US2154918A - Coupling compounds for color forming development - Google Patents
Coupling compounds for color forming development Download PDFInfo
- Publication number
- US2154918A US2154918A US216293A US21629338A US2154918A US 2154918 A US2154918 A US 2154918A US 216293 A US216293 A US 216293A US 21629338 A US21629338 A US 21629338A US 2154918 A US2154918 A US 2154918A
- Authority
- US
- United States
- Prior art keywords
- color
- color forming
- development
- coupling compounds
- forming development
- 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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- 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
Definitions
- the present invention relates to coupling compounds for color forming development.
- Color photographic pictures have been produced with the aid of color developing dyestufl. components having active methylene groups which in the development of a latent silver image by me'ans of a developer containing a free amino-group.
- Such dyestuii components are, for example, derivatives of aceto-acetic acid esters,
- a further object of the invention resides in the provision of a new and improved class of dyestufi components, color formers or coupling compounds.
- Still another object of the invention is the proa the new class of color formers.
- a further object is to provide a photographic emulsion for color forming development having incorporated compounds from the new class of color formers being fast to diffusion with respect to the silver halide emulsions.
- R stands for alkyl, aryl and aralkyl
- X is a suitable inorganic acid radical, for example Cl
- ketones there may be used, for example, chloroacetophenone, bromacetophenone, monochloracetone,symmetrical dichloracetone, bromacetonaphthone, para-phenylbromacetophenone, para-phenylc fi p 5 none and diphenylene:para-para'-dichloromethyl ketone.
- the reaction of the methyl ketones and pyridine derivatives is exothermic.
- the opera tion of forming the compound may proceed in the presence or absence of a solvent.
- Suitable so1- m vents are, for example, benzene or ether.
- the new dyestufi components may be added to 15 the developer or to the emulsion.
- yellow dyestuff pictures are produced.
- groups are, for instance, substantive groups as described in U. S. patent application Ser. No. 72,718 filed April 4, 1936, radicals of highly polymeric carboxylic acids as describedinU. S. patent application Ser. No. 90,726 filed July 15, 1936, 30 aliphatic radicals consisting of an extended saturated or unsaturated carbon chain as described in U. S. patent application Ser.No.
- radicals of carbohydrates U. S. patent application Ser. No. 159,518 filed August 17, 1937
- radicalsof natural resins U. S. patent application Ser. No. 164,499 filed September 18, 1937
- sterol radicals U. S. patent application Ser. No. 166,832 filed Octoberl, 1937
- radical ofithe dyestuff component itself recurs periodically (U. S. 5 3 patent application Ser. No. 171,701 filed October 29, 1937).
- radicals may be introduced into the molecule of the dyestufl com-' ponents which make the latter fast to diflusion, which radicals consist of hydroaromatic and Such ' chloride of the formula hydro-heterocyclic residues, then further menthane radicals (U; S. patent application Ser. No. 176,058 filed November 23, 1937).
- These groups may be introduced either directly into the ketone, as for example into the diphenylacetyl chloride, into the pyridine nucleus or at any other position in the molecule, for example into the benzene nucleus of the bromacetophenone and indeed either directly or by means of an amino-, hydroxyl-, or carboxyl group in the form of an acid amide or an ester.
- the dyestuif components may be used in the production of both single layer materials and multi-layer materials, and in the latter case the layers may be arranged on one or both sides of a support. Alternatively a mixture of emulsion particles containing different dyestufl components may be applied to the support.
- ture may be produced by simple color forming development or by reversal development as described in U. S. patent applications Ser. No.
- the above described coupling compounds have an improved reactivity and form the desired dyestufls more easily than the hitherto known. color formers, since the reactive methylene group appears to be activated by the vicinal pyridine nucleus.
- Example 1 An exposed silver halide emulsion layer is developed with a developer of the following composition:
- Example 2 An exposed silver halide emulsion layer is developed with a developer of the .following composition:
- Ayellow dyestufl picture is obtained;
- Example 3.--3 grams of diphenylacylpyridinlum I 000g Ol are dissolved in 25 cc. of methanol end cc. of water, and the solution is added to 400 cc. of a gelatine emulsion of 5 percent strength, and the latter iscast to form a layer.
