US3650759A - Silver halide emulsion containing 1.2-glycol as sensitizer and antifoggant - Google Patents
Silver halide emulsion containing 1.2-glycol as sensitizer and antifoggant Download PDFInfo
- Publication number
- US3650759A US3650759A US840477A US3650759DA US3650759A US 3650759 A US3650759 A US 3650759A US 840477 A US840477 A US 840477A US 3650759D A US3650759D A US 3650759DA US 3650759 A US3650759 A US 3650759A
- Authority
- US
- United States
- Prior art keywords
- silver halide
- group
- compound
- photographic
- 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
- 229910052709 silver Inorganic materials 0.000 title claims abstract description 64
- 239000004332 silver Substances 0.000 title claims abstract description 64
- -1 Silver halide Chemical class 0.000 title claims abstract description 63
- 239000000839 emulsion Substances 0.000 title claims abstract description 49
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 45
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 claims description 10
- 230000005070 ripening Effects 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 5
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 claims description 4
- 229940015975 1,2-hexanediol Drugs 0.000 claims description 3
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 claims description 3
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- YFBMUIMQJYESPZ-UHFFFAOYSA-N 3-phenoxy-1,2-propanediol Natural products C1C(OC(C)=O)CCC2(C)C3=CCC4(C)C(C(C)CCC(CC)C(C)C)CCC4(C)C3CCC21 YFBMUIMQJYESPZ-UHFFFAOYSA-N 0.000 claims 3
- FNQIYTUXOKTMDM-UHFFFAOYSA-N 3-phenoxypropane-1,2-diol Chemical compound OCC(O)COC1=CC=CC=C1 FNQIYTUXOKTMDM-UHFFFAOYSA-N 0.000 claims 3
- JHWQMXKQJVAWKI-UHFFFAOYSA-N UNPD187286 Natural products OCC(O)CC1=CC=CC=C1 JHWQMXKQJVAWKI-UHFFFAOYSA-N 0.000 claims 3
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 claims 2
- 230000035945 sensitivity Effects 0.000 abstract description 15
- 206010070834 Sensitisation Diseases 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 230000008313 sensitization Effects 0.000 description 7
- 239000000654 additive Substances 0.000 description 6
- 239000013068 control sample Substances 0.000 description 6
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 6
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 229940037003 alum Drugs 0.000 description 3
- 229920002301 cellulose acetate Polymers 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 3
- 229930182490 saponin Natural products 0.000 description 3
- 150000007949 saponins Chemical class 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- CBEQRNSPHCCXSH-UHFFFAOYSA-N iodine monobromide Chemical compound IBr CBEQRNSPHCCXSH-UHFFFAOYSA-N 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- XEIPQVVAVOUIOP-UHFFFAOYSA-N [Au]=S Chemical compound [Au]=S XEIPQVVAVOUIOP-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal 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
- G03C1/08—Sensitivity-increasing substances
-
- 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
- G03C1/08—Sensitivity-increasing substances
- G03C1/10—Organic substances
-
- 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
- G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
Definitions
- ABSTRACT A photographic silver halide light-sensitive emulsion is enhanced in sensitivity without an attendant increase in fog by addition to the silver halide emulsion of a 1,2-glycol of the wherein R R and R represent a hydrogen atom or an alkyl group, and R represents a hydrogen atom, an alkyl group. an aryl group, an alkoxyalkyl group, an aryloxyalkyl group. or e jl lssmyL rs rz-Am I. W
- the present invention relates to a photographic silver halide light-sensitive element and a method for preparing it. More particularly, the present invention relates to a photographic silver halide light-sensitive element having a silver halide emulsion layer containing a compound having a sensitizing action and an antifogging action simultaneously and also a method for the preparation thereof.
- the silver halide emulsion is subjected to chemical ripening, i.e., a sulfur sensitization, reduction sensitization, or gold sensitization.
- chemical ripening i.e., a sulfur sensitization, reduction sensitization, or gold sensitization.
- sensitizers can be added to the photographic emulsion after the application of chemical ripening.
- an object of the present invention is to provide a photographic silver halide emulsion which is sensitized without an attendant increase in fog.
- Another object of this invention is to provide photographic silver halide light-sensitive element having a photographic layer of the above photographic silver halide emulsion.
- Still another object of this invention is to provide a method of preparing the aforesaid photographic silver halide emulsion and also the aforesaid photographic silver halide light-sensitive element.
- the above compound used in this invention acts as a sensitizer and an antifoggant simultaneously and gives an excel lent sensitizing effect as compared with conventional sensitizers as well as reduces the formation of fog which has been considered to be increased with an increase in sensitivity. Accordingly, the silver halide emulsion containing the compound and the photographic silver halide light-sensitive element having the silver halide emulsion layer of this invention are excellent in such points that the sensitivity is high and the formation of fog is less as compared with conventional emulsions and elements.
- the compound of this invention may be added to a silver halide emulsion subjected to chemical ripening together with other additives as usually practiced or may be added to a silver halide emulsion subjected to physical ripening by a conventional method. However, better results can be obtained when the compound is added to a silver halide emulsion at the beginning of chemical ripening.
- the amount of the compound shown above to be added to a silver halide emulsion is influenced by a desired effect, the degree of ripening thereof, the kind of the silver halide emulsion and the like, but in general, preferably about 2-100 g., particularly 5-50 g. of the 1,2-glycol are added per mole of silver halide in the emulsion.
- the compound can also be used together with photographic additives usually employed, such as, an optical sensitizer, a wetting agent, a hardening agent, a
- the coating compositions thus prepared were applied to cellulose acetate films so that the amount of silver coated became 45 mg./ l sq. cm. and dried.
- a control sample was prepared by the aforesaid procedure but without adding the compound of this invention.
