Fluorinated low molecular weight poly(phenylene oxide): Synthesis, characterization, and application in epoxy resin toward improved thermal and dielectric properties

Zhou, Yubin; Peng, Zhongquan; Ji, Jingqi; Wu, Yanran; Chen, Zhigeng; Huang, Haohao; Liu, Shumei; Zhao, Jianqing

doi:10.1016/j.eurpolymj.2021.110674

Cited by 29 publications

(17 citation statements)

References 38 publications

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“…BCB-DA-10 had the lowest polarization, which was consistent with the changing trend of the dielectric constant. In addition, the modified epoxy resin was compared with commercial dielectric materials and the reported low- k epoxy thermosets. ,,,− ,− As shown in Figure d, the k value of the modified epoxy resin is relatively low compared with the low- k materials (Tables S2 and S3).…”

Section: Resultsmentioning

confidence: 99%

“…Yield: 85%. 1 H NMR (500 MHz, DMSO) δ 7.08 (d, J = 7.5 Hz, 1H), 7.01 (dd, J = 7.6, 1.0 Hz, 1H), 6.99 (s, 1H), 6.92 (s, 1H), 6.90 (s, 1H), 3.15 (s, 4H). 13 C NMR (126 MHz, DMSO) δ: 179.9 (s), 146.8 (s), 145.4 (s), 143.9 (s), 143.0 (s), 141.1 (s), 139.5 (s), 134.0 (s), 128.2 (s), 125.9 (s), 125.8 (s), 123.7 (s), 122.5 (s), 46.8 (s), 45 Preparation of Modified Epoxy Resins with BCB-DA.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

“…Epoxy resins are widely used in printed circuit boards (PCBs) in modern communications and electronics, owing to their excellent insulation, adhesion, and thermal resistance properties. − With the development of high-frequency communication, the miniaturization of integrated circuit (IC) components has led to interconnected signal delays and losses that are proportionally correlated with the dielectric constant ( k ) of the insulating material. − Therefore, matrix resins used as insulation and bracing in the manufacturing of PCBs should have a lower dielectric constant, reduced water absorption, and higher adhesion. , In the current scenario, traditional epoxy resins fail to meet the lower dielectric requirements of modern PCB substrates because they generate hydroxyl, imine, ester, and other highly polar groups after curing. , These polar groups enhance the hygroscopicity of epoxy resins, causing further deterioration of their dielectric properties. , In this context, the development of low- k epoxy resins with outstanding comprehensive properties has gained considerable interest as a research topic.…”

Section: Introductionmentioning

confidence: 99%

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Preparation of Hydrophobic Low-k Epoxy Resins with High Adhesion Using a Benzocyclobutene-Rosin Modifier

Zhou

Shen

et al. 2023

ACS Sustainable Chem. Eng.

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With the development of high-frequency communication, the miniaturization of integrated circuits (ICs) has led to interconnected signal delays and losses. The dielectric properties of epoxy resins are no longer satisfactory, because of the presence of polar groups. Herein, a benzocyclobutene-rosin modifier was designed and synthesized to reduce the dielectric constant of epoxy resins. The recross-linking network of benzocyclobutene inhibits the polarizability of the polar groups, and rosin skeletons increase the free volume of epoxy resins. Consequently, the dielectric constant of epoxy resins decreased from 3.12 to 2.72 and their water absorption decreased from 1.06% to 0.861%. The dielectric constant and water absorption are lower than those of most commercial dielectric materials. Additionally, the adhesion of epoxy resins was improved, which broke the contradiction between the dielectric properties and the adhesion of traditional epoxy resins. The modified epoxy resin was finally applied to printed circuit boards. At 15 GHz, its signal loss was 28.8 dB, which was lower than that of a commercial epoxy resin (FR-4), demonstrating that the modified epoxy resin can better meet the miniaturization needs of ICs.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Materials and Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Preparation of Hydrophobic Low-k Epoxy Resins with High Adhesion Using a Benzocyclobutene-Rosin Modifier

Zhou

Shen

et al. 2023

ACS Sustainable Chem. Eng.

