US1937844A - Photographic developer and method of developing - Google Patents
Photographic developer and method of developing Download PDFInfo
- Publication number
- US1937844A US1937844A US524759A US52475931A US1937844A US 1937844 A US1937844 A US 1937844A US 524759 A US524759 A US 524759A US 52475931 A US52475931 A US 52475931A US 1937844 A US1937844 A US 1937844A
- Authority
- US
- United States
- Prior art keywords
- hydroxy
- developing
- phenyl
- morpholine
- 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
- 238000000034 method Methods 0.000 title description 7
- -1 silver halide Chemical class 0.000 description 15
- 239000000839 emulsion Substances 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 229910052709 silver Inorganic materials 0.000 description 7
- 239000004332 silver Substances 0.000 description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000012670 alkaline solution Substances 0.000 description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 235000014676 Phragmites communis Nutrition 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 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
- COHCRTRMRJCDKH-UHFFFAOYSA-N 1-phenylpiperidin-2-ol Chemical compound OC1CCCCN1C1=CC=CC=C1 COHCRTRMRJCDKH-UHFFFAOYSA-N 0.000 description 1
- LUMGYKRBEHCMRT-UHFFFAOYSA-N 1-phenylpyrrolidin-2-ol Chemical compound OC1CCCN1C1=CC=CC=C1 LUMGYKRBEHCMRT-UHFFFAOYSA-N 0.000 description 1
- HDGMAACKJSBLMW-UHFFFAOYSA-N 4-amino-2-methylphenol Chemical compound CC1=CC(N)=CC=C1O HDGMAACKJSBLMW-UHFFFAOYSA-N 0.000 description 1
- AKRDVABMCRJERJ-UHFFFAOYSA-N 4-phenylmorpholin-2-ol Chemical compound OC1CN(CCO1)C1=CC=CC=C1 AKRDVABMCRJERJ-UHFFFAOYSA-N 0.000 description 1
- VXQBJTIVNOMOKE-UHFFFAOYSA-N 4-phenylmorpholin-3-ol Chemical compound OC1COCCN1C1=CC=CC=C1 VXQBJTIVNOMOKE-UHFFFAOYSA-N 0.000 description 1
- FHQRDEDZJIFJAL-UHFFFAOYSA-N 4-phenylmorpholine Chemical compound C1COCCN1C1=CC=CC=C1 FHQRDEDZJIFJAL-UHFFFAOYSA-N 0.000 description 1
- CCLIIPCUCXRJEG-UHFFFAOYSA-N 4-phenylmorpholine-3,3-diol Chemical compound OC1(O)COCCN1C1=CC=CC=C1 CCLIIPCUCXRJEG-UHFFFAOYSA-N 0.000 description 1
- KFUHTPMPGRGNBS-UHFFFAOYSA-N 4-phenylthiomorpholin-3-ol Chemical compound OC1N(CCSC1)C1=CC=CC=C1 KFUHTPMPGRGNBS-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 230000033458 reproduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- This invention relates to the art of photography and particularly to the development of latent images in silver halide photographic emulsions.
- a developing solution is prepared containing as developer m-methyl p-hydroxy N-phenyl morpholine CHI-CH1 than the ones which are now in common use.
- the new developers which are employed in accordance with this invention are members of a class of substances having the general formula where the dotted line indicates the atoms required to complete the heterocyclic ring, R is an arcmatic nucleus, and X is a reducinggrouping such as .a hydroxyl or amino group.
- the preferred members of the class are compounds in which the heterocyclic ring contains an oxygen or sulphur atom and in which X is a hydroxyl group, such as the hydroxy-aryl morpholines.
- the following substances are typical members of the class described above: p-hydroxy N-phenyl morphollne, m-methyl p-hydroxy N-phenyl morpholine, m-methoxy p-hydroxy N- phenyl morpholine, m-hydroxy N-phenyl morpholine, o-hydroxy N-phenyl morpholine, hydroxy N-naphthyl morpholine, 'hydroxy N- biphe+ nyl morpholine, dihydroxy N-phenyl morpholine, amino hydroxy N-phenyl morpholine, ethylamino hydroxy N-phenyl morpholine, hydroxy N-phenyl thiomorpholine, hydroxy N-phenyl piperidine, p, p'-dihydroxy, N, Ndiphenyl piperazine, hydroxy 1.4 phenylene dimorpholine,.hydroxy N-phenyl pyrrole, hydroxy N-phenyl pyr
- CHI-CH CHI-CH
- the new developers of this invention are admirably adapted for tank development, because of their tendency to correct the effects of improper, exposure. They are particularly desirable for landscape or portrait work where the ability to reproduce detail is of greater importance than the production of the utmost degree of contrast. They may be kept in stock almost indefinitely, either dry or in the form of a solution, are far more stable than the majority ofthe developers now in common use, and do not deteriorate on'standing, even in moderately'strong sunlight.
- a photographic developer comprising a solution of a compound having the structural formula where the dotted line indicates the atoms required to complete the heterocyclic ring, R is an aromatic nucleus, and X is a hydroxyl or amino group.
