US2590775A - Silver halide emulsion containing a thio-imino-urazole as a stabilizer - Google Patents
Silver halide emulsion containing a thio-imino-urazole as a stabilizer Download PDFInfo
- Publication number
- US2590775A US2590775A US155356A US15535650A US2590775A US 2590775 A US2590775 A US 2590775A US 155356 A US155356 A US 155356A US 15535650 A US15535650 A US 15535650A US 2590775 A US2590775 A US 2590775A
- Authority
- US
- United States
- Prior art keywords
- silver halide
- thio
- photographic
- emulsions
- urazole
- 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 claims description 35
- 229910052709 silver Inorganic materials 0.000 title claims description 21
- 239000004332 silver Substances 0.000 title claims description 21
- -1 Silver halide Chemical class 0.000 title claims description 19
- 239000003381 stabilizer Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims description 11
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 description 17
- 238000012545 processing Methods 0.000 description 9
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229910021607 Silver chloride Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GPUADMRJQVPIAS-QCVDVZFFSA-M cerivastatin sodium Chemical compound [Na+].COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 GPUADMRJQVPIAS-QCVDVZFFSA-M 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002699 waste material 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
- G03C1/346—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 compounds hi when ncl ded a photogra hi sil er hal de emulsion la or in a or l er p e en in a Photographic mate a includin such e niilo e r o he develo erl f or o other processing bath applie t the. photo ra ic m terial, improve the.
- R is a hydrogen atom or a hydrocarbon group.
- the said compounds may be defined as 3-thio- 5-iminourazoles and may be prepared by well k w methodso examp the compound in which R is a hydrogen atom may be prepared by the method described in Liebigs Annalen der Chemie, volume 426, at page 313, and the compound where R is a phenyl group may be prepared by the method described in Berichte der Deutschen Chemischen Deutschentechnik, volume 55, at page 12. These two compounds are the preferred compounds for use in the present invention, but the invention also includes the use of compounds where R represents other hydrocarbon groups, e. g. alkyl. such as methyl, ethyl and higher alkyl, aralkyl, such as benzyl, and other aryl groups. such as naphthyl.
- R represents other hydrocarbon groups, e. g. alkyl. such as methyl, ethyl and higher alkyl, aralkyl, such as benzyl, and other aryl groups. such as naphthyl.
- the compounds may be used as free bases or as ammonium or alkali metal salts. They may also be used in the form of their substantially water-insoluble colourless metal derivatives, said metal derivatives being soluble or decomposible during treatment of the photographic element with processing baths subsequent to the development of the element.
- metal salts may be silver or nickel or other metal mentioned in British Specification No. 573,745 to which reiere once is made for details of this aspect of the invention.
- these compounds may be included in the silver halide photographic emulsion or in another layer of the photographic element, preferably coated adjacent to such emulsion layer, for example in a sub-coat layer or in
- the optimum quantity of compound to be employed will always be small, but will depend on the particular substance selected. In general it is found that for incorporation in an emulsion, sub-coat or super-coat, a proportion of 1 part of the compound in 1000. to 900 o t e emu s u e t or S bsolution is generally suitable, While for incorporas tion in a developer, fixer or other treatment bath, e.
- the optimum quantity may be, ior'example, between 1 part in 300.0 to 1 part in 300,000 parts of the processing so1ution. Frequently even lower concentrations than those given above have some effect and, though it may be uneconomic in being a waste of material, even higher concentrations may be employed.
- More than one compound of the type defined may be used if desired, and the compound or compounds may be used in more than one way, e, g. in super-coat and developing solution, or in both developing and fixing solutions.
- the compounds will be applied to the photographic emulsion before reaching the final stage of drying the developed image, but they may be applied with advantage to already dri d pr nt w r it is e red o sub c e latter to hot-glazing.
- Example 1 To a gelatin super-coat solution was added a solution of 3-thio-5 -iminourazole in the proportion of 1 part of the compound per 5000 parts of the gelatin solution by weight. This supercoat was applied over- (A) A silver chloride photographic emulsion of the type known as vigorous gaslight.
- Example 2 A silver chloride photographic printing paper of the type known as vigorous gaslight was exposed and developed in a standard metolhydroquinone developer, fixed, washed and hotglazed. Small quantities of 3-thio-5-phenyliminourazole were added to the developing bath and, in a second test, to the acid fixing bath, and the following results were obtained.
- a method of improving photographic silver halide emulsions in regard to the quality of the. images developed therein which comprises developing such emulsions in a developing bath which contains a small quantity of 3-thio-5- phenyliminourazole.
