US2507180A - Cyano acetamino color couplers - Google Patents
Cyano acetamino color couplers Download PDFInfo
- Publication number
- US2507180A US2507180A US727298A US72729847A US2507180A US 2507180 A US2507180 A US 2507180A US 727298 A US727298 A US 727298A US 72729847 A US72729847 A US 72729847A US 2507180 A US2507180 A US 2507180A
- Authority
- US
- United States
- Prior art keywords
- cyano
- amino
- acetamino
- compounds
- color
- 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 Cyano acetamino Chemical group 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 229910052709 silver Inorganic materials 0.000 description 8
- 239000004332 silver Substances 0.000 description 8
- 239000010410 layer Substances 0.000 description 7
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 2
- ONDHSLRUMVTTRL-UHFFFAOYSA-N 2-cyanoacetyl azide Chemical compound [N-]=[N+]=NC(=O)CC#N ONDHSLRUMVTTRL-UHFFFAOYSA-N 0.000 description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- 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
- PXJHVKRLFWZUNV-UHFFFAOYSA-N 1-n,4-n-dimethylbenzene-1,4-diamine;hydron;dichloride Chemical compound Cl.Cl.CNC1=CC=C(NC)C=C1 PXJHVKRLFWZUNV-UHFFFAOYSA-N 0.000 description 1
- SWFNPENEBHAHEB-UHFFFAOYSA-N 2-amino-4-chlorophenol Chemical compound NC1=CC(Cl)=CC=C1O SWFNPENEBHAHEB-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
- ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 5-aminonaphthalen-1-ol Chemical compound C1=CC=C2C(N)=CC=CC2=C1O ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- LMIZORQOLSLQRY-UHFFFAOYSA-N benzene;naphthalene Chemical class C1=CC=CC=C1.C1=CC=CC2=CC=CC=C21 LMIZORQOLSLQRY-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 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
- G03C7/36—Couplers containing compounds with active methylene groups
-
- 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
Definitions
- This invention relates to photography and particularly to compounds which form dyes by cou pling with the developing agent to produce colored images.
- colored photographic images may be formed by using a developer which pro prises a colored compound on development.
- the colored compound thus formed is deposited adja cent the silver grains of the silver image during the developing.
- a colored image may be formed by adding to certain developer solutions or by incorporating in the silver halide emulsion before or after exposure a compound which couples during development with the oxidation product of the developing agent and forms a colored compound which is likewise deposited adjacent the silver grains of the silver mary aromatic amino developing agent and a coupler as hereinafter defined and also includes a new or improved color development process which consists in developing a reducible silver salt image in a photographic element with the aid of a primary aromatic amino developer and in the presence of a coupler as hereinafter defined. It also includes photographic sensitive elements having such coupler in one or more emulsion layers.
- R is an aromatic nucleus or aromatic system and the position in the aromatic nucleus para or ortho to the hydroxyl group is unsubstituted with an irreplaceable group, that is, is unsubstituted or is substituted with a replaceable group such as chlorine.
- the compounds of our invention are prepared by treating an aminophenol or aminonaphthol with ethyl cyano acetate, or with ethyl acetate or another suitable solvent, and cyano acetyl azide.
- Other substituent groups such as chlorine, bromine, methyl, ethyl, methoxy, ethoxy, etc., may be present in the aromatic nucleus as long as the position in the aromatic nucleus para to the hy-- droxyl group is unsubstituted or is substituted with a group which is replaceable in the coupling reaction.
- Suitable amino phenols or amino naphthols which may be used in the preparation of our couplers are o-aminophenol, m-aminophenol, p-chloro o aminophenol, Z-amino 5 chlorophenol, 5-amino-l-naphthol, 4-chloro-5-aminol-naphthol and Z-amino-l-naphthol.
- the compounds 2-cyanoacetaminophenol and 5-cyano-acetamino-l-naphthol illustrate couplers which may be used according to our invention. These couplers may be produced as follows:
- 5-CYANOACETAMIINO-1-NAPHTHOL continued at 195-205 for one-half hour, alcohol being collected.
- the reaction mixture was cooled and poured into cc. of ethyl ether. A small amount of gum was removed-by filtration.
- the aromatic amino developing agents used with the coupler compounds of our invention include the mono-, diand tri-aminoaryl compounds and their derivatives formed by substitution in the amino group as well as in the ring such as alkylphenylenediamines and alkyltoluylenediamines. These compounds are usually used in the salt form, such as the hydrochloride or the sulphate, which are more stable than the amines themselves. Suitable compounds are diethyl-p-phenylenedi-amine hydrochloride, monoethyl pphenylenediaminehydrochloride, dimethyl p phenylenediaminehydrochloride and dimethyl -1pphenylenediamine, sulphate. De-
- jB is added to A -Qur development ,process may be employed for p du t on o or d pho g a h m e in ayer of gelatin or othe ca rier fo h s l halide such as collodion, organic esters of celluzl s or s th tic resins-c supp o t emulsion may be a ransparent mate ia s h as Ilass.
