Journal of the Japan Society of Colour Material

[title in Japanese]

[in Japanese]

1971 Volume 44 Issue 7 Pages 303
Published: July 30, 1971
Released on J-STAGE: November 20, 2012

DOIhttps://doi.org/10.4011/shikizai1937.44.303

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Studies on Red Mono Azo Pigment. I

Studies on Series of Pigments Containing 4-Methyl-3-Amino Benzoic Acid in Diazo Components

Atsuto ABE, Hiroshi OZOE, Hidehiko SAKAI, Masanori AOYAMA

1971 Volume 44 Issue 7 Pages 304-315
Published: July 30, 1971
Released on J-STAGE: November 20, 2012

DOIhttps://doi.org/10.4011/shikizai1937.44.304

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Authors synthesized red mono azo pigments shown in the general formula :
X, CH₃ - N = N - HO CONH-Ar wherein X represents hydrogen atom, chlorine atom, methyl group, methoxy group or nitro group and Ar represents benzene residue (naphthol AS), 4-chloro benzene residue (naphthol AS-E), 2-methyl benzene residue (naphthol AS-D), 4-methoxy benzene residue (naphthol AS-OL), 4-methoxy benzene residue (naphthol AS-RL), 2, 4-dimethoxy-5-chloro benzene residue (naphthol AS-ITR), 2-5-dimethoxy -4-chloro benzene residue (naphthol AS-LC), α-naphthalene residue (naphthol AS-BO), β-naphthalene residue (naphthol AS-SW), according to the following process of preparing reactions :
CH₃ COOH nitration CH₃ COOH NO₂ reduction CH₃ COOH NH₂·HCI diazotization CH₃ COOH N=N-CI nitration CH₃ COOH N=N- HO CONH-Ar carboxylic acid chlorination CH₃ COCI N=N- HO CONH-Ar condensation X HNOC CH₃ -N=N- HO CONH-Ar
Then, the anthours studied on the effect of the substituents of diazo or coupling component on the pigment properties. As a result of the study, these pigments have a dominant wave length at 602. 4nm-670 nm and further -492.5 nm.
The pigments containing naphthol AS-E and naphthol AS as the coupling component gave generally yellowish-red shade, and the ones containing naphthol AS-OL, naphthol AS-ITR and naphthol AS-LC generally bluish-red shade. No clear correlation between the kinds or properties of substituents and color shade was found however.

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Studies on quinophthalone pigments

Masayuki MIYATAKE, Shigeyuki EHASHI

1971 Volume 44 Issue 7 Pages 316-324
Published: July 30, 1971
Released on J-STAGE: November 20, 2012

DOIhttps://doi.org/10.4011/shikizai1937.44.316

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The Quinoline Yellow SS prepared by condensation of phthalic anhydride with quinaldine is bright greenish yellow in hue, and used as the spirit soluble dye, but poor in the resistance to the light.
Recently, it was reported that the quinophthalones obtained from substituted and unsubstituted quinaldines and tetrahalogenophthalic anhydrides were bright yellow in shade, excellent in the resistance to the light, but not good enough in the resistance to the aromatic solvents.
Therefore, the authors tried to improve the resistance to the organic solvents by dimerization of quinophthalone, namely the authors synthesized several new bisquinophthalones by condensation of phthalic anhydride or tetrahalogenophthalic anhydrides with 6, 6'-biquinaldines which were obtained from benzidines and crotonaldehyde in the Doebner-Miller synthesis. The new twelve bisquinophthalone pigments thus prepared are shown by the following formula;
Z-Z-Z-Z-OC-OC-HC-N-X-Y-X-Y-N-CH-OC-OC-Z-Z-Z-Z
wherein X represents hydrogen atom or chlorine atom, Y represents hydrogen atom, chlorine atom or methylgroup, and Z represents hydrogen atom, chlorine atom or bromine atom.
The authors tested the properties of those pigments, and obtained such a result that the pigments prepared from 6, 6'-biquinaldines and phthalic anbydride were bright yellow in hue, but poor in the resistance to the light and the organic solvents of high boiling point.
The polyhalogenobisquinophthalones obtained from 6, 6'-biquinaldines and tetrahalogenophthalic anhydrides gave bright yellow shade, excellent resistance to light and organic solvents, except for the pigment prepared from 5, 5', 8, 8'-tetrachlor6, 6'-biquinaldine and tetrahalogenophthalic anhydride.
The authors found that the effect of dimerization of quinophthalone was remarkable to improve the resistance to the organic solvents.

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[title in Japanese]

[in Japanese]

1971 Volume 44 Issue 7 Pages 331-350
Published: July 30, 1971
Released on J-STAGE: November 20, 2012

DOIhttps://doi.org/10.4011/shikizai1937.44.331

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