US2835579A - N-alkyl and acylphenol coupler solvents for color photography - Google Patents

N-alkyl and acylphenol coupler solvents for color photography Download PDF

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Publication number
US2835579A
US2835579A US531813A US53181355A US2835579A US 2835579 A US2835579 A US 2835579A US 531813 A US531813 A US 531813A US 53181355 A US53181355 A US 53181355A US 2835579 A US2835579 A US 2835579A
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coupler
emulsion
solvent
solvents
alkyl
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US531813A
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John R Thirtle
Weissberger Arnold
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to US531813A priority Critical patent/US2835579A/en
Priority to FR1156115D priority patent/FR1156115A/en
Priority to GB26619/56A priority patent/GB820329A/en
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/388—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor
    • G03C7/3885—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor characterised by the use of a specific solvent

Definitions

  • the crystalloidal coupler solvents of the Jelley and Vittum patent have certain undesirable features when used in some photographic systems. For example, certain of the coupler solvents become yellow on aging or cause fading of the dyes formed in the emulsion. Some coupler solvents are unstable toward oxidation or tend to diffuse from the emulsion in which they are incor porated. All of these undesirable properties tend to degrade the final color picture.
  • coupler solvents which have' improved properties when used to dissolve the couplers and disperse them in photographic emulsion layers.
  • n to 17, n+n being 7 to 17
  • R should be an acyl group CO(CH ),,CH
  • couplersolvents possess good permeability to color developers and other processing solutions and do not have deleterious effects on the color of the dye images and stability of the emulsion layers. Also, our coupler solvents do not have a deleterious effect upon residual coupler left in the emulsion layer after processing.
  • a sensitive photographic silver halide emulsion such as silver halide in a water-soluble or permeable binder such as gelatin, polyvinyl alcohol or water-soluble synthetic resin is provided,
  • the mixture of coupler and coupler solvent is dispersed in discrete particles in the emulsion. and proportions of the coupler and coupler solvent are so chosen that the dispersed particles are liquid under the conditions of coating and processing the emulsion.
  • the invention therefore, includes a sensitive silver halide emulsion having a water-soluble or water-permeable binde'r such as gelatin in whichare dispersed particles of liquid consistency composed of coupler and coupler solvent.
  • the dispersion being stabilized if necessary with emulsifying agents such as those of the well-known higher fatty alcohol sulfate type.
  • the dispersion may be formed by dissolving the coupler and coupler solvent in a solvent of low boiling point such as butyl acetate, dispersing the solution in the gelatin solution or in water, and at a later stage removing the low-boiling solvent by evaporation.
  • Coupler 2-(2',4-di-tert. amylphenoxy acetamido)-4,6-dichloro-5-methylphenol (Graham U. S. application Serial No. 285,544) was dissolved in 3.0 cc. of 2,4-di-n-amylphenol by heating at C. The warm solution was poured into a mixture of 18 cc. of 10% gelatin solution, 2 cc. of water and 2 cc. of a 10% solution of Alkanol B (sodium tri-is opropyl naphthalene sulfonate).
  • Alkanol B sodium tri-is opropyl naphthalene sulfonate
  • the mixture was then emulsified by passing through a colloid mill and was then mixed with a gelatino-silver halide emulsion and coated. After drying in the usual manner, the emulsion was exposed and developed with Z-amino-S-diethylaminotoluene as the developing agent. After removal of the silver image a cyan dye image of satisfactory properties was obtained.
  • couplers illustrate the variety of compounds containing phenolic hydroxyl or active methylene
  • the nature groups which may be used with the coupler solvents of our invention I
