US3265502A - Photographic developing compositions - Google Patents
Photographic developing compositions Download PDFInfo
- Publication number
- US3265502A US3265502A US203750A US20375062A US3265502A US 3265502 A US3265502 A US 3265502A US 203750 A US203750 A US 203750A US 20375062 A US20375062 A US 20375062A US 3265502 A US3265502 A US 3265502A
- Authority
- US
- United States
- Prior art keywords
- group
- bath
- developing
- hydroquinone
- compound
- 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
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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
Definitions
- a further object of this invention is to provide developing compositions comprising hydroquinone and a p-phenylene diamine derivative as described hereinafter.
- Each of R and R represents a member selected from the group consisting of an alkyl radical such as an ethyl radical and a substituted alkyl radical such as a hydroxyethyl radical, and
- X represents an electro-negative group suchas an amino group, a monoalkylamino group, a dialkyl amino group, a sulfonamido group and an alkoxy group, and
- R represents a member selected from the group consisting of a hydrogen atom and an alkyl radical
- Each of R and R represents a member selected from the group consisting of a hydrogen atom and an alkyl radical
- n represents an integer from at least 2 and at most 3,
- X represents a member selected from the group consisting of a hydrogen atom, an alkyl radical and anelectronegative group such as an amino group, a monoalkylamino group, a dialkyl amino group, a sulfonamido group and an alkoxy group.
- N,N,N,N' tetramethyl p phenylene diamine dihydrochloride (2) N,N,N',N'-tetraethyl-p-phenylene diamine dihydrochloride (3) N,N-diethyl-N,N-dimethyl-p-phenylene diamine dihydrochloride (4) N,N diethyl N Z-hydroxyethyl N ethyl pphenylene diamine disulfate (5) N,N diethyl N 4 sulfobutyl N ethyl pphenylene diamine (b) Compounds according to general Formula II:
- Compound 11 is prepared by the alkylation of tetrahydroquinoline with butane sultone followed by coupling with the diazonium salt of 2,4-dichloroaniline and reduction of the azo dyestufl.
- Said compounds are weak developing agents if used in the absence of hydroquinone.
- a developing bath according to this invention may also contain ingredients such as buffer compositions which may comprise salts such as carbonates, borates, phosphates, bisulfites, metabisulfites, sulfites and acids such as boric acid and citric acid.
- the developing bath may further contain potassium bromide, water-softening agents such as polyphosphates or derivatives of ethylene diamine tetraacetic acid, antifogging agents and moistening agents, as well as other compounds known in the developing technique.
- the pH of the baths can vary within wide limits, preferably between 8 and 11, so that a quick and hard development or a slow and soft development can be obtained at will.
- the ratio of hydroquinone to a p-phenylene diamine derivative used in the present invention can be chosen in such a way that the bath composition is suited for the development of all kinds of materials including materials having silver chloride emulsion layers of low sensitivity as well as materials having highly sensitive silver brornoiodide emulsion layers.
- the ratio of hydroquinone to the p-phenylene diamine derivatives used in the present invention can vary within lwide limits.
- the amounts are, however, generally chosen in such a way that the hydroquinone strongly outweighs the said p-phenylene diamine derivatives.
- a strong superadditive effect is already obtained with a ratio of 50 mg. of a p-phenylene diamine derivative used in this invention to 5 g. of hydroquinone per litre. Larger amounts can also be used, although the superadditive effect which is obtained with concentrations of 1 to 2 g. of said p-phenylene diamine derivative and 5 to g. of hydroquinone per litre, is not much higher than With concentrations which are 10 times lower.
- the developing solutions according to this invention containing a combination of developing agents as described above, show with regard to the developing combination of hydroquinone and p-monomethylaminophenol hemisulfate the advantage that for a same developing activity a lower concentration of developing agents can be used.
- the developing agents used in the present invention show more particularly with regard to the developing combination of hydroquinone and l-phenyl-B-pyrazolidone the advantage of being stable to hydrolysis, even in strong alkaline medium.
- Example I Strips of a photographic material comprising a lightsensitive silver bromoiodide emulsion layer, coated onto a cellulose triacetate support, are exposed through a grey filter with a light-quantity (E) which corresponds to the shoulder part of the density/log E curve.
