DE1129699B - Process for the production of binary and internal copolymers of styrene - Google Patents

Process for the production of binary and internal copolymers of styrene

Info

Publication number
DE1129699B
DE1129699B DEL37355A DEL0037355A DE1129699B DE 1129699 B DE1129699 B DE 1129699B DE L37355 A DEL37355 A DE L37355A DE L0037355 A DEL0037355 A DE L0037355A DE 1129699 B DE1129699 B DE 1129699B
Authority
DE
Germany
Prior art keywords
styrene
parts
binary
copolymers
weight
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.)
Pending
Application number
DEL37355A
Other languages
German (de)
Inventor
Emanuele Condorelle
Levio Spano
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.)
L I R C LAB ITALIANI DI RICERC
Original Assignee
L I R C LAB ITALIANI DI RICERC
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 L I R C LAB ITALIANI DI RICERC filed Critical L I R C LAB ITALIANI DI RICERC
Publication of DE1129699B publication Critical patent/DE1129699B/en
Pending legal-status Critical Current

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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
    • 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
    • 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
    • C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/42—Nitriles
    • C08F220/44—Acrylonitrile

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

Description

DEUTSCHESGERMAN

PATENTAMTPATENT OFFICE

L37355IVd/39cL37355IVd / 39c

ANMELDETAG: 26. OKTOB ER 1960REGISTRATION DATE: OCTOBER 26, 1960

BEKANNTMACHUNG DER ANMELDUNG UNDAUSGABEDER AUSLEGESCHRIFT: 17. MAI 1962NOTICE THE REGISTRATION ANDOUTPUTE EDITORIAL: MAY 17, 1962

Dei Erfindung bezieht sich auf ein Verfahren zur Herstellung von binären und ternären Mischpolymerisaten des Styrols. Sie wird im einzelnen dadurch gekennzeichnet, daß man ein Gemisch von Styrol und Mesacon- bzw. Citraconsäuredimethylester und gegebenenfalls Acrylnitril in Gegenwart von Peroxyden, vornehmlich organischen Peroxyden oder Hydroperoxyden, als Katalysator, besonders bei 50 bis 1500C, einer (Block-)Polymerisation unterwirft. Als Katalysatoren seien beispielsweise Benzoyl- und Laurylperoxyd genannt. Die hiervon erforderlichen Mengen betragen im allgemeinen nicht mehr als etwa2°/o.The invention relates to a process for the production of binary and ternary copolymers of styrene. It is specifically characterized in that a mixture of styrene and mesaconic or citraconate and optionally acrylonitrile in the presence of peroxides, especially organic peroxides or hydroperoxides, as a catalyst, especially at 50 to 150 0 C, a (block) polymerization subject. Examples of catalysts that may be mentioned are benzoyl and lauryl peroxide. The amounts required thereof are generally not more than about 2%.

Bei den Mischpolymerisaten nach der Erfindung schwankt das Mengenverhältnis von Styrol und Mesacon- bzw. Citracondimethylester zwischen 30 bis 90 Teilen Styrol und 70 bis 10 Teilen Diester. Bei den ternären Mischpolymerisaten beträgt die Menge des Acrylnitrils maximal 30 Gewichtsprozent der gesamten Monomeren. Die Polymerisierung kann einen bis mehrere Tage in Anspruch nehmen. Im allgemeinen kann man sie ziemlich lang ausdehnen, ohne daß besondere Nachteile festgestellt werden können.In the copolymers according to the invention, the ratio of styrene and varies Mesacon or citracon dimethyl esters between 30 to 90 parts of styrene and 70 to 10 parts of diester. In the case of the ternary copolymers, the amount of acrylonitrile is a maximum of 30 percent by weight of the total monomers. The polymerization can take one to several days. In general you can extend it quite long without noticing particular disadvantages can.

In Abwesenheit von Katalysatoren geht die Polymerisierung langsamer vonstatten, und die so entstehenden Polymeren weisen eine relativ hohe Viskosität auf.In the absence of catalysts, the polymerization proceeds more slowly, and so does the resulting Polymers have a relatively high viscosity.

