WO1996035142A1 - Stable antihalation materials for photographic and photothermographic elements - Google Patents
Stable antihalation materials for photographic and photothermographic elements Download PDFInfo
- Publication number
- WO1996035142A1 WO1996035142A1 PCT/US1996/003764 US9603764W WO9635142A1 WO 1996035142 A1 WO1996035142 A1 WO 1996035142A1 US 9603764 W US9603764 W US 9603764W WO 9635142 A1 WO9635142 A1 WO 9635142A1
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- WO
- WIPO (PCT)
- Prior art keywords
- dye
- acid
- carbon atoms
- antihalation
- group
- Prior art date
Links
- 239000000463 material Substances 0.000 title claims abstract description 27
- 239000002253 acid Substances 0.000 claims abstract description 51
- 239000002216 antistatic agent Substances 0.000 claims abstract description 36
- 238000000576 coating method Methods 0.000 claims abstract description 29
- 238000002835 absorbance Methods 0.000 claims abstract description 20
- 239000011248 coating agent Substances 0.000 claims abstract description 20
- -1 silver halide Chemical class 0.000 claims abstract description 19
- 150000001412 amines Chemical class 0.000 claims abstract description 12
- 230000003287 optical effect Effects 0.000 claims abstract description 10
- 239000004332 silver Substances 0.000 claims abstract description 9
- 229910052709 silver Inorganic materials 0.000 claims abstract description 9
- 230000005855 radiation Effects 0.000 claims abstract description 8
- 230000005540 biological transmission Effects 0.000 claims abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- PWDUSMIDLAJXPJ-UHFFFAOYSA-N 2,3-dihydro-1h-perimidine Chemical compound C1=CC(NCN2)=C3C2=CC=CC3=C1 PWDUSMIDLAJXPJ-UHFFFAOYSA-N 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 125000005257 alkyl acyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- AAQTWLBJPNLKHT-UHFFFAOYSA-N 1H-perimidine Chemical compound N1C=NC2=CC=CC3=CC=CC1=C32 AAQTWLBJPNLKHT-UHFFFAOYSA-N 0.000 claims 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 1
- 239000000975 dye Substances 0.000 description 140
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 13
- 230000009102 absorption Effects 0.000 description 13
- 238000010521 absorption reaction Methods 0.000 description 13
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 13
- 150000007513 acids Chemical class 0.000 description 11
- 125000003277 amino group Chemical group 0.000 description 7
- 239000011324 bead Substances 0.000 description 7
- 239000011230 binding agent Substances 0.000 description 7
- 238000003384 imaging method Methods 0.000 description 7
- 230000003068 static effect Effects 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- 238000006243 chemical reaction Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- YFOOEYJGMMJJLS-UHFFFAOYSA-N 1,8-diaminonaphthalene Chemical compound C1=CC(N)=C2C(N)=CC=CC2=C1 YFOOEYJGMMJJLS-UHFFFAOYSA-N 0.000 description 5
- 239000005711 Benzoic acid Substances 0.000 description 5
- 235000010233 benzoic acid Nutrition 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 238000010348 incorporation Methods 0.000 description 4
- 150000003951 lactams Chemical group 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- WZHHYIOUKQNLQM-UHFFFAOYSA-N 3,4,5,6-tetrachlorophthalic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O WZHHYIOUKQNLQM-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000004061 bleaching Methods 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- QZXCCPZJCKEPSA-UHFFFAOYSA-N chlorfenac Chemical compound OC(=O)CC1=C(Cl)C=CC(Cl)=C1Cl QZXCCPZJCKEPSA-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 230000005611 electricity Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000000670 limiting effect Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 2
- JEZQCHJJLYRNOZ-UHFFFAOYSA-N 2-benzoyl-3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1C(=O)C1=CC=CC=C1 JEZQCHJJLYRNOZ-UHFFFAOYSA-N 0.000 description 2
- CWJJAFQCTXFSTA-UHFFFAOYSA-N 4-methylphthalic acid Chemical compound CC1=CC=C(C(O)=O)C(C(O)=O)=C1 CWJJAFQCTXFSTA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229920001481 poly(stearyl methacrylate) Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000009895 reductive bleaching Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 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 2
