DE965444C - Process for the polymerization of vinyl compounds - Google Patents

Process for the polymerization of vinyl compounds

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Publication number
DE965444C
DE965444C DEC10561A DEC0010561A DE965444C DE 965444 C DE965444 C DE 965444C DE C10561 A DEC10561 A DE C10561A DE C0010561 A DEC0010561 A DE C0010561A DE 965444 C DE965444 C DE 965444C
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Germany
Prior art keywords
polymerization
vinyl compounds
vinyl
compounds
soluble
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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
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DEC10561A
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German (de)
Inventor
Dr Heinrich Wenning
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.)
Huels AG
Original Assignee
Chemische Werke Huels AG
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Publication date
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Priority to DEC10561A priority Critical patent/DE965444C/en
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Publication of DE965444C publication Critical patent/DE965444C/en
Expired legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/12Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes

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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)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Description

Verfahren zur Polymerisation von Vinylverbindungen Es ist bekannt, Vinylverbindungen, wie Styrol, Vinylester, Acrylsäureester oder deren Gemische, in wäßrigem Medium in Gegenwart fester, pulverförmiger Stoffe, die in der zu polymerisierenden Vinylverbindung unlöslich sind, z. B. Bariumsulfat, Erdalkaliphosphate, Aluminiumoxyd, unter mechanischer Bewegung zu polymerisieren, wobei die Polymerisate in Form von mehr oder minder feinen Körnern oder Perlen erhalten werden. Ein ähnliches Ergebnis liefert auch die Polymerisation von Vinylverbindungen in Gegenwart hochmolekularer organischer, in Wasser kolloidal löslicher Verbindungen, wie Gelatine, Celluloseäther, Polyvinylalkohol, Polyacrylsäure, Polyv:nylpyrrolidon usw. Man bezeichnet diese Art der Polymerisation als Suspensionspolymerisation, sie wird unter -Verwendung von in den Monomeren löslichen oder unlöslichen Katalysatoren ausgeführt.Process for the polymerization of vinyl compounds It is known Vinyl compounds such as styrene, vinyl esters, acrylic acid esters or their mixtures, in an aqueous medium in the presence of solid, powdery substances in the to be polymerized Vinyl compound are insoluble, e.g. B. barium sulfate, alkaline earth phosphates, aluminum oxide, to polymerize with mechanical movement, the polymers in the form of more or less fine grains or pearls can be obtained. A similar result also provides the polymerization of vinyl compounds in the presence of high molecular weight organic compounds that are colloidally soluble in water, such as gelatine, cellulose ether, Polyvinyl alcohol, polyacrylic acid, polyvinylpyrrolidone, etc. These are called Type of polymerization as suspension polymerization, it is under use carried out by catalysts soluble or insoluble in the monomers.

Es wurde gefunden, daß man Vinylverbindungen besonders vorteilhaft mit Hilfe von in den Monomeren löslichen Katalysatoren in wäßriger Suspension unter mechanischer Bewegung polymerisieren kann, wenn man in Gegenwart geringer Mengen von Silikonölen (etwa o,ooi bis o,i Gewichtsprozent bezogen auf die monomeren Vinylverbindungen) arbeitet.It has been found that vinyl compounds are particularly advantageous with the aid of catalysts soluble in the monomers in aqueous suspension mechanical movement can polymerize if one is in the presence of small amounts of silicone oils (about o, ooi to o, i percent by weight based on the monomeric vinyl compounds) is working.

Unter Silikonölen werden Organo-polysiloxane und Organo-oxypolysiloxane verstanden, die einen linearen bzw. wenig verzweigten Molekülaufbau besitzen und etwa der Formel MDXM entsprechen (vgl. R o c h o w , Einführung in die Chemie der S ilikone, S. 86 bis 97). Diese Silikonöle besitzen Viskositäten von 2o bis 2ooo cSt bei 2o°, sie sind im allgemeinen in Wasser nicht oder nur schwer löslich, lösen sich dagegen in den monomeren Vinylverbindungen und verhindern ein Zusammenklumpen der entstehenden Polymerisate im Verlaufe der Polymerisation, so daß das Polymerisat in einer körnigen oder kugeligen Form anfällt.Organo-polysiloxanes and organo-oxypolysiloxanes are classified as silicone oils understood the one linear or slightly branched molecular structure and roughly correspond to the formula MDXM (see R o c h o w, introduction to Die Chemie der Silikone, pp. 86 to 97). These silicone oils have viscosities from 2o to 2ooo cSt at 2o °, they are generally not or only with difficulty in water soluble, but dissolve in the monomeric vinyl compounds and prevent them from dissolving The resulting polymers clump together in the course of the polymerization, see above that the polymer is obtained in a granular or spherical shape.

