Addition-curable phthalonitrile-functionalized novolac resin

Zhang, Bo‐xing; Luo, Zhenhua; Zhou, Hang; Liu, Feng; Yu, Ruilian; Pan, Yuexiu; Wang, Yun; Zhao, Tong

doi:10.1177/0954008312440715

Cited by 26 publications

(18 citation statements)

References 32 publications

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“…Phthalonitrile polymers offer many attractive features including outstanding thermo-oxidative stability, excellent mechanical properties, low water absorptivity and superior flame resistance [1][2][3][4][5][6][7].…”

Section: Introductionmentioning

confidence: 99%

Mechanistic and kinetic aspects of the curing of phthalonitrile monomers in the presence of propargyl groups

Augustine

Mathew

Nair

2015

Polymer

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Section: Introductionmentioning

confidence: 99%

Mechanistic and kinetic aspects of the curing of phthalonitrile monomers in the presence of propargyl groups

Augustine

Mathew

Nair

2015

Polymer

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“…Solution 1 H NMR spectra were recorded on an Agilent DD2 400-MR spectrometer (Santa Clara, California, USA) using DMSO-d 6 and CDCl 3 as solvents with respect to tetramethylsilane as the internal standard. For APN and HPN, Fourier transform infrared (FTIR) spectra were recorded with a PerkinElmer Spectrum TWO spectrometer (Waltham, Massachusetts, USA) in the solid state as potassium bromide pellets.…”

Section: Characterizationmentioning

confidence: 99%

“…[6][7][8][9][10] However, these resins also exhibit some distinct limitations in that they are extremely difficult to polymerize, requiring several days at elevated temperature before gelation occurs. Despite a high temperature of approximately 350 C and a long time of approximately 20 h, it is still hard to observe polymerization.…”

Section: Introductionmentioning

confidence: 99%

A new resin with improved processability and thermal stability

Sheng

Zeng

Xing

et al. 2016

High Performance Polymers

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To maintain outstanding thermal stability, amino-and hydroxyl-containing phthalonitrile monomers, 4-(4-aminophenoxy)-phthalonitrile (APN) and 4-(4-hydroxyphenoxy)-phthalonitrile (HPN) were selected and synthesized. Their structures were confirmed by proton nuclear magnetic resonance spectroscopy. Their curing polymers were characterized by Fourier transform infrared spectroscopy. The self-catalytic curing behaviors of the monomers were investigated by differential scanning calorimetry (DSC) at different heating rates. From the results, APN exhibits a higher curing temperature, while HPN exhibits a longer curing time. Then, mixtures of these monomers were investigated by DSC. The result shows that the 50/50 mixture exhibits different autocatalytic behaviors: the curing temperature is lower than that of APN and the curing time of the mixture is shorter than that of HPN. Furthermore, thermogravimetric analysis shows that the polymer from the mixture exhibits higher temperature of 5% weight loss (T 5% ) and char yield value at 800 C than those of the polymers from each monomer. All these results indicate that the new mixture resin exhibits improved processability with excellent thermal stability, attributed to the synergistic effect between similar monomers; the synergistic effect optimizes the cure reaction kinetics and promotes cross-linking reactions, thereby producing an excellent resin; this approach is a new method for improving the processability without sacrificing thermal stability.

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“…Novolac‐phthalonitrile resin is a self‐catalyzed phthalonitrile resin with the novolac backbone, which combines the advantages of both novolac resins and phthalonitrile resins . The phenolic hydroxyl groups of novolac can act as the curing agent for phthalonitrile moieties grafted on the novolac backbone, thus making the novolac‐phthalonitrile a self‐catalyzed resin.…”

Section: Introductionmentioning

confidence: 99%

Preparation and characterization of a self‐catalyzed fluorinated novolac‐phthalonitrile resin

Guo

Wang

et al. 2018

Polymers for Advanced Techs

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A self-catalyzed fluorinated novolac-phthalonitrile resin was synthesized by nucleophilic substitution reaction between fluorinated novolac oligomer and 4-nitrophthalonitrile. Structure of the final product was characterized by Fourier transform infrared spectroscopy and proton nuclear magnetic resonance. With the introduction of fluorine into the backbone, the fluorinated novolac-phthalonitrile presented elevated performance. Compared with the analogous novolac-phthalonitrile resin, the dielectric constant of the cured fluorinated resin decreased from 3.30 to 3.15, and the dielectric loss effectively decreased from 0.012 to 0.004 at the frequency of 1 MHz. Furthermore, the fluorinated novolac-phthalonitrile resin possessed a broader processing window and higher thermo-oxidative stability than the analogous novolac-phthalonitrile resin. Consequently, the fluorinated novolacphthalonitrile resin may be a good candidate for matrix of high performance composite in electronic and aerospace industries. KEYWORDS dielectric properties, fluorinated, phthalonitrile, thermo-oxidative property 1 | INTRODUCTION Thermosetting resin-based composites are widely used in electronic and aerospace industries because of their excellent comprehensive properties including mechanical properties, thermal stability, and corrosion resistance. Recently, they are supposed to present some functional properties, such as thermal protection, wave transparent function, wave absorption function, and damping for advanced technology field.Phthalonitrile resins, as excellent candidates for composites matrix, have drawn the attention of researchers since the 1980s. [1][2][3][4] As reported, phthalonitrile resins exhibit several outstanding properties, such as superior thermal and thermo-oxidative stability, high glass transition temperature, excellent high-temperature mechanical properties, as well as moisture resistance. [5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] The superior comprehensive properties mainly come from the abundant aromatic and heterocyclic structure of phthalonitrile resins. In addition, polymerization of phthalonitrile occurs via cyclic addition reaction, releasing no volatiles, which facilitates the high-quality products manufacturing.However, the curing reactivity of phthalonitrile is low. To promote the polymerization, curing agents such as organic amines, strong organic acids, strong organic acid/amine salts, and phenol are commonly used. [21][22][23] However, the catalysts tend to volatilize or decompose during the curing process, as well as deteriorate the thermal stability of the resin. Therefore, efforts have been devoted in the study on self-catalyzed phthalonitrile. Phthalonitrile resins containing aromatic amine, amide, and phenolic hydroxyl have been developed, 24-28 which possess good curing activity and excellent thermal stability.Novolac-phthalonitrile resin is a self-catalyzed phthalonitrile resin with the novolac backbone, which combines the advantages of both novolac resins and phthalonitrile resins...

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Addition-curable phthalonitrile-functionalized novolac resin

Cited by 26 publications

References 32 publications

Mechanistic and kinetic aspects of the curing of phthalonitrile monomers in the presence of propargyl groups

Mechanistic and kinetic aspects of the curing of phthalonitrile monomers in the presence of propargyl groups

A new resin with improved processability and thermal stability

Preparation and characterization of a self‐catalyzed fluorinated novolac‐phthalonitrile resin

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