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Polymers 2016, 8(3), 64; doi:10.3390/polym8030064

Highly Active Copolymerization of Ethylene and N-Acetyl-O-(ω-Alkenyl)-l-Tyrosine Ethyl Esters Catalyzed by Titanium Complex

1
State Key Laboratory of Chemical Resource Engineering, Key Laboratory of Carbon Fiber and Functional Polymers, Ministry of Education, the College of Material Science and Engineering, Beijing University of Chemical Technology, Beijing 100029, China
2
Lab for Synthetic Resin Research Institution of Petrochemical Technology, China National Petroleum Corporation, Beijing 100083, China
3
Liaoyang Petrochemical Corporation, China National Petroleum Corporation, Liaoyang 111003, China
*
Author to whom correspondence should be addressed.
Academic Editor: Changle Chen
Received: 25 December 2015 / Revised: 18 February 2016 / Accepted: 24 February 2016 / Published: 10 March 2016
(This article belongs to the Special Issue Metal-Mediated Polymer Synthesis)
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Abstract

A series of N-acetyl-O-(ω-alkenyl)-l-tyrosine ethyl esters were synthesized by the reaction of vinyl bromides (4-bromo-1-butene, 6-bromo-1-hexene, 8-bromo-1-octene and 10-bromo-1-decene) with N-acetyl-l-tyrosine ethyl ester. 1H NMR, elemental analysis, FT-IR, and mass spectra were performed for these N-acetyl-O-(ω-alkenyl)-l-tyrosine ethyl esters. The novel titanium complex can catalyze the copolymerization of ethylene and N-acetyl-O-(ω-alkenyl)-l-tyrosine ethyl esters efficiently and the highest catalytic activity was up to 6.86 × 104 gP·(molTi)−1·h−1. The structures and properties of the obtained copolymers were characterized by FT-IR, (1H)13C NMR, GPC, DSC, and water contact angle. The results indicated that the obtained copolymers had a uniformly high average molecular weight of 2.85 × 105 g·mol−1 and a high incorporation ratio of N-acetyl-O-(but-3-enyl)-l-tyrosine ethyl ester of 2.65 mol % within the copolymer chain. The units of the comonomer were isolated within the copolymer chains. The insertion of the polar comonomer into a copolymer chain can effectively improve the hydrophilicity of a copolymer. View Full-Text
Keywords: N-acetyl-O-(ω-alkenyl)-l-tyrosine ethyl esters; titanium complex; copolymerization; hydrophilicity N-acetyl-O-(ω-alkenyl)-l-tyrosine ethyl esters; titanium complex; copolymerization; hydrophilicity
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MDPI and ACS Style

Wang, J.; Li, H.; Zhang, R.; Shi, X.; Yi, J.; Wang, J.; Huang, Q.; Yang, W. Highly Active Copolymerization of Ethylene and N-Acetyl-O-(ω-Alkenyl)-l-Tyrosine Ethyl Esters Catalyzed by Titanium Complex. Polymers 2016, 8, 64.

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