WO1990010253A1 - The use of pyrazolo-triazole photographic colour couplers - Google Patents
The use of pyrazolo-triazole photographic colour couplers Download PDFInfo
- Publication number
- WO1990010253A1 WO1990010253A1 PCT/GB1990/000232 GB9000232W WO9010253A1 WO 1990010253 A1 WO1990010253 A1 WO 1990010253A1 GB 9000232 W GB9000232 W GB 9000232W WO 9010253 A1 WO9010253 A1 WO 9010253A1
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- WIPO (PCT)
- Prior art keywords
- group
- coupler
- alkyl
- pyrazolo
- silver halide
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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
- G03C7/32—Colour coupling substances
- G03C7/36—Couplers containing compounds with active methylene groups
- G03C7/38—Couplers containing compounds with active methylene groups in rings
- G03C7/381—Heterocyclic compounds
- G03C7/382—Heterocyclic compounds with two heterocyclic rings
- G03C7/3825—Heterocyclic compounds with two heterocyclic rings the nuclei containing only nitrogen as hetero atoms
- G03C7/3835—Heterocyclic compounds with two heterocyclic rings the nuclei containing only nitrogen as hetero atoms four nitrogen atoms
Definitions
- This invention relates to the use of lH-pyrazolo[l,5-b]-l,2,4—triazole couplers in photographic materials.
- lH-Pyrazolo[1,5,-b]-l,2, -triazole couplers have been described in, for example, US Patent 4,621,046.
- European Patent Specification 0,177,765 such a coupler having the formula:
- the coupler is said to provide dye images of good fastness and freedom from yellow stain.
- photographic colour paper processable in the RA4 process is comprised of silver halide emulsions having at least 80% silver chloride and preferably substantially pure silver chloride.
- Most lH—pyrazolo[l,5—b]—l,2,4—triazole couplers when incorporated into silver chloride emulsions provide photographic materials having poor raw stock keeping properties. That is, the material when stored after manufacture but before exposure and processing, shows ' significantly increased D . compared to freshly coated materials.
- the present invention is directed to the use of certain 1H—pyrazolo[l,5—b]—1,2,4—triazole couplers in photographic silver chloride materials to improve their raw stock keeping properties. Accordingly the present invention is directed to the use of lH-pyrazolo[l,5-b]-l,2,4- triazole couplers containing a tertiary carbon group on the coupler nucleus in photographic silver halide materials of which the halide comprises more than 80% chloride, in order to improve raw stock stability.
- the present invention also provides a photographic material comprising a support bearing at least one photosensitive silver halide emulsion of which the halide is at least 80% molar chloride having in or adjacent the emulsion layer a lH-pyrazolo[l,5-b]-l,2,4—triazole coupler containing a tertiary carbon group on the coupler nucleus.
- the silver halide emulsion comprises at least 90% silver chloride especially substantially pure silver chloride.
- the preferred couplers have the formula
- R 1 and R3 are each an alkyl or substituted alkyl group
- R is a hydrogen or a coupling off group, at least one of R 1 and R3 comprising a group of the formula:
- R4, R5 and R6 are individually a halogen atom or an alkyl, cycloakyl, amino, aryl, cyano, nitro, heterocyclic or — —R group wherein L is a linking group and R is an alkyl, aryl, heterocyclic group and
- R 1 or R3 are a tertiary alkyl group they preferably contain 4-8 carbon atoms and may be t-butyl, t-pentyl or t—octyl. R 1 and R3 may otherwise contain 1—25 carbon atoms and may comprise a ballast group to render the coupler non—diffusible in photographic layers.
- R 4, R5 and R6 are chlorine, bromine and fluorine; alkyl groups containing 1 to 20 carbon atoms, for example, methyl, ethyl, propyl, butyl, pentyl, ethylhexyl and eicosyl; cyclohexyl and cyclopentyl; dioctylamino, dimethylamino and dodecylamino; aryl containing 6 to 20 carbon atoms, or example, phenyl, naphthyl and mesityl; cyano; nitro; a heterocyclic group comprised of atoms selected from carbon, oxygen, nitrogen and sulphur atoms necessary to complete a 5— or 6-membered ring, for example, pyrrolyl, oxazolyl and pyridyl.
