US2197311A - Color forming developer and process of color development - Google Patents
Color forming developer and process of color development Download PDFInfo
- Publication number
- US2197311A US2197311A US273560A US27356039A US2197311A US 2197311 A US2197311 A US 2197311A US 273560 A US273560 A US 273560A US 27356039 A US27356039 A US 27356039A US 2197311 A US2197311 A US 2197311A
- Authority
- US
- United States
- Prior art keywords
- color
- regard
- residue
- atoms
- hydroxyl group
- 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
- 238000011161 development Methods 0.000 title description 16
- 238000000034 method Methods 0.000 title description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 30
- 239000003795 chemical substances by application Substances 0.000 description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 22
- -1 4-(2hydroxy-3',5-dibromobenzyl)-3 methyl phenol Chemical compound 0.000 description 17
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 16
- 230000018109 developmental process Effects 0.000 description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 13
- 125000003118 aryl group Chemical group 0.000 description 10
- 150000004982 aromatic amines Chemical class 0.000 description 9
- 229910052709 silver Inorganic materials 0.000 description 8
- 239000004332 silver Substances 0.000 description 8
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000975 dye Substances 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 5
- 125000001246 bromo group Chemical group Br* 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000006286 dichlorobenzyl group Chemical group 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229960003742 phenol Drugs 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- KTHUKEZOIFYPEH-UHFFFAOYSA-N 1-benzylnaphthalene Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=CC=CC=C1 KTHUKEZOIFYPEH-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
- FLROJJGKUKLCAE-UHFFFAOYSA-N 3-amino-2-methylphenol Chemical class CC1=C(N)C=CC=C1O FLROJJGKUKLCAE-UHFFFAOYSA-N 0.000 description 1
- 101100491995 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) aro-1 gene Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241001208007 Procas Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000006157 aromatic diamine group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000001046 green dye Substances 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
- 229940100630 metacresol Drugs 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000001429 visible spectrum 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
- 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
- G03C7/34—Couplers containing phenols
- G03C7/346—Phenolic couplers
Definitions
- Patented Apr. 16, 1940 UNITED STATES PATENT OFFICE No Drawing. Application May 13, 1939, Serial No. 273,560. In Great Britain May 23, 1938 16 Claims.
- This invention relates to photographic color development and to processes of color develop-- ment for use in connection with color' photography.
- colored photographic images may be formed by using a developer which forms a colored and insoluble oxidation product during development, the colored product thus formed coloring the gelatine adjacent to the silver grains of the silver image. It is also known that a colored image may be formed by adding to certain developer solutions a com-'- pound which couples during development with the oxidation product of the developing agent and forms a coloring substance which is deposited adjacent to the developed silver grains.
- the present invention is based on the discovery of a new group of colorcouplers which in general satisfy the above requirements, and which are hydroxy-derivatives of diphenylmethane or, phenyl-naphthyl-methane, in which both of the aromatic nuclei include at least one hydroxyl group.
- Such bodies have the following general formula: i
- X' Phenyl or naphthyl residue with; one bydroxyl group in the ortho or para position with regard to CH1, the remaining neatoms of the phenyl or naphthyl residue 'can be substituted or not by halogens, alkyl-, aryl-, or .aralkyl-groups, alkoxy, amino, or nitrogroups and in the case ofa phenyl residue or the ring of a n'aphthyl-reaidue, which ring contains already an OH-groupin the para-position to the OH: group, one or more otthe remainingH-atomsmaybesubsti the corresponding number of OH
- These color couplers form in general blue or blue-green colors on coupling with the oxidation product of aromatic. amino developing agents during the
- the present invention consists in new or imaddition to an aromatic amino-developing agent a color coupler as above defined.
- the present invention also includes a new or improved process or method of color development which,comprises developing a latent photographic image by means of an aromatic amino-developer, in the presence of a color coupler as above defined, the silver image which is formed during development being eliminated so that a clear and transparent color image remains.
