US3455693A - Mordants for use in dyed filter layers - Google Patents

Mordants for use in dyed filter layers Download PDF

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US3455693A
US3455693A US479762A US3455693DA US3455693A US 3455693 A US3455693 A US 3455693A US 479762 A US479762 A US 479762A US 3455693D A US3455693D A US 3455693DA US 3455693 A US3455693 A US 3455693A
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dye
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Donald W Heseltine
Dugald A Brooks
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Eastman Kodak Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C07D213/20—Quaternary compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C07D215/10—Quaternary compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/84—Naphthothiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D293/00—Heterocyclic compounds containing rings having nitrogen and selenium or nitrogen and tellurium, with or without oxygen or sulfur atoms, as the ring hetero atoms
    • C07D293/02—Heterocyclic compounds containing rings having nitrogen and selenium or nitrogen and tellurium, with or without oxygen or sulfur atoms, as the ring hetero atoms not condensed with other rings
    • C07D293/04—Five-membered rings
    • C07D293/06—Selenazoles; Hydrogenated selenazoles
    • 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
    • G03C1/835—Macromolecular substances therefor, e.g. mordants
    • 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
    • G03C8/00—Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
    • G03C8/42—Structural details
    • G03C8/52—Bases or auxiliary layers; Substances therefor
    • G03C8/56—Mordant layers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/142—Dye mordant

Definitions

  • a bulky quaternary nitrogen heterocyclic alkali-release mordant that under alkaline conditions form betaines that will not mordant anions, is advantageously used as a mordant for a water-soluble acid dye and hydrophilic colloid light-adsorbing and light-filtering layers of photographic elements where it is desired to firmly hold the acid dye until photographic processing when during treatment in the alkaline processing solutions the acid dye is completely released and the betaines formed of the mordant is incapable of remordanting the acid dye or thiosulfate ions from the fixing bath.
  • This invention relates to certain bulky, i.e., relatively high molecular weight, quaternary nitrogen heterocyclic compounds which function as alkali-releases mordants, to photographic materials and more particularly to photographic elements containing these compounds in light-screening and light-absorbing layers, and to methods for their preparation.
  • Such dye-mordant lightscreening salt may be in a layer overlying a light-sensitive emulsion or overlying two or more light-sensitive emulsions; or it may be in a light-sensitive emulsion for the purpose of modifying a light record in such emulsion or for protecting an overlying light-sensitive emulsion or emulsions from the action of light of wavelengths absorbed by such light-screening substance, or it may be in a layer not containing a light-sensitive substance but arranged between two light-sensitive emulsions; or it may be in a layer serving as a backing on an element having one or more light-sensitive emulsions (for example, to reduce halation).
  • light-screening substances are often required (a) in overcoatings upon photographic elements to protect the light-sensitive emulsion or emulsions from the action of light which it is not desired to record, (b) -in layers arranged between differentially color sensitized emulsions, e.g., to protect redand green-sensitive emulsions from the action of blue light, and (c) in backings forming the so-called antihalation layers on either side of a transparent support carrying the light-sensitive emulsion or emulsions.
  • the element contains a color sensitized emulsion or color sensitized emulsions
  • lightscreening substances which can readily be rendered ineffective, i.e., decolorized or destroyed and removed prior 3,455,693 Patented July 15, 1969 ice to or during or after photographic processing.
  • mordants Numerous substances have been proposed as mordants to prepare the dye-mordant salts used as light-screening and light-absorbing materials for the purposes indicated above.
  • the proposed mordants are relatively high molecular weight compounds having ionic charges opposite to those of the particular light-absorbing dye.
  • the dye employed might be an acid dye, in which case the mordant would be a cationic compound.
  • Typical of such proposed mordants are, for example, derived polymers such as the basic reaction products of polyvinylsulfonates and C-aminopyridines as described in D. D. Reynolds, et al., US. Patents 2,701,243 and 2,768,078, granted, Feb. 1, 1955, and Oct. 23, 1956, respectively.
