1,4,5,8-naphthalene tetracarboxylic dianhydride

NaOH-catalyzed resole resin, 409 Naphthalene diisocyanate (NDI), 201 Naphthalene tetracarboxylic dianhydride (NDTA), 282... 

Perinones are structurally similar to perylenes being made by condensing naphthalene tetracarboxylic dianhydride with amines, but in this case 1,2-diamines, e.g. Cl Pigment Orange 43 (2.71), or its cis isomer. The isomers can be separated by fractionation of their salts. They offer orange to bordeaux shades with similar properties to perylenes, but are less commercially important. 

The proposed reduction process for 1,4,5,8-naphthalene tetracarboxylic dianhydride (NTDA)-, PMDA-, and BPDA-polyimides involves two sequential one-electron transfers to generate the radical-anion and dianion states respectively. In the case of BPDA-polymers, the formation of a diradical-dianion on the second reduction might be more energetically favored over the... 

NTCDA naphthalene tetracarboxylic dianhydride PTCDA perylene tetracarboxylic dianhydride... 

Figure 14-20. Molecular structure of naphthalene tetracarboxylic dianhydride (NTCDA) and perylene tetracarboxylic dianhydride (PTCDA).

Another interesting feature in the data given in Table 14-3 is the different mobility reported for NTCDA (naphthalene tetracarboxylic dianhydride) and PTCDA (perylene tetracarboxylic dianhydride). These two compounds present very similar molecular formulae (Fig. 14-20), but differ by their crystal packing... 

All these dianhydrides should have a very high reactivity, because of the lower values of lumo for both the dianhydride and the monoamide. In fact, hexafluoroisopropyliden 4,4 -diphthalic anhydride should be only slightly less reactive than benzophenone tetracarboxylic dianhydride, and 2,3,6,7-naphthalene tetracarboxylic dianhydride should be very similar to biphenyl dianhydride. But if the reaction is controlled by the monoamide, as we have postulated, the most reactive dianhydride should be 1,4,5,8-naphthalene tetracarboxylic dianhydride, because lumo is almost the same than for pyromellitic dianhydride, but lumo monoamide is lower than lumo monoamide of the pyromellitic (—2.33 versus — 2.18eV). 

E.g. polycondensates from 1,4,5,8-Naphthalene tetracarboxylic dianhydride, 2,2 -Benzidinesulfonic acid and Bis[4-(3-aminophenoxy)-phenyl]sulfone [86, 87],... 

Suda et al. [288] reported the synthesis and characterization of a series of sulfonated star-hb polyimides (S-hb-Pls) without any crosslinking for use as proton exchange membranes. Sulfonated anhydride-terminated polyimides with different molecular weights (M v = 59,000, 200,000 and 300,000 Da) based on monomer combination 1,4,5,8-naphthalene tetracarboxylic dianhydride/4,4 -diaminobiphenyl 2,2 -disulfonic acid (NTDA/BDSA) were synthesized using different molar ratios of BDSA NTDA. The amine-terminated hb-Pl based on monomer combination 4,4-(hexafluoroisopropylidene)diphthalic anhydride/tris(4-aminophenyl)amine (6EDA/TAPA) was also prepared. Scheme 33 shows the monomer combinations used for the preparation of (S-hb-Pl). 

Zhang, Y., and Litt, M. H. (1999). Polyimides based on naphthalene tetracarboxylic dianhydride and benzidinedisulfonic acid. ACS Polym. Preprints 40(2), 480. 

Abstract Three series of new polyimides were prepared by condensation of imidazole-blocked 2,5-bis(n-alkoxymethyl)-1,4-benzene diisocyanates with pyromellitic dianhydride (PMDA), benzophenone tetracarboxylic dianhydride (BPDA), and naphthalene tetracarboxylic dianhydride (NTDA), respectively. After the polymers obtained were spectroscopically characterized, their solubilities, thermal properties and crystalline structures were measured and discussed. It was found that structures and properties of the polyimides having regularly substituted n-alkoxymethyKn-CHjOC Hj j, m=4,6,8) side branches are governed not only by side chain length, but also by main chain rigidity. 

Direct polymerization from sulfonated monomers is the most widely used method for the synthesis of the SPIs. The synthesis is usually performed by polycondensation reaction of sulfonated diamine monomers with tetracarboxylic dianhydride monomers in m-cresol in the presence of triethyl amine (EtjN) and benzoic acid at around 180°C [4,7,10,11,13,28-34]. Sulfonated diamines are inner salts that are formed due to the interaction of the sulfonic add groups and the basic amino groups, and the function of the EtsN is to liberate the protonated amino groups of sulfonated diamines for polymerization with the 1,4,5,8-naphthalene tetracarboxylic dianhydride (NTDA),... 

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