US3700455A - Color photograph containing fade-preventing agents - Google Patents

Color photograph containing fade-preventing agents Download PDF

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Publication number
US3700455A
US3700455A US3700455DA US3700455A US 3700455 A US3700455 A US 3700455A US 3700455D A US3700455D A US 3700455DA US 3700455 A US3700455 A US 3700455A
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United States
Prior art keywords
color
color image
r4
r3
r2
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Expired - Lifetime
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Hidehiko Ishikawa
Mikio Sato
Syun Takada
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Konica Minolta Inc
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Konica Minolta Inc
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    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/392Additives
    • G03C7/39208Organic compounds
    • G03C7/39212Carbocyclic
    • G03C7/39216Carbocyclic with OH groups

Abstract

A COMPOUND OF THE FORMULA,

2-((2-(HO-),3-R1,5-R3-PHENYL)-X-),4-R4,6-R2-PHENOL

WHEREIN R1, R2, R3 AND R4 ARE INDIVIDUALLY A STRAIGHT CHAIN OR BRANCHED-CHAIN HYDROCARBON RADICAL HAVING 1 TO 18 CARBON ATOMS, THE TOTAL SUM OF CARBON ATOMS OF SAID R1, R2, R3 AND R4 BEING LESS THAN 32; AND X IS -S-, -O-, -SO2 OR

-(CH(-R5))N-

WHERE N IS AN INTEGER OF 0 TO 3, AND R5 IS A HYDROGEN ATOM OR A LOWER ALKYL GROUP, AND A COLOR IMAGE-FORMING DYE ARE INCORPORATED INTO A SILVER HALIDE PHOTOGRAPHIC COMPOSITION. WHEN DEVELOPED, A COLOR IMAGE HAVING IMPROVED LIGHT FASTNESS IS OBTAINED. AN ULTRAVIOLET RAY ABSORBING AGENT AND/OR A COLOR COUPLER MAY BE INCORPORATED INTO THE COMPOSITION.

Description

"United States Patent Ofice US. Cl. 96-400 4 Claims ABSTRACT OF THE DISCLOSURE A compound of the formula,

OH OH wherein R R R and R are individually a straight chain or branched-chain hydrocarbon radical having 1 to 18 carbon atoms, the total sum of carbon atoms of said R R R and R being less than 32; and X is -S, -O, SOg or where n is an integer of to 3, and R is a hydrogen atom or a lower alkyl group, and a color image-forming dye are incorporated into a silver halide photographic composition. When developed, a color image having improved light fastness is obtained. An ultraviolet ray absorbing agent and/ or a color coupler may be incorporated into the composition.

The present invention relates to a color photograph bearing a color image comprising an azomethine, indoaniline or the like dye together with a phenol derivative as a fading-preventing agent.

It is well known that a color photograph is obtained by subjecting a light-sensitive silver halide color photographic material to color development according to the oxidation condensation reaction of primary aromatic amino compound with a coupler, thereby forming a color image comprising an azomethine, indoaniline, indophenol or the like dye. In this case, substractive color photography is employed for reproduction of the color image, and cyan, magenta and yell-ow dyes are formed by the color development, in general. Ordinarily, the cyan dye is formed from a phenol or naphthol type coupler, the magenta dye from a pyrazolone type coupler, and the yellow dye from an acylacetamide type coupler. These couplers are added to developers or have previously been incorporated into silver halide photographic emulsions.

However, it is also well known that a color image formed according to such color development process as mentioned above is not satisfactory in fastness resistance chiefly to ultraviolet rays or visible light (hereinafter referred to as light fastness), and is faded with relative ease when irradiated with ultraviolet rays or visible light. In order to overcome the above-mentioned drawbacks, there have heretofore been studied many processes for improving a color image in light fastness by incorporating an ultraviolet ray-absorbing agent into a light-sensitive silver halide color photographic material, thereby decreasing the dose of ultraviolet rays irradiated to the 3,700,455 Patented Oct. 24, 1972 resulting color image. However, in order to impart satisfactory light fa'stness to a color image by use of an ultraviolet ray-absorbing agent, a large amount of said agent agent is required, thereby the color image is greatly stained due to coloration of the ultraviolet ray-absorbing agent itself. Further, the use of an ultraviolet ray-absorbing agent is not efiective at all for prevention of the fading of color image due to visible light, and thus the improvement in light fastness of color image by use of an ultraviolet ray-absorbing agent has a limit.

