US3576637A - Lith-type of emulsion containing pyrozolone - Google Patents
Lith-type of emulsion containing pyrozolone Download PDFInfo
- Publication number
- US3576637A US3576637A US721175A US3576637DA US3576637A US 3576637 A US3576637 A US 3576637A US 721175 A US721175 A US 721175A US 3576637D A US3576637D A US 3576637DA US 3576637 A US3576637 A US 3576637A
- Authority
- US
- United States
- Prior art keywords
- compound
- lith
- alkylene oxide
- silver halide
- type
- 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 abstract description 23
- -1 PYRAZOLONE COMPOUND Chemical class 0.000 abstract description 26
- 229910052709 silver Inorganic materials 0.000 abstract description 16
- 239000004332 silver Substances 0.000 abstract description 16
- 150000001875 compounds Chemical class 0.000 description 25
- 125000002947 alkylene group Chemical group 0.000 description 17
- 239000000463 material Substances 0.000 description 10
- 239000010410 layer Substances 0.000 description 8
- 208000015181 infectious disease Diseases 0.000 description 5
- 230000002458 infectious effect Effects 0.000 description 5
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 241001466767 Galathea perone Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 206010070834 Sensitisation Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 230000008313 sensitization Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical group OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- XYXNTHIYBIDHGM-UHFFFAOYSA-N ammonium thiosulfate Chemical compound [NH4+].[NH4+].[O-]S([O-])(=O)=S XYXNTHIYBIDHGM-UHFFFAOYSA-N 0.000 description 1
- UREVLELSVZQJTM-UHFFFAOYSA-N benzene-1,4-diol;formaldehyde Chemical compound O=C.OC1=CC=C(O)C=C1 UREVLELSVZQJTM-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- FDWREHZXQUYJFJ-UHFFFAOYSA-M gold monochloride Chemical compound [Cl-].[Au+] FDWREHZXQUYJFJ-UHFFFAOYSA-M 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 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
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/04—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances
- G03C1/043—Polyalkylene oxides; Polyalkylene sulfides; Polyalkylene selenides; Polyalkylene tellurides
-
- 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
-
- 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
- Y10S430/15—Lithographic emulsion
Definitions
- This invention relates to light-sensitive photographic silver halide materials and particularly to photographic printing materials of the lith-type.
- a light-sensitive photographic silver halide material which is used for halftone reproduction in the recent graphic arts is called as a lith-type film, for which are required various photographic properties including high image contrast, sharp halftone dots and good line image, broad latitude for development, high speed and high resolution.
- the object of this invention is to provide a light-sensitive photographic silver halide material which has excellent photographic properties at the initial stage of infectious development and good contrast and halftone dot quality even at the stage after a normal period of development.
- a light-sensitive silver halide photographic material comprising a support and a light-sensitive emulsion layer coated thereon, characterized by a compound of the general formula (wherein R is acylamino, arylamino, alkyl, aryl or aralkyl 15 radical and X is hydrogen atom or carboxyl or sulfonic group) is incorporated together with an alkylene oxide compound (molecular Weight GOO-8,000) in the lightsensitive emulsion layer or in the layer contiguous there- With Examples of pyrazolone compounds used in this invention include the following ones without limitation thereto.
- alkylene oxide compounds referred to therein may be included the condensation products of alkylene oxide with water, aliphatic alcohols, glycols, fatty acids, aliphatic amines, phenols, hexitol ring dehydration products, etc. These alkylene oxide compounds may be used singly or in combination.
- the amounts of the pyrazolone and alkylene oxide compounds to be added will vary depending on their types.
- the pyrazolone compound is used in an amount of 10 mg. to 10 g. per one mole of silver halide and the alkylene oxide compound used in an amount of 10 mg. to 10 g. per one mole of silver halide.
- the pyrozolone compound and the alkylene oxide compound may be added to the light-sensitive silver halide emulsion at any stage during the preparation of said emulsion. But the most preferable result is obtained when these compounds are added after ripening and before coating of said emulsion.
- the compounds to be added can be introduced in the form of a solution in aqueous sodium hydroxide or in an organic solvent such as methanol.
- the solution may be incorporated in a photographic layer adjacent to the emulsion layer, e.g. in a protective layer or an inter layer.
- any type of silver halide emulsions are usable.
- silver chloride, bromide and iodide emulsions or their mixtures are usable.
- these emulsions may be sensitized chemically by sulfur sensitization (with ammonium thiosulfate), gold sensitization (with gold chloride) or optical sensitization (with cyan dye or merocyan dye).
- Suitable hardening agents and surface active agents can be added to the emulsion.
- the silver halide is dispersed in hydrophilic materials used as binders such as gelatine or polyvinyl alcohol.
- the material of the invention can be treated with a conventionally known lith-developer.
- a light-sensitive silver halide photographic material of this invention is useful as a lith-type film which has good image contrast, sharp ment and high photographic speed and high resolution.
- the present invention is illustrated in the following example but not limited thereto.
- the individual film to be tested was brought into close contact with a step-wedge and then subjected to exposure to irradiation through the stepwedge from an iodine lamp of 200 volt and 1 kw. as a light source.
- the exposed film was then treated with a developing solution described hereafter.
- relative speed was determined at the point where the density is 1.0.
- halftone dot quality In the evaluation of halftone dot quality, the film to be tested was brought into contact with a magenta contact screen under suction in vacuum. Exposure to light and development were carried out in the same manner as in the above-mentioned sensitometry. The amount of the light exposure, however, was regulated so as to produce dot size 40-60%. The halftone dots formed were visually inspected by means of a microscope. Rating of halftone dot quality was made in term of sharpness. Rating 5 indicates that the dots have the highest sharpness, while rating 1 does that the dots have the lowest sharpness. Halftone dots between these two ratings are classified to ratings 4, 3 and 2.
