US3408193A - Coating compositions for the coating out of anionic mordant-acid dye layers - Google Patents
Coating compositions for the coating out of anionic mordant-acid dye layers Download PDFInfo
- Publication number
- US3408193A US3408193A US418881A US41888164A US3408193A US 3408193 A US3408193 A US 3408193A US 418881 A US418881 A US 418881A US 41888164 A US41888164 A US 41888164A US 3408193 A US3408193 A US 3408193A
- Authority
- US
- United States
- Prior art keywords
- coating
- acid dye
- mordant
- layers
- compositions
- 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
Links
- 238000000576 coating method Methods 0.000 title claims description 43
- 239000011248 coating agent Substances 0.000 title claims description 41
- 239000000980 acid dye Substances 0.000 title claims description 16
- 239000008199 coating composition Substances 0.000 title description 5
- 125000000129 anionic group Chemical group 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims description 19
- 239000000084 colloidal system Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 7
- -1 silver halide Chemical class 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 108010010803 Gelatin Proteins 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 239000000983 mordant dye Substances 0.000 description 4
- 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 3
- 239000000463 material Substances 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- WICCYSZGCBTHGG-UHFFFAOYSA-N 1,3-benzoxazole pyrazol-3-one Chemical class N1=NC(C=C1)=O.O1C=NC2=C1C=CC=C2 WICCYSZGCBTHGG-UHFFFAOYSA-N 0.000 description 2
- 238000000586 desensitisation Methods 0.000 description 2
- 229920002113 octoxynol Polymers 0.000 description 2
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 2
- 229930182490 saponin Natural products 0.000 description 2
- 150000007949 saponins Chemical class 0.000 description 2
- XYYUAOIALFMRGY-UHFFFAOYSA-N 3-[2-carboxyethyl(dodecyl)amino]propanoic acid Chemical compound CCCCCCCCCCCCN(CCC(O)=O)CCC(O)=O XYYUAOIALFMRGY-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 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
- G03C1/00—Photosensitive materials
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
- G03C1/835—Macromolecular substances therefor, e.g. mordants
-
- 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
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/38—Dispersants; Agents facilitating spreading
Definitions
- This invention relates to mordant-dye layers in which certain particular coating aids are employed in their composition.
- Patent No. 3,282,699 describes mordant-dye compositions for use as layers in photographic elements such as for filter layers or antihalation layers which compositions are composed of a basic mordant having recurring basic groups, an acid dye, a water permeable hydrophilic colloid binder and as the coating aid therein saponin.
- Saponin varies widely in purity and often contains material which desensitizes or has other derogatory elfects upon the silver halide emulsion with which it comes in contact. Therefore, it is desirable in photographic uses to use synthetic coating aids which have a uniform composition and are free of materials which might exert a derogatory effect on the photographic materials which they contact.
- the common coating aids such as of the anionic type in mordant-dye compositions
- high concentrations thereof are often needed to obtain satisfactory coatings.
- these anionic coating aids tend to promote wandering of the dyes in the compositions into adjacent photographic emulsion layers resulting in desensitization of those layers.
- One object of our invention is to provide mordant-acid dye coating compositions which use a synthetic coating aid in the coating out of those compositions onto a support.
- Another object of our invention is to provide basic mordant-acid dye compositions containing coating aids which do not promote the wandering of the dyes into adjacent silver halide photographic emulsion layers or require use in high proportions as is the case with many of the coating aids commonly considered useful in coating out photographic layers.
- compositions in accordance with our invention are susceptible to coating out as layers at speeds of 50-500 feet per minute in coating operations in which hoppers of the type described in US. Patents Nos. 2,681,294 and 2,761,791 are used.
- Example 1 Parts coating aid per Repellency Coating aid parts gelatin coating by wt. defects Triton-X 200 (p-tert-octylphenoxy ethoxy ethyl sulfonate) 7 High. Triton-X 200 10. 6 Fewer. Deriphat 151 (sodium N-coco-betaaminopropionate) 2 None.
