US2578655A - Photographic silver halide emulsions containing 4-hydroxy quinolines - Google Patents
Photographic silver halide emulsions containing 4-hydroxy quinolines Download PDFInfo
- Publication number
- US2578655A US2578655A US91639A US9163949A US2578655A US 2578655 A US2578655 A US 2578655A US 91639 A US91639 A US 91639A US 9163949 A US9163949 A US 9163949A US 2578655 A US2578655 A US 2578655A
- Authority
- US
- United States
- Prior art keywords
- emulsion
- compound
- hydroxy
- photographic
- quinoline
- 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 38
- 150000004331 4-hydroxyquinolines Chemical class 0.000 title claims description 8
- -1 silver halide Chemical class 0.000 title description 4
- 229910052709 silver Inorganic materials 0.000 title description 3
- 239000004332 silver Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 37
- SJOOOZPMQAWAOP-UHFFFAOYSA-N [Ag].BrCl Chemical compound [Ag].BrCl SJOOOZPMQAWAOP-UHFFFAOYSA-N 0.000 claims description 12
- PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical compound C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 claims description 6
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical class O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 5
- NWINIEGDLHHNLH-UHFFFAOYSA-N 2-methyl-1h-quinolin-4-one Chemical compound C1=CC=CC2=NC(C)=CC(O)=C21 NWINIEGDLHHNLH-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910021607 Silver chloride Inorganic materials 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical group [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- NZXUIQMHGFPOHI-UHFFFAOYSA-N 3-acetyl-1h-quinolin-4-one Chemical compound C1=CC=C2C(=O)C(C(=O)C)=CNC2=C1 NZXUIQMHGFPOHI-UHFFFAOYSA-N 0.000 description 1
- ILNJBIQQAIIMEY-UHFFFAOYSA-N 4-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CN=C21 ILNJBIQQAIIMEY-UHFFFAOYSA-N 0.000 description 1
- PJEUKNUOCWNERE-UHFFFAOYSA-N 6-methyl-1h-quinolin-4-one Chemical compound N1=CC=C(O)C2=CC(C)=CC=C21 PJEUKNUOCWNERE-UHFFFAOYSA-N 0.000 description 1
- HTISUYZVEWQIMP-UHFFFAOYSA-N 8-methyl-1h-quinolin-4-one Chemical compound C1=CN=C2C(C)=CC=CC2=C1O HTISUYZVEWQIMP-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002723 alicyclic group Chemical class 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
-
- 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
- Y10S430/166—Toner containing
Definitions
- R1 is an unsubstituted alkyl or aralkyl group
- R2 is a hydrogen atom or an alkyl or aralkyl group (or R1 and R2 together constitute the residue of an alicyclic nucleus)
- R3 is a hydrogen atom or a lower alkyl group.
- substituents other than amino or substituted amino
- the developed images obtained from the silver chloride emulsions have a. bluish tone.
- the tone of the developed image may be made warmer, i. e. inclining to a brownish-black, by including in such emulsions one or more of a narrow class of quinoline compounds, and according to the present invention silver chlorobromide emulsions which yield images of brown-black colour on development are obtained by including in the emulsion, during its manufacture, 4-hydroxy quinoline or a 4-hydroxy quinoline containing one or more nuclear substituents selected from alkyl, e. g. methyl, ethyl, propyl and butyl, acyl, e. g.
- acetyl, propionyl and butyryl carboxy and carbalkoxy, e. g. carbethoxy groups.
- carboxy groups e. g. carbethoxy groups.
- salts of such compounds e. g. the sodium salts, may be employed.
- R1 to Rs are hydrogen atoms and the remaining R groups are alkyl, acyl, carboxy or carbalkoxy, for example any of those listed above, but not more than one of the R groups is acyl, carboxy or carbalkoxy.
- the proportion of the compound added to the emulsion will depend on the particular compound used. In general satisfactory brown-black tones are obtained using proportions of the order of 0.2 to 25 cc. of a 1% solution of the compound per pound of emulsion.
- the emulsion may be washed or unwashed.
- gelatino silver chlorobromide emulsion was: prepared and to portions of it were added pro-- portions of compounds according to this inven tion. Each compound was added at the rate of.”
