Synthesis of epoxy‐functionalized hyperbranched poly(phenylene oxide) and its modification of cyanate ester resin

Huang, Pingzhen; Gu, Aijuan; Liang, Guozheng; Yuan, Li

doi:10.1002/app.34791

Cited by 19 publications

(20 citation statements)

References 26 publications

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“…[10][11][12][13][14][15][16][17] As outlined by Guenthner et.al, the key properties for identifying 'improved' polycyanurate system include (1) ease of processing, (2) high T g , (3) excellent mechanical properties such as elastic modulus and impact strength, (4) low moisture absorption and (5) low dielectric constant. 18 Considering these guidelines, we were interested in developing CE monomers that would result in the formation of polycyanurates with lower moisture absorption and better processibility.…”

Section: Introductionmentioning

confidence: 99%

Cyanate ester resins containing pentadecyl-substituted cyclohexyl moiety: Synthesis, curing and structure–property relationship

Kulkarni

Tawade

Wadgaonkar

2012

High Performance Polymers

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Cyanate ester (CE) monomers containing pentadecyl-substituted cyclohexyl moieties such as 1,1-bis(4-cyanatophenyl) 3-pentadecylcyclohexane and 1,1-bis(4-cyanatophenyl) cyclohexane were synthesized and characterized by Fourier transform infrared, proton-nuclear magnetic resonance ( 1 H-NMR) and carbon-nuclear magnetic resonance ( 13 C-NMR) spectroscopies as well as differential scanning calorimetry (DSC). Both 1,1-bis(4-cyanatophenyl) 3-pentadecylcyclohexane and 1,1-bis(4-cyanatophenyl) cyclohexane exhibited better processability coupled with lower melting points, lower cure onset with broad cure exotherm than the commercially available CE monomer, namely, 2,2-bis(4-cyanatophenyl) propane. Glass transition temperatures of cured 2,2-bis(4-cyanatophenyl) propane, 1,1-bis(4-cyanatophenyl) cyclohexane and 1,1-bis(4-cyanatophenyl) 3-pentadecylcyclohexane were observed to be 288 C, 302 C and 160 C, respectively. Cured 1,1-bis(4-cyanatophenyl) cyclohexane displayed higher storage modulus (1.59 Â 10 9 Pa) than 1,1-bis(4-cyanatophenyl) 3-pentadecylcyclohexane (1.07 Â 10 9 Pa) and 2,2-bis(4-cyanatophenyl) propane (1.39 Â 10 9 Pa). The order of thermal stability of cured polycyanurates was found to be 2,2-bis(4-cyanatophenyl) propane > 1,1-bis(4-cyanatophenyl)cyclohexane > 1,1-bis(4-cyanato phenyl) 3-pentadecylcyclohexane. The moisture absorption of cured resins derived from 1,1-bis(4-cyanatophenyl) 3-pentadecyl cyclohexane and 1,1-bis(4-cynatophenyl)cyclohexane was found to be lower than that of 2,2-bis(4-cynatophenyl) propane implying the role of pentadecyl substituent and/or cyclohexyl moiety in imparting hydrophobicity to the polycyanurates.

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Section: Introductionmentioning

confidence: 99%

Cyanate ester resins containing pentadecyl-substituted cyclohexyl moiety: Synthesis, curing and structure–property relationship

Kulkarni

Tawade

Wadgaonkar

2012

High Performance Polymers

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“…The fact that all the cyanate groups are not consumed in this temperature regime, suggests that this reaction occurs only in part. It is also possible that the cyclotrimerization of cyanate groups can be further triggered by the OH groups, as proved by the previous reports [21–23]. The modification of cyanate ester resin by hydroxyl-terminated liquid butadiene acrylonitrile rubber has been reported which also shows the existence of an addition reaction between hydroxyl groups and cyanate groups [24].…”

Section: Resultsmentioning

confidence: 70%

Tuning the mechanical properties of glass fiber-reinforced bismaleimide–triazine resin composites by constructing a flexible bridge at the interface

Zeng¹,

Yu²,

Lai³

et al. 2013

Science and Technology of Advanced Materials

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We demonstrate a new method that can simultaneously improve the strength and toughness of the glass fiber-reinforced bismaleimide–triazine (BT) resin composites by using polyethylene glycol (PEG) to construct a flexible bridge at the interface. The mechanical properties, including the elongation, ultimate tensile stress, Young’s modulus, toughness and dynamical mechanical properties were studied as a function of the length of PEG molecular chain. It was found that the PEG molecule acts as a bridge to link BT resin and glass fiber through covalent and non-covalent bondings, respectively, resulting in improved interfacial bonding. The incorporation of PEG produces an increase in elongation, ultimate tensile stress and toughness. The Young’s modulus and Tg were slightly reduced when the length of the PEG molecular chain was high. The elongation of the PEG-modified glass fiber-reinforced composites containing 5 wt% PEG-8000 increased by 67.1%, the ultimate tensile stress by 17.9% and the toughness by 78.2% compared to the unmodified one. This approach provides an efficient way to develop substrate material with improved strength and toughness for integrated circuit packaging applications.

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“…Figure 5 shows the tan ∂-temperature plots for cured CE, p-CE, and CE/eHBPPO resins. [266] A. Ghosh et al…”

Section: Hyperbranched Phenylene Oxide As a Low Temperature Curing Agentmentioning

confidence: 96%

“…An epoxy-functionalized hb-PPO (epoxy-hb-PPO) (see structure in Scheme 29) was synthesized by Huang et al [266] and the effect of adding 2.5-15% of epoxyhb-PPO on the curing mechanism and kinetics of cyanate ester (CE) was studied. Each prepolymer showed one exothermic peak; however, interestingly, all peaks of CE/epoxy-hb-PPO prepolymers appeared at a significantly lower temperature than those of CE prepolymer, demonstrating that an additional reaction took place in the CE/epoxy-hb-PPO resin system.…”

Section: Hyperbranched Phenylene Oxide As a Low Temperature Curing Agentmentioning

confidence: 99%

Aromatic Hyperbranched Polymers: Synthesis and Application

Ghosh

Banerjee

Voit

2014

Porous Carbons – Hyperbranched Polymers – Polymer Solvation

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Hyperbranched (hb) polymers have been receiving increasing attention because of their unique architecture that results in an interesting set of unusual chemical and physical properties. Over the past decade quite a number of excellent reviews on hb polymers have been published by different research groups, covering various aspects of this class of polymers. This review will highlight the work on aromatic hb polymers of the last decade, emphasizing general synthetic strategies and recent development of alternative synthetic strategies, and discussing various aspects of hb polymers to demonstrate their wide range of applications.

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Synthesis of epoxy‐functionalized hyperbranched poly(phenylene oxide) and its modification of cyanate ester resin

Cited by 19 publications

References 26 publications

Cyanate ester resins containing pentadecyl-substituted cyclohexyl moiety: Synthesis, curing and structure–property relationship

Cyanate ester resins containing pentadecyl-substituted cyclohexyl moiety: Synthesis, curing and structure–property relationship

Tuning the mechanical properties of glass fiber-reinforced bismaleimide–triazine resin composites by constructing a flexible bridge at the interface

Aromatic Hyperbranched Polymers: Synthesis and Application

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