In view of such actual state as mentioned above, we made studies for years in order to improve the lightfastness of color images formed by color development of light-sensitive silver halide color photographic materials. As the result, it has been found that the light fastness of a developed color image is greatly improved by making present, together with a dye in the developed color image, a bisphenol derivative of the general formula,

wherein R R R and R are individually a straight chain or branched chain hydrocarbon radical having 1 to 18 carbon atoms, the total sum of carbon atoms of said R R R and R being less than 32; and X is S, -O, SO or i L \t. l.

where n is an integer of 0 to 3; and R is hydrogen atom or a lower alkyl group.

The above-mentioned fading-preventing agent employed in the present invention is used for the improvement in light fastness of cyan, magenta and yellow color images formed by color development. Cyan, magenta and yellow couplers to be used for the formation of these color images are not limited, and may be any of such types that they are alkali-soluble and alkali solutions thereof are incorporated into silver halide photographic emulsions, and that they are dissolved in a high boiling organic solvent to give a solution which can be dispersed in an aqueous gelatine solution or added to silver halide photographic emulsions.

The fading-preventing agent employed in the present invention may be incorporated into any or all of the layers of a light-sensitive silver halide photographic materials, i.e. photographic emulsion layers in which cyan, magenta and yellow dyes will be formed by color development. Further, when applied to a transfer diffusion method, the fading-preventing agent may be incorporated not only into such photographic emulsion layers as mentioned above but also into receptive layers. That is, it is suflicient that the fading-preventing agent is made present together with any or all of dyes forming the color image of a finallyobtained photograph.

The fading-preventing agent used in the present invention is hardly water-soluble, and it is dissolved in a low boiling organic solvent such as methyl acetate, ethyl acetate, carbon tetrachloride, chloroform, methanol, ethan, n-butanol, dioxane, acetone, benzene, dimethylformamide or dimethyl sulfoxide, a high boiling solvent such tricresyl phosphate, di-n-butyl phthalate or ethyl N,N-diphenyl carbamate, or a mixed solvent comprising said low and high boiling solvents. The resulting solution is charged into a protective colloid solution, dispersed by means of a colloid mill or a homogenizer and then added to, for example, a silver halide photographic emulsion containing a coupler. Depending on the type of the coupler, the fading-preventing agent and the coupler may be dissolved in an organic solvent and then added to an aqueous gelatine solution or the like.

Examples of the fading-preventing agent used in the present invention are as shown below, but these are, of course, not limitative.

The amount of the fading-preventing agent to be added varies depending on the kind of said agent and the coupler employed and on the kind of the layer to which the agent is applied, but is usually within the range from 1 to 100% by weight based on the weight of the coupler. A silver halide photographic emulsion containing the fading-preventing agent and a coupler is coated on a support such as baryta paper or film base to form a photographic emulsion layer. Into this photographic emulsion layer, or a lower or upper layer thereof, may be incorporated an ultraviolet ray-absorbing agent. Thus the fading-preventing agent of the present invention can be used in combination with the ultraviolet ray-absorbing agent, whereby the light fastness of the resulting color image can be enhanced. Examples of the ultraviolet rayabsorbing agent to be used in the above case are benzophenone, acrylonitrile, thiazolidone, benzotriazole, stilbene, oxazole, thiazole and imidazole type compounds, though these are, of course, not limitative.

When, as mentioned above, dyes forming the color image of a color photograph are made present together with a fading-preventing agent represented by the aforesaid general formula, the resulting developed color image is markedly improved in fastness to ultraviolet rays and visible light, as will be clear from the examples set forth later. Further, all the fading-preventing agents used in the present invention are substantially colorless and hence do not stain the resulting color images.

The incorporation of the fading-preventing agent does not bring about any injury in the color development, and even when it is made present together with a dye formed by color development, no change in hue is observed. Moreover, the fading-preventing agent has no detrimental interactions with other photographic additives.

The present invention is illustrated below with reference to examples.

EXAMPLE 1 2 g. of the exemplified compound (4) was dissolved in a mixed solution of 1 g. of tricresyl phosphate and 4 g. of ethyl acetate. The resulting solution was added to 40 cc. of a 5% aqueous gelatine solution containing saponin and then dispersed by means of a homogenizer. The whole amount of the resulting dispersion was added to 400 cc. of a silver chlorobromide emulsion containing 10 g. of sodium l-hydroxy-N-octadecyl-2-naphthamide-4-sulfonate (coupler). Thereafter, the emulsion was coated on a baryta paper and then dried to prepare a sample of the present invention.

For comparison, a control sample was prepared in the same manner as above, except that the compound (4) was not used.