- coco represents a. mixture of high molecular weight hydrocarbon radlcals corresponding to those present in the esters in cocoanut oil.
- Example 2 Two multilayer color films were prepared and coated as described in Example 16 of US. Patent No. 2,944,900 except that a yellow filter layer of the type described in Example 1 was used instead of the Carey Lea silver-blue light filter layer and a gelatin-basic mordant-magenta acid dye layer was coated between the green sensitive and red sensitive layers.
- an anionic coating aid was used in the mordant-dye layers and in the other a sodium salt of an alkyl aminopropionate as listed in Patent No. 3,133,816 was employed.
- the films were exposed on a sensitometer and were processed as described in Example 2 of U.S. Patent No. 2,944,900. The results obtained were as follows:
- a composition adapted to the coating out of layers for photographic products comprising in an aqueous system a hydrophilic colloid, a polymeric mordant having recurring basic groups, an acid dye and a coating aid selected from the group consisting of the compounds having the following general formulae:
- a photographic element having as a layer therein a mixture of a hydrophilic colloid, a polymeric mordant having recurring basic groups, an acid dye and .a coating 3 aid selected from the group consisting of the compounds having the following general formulae:
- ANH(CH COOM AN (CH COOM]- wherein A is selected from the group of aliphatic hydrocarbon radicals and aliphatic acyl radicals of 8-20 carbon atoms, x 12 and M is a cation which will contribute to the water solubility of the coating aid.
- a composition adapted to the coating out of layers for photographic products comprising in an aqueous system a hydrophilic colloid, a polymeric mordant having recurring basic groups, an acid dye and as the coating aid therein a compound having the formula:
- RCON[ (CH COOM] 2 in which x l2 and R is a radical having 11-17 carbon atoms and M is a cation contributing to water solubility of the coating aid.
- composition adapted to the coating out of layers for photographic products comprising in an aqueous system a hydrophilic colloid, a polymeric mordant having recurring basic groups, an acid dye and as the coating aid therein a compound having the formula:
- R is an aliphatic hydrocarbon radical having from 8 to 20 carbon atoms and X is selected from the group consisting of hydrogen, an alkali metal, ammonium and an organic amine cation.
- a composition adapted to the coating out of layers for photographic products comprising in an aqueous system a hydrophilic colloid, a polymeric mordant having recurring basic groups, an acid dye and as the coating aid therein sodium N-coco-beta-aminopropionate.
- composition adapted to the coating out of layers for photographic products comprising in an aqueous system gelatin as the hydrophilic colloid, poly-alpha-methylallyl-N-guanidyl-ketimine as the mordant, yellow sulfonated benzoXazole-pyrazolone dye and as the coating aid a compound selected from the group consisting of those having the following general formulae:
- a composition adapted to the coating out of layers for photographic products comprising in an aqueous system gelatin as a hydrophilic colloid, poly-alpha-methylallyl-N-guanidylketimine as the mordant, yellow sulfonated benZoXaZole-pyrazolone as the acid dye and as the coating aid sodium N-coco-beta-aminopropionate.
Description
United States Patent 3,408,193 COATING COMPOSITIONS FOR THE COATING OUT OF ANIONIC MORDANT-ACID DYE LAYERS Wilfred L. Wolf and Clark Beckett, Rochester, N.Y., as-
signors to Eastman Kodak Company, Rochester, N.Y., a corporation of New Jersey No Drawing. Filed Dec. 16, 1964, Ser. No. 418,881 8 Claims. (Cl. 96-84) This invention relates to mordant-dye layers in which certain particular coating aids are employed in their composition.
Jones and Milton application Ser. No. 167,666, now
Patent No. 3,282,699 describes mordant-dye compositions for use as layers in photographic elements such as for filter layers or antihalation layers which compositions are composed of a basic mordant having recurring basic groups, an acid dye, a water permeable hydrophilic colloid binder and as the coating aid therein saponin. Saponin varies widely in purity and often contains material which desensitizes or has other derogatory elfects upon the silver halide emulsion with which it comes in contact. Therefore, it is desirable in photographic uses to use synthetic coating aids which have a uniform composition and are free of materials which might exert a derogatory effect on the photographic materials which they contact. In using the common coating aids such as of the anionic type in mordant-dye compositions high concentrations thereof are often needed to obtain satisfactory coatings. In addition these anionic coating aids tend to promote wandering of the dyes in the compositions into adjacent photographic emulsion layers resulting in desensitization of those layers.
