Acceleration effect of ionic liquids on polycyclotrimerization of dicyanate esters

Fainleib, Alexander; Grigoryeva, Olga; Starostenko, Olga; Vashchuk, A.V.; Rogalsky, Sergiy; Grande, Daniel

doi:10.3144/expresspolymlett.2016.66

Cited by 11 publications

(12 citation statements)

References 33 publications

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“…The acceleration of the reaction is found to not be proportional to the concentration of IL in the present work at relatively high concentrations, with no significant difference observed between 8 and 20 wt % IL additives. Similar effects have been reported in the literature by Fainleib and coworkers . For example, Vashchunk et al .…”

Section: Discussionsupporting

confidence: 89%

“…As mentioned, the acceleration of the cyanate ester reaction on addition of the aromatic [BnzC 1 im][NTf 2 ] IL that is observed in the present work depends on temperature and is smaller than the acceleration reported by Fainleib and co‐workers for an aliphatic imidazolium IL, 1‐octyl‐3‐methylimidazolium tetrafluoroborate [C 8 C 1 im][BF 4 ] that increased the reaction rate at 150 °C of BEDCy by a factor of three or up to several orders of magnitude . We use a similarly structured cation aliphatic‐based IL but with a different anion, [C 9 C 1 im][NTf 2 ] to investigate the aromatic versus aliphatic nature of IL, and we found that the reaction rate was accelerated by a factor of approximately two, consistent with but slightly less than Fainleib's more recent work.…”

Section: Discussioncontrasting

confidence: 69%

“…Our results indicate a slight acceleration of the reaction kinetics at high temperatures and a higher activation energy with the addition of 8 wt % aromatic IL to BADCy. In contrast, Fainleib and coworkers found a greater acceleration for an aliphatic IL in BEDCy and at lower temperatures, with no perceptible reaction for the neat resin in 6 h at 150 °C compared to over 80% conversion when 5% aliphatic IL was added . In their recent work, the cure of BEDCy was three times faster when 1% aliphatic IL was added.…”

Section: Resultsmentioning

confidence: 87%

“…Similarly, Throckmorton and Palmese found that the cure of bisphenol E dicyanate ester (BEDCy) was accelerated with a reactive dicyanamide‐containing IL. In the case of non‐reactive IL additives, Fainleib and coworkers reported acceleration of BEDCy trimerization with the incorporation of an aliphatic imidazolium IL and an aliphatic pyridinium IL, as well as with hydroxy‐terminated and polymeric ILs, and they proposed a mechanism to explain the acceleration which involved formation of a cyanate ester/IL complex.…”

Section: Introductionmentioning

confidence: 99%

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Kinetic Study of Curing Bisphenol A Dicyanate Ester with Ionic Liquid Additive

Zhai

Quitevis

Simon

2019

J Polym Sci B Polym Phys

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A kinetic study of the trimerization reaction of bisphenol A dicyanate ester with an aromatic imidazolium-based ionic liquid (IL) as additive is performed using dynamic and isothermal differential scanning calorimetry. The reaction follows second-order autocatalytic kinetics, and a slight acceleration effect is observed in the presence of the aromatic IL relative to the neat resin. The activation energy also increases with the IL additive, whereas the glass transition temperature (T g ) is depressed, consistent with the Fox equation and a homogeneous one-phase material. A model incorporating diffusion effects is able to describe the dynamic and isothermal curing data for both the neat resin system and that containing aromatic IL. A comparison with aliphatic-based IL additive indicates that the reaction is more accelerated with aliphatic IL than with the aromatic IL in spite of the fact that the aliphatic additive phase separates during cure.

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Section: Discussionsupporting

confidence: 89%

Section: Discussioncontrasting

confidence: 69%

Section: Resultsmentioning

confidence: 87%

Section: Introductionmentioning

confidence: 99%

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Kinetic Study of Curing Bisphenol A Dicyanate Ester with Ionic Liquid Additive

Zhai

Quitevis

Simon

2019

J Polym Sci B Polym Phys

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“…However, the lowest changes were observed for the CER/[OMIm] [BF 4 ] network. This was probably due to the fact that [OMIm][BF 4 ] was not chemically embedded into the CER network structure [31]. Nevertheless, a slight decrease in T α and E′ values as well as an increase in tan δ max and ∆T values were evidenced, thus demonstrating a higher mobility of the kinetic segments between the cross-links of the CER matrix.…”

Section: Thermal Stability Of Cer-based Network By Tgamentioning

confidence: 99%

Effect of ionic liquids on kinetic parameters of dicyanate ester polycyclotrimerization and on thermal and viscoelastic properties of resulting cyanate ester resins

Fainleib¹,

Grigoryeva²,

Vashchuk³

et al. 2019

Express Polym. Lett.

