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DE696287C - Process for the preparation of reaction products of divinylbenzene - Google Patents

Process for the preparation of reaction products of divinylbenzene

Info

Publication number
DE696287C
DE696287C DE1935I0052775 DEI0052775D DE696287C DE 696287 C DE696287 C DE 696287C DE 1935I0052775 DE1935I0052775 DE 1935I0052775 DE I0052775 D DEI0052775 D DE I0052775D DE 696287 C DE696287 C DE 696287C
Authority
DE
Germany
Prior art keywords
divinylbenzene
preparation
reaction products
styrene
aromatic
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
DE1935I0052775
Other languages
German (de)
Inventor
Dr Helmuth Meis
Dr Leo Rosenthal
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DE1935I0052775 priority Critical patent/DE696287C/en
Application granted granted Critical
Publication of DE696287C publication Critical patent/DE696287C/en
Expired legal-status Critical Current

Links

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
    • C08G8/30—Chemically modified polycondensates by unsaturated compounds, e.g. terpenes
    • 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
    • C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F12/34—Monomers containing two or more unsaturated aliphatic radicals
    • C08F12/36—Divinylbenzene
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/36—Polymerisation in solid state
    • 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
    • C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F212/02—Monomers containing only one unsaturated aliphatic radical
    • C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F212/06—Hydrocarbons
    • C08F212/08—Styrene

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Description

Verfahren zur Herstellung von Reaktionsprodukten des Divinylbenzols Gemäß Patent 674 984 werden neue Rei aktionsprodukte des Styrols. dadurch erhalten, daß man Gemische von Styrol und aromatischen Athern mit solchen sauer reagierenden oder siäureabspaltendem Substanzen biehandelt, welche Styrol zu polymerisieren ver. mögen.Process for the preparation of reaction products of divinylbenzene According to patent 674,984, new Rei are action products of styrene. obtained by that one mixes styrene and aromatic ethers with those reacting acidic or acid-releasing substances which polymerize styrene ver. to like.