- cellulose ester or a znnn-rtransparent reliecting material such as paper or an rpnaque -cellulose ester.
- the iemulslon may be coated as a single layer on the support or as a superposed layer on one or both ,sidesof the support.
- the superposed layer may be differentially sensitized to some natural color photographic aimagesiin the well-known manner.
- a color-forming photographic developer comprising a primary aromatic amino developing agent and a coupler compound having the formula:
- a photographic emulsion for forming colored images comprising asilver halide emulsion having incorporated thereinaicou pler compound .havingthe formula:
- R is selected from the group consisting of aromatic nuclei of the benzene-and naphthalene series and the position in the aromatic nucleus para to the hydroxyl group contains a substituent of-the class consisting of hydrogen and a-replaceable group.
- a photographic emulsion for forming colored images comprising a silver halide emulsion having incorporated therein a coupler compound having the formula:
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Description
Patented May 9, 1950 CYANO ACETAMINO COLOR COUPLERS Ilmari F. Salminen and Arnold Weissherger, Rochester, N. Y., assignors to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey No Drawing. Application February 8, 1947, Serial No. 727,298
9 Claims.
This invention relates to photography and particularly to compounds which form dyes by cou pling with the developing agent to produce colored images.
It is" known that colored photographic images may be formed by using a developer which pro duces a colored compound on development. The colored compound thus formed is deposited adja cent the silver grains of the silver image during the developing. It is also known that a colored image may be formed by adding to certain developer solutions or by incorporating in the silver halide emulsion before or after exposure a compound which couples during development with the oxidation product of the developing agent and forms a colored compound which is likewise deposited adjacent the silver grains of the silver mary aromatic amino developing agent and a coupler as hereinafter defined and also includes a new or improved color development process which consists in developing a reducible silver salt image in a photographic element with the aid of a primary aromatic amino developer and in the presence of a coupler as hereinafter defined. It also includes photographic sensitive elements having such coupler in one or more emulsion layers.
We have found that compounds of the following structure are valuable couplers for color pho-' where R is an aromatic nucleus or aromatic system and the position in the aromatic nucleus para or ortho to the hydroxyl group is unsubstituted with an irreplaceable group, that is, is unsubstituted or is substituted with a replaceable group such as chlorine.
The compounds of our invention are prepared by treating an aminophenol or aminonaphthol with ethyl cyano acetate, or with ethyl acetate or another suitable solvent, and cyano acetyl azide. Other substituent groups such as chlorine, bromine, methyl, ethyl, methoxy, ethoxy, etc., may be present in the aromatic nucleus as long as the position in the aromatic nucleus para to the hy-- droxyl group is unsubstituted or is substituted with a group which is replaceable in the coupling reaction.
Suitable amino phenols or amino naphthols which may be used in the preparation of our couplers are o-aminophenol, m-aminophenol, p-chloro o aminophenol, Z-amino 5 chlorophenol, 5-amino-l-naphthol, 4-chloro-5-aminol-naphthol and Z-amino-l-naphthol.
The compounds 2-cyanoacetaminophenol and 5-cyano-acetamino-l-naphthol illustrate couplers which may be used according to our invention. These couplers may be produced as follows:
2-CYANOACETAMINO PHENOL Method 1 v Method 2 To a finely divided mixture of 22 g. of o-aminophenol in 200 cc. of ethyl acetate was added 11 g. of cyanoacetylazide with stirring. The temperature of the mixture rose from 2632. It was evaporated to dryness and the tan residue stirred with 200 CC.'0Lf water and filtered. The moist residue was transferred to a beaker containing a solution of cc. of concentrated hydrochloric acid in 300 cc. of water. The mixture was stirred five minutes, filtered, washed on the funnel with water, and dried. Yield: 13 g.; M. P. l98-200. The product was recrystallized in white needles from ethyl acetate; M. P. 209-201.
5-CYANOACETAMIINO-1-NAPHTHOL continued at 195-205 for one-half hour, alcohol being collected. The reaction mixture was cooled and poured into cc. of ethyl ether. A small amount of gum was removed-by filtration. The
filtrate was treated with Darcd and filtered into 150 cc. of ligroin, the product being precipitated. This solid was filtered and crystallized from methanol and petroleum ether. Yield: 2.6 g.; M. P. 214-215.
The aromatic amino developing agents used with the coupler compounds of our invention include the mono-, diand tri-aminoaryl compounds and their derivatives formed by substitution in the amino group as well as in the ring such as alkylphenylenediamines and alkyltoluylenediamines. These compounds are usually used in the salt form, such as the hydrochloride or the sulphate, which are more stable than the amines themselves. Suitable compounds are diethyl-p-phenylenedi-amine hydrochloride, monoethyl pphenylenediaminehydrochloride, dimethyl p phenylenediaminehydrochloride and dimethyl -1pphenylenediamine, sulphate. De-
veloping agents containing heterocyclic systems.
as described in U. S. Patent 2,196,739 are also suitable. The p-aminophenols and their substitution products may also be used where the amino group is unsubstituted. All of these compounds have an unsubstituted amino group which enables the oxidation products of the developer to couple with the color-forming compounds to form a dye image.
