US3582340A - Process for the antistatic treatment of light-sensitive silver halide photographic materials with phosphine oxide - Google Patents
Process for the antistatic treatment of light-sensitive silver halide photographic materials with phosphine oxide Download PDFInfo
- Publication number
- US3582340A US3582340A US741883A US3582340DA US3582340A US 3582340 A US3582340 A US 3582340A US 741883 A US741883 A US 741883A US 3582340D A US3582340D A US 3582340DA US 3582340 A US3582340 A US 3582340A
- Authority
- US
- United States
- Prior art keywords
- light
- silver halide
- halide photographic
- sensitive silver
- solution
- 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 abstract description 32
- -1 silver halide Chemical class 0.000 title abstract description 11
- 229910052709 silver Inorganic materials 0.000 title abstract description 10
- 239000004332 silver Substances 0.000 title abstract description 10
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 title abstract description 4
- 238000000034 method Methods 0.000 title description 10
- 230000000694 effects Effects 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 29
- 239000000243 solution Substances 0.000 description 29
- 230000003068 static effect Effects 0.000 description 15
- 239000010410 layer Substances 0.000 description 14
- 239000000839 emulsion Substances 0.000 description 9
- 239000011241 protective layer Substances 0.000 description 6
- 239000002216 antistatic agent Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000001828 Gelatine Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 230000001627 detrimental effect Effects 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000005299 abrasion Methods 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 description 1
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000006185 dispersion Substances 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
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920000728 polyester Polymers 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
- ZUNKMNLKJXRCDM-UHFFFAOYSA-N silver bromoiodide Chemical compound [Ag].IBr ZUNKMNLKJXRCDM-UHFFFAOYSA-N 0.000 description 1
- GDKIGKRYDCPBDU-UHFFFAOYSA-M sodium 4-(2-methyltetradecan-4-yloxy)-4-oxo-3-sulfobutanoate Chemical compound S(=O)(=O)(O)C(C(=O)OC(CC(C)C)CCCCCCCCCC)CC(=O)[O-].[Na+] GDKIGKRYDCPBDU-UHFFFAOYSA-M 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-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
- G03C1/85—Photosensitive materials characterised by the base or auxiliary layers characterised by antistatic additives or coatings
- G03C1/856—Phosphorus compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/167—X-ray
Definitions
- This invention relates to a process for the antistatic treatment of light-sensitive silver halide photographic materials, characterized by using phosphine oxides.
- drawbacks are brought about in such production steps as the step for coating of emulsion, the steps of cutting and packaging light-sensitive materials, and the like steps; in the case of taking sheet films from a box; in the case of taking pictures, particularly in filming; or in the case of handling of light-sensitive materials before development.
- Such drawbacks due to static charge are sometimes brought about also in the case of releasing of light-sensitive materials, in addition to the case of abrasion. That is, after emulsion-coating and drying, a light-sensitive material is rolled up, in general, and is then successively unrolled in order to transfer the material to subsequent step, or a rolled printing paper is successively released to be subjected to printing.
- antistatic agents in application of antistatic agents to light-sensitive photographic materials, it is a required condition that they should not have any detrimental efiect on photographic characteristics of the lightsensitive materials, such as speed, gradation, fog, stability, and the like. It is therefore extremely difficult to find excellent antistatic agents applicable to light-sensitive silver halide photographic materials.
- the above-mentioned compounds are incorporated into at least one layer of silver halide emulsion layer, subbing layer, inter layer, filter layer, anti-halation layer, protective layer and backing layer, it is possible to obtain light-sensitive silver halide photographic materials which are markedly less in drawbacks due to static charge. Further, the incorporation of the aforesaid compounds gives no detrimental elfect to the characteristics of light-sensitive photographic material, such as speed, gradation, fog, and the like.
- anionic surface active agents makes favorable the spreadability of photographic emulsions, in general, but disadvantageously increases the drawbacks due to static charge. Accordingly, it is impossible to select the kind of said agents only from the standpoint of spreadability.
- said agents are used in combination with the present compounds, the question of drawbacks due to static charge is solved, with the result that in the selection of anionic surface active agents, it becomes possible to give priority to the spreadability thereof.
- the phosphine oxides represented by the above-mentioned general formulas are synthesized, in general, either by reacting phosphorus hemitetraiodide with an alkyl iodide and then treating the reactor mixture with concentrated nitric acid, or by reacting phosphorus oxychloride, or a substituted phosphorus oxychloride in which the chlorine has been substituted by other substituent, with a Grignard reagent.
- the process for the synthesis thereof is disclosed in such literature as E. S. Levchenko, Y. V. Piren, A. B. Kilsanov: Zhurnal Obshchei Khimii, 1976-81 (1960), or G. M. Kosolapoff, R. F. Struck: Journal of the Chemical Society, 1959, 3950-2.
- the compounds may be used in the form of solutions in suitable solvents such as water or alcohols.
- suitable solvents such as water or alcohols.
- said solutions may be sprayed onto the surface of light-sensitive photographic materials, or light-sensitive materials may be immersed in said solutions.
