Ring-Opening Polymerization with Expansion in Volume

Bailey, William J.; Sun, Robert; Katsuki, Hirokazu; Endō, Takeshi; Iwama, Hideaki; Tsushima, Rikio; Saigou, Kazuhide; Bitritto, Michel M.

doi:10.1021/bk-1977-0059.ch004

Cited by 71 publications

(31 citation statements)

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“…[1][2][3][4][5][6][7][8][9] Spiroorthoesters (SOEs) are bicyclic compounds that are commonly used as expanding monomers and can be synthesized from lactones and epoxides under Lewis acid catalysis. 10,11 The use of five-member lactones, which are unable to homopolymerize for thermodynamic reasons, ensures the formation of an intermediate SOE.…”

Section: Introductionmentioning

confidence: 99%

New thermosets obtained by cationic copolymerization of DGEBA with γ‐caprolactone with improvement in the shrinkage. II. Time–temperature–transformation (TTT) cure diagram

González

Fernández‐Francos

Salla

et al. 2007

J of Applied Polymer Sci

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Mixtures of diglycidylether of bisphenol A (DGEBA) with different proportions of g-caprolactone (g-CL) were cured with ytterbium triflate as initiator. The curing was studied with differential scanning calorimetry (DSC) and thermo mechanical analysis (TMA). The results are presented in the form of a time-temperature-transformation diagram. The kinetic analysis was performed by means of the isoconversional integral procedure and the kinetic model was also determined using the Coats-Redfern method. Gelation was determined by means of combined experiences of DSC and TMA. The relationship between the glass transition temperature (T g ) and the degree of conversion a was determined by DSC. Using the isoconversional lines and the T g -a relationship, the vitrificacion curve was obtained. The methodology developed makes it possible to obtain the TTT diagram using only no-isothermal experiments with equivalent results to those using classical isothermal procedures. The addition of g-CL accelerates the curing and reduces the shrinkage after gelation and consequently the internal stresses in the material.

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Section: Introductionmentioning

confidence: 99%

New thermosets obtained by cationic copolymerization of DGEBA with γ‐caprolactone with improvement in the shrinkage. II. Time–temperature–transformation (TTT) cure diagram

González

Fernández‐Francos

Salla

et al. 2007

J of Applied Polymer Sci

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“…Therefore, it is necessary to investigate a cross-linking system which is able to counteract the usual shrinkage by curing in materials without fillers. Some spiroorthoesters, known as "expandable monomers", were the subject of the research work because these compounds polymerize with only small shrinkage or even expansion in volume 1,2) . For the first time the formation of spiroorthoesters (SOE) from the reaction of epoxides with lactones in the presence of Lewis acids was reported by Bodenbrenner 3) .…”

Section: Introductionmentioning

confidence: 99%

Cationic copolymerization of phenyl glycidyl ether with lactones. Characterization of the reaction mixture with chromatographic methods

Fedtke

Haufe

Kahlert

et al. 1998

Angew. Makromol. Chem.

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This paper refers to the influence of the catalysts boron trifluoride p‐methoxyaniline complex (BF3 · MA) and boron trifluoride etherate complex (BF3 · Et2O) having different reactivity in cationic copolymerization of phenyl glycidyl ether (PGE) with γ‐butyrolactone (γ‐BL) and ϵ‐caprolactone (ϵ‐CL), respectively. Reactions were followed by FT‐IR, HPLC and SEC. SEC with multiple detection and Two‐Dimensional‐Chromatography HPLC/SEC were used to characterize the products in view to their copolymer compositions. In the presence of BF3 · MA a preferred formation of spiroorthoesters (SOE) was observed; the polymerization of SOE under these conditions can be neglected. In case of the more reactive BF3 · Et2O the epoxide homopolymerization strongly competes with SOE formation, resulting in a product mixture of epoxide homopolymers (and in the case of ϵ‐CL also lactone homopolymers) and copolymers with low lactone content.

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“…The OSOC thus obtained was insoluble in common organic solvents due to the high crystallinity, which was arisen by the spontaneous alignment of the rigid rod‐like oligomer chains into a bundle, preventing adequate structural analyses. On the other hand, spiroorthocarbonates undergo the double ring‐opening polymerization with volume expansion . We revealed that the spiroorthocarbonate moieties in the main chain of the OSOC underwent cationic ring‐opening polymerization to give a crosslinked poly(ether carbonate) .…”

Section: Introductionmentioning

confidence: 94%

Efficient synthesis and properties of soluble aliphatic oligo(spiroorthocarbonate)s from pentaerythritol derivatives

Mori

Sudo

Endō

2019

J. Polym. Sci. Part A: Polym. Chem.

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A series of soluble oligo(spiroorthocarbonate)s (OSOCs) were synthesized by polycondensation of tetraethylorthocarbonate with pentaerythritol derivatives. The pentaerythritol derivatives used herein were synthesized from pentaerythritol by attaching substituents on it to improve the solubility of themselves and the resulting OSOCs. The structures of the OSOCs were confirmed by NMR spectroscopy and MALDI‐TOF mass analysis. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 792–798

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Ring-Opening Polymerization with Expansion in Volume

Cited by 71 publications

References 0 publications

New thermosets obtained by cationic copolymerization of DGEBA with γ‐caprolactone with improvement in the shrinkage. II. Time–temperature–transformation (TTT) cure diagram

New thermosets obtained by cationic copolymerization of DGEBA with γ‐caprolactone with improvement in the shrinkage. II. Time–temperature–transformation (TTT) cure diagram

Cationic copolymerization of phenyl glycidyl ether with lactones. Characterization of the reaction mixture with chromatographic methods

Efficient synthesis and properties of soluble aliphatic oligo(spiroorthocarbonate)s from pentaerythritol derivatives

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