A facile method for the preparation of aliphatic main-chain benzoxazine copolymers with high-frequency low dielectric constants

Zeng, Ming; Chen, Jiangbing; Xu, Qingyu; Huang, Yiwan; Feng, Zijian; Gu, Yi

doi:10.1039/c8py00407b

Cited by 55 publications

(30 citation statements)

References 44 publications

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“…However, poly(Dd-ddm) X main exhibited no T g before 400 °C, as seen in Figure 5, indicating that this polymeric material could be applied at a very high temperature. The values of T g of both polybenzoxazines were much higher than those for other reported thermosets derived from main-chain-type benzoxazines [30,31,32]. In addition, the initial values of storage modulus ( E ’) and modulus loss ( E ’’) at 25 °C of poly(Dd-hda) X main and poly(Dd-ddm) X main were found as 2360 and 283 MPa and 2858 and 326 MPa, respectively, suggesting the relatively higher rigidity of poly(Dd-ddm) X main .…”

Section: Resultscontrasting

confidence: 57%

Synthesis of Highly Thermally Stable Daidzein-Based Main-Chain-Type Benzoxazine Resins

et al. 2019

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In recent years, main-chain-type benzoxazine resins have been extensively investigated due to their excellent comprehensive properties for many potential applications. In this work, two new types of main-chain benzoxazine polymers were synthesized from daidzein, aromatic/aliphatic diamine, and paraformaldehyde. Unlike the approaches used synthesizing traditional main-chain-type benzoxazine polymers, the precursors derived from daidzein can undergo a further cross-linking polymerization in addition to the ring-opening polymerization of the oxazine ring. The structures of the new polymers were then studied by 1H nuclear magnetic resonance spectroscopy (NMR) and Fourier-transform infrared spectroscopy (FT-IR), and the molecular weights were determined by using gel permeation chromatography (GPC). We also monitored the polymerization process by differential scanning calorimetry (DSC) and in situ FT-IR. In addition, the thermal stability and flame-retardant properties of the resulting polybenzoxazines were investigated using TGA and microscale combustion calorimeter (MCC). The polybenzoxazines obtained in this study exhibited a very high thermal stability and low flammability, with a Tg value greater than 400 °C, and a heat release capacity (HRC) value lower than 30 J/(g K).

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Section: Resultscontrasting

confidence: 57%

Synthesis of Highly Thermally Stable Daidzein-Based Main-Chain-Type Benzoxazine Resins

et al. 2019

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“…The first solution is based on monomer design with selected functional groups to effect the polymerization rate and also reduce the temperature. Suitable phenols, primary amines, and formaldehyde are the components of benzoxazine synthesis, and there are many commercially available phenols and primary amines, which facilitate a high design flexibility . Several benzoxazine monomers were synthesized in this context, and different degrees of accomplishments were obtained to reduce cure temperatures …”

Section: Introductionmentioning

confidence: 99%

Counterion Effect of Amine Salts on Ring‐Opening Polymerization of 1,3‐Benzoxazines

Akkus

Kışkan

Yaǧcı

2018

Macro Chemistry & Physics

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The effect of nucleophilicity of counterions of amine HX salts as catalysts on the ring‐opening polymerization (ROP) of 1,3‐benzoxazines is investigated. The significant reduction observed for the ROP temperature is related to the nucleophilicity of counterions and found to show a general trend as I− > Br− > Cl−, as studied by differential scanning calorimetry and Fourier transform infrared spectroscopy. Moreover, the latent character of the amine salts is also demonstrated by tracking the benzoxazine–amine salt mixtures using 1H NMR spectroscopy. The spectral analysis gives evidences for the dormant nature of the amine HX salts toward benzoxazine at room temperature in solvent. Besides, thermal stabilities of the cured benzoxazine monomers with and without catalysts are investigated by thermogravimetric analysis.

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“…Benzoxazines, a new type of phenolic resins, consist in a heterocyclic six‐membered oxazine ring fused to a benzene ring, which can cationic ring opening to produce corresponding polymers . Benzoxazine monomer itself has an ultrahigh residual carbon yield, can be used as a carbon source for the IFR system, and acts as a skeleton of the carbon layer during combustion . Meanwhile, various types of benzoxazine monomer can be synthesized using various phenols and amines with different substitution groups attached; its superb molecular design flexibility allows to tailor properties of the polymerized materials in a wide range for the specific requirements of individual applications …”

Section: Introductionmentioning

confidence: 99%

“…12,13 Benzoxazine monomer itself has an ultrahigh residual carbon yield, can be used as a carbon source for the IFR system, and acts as a skeleton of the carbon layer during combustion. 14,15 Meanwhile, various types of benzoxazine monomer can be synthesized using various phenols and amines with different substitution groups attached 16 ; its superb molecular design flexibility allows to tailor properties of the polymerized materials in a wide range for the specific requirements of individual applications. 17 Silane-coupling agents can promote the adhesion between inorganic filler and polymeric resin, which is beneficial to improve the mechanical properties of the composites.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of siloxane‐containing benzoxazine and its synergistic effect on flame retardancy of polyoxymethylene

Feng

Kang

et al. 2019

Polymers for Advanced Techs

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A type of trialkoxysilane‐containing naphtholoxazine compound (Naph‐boz) was successfully synthesized and combined with ammonium polyphosphate/melamine (APP/ME) as an intumescent flame retardant (IFR) to improve the flame‐retardant efficiency of polyoxymethylene (POM). The Underwriters Laboratories 94 (UL94) vertical burning test, limiting oxygen index (LOI), cone calorimeter, thermogravimetric analysis (TGA), scanning electron microscopy (SEM), and Raman spectral analysis were used to study the flame‐retardant properties and related mechanism. The results showed that the formulation with 20 wt.% of APP, 6 wt.% of ME, and 4 wt.% of Naph‐boz passed UL94 V‐1 rating, and the LOI value was improved to 40.3%. Compared with pure POM, the IFR with Naph‐boz had greater reduction in peak heat release rate (lower 74.9%) and total heat release (lower 40.2%). SEM images showed that compact and reinforcing charred layer was formed during the POM/IFR/4Naph‐boz samples combustion, which was beneficial at reducing and maintaining low combustion parameters throughout the cone calorimeter test. The synergistic flame‐retardant effect between Naph‐boz and APP/ME was considered as the reason for the improvement in flame retardancy POM. Furthermore, because of the Naph‐boz was conducive to the compatibility between the flame retardants and matrix, the notched Izod impact strength of POM/IFR/4Naph‐boz composite was higher than that of POM/IFR system.

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A facile method for the preparation of aliphatic main-chain benzoxazine copolymers with high-frequency low dielectric constants

Abstract: The effects of the reaction solvent on the preparation, polymerization kinetics, and high-frequency dielectric properties of aliphatic main-chain benzoxazine copolymers were investigated.

Cited by 55 publications

References 44 publications

Synthesis of Highly Thermally Stable Daidzein-Based Main-Chain-Type Benzoxazine Resins

Synthesis of Highly Thermally Stable Daidzein-Based Main-Chain-Type Benzoxazine Resins

Counterion Effect of Amine Salts on Ring‐Opening Polymerization of 1,3‐Benzoxazines

Synthesis of siloxane‐containing benzoxazine and its synergistic effect on flame retardancy of polyoxymethylene

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