JPH0332059B2 - - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION This invention relates to light-sensitive silver halide photographic elements, particularly such elements with reduced graininess. Photographic silver halide elements containing incorporated color couplers have been known for many years. Coupler and the image dyes produced therefrom contain ballasting groups. The molecular size and shape of the stabilizing group will affect the coupler and image dye when coated, during and after processing.
It is like making it non-dispersive in the element. Such photographic materials are produced by a process involving color coupling development, which produces both a silver image and a dye image, and subsequent bleaching of the silver, leaving only the dye image. Since these materials are made to increase photographic speed, large silver halide grains are used. This results in increased graininess of the dye image, other things being equal. The problem that the present invention seeks to solve is to provide a silver halide photographic element comprising at least one silver halide emulsion layer and a non-dispersing dye-forming coupler associated with said silver halide emulsion, and having reduced graininess. It is to provide. In other words, the problem that the present invention seeks to solve is that despite improvements in photographic speed (refers to photographic sensitivity expressed in speed values; this term or the term "speed" is often used herein), grain It is an object of the present invention to provide a silver halide photographic element that does not have significant graininess (ie, exhibits reduced graininess). This problem is solved by the non-dispersible dye-forming coupler.
a first non-dispersible dye-forming coupler that produces a non-dispersible dye when reacted with the oxidized color developer; and a mobility that suppresses image blurring when reacted with the oxidized color developer. and a second non-dispersing dye-forming coupler yielding a dye of the above type. Thus, in accordance with the present invention, there is provided a silver halide photographic element having at least one silver halide emulsion layer and a non-dispersing dye-forming coupler associated with the silver halide emulsion layer, comprising: a first non-dispersible dye-forming coupler which forms a first non-dispersible dye by reaction with an oxidized color developer; a second non-dispersing dye coupler different from said first coupler to produce a second dye, said second dye having limited mobility and said first dye coupler; produces a controlled image spread within the photographic element when combined with a dye of : [Formula] (In the formula, COUP is the dye-generating coupler part, and the asterisk (*) indicates the coupling position,
The first stabilizing group (MAIN BALLAST) is a group that binds to the coupling position of COUP and can be separated from COUP by reaction of COUP with oxidized color developer, making the coupler non-diffusible. the size and shape, and the second stable group (SECONDARY BALLAST) is COUP
is a group attached to a non-coupler position of COUP
and a coupler that produces a diffusible dye and is represented by the following structural formula: [Formula] (In the formula, COUP is the dye-generating coupler part, and the asterisk (*) indicates the coupling position,
The stabilizing group is attached to the coupling position of COUP,
Due to the reaction between COUP and oxidized color developer
a group that is separable from COUP and has a size and shape that makes the coupler non-diffusible;
and SOL is a solubilizing substituent that binds to the non-coupling position of COUP and renders the dye produced by coupling COUP with the oxidized color developer diffusible in the alkaline environment present during photographic processing. a mordant for immobilizing said diffusible dye in combination with said second coupler-containing layer; . Here, "controlled image smearing" means that the formation of a dye cloud (also called a dye cloud), which is a state in which fine dye particles are dispersed around a single developer particle, is controlled. It means there is. That is, in the present invention, since the second dye has limited mobility, the dispersion of the dye particles is controlled, and therefore the formation of the dye cloud is controlled, and thus the close relationship with the dye cloud is controlled. The graininess of the particles is reduced. The relationship between graininess and pigment clouds is explained in, for example, the Photographic Society of Japan, Basics of Photographic Engineering - Silver Salt Photography Edition, pages 421-422 (January 1972), published by Corona Publishing Co., Ltd. can be found. Furthermore, in the specification of this application, "image spreading" is often explained using the term "image blurring," which is derived from the fact that the worse the graininess of the image, the worse the sharpness of the image. . In addition, the "spreading of the image" is defined by James, The
Theory of the Photographic Process (Fourth
Edition), P.351, 608-690, 620-621, 1977,
“image” used in Macmillan
It is used with the same concept as "spread".In fact,
According to the present invention, the image from the second dye derived from the second coupler exhibits only slight smearing at the edges of the image, and as a result of this controlled image spread, graininess is reduced. A decrease is obtained. When the elements of the invention contain only one halogen emulsion layer, that layer has a respective first and second coupler associated therewith. The element of the present invention is 1
When containing more silver halide emulsion layers, the first coupler is associated with at least one of those layers and the second coupler is associated with at least another of these emulsion layers. In the materials of the present invention, closely spaced image dye clouds spread into each other, and it is this effect that reduces graininess. In multicolor photographic materials, graininess reduction can be effected in any of the dye image-forming units. When the dye image-forming unit consists of more than one layer sensitive to the first region of the visible spectrum, the reduction in graininess may occur in each of the layers or in one of the layers.
