The effect of aromatic diboronic acid on characteristics of polybenzoxazine based on phenol and 4-aminomethylbenzoate

Ipek, Halil; Hacaloğlu, Jale

doi:10.1007/s10965-018-1656-6

Cited by 5 publications

(8 citation statements)

References 28 publications

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“…The Bz and PBz resins were characterized with FTIR to realize how the incorporated PBA change the chemical structures of BZ, as shown in Figure 2. The peaks at 1512 and 1610 cm −1 belong to the ortho‐substituted benzene, 26 and PBA addition appears to intensify the peak at 1610 cm −1 . The peak at 930 cm −1 in the PBz 20 belongs to the hydrogen bond in the meta‐position of benzene 27 .…”

Section: Resultsmentioning

confidence: 94%

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The water uptake, thermal and mechanical properties, and aging resistance to thermo‐oxidation of phenylboronic acid‐modified benzoxazine‐glass fiber composites

Hsu

Hwang

2022

J of Applied Polymer Sci

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Polybenzoxazines, also known as Benzoxazine (Bz) is one kind of highperformance thermoset polymers. It manifests several advantages when used for thermal protection applications, such as thermal and dimensional stabilities, low rate of moisture absorption and near zero volatility in curing process. However, benzoxazine shows its drawbacks in terms of curing temperature, char yield at elevated temperature, and resin toughness. Thus, modification of Bz matrix would be essential in order to improve these unfavorable properties. In this study, a facile synthesis of phenylboronic acid-modified (PBA) benzoxazine (PBz) and glass fibers (GF) composites with varied PBA ratios were prepared. Briefly, GF fabrics were impregnated with each of Bz or PBz/acetone solution and baked to form B-staged prepregs. Then, the prepregs were stacked, molded and cured in a hot-pressing machine to form composites. The present study shows the 10 wt% PBA modified-Bz/GF composite is the optimal formulation as it exhibits minimal water uptake, enhanced char yield, decent thermomechanical stability in terms of glass transition temperature, exceptional interlaminar shear strength (ILSS) and highest flexural strength. Moreover, the PBz 10/GF composite subject to thermooxidative aging still maintains good levels of shear and flexural properties for potential service as thermal protection layer.

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Section: Resultsmentioning

confidence: 94%

“…Analogue enhancements in char yield can also be achieved by modification of Bz with other boron-containing compounds, such as borate, 21 benzodioxaborole 28 and diboronic acid. 26,31…”

Section: Thermogravimetric Analysis Of Bz and Pbzmentioning

confidence: 99%

The water uptake, thermal and mechanical properties, and aging resistance to thermo‐oxidation of phenylboronic acid‐modified benzoxazine‐glass fiber composites

Hsu

Hwang

2022

J of Applied Polymer Sci

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“…The TGA curves of the polymer samples involving AB indicated again a multistep decomposition as in case of polybenzoxazine based on aniline, yet, the char yield was increased significantly compared to polybenzoxazine based on aniline (Fig. ) . The temperature at which 5 wt % of the polymer decomposes, Td 5 , was also increased when AB was used.…”

Section: Resultsmentioning

confidence: 99%

“…Improvement in processability and thermal properties of benzoxazine resins was obtained upon incorporation of phenyl boronic acid that acted also as a catalyst during the polymerization process . Recently, in our group, polybenzoxazine composites were prepared by curing benzoxazine monomers based on phenol and aniline or p ‐amino methyl benzoate in the presence of various amounts of benzene diboronic acid . Reactions between BOH groups and phenolic hydroxyl and ester groups present in the benzoxazine monomer yielded a network structure increasing thermal stability significantly.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and analysis of thermal characteristics of polybenzoxazine based on phenol and 3‐Amino phenyl boronic acid

Ipek

Hacaloğlu

2019

J. Polym. Sci. Part A: Polym. Chem.

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In this work, 3‐amino phenyl boronic acid (AB) was used as an aniline derivative in the preparation of polybenzoxazine based on phenol. In order to investigate the effect of boronic acid on thermal characteristics, polybenzoxazines based on pure aniline and 50% aniline and AB mixture were also prepared and analyzed. Significant improvements in thermal characteristics, increase in thermal stability and char yield, was recorded for the polymers based on AB or its mixture. This behavior was associated with crosslinked structures generated by condensation reactions of BOH groups. Morphologic and thermal characteristics of polybenzoxazines samples were investigated by NMR, FTIR, DSC, TGA, and direct pyrolysis mass spectrometry (DP‐MS) techniques. Application of DP‐MS technique also supplied additional information on crosslinked structures produced by boronic acid units. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 1711–1716

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“…Additional strategies have been developed to achieve this goal, such as the incorporation into monomers of additional functional groups (such as imides) [8,9], other polymerizable groups [10][11][12], and inorganic moieties (hybrid monomers) [13,14]. The copolymerization with other resins of high crosslink density [15] or the incorporation of additives increasing external hydrogen bonds [16] have also been studied. In general, after thermal curing, monobenzoxazines give weakly crosslinked small oligomers with molecular weights usually below 2000 Da.…”

Section: Introductionmentioning

confidence: 99%

Highly Crosslinked Polybenzoxazines from Monobenzoxazines: The Effect of Meta-Substitution in the Phenol Ring

et al. 2020

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It is possible to control the crosslink density of polymers derived from monobenzoxazines by switching the type of substituents in the phenolic ring and their relative position with respect to the phenol group. We prepared several substituted monobenzoxazines in the para and meta positions of the phenolic ring and studied how these substituents affected the polymerization temperature of monomers and the thermal stability of the final polymers and, more extensively, how they affected the crosslink network of the final polymers. Gel content and dynamic mechanical analysis confirm that ortho- and para-orienting substituents in the meta position generate highly crosslinked materials compared to para ones. This fact can lead to the design of materials with highly crosslinked networks based on monobenzoxazines, simpler and more versatile monomers than the commercial bisbenzoxazines currently in use.

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The effect of aromatic diboronic acid on characteristics of polybenzoxazine based on phenol and 4-aminomethylbenzoate

Cited by 5 publications

References 28 publications

The water uptake, thermal and mechanical properties, and aging resistance to thermo‐oxidation of phenylboronic acid‐modified benzoxazine‐glass fiber composites

The water uptake, thermal and mechanical properties, and aging resistance to thermo‐oxidation of phenylboronic acid‐modified benzoxazine‐glass fiber composites

Synthesis and analysis of thermal characteristics of polybenzoxazine based on phenol and 3‐Amino phenyl boronic acid

Highly Crosslinked Polybenzoxazines from Monobenzoxazines: The Effect of Meta-Substitution in the Phenol Ring

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