- L are:
- alkyl such as alkyl containing 1 to 30 carbon atoms, for example, methyl, ethyl, propyl, butyl or eicosyl, or aryl, such as aryl containing 6 to 20 carbon atoms, for example, phenyl or naphthyl; or a heterocyclic group comprised of atoms selected from carbon, nitrogen, oxygen, and sulphur atoms necessary to complete a 5- or 6— ember heterocyclic ring, for example, pyrrolyl, oxazolyl and pyridyl.
- R examples include an alkyl containing 1 to 30 carbon atoms, for example, methyl, ethyl, propyl, butyl, pentyl and eicosyl; aryl, such as aryl containing 6 to 20 carbon atoms, for example, phenyl and napthyl; or a heterocyclic group, such as a 5- or 6—membered heterocyclic group comprised of atoms selected from carbon, nitrogen, oxygen and sulphur atoms, for example an oxazole, pyridine, pyrrole or thiophene ring.
- R5 and R6 form a heterocyclic ring this may be an oxazole, pyridine, pyrrole and thiophene; or when they form an alicyclic ring system, this may be cyclohexyl, norbornyl or adamantyl.
- the coupling-off group R may be a halogen atom or an aryloxy or arylthio group.
- the couplers used in the present invention may be prepared by methods known in the art. Typically, the couplers are associated with a silver halide emulsion layer coated on a support to form a photographic element. As used herein, the term "associated with” signifies that the coupler is incorporated in the silver halide emulsion layer or in a layer adjacent thereto where, during processing, it is capable of reacting with silver halide development products.
- the photographic elements can be single colour elements or multicolour elements.
- the magenta dye-forming couplers of this invention would usually be associated with a green—sensitive emulsion, although they could be associated with an emulsion sensitised to a different region of the spectrum, or with a panchromatically sensitised, orthochromatically sensitised or unsensitised emulsion.
- Multicolour elements contain dye image— orming units sensitive to each of the three primary regions of the spectrum. Each unit can be comprised of a single emulsion layer or of multiple emulsion layers sensitive to a given region of the spectrum.
- the layers of the element, including the layers of the image-forming units can be arranged in various orders as known in the art.
- a typical multicolour photographic element comprises a support bearing yellow, magenta and cyan dye image-forming units comprising at least one blue-, green- or red-sensitive silver halide emulsion layer having associated therewith at least one yellow, magenta or cyan dye-forming coupler respectively, at least one of the magenta dye-forming couplers being a coupler of this invention.
- the element can contain additional layers, such as filter and barrier layers.
- the silver halide emulsion employed in the elements of this invention can be either negative-working or positive— orking. Suitable emulsions and their preparation are described in Research Disclosure Sections I and II and the publications cited therein. Suitable vehicles for the emulsion layers and other layers of elements of this invention are described in Research Disclosure Section IX and the publications cited therein.
- the elements of the invention can include additional couplers as described in Research Disclosure Section VII, paragraphs D, E, F and G and the publications cited therein.
- the couplers of this invention and any additional couplers can be incorporated in the elements and emulsions as described in Research Disclosures of Section VII, paragraph C and the publications cited therein.
- the photographic elements of this invention or individual layers thereof can contain brighteners (see Research Disclosure Section V), antifoggants and stabilisers (see Research Disclosure Section VI), antistain agents and image dye stabiliser (see Research Disclosure Section VII, paragraphs I and J), light absorbing and scattering materials (see Research Disclosure Section VIII), hardeners (see Research Disclosure Section XI), plasticisers and lubricants (see Research Disclosure Section XII), antistatic agents (see Research Disclosure Section XIII), matting agents (see Research Disclosure Section XVI) and development modifiers (see Research Disclosure Section XXI).
