US2163166A - Photographic developer - Google Patents

Photographic developer Download PDF

Info

Publication number
US2163166A
US2163166A US14372437A US2163166A US 2163166 A US2163166 A US 2163166A US 14372437 A US14372437 A US 14372437A US 2163166 A US2163166 A US 2163166A
Authority
US
Grant status
Grant
Patent type
Prior art keywords
mol
phenylenediamine
photographic developer
following formula
developers
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
Application number
Inventor
Wilmanns Gustav
Schneider Wilhelm
Wendt Bruno
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Agfa Ansco Corp
Original Assignee
Agfa Ansco Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Grant date

Links

Images

Classifications

    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/407Development processes or agents therefor
    • G03C7/413Developers
    • G03C7/4136Developers p-Phenylenediamine or derivatives thereof

Description

Patent ed June 193$ "UNITED s'r res PATENT. OFFICE 2,188,166 I PHOTOGRAPHIODEVELOPER v, Gustav Wilmanns, Woll'en, Bitterfeld, and Wilhelm Schneider and Bruno Wendt, Dessau, Anhalt, Germany, assignors, by mesne assignments, to Agfa Ansco Corporation, Bingham ton, N. Y., a. corporation of Delaware 1 I No Drawing. Application May 20,1937. Serial No; 143,724. In Germany May. 26, 1936 5 Claims. (Cl. 95'-88) Our present invention relates to photographic developers and more particularly to developers for development in colors.

One of-its objects is to provide new photographic developers of the para-phenylenediamine series. Further objects will be seen-from the detailed specification following hereafter.

Para-phenylenediamine is a known developer for silver halide emulsions. It is also known that wthe substitution products of developers of this class form, with suitable dyestuif "components, color pictures in the development. Substances suitable are described in UJS. Patent, 1 ,'102,028, dated June 30, 1914. Hitherto only'thederivatives of para-phenylenediamine whi'cii'are alkylated at the nitrogen atom have been used as color developers. All these bodies and especially the most suitable of them are, however, of only limited solubility in water or in a sodium carbonate solution. This fact is a drawback in that the developer is removed only withd'ifliculty by washing after the development, so that in sub- "sequent ly bleaching the silver picture with an oxidizing agent such as potassiumferricyanide undesired color is apt to be developed, particularly when suitable components are present;

Moreover, these substances are freely absorbed by the skin and give rise to malignant eczema and like troubles. All these disadvantages would be considerably ameliorated if the solubility of the compounds could be increased. It has been found that the introduction of 'carboxylic groups or sulfonic groups for increasing'the solubility is not satisfactory in this caseifl'the group enters the nucleus of the para-phenylenediamine, because then. the developing power is at the least strongly diminished.

This invention is based on the observation that valuable developing agents, particularly suitable for development in colors, may be obtained by introducing a sulfonlc or carboxylic group into a positive radical 'attachedto the nitrogen, so as to produce for example, paraamino-N-methyl-aniline-omega-sulfonic a c i d, para-amino-N-ethylaniline-omega-sulfonic acid. 4-amino-N-benzyl-aniline-4'-sulfonic acid, and so on. A formula for the developers of this invention is the following:

R Y R =alkylene arylene 1 ii=coonfsoan the para-phenylenediamine is unsubstituted or contains a further substituent in the free orthoor meta-position, a radical which contains several oxy-groups. It has already been proposed in U. S. Patent 2,108,243 dated February 15, 1938 to introduce hydroxyethyl-groups in the paraphenylenediamine. It has been shown, however,

that the solubility is not-sumcient to render the base easily soluble in water. The solubility is attained, however, if the paraphenylenediamine is caused to react with ethylene-oxide, for instance with 3 --to 5mol-ethylene-oxide. This ex- R X R=any positive groups, for instance hydrogen, alkyl aryl or hydroxyalkyl Nv X=[CH.OH1.O],.-CHMJHLOH n=a whole number These developers are well suited for black and white and also for color development, and their superior solubility and physiological harmlessness distinguish them from known phenylene= diamines. f

The two groups of' developers may be. combined in accordance with the following formula:

The following examples illustrate the invention: (1) 1 mol methylphenylamino-benzyl-2-propicnic acid is coupled with 1 mol of diazotized sulfanilic acid in the usual manner. The dye is precipitated and is filtered off and split by reducing with tin and hydrochloric acid. The tin is precipitated from the solution of the double-salt by means of sulfuretted hydrogen and the resulting developing agent is obtained by evaporating (2)1 mol"'of p-sulfobenzylaniiine is. coupled with l'molof diazotized sulfa'nilic acid, the dye is isolated and split in the same manner as disclosed in Example 1 with tin and hydrochloric acid. The hydrochloride of p-sulfobenzylamino-4-aniline is obtained from the tin double-salt and corresponds to the following formula:

W t rm Nm (3) 1 mol of di-(p -sulfobenzyD-aniline is coupled with 1 mol of diazotized sulfanilic acid and further treated in a manner analogous to that of Example 1. Di'-(p-su1fobenzyl)-aminoanilinehydrochloride which has the following formula:

(5) 1 mol of a condensation product obtained from 1 mol nitromethyl-m-toluidine and 2 mols ethyleneoxide yields after reduction with tin and hydrochloric acid. a product of the following formula:

CHr-N-JJHpOHnOJIHaCHLOH NHLHCI (6) 1 mol of a condensation product produced by the known method from 1 mol of ethylaniline and 2 mols of ethyleneoxide yields if treated according to the method of Example 1 a developer of the following formula:

NHI-HCI (7) 1 mol of the condensation product from 1 mol monoethyl-m-toluidine and 2 mols ethyleneoxide is treated in the same manner as described in Example 1. A compound of the following formula is obtained:

4 'OsHr-N-CHaCHaQCHaOHaOH I Name! What we claim is: g 1. A photographic developer containing a p-phenylenediamine having attached to one of the nitrogen atoms the radicle (CH2.CH2.O) a.CH:.CHs.OH,

wherein n is a whole number.

2. A photographic developer containing a p-phenylenediamine having attached to one of the nitrogen atoms the radicle (CHz.CH:.0) .CH:.CH:.OH,

wherein n is a whole number and a member selected from the group consisting of hydrogen.

alkyl, aryl and aralkyl.

3. A photographic developer containing a p-phenylenediamine corresponding with the following formula cmt-N-cmcmocm.0n,.o .cm.cm.on

NHI-HCI 4. A photographic developer containing a p-phenyienediamine corresponding with the following formula CHEN-Clix.0H|.0.CH1.CH1.0H

NHsHCl 5. A photographic developer containing a p-phenylenediamine corresponding with the following formula NHaHCl GUSTAV WILMANNS.

US2163166A 1936-05-27 1937-05-20 Photographic developer Expired - Lifetime US2163166A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DE1936I0055101 DE767652C (en) 1936-05-27 1936-05-27 Method for color development of silver halide emulsions
GB1596636A GB481275A (en) 1936-05-27 1936-06-08 Improvements relating to photographic developers

Publications (1)

Publication Number Publication Date
US2163166A true US2163166A (en) 1939-06-20

Family

ID=25981935

Family Applications (1)

Application Number Title Priority Date Filing Date
US2163166A Expired - Lifetime US2163166A (en) 1936-05-27 1937-05-20 Photographic developer

Country Status (4)

Country Link
US (1) US2163166A (en)
DE (1) DE767652C (en)
FR (1) FR822269A (en)
GB (1) GB481275A (en)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2449919A (en) * 1947-07-05 1948-09-21 Eastman Kodak Co 3-methylsulfonamido-4-amino dimethyl aniline photographic developer
US2486440A (en) * 1946-01-10 1949-11-01 Gen Aniline & Film Corp Production of phenazonium dyestuff images
US2575027A (en) * 1949-10-29 1951-11-13 Gen Aniline & Film Corp N-substituted 4, 6-diamino metanilic acids
US2603659A (en) * 1950-06-16 1952-07-15 Du Pont Photographic developers
US2603656A (en) * 1951-02-27 1952-07-15 Du Pont Photographic developing agents
US2604399A (en) * 1949-07-07 1952-07-22 Eastman Kodak Co Photographic developers comprising bis-(di-hydroxyalkyl aminomethyl)-hydroquinones
US2611785A (en) * 1952-09-23 N-substituted x
US2695234A (en) * 1951-01-26 1954-11-23 Gevaert Photo Prod Nv Photographic development
US2716132A (en) * 1952-10-22 1955-08-23 Du Pont N-substituted amino anilines
US3113124A (en) * 1959-11-27 1963-12-03 Pennsalt Chemicals Corp Novel antiozonants for elastomers
US3181942A (en) * 1961-11-15 1965-05-04 Pennsalt Chemicals Corp Method of controlling plant growth
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
US3661587A (en) * 1968-04-01 1972-05-09 Itek Corp Photographic media
US4066457A (en) * 1974-12-10 1978-01-03 Gaf Corporation Color developer for diffusion transfer
US4066456A (en) * 1974-12-10 1978-01-03 Gaf Corporation Incorporated carboxy substituted p-phenylenediamine color developer
US4113491A (en) * 1975-02-10 1978-09-12 Konishiroku Photo Industry Co., Ltd. Color photographic developing composition