- a photographic developer comprising a solution of a compound having the structural formula 0 1 ⁇ NR0H 6.
- a photographic developer comprising a solution of m-methyl p-hydroxy N-phenyl morpholine.
- a photographic developer comprising a dilute aqueous solution or a hydroxy N-aryl morhn pholine.
- a photographic developer comprising a dilute alkaline aqueous solution of a hydroxy N-aryl morpholine.
- a process of developing photographic images which comprises treating a silver halide photographic emulsion which has been exposed to the light with a compound having the structural formula where the dotted line indicates the atoms required to complete the heterocyclic ring, R is an 'where the dotted line indicates the atoms required to complete a six-membered, saturated, heterocyclic ring, and R is an aromatic nucleus.
- a process of developing photographic images which comprises immersing a silver halide photographic emulsion which has been exposed to the light in an aqueous solution comprising a hydroxy N-aryl morpholine.
- a process of developing photographic images which comprises immersing a silver halide photographic emulsion which has been exposed to the light in an aqueous solution comprising a hydroxy N-aryl morpholine in which the aryl group contains only one aromatic ring.
- Alprocess of developing photographic images which comprises immersing a silver halide photographic emulsion which has been exposed to the light in a dilute, aqueous, alkaline solution comprising a p-hydroxy N-aryl morpholine in which the aryl group contains only one aromatic ring.
- a process of developing photographic images which comprises immersing a silver halide photographic emulsion which has been exposed to the light in an aqueous, alkaline solution comprising m-methyl p-hydroxy N-phenyl morpho- MARION o. REED.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
Patented Dec. 5, 1933 PATENT OFFICE PHOTOGRAPHIC DEVELOPER METHOD OF DEVELOPING Marion 0. Reed, Charleston,
The B. F. Goodrich Company,
W. Va., assignor to New York, N. Y.,
a corporation of New Iork No Drawing. Application March 23, 1931 Serial No. 524,759
14 Claims.
This invention relates to the art of photography and particularly to the development of latent images in silver halide photographic emulsions.
It has been the general practice to develop silver halide photographic emulsions such as those on the familiar dry plates, photo graphic films, bromide and gas-light papers, etc., by immersing them in a mildly alkaline solution of an organic reducing agent such as hydroquinone, pyrogallol, monomethyl p-aminophenol, glycine, etc. The chief object of this invention, then, is to provide a new class of developing agents which exhibit certain distinct advantages over the previously known developers. Another object is to provide a class of developers which are far less expensive somewhat greater proopers and the superior resultsattained by their 7 use.
As a specific example of one embodiment of this invention, a developing solution is prepared containing as developer m-methyl p-hydroxy N-phenyl morpholine CHI-CH1 than the ones which are now in common use.
Other objects will be evident from the following description of the invention.
The new developers which are employed in accordance with this invention are members of a class of substances having the general formula where the dotted line indicates the atoms required to complete the heterocyclic ring, R is an arcmatic nucleus, and X is a reducinggrouping such as .a hydroxyl or amino group. The preferred members of the class are compounds in which the heterocyclic ring contains an oxygen or sulphur atom and in which X is a hydroxyl group, such as the hydroxy-aryl morpholines. The following substances, for example, are typical members of the class described above: p-hydroxy N-phenyl morphollne, m-methyl p-hydroxy N-phenyl morpholine, m-methoxy p-hydroxy N- phenyl morpholine, m-hydroxy N-phenyl morpholine, o-hydroxy N-phenyl morpholine, hydroxy N-naphthyl morpholine, 'hydroxy N- biphe+ nyl morpholine, dihydroxy N-phenyl morpholine, amino hydroxy N-phenyl morpholine, ethylamino hydroxy N-phenyl morpholine, hydroxy N-phenyl thiomorpholine, hydroxy N-phenyl piperidine, p, p'-dihydroxy, N, Ndiphenyl piperazine, hydroxy 1.4 phenylene dimorpholine,.hydroxy N-phenyl pyrrole, hydroxy N-phenyl tetra-hydro pyrrole, hydrox N-phenyl hydroxyquinoline, p-amino N- phenyl morpholine, diamino N-phenyl morpholine, monomethyl dlamino N-phenyl morpholine, etc.
The new developers of the class described above may be used for the development of photographic exposure to light are CHI-CH:
according to the following formula:
. Parts Sodium sulphite 3 Developer '7 Sodium carbonate 6 -Water 1000 Plates or films which have been given a normal developed by immersion in the solution for from 15 to 25 minutes at a temperature of about 18 C. (65 F.).' They are then washed, fixed in a solution of sodium hyposulphite and washed thoroughly, in the usual manner. The photographic reproductions obtained by this process are soft and pleasing, well brought out by the action of the developer, while at the same time the contrast is good and sharp and the whites are clear. The new develexposure, good results being obtained even with emulsions which are somewhat under or over-i exposed.
