US2461987A - Antiplumming agents for photographic emulsions - Google Patents
Antiplumming agents for photographic emulsions Download PDFInfo
- Publication number
- US2461987A US2461987A US755718A US75571847A US2461987A US 2461987 A US2461987 A US 2461987A US 755718 A US755718 A US 755718A US 75571847 A US75571847 A US 75571847A US 2461987 A US2461987 A US 2461987A
- Authority
- US
- United States
- Prior art keywords
- plumming
- emulsion
- agents
- compound
- glazing
- 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 description 26
- 150000001875 compounds Chemical class 0.000 description 25
- 239000003795 chemical substances by application Substances 0.000 description 12
- 229910052709 silver Inorganic materials 0.000 description 12
- 239000004332 silver Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 150000004820 halides Chemical class 0.000 description 9
- 125000005843 halogen group Chemical group 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 125000000217 alkyl group Chemical group 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- -1 silver halide Chemical class 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- SWXXKWPYNMZFTE-UHFFFAOYSA-N (c-ethylsulfanylcarbonimidoyl)azanium;bromide Chemical compound Br.CCSC(N)=N SWXXKWPYNMZFTE-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- 229910021607 Silver chloride Inorganic materials 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
- JJMRJPAPJCFDAM-UHFFFAOYSA-N 2-chloro-n-pyridin-2-ylacetamide Chemical compound ClCC(=O)NC1=CC=CC=N1 JJMRJPAPJCFDAM-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000005406 washing Methods 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
- G03C1/35—Antiplumming agents, i.e. antibronzing agents; Toners
- G03C1/355—Organic derivatives of bivalent sulfur, selenium or tellurium
-
- 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
- Y10S430/13—Antibronze agent or process
Definitions
- This invention relates to anti-plumming agents for photographic materials and to a method of preventing plumming and bronzing of the developed images given by photographic silver halide emulsion, especially emulsions in which the halide is partly or wholly chloride.
- an object of our invention to provide photographic materials containing antiplumming agents.
- a further object is to provide a method of preventng plumming and bronzing during the hot-glazing of photographic prints.
- R represents an alkyl group and X represents a halogen atom.
- Our invention also provides a method of preventing plumming and bronzing during the hot-glazing of photographic prints which comprises developing a gelatinosilver halide emulsion'on which the prints are made in the presence of the compound represented by the above-mentioned formula.
- R represents an amide-substituted alkyl group, i.e., an alkyl group containing the groups NH2.CO-, whilst those in which the nitrogen atom of the said amido group carries a nitrogen-containing heterocyclic residue are preferred; for example, compounds of the type which are specially advantageous are those represented by the formula:
- X again represents a halogen atom and Y represents a member selected from the group consisting of pyriclyl, quinolyl, thiazyl, benzthiazyl, pyrimidyl, etc.
- the compounds of our invention are added, preferably to the emulsion layer or layers but they are also effective, when of the requisite solubility, if added to the developing or processing solutions or to other layers carried on the sensitive emulsion support such as the backing layer or supercoat.
- the sensitive layer may be bathed in a solution of the agent before or after exposure.
- the substance is added to the emulsion layer in amounts corresponding to 0.1 to 6.0 g., but preferably about 0.5 to 1.5 g./litre of finished emulsion, or to a developer or fixing bath at the rate of 0.2 to 4.0 g. per litre, preferably about 1 g. per litre.
- the layer is simply bathed in a solution of the. compound this may contain up to 5% of the compound in Water.
- the compounds are very effective as antipluinming agents when used in any of the Ways previously described or by bathing the image in the solution of the compound after fixation.
- the agent is preferably added to the developing solutions (when not already present in the photographic material) it may be added in the fixing bath or at any stage prior to Washing since sufficient of the compound will be adsorbed to the silver grains to give the desired anti-plumming effect during hot-glazing of the print.
- Example 4 S-amidoethylthiuronium chloride Finely powdered thiourea (15.2 g.), chloracet amide- (18.7 g.) and ethyl alcohol (190 0.0.) were refluxed for 2 hours. The salt which separated during. this time-was-collected hot, washed with alcohol and ether and dried. From water it formed colourless needles, M.P. 222 C. (decomp).
- Example 5 S-2-thiazylamidomethylthiuronium chloride Z-chloracetamidothiazole was obtained by chloracetylating 2-aminothiazole in pyridine, and precipitating the amide with acetic acid. This product (2.3g),powderedthiourea (1.3 g.) and ethyl alcohol (40 0.0.) were refluxed for 2 hours. Crystallization commenced after 5 mins. It was collected, washed with alcohol and recrystallized from. a little water forming fawn needles, M.P. 231 C. (decomp.).
- Example 6.-S'-2-pyridylamidomethylthiuroniam chloride NHzCl 2-chloracetamidopyridine was obtained by treating 2-aminopyridine with chloracetyl chloride in pyridine and precipitating with dilute acetic acid. This product (2.3 g.), thiourea (1.1 g.) and ethyl alcohol cc.) were refluxed for 2 hours. The crystals which had separated were collected, washed with alcohol, and. recrystallized from a little water. forming fawn. needles, M.P. 225 C. (decomp).