- dimethyl-aminoaniline there is obtained a yellow picture.
- a color forming developer capable of forming a dyestuff with the oxidation product of an aro-' matic amino developer, a pyridine derivative of the following general formula improvement which comprises employing as "a color forming developer a composition of matter comprising an aqueous solution of an alkali, an
- Silver halide emulsion for color photography capable of beingdeveloped in color by means of an aromatic amino develop'r, said silver halii'le emulsion containing a pyridine derivative of the following general formula inwhichRisamembei-ofthegroupconsisting of alkyL-aryl, and aralkyl, and x is an anion;
- a color-forming developer comprising an aqueoussolution of an alhli. an aromatic amino developlng agent, and a pyridine derivative of in which R is a. member of the group eonsisfln:
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Description
Patented Apr. 18,1939
ING v Wilhelm Schneider and Hans Loleit, Dessau, Germany, asaignor' to Asia Ansco Corporation, Binghamton, N. Y., a corporation of New York No Drawing. 'Applicafion June 28, 1938, Serial No. 216,293. In Germany July 30, 1937 claims. (on. 95-88) The present invention relates to coupling compounds for color forming development.
Color photographic pictures have been produced with the aid of color developing dyestufl. components having active methylene groups which in the development of a latent silver image by me'ans of a developer containing a free amino-group.
produce a colored compound in the place of the silver image. Such dyestuii components are, for example, derivatives of aceto-acetic acid esters,
or pyrazolone, of malonic acid esters, of cyanoacetophenone, of cumaranone and ofhydrowthionaphthehe. I
It is an object of the present invention to provide an improvement in th process of producing photographic color pictures by color forming development.
A further object of the invention resides in the provision of a new and improved class of dyestufi components, color formers or coupling compounds.
Still another object of the invention is the proa the new class of color formers.
A further object is to provide a photographic emulsion for color forming development having incorporated compounds from the new class of color formers being fast to diffusion with respect to the silver halide emulsions.
Further objects of the invention will appear from the detailed specification following hereinafter.
We-have found that an improvement in the process of producing photographic color picturesby color forming development may be obtained by employing as the color forming compounds capable of forming a dyestuii with the oxidation product of an amino developer a pyridine derivative of the following general formula:
in which R stands for alkyl, aryl and aralkyl; X is a suitable inorganic acid radical, for example Cl,
55 and its derivatives, for example picoline, 3-aminopyridine or dipyridine. As ketones there may be used, for example, chloroacetophenone, bromacetophenone, monochloracetone,symmetrical dichloracetone, bromacetonaphthone, para-phenylbromacetophenone, para-phenylc fi p 5 none and diphenylene:para-para'-dichloromethyl ketone. The reaction of the methyl ketones and pyridine derivatives is exothermic. The opera tion of forming the compound may proceed in the presence or absence of a solvent. Suitable so1- m vents are, for example, benzene or ether. By
- double decomposition there may be obtained from the aforesaid halogen derivatives chlorates, sulfates, or the like.
The new dyestufi components may be added to 15 the developer or to the emulsion. In the development with a para-dialkylaminoaniline, yellow dyestuff pictures are produced.
