Synthesis of benzophenone-center bisphenol-A containing phthalonitrile monomer (BBaph) and its copolymerization with P-a benzoxazine

Dayo, Abdul Qadeer; Cao, Xin-man; Cai, Wenfang; Song, Sha; Wang, Jun; Zegaoui, Abdeldjalil; Derradji, Mehdi; Xu, Yi-le; Wang, An-ran; Liu, Wenbin; Gong, Lin‐dan

doi:10.1016/j.reactfunctpolym.2017.10.016

Cited by 33 publications

(29 citation statements)

References 39 publications

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“…The result shows that the crosslinking degree of polymers increases with the increase of curing temperature and curing time, which makes the mechanical properties of Polymer 2 more excellent. The mechanical properties of the MDTP polymers are better than those of many similar phthalonitrile resins . Because of the high nitrile contents of the MDTP monomer, the crosslinking degree of polymer can be increased.…”

Section: Resultsmentioning

confidence: 99%

“…In an air atmosphere, the respective 5 % weight loss of Polymer 1 and Polymer 2 are 501.1 °C and 507.3 °C, and the 10 % weight loss are 544.4 °C and 547.9 °C, respectively. And in a nitrogen atmosphere, Polymer 1 and Polymer 2 were able to maintain a weight of 67.6 % and 70.5 % at 1000 °C, which indicates that the MDTP polymer has very excellent heat resistance, better than those of some other phthalonitrile resins reported previously . It can be found by comparison that the thermal stability of Polymer 2 is better than that of Polymer 1.…”

Section: Resultsmentioning

confidence: 99%

“…Because of the high melting point and poor processability of the first generation of phthalonitrile monomers, flexible aromatic ether segments were introduced into the molecular structure of the monomers by Keller at Naval Laboratory (NRL) . At present, aliphatic aromatic ether, poly(ether imide), poly‐(arylene ether ketone), poly‐(arylene ether) and poly‐(arylene ether nitrile) have been reported. These monomers are usually prepared by the reaction of activated dihalogenated aromatic hydrocarbons and appropriate proportions of bisphenols to form phenolic intermediates, and then end‐capped with 4‐nitrophthalonitrile.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Properties of A Low Melting Point Phthalonitrile Resin Containing High Density Nitrile Groups

et al. 2020

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A polynitrile‐based phthalonitrile monomer with a low melting point containing an alkyl center, namely, 4,4′,4′′‐ [(methanetriyltris (benzene‐4,1‐diyl)) tris (oxy)] triphthalonitrile (MDTP), is synthesized from a nucleophilic substitution reaction of 4,4′,4′′‐trihydroxytriphenylmethane and 4‐nitrophthalonitrile. The MDTP monomer is cured at different temperatures 4‐(aminophenoxy)phthalonitrile (APPH) as the curing agent to give the MDTP polymers. The MDTP monomer and polymers are characterized by Fourier Transform Infrared spectroscopy (FTIR) and Nuclear Magnetic Resonance spectroscopy (NMR). Differential Scanning Calorimetric (DSC) analysis shows that the melting point of the monomer is 103 °C and the processing window is about 128 °C. The crosslinking degree of the resin varies with curing time and temperature, which affects the properties of resin. Its glass transition temperature (Tg) is higher than 400 °C. The resin possesses excellent thermal stability and mechanical properties. It loses 5 % weight at 511.2 °C and has a storage modulus of 1611 MPa at 400 °C.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and Properties of A Low Melting Point Phthalonitrile Resin Containing High Density Nitrile Groups

et al. 2020

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“…Similar to phthalonitrile‐containing polymers, benzoxazine resins can also be applied to obtain high‐performance materials . Copolymerization of benzoxazine/phthalonitrile has been studied and the prepared copolymers can be used as high‐performance matrix in various fields . However, the copolymerization between benzoxazine and phthalonitrile could result in uneven distribution of different phases, which may weaken the mechanical and thermal properties of materials.…”

Section: Introductionmentioning

confidence: 99%

Modification of Solventless‐Synthesized Benzoxazine Resin by Phthalonitrile Group: An Effective Approach for Enhancing Thermal Stability of Polybenzoxazines

Liu

Yin

et al. 2018

Macro Chemistry & Physics

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Although the solventless method for synthesizing benzoxazine resins has the advantage of low cost, the impurities involved in the products such as oligomers and original phenols significantly weaken the properties of polybenzoxazines. Herein, the commercialized BA‐a (benzoxazine derived from bisphenol‐A, aniline, and formaldehyde) resin obtained from a solventless method is modified by phthalonitrile through the reaction between phenol groups and 4‐nitrophtahlonitrile. The structures of obtained resins have been confirmed by 1H and 13C nuclear magnetic resonance (NMR) and Fourier transform infrared (FTIR). In addition, the ring‐opening polymerization behavior of each resin has been studied by differential scanning calorimetry and in situ FTIR. Furthermore, the thermal properties of the cross‐linked thermosets were measured by thermomechanical analysis and thermogravimetric analysis. The phthalonitrile‐functionalized benzoxazine resin shows a low polymerization temperature with the maximum of exothermic peak centered at 218.7 °C, and its corresponding polybenzoxazine exhibits excellent thermal stability, with a high Td5 value (346 °C) and high char yield (42.78%).

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“…The negative effects have been recorded on the crosslink density of PN polymers when these additives are used for the curing. Therefore, to overcome these problems caused by the additives, PN monomers containing hydroxyl, amino, allyl, and benzoxazine groups has been synthesized, which can be cured in the absence of additives . This is also an effective and simple method for increasing the processability and reducing the curing temperature of PN monomers …”

Section: Introductionmentioning

confidence: 99%

Curing behavior and properties of benzoxazine‐co‐self‐promoted phthalonitrile polymers

Dayo

Wang

et al. 2018

J of Applied Polymer Sci

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A new high‐performance copolymer was successfully obtained via concerted catalysis polymerization of mono‐functional benzoxazine (P‐a) and self‐promoted 4‐aminophenoxy phthalonitrile (4‐APN) monomers. The FTIR and DSC curves of the P‐a/4‐APN in different blend ratios suggested that the monomer blends can be completely cured without the addition of curing additive. The P‐a/4‐APN copolymers were cured at relatively lower curing temperatures and time. The TGA curves revealed that the P‐a/4‐APN copolymers have good thermal stability in terms of T5, T10, and char yield. A gradual increase in the glass transition temperature (Tg) values and decline were seen in the storage modulus as the loading of 4‐APN was increased from 10 to 30 wt % in the copolymer. The SEM analyses showed that copolymer's fracture surface is dendritic, showing the stress has been dispersed to a certain extent. The study revealed that the poly(P‐a/4‐APN) copolymer have much better thermal stabilities than the poly(P‐a), and the prepared copolymer can be used as a high‐performance thermosetting resin. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 46578.

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Synthesis of benzophenone-center bisphenol-A containing phthalonitrile monomer (BBaph) and its copolymerization with P-a benzoxazine

Cited by 33 publications

References 39 publications

Synthesis and Properties of A Low Melting Point Phthalonitrile Resin Containing High Density Nitrile Groups

Synthesis and Properties of A Low Melting Point Phthalonitrile Resin Containing High Density Nitrile Groups

Modification of Solventless‐Synthesized Benzoxazine Resin by Phthalonitrile Group: An Effective Approach for Enhancing Thermal Stability of Polybenzoxazines

Curing behavior and properties of benzoxazine‐co‐self‐promoted phthalonitrile polymers

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