- the present invention further. includes photographic elements having at least one layer containing a clear transparent image composed essentially of the product resultingfrom the coupling in situ during development of a color coupler as above defined with the oxidation product of an aromatic amino developing agent.
- Typical example& 015- suitable couplers within the scope of the invention are:
- aromatic amino compounds which may be used as developing agents in the present invention include the mono-d1 and tri-amino aryl compounds.
- mono-amino developing agents may be mentioned amino-phenols and amino-cresols and their halogen derivatives and amino-naphthols.
- Thedevelopin'a agents mostly used and giving 90 thebeetresultsin connectionwiththepresent invention are the aromaticortho and para diamines, suchas para-phenylenediamineand its substitution products. These developing agents may be substituted in one amino group or 'in thee5 ring orin-both, iorming compo mds such as:-
- the invention is in no way limited to the use of the color coupler in the developing solution itself.
- the other ingredients or the color forming baths, containing chiefly the aromatic amino developing agent, may be applied later, during the developing process, as
- the present invention may be utilized in the formation of colored photographic images on 7 plates or papers as well as on film employing gelatine or other carrier for the silver halide.
- developing process may be used for the develop- 4 .ing of photographic material, provided with one or more light sensitive layers, which are applied on one side or on both sides or the support.
- the silver formed during the developing procas may be eliminated.
- a bath must be used, however, which does not destroy the dye.
- a bath consisting of a solution in water of potassium ierricyanide and sodium thiosulphate easily eliminates the silver without destroying the dye, leaving a pure dye image.
- the newcolor couplers have decided advantages when compared with those known hitherto. They can be produced easily and they form with paradiamino developers blue and blue/green dyes which are practically insoluble in water and in photographic baths. Their principal and most surprising quality is that their capacity of absorption is very small in the blue and'blue/green part of the visible spectrum. They have, turthermore, the interesting property that, it added 0 direct to the developing bath without being previously dissolved in organic solvents, they give intense coloration.
- Color forming developer comprising an am- 5 matic amine developing agent and a color coupler consisting of a diaryl methane having following general formula:
- a matic amine developing agent and a color coupler consisting of a diaryl methane having the following general formula:
- Y a phenyl residue with one hydroxyl group in" a position other than the meta position with regard to CH2 and where at least two of the remaining I-I-atoms in the ring are replaced by two halogen atoms
- X' a naphthyl residue with one hydroxyl group in a position other than 88- with regard to CH2.
- Color forming developer comprising an aro- I matic amine developing agent and a color coupler consisting of a diaryl methane havinglthe 4 following general formula;
- Color forming developer comprising an aromatic amine developing agent and a color coupler consisting of a diaryl methane having the 6 following general formula:
- X a phenylresidue with one group a position other than the meta position with regard and where at least two of the remainingH-atomsintheringarereplaced.
- X' a phenyl residue with one hydroxyl group I 70 in a position para with regard to'CH: and at least one of the remaining H-atoms of the residue substituted byan OH group'.
- Color forming developer comprising an arc- 7 matic amine developing agent and a color'coupler position the meta position where consisting of a diaryl methane having the following general formula:
- X a phenyl residue with one hydroxylgroup in a position other than the meta position with regard to CH2 and where at least two of the remaining H-atoms in the ring are replaced by two bromine atoms 1o
- X' an aryl residue with one hydroxyl group in a position other than the meta position with regard to CH2.
- Color forming developer comprising an aromatic amine developing agent and a color coupler consisting of a diaryl methane having the following. general formula;
- Color forming developer comprisingan aromatic amine developing agent which is a compound of the aromatic diamine group and a color coupler consisting of a diaryl methane having the following general formula:
- X a phenyl residue with one hydroxyl group in a position other than the meta position with regard to CH2 and where at least two of the remaining'H-atoms inthe ring are re- 0 placed by two halogen atoms
- X' an aryl residue with one hydroxyl group in a position other than the meta position with regard to CH2.
