DE534784C - Process for the production of soluble, resinous condensation products from phenols and formaldehyde - Google Patents
Process for the production of soluble, resinous condensation products from phenols and formaldehydeInfo
- Publication number
- DE534784C DE534784C DEB126206D DEB0126206D DE534784C DE 534784 C DE534784 C DE 534784C DE B126206 D DEB126206 D DE B126206D DE B0126206 D DEB0126206 D DE B0126206D DE 534784 C DE534784 C DE 534784C
- Authority
- DE
- Germany
- Prior art keywords
- formaldehyde
- soluble
- condensation products
- production
- phenols
- 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
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- 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
- C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
- C08G16/02—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes
- C08G16/0212—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds
- C08G16/0218—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds containing atoms other than carbon and hydrogen
- C08G16/0225—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with acyclic or carbocyclic organic compounds containing atoms other than carbon and hydrogen containing oxygen
-
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/10—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with phenol
-
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/12—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with monohydric phenols having only one hydrocarbon substituent ortho on para to the OH group, e.g. p-tert.-butyl phenol
-
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/38—Block or graft polymers prepared by polycondensation of aldehydes or ketones onto macromolecular compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Emergency Medicine (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Description
Es ist bekannt, . Kondensationsprodukte aus Phenolen, Formaldehyd und trocknenden ölen bzw.' deren Oxydatiohsprodtikten herzustellen. Diese bekannten Verfahren führen entweder zu flüssigen Kondensationsprodukten (vgl.amerikanischePatentschrift 1212738) oder aber zu kautschukärtigen Erzeugnissen (vgl. amerikanische Patentschrift 1 086 139) oder zu, insbesondere in Lösungsmitteln, wie Aceton, Essigsäureestern usw., unlöslichen, mehr oder weniger weichen plastischen Massen (vgl. britische Patentschrift 136 298 und Patentschrift 269659). Bei allen diesen bekannten Verfahren wird von ölen oder von deren flüssigen Oxydationsprodukten ausgegangen. Dagegen ist es bisher noch nicht gelungen, aus den genannten drei Ausgangsstoffen harzartigeKondensationsprodukte herzustellen, die in den üblichen Lösungsmitteln löslich sind und infolge dieser Löslichkeit als Grundstoffe in der Lackindustrie Verwendungfinden können.It is known, . Condensation products from phenols, formaldehyde and drying agents oil or ' to produce their oxidation products. These known processes either lead to liquid condensation products (see American patent specification 1212738) or to rubber-based products (see American patent specification 1 086 139) or to, especially in solvents such as acetone, acetic acid esters, etc., insoluble, more or less soft plastic masses (see British patent specification 136 298 and Patent 269659). With all these well-known The process is based on oils or their liquid oxidation products. On the other hand, it has not yet been possible to use the three starting materials mentioned to produce resinous condensation products in common solvents are soluble and as a result of this solubility are used as raw materials in the paint industry can.