- a photographic silver chlorobromide emulsion which yields images of brown-black tone on normal photographic development which emulsion includes 4-hydr0Xy-6-methyl quinolinethe proportion of the said compound being equivalent to 0.2 to 25 cubic centimeters of a 1% solution of the compound per pound ofemulsion.
- a photographic silver chlorobromide emulsion which yields images of brown-black tone on normal photographic development which includes 3-acetyl-4-hydroxy quinoline the proportion of the said compound being equivalent to 0.2 to 25 cubic centimeters of a 1% solution ofthe compound per pound of emulsion.
- a photographic silver chlorobromide emulsion which yields images of brown-black tone on normal photographic development which includes a compound selected from the class consisting of 4-hydroxy quinoline, 4-hydroxy quinolines containing a single nuclear alkyl substituent and 4-hydroxy quinolines containing in the 3- position acyl, carboxy and carbalkoxy groups, the proportion of the said compound being equivalent to 0.2 to 25 cc: of a 1% solution of the compound perpound of'emulsion.
- a photographic element consisting of a paper support carrying a photographic silver chlorobromide' emulsion which yields images of brown-black tone on normal photographic development which includes a compound selected from the class consisting of 4-hydroxy quinoline, 4-hydroxy quinolines'containing a single nuclear alkyl'substitutent and 4-hydroxyquinolines containing in the 3-position acyl, carboxyl and carbalkoxy groups, the proportion of the said compound being equivalent to 0.2 to 25 cc. of a 1% solution of the compound per pound of emulsion.
- a photographic silvenchlorobromide emulsion which yields images of brown-black tone on normal photographic development which emulsion includes 2-methyl-4-hydroxy quinoline, the proportion. of. the said compound being equivalent to 0.2 to 25 cc. of a 1% solution of the compoundzperi pound of emulsion.
- a photographic silver chlorobromide emulsion which yieldsimages of brown-black tone on. normal photographic development which emulsion includes 8'-methyl-4-hydroxy quinoline, the proportion of the said compound being equivalent to 0.2 to 25 cc. of a 1% solution of the compound per pound of emulsion.
- a photographic silver chlorobromide emulsion which yields images of brown-black, tone on normal.
- photographic development which emulsion includes. 4-hydroxy quinoline 3-carboxylic acid, the proportion of said compound being equivalent to 0.2 to 25 cc. of a 1% solution of the compound'per pound of emulsion.
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- 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)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Patented Dec. 18, i951 PHOTOGRAPH-IO SILVER HALIDE EMUL- SIONS CONTAINING 4-HYDROXY QUIN- OLINES John David Kendall and Douglas James Fry, Ilford, England, assignors to Ilford Limited, Ilford, England, a British company No Drawing. Application May 5, 1949, Serial No. 91,639. In Great Britain May 8, 1948 This invention relates to photographic materials and particularly to photographic materials in which the light-sensitive layer consists of a silver chlorobromide emulsion.
It iswell known that the addition of various compounds to photographic silver halide emulsions has an effect on the colour of the developed image. Thus United States Patent No. 2,397,015 corresponding to British Patent No. 563,498 describes the production of photographic light-sensitive elements in which the light-sensitive layer is a silver chloride emulsion containing a quinoline compound of the formula:
\N Ra where R1 is an unsubstituted alkyl or aralkyl group, R2 is a hydrogen atom or an alkyl or aralkyl group (or R1 and R2 together constitute the residue of an alicyclic nucleus) and R3 is a hydrogen atom or a lower alkyl group. Derivatives of these compounds containing substituents (other than amino or substituted amino) in the carbocyclic ring and mineral acid salts of any of such compounds may alternatively be employed. By reason of the presence of these quinoline compounds the developed images obtained from the silver chloride emulsions have a. bluish tone.
The action of such compounds in modifying the tone of the developed image is highly specific and it is to be noted that United States Patent No. 2,397,015 corresponding to British Patent No. 563,498 claims the use of this narrow class of compounds for use with a certain specific type of emulsion.