when. these dyestufi coupling components are mixed in the photographic layer they should be made ,fast to difiusion in the medium oi the layer by introduction of groups, which owing their chemical structure are capable of imparting to the dyestufi components fastncss to diffusion while retaining their solubility in water. groups are, for instance, substantive groups as described in U. S. patent application Ser. No. 72,718 filed April 4, 1936, radicals of highly polymeric carboxylic acids as describedinU. S. patent application Ser. No. 90,726 filed July 15, 1936, 30 aliphatic radicals consisting of an extended saturated or unsaturated carbon chain as described in U. S. patent application Ser.No. 94,340 filed August 5, 1936, said carbon chains preferably containing radicals which impart to the finished comthe layers or from one layer to the other, such as 40 for instance polypeptide radicals (U. S. patent application Ser. No. 158,860 filed'August 13, 1937),
radicals of carbohydrates (U. S. patent application Ser. No. 159,518 filed August 17, 1937), radicalsof natural resins (U. S. patent application Ser. No. 164,499 filed September 18, 1937), sterol radicals (U. S. patent application Ser. No. 166,832 filed Octoberl, 1937). Furthermore there may be used compounds in which the radical ofithe dyestuff component itself recurs periodically (U. S. 5 3 patent application Ser. No. 171,701 filed October 29, 1937). Furthermore radicals may be introduced into the molecule of the dyestufl com-' ponents which make the latter fast to diflusion, which radicals consist of hydroaromatic and Such ' chloride of the formula hydro-heterocyclic residues, then further menthane radicals (U; S. patent application Ser. No. 176,058 filed November 23, 1937).
These groups may be introduced either directly into the ketone, as for example into the diphenylacetyl chloride, into the pyridine nucleus or at any other position in the molecule, for example into the benzene nucleus of the bromacetophenone and indeed either directly or by means of an amino-, hydroxyl-, or carboxyl group in the form of an acid amide or an ester.
The dyestuif components may be used in the production of both single layer materials and multi-layer materials, and in the latter case the layers may be arranged on one or both sides of a support. Alternatively a mixture of emulsion particles containing different dyestufl components may be applied to the support.
In the exposed silver halide emulsion the pic.-
ture may be produced by simple color forming development or by reversal development as described in U. S. patent applications Ser. No.
148,731 filed June 17, 1937, and Ser. No. 100,319 flled September 11, 1936.
. The above described coupling compounds have an improved reactivity and form the desired dyestufls more easily than the hitherto known. color formers, since the reactive methylene group appears to be activated by the vicinal pyridine nucleus.
The following examples illustrate the invention:
Example 1.-An exposed silver halide emulsion layer is developed with a developer of the following composition:
(a) Para-dimethylaminoaniline ....grams 1 Anhydrous sodium carbonate.. do 15 Sodium sulflte do Water cc 250 Potassium bromide "grams" 1 (b) Phenacylpicolinium chloride do 1. 8
Methanol cc.. 10
when the silver has been dissolved away a yellow dyestufl picture is obtained.
Example 2.An exposed silver halide emulsion layer is developed with a developer of the .following composition:
Ayellow dyestufl picture is obtained; Example 3.--3 grams of diphenylacylpyridinlum I 000g Ol are dissolved in 25 cc. of methanol end cc. of water, and the solution is added to 400 cc. of a gelatine emulsion of 5 percent strength, and the latter iscast to form a layer. By developing the exposed layer with dimethyl-aminoaniline there is obtained a yellow picture.
What we claim is:
1. In a process of producing photographic color pictures by color forming development, the improvement which comprises employing as the .color forming compound capable of forming a dyestuff with the oxidation product of an aro-' matic amino developer, a pyridine derivative of the following general formula improvement which comprises employing as "a color forming developer a composition of matter comprising an aqueous solution of an alkali, an
aromatic amino developing agent and a pyridine derivative of the following general formula cl n-cocfil x in which R is a member of the group consisting of aikyl, aryl, and aralkyl, and X is an anion.
3. In a process of producing photographic color pictures by color forming development, the
' improvement which comprises employing as a light-sensitive element a photographic silver halide emulsion containing as the color forming compound capable of forming a dyestufl with the oxidation product of an aromatic amino developer, a pyridine derivative of the following general formula in which R is a member 01' the group consisting of alkyl, aryl, and aralkyl, and X is an anion, said pyridine derivative containing in its molecule a radical, which imparts thereto fastness to diffusion with respect to the binding agent of the emulsion,'while retainingits solubility in aqueous liquids.
