US2286838A - Photographic element containing a disazo dye - Google Patents

Photographic element containing a disazo dye Download PDF

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Publication number
US2286838A
US2286838A US382978A US38297841A US2286838A US 2286838 A US2286838 A US 2286838A US 382978 A US382978 A US 382978A US 38297841 A US38297841 A US 38297841A US 2286838 A US2286838 A US 2286838A
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Prior art keywords
dye
nucleus
dyes
layer
groups
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US382978A
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English (en)
Inventor
Merrill W Seymour
Chechak Jonas John
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to FR956693D priority Critical patent/FR956693A/fr
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Priority to US382978A priority patent/US2286838A/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/28—Preparation of azo dyes from other azo compounds by etherification of hydroxyl groups
    • 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
    • G03C1/831—Azo dyes

Definitions

  • This invention relates to a photographic element and more particularly to a single or multilayer photographic element wherein at least one of the layers is uniformly colored with a dye selected from the group of disazo compounds having the general formula:
  • R represents a member selected from the group consisting of a naphthalene disulfonic acid nucleus, a dibenzyl disulfonic acid nucleus, a diphenyl disulfonic acid nucleus, a di-tolyl disulfonic acid nucleus, a stilbene disulfonic acid nucleus, and a diphenyl urea disulfonic acid nucleus
  • R1 and R2 each represents a saturated alkyl group having a chain length of at V least 3 carbon atoms and not greater than 5 carbon atoms.
  • the nuclei of R can be further substituted by one or more monovalen't substituents selected from the group including methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy methoxymethyl, methoxyethyl, chlorine, bromine, and the like groups.
  • chrysophenine G wherein R1 and R2 are ethyl groups, difiuses very badly from one photographic gelatin layer to another, whereas the various corresponding propyl, butyl and amyi substituents are completely or almost completely non-diffusing. While the corresponding higher alkyl members, that is, those of greater than 5 carbon It is well known in the photographic art that dyes used in photographic layers such as filter dyes, antihalation dyes and image-forming dyes should remain fixed in the layers wherein they are incorporated.
  • atom chain lengths are likewise non-diffusing, we have found them unsuitable, because of difficulty of incorporating them into the compositions from whichour photographic layers are formed, and because of difficulty of bleaching these dyes to form photographic images. Moreover, the dyes with more than 5 carbon atoms in the alkyl chains are more expensive to manufacture.
  • Another object is to provide image-forming dyes for color photography which have the proper spectral ab- Other objects will appear from the following description of our invention.
  • disazo dyes which can be prepared by tetrazoting symmetrical aromatic diainines such as 4,4'-diamino-stilbene-2,2'-disulfpnic acid, 'benzidine-3,3'-disulfonic acid, tolidine disulfonic acids, 1,5-diamino-naphthalene disulfonic acids, 4,4'-diamino-dibenzyl disulfonic acid, 4,4-diamino-3,3'-disulfo-diphenyl urea, and the like, and coupling with 2 moles of phenol or its substitution products and convertonly on the type of dye and upon the molecular size, but also upon the chain-length of the specific substituents.
  • symmetrical aromatic diainines such as 4,4'-diamino-stilbene-2,2'-disulfpnic acid, 'benzidine-3,3'-disulfonic acid, tolidine disulfonic acids, 1,5
  • Example 1 The dye madeby' tetrazotizing 1 mole of 4,4-
  • isopropyl, butyl and amyl ethers there can be employed the corresponding isopropyl, butyl and amyl ethers.
  • Example 3 The dye made by tetrazotizing 1- mole of toli- I dine disulfonic acid and coupling in an alkaline medium with 2 moles of phenol and then converting tothe sec.-butyl ether having the following structure:
  • Example 4 The dye made by tetrazotizing 1 mole of 1,5-diamino-naphthalene disulfonic acid and coupling,
  • NHC ONH- N NOO cin- S OzNa
  • Example 7 The dye made by tetrazotizing 1 mole of o-tolidine disulfonic acid and coupling in an alkaline medium with 2 moles of 2-chloro-5-hydroxy toluene. and then converting to the n-prcpyl ether
  • the dyes above described can be employed in filter overcoats, overcoats or interlayers in photographic films, plates or paper, or, they may be mixed with unsensitized or optically sensitized emulsions and employed in the preparation of films for color processes, in which the image is formed by destruction of a portion of a. uniform port having thereon a light-sensitive layer, at
  • the dyes which we have described may be used in a photographic material such as that described in Christensen U. S. Patent No. 1,517,049, issued November 5, 1924.
  • the sensitive layers are uniformly colored a color complementary to that which they are designed to record.
  • the blue-sensitive layer is colored yellow
  • the green-sensitive layer is 001-.
  • the red-sensitive layer is colored blue-green.
  • the dyes usedaccording to our invention may also be incorporated in layers which are sensitive to any color.
  • the dyes proposed according to our invention all of which are yellow, may be incorporated in a green-sensitive layer or a redsensitive layer as well as in a bluesensitive layer of a multi-layer coating.
  • the sensitive compositions containing our dyes may be coated on transparent film supports such as a derivative of cellulose including cellulosenitrate, cellulose acetate, cellulose propionate, cellulose butyrate, cellulose acetatepropionate, cellulose acetate-butyrate, cellulose ether, and the like, as well as on a synthetic resin support such as a polyvinyl acetal, and opaque supports such as paper or cellulose derivatives mixed with.opaque white pigments.
  • 'I'hey may be used in single layer or ,multi laye'r coatings ,or inmulti-layer coatings onone or both sides of a support.
  • the'dyes we propose to use may be bleached in suitable alkaline bleaching solutions such as sodium stannite.
  • the dye may be bleached in the presenceof a. silver salt image which is converted to a silver image in the same operation.
  • Dyes 'ofthe structure which we have described are practically non-difi'using in gelatin, and have little or no adverse effect on the sensitivity of the emulsionin which they are incorporated or on adjacent emulsion layers. They may be bleached in the presence of a silver. or silver salt image as stated above and whenused in filter layers, they may be discharged by the useof sodium hydrosulfite or potassium permanganate and acid.
  • the dyes which we have proposed have good water solubility, thus facilitating the preparation of dyed layers of adequate dye density without crystallization of the dye.
  • dyes may contain various monovalent substituents, it should be noted that the solubilizing groups are limited in number to avoid too great a tendency to 'diifuse, For example, some non-difiusable dyes can he made to diffuse by introducing an excessive munber of sulfonic acid groups into the dye molecule.' This fact is well known in the dye art and we do not intend to include within the scope of our invention dyes containing an excess number of soluoilizing groups which increase the diffusion tendency. In general, dyes of the types described in our invention are satisfactory with two suli'onic acid groups in the molecule, but may difluse with a greater number of sulfonic groups.
  • a photographic element comprising a supleast one layer comprising a water-permeable colloid and a dye having the general formula:
  • R represents a member selected from the group consisting of a naphthyl nucleus, a dibenzyl nucleus, a diphenyl nucleus, a diphenyl OR! OR: wherein R represents a' stilbene nucleus, and R;
  • R2 each represents a member selected from the group consisting of saturated alkyl groups of from 3 to 5 carbon atoms, and wherein the stilbene nucleus contains two sulfonic acid groups as nuclear substituents.
  • A' photographic element comprising a support having thereon a light-sensitive layer, at least one layer comprising "a water-permeable colloid and a dye having'the general formula:
  • R represents a diphenyl nucleus
  • R represents a naphthalene nucleus
  • R1 and R each represents a member selected from the group consisting of saturated alk'yl groups of from 3 to 5 carbon atoms, and wherein the said naphthalene nucleus contains two sulfonic acid groups as nuclear substituents.
  • a photographic element comprising a support having-thereon a light-sensitive layer, at
  • At least one layer comprising a water-permeable colloid and a dye having the general formula:
  • R1 and R2 each represents a member selected from the group consisting of saturated alkyl groups of from 3 to 5 carbon atoms.
  • a photographic element comprising a support havingthereon a light-sensitive layer, at
  • At least one layer comprising a water-permeable colloid and a dye having the formula:
  • R represents a member selected from the group consisting of a naphthyl nucleus, a dibenzyl nucleus, a diphenyl nucleus, a diphenylurea nucleus, and a stilbene nucleus
  • R1 and R2 each represents a member selected from the group consisting'of saturated alkyl groups of from 3 to 5 carbon atoms, and wherein the said nuclei contain two sulfonic acid' groups asrnuclear substituents.
  • R1 and R2 each represents a member selected from the group consisting of saturated alkyl groups of from 3 to 5 carbon atoms, and wherein the stilbene nucleus contains two sulfonic acid groups as nuclear substituents.
  • R represents a diphenyl nucleus
  • R1 and R2 each represents. a member selected from the group consisting of saturated alkyl groups of from 3 to 5 carbon atoms, and wherein the said diphenyl nucleus contains two sulfonic acid groups as nuclear substituents.
  • R represents a naphthalene nucleus
  • R1 and R2 each represents a member selected QDENOO cmcnlcm from the group consisting of saturated alkyl groups of from 3 to 5 carbon atoms, and wherein the said naphthalene nucleus contains two sulfonic acid groups as nuclear substituents.
  • R1 and R2 each represents a'member selectedv from the group consisting of saturated alkyl groups of from 3 to 5 carbon atoms.
  • a photographic element comprising a support having thereon a light-sensitive layer, at least one layer comprising gelatin and a dye having the general formula:

