US2369929A - Acylamino phenol couplers - Google Patents
Acylamino phenol couplers Download PDFInfo
- Publication number
- US2369929A US2369929A US479610A US47961043A US2369929A US 2369929 A US2369929 A US 2369929A US 479610 A US479610 A US 479610A US 47961043 A US47961043 A US 47961043A US 2369929 A US2369929 A US 2369929A
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- United States
- Prior art keywords
- coupler
- compounds
- color
- general formula
- phenol
- 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.)
- Expired - Lifetime
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- -1 Acylamino phenol Chemical compound 0.000 title description 19
- 150000001875 compounds Chemical class 0.000 description 20
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 14
- 239000000975 dye Substances 0.000 description 11
- 239000010410 layer Substances 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- 229910052709 silver Inorganic materials 0.000 description 9
- 239000004332 silver Substances 0.000 description 9
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000005325 aryloxy aryl group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- RWHXMBDIUHFFST-UHFFFAOYSA-N (3-aminophenyl)-(5-chloro-2-hydroxy-4-methylphenyl)methanone Chemical compound NC=1C=C(C(=O)C2=C(C=C(C(=C2)Cl)C)O)C=CC1 RWHXMBDIUHFFST-UHFFFAOYSA-N 0.000 description 1
- DIIASMSSGMRMQF-UHFFFAOYSA-N 1-(2-amino-3-hydroxyphenyl)ethanone Chemical class CC(=O)C1=CC=CC(O)=C1N DIIASMSSGMRMQF-UHFFFAOYSA-N 0.000 description 1
- XMTQHQNLBMWCCB-UHFFFAOYSA-N 1-N,4-N-dimethylbenzene-1,4-diamine sulfuric acid Chemical compound S(=O)(=O)(O)O.CNC1=CC=C(C=C1)NC XMTQHQNLBMWCCB-UHFFFAOYSA-N 0.000 description 1
- HRBLHUVHOWWBEN-UHFFFAOYSA-N 1-n,4-n-diethylbenzene-1,4-diamine;hydrochloride Chemical compound Cl.CCNC1=CC=C(NCC)C=C1 HRBLHUVHOWWBEN-UHFFFAOYSA-N 0.000 description 1
- ADVGKWPZRIDURE-UHFFFAOYSA-N 2'-Hydroxyacetanilide Chemical class CC(=O)NC1=CC=CC=C1O ADVGKWPZRIDURE-UHFFFAOYSA-N 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
- XBTWVJKPQPQTDW-UHFFFAOYSA-N 4-n,4-n-diethyl-2-methylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C(C)=C1 XBTWVJKPQPQTDW-UHFFFAOYSA-N 0.000 description 1
- IJJSFSXLZYFTKV-UHFFFAOYSA-N 4-n-methylbenzene-1,4-diamine;hydrochloride Chemical compound Cl.CNC1=CC=C(N)C=C1 IJJSFSXLZYFTKV-UHFFFAOYSA-N 0.000 description 1
- 241000974482 Aricia saepiolus Species 0.000 description 1
- 101100423891 Caenorhabditis elegans qars-1 gene Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000244317 Tillandsia usneoides Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical group 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HTVPAACTHAQQAS-UHFFFAOYSA-N n-(2-hydroxy-4-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(C)C=C1O HTVPAACTHAQQAS-UHFFFAOYSA-N 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
- 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
- G03C7/346—Phenolic couplers
Definitions
- an object of the present invention to provide novel coupler compounds for color photography.
- a further object is to provide phenolic coupler compounds having the proper spectral absorption characteristics for use in multicolor photography.
- a still further object is to provide coupler compounds which form photoraphic images having satisfactory heat and light stability characteristics.
- coupler compounds have substituents in the 2- and -positlons with respect to the phenolic hydroxyl group, one of the substituents being an alkyl group, and the other substituent being an acylamino group.
