Oxa-Michael polyaddition of vinylsulfonylethanol for aliphatic polyethersulfones

Abstract

Polyethersulfones are an interesting class of polymers for industrial applications due to their unusual properties such as a high refractive index, flame-retardant properties, high temperature and chemical resistance. The common...

Phosphine-Catalyzed Vinylation at Low Acetylene Pressure

“…Initially, two mechanisms were considered to be plausible pathways for the observed reactivity, which are similar to the two pathways suggested by Ziegenbalg et al: (1) a base-induced mechanism that would resemble a classical Reppe process and (2) a nucleophilic mechanism inspired by the work of Trost et al . Experiments with N-containing bases did not show any conversion (Table , entries 13–15) at low acetylene pressures; thus, the investigations mainly focused on the nucleophilic mechanism, which remained the energetically favored pathway throughout the whole investigation.…”

Water as a monomer: synthesis of an aliphatic polyethersulfone from divinyl sulfone and water

“…In comparison, Brendel and coworkers reported number average molar masses between 2.2 and 3.7 kg mol −1 ( Đ = 1.3–1.6) for the same polymer prepared from 2-hydroxyethyl vinyl sulfone (measured in LiCl/ N , N -dimethylacetamide based on conventional calibration using poly(ethylene oxide) standards). 19 Increasing the catalyst loading of DMAP to 10 mol%, led to a slight reduction in molar mass averages ( Table 2 , entry 2). Likewise, a reduction of the catalyst loading to 2 mol% DMAP gave even lower molar mass averages, which is in line with a lower double bond conversion in this case.…”

“…Detailed characterization of PES obtained from entry 1 in Table 2 by NMR spectroscopy and matrix-assisted laser desorption ionization time of flight mass spectrometry (MALDI-TOF MS) revealed very similar results as reported for PES obtained from 2-hydroxyethyl vinyl sulfone. 19 In 1 H-NMR spectroscopy, the oxa-Michael repeating unit gives rise to two triplets at 3.81 ppm and 3.42 ppm. As end groups 4-dimethylamino pyridinium (8.28, 7.04 ppm), alcohol units (3.78, 3.26 ppm) and vinyl groups (7.00–6.94, 6.25–6.19 ppm) were observed (Fig.…”

“…The desired aliphatic polyethersulfone (PES) resulting from the potential polyaddition of water and DVS 18 has recently been reported by Brendel and coworkers. 19 They used a different but similar synthetic route performing the oxa-Michael polyaddition of 2-hydroxyethyl vinyl sulfone, priorly prepared by the oxidation of vinylmercaptoethanol. Herein, we present the use of water as a monomer in the oxa-Michael polyaddition with DVS.…”

Does the oxa-Michael reaction of 2-trifluoromethacrylic acid lead to fluorinated polyesters?

“…This study might be developped in copolymerisation processes with diols, vinylsulfones or sulfonate derivatives. 9,52,53…”