One-Pot Synthesis of Amide-Functional Main-Chain Polybenzoxazine Precursors

Durukan, Canan; Kışkan, Barış; Yaǧcı, Yusuf

doi:10.3390/polym11040679

Cited by 18 publications

(19 citation statements)

References 61 publications

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“…It will lead to the formation of micro-voids, and damage the performance of final materials. Benzoxazine resin is generated from traditional phenolic resin which not only retains advantages of common phenolic resins, such as high thermal stability, good mechanical properties, and better electrical properties, but also has some unique properties superior to phenolic resins, such as rich molecular design flexibility, no small molecule release during the crosslinking process, close to zero volume contraction, low water absorption, and high T g and high char yield [10].…”

Section: Introductionmentioning

confidence: 99%

Benzoxazine Containing Fluorinated Aromatic Ether Nitrile Linkage: Preparation, Curing Kinetics and Dielectric Properties

Chen

Ren

et al. 2019

Polymers

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Benzoxazine containing fluorinated aromatic ether nitrile linkage (FAEN-Bz) had been synthesized from 2,6-dichlorobenzonitrile, 4,4’-(hexafluoroisopropylidene)diphenol (bisphenol AF), 3-Aminophenol, formaldehyde, phenol by condensation polymerization and Mannich ring-forming reaction. Structures of the monomer were verified by Proton NMR spectrum (1H-NMR) and Fourier transform infrared spectroscopy (FTIR). Curing behaviors and curing kinetics of designed monomers were investigated and discussed. The activation energy was calculated and possible polymerization mechanisms were also proposed. Then, properties of cured polymers including crosslinking degrees, thermal decomposition, surface wettability and energy, and dielectric properties were studied and discussed. Additionally, programmed integral decomposition temperature (IPDT) was also used to evaluate the thermal stability of final polymers. Results indicated that the incorporation of benzoxazine and nitrile resulted in increased thermal stability and char yields. Moreover, the surface wettability and dielectric properties of poly(FAEN-Bz) can be easily controlled by tuning the curing temperatures and time.

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Section: Introductionmentioning

confidence: 99%

Benzoxazine Containing Fluorinated Aromatic Ether Nitrile Linkage: Preparation, Curing Kinetics and Dielectric Properties

Chen

Ren

et al. 2019

Polymers

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“…Durukan et al synthesized three different polymers by reacting 3,4-dihydrocoumarine (DHC) and paraformaldehyde with 1,3-diaminopropane, 1,6-diaminohexane, or Jeffamine ED-900 in one pot. 18 The one-pot reaction proceeded via the ring-opening of DHC in the presence of amines. The subsequent reaction steps involved the Mannich and ring-closing reactions (cascade reactions).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of a benzoxazine monomer containing maleimide and biphenyl groups

Guo

Yang

et al. 2021

High Performance Polymers

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Benzoxazine resin exhibits excellent properties and is widely used in many fields. Herein, the synthesis of a novel compound, the bis(2,4-dihydro-2 H-3-(4- N-maleimido)phenyl-1,3-benzoxazinyl)biphenyl (BMIPBB), has been reported, which was synthesized by reacting N-(4-aminophenyl)maleimide (APMI), formaldehyde, and 4,4’-dihydroxybiphenyl. 1,3,5-three(4-(maleimido)phenyl)-1,3,5-triazine (TMIPT) was formed as an intermediate during the reaction. The proton nuclear magnetic resonance (1H-NMR) and Fourier transform-infrared (FTIR) spectroscopy experiments were conducted to determine the structure of BMIPBB. BMIPBB was obtained as a reddish-brown solid in 40.1% yield. The thermal properties of BMIPBB were investigated using differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) techniques. Analysis of the DSC curves revealed that the broad peak representing the release of curing reaction heat appeared in the temperature range of 140–330°C. The peak temperature was 242.59°C and the heat of the reaction was 393.82 J/g, indicating that the rate of the curing reaction was low and the heat of the reaction was high. Analysis of the TGA results revealed that the weight loss rate was 5% at 110°C. The monomer exhibited a significant weight loss in the range of 320–500°C. The compound lost 50% of its weight at a temperature of 427°C.

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“…Initially, primary amine functional benzoxazine monomers were synthesized as a useful intermediate for the production of various amide and polyamides. , Alternatively, an amide linkage containing mono- and difunctional benzoxazine monomers and main-chain polybenzoxazine precursor was synthesized starting from commercially available and relatively cheap 3,4-dihydrocoumarin (DHC). Besides, DHC was also used to synthesize a similar main-chain polybenzoxazine in a one-pot approach. , Apart from these syntheses, ortho -amide functional benzoxazines were designed to utilize benzoxazole formation that takes place at ca. 250 °C between the phenolic −OH and ortho -amide moiety with water elimination (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

“…Besides, DHC was also used to synthesize a similar main-chain polybenzoxazine in a one-pot approach. 47,48 Apart from these syntheses, ortho-amide functional benzoxazines were designed to utilize benzoxazole formation that takes place at ca. 250 °C between the phenolic −OH and ortho-amide moiety with water elimination (Scheme 2).…”

Section: ■ Introductionmentioning

confidence: 99%

Advanced Polymers from Simple Benzoxazines and Phenols by Ring-Opening Addition Reactions

2020

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Simple benzoxazines were mixed and reacted with various phenolics such as phenol, p-nitrophenol, p-cresol, 1,3-dihyroxybenzene (resorcinol), 1,3,5-trihydroxybenzene (phloroglucinol), and N-(2-hydroxyphenyl)benzamide. The influence of these phenolic compounds on ring-opening polymerization temperature of benzoxazines was examined by DSC analysis. The cresol-based benzoxazine (C-a) and phenolics yielded polymers with molecular weight of around 1500 Da. Interestingly, for C-a/resorcinol- and C-a/phloroglucinol-based polymers, a second GPC trace was observed that corresponds to a few million daltons for mixing ratios of 4:1 and 5:1. Moreover, the mixtures of C-a and N-(2-hydroxyphenyl)benzamide gave poly(benzoxazine–benzoxazole)s through a new methodology eliminating the need of synthesis of ortho-amide benzoxazines. The obtained polymers were soluble and characterized in detail by 1H NMR, 13C NMR, GPC, DSC, and TGA analyses.

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One-Pot Synthesis of Amide-Functional Main-Chain Polybenzoxazine Precursors

Cited by 18 publications

References 61 publications

Benzoxazine Containing Fluorinated Aromatic Ether Nitrile Linkage: Preparation, Curing Kinetics and Dielectric Properties

Benzoxazine Containing Fluorinated Aromatic Ether Nitrile Linkage: Preparation, Curing Kinetics and Dielectric Properties

Synthesis and properties of a benzoxazine monomer containing maleimide and biphenyl groups

Advanced Polymers from Simple Benzoxazines and Phenols by Ring-Opening Addition Reactions

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