Cyanuric chloride as a potent catalyst for the reduction of curing temperature of benzoxazines

Akkus, Buket; Kışkan, Barış; Yaǧcı, Yusuf

doi:10.1039/c9py01631g

Cited by 26 publications

(14 citation statements)

References 63 publications

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“…Amine HX salts reduce the ROP temperature, and reduction is found to be both cation and counter-ion dependence and follows the order of I − > Br − > Cl − [ 331 ]. Recently, cyanuric chloride (2,4,6-trichloro-1,3,5-triazine, TCT) was used as a miscible latent catalyst; it remained dormant at RT and was activated due to moisture or nucleophile to form HCl and cyanuric acid, which then catalyzes the ROP reaction [ 339 ].…”

Section: Acceleration Of the Rate Of Polymerization Via Intermolecular Interactionmentioning

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: Acceleration Of the Rate Of Polymerization Via Intermolecular Interactionmentioning

confidence: 99%

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

et al. 2021

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“…Although byproduct and formaldehyde release during the production of polybenzoxazines from their corresponding benzoxazine monomers is limited unlike classical phenolic resin production processes (Scheme ), some benzoxazine monomers could evaporate during curing due to the high polymerization temperatures (160–260 °C) usually applied. − However, in general, those volatile benzoxazines are low molar mass compounds, and actually most of the commercial monomers are solid. In order to reduce evaporation and increase processability, several strategies involving the use of polymeric benzoxazines as main-, side-, and end-chain precursors were proposed. − Additionally, ring-opening polymerization of benzoxazines can be catalyzed effectively by cationic species, acids, and even amines or some salts to reduce the curing temperatures for both energy efficiency and limiting the amount of monomer evaporation. − Although polybenzoxazine synthesis is relatively greener compared to classical phenolic resin production as a consequence of reactive nature of their monomers, high atom economy, and low byproduct emissions, benzoxazine resins are still facing environmental and ecological challenges similar to other fossil resource-based polymers.…”

Section: Introductionmentioning

confidence: 99%

Advanced Thermosets from Sulfur and Renewable Benzoxazine and Ionones via Inverse Vulcanization

Bayram

Kışkan

Demir

et al. 2020

ACS Sustainable Chem. Eng.

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An unprecedented synthesis of terpolymers from bioderived monomers and elemental sulfur in one-pot is described. In this approach, biosourced compounds, namely, vanilin and furfurylamine-based benzoxazine and ionones (and carvone), and a waste product of petroleum industry, sulfur, were reacted in one pot to produce an advanced thermoset. The inverse vulcanization of these compounds was monitored, and the properties of the obtained terpolymers were characterized via spectral and thermal characterization methods. Moreover, a potential use of the polymers as a Li−S battery cathode was demonstrated, and over 400 mAh/g capacity more than 100 of cycles were observed. Electrochemical impedance spectroscopy studies were used to gain more insight into the lithium storage mechanism before and after cycling.

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“…This phenomenon can be ascribed to hydroxyl groups on the external surface of HNTs, which have a positive effect on the curing reaction. 26,27 Figure 8 shows the DSC curves of DGEBA/B-HNTs system after different curing stages. The exothermic peak disappeared after heating at 220 C for 2 h, which indicated the curing reaction was completed.…”

Section: Dsc Analysis Of Dgeba/b-hnts Compositesmentioning

confidence: 99%

Preparation of benzoxazine-modified halloysite nanotubes and its application on epoxy/benzoxazine composites

Shen

Liu

et al. 2020

High Performance Polymers

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Benzoxazine monomer (named as B-aptes) was synthesized from 3-aminopropyltriethoxysilane (KH-550), bisphenol A (BPA), and paraformaldehyde. Subsequently, functionalized halloysite nanotubes were obtained by introducing B-aptes onto the surface of halloysite nanotubes (HNTs). Then, benzoxazine-modified halloysite nanotubes (B-HNTs) were used to combine with BPA epoxy resin to prepare the diglycidyl ether of bisphenol-A (DGEBA)/B-HNTs composites. The homogeneous dispersion state of modified HNTs in the cured composite matrix was observed by scanning electron microscopy. Differential scanning calorimetry was used to investigate polymerization behaviors of ternary composites. The results showed that the ternary composite possessed lower polymerization temperature compared with the neat DGEBA/benzoxazine. According to the results of thermogravimetric analysis, the thermal stability of DGEBA/benzoxazine copolymers was improved by the modified HNTs, the char yield increased with the increase of HNTs mass ratio. The results of mechanical tests and dynamic mechanical analysis displayed that the DGEBA/B-HNTs composites possessed promoted mechanical properties.

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Cyanuric chloride as a potent catalyst for the reduction of curing temperature of benzoxazines

Abstract: Cyanuric chloride (2,4,6-trichloro-1,3,5-triazine, TCT) was used as a catalyst to lower the ring opening polymerization (ROP) temperature of 1,3-benzoxazines.

Cited by 26 publications

References 63 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

Advanced Thermosets from Sulfur and Renewable Benzoxazine and Ionones via Inverse Vulcanization

Preparation of benzoxazine-modified halloysite nanotubes and its application on epoxy/benzoxazine composites

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