- E light-quantity
- Each of these exposed strips are developed at 20 C. in separate developing baths.
- One of them is developed in a bath A containing as developing agent only hydroquinone and having the following composition:
- the other strips are respectively developed in baths, having the same composition as bath A but containing moreover an equivalent amount of a developing agent as listed in Table 1 given hereinafter.
- the densities are determined respectively after a developing time of 1, 3, 5
- Example 2 Strips of a photographic material comprising a lightsensitive silver bromoiodide emulsion layer, coated on a cellulose triacetate support, are exposed through a grey filter with a light-quantity ('E) which corresponds to the shoulder part of the density/ log E curve.
- 'E light-quantity
- One of these film strips is developed in a bath B having the following composition:
- the other strips are respectively developed in baths having the same composition as bath B but moreover containing an equivalent amount of a developing agent as listed in Table 2 given hereinafter.
- the other strips are respectively developed in developing baths having the same composition as bath D, but containing moreover an equivalent amount of a developing agent as listed in Table 4 given hereinafter.
- Photographic developing solution comprising hydroquinone and a derivative of p-phenylene diamine having a pol-arographic half-wave potentialwhich is at least 40 mv. more negative than that of N,N-diethyl-p-phenylene diamine and corresponding to a general formula selected from the group consisting of:
- each of R R and R represents a lower alkyl radical
- Y represents a member selected from the group consisting of a hydrogen atom, a hydroxyl group, and a sulfonic acid group and salts thereof
- n represents an integer of at least 2 and at most 8 when Y represents a hydrogen atom or a hydroxyl group; and an integer of at least 3 and at most 8 when Y represents a sulfonic acid group
- each of R and R represents a member selected from the group consisting of an alkyl radical a lower and a hydroxy-substituted lower alkyl radical, and X represents an electro-negative group selected from the group consisting of an amino group, a monoalkylamino group, a dialkylamino group, a sulfonamido group and an alkoxy group;
- R is a lower alkyl radical
- R and R each represent a member selected from the group consisting of a hydrogen atom and a lower alkyl radical
- n an integer of at least 2 and at most 3
- X represents a member selected firom the group consisting of a hydrogen atom, a lower alkyl radical, an amino group, a monoalkylamino group, a dialkyl amino group, a sulfonam-ide group and an alkoxy (IV H3 H;
- X represents a member selected from the group consisting of a hydrogen atom, a lower alkyl radical, an amino group, a sulfonamido group and an alkoxy p;
- Photographic developing solution containing per liter from 5 g. to g. of hydroquinone and from 50 mg. to 2 g. of a p-phenylene diamine derivative having a polarographic half-wave potential which is at least 40 mv. more negative than that of N,N-diethyl-p-phenylene diamine and corresponding to a general formula selected from the group consisting of:
- each of R R and R represents a lower alkyl radical
- Y represents a member selected from the group consisting of a hydrogen atom a hydroxyl group, and a sulfonic acid group and salts thereof,
- n represents an integer of at least 2 and at most 8 when Y represents a hydrogen atom or a hydroxyl group; and an integer of at least 3 and at most 8 when Y represents a sulfonic acid group;
- each of R and R represents a member selected from the group consisting of a lower alkyl radical and a hydroxy substituted lower alkyl radical
- n represents an integer of at least 2 and at most 3
- X represents a member selected from the group consisting of a hydrogen atom, a lower alkyl radical, an amino group, a monalkylamino group, a dialkyl amino group, a sulfonamide group and an alkoxy group;
- each of R R and R represents a lower alkyl radical
- Y represents a member selected from the group consisting of a hydrogen atom, a hydroxyl group and a sulfonic acid group in free acid and salt form
