US2108243A - Photographic developer - Google Patents
Photographic developer Download PDFInfo
- Publication number
- US2108243A US2108243A US90919A US9091936A US2108243A US 2108243 A US2108243 A US 2108243A US 90919 A US90919 A US 90919A US 9091936 A US9091936 A US 9091936A US 2108243 A US2108243 A US 2108243A
- Authority
- US
- United States
- Prior art keywords
- developer
- photographic
- photographic developer
- phenylenediamine
- water
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical class NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229940101006 anhydrous sodium sulfite Drugs 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- -1 ethyl- Chemical group 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 150000002832 nitroso derivatives Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- WFXLRLQSHRNHCE-UHFFFAOYSA-N 2-(4-amino-n-ethylanilino)ethanol Chemical compound OCCN(CC)C1=CC=C(N)C=C1 WFXLRLQSHRNHCE-UHFFFAOYSA-N 0.000 description 1
- FCDKGTXZKZEBPA-UHFFFAOYSA-N 2-[4-(2-hydroxyethylamino)anilino]ethanol Chemical compound OCCNC1=CC=C(NCCO)C=C1 FCDKGTXZKZEBPA-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 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
- G03C7/407—Development processes or agents therefor
- G03C7/413—Developers
- G03C7/4136—Developers p-Phenylenediamine or derivatives thereof
Definitions
- My present invention relatesjo a photographic naphthalene-Z-carboxylic acid for the production developer and more particularly to a developer of a blue color.
- One of its objects is to provide an improved Emmple 1 5 developer.
- Another object is to provide an improved developer for development in colors.
- Fur- A developer consisting of: ther objects will be seen from the detailed. specification following hereaften 10.9 grams of unsymmetrical N.N-d1-(hydroxy- Para-phenylenediamine is used as a fine-grain 60 gg gg 'gi zgggm ggfgg gfig developer and derivatives of para-phenylenediamine have been proposed as developers.
- the lat- 1000 of water ter compounds however, have not beeen introyields a 'y-value of 0.6 after minutes in a given Jerusalem into photographic practice because their emulsion.
- This invention relates to a process of photographic development in which N-hydroxyalkylg :22: g; gggi ggfi iffig figi ated para-phenylenediamines are used as developers.
- suitable compounds are un- 1000 of water symmetrical dihydroxydiethylpara-phenylenediand containing the same number of molecules of amine, methyl-hydroxyethylethyl-hydroxythe developing substance, yields in the same given ethyl-, butyl hydroxyethyl para phenylenediemulsion a 'y-value of 0.6 only after 75 minutes.
- the unsymmetrical dihydroxy-diethyl-para- 10 grams of 2-amino-5-(N-hydroxyethyl-N- butyl) -amino-toluene-dihydrochloride phenylenediamine may be made from dihydroxy- Example 3 diethyl-aniline by converting the latter into its 9,0 grams of N ethyl N hydroxyethy] p nitroso-derivative and reducing the nitrosophenylene-djamine roup.
- the developers have particularly good solubility, which is to be attributed to the hydroxyalkyl- First solution; group. Furthermore, the developers are particularly useful for development in color, since they gram N'Ndi'mydmxyethm) have the advantage over the normal alkyl-derivaene'dmmme tives that they yield purer and brighter colors.
- Example 4 For the purpose of development in color there second solution; may be added to the developer besides the devel- J oping substance, substances which have a tendgram of phenyl-methyl-pyrazolone ency to produce dyestuffs during the development grams of anhydrous Sodium b nate by oxidation of the developer, for instance, a de- 100 of Waterrivative of acylacetic acid ester for the produc- Example 5 tion of a yellow color, pyrazolones for the production of a red color, and a derivative of l-hydroxy- First solution:
- a photographic developer comprising an N- hydroxyalkylated'p-phenylenediamine.
- a photographic developer comprising an N- hydroxyalkylated p-phenylenediamine and a compound capable of forming a dye with the oxidation products or the developer.
- a photographic developer comprising unsymmetrical N.N di-(hydroxyethyl) -p-phenylenediamine.
- a photographic developer comprising N- ethyl-N-hydroxyethyl-p-phenylenediamine, anhydrous sodium sulfite, potassium bromide and water.
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)
Description
Patented Feb.15,1938 1 2,103,243-
UNITED STATES PATENT OFFICE 2,108,243 PHOTOGRAPHIC DEVELOPER Bruno Wendt, Dessau, Germany, assignor to Asia Ansco Corporation, Binghamton, N. Y., a. corporation or New York No Drawing. Application July 16, 1936, Serial No. 90,919. In Germany July 23, 1935 5 Claims. (CI. 95-88) My present invention relatesjo a photographic naphthalene-Z-carboxylic acid for the production developer and more particularly to a developer of a blue color.
for development in colors. The following examples illustrate the invention:
One of its objects is to provide an improved Emmple 1 5 developer. Another object is to provide an improved developer for development in colors. Fur- A developer consisting of: ther objects will be seen from the detailed. specification following hereaften 10.9 grams of unsymmetrical N.N-d1-(hydroxy- Para-phenylenediamine is used as a fine-grain 60 gg gg 'gi zgggm ggfgg gfig developer and derivatives of para-phenylenediamine have been proposed as developers. The lat- 1000 of water ter compounds, however, have not beeen introyields a 'y-value of 0.6 after minutes in a given duced into photographic practice because their emulsion. On the other hand, a developer conspeed in developing is relatively low. sisting of: 5 This invention relates to a process of photographic development in which N-hydroxyalkylg :22: g; gggi ggfi iffig figi ated para-phenylenediamines are used as developers. Examples of suitable compounds are un- 1000 of water symmetrical dihydroxydiethylpara-phenylenediand containing the same number of molecules of amine, methyl-hydroxyethylethyl-hydroxythe developing substance, yields in the same given ethyl-, butyl hydroxyethyl para phenylenediemulsion a 'y-value of 0.6 only after 75 minutes.
