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Aminal Protection of Epoxide Monomer Permits the Introduction of Multiple Secondary Amine Moieties at Poly(ethylene glycol)
Author(s) -
Blankenburg Jan,
Frey Holger
Publication year - 2019
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.201900057
Subject(s) - polymer chemistry , polymerization , monomer , ethylene glycol , chemistry , copolymer , glycidyl methacrylate , dispersity , aminal , diethylamine , polymer , organic chemistry
In contrast to acetal groups, aminal moieties are almost unknown in polymer chemistry. The aminal‐protected isopropyl‐hexahydro‐pyrimidine glycidyl amine (PyGA) for the anionic ring‐opening polymerization (AROP) is introduced. The monomer is prepared in a two‐step synthesis and can be polymerized in a well‐controlled manner under AROP conditions. Several poly(ethylene glycol) block and triblock copolymers are synthesized in a molecular weight range from 2 700 to 11 400 g mol −1 with up to 11 mol% PyGA. The molecular weight distributions are monomodal with low dispersity ( Đ = M w / M n ) below 1.2. After the polymerization, the acid‐labile hexahydro‐pyrimidine rings can be conveniently cleaved in acidic media, liberating two secondary amines per PyGA monomer unit. The released 1,3‐diamine functionalities can be addressed via post‐polymerization modification and show complexation of copper(II) ions in aqueous solution. The compounds are promising for water‐soluble catalyst systems, the removal of transition metals from water, and as a building block for complexing polyethers for biomedical application.