GB644287A - Improvements in or relating to the production of crystalline unsaturated alkyd resins and copolymerizable compositions and amorphous resins therefrom - Google Patents
Improvements in or relating to the production of crystalline unsaturated alkyd resins and copolymerizable compositions and amorphous resins therefromInfo
- Publication number
- GB644287A GB644287A GB28531/45A GB2853145A GB644287A GB 644287 A GB644287 A GB 644287A GB 28531/45 A GB28531/45 A GB 28531/45A GB 2853145 A GB2853145 A GB 2853145A GB 644287 A GB644287 A GB 644287A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- fumaric
- mol
- per cent
- 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
- 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
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/06—Unsaturated polyesters
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Paints Or Removers (AREA)
Abstract
A crystalline unsaturated alkyd resin is formed by reacting fumaric acid with a glycol of general formula HO(CH2)xOH (where x=2 to 18) or a dialkyl derivative thereof in which both alkyl groups are attached to the same carbon atom until the product has an acid number below 100. Glycols mentioned are ethylene, neopentyl, trimethylene, tetramethylene, pentamethylene and hexamethylene glycol, decanediol, 1.10; and octadecane diol 1.18, or mixtures thereof. The reaction mixture may include up to 75 mol. per cent (based on total carboxylic groups) of a symmetrical saturated dicarboxylic acid, e.g. succinic, glutaric, pimerlic, azelaic, terephthalic or sebacic acid, up to 10 mol. per cent of an unsymmetrical dicarboxylic acid, e.g. phthalic or indo-methylene-tetrahydrophthalic, up to 20 mol. per cent of monocarboxylic acid having at least 12 carbon atoms, e.g. lauric or stearic acid, up to 10 mol. per cent of monohydroxy monocarboxylic acid, e.g. o -hydroxycaproic, o -hydroxypelargonic, or o -hydroxydecanoic acid, or up to 10 mol. per cent (based on the total hydroxyl groups) of a monohydric alcohol, e.g. n-butanol, amyl alcohol, cyclohexanol, n-hexanol, 2-methyl hexanol, n-octanol, decanol, dodecanol, tetradecanol, cetyl alcohol, octadecanol, reduced geraniol, benzyl alcohol, phenylethyl alcohol, furfuryl alcohols, tetrahydrofurfuryl alcohol, hydroabietyl alcohol or reduced fatty oil acids. The total proportion of modifiers (other than symmetrical dicarboxylic acids) should not exceed 20 mol. per cent of total hydroxy groups and 20 mol. per cent of total carboxyl groups. Preferably the number of hydroxyl groups in the reaction mixture is equivalent to the number of carboxyl groups. Polymerization catalysts and oxygen are preferably excluded, e.g. by distillation of the reactants in the reaction chamber in absence of air. Inert gas may be introduced into the reaction vessel, e.g. by bubbling through the reactants. Reaction temperature is preferably 150-200 DEG C. or lower if reaction is azeotropic, in which case an esterification catalyst is employed. Examples describe the preparation of unsaturated alkyds from (1) and (2) ethylene glycol and fumaric acid; (3), (4) and (5) ethylene glycol, fumaric and sebacic acid; (6) ethylene glycol, fumaric and stearic acid; (7) neopentyl glycol and fumaric acid; (8) ethylene glycol, fumaric acid and o -hydroxy-decanoic acid. Crystallisation of the resin may be aided by addition of a small proportion of aromatic hydrocarbon. The products may be polymerized by heat or light with the aid of organic peroxides or may be copolymerized with a substance having a CH2=C< group, no conjugated carbon-to-carbon double bonds and a boiling point of at least 60 DEG C. In examples, unsaturated alkyds are copolymerized with (9) to (13) styrene and lauric peroxide; (14) p-methyl styrene and lauric peroxide; (15), (16) diallyl phthalate and benzoyl peroxide; (17), (18) diallyl ammelide and benzoyl