GB2032914A - Heterocyclyl-substituted phenacyl thioether derivatives for use as photographic development inhibitors - Google Patents
Heterocyclyl-substituted phenacyl thioether derivatives for use as photographic development inhibitors Download PDFInfo
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- GB2032914A GB2032914A GB7831402A GB7831402A GB2032914A GB 2032914 A GB2032914 A GB 2032914A GB 7831402 A GB7831402 A GB 7831402A GB 7831402 A GB7831402 A GB 7831402A GB 2032914 A GB2032914 A GB 2032914A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
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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
- G03C7/305—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers
- G03C7/30511—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers characterised by the releasing group
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- General Physics & Mathematics (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Novel photographic development inhibitor compounds are described which couple with an oxidised colour developer to yield a colourless compound and to release a development inhibiting compound. These compounds are of the formula <IMAGE> wherein R1 is a substituted phenyl group which comprises a ballasting alkyl group, R2 represents the atoms necessary to complete a five or six membered heterocyclic ring system which may be further substituted and R3 is an aryl, or heterocyclic radical, any of which ring systems may be further substituted, the group -S-R3 being a development inhibiting group. These compounds exhibit high reactivity. The preparation of these compounds and their use in photographic material is also described.
Description
SPECIFICATION
Chemical compounds
This invention relates to novel chemical compounds and to their use as development inhibitor releasing compounds in photographic material. Development inhibitor releasing compounds are hereinafter referred to as D.l.R. compounds.
According to the present invention there are provided compounds of the general formula I:
wherein R1 is a substituted phenyl group which comprises a ballasting alkyl group, R2 represents the atoms necessary to complete a five or six membered heterocyclic ring system which may be further substituted and R3 is an aryl, or heterocyclic radical, any of which ring systems may be further substituted, the group~S~R3 being a development inhibiting group.
By ballasting alkyl group is meant a straight or branched chain alkyl group, optionally substituted, having at least 10 carbon atoms. The presence of the ballasting alkyl group in the D.l.R. compound renders this compound substantive to the layer in which it is coated.
Compounds of the above formula I may be prepared by reacting a solution of a compound of the general formula Il:-
with a solution of a compound of formula Ill
where R, and R2 have the meanings assigned to them above in the presence of a base, reacting a solution of the resultant compound of the formula IV:
with halogen to form a compound of the formula V:
where A is a halogen atom and reacting the solution of compound V with a compound M-S-P3 where R3 has the meaning assigned to it above and M is an alkali metal.
Preferably in steps 1 and 3 of the above process the solvent is acetonitrile.
Preferably the base used in the first step is triethylamine. Preferably the halogen used in the second step is bromine. Preferably M is potassium.
According to another aspect of the present invention there is provided a light-sensitive photographic material which comprises, coated on a photobase. at least one silver halide emulsion layer, the said emulsion layer or a layer adjacent thereto comprising a compound of the general formula #.
Preferably the compound of formula I is present in the silver halide emulsion layer.
In the compounds of formula I both the group
and the group
which are attached to the central methine group of the compound are electron withdrawing groups.
This means that the methine group is an activated methine group which can couple with oxidised colour developers of the para-phenylene diamine type in the same way as colour couplers couple with such oxidised colour developers. The coupling of the compound of formula I with oxidised colour developer leads to an unstable compound in which elimination occurs and the group R3~S3 is released.
The compound H~S~R3 is a D.I. compound. The use of compounds which release D.l.
compounds imagewise is well known in the photographic art to produce useful inter-layer and intralayer effects.
While various development inhibitor-releasing compounds have been produced hitherto the majority of these compounds are not completely satisfactory. For example in the case of a development inhibitor releasing compound which forms a dye upon colour development, the colour coupler residue of the D.l.R. compound must be carefully selected to achieve the correct colour balance in the photographic colour image because of the specific absorption properties required of the resulting dye. It has proved difficult to produce useful D.l.R. colour couplers.
