4,4 -Diaminodiphenyl ether

Polyimides for use ia molded products and high temperature films can be produced by the reaction of pyromelHtic dianhydride [89-32-7] and 4,4 -diaminodiphenyl ether [13174-32-8] ia DMAC to form a polyamide that can be converted iato a polyimide (13). DMAC can also be used as a spinning solvent for polyimides. AdditionaUy, polymers containing over 50% vinyHdene chloride are soluble up to 20% at elevated temperatures ia DMAC. Such solutions are useful ia preparing fibers (14). 

Technora. In 1985, Teijin Ltd. introduced Technora fiber, previously known as HM-50, into the high performance fiber market. Technora is based on the 1 1 copolyterephthalamide of 3,4 -diaminodiphenyl ether and/ -phenylenediamine (8). Technora is a whoUy aromatic copolyamide of PPT, modified with a crankshaft-shaped comonomer, which results in the formation of isotropic solutions that then become anisotropic during the shear alignment during spinning. The polymer is synthesized by the low temperature polymerization of/ -phenylenediamine, 3,4 -diaminophenyl ether, and terephthaloyl chloride in an amide solvent containing a small amount of an alkaU salt. Calcium chloride or lithium chloride is used as the alkaU salt. The solvents used are hexamethylphosphoramide (HMPA), A/-methyl-2-pyrrohdinone (NMP), and dimethyl acetamide (DMAc). The stmcture of Technora is as follows ... 

The chemical production of aminophenols via the reduction of nitrobenzene occurs in two stages. Nitrobenzene [98-95-3] is first selectively reduced with hydrogen in the presence of Raney copper to phenylhydroxylamine in an organic solvent such as 2-propanol (37). With the addition of dilute sulfuric acid, nucleophilic attack by water on the aromatic ring of /V-phenylhydroxylamine [100-65-2] takes place to form 2- and 4-aminophenol. The by-product, 4,4 -diaminodiphenyl ether [13174-32-8] presumably arises in a similar manner from attack on the ring by a molecule of 4-aminophenol (38,39). Aniline [62-53-3] is produced via further reduction (40,41). 

Phenothiophosphine ring-containing polyamides and polyesters were also prepared by the polycondensation of 2,8-bischloroformyl-lO-phenylphenothiophos-phine 5,5, 10-trioxide with aromatic diamines such as 4,4 -diaminodiphenyl ether and 4,4 -diaminodiphenyl-methane, and bisphenols such as 4,4 -dihydroxybiphe-nyl and 4,4 -dihydroxydiphenylmethane, respectively [159]. These polymers are soluble in polar aprotic solvents and also exhibit good heat and fire resistance. Phosphorus containing high performance polymers are shown in Table 6. 

Polyimide-clay nanocomposites constitute another example of the synthesis of nanocomposite from polymer solution [70-76]. Polyimide-clay nanocomposite films were produced via polymerization of 4,4 -diaminodiphenyl ether and pyromellitic dianhydride in dimethylacetamide (DMAC) solvent, followed by mixing of the poly(amic acid) solution with organoclay dispersed in DMAC. Synthetic mica and MMT produced primarily exfoliated nanocomposites, while saponite and hectorite led to only monolayer intercalation in the clay galleries [71]. Dramatic improvements in barrier properties, thermal stability, and modulus were observed for these nanocomposites. Polyimide-clay nanocomposites containing only a small fraction of clay exhibited a several-fold reduction in the... 

See also 3,4 -Diaminodiphenyl ether (3,4 ODA) ODA/PPTA fibers Polyfp-phenylene terephthalamide) (PPTA) commercial process for, 19 721-723 wet spinning of, 19 725 Copolyfp-phenylene sulfide sulfone/ ketone) s, 23 710... 

Diaminodiphenyl ether (3,4 ODA), 19 715. See also Copoly(p-phenylene/ 3,4 -diphenyl ether terephthalamide) (ODA/PPTA)... 