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Cyanate ester resins (CERs) represent a family of thermosetting polymers possessing attractive intrinsic features, such as excellent dimensional stability, high glass transition temperature (T g > 250°С), low dielectric constants (2.5-3.2), flame-retardancy, and high adhesion to conductor metals and composites. Therefore, they are promising materials for aerospace and microelectronic applications, especially as polymer matrices for structural composites, adhesives, potting resins, and coatings that work under severe conditions (high temperature, humidity, corrosive media, etc) [1][2][3][4][5][6]. Dicyanate ester monomers undergo thermal polycyclotrimerization to generate high T g polycyanurate networks (PCNs), i.e. cyanate ester resins (CERs), without releasing volatile products. Figure 1 describes the reaction scheme of polycyclotrimerization of one of the widely used monomers, i.e. dicyanate ester of bisphenol E (DCBE). Dicyanate ester homopolymerization occurs at high temperature in the presence or the absence of a specific catalyst. The rate of non-catalyzed polycyclo -Abstract. A strong catalytic effect of 1.0 wt% ionic liquids (ILs) on kinetic parameters of dicyanate ester of bisphenol E (DCBE) polycyclotrimerization was evidenced, and structure-property relationships of resulting densely cross-linked cyanate ester resins (CERs) were investigated. Three different ILs with contrasted reactivity were employed as a catalysts: an aprotic IL, i.e. 1-octyl-3-methyl imidazolium tetrafluoroborate ([OMIm][BF 4 ]), a protic IL, i.e. 2-(hydroxyethylamino) imidazolinium chloride ([HEAIm][Cl]), and a protic polymeric IL, i.e. poly(hexamethylene guanidine) toluene sulfonate ([PHMG][TS]). Both [HEAIm][Cl] and [PHMG][TS] were reactive towards DCBE monomer, whereas [OMIm] [BF 4 ] was chemically inert, as confirmed by Fourier Transform Infrared (FTIR) spectroscopy. Noticeably, the conversion (α c ) of cyanate groups in the presence of ILs dramatically increased, and a significant dependence of α c values on IL chemical structure was found. The corresponding mechanisms of DCBE polycyclotrimerization in the presence of different ILs were proposed. All the CER/IL networks exhibited a high thermal stability inherent to neat CER, as shown by TGA, whereas unexpected significant changes of the viscoelastic characteristics for CER/IL networks compared to pure CER analogue were observed using DMTA.

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Reduced graphene oxide catalytically enhances the rate of cyanate ester curing under variable frequency microwave heating

Warner

Jeng

Ayar

et al. 2023

J of Applied Polymer Sci

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The curing of Lonza Primaset PT-30 novolac cyanate ester resin and EPON 826 bisphenol-A diglycidyl ether were investigated using convective thermal heating and variable frequency microwave (VFM) heating. The addition of 1 part per hundred reduced graphene oxide (r-GO) to PT-30 novolac cyanate ester increased the VFM cure rate compared to thermal heating. Curing it at 160 C for 240 min with VFM heating resulted in a 55% degree of cure compared to a 26% degree of cure with thermal heating. This observed VFM rate enhancement is due to selective microwave heating of the r-GO particles in the resin resulting in increased r-GO catalytic activity toward cyanate ester curing. It is both a thermal and catalytic effect, the latter of which is absent when r-GO is added to a bisphenol-A diglycidyl ether resin with ophenylenediamine hardener. Impurities present in the PT-30 matrix do not appear to contribute to its overall cure kinetics, nor do they participate in the observed VFM rate enhancement.

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Acceleration effect of ionic liquids on polycyclotrimerization of dicyanate esters

Cited by 11 publications

References 33 publications

Kinetic Study of Curing Bisphenol A Dicyanate Ester with Ionic Liquid Additive

Kinetic Study of Curing Bisphenol A Dicyanate Ester with Ionic Liquid Additive

Effect of ionic liquids on kinetic parameters of dicyanate ester polycyclotrimerization and on thermal and viscoelastic properties of resulting cyanate ester resins

Reduced graphene oxide catalytically enhances the rate of cyanate ester curing under variable frequency microwave heating

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