Novel synthesis of polyphosphonates by the polyaddition of bis(epoxide) with diaryl phosphonates

Minegishi, Shouji; Komatsu, Shinji; Kameyama, Atsushi; Nishikubo, Tadatomi

doi:10.1002/(sici)1099-0518(19990401)37:7<959::aid-pola11>3.0.co;2-7

Cited by 26 publications

(17 citation statements)

References 16 publications

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“…Phosphate-and phosphonate-containing polymers are one of the most important types for phosphorus-containing polymers which have great commercial interest, due to their flame-retardant characteris- tics [195,196] and their potentional use as high-performance plastics [197]. Moreover, a new class of biodegradable polymers belonging to polyphosphate has been reported [198,199].…”

Section: Phosphorus-containing Polymersmentioning

confidence: 99%

Organometallic Ferrocene- and Phosphorus-Containing Polymers: Synthesis and Characterization

Hussein

Asiri

2012

Designed Monomers and Polymers

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The inclusion of organometallic units into polymeric structures has attracted much attention in different fields according to the nature and behaviour of the inserted metal. Moreover, the discovery of organometallic polymers and their structural characterization initiated an explosive rebirth of organometallic chemistry. Organometallic moieties are in or pendent to the polymer backbone and examine some of the uses of the emergent metallocene polymers, and new uses are still being found for these remarkable organometallic moieties. This review gives a simple introduction to variable organometallic molecules and their characteristics. This review will focus on the syntheses and characterization of organometallic polymers, including ferrocene-and phosphorus-containing polymers. A general overview on ferrocene polymers with a special attention to ferrocene-containing liquid crystalline polymers (including a ferrocene moiety in the main chain, side-chain or dendrimers) and fullerene-ferrocene liquid crystalline polymers is presented. In addition, more details for synthesis and properties of phosphorus-containing polymers are illustrated.

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Section: Phosphorus-containing Polymersmentioning

confidence: 99%

Organometallic Ferrocene- and Phosphorus-Containing Polymers: Synthesis and Characterization

Hussein

Asiri

2012

Designed Monomers and Polymers

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“…A singlet peak at 3.58 ppm was assigned to H(a) related to methyl protons and a broad singlet peak at 7.47 ppm was assigned to H(b) (Figure 6). Also, the 13 C NMR spectrum of 6 showed eight different carbon atoms (Figure 7). Furthermore, the 31 P NMR spectrum of the compound 6 shows a peak at 43.70 ppm related to the chemical shift of the phosphine oxide (Figure 8).…”

Section: Synthesis Di(n-carbomethoxylaminomethyl) Benzyl Phosphine Oxmentioning

confidence: 99%

“…Polyphosphonates and polyphosphates are of commercial interest because of their flame-retarding characteristics and their potential as high-performance plastics. [12,13] Although they have some attractive properties, such as good transparency and hardness, the obvious disadvantage is the lack of long-term hydrolytic stability, which limited their usage in many practical applications. This problem has been partially overcome by elimination of the phosphorus-oxygen bonds in the backbone of polymers.…”

Section: Introductionmentioning

confidence: 99%

Phosphorus-containing polymers from THPS.I. Design, synthesis, and characterization of novel monomer and polyureas

Tan

Zhang

Guo³

et al. 2014

Designed Monomers and Polymers

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A new phosphorus-containing dicarbamates, di(N-carbomethoxylaminomethyl)benzyl phosphine oxide was first synthesized from tetrakis(hydroxymethyl)phosphonium sulfate (THPS) via five step reactions (Scheme 1), and its structure was proved by FTIR, ( 1 H, 13 C, and 31 P) NMR, and MS. A series of thermally stable phosphorus-containing polyureas were synthesized via trans-ureation polycondensation of the new monomer with aliphatic diamines, including poly(propylene glycol) bis(2-aminopropyl ether), respectively. All of the above polyureas were fully characterized by inherent viscosity, GPC, solubility tests, and thermogravimetric analysis. The thermal gravimetric analysis results showed that the initial breakdown temperature of all phosphorus-containing polyureas was observed at above 265°C while complete weight loss occurred in the region of 406-465°C, which shows all polyureas have good thermal stability. GPC results showed that the maximum number-average molecular weight of the synthesized polyureas reached 59,100 g mol. The solubility tests results demonstrated that incorporating the ether moieties into the polymer main chain can enhance the solubility of polyureas in organic solvents.

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“…We also examined the reaction of oxetanes with carboxylic acid, and similar results were obtained as mentioned earlier. 22 and phosphonic dichlorides 23 proceed in the presence of quaternary onium salts and crown ether complexes, affording the corresponding polymers. Furthermore, high performance epoxy resins were investigated based on the thermal curing reaction of epoxides with active esters.…”

Section: Kinetics Of the Addition Reaction Of Oxetanes With Protonic mentioning

confidence: 99%

“…[7][8][9] More than 20 years ago, Nishikubo and his coworkers developed new addition reactions of epoxides with certain aprotic reagents. [10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25] On the other hand, oxetane has almost the same strain energy (107 kJ/mol) as epoxide 1 and its basisity of oxygen atom was higher than any other cyclic ethers. It was reported that the cationic polymerization of oxetanes proceed easily to afford the corresponding polyethers in high yields.…”

Section: Introductionmentioning

confidence: 97%

Catalytic reactions of oxetanes with protonic reagents and aprotic reagents leading to novel polymers

Kudo

Nishikubo

2007

J. Polym. Sci. A Polym. Chem.

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This paper reports new addition reactions of oxetanes with certain protonic reagents such as carboxylic acid, phenol, and thiol, and with certain aprotic reagents such as acyl chloride, thioester, phosphonyl dichloride, silyl chloride, and chloroformate using quaternary onium salts as catalysts. The kinetic study of the addition reactions of oxetanes was also investigated. These new addition reactions were applicable to the synthesis of new polymers. These polyaddition systems could also construct both polymer main chains and reactive side chains. The alternating copolymerization of oxetanes with carboxylic anhydride was performed. Furthermore, it was found that anionic ring-opening polymerization of oxetanes containing hydroxy groups proceeded to afford the hyperbranched polymer (HBP) with an oxetanyl group and many hydroxy groups at the ends of the polymer chains. Alkali developable photofunctional HBPs were synthesized by the polyaddition of bis(oxetane)s or tris(oxetane)s, and their patterning properties were examined, too. The photo-induced cationic polymerization of the polymers with pendant oxetanyl groups and the thermal curing reactions of polyfunctional oxetanes (oxetane resins) were also examined to give the crosslinking materials quantitatively.

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Novel synthesis of polyphosphonates by the polyaddition of bis(epoxide) with diaryl phosphonates

Cited by 26 publications

References 16 publications

Organometallic Ferrocene- and Phosphorus-Containing Polymers: Synthesis and Characterization

Organometallic Ferrocene- and Phosphorus-Containing Polymers: Synthesis and Characterization

Phosphorus-containing polymers from THPS.I. Design, synthesis, and characterization of novel monomer and polyureas

Catalytic reactions of oxetanes with protonic reagents and aprotic reagents leading to novel polymers

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