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  • 1
    Electronic Resource
    Electronic Resource
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 32 (1994), S. 1799-1806 
    ISSN: 0887-624X
    Keywords: cyano-substituted polymer precursors ; diamide ; diimide ; maleimide ; crosslinked polymers ; heat-resistant resins ; 4-aminoacetophenone ; malononitrile ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A novel class of polymer precursors of the general formula, where A is an aromatic structure bearing amide or imide linkages, were synthesized. More particularly, 4-aminoacetophenone was condensed with malononitrile to afford 4-amino-α-methyl-β,β′-dicyanostyrene (1). The condensation of the latter with half molar amount of terephthaloyl dichloride, pyromellitic dianhydride, or benzophenone tetracarboxylic dianhydride yielded the polymer precursors. In addition, compound 1 was condensed with an equimolar amount of maleic anhydride to afford the corresponding maleimide. The monomers were characterized by elemental analyses, FT-IR, 1H-NMR, and DTA. Crosslinked resins were obtained upon curing the monomers at 300°C for 72 h. They were stable up to 381-422°C in N2 or air and afforded anaerobic char yields of 64-68% at 800°C. © 1994 John Wiley & Sons, Inc.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 31 (1993), S. 1771-1778 
    ISSN: 0887-624X
    Keywords: heat-resistant resins ; cyano-substituted polymer precursors ; crosslinked polymers ; 4-hydroxy-β,β′-dicyanostyrene ; 3-amino-β,β′-dicyanostyrene ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Certain polymer precursors of the general formula: where A is an aromatic structure bearing ester, amide, azomethine, or imide linkages were synthesized. Particularly, 4-hydroxybenzaldehyde was condensed with malonitrile to afford 4-hydroxy-β,β′-dicyanostyrene which reacted with a half molar amount of terephthaloyl dichloride in the presence of an acid acceptor. In addition, 3-nitrobenzaldehyde was condensed with malonitrile to yield 3-nitro-β,β′-dicyanostyrene that was catalytically hydrogenated to the corresponding amine. The latter reacted with a half molar amount of terephthaloyl dichloride, terephthaldehyde, pyromellitic dianhydride, or benzophenone tetracarboxylic dianhydride. The polymer precursors were characterized by elemental analyses as well as IR and 1H-NMR spectroscopy. Their curing behavior was investigated by DTA. Crosslinked polymers were obtained by curing the monomers at 300°C for 24 h. They were stable up to 407-437°C in N2 and afforded an anaerobic char yield of 65-50% at 800°C. The thermal stability of resins was correlated with their chemical structures. © 1993 John Wiley & Sons, Inc.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    New York : Wiley-Blackwell
    Journal of Polymer Science: Polymer Chemistry Edition 22 (1984), S. 1065-1076 
    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
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  • 4
    Electronic Resource
    Electronic Resource
    New York : Wiley-Blackwell
    Journal of Polymer Science: Polymer Chemistry Edition 22 (1984), S. 3535-3548 
    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
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  • 5
    Electronic Resource
    Electronic Resource
    New York : Wiley-Blackwell
    Journal of Polymer Science: Polymer Chemistry Edition 22 (1984), S. 891-903 
    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
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  • 6
    Electronic Resource
    Electronic Resource
    New York : Wiley-Blackwell
    Journal of Polymer Science: Polymer Chemistry Edition 22 (1984), S. 1717-1732 
    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
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  • 7
    Electronic Resource
    Electronic Resource
    New York : Wiley-Blackwell
    Journal of Polymer Science: Polymer Chemistry Edition 22 (1984), S. 3423-3437 
    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
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