It can be carried out in one layer, preferably in a more sensitive emulsion layer. Similarly, the reduction in graininess is
It can be done in a layer sensitive to each of the first regions of the visible spectrum or in just one or two such layers. Since a reduction in graininess in a given layer can reduce the sharpness of the image produced in that layer, layers whose graininess is reduced in accordance with the present invention are layers that produce dyes to which the naked eye is less sensitive, such as yellow. Preferably it is a dye-forming layer. Alternatively, the amount of silver normally used in the layer, where the image becomes blurred, can be reduced, but acceptable graininess is still achieved, thus allowing the emulsion layer to be thinner and therefore reducing sharpness in the underlying layers. increases. As will be clear to the photographic chemist, the nature of the components and intended processing methods of the photographic materials of the invention are
The choice is such that the increased mobility of the image dye leading to the desired reduction in graininess is balanced against the loss of sharpness that would occur if the image dye was allowed to spread over too large a distance. do. Image sharpness suppression according to the invention can be achieved in many ways. In a first embodiment, the blurring suppressing coupler is one that produces a slightly mobile dye such that the desired degree of image blurring occurs until processing and drying is complete. In a second embodiment, the coupler for suppressing image blurring includes:
A diffusible dye is produced, and the mordant of the dye is associated with the layer containing the coupler. In embodiments in which the element contains more than one silver halide emulsion layer, the coupler that suppresses image blurring may be the only dye-forming coupler in said layer or other dye-forming couplers, such as couplers that produce non-dispersible dyes. and may be present in the layer in an amount up to 99% by weight of the total dye-forming coupler therein. As the ratio of couplers that suppress image blurring increases with respect to other dye-forming couplers in the layer,
The degree of blurring of the resulting image increases. The coupler used in each embodiment has a stabilizing group at the coupling position that renders the coupler immobile. When coupled with an oxidized color developer, the stabilizing groups are separated so that the dye produced is not immobile and can thus diffuse through the layer and blur the image. The coupler used in the first embodiment has a second stabilizing group in the non-coupling position that makes the dye slightly mobile as desired. The coupler used in the second embodiment has a solubilizing substituent in the non-coupling position that makes the dye diffusible so that it can diffuse up to the mordant and be immobilized by the mordant. The coupler used in the first embodiment has the structural formula: [Formula] where COUP is the part of the dye-forming coupler, the asterisk (*) indicates its coupling position,
The first stabilizing group (MAIN BALLAST) is a group that binds to the coupling position of COUP and can be separated from COUP by reaction of COUP with oxidized color developer, which makes the coupler non-diffusible. The second stable group (SECONDARY BALLAST) is COUP
a group attached to a non-coupling position of COUP, which has a size and shape such that the dye formed by the reaction of COUP with an oxidized color developer is slightly mobile, and can be represented by . The coupler portion represented by COUP shall be any coupler portion known or used in the art to produce a colored reaction product with an oxidized color developer. You can also do it. Common yellow dye-producing couplers are acylacetanilides, such as acetoacetanilides and benzoylacetanilides; common magenta dye-producing couplers are pyrazolones, pyrazolotriazoles, pyrazolobenzimidazoles and indazolones. , and common cyan dye-forming couplers are phenols and naphthols. These couplers can generate the coupler part: COUP. The first stabilizing group shown above is of a molecular size and shape that renders the coupler non-diffusive.
