Synthesis, curing behavior, and thermal properties of fluorene-based benzoxazine-endcapped copoly(ether ketone ketone)s

Wang, Hui; Wang, Jun; Feng, Tiantian; Ramdani, Noureddine; Li, Yue; Xu, Xiaodong; Liu, Wenbin

doi:10.1007/s10973-014-4294-1

Cited by 11 publications

(9 citation statements)

References 52 publications

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“…Thermosetting resins, such as phenolic resins, epoxides, bismaleimides, cyanates, vinyl esters, and polyimides, are high-performance polymers with a wide range of applications in aerospace, structural, adhesives, electronics, and coatings fields. In recent years, polybenzoxazine resins have gained immense attention in academia and industry, because they combine the thermal and mechanical strength of phenolic resins with much wider molecular design flexibility and overcome several disadvantages of traditional phenolic resins [1,2,3,4,5,6,7,8,9,10,11,12]. These resins have a number of excellent properties such as high carbon yield, low water absorption, high mechanical strength, high glass transition temperature ( T g ), very low shrinkage, and no byproduct formation during the curing process.…”

Section: Introductionmentioning

confidence: 99%

“…These resins have a number of excellent properties such as high carbon yield, low water absorption, high mechanical strength, high glass transition temperature ( T g ), very low shrinkage, and no byproduct formation during the curing process. However, polybenzoxazine still has shortcomings such as being cured at higher temperature, processing difficulty, and higher brittleness [7,8,9,13]. Commonly two methodologies are employed to overcome these limitations, (i) altering the benzoxazine monomer structure by molecular design, as new functionalities can be introduced by modifying the structure of the main chain [14,15,16,17], side chain [18,19,20], or end chain structure [21,22,23,24], (ii) by adding a second component such as nano-inorganic particles [25,26,27,28], rubber elastomers [29], fiber [30], or thermoplastic polymers [31,32,33].…”

Section: Introductionmentioning

confidence: 99%

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Amino-Functionalized Lead Phthalocyanine-Modified Benzoxazine Resin: Curing Kinetics, Thermal, and Mechanical Properties

Gao

Pan

et al. 2019

Polymers

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Phenol-diaminodiphenylmethane-based benzoxazine (P-ddm)/phthalocyanine copolymer was prepared by using P-ddm resin as matrix and 3,10,17,24-tetra-aminoethoxy lead phthalocyanine (APbPc) as additive. Fourier-transform infrared (FTIR), differential scanning calorimetry (DSC), dynamic mechanical analysis (DMA), and thermogravimetric analysis (TGA) were used to investigate the curing behavior, curing kinetics, dynamic mechanical properties, thermal stability, and impact strength of the prepared copolymers. The kinetic parameters for the P-ddm/APbPc blend curing processes were examined by utilizing the iso-conversional, Flynn–Wall–Ozawa, and Málek methods. The P-ddm/APbPc blends exhibit two typical curing processes, and DSC results confirmed that the blending of APbPc monomer can effectively reduce the curing temperature of P-ddm resin. The autocatalytic models also described the non-isothermal curing reaction rate well, and the appropriate kinetic parameters of the curing process were obtained. The DMA and impact strength experiments proved that the blending of APbPc monomer can significantly improve the toughness and stiffness of P-ddm resin, the highest enhancements were observed on 25 wt.% addition of APbPc, the recorded values for the storage modulus and impact strength were 1003 MPa and 3.60 kJ/m2 higher, respectively, while a decline of 24.6 °C was observed in the glass transition temperature values. TGA curves indicated that the cured copolymers also exhibit excellent thermal stabilities.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Amino-Functionalized Lead Phthalocyanine-Modified Benzoxazine Resin: Curing Kinetics, Thermal, and Mechanical Properties

Gao

Pan

et al. 2019

Polymers

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“…This group also synthesized a series of fluorene‐based benzoxazine‐endcapped copoly(ether ketone ketone)s (co‐PEKKs). The results indicate that the incorporation of co‐PEKKs within the benzoxazine backbone considerably improves the toughness of the fluorene‐containing polybenzoxazines without much sacrifice of their thermal properties …”