Die gebildeten Mischpolymerisate sind lichtdurchlässig, zeigen gute mechanische Eigenschaften und sind unlöslich. Vor allem im Falle der ternären Polymeren liegt sogar Beständigkeit gegenüber Lösungsmitteln vom Typ Benzol vor.The copolymers formed are translucent, show good mechanical properties and are insoluble. In the case of ternary polymers in particular, there is even resistance to solvents of the benzene type.

Die Mischpolymerisate können mit den normalen Verfahren des Strangpressens und des Spritzgusses weiter verarbeitet werden, genau wie es bei den thermoplastischen Kunstharzen der Fall ist.The copolymers can be processed using the normal extrusion and injection molding processes further processed, just as it is the case with thermoplastic synthetic resins.

Die Erfindung wird an Hand einiger Ausführungsbeispiele näher erläutert. Die Prozentzahlen beziehen sich auf Gewichtsteile.The invention is explained in more detail using a few exemplary embodiments. Relate the percentages based on parts by weight.

Beispiel 1example 1

300 Teile Dimethylcitraconat werden mit 700 Teilen handelsüblichen Styrols gemischt und diesem 0,7 Teile Benzylperoxyd zugesetzt. Das Gemisch wird dann in einem thermoregulierten Wasserbad 4 Tage auf 70° C gehalten. Nach Ablauf dieser Zeit ist die Mischpolymerisation abgeschlossen.300 parts of dimethyl citraconate are mixed with 700 parts of commercial styrene and this 0.7 parts of benzyl peroxide were added. The mixture is then placed in a thermoregulated water bath for 4 days kept at 70 ° C. After this time has elapsed, the copolymerization is complete.

Beispiel 2Example 2

Man verfährt wie bei Beispiel 1, verwendet aber 400 Teile Dimethylcitraconat und 600 Teile handels-Verfahren zur HerstellungThe procedure is as in Example 1, except that 400 parts of dimethyl citraconate and 600 parts of commercial process are used for the production

von binären und ternärenof binary and ternary

Mischpolymerisaten des StyrolsCopolymers of styrene

Anmelder:Applicant:

L. I. R. C. Laboratori Italiani
ίο di Ricerca Chimica S.p.A.,LIRC Laboratori Italiani
ίο di Ricerca Chimica SpA,

Mailand (Italien)Milan (Italy)

Vertreter:Representative:

Dipl.-Ing. Dipl.-Chem. Dr. phil. Dr. techn. J. Reitstötter und Dr.-Ing. W. Bunte, Patentanwälte,Dipl.-Ing. Dipl.-Chem. Dr. phil. Dr. techn. J. Reitstötter and Dr.-Ing. W. Bunte, patent attorneys,

München 15, Haydnstr. 5Munich 15, Haydnstr. 5

Beanspruchte Priorität:
Italien vom 13. November 1959 (Nr. 18 857)Claimed priority:
Italy of November 13, 1959 (No. 18 857)

Levio Spano, Cesano Maderno,Levio Spano, Cesano Maderno,

und Emanuele Condorelle, Mailand (Italien),and Emanuele Condorelle, Milan (Italy),

sind als Erfinder genannt wordenhave been named as inventors

üblichen Styrols. Als Katalysator werden 10 Teile Laurylperoxyd verwendet.usual styrene. 10 parts of lauryl peroxide are used as the catalyst.

Beispiel 3Example 3

Es wird wie in Beispiel 1 oder 2 vorgegangen, nur mit dem Unterschied, daß man an Stelle des Dimethylcitraconats die äquivalente Menge Dimethylmesaconat zur Reaktion bringt. Die Polymerisierung erfolgt in derselben Weise.The procedure is as in Example 1 or 2, the only difference being that instead of the dimethyl citraconate the equivalent amount of dimethyl mesaconate reacts. The polymerization takes place in same way.

