GB937412A - Esters containing epoxide groups, their production and their use - Google Patents
Esters containing epoxide groups, their production and their useInfo
- Publication number
- GB937412A GB937412A GB3917059A GB3917059A GB937412A GB 937412 A GB937412 A GB 937412A GB 3917059 A GB3917059 A GB 3917059A GB 3917059 A GB3917059 A GB 3917059A GB 937412 A GB937412 A GB 937412A
- Authority
- GB
- United Kingdom
- Prior art keywords
- epoxy
- endomethylene
- group
- cyclohexyl
- compounds
- 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
-
- 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
- C07D303/40—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 by ester radicals
- C07D303/44—Esterified with oxirane-containing hydroxy 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
- C08G59/18—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
Abstract
Compounds of the formula <FORM:0937412/IV(a)/1> where n is 1 or 2, and Z is the residue of a carboxylic acid having n carboxyl groups, the said residue containing an epoxide group when n is 1 and optionally containing an epoxide group when n is 2 (see Group IV(b)) may be cross-linked or hardened by conventional hardeners for epoxide compounds. The hardeners may be acidic or basic, many being specified. The preferred hardeners are polybasic carboxylic acids and their anhydrides. Accelerators may also be present, such as tertiary amines or polyhydroxy compounds. Hardenable compositions comprise one or more esters of the above general formula together with one or more hardening agents and preferably also a proportion of an ester of the above general formula in which some or all of the epoxide groups are hydrolysed to hydroxyl groups, and/or contain other polyhydroxy compounds. Other epoxides may also be present in the compositions, as may fillers, plasticizers or colouring agents. In Example 3, a resin is formed by curing 3,4-epoxy-2,5-endomethylene-cyclohexyl-3, 4-epoxy- D 3-tetrahydrobenzoate with phthalic anhydride and benzyldimethylamine; the epoxidized ester may be stored in the form of an adduct with phthalic anhydride and subsequently cured by heating.ALSO:The invention comprises compounds of the formula <FORM:0937412/IV(a)/1> where n is 1 or 2, and Z is the residue of a carboxylic acid having n carboxyl groups, the said residue containing an epoxide group when n is 1 and optionally an epoxide group when n is 2. Preferred compounds are those of the general formula <FORM:0937412/IV(a)/2> wherein R1 and R2 are separately hydrogen or together represent an endomethylene group, and R3 represents a hydrogen atom or a methyl group, and those of the general formula <FORM:0937412/IV(a)/3> wherein A represents a divalent aliphatic, cycloaliphatic or aromatic residue which may be substituted by a hydroxyl group. The compounds are prepared by epoxidising a compound of formula <FORM:0937412/IV(a)/4> wherein n is 1 or 2, and Z1 stands for the residue of a carboxylic acid having n carboxyl groups, said residue containing an epoxidisable group when n is 1, and optionally containing an epoxidisable group when n is 2, the term "epoxidisable group" being defined in the Specification. The epoxidation may be carried out by treatment with per-acids and the reaction product may contain compounds in which some or all of the epoxide groups have been hydrolysed to hydroxyl groups. The esters which are to be epoxidised are prepared by esterification of dehydronoborneol with the corresponding acids or their anhydrides or acid chlorides, numerous acids, including halogen substituted acids, being specified. In Example (1) dehydroporborneol is esterified with succinic anhydride in the presence of xylene and toluene-p-sulphonic acid, and the product treated with peracetic acid to give bis-3,4-epoxy-2,5-endomethylene-cyclohexyl succinate. In further examples using a similar method dehydronorborneol gives: (2) bis-3,4-epoxy-2,5-endomethylene-cyclohexyl phthalate from phthalic anhydride; (3) 3,4-epoxy-2,5-endomethylene-cyclohexyl 3,4-epoxy-D 3-tetrahydrobenzoate from 1,2,5,6-tetrahydro-benzoic acid: (4) bis-3,4-epoxy- 2,5-endomethylenecyclohexyl 4,5-epoxy-D 4-tetrahydrophthalate from 1,2,3,6-tetrahydro-phthalic anhydride; (5) 3,4-epoxy-2,5-endomethylene-cyclohexyl 3,4-epoxy-2,5-endomethylene-D 3-tetrahydrobenzoate from 2,5-endomethylene- 1,2,5,6-tetrahydro-benzoic acid; (6) 3,4-epoxy-2,5-endomethylene-cyclohexyl 9,10-epoxy-octadecanoate from oleic acid; (7) 3,4-epoxy-2,5-endomethylene-cyclohexyl 6-methyl-3,4-epoxy-2,5-endomethylene-D 3-tetrahydrobenzoate from 6-methyl-2,5-endomethylene- D 3-tetrahydrobenzoic acid. The Provisional Specification refers to epoxidised esters derived from alcohols other than dehydronorborneol in which the hydrogen atoms of dehydronorborneol may be replaced by monovalent substituents such as halogen atoms, alkoxy groups and aliphatic, cycloaliphatic, araliphatic or aromatic hydrocarbon residues, and the endomethylene group may be any divalent group, and to mixed esters of the polybasic acids with more than one of such alcohols. The products may be treated with acidic or basic hardeners to give resins (see Group IV(a)). The epoxidised ester prepared in Example 3 forms an adduct with phthalic anhydride.