Well-defined benzoxazine/triphenylamine-based hyperbranched polymers with controlled degree of branching

Lin, Ruey-Chorng; Kuo, Shiao‐Wei

doi:10.1039/c8ra00506k

Cited by 25 publications

(13 citation statements)

References 61 publications

(122 reference statements)

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“…Besides dendritic, hyperbranched benzoxazine monomers based on trifunctional amine such as triphenyl amine (tpa) [ 150 ] and Jeffamine T-403 [ 151 ] with phenol and bisphenol A are also reported.…”

Section: Classification Of Benzoxazine Monomersmentioning

confidence: 99%

Review on the Accelerated and Low-Temperature Polymerization of Benzoxazine Resins: Addition Polymerizable Sustainable Polymers

et al. 2021

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Due to their outstanding and versatile properties, polybenzoxazines have quickly occupied a great niche of applications. Developing the ability to polymerize benzoxazine resin at lower temperatures than the current capability is essential in taking advantage of these exceptional properties and remains to be most challenging subject in the field. The current review is classified into several parts to achieve this goal. In this review, fundamentals on the synthesis and evolution of structure, which led to classification of PBz in different generations, are discussed. Classifications of PBzs are defined depending on building block as well as how structure is evolved and property obtained. Progress on the utility of biobased feedstocks from various bio-/waste-mass is also discussed and compared, wherever possible. The second part of review discusses the probable polymerization mechanism proposed for the ring-opening reactions. This is complementary to the third section, where the effect of catalysts/initiators has on triggering polymerization at low temperature is discussed extensively. The role of additional functionalities in influencing the temperature of polymerization is also discussed. There has been a shift in paradigm beyond the lowering of ring-opening polymerization (ROP) temperature and other areas of interest, such as adaptation of molecular functionality with simultaneous improvement of properties.

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Section: Classification Of Benzoxazine Monomersmentioning

confidence: 99%

Review on the Accelerated and Low-Temperature Polymerization of Benzoxazine Resins: Addition Polymerizable Sustainable Polymers

et al. 2021

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“…Studies have shown that benzoxazines with higher-order oxazine functionality from petroleum-derived multifunctional amines and phenolics produce polybenzoxazines with higher thermal stabilities, higher char yields, higher T g s, lower curing temperatures, and increased thermal processing windows. − Biobased benzoxazines with higher order oxazine functionality have been reported with minimal information regarding their thermomechanical and mechanical properties. ,− …”

Section: Introductionmentioning

confidence: 99%

Multifunctional Biobased Benzoxazines Blended with an Epoxy Resin for Tunable High-Performance Properties

Chong

Salazar

Stanzione

2021

ACS Sustainable Chem. Eng.

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Biobased polybenzoxazines incorporate natural phenolic structures to produce polymers with near-zero shrinkage, high char yields, and high chemical and thermal resistances, garnering great interest as sustainable high-performance polymers. Herein, difunctional and trifunctional benzoxazine monomers, bisguaiacol-furfurylamine (BG-f) and triguaiacol-furfurylamine (TG-f), respectively, were synthesized from renewable guaiacol, vanillin, and furfurylamine using solventless procedures. Benzoxazines were blended with varying weights of epoxy resin and thermally cured to produce benzoxazine-epoxy (BG-f-E and TG-f-E) polymers. These polymers displayed glass transition temperatures ranging from 130 to 157 °C (peak of the loss modulus), thermal stabilities from 299 to 329 °C in both N2 and air, and char yields ranging from 35% to 58%. BG-f-E and TG-f-E with greater benzoxazine content produced stiffer materials exhibiting glassy storage moduli values upward of 3.48 and 3.69 GPa, respectively. BG-f-E polymers displayed higher molecular weight between cross-link values (646 g mol–1 to 981 g mol–1) compared to TG-f-E polymers (316 g mol–1 to 465 g mol–1) and exhibited fracture energies upward of 404 J m–2. These investigations demonstrate the utility of incorporating biobased benzoxazines into benzoxazine-epoxy resin formulations to design sustainable polybenzoxazines with tunable thermal and mechanical properties for high-performance polymer applications.

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“…22,23 In contrast to P-a monomer, HB-PED230 has a dendritic-like structure with multiple branches and abundant terminal functional groups, which can improve the toughness of the copolymer. 24,25 In this work, a series of copolymers based on CE resin and HB-PED230 (CE/HB) were prepared and compared with (CE/P-a) copolymers. Compared to P-a, HB-PED230 has the advantages of longer flexible aliphatic chains and terminal hydroxyl groups, it is expected to improve mechanical properties and reduce the curing temperature of CE resin.…”

Section: Introductionmentioning

confidence: 99%

“…Fortunately, due to the superb molecular design flexibility of benzoxazines, this problem can be solved by the introduction of flexible aliphatic chains or hyperbranched structures 22,23 . In contrast to P‐a monomer, HB‐PED230 has a dendritic‐like structure with multiple branches and abundant terminal functional groups, which can improve the toughness of the copolymer 24,25 …”

Section: Introductionmentioning

confidence: 99%

Curing kinetics and mechanical properties of cyanate ester/hyperbranched benzoxazine copolymers

Wang

Qin

et al. 2022

Polymers for Advanced Techs

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In the current study, three different curing kinetics models were used to analyze the curing kinetics of hyperbranched benzoxazine (HB‐PED230) and monofunctional benzoxazine (P‐a) modified cyanate ester (CE) resin by non‐isothermal differential scanning calorimeter. Moreover, the effects of two benzoxazines on the copolymerization behavior, thermal stability, and mechanical properties of CE resin were studied. Compared with the P‐a modified CE resin, HB‐PED230 greatly reduces the curing temperature of the copolymer, while improving the bending strength and impact strength. The curing temperature of HB‐PED230 modified CE resin was 79°C lower than neat CE resin, while the CE/P‐a blended resin only reduce 48°C. As the amount of HB‐PED230 increased, the flexural strength and flexural modulus of the copolymers were improved. Surprisingly, when 7 wt% of HB‐PED230 was added, the impact strength of the copolymer was increased by 177.6%, implying that the toughness of CE resin had been greatly improved. Moreover, the fracture morphology of the copolymers was observed by scanning electron microscope. In summary, a small amount of HB‐PED230 blending can effectively improve the overall performance of CE resin.

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Well-defined benzoxazine/triphenylamine-based hyperbranched polymers with controlled degree of branching

Abstract: Different well-defined benzoxazine/triphenylamine based hyperbranched polymers with controlled degree of branching were prepared and discussed.

Cited by 25 publications

References 61 publications

Review on the Accelerated and Low-Temperature Polymerization of Benzoxazine Resins: Addition Polymerizable Sustainable Polymers

Review on the Accelerated and Low-Temperature Polymerization of Benzoxazine Resins: Addition Polymerizable Sustainable Polymers

Multifunctional Biobased Benzoxazines Blended with an Epoxy Resin for Tunable High-Performance Properties

Curing kinetics and mechanical properties of cyanate ester/hyperbranched benzoxazine copolymers

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