  • couplers which may be dispersed by dissolving them in the coupler solvents of our invention are disclosed in Weissberger U. S. Patent 2,350,138; Porter et al. U. S. Patent 2,369,489, and Glass et al. U. S. Patents 2,453,661 and 2,455,169.
  • a gelatino-silver halide emulsion was made as described in Jelley and Vittum U. S. Patent 2,322,027, using 6- ⁇ a- 4 -[a-(2,4-di-tert-amylphenoxy)butyramidolphenoxy ⁇ - acetamido ⁇ -2,4-dichloro-3-methylphenol as the coupler and 2,4-di-tert. amylphenol as the coupler solvent.
  • a similar emulsion was made using 2,4-di-n-amylphenol, and the two emulsions were coated, incubated under heat conditions for severaldays, exposed and processed.
  • the coupler solvents of our invention are prepared by the reaction of cresols or of n-alkylphenols (Sandulesco and Girard, Bull. Soc. .Chim., vol. 47, 1930, page 1300) with aliphatic carboxylic acids in the presence of boron trifluoride.
  • the resulting ketones (acyl-n-alkyl phenols) may be used as suchor reduced by hydrogen and a catalyst to di-n-alkylphenols.
  • a light-sensitive photographic emulsion'for producing a colored image by color development comprising finely-divided liquid particles of a mixture of a coupler compound capable of coupling with the oxidation product of a primary aromatic amino developing agent and a coupler solvent having the structure where R and R are selected from the groups consisting of (CH ),,CH and --CO(CH ),,CH n is from 0 to '17, n+1: being from 7 to 17, and not more than one of R and R being a -CO(CH ),,CH group, said particles being dispersed in a light-sensitive silver halide-organic colloid emulsion.
  • a light-sensitive photographic emulsion for producing a colored image by color development comprising finelydivided liquid particles of a mixture of a coupler compound capable of coupling with the oxidation product of a primary aromatic amino developing agent and a coupler solvent having the structure where R and R are normal alkyl groups of not more than 18 carbon atoms, the total number of carbon atoms in R and R being from 9 to 19, said particles being dispersed in a light-sensitive silver halide-organic colloid emulsion.
  • a light-sensitive photographic emulsion for producing acolored image by color development comprising finely-divided liquid particles of a mixture of a coupler compound capable of coupling with the oxidation product of a primary aromatic amino developing agent and 2,4-
  • di-n-amylphenol as a coupler solvent, said particles being dispersed in a light-sensitive gelatino-silver halide emulsion.
  • a light-sensitive photographic emulsion for producing a colored image by color development comprising finely-divided liquid particles of a mixture of a coupler compound capable of coupling with the oxidation product of a primary aromatic amino developing agent and 2-noctyl-4-n-amylphenol as a coupler solvent, said particles being dispersed in a light-sensitive gelatino-silver halide emulsion.
  • a light-sensitive photographic emulsion for producing a colored image by color development comprising finely-divided liquid particles of a mixture of a coupler compound capable of coupling with the oxidation product of a primary aromatic amino developing agent and 2-nnonyl-4-n-amylphenol as a coupler solvent, said particles being dispersed in a light-sensitive gelatino-silver halide emulsion.
  • a light-sensitive photographic emulsion for producing a colored image by color development comprising finely-divided liquid particles of a mixture of a coupler compound capable of coupling with the oxidation product of a primary aromatic amino developing agent and 2- methyl-4-n-decylphenol as a coupler solvent, said particles being dispersed in a light-sensitive gelatino-silver halide emulsion.
  • a light-sensitive photographic emulsion for producing a colored image by color development comprising finely-divided liquid particles of a mixture of a coupler compound capable of coupling with the oxidation product of a primary aromatic amino developing agent and 2- methyl-4-n-octadecylphenol as a coupler solvent, said particles being dispersed in a light-sensitive gelatino-silver halide emulsion.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)

