Phenolic materials via ring‐opening polymerization: Synthesis and characterization of bisphenol‐A based benzoxazines and their polymers

Ning, Xin; Ishida, Hatsuo

doi:10.1002/pola.1994.080320614

Cited by 935 publications

(812 citation statements)

References 6 publications

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“…In Figure 9, the intensity characteristic absorption band at 1478 cm -1 was assigned to the in-plane C-H stretching of the tetra-substituted benzene, indicating that the methylene bridges formed in the free ortho positions of the phenolic structures [26,27]. Meanwhile, the characteristic band of oxazine at around 967 cm -1 did not appear in the spectra, confirming oxazine rings were involved into the polymerization at 160°C.…”

Section: Structures Of Ba-ph/bpa Pre-polymers and Polymersmentioning

confidence: 93%

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: Structures Of Ba-ph/bpa Pre-polymers and Polymersmentioning

confidence: 93%

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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“…Bisphenol-A-based benzoxazine (Ba) was prepared according to previous research. [3] 1,3-PBO was synthesized according to our previous work. [14] The chemical structures of Ba and 1,3-PBO are shown in Figure 1.…”

Section: Methodsmentioning

confidence: 99%

“…They exhibit outstanding properties such as good mechanical performance, high thermal stability, no strong acid catalysts or additives requirement for curing, low water adsorption, and near zero volumetric shrinkage upon curing, etc. [3][4][5][6][7] Benzoxazine ring is to be stable at low temperature, but a ring-opening reaction occurs at high temperature, when both the phenolic hydroxyl group and tertiary amine group are produced. High curing temperature and inherently brittle are limited to the application of benzoxazine.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of a new reactive hyperbranched polyphosphate ester, and its modification on benzoxazine-bisoxazoline resins

Wang

Tao

2014

Designed Monomers and Polymers

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A new reactive hyperbranched polyphosphate ester (HPPE) was synthesized by one step reaction. The structure of HPPE was characterized by 1 H NMR, FTIR, and inherent viscosity. High performance flame retardant modified benzoxazinebisoxazoline resins were obtained by the additional reaction with HPPE. Differential scanning calorimetry showed that there was an obvious shift in the exothermic peak of BPH5 (mass ratio of Ba-1,3-PBO and HPPE was 95:5) from 225 to 202°C, comparing with that of BPH0 (pure benzoxazine-bisoxazoline resins). It meant that the curing reaction could be catalyzed and accelerated by HPPE. The impact strength experiments illustrated that the maximum impact strength of modified resins may reach 19.2 kJ/m 2 . The char yield at 700°C of BPH5, BPH15, and BPH30 were 3.34, 4.47, and 7.75%, respectively. The benzoxazine-bisoxazoline resins modified by HPPE showed good flame retardancy.

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“…1,3-Benzoxazines are a class of heterocyclic compounds capable of undergoing ROP to give the corresponding polymers, 4-7 which surpass conventional materials in mechanical strength, thermal stability, and durability under humid environment, 8,9 particularly when the polymers are crosslinked and thus endowed with networked structures. 10 Because of these properties, 1,3-benzoxazine has attracted much attention in the material science as a hopeful candidate of next generation materials for the aerospace application.…”

Section: Benzoxazines: a New Class Of Monomers For Networked Polymermentioning

confidence: 99%

Development and application of novel ring‐opening polymerizations to functional networked polymers

Endō

Sudo

2009

J. Polym. Sci. A Polym. Chem.

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This Highlightgives an overview of the recent progress in development of new ring-opening polymerizations (ROPs) and their applications to functional networked polymers in our group. The described ROPs involve thermally induced polymerization of 1,3-benzoxazine, anionic alternating copolymerizations of epoxides and lactones, and those exhibiting equilibrium nature. These ROPs were successfully applied to the syntheses of the relevant networked polymers, leading to their distinctive features such as high thermal stability, small volume shrinkage, and selective decrosslinking ability, which enabled design and development of next generation materials.

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Phenolic materials via ring‐opening polymerization: Synthesis and characterization of bisphenol‐A based benzoxazines and their polymers

Cited by 935 publications

References 6 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 a new reactive hyperbranched polyphosphate ester, and its modification on benzoxazine-bisoxazoline resins

Development and application of novel ring‐opening polymerizations to functional networked polymers

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