US3630745A - THIAZOLO {8 5,4-c{9 ISOQUINOLINE AND THIAZOLO {8 4,5-c{9 IOSQUINOLINE AND DERIVATIVES AS ANTIFOGGANTS FOR PHOTOGRAPHIC LAYERS - Google Patents
THIAZOLO {8 5,4-c{9 ISOQUINOLINE AND THIAZOLO {8 4,5-c{9 IOSQUINOLINE AND DERIVATIVES AS ANTIFOGGANTS FOR PHOTOGRAPHIC LAYERS Download PDFInfo
- Publication number
- US3630745A US3630745A US864887A US3630745DA US3630745A US 3630745 A US3630745 A US 3630745A US 864887 A US864887 A US 864887A US 3630745D A US3630745D A US 3630745DA US 3630745 A US3630745 A US 3630745A
- Authority
- US
- United States
- Prior art keywords
- photographic
- silver halide
- isoquinoline
- emulsion
- thiazolo
- 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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- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 title abstract description 8
- -1 silver halide Chemical class 0.000 claims abstract description 65
- 239000000839 emulsion Substances 0.000 claims abstract description 58
- 229910052709 silver Inorganic materials 0.000 claims abstract description 58
- 239000004332 silver Substances 0.000 claims abstract description 58
- 150000001875 compounds Chemical class 0.000 claims description 29
- 239000003381 stabilizer Substances 0.000 claims description 21
- 230000000087 stabilizing effect Effects 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 7
- DRSNWIFPQOZJSZ-UHFFFAOYSA-N [1,3]thiazolo[5,4-c]isoquinolin-2-amine Chemical group NC=1SC=2N=CC=3C=CC=CC3C2N1 DRSNWIFPQOZJSZ-UHFFFAOYSA-N 0.000 claims description 3
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 claims description 3
- ZLPCNNLXLMZZIV-UHFFFAOYSA-N 1H-[1,3]thiazolo[5,4-c]isoquinolin-2-one Chemical group OC=1SC=2N=CC=3C=CC=CC3C2N1 ZLPCNNLXLMZZIV-UHFFFAOYSA-N 0.000 claims description 2
- BQDAOGQCQKHECU-UHFFFAOYSA-N 2-chloro-[1,3]thiazolo[5,4-c]isoquinoline Chemical group ClC=1SC=2N=CC=3C=CC=CC3C2N1 BQDAOGQCQKHECU-UHFFFAOYSA-N 0.000 claims description 2
- NQZQACUKSKXWMB-UHFFFAOYSA-N 3H-[1,3]thiazolo[4,5-c]isoquinolin-2-one Chemical compound O=c1[nH]c2ncc3ccccc3c2s1 NQZQACUKSKXWMB-UHFFFAOYSA-N 0.000 claims 1
- SZDAVVJBBHIZHV-UHFFFAOYSA-N ClC=1SC2=C(N=CC=3C=CC=CC2=3)N=1 Chemical compound ClC=1SC2=C(N=CC=3C=CC=CC2=3)N=1 SZDAVVJBBHIZHV-UHFFFAOYSA-N 0.000 claims 1
- CEWCKUSQGANLCP-UHFFFAOYSA-N [1,3]thiazolo[4,5-c]isoquinoline Chemical compound C1=CC=CC2=C(SC=N3)C3=NC=C21 CEWCKUSQGANLCP-UHFFFAOYSA-N 0.000 abstract description 3
- 230000035945 sensitivity Effects 0.000 description 8
- 108010010803 Gelatin Proteins 0.000 description 5
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- 238000011161 development Methods 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 150000002537 isoquinolines Chemical class 0.000 description 5
- 150000003573 thiols Chemical class 0.000 description 5
- 239000000975 dye Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001475 halogen functional group Chemical group 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 230000001235 sensitizing effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- FVVXWRGARUACNW-UHFFFAOYSA-N 3-methylisoquinoline Chemical compound C1=CC=C2C=NC(C)=CC2=C1 FVVXWRGARUACNW-UHFFFAOYSA-N 0.000 description 2
- WZDWCCKTXKIWTN-UHFFFAOYSA-N [1,3]thiazolo[5,4-c]isoquinoline Chemical compound C1=CC=C2C(N=CS3)=C3N=CC2=C1 WZDWCCKTXKIWTN-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000007888 film coating Substances 0.000 description 2
