Synthesis of Aromatic Polythioethers Containing 1,3,5-Triazine Ring by Aromatic Nucleophilic Substitution Polymerization

Kondo, Shuji; Mori, Hideki; Kadomatsu, Misako; Sato, Koji; Ando, Tsugumichi; Kakuno, Tomohiko; Kunisada, Hideo; Yuki, Yasuo

doi:10.1080/10601329608010897

Cited by 7 publications

(2 citation statements)

References 15 publications

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“…However, it is possible to avoid these side reactions and to prepare poly(thioethers) by using 4,49-thiobisbenzenethiol and a variety of activated dihalides containing different functional groups. The preparation of a variety of amorphous poly(thioether) ketones and triazine containing poly(thioethers) have been reported by using a similar approach 6,7) . .…”

Section: Introductionmentioning

confidence: 98%

Preparation and properties of novel aromatic poly(thioethers) derived from 4,4′-thiobisbenzenethiol

Allam

Liu

McGrath

et al. 1999

Macromol. Chem. Phys.

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SUMMARY: A series of amorphous and semicrystalline aromatic poly(thioethers) have been prepared by the reactions of 4,49-thiobisbenzenethiol and activated dihalides. Azo group activated dihalide monomer was prepared by the reactions of 4-fluoronitrosobenzene with a suitable diamine. The keto and phosphine sulfide containing monomers were synthesized by Friedel-Crafts acylation reactions of suitable halobenzenes with appropriate acid chlorides. Potassium carbonate mediated reactions in dimethylacetamide afforded moderate to high molecular weight polymers. Polymers with high melting points were prepared by using diphenyl sulfone as a co-solvent. The poly(thioethers) exhibit high glass transition temperatures and/or high melting points. In addition, the polymers exhibit excellent thermal stability.

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Section: Introductionmentioning

confidence: 98%

Preparation and properties of novel aromatic poly(thioethers) derived from 4,4′-thiobisbenzenethiol

Allam

Liu

McGrath

et al. 1999

Macromol. Chem. Phys.

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“…7 When a monofunctional compound is introduced into cyanuric chloride, the resulting compounds can be used as difunctional triazine-based monomers for the preparation of polyguanamines, 8,9 polyethers, 10 and polythioethers. 11 The interest in polymers that incorporate the amino-s-triazine moiety is the existence of the strong interaction between polymer main chains via hydrogen bonding, 12 numerous reactive sites along with the polymer backbone to modify the polymer, or the application to photopolymers. Therefore, 2-amino-4,6-dichloro-1,3,5-triazine (ADCT), the monomer of the amino-s-triazine functional polymer has been extensively studied.…”

mentioning

confidence: 99%

Chemoselective Polycondensation of 2-Amino-4,6-dichloro-1,3,5-triazine with Aromatic Diamines

Shibasaki¹,

Koizumi²,

Nishimura

et al. 2011

Chemistry Letters

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Chemoselective polycondensation of 2-amino-4,6-dichloro-1,3,5-triazine (ADCT) was investigated with various aromatic diamines such as 4,4′-oxydianiline (ODA), 9,9-bis(4-aminophenyl)fluorene (BAFL), 4,4′-(hexafluoropropane-2,2-diyl)dianiline (BisAF), and bis(4-aminophenyl)sulfone (SODA) in the presence of potassium carbonate as a base. High-molecular weight perfectly linear polyguanamines (Mn ≈ 46000) were successfully obtained for the polycondensation of ADCT with BisAF, while the polycondensation of ADCT with BAFL afforded branched polyguanamines with a degree of branching of from 0.02 to 0.17.

