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- Title
Aminal Protection of Epoxide Monomer Permits the Introduction of Multiple Secondary Amine Moieties at Poly(ethylene glycol).
- Authors
Blankenburg, Jan; Frey, Holger
- Abstract
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 = Mw/Mn) below 1.2. After the polymerization, the acid-labile hexahydropyrimidine 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.
- Subjects
SECONDARY amines; MONOMERS; RING-opening polymerization; BLOCK copolymers; MOLECULAR weights; ETHYLENE glycol
- Publication
Macromolecular Rapid Communications, 2019, Vol 40, Issue 12, p1
- ISSN
1022-1336
- Publication type
Article
- DOI
10.1002/marc.201900057