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Volumn 37, Issue 4, 2004, Pages 1289-1296

Reevaluation of Tetrahydrophthalic Anhydride as an End Cap for Improved Oxidation Resistance in Addition Polyimides

Author keywords

[No Author keywords available]

Indexed keywords

DIELS-ALDER REACTIONS; THERMOOXIDATIVE STABILITY;

EID: 1642308866     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma0353078     Document Type: Article
Times cited : (7)

References (30)
  • 8
    • 1642275247 scopus 로고    scopus 로고
    • U.S. Patent Number 6,303, 744, Oct 16, 2001
    • Meador, M. A. B.; Frimer, A. A. U.S. Patent Number 6,303, 744, Oct 16, 2001.
    • Meador, M.A.B.1    Frimer, A.A.2
  • 9
    • 1642351706 scopus 로고    scopus 로고
    • NASA Glenn Research Center, personal communication, Aug 16
    • Alston, W. B. NASA Glenn Research Center, personal communication, Aug 16, 2002.
    • (2002)
    • Alston, W.B.1
  • 16
    • 0141856231 scopus 로고    scopus 로고
    • Similar NMR data have recently been reported for the tridecafluorohexylphenyl analogue. See the Supporting Information for compound 30 in: Werner, S.; Curran, D. P. Org. Lett. 2003, 5, 3293-3296.
    • (2003) Org. Lett. , vol.5 , pp. 3293-3296
    • Werner, S.1    Curran, D.P.2
  • 17
    • 1642363104 scopus 로고    scopus 로고
    • compound 13 therein
    • 1H NMR data for 3-phenylphthalic anhydride (4-phenylisobenzofuran-1,3-di-one). See: Brown, R. F. C.; Choi, N.; Eastwood, N. C. Aust. J. Chem. 2000, 53, 161-166 (compound 13 therein).
    • (2000) Aust. J. Chem. , vol.53 , pp. 161-166
    • Brown, R.F.C.1    Choi, N.2    Eastwood, N.C.3
  • 18
    • 1642381083 scopus 로고    scopus 로고
    • U.S. Patent Number 6,274,699, Aug 14, 2001
    • Meador, M. A. B. U.S. Patent Number 6,274,699, Aug 14, 2001.
    • Meador, M.A.B.1
  • 20
    • 1642387551 scopus 로고    scopus 로고
    • We thank Dr. Hugo E. Gottlieb (Magnetic Resonance Laboratory, Bar Ilan University) for this suggestion
    • We thank Dr. Hugo E. Gottlieb (Magnetic Resonance Laboratory, Bar Ilan University) for this suggestion.
  • 21
    • 84862053204 scopus 로고    scopus 로고
    • 1H NMR calculations
    • 1H NMR calculations.
  • 25
    • 0343715766 scopus 로고
    • (c) Crowshaw, K.; Newstead, R. C.; Roger, N. A. J. Tetrahedron Lett. 1964, 5, 2307-2311-see Frimer, A. A. In The Chemistry of Enones, Part 2; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1989; pp 781-921, 837-838.
    • (1964) J. Tetrahedron Lett. , vol.5 , pp. 2307-2311
    • Crowshaw, K.1    Newstead, R.C.2    Roger, N.A.3
  • 26
    • 0002116819 scopus 로고
    • Patai, S., Rappoport, Z., Eds.; Wiley: Chichester
    • (c) Crowshaw, K.; Newstead, R. C.; Roger, N. A. J. Tetrahedron Lett. 1964, 5, 2307-2311-see Frimer, A. A. In The Chemistry of Enones, Part 2; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1989; pp 781-921, 837-838.
    • (1989) The Chemistry of Enones, Part 2 , pp. 781-921
    • Frimer, A.A.1
  • 30
    • 1642343582 scopus 로고    scopus 로고
    • note
    • 14 to be 80°C at 8 mm. This corresponds (nomograph) to a boiling point of ca. 220°C at 760 mm. The boiling point of commercial (Aldrich) trans,trans-1,4-phenyl-1,3-butadiene (8f) is 350°C. The TGA of the 2:1 mixture of 8f and MDA heated to 204°C shows a Td at 239°C (corresponding to imidization) and 352°C (corresponding to retro-Diels-Alder), with onset in both cases ca. 20°C earlier. DSC confirms these transitions.


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