The following example illustrates a developing solution which may be used with the compounds of our invention.
A. peAmino-diethylaniliue sulfate ,grams- 2 Sodium hydroxide (2% solution) -cc 50 For us jB is added to A -Qur development ,process may be employed for p du t on o or d pho g a h m e in ayer of gelatin or othe ca rier fo h s l halide such as collodion, organic esters of celluzl s or s th tic resins-c supp o t emulsion may be a ransparent mate ia s h as Ilass. cellulose ester or a znnn-rtransparent reliecting .material such as paper or an rpnaque -cellulose ester. .The iemulslon may be coated as a single layer on the support or as a superposed layer on one or both ,sidesof the support. The superposed layer may be differentially sensitized to some natural color photographic aimagesiin the well-known manner.
'The examples and compounds .set forth in the rpresent specification are illustrative .only and ;it .is to be understood that .our :invention-is limited .only .byithescope of-the appended claims.
Weclaim:
1. YA color-forming photographic developer comprising a primary aromatic :amino developing agent and a coupler rcompound :havlng the forwhere R'is selected from the:group consisting of aromatic nuclei-of the benzene and naphthalene series and the position in the aromatic nucleus para tothe' hydroxylgroup:contains=a substituent of the class consisting of hydrogen and a replaceable group.
"2. .A color-charming- :photographic developer comprising :aprimaryaromatic amino. developing egent and a. cOuplneomriophd-having :the formula:
3. A color-forming photographic developer comprising a primary aromatic amino developing agent and a coupler compound having the formula:
NHCOCHaCN 4. The method of producing a colored photographic image in a silver halide emulsion layer which comprises exposing said layer and developing it with a primary aromatic amino developing agent in the presence of a coupler compound having the formula:
agent in the presence of a coupler compound having the formula:
NHGOCHzCN The m od of pro ci a .celo ed hotographic image ,in a. silver halide emulsion layer which comprises exposing said layer and.devel opns -w th a prima y aromati amino d velo n agent in the presence of a coupler compound having the formula:
N oocrnoN 7. A photographic emulsion for forming colored images comprising asilver halide emulsion having incorporated thereinaicou pler compound .havingthe formula:
where R is selected from the group consisting of aromatic nuclei of the benzene-and naphthalene series and the position in the aromatic nucleus para to the hydroxyl group contains a substituent of-the class consisting of hydrogen and a-replaceable group.
8. A photographic emulsion for forming colored images comprising a silver halide emulsion having incorporated therein a coupler compound having the formula:
9. :A photographic .remulsion for forming col- :oredimages comprising asilver halide emulsion 5 having incorporated therein a coupler compound REFERENCES CITED having the formula: The following references are of record in the NHOOOHlON file of this patent:
6 UNITED STATES PATENTS Number Name Date 2,108,602 Mannes Feb. 15, 1938 2,441,491 Kendall et a1 May 11, 1948 H 10 FOREIGN PATENTS ILMARI F. SALMINEN. Number Country Date ARNOLD W'EISSBERGER. 576,891 Great Britain Apr. 25, 1946
Claims (1)
1. A COLOR-FORMING PHOTOGRAPHIC DEVELOPER COMPRISING A PRIMARY AROMATIC AMINO DEVELOPING AGENT AND A COUPLER COMPOUND HAVING THE FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US727298A US2507180A (en) | 1947-02-08 | 1947-02-08 | Cyano acetamino color couplers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US727298A US2507180A (en) | 1947-02-08 | 1947-02-08 | Cyano acetamino color couplers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2507180A true US2507180A (en) | 1950-05-09 |
Family
ID=24922112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US727298A Expired - Lifetime US2507180A (en) | 1947-02-08 | 1947-02-08 | Cyano acetamino color couplers |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2507180A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2680731A (en) * | 1950-07-05 | 1954-06-08 | Du Pont | Acetals containing a cyanoacetyl group |
| US2680730A (en) * | 1950-07-05 | 1954-06-08 | Du Pont | Acetals of polyhydric alcohols |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2108602A (en) * | 1935-03-21 | 1938-02-15 | Eastman Kodak Co | Photographic color-forming compounds |
| GB576891A (en) * | 1944-05-12 | 1946-04-25 | John David Kendall | Improvements in or relating to colour photography |
-
1947
- 1947-02-08 US US727298A patent/US2507180A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2108602A (en) * | 1935-03-21 | 1938-02-15 | Eastman Kodak Co | Photographic color-forming compounds |
| GB576891A (en) * | 1944-05-12 | 1946-04-25 | John David Kendall | Improvements in or relating to colour photography |
| US2441491A (en) * | 1944-05-12 | 1948-05-11 | Ilford Ltd | Cyanacetylamino phenol color formers for color photography |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2680731A (en) * | 1950-07-05 | 1954-06-08 | Du Pont | Acetals containing a cyanoacetyl group |
| US2680730A (en) * | 1950-07-05 | 1954-06-08 | Du Pont | Acetals of polyhydric alcohols |
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