GB936808A - Improvements in or relating to the production of epoxy alkyl esters - Google Patents
Improvements in or relating to the production of epoxy alkyl estersInfo
- Publication number
- GB936808A GB936808A GB1739060A GB1739060A GB936808A GB 936808 A GB936808 A GB 936808A GB 1739060 A GB1739060 A GB 1739060A GB 1739060 A GB1739060 A GB 1739060A GB 936808 A GB936808 A GB 936808A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- acids
- reacting
- ester
- esters
- 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
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/40—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds, other than from esters thereof
- C08G63/42—Cyclic ethers; Cyclic carbonates; Cyclic sulfites; Cyclic orthoesters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1515—Three-membered rings
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/55—Epoxy resins
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
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)
- Textile Engineering (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Alkyd resins are made by reacting an epoxy alkyl or epoxycycloalkyl ester of an alkane monocarboxylic acid, in which acid the carbon atom to which the carboxylic acid is directly attached, is a tertiary or quaternary carbon atom (for preparation of esters see Group IV(b)), with polybasic carboxylic acids or anhydrides thereof. Suitable acids are dibasic acids from malonic to sebacic, maleic, fumaric, phthalic, isophthalic, terephthalic, tetrahydroand hexahydro-phthalic acids, diglycolic acid and dimerized fatty acids of drying oils. Suitable anhydrides include Diels-Alder adducts of maleic anhydride with dienes such as terpenes and cyclopentadiene. Catalysts such as Lewis bases, hydroxy compounds, amines, acid amides, mercaptans, dialkyl sulphides and sulphoxides may be used, generally in a quantity of 0,1 to 10% by weight based on the reaction mixture. The alkyd resins may be worked up to paints, lacquers and varnishes; pigments, diluents, phenol formaldehyde, urea formaldehyde or melamine resins being added, if desired. In an example, an alkyd resin is made by reacting with glycerol and phthalic acid anhydride the glycidyl ester of an x-alkylalkane monocarboxylic acid whose hydrocarbon chain contains 9 to 11 carbon atoms (said acid having been made by reacting C8 to C10 alkenes with carbon monoxide and water). Specification 844,312 is referred to.ALSO:The invention comprises an epoxyalkyl or epoxycycloalkyl (other than 2:3-epoxycyclopentyl) ester of an alkane monocarboxylic acid, in which acid the carbon atom to which the carboxylic acid group is directly attached, is a tertiary or quaternary carbon atom, in particular an ester of the formula:- <FORM:0936808/IV(a)/1> in which R1 and R2 represent similar or dissimilar alkyl groups and R3, R4, R5, R6 R7 and R8 each represent hydrogen or a hydrocarbon radical, e.g. an alkyl group. The radicals R4, R5, R6, R7 and R8 may also be bound in pairs by divalent hydrocarbon radicals as with R4 and R7 in epoxycyclohexyl esters. Preferred epoxyalkyl esters are those in which the acid has more than 8 carbon atoms and is obtained by reacting carbon monoxide with water and at least one mono-olefine having from 8 to 18 carbon atoms in the molecule. The epoxyalkyl esters may be made by reacting an alkane monocarboxylic acid as defined above, preferably an a -mono-alkylalkane monocarboxylic acid or a ,a -dialkylalkane monocarboxylic acid, with an epoxy halogen alkane, an epoxyhydroxy alkane or a halohydrin. Alkali metal salts or quaternary ammonium salts of the acids may also be used preferably as an aqueous solution, emulsion or suspension. The reaction may take place in the presence of an esterification catalyst, such as a tertiary amine or quaternary ammonium salt. A small amount of alkali may be added. Solvents such as ketones may be used. The temperature is generally between 50 and 180 DEG C. The epoxyalkyl esters may also be made by epoxidising an ester of an a -alkylalkane monocarboxylic acid and an ethylenically unsaturated alcohol or by epoxidising an ethylenically unsaturated alcohol or derivative which is then converted to the desired ester. The epoxidation is preferably effected with a peracid, e.g. peracetic, performic, perpropionic, perbutyric, pervaleric, permonochloro-acetic, pertrifluoroacetic, percrotonic, diperoxalic, perbenzoic, monoperphthalic and percamphonic acid. Aliphatic hydrocarbon halohydrocarbon ether solvents may be used and temperatures are generally in the range -20 DEG to 100 DEG C. A buffer may be used with the stronger acids, e.g. sodium acetate, sodium carbonate, disodium phosphate, an alkali metal salt of an ion exchanger or alumina. The peracid may be formed in situ from a carboxylic acid or anhydride and hydrogen peroxide, or by oxidation of an aldehyde. Hydroperoxides such as t-butylhydroperoxide may also be used to effect epoxidation. The reaction is catalysed by alkaline substances. The epoxidation may also be effected with hydrogen peroxide at pH of 7 to 10, or with a solution of chromic acid anhydride in concentrated acetic acid. Epoxidation may also take place by reaction of the unsaturated compound with a hypohalous acid followed by splitting of hydrogen halide with a base. The epoxyalkyl esters may be purified by washing with a mixture of water and a water miscible polar liquid such as methanol ethanol or an aliphatic ketone, preferably after being dissolved in an aromatic hydrocarbon, such as xylene. The a -alkylalkane monocarboxylic acids are preferably obtained by reacting carbon monoxide and water with olefins having 3 or more carbons per molecule under the influence of acid catalysts such as phosphoric acid, sulphuric acid and complexes of phosphonic acid with boron fluorides. Detailed examples are given. Specification 844,312 is referred to.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL239307 | 1959-05-19 | ||
NL240769 | 1959-06-30 | ||
NL245932 | 1959-11-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB936808A true GB936808A (en) | 1963-09-11 |
Family
ID=27351016
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1739060A Expired GB936808A (en) | 1959-05-19 | 1960-05-17 | Improvements in or relating to the production of epoxy alkyl esters |
Country Status (3)
Country | Link |
---|---|
CH (1) | CH407080A (en) |
DK (1) | DK105865C (en) |
GB (1) | GB936808A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2521479A1 (en) * | 1974-05-17 | 1975-11-20 | Snam Progetti | PROCESS FOR THE PREPARATION OF EPOXIDES FROM ORGANIC ENOLESTERS |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109608931B (en) * | 2018-12-04 | 2021-11-16 | 广东维拓化工股份有限公司 | Environment-friendly coating for green building wall and preparation method thereof |
-
1960
- 1960-05-17 GB GB1739060A patent/GB936808A/en not_active Expired
- 1960-05-17 CH CH563460A patent/CH407080A/en unknown
- 1960-05-19 DK DK608260A patent/DK105865C/en active
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2521479A1 (en) * | 1974-05-17 | 1975-11-20 | Snam Progetti | PROCESS FOR THE PREPARATION OF EPOXIDES FROM ORGANIC ENOLESTERS |
Also Published As
Publication number | Publication date |
---|---|
CH407080A (en) | 1966-02-15 |
DK105865C (en) | 1966-11-21 |
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