A Cocatalytic Effect between Meldrum's Acid and Benzoxazine Compounds in Preparation of High Performance Thermosetting Resins

Chen, Yi; Lin, Liang-Kai; Chiang, Shu‐Jen; Liu, Ying‐Ling

doi:10.1002/marc.201600616

Cited by 16 publications

(23 citation statements)

References 23 publications

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“…The char yield of CR‐MA‐SCP is about 48 wt%, which is close to that measured with CR‐MA‐bisF. Finally, MA derivatives based thermosetting resins have shown low dielectric ( k ) constants in our previous work . The inherent low‐ k property has been attributed to the air trapped in the microcavities of the resins generated with the released CO 2 and acetone molecules in the curing process.…”

Section: Resultssupporting

confidence: 81%

“…As ketene groups generated from MA thermolysis reaction could undergo self‐cycloaddition reaction and [2+4] or [2+2] cycloaddition reaction with furan group, MA‐bisF itself could be considered as a thermally curable monomer for preparation of the corresponding thermosetting resin (Scheme ) . As the possible melting point and reaction temperature of MA‐bisF are very close to each other, MA‐bisF almost does not have a processing window (the region between melting point and reaction temperature) for molten process.…”

Section: Resultsmentioning

confidence: 99%

“…As MA‐based resins inherently have low dielectric constants, MA derivatives are potential modifiers for conventional thermosetting resins. Our previous work has demonstrated this issue with examples of MA/benzoxazine cocuring systems . The co‐catalytic effect between MA and benzoxazine groups reduces the curing temperatures and depresses the phase separation occurrence in the curing process.…”

Section: Resultsmentioning

confidence: 99%

“…As MA is an effective precursor to generate the highly reactive ketene group which could undergo self‐dimerization and addition reaction to other groups, a new class of thermosetting resins based on MA derivatives as monomers has been explored in our previous work . The MA monomers are multifunctional as they possess one MA group and styrenic/furan groups which are reactive toward ketene groups.…”

Section: Introductionmentioning

confidence: 99%

“…The MA monomers are multifunctional as they possess one MA group and styrenic/furan groups which are reactive toward ketene groups. With the contribution of the evolved acetone and CO 2 molecules in the thermally curing process, the corresponding MA‐based thermosetting resins exhibit high fractions of free volume and inherently low dielectric constants …”

Section: Introductionmentioning

confidence: 99%

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Thermosetting Resins Based on a Self-Crosslinkable Monomer/Polymer Possessing Meldrum's Acid Groups

Chou

Chen

Lin

et al. 2017

Macromol. Chem. Phys.

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Thermosetting resins based on Meldrum's acid (MA) derivatives as monomers show high thermal stability and inherent low‐dielectric constants. In this work, a multifunctional MA derivative (MA‐bisF) possessing two MA and two furan groups is newly prepared. Characterization of MA‐bisF has been carried out with Fourier transform infrared, 1H NMR, mass spectroscopy, and elemental analysis. Self‐crosslinking MA‐bisF results in the corresponding thermosetting resin mediating the addition reaction between ketene/ketene and ketene/furan groups. MA‐bisF is also utilized as a modifier for bismaleimide (BMI) resins through polymerizing MA‐bisF and BMI through Diels–Alder reaction. The corresponding crosslinked MA‐bisF/BMI resin possesses a high content of fused‐ring structure and a high crosslinking density, so as to exhibit high thermal stability (392 °C), high glass transition temperature (262 °C), high char yield (48 wt%), and a low‐dielectric constant of 2.78 at 1 MHz. A new type of reactive polymers and the corresponding high‐performance crosslinked resins has been demonstrated.

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Section: Resultssupporting

confidence: 81%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Thermosetting Resins Based on a Self-Crosslinkable Monomer/Polymer Possessing Meldrum's Acid Groups

Chou

Chen

Lin

et al. 2017

Macromol. Chem. Phys.

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Thermally stable, flame retardant, low‐dielectric constants, and flexible thermosetting resins based on a tetra‐functional benzoxazine compound possessing a cyclic siloxane core

Lee

Liu

2022

J of Applied Polymer Sci

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Cyclosiloxanes possessing organic functional moieties are reactive organic–inorganic hybrids as effective building blocks for preparation of organic–inorganic nanocomposites. In this work, a tetra‐functional benzoxazine compound (cD4‐4Bz) with a cyclosiloxane core has been synthesized, cD4‐4Bz could be considered as a self‐crosslinkable benzoxazine compound and has been utilize in preparation of the corresponding polybenzoxazine‐cyclosiloxane thermosetting resins. The obtained crosslinked polybenzoxazines exhibit good film formability and attractive thermal properties including a thermal stability above 390°C, a glass transition temperature above 400°C, and a char yield of 64.5 wt% at 800°C, and low dielectric constant of 2.74 and a dissipation factor of 0.18 at 10 GHz. The hig char yield also indicates its high flame retardancy with a calculated limited oxygen index of 44. Moreover, cD4‐4Bz is a suitable agent for polymer modification through cocuring reactions with a tetrafunctional cyclosiloxane‐phenol compound, a main‐chain benzoxazine, and a bifunctional benzoxazine compound. One prepared sample has exhibited a high thermal stability above 435°C and a char yield of 72.9 wt%. The high flexibility and variety in the fabrication of high‐performance thermosetting resin have been demonstrated.

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Toward efficient functionalization of polystyrene backbone through ketene chemistry: Synthesis, characterization, and DFT study

Heydari

Hosseini

Darroudi

et al. 2022

Polymers for Advanced Techs

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In this study, polystyrene was functionalized with Meldrum's acid toward the introduction of the ketenes (C C O) system to its backbone for producing a dramatically reactive intermediate. Meldrum's acid, as a ketene source, was reacted by poly(styrene-co-p-chloromethyl styrene) through a simple nucleophilic reaction to synthesize poly(styrene-co-styryl Meldrum's acid). Then, the pendant Meldrum's acid under thermal treatment converted to ketene intermediate resulting in highly reactive polystyrenes derivatives, which rapidly reacted by nucleophilic reagents to afford ultimate organic building blocks. The polystyrene derivatives were characterized using elemental analysis, FT-IR, high-resolution solid-state NMR, thermogravimetric analysis (TGA), and differential thermogravimetric analysis (DTG). To clarify the evolutionary mechanisms of polystyrene products, density functional theory (DFT) method B3LYP with the 6-311++G(2d,p) basis set was used. We studied the preparation of polystyrene model compounds through Meldrum's acid thermolysis and nucleophilic substitution. The kinetic and thermodynamic parameters in all reactions and the structural and electronic properties of all molecules were calculated. These data exhibited that based on Gibbs Free energy values, the structure of syndiotactic polystyrene is more stable than that of isotactic polystyrene. Furthermore, it was found that the presence of an electron donor or acceptor substituent on the polystyrene structure affects the electronic bandgap.

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A Cocatalytic Effect between Meldrum's Acid and Benzoxazine Compounds in Preparation of High Performance Thermosetting Resins

Cited by 16 publications

References 23 publications

Thermosetting Resins Based on a Self-Crosslinkable Monomer/Polymer Possessing Meldrum's Acid Groups

Thermosetting Resins Based on a Self-Crosslinkable Monomer/Polymer Possessing Meldrum's Acid Groups

Thermally stable, flame retardant, low‐dielectric constants, and flexible thermosetting resins based on a tetra‐functional benzoxazine compound possessing a cyclic siloxane core

Toward efficient functionalization of polystyrene backbone through ketene chemistry: Synthesis, characterization, and DFT study

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