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Nishikubo, Tadatomi; Kameyama, Atsushi

doi:10.1295/kobunshi.42.932c

Cited by 6 publications

(6 citation statements)

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“…These rethat trace amounts of water contained in the hydrophilic solvents, which could not be removed sults show that TBAB and TBPB exhibit high catalytic activity towards polycondensation of BPAF completely, caused the hydrolysis of dichlorocontaining compound BCMO. 25 In addition, the with BCMO.…”

Section: Resultsmentioning

confidence: 99%

Preparation of new polyether with oxetane pendant group

Liaw¹,

Liang²,

Liaw³

1998

J. Polym. Sci. A Polym. Chem.

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A new oxetane‐containing polyether was synthesized by polycondensation of bisphenol‐AF (BPAF) with 3,3‐bis(chloromethyl)oxetane (BCMO) using the phase‐transfer catalyzed method. The polycondensation proceeded very smoothly in aromatic solvents, catalyzed by quaternary ammonium or phosphonium salts, such as tetrabutylammonium bromide (TBAB) and tetrabutylphosphonium bromide (TBPB), to afford the polymer with high yield and molecular weight. Further, a polymer with relatively high molecular weight was obtained when the reactions were carried out in aromatic and lipophilic solvents such as benzene and nitrobenzene. The modification of this oxetane‐containing polyether was easily achieved by carrying out ring‐opening of the oxetane ring by using hydrogen chloride in methylene chloride, which produced a functional polymer containing hydroxyl and chloro groups. The oxetane‐containing polyether was observed to be soluble in chlorinated aliphatic hydrocarbons such as methylene chloride and chloroform, as well as polar solvents such as DMSO, DMF, and DMAc, and also some common organic solvents such as benzene and toluene. However, it was insoluble in both aliphatic hydrocarbons as well as alcoholic solvents. The oxetane‐containing polyether was observed to start losing weight at around 300°C under nitrogen atmosphere, and 10% weight loss was measured to be 411°C. The glass transition temperature of the oxetane‐containing polyether was measured to be 134°C and the wide‐angle X‐ray diffraction pattern revealed this polymer to be semicrystalline. © 1998 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 36: 103–107, 1998

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Section: Resultsmentioning

confidence: 99%

Preparation of new polyether with oxetane pendant group

Liaw¹,

Liang²,

Liaw³

1998

J. Polym. Sci. A Polym. Chem.

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“…A facilerouteto convert polyisoprene into a bio-compatible heparin analogueis by usingN-chlorosulfonyl isocyanate [232]. In many PAR, the precursor block copolymer is transformed into a functional intermediate; such as epoxidation reaction of the double bonds in polybutadiene segment, that subsequently be transformed into functional block copolymer through a wide range of reactions [235][236][237][238]. In many PAR, the precursor block copolymer is transformed into a functional intermediate; such as epoxidation reaction of the double bonds in polybutadiene segment, that subsequently be transformed into functional block copolymer through a wide range of reactions [235][236][237][238].…”

Section: Polymer-analogue Reaction (Par)mentioning

confidence: 99%

Functional Nanostructures

2008

Nanostructure Science and Technology

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“…This may be due to good mutual solubility between cal- ixarene 18d and DPSP, or to higher concentration of the spiro ortho ester groups in the same cubic measures of the calixarene derivatives. 41 The reaction behavior of thermal curing of epoxy resins with calixarenes using certain catalysts was examined in bulk. The conversions of the reaction could be monitored by decrease of the characteristic peak of oxirane groups at 910 cm −1 in FT-IR spectrum.…”

Section: Photoinitiated Cationic Polymerization Of Calixarenes Contaimentioning

confidence: 99%

Novel High Performance Materials. Calixarene Derivatives Containing Protective Groups and Polymerizable Groups for Photolithography, and Calixarene Derivatives Containing Active Ester Groups for Thermal Curing of Epoxy Resins

Nishikubo

Kameyama

Kudo

2003

Polym J

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ABSTRACT:This paper reviews our recent studies on the syntheses and functions of novel calixarene derivatives with excellent thermal stability as high performance materials. Calixarene derivatives containing protective groups such as tert-butoxycarbonyl (t-Boc), trimethylsilyl (TMS), and cyclohexenyl (CHE) groups were successfully prepared by the reaction of certain calixarenes, p-methylcalix [6]arene (1a), p-tert-butylcalix [8]arene (1c), and Cmethylcalix [4]resorcinarene (1d) with the corresponding protecting reagents. Calixarene containing radically polymerizable groups such as methacryloyl groups and cationic polymerizable groups such as propargyl, vinyl ether groups were prepared in good yields. Calixarene derivatives containing cyclic ethers such as oxirane, oxetane, and spiro orthoesters were also prepared. Calixarene derivatives thus obtained had good film forming property and thermal stability. It was proved that the photoinduced deprotection of the calixarene derivatives containing protective groups in the presence of a photo-acid generator proceeded easily to give the corresponding calixarenes with phenol groups. Photoinitiated polymerization of the calixarenes with various polymerizable groups using suitable photoinitiators in the film state proceeded efficiently to produce crosslinked films. Furthermore, thermal curing of epoxy resins with calixarenes (1a, 1c, 1d), and calixarenes containing active ester groups using certain catalysts were studied to found that the calixarenes were useful curing agents for epoxy resins.KEY WORDS Calixarene / Thermal Stability / Protective Group / Polymerizable Group / Photoinduced Deprotection / Radical Polymerization / Cationic Polymerization / Thermal Curing / Epoxy Resin / Calixarenes are cyclic oligomers prepared 1 ordinarily from the reaction of phenols with aldehydes, and have attracted much interest in the field of host-guest chemistry. 2 Therefore, over the last 20 years, synthesis 3 of various calixarene derivatives and chemical modification 4, 5 of calixarenes have been studied in attempting to induce the targeted character. We can consider that calixarene derivatives have further advantage in synthetic organic chemistry as starting materials due to polyfunctional hydroxyl groups, which are readily modified to various functional groups. That is, in polymer synthesis, calixarene derivatives can also be used as multifunctional initiators for the synthesis of starshaped polymers. Kennedy and his co-workers 6 reported the synthesis of a star-shaped polymer with eight arms of poly(iso-butylene) using calix [8]arene derivative as an initiator. Sawamoto and his co-workers 7 succeeded in producing certain star-shaped polymer with 4-8 arms of poly(methyl methacrylate) using cal- † To whom correspondence should be addressed. ixarene derivative as initiator.Recently, it was also suggested that calixarenes have unique characteristics such as small molecular size, good film-forming properties, 8, 9 high glass transition temperature 10 (T g ), excellent thermal stabilit...

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Cited by 6 publications

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Preparation of new polyether with oxetane pendant group

Preparation of new polyether with oxetane pendant group

Functional Nanostructures

Novel High Performance Materials. Calixarene Derivatives Containing Protective Groups and Polymerizable Groups for Photolithography, and Calixarene Derivatives Containing Active Ester Groups for Thermal Curing of Epoxy Resins

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