Naphthalene-1,4,5,8-tetracarboxylic acid dianhydride

Dibenzothiophene acts as a 7r-electron donor and readily forms complexes with known electron acceptors. In such cases the electronic spectrum of a solution of the two compounds shows a new absorption band, usually in the visible region. The order of donor strengths of several o,o -bridged biphenyls has been estimated from their respective charge-transfer spectra and found to be carbazole > fluorene > dibenzothiophene >dibenzofuran. Dibenzothiophene forms complexes with tetracy-anoethylene, various polynitro derivatives of fluorenone, > naphthalene-1,4,5,8-tetracarboxylic acid dianhydride, and tetra-methylmic acid. ... 

Pigment Orange 43 [4424-06-0] 71105 Perinone condensation of naphthalene-1,4,5,8-tetracarboxylic acid dianhydride with o-phenylenediamine, and separation of trans isomer... 

The fact that all bis(naphthalic anhydrides) display lower reactivity than naphthalene-1,4,5,8-tetracarboxylic acid dianhydride, has predetermined an expedient synthesis of their polyheteroarylenes. It involves catalytic processes which find wide application in polycondensation and polycyclocondensation reactions [154, 155]. 

In contrast to a more rigid polymer derived from naphthalene-1,4,5,8-tetracarboxylic acid dianhydride precipitating from m-cresol at this concentration, the obtained polyimides retained solubility in m-cresol up to a concentra-... 

It was shown that soluble PPI can be synthesised directly from DPTA and series of aromatic diamines containing flexible units, namely 2,2-bis[4-(3-aminophenoxy)phenyl]propane and 2,2-bis[4-(3-aminophenoxy)phenyl]hexafluoro-propane were reported (Scheme 1.2) [5]. Previously these diamines were used successfully in the synthesis of soluble polyimides starting from naphthalene-1,4,5,8-tetracarboxylic acid dianhydride [14]. 

Polyimides Based on Naphthalene-1,4,5,8-Tetracarboxylic Acid Dianhydride... 

Not all attempts at formations of ladder polymers yielded completely cyclized fused ring structures. For instance, an attempt to form a polymer from tetraaminonaphthalene with naphthalene tetracarboxylic acid dianhydride failed to yield complete cyclizations [222]. 

The synthesis of BBL (poly benzimidazobenzophen-anthroline) from 1,2,4,5-tetraaminobenzeneand 1,4,5,8-naphthalene tetracarboxylic acid dianhydride (Arnold and vanDeussen [16,17]) represented a definite step forward (Scheme 4). BBL is to some extent soluble, e.g., in strongly acidic media such as sulfuric acid or meth-anesulfonic acid and can be worked into transparent films and layers. Jenekhe et al. [18] published a method... 

Perylene pigments include the dianhydride and diimide of perylene tetracarboxylic acid along with derivatives of the diimide while perinone pigments are derived from naphthalene tetracarboxylic acid. 

A new quality in ladder polymer synthesis via multifunctional polycondensation was reached in the late 1960s when poly(benzimidazobenzo-phenanthroline) (BBL) 12 was prepared by Arnold and van Deusen [21 -24]. The polymer was synthesized from naphthalene-l,4,5,8-tetracarboxylic acid dianhydride (11) and 1,2,4,5-tetraaminobenzene (la) in strong acidic media (polyphosphoric acid, sulfuric acid). BBL is completely soluble in concentratal sulfuric acid or methanesulfonic add and is processible into durable films and... 

In contrast, polynaphthoylenebenziniidazote based on 2,2-bis(3,4-diaminophenyl) hexafluoropropane are soluble not only in H2SO4, m-cresol and a tetrachloroethane-phenol mixture (3 1) (this is characteristic for polymers derived from bis(o-phenylenediamine) and naphthalene-l,4,5,8-tetracarboxylic acid dianhydride [183, 184]) but also in N-MP (N-methylpyrolidane). An enhanced solubility of polynaphthoyleiKbenzimidazoles of this series is explained not only by the introduction of a hinge group between naphthalic anhydride moieties, but also by low viscosity characteristics of the systems caused by low basicity of 2,2-bis(3,4-diaminophenyl)hexafluoropropane [185],... 

