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1,1-dimethyl-3-propyl sulfonate indole-1'-(n,n-dimethyl amine athyl amine)-3-ethyl imidazole carbocxyanine dyestuff, preparing process and use thereof

A dimethylaminoethylamino, propanesulfonic acid-based indolyl technology, applied in the field of photosensitive chemistry, can solve the problem of fog rise, difficult formation of silver chloride chemical non-stoichiometric lattice defects, inability to meet T-grain emulsions, etc. problem, to achieve the effect of increasing the sensitivity

Inactive Publication Date: 2006-03-29
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the inherent defects of silver chloride T-grain emulsions, for example, its compatibility with iodine is not as easy as that of bromine and iodine, and the formation of stoichiometric lattice defects of silver chloride is difficult and the amount is relatively small; Cl - Stimulated without Br - It is so easy to be stimulated, and the concentration, lifetime, and migration of light free electrons are not as easy to adjust as silver bromide, which leads to a low basic sensitivity of the silver chloride emulsion, and it is difficult to sensitize, and it is foggy at the same time. will rise sharply
We realize that in order to realize the practical application of silver chloride emulsion, we must solve the problem of sensitization of silver chloride emulsion, and the existing sensitizing dyes can no longer meet the requirements of T-grain emulsions, and synthesize new and efficient spectral sensitizing dyes , it is imminent to solve the problem of sensitization of silver chloride emulsion

Method used

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  • 1,1-dimethyl-3-propyl sulfonate indole-1'-(n,n-dimethyl amine athyl amine)-3-ethyl imidazole carbocxyanine dyestuff, preparing process and use thereof
  • 1,1-dimethyl-3-propyl sulfonate indole-1'-(n,n-dimethyl amine athyl amine)-3-ethyl imidazole carbocxyanine dyestuff, preparing process and use thereof
  • 1,1-dimethyl-3-propyl sulfonate indole-1'-(n,n-dimethyl amine athyl amine)-3-ethyl imidazole carbocxyanine dyestuff, preparing process and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation of 1,1-dimethyl-3-propanesulfonylindolyl-1'-(N,N-dimethylaminoethylamino)-3'-ethyl-imidazolyl-carbocyanine dye:

[0037] One. formula (II) compound, i.e. the preparation of 1-(N, N-dimethylaminoethylamino)-2-methyl-3-ethyl imidazole iodonium salt

[0038] 1) Preparation of o-(N,N-dimethylaminoethylamino)-nitrobenzene

[0039] In a 500ml three-necked flask, add 57.2g (0.283mol) of 2-chloronitrobenzene, 33.2g (0.283mol) of N,N-dimethylethylenediamine and 70.0g of anhydrous sodium acetate, and the reactants are mixed After that, it turns red soon, and is heated to 140°C to 150°C under stirring, and kept for 10 hours. As the reaction proceeded, the reaction mixture gradually became viscous. After the reaction was completed, the reaction mixture was naturally cooled to room temperature, 500ml of water was added thereto for dilution, and then 30ml of hydrochloric acid (30wt%) was added, at this moment, unreacted raw material 2-chloronitrobenzene was precipitated...

Embodiment 2

[0069] Spectral sensitization of compounds of the present invention in cubic silver chlorobromide microcrystalline emulsion:

[0070] 1. Preparation of cubic silver chlorobromide microcrystalline emulsion:

[0071] In a container with a volume of 2 liters, add 500 ml of deionized water, 8 g of gelatin, 0.15 g of sodium chloride, and 1.2 g of potassium iodide in advance, and heat to a constant temperature of 65° C. Add 12.5 milliliters of 0.1 mol / liter concentration of silver nitrate aqueous solution and 12.5 milliliters of 0.1 mol / liter concentration of sodium chloride solution under high-speed stirring, then add 100 milliliters of 4 mol / liter concentration of silver nitrate solution and 100 milliliters of A mixed solution of sodium chloride and potassium bromide at a concentration of 4 mol / liter (wherein the molar ratio of sodium chloride to potassium bromide=5:1). After the reaction, cool down to 30°C, then add 20 milliliters of 10wt% sodium polystyrene sulfonate solution a...

Embodiment 3

[0079] Spectral sensitization of compounds of the present invention in cubic silver bromoiodide microcrystalline emulsion:

[0080] 1. Preparation of cubic silver bromide iodide microcrystalline emulsion:

[0081] In a container with a volume of 4 liters, add 1000 ml of deionized water, 20 g of gelatin, 1.0 g of sodium chloride, and 2.5 g of potassium iodide in advance, heat to 70° C., and keep the temperature constant. Under high-speed stirring, add 10.0 milliliters of 0.4 mol / liter concentration of silver nitrate aqueous solution and 10.0 milliliters of 0.4 mol / liter concentration of potassium iodide and potassium bromide solution in 1 minute (wherein the molar ratio of potassium iodide and potassium bromide=1:5) Then add the silver nitrate solution of 92 milliliters of 2.0 mol / liter concentration and the mixed solution of potassium iodide and potassium bromide of 92 milliliters of 2.0 mol / liter concentration (wherein the mol ratio=1:5 of potassium iodide and potassium bromi...

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Abstract

A 1,1-dimethyl-3-propanesulfonindo-1'-(N, N-dimethylamino ethanamino)-3'-ethyl- imiazolyl-carbocyanine dye used as the optical spectrum sensitivity dye for the photographic emulsion is prepared through the condensation reaction between 1-(N, N-dimethylamino ethanamino)-2-methyl-3-ethyl imidazole iodine salt and 1,1-dimethyl-2-phenylaminovinyl-3-propanesulfono indole in the nitrobenzene under existance of triethylamine and acetic anhydride as condensating agent.

Description

technical field [0001] The invention belongs to the field of photosensitive chemistry and relates to 1,1-dimethyl-3-propanesulfonyl indolyl-1'-(N,N-dimethylaminoethylamino)-3'-ethyl-imidazolyl - Carbocyanine dyes and their preparation and use as sensitizing dyes in photographic emulsions. Background technique [0002] Photographic organic compounds are important components of photographic emulsions. The improvement of photographic performance, the improvement of quality and the development of new varieties of emulsions are inseparable from the application of photographic organic compounds. Sensitizing dye is an important part of photographic organic matter, and it is one of the important means for improving the sensitivity of photographic silver halide emulsion. After more than one hundred years of development and research, the number of sensitizing dyes has reached tens of thousands. Although there is such a huge family of sensitizing dyes, it is still impossible to accu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/02G03C1/14
Inventor 陈丽娟慈颖李智徐海涛彭必先
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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