US3203800A - Photographic material comprising a silver halide emulsion containing an anti-bronzing agent - Google Patents
Photographic material comprising a silver halide emulsion containing an anti-bronzing agent Download PDFInfo
- Publication number
- US3203800A US3203800A US249615A US24961563A US3203800A US 3203800 A US3203800 A US 3203800A US 249615 A US249615 A US 249615A US 24961563 A US24961563 A US 24961563A US 3203800 A US3203800 A US 3203800A
- Authority
- US
- United States
- Prior art keywords
- silver
- mercapto
- silver halide
- halide emulsion
- emulsion
- 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
- 239000000839 emulsion Substances 0.000 title claims description 35
- 239000000463 material Substances 0.000 title claims description 22
- -1 silver halide Chemical class 0.000 title description 29
- 229910052709 silver Inorganic materials 0.000 title description 26
- 239000004332 silver Substances 0.000 title description 26
- 239000003795 chemical substances by application Substances 0.000 title description 8
- 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 claims description 13
- 229940009188 silver Drugs 0.000 description 25
- 150000001875 compounds Chemical class 0.000 description 16
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 6
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229910001961 silver nitrate Inorganic materials 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 229910001864 baryta 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000005070 ripening Effects 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 1
- 241000206607 Porphyra umbilicalis Species 0.000 description 1
- 229910021612 Silver iodide Inorganic materials 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001246 colloidal dispersion Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
- C07C319/12—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols by reactions not involving the formation of mercapto 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
- 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
- G03C1/35—Antiplumming agents, i.e. antibronzing agents; Toners
- G03C1/355—Organic derivatives of bivalent sulfur, selenium or tellurium
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/13—Antibronze agent or process
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/136—Coating process making radiation sensitive element
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/139—Defect coating
Definitions
- the images obtained in light-sensitive silver halide emulsion layers often undergo changes during processing among others during hot glazing or mechanical drying, at high temperature. During these treatments loss of density occurs easily by the so-called bronzing of the silver image.
- R represents an aryl group or a substituted aryl group
- R represents a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group or a substituted aryl p,
- R and R represent a hydrogen atom, a lower alkyl group or a substituted lower alkyl group
- n a positive integer from 1 to 5
- the disadvantages caused by hot glazing or mechanical drying are prevented.
- Suitable compounds corresponding to the above general formula are e.g.:
- the light-sensitive silver halide emulsion wherein compounds according to the present invention can be incorporated can be any silver halide emulsion such as a gelatinosilver chloride emulsion, a gelatino-silver chloro-bromide emulsion, a gelatino-silver chloroiodide emulsion, a gelatino-silver bromide emulsion, a gelatino-silver bromoiodide emulsion, and a gelation-silver chlorobro
- the compounds according to the present invention can be added during any stage of the preparation of the emulsion, e.g. during the formation of the silver halide or during the physical or chemical ripening, but preferably after the chemical ripening.
- the amount, in which the compounds according to the present invention may be added depends on the emulsion used but it generally varies from 2 to 20 g. per 1000 g. of silver nitrate.
- the compounds according to the present invention are present in the light-sensitive composition in the form of a colloidal dispersion.
- the compounds according to the present invention in a hydrophilic layer adjacent to the light-sensitive layer e.g. in the covering layer, or in another layer from which, during fixation, they can e.g. diffuse to the silver halide emulsion layer.
- concentration in which the compounds according to the invention are incorporated into these layers is mostly the same as or slightly higher than their concentration when added to the light-sensitive layer.
- the compounds according to the invention are sometimes incorporated into a processing bath e.g. in the fixing bath.
- poly(N-vinylpyrrolidone) gives as anti-bronzing agent still better results.
- poly(N-vinylpyrrolidone) can be incorporated into the light-sensitive laver and/or into an other water permeable layer at the same side of the support as the light-sensitive layer, in a concentration which preferably varies from 20 to 80 g. per mole of silver halide.
- Example 1 To an ammoniacal gelatino-silver bromoiodide emulsion containing 3.5 mol percent of silver iodide based on the total amount of silver halide and having a medium gradation are added per mole of silver halide 1.9 g. of the silver salt of a-mercapto-butyric acid-p-toluidide in the form of a dispersion.
- This emulsion is applied on a baryta-coated paper support in such a way, the light-sensitive layer contains per sq. m. an amount of silver halide equivalent to 2 g. of silver nitrate.
- On this emulsion layer a gelatin-containing convering layer is coated.