Es wurde gefunden, daß derartige lösliche Kondensationsprodukte erhalten werden können, wenn man Lösungen von festen Oxydationsprodukten des Leinöls (Linoxyn) oder anderer trocknender öle, wie z. B. von Holzöl (sogenannte Oxyne) in Phenol, Kresolen usw. mit Formaldehyd, seinen Polymeren oder Derivaten oder mit Stoffen, die Formaldehyd abspalten, erwärmt. Phenol, Phenol-, homologe und Derivate von Phenol und Phenolhomologen erwiesen sich nämlich als ausgezeichnete Lösungsmittel für Linoxyn und ähnliche feste Oxydationsprodukte trocknender öle; es gelingt beispielsweise, in geschmolzenem Phenol mehr als die gleiche Menge Linoxyn zur Auflösung zu bringen. Die so erhaltenen sirupartigen Massen sind löslich in Aceton, Butylacetat und ähnlichen Lösungsmitteln, lassen sich aber technisch kaum verwerten, zumal da es unmöglich ist, sie durch einfaches Erhitzen in brauchbare feste Stoffe zu überführen. Man kann aber aus ihnen wertvolle Kondensationsprodukte gewinnen, wenn man sie — unter Zusatz basischer Katalysatoren, wie von Ammoniak — mit Formaldehyd, seinen Polymeren oder Derivaten oder Formaldehyd abspaltenden Stoffen erwärmt. Durch Abänderung der Reaktionstemperatur und der Erhitzungsdauer kann man hierbei zu den verschiedensten Reaktionsprodukten gelangen; je länger und je höher man erhitzt, um so härter und weniger löslich sind die entstehenden harzartigen Kondensationsprodukte. Will man Harze erzielen, die in den üblichen flüchtigen Lösungsmitteln löslich sind, so muß man nicht länger als 2 bis 3 Stunden auf etwa 1200 erhitzen. Besonders günstig verläuft die Reaktion, wenn man zu dem Reaktionsgemisch noch einige...Pr,Qzent Paraformaldehyd zugibt.It has been found that such soluble condensation products can be obtained if solutions of solid oxidation products of linseed oil (Linoxyn) or other drying oils, such as. B. of wood oil (so-called oxynes) in phenol, cresols, etc. with formaldehyde, its polymers or derivatives or with substances that split off formaldehyde, heated. Phenol, phenol, homologues and derivatives of phenol and phenol homologues have proven to be excellent solvents for linoxyn and similar solid oxidation products of drying oils; For example, it is possible to dissolve more than the same amount of Linoxyn in molten phenol. The syrupy masses obtained in this way are soluble in acetone, butyl acetate and similar solvents, but can hardly be used industrially, especially since it is impossible to convert them into usable solid substances by simple heating. However, valuable condensation products can be obtained from them if they are heated with formaldehyde, its polymers or derivatives or substances which split off formaldehyde - with the addition of basic catalysts, such as ammonia. A wide variety of reaction products can be obtained by changing the reaction temperature and the heating time; the longer and the higher the temperature, the harder and less soluble are the resulting resinous condensation products. If one wishes to obtain resins which are soluble in the usual volatile solvents, it must be no longer than 2 to 3 hours, heated to about 120 0th The reaction proceeds particularly favorably if a few more...
Beispiel ιExample ι
50 kg Linoxyn werden mit 50 kg technischem Phenol erwärmt, bis vollständige Lösung eingetreten ist. Zu der braunen Lösung gibt man 50 kg Formaldehyd (40 Vol. "I0Ig) sowie 0,25 kg Ammoniak (18 °/oig) und erhitzt etwa 3 Stunden auf 90 bis ioo°. Es bildet sich dann ein sirupartiges, braunes in Aceton, Essigsäureestern, Gemischen von50 kg of Linoxyn are heated with 50 kg of technical phenol until complete dissolution has occurred. To the brown solution added 50 kg of formaldehyde gives (40 Vol. "I 0 Ig) and 0.25 kg ammonia (18 ° / o solution) and heated for about 3 hours at 90 to ioo °. It then forms a syrupy, brown in acetone, acetic acid esters, mixtures of
to Kohlenwasserstoffen und Alkoholen usw. lösliches Produkt A, dessen Lösungen als Lack Verwendung finderi können; werden die damit überzogenen Gegenstände einer Temperatur von 140 bis i6o° ausgesetzt, so geht der Überzug in eine hochglänzende, feste Lackschicht über. Erhitzt man A 2 bis 3 Stunden auf etwa 120°, so erhält man ein festes, in den eben genannten Lösungsmitteln lösliches Harz B, das unmittelbar zur Herstellung vonto hydrocarbons and alcohols etc. soluble product A, its solutions as varnish Use finderi can; the objects coated with it become one temperature exposed from 140 to 160 °, the coating turns into a high-gloss, solid layer of varnish above. If A is heated to about 120 ° for 2 to 3 hours, a solid, in Resin B soluble in the solvents mentioned above, which is used directly for the production of
ao Lacken, Imprägnierungs- und Wasserdichtmachungsmitteln verwendet werden kann. · B kann außerdem bei der Linoleumfabrikation zur Herstellung des Linoleumzementes an Stelle von Kopalen, Kolophonium usw. Verwendung finden. Bei längerem Erhitzen von A und B auf etwa i6o° entsteht ein hartes, unschmelzbares und sehr schwer lösliches Harz C, das ebenso wie A und B unlöslich in Ammoniak und Alkalicarbonatlösung ist, aber von Alkalilauge gelöst wird.ao varnishes, impregnation and waterproofing agents can be used. · B can also be used in linoleum production for the production of linoleum cement Place of copals, rosin, etc. find use. With prolonged heating of A and B at about i6o ° creates a hard, Infusible and very sparingly soluble resin C, which, like A and B, is insoluble is in ammonia and alkali carbonate solution, but is dissolved by alkali lye.
