DE735498C - Process for the production of synthetic resins - Google Patents

Process for the production of synthetic resins

Info

Publication number
DE735498C
DE735498C DEL99206D DEL0099206D DE735498C DE 735498 C DE735498 C DE 735498C DE L99206 D DEL99206 D DE L99206D DE L0099206 D DEL0099206 D DE L0099206D DE 735498 C DE735498 C DE 735498C
Authority
DE
Germany
Prior art keywords
synthetic resins
parts
production
acid
resin
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
Application number
DEL99206D
Other languages
German (de)
Inventor
Alelio Gaetano F D
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
AEG AG
Original Assignee
AEG AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by AEG AG filed Critical AEG AG
Application granted granted Critical
Publication of DE735498C publication Critical patent/DE735498C/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/06Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
    • C08G63/065Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids the hydroxy and carboxylic ester groups being bound to aromatic rings
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/06Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
    • C08G63/08Lactones or lactides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Herstellung von Kunstharzen Die Erfindung betrifft Kunstharze, die aus Cyclohexanol oder seinen Abkömmlingen und Oxybenzoesäure in Gegenwart geringer Mengen von Katalysatoren, wie z. B. Sch-,vefelsäure, erhalten werden. Es ist überraschend, daß aus diesen Komponenten Kunstharze gewinnbar sind, nachdem Cyclohexanol bei Behandlung mit Schwefelsäure lediglich zu Cyclohexan dehydriert wird, unter Bildung von ganz ,geringen Harzmengen, und bei Ersatz der Oxyb:enzoesäure durch Phenol oder Kresol bei Anwesenheit von - Schwefelsäure nur Cyclohexylphenol oder -kresol gebildet wird.Process for the production of synthetic resins The invention relates to synthetic resins, those from cyclohexanol or its derivatives and oxybenzoic acid in the presence of less Amounts of catalysts, such as. B. Sch, vefelsäure can be obtained. It is surprising that synthetic resins can be obtained from these components after treatment with cyclohexanol is only dehydrated with sulfuric acid to cyclohexane, with the formation of whole , small amounts of resin, and when the oxyb: enzoic acid is replaced by phenol or cresol in the presence of sulfuric acid, only cyclohexylphenol or cresol is formed.

Es ist zwar schon bekannt, Cyclohexanol und Salicylsäure ohne Katalysatoren zur Herstellung von Kunstharzläsungsmitteln zu verestern. Die Kondensation in Gegenwart von Katalysatoren gemäß der Erfindung zwecks Herstellung hitzehärtbarer Kunstharze ist dagegen aus den bekannten Vorschriften nicht zu entnehmen. Beispiel z Ein Gemisch aus 2o Gewichtsteilen p-Oxybenzoesäure, ¢3,5 Gewichtsteilen Cyclohexanol, i i-Gewichtsteilen Toluol und o,2 Gewichts-. teilen 96o;oiger Schwefelsäure wird am Rückflußkühler 13 Stunden erhitzt. Die erhaltene flüssige Menge wird bei Atmosphärendruck bis auf 155° erwärmt, wobei 1q.,8Teile Destillat übergehen. Der Rückstand wird im Vakuum bis zur gewünschten Gelkonsistenzeingedampft. Beispiel 2 Dieselben Mengen derselben Ausgangsstoffe wie in Beispiel i werden 15 Stundieh am Rückfußkübler erwärmt. Die erhaltene Masse wird dreimal mit dem gleichen Volum-Wasser unter Zusatz von etwas Äthyläther ausgewas.r-hon, die ausgewaschene -'#ther-Harz-Lösung wird zur Entfernung von Wasser mit fester Soda ausgeschüttet, filtriert und anschließend der Äther bei Atmösphärendruck, das Toluol und andere leicht siedende Bestandteile im Vakuum abdestilliert. Bei höchstens 157' (2o bis 22 mm Quecksilberdruck) wird die D,-stillation abgebrochen. Es fällt ein rotbraunes Harz an, das bei Zimmertemperatur hart und zäh ist.Although it is already known, cyclohexanol and salicylic acid without catalysts to esterify for the manufacture of synthetic resin solvents. The condensation in the present of catalysts according to the invention for the purpose of producing thermosetting synthetic resins on the other hand, cannot be found in the known regulations. Example z A mixture from 20 parts by weight of p-oxybenzoic acid, 3.5 parts by weight of cyclohexanol, i i parts by weight Toluene and 0.2% by weight. divide 96o; oiger sulfuric acid in the reflux condenser Heated for 13 hours. The liquid amount obtained becomes up to at atmospheric pressure 155 ° heated, with 1q., 8 parts of distillate pass over. The residue is in vacuo evaporated to the desired gel consistency. Example 2 The same Quantities of the same starting materials as in Example i are used for 15 hours on the rear-foot tub warmed up. The resulting mass is three times with the same volume of water with the addition washed out by a little ethyl ether, the washed-out - '# ether-resin solution becomes poured out to remove water with solid soda, filtered and then the ether at atmospheric pressure, the toluene and other low-boiling components distilled off in vacuo. At 157 'or less (2o to 22 mm of mercury pressure) the D, distillation canceled. A red-brown resin is obtained, which at room temperature is hard and tough.