Section: Introductionmentioning

confidence: 97%

Copolymerization of fluorene‐based main‐chain benzoxazine and their high performance thermosets

Feng

Wang

et al. 2015

Polymers for Advanced Techs

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A series of fluorene-based benzoxazine copolymers were synthesized from the mixture of 9,9-bis(4-hydroxyphenyl) fluorene and bisphenol A, and 4,4′-diaminodiphenyloxide and paraformaldehyde. And the cured polybenzoxazine films derived from these copolymers were also obtained. Fourier transform infrared spectroscopy (FTIR) and hydrogen nuclear magnetic resonances confirmed the structure of these benzoxazines. Their molecular weight was estimated by gel permeation chromatography. The curing behavior of the precursors was monitored by FTIR and differential scanning calorimetry. Dynamic mechanical analysis and thermogravimetric analysis were performed to study the thermal properties of the cured polymers. The cured polybenzoxazines exhibit excellent heat resistance with glass transition temperatures (T g ) of 286-317°C, good thermal stability along with the values of 5% weight loss temperatures (T 5 ) over 340°C, and high char yield over 50% at 800°C. The mechanical properties of the cured polymers were also measured by bending tests.

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“…10,[17][18][19] Polymers containing fluorene moieties, for example, epoxies, polybenzoxazines, polyamides, and polyimides, exhibit many attractive properties. [20][21][22][23][24] Our laboratory group successfully synthesized a novel amino-containing fluorene-based bisphthalonitrile (AFPN) monomer, which can be cured in the absence of curing agents. The synthesized resin exhibited an enhanced thermal/thermooxidative stability.…”

Section: Introductionmentioning

confidence: 99%

Novel amino-containing fluorene-based bisphthalonitrile compounds with flexible group

Wang

Dayo

et al. 2017

High Performance Polymers

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A series of amino-containing fluorene-based bisphthalonitrile (AFPN) monomers with alkyl or alkoxy groups were successfully produced by the reaction of 4-nitrophthalonitrile with 9, 9-bis (3-alkyl (or alkoxy)-4-aminophenyl)-2, 7-dihydroxylfluorene in the presence of potassium carbonate by a nucleophilic substitution reaction. The chemical structures of the synthesized monomers were confirmed by the Fourier transform infrared (FTIR), proton nuclear magnetic resonance, and carbon-13 nuclear magnetic resonance analyses. The synthesized monomers’ curing behaviors were evaluated by FTIR and differential scanning calorimetry, and a rheological analysis was performed to evaluate their respective processabilities. Moreover, dynamic mechanical analysis (DMA) and thermogravimetric analysis (TGA) were performed for the thermomechanical, thermal, and thermo-oxidative analyses of the polymers. The results confirmed that the newly prepared phthalonitrile (PN) monomers with alkyl or alkoxy groups exhibited a self-promoted curing behavior. The rheological analysis suggested that the processing windows of the synthesized monomers were wider than that of APFN monomer bearing no flexible group. DMA and TGA revealed that the cured polymers exhibited high glass transition temperature (358–416°C) and the char yields at 800°C under nitrogen were between 70% and 77%. Moreover, the introduction of alkyl or alkoxy groups into the PN monomers’ backbones slightly reduced the thermal stability of the resulting polymers.

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Synthesis, curing behavior, and thermal properties of fluorene-based benzoxazine-endcapped copoly(ether ketone ketone)s

Cited by 11 publications

References 52 publications

Amino-Functionalized Lead Phthalocyanine-Modified Benzoxazine Resin: Curing Kinetics, Thermal, and Mechanical Properties

Amino-Functionalized Lead Phthalocyanine-Modified Benzoxazine Resin: Curing Kinetics, Thermal, and Mechanical Properties

Copolymerization of fluorene‐based main‐chain benzoxazine and their high performance thermosets

Novel amino-containing fluorene-based bisphthalonitrile compounds with flexible group

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