DE305575C - - Google Patents
Info
- Publication number
- DE305575C DE305575C DENDAT305575D DE305575DA DE305575C DE 305575 C DE305575 C DE 305575C DE NDAT305575 D DENDAT305575 D DE NDAT305575D DE 305575D A DE305575D A DE 305575DA DE 305575 C DE305575 C DE 305575C
- Authority
- DE
- Germany
- Prior art keywords
- formaldehyde
- products
- naphthalene
- oil
- parts
- 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.)
- Active
Links
- 239000002253 acid Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 239000007859 condensation product Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims 1
- CBYZIWCZNMOEAV-UHFFFAOYSA-N formaldehyde;naphthalene Chemical class O=C.C1=CC=CC2=CC=CC=C21 CBYZIWCZNMOEAV-UHFFFAOYSA-N 0.000 claims 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N Tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000001293 FEMA 3089 Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000002790 naphthalenes Chemical class 0.000 description 3
- 239000012262 resinous product Substances 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N Chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N Dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 241000779819 Syncarpia glomulifera Species 0.000 description 1
- 229940036248 Turpentine Drugs 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 230000000996 additive Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring 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
- C08G10/00—Condensation polymers of aldehydes or ketones with aromatic hydrocarbons or halogenated aromatic hydrocarbons only
- C08G10/02—Condensation polymers of aldehydes or ketones with aromatic hydrocarbons or halogenated aromatic hydrocarbons only of aldehydes
Landscapes
- 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
Läßt man auf ein hydriertes Naphthalin, z. B. Tetrahydronaphthalin, bei Gegenwart von Säuren Formaldehyd oder Formaldehyd entwickelnde Substanzen einwirken, so erhält man neue Kondensationsprodukte, welche mit bestem Erfolge als künstliches Harz Verwendung finden können. Die neuen Produkte sind schwer löslich in Alkohol und Äther, leicht löslich in Benzol, Chlorbenzol, Chloroform usw. Sie lassenIf one leaves on a hydrogenated naphthalene, z. B. tetrahydronaphthalene, in the presence of Acids, formaldehyde or formaldehyde-evolving substances are obtained new condensation products, which are used with great success as artificial resin can. The new products are sparingly soluble in alcohol and ether, easily soluble in benzene, Chlorobenzene, chloroform, etc. You leave
ίο sich sehr gut zusammen mit Terpentinöl, Leinöl usw. verarbeiten und eignen sich insbesondere zur Herstellung von Öllacken, wobei sowohl Terpentinöl wie auch Terpentinölersatz Verwendung finden ■können. ■ Desgleichen- kann man sie zur Herstellung von Fußbodenlacken benutzen, die.eine gewisse Härte besitzen sollen, ferner auch zur Erzeugung von Mattlacken, die auf terpentinölartiger Grundlage unter Zusatz von Äther hergestellt werden. Auch als Zusatz-ίο goes very well with turpentine oil, linseed oil etc. process and are particularly suitable for the production of oil paints, with both Oil of turpentine as well as oil substitute ■ can be used. ■ Likewise- can they are used to produce floor varnishes that should have a certain hardness, also for the production of matt lacquers, which are based on turpentine oil with additives produced by ether. Also as an additional
verdickungsmittel für fette halbtrocknende Öle, ferner für Firnisse und billigere Rotationsdruckfarben kann man die neuen Harze verwenden. Endlich kommen sie auch als Zusatz für Momentlederschwärze in Frage, wobei teils größere Deckkraft erzielt,, teils die Reibechtheit erhöht werden soll. ... ■The new resins can be used for thickening semi-drying oils, varnishes and cheaper rotary printing inks. Finally, they can also be used as an additive for momentary leather black, although in some cases greater opacity achieved, partly the rubbing fastness should be increased. ... ■
In ein Gemisch von 250 Teilen Tetrahydronaphthalin mit 165 Teilen Formaldehydlösung 3Oprozentig läßt man bei etwa 40° 250 Teile Schwefelsäure 66° Βέ im Verlaufe mehrerer Stunden unter Rühren einlaufen. Hierauf wird auf 80 bis ioo° erhitzt, bis die Masse in einen zähen Teig verwandelt ist. Dieser kann z. B.In a mixture of 250 parts of tetrahydronaphthalene with 165 parts of formaldehyde solution 30 percent is left at about 40 ° 250 parts Sulfuric acid 66 ° Βέ pour in over the course of several hours while stirring. Then will Heated to 80 to 100 ° until the mixture has turned into a tough dough. This can e.g. B.