- compounds poor in water solubility they may be incorporated after dissolving in solutions of suitable surface active agents less in influence on photographic emulsions, such as for example, anionic surface active agents, as mentioned before.
- the compounds of the present invention give favorable results even when incorporated into such treating solutions as developer, stopper, fixing solution and thickener, particularly into the thickener.
- the amounts of the present compounds to within the range of from about 0.1 mg. to about 1 g. per square meter of light-sensitive materials.
- EXAMPLE 1 The compound V was dissolved in water containing sodium dodecylbenzenesulfonate to form a 1% solution. The solution was sprayed onto the surface of a high speed X-ray film, and was then dried. On the other hand, the same X-ray films were immersed for 1 minute individually in the above-mentioned solution, and in a 1% sodi um dodecylbenzenesulfonate solution, and were then dried. These 3 treated films and an untreated X-ray film were allowed to stand for 24 hours under the conditions of a relative humidity of 30% and a temperature of 25 C.
- the surfaces of said films were abraded with nylon and polyester cloths, and then the films were developed, without exposure, according to an ordinary procedure using a developing solution for X-ray films.
- the generation of considerably marked static marks was observed, whereas in the films treated with the solution containing the compound V, no generation of static marks was observed.
- the films treated with the solution containing the compound V were subjected to sensitometry according to JIS procedure, but no influence on the films in speed, gradation and fog due to treatment with the solution containing the compound V was observed at all. Further, these films were stored for 3 days both in a thermostat at 55 C., and under the conditions of a temperature of 50 C. and a relative humidity of and were then subjected as well to sensitometry according to H8 procedure. In this case also, it was found that the compound V gave no influence to the films.
- EXAMPLE 2 The compound XIX was dissolved in a 4% solution of sodium decyl-isoamyl sulfosuccinate so that the concentration thereof became 2%. This solution 'was poured into a 2% gelatine solution, which was to be employed as a protective layer, in an amount of 20 cc. per liter of said gelatine solution. The mixed solution was applied as a protective layer onto the surface of a high speed X-ray film and was then dried. The resulting lightsensitive material was subjected to entirely the same test as in Example 1 together with the said X-ray film having the protective layer Which had not been incorporated with the compound XIX, whereby the same results as in Example 1 were obtained.
- EXAMPLE 3 10 cc. of a 5% methanol solution of the compound VIII was added to 1 l. of a green-sensitive silver iodobromide color-photographic emulsion. To the mixture was added a solution prepared by dissolving in a 1 N caustic soda solution 20 g. of the magenta coupler, 1-(4- phenoxy-3'-sulfophenyl)-3 heptadecyl pyrazolone, and then adjusting the resulting solution to pH 6.8 by means of citric acid. The thus obtained emulsion was applied onto a cellulose triacetate base and was then dried.
- the films were developed according to an ordinary procedure by use of a color developer composed mainly of diethyl-p-phenylenediamine, and were then subjected to the after-treatment.
- the generation of static marks was completely inhibited by incorporation of the compound VIII, but said compound gave no influence to photographic characteristics of the film, i.e. speed, gradation and fog.
- the compound VIII gave no detrimental effect.
- EXAMPLE 4 2 cc. of a 2% aqueous solution of the compound VI was added to a 5% aqueous gelatine solution containing an antihalation dye. To the mixed solution, 3 cc. of a 5% saponin solution was further added, and the mixture was applied onto the surface of a triacetate base and was then dried. Onto the reverse side of the base, a high speed photographic negative emulsion was applied, and as the protective layer thereon was applied a layer, into which 300 mg. per liter of the gelatine solution of the above-mentioned compound had been incorporated in the same manner as in Example 2. The resulting lightwherein R R and R individually represent an alkyl, aryl or aralkyl group and X is an alkylene group.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4332567 | 1967-07-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3582340A true US3582340A (en) | 1971-06-01 |
Family
ID=12660649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US741883A Expired - Lifetime US3582340A (en) | 1967-07-07 | 1968-07-02 | Process for the antistatic treatment of light-sensitive silver halide photographic materials with phosphine oxide |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3582340A (enrdf_load_stackoverflow) |
| DE (1) | DE1772806A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1225293A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3895951A (en) * | 1972-09-29 | 1975-07-22 | Agfa Gevaert Ag | Silver halide emulsion supersensitized with a merocyanine dye and a tertiary phosphine sulfide |
| US3954473A (en) * | 1974-06-24 | 1976-05-04 | Polaroid Corporation | Method of bleaching metallic silver |
-
1968
- 1968-07-02 US US741883A patent/US3582340A/en not_active Expired - Lifetime
- 1968-07-06 DE DE19681772806 patent/DE1772806A1/de active Pending
- 1968-07-08 GB GB1225293D patent/GB1225293A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3895951A (en) * | 1972-09-29 | 1975-07-22 | Agfa Gevaert Ag | Silver halide emulsion supersensitized with a merocyanine dye and a tertiary phosphine sulfide |
| US3954473A (en) * | 1974-06-24 | 1976-05-04 | Polaroid Corporation | Method of bleaching metallic silver |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1225293A (enrdf_load_stackoverflow) | 1971-03-17 |
| DE1772806A1 (de) | 1971-06-16 |
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