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  • 2,6-bis(4-aminophenoxy)naphthalene  (2)
  • aromatic polyamides  (2)
  • 1
    Electronic Resource
    Electronic Resource
    Synthesis and properties of aromatic polyamides based on non-, methyl-, and phenyl-substituted 4,4′-bis(1,4-phenylenedioxy)dibenzoic acids (1996)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 34 (1996), S. 1433-1441 
    Details
    ISSN: 0887-624X
    Keywords: aromatic polyamides ; ether-dicarboxylic acids ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 4,4′-(1,4-Phenylenedioxy)dibenzoic acid (3), 4,4′-(2,5-tolylenedioxy)dibenzoic acid (Me-3), and 4,4′-(2,5-biphenylenedioxy)dibenzoic acid (Ph-3) were prepared by the nucleophilic substitution reaction of p-fluorobenzonitrile with hydroquinone, methylhydroquinone, and phenylhydroquinone, respectively, followed by alkaline hydrolysis. Several aromatic polyamides having inherent viscosities of 0.66-1.34 dL/g were directly prepared by a Yamazaki phosphorylation polyamidation technique from dicarboxylic acids 3, Me-3, and Ph-3, respectively, with aromatic diamines using triphenyl phosphite and pyridine as condensing agents. The solubility of methyl- or phenyl-substituted polyamides was remarkably enhanced when compared to that of nonsubstituted analogues. Most of the substituted polyamides revealed an amorphous nature and were readily soluble in a variety of organic solvents including N,N-dimethylacetamide (DMAc), N-methyl-2-pyrrolidone (NMP), N,N-dimethylformamide, dimethyl sulfoxide, and m-cresol. Transparent, flexible, and tough films of these polymers could be cast from the DMAc or NMP solutions. These films had tensile strength of 60-100 MPa, elongation to break of 6-11%, and tensile modulus of 1.68-2.25 GPa. The glass transition temperatures (Tg) of most polyamides could be determined by differential scanning calorimetry (DSC) and were in the range of 200-232°C. Thermogravimetric analyses established that these polymers were fairly stable up to 450°C, and the 10% weight loss temperatures were recorded in the range of 458-535°C in nitrogen and 468-528°C in air atmosphere. In general, the phenyl-substituted polyamides exhibited relatively higher Tg, thermal stability, and solubility. © 1996 John Wiley & Sons, Inc.
    Additional Material: 7 Ill.
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  • 2
    Electronic Resource
    Electronic Resource
    Preparation and properties of aromatic polyamides from 1,4-bis(p-carboxyphenoxy)naphthyl and aromatic diamines (1997)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 35 (1997), S. 2273-2280 
    Details
    ISSN: 0887-624X
    Keywords: 1,4-bis(p-carboxyphenoxy)naphthyl ; aromatic polyamides ; solubility ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A new aromatic dicarboxylic acid, 1,4-bis (p-carboxyphenoxy)naphthyl (3), was synthesized by the reaction of p-fluorobenzonitrile with 1,4-naphthalenediol, followed by hydrolysis. Aromatic polyamides having inherent viscosities of 1.27-2.22 dL/g were prepared by the triphenyl phosphite activated polycondensation of diacid 3 with various aromatic diamines. Most of the resulting polymers showed an amorphous nature and were readily soluble in a variety of organic solvents including N,N-dimethyl-acetamide (DMAc), N-methyl-2-pyrrolidone (NMP), and m-cresol. Transparent, tough, and flexible films of these polymers could be cast from the DMAc or NMP solutions. The cast films had tensile strengths ranging from 64-104 MPa, elongations-at-break from 6 to 10%, and initial moduli from 1.52 to 2.14 GPa. These polyamides had glass transition temperatures in the range of 195 to 240°C. Almost all polymers were thermally stable up to 400°C, with 10% weight loss being recorded above 480°C in air and nitrogen atmospheres. © 1997 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 35: 2273-2280, 1997
    Additional Material: 3 Ill.