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“…For such applications, the properties of POZs in the solid state such as T g , crystallinity, and thermal degradation are of great importance. Low molecular weight polymers are being widely investigated for their potential applications in additive manufacturing, injection molding, and plasticizing. , Moreover, these polymers can be used as compatibilizers to enhance the processability of materials . Rubberlike materials such as polymers that exhibit a T g below their utilization temperature are used in a variety of fields including adhesives, compatibilizers, plasticizers, fillers, etc .…”

Section: Introductionmentioning

confidence: 99%

“… 33 , 34 Moreover, these polymers can be used as compatibilizers to enhance the processability of materials. 35 Rubberlike materials such as polymers that exhibit a T g below their utilization temperature are used in a variety of fields including adhesives, compatibilizers, plasticizers, fillers, etc. 36 On the other hand, crystallinity of a polymer contributes to its application in other fields such as encapsulation, entrapment, and thermoresponsive release of desired substances.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Structure–Property Relationship of Amphiphilic Poly(2-ethyl-co-2-(alkyl/aryl)-2-oxazoline) Copolymers

et al. 2022

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Poly(2-oxazoline)s (POZs) are widely investigated for their applications in various fields due to their unique properties. To exploit and combine different characteristics of the POZ family, 2-oxazoline monomers can be copolymerized to prepare tailor-made copolymers with the desired glass transition temperature (T g), melting temperature (T m), amphiphilicity, and functionality. Here, we report the synthesis and characterization of 2-oxazoline monomers and a range of POZ copolymers produced, thereof. 2-Propyl-2-oxazoline (PrOZ) and 2-pentyl-2-oxazoline (PeOZ) monomers were synthesized by two different methods starting from nitriles or carboxylic acids. A number of POZ copolymers were synthesized by copolymerization of 2-ethyl-2-oxazoline (EOZ) with either one of PrOZ, PeOZ, or 2-phenyl-2-oxazoline (PhOZ) at three different compositions (25:75, 50:50, and 75:25) and three molecular weights (1000, 2000, and 5000 Da). The successful synthesis of the monomers and copolymers was demonstrated through their structural analysis by 1H NMR and FTIR. SEC results confirmed the targeted molar masses of the copolymers and living nature of the polymerization by showing low dispersity values. Thermal properties of the copolymers were studied using DSC and TGA. DSC studies revealed the amorph and random state of the copolymers with obtained T g values for the copolymers in the range of −3 to 84 °C depending on their molecular weight and type of the side chain. While the presence of longer aliphatic side chains resulted in lower T g values, the presence of 2-phenyl substituents on the polymer led to higher T g values. The decomposition temperatures determined by TGA were in the range of 328 to 383 °C depending on the molecular weight, composition, and side chain of the copolymers. It was observed that higher molecular weights led to higher T g values and decomposition temperatures. While copolymers with aliphatic side chains exhibited a single-step decomposition profile, the decomposition of copolymers having aromatic side chains occurred in multiple steps. The variations in the molecular weight, composition, and side chains of the copolymers resulted in a library of tailorable amphiphilic copolymers suitable for multiple applications ranging from biomedical applications to composite manufacturing.

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Preparation and characterization of high temperature resistant thermosetting polyphenylene ether resin

et al. 2022

J of Applied Polymer Sci

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To explore high thermal properties, low dielectric constant and loss for copper clad laminates, poly(phenylene oxide) (PPE) with different end groups (allyl and epoxide groups) were successfully prepared. Firstly, low molecular weight polyphenylene ether was synthesized using the redistribution method. Then the polyphenylene ether thermosetting polymers by modifying their terminal hydroxyl groups were reported and their fundamental materials properties were compared. Through property tests and data analyses, it was found that PPE with vinyl end groups had the best performances, especially high glass transition temperature (about 230°C), the thermal conductivity was 0.32–0.38 Wm−1 K−1, low dielectric constant (about 2.5) and low dielectric loss (about 4.4 × 10−3). The possible reason was that the main chain of polyphenylene ether contains non‐polar crosslinkable group (CC). In a word, through properties comparison of thermosets of PPE, the results demonstrated that the materials of all systems were suitable for using as printed circuit boards.

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Fluorinated low molecular weight poly(phenylene oxide): Synthesis, characterization, and application in epoxy resin toward improved thermal and dielectric properties

Cited by 29 publications

References 38 publications

Preparation of Hydrophobic Low-k Epoxy Resins with High Adhesion Using a Benzocyclobutene-Rosin Modifier

Preparation of Hydrophobic Low-k Epoxy Resins with High Adhesion Using a Benzocyclobutene-Rosin Modifier

Synthesis and Structure–Property Relationship of Amphiphilic Poly(2-ethyl-co-2-(alkyl/aryl)-2-oxazoline) Copolymers

Preparation and characterization of high temperature resistant thermosetting polyphenylene ether resin

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