- GDIYMWAMJKRXRE-UHFFFAOYSA-N (2z)-2-[(2e)-2-[2-chloro-3-[(z)-2-(1,3,3-trimethylindol-1-ium-2-yl)ethenyl]cyclohex-2-en-1-ylidene]ethylidene]-1,3,3-trimethylindole Chemical compound CC1(C)C2=CC=CC=C2N(C)C1=CC=C1C(Cl)=C(C=CC=2C(C3=CC=CC=C3[N+]=2C)(C)C)CCC1 GDIYMWAMJKRXRE-UHFFFAOYSA-N 0.000 description 1
- AIGNCQCMONAWOL-UHFFFAOYSA-N 1,3-benzoselenazole Chemical class C1=CC=C2[se]C=NC2=C1 AIGNCQCMONAWOL-UHFFFAOYSA-N 0.000 description 1
- IHXWECHPYNPJRR-UHFFFAOYSA-N 3-hydroxycyclobut-2-en-1-one Chemical compound OC1=CC(=O)C1 IHXWECHPYNPJRR-UHFFFAOYSA-N 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- RFAZFSACZIVZDV-UHFFFAOYSA-N butan-2-one Chemical group CCC(C)=O.CCC(C)=O RFAZFSACZIVZDV-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
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- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine group Chemical group N1=CCC2=CC=CC=C12 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- JHJNPOSPVGRIAN-SFHVURJKSA-N n-[3-[(1s)-1-[[6-(3,4-dimethoxyphenyl)pyrazin-2-yl]amino]ethyl]phenyl]-5-methylpyridine-3-carboxamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=CN=CC(N[C@@H](C)C=2C=C(NC(=O)C=3C=C(C)C=NC=3)C=CC=2)=N1 JHJNPOSPVGRIAN-SFHVURJKSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000007344 nucleophilic reaction Methods 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
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- 230000003595 spectral effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 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
- G03C1/494—Silver salt compositions other than silver halide emulsions; Photothermographic systems ; Thermographic systems using noble metal compounds
- G03C1/498—Photothermographic systems, e.g. dry silver
- G03C1/49872—Aspects relating to non-photosensitive layers, e.g. intermediate protective layers
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/007—Squaraine dyes
-
- 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
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/008—Dyes containing a substituent, which contains a silicium 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
- G03C1/76—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
- G03C1/85—Photosensitive materials characterised by the base or auxiliary layers characterised by antistatic additives or coatings
- G03C1/89—Macromolecular substances 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
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/16—X-ray, infrared, or ultraviolet ray processes
- G03C5/164—Infra-red processes
-
- 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
- Y10S430/145—Infrared
Definitions
- This invention relates to the stabilization of dyes useful as antihalation and acutance materials for photographic and photothermographic elements when those dyes are combined in solution with antistatic agents having groups capable of accepting a proton (a basic material) from or capable of nucleophilic reaction with the conjugated portions of the antihalation dye and thereby altering the spectral absorbance of that dye .
- Light-sensitive recording materials such as photographic and photo ⁇ thermographic elements, frequently suffer from a phenomenon known as halation which causes degradation in the quality of the recorded image.
- These light sensitive recording materials typically comprise a photosensitive layer and a substrate such as film base. Image quality degradation occurs when a fraction of the imaging light which strikes the photosensitive layer is not absorbed, but instead passes through to the film base on which the photosensitive layer is coated. A portion of the light reaching the base may be reflected back to strike the photosensitive layer from the underside. This reflected light may, in some cases, contribute significantly to the total exposure of the photosensitive layer. Any particulate matter (including silver halide grains) in the photosensitive element may also cause light passing through the element to be scattered.
- a dye which absorbs light that has been scattered within the coating and would otherwise lead to reduced image sharpness.