Beispiel 4Example 4

Man geht von einem Monomerengemisch aus, das aus 620 Teilen Styrol, 320 Teilen Dimethylcitraconat oder -mesaconat und 60 Teilen Acrylnitril zusammengesetzt ist. Als Reaktionsbeschleuniger verwendet man 5 Teile Laurylperoxyd. Die Mischung wird 36 Stunden bei 500C, 36 Stunden bei 8O0C und 10 Stunden bei 12O0C erhitzt.The starting point is a monomer mixture composed of 620 parts of styrene, 320 parts of dimethyl citraconate or mesaconate and 60 parts of acrylonitrile. 5 parts of lauryl peroxide are used as the reaction accelerator. The mixture is heated for 36 hours at 50 0 C, 36 hours at 8O 0 C and 10 hours at 12O 0 C.

Claims (4)

PATENTANSPRÜCHE:PATENT CLAIMS: 1. Verfahren zur Herstellung von binären und ternären Mischpolymerisaten des Styrols, dadurch 1. Process for the preparation of binary and ternary copolymers of styrene, thereby 209 580/473209 580/473 gekennzeichnet, daß man ein Gemisch von Styro} und Mesacon- bzw. Citraconsäuredimethylester, und gegebenenfalls Acrylnitril, in Gegenwart von Peroxyden, vornehmlich organischen Peroxyden oder Hydroperoxyden, als Katalysator, besonders bei 50 bis 1500C, einer (Block-)Polymerisation unterwirft. characterized in that a mixture of Styro} and mesaconic or citraconic acid dimethyl ester, and optionally acrylonitrile, in the presence of peroxides, mainly organic peroxides or hydroperoxides, as a catalyst, especially at 50 to 150 0 C, is subjected to a (block) polymerization. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß das Mengenverhältnis von Styrol zu den Diestern 30 bis 90 Gewichtsteile zu xo 70 bis 10 Gewichtsteile beträgt.2. The method according to claim 1, characterized in that the quantitative ratio of Styrene to the diesters is 30 to 90 parts by weight to xo 70 to 10 parts by weight. 3. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß der Anteil an Acrylnitril maximal 30 Gewichtsprozent beträgt.3. The method according to claim 1, characterized in that that the proportion of acrylonitrile is a maximum of 30 percent by weight. 4. Verfahren nach den Ansprüchen 1 bis 3, dadurch gekennzeichnet, daß als Katalysator Benzoylperoxyd oder Laurylperoxyd verwendet werden.4. Process according to Claims 1 to 3, characterized in that the catalyst used is benzoyl peroxide or lauryl peroxide can be used. In Betracht gezogene Druckschriften:
Krczil, Kurzes Handbuch der Polymerisationstechnik, Bd. II (1941), Mehrstoffpolymerisation, S. 283.Considered publications:
Krczil, Kurzes Handbuch der Polymerisierungstechnik, Vol. II (1941), Mehrstoffpolymerisierung, p. 283. Bei der Bekanntmachung der Anmeldung ist eine Tabelle ausgelegt worden.A table was laid out when the application was announced. © 209580/473 5.62© 209580/473 5.62
DEL37355A 1959-11-13 1960-10-26 Process for the production of binary and internal copolymers of styrene Pending DE1129699B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT886890X 1959-11-13

Publications (1)

Publication Number Publication Date
DE1129699B true DE1129699B (en) 1962-05-17

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Application Number Title Priority Date Filing Date
DEL37355A Pending DE1129699B (en) 1959-11-13 1960-10-26 Process for the production of binary and internal copolymers of styrene

Country Status (2)

Country Link
DE (1) DE1129699B (en)
GB (1) GB886890A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3101887A1 (en) * 1981-01-22 1982-09-02 Hoechst Ag, 6000 Frankfurt "METHOD FOR PRODUCING COPOLYMERISATS AND USE OF THE PRODUCTS RECEIVED"

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3101887A1 (en) * 1981-01-22 1982-09-02 Hoechst Ag, 6000 Frankfurt "METHOD FOR PRODUCING COPOLYMERISATS AND USE OF THE PRODUCTS RECEIVED"

Also Published As

Publication number Publication date
GB886890A (en) 1962-01-10

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