US2298731A - Pyrrole filter and backing dye - Google Patents
Pyrrole filter and backing dye Download PDFInfo
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- US2298731A US2298731A US317726A US31772640A US2298731A US 2298731 A US2298731 A US 2298731A US 317726 A US317726 A US 317726A US 31772640 A US31772640 A US 31772640A US 2298731 A US2298731 A US 2298731A
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- pyrrole
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- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 50
- 239000000975 dye Substances 0.000 description 41
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 39
- 239000013078 crystal Substances 0.000 description 35
- 239000000839 emulsion Substances 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- 238000002844 melting Methods 0.000 description 22
- 230000008018 melting Effects 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 238000000354 decomposition reaction Methods 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- 238000001953 recrystallisation Methods 0.000 description 21
- 239000000126 substance Substances 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 238000012216 screening Methods 0.000 description 11
- 238000009835 boiling Methods 0.000 description 7
- 150000003233 pyrroles Chemical class 0.000 description 7
- 229910052709 silver Inorganic materials 0.000 description 7
- 239000004332 silver Substances 0.000 description 7
- -1 silver halide Chemical class 0.000 description 7
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 230000035945 sensitivity Effects 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 230000011514 reflex Effects 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 229930003836 cresol Natural products 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- JMCYJDYOEWQZDE-UHFFFAOYSA-N 2-phenylindolizine Chemical compound C=1N2C=CC=CC2=CC=1C1=CC=CC=C1 JMCYJDYOEWQZDE-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 150000002475 indoles Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZJXMRHDTQFPICU-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2,5-dimethylpyrrole Chemical compound C1=CC(OC)=CC=C1N1C(C)=CC=C1C ZJXMRHDTQFPICU-UHFFFAOYSA-N 0.000 description 1
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 1
- GAMQVQVHTKTWCA-UHFFFAOYSA-N 1-dodecyl-2,5-dimethylpyrrole Chemical compound CCCCCCCCCCCCN1C(C)=CC=C1C GAMQVQVHTKTWCA-UHFFFAOYSA-N 0.000 description 1
- UDAZJESCCMCDKC-UHFFFAOYSA-N 1-dodecyl-2,5-dimethylpyrrole-3-carbaldehyde Chemical compound C(CCCCCCCCCCC)N1C(=C(C=C1C)C=O)C UDAZJESCCMCDKC-UHFFFAOYSA-N 0.000 description 1
- OUYLXVQKVBXUGW-UHFFFAOYSA-N 2,3-dimethyl-1h-pyrrole Chemical compound CC=1C=CNC=1C OUYLXVQKVBXUGW-UHFFFAOYSA-N 0.000 description 1
- SLRBXAUDEQGJCB-UHFFFAOYSA-N 2,5-dimethyl-1-octadecylpyrrole Chemical compound CCCCCCCCCCCCCCCCCCN1C(C)=CC=C1C SLRBXAUDEQGJCB-UHFFFAOYSA-N 0.000 description 1
- HDZQTFWZGOUZIP-UHFFFAOYSA-N 2-(furan-2-ylmethyl)-1h-pyrrole Chemical compound C=1C=COC=1CC1=CC=CN1 HDZQTFWZGOUZIP-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 1
- DQSHFKPKFISSNM-UHFFFAOYSA-N 2-methylbenzoxazole Chemical compound C1=CC=C2OC(C)=NC2=C1 DQSHFKPKFISSNM-UHFFFAOYSA-N 0.000 description 1
- HRUAZBSVPMQJJL-UHFFFAOYSA-N 2-methylindolizine Chemical compound C1=CC=CN2C=C(C)C=C21 HRUAZBSVPMQJJL-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229910000906 Bronze Inorganic materials 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 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
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000010974 bronze Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- PWPXSQUXDZUGJW-UHFFFAOYSA-N ethyl 4-formyl-2,5-dimethyl-1h-pyrrole-3-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C1C=O PWPXSQUXDZUGJW-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical compound O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 description 1
- 239000012260 resinous material Substances 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
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Images
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
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
- G03C1/83—Organic dyestuffs therefor
-
- 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
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
- G03C1/83—Organic dyestuffs therefor
- G03C1/832—Methine or polymethine dyes
Definitions
- This invention relates to improvements in photographic elements and more particularly in photographic elements having light screening substances therein.
