Alternating copolymerization and terpolymerization of vinyl-substituted phenolic antioxidants with propene and carbon monoxide by a palladium(II)-based catalyst

Polyketones containing intramolecular stabilizers

Markku Auer, Mika Kettunen, Adnan S. Abu-Surrah (Corresponding Author), Markku Leskelä, Carl-Eric Wilen

Research output: Contribution to journalArticleScientificpeer-review

9 Citations (Scopus)

Abstract

The copolymerization and terpolymerization reactions of the vinyl‐substituted phenolic stabilizers, 6‐tert‐butyl‐2‐(1,1‐dimethylhept‐6‐enyl)‐4‐methylphenol, o‐allylphenol, 4‐methylstyrene‐2,6‐di‐tert‐butylphenol and 2,6‐di‐tert‐butyl‐4‐allylphenol, with propene and carbon monoxide, by using the solvent‐stabilized palladium(II) phosphine complex [Pd(dppp)(NCCH3)2](BF4)2 (dppp, 1,3‐bis(diphenylphosphino)propane) as a catalyst precursor and methanol as a co‐catalyst, is described. The influence of functional α‐olefins/CO units, distributed statistically along the propene/carbon monoxide (P/CO) copolymer backbone, on the molecular weight, glass transition temperature (Tg), elastic behavior and stability of the high‐molecular‐weight P/CO copolymer has been investigated. Loss of both elasticity and transparency were observed upon incorporating o‐allylphenol as a termonomer. The terpolymers, which contain phenolic stabilizers, were shown to be more stable when compared to the stabilizer‐free polyketones. In contrast to the propene/carbon monoxide copolymer, no degradation was observed for the 2,6‐di‐tert‐butyl‐4‐allylphenol/P/CO terpolymer; instead, the molar masses increased.
Original languageEnglish
Pages (from-to)2015 - 2019
Number of pages5
JournalPolymer International
Volume53
Issue number12
DOIs
Publication statusPublished - 2004
MoE publication typeA1 Journal article-refereed

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Terpolymerization
Stabilizers (agents)
Palladium
Carbon Monoxide
Antioxidants
Carbon monoxide
Copolymerization
Propylene
Catalysts
Terpolymers
Copolymers
Propane
phosphine
Molar mass
Transparency
Olefins
Alkenes
Elasticity
Methanol
Molecular weight

Cite this

@article{bc4b21b9c66848b9887d6518ebc4cfed,
title = "Alternating copolymerization and terpolymerization of vinyl-substituted phenolic antioxidants with propene and carbon monoxide by a palladium(II)-based catalyst: Polyketones containing intramolecular stabilizers",
abstract = "The copolymerization and terpolymerization reactions of the vinyl‐substituted phenolic stabilizers, 6‐tert‐butyl‐2‐(1,1‐dimethylhept‐6‐enyl)‐4‐methylphenol, o‐allylphenol, 4‐methylstyrene‐2,6‐di‐tert‐butylphenol and 2,6‐di‐tert‐butyl‐4‐allylphenol, with propene and carbon monoxide, by using the solvent‐stabilized palladium(II) phosphine complex [Pd(dppp)(NCCH3)2](BF4)2 (dppp, 1,3‐bis(diphenylphosphino)propane) as a catalyst precursor and methanol as a co‐catalyst, is described. The influence of functional α‐olefins/CO units, distributed statistically along the propene/carbon monoxide (P/CO) copolymer backbone, on the molecular weight, glass transition temperature (Tg), elastic behavior and stability of the high‐molecular‐weight P/CO copolymer has been investigated. Loss of both elasticity and transparency were observed upon incorporating o‐allylphenol as a termonomer. The terpolymers, which contain phenolic stabilizers, were shown to be more stable when compared to the stabilizer‐free polyketones. In contrast to the propene/carbon monoxide copolymer, no degradation was observed for the 2,6‐di‐tert‐butyl‐4‐allylphenol/P/CO terpolymer; instead, the molar masses increased.",
author = "Markku Auer and Mika Kettunen and Abu-Surrah, {Adnan S.} and Markku Leskel{\"a} and Carl-Eric Wilen",
year = "2004",
doi = "10.1002/pi.1617",
language = "English",
volume = "53",
pages = "2015 -- 2019",
journal = "Polymer International",
issn = "0959-8103",
publisher = "Wiley",
number = "12",

}

Alternating copolymerization and terpolymerization of vinyl-substituted phenolic antioxidants with propene and carbon monoxide by a palladium(II)-based catalyst : Polyketones containing intramolecular stabilizers. / Auer, Markku; Kettunen, Mika; Abu-Surrah, Adnan S. (Corresponding Author); Leskelä, Markku; Wilen, Carl-Eric.