In 50 kg warmem Phenol werden 30 kgIn 50 kg of warm phenol, 30 kg
Holzöl-Oxyn gelöst. · Die Lösung wird mit 20 kg 4O°/0igem Formaldehyd unter Zusatz von 10 kg konzentriertem, wässerigem Ammoniak kondensiert. Nach Beendigung der unter starkem Erwärmen vor sich gehenden Reaktion wird zwecks Entfernung des Wassers auf 105 ° erhitzt, worauf das A-Erzeugnis als zähflüssige, fadenziehende Masse erhalten wird. Durch weiteres Erhitzen auf 120 bis 1300 geht es in das B-Erzeugnis über; bei noch weiter fortgesetztem Erhitzen auf 160 bis i8o° erhält man C-Erzeugnis. B und C sind harte, klare Harze von rötlichbrauner Farbe. Wood oil oxyn dissolved. · The solution with 20 kg of 4O ° / 0 formaldehyde with addition of 10 kg of concentrated, aqueous ammonia condensed. After the reaction, which is taking place under intense heating, is completed, the water is removed by heating to 105 °, whereupon the A-product is obtained as a viscous, stringy mass. By further heating to 120 to 130 0 it changes into the B product; if the heating is continued at 160 to 180 °, a C product is obtained. B and C are hard, clear resins of reddish brown color.
A löst sich leicht in Gemischen von Äthylalkohol undBenzolkohlenwasserstoffen. Außerdem sind die Ester der Essigsäure (Methyl-, Äthylacetat usw.) in Gemischen mit Kohlenwasserstoffen ausgezeichnete Lösungsmittel sowohl für das A- wie für das B-Erzeugnis. Das Harz C ist in allen Lösungsmitteln unlöslich. Die Harze sind beständig gegen Säuren, wie Essigsäure, Salzsäure, Schwefelsäure u. dgl.A readily dissolves in mixtures of ethyl alcohol and benzene hydrocarbons. aside from that are the esters of acetic acid (methyl, ethyl acetate, etc.) in mixtures with hydrocarbons excellent solvents for both the A and B product. Resin C is insoluble in all solvents. The resins are resistant to acids such as acetic acid, hydrochloric acid, sulfuric acid and the like.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB126206D DE534784C (en) | 1926-06-30 | 1926-06-30 | Process for the production of soluble, resinous condensation products from phenols and formaldehyde |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB126206D DE534784C (en) | 1926-06-30 | 1926-06-30 | Process for the production of soluble, resinous condensation products from phenols and formaldehyde |
Publications (1)
Publication Number | Publication Date |
---|---|
DE534784C true DE534784C (en) | 1931-10-01 |
Family
ID=6996638
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEB126206D Expired DE534784C (en) | 1926-06-30 | 1926-06-30 | Process for the production of soluble, resinous condensation products from phenols and formaldehyde |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE534784C (en) |
-
1926
- 1926-06-30 DE DEB126206D patent/DE534784C/en not_active Expired
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