GB648959A - Improvements in or relating to the preparation of esters of 2,3-epoxy propanol and to polymerisation products thereof - Google Patents
Improvements in or relating to the preparation of esters of 2,3-epoxy propanol and to polymerisation products thereofInfo
- Publication number
- GB648959A GB648959A GB24626/46A GB2462646A GB648959A GB 648959 A GB648959 A GB 648959A GB 24626/46 A GB24626/46 A GB 24626/46A GB 2462646 A GB2462646 A GB 2462646A GB 648959 A GB648959 A GB 648959A
- Authority
- GB
- United Kingdom
- Prior art keywords
- esters
- epoxy
- acid
- acids
- vinyl
- 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
-
- 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
Abstract
Esters of 2,3-epoxypropanol obtained by reacting an epihalohydrin with an alkali metal salt of an acid having the formula R-CH= CR1-COOH, wherein R is hydrogen or a monovalent organic radical and R1 is hydrogen, a halogen atom or a monovalent organic radical (see Group IV (b)), may be polymerized either alone or with other polymerizable compounds and particularly with vinyl and vinylidene compounds, e.g. with the methyl, ethyl and octyl esters of acrylic, methacrylic and alphachloroacrylic esters and the amides of these acids, e.g. acrylamide and methacrylamide; styrene, chlorostyrenes, vinyl acetate, methyl vinyl ketone, butadiene, isoprene, chloro (or fluoro-)-2-butadiene-1,3; 5-ethyl-2-vinyl-pyridine; 2-vinyl-pyridine; vinyl furane, methacrylonitrile, acrylonitrile methylene malonic esters, vinylidene chloride, vinyl fluoride and fumaric and maleic esters. When hydrolysed or subjected to conditions leading to scission of the ethylene oxide ring the polymers and copolymers are susceptible of cross-linking and consequent insolubilization. In examples: (1) 2,3-epoxypropyl methacrylate prepared from epichlorohydrin and sodium methacrylate (see Group IV (b)) is polymerized in the presence of benzoin by exposure under a nitrogen atmosphere to the light of a Westinghouse H-4 lamp; (2) the same ester is mixed with vinyl chloride and lauroyl peroxide and the mixture heated in a glass container under nitrogen, to yield a copolymer; (3) and (4) 2,3-epoxypropyl methacrylate is copolymerized with methyl-alpha chloroacrylate and acrylonitrile respectively, by heating under nitrogen, a solution of ammonium persulphate and sodium bisulphite being included in the polymerization mixture in (4). A copolymer of the same ester with acrylonitrile may also be prepared by bulk polymerization in the presence of benzoyl peroxide. The Specification as open to inspection under Sect. 91 refers to the polymerization and copolymerization of monoesters obtained by reacting any epoxy alcohol or an ester-forming derivative thereof with the unsaturated acid or an ester forming derivative thereof (see Group IV (b)). This subject-matter does not appear in the Specification as accepted.ALSO:Esters of 2, 3-epoxy propanol are obtained by reacting an epihalohydrin with an alkali metal salt of an acid having the formula R-CH=CR1-COOH wherein R is hydrogen or a monovalent organic radical and R1 is hydrogen, a halogen atom or a monovalent organic radical. The reaction is preferably effected under substantially neutral conditions. Specified acids are acrylic, methacrylic, and alpha-chloroacrylic acids, crotonic, cinnamic and sorbic acids, alpha-phenyl acrylic acid, beta-benzyl acrylic, beta-benzoyl acrylic, beta-acetyl acrylic and beta-furyl acrylic acids, 4-ethyloctadien-2,4-oic acid, hexadieneoic acid; 5,9-dimethyl decatrien-2,4,8-oic acid; D 1,13-cyclohexadienyl-propenoic acid, and butenedioic acids such as maleic and fumaric acids. Specified alkali metal salts are sodium, potassium and ammonium acrylates, methacrylates, fumarates and maleates. The reaction temperature may be from 0 DEG to 100 DEG C., but temperatures below 30 DEG C. are preferred. The esters are usually isolated by fractional distillation which should be effected in the presence of a polymerization inhibitor such as copper chloride, copper acetate, copper resinate, copper propionate, p-phenylene diamine and hydroquinone. A polymerization inhibitor is also preferably included in the initial reaction mixture. Water or aliphatic or aromatic hydrocarbons may be employed as reaction media. In an example, methacrylic acid is added to an aqueous solution of sodium hydroxide and the resulting solution of the sodium salt is cooled and the pH adjusted to 7.0. Cuprous chloride is added and epichlorhydrin is then added dropwise and the mixture stirred at room temperature. It is then extracted with ether and after removing the ether and adding a little cuprous chloride the extract is fractionated under vacuum to yield 2,3-epoxypropyl methacrylate. The esters may be polymerized or copolymerized with other polymerizable compounds (see Group IV (a)). U.S.A. Specification 2,381,880 is referred to. The Specification as open to