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  • 1
    Electronic Resource
    Electronic Resource
    Aromatic Polyamides and Polyimides with Benzoxazole or Benzothiazole Pendent Groups Prepared from 5-(2-Benzoxazole)- or 5-(2-Benzothiazole)-1,3-phenylenediamine (1995)
    s.l. : American Chemical Society
    Macromolecules 28 (1995), S. 5177-5183 
    Details
    ISSN: 1520-5835
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology , Physics
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1021/ma00119a003
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  • 2
    Electronic Resource
    Electronic Resource
    Polymerization of maleimides containing s-triazine rings in presence of aromatic di- or tri-amines (1987)
    Springer
    Polymer bulletin 18 (1987), S. 1-8 
    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: Summary New thermosetting resins were prepared by crosslinking of 2,4,6-tris[4-(maleimido) phenoxy]-s-triazine (TM) or 2,4-bis[4-(maleimido) phenoxy]-6-diethoxyphosphinyl-s-triazine (BM) in presence of various aromatic di- or tri-amines. The maleimide-amine adducts initiated thermal polymerization at lower temperature than did the corresponding neat maleimides. The thermal stability of cured resins was evaluated by thermogravimetric analysis. The cured resins derived from the maleimide-amine adducts were less thermally stable than those of the corresponding neat maleimides. The initial decomposition temperature of the polymers obtained from the maleimide-amine adducts was not remarkably influenced by the chemical structure of the aromatic amine utilized.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00255814
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  • 3
    Electronic Resource
    Electronic Resource
    Flameproofing of cellulose and several synthetic polymers by substituted N-[(phosphinyl) methyl]-2-imidazolidinones (1985)
    Weinheim : Wiley-Blackwell
    Angewandte Makromolekulare Chemie 136 (1985), S. 115-128 
    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: Zur Entwicklung einer neuen Bearbeitungsmethode, mit deren Hilfe ein Stoff aus Baumwolle feuer- und knitterfest wird, wurden substituierte 1-[(Phosphinyl)methyl]-2-imidazolidinone verwendet. Der Prozeß schließt eine Behandlung des baumwollenen Stoffes mit einer sauren Lösung der substituierten 1-[(Phosphinyl)methyl]-3-hydroxymethyl-2-imidazolidinone und Tris(N-hydroxymethyl)melamine ein; danach folgt eine thermische Aushärtung. Zur Bewertung des Prozesses wurden die Feuer-, Knitter- und mechanische Festigkeit des bearbeiteten Stoffes bestimmt. Insbesondere wurde die Feuerfestigkeit der Proben durch Messung ihrer Verbrennungslänge und der Zeit ihres Nachbrennens und Nachgluhens bestimmt. Alle behandelten Proben waren selbstlöschend. Die Knitter- und mechanische Festigkeit der Proben wurde durch Messung ihres Rückzugswinkels bzw. der Reißfestigkeit bestimmt. Zusätzlich wurden die substituierten 1,3-Bis[(phosphinyl)methyl]-2-imidazolidinone bei einigen Kunststoffen wie Nylon 66 und Polyethylen als feuerfeste Beimischung verwendet. Das hatte eine Erhöhung des Sauerstoffindex (limiting oxygen index) dieser Kunststoffe zur Folge.