- This material is exposed under a step-wedge, developed, fixed and rinsed. Then it is subjected to high glossing by pressing its image side against a heated polished metal surface. The reflection densities are measured by means of a MacBeth densitometer before and after subjecting the material to high glossing. The following results are obtained:
- Example 2 Three materials are prepared starting from an ammoniacal gelatino-silver bromoiodide emulsion as described in Example 1.
- the first material the comparison material
- no anti-bronzing agent is added to the emulsion.
- the second and the third material respectively of 0.45 g. of the silver salt of a-rnercapto-butyric acid-p-toluidide and 0.45 g. of the silver salt of ,B-mercapto-propionic acid-ptoluidide are added to the emulsion per mol of silver halide.
- a photographic material comprising a support and at least one light-sensitive silver halide emulsion layer and containing the silver salt of a-mercapto-butyric acid-ptoluidide in at least one water permeable layer which is situated at the same side of the support as the lightsensitive silver halide emulsion layer.
- a photographic material comprising a support and at least one light-sensitive silver halide emulsion layer and containing the silver salt of fl-mercapto-propionic acid-p-toluidide in at least one water-permeable layer which is situated at the same side of the support as the light-sensitive silver halide emulsion layer.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United States Patent 3,203,800 PHOTOGRAPHIC MATERIAL COMPRISING A SIL- VER HALIDE EMULSION CONTAINING AN ANTI-BRONZING AGENT Jozef Frans Willenis, Hendrik Adolf Pattijn, and Gerard Michiel Sevens, Wilrijk-Antwerp, Belgium, assignors to Gevaert Photo-Producten N.V., Mortsel-Antwerp, Belgium, a company of Belgium No Drawing. Filed Jan. 7, 1963, Ser. No. 249,615 Claims priority, application Belgium, Jan. 5, 1962, 41,269, Patent 612,311 4 Claims. (Cl. 96-67) This invention relates to photographic material which is protected against bronzing caused by hot glazing or mechanical drying.
The images obtained in light-sensitive silver halide emulsion layers often undergo changes during processing among others during hot glazing or mechanical drying, at high temperature. During these treatments loss of density occurs easily by the so-called bronzing of the silver image.
It is known to add small amounts of chemical compounds to light-sensitive materials containing silver halide or to certain processing baths in order to avoid decrease of density as a result of high glossing.
. In addition to the fact that these compounds do not completely counteract bronzing, they still show other disadvantages when being added to a silver halide emulsion.
The most important disadvantage is their mostly very strong desensitizing action.
It has now been found that by adding compounds according to the following general formula:
R represents an aryl group or a substituted aryl group,
R represents a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group or a substituted aryl p,
Each of R and R (same or ditferent) represent a hydrogen atom, a lower alkyl group or a substituted lower alkyl group, and
n represents a positive integer from 1 to 5,
to the light-sensitive silver halide emulsion layer and/or to at least one water-permeable layer of the light-sensitive material at the same side of the support as said emulsion layer, the disadvantages caused by hot glazing or mechanical drying are prevented.
Contrary to suchlike compounds with a free mercapto function, these compounds have no desensitizing action on the silver halide emulsion.
Suitable compounds corresponding to the above general formula are e.g.:
silver salt of a-mercapto butyric acid-p-toluidide silver salt of fl-mercapto-propionic acid-p-toluidide @NH-G O-CHr-SAg silver salt of a-mercapto-acetanilide 3,203,800 Patented Aug. 31, 1965 ice silver :salt of a-mercapto-butyric acid-l-naphthalide silver salt of a-mercapto-acetic acid-Z-naphthalide silver salt of N-phenyl-a-mercapto-butyric acid-anilide silver salt of a-mercapto-propionic acid-p-toluidide silver salt of a-mercapto-isobutyric acid-p-toluidide The light-sensitive silver halide emulsion wherein compounds according to the present invention can be incorporated can be any silver halide emulsion such as a gelatinosilver chloride emulsion, a gelatino-silver chloro-bromide emulsion, a gelatino-silver chloroiodide emulsion, a gelatino-silver bromide emulsion, a gelatino-silver bromoiodide emulsion, and a gelation-silver chlorobromoiodide emulsion. The emulsion can be sensitized chemically as well as optically. It may moreover contain all known additives such as anti-fogging agents, stabilizers, hardening agents, softening agents and dispersiing agents.
