Chemie der Cyansäureester, I. Cyansäureester aus Hydroxylverbindungen und Halogencyan

Grigat, Ernst; Pütter, Rolf

doi:10.1002/cber.19640971107

Cited by 165 publications

(38 citation statements)

References 7 publications

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“…Cyanates may adhere to a variety of substrates, e.g. metals, glass and carbon fibres and cyanate adhesives have yielded values of [14][15][16][17][18][19][20] MPa (for lap shear strength) on 20224 T-3 aluminium alloy (some 50-100% higher than corresponding BADGE and TGDDM epoxy adhesives (cured with aromatic diamines), but it is their behaviour on silicon that is of particular interest in the microelectronics arena because of the ubiquity of this material in the formation of MCMs. Typically, the latter are formed from sequentially built layers of metallised conductors on ceramic or silicon substrates and unreinforced polymer dielectric films.…”

Section: Introductionmentioning

confidence: 99%

“…A number of synthetic routes to the preparation of cyanate monomers has been reported and reviewed comprehensively [13], although the most important commercial route, first reported by Grigat and Pütter some forty years ago [14,15] and involving the treatment of phenols with cyanogen chloride (or more typically cyanogen bromide in laboratory preparations such as the route reported in this work), still form the basis of modern methods, albeit in a modified form.…”

Section: Introductionmentioning

confidence: 99%

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Examination of the Thermal and Thermomechanical Behavior of Novel Cyanate Ester Homopolymers and Blends with Low Coefficients of Thermal Expansion

et al. 2009

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A new four-step synthetic method is presented and applied to the preparation of three novel dicyanate monomers that comprise aryl/alkylene ether backbones with high molecular flexibility in high purity. The multi-step route involves four individual high yielding steps (each greater than 70%), thus giving an overall reaction yields for all four steps between 42% and 50% depending on the length of the backbone. The products of all steps are characterised using Fourier transform infrared spectroscopy, 1 H nuclear magnetic resonance spectroscopy, elemental analysis and melting point determination. DSC and alysis of 'uncatalysed' samples (i.e. those polymerised thermally in absence of a specific catalyst) display relatively sharp melting endotherms ranging from 66ºC to 125ºC, depending on the length (and hence flexibility of the backbone). All monomers display broad polymerisation exotherms within close agreement (87 ± 2 kJ/mol. cyanate), although the polymerisations occur in different temperature regimes. When catalysed (aluminium(III) acetylacetonate/dodecylphenol), DSC reveals that the exothermic polymerisation peaks occur at significantly lower temperatures than the uncatalysed analogues and have much narrower profiles, but tend occur in a similar temperature regime (i.e. the peak maxima fall within 205 o C -216 o C).The recorded polymerisation enthalpies for the catalysed monomers are ca. 93 ± 9.9 kJ/mol.Assessment of the thermal stabilities of the cured polycyanurates using TGA shows that the polymers lose 5% of their masses by ca. 346-366 o C, comparable with the commercial dicyanate AroCy B10, despite the greater aliphatic character. DMTA analysis is performed on the homopolymer of the commercial dicyanate AroCy B10 to validate the method and the results obtained are consistent with published data. The T g values of the homopolymers of (4a), (4b) and (4c) are determined from the peak maxima of the loss tangent, tan δ and are found to be 221 o C (4a), 139 o C (4b), and 121 o C (4c) and fall in the expected order as the backbone chain length and hence flexibility is increased. The storage moduli at 25ºC for the binary blends are significantly lower than the respective homopolymers, but the reduction in E' over the temperature range 25ºC to 200ºC is significantly improved compared with AroCy B10. When combined with AroCy B10, binary blends showed a reduction in CTE of up to 12 ppm/°C while maintaining the same value of T g .

