US2271230A - Sulphonamides of dyes - Google Patents

Sulphonamides of dyes Download PDF

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Publication number
US2271230A
US2271230A US355092A US35509240A US2271230A US 2271230 A US2271230 A US 2271230A US 355092 A US355092 A US 355092A US 35509240 A US35509240 A US 35509240A US 2271230 A US2271230 A US 2271230A
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United States
Prior art keywords
dye
gelatin
sensitive
dyes
group
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Expired - Lifetime
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US355092A
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English (en)
Inventor
Willard D Peterson
Weissberger Arnold
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Eastman Kodak Co
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Eastman Kodak Co
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    • 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
    • G03C1/00—Photosensitive materials
    • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
    • G03C1/83—Organic dyestuffs therefor

Definitions

  • This invention relates to sensitive photographic materials having coloring matters therein.
  • Coloring matters are requiredin sensitive photographic materials for many purposes. Thus, it is often necessary to incorporate in photographic emulsions coloring matters to act as filters or to serve for the production of colored images by difierential bleaching in the image and nonimage. areas. Coloring matters may be introduced into emulsion layers or into grains. of silver halide emulsion disposed in ,a carrier, or into the,carrier for such grains, especially in the case of elements for color photography having two or more layers or sets of grains on oneor-more supports. Furthermore, coloring matters may be present in layers other than those containing the-sensitive silver halide, e. g. in filter layers over or under sensitive emulsion layers or between two sensitive emulsion layers or in backing serving, for example, as anti-halation layers.
  • coloring matters which will not difiuse during coating nor during the processing of the materials. Since, in the processing, acid oralkaline baths may be used it may be necessary to use coloring matters which are resistant to either acid or alkali or both. Numerous coloring matters for these purposes have been proposed in the past, but it is always a matter of difliculty to avoid their diffusion from the place where they are required to be present.
  • the coloring matter is one which contains free aromatic aminoor hydroxyl groups, it may give rise to stains when the element containing it is subjected to the action of a color developer, due presumably to the formation of an indophenol of indamine.
  • coloring matters to employ in photographic elements for any of the purposes indicated are those containing a sulphonylamide group, especially those in which both hydrogen atoms on the amido nitrogen atom are substituted by organic radicals.
  • Such coloring matters are represented by either of the formulae.
  • N-SOr-Y D a dye portion, that is, the residue of a coloring matter
  • X and Y alkyl or aryl, which may be substituted or unsubstituted element made according to one modification of I our invention
  • I Fig. 2 is a sectional view of a photographic element made according to another modification of our invention.
  • Example 1 solutions It may be used as a yellow dye in a bleach-out process using acid bleaching baths for diiferential bleaching in the image or nonimage areas.
  • Example 4 Dyes according to our invention may also be made by generating an azomethine or indophenol dye containing a sulphonamide. group in'the gelatin itself.
  • This example illustrates a method of developing a dye ofv the indophenol type in gelatin by the use of a coupler which can be easily dispersed in gelatin by virtue of a di-substituted sulphonamide group'in its molecule.
  • an indophenol dye may be formed from 2-chloro-5-(fi-naphthalenesulphonbenzylamido) -1-naphthol and 2-amino-5-diethylaminotoluene hydrochloride forming a dye of the following composition:
  • Such a dyed gelatin solution may be used as an antihalation or filter layer, or it may be mixed with silver 7 halide emulsion and used in a light-sensitive lay- .be extended to the production of dyes of the azo and azomethine types by starting with couplers having sulphoamide groups which permit their uniform dispersion in gelatin.
  • These gelatinazonium salt solutions in order to generate azo dyes or with p-phenylenediamine compounds containing a free amino group with a mild oxidizing agent to generate azomethine dyes;
  • the advantage of this method lies in the fact that the dye itself would be dispersed with difficulty whereas the coupler of smaller molecular weight can be readily dispersed uniformly in the gelatin.
  • Example 6 An azomethine dye is made from cyanoacetylcoumarone-sulphon-N-amplanilide and 2-amino- 5-diethylaminotoluene hydrochloride, having the following composition:
  • Example 7' An azomethine dye is made from'igyanoacetylc'oumarone-x-sulphon-N-n-amyl-p-tertiary amyl anilide and 2-amino- 5-diethylaminotoluene hydrochloride, having the following composition:
  • sulphonamide couplers are used which may be considered as having been derived from a secondary amine, that is, the 5111- phonamide group is substituted with allwl or aryl radicals. Couplers of this type are described in sensitive and the green-sensitive layers, a gela- Weissberger U. S. application Ser. No. 253,669, filed August 22, 1940.
  • I0 is a support or any suitable transparent material such as glass, cellulose ester or synthetic resin having thereon a sensitive emulsion layer II.
  • a gelatin layer 12 containing a dye having a iii-substituted sulphonamide group made according to our invention.
  • Fig. 2 illustrates a multidayer element having a support l3 of transparent material such as glass
  • cellulose ester or synthetic resin or opaque material such as paper oropaque cellulose ester.
  • emulsion layers II, II and I6 sensitive, respectively, to diflerent regions of the visible spectrum.
  • gelatin layer II containing a yellow filter dye containing a dilubstituted sulphonamide group according to our invention.
  • the quantity of dye used in the filter and antihalation layers made according to our invention may vary according to the tinctorial strength of the dye and the optical density desired.
  • An average quantity of dye is about 2-5 grams per liter of 10% gelatin solution.
  • a light-sensitive photographic element including a filter layer comprising gelatin having therein a non-diffusing dye having a general formula selected from the class consisting of lution on a photographic support. WILLARD hydrogen atoms are replaced with aryl nuclei.
  • a photographic element comprising a support having thereon three emulsion layers sensitive respectively to the red, green, and blu regions of'the spectrum, and between the bluetin filter layer containing a d-amino-azobenzene in which one of the hydrogen atoms of the amino group is replaced with an aromatic sulphonyl roup and the other hydrogen atom is replaced with a substituted alkyl group.
  • a photographic element comprising a support having thereon three emulsion layers sensitive respectively to the red, green, and blue regions or the'spectrum, and between the bluesensitive and the green-sensitive layers, a gelatin filter layer containing a 4-amino-azobenzene in which one 01 the hydrogen atoms of the amino group is replaced with ana'romatic sulphonyl group and the other hydrogen atom is replaced with a' benzyl group.
  • the method or making a photographic filter layer which comprises mixing with a gelatin solution a primary aromatic amino developing agent and a sulphonamide coupler derived from a secondary amine and containing a group reactive with the oxidation product of said developin azent. mixing an oxidizing agent with said gelatin solution to oxidize said developing agent and produce a dye with said sulphonamide coupler, and coating the dye-containing gelatin so- D.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
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US355092A 1939-09-07 1940-08-31 Sulphonamides of dyes Expired - Lifetime US2271230A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2271230X 1939-09-07