- brighteners see Research Disclosure Section V
- antifoggants and stabilisers see Research Disclosure Section VI
- antistain agents and image dye stabiliser see Research Disclosure Section VII, paragraphs I and J
- light absorbing and scattering materials see Research Disclosure Section VIII
- hardeners see Research Disclosure Section XI
- plasticisers and lubricants see Research Disclosure Section XII
- antistatic agents see Research Disclosure Section XIII
- matting agents see Research Disclosure
- the photographic elements can be coated on a variety of supports as described in Research Disclosure Section XVII and the references described therein.
- Photographic elements can be exposed to actinic radiation, typically in the visible region of the spectrum, to form a latent image as described in Research Disclosure Section XVIII and then processed to form a visible dye image as described in Research Disclosure Section XIX.
- Processing to form a visible dye image includes the step of contacting the element with a colour developing agent to reduce developable silver halide and oxidise the colour developing agent. Oxidised colour developing agent in turn reacts with the coupler to yield a dye.
- Preferred colour developing agents are p-phenylene diamines.
- this processing step leads to a negative image.
- this step can be preceded by development with a non-chromogenic developing agent to develop exposed silver halide, but not form dye, and then uniform fogging of the element to render unexposed silver halide developable.
- a direct positive emulsion can be employed to obtain a positive image.
- Development is followed by the conventional steps of bleaching, fixing, or bleach-fixing, to remove silver and silver halide, washing and drying.
- Couplers were dispersed and coated as follows.
- the test coupler (3.0 mmol), dissolved in half its weight of di-n-butyl phthalate and ethyl acetate (2.0g), was dispersed in aqueous gelatin (36g, 12.5%) using ultrasonic agitation.
- the gelatin solution contained a small amount (0.5%) of di-isopropyl-naphthalene sulphonic acid (sodium salt) as a surfactant.
- the resultant coupler dispersion was diluted to 200g with water and mixed with a green-sensitised silver chloride photographic emulsion (lOOg, 1.49% Ag, 4.5% gel). The mixture was spread on a resin-coated paper support to give a layer of the following composition:
- Gelatin l. ⁇ lg. ⁇ f 2 A protective gel supercoat containing hardener was applied to the coating.
- Sample strips of the coatings were exposed through a step tablet (density range 0-3, 0.15 increments) and developed in standard "KODAK" RA-4 process solutions.
- Sample strips from each coating were exposed and processed with RA4 chemistry within a few days of coating. Similar strips were put aside in a light-tight box and stored under ambient conditions for 29 weeks before exposure and processing.
- Couplers Ila and lib were examined as described in Example 1, except that the storage time was reduced to 17 weeks.
- Coupler R Fresh D.min Stored D.min Ila Me 0.11 0.20 lib t-Bu 0.10 0.12
- Couplers Ilia and Illb were dispersed with the stabilising compound IV in the following proportions:
- Coupler O.57mmole.m
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The use of 1H-pyrazolo[1,5-b]-1,2,4-triazole couplers containing a tertiary carbon group on the coupler nucleus in photographic silver halide materials of which the halide comprises more than 80 % chloride, in order to improve raw stock stability (shelf life).
Description
THE USE OF PYRAZOLO-TRIAZOLE PHOTOG APHTC COLOUR COUPLERS
This invention relates to the use of lH-pyrazolo[l,5-b]-l,2,4—triazole couplers in photographic materials. lH-Pyrazolo[1,5,-b]-l,2, -triazole couplers have been described in, for example, US Patent 4,621,046. In European Patent Specification 0,177,765 such a coupler having the formula:
Currently photographic colour paper processable in the RA4 process is comprised of silver halide emulsions having at least 80% silver chloride and preferably substantially pure silver chloride. Most lH—pyrazolo[l,5—b]—l,2,4—triazole couplers when incorporated into silver chloride emulsions provide photographic materials having poor raw stock keeping properties. That is, the material when stored after manufacture but before exposure and processing, shows 'significantly increased D . compared to freshly coated materials.
The present invention is directed to the use of certain 1H—pyrazolo[l,5—b]—1,2,4—triazole couplers in photographic silver chloride materials to improve their raw stock keeping properties.
Accordingly the present invention is directed to the use of lH-pyrazolo[l,5-b]-l,2,4- triazole couplers containing a tertiary carbon group on the coupler nucleus in photographic silver halide materials of which the halide comprises more than 80% chloride, in order to improve raw stock stability.
