Synthesis and properties of a bisphenol A based phthalonitrile resin

Laskoski, Matthew; Dominguez, Dawn D.; Keller, Teddy M.

doi:10.1002/pola.20901

Cited by 223 publications

(208 citation statements)

References 19 publications

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“…As the only candidate to satisfy the flame standards of United States Navy (MIL-STD-2031), phthalonitrile resins have attracted increased attentions both in laboratory and industry areas, recently. However, high curing temperature (!250°C), high postcuring temperature (!375°C) and narrow processing window ("30°C) have also greatly limited their wide applications [5,6]. To solve these problems, phthalonitrile-based monomers with additional polymerisable groups such as amino, carboxyl, propargyl, oxazine, allyl, etc.…”

Section: Introductionmentioning

confidence: 99%

Effect of bisphenol-A on the structures and properties of phthalonitrile-based resin containing benzoxazine

Xu¹,

Jia²,

Liu³

2015

Express Polym. Lett.

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Abstract. Phthalonitrile and benzoxazine have been considered as high-performance materials in the field of heterocyclic chemistry. The polymerization of phthalonitrile and benzoxazine accelerated by active phenolic hydroxyl has attracted wide interests. In this work, self-promoted polymerization behavior and processability of phthalonitrile containing benzoxazine (BA-ph) with bisphenol-A (BPA) were investigated. Results revealed that BA-ph/BPA exhibited representative doublestage curing behaviors corresponding to the ring-opening polymerization of benzoxazine rings and ring-formation polymerization of nitrile groups. Compared with that of BA-ph, processability of BA-ph/BPA was improved and could be tuned by varying BPA contents, processing temperature and time. Then BA-ph/BPA/glass fiber (GF) composite laminates were prepared. In comparison with that of BA-ph/GF laminates (542 MPa and 25.8 GPa), the flexural strength and modulus were up to 789 MPa and 23.6 GPa, respectively. Moreover, double T g s were observed at temperature around 200~300°C and 300~380°C, indicating microphase separation during the polymerization of oxazine rings and nitrile groups, confirmed by the scanning electron microscopic (SEM) images. Thermal stabilities demonstrated that all BA-ph/BPA/GF composites exhibited high T 10% up to 510°C. The systematic study of BA-ph/BPA system could enrich our knowledge on phthalonitrile-based resins in industrial applications, especially in the areas which require excellent mechanical properties and high temperature resistance.

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Section: Introductionmentioning

confidence: 99%

Effect of bisphenol-A on the structures and properties of phthalonitrile-based resin containing benzoxazine

Xu¹,

Jia²,

Liu³

2015

Express Polym. Lett.

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“…Among the wide range of high-temperature resistant resin matrix composites, nitrile resin matrix composites, which possess excellent mechanical property, high-temperature resistance, abrasion resistance, flame resistance and high char yield, are widely applied in the preparation of new-style equipment [1][2]. Therefore, many researchers [3][4][5][6][7][8][9][10][11] have focused on their research of phthalic nitrile. Besides, a lot of researches [12][13][14][15] showed that phenol hydroxyl could improve the self-catalyzed property of phthalic nitrile monomer.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of 4-(2-hydroxyphenoxy) phthalic nitrile

Yang

Zhi-li

Sheng

et al. 2017

IOP Conf. Ser.: Mater. Sci. Eng.

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Abstract. 4-(2-hydroxyphenoxy) phthalic nitrile was prepared by the nucleophilic substitution reaction of catechol and 4-nitro phthalic nitrile in DMF with the existence of N 2 and K 2 CO 3 . The optimal reaction conditions were obtained as follows: the mole ratio of catechol, K 2 CO 3 and 4-nitro phthalic nitrile is 2:1:1, with the quality of the solute concentration of 0.222g/mL and reaction temperature 80°C. Consequently, the yield of final product reached 87.64%, and the structure of the 4-(2-hydroxyphenoxy) phthalic nitrile was characterized by IR, 1 H NMR and DSC. IntroductionWith the development of aerospace industry, the high-temperature resistant resin matrix composites have attracted a lot of attentions owing to their promising applications in aerospace manufacturing. Among the wide range of high-temperature resistant resin matrix composites, nitrile resin matrix composites, which possess excellent mechanical property, high-temperature resistance, abrasion resistance, flame resistance and high char yield, are widely applied in the preparation of new-style equipment [1][2]. Therefore, many researchers [3][4][5][6][7][8][9][10][11] have focused on their research of phthalic nitrile. Besides, a lot of researches [12][13][14][15] showed that phenol hydroxyl could improve the self-catalyzed property of phthalic nitrile monomer. However, at present, many researches about this resin monomer are mainly at the stage of laboratory research. One important reason is the lack of basic data for extensive industrial application. In this paper, we used the catechol and 4-nitro phthalic nitrile to synthesize 4-(2-hydroxyphenoxy) phthalic nitrile, and the structure was characterized by

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“…There has been increasing interest in phthalonitrile polymers [1][2][3][4][5][6][7], owing to their excellent thermal and thermo-oxidative stability, high char yield, good chemical inertness, abrasion resistance, and flame resistance. But, there are several challenges to overcome with regard the processing of these materials with higher melting temperature and high processing temperature.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of a novel bisphthalonitrile containing benzoxazine

Cao¹,

Chen²,

Wei³

et al. 2007

Express Polym. Lett.

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Abstract. The novel bisphthalonitrile containing benzoxazine (BPNBZ) has been synthesized using bisphenol-A, 4-aminophenoxylphthalonitrile and paraformaldehyde. The structure of the monomer was supported by FTIR spectroscopy, 1 H-NMR, and 13 C-NMR spectra, which have exhibited that the reactive benzoxazine ring and cyano groups exist in molecular structure of BPNBZ. The cure reaction of BPNBZ was monitored by the disappearance of the nitrile peak and the tri-substituted benzene ring that is attached with oxazine ring peak at 2231, 951 cm -1 . The thermal polymerization of the BPNBZ was studied by differential scanning calorimetry (DSC) and dynamic rheometer. It was shown that the bisphthalonitrile containing benzoxazine had completely cured with two-stage polymerization mechanisms according to oxazine ring-opening and phthalonitrile ring-forming. The thermal decomposition behaviors of the polymer were examined by thermogravimetry analysis (TGA) in nitrogen and in air. The materials achieve char yields above 73% under nitrogen at 800°C and above 78% under air at 600°C, which exhibited the cured resin has good thermal stability and thermo-oxidative stability.

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Synthesis and properties of a bisphenol A based phthalonitrile resin

Cited by 223 publications

References 19 publications

Effect of bisphenol-A on the structures and properties of phthalonitrile-based resin containing benzoxazine

Effect of bisphenol-A on the structures and properties of phthalonitrile-based resin containing benzoxazine

Synthesis and Characterization of 4-(2-hydroxyphenoxy) phthalic nitrile

Synthesis and characterization of a novel bisphthalonitrile containing benzoxazine

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