EP0463136A1 - Photographic silver chloride emulsions. - Google Patents
Photographic silver chloride emulsions.Info
- Publication number
- EP0463136A1 EP0463136A1 EP91901765A EP91901765A EP0463136A1 EP 0463136 A1 EP0463136 A1 EP 0463136A1 EP 91901765 A EP91901765 A EP 91901765A EP 91901765 A EP91901765 A EP 91901765A EP 0463136 A1 EP0463136 A1 EP 0463136A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- silver chloride
- emulsion
- coupler
- photosensitive
- bisphenol derivative
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- 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
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
-
- 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
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/035—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein characterised by the crystal form or composition, e.g. mixed grain
-
- 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
-
- 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
- G03C7/3022—Materials with specific emulsion characteristics, e.g. thickness of the layers, silver content, shape of AgX grains
-
- 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
- G03C7/392—Additives
- G03C7/39208—Organic compounds
- G03C7/39212—Carbocyclic
- G03C7/39216—Carbocyclic with OH groups
Definitions
- This invention relates to photographic silver chloride emulsions having improved keeping properties.
- Photographic silver chloride emulsions are now widely used in the manufacture of photographic colour negative paper materials. As such materials age their sensitometric performance changes such that the speed and minimum density (D min ) increase while their contrast decreases.
- D min speed and minimum density
- Known techniques for countering these defects in silver halide emulsions in general include the method described in British
- Specification 1 262 127 which comprises the addition of small quantities of reducing agents such as amino- hexose-reductones. Control of the emulsion pH and pAg can also be beneficial.
- a photosensitive silver chloride emulsion comprising at least 90% silver chloride whose keeping properties have been improved by the incorporation therein of a bisphenol derivative having two linked phenol rings wherein the hydrogen atom of one of the phenolic hydroxy groups is replaced by a blocking group which is a substituent other than hydrogen and at least one of the phenol rings is substituted.
- the blocking group may be any group which does not affect the desired properties of the
- the two phenol rings of the stabilizer may be linked directly by a single bond or indirectly by a linking group.
- the link between the phenol rings is ortho relative to the phenolic hydroxy group of one ring and the blocked phenolic hydroxy group of the other ring.
- each phenol ring independently is substituted in a position ortho or para relative to the unblocked or blocked phenolic hydroxy groups. It is further preferred that substituents are present in both ortho and para positions.
- the bis-phenol compound preferably has the general formula:
- R is alkyl, cycloalkyl, alkenyl, aryl, acyl, alkylsuphonyl or arylsulphonyl,
- R 1 is a single bond or a linking group selected from alkylene, alkylidene, a heteroatom or sulphonyl, and
- each R 2 independently represents one or more substituents each selected from alkyl, alkoxy, alkenyl, cycloalkyl, aryl or aryloxy or, each R independently represents the atoms necessary to complete with the benzene ring to which it is
- blocking group R are methyl, ethyl, propyl or butyl, cyclohexyl, phenyl, acetyl or benzoyl.
- linking group R 1 examples are methylene, butylidene, 3,5,5,-trimethylhexylidene, oxygen, sulphur or sulphonyl.
- An especially preferred group of bis-phenol compounds has the general formula:
- R 1 and R are as defined above, and
- R 3 , R 4 , R 5 and R 6 are each
- R 3 and R 4 are identical and R 5 and R 6 are identical.
- the blocked bisphenol derivatives are readily prepared from their unblocked counterparts, many of which are commercially available.
- a blocking group may be introduced into the unblocked parent bisphenol by reaction with an appropriate reactive halogen-containing compound e.g. an alkyl bromide, acyl chloride, sulphonyl chloride or a dialkyl sulphate e.g. diethyl sulphate.
- unblocked parent bisphenols from which the stabilizers of the present invention may be prepared are as follows:
- the present invention also provides a method for improving the keeping properties of a silver chloride emulsion comprising the incorporation therein of a bisphenol derivative having two linked phenol rings wherein the hydrogen atom of one of the phenolic hydroxy groups is .replaced by a blocking group which is a substituent other than hydrogen and at least one of the phenol rings is substituted.
- the present invention further provides a photographic material comprising a support bearing a layer of a photosensitive silver chloride emulsion said material having incorporated therein a bisphenol derivative having two linked phenol rings wherein the hydrogen atom of one of the phenolic hydroxy groups is replaced by a blocking group which is a substituent other than hydrogen and at least one of the phenol rings is substituted in order to improve its keeping properties.
- the silver chloride emulsions used in the present invention contain more than 90 mole %, silver chloride preferably the emulsions are substantially pure silver chloride.
