US3770440A - Spectrally sensitized photographic silver halide emulsion - Google Patents
Spectrally sensitized photographic silver halide emulsion Download PDFInfo
- Publication number
- US3770440A US3770440A US00149276A US3770440DA US3770440A US 3770440 A US3770440 A US 3770440A US 00149276 A US00149276 A US 00149276A US 3770440D A US3770440D A US 3770440DA US 3770440 A US3770440 A US 3770440A
- Authority
- US
- United States
- Prior art keywords
- silver halide
- group
- halide emulsion
- emulsion
- photographic silver
- 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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- 239000000839 emulsion Substances 0.000 title claims abstract description 39
- -1 silver halide Chemical class 0.000 title claims abstract description 33
- 229910052709 silver Inorganic materials 0.000 title claims abstract description 25
- 239000004332 silver Substances 0.000 title claims abstract description 25
- 230000001235 sensitizing effect Effects 0.000 claims abstract description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical group [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 2
- 229940077388 benzenesulfonate Drugs 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Chemical group SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical group OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical group CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 claims 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical group COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 150000001450 anions Chemical class 0.000 abstract description 3
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 3
- 125000000547 substituted alkyl group Chemical group 0.000 abstract description 3
- 125000004964 sulfoalkyl group Chemical group 0.000 abstract description 2
- 239000000975 dye Substances 0.000 description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 230000035945 sensitivity Effects 0.000 description 10
- 230000003595 spectral effect Effects 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229960001413 acetanilide Drugs 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- ZVNPWFOVUDMGRP-UHFFFAOYSA-N 4-methylaminophenol sulfate Chemical compound OS(O)(=O)=O.CNC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1 ZVNPWFOVUDMGRP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010070834 Sensitisation Diseases 0.000 description 2
- 235000010724 Wisteria floribunda Nutrition 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000005242 carbamoyl alkyl group Chemical group 0.000 description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 description 2
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 230000008313 sensitization Effects 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 2
- AIGNCQCMONAWOL-UHFFFAOYSA-N 1,3-benzoselenazole Chemical compound C1=CC=C2[se]C=NC2=C1 AIGNCQCMONAWOL-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- MPVVLNVZVJCCOQ-UHFFFAOYSA-M 5,6-dichloro-1,3-diethyl-2-methylbenzimidazol-3-ium;iodide Chemical compound [I-].ClC1=C(Cl)C=C2N(CC)C(C)=[N+](CC)C2=C1 MPVVLNVZVJCCOQ-UHFFFAOYSA-M 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 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
- 241000981595 Zoysia japonica Species 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 1
- XCFIVNQHHFZRNR-UHFFFAOYSA-N [Ag].Cl[IH]Br Chemical compound [Ag].Cl[IH]Br XCFIVNQHHFZRNR-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 229910001864 baryta Inorganic materials 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000006081 fluorescent whitening agent Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000003897 fog Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/16—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms
- C09B23/162—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms only nitrogen atoms
- C09B23/164—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms only nitrogen atoms containing one nitrogen atom
-
- 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
- G03C1/12—Methine and polymethine dyes
Definitions
- Z represents an atomic group necessary to complete a benzene ring, the hydrogen atom'of which may be substituted; R and R -each represent a member 6 Claims, 1 Drawing Figure PATENTEDNUV 6 I975 B F F U I 8 E I D /DYE STUFF l0 WAVELENGTH (my) INVENTORS AKIRA SATO KEISUKE SHIBA MASANAO HINATA Q axnq Tiffani? 0m,
- the above mentioned object of the invention can be accomplished by incorporating a new sensitizing dye represented by the following general formula (I) or (II) in a silver halide emulsion.
- Z represents an atomic group necessary for forming a benzene ring, the hydrogen atom of which may be substituted for by conventional substituents for benzimidazolo cyanine dyes.
- substituents in this case are those well known for benzimidazolocarbocyanines, such as halogen atoms, e.g.
- R and R represent the same or different alkyl groups, such as methyl, ethyl, n-propyl and n-butyl groups, and substituted alkyl groups conventionally used as nitrogen substituents in benzimidazolo cyanine dyes, except a sulfoalkyl group, such as hydroxy alkyl (e.g. B-hydroxyethyl, -y-hydroxypropyl), acetoxyalkyl (e.g. B-acetoxyethyl, 'y-acetoxypropyl) carboxyalkyl (e.g.
