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A Highly Efficient Aromatic Amine Ligand/Copper(I) Chloride Catalyst System for the Synthesis of Poly(2,6-dimethyl-1,4-phenylene ether)

1
School of Chemical Engineering, Sungkyunkwan University, 2066 Seobu-ro, Jangan-gu, Suwon-si, Gyeonggi-do 16419, Korea
2
Hyosung R&D Business Labs, 74 Simin-daero, Dongan-gu, Anyang-si 14080, Gyunggi-do, Korea
3
LG Household & Health Care R&D Center, LG Science Park, Magok, Kangseo-go, Seoul 07795, Korea
4
SAMSUNG SDI, SDI-dong, Maetan-dong 130, Samsung-ro, Yeongtong-gu, Suwon-si, Gyeonggi-do 16678, Korea
5
Hyosung R&D Business Labs, 74 Simin-daero, Dongan-gu, Anyang-si, Gyunggi-do 14080, Korea
*
Author to whom correspondence should be addressed.
Polymers 2018, 10(4), 350; https://doi.org/10.3390/polym10040350
Received: 19 February 2018 / Revised: 18 March 2018 / Accepted: 20 March 2018 / Published: 22 March 2018
(This article belongs to the Special Issue Polymerization Kinetics)
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Abstract

Highly active catalyst systems for polymerizing 2,6-dimethylphenol were studied by using aromatic amine ligands and copper(I) chloride. The aromatic amine ligands employed were pyridine, 1-methylimidazole, 2-aminopyridine, 3-aminopyridine, and 4-aminopyridine. A mixture of chloroform and methanol (9:1, v/v) was used as a polymerization solvent. All experiments were performed with oxygen uptake measurement apparatus, while the reaction rate for each aromatic amine ligand-Cu catalyst system and the amount of by-product, 3,3′,5,5′-Tetramethyl-4,4′diphenoquinone (DPQ), were measured to determine the efficiency of the catalyst systems. The 4-aminopyridine/Cu (I) catalyst system was found to be extremely efficient in poly(2,6-dimethyl-1,4-phenylene ether) (PPE) synthesis; it had the fastest reaction rate of 6.98 × 10−4 mol/L·s and the lowest DPQ production. The relatively high basicity of 4-aminopyridne and the less steric hindrance arising from a coordination of Cu and 4-aminopyridine in this catalyst are responsible for the fast polymerization rate. When 2-aminoprydine (an isomer of 4-aminopyridine) was used as a ligand, however, no polymerization occurred probably due to steric hindrance. View Full-Text
Keywords: rate of polymerization; aromatic amine ligand; highly effective catalyst; copper(I) chloride; poly(2,6-dimethyl-1,4-phenylene ether); 3,3′,5,5′-tetramethyl-4,4′diphenoquinone rate of polymerization; aromatic amine ligand; highly effective catalyst; copper(I) chloride; poly(2,6-dimethyl-1,4-phenylene ether); 3,3′,5,5′-tetramethyl-4,4′diphenoquinone
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Kim, K.; Shin, M.J.; Kim, Y.T.; Kim, J.-I.; Kim, Y.J. A Highly Efficient Aromatic Amine Ligand/Copper(I) Chloride Catalyst System for the Synthesis of Poly(2,6-dimethyl-1,4-phenylene ether). Polymers 2018, 10, 350.

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