Functional Polymers Bearing Reactive Azetidinium Groups: Synthesis and Characterization

Abstract

Functional polymers with azetidinium groups in the backbone are synthesized via the reaction of aminotelechelic polymers, containing primary and secondary amino groups, with epichlorohydrin. During the reaction, the secondary amino groups are transformed into azetidinium groups and the primary amino groups are transformed into amino-chlorohydrin, amino-epoxide, and azetidinium groups. The formation of desired functional groups in the polymer is controlled by tuning the reaction conditions. To understand the infl uence of reaction conditions generating the desired functional groups, model reactions of primary and secondary amines with epichlorohydrin are studied in detail, including the infl uence of the mole ratio of the starting materials, effect of solvent, effect of pH, and reaction kinetics. high binding capacity of Hercosett 125 due to its ionic nature and cross linking ability, as the four membered strained rings can react with free secondary amino groups of the polymeric resin. The main disadvantage of Hercosett 125 is its low stability. The polymer can be handled only in solution; once the solvent is removed crosslinking occurs. This problem can be solved by synthesizing polymers containing a lower concentration of azetidinium groups in the chain compared to Hercosett 125 and, in addition, hydrophobic segments. Research was started with a hydrophobic polymer containing two primary and a secondary amino groups (Scheme 2 ).These polymers are expected to absorb strongly on a wide range of substrates due to two type of interactions: i) Ionic interactions. It is believed that the cationic azetidinium moiety, which is expected to be formed in the reaction of the secondary amino groups with epichlorohydrin, interacts with the negatively charged surface of the substrate. ii) Hydrophobic interactions. The hydrophobic polymer backbone is responsible for the interaction with hydrophobic domains of the substrate.The main problem for the synthesis of the above designed polymers is the lack of selectivity for the

Azetidinium Functionalized Polytetrahydrofurans: Antimicrobial Properties in Solution and Application to Prepare Non Leaching Antimicrobial Surfaces

“…The main problem is the difficulty to synthesize and stabilize the four membered aza-heterocyclic rings in the polymer [25]. To solve this problem we reported easy one pot synthetic approaches to prepare well-defined azetidinium functionalized polymers [26,27]. In the current work, the polymers were prepared via post polymer modification as reported in literature (Scheme 1).…”

Surface treatment of cellulose nanocrystals (CNC): effects on dispersion rheology

“…These modifications are here denoted MorphOMe, diHexylOMe and diAllylOMe, respectively. The grafting was performed using substituted azetidinium salts following a procedure outlined by Chattopadhyay et al (2012). By adding these azetidinium salts to CNC dispersed in a DMSOtoluene mixture, the azetidinium ion reacts with the sulphate groups on the CNC surface.…”

“…The azetidinium salts were prepared following procedures described in the literature (Chattopadhyay et al 2012) with some modifications. The general procedure consisted of dropwise adding one mole equivalent of epichlorohydrin to a solution of one mole equivalent of secondary amine and solvent.…”

“…An example is the report by Chattopadhyay et al (2012) and the salt is most probably together with epichlorohydrin a reactive group in the wet-strength agent polyamideamine-epichlorohydrin (PAE). In the review by Espy (1995) it is stated that alcohol groups may play a part in cross-linking reactions as well as carboxylate end groups of cellulosic polymers.…”

Multifunctional Poly(Vinyl Amine)s Bearing Azetidinium Groups: One Pot Preparation in Water and Antimicrobial Properties

“…[14,15] Recently, we reported a very simple and efficient method to prepare azetidinium functionalized polymers via a coupler approach. [16,17] The advantage of azetidinium functionalized polymers is, that beside ionic interactions covalent bonds with suitable substrates and cross-linking within the polymer film are possible, increasing the stability of the film or coating.…”