Ethylene‐propylene terpolymers with conjugated double bonds

Sonnenfeld, R. J.; Kahle, G. R.; Buck, O.

doi:10.1002/app.1969.070130209

J of Applied Polymer Sci

1969

DOI: 10.1002/app.1969.070130209

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Ethylene‐propylene terpolymers with conjugated double bonds

R. J. Sonnenfeld¹,

G. R. Kahle²,

O. Buck³

Abstract: synopsisA study was made of ethylenepropylene terpolymerization with fulvenes and various acetylenes. Vinylacetylene, %methyl-1-buten-3-yne (isopropenyl-acetylene) or 6,6dimethylfulvene in conjunction with ethylene and propylene formed terpolymers which contained conjugated double bonds. The presence of conjugated double bonds was established by infrared and ultraviolet analyses. The terpolymers were randomly unsaturated with sufficient unsaturation to be sulfur-vulcanized.

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1974

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Cited by 8 publications

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Recent developments in synthetic elastomers

Schroeder

1971

Angew. Makromol. Chem.

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This paper reviews the changes which have occurred from 1965 to 1970 in synthetic elastomers, principally from the view of new products, emphasizing the scientific trends involved. Subjects covered include diene rubbers, ethylene/propylene copolymers and particularly the various specialty type elastomers, including liquid and thermoplastic block copolymers. The trend towards precise control of elastomer structure and of monomer sequence, configuration, and orientation in the growing chain is emphasized. ZUSAMMENFASSUNG :Diese Veroffentlichung beschreibt zusammenfassend die hderungen, die auf d:m Gebiet der synthetischen Elastomeren von 1965-1970 stattgefunden haben, vorwiegend im Hinblick auf neue Produkte und mit besonderer Betonung der damit verbundenen wissenschaftlichen Entwicklungsrichtungen. Unter anderem werden die Gebiete der Dien-Kautschuke, bthylen/Propylen-Copolymere und besonders verschiedene Sondertypen von Elastomeren, einschliefllich flussiger und thermoplastischer Block-Copolymere erortert. Das Bestreben, die Struktur des Elastomeren sowie Monomerenfolge, Konfiguration und Orientierung der wachsenden Kette genau zu kontrollieren, wird betont.

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Recent developments in synthetic elastomers

Schroeder

1971

Angew. Makromol. Chem.

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The polymerization, copolymerization and terpolymerization of 1‐isopropylidene‐3a.4.7.7a‐tetrahydroindene by anionic coordinate, radical and anionic catalysts

et al. 1970

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By means of vanadium based anionic coordinate catalysts l-isopropylidene-3a.4.7.7atetrahydroindene (I) can be terpolymerized with ethylene and propylene and copolymerized with ethylene. IR, NMR, UV spectroscopic data, and mol. wt. distributions are reported for the polymers.The incorporation of I is predominantly by opening of the cyclohexene double bond. The content of I was generally less than 10 mole-yo.Attempts to obtain homopolymers of I and copolymers of propylene and I with this type of catalyst were unsuccessfull.No solid polymer could be produced from I by free radical or anionic catalysts. With AIBN only oligomers were obtained which had cyanoisobutyric groups attached to the conjugated double bond system. K or KNHz in ammonia solution react with I in equimolar ratios to give waxy products which do not contain NHz groups. With K di-hydrogenated derivatives of I are formed. The results have been interpreted in terms of stabilized radicals and anions derived from I which are unable to propagate. ZUSAMMENFASSUNG: l-Isopropyliden-3a.4.7.7a-tetrahydroinden (I) kann mit Athylen und Propylen durch anionisch-koordinative Vanadin-Katalysatoren terpolymerisiert und mit Bthylen copolymerisiert werden. Fur die Polymeren werden die IR-, NMR-und UV-spektroskopischen Daten sowie die Molekulargewichtsverteilungen mitgeteilt. Der Einbau von I verlauft hauptsachlich uber die Offnung der Cyclohexendoppelbindung. I m allgemeinen betragt der Gehalt an I weniger als 10 M01-y~. Versuche, Homopolymere von I und Copolymere aus Propylen und I mit diesem Katalysatortyp zu erhalten, waren ohne Erfolg. Mit radikalischen oder mit anionischen Katalysatoren konnte aus I kein festes Polymeres erhalten werden. Lediglich mit AIBN wurden Oligomere erhalten, die Isobuttersaurenitrilgruppen, gebunden an das System der konjugierten Doppelbindungen, enthielten. In fliissigem Ammoniak gelost, reagiert K oder KNHz mit I in aquimolekularen Mengen zu wachsartigen Produkten, die keine NHz-Gruppen enthalten. Mit K werden Dihydroderivate von I gebildet. Die Ergebnisse lassen sich durch die Annahme erklaren, daB sich aus I stabi!isierte Radikale und Anionen bilden, die nicht zum Wachstum befahigt sind.

