Synthesis, cationic polymerization and curing reaction with epoxy resin of 3,9-di(p-methoxybenzyl)-1,5,7,11-tetra-oxaspiro(5,5)undecane

Pan, Chen; Yuan, Jinying; Bai, Ruke

doi:10.1002/(sici)1097-0126(200001)49:1<74::aid-pi296>3.0.co;2-k

Cited by 6 publications

(4 citation statements)

References 5 publications

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“…One possible attack site that has been recognized in the literature for TOSU homopolymerization is shown in step 1 of Scheme , although this has been observed only for five‐membered TOSU rings 3, 5. This linear ether attack mechanism was eliminated from consideration for six‐membered rings by integrated proton peak sizes and the inability to isolate a cyclic carbonate byproduct with both high‐performance liquid chromatography (HPLC) and gas chromatography 4. The attacking nucleophile could be BADGE as well as TOSU monomer (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…Several studies have suggested that the polymerization of bicyclic materials such as 1,5,7,11‐tetraoxaspiro[5.5]undecane (TOSU or I ) or its derivatives results in expansion upon polymerization due to a presumed ring opening mechanism in which two bonds break for each bond created 2–12. The homopolymer product formed from unsubstituted TOSU is a linear polymer lacking rigidity and resistance to dissolution in aggressive solvents.…”

Section: Introductionmentioning

confidence: 99%

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Matrix‐assisted laser desorption/ionization time‐of‐flight analysis of the copolymerization reaction of an expanding monomer with a diepoxide

Miller

Holder

Guthrie

et al. 2005

J. Polym. Sci. A Polym. Chem.

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In search of a composite with low stress and low shrinkage properties, this study includes matrix‐assisted laser desorption/ionization time‐of‐flight analysis of the photoinitiated cationic polymerization between an expanding monomer [1,5,7,11‐tetraoxaspiro[5.5]undecane (TOSU)] and a diepoxide [bisphenol A diglycidyl ether (BADGE)]. Past studies using NMR and differential scanning calorimetry analyses concluded copolymerization indirectly on the basis of deviations from homopolymer product data. This is the first study to provide direct evidence of copolymerization between these species. Unlike previous research, this study enables the identification of the TOSU homopolymer and the absence of the BADGE homopolymer, suggesting initial cationic activation of TOSU. In addition to peaks that correspond to the presumed mechanism for six‐membered TOSU polymerization, many peaks have a net gain or loss of cyclic carbonate in support of a new polymerization mechanism participating in the reaction. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 43: 5962–5970, 2005

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Matrix‐assisted laser desorption/ionization time‐of‐flight analysis of the copolymerization reaction of an expanding monomer with a diepoxide

Miller

Holder

Guthrie

et al. 2005

J. Polym. Sci. A Polym. Chem.

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“…The oxirane conversion (α) was calculated according to eq. (1):33 where subscripts 0 and t represent preirradiation and postirradiation, respectively.…”

Section: Methodsmentioning

confidence: 99%

Photopolymerization of a novel tetraoxaspiroundecane and silicon‐containing oxiranes

Chappelow

Pinzino

Chen

et al. 2006

J of Applied Polymer Sci

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New multifunctional silorane-based systems were investigated, with respect to their photoreactivity, as potential matrix resins for low-shrinkage/stress dental composites. The objective of this investigation was to synthesize and evaluate the reactivity of a silicon-analogue oxaspirocyclic monomer with silorane-based matrix resin systems during visible-light polymerization. The experimental formulations contained (1) a silicon-containing 1,5,7,11-tetraoxaspiro[5.5]undecane (TOSU-IV), (2) a phenylmethylsilane containing two cyclohexyloxiranyl groups, (3) a cyclotetrasiloxane containing four cyclohexyloxiranyl groups, and (4) a photocationic initiator system. Three main aspects were studied: (1) the photoreactivity of the tetraoxaspiroundecane (TOSU)/silorane reactant mixtures with differential scanning photocalorimetry, (2) oxirane ring-opening reactions of siloranes during binary photopolymerization with Fourier transform infrared (FTIR), and (3) oxaspirocyclic ring-opening reactions of the TOSU reactant during homophotopolymerization and binary photopolymerization with FTIR and NMR. A diallyl ether precursor of TOSU-IV was also included in selected studies. The main findings were as follows: (1) a feasible route for the successful synthesis of a silicon analogue (TOSU-IV) was developed; (2) TOSU-IV was compatible and photoreactive, making possible the reduction of polymerization stress in silorane-based matrix resins; and (3) spectroscopic evidence for both oxirane and oxaspirocyclic ring opening during the visible-light photopolymerization of the test formulations was found.

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“…239 The conversion of the epoxy groups increases as the content of the spiroorthocarbonate increases. The cationic curing reaction of a bisphenol A-type epoxy resin in the presence of a spiroorthocarbonate can be performed with borontrifluoride dietherate.…”

Section: Cationic Polymerizationmentioning

confidence: 99%

Epoxy Resins

Fink

2005

Reactive Polymers Fundamentals and Applications

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Synthesis, cationic polymerization and curing reaction with epoxy resin of 3,9-di(p-methoxybenzyl)-1,5,7,11-tetra-oxaspiro(5,5)undecane

Cited by 6 publications

References 5 publications

Matrix‐assisted laser desorption/ionization time‐of‐flight analysis of the copolymerization reaction of an expanding monomer with a diepoxide

Matrix‐assisted laser desorption/ionization time‐of‐flight analysis of the copolymerization reaction of an expanding monomer with a diepoxide

Photopolymerization of a novel tetraoxaspiroundecane and silicon‐containing oxiranes

Epoxy Resins

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