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  • 1
    Electronic Resource
    Electronic Resource
    Functional polymers (1984)
    Springer
    Polymer bulletin 12 (1984), S. 237-243 
    Details
    ISSN: 1436-2449
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology , Mechanical Engineering, Materials Science, Production Engineering, Mining and Metallurgy, Traffic Engineering, Precision Mechanics , Physics
    Notes: Abstract Acrylates and methacrylates of 1,3(2,4-dihydroxyphenyl)-di(2H-benzotriazole) and 1,3(2,4,6-trihydroxyphenyl)-di(2H-benzotriazole) have been prepared by treating acrylic acid or methacrylic acid with N,N′-dicyclohexyl carbodiimide and then allowing this mixture to react with the phenolic ultraviolet absorbers to give 1,3[2-hydroxy-4-acryloxy(methacryloxy)phenyl]-di(2H-benzotriazole) and 1,3[2,6-dihydroxy-4-acryloxy(methacryloxy)phenyl]-di(2H-benzotriazole). The yield of the esters was from 10 to 30%; they were characterized by their infrared, 1H, and 13C NMR spectra; their polymerizability was demonstrated. The compounds had X of 330 to 335 nm with extinction coefficients ranging from 3.0 to 3.5×104 L/mol·cm.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00275974
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  • 2
    Electronic Resource
    Electronic Resource
    Functional polymers. XXVII: 2[2-hydroxy-4-acryloxy(methacryloxy)phenyl]2H-benzotriazole: Monomers, polymers, and copolymers (1984)
    Springer
    Monatshefte für Chemie 115 (1984), S. 853-868 
    Details
    ISSN: 1434-4475
    Keywords: 2(2-Hydroxyphenyl)2H-benzotriazole ; Polymerizable stabilizers ; Ultraviolet spectra
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung 2(2,4-Dihydroxyphenyl)2H-benzotriazol wurde mit 50% Ausbeute über die Kondensation vono-Nitrobenzoldiazoniumchlorid mit Resorcin, gefolgt von reduktiver Cyclisierung der ursprünglich erhaltenen Azoverbindung mit Zn/NaOH, erhalten. Die Kondensation des Diazonium-Salzes hatte unter sorgfältig kontrollierten Bedingungen und im sauren Medium zu erfolgen, da ansonsten „Bis“-Kondensation auftrat, die nach der reduktiven Cyclisierung 2(2,4-Dihydroxyphenyl)1,3-2H-dibenzotriazol ergab. 2(2,4-Dihydroxyphenyl)2H-benzotriazol wurde mit Acryoyl- bzw. Methacryloylchlorid zur Reaktion gebracht, wobei die Monoacetylierungsprodukte in über 60% Ausbeute gewonnen wurden. Die beiden Monomeren wurden homopolymerisiert und mit Styrol, Methylmethacrylat undn-Butylacrylat zu Polymeren hohen Molekulargewichts copolymerisiert. Die Inkorporierung von 2[2-Hydroxy-4-acryloxy (bzw. 4-methacryloxy)]2H-benzotriazol in das Copolymer erfolgte zwischen 1 und 10 mol% der Comonomer-Mischung. Die UV-Spektren der Monomeren, Homo- und Copolymeren sind angegeben.
    Notes: Abstract 2(2,4-Dihydroxyphenyl)2H-benzotriazole has been prepared in about 50% yield by condensation ofo-nitrobenzenediazonium chloride with resorcinol followed by reductive cyclization of the initially obtained azo compound with zinc and sodium hydroxide. The condensation of the diazonium salt had to be carried out under carefully controlled conditions and in acidic medium, otherwise “bis”-condensation occurred which, after reductive cyclization, yielded 2(2,4-dihydroxyphenyl)1,3-2H-dibenzotriazole. 2(2,4-Dihydroxyphenyl)2H-benzotriazole was allowed to react with acryloyl or methacryloyl chloride. Monoacylation in the 4-position occurred by interfacial acylation technique and 2[2-hydroxy-4-acryloxy (or 4-methacryloxy)]2H-benzotriazole was obtained in over 60% yield. The two monomers were homopolymerized and copolymerized with styrene, methyl methacrylate, andn-butyl acrylate to polymers of high molecular weight. Incorporation of 2[2-hydroxy-4-acryloxy (or 4-methacryloxy)]2H-benzotriazole into the copolymer was from 1 to 10 mol% of the comonomer mixture. The ultraviolet spectra of monomers, homo- and copolymers were also determined.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01120980
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  • 3
    Electronic Resource
    Electronic Resource
    Head-to-head polymers — XXXII: Toward head-to-head poly(α-methylstyrene): Synthesis of 2,3-dimethyl-2,3-diphenylbutanediol-1,4-ditosylate and 1,4-diphenyl-2,3-dimethylbutadiene-1,3 (1985)
    Springer
    Monatshefte für Chemie 116 (1985), S. 401-412 
    Details
    ISSN: 1434-4475
    Keywords: Phenonium rearrangement ; Nucleophilic displacement ; Stereoisomers ; 1H- and13C NMR
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Ausgehend von 2-Phenylpropionsäure (1) wurde 2,3-Dimethyl-2,3-butandiol-1,4-ditosylat (7) symthetisiert. Das Säurechlorid wurde bromiert und zu Methyl-2-phenyl-2-brom-propionat (4) umgesetzt, das mit Zink/Kupfer zu Dimethyl-2,3-dimethyl-2,3-diphenylsuccinat (5) gekuppelt wurde. Reduktion mitLAH zu 2,3-Dimethyl-2,3-diphenylbutandiol (6) und nachfolgende Tosylierung ergab eine Mischung der meso und racemischen Tosylate7a undb, welche in die reinen Isomere aufgetrennt werden konnten (a Fp. 170 °C undb Fp. 121 °C). Die beiden Verbindungen ergaben bei Behandlung mit Tetraalykylammoniumbromid nicht das erwartete 2,3-Dimethyl-2,3-diphenyl-1,4-dibrombutan (9), sondern 1,4-Diphenyl-2,3-dimethyl-butadien-1,3 (8). Das wurde durch unabhängige Synthese von8 auf anderem Wege, Vergleich der spektroskopischen Eigenschaften und mittels Mischschmelzpunkt nachgewiesen.