Es wurde nun gefunden, -daß man Produkte von ähnlichen Eigenschaften erhält, wenn man bei dem. Verfahren des Hauptpatentes das Styrol durch Dzvinylbenzol ersetzt. Als Divinylb-enzole werden vorzugsweise die o- und die p-Verbändung - ;angewandt, wie sie bei der technischen Herstellung von Styrol anfallen (s. Ber. 67, S. i 164 ff). Die Reaktion kann in einem indifferenten Lösungsmittel, wie z. B. Tetrachlorkoh1enstoff, Benzin, Xylol o. dgl., ausgeführt werden. Als Beispiele für polymerisierend wirkende Substanzen seien Zinntetrachlorid, Aluminiumchlorid, Borfluoressigsäure genannt. Dier Katalysator kann nach beendeter Reaktion z. B. durch Auswaschen des R.eaktIonsigemisches mit Wasser oder durch Behandlung mit reaktionsfähigen Metalloxyden, wie z. B. Calciumoxyd, entfernt werden. Die Ääufig auftretende Wärmetönung wird gegebenenfalls durch Kühlung oder auch durch vorsichtige Zugabe des Katalysators geregelt. Als Beispiel für aromatische Äther seien Äther der Phenole, Kres Dole, Naphthole, Oxy-,diphenole usw. genannt. Wie dies: in Patent 695z78 für analoge Umsetzungen des Styrols. angegeben ist, sind aromatische Oxyverbindungeneiner ähnlichen Reaktion fähig, so. -daß auch in diesem Fall die aromatischen Äther teilweise durch aromatische Oxyver-Bindungen ersetzt werden können. Beispiel Ein Gemisch von 6o Gewichtsteilen D2-vinylbenzol, 77 Gewichtsteilen P-Naphtholäthyläther und 70 Gewichtsteilen Tetrachlorkohlenstoff wird mit 2 Gewichtsteilen Zinntetrachlorid versetzt und 12 Stunden bei einer 20° nicht übersteigenden Temperatur verrührt. Dias Reaktionsgemisch wird mit weiteren Mengen Tetrachlorkohlenstoff verdünnt und unter Zugabe von Calciurhoxyd und Bleicherde 3 Stunden auf' 8o° @erwärmt. Aus der filtrierten Lösung wird durch Destillation das Lösungsmittel und eine gie-' ringe Menge nicht umgesetzter (3--Vaphthoiäthyläther entfernt. Nach dem Entfernen der flüchtigen Bestandteile ,durch Destillation imt. Vakuum erhält man rao Gewichtsteile ein; hellgelben Harzes, das in trocknenden ölen;-, in aliphatischen und .aromatischen Kohlei=' wassersto,ffen, wie sie in der Lacktechnik ge= braucht werden, löslich ist. It has now been found that one obtains products of similar properties if one in the. Process of the main patent which replaces styrene with vinylbenzene. As divinylbenzenes, the o- and p-compounds are preferably used, such as are obtained in the industrial production of styrene (see Ber. 67, pp. I 164 ff). The reaction can be carried out in an inert solvent, such as. B. carbon tetrachloride, gasoline, xylene o. Examples of substances with a polymerizing effect are tin tetrachloride, aluminum chloride, and borofluoroacetic acid. The catalyst can after completion of the reaction, for. B. by washing out the R.eaktIonsigemisches with water or by treatment with reactive metal oxides, such as. B. calcium oxide, are removed. The exothermicity that frequently occurs is regulated, if appropriate, by cooling or also by careful addition of the catalyst. Ethers of phenols, kres dols, naphthols, oxy-, diphenols, etc. are mentioned as examples of aromatic ethers. Like this: in patent 695z78 for analogous reactions of styrene. indicated, aromatic oxy compounds are capable of a similar reaction, so. -that also in this case the aromatic ethers can partly be replaced by aromatic Oxyver bonds. EXAMPLE 2 parts by weight of tin tetrachloride are added to a mixture of 60 parts by weight of D2-vinylbenzene, 77 parts by weight of p-naphthol ethyl ether and 70 parts by weight of carbon tetrachloride and the mixture is stirred for 12 hours at a temperature not exceeding 20 °. The reaction mixture is diluted with further amounts of carbon tetrachloride and heated to 80 ° for 3 hours with the addition of calcium oxide and fuller's earth. The solvent and a small amount of unreacted (3-vaphthoethyl ether are removed from the filtered solution by distillation. After removal of the volatile constituents, imt by distillation. A vacuum is obtained as much as parts by weight; pale yellow resin that is found in drying oils; -, in aliphatic and aromatic coals = ' hydrogen, as used in paint technology needs to be soluble.

Claims (1)

PATENTANSPRUCH. Abänderung des Verfahrens gemäß Patent 674984, dadurch gekennzeichnet, daß Gemische von Divinylbenzol und aromatischen Äthern mit solchen sauer reagierenden oder säureabspaltenden Substanzen behandelt werden, welche Styrol zu polymerisieren vermögen. PATENT CLAIM. Modification of the process according to patent 674984, characterized in that mixtures of divinylbenzene and aromatic ethers are treated with acidic or acidic substances which are capable of polymerizing styrene.
DE1935I0052775 1935-07-11 1935-07-11 Process for the preparation of reaction products of divinylbenzene Expired DE696287C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE1935I0052775 DE696287C (en) 1935-07-11 1935-07-11 Process for the preparation of reaction products of divinylbenzene

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1935I0052775 DE696287C (en) 1935-07-11 1935-07-11 Process for the preparation of reaction products of divinylbenzene
DE8004891 1937-07-17

Publications (1)

Publication Number Publication Date
DE696287C true DE696287C (en) 1940-09-17

Family

ID=25945018

Family Applications (1)

Application Number Title Priority Date Filing Date
DE1935I0052775 Expired DE696287C (en) 1935-07-11 1935-07-11 Process for the preparation of reaction products of divinylbenzene

Country Status (1)

Country Link
DE (1) DE696287C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE864454C (en) * 1948-05-22 1953-01-26 Houilleres Bassin Du Nord Process for the production of synthetic resins

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE864454C (en) * 1948-05-22 1953-01-26 Houilleres Bassin Du Nord Process for the production of synthetic resins

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