Poly(N-protected ethylene imine-alt-ethylene sulfide) block to functionalize polymeric materials

Hori, Yoichi; Pei, Na; Kumagai, Ryota; Sasanuma, Yuji

doi:10.1039/c1py00264c

Cited by 10 publications

(6 citation statements)

References 19 publications

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“…These modified microspheres were developed for ion exchange purposes. In another example, Sasanuma and co-workers [207] reported on the synthesis of a dithiol monomer for the thiol-ene photopolymerization with a diene monomer forming poly(N-tosyl-ethylene imine-alt-ethylene sulfide). This was done by the chemical modification of diethanolamine as a starting product for both monomers, using thiourea as the source of sulfur.…”

Section: Thiourea and Thiodimethylformamidementioning

confidence: 98%

Protected thiol strategies in macromolecular design

Goethals

Frank

Prez

2017

Progress in Polymer Science

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Section: Thiourea and Thiodimethylformamidementioning

confidence: 98%

Protected thiol strategies in macromolecular design

Goethals

Frank

Prez

2017

Progress in Polymer Science

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“…For pharmaceutical background to sulfonamides, see: Casini et al (2002); Chambers & Jawetz (1998). For an alternative synthesis, see: Hori et al (2011). For a related structure, see: Yoon et al (2001).…”

Section: Related Literaturementioning

confidence: 99%

“…M.P: 95-98 0 C; 1H NMR 500 MHz, CDCl 3 : 7.70 (d, 2H), 7.33 (d, 2H), 3.87 (t, -CH 2 OH, 4H), 3.23 (t, -CH 2 N-, 4H), 2.43 (s, -CH 3 , 3H). The synthesis of (1) has also been reported using triethylamine rather than pyridine (Hori et al, 2011).…”

Section: S2 Experimentalmentioning

confidence: 99%

N,N-Bis(2-hydroxyethyl)-4-methylbenzenesulfonamide

Mushtaq¹,

Khan²,

Yar³

et al. 2012

Acta Crystallogr E Struct Rep Online

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In the title compound C11H17NO4S, an intramolecular O—H⋯O hydrogen bond forms an S(8) ring and determines the conformation of the bis(2-hydroxyethyl) segment of the molecule, holding the two CH2CH2OH groups close to coplanar (r.m.s. deviation = 0.185 Å). In the crystal, O—H⋯O hydrogen bonds link the molecules into zigzag chains along the b axis. Weaker additional C—H⋯O and C—H⋯π contacts generate a three dimensional network, with molecules stacked along the b-axis direction.

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“…[1][2][3][4][5][6][7][8][9] The typical synthetic methods of aliphatic poly(thioether)s include (1) ring-opening polymerization (ROP) of episulfides, 4,[10][11][12] (2) nucleophilic substitution of dihalides with dithiols, 10,13,14 and (3) thiol-ene click polymerization of dithiols and dienes. [15][16][17][18][19][20][21] However, the feasible monomers of these methods are intensely difficult to obtain on a large scale 12,22 and always require special storage owing to their exceedingly high reactivity. 10,23 Therefore, the large-scale application of these methods to synthesize poly(thioether)s is still restricted.…”

Section: Introductionmentioning

confidence: 99%

“…Aliphatic poly(thioether)s are extremely promising in a multitude of applications such as energy storage, heavy metal removal, optical, biological, and self‐assembled materials 1–9 . The typical synthetic methods of aliphatic poly(thioether)s include (1) ring‐opening polymerization (ROP) of episulfides, 4,10–12 (2) nucleophilic substitution of dihalides with dithiols, 10,13,14 and (3) thiol‐ene click polymerization of dithiols and dienes 15–21 . However, the feasible monomers of these methods are intensely difficult to obtain on a large scale 12,22 and always require special storage owing to their exceedingly high reactivity 10,23 .…”

Section: Introductionmentioning

confidence: 99%

One‐pot, one‐step, and selective terpolymerization of ethylene oxide, propylene oxide, and COS to copoly(thioether)s with tunable thermal properties

Kiriratnikom

Zhang

Cao

et al. 2021

Journal of Polymer Science

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Facile construction of sulfur-rich polymers using readily available raw chemicals is an area aggressively pursued but challenging. Herein we use common feedstocks of ethylene oxide (EO), propylene oxide (PO), and carbonyl sulfide (COS) to synthesize copoly(thioether)s which are traditionally produced from unpleasant and difficult to store episulfides. In this protocol, the EO/COS coupling selectively generates a pure poly(ethylene sulfide) (PES) with melting temperature (T m ) values up to 172 C and high yields up to 98%. The EO/PO/COS terpolymerization leads to the incorporation of soft poly(propylene sulfide) (PPS) and hard PES segments together, affording a random PES-co-PPS copoly(thioether) with the complete consumption of EO and PO. Additionally, by simply varying the EO/PO feeding ratio, the obtained copoly(thioether)s possess tunable thermal properties, T m values in the range of 76-144 C, and excellent solubility. These copolymerizations are conducted in one-pot/one-step at industrially favored reaction temperatures of 100-120 C using catalysts of common organic bases, suggesting a facile and practical manner. Especially, the copoly(thioether) exhibits high refractive indices up to 1.68 owing to its high sulfur content, suggesting a broad application prospect in optical materials.

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Poly(N-protected ethylene imine-alt-ethylene sulfide) block to functionalize polymeric materials

Cited by 10 publications

References 19 publications

Protected thiol strategies in macromolecular design

Protected thiol strategies in macromolecular design

N,N-Bis(2-hydroxyethyl)-4-methylbenzenesulfonamide

One‐pot, one‐step, and selective terpolymerization of ethylene oxide, propylene oxide, and COS to copoly(thioether)s with tunable thermal properties

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