Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Color coupler for forming dye, silver halide photosensitive material and azomethine dyes compounds

A dye compound and color coupler technology, which is applied in the direction of azomethylamine dyes, organic dyes, azo dyes, etc., can solve problems such as insufficient image stability and vividness, reduced vividness, and blurred image outlines

Inactive Publication Date: 2006-03-15
FUJIFILM CORP
View PDF273 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since this dye blurred the outline of the image and lowered the vividness, it was not satisfactory.
In addition, the stability and vividness of the image are insufficient because of the side absorption at the bottom of the absorption peak of the absorption curve on the long-wave side, which affects the vividness of the image.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Color coupler for forming dye, silver halide photosensitive material and azomethine dyes compounds
  • Color coupler for forming dye, silver halide photosensitive material and azomethine dyes compounds
  • Color coupler for forming dye, silver halide photosensitive material and azomethine dyes compounds

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0205] Synthesis Example 1: Synthesis of Coupler-(1)

[0206] Coupler-(1) was synthesized according to the following route.

[0207]

[0208] Coupler (1)

[0209] To 38.8 g of 40% aqueous methylamine solution and 200 ml of acetonitrile solution, a total of 44.3 g of o-nitrobenzenesulfonyl chloride was added a little at a time while stirring in an ice bath. The temperature of the reaction system was raised to room temperature, and stirred for another 1 hour. Ethyl acetate and water were added for liquid separation, and the organic layer was washed with dilute hydrochloric acid and saturated brine. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off in vacuo to obtain 28.6 g of compound (A-1) crystallized from a mixed solvent of ethyl acetate and n-hexane.

[0210] Disperse 44.8g of reduced iron and 4.5g of ammonium chloride into 270ml of isopropanol and 45ml of water...

Synthetic example 2

[0215] Synthesis Example 2: Synthesis of Coupler-(3)

[0216] Coupler-(3) was synthesized according to the following route.

[0217]

[0218] Coupler(3)

[0219] To a solution of 438 g of 3-(2,4-di-tert-pentylphenoxy)propylamine, 210 ml of triethylamine, and 1 liter of acetonitrile, add a total of 333 g of o-nitrobenzenesulfonate in small amounts while stirring under an ice bath acid chloride. The temperature of the reaction system was raised to room temperature, and stirred for another 1 hour. Ethyl acetate and water were added for liquid separation, and the organic layer was washed with dilute hydrochloric acid and saturated brine. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off in vacuo to obtain 588 g of compound (B-1) crystallized from a mixed solvent of ethyl acetate and n-hexane.

[0220] Disperse 84.0 g of reduced iron and 8.4 g of ammonium chloride into ...

Synthetic example 3

[0225] Synthesis Example 3: Synthesis of Coupler-(6)

[0226] Coupler-(6) was synthesized according to the following route.

[0227]

[0228] Coupler(6)

[0229] To a solution of 21.4 g of dibenzamide and 200 ml of acetonitrile, a total of 39.9 g of o-nitrobenzenesulfonyl chloride was added in small amounts while stirring in an ice bath. The temperature of the reaction system was raised to room temperature, further 30 ml of triethylamine was added dropwise, and stirred for 1 hour. Ethyl acetate and water were added for liquid separation, and the organic layer was washed with dilute hydrochloric acid and saturated brine. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off in vacuo to obtain 31.2 g of compound (C-1) crystallized from a mixed solvent of ethyl acetate and n-hexane.

[0230] Disperse 44.8g of reduced iron and 4.5g of ammonium chloride into 270ml of isopropanol ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
Average particle sizeaaaaaaaaaa
Densityaaaaaaaaaa
Thicknessaaaaaaaaaa
Login to View More

Abstract

The dye-forming coupler is represented by formula (I), the silver halide photographic light-sensitive material contains the coupler and the azomethine dye is represented by formula (D). In the formulae, Q is a group -C(-R11)=C(-R12)-SO2-; R11 and R12 bond with each other to form, together with the -C=C- moiety, a 5- to 7-membered ring, or they each represent a hydrogen atom or a substituent; R1, R3 and R4 each represent a substituent; and m is an integer of 0-4. In formula (I), X represents a hydrogen atom or a group that splits off upon a coupling reaction with an oxidized product of a developing agent. In formula D, R5 and R6 each represent a hydrogen atom or a substituent; R7 represents a substituent; and n is an integer of 0-4. To provide a dye-forming coupler giving a dye having an excellent hue, a high molecular extinction coefficient and good storage stability, to provide a silver halide photographic light-sensitive material excellent in color reproducibility and sharpness and having good fastness of a color image.

Description

technical field [0001] The present invention relates to a dye-forming coupler that forms an imine dye by a coupling reaction with an oxidation product of a developer, and a silver halide photographic photosensitive material containing the coupler. The present invention also relates to the formimine dye compounds which can be prepared by the coupling reaction described above. Background technique [0002] According to the subtractive color method, in silver halide photographic photosensitive materials (hereinafter referred to as photosensitive materials sometimes), color images are formed by the three primary colors of yellow, magenta and cyan. In the color photographic process using the current p-phenylenediamine-based color developer, an acyl acetate aniline compound is used as a yellow coupler. However, due to the obvious side absorption at the bottom of the absorption peak in the absorption curve on the long-wave side, the color of the yellow dye obtained from these coup...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): G03C7/36G03C1/005C07D239/90C07D285/18C07D285/24C07D403/06C07D417/06C07D417/12C07D513/04C09B55/00G03C7/305
CPCG03C7/30535C09B55/002C07D417/06C07D285/18C07D403/06C07D513/04C09B55/003G03C7/36C07D239/90C07D417/12C07D285/24G03C1/08
Inventor 竹内洁上平茂生青木摩利男小笠原淳岛田泰宏市岛靖司出口泰章松田直人池田显御子柴尚菅井昌治胜又泰司
Owner FUJIFILM CORP
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com