Catalyst-free synthesis of phosphinated poly(2,6-dimethyl-1,4-phenylene oxide) with high-Tg and low-dielectric characteristic

Lin, Ching Hsuan; Tsai, Yi Jiun; Shih, Yu Sin; Chang, Hao-Chen

doi:10.1016/j.polymdegradstab.2013.11.017

Cited by 16 publications

(6 citation statements)

References 56 publications

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“…Poly(phenylene oxides) (PPOs) are widely used as matrix resins for the production of printed circuit boards (PCBs) in the electronics industry because they can be easily synthesized and display attractive properties, including low water absorption, good resistance against acids and alkalis, and low dielectric constant ( D κ < 2.6). − However, their weak resistance to organic solvents, low glass transition temperature ( T g ) and high coefficient of thermal expansion (CTE) hinder their applications. To improve the properties of PPOs, many efforts have been made.…”

Section: Introductionmentioning

confidence: 99%

Biobased Anethole-Functionalized Poly(phenylene oxides): New Low Dielectric Materials with High T_g and Good Dimensional Stability

Wang

Tao

Zhou

et al. 2018

ACS Sustainable Chem. Eng.

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A series of modified poly(phenylene oxides) (PPOs) with low dielectric constant, high T g and good dimensional stability were developed. These polymers were synthesized by treating brominated PPOs with a biobased anethole and polymerized at a high temperature in the presence of a peroxide. When the molar ratios of anethole in the PPO were 0.2, 0.35 and 0.5, respectively, the cross-linked PPOs displayed low dielectric constants of less than 2.74 and high T g (more than 220 °C). In particular, the PPO with 0.5 molar ratio of anethole exhibited a coefficient of thermal expansion (CTE, 23.4 ppm/°C) that is comparable to copper foil (ca. 18 ppm/°C). This result indicated that the modified PPOs are suitable for the production of copper-cladded laminates in electronic industry. Moreover, compared to a commercial PPO having a T g of 153 °C and CTE of 155.8 ppm/°C, the modified PPOs with anethole units possessed a higher thermostability. Considering that PPOs are widely used in the electronics industry, this contribution offers a new approach to prepare high-performance materials using a biobased feedstock.

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Section: Introductionmentioning

confidence: 99%

Biobased Anethole-Functionalized Poly(phenylene oxides): New Low Dielectric Materials with High T_g and Good Dimensional Stability

Wang

Tao

Zhou

et al. 2018

ACS Sustainable Chem. Eng.

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“…thermoplastic PPO. As shown in scheme 1, PPO has a highly symmetric molecular structure and is treated as a high-performance amorphous engineering thermoplastic due to its excellent flame retardant, high heat distortion temperature, and outstanding dielectric properties [65][66][67][68].…”

Section: Evolution Of Ppo Prepolymers/oligomersmentioning

confidence: 99%

Recent progress on polyphenylene oxide-based thermoset systems for high-performance copper-clad laminates

Qin¹,

Yu²,

Fang³

et al. 2023

J. Phys. D: Appl. Phys.

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With the rapid development of electronic information technology in the 5G era towards high integration, short propagation delay, and elevated assembly temperatures, more academic and industrial attention has been focused on high-frequency and high-speed copper-clad laminates (CCLs). Compared with conventional polymeric matrices, thermoset polyphenylene oxide (PPO) has become one of the most attractive resins applied in high-performance CCLs (HPCCLs) because of its excellent comprehensive properties, including outstanding dielectric properties, high thermal stability, great processibility, and low moisture absorption, etc. This review focuses on the history of the development of PPO prepolymers/oligomers, PPO-based thermoset resin systems, and PPO/inorganic filler composites to optimize the dielectric constant, dielectric loss, thermal conductivity, coefficient of thermal expansion, and mechanical properties. Moreover, some current challenges of PPO-based thermoset systems have been identified, such as developing feasible solutions to ensure the anti-aging properties for long-term reliability under harsh environments of high temperature, high humidity, and even high-frequency electromagnetic radiation. In general, more in-depth investigations of PPO-based thermoset systems for HPCCLs are required in the future.

