DE1016936B - Process for the production of water-soluble salts from the copolymer of vinylbenzene and maleic anhydride - Google Patents

Process for the production of water-soluble salts from the copolymer of vinylbenzene and maleic anhydride

Info

Publication number
DE1016936B
DE1016936B DED23396A DED0023396A DE1016936B DE 1016936 B DE1016936 B DE 1016936B DE D23396 A DED23396 A DE D23396A DE D0023396 A DED0023396 A DE D0023396A DE 1016936 B DE1016936 B DE 1016936B
Authority
DE
Germany
Prior art keywords
copolymer
water
suspension
vinylbenzene
maleic anhydride
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
DED23396A
Other languages
German (de)
Inventor
Dr Walter Hoenig
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.)
Dynamit Nobel AG
Original Assignee
Dynamit Nobel 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 Dynamit Nobel AG filed Critical Dynamit Nobel AG
Priority to DED23396A priority Critical patent/DE1016936B/en
Publication of DE1016936B publication Critical patent/DE1016936B/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
    • C08F222/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/04—Anhydrides, e.g. cyclic anhydrides
    • C08F222/06—Maleic anhydride
    • C08F222/08—Maleic anhydride with vinyl aromatic monomers
    • 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
    • C08F22/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • C08F22/04—Anhydrides, e.g. cyclic anhydrides

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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 Herstellung von wasserlöslichen Salzen aus dem Mischpolymerisat von Vinylbenzol und Maleinsäureanhydrid Es ist bekannt, die Polymerisation von. Vinylbenzol und Maleinsäureanhydrid in inerten Lösungsmitteln bei einer dem gewünschten Polymerisationsgrad analogen Temperatur so durchzuführen, daß eine Abtrennung des erhaltenen Mischpolymerisates aus der Lösung, z. B. durch Hinzufügen von Wasser oder durch Abdampfen des Lösungsmittels, erfolgen kann. Die: so erhaltenen Produkte zeigen nach dem Eliminieren des Lösungsmittels den Nachteil, daß sie sich auf direktem Wege schwer zu wasserlöslichen Salzen umsetzen lassen, wogegen die Herstellung von z. B. 10- bis 30o/oigen wäßrigen Alkalilösungen leicht gelingt. Es ist auch bekannt, feste Salze, z. B. Ammoniumsalze des Mischpolymerisats, auf die Art herzustellen, daß man das Mischpolymerisat in entsprechend zerkleinerter Form auf trockenem Wege mit Ammoniumkarbonat bzw. Aminoniumdikarbonat umsetzt. Diese Umsetzung geht aber sehr langsam vonstatten und bedarf eines entsprechenden technischen Aufwandes.Process for the production of water-soluble salts from the copolymer of vinylbenzene and maleic anhydride It is known the polymerization of. Vinylbenzene and maleic anhydride in inert solvents at one of the desired Carry out degree of polymerization analogous temperature so that a separation of the copolymer obtained from the solution, for. B. by adding water or by evaporating the solvent. The: products thus obtained show the disadvantage after eliminating the solvent that they affect direct Ways difficult to convert to water-soluble salts, whereas the production of z. B. 10 to 30% aqueous alkali solutions easily succeed. It is also known solid salts, e.g. B. ammonium salts of the copolymer, to produce in the manner that one the copolymer in appropriately comminuted form by dry means with ammonium carbonate or aminonium bicarbonate. But this implementation works proceed very slowly and requires a corresponding technical effort.

Ferner ist es auch bekannt, zu trockenen Salzen, z. B. Alkalisalzen, zu gelangen, indem man aus wäßrigen Alkalisalzlösungen mit Hilfe von Schleppmitteln das Wass:cr entfernt.Furthermore, it is also known to dry salts, e.g. B. alkali salts, to arrive by taking from aqueous alkali salt solutions with the help of entrainers the water: cr removed.

