CH200377A - Process for the preparation of a resinous condensation product. - Google Patents
Process for the preparation of a resinous condensation product.Info
- Publication number
- CH200377A CH200377A CH200377DA CH200377A CH 200377 A CH200377 A CH 200377A CH 200377D A CH200377D A CH 200377DA CH 200377 A CH200377 A CH 200377A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- condensation product
- preparation
- glycerol
- resinous condensation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 239000007859 condensation product Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 23
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 17
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000004310 lactic acid Substances 0.000 claims description 3
- 235000014655 lactic acid Nutrition 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 claims description 2
- 239000011810 insulating material Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 150000007519 polyprotic acids Polymers 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- VIWIWXKTPWZMEW-UHFFFAOYSA-N 2-hydroxypropanoic acid;propane-1,2,3-triol Chemical compound CC(O)C(O)=O.OCC(O)CO VIWIWXKTPWZMEW-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004870 electrical engineering Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 230000009975 flexible effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012262 resinous product Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Polyesters Or Polycarbonates (AREA)
- Organic Insulating Materials (AREA)
Description
Verfahren zur Herstellung eines harzartigen Kondensationsproduktes. Es ist bekannt, durch Kondensation von mehrwertigem Alkohol, insbesondere Glycerin und mehrbasischen Säuren, insbesondere Phtalsäure, ein harzartiges Produkt herzu stellen, das im Laufe der Entwicklung durch zusätzliche weitere Bestandteile in seinen Eigenschaften beeinflusst worden ist. Es hatte sich gezeigt, dass das aus Glycerin und Phtal- säure bestehende Harz technisch schlecht ver wertbar war und die Verwertbarkeit erst durch Zusätze gehoben wurde. Man hat die aromatische Dicarbonsäure (Phtalsäure) teil weise durch andere mehr- und einbasische aliphatische Säuren, wie z. B.
Bernsteinsäure, Buttersäure, Zitronensäure und dergl. ersetzt, um auf diese Weise die Plastizität des Harzes zu erhöhen. Auch trocknende Öle bezw. Öl säure sind mit dem Alkohol und der mehr basischen Säure zur Umsetzung gebracht wor den, ebenfalls um die Eigenschaften des Har zes zu verbessern. Ein neuer Vorschlag gebt dahin, mehrere gtimponenten, wie z. B. Phtalsäure, Bernstein säure, Adipinsäure, Glycerin, Glykol, trock nendes Öl und dergl. durch chemische Reak tion bei geeigneten Temperaturen zu vereinigen und ein Harz mit hohen biegsamen Eigen schaften zu erzielen.
Es wurde nun gefunden, dass man ein besonders zähes, insbesondere zur Lackherstellung geeignetes Harz aus mehr wertigem Alkohol und mehrbasischer Säure erhalten kann, wenn man die Kondensation mit Oxykarbonsäure durchführt.
Die Erfindung betrifft ein Verfahren zur Herstellung eines harzartigen Kondensations produktes, unter Verwendung von Glycerin und Phtalsäure, welches sich dadurch aus zeichnet, dass man das Glycerin zunächst mit Milchsäure verestert und dann den entstehen den Ester mit Phtalsäure kondensiert.
Die Kondensation wird zweckmässig bei Temperaturen durchgeführt, die an sich bei der Glyptalbarzherstellung bekannt sind. Ausführungsbeispiel: 92 g Glycerin (s=1,26) werden mit 300 g 90 o%iger Milchsäure in einem indifferenten Gasstrom auf ca. 195 bis zur vollständigen Austreibung des Reaktionswassers der ein setzenden Esterreaktion erhitzt.
Das ent stehende milchsaure Glycerin ist eine schwach gelblich gefärbte, hochviskose Flüssigkeit, die mit 222 g Phtalsäureanhydrid bei ca. 222 0 durch Substitution der OH-Gruppen der Milch säurereste durch Phtalsäurereste bis auf 90 bis 92 % der Theorie weiter verestert wird. Das nach dem Erkalten ausfallende Konden sationsprodukt stellt ein gelbes Harz dar, welches in Aceton und in einem Gemisch von Alkohol und Benzol leicht löslich ist, und das bei 140-200 o C zu einer elastischen, hornartigen Masse härtet. Es soll als elektri sches Isoliermaterial, insbesondere aber zur Herstellung von Lacken verwendet werden.