- 238000009501 film coating Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 239000004848 polyfunctional curative Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- LUMLZKVIXLWTCI-NSCUHMNNSA-N (e)-2,3-dichloro-4-oxobut-2-enoic acid Chemical compound OC(=O)C(\Cl)=C(/Cl)C=O LUMLZKVIXLWTCI-NSCUHMNNSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 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
- SOFPIAMTOZWXKT-UHFFFAOYSA-N 2h-1,2,4-triazine-3-thione Chemical class SC1=NC=CN=N1 SOFPIAMTOZWXKT-UHFFFAOYSA-N 0.000 description 1
- DTBDAFLSBDGPEA-UHFFFAOYSA-N 3-Methylquinoline Natural products C1=CC=CC2=CC(C)=CN=C21 DTBDAFLSBDGPEA-UHFFFAOYSA-N 0.000 description 1
- 208000032484 Accidental exposure to product Diseases 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 241000779745 Backhousia myrtifolia Species 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 229910021612 Silver iodide Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FJWGYAHXMCUOOM-QHOUIDNNSA-N [(2s,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6s)-4,5-dinitrooxy-2-(nitrooxymethyl)-6-[(2r,3r,4s,5r,6s)-4,5,6-trinitrooxy-2-(nitrooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-3,5-dinitrooxy-6-(nitrooxymethyl)oxan-4-yl] nitrate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O)O[C@H]1[C@@H]([C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@@H](CO[N+]([O-])=O)O1)O[N+]([O-])=O)CO[N+](=O)[O-])[C@@H]1[C@@H](CO[N+]([O-])=O)O[C@@H](O[N+]([O-])=O)[C@H](O[N+]([O-])=O)[C@H]1O[N+]([O-])=O FJWGYAHXMCUOOM-QHOUIDNNSA-N 0.000 description 1
- HOLVRJRSWZOAJU-UHFFFAOYSA-N [Ag].ICl Chemical compound [Ag].ICl HOLVRJRSWZOAJU-UHFFFAOYSA-N 0.000 description 1
- 231100000818 accidental exposure Toxicity 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 150000001541 aziridines Chemical class 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229920002301 cellulose acetate Polymers 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
- 229920001577 copolymer Polymers 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000000586 desensitisation Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- YGZZDQOCTFVBFC-UHFFFAOYSA-L disodium;1,5-dihydroxypentane-1,5-disulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C(O)CCCC(O)S([O-])(=O)=O YGZZDQOCTFVBFC-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- JGEMYUOFGVHXKV-OWOJBTEDSA-N fumaraldehyde Chemical compound O=C\C=C\C=O JGEMYUOFGVHXKV-OWOJBTEDSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical class [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- CBEQRNSPHCCXSH-UHFFFAOYSA-N iodine monobromide Chemical compound IBr CBEQRNSPHCCXSH-UHFFFAOYSA-N 0.000 description 1
- 230000007775 late Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- ZAKLKBFCSHJIRI-UHFFFAOYSA-N mucochloric acid Natural products OC1OC(=O)C(Cl)=C1Cl ZAKLKBFCSHJIRI-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000008427 organic disulfides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-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
- 230000003595 spectral effect Effects 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920003176 water-insoluble polymer Polymers 0.000 description 1
- 239000002023 wood 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
- G03C1/06—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
- G03C1/346—Organic derivatives of bivalent sulfur, selenium or tellurium
Definitions
- This invention relates to photography.
- this invention relates to the stabilization of photographic silver halide elements and emulsions against spontaneous fog without adversely affecting the photographic sensitivity of said silver halide elements and emulsion.