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3917059A GB937412A (en) | 1959-11-18 | 1959-11-18 | Esters containing epoxide groups, their production and their use |
BE597224A BE597224A (en) | 1959-11-18 | 1960-11-18 | Esters containing epoxy groups, and processes for their preparation and applications of these esters |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3917059A GB937412A (en) | 1959-11-18 | 1959-11-18 | Esters containing epoxide groups, their production and their use |
Publications (1)
Publication Number | Publication Date |
---|---|
GB937412A true GB937412A (en) | 1963-09-18 |
Family
ID=10408056
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3917059A Expired GB937412A (en) | 1959-11-18 | 1959-11-18 | Esters containing epoxide groups, their production and their use |
Country Status (2)
Country | Link |
---|---|
BE (1) | BE597224A (en) |
GB (1) | GB937412A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001181269A (en) * | 1999-12-27 | 2001-07-03 | Asahi Kasei Corp | Method for producing new alicyclic epoxy compound |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB996745A (en) * | 1962-06-28 | 1965-06-30 | Hitachi Chemical Co Ltd | Self-copolymerizable resinous compositions |
-
1959
- 1959-11-18 GB GB3917059A patent/GB937412A/en not_active Expired
-
1960
- 1960-11-18 BE BE597224A patent/BE597224A/en unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001181269A (en) * | 1999-12-27 | 2001-07-03 | Asahi Kasei Corp | Method for producing new alicyclic epoxy compound |
JP4553432B2 (en) * | 1999-12-27 | 2010-09-29 | 旭化成イーマテリアルズ株式会社 | Method for producing novel alicyclic epoxy compound |
Also Published As
Publication number | Publication date |
---|---|
BE597224A (en) | 1961-05-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ES407331A1 (en) | Low-cost resinous compositions comprising non-glycidyl ether epoxides | |
US4474941A (en) | Alkyd resins containing functional epoxides | |
US2993920A (en) | Resins and method of making the same | |
GB852409A (en) | Improvements in and relating to curing epoxy resins | |
GB1255504A (en) | New long-chain polyglycidyl esters containing aromatic acid residues, processes for their manufacture and their use | |
GB1005241A (en) | Thio-derivatives of polyacid anhydrides and resinous compositions derived therefrom | |
GB937412A (en) | Esters containing epoxide groups, their production and their use | |
US2967840A (en) | Polyesters of 4, 5-epoxycyclohexane-1, 2-dicarboxylic acids | |
GB977958A (en) | A process for the preparation of partially esterified amino alcohols | |
US3436377A (en) | Polymers with high heat distortion temperatures prepared from epoxypolybutadiene hardened with polyols and anhydrides | |
GB934407A (en) | Resinous condensation products of mono-epoxy compounds and aromatic carboxylic anhydrides | |
US3560411A (en) | Epoxyalkyl esters of endo-methylene hexahydrophthalic acid | |
US2967837A (en) | Compositions and methods for curing epoxy resins | |
ES368472A1 (en) | Adducts containing epoxide groups from polyepoxide compounds and acid polyesters of aliphatic cycloaliphatic dicarboxylic acids | |
GB987927A (en) | Improvements in or relating to the curing of epoxides | |
GB1111038A (en) | Stable liquid dicarboxylic acid anhydride compositions | |
US3223657A (en) | Resinous composition comprising an epoxidized ester of a neopentyl polyhydric alcohol | |
GB799714A (en) | Improvements in epoxide resin compositions and the like | |
GB996064A (en) | Improvements in and relating to epoxy resins | |
US3558535A (en) | Coating compositions comprising an epoxidized fatty ester of a cyclic polyol and an acidic polyester | |
US3468704A (en) | Carboxyl-terminated polyesters and coating composition derived therefrom | |
GB907149A (en) | Esters containing epoxide groups, their production and their uses | |
US3050478A (en) | Solidifiable fluid compositions prepared from enedioyl acids, epoxidized hydrocarbondrying oil, and conjugated dienes | |
US3699064A (en) | Carboxylic curing agent | |
GB1101380A (en) | Epoxy resin compositions |