Die besonders grosse Zähigkeit, die dem Verfahrensprodukt eignet, ist offenbar mit der durch die stufenweise Veresterung er reichten Molekülvergrösserung zu erklären. Das Verfahrensprodukt lässt sich in der von Glyptalharzen allgemein bekannten Weise weiter verarbeiten und ist demzufolge härtbar und besitzt ferner in elektrischer Hinsicht Eigenschaften, die seine Anwendung auch auf elektrotechnischem Gebiete in weitem Um fange sichert.
Process for the preparation of a resinous condensation product. It is known that by condensation of polyhydric alcohol, in particular glycerol and polybasic acids, in particular phthalic acid, a resinous product can be produced, the properties of which have been influenced in the course of development by additional components. It had been shown that the resin, consisting of glycerine and phthalic acid, was technically difficult to use and that the usability was only increased by additives. You have the aromatic dicarboxylic acid (phthalic acid) partly by other poly- and monobasic aliphatic acids, such as. B.
Succinic acid, butyric acid, citric acid and the like. Replaced in order to increase the plasticity of the resin in this way. Also drying oils respectively. Oleic acid are reacted with the alcohol and the more basic acid, also to improve the properties of the resin. A new suggestion is that several gtimponenten, such as B. phthalic acid, succinic acid, adipic acid, glycerol, glycol, drying oil and the like. To unite through chemical reac tion at suitable temperatures and to achieve a resin with high flexible properties.
It has now been found that a particularly tough resin, particularly suitable for paint production, can be obtained from polyhydric alcohol and polybasic acid if the condensation is carried out with oxycarboxylic acid.
The invention relates to a method for producing a resinous condensation product, using glycerol and phthalic acid, which is characterized in that the glycerol is first esterified with lactic acid and then the resulting ester is condensed with phthalic acid.
The condensation is expediently carried out at temperatures which are known per se in the production of glyptal ore. Exemplary embodiment: 92 g of glycerol (s = 1.26) are heated with 300 g of 90% strength lactic acid in an inert gas stream to approx. 195 until the water of reaction is completely expelled by the ester reaction that is starting.
The resulting lactic acid glycerine is a slightly yellowish, highly viscous liquid which is further esterified with 222 g of phthalic anhydride at approx. 222 ° by substituting phthalic acid residues for the OH groups of the lactic acid residues up to 90 to 92% of theory. The condensation product that precipitates after cooling is a yellow resin which is easily soluble in acetone and in a mixture of alcohol and benzene and which hardens at 140-200 o C to an elastic, horn-like mass. It should be used as an electrical insulating material, but especially for the production of paints.
The particularly high toughness which is suitable for the process product can evidently be explained by the enlargement of the molecule achieved through the gradual esterification. The process product can be further processed in the manner generally known from glyptal resins and is consequently curable and also has electrical properties that ensure its application in the electrical engineering field to a large extent.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE200377X | 1935-08-10 | ||
| CH200377T | 1936-08-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH200377A true CH200377A (en) | 1938-10-15 |
Family
ID=25723503
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH200377D CH200377A (en) | 1935-08-10 | 1936-08-05 | Process for the preparation of a resinous condensation product. |
| CH210744D CH210744A (en) | 1935-08-10 | 1938-02-23 | Process for the production of an alkyd resin. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH210744D CH210744A (en) | 1935-08-10 | 1938-02-23 | Process for the production of an alkyd resin. |
Country Status (1)
| Country | Link |
|---|---|
| CH (2) | CH200377A (en) |
-
1936
- 1936-08-05 CH CH200377D patent/CH200377A/en unknown
-
1938
- 1938-02-23 CH CH210744D patent/CH210744A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH210744A (en) | 1940-07-31 |
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