DE400639C - Process for the preparation of derivatives of the resinous, alkali-soluble condensation products of phenols and aldehydes - Google Patents
Process for the preparation of derivatives of the resinous, alkali-soluble condensation products of phenols and aldehydesInfo
- Publication number
- DE400639C DE400639C DEB102847D DEB0102847D DE400639C DE 400639 C DE400639 C DE 400639C DE B102847 D DEB102847 D DE B102847D DE B0102847 D DEB0102847 D DE B0102847D DE 400639 C DE400639 C DE 400639C
- Authority
- DE
- Germany
- Prior art keywords
- alkali
- phenols
- condensation products
- aldehydes
- resinous
- 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
- 239000007859 condensation product Substances 0.000 title claims description 8
- 150000002989 phenols Chemical class 0.000 title claims description 6
- 150000001299 aldehydes Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title description 7
- 238000002360 preparation method Methods 0.000 title description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 5
- 239000000969 carrier Substances 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- 239000004922 lacquer Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000002966 varnish Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229930016911 cinnamic acid Natural products 0.000 description 3
- 235000013985 cinnamic acid Nutrition 0.000 description 3
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- OGGXGZAMXPVRFZ-UHFFFAOYSA-N dimethylarsinic acid Chemical compound C[As](C)(O)=O OGGXGZAMXPVRFZ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- -1 naphthalenesulfonyl Chemical group 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- WMFATTFQNRPXBQ-UHFFFAOYSA-N 2-bromopentanoic acid Chemical compound CCCC(Br)C(O)=O WMFATTFQNRPXBQ-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- 241000272165 Charadriidae Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 229950004243 cacodylic acid Drugs 0.000 description 1
- 150000004651 carbonic acid esters Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229940082150 encore Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000011276 wood tar Substances 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/28—Chemically modified polycondensates
-
- 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
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
- C08G14/06—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols and monomers containing hydrogen attached to nitrogen
-
- 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
- C08G8/28—Chemically modified polycondensates
- C08G8/32—Chemically modified polycondensates by organic acids or derivatives thereof, e.g. fatty oils
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Cosmetics (AREA)
Description
Verfahren zur Darstellung von Derivaten der harzartigen, in Alkali löslichen Kondensationsprodukte aus Phenolen und Aldehyden. Den Gegenstand des Hauptpatents 391072 bildet ein Verfahren zur Überführung der primären alkalilöslichen Kondensationsprodukte aus Phenolen und Formaldehyd in neue Verbindungen, in denen die freien Hydroxylgruppen der Ausgangsstoffe ganz oder teilweise durch organische Reste beliebiger Art verschlossen sind, und im Zusatzpatent 399677 ist weiter gezeigt, daß sich die harzartigen Kondensationsprodukte aus Phenolen und anderen Aldehyden in analog zusammengesetzte Verbindungen überführen lassen. Unter der großen Zahl der diesen Zweck erfüllenden Reste gibt es nun solche, deren Wirkung mit dem Verschluß der Hydroxylgruppen als erschöpft angesehen werden kann, wie z. B. den Formyl-, Acetyl-, Benzoyl-, den Benzol-, Toluol- und Naphthalinsulfonyl-, den Methyl-, Äthyl-, Propyl-, Benzylrest usw.Process for the preparation of derivatives of the resinous, in alkali soluble condensation products from phenols and aldehydes. The subject of the main patent 391072 forms a process for the conversion of the primary alkali-soluble condensation products from phenols and formaldehyde into new compounds in which the free hydroxyl groups the starting materials completely or partially closed by organic residues of any kind are, and in the additional patent 399677 is further shown that the resinous condensation products convert from phenols and other aldehydes into compounds with an analogous composition permit. Among the great number of remnants fulfilling this purpose there are now those whose effect can be considered exhausted with the closure of the hydroxyl groups can, such as B. the formyl, acetyl, benzoyl, the benzene, toluene and naphthalenesulfonyl, the methyl, ethyl, propyl, benzyl radical, etc.