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Examination of the Thermal and Thermomechanical Behavior of Novel Cyanate Ester Homopolymers and Blends with Low Coefficients of Thermal Expansion

et al. 2009

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“…More than a hundred years later, in 1964, almost simultaneously in three workgroups, the main synthetic routes for the synthesis of cyanates were developed [8]- [10].…”

Section: Polycyanuratesmentioning

confidence: 99%

Progress in Recycling of Composites with Polycyanurate Matrix

Dreyer

Söthje²,

Bauer³

2014

ACES

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Thermoset based composites are used increasingly in industry for light weight applications, mainly for aircraft, windmills and for automobiles. Fiber reinforced thermoset polymers show a number of advantages over conventional materials, like metals, especially their better performance regarding their strength-to-weight ratio. However, composite recycling is a big issue, as there are almost no established recycling methods. The authors investigate the recyclability of polycyanurate homo-and copolymers with different recycling agents under different conditions. Also the influence of the recycling process on the most important reinforcement fibers, i.e. carbon-, glass-, aramid-, and natural-fiber is investigated. The authors find that: the recycling speed is not only dependent on the temperature, but also is significantly influenced by the particular recycling agents and the polycyanurate formulation. Hence, the stability against the recycling media can be adjusted over a broad range by adjusting the polymer composition. Furthermore, the authors find that the inorganic reinforcement fibers (carbon and glass) are almost unaffected by neither recycling agent at either temperature. Aramid-fibers degrade, depending on the particular recycling agent, from slightly up to extremely strong. This leaves one with the possibility to find a combination of matrix resin and recycling agent, which does not affect the aramid-fiber significantly. In the case of natural fibers, the dependence on the particular recycling media is very strong: some media do not affect the fiber significantly; others reduce the mechanical properties (tensile strength and elongation at break) significantly, and still others even improve both mechanical properties strongly. From the Recyclate, the authors synthesize and subsequently characterize a number of new polyurethane thermosets (foamed and solid samples) with different contents of recyclate, exhibiting Tg in the range of 60˚C to 128˚C.

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“…The solution was added dropwise to ice waThe dicyanate monomers were synthesized using a modified procedure reported by Grigat et al 4 ter. The precipitate was collected and washed…”

Section: General Procedures For the Preparation Ofmentioning

confidence: 99%

“…In the early 1960s, Grigat and Putter were the first to report the synthesis of Conventional electronic circuit boards are made stable aromatic cyanates. 4 Since then, mono-, from glass-fiber reinforced epoxy resins. Howdi-, and polyfunctional cyanates as well as other ever, they often fall short of the thermal and elecderivatives have been synthesized.…”

Section: Introductionmentioning

confidence: 99%

Thermal behavior and properties of naphthalene containing bismaleimide-triazine resins

Hwang

Wang

1998

J. Appl. Polym. Sci.

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A series of bismaleimidertriazine (BT) resins were prepared from various dicyanate esters and 2,7-bis(4-maleimidophenoxy)naphthalene (BMPN), which contains a naphthalene group and an aryl ether linkage in the backbone. Their curing behaviors were characterized by differential scanning calorimetry. The exotherm temperature and polymerization reactivity were strongly affected by the chemical structure of the various dicyanate ester monomer. Thermal behaviors were investigated by thermogravimetric analyses and dynamic mechanical analyses. The glass transition temperatures ( T g ) of these cured resins with bismaleimide/dicyanate ester at the 1/2 molar ratio were in the range of 250-322ЊC, and exhibited excellent thermal stability up to 400ЊC in nitrogen. These results provided a structure-properties relationship for the cured bismaleimidertriazine resins.

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Chemie der Cyansäureester, I. Cyansäureester aus Hydroxylverbindungen und Halogencyan

Cited by 165 publications

References 7 publications

Examination of the Thermal and Thermomechanical Behavior of Novel Cyanate Ester Homopolymers and Blends with Low Coefficients of Thermal Expansion

Examination of the Thermal and Thermomechanical Behavior of Novel Cyanate Ester Homopolymers and Blends with Low Coefficients of Thermal Expansion

Progress in Recycling of Composites with Polycyanurate Matrix

Thermal behavior and properties of naphthalene containing bismaleimide-triazine resins

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