DE554668C - Process for the production of condensation products - Google Patents
Process for the production of condensation productsInfo
- Publication number
- DE554668C DE554668C DEI41383D DEI0041383D DE554668C DE 554668 C DE554668 C DE 554668C DE I41383 D DEI41383 D DE I41383D DE I0041383 D DEI0041383 D DE I0041383D DE 554668 C DE554668 C DE 554668C
- Authority
- DE
- Germany
- Prior art keywords
- production
- condensation products
- parts
- products
- acetone
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000007859 condensation product Substances 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- -1 alkyl vinyl ketones Chemical class 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- LABTWGUMFABVFG-UHFFFAOYSA-N methyl propenyl ketone Chemical compound CC=CC(C)=O LABTWGUMFABVFG-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920005735 poly(methyl vinyl ketone) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/28—Condensation with aldehydes or ketones
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
Verfahren zur Herstellung von Kondensationsprodükten Es ist schon vorgeschlagen worden, Polyvinylverbindungen, z. B. Polyvinylacetat oder Polyvinylalkohole, mit Aldehyden zu kondensieren, wobei Produkte, die als Kunstmassen verwendet werden können, erhalten werden.Process for the production of condensation products It is nice it has been proposed to use polyvinyl compounds, e.g. B. polyvinyl acetate or polyvinyl alcohols, to condense with aldehydes, whereby products that are used as artificial masses can be obtained.
Es wurde nun gefunden, daß man ebenfalls als Kunstmassen verwendbare Produkte erhält, wenn man polymere Alkylvinylketone, z. B. Polymethylvinylketon, Polyäthylvinylketon usw., in Gegenwart von sauer reagierenden Substanzen, wie Mineralsäuren oder sauren Salzen, mit Aldehyden umsetzt.It has now been found that they can also be used as art masses Products obtained when polymeric alkyl vinyl ketones, e.g. B. polymethyl vinyl ketone, Polyethylvinylketone, etc., in the presence of acidic substances such as mineral acids or acid salts, reacts with aldehydes.
Zur Umsetzung mit den polymeren Alkylvinylketonen geeignete Aldehyde sind z. B. Formaldehyd und seine Polymeren, Acetaldehyd, Propionaldehyd, Crotonaldehyd, Benzaldehyd usw.Aldehydes suitable for reaction with the polymeric alkyl vinyl ketones are z. B. Formaldehyde and its polymers, acetaldehyde, propionaldehyde, crotonaldehyde, Benzaldehyde, etc.
Bei der Umsetzung kann man auch in Gegenwart von Lösungsmitteln, z. B. Wasser, Eisessig, Aceton usw., arbeiten. In manchen Fällen läßt sich die Umsetzung durch Erhitzen unter Druck stark beschleunigen.In the implementation you can also in the presence of solvents, for. B. water, glacial acetic acid, acetone, etc., work. In some cases it can be implemented accelerate strongly by heating under pressure.
Führt man die Umsetzung in Abwesenheit von Katalysatoren und bei höheren Temperaturen durch, so erhält man im allgemeinen zähe, elastische und in organischen Lösungsmitteln unlösliche Produkte. Arbeitet man dagegen in Gegenwart größerer Mengen von Mineralsäuren in der Kälte, so werden in der Regel weiße, flockige Pulver erhalten, die in organischen Lösungsmitteln, wie Chloroform, Methylenchlorid, Dioxan, Benzolalkoholgemischen u. dgl., löslich sind. Derartige Lösungen lassen sich zur Herstellung von Lacken, Imprägnierungen usw. verwenden und können auch in der üblichen Weise zur Herstellung von Fäden oder Filmen verwendet werden.If the reaction is carried out in the absence of catalysts and at higher rates Temperatures through, one obtains in general tough, elastic and organic Solvent-insoluble products. If, on the other hand, you work in the presence of larger quantities of mineral acids in the cold, white, flaky powders are usually obtained, those in organic solvents such as chloroform, methylene chloride, dioxane, benzene alcohol mixtures and the like, are soluble. Such solutions can be used for the production of paints, Use impregnations etc. and can also be used in the usual way for production of threads or films.
