An alternative pathway for the hydrolysis of epoxy ester compounds

Shaw, Sarah; Russo, Tiziana; Qiao, Greg G.

doi:10.1016/j.polymer.2006.10.004

Cited by 26 publications

(17 citation statements)

References 20 publications

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“…The final synthesis step was an exhaustive acidic hydrolysis of non‐reacted oxirane groups on the Si‐pGMA‐TrisA particles, which was done under acetic acid catalyzed conditions following the procedure reported by Shaw et al 22 for GMA bulk polymer. The choice of relatively weakly acidic conditions was made on the basis of the limited pH stability range of the anchoring Si–O–C bond used to attach the ATRP initiator to the silica phase.…”

Section: Resultsmentioning

confidence: 99%

“…Ring‐opening hydrolysis of the remaining, non‐reacted oxirane groups was done under acetic acid catalysed condition, following largely the procedure of Shaw et al . 22. To verify that the applied conditions actually led to hydrolysis of the oxirane groups, GMA monomer was stirred in the 4.8 mM aqueous acetic acid solution, pH 3.0, at 60°C for 24 h and subjected to NMR analysis: 1 H NMR (360 MHz) of GMA monomer in CDCl 3 : δ H =5.55 and 6.20 (2s, 2H, CH 2 =C), 4.50 (dd, J H‐H =12.3 Hz, J H‐CH =3.1 Hz, 1H, O=C‐O‐CH 2 ), 4.10 (dd, J H‐H =12.3 Hz, J H‐CH =3.1 Hz, 1H, O=C‐O‐CH 2 ), 3.30 (m, 1H, O‐CH oxirane ), 2.72 and 2.92 (dd, 2H, O‐CH 2oxirane ), 2.00 (s, 3H, CH 3 ).…”

Section: Methodsmentioning

confidence: 99%

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Tris(hydroxymethyl)aminomethane‐functionalized silica particles and their application for hydrophilic interaction chromatography

Bui

Verhage

Irgum

2010

J of Separation Science

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A new method is presented for synthesizing a highly hydrophilic silica-based material for use in hydrophilic interaction chromatography. Porous silica particles used as a starting substrate were modified with 3-bromopropyl trichlorosilane and grafted with glycidyl methacrylate by controlled ("living") atom transfer radical polymerization in order to introduce an oxirane-carrying reactive tentacle layer on the silica surface. The grafted material was thereafter subject to an oxirane ring opening reaction with tris(hydroxy-methyl)aminomethane in dimethylformamide to yield a polymer-bound equivalent of the well known and highly hydrophilic "TRIS" buffering substance. Chemical characterization was done by diffuse reflectance FT-IR, X-ray photoelectron spectroscopy, elemental analysis, and (1)H NMR. Porosity and surface area examination was done with Brunauer-Emmett-Teller. Chromatographic application of the material was evaluated by separations of nucleic bases, small organic acids, and common nucleotides under mixed hydrophilic interaction chromatography and weak anion exchange conditions.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Tris(hydroxymethyl)aminomethane‐functionalized silica particles and their application for hydrophilic interaction chromatography

Bui

Verhage

Irgum

2010

J of Separation Science

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“…The anion generated by the reaction between the amine and the epoxy ring can react with an active hydrogen present in water, alcohol, phenol or carboxyl to form a new anion. This anion is able to open a second epoxy ring continuing the curing reaction [10,[42][43][44][45][46] . Figure 7A shows the absorbed water content by the samples of F-161 prepreg samples submitted to moisture of 84, 75 and 58% at 60 °C.…”

Section: Ft-nir Spectroscopymentioning

confidence: 99%

Understanding the water uptake in F-161 glass-epoxy composites using the techniques of luminescence spectroscopy and FT-NIR

2017

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This paper investigates the application of the luminescence spectroscopy technique in steady-state to study the moisture influence in glass fiber/epoxy prepreg and their laminates. The studies were monitored by intrinsic luminescence comparing the results with gravimetric analysis and near infrared with Fourier transform. Samples are cured and submitted to humidity controlled at 60 and 80 °C until 90 days. It is verified that the decrease in the maximum emission of the samples is directly related to the material moisture content. However, for very short periods, there is an increase in the relative intensity and blue shift of the emission band for all samples treated at 60 °C, which is related to an increase of the rigidity of the polymeric matrix. The results in this paper have a great significance because it brings a wide discussion on the interaction of water in epoxy composites materials.

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“…GMA offers advantages over other (meth‐)acrylates because it is susceptible to postpolymerization chemical modifications at the oxirane ring, which makes it attractive for a wide variety of applications depending on the incorporated functionality. Insertion of different functionalities can be readily achieved by exchanging different reagents and using rather mild synthetic conditions . For instance, the hydrolysis of poly(glycidyl methacrylate) leads to the formation of glyceryl methacrylate copolymer (77 mol% 2,3‐dihydroxy units and 23 mol% 1,3‐dihydroxy units) which is soluble in water .…”

Section: Introductionmentioning

confidence: 99%

“…Insertion of different functionalities can be readily achieved by exchanging different reagents and using rather mild synthetic conditions . For instance, the hydrolysis of poly(glycidyl methacrylate) leads to the formation of glyceryl methacrylate copolymer (77 mol% 2,3‐dihydroxy units and 23 mol% 1,3‐dihydroxy units) which is soluble in water . Synthetic methods for incorporating 9‐anthracene carboxylic acid and indole groups have also been reported .…”

Section: Introductionmentioning

confidence: 99%

Kinetic and Copolymer Composition Investigations of the Free Radical Copolymerization of 1‐Octene with Glycidyl Methacrylate

Rosales‐Guzmán

Pérez‐Camacho²,

Torres-Lubián³

et al. 2018

Macro Chemistry & Physics

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Kinetic and copolymer composition investigations of the free radical copolymerization of 1‐octene with glycidyl methacrylate are reported. The chemical structure of the obtained copolymers is elucidated by 1H, 13C, heteronuclear single quantum coherence nuclear magnetic resonance (NMR) and infrared spectroscopies. 1H NMR measurements indicate that a maximum statistical incorporation of 1‐octene in the copolymer chain of 32 mol% is obtained when 90 mol% of this comonomer is used in the initial monomer feed of the copolymerization reaction. Furthermore, the reactivity ratios of this comonomer system are estimated using the obtained experimental data, which are fitted to the integral form of the copolymerization equation utilizing a nonlinear least squares approach. To the best of knowledge, this is the first report on the reactivity ratios of this specific comonomer system. To evaluate the potential of the obtained materials as dispersants, the effect of the polymer concentration on the dispersion of copper nanopowders in organic solvents is studied for a copolymer with a 1‐octene composition of 25 mol%.

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An alternative pathway for the hydrolysis of epoxy ester compounds

Cited by 26 publications

References 20 publications

Tris(hydroxymethyl)aminomethane‐functionalized silica particles and their application for hydrophilic interaction chromatography

Tris(hydroxymethyl)aminomethane‐functionalized silica particles and their application for hydrophilic interaction chromatography

Understanding the water uptake in F-161 glass-epoxy composites using the techniques of luminescence spectroscopy and FT-NIR

Kinetic and Copolymer Composition Investigations of the Free Radical Copolymerization of 1‐Octene with Glycidyl Methacrylate

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