Description

Unitfid States Pa fit N-ALKYL AND ACYLPHENOL COUPLER SOL- VENTS FOR COLOR PHOTOGRAPHY John R. Thirtle and Arnold Weissberger, Rochester,
N. Y., assignors to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey No Drawing. Application August 31, 1955 Serial No. 531,813
7 Claims. (Cl. 96-97) This invention relates to color photography and particularly to novel coupler solvents for color-forming compounds used in coupling development.
Photographic processes in which color-forming compounds or couplers containing phenolic hydroxyl or active methyl groups which are capable of coupling with the oxidation product of a primary aromatic amino developing agent on photographic development to form dyes are now well known. A process of this type in which conplers are incorporated in silver halide emulsion layers by dispersing the couplers in a water-insoluble crystalloidal material such as tricresyl phosphate, which has a high solvent action for the coupler compound and the dye formed from it, was described in Jelley and Vittum U. S. Patent 2,322,027, granted June 15, 1943.
The crystalloidal coupler solvents of the Jelley and Vittum patent have certain undesirable features when used in some photographic systems. For example, certain of the coupler solvents become yellow on aging or cause fading of the dyes formed in the emulsion. Some coupler solvents are unstable toward oxidation or tend to diffuse from the emulsion in which they are incor porated. All of these undesirable properties tend to degrade the final color picture.
We have found a class of coupler solvents which have' improved properties when used to dissolve the couplers and disperse them in photographic emulsion layers.
It is therefore an object of .our invention to provide novel coupler solvents having improved properties. Another object is to provide coupler solvents which do not become discolored or cause fading of the dyes formed in the emulsion layer. A further object is to provide coupler solvents which are less diffusing than those hitherto used and which are more stable toward oxidation. Other objects will appear from the following description of our invention.
These objects are accomplished by dispersing the couplers in photographic emulsions in normal alkylphenol or acylphenol coupler solvents having the following structure:
n= to 17, n+n being 7 to 17 In these compounds there may be two alkyl groups but not more than one of R and R should be an acyl group CO(CH ),,CH
v 2,835,579 Patented May 20, was
' The following compounds may be used according to our invention:
2,4-di-n-amylphenol 2-n-octyl-4-n-amylphenol 2-n-nonyl-4-n-amylphenol 2-methyl-4-n-decylphenol 2-n-decyl-4-methylphenol 2-methyl-4-n-octadecylphenol 2-n-valeryl-4-n-amylphenol Our novel coupler solvents are used in the emulsion in amounts of from 0.05 to 3.0 parts per part of coupler. The quantity selected for use is determined by the solvent power and the effect which the particular coupler solvent produces on the dye absorption characteristics. Our
' couplersolvents possess good permeability to color developers and other processing solutions and do not have deleterious effects on the color of the dye images and stability of the emulsion layers. Also, our coupler solvents do not have a deleterious effect upon residual coupler left in the emulsion layer after processing.
According to the present invention, a sensitive photographic silver halide emulsion such as silver halide in a water-soluble or permeable binder such as gelatin, polyvinyl alcohol or water-soluble synthetic resin is provided,
and the mixture of coupler and coupler solvent is dispersed in discrete particles in the emulsion. and proportions of the coupler and coupler solvent are so chosen that the dispersed particles are liquid under the conditions of coating and processing the emulsion.
The invention, therefore, includes a sensitive silver halide emulsion having a water-soluble or water-permeable binde'r such as gelatin in whichare dispersed particles of liquid consistency composed of coupler and coupler solvent.
the like, the dispersion being stabilized if necessary with emulsifying agents such as those of the well-known higher fatty alcohol sulfate type. The dispersion may be formed by dissolving the coupler and coupler solvent in a solvent of low boiling point such as butyl acetate, dispersing the solution in the gelatin solution or in water, and at a later stage removing the low-boiling solvent by evaporation.
It is sometimes advantageous to employ a mixture of two or more of the novel coupler solvents in the same dispersion in order to obtain the desired combination of properties. Thus, one might use a mixture of one compound having exceptionally good solvent action with another compound added in correct proportions to give the final dispersion the desired refractive index, or to impart the desired absorption characteristics to the dye image.
The following example illustrates the method of incorporating a coupler in the emulsion according to our invention:
One gram of the coupler 2-(2',4-di-tert. amylphenoxy acetamido)-4,6-dichloro-5-methylphenol (Graham U. S. application Serial No. 285,544) was dissolved in 3.0 cc. of 2,4-di-n-amylphenol by heating at C. The warm solution was poured into a mixture of 18 cc. of 10% gelatin solution, 2 cc. of water and 2 cc. of a 10% solution of Alkanol B (sodium tri-is opropyl naphthalene sulfonate). The mixture was then emulsified by passing through a colloid mill and was then mixed with a gelatino-silver halide emulsion and coated. After drying in the usual manner, the emulsion was exposed and developed with Z-amino-S-diethylaminotoluene as the developing agent. After removal of the silver image a cyan dye image of satisfactory properties was obtained.
The following couplers illustrate the variety of compounds containing phenolic hydroxyl or active methylene The nature groups which may be used with the coupler solvents of our invention: I
Other couplers which may be dispersed by dissolving them in the coupler solvents of our invention are disclosed in Weissberger U. S. Patent 2,350,138; Porter et al. U. S. Patent 2,369,489, and Glass et al. U. S. Patents 2,453,661 and 2,455,169.
The following example illustrates the advantages of our coupler solvents in comparison with those of the prior art:
A gelatino-silver halide emulsion was made as described in Jelley and Vittum U. S. Patent 2,322,027, using 6-{a- 4 -[a-(2,4-di-tert-amylphenoxy)butyramidolphenoxy}- acetamido}-2,4-dichloro-3-methylphenol as the coupler and 2,4-di-tert. amylphenol as the coupler solvent. A similar emulsion was made using 2,4-di-n-amylphenol, and the two emulsions were coated, incubated under heat conditions for severaldays, exposed and processed. Tests for speed loss and contrast compared with coatings kept in a The coupler solvents of our invention are prepared by the reaction of cresols or of n-alkylphenols (Sandulesco and Girard, Bull. Soc. .Chim., vol. 47, 1930, page 1300) with aliphatic carboxylic acids in the presence of boron trifluoride. The resulting ketones (acyl-n-alkyl phenols) may be used as suchor reduced by hydrogen and a catalyst to di-n-alkylphenols.
It will be understood that theexamples and modifications described herein are illustrative only and that our invention is to be taken as limited only by the scope of the appended claims.
What we claim is:
1. A light-sensitive photographic emulsion'for producing a colored image by color development, comprising finely-divided liquid particles of a mixture of a coupler compound capable of coupling with the oxidation product of a primary aromatic amino developing agent and a coupler solvent having the structure where R and R are selected from the groups consisting of (CH ),,CH and --CO(CH ),,CH n is from 0 to '17, n+1: being from 7 to 17, and not more than one of R and R being a -CO(CH ),,CH group, said particles being dispersed in a light-sensitive silver halide-organic colloid emulsion.
2. A light-sensitive photographic emulsion for producing a colored image by color development, comprising finelydivided liquid particles of a mixture of a coupler compound capable of coupling with the oxidation product of a primary aromatic amino developing agent and a coupler solvent having the structure where R and R are normal alkyl groups of not more than 18 carbon atoms, the total number of carbon atoms in R and R being from 9 to 19, said particles being dispersed in a light-sensitive silver halide-organic colloid emulsion.
'3. A light-sensitive photographic emulsion for producing acolored image by color development, comprising finely-divided liquid particles of a mixture of a coupler compound capable of coupling with the oxidation product of a primary aromatic amino developing agent and 2,4-
, di-n-amylphenol as a coupler solvent, said particles being dispersed in a light-sensitive gelatino-silver halide emulsion.
4. A light-sensitive photographic emulsion for producing a colored image by color development, comprising finely-divided liquid particles of a mixture of a coupler compound capable of coupling with the oxidation product of a primary aromatic amino developing agent and 2-noctyl-4-n-amylphenol as a coupler solvent, said particles being dispersed in a light-sensitive gelatino-silver halide emulsion.
5. A light-sensitive photographic emulsion for producing a colored image by color development, comprising finely-divided liquid particles of a mixture of a coupler compound capable of coupling with the oxidation product of a primary aromatic amino developing agent and 2-nnonyl-4-n-amylphenol as a coupler solvent, said particles being dispersed in a light-sensitive gelatino-silver halide emulsion.
6. A light-sensitive photographic emulsion for producing a colored image by color development, comprising finely-divided liquid particles of a mixture of a coupler compound capable of coupling with the oxidation product of a primary aromatic amino developing agent and 2- methyl-4-n-decylphenol as a coupler solvent, said particles being dispersed in a light-sensitive gelatino-silver halide emulsion.
7. A light-sensitive photographic emulsion for producing a colored image by color development, comprising finely-divided liquid particles of a mixture of a coupler compound capable of coupling with the oxidation product of a primary aromatic amino developing agent and 2- methyl-4-n-octadecylphenol as a coupler solvent, said particles being dispersed in a light-sensitive gelatino-silver halide emulsion.
References Cited in the file of this patent UNITED STATES PATENTS 2,544,640 Chechak Mar. 13,1951
US531813A 1955-08-31 1955-08-31 N-alkyl and acylphenol coupler solvents for color photography Expired - Lifetime US2835579A (en)