. Beispiel 3 2o Teil,. p-Oxybenzoesäure, 23 Teile Cyclo-'hexanol und o,2Teile 96@!oige Schwefelsäure werden 71 Stunden am Rückflußkühler gekocht. Die erhaltene Harzmenge wird bis zur Neutralität mit verdünnter Sodalösung und dann mit Wasser gewaschen, in Toluol aufgenommen, mit Kohle entfärbt und dann das Toluol abgedampft. Es hinterbleibt ein viscoses rötliches Harz, dessen Viscosität und Erweichungspunkt mit steigender Erhitzungstemperatur ansteigt.. Example 3 2o part. p-oxybenzoic acid, 23 parts of cyclo-'hexanol and 0.2 parts of 96% sulfuric acid are refluxed for 71 hours. the amount of resin obtained is until neutrality with dilute soda solution and then washed with water, taken up in toluene, decolorized with charcoal and then the toluene evaporated. What remains is a viscous reddish resin, its viscosity and softening point increases with increasing heating temperature.

Beispiel q. .Example q. .

21 Gewichtst°ile o-Oxybenzoesäure (Salicylsäure), 21"q. Gewichtsteile Cyclohexanol und o,4 Gewichtsteile 96o!oiger Schwefelsäure werden 2 Stunden am Rückflufikühler erwärmt. Nach dem Abkühlen werden zur Aufnahme der Schwefelsäure 3o Teile warmes Wasser zugegeben, darauf das Harz mit Äthyläther ausgeschüttelt und die Ätherlösung vom Wasser getrennt. Der Äther wird bei Atmosphärendruck abdestilliert. Nach einer Vakuumdestillation wird eine teerige Harzmasse erhalten.21 parts by weight of o-oxybenzoic acid (salicylic acid), 21 "q. Parts by weight Cyclohexanol and 0.4 parts by weight of 96% sulfuric acid are refluxed for 2 hours warmed up. After cooling, 3o parts are warm to absorb the sulfuric acid Water added, then the resin shaken out with ethyl ether and the ethereal solution separated from the water. The ether is distilled off at atmospheric pressure. After a A tarry resin mass is obtained by vacuum distillation.

