DE666254C - Process for the treatment of resinous condensation products from phenols and aldehydes - Google Patents
Process for the treatment of resinous condensation products from phenols and aldehydesInfo
- Publication number
- DE666254C DE666254C DEB156710D DEB0156710D DE666254C DE 666254 C DE666254 C DE 666254C DE B156710 D DEB156710 D DE B156710D DE B0156710 D DEB0156710 D DE B0156710D DE 666254 C DE666254 C DE 666254C
- Authority
- DE
- Germany
- Prior art keywords
- condensation products
- water
- treatment
- aldehydes
- 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
- 239000007859 condensation product Substances 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 6
- 150000002989 phenols Chemical class 0.000 title claims description 3
- 150000001299 aldehydes Chemical class 0.000 title claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 11
- 230000001476 alcoholic effect Effects 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000007865 diluting Methods 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- -1 phenol aldehyde Chemical class 0.000 description 2
- 229920003987 resole Polymers 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 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
- 230000010494 opalescence Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000926 separation method Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Description
Bekanntlich sind die primären harzartigen Kondensationsprodukte aus Phenolen und Aldehyden, sei es, daß die Kondensation in saurem, sei es, daß sie in alkalischem Medium stattgefunden hat, in Alkohol und Alkalien leicht löslich, nicht aber in Wasser, so daß alkoholische Lösungen der genannten Kondensationsprodukte beim Verdünnen mit Wasser sich unter Ausscheidung von Flocken stark trüben und ίο bei weitgehender Verdünnung eine nahezu vollkommene Ausscheidung der Harze stattfindet. Die Erfindung besteht nun darin, daß man die in verdünnten wäßrigen Lösungen fixer Alkalien, z. B. in 5 — io%iger Natronlauge, gelösten Kondensationsprodukte auf dem Wasserbade oder am Rückflußkühler so lange erhitzt, bis eine Probe der Kondensationsprodukte nach dem Ausfällen und Auswaschen mit Wasser beim Verdünnen der alkoholischen Lösung mit be-It is well known that the primary resinous condensation products of phenols and aldehydes, be it that the condensation took place in an acidic medium, be it that it took place in an alkaline medium has, easily soluble in alcohol and alkalis, but not in water, so that alcoholic Solutions of the condensation products mentioned are reduced when diluted with water Excretion of flakes is very cloudy and ίο with extensive dilution an almost perfect Excretion of the resins takes place. The invention consists in that one fixer in dilute aqueous solutions Alkalis, e.g. B. in 5 - 10% sodium hydroxide solution, dissolved condensation products on the water bath or heated on the reflux condenser until a sample of the condensation products appears the precipitation and washing out with water when diluting the alcoholic solution with
ao liebigen Mengen Wasser keine Trübung mehr erkennen läßt. Die so behandelten Harze sind auch in etwa 8o°/0iger Essigsäure löslich und scheiden sich auch aus dieser sauren Lösung auf Zusatz von Wasser nicht aus. Werden die Lösungen der so behandelten Harze in Alkohol oder in Essigsäure nach dem Verdünnen mit Wasser bei niederen Temperaturen zweckmäßig im Vakuum eingedampft, so erhält man schließlich konzentrierte, rein wäßrige Lösungen mit mehr oder weniger starker Opaleszenz oder von milchartigem Aussehen. Dies gilt insbesondere für diejenigen Kondensationsprodukte, die in alkalischem Medium (z. B. Ammoniak oder Natronlauge) entstanden sind, während die in saurem Medium entstandenen Kondensationsprodukte sich weniger rasch verändern. Es unterliegt wohl keinem Zweifel, daß es sich hier um kolloide Lösungen der Kondensationsprodukte handelt. ao lovable amounts of water no longer shows any turbidity. The treated resins are also soluble in about 8o ° / 0 acetic acid and deposit even from this acidic solution on addition of water is not enough. If the solutions of the resins treated in this way in alcohol or in acetic acid, after dilution with water, are expediently evaporated in vacuo at low temperatures, then concentrated, purely aqueous solutions with a more or less strong opalescence or a milky appearance are finally obtained. This applies in particular to those condensation products that are formed in an alkaline medium (e.g. ammonia or sodium hydroxide solution), while the condensation products that are formed in an acidic medium change less rapidly. There is no doubt that these are colloidal solutions of the condensation products.
Durch diese tiefgreifende Veränderung der Löslichkeitseigenschaften unterscheiden sich die nach dem beanspruchten Verfahren erhältlichen Produkte von allen bisher bekannten Phenolaldehydharzen. Due to this profound change in the solubility properties, the products obtainable by the claimed process from all previously known phenol aldehyde resins.
Zwar ist im Friedländer, Band 16, S. 1999 der Anspruch einer Patentanmeldung B 121 570 angeführt, wonach die in Gegenwart basischer Katalysatoren aus Phenol und Formaldehyd erhältlichen harzartigenKondensationsprodukte (Resole) in wäßriger alkalischer Lösung erhitzt werden sollen. Jedoch enthält der Patentanspruch keine näheren Angaben über die Durchführung des Verfahrens, vor allem über die Temperatur und über die Zeitdauer des Erhitzens sowie über die Merkmale, an denen das Ende der Behandlung erkannt werden kann.It is in Friedländer, Volume 16, p. 1999 the claim of a patent application B 121 570 cited, according to which in the presence of basic Resinous condensation products obtainable from phenol and formaldehyde catalysts (Resole) are to be heated in an aqueous alkaline solution. However, the claim contains no details about the implementation of the process, especially about the temperature and the duration of the heating as well as the characteristics by which the end of treatment can be recognized.
