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Dye compound having polymerizable group, and polymer containing same as monomer unit

A technology of polymerizable groups and compounds, applied in organic dyes, chemical instruments and methods, methine/polymethine dyes, etc., can solve the problems of weak solvent resistance, low solubility, and unimproved light resistance of pigments

Active Publication Date: 2020-04-24
KONICA MINOLTA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] On the other hand, in order to improve these, a large number of pyrazolone-based dyes and pyrazoloazole-based dyes have been proposed, for example, improvements in light and heat fastness have been proposed (Patent Documents 1 to 6), Insufficient performance, so further improvement is desired
[0005] In addition, in Patent Document 7, a proposal for improving solvent solubility is proposed, and in the above-mentioned application, it is applied in the form of a solution or a dispersion liquid, but since it is soluble in a desired organic solvent, in many cases, the It also becomes soluble in other organic solvents, and as a result, the solvent resistance after coating becomes weak
[0006] On the other hand, even other dyes have a problem of solvent resistance. As a countermeasure, for example, in Patent Document 8, triphenylmethane-based dyes are polymerized to improve heat resistance and solvent resistance. However, The original light resistance of the pigment is not improved enough
In addition, polymer dyes have problems in using them in various applications due to their low solubility.
[0007] In addition, Patent Document 9 proposes to improve solvent resistance by having a polymerizable group, but it is not sufficient, and further improvement is desired, and research is required.

Method used

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  • Dye compound having polymerizable group, and polymer containing same as monomer unit
  • Dye compound having polymerizable group, and polymer containing same as monomer unit
  • Dye compound having polymerizable group, and polymer containing same as monomer unit

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0184] (Example 1) Synthesis of an intermediate (compound 3A) illustrating compound 112

[0185] [Chemical 51]

[0186]

[0187] 6.74 g of compound 1A and 1.52 g of triethylamine were added to 100 ml of dichloromethane at room temperature, and after cooling to an internal temperature below -10°C, 3.08 g of compound 2A in dichloromethane was added dropwise below 0°C. After completion of dripping, it was made to react at 0 degreeC or less for 4 hours. Put 15ml of 1N-HCl at below 15°C, transfer to a separatory funnel, remove the water layer, wash the organic layer with water, neutralize, concentrate under reduced pressure, and purify the obtained residue by column chromatography, then decompose with hexane Analysis (dialysis), filtration, and drying gave an orange-red solid. Structure through MASS, 1 H-NMR and IR spectroscopy to identify.

Embodiment 2

[0188] (Example 2) Synthesis of an intermediate (compound 4A) illustrating compound 112

[0189] [Chemical 52]

[0190]

[0191] 7.57 g of compound 3A, 100 ml of 1N-HCl, and 3.32 g of potassium iodide were added to 100 ml of acetonitrile, heated to an internal temperature of 100° C., and reacted for 1 hour. The reaction solution was cooled to below 0°C, neutralized and washed with water, the organic layer was concentrated under reduced pressure, and the resulting residue was purified by column chromatography to obtain an orange-red solid. Structure through MASS, 1 H-NMR and IR spectroscopy to identify.

Embodiment 3

[0192] (Example 3) Synthesis of Exemplary Compound 112

[0193] [Chemical 53]

[0194]

[0195] 6.72 g of compound 4A and 3.24 g of triethylamine were added to 100 ml of dichloromethane, and after cooling to an internal temperature of 0° C. or lower, a dichloromethane solution of 2.72 g of acryloyl chloride was dropped at 0° C. or lower. After completion of the dropping, the reaction was made at an internal temperature of 0° C. or lower for 4 hours. Put 35ml of 1N-HCl at below 15°C, transfer to a separatory funnel, remove the water layer, wash the organic layer with water, neutralize, concentrate under reduced pressure, and purify the obtained residue by column chromatography, then decompose with hexane analysis, filtration, and drying to obtain an orange-red solid. Structure through MASS, 1 H-NMR and IR spectroscopy to identify.

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Abstract

Provided is a novel dye compound having a polymerizable group, the dye compound having excellent color characteristics, heat resistance, light fastness, and solvent resistance. Also provided is a polymer containing, as monomer units, the novel dye compound having a polymerizable group. This dye compound has a polymerizable group having a structure represented by general formula (1). (In the formula, R1, R2, and R3 each independently represent a polymerizable group or the like selected from among -R4-NR'-CO-L1-(OCO-R5C=CR6R7)n, -L1-NR'CO-R5C=CR6R7, and -NR'CO-R5C=CR6R7. X1 represents an oxygenatom or N-Y, and a ring may be formed by R1 and X1. Y represents a substituent. X2 represents -O-, -S-, -Se-, -NR8-, or -CR9R10-).

Description

technical field [0001] The present invention relates to a pigment compound having a polymerizable group and a polymer containing it as a monomer unit. Background technique [0002] Many pyrazolone-based dyes and pyrazoloazole-based dyes have been synthesized so far, and their usefulness has been confirmed and widely used. In recent years, it has been widely used in various applications such as photographic photosensitive materials, thermal transfer recording materials, color toners, optical recording media, and inkjet. [0003] In addition, as the performance required for the above-mentioned applications, for example, there are preferable spectral characteristics in color reproduction, solubility in desired organic solvents, high molecular absorption coefficient, fastness to light and heat, and resistance to various chemicals. Strong, easy to synthesize, stable, etc. [0004] On the other hand, in order to improve these, a large number of pyrazolone-based dyes and pyrazolo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/10C08F20/36C09B57/00C09B69/10
CPCC08F20/36C09B23/10C09B57/00C09B69/10C09B69/105C09B67/00
Inventor 大福幸司佐藤康之小野悦史
Owner KONICA MINOLTA INC