- the absorption of this dye must be at about the same wavelength as the sensitivity of the photosensitive layer.
- a light- absorbing layer is frequently coated in a separate backing layer or under layer on the reverse side of the support from the photosensitive layer.
- Such a coating known as an "antihalation layer” effectively reduces reflection of light which has passed through the photosensitive layer.
- a similar effect may be achieved by interposing a light-absorbing layer between the photosensitive layer and the substrate.
- This construction known in the art as an “antihalation under layer” is applicable to photosensitive coatings on non-transparent as well as on transparent supports.
- a light-absorbing substance may also be incorporated into the photo ⁇ sensitive layer itself in order to absorb scattered light.
- Substances used for this purpose are known as "acutance dyes.” Essentially any dye which absorbs light at the wavelength of interest can be used as an antihalation dye, and potentially, as an acutance dye. The restraints on the choice of acutance dyes are greater as the dye must not interfere with the imaging chemistry. Typically this means that the dye cannot cause fogging of the silver in the imaging layer.
- Some recent patents dealing with antihalation and acutance dyes include US 4,581,325; EP 0,102,781 A2; EP 0,377,961 Al; EP 0,329,491 A2; EP 0,397,435 Al. Many substances are known which absorb visible and/or ultraviolet light, and many are suitable for image improvement purposes in conventional photo ⁇ graphic elements sensitized to wavelengths below 700 nm.
- U.S. Patent 4,581,325 discloses a group of heptamethine cyanine dyes having a cyclopentene ring in the polymethine chain which are suitable for use as antihalation or acutance dyes in both photographic and photothermographic elements.
- European Patent Application 377961 discloses use of polymethine dyes of a particular formula as alternative near-infrared antihalation or acutance dyes in either photographic or photothermographic elements.
- these dyes also have tails or some absorption in the visible region of the spectrum and, thus, display a slight purple tint. This tint is undesirable and prevents production of the photographic or photothermographic elements using a clear support or film base. Instead a film base with a slight tint is used to counteract the tint of the antihalation or acutance dye.
- European Patent Application 569 857 discloses dyes which may be used as infrared or near infrared antihalation dyes in photographic elements. However, once again, the reference teaches that the dyes must be decolored or dissolved out during photographic processing.
- U.S. Patent 5,380,635 discloses that dihydroperimidine squarylium dyes are useful in antihalation layers or as acutance dyes in a photothermographic (dry silver) or photographic element. These dyes absorb radiation in the near-infrared region, from 750 to 850 nm, and impart only a very low degree of visible coloration to the photographic or photothermographic element, while improving image sharpness. The coloration that is imparted to the photographic or photothermographic element by these dyes tends to be quite neutral, frequently gray or grayish-brown. Thus, use of dihydroperimidine squarylium dyes as antihalation or acutance dyes enables use of clear supports or base films in the radiation sensitive elements.
- antistatic agents into layers in photographic or photothermographic elements to reduce static electricity buildup.
- Static electricity is well known to interfere with both material handling of imageable elements and with the quality of the image itself.
- imageable elements are radiation-sensitive (e.g., light-sensitive)
- the discharge of static electricity as a spark can cause spurious images on the light-sensitive element.
- This is clearly undesirable, and is in part avoided by the addition of antistatic materials or layers into imageable elements.
- the addition of basic antistatic agents into antihalation layers can and often does react with the antihalation dye by changing the saturation of the dye and thereby changing the critical absorption characteristics of the dye and reducing its effectiveness or even adding spurious color to the element.
- Antihalation coating solutions comprising both antihalation dyes and basic (or base containing) antistatic agents in a binder can display reduced reduction in the optical density of the antihalation dye at its primary (maximum) wavelength of absorption when an acid having a pKa of less than 4.2 is added to the antihalation solution before coating.
- This invention is particularly effective when amine- containing antistatic agents (either with amine groups in the antistat or as residues from the synthesis of the antistatic agents) are used as the antistatic agents.