It has now been found that in silver chlorobromide emulsions the tone of the developed image may be made warmer, i. e. inclining to a brownish-black, by including in such emulsions one or more of a narrow class of quinoline compounds, and according to the present invention silver chlorobromide emulsions which yield images of brown-black colour on development are obtained by including in the emulsion, during its manufacture, 4-hydroxy quinoline or a 4-hydroxy quinoline containing one or more nuclear substituents selected from alkyl, e. g. methyl, ethyl, propyl and butyl, acyl, e. g. acetyl, propionyl and butyryl, carboxy and carbalkoxy, e. g. carbethoxy groups. In the case of compounds containing carboxy groups the salts of such compounds, e. g. the sodium salts, may be employed.
7 Claims. (01. 957) Preferably, according to the invention, there is included in a gelatino silver chlorobromide emulsion, during the manufacture of the emulsion, a compound of the general formula:
R, on
wherein at least three of the groups R1 to Rs are hydrogen atoms and the remaining R groups are alkyl, acyl, carboxy or carbalkoxy, for example any of those listed above, but not more than one of the R groups is acyl, carboxy or carbalkoxy.
The proportion of the compound added to the emulsion will depend on the particular compound used. In general satisfactory brown-black tones are obtained using proportions of the order of 0.2 to 25 cc. of a 1% solution of the compound per pound of emulsion. The emulsion may be washed or unwashed.
It is an important advantage of the compounds of this invention and distinguishes them from other compounds which have some browning effect on the image colour, that the compounds are without any appreciable deleterious effect on the speed and contrast of the emulsion, and do not cause fogging of the emulsion.
tion
Examples A gelatino silver chlorobromide emulsion was: prepared and to portions of it were added pro-- portions of compounds according to this inven tion. Each compound was added at the rate of."
ggp Compound Image Colour 1 4-hydroxy quinoline Warmer than control.
4-hydroxy-8-methyl-quinoline Do. 4-hydroxy-6-methyl-quinoline Mucht ilvarmer than con r0 3-acetyl-4-hyclroxy-quinoline Do. 4-hdroxkyi-quino1ine-3-carbox- Warmer than control.
y lo ac 6 2-methyl-4hydroxy-quinoline. Do.
The following examples illustrate the inven--- The compound of Example was tested as the sodium salt.
Other compounds in the series gave very similar results.
What we claim is:
1. A photographic silver chlorobromide emulsion which yields images of brown-black tone on normal photographic development which emulsion includes 4-hydr0Xy-6-methyl quinolinethe proportion of the said compound being equivalent to 0.2 to 25 cubic centimeters of a 1% solution of the compound per pound ofemulsion.
2. A photographic silver chlorobromide emulsion which yields images of brown-black tone on normal photographic development which includes 3-acetyl-4-hydroxy quinoline the proportion of the said compound being equivalent to 0.2 to 25 cubic centimeters of a 1% solution ofthe compound per pound of emulsion.
3. A photographic silver chlorobromide emulsion which yields images of brown-black tone on normal photographic development which includes a compound selected from the class consisting of 4-hydroxy quinoline, 4-hydroxy quinolines containing a single nuclear alkyl substituent and 4-hydroxy quinolines containing in the 3- position acyl, carboxy and carbalkoxy groups, the proportion of the said compound being equivalent to 0.2 to 25 cc: of a 1% solution of the compound perpound of'emulsion.
4. A photographic element consisting of a paper support carrying a photographic silver chlorobromide' emulsion which yields images of brown-black tone on normal photographic development which includes a compound selected from the class consisting of 4-hydroxy quinoline, 4-hydroxy quinolines'containing a single nuclear alkyl'substitutent and 4-hydroxyquinolines containing in the 3-position acyl, carboxyl and carbalkoxy groups, the proportion of the said compound being equivalent to 0.2 to 25 cc. of a 1% solution of the compound per pound of emulsion.
. 5. A photographic silvenchlorobromide emulsion which yields images of brown-black tone on normal photographic development which emulsion includes 2-methyl-4-hydroxy quinoline, the proportion. of. the said compound being equivalent to 0.2 to 25 cc. of a 1% solution of the compoundzperi pound of emulsion.
6. A photographic silver chlorobromide emulsion: which yieldsimages of brown-black tone on. normal photographic development which emulsion includes 8'-methyl-4-hydroxy quinoline, the proportion of the said compound being equivalent to 0.2 to 25 cc. of a 1% solution of the compound per pound of emulsion.