The particular nature of the first stabilizing group is not critical, so long as it imparts non-diffusivity to the coupler. Useful first
Stable groups include alkyl groups and aryl groups having 8 to 32 carbon atoms. These groups can be unsubstituted or substituted, with substituents increasing the non-diffusivity of the coupler, changing the reactivity of the coupler, or reducing the stability of the stabilizing group after separation from the coupler. is a group that increases the diffusivity of The first stabilizing group contains a bridging group that connects the first stabilizing group to the coupling position of the coupler moiety. Typical crosslinking groups are oxy (-O-),
Includes thio (-S-) and azo (-N=N-). Preferred first stabilizing groups are alkoxy, aryloxy, alkylthio and arylthio groups containing 8 to 32 carbon atoms. The second stabilizing group is a group of appropriate size and bulk so as to make the dye slightly mobile. The particular second stabilizing group will depend on the particular coupler moiety used, the other substituents on that moiety, the particular color developer that couples with the coupler to form the dye, and the nature of the color developer substituents. Will. The particular second stabilizing group used is not critical, so long as it imparts the desired degree of mobility to the dye. Useful secondary stabilizing groups contain alkyl groups of 4 to 20 carbon atoms and aryl groups of 6 to 20 carbon atoms. These groups can be unsubstituted,
Alternatively, it can be substituted, the substituent being a group that alters the spectral absorption properties or diffusivity of the dye. For example, the second stabilizing group may contain basic ionizable groups, such as hydroxy groups, carboxylic acid groups, sulfonic acid groups, aminosulfonyl groups, and ionizable salts thereof, such that when it does not contain them, it is immobile. dyes can be slightly mobile. The second stabilizing group can contain a bridging group that connects it to the coupler moiety. Representative bridging groups are oxy, thio, carbonyl, carboxyl, amino, carbamoyl, aminocarbonyl, ureido, sulfamoyl and aminosulfonyl. A preferred yellow coupler useful in the first embodiment has the formula: where R ¹ is an aryl group, such as phenyl or an alkyl group, especially a tertiary alkyl group, such as tert-butyl, R ² is the first stabilizing group mentioned above, and R ³ is the second stabilizing group mentioned above. , and R ⁴ is hydrogen or one or more halogens,
is an alkyl or alkoxy group, and can be represented by Preferred cyan couplers useful in the first embodiment have the formula: and wherein R ² is as defined above and one of R ⁵ and R ⁶ is a second stabilizing group as described above. and the other is hydrogen or one or more halogen, alkyl, alkoxy or alkylamide. In particularly preferred couplers of this type, R ² is of the formula where R ⁷ is a solubilizing group, such as -COOH, -OH
or _-SO2NH2 , m is 5 to 20, and ^R5 is ^-CONHR8 , where ^R8 is alkyl of 6 to ₁₄ carbon atoms. A preferred magenta coupler useful in this embodiment has the formula:
[Formula] and [Formula] In the formula, R ² is as defined above, one of R ⁹ and R ¹⁰ is the above-mentioned second stabilizing group,
the other is hydrogen, alkyl, alkoxy, aryl or amino group, and R ¹¹ is hydrogen or one or more halogens,
is an alkyl, alkoxy or amino group. Unless otherwise indicated above, alkyl, alkoxy, and alkylamido substituents contain 1 to 8 carbon atoms, aryl substituents contain 6 to 10 carbon atoms, and amino substituents contain primary, Includes secondary and tertiary amino groups. These substituents and the first and second stabilizing groups are