The specification of application Ser. No. 167,666, filed J an. 22, 1962, describes photographic elements containing layers composed of basic mordant, acid dye and hydrophilic colloid and is incorporated herein by reference.
One object of our invention is to provide mordant-acid dye coating compositions which use a synthetic coating aid in the coating out of those compositions onto a support. Another object of our invention is to provide basic mordant-acid dye compositions containing coating aids which do not promote the wandering of the dyes into adjacent silver halide photographic emulsion layers or require use in high proportions as is the case with many of the coating aids commonly considered useful in coating out photographic layers. Other objects of our invention will appear herein,
We have found that basic mordant-acid dye coating compositions which contain as the coating aids therein salts of alkyl substituted or acyl substituted amino acids as described in U.S. Patents Nos. 3,133,816 and 3,142,568 and in US. application Ser. No. 225,108 give coatings of good uniformity. The disclosures of the patents (Nos. 3,133,816 and 3,142,568) and the application (No. 225,- 108) referred to are incorporated herein by reference. We have found that concentrations in the coating compositions of no more than of these coating aids based on the gelatin can be used with good results although greater amounts can be used if desired. We have found that coating aids of this type do not cause wandering of the dye into adjacent silver halide photographic emulsion layers, hence, desensitization of the emulsion layer is avoided. We have found that compositions in accordance with our invention are susceptible to coating out as layers at speeds of 50-500 feet per minute in coating operations in which hoppers of the type described in US. Patents Nos. 2,681,294 and 2,761,791 are used.
Patented Oct. 29, 1968 The following examples will illustrate our invention:
Example 1 Parts coating aid per Repellency Coating aid parts gelatin coating by wt. defects Triton-X 200 (p-tert-octylphenoxy ethoxy ethyl sulfonate) 7 High. Triton-X 200 10. 6 Fewer. Deriphat 151 (sodium N-coco-betaaminopropionate) 2 None.
Where coco represents a. mixture of high molecular weight hydrocarbon radlcals corresponding to those present in the esters in cocoanut oil.
Example 2 Two multilayer color films were prepared and coated as described in Example 16 of US. Patent No. 2,944,900 except that a yellow filter layer of the type described in Example 1 was used instead of the Carey Lea silver-blue light filter layer and a gelatin-basic mordant-magenta acid dye layer was coated between the green sensitive and red sensitive layers. In preparing one film an anionic coating aid was used in the mordant-dye layers and in the other a sodium salt of an alkyl aminopropionate as listed in Patent No. 3,133,816 was employed. The films were exposed on a sensitometer and were processed as described in Example 2 of U.S. Patent No. 2,944,900. The results obtained were as follows:
The invention has been described in considerable detail with particular reference to certain preferred embodiments thereof, but it will be understood that variations and modifications can be elfected within the spirit and scope of the invention as described hereinabove and as defined in the appended claims.
We claim:
1. A composition adapted to the coating out of layers for photographic products comprising in an aqueous system a hydrophilic colloid, a polymeric mordant having recurring basic groups, an acid dye and a coating aid selected from the group consisting of the compounds having the following general formulae:
ANH(CH COOM and AN[(CH ),,COOM] wherein A is selected from the group of aliphatic hydrocarbon radicals and aliphatic acyl radicals of 8-20 carbon atoms, x=1-2 and M is a cation which will contribute to the water solubility of the coating aid.
2. A photographic element having as a layer therein a mixture of a hydrophilic colloid, a polymeric mordant having recurring basic groups, an acid dye and .a coating 3 aid selected from the group consisting of the compounds having the following general formulae:
ANH(CH COOM AN (CH COOM]- wherein A is selected from the group of aliphatic hydrocarbon radicals and aliphatic acyl radicals of 8-20 carbon atoms, x=12 and M is a cation which will contribute to the water solubility of the coating aid.