The present invention also provides a photographic material comprising a support bearing at least one photosensitive silver halide emulsion of which the halide is at least 80% molar chloride having in or adjacent the emulsion layer a lH-pyrazolo[l,5-b]-l,2,4—triazole coupler containing a tertiary carbon group on the coupler nucleus.
Preferably the silver halide emulsion comprises at least 90% silver chloride especially substantially pure silver chloride.
The preferred couplers have the formula
R2 R1 I " R3 \ / \ /
II I II N N N
wherein R 1 and R3 are each an alkyl or substituted alkyl group, and
R is a hydrogen or a coupling off group, at least one of R 1 and R3 comprising a group of the formula:
R ,4
- C -
wherein R4, R5 and R6 are individually a halogen atom or an alkyl, cycloakyl, amino, aryl, cyano, nitro, heterocyclic or — —R group wherein L is a linking group and R is an alkyl, aryl, heterocyclic group and
4 5 6 wherein any two of R , R and R can form a heterocyclic or alicyclic ring, any of the groups R 4, R5 and R6 being optionally substituted, all of the above groups and substituents being such that they do not adversely affect the desired properties of the coupler. In the above general formula when R 1 or R3 are a tertiary alkyl group they preferably contain 4-8 carbon atoms and may be t-butyl, t-pentyl or t—octyl. R 1 and R3 may otherwise contain 1—25 carbon atoms and may comprise a ballast group to render the coupler non—diffusible in photographic layers. Examples of R 4, R5 and R6 are chlorine, bromine and fluorine; alkyl groups containing 1 to 20 carbon atoms, for example, methyl, ethyl, propyl, butyl, pentyl, ethylhexyl and eicosyl; cyclohexyl and cyclopentyl; dioctylamino, dimethylamino and dodecylamino; aryl containing 6 to 20 carbon atoms, or example, phenyl, naphthyl and mesityl; cyano; nitro; a heterocyclic group comprised of atoms selected from carbon, oxygen, nitrogen and sulphur atoms necessary to complete a 5— or 6-membered ring, for example, pyrrolyl, oxazolyl and pyridyl. Examples of L are:
Examples of R are an alkyl containing 1 to 30 carbon atoms, for example, methyl, ethyl, propyl, butyl, pentyl and eicosyl; aryl, such as aryl containing 6 to 20 carbon atoms, for example, phenyl and napthyl; or a heterocyclic group, such as a 5- or 6—membered heterocyclic group comprised of atoms selected from carbon, nitrogen, oxygen and sulphur atoms, for example an oxazole, pyridine, pyrrole or thiophene ring. When any two of R 4, R5 and R6 form a heterocyclic ring this may be an oxazole, pyridine, pyrrole and thiophene; or when they form an alicyclic ring system, this may be cyclohexyl, norbornyl or adamantyl.
2 The coupling-off group R may be a halogen atom or an aryloxy or arylthio group.
The couplers used in the present invention may be prepared by methods known in the art. Typically, the couplers are associated with a silver halide emulsion layer coated on a support to form a photographic element. As used herein, the term "associated with" signifies that the coupler is incorporated in the silver halide emulsion layer or in a layer adjacent thereto where, during processing, it is capable of reacting with silver halide development products.
The photographic elements can be single colour elements or multicolour elements. In a multicolour element, the magenta dye-forming couplers of this invention would usually be associated with a
green—sensitive emulsion, although they could be associated with an emulsion sensitised to a different region of the spectrum, or with a panchromatically sensitised, orthochromatically sensitised or unsensitised emulsion. Multicolour elements contain dye image— orming units sensitive to each of the three primary regions of the spectrum. Each unit can be comprised of a single emulsion layer or of multiple emulsion layers sensitive to a given region of the spectrum. The layers of the element, including the layers of the image-forming units, can be arranged in various orders as known in the art.