- a method of improving photographic silver halide emulsions in regard to the quality of the images developed therein which comprises developing such emulsions in a developing bath which contains a small quantity of 3-thio-5- iminourazole.
- a method of improving photographic silver halide emulsions in regard to the quality of the images developed therein which comprises developing such emulsions and thereafter fixin the emulsions in a fixing bath containing a small quantity of 3-thio-5-phenyliminourazole.
- a method of improving photographic silver halide emulsions in regard to the quality of the images developed therein which comprises developing such emulsions and thereafter fixin the emulsions in a fixing bath containing a small quantity of 3-thio-5-iminourazole.
- a photographic element which includes a silver halide photographic emulsion layer and in contact therewith uniformly throughout, a small quantity of a heterocyclic compound of the general formula:
- R is selected from the class consisting of the hydrogen atom and hydrocarbon groups.
- a photographic element which includes a silver halide photographic emulsion layer and in contact therewith uniformly throughout, a small quantity of 3-thio-5-phenyliminourazole.
- a photographic element which includes a silver halide photographic emulsion layer and in contact therewith uniformly throughout, a small quantity of 3-thio-5-iminourazole.
- a photographic element which comprises a silver halide photographic emulsion layer and coated adjacent thereto a water-permeable colloid layer which contains a small proportion of 3-thio-5-phenyliminourazole.
- a photographic element which comprises a silver halide photographic emulsion layer and coated adjacent thereto a water-permeable colloid layer which contains a small proportion of 3-thio-5-iminourazole.
- a method of improving photographic silver halide emulsions in regard to the quality of the images developed therein which comprises treating such emulsions with photographic processing baths in the presence, at least at one stage in the processing, of a heterocyclic compound of the general formula:
- R is selected from the class consisting of the hydrogen atom and hydrocarbon groups.
- a method of improving photographic silver halide emulsions in regard to the quality of the images developed therein which comprises treating such emulsions with photographic processing baths in the presence, at least at one stage in the processing, of a small quantity of 3-thio-5- phenyliminourazole.
- a method of improving photographic silver halide emulsions in regard to the quality of the images developed therein which comprises treating such emulsions with photographic processing baths in the presence, at least at one stage in the processing, of a small quantity of 3-thio5- iminourazole.
Description
atented Mar. 25 1952 SILVER HALIDE EMULSIQN CONTAINING A THIO-I-MINO-URAZOLE AS A STABILIZEB John David Kendall and Douglas James Fry, more. England, assignors to Ilford Limited, Il or Eng and, a. British com ny No Drawing. Application April 11, 1950, Serial No. 155,356. In Great Britain April 11, 1949 12 Claims. (01. 95-4) This invention relates to compounds hi when ncl ded a photogra hi sil er hal de emulsion la or in a or l er p e en in a Photographic mate a includin such e niilo e r o he develo erl f or o other processing bath applie t the. photo ra ic m terial, improve the. qual ty of the de elop d hotographic ima es ob a n d- In the production of photo aph c ima n silver halide emulsions, and particularly in the case of emuls ns n when the sil er ha i e is predominantl silver chi id the maximum mage density obt inable is not always so re t as m y be desire Moreover, the com on p actice of hot-glazin photo raphic p ints. tends to affect adversely the image olour ivin a p o qua ty ack hav ng a bronzed appearance, and also reduces the eiiective maximum density obtainable in the image.
It has now been discovered that this bronzing efiect may be reduced or eliminated and the maximum d ty obt ina le may be nc e ed b bringing into contact with the photographic emuls o a m mber or a certa n c as o het r cyc nitrogen compounds, and according to this invention, therefore a method of improving photoh c silver h e e lsions n r ga d to the quality of the images developed therein comprises applying to such emulsions, e. g. by including in the emulsion, or in another layer of the photo.- graphic element containing such emulsion, or in a developing, fixing or othe ocessing bath with wh h the photographic elem nt s t ea e a heterocyclic compound of the general rormula:
where R is a hydrogen atom or a hydrocarbon group.
The said compounds may be defined as 3-thio- 5-iminourazoles and may be prepared by well k w methodso examp the compound in which R is a hydrogen atom may be prepared by the method described in Liebigs Annalen der Chemie, volume 426, at page 313, and the compound where R is a phenyl group may be prepared by the method described in Berichte der Deutschen Chemischen Gesellschaft, volume 55, at page 12. These two compounds are the preferred compounds for use in the present invention, but the invention also includes the use of compounds where R represents other hydrocarbon groups, e. g. alkyl. such as methyl, ethyl and higher alkyl, aralkyl, such as benzyl, and other aryl groups. such as naphthyl.
a superecoat layer.