  • hydrophilic materials such as gelatin and readily form substantially non-ditfusible salts with water-soluble acid dyes.
  • they have a molecular weight of about at least 300, although polymeric materials having a molecular weight of 600 to 50,000, and higher, have been found to be particularly useful in our invention.
  • an object of the invention to provide a light-sensitive photographic element having one or more layers containing at least one novel and nonditfusible salt of certain novel quaternary nitrogen heterocyclic mordants with a water-soluble acid dye. Another object is to provide a light filter layer containing at least one of the above salts; which layer may be coated between two or more silver halide emulsion layers in a multilayer element. Another object is to provide a lightsensitive gelatino-silver halide layer containing at least one of the above salts.
  • Another object is to provide photographic elements with an overcoating and/or a backing layer which contain(s) at least one novel non-diffusing salt of certain novel quaternary nitrogen heterocyclic mordants with water-soluble acid dyes.
  • R represents an alkyl group having typically from 1 to 18 carbon atoms (e.g., methyl, ethyl, propyl, butyl, hexyl, benzyl, phenethyl, decyl, dodecyl, octadecyl, etc.), or an aryl group (e.g., phenyl, tolyl, naphthyl, diphenyl, terphenyl, etc.), or an amino or substituted amino group (e.g., amino, dimethylamino, anilino, etc.), or a linear polymeric structure, for example, an addition type polymer such as a polymer of a monoethylenically unsaturated polymerizable compound having periodically occurring groups of the structure:
  • a monomethylenically unsaturated polymer e.g., a polyvinyl ester or alkyl ketone, 21 polyisopropenyl ester or alkyl ketone;
  • R represents the hydrogen atom, a lower alkyl group (e.g., methyl, ethyl, etc.), or a phenyl group;
  • R represents the hydrogen atom, an alkyl group (e.g., methyl, ethyl, propyl, isopropyl, butyl, hexyl, dodecyl, pentadecyl, benzyl, phenethyl, etc.), a hydroxy, a halogen (e.g., chlorine or bromine), or an aryl group (e.g., phenyl, tolyl, biphenylyl, etc.);
  • X represents an acid anion (e.g., chloride, bromide, iod
  • imidazole nucleus e.g., imidazole
  • a benzimidazole nucleus e.g., benzimidazole
  • a naphthimidazole nucleus e.g., 1-alkyl-a-naphthimidazole, 1-aryl-B-naphthimidazole, 1-alkyl-5-methoxy-u-naphthimidazole, etc. a 1,2,4-thiadiazole nucleus,
  • a 1 or 4 alkyl-1,2,4-triazole nucleus e.g., 1-methy1-1,2,4-triazole, 1-butyl-1,2,4-triazo1e,
  • a tetrazole nucleus e.g., tetrazole
  • the new class of bulky quaternary nitrogen heterocyclic compounds of the invention include (1) derived resinous copolymers consisting essentially of not less than 25% by weight of polymerized units of the general structure:
  • R R X and Z are as previously defined, n and m each represents an integrer of from 1 to 2;
  • R represents the hydrogen atom, an alkyl group (e.g., methyl, ethyl, propyl, isopropyl, butyl, hexyl, dodecyl, pentadecyl, benzyl, phenethyl, etc.), a hydroxyl group, a halogen (e.g., chlorine or bromine), or an aryl group (e.g.
  • R represents the hydrogen atom, a lower alkyl group (e.g., methyl, ethyl, etc.), or an aryl group (e.g., phenyl, tolyl, etc.), etc., and wherein the said m, R, R and X stand in each occurrence for the same defined member.
  • the components of Formula II above are so chosen as to give compounds having molecular weights in each instance of at least 300.
  • m, R, R R X and Z are as defined above, under conditions that result in the desired degree of conversion of units of above Formula IV to the corresponding quaternary salts units represented by Formula II(a) above.
