US2546642A - Light-sensitive photographic emulsion - Google Patents
Light-sensitive photographic emulsion Download PDFInfo
- Publication number
- US2546642A US2546642A US744522A US74452247A US2546642A US 2546642 A US2546642 A US 2546642A US 744522 A US744522 A US 744522A US 74452247 A US74452247 A US 74452247A US 2546642 A US2546642 A US 2546642A
- Authority
- US
- United States
- Prior art keywords
- light
- sensitive photographic
- emulsion
- styryl
- photographic emulsion
- 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
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Classifications
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02N—STARTING OF COMBUSTION ENGINES; STARTING AIDS FOR SUCH ENGINES, NOT OTHERWISE PROVIDED FOR
- F02N3/00—Other muscle-operated starting apparatus
- F02N3/02—Other muscle-operated starting apparatus having pull-cords
-
- 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
- G03C1/08—Sensitivity-increasing substances
- G03C1/28—Sensitivity-increasing substances together with supersensitising substances
Definitions
- the primary object of our invention is to provide J- an* improved light-sensitive photographic z silverhalide emulsion.
- A- more specic object is, to provide a lightsensitive photographic emulsion having a supersensitizing quality. It is known to increase the spectral sensitivity of a photographic emulsion by simultaneously using a sensitizing dyestuihwhich'.
- a still further object is to provide a photographic element comprising a support coated with l such a supersensitiaed emulsion.
- D representsnon-metallic atoms necessary to complete a heterocyclic 5- or o-membered ring
- R represents alkyl, aryl or aralkyl
- the main sensitizer and supersensitizer may simultaneously be added to the emulsion; or the coated light-sensitive emulsion already containing the main sensitizer may be bathed in a solution of the supersensitizer; or the non-sensitized emulsion layer may be bathed in a mixture of the two sensitizers. Finally, the supersensitizer may be added to the anti-stress layer or to the barite layer.
- the light-sensitive emulsion may be prepared with the help of any binder known in the photographic emulsion technique, e. g., gelatine and vinylpolymers.
- R. represents alkyl, aryl, aralkyl
- X represents a member selected from the group consisting of halogen and an acid residue
- n a positive integer
- Y represents aryl
- X represents a monovalent group selected from the group consisting of alkyl and hydrogen
- X represents an alkyl group
- D represents the nonnetallic atoms necessary-to complete a member selected from the group consisting of heterocyclic -membered and het- ⁇ erocyclic -membered rings,
- R represents alkyl, aryl, aralkyl
- X represents a member selected from the group consisting of halogen and an acid residue
- D represents the non-metallic atoms necessary to complete a member selected from the group and as a supersensitizer alphamercapto-iso valerio acid p-chloroanilide.
- D represents the non-metallic atoms necessary to 20 complete a member selected from the group 6 consisting of heterocyclic -membered and heterocyclio -rnembered rings,
- R represents alkyl, aryl, aralkyl, R and R represent alkyl
- X represents a member selected from the group consisting of halogen and an acid residue
- n represents a positive integer
Description
March 27, 1951 w. K. A. KOERBER ET AL 2,546,542
LIGHT-SENSITIVE PHOTOGRAPHIC EMULSION Filed April 28, 1947 MLLEM KAREL ANTOON KOERBER Desma MAizaA ALoyslus VAN G'OETHEM Agen Patented Mar. 27, 1951 UNITED STATES PATENT OFFICE LIGHT-SENSITIVE PHOTOGRAPHIC EMULsIoN Willem Karel Antoon Koerber, Berchem-Antwerp, and Dsir Maria"` Aloysius Van G0eth`em-,= Kontich, Belgium, assignors to'Gevaert Photo- Producten N.A V., Mortsel-Antwerp, Belgium, .a
company of Belgium- Application April 28, 1947, Serial N0. 744,522` In Germany September 5, 1941 Section 1, Public Law 690, August 8, 1946- Patent expires September' 5, 1961 6 Claims.
This invention relates to light-sensitive photographic silver halide emulsions, and more particularly to such emulsions oi increased "color sensitivity.
The primary object of our invention is to provide J- an* improved light-sensitive photographic z silverhalide emulsion.
A- more specic object is, to provide a lightsensitive photographic emulsion having a supersensitizing quality. It is known to increase the spectral sensitivity of a photographic emulsion by simultaneously using a sensitizing dyestuihwhich'.
is'called main sensitizer, and a second' sensitizing dyestui called supersensitizer. simultaneously using carbocyani es and pseudocyanines, the general sensitivity of the emulsiony is much higher than it would be theoretically by themere additional action of a sensitizer. In the photographicart,l such an increase in spectral` sensitivity is known as supersensitzing.`
A stillmore particularized object is to provide a light-sensitive photographic emulsion containing a supersensitizing combination of a styryl dye and an organic compound of the kind `disclosed hereinafter.