- screening substance may be in a layer overlying a light sensitive emulsion or overlying two or more light sensitive emulsions; or it may be in a light sensitive emulsion for the purpose of modifying a light record in such emulsion or of protecting an underlying light sensitive emulsion or emulsions from the action of light of wave length absorbed by such light screening substance; or it may be in a layer not containing a light sensitive substance but arranged between two light sensitive emulsions; or it may be in a layer serving as a backing on an element having one or more light sensitive emulsions (for example, to reduce halation.)
- light screening substances are often required (a) in overcoatings upon photographic elements to protect the light sensitive emulsion or emulsions from the action of light which it is not desired to record, e. g. ultra-violet light in the case of still or moving pictures, especially color pictures, (b) in layers arranged between differentially color-sensitized emulsions, e. g. to protect redand green-sensitized emulsions from the action of blue light and (c) in backings, forming the so-called anti-halation layers, on either-side of a transparent support carrying the light-sensitive emulsion or emulsions.
- a transparent support carrying the light-sensitive emulsion or emulsions.
- decolorised Such a light or destroyed and removed, prior to or during or after photographic processing; for many purposes it is particularly convenient to employ lightscreening substances which are rendered ineffective by one of the photographic baths employed in processing the element after exposure, e. g. a photographic developing bath or fixing bath or a silver-oxidizing (including silver-removing) bath.
- a photographic developing bath or fixing bath or a silver-oxidizing (including silver-removing) bath e.g. a photographic developing bath or fixing bath or a silver-oxidizing (including silver-removing) bath.
- a silver-oxidizing (including silver-removing) bath e.g., silver-oxidizing (including silver-removing) bath.
- a light screening substance which is rendered ineffective by the developer employed to develop the latent image or images to silver since exposure to light of the residual light sensitive emulsion or emulsions may thereby be facilitated.
- differentially colorsensitized emulsions constituted, for example, by silver halide, such as silver bromide dispersed in gelatin, collodion or other colloid, are coated on one or both sides of a support, for example in inseparably-superimposed layers.
- difierentially color-sensitized emulsions have to be processed to difierent colors and to facilitate the differential color-processing, methods involving selective exposure of light sensitive images in the layers may be employed.
- selective re-exposure e. g.
- any of the elements referred to above may be such that one or more of the emulsions contain coupling components, e. g. those described in French Patent 834,37l, granted August 16, 1938.
- This class consists of polymethine dyes-derived from pyrrole orindole or from their substituted derivatives.
- Such dyes may have a pyrrole nucleus or an indole nucleus (in either case containing substituents or not) linked to a heterocycllc nucleus containing a nitrogen atom either directly ,or
- Example 6 Hn 3[(3-ethyl-2(3)-benzothiazoiyiidenei ethyiidene]-2 methyiindolenine hydro-iodide 2.25 g. (1 mol.) 2-p-acetaniiidovinylbenzothlazoie ethiodide, 2.6 g. (1 moi.+100%) a-methyir indole and cc. of acetic anhydride were refluxed 5 minutes. The orange solution was chilled, filtered, the dye washed with acetone and water and dried. Yield 1.8 g., 81%.
- Example 10 (3-ethyl-2-benzoxazole)-(2,5'dimethyi-l-phenyl-Ztpyrrole) dimethinecyaniue iodide 4.35 g., (1 mol.) Z-fl-acetaniiidovinylbenzoxazole ethiodide, 6.0 g. (l mol.+300%) 2,5-dimethylrl-phenylpyrrole and 25 cc. acetic anhydride were refluxed 15 minutes. The orange mixture was chilled, filtered, product washed with water and acetone and dried. Brown crystals. Yield 2.7 g. 57%.