- Example A 1 g. of S-ethylthiuronium bromide added to 1 litre of a silver chloride emulsion (containing approx. 20 g. AgCl per litre) gave an image of slightly bluer tone when the emulsion was coated on paper, exposed, and developed in a normal metol-hydroquinone developer. The maximum density obtainable was slightly increased, and did not decrease on hot glazing, unlike that of the untreated emulsion.
- Example B The 1 g. of S-ethylthiuronium bromide used in Example A above was replaced by 1 g. of each of the compounds described in Examples 2, 3 or 4 and similar. results obtained.
- Example C Replacement of S-ethylthiuronium bromide in Example A by the compound described in Example 5 or 6 gave a still bluer image and higher maximum density, with no loss on hot glazing.
- Example D 1 g. of the compound described in Example 6 added to 1 litre of a silver chlorobromide emulsion changed the normal warm brown tone of the blacks to neutral, On development in a normal metol-hydroquinone developer. There was also a large increase in maximum density, and no plumming on glazing, although this emulsion lost density badly on glazing when untreated. Addition of as little as 0.2 g./litre of the compound of Example 6 was appropriate to stop this plumming.
- Example E (a) A silver ohloro-bromide emulsion coated on paper was exposed to a step wedge, developed and fixed.
- a gelatino-silver halide emulsion contain ng as an anti-plumming agent a compound represented by the formula:
- R represents an alkyl group and X rep-- resents a halogen atom.
- R represents. an, amido-substituted'. alkyl group and)! represents. a halogenatom.
- YNH-O o-c m-s-O NH wherein Y represents a nitrogen-containing heterocyclic residue and X represents a halogen atom.
- R represents an alkyl group and X represents a halogen atom.
- R represents an amido-substituted alkyl group and X represents a halogen atom.
- Y represents a member selcted from the group consisting of a pyridyl group, a quinolyl group, a thiazyl group, a benzthiazyl group and a pyrimidyl group and X represents a halogen atom.
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)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB18566/46A GB613400A (en) | 1946-06-20 | 1946-06-20 | Improvements in and relating to photographic materials |
Publications (1)
Publication Number | Publication Date |
---|---|
US2461987A true US2461987A (en) | 1949-02-15 |
Family
ID=10114651
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US755718A Expired - Lifetime US2461987A (en) | 1946-06-20 | 1947-06-19 | Antiplumming agents for photographic emulsions |
Country Status (4)
Country | Link |
---|---|
US (1) | US2461987A (en(2012)) |
BE (1) | BE476658A (en(2012)) |
FR (1) | FR953604A (en(2012)) |
GB (1) | GB613400A (en(2012)) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3220839A (en) * | 1961-08-25 | 1965-11-30 | Eastman Kodak Co | Photographic emulsions containing isothiourea derivatives |
US5380626A (en) * | 1992-04-06 | 1995-01-10 | Fuji Photo Film Co., Ltd. | Method for processing a silver halide photographic material using a processing solution having a bleaching ability containing one of an amidine or a bisguanidine compound |
US20110034521A1 (en) * | 2007-09-28 | 2011-02-10 | Alan Jacobson | Compounds and methods for treating zinc matrix metalloprotease dependent diseases |
US20110190285A1 (en) * | 2008-09-19 | 2011-08-04 | Absolute Science, Inc. | Methods of treating a botulinum toxin related condition in a subject |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2124159A (en) * | 1933-05-24 | 1938-07-19 | Agfa Ansco Corp | Method of increasing the brilliancy of photographic pictures, and composition therefor |
US2255731A (en) * | 1940-03-15 | 1941-09-09 | American Cyanamid Co | Photographic developer |
-
0
- BE BE476658D patent/BE476658A/xx unknown
-
1946
- 1946-06-20 GB GB18566/46A patent/GB613400A/en not_active Expired
-
1947
- 1947-06-19 US US755718A patent/US2461987A/en not_active Expired - Lifetime
- 1947-09-29 FR FR953604D patent/FR953604A/fr not_active Expired
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2124159A (en) * | 1933-05-24 | 1938-07-19 | Agfa Ansco Corp | Method of increasing the brilliancy of photographic pictures, and composition therefor |
US2255731A (en) * | 1940-03-15 | 1941-09-09 | American Cyanamid Co | Photographic developer |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3220839A (en) * | 1961-08-25 | 1965-11-30 | Eastman Kodak Co | Photographic emulsions containing isothiourea derivatives |
US5380626A (en) * | 1992-04-06 | 1995-01-10 | Fuji Photo Film Co., Ltd. | Method for processing a silver halide photographic material using a processing solution having a bleaching ability containing one of an amidine or a bisguanidine compound |
US20110034521A1 (en) * | 2007-09-28 | 2011-02-10 | Alan Jacobson | Compounds and methods for treating zinc matrix metalloprotease dependent diseases |
EP2190293A4 (en) * | 2007-09-28 | 2011-11-09 | Absolute Science Inc | COMPOUNDS AND METHOD FOR THE TREATMENT OF DISEASES MEDIATED BY ZINC MATRIX METALLOPROTEASE |
US20110190285A1 (en) * | 2008-09-19 | 2011-08-04 | Absolute Science, Inc. | Methods of treating a botulinum toxin related condition in a subject |
Also Published As
Publication number | Publication date |
---|---|
BE476658A (en(2012)) | |
FR953604A (fr) | 1949-12-09 |
GB613400A (en) | 1948-11-25 |
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