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  • 1
    Electronic Resource
    Electronic Resource
    Photo- and thermoinitiated curing of epoxy resins by sulfonium salts (1993)
    Weinheim : Wiley-Blackwell
    Angewandte Makromolekulare Chemie 209 (1993), S. 197-212 
    Details
    ISSN: 0003-3146
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Physics
    Description / Table of Contents: Eine Reihe von Benzylthiolaniumsalzen wurde präpariert, charakterisiert und mittels DSC-Messungen und Verfolgung des Viskositätsanstiegs hinsichtlich der Brauchbarkeit fur die thermische Härtung von Epoxidharzsystemen evaluiert. Es ergab sich uber einen weiten Bereich der Hammett-Konstanten eine Korrelation zwischen Startaktivität, Lagerstabilität und elektronischen Substituenteneinflüssen an der Benzylgruppe. Durch Kombination mit Arylsulfoniumsalzen erhält man in Einzelfällen Dual Cure Systeme mit attraktiven Eigenschaften sowohl für die thermische als auch für die UV-induzierte Härtung. Auch eine Sensibilisierung von Benzylthiolaniumsalzen erwies sich als gangbarer Weg zu Dual Cure Systemen. Somit eröffnen sich neue Einsatzmöglichkeiten für UV-härtbare Epoxidharzsysteme in der Elektronik, bei denen eine zusätzliche Härtung in abgeschatteten Bereichen unabdingbar ist.
    Notes: A number of benzylthiolanium salts have been synthesized, analysed and evaluated by differential scanning calorimetry and viscosity measurements with respect to their potential use as thermal curing agents for epoxy resins. Over a wide range of Hammett constants a correlation exists between initial reactivity, shelf life and the electronic substituent effects of the benzyl group. A combination with arylsulfonium salts leads in singular cases to dual cure systems with attractive properties of thermal and UV induced curing. The sensitization of benzylthiolanium salts also leads to dual cure systems. This opens up new possibilities for UV curable epoxy resins in electronic applications requiring additional curing in shaded areas.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/apmc.1993.052090118
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  • 2
    Electronic Resource
    Electronic Resource
    Teilsubstituierte Tetrazene (Me3E)nN4H4 - n (E = Si, Ge, Sn): Darstellung, Charakterisierung und Thermolyse (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 2886-2899 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Partially Substituted Tetrazenes (Me3E)nN4H4 - n (E = Si, Ge, Sn): Preparation, Characterization, and Thermolysis1)Partially substituted tetrazenes (Me3E)nN4H4 - n (E = Si, Ge, Sn) can be prepared by protolysis of higher substituted tetrazenes (Me3E)oN4H4 - o (O 〉 n) or by silylation, germylation, or stannylation of lower substituted tetrazenes (Me3E)mN4H4 - m (m 〈 n). The obtained tetrazenes (Tab. 1) are colorless compounds; they have 2-tetrazene constitution, and trans-tetrazene configuration. The tetrazene (Me3Si)2N  -  N = N  -  NHX (X = H or GeMe3) isomerize by heating in dilute solution into (Me3Si)XN  -  N = N  -  NH(SiMe3). The thermolysis of (Me3Si)2N  -  N = N  -  NH(SiMe3) leads mainly to Me3SiN3 and (Me3Si)2NH (t140°C1/2140°C = 3/4 h), of (Me3Si)2N  -  N = NH2 to Me3SiN3 and Me3SiNH2 (concentrated solution; t140°C1/240°C ca. 1/4 h), and of (Me3Si)HN  -  N = N  -  NH(SiMe3) to N2 and (Me3Si)2N  -  NH2 (dilute solution; t140°C1/2140°C 〉 1 h) or to NH3 and (Me3Si)2NH (concentrated solution; t140°C1/2 〈 1 h).
    Notes: Teilsubstituierte Tetrazene (Me3E)nN4H4 - n (E = Si, Ge, Sn) können durch Protolyse höher substituierter Tetrazene (Me3E)oN4H4 - o (O 〉 n) oder durch Silylierung, Germylierung bzw. Stannylierung niedriger substituierter Tetrazene (Me3E)mN4H4 - m (m 〈 n) dargestellt werden. Die gewonnenen Tetrazene (Tab 1) sind farblose Verbindungen: sie haben 2-Tetrazen-Konstitution und trans-Tetrazen-Konfiguration. Die Tetrazene (Me3Si)2N  -  N = N  -  NHX (X = H oder GeMe3) isomerisieren sich in verdünnter Lösung beim Erhitzen in (Me3Si)XN  -  N = N  -  NH(SiMe3). Die Haupttermolyse von (Me3Si)2N  -  N = N  -  NH(SiMe3) führt zu Me3SiN3 und (Me3Si)2NH (t140°C1/2140°C = 3/4 h), von (Me3Si)2 (Me3Si)2N  -  N = NH2 zu Me3SiN3 und Me3SiNH2 (konzentrierte Lösung; t140°C1/240°C ca. 1/4 h) und von (Me3Si)HN  -  N = N  -  NH(SiMe3) zu N2 und (Me3Si)2N  -  NH2 (verdünnte Lösung; t140°C1/2140°C 〉 1 h) oder zu NH3t140°C und (Me3Si)2NH (Konzentrierte Lösung; t140°C1/2140°C 〈 1 h).
