GB788123A - Epoxy derivatives and process of preparing the same - Google Patents
Epoxy derivatives and process of preparing the sameInfo
- Publication number
- GB788123A GB788123A GB23384/55A GB2338455A GB788123A GB 788123 A GB788123 A GB 788123A GB 23384/55 A GB23384/55 A GB 23384/55A GB 2338455 A GB2338455 A GB 2338455A GB 788123 A GB788123 A GB 788123A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxatricyclo
- octane
- imide
- dicarboximide
- heptene
- 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
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/08—Bridged systems
-
- 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
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
Abstract
The invention comprises epoxides of the formula <FORM:0788123/IV (b)/1> wherein X1 and X2 represent cyano, carboxyl, carboalkoxy, carboaryloxy, carboalkoxyalkoxy or amido radicals, or taken together represent a dicarboxylic anhydride, imide or N-substituted imide grouping, the N-substituent being preferably an alkyl or alkoxyalkyl radical. The compounds are prepared by reacting the corresponding 3 : 6-methylene-1 : 2 : 3 : 6-tetrahydrophthalic acid, -ester, -anhydride, -cyanide, -amide, -imide or -N-substituted imide with peracetic acid in the presence of an inert organic volatile solvent. Specified solvents are acetone, acetal, methylethyl ketone and butyl acetate. The epoxidation is preferably carried out at a temperature of 30 DEG to 120 DEG C. Specified starting materials are endo- and exo-3 : 6-methylene - 1 : 2 : 3 : 6 - tetrahydrophthalic anhydrides, diethyl (exo and endo)-3 : 6-methylene - 1 : 2 : 3 : 6 - tetrahydrophthalates, bicyclo - [2,2,1] - 5 - heptene - 2 : 3 - dicarboximide, and N-methyl-, N-ethyl-, N-propyl-, N - isopropyl-, N - (b - hydroxyethyl)-, N-allyl-, N-butyl-, N-amyl-, N-(2-ethylhexyl)-, N-(n-heptyl)-, N-(n-octyl)-, N-(hexoxypropyl)-, N-(hexoxyethoxypropyl)-, N - (2 - ethylhexoxypropyl)-, N - (2 - ethylbutoxyethoxypropyl)-, and N - (4 : 7 - dioxanonyl) - bicyclo - [2,2,1]-5-heptene-2 : 3-dicarboximides. The examples describe the preparation of 3 - oxatricyclo[3,2,1,02 : 4] - octane - 6 : 7 - dicarboxylic acid anhydride, N - (hexoxyethoxypropyl) - 3 - oxatricyclo - [3,2,1,02 : 4] - octane - 6 : 7 - dicarboximide and diethyl 3-oxatricyclo-[3,2,1,02 : 4]-octane-6 : 7-dicarboxylate. N-Alkyl- and N-alkoxyalkyl-bicyclo-[2,2,1]-5-heptene-2 : 3-dicarboximide starting materials are prepared by reacting bicyclo-[2,2,1]-5-heptene-2 : 3-dicarboxylic anhydride with an appropriate alkylamine or alkoxyalkylamine. 3-(2-Hexoxyethoxy)-propylamine is prepared by catalytic hydrogenation of 3-(2-hexoxyethoxy)-propionitrile. 3-(2-Hexoxyethoxy)-propionitrile is prepared by reacting 2-hexoxyethanol with acrylonitrile.ALSO:Vinyl chloride resins are stabilized or plasticized and phenol-aldehyde resins are modified with epoxides of the formula: <FORM:0788123/IV (a)/1> wherein X1 and X2 represent cyano, carboxyl, carboalkoxy, carboaryloxy, carboalkoxyalkoxy or amido radicals, or taken together represent a dicarboxylic anhydride, imide or N-substituted imide grouping, the N-substituent being preferably an alkyl or alkoxyalkyl radical. Exemplified epoxides are 3 - oxatricyclo - [3.2.1.02 : 4]-octane - 6 : 7 - dicarboxylic anhydride, N-(hexoxyethoxypropyl) - 3 - oxatricyclo - [3.2.1. 02 : 4] - octane - 6 : 7 - dicarboximide and diethyl 3 - oxatricyclo - [3.2.1.02 : 4] - octane - 6 : 7-dicarboxylate.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US788123XA | 1954-09-08 | 1954-09-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB788123A true GB788123A (en) | 1957-12-23 |
Family
ID=22146360
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB23384/55A Expired GB788123A (en) | 1954-09-08 | 1955-08-15 | Epoxy derivatives and process of preparing the same |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB788123A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3238227A (en) * | 1960-05-31 | 1966-03-01 | Union Carbide Corp | Epoxy derivatives and process of preparing the same |
US3455949A (en) * | 1965-03-23 | 1969-07-15 | Ciba Ltd | Hexahydrophthalimide polyepoxide compounds |
US5268489A (en) * | 1991-06-26 | 1993-12-07 | Union Carbide Chemicals & Plastics Technology Corporation | Production of unsaturated cycloaliphatic esters and derivatives thereof |
US20140066590A1 (en) * | 2011-04-28 | 2014-03-06 | Nissan Chemical Industries, Ltd. | Polyimide precursor modified with dicarboxylic acid anhydride, imidized polyimide and liquid crystal aligning agent using it |
-
1955
- 1955-08-15 GB GB23384/55A patent/GB788123A/en not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3238227A (en) * | 1960-05-31 | 1966-03-01 | Union Carbide Corp | Epoxy derivatives and process of preparing the same |
US3455949A (en) * | 1965-03-23 | 1969-07-15 | Ciba Ltd | Hexahydrophthalimide polyepoxide compounds |
US5268489A (en) * | 1991-06-26 | 1993-12-07 | Union Carbide Chemicals & Plastics Technology Corporation | Production of unsaturated cycloaliphatic esters and derivatives thereof |
US20140066590A1 (en) * | 2011-04-28 | 2014-03-06 | Nissan Chemical Industries, Ltd. | Polyimide precursor modified with dicarboxylic acid anhydride, imidized polyimide and liquid crystal aligning agent using it |
US9447240B2 (en) * | 2011-04-28 | 2016-09-20 | Nissan Chemical Industries, Ltd. | Polyimide precursor modified with dicarboxylic acid anhydride, imidized polyimide and liquid crystal aligning agent using it |
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