- tuted or unsubstituted 5 Z hydrogen .or a replaceable substituent, such as chlorine, or an irreplaceable substituent, such as methyl, in a position other than para to the hydroxyl.
- the coupler compounds 01E our invention may be incorporated in the photographic layer prior to exposure, and the colored images formed by development in a. primary aromatic amino developing solution.
- the coupler molecule may be suitably enlarged, as in compounds 3 to 10, 11, 15 and 16, to render it nondifiusing in the gelatin.
- Suitable compounds are diethyl-p-phenylenediamine hydrochloride, monomethyl-p-phenylenediamine hydrochloride, and dimethyl-p-phenylenediamine sulfate.
- the paminophenols' and their substitution products may also be used where the amino group is unsubstituted. All of these developing agents have an unsubstituted amino group at which the oxidation products of the developer couple with the color forming compounds to form dye images.
- the coupling compounds used according to our invention produce dyes which are greenish-blue in color and hence are suitable for use in three color subtractive processes of color photography. These compounds have been found to yield dyes which are more stable to heat and light than those produced from the corresponding phenols in which the 5-position relative to the hydroxyl group carries no substituent.
- the coupler used according to our invention may also have other substituents such as ples 2 and 4 to 16 have not been found to confer increased stability upon the resulting dyes but may be used for purposes of making the preparation of the coupler easier or of altering the color of the dyes or changing the solubility and difiusion characteristics or the original couplers.
- the chlorine atom in the 4-position of couplers 4, 5, and 7 to 16 is lost during coupling and does not affect the characteristics of the resulting dye.
- Our development process may be employed for the production of colored photographic images in layers of gelatin or other carrier such as collodion, organic esters of cellulose, or synthetic resins.
- the carrier may be supported by a transparent medium such as glass, cellulose ester, or a non-transparent reflecting medium such as paper or an opaque cellulose ester.
- the emulsion may be coatedras a single layer or as multiple layers on the support or in the case of a transparent support as superposed layers on both sides of the support.
- the superposed layers may be difierentially sensitized and the dyes formed therein by coupling may be bleached by an oxidizing agent such as chromic acid to colorless soluble compounds.
- an oxidizing agent such as chromic acid to colorless soluble compounds.
- A- color-forming photographic developer comprising a primary aromatic amino developing agent and a phenol coupler having the general formula:
- X is an alkyl radical and R an alkyl radical.
- a color-forming photographic developer comprising a primary aromatic amino developing agent and a phenol coupler havingthe general formula:
- a photographic emulsion for forming colored images comprising a water-permeable carrier containing. a sensitive silver halide and a phenol coupler having the general formula:
- the method of producing a colored photographic image in a gelatino silver halide emulsion v layer which comprises exposing and developing agent in the presence of a phenol coupler having it with a primary aromatic amino developing agent in the presence of a phenol coupler havin the general formula:
- coupler having where X is an alkyl radical and R is an aryloxy aryl radical.
- a photographic emulsion for forming colored images comprising a water-permeable carrier containing a sensitive silver halide and a v phenol coupler having the general formula:
- Nnco--R where X is an alkyl radical and R is an alkyl radical.
- a photographic emulsion for forming colcred images comprisin a water-permeable carrier containing a sensitive silver halide and a phenol coupler having the general formula:
- a photographic emulsion for forming colored images comprising a water-permeable carrier containing a sensitive silver halide and a phenol coupler having the general formula:
- X is an alkyl radical and R is an aryloxy aryl radical.
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Description
' Patented Feb. 2o, 1945 UNITED STATES- A I PATENT OFFICE Paul W. Vittum, Rochester, N. Y., and Willard D. Peterson, Easton, Pa., assignors to Eastman Kodak Company, Rochester, N.'Y., a corporation of New Jersey No Drawing. Application Mme 18, 1943,
Serial No. 479,610 v 13 Claims. (01.95-6) This. invention relates to photographic color forming or coupling compounds and particularly to substituted phenolic'coupler compounds.
