US3700455A - Color photograph containing fade-preventing agents - Google Patents
Color photograph containing fade-preventing agents Download PDFInfo
- Publication number
- US3700455A US3700455A US68534A US3700455DA US3700455A US 3700455 A US3700455 A US 3700455A US 68534 A US68534 A US 68534A US 3700455D A US3700455D A US 3700455DA US 3700455 A US3700455 A US 3700455A
- Authority
- US
- United States
- Prior art keywords
- color
- color image
- agent
- fading
- coupler
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- -1 SILVER HALIDE Chemical class 0.000 abstract description 16
- 239000006096 absorbing agent Substances 0.000 abstract description 14
- 239000004332 silver Substances 0.000 abstract description 12
- 229910052709 silver Inorganic materials 0.000 abstract description 12
- 150000001875 compounds Chemical class 0.000 abstract description 11
- 239000000203 mixture Substances 0.000 abstract description 8
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 4
- 229930195733 hydrocarbon Natural products 0.000 abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical group [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000839 emulsion Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 239000000975 dye Substances 0.000 description 10
- 239000000523 sample Substances 0.000 description 9
- 239000013068 control sample Substances 0.000 description 7
- 239000001828 Gelatine Substances 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 229920000159 gelatin Polymers 0.000 description 6
- 235000019322 gelatine Nutrition 0.000 description 6
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 4
- 229930182490 saponin Natural products 0.000 description 4
- 150000007949 saponins Chemical class 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 3
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 3
- 229910001864 baryta Inorganic materials 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229910052724 xenon Inorganic materials 0.000 description 3
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000001043 yellow dye Substances 0.000 description 2
- SLYRGJDSFOCAAI-UHFFFAOYSA-N 1,3-thiazolidin-2-one Chemical compound O=C1NCCS1 SLYRGJDSFOCAAI-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- MSZJEPVVQWJCIF-UHFFFAOYSA-N butylazanide Chemical compound CCCC[NH-] MSZJEPVVQWJCIF-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 229960002380 dibutyl phthalate Drugs 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- HKTSLDUAGCAISP-UHFFFAOYSA-N ethyl n,n-diphenylcarbamate Chemical compound C=1C=CC=CC=1N(C(=O)OCC)C1=CC=CC=C1 HKTSLDUAGCAISP-UHFFFAOYSA-N 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- RSAZYXZUJROYKR-UHFFFAOYSA-N indophenol Chemical compound C1=CC(O)=CC=C1N=C1C=CC(=O)C=C1 RSAZYXZUJROYKR-UHFFFAOYSA-N 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000005406 washing Methods 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
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/392—Additives
- G03C7/39208—Organic compounds
- G03C7/39212—Carbocyclic
- G03C7/39216—Carbocyclic with OH groups
Definitions
- R R R and R are individually a straight chain or branched-chain hydrocarbon radical having 1 to 18 carbon atoms, the total sum of carbon atoms of said R R R and R being less than 32; and X is -S, -O, SOg or where n is an integer of to 3, and R is a hydrogen atom or a lower alkyl group, and a color image-forming dye are incorporated into a silver halide photographic composition.
- R is a hydrogen atom or a lower alkyl group
- a color image-forming dye are incorporated into a silver halide photographic composition.
- An ultraviolet ray absorbing agent and/ or a color coupler may be incorporated into the composition.
- the present invention relates to a color photograph bearing a color image comprising an azomethine, indoaniline or the like dye together with a phenol derivative as a fading-preventing agent.
- a color photograph is obtained by subjecting a light-sensitive silver halide color photographic material to color development according to the oxidation condensation reaction of primary aromatic amino compound with a coupler, thereby forming a color image comprising an azomethine, indoaniline, indophenol or the like dye.
- substractive color photography is employed for reproduction of the color image, and cyan, magenta and yell-ow dyes are formed by the color development, in general.
- the cyan dye is formed from a phenol or naphthol type coupler, the magenta dye from a pyrazolone type coupler, and the yellow dye from an acylacetamide type coupler.
- an ultraviolet ray-absorbing agent in order to impart satisfactory light fa'stness to a color image by use of an ultraviolet ray-absorbing agent, a large amount of said agent agent is required, thereby the color image is greatly stained due to coloration of the ultraviolet ray-absorbing agent itself. Further, the use of an ultraviolet ray-absorbing agent is not efiective at all for prevention of the fading of color image due to visible light, and thus the improvement in light fastness of color image by use of an ultraviolet ray-absorbing agent has a limit.
- R R R and R are individually a straight chain or branched chain hydrocarbon radical having 1 to 18 carbon atoms, the total sum of carbon atoms of said R R R and R being less than 32; and X is S, -O, SO or i L ⁇ t. l.
- n is an integer of 0 to 3; and R is hydrogen atom or a lower alkyl group.
- the above-mentioned fading-preventing agent employed in the present invention is used for the improvement in light fastness of cyan, magenta and yellow color images formed by color development.
- Cyan, magenta and yellow couplers to be used for the formation of these color images are not limited, and may be any of such types that they are alkali-soluble and alkali solutions thereof are incorporated into silver halide photographic emulsions, and that they are dissolved in a high boiling organic solvent to give a solution which can be dispersed in an aqueous gelatine solution or added to silver halide photographic emulsions.
- the fading-preventing agent employed in the present invention may be incorporated into any or all of the layers of a light-sensitive silver halide photographic materials, i.e. photographic emulsion layers in which cyan, magenta and yellow dyes will be formed by color development. Further, when applied to a transfer diffusion method, the fading-preventing agent may be incorporated not only into such photographic emulsion layers as mentioned above but also into receptive layers. That is, it is suflicient that the fading-preventing agent is made present together with any or all of dyes forming the color image of a finallyobtained photograph.
- the fading-preventing agent used in the present invention is hardly water-soluble, and it is dissolved in a low boiling organic solvent such as methyl acetate, ethyl acetate, carbon tetrachloride, chloroform, methanol, ethan, n-butanol, dioxane, acetone, benzene, dimethylformamide or dimethyl sulfoxide, a high boiling solvent such tricresyl phosphate, di-n-butyl phthalate or ethyl N,N-diphenyl carbamate, or a mixed solvent comprising said low and high boiling solvents.
- a low boiling organic solvent such as methyl acetate, ethyl acetate, carbon tetrachloride, chloroform, methanol, ethan, n-butanol, dioxane, acetone, benzene, dimethylformamide or dimethyl sulfoxide
- a high boiling solvent such tric
- the resulting solution is charged into a protective colloid solution, dispersed by means of a colloid mill or a homogenizer and then added to, for example, a silver halide photographic emulsion containing a coupler.
- a protective colloid solution dispersed by means of a colloid mill or a homogenizer and then added to, for example, a silver halide photographic emulsion containing a coupler.
- the fading-preventing agent and the coupler may be dissolved in an organic solvent and then added to an aqueous gelatine solution or the like.
- the amount of the fading-preventing agent to be added varies depending on the kind of said agent and the coupler employed and on the kind of the layer to which the agent is applied, but is usually within the range from 1 to 100% by weight based on the weight of the coupler.
- a silver halide photographic emulsion containing the fading-preventing agent and a coupler is coated on a support such as baryta paper or film base to form a photographic emulsion layer.
- Into this photographic emulsion layer, or a lower or upper layer thereof, may be incorporated an ultraviolet ray-absorbing agent.
- the fading-preventing agent of the present invention can be used in combination with the ultraviolet ray-absorbing agent, whereby the light fastness of the resulting color image can be enhanced.
- UV rayabsorbing agent examples include benzophenone, acrylonitrile, thiazolidone, benzotriazole, stilbene, oxazole, thiazole and imidazole type compounds, though these are, of course, not limitative.
- the incorporation of the fading-preventing agent does not bring about any injury in the color development, and even when it is made present together with a dye formed by color development, no change in hue is observed. Moreover, the fading-preventing agent has no detrimental interactions with other photographic additives.
- EXAMPLE 1 2 g. of the exemplified compound (4) was dissolved in a mixed solution of 1 g. of tricresyl phosphate and 4 g. of ethyl acetate. The resulting solution was added to 40 cc. of a 5% aqueous gelatine solution containing saponin and then dispersed by means of a homogenizer. The whole amount of the resulting dispersion was added to 400 cc. of a silver chlorobromide emulsion containing 10 g. of sodium l-hydroxy-N-octadecyl-2-naphthamide-4-sulfonate (coupler). Thereafter, the emulsion was coated on a baryta paper and then dried to prepare a sample of the present invention.
- control sample was prepared in the same manner as above, except that the compound (4) was not used.
- the sample of the present invention and the control sample were individually exposed to white light, subjected to color development, stopping, fixing, bleaching, waterwashing and drying, and exposed for 5, l0 and 20 hours by means of a Xenon fade meter to calculate the percentage (D/D0 of the density after exposure (D) to the density before exposure (D0).
- the results were as shown in Table 1.
- EXAMPLE 2 A mixture comprising 8.0 g. of the cyan coupler 2- (p-tert-amylphenoxy-p-benzoyl)-amino 4 chloro 5- methylphenol, 3.0 g. of the exemplified compound (2) and 3.0 g. of the ultraviolet ray-absorbing agent 2-(2-hydroxy- 3,5-di-tert-butylphenol)-benzotriazo1e was dissolved in a mixed solution of 8 g. of tricresyl phosphate and 20 g. of ethyl acetate. The resulting solution was added to 200 cc. of a 5% aqueous gelatine solution containing saponin and then dispersed by means of a homogenizer.
- control sample a sample (II), and a sample (III) were prepared in the same manner as above, except that there were not used, respectively, both the exemplified compound (2) and the ultraviolet ray-absorbing agent.
- EXAMPLE 3 A mixture comprising 10 g. of the magenta coupler 1-(2,4dimethyl 6 chlorophenyl-7,3- ⁇ 3-[a-(3-pentadecylphenoxy)butylamide]benzamide ⁇ -5-pyrazolone and 4 g. of the exemplified compound (1) was dissolved in a mixed solution of 5 g. of dibutyl phthalate and 20 g. of ethyl acetate. The resulting solution was added to 200 cc. of a 5% aqueous gelatine solution containing saponin and then dispersed by means of a homogenizer. Subsequently, the dispersion was added to 350 cc. of a greensensitized silver chlorobromide emulsion, which was then coated on a baryta paper.
- Example 2 7 g. of the same ultraviolet rayabsorbing agent as in Example 2 was dissolved in a solution of 10 g. of tricresyl phosphate in 20 g. of ethyl acetate. The resulting solution was added to 300 cc. of a 10% aqueous gelatine solution containing saponin and then dispersed by means of a homogenizer. The thus obtained dispersion was coated on the aforesaid silver chlorobromide emulsion layer so that the amount of the ultraviolet ray-absorbing agent became 7 mg. per 100 cmfi, followed by drying, to prepare a sample (I).
- samples (II) and (III) and a control sample were prepared in the same manner as above, except that there were not used, respectively, the ultraviolet rayabsorbing agent, the exemplified compound (1), and both the ultraviolet ray-absorbing agent and the exemplified compound (1).
- a color composition which upon development produces a color image having improved light fastness, said composition comprising (a) a silver halide photographic emulsion (b) a compound of the formula,
- R R R and R are individually a straight chain or branched-chain hydrocarbon radical having 1 to 18 carbon atoms, the total sum of carbon atoms of said R R R and R being less than 32, and X is s -o-, or
- n is an integer of 0 to 3 and R is a hydrogen References Cited UNITED STATES PATENTS 2,688,625 9/1954 Bell et a1. 96-56 2,735,765 2/1956 Loria et a1. 96-56 3,271,156 9/ 1966 Sawdey 96-56 J. TRAVIS BROWN, Primary Examiner US. Cl. X.R.
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP44069945A JPS4831256B1 (enrdf_load_stackoverflow) | 1969-09-05 | 1969-09-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3700455A true US3700455A (en) | 1972-10-24 |
Family
ID=13417284
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US68534A Expired - Lifetime US3700455A (en) | 1969-09-05 | 1970-08-31 | Color photograph containing fade-preventing agents |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3700455A (enrdf_load_stackoverflow) |
| JP (1) | JPS4831256B1 (enrdf_load_stackoverflow) |
| DE (1) | DE2043270C3 (enrdf_load_stackoverflow) |
| GB (1) | GB1267287A (enrdf_load_stackoverflow) |
Cited By (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3936305A (en) * | 1973-12-03 | 1976-02-03 | Mitsubishi Paper Mills, Ltd. | Color photographic photosensitive material containing ultraviolet ray-absorbing compound |
| US4174220A (en) * | 1976-10-30 | 1979-11-13 | Konishiroku Photo Industry Co., Ltd. | Color photographic materials containing dye fading inhibitors |
| US4178184A (en) * | 1976-10-23 | 1979-12-11 | Konishiroku Photo Industry Co., Ltd. | Color photographic materials containing dye-fading inhibitors |
| US4266020A (en) * | 1978-10-05 | 1981-05-05 | Fuji Photo Film Co., Ltd. | Color photographic light-sensitive material |
| US4286042A (en) * | 1978-06-06 | 1981-08-25 | Fuji Photo Film Co., Ltd. | Light reflecting layer for color diffusion transfer photographic system |
| US4446219A (en) * | 1981-08-17 | 1984-05-01 | Agfa-Gevaert Aktiengesellschaft | Photographic material comprising a layer with Ni complex of 2,2'-bisphenol |
| EP0147854A2 (en) | 1983-12-29 | 1985-07-10 | Fuji Photo Film Co., Ltd. | Silver halide photographic light-sensitive materials |
| US4551422A (en) * | 1983-01-29 | 1985-11-05 | Konishiroku Photo Industry Co., Ltd. | Silver halide photographic light-sensitive material |
| EP0204175A1 (en) | 1985-05-09 | 1986-12-10 | Fuji Photo Film Co., Ltd. | Silver halide color photographic materials |
| EP0209118A2 (en) | 1985-07-17 | 1987-01-21 | Konica Corporation | Silver halide photographic material |
| EP0239363A2 (en) | 1986-03-25 | 1987-09-30 | Konica Corporation | Light-sensitive silver halide photographic material feasible for high speed processing |
| EP0242013A2 (en) | 1986-01-20 | 1987-10-21 | Konica Corporation | Silver halide color photographic light-sensitive material |
| EP0256537A2 (en) | 1986-08-15 | 1988-02-24 | Fuji Photo Film Co., Ltd. | Color print and a method for producing the same |
| US4824771A (en) * | 1986-12-18 | 1989-04-25 | Eastman Kodak Company | Photographic acetanilide couplers with novel ballast group and photographic elements containing them |
| US4983506A (en) * | 1987-10-14 | 1991-01-08 | Fuji Photo Film Co., Ltd. | Silver halide photographic material |
| US5049473A (en) * | 1988-03-17 | 1991-09-17 | Fuji Photo Film Co., Ltd. | Method of preserving colored images |
| US5108886A (en) * | 1989-12-18 | 1992-04-28 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| US5120636A (en) * | 1989-05-25 | 1992-06-09 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material containing magenta coupler, specific organic solvent and bisphenol compound |
| US5122444A (en) * | 1988-08-15 | 1992-06-16 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material containing a magenta couplers and color fading preventing agent |
| US5294529A (en) * | 1989-10-30 | 1994-03-15 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material containing magenta coupler, image-dye stabilizer and high boiling coupler solvent |
| US5437962A (en) * | 1993-04-02 | 1995-08-01 | Eastman Kodak Company | Photographic elements containing particular color couplers in combination with particular stabilizers |
| US5441855A (en) * | 1993-06-21 | 1995-08-15 | Agfa-Gevaert Ag | Color photographic recording material |
| US5466569A (en) * | 1993-06-21 | 1995-11-14 | Agfa-Gevaert Ag | Color photographic recording material |
| EP0698817A1 (en) | 1994-08-22 | 1996-02-28 | Agfa-Gevaert N.V. | Assortment of silver halide photographic industrial X-ray films and method of processing said assortment |
| US5543280A (en) * | 1994-11-24 | 1996-08-06 | Agfa-Gevaert Ag | Colour photographic recording material |
| US5561028A (en) * | 1994-06-24 | 1996-10-01 | Mitsubishi Paper Mills Limited | Silver halide photographic photosensitive material |
| EP0800113A2 (en) | 1996-04-05 | 1997-10-08 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| US6337170B1 (en) * | 1997-06-06 | 2002-01-08 | Fuji Photo Film Co., Ltd. | Color diffusion transfer image forming material |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8610610D0 (en) * | 1986-04-30 | 1986-06-04 | Kodak Ltd | Stabilization of dye images |
| DE68922547T2 (de) * | 1988-08-24 | 1995-08-17 | Fuji Photo Film Co Ltd | Farbphotographisches Silberhalogenidmaterial. |
| US5441861A (en) * | 1992-09-08 | 1995-08-15 | Agfa-Gevaert Ab | Color photographic silver halide material |
| US5891613A (en) * | 1997-08-22 | 1999-04-06 | Eastman Kodak Company | Silver halide light-sensitive element |
| US6312881B1 (en) * | 2000-01-14 | 2001-11-06 | Eastman Kodak Company | Photographic element with yellow dye-forming coupler and stabilizing compounds |
| US6555306B1 (en) | 2001-12-21 | 2003-04-29 | Eastman Kodak Company | Photographic element with dye-forming coupler and image dye stabilizing compound |
| US6846620B1 (en) | 2003-06-27 | 2005-01-25 | Albert J. Mura, Jr. | Photographic element with dye-forming coupler and image dye stabilizing coupler solvent |
-
1969
- 1969-09-05 JP JP44069945A patent/JPS4831256B1/ja active Pending
-
1970
- 1970-08-31 US US68534A patent/US3700455A/en not_active Expired - Lifetime
- 1970-09-01 DE DE2043270A patent/DE2043270C3/de not_active Expired
- 1970-09-04 GB GB42563/70A patent/GB1267287A/en not_active Expired
Cited By (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3936305A (en) * | 1973-12-03 | 1976-02-03 | Mitsubishi Paper Mills, Ltd. | Color photographic photosensitive material containing ultraviolet ray-absorbing compound |
| US4178184A (en) * | 1976-10-23 | 1979-12-11 | Konishiroku Photo Industry Co., Ltd. | Color photographic materials containing dye-fading inhibitors |
| US4174220A (en) * | 1976-10-30 | 1979-11-13 | Konishiroku Photo Industry Co., Ltd. | Color photographic materials containing dye fading inhibitors |
| US4286042A (en) * | 1978-06-06 | 1981-08-25 | Fuji Photo Film Co., Ltd. | Light reflecting layer for color diffusion transfer photographic system |
| US4266020A (en) * | 1978-10-05 | 1981-05-05 | Fuji Photo Film Co., Ltd. | Color photographic light-sensitive material |
| US4446219A (en) * | 1981-08-17 | 1984-05-01 | Agfa-Gevaert Aktiengesellschaft | Photographic material comprising a layer with Ni complex of 2,2'-bisphenol |
| US4551422A (en) * | 1983-01-29 | 1985-11-05 | Konishiroku Photo Industry Co., Ltd. | Silver halide photographic light-sensitive material |
| EP0147854A2 (en) | 1983-12-29 | 1985-07-10 | Fuji Photo Film Co., Ltd. | Silver halide photographic light-sensitive materials |
| EP0204175A1 (en) | 1985-05-09 | 1986-12-10 | Fuji Photo Film Co., Ltd. | Silver halide color photographic materials |
| EP0209118A2 (en) | 1985-07-17 | 1987-01-21 | Konica Corporation | Silver halide photographic material |
| EP0242013A2 (en) | 1986-01-20 | 1987-10-21 | Konica Corporation | Silver halide color photographic light-sensitive material |
| EP0239363A2 (en) | 1986-03-25 | 1987-09-30 | Konica Corporation | Light-sensitive silver halide photographic material feasible for high speed processing |
| EP0256537A2 (en) | 1986-08-15 | 1988-02-24 | Fuji Photo Film Co., Ltd. | Color print and a method for producing the same |
| US4824771A (en) * | 1986-12-18 | 1989-04-25 | Eastman Kodak Company | Photographic acetanilide couplers with novel ballast group and photographic elements containing them |
| US4983506A (en) * | 1987-10-14 | 1991-01-08 | Fuji Photo Film Co., Ltd. | Silver halide photographic material |
| US5049473A (en) * | 1988-03-17 | 1991-09-17 | Fuji Photo Film Co., Ltd. | Method of preserving colored images |
| US5122444A (en) * | 1988-08-15 | 1992-06-16 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material containing a magenta couplers and color fading preventing agent |
| US5120636A (en) * | 1989-05-25 | 1992-06-09 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material containing magenta coupler, specific organic solvent and bisphenol compound |
| US5294529A (en) * | 1989-10-30 | 1994-03-15 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material containing magenta coupler, image-dye stabilizer and high boiling coupler solvent |
| US5108886A (en) * | 1989-12-18 | 1992-04-28 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| US5437962A (en) * | 1993-04-02 | 1995-08-01 | Eastman Kodak Company | Photographic elements containing particular color couplers in combination with particular stabilizers |
| US5441855A (en) * | 1993-06-21 | 1995-08-15 | Agfa-Gevaert Ag | Color photographic recording material |
| US5466569A (en) * | 1993-06-21 | 1995-11-14 | Agfa-Gevaert Ag | Color photographic recording material |
| US5561028A (en) * | 1994-06-24 | 1996-10-01 | Mitsubishi Paper Mills Limited | Silver halide photographic photosensitive material |
| EP0698817A1 (en) | 1994-08-22 | 1996-02-28 | Agfa-Gevaert N.V. | Assortment of silver halide photographic industrial X-ray films and method of processing said assortment |
| US5543280A (en) * | 1994-11-24 | 1996-08-06 | Agfa-Gevaert Ag | Colour photographic recording material |
| EP0800113A2 (en) | 1996-04-05 | 1997-10-08 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
| US6337170B1 (en) * | 1997-06-06 | 2002-01-08 | Fuji Photo Film Co., Ltd. | Color diffusion transfer image forming material |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4831256B1 (enrdf_load_stackoverflow) | 1973-09-27 |
| GB1267287A (en) | 1972-03-15 |
| DE2043270C3 (de) | 1978-03-02 |
| DE2043270B2 (de) | 1977-07-07 |
| DE2043270A1 (de) | 1971-03-18 |
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