- Example 12 4.34 g. (1 mol.) 2-p-acetanilidovinylbenzoxazole ethiodide, 4.0 g. (1 mol.+100%) 2,5-dimethyl-1- p-methoxy-phenylpyrrole and 15 cc. acetic anhydride were refluxed 15 minutes. Orange coloration. Chilled, filtered, washed with acetone and water and dried. Brown crystals. Yield 2.5 g.,
- Example 13 Me NJMe I (eetyl and octadecyl mixture) ethinecyanine iodide 4.34 g. (1 mol.) 2-fi-acetanilidovinylbenzoxazolek ethiodide, 6.4 g. (1 mol.+100%) mixture of'lcetyl-2,5-dimethylpyrrole and 1-octadecyl-2,5-dimethylpyrrole and 20 cc. acetic anhydride were refluxed minutes. Chilled, filtered, washed with acetone and water and dried. Brown crystals. Yield 4.1 g., 66%. After recrystallization from abs. EtOH (5 cc./g.)" the product was obtained as brown needles melting with decomposition at 180-183. yellow.
- Example 14 N(Me) 1- di th 1 f 2.ii.35%;?lldfidligilliiii. "4.34 g. (1 mol.) 2-p-acetanilidovinylbenzoxazole ethiodide, 4.3 g. (1 mol. 100%) 1-p-dimethylaminophenyl-2,5-dimethyl pyrrole and Yield 3.7 g., 60%. MeOH solution p-hydroxyethobromide, 5 drops piperidine and 15 '25 lution yellow.
- Example 17 I (3-ethyl-2-benzoxazole)-(2-methyl-l-pyrroooline) dimethinecyaniue iodide O 4.34 g. (1 mol.) 2-p-acetanilidoyinylbenzoxazole ,ethiodide, 1.3 g. (1 mol.) 2-methylpyrrocoline and 15 cc. glacial acetic acid were refluxed 5 minutes. Red coloration. Chilled, filtered, washed with acetone and water and dried.
- Example 22 (3-ethyl-2-benzoxazole)-(2,3-dimethyl-1-pyrrocoline) dimethinecyenine iodide 4.34 g. (1 mol.) 2-p-acetanilidovinylbenzoxazole (1 mol.) 2,3-dimethylpyrrocoline and 25 cc. glacial acetic acid were refluxed 5 minutes. Red coloration. Chilled, stirred until crystalline, again chilled and filtered. Washed with acetone and water and dried. Yield of dark red crystals 3.85 g., 87%. After recrystallization from MeOl-l, (42 c'c./g.) the dye was obtained as greenish-red needles with green-reflex melting with decomposition at 266-267". Yield 3.55 g., MeOH solution orange.
- Example 26 (3 ethyl-2-benzoxazole) (2-methyl-l-pyn'ocoline)-tetramethinecyanine iodide were refluxed 5 minutes. Blue coloration. Green crystals separated ture. Yield 2.9 grams, 64%. Disso boiling mix-.
- cresol (m and p mixture) heated to filter- 7 ed hot, cooled and diluted with 250 cc. CHaOH.
- filter layers and anti-halation layers For the preparation of overcoating layers, filter layers and anti-halation layers, according to our invention, from 50 mg. to mg. or dye are dissolved in from 2 'to 5 cc. of a water-miscible solvent. Methanol or acetone are suitable for this purpose but pyridine or Cellosolve may also be used. The solution is then added to about-25 mixture coated on be converted into cc. of a 5% gelatin solution at 40 C. and the the support. 11' the dye is too may conveniently the chloride, using cresol as a solvent for the conversion.
- a support III of any suitable cellulose nitrate or cellulose resinous material, or opaque material such as paper is coated with an emulsion layer II and an overcoating layer l2 containing apyrrole' polymethine invention.
- Fig. 2 illustrates a multi-layer photographic element for color photography in which the support 10 is coated. with sensitive layers l3, l4
- emulsion layers l3 l6 containing a red between the layers containing a yell serve purposes well known in color photography of preventing exposure of a lower layer of the element by light which the filter layers absorb.
- the pyrrole polymethine dyes used may also absorb light in other regions, such as ultra-violet light.