The sample of the present invention and the control sample were individually exposed to white light, subjected to color development, stopping, fixing, bleaching, waterwashing and drying, and exposed for 5, l0 and 20 hours by means of a Xenon fade meter to calculate the percentage (D/D0 of the density after exposure (D) to the density before exposure (D0). The results were as shown in Table 1.

As is clear from the results shown in Table 1, the light fastness of the sample of the present invention is greatly improved.

EXAMPLE 2 A mixture comprising 8.0 g. of the cyan coupler 2- (p-tert-amylphenoxy-p-benzoyl)-amino 4 chloro 5- methylphenol, 3.0 g. of the exemplified compound (2) and 3.0 g. of the ultraviolet ray-absorbing agent 2-(2-hydroxy- 3,5-di-tert-butylphenol)-benzotriazo1e was dissolved in a mixed solution of 8 g. of tricresyl phosphate and 20 g. of ethyl acetate. The resulting solution was added to 200 cc. of a 5% aqueous gelatine solution containing saponin and then dispersed by means of a homogenizer. Subsequently, the resulting dispersion was added to 400 cc. of a redsensitive silver iodobromide emulsion, which was then coated on a film base, followed by drying, to prepare a sample (I) of the present invention.

Further, a control sample, a sample (II), and a sample (III) were prepared in the same manner as above, except that there were not used, respectively, both the exemplified compound (2) and the ultraviolet ray-absorbing agent.

The samples (I) to (III) and the control sample were individually exposed to white light, subjected to color development, stopping, fixing, bleaching washing and drying, and then exposed for 10, 20 and 40 hours by means of a xenon fade meter to measure the density variation of the samples in the same manner as in Example 1. The results were as shown in Table 2.

TABLE 3 Sample D/DoX 100 Control sample 70 53 38 Sample: I 100 100 96 98 96 87 III 83 66 50 Exposure time (hrs) 6 From the results of Table 2, it is evident that the samples (I) and (III) of the present invention show excellent light fastness, which is further enhanced by use of the exemplified compound (2) in combination with the ultraviolet ray-absorbing agent.

EXAMPLE 3 A mixture comprising 10 g. of the magenta coupler 1-(2,4dimethyl 6 chlorophenyl-7,3-{3-[a-(3-pentadecylphenoxy)butylamide]benzamide}-5-pyrazolone and 4 g. of the exemplified compound (1) was dissolved in a mixed solution of 5 g. of dibutyl phthalate and 20 g. of ethyl acetate. The resulting solution was added to 200 cc. of a 5% aqueous gelatine solution containing saponin and then dispersed by means of a homogenizer. Subsequently, the dispersion was added to 350 cc. of a greensensitized silver chlorobromide emulsion, which was then coated on a baryta paper.

On the other hand, 7 g. of the same ultraviolet rayabsorbing agent as in Example 2 was dissolved in a solution of 10 g. of tricresyl phosphate in 20 g. of ethyl acetate. The resulting solution was added to 300 cc. of a 10% aqueous gelatine solution containing saponin and then dispersed by means of a homogenizer. The thus obtained dispersion was coated on the aforesaid silver chlorobromide emulsion layer so that the amount of the ultraviolet ray-absorbing agent became 7 mg. per 100 cmfi, followed by drying, to prepare a sample (I).

Further, samples (II) and (III) and a control sample were prepared in the same manner as above, except that there were not used, respectively, the ultraviolet rayabsorbing agent, the exemplified compound (1), and both the ultraviolet ray-absorbing agent and the exemplified compound (1).

The thus prepared samples (I) to (IE) and the control sample were individually subjected to the same photographic treatments as in Example 1, and then exposed for 5, 10 and 20 hours by means of a xenon fade meter to calculate the density variation of the samples in the same manner as in Example 1. The results were as shown in Table 3.

From the results of Table 3, it is clear that the samples (I) and (II) of the present invention are excellent in light fastness.

What we claim is:

1. A color composition which upon development produces a color image having improved light fastness, said composition comprising (a) a silver halide photographic emulsion (b) a compound of the formula,

OH OH 20 I wherein R R R and R are individually a straight chain or branched-chain hydrocarbon radical having 1 to 18 carbon atoms, the total sum of carbon atoms of said R R R and R being less than 32, and X is s -o-, or

35 where n is an integer of 0 to 3 and R is a hydrogen References Cited UNITED STATES PATENTS 2,688,625 9/1954 Bell et a1. 96-56 2,735,765 2/1956 Loria et a1. 96-56 3,271,156 9/ 1966 Sawdey 96-56 J. TRAVIS BROWN, Primary Examiner US. Cl. X.R.

