Synthesis of hyperbranched aliphatic polyethers via cationic ring-opening polymerization of 3-ethyl-3-(hydroxymethyl)oxetane

Magnusson, Heléne; Malmström, Eva; Hult, Anders

doi:10.1002/(sici)1521-3927(19990801)20:8<453::aid-marc453>3.0.co;2-b

Cited by 154 publications

(108 citation statements)

References 11 publications

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“…The HBP was derived from the ring-opening polymerization of 3-ethyl-3-(hydroxymethyl)oxetane 36 and was terminated with ethylene oxide to increase flexibility and reduce the viscosity. Table I gives an overview of the physical properties of the acrylated HBP.…”

Section: Methodsmentioning

confidence: 99%

Conversion and shrinkage analysis of acrylated hyperbranched polymer nanocomposites

Geiser

Leterrier

2009

J of Applied Polymer Sci

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The photo-curing behavior of composites containing nanosized SiO 2 in an acrylated hyperbranched polymer matrix was investigated by means of photo differential scanning calorimetry. The chemical conversion data were analyzed using an autocatalytic model, paying close attention to the influence of composition and UV intensity. It was shown that the reaction order and the autocatalytic exponent were independent of UV intensity and filler fraction, whereas the rate constant showed strong intensity dependence, but weak filler dependence. Maximum conversion was independent of UV intensity, but was reduced when a filler was present. The dispersion state influenced the gel-point of the composites, but had no influence on the overall cure kinetics. Cure shrinkage reduction of $ 33% could be achieved by adding 20 vol% of filler. This was attributed to the reduced double bond conversion of the matrix due to the presence of the filler. V

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Section: Methodsmentioning

confidence: 99%

Conversion and shrinkage analysis of acrylated hyperbranched polymer nanocomposites

Geiser

Leterrier

2009

J of Applied Polymer Sci

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“…In addition, Hult and coworkers 9) carried out the cationic polymerization of the same monomer. The monomer used by Penczek et al 8) and Hult et al 9) is similar to the one that we are working on, however, in this work the dependence of the crystallinity of resulting polymers on the catalyst to monomer ratio, which deserves independent publication, was discovered.…”

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confidence: 94%

A new approach to control crystallinity of resulting polymers: Self-condensing ring opening polymerization

Yan¹,

Hou

Zhu

et al. 2000

Macromol. Rapid Commun.

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“…2,3 Hyperbranched polymers by cationic ring-opening polymerization of EHO using sulfonium salts as cationic initiators have been reported. [4][5][6][7] Inoue et al performed living anionic polymerization of oxetanes using aluminum porphyrin/Lewis acid as catalyst. 8 The authors have developed useful reactions of oxetanes for synthetic organic chemistry and polymer synthesis.…”

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confidence: 51%

Synthesis of a Hetero Telechelic Hyperbranched Polyether. Anionic Ring-Opening Polymerization of 3-Ethyl-3-(hydroxymethyl)oxetane Using Potassium tert-Butoxide as an Initiator

Kudo

Morita

Nishikubo

2003

Polym J

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KEY WORDSHetero Telechelic Hyperbranched / Anionic Polymerization / Polyethers / 3-Ethyl-3-(hydroxymethyl)oxetane / Oxetanes with 4-membered ring are polymerized exclusively with cationic initiators, due to high basicity. 1 Vandenberg et al. reported that cationic ring-opening polymerization of 3-ethyl-3-(hydroxymethyl)-oxetane (EHO) in the presence of aluminum complexes as cationic initiators produced linear polymers with high crystallinity and no glass transition temperature. 2, 3 Hyperbranched polymers by cationic ring-opening polymerization of EHO using sulfonium salts as cationic initiators have been reported. [4][5][6][7] Inoue et al. performed living anionic polymerization of oxetanes using aluminum porphyrin/Lewis acid as catalyst. 8 The authors have developed useful reactions of oxetanes for synthetic organic chemistry and polymer synthesis. 9 No research has been done on the anionic polymerization of oxetanes using common anionic initiators such as butyllithium (BuLi), sodium methoxide (MeONa), potassium tert-butoxide (t-BuOK) and etc.Herein, we describe successful results of the anionic ring-opening polymerization of oxetane, 3-ethyl-(3-hydroxymethyl)oxetane (EHO), affording hetero telechelic hyperbranched polyethers, poly(EHO)s containing an oxetanyl and many hydroxyl groups at the ends. EXPERIMENTAL Materials18-Crown-6-ether (18-C-6) was recrystallized twice from acetnitrile. t-BuOK was purified by the sublimation. 3-Ethyl-3-(hydroxymethyl)-oxetane (EHO) was donated from Toagosei Co., Ltd. and distilled over MgSO 4 before use. InstrumentationInfrared (IR) absorption spectra were measured on a Jasco model IR-420 spectrometer. 1 H and 13 C NMR spectra were recorded on a JEOL model JNM α-500 (500 MHz for 1 H NMR and 125 MHz for 13 C NMR) in DMSO-d 6 with Me 4 Si (TMS) as internal standard. The degree of branching was calculated from relative intensity of the -CH 2 CH 3 in proton decoupled, quantitative 13 C NMR spectra. Number-average molecular weight (M n ) and weight-average molecular weight (M w ) of the polymers were estimated by gel permeation chromatography (GPC; TOSOH model HLC-8020) on TSK gel Multipore Hxl-M columns calibrated by narrow molecular weight polystyrene standards and with solution of LiBr and phosphoric acid (20 mM) in dimethylformamide (DMF) as eluent without correction with a refractive index detector. T g s were measured on a Seiko Electronic Instrument (SSC5200/DSC120) differential scanning calorimeter (DSC) at a heating rate of 10 • C min −1 under a nitrogen atmosphere. Thermal analysis was performed on a Seiko Electronic Instrument (TG/DTA 120) at a heating rate of 10 • C min −1 for thermogravimetric analysis (TGA) under nitrogen. Matrixassisted laser desorption ionization time-of flight mass (MALDI-TOF-MS) experiments were performed SHI-MAZU/KRATOS MALDI-TOF-MS using dihydroxy benzoic acid as matrix and chloroform as solvent. Synthesis of Hyperbranched Polyethers by the Polymerization of 3-Ethyl-(3-hydroxymethyl)oxetane (EHO).A typical procedure for the polymerization of E...

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Synthesis of hyperbranched aliphatic polyethers via cationic ring-opening polymerization of 3-ethyl-3-(hydroxymethyl)oxetane

Cited by 154 publications

References 11 publications

Conversion and shrinkage analysis of acrylated hyperbranched polymer nanocomposites

Conversion and shrinkage analysis of acrylated hyperbranched polymer nanocomposites

A new approach to control crystallinity of resulting polymers: Self-condensing ring opening polymerization

Synthesis of a Hetero Telechelic Hyperbranched Polyether. Anionic Ring-Opening Polymerization of 3-Ethyl-3-(hydroxymethyl)oxetane Using Potassium tert-Butoxide as an Initiator

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