amine, as well as the corresponding toluidines. Also fi-y-dlhydroxy propyl para phenylenedi- Example 2 amines, such as the diamine itself and its alkyl- A developer consisting of:
25 derivatives. These compounds are obtainable by known methods from the corresponding aniline derivatives, the latter being converted into the nitroso-derivative and the nitroso-group be- 10 grams of i ing then reduced; or by coupling the hydroxygrams of caustlc soda alkyl-aniline derivative with an azo-component, 1000 of water for instance diazotized sulianilic acid, to make an yields green picture, whereas t known azo-dyestufi which is then reduced in the usual velopers having dibromooresol as a constituent manneryield only a blue-green color.
The unsymmetrical dihydroxy-diethyl-para- 10 grams of 2-amino-5-(N-hydroxyethyl-N- butyl) -amino-toluene-dihydrochloride phenylenediamine may be made from dihydroxy- Example 3 diethyl-aniline by converting the latter into its 9,0 grams of N ethyl N hydroxyethy] p nitroso-derivative and reducing the nitrosophenylene-djamine roup. Develope s ade wit t s mp 60.0 grams of anhydrous sodium sulfite velop about three times more quickly than that 05 gllam of potassium b d 40 made from non-substituted para-phenylenedi- 1000 cm f water amine and also yield very fine-grain negatives.
The developers have particularly good solubility, which is to be attributed to the hydroxyalkyl- First solution; group. Furthermore, the developers are particularly useful for development in color, since they gram N'Ndi'mydmxyethm) have the advantage over the normal alkyl-derivaene'dmmme tives that they yield purer and brighter colors. '100 of water Example 4 For the purpose of development in color there second solution; may be added to the developer besides the devel- J oping substance, substances which have a tendgram of phenyl-methyl-pyrazolone ency to produce dyestuffs during the development grams of anhydrous Sodium b nate by oxidation of the developer, for instance, a de- 100 of Waterrivative of acylacetic acid ester for the produc- Example 5 tion of a yellow color, pyrazolones for the production of a red color, and a derivative of l-hydroxy- First solution:
1.0 gram oi N.N-di-(hydroxyethyi) -p-pheny1- enediamine 100 cc. of water.
Second solution:
0.9 gram of o-phenyl-phenol 0.4 gram of caustic soda. 100 cc. of water.
In Examples 4 and 5 the two, solutions are mixed 10 before use.
What I claim is: 1. A photographic developer comprising an N- hydroxyalkylated'p-phenylenediamine.
2. A photographic developer comprising an N- hydroxyalkylated p-phenylenediamine and a compound capable of forming a dye with the oxidation products or the developer.
3. A photographic developer comprising unsymmetrical N.N di-(hydroxyethyl) -p-phenylenediamine.
4. A photographic developer comprising N- ethyl-N-hydroxyethyl-p-phenylenediamine, anhydrous sodium sulfite, potassium bromide and water.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF3216D DE889549C (en) | 1935-07-24 | 1935-07-24 | Photographic developer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2108243A true US2108243A (en) | 1938-02-15 |
Family
ID=27815498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US90919A Expired - Lifetime US2108243A (en) | 1935-07-24 | 1936-07-16 | Photographic developer |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US2108243A (en) |
| AT (1) | AT151322B (en) |
| BE (1) | BE416619A (en) |
| DE (1) | DE889549C (en) |
| FR (1) | FR808377A (en) |
| GB (1) | GB460580A (en) |
| NL (1) | NL44835C (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2596978A (en) * | 1947-09-17 | 1952-05-20 | Searle & Co | 8-hydroxy-1, 2, 3, 4-tetrahydroquinoline as a silver halide developer |
| US2611785A (en) * | 1952-09-23 | N-substituted x | ||
| US3884627A (en) * | 1971-10-04 | 1975-05-20 | Clairol Inc | Oxidative hair dye compositions |
| US5380625A (en) * | 1992-02-05 | 1995-01-10 | Fuji Photo Film Co., Ltd. | Method for processing silver halide color photographic materials comprising particular dye couplers using particular developers |
-
0
- NL NL44835D patent/NL44835C/xx active
- BE BE416619D patent/BE416619A/xx unknown
-
1935
- 1935-07-24 DE DEF3216D patent/DE889549C/en not_active Expired
- 1935-07-29 GB GB21492/35A patent/GB460580A/en not_active Expired
-
1936
- 1936-06-24 AT AT151322D patent/AT151322B/en active
- 1936-07-16 US US90919A patent/US2108243A/en not_active Expired - Lifetime
- 1936-07-18 FR FR808377D patent/FR808377A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2611785A (en) * | 1952-09-23 | N-substituted x | ||
| US2596978A (en) * | 1947-09-17 | 1952-05-20 | Searle & Co | 8-hydroxy-1, 2, 3, 4-tetrahydroquinoline as a silver halide developer |
| US3884627A (en) * | 1971-10-04 | 1975-05-20 | Clairol Inc | Oxidative hair dye compositions |
| US5380625A (en) * | 1992-02-05 | 1995-01-10 | Fuji Photo Film Co., Ltd. | Method for processing silver halide color photographic materials comprising particular dye couplers using particular developers |
Also Published As
| Publication number | Publication date |
|---|---|
| DE889549C (en) | 1953-09-10 |
| BE416619A (en) | |
| FR808377A (en) | 1937-02-04 |
| NL44835C (en) | |
| GB460580A (en) | 1937-01-29 |
| AT151322B (en) | 1937-11-10 |
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