US1853455A - Photographic developer - Google Patents
Photographic developer Download PDFInfo
- Publication number
- US1853455A US1853455A US468451A US46845130A US1853455A US 1853455 A US1853455 A US 1853455A US 468451 A US468451 A US 468451A US 46845130 A US46845130 A US 46845130A US 1853455 A US1853455 A US 1853455A
- Authority
- US
- United States
- Prior art keywords
- grams
- hydroxyethyl
- developer
- meaning
- acyl
- 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
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical class C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 15
- 125000002252 acyl group Chemical group 0.000 description 13
- 239000000463 material Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 229960003742 phenol Drugs 0.000 description 9
- 239000012670 alkaline solution Substances 0.000 description 8
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 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 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 235000010265 sodium sulphite Nutrition 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- -1 silver halide Chemical class 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- YJLUBHOZZTYQIP-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=N2 YJLUBHOZZTYQIP-UHFFFAOYSA-N 0.000 description 1
- XPRLHMHGYOTAPD-UHFFFAOYSA-N 2-amino-4-(2-hydroxyethylamino)phenol Chemical compound NC1=CC(NCCO)=CC=C1O XPRLHMHGYOTAPD-UHFFFAOYSA-N 0.000 description 1
- PRVKSXDMKVXNIR-UHFFFAOYSA-N 4-amino-2-(2-hydroxyethylamino)phenol Chemical compound NC1=CC=C(O)C(NCCO)=C1 PRVKSXDMKVXNIR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006467 substitution reaction 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
- 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
- G03C5/30—Developers
- G03C5/3021—Developers with oxydisable hydroxyl or amine groups linked to an aromatic ring
Definitions
- Our present invention relates to a process of developing photographic materials and new photographic developers.
- the compounds in question correspond to the general formula a v m, as, 3 3 meaning hydrogen, acyl, hydroxyethyl, at least one of these substituents being the hydroxyethyl, residue and at least one meaning hydrogen.
- the sai compounds are very stable in solid and in dissolved condition are markably soluble and have the particular prop erty of developing the latent photographle image in a silver halide emulsion without formation of fog, even in solutions free from potassium bromide.
- Example 1 5 grams of the sulfate of 4-hydroxyethylamino-2- acetamino-I-h droxybenzene, 45 grams of crysta ized sodium suliite, and 1 grams of potassium carbonate are dissolved in grams of water.
- the developer has properties similar to those of the developer made from -hydroxyethylamino-l-hydroxybenzene.
- the developer is of a similar activity but in a steeper gradation, than that of the developer made in accordance w1th our U. S. Patent 1,758,762.
- This developer is similar in action to the 2.4-diamino-l-hydroxybenzene.
- Example 4 85 grams of the sulfate of 2-hydroxyethylamino-4- amino-l-hydroxybenzene, 10 grams or crystallized sodium sulflte, and 55 0. 2 grams of potassium bromide are dissolved in 200 grams or water.
- E'aample 5 1. 5 grams of the sulfate of 4-di-[hydroxyethyl1-amino- 2-amino-1-h droxybenzene 10 grams 0! or s ilized sodium sulflte, and
- This developer is similar in action to that made from 2.4-diamino-1-hydroxybenzene.
- Example 6 1 gram of the sulfate 0! 2-di-[hydroxyethyl]-amino- 4-amiuo-1-hydroxybenzene and 20 grams of crystallized sodiumsulflte are dissolved in 200 grams of water.
- the developer is similar in action to a developer contalnmg 4-am1no-1-hydroxybenzene 1n the usual d1lut1on.
- Example '7 1. 5 grams oi. the sulfate of 2-di-[hydroxyethyl1-aminoi-amino-l-h droxybenzene and grams of cry llized sodium suliite, and
- w, w, y, 3 meaning H, acyl, hydroxyethyl at least one of these substituents being hydroxyethyl and at least one meaning hydrogen.
- a photographic developer containing together with other developer ingredients a compound of the general formula:
- a photographic developer containing together with other developer ingredients a compound of the general formula:
- H-NCH:CH:OH a meaning H, acyl, hydroxyethyl.
- a photographic developer comprising an alkaline solution containing a compound of the general formula:
- N 1 2 II N w, w, y, y' meaning H, acyl, hydroxyethyl at least one of these substituents being hydroxyethyl and at least one meaning hydrogen.
- a photographic developer comprising an alkaline solution containing a compound of the general formula: on
- IINCH:CH:0H a and 3 meaning H, acyl, hydroxyethyl.