  • the preferred starting polymers in the above process are polyvinyl chloroacetate described by Wiley et al., J. Poly. Sci., 3, 708 (1948) or copolymers containing vinyl chloroacetate and vinyl alcohol units prepared by partial esterfication of polyvinyl alcohol with chloroacetic anhydride, and poly(vinyl chloromethyl ketone) prepared, for example, by polymerizing monomeric vinyl chloromethyl ketone (Cath et al., J. Chem. Soc., 1948, p.
  • the reaction is carried out in an inert reaction medium which is a solvent for the starting polymer such as, for example, in acetone, dimethyl sulfoxide, N,N-dimethylformamide, 'y-butyrolactone, etc.
  • the reaction mixture is allowed to stand for several days or more, at room temperatures or heated for several hours.
  • the quaternary salt product which forms is isolated by precipitation into a nonsolvent for salt product, or in the case where the salt product forms as a precipitate in the reaction mixture, the supernatant liquor can be simply decanted.
  • the quaternary salt product can then be further purified by washing with a nonsolvent and dried preferably under vacuum.
  • the quaternary salt products consisting from about 25-100% by weight of quaternized units and from 750% by weight of unquaternized residual units have been found to be especially eflicacious mordants in photographic layers and are preferred.
  • Formula III compounds can be prepared by reacting a compound having the general formula:
  • n, R and R are as previously defined, with a mixture of a tertiary amine of Formula V above and a halogen such as chlorine, bromine or iodine, preferably in about the molar ratios of 12121 of the compounds of Formula VII, Formula V and halogen, respectively.
  • a nonsolvent e.g. acetone
  • the above defined polymeric mordants of the invention function as alkali-release mordants.
  • they form betaines so as to lose their ability to act as a mordant with release and subsequent removal of the mordanted dye from the system.
  • the bulky quaternary nitrogen compound which under acid or neutral conditions is capable of salt formation with an acidic dye may under alkaline conditions release the dye by decomposition of the mordant to separate the quaternary nitrogen fragment from the bulky residue or by a rearrangement reaction to produce a zwitterion with resultant internal charge compensation or by the loss of the quaternary nature of the nitrogen.
  • a major advantage of the above 7 alkali release mordants is, therefore, that the compounds do not retain either the previously mordanted dye or thiosulfate ion from the fixing bath after processing, as do other compounds of similar mordanting ability providing a neutral or mildly alkaline hypo bath is used.
  • the photographic elements prepared with the abovedescribed polymeric and non-polymeric mordants of the invention comprise a support material having thereon at least one hydrophilic colloid layer containing a mordant of the invention, which layer may also contain a lightsensitive silver halide.
  • the preferred light-sensitive photographic elements comprise a support having thereon at least one hydrophilic colloid layer containing a mordant of the invention and at least one light-sensitive silver halide emulsion layer.
  • the mordant containing light-screening and antihalation layers are customarily prepared by coating on the support or photographic element by methods well known in the art, a water solution comprising at least one mordant of the invention, an acid dye, a water-permeable hydrophilic colloid binder and a coating aid such as saponin.
  • a water solution comprising at least one mordant of the invention, an acid dye, a water-permeable hydrophilic colloid binder and a coating aid such as saponin.
  • the pH of the coating solution is adjusted when necessary to a level that is compatible with the light-sensitive emulsion layer by the usual methods.
  • Suitable support materials include any of those used in photography such as cellulose acetate, cellulose propionate, cellulose acetate-butyrate, cellulose nitrate, synthetic resins such as nylon, polyesters, polystyrene, polypropylene, etc., paper, and the like.
  • Suitable hydrophilic colloid materials that can be used in the mordant containing compositions and layers, and photographic elements, of the invention include gelatin, albumin, collodion, gum arabic, agar-agar, cellulose derivatives such as alkyl esters of carboxylated cellulose, hydroxy ethyl cellulose, carboxy methyl hydroxy ethyl cellulose, synthetic resins, such as the amphoteric copolymers described by .Clavier et al. in U.S. Patent 2,949,442, issued Aug. 16, 1960, polyvinyl alcohol, polyvinyl pyrrolidone, and others well known in the art.