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841170910
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  • 3
    Electronic Resource
    Electronic Resource
    Decarboxylierungsprodukt von Hexahydrophthalsäureanhydrid: Struktur und spektroskopische Eigenschaften (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 3413-3418 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Product of Decarboxylation of Hexahydrophthalic Anhydride: Structure and Spectroscopic PropertiesThe decarboxylation of some dicarboxylic anhydrides by catalytic influence of tertiary amines occurs at surprisingly low temperature (T≥80°C). The product 12, formed from two molecules of hexahydrophthalic anhydride 6 with loss of one molecule of carbon dioxide, has been isolated and characterized by spectroscopic investigations and X-ray structure analysis.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851180838
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  • 4
    Electronic Resource
    Electronic Resource
    Vierfach substituierte Tetrazene (Me3E)2N—N = N—N(EMe3)2 (E = Si, Ge, Sn): Darstellung, Charakterisierung und Zersetzung (1979)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 112 (1979), S. 2718-2729 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Tetrasubstituted Tetrazenes (Me3E)2N—N = N—N(EMe3)2 (E = Si, Ge, Sn): Preparation, Characterization, and DecompositionTetrakis(trimethylsilyl)tetrazene (1) is formed in almost quantitative yield by the catalytic dimerization of bis(trimethylsilyl)diazene with silicon tetrafluoride. The tetrazene N4H4, obtained as a result of protolysis of 1 with trifluoroacetic acid, is converted quantitatively into tetrakis-(trimethylgermyl)tetrazene (2) and tetrakis(trimethylstannyl)tetrazene (3) by Me3ENR2 (E = Ge, Sn). The colourless, crystalline tetrazenes 1-3 have 2-tetrazene constitution, trans-configuration and planar conformation of E4N4-skeleton. The thermolysis of the tetrazenes above 100-150°C occurs under nitrogen evolution mainly into (Me3Si)2NH for 1, (Me3Ge)4N2 for 2, and a mixture of (Me3Sn)3N and (Me3Sn)2 for 3. The tetrazenes 1 and 2 photolyse easily to (Me3E)3N and Me3EN3, whereas 3 reacts by photolysis to form (Me3Sn)3N, (Me3Sn)2, and N2.
    Notes: Tetrakis(trimethylsilyl)tetrazen (1) entsteht in fast quantitativer Ausbeute durch katalytische Dimerisierung von Bis(trimethylsilyl)diazen mit Siliciumtetrafluorid. Das aus 1 durch Protolyse mit Trifluoressigsäure erhältliche Tetrazen N4H4 läßt sich mittels Me3ENR2 (E = Ge, Sn) quantitativ in Tetrakis(trimethylgermyl)tetrazen (2) sowie Tetrakis(trimethylstannyl)tetrazen (3) umwandeln. Die farblosen, kristallisierten Tetrazene 1-3 haben 2-Tetrazen-Konstitution, trans-Konfiguration sowie planare Konformation des E4N4-Gerüsts. Die Thermolyse der Tetrazene oberhalb von 100-150°C führt unter Stickstoffentwicklung hauptsächlich zu (Me3Si)2NH im Falle von 1, (Me3Ge)4N2 im Falle von 2 sowie einem Gemisch von (Me3Sn)3N und (Me3Sn)2 im Falle von 3. Die Tetrazene 1 und 2 photolysieren rasch in (Me3E)3N und Me3EN3, während 3 photolytisch in (Me3Sn)3N, (Me3Sn)2 und N2 übergeht.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19791120740
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  • 5
    Electronic Resource
    Electronic Resource
    Vierfach substituierte Tetrazene (Me3E)2N—N=N—N(EMe3)2 (E=Si, Ge, Sn): Reaktivität (1980)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 113 (1980), S. 2916-2927 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Tetrasubstituted Tetrazenes (Me3E)2N—N=N—N(EMe3)2 (E=Si, Ge, Sn): ReactivityBy Substitution of the silyl, germyl, or stannyl groups, (Me3Si)2N—N=N—N(SiMe3)2 (1) reacts with variable amounts of trifluoroacetic acid to form (Me3Si)4-nN4Hn, (Me3Ge)2N—N=N—N(GeMe)2 (2) with variable amounts of methanol to form (Me3Ge)4-nN4Hn, and (Me3Sn)2N—N=N—N(SnMe3)2 (3) with variable amounts of trimethylchlorosilane to give (Me3Sn)4-nN4(SiMe3)n (n = 1-4). The reaction of 1 with benzenesulfonyl isocyanate leads by substitution and cyclization to silylated 5-hydroxytetrazole 12. Substitution in connection with thermolysis of the substitution products formed is found in the reaction of 1 with methanol, aluminium chloride, or nitrosyl chloride and in the reaction of 3 with trimethylstannane, acetone, or nitrosobenzene. By oxidation of 1 with chlorine, bromine, or p-benzoquinone and of 3 with p-benzoquinone or oxygen, all tetrazene nitrogen is evolved. The reduction of 1 with hydrogen or alkali metals leads to nitrogen and (Me3Si)2NH or (Me3Si)2NM.
