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
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[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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