US2186852A - Photographic silver halide emulsions - Google Patents
Photographic silver halide emulsions Download PDFInfo
- Publication number
- US2186852A US2186852A US176058A US17605837A US2186852A US 2186852 A US2186852 A US 2186852A US 176058 A US176058 A US 176058A US 17605837 A US17605837 A US 17605837A US 2186852 A US2186852 A US 2186852A
- Authority
- US
- United States
- Prior art keywords
- silver halide
- dyestufl
- color
- acid
- silver
- 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
- 229910052709 silver Inorganic materials 0.000 title description 29
- 239000004332 silver Substances 0.000 title description 29
- 239000000839 emulsion Substances 0.000 title description 26
- -1 silver halide Chemical class 0.000 title description 24
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 13
- 238000009792 diffusion process Methods 0.000 description 12
- 239000000975 dye Substances 0.000 description 11
- 235000007586 terpenes Nutrition 0.000 description 8
- 239000007859 condensation product Substances 0.000 description 7
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 238000004061 bleaching Methods 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- BEWYHVAWEKZDPP-UHFFFAOYSA-N bornane Chemical group C1CC2(C)CCC1C2(C)C BEWYHVAWEKZDPP-UHFFFAOYSA-N 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- JEIWMMMVZOQQHT-UHFFFAOYSA-N 1,2,2-trimethylcyclopentane-1,3-dicarbonyl chloride Chemical compound CC1(C)C(C(Cl)=O)CCC1(C)C(Cl)=O JEIWMMMVZOQQHT-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- JQKDHRYLTYOICY-UHFFFAOYSA-N 2-amino-3-naphthalen-1-yl-3-oxopropanoic acid Chemical compound C1=CC=C2C(C(=O)C(C(O)=O)N)=CC=CC2=C1 JQKDHRYLTYOICY-UHFFFAOYSA-N 0.000 description 1
- FFSGLKWXIJLRST-UHFFFAOYSA-N 2-amino-3-oxo-3-phenylpropanoic acid Chemical compound OC(=O)C(N)C(=O)C1=CC=CC=C1 FFSGLKWXIJLRST-UHFFFAOYSA-N 0.000 description 1
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- BQBWUVWMUXGILF-UHFFFAOYSA-N 2-anthrol Chemical compound C1=CC=CC2=CC3=CC(O)=CC=C3C=C21 BQBWUVWMUXGILF-UHFFFAOYSA-N 0.000 description 1
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- JCUYNPHEESTECG-UHFFFAOYSA-N 3-amino-6-(4-aminophenyl)benzene-1,2-disulfonic acid Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C(S(O)(=O)=O)=C1S(O)(=O)=O JCUYNPHEESTECG-UHFFFAOYSA-N 0.000 description 1
- HXLBZMMJEVSVKA-UHFFFAOYSA-N 4,7,7-trimethylbicyclo[2.2.1]heptan-2-amine Chemical compound C1CC2(C)CC(N)C1C2(C)C HXLBZMMJEVSVKA-UHFFFAOYSA-N 0.000 description 1
- WNRVXVWPXKDOEB-UHFFFAOYSA-N 4-methylpyrazol-3-one Chemical compound CC1=CN=NC1=O WNRVXVWPXKDOEB-UHFFFAOYSA-N 0.000 description 1
- WDODWBQJVMBHCO-UHFFFAOYSA-N 7,7-dimethyl-3-oxobicyclo[2.2.1]heptane-4-carboxylic acid Chemical compound C1CC2(C(O)=O)C(=O)CC1C2(C)C WDODWBQJVMBHCO-UHFFFAOYSA-N 0.000 description 1
- LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- XETQTCAMTVHYPO-UHFFFAOYSA-N Isocamphan von ungewisser Konfiguration Natural products C1CC2C(C)(C)C(C)C1C2 XETQTCAMTVHYPO-UHFFFAOYSA-N 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- 244000154870 Viola adunca Species 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- XIWMTQIUUWJNRP-UHFFFAOYSA-N amidol Chemical compound NC1=CC=C(O)C(N)=C1 XIWMTQIUUWJNRP-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229930006742 bornane Natural products 0.000 description 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 150000002148 esters Chemical class 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- CFJYNSNXFXLKNS-UHFFFAOYSA-N p-menthane Chemical group CC(C)C1CCC(C)CC1 CFJYNSNXFXLKNS-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical class ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 230000001131 transforming effect Effects 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
- G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
- G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
- G03C7/32—Colour coupling substances
- G03C7/3212—Couplers characterised by a group not in coupling site, e.g. ballast group, as far as the coupling rest is not specific
Definitions
- This invention has for an object to provide a layers containing a dyestufl component made fast to diffusion by the introduction into its molecule of a radical according to this invention.
- the present invention is based on a process in which especially useful dyestuil formers last todiflusion are obtained by introducing as a substituent into a dyestufl component a compound or derivative of thecyclic menthane group.
- Dyestufl components into which these groups may be introduced are for example aand 18- hydroxynaphthoic acids, 2.3-hydroxyanthracene ,carboxylic acid, salicylic acid, hydroxy-fiuorene carboxylic acid, 2.3-hydi'oxycarbazole carboxylic acid, a-naphthol aldehyde, 'aminophenyl methyl pyrazolone, aromatic amines, aminonaphthols.
- aminonaphthol carboxylic acids aminonaphthol sulfonic acids, aminophenols, aminobenzoyl acetic acid ester arylides, aminonaphthoyl acetic acid ester arylides, acylacetic acid ester amino- I 'arylides.
- the dyestufl components used in the invention may be added to the emulsion'at any point ofits production.