  • the abovementioned amphoteric copolymers are made by polymerizing the monomer having the formula:
  • R represents an atom of hydrogen or a methyl group, and a salt of a compound having the general formula:
  • R has the above-mentioned meaning, such as an alkylamine salt.
  • These monomers can further be polymerized with a third unsaturated monomer in an amount up to about 20 percent, and preferably from -15 percent, of the total weight of monomer used, such as an ethylene monomer that is copolymerizable with the two principal monomers.
  • the third monomer may contain either a. basic group or an acid group and may, for example, be vinyl acetate, vinyl chloride, acrylonitrile, methacrylonitrile, styrene, acrylates, methacrylates, acrylamide, methacrylamide, etc.
  • polymeric gelatin substitutes examples include copolymers of allyla-mines and methacrylic acid; copolymers of allylamine, acrylic acid and acrylamide; hydrolyzed copolymers of allylamine, methacrylic acid and vinyl acetate; the copolymers of allylamine, acrylic acid and styrene; the copolymers of allylamine, methacrylic acid and acrylonitrile; etc.
  • the dyes that can be effectively mordanted in accordance with our invention include any filter dye that has one or more acidic group substituents such as sulfo or carboxyl groups, for example, the oxonol dyes described and claimed in copending application of Joseph Bailey, Ser. No. 98,709, filed Mar. 27, 1961, now Patent No. 3,247,127, having the formula:
  • Z represents the nonmetallic atoms necessary to complete a l-carboxyalkyl 3 hydrocarbon substituted hexahydro-2,4,6-trioxo-S-pyrimidine nucleus, 11 in each case is an'integer of from 1 to 3, each R represents a carboxyalkyl group in which the carboxy substituent is attached to an alkyl group having from 1 to 2 carbon atoms, R is an alkyl group of from 1 to 8 carbon atoms or an aryl group such as phenyl or an alkyl or alkoxy substituted phenyl group, and X is hydrogen or an alkyl group of from l to 4 carbon atoms, such that no more than one X is an alkyl group.
  • Suitable acid dyes include the benzoxazolepyrazolone merocyanine dyes described in copending application of Jones et al. U.S. Ser. No 167,666, filed J an. 22, 1962, now Patent No. 3,282,- 699, having the formula:
  • R7 represents an alkyl group such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertiary butyl, etc., or a carboxyalkyl group, such as carboxymethyl, carboxyethyl, carboxypropyl, etc., or a sulfoalkyl group, such as sulfoethyl, sulfopropyl, sulfobutyl, etc.;
  • Z represents the nonmetallic atoms necessary to complete a heterocyclic nucleus of the benzoxazole series (including benzoxazole and benzoxazole substituted with substitutions such as methyl, ethyl, phenyl, methoxy, ethoxy, chlorine, bromine, etc.) or a nucleus of the benzoxazole series which has a sulfo-substituent 0n the benzene ring as well as one or
  • Z represents the sulfo-substituted benzoxazole nucleus and when R represents a carboxyalkyl group or a sulfoalkyl group, Z represents the nonmetallic atoms necessary to complete a benzoxazole nucleus; Q represents the nonmetallic atoms necessary to complete a heterocyclic nucleus of the sulfophenyl pyrazolinone series and n is an integer from 1 to 3.
  • the invention is not limited to just those dyes coming within the general formulas of the above-mentioned copending applications, since as previously set forth any filter dye containing one or more sulfo or carboxyl groups can be employed.
  • Typical light-filtering dyes include, for example,
  • trioxo-S-pyrimidine pentamethineoxonol
  • typical ultraviolet absorbing dyes include the 2,5- bis(substituted sulfophenyl) thiazolo[5,4 d]thiazole disodium salts of Sawdey U.S. Ser. No. 183,417, filed Mar. 29, 1962, such as 2,5-bis (o-methoXy-x-sulfophenyl)thiazolo[5,4-d]
  • tartrazine and the like filter dyes.
