US3545974A - Method for preparing photographic light-sensitive elements - Google Patents
Method for preparing photographic light-sensitive elements Download PDFInfo
- Publication number
- US3545974A US3545974A US714020A US3545974DA US3545974A US 3545974 A US3545974 A US 3545974A US 714020 A US714020 A US 714020A US 3545974D A US3545974D A US 3545974DA US 3545974 A US3545974 A US 3545974A
- Authority
- US
- United States
- Prior art keywords
- surface active
- compound
- active agent
- photographic
- photographic light
- 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
- 238000000034 method Methods 0.000 title description 10
- 239000004094 surface-active agent Substances 0.000 description 28
- 239000000839 emulsion Substances 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 19
- 239000008199 coating composition Substances 0.000 description 16
- 229910052709 silver Inorganic materials 0.000 description 14
- 239000004332 silver Substances 0.000 description 14
- -1 silver halide Chemical class 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 11
- 238000000576 coating method Methods 0.000 description 11
- 108010010803 Gelatin Proteins 0.000 description 8
- 229920000159 gelatin Polymers 0.000 description 8
- 239000008273 gelatin Substances 0.000 description 8
- 235000019322 gelatine Nutrition 0.000 description 8
- 235000011852 gelatine desserts Nutrition 0.000 description 8
- 239000000203 mixture Substances 0.000 description 5
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000005562 fading Methods 0.000 description 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 3
- 229920002284 Cellulose triacetate Polymers 0.000 description 3
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000004061 bleaching Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
- ZGPNPGCCMJXNKN-UHFFFAOYSA-N aminophosphonous acid ethene Chemical compound C=C.C=C.C=C.P(N)(O)O ZGPNPGCCMJXNKN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 230000002939 deleterious effect Effects 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- BWLAEMGERUUFFR-UHFFFAOYSA-N 4-n,4-n,2-trimethylbenzene-1,4-diamine;hydrochloride Chemical compound Cl.CN(C)C1=CC=C(N)C(C)=C1 BWLAEMGERUUFFR-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- LRLGWNCIMXNNHM-UHFFFAOYSA-N C(CCCCCCCCCCC)OS(=O)C1=CC=CC=C1.[Na] Chemical compound C(CCCCCCCCCCC)OS(=O)C1=CC=CC=C1.[Na] LRLGWNCIMXNNHM-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241001466767 Galathea perone Species 0.000 description 1
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000000463 material 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
- 239000004533 oil dispersion Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001043 yellow dye 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
- G03C1/00—Photosensitive materials
- G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
- G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
- G03C1/38—Dispersants; Agents facilitating spreading
Definitions
- the present invention relates generally to a method for preparing light-sensitive elements and more particua surface active agent thus incorporated does not reduce the photographic properties of the photographic light-sensitive element not reduce the speed of forming the color images on developing the photographic light-sensitive element.
- R-I- R'o rr 011260 wherein R represents an alkyl group having more than 6 carbon atoms, R represents ethylene or propylene, and p+q is a positive integer larger than 5, excellent for improving the coating properties of the coating composition, is inadequate for color photography since it diminishes the clarity of the colors and it accelerates the fading of the color image due to heat and moisture exposure thereby reducing the life or stability of the color photograph. It is believed that the deleterious results are caused by the bleaching or silver-removing power of the surface active agent by oxidation during the developing process.
- an aqueous emulsified dispersion of the coupler is prepared with an oily material and an anionic surface active agent which is added to the photographic silver halide emulsion.
- an anionic surface active agent shown by the general Formula A mentioned above is incorporated into the photographic silver halide emulsion, the
- colloidal stability of the dispersed coupler is reduced, causing aggregation of the coupler during developing and reduction in transparency of the emulsion layers after developing.
- an object of the present invention is to provide an amphoteric surface active agent in a photographic coating composition for improving the coating properties thereof without the aforesaid disadvantages.
- Another object of this invention is to provide a method for preparing a photographic light-sensitive element, in particular, a color photographic light-sensitive element, by employing the aforesaid amphoteric surface active agent for improving the coating property of the photographic coating composition without reducing either the photographic properties of the light-sensitive element or the fastness of the color images.