This application is a continuation-in-part of our application Serial No. 422,699, filed December 12, 1941, now U. S. Patent 2,338,676, granted J anuary 4, 1944. v a
The formation or colored photographic images byiusing a primary aromatic amino developing agent which couples with a color forming compound on development has been the subject of numerous prior patents. Most of these patents have been directed to coupler compounds which produce on development dyes which meet the requirements of subtractive color photography, that is, dyes which are colored yellow, magenta orblue-green Phenolic coupler compounds have been described in prior patents such as Fischer U. 8. Patent 1,055,155, March 4, 1913, Mannes 8: Godowsky U. S. Patent 2,039,730, May 5, 1936,'and French Patent 836,144.; French Patent 836,144
discloses acetyl-oand m-amino-phenol as cou-' piers. These acetyl aminophenols have no substituent para to the acetylamino group, and, therefore, produce dyes which are less. stable to heat and light than those produced from acetylamino phenols having a substituent para to the acetylamino group. K
It is, therefore, an object of the present invention to provide novel coupler compounds for color photography. A further object is to provide phenolic coupler compounds having the proper spectral absorption characteristics for use in multicolor photography. A still further object is to provide coupler compounds which form photoraphic images having satisfactory heat and light stability characteristics. Other objects will appear from the following description of our invention.
These objects are accomplished by the 'use of primary aromatic amino developing agents in conjunction with certain 2,5-disubstituted phenols as coupler compounds. These coupler compounds have substituents in the 2- and -positlons with respect to the phenolic hydroxyl group, one of the substituents being an alkyl group, and the other substituent being an acylamino group. These compound having the general formula:
where X=--a1kyl R=alkyl or aryl, both of which may be substi-.
tuted or unsubstituted 5 Z=hydrogen .or a replaceable substituent, such as chlorine, or an irreplaceable substituent, such as methyl, in a position other than para to the hydroxyl.
16' The following compounds illustrate couplers suitable for use according to our invention:
2-benzoylamino-8,r dimethylphencl 2-a(p-tert. amylphenoxy)-n-butyryl-amino-fi-methyl-pl enol 4 NH-co-trp-oOciHu e -t 1:. am 1 heno )-n-butyryl-amino-4-cl1loro-5- .46 (1 9 YD me ylwhenol on un s Q CH cm Golan 2-(4"-tert.amyl-3-phenoxybenzcylamino)-3,5-dimethyl-l-phenol 1 on I NlI-C o-cm-O Z-phenylacetylaminM-chloro-dmethylphenol NH-C 0Q 0 v Z-benzoylamino-4-chloro-b-methylphenol I v c 0-CH1NH Z-anilinoacetylaminoi-chloro-fi-methylphenol 2-i4'-[-(4"-tert.amylphenoxy)-n-butyrylamino1-benzoylaminoM- chloro-B-methylpenol NH-O GONE-C 0C; r 1
- chloro--Inethylp encl 2p-nitr0benzoylamlno-chloro-imethylphenol 2-m-aminobenzoyl-4-chloro-5-methylphenol NH-COCHz' 1 z-ecetamino-l-chloro-smethylphenol NH-C O- clHfl 15 l 2(4'-sec, amylbenzamino)-4-chloro-5-methylphenol NHC 0-0-0 05H A. 2-amino-5-diethylamino toluene HCl grams 2 Sodium snlfite do 5 Sodium carbonate do 30 Water to ers 1 B. 2-acetylamino-5-methylphenoL grams 2 Sodium hydroxide (10% solution) cc 10 In use, B is added to A.
In addition to their use in the developing solution, the coupler compounds 01E our invention may be incorporated in the photographic layer prior to exposure, and the colored images formed by development in a. primary aromatic amino developing solution. In the case of a multi-layer film in which color-forming compounds are incorporated in the emulsion layers, the coupler molecule may be suitably enlarged, as in compounds 3 to 10, 11, 15 and 16, to render it nondifiusing in the gelatin.