- Color forming developer comprising an aro- 4 matic amine developing agent which is a substituted phenylene diamine, and a, color coupler consisting of a diaryl methane having the following general formula:
- Y X a phenyl residue with one' hydroxyl group in a position other-than the meta position with regard to CH2 and where at least two of the regard to CH2.
- X-CHa-X' X a phenyl residue with one hydroxyl group in a position other than the meta position with regard to CH2 and where at least two 'of the remaining'H-atoms in the ring are replaced by two halogenatoms 15- x-crnhx'. as-
- X' an aryl residue with one hydroxyl group in a position other than the meta position with regard to CH2 andat least one H -atom of the residue substituted by an individual included in the group alkyl aryl aralkyl alkoxy amino or nitro halogens and hydroxyl.
- x a phenyl residue with one hydroxyl group in a position other than the meta'posltion with regard to CH2 and where at least two of the remaining H-atoms in the ring are replaced by two halogen atoms
- X' a phenyl residue with one hydroxyl group in a position para with regard to CH2 and at least one of the remaining H-atomsof the residue substituted by .an' OH group.
- X a phenyl residue with one hydroxyl group in a position other than the meta position with regard to CH2 and where at least two of the remaining H-atoms in the ring are replaced by two bromine atoms
- X' an aryl residue with one hydroiqrl group in a position other than the meta position to the action of a color forming developer containing an aromatic amine developing agent and a color coupler consisting of a diaryl methane haviiig the following general formula:
- X' a phenyl residue with one hydroxyl group in a position para with regard to CH2 and at least one of the remaining H-atoms of the residue substituted by an OH group.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB15383/38A GB506224A (en) | 1938-05-23 | 1938-05-23 | Improvements in and relating to colour forming developers and processes of colour development |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2197311A true US2197311A (en) | 1940-04-16 |
Family
ID=10058184
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US273560A Expired - Lifetime US2197311A (en) | 1938-05-23 | 1939-05-13 | Color forming developer and process of color development |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2197311A (enrdf_load_stackoverflow) |
| BE (1) | BE434126A (enrdf_load_stackoverflow) |
| FR (1) | FR854606A (enrdf_load_stackoverflow) |
| GB (1) | GB506224A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2417514A (en) * | 1940-09-23 | 1947-03-18 | Spectrum Products Company Inc | Method and means for producing colored photographic images |
| US2476008A (en) * | 1945-09-28 | 1949-07-12 | Eastman Kodak Co | p-hydroxy benzyl alcohol couplers for color photography |
| US2541727A (en) * | 1947-12-17 | 1951-02-13 | Gen Analine & Film Corp | Diazotypes containing aldehyde reaction products of dihydroxy aryl compounds |
| US3880661A (en) * | 1971-12-29 | 1975-04-29 | Eastman Kodak Co | Silver halide emulsion containing acylamidophenol photographic couplers |
-
0
- BE BE434126D patent/BE434126A/xx unknown
-
1938
- 1938-05-23 GB GB15383/38A patent/GB506224A/en not_active Expired
-
1939
- 1939-05-11 FR FR854606D patent/FR854606A/fr not_active Expired
- 1939-05-13 US US273560A patent/US2197311A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2417514A (en) * | 1940-09-23 | 1947-03-18 | Spectrum Products Company Inc | Method and means for producing colored photographic images |
| US2476008A (en) * | 1945-09-28 | 1949-07-12 | Eastman Kodak Co | p-hydroxy benzyl alcohol couplers for color photography |
| US2541727A (en) * | 1947-12-17 | 1951-02-13 | Gen Analine & Film Corp | Diazotypes containing aldehyde reaction products of dihydroxy aryl compounds |
| US3880661A (en) * | 1971-12-29 | 1975-04-29 | Eastman Kodak Co | Silver halide emulsion containing acylamidophenol photographic couplers |
Also Published As
| Publication number | Publication date |
|---|---|
| FR854606A (fr) | 1940-04-19 |
| BE434126A (enrdf_load_stackoverflow) | |
| GB506224A (en) | 1939-05-24 |
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