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FR1156115D FR1156115A (en) 1955-08-31 1956-08-24 New emulsion for color photography and photographic products containing it
GB26619/56A GB820329A (en) 1955-08-31 1956-08-31 Improvements in colour photographic materials

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Cited By (23)

* Cited by examiner, † Cited by third party
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US2945761A (en) * 1957-07-29 1960-07-19 Eastman Kodak Co Reactivity of couplers incorporated in photographic emulsions
US3658546A (en) * 1969-03-20 1972-04-25 Agfa Gevaert Nv Method of incorporating photographic ingredients into photographic colloid compositions
EP0143570A2 (en) 1983-11-02 1985-06-05 Konica Corporation Silver halide color photographic material
US4551422A (en) * 1983-01-29 1985-11-05 Konishiroku Photo Industry Co., Ltd. Silver halide photographic light-sensitive material
US4952487A (en) * 1986-08-21 1990-08-28 Agfa-Gevaert Aktiengesellschaft Color photographic recording material
US4965179A (en) * 1985-04-19 1990-10-23 Fuji Photo Film Co., Ltd. Silver halide color photographic material
US5006437A (en) * 1988-09-02 1991-04-09 Konica Corporation Method of image formation using a silver ahlide color photographic material
US5270156A (en) * 1991-10-11 1993-12-14 Konica Corporation Silver halide color photographic light sensitive material
EP0579331A1 (en) * 1992-07-17 1994-01-19 Johnson & Johnson Clinical Diagnostics, Inc. Dry analytical element and method for the colorimetric determination of lithium ion
US5352561A (en) * 1991-12-06 1994-10-04 Eastman Kodak Company Thermal solvents for heat image separation processes
US5405736A (en) * 1992-01-21 1995-04-11 Eastman Kodak Company Dye stability with solid coupler solvent
US5429913A (en) * 1990-11-13 1995-07-04 Eastman Kodak Company Photographic coupler compositions containing ballasted alcohols and methods
US5451496A (en) * 1992-05-22 1995-09-19 Eastman Kodak Company Color photographic materials and methods containing DIR or DIAR couplers and phenolic coupler solvents
US5468587A (en) * 1993-06-08 1995-11-21 Eastman Kodak Company Hydrogen bond accepting groups on thermal solvents for image separation systems
US5480761A (en) * 1993-06-08 1996-01-02 Eastman Kodak Company Aliphatic hydroxyl hydrogen bond donating groups on thermal solvents for image separation systems
US5480760A (en) * 1993-06-08 1996-01-02 Eastman Kodak Company Sulfamoyl hydrogen bond donating groups on thermal solvents for image separation systems
US5726002A (en) * 1996-06-10 1998-03-10 Eastman Kodak Company Photographic element containing a particular cyan coupler dispersed in a phenolic solvent
US6525115B2 (en) 2000-12-05 2003-02-25 Eastman Kodak Company Method of making an aqueous dispersion of particles comprising an epoxy material for use in coatings
US20050040292A1 (en) * 2003-08-19 2005-02-24 Rollin Green Buckle for kites and the like
WO2012014954A1 (en) 2010-07-30 2012-02-02 富士フイルム株式会社 Novel azo compound, aqueous solution, ink composition, ink for inkjet recording, inkjet recording method, ink cartridge for inkjet recording and inkjet recording
WO2012014955A1 (en) 2010-07-30 2012-02-02 富士フイルム株式会社 Novel azo compound, aqueous solution, ink composition, ink for inkjet recording, inkjet recording method, ink cartridge for inkjet recording and inkjet recording
EP2455431A1 (en) 2003-10-23 2012-05-23 Fujifilm Corporation Ink and ink set for inkjet recording
EP2712894A1 (en) 2012-09-26 2014-04-02 Fujifilm Corporation Azo compound, aqueous solution, ink composition, ink for inkjet recording, inkjet recording method, ink cartridge for inkjet recording, and inkjet recorded material

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EP0711804A3 (en) 1994-11-14 1999-09-22 Ciba SC Holding AG Latent light stabilizers
GB2301444B (en) * 1995-03-23 1999-02-24 Eastman Kodak Co Photographic elements comprising cyan coupler dispersions with improved stability and increased activity
US5585230A (en) * 1995-03-23 1996-12-17 Eastman Kodak Company Cyan coupler dispersion with improved stability
US5726003A (en) * 1996-08-15 1998-03-10 Eastman Kodak Company Cyan coupler dispersion with increased activity

Citations (1)

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Publication number Priority date Publication date Assignee Title
US2544640A (en) * 1949-06-10 1951-03-13 Eastman Kodak Co Mixed grain photographic emulsions