Die gemäß der Erfindung hergestellten Harze sind in Alkohol, Aceton, Benzol, Mischungen aus Aceton und Benzol, Toluol, kylol und anderen Lösungsmitteln löslich. Sie sind weich und klebrig bis hart und brüchig. Bei längerer Erhitzung auf höhere Temperaturen, von z. B. i5o--, gehen sie in den unlöslichen Zustand über. Sie können zur Herstellung von Lacken, als Bindemittel für Fasern oder Gewebe aus Papier, Batunwolle, Seide, Asbest, Glasgespinst u. dgl., zur Modifizierung bekannter Kunstharze und für andere Zwecke verwendet werden.The resins prepared according to the invention are in alcohol, acetone, Benzene, mixtures of acetone and benzene, toluene, kylene and other solvents soluble. They are soft and sticky to hard and brittle. With prolonged heating to higher temperatures, from z. B. i5o--, they pass into the insoluble state. They can be used in the manufacture of paints, as binders for fibers or fabrics Paper, batun wool, silk, asbestos, fiberglass and the like, known for modification Synthetic resins and used for other purposes.

An Stelle des Cyclohexanols können Abkömmlinge dieses Stoffes, wie z. B. die Alkylcyclohexanole, und an Stelle der Oxybenzoesäure deren Abkömmlinge, wie z. B. Dioxybenzoesäure, verwendet werden.Instead of cyclohexanol, derivatives of this substance, such as z. B. the alkylcyclohexanols, and instead of oxybenzoic acid their derivatives, such as B. dioxybenzoic acid can be used.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Kunst-. harzen aus Oxybenzoesäure und Cyclohexanol, dadurch gekennzeichnet, daß die beiden Komponenten in Gegenwart von Katalysatoren kondensiert werden.PATENT CLAIM: Process for the production of art. resins made from oxybenzoic acid and cyclohexanol, characterized in that the two components are in the presence be condensed by catalysts.
DEL99206D 1938-10-07 1939-10-08 Process for the production of synthetic resins Expired DE735498C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US735498XA 1938-10-07 1938-10-07

Publications (1)

Publication Number Publication Date
DE735498C true DE735498C (en) 1943-05-15

Family

ID=22114365

Family Applications (1)

Application Number Title Priority Date Filing Date
DEL99206D Expired DE735498C (en) 1938-10-07 1939-10-08 Process for the production of synthetic resins

Country Status (1)

Country Link
DE (1) DE735498C (en)

Similar Documents

Publication Publication Date Title
DE524189C (en) Process for the production of polymerization products from vinyl ethers
DE534214C (en) Process for the production of synthetic resin from polyhydric alcohols and polybasic acids or their anhydrides
DE735498C (en) Process for the production of synthetic resins
DE1021858B (en) Process for the preparation of aromatic oxacyclobutane derivatives
AT147482B (en) Process for the production of malleable and hardenable condensation products and of synthetic masses from them.
DE339107C (en) Process for the preparation of synthetic resin
DE364042C (en) Process for the preparation of condensation products from ethylene glycol monoaryl ethers
DE575750C (en) Process for the production of polyglycides
DE1770816A1 (en) Process for the production of flexible phenolic resins
DE1002489B (en) Adhesive based on natural and synthetic rubber mixed with high-melting, soluble phenolic resins
DE364044C (en) Process for the preparation of resinous condensation products from phenols and formaldehyde
DE529323C (en) Process for the production of a viscous condensation product from phenol and formaldehyde
DE396510C (en) Process for the production of resinous condensation products from phenols and formaldehyde
DE859952C (en) Process for the production of synthetic resins
DE360415C (en) Process for the preparation of alkyl ethers of starch, dextrin and similar carbohydrates
DE673962C (en) Process for the manufacture of drying ointments
DE953743C (en) Thermoplastic mass
DE540071C (en) Process for the production of plastics which contain urea and / or thiourea-formaldehyde condensation products
DE712002C (en) Process for the production of alkyd resins
DE918835C (en) Process for the production of resinous condensation products
US1102632A (en) Enamel lacquer or varnish composition.
DE841592C (en) Process for the preparation of 3-oxytetrahydrofurans
DE358399C (en) Process for the preparation of resinous condensation products from phenol alkyl ethers and formaldehyde
AT131131B (en) Process for the preparation of curable condensation products from phenolic alcohols.
AT201860B (en) Process for the production of synthetic resins containing aluminum