Durch Anwendung von Hitze und Druck werden die erhaltenen Umsetzungsprodukte plastisch, und sie lassen sich daher gut zu Preßmassen verarbeiten. Die Eigenschaften der Produkte können durch Zugabe von Weichmachungsmitteln, Farb- und Füllstoffen usw. in weiten Grenzen variiert werden. Die farblosen Produkte können beispielsweise bei der Herstellung von splitterfreiem Glas als Zwischenschichten zwischen den Glasplatten verwendet werden.The reaction products obtained are obtained by applying heat and pressure plastic, and they can therefore be easily processed into molding compounds. The properties the products can be made by adding plasticizers, dyes and fillers etc. can be varied within wide limits. The colorless products can, for example in the production of shatterproof glass as intermediate layers between the glass plates be used.
Beispiel i ioo Teile polymeres Methylvinylketon werden in 9,ooo Teilen Aceton gelöst, mit 5o Teilen 4o°/oigem Formaldehyd und io Teilen konzentrierter Salzsäure versetzt und 5 Stunden lang zum Sieden erhitzt. Nach dem Verjagen des Lösungsmittels hinterbleibt ein gelb gefärbtes, zähes Harz, das in Aceton quellbar ist und sich in der Hitze zu Formstücken verpressen läßt. Beispiel 2 6o Teile; polymeres Methylvinylmethylketon werden in 8oo Teilen Aceton gelöst und nach Zusatz von 3o Teilen 4o°/oigem Formaldehyd und 1,5 Teilen konzentrierter Salzsäure eine Zeitlang unter Rückflußkühlung zum Sieden erhitzt. Sobald die Umsetzung beendet ist, wird das Aceton abdestilliert und das entstandene Produkt mit Wasser ausgewaschen. Die erhaltene dunkel gefärbte Masse läßt sich gut auf Preßmassen verarbeiten.Example 100 parts of polymeric methyl vinyl ketone are divided into 9,000 parts Dissolved acetone, with 50 parts of 40% formaldehyde and 10 parts more concentrated Hydrochloric acid is added and the mixture is heated to boiling for 5 hours. After chasing away the The solvent leaves a yellow, viscous resin that swells in acetone and can be pressed into molded pieces in the heat. example 2 6o parts; polymeric methyl vinyl methyl ketone are dissolved in 800 parts of acetone and after adding 3o parts 40% formaldehyde and 1.5 parts more concentrated Hydrochloric acid heated to boiling for a while under reflux cooling. Once the implementation is complete, the acetone is distilled off and the resulting product with water washed out. The dark colored mass obtained can be easily processed on molding compounds.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI41383D DE554668C (en) | 1930-10-05 | 1930-10-05 | Process for the production of condensation products |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI41383D DE554668C (en) | 1930-10-05 | 1930-10-05 | Process for the production of condensation products |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE554668C true DE554668C (en) | 1932-07-13 |
Family
ID=7190537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI41383D Expired DE554668C (en) | 1930-10-05 | 1930-10-05 | Process for the production of condensation products |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE554668C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE892244C (en) * | 1942-01-28 | 1953-10-05 | Rheinpreussen Ag | Process for the production of easily soluble fusible synthetic resins |
| US3159603A (en) * | 1960-03-17 | 1964-12-01 | Ibm | Catalytic condensation of polymers of alpha-alkenyl ketones |
-
1930
- 1930-10-05 DE DEI41383D patent/DE554668C/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE892244C (en) * | 1942-01-28 | 1953-10-05 | Rheinpreussen Ag | Process for the production of easily soluble fusible synthetic resins |
| US3159603A (en) * | 1960-03-17 | 1964-12-01 | Ibm | Catalytic condensation of polymers of alpha-alkenyl ketones |
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