- Fog depends upon both the particular emulsion and the conditions of development. For a given emulsion fog increases with the degree of development. At constant development conditions fog generally increases with the temperature, time and relative humidity of storage conditions.
- the isoquinolines which have been found useful can be a thiazolo[5,4-clisoquinoline, a thiazolo[4,5-c]isoquinoline, a 2-halo, hydroxy, thiol or aminothiazolo[5,4-clisoquinoline or a 2-halo, hydroxy, thiol or amino[4,5-clisoquinoline.
- each R can be hydrogen, halide, hydroxy, thiol or amino.
- isoquinoline portion of the compounds of this invention can be substituted with any radical, such as alkyl radicals, aryl radicals, and the like, as long as such substitutions do not destroy the antifoggant properties of the compound.
- examples of the isoquinolines are:
- the concentration of the stabilizing compounds can vary considerably depending on various factors such as the effects desired, silver content of the photographic elements, the nature of the particular silver halide, the degree of ripening, the location of the stabilizer in relation to the silver halide, the particular stabilizer, etc. In general, a concentration in the range of about 0.00] grams to about 10 grams of stabilizer per mole of silver halide is useful. A preferred range is from about 0.03 grams to about 0.5 grams of stabilizer per mole of silver halide. In accordance with the invention, one may use the higher concentrations without inducing a reduction in sensitivity. The optimum concentration of stabilizer for a particular photographic system can be determined through techniques well known in the art.
- the stabilizing addenda can be added in a variety of ways and at various stages in the preparation of the photographic system.
- the stabilizers can be incorporated directly into silver halide elements and emulsion, preferably before the final digestion operation in the case of emulsions and after the silver halide grains are substantially in their final size and shape.
- the addenda can be added to a layer adjacent to the silver halide layer.
- the solvents in which the stabilizers may be dissolved are restricted to those that are not harmful to the silver halide emulsion, and in accordance with the general practice organic solvents and diluents are preferred.
- the light-sensitive silver halide emulsions comprising the antifoggants of this invention can contain addenda such as gelatin plasticizers, coating aids and hardeners such as the aldehyde-type hardeners, e.g., formaldehyde, mucochloric acid, glutaraldehyde bis(sodium bisulfite), maleic dialdehyde, and aziridines, dioxane derivatives, vinylsulfonylethers and oxypolysaccharides.
- Sensitizing dyes useful in sensitizing such emulsions are described, for example, in U.S. Pat. Nos. 2,526,632 of Brooker and White issued Oct. 24, 1950, and 2,503,776 of Sprague issued Apr. 11, 1950.
- Spectral sensitizers which can be used are the cyanines, merocyanines,
- Developing agents can also be incorporated into the emulsion if desired or can be contained in a separate underlayer.
- Supports such as paper that are coated with alpha-olefin polymers, particularly polymers of alpha-olefins containing two or more carbon atoms, as for example, polyethylene, polypropylene, ethylene-butene copolymers and the like, can
- the stabilizing addenda employed in the practice of this in also be employed.
- vention can be used in various kinds of photographic emul- Photographic layers comprising the antifoggants can also sions. in addition to being useful in orthochromatic, panchron in Speed-increasing compounds such as quaternary ammatic and infrared emulsions, they are also useful in X-ray and monium compounds, polyethylene glycols or thioethers. other nonspectrally sensitized emulsions. They can be added eq y.
- Varigraphic y ous silver salts can be used as sensitive salts, including for ex- Silver halide emulsions containing the flmifoggants 0f the ample, silver bromide, silver iodide, silver chloride, silver instant invention can be sensitized using of the chlorobromide, silver bromoiodide, or silver chloroiodide and l f twhm'ilues emulsion f" p y 3 the like.