- the problem has been found to be particularly acute with squarylium dyes, although the absorption altering reaction can clearly occur with any dye having conjugation in the dye structure which can be altered by a base (such as a free amine).
- a preferred aspect of the present invention provides photosensitive element comprising a support bearing an electromagnetic-radiation-sensitive photographic silver halide material and a dihydroperimidine squarylium dye having the nucleus:
- a basic antistatic agent a basic antistatic agent, and an acid having a pKa of less than 4.2 in an amount sufficient to reduce the rate of reaction of the basic antistatic agent with the dye which causes wavelength changes in the absorption characteristics of said dye.
- the dihydroperimidine squarylium dyes used as antihalation or acutance dyes have the general formula:
- R 1 , R 4 , R J , and R 8 each independently represent hydrogen, an alkyl group having from 1-20 carbon atoms, a cycloalkyl group having from 1-20 carbon atoms, an aryl group having up to 14 carbon atoms, an aralkyl group
- R 1 and R 2 , and/or R 3 and R 4 , and/or R 5 and R 6 and/or R 7 and R 8 ; or R 2 and R 3 and/or R 6 and R 7 are bonded together to form a 5-, 6-, or 7-membered ring.
- antihalation layers are needed for photothermographic films. These layers contain a dye which absorbs at the exposure wavelength, reducing reflected light within the construction.
- a particularly useful class of antihalation dyes are the bis(dihydroperimidine) squarylium dyes, which are the subject of U.S. Patent No. 5,380,635.
- This invention relates to pot-life stabilization of bis(dihydro- perimidine) squarylium dyes when using amine antistatic agents. Certain acids have been found to minimize the bleaching of the dyes in solution, before coating, without adversely affecting the antistatic properties of the coated film.
- Preferred antistatic agents of the invention are quaternary ammonium compounds which exhibit an affinity for water molecules, which in turn serve to reduce the surface resistivity of the materials into which they are added. The behavior of these antistatic agents within a solution is dependent on the overall composition of these compounds.
- Examples of these quaternary ammonium antistatic agents include alkoxylated (here, ethoxylated is shown) tertiary amines of a general structure: R,-N(CH 2 CH 2 OH) 2 in which R, represents a relatively long-chain alkyl group (e.g., greater than 5 carbon atoms, inclusive of 20, 30 or more carbon atoms).
- the simplest amine salt antistatic agents are those of the formula:
- each R u independently represents an alkyl group of 8 to 30 atoms, preferably of 10 to 24 carbon atoms; and the anion X " is typically methyl or ethyl sulfate.
- the preferred amine antistatic agents used in the practice of the present invention are highly-fluorinated alkyl sulfonyl amine terminated polyoxyalkylene antistatic agents. These materials may generally be represented by the formula: R f SOf H 3 N— Q— NH 3 + O 3 SR wherein:
- R f is a highly fluorinated group (e.g., highly fluorinated or perfluorinated alkyl or aryl) highly fluorinated indicating that at least 65% of all substitutents on carbon atoms within the group are fluorine;
- Q is a divalent polyoxyalkylene group (e.g., polyoxyethylene, poly- oxypropylene) such as — ⁇ CH 2 CH 2 O) seldom— , — (CH 2 CH 2 CH 2 O) forum— , and the like; and n is an integer of at least 1 and preferably between 2 and 30, more preferably between 2 and 18.
- polyoxyalkylene group e.g., polyoxyethylene, poly- oxypropylene
- the acids used in the practice of the present invention are preferably organic acids having a pKa of less than about 4.2.
- useful acids include acetic acid, benzoic acid, 4-methylphthalic acid, tetrachlorophthalic acid, chlorobenzoyl- benzoic acid, and trichloroacetic acid, and the like.
- Organic acids such as benzoic acid (pKa of 4.19) and acetic acid (pKa of 4.75) have been found to be somewhat useful, and show some benefit in reducing bleaching of the antihalation dye but may require large amounts to be effective.
