DE474787C - Process for refining recent natural resins - Google Patents
Process for refining recent natural resinsInfo
- Publication number
- DE474787C DE474787C DEC33190D DEC0033190D DE474787C DE 474787 C DE474787 C DE 474787C DE C33190 D DEC33190 D DE C33190D DE C0033190 D DEC0033190 D DE C0033190D DE 474787 C DE474787 C DE 474787C
- Authority
- DE
- Germany
- Prior art keywords
- refining
- natural resins
- resins
- recent natural
- condensation products
- 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
- 239000000025 natural resin Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- 238000007670 refining Methods 0.000 title claims description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 18
- 239000007859 condensation product Substances 0.000 claims description 7
- 150000002989 phenols Chemical class 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- -1 phenol alcohols Chemical class 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 4
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 4
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 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 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
- MLKXDPUZXIRXEP-UHFFFAOYSA-N 2-[6-fluoro-2-methyl-3-[(4-methylsulfinylphenyl)methylidene]-1-indenyl]acetic acid Chemical class CC1=C(CC(O)=O)C2=CC(F)=CC=C2C1=CC1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 241000016649 Copaifera officinalis Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 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
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Description
Verfahren zur Veredelung rezenter Naturharze Das Patent 440 003 hat zum Gegenstand ein Verfahren zur Veredelung rezenter Naturharze durch Vereinigung derartiger Harze mit Phenolharzen und Neutralisation der noch freien Harzsäuren in irgendeiner an sich bekannten Weise. Als Phenolharze sind in der Beschreibung nur Harze aus Phenol und dessen Homologen und Formaldehyd oder einem Formaldehyd abspaltenden Mittel erwähnt. Die Erfinderin hat ferner vorgeschlagen, statt dessen Kondensationsprodukte zu verwenden, die aus Phenolen und anderen Aldehyden als Formaldehyd bzw. aus Phenolen und Ketonen oder schließlich aus gemischten Kondensationsprodukten aus Phenolen mit Ketonen und Aldehyden hergestellt sind.Process for refining recent natural resins The patent 440 003 has the subject of a process for the refinement of recent natural resins by association such resins with phenolic resins and neutralization of the still free resin acids in some known way. As phenolic resins are in the description only resins made from phenol and its homologues and formaldehyde or a formaldehyde splitting agents mentioned. The inventor has also proposed instead Use condensation products made from phenols and aldehydes other than formaldehyde or from phenols and ketones or finally from mixed condensation products are made from phenols with ketones and aldehydes.
Es wurde nun gefunden, daß man an Stelle der bereits harzartigen Kondensationsprodukte auch kristallinische oder ölige Phenolalkohole oder deren Gemische verwenden kann, wie sie nach dem in der amerikanischen Patentschrift 1 614 171 beschriebenen Verfahren aus in Lösung gebrachten Phenolen init überschüssigen aliphatischen Aldehyden bei niedriger Temperatur erhalten werden. Diese Kondensationsprodukte eignen sich besonders für den angegebenen Zwcck, weil die Phenolalkohole und besonders die Phenol-Polyalkoholgemische nur sehr schwer beim Erwärmen anbrennen und sich infolgedessen licht mit dem Naturharz verschmelzen lassen; sodann sind die entstehenden Endprodukte wider Erwarten bedeutend leichter in Benzin und Leinöl löslich als die entsprechenden mit Kresolharzen hergestellten Harzprodukte, auch wenn man in beiden Fällen von im übrigen gleichen Gewichtsmengen Kresol und Formaldehyd ausgegangen ist. Die Darstellungsweise der neuen Produkte deckt sich im übrigen vollständig mit der im Patent 440 003 beschriebenen. Beispiel i ioo Teile Kolophonium werden mit io Teilen p-Kresoldialkohol zunächst i o Stunden auf 8o bis 9o°, sodann langsam ansteigend bis i 5o' erhitzt. Dabei steigt der Schmelzpunkt des Gemisches von 6o bis 70° langsam * auf i oo bis i i o°. Das erhaltene Produkt ist in Spiritus und Benzol löslich, in Benzin nur in der Wärme. Es wird dann in. bekannter Weise mit Glycerin, Glykol o. dgl. verestert, oder die noch vorhandenen Säurereste werden in anderer Weise abgesättigt. Beispiel 2 i Gramm-Molekül kristallisierte Carbolsäure wird mit der eben nötigen Menge einer etwa ioprozentigen Natronlauge gelöst und zu 6 Gramm-Molekülen wäßrigen Formaldehyds (3oprozentig) auf einmal hinzugegeben. Man läßt bei Zimmertemperatur 5 bis i o Tage stehen und fällt dann mit einer schwachen Säure, wie z. B. Kohlensäure, Essigsäure, Ameisensäure o. dgl., gegebenenfalls unter Zusatz von Wasser, aus. Da das entstandene Kondensationsprodukt weitgehend iln. Wassez löslich ist, empfiehlt es sich, die Flüssigkeit vor oder nach dem Ansäuern. bei gewöhnlichem Druck oder im Vakuum einzudampfen und das Ausscheiden des