It may be further substituted with groups such as halogen, hydroxy, carboxy, amino, amido, carbamoyl, sulfamoyl, sulfonamido, alkyl, alkoxy and aryl. In all cases, the substituents are selected such that the dye formed upon coupling has the desired slight mobility. The coupler used in the second embodiment is
Structural formula: [Formula] In the formula, COUP is the part of the dye-generating coupler, and the asterisk (*) indicates the coupling position,
The stabilizing group is attached to the coupling position of COUP,
Due to the reaction between COUP and oxidized color developer
SOL is a group separable from COUP, sized and shaped to make the coupler non-diffusible, and SOL is a solubilizing substituent that binds to the non-coupling position of COUP and oxidizes to COUP. The dye produced by coupling with the developer is
Diffusive in the alkaline environment present during photographic processing, can be expressed as: The part of the coupler represented by COUP is the first
The same as defined above in connection with couplers useful in the embodiments. Similarly, the group represented by the stabilizing group is the same as the first stabilizing group described above. The solubilizing group represented by SOL is an ionizable group that imparts the desired diffusivity to the dye produced by coupling, such as ionizable hydroxy, carboxylic acid, sulfonic acid, and aminosulfonyl groups and their ionizable groups. salts or contain them. One or more of these groups may be attached directly to the coupler moiety, or the SOL substituent may be of appropriate size,
For example, alkyl and aryl groups of 1 to 10 carbon atoms for alkyl groups and 6 to 12 carbon atoms for aryl groups, to which one or more ionizable groups are attached. Can be included. Such solubilizing groups may contain bridging groups that link the solubilizing group to the coupler moiety, similar to bridging groups that link the second stabilizing group to the coupler moiety. Preferred yellow, cyan and magenta couplers for use in this second embodiment have the structural formula ~ shown above, with the proviso that R ³ , R ⁵ or R ⁶ , and R ⁹ or R ¹⁰ are The second stabilizing group is replaced by a solubilizing group as defined above which can be represented by the groups R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁹ and R ²⁰ . Preferred solubilizing groups include 1) a carboxylic acid group attached directly to a non-coupling position on the coupler;
sulfonic acid groups or their ionizable salts,
2) 1 bound to a non-coupling position of the coupler and containing one or more carboxylic acid groups, sulfonic acid groups or ionizable salts thereof;
an alkyl group of ~10 carbon atoms or an aryl group of 6 to 12 carbon atoms, and attached to the uncoupled position via an amide or carbonyl group
This is the group in (2). The alkyl and aryl groups forming part of the solubilizing group may be further substituted with groups such as halogen, amino, amido, carbamoyl, sulfamoyl, sulfonamido, alkyl, alkoxy and aryl. In all cases these further substituents are selected such that the dye produced upon coupling has the desired diffusivity. The couplers used in the first and second embodiments exhibit a continuum with respect to mobility or diffusivity, with the coupler producing a slightly mobile dye at one extreme and a fully diffusive dye at the other extreme. Produces dye. Thus, a given group of atoms may be a secondary stabilizing group for a given coupler, depending on the particular coupler moiety to which it is attached, the nature of other substituents on that coupler moiety, and the particular developer used. can be,
and solubilizing groups for other couplers. Couplers useful in the present invention generally include:
It is a known compound and can be made by known techniques for making dye-forming couplers. Second
Certain couplers useful in embodiments are described in U.S. Pat.