- the silver halides can be those which form latent mg with naturally active gelatin or Vanous 'v selem'um images predominantly on the surface of the silver halide grains tellul'lum Compounds and/0r gold compounds-
- the emulsions or those hi f knem images inside the Silver halide can also be sensitized with salts of noble metals of Group VIII erystalssueh as described in US. Pat. No. 2,592,250 of Davey of the Periodic Table which have an atomic weight greater and Knott issued Apr. 8, 1952.
- the subject addenda can be I used in emulsions intended for color photography, for examsllver hahde emulslolls f l the anufoggams of h pie, emulsions containing color forming couplers or emulsions l 2 can be used "l T Processes wh'ch m be developed by solutions Containing couphrs or other utilize the undeveloped silver halide in nonimage areas of the color-generating materials, emulsions of the mixed-packet- 2 F form a R w?
- the h ⁇ also be F l" d'ffuslon transfer for preparing silver halide emulsions there can be employed as F P wlllch a dlffuslon transfer of an the dispersing agent, orubindersw as they are known in the an.
- the binding agents for the EXAMPLES emulsion layer of the photographic element can also contain 40 dispersed polymerized vinyl compounds.
- Such compounds are Compounds employed in this invention, listed in the table disclosed, for example, in US. Pat. Nos. 3,142,568 of Nottorf below, are incorporated, at concentrations listed in the table, issued July 28, 1964; 3,193,386 of White issued July 6, 1965; into separate samples of a high-speed gelatino silver 3,062,674 of Houck, Smith and Yudelson, issued Nov. 30, bromoiodide photographic emulsion.
- Each of the emulsions 1965' and include the water-insoluble polymers of alkyl acryare coated on a cellulose acetate film support at a coverage of lates and methacrylates, acrylic acid, sulfoalkyl acrylates or 459 mg.
- A 2-aminothiazolo[5,4-c lsoqulnoline.
- a photographic silver halide emulsion comprising a stacompounds of this invention are highly useful as stabilizers bilizing compound selected from the general formulas; and fog inhibitors for photographic silver halides. It should be noted that fog is inhibited without any concurrent substantial "R Sfi-dt loss, if any, in the photographic sensitivity of the silver halide I N emulsion. In the case of the incubated samples the speed of the treated emulsions is always greater than the nontreated 6 samples. With respect to the fresh samples there was an insig- N nificant loss in speed, if any.
- the invention provides silver halide emulsions and 10 elements stabilized with the particular antifoggants said anwh i h R i h d h lid h d thin] or in tifoggants not causing any substantial deleterious effect upon id t bili i compound i present i a n ntration f speed or sensitivity. from about 0.001 to about l0.0 g.
- a photographic element comprising a support, a silver halide layer and as a stabilizer a thiazolo[5,4-c]isoquinoline, a thiazolo[4,5-cisoquinoline, a 2-halo, hydroxy, thiol or aminothiazolo[5,4-c]isoquinoline or a 2-halo, hydroxy, thiol or aminothiazolo[4,5-c]isoquinoline.
- a photographic element comprising a support, a silver halide layer and as a stabilizer a compound having the formula selected from the group consisting of 6.
- a photographic emulsion as in claim 4 wherein said stabilizer is 2-chlorothiazolo[5,4-c]isoquinoline or 2- chlorothiazolo[4,5-clisoquinoline.
- each R is hydrogen, halide hydroxy hiolwor aminol l.
- a method for stabilizing photographic silver halide A photographic element as in claim 2 wherein said Stabn againstfog which comprises contacting said silver halide with izer is present in a concentration of from about 0001 to astabilizmg compound havlngaformula according to claim 1.