Die weitere Verfolgung des Erfindungsgedankens führte dazu, auch solche organischen Verbindungen zum Verschluß der Hydroxylgruppen heranzuziehen, bei denen weniger der Einfluß auf die Löslichkeitsverhältnisse der neuen Reaktionsprodukte (in organischen Mitteln und in Alkali) im Vordergrunde steht, sondern die an sich Träger bestimmter wertvoller Eigenschaften und Wirkungen sind, wie z. B. die Valeriansäure und Bromvaleriansäure, die Zimtsäure, die Salicylsäure, die Mandelsäure und viele andere Carbonsäuren, die als Träger von Heilwirkungen bekannt sind; ferner solche, die als Farbstoffkomponenten Verwendung finden, wie z. B. Amino-, Diamino-, Oxy-, Dioxy-, Aminooxyverbindungen der aromatischen Reihe oder deren Sulfonsäuren. Die Verwirklichung des ebener"vähnten Zweckes setzt lediglich voraus, daß die zum Verschluß der Hydroxylgruppen ausersehenen Verbindungen in üblicher Weise in eine reaktionsfähige Form übergeführt werden (für die Carbonsäuren ist dies in der Regel das Säurechlorid oder -anhydrid), die ihnen den Eintritt in die Hydroxylgruppen gestatten. Als zweite Bedingung kommt hinzu die Forderung, daß die besonderen Wirkungen der betreffenden Verbindungen dem verschließenden Reste bzw. dem Gesamtmolekül erhalten bleiben oder zu gewünschtem Zeitpunkte in die Erscheinung zu treten vermögen. Diesen Forderungen zu genügen, sind aber zahlreiche, für den vorliegenden Zweck an sich geeignete Verbindungen nicht ohne weiteres imstande. Entweder entbehren sie der erforderlichen Reaktionsfähigkeit gegenüber dem phenolischen Hydroxyl, oder sie verlieren, trenn sie nach ihrer Überführung in die geeignete reaktionsfähige Form die Rolle des verschließenden Restes iiberno!ninen haben, völlig oder wenigstens teilweise ihre früheren Wirkungen, auf denen ihr besonderer Wert beruht.The further pursuit of the inventive idea led to this, too to use organic compounds to close the hydroxyl groups in which less the influence on the solubility ratios of the new reaction products (in organic agents and in alkali) is in the foreground, but that in itself Are carriers of certain valuable properties and effects, such as B. valeric acid and bromovaleric acid, cinnamic acid, salicylic acid, mandelic acid and many other carboxylic acids known to have medicinal properties; also those which are used as dye components, such as. B. Amino, diamino, oxy, Dioxy, aminooxy compounds of the aromatic series or their sulfonic acids. the Realization of the just "mentioned purpose only presupposes that the closure The compounds selected from the hydroxyl groups are converted into a reactive one in the usual manner Form (for the carboxylic acids this is usually the acid chloride or anhydride), which allow them to enter the hydroxyl groups. Second Condition is added the requirement that the special effects of the relevant Connections to the closing residues or the entire molecule are retained or be able to appear at the desired times. These demands to be sufficient, however, are numerous compounds which are suitable per se for the present purpose not easily able. Either they lack the necessary responsiveness versus the phenolic hydroxyl, or they lose, disconnect them after their conversion into the appropriate reactive form, the role of the occluding Remnants of iibernonines have, wholly or at least in part, their earlier effects, on which their particular worth is based.
Die eben geschilderten Schwierigkeiten lassen sich aber auch in dem vorliegenden Falle überwinden, wenn inan die zum Verschluß der Hydroxylgruppen bestimmten Verbindungen nicht unmittelbar, sondern nur mittelbar, d. h. unter Benutzung eines Hilfsstoffes, mit den primären Kondensationsprodukten zu neuen komplexen Verbindungen zusammenschließt. Handelt es sich z. B., tun einen denkbar einfachsten Fall zu nennen, darum, die offenen Hydroxylgruppen eines primären Kondensationsproduktes mit Hilfe von Phenol zu verschließen, so ist letzteres unmittelbar als solches dazu nicht imstande. Es würde vielmehr der Anwendung ganz besonderer Mittel bedürfen, um die Vereinigung der beiden ILOtnpoiienten herbeizuführen. Gleichzeitig aber würde der Plienvlrest des in Form eines Plienolätliers gebundenen Phenols den größten Teil seiner früheren Wirksamkeit, etwa als Desinfiziens, einbüßen, wenn man unter entsprechenden Bedingungen davon Gebrauch zu machen wünschte. Bedient man sich aber, wie bereits ini "Zusatzpatent 399677 ebenfalls gezeigt ist, zur Erreichung des angestrebten Zweckes eines Hilfsstoffes, der die Rolle des verbindenden Gliedes zwischen den beiden zu vereinigenden Komponenten übernimmt, so gelingt die Lösung der gestellten Aufgabr ohne besondere Schwierigkeit. L'ber die außerordentlich große -Mannigfaltigkeit in der Ausführung des Verfahrens finden sich niiliere Angaben bereits im Zusatzpatent 399a7;, desleichen über die unterschiedliche Wider-Z, standsfähigkeit der komplexen -Verbindungen gegenüber hydrolytisch spaltenden -Mitteln. Beispiel i (Zimtsäure).The difficulties just described can also be found in the Overcome the present case if inan the intended for the closure of the hydroxyl groups Connections not directly, but only indirectly, d. H. using a Auxiliary, with the primary condensation products to form new complex compounds merges. Is it z. B., do the simplest possible case to name, therefore, using the open hydroxyl groups of a primary condensation product to be closed by phenol, the latter is not directly as such able. Rather, it would require the use of very special means to the To bring about the union of the two ILO participants. At the same time, however, would Plienvlrest of the phenol bound in the form of a Plienolätliers the largest part its former effectiveness, for example as a disinfectant, forfeit if you use the appropriate Conditions to make use of it. But if you use it, as already ini "additional patent 399677 is also shown to achieve the desired Purpose of an auxiliary material that plays the role of the connecting link between the takes over the two components to be combined, the solution to the problem is successful Abandoned without any particular difficulty. About the extraordinarily large variety In the implementation of the process, detailed information can already be found in the additional patent 399a7;, same about the different resistance of the complex Compounds against hydrolytically cleavage agents. Example i (cinnamic acid).