Our couplers may be incorporated in emulsions in the manner described in Mannes 8: Godowsky U. S. Patent 2,304,940, granted December 15, 1942, or Jelley 8: Vittum U. S. Patent 2,322,027 granted June 15, 1943. a
' amines themselves. Suitable compounds are diethyl-p-phenylenediamine hydrochloride, monomethyl-p-phenylenediamine hydrochloride, and dimethyl-p-phenylenediamine sulfate. The paminophenols' and their substitution products may also be used where the amino group is unsubstituted. All of these developing agents have an unsubstituted amino group at which the oxidation products of the developer couple with the color forming compounds to form dye images. v
As stated above, the coupling compounds used according to our invention produce dyes which are greenish-blue in color and hence are suitable for use in three color subtractive processes of color photography. These compounds have been found to yield dyes which are more stable to heat and light than those produced from the corresponding phenols in which the 5-position relative to the hydroxyl group carries no substituent.
In addition to the substituents in the 2- and 5-positions with respect to the phenolic hydroxyl roup, the coupler used according to our invention may also have other substituents such as ples 2 and 4 to 16 have not been found to confer increased stability upon the resulting dyes but may be used for purposes of making the preparation of the coupler easier or of altering the color of the dyes or changing the solubility and difiusion characteristics or the original couplers. The chlorine atom in the 4-position of couplers 4, 5, and 7 to 16 is lost during coupling and does not affect the characteristics of the resulting dye.
Our development process may be employed for the production of colored photographic images in layers of gelatin or other carrier such as collodion, organic esters of cellulose, or synthetic resins. The carrier may be supported by a transparent medium such as glass, cellulose ester, or a non-transparent reflecting medium such as paper or an opaque cellulose ester. The emulsion may be coatedras a single layer or as multiple layers on the support or in the case of a transparent support as superposed layers on both sides of the support. The superposed layers may be difierentially sensitized and the dyes formed therein by coupling may be bleached by an oxidizing agent such as chromic acid to colorless soluble compounds. The destruction of the dye where X is an alkyl radical and R is an aryl radical.
4. The method of producing a colored photographic image in a gelatino-silver halide emulsion layer,- which comprises exposing and developing it with a primary aromatic amino developing agent in the presence 01' a phenol coupler having 7 the general formula:
in this way does not destroy the silver image and the silver may be resensitized to develop a color a number of times thus permitting the formation of natural color images in superposed layers as described, for example, in Mannes 8: Godowsky U. S. Patent 2,113,329. Colored images may also be formed in the manner described in Mannes,
Godowsky and Wilder U. S. Patent 2,252,718.
The examples and compounds set forth in the present specification are illustrative only and it is to be understood that our invention is to be taken as limited only by the scope of the appended claims.
We claim:
1. A- color-forming photographic developer comprising a primary aromatic amino developing agent and a phenol coupler having the general formula:
NH-C O-R NH-C 0-1:
where X is an alkyl radical and R an alkyl radical.
3. A color-forming photographic developer comprising a primary aromatic amino developing agent and a phenol coupler havingthe general formula:
i on
nn -o 0-12 H -c 0-R where X is an alkyl radical and R is selected from the class consisting of alkyl and aryl roups. 5. A photographic emulsion for forming colored images comprising a water-permeable carrier containing. a sensitive silver halide and a phenol coupler having the general formula:
'7. The method of producing a colored photographic image in a gelatino silver halide emulsion v layer which comprises exposing and developing agent in the presence of a phenol coupler having it with a primary aromatic amino developing agent in the presence of a phenol coupler havin the general formula:
v OH
graphic image in a gelatino silver halide emulsion layer which comprises exposing and developing it with a primary aromatic amino developing the general formula:
NH-CO-R I where X is an alkyl radical and R an aryloxy,
layer which comprises exposing and developing it with e. primaryaromatic amino developing agent in the presence of a phenol the general formula:
coupler having where X is an alkyl radical and R is an aryloxy aryl radical.