- Control 2 Polyethylene glycol (molecular weight: 1,000) 1 3 Alkylene oxide Polyethylene glycol compound alone. weight: 4,000), g 0. 05 4.. Condensate of ethylene oxide (molecular weight: 900) and lauryl alcohol, g 0. 4 6 Pyrazolone Compound 3, g 0. 1 6 compound Compound 5, g 0. 05 7 alone. Compound 7, g 0. 08 Polyethylene glycol 4,000), g 0. 05 8 Joint use of Compound 3, g 0. 1
- alkylene oxide 9 compound and Polyethylene glycol (M.W. 1,000), g 1 pyrazolone Compound 5, g 0. 05 compound.
- Developing treatment was carried out at 20 C. stepwise for 1.5 minutes, 2.5 minutes and 3.5 minutes by using the developing solution having the following composition:
- the Samples 2, 3 and 4 to which only an alkylene oxide compound is added show decrease in sensitivity and halftone dot quality in the initial development.
- the samples 5, 6 and 7 to which only a pyrazolone compound is added show less decrease in sensitivity than that observed in the above alkylene oxide addition samples, whereas the halftone dot quality decreased.
- sensitivity and halftone dot quality of the samples 8, 9 and 10 in which an alkylene oxide derivative and a pyrazolone compound are included together according to the present invention are remarkably recovered.
- the halftone dot quality of these samples do not show any decrease even after the treatment for 3.5 minutes.
- a light-sensitive photographic silver halide material of the lith-type which comprises a support and a lightsensitive photographic silver halide emulsion layer coated thereon, a pyrazolone compound of the formula wherein R is an acylamino, arylamino, alkyl, aryl or aralkyl group and X is hydrogen atom, a carboxyl or a sulfonic acid group; and a condensation product of an alkylene oxide and a compound selected from the group consisting of water, an aliphatic alcohol, a glycol, an aliphatic acid, an aliphatic amine, a phenol and a hexitol ring dehydration product; said pyrazolone compound and condensation product are both contained in the emulsion layer or a layer adjacent thereto.
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2478167 | 1967-04-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3576637A true US3576637A (en) | 1971-04-27 |
Family
ID=12147708
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US721175A Expired - Lifetime US3576637A (en) | 1967-04-20 | 1968-04-15 | Lith-type of emulsion containing pyrozolone |
Country Status (4)
Country | Link |
---|---|
US (1) | US3576637A (en:Method) |
BE (1) | BE713912A (en:Method) |
DE (1) | DE1772233A1 (en:Method) |
GB (1) | GB1195134A (en:Method) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005046679A1 (en) * | 2003-11-04 | 2005-05-26 | Avidex Limited | Immuno inhibitory pyrazolone compounds |
US20090062289A1 (en) * | 2004-08-09 | 2009-03-05 | Avidex Limited | Immunomodulating oxopyrrazolocinnolines as cd 80 inhibitors |
US20090221590A1 (en) * | 2006-02-22 | 2009-09-03 | Medigene Limited | Salt of cd 80 antagonist |
US20090312334A1 (en) * | 2003-03-14 | 2009-12-17 | Medigene Limited | Immunomodulating Heterocyclic Compounds |
-
1968
- 1968-04-15 US US721175A patent/US3576637A/en not_active Expired - Lifetime
- 1968-04-18 DE DE19681772233 patent/DE1772233A1/de active Granted
- 1968-04-19 BE BE713912D patent/BE713912A/xx unknown
- 1968-04-19 GB GB18712/68A patent/GB1195134A/en not_active Expired
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20090312334A1 (en) * | 2003-03-14 | 2009-12-17 | Medigene Limited | Immunomodulating Heterocyclic Compounds |
US8309552B2 (en) | 2003-03-14 | 2012-11-13 | Medigene Ag | Immunomodulating heterocyclic compounds |
WO2005046679A1 (en) * | 2003-11-04 | 2005-05-26 | Avidex Limited | Immuno inhibitory pyrazolone compounds |
US20070213345A1 (en) * | 2003-11-04 | 2007-09-13 | Avidex Limited | Immuno Inhibitory Pyrazolone Compounds |
US7816361B2 (en) | 2003-11-04 | 2010-10-19 | Medigene Limited | Immuno inhibitory pyrazolone compounds |
US20100331342A1 (en) * | 2003-11-04 | 2010-12-30 | Medigene Limited | Immuno Inhibitory Pyrazolone Compounds |
US8163757B2 (en) | 2003-11-04 | 2012-04-24 | Medigene Ag | Immuno inhibitory pyrazolone compounds |
US20090062289A1 (en) * | 2004-08-09 | 2009-03-05 | Avidex Limited | Immunomodulating oxopyrrazolocinnolines as cd 80 inhibitors |
US7932253B2 (en) | 2004-08-09 | 2011-04-26 | Medigene Ag | Immunomodulating oxopyrrazolocinnolines as CD80 inhibitors |
US20090221590A1 (en) * | 2006-02-22 | 2009-09-03 | Medigene Limited | Salt of cd 80 antagonist |
Also Published As
Publication number | Publication date |
---|---|
GB1195134A (en) | 1970-06-17 |
BE713912A (en:Method) | 1968-09-16 |
DE1772233A1 (de) | 1972-01-05 |
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