- n represents an integer of at least 2 and at most 8 when Y represents a hydrogen atom or a hydroxyl group, but an integer of at least 3 and at most 8 when Y represents a sulfonic acid group;
- each of R and R represents a member selected from the group consisting of a lower alkyl radical and .a hydroxy-substituted lower alkyl radical
- X represents an electro-negative group selected from the group consisting of an amino group, a monoalkylamino group, a dialkylamino group, a sulfonwherein:
- amido group and X represents a member selected from the group conan alkoxy group; sisting of a hydrogen atom, a lower alkyl radical, an amino group, a sulfonamido group and an alkoxy (III) 1 5 group; RFN (V.) and the salts thereof.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE2040745 | 1961-06-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3265502A true US3265502A (en) | 1966-08-09 |
Family
ID=3864750
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US203750A Expired - Lifetime US3265502A (en) | 1961-06-21 | 1962-06-20 | Photographic developing compositions |
Country Status (4)
Country | Link |
---|---|
US (1) | US3265502A (no) |
BE (1) | BE605204A (no) |
DE (1) | DE1282454B (no) |
GB (1) | GB989383A (no) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3656950A (en) * | 1970-12-03 | 1972-04-18 | Eastman Kodak Co | Color photographic processes |
US3658525A (en) * | 1970-12-03 | 1972-04-25 | Eastman Kodak Co | Reversal color photographic processes |
US3723117A (en) * | 1969-10-27 | 1973-03-27 | Agfa Gevaert | Method for developing silver halide emulsions |
US3767403A (en) * | 1970-12-01 | 1973-10-23 | Agfa Gevaert Nv | Tetra-alkyl p-phenylene diamine with aromatic primary amino color developing agent |
US4004926A (en) * | 1974-04-02 | 1977-01-25 | Agfa-Gevaert N.V. | Formation of azine dyes |
US4514494A (en) * | 1982-11-12 | 1985-04-30 | Agfa-Gevaert N.V. | Photographic color material incorporating developing agents for color development |
US5492796A (en) * | 1993-10-28 | 1996-02-20 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material and processing method thereof |
US6265141B1 (en) * | 1993-07-24 | 2001-07-24 | Fuji Photo Film Co., Ltd. | Color developing agent, processing liquid composition and color image-forming method |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE969677C (de) * | 1952-04-25 | 1958-07-03 | Hauff G M B H | Verfahren zur Herstellung eines aktivierten photographischen Schwarzweissentwicklers |
US2848326A (en) * | 1955-09-26 | 1958-08-19 | Eastman Kodak Co | Method for preparing masked images |
-
0
- BE BE605204D patent/BE605204A/xx unknown
-
1962
- 1962-06-18 GB GB23349/62A patent/GB989383A/en not_active Expired
- 1962-06-20 US US203750A patent/US3265502A/en not_active Expired - Lifetime
- 1962-06-20 DE DEG35260A patent/DE1282454B/de active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE969677C (de) * | 1952-04-25 | 1958-07-03 | Hauff G M B H | Verfahren zur Herstellung eines aktivierten photographischen Schwarzweissentwicklers |
US2848326A (en) * | 1955-09-26 | 1958-08-19 | Eastman Kodak Co | Method for preparing masked images |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3723117A (en) * | 1969-10-27 | 1973-03-27 | Agfa Gevaert | Method for developing silver halide emulsions |
US3767403A (en) * | 1970-12-01 | 1973-10-23 | Agfa Gevaert Nv | Tetra-alkyl p-phenylene diamine with aromatic primary amino color developing agent |
US3656950A (en) * | 1970-12-03 | 1972-04-18 | Eastman Kodak Co | Color photographic processes |
US3658525A (en) * | 1970-12-03 | 1972-04-25 | Eastman Kodak Co | Reversal color photographic processes |
US4004926A (en) * | 1974-04-02 | 1977-01-25 | Agfa-Gevaert N.V. | Formation of azine dyes |
US4514494A (en) * | 1982-11-12 | 1985-04-30 | Agfa-Gevaert N.V. | Photographic color material incorporating developing agents for color development |
US6265141B1 (en) * | 1993-07-24 | 2001-07-24 | Fuji Photo Film Co., Ltd. | Color developing agent, processing liquid composition and color image-forming method |
US5492796A (en) * | 1993-10-28 | 1996-02-20 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material and processing method thereof |
Also Published As
Publication number | Publication date |
---|---|
GB989383A (en) | 1965-04-14 |
BE605204A (no) | |
DE1282454B (de) | 1968-11-07 |
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