US1516161A - Nathan sulzberger - Google Patents
Nathan sulzberger Download PDFInfo
- Publication number
- US1516161A US1516161A US1516161DA US1516161A US 1516161 A US1516161 A US 1516161A US 1516161D A US1516161D A US 1516161DA US 1516161 A US1516161 A US 1516161A
- Authority
- US
- United States
- Prior art keywords
- developer
- amin
- hydroxyl
- phenyl
- photographic
- 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
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulphite Substances [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 62
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N benzohydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 36
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 34
- 235000010265 sodium sulphite Nutrition 0.000 description 32
- 239000011780 sodium chloride Substances 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- CKRZKMFTZCFYGB-UHFFFAOYSA-N Phenylhydroxylamine Chemical compound ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 description 24
- -1 citric Chemical class 0.000 description 22
- 150000003839 salts Chemical class 0.000 description 20
- 125000003118 aryl group Chemical group 0.000 description 18
- 229960004337 hydroquinone Drugs 0.000 description 18
- 239000004615 ingredient Substances 0.000 description 18
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 18
- IOLCXVTUBQKXJR-UHFFFAOYSA-M Potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 16
- AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 16
- 150000007524 organic acids Chemical class 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 12
- AERWWAYEYYMAPN-UHFFFAOYSA-N oxalic acid;N-phenylhydroxylamine Chemical compound OC(=O)C(O)=O.ONC1=CC=CC=C1 AERWWAYEYYMAPN-UHFFFAOYSA-N 0.000 description 12
- 239000001187 sodium carbonate Substances 0.000 description 12
- 229910000029 sodium carbonate Inorganic materials 0.000 description 12
- 239000000463 material Substances 0.000 description 10
- 235000005985 organic acids Nutrition 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 230000001627 detrimental Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000006011 modification reaction Methods 0.000 description 4
- 235000006408 oxalic acid Nutrition 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 230000001681 protective Effects 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-Benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- GQIAUSRLTQPZIZ-UHFFFAOYSA-M S(=O)([O-])O.[Na+].C(C(=O)O)(=O)O Chemical compound S(=O)([O-])O.[Na+].C(C(=O)O)(=O)O GQIAUSRLTQPZIZ-UHFFFAOYSA-M 0.000 description 2
- HIQMHBJNMONOJZ-UHFFFAOYSA-M S(=O)([O-])O.[Na+].C(C(=O)O)(=O)O.C1(=CC=CC=C1)NO Chemical compound S(=O)([O-])O.[Na+].C(C(=O)O)(=O)O.C1(=CC=CC=C1)NO HIQMHBJNMONOJZ-UHFFFAOYSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 230000002708 enhancing Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000000979 retarding Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
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
- G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
- G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
- G03C5/29—Development processes or agents therefor
- G03C5/305—Additives other than developers
Definitions
- the present invention relates to improved photographic developers of a stable charactercontaining an aromatic hydroxyl-amin substance, and more particularly a salt of phenyl-hydroxyl-amin or its homologues or derivatives, etc., with an organic acid.
- Beta-phenyl-hydroxyl-amin itself and certain of its derivatives are unstable in solution and particularly in alkaline solution, and even in a dry state, and, without special treatment, are not available for use as photographic developers.
- the present invention relates to photographic developers which are relatively stable in character.
- the new photographic developers contain or are made from salts of the hydroxyl-amins and more partic-' ularly salts with organic acids.
- oxalic acid instead of combining the phenyl-hydroxylamin with oxalic acid. it can be combined with other organic acids such as citric, formic lactic, pyrogallic, tannic, etc, or in general Serial No. 491,296.
- acids which have no detrimental action when combined with the phenyl-hydroxyl-amin, that is, no action detrimental for use as photographic developers.
- the acids employed should not of course be of such a character that the action of the developer will be destroyed or detrimentally influenced to an objectionable extent; acids enhancing the developing qualities are of particular value.
- the new photographic developers contain the hydroxyl-amin substancewith other suitable ingredients, including, if desired, also such as will tend to prevent or retard any too rapid'or objectionable oxidation of the hydroxyl-amin substance itself, particularly in the alkaline solution.
- compositions well adapted for use for photographic developing purposes :
- Phenyl-hydroxyl-amin oxalate- 20 grainso (as above described) Sodium carbonate (anhydrous) 600 grains. Potasiurn bromide (crystalline) 4 graiirs In using this developer it can be diluted with water to the desired extent, and may then be used for developing films in much the usual manner, but with added advantage to the developing process and to the result produced.
- salts of phenyl-hydroxylamin itself with organic acids
- suitable compounds or salts of its homolo-gues or of other aromatic hydroxyl-amins such as naphtyl-hydroxyl-amin, etc., and their derivatives may be employed.
- these salts can be kept for considerable periods of time and used in a dry state when desired, or they can be combined with other dry ingredients of the developer and the composite developer then added to water, or to other solution for use.
- the developer may thus be put up in tablet form, etc., either pure or mixed.