    Notes: Abstract 2,3-Dimethyl-2,3-diphenylbutanediol-1,4-ditosylate (7) was synthesized starting from 2-phenylpropionic acid (1). The acid chloride was brominated and transformed into methyl 2-phenyl-2-bromo-propionate (4) which was coupled with a zinc/copper couple to dimethyl 2,3-dimethyl-2,3-diphenylsuccinate (5). Reduction with lithium aluminum hydride to 2,3-dimethyl-2,3-diphenylbutanediol-1,4 (6) was followed by tosylation. The tosylate 7 a mixture of the meso and racemic compounds, could be separated into the pure isomers,a m. p. 170 °C andb m. p. 121 °C. The mixture of each individual pure compound, when treated with tetraalkyl-ammonium bromide, did not give the expected 2,3-dimethyl-2,3-diphenyl-1,4-dibromobutane (9) but rather 1,4-diphenyl-2,3-dimethylbutadiene-1,3 (8). The identity of the compound was established by independent unequivocal synthesis, the comparison of spectral characteristics, and mixed melting point.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00799974
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  • 4
    Electronic Resource
    Electronic Resource
    Esters of alternating copolymers of maleic or 2,3-dimethylmaleic anhydride with alkyl vinyl ethersThis paper is dedicated to Professor Junji Furukawa on the occasion of his seventieth birthday, with warmest personal wishes. (1983)
    New York : Wiley-Blackwell
    Journal of Polymer Science: Polymer Chemistry Edition 21 (1983), S. 891-911 
    Details
    ISSN: 0360-6376
    Keywords: Physics ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Maleic anhydride or 2,3-dimethylmaleic anhydride was copolymerized with a number of alkyl vinyl ethers, with AIBN as the initiator. The comonomers were always alternating and were obtained in yields ranging from 15 to 99%. The acid anhydride group in both series of copolymers was converted to the corresponding methyl esters in a two-step reaction. The structure of these polymers was established by elemental analysis and by infrared, 1H-and 13C-NMR spectroscopy. Addtional characterization of these copolymers were carried out by viscosity measurements, differential scanning calorimetry for the determination of glass transition temperatures, and thermal degradation for the determination of the thermal stability of the copolymers.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pol.1983.170210323
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  • 5
    Electronic Resource
    Electronic Resource
    Solution NMR study of the post-polymerization crosslinking agent N,N′-(2-propyloximino)-4,4′-methylenebis(phenylcarbamate). I (1984)
    New York, NY [u.a.] : Wiley-Blackwell
    Journal of Applied Polymer Science 29 (1984), S. 2299-2305 
    Details
    ISSN: 0021-8995
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Mechanical Engineering, Materials Science, Production Engineering, Mining and Metallurgy, Traffic Engineering, Precision Mechanics , Physics
    Notes: Because of its possible use as a blocked “post-polymerization crosslinking agent” for polymers containing labile hydrogen, the structure of the acetone oxime adduct of 4,4′-methylenebis-(phenylisocyanate) has been determined. 13C and 1H nuclear magnetic resonance (NMR) spectroscopy has identified this product to be N,N′-(2-propyloximino)-4,4′-methylenebis(phenylcarbamate). Chemical shift assignments were based on information obtained by proton decoupled, off-resonance decoupled, and gated decoupled 13C-NMR, proton-NMR, and semiemperical substituent chemical shift (SCS) parameters.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/app.1984.070290706
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  • 6
    Electronic Resource
    Electronic Resource
    An NMR study of the dissociation of N,N′-(2-propyloximino)-4,4′-methylenebis(phenylcarbamate) and its crosslinking of polymers containing labile hydrogens. II (1984)
    New York, NY [u.a.] : Wiley-Blackwell
    Journal of Applied Polymer Science 29 (1984), S. 2307-2315 
    Details
    ISSN: 0021-8995
    Keywords: Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology , Mechanical Engineering, Materials Science, Production Engineering, Mining and Metallurgy, Traffic Engineering, Precision Mechanics , Physics
    Notes: Nuclear magnetic resonance spectroscopy has been used to study the dissociation and reaction of N,N′-(2-propyloximino)-4,4′-methylenebis(phenylcarbamate), as a crosslinking agent for polymers containing labile hydrogens. The crosslinking of poly(acrylic acid), polyacrylamide, and poly(vinyl alcohol) was found to result upon heating each to 150°C for 10 min with this component at 2-10 wt %.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/app.1984.070290707
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  • 7
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    Functional polymers (1984)
    Springer
    Details
    Publication Date: 1984-09-01
    Print ISSN: 0170-0839
    Electronic ISSN: 1436-2449
    Topics: Chemistry and Pharmacology , Mechanical Engineering, Materials Science, Production Engineering, Mining and Metallurgy, Traffic Engineering, Precision Mechanics , Physics
    Published by Springer
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