The compounds according to the present invention can be added during any stage of the preparation of the emulsion, e.g. during the formation of the silver halide or during the physical or chemical ripening, but preferably after the chemical ripening.
The amount, in which the compounds according to the present invention may be added depends on the emulsion used but it generally varies from 2 to 20 g. per 1000 g. of silver nitrate.
The compounds according to the present invention are present in the light-sensitive composition in the form of a colloidal dispersion.
When using the compounds according to the present invention, there is no loss in sensitivity or contrast of the photographic material, whereas the use of the compounds in their free mercapto form or as alkaline metal or ammonium salt would cause a considerable loss in sensitivity.
It is also possible to incorporate the compounds according to the present invention in a hydrophilic layer adjacent to the light-sensitive layer e.g. in the covering layer, or in another layer from which, during fixation, they can e.g. diffuse to the silver halide emulsion layer. The concentration in which the compounds according to the invention are incorporated into these layers is mostly the same as or slightly higher than their concentration when added to the light-sensitive layer.
The compounds according to the invention are sometimes incorporated into a processing bath e.g. in the fixing bath.
The combination of at least one of the compounds according to this invention with poly(N-vinylpyrrolidone) gives as anti-bronzing agent still better results. In that case poly(N-vinylpyrrolidone) can be incorporated into the light-sensitive laver and/or into an other water permeable layer at the same side of the support as the light-sensitive layer, in a concentration which preferably varies from 20 to 80 g. per mole of silver halide.
The following are examples illustrating the properties of photographic materials containing anti-bronzing agents according to the present invention.
Example 1 To an ammoniacal gelatino-silver bromoiodide emulsion containing 3.5 mol percent of silver iodide based on the total amount of silver halide and having a medium gradation are added per mole of silver halide 1.9 g. of the silver salt of a-mercapto-butyric acid-p-toluidide in the form of a dispersion. This emulsion is applied on a baryta-coated paper support in such a way, the light-sensitive layer contains per sq. m. an amount of silver halide equivalent to 2 g. of silver nitrate. On this emulsion layer a gelatin-containing convering layer is coated. This material is exposed under a step-wedge, developed, fixed and rinsed. Then it is subjected to high glossing by pressing its image side against a heated polished metal surface. The reflection densities are measured by means of a MacBeth densitometer before and after subjecting the material to high glossing. The following results are obtained:
Maximum density After subjecting to high glossing Before subjecting to high glossing Example 2 Three materials are prepared starting from an ammoniacal gelatino-silver bromoiodide emulsion as described in Example 1. In the preparation of the first material (the comparison material), no anti-bronzing agent is added to the emulsion. In the preparation of the second and the third material, respectively of 0.45 g. of the silver salt of a-rnercapto-butyric acid-p-toluidide and 0.45 g. of the silver salt of ,B-mercapto-propionic acid-ptoluidide are added to the emulsion per mol of silver halide. Moreover, in the preparation of the three emulsions, 60 g. of poly(N-vinylpyrrolidone) are added per mol of silver halide. baryta-coated paper supports in such a way, that the lightsensitive layer contains per sq. m. an amount of silver The emulsions are applied to halide equivalent to 2.2 g. of silver nitrate. On the emulsion layers gelatin-containing covering layers are coated.
The three materials thus obtained are then treated in the same way as in Example 1. The results are the following.
Maximum density Before sub- After subjecting to jecting to high glossing high glossing First material (comparison material) 2. 04 1. 03 Second material 2. 10 2. 06 Third material 2. 11 2. 02
- of the support as the light-sensitive silver-halide emulsion layer.
2. A photographic material comprising a support and at least one light-sensitive silver halide emulsion layer and containing the silver salt of a-mercapto-butyric acid-ptoluidide in at least one water permeable layer which is situated at the same side of the support as the lightsensitive silver halide emulsion layer.
3. A photographic material comprising a support and at least one light-sensitive silver halide emulsion layer and containing the silver salt of fl-mercapto-propionic acid-p-toluidide in at least one water-permeable layer which is situated at the same side of the support as the light-sensitive silver halide emulsion layer.
4. The photographic material of claim 1 wherein the water-permeable layer contains poly(N-vinylpyrrolidone).
References Cited by the Examiner UNITED STATES PATENTS 3,080,230 3/ 63 Haydn et al. 96--95 FOREIGN PATENTS 1,090,385 3/55 France.
794,637 5/58 Great Britain. 607,639 10/60 Canada. 1,119,119 12/61 Germany.