- the phenyl-hydroxyl-amin oxalate is compounded With sodium sulfite and sodium carbonate as well as with other developer ingredients, for example, hydroquinone and potassium bromide.
- the sodium sulfite contributes to the developer composition and also has a protective influence upon the alkaline solution of the hydroxylamin substances, Other substances having similar action may be employed.
- a photographic developer containing an organic acid saltof an aromatic hydoxylamin together with other developer ingre' proliferatives 1.
- a photographic developer containing an organic acidg,.salt of phenyl-hydroxylamin together with sodium sulfite and other developer ingredients.
- a photographic developer comprising an alkaline solution containing an organic acid salt of an aromatic hydroxyl-amin, and sodium sulfite.
- a photographic developer comprising an alkaline solution containing an organic acid salt of phenyl-hydroxyl-amin and sodium sulfite.
- a photographic developer comprising an aqueous solution of phenyl-hydroxylamin oxalate, together with sodium sulfite and sodium carbonate.
- a photographic developer comprising a solution in water of phenyl-hydroxylamin oxalate sodium sulfite, sodium carbonate, and hydroquinone.
- a photographic developer comprising a solution in water of phenyl-hydroxylamin, oxalate sodium sulfite, sodium carbonate, potassium bromide, and hydroquinone.
- a photographic developer containing in a dry state a stable aromatic hydroxylamin compound containing in a dry state a stable aromatic hydroxylamin compound.
- a photographic developer comprising a stable aqueous solution of an aromatic hydroxyl-amin compound together with sodium sulfite, hydro-quinone and sodium carbonate.
- a photographic developer comprising a stable aqueous solution of an aromatic hydroxyl-amin compound together with a protective ingredient preventing objectionable too rapid oxidation of such compound.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Description
Patent Nov. 18, 1924.
NATHAN S'ULZIBERGER, OF NEW YORK, N. Y.
PHOTOGRAPHIC DEVELOPER.
Original application filed December 18, 1918, Serial No. 267,409 Divided and this application filed August 10, 1921.
county of New York, State of New York,
have invented certain new and useful Improvements in Photo aphic Developers; and I do hereby declare the following to be a full, clear, and exact description of the invention, such as will enable others skilled in the art to which it appertains to make and use the same.
The present invention relates to improved photographic developers of a stable charactercontaining an aromatic hydroxyl-amin substance, and more particularly a salt of phenyl-hydroxyl-amin or its homologues or derivatives, etc., with an organic acid.
Beta-phenyl-hydroxyl-amin itself and certain of its derivatives are unstable in solution and particularly in alkaline solution, and even in a dry state, and, without special treatment, are not available for use as photographic developers. I
The present invention relates to photographic developers which are relatively stable in character. The new photographic developers contain or are made from salts of the hydroxyl-amins and more partic-' ularly salts with organic acids.
When a relatively concentrated solution of phenyl-hydroxyl-amin in water is treated with a solution of oxalic acid (say about 10%) there is produced almost instantly a. crystalline precipitate which is of stable character and which is also not very soluble in water. Under proper conditions a relatively pure precipitate can be obtained merely by filtering and washing. The resulting product I consider to be the oxalate (i. e., a salt of an organic acid) of the phenyl-hydroxyl-amin. It can be further purified and is stable in the air and can be kept for long periods of time.
Instead of combining the phenyl-hydroxylamin with oxalic acid. it can be combined with other organic acids such as citric, formic lactic, pyrogallic, tannic, etc, or in general Serial No. 491,296.
with such acids which have no detrimental action when combined with the phenyl-hydroxyl-amin, that is, no action detrimental for use as photographic developers. The acids employed should not of course be of such a character that the action of the developer will be destroyed or detrimentally influenced to an objectionable extent; acids enhancing the developing qualities are of particular value.
The new photographic developers contain the hydroxyl-amin substancewith other suitable ingredients, including, if desired, also such as will tend to prevent or retard any too rapid'or objectionable oxidation of the hydroxyl-amin substance itself, particularly in the alkaline solution.
I have found the following compositions well adapted for use for photographic developing purposes:
For a paper developer dissolve in 100 ounces of Water- Sodium sulfite (dry) 5- ounces Hydroquinone y 1 ounce. Phenyl-hydroxyl-amin oxalate (as above described) p ounce. Sodium carbonate (anhydrous) 10 ounces. Potassium bromide (crystalline 6 grains.
Water 10 ounces. Sodium sulfite (dry) 20 grains. Hydroquinone 40 grains.
Phenyl-hydroxyl-amin oxalate- 20 grainso (as above described) Sodium carbonate (anhydrous) 600 grains. Potasiurn bromide (crystalline) 4 graiirs In using this developer it can be diluted with water to the desired extent, and may then be used for developing films in much the usual manner, but with added advantage to the developing process and to the result produced.
Modifications of these formulae as to quantity and nature of the added ingredicuts to meet various conditions for which the developer is to be used are to be considered as Within the scope of the invention. Such additions may be for modifying the tone or increasing or retarding the action of the developer, etc.