- the acids have a pKa of less than about 3.5 and more preferred that they have a pKa of less than about 3.0 for the practice of the present invention.
- the acids should be used in an amount that can measurably reduce the change in optical density of the antihalation dye solution over a 24 hour period (e.g., reduce the change in optical density at the wavelength of absorbance by at least 0.1 over said 24 hour period at ambient conditions).
- the acids are added into the coating composition at any time before coating. For maximum effectiveness, they are preferably added before addition of the antistatic agent. They are added in the functionally effective amounts described above which may be in the range of at least 0.50 mole equivalent of acid to 1 mole equivalent of each amine group in the antistatic agent, preferably at least 1.0 mole equivalent of acid to 1 mole equivalent of each amine group in the antistatic agent, more preferably , 1.5 mole equivalent of acid to 1 mole equivalent of each amine group in the antistatic agent.
- the acid may be used in any amount over this minimum, but should not flood the composition of the layer and destroy its beneficial physical properties. For example, there would be a practical limit of 10: 1 mole ratio of acid to antistatic agent in the antihalation layer solution.
- the pKa's of representative organic acids are shown below.
- alkyl group is intended to include not only pure open-chain and cyclic saturated hydrocarbon alkyl substituents, such as methyl, ethyl, propyl, t-butyl, cyclohexyl, adamantyl, octadecyl, and the like, but also alkyl substituents bearing further substituents known in the art, such as hydroxyl, alkoxy, vinyl, phenyl, halogen atoms (F, Cl, Br, and I), cyano, nitro, amino, carboxyl, ethers (e.g. CH 3 CH 2 OCH 2 -), etc.
- alkyl moiety is limited to the inclusion of only pure open- chain and cyclic saturated hydrocarbon alkyl substituents, such as methyl, ethyl, propyl, /-butyl, cyclohexyl, adamantyl, octadecyl, and the like.
- Substituents which react with active ingredients, such as very strongly electrophilic or oxidizing substituents, would of course be excluded by the ordinary skilled artisan as not being inert or harmless.
- any substitution which does not alter the bond structure of the formula or the shown atoms within that structure is included within that structure.
- substituent groups may be placed on the chain or on the heterocyclic nucleus, but the conjugation of the chain may not be altered and the atoms shown in the heterocyclic nuclei may not be replaced.
- infrared (or red) antihalation dye such as merocyanines, cyanines, (e.g., indolenines, benzotriazoles, benzoselenazoles, benzimidazoles, oxazoles, etc.) squaryliums, etc. and other known infrared (and red) absorbing dyes which could be used in photographic and photothermographic elements.
- merocyanines cyanines
- cyanines e.g., indolenines, benzotriazoles, benzoselenazoles, benzimidazoles, oxazoles, etc.
- red absorbing dyes which could be used in photographic and photothermographic elements.
- the preferred dyes for use as an antihalation dye are the squarylium dyes disclosed in U.S. Patent No. 5,380,635.
- the photosensitive elements of this invention preferably include as acutance or antihalation dyes, dihydroperimidine squarylium dyes of the formulas set forth above.
- R 1 , R 4 , R 5 , and R 8 are hydrogen and R 2 , R 3 , R 6 , and R 7 independently represent alkyl groups having from 1-20 carbon atoms, a cycloalkyl group having from 1-20 carbon atoms, an aralkyl group, an aryl group, or R 2 and R 3 taken together and R 6 and R 7 taken together form 5-, 6-, or 7-membered rings.
- Representative, non-limiting dyes according to this preferred embodiment are:
- R 3 and R 4 are taken together and R 7 and R 8 are taken together to form cycloalkyl groups having 1-20 carbon atoms, R 2 and R 6 are aryl groups, and R 1 and R 5 are hydrogen.
- a preferred but non-limiting example includes:
- R 3 and R 4 are taken together and R 7 and R 8 are taken together to form lactam groups, R 2 and R 6 are alkyl or aryl groups and R 1 and R J are H.
