Bis(4-cyanophenyl) phenyl phosphate as viscosity reducing comonomer for phthalonitrile resins

Terekhov, V.E.; Aleshkevich, V.V.; Afanaseva, Ekaterina S.; Nechausov, Sergey; Бабкин, А. В.; Bulgakov, Boris A.; Кепман, А. В.; Авдеев, В. В.

doi:10.1016/j.reactfunctpolym.2019.03.010

Cited by 24 publications

(7 citation statements)

References 49 publications

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“…Using monomers 1 and 2 in combination with reactive diluent 3 (Figure 1) recently synthesized in our lab [25] and diamine 4 (APB) as curing agent, a formulation named PNT was developed. Blended resin PNT demonstrated melt viscosity 1000 mPa•s 100 °C with plateau at temperatures higher than 150 °C with viscosity value 10 mPa•s (Figure 3).…”

Section: Resultsmentioning

confidence: 99%

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Advanced Phthalonitrile Resin Systems for Vacuum Processing

Babkin¹,

Kepman²,

Avdeev³

et al. 2020

SAMPE 2020 | Virtual Series

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Advanced phthalonitrile resin systems based on recently introduced low-melting phosphoruscontaining monomers were developed. A new class of bis-benzonitirle reactive plastisizers allowed to obtain resin systems possessing improved processability (melt viscosity < 100 mPa•s at temperatures down to 120 °C) suitable for manufacturing composites by vacuum infusion molding process or RTM at the lowest reported processing temperature of 120 °C on carbon fabric (3K HTA40, twill). The curing cycle was adjusted to achieve the best mechanical properties of the composites reaching 852 MPa in compressive strength. The influence of postcuring conditions on the resulting composites properties was established. After post-curing at 375 °C the obtained composites demonstrated up to 90% mechanical properties retention at 400 °C (τ12 = 60-80 MPa). Solvent-free phthalonitrile prepregs were developed for the first time. Prepreg consolidation yielded high-quality composites. Flame retardant properties of investigated composites demonstrated extremely high LOI > 80%. Thus easy-processable phthalonitriles for out-of-autoclave manufacturing techniques with convenient curing conditions and excellent heat resistant and flame-retardant properties were developed.

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Section: Resultsmentioning

confidence: 99%

“…Bis(3-(3,4-dicyanophenoxy)phenyl) phenyl phosphate was synthesized following the procedure described in [21]. Bis(4-cyanophenyl) phenyl phosphate was obtained as described in [25]. 3,3'-(1,3-phenylenbis(oxy))dianiline (APB) was purchased from SynAsia and used as received.…”

Section: Methodsmentioning

confidence: 99%

Advanced Phthalonitrile Resin Systems for Vacuum Processing

Babkin¹,

Kepman²,

Avdeev³

et al. 2020

SAMPE 2020 | Virtual Series

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“…An assumption was made for the results' interpretation: hydrolysis of the monomer CPP was considered as a pseudo-first-order reaction due to the sufficiently higher water concentration in experimental than the substrate's concentrations. It was established that hydrolysis passed only by 4-cyanophenol elimination [3] (Fig. 4).…”

Section: Experimental Design Materials and Methodsmentioning

confidence: 99%

Hydrolysis data for bis(4-cyanophenyl) phenyl phosphate including rate constants and activation parameters

et al. 2020

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Hydrolysis data for Bis(4-cyanophenyl) phenyl phosphate (CPP), introduced as a reactive diluent for phthalonitrile monomers, under pH 4, 7 and 10 are presented. Conversion/time plots collected by HPLC analysis, typical chromatograms and NMR spectra of the substrate and the reaction products are given. Pseudo-first order rate constants are determined for CPP at 25, 50 and 80 °C. Activation parameters were calculated from Arrhenius equation.

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“…At present, researchers basically believe that CN polymerization mainly produces triazine, isoindole and phthalocyanine rings, [31][32][33][34][35][36][37][38][39][40][41][42] does not produce small molecules, and gives the polymerization mechanism of forming the three heterocycles. However, this does not explain the experimental results in this paper very well.…”

Section: The Possible Polymerization Mechanism Of 4-apnmentioning

confidence: 99%