The compounds may be used as free bases or as ammonium or alkali metal salts. They may also be used in the form of their substantially water-insoluble colourless metal derivatives, said metal derivatives being soluble or decomposible during treatment of the photographic element with processing baths subsequent to the development of the element. Such metal salts may be silver or nickel or other metal mentioned in British Specification No. 573,745 to which reiere once is made for details of this aspect of the invention. V
As already indicated these compounds may be included in the silver halide photographic emulsion or in another layer of the photographic element, preferably coated adjacent to such emulsion layer, for example in a sub-coat layer or in The optimum quantity of compound to be employed will always be small, but will depend on the particular substance selected. In general it is found that for incorporation in an emulsion, sub-coat or super-coat, a proportion of 1 part of the compound in 1000. to 900 o t e emu s u e t or S bsolution is generally suitable, While for incorporas tion in a developer, fixer or other treatment bath, e. g, a glazing solution, the optimum quantity may be, ior'example, between 1 part in 300.0 to 1 part in 300,000 parts of the processing so1ution. Frequently even lower concentrations than those given above have some effect and, though it may be uneconomic in being a waste of material, even higher concentrations may be employed.
More than one compound of the type defined may be used if desired, and the compound or compounds may be used in more than one way, e, g. in super-coat and developing solution, or in both developing and fixing solutions.
Mixtures of the compounds with any of those specified for similar use in British Specifications Nos. 573,745 and 583,648 may also be employed.
In general the compounds will be applied to the photographic emulsion before reaching the final stage of drying the developed image, but they may be applied with advantage to already dri d pr nt w r it is e red o sub c e latter to hot-glazing. V a
The following examples illustrate the invention:
Example 1 To a gelatin super-coat solution was added a solution of 3-thio-5 -iminourazole in the proportion of 1 part of the compound per 5000 parts of the gelatin solution by weight. This supercoat was applied over- (A) A silver chloride photographic emulsion of the type known as vigorous gaslight.
lglaxiltnunli lvflaximtum ensl y ms y Emulswn (A 15) cold-dried after hot coatings glazing Control A 1.84 1.50 Test A 1.87 1.95 Control B.-. 1.90 l. 65 Test B 1. 94 2.01
Example 2 A silver chloride photographic printing paper of the type known as vigorous gaslight was exposed and developed in a standard metolhydroquinone developer, fixed, washed and hotglazed. Small quantities of 3-thio-5-phenyliminourazole were added to the developing bath and, in a second test, to the acid fixing bath, and the following results were obtained.
- Maximum Test gy elq 8335 A i a non a at o addition glazing Control None None 1.41 A lpart per do 2.02
1,000. B None One part 1.76
per 10,- 000.
What we claim is:
1. A method of improving photographic silver halide emulsions in regard to the quality of the. images developed therein which comprises developing such emulsions in a developing bath which contains a small quantity of 3-thio-5- phenyliminourazole.
2. A method of improving photographic silver halide emulsions in regard to the quality of the images developed therein which comprises developing such emulsions in a developing bath which contains a small quantity of 3-thio-5- iminourazole.
3. A method of improving photographic silver halide emulsions in regard to the quality of the images developed therein which comprises developing such emulsions and thereafter fixin the emulsions in a fixing bath containing a small quantity of 3-thio-5-phenyliminourazole.
4. A method of improving photographic silver halide emulsions in regard to the quality of the images developed therein which comprises developing such emulsions and thereafter fixin the emulsions in a fixing bath containing a small quantity of 3-thio-5-iminourazole.
5. A photographic element which includes a silver halide photographic emulsion layer and in contact therewith uniformly throughout, a small quantity of a heterocyclic compound of the general formula:
.where R is selected from the class consisting of the hydrogen atom and hydrocarbon groups.
6. A photographic element which includes a silver halide photographic emulsion layer and in contact therewith uniformly throughout, a small quantity of 3-thio-5-phenyliminourazole.
7. A photographic element which includes a silver halide photographic emulsion layer and in contact therewith uniformly throughout, a small quantity of 3-thio-5-iminourazole.
8. A photographic element which comprises a silver halide photographic emulsion layer and coated adjacent thereto a water-permeable colloid layer which contains a small proportion of 3-thio-5-phenyliminourazole.