- Representative dyes according to this embodiment are:
- R is an alkyl group of 1 to 20, preferably 4 to 20, carbon atoms.
- exemplary R groups include but are not limited to propyl, butyl, pentyl, octyl, -CH 3 -O-CH 2 CH 3 , -CH 2 -O-CH 2 CH 2 -O-CH 3 , etc.
- R 1 , R 4 , R s , and R 8 as hydrogen and R 2 , R 3 , R 6 , and R 7 as -CH 2 OR 9 wherein R 9 is either -SiRR'R'", where R', R", and R'" independently represent an alkyl group of 1 to 20 carbon atoms, or -SO 2 R 10 where R 10 is an alkyl group of 1 to 20, preferably 4 to 20 carbon atoms.
- R 9 is either -SiRR'R'", where R', R", and R'" independently represent an alkyl group of 1 to 20 carbon atoms, or -SO 2 R 10 where R 10 is an alkyl group of 1 to 20, preferably 4 to 20 carbon atoms.
- Nonlimiting examples of such embodiments are:
- dyes suitable for use as near infrared antihalation or acutance dyes may include dyes wherein R 1 and R 2 , R 3 and R 4 , R 5 and R 6 , and R 7 and R 8 are taken together to form cycloalkyl groups.
- Dyes of this type can be prepared by reaction of a ⁇ , ⁇ -dihaloketone with a 1,8-diamino- naphthalene, followed by condensation with squaric acid.
- dyes suitable for use as antihalation or acutance dyes may include, dyes wherein R 1 and R 2 , and R 5 and R 6 are taken together to form lactam groups, while R 3 and R 4 , and R 7 and R 8 are taken together to form cycloalkyl groups.
- Dyes of this type can be prepared by reaction of a ⁇ -halo-keto-carboxylic ester with a 1,8-diaminonaphthalene, followed by condensation with squaric acid.
- R ⁇ R 8 may enable one to shift the peak absorption wavelength.
- dyes of the type exemplified by structures 3a-3d have wavelength absorptions shifted 10-15 nm to shorter wavelengths from those exemplified by structures la-lf.
- the squarylium dyes exemplified by structures la-lf may be prepared by condensing a ketone or an aldehyde with a 1,8-diamino naphthalene in the presence of an acid catalyst, in a solvent such as toluene, under reflux conditions, with removal of the water from the reaction mixture as it is formed.
- the resultant dihydroperimidine product is typically isolated by distillation or crystallization.
- the dihydroperimidine is then heated at reflux with squaric acid, [also known as 3,4-dihydroxy-3-cyclobutene-l,2-dione] in a mixture of toluene and w-butanol, again with removal of the liberated water as it is formed.
- squaric acid [also known as 3,4-dihydroxy-3-cyclobutene-l,2-dione] in a mixture of toluene and w-butanol, again with removal of the liberated water
- Dyes in which R 3 and R 4 and R 7 and R 8 form carbocyclic rings are similarly prepared.
- condensation of a ⁇ -haloketone with a 1,8-diaminonaphthalene gives a ring fused dihydroperimidine.
- Reaction of this material with squaric acid gives dyes exemplified by structure 2a.
- the preparation of dyes of this type is shown in Scheme 2.
- n is an integer which represents the number of methine groups necessary to complete a 5-, 6-, or 7-membered ring.
- Dyes in which R 3 and R 4 , and R 7 and R 8 form lactam are prepared by condensing a keto-carboxylic acid derivative (typically a keto-ester) with a 1,8-diamino- naphthalene to give a lactam fused dihydroperimidine. Reaction of this material with squaric acid gives dyes exemplified by structures 3a-3d. The preparation of dyes of this type is shown in Scheme 3. In Scheme 3, m is an integer which represents the number of methine groups necessary to complete the 5-, 6-, or 7-membered ring.
- the dihydroperimidine squarylium dye may be used in an antihalation coating for photothermography or photography or it may be used as an acutance or filter dye.