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“…In a separate study, Lin et al prepared phosphinated poly(2,6-dimethyl-1,4-phenylene oxide) with varying phosphorus contents through nucleophilic substitution of brominated PPO with DOPO. Excessive use of DOPO ensured its incorporation into the pendant methyl groups on the PPO and the experimental data revealed enhanced solubility and flame retardancy without compromising its thermal and dielectric properties [ 22 ]. An alternative method for the preparation of DOPO-containing PPO involved the modification of hydroxyl-terminated poly(2,6-dimethyl-1,4-phenylene oxide) by reacting it with 4-fluoroacetophenone to form a diketone (2,6-dimethylphenyl ether) oligomer.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of DOPO-Containing Poly(2,6-dimethyl-1,4-phenylene oxide)s by Oxidative Coupling Polymerization

Lu,

Chang,

Huang

et al. 2024

Polymers

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A set of polyphenylene oxides incorporating DOPO (9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide) functionality, denoted as DOPO−R−PPO, was synthesized by copolymerization of 2,6-dimethylphenol (2,6-DMP) with various DOPO-substituted tetramethyl bisphenol monomers. In the initial step, a Friedel–Crafts acylation reaction was employed to react 2,6-DMP with different acyl chlorides, leading to the formation of ketone derivatives substituted with 2,6-dimethylphenyl groups. Subsequently, the ketones, along with DOPO and 2,6-DMP, underwent a condensation reaction to yield a series of DOPO-substituted bisphenol derivatives. Finally, polymerizations of 2,6-dimethylphenol with these DOPO-substituted bisphenols were carried out in organic solvents using copper(I) bromide/N-butyldimethylamine catalysts (CuBr/DMBA) under a continuous flow of oxygen, yielding telechelic PPO oligomers with DOPO moieties incorporated into the polymer backbone. The chemical structures of the synthesized compounds were characterized using various analytical techniques, including Fourier transform infrared spectroscopy (FTIR), proton nuclear magnetic resonance (1H NMR), phosphorus nuclear magnetic resonance (31P NMR), differential scanning calorimetry (DSC), and thermogravimetric analysis (TGA). When compared to conventional poly(2,6-dimethyl-1,4-phenylene oxide)s with a similar molecular weight range, all DOPO−PPOs exhibited higher glass transition temperatures, enhanced thermal degradability, and increased char yield formation at 800 °C without compromising solubility in organic solvents.

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Catalyst-free synthesis of phosphinated poly(2,6-dimethyl-1,4-phenylene oxide) with high-Tg and low-dielectric characteristic

Cited by 16 publications

References 56 publications

Biobased Anethole-Functionalized Poly(phenylene oxides): New Low Dielectric Materials with High T_g and Good Dimensional Stability

Biobased Anethole-Functionalized Poly(phenylene oxides): New Low Dielectric Materials with High T_g and Good Dimensional Stability

Recent progress on polyphenylene oxide-based thermoset systems for high-performance copper-clad laminates

Synthesis and Characterization of DOPO-Containing Poly(2,6-dimethyl-1,4-phenylene oxide)s by Oxidative Coupling Polymerization

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Catalyst-free synthesis of phosphinated poly(2,6-dimethyl-1,4-phenylene oxide) with high-Tg and low-dielectric characteristic

Cited by 16 publications

References 56 publications

Biobased Anethole-Functionalized Poly(phenylene oxides): New Low Dielectric Materials with High Tg and Good Dimensional Stability

Biobased Anethole-Functionalized Poly(phenylene oxides): New Low Dielectric Materials with High Tg and Good Dimensional Stability

Recent progress on polyphenylene oxide-based thermoset systems for high-performance copper-clad laminates

Synthesis and Characterization of DOPO-Containing Poly(2,6-dimethyl-1,4-phenylene oxide)s by Oxidative Coupling Polymerization

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Product

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Biobased Anethole-Functionalized Poly(phenylene oxides): New Low Dielectric Materials with High T_g and Good Dimensional Stability

Biobased Anethole-Functionalized Poly(phenylene oxides): New Low Dielectric Materials with High T_g and Good Dimensional Stability