    Notes: Substituted 1-[(phosphinyl)methyl]-2-imidazolidinones were used for development of a novel finishing process referring cotton fabric fire and crease resistant. The process involves treatment of cotton fabric with an acidic solution of substituted 1-[(phosphinyl)methyl]-3-hydroxymethyl-2-imidazolidinones and tris (N-hydroxymethyl) melamine followed by curing. The fire resistance, the crease resistance, and the mechanical strength of the treated fabric were determined in order to evaluate the process. Particularly, the fire resistance of the specimens was determined by measuring their char length, the afterflame time, and the afterglow time. All treated specimens were selfextinguishing. The crease resistance and the mechanical strength of the specimens were determined by measuring their recovery angle and breaking load, respectively. In addition, substituted 1,3-bis[(phosphinyl)methyl]-2-imidazolidinones were used as fire retardant additives in several synthetic polymers such as nylon 66 and polyethylene with significant increase of their limiting oxygen index (LOI) value.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/apmc.1985.051360108
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  • 4
    Electronic Resource
    Electronic Resource
    Synthesis and characterization of nadimidized 1-[(dialkoxyphosphinyl)methyl1]-2,4- and -2,6- diaminobenzenes and their polymerization to fire-resistant laminating resins (1984)
    New York : Wiley-Blackwell
    Journal of Polymer Science: Polymer Chemistry Edition 22 (1984), S. 3535-3548 
    Details
    ISSN: 0360-6376
    Keywords: Physics ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A series of nadimidized 1-[(dialkoxyphosphinyl1)methyl]-2,4- and -2,6-diaminobenzenes was prepared and polymerized thermally to yield highly crosslinked fire-resistant laminating resins. Bisnadimides were characterized by elemental analysis and Fourier-transform-infrared (FT-IR) and proton nuclear magnetic resonance (1H-NMR) spectroscopy. Curing behavior of the polymer precursors was studied by differential scanning calorimetry (DSC). Char yield of polymers at 700°C was 64-69% and 30-60% in nitrogen and air atmospheres, respectively. The pyrolysis behavior of some bisnadimides was investigated by gas chromatography-mass spectroscopy (GC-MS). Cyclopentadiene was evolved by retrograde Diels-Alder reaction during processing, but most was captured by copolymerization. The fire-resistance of some polymers was evaluated by determining their limiting oxygen index and smoke evolution.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pol.1984.170221164
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  • 5
    Electronic Resource
    Electronic Resource
    Fire-resistant polyimides and copolyimides based on 1-[(dialkoxyphosphinyl)methyl]-2,4- and -2,6-diaminobenzenes (1984)
    New York : Wiley-Blackwell
    Journal of Polymer Science: Polymer Chemistry Edition 22 (1984), S. 1065-1076 
    Details
    ISSN: 0360-6376
    Keywords: Physics ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Various phosphorus-containing polyimides were prepared by the reaction of 1-[(dialkoxyphosphinyl)methyl]-2,4- and -2,6-diaminobenzenes (1) with a tetracarboxylic dianhydride like pyromellitic dianhydride (PMDA) and benzophenone tetracarboxylic dianhydride (BTDA). In addition, copolyimides that contained approximately 3% phosphorus were prepared by the reaction of 1 and m-phenylenediamine (MPD) with the aforementioned tetracarboxylic dianhydrides. Elemental analysis, inherent viscosity, infrared (IR) spectroscopy, differential scanning calorimetry (DSC), and thermogravimetric analysis (TGA) studies were performed to characterize the polymers. Their thermal properties were compared with those of the corresponding common polyimides. It was shown that the molecular weight and thermal stability of the polymers were reduced as the concentration of the phosphorus moieties increased. The fire-resistance of the copolyimides was evaluated by determining their limiting oxygen index (LOI) value. Copolyimides that contained about 3% phosphorus showed an LOI value approximately 30% higher, than the value of the corresponding common polyimides. In addition, a model diamic acid and diimide was synthesized by the reaction of 1-[di(2-chloroethoxyphosphinyl)methyl]-2,4- and - 2,6-diaminobenzene (DCEPD) with phthalic anhydride and characterized by elemental analysis, IR, proton nuclear magnetic (1H-NMR) spectroscopy, DSC, and TGA. The pyrolysis behavior of the model compounds was investigated by gas chromatography-mass spectrometry (GC-MS). A direct cleavage of the P—C bond and a possible rearrangement to diisocyanates occurred during their pyrolysis.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pol.1984.170220507
