-CH₂CA(OH)CH₂NRR基を有するアゾ染料(第1報)

抄録

By the reaction of epichlorohydrin followed by diethylamine on aniline and α-naphthylamine, respectively, N-type C₆H₅NHCH₂CH(0H)CH₂N(C₂H₅)₂ (1) (yield 56.65%), by 154-5°c/2 mm, and 1-C₁₀H₇NHCH₂CH(OH)CH₂N(C₂H₅)₂ (2) yield 65.5%, bp 210°c/2 mm, were obtained. Also, by the reaction of epichlorohydrin on N-acetyl-m-aminophenol, followed by the reaction of diethylamine and hydrolysis of the product 0-type compound, m-H₂NC₆H₄OCH₂CH(OH)CH₂N(C₂H₅)₂ (3) (yield 49.5%, by 202-204°c/5 mm mp, 33-35deg;c) was obtained. A series of N-type azo dyes were synthesized by use of (1) and (2), respectively, as azo component, and various atom aticprimary amines having no carboxyl and sulf onyl group, such as p-nitroaniline, self anylamide and others, as diazo component. Also, O-type azo dyes were synthesized by use of (3) as diazo component, and dimethylaniline, β-naphthol, Naphthol AS, and 3-methyl-1-phenylpyrazolone-5 as azo components. A monoazo dye of 0-type was also prepared using (3) as azo component and Fast Red B base as diazo component; further diazotation of this dye and coupling it with dimethylaniline, Naphthol AS, etc. gave 0-type disazo dyes. The O- and N-type dyes thus obtained are soluble in dilute acetic acid, and have good dyeing property for Orlon type polyacrylonitrile fiber (Exlan L, Vonnel W and Cashmilon) with color ranges of yellow- orange- red- brown- purple. The quarternary ammonium salts of above dyes also showed similar characteristics.