US3615604A - Silver halide color photographic material containing cyan-forming color coupler - Google Patents
Silver halide color photographic material containing cyan-forming color coupler Download PDFInfo
- Publication number
- US3615604A US3615604A US800245A US3615604DA US3615604A US 3615604 A US3615604 A US 3615604A US 800245 A US800245 A US 800245A US 3615604D A US3615604D A US 3615604DA US 3615604 A US3615604 A US 3615604A
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- United States
- Prior art keywords
- color
- silver halide
- cyan
- forming
- coupler
- Prior art date
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- Expired - Lifetime
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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
- G03C7/34—Couplers containing phenols
- G03C7/344—Naphtholic couplers
Definitions
- This invention relates to a process for the production of color photographic cyan partial images by color development 3r?rariyzrarisrainikyi moms-grip to five atoms; e
- phenyl groups may themselves be further substituted;
- 5 is espedally a Short-chain alkyl g p
- a Short-chain alkyl g p In color photographic materials which are worked up to i g p to carbpn atoms, which alkyl g p r form color images by color-forming development, it is known desll'ably Substituted with f) S' p a5 P y to prepare the cyan part of the image from color couplers E P P the P f y group of ma comm" fmher which are usually derivatives of phenols or naphthols.
- 2 a A photographic material comprising a red sensitive silver H! H! halide emulsion layer has nowbeen found which contains o cyan-forming couplers of the following formula which Meltlng P011117 couplers on color-forming development yield cyan dyes of high stability and light-fastness even under tropical conditions: 2 0H O-CHa I C0-NH OH OBI NHCO-O b CONH- I 5 0-011; I -NHcooR I 6 40 on, on,
- X is hydrogen or halogen such as chlorine or bromine; R' and R are alkyl containing up to 18 carbon atoms, Melting point 160162" C.
- the color couplers according to the invention are prepared emulsions are then worked up to produce one-layered or mulin known manner.
- the preparation of coupler 2 is described in detail below.
- Other couplers according to the invention are prepared in a similar way.
- COUPLER 2 Stage 1. 103g. of 5-nitro-2-amino-l,4-dimethoxybenzene were suspended in 400 ml. of pyridine. l34 g. of dimethyl aniline were added. 216 g. of p-( 1,3, 3,-trimethylpentyl)- phenoxyethyl chloroformate were added dropwise at room temperature with stirring, the temperature rising to 60 C. Stirring was then continued for 30 minutes without further supply of heat. The reaction mixture was poured while stirring into 3 liters of ice water and acidified to Congo Red with 5N HCL. The oil solidified.
- the crystals were separated by suction filtration, washed neutral with water and stirred up with about 2 liters of methanol, again separated by suction filtra tion and washed with methanol.
- the crude product was purified by recrystallization from 3 liters of n-propanol with the addition of active charcoal.
- the yield was 152 g. of greenish yellow crystals of m.p. 147 to 149 C.
- Stage 2 152 g. of the nitro product produced in stage 1 were catalytically hydrogenated in 1.5 liters of tetrahydrofuran with Raney nickel at 50 C. and under 50 atmospheres excess pressure. The solution was filtered off from the Raney nickel and then concentrated by evaporation undervacuum (water-jet vacuum pump). The oily residue was stirredup with methanol, the oily amine then crystallized. The crystals were filtered off with suction and washed with methanol.
- Stage 3 87 g. of the amine produced in stage 2 and 52.8 g. of phenyl l-hydroxy-Z-naphthoate were melted and heated to l70-l75 C. in 'a vacuum, the phenol fo'rmed being distilled off. After heating during 45 minutes the hot melt was poured into 750 ml. of n-butanol. The precipitate was removed by suction filtration at room temperature and was washed with butanol. The crude product was recrystallized from 1.25 liters of butanol and washed with butanol and methanol. The yield was l l 1.5 g. ofcoupler 2 having a m.p. l60-l6lC.
- the dye couplers according to the invention can be incorporated in a diffusion-fast form in the light-sensitive silver halide emulsion layers. This can be done in known manner by emulsifying the color couplers in the emulsion layer. Processes of this type have been known for a long time and can be easily employed in the present case.
- the new compounds if they are hydrophobic, are emulsified in a solvent with or without an oil-forming agent in gelatin and this emulsion is dried, allowed to swell again in water and then mixed with the silver halide emulsion.