A typical multicolour photographic element comprises a support bearing yellow, magenta and cyan dye image-forming units comprising at least one blue-, green- or red-sensitive silver halide emulsion layer having associated therewith at least one yellow, magenta or cyan dye-forming coupler respectively, at least one of the magenta dye-forming couplers being a coupler of this invention. The element can contain additional layers, such as filter and barrier layers.
In the following discussion of suitable materials for use in the emulsions and elements of this invention, reference will be made to Research Disclosure, December 1978, Item 17643, published by Industrial Opportunities Ltd., The Old Harbourmaster's, 8 North Street, Emsworth, Hants P010 7DD, U.K. This publication will be identified hereafter as "Research Disclosure".
The silver halide emulsion employed in the elements of this invention can be either negative-working or positive— orking. Suitable emulsions and their preparation are described in Research Disclosure Sections I and II and the publications cited therein. Suitable vehicles for
the emulsion layers and other layers of elements of this invention are described in Research Disclosure Section IX and the publications cited therein.
In addition to the couplers of this invention, the elements of the invention can include additional couplers as described in Research Disclosure Section VII, paragraphs D, E, F and G and the publications cited therein. The couplers of this invention and any additional couplers can be incorporated in the elements and emulsions as described in Research Disclosures of Section VII, paragraph C and the publications cited therein.
The photographic elements of this invention or individual layers thereof, can contain brighteners (see Research Disclosure Section V), antifoggants and stabilisers (see Research Disclosure Section VI), antistain agents and image dye stabiliser (see Research Disclosure Section VII, paragraphs I and J), light absorbing and scattering materials (see Research Disclosure Section VIII), hardeners (see Research Disclosure Section XI), plasticisers and lubricants (see Research Disclosure Section XII), antistatic agents (see Research Disclosure Section XIII), matting agents (see Research Disclosure Section XVI) and development modifiers (see Research Disclosure Section XXI).
The photographic elements can be coated on a variety of supports as described in Research Disclosure Section XVII and the references described therein.
Photographic elements can be exposed to actinic radiation, typically in the visible region of the spectrum, to form a latent image as described in Research Disclosure Section XVIII and then processed to form a visible dye image as described in Research Disclosure Section XIX. Processing to form a visible
dye image includes the step of contacting the element with a colour developing agent to reduce developable silver halide and oxidise the colour developing agent. Oxidised colour developing agent in turn reacts with the coupler to yield a dye.
Preferred colour developing agents are p-phenylene diamines. Especially preferred are 4—amino-3—meth l— ,N—diethylaniline hydrochloride, 4-amino-3-meth l-N-ethyl-N-β-(methanesulphonamido)- ethylaniline sulphate hydrate, 4—amino—3—methyl—N— ethyl-N-β-hydroxyethylaniline sulphate, 4-amino- 3-β-(methanesulphonamido)eth l-N,N-diethylaniline hydrochloride and 4-amino-N-ethyl-N-(2-methoxy- eth l)-m-toluidine di-p-toluene sulphonate. With negative-working silver halide emulsions this processing step leads to a negative image. To obtain a positive (or reversal) image, this step can be preceded by development with a non-chromogenic developing agent to develop exposed silver halide, but not form dye, and then uniform fogging of the element to render unexposed silver halide developable. Alternatively, a direct positive emulsion can be employed to obtain a positive image. Development is followed by the conventional steps of bleaching, fixing, or bleach-fixing, to remove silver and silver halide, washing and drying.
The following examples are included for a better understanding of the invention. EXAMPLE 1 Couplers were dispersed and coated as follows. The test coupler (3.0 mmol), dissolved in half its weight of di-n-butyl phthalate and ethyl acetate (2.0g), was dispersed in aqueous gelatin (36g, 12.5%) using ultrasonic agitation. The gelatin solution contained a small amount (0.5%) of di-isopropyl-naphthalene sulphonic acid (sodium salt)
as a surfactant. The resultant coupler dispersion was diluted to 200g with water and mixed with a green-sensitised silver chloride photographic emulsion (lOOg, 1.49% Ag, 4.5% gel). The mixture was spread on a resin-coated paper support to give a layer of the following composition:
Ag 0.267g.m~2
__2 Coupler O.54mmol.m
Gelatin l.βlg.πf2 A protective gel supercoat containing hardener was applied to the coating.