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102755C (en) *
DE253335C (en) * 1912-02-06

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2611785A (en) * 1952-09-23 N-substituted x
US2486440A (en) * 1946-01-10 1949-11-01 Gen Aniline & Film Corp Production of phenazonium dyestuff images
US2449919A (en) * 1947-07-05 1948-09-21 Eastman Kodak Co 3-methylsulfonamido-4-amino dimethyl aniline photographic developer
US2604399A (en) * 1949-07-07 1952-07-22 Eastman Kodak Co Photographic developers comprising bis-(di-hydroxyalkyl aminomethyl)-hydroquinones
US2575027A (en) * 1949-10-29 1951-11-13 Gen Aniline & Film Corp N-substituted 4, 6-diamino metanilic acids
US2603659A (en) * 1950-06-16 1952-07-15 Du Pont Photographic developers
US2695234A (en) * 1951-01-26 1954-11-23 Gevaert Photo Prod Nv Photographic development
US2603656A (en) * 1951-02-27 1952-07-15 Du Pont Photographic developing agents
US2716132A (en) * 1952-10-22 1955-08-23 Du Pont N-substituted amino anilines
US3113124A (en) * 1959-11-27 1963-12-03 Pennsalt Chemicals Corp Novel antiozonants for elastomers
US3181942A (en) * 1961-11-15 1965-05-04 Pennsalt Chemicals Corp Method of controlling plant growth
US3661587A (en) * 1968-04-01 1972-05-09 Itek Corp Photographic media
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
US4066457A (en) * 1974-12-10 1978-01-03 Gaf Corporation Color developer for diffusion transfer
US4066456A (en) * 1974-12-10 1978-01-03 Gaf Corporation Incorporated carboxy substituted p-phenylenediamine color developer
US4113491A (en) * 1975-02-10 1978-09-12 Konishiroku Photo Industry Co., Ltd. Color photographic developing composition

Also Published As

Publication number Publication date Type
FR822269A (en) 1937-12-24 grant
GB481275A (en) 1938-03-08 application
DE767652C (en) 1953-03-02 grant

Similar Documents

Publication Publication Date Title
US3632345A (en) Photographic material using splittable couplers
US3432300A (en) 6-hydroxy chromans used as stabilizing agents in a color photographic element
US3342597A (en) Color developer precursor
US3582322A (en) Color photographic elements and process
US3558319A (en) Color photographic silver halide emulsion containing magenta couplers
US3843371A (en) Photographic material stabilised against the deleterious effects of ultraviolet radiation
US3933501A (en) Photographic elements containing color-forming couplers having and inhibiting effect upon the reactivity of competing couplers
US4401752A (en) Aryloxy substituted photographic couplers and photographic elements and processes employing same
US2322015A (en) Dye and photographic emulsion containing the same
US3260597A (en) Photographic multicolor diffusion transfer process using dye developers and development arrestors
US3141771A (en) Aldehyde scavengers for photographic silver halide developers
US4556630A (en) Color photographic light-sensitive material
US2274782A (en) Light-sensitive photographic material
US4587195A (en) Method of processing silver halide photographic light-sensitive material
US2407210A (en) Color couplers
US2487569A (en) Antistain baths for color photographic materials
US3706561A (en) Compositions for making blixes
US4220711A (en) Silver halide color photographic light-sensitive element
US5278034A (en) Process for forming color image
US4892804A (en) Photographic color developing compositions which are especially useful with high chloride photographic elements
US2474293A (en) 1-naphthol-2-carboxylic acid amide couplers for color photography
US3764337A (en) Color photographic materials containing dihydroxyspirochroman compounds as stabilizers
US3961959A (en) Process for developing a light-sensitive silver halide photographic material
US2875057A (en) Benzoylacet-o-alkoxyanilide couplers for color photography
US2735765A (en) Ch-chs