- the silver halide emulsions thus obtained are especially suitable for the purpose of color photography and may be made into layers in known manner, being applied superimposed on each other on one or both sides of a support. They may be sensitized for various regions' of the spectrum. Emulsions may be applied, however, in another manner, for example the several sensitized emulsions having the different dyestufl formers may be brought on to the support in the form of small particles.
- the emulsion layers used in the invention may be combined with other layers in which the color picture is produced by a different process, for example by mordant dyeing or by toning. Furthermore, the
- emulsion layers of the invention may be combined with other layers which contain other dyestufl formers fast to diffusion as described in the U. S. Patent applications cited hereunder.
- the colored pictures may be produced in varioils manners, for example bythe processes of U. S. Patents 2,179,228; 2,179,238; 2,179,244 and 2,178,612 and U. S. applications Ser. No. 94,340, filed August 5, 1936, Ser. No. 141,093 filed May 6, 1937, Ser. No. 159,518 filed August 17, '1937, Ser. No. 164,499 filed September 18, 1937 and Ser. No. 171,705 filed October 29, 1937.
- a diazo compound such as a carbonic acid solution of tetrazotized benzidine disulfonic acid.
- azotate silver picture and may be subsequently immersed in a dilute acid solution, whereby a yellow picture is produced consisting of the amdyestuif para camphoryl-aminobenzoyl-acetylaniline-4carboxylic acid azo-p-naphthalene.
- the film is then treated with a silver bleaching out bath, i. e. that described in British Patent 401,340 to produce the dye image.
- a silver bleaching out bath i. e. that described in British Patent 401,340 to produce the dye image.
- the exposed emulsion layers may be-developecl by a simple color forming development or by a reversal development as described in U. 53. Patent 2,179,234.
- the picture may be produced in multi-layer material, each layer containing one of said dyestufl components, by exposing the material, developing to black and white, in for instance Amidol, dissolving silver from the negative so produced by bleaching in for example a chromic acid bath, forming images in the remaining silver halide, developing in a developer such as is, used above, iorming silver halideimages .by treatment in a bleaching bath, 1. e.
- the exposed emulsiom may be developed in a solution 0! para-aminodimethyl-aniline. alkaline with sodium carbonate, in which case a In the produc-,
- the dyestufi' former fast to diffusion thus obtained is added to a silver halide emulsion which is then converted for example with the aid or'the' silver antidiazotate process into a picture the color of which varies with the antidiazotate se lected. For instance, if the antidiazotate is made from dianisidine there is obtained a'blue violet picture. When the anti-diazotate used is from para-nitraniline pictures of red tints are obtained.
- the condensation product has the following formula aiiii obtained.
- this dyestufl former is chiefly suitable for producing yellow tints.
- a silver halide emulsion for color photography containing a dyestufi component fast to diffusion, said dyestuff component being capable of forming a dye with the oxidation product of a developer and containing inits molecule a radical having substantially the chemical structure of a saturated bicyclic terpene having a dimethyl ture of a saturated bicyclic terpene having a dimethyl substituted carbon atom as the bridge common to the rings, and another radical capable of preventing diffusion of said dyestufl component.
- a silver halide emulsion for color photography containing a dyestuff component fast to diflusion, said dyestufl component being capable of forming a dye with the oxidation product of a developer and containing in its molecule a molecule a radical having substantially the chemical structure of a saturated bicyclic terpene having a dimethyl substituted carbon atom as the bridge common to the rings.
- a silver halide emulsion for color photography containing a dyestu'ff component fast to diffusion, said dyestuif component being capable of forming a dye with the oxldationproductof of forming a dye with the oxidation product of V a developer, and containing in its molecule .an
- a developer and containing in its molecule a radical having substantially the chemical structure of a saturated bicycfic terpene having a dimethyl substituted carbona'tom as the bridge common to the rings, said terpene radical being linked to the dyestuif forming radical by means of an acid amide linking;
- a silver halide emulsion for color photography containing a dyestuif component fast to diffusion, said dyestuif component being capable acid radical substituted by an amine of a saturated bicyclic terpene having a dimethyl substituted carbon atom as the bridge common to the rings.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEI0056651 | 1936-12-18 |
Publications (1)
Publication Number | Publication Date |
---|---|
US2186852A true US2186852A (en) | 1940-01-09 |
Family
ID=7194405
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US176058A Expired - Lifetime US2186852A (en) | 1936-12-18 | 1937-11-23 | Photographic silver halide emulsions |
Country Status (3)
Country | Link |
---|---|
US (1) | US2186852A (enrdf_load_stackoverflow) |
BE (1) | BE425269A (enrdf_load_stackoverflow) |
FR (1) | FR830926A (enrdf_load_stackoverflow) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2712995A (en) * | 1949-07-04 | 1955-07-12 | Agfa Ag | Process for the direct production of positive photographic images |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE759642C (de) * | 1941-07-01 | 1952-10-27 | Ig Farbenindustrie Ag | Verfahren zur Herstellung von photographischen Farbenbildern |
-
0
- BE BE425269D patent/BE425269A/xx unknown
-
1937
- 1937-11-23 US US176058A patent/US2186852A/en not_active Expired - Lifetime
- 1937-12-17 FR FR830926D patent/FR830926A/fr not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2712995A (en) * | 1949-07-04 | 1955-07-12 | Agfa Ag | Process for the direct production of positive photographic images |
Also Published As
Publication number | Publication date |
---|---|
BE425269A (enrdf_load_stackoverflow) | |
FR830926A (fr) | 1938-08-12 |
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