Naphthalene-l, 4,5,8-tetracarboxylic acid dianhydride 118, 137, 138, 140, 146, 147 2,6-Naphthalenedicarboxylic acid 196 Nonlinear optical polymers 36... 

Another class of polyimides that are characterised by a higher chain flexibility, when compared to PPI, are based on naphthalene-l,4,5,8-tetracarboxylic acid dianhydride (DNTA). These polymers are of considerable interest due to their high heat resistance and thermal stability and due to easy accessibility of the starting monomers. DNTA is a widely available dianhydride showing the highest electrophilic reactivity among bisfnaphthalene-tetracarboxylic anhydrides [18, 19]. 

PA-66 (50 parts)/PPE (50 parts)/SEBS (5 parts)/ 1,2,3,4-cyclopentane tetracarboxylic acid (0.5 parts) TSE at 315-321 °C/mechanical properties/PPE preextruded with acid/also used 1,4,5,8-naphthalene tetracarboxylic acid, pyromellitic dianhydride, tetrabromophthalic anhydride Grant and Jalbert 1989... 

Several methods have been reported for the monofunctionaUzation of PDI [6] including one-pot imidization (route A) or a base-promoted coupling reaction between naphthalene monoimide derivatives (route B) [7], as shown in Scheme 2. We found the one-pot imidizatitMi reaction (route A) to be more practical than route B route B consisted of five steps and the open-form product 6b was labile under the basic reaction conditions required to produce the closed product 6a. The one-pot imidization, route A, was simple and 3 could easily be recovered via column chromatography because the use of an excess amount of 3 was necessary. Concerning the solubility and reactivity of perylene tetracarboxylic acid dianhydride (PDA) 4, the imidization of 4 was, first, carried out with 2,6-ditsopropylaniline (5) in imidazole then 3 in propionic acid solution was added to produce the closed product PDI 6a. 

Polyimides are also obtained in one step in the reaction of diisocyanates with tetracarboxylic acid dianhydrides. As an example, BTDA is reacted with a mixture of 2,4-TDI and MDI in DMF (93). This copolyimide, PI 2080, is used as a high temperature fiber and it is also sinter molded into solid shapes with exceptional mechanical properties. From PMDI and benzophenone-tetracarboxylic acid dianhydride polyimide foams with outstanding thermal properties and flame resistance are produced (94). Pol5fimides derived from p-phenylene diisocyanate (PPDI) or naphthalene diisocyanate (NDI) and pyromellitic dianhydride or BTDA are also synthesized using DMAc as solvent (95). 

The primary starting material for the synthesis of perylene tetracarboxylic acid pigments is the dianhydride 71. It is prepared by fusing 1,8-naphthalene dicar-boxylic acid imide (naphthalic acid imide 69) with caustic alkali, for instance in sodium hydroxide/potassium hydroxide/sodium acetate at 190 to 220°C, followed by air oxidation of the molten reaction mixture or of the aqueous hydrolysate. The reaction initially affords the bisimide (peryldiimide) 70, which is subsequently hydrolyzed with concentrated sulfuric acid at 220°C to form the dianhydride ... 

Table 23 demonstrates the mesogenicity of polymers containing biphenylene-S j -tetracarboxylic imide. A comparison of series 9 and 10 in the table shows that replacement of pyromellitic dianhydride with BPTA in a copolymer with two moles of m-aminophenol and an aromatic diacid does not lead to mesogenic polymers. The assignment of an MI score of 4 compared to 2 for pyromellitic anhydride does however raise the MI as far as the borderline condition of MI=9.5 when 2,6-naphthalene dicarboxylic acid is the co-monomer. 

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

Abbreviations CBZ, carbazole PNVC, poly(Af-vinylcarbazole) PhAn, phthalic anhydride TMA, trimellitic acid anhydride PMDA, pyromellitic dianhydride NTDA naphthalene tetracarbot lic dianhydride BTDA benzophe-none tetracarboxylic dianhydride. 

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. 

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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