inspection under Sect. 91 is not restricted to esters of 2,3-epoxypropanol obtained in the above manner but refers to the production of an ester by reacting an epoxy alcohol or an ester forming derivative thereof, under substantially neutral or alkaline conditions, with the unsaturated acid or an ester forming derivative thereof, the following epoxy alcohols being also specified: epoxy oleyl alcohol, epoxy octadecanol, epoxy dodecanol, 5-6-epoxyhexanol-2,3,4-epoxy-2,2,4-trimethyl pentanol-3, beta-hydroxy ethyl ethylene oxide, 3-hydroxy-1,2-oxidocyclohexane, alpha - hydroxymethyl alpha - phenylethylene oxide, and 3,4 - dihydroxybenzyl ethylene oxide. Other specified starting materials are acrylyl chloride, methyl acrylate, ethyl methacrylate, diethyl maleate and diethyl fumarate. The anhydrides, acyl halides, esters, salts and amides of the acids are also specified as starting materials. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US648959XA | 1945-08-17 | 1945-08-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB648959A true GB648959A (en) | 1951-01-17 |
Family
ID=22058928
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB24626/46A Expired GB648959A (en) | 1945-08-17 | 1946-08-19 | Improvements in or relating to the preparation of esters of 2,3-epoxy propanol and to polymerisation products thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB648959A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3073803A (en) * | 1958-11-26 | 1963-01-15 | Henkel & Cie Gmbh | Epoxy alkyl condensates with aromatic hydrocarbon polycarboxylic acids and process of making same |
GB2294044A (en) * | 1994-10-11 | 1996-04-17 | Daicel Chem | Alkenyl and epoxy (meth)acrylates and polymers thereof |
EP1538147A1 (en) * | 2003-12-02 | 2005-06-08 | Mitsubishi Gas Chemical Company, Inc. | Method of producing glycidyl 2-hydroxyisobutyrate |
-
1946
- 1946-08-19 GB GB24626/46A patent/GB648959A/en not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3073803A (en) * | 1958-11-26 | 1963-01-15 | Henkel & Cie Gmbh | Epoxy alkyl condensates with aromatic hydrocarbon polycarboxylic acids and process of making same |
GB2294044A (en) * | 1994-10-11 | 1996-04-17 | Daicel Chem | Alkenyl and epoxy (meth)acrylates and polymers thereof |
GB2294044B (en) * | 1994-10-11 | 1999-02-17 | Daicel Chem | An epoxy (meth)acrylate,a (meth)acrylic resin having epoxy groups, a thermosetting resin composition, a coating composition, a powder coating composition |
EP1538147A1 (en) * | 2003-12-02 | 2005-06-08 | Mitsubishi Gas Chemical Company, Inc. | Method of producing glycidyl 2-hydroxyisobutyrate |
US7074946B2 (en) | 2003-12-02 | 2006-07-11 | Mitsubishi Gas Chemical Co., Ltd. | Method of producing glycidyl 2-hydroxyisobutyrate |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2524432A (en) | Esters of epoxy alcohols with propenoic compounds | |
GB920810A (en) | Preparation of interpolymers of aldehyde-modified acrylamides | |
US3239557A (en) | Process for converting halides to esters | |
FR2569411B1 (en) | NOVEL PROCESS FOR THE MANUFACTURE OF ETHYLENE RADICAL TERPOLYMERS AND ETHYLENE RADICAL COPOLYMERS | |
FR2569412B1 (en) | NOVEL PROCESS FOR THE MANUFACTURE OF ETHYLENE RADICAL TERPOLYMERS AND ETHYLENE RADICAL COPOLYMERS | |
US2359038A (en) | Interpolymerization products of diene synthesis products and compounds having an omega-methylene group and process of their production | |
GB648959A (en) | Improvements in or relating to the preparation of esters of 2,3-epoxy propanol and to polymerisation products thereof | |
US4558152A (en) | Fluoroacrylic compounds | |
GB1091607A (en) | Azo compounds | |
GB889564A (en) | Production of aqueous dispersion of vinylidene chloride copolymers | |
GB757573A (en) | Process for the production of synthetic resins | |
US2337681A (en) | Copolymer | |
GB697604A (en) | Resinous copolymer adhesives and process of making the same | |
GB772663A (en) | Process for stabilising halogen-containing polymers | |
GB1089494A (en) | N,n-bis-acrylamido-acetic compounds, their method of manufacture and their applications | |
GB1015619A (en) | Improvements in or relating to vinylaromatic polymer preparation | |
GB984310A (en) | Halogen-containing acrylic esters and polymers thereof | |
GB664324A (en) | Improvements in interpolymers | |
US3846390A (en) | Process for producing polyvinyl chloride in the presence of alkyl thioglycolate as a chain transfer agent | |
GB1086036A (en) | New polymers built up from ethene and alkenyl esters and process for their preparation | |
GB1266159A (en) | hydroxyl-group containing copolymers | |
WILEY et al. | γ-Radiation-Induced Addition of Aldehydes to Esters of Maleic, Fumaric, and Acetylenedicarboxylic Acids | |
GB836755A (en) | Improvements in and relating to polymers | |
NO147035B (en) | MAGNESIUM OXIDE BASE GLASS SEPARATOR AND USE OF SAME | |
GB591383A (en) | The preparation of alpha-methylene carboxylic acid fluorides |