Curing of epoxy resin with phosphazene derivatives.

Yamamoto, Takeshi; Takahashi, Kazuhiko; Kon, Yuhji; Harakawa, Kazuhisa

doi:10.1295/koron.45.851

Cited by 4 publications

(6 citation statements)

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“…There are two main synthetic approaches that make it possible to obtain functional phosphazenes capable of forming covalent bonds with epoxy matrices: Synthesis of organophosphazenes with reactive epoxy groups for addition to the epoxy component [ 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 ]. Synthesis of organophosphazenes with reactive amino groups for use as a hardener or its component [ 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 ]. …”

Section: Introductionmentioning

confidence: 99%

Phosphazene-Containing Epoxy Resins Based on Bisphenol F with Enhanced Heat Resistance and Mechanical Properties: Synthesis and Properties

et al. 2022

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Organophosphazenes are of interest due to the combination of increased mechanical and thermal properties of polymer materials obtained with their use, however, they are characterized by a complex multi-stage synthesis. Moreover, the high viscosity of phosphazene-containing epoxy resins (PhER) makes their processing difficult. To simplify the synthesis of PhER, a one-step method was developed, and bisphenol F was chosen, which also provided a decrease in viscosity. In the current study, PhER were formed by a one-stage interaction of hexachlorocyclotriphosphazene (HCP) with bisphenol F isomers and epichlorohydrin in the presence of alkali, which was a mixture of epoxycyclophosphazenes (ECPh) with a functionality from 1 to 4 according to the results of MALDI-TOF analysis. Conventional epoxy resins based on bisphenol F, also formed during the process, showed high mechanical properties and glass transition temperature, and the reactivity of the obtained resins is similar to the base epoxy resins based on bisphenols A and F. Cured PhER had higher or the same mechanical properties compared to base epoxy resins based on bisphenol A and F, and a glass transition temperature comparable to base epoxy resins based on bisphenol F: glass transition temperature (Tg) up to 174.5 °C, tensile strength up to 74.5 MPa, tensile modulus up to 2050 MPa, tensile elongation at break up to 6.22%, flexural strength up to 146.6 MPa, flexural modulus up to 3630 MPa, flexural elongation at break up to 9.15%, and Izod impact strength up to 4.01 kJ/m2. Analysis of the composition of the obtained PhER was carried out by 1H and 31P NMR spectroscopy, MALDI-TOF mass spectrometry, X-ray fluorescence elemental analysis, and contained up to 3.9% phosphorus and from 1.3% to 4.2% chlorine. The temperature profile of the viscosity of the resulting epoxy resins was determined, and the viscosity at 25 °C ranged from 20,000 to 450,000 Pa‧s, depending on the ratio of reagents. The resins studied in this work can be cured with conventional curing agents and, with a low content of the phosphazene fraction, can act as modifiers for traditional epoxy resins, being compatible with them, to increase impact strength and elasticity while maintaining the rest of the main mechanical and processing properties, and can be used as a resin component for composite materials, adhesives, and paints.

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Section: Introductionmentioning

confidence: 99%

Phosphazene-Containing Epoxy Resins Based on Bisphenol F with Enhanced Heat Resistance and Mechanical Properties: Synthesis and Properties

et al. 2022

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“…Currently, there are 2 main synthetic approaches that allow obtaining functional phosphazenes capable of forming covalent bonds with epoxy matrices: synthesis of organophosphazenes with reactive epoxy groups [25,26,27,33,34,35,36,37,38,39,40,41,42,43,44,45,46,47,48,49,50,51,52,53,54,55] for addition to the epoxy component, and synthesis of organophosphazenes with reactive amine [56,57,58,59,60,61,62,63,64] groups for use as a hardener. However, at present, most of the processes of synthesis of functional epoxyphosphazenes described in the literature are primarily of scientific interest because of the complexity of their scaling and the large number of intermediate stages [25,33,34,35,36,37,41,42,43,45,46,47,48,50,51,52,53,54,55].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Resorcinol-Based Phosphazene-Containing Epoxy Oligomers

et al. 2019

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Phosphazene-containing epoxy-resorcinol oligomers (PERO) are synthesized in one stage with the direct interaction of hexachlorocyclotriphosphazene (HCP), resorcinol, and epichlorohydrin in the presence of solid NaOH. Depending on the initial ratio of HCP:resorcinol, PERO contains from 20 to 50 wt.% phosphazene component (2.0–4.8% of phosphorus) and have an epoxy group content up to 30 %. Products are characterized using 1H and 31P NMR spectroscopy, MALDI-TOF mass spectrometry, and elemental analysis. According to mass spectrometry, the phosphazene fractions of PERO include up to 30 individual compounds with a predominance of cyclotriphosphazenes with one unsubstituted chlorine atom and four or five glycidyl groups. PERO has a lower viscosity in comparison with similar resins based on bisphenol A, which can simplify their use as a binder for polymer composites, adhesives, and paints.

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“…(1) The synthesis of organophosphazenes with reactive epoxy groups for addition to the epoxy component ; (2) The synthesis of organophosphazenes with reactive amine groups for use as a curing agent or its component [44][45][46][47][48][49][50][51][52].…”

Section: Introductionmentioning

confidence: 99%

“…2) The synthesis of organophosphazenes with reactive amine groups for use as a curing agent or its component [44][45][46][47][48][49][50][51][52].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Bisphenol A Based Phosphazene-Containing Epoxy Resin with Reduced Viscosity

et al. 2019

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Phosphazene-containing epoxy oligomers (PEO) were synthesized by the interaction of hexachlorocyclotriphosphazene (HCP), phenol, and bisphenol A in a medium of excess of epichlorohydrin using potassium carbonate and hydroxide as HCl acceptors with the aim of obtaining a product with lower viscosity and higher phosphazene content. PEOs are mixtures of epoxycyclophosphazene (ECP) and a conventional organic epoxy resin based on bisphenol A in an amount controlled by the ratio of the initial mono- and diphenol. According to 31P NMR spectroscopy, pentasubstituted aryloxycyclotrophosphazene compounds predominate in the ECP composition. The relative content in the ECP radicals of mono- and diphenol was determined by the MALDI-TOF mass spectrometry method. The organic epoxy fraction, according to gas chromatograpy-mass spectrometry (GC-MS), contains 50–70 wt % diglycidyl ether of bisphenol A. PEO resins obtained in the present work have reduced viscosity when compared to other known phosphazene-containging epoxy resins while phosphazene content is still about 50 wt %. Resins with an epoxy number within 12–17 wt %, are cured by conventional curing agents to form compositions with flame-retardant properties, while other characteristics of these compositions are at the level of conventional epoxy materials.

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Curing of epoxy resin with phosphazene derivatives.

Cited by 4 publications

References 0 publications

Phosphazene-Containing Epoxy Resins Based on Bisphenol F with Enhanced Heat Resistance and Mechanical Properties: Synthesis and Properties

Phosphazene-Containing Epoxy Resins Based on Bisphenol F with Enhanced Heat Resistance and Mechanical Properties: Synthesis and Properties

Synthesis of Resorcinol-Based Phosphazene-Containing Epoxy Oligomers

Synthesis of Bisphenol A Based Phosphazene-Containing Epoxy Resin with Reduced Viscosity

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