- the bis-phenol compounds may be incorporated in the silver chloride emulsions as a dispersion of droplets of a high boiling coupler solvent containing the bis-phenol. Such droplets may also contain a colour coupler. Alternatively they may be
- the colour coupler may be of any class of couplers useful in colour photographic materials.
- coupler classes include phenolic and naphtholic cyan couplers, pyrazolidone and
- Such couplers preferably have the general formula:
- R 7 represents one or more substituents of
- R 8 is a coupliig-off group, preferably an aryloxy group.
- the fourth dispersion contained a comparison material the bis-phosphate ester of the formula:
- Dispersions of each coupler alone were also made.
- the coupler was dissolved in its own weight of ethyl acetate and one half its weight of dibutyl phthalate. When present the bisphenol was included at half the weight of the coupler.
- the oil solutions were dispersed in aqueous gelatin using ultrasonic agitation as in Example 1.
- Coupler (B) Each dispersion containing Coupler (B) was mixed with a red-sensitised silver chloride emulsion and coated on a resin-coated paper support, such that the silver and coupler coverages were, respectively,
- coatings was made from the dispersions at the same component coverages but utilising a blue-sensitised emulsion (as used in Example 1) in place of the red sensitised emulsion.
- Coupler (C) was coated together with a green sensitised silver
- chloride emulsion at silver and coupler coverages of 285 mg/m2 and 447 mg/m2 respectively.
- Sample strips of the fresh coatings were exposed and processed through RA4 chemistry to assess sensitometric performance. Another strip from each coating was incubated in the dark for 8 days at 50°C and 50% RH before being exposed and processed.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
On décrit une émulsion photographique de chlorure d'argent, comportant au moins 90 % de chlorure d'argent et dont les caractéristiques de stockage ont été améliorées par l'incorporation d'un dérivé de bisphénol à deux anneaux de phénol liés. L'atome d'hydrogène de l'un des groupes hydroxy phénoliques est remplacé par un groupe de blocage, qui est un substituant autre qu'hydrogène, et au moins un des anneaux de phénol est substitué.A photographic silver chloride emulsion comprising at least 90% silver chloride is described, the storage characteristics of which have been improved by the incorporation of a bisphenol derivative with two linked phenol rings. The hydrogen atom of one of the phenolic hydroxy groups is replaced by a blocking group, which is a substituent other than hydrogen, and at least one of the phenol rings is substituted.
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB909001078A GB9001078D0 (en) | 1990-01-17 | 1990-01-17 | Photographic silver chloride emulsions |
GB9001078 | 1990-01-17 | ||
PCT/EP1991/000069 WO1991010938A1 (en) | 1990-01-17 | 1991-01-12 | Photographic silver chloride emulsions |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0463136A1 true EP0463136A1 (en) | 1992-01-02 |
EP0463136B1 EP0463136B1 (en) | 1995-12-27 |
Family
ID=10669458
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP91901765A Expired - Lifetime EP0463136B1 (en) | 1990-01-17 | 1991-01-12 | Photographic silver chloride emulsions |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0463136B1 (en) |
JP (1) | JPH04506579A (en) |
DE (1) | DE69115767T2 (en) |
GB (1) | GB9001078D0 (en) |
WO (1) | WO1991010938A1 (en) |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1313964C (en) * | 1988-03-30 | 1993-03-02 | Merle W. North | Apparatus for forming a web |
GB8927563D0 (en) * | 1989-12-06 | 1990-02-07 | Kodak Ltd | Photographic silver halide materials |
-
1990
- 1990-01-17 GB GB909001078A patent/GB9001078D0/en active Pending
-
1991
- 1991-01-12 JP JP50223492A patent/JPH04506579A/en active Pending
- 1991-01-12 WO PCT/EP1991/000069 patent/WO1991010938A1/en active IP Right Grant
- 1991-01-12 DE DE69115767T patent/DE69115767T2/en not_active Expired - Fee Related
- 1991-01-12 EP EP91901765A patent/EP0463136B1/en not_active Expired - Lifetime
Non-Patent Citations (1)
Title |
---|
See references of WO9110938A1 * |
Also Published As
Publication number | Publication date |
---|---|
WO1991010938A1 (en) | 1991-07-25 |
DE69115767T2 (en) | 1997-02-06 |
EP0463136B1 (en) | 1995-12-27 |
GB9001078D0 (en) | 1990-03-14 |
DE69115767D1 (en) | 1996-02-08 |
JPH04506579A (en) | 1992-11-12 |
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