 A GB 827960A GB 827960 A GB827960 A GB 827960A GB 888945 A GB888945 A GB 888945A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- catalyst
- haloepoxyalkane
- phenolic hydroxyl
- exchange resin
- 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
- 229920000647 polyepoxide Polymers 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- 239000003054 catalyst Substances 0.000 abstract 6
- 235000013824 polyphenols Nutrition 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract 2
- 150000001450 anions Chemical class 0.000 abstract 2
- 238000001914 filtration Methods 0.000 abstract 2
- 229920000570 polyether Polymers 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 abstract 1
- UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-UHFFFAOYSA-N 0.000 abstract 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 abstract 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 abstract 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 abstract 1
- 239000004793 Polystyrene Substances 0.000 abstract 1
- 229920003180 amino resin Polymers 0.000 abstract 1
- 239000003957 anion exchange resin Substances 0.000 abstract 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical group NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 239000003729 cation exchange resin Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000003700 epoxy group Chemical group 0.000 abstract 1
- 239000003822 epoxy resin Substances 0.000 abstract 1
- 238000004508 fractional distillation Methods 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000003456 ion exchange resin Substances 0.000 abstract 1
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 1
- 150000002605 large molecules Chemical class 0.000 abstract 1
- -1 methyl isobutyl ketone peroxide Chemical class 0.000 abstract 1
- 238000006396 nitration reaction Methods 0.000 abstract 1
- 150000001451 organic peroxides Chemical class 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- 239000004848 polyfunctional curative Substances 0.000 abstract 1
- 150000008442 polyphenolic compounds Chemical class 0.000 abstract 1
- 229920002223 polystyrene Polymers 0.000 abstract 1
- 239000012254 powdered material Substances 0.000 abstract 1
- 102000004169 proteins and genes Human genes 0.000 abstract 1
- 108090000623 proteins and genes Proteins 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 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
- C08G59/02—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
-
- 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
- C08G59/3236—Heterocylic compounds
- C08G59/3245—Heterocylic compounds containing only nitrogen as a heteroatom
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)
Abstract
888,945. Preparation of polyepoxy-polyethers. HENKEL & CIE G.m.b.H. March 9, 1960 [March 13, 1959; June 20, 1959], No. 8279/60. Class 2 (3). [Also in Group IV(a)] Polyepoxy-polyethers are prepared by reacting, at elevated temperature, compounds containing more than one phenolic hydroxyl group and one or no carboxyl group with a haloepoxyalkane containing a halogen atom adjacent to the epoxy group, said haloepoxyalkane being used in an amount of more than 2 mol per phenolic hydroxyl group, in the presence of a catalyst consisting of an organic high molecular weight compound insoluble in the reaction mixture, said catalyst containing either a saltlike group, or a group which is converted into a saltlike group under the reaction conditions, or an acid amide group. After separation of the catalyst excess haloepoxyalkane and volatile reaction products are distilled off. The catalyst may be removed by nitration. The haloepoxyalkane is preferably used in an. amount of from 5 to 40 mol per phenolic hydroxyl group. The catalyst may be the salt of an anion or a cation exchange resin, or an amphoteric ion exchange resin, an anion exchange resin as the free base, an aminoplast, a polyamide, an epoxide resin cured with a basic hardener, or a protein. It is preferably used in a granular form from which finely powdered material has been removed to ease filtration. It may or may not contain water. Examples are given of the polyphenols and of the haloepoxyalkanes. The products may be bleached with up to 1% by weight of an organic peroxide, e.g. methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide or cyclohexanone peroxide. In a typical example resorcinol and epichlorohydrin are heated under reflux with a water-containing, strongly basic anion exchanger based on polystyrene which contains quaternary benzylammonium groups. After filtration to remove the catalyst and fractional distillation under reduced pressure the product was almost pure resorcinol diglycidyl ether.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEH35867A DE1120140B (en) | 1959-03-13 | 1959-03-13 | Process for the preparation of curable compounds containing epoxy groups |
| DEH48117A DE1180373B (en) | 1963-01-31 | 1963-01-31 | Process for the production of a resin component containing glycidyl residues |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB888945A true GB888945A (en) | 1962-02-07 |
Family
ID=25979544
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB827960A Expired GB888945A (en) | 1959-03-13 | 1960-03-09 | Process for the preparation of epoxide resins |
| GB4718163A Expired GB996724A (en) | 1959-03-13 | 1963-11-29 | Improvements in and relating to hardenable polyepoxides |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4718163A Expired GB996724A (en) | 1959-03-13 | 1963-11-29 | Improvements in and relating to hardenable polyepoxides |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT242961B (en) |
| BE (2) | BE643162A (en) |
| CH (1) | CH432007A (en) |
| DE (1) | DE1120140B (en) |
| GB (2) | GB888945A (en) |
| NL (3) | NL125271C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3336342A (en) * | 1963-03-21 | 1967-08-15 | Bayer Ag | Process for preparing glycidyl ethers of polyhydric phenols |
| WO2011084304A1 (en) | 2009-12-16 | 2011-07-14 | Dow Global Technologies Llc | Production of epoxy resins using improved ion exchange resin catalysts |
-
0
- BE BE588543D patent/BE588543A/xx unknown
- NL NL302360D patent/NL302360A/xx unknown
- NL NL249323D patent/NL249323A/xx unknown
- NL NL125271D patent/NL125271C/xx active
-
1959
- 1959-03-13 DE DEH35867A patent/DE1120140B/en active Pending
-
1960
- 1960-03-09 GB GB827960A patent/GB888945A/en not_active Expired
-
1963
- 1963-11-29 GB GB4718163A patent/GB996724A/en not_active Expired
-
1964
- 1964-01-29 CH CH103064A patent/CH432007A/en unknown
- 1964-01-30 BE BE643162D patent/BE643162A/xx unknown
- 1964-01-30 AT AT73664A patent/AT242961B/en active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3336342A (en) * | 1963-03-21 | 1967-08-15 | Bayer Ag | Process for preparing glycidyl ethers of polyhydric phenols |
| WO2011084304A1 (en) | 2009-12-16 | 2011-07-14 | Dow Global Technologies Llc | Production of epoxy resins using improved ion exchange resin catalysts |
| JP2013514434A (en) * | 2009-12-16 | 2013-04-25 | ダウ グローバル テクノロジーズ エルエルシー | Production of epoxy resins using improved ion exchange resin catalysts. |
| US8742055B2 (en) | 2009-12-16 | 2014-06-03 | Dow Global Technologies Llc | Production of epoxy resins using improved ion exchange resin catalysts |
Also Published As
| Publication number | Publication date |
|---|---|
| NL249323A (en) | |
| NL302360A (en) | |
| DE1120140B (en) | 1961-12-21 |
| AT242961B (en) | 1965-10-11 |
| CH432007A (en) | 1967-03-15 |
| BE588543A (en) | |
| GB996724A (en) | 1965-06-30 |
| NL125271C (en) | |
| BE643162A (en) | 1964-07-30 |
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