US3700455D 1969-09-05 1970-08-31 Color photograph containing fade-preventing agents Expired - Lifetime US3700455A (en)

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GB (1) GB1267287A (en)

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3936305A (en) * 1973-12-03 1976-02-03 Mitsubishi Paper Mills, Ltd. Color photographic photosensitive material containing ultraviolet ray-absorbing compound
US4174220A (en) * 1976-10-30 1979-11-13 Konishiroku Photo Industry Co., Ltd. Color photographic materials containing dye fading inhibitors
US4178184A (en) * 1976-10-23 1979-12-11 Konishiroku Photo Industry Co., Ltd. Color photographic materials containing dye-fading inhibitors
US4266020A (en) * 1978-10-05 1981-05-05 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material
US4286042A (en) * 1978-06-06 1981-08-25 Fuji Photo Film Co., Ltd. Light reflecting layer for color diffusion transfer photographic system
US4446219A (en) * 1981-08-17 1984-05-01 Agfa-Gevaert Aktiengesellschaft Photographic material comprising a layer with Ni complex of 2,2'-bisphenol
EP0147854A2 (en) 1983-12-29 1985-07-10 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive materials
US4551422A (en) * 1983-01-29 1985-11-05 Konishiroku Photo Industry Co., Ltd. Silver halide photographic light-sensitive material
EP0204175A1 (en) 1985-05-09 1986-12-10 Fuji Photo Film Co., Ltd. Silver halide color photographic materials
EP0209118A2 (en) 1985-07-17 1987-01-21 Konica Corporation Silver halide photographic material
EP0239363A2 (en) 1986-03-25 1987-09-30 Konica Corporation Light-sensitive silver halide photographic material feasible for high speed processing
EP0242013A2 (en) 1986-01-20 1987-10-21 Konica Corporation Silver halide color photographic light-sensitive material
EP0256537A2 (en) 1986-08-15 1988-02-24 Fuji Photo Film Co., Ltd. Color print and a method for producing the same
US4824771A (en) * 1986-12-18 1989-04-25 Eastman Kodak Company Photographic acetanilide couplers with novel ballast group and photographic elements containing them
US4983506A (en) * 1987-10-14 1991-01-08 Fuji Photo Film Co., Ltd. Silver halide photographic material
US5049473A (en) * 1988-03-17 1991-09-17 Fuji Photo Film Co., Ltd. Method of preserving colored images
US5108886A (en) * 1989-12-18 1992-04-28 Fuji Photo Film Co., Ltd. Silver halide color photographic material
US5120636A (en) * 1989-05-25 1992-06-09 Fuji Photo Film Co., Ltd. Silver halide color photographic material containing magenta coupler, specific organic solvent and bisphenol compound
US5122444A (en) * 1988-08-15 1992-06-16 Fuji Photo Film Co., Ltd. Silver halide color photographic material containing a magenta couplers and color fading preventing agent
US5294529A (en) * 1989-10-30 1994-03-15 Fuji Photo Film Co., Ltd. Silver halide color photographic material containing magenta coupler, image-dye stabilizer and high boiling coupler solvent
US5437962A (en) * 1993-04-02 1995-08-01 Eastman Kodak Company Photographic elements containing particular color couplers in combination with particular stabilizers
US5441855A (en) * 1993-06-21 1995-08-15 Agfa-Gevaert Ag Color photographic recording material
US5466569A (en) * 1993-06-21 1995-11-14 Agfa-Gevaert Ag Color photographic recording material
EP0698817A1 (en) 1994-08-22 1996-02-28 AGFA-GEVAERT naamloze vennootschap Assortment of silver halide photographic industrial X-ray films and method of processing said assortment
US5543280A (en) * 1994-11-24 1996-08-06 Agfa-Gevaert Ag Colour photographic recording material
US5561028A (en) * 1994-06-24 1996-10-01 Mitsubishi Paper Mills Limited Silver halide photographic photosensitive material
EP0800113A2 (en) 1996-04-05 1997-10-08 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US6337170B1 (en) * 1997-06-06 2002-01-08 Fuji Photo Film Co., Ltd. Color diffusion transfer image forming material

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8610610D0 (en) * 1986-04-30 1986-06-04 Kodak Ltd Stabilization of dye images
DE68922547T2 (en) * 1988-08-24 1995-08-17 Fuji Photo Film Co Ltd A color photographic silver halide material.
US5441861A (en) * 1992-09-08 1995-08-15 Agfa-Gevaert Ab Color photographic silver halide material
US5891613A (en) * 1997-08-22 1999-04-06 Eastman Kodak Company Silver halide light-sensitive element
US6312881B1 (en) * 2000-01-14 2001-11-06 Eastman Kodak Company Photographic element with yellow dye-forming coupler and stabilizing compounds
US6555306B1 (en) 2001-12-21 2003-04-29 Eastman Kodak Company Photographic element with dye-forming coupler and image dye stabilizing compound
US6846620B1 (en) 2003-06-27 2005-01-25 Albert J. Mura, Jr. Photographic element with dye-forming coupler and image dye stabilizing coupler solvent