- Fig. 3 represents a film having an anti-halation layer containing a pyrrole polymethine dye according to our invention.
- the support to contains an emulsion layer H on one side and an anti-halation layer l8 containing the pyrrole dye on the opposite side.
- the dyes may be dis-' persed in gelatin, collodion, gum arabic, synthetic resins or other suitable colloid or they may be dispersed in photographic emulsions such as gelatino silver halide emulsions and may be coated in any suitable manner.
- a photographic element comprising a sensitive layer and a light absorbing layer containing a. dye having the following formula:
- Z the non-metallic atoms necessary to complete a heterocyclic nucleus
- J the nonmetallic atoms necessary to complete a pyrrole nucleus
- R hydrogen, alkyl, or a chemical bond of a pyridine ring
- R alkyl
- R" hydrogen, alkyl, aryl, or a chemical bond of the same pyridine ring as R
- d a positive integer of from 2 to 3
- X an acid radical.
- a sensitive photographic element comprising a filter layer containing a dye having the general formula expressed in claim 1.
- a sensitive photographic element comprising a filter layer containing a (3-alkyl-2-benzoxazole) (ii-pyrrole) dimethinecyanine salt.
- a sensitive photographic element comprising a, filter layer containing a (3-a1kyI 2-benzothiazole) (ii-pyrrole) dimethinecyanine salt.
- a sensitive photographic element comprising a filter layer containing a (3-alkyl-2-benzoxazole) (1 lauryl 2 ,5 dimethyl 3 pyrrole) dimethinecyanine salt.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Laminated Bodies (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5262/39A GB529440A (en) | 1939-02-17 | 1939-02-17 | Improvements in and relating to photographic elements having light screening substances therein |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2298731A true US2298731A (en) | 1942-10-13 |
Family
ID=9792773
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US317726A Expired - Lifetime US2298731A (en) | 1939-02-17 | 1940-02-07 | Pyrrole filter and backing dye |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2298731A (enrdf_load_stackoverflow) |
| BE (1) | BE466374A (enrdf_load_stackoverflow) |
| DE (1) | DE729267C (enrdf_load_stackoverflow) |
| FR (2) | FR867411A (enrdf_load_stackoverflow) |
| GB (1) | GB529440A (enrdf_load_stackoverflow) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2496843A (en) * | 1948-03-10 | 1950-02-07 | Gen Aniline & Film Corp | Photographic elements containing hydroxy heavy metal salts of trinuclear iminol cyanine dyes as filter and antihalation dyes |
| US2503775A (en) * | 1947-03-21 | 1950-04-11 | Eastman Kodak Co | Pyrrolocyanine dyes containing a carboxyalkyl or sulfoalkyl group |
| US2515912A (en) * | 1946-10-01 | 1950-07-18 | Eastman Kodak Co | Pyrrole dimethinecyanine dyes |
| US2622082A (en) * | 1948-09-02 | 1952-12-16 | Eastman Kodak Co | Styryl photographic filter and antihalation dyes |
| US2968557A (en) * | 1955-12-23 | 1961-01-17 | Agfa Ag | Photographic filter layer |
| US2979501A (en) * | 1959-05-18 | 1961-04-11 | Ilford Ltd | Methin dyes containing pyrroline nuclei |
| US2984663A (en) * | 1958-06-04 | 1961-05-16 | Ilford Ltd | Methin dyes containing hydroxypyrroline nuclei |
| US3050393A (en) * | 1959-06-26 | 1962-08-21 | Ilford Ltd | Filter layer for photographic elements |
| US3099630A (en) * | 1955-11-15 | 1963-07-30 | Monsanto Chemicals | Water-soluble polymethine salts |