Instead of the salts of phenyl-hydroxylamin itself with organic acids, other suitable compounds or salts of its homolo-gues or of other aromatic hydroxyl-amins, such as naphtyl-hydroxyl-amin, etc., and their derivatives may be employed.
When using solid salts of the character described which are relatively stable, these salts can be kept for considerable periods of time and used in a dry state when desired, or they can be combined with other dry ingredients of the developer and the composite developer then added to water, or to other solution for use. The developer may thus be put up in tablet form, etc., either pure or mixed.
From the above formulae it will be noted that the phenyl-hydroxyl-amin oxalate is compounded With sodium sulfite and sodium carbonate as well as with other developer ingredients, for example, hydroquinone and potassium bromide. The sodium sulfite contributes to the developer composition and also has a protective influence upon the alkaline solution of the hydroxylamin substances, Other substances having similar action may be employed.
Variations and modifications can be made in the photographic developer without departing from the invention. For example, other phenyl-hydroxyl-amin compounds and derivatives may be similarly used as well as other photographic developer ingredients such as would be considered by those skilled in the art of value or as equivalents of those mentioned.
I do not claim herein the new salts of aromatic hydroxyl-amins with organic acids as these form the subject of my prior application, Serial No. 267,409, filed December 18, 1918, which matured into Patent No. 1,390,260, dated Sept. 6, 1921, of which, this application is a division.
I claim: h
1. A photographic developer containing an organic acid saltof an aromatic hydoxylamin together with other developer ingre' dients.
2. A photographic developer containing an organic acid salt of phenyl-hydroxylamin together with other developer ingredients.
3. A photographer developer containing an organic acid salt of an aromatic hydroxyl-amin together with sodium sulfite and other developer ingredients.
4. A photographic developer containing an organic acidg,.salt of phenyl-hydroxylamin together with sodium sulfite and other developer ingredients.
5. A photographic developer containing phenyl-hydroxyl-amin oxalate together with other developer ingredients.
6. A photographic developer comprising an alkaline solution containing an organic acid salt of an aromatic hydroxyl-amin, and sodium sulfite.
7. A photographic developer comprising an alkaline solution containing an organic acid salt of phenyl-hydroxyl-amin and sodium sulfite.
8. A photographic developer comprising an aqueous solution of phenyl-hydroxylamin oxalate, together with sodium sulfite and sodium carbonate.
9. A photographic developer containing phenyl-hydroxyl-amin oxalate together with sodium sulfite.
10. A photographic developer comprising a solution in water of phenyl-hydroxylamin oxalate sodium sulfite, sodium carbonate, and hydroquinone.
11. A photographic developer comprising a solution in water of phenyl-hydroxylamin, oxalate sodium sulfite, sodium carbonate, potassium bromide, and hydroquinone.
12. A photographic developer containing in a dry state a stable aromatic hydroxylamin compound.
13. A photographic developer containing in a dry state a stable aromatic hydroxyl- 2min compound together with sodium sul- 14. A photographic developer containing 'in a dry state a stable aromatic hydroxylamin compound together with sodium sulfite and hydro-quinone.
15. A photographic developer comprising a stable aqueous solution of an aromatic hydroxyl-amin compound together with sodium sulfite, hydro-quinone and sodium carbonate.
16. A photographic developer comprising a stable aqueous solution of an aromatic hydroxyl-amin compound together with a protective ingredient preventing objectionable too rapid oxidation of such compound.
17. The process of developing photograpic materials, which comprises treatinthe same with a'solution of an organic acid salt of an aromatic hydroxyl-amin containing sodium sulfite and alkali.
18. The process of developing photographic materials, which comprises treating the same with a solution of phenyl-hydroxyL amin oxalate containing sodium sulfite and sodium carbonate.
19.. The process of developing photo-=- graphic materials, which comprises treating the same w1th a stable solutlon of an aromatic hydroxyl-amin susbstanoe containing sodium sulfite, sodium carbonate and hydro- 5 quinone.
20. The process of developing photographic materials, which comprises treating same with a solution of phenyl-hydroxylamin oxalate containing also sodium sul- 10 fite hydroquinone and sodium carbonate.
21. The process of developing photographic materials, which comprises treating same with a solution of phenyl-hydroxl-amin oxalate containing also sodium sulfite, hydroquinone, sodium carbonate, and potassium bromide.
In testimony whereof I aflix my signature.
NATHAN SULZBERGER.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1516161A true US1516161A (en) | 1924-11-18 |
Family
ID=3407659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US1516161D Expired - Lifetime US1516161A (en) | Nathan sulzberger |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1516161A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1985004025A1 (en) * | 1984-03-02 | 1985-09-12 | Minnesota Mining And Manufacturing Company | Photographic tanning developer formulation |
-
0
- US US1516161D patent/US1516161A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1985004025A1 (en) * | 1984-03-02 | 1985-09-12 | Minnesota Mining And Manufacturing Company | Photographic tanning developer formulation |
| US4699868A (en) * | 1984-03-02 | 1987-10-13 | Minnesota Mining And Manufacturing Company | Photographic tanning developer formulation |
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