On the other hand those development inhibitor releasing compounds which form no dye with the oxidation products of a colour development agent either possess extremely low reactivity or cause serious speed losses during development.
However the compounds of the present invention form colourless compounds when reacted with the oxidation products of the colour developing agent. The colourless residue does not constitute any part of the resulting image. This has the advantage that the novel releasing compounds can be applied to any required layer in the photographic material. Furthermore, the compounds of the present invention have an extremely high reactivity with the oxidation products of the colour developing agent.
Consequently only small quantities of compound are required to produce excellent intra-image and inter-image effects without serious speed losses.
In yet another aspect of the present invention there is provided a process for the production of a photographic image which comprises imagewise exposing a light-sensitive photographic silver halide material which comprises in at least one silver halide layer or a layer adjacent thereto a compound of formula I and developing the exposed silver halide with a paraphenyiene diamine colour developing agent thereby to liberate imagewise the group R3~S.
Suitable S~R3 groups are members of the mercapto pyrimidine series, members of the mercapto thiadiazole series such as a 2-mercapto thiadiazolotriazine, members of the mercapto triazine series, members of the mercapto tetrazole series, or members of the mercapto triazole series, or an optionally substituted mercapto benzene, of which the substituents may be for example carboxyl, nitro or acylated amino groups, such as 1-mercapto-2-benzoic acid, 1-mercapto-2-nitrobenzene, or 1-mercapto-3- heptadecanoylamino benzene.
Preferably R3 is a phenyl substituted tetrazole group.
Preferably R2 represents the atoms necessary to complete an optionally substituted triazole, tetrazole, pyrazole or imidazole ring system. Examples of substituents which may be present in the ring system are alkyl groups and substituted alkyl groups such as sulphoalkyl groups.
Particularly useful groups R, are those of the general formula VI:
where R4 is a ballasting alkyl group or comprises a ballasting alkyl group.
Other useful groups R, are those of the formula VIII:-
where L is )an 502 or -CO- link and R4 is as just defined.
The D.I.R. compounds of the present invention may be used in any photograp < product which can be processed by a chromogenic process and in which increased image sharpne 3nd/or interlayer effects are desired. Thus the greatest use of D.l.R. compounds of the present inven z is expected to be in the field of colour photographic material and in particular in colour negative fi naterial. When used in colour film material it is expected that the D.l.R. compounds of the present invention will be present in colour-sensitised silver halide emulsion layers which comprise at least one colour developer.
Useful amounts of D.l.R. present in such silver halide emulsion layers are 5-10 mole % of the colour coupler present.
Examples of specific compounds according to the present invention which release a development inhibitor compound on coupling are:~ Compound 1.
Compound 2.
Compound 3.
Compound 4.
Compound 5.
Compound 6.
Compound 7.
Compound 8.
Compound 9.
Compound 10.
Compound 11.
Compound 12.
The following Examples will serve to illustrate the invention:~
EXAMPLE 1
Preparation of compound 1 a) -(Tetrazolyl)-o-tetradecyWoxyacetophenone To a solution of o-tetradecyloxyphenacylbromide (1 6.4 g) in acetonitrile (75 ml) was added a solution of tetrazole (2.8 g) and triethylamine (4.0 g) in acetonitrile (75 ml). The reaction mixture was stirred at reflux temperature for 2 hours then evaporated to dryness. The residue was dissolved in chloroform and the organic layer washed with water, dried over MgS04, filtered and evaporated to give the crude compound. Recrystallisation from petrol 60--800 gave the acetophenone derivative as a fine white powder (12. 7 g) m.p. 67--690.
