Origin of the Rapid Trimerization of Cyanate Ester in a Benzoxazine/Cyanate Ester Blend

Wang, Meng Wei; Jeng, Ru‐Jong; Lin, Ching Hsuan

doi:10.1021/acs.macromol.5b00334

Cited by 23 publications

(19 citation statements)

References 31 publications

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“…Further, it was proposed that the ring-opened oxazine rings insert into the triazine rings to form cyanurates and isocyanurates, which then probably further react with oxazine rings to form other structures [ 176 ]. Wang et al [ 178 ] proposed the benzoxazine ring itself catalyzes both trimerization of cyanate ester and isomerization (cyanurate to isocyanurate) reactions upon heating. They showed the possibility of ROP for benzoxazine at 30 °C as evident from Figure 14 i.…”

Section: Classification Of Benzoxazine Monomersmentioning

confidence: 99%

“… ( i ) Digital images of a 50 wt% methyl ethyl ketone solution of PH-oda/BADCY (Bisphenol A dicyanate ester) (1/1, mol/mol): ( a ) freshly prepared solution, and the thermally treated solution at ( b ) 30 °C for 24 h, ( c ) 50 °C for 4 h and ( d ) 100 °C for 2 h [ 178 ]. ( ii ) Proposed catalytic mechanism of benzoxazine to the trimerization of cyanate ester solutions [ 178 ]. Copyright 2015.…”

Section: Figurementioning

confidence: 99%

See 1 more Smart Citation

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%

Section: Figurementioning

confidence: 99%

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

et al. 2021

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“…The high reaction temperatures of MA groups, although might be reduced with Lewis base and Brønsted acid pendants, limit the developments of MA‐based thermosetting resins due to less processing convenience and high energy consumption. On the other hand, benzoxazine‐based thermosetting resins and their reactive blends with other thermosets have been widely reported. One drawback of the benzoxazine‐based resins is still high reaction temperatures, although it could be catalyzed with acidic compounds …”

Section: Introductionmentioning

confidence: 99%

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

Chen

Lin

Chiang

et al. 2016

Macromol. Rapid Commun.

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In this work, a cocatalytic effect between Meldrum's acid (MA) and benzoxazine (Bz) compounds has been explored to build up a self-promoting curing system. Consequently, the MA/Bz reactive blend exhibits a relatively low reaction temperature compared to the required temperatures for the cross-linking reactions of the pure MA and Bz components. This feature is attractive for energy-saving processing issues. Moreover, the thermosetting resins based on the MA/Bz reactive blends have been prepared. The MA component can generate additional free volume in the resulting resins, so as to trap air in the resin matrix and consequently to bring low dielectric constants to the resins. The MA-containing agent is an effective modifier for benzoxazine resins to reduce their dielectric constants.

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“…From the DSC curve of pure cyanate ester in Figure 4, it can be observed that the curing temperature of pure cyanate ester was in the range of 270 to 320°C without adding catalyst. But Figure 3 showed a lower curing temperature, which can be related to the promotion of active phenolic hydroxyl generated from ring-opening of oxazine ring [29][30][31]. Moreover, with the introduction of CE, the temperature of first exothermic peak in prepolymers decreased, indicating that copolymerization occurred between oxazine ring and cyanate ester.…”

Section: Results and Discussion 31 Curing Behaviors Of A-ph/cementioning

confidence: 95%

Copolymerization of phthalonitrile-based resin containing benzoxazine and cyanate ester: Curing behaviors, fiber-reinforced composite laminates and improved properties

Chen¹,

Ren²,

Chen³

et al. 2019

Express Polym. Lett.

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Curing behaviors and copolymerization mechanisms between phthalonitrile-based resin containing benzoxazine (A-ph) and cyanate ester (CE) were characterized and discussed. Results indicated that copolymerization between A-ph and CE were comprised of ring-opening polymerization of oxazine rings and ring-forming polymerization of cyanate and nitrile groups. From them, ring-opening of oxazine occurred preferentially, followed by ring-forming of cyanate and nitrile groups, which were promoted by active hydrogen and amine structures generated from ring-opening of oxazine. Moreover, with increasing the content of CE (≥40 wt%), self-polymerization of cyanate would dominate the components of the resulting composites and reduces the thermal stability of fiber-reinforced composite laminates. Additionally, mechanical properties of composite laminates were also affected by the content of CE. Composite laminates with 10 wt% CE showed the highest flexural strength (622 MPa). The improved mechanical properties were also verified with investigation of dynamic thermomechanical analysis and morphology of fracture surfaces. These findings are helpful to improve the thermosetting resins in terms of their chemical structure, material properties, and processability.

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Origin of the Rapid Trimerization of Cyanate Ester in a Benzoxazine/Cyanate Ester Blend

Cited by 23 publications

References 31 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

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

Copolymerization of phthalonitrile-based resin containing benzoxazine and cyanate ester: Curing behaviors, fiber-reinforced composite laminates and improved properties

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