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US382978A 1941-03-12 1941-03-12 Photographic element containing a disazo dye Expired - Lifetime US2286838A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
FR956693D FR956693A (en, 2012) 1941-03-12
US382978A US2286838A (en) 1941-03-12 1941-03-12 Photographic element containing a disazo dye

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US2286838A true US2286838A (en) 1942-06-16

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2420631A (en) * 1941-08-19 1947-05-13 Eastman Kodak Co Dis-azo dyes for color photography
US2583076A (en) * 1946-08-23 1952-01-22 Technicolor Motion Picture Imbibition printing using disazo dye
US3467522A (en) * 1965-03-19 1969-09-16 Agfa Gevaert Ag Photographic material for the silver dye bleach process
US4612369A (en) * 1978-06-30 1986-09-16 Ciba-Geigy Corporation Disazo 4,4'-diaminostilbene-2,2'-disulfonic acids dye

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2420631A (en) * 1941-08-19 1947-05-13 Eastman Kodak Co Dis-azo dyes for color photography
US2583076A (en) * 1946-08-23 1952-01-22 Technicolor Motion Picture Imbibition printing using disazo dye
US3467522A (en) * 1965-03-19 1969-09-16 Agfa Gevaert Ag Photographic material for the silver dye bleach process
US4612369A (en) * 1978-06-30 1986-09-16 Ciba-Geigy Corporation Disazo 4,4'-diaminostilbene-2,2'-disulfonic acids dye

Also Published As

Publication number Publication date
FR956693A (en, 2012) 1950-02-02

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