US3178286A - Light sensitive photographic color element - Google Patents
Light sensitive photographic color element Download PDFInfo
- Publication number
- US3178286A US3178286A US67484A US6748460A US3178286A US 3178286 A US3178286 A US 3178286A US 67484 A US67484 A US 67484A US 6748460 A US6748460 A US 6748460A US 3178286 A US3178286 A US 3178286A
- Authority
- US
- United States
- Prior art keywords
- color
- group
- compound
- compounds
- layer
- 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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- 239000010410 layer Substances 0.000 description 33
- 150000001875 compounds Chemical class 0.000 description 30
- 230000003647 oxidation Effects 0.000 description 16
- 238000007254 oxidation reaction Methods 0.000 description 16
- -1 Silver halide Chemical class 0.000 description 14
- 239000000463 material Substances 0.000 description 12
- 229910052709 silver Inorganic materials 0.000 description 12
- 239000004332 silver Substances 0.000 description 12
- 239000000839 emulsion Substances 0.000 description 11
- 239000011229 interlayer Substances 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 108010010803 Gelatin Proteins 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 239000000084 colloidal system Substances 0.000 description 5
- 229920000159 gelatin Polymers 0.000 description 5
- 239000008273 gelatin Substances 0.000 description 5
- 235000019322 gelatine Nutrition 0.000 description 5
- 235000011852 gelatine desserts Nutrition 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000001617 migratory effect Effects 0.000 description 3
- 101150009274 nhr-1 gene Proteins 0.000 description 3
- 125000004963 sulfonylalkyl group Chemical group 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 150000000996 L-ascorbic acids Chemical class 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 150000001923 cyclic compounds Chemical class 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002429 hydrazines Chemical class 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AYLDJQABCMPYEN-UHFFFAOYSA-N (4-azaniumylphenyl)-diethylazanium;sulfate Chemical compound OS(O)(=O)=O.CCN(CC)C1=CC=C(N)C=C1 AYLDJQABCMPYEN-UHFFFAOYSA-N 0.000 description 1
- CLYCWGGNWNTDKX-UHFFFAOYSA-N 1-chlorosulfonyloxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOS(Cl)(=O)=O CLYCWGGNWNTDKX-UHFFFAOYSA-N 0.000 description 1
- UEUIKXVPXLWUDU-UHFFFAOYSA-O 4-sulfobenzenediazonium Chemical compound OS(=O)(=O)C1=CC=C([N+]#N)C=C1 UEUIKXVPXLWUDU-UHFFFAOYSA-O 0.000 description 1
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000007730 finishing process Methods 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 229960004279 formaldehyde Drugs 0.000 description 1
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- ADPUQRRLAAPXGT-UHFFFAOYSA-M sodium;2-formylbenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1C=O ADPUQRRLAAPXGT-UHFFFAOYSA-M 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
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 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
- G03C7/392—Additives
- G03C7/39208—Organic compounds
- G03C7/39212—Carbocyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/46—Phosphinous acids [R2POH], [R2P(= O)H]: Thiophosphinous acids including[R2PSH]; [R2P(=S)H]; Aminophosphines [R2PNH2]; Derivatives thereof
Definitions
- a diagrammatic representation of an element according to the present invention is as follows:
- Silver halide layer sensitive to another color Film base When preparing photographic color images by color development of exposed silver halide layers, a silver salt image and a color image are formed, the latter being formed by the reaction of the oxidation products of the color developing substances such as the usual pdialkyl phenylene diamines with a color coupler present in said silver halide layer to form a dye.
- the reduction power of the ascorbic acid derivatives and of the hydrazine compounds is insufiicient so that the color reproduction is not satisfactorily improved when such compounds are used. It is also known that ascorbic acid and their derivatives decompose very rapidly and that their practical utility is but very limited.
- color photographic images with an improved color reproduction can be produced.
- these finished color images soon discolor which is probably due to the decomposition of the first formed leuco-derivative in the colored products. This discoloring is particularly Well noticeable at increased temperatures such as, e.g., on high-glossing the finished images.
- R represents a member selected from the group consisting of alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an aralkyl group, a substituted aralkyl group, a sulfonyl alkyl-group, a substituted sulfonyl alkyl group, a sulfonyl aryl group, a substituted sulfonyl aryl group, a sulfonyl aralkyl group and a substituted sulfonyl aralkyl group;
- A represents a member selected from the group consisting of a hydrogen atom, a halogen atom, a hydroxy group, an amino group, an alkyl group, an alkoxy group, an alkylamino group, a carboxyl group, a carboxylic acid alkali metal group, a sulfonic acid group and a sulfonic acid alkali metal group;
- X represents a member selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group, a carboxyl group, a carboxylic acid alkali metal group, a sulfonic acid group and a sulfonic acid alkali metal group;
- R and R each represent a member selected from the group consisting of a hydrogen atom, a methyl group and an ethyl group;
- R represents a member selected from the group consisting of a carboxylic acid alkali metal salt group, a sulfonic acid alkali metal salt group and a hypo phosphorous acid alkali metal salt group; and at least one of the nitrogen atoms bearing a non-migratory making group.
- This compound can be prepared by treating compound 2 with form-aldehyde and sodium bisulfite.
- This compound can be prepared by the reduction of' 4-(p-sulfo-phenylazo) -3-cetyl sulfonyl amino-N,N-diethyl: aniline and converting the latter into the hydrochloride.
- the azo dye is prepared by coupling the diazonium salt of sulfanilic acid with 3-cetyl sulfonyl amino-N,N-- diethyl aniline which has been prepared by the reaction of cetyl sulfochloride with N,N-diethyl-mcta-phenylene diamine.
