Pyrogallol-based benzoxazines with latent catalytic characteristics: The temperature-dependent effect of hydrogen bonds on ring-opening polymerization

Lin, Run-Sheng; Zhu, Yan; Zhang, Yongjian; Wang, Lemeng; Yu, Shujuan

doi:10.1016/j.eurpolymj.2018.03.015

Cited by 34 publications

(18 citation statements)

References 56 publications

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“…The intermolecular hydrogen bonding -OH⋯N (of another benzoxazine molecule R1) changed preferentially to the -OH⋯π intramolecular hydrogen bonding OH….π-electron of the benzene ring as shown in Figure 68 b. As a result of these interactions, it may be anticipated that PG based benzoxazine monomer may show a lower T p and E a than 2-NP-3-apd [ 408 ].…”

Section: Acceleration Of the Rate Of Polymerization Via Intramolecular Interactionmentioning

confidence: 99%

“… ( a ) Existence of polar phenolic-OH in benzoxazine monomer assisting ROP reaction. ( b ) Proposed structure evolution of PG-a and PG-fa during the ROP process [ 333 , 408 ]. …”

Section: Figurementioning

confidence: 99%

“….π-electron of the benzene ring as shown in Figure 68b. As a result of these interactions, it may be anticipated that PG based benzoxazine monomer may show a lower T p and E a than 2-NP-3-apd [408].…”

Section: Influence Of Oxazine Ring-opening By Intramolecular Interactions: Neighboring Group Effect and 5-or 6-membered Ring H-bondingmentioning

confidence: 99%

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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: Acceleration Of the Rate Of Polymerization Via Intramolecular Interactionmentioning

confidence: 99%

“… ( a ) Existence of polar phenolic-OH in benzoxazine monomer assisting ROP reaction. ( b ) Proposed structure evolution of PG-a and PG-fa during the ROP process [ 333 , 408 ]. …”

Section: Figurementioning

confidence: 99%

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

et al. 2021

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“…1 The curing of the polybenzoxazine that undergoes the ring-opening polymerization is no small molecule release and near-zero volumetric shrinkage rate which overcomes several shortcomings of phenolic resins. 2 –4 Another advantage of polybenzoxazine is molecular design flexibility that prompts the development of a wide range of benzoxazine monomers having various functional groups. 5 –10 Therefore, polybenzoxazine has developed rapidly in the fields of aerospace industry, printed circuit boards, and composite materials during the past 30 years.…”

Section: Introductionmentioning

confidence: 99%

Effect of acetylacetone metal salts on curing mechanism and thermal stability of polybenzoxazine

Yan

Wang

et al. 2020

High Performance Polymers

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To overcome high water absorption of inorganic metal salts and their poor compatibility with resin, acetylacetone metal salts (M(acac) n) were selected as the catalysts of benzoxazine resin. Their effects on the catalytic activity, structure, and thermal stability of polybenzoxazine had been estimated by dynamic differential scanning calorimetry, in situ Fourier transform infrared spectroscopy, X-ray photoelectron spectroscopy, and thermal gravimetric analyzer. The results revealed that M(acac) n of iron (Fe3+), cobalt (Co3+ and Co2+), and copper (Cu2+) exhibited high catalytic activity and reduced evidently activation energy, especially acetylacetone iron salt. The addition of M(acac) n was beneficial to the formation of Ph–N–Ph structure, which was easy to form a denser carbon layer during thermal degradation, prevented heat transfer and further decomposition of the resin, and finally led to the increase of carbon residue at high temperature.

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“…3a,17 Another approach is to form intramolecular five- or six-membered hydrogen bonding to the oxazine ring, which significantly influences the ring-opening equilibrium. 18 Naturally, adding initiators and/or catalyst will help reduce the temperature as well. 14e,19 One popular approach is to understand the role of the substituent, either on the phenolic or amine moiety, in influencing the oxazine ring-opening equilibrium.…”

Section: Introductionmentioning

confidence: 99%

Development of Hydrogen-Rich Benzoxazine Resins with Low Polymerization Temperature for Space Radiation Shielding

et al. 2018

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A systematic study has been carried out to develop a material with significant protection properties from galactic cosmic radiation and solar energetic particles. The research focused on the development of hydrogen-rich benzoxazines, which are particularly effective for shielding against such radiation. Newly developed benzoxazine resin can be polymerized at 120 °C, which meets the low-temperature processing requirements for use with ultrahigh molecular weight polyethylene (UHMWPE) fiber, a hydrogen-rich composite reinforcement. This highly reactive benzoxazine resin also exhibits low viscosity and good shelf-life. The structure of the benzoxazine monomer is confirmed by proton nuclear magnetic resonance and Fourier transform infrared spectroscopy. Polymerization behavior and thermal properties are evaluated by differential scanning calorimetry and thermogravimetric analysis. Dynamic mechanical analysis is used to study chemorheological properties of the benzoxazine monomer, rheological properties of the cross-linked polybenzoxazine, and rheological properties of UHMWPE-reinforced polybenzoxazine composites. The theoretical radiation shielding capability of the composite is also evaluated using computer-based simulations.

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Pyrogallol-based benzoxazines with latent catalytic characteristics: The temperature-dependent effect of hydrogen bonds on ring-opening polymerization

Cited by 34 publications

References 56 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

Effect of acetylacetone metal salts on curing mechanism and thermal stability of polybenzoxazine

Development of Hydrogen-Rich Benzoxazine Resins with Low Polymerization Temperature for Space Radiation Shielding

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