Daß aber auch die Beschaffenheit der ursprünglichen Resole für den Erfolg der Behandlung von ausschlaggebender Bedeutung ist, geht z. B. daraus hervor, daß diejenigen Phenolaldehydharze, die aus Phenol und Formaldehyd in Gegenwart so großer Mengen Alkalihydroxyd entstanden sind, daß keine- Abscheidung der entstandenen Harze stattfindet, beim längeren Weitererhitzen mit verdünntem Alkali nicht in die wertvollen neuen Produkte übergehen,But also the nature of the original resol is essential for the success of the treatment is of crucial importance, z. B. from the fact that those phenol aldehyde resins which have arisen from phenol and formaldehyde in the presence of so large amounts of alkali metal hydroxide that no separation of the resulting resins takes place, if the heating is continued for a longer period with diluted alkali, this does not occur move on to the valuable new products,
sondern unter den eben genannten Bedingungen allmählich ihre Löslichkeit in Alkohol einbüßen oder bereits aus der ätzalkalischen ~Lö^A sung sich in Form einer unlöslichen Gallerte: ausscheiden, womit also genau die entgegen« gesetzte Wirkung wie bei dem beanspruchten Verfahren erzielt wird.but gradually lose under the aforementioned conditions their solubility in alcohol or already from the ätzalkalischen Lö ~ ^ A solution in the form of an insoluble curd: excrete, which thus exactly the opposite "set effect as in the claimed process.
loo g des Kondensationsproduktes aus Formaldehyd und Kresol, entstanden in ammoniakalischem Medium, werden in il 6% ig r Natronlauge gelöst und nach erfolgter Lösung auf dem kochenden Wasserbade oder, um die Reaktion zu beschleunigen, am Rückflußkühler erhitzt. Schon nach wenigen Stunden laßt eine mit Säure versetzte, mit Wasser ausgewaschene und bei niedriger Temperatur getrocknete Probe erkennen, daß die alkoholische Lösung beim Verdünnen mit Wasser klar bleibt oder nur eine schwache Trübung erleidet. Man erhitzt die alkalische Lösung so lange, bis die gemäß obigen Angaben auf gearbeitete Probe beim Verdünnen der alkoholischen Lösung mit Wasser vollkommen klar bleibt. Sobald dieser Punkt erreicht ist, wird das Harz durch Zugabe von Säuren vollkommen ausgefällt, mit Wasser ausgewaschen und bei niedriger Temperatur getrocknet. Das so gewonnene Produkt läßt sich leicht zu einem staubfeinen Pulver zerreiben. Es ist in Methyl- ;: und Äthylalkohol sowie in Alkalien leicht löslieh. Beim Erhitzen auf höhere Temperaturen ,sintert es, ohne vollkommen zu schmelzen. •"'Wird das Erhitzen auf höhere Temperaturen, d.h. auf Temperaturen über 100°, längere Zeit fortgesetzt, so wird das Harz allmählich in Alkohol und Alkalien unlöslich.100 g of the condensation product of formaldehyde and cresol, formed in ammoniacal Medium, are dissolved in 6% sodium hydroxide solution and after dissolution has taken place the boiling water bath or, to accelerate the reaction, on the reflux condenser heated. Already after a few hours leave an acid mixed with water washed out with water and samples dried at low temperature recognize that the alcoholic solution remains clear when diluted with water or suffers only a weak haze. The alkaline solution is heated until the according to the above information on the processed sample when diluting the alcoholic solution with water remains perfectly clear. Once this point is reached, the resin is made by adding acids completely precipitated, washed out with water and dried at low temperature. That so The product obtained can easily be ground to a fine powder. It's in methyl ;: and ethyl alcohol as well as easily soluble in alkalis. When heated to higher temperatures, it sinters without completely melting. • "'If the heating to higher temperatures, i.e. to temperatures above 100 °, is used for a longer period of time continued, the resin gradually becomes insoluble in alcohol and alkalis.
Die gemäß dem beschriebenen Verfahren erhältlichen Produkte sollen als sogenannte Kunststoffe sowie zu den verschiedensten Zwecken, insbesondere auf dem Gebiet der Färberei und verwandten Gebieten, Verwendung finden.The products obtainable according to the process described are said to be so-called plastics as well as for a wide variety of purposes, especially in the field of dyeing and related areas.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB156710D DE666254C (en) | 1932-07-24 | 1932-07-24 | Process for the treatment of resinous condensation products from phenols and aldehydes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB156710D DE666254C (en) | 1932-07-24 | 1932-07-24 | Process for the treatment of resinous condensation products from phenols and aldehydes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE666254C true DE666254C (en) | 1938-10-14 |
Family
ID=7003576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEB156710D Expired DE666254C (en) | 1932-07-24 | 1932-07-24 | Process for the treatment of resinous condensation products from phenols and aldehydes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE666254C (en) |
-
1932
- 1932-07-24 DE DEB156710D patent/DE666254C/en not_active Expired
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