Für die Durchführung des Verfahrens geeignete Vinylverbindungen sind beispielsweise Vinylidenchlorid, Vinylchlorid Vinylcyani@d, Vinylidencyaniid, Acrylnitril und deren Gemische.Vinyl compounds suitable for carrying out the process are for example vinylidene chloride, vinyl chloride vinylcyani @ d, vinylidenecyaniide, acrylonitrile and their mixtures.

In den monomeren Vinylverbindungen geeignete lösliche Katalysatoren sind beispielsweise Benzoylsuperoxyd und dessen Substitutionsprodukte, Cumolhydroperoxyd, Lauroylperoxyd, Peroxyde von tertiären Alkoholen, wie Ditertiärbutylperoxyd, ferner Azobuttersäuredinitril, dessen Homologe und Substitutionsprodukte und andere Verbindungen, die unter den Reaktionsbedingungen in Radikale zerfallen.Suitable soluble catalysts in the monomeric vinyl compounds are for example benzoyl superoxide and its substitution products, cumene hydroperoxide, Lauroyl peroxide, peroxides of tertiary alcohols, such as di-tertiary butyl peroxide, also Azobutyric acid dinitrile, its homologues and substitution products and other compounds, which decompose into radicals under the reaction conditions.

Auf die Größe der entstehenden Polymerisatkörner haben die angewandte Menge des Silikonöls, das Verhältnis der wäßrigenPhase zur organischen Phase sowie die mechanische Bewegung, z. B. durch Rühren, Schütteln oder Beschallen, während der Polymerisation starken Einfluß. Will man gröbere Körner erzielen, so wird ein weites Phasenverhältnis und eine geringe mechanische Turbulenz gewählt, während man zur Erzielung feinerer Körner ein enges Phasenverhältnis und eine hohe mechanische Turbulenz benötigt.On the size of the resulting polymer grains have the applied Amount of silicone oil, the ratio of the aqueous phase to the organic phase as well as the mechanical movement, e.g. B. by stirring, shaking or sonication while the polymerization has a strong influence. If you want to achieve coarser grains, a wide phase ratio and low mechanical turbulence selected while A close phase ratio and a high mechanical ratio are used to obtain finer grains Turbulence needed.

Zur Durchführung des Verfahrens werden das anzuwendende Silikonöl und der Katalysator der zu polymerisierenden Vinylverbindung zugesetzt und das Ganze in Wasser unter kräftigem Rühren suspendiert. Das Verhältnis von organischer Phase zu wäßriger Phase kann sich in weiten Grenzen bewegen; im allgemeinen verwendet man auf ioo Teile organische Phase 3oo bis 40o Teile wäßrige Phase, doch kann man auch mit anderen Mengenverhältnissen, beispielsweise mit ioo Teilen organischer Phase und ioo Teilen wäßriger Phase wie auch mit ioo Teilen organischer Phase und 8oo Teilen wäßriger Phase arbeiten. Die bei der Polymerisation einzuhaltende Temperatur richtet sich nach der Zerfallsgeschwindigkeit dies angewandten Katalysators und liegt im allgemeinen im Bereich zwischen 3o und 70°, vorzugsweise im Bereich zwischen 45 und 55°, so z.B. wenn Azoisobuttersäuredinitril als Katalysator Verwendung findet.To carry out the procedure, the silicone oil to be used and the catalyst is added to the vinyl compound to be polymerized and the whole suspended in water with vigorous stirring. The ratio of organic phase to aqueous phase can move within wide limits; generally used one to 100 parts of organic phase 3oo to 40o parts of aqueous phase, but you can also with other proportions, for example with 100 parts of organic Phase and 100 parts of aqueous phase as well as 100 parts of organic phase and Work 8oo parts of the aqueous phase. The temperature to be maintained during the polymerization depends on the rate of disintegration of the catalyst used and is generally in the range between 3o and 70 °, preferably in the range between 45 and 55 °, e.g. when azoisobutyric acid dinitrile is used as a catalyst.

Die erhaltenen Polymerisatkörner werden vom Wasser durch Schleudern oder Filtrieren getrennt und ergeben nach dem Trocknen Pulver von sehr niederem Schüttvolumen, d. h. hohem Schüttgewicht. Sie sind für die Weiterverarbeitung in Extrudern besonders geeignet und liefern Formkörper, die eine hervorragende Stabilität und Klarheit besitzen; außerdem sind sie wegen des Fehlens elektrisch leitender Stoffe besonders für den Einsatz auf dem elektrischen Sektor geeignet.The polymer grains obtained are removed from the water by spinning or filtering separately and, after drying, gives powder of very low Bulk volume, d. H. high bulk weight. They are ready for further processing in Extruders are particularly suitable and provide moldings that have excellent stability and have clarity; in addition, due to the lack of them, they are more electrically conductive Substances particularly suitable for use in the electrical sector.