- the type of photothermographic element used in the invention is not critical. Examples of suitable photothermographic elements include dry silver systems (see, for example U.S. Patent Nos. 3,457,075 and 5,258,274, both incorporated herein by reference) and diazo systems.
- the dihydroperimidine squarylium dye is usually coated together with an organic binder as a thin layer on a substrate and is present in a layer separate from the light-sensitive layer.
- the antihalation layer may be positioned above, below, or both above and below the light-sensitive layer, and if the support is transparent, an antihalation layer may be positioned on the surface of the support opposite the light-sensitive layer.
- the antihalation layer When positioned above the light sensitive layer, the antihalation layer may alternatively be called a filter layer.
- the dihydroperimidine squarylium dyes are incorporated within the light-sensitive layer according to conventional techniques. Whether used as an antihalation, acutance, or filter dye, in photographic or photothermographic elements, it is preferred to incorporate dyes in an amount sufficient to provide an optical density of from 0.05 to 3.0, more preferably from 0.1 to 2, absorbance units at ⁇ m-x of the dye.
- the coating weight of the dye is generally from 0.001 to 1 g/m 2 , preferably 0.001 to 0.05 g/m 2 .
- a wide variety of polymers are suitable for use as the binder. Non ⁇ limiting examples of these polymers include cellulose acetate butyrate, polyvinyl butyral, poly(vinylidene chloride), cellulose acetate, and various acrylic polymers. In certain situations, absorption at a variety of wavelengths may be desirable. If so, more than one dye can be used.
- the dyes may be incorporated into the photosensitive element in any known configuration. For example, each dye may be in an independent antihalation layer, more than one dye may be contained in one antihalation layer, one dye may be an acutance dye while the other is used in an antihalation layer, etc.
- Antistat-1 is CsF ⁇ SOf H 3 N-(CH 2 CH 2 O) ⁇ 2 CH 2 CH 2 NH 3 + " O 3 SCgF ⁇
- B A is benzoic acid.
- 4-MPA is 4-methylphthalic acid.
- TCPA is tetrachlorophthalic acid
- CBBA is 7-chlorobenzoylbenzoic acid.
- AA is acetic acid
- TCA is trichloroacetic acid
- CAB 381-20 is a cellulose acetate butyrate resin available from Eastman Kodak Co.
- MEK is methyl ethyl ketone (2-butanone).
- PE-200 is a polyester resin available from Shell.
- PET is poly(ethylene terephthalate).
- PMMA-13 is Beads of 13 ⁇ m polymethylmethacrylate.
- PSMA-8 Beads are 8 ⁇ m polystearylmethacrylate bead.
- PSMA-13 Beads are 13 ⁇ m are polystearyl methacrylate beads.
- Samples 2-1 to 2-8 were prepared with a dihydroperimidine squarylium dye incorporated into an antihalation coating. Each solution contained the following materials. Material Amount
- Antistat- 1 0.180 g dissolved in
- the coatings were tested immediately after coating and drying for absorbance. The coatings were then stored for 24 hours at 70°F/20%RH and tested for conductivity properties.
- Resistivity of each coating was measured on the Keithly 6105 surface resistivity meter. Incorporation of acid into the antihalation coatings appears to have little affect on the resistivity.
- the 0% charge decay time indicates the time (in seconds) necessary to dissipate 100% of the charge (i.e., have 0% of the initial charge remaining). A short decay time is desired.
- the 10% charge decay time indicates the time (in seconds) necessary to dissipate 90% of the electrical charge (i.e., have 10% of the initial charge remaining). A short decay time is desired.
- the 50% charge decay time indicates the time (in seconds) necessary to dissipate 50% of the electrical charge, (i.e., have 50% of the initial charge remaining). A short decay time is desired. Incorporation of acid into the antihalation coatings appears to have little affect on the charge decay time.