peroxide; (19) diallyl phthalate which had been partially polymerized by heating in xylene. These examples include description of the preparation of laminated glass cloth with the compositions, the inclusion of fillers, e.g. wood flour or glass flock, in the compositions to yield moulding powders, the inclusion of p-tertiary butyl catechol in the compositions and the preparation of films from the compositions. The composition may also be used for caulking and sealing seams. Other compounds mentioned as suitable for copolymerizing with the unsaturated alkyd resins are vinyl acetate, acrylonitrile, methacrylonitrile, maleic nitrile, fumaric nitrile, esters of acrylic and methacrylic acids, acrylamide, methacrylamide, p-methyoxystyrene, p-ethoxystyrene, p - cyanostyrene, mono - halogeno - styrenes, iso - propenyl toluenes, dimethyl styrenes, isopropenyl benzene, vinyl naphthalene, vinyl mesitylene, vinyl diphenyls, vinyl carbazole, vinyl phenols, vinyl furane, dialkyl esters of maleic, fumaric or itaconic acid, and a very large number of compounds containing one or more allyl groups. The Specification as open to inspection under Sect. 91 is not limited to the use of fumaric acid, but covers any symmetrical a ,b -unsaturated dicarboxylic acid with transconfiguration, e.g. trans 1,2-dimethyl ethylenedioic acid-1,2. It also mentions still more compounds which may be copolymerized with the unsaturated alkyd resin. This subject-matter does not appear in the Specification as accepted. Specification 600,917 is referred to.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US284087XA | 1944-11-22 | 1944-11-22 | |
US41244XA | 1944-12-04 | 1944-12-04 | |
US150945XA | 1945-09-15 | 1945-09-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB644287A true GB644287A (en) | 1950-10-11 |
Family
ID=27357569
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB28531/45A Expired GB644287A (en) | 1944-11-22 | 1945-10-29 | Improvements in or relating to the production of crystalline unsaturated alkyd resins and copolymerizable compositions and amorphous resins therefrom |
Country Status (3)
Country | Link |
---|---|
CH (1) | CH284087A (en) |
FR (1) | FR917213A (en) |
GB (1) | GB644287A (en) |
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1035357B (en) * | 1955-02-11 | 1958-07-31 | American Cyanamid Co | Process for the production of molded, layered and composite bodies |
US2857359A (en) * | 1954-12-29 | 1958-10-21 | American Cyanamid Co | Process for preparing thixotropic polyester resin composition and product obtained thereby |
US2861981A (en) * | 1954-02-05 | 1958-11-25 | Nat Distillers Chem Corp | Polyesters and isocyanate reaction products thereof |
US2861910A (en) * | 1954-08-31 | 1958-11-25 | Nat Distillers Chem Corp | Polyesters and laminates therefrom |
DE1054620B (en) * | 1956-10-17 | 1959-04-09 | Bayer Ag | Solvent-free, air-drying paints |
DE1056889B (en) * | 1956-03-20 | 1959-05-06 | Huels Chemische Werke Ag | Process for the production of glued socket connections of polyethylene pipes |
DE1058251B (en) * | 1956-07-23 | 1959-05-27 | American Cyanamid Co | Process for the production of molded or laminated bodies and covering materials |
US2921052A (en) * | 1955-08-17 | 1960-01-12 | Eastman Kodak Co | Polyesters of sulfonyldibenzoic acid and gem-dialkyl glycols |
DE1105610B (en) * | 1958-09-26 | 1961-04-27 | Bayer Ag | Process for the production of transparent, corrugated, glass fiber reinforced plastic sheets |
DE1121732B (en) * | 1953-05-11 | 1962-01-11 | Telefunken Patent | Electrolytic capacitor |
US3052591A (en) * | 1957-04-04 | 1962-09-04 | Montedison Spa | Resinous product, method of making same, and use thereof |
US3396128A (en) * | 1962-05-04 | 1968-08-06 | Takeda Chemical Industries Ltd | Method for promoting crystallization of unsaturated polyester resins |
