US3725077A - Silver halide emulsions stabilized with nitroso derivatives of phenols - Google Patents
Silver halide emulsions stabilized with nitroso derivatives of phenols Download PDFInfo
- Publication number
- US3725077A US3725077A US00138292A US3725077DA US3725077A US 3725077 A US3725077 A US 3725077A US 00138292 A US00138292 A US 00138292A US 3725077D A US3725077D A US 3725077DA US 3725077 A US3725077 A US 3725077A
- Authority
- US
- United States
- Prior art keywords
- silver halide
- prepared according
- fog
- assay
- halide emulsions
- 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
- 239000000839 emulsion Substances 0.000 title abstract description 19
- -1 Silver halide Chemical class 0.000 title abstract description 14
- 229910052709 silver Inorganic materials 0.000 title abstract description 10
- 239000004332 silver Substances 0.000 title abstract description 10
- 150000002832 nitroso derivatives Chemical class 0.000 title 1
- 150000002989 phenols Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract description 9
- 230000006641 stabilisation Effects 0.000 abstract description 6
- 238000011105 stabilization Methods 0.000 abstract description 6
- 229910052736 halogen Inorganic materials 0.000 abstract description 4
- 150000002367 halogens Chemical class 0.000 abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- 238000003556 assay Methods 0.000 description 13
- 239000010410 layer Substances 0.000 description 9
- 229920000728 polyester Polymers 0.000 description 8
- 239000003381 stabilizer Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- JSTCPNFNKICNNO-UHFFFAOYSA-N 4-nitrosophenol Chemical compound OC1=CC=C(N=O)C=C1 JSTCPNFNKICNNO-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 238000005266 casting Methods 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- DZCCLNYLUGNUKQ-UHFFFAOYSA-N n-(4-nitrosophenyl)hydroxylamine Chemical compound ONC1=CC=C(N=O)C=C1 DZCCLNYLUGNUKQ-UHFFFAOYSA-N 0.000 description 4
- DZOWQEYGMAQVGM-UHFFFAOYSA-N 3-chloro-2-nitrosophenol Chemical compound ClC=1C(=C(C=CC1)O)N=O DZOWQEYGMAQVGM-UHFFFAOYSA-N 0.000 description 3
- 101710134784 Agnoprotein Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VTWDKFNVVLAELH-UHFFFAOYSA-N 2-methylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C=CC1=O VTWDKFNVVLAELH-UHFFFAOYSA-N 0.000 description 2
- LCPQHPZPSPNDSA-UHFFFAOYSA-N 3-chloro-4-nitrosophenol Chemical compound OC1=CC=C(N=O)C(Cl)=C1 LCPQHPZPSPNDSA-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 2
- WOAHJDHKFWSLKE-UHFFFAOYSA-N 1,2-benzoquinone Chemical compound O=C1C=CC=CC1=O WOAHJDHKFWSLKE-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- MITIGYREXOUULB-UHFFFAOYSA-N 2-bromo-3,5-dimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=CC(=O)C(Br)=C(C)C1=O MITIGYREXOUULB-UHFFFAOYSA-N 0.000 description 1
- WOGWYSWDBYCVDY-UHFFFAOYSA-N 2-chlorocyclohexa-2,5-diene-1,4-dione Chemical compound ClC1=CC(=O)C=CC1=O WOGWYSWDBYCVDY-UHFFFAOYSA-N 0.000 description 1
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 1
- ZVNPWFOVUDMGRP-UHFFFAOYSA-N 4-methylaminophenol sulfate Chemical compound OS(O)(=O)=O.CNC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1 ZVNPWFOVUDMGRP-UHFFFAOYSA-N 0.000 description 1
- INVVMIXYILXINW-UHFFFAOYSA-N 5-methyl-1h-[1,2,4]triazolo[1,5-a]pyrimidin-7-one Chemical compound CC1=CC(=O)N2NC=NC2=N1 INVVMIXYILXINW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 108010010803 Gelatin Proteins 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
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000012790 adhesive layer Substances 0.000 description 1
- LAABTJXWUKMZIV-UHFFFAOYSA-N benzene-1,4-diol;4-(methylamino)phenol Chemical compound OC1=CC=C(O)C=C1.CNC1=CC=C(O)C=C1 LAABTJXWUKMZIV-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 230000002925 chemical effect Effects 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- JVXNCJLLOUQYBF-UHFFFAOYSA-N cyclohex-4-ene-1,3-dione Chemical compound O=C1CC=CC(=O)C1 JVXNCJLLOUQYBF-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 229940035423 ethyl ether Drugs 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000002344 gold compounds Chemical class 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000080 wetting agent 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
- G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
Definitions
- the present invention relates to a process for the stabilizing of photographic silver halide emulsions.
- the silver halide of photographic layers may also be developed without exposure; this den sity is generally called a fog.
- fog can thus result in photographic materials by excessively long storage, by storage at excessively high temperatures and moistures; furthermore, fog may result due to high pressure, this is termed pressure fog.
- chemical effects such as impurities of polyester material, precipitates from interleaving paper, the synthetic polymers, for example, polyvinylidene chloride polymer, used for the intermediate layer and adhesive layer, especially with respect to a polyester base, and atmospheric impurities often bring about fog.
- This disturbing fog is often accompanied by other factors which disadvantageously influence the quality of the photographic layer.
- These disadvantages include contrast and sensitivity instabilities, usually one contrast measure and one sensitivity measure loss because of the fog formation proceeding.
- Another object is providing a stabilization method which assures fog-free storage specimens and eliminates disadvantages of the previously known stabilization methods or surpasses their effectiveness.