14,8,c,1 Zimtsäure werden mit 20,8- Phospliorpentachlorid vermischt, wobei unter lebhafter Salzsäureentwicklung sich das Zimtsäurechlorid bildet. In die flüssige -Mischung werden unter stetem Umruhren 12- feingepulvertes Fornialdehvd-Kresol-Harz eingetragen. Uan erhitzt auf dem Wasserbade, bis die Reaktion beendigt ist. -Nach dein Erkalten wird die Schmelze zerkleinert und zur Entfernung der Phosphorverbindungen mehrere --Male finit heißem Wasser ausgezogen. Das Reaktionsprodukt, (las als Zinitsäurepräparat dienen soll, stellt in rohem Zustande ein amorphes, orangerotes, wasserunlösliches Pulver dar, das sich bei ioo' trocknen liißt, ohne zu schmelzen. Beispiel 2 (Borneo-).14.8, c, 1 cinnamic acid are mixed with 20.8 phosphorus pentachloride, the cinnamic acid chloride being formed with vigorous evolution of hydrochloric acid. 12 finely powdered fornialdehyde-cresol resin are added to the liquid mixture with constant stirring. Uan is heated on the water bath until the reaction has ended. -After it has cooled down, the melt is crushed and drawn out with finely hot water several times to remove the phosphorus compounds. The reaction product (intended to be used as a zinitic acid preparation) is, in its raw state, an amorphous, orange-red, water-insoluble powder which can be dried at 100 'without melting. Example 2 (Borneo).
j2"" Foi-inaldehv(1-Kresol-Harz und 15,4g, Borneo- wer;len innig gemischt und in eine 1'oltiollö stieg, enthaltend etwa 18 Prozent Phosgen, ein-etragen. Man läßt längere Zeit bei gewöhnlicher Temperatur oder mäßiger Wärme stehen, bis eine Probe des Reaktionsproduktes sich als alkaliunlöslich erweist. Aldann wird (-las Toluol, in dein ein Teil des gemischten Kohlensäureesters gelöst ist, verdampft, (ler Rückstand mit verdünnter So(lalösung gewaschen und getrocknet. Das Reaktionsprodukt stellt ein bräunlicligelbes, in Nasser unlösliches Harz dar, das in heißer Solvent-Naaphtlia und in Tetralin löslich ist. Beispiel 3 (2 - Amino - 5 - oxynaplithalin-7-sulfonsäure). 12- Forinaldehyd-Kresol-Harz und 26 g 2 Ainino-5-oxvnaphthalin-7-sulfonsäure werden vermittels 12 g Natronhydrat und ioo ccm Wasser in Lösung gebracht. Zach Zugabe von 19 g Äthvlenbromid wird so lange am Rückflußkühler erhitzt, bis alles ü1 verschwunden ist. Man säuert niit Salz- oder Schwefelsäure an, wodurch (las Reaktionsprodukt, das in Soda leicht, jedoch in Wasser sehr schwer löslich ist, vollkommen ausgeschieden wird. Es unterscheidet sich von der Am,inooxynaphthalinsulfons;iure selbst durch den merklich blaustichigeren Ton der beim Kuppeln mit Diazoniuniverl)in(l@tingen erhältlichen Azofarbstoffe.j2 "" Foi-inaldehv (1-cresol resin and 15.4g, Borneowers; len intimately mixed and in a 1'oltiollö rose, containing about 18 percent phosgene, entered. Man let stand for a long time at ordinary temperature or moderate heat until a Sample of the reaction product proves to be insoluble in alkali. Aldann will (-las Toluene, in which part of the mixed carbonic acid ester is dissolved, evaporates, (The residue was washed with dilute sol solution and dried. The reaction product represents a brownish-yellow resin that is insoluble in water, which in hot solvent Naaphtlia and is soluble in tetralin. Example 3 (2 - amino - 5 - oxynaplithalin-7-sulfonic acid). 12-formaldehyde-cresol resin and 26 g of 2-amino-5-oxynaphthalene-7-sulfonic acid brought into solution by means of 12 g sodium hydrate and 100 ccm water. Zach encore 19 g of ethylene bromide is heated in the reflux condenser until everything has disappeared is. It is acidified with hydrochloric or sulfuric acid, whereby (the reaction product, which is easily soluble in soda, but very sparingly soluble in water, is completely eliminated will. It differs from the Am, inooxynaphthalinsulfons; iure itself by the noticeably more bluish tone when coupling with Diazoniuniverl) in (l @ tingen available azo dyes.