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- 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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86488769A | 1969-10-08 | 1969-10-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3630745A true US3630745A (en) | 1971-12-28 |
Family
ID=25344291
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US864887A Expired - Lifetime US3630745A (en) | 1969-10-08 | 1969-10-08 | THIAZOLO {8 5,4-c{9 ISOQUINOLINE AND THIAZOLO {8 4,5-c{9 IOSQUINOLINE AND DERIVATIVES AS ANTIFOGGANTS FOR PHOTOGRAPHIC LAYERS |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3630745A (fr) |
| BE (1) | BE757258A (fr) |
| CA (1) | CA921751A (fr) |
| FR (1) | FR2065104A5 (fr) |
| GB (1) | GB1319267A (fr) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4082553A (en) * | 1975-04-10 | 1978-04-04 | Eastman Kodak Company | Interimage effects with spontaneously developable silver halide |
| US4113731A (en) * | 1975-08-27 | 1978-09-12 | Gruppo Lepetit S.P.A. | Fused isoquinoline derivatives |
| US4232017A (en) * | 1978-05-26 | 1980-11-04 | Gruppo Lepetit S.P.A. | Treatment of psychic disorders and inflammation with fused isoquinolines |
| JP2025533951A (ja) * | 2022-10-28 | 2025-10-09 | 杭州聖域生物医薬科技有限公司 | 縮合環含窒素化合物、その中間体、調製方法および用途 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2948615A (en) * | 1958-03-13 | 1960-08-09 | Gen Aniline & Film Corp | Antifoggants and stabilizers for photographic silver halide emulsions |
| US3046130A (en) * | 1960-05-12 | 1962-07-24 | Gen Aniline & Film Corp | Photographic materials containing a chemical sensitizer |
| US3084044A (en) * | 1960-12-09 | 1963-04-02 | Gen Aniline & Film Corp | Nitrogenous heterocyclic carboxyal-kylmercapto polyoxyalkylene ester photographic sensitizer |
| US3271154A (en) * | 1961-11-30 | 1966-09-06 | Gen Aniline & Film Corp | Antifogging and stabilizing agents for photography |
| US3418131A (en) * | 1966-02-01 | 1968-12-24 | Du Pont | Method of stabilizing the background in light developable silver halide emulsions using thiazole containing compounds |
-
0
- BE BE757258D patent/BE757258A/fr unknown
-
1969
- 1969-10-08 US US864887A patent/US3630745A/en not_active Expired - Lifetime
-
1970
- 1970-09-09 CA CA092655A patent/CA921751A/en not_active Expired
- 1970-10-07 FR FR7036148A patent/FR2065104A5/fr not_active Expired
- 1970-10-08 GB GB4791670A patent/GB1319267A/en not_active Expired
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2948615A (en) * | 1958-03-13 | 1960-08-09 | Gen Aniline & Film Corp | Antifoggants and stabilizers for photographic silver halide emulsions |
| US3046130A (en) * | 1960-05-12 | 1962-07-24 | Gen Aniline & Film Corp | Photographic materials containing a chemical sensitizer |
| US3084044A (en) * | 1960-12-09 | 1963-04-02 | Gen Aniline & Film Corp | Nitrogenous heterocyclic carboxyal-kylmercapto polyoxyalkylene ester photographic sensitizer |
| US3271154A (en) * | 1961-11-30 | 1966-09-06 | Gen Aniline & Film Corp | Antifogging and stabilizing agents for photography |
| US3418131A (en) * | 1966-02-01 | 1968-12-24 | Du Pont | Method of stabilizing the background in light developable silver halide emulsions using thiazole containing compounds |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4082553A (en) * | 1975-04-10 | 1978-04-04 | Eastman Kodak Company | Interimage effects with spontaneously developable silver halide |
| US4113731A (en) * | 1975-08-27 | 1978-09-12 | Gruppo Lepetit S.P.A. | Fused isoquinoline derivatives |
| US4232017A (en) * | 1978-05-26 | 1980-11-04 | Gruppo Lepetit S.P.A. | Treatment of psychic disorders and inflammation with fused isoquinolines |
| JP2025533951A (ja) * | 2022-10-28 | 2025-10-09 | 杭州聖域生物医薬科技有限公司 | 縮合環含窒素化合物、その中間体、調製方法および用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| BE757258A (fr) | 1971-03-16 |
| GB1319267A (en) | 1973-06-06 |
| CA921751A (en) | 1973-02-27 |
| FR2065104A5 (fr) | 1971-07-23 |
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