DE631756C - Process for dissolving polymeric acrylic acid nitrile - Google Patents

Process for dissolving polymeric acrylic acid nitrile

Info

Publication number
DE631756C
DE631756C DEI50421D DEI0050421D DE631756C DE 631756 C DE631756 C DE 631756C DE I50421 D DEI50421 D DE I50421D DE I0050421 D DEI0050421 D DE I0050421D DE 631756 C DE631756 C DE 631756C
Authority
DE
Germany
Prior art keywords
solution
acrylic acid
acid nitrile
polymeric acrylic
pyridine
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
DEI50421D
Other languages
German (de)
Inventor
Dr Herbert Rein
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 DEI50421D priority Critical patent/DE631756C/en
Application granted granted Critical
Publication of DE631756C publication Critical patent/DE631756C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
    • C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
    • C08J3/096—Nitrogen containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/18—Homopolymers or copolymers of nitriles
    • C08L33/20—Homopolymers or copolymers of acrylonitrile
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/02—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D01F6/18—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds from polymers of unsaturated nitriles, e.g. polyacrylonitrile, polyvinylidene cyanide
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
    • C08J2333/18—Homopolymers or copolymers of nitriles
    • C08J2333/20—Homopolymers or copolymers of acrylonitrile
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L89/00—Compositions of proteins; Compositions of derivatives thereof

Description

Verfahren zur Lösung von polymerem Acrylsäurenitril Der Verarbeitung von polymerem Acrylsäurenitril standen bisher Schwierigkeiten im Wege, weil dieser Körper mit keinem der bekannten Mittel in Lösung zu bringen war. Es wurde nun gefunden, daß die-Lösung des polymeren Acrylsäurenitrils bei der Umsetzung von Pyridin oder seinen Homologen mit substituierten Alkylhalogeniden in den entstehenden, in der Wärme verflüssigten quartären Pyridiniumbasen erfolgt. Diese Lösungen eignen sich zur Herstellung von Formkörpern, Filmen oder Fäden. Es ist hierbei nicht erforderlich, daß Halogenverbindung und Pyridin in molekularem Verhältnis angewendet werden, sondern es kann auch ein überschuß an Pyridin Verwendung finden. Ebenso können den Lösungen unter Umständen geeignete Lösungs- oder Verdünnungsmittel zugesetzt werden. Die Ausfällung des Polyacrylsäurenitrils aus diesen Lösungen kann nach den an sich bekannten Verfahren durch Wasser, Säuren, Lösungsmittel usw. erfolgen.Method for dissolving polymeric acrylonitrile processing of polymeric acrylonitrile have hitherto stood in the way of difficulties because of this Body could not be brought into solution with any of the known means. It has now been found that the solution of the polymeric acrylonitrile in the reaction of pyridine or its homologues with substituted alkyl halides in the resulting, in the Heat liquefied quaternary pyridinium bases takes place. These solutions are suitable for the production of moldings, films or threads. It is not necessary to that halogen compound and pyridine are used in a molecular ratio, but an excess of pyridine can also be used. Likewise, the solutions suitable solvents or diluents may be added. the Precipitation of the polyacrylonitrile from these solutions can be carried out according to the methods known per se Process by water, acids, solvents, etc. take place.

Beispiel i Sog fein gepulvertes Polyacrylsäurenitril werden in eine Mischung von io5o g Benzylchlorid und 8oo g Pyridin eingetragen und unter Rühren auf etwa 115° erhitzt. Bei der Umsetzung zwischen Benzylchlorid und Pyridin zu Benzyl-Pyridiniumchlorid geht das Poiyacrylsäurenitril spontan in Lösung. Es entsteht eine rotbraune, in der Wärme viscose Lösung, die beim Erkalten koaguliert. Beispiel a iaoo g Pyridin und 700 9 Benzylchlorid werden erwärmt und unter Rühren j e 3 o g Casein, zerkleinerte Hydratcellulose und Polyacrylsäurenitril eingetragen. Die Temperatur wird auf 95 bis 115° gehalten. Nach kurzer Zeit gehen alle festen Bestandteile unter starker Quellung in Lösung, und es resultiert eine gelbbraune, etwas trübe viscose Lösung.Example i Finely powdered polyacrylonitrile is introduced into a mixture of 1050 g of benzyl chloride and 800 g of pyridine and heated to about 115 ° with stirring. In the reaction between benzyl chloride and pyridine to form benzyl-pyridinium chloride, the polyacrylic acid nitrile goes into solution spontaneously. The result is a red-brown solution that is viscous when heated and coagulates when it cools. Example aoo g of pyridine and 700 g of benzyl chloride are heated and, with stirring, 3 og each of casein, crushed hydrate cellulose and polyacrylic acid nitrile are added. The temperature is kept at 95 to 115 °. After a short time, all the solid constituents go into solution with severe swelling, and a yellow-brown, somewhat cloudy, viscous solution results.