b) #-Brnmo-a'-tetrazolyl-o-tetradecyloxyacetophenone To the above acetophenone derivative (10.8 g) in chloroform (150 ml) maintained at 500 was added dropwise a solution of bromine (4.5 g 1.5 ml) in chloroform (50 ml). The reaction mixture was stirred for a further hour at 500 and then evaporated. The residue was recrystallised from petrol 60~80 to afford the #-brnmo derivative as a fine white powder (10.5 g) m.p. 39#41C.
c) α-Tetrazolyl-α-[1-phenyltetrazole]-5-thiyl- -o-tetradecyloxyacetophenone (compound 1)
A mixture of the above bromo derivative (6.0 g) and the potassium salt of 1-phenyl-5-thiotetrazole (2.75 g) in acetophenone (45 ml) was stirred at reflux temperature for 2 hours. The reaction mixture was cooled, filtered and evaporated. The residue was recrystallised from methanol to give compound 1 as a white powder (5.1 g) m.p. 60#61C. (Found: C, 62.44: H, 7.07; N, 19.1%. C30H40N802S requires: C, 62.47; H, 6.98; N, 19.42%).
EXAMPLE 2
Preparation of compound 3 a) a-3(5)-Heptylthiotriazolyl-o-tetradecyloxyacetophenone
A solution of o-tetradecyloxyphenacyl bromide (lOg) in warm acetonitrile (30 ml) was added to a solution of 3(5)-heptylthiotriazole (6 g) and triethylamine (3.0 g) in acetonitrile (20 ml). The reaction mixture was stirred at room temperature for 6 hours and then evaporated. The residue was dissolved in ethyl acetate (50 ml) and the organic layer washed with water (2 x 50 ml), dried over MgSO4, filtered and evaporated. Recrystallisation of the residue from methanol gave the acetophenone derivative as an off-white powder (7.8 g) m.p. 61-62 .
b) α-Bromo--o-tetradecyloxyacetophenone To a stirred solution of the above derivative (5.1 g) in chloroform (75 ml) at 60C was added over a
period of 2 hours a solution of bromine (1.6 g) in chloroform (10 ml). The reaction mixture was stirred at
reflux temperature for a further 2 hours and then evaporated. Trituration of the residual oil in methanol
at 0 afforded the product in solid form. Subsequent filtration gave the iu-bromo derivative as an off
white powder (5.4 g) m.p. 45~46 .
c) α[3(5)-Heptylthiotriazolyl]-α-[1-phenyltetrazole-5-thiyl]-o-tetradecyloxyacetophenone (compound
3)
The above bromo-derivative (5.0 g) and the potassium salt of 1-phenyl-5-thiotetrazole (1.8 g)
were stirred in acetonitrile (35 ml) at gentle reflux for 2 hours. The reaction mixture was cooled to room temperature, filtered and evaporated. Recrystallisation of the residue from methanol gave compound 3
as a pure white powder (4.1 g) m.p. 68~70 . (Found: C, 64.67; H, 7.1; N, 13.91%. C36H55N702S2 requires: C, 64.74; H, 7.72; N, 13.91%).
EXAMPLE 3
Preparation of compound 5
a) α-[3(5)-Heptylthiotriazolyl]-p-hexadecylamidoacetophenone
A mixture of p-hexadecylamidophenacyl bromide (11.7 g) and the potassium salt of 3(5)
heptylthiotriazole (6.0 g) in 30 ml acetonitrile was stirred at reflux temperature for 2 2 hours. The
reaction mixture was cooled, filtered and evaporated. The residue was recrystallised from methanol to
give a fine white solid (12.4 g) m.p. 110#1120.
b) cu-Bromo-cY- [ 3(5)-heptylthiotriazolyl ] -p To the above acetophenone derivative (8.0 g) in chloroform (100 ml) was added a solution of bromine (2.4 g, 0.8 ml) in chloroform (50 ml). The reaction mixture was stirred at room temperature for 4 hours and evaporated to give the -brnmo-denvative as a colourless viscous oil (9.0 g).
