Synthesis of quaternary ammonium ion-grafted polyolefins via activation of inert C----H bonds and nitroxide mediated radical polymerization

A TEMPO-functionalized isotactic poly(1-butene) macroinitiator was synthesized via rhodium-catalyzed activation of the alkane C---H bonds in polyolefin side chain using a boron reagent and subsequent transformations of the boronate ester group in the polymer. These functionalization processes did no...

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Published in:	Journal of polymer science. Part A, Polymer chemistry Vol. 47; no. 18; pp. 4519 - 4531
Main Authors:	Jo, Tae Soo, Yang, Meilong, Brownell, Lacie V, Bae, Chulsung
Format:	Journal Article
Language:	English
Published:	Hoboken Wiley Subscription Services, Inc., A Wiley Company 15-09-2009 Wiley
Subjects:	Applied sciences Exact sciences and technology functionalization of polymers graft copolymers macromonomers modification Organic polymers Physicochemistry of polymers Polymerization polyolefins Preparation, kinetics, thermodynamics, mechanism and catalysts stereospecific polymers Graft copolymer Quaternization graft copolymers Quaternary ammonium copolymer Composition effect Styrene derivative copolymer Grafting Thermal stability Wettability Functionalization Styrene derivatives Isotactic polymer Piperidine derivatives functionalization of polymers Surface properties stereospecific polymers Tosylation Amine copolymer Boron compound Butene derivative copolymer Condensation reaction Nitroxyl Hydroxylation Butylene derivative copolymer Butylene polymer macromonomers Experimental study Functional polymer modification Radical catalyst Chemical modification Initiator polymer Free radical polymerization polyolefins Preparation Tertiary amine Phenols
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Summary:	A TEMPO-functionalized isotactic poly(1-butene) macroinitiator was synthesized via rhodium-catalyzed activation of the alkane C---H bonds in polyolefin side chain using a boron reagent and subsequent transformations of the boronate ester group in the polymer. These functionalization processes did not induce cross-linking or degradation of the polymer chains. Nitroxide mediated radical polymerization of dipropyl(4-vinylphenyl)amine with the macroinitiator produced high-molecular weight amine-grafted copolymers of the polyolefin. Adjusting the ratio of polar monomer concentration to macroinitiator concentration controlled the concentrations of amine blocks in the graft copolymers up to 10 mol %. Quaternization of the amine-grafted copolymers with methyl triflate generated ammonium ion blocks along the side chain of the graft copolymers. A systematic decrease of contact angle in a series of ammonium ion-grafted copolymers was observed through water contact angle measurements, suggesting that the graft polymerization and the quaternization led to increased hydrophilicity in the polymers.
Bibliography:	http://dx.doi.org/10.1002/pola.23505 Meilong Yang is the visiting undergraduate student from Stanford University. ObjectType-Article-2 SourceType-Scholarly Journals-1 ObjectType-Feature-1 content type line 23
ISSN:	0887-624X 1099-0518
DOI:	10.1002/pola.23505