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US2271230A true US2271230A (en) 1942-01-27

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US (1) US2271230A (fr)
FR (1) FR53119E (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2453661A (en) * 1944-05-03 1948-11-09 Eastman Kodak Co Colored couplers
US2455169A (en) * 1944-05-03 1948-11-30 Eastman Kodak Co Colored couplers
US2455170A (en) * 1944-05-03 1948-11-30 Eastman Kodak Co Colored couplers
US2584349A (en) * 1944-11-10 1952-02-05 Gen Aniline & Film Corp Color forming development with an aromatic primary amino developer and alpha-[4-sulfophenylazo]-aceto-acet-2-4-dichloroanilide
US2687957A (en) * 1948-12-08 1954-08-31 Gen Aniline & Film Corp Light-sensitive photographic elements containing azo pyrazolones bleachable in ferricyanide compositions

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2453661A (en) * 1944-05-03 1948-11-09 Eastman Kodak Co Colored couplers
US2455169A (en) * 1944-05-03 1948-11-30 Eastman Kodak Co Colored couplers
US2455170A (en) * 1944-05-03 1948-11-30 Eastman Kodak Co Colored couplers
US2584349A (en) * 1944-11-10 1952-02-05 Gen Aniline & Film Corp Color forming development with an aromatic primary amino developer and alpha-[4-sulfophenylazo]-aceto-acet-2-4-dichloroanilide
US2687957A (en) * 1948-12-08 1954-08-31 Gen Aniline & Film Corp Light-sensitive photographic elements containing azo pyrazolones bleachable in ferricyanide compositions

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Publication number Publication date
FR53119E (fr) 1945-09-19

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