10. A photographic emulsion for forming colored images comprising a water-permeable carrier containing a sensitive silver halide and a v phenol coupler having the general formula:
Nnco--R where X is an alkyl radical and R is an alkyl radical.
11. A photographic emulsion for forming colcred images comprisin a water-permeable carrier containing a sensitive silver halide and a phenol coupler having the general formula:
NH-CO-R where X is an alkyl radical and R is an aryloxy allnvl radical.
13. A photographic emulsion for forming colored images comprising a water-permeable carrier containing a sensitive silver halide and a phenol coupler having the general formula:
where X is an alkyl radical and R is an aryloxy aryl radical.
PAUL W. VITIUM. WILLARD D. PETERSON.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US479610A US2369929A (en) | 1943-03-18 | 1943-03-18 | Acylamino phenol couplers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US479610A US2369929A (en) | 1943-03-18 | 1943-03-18 | Acylamino phenol couplers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2369929A true US2369929A (en) | 1945-02-20 |
Family
ID=23904693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US479610A Expired - Lifetime US2369929A (en) | 1943-03-18 | 1943-03-18 | Acylamino phenol couplers |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2369929A (en) |
Cited By (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2441491A (en) * | 1944-05-12 | 1948-05-11 | Ilford Ltd | Cyanacetylamino phenol color formers for color photography |
| US2536010A (en) * | 1947-07-11 | 1950-12-26 | Gen Aniline & Film Corp | Preparation of azine dyestuff images |
| US2551570A (en) * | 1946-10-24 | 1951-05-01 | Gen Aniline & Film Corp | Azo dye components of the amino naphthol series for diazotypes |
| US2688544A (en) * | 1952-07-31 | 1954-09-07 | Eastman Kodak Co | Silver halide photographic emulsion containing dialkyl-5-(carboxyfatty acid amido) isophthalates |
| US2728660A (en) * | 1953-10-12 | 1955-12-27 | Eastman Kodak Co | Salicylic acid ester and amide photographic coupler compounds |
| US2998312A (en) * | 1955-01-28 | 1961-08-29 | Ici Ltd | New process for colour photography |
| US3506389A (en) * | 1963-08-01 | 1970-04-14 | Oreal | Hair dyeing with couplers and a 1-amino-4-substituted-alkylaminobenzene |
| US3779763A (en) * | 1972-02-03 | 1973-12-18 | Eastman Kodak Co | Phenol color couplers |
| US4334011A (en) * | 1979-12-05 | 1982-06-08 | Fuji Photo Film Co., Ltd. | Color photographic light sensitive materials |
| EP0112162A2 (en) | 1982-12-13 | 1984-06-27 | Konica Corporation | Light-sensitive silver halide photographic material |
| EP0124795A2 (en) | 1983-04-11 | 1984-11-14 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsion |
| EP0143570A2 (en) | 1983-11-02 | 1985-06-05 | Konica Corporation | Silver halide color photographic material |
| EP0147854A2 (en) | 1983-12-29 | 1985-07-10 | Fuji Photo Film Co., Ltd. | Silver halide photographic light-sensitive materials |
| DE3525900A1 (en) * | 1984-07-19 | 1986-01-23 | Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa | METHOD FOR DEVELOPING PHOTOGRAPHIC COLOR REVERSING MATERIALS |
| DE3527116A1 (en) * | 1984-07-31 | 1986-02-13 | Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa | COLOR PHOTOGRAPHIC, LIGHT-SENSITIVE SILVER HALOGENIDE MATERIAL |
| EP0201033A2 (en) | 1985-04-30 | 1986-11-12 | Konica Corporation | A method for processing silver halide color photographic materials |
| EP0202616A2 (en) | 1985-05-16 | 1986-11-26 | Konica Corporation | Method for color-developing a silver halide photographic light-sensitive material |