- Other processes are known in which the color coupler is dissolved in an organic solvent and is directly mixed with the silver halide emulsion and in which the solvent is then evaporated off.
- the color couplers according to the invention are also suitable for use in this process. These tilayered materials on a support.
- the new dye forming substances may be added not only to the light-sensitive silver halide emulsion itself but also to an adjacent insensitive layer. They may also be developed together with the color developer of the photographic material.
- Any color-forming developers which contain a primary amino group may be used for development. It is especially desirable to use those of the p-phenylenediamine type, e.g., N,N-diethyl-p-phenylene diamine, N-monomethyl-p-phenylene diamine, N,N-dimethyl-p-phenylene diamine, Z-amino- S-diethylaminotoluene, N-butyl-N-w-sulfobutyl-p-phenylenediamine and the like.
- the p-phenylenediamine type e.g., N,N-diethyl-p-phenylene diamine, N-monomethyl-p-phenylene diamine, N,N-dimethyl-p-phenylene diamine, Z-amino- S-diethylaminotoluene, N-butyl-N-w-sulfobutyl-p-phenylenediamine and
- Suitable binders for the layers are the known hydrophilic film-forming agents such as protein, especially gelatin, polyvinyl alcohol, polyvinyl pyrrolidone, cellulose derivatives such as carboxyalkyl cellulose, especially carboxyrnethyl cellulose, derivatives of alginic acid and their alkali metal salts or esters.
- the cyan-forming couplers according to the invention are advantageously added to red sensitized photographic emulsions.
- Such emulsions may also contain the usual chemical sensitizers.
- These layers may in addition be stabilized by known additives, especially by the azaindene derivatives described in the publication by Birr in Z.wiss. Phot. 47 (1952) pages 2-28.
- EXAMPLE 1 3 g. of the color coupler 6 are dissolved in 15 ml. of ethyl acetate at 55 to 60 C. and 3 g. of di-tert.-butyl phthalate are added. 50 ml. of 5 percent gelatin to which 8 g. of lauryl sulfate per kg. have been added as emulsifier are combined with the color coupler solution and intensively mixed for 10 minutes at 55 C. While this emulsion was still warm, 50 g. ofa
- photographic silver bromide emulsion which had been N.N-diethyl-p-phenylenediamine hydrochloride 2.75 g. Sodium sulfite 2 g. Potassium carbonate 75 g. Potassium bromide 0.5 g. Hydroxylamine hydrochloride l.2 g. Sodium hexametaphosphate 1.0 g. Water up tol,000 ml,
- EXAMPLE 2 3 g. of color coupler 4 are dissolved in 15 ml. of ethyl acetate at 55-60 C. This solution is added to 50 ml. of 5 percent gelatin to which 8 g. of lauryl sulfate per kg. as emulsifier has been added, and this mixture is emulsified for 10 minutes at 5560 C. While this emulsion is still warm, 50 g. of the photographic silver bromide emulsion described in example 1 are added. The light-sensitive mixture is diluted with 100 ml. of 7.5 percent gelatin solution and then applied in the usual manner to paper or a transparent support and is dried.
- the dye image may also be produced in the following developer after exposure.
- a silver halide emulsion which contains a cyan-forming color coupler of the following formula:
- the bs are the ring members required to complete a condensed benzene or tetrahydrobenzene ring.
Abstract
Color couplers of novel structure that form cyan images in photographic silver halide emulsions and are highly stable as well as produce more stable and more light-fast images.
Description
United States Patent Friedrich-Wilhelm Kunitz Leverkusen;
Willibald Pelz, Opladen; Erich Bockly, Leverkusen, all of Germany; Agia-Gevaert Aktiengesellschaft, Leverkusen, Germany [21] App1.No. 800,245
[72] Inventors [22] Filed Feb. 18, 1969 [45] Patented Oct. 26, 1971 [32] Priority Mar. 2, 1968 [33] Germany [54] SILVER HALIDE COLOR PHOTOGRAPHIC MATERIAL CONTAINING CYAN-FORMING COLOR COUPLER 4 Claims, No Drawings [52 U.S. Cl 96/100, 96/55 Primary Examiner-J. Travis Brown Attorney-Connolly and Hutz ABSTRACT: Color couplers of novel structure that form cyan images in photographic silver halide emulsions and are highly stable as well as produce more stable and more light-fast images.