Es wurde nun überraschenderweise gefunden, daß man auf sehr einfache Art und auf direktem Wege zu pulverförmigen wasserlöslichen Salzen des Mischpolymerisates aus Vinylbenzol und Maleinsäureanhydrid gelangt, wenn man die Polymerisa.tion der Monomeren in Form der Suspensionspolymerisation durchführt und die erhaltenen Polymerisationsprodukte in Suspension in Abwesenheit von Wasser mit Hydroxyden der Alkalimetalle bzw. mit trockenem Ammoniak umsetzt. Hierbei führt man die Suspensionspolymerisation so durch, daß man in solchen Lösungsmitteln arbeitet, die Lösungsmittel für die Monomeren sind und denen 5 bis 2011/o eines aliphatisc.hen Ketons, vorzugsweise 101/o z. B. Butanon, zugesetzt sind.It has now surprisingly been found that very simple Type and directly to powdery water-soluble salts of the copolymer from vinylbenzene and maleic anhydride, if the Polymerisa.tion of the Carries out monomers in the form of suspension polymerization and the polymerization products obtained in suspension in the absence of water with hydroxides of the alkali metals or with converts dry ammonia. The suspension polymerization is carried out in such a way that that one works in such solvents, the solvents for the monomers and to which 5 to 2011 / o of an aliphatic ketone, preferably 101 / o z. B. Butanone, are added.

Im Falle der Gewinnung des Natrium- oder Ka.liumsalzes des Mischpolymerisats stellt man. eine, Lösung von Natriumhydroxyd bzw. Kaliumhydroxyd in Butanol her. Diese Lösung, die so viel Alkali enthält, wie zur Bildung dieses Salzes des Mischpolymerisats notwendig ist, wird zu der Suspension. des Mischpolymerisa.ts hinzugefügt, wobei sich das gebildete Alkalisalz abscheidet. Leitet man in die nach der Polymerisation. resultierende Suspension des Mischpolymerisats Ammoniak bis zur Sättigung ein, so bildet sich in glatter Weise ein wasserlösliches Produkt, das ausfällt und abgetrennt werden kann..In the case of obtaining the sodium or potassium salt of the copolymer one puts. a solution of sodium hydroxide or potassium hydroxide in butanol. This solution, which contains as much alkali as needed to form this salt of the copolymer is necessary is added to the suspension. des Mischpolymerisa.ts added, whereby the alkali salt formed separates out. One leads in after the polymerization. resulting suspension of the copolymer ammonia to saturation, see above a water-soluble product is formed smoothly, which precipitates and separates can be..

Das erfindungsgemäße Verfahren, gestattet die direkte Herstellung fester wasserlöslicher Salze des Mischpolymerisats Vinylbenzol-Maleinsäureanhydrid ohne zeitraubende Manipulationen und ohne großen technischen Aufwand.The process according to the invention allows direct production solid water-soluble salts of the copolymer vinylbenzene-maleic anhydride without time-consuming manipulations and without great technical effort.

Beispiel 1 In die aus 52 kg Styrol und 49 kg Maleinsäureanhydrid nach der Polymerisation im Gemisch von 540 1 Toluol mit 60 1 Butanon, nach portionsweisem Eintragen einer Lösung von 1 kg Dilauroylperoxyd in 12,51 Toluol, resultierenden 615 kg Mischpolymerisatsuspension werden bei 25 his 30° C 12,75 kg Ammoniak eingeleitet.Example 1 In the from 52 kg of styrene and 49 kg of maleic anhydride according to the polymerization in a mixture of 540 1 toluene with 60 1 butanone, after portionwise Entering a solution of 1 kg of dilauroyl peroxide in 12.51 of toluene, resulting 615 kg of mixed polymer suspension are passed in at 25 ° to 30 ° C., 12.75 kg of ammonia.

Es entstehen 110 kg eines pulverförmigen wasserlöslichen Produktes.110 kg of a powdery water-soluble product are produced.

Beispiel 2 Zu 300 kg Mischpolymerisatsuspension, wie sie nach Beispiel 1 erhalten werden, wird eine Lösung von 9,8 kg Natriumhydroxyd in 195 1 Butanol hinzugefügt. Es bildet sich bei etwa 30° C nach 4 bis 5 Stunden das Natriumsalz als pulverförmiges wasserlösliches Pulver.Example 2 For 300 kg of copolymer suspension as described in the example 1 is obtained, a solution of 9.8 kg of sodium hydroxide in 195 l of butanol added. The sodium salt is formed after 4 to 5 hours at about 30 ° C as a powdery water-soluble powder.

