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Maskpin colour coupler

A color coupler and general formula technology, applied in multi-color photographic technology, photographic technology, optics, etc., can solve the problem of not fundamentally eliminating harmful absorption, etc., and achieve improved color reproduction quality, increased sensitivity, and high coupling activity Effect

Inactive Publication Date: 2005-10-05
沈阳感光化工研究院有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In order to reduce or eliminate the harmful absorption of pyrazolone nitrogen methine dyes in the blue zone, people have carried out continuous exploration and research on the structure of pyrazolone couplers, and have received certain results; Eliminate harmful absorption fundamentally, because the molecular structure of pyrazolone azmethene dye determines its spectral absorption performance

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Embodiment 1: (synthesis of exemplary compound M-01)

[0038] N-[4-chloro-3-[[4-[(3-carboxy-4.5-dimethoxyphenyl)azo]-4.5-dihydro-5-oxo-1-(2.4.6-tri Chlorophenyl)-1H-pyrazol-3-yl]amino]phenyl]-2-[3-(1.1-dimethylethyl)-4-hydroxyphenoxy]-tetradecamide (referred to as M- 01)

[0039] Intermediate 1:

[0040] 2. Synthesis of 3-dimethoxybenzoic acid

[0041] Reaction formula:

[0042]

[0043] Operation method:

[0044] In a 100 ml three-necked flask, add 25 grams of water and 2.5 grams of potassium bicarbonate, and after heating to 95°C, add 2 grams of 2.3-dimethoxybenzaldehyde. Then, 2.5 grams of potassium permanganate solution dissolved in 50 grams of water was added dropwise, and incubated for 2 hours. After cooling to room temperature, it was filtered, and the filtrate was acidified with concentrated hydrochloric acid to pH=1, and a solid precipitated. Filter, wash with water, and dry to obtain 1.7 g of white solid powder, melting point: 122-124°C.

[0045] In...

Embodiment 2

[0064] Embodiment 2: (synthesis of exemplary compound M-17)

[0065] N-[4-chloro-3-[[4-[(4-carboxymethoxyphenyl)azo]-4.5-dihydro-5-oxo-1-(2.4.6-trichlorophenyl) -1H-pyrazol-3-yl]amino]phenyl]-2-[3-(1.1-dimethylethyl)-4-hydroxyphenoxy]-tetradecamide (M-17 for short)

[0066] Intermediate 1:

[0067] Synthesis of p-nitrophenoxyacetic acid

[0068] Reaction formula:

[0069]

[0070] Operation method:

[0071] In a 250 ml three-necked flask, add 110 ml of water and 12.5 g of sodium hydroxide in sequence. After stirring and dissolving, 21 grams of p-nitrophenol was added, and a mixed solution of 15 grams of chloroacetic acid and 35 milliliters of water was added dropwise. Then, the temperature was raised to reflux, and after insulation for 3 hours, a mixed solution of 7.5 grams of chloroacetic acid, 6.5 grams of sodium hydroxide and 30 milliliters of water was added dropwise, and the reflux reaction was continued for 6 hours. Then, it was cooled to room temperature, acidi...

Embodiment 3

[0085] Embodiment 3: (synthesis of exemplary compound M-19)

[0086] N-[4-chloro-3-[[4-[(4-hydroxyethoxyphenyl)azo]-4.5-dihydro-5-oxo-1-(2.4.6-trichlorophenyl) -1H-pyrazol-3-yl]amino]phenyl]-2-[3-(1.1-dimethylethyl)-4-hydroxyphenoxy]-tetradecamide (M-19 for short)

[0087] Intermediate 1:

[0088] Synthesis of p-Nitrophenoxyethanol

[0089] Reaction formula:

[0090]

[0091] Operation method:

[0092] In a 100 ml three-necked flask, 75 ml of water, 2.6 g of sodium hydroxide, and 8.8 g of p-nitrophenol were successively added. The temperature was raised to 80° C., 5.6 g of chloroethanol was added dropwise, and then refluxed for 30 hours. After cooling to room temperature, filter, wash with water, and dry to obtain 5 grams of off-white powder with a melting point of 82-83°C.

[0093] Intermediate 2:

[0094] Synthesis of p-aminophenoxyethanol

[0095] Reaction formula:

[0096]

[0097] Operation method:

[0098] In a 100ML three-necked flask, add 4.0 grams of p...

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Abstract

The structural general expression of the compound is I:R1. The position 2 possesses H or CL. The position 5 possesses aromatic group replaced by nonproliferation group or alkyl group and hydroxyl group. Where, m=0.1; R2 is the substituent of the diazonium constituent. The characteristics are that the R2 substitutent of the diazonium constituent possesses aromatic group replaced by the group containing alkyl oxide, alkyl sulfide or alkoxyl with water-solubility group. The invented compound can correct the harmful absorption in the blue section caused by the coloring matter formed from the color former of pyrazolene class so as to raise the color reductive quality. The compound provides high coupling activity so as to raise the light sensitivity of the film greatly.

Description

technical field [0001] The invention relates to a color photosensitive material, in particular to a Musk product coupler. Background technique [0002] Pyrazolone color coupler is a color coupler (such as CP-263) commonly used in the green layer of color photosensitive materials. It couples with the oxidation product of the color developer to generate pyrazolone azmethene dyes; The absorption spectrum is in the most sensitive area of ​​human vision, so its spectral absorption characteristics have a major impact on color reproduction; this dye not only has the first absorption band in the green light area of ​​530-550nm, but also has a blue color at 430-440nm. There is a second absorption band in the region; the existence of the second absorption band causes color distortion and affects color reproduction, so the second absorption band is also called a harmful absorption band. In order to reduce or eliminate the harmful absorption of pyrazolone nitrogen methine dyes in the b...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G03C7/30G03C7/384
Inventor 王达力周兆秋李秀峰王凤举代秀全
Owner 沈阳感光化工研究院有限公司
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