DE1520703B2 - PROCESS FOR THE MANUFACTURING OF THERMOPLASTIC HOMOPOLYMERIZED OR COPOLYMERIZED PRODUCTS USING FUMAR ACID ESTERS - Google Patents

PROCESS FOR THE MANUFACTURING OF THERMOPLASTIC HOMOPOLYMERIZED OR COPOLYMERIZED PRODUCTS USING FUMAR ACID ESTERS

Info

Publication number
DE1520703B2
DE1520703B2 DE1964R0038235 DER0038235A DE1520703B2 DE 1520703 B2 DE1520703 B2 DE 1520703B2 DE 1964R0038235 DE1964R0038235 DE 1964R0038235 DE R0038235 A DER0038235 A DE R0038235A DE 1520703 B2 DE1520703 B2 DE 1520703B2
Authority
DE
Germany
Prior art keywords
acid esters
fumaric acid
thermoplastic
homopolymerized
manufacturing
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.)
Granted
Application number
DE1964R0038235
Other languages
German (de)
Other versions
DE1520703A1 (en
Inventor
Friedrich Dipl.-Chem. Dr.; Tietz Wolfgang Dipl.-Chem. Dr.; 4102 Homberg Engelhardt
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.)
Wintershall Dea Deutschland AG
Original Assignee
Deutsche Texaco 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
Priority claimed from DER34272A external-priority patent/DE1176871B/en
Application filed by Deutsche Texaco AG filed Critical Deutsche Texaco AG
Priority to DE1964R0038235 priority Critical patent/DE1520703B2/en
Publication of DE1520703A1 publication Critical patent/DE1520703A1/en
Publication of DE1520703B2 publication Critical patent/DE1520703B2/en
Granted 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
    • 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
    • C08F22/10—Esters
    • C08F22/12—Esters of phenols or saturated alcohols
    • C08F22/14—Esters having no free carboxylic acid groups

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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)
  • Polyesters Or Polycarbonates (AREA)

Description

Es ist bereits bekannt, Malein- und/oder Fumarsäureester von linearen oder verzweigten primären, sekundären oder tertiären Alkoholen zusammen mit Vinylchloracetat zu polymerisieren. Durch den Einsatz von Vinylchloracetat ist es möglich, erhöhte Ausbeuten zu erhalten.It is already known that maleic and / or fumaric acid esters of linear or branched primary, to polymerize secondary or tertiary alcohols together with vinyl chloroacetate. Because of the engagement from vinyl chloroacetate it is possible to obtain increased yields.

Gegenstand des Hauptpatents 1176 871 ist ein Verfahren zur.Her stellung thermoplastischer Homo- und Copolymerisate nach dem Blockverfahren (Polymerisation in Substanz) in Gegenwarttadikalbildender Katalysatoren unter Verwendung von Fumarsäureestern sekundärer Alkohole.The subject of the main patent 1176 871 is a method zur.Her position thermoplastic homo- and copolymers by the block process (bulk polymerization) in the presence of radical-forming agents Catalysts using fumaric acid esters of secondary alcohols.

Gegenstand der Zusatzpatentanmeldung 1 520 702 zum Patent 1176 871 ist, daß man bei der Herstellung dieser thermoplastischen Homo- oder Copolymerisate an Stelle der Polymerisation in Substanz auch andere an sich bekannte Polymerisationsmethoden, beispielsweise Lösungs-, Suspensions- oder Emulsionspolymerisation, anwenden kann.The subject of the additional patent application 1 520 702 to the patent 1176 871 is that one in the production these thermoplastic homo- or copolymers instead of bulk polymerization also other polymerization methods known per se, for example solution, suspension or emulsion polymerization, can apply.

Es wurde nun weiterhin gefunden, daß die Ester tertiärer Alkohole der Fumarsäure in bezug auf ihre Polymerisationsgeschwindigkeit den Fumarsäureestern primärer und sekundärer Alkohole außerordentlich überlegen sind. Bei dieser äußerst rasch verlaufenden Polymerisation werden vorzügliche harte farblose"Polymerisäte erhalten, da bei dieser Polymerisation auch der Polymerisationsgrad günstig beeinflußt wird".It has now also been found that the esters of tertiary alcohols of fumaric acid with respect to their The rate of polymerization of the fumaric acid esters of primary and secondary alcohols is extraordinary are superior. This extremely rapid polymerization results in excellent hard colorless "polymerizate obtained, since this Polymerization also has a beneficial effect on the degree of polymerization ".

Die Polymerisation kann in beliebiger Weise nach an sich bekannten Polymerisationsmethoden, z. B.The polymerization can be carried out in any way according to polymerization methods known per se, for. B.