Claims (3)

PATENTANSPRÜCHE: 1. Verfahren zur Herstellung von wa.sserlösliehen Salzen aus dem Mischpolymerisat von Vinylbenzol und Maleinsäureanhydrid, dadurch gekennzeichnet, daß man die Polymerisation des Mischpolymerisats in Form der Suspensionspolymerisation durchführt und die so erhaltenen Polymerisationsprodukte in Suspension in Abwesenheit von Wasser mit Ammoniak bzw. mit Hydroxyden der Alkalimetalle umsetzt. PATENT CLAIMS: 1. Process for the production of water proceeds Salts from the copolymer of vinylbenzene and maleic anhydride, thereby characterized in that the polymerization of the copolymer is in the form of suspension polymerization carries out and the polymerization products thus obtained in suspension Reacts in the absence of water with ammonia or with hydroxides of the alkali metals. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man in die Suspension des Mischpolymerisats eine Lösung von Alkalihydroxyden in Butanol einträgt. 2. The method according to claim 1, characterized in that one is in the suspension of the copolymer introduces a solution of alkali metal hydroxides in butanol. 3. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man in, die Suspension des Mischpolymerisats Ammoniak bis zur Sättigung einleitet und das so erhaltene wasserlösliche Produkt abtrennt. In Betracht gezogene Druckschriften: Deutsche Patentschrift Nr. 953 562; USA.-Patentschriften Nr. 2 621169, 2 647 886, 2 607 762, 2 490 489, 2 286 062.3. The method according to claim 1, characterized in that ammonia is passed into the suspension of the copolymer until saturation and the water-soluble product thus obtained is separated off. Documents considered: German Patent No. 953 562; U.S. Patent Nos. 2,621,169, 2,647,886, 2,607,762, 2,490,489, 2,286,062 .
DED23396A 1956-07-20 1956-07-20 Process for the production of water-soluble salts from the copolymer of vinylbenzene and maleic anhydride Pending DE1016936B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DED23396A DE1016936B (en) 1956-07-20 1956-07-20 Process for the production of water-soluble salts from the copolymer of vinylbenzene and maleic anhydride

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DED23396A DE1016936B (en) 1956-07-20 1956-07-20 Process for the production of water-soluble salts from the copolymer of vinylbenzene and maleic anhydride

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3030342A (en) * 1960-01-15 1962-04-17 Koppers Co Inc Salts of styrene-maleic anhydride copolymers

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2286062A (en) * 1940-06-01 1942-06-09 Du Pont Process for copolymerizing malkic anhydride and polymerizable vinyl compounds
US2490489A (en) * 1944-02-03 1949-12-06 Du Pont Process for copolymerizing maleic anhydride and styrene
US2607762A (en) * 1948-12-07 1952-08-19 Monsanto Chemicals Dry process manufacture of watersoluble derivatives of styrenemaleic anhydride type heteropolymers
US2621169A (en) * 1948-12-18 1952-12-09 Publicker Ind Inc Process for preparing ammonium salts of copolymer compositions
US2647886A (en) * 1951-05-15 1953-08-04 Monsanto Chemicals Water-soluble heteropolymers from styrene, maleic anhydride and a cross-linking reactant
DE953562C (en) * 1955-02-23 1956-12-06 Basf Ag Process for the production of water-soluble alkali salts from copolymers of vinylbenzenes and maleic anhydride

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2286062A (en) * 1940-06-01 1942-06-09 Du Pont Process for copolymerizing malkic anhydride and polymerizable vinyl compounds
US2490489A (en) * 1944-02-03 1949-12-06 Du Pont Process for copolymerizing maleic anhydride and styrene
US2607762A (en) * 1948-12-07 1952-08-19 Monsanto Chemicals Dry process manufacture of watersoluble derivatives of styrenemaleic anhydride type heteropolymers
US2621169A (en) * 1948-12-18 1952-12-09 Publicker Ind Inc Process for preparing ammonium salts of copolymer compositions
US2647886A (en) * 1951-05-15 1953-08-04 Monsanto Chemicals Water-soluble heteropolymers from styrene, maleic anhydride and a cross-linking reactant
DE953562C (en) * 1955-02-23 1956-12-06 Basf Ag Process for the production of water-soluble alkali salts from copolymers of vinylbenzenes and maleic anhydride

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3030342A (en) * 1960-01-15 1962-04-17 Koppers Co Inc Salts of styrene-maleic anhydride copolymers

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