- hydroxy alkyl e.g. B-hydroxyethyl, -y-hydroxypropyl
- acetoxyalkyl e.g. B-acetoxyethyl, 'y-acetoxypropyl
- carboxyalkyl e.g.
- fl-carbamoylethyl 'y-carbamoyl-propyl, B-carbamoylbutyl, fl-N-ethylcarbamoylethyb, y-N-ethylcarbamoylpropyl, B-N-methylcarbarnoylbutyl), sulfamoylalkyl (e.g. 'y-sulfamoylpropyl, 8-sulfamoylbutyl), aminosulfonylalkyl (e.g.
- A represents aryl groups, such as a phenyl group, a methoxyphenyl, a tolyl or a chlorophenyl group.
- X represents an acid anion, such as a chloride, bromide, iodide, thiocyanate, perchlorate, benzenesulfonate, p-toluene-sulfonate, niethylsulfate or ethylsulfate ion.
- the feature of the sensitizing dyes of this invention resides in the fact that they are limited by general formulas (I) or (II) to a tetramethinehemicyanine or tetramethinehemicyanine base having a benzimidazole nucleus which tends to form a .l-aggregate.
- these dyes are effective for raising the spectral sensitivity in the orthoregion.
- tetramethinehemicyanines or tetramethinehemicyanine bases having benzothiazole, benzoselenazole or benzoxazole nucleus mentioned in U.S. Pat. Nos. 2,369,509 and 2,369,509 are difficult to form the J-aggregate and have a low spectral sensitivity.
- the sensitizing dyes represented by general formula (II) are obtainable by treating the sensitizing dye (I) with an aqueous akaline solution and removing the I-IX.
- the acetanilide intermediate is dissolved in methanol and then mixed with 4N caustic soda and with water to deposit a crystal which is then filtered, washed with water and recrystallized from methanol to obtain 1.5 g of Dye 3melting at 274C.
- the sensitizing dyes used in this invention are capable of spectrally sensitizing a silver halide photographic emulsion, and in particular, effectively enlarging the light-sensitive region of a gelatino-silver halide photographic emulsion. They can also sensitize other photographic emulsions containing a hydrophilic colloid besides gelatin. Illustrative of these are agar colloidion, cellulose derivatives, polyvinyl alcohol or a natural hydrophilic resin.
- various silver salts such as mixed silver halides, such a s silver iodobromide, silver chlorobromide, a silver chloroiodobromide, and silver bromide.
- the sensitizing dye may be added to a photographic emulsion in a conventional manner.
- the sensitizing dye is dissolved in a suitable solvent, such as methanol and added to an emulsion in the form of a solution.
- a suitable solvent such as methanol
- the quantity of the sensitizing dye to be incorporated in the emulsion may be varied within a wide range of 5-200 mg per 1 kg of the emulsion according to the desired effect.
- sensitizing dyes as well as commonly used additives, such as sensitizers, stabilizers, color tone regulators, hardeners, surfactants, fog inhibitors, plasticizers, development accelerators, color couplers, fluorescent whitening agents and ultraviolet ray absorbers.
- the photographic emulsion of this invention may be coated in a conventional manner onto a suitable support member, such as glass, a cellulose derivative film, a synthetic resin film, baryta paper, a resin laminated paper or synthetic paper.
- a suitable support member such as glass, a cellulose derivative film, a synthetic resin film, baryta paper, a resin laminated paper or synthetic paper.
- a photographic silver halide emulsion was prepared by adding the following sensitizing dye of this invention to a gelatino-silver iodobromide emulsion (AgI AgBr 6 mols 94 mols) or gelatino-silver chlorobromide emulsion (AgBr AgCl 40 mols 60 mols).
- This emulsion was coated onto a cellulose triacetate film base, dried, exposed to a light source of daylight color of 64 luxes (corresponding to 5,400K) through a Fuji No. 3 Filter (yellow filter) and then developed.
- the spectral sensitivity is a specific sensitivity when the spectral sensitivity of the sensitizing dye B is 100 when exposed using a Fuji No. 3 Filter (yellow filter).
- the chemical structural formulas of the sensitizing dyes used for the comparison are as follows:
- FIG. 1 shows spectrograms of the sensitizing dye 10, a typical example of the new sensitizing dyes according to this invention, (solid line) and the dye B for comparison (broken line) It will be understood from the drawing that the sensitizing dye of this invention forms a J-aggregate. This is a very excellent attribute as disclosed earlier.
