AT214643B - Process for the polymerization of organic, unsaturated compounds - Google Patents
Process for the polymerization of organic, unsaturated compoundsInfo
- Publication number
- AT214643B AT214643B AT25260A AT25260A AT214643B AT 214643 B AT214643 B AT 214643B AT 25260 A AT25260 A AT 25260A AT 25260 A AT25260 A AT 25260A AT 214643 B AT214643 B AT 214643B
- Authority
- AT
- Austria
- Prior art keywords
- polymerization
- organic
- acid esters
- unsaturated compounds
- unsaturated compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000006116 polymerization reaction Methods 0.000 title claims description 11
- 150000001875 compounds Chemical class 0.000 title claims description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- -1 peroxycarboxylic acid ester Chemical class 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 239000002253 acid Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- SCKXCAADGDQQCS-UHFFFAOYSA-N Performic acid Chemical class OOC=O SCKXCAADGDQQCS-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 238000012644 addition polymerization Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Polymerization Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Polymerisation organischer, ungesättigter
Verbindungen
Die Erfindung betrifft ein Verfahren zur Polymerisation organischer, ungesättigter Verbindungen unter Verwendung neuer Peroxycarbonsäureester, die als freie Radikale freisetzende Katalysatoren oder Initiatoren in Additionspolymerisationsverfahren verwendet werden können.
Bekannt sind Peroxydicarbonsäureester, Monoperoxycarbonsäureester und Diperoxycarbonsäureester der allgemeinen Formeln
EMI1.1
und
EMI1.2
von denen einige, insbesondere Peroxydicarbonsäureester, als Katalysatoren zur Polymerisation von Vinylestern und Äthylen verwendet werden. Obgleich Peroxydicarbonsäureester für diesen Zweck verwendbar sind, ist dies ; infolge ihrer Löslichkeit und ihrer spezifischen Wärmestabilität, nur in beschränktem Ausmass möglich, da diese Verbindungen in Mineralölen und ähnlichen kohlenwasserstoffhaltigen Lösungsmitteln zu wenig löslich sind, um ohne Bedenken in Lösung bei tiefen Temperaturen eingesetzt werden zu können, und sie bei höheren Temperaturen, bei welchen sie löslich sind, leicht zersetzt werden können.
Es wurde nunmehr eine neue Gruppe von Peroxycarbonsäureestern gefunden, die bessere Löslichkeiten aufweisen, die ferner Polymerisationsverfahren, in denen sie als Katalysatoren eingesetzt sind, nicht etwa auf Grund ihrer Instabilität komplizieren und die schliesslich günstige Polymerisationsgeschwindigkeiten in Temperaturbereichen erzielen lassen, bei welchen solche Geschwindigkeiten bei Verwendung bekannter Katalysatoren nicht leicht erreicht werden können.
Gemäss vorliegender Erfindung wird ein Verfahren zur Herstellung von Polymeren angegeben, nach welchem eine Verbindung, welche die Gruppe C=CH enthält. Polymerisationsbedingungen in Gegenwart einer katalytischen Menge eines Peroxycarbonsäureesters unterworfen wird, das darin besteht, dass die Polymerisation der ungesättigten Verbindung unter Verwendung eines Acylperoxycärbonsäureesters der allgemeinen Formel
EMI1.3
<Desc/Clms Page number 2>
durchgeführt wird, in welcher R und R'substituierte oder nichtsubstituierte Kohlenwasserstoffreste darstellen.
Zu Verbindungen, die gemäss diesem Verfahren polymerisiert werden können, zählen Äthylen, Styrol, Methylmethacrylat, Vinylchlorid, Vinylacetat und andere Vinylester sowie ähnliche Verbindungen. Die Acylperoxycarbonsäureester eignen sich besonders gut als Katalysatoren zur Polymerisation von Äthylen.
Die Acylperoxycarbonsäureester können durch Umsetzung einer Peroxycarbonsäure der allgemeinen Formel
EMI2.1
mit einem Halogenformiat der allgemeinen Formel
EMI2.2
EMI2.3
<Desc/Clms Page number 3>
EMI3.1
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the polymerization of organic, unsaturated
links
The invention relates to a process for the polymerization of organic, unsaturated compounds using new peroxycarboxylic acid esters which can be used as catalysts or initiators that release free radicals in addition polymerization processes.
Peroxydicarboxylic acid esters, monoperoxycarboxylic acid esters and diperoxycarboxylic acid esters of the general formulas are known
EMI1.1
and
EMI1.2
some of which, especially peroxydicarboxylic acid esters, are used as catalysts for the polymerization of vinyl esters and ethylene. While peroxydicarboxylic acid esters are useful for this purpose, this is; Due to their solubility and their specific heat stability, only possible to a limited extent, since these compounds are too insoluble in mineral oils and similar hydrocarbon-containing solvents to be able to be used in solution at low temperatures without hesitation, and they at higher temperatures at which they are soluble, can be easily decomposed.
A new group of peroxycarboxylic acid esters has now been found which have better solubilities, which further complicate polymerization processes in which they are used as catalysts, not because of their instability, and which ultimately allow favorable polymerization rates to be achieved in temperature ranges at which such rates are used known catalysts cannot be easily achieved.
According to the present invention, a process for the production of polymers is specified, according to which a compound which contains the group C = CH. Is subjected to polymerization conditions in the presence of a catalytic amount of a peroxycarboxylic acid ester, which consists in that the polymerization of the unsaturated compound using an acyl peroxycarboxylic acid ester of the general formula
EMI1.3
<Desc / Clms Page number 2>
is carried out, in which R and R 'represent substituted or unsubstituted hydrocarbon radicals.
Compounds that can be polymerized according to this process include ethylene, styrene, methyl methacrylate, vinyl chloride, vinyl acetate and other vinyl esters and similar compounds. The acyl peroxycarboxylic acid esters are particularly suitable as catalysts for the polymerization of ethylene.
The acylperoxycarboxylic acid esters can be obtained by reacting a peroxycarboxylic acid of the general formula
EMI2.1
with a haloformate of the general formula
EMI2.2
EMI2.3
<Desc / Clms Page number 3>
EMI3.1
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB214643X | 1959-01-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT214643B true AT214643B (en) | 1961-04-25 |
Family
ID=10163378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT25260A AT214643B (en) | 1959-01-16 | 1960-01-14 | Process for the polymerization of organic, unsaturated compounds |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT214643B (en) |
-
1960
- 1960-01-14 AT AT25260A patent/AT214643B/en active
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