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Compounds for Dyes

A compound and composition technology, applied in the direction of azo dyes, organic dyes, coumarin dyes, etc., to achieve the effect of high thermal stability

Active Publication Date: 2017-10-24
SUMITOMO CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] From the viewpoint of thermal stability, the above compounds are not sufficient as dyes for color filters used in display devices such as liquid crystal display devices.

Method used

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  • Compounds for Dyes
  • Compounds for Dyes
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Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0200] The compound (I) of the present invention can be produced, for example, based on the method described in Dyes and Pigments 2008, 77, 556. Specifically, it can be prepared by subjecting a compound represented by formula (pa1), a compound represented by formula (pa2) and ethyl cyanoacetate to a cyclization reaction in the presence of benzoic acid and a solvent. The reaction temperature is preferably 0°C to 200°C, more preferably 100°C to 150°C. The reaction time is preferably 1 hour to 24 hours, more preferably 8 hours to 18 hours, and still more preferably 8 to 16 hours. Examples of the solvent include methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, and N-methylpyrrolidone, among which 1-pentanol is preferred.

[0201]

[0202] [In formula (pa1) and formula (pa2), R 1 ~R 5 , R 7 ~R 9 , A, X and L represent the same meanings as above, respectively. ]

[0203] In the preparation of compound (I), relative to 1 mole of the compound represented by t...

Embodiment

[0436] Next, examples are given to further describe the present invention in detail. Unless otherwise specified, "%" and "part" in an example are mass % and a mass part.

[0437] In the following synthesis examples, the structures of the compounds were confirmed by NMR (JMM-ECA-500; manufactured by JEOL Ltd.) or mass spectrometry (LC; Model 1200, MASS manufactured by Agilent; LC / MSD model manufactured by Agilent).

[0438] The measurement of the weight average molecular weight (Mw) and the number average molecular weight (Mn) of polystyrene conversion of resin was performed on the following conditions by the GPC method.

[0439] Device: HLC-8120GPC (manufactured by Tosoh Co., Ltd.)

[0440] Column; TSK-GELG2000HXL

[0441] Column temperature; 40°C

[0442] Solvent; THF

[0443] Flow rate; 1.0mL / min

[0444] The concentration of solids in the tested liquid; 0.001~0.01% by mass

[0445] Injection volume; 50μL

[0446] Detector; RI

[0447] Calibration standards; TSK poly...

Synthetic example 1

[0452] Mix 10.6 parts of bis(3-amino-4-hydroxyphenyl)sulfone (manufactured by Tokyo Chemical Industry Co., Ltd.), 14.6 parts of 4-(diethylamino) salicylaldehyde (manufactured by Tokyo Chemical Industry Co., Ltd.), benzoic acid (Tokyo Chemical Industry Co., Ltd.) 3.17 parts, 1-pentanol (Tokyo Chemical Industry Co., Ltd.) 183 parts, and ethyl cyanoacetate (Tokyo Chemical Industry Co., Ltd. Hour. 14.6 parts of 4-(diethylamino) salicylaldehyde (manufactured by Tokyo Chemical Industry Co., Ltd.), 3.17 parts of benzoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) and ethyl cyanoacetate (manufactured by Tokyo Chemical Industry Co., Ltd.) were added to this reaction solution. Co., Ltd.) 8.61 parts, and stirred at 120 degreeC for 12 hours. After cooling the above reaction solution to room temperature, the precipitated crystals were obtained as a residue of suction filtration. After adding 236 parts of acetonitrile and 234 parts of isopropanol to this residue and stirring,...

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Abstract

The present invention provides a compound represented by formula (I) which is suitable for a dye of a color filter of a display device. [In the formula (I), L represents a divalent hydrocarbon group having 1 to 20 carbon atoms, or the like. A represents an aryl group or the like having 6 to 20 carbon atoms. X represents an oxygen atom, a sulfur atom, or the like. R1 to R4 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms, etc., or R1 and R3 are bonded to form a ring together with a carbon atom on an adjacent benzene ring and an adjacent nitrogen atom, or R2 and R4 is bonded to form a ring together with the adjacent carbon atoms on the benzene ring. R5 to R9 each independently represent a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, etc., or R5 and R6 are bonded to form a ring with adjacent carbon atoms, or R7 and R8 are bonded to adjacent carbon atoms together to form a ring.

Description

technical field [0001] The present invention relates to a compound and the like useful as a dye. Background technique [0002] Dyes are used, for example, to express colors by reflected light or transmitted light in the fields of fiber materials, liquid crystal display devices, inkjet printers, and the like. As such a dye, coumarin 6 (a compound represented by the following formula) is known (JP2006-154740-A Example 8). [0003] [0004] From the viewpoint of thermal stability, the compounds described above are not sufficiently satisfactory as dyes used in color filters of display devices such as liquid crystal display devices. Contents of the invention [0005] The present invention includes the following inventions. [0006] [1] A compound represented by formula (I). [0007] [0008] [In formula (I), [0009] L represents a divalent hydrocarbon group having 1 to 20 carbon atoms. The methylene group constituting the divalent hydrocarbon group can be replaced b...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D413/14C07D417/14C07D413/04C07D405/14C07D405/04C09B57/02G02B5/20G02F1/1335G03F7/004G03F7/027
CPCC07D405/14C07D413/14C07D417/14C09B57/00
Inventor 织田胜成藤田拓麻芦田徹
Owner SUMITOMO CHEM CO LTD