Linear polythioesters, XXIII. Products of interfacial polycondensation of 4,4′‐dimercaptobiphenyl with acid dichlorides

Podkościelny, Wawrzyniec; Tarasiuk, Bogdan

doi:10.1002/apmc.1993.052070116

Cited by 12 publications

(4 citation statements)

References 14 publications

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“…The results of the low inherent viscosity experiments, however, indicated that only low molecular weight polymers were isolated. On the other hand, utilizing interfacial polycondensation in the presence of NaOH as HCl scavenger ( Scheme ) yielded polythioesters with high molecular weight values (reduced inherent viscosity, ŋ red , up to 2.5 dL·g −1 ) and high yields (up to ≈99%) . Apart, these polymers exhibited high thermal stability (up to 450 °C), were resistant to diluted alkali or mineral acids, and displayed characteristics of fiber‐forming polymers.…”

Section: Chemistrymentioning

confidence: 99%

Sulfur Chemistry in Polymer and Materials Science

Mutlu

Ceper

et al. 2018

Macromol. Rapid Commun.

254

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.

254

220

View full text Add to dashboard Cite

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“…Koizumi et al synthesized polysulfide by the polyaddition reaction of dithiol and epoxide 3. The syntheses of polythioesters by interfacial polycondensation of aromatic and aromatic dithiols with aromatic and aliphatic acid dichlorides have been reported by Podkoscielny et al4–7 Shaffer et al found that polythioethers and copolythioethers with methylene numbers of 2–10 derived from 4,4′‐biphenyldithiol and α,ω‐dibromoalkanes exhibited thermotropic liquid crystalline characteristics 8. Chen et al reported that incorporation of bis(4,4′‐hydroxyphenyl)sulfide (TDP) improves the flexibility of polyarylate with poor impact strength 9…”

Section: Introductionmentioning

confidence: 98%

Linear polymers with sulfur in the main chain. II. Synthesis of polyesters by interfacial polycondensation of bis(4,4′‐hydroxyphenyl)sulfide with several aliphatic acid dichlorides and their properties

Honda

Watase

Tanaka

2003

J of Applied Polymer Sci

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ABSTRACT:The synthesis and properties of sulfur-containing polyesters derived from bis(4,4Ј-hydroxyphenyl)sulfide (TDP) and various acid dichlorides (AC) have been studied to evaluate the effect of the incorporation of sulfur in the main chains of polyesters. Polyesters derived from TDP and AC (with methylene numbers of 2-10) were synthesized by interfacial polycondensation in a 1,1,2,2-tetrachloroethane /water mixture using tetra-n-butyl ammonium bromide as a phase transfer catalyst. Through the use of gel permeation chromatography, it was determined that the polyesters thus obtained had high molecular weights. The thermal properties of the polyesters including the TDP moiety were evaluated by thermogravimetry/differential thermal analysis and by differential scanning calorimetry. The analyses indicated that the polyesters including the TDP moiety were crystalline polymers with relatively high heat resistance. These polyesters were found to show an odd-even effect with the glass transition temperature and the melting point based on the methylene numbers. The tensile strength and storage modulus decreased with the methylene numbers. It was further found that the polyesters evidenced excellent barrier properties towards oxygen gas having an odd-even effect. In particular, it was shown that the polyesters with methylene numbers of 3, 4, 6, and 8 of methylene units have lower oxygen permeability than poly(ethylene terephthalate) (PET).

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“…Koizumi et al6 synthesized polysulfide by the polyaddition reaction of dithiol and epoxide. The syntheses of polythioesters by interfacial polycondensation of aromatic and aromatic–aliphatic dithiols with aromatic and aliphatic acid dichlorides have been reported by Podkoscielny et al7–12 Shaffer and Percec13 found that polythioethers and copolythioethers with methylene numbers of 2–10 derived from 4,4′‐biphenyldithiol and α,ω‐dibromoalkanes exhibited thermotropic liquid crystalline characteristics. Chen et al14 reported that incorporation of 4,4′‐thiodiphenol (TDP) improves the flexibility of polyarylate with poor impact strength.…”

Section: Introductionmentioning

confidence: 87%

Linear polymers with sulfur in the main chain III. Synthesis of polythioesters by polycondensation of bis(4,4′‐mercaptophenyl)sulfide with various acid dichlorides and their properties

Honda

Watase

Tanaka

2005

J of Applied Polymer Sci

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Synthesis and properties of sulfur-containing linear polythioesters derived from bis(4,4Ј-mercaptophenyl)-sulfide (MPS) and various acid dichlorides (AC) have been studied to evaluate the effect of the thioester group in comparison with corresponding linear polyesters. Polycondensations between MPS and azelaoyl chloride (AZC) chosen as a model reaction system were investigated under various conditions by solution polycondensation, to find optimal conditions to get high molecular weight and quantitative yield. The obtained polymer using chloroform as a solvent indicated the highest molecular weight, determined by gel permeation chromatography (GPC). Thus the polythioesters from MPS and AC were synthesized under the above-mentioned conditions. The thermal properties of polythioesters including the MPS moiety were evaluated by thermogravimetry/differential thermal analysis (TG/DTA), and differential scanning calorimetry (DSC). Those indicated that the polythioesters including the MPS moiety were crystalline polymers with relatively high heat resistance. These polythioesters were found to show an odd-even effect with the glass transition temperature, melting point, and oxygen permeability based on the methylene numbers. The tensile strength and storage modulus decreased with the number of methylene units.

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Linear polythioesters, XXIII. Products of interfacial polycondensation of 4,4′‐dimercaptobiphenyl with acid dichlorides

Cited by 12 publications

References 14 publications

Sulfur Chemistry in Polymer and Materials Science

Sulfur Chemistry in Polymer and Materials Science

Linear polymers with sulfur in the main chain. II. Synthesis of polyesters by interfacial polycondensation of bis(4,4′‐hydroxyphenyl)sulfide with several aliphatic acid dichlorides and their properties

Linear polymers with sulfur in the main chain III. Synthesis of polythioesters by polycondensation of bis(4,4′‐mercaptophenyl)sulfide with various acid dichlorides and their properties

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