c) α[3(5)-Heptylthiotriazolyl]-α-[1-phenyltetrazole-5-thiyl]-p-hexadecylamidoacetophenone (compound 5)
The above bromo-derivative (4.4 g) and the potassium salt of 1-phenyl-5-thiotetrazole (1.6 g) were stirred in acetonitrile (50 ml) at reflux temperature for 1 hour. The reaction mixture was cooled, filtered and evaporated. The product was purified by column chromatography on silica gel to give compound 5 as a waxy solid (3.4 g). (Found: C, 64.66; H, 8.17; N, 14.77%. C40H58H8O2S2 requires: C, 64.36; H, 7.83; N, 15.00%).
EXAMPLE 4
Preparation of compound 10 α-[2-Mercaptobenzthiazolyl]-α-[tetrazolyl]-o-tetradecyloxyacetophenone (compound 10)
A solution of a-bromo-a-tetrazolyl-o-tetradecyloxyacetophenone (4.79 g) and the potassium salt of 2-mercaptobenzthiazole (2.1 g) in acetonitrile (50 ml) was stirred at reflux for 10 hours. The reaction mixture was evaporated, the residue dissolved in ethyl acetate (50 ml) and the organic layer washed with water (3 x 50 ml), dried over Na2SO4, filtered and evaporated. Chromatography on silica gel and recrystallisation from methanol gave a light yellow powder (3.1 g) m.p. 49--500. (Found: C, 63.61; H, 6.84; N, 12.48%. C30H39N5O2S2 requires: C, 63.72; H, 6.90; N, 12.39%).
EXAMPLE 5
Preparation of compound 11 α-[4-Nitrophenylthio]-α-[tetrazolyl]-o-tetradecyloxyacetophenone (compound 11)
A solution of α-bromo-α-tetrazolyl-o-tetradecyloxyacetophenone (4.79 g) and the potassium salt of 4-nitrothiophenol (2.0 g) in acetonitrile (50 ml) was stirred at reflux for 2 hours. The reaction mixture was evaporated and the residue dissolved in chloroform, washed with water (3 x 50 ml), dried over Na2SO4, filtered and evaporated. Chromatography on silica gel and recrystallisation from methanol gave compound 1 1 as a light yellow powder (2.1 g) m.p. 52#53C. (Found: C, 63.05; H, 7.09; N, 12.49%.
C29H39N5O4S requires: C, 62.93; H, 7.05; N, 12.66%).
EXAMPLE 6
Use example - development inhibition
1 -(2,4,6-Trichlorophenyl)-3-(3-[(2,4-ditetramylphenoxy)acetamido]benzamido)-5-pyrazolone ( 1 0 g) was dissolved in a solution of tricresylphosphate (10 g) and ethyl acetate (10 g). A solution of gelatin (80 g) was added followed by water (20 ml) and a wetting agent (10% Nekal BX solution (20 ml). The whole was then dispersed using an ultrasonic mixer.
The above coupler emulsion (25 g) was added to a silver iodo-bromide emulsion (40 g) having a silver content of 4.9 g and an average iodide content of 8.8 molar per cent. Gelatin solution (48 g, 10%
DCB) and further wetting agent (10% Nekal BX solution, 3.8 ml) was added and the whole made up to 200 g with water.
The mixture was coated onto subbed triacetate film base to give a silver coating weight of 20 mg.
per dm2 and a coupler coating weight of 6.4 mg. per dm2. Above this was coated a 20 mg per dm2 gelatin layer containing a triazine hardener.
The coating was exposed to a continuous wedge and then subjected to the following processing sequence at 37.8 C.