Hi-Blen pyromellitic anhydride and 4,4-diaminodiphenyl ether ABS polymers Japanese Geon... 

The mononitrosubstitution reaction of TNB was used to prepare new aryloxy-substituted dinitro compounds [22, 23], which were converted to the corresponding aryloxy-substituted diamines. The simplest dinitrocompound and diamine obtained are 3,5-dinitrodiphenyl ether and 3,5-diaminodiphenyl ether [21-23] (Scheme 4.8). 

Properties of the polyimides based on 3,5-diaminodiphenyl ether and l-amino-3-phenoxy-5-(4-aminophenoxy)-benzene are given in Table 5.4. Comparison of the polyimides obtained using different methods does not permit a conclusion to be reached as to which method is preferable - in almost all cases high molecular weight polyimides were obtained. 

Polymers obtained using 3,5-diaminodiphenyl ether may be considered as m-phenylenediamine-based polyimides containing phenoxy side groups. A comparison of these two polymer group properties has demonstrated that introduction of phenoxy substituents leads to an increase of polymer solubility and decrease of Tg indicating that phenoxy side groups behave as chemical plasticisers this conclusion is an agreement with the literature [5, 27-31]. 

P, pyromellitic dianhydride B, 3,3, 4,4 -benzophenone tetracarboxylic dianhydride 3,5-DAB, 3,5-diaminoben benzophenone 4-MPD, 4-methoxy-m-phenylene diamine 4,4 -DDE, 4,4 -diaminodiphenyl ether 4,4 -DDM, -h The figure in parenthesis is the number of water molecules estimated to be associated with iho corresponding polar gr... 

Heat-resistant polyamide membranes containing pendant sulfonamide groups were also fabricated 91 93). Thus the membrane prepared from 2,2 -disulfonamide-4,4 -diaminodiphenyl ether-isophthaloyl chloride copolymer 34 gave the water permeation rate of 1700 1/m2 day and salt rejection of 65 %. The film with 50 p... 

Pyrazinetetracarboxylic acid forms a dianhydride on treatment with acetic anhydride,234 which is useful in the preparation of polyamides and polyimides.235-236 For example, polymeric material is obtained by reaction of the dianhydride with 4,4 -diaminodiphenyl ether. 

An approach that has been used for the synthesis of unsubstituted phenoxazine in 32% yield involves the condensation of o-nitrochloro-benzene with o-nitrophenol, followed by reduction and ring closure of the 2,2 -diaminodiphenyl ether (8).28,29... 

SYNS p-AMINOPHENYL ETHER 4-AMINOPHENYL ETHER BIS(p-AMINOPHENYL)ETHER BIS(4-AMINOPHENYL)ETHER DADPE 4,4 -DIAMINO-BIPHENYLOXIDE DIAMINODIPHENYL ETHER p,p -DIAMINODIPHENYL ETHER 4,4-DIAMINODI-PHENYL ETHER 4,4 -DIAMINODIPHENYL OXIDE 4,4 -DIAMINOPHENYL ETHER NCI-C50146 OXYBIS(4-AMINOBENZENE) p,p -OXYBIS(ANILINE)... 

Khoee S, Zamani S (2007) Synthesis, characterization and fluorimetric studies of novel photoactive poly(amide-imide) from anthracene 9-carboxaldehyde and 4,40-diaminodiphenyl ether by microwave irradiation. Eur Polym J 43 2096-2110... 

Tetracarboxypyrazine treated with acetic anhydride gave tetracarboxypyrazine dianhydride (1291, 1342). This condensed with p,p -diaminodiphenyl ether to give polyimides (18) which could be thermally processed at 40-280° in vacuo to give films having high thermal stability (1291, 1343). The preparation of polymers (resistant to thermal degradation) from tetracarboxypyrazine dianhydride and tetraaminopyrazine in polyphosphoric acid at elevated temperatures has been described (1180). 

---