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3936305A (en) * 1973-12-03 1976-02-03 Mitsubishi Paper Mills, Ltd. Color photographic photosensitive material containing ultraviolet ray-absorbing compound
US4178184A (en) * 1976-10-23 1979-12-11 Konishiroku Photo Industry Co., Ltd. Color photographic materials containing dye-fading inhibitors
US4174220A (en) * 1976-10-30 1979-11-13 Konishiroku Photo Industry Co., Ltd. Color photographic materials containing dye fading inhibitors
US4286042A (en) * 1978-06-06 1981-08-25 Fuji Photo Film Co., Ltd. Light reflecting layer for color diffusion transfer photographic system
US4266020A (en) * 1978-10-05 1981-05-05 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material
US4446219A (en) * 1981-08-17 1984-05-01 Agfa-Gevaert Aktiengesellschaft Photographic material comprising a layer with Ni complex of 2,2'-bisphenol
US4551422A (en) * 1983-01-29 1985-11-05 Konishiroku Photo Industry Co., Ltd. Silver halide photographic light-sensitive material
EP0147854A2 (en) 1983-12-29 1985-07-10 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive materials
EP0204175A1 (en) 1985-05-09 1986-12-10 Fuji Photo Film Co., Ltd. Silver halide color photographic materials
EP0209118A2 (en) 1985-07-17 1987-01-21 Konica Corporation Silver halide photographic material
EP0242013A2 (en) 1986-01-20 1987-10-21 Konica Corporation Silver halide color photographic light-sensitive material
EP0239363A2 (en) 1986-03-25 1987-09-30 Konica Corporation Light-sensitive silver halide photographic material feasible for high speed processing
EP0256537A2 (en) 1986-08-15 1988-02-24 Fuji Photo Film Co., Ltd. Color print and a method for producing the same
US4824771A (en) * 1986-12-18 1989-04-25 Eastman Kodak Company Photographic acetanilide couplers with novel ballast group and photographic elements containing them
US4983506A (en) * 1987-10-14 1991-01-08 Fuji Photo Film Co., Ltd. Silver halide photographic material
US5049473A (en) * 1988-03-17 1991-09-17 Fuji Photo Film Co., Ltd. Method of preserving colored images
US5122444A (en) * 1988-08-15 1992-06-16 Fuji Photo Film Co., Ltd. Silver halide color photographic material containing a magenta couplers and color fading preventing agent
US5120636A (en) * 1989-05-25 1992-06-09 Fuji Photo Film Co., Ltd. Silver halide color photographic material containing magenta coupler, specific organic solvent and bisphenol compound
US5294529A (en) * 1989-10-30 1994-03-15 Fuji Photo Film Co., Ltd. Silver halide color photographic material containing magenta coupler, image-dye stabilizer and high boiling coupler solvent
US5108886A (en) * 1989-12-18 1992-04-28 Fuji Photo Film Co., Ltd. Silver halide color photographic material
US5437962A (en) * 1993-04-02 1995-08-01 Eastman Kodak Company Photographic elements containing particular color couplers in combination with particular stabilizers
US5466569A (en) * 1993-06-21 1995-11-14 Agfa-Gevaert Ag Color photographic recording material
US5441855A (en) * 1993-06-21 1995-08-15 Agfa-Gevaert Ag Color photographic recording material
US5561028A (en) * 1994-06-24 1996-10-01 Mitsubishi Paper Mills Limited Silver halide photographic photosensitive material
EP0698817A1 (en) 1994-08-22 1996-02-28 AGFA-GEVAERT naamloze vennootschap Assortment of silver halide photographic industrial X-ray films and method of processing said assortment
US5543280A (en) * 1994-11-24 1996-08-06 Agfa-Gevaert Ag Colour photographic recording material
EP0800113A2 (en) 1996-04-05 1997-10-08 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US6337170B1 (en) * 1997-06-06 2002-01-08 Fuji Photo Film Co., Ltd. Color diffusion transfer image forming material

Also Published As

Publication number Publication date
JPS4831256B1 (en) 1973-09-27
DE2043270C3 (en) 1978-03-02
DE2043270B2 (en) 1977-07-07
DE2043270A1 (en) 1971-03-18
GB1267287A (en) 1972-03-15

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