  • Hardening materials that may be used to advantage include such hardening agents as formaldehyde; 2. halogen-substituted aliphatic acid such as mucobromic acid as described in White US. Patent 2,080,019, issued May 11, 1937; a compound having a plurality of acid anhydride groups such as 7,8-diphenyl-bicyclo (2,2,2)-7- octene-2,3,5,6-tetra-carboxylic dianhydride, or a dicarboxylic or a disultonic acid chloride such as terephthaloyl chloride or naphthalene-1,S-disulfonyl chloride as described in Allen and Carroll US.
  • hardening agents as formaldehyde
  • 2. halogen-substituted aliphatic acid such as mucobromic acid as described in White US. Patent 2,080,019, issued May 11, 1937
  • a compound having a plurality of acid anhydride groups such as 7,8-dip
  • a dialdehyde or a sodium bisulfite derivative thereof such as B-methyl glutaraldehyde bis-sodium bisulfite as described in Allen and Burness, Canadian Patent No. 588,451, issued Dec. 8, 1959; a bis-aziridine carboxamide such as trimethylene bis(l-aziridine carboxamide) as described in Allen and Webster U.S. Patent 2,950,197, issued Aug. 23, 1960; or 2,3-dihydroxydioxane as described in Jeifreys U.S. Patent 2,870,013, issued Jan. 20, 1959.
  • a dialdehyde or a sodium bisulfite derivative thereof such as B-methyl glutaraldehyde bis-sodium bisulfite as described in Allen and Burness, Canadian Patent No. 588,451, issued Dec. 8, 1959
  • a bis-aziridine carboxamide such as trimethylene bis(l-aziridine carboxamide) as described in Allen and Webster U.S. Patent 2,950
  • the photographic element utilizing our light-screening layers have light-sensitive emulsion layers containing silver chloride, silver bromide, silver chlorobromide, silver iodide, silver bromoiodide, silver chlorobromoiodide, etc., as the light-sensitive material. Any light-sensitive silver halide emulsion layers may be used in these photographic elements.
  • the silver halide emulsion may be sensitized by any of the sensitizers commonly used to produce the desired sensitometric characteristics.
  • Example 1 Poly(vinyl pyridinium acetate) chloride A. 20 g. (approx. 0.17 mol) of polyvinyl chloroacetate was dissolved in 200 ml. of acetone. Then 40 ml. (approx. 0.47 mol) of pyridine was added and the mixture allowed to stand overnight at room temperature. Soft material had precipitated. The supernatant liquid was decanted. The residue was dissolved in methanol, precipitated in ether, washed, and vacuum dried. It was then redissolved in methanol and reprecipitated in ether, washed, and vacuum dried.
  • this product 0 showed that it contained 2.8% by weight of nitrogen as compared with calculated theory of approximately 7% by weight of nitrogen for pure poly(vinyl pyridinium acetate) chloride. Accordingly, this derived polymer consisted essentially of about 40% by weight of recurring (vinyl pyridinium acetate) chloride units of the structure:
  • Example 2 A solution of 60.0 (approx. 0.57 mol) of poly(vinyl chloromethyl ketone) in 600 ml. of N,N-dimethylformamide was treated with ml. (approx. 1.58 mol) of pyridine. The mixture was allowed to stand for 6 days. A soft precipitate formed. The supernatant liquor gave no precipitate in ether and discarded. The residue was disand the remainder of the polymer molecule to make 100% of recurring units of unreacted vinyl chloromethyl ketone.