- the synthesis (i) mentioned above may be conducted by the method described in Kogyo Kagaku Zasshi (Journal of Industrial Chemistry); vol. 63, 595-600 (1960), and the synthesis (ii) may be conducted by the method described in Kogyo Kagaku Zasshi; vol. 60, 909 (1957).
- the compound represented by the aforesaid general Formula B may be incorporated in any coating composition of a photographic light-sensitive element but is more suitably incorporated into a photographic silver halide emulsion. It is particularly suitable for photographic silver halide emulsions in which the second ripening has been finished immediately before coating. Furthermore, the novel surface active agent of this invention, if desired, may be used together with other conventional surface active agents.
- amphoteric surface active agent is varied in accordance with various conditions, such as the type of coating composition, the manner of coating and the like, but in general the addition of 0.01- 0.2% by weight of the surface active agent based on the weight of the coating composition gives the best effect. This amount corresponds to 0.1-2.0 g. per one kg. of gelatin in the coating composition.
- a photographic emulsion containing the aforesaid surface active agent can be uniformly applied to a support with a high speed without deleterious effect on the photographic properties of the light-sensitive element.
- color images having good fastness can be obtained after developing the color photographic light-sensitive element containing the surface active agent of this invention.
- amphoteric surface active agent used in this invention causes few undesirable reactions with other additives of the emulsion, difficulties otherwise encountered during production of photographic light-sensitive elements are reduced.
- Example 1 An emulsifier dispersion prepared by dispersing a solution of 2.3 g. of a cyan coupler having the following in 5.0 ml. of tri-ortho-cresylphosphate ester in 40 ml. of an aqueous gelatin solution containing 0.2 g. of sodium n-dodecylbenzene sulfinate was added to 100 g. of a red-sensitive photographic emulsion containing 7 g. of gelatin and 5 g. of silver chlorobromide.
- the colored samples thus obtained were subjected to the following fading tests: (A) the sample was maintained for days under the conditions of 60 C. and 75% relative humidity; and (B) the sample was maintained for four hours at 120 C.
- the results are shown in the following table in which the initial optical density of the cyancolored image was 2.0.
- Example 2 Into a red-sensitive emulsion containing the coupler as shown in Example 1 were added 2.0 ml. of a 1% solution of each of Compounds I, II, III, and V, and 2.0 ml. of a 1% solution of a surface active agent having the following formula The coating composition thus prepared was applied to a triacetyl cellulose film at C. and set at 5 C. To the thus coated wet emulsion layer a coating composition prepared by adding 2 ml. of a 1% solution of a surface active agent, n-dodecylbenzene sulfonate, to 100 g. of a 2% gelatin solution was applied with various coating speeds.
- a coating composition prepared by adding 2 ml. of a 1% solution of a surface active agent, n-dodecylbenzene sulfonate, to 100 g. of a 2% gelatin solution was applied with various coating speeds.
- the colloidal stability of the coupler-containing the emulsified dispersion was signifivantly better than the conventional compound V. Further, the emulsion layer formed by the present invention has good transparency.
- Example 4 An emulsified dispersion prepared by dispersing a solution of 2.0 g. of a yellow coupler having the formula:
- Each of the emulsion samples thus prepared was mixed with 5 ml. of a 1% solution of compound I, II or V and 3 ml. of a 3% acetate solution of triethylene phosphorous amide, and the mixture was applied to a triacetyl cellulose film followed by drying to provide a light-sensitive film.
- the light-sensitive film was then blue-exposed stepwise and processed as in Example 1 to provide a yellow image.
- the blue density D and red density D of the image were measured, the results of which are shown in the following table.
- the blue density D shows the relative strength of yellow coupling and the red density D shows the relative density of a silver image remaining after processing.
- a photographic coating composition comprising a gelatin containing silver halide emulsion and a minor amount of a surface active agent having the formula:
- tive agent is present in an amount of 0.0 10.2% by weight based on the weight of the coating composition.
- composition of claim 1 wherein said silver halide is silver ehlorobromide.
- composition of claim 1 wherein said silver halide is silver iodobromide.