NORMAN G. TORCHIN, Primary Examiner.
Claims (1)
1. A PHOTOGRAPHIC MATERIAL COMPRISING A SUPPORT AND AT LEAST ONE LIGHT-SENSITIVE SILVER-HALIDE EMULSION LAYER AND CONTAINING THE SILVER SALT OF A MEMBER OF THE GROUP CONSISTING OF A-MERCAPTO BUTYRIC ACID-P-TOLUIDIED, BMERCAPTO-PROPIONIC ACID-P-TOLUDIDE, A-MERCAPTO-ACENTANILIDE, A-MERCAPTOBUTYRIC ACID-L-NAPHTHALIDE, A-MERCAPTOACTEIC ACID-2-NAPHTHALIDE N-PHENYL-A-NERCPTO-BUTYRIC ACID-ANILIDE, A-MERCAPTO-PROPIONIC ACID-P-TOLUIDIDE, AND A-MERCAPTO-ISOBUTYRIC ACID-P-TOLUIDIDE IN AT LEAST ONE WATER-PERMEABLE LAYER WHICH IS SITUATED AT THE SAME SIDE OF THE SUPPORT AS THE LIGHT-SENSITVE SILVER-HALIDE EMULSION LAYER.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE2041269 | 1962-01-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3203800A true US3203800A (en) | 1965-08-31 |
Family
ID=3864762
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US249595A Expired - Lifetime US3282696A (en) | 1962-01-05 | 1963-01-07 | Photographic silver halide elements containing anti-bronzing agents |
| US249615A Expired - Lifetime US3203800A (en) | 1962-01-05 | 1963-01-07 | Photographic material comprising a silver halide emulsion containing an anti-bronzing agent |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US249595A Expired - Lifetime US3282696A (en) | 1962-01-05 | 1963-01-07 | Photographic silver halide elements containing anti-bronzing agents |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US3282696A (en) |
| BE (1) | BE612311A (en) |
| DE (2) | DE1155330B (en) |
| GB (2) | GB1024035A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1203051A (en) * | 1967-02-15 | 1970-08-26 | Agfa Gevaert Nv | Improvements in or relating to photographic light-sensitive silver halide materials |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1090385A (en) * | 1949-03-02 | 1955-03-30 | Kodak Pathe | Improvements in photography and products for their realization |
| GB794637A (en) * | 1955-06-21 | 1958-05-07 | Kodak Ltd | Improvements in photographic emulsions |
| CA607639A (en) * | 1960-10-25 | Dersch Fritz | Photographic materials and method of producing the same | |
| DE1119119B (en) * | 1957-09-26 | 1961-12-07 | Gen Aniline & Film Corp | Photographic material with photosensitive halide silver emulsion layer and polyalkylene oxide content |
| US3080230A (en) * | 1956-02-18 | 1963-03-05 | Agfa Ag | Photographic stratum transfer process and element therefor |
-
0
- BE BE612311D patent/BE612311A/xx unknown
-
1963
- 1963-01-04 GB GB486/63A patent/GB1024035A/en not_active Expired
- 1963-01-04 GB GB487/63A patent/GB1002329A/en not_active Expired
- 1963-01-04 DE DEG36782A patent/DE1155330B/en active Pending
- 1963-01-04 DE DEG36781A patent/DE1155013B/en active Pending
- 1963-01-07 US US249595A patent/US3282696A/en not_active Expired - Lifetime
- 1963-01-07 US US249615A patent/US3203800A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA607639A (en) * | 1960-10-25 | Dersch Fritz | Photographic materials and method of producing the same | |
| FR1090385A (en) * | 1949-03-02 | 1955-03-30 | Kodak Pathe | Improvements in photography and products for their realization |
| GB794637A (en) * | 1955-06-21 | 1958-05-07 | Kodak Ltd | Improvements in photographic emulsions |
| US3080230A (en) * | 1956-02-18 | 1963-03-05 | Agfa Ag | Photographic stratum transfer process and element therefor |
| DE1119119B (en) * | 1957-09-26 | 1961-12-07 | Gen Aniline & Film Corp | Photographic material with photosensitive halide silver emulsion layer and polyalkylene oxide content |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1155013B (en) | 1963-09-26 |
| DE1155330B (en) | 1963-10-03 |
| GB1002329A (en) | 1965-08-25 |
| GB1024035A (en) | 1966-03-30 |
| US3282696A (en) | 1966-11-01 |
| BE612311A (en) |
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