The Synthesis of Polycyanates by the Polycyclotrimerisation of Aromatic and Organoelement Cyanate Esters

Панкратов, В. А.; Виноградова, С. В.; Korshak, V.V.

doi:10.1070/rc1977v046n03abeh002132

Cited by 55 publications

(24 citation statements)

References 4 publications

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“…For the synthesis of new CE monomer, BPC15CN, the precursor of bisphenol was synthesized from 3-pentadecylphenol, which is in turn obtained from CNSL -a renewable resource materialby following the procedure reported in the literature. 24,27 The cyanation of bisphenols was carried out by following the protocol developed by Grigat and Putter. 10 The reaction involved the addition of triethylamine to …”

Section: Resultsmentioning

confidence: 99%

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Cyanate ester resins containing pentadecyl-substituted cyclohexyl moiety: Synthesis, curing and structure–property relationship

Kulkarni

Tawade

Wadgaonkar

2012

High Performance Polymers

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Cyanate ester (CE) monomers containing pentadecyl-substituted cyclohexyl moieties such as 1,1-bis(4-cyanatophenyl) 3-pentadecylcyclohexane and 1,1-bis(4-cyanatophenyl) cyclohexane were synthesized and characterized by Fourier transform infrared, proton-nuclear magnetic resonance ( 1 H-NMR) and carbon-nuclear magnetic resonance ( 13 C-NMR) spectroscopies as well as differential scanning calorimetry (DSC). Both 1,1-bis(4-cyanatophenyl) 3-pentadecylcyclohexane and 1,1-bis(4-cyanatophenyl) cyclohexane exhibited better processability coupled with lower melting points, lower cure onset with broad cure exotherm than the commercially available CE monomer, namely, 2,2-bis(4-cyanatophenyl) propane. Glass transition temperatures of cured 2,2-bis(4-cyanatophenyl) propane, 1,1-bis(4-cyanatophenyl) cyclohexane and 1,1-bis(4-cyanatophenyl) 3-pentadecylcyclohexane were observed to be 288 C, 302 C and 160 C, respectively. Cured 1,1-bis(4-cyanatophenyl) cyclohexane displayed higher storage modulus (1.59 Â 10 9 Pa) than 1,1-bis(4-cyanatophenyl) 3-pentadecylcyclohexane (1.07 Â 10 9 Pa) and 2,2-bis(4-cyanatophenyl) propane (1.39 Â 10 9 Pa). The order of thermal stability of cured polycyanurates was found to be 2,2-bis(4-cyanatophenyl) propane > 1,1-bis(4-cyanatophenyl)cyclohexane > 1,1-bis(4-cyanato phenyl) 3-pentadecylcyclohexane. The moisture absorption of cured resins derived from 1,1-bis(4-cyanatophenyl) 3-pentadecyl cyclohexane and 1,1-bis(4-cynatophenyl)cyclohexane was found to be lower than that of 2,2-bis(4-cynatophenyl) propane implying the role of pentadecyl substituent and/or cyclohexyl moiety in imparting hydrophobicity to the polycyanurates.

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Section: Resultsmentioning

confidence: 99%

“…24,25 Copper acetylacetonate was purchased from Sigma-Aldrich Inc. (St. Louis, Missouri, USA). Cyclohexanone, phenol and triethylamine were procured from Merck (Bangalore, Karnataka, India).…”

Section: Methodsmentioning

confidence: 99%

Cyanate ester resins containing pentadecyl-substituted cyclohexyl moiety: Synthesis, curing and structure–property relationship

Kulkarni

Tawade

Wadgaonkar

2012

High Performance Polymers

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“…Both the residual heat and T g methods have been studied. Unfortunately, even for the most studied system, bisphenol A dicyanate, reported enthalpy data is scattered from 23.2 to 28.4 kcal/eq.-OCN [23,24] making accurate conversion measurements difficult.…”

Section: Introductionmentioning

confidence: 99%

Curing of dicyanate ester/epoxy copolymers modified with polysiloxane and butadiene-acrylonitrile rubbers

Szeluga

Moryc

2011

J Therm Anal Calorim

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The cyanate ester (CE) and epoxy (EP) resins were cured together at various mass compositions. The curing behavior of CE and CE/EP systems was studied by means of differential scanning calorimetry (DSC) in nonisothermal conditions. The DSC measurements indicated that the curing reactions were dependent on the stoichiometric ratio of the mixtures and showed the dilution effect of the EP resin in the cyclotrimerization of the catalyzed CE resin. The CE and CE/EP (70/30) systems were modified using reactive liquid butadiene-acrylonitrile copolymer (ETBN) and polysiloxane core-shell (PS) elastomer. The influence of ETBN and PS on the curing process and glass transition temperature (T g ) of CE/EP systems was determined. The impact resistance characteristics of the completely cured systems indicated the influence of the modifiers and the EP content in the mixtures on its impact resistance.

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“…No secondary reactions take place or only to a very small extent, and thus, in the case of dicyanates, highly crosslinked polymers (so-called polycyanurates) with a very regular chemical structure are obtained. 28 As these monomers only have benzene rings and ether and ketone groups, when the reaction reaches completion the final resins would be fully aromatic crosslinked poly(aryl ether ketone)s (Fig. 1), the first polymers of this kind described in the literature to our knowledge.…”

Section: Thermal Characterization Of the Monomersmentioning

confidence: 98%

Synthesis and characterization of new dicyanate monomers. A way to obtain fully aromatic crosslinked poly(ether ketone)s

Marcos‐Fernández

Posadas

Rodrı́guez

et al. 1999

J. Polym. Sci. A Polym. Chem.

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Several aromatic mono‐ and dicyanate monomers bearing ether and ketone groups in the main chain have been synthesized through high‐yield reactions widely used in organic chemistry. FT‐IR and NMR were used to characterize these monomers and the intermediate products. The cyclotrimerization reaction was studied by DSC in monocyanate models, and the enthalpy of the reaction was determined. The value obtained was approximately 95 kJ/mol of cyanate irrespective of the substituent and symmetry of the substitution. For short dicyanates, cyclotrimerization did not reach completion, and for long dicyanates, the enthalpy of reaction could not be evaluated with accuracy. The resulting cured polycyanurates networks, due to the selectivity of the cyclotrimerization reaction, could be considered as true fully aromatic crosslinked poly(ether ketone)s with controlled structure. Tg values of the networks were above 180°C. The higher values were found for shorter dicyanates and for monomers with para substitution. The 1% and 5% weight loss values in nitrogen were above 310 and 380°C, respectively, with char yields in the range 50–60%. © 1999 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 37: 3155–3168, 1999

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The Synthesis of Polycyanates by the Polycyclotrimerisation of Aromatic and Organoelement Cyanate Esters

Cited by 55 publications

References 4 publications

Cyanate ester resins containing pentadecyl-substituted cyclohexyl moiety: Synthesis, curing and structure–property relationship

Cyanate ester resins containing pentadecyl-substituted cyclohexyl moiety: Synthesis, curing and structure–property relationship

Curing of dicyanate ester/epoxy copolymers modified with polysiloxane and butadiene-acrylonitrile rubbers

Synthesis and characterization of new dicyanate monomers. A way to obtain fully aromatic crosslinked poly(ether ketone)s

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