- Z represents an atomic group necessary to complete a benzene ring, which may be substituted or unsubstituted, said substituents being selected from the group consisting of halogen, trifluoromethyl, trifluoromethylsulfonyl, alkylsulfonyl, sulfamoyl, al-
- R and R each represents a member selected from the group consisting of the same or a different alkyl group and a substituted alkyl group selected from the group consisting of hydroxyalkyl, acetoxyalkyl, carboxyalkyl, cyanoalkyl, carbamoylalkyl, sulfamoylalkyl, aminosulfonylalkyl, allyl and aralkyl;
- A represents an aryl group, and X represents an acid anion.
- the photographic silver halide emulsion of claim 1 wherein the sensitizing dye is selected from the group consisting of Dye 1 Calls l CHzCHzCI-Iz UN 5.
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- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP45047381A JPS4912655B1 (enrdf_load_stackoverflow) | 1970-06-02 | 1970-06-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3770440A true US3770440A (en) | 1973-11-06 |
Family
ID=12773505
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00149276A Expired - Lifetime US3770440A (en) | 1970-06-02 | 1971-06-02 | Spectrally sensitized photographic silver halide emulsion |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3770440A (enrdf_load_stackoverflow) |
| JP (1) | JPS4912655B1 (enrdf_load_stackoverflow) |
| BE (1) | BE767983A (enrdf_load_stackoverflow) |
| DE (1) | DE2127347C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2109604A5 (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT2816U3 (de) * | 1998-11-19 | 1999-08-25 | Balloonart Veranstaltungs Gmbh | Werbeträger mit einer aufblasbaren hülle und mit einem drucklufterzeuger |
| EP1750173A1 (en) | 2005-08-04 | 2007-02-07 | Fuji Photo Film Co., Ltd. | Silver halide photosensitive material and packaged body containing the same |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2298732A (en) * | 1940-12-16 | 1942-10-13 | Eastman Kodak Co | Polymethine base |
| US2369509A (en) * | 1940-12-04 | 1945-02-13 | Eastman Kodak Co | Polymethine compounds and process for preparing them |
| US2553989A (en) * | 1947-03-14 | 1951-05-22 | Gevaert Photo Prod Nv | Hemicyanine dyestuffs |
| US3490910A (en) * | 1968-02-02 | 1970-01-20 | Gaf Corp | Silver halide emulsions sensitized with cyanine dyes containing a tetrahydrobenzo-benzoxazole nucleus |
-
1970
- 1970-06-02 JP JP45047381A patent/JPS4912655B1/ja active Pending
-
1971
- 1971-06-02 BE BE767983A patent/BE767983A/xx unknown
- 1971-06-02 DE DE2127347A patent/DE2127347C3/de not_active Expired
- 1971-06-02 US US00149276A patent/US3770440A/en not_active Expired - Lifetime
- 1971-06-02 FR FR7119939A patent/FR2109604A5/fr not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2369509A (en) * | 1940-12-04 | 1945-02-13 | Eastman Kodak Co | Polymethine compounds and process for preparing them |
| US2298732A (en) * | 1940-12-16 | 1942-10-13 | Eastman Kodak Co | Polymethine base |
| US2553989A (en) * | 1947-03-14 | 1951-05-22 | Gevaert Photo Prod Nv | Hemicyanine dyestuffs |
| US3490910A (en) * | 1968-02-02 | 1970-01-20 | Gaf Corp | Silver halide emulsions sensitized with cyanine dyes containing a tetrahydrobenzo-benzoxazole nucleus |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT2816U3 (de) * | 1998-11-19 | 1999-08-25 | Balloonart Veranstaltungs Gmbh | Werbeträger mit einer aufblasbaren hülle und mit einem drucklufterzeuger |
| EP1750173A1 (en) | 2005-08-04 | 2007-02-07 | Fuji Photo Film Co., Ltd. | Silver halide photosensitive material and packaged body containing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2127347A1 (de) | 1971-12-16 |
| DE2127347B2 (de) | 1973-08-09 |
| BE767983A (fr) | 1971-11-03 |
| FR2109604A5 (enrdf_load_stackoverflow) | 1972-05-26 |
| DE2127347C3 (de) | 1974-03-14 |
| JPS4912655B1 (enrdf_load_stackoverflow) | 1974-03-26 |
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