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Sulfur‐Containing Polymers

Kultys¹

2005

Kirk-Othmer Encyclopedia of Chemical Technology

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This review describes methods of synthesis and some more interesting properties of the various new sulfur‐containing polymers, with particular regard for their potential application possibilities. Also, some new or improved methods of synthesizing already known polymers are discussed. Polysulfides, including poly(monosulfide)s and poly(disulfide)s are the subject of many detailed studies. In the last decade, extensive efforts have been devoted to the synthesis of cyclic oligomers (macrocyclic aromatic sulfides and disulfides) as precursors for the preparation of high molecular weight poly(thioarylene)s by ring‐opening polymerization. The coordination chemistry of macrocyclic polysulfides has also received considerable attention. The thiacrown ether polymer ligands can be used as ion‐exchange resins, metal ion adsorbents, and polymeric phase‐transfer catalysts. Molecular systems in which tetrathiafulvalene is incorporated into macrocycles with supplementary donor atoms are potential electroactive cation sensors. Perfluoro‐ and polyfluorothiophenes have been studied as precursors to novel electrically conductive polymers. Polysulfoxides are used as functional polymers. Polymers with sulfoxide group in the main chain can be used as novel polymeric oxidizing reagents, compatibilizers, and polymer solvents, and those with chiral sulfonyl groups as stationary phases of chiral hplc column or as polymeric reagents. Polysulfonium salts can be used as ion‐exchange resins, polymer supports in peptide synthesis, polymeric reagents, or conducting and photochemical polymeric materials. There have been reports of examples of polymers with sulfonium salt moieties applied as a catalyst to organic reactions and precursors of such polymers as PPS, perfluorinated PPS, PPV, and PPSA. Poly(thiophenium salt)s were found to act as a new type of polymeric alkylation reagents. Polymers substituted by sulfo groups have a wide range of applications. Water‐soluble polymers are used as emulsifiers, flocculants, thickeners, tanning agents, conductive polymers, etc. Sulfonated polyelectrolyte block copolymers are effective stabilizers in emulsion polymerization. Insoluble polymers are used as ion‐exchange resins and they find application as membrane materials. A great demand for chemically stable ion‐exchange membranes for electromembrane processes (such as electrodialysis, polymer electrolyte membrane electrolysis, and polymer electrolyte fuel cells) has, in the past years, stimulated investigations dealing with the developing of the sulfonation process of thermally and chemically stable engineering plastics. Sulfopolymers are employed in biomedical systems. Much effort has been expended to improve blood‐contacting biomaterials, eg, segmented polyurethanes, and develop various polysulfates and polysulfonates as antithrombotic or antiviral agents. Polysulfates also have potential biomedical applications, eg, as antithrombotic agents. Polysulfates in general, and sulfated polysaccharides in particular, are active against a wide variety of enveloped viruses. A major commercial sulfated polysaccharide is carrageenan, used in ice cream and other food products. Polythioesters, polythiocarbonates, as well as polythiourethanes are interesting thermoplastics. Thus, biphenyl‐based polythioesters are high thermal stability polymers. Polythiocarbonates showing a high refractive index are potentially interesting for optical applications. Polymers bearing five‐membered cyclic dithiocarbonate groups in the side chain are potentially the most versatile reactive polymers. Thiopolyurethanes bearing the thiol groups may be used as reactive polymers to produce optical materials. Segmented thiopolyurethanes based on simple thiodiols as chain extenders with poly(tetramethylene oxide) soft segment are high elasticity thermoplastic elastomers. Polymers containing diphenylmethane units with active methylene groups are new, potentially peroxide‐curable, HDI‐based thiopolyurethanes, whereas polymers containing benzophenone units may find use as interesting modifiers of photosensitive polyurethanes. Studies on polysulfoximines, the new potentially high performance engineering plastics, have recently been undertaken.

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Synthesis of Aromatic Polythioethers Containing 1,3,5-Triazine Ring by Aromatic Nucleophilic Substitution Polymerization

Cited by 7 publications

References 15 publications

Preparation and properties of novel aromatic poly(thioethers) derived from 4,4′-thiobisbenzenethiol

Preparation and properties of novel aromatic poly(thioethers) derived from 4,4′-thiobisbenzenethiol

Chemoselective Polycondensation of 2-Amino-4,6-dichloro-1,3,5-triazine with Aromatic Diamines

Sulfur‐Containing Polymers

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