GB884033A - Process for the preparation of epoxide resins - Google Patents
Process for the preparation of epoxide resinsInfo
- Publication number
- GB884033A GB884033A GB6285/60A GB628560A GB884033A GB 884033 A GB884033 A GB 884033A GB 6285/60 A GB6285/60 A GB 6285/60A GB 628560 A GB628560 A GB 628560A GB 884033 A GB884033 A GB 884033A
- Authority
- GB
- United Kingdom
- Prior art keywords
- haloepoxyalkane
- group
- resins
- catalyst
- water
- 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
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/08—Ion-exchange resins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
- C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
-
- 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
- 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
- C08G59/12—Polycondensates containing more than one epoxy group per molecule of polycarboxylic acids 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
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
-
- 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
- C08G59/40—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 curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Epoxy Resins (AREA)
- Laminated Bodies (AREA)
- Reinforced Plastic Materials (AREA)
- Epoxy Compounds (AREA)
Abstract
Epoxy resins are prepared by heating a haloepoxyalkane with a polycarboxylic acid, or a polycarboxylic acid anhydride together with water and/or a polyhydric alcohol, in the presence of an organic catalyst of high molecular weight which is insoluble in the reaction mixture and which contains either a salt-like group or a group convertible to a salt-like group under the reaction conditions or an acid amide group. After the catalyst has been separated, excess haloepoxyalkane and volatile products are distilled off. More than 2 mols. and preferably 5-40 mols. of haloepoxyalkane are used per carboxyl group, or more than 4 mols. and preferably 10-50 mols. of haloepoxyalkane per acid anhydride group. When a polycarboxylic acid anhydride is used it may be heated with water and/or a polyhydric alcohol, with or without the haloepoxyalkane, before the addition of the catalyst. The catalyst may be wet or dry and the reaction mixture may contain up to 3% of water over and above any water present for the hydrolysis of a polycarboxylic acid anhydride. Many polycarboxylic acids, polycarboxylic acid anhydrides, haloepoxyalkanes and polyhydric alcohols are specified. The preferred polyols are those which contain one halogen atom and two hydroxyl groups and are derived p from the haloepoxyalkane by replacing the epoxide group by two hydroxyl groups. The catalysts may be the salts of cation exchange resins, anion exchange resins or their salts, mixed-bed ion exchange resins, amphoteric ion exchange resins, melamine resins, aminecured epoxy resins, polyamides or proteins. The catalyst is first graded to remove fines. In a typical example phthalic acid and epichlorohydrin are refluxed with a commercial, water-containing anion exchanger based on polystyrene and containing quaternary benzyl ammonium groups. In another example, castor oil, glycerol and phthalic anhydride are heated together to give an acid ester which is heated with epichlorohydrin in the presence of an anion exchange resin containing quaternary ammonium groups. In a similar example, the acid ester used is prepared by heating ethoxylated methylcellulose with phthalic anhydride under nitrogen. The epoxide oxygen content of the products may be increased by dehydrohalogenation using sodium hydroxide in methylene chloride or by treating the product with a further amount of epichlorohydrin by the process of this invention. The products may be bleached by organic peroxides and cured by curing agents such as, e.g. amines and acid anhydrides. They may be used as adhesives, casting resins, or lacquer resins, or for the manufacture of laminates or glass fibre reinforced materials.ALSO:Epoxy esters generally containing some halogen are prepared by heating a haloepoxyalkane with a polycarboxylic acid, or with a p polycarboxylic acid anhydride together with water and/or a polyhydric alcohol, in the presence of an organic catalyst of high molecular weight which is insoluble in the reaction mixture and which contains either a saltlike group or a group convertible to a saltlike group under the reaction conditions or an acid amide group. After the catalyst has been separated, excess haloepoxyalkane and volatile products are distilled off. More than 2 mol and preferably 5-40 mol of haloepoxyalkane are used per carboxyl group, or more than 4 mol and preferably 10-50 mol of haloepoxyalkane are used per acid anhydride group. When a polycarboxylic acid anhydride is used it may be heated with water and/or a polyhydric alcohol with or without the haloepoxyalkane before the addition of the catalyst. The catalyst may be wet or dry and the reaction mixture may contain up to 3% of water over and above any water present for the hydrolysis of a polycarboxylic acid anhydride. Many polycarboxylic acids, polycarboxylic acid anhydrides, haloepoxyalkanes and polyhydric alcohols are specified. The acids may be substituted, e.g. by ether, ester or hydroxyl groups. The preferred polyols are those containing one halogen atom and two hydroxyl groups and which are derived from the haloepoxyalkane by replacing the epoxide group by two hydroxyl groups. The catalysts may be the salts of cation exchange resins, anion exchange resins or their salts, mixed lead ion exchange resins, amphoteric ion exchange resins, melamine resins, aminecured epoxy resins, polyamides or proteins. The catalyst is first graded to remove fines. In a typical example phthalic acid and epichlorohydrin are refluxed with a commercial, water-containing anion exchanger based on polystyrene and containing quaternary benzyl ammonium groups. In another example, castor oil, glycerol and phthalic anhydride are heated together to give an acid ester which is heated with epichlorohydrin in the presence of an anion exchange resin containing quaternary ammonium groups. The epoxide oxygen content of the products may be increased by dehydrohalogenation using sodium hydroxide in methylene chloride or by treating the product with a further amount of epichlorohydrin by the process of this invention. The products may be bleached by organic peroxides and cured by curing agents such as, e.g., amines and acid anhydrides. They may be used as adhesives, casting resins, or lacquer resins, or for the manufacture of laminates or fibre glass reinforced materials.