Sample strips of the coatings were exposed through a step tablet (density range 0-3, 0.15 increments) and developed in standard "KODAK" RA-4 process solutions.
Sample strips from each coating were exposed and processed with RA4 chemistry within a few days of coating. Similar strips were put aside in a light-tight box and stored under ambient conditions for 29 weeks before exposure and processing.
The sensitometric parameters of the two sets of coatings were measured. It was observed that the stored coatings showed significantly higher Dmin values than the freshly processed coatings. However, the increase in Dmin was much smaller for the 6—t—Bu substituted examples lb and Id than for their analogous 6—Me couplers,la and Ic. (See Table below)
Cl H
R -ft Λ.Λ ■lrl (CH2)3- / — NH-Ball (I)
N- -Ji¬ -N
Fresh Stored
Coupler Ball Dmin Dmin
la Me ) (n -?12H25 /fc-Bu 0.12 0.21
) lb t-Bu) COCHO y - OH 0.11 0.15
EXAMPLE 2
Couplers Ila and lib were examined as described in Example 1, except that the storage time was reduced to 17 weeks. The sensitometric data shown below confirmed the advantage of the 6-t—Bu substituent.
(II) 7(t
Coupler R Fresh D.min Stored D.min Ila Me 0.11 0.20 lib t-Bu 0.10 0.12
Couplers Ilia and Illb were dispersed with the stabilising compound IV in the following proportions:
Coupler 2
Stabiliser 1
Solvent 3
(dibutyl phthalate)
Me Me
The dispersions were coated with a green sensitive silver chloride emulsion so as to give the following coverages: Coupler: O.57mmole.m
Silver: 2.4mmole.m _2
One pair of sample strips from each coating was incubated for 7 days at 50°C, 50%RH in the dark for comparison with an identical pair stored at ambient temperature. Both pairs were step wedge exposed and processed (RX4). The sensitometric data shown below show that the strips stored at elevated temperature showed a much greater Dmin than those stored at room temperature, but the difference was dramatically lower for the 6—t-Bu example (Illb) than for Ilia.
I I I
Coupler R ΔDmin (inc - fresh)
Ilia Me +1.39
Illb t-Bu +0.28
Claims
1. The use of lH-pyrazolo[l,5-b]-l,2,4-triazole couplers containing a tertiary carbon group on the coupler nucleus in photographic silver halide ' materials of which the halide comprises more than 80% chloride, in order to improve raw stock stability.
2. A photographic material comprising a support bearing at least one photosensitive silver halide emulsion of which the halide is at least 80% molar chloride having in or adjacent the emulsion layer a lH-pyrazolo[l,5-b]-l,2,4-tr"iazole coupler containing a tertiary carbon group on the coupler nucleus.
3. The invention as claimed in Claim 1 or 2 in which the coupler has the formula:
wherein R 1 and R3 are each an alkyl or substituted alkyl group, and
2 R is a hydrogen or a coupling off group, ζ 1 3 at least one of R and R comprising a tertiary carbon group of the formula:
0 - C - 
wherein R 4, R5 and R6 are individually a halogen atom 5 or an alkyl, cycloakyl, amino, aryl, cyano, nitro, heterocyclic or -L-R group wherein L is a linking group and
R is an alkyl, aryl, heterocyclic group and wherein any two of R4, R5 and R6 can form a heterocyclic or alicyclic ring, any of the groups R 4, R5 and R6 being optionally substituted, all of the above groups and substituents being such that they do not adversely affect the desired properties of the coupler.
4. The invention as claimed in Claim 3 in which R or R is a tertiary alkyl group containing 4-8 carbon atoms.
5. The invention as claimed in any of Claims 1—4 in which the coupler comprises a coupling—off group which is a halogen atom or an aryloxy or arylthio group.