Öles durch Zusatz von Kochsalz zu beschleunigen und vollständiger zu gestalten..It has now been found that instead of the already resinous condensation products can also use crystalline or oily phenolic alcohols or mixtures thereof, as described in US Pat. No. 1,614,171 from dissolved phenols with excess aliphatic aldehydes low temperature can be obtained. These condensation products are particularly suitable for the stated purpose, because the phenol alcohols and especially the phenol-polyalcohol mixtures very difficult to burn when heated and as a result light up with the natural resin merge; then, contrary to expectations, the resulting end products are significant more easily soluble in gasoline and linseed oil than the corresponding ones made with cresol resins Resin products, even if in both cases they are otherwise of the same weight Run out of cresol and formaldehyde. How the new products are presented coincides completely with that described in patent 440,003. example 100 parts of rosin are mixed with 10 parts of p-cresol dialcohol for an initial 10 hours heated to 80 to 90 °, then slowly increasing to 15o '. The melting point rises of the mixture from 6o to 70 ° slowly * to i oo to i i o °. The product obtained is soluble in alcohol and benzene, in gasoline only when heated. It will then be in. In a known manner, esterified with glycerine, glycol or the like, or those that are still present Acid residues are saturated in a different way. Example 2 1 gram molecule crystallized Carbolic acid is mixed with the necessary amount of about 10 percent sodium hydroxide solution dissolved and into 6 gram molecules of aqueous formaldehyde (3 percent) added all at once. It is left to stand at room temperature for 5 to 10 days and then falls with a weak acid such as B. carbonic acid, acetic acid, formic acid or the like, optionally with the addition of water. Because the resulting condensation product largely iln. Wassez is soluble, it is recommended that the liquid before or after acidification. to evaporate at ordinary pressure or in a vacuum and the excretion to accelerate and make the oil more complete by adding table salt.
ioo Teile des so erhaltenen Produktes werden sofort mit 6oo Teilen Kolophonium, verschmolzen. Man erhitzt erst einige Stunden auf ioo bis -i2o°, dann mehrere Stunden auf 18o°, schließlich einige Zeit auf Zoo bis 25o°. Wenn der Schmelzpunkt nicht mehr- steigt und die Schaumbildung aufhört, ist die Reaktion beendet. Es wird dann in der üblichen. Weise, wie im Hauptpatent angegeben, verestert.100 parts of the product thus obtained are immediately mixed with 600 parts Rosin, fused. It is first heated to 100 to -i2o ° for a few hours, then several hours at 18o °, finally some time at the zoo up to 25o °. When the melting point no longer rises and foaming stops, the reaction is over. It will then in the usual. Way, as stated in the main patent, esterified.
Die Mengenverhältnisse sind ganz nach Belieben varüerbar; j e nachdem, ob man mehr oder weniger Kolophonium oder statt Kolophonium andere saure Naturharze zusetzt, :erhält man Produkte, die sich ia ihren Eigenschaften mehr dem Kolophonium oder den Kopalen oder überhaupt den hochwertigen Naturharzen nähern.The proportions can be varied at will; depending on, whether you use more or less rosin or other acidic natural resins instead of rosin adds: one obtains products that are more like colophony in terms of their properties or the copals or the high-quality natural resins in general.
Man kann das ganze Verfahren unter gewöhnlichem oder erhöhtem Druck, im Autoklaven oder ün Vakuum, an der Luft oder in Gegenwart indifferenter Gase ausführen und kann unter Anwendung aller Vorsichtsmaßregeln leicht zu sehr hellen und trotzdem hochschmelzenden Harzen gelangen.The whole procedure can be carried out under normal or increased pressure, in an autoclave or in a vacuum, in air or in the presence of inert gases and, with all precautionary measures, can easily become very bright and yet high-melting resins.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEC33190D DE474787C (en) | 1923-02-15 | 1923-02-15 | Process for refining recent natural resins |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEC33190D DE474787C (en) | 1923-02-15 | 1923-02-15 | Process for refining recent natural resins |
Publications (1)
Publication Number | Publication Date |
---|---|
DE474787C true DE474787C (en) | 1929-04-12 |
Family
ID=7020699
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEC33190D Expired DE474787C (en) | 1923-02-15 | 1923-02-15 | Process for refining recent natural resins |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE474787C (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE747788C (en) * | 1938-11-05 | 1944-10-16 | Process for the production of lightfast condensation resins |
-
1923
- 1923-02-15 DE DEC33190D patent/DE474787C/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE747788C (en) * | 1938-11-05 | 1944-10-16 | Process for the production of lightfast condensation resins |
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