Molecular origin of unusual physical and mechanical properties in novel phenolic materials based on benzoxazine chemistry

Wirasate, Supa; Dhumrongvaraporn, Sujitra; Allen, Douglas J.; Ishida, Hatsuo

doi:10.1002/(sici)1097-4628(19981114)70:7<1299::aid-app6>3.0.co;2-h

Cited by 124 publications

(97 citation statements)

References 10 publications

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“…Polybenzoxazines exhibit unique properties like nearly zero shrinkage upon curing, good thermal stability, good chemical resistance, low water absorption and wide processing window [7][8][9][10][11] . Though the dielectric constants of polybenzoxazines are low, it needs to be reduced further to find better utility in microelectronics applications.…”

Section: Introductionmentioning

confidence: 99%

Development of a polybenzoxazine/TSBA-15 composite from the renewable resource cardanol for low-k applications

et al. 2015

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The present work describes the synthesis of a novel cardanol based benzoxazine monomer (CBz) from renewable resource of cardanol using caprolactamdiamine (CPLDA) by a solventless method. Thiol functionalized mesoporous silica (TSBA-15) was incorporated into cardanol based benzoxazine matrix (PCBz) and the structure of TSBA-15/PCBz was confirmed by FT-IR and NMR analysis. Surface morphology of TSBA-15/PCBz was determined by SEM and TEM techniques. From the TEM results, it was observed that the dispersion of thiol functionalized mesoporous silica in to PCBz forms a fibrous material, which imparts free volume. Thermal properties were studied by DSC and TGA analysis. From the results, it was noticed that the enhanced thermal properties were observed with varying the weight percentage of TSBA-15 material. Dielectric data obtained from impedance analyzer shows that the TSBA-15/PCBz composites have lower values of dielectric constant, and dielectric loss. These above results conclude that TSBA-15/PCBz composites obtained from a renewable waste cardanol finds application as electrical resistance material in microelectronic applications.

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Section: Introductionmentioning

confidence: 99%

Development of a polybenzoxazine/TSBA-15 composite from the renewable resource cardanol for low-k applications

et al. 2015

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“…It may be assumed that H-bonds present in the epoxy-benzoxazine blend prevented orientation and arrangement of polyether chains into crystal structure. Intermolecular bonds in the epoxy-benzoxazine system have been demonstrated and studied by several authors [4,15,33,34]. Therefore, from results obtained by DSC measurements it may be concluded that benzoxazine surfactant should be homogeneously incorporated in epoxy matrix and that secondary interactions between epoxy and benzoxazine compounds were established.…”

Section: Curing Behavior Of Epoxy-benzoxazine Filmsmentioning

confidence: 93%

Novel epoxy-benzoxazine water-based emulsions with reactive benzoxazine surfactants for coatings

Ambrožič¹,

Šebenik²,

Krajnc

2014

Express Polym. Lett.

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Abstract. Novel epoxy-benzoxazine emulsions designed for water-based coatings were prepared and investigated. Bisphenol#A-based epoxy resins with molar weights of 340, 377 and 1750 g/mol along with epoxidized soybean oil were emulsified using mono-and bi-functional benzoxazine surfactants, which are able to react with epoxy resins at their cure temperature. The structure of synthesized surfactants carrying one or two polyether chains was confirmed using Fourier transform infrared spectroscopy, 1 H nuclear magnetic resonance and differential scanning calorimetry. Stability of emulsions was verified by particle diameters measurements. Coatings, made directly from emulsions, were dried and cured at elevated temperature using 3,3$-dimetoxybenzidine as curing agent to ensure a highly cross-linked structure of thermosetting films. Curing process, thermal properties and hardness of cured films were investigated. It was found that benzoxazine molecules were well incorporated into the epoxy network upon curing, which ensures no void structure of cured copolymer and enhanced coating properties.

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“…3 The intermolecular hydrogen-bonding interactions could be significantly reduced at the elevated temperature (viz. 3 The intermolecular hydrogen-bonding interactions could be significantly reduced at the elevated temperature (viz.…”

Section: Hydrogen-bonding Interactionsmentioning

confidence: 99%

“…[1][2][3][4][5] Different with other thermosetting (TS) resins such as epoxy, cyanate ester, and bismaleimide resins, PBZ has a lot of intramolecular or intermolecular hydrogen bonds (H-bonds) [Scheme 1(a, b)], 6 which endow PBZ with amazing properties, such as high glass transition temperature (T g ), high modulus, and low moisture absorption. [1][2][3][4][5] Different with other thermosetting (TS) resins such as epoxy, cyanate ester, and bismaleimide resins, PBZ has a lot of intramolecular or intermolecular hydrogen bonds (H-bonds) [Scheme 1(a, b)], 6 which endow PBZ with amazing properties, such as high glass transition temperature (T g ), high modulus, and low moisture absorption.…”

Section: Introductionmentioning

confidence: 99%

Poly(ether imide)‐modified benzoxazine blends: Influences of phase separation and hydrogen bonding interactions on the curing reaction

Zhao

Liang

Chen

et al. 2012

J of Applied Polymer Sci

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Polymer blends of polybenzoxazine (PBZ)/poly(ether imide) (PEI) were prepared by the in situ curing reaction of benzoxazine (BZ) resin in the presence of PEI. Phase separation induced by the polymerization of BZ resin was observed. The rheological behaviors, morphologies, and their evolution process of BZ/PEI blends were investigated by rheometer and scanning electron microscope. Phase separation that took place at the early stage of the curing reaction effectively reduced the dilution effect of PEI. Fourier transform infrared (FTIR) results suggested that hydrogen bonds between PBZ and PEI existed during the whole curing process, although weakened with phase separation. The decrease of isoconversion activation energy indicated that the polymerization of BZ resin was facilitated in the presence of such kind of hydrogen-bonding interactions. By changing the weight fraction of PEI, extensive phase separation was obtained in PBZ blends with 5 and 20 wt % of PEI, in which systems, the crosslinking density and glass transition temperature (T g ) of PBZ-rich phase were greatly improved compared to this single PBZ system. Scheme 1 . H-bonds that could possibly occur in the blends of PEI and PBZ: (a) intramolecular H-bonds between hydroxyl group and nitrogen atom on the Mannich bridge via six-membered ring, (b) intermolecular H-bonds between hydroxyl group and hydroxyl group or hydroxyl group and nitrogen atom on the Mannich bridge, and (c) intermolecular Hbonds between the carbonyl group of PEI and hydroxyl group of PBZ. Scheme 2. Chemical structures of B-BZ and PEI.ARTICLE 2866

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Molecular origin of unusual physical and mechanical properties in novel phenolic materials based on benzoxazine chemistry

Cited by 124 publications

References 10 publications

Development of a polybenzoxazine/TSBA-15 composite from the renewable resource cardanol for low-k applications

Development of a polybenzoxazine/TSBA-15 composite from the renewable resource cardanol for low-k applications

Novel epoxy-benzoxazine water-based emulsions with reactive benzoxazine surfactants for coatings

Poly(ether imide)‐modified benzoxazine blends: Influences of phase separation and hydrogen bonding interactions on the curing reaction

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