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES0265094A ES265094A1 (en) | 1960-02-23 | 1961-02-21 | Method for the production of salts of 1,4-di-2- (halogenoethylamino) -butane-2,3-diols (Machine-translation by Google Translate, not legally binding) |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEH35729A DE1165030B (en) | 1959-02-25 | 1959-02-25 | Process for the preparation of curable compounds containing epoxy groups |
Publications (1)
Publication Number | Publication Date |
---|---|
GB884033A true GB884033A (en) | 1961-12-06 |
Family
ID=7152785
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB6285/60A Expired GB884033A (en) | 1959-02-25 | 1960-02-23 | Process for the preparation of epoxide resins |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE588009A (en) |
DE (1) | DE1165030B (en) |
GB (1) | GB884033A (en) |
NL (1) | NL248735A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3251903A (en) * | 1962-11-09 | 1966-05-17 | Wyandotte Chemicals Corp | Cross-linked polyhalogenous polyester compositions prepared by reacting polyhalogenous epoxides with anhydrides |
US3254057A (en) * | 1962-11-09 | 1966-05-31 | Wyandotte Chemicals Corp | Polyhalogenous polyester compositions |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2522043A1 (en) * | 1975-05-17 | 1976-11-25 | Huels Chemische Werke Ag | LIQUID COATING AGENTS |
DE2522044C2 (en) * | 1975-05-17 | 1982-05-19 | Chemische Werke Hüls AG, 4370 Marl | Use of a liquid, low-solvent or solvent-free coating agent for the production of coatings. |
DE2522045C2 (en) * | 1975-05-17 | 1982-05-19 | Chemische Werke Hüls AG, 4370 Marl | Use of a liquid, low-solvent or solvent-free coating agent for the production of coatings |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE503552A (en) * | 1950-05-27 | |||
DE1033204B (en) * | 1953-11-23 | 1958-07-03 | Bataafsche Petroleum | Process for the production of glycidic esters |
DE944995C (en) * | 1954-07-31 | 1956-06-28 | Henkel & Cie Gmbh | Process for the production of epoxy compounds |
-
0
- NL NL248735D patent/NL248735A/xx unknown
- BE BE588009D patent/BE588009A/xx unknown
-
1959
- 1959-02-25 DE DEH35729A patent/DE1165030B/en active Pending
-
1960
- 1960-02-23 GB GB6285/60A patent/GB884033A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3251903A (en) * | 1962-11-09 | 1966-05-17 | Wyandotte Chemicals Corp | Cross-linked polyhalogenous polyester compositions prepared by reacting polyhalogenous epoxides with anhydrides |
US3254057A (en) * | 1962-11-09 | 1966-05-31 | Wyandotte Chemicals Corp | Polyhalogenous polyester compositions |
Also Published As
Publication number | Publication date |
---|---|
BE588009A (en) | 1900-01-01 |
NL248735A (en) | 1900-01-01 |
DE1165030B (en) | 1964-03-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ES486439A1 (en) | Thermosetting resinous binder compositions, their preparation, and use as coating materials. | |
ES2001053A6 (en) | Resin compositions and a process for preparing laminates therefrom. | |
NO934683L (en) | Hardenable compositions | |
GB884033A (en) | Process for the preparation of epoxide resins | |
BR8407303A (en) | A PROCESS FOR THE PREPARATION OF ESTER VINYL RESINS CONTAINING TRIAZIN GROUPS OR BOTH TRIAZIN GROUPS AS OXAZOLIN | |
ES490375A0 (en) | PROCEDURE FOR THE PRODUCTION OF COMPOSITIONS OF HARDENED POLYEPOXIDIC RESINS | |
ATE4905T1 (en) | PROCESS FOR THE MANUFACTURE OF AQUEOUS EPOXY RESIN DISPERSIONS AND THEIR USE. | |
GB858254A (en) | Improvements in the production of expanded polyamides | |
GB1086877A (en) | Process for the production of polyamides | |
US2582191A (en) | Amino salts of boric acid-aliphatic polyhydroxy carboxylic acid condensation product | |
GB376929A (en) | Process for the production of synthetic resins from alcoholamines and organic acids | |
US3711514A (en) | Highly fluorinated alkyl esters of trimellitic acid anhydride and method for their production | |
GB819191A (en) | Improvements in or relating to the production of hardenable epoxy resin compositions | |
GB1253182A (en) | ||
GB1002183A (en) | New halogen-containing glycidyl ethers | |
GB1063349A (en) | Thermoplastic epoxy polymers | |
GB910554A (en) | Improvements in or relating to the preparation of new resinous condensation products | |
CH499572A (en) | Phthalic anhydride diethylenetriamine condensates as | |
GB1284793A (en) | Production of glycidyl esters of polycarboxylic acids | |
JPS5575421A (en) | Epoxy resin composition | |
GB929034A (en) | Process for the manufacture of monomeric chloroacetaldehyde | |
GB1329190A (en) | Resins produced from the reaction of epoxides and dimethyl olpropionic acid | |
GB625203A (en) | Improvements in or relating to the manufacture of aliphatic diesters of aromatic dicarboxylic acids | |
GB822928A (en) | Moulding compositions containing epoxide resins | |
JPS5636561A (en) | Adhesive for heat-resistant resin molded product |