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  • 6
    Electronic Resource
    Electronic Resource
    Fire- and heat-resistant adhesive resins based on maleimido and citraconimido substituted 1-[(dialkoxyphosphinyl)methyl]-2,4- and -2,6-diaminobenzenes (1984)
    New York : Wiley-Blackwell
    Journal of Polymer Science: Polymer Chemistry Edition 22 (1984), S. 1717-1732 
    Details
    ISSN: 0360-6376
    Keywords: Physics ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A novel class of fire- and heat-resistant bisimide resins was prepared by thermal polymerization of maleimido or citraconimido derivatives of 1-[(dialkoxyphosphinyl)methyl]-2,4- and -2,6-diaminobenzenes (1). The neat bisimide resin prepared by curing 1-[di(2-chloroethoxyphosphinyl)methyl]-2,4- and -2,6-bismaleimidobenzene exhibited a limiting oxygen index 75% higher and smoke evolution about 30 times lower compared with the parent polymer obtained by curing m-phenylenebismaleimide. The char yield of cured bisimide resins at 700°C was 58-70% in a nitrogen atmosphere and 35-60% in air. An increase in formula weight between the imide groups slightly reduced the char yield. The polymer precursors were synthesized by reacting the phosphorus-containing diamines (1) (1 mol) with maleic anhydride/citraconic anhydride (2 mol) or by reacting the monomaleimido derivative of (1) with benzophenone tetracarboxylic dianhydride/methylenebis(4-phenylisocyanate) in a 2:1 mole ratio. The monomers were characterized by elemental analysis, Fourier-transform-infrared (FT-IR), proton nuclear magnetic resonance (1H-NMR) spectroscopy, and gas chromatography-mass spectroscopy (GC-MS). Direct cleavage of the P—C bond and inversion of the synthesis reaction may occur during their pyrolysis. The thermal polymerization of the monomers was investigated by differential scanning calorimetry (DSC). Biscitraconimides are thermally polymerized at a relatively lower temperature than the corresponding bismaleimides.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pol.1984.170220717
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  • 7
    Electronic Resource
    Electronic Resource
    Synthesis and thermal characteristics of phosphorus-containing polyureas and copolyureas based on 1-[(dialkoxyphosphinyl)methyl]-2,4- and -2,6-diaminobenzenes (1984)
    New York : Wiley-Blackwell
    Journal of Polymer Science: Polymer Chemistry Edition 22 (1984), S. 3423-3437 
    Details
    ISSN: 0360-6376
    Keywords: Physics ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The reactions of 1-[(dialkoxyphosphinyl)methyl]-2,4- and -2,6-diaminobenzenes (1) with various diisocyanates such as tolylene diisocyanate, methylenebis(4-phenylisocyanate), and hexamethylene-1,6-diisocyanate were studied for the synthesis of phosphorus-containing polyureas. Furthermore, diamines 1 were used as comonomers for preparing fire-resistant copolyureas. In addition, the corresponding common polyureas were synthesized for comparative purposes. All polymers were characterized by elemental analysis, inherent viscosity measurements, infrared (IR) and proton nuclear magnetic resonance (1H-NMR) spectroscopy, differential scanning calorimetry (DSC), and thermogravimetric analysis (TGA). The relatively low chemical reactivity of 1 toward diisocyanates was interpreted on the basis of their structural features. The phosphorus-containing polyureas showed a lower molecular weight, a lower polymer decomposition temperature, and a higher char yield than the corresponding common polyureas. Their fire-resistance was evaluated by determining the limiting oxygen index value.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pol.1984.170221158
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  • 8
    Electronic Resource
    Electronic Resource
    Phosphorus-containing polyurethanes and copolyurethanes based on 1,2-dihydroxy-1,2-bis(diethoxyphosphinyl)ethane (1984)