| US3294539A (en) * | 1963-07-03 | 1966-12-27 | Eastman Kodak Co | Light-filtering dyes for photographic elements |
| US3652283A (en) * | 1968-05-13 | 1972-03-28 | Gaf Corp | Photographic materials containing anti-halation dyestuffs |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2511222A (en) * | 1946-10-01 | 1950-06-13 | Eastman Kodak Co | Pyrrocoline polymethinecyanine dyes |
| US2515905A (en) * | 1946-10-05 | 1950-07-18 | Eastman Kodak Co | Pyrrole dimethinecyanine dyes |
| US2571775A (en) * | 1948-04-03 | 1951-10-16 | Eastman Kodak Co | Pyrro-colinocarbocyanine dyes and process for the preparation thereof |
| US2695233A (en) * | 1950-12-09 | 1954-11-23 | Gen Aniline & Film Corp | Irreversibly dischargeable photographic filter layers and method of processing film containing the same |
| US2725378A (en) * | 1951-09-19 | 1955-11-29 | Eastman Kodak Co | Pyrrole dyes and methods of making them |
| US2739148A (en) * | 1951-09-19 | 1956-03-20 | Eastman Kodak Co | Cyanine dyes containing a 3,5-diarylpyrrole nucleus and process of preparation |
| BE515452A (enrdf_load_stackoverflow) * | 1951-11-14 | |||
| US2719088A (en) * | 1951-11-14 | 1955-09-27 | Eastman Kodak Co | Photographic element containing silver salt-forming bleachable filter dyes |
| BE523921A (enrdf_load_stackoverflow) * | 1952-10-31 | |||
| US2706193A (en) * | 1952-11-22 | 1955-04-12 | Eastman Kodak Co | Merocyanine dyes and method of making them |
| USD586008S1 (en) | 2007-03-15 | 2009-02-03 | Boral Lifefile, Inc. | Roof tile |
-
0
- DE DENDAT729267D patent/DE729267C/de active Active
- BE BE466374D patent/BE466374A/xx unknown
-
1939
- 1939-02-17 GB GB5262/39A patent/GB529440A/en not_active Expired
-
1940
- 1940-02-07 US US317726A patent/US2298731A/en not_active Expired - Lifetime
- 1940-02-16 FR FR867411D patent/FR867411A/fr not_active Expired
-
1941
- 1941-02-07 FR FR51568D patent/FR51568E/fr not_active Expired
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2515912A (en) * | 1946-10-01 | 1950-07-18 | Eastman Kodak Co | Pyrrole dimethinecyanine dyes |
| US2503775A (en) * | 1947-03-21 | 1950-04-11 | Eastman Kodak Co | Pyrrolocyanine dyes containing a carboxyalkyl or sulfoalkyl group |
| US2496843A (en) * | 1948-03-10 | 1950-02-07 | Gen Aniline & Film Corp | Photographic elements containing hydroxy heavy metal salts of trinuclear iminol cyanine dyes as filter and antihalation dyes |
| US2622082A (en) * | 1948-09-02 | 1952-12-16 | Eastman Kodak Co | Styryl photographic filter and antihalation dyes |
| US3099630A (en) * | 1955-11-15 | 1963-07-30 | Monsanto Chemicals | Water-soluble polymethine salts |
| US2968557A (en) * | 1955-12-23 | 1961-01-17 | Agfa Ag | Photographic filter layer |
| US2984663A (en) * | 1958-06-04 | 1961-05-16 | Ilford Ltd | Methin dyes containing hydroxypyrroline nuclei |
| US2979501A (en) * | 1959-05-18 | 1961-04-11 | Ilford Ltd | Methin dyes containing pyrroline nuclei |
| US3050393A (en) * | 1959-06-26 | 1962-08-21 | Ilford Ltd | Filter layer for photographic elements |
| US3294539A (en) * | 1963-07-03 | 1966-12-27 | Eastman Kodak Co | Light-filtering dyes for photographic elements |
| US3652283A (en) * | 1968-05-13 | 1972-03-28 | Gaf Corp | Photographic materials containing anti-halation dyestuffs |
Also Published As
| Publication number | Publication date |
|---|---|
| FR867411A (fr) | 1941-10-27 |
| BE466374A (enrdf_load_stackoverflow) | |
| GB529440A (en) | 1940-11-21 |
| FR51568E (fr) | 1943-02-05 |
| DE729267C (de) |
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