Beispiel 3 3- zerkleinerte Hydratcellulose, 3 g Casein und 3 g Polyacrylsäurenitril werden unter Rühren in einer Mischung von ioo g Pyridin und 8o g Chloressigsäureäthylester erwärmt, bis die exotherme Umsetzung- zwischen Halogenverbindung und Amin einsetzt. Man hält von da ab die Temperatur auf ioo bis 115°, wobei allmählich eine hochviscose braunrote Lösung erhalten wird. Beispiel q. 5 Teile fein gepulvertes Polyacrylsäurenitril werden wie in Beispiel i in eine Mischung von 95 Teilen Picolinbasen (technisch ) und 125 Teilen Benzylchlorid eingetragen und unter Erwärmeü gerührt, bis Lösung eingetreten ist. Man erhält eine braune, in .der- Wärme -hochviscose Lösung.Example 3 3- comminuted hydrate cellulose, 3 g of casein and 3 g of polyacrylonitrile are heated with stirring in a mixture of 100 g of pyridine and 80 g of ethyl chloroacetate until the exothermic reaction between the halogen compound and the amine begins. From then on, the temperature is kept at 100 to 115 °, a highly viscous brown-red solution being gradually obtained. Example q. 5 parts of finely powdered polyacrylonitrile are introduced into a mixture of 95 parts of picolin bases (technical) and 125 parts of benzyl chloride, as in Example i, and the mixture is stirred with heating until it has dissolved. A brown solution of high viscosity in the heat is obtained.

Claims (3)

PATENTANSPRÜCHE: , ,@. i. Verfahren zur. Lösung von polymerem Acrylsäurenitrxl, dadurch gekennzeichnet, daß diese Löseng,'bei 'der Umsetzung von Pyridin ode'Y @ seinen Homologen mit substituierten Alkylhalogeniden in den entstehenden, in der Wärme ver-.fiüssigten quartären Pyridiniumbasen erfolgt. PATENT CLAIMS:,, @. i. Procedure for. Solution of polymeric acrylic acid nitride, characterized in that this dissolution takes place 'during' the reaction of pyridine or its homologues with substituted alkyl halides in the heat-liquefied quaternary pyridinium bases formed. 2. Verfahren nach Anspruch r, dadurch gekennzeichnet, daß die Lösung gleichzeitig in Gegenwart von freier Pyridinbase erfolgt. 2. Procedure according to Claim r, characterized in that the solution is simultaneously in the presence of free pyridine base takes place. 3. Verfahren nach Anspruch i und 2, dadurch gekennzeichnet, daß die Lösung in Gegenwart von Polypeptiden oder Cellulose erfolgt.3. The method according to claim i and 2, characterized in that that the solution takes place in the presence of polypeptides or cellulose.
DEI50421D 1934-08-21 1934-08-22 Process for dissolving polymeric acrylic acid nitrile Expired DE631756C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI50421D DE631756C (en) 1934-08-21 1934-08-22 Process for dissolving polymeric acrylic acid nitrile

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE461675X 1934-08-21
DEI50421D DE631756C (en) 1934-08-21 1934-08-22 Process for dissolving polymeric acrylic acid nitrile

Publications (1)

Publication Number Publication Date
DE631756C true DE631756C (en) 1936-06-26

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
DEI50421D Expired DE631756C (en) 1934-08-21 1934-08-22 Process for dissolving polymeric acrylic acid nitrile

Country Status (1)

Country Link
DE (1) DE631756C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE975539C (en) * 1943-06-23 1961-12-28 Du Pont Process for the production of stable, spinnable, essentially colorless solutions of polyacrylonitrile

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE975539C (en) * 1943-06-23 1961-12-28 Du Pont Process for the production of stable, spinnable, essentially colorless solutions of polyacrylonitrile

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