Described in No. 3227550. A representative cyan dye-forming coupler is shown in the Examples below. Thus, the coupler of the present invention can be manufactured by a method similar to that shown in the following reaction scheme. The non-dispersing coupler that produces the non-dispersing dye used in this invention can be any known dye-forming coupler that produces a non-dispersing dye of the appropriate color. Such couplers are present in at least one halogenated emulsion layer and, as indicated above, can be present in the same layer as the coupler that suppresses image blurring. The color couplers used in the materials of the invention can be incorporated in conventional amounts by known methods. A typical amount of total dye-forming coupler in each layer is about 0.02 to 2 g/m ² . Hydrophobic couplers can be incorporated into the coupler solvent droplets, as is well known. Further details regarding couplers, methods of their incorporation, and various additives that can be used with these couplers can be found in Research Disclosure, Item 17643,
Listed in December 1978. Research
Disclosure is for Industrial Opportunities
Limited, Homewell, Havant Hampshire,
Published by PO91EF, United Kingdom. The mordant used in the second embodiment can be any mordant that immobilizes the dye formed as a result of the coupling reaction. Preferred mordants are basic polymeric mordants, such as polymers of aminoguanidine derivatives of vinyl methyl ketone, as described in U.S. Pat. No. 2,882,156, and U.S. Pat. No. 3,625,394;
3709690 and 3898088. Other useful mordants are U.S. Pat. No. 3,859,096 and
Research Disclosure, December 1976, 80-82
stated on the page. The greater the distance between the mordant and the color coupler, the greater the blurring of the image. Therefore, to minimize blurring,
A mordant is incorporated into the coupler-containing layer. Separating the mordant layer and the coupler layer, for example by interposing an inert intermediate layer of gelatin between them, can increase the blurring of the image. The amount of mordant used is preferably 0.1 to 5 g/m ² , more preferably
It is 0.3 to 1.5 g/ ^m2 . Although the photographic elements of this invention can be single color elements (including black and white elements), they are preferably multicolor elements, with blue sensitive or sensitized emulsions having in association yellow dye-forming color couplers. The unit consists of a green sensitized emulsion unit having an associated magenta dye-forming color coupler and a red sensitized emulsion unit having an associated cyan dye-forming color coupler. Each unit can be composed of a single emulsion layer or multiple emulsion layers sensitive to a given region of the visible spectrum. The layers of the element, including the layers of emulsion units, are
They can be arranged in various orders as known in the art. Couplers that produce dyes with increased mobility can be associated with only one or more of the emulsion layers. For example, since the human eye is less sensitive to sharpness in yellow images, it would be advantageous to have this coupler in conjunction with the blue sensitive layer. When the multilayer material of the invention contains a number of blue, green and red emulsion layers, there can be in each case relatively fast and relatively slow emulsion layers. Such materials are well known and are described, for example, in GB 1500497. In such cases, it is preferable to have a coupler that produces a dye of increased mobility associated with one or more sensitive layers. In the following description of suitable materials for use in elements of the invention, Research Disclosure, December
1978, Item 17643 (Industrial Opportunities
Limited, Homewell, Havant, Hampshire,
See PO9 1EF, United Kingdom).
This publication is hereinafter referred to as "Research Disclosure". The silver halide emulsions used in the elements of this invention can be negative or positive working. Suitable emulsions and their preparation are
and chapters of the Research Disclosure and the publications mentioned therein. Suitable vehicles for the emulsion layers and other layers of the elements of this invention are described in the Research Disclosure section and the publications mentioned therein. In addition to the couplers of the invention, elements of the invention can include additional couplers as described in Sections D, E, F and G of the Research Disclosure and the publications mentioned therein. . These couplers and the couplers of this invention can be incorporated into elements and emulsions as described in Section C of the Research Disclosure and the publications described therein. Photographic elements of the invention or their individual layers may contain brighteners (see Research Disclosure chapter), antifoggants and stabilizers (see Research Disclosure chapter), stain inhibitors and image dye stabilizers (see Research Disclosure chapter). and Section J), light-absorbing and scattering materials (Research
(see Disclosure chapter), curing agent (Research