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Ethylene‐propylene based terpolymers containing tricyclo[5.2.1.0^2,6]deca‐2,5,8‐triene

et al. 1974

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Tricyclo[5.2.1 .O'."]deca-2,5,8-triene ( I ) (trivial name: dehydro-isodicyc1opentadiene)or a mixture of its methyl derivatives were used as termonomers to obtain ethylene-propylenetriene terpolymers (EPTM's) having unusual properties in the curing process, even at low levels of triene (ca. 1 wt-'Y"). Three types of catalyst systems have been investigated, i. e. based on VCI4, VO[O(CHz),C'H.3].3, or V(acac), and (C2H5)2A1CI. Several parameters of the terpolymerization process were studied (e.g. Al/V mole ratio; catalyst and termonomer concentration; polymerization time; presence of a Lewis base or chain transfer agent) and their influence on M , and EPTM composition were evaluated.Fractionation data and the use of model compounds allow to conclude that 1 enters EPTM chains randomly and by selective opening of the norbornenic double bond, whereas the conjugated diene system is involved in side-reactions if the catalyst has some acid character or the concentration of the triene is above some critical values. ZUSAMMENFASSUNG: Tricyclo[5.2. I .02.b]deca-2,5,8-trien( I ) (Trivialname: Dehydro-isodicyclopentadien) oder eine Mischung seiner Methylderivate wurden verwendet als Termonomere zur Herstellung von Athylen-Propylen-Trien Terpolymeren (EPTM) mit ungewohnlichen Eigenschaften beim VulkanisationsprozeD, selbst bei niedrigem Triengehalt (etwa I Gew.-x). Drei Arten von Katalysatorsystemen wurden untersucht, und zwar auf der Basis von VC14,VO[O(CH2)3CH3]3 oder V(acac)3 und (C2H5)zA1CI. Es wurden mehrere Parameter des Terpolymerisationsverfahrens untersucht (z. B. AljV Molverhaltnis; Katalysator und Termonomerkonzentration; Polymerisationsdauer; Anwesenheit einer Lewisbase oder eines Ketteniibertragungsmittels) und ihre Wirkung auf M , und die Zusammensetzung von EPTM ausgewertet. Die Fraktionierungsangaben und die Anwendung von Modellverbindungen fiihren zu dem SchluD, dal3 1 in die EPTM-Ketten statistisch und durch selektives Offnen der norbornenischen Doppelbindung eintritt, wahrend das konjugierte Diensystem Nebenreaktionen eingeht, wenn der Katalysator einen sauren Charakter aufweist oder die Trienkonzentration eine kritische Konzentration iibersteigt.

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Ethylene‐propylene terpolymers with conjugated double bonds

Cited by 8 publications

References 2 publications

Recent developments in synthetic elastomers

Recent developments in synthetic elastomers

The polymerization, copolymerization and terpolymerization of 1‐isopropylidene‐3a.4.7.7a‐tetrahydroindene by anionic coordinate, radical and anionic catalysts

Ethylene‐propylene based terpolymers containing tricyclo[5.2.1.0^2,6]deca‐2,5,8‐triene

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About

Ethylene‐propylene terpolymers with conjugated double bonds

Cited by 8 publications

References 2 publications

Recent developments in synthetic elastomers

Recent developments in synthetic elastomers

The polymerization, copolymerization and terpolymerization of 1‐isopropylidene‐3a.4.7.7a‐tetrahydroindene by anionic coordinate, radical and anionic catalysts

Ethylene‐propylene based terpolymers containing tricyclo[5.2.1.02,6]deca‐2,5,8‐triene

Contact Info

Product

Resources

About

Ethylene‐propylene based terpolymers containing tricyclo[5.2.1.0^2,6]deca‐2,5,8‐triene