Related Experiment Video
Updated: Jan 27, 2026

Generation of Size-controlled Poly ethylene Glycol Diacrylate Droplets via Semi-3-Dimensional Flow Focusing Microfluidic Devices
Published on: July 3, 2018
Aminal Protection of Epoxide Monomer Permits the Introduction of Multiple Secondary Amine Moieties at Poly(ethylene
Jan Blankenburg1,2, Holger Frey1
1Institute of Organic Chemistry, Johannes Gutenberg University, Duesbergweg 10-14, 55128, Mainz, Germany.
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 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.
More Related Videos
Related Concept Videos
Nomenclature of Secondary and Tertiary Amines
Amines: Introduction
Protecting Groups for Aldehydes and Ketones: Introduction
Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
Sharpless Epoxidation
Collisions in Multiple Dimensions: Introduction