  • Example 3 To 10 cc. of 10% photographic gelatin melted at C. was added 30 mg. of poly(vinyl pyridinium acetate) chloride dissolved in 10 cc. of water. The pH of the solution was adjusted to 4.5-5.0 with glacial acetic acid. To this was added 10 mgs. of his [3-methyl-1-p-sulfophenyl-S-pyrazolone (4) pentamethineoxonol dissolved in water with vigorous stirring. The pH of the melt was then readjusted to :10.1 with 2.5 N sodium hydroxide solution, a coating aid added, the total volume adjusted to 32 cc. with distilled water and the melt coated on a film support and dried.
  • Another portion of the coating was treated in a conventional alkaline silver halide developer solution containing hydroquinone and p-methylaminophenol sulfate as the developing agents.
  • the mordanted dye was completely bleached by this treatment.
  • the coating was treated in a conventional sodium thiosulfate fixing bath and then washed. No residual sodium thiosulfate was detected in the coating by the Ross-Crabtree method.
  • Example 4 shows the use of the derived polymers of the invention as an ultraviolet absorbing overcoating layer over light-sensitive gelatino-silver halide emulsion layers, for example, over the emulsion layers of a multilayer color element of the type described in Mannes et al., US. Patent 2,252,718, issued Aug. 19, 1941.
  • a gelatin-mordant composition was prepared by mixing 200 g. of a 10% aqueous gelatin solution at 40 C. and 200 g. of a 15% aqueous solution of the polymeric mordant prepared according to Example 1A at 40 C., The clear solution obtained was then chilled, noodled, and washed with cold water in the normal manner for 6 hours, drained, remelted at 50 C. and weighed.
  • a coating melt was then prepared as follows employin g the above gelatin-mordant composition.
  • the sulfur dioxide hydroquinone clathrate is described by H. M. Powell, J. Chem. Soc. (1948), pages 61-73- CA. 42, 5293 (1948).
  • This melt was then coated over the emulsion layers of the above-mentioned multilayer color element at 6 g./sq. ft. (containing 1.33% gelatin) to give a coating comprising 120 mg./sq. ft. of the polymeric mordant of Example 1 and 40 mg./sq. ft. of the filter dye in mg./sq.
  • Our alkali-release polymeric mordants are also used to advantage in mordanting light-filtering dyes, such as a blue-light absorbing dye having one or more acid substituents, in a filtering layer between the top blue-sensitive layer and over the green-sensitive and the red-sensitive layers of a multilayer color photographic element of the type described in Mannes et al US. Patent 2,252,718, referred to previously.
  • appropriate dyes of other colors can be used to advantage in mordanted filter layers between the green-sensitive and red-sensitive layers, or one or more appropriate dyes can be mordanted in an antihalation layer either. between the light-sensitive layers and the support or on the side of the support away from the light-sensitive layers.
  • Examples 5 through 8 illustrate the use of the derived polymeric mordants of the invention in antihalation layers, and further illustrate the improvement obtained therewith in regard to hypo retention in the processed elements, as compared with an element prepared with a known mordanting polymer and a non-mordanted control element.
  • the coating melts Were prepared, in general, .by the procedure described in above Example 4.
  • the melt compositions with the exception of the control example, were coated on an ordinary cellulose acetate film support and over this melt layer was coated in each case a fine-grained silver chlorobromide gelatin emulsion layer.
  • the filter dyes employed are listed as follows:
  • Example 6 A film element was coated having an antihalation undercoat comprising gelatin poly(a-methylallyl-N- guaridylketimine, glycolic acid salt) prepared in accordance with Minsk US. Patent 2,882,156, issued Apr. 14,
  • Dye B 1.6 mg./ft.
  • Dye C 2.9 mg./ft.
  • Dye D 2.5 mg./ft.
  • Example 7 A film element was coated having an antihalation undercoat comprising gelatin and the polymeric mordant of Example 1A (45 mg./ft. Dye A (2.4 mg./ft. Dye B (1.6 mg./ft. Dye C (2.9 mg./ft. and Dye D (2.5 mg./ft.
