Design of acetylene-modified bio-based tri-functional benzoxazine and its copolymerization with bismaleimide for performance enhancement

Xing, Yunliang; Zhang, Yuan; He, Xianru

doi:10.1007/s00289-022-04639-8

Cited by 4 publications

(2 citation statements)

References 46 publications

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“…Generally, the cured benzoxazine resin from a benzoxazine monomer with more oxazine rings (functional groups) tends to have high heat-resistance − ; however, reported tri- or multifunctional benzoxazine monomers (SCI database) were not synthesized through green strategy. To the best of our knowledge, about 30 GreenBenz resins were reported (SCI database), − but only one of them has a glass transition temperature ( T g ) higher than 300 °C; moreover, the static mechanical properties of only four GreenBenz resins were reported. ,, Therefore, it is a meaningful project to develop a new high-performance biobased benzoxazine resin by synthesizing a unique trifunctional GreenBenz.…”

Section: Introductionmentioning

confidence: 99%

Preparation of Thermally Resistant and Mechanically Strong Biomass Benzoxazine Resins via Green Strategy

Liu,

Yuan,

Liang

et al. 2024

ACS Sustainable Chem. Eng.

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Developing biomass resins with high thermal resistance and mechanical performance through a green strategy is an interesting challenge. Increasing the functionality of oxazine ring is favorable to improve the thermal resistance and mechanical strength of resins; however, no tri-or more functional benzoxazine monomers synthesized using the green strategy have been reported. Herein, two novel trifunctional benzoxazine monomers (coded as DPTA-f and DPTR-f) with very low melting points (61, 49 °C) were synthesized using biomass raw materials (diphenolic acid, tyramine, tyrosol, and furfurylamine) and green solvents (ethanol and water). The cured resins of DPTA-f and DPTR-f, designed as P(DPTA-f) and P(DPTR-f), not only exhibit high storage moduli (3600 and 3080 MPa) and high tensile strength (65.0 and 55.1 MPa) but also have high glass transition temperature (T g = 328, 302 °C) and initial degradation temperature (351 and 350 °C), especially P(DPTA-f) exhibits bigger T g than all benzoxazine resins prepared using the green strategy (SCI database). They also have good flame retardancy. The above excellent processing nature of DPTA-f and DPTR-f together with competitive thermal resistance and mechanical strength of two cured resins benefits from the unique chemical and aggregate state structures of the biobased benzoxazines.

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Section: Introductionmentioning

confidence: 99%

Preparation of Thermally Resistant and Mechanically Strong Biomass Benzoxazine Resins via Green Strategy

Liu,

Yuan,

Liang

et al. 2024

ACS Sustainable Chem. Eng.

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“…16 Compared with traditional monofunctional and bifunctional polybenzoxazines, multifunctional polybenzoxazines usually exhibit higher mechanical property and thermal stability [17][18][19] due to the dense cross-linking networks. Xing et al 20 used resveratrol, propargylamine and paraformaldehyde to prepare a bio-based trifunctional polybenzoxazine with high thermal properties. Hyperbranched polybenzoxazines with highly cross-linking structures can be obtained by using polyphenols and polyamines as raw materials.…”

Section: Introductionmentioning

confidence: 99%

Preparation of high‐performance hyperbranched polybenzoxazine with low dielectric constant

Lin

et al. 2023

Journal of Polymer Science

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A high‐performance hyperbranched polybenzoxazine with low dielectric constant was prepared. A hyperbranched benzoxazine (HTTr‐d) was synthesized from 1,1,1‐tris(4‐hydroxyphenyl) ethane, 1,12‐dodecanediamine and paraformaldehyde through an A2 + B3 approach with p‐tertbutyl phenol as an end‐capping reagent. After thermal curing, hyperbranched polybenzoxazine (PHTTr‐d) was obtained. For comparison, trifunctional polybenzoxazine (PTr‐s) with long alkyl groups was also synthesized. The introduction of long alkyl chains can effectively reduce the dielectric constants of polybenzoxazines. Due to the presence of tertiary butyl groups and the forming of hyperbranched structure, the dielectric constant of PHTTr‐d was 2.59 at 1 MHz, which was lower than 2.68 of PTr‐s. Compared with PTr‐s, PHTTr‐d exhibited higher thermal stability with the glass transition temperature (Tg) of 197 °C. These results indicated that the hyperbranched polybenzoxazine has potential application as a low dielectric constant material in the field of electronic information.

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Design and Construction of Furan‐Based and Thiophene‐Based Salicyladazine Bisbenzoxazine Resins with High Thermal Stability and Tunable Surface Properties

Kao,

Mohamed,

Chiang

et al. 2024

Macro Chemistry & Physics

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We synthesized two disubstituted bisbenzoxazine monomers using furan (Fa) and thiophene (Th) derivatives: bis((3‐(furan‐2‐ylmethyl)‐7‐ol‐3,4‐dihydro‐2H‐benzo[e][1,3] oxazin‐6‐yl)methylene)hydrazine (BAZ‐Fa‐BZ) and bis((3‐(thiophen‐2‐ylmethyl)‐7‐ol‐3,4‐dihydro‐2H‐benzo[e][1,3] oxazin‐6‐yl)methylene)hydrazine (BAZ‐Th‐BZ). These monomers were synthesized via Mannich condensation of salicylaldazine (BAZ‐4OH) and paraformaldehyde (CH2O) with furfurylamine (Fa‐NH2) and thiophene‐2‐methenamine (Th‐NH2), respectively. The chemical structures of BAZ‐Fa‐BZ and BAZ‐Th‐BZ were affirmed using FT‐IR and NMR; respectively. A thorough investigation of the thermal polymerization process of BAZ‐Fa‐BZ and BAZ‐Th‐BZ was conducted using DSC, TGA, and in situ FT‐IR spectra (ranging from 25 to 250 °C). Poly(BAZ‐Fa‐BZ) exhibited superior thermal properties with a thermal decomposition temperature (Td10) of 402 °C and a char yield of 58 wt.% after thermal treatment at 250 °C, along with a lower surface free energy of 28.9 mJ m−2 compared to poly(BAZ‐Th‐BZ) (Td10 = 359 °C, char yield = 48 wt.%, and surface free energy = 34.1 mJ m−2). Additionally, poly(BAZ‐Th‐BZ/BAZ‐Fa‐BZ) blend with a ratio of 1/3 after thermal curing at 250 °C demonstrated the highest Td10 of 395 °C and a char yield of 60 wt.%. Photoluminescence (PL) measurements conducted in the solid state revealed that BAZ‐Th‐BZ, BAZ‐Fa‐BZ, and their blends emit green light when excited at a wavelength of 365 nm.This article is protected by copyright. All rights reserved

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Design of acetylene-modified bio-based tri-functional benzoxazine and its copolymerization with bismaleimide for performance enhancement

Cited by 4 publications

References 46 publications

Preparation of Thermally Resistant and Mechanically Strong Biomass Benzoxazine Resins via Green Strategy

Preparation of Thermally Resistant and Mechanically Strong Biomass Benzoxazine Resins via Green Strategy

Preparation of high‐performance hyperbranched polybenzoxazine with low dielectric constant

Design and Construction of Furan‐Based and Thiophene‐Based Salicyladazine Bisbenzoxazine Resins with High Thermal Stability and Tunable Surface Properties

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