durch Waschen mit heißem Wasser, evtl. unter Zusatz von Soda, von der überschüssigen Säure befreit werden. Man erhält so ein gelbliches, feines Pulver, das man durch^ Schmelzen und Erhitzen auf 120 bis 200 ° völlig vom Wasser befreien kann. "Nach dem Erstarren erhält man eine springharte, harzartige Masse.by washing with hot water, possibly with the addition of soda, from the excess acid to be freed. In this way a yellowish, fine powder is obtained which can be melted and melted Heating to 120 to 200 ° can completely remove the water. "After solidifying, you get a hard, resinous mass.
In eine Lösung von 100 Teilen Tetrahydro- +5 naphthalin und 60 Teilen Methylal in 50O1TdIeIa Chloroform läßt man 200 Teile Schwefelsäure 66° Be bei 40° zufließen. Man steigert hierauf, die Temperatur während mehrerer Stunden auf 50 bis 60 ° und erhält nach dem Abblassen des Chloroforms mittels Wasserdampfes und Neutralwaschen eine Masse von ganz ähnlichen Eigenschaften wie bei Beispiel 1.200 parts of sulfuric acid 66 ° Be at 40 ° are allowed to flow into a solution of 100 parts of tetrahydro- +5 naphthalene and 60 parts of methylal in 50O 1 TdIeIa chloroform. The temperature is then increased to 50 to 60 ° for several hours and, after the chloroform has been blown off by means of steam and neutral washing, a mass with properties very similar to those of Example 1 is obtained.
An Stelle, von Schwefelsäure lassen sich auch andere Säuren oder saure Kondensationsmittel verwenden.Instead of sulfuric acid, other acids or acidic condensing agents can also be used use.
Aus der Patentschrift 207743 ist bekannt, daß man durch Kondensation von Naphthalin mit Farmoldehyd innerhalb sehr enger Grenzen zu harzartigen Produkten gelangen kann. 60 · Hier wird also Naphthalin selbst im Gegensatz zu hydrierten Naphthalinen bei der vorliegenden Erfindung als^ Ausgangsmaterial verwendet; da es aber'bekannt ist, daß der Charakter des Naphthalins durch die Hydrierung ganz wesentlieh geändert wird, indem, solche Hydrierungsprodukte sich nicht mehr wie einfache Naphthalinderivate, sondern wie. homologe. Benzolderivate-verhalten (vgl. z. B. Richter, Organische Chemie, 11. Aufl., II. Bd., S. 653 und die dort näher bezeichnete Literaturstelle), so war der Erfolg des vorliegenden Verfahrens nichtFrom the patent specification 207743 it is known that by condensation of naphthalene with farmoldehyd can reach resinous products within very narrow limits. 60 · So here is naphthalene itself in contrast to hydrogenated naphthalenes in the present Invention used as starting material; but since it is known that the character of the naphthalene owing to the hydrogenation is essential is changed in that such hydrogenation products are no longer like simple naphthalene derivatives, but how. homologous. Benzene derivative behavior (see e.g. Richter, Organische Chemie, 11th edition, II. Vol., P. 653 and the literature specified there), see above the success of the present proceedings was not
vorauszusehen. Dazu kommt noch, daß man nach den Angaben dieses Patentes ein Harz erhält, das in Terpentinöl, Leinöl, Firnis usw. unlöslich?is,t .jucÄ denizufplge zur Bereitung von Lacken' nicht'1 verWeridfet "werden kann. Die, nach der vo^ge^^i),.,p):ßnäuj3g';:.. erhältlichen Harze sind dagegen in derartigen Lösungsmitteln sehr leicht löslich und lassen sich, wie oben bereits ausgeführt, in der verschiedenartigsten Weise mit Nutzen verwenden.to foresee. In addition, according to the information in this patent, a resin is obtained that is insoluble in turpentine oil, linseed oil, varnish, etc. ? can be "is, .jucÄ t denizufplge for the preparation of lacquers' not '1 verWeridfet The after vo ^ ge ^^ i), p): ßnäuj3g';:.. .. available resins, however, are very in such solvents Easily soluble and, as already stated above, can be used with benefit in the most varied of ways.