Von dein Verfahren der Patentschrift 3io28z unterscheidet sich (las vorliegende dadurch, clala hier in Alkali unlösliche Produkt,-i Ester) erbalten wer(len, ,während nach dein bekannten Verfahren hirch Einwirkung vor. Kakodylsäure auf schmelzbare Kondensationsprodukte aus Phenolen und Formaldehyd arsenhaltige, in Alkali lösliche Produkte entstehen, deren angebliche esterartige Natur nicht näher aufgeklärt ist.Your method of patent specification 3io28z differs (read present thereby, clala here in alkali insoluble product, -i ester) inherited who (len, while according to your known procedure hirch action before. Cacodylic acid on fusible condensation products of phenols and formaldehyde containing arsenic, Products which are soluble in alkali are formed, but their alleged ester-like nature is not is clarified in more detail.
Auch die in der Patentschrift 223838 der Klasse 12d erwähnten. aus wasserhaltigen Holzteerölen durch Erhitzen mit Benzoesätire oler Salicylsäure find weitere Kondensation finit I-,oi-nialdeliyd erhältlichen Produkte stelzen in keiner näheren Beziehung zu den gemäß vorliegendem Verfahren entstehenden Verbindungen.Also those mentioned in Class 12d patent specification 223838. the end water-containing wood tar oils by heating with Benzoesätire oler salicylic acid further condensation finite I-, oi-nialdeliyd available products stilt in none closer relationship to the compounds formed according to the present process.
Claims (1)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB102847D DE400639C (en) | 1918-06-10 | 1919-03-22 | Process for the preparation of derivatives of the resinous, alkali-soluble condensation products of phenols and aldehydes |
| GB2028620A GB148366A (en) | 1918-06-10 | 1920-07-09 | Process for the production of new derivatives of the condensation products of aldehydes and phenols |
| FR520319A FR520319A (en) | 1918-06-10 | 1920-07-10 | Process for the production of derivatives of the condensation products of formaldehydes and phenols |
| CH94457D CH94457A (en) | 1918-06-10 | 1920-07-13 | Process for the preparation of a benzyl derivative of the condensation product of formaldehyde and cresol. |
| AT101628D AT101628B (en) | 1918-06-10 | 1920-07-14 | Process for the preparation of derivatives of the resinous, alkali-soluble condensation products of formaldehyde and phenols. |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB86582D DE391072C (en) | 1918-06-10 | 1918-06-10 | Process for the preparation of derivatives of the resinous, alkali-soluble condensation products of phenols and formaldehyde |
| DEB88830D DE399677C (en) | 1918-06-10 | 1919-03-22 | Process for the preparation of derivatives of the resinous, alkali-soluble condensation products of phenols and aldehydes |
| DEB102847D DE400639C (en) | 1918-06-10 | 1919-03-22 | Process for the preparation of derivatives of the resinous, alkali-soluble condensation products of phenols and aldehydes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE400639C true DE400639C (en) | 1924-08-18 |
Family
ID=27209346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB102847D Expired DE400639C (en) | 1918-06-10 | 1919-03-22 | Process for the preparation of derivatives of the resinous, alkali-soluble condensation products of phenols and aldehydes |
Country Status (5)
| Country | Link |
|---|---|
| AT (1) | AT101628B (en) |
| CH (1) | CH94457A (en) |
| DE (1) | DE400639C (en) |
| FR (1) | FR520319A (en) |
| GB (1) | GB148366A (en) |
-
1919
- 1919-03-22 DE DEB102847D patent/DE400639C/en not_active Expired
-
1920
- 1920-07-09 GB GB2028620A patent/GB148366A/en not_active Expired
- 1920-07-10 FR FR520319A patent/FR520319A/en not_active Expired
- 1920-07-13 CH CH94457D patent/CH94457A/en unknown
- 1920-07-14 AT AT101628D patent/AT101628B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| AT101628B (en) | 1925-11-10 |
| FR520319A (en) | 1921-06-23 |
| CH94457A (en) | 1922-05-01 |
| GB148366A (en) | 1922-01-09 |
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