In: Polymer International, Vol. 53, No. 12, 2004, p. 2015 - 2019.

Research output: Contribution to journalArticleScientificpeer-review

TY - JOUR

T1 - Alternating copolymerization and terpolymerization of vinyl-substituted phenolic antioxidants with propene and carbon monoxide by a palladium(II)-based catalyst

T2 - Polyketones containing intramolecular stabilizers

AU - Auer, Markku

AU - Kettunen, Mika

AU - Abu-Surrah, Adnan S.

AU - Leskelä, Markku

AU - Wilen, Carl-Eric

PY - 2004

Y1 - 2004

N2 - The copolymerization and terpolymerization reactions of the vinyl‐substituted phenolic stabilizers, 6‐tert‐butyl‐2‐(1,1‐dimethylhept‐6‐enyl)‐4‐methylphenol, o‐allylphenol, 4‐methylstyrene‐2,6‐di‐tert‐butylphenol and 2,6‐di‐tert‐butyl‐4‐allylphenol, with propene and carbon monoxide, by using the solvent‐stabilized palladium(II) phosphine complex [Pd(dppp)(NCCH3)2](BF4)2 (dppp, 1,3‐bis(diphenylphosphino)propane) as a catalyst precursor and methanol as a co‐catalyst, is described. The influence of functional α‐olefins/CO units, distributed statistically along the propene/carbon monoxide (P/CO) copolymer backbone, on the molecular weight, glass transition temperature (Tg), elastic behavior and stability of the high‐molecular‐weight P/CO copolymer has been investigated. Loss of both elasticity and transparency were observed upon incorporating o‐allylphenol as a termonomer. The terpolymers, which contain phenolic stabilizers, were shown to be more stable when compared to the stabilizer‐free polyketones. In contrast to the propene/carbon monoxide copolymer, no degradation was observed for the 2,6‐di‐tert‐butyl‐4‐allylphenol/P/CO terpolymer; instead, the molar masses increased.

AB - The copolymerization and terpolymerization reactions of the vinyl‐substituted phenolic stabilizers, 6‐tert‐butyl‐2‐(1,1‐dimethylhept‐6‐enyl)‐4‐methylphenol, o‐allylphenol, 4‐methylstyrene‐2,6‐di‐tert‐butylphenol and 2,6‐di‐tert‐butyl‐4‐allylphenol, with propene and carbon monoxide, by using the solvent‐stabilized palladium(II) phosphine complex [Pd(dppp)(NCCH3)2](BF4)2 (dppp, 1,3‐bis(diphenylphosphino)propane) as a catalyst precursor and methanol as a co‐catalyst, is described. The influence of functional α‐olefins/CO units, distributed statistically along the propene/carbon monoxide (P/CO) copolymer backbone, on the molecular weight, glass transition temperature (Tg), elastic behavior and stability of the high‐molecular‐weight P/CO copolymer has been investigated. Loss of both elasticity and transparency were observed upon incorporating o‐allylphenol as a termonomer. The terpolymers, which contain phenolic stabilizers, were shown to be more stable when compared to the stabilizer‐free polyketones. In contrast to the propene/carbon monoxide copolymer, no degradation was observed for the 2,6‐di‐tert‐butyl‐4‐allylphenol/P/CO terpolymer; instead, the molar masses increased.

U2 - 10.1002/pi.1617

DO - 10.1002/pi.1617

M3 - Article

VL - 53

SP - 2015

EP - 2019

JO - Polymer International

JF - Polymer International

SN - 0959-8103

IS - 12

ER -