Further objects oi the present inventionare toprovide a method of increasing the sensitivity of. photographic emulsions sensitized with styryl' dyes, a process for sensitizing photographic einnisions with a supersensitizing combination of a styryl dye and said organic compound disclosed.
further below.
A still further object is to provide a photographic element comprising a support coated with lsuch a supersensitiaed emulsion.
Other more speciiic objects will become apparent duringfthe persual oi this.specification.
It is known to use styryl compounds for the.
optical senstizing of photographicy silverhalide emulsions.
rThough the supersensitizing action is generally .obtained by the combined use of two or more dye- -stuffs, it has already. been proposed to accomplish the supersensitizing effect bythe use of ,special cyanine dyestufls in combination with non-sensitizing organic compounds containing an amino group.
Unexpectedly, we have found that the color sensitivity of lphotograpl'lic emulsions sen'sitizt-:dl
byrm'eans of styryl compounds may be increased For instance; by
to an extraordinary extent .bythe addition to thev X represents alkyl or hydrogen; and X represents alkyl.
The present invention enables-the supersonsitizing of both silver chlorideand silver bromide emulsions sensitized by styryl compounds, improving sirnultaneousiy the stability thereof As the main sensitiaer all styryl dyestuiis may*7 beused .which correspond to the following gen eral formula:
D representsnon-metallic atoms necessary to complete a heterocyclic 5- or o-membered ring;
' R represents alkyl, aryl or aralkyl;
X represents halogen or. any acid residuegand n represents a-positive integer:
Rl N represents res1dues of secondary amines, for mstance,
\ 2- p-dimethylamino-styryl-quinoline etliiodide,
R 2-p-dimethylamino-styryl-bcnzthiazol inethiodide,
2-p-dimethylamino-styryl-beta-naphthothiazole-mctbiodido 2-p-dimethylamino-styryl-4-1netliyl-thiazole,ethiodidel 2-pV-d1methylaminostyryl-benzoxazolc benzyl bromide. According to the present invention, products capable of increasing the activity of these dyestuis are, for instance, the following;
NH-o o-oH-CEn-ornv Alpha-mercapto-n-butyric acid naphthyl amide SHv Alphmmencapto-.propionic :acid:p-itoluldide4 Alpha-mercupto-iso-valeric acid p-chloroanilide Alpha-mercapto-iso-butyric acid p-toluidde The preparation of these supersensitizers is described in Beckurts and Frederichs, Archiv der Pharmazie 253, page 161.
To carry out the method of the present invention, the main sensitizer and supersensitizer may simultaneously be added to the emulsion; or the coated light-sensitive emulsion already containing the main sensitizer may be bathed in a solution of the supersensitizer; or the non-sensitized emulsion layer may be bathed in a mixture of the two sensitizers. Finally, the supersensitizer may be added to the anti-stress layer or to the barite layer.
The light-sensitive emulsion may be prepared with the help of any binder known in the photographic emulsion technique, e. g., gelatine and vinylpolymers.
The method of our invention is illustrated by the following specic example:
A silver chloride emulsion according to Eder Handbuch III, 5th edition, i993, page 727, is prepared in the following way:
(A) 15 g. of sodium chloride,
l g. of citric acid, 20 g. of gelatine 200 cm.3 oi water; (B) 30 g. of silver nitrate,
50 cm.3 of water; (C) 20 g. of gelatine,
250 cm.3 of water.
(A) and (C) are melted at 45 C., (C) is added to (B) whilst stirring, and immediately afterwards (A) is added to (B) -i-(C). Next, 2 ein.3 oi a 0.1% 2 p dimethyl'amino styryi 4 methyl thiazole ethiodide solution are added and this mixture is allowed to ripen for one hour. Thereupon 4 0111.3 of an alcoholic solution of a 1 mercaptobutyric acid-p-toluide solution are added, and after l5 minutes the emulsion is cast. The sensitivity of this emulsion is illustrated by the accompanying drawing which is self-explanatory.
It will be apparent that while we have described our invention in preferred forms, many changes and modifications may be Ina-de without departing from the spirit o the invention dened in the following claims.
We claim: v
1. A light-sensitive photographic silver halide emulsion containing as a sensitizer 2-p-dimethylamino-styryl-i-methyl-thiazole ethiodide and as a supersensitizer alpha-rnercapto-iso-butyric acid p-toluidide. Y
2. Light-sensitive photographic silver halide emulsion containing at least one sensitizing dyestuf corresponding to the general formula:
D represents the non-metallic atoms necessary to complete'a member selected fro-m the group consisting of heterocyclic 5-nie1nbered and heteiocyclic -membered rings,
R. represents alkyl, aryl, aralkyl,
R and R" represent alkyl,
X represents a member selected from the group consisting of halogen and an acid residue, and
n represents a positive integer,
and as a supersensitizer at least one product of the general formula:
wherein Y represents aryl, X represents a monovalent group selected from the group consisting of alkyl and hydrogen, and X represents an alkyl group.
