GB907149A - Esters containing epoxide groups, their production and their uses - Google Patents
Esters containing epoxide groups, their production and their usesInfo
- Publication number
- GB907149A GB907149A GB3757559A GB3757559A GB907149A GB 907149 A GB907149 A GB 907149A GB 3757559 A GB3757559 A GB 3757559A GB 3757559 A GB3757559 A GB 3757559A GB 907149 A GB907149 A GB 907149A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- aromatic
- groups
- group
- epoxide
- 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
- 150000002148 esters Chemical class 0.000 title abstract 6
- 125000003700 epoxy group Chemical group 0.000 title 1
- 150000002118 epoxides Chemical group 0.000 abstract 8
- 125000003118 aryl group Chemical group 0.000 abstract 6
- 239000004593 Epoxy Substances 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- 239000003795 chemical substances by application Substances 0.000 abstract 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 3
- -1 aromatic monocarboxylic acid Chemical class 0.000 abstract 3
- 238000006735 epoxidation reaction Methods 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 150000003944 halohydrins Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 229920005989 resin Polymers 0.000 abstract 2
- 239000011347 resin Substances 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 abstract 1
- UWRZIZXBOLBCON-UHFFFAOYSA-N 2-phenylethenamine Chemical compound NC=CC1=CC=CC=C1 UWRZIZXBOLBCON-UHFFFAOYSA-N 0.000 abstract 1
- WDDOGQUMKOBLOG-UHFFFAOYSA-N 4-(7-oxabicyclo[4.1.0]heptan-3-yloxy)-4-oxobutanoic acid Chemical compound C1CC2C(O2)CC1OC(=O)CCC(=O)O WDDOGQUMKOBLOG-UHFFFAOYSA-N 0.000 abstract 1
- 239000004150 EU approved colour Substances 0.000 abstract 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 abstract 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical class OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- 239000003822 epoxy resin Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 150000002540 isothiocyanates Chemical class 0.000 abstract 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 abstract 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 abstract 1
- 150000004967 organic peroxy acids Chemical class 0.000 abstract 1
- 150000004707 phenolate Chemical class 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 229920000647 polyepoxide Polymers 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- C07D303/16—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Epoxy Compounds (AREA)
Abstract
A hardenable composition comprises one or more epoxy esters containing two epoxide groups and having the general formula <FORM:0907149/IV(a)/1> wherein R1, R2, R3, R4, R5, R6, R7, R8 and R9 represent hydrogen atoms or monovalent substituents, e.g. halogen atoms, alkoxy groups, or hydrocarbon residues, n represents 1 or 2 and Z represents the residue of a non-aromatic monocarboxylic acid which contains an epoxide group or a non-aromatic dicarboxylic acid free from epoxide groups, wherein the term non-aromatic excludes only those acids in which a carboxylic group is attached directly to an aromatic nucleus, together with one or more hardening agents for epoxy resins, preferably polycarboxylic acids and their anhydrides. Other hardening agents specified include amines, amides, anilineformaldehyde resins, aminostyrene polymers, isocyanates, isothiocyanates, polyhydric phenols, phenol-aldehyde resins, products of aluminium alkoxides or phenolates with tautomeric compounds, FriedelCrafts catalysts and phosphoric acid. The hardenable mixtures may also contain a proportion of said epoxy ester in which the epoxide groups are complete or partially hydrolysed to hydroxyl groups, and/or other polyhydroxy compounds or other epoxides. The compositions may contain fillers, plasticizers or colouring agents.ALSO:The invention comprises epoxy esters containing two epoxide groups having the formula: <FORM:0907149/IV (b)/1> wherein R1, R2, R3, R4, R5, R6, R7, R8 and R9 represent hydrogen atoms or monovalent substituents such as halogen atoms, alkoxy groups or aliphatic, cycloaliphatic, araliphatic or aromatic hydrocarbon residues, n represents 1 or 2 and Z represents the residue of a non-aromate monocarboxylic acid which contains an epoxide group or stands for the residue of a non-aromatic dicarboxylic acid free from epoxide groups, wherein the term non-aromatic excludes only those acids in which a carboxylic group is attached directly to an aromatic nucleus. The novel esters are made by epoxidation of the corresponding esters containing a carbon-carbon double bond in the ring and, when n is 1, an epoxidisable group in Z, i.e. a double bond or a halohydrin group. The starting materials are made by esterifying D 3-cyclohexanols using the carboxylic acid, anhydride or acid halide, if necessary in the presence of an esterification catalyst, e.g. toluene-p-sulphonic acid. The epoxidation of the double bonds may be effected by treatment with organic peracids, e.g. peracetic, perbenzoic, peradipic or monoperphthalic acid, or by treatment with hypochlorous acid followed by an HCl-eliminating agent, e.g. a strong alkali. The epoxidation of halohydrin groups in Z may be effected with a dehydrohalogenating agent such as potassium hydroxide or sodium hydroxide. Examples describe the preparation of bis-3 : 4-epoxycyclohexyl succinate and 3 : 4-epoxycyclohexyl-3 : 4 - epoxy - tetrahydrobenzoate.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3757559A GB907149A (en) | 1959-11-05 | 1959-11-05 | Esters containing epoxide groups, their production and their uses |
| BE595390A BE595390A (en) | 1959-11-05 | 1960-09-23 | Esters containing epoxy groups, their preparation and uses. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3757559A GB907149A (en) | 1959-11-05 | 1959-11-05 | Esters containing epoxide groups, their production and their uses |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB907149A true GB907149A (en) | 1962-10-03 |
Family
ID=10397480
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3757559A Expired GB907149A (en) | 1959-11-05 | 1959-11-05 | Esters containing epoxide groups, their production and their uses |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE595390A (en) |
| GB (1) | GB907149A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5767150A (en) * | 1997-04-10 | 1998-06-16 | Sartomer Company | Cycloaliphatic epoxide compounds |
-
1959
- 1959-11-05 GB GB3757559A patent/GB907149A/en not_active Expired
-
1960
- 1960-09-23 BE BE595390A patent/BE595390A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5767150A (en) * | 1997-04-10 | 1998-06-16 | Sartomer Company | Cycloaliphatic epoxide compounds |
| US6084111A (en) * | 1997-04-10 | 2000-07-04 | Sartomer Technologies Inc. | Method for making cycloaliphatic epoxides |
Also Published As
| Publication number | Publication date |
|---|---|
| BE595390A (en) | 1961-08-23 |
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