Beispiel io kg eines Gemisches, bestehend aus 8,5 kg Vinylidenchlorid und 1,5 kg Vinylchlorid, werden in Gegenwart von 5 g eines Silikonöles, z. B. Methylpolysiloxan von der Viskosität etwa ioo cSt, und 30 g Azobuttersäurenitril in io 1 Wasser unter kräftigem Rühren dispergiert und 25 Stunden lang auf 45° erhitzt. Nach dieser Zeit sind etwa 65 °/o der Monomeren polymerisiert. Man bricht sodann die Polymerisation durch Entspannen ab und kann das entstandene Polymerisat durch Filtration leicht gewinnen. Man trocknet bei Temperaturen zwischen 50 und ioo° und erhält ein Material, das sich im Extruder unter Zusatz von Weichmachungsmitteln und Stabilisatoren zu sehr hellen Fäden oder Folien verarbeiten läßt.Example 10 kg of a mixture consisting of 8.5 kg of vinylidene chloride and 1.5 kg of vinyl chloride, in the presence of 5 g of a silicone oil, for. B. methylpolysiloxane with a viscosity of about 100 cSt, and 30 g of azobutyronitrile dispersed in 10 1 of water with vigorous stirring and heated to 45 ° for 25 hours. After this time about 65% of the monomers have polymerized. The polymerization is then terminated by letting down the pressure and the resulting polymer can easily be obtained by filtration. It is dried at temperatures between 50 and 100 ° and a material is obtained which can be processed in the extruder with the addition of plasticizers and stabilizers to give very light-colored threads or films.

Claims (1)

PATENTANSPRUCH: Verfahren zur Polyrnerisation von Vinylverbindungen mit Hilfe von in den Monomeren löslichen Katalysatoren in wäßriger Suspension unter mechanischer Bewegung, dadurch gekennzeichnet, daß man in Gegenwart geringer Mengen von S.ilikonölen arbeitet. In Betracht gezogene Druckschriften: Deutsche Patentschriften Nr. 8oi 746, 878 863, 879 315, 9oo 612, 919 432; R o c h o w, Einführung in die Chemie der Silikone, S. 9o. Claim: Process for the polymerization of vinyl compounds with the aid of catalysts soluble in the monomers in aqueous suspension with mechanical agitation, characterized in that small amounts of silicone oils are used. Considered publications: German Patent Specifications No. 8oi 746, 878 863, 879 3 1 5, 9oo 612, 9 1 9 432; R ochow, Introduction to the Chemistry of Silicones, p. 9o.
DEC10561A 1955-01-13 1955-01-13 Process for the polymerization of vinyl compounds Expired DE965444C (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1076373B (en) * 1957-01-09 1960-02-25 Hoechst Ag Process for the production of polyvinyl chloride dispersions
DE3524302A1 (en) * 1985-07-06 1987-01-08 Hoechst Ag Sinterable, finely divided moulding composition based on vinyl chloride polymers

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE801746C (en) * 1947-08-18 1951-01-22 Basf Ag Process for the production of granular polymers of vinyl compounds
DE878863C (en) * 1950-12-16 1953-06-08 Hoechst Ag Process for the production of pearlescent or granular polymerization products
DE879315C (en) * 1939-03-11 1953-06-11 Hoechst Ag Process for the production of fine-grained or pearl-shaped polymers
DE900612C (en) * 1934-09-17 1953-12-28 Ici Ltd Process for the production of granular or spherical polymerisation products
DE919432C (en) * 1950-05-17 1954-10-21 Styrene Products Ltd Process for the suspension polymerization of unsaturated organic compounds with a CH: C <group in the molecule

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE900612C (en) * 1934-09-17 1953-12-28 Ici Ltd Process for the production of granular or spherical polymerisation products
DE879315C (en) * 1939-03-11 1953-06-11 Hoechst Ag Process for the production of fine-grained or pearl-shaped polymers
DE801746C (en) * 1947-08-18 1951-01-22 Basf Ag Process for the production of granular polymers of vinyl compounds
DE919432C (en) * 1950-05-17 1954-10-21 Styrene Products Ltd Process for the suspension polymerization of unsaturated organic compounds with a CH: C <group in the molecule
DE878863C (en) * 1950-12-16 1953-06-08 Hoechst Ag Process for the production of pearlescent or granular polymerization products

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1076373B (en) * 1957-01-09 1960-02-25 Hoechst Ag Process for the production of polyvinyl chloride dispersions
DE3524302A1 (en) * 1985-07-06 1987-01-08 Hoechst Ag Sinterable, finely divided moulding composition based on vinyl chloride polymers

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