- composition of claim 7 wherein said coupling agent is a cyan coupler having the formula:
- a photographic element comprising a support having applied thereto a photographic coating compositioncomprising a gelatin containing silver halide emulsion and a minor amount of a surface active agent having the formula:
- R is an alkyl group having 8-20 carbon atoms and p and q of each represent positive integers.
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (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 |
|---|---|---|---|
| JP1679067 | 1967-03-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3545974A true US3545974A (en) | 1970-12-08 |
Family
ID=11925955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US714020A Expired - Lifetime US3545974A (en) | 1967-03-17 | 1968-03-18 | Method for preparing photographic light-sensitive elements |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3545974A (da) |
| BE (1) | BE712297A (da) |
| DE (1) | DE1622934C3 (da) |
| FR (1) | FR1557345A (da) |
| GB (1) | GB1164095A (da) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0124795A2 (en) | 1983-04-11 | 1984-11-14 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsion |
| US5155007A (en) * | 1990-03-30 | 1992-10-13 | Konica Corporation | Silver halide photographic material |
| US6071688A (en) * | 1998-07-29 | 2000-06-06 | Eastman Kodak Company | Providing additives to a coating composition by vaporization |
| US7250202B1 (en) | 1998-06-18 | 2007-07-31 | Ilford Imaging Ch Gmbh | Recording sheets for ink jet printing |
| WO2012035314A1 (en) | 2010-09-17 | 2012-03-22 | Fujifilm Manufacturing Europe Bv | Photographic paper |
| WO2021213762A1 (en) | 2020-04-24 | 2021-10-28 | Fujifilm Manufacturing Europe Bv | Photographic paper |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2140572B (en) * | 1983-05-26 | 1986-06-18 | Kodak Ltd | Photographic dispersions |
| US4990431A (en) * | 1989-01-17 | 1991-02-05 | Eastman Kodak Company | Methods of forming stable dispersions of photographic materials |
| US5158863A (en) * | 1989-01-17 | 1992-10-27 | Eastman Kodak Company | Methods of forming stable dispersions of photographic materials |
| IT1232339B (it) * | 1989-09-25 | 1992-01-28 | Minnesota Mining & Mfg | Elementi fotografici multistrato aventi una migliorata qualita' di stesa. |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3441413A (en) * | 1964-07-07 | 1969-04-29 | Fuji Photo Film Co Ltd | Photographic elements having gelatinous coating compositions containing amphoteric surface active agents |
-
1968
- 1968-03-15 BE BE712297D patent/BE712297A/xx unknown
- 1968-03-18 DE DE1622934A patent/DE1622934C3/de not_active Expired
- 1968-03-18 FR FR1557345D patent/FR1557345A/fr not_active Expired
- 1968-03-18 US US714020A patent/US3545974A/en not_active Expired - Lifetime
- 1968-03-18 GB GB02939/68A patent/GB1164095A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3441413A (en) * | 1964-07-07 | 1969-04-29 | Fuji Photo Film Co Ltd | Photographic elements having gelatinous coating compositions containing amphoteric surface active agents |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0124795A2 (en) | 1983-04-11 | 1984-11-14 | Fuji Photo Film Co., Ltd. | Silver halide photographic emulsion |
| US5155007A (en) * | 1990-03-30 | 1992-10-13 | Konica Corporation | Silver halide photographic material |
| US7250202B1 (en) | 1998-06-18 | 2007-07-31 | Ilford Imaging Ch Gmbh | Recording sheets for ink jet printing |
| US6071688A (en) * | 1998-07-29 | 2000-06-06 | Eastman Kodak Company | Providing additives to a coating composition by vaporization |
| WO2012035314A1 (en) | 2010-09-17 | 2012-03-22 | Fujifilm Manufacturing Europe Bv | Photographic paper |
| WO2021213762A1 (en) | 2020-04-24 | 2021-10-28 | Fujifilm Manufacturing Europe Bv | Photographic paper |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1622934C3 (de) | 1974-02-07 |
| FR1557345A (da) | 1969-02-14 |
| GB1164095A (en) | 1969-09-10 |
| DE1622934B2 (de) | 1973-07-19 |
| DE1622934A1 (de) | 1971-11-18 |
| BE712297A (da) | 1968-07-15 |
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