    New York : Wiley-Blackwell
    Journal of Polymer Science: Polymer Chemistry Edition 22 (1984), S. 891-903 
    Details
    ISSN: 0360-6376
    Keywords: Physics ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The reactions of 1,2-dihydroxy-1,2-bis(diethoxyphosphinyl)ethane (DBE) with various diisocyanates, such as tolylene diisocyanate, methylenebis(4-phenylisocyanate), and hexamethylene-1,6-diisocyanate, were studied for the synthesis of phosphorus-containing polyurethanes. In addition, DBE and ethyleneglycol or butanediol-1,4 were copolymerized with the diisocyanates. The synthesized poyurethanes were characterized by Fourier transform-infrared (FT-IR), proton nuclear magnetic resonance spectroscopy (1H-NMR), differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), and dynamic mechanical analysis (DMA). Their thermal properties were compared with those of the corresponding common polyurethanes. The fire resistance of the copolyurethanes was evaluated by determining their limiting oxygen index and smoke evolution.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/pol.1984.170220401
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  • 9
    Electronic Resource
    Electronic Resource
    High temperature laminating resins based on maleimido end-capped pyromellitimide (1988)
    New York, NY [u.a.] : Wiley-Blackwell
    Journal of Applied Polymer Science 36 (1988), S. 691-702 
    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: A novel class of bismaleimides, biscitraconimides, and bisdichloromaleimides chain-extended by pyromellitimide was prepared and characterized by infrared and proton nuclear magnetic resonance spectroscopy. These polymer precursors were prepared by reacting maleic/citraconic/dichloromaleic anhydride (1 mol) with an equimolar amount of a diamine and subsequently with pyromellitic dianhydride (0.5 mol). The tetraamic acid formed was cyclodehydrated by chemical or thermal means. The curing behavior of polymer precursors was investigated by differential thermal analysis. Bismaleimide was thermally polymerized at a relatively higher temperature than the corresponding biscitraconimide and at lower temperature than bisdichloromaleimide. The curing temperature of monomers fluctuated between 209 and 318°C. Dynamic thermogravimetric analysis of the cured aromatic resins showed that they were approximately stable up to 370°C both in nitrogen and air. Their char yield was 53-63% at 800°C under anaerobic conditions. The relative thermal stability of the cured resins, with respect the diamine utilized for imidization, was of the order p-phenylenediamine 〉 4-aminophenyl ether 〉 4,4′-diaminodiphenylmethane 〉 4,4′-diaminodiphenylsulfone 〉 hexamethylenediamine. In addition, the thermal and thermooxidative stability of polymers was ascertained by isothermal gravimetric analysis.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/app.1988.070360318
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  • 10
    Electronic Resource
    Electronic Resource
    Self-curing epoxy compounds (1990)
    New York, NY [u.a.] : Wiley-Blackwell
    Journal of Applied Polymer Science 41 (1990), S. 2613-2624 
    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: A new series including eight structurally different self-curing epoxy compounds bearing azomethine linkages were synthesized, characterized and polymerized. 4-(2,3-Epoxypropoxy)-benzaldehyde (EPB) or 2,3-epoxypropyl glyoxylate monohydrate (EPG), prepared by reacting 4-hydroxybenzaldehyde or glyoxylic acid monohydrate, respectively, with excess of epichlorohydrin in the presence of benzyltrimethylammonium bromide as catalyst, were used as starting materials. EPB or EPG reacted with an equimolar amount of a substituted aromatic amine (4-aminobenzoic acid, 5-aminoisophthalic acid, 4-aminophenol, or 1,4-phenylene-diamine) to afford the epoxy compounds. They were characterized by IR and 1H-NMR spectroscopy. Their thermal polymerization was investigated by DTA. The thermal stabilities of cured resins were evaluated by dynamic TGA and isothermal gravimetric analysis (IGA). The polymers of the epoxy compounds derived from EPB were stable up to 225-298°C in N2 and afforded anaerobic char yield of 57-62% at 800°C.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/app.1990.070411109
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