Poly(methylene amine): A Polymer with the Maximum Possible Number of Amino Groups on a Polymer Backbone

Abstract

One of the most demanding challenges in research is exploring the theoretical limits of properties. A good example of these limitations comes from polymers containing many amino functions on the polymer backbone. These polymers have become increasingly important in industrial applications, which make use of their ability to form stable amino-

One-pot domino synthesis of polyvicinalamine monomers

“…Polyamines have received much interest in view of their high amino group content, multi-interaction modes, facile tailorability and widespread applicability in products ranging from commodity chemicals for pulp processing or water treatment to specialty chemicals intended for use in pharmacy and biotechnology. [1][2][3] Scheme 1. Polyamine featuring a 1:1 nitrogen-to-carbon ratio.…”

“…Of the three approaches portrayed (Scheme 2), the monomers utilized have been based on butenedioic acid, cis-1,2-diamidoethene, and 1,3-diacetyl-4-imidazolin-2-one. [1][2][3][4][5][6][7][8][9][10][11][12][13] The use of commercial butenedioic acid type monomers (Scheme 2, top left) introduces inconveniences related to halogenation, corrosion control and waste management. The use of cis-1,2-diamidoethene monomers (Scheme 2, top right) permits a relatively simpler, greener industrial process.…”

“…Still, neither approach has enabled the formation of high molecular weight polyvicinalamines. [2][3][4][5] The polymerization of 1,3-diacetyl-4-imidazolin-2-one (Scheme 2, bottom left) has yielded comparatively higher molecular weight materials. 2,4 This last monomer, a cyclic analogue of cis-1,2-di(acetamido)ethene (1a, Entry 1 in Table 1), is highly reactive by virtue of the ring structure, which limits steric clutter about the double bond, and the acetyl groups, which overcome limitations inherent to polymerizing 4-imidazolin-2-one.…”

“…2,4 This last monomer, a cyclic analogue of cis-1,2-di(acetamido)ethene (1a, Entry 1 in Table 1), is highly reactive by virtue of the ring structure, which limits steric clutter about the double bond, and the acetyl groups, which overcome limitations inherent to polymerizing 4-imidazolin-2-one. 3 Still, the high hydrolytic stability of the polymeric intermediate formed demands harsh conditions to generate the free polyvicinalamine. 3 Scheme 2.…”

“…3 Still, the high hydrolytic stability of the polymeric intermediate formed demands harsh conditions to generate the free polyvicinalamine. 3 Scheme 2. Monomers to prepare oligo-and polyvicinalamines: Butenedioic acid and derivatives (top, left); cis-1,2-diamidoethene (top, right); and 1,3-diacetyl-4-imidazolin-2-one (bottom, left).…”