N‐Hydroxyisoharnstoffe aus der Reaktion N‐substituierter Hydroxylamine mit Cyansäureestern

Neitzel, Michael; Zinner, G.

doi:10.1002/ardp.19813140103

Cited by 8 publications

(1 citation statement)

References 11 publications

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“…The Infrared spectroscopic (IR) spectrum of pCr‐DPEA in the solid state below 76°C strongly suggests that the ion dissociated state is preferred, and the hydrogen bonding state dominates in the molten state at 80°C (SI). On the other side, regarding the reactions of phenols or amines with the cyanate ester, cyanate esters does not only react with weakly acidic phenols 19 to form the triazine via an intermediate imino carbonate, but with nucleophilic amines rapidly to give cyanate‐amine adducts or triazines substituted with amino groups 20–22 . In the case of the addition of equal amounts of aromatic amines and phenols to cyanate esters, it has been found out that the products contain the imino carbonates and the cyanate‐amine adducts in the ratio of 1:2.…”

Section: Resultsmentioning

confidence: 99%

Investigation of the hardener with latent and rapid curing based on phenol‐amine salts for applications to cyanate ester resins

Ueyama

Ogawa²,

Tsuge

et al. 2021

J of Applied Polymer Sci

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We have developed the curing agents that have good storage stability for cyanate ester resins. It should be noted that these agents can be given rapid and efficient curing at low temperatures around 100°C. Even though the nucleophilicity was reduced by a phenol‐amine salts consisting of basic aliphatic amines and weakly acidic phenols, the curing reaction with the cyanate ester occurred immediately. It means that the control of the curing reaction with cyanate esters is not easy due to the equilibrium between phenol and amine. In order to overcome this difficultly cyanate esters reactivity, the molecular motions suppression by polymer was applied in addition to the phenol‐amine salts. The effect of the suppression for hardeners was studied in terms of the storage stability and reactivity to cyanate esters. It has been found out that PSM‐EPEDA composed of ethylenediamine‐epoxy adducts and novolac phenolic resin exhibits a large storage stability against cyanate esters by its effective suppression of molecular motions accompanied with efficient and rapid curing around 100°C.

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Section: Resultsmentioning

confidence: 99%

Investigation of the hardener with latent and rapid curing based on phenol‐amine salts for applications to cyanate ester resins

Ueyama

Ogawa²,

Tsuge

et al. 2021

J of Applied Polymer Sci

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Carbamoylierungs‐ und Cyclisierungsreaktionen an N‐Hydroxyisoharnstoffen

Neitzel

Zinner

1981

Archiv der Pharmazie

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N-Hydroxyisoharnstoffe 1 nehmen Phenylisocyanat an der HOGruppe auf und bilden die OCarbamoylverbindungen 4. Diese konnen zum A2-1,2,4-0xadiazolin-5-on (Sa), zu 3-Imino-1,2,4-oxadiazolidin-5-onen 5b-5e oder zum A3-l,2,4-0xadiazolin-5-on (9dB) cyclisieren. Die aus Sb-Se hergestellten Hydrochloride 6IAe sind zu den 1,2,4-Oxadiazolidin-3,5-dionen 7b-7e verseifbar. Die IR-und MS-Daten von 4,5,6 und 7 werden diskutiert. Acylalion and Qdization of NHydroxybmrem by Phenyl hcyanateOn adding phenyl isocyanate to the N-hydroxykoureas 1 the 0-carbamoyl derivatives 4 are obtained.They can undergo ring closure to yield A2-1,2,4-oxadiazolin-5-one (Sa), the 3-imino-1,2,4-oxadiazozolidin-5-ones S b S e or A3-1,2,4-oxadiazolin-5-one (9dB). Compounds 5b-Se form the hydrochlorides 6b-6e which can be hydrolized to yield the 1,2,4-oxadiazolidine-3,5-diones 7b-7e. The IR and MS data of compounds 4-7 are discussed.

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N‐Hydroxyisothioharnstoffe

Clement¹

1986

Archiv der Pharmazie

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Die Addition von Hydroxylamin an Alkylthiocyanate 1 fuhrt zu Gemischen, die uberwiegend aus 2-Alkyl-3-hydroxyisothioharnstoffen 2 und zum geringeren Teil aus S-Alkyithiocarbamaten 3 bestehen. Die Strukturaufklarung von 2a gelingt insbesondere durch Anwendung der "N-NMR-Spektroskopie. N-HydroxyisothioureasThe addition of hydroxylamine to alkyl thiocyanates I affords mixtures mainly of 2-alkyl-3-hydroxyisothioureas 2 and minor amounts of S-alkyl tbiocarbamtes 3. The structure of 2a has been elucidated by 15N-NMR spectroscopy.

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N‐Hydroxyisoharnstoffe aus der Reaktion N‐substituierter Hydroxylamine mit Cyansäureestern

Abstract: Addition von N-substituierten Hydroxylaminen an Cyansaureester (Phenyl-, 2,2,2-Trichlorethylund 2,2,2-Trifluorethylcyanat) liefert die N-Hydroxyisohamstoffe 4,s mit entsprechender Substitution.

Cited by 8 publications

References 11 publications

Investigation of the hardener with latent and rapid curing based on phenol‐amine salts for applications to cyanate ester resins

Investigation of the hardener with latent and rapid curing based on phenol‐amine salts for applications to cyanate ester resins

Carbamoylierungs‐ und Cyclisierungsreaktionen an N‐Hydroxyisoharnstoffen

N‐Hydroxyisothioharnstoffe

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