ίο nach der Substanz- bzw. Masse-, Lösungs-, Suspensions- oder Emulsionspolymerisation, erfolgen. Die tertiären Ester der Fumarsäure werden nach dem Verfahren des Hauptpatents 1176 871 und der Zusatzpatentanmeldung 1520 702 sowohl für sich allein polymerisiert als auch mit anderen polymerisationsfähigen Monomeren copolymerisiert.ίο according to the substance or mass, solution, suspension or emulsion polymerization. The tertiary esters of fumaric acid are after Procedure of the main patent 1176 871 and the additional patent application 1520 702 both on their own polymerized as well as copolymerized with other polymerizable monomers.

Die Überlegenheit der Fumarsäureester tertiärer Alkohole in bezug auf die Polymerisationsgeschwindigkeit sei an Hand des nachfolgenden Vergleichsbeispiels näher erläutert.The superiority of the fumaric acid esters of tertiary alcohols with regard to the rate of polymerization will be explained in more detail with reference to the following comparative example.

Beispielexample

Nach dem Verfahren der Polymerisation in Substanz werden folgende Ester in Gegenwart von l°/o Benzoylperoxyd (in Form einer 5O°/oigen Paste) bei einer Temperatur von 72° C polymerisiert: ""' According to the bulk polymerization process, the following esters are polymerized in the presence of 1% benzoyl peroxide (in the form of a 50% paste) at a temperature of 72 ° C: ""'

1. Fumarsäure=di-n-butylester,1. Fumaric acid = di-n-butyl ester,

2. Fumarsäure-di-isobutylester,
3. Fumarsäure-di-sek.-butylester,2. Fumaric acid di-isobutyl ester,
3. Fumaric acid di-sec-butyl ester,

4. Fumarsäure-di-tert.-butylester.4. Di-tert-butyl fumarate.

Folgende Ergebnisse werden erhalten:
Ester 1 und 2 .. nach 100 Stunden viskos,
Ester 3 nach 8 Stunden hartes farblosesThe following results are obtained:
Ester 1 and 2 .. viscous after 100 hours,
Ester 3 after 8 hours hard colorless

Polymerisat,
Ester 4 nach 1 Stunde hartes farblosesPolymer,
Ester 4 hard colorless after 1 hour

Polymerisat.Polymer.

Claims (1)

i 520 703i 520 703 Patentanspruch:Claim: Abänderung der Verfahren des Hauptpatents 1176 871 und der Zusatzpatentanmeldung 1520 702 zur Herstellung thermoplastischer Homo- und Copolymerisate unter Verwendung von Fumarsäureestern sekundärer Alkohole durch Polymerisation in Masse oder anderen an sich bekannten Polymerisationsmethoden in Gegenwart radikalbildender Katalysatoren, dadurch gekennzeichnet, daß an Stelle von Fumarsäureestern sekundärer Alkohole die Fumarsäureester tertiärer Alkohole verwendet werden.Modification of the procedures of the main patent 1176 871 and the additional patent application 1520 702 for the production of thermoplastic homo- and copolymers using of fumaric acid esters of secondary alcohols by polymerization in bulk or other per se known polymerization methods in the presence of radical-forming catalysts, thereby characterized in that, instead of fumaric acid esters of secondary alcohols, fumaric acid esters tertiary alcohols can be used.
DE1964R0038235 1963-01-18 1964-06-27 PROCESS FOR THE MANUFACTURING OF THERMOPLASTIC HOMOPOLYMERIZED OR COPOLYMERIZED PRODUCTS USING FUMAR ACID ESTERS Granted DE1520703B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE1964R0038235 DE1520703B2 (en) 1963-01-18 1964-06-27 PROCESS FOR THE MANUFACTURING OF THERMOPLASTIC HOMOPOLYMERIZED OR COPOLYMERIZED PRODUCTS USING FUMAR ACID ESTERS

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DER34272A DE1176871B (en) 1963-01-18 1963-01-18 Process for the production of thermoplastic homo- or copolymers using esters ª ‡, ª ‰ -unsaturated dicarboxylic acids
DE1964R0038235 DE1520703B2 (en) 1963-01-18 1964-06-27 PROCESS FOR THE MANUFACTURING OF THERMOPLASTIC HOMOPOLYMERIZED OR COPOLYMERIZED PRODUCTS USING FUMAR ACID ESTERS

Publications (2)

Publication Number Publication Date
DE1520703A1 DE1520703A1 (en) 1969-06-19
DE1520703B2 true DE1520703B2 (en) 1973-04-05

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
DE1964R0038235 Granted DE1520703B2 (en) 1963-01-18 1964-06-27 PROCESS FOR THE MANUFACTURING OF THERMOPLASTIC HOMOPOLYMERIZED OR COPOLYMERIZED PRODUCTS USING FUMAR ACID ESTERS

Country Status (1)

Country Link
DE (1) DE1520703B2 (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"

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
DE1520703A1 (en) 1969-06-19

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Legal Events

Date Code Title Description
SH Request for examination between 03.10.1968 and 22.04.1971
C3 Grant after two publication steps (3rd publication)
E77 Valid patent as to the heymanns-index 1977