SILVER IIALIDE COLOR PHOTOGRAPIIIC MATERIAL CONTAINING CYAN-FORMING COLOR COUPLER This invention relates to a process for the production of color photographic cyan partial images by color development 3r?rariyzrarisrainikyi moms-grip to five atoms; e
methyl, ethyl or butyl, aryl, in particular phenyl, or aralkyl, in particular benzyl or phenylethyl, in which the phenyl groups may themselves be further substituted;
and to a photographic material for carrying out the process. 5 is espedally a Short-chain alkyl g p In color photographic materials which are worked up to i g p to carbpn atoms, which alkyl g p r form color images by color-forming development, it is known desll'ably Substituted with f) S' p a5 P y to prepare the cyan part of the image from color couplers E P P the P f y group of ma comm" fmher which are usually derivatives of phenols or naphthols. smuems especlany l y comamfng "P to f P atoms Although a large number of such cyan-forming couplers are 10 haloge" Such as chlorme bmmme alkoxy mmle; (2) an known, no such cyan-forming couplers have yet been proarylgroup, -g- P "y an y 8 P -g- Y vided which ideally satisfy the many requirements which they Phenylethyl; have to meet. In fact, most color couplers have serious disadb y the ""8 members 'f complete a vantages. Inadequate'stability of the residual coupler which densed bellzene orletrahydl'obenlene ""8 has not been coupled with the color developer to form a dye 15 The followmg couplers are, p Suitable: image often causes discoloration of the whites of the images. The image dyes produced with oxidized color developer usually have unwanted side absorptions. Many dyes separate 0 0-4311 out, in the form of a relatively coarse color grain whilst in I others the coupling reaction proceeds too slowly. In general, 2 cry- H the cyan dyes obtainable by color-forming development do 1 not have sufficient fastness to light, satisfactory resistance to -NH-C00CH=-CH,-0 hydrolysis and the required stability to reducing agents.
It is the object of the present invention to provide cyan- 0-011, forming couplers which are stable even under tropical condi- 011 tions and which yield dyes which have high fastness to light and are stable under tropical conditions. 2 a A photographic material comprising a red sensitive silver H! H! halide emulsion layer has nowbeen found which contains o cyan-forming couplers of the following formula which Meltlng P011117 couplers on color-forming development yield cyan dyes of high stability and light-fastness even under tropical conditions: 2 0H O-CHa I C0-NH OH OBI NHCO-O b CONH- I 5 0-011; I -NHcooR I 6 40 on, on,
' -oHcHr-o--cn-cHr-+cm-cn, in which X is hydrogen or halogen such as chlorine or bromine; R' and R are alkyl containing up to 18 carbon atoms, Melting point 160162" C.
CO on, on, & NH--C0OCH -CHz-0JJHCHz-fiJ-CH, C 7 l I OH; 5H3
O-GH; Melting point -81 C.
4 OH O-GH;
CO-NH (i715:
NH-oo-ocH-cmoc1 I OCH; Cu zw Melting point 7880 C.
5 (|)H O-G Hs CONH OH! (in:
NH-CO0CH1CH;O-(F-CHz-(f-CH; CH3 CH3 O-GzHs Melting point 157 C.
C2H5 Melting point 154-155 C.
--0 O-NH 0 H3 NH-o o-ooH,oH,-o-o1 -02H5 Cu n Melting point 7678 O.
The color couplers according to the invention are prepared emulsions are then worked up to produce one-layered or mulin known manner. The preparation of coupler 2 is described in detail below. Other couplers according to the invention are prepared in a similar way.
COUPLER 2 Stage 1. 103g. of 5-nitro-2-amino-l,4-dimethoxybenzene were suspended in 400 ml. of pyridine. l34 g. of dimethyl aniline were added. 216 g. of p-( 1,3, 3,-trimethylpentyl)- phenoxyethyl chloroformate were added dropwise at room temperature with stirring, the temperature rising to 60 C. Stirring was then continued for 30 minutes without further supply of heat. The reaction mixture was poured while stirring into 3 liters of ice water and acidified to Congo Red with 5N HCL. The oil solidified. The crystals were separated by suction filtration, washed neutral with water and stirred up with about 2 liters of methanol, again separated by suction filtra tion and washed with methanol. The crude product was purified by recrystallization from 3 liters of n-propanol with the addition of active charcoal.
The yield was 152 g. of greenish yellow crystals of m.p. 147 to 149 C.