| EP0204530A2 (en) | 1985-05-31 | 1986-12-10 | Konica Corporation | Method for forming direct positive color image |
| EP0204175A1 (en) | 1985-05-09 | 1986-12-10 | Fuji Photo Film Co., Ltd. | Silver halide color photographic materials |
| EP0228914A2 (en) | 1985-12-28 | 1987-07-15 | Konica Corporation | Method of processing lightsensitive silver halide color photographic material |
| EP0253390A2 (en) | 1986-07-17 | 1988-01-20 | Fuji Photo Film Co., Ltd. | Photographic support and color photosensitive material |
| EP0266797A2 (en) | 1986-11-07 | 1988-05-11 | Fuji Photo Film Co., Ltd. | Method of processing silver halide color photographic material and photographic color developing composition |
| EP0313083A2 (en) | 1987-10-22 | 1989-04-26 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| EP0317983A2 (en) | 1987-11-27 | 1989-05-31 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| EP0320939A2 (en) | 1987-12-15 | 1989-06-21 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| EP0321190A2 (en) | 1987-12-15 | 1989-06-21 | Konica Corporation | Silver halide color photographic light-sensitive material |
| US4916051A (en) * | 1987-04-07 | 1990-04-10 | Konica Corporation | Silver halide color photographic light-sensitive material |
| US4990436A (en) * | 1990-01-23 | 1991-02-05 | Eastman Kodak Company | Cyan dye-forming couplers and photographic recording materials containing same |
| EP0435334A2 (en) | 1989-12-29 | 1991-07-03 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material containing yellow colored cyan coupler |
| EP0440195A2 (en) | 1990-01-31 | 1991-08-07 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| EP0452984A1 (en) | 1985-09-25 | 1991-10-23 | Fuji Photo Film Co., Ltd. | Process for processing silver halide color photographic material for photographing use |
| EP0452886A2 (en) | 1990-04-17 | 1991-10-23 | Fuji Photo Film Co., Ltd. | Method of processing a silver halide color photographic material |
| EP0476327A1 (en) | 1990-08-20 | 1992-03-25 | Fuji Photo Film Co., Ltd. | Data-retainable photographic film product and process for producing color print |
| EP0510535A1 (en) * | 1991-04-20 | 1992-10-28 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| EP0562476A1 (en) | 1992-03-19 | 1993-09-29 | Fuji Photo Film Co., Ltd. | A silver halide photographic emulsion and a photographic light-sensitive material |
| EP0563708A1 (en) | 1992-03-19 | 1993-10-06 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsion and light-sensitive material using the same |
| EP0563985A1 (en) | 1992-04-03 | 1993-10-06 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| EP0570006A1 (en) | 1992-05-15 | 1993-11-18 | Fuji Photo Film Co., Ltd. | A silver halide photographic light-sensitive material |
| EP0607905A2 (en) | 1993-01-18 | 1994-07-27 | Fuji Photo Film Co., Ltd. | Silver halide photographic material |
| US5354646A (en) * | 1986-03-26 | 1994-10-11 | Konishiroku Photo Industry Co., Ltd. | Method capable of rapidly processing a silver halide color photographic light-sensitive material |
| US5376484A (en) * | 1992-09-01 | 1994-12-27 | Konica Corporation | Photographic information recording method |
| EP0654705A2 (en) | 1993-11-24 | 1995-05-24 | Fuji Photo Film Co., Ltd. | Photographic processing composition and method of photographic processing using the same |
| WO1996013755A1 (en) | 1994-10-26 | 1996-05-09 | Eastman Kodak Company | Photographic emulsions of enhanced sensitivity |
| EP0711804A2 (en) | 1994-11-14 | 1996-05-15 | Ciba-Geigy Ag | Latent light stabilizers |
| US5616453A (en) * | 1994-08-30 | 1997-04-01 | Konica Corporation | Silver halide light-sensitive color photographic material |