- the concentration is chosen in such a way that the active compound concentration is defined between 0.025 g. to 2 g./sq. m. of interlayer but this concentration is not critical and its limits can be broadened if necessary.
- emulsifying agents are, i.a., alkyl benzene sulfonic acids having surfaceactive properties.
- a yellow filter layer between the bluesensitive layer and the green-sensitive layer in order to eliminate the sensitivity to blue of the emulsion layers sensitive resp. to green and to red.
- a yellow filter layer is usually composed of colloidal silver.
- the compounds according to the present invention can advantageously be used in the yellow filter layer since the colloidal silver exercises an oxidizing effect on the usual color developers whereby these oxidation products can diffuse to an adjacent emulsion layer to produce an undesirable color. If the compounds according to the present invention are used, these oxidation products are immediately reduced again whereby their noxious action is excluded.
- Example 1 A color photographic material, composed of an appropriate support, a silver halide layer sensitized for red and containing a color coupler for cyan, an interlayer cast from the following composition:
- the further finishing process is executed in the commonly known baths.
- This improved color reproduction can be measured, e.g., in the following way.
- the H- and D-curves of a green selection of a thin-layer material to be examined are measured behind a green and a red filter in an Ansco densitometer. Then that step of the curves is selected the density of which behind the red filter is situated the nearest possible to 0.50; the unknown density is then measured behind a green filter on the same step.
- Example 2 The same color photographic material according to Example 1, is used and also the same processing is followed, but instead of 2 g. of the Compound 1, now 1.5 g. of the Compound 2 is added to the gelatin interlayers.
- the obtained improved color reproduction is character- 6 ized by a much more improved and measured side-a sorption of 25%, in respect of a side-absorption of 37% of a similar material without addition of said compound to the interlayers.
- Example 3 The same photographic color material according to Example 1 is used and also the same processing is followed but instead of 2 g. of the Compound 1, now 2 g. of the Compound 6 are added to the gelatin interlayers and to the yellow filter layer.
- the obtained improved color reproduction is characterized by a much more improved side-absorption of 25% which has been measured, in respect of a side-absorption of 37 of a similar material without addition of said compound to the interlayers.
- a color photographic multilayer film comprising a plurality of superposed diiferentially light-sensitive silver halide emulsion layers, each of said light-sensitive layers containing a color coupler for a primary subtractive color, and a colloid layer between at least two of said silver halide emulsion layers, said colloid layer being free of light-sensitive emulsion and containing an orthodiami-ne compound selected from the group consisting of compounds having the following general formulae:
- R represents a member selected from the group consisting of an alkyl group, a hydroxy-substituted alkyl group and a sulfonyl alkyl group;
- A represents a member selected from the group consisting of a hydrogen atom, an alkyl group, an amino group and an alkyl amino group;
- X represents a member selected from the group consisting of a hydrogen atom and a carboxylic acid alkali metal group
- R and R each represent a member selected from the group consisting of a hydrogen atom and a methyl p;
- R represents a member selected from the group consisting of a sulfonic acid alkali metal salt group and a hypophosphorous acid alkali metal salt group
- the alkyl group on at least one of the nitrogen atoms being a higher alkyl group which renders said orthodiamine non-migratory.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE2039338 | 1959-11-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3178286A true US3178286A (en) | 1965-04-13 |
Family
ID=3864710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US67484A Expired - Lifetime US3178286A (en) | 1959-11-05 | 1960-11-07 | Light sensitive photographic color element |
Country Status (4)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3424583A (en) * | 1963-08-14 | 1969-01-28 | Du Pont | Photographic color reversal films |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB558258A (en) * | 1942-05-18 | 1943-12-29 | Eastman Kodak Co | Improvements in colour photographic materials |
| US2522802A (en) * | 1948-12-22 | 1950-09-19 | Gen Aniline & Film Corp | Production of yellow dye images by color development |
| US2575027A (en) * | 1949-10-29 | 1951-11-13 | Gen Aniline & Film Corp | N-substituted 4, 6-diamino metanilic acids |
| US2733143A (en) * | 1949-07-16 | 1956-01-31 | Multilayer color film for integral | |
| US3028237A (en) * | 1957-04-26 | 1962-04-03 | Agfa Ag | Masking of cyan images in color photography |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE543282A (US20030227983A1-20031211-M00013.png) * | 1955-10-20 |
-
0
- BE BE584330D patent/BE584330A/xx unknown
-
1960
- 1960-02-03 DE DEG28952A patent/DE1113138B/de active Pending
- 1960-11-07 US US67484A patent/US3178286A/en not_active Expired - Lifetime
- 1960-11-07 GB GB38150/60A patent/GB967179A/en not_active Expired
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB558258A (en) * | 1942-05-18 | 1943-12-29 | Eastman Kodak Co | Improvements in colour photographic materials |
| US2522802A (en) * | 1948-12-22 | 1950-09-19 | Gen Aniline & Film Corp | Production of yellow dye images by color development |
| US2733143A (en) * | 1949-07-16 | 1956-01-31 | Multilayer color film for integral | |
| US2575027A (en) * | 1949-10-29 | 1951-11-13 | Gen Aniline & Film Corp | N-substituted 4, 6-diamino metanilic acids |
| US3028237A (en) * | 1957-04-26 | 1962-04-03 | Agfa Ag | Masking of cyan images in color photography |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3424583A (en) * | 1963-08-14 | 1969-01-28 | Du Pont | Photographic color reversal films |
Also Published As
| Publication number | Publication date |
|---|---|
| GB967179A (en) | 1964-08-19 |
| DE1113138B (de) | 1961-08-24 |
| BE584330A (US20030227983A1-20031211-M00013.png) |
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