- the photographic light-sensitive films thus prepared were exposed by using a NSG-ll sensitometer and developed for 7 minutes at 20 C. in a developer having the following compositron:
- EXAMPLE 2 Two separate silver iodobromide emulsions were prepared (1.5 mole percent Agl and 150 g. of gelatin per one mole of silver iodobromide) for high-speed X-ray photographic film, and 1,2-hexanediol (Compound (g)), and l-phenyl-l,2- ethanediol (Compound (h)) were added to the respective emulsions. These emulsions were then subjected to second ripening by sulfur-gold sensitization at 53 C.
- the silver halide emulsions thus prepared were applied to a cellulose acetate film so that the amount of silver applied became 55 mg./100 sq. cm. and dried.
- a control sample was prepared by the same procedure as above without employing the compound of this invention.
- the photographic films thus obtained were exposed by using a NSG-ll sensitometer and developed for 4 minutes at C. in a developer having the composition as follows:
- the photographic silver halide emulsion containing the additive of this invention has a higher sensitivity and less fog than the control sample.
- the photographic silver halide emulsion of this invention prepared above had a high sensitivity and gave less fog.
- said compound is selected from the group consisting of 2,3-butanediol, 1,2-butanediol, pinacol, 1,2-h'exanediol, 1-phenyl-l,2-ethanediol, 3-m-octyl-oxyl ,2- propanediol, 3-aryloxy-l,2-propanedio1, 3-phenoxy-l,2- propanediol
- a process for preparing silver halide photographic emulsion which comprises adding a compound represented by the general formula wherein R,, R and R each represents one member selected from the group consisting of a hydrogen atom and an alkyl group, and R represents one member selected from the group consisting of a hydrogen atom, an alkyl group, an aryl group, an alkoxyalkyl group, an aryloxyalkyl group and an allyloxyalkyl group.
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Organic Chemistry (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 |
|---|---|---|---|
| JP4802168 | 1968-07-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3650759A true US3650759A (en) | 1972-03-21 |
Family
ID=12791642
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US840477A Expired - Lifetime US3650759A (en) | 1968-07-09 | 1969-07-09 | Silver halide emulsion containing 1.2-glycol as sensitizer and antifoggant |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3650759A (enrdf_load_stackoverflow) |
| BE (1) | BE735798A (enrdf_load_stackoverflow) |
| FR (1) | FR2012566A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1252960A (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3898089A (en) * | 1972-11-28 | 1975-08-05 | Fuji Photo Film Co Ltd | Silver halide photographic material containing a polyhydric alcohol, a glyoxal and a triazine |
| US4357419A (en) * | 1981-04-02 | 1982-11-02 | Minnesota Mining And Manufacturing Company | Covering power in films |
| US4840888A (en) * | 1986-01-22 | 1989-06-20 | Konishiroku Photo Industry Co., Ltd. | Light-sensitive silver halide photographic material |
| US5102782A (en) * | 1990-12-11 | 1992-04-07 | E. I. Du Pont De Nemours And Company | Photographic film with improved speed to fog ratio |
| USH1091H (en) | 1988-08-09 | 1992-08-04 | Konica Corporation | Light-sensitive silver halide photographic material |
| US5185240A (en) * | 1989-08-11 | 1993-02-09 | Fuji Photo Film Co., Ltd. | Silver halide photographic material |
| US5589325A (en) * | 1993-11-01 | 1996-12-31 | Fuji Photo Film Co., Ltd. | Silver halide photographic material |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3068102A (en) * | 1961-03-22 | 1962-12-11 | Eastman Kodak Co | Photographic emulsions sensitized with sulfite ester polymers |
| US3294540A (en) * | 1963-12-17 | 1966-12-27 | Eastman Kodak Co | Lith-type emulsions with block co-polymers |
-
1969
- 1969-07-08 GB GB1252960D patent/GB1252960A/en not_active Expired
- 1969-07-08 BE BE735798D patent/BE735798A/xx unknown
- 1969-07-08 FR FR6923178A patent/FR2012566A1/fr not_active Withdrawn
- 1969-07-09 US US840477A patent/US3650759A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3068102A (en) * | 1961-03-22 | 1962-12-11 | Eastman Kodak Co | Photographic emulsions sensitized with sulfite ester polymers |
| US3294540A (en) * | 1963-12-17 | 1966-12-27 | Eastman Kodak Co | Lith-type emulsions with block co-polymers |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3898089A (en) * | 1972-11-28 | 1975-08-05 | Fuji Photo Film Co Ltd | Silver halide photographic material containing a polyhydric alcohol, a glyoxal and a triazine |
| US4357419A (en) * | 1981-04-02 | 1982-11-02 | Minnesota Mining And Manufacturing Company | Covering power in films |
| US4840888A (en) * | 1986-01-22 | 1989-06-20 | Konishiroku Photo Industry Co., Ltd. | Light-sensitive silver halide photographic material |
| USH1091H (en) | 1988-08-09 | 1992-08-04 | Konica Corporation | Light-sensitive silver halide photographic material |
| US5185240A (en) * | 1989-08-11 | 1993-02-09 | Fuji Photo Film Co., Ltd. | Silver halide photographic material |
| US5102782A (en) * | 1990-12-11 | 1992-04-07 | E. I. Du Pont De Nemours And Company | Photographic film with improved speed to fog ratio |
| US5589325A (en) * | 1993-11-01 | 1996-12-31 | Fuji Photo Film Co., Ltd. | Silver halide photographic material |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1934626A1 (de) | 1970-05-27 |
| GB1252960A (enrdf_load_stackoverflow) | 1971-11-10 |
| BE735798A (enrdf_load_stackoverflow) | 1969-12-16 |
| FR2012566A1 (enrdf_load_stackoverflow) | 1970-03-20 |
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