Studies on reactions of the <i>N</i>‐phosphonium salts of pyridines. XIII. Direct polycondensation reaction of carbon dioxide or disulfide with diamines under mild conditions

Yamazaki, Noboru; Iguchi, Tadao; Higashi, Fukuji

doi:10.1002/pol.1975.170130402

Cited by 32 publications

(27 citation statements)

References 5 publications

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“…Nevertheless, literature survey depicts that polymers having thiourea functional groups in the main chain can be readily synthesized by the following reactions of a diamine with: A) CS 2 ; B) thiourea; C) thiophosgene; D) diisothiocyanate; E) 1,1′‐thiocarbonyldiimidazole; and F) elemental sulfur and diisocyanides ( Scheme A–F), respectively.…”

Section: Chemistrymentioning

confidence: 99%

Sulfur Chemistry in Polymer and Materials Science

Mutlu

Ceper

et al. 2018

Macromol. Rapid Commun.

258

220

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The ORCID identification number(s) for the author(s) of this article can be found under https://doi.org/10.1002/marc.201800650. ChemistryBefore moving to the recent advances within the last 5 years in the diverse applications of sulfur chemistry in polymer and Sulfur-Containing PolymersSulfur and its functional groups are major players in an area of exciting research taking place in modern polymer and materials science, both in academia and industry. In fact, manifold sulfur-based reactions that are both exceptionally versatile as well as tremendously useful have been implemented, and further utilized for the design and preparation of polymeric materials that lead to a plethora of applications ranging from medicine to optics and nanotechnology to separation science. Hence, within this review, an overview of strategies and developments used over the last 5 years to reinforce the importance of the sulfur functional group in modern polymer and materials science is presented. In particular, many important references in the primary literature of sulfur chemistry are referred to, including thiol-ene, thiol-yne, thiol-Michael addition, disulfide cross-linking, and thiol-disulfide exchange, among others, by explaining and illustrating the important principles. Last but not least, the grand aim to underpin the importance of sulfur in modern polymer and materials science is achieved by presenting selected examples in diverse fields and postulating the respective potential for real-world applications. he is now a full professor at KIT.sulfur atoms, and tetraphenylethene-bearing di(alkyl bromide) (Scheme 3). The yield of the polymerization was dependent on the di(alkyl bromide) monomer; the longer spacer between the aromatic moiety and the reactive bromide end groups Scheme 1. The discussion henceforth focuses on the synthesis of polymers possessing the depicted sulfur functional groups. Scheme 2.Representative examples of polythioethers prepared via A) the nucleophilic substitution reaction between an electrophilic dihalide with nucleophilic derivatives of dithiols under alkaline conditions; B) the thiol-ene/yne addition reaction between AA and BB type monomers (i.e., dithiols and dienes/diynes); and C) radical or ionic ring-opening of sulfurcontaining strained rings.Scheme 3. The thiol-bromo polymerization of conformationally fixed monomers to provide multifunctional polymers. [19] Macromol. Rapid Commun. 2019, 40, 1800650 Scheme 4. The regioselective selective nucleophilic aromatic substitution between thiol and fluorinated aromatic compounds, the para-fluorothiol reaction (PFTR).Scheme 5. Synthesis of a linear polymer via PFTR-reaction. [21]

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Section: Chemistrymentioning

confidence: 99%

Sulfur Chemistry in Polymer and Materials Science

Mutlu

Ceper

et al. 2018

Macromol. Rapid Commun.

258

220

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“…19 Moreover, it is possible to produce the feedstock of dimethyl carbonate and propylene carbonate from carbon dioxide with methanol and propylene glycol. [25][26][27] Our previous investigation demonstrated that urea derivates could be easily produced from alkyl amines and carbon dioxide under reaction conditions similar to those for the analogous urea. Recently, the chemical xation and utilization of carbon dioxide has attracted much attention in the elds of environmental protection, new energy resources and advanced materials.…”

Section: Introductionmentioning

confidence: 96%

Utilization of carbon dioxide to build a basic block for polymeric materials: an isocyanate-free route to synthesize a soluble oligourea

Zhao

Zhang

et al. 2015

RSC Adv.

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A water soluble oligourea was synthesized by an isocyanate-free route from carbon dioxide and diamine in the absence of any organic solvents or additives. The chemical structure of the product was confirmed by FTIR and 13 C NMR analysis, and the average molecular weight was estimated with MALDI-TOF MS. The weight average molecular weight of the obtained oligourea is about 2210 Da reacting under 180 C and 11 MPa for 12 h. Moreover, the prepared oligourea has a moderate thermo-stability, it has an initial decomposition temperature at $220 C and a melting temperature of 110 C, as confirmed by TGA and DSC. As a soluble oligomer, it could be used as a building block to synthesize CO 2 -based polymeric materials due to it possessing a chemically active amino end group. For example, foaming plastics, greases, spun fibers and high strength polymer materials may be fabricated by reaction of the oligomer with a chain extender like a diisocyanate, diester or diacid.

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“…'H NMR chemical shifts,6, and electronegativities, X A I , of AIEt3/Lewis base Lewis base/A1Et3= 1: 1, by mole; [AlEt3]= 1,0 M in toluene; temp. 4.…”

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confidence: 99%

Copolymerization of carbon dioxide and some oxiranes by organoaluminium catalysts

Koinuma

Hirai

1977

Makromol. Chem.

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Carbon dioxide was copolymerized with methyloxirane and 7‐oxabicyclo[4.1.0]heptane using triethylaluminium as a catalyst component. Factors to control the copolymer composition were sought on the basis of an assumed copolymerization mechanism. Compared to nonpolar solvents, ethereal solvents were found to increase the carbon dioxide content in the copolymer obtained by the triethylaluminium/water system, giving a fraction with almost alternating sequence. The addition of a Lewis base, especially treiphenylphosphine, to triethylaluminium was also useful to get copolymers of high carbon dioxide content. The coincidence of these results with the expectation from the assumed copolymerization scheme clearly indicates that the copolymerization proceeds through a coordinated anionic mechanism.

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Studies on reactions of the N‐phosphonium salts of pyridines. XIII. Direct polycondensation reaction of carbon dioxide or disulfide with diamines under mild conditions

Cited by 32 publications

References 5 publications

Sulfur Chemistry in Polymer and Materials Science

Sulfur Chemistry in Polymer and Materials Science

Utilization of carbon dioxide to build a basic block for polymeric materials: an isocyanate-free route to synthesize a soluble oligourea

Copolymerization of carbon dioxide and some oxiranes by organoaluminium catalysts

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