Was sodann die Patentschrift 263159 betrifft, so sollen hier hydrierte Verbindungen nach Art des Dihydrobenzols durch Einwirkung von Kondensationsmitteln, jedoch ohne Witwirkung von Formaldehyd, in harzartige Produkte übergeführt werden. Es ist ohne weiters klar, daß diese Produkte in ihrem Aufbau vollständig verschieden sein müssen von den harzartigen Stoffen, die gemäß vorliegender Erfindung zu erhalten sind. Auch zeigt ein Versuch, Tetrahydronaphthalin gemäß Patentschrift 263159 ohne Gegenwart von Formaldehyd zu kondensieren, daß keine harzartigen Produkte entstehen. Ferner ist noch darauf hinzuweisen, daß Dihydrobenzol und seine Homologen, Derivate usw. im Gegensatz zum Tetrahydronaphthalin technisch nur schwer zugänglich sind. . ■As regards patent specification 263159, hydrogenated compounds according to Art of dihydrobenzene by the action of condensing agents, but without any effect formaldehyde, can be converted into resinous products. It is readily apparent that these products must be completely different in structure from the resinous ones Substances to be obtained according to the present invention. An experiment also shows tetrahydronaphthalene to condense according to patent specification 263159 without the presence of formaldehyde, that no resinous products arise. It should also be pointed out that dihydrobenzene and its homologues, In contrast to tetrahydronaphthalene, derivatives etc. are technically difficult to obtain are. . ■
Nach der englischen Patentschrift 4648/1911 endlich soll eine sehr große Zahl der verschiedenartigstenVerbindungen, in konzentrierter Schwefelsäure gelöst, mit Formaldehyd kondensiert werden zwecks Erzielung neuer Stoffe, die in Verbindung mit dem Formaldehydrest auch eine Schwefel, enthaltende Gruppe besitzen sollen. Diese Produkte sind also vollständig verschieden von denjenigen der vorliegenden Erfindung, welche keinen Schwefel enthalten; irgendein Hinweis auf den-Erfolg des vorliegenden Verfahrens ließ sich also diesem englischen Patent nicht entnehmen.According to the English patent specification 4648/1911 finally, a very large number of the most diverse compounds dissolved in concentrated sulfuric acid, condensed with formaldehyde for the purpose of obtaining new substances that are in Compound with the formaldehyde residue also have a sulfur-containing group should. So these products are completely different from those of the present Invention which do not contain sulfur; any indication of the success of the present The method could not be found in this English patent.
Claims (1)
Publications (1)
Publication Number | Publication Date |
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DE305575C true DE305575C (en) |
Family
ID=559070
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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Country Status (1)
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1024236B (en) * | 1953-06-26 | 1958-02-13 | Basf Ag | Process for the production of coating resins from naphthalene and formaldehyde |
US3036993A (en) * | 1958-03-18 | 1962-05-29 | Basf Ag | Synthetic resins soluble in ethanol and derived from tetrahydronaphthyl-hydroxyphenylethane and formaldehyde, and a process of producing same |
US3036994A (en) * | 1958-03-21 | 1962-05-29 | Basf Ag | Curable synthetic resin compositions from formaldehyde and phenolic compounds, and aprocess of curing same |
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0
- DE DENDAT305575D patent/DE305575C/de active Active
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1024236B (en) * | 1953-06-26 | 1958-02-13 | Basf Ag | Process for the production of coating resins from naphthalene and formaldehyde |
US3036993A (en) * | 1958-03-18 | 1962-05-29 | Basf Ag | Synthetic resins soluble in ethanol and derived from tetrahydronaphthyl-hydroxyphenylethane and formaldehyde, and a process of producing same |
US3036994A (en) * | 1958-03-21 | 1962-05-29 | Basf Ag | Curable synthetic resin compositions from formaldehyde and phenolic compounds, and aprocess of curing same |
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