US3419637A (en) * | 1966-06-30 | 1968-12-31 | Ppg Industries Inc | Chemical-resistant polyester resins based upon dicyclohexanols and neopentyl glycol-type diols |
US3959200A (en) * | 1973-10-25 | 1976-05-25 | E. I. Du Pont De Nemours And Company | Copolyester composition |
US3989655A (en) * | 1973-07-09 | 1976-11-02 | Bayer Aktiengesellschaft | Low shrink, free flowing polyester resin systems based on a mixture of a crystalline unsaturated polyester resin, a monomeric copolymerizable component and a cellulose ester |
US4246165A (en) | 1977-12-09 | 1981-01-20 | Nissan Motor Company, Limited | Preparation of coated casting sand using unsaturated polyester resin as binder |
CN109575257A (en) * | 2018-11-16 | 2019-04-05 | 中国科学院宁波材料技术与工程研究所 | Poly- 2,5- furandicarboxylic acid -1,4- neopentyl glycol succinate and preparation method thereof, product |
-
1945
- 1945-10-29 GB GB28531/45A patent/GB644287A/en not_active Expired
- 1945-11-12 FR FR917213D patent/FR917213A/en not_active Expired
- 1945-11-21 CH CH284087D patent/CH284087A/en unknown
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1121732B (en) * | 1953-05-11 | 1962-01-11 | Telefunken Patent | Electrolytic capacitor |
US2861981A (en) * | 1954-02-05 | 1958-11-25 | Nat Distillers Chem Corp | Polyesters and isocyanate reaction products thereof |
US2861910A (en) * | 1954-08-31 | 1958-11-25 | Nat Distillers Chem Corp | Polyesters and laminates therefrom |
US2857359A (en) * | 1954-12-29 | 1958-10-21 | American Cyanamid Co | Process for preparing thixotropic polyester resin composition and product obtained thereby |
DE1035357B (en) * | 1955-02-11 | 1958-07-31 | American Cyanamid Co | Process for the production of molded, layered and composite bodies |
US2921052A (en) * | 1955-08-17 | 1960-01-12 | Eastman Kodak Co | Polyesters of sulfonyldibenzoic acid and gem-dialkyl glycols |
DE1056889B (en) * | 1956-03-20 | 1959-05-06 | Huels Chemische Werke Ag | Process for the production of glued socket connections of polyethylene pipes |
DE1058251B (en) * | 1956-07-23 | 1959-05-27 | American Cyanamid Co | Process for the production of molded or laminated bodies and covering materials |
DE1054620B (en) * | 1956-10-17 | 1959-04-09 | Bayer Ag | Solvent-free, air-drying paints |
US3052591A (en) * | 1957-04-04 | 1962-09-04 | Montedison Spa | Resinous product, method of making same, and use thereof |
DE1105610B (en) * | 1958-09-26 | 1961-04-27 | Bayer Ag | Process for the production of transparent, corrugated, glass fiber reinforced plastic sheets |
US3396128A (en) * | 1962-05-04 | 1968-08-06 | Takeda Chemical Industries Ltd | Method for promoting crystallization of unsaturated polyester resins |
US3419637A (en) * | 1966-06-30 | 1968-12-31 | Ppg Industries Inc | Chemical-resistant polyester resins based upon dicyclohexanols and neopentyl glycol-type diols |
US3989655A (en) * | 1973-07-09 | 1976-11-02 | Bayer Aktiengesellschaft | Low shrink, free flowing polyester resin systems based on a mixture of a crystalline unsaturated polyester resin, a monomeric copolymerizable component and a cellulose ester |
US3959200A (en) * | 1973-10-25 | 1976-05-25 | E. I. Du Pont De Nemours And Company | Copolyester composition |
US4246165A (en) | 1977-12-09 | 1981-01-20 | Nissan Motor Company, Limited | Preparation of coated casting sand using unsaturated polyester resin as binder |
CN109575257A (en) * | 2018-11-16 | 2019-04-05 | 中国科学院宁波材料技术与工程研究所 | Poly- 2,5- furandicarboxylic acid -1,4- neopentyl glycol succinate and preparation method thereof, product |
CN109575257B (en) * | 2018-11-16 | 2021-09-07 | 中国科学院宁波材料技术与工程研究所 | Poly (2, 5-furandicarboxylic acid-1, 4-butanedioic acid neopentyl glycol ester), and preparation method and product thereof |
Also Published As
Publication number | Publication date |
---|---|
FR917213A (en) | 1946-12-30 |
CH284087A (en) | 1952-07-15 |
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