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2544640A (en) * 1949-06-10 1951-03-13 Eastman Kodak Co Mixed grain photographic emulsions

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2945761A (en) * 1957-07-29 1960-07-19 Eastman Kodak Co Reactivity of couplers incorporated in photographic emulsions
US3658546A (en) * 1969-03-20 1972-04-25 Agfa Gevaert Nv Method of incorporating photographic ingredients into photographic colloid compositions
US4551422A (en) * 1983-01-29 1985-11-05 Konishiroku Photo Industry Co., Ltd. Silver halide photographic light-sensitive material
EP0143570A2 (en) 1983-11-02 1985-06-05 Konica Corporation Silver halide color photographic material
US4965179A (en) * 1985-04-19 1990-10-23 Fuji Photo Film Co., Ltd. Silver halide color photographic material
US4952487A (en) * 1986-08-21 1990-08-28 Agfa-Gevaert Aktiengesellschaft Color photographic recording material
US5006437A (en) * 1988-09-02 1991-04-09 Konica Corporation Method of image formation using a silver ahlide color photographic material
US5429913A (en) * 1990-11-13 1995-07-04 Eastman Kodak Company Photographic coupler compositions containing ballasted alcohols and methods
US5270156A (en) * 1991-10-11 1993-12-14 Konica Corporation Silver halide color photographic light sensitive material
US5436109A (en) * 1991-12-06 1995-07-25 Eastman Kodak Company Hydroxy benzamide thermal solvents
US5843618A (en) * 1991-12-06 1998-12-01 Eastman Kodak Company Hydrogen bond donating/accepting thermal solvents for image separation systems
US5352561A (en) * 1991-12-06 1994-10-04 Eastman Kodak Company Thermal solvents for heat image separation processes
US6277537B1 (en) 1991-12-06 2001-08-21 Eastman Kodak Company Dye diffusion image separation systems with thermal solvents
US5405736A (en) * 1992-01-21 1995-04-11 Eastman Kodak Company Dye stability with solid coupler solvent
US5451496A (en) * 1992-05-22 1995-09-19 Eastman Kodak Company Color photographic materials and methods containing DIR or DIAR couplers and phenolic coupler solvents
EP0579331A1 (en) * 1992-07-17 1994-01-19 Johnson & Johnson Clinical Diagnostics, Inc. Dry analytical element and method for the colorimetric determination of lithium ion
US5468587A (en) * 1993-06-08 1995-11-21 Eastman Kodak Company Hydrogen bond accepting groups on thermal solvents for image separation systems
US5480760A (en) * 1993-06-08 1996-01-02 Eastman Kodak Company Sulfamoyl hydrogen bond donating groups on thermal solvents for image separation systems
US5480761A (en) * 1993-06-08 1996-01-02 Eastman Kodak Company Aliphatic hydroxyl hydrogen bond donating groups on thermal solvents for image separation systems
US5726002A (en) * 1996-06-10 1998-03-10 Eastman Kodak Company Photographic element containing a particular cyan coupler dispersed in a phenolic solvent
US6525115B2 (en) 2000-12-05 2003-02-25 Eastman Kodak Company Method of making an aqueous dispersion of particles comprising an epoxy material for use in coatings
US20050040292A1 (en) * 2003-08-19 2005-02-24 Rollin Green Buckle for kites and the like
EP2455431A1 (en) 2003-10-23 2012-05-23 Fujifilm Corporation Ink and ink set for inkjet recording
WO2012014954A1 (en) 2010-07-30 2012-02-02 富士フイルム株式会社 Novel azo compound, aqueous solution, ink composition, ink for inkjet recording, inkjet recording method, ink cartridge for inkjet recording and inkjet recording
WO2012014955A1 (en) 2010-07-30 2012-02-02 富士フイルム株式会社 Novel azo compound, aqueous solution, ink composition, ink for inkjet recording, inkjet recording method, ink cartridge for inkjet recording and inkjet recording
EP2712894A1 (en) 2012-09-26 2014-04-02 Fujifilm Corporation Azo compound, aqueous solution, ink composition, ink for inkjet recording, inkjet recording method, ink cartridge for inkjet recording, and inkjet recorded material

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FR1156115A (en) 1958-05-13
GB820329A (en) 1959-09-16

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