- a photographic developer comprising an alkaline solution containing a compound of the general formula:
- H-NCH:CH1OH a meaning H, acyl, hydroxyethyl.
- a photographic developer comprising 1 an alkaline solution containing 2-acetylamino4-hydroxyethylamino 1 hydroxybenzene.
- N I I I I I m, m, y, y meaning H, acyl, hydroxyethyl at least one of these substituents being hydroxyethyl and'at least one meaning hydrogen.
- w and y meaning H, acyl, hydroxyethyl.
- HNOH:GH:0H w and y meaning H, acyl, hydroxyethyl.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Apr. 12, 1932 UNITED STATES PATENT OFFICE GUSTAV BEDDELIEN' AND WERNER MULLER, OF LEIPZIG, GERMANY, ASSIGNOBS 'IO .LGFL .L'N'BCO OOBPOBA'IION, OI BINGHAMTON, NEW YORK, A CORPORATION O! m YORK Io Drawing. Application filed July 16, 1980, Serial No. 468,451, and in Germany August 19, 1989.
Our present invention relates to a process of developing photographic materials and new photographic developers.
It is based on the observation that with the 6 exception of the compounds which are twice h droxyethylated at each nitrogen atom, the N hydroxyethyl derivatives of 2.4-diamino-1- hydroxybenzene or of N-mono-acyl-2A-diamino-l-hydroxybenzene or of the nucleal 1 substitution products of these compounds are well suited as photographic developers in so far as they contain no nitro groups.
The compounds in question correspond to the general formula a v m, as, 3 3 meaning hydrogen, acyl, hydroxyethyl, at least one of these substituents being the hydroxyethyl, residue and at least one meaning hydrogen.
The sai compounds are very stable in solid and in dissolved condition are markably soluble and have the particular prop erty of developing the latent photographle image in a silver halide emulsion without formation of fog, even in solutions free from potassium bromide.
The following examples illustrate suitable compositions for photographic developers in accordance with our invention:
Example 1 6. 5 grams of the sulfate of 4-hydroxyethylamino-2- acetamino-I-h droxybenzene, 45 grams of crysta ized sodium suliite, and 1 grams of potassium carbonate are dissolved in grams of water. The developer has properties similar to those of the developer made from -hydroxyethylamino-l-hydroxybenzene.
Example 2 gram of the hydrochloride of 2-hydroxyethylamino- 4-acetamiuo-1-hydroxybenzene,
grams of crystallized sodium sulflte. and
grams of potassium carbonate are dissolved in grams of water.
The developer is of a similar activity but in a steeper gradation, than that of the developer made in accordance w1th our U. S. Patent 1,758,762.
Example 3 5 grams 0! the sulfate of 4-hydroxyethylamino2- amino-l-hydroxybenzene,
45 grams of crystallized sodium sulflte, and
0, 1 gram of potassium bromide are dissolved in 1000 grams of water.
This developer is similar in action to the 2.4-diamino-l-hydroxybenzene.
Example 4 1. 85 grams of the sulfate of 2-hydroxyethylamino-4- amino-l-hydroxybenzene, 10 grams or crystallized sodium sulflte, and 55 0. 2 grams of potassium bromide are dissolved in 200 grams or water.
E'aample 5 1. 5 grams of the sulfate of 4-di-[hydroxyethyl1-amino- 2-amino-1-h droxybenzene 10 grams 0! or s ilized sodium sulflte, and
0, 4 gram oi po ssium bromide are dissolved in 200 grams of water.
This developer is similar in action to that made from 2.4-diamino-1-hydroxybenzene.
Example 6 1 gram of the sulfate 0! 2-di-[hydroxyethyl]-amino- 4-amiuo-1-hydroxybenzene and 20 grams of crystallized sodiumsulflte are dissolved in 200 grams of water.
The developer is similar in action to a developer contalnmg 4-am1no-1-hydroxybenzene 1n the usual d1lut1on.
Example '7 1. 5 grams oi. the sulfate of 2-di-[hydroxyethyl1-aminoi-amino-l-h droxybenzene and grams of cry llized sodium suliite, and
gram otfpotassium bromide are dissolved in grams 0 water.
w, w, y, 3 meaning H, acyl, hydroxyethyl at least one of these substituents being hydroxyethyl and at least one meaning hydrogen.
