Thermal properties of phthalonitrile functional polybenzoxazines

Brunovska, Zdenka; Lyon, Richard E.; Ishida, Hatsuo

doi:10.1016/s0040-6031(00)00388-9

Cited by 167 publications

(138 citation statements)

References 15 publications

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“…[32][33][34][35][36][37] The thermograms of polybenzoxazines based on alkyl-substituted aryl amines and bisphenol-A are presented and discussed. [38] The polymerization of the benzoxazine monomer takes place through the opening of the heterocyclic ring or through the elimination of the imines from the benzoxazine ring, followed by the polymerization of the active species liberated.…”

Section: Tg Studies: Thermal Stability Of Polybenzoxazinesmentioning

confidence: 99%

Structurally diverse benzoxazines: synthesis, polymerization, and thermal stability

Vijayakumar¹,

Rishwana²,

Surender³

et al. 2013

Designed Monomers and Polymers

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Bisphenol-A is converted to indane bisphenol and spirobiindane bisphenol. The compounds bisphenol-A benzoxazine (BAB), indane bisphenol benzoxazine (IBPB), and spirobiindane bisphenol benzoxazine (SBIB) are prepared by condensing the respective bisphenols with paraformaldehyde and aniline. The structural characterization of the synthesized materials is done by using FTIR, 1 H, and 13 C NMR. Curing behavior of these benzoxazines and glass transition temperature for polybenzoxazines are studied using differential scanning calorimeter (DSC). The curing exotherm of these benzoxazines is much influenced by the nature of the aromatic unit present in the chosen bisphenol. Compared to the aromatic nucleus in BAB, the indane nucleus present in IBPB shifts the cure exotherm to lower temperatures, whereas the biindane moiety present in SBIB shifts the same to high temperatures. These benzoxazines are thermally cured both at the onset and at the peak maximum of the curing exotherm. The thermal stability of these cured materials is investigated using thermogravimetry. The nature of the aromatic nucleus present in the bisphenol and the temperature at which the curing is done decide the glass transition temperature and thermal stability of the polybenzoxazine.

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Section: Tg Studies: Thermal Stability Of Polybenzoxazinesmentioning

confidence: 99%

Structurally diverse benzoxazines: synthesis, polymerization, and thermal stability

Vijayakumar¹,

Rishwana²,

Surender³

et al. 2013

Designed Monomers and Polymers

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“…Then, the crude product was dissolved in DMF and precipitated into the dilute NaOH (1 mol/l). The brown precipitate was filtered through a glass filter under vacuum and dried in vacuum oven at 70°C, and the purified bisphthalonitrile containing benzoxazine (BPNBZ) was obtained, shown in Figure 1 [11]. The typical IR characteristics data: 2231 cm -1 (-CN), 1503, 951 cm -1 [12,13] (tri-substituted benzene ring that is attached with oxazine ring), 1247, 1032 cm -1 (stretch, C-O-C) [12,13], 1086, 830 cm -1 (stretch C-N-C) [12], 1420 cm -1 (CH 2 antisymmetric stretch); …”

Section: Synthesis Of the Novel Bisphthalonitrile Containing Benzoxazmentioning

confidence: 99%

“…The attractive characteristics of benzoxazine polymers include low melt viscosity, no release of volatiles during cure and no need for harsh catalysts, high thermal stability, good mechanical properties, excellent electrical properties and molecular design flexibility [14][15][16]. So in order to achieve low melt temperature of phthalonitrile, the presence of aromatic oxazine in the phthalonitrile molecular structure is necessary [11]. In this paper, we report on the synthesis of a bisphthalonitrile monomer containing benzoxazine and the properties of its polymer.…”

Section: Introductionmentioning

confidence: 99%

“…In this paper, we report on the synthesis of a bisphthalonitrile monomer containing benzoxazine and the properties of its polymer. Thermal polymerization of this monomer is relatively easy, because of the active benzoxazine ring in the backbone [8][9][10][11]. The focus of this research develops a novel bisphthalonitrile containing benzoxazine which expected that this bisphthalonitrile will contribute to the cross-link network formation by its own ring-forming polymerization.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

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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“…In order to further improve the performance of polybenzoxazine, an effective approach is the incorporation of addition curable groups into benzoxzine monomers, such as ethynyl [5][6][7], nitrile [8][9][10], propargyl [11] and allyl [12][13][14] groups. This approach has increased the cross-linking density and successfully afforded polybenzoxazines with high glass transition temperatures in comparison with classical polybenzoxazines.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of novel benzoxazines containing nitrile and allyl groups and their polymers

Zhang

2010

E-Polymers

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Abstract:A p-cyanophenol and allylamine based benzoxazine has been synthesized and characterized. This benzoxazine has nitrile and allyl functionalities that can polymerize, resulting in a highly crosslinked material. The DSC spectra of novel benzoxazine monomer reveal that incorporation of the nitrile and allyl group greatly decreases the ring-opening temperature of oxazine rings (140°C). The IR spectra of curing process indicate that the polymerization of oxazine ring accompany with the curing reaction of allyl and nitrile groups. Benzoxazine monomers with one or none of the two functionalities were also prepared to study structure effect on thermal properties of resulted polymer. The comparison of results confirms that introducing the two functionalities improved glass transition temperature (238 °C), thermal stability of polybenzoxazine (T 5% =340 °C), and char yield (57%).

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Thermal properties of phthalonitrile functional polybenzoxazines

Cited by 167 publications

References 15 publications

Structurally diverse benzoxazines: synthesis, polymerization, and thermal stability

Structurally diverse benzoxazines: synthesis, polymerization, and thermal stability

Synthesis and characterization of a novel bisphthalonitrile containing benzoxazine

Synthesis and characterization of novel benzoxazines containing nitrile and allyl groups and their polymers

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