| EP0777153A1 (en) | 1995-11-30 | 1997-06-04 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| EP0777152A1 (en) | 1995-11-30 | 1997-06-04 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| EP0800113A2 (en) | 1996-04-05 | 1997-10-08 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
-
1943
- 1943-03-18 US US479610A patent/US2369929A/en not_active Expired - Lifetime
Cited By (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2441491A (en) * | 1944-05-12 | 1948-05-11 | Ilford Ltd | Cyanacetylamino phenol color formers for color photography |
| US2551570A (en) * | 1946-10-24 | 1951-05-01 | Gen Aniline & Film Corp | Azo dye components of the amino naphthol series for diazotypes |
| US2536010A (en) * | 1947-07-11 | 1950-12-26 | Gen Aniline & Film Corp | Preparation of azine dyestuff images |
| US2688544A (en) * | 1952-07-31 | 1954-09-07 | Eastman Kodak Co | Silver halide photographic emulsion containing dialkyl-5-(carboxyfatty acid amido) isophthalates |
| US2728660A (en) * | 1953-10-12 | 1955-12-27 | Eastman Kodak Co | Salicylic acid ester and amide photographic coupler compounds |
| US2998312A (en) * | 1955-01-28 | 1961-08-29 | Ici Ltd | New process for colour photography |
| US3506389A (en) * | 1963-08-01 | 1970-04-14 | Oreal | Hair dyeing with couplers and a 1-amino-4-substituted-alkylaminobenzene |
| US3779763A (en) * | 1972-02-03 | 1973-12-18 | Eastman Kodak Co | Phenol color couplers |
| US4334011A (en) * | 1979-12-05 | 1982-06-08 | Fuji Photo Film Co., Ltd. | Color photographic light sensitive materials |
| EP0112162A2 (en) | 1982-12-13 | 1984-06-27 | Konica Corporation | Light-sensitive silver halide photographic material |
| EP0124795A2 (en) | 1983-04-11 | 1984-11-14 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsion |
| EP0143570A2 (en) | 1983-11-02 | 1985-06-05 | Konica Corporation | Silver halide color photographic material |
| EP0147854A2 (en) | 1983-12-29 | 1985-07-10 | Fuji Photo Film Co., Ltd. | Silver halide photographic light-sensitive materials |
| DE3525900A1 (en) * | 1984-07-19 | 1986-01-23 | Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa | METHOD FOR DEVELOPING PHOTOGRAPHIC COLOR REVERSING MATERIALS |
| DE3525900B4 (en) * | 1984-07-19 | 2005-12-29 | Fuji Photo Film Co., Ltd., Minami-Ashigara | A method of processing an imagewise exposed color reversal silver halide photographic material |
| DE3527116A1 (en) * | 1984-07-31 | 1986-02-13 | Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa | COLOR PHOTOGRAPHIC, LIGHT-SENSITIVE SILVER HALOGENIDE MATERIAL |
| US4686177A (en) * | 1984-07-31 | 1987-08-11 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive materials |
| DE3527116C2 (en) * | 1984-07-31 | 1998-05-07 | Fuji Photo Film Co Ltd | Silver halide color photographic material |
| EP0201033A2 (en) | 1985-04-30 | 1986-11-12 | Konica Corporation | A method for processing silver halide color photographic materials |
| EP0204175A1 (en) | 1985-05-09 | 1986-12-10 | Fuji Photo Film Co., Ltd. | Silver halide color photographic materials |
| EP0202616A2 (en) | 1985-05-16 | 1986-11-26 | Konica Corporation | Method for color-developing a silver halide photographic light-sensitive material |
| EP0204530A2 (en) | 1985-05-31 | 1986-12-10 | Konica Corporation | Method for forming direct positive color image |
| EP0452984A1 (en) | 1985-09-25 | 1991-10-23 | Fuji Photo Film Co., Ltd. | Process for processing silver halide color photographic material for photographing use |
| EP0228914A2 (en) | 1985-12-28 | 1987-07-15 | Konica Corporation | Method of processing lightsensitive silver halide color photographic material |