- the elfect of the new stabilizers is not limited only to the casting of the emulsion on a triacetate base but instead stands out even more prominently with respect to casting the emulsion on a usually more extensively fogging polyester base.
- 3-chloro-4-nitrosophenol or 3-chloro-4-monoxime quinone may be prepared as follows: 10 g. NaOH (1 mol +5 excess) are dissolved while stirring in 500 ml. H O; 25.7 g. m-chlorophenol (1 mol) and 13.8 g. NaNO (1 mol) are added one after the other while stirring. Cooled to 2 C. with a sodium chloride-ice mixture. Slowly added in drops 20 g. (10.8 ml.) concentrated H (1 mol) thinned with ml. H O. Restirred for 1 hour; allowed to stand overnight. The separated oil taken up in benzene; drawn off from the undissolved. The substance obtained from the benzene solution is already pure. F. C. (decomposition).
- novel compounds may also be added to a layer adjacent to the emulsion layer; these compounds may equally be added separately in the substratum, foundation or superstratum and protective layer, respectively.
- silver halide layers are spectrally sensitized or treated With a chemical sensitizer known from patents or literature.
- these novel compounds may be combined also with the stabilizers known from literature and patents, such as triazaindolizine, mercapto compounds, Hg and Au compounds, etc.
- the use of the novel compounds together with 1,3,4-triazandolizine, as descrbied by the fundamental article of Birr, Z. wiss. Phot. 1952, p. 2-27 is particularly effective with reference to the contrast stabilization.
- color components and other well known additives for photographic silver halide emulsions are employed according to the invention together with the antifogging agents.
- concentrations employed in the sense of the invention are generally l300 mg. per 100 g. AgNO
- concentrations employed in the sense of the invention are generally l300 mg. per 100 g. AgNO
- the invention is explained in more detail by way of example:
- EXAMPLE 1 A silver chlorobromide emulsion with approximately 20% mol bromide freed of the excess salts by coagulation procedure, which normally is used for line and halftone reproduction purposes, is digested in the presence of a stabilizer up to the sensitivity and contrast maxima.
- the emulsion is divided into three parts, the one part remains without additive, the second part is mixed with 200 mg. 7-hydroxy-5-methyl-1,3,4-triazaindolizine per 100 g. AgNO the third part is mixed with 40 mg. nitrosophenol per 100 AgNO Beside the uniform amounts of wetting agent, all three parts contain the same amount of gelatin hardening agent and softening agent.
- sensitometric strips are then cast onto a film base consisting of triacetate and polyester, dried, out into sensitometric strips. the one half stored for 72 hours at 60 C., the other part remaining without this thermal aftertreatment.
- the sensitometric strips are then exposed behind a stepped photometric absorption wedge and jointly developed for 3 minutes in a strongly alkaline p-methylaminophenol hydroquinone developer of the following composition: 1,000 ml. H 0, 2 g. p-methylaminophenol sulfate, 50 g. Na SO sic., 120 g. hydroquinone, 5 g. potassium bromide.
- quinone dioxime are added to the emulsion in place of nitrosophenol.
- a light-sensitive photographic element having on a support at least one silver halide emulsion layer which contains in a stabilizing amount of 0.01 to 0.3 grams per 100 grams of silver nitrate, a stabilizer having the following formula:
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2020943A DE2020943C3 (de) | 1970-04-29 | 1970-04-29 | Photographisches silberhalogenidhaltiges Aufzeichnungsmaterial |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3725077A true US3725077A (en) | 1973-04-03 |
Family
ID=5769746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00138292A Expired - Lifetime US3725077A (en) | 1970-04-29 | 1971-04-28 | Silver halide emulsions stabilized with nitroso derivatives of phenols |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3725077A (show.php) |
| BE (1) | BE766316A (show.php) |
| DE (1) | DE2020943C3 (show.php) |
| FR (1) | FR2090962A5 (show.php) |
| GB (1) | GB1311263A (show.php) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4357419A (en) * | 1981-04-02 | 1982-11-02 | Minnesota Mining And Manufacturing Company | Covering power in films |
| US4430426A (en) | 1982-06-04 | 1984-02-07 | Minnesota Mining And Manufacturing Company | Stabilization of silver halide emulsions |
| US5547827A (en) * | 1994-12-22 | 1996-08-20 | Eastman Kodak Company | Iodochloride emulsions containing quinones having high sensitivity and low fog |
-
1970
- 1970-04-29 DE DE2020943A patent/DE2020943C3/de not_active Expired
-
1971
- 1971-04-26 GB GB1126971*[A patent/GB1311263A/en not_active Expired
- 1971-04-27 BE BE766316A patent/BE766316A/nl unknown
- 1971-04-28 US US00138292A patent/US3725077A/en not_active Expired - Lifetime
- 1971-04-29 FR FR7115444A patent/FR2090962A5/fr not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4357419A (en) * | 1981-04-02 | 1982-11-02 | Minnesota Mining And Manufacturing Company | Covering power in films |
| US4430426A (en) | 1982-06-04 | 1984-02-07 | Minnesota Mining And Manufacturing Company | Stabilization of silver halide emulsions |
| US5547827A (en) * | 1994-12-22 | 1996-08-20 | Eastman Kodak Company | Iodochloride emulsions containing quinones having high sensitivity and low fog |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2020943C3 (de) | 1979-10-18 |
| GB1311263A (en) | 1973-03-28 |
| BE766316A (nl) | 1971-10-27 |
| DE2020943A1 (de) | 1971-11-18 |
| FR2090962A5 (show.php) | 1972-01-14 |
| DE2020943B2 (de) | 1979-02-15 |
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