1. Colour development .............. 3.25 mins.
2. Bleach ................... ................... 6.50 mins.
3. Wash . ......... 3.25 mins.
4. Fix . ..... ..... .. 6.50 mins.
5. Wash .. ........................... ................... ........ 3.25 mins.
6. Stabilize .. ................ .. 1.50 mins.
The processing baths had the following compositions:
1. Developer
Potassium carbonate 37.5 g
Sodium metabisulphite (anhyd) 4.25 g
Potassium iodide 2.9 g
Sodium bromide 1.3 g
Hydroxylamine sulphate 2.0 g
4-(N-ethyl-N-ss-hydroxyethylamino)-
2-methylaniline sulphate
Water to 1 litre
2. Bleach
Ammonium bromide 150 g
Ferric ammonium ethylenediamine
tetracetic acid 175 ml
Glacial acetic acid 10.5 ml
Sodium nitrate 35 g
Water to 1 litre
4. Fix
Ammonium thiosulphate (50%) 162 ml
Diethylene triamine penta-acetic acid 1.25 g
Sodium metabisulphite (anhyd) 12.4 g
Sodium hydroxide 2.4 9 Water to 1 litre
6.Stabiliser
35% formaldehyde solution 5.0 ml
Water to 1 litre
The above procedure (CONTROL) produced the following photographic results for maximum contrast (yam) and contrast adjusted speed (#y/4):- Control rm y/4 (log E units)
Pyrazolone coupler alone 1.19 2.74
To allow for the effect of contrast on foot speed the sty/4 value has been quoted. This is defined as: sty/4 = (Speed at a density level of fog) + y/4
The above coating procedure was then repeated but in addition to the pyrazolone coupler, coatings were made which individually incorporated 5, 10 or 20 mole per cent of the D.l.R. compounds, and the percentage ym suppression and change in Sy/4 compared with the control were measured.
TABLE I
%#m Change in .DIR Compound Suppression sty/4 5% Level of Compound 1 59 + 0.15 10% Level of Compound 1 72 +0.14 5% Level of Compound 3 37 + 0.08 10% Level of Compound 3 52 + 0.12 5% Level of Compound 4 71 + 0.15 10% Level of Compound 4 82 + 0.18 10% Level of Compound A 6 - 0.20 20% Level of Compound A 17 - 0.21 5% Level of Compound B 32 - 0.09 10% Level of Compound B 42 - - 0.13 The D.l.R. compound A has the following structure
and is claimed in British Patent 1,224,555.
The D.l.R. compound B has the following structure:-
and is claimed in United States Patent 3,928,041.
Table 1 clearly shows that the compounds of the current case are significantly more active (i.e.
they exhibit greater development inhibition) as shown by the high y max suppression values compared with those of the known D.l.R. compounds A and B.
Furthermore the D.l.R. compounds of the current case show no speed loss as shown by the positive sty/4 values, compared with the known D.l.R. compounds A and B.
Claims (13)
1. Compounds of the general formula
wherein Rt is a substituted phenyl group which comprises a ballasting alkyl group, R2 represents the atoms necessary to complete a five or six membered heterocylic ring system which may be further substituted and R3 is an aryl, or heterocyclic radical, any of which ring systems may be further substituted, the group --SS-R, being a development inhibiting group.
2. A compound which is one of the compounds 1 to 1 2 hereinbefore set forth.
3. A process for the preparation of a compound of formula I set forth in claim 1 which comprises reacting a compound of formula II:
with a solution of a compound of formula Ill:-
where Rr and R2 have the meanings assigned to them in claim 1 in the presence of a base, reacting a solution of the resultant compound of formula IV:
with halogen to form a compound of formula V:
where A is a halogen atom and reacting the solution of compound V with a compound M-S-R3 where R3 has the meaning assigned to it in claim 1 and M is an alkali metal.
4. A process according to claim 3 wherein the solvent used in steps 1 and 3 is acetonitrile.
5. A process according to claim 3 or claim 4 wherein the base used in step 1 is triethylamine.
6. A light-sensitive photographic material which comprises, coated on a photobase, at least one silver halide emulsion layer, the said emulsion layer or a layer adjacent thereto comprising a compound of the general formula I as defined in claim 1 or a compound as claimed in claim 2.