| US5354646A (en) * | 1986-03-26 | 1994-10-11 | Konishiroku Photo Industry Co., Ltd. | Method capable of rapidly processing a silver halide color photographic light-sensitive material |
| EP0253390A2 (en) | 1986-07-17 | 1988-01-20 | Fuji Photo Film Co., Ltd. | Photographic support and color photosensitive material |
| EP0266797A2 (en) | 1986-11-07 | 1988-05-11 | Fuji Photo Film Co., Ltd. | Method of processing silver halide color photographic material and photographic color developing composition |
| US4916051A (en) * | 1987-04-07 | 1990-04-10 | Konica Corporation | Silver halide color photographic light-sensitive material |
| EP0313083A2 (en) | 1987-10-22 | 1989-04-26 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| EP0317983A2 (en) | 1987-11-27 | 1989-05-31 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| EP0320939A2 (en) | 1987-12-15 | 1989-06-21 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| EP0321190A2 (en) | 1987-12-15 | 1989-06-21 | Konica Corporation | Silver halide color photographic light-sensitive material |
| EP0435334A2 (en) | 1989-12-29 | 1991-07-03 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material containing yellow colored cyan coupler |
| US4990436A (en) * | 1990-01-23 | 1991-02-05 | Eastman Kodak Company | Cyan dye-forming couplers and photographic recording materials containing same |
| EP0440195A2 (en) | 1990-01-31 | 1991-08-07 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| EP0452886A2 (en) | 1990-04-17 | 1991-10-23 | Fuji Photo Film Co., Ltd. | Method of processing a silver halide color photographic material |
| EP0476327A1 (en) | 1990-08-20 | 1992-03-25 | Fuji Photo Film Co., Ltd. | Data-retainable photographic film product and process for producing color print |
| US5328817A (en) * | 1991-04-20 | 1994-07-12 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| EP0510535A1 (en) * | 1991-04-20 | 1992-10-28 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| EP0563708A1 (en) | 1992-03-19 | 1993-10-06 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsion and light-sensitive material using the same |
| EP0562476A1 (en) | 1992-03-19 | 1993-09-29 | Fuji Photo Film Co., Ltd. | A silver halide photographic emulsion and a photographic light-sensitive material |
| EP0563985A1 (en) | 1992-04-03 | 1993-10-06 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| EP0570006A1 (en) | 1992-05-15 | 1993-11-18 | Fuji Photo Film Co., Ltd. | A silver halide photographic light-sensitive material |
| US5376484A (en) * | 1992-09-01 | 1994-12-27 | Konica Corporation | Photographic information recording method |
| EP0607905A2 (en) | 1993-01-18 | 1994-07-27 | Fuji Photo Film Co., Ltd. | Silver halide photographic material |
| EP0654705A2 (en) | 1993-11-24 | 1995-05-24 | Fuji Photo Film Co., Ltd. | Photographic processing composition and method of photographic processing using the same |
| US5616453A (en) * | 1994-08-30 | 1997-04-01 | Konica Corporation | Silver halide light-sensitive color photographic material |
| WO1996013755A1 (en) | 1994-10-26 | 1996-05-09 | Eastman Kodak Company | Photographic emulsions of enhanced sensitivity |
| EP0711804A2 (en) | 1994-11-14 | 1996-05-15 | Ciba-Geigy Ag | Latent light stabilizers |
| EP0777153A1 (en) | 1995-11-30 | 1997-06-04 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| EP0777152A1 (en) | 1995-11-30 | 1997-06-04 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| EP0800113A2 (en) | 1996-04-05 | 1997-10-08 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
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