2. A photographic developer containing together with other developer ingredients a compound of the general formula:
H-NOH:CH:OH a: and y meaning H, acyl, hydroxyethyl.
3. A photographic developer containing together with other developer ingredients a compound of the general formula:
H-NCH:CH:OH a: meaning H, acyl, hydroxyethyl.
4. A photographic developer containing together with' other developer ingredients 2-acetylamino 4 hydroxy-ethylamino 1 hydroxybenzene. V
5. A photographic developer comprising an alkaline solution containing a compound of the general formula:
N 1 2 II N w, w, y, y' meaning H, acyl, hydroxyethyl at least one of these substituents being hydroxyethyl and at least one meaning hydrogen.
6. A photographic developer comprising an alkaline solution containing a compound of the general formula: on
IINCH:CH:0H a: and 3 meaning H, acyl, hydroxyethyl.
7 A photographic developer comprising an alkaline solution containing a compound of the general formula:
H-NCH:CH1OH a; meaning H, acyl, hydroxyethyl.
8. A photographic developer comprising 1 an alkaline solution containing 2-acetylamino4-hydroxyethylamino 1 hydroxybenzene.
9. The process of developing photographic materials which comprises treating the same with a solution containing a compound of the general formula:
N I I I I m, m, y, y meaning H, acyl, hydroxyethyl at least one of these substituents being hydroxyethyl and'at least one meaning hydrogen.
10. The process of developing photographic materials which comprises treating the same with a solution containing a compound of the general formula:
w and y meaning H, acyl, hydroxyethyl.
11. The process of developing photographic materials which comprises treating the same with a solution containing a compound of the general formula:
OH x
- H- OH|CH|OH w meaning H, acyl, hydroxyethyl.
12. The process of developing photographic materials which comprises treating the same with a solution containing 2-acetylamino-4;-hydroxyethylamino- 1 hydroxybenzene.
13. The process of developing photographic materials which comprises treating the same with an alkaline solution containing sodium sulfite and a compound of the general formula:
f 1 N 0 2 5 a w, 41 ;,y, 3 meaning H, acyl, hydroxyethyl at least one of these substituents being hydroxyethyl and at least one meaning hydrogen.
14. The process of developing photographic materials which comprises treating the same with an alkaline solution containing sodium sulfite and a compound of the general formula:
HNOH:GH:0H w and y meaning H, acyl, hydroxyethyl.
15. The process of developing photographic materials which comprises treating the same with an alkaline solution containing sodium sulfite and a compound of the general formula:
H- CH:0H:OH :1: meaning H, acyl, hydroxyethyl.
16. The process of developing photographic materials which compriscs treating the same with an alkaline solution containing sodium sulfite and 2-acetylamino-4c-hydroxyethylamino-l-hydroxybenzenc.
In testimony whereof, we afiix our signatures.
GUSTAV REDDELIEN. WERNER MULLER.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI39068D DE507022C (en) | 1926-11-19 | 1929-08-19 | Photographic developer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1853455A true US1853455A (en) | 1932-04-12 |
Family
ID=7189963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US468451A Expired - Lifetime US1853455A (en) | 1929-08-19 | 1930-07-16 | Photographic developer |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1853455A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3184387A (en) * | 1955-11-25 | 1965-05-18 | Oreal | Process for dyeing hair with substituted 2, 4-diaminophenols |
| US3291609A (en) * | 1964-06-05 | 1966-12-13 | Eastman Kodak Co | Developer incorporated photographic materials |
| US4329504A (en) * | 1976-08-20 | 1982-05-11 | Andree Bugaut | Metaphenylenediamines |
| US5145483A (en) * | 1988-10-28 | 1992-09-08 | L'oreal | Substituted ortho-aminophenols, process for preparing them and their use for the oxidatin dyeing of keratinous fibres |
-
1930
- 1930-07-16 US US468451A patent/US1853455A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3184387A (en) * | 1955-11-25 | 1965-05-18 | Oreal | Process for dyeing hair with substituted 2, 4-diaminophenols |
| US3291609A (en) * | 1964-06-05 | 1966-12-13 | Eastman Kodak Co | Developer incorporated photographic materials |
| US4329504A (en) * | 1976-08-20 | 1982-05-11 | Andree Bugaut | Metaphenylenediamines |
| US5145483A (en) * | 1988-10-28 | 1992-09-08 | L'oreal | Substituted ortho-aminophenols, process for preparing them and their use for the oxidatin dyeing of keratinous fibres |
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