(see Chapter XI of the Research Disclosure), plasticizers and lubricants (see Chapter XII of the Research Disclosure), matting agents (see Chapter XI of the Research Disclosure), and development regulators (see Chapter XI of the Research Disclosure)
can contain. Photographic elements can be coated on a variety of supports, as described in the Research Disclosure section and the publications listed therein. Photographic elements are exposed to actinic radiation, typically in the visible region of the spectrum, to produce a latent image, as described in the Research Disclosure section, and then exposed to active radiation, typically in the visible region of the spectrum, as described in the Research Disclosure section. It can be processed to produce a visible dye image. Processing to produce a visible dye image involves contacting the element with a color developer to reduce developable silver halide and oxidize the color developer. The oxidized color developer, in turn, reacts with the coupler to form a dye. A preferred color developer is p-phenylenediamine. Particularly preferred color developers are: 4-amino-N,N-diethyl-aniline hydrochloride, 4-amino-3-methyl-N-ethyl-N-
β-(methanesulfonamido)ethylaniline sulfate hydrate, 4-amino-3-methyl-N-ethyl-N-β-
Hydroxyethylaniline sulfate, 4-amino-3-β-(methanesulfonamide)
Ethyl-N,N-diethyl-aniline hydrochloride, and 4-amino-N-ethyl-N-(2-methoxyethyl)-m-toluidinedi-p-toluenesulfonic acid. With negative-working silver halide, this processing step produces a negative image. To obtain a positive (i.e., reversal) image, this step can be preceded by developing the exposed silver halide by developing with a non-chromogenic developer, in which the dye is formed. The element can then be uniformly covered to allow the unexposed silver halide to be developed. Alternatively, a direct positive emulsion can be used to obtain a positive image. Development is followed by bleaching, fixing or bleach-fixing to remove silver and silver halide, washing and drying according to conventional methods. As used herein, the term "non-diffusible" has the meaning normally applied to the term in photography, and for all practical purposes, , meaning a substance that does not migrate or wander through an organic colloid layer, such as a gelatin layer, when processed in a medium preferably with a pH of 10 or higher. The term "dispersible" has the opposite meaning and refers to a substance that has the property of effectively diffusing through the colloidal layer of a photographic element in an alkaline medium. The term "mobility" refers to the ability to spread.
The term "associated" means that the two substances in question interact during processing, and they are contained in the same layer or in adjacent layers. The following examples further illustrate the invention.
The experimental results are shown in Figures 1-5 of the accompanying drawings. Production Example 1 Production of a coupler producing a slightly mobile cyan dye (see reaction diagram above) 1(a) Ethyl-2-bromohexadecanoate (A) 2-bromohexadecanoic acid (10g, 30mmol) was heated to reflux with ethanol (2.4g, 52mmol) and benzene (10ml). The apparatus was equipped with a Dean Stark trap to collect the aqueous ethanol azeotrope distillate. A trace amount of concentrated sulfuric acid was required to catalyze the esterification. After about 2 hours, no more aqueous ethanol was removed in the reaction. After cooling, ethyl acetate (50 ml) was added and the solution was extracted several times with a solution of 2% sodium bicarbonate (NaHCO ₃ ) containing a small amount of sodium chloride. After washing with brine, the organic layer was dried over magnesium sulfate and evaporated to give a very pale yellow oil. This solidified in the refrigerator and had a melting point of about 20°C. Distillation is not necessary for purification. Yield: 10g, 93% C ₁₈ H ₃₅ BrO ₂ Theoretical value: C59.50; H9.64; Br22.04% Actual value: C59.48; H9.53; Br21.97% 1(b) Kuplar (B) 1,4-dihydroxy-2-naphtonic acid (5.3
g, 26 mmol) in dry, degassed dimethyl sulfoxide (DMSO) (100 ml) and diluted with 50%
An oil dispersion of sodium hydride (2.6 g, 52 mmol) was added with stirring at room temperature under a nitrogen atmosphere. The mixture was stirred and heated at 70-80° C. in a nitrogen atmosphere until foaming ceased. After cooling to room temperature, the bromoester (A)
(9.5 g, 26 mmol) was added together with dry dimethylformamide (DMA) (40 ml). 1 hour later
The mixture was poured into dilute hydrochloric acid and the crude product was filtered, washed with water and dried. Recrystallization was carried out from ligroin. Yield: 9.2g, 73% C ₂₉ H ₄₂ O ₆ Theoretical value: C71.60; H8.64% Actual value: C71.15; H8.54% 1(c) Acid chloride (C) Naphthol (B) ( (8.7 g, 18 mmol) was converted to the acid chloride by stirring with thionyl chloride (50 ml) and (20 ml) at room temperature for 2 hours. The volatiles were dried in vacuo at 35-40°C to yield the acid chloride as a yellow/green solid.
