US3700454A - Light-sensitive silver halide color photographic material containing couplers and coupler solvents - Google Patents
Light-sensitive silver halide color photographic material containing couplers and coupler solvents Download PDFInfo
- Publication number
- US3700454A US3700454A US68533A US3700454DA US3700454A US 3700454 A US3700454 A US 3700454A US 68533 A US68533 A US 68533A US 3700454D A US3700454D A US 3700454DA US 3700454 A US3700454 A US 3700454A
- Authority
- US
- United States
- Prior art keywords
- coupler
- hydrogen
- alkyl
- silver halide
- general formula
- 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 title abstract description 19
- 239000002904 solvent Substances 0.000 title abstract description 18
- 239000000463 material Substances 0.000 title abstract description 17
- 229910052709 silver Inorganic materials 0.000 title abstract description 14
- 239000004332 silver Substances 0.000 title abstract description 14
- 239000006185 dispersion Substances 0.000 abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 12
- 239000001257 hydrogen Substances 0.000 abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 9
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 239000003795 chemical substances by application Substances 0.000 abstract description 6
- 239000007788 liquid Substances 0.000 abstract description 6
- 230000003647 oxidation Effects 0.000 abstract description 6
- 238000007254 oxidation reaction Methods 0.000 abstract description 6
- 239000002245 particle Substances 0.000 abstract description 6
- 230000008878 coupling Effects 0.000 abstract description 5
- 238000010168 coupling process Methods 0.000 abstract description 5
- 238000005859 coupling reaction Methods 0.000 abstract description 5
- 150000003142 primary aromatic amines Chemical class 0.000 abstract description 5
- 229960001413 acetanilide Drugs 0.000 abstract description 4
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000839 emulsion Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 8
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 8
- 239000000523 sample Substances 0.000 description 7
- 239000001828 Gelatine Substances 0.000 description 6
- 229920000159 gelatin Polymers 0.000 description 6
- 235000019322 gelatine Nutrition 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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 5
- 239000010410 layer Substances 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- QXQMENSTZKYZCE-UHFFFAOYSA-N 2-[2,4-bis(2-methylbutan-2-yl)phenoxy]acetic acid Chemical compound CCC(C)(C)C1=CC=C(OCC(O)=O)C(C(C)(C)CC)=C1 QXQMENSTZKYZCE-UHFFFAOYSA-N 0.000 description 3
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- 239000013068 control sample Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- HXJSYEGENNLCJV-UHFFFAOYSA-N 2-phenoxyheptanamide Chemical compound CCCCCC(C(N)=O)OC1=CC=CC=C1 HXJSYEGENNLCJV-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- MSZJEPVVQWJCIF-UHFFFAOYSA-N butylazanide Chemical compound CCCC[NH-] MSZJEPVVQWJCIF-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- NHQVTOYJPBRYNG-UHFFFAOYSA-M sodium;2,4,7-tri(propan-2-yl)naphthalene-1-sulfonate Chemical compound [Na+].CC(C)C1=CC(C(C)C)=C(S([O-])(=O)=O)C2=CC(C(C)C)=CC=C21 NHQVTOYJPBRYNG-UHFFFAOYSA-M 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229920006186 water-soluble synthetic resin Polymers 0.000 description 1
- 239000012866 water-soluble synthetic resin Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- 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
- G03C7/388—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor
- G03C7/3885—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor characterised by the use of a specific solvent
Definitions
- the light sensitive silver halide color photographic material comprises finely divided liquid particles containing at least one coupler which is capable of coupling with the oxidation product of a primary aromatic amine type developing agent, and at least one compound which is a solvent for the coupler.
- the coupler has the general formula:
- X is a coupler residue of the phenolic, pyrazolone or acetanilide type, R, is hydrogen or lower alkyl, R and R are individually hydrogen or alkyl (C to C R is hydrogen, or alkyl or alkoxy having 4-18 carbon atoms and n is 0 to 3.
- R is hydrogen
- R and R are alkyl groups and the total sum of the carbon atoms of R and R is 6 to 25.
- R is alkyl or alkoxy, R and R are both hydrogen.
- the solvent has the general formula:
- Coupler dispersions having improved stability are obtained.
- the present invention relates to a light-sensitive color photographic material. More particularly, the invention pertains to a light-sensitive color photographic material to which has been incorporated a novel combination of a coupler with a coupler solvent.
- the object of the present invention is to provide a lightsensitive color photographic material having excellent photographic properties which is entirely free from such drawbacks as mentioned above.
- We have found that the above object can be accomplished by using, as a component of a solvent for a coupler of the general Formula I, a compound of the general Formula II.
- Y is a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- R is a hydrogen atom or a lower alkyl group
- R and R are individually a hydrogen atom or an alkyl group having 1 to 18 carbon atoms
- R is a hydrogen atom or an alkyl or alkoxy group having 4 to 18 carbon atoms
- n is an integer of 0 to 3
- R and R are alkyl groups and the total sum of the carbon atoms of R and R is 6 to 25, and in case R is an alkyl or alkoxy group, both R and R are hydrogen atoms.
- the coupler can attain such prominent photographic properties that it is greatly prevented from crystallization and agglomeration and has excellent developability without any detrimental elfect on photographic emulsions and on dye images formed after development treatment.
- the couplers used in the present invention which are represented by the general Formula I, are preferably those which contain groups having carbon atoms within the aforesaid ranges, in order to prevent the diffusion thereof from layers, to which the couplers have been incorporated, to other layers.
- the coupler residue should be one capable of forming a dye by coupling with an oxidation product of a p-phenylenediamine type color developing agent.
- Typical examples of the couplers used in the present invention are as follows:
- coupler solvents e.g. water-immiscible m high boiling organic solvents such as dibutyl phthalate
- the amount of the compound represented by the general Formula II is ordinarily 0.02 to 3.0 parts per part of the coupler. However, the amount is not always limited to said range, and favorable results can be obtained by any combination of at least one coupler of the general Formula I with at least one compound of the general Formula II.
- a mixture of the coupler with the coupler solvent is dispersed in the form of finely divided liquid particles in a water-soluble or -permeable material such as gelatine, polyvinyl alcohol or other watersoluble synthetic resin, or in a light-sensitive silver halide emulsion containing said material as a binder.
- the coupler is first dissolved in the coupler solvent and then dispersed by way of a homogenizer or the like, the dispersion being stabilized, if necessary, with an emulsifier such as alkylbenzenesulfonate.
- the dispersion may be formed by dissolving the coupler and the coupler solvent in a low boiling organic solvent such as ethyl acetate and then dispersing the resulting solution in water or in a binder solution. At a later stage, the low boiling organic solvent may be removed, if necessary, by evaporation or washing.
- the dispersion is coated according to an ordinary procedure on a suitable support, followed by drying, whereby a light-sensitive color photographic material of the present invention can be obtained.
- the silver halide emulsion to be used in the present invention may be any of silver bromide, silver iodobromide, silver chloride, silver chlorobromide and the like silver halide emulsions, and the said emulsion and the aforesaid binder may have been incorporated with various photographic additives such as fog inhibitors, stabilizers, sensitizers, hardeners and the like.
- the amount thereof is preferably in the range of 1 to 300 g. per mole of the silver halide, and in case the coupler is to be added to other layer of a photographic material, the amount thereof is preferably in the range of 1 to 500 g. per g. of the binder, though the amount is variable depending on the purpose of application of the resulting photographic material.
- EXAMPLE 1 3 g. of 1-(2',4,6-trichlorophenyl)-3-[3"-(2"',4"-ditert amylphenoxyacetamide) benzamideJ-S-pyrazolone was dissolved in a mixture of 0.6 g. of 2,4-di-tert-amylphenoxyacetic acid, 0.9 g. of tricresyl phosphate and 9.0 g. of ethyl acetate by heating at 60 C. The resulting solution was poured into a mixture of 23 cc. of a 10% aqueous gelatine solution, 7 cc.
- a dispersion was prepared in the same manner as above, except that the 2,4-di-tert-amylphenoxyacetic acid was not used and the amount of the tricresyl phosphate was increased by 0.6 g.
- Ratio of solvent to coupler 1 Turbidity was measured using 0.2 mm. cell in a turbidimeter, Model SEP-PL, manufactured by Nippon Seimitsu Kogaku K.K.
- EXAMPLE 2 5 g. of m- ⁇ 3-[a-(2,4-di-tert-amylphenoxy) butylamide] benzoyl ⁇ -u- (4 nitrophenoxy) -2-methoxy-acetanilide was dissolved at about C. in a mixture comprising 2.5 g. of ethyl-a-(2,4-di-tert-amylphenoxy) propionate and 2.5 g. of dibutyl phthalate. The resulting solution was poured into a mixture of cc. of a 10% aqueous gelatine solution and 10 cc.
- a control sample was prepared in the same manner as above, except that the ethyl-a-(2,4-ditert-amylphenoxy) propionate was not used and the amount of the dibutyl phthalate was increased by 2.5 g.
- EXAMPLE 3 1.4 g. of 1-(2,4'-dimethyl-6'-chlorophenyl)-3-['y-(3"- n-pentadecylphenoxy)-butylamide]--pyrazolone and 0.6 g. of 1-(2',4'-dimethyl-6'-ch1orophenyl)-3-['y-(3"-n-pentadecylphenoxy)-butylamide] 4 (4"' methoxyphenylazo)-5-pyrazolone were dissolved at about 60 C. in a mixture comprising 0.6 g.
- a control sample was prepared in the same manner as above, except that the ethyl-'y-(3-n-pentadecylphenoxy) butylate was not used and the amount of the tricresyl phosphate was increased by 0.6 g.
- Turbidity was directly measured according to black board method using a turbidimeter, Model SEP-PL, manufactured by Nippon Seimltsu Kogaku K.K.
- a light-sensitive silver halide color photographic material which comprises finely divided liquid particles containing at least one coupler being capable of coupling with the oxidation product of a primary aromatic amine type developing agent and having the general Formula I: X-NHCO-(FH-(CHzh-OQ-Ri I l: I ia (I) wherein X is a coupler residue of the phenolic, pyrazolone or acetanilide type; R is a hydrogen atom or a lower alkyl group; R and R are individually a hydrogen atom or an alkyl group having 1 to 18 carbon atoms; R is a hydrogen atom or an alkyl or alkoxy group having 4 to 18 carbon atoms; and n is an integer of 0 to 3, provided that in case R is a hydrogen atom, R and R are alkyl groups and the total sum of the carbon atoms of R and R is 6 to 25, and in case R is an alkyl or alkoxy group, both R and R are hydrogen atoms
- Y is a hydrogen atom or an alkyl group having 1 to 8 carbon atoms; and R R R R and n are as defined above.
- a light-sensitive silver halide color photographic material comprising finely-divided liquid particles containing the coupler 1-(2',4',6'-trchlorophenyl)-3-[3"-(2,4"'-ditert-amyl phenoxy acetoamido)-benzamido]-5-pyrazolone and 2,4-di-tert-amy1 phenoxy acetic acid as a solvent therefor.
- a light-sensitive silver halide color photographic emulsion which comprises finely divided liquid particles containing at least one coupler being capable of coupling with the oxidation product of a primary aromatic amine type developing agent and having the general Formula I:
- X is a coupler residue of the phenolic, pyrazolone or acetanilide type; R is a hydrogen atom or a lower alkyl group; R and R are individually a hydrogen atom or an alkyl group having 1 to 18 carbon atoms; R is a hydrogen atom or an alkyl or alkoxy group having 4 to 18 carbon atoms; and n is an integer of 0 to 3, provided that in case R is a hydrogen atom, R and R are alkyl groups and the total sum of the carbon atoms of R and R is 6 to 25, and in case R is an alkyl or alkoxy group, both R and R are hydrogen atoms, and at least one compound being a solvent for said coupler and having the general Formula II:
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP44069946A JPS4840422B1 (enrdf_load_stackoverflow) | 1969-09-05 | 1969-09-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3700454A true US3700454A (en) | 1972-10-24 |
Family
ID=13417313
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US68533A Expired - Lifetime US3700454A (en) | 1969-09-05 | 1970-08-31 | Light-sensitive silver halide color photographic material containing couplers and coupler solvents |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3700454A (enrdf_load_stackoverflow) |
| JP (1) | JPS4840422B1 (enrdf_load_stackoverflow) |
| DE (1) | DE2043271C3 (enrdf_load_stackoverflow) |
| GB (1) | GB1285254A (enrdf_load_stackoverflow) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3772002A (en) * | 1971-10-14 | 1973-11-13 | Minnesota Mining & Mfg | Phenolic couplers |
| US3973979A (en) * | 1973-05-19 | 1976-08-10 | Agfa-Gevaert, A.G. | Color photographic materials containing diffusion fast pyrazolone couplers |
| US4146400A (en) * | 1976-09-09 | 1979-03-27 | Agfa-Gevaert Ag | Color photographic material containing new 2-equivalent yellow couplers |
| US5426019A (en) * | 1993-12-30 | 1995-06-20 | Eastman Kodak Company | Color photographic element |
| US5451497A (en) * | 1993-12-30 | 1995-09-19 | Eastman Kodak Company | Photographic dispersion having improved stability |
| WO2012014955A1 (ja) | 2010-07-30 | 2012-02-02 | 富士フイルム株式会社 | 新規なアゾ化合物、水溶液、インク組成物、インクジェット記録用インク、インクジェット記録方法、インクジェット記録用インクカートリッジ、及びインクジェット記録物 |
| WO2012014954A1 (ja) | 2010-07-30 | 2012-02-02 | 富士フイルム株式会社 | 新規なアゾ化合物、水溶液、インク組成物、インクジェット記録用インク、インクジェット記録方法、インクジェット記録用インクカートリッジ、及びインクジェット記録物 |
| EP2455431A1 (en) | 2003-10-23 | 2012-05-23 | Fujifilm Corporation | Ink and ink set for inkjet recording |
| EP2712894A1 (en) | 2012-09-26 | 2014-04-02 | Fujifilm Corporation | Azo compound, aqueous solution, ink composition, ink for inkjet recording, inkjet recording method, ink cartridge for inkjet recording, and inkjet recorded material |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9201235D0 (en) * | 1992-01-21 | 1992-03-11 | Kodak Ltd | Improvements in dye stability |
| US5605785A (en) * | 1995-03-28 | 1997-02-25 | Eastman Kodak Company | Annealing processes for nanocrystallization of amorphous dispersions |
-
1969
- 1969-09-05 JP JP44069946A patent/JPS4840422B1/ja active Pending
-
1970
- 1970-08-31 US US68533A patent/US3700454A/en not_active Expired - Lifetime
- 1970-09-01 DE DE2043271A patent/DE2043271C3/de not_active Expired
- 1970-09-04 GB GB42607/70A patent/GB1285254A/en not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3772002A (en) * | 1971-10-14 | 1973-11-13 | Minnesota Mining & Mfg | Phenolic couplers |
| US3973979A (en) * | 1973-05-19 | 1976-08-10 | Agfa-Gevaert, A.G. | Color photographic materials containing diffusion fast pyrazolone couplers |
| US4146400A (en) * | 1976-09-09 | 1979-03-27 | Agfa-Gevaert Ag | Color photographic material containing new 2-equivalent yellow couplers |
| US5426019A (en) * | 1993-12-30 | 1995-06-20 | Eastman Kodak Company | Color photographic element |
| US5451497A (en) * | 1993-12-30 | 1995-09-19 | Eastman Kodak Company | Photographic dispersion having improved stability |
| EP2455431A1 (en) | 2003-10-23 | 2012-05-23 | Fujifilm Corporation | Ink and ink set for inkjet recording |
| WO2012014955A1 (ja) | 2010-07-30 | 2012-02-02 | 富士フイルム株式会社 | 新規なアゾ化合物、水溶液、インク組成物、インクジェット記録用インク、インクジェット記録方法、インクジェット記録用インクカートリッジ、及びインクジェット記録物 |
| WO2012014954A1 (ja) | 2010-07-30 | 2012-02-02 | 富士フイルム株式会社 | 新規なアゾ化合物、水溶液、インク組成物、インクジェット記録用インク、インクジェット記録方法、インクジェット記録用インクカートリッジ、及びインクジェット記録物 |
| EP2712894A1 (en) | 2012-09-26 | 2014-04-02 | Fujifilm Corporation | Azo compound, aqueous solution, ink composition, ink for inkjet recording, inkjet recording method, ink cartridge for inkjet recording, and inkjet recorded material |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2043271B2 (de) | 1979-10-25 |
| DE2043271C3 (de) | 1980-07-17 |
| DE2043271A1 (de) | 1971-03-11 |
| GB1285254A (en) | 1972-08-16 |
| JPS4840422B1 (enrdf_load_stackoverflow) | 1973-11-30 |
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