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A New Self‐Polymerization of Acrylic Acid with a Mono‐Aziridine Containing Compound
Author(s) -
Chen PoCheng,
Wang ShihChieh,
Hwang JingZhong,
Yeh JenTaut,
Huang ChiYuan,
Chen KanNan
Publication year - 2010
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201000125
Subject(s) - chemistry , aziridine , polymerization , polymer chemistry , acrylic acid , polymer , solution polymerization , cationic polymerization , chain growth polymerization , ionic polymerization , solvent , radical polymerization , organic chemistry , monomer , ring (chemistry)
A new self‐polymerization took place between acrylic acid (AA) and a mono‐aziridine containing compound, e.g. methyl 3‐(aziridin‐1‐yl) propanoate (MAP) upon mixing that resulted in formation of a linear polyethyleneimine (PEI) with amino‐ester bonds. This self‐polymerization has a key reaction of ring opening reaction occurred between carboxylic acid and aziridine that led to an amino‐ester bond formation. The model reactions of trimethylacetic acid (TMAA) with MAP and then with ethyl acrylate (EA) were designed to demonstrat the self‐polymerization mechanism. The model reaction product at each stage related to that of polymerization was characterized by FT‐IR and FT‐NMR. The self‐polymerization occurred via three consecutive reactions at ambient temperature, which were acid‐base neutralization, aziridine ring‐opening and finally Michael addition reaction. Their average molecular weight of resulting PEI could be over 60,000 in aqueous medium or a higher polymer formation in bulk, which is insoluble in water or any organic solvent. This self‐polymerization process could have potential for adhesives, composite materials or other polymer applications.