Synthesis of poly(isopropenylphenoxy propylene carbonate) and its facile side‐chain functionalization into hydroxy‐polyurethanes

Abstract

4‐Isopropenyl phenol (4‐IPP) is a versatile dual functional intermediate that can be prepared readily from bisphenol‐A (BPA). Through etherification with epichlorohydrin to the phenolic group of 4‐IPP, it can be converted into 4‐isopropenyl phenyl glycidyl ether (IPGE). On further reaction with carbon dioxide in the presence of tetra‐n‐butyl ammonium bromide (TBAB) as the catalyst, IPGE was transformed into 4‐isopropenylphenoxy propylene carbonate (IPPC) in 90% yield. Cationic polymerization of IPPC with strong acid such as trifluoromethanesulfonic acid or boron trifluoride diethyl etherate as the catalyst at −40 °C gave a linear poly(isopropenylphenoxy propylene carbonate), poly(IPPC), with multicyclic carbonate groups substituted uniformly at the side‐chains of the polymer. The cyclic carbonate groups of poly(IPPC) were further reacted with different aliphatic amines and diamines resulting in formation of polymers with hydroxy‐polyurethane on side‐chains. Syntheses, characterizations of poly(IPPC) and its conversion into hydroxy‐polyurethane crosslinked polymers were presented. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016, 54, 802–808

Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO2 Utilization

“…[79] The carbonation of glycidyl methacrylate (GMA) could be carriedo ut quantitatively in the presence of nanolamellar zinc-cobalt double metal cyanide complex (DMCC) as aL ewis acid catalyst (0.3 mol %Z n) with cetyl ammonium bromide (CTAB, 0.65 mol %) as nucleophile affording 2g in ap ure and colorless form, which is suitable for homopolymerization. [82] 2j was used for cationic homopolymerization throught he isoprenyl group, leading to polymers with pendant cyclic carbonates that were cured by reaction with diamines. [81] Synthesis and applicationso fm onomer 2i,a so btained either from GD or from GC, are discussed in al ater section, in combination with the preparation of ab iscarbonate (bis-5CC)a nalogue.…”

“…Reactiono fI PP with ECH produced IPP-glycidyl ether that could be carbonateda t8 0 8Cu nder CO 2 purging. [82] 2j was used for cationic homopolymerization throught he isoprenyl group, leading to polymers with pendant cyclic carbonates that were cured by reaction with diamines. 2k and 2l were synthesized for the preparation of remendable NIPU, exploiting the reversibility of the Diels-Alder reaction.…”

Development in Synthesis and Coating Applications of Polyurethane

“…Polyhydroxyurethane was considered as a suitable substitution for PUs based on isocyanates [44]. One shot mechanism and epoxidation of cyclic carbonate was also reported [45,46].These all are summarized in Table 3.…”

Synthesis and fabrication of highly functionalized Jeffamine antimicrobial polymeric coating

“…They provide flexibility for applications like water‐based coatings, water‐swellable polyamides, and textile treatment. Because of its antimicrobial potency, it can be further used in personal care products . They have been implemented in nanoparticle decoration, thermoresponsive hydrogels, and thermoassociative nanoparticles for drug delivery .…”

“…Because of its antimicrobial potency, it can be further used in personal care products. [16][17][18] They have been implemented in nanoparticle decoration, 19 thermoresponsive hydrogels, and thermoassociative nanoparticles for drug delivery. 20,21 Jeffamine can be used alone or in combination with PEI in the decoration of dendrimers.…”