7. A light-sensitive photographic material according to claim 6 wherein the compound of formula I or the compound as claimed in claim 2 is present in the silver halide emulsion layer.
8. A process for the production of a photographic image which comprises imagewise exposing a light-sensitive photographic silver halide material which comprises in at least one silver halide layer or a layer adjacent thereto a compound of formula I or a compound as claimed in claim 2 and developing the exposed silver halide with a paraphenylene diamine colour developing agent thereby to liberate imagewise the group R3~S@.
9. A process according to claim 8 wherein in the compound of formula I R3 is a phenyl substituted tetrazole group.
10. A process according to claim 8 wherein the group -S-R3 is a member of the mercapto pyrimidine series, a member of the mercapto thiadiazole series, a member of the mercapto triazine series, a member of the mercapto triazole series or a member of the mercapto tetrazole series or an optionally substituted mercapto benzene.
11. A process according to any one of claims 8 to 10 wherein R2 in formula I represents the atoms necessary to complete an optionally substituted triazole, tetrazole, pyrazole or imidazole ring system.
12. A process according to any one of claims 8 to 11 wherein R1 is a group of the formula:~
where R4 is a ballasting alkyl group or comprises a ballasting alkyl group.
13. A process according to any one of claims 8 to 11 wherein R, is a group of the formula:~
where L is an-SO2-or-CO-link and R4 is as defined in claim 12.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7831402A GB2032914B (en) | 1977-08-12 | 1978-07-27 | Hetero-cyclyl-substituted phenacyl thioether derivatives for use as photographic development inhibitors |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3388377 | 1977-08-12 | ||
| GB7831402A GB2032914B (en) | 1977-08-12 | 1978-07-27 | Hetero-cyclyl-substituted phenacyl thioether derivatives for use as photographic development inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2032914A true GB2032914A (en) | 1980-05-14 |
| GB2032914B GB2032914B (en) | 1982-07-14 |
Family
ID=26262066
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7831402A Expired GB2032914B (en) | 1977-08-12 | 1978-07-27 | Hetero-cyclyl-substituted phenacyl thioether derivatives for use as photographic development inhibitors |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2032914B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0346899A2 (en) * | 1988-06-16 | 1989-12-20 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| EP0377181A2 (en) * | 1989-01-04 | 1990-07-11 | Agfa-Gevaert AG | Colour-photographic material |
| EP0661591A2 (en) | 1993-12-29 | 1995-07-05 | Eastman Kodak Company | Photographic elements containing loaded ultraviolet absorbing polymer latex |
| EP0684511A1 (en) | 1994-05-20 | 1995-11-29 | Eastman Kodak Company | Low contrast film |
| EP0695968A2 (en) | 1994-08-01 | 1996-02-07 | Eastman Kodak Company | Viscosity reduction in a photographic melt |
-
1978
- 1978-07-27 GB GB7831402A patent/GB2032914B/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0346899A2 (en) * | 1988-06-16 | 1989-12-20 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| EP0346899A3 (en) * | 1988-06-16 | 1990-05-09 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| EP0377181A2 (en) * | 1989-01-04 | 1990-07-11 | Agfa-Gevaert AG | Colour-photographic material |
| EP0377181A3 (en) * | 1989-01-04 | 1991-06-12 | Agfa-Gevaert AG | Colour-photographic material |
| EP0661591A2 (en) | 1993-12-29 | 1995-07-05 | Eastman Kodak Company | Photographic elements containing loaded ultraviolet absorbing polymer latex |
| EP0684511A1 (en) | 1994-05-20 | 1995-11-29 | Eastman Kodak Company | Low contrast film |
| EP0695968A2 (en) | 1994-08-01 | 1996-02-07 | Eastman Kodak Company | Viscosity reduction in a photographic melt |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2032914B (en) | 1982-07-14 |
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|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |