US3912515A - Silver halide photosensitive material - Google Patents
Silver halide photosensitive material Download PDFInfo
- Publication number
- US3912515A US3912515A US425977A US42597773A US3912515A US 3912515 A US3912515 A US 3912515A US 425977 A US425977 A US 425977A US 42597773 A US42597773 A US 42597773A US 3912515 A US3912515 A US 3912515A
- Authority
- US
- United States
- Prior art keywords
- benzene
- silver halide
- photosensitive material
- halide photosensitive
- solvent
- 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
- 239000000463 material Substances 0.000 title claims abstract description 18
- -1 Silver halide Chemical class 0.000 title claims abstract description 17
- 239000004332 silver Substances 0.000 title claims abstract description 11
- 229910052709 silver Inorganic materials 0.000 title claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 28
- 238000009835 boiling Methods 0.000 claims abstract description 16
- 239000000654 additive Substances 0.000 claims abstract description 14
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 claims description 8
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 claims description 8
- 239000006096 absorbing agent Substances 0.000 claims description 6
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 claims description 6
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 4
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 2
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 claims description 2
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 7
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 125000004104 aryloxy group Chemical group 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 3
- 239000001257 hydrogen Substances 0.000 abstract description 3
- 150000001924 cycloalkanes Chemical class 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 108010010803 Gelatin Proteins 0.000 description 10
- 229920000159 gelatin Polymers 0.000 description 10
- 239000008273 gelatin Substances 0.000 description 10
- 235000019322 gelatine Nutrition 0.000 description 10
- 235000011852 gelatine desserts Nutrition 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 8
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 5
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229960002380 dibutyl phthalate Drugs 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1 -dodecene Natural products CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- NGKNMHFWZMHABQ-UHFFFAOYSA-N 4-chloro-2h-benzotriazole Chemical compound ClC1=CC=CC2=NNN=C12 NGKNMHFWZMHABQ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 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
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/815—Photosensitive materials characterised by the base or auxiliary layers characterised by means for filtering or absorbing ultraviolet light, e.g. optical bleaching
-
- 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
- ABSTRACT An improved silver halide photosensitive material is disclosed which comprises, as a high boiling point solvent for photographic additives such as couplers, at least one solvent selected from (1) straight or cyclic alkanes having at least 9 carbon atoms, (2) straight or cyclic alkenes having at least 9 carbon atoms, and (3) compounds represented by the following general formula:
- R R and R are individually hydrogen, alkyl, cycloalkyl or aryloxy, or R and R can cooperatively form a hydrocarbon ring as members thereof.
- SILVER HALIDE PHOTOSENSITIVE MATERIAL consisting of (1) compounds represented by the gen eral formula
- This invention relates to a photographic material characterized in that a photographic additive which is E usually added to a photographic material in the form dissolved in a high boiling point solvent, such as a ultraviolet absorber, a coupler and the like, is incorporated 2 3 in a photographic material with use of a novel photographic solvent.
- ultraviolet absorbers of (wherein R R2 and R3 are respectively a hydrogen the behlophehohe yp the behzh'lazoletype1 the atom, alkyl, cycloalkyl, aryloxy, or R and R may form lohhrhe yp the trialihe type and of the cyahome' together a hydrocarbon ring,) (2) straight and cyclic thylehebehlodhhiol yp are employed as Ph alkanes having at least 9 carbon atoms and (3) straight g p ultravlolet absorbers and and cyclic alkenes having at least 9 carbon atoms.
- high boiling point solvents may be used singly or followmg formula in the form of a mixture of two or more of them, It is also possible to employ these high boiling point sol- OH vents in combination with low boiling point solvents as in 1the case of conventt iolpal hitglhbbciiling point slolvents.
- ypica instances 0 t e hig oi ing oint so vent to C0NH(CH) OT Q csHm be used in this invention include cum ne, p-cymene, mesitylene, di-isopropyl benzene, n-butyl benzene, seccsHum butyl benzene, t-butyl benzene, hexyl benzene, cyclo- 5 hexyl benzene, dodecyl benzene, diphenyl ether, n-
- decane decalin, tetralin, l-dodecene, l-decene, and
- TEST EXAMPLE fi O A mixture of four ultraviolet absorbers, 2-(2- hydroxy-S -tert-butylphenyl)benztriazole, 2-( 2 NHCOCHTOTQ'QHH) hydroxy-3'-tert-butyl-5'-di-tert-butylpenyl)benztiazole N and 2-( 2-hydroxy-3 5 -di-tert-butylphenyl)-5- l cHnm chlorobenztriazole was used as the ultraviolet absorber.
- additives are usually added to a photographic Table 1 material in the state dissolved in a high boiling point I solvent such as di-n-butyl phthalate, triphenyl phosg 'j g f g ffig phate, tri-ocresyl phosphate, monophenyl-di-p-tert- 50mm Absorber Began butyl phosphate, monophenyl di-o-chlorophenyl phosphate tri-p-tert-butylphenyl phosphate di-p'tert' g lTe h i dibutyl phthalate within 3 hours butylphenyl-mono-( 5-tert-butyl-2-phenyl-phenyl) Solvent of decalin more than I69 hours phosphate and the like.
- a high boiling point I solvent such as di-n-butyl phthalate, triphenyl phosg 'j g f g ffig phate,
- P F F P when a ultraviolet absorber is added to elemental sub- This invention is to provide a photographic material t stances of a photosensitive materlal in the form CllS- of good quality formed with use of a high boiling point 1 d th I t f d f solvent free of such defects involved in conventional 5 so m 6 so van 0 t l e F i high boiling point solvents ventional solvents as above mentioned are eliminated.
- the solvent to be used in this invention is photographically harmless and has no bad influences on other photographic additives.
- EXAMPLE 1 A photosensitive silver chlorobromide gelatin emulsion for red sensitive containing a cyan coupler was coated on a raw paper for photographic use, and a gelatin solution containing a solution of the same ultraviolet absorber as used in Test Example which was prepared with use of a high boiling point solvent indicated in Table 2 was coated on the emulsion layer so that a protective gelatin layer was formed at a base weight of 6.0 mg/ 10 cm Then, the coated gelatin layer was dried to obtain a test sample.
- the solution for formation of the gelatin protective layer was prepared by dissolving 3 g of the ultraviolet absorber in 6 ml of ethyl acetate and 3 ml of the high boiling point solvent, adding the solution to 60 ml of a 10% aqueous solution of gelatin containing saponin,
- the so obtained sample was exposed to light, subjected to color development, hardening fixation, bleaching fixation and water washing, and then dried.
- the red density of the cyan image and stain density (determined based on the blue color concentration) at non-image areas were measured. Then, the sample was exposed directly to 40 sun-light for hours while employing a blue scale as a comparison, and the red density and stain density were measured again. Results of the reduction ratio of the red density and the stain density are shown in Table Table 2 Reduction Ratio of Red Color Density (density Stain Density As is seen from the results shown in Table l, the protective gelatin layer containing a solvent according to this invention exhibits fading preventive effect and stain preventive effect substantially equal to these of a gelatin protective layer containing a solvent of difutyl phthalate.
- the solution comprising photographic additives and the solvent according to this invention exhibited more stability than the solution comprising photographic additives and the dibutyl phthalate, that is, crystalization did not occured on and before coating at all.
- ultraviolet absorber 4,7- bis(,B-ethoxyethoxy corbonylmethoxy)-2- dicyanomethylene-l,3-benzodithiole was used instead of a mixture of four kinds of benztriazole, supreme results are also obtained as same as the above.
- EXAMPLE 2 v 20 mg of l-(2,4,6-trichlorophenyl)-3-[-3- ⁇ (2,4-ditert-amylphenoxy)-acetamidelbenzamide1-5- pyrazolone was dissolved in 20 ml of l-nonene and ml of ethyl acetate (maintained at 60C), and the-solution was mixed with 10 ml of a 10% aqueous solution of Alkanol B and 200 m of a 5 aqueous solution of gelatin. The mixture was emulsified and dispersed by means of a colloid mill.
- the so obtained dispersion was added to 1 Kg of a.'silver chlorobromide emulsion for formation of photographic papers, and the mixture was coated on a raw papers, and dried.
- the so obtained sample was exposed to green light exposure, subjected to color development hardening fixation, bleaching fixation and water washing, and dried.
- an image of a magenta color comparable to the image obtained by employing dibutyl phthalate instead of lnonene.
- a silver halide photosensitive material comprising a high boiling point solvent for photographic additives, the improvement which comprises said solvent being selected from a group consisting of straight or cyclic, alkanes and alkenes having at least 9 carbon atoms; and cumene, p-cymene, mesitylene, diisopropyl benzene, n-butyl benzene, sec-butyl benzene, t-butyl benzene, hexyl benzene, cyclohexyl benzene, dodecyl benzene and dephenyl ether.
- solvent being selected from a group consisting of straight or cyclic, alkanes and alkenes having at least 9 carbon atoms; and cumene, p-cymene, mesitylene, diisopropyl benzene, n-butyl benzene, sec-butyl benzene, t-butyl
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13025872A JPS561615B2 (enrdf_load_stackoverflow) | 1972-12-28 | 1972-12-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3912515A true US3912515A (en) | 1975-10-14 |
Family
ID=15029943
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US425977A Expired - Lifetime US3912515A (en) | 1972-12-28 | 1973-12-19 | Silver halide photosensitive material |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3912515A (enrdf_load_stackoverflow) |
| JP (1) | JPS561615B2 (enrdf_load_stackoverflow) |
| DE (1) | DE2364040A1 (enrdf_load_stackoverflow) |
| GB (2) | GB1452319A (enrdf_load_stackoverflow) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4839267A (en) * | 1986-11-21 | 1989-06-13 | Agfa-Gevaert, N.V. | Colour photographic motion picture element |
| 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 |
| 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 |
| 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 (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5313414A (en) * | 1976-07-23 | 1978-02-07 | Mitsubishi Paper Mills Ltd | Improved silver halide color photographic photosensitive material |
| JPS59133545A (ja) * | 1983-01-19 | 1984-07-31 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀写真感光材料 |
| JPS6134538A (ja) * | 1984-07-26 | 1986-02-18 | Fuji Photo Film Co Ltd | ハロゲン化銀写真感光材料及びその製造方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3658546A (en) * | 1969-03-20 | 1972-04-25 | Agfa Gevaert Nv | Method of incorporating photographic ingredients into photographic colloid compositions |
| US3676142A (en) * | 1968-09-10 | 1972-07-11 | Agfa Gevaert | Method of incorporating photographic ingredients into photographic colloid compositions |
| US3752672A (en) * | 1967-10-11 | 1973-08-14 | Agfa Gevaert Nv | Method of incorporating ingredients in hydrophilic colloids |
| US3788857A (en) * | 1970-08-13 | 1974-01-29 | Agfa Gevaert Nv | Method of incorporating photographic adjuvants into hydrophilic colloids |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1077426A (en) * | 1965-03-30 | 1967-07-26 | Ilford Ltd | Production of colour photographic materials |
-
1972
- 1972-12-28 JP JP13025872A patent/JPS561615B2/ja not_active Expired
-
1973
- 1973-12-19 GB GB5886573A patent/GB1452319A/en not_active Expired
- 1973-12-19 US US425977A patent/US3912515A/en not_active Expired - Lifetime
- 1973-12-19 GB GB1546376A patent/GB1452320A/en not_active Expired
- 1973-12-21 DE DE2364040A patent/DE2364040A1/de active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3752672A (en) * | 1967-10-11 | 1973-08-14 | Agfa Gevaert Nv | Method of incorporating ingredients in hydrophilic colloids |
| US3676142A (en) * | 1968-09-10 | 1972-07-11 | Agfa Gevaert | Method of incorporating photographic ingredients into photographic colloid compositions |
| US3658546A (en) * | 1969-03-20 | 1972-04-25 | Agfa Gevaert Nv | Method of incorporating photographic ingredients into photographic colloid compositions |
| US3788857A (en) * | 1970-08-13 | 1974-01-29 | Agfa Gevaert Nv | Method of incorporating photographic adjuvants into hydrophilic colloids |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4839267A (en) * | 1986-11-21 | 1989-06-13 | Agfa-Gevaert, N.V. | Colour photographic motion picture element |
| EP2455431A1 (en) | 2003-10-23 | 2012-05-23 | Fujifilm Corporation | Ink and ink set for inkjet recording |
| 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 |
| 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 |
| 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 |
|---|---|
| JPS561615B2 (enrdf_load_stackoverflow) | 1981-01-14 |
| DE2364040A1 (de) | 1974-07-04 |
| GB1452320A (en) | 1976-10-13 |
| JPS4990523A (enrdf_load_stackoverflow) | 1974-08-29 |
| GB1452319A (en) | 1976-10-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: KONICA CORPORATION, JAPAN Free format text: RELEASED BY SECURED PARTY;ASSIGNOR:KONISAIROKU PHOTO INDUSTRY CO., LTD.;REEL/FRAME:005159/0302 Effective date: 19871021 |