In situ FTIR and DSC investigation on cure reaction of liquid aromatic dicyanate ester with different types of epoxy resin

Lin, Rong-Ho

doi:10.1002/1099-0518(20000815)38:16<2934::aid-pola110>3.0.co;2-b

Cited by 47 publications

(38 citation statements)

References 14 publications

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“…[23], not shown here for brevity). This suggests that polycyclotrimerization is the exclusive reaction in the neat aromatic dicyanate system and only one type of linkage (i.e., the sym-triazine ring) is formed during the whole course of the reaction with or without external catalysts [7,16,18,23,28]. Polycyclotrimerization of aromatic dicyanates proceeds via a combination of three functional groups to form a triazine ring, as illustrated in path 1 of Scheme 1.…”

Section: Resultsmentioning

confidence: 92%

“…The successive FTIR spectra of neat dicyanate showed that the disappearing absorption bands of the cyanate at 2267 and 2237 cm 21 were accompanied by the emerging absorptions of triazine at 1565 and 1366 cm 21 (see Ref. [23], not shown here for brevity). This suggests that polycyclotrimerization is the exclusive reaction in the neat aromatic dicyanate system and only one type of linkage (i.e., the sym-triazine ring) is formed during the whole course of the reaction with or without external catalysts [7,16,18,23,28].…”

Section: Resultsmentioning

confidence: 99%

“…Various aromatic dicyanates were substantially investigated in our laboratory on the cure kinetics and mechanisms of polycyclotrimerization [16 -18], effect of intramolecular cycles on the polycyclotrimerization [19,20], the glass transition temperature-conversion relationship in the polycyclotrimerization [21,22], the cure reaction of aromatic dicyanate ester with different type of epoxy resin [23] and the cure reaction of the dicyanate/diepoxide/diamine system [24]. The curing system of BMI/BADCy [17,25] blend without a specific catalyst was investigated and the crosslinking reactions between BMI and dicyanates were indeed detected in the FTIR spectra.…”

Section: Introductionmentioning

confidence: 99%

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Cure reactions in the blend of cyanate ester with maleimide

LIN¹

2004

Polymer

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Cure reactions of a bismaleimide (4,4 0 -bismaleimidodiphenylmethane, BMI) associated with a liquid aromatic dicyanate ester (1,1 0 -bis(4-cyanatophenyl)ethane, BEDCy) and with a powder type aromatic dicyanate ester (bisphenol A dicyanate, BADCy) were investigated by in situ FTIR and DSC dynamic scanning. In non-catalyzed blend systems, co-reactions between dicyanate ester and bismaleimide always occur, and hence the formation of pyrimidine and/or pyridine structures take place. Pyrimidine structures always predominate. Probable reaction paths were also proposed for various formulations of hybrid blends. In addition, N-phenylmaleimide (MI) and p-phenyl-phenylcyanate (SCy) were utilized as model compounds and mixed via a melting method and a solution method to explore the corresponding cure reactions by means of FTIR, DSC and NMR. 13 C NMR spectra of the model compounds demonstrated the formation of linkages of sym-triazine rings, pyrimidine structures, pyridine structures and dioxazine structures. The reaction mechanism or linkage structures produced in the model compound system studied may be somewhat different from those of the real system due to a diffusion effect in real systems or to the different activation energy in both systems. q

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Section: Resultsmentioning

confidence: 92%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Cure reactions in the blend of cyanate ester with maleimide

LIN¹

2004

Polymer

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“…The possible cross‐reactions between the cyanate and epoxy resin were also investigated via solid‐state NMR using monofunctional compounds 25. 26 In previous studies27 we have explored a possible reaction series in a real system of 1,1′‐bis(4‐cyanatophenyl)ethane (BEDCy) and 2,2‐bis(4‐glycidyloxyphenyl)propane (BADGE) through correlation of the in situ FT‐IR spectra and DSC thermograms in dynamic scanning mode.…”

Section: Introductionmentioning

confidence: 99%

In situ FT‐IR and DSC investigation on the cure reaction of the dicyanate/diepoxide/diamine system

Lin

Hsu

2001

Polymer International

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Cure reactions of a liquid aromatic dicyanate ester (1,1′‐bis(4‐cyanatophenyl)ethane, BEDCy) with a liquid bisphenol A epoxide (2,2‐bis(4‐glycidyloxyphenyl)propane, BADGE) and 4,4′‐diaminodiphenyl sulfone (DDS) were studied through correlation of the in situ FT‐IR spectroscopy and DSC in dynamic scanning mode. Before this system was examined, cure reactions of precursory systems of BADGE/DDS, BEDCy/BADGE and BEDCy/DDS were investigated separately. Cure reaction paths for each system are proposed. Some reactions in the precursory systems, such as polycyclotrimerization of dicyanate to form sym‐triazine and formation of alkyl isocyanurate, were not observed in the combined curing system BEDCy/BADGE/DDS. Four principal reaction paths are proposed for this curing system: (1) formation of oxazoline from the reaction between the epoxide and cyanate group; (2) reaction of epoxide with primary amine to form a hydroxyl group; (3) reaction of epoxide with the hydroxyl group to form an ether linkage; and (4) rearrangement of oxazoline to form oxazolidinone. Two distinct, but somewhat overlapping, exothermic peaks were observed on the DSC thermogram. The lower temperature peak on the DSC thermogram was primarily contributed by the first reaction path, whereas the higher temperature peak can mainly be attributed to the reaction paths 2, 3 and 4. © 2001 Society of Chemical Industry

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“…Among them, epoxies [5][6][7][8][9][10][11] and specially, bismaleimides [12][13][14][15] have evidenced great interest. Also, for improving their low fracture toughness, cyanate esters have been frequently modified by means of the addition of certain thermoplastics and elastomers.…”

Section: Introductionmentioning

confidence: 99%

Influence of phenoxy addition on the curing kinetics for uncatalyzed and catalyzed cyanate ester resin

Remiro

Caba

Mondragón

et al. 2010

J of Applied Polymer Sci

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The curing behavior of the dicyanate ester of bisphenol-A (DCBA) modified with poly(hydroxy ether of bisphenol-A) (phenoxy) is studied by differential scanning calorimetry in dynamic and isothermal tests at temperatures between 120 and 240 C. The addition of phenoxy to DCBA produces an increase in the reaction rate and a decrease in the temperature of maximum reaction rate for the uncatalyzed resin, and also for the system catalyzed with copper (II) acetyl acetonate/nonylphenol. The exothermic heat of curing for the mixtures is also dependent on the phenoxy content. These facts evidence a catalytic effect of phenoxy on the curing of the cyanate ester resin, even though an autocatalytic behavior is observed for all uncatalyzed DCBA/phenoxy mixtures. A simplified mechanistic kinetic model is used to calculate the kinetic parameters. For the uncatalyzed systems, a decrease in the kinetic constant for the initiation reactions, and an increase in the propagation constant are measured when the cyanate content increases. The thermal activation energy for the initiation reaction of the catalyzed systems is lower than that of the uncatalyzed ones, and it depends on the weight fraction of cyanate in the mixture.

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In situ FTIR and DSC investigation on cure reaction of liquid aromatic dicyanate ester with different types of epoxy resin

Cited by 47 publications

References 14 publications

Cure reactions in the blend of cyanate ester with maleimide

Cure reactions in the blend of cyanate ester with maleimide

In situ FT‐IR and DSC investigation on the cure reaction of the dicyanate/diepoxide/diamine system

Influence of phenoxy addition on the curing kinetics for uncatalyzed and catalyzed cyanate ester resin

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