The new developers of this invention are admirably adapted for tank development, because of their tendency to correct the effects of improper, exposure. They are particularly desirable for landscape or portrait work where the ability to reproduce detail is of greater importance than the production of the utmost degree of contrast. They may be kept in stock almost indefinitely, either dry or in the form of a solution, are far more stable than the majority ofthe developers now in common use, and do not deteriorate on'standing, even in moderately'strong sunlight.
Although a specific embodiment of the invention has been described ticularity, it is to be understood that this invention is not limited thereby, but that it 18 ll"- the details being oper allows an unusual latitude in the degree of for they with considerable porceptible of numerous variations within the scope of the appended claims, as will be obvious to those skilled in the art. In particular, the new developers of this-invention may be used in conjunction with other known developers, or with other salts, acids or alkalies to modify the properties of the developing solution or of the photographic images obtained thereby. Such modifications are well known expedients and need not be described here.
This invention is a continuation in part of my copending application Serial No. 442,043, filed April 5, 1930.
I claim:
1. A photographic developer comprising a solution of a compound having the structural formula where the dotted line indicates the atoms required to complete the heterocyclic ring, R is an aromatic nucleus, and X is a hydroxyl or amino group.
2. A photographic developer comprising a solution of a compound having the structural formula 0 1 \NR0H 6. A photographic developer comprising a solution of m-methyl p-hydroxy N-phenyl morpholine.
7. A photographic developer comprising a dilute aqueous solution or a hydroxy N-aryl morhn pholine.
I 8. A photographic developer comprising a dilute alkaline aqueous solution of a hydroxy N-aryl morpholine.
9. A process of developing photographic images which comprises treating a silver halide photographic emulsion which has been exposed to the light with a compound having the structural formula where the dotted line indicates the atoms required to complete the heterocyclic ring, R is an 'where the dotted line indicates the atoms required to complete a six-membered, saturated, heterocyclic ring, and R is an aromatic nucleus.
11. A process of developing photographic images which comprises immersing a silver halide photographic emulsion which has been exposed to the light in an aqueous solution comprising a hydroxy N-aryl morpholine.
' 12. A process of developing photographic images which comprises immersing a silver halide photographic emulsion which has been exposed to the light in an aqueous solution comprising a hydroxy N-aryl morpholine in which the aryl group contains only one aromatic ring.
13. Alprocess of developing photographic images which comprises immersing a silver halide photographic emulsion which has been exposed to the light in a dilute, aqueous, alkaline solution comprising a p-hydroxy N-aryl morpholine in which the aryl group contains only one aromatic ring.
14. A process of developing photographic images which comprises immersing a silver halide photographic emulsion which has been exposed to the light in an aqueous, alkaline solution comprising m-methyl p-hydroxy N-phenyl morpho- MARION o. REED.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US524759A US1937844A (en) | 1931-03-23 | 1931-03-23 | Photographic developer and method of developing |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US524759A US1937844A (en) | 1931-03-23 | 1931-03-23 | Photographic developer and method of developing |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1937844A true US1937844A (en) | 1933-12-05 |
Family
ID=24090567
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US524759A Expired - Lifetime US1937844A (en) | 1931-03-23 | 1931-03-23 | Photographic developer and method of developing |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1937844A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE743536C (en) * | 1937-10-21 | 1944-01-06 | Ig Farbenindustrie Ag | Process for the color development of photographic silver halide emulsions |
| US2843481A (en) * | 1954-07-19 | 1958-07-15 | Polaroid Corp | Photographic processes |
| US2981623A (en) * | 1954-03-15 | 1961-04-25 | Agfa Ag | Photographic developers |
| US3134673A (en) * | 1960-02-19 | 1964-05-26 | Ilford Ltd | Photographic developers |
| US3392170A (en) * | 1965-08-27 | 1968-07-09 | Monsanto Co | 4-[p-(substituted amino) phenyl] morpholines |
| US4851325A (en) * | 1986-07-12 | 1989-07-25 | Fuji Photo Film Co., Inc. | Process for producing silver halide color photographic materials comprising a heterocyclic developing agent |
-
1931
- 1931-03-23 US US524759A patent/US1937844A/en not_active Expired - Lifetime
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE743536C (en) * | 1937-10-21 | 1944-01-06 | Ig Farbenindustrie Ag | Process for the color development of photographic silver halide emulsions |
| US2981623A (en) * | 1954-03-15 | 1961-04-25 | Agfa Ag | Photographic developers |
| US2843481A (en) * | 1954-07-19 | 1958-07-15 | Polaroid Corp | Photographic processes |
| US3134673A (en) * | 1960-02-19 | 1964-05-26 | Ilford Ltd | Photographic developers |
| US3392170A (en) * | 1965-08-27 | 1968-07-09 | Monsanto Co | 4-[p-(substituted amino) phenyl] morpholines |
| US4851325A (en) * | 1986-07-12 | 1989-07-25 | Fuji Photo Film Co., Inc. | Process for producing silver halide color photographic materials comprising a heterocyclic developing agent |
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