7'. A photographic silver chlorobromide emulsion which yields images of brown-black, tone on normal. photographic development which emulsion includes. 4-hydroxy quinoline 3-carboxylic acid, the proportion of said compound being equivalent to 0.2 to 25 cc. of a 1% solution of the compound'per pound of emulsion.
JOHN DAVID KENDALL. DOUGLAS. JAMES FRY.
REFERENCES CITED The following referencesare of record in the file of'this patent:
UNITED STATES PATENTS Number Name Date 2,395,846 Carroll et al Mar. 5, 1946 2,397,015 Kendall et al Mar. 19, 1946 FOREIGN PATENTS Number Country Date.
No. 371 Great Britain 1896 596,105 Germany Apr. 26,1934 768,519 France Aug. 7, 1934
Claims (1)
- 3. A PHOTOGRAPHIC SILVER CHLOROBROMIDE EMULSION WHICH YIELDS IMAGES OF BROWN-BLACK TONE ON NORMAL PHOTOGRAPHIC DEVELOPMENT WHICH INCLUDES A COMPOUND SELECTED FROM THE CLASS CONSISTING OF 4-HYDROXY QUINOLINE, 4-HYDROXY QUINOLINES CONTAINING A SINGLE NUCLEAR ALKYL SUBSTITUENT AND 4-HYDROXY QUINOLINES CONTAINING IN THE 3POSITION ACYL, CARBOXY AND CARBALKOXY GROUPS, THE PROPORTION OF THE SAID COMPOUND BEING EQUIVALENT TO 0.2 TO 25 CC. OF A 1% SOLUTION OF THE COMPOUND PER POUND OF EMULSION.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB12697/48A GB637847A (en) | 1948-05-08 | 1948-05-08 | Improvements in or relating to photographic materials |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2578655A true US2578655A (en) | 1951-12-18 |
Family
ID=10009442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US91639A Expired - Lifetime US2578655A (en) | 1948-05-08 | 1949-05-05 | Photographic silver halide emulsions containing 4-hydroxy quinolines |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2578655A (en) |
| GB (1) | GB637847A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3446618A (en) * | 1965-11-08 | 1969-05-27 | Gaf Corp | Photographic silver halide emulsions containing trifluoromethyl - 4 - hydroxy quinoline carboxy acid salt as a stabilizer |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB189600371A (en) * | 1896-01-06 | 1896-11-14 | Lembach & Schleicher | Improvements in Photographic Developers. |
| DE596105C (en) * | 1932-09-28 | 1934-04-26 | Heinz Gossler Dr | Process for adding quinine salts and other blue-black developing compounds which tend to form precipitates in the developer |
| FR768519A (en) * | 1934-02-14 | 1934-08-07 | Ig Farbenindustrie Ag | Method for determining shades of photographic developing images |
| US2395846A (en) * | 1944-06-13 | 1946-03-05 | Eastman Kodak Co | Sensitized photographic emulsion |
| US2397015A (en) * | 1943-02-12 | 1946-03-19 | Ilford Ltd | Silver halide photographic emulsions |
-
1948
- 1948-05-08 GB GB12697/48A patent/GB637847A/en not_active Expired
-
1949
- 1949-05-05 US US91639A patent/US2578655A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB189600371A (en) * | 1896-01-06 | 1896-11-14 | Lembach & Schleicher | Improvements in Photographic Developers. |
| DE596105C (en) * | 1932-09-28 | 1934-04-26 | Heinz Gossler Dr | Process for adding quinine salts and other blue-black developing compounds which tend to form precipitates in the developer |
| FR768519A (en) * | 1934-02-14 | 1934-08-07 | Ig Farbenindustrie Ag | Method for determining shades of photographic developing images |
| US2397015A (en) * | 1943-02-12 | 1946-03-19 | Ilford Ltd | Silver halide photographic emulsions |
| US2395846A (en) * | 1944-06-13 | 1946-03-05 | Eastman Kodak Co | Sensitized photographic emulsion |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3446618A (en) * | 1965-11-08 | 1969-05-27 | Gaf Corp | Photographic silver halide emulsions containing trifluoromethyl - 4 - hydroxy quinoline carboxy acid salt as a stabilizer |
Also Published As
| Publication number | Publication date |
|---|---|
| GB637847A (en) | 1950-05-24 |
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