Stage 2. 152 g. of the nitro product produced in stage 1 were catalytically hydrogenated in 1.5 liters of tetrahydrofuran with Raney nickel at 50 C. and under 50 atmospheres excess pressure. The solution was filtered off from the Raney nickel and then concentrated by evaporation undervacuum (water-jet vacuum pump). The oily residue was stirredup with methanol, the oily amine then crystallized. The crystals were filtered off with suction and washed with methanol.
Yield: 128 g. ofm.p. 99.5 to 101 C.
Stage 3. 87 g. of the amine produced in stage 2 and 52.8 g. of phenyl l-hydroxy-Z-naphthoate were melted and heated to l70-l75 C. in 'a vacuum, the phenol fo'rmed being distilled off. After heating during 45 minutes the hot melt was poured into 750 ml. of n-butanol. The precipitate was removed by suction filtration at room temperature and was washed with butanol. The crude product was recrystallized from 1.25 liters of butanol and washed with butanol and methanol. The yield was l l 1.5 g. ofcoupler 2 having a m.p. l60-l6lC.
The dye couplers according to the invention can be incorporated in a diffusion-fast form in the light-sensitive silver halide emulsion layers. This can be done in known manner by emulsifying the color couplers in the emulsion layer. Processes of this type have been known for a long time and can be easily employed in the present case.
According to one known method, the new compounds, if they are hydrophobic, are emulsified in a solvent with or without an oil-forming agent in gelatin and this emulsion is dried, allowed to swell again in water and then mixed with the silver halide emulsion. Other processes are known in which the color coupler is dissolved in an organic solvent and is directly mixed with the silver halide emulsion and in which the solvent is then evaporated off. The color couplers according to the invention are also suitable for use in this process. These tilayered materials on a support.
The new dye forming substances may be added not only to the light-sensitive silver halide emulsion itself but also to an adjacent insensitive layer. They may also be developed together with the color developer of the photographic material.
Any color-forming developers which contain a primary amino group may be used for development. It is especially desirable to use those of the p-phenylenediamine type, e.g., N,N-diethyl-p-phenylene diamine, N-monomethyl-p-phenylene diamine, N,N-dimethyl-p-phenylene diamine, Z-amino- S-diethylaminotoluene, N-butyl-N-w-sulfobutyl-p-phenylenediamine and the like.
Suitable binders for the layers are the known hydrophilic film-forming agents such as protein, especially gelatin, polyvinyl alcohol, polyvinyl pyrrolidone, cellulose derivatives such as carboxyalkyl cellulose, especially carboxyrnethyl cellulose, derivatives of alginic acid and their alkali metal salts or esters.
The cyan-forming couplers according to the invention are advantageously added to red sensitized photographic emulsions. Such emulsions may also contain the usual chemical sensitizers. These layers may in addition be stabilized by known additives, especially by the azaindene derivatives described in the publication by Birr in Z.wiss. Phot. 47 (1952) pages 2-28.
EXAMPLE 1 3 g. of the color coupler 6 are dissolved in 15 ml. of ethyl acetate at 55 to 60 C. and 3 g. of di-tert.-butyl phthalate are added. 50 ml. of 5 percent gelatin to which 8 g. of lauryl sulfate per kg. have been added as emulsifier are combined with the color coupler solution and intensively mixed for 10 minutes at 55 C. While this emulsion was still warm, 50 g. ofa
photographic silver bromide emulsion which had been N.N-diethyl-p-phenylenediamine hydrochloride 2.75 g. Sodium sulfite 2 g. Potassium carbonate 75 g. Potassium bromide 0.5 g. Hydroxylamine hydrochloride l.2 g. Sodium hexametaphosphate 1.0 g. Water up tol,000 ml,
This material is then bleached, fixed and washed in the usual manner. A cyan dye image which has an absorption maximum at 678 mp. is obtained.
EXAMPLE 2 3 g. of color coupler 4 are dissolved in 15 ml. of ethyl acetate at 55-60 C. This solution is added to 50 ml. of 5 percent gelatin to which 8 g. of lauryl sulfate per kg. as emulsifier has been added, and this mixture is emulsified for 10 minutes at 5560 C. While this emulsion is still warm, 50 g. of the photographic silver bromide emulsion described in example 1 are added. The light-sensitive mixture is diluted with 100 ml. of 7.5 percent gelatin solution and then applied in the usual manner to paper or a transparent support and is dried.