3. A composition adapted to the coating out of layers for photographic products comprising in an aqueous system a hydrophilic colloid, a polymeric mordant having recurring basic groups, an acid dye and as the coating aid therein a compound having the formula:
RCON[ (CH COOM] 2 in which x=l2 and R is a radical having 11-17 carbon atoms and M is a cation contributing to water solubility of the coating aid.
4. A composition adapted to the coating out of layers for photographic products comprising in an aqueous system a hydrophilic colloid, a polymeric mordant having recurring basic groups, an acid dye and as the coating aid therein a compound having the formula:
RNHCHZCHZCOOX wherein R is an aliphatic hydrocarbon radical having from 8 to 20 carbon atoms and X is selected from the group consisting of hydrogen, an alkali metal, ammonium and an organic amine cation.
and
6. A composition adapted to the coating out of layers for photographic products comprising in an aqueous system a hydrophilic colloid, a polymeric mordant having recurring basic groups, an acid dye and as the coating aid therein sodium N-coco-beta-aminopropionate.
7. A composition adapted to the coating out of layers for photographic products comprising in an aqueous system gelatin as the hydrophilic colloid, poly-alpha-methylallyl-N-guanidyl-ketimine as the mordant, yellow sulfonated benzoXazole-pyrazolone dye and as the coating aid a compound selected from the group consisting of those having the following general formulae:
ANH(CH COOM and AN (CH COOM] 2 wherein A is selected from the group of aliphatic hydrocarbon radicals and aliphatic acyl radicals of 8-20 carbon atoms, x=12 and M is a cation which will contribute to the water solubility of the coating aid.
8. A composition adapted to the coating out of layers for photographic products comprising in an aqueous system gelatin as a hydrophilic colloid, poly-alpha-methylallyl-N-guanidylketimine as the mordant, yellow sulfonated benZoXaZole-pyrazolone as the acid dye and as the coating aid sodium N-coco-beta-aminopropionate.
References Cited UNITED STATES PATENTS 2,240,471 4/1941 Swan 96-109 XR 2,882,156 4/1959 Minsk 96-84 3,016,306 1/1962 Mader et a1. 96-84 XR 3,133,816 5/1964 Ben-Ezra 96-94 3,142,568 7/1964 Nottorf 96-87 3,282,699 11/ 1966 Jones et al. 96-84 3,306,749 2/ 1967 Knox et a1 96-94 NORMAN G. TORCHIN, Primary Examiner.
I. TRAVIS BROWN, Examiner.
R. H. SMITH, Assistant Examiner.
Claims (2)
1. A COMPOSITION ADAPTED TO THE COATING OUT OF LAYERS FOR PHOTOGRAPHIC PRODUCTS COMPRISING IN AN AQUEOUS SYSTEM A HYDROPHILIC COLLOID, A POLYMERIC MORDANT HAVING RECURRING BASIC GROUPS, AN ACID DYE AND A COATING AID SELECTED FROM THE GROUP CONSISTING OF THE COMPOUNDS HAVING THE FOLLOWING GENERAL FORMULAE:
2. A PHOTOGRAPHIC ELEMENT HAVING AS A LAYER THEREIN A MIXTURE OF A HYDROPHILIC COLLOID, A POLYMERIC MORDANT HAVING RECURRING BASIC GROUPS, AN ACID DYE AND A COATING AID SELECTED FROM THE GROUP CONSISTING OF THE COMPOUNDS HAVING THE FOLLOWING GENERAL FORMULAE:
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US418881A US3408193A (en) | 1964-12-16 | 1964-12-16 | Coating compositions for the coating out of anionic mordant-acid dye layers |
| FR42329A FR1460235A (en) | 1964-12-16 | 1965-12-15 | New coating compositions and their applications, in particular, in photography |
| DE19651472880 DE1472880A1 (en) | 1964-12-16 | 1965-12-15 | Coating compound for the production of dye-mordant layers on photographic materials |