6. The invention as claimed in any of Claims 1-5 in which the emulsion is substantially pure silver chloride.
7. A photographic material as claimed in any of Claims 2—6 which is a multicolour material comprising a support bearing yellow, magenta and cyan dye image—forming units comprising at least one blue-, green- or red—sensitive silver halide emulsion layer having associated therewith at least one yellow, magenta or cyan dye—forming coupler respectively, at least one of the magenta dye-forming couplers being a coupler as defined in any of Claims 2—5.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE69027309T DE69027309D1 (en) | 1989-02-22 | 1990-02-14 | USE OF PYRAZOLTRIAZOLE PHOTOGRAPHIC COLOR COUPLER |
| EP90903197A EP0460008B1 (en) | 1989-02-22 | 1990-02-14 | The use of pyrazolo-triazole photographic colour couplers |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB898904004A GB8904004D0 (en) | 1989-02-22 | 1989-02-22 | The use of pyrazolo-triazole photographic colour couplers |
| GB8904004.2 | 1989-02-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1990010253A1 true WO1990010253A1 (en) | 1990-09-07 |
Family
ID=10652100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/GB1990/000232 Ceased WO1990010253A1 (en) | 1989-02-22 | 1990-02-14 | The use of pyrazolo-triazole photographic colour couplers |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0460008B1 (en) |
| JP (1) | JPH0354554A (en) |
| AT (1) | ATE139043T1 (en) |
| DE (1) | DE69027309D1 (en) |
| GB (1) | GB8904004D0 (en) |
| WO (1) | WO1990010253A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992010788A1 (en) * | 1990-12-06 | 1992-06-25 | Kodak Limited | Photographic colour couplers and photographic materials containing them |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0273712A2 (en) * | 1986-12-27 | 1988-07-06 | Konica Corporation | Light-sensitive silver halide photographic material |
| US4766057A (en) * | 1986-09-04 | 1988-08-23 | Fuji Photo Film Co., Ltd. | Method of forming a color image |
| EP0325276A2 (en) * | 1988-01-21 | 1989-07-26 | Fuji Photo Film Co., Ltd. | Method for processing silver halide color photographic material |
| EP0326406A2 (en) * | 1988-01-28 | 1989-08-02 | Konica Corporation | Silver halide photographic light-sensitive material |
-
1989
- 1989-02-22 GB GB898904004A patent/GB8904004D0/en active Pending
-
1990
- 1990-02-14 AT AT90903197T patent/ATE139043T1/en not_active IP Right Cessation
- 1990-02-14 DE DE69027309T patent/DE69027309D1/en not_active Expired - Lifetime
- 1990-02-14 WO PCT/GB1990/000232 patent/WO1990010253A1/en not_active Ceased
- 1990-02-14 EP EP90903197A patent/EP0460008B1/en not_active Expired - Lifetime
- 1990-02-20 JP JP2037537A patent/JPH0354554A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4766057A (en) * | 1986-09-04 | 1988-08-23 | Fuji Photo Film Co., Ltd. | Method of forming a color image |
| EP0273712A2 (en) * | 1986-12-27 | 1988-07-06 | Konica Corporation | Light-sensitive silver halide photographic material |
| EP0325276A2 (en) * | 1988-01-21 | 1989-07-26 | Fuji Photo Film Co., Ltd. | Method for processing silver halide color photographic material |
| EP0326406A2 (en) * | 1988-01-28 | 1989-08-02 | Konica Corporation | Silver halide photographic light-sensitive material |
Non-Patent Citations (1)
| Title |
|---|
| Derwent's abstract, No 87-339618/48, JP 62246054, publ. week 8748, Dialog Information Service, file 351, WPI & JP-A-62246054 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992010788A1 (en) * | 1990-12-06 | 1992-06-25 | Kodak Limited | Photographic colour couplers and photographic materials containing them |
| US5374511A (en) * | 1990-12-06 | 1994-12-20 | Eastman Kodak Company | Photographic color couplers and photographic materials containing them |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8904004D0 (en) | 1989-04-05 |
| DE69027309D1 (en) | 1996-07-11 |
| EP0460008A1 (en) | 1991-12-11 |
| EP0460008B1 (en) | 1996-06-05 |
| JPH0354554A (en) | 1991-03-08 |
| ATE139043T1 (en) | 1996-06-15 |
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