After exposure and development in a developer described in example 1 and after the usual bleaching, fixing and washing, a cyan dye image which has its absorption maximum at 680 mp. is obtained.
The dye image may also be produced in the following developer after exposure.
Benzyl alcohol 3.8 ml. Sodium hexamelaphosphate 2 g. Sodium sulfite anhydrous 2 g. Sodium hydroxide 10% 5.5 ml. 4-Amino-N-ethyl-N-(fi-methariesulphonamidoethyl)-m-toluidine-sesquisulfate monohydrate 5g. Potassium bromide l g. Sodium carbonate monohydrate 50 g. \Vater up tol.000 mlv pH at 21 C. IO. 7S
After the usual bleaching, fixing and washing, a dye image which has the absorption maximum at 686 mp. is obtained.
We claim: l. A silver halide emulsion which contains a cyan-forming color coupler of the following formula:
OH OR CONH NHCOOR in which X is hydrogen or halogen; R' and R are alkyl containing up to five carbon atoms; R is an alkyl group containing up to six carbon atoms 5 which group is substituted by a phenoxy group; and
the bs are the ring members required to complete a condensed benzene or tetrahydrobenzene ring. 2. An emulsion according to claim 1, wherein the phenoxy group is substituted with an alkyl group containing up to 18 10 carbon atoms.
3. An emulsion according to claim 1', wherein which contains a cyan-forming coupler of the following formula:
OH 0-C.Hs l
C0NH- NH-COOCHz- (11113 CH oH,-0-@-oH-c1ir-+-cm-cm 4. An emulsion according to claim 1, which contains a cyanforming coupler of the following formula:
I OH O-CgH5 -C O-NH NHCOO O-GgHs CIH CH cm-cm-oQo-cm-ig-cm AH: CH;
Claims (3)
- 2. An emulsion according to claim 1, whErein the phenoxy group is substituted with an alkyl group containing up to 18 carbon atoms.
- 3. An emulsion according to claim 1, which contains a cyan-forming coupler of the following formula:
- 4. An emulsion according to claim 1, which contains a cyan-forming coupler of the following formula:
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1622920 | 1968-03-02 | ||
| DE1622920A DE1622920C3 (en) | 1968-03-02 | 1968-03-02 | Color photographic recording material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3615604A true US3615604A (en) | 1971-10-26 |
Family
ID=25753820
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US800245A Expired - Lifetime US3615604A (en) | 1968-03-02 | 1969-02-18 | Silver halide color photographic material containing cyan-forming color coupler |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3615604A (en) |
| BE (1) | BE729232A (en) |
| CH (1) | CH505407A (en) |
| DE (1) | DE1622920C3 (en) |
| FR (1) | FR2003112A1 (en) |
| GB (1) | GB1252349A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3767411A (en) * | 1970-10-20 | 1973-10-23 | Fuji Photo Film Co Ltd | Color photographic light-sensitive material forming novel cyan images |
| US4241172A (en) * | 1978-06-01 | 1980-12-23 | Konishiroku Photo Industry Co., Ltd. | Light-sensitive silver halide color photographic material |
-
1968
- 1968-03-02 DE DE1622920A patent/DE1622920C3/en not_active Expired
-
1969
- 1969-02-13 CH CH220269A patent/CH505407A/en not_active IP Right Cessation
- 1969-02-18 US US800245A patent/US3615604A/en not_active Expired - Lifetime
- 1969-02-26 GB GB1252349D patent/GB1252349A/en not_active Expired
- 1969-02-28 FR FR6905484A patent/FR2003112A1/fr not_active Withdrawn
- 1969-03-03 BE BE729232D patent/BE729232A/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3767411A (en) * | 1970-10-20 | 1973-10-23 | Fuji Photo Film Co Ltd | Color photographic light-sensitive material forming novel cyan images |
| US4241172A (en) * | 1978-06-01 | 1980-12-23 | Konishiroku Photo Industry Co., Ltd. | Light-sensitive silver halide color photographic material |
Also Published As
| Publication number | Publication date |
|---|---|
| CH505407A (en) | 1971-03-31 |
| DE1622920C3 (en) | 1981-06-04 |
| BE729232A (en) | 1969-09-03 |
| GB1252349A (en) | 1971-11-03 |
| DE1622920A1 (en) | 1970-12-17 |
| FR2003112A1 (en) | 1969-11-07 |
| DE1622920B2 (en) | 1980-06-12 |
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