3. Light-sensitive photographic silver halide emulsion containing at least one sensitizing dyestuff corresponding to the general formula:
and as a supersensitizer alpha-mercapto n-butyric acid naphthyl amide.
4. Light-sensitive photographic silver halide emulsion containing a sensitizing ,dyestui corresponding to the general formula:
D represents the nonnetallic atoms necessary-to complete a member selected from the group consisting of heterocyclic -membered and het-` erocyclic -membered rings,
R represents alkyl, aryl, aralkyl,
R and R represent alkyl,
X represents a member selected from the group consisting of halogen and an acid residue, and
n represents a positive integer,
and as a supersensitizer alpha-mercapto propionic acid-p-toluidide.
5. Light-sensitive photographic siiver halide emulsion containing a sensitizing ,dyestuif corref spending to the general formula:
D represents the non-metallic atoms necessary to complete a member selected from the group and as a supersensitizer alphamercapto-iso valerio acid p-chloroanilide.
G. Light-sensitive photographic silver halide emulsion containing a sensitizing .dyestu corresponding to the general formula:
D represents the non-metallic atoms necessary to 20 complete a member selected from the group 6 consisting of heterocyclic -membered and heterocyclio -rnembered rings,
R represents alkyl, aryl, aralkyl, R and R represent alkyl, X represents a member selected from the group consisting of halogen and an acid residue, and n represents a positive integer,
and as a supersensitizer alpha-mercapto isobutyrc acid p-toluidide.
WILLEM KAREL ANTooN KOERBER. DSIRE' MARIA ALOYSIUS VAN GOETHEM.
REFERENCES CITED UNITED STATES PATENTS Name Date Mees Mar. 30, 1937 Number
Claims (1)
- 2. LIGHT-SENSITIVE PHOTOGRAPHIC SILVER HALIDE EMULSION CONTAINING AT LEAST ONE SENSITIZING DYESTUFF CORRESPONDING TO THE GENERAL FORMULA:
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE234132X | 1941-09-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
US2546642A true US2546642A (en) | 1951-03-27 |
Family
ID=5889850
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US744522A Expired - Lifetime US2546642A (en) | 1941-09-05 | 1947-04-28 | Light-sensitive photographic emulsion |
Country Status (6)
Country | Link |
---|---|
US (1) | US2546642A (en) |
BE (1) | BE447040A (en) |
CH (2) | CH234132A (en) |
FR (2) | FR885376A (en) |
GB (1) | GB615430A (en) |
NL (1) | NL60339C (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3457078A (en) * | 1964-03-11 | 1969-07-22 | Agfa Ag | Supersensitized silver halide emulsions |
US4105451A (en) * | 1976-12-22 | 1978-08-08 | Eastman Kodak Company | Photothermographic material, composition and process |
US5232069A (en) * | 1992-07-29 | 1993-08-03 | Mtd Products Inc. | Grease fitting and grease fitting plug for wheel hub |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10036521C2 (en) * | 2000-07-27 | 2003-12-11 | Agfa Gevaert Ag | Silver halide photographic material |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2075046A (en) * | 1932-11-04 | 1937-03-30 | Eastman Kodak Co | Photographic emulsion containing supersensitized pinacyanol |
-
0
- NL NL60339D patent/NL60339C/xx active
- BE BE447040D patent/BE447040A/xx unknown
-
1942
- 1942-08-14 CH CH234132D patent/CH234132A/en unknown
- 1942-08-19 FR FR885376D patent/FR885376A/en not_active Expired
-
1944
- 1944-02-19 FR FR53341D patent/FR53341E/en not_active Expired
- 1944-03-11 CH CH252075D patent/CH252075A/en unknown
-
1945
- 1945-09-24 GB GB24730/45A patent/GB615430A/en not_active Expired
-
1947
- 1947-04-28 US US744522A patent/US2546642A/en not_active Expired - Lifetime
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2075046A (en) * | 1932-11-04 | 1937-03-30 | Eastman Kodak Co | Photographic emulsion containing supersensitized pinacyanol |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3457078A (en) * | 1964-03-11 | 1969-07-22 | Agfa Ag | Supersensitized silver halide emulsions |
US4105451A (en) * | 1976-12-22 | 1978-08-08 | Eastman Kodak Company | Photothermographic material, composition and process |
US5232069A (en) * | 1992-07-29 | 1993-08-03 | Mtd Products Inc. | Grease fitting and grease fitting plug for wheel hub |
Also Published As
Publication number | Publication date |
---|---|
NL60339C (en) | |
FR885376A (en) | 1943-09-13 |
BE447040A (en) | |
FR53341E (en) | 1945-10-16 |
CH252075A (en) | 1947-11-30 |
GB615430A (en) | 1949-01-06 |
CH234132A (en) | 1944-09-15 |
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