| GB53383/65A GB1124490A (en) | 1964-12-16 | 1965-12-16 | Photographic material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US418881A US3408193A (en) | 1964-12-16 | 1964-12-16 | Coating compositions for the coating out of anionic mordant-acid dye layers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3408193A true US3408193A (en) | 1968-10-29 |
Family
ID=23659937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US418881A Expired - Lifetime US3408193A (en) | 1964-12-16 | 1964-12-16 | Coating compositions for the coating out of anionic mordant-acid dye layers |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3408193A (en) |
| DE (1) | DE1472880A1 (en) |
| FR (1) | FR1460235A (en) |
| GB (1) | GB1124490A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3542581A (en) * | 1968-11-05 | 1970-11-24 | Eastman Kodak Co | Method of de-aggregating oxonol dye-containing gelatin layers |
| US4626497A (en) * | 1979-05-18 | 1986-12-02 | Ciba-Geigy Ag | Process for the production of colored photographic polymer images |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2240471A (en) * | 1940-03-07 | 1941-04-29 | Eastman Kodak Co | Photographic gelatin layer containing a n-acylated amino acid |
| US2882156A (en) * | 1955-12-19 | 1959-04-14 | Eastman Kodak Co | Basic mordants derived from the reaction of carbonyl containing polymers and aminoguanidine and their use |
| US3016306A (en) * | 1957-11-25 | 1962-01-09 | Eastman Kodak Co | Yellow filter layers for multi-layer photographic color elements |
| US3133816A (en) * | 1960-07-15 | 1964-05-19 | Gen Aniline & Film Corp | Photographic coating formulation |
| US3142568A (en) * | 1961-03-13 | 1964-07-28 | Du Pont | Photographic emulsions, elements, and processes |
| US3282699A (en) * | 1962-01-22 | 1966-11-01 | Eastman Kodak Co | Photographic elements containing bleachable mordanted dye layers |
| US3306749A (en) * | 1962-09-20 | 1967-02-28 | Eastman Kodak Co | Gelatin coating compositions |
-
1964
- 1964-12-16 US US418881A patent/US3408193A/en not_active Expired - Lifetime
-
1965
- 1965-12-15 DE DE19651472880 patent/DE1472880A1/en active Pending
- 1965-12-15 FR FR42329A patent/FR1460235A/en not_active Expired
- 1965-12-16 GB GB53383/65A patent/GB1124490A/en not_active Expired
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2240471A (en) * | 1940-03-07 | 1941-04-29 | Eastman Kodak Co | Photographic gelatin layer containing a n-acylated amino acid |
| US2882156A (en) * | 1955-12-19 | 1959-04-14 | Eastman Kodak Co | Basic mordants derived from the reaction of carbonyl containing polymers and aminoguanidine and their use |
| US3016306A (en) * | 1957-11-25 | 1962-01-09 | Eastman Kodak Co | Yellow filter layers for multi-layer photographic color elements |
| US3133816A (en) * | 1960-07-15 | 1964-05-19 | Gen Aniline & Film Corp | Photographic coating formulation |
| US3142568A (en) * | 1961-03-13 | 1964-07-28 | Du Pont | Photographic emulsions, elements, and processes |
| US3282699A (en) * | 1962-01-22 | 1966-11-01 | Eastman Kodak Co | Photographic elements containing bleachable mordanted dye layers |
| US3306749A (en) * | 1962-09-20 | 1967-02-28 | Eastman Kodak Co | Gelatin coating compositions |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3542581A (en) * | 1968-11-05 | 1970-11-24 | Eastman Kodak Co | Method of de-aggregating oxonol dye-containing gelatin layers |
| US4626497A (en) * | 1979-05-18 | 1986-12-02 | Ciba-Geigy Ag | Process for the production of colored photographic polymer images |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1460235A (en) | 1966-11-25 |
| DE1472880A1 (en) | 1969-03-06 |
| GB1124490A (en) | 1968-08-21 |
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