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  • 3
    Electronic Resource
    Electronic Resource
    Synthesis and properties of aromatic polyamides derived from 2,6-bis(4-aminophenoxy)naphthalene and various aromatic dicarboxylic acids (1997)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 35 (1997), S. 2147-2156 
    Details
    ISSN: 0887-624X
    Keywords: 2,6-bis(4-aminophenoxy)naphthalene ; polyamides ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2,6-Bis(4-aminophenoxy)naphthalene (2,6-BAPON) was synthesized in two steps from the condensation of 2,6-dihydroxynaphthalene with p-chloronitrobenzene in the presence of potassium carbonate, giving 2,6-bis(4-nitrophenoxy)naphthalene, followed by hydrazine hydrate/Pd - C reduction. A series of new polyamides were synthesized by the direct polycondensation of 2,6-BAPON with various aromatic dicarboxylic acids in the N-methyl-2-pyrrolidone (NMP) solution containing dissolved metal salts such as CaCl2 or LiCl using triphenyl phosphite and pyridine as condensing agents. The polymers were obtained in quantitative yields with inherent viscosities of 0.62-2.50 dL/g. Most of the polymers were soluble in aprotic dipolar solvents such as N,N-dimethylacetamide (DMAc) and NMP, and they could be solution cast into transparent, flexible, and tough films. The casting films had yield strengths of 84-105 MPa, tensile strengths of 68-95 MPa, elongations at break of 8-36%, and tensile moduli of 1.4-2.1 GPa. The glass transition temperatures of the polyamides were in the range 155-225°C, and their 10% weight loss temperatures were above 505°C in nitrogen and above 474°C in air. © 1997 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 35: 2147-2156, 1997
    Additional Material: 2 Ill.
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  • 4
    Electronic Resource
    Electronic Resource
    New poly(amide-imide) syntheses. XXI. Synthesis and properties of aromatic poly(amide-imide)s based on 2,6-bis(4-trimellitimidophenoxy)naphthalene and aromatic diamines (1998)
    Bognor Regis [u.a.] : Wiley-Blackwell
    Journal of Polymer Science Part A: Polymer Chemistry 36 (1998), S. 919-927 
    Details
    ISSN: 0887-624X
    Keywords: poly(amide-imide)s ; direct polycondensation ; 2,6-bis(4-aminophenoxy)naphthalene ; 2,6-bis(4-trimellitimidophenoxy)naphthalene ; Chemistry ; Polymer and Materials Science
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A novel polymer-forming diimide-diacid, 2,6-bis(4-trimellitimidophenoxy)naphthalene, was prepared by the condensation reaction of 2,6-bis(4-aminophenoxy)naphthalene with trimellitic anhydride (TMA). A series of novel aromatic poly(amide-imide)s containing 2,6-bis(phenoxy)naphthalene units were prepared by the direct polycondensation of the diimide-diacid with various aromatic diamines using triphenyl phosphite (TPP) in N-methyl-2-pyrrolidone (NMP)/pyridine solution containing dissolved calcium chloride. Thirteen of the obtained polymers had inherent viscosities above 1.01 dL/g and up to 2.30 dL/g. Most of polymers were soluble in polar solvents such as DMAc and could be cast from their DMAc solutions into transparent, flexible, and tough films. These films had tensile strengths of 79-117 MPa, elongation-at-break of 7-61%, and initial moduli of 2.2-3.0 GPa. The wide-angle X-ray diffraction revealed that some polymers are partially crystalline. The glass transition temperatures of some polymers could be determined with the help of differential scanning calorimetry (DSC) traces, which were recorded in the range 232-300°C. All the poly(amide-imide)s exhibited no appreciable decomposition below 450°C, and their 10% weight loss temperatures were recorded in the range 511-577°C in nitrogen and 497-601°C in air. © 1998 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 36: 919-927, 1998
    Additional Material: 1 Ill.
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