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Quinophthalone compound

A compound, quinophthalone technology, applied in the field of new quinophthalone compounds, can solve the problems of undisclosed compounds, etc., and achieve the effects of excellent tinting strength, excellent brightness and tinting power, and good brightness

Active Publication Date: 2019-09-27
DIC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, Patent Documents 1, 2 and 3 do not disclose the compound of the present invention represented by the following formula (1):

Method used

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  • Quinophthalone compound
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  • Quinophthalone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0091] Hereinafter, although this invention is demonstrated based on an Example, this invention is not limited to these Examples. Wherein, in Examples and Comparative Examples, unless otherwise specified, "parts" and "%" are mass basis.

Synthetic example 1

[0094] Add 30.4g (114mmol) of 4,4'-methylenebis(2-chloroaniline), 56.1g (228mmol) of tetrachloro-p-benzoquinone, 29.5mL of concentrated hydrochloric acid, and 147mL of n-butanol in the flask, and stir at 95°C 30 minutes. To this mixture, 19.2 g (274 mmol) of crotonaldehyde was added dropwise, followed by further stirring for 1 hour. The temperature was lowered to 80°C, and 15.5 g (114 mmol) of zinc chloride was added in small amounts at a time, then 100 mL of THF was added, and the mixture was kept at 80°C and stirred for 1 hour. After cooling to room temperature, place it in an ice bath, and recover the black powder by filtration under reduced pressure. The obtained black powder was washed with 500 mL of ethanol, and the black powder was recovered by filtration under reduced pressure again. Further, the obtained black powder was transferred into a flask, 200 mL of ethanol and 400 mL of 10% aqueous sodium hydroxide solution were added, and stirred at 80° C. for 1 hour. The ...

Synthetic example 2

[0102] 4.15 g (11.3 mmol) of the intermediate (A) obtained in Synthesis Example 1 and 7.55 mL of concentrated sulfuric acid were added to the flask, and stirred at 45° C. for 20 minutes. Then, 1.62 mL of fuming nitric acid was added dropwise, and the temperature was maintained and stirring was continued for 1 hour. After standing to cool, slowly inject 250mL of ice water into the system. Further, the pH was adjusted to 8-9 with 10 wt% sodium hydroxide aqueous solution. The precipitated powder was recovered by filtration under reduced pressure, and washed with 200 mL of distilled water and 100 mL of ethanol to obtain 5.13 g (11.2 mmol) of an intermediate (B) as a yellow-orange powder. (Yield: 99%)

[0103] 1 H-NMR (CDCl 3 )δppm: 2.86(s, 6H), 4.27(s, 2H), 7.56(d, J=8.8Hz, 2H), 7.62(s, 2H), 8.08(d, J=8.8Hz, 2H)

[0104] 13 C-NMR (CDCl 3 )δppm: 25.7, 32.4, 119.9, 125.6, 127.5, 130.1, 131.1, 137.3, 143.1, 145.9, 162.2

[0105] FT-IR cm -1 :3465,1604,1530,1487,1362

[0106...

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Abstract

The present invention addresses the problem of providing a novel yellow pigment having excellent brightness and tinctorial strength. The problem is solved by providing a quinophthalone compound represented by formula (1) (in formula (1), X1-X16 are, each independently, a hydrogen atom or a halogen atom, Y is a hydrogen atom or a halogen atom, and Z is a lower alkylene group). Also provided are: a colorant containing the quinophthalone compound represented by formula (1); and a coloring composition containing the colorant.

Description

technical field [0001] The present invention relates to novel quinophthalone compounds. Background technique [0002] Patent Documents 1 and 2 disclose bisquinophthalone compounds having a certain structure. In addition, Patent Document 3 discloses a quinophthalone compound having a certain structure. However, Patent Documents 1, 2 and 3 do not disclose the compound of the present invention represented by the following formula (1). [0003] Patent Document 1: Japanese Patent Publication No. 48-32765 [0004] Patent Document 2: International Publication No. 2013 / 098836 Pamphlet [0005] Patent Document 3: Japanese Patent Laid-Open No. 53-228 Contents of the invention [0006] The problem to be solved by the invention [0007] At present, coloring compositions are used in various fields, and specific applications include printing inks, paints, colorants for resins, colorants for fibers, color materials for information recording (color filters, colorants, toners, color ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B25/00G02B5/20
CPCC09B25/00G02B5/223C07D401/14C07D401/04
Inventor 重广龙矢近藤仁安井健悟
Owner DIC CORP