4. Silver halide emulsion for color photography capable of beingdeveloped in color by means of an aromatic amino develop'r, said silver halii'le emulsion containing a pyridine derivative of the following general formula inwhichRisamembei-ofthegroupconsisting of alkyL-aryl, and aralkyl, and x is an anion;
*5. A color-forming developer comprising an aqueoussolution of an alhli. an aromatic amino developlng agent, and a pyridine derivative of in which R is a. member of the group eonsisfln:
the following general formula or alkyl, ml, and aralkyi, and x is an anion.
'wnnmm scmmmm. i we 1.0mm
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEI0058706 | 1937-07-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
US2154918A true US2154918A (en) | 1939-04-18 |
Family
ID=7194843
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US216293A Expired - Lifetime US2154918A (en) | 1937-07-30 | 1938-06-28 | Coupling compounds for color forming development |
Country Status (4)
Country | Link |
---|---|
US (1) | US2154918A (en) |
BE (1) | BE429448A (en) |
FR (1) | FR841425A (en) |
GB (1) | GB504376A (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2421693A (en) * | 1944-09-16 | 1947-06-03 | Gen Aniline & Film Corp | Imidazolone color formers |
US2433632A (en) * | 1942-12-23 | 1947-12-30 | Rca Corp | Fibrous sheet material for the electrolytic formation of azo dye image records thereon |
US2440526A (en) * | 1942-12-23 | 1948-04-27 | Nellie W Solomon | Fibrous sheet material for the electrolytic formation of an azo dyestuff thereon |
US2440954A (en) * | 1945-08-23 | 1948-05-04 | Du Pont | Process for eliminating stain from color-yielding elements by treatment with aromatic aldehydes containing an acyl group |
US2531091A (en) * | 1945-08-03 | 1950-11-21 | Gevaert Photo Prod Nv | N-acetonyl-pyridinium chloride as an azo coupling component in diazotypes |
US2776116A (en) * | 1953-10-29 | 1957-01-01 | Acme Highway Prod | Beam guard for highways and the like |
US5035987A (en) * | 1989-10-05 | 1991-07-30 | Agfa Gevaert Aktiengesellschaft | Color photographic recording material containing a DIR coupler |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2418748A (en) * | 1944-06-07 | 1947-04-08 | Gen Aniline & Film Corp | Heterocyclic color couplers |
-
0
- BE BE429448D patent/BE429448A/xx unknown
-
1937
- 1937-08-24 GB GB23190/37A patent/GB504376A/en not_active Expired
-
1938
- 1938-06-28 US US216293A patent/US2154918A/en not_active Expired - Lifetime
- 1938-07-29 FR FR841425D patent/FR841425A/en not_active Expired
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2433632A (en) * | 1942-12-23 | 1947-12-30 | Rca Corp | Fibrous sheet material for the electrolytic formation of azo dye image records thereon |
US2440526A (en) * | 1942-12-23 | 1948-04-27 | Nellie W Solomon | Fibrous sheet material for the electrolytic formation of an azo dyestuff thereon |
US2421693A (en) * | 1944-09-16 | 1947-06-03 | Gen Aniline & Film Corp | Imidazolone color formers |
US2531091A (en) * | 1945-08-03 | 1950-11-21 | Gevaert Photo Prod Nv | N-acetonyl-pyridinium chloride as an azo coupling component in diazotypes |
US2440954A (en) * | 1945-08-23 | 1948-05-04 | Du Pont | Process for eliminating stain from color-yielding elements by treatment with aromatic aldehydes containing an acyl group |
US2776116A (en) * | 1953-10-29 | 1957-01-01 | Acme Highway Prod | Beam guard for highways and the like |
US5035987A (en) * | 1989-10-05 | 1991-07-30 | Agfa Gevaert Aktiengesellschaft | Color photographic recording material containing a DIR coupler |
Also Published As
Publication number | Publication date |
---|---|
FR841425A (en) | 1939-05-19 |
GB504376A (en) | 1939-04-24 |
BE429448A (en) |
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