9. A photographic element which comprises a silver halide photographic emulsion layer and coated adjacent thereto a water-permeable colloid layer which contains a small proportion of 3-thio-5-iminourazole.
10. A method of improving photographic silver halide emulsions in regard to the quality of the images developed therein which comprises treating such emulsions with photographic processing baths in the presence, at least at one stage in the processing, of a heterocyclic compound of the general formula:
where R is selected from the class consisting of the hydrogen atom and hydrocarbon groups.
11. A method of improving photographic silver halide emulsions in regard to the quality of the images developed therein which comprises treating such emulsions with photographic processing baths in the presence, at least at one stage in the processing, of a small quantity of 3-thio-5- phenyliminourazole.
12. A method of improving photographic silver halide emulsions in regard to the quality of the images developed therein which comprises treating such emulsions with photographic processing baths in the presence, at least at one stage in the processing, of a small quantity of 3-thio5- iminourazole.
JOHN DAVID KENDALL. DOUGLAS JAMES FRY.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date I 1,560,240 Jelley Nov. 3, 1925 2,298,093 Dersch Oct. 6, 1942 2,363,493 Baldsiefen Nov. 28, 1944
Claims (2)
- 2. A METHOD OF IMPROVING PHOTOGRAPHIC SILVER HALIDE EMULSIONS IN REGARD TO THE QUALITY OF THE IMAGES DEVELOPED THEREIN WHICH COMPRISES DEVELOPING SUCH EMULSIONS IN A DEVELOPING BATH WHICH CONTAINS A SMALL QUANTITY OF 3-THIO-5IMINOURAZOLE.
- 5. A PHOTOGRAPHIC ELEMENT WHICH INCLUDES A SILVER HALIDE PHOTOGRAPHIC EMULSION LAYER AND IN CONTACT THEREWITH UNIFORMLY THROUGHOUT, A SMALL QUANTITY OF A HETEROCYCLIC COMPOUND OF THE GENERAL FORMULA:
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9811/49A GB660856A (en) | 1949-04-11 | 1949-04-11 | Improvements in or relating to photographic materials |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2590775A true US2590775A (en) | 1952-03-25 |
Family
ID=9879237
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US155356A Expired - Lifetime US2590775A (en) | 1949-04-11 | 1950-04-11 | Silver halide emulsion containing a thio-imino-urazole as a stabilizer |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2590775A (en) |
| GB (1) | GB660856A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2857276A (en) * | 1954-11-23 | 1958-10-21 | Polaroid Corp | Photographic processes and compositions useful therein |
| US2857274A (en) * | 1953-09-04 | 1958-10-21 | Polaroid Corp | Photographic compositions and processes |
| US2857275A (en) * | 1954-11-08 | 1958-10-21 | Polaroid Corp | Photographic compositions and processes |
| US3438777A (en) * | 1966-02-14 | 1969-04-15 | Agfa Gevaert Nv | Photographic material |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1560240A (en) * | 1924-08-11 | 1925-11-03 | Jelley Edwin Ernest | Photographic sensitizer |
| US2298093A (en) * | 1940-10-15 | 1942-10-06 | Gen Aniline & Film Corp | Production of photographs in blueblack tones |
| US2363493A (en) * | 1941-06-13 | 1944-11-28 | Du Pont | Photographic processes and compositions |
-
1949
- 1949-04-11 GB GB9811/49A patent/GB660856A/en not_active Expired
-
1950
- 1950-04-11 US US155356A patent/US2590775A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1560240A (en) * | 1924-08-11 | 1925-11-03 | Jelley Edwin Ernest | Photographic sensitizer |
| US2298093A (en) * | 1940-10-15 | 1942-10-06 | Gen Aniline & Film Corp | Production of photographs in blueblack tones |
| US2363493A (en) * | 1941-06-13 | 1944-11-28 | Du Pont | Photographic processes and compositions |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2857274A (en) * | 1953-09-04 | 1958-10-21 | Polaroid Corp | Photographic compositions and processes |
| US2857275A (en) * | 1954-11-08 | 1958-10-21 | Polaroid Corp | Photographic compositions and processes |
| US2857276A (en) * | 1954-11-23 | 1958-10-21 | Polaroid Corp | Photographic processes and compositions useful therein |
| US3438777A (en) * | 1966-02-14 | 1969-04-15 | Agfa Gevaert Nv | Photographic material |
Also Published As
| Publication number | Publication date |
|---|---|
| GB660856A (en) | 1951-11-14 |
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