Purification is unnecessary. Yield: Quantitative 1(d) Kuplar (D) The acid chloride (C) was dissolved in dry ethyl acetate (100 ml) and this solution was dissolved in octylamine (4.7 g, 3 mmol) in dry ethyl acetate (50 ml). Added portionwise to the stirred solution at room temperature. After stirring for 2 hours, the amine hydrochloride was removed by filtration.
The liquid was then evaporated to give an oil which soon crystallized. Recrystallization was carried out in acetic acid containing a few drops of water. Yield: 8.5g (79%) _C37H59NO5.1 / _2H2O Theoretical value _: C73.27; H9.90; _N2.31 Actual value: C73.02; H9.67; N2.21% 1 (e) Product Coupler Coupler (D) (6.0 g, 10 mmol) was dissolved in dimethylformamide (80 ml) at room temperature under nitrogen atmosphere. To this was added 10% aqueous sodium hydroxide (15ml). After the hydrolysis was complete (30 minutes), the reaction mixture was poured into dilute hydrochloric acid (1) with ice. The product was removed by filtration, washed with water and dried. Recrystallization was carried out from acetic acid. Yield: 3.0g (53%) C ₃₅ H ₅₅ NO ₅ Theoretical value: C73.81; H9.67; N2.46 Actual value: C73.54; H9.81; N2.15% Similar method for other couplers Manufactured by. Their structural formulas and elemental analysis values are listed in the table below. Table: Example 1 Structures described below containing dye-forming units sensitive to blue, green and red, each consisting of a relatively sensitive layer and a relatively less sensitive layer , g/m ² ) was produced (coating A). The dye coupler in this and subsequent examples was incorporated into the silver halide by the coupler's solvent. [Table] [Table] Base of cellulose acetate film

Claims (1)

Claims: 1. A silver halide photographic element having at least one silver halide emulsion layer and a non-dispersing dye-forming coupler associated with said silver halide emulsion layer, comprising: said non-dispersing dye-forming coupler; The coupler produces a first non-dispersible dye by reaction with the oxidized color developer; the first non-disperse dye-forming coupler produces a second non-disperse dye by reaction with the oxidized color developer; a second non-dispersible dye coupler different from said first coupler, said second dye having limited mobility and producing a dye of said first dye; a coupler which, when combined, produces a controlled image spread within the photographic element, and wherein the second coupler produces a dye having limited mobility and is represented by the following structural formula: (In the formula, COUP is the dye-generating coupler part, and the asterisk (*) indicates its coupling position,
The first stabilizing group is a group that is attached to the coupling position of the COUP and that can be separated from the COUP by reaction of the COUP with an oxidized color developer, and that has a size and size such that the coupler is non-diffusible. The second stabilizing group is a group attached to a non-coupling position of COUP and has a size and shape such that the dye formed by the reaction of COUP with the oxidized color developer is slightly mobile. and a coupler that produces a diffusible dye and is represented by the following structural formula: [Formula] (where COUP is the dye-producing coupler part, and the asterisk (*) indicates the coupling position. show,
The stabilizing group is attached to the coupling position of COUP,
Due to the reaction between COUP and oxidized color developer
a group that is separable from COUP and has a size and shape that makes the coupler non-diffusible;
and SOL is a solubilizing substituent that binds to the non-coupling position of COUP and renders the dye produced by coupling COUP with the oxidized color developer diffusible in the alkaline environment present during photographic processing. A silver halide photographic element selected from the group consisting of: a mordant which immobilizes said diffusible dye in combination with said second coupler-containing layer;