- Dye 4a (12 mg) and the acid given below were dissolved in 9.00 g of a 1.0 % solution of Antistat-1 in 2-butanone. 1 mL of this solution was diluted to 250 mL with 2-butanone and the absorbance at 806 nm ( ⁇ max) measured. The remainder of the undiluted solution was kept at room temperature. After 24 hr, 1 mL of this solution was again diluted to 250 mL with 2-butanone and the absorbance again measured.
- An antihalation binder solution premix was prepared as follows:
- An antihalation coating solution was prepared as follows:
Abstract
Description
Claims
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EP96909791A EP0824718A1 (en) | 1995-05-01 | 1996-03-21 | Stable antihalation materials for photographic and photothermographic elements |
JP8533293A JPH11505624A (en) | 1995-05-01 | 1996-03-21 | Stable antihalation material for photographic and photothermographic elements |
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US08/431,734 US6329128B1 (en) | 1995-05-01 | 1995-05-01 | Stable antihalation materials for photographic and photothermographic elements |
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US6431448B1 (en) | 2000-05-11 | 2002-08-13 | Eastman Kodak Company | Keyed data-and-print album page |
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US6762013B2 (en) | 2002-10-04 | 2004-07-13 | Eastman Kodak Company | Thermally developable materials containing fluorochemical conductive layers |
JP5353155B2 (en) * | 2008-09-25 | 2013-11-27 | 富士ゼロックス株式会社 | Image forming material |
US9193869B2 (en) | 2013-08-26 | 2015-11-24 | Xerox Corporation | Dye compounds, method of making the compounds and ink composition employing the compounds |
US9738811B2 (en) | 2013-08-26 | 2017-08-22 | Xerox Corporation | Phase change inks containing wax-soluble near-infrared dyes |
US8884012B1 (en) | 2013-08-26 | 2014-11-11 | Xerox Corporation | Dye compound and method of making the compound |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4070189A (en) * | 1976-10-04 | 1978-01-24 | Eastman Kodak Company | Silver halide element with an antistatic layer |
US4839265A (en) * | 1985-08-08 | 1989-06-13 | Fuji Photo Film Co., Ltd. | Silver halide photosensitive material containing an infrared absorption dye |
EP0569857A1 (en) * | 1992-05-11 | 1993-11-18 | Fuji Photo Film Co., Ltd. | Silver halide photographic material |
US5380635A (en) * | 1994-02-28 | 1995-01-10 | Minnesota Mining And Manufacturing Company | Dihydroperimidine squarylium dyes as antihalation and acutance materials for photographic and photothermographic articles |
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JPS5146755B1 (en) * | 1970-08-05 | 1976-12-10 | ||
US3811887A (en) * | 1970-12-18 | 1974-05-21 | Konishiroku Photo Ind | Photographic material comprising bisacylhydrazinium compounds |
US5395747A (en) * | 1993-12-20 | 1995-03-07 | Minnesota Mining & Manufacturing Company | Stabilized thermal-dye-bleach constructions |
-
1995
- 1995-05-01 US US08/431,734 patent/US6329128B1/en not_active Expired - Fee Related
-
1996
- 1996-03-21 EP EP96909791A patent/EP0824718A1/en not_active Withdrawn
- 1996-03-21 WO PCT/US1996/003764 patent/WO1996035142A1/en not_active Application Discontinuation
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4070189A (en) * | 1976-10-04 | 1978-01-24 | Eastman Kodak Company | Silver halide element with an antistatic layer |
US4839265A (en) * | 1985-08-08 | 1989-06-13 | Fuji Photo Film Co., Ltd. | Silver halide photosensitive material containing an infrared absorption dye |
EP0569857A1 (en) * | 1992-05-11 | 1993-11-18 | Fuji Photo Film Co., Ltd. | Silver halide photographic material |
US5380635A (en) * | 1994-02-28 | 1995-01-10 | Minnesota Mining And Manufacturing Company | Dihydroperimidine squarylium dyes as antihalation and acutance materials for photographic and photothermographic articles |
Cited By (1)
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US6431448B1 (en) | 2000-05-11 | 2002-08-13 | Eastman Kodak Company | Keyed data-and-print album page |
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