    Notes: Unter Substitution der Silyl-, Germyl- bzw. Stannylgruppen reagieren (Me3Si)2 N—N=N—N-(SiMe3)2 (1) mit variablen Mengen Trifluoressigsäure zu (Me3Si)4-nN4Hn, (Me3Ge)2 N—N=N—N-(GeMe3)2 (2) mit variablen Mengen Methanol zu (Me3Ge)4-nN4Hn und (Me3Sn)2 N—N=N—N-(SnMe3)2 (3) mit variablen Mengen Trimethylchlorsilan zu (Me3Sn)4-nN4 (SiMe3)n (n = 1-4). Die Reaktion von 1 mit Benzolsulfonylisocyanat führt unter Substitution und Cyclisierung zu einem silylierten 5-Hydroxytetrazol 12. Substitution, verbunden mit einer Thermolyse des gebildeten Substitutionsproduktes, wird im Falle der Umsetzung von 1 mit Methanol, Aluminiumchlorid und Nitrosylchlorid bzw. von 3 mit Trimethylstannan, Aceton und Nitrosobenzol beobachtet. Durch Oxidation von 1 mit Chlor, Brom und p-Benzochinon bzw. von 3 mit p-Benzochinon und Sauerstoff wird der gesamte Tetrazenstickstoff freigesetzt. Die Reduktion von 1 mit Wasserstoff bzw. Alkalimetallen M führt zu Stickstoff sowie (Me3Si)2NH bzw. (Me3Si)2NM.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19801130909
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  • 6
    Electronic Resource
    Electronic Resource
    Darstellung silylierter Lithium-tetrazenide (1981)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 114 (1981), S. 2658-2660 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Preparation of Silylated Lithium TetrazenidesReaction of butyllithium with tris- or bis(trimethylsilyl)tetrazene, (Me3Si)3N4H or (Me3Si)2N4H2, lead to tetrazenides 1-3 which are sensitive in hydrolysis and thermolysis as well as against oxygen. Reactions (1)-(6) refer to their modes of thermolysis.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19811140730
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  • 7
    Electronic Resource
    Electronic Resource
    Isolierung von Tetrazen, N4H4 (1975)
    Weinheim : Wiley-Blackwell
    Zeitschrift für die chemische Industrie 87 (1975), S. 202-203 
    Details
    ISSN: 0044-8249
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/ange.19750870611
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  • 8
    Electronic Resource
    Electronic Resource
    Photoelektronen-Spektrum von Tetrazen (1975)
    Weinheim : Wiley-Blackwell
    Zeitschrift für die chemische Industrie 87 (1975), S. 203-204 
    Details
    ISSN: 0044-8249
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/ange.19750870612
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  • 9
    Electronic Resource
    Electronic Resource
    Isolation of Tetrazene, N4H4Part 3 of Tetrazene and Its Derivatives. This work was supported by the Deutsche Forschungsgemeinschaft. - Part 2: N. Wiberg and W. Uhlenbrock, Chem. Ber. 105, 63 (1972); Part 1:[4] (1975)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 14 (1975), S. 177-178 
    Details
    ISSN: 0570-0833
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.197501771
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  • 10
    Electronic Resource
    Electronic Resource
    Photoelectron Spectrum of TetrazenePart 4 of Tetrazene and Its Derivatives. This work was supported by the Deutsche Forschungsgemeinschaft. - Part 3: N. Wiberg, H. Bayer, and H. Bachhuber, Angew. Chem. 87, 202 (1975); Angew. Chem. internat. Edit. 14, 177 (1975). (1975)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 14 (1975), S. 178-179 
    Details
    ISSN: 0570-0833
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.197501781
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