Synthesis and polymerization of styrene monomer carrying isothiocyanate moiety and its copolymerization with HEMA based on chemo-selectivity to nucleophiles

Abstract

Isothiocyanate is a very useful functional group for post-polymerization modification by the reaction with amine or alcohol. An isothiocyanate monomer, 4-vinylbenzyl isothiocyanate, was synthesized from 4-vinylbenzyl chloride without using any harmful reagents such as thiophosgene and CS 2 . The obtained monomer was successively polymerized by the conventional radical polymerization (AIBN, 1,4-dioxane, 60 C) to afford the corresponding polymer. The obtained polymer was characterized by 1 H NMR, FTIR, thermogravimetric analysis (TGA), and differential scanning calorimetry. In contrast to the isocyanate group, the isothiocyanate group was relatively tolerant to alcohols, and this character enabled us to synthesize a copolymer of 4-vinyl benzylisothiocyanate and (2-hydroxyethyl methacrylate). The copolymer is transformed into networked polymer by 1,8-diazabicyclo[5.4.0]undec-7-ene as a promoter of the reaction between isothiocyanate and alcohol to afford thiocarbamate. The formation of networked polymer was characterized by FTIR and TGA. V C 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2013, 51, 5215-5220

Reversible Cycling of Graphite Electrodes in Propylene Carbonate Electrolytes Enabled by Ethyl Isothiocyanate

“…31 Meanwhile, although the carbon radical can also exist in this scenario, we exclude radical-based polymerization because −NCS seems to be relatively stable against radical attack. 33 To fully understand the chemical composition of the EITCderived SEI, the graphite electrode charged in a 5% EITC−PC electrolyte is analyzed by XPS and the results are shown in Figure 6. Pristine graphite and a graphite electrode charged in the STD-PC electrolyte are also presented for comparison.…”

Crosslinking and ozone degradation of thermosetting resins based on maleic anhydride/diene copolymer and polyfunctional alcohols

“…The quantitative ring‐opening reaction of the anhydride groups required the harder reaction conditions, such as reflux in toluene for 5 h. The peak due to the anhydride moiety was not observed in the spectrum of the isolated product [Figure (c)]. In the literature, the reactivity of functional groups, such as anhydride, acyl chloride, and isocyanate groups, was reduced when they were incorporated as a part of the polymer repeating structure …”

“…In the literature, the reactivity of functional groups, such as anhydride, acyl chloride, and isocyanate groups, was reduced when they were incorporated as a part of the polymer repeating structure. [25][26][27][28][29][30]…”

Synthesis and decrosslinking of networked polymers having zwitterion structure consisted by cyclic amidine and isothiocyanate

“…The synthesized polymers form strongly crosslinked structure through the parallel ionic interaction among zwitterions and improvement on thermal stability and solvent resistivity resulted. The cyclic amidines that the authors used to form zwitterions are known to function as the catalyst in the synthesis of thiourea and/or thiocarbamate via the reaction of isothiocyanate with amines or alcohols, and the zwitterion compounds that are synthesized from the cyclic amidines and isothiocyanete described above can be considered as the intermediate compounds in the reaction of isothiocyanate where cyclic amidines are used as catalyst. Thus, the authors consider that the changes in the side chain to thioureas and/or thiocarbamates are made possible to the polymers that have zwitterions consisted of cyclic amidines and isothiocyanates.…”