  • Example 8 A film element was coated having an antihalation undercoat comprising gelatin and the polymeric mordant of Example 1A (45 mg./ft. Dye E (5 mg./ft. Dye F (5 mg./ft. and Dye G (5 mg./ft.
  • This compound forms the yellow betaine upon treatment with alkali with a resultant internal charge com pensation as follows: 4
  • This compound at a ratio of 5 parts by weight to 1 part by weight of dye, mordanted the dye bis[3-methyllp-sulfophenyl-S-pyrazolone-(4) ]-pentamethine oxonol in gelatin with no bleeding upon washing in water.
  • the mordanted dye was bleached in a developer having the composition:
  • Example 10.-4-benzyl-1-(2-phenylphenacyl pyridinium bromide CaHs 0 A mixture of 1.7 g. (0.01 mol) of 4-benzylpyridine and 2.7 g. (0.01 mol) of 2-bromo-2-phenylacetophenone was heated on the hot plate until the reaction became exothermic. The product was a glass which was chipped out and crushed under ether, washed with ether and collected on a filter and dried. The yield was 4.4 g. of
  • Example y 3/-4-pentadecylphenacyl) pyridinium iodide This compound was prepared by the procedure of above Example 10, except that the reactants were pyridine and 2 hydroxy 4 pentadecylphenacyl iodide. On testing this compound in accordance with the method described in Example 10, it was found to mordant well, to bleach rapidly and to retain no hypo in the aforementioned developer and fixing compositions.
  • FIG. 1 shows light-screening layer 10 comprising gelatin, an acid substituted filter dye and the polymeric mordant of Example 1A, poly(vinyl pyridinium acetate) chloride, coated over a light-sensitive silver halide emulsion layer 11 which is coated on support 12.
  • FIG. 2 shows antihalation layer 15 comprising gelatin, an acid substituted dye and the polymeric mordant of Example 1A, poly(vinyl pyridinium acetate) chloride, coated adjacent to support 16 and a light-sensitive silver halide emulsion .layer 14 coated over layer 15.
  • FIG. 3 shows a multilayer color element comprising a support 21 having a red-sensitive silver halide emulsion layer 20 coated thereon, a green-sensitive silver halide emulsion layer 19 coated over layer 20, a light-screening layer 18 comprising gelatin, an acid substituted dye, and the polymer mordant of Example 1A, poly(vinyl pyridinium acetate) chloride, coated over layer 19, and a blue-sensitive silver halide emulsion layer 17 coated over layer 18.
  • the above mordants are prepared according to the methods of the inventions described in Examples 1 and 2 by reacting polyvinyl chloroacetate
  • mordants of the invention can also be advantageously used in light-screening layers between two or more color sensitized silver halide emulsion layers, or in antihalation backing layers, or incorporated directly in light-sensitive silver halide emulsion layers, or they can be used to prepare imbibition dye transfer blanks of improved properties.
  • a light-sensitive photographic element comprising a support material having thereon at least one hydrophilic colloid layer containing light-sensitive silver halide and at least one hydrophilic colloid layer containing at least one substantially nondiffusible salt of a watersoluble dye with a compound represented by the formula:
  • R represents a member selected from the class consisting of hydrogen, a lower alkyl group and a phenyl group
  • R represents a member selected from the class consisting of hydrogen, an alkyl group and an aryl group
  • X represents an acid anion
  • Z represents the nonmetallic atoms required to complete a nucleus containing a 5- to G-membered heterocyclic ring
  • R represents a member selected from the class consisting of an alkyl group, an aryl group and a polymeric chain of a monoethylenically unsaturated compound having recurring groups of the structure:
  • R in each occurrence represents the same member selected from the class consisting of the hydrogen atom, a lower alkyl group and a phenyl group
  • X in each occurrence represents the same acid anion
  • R represents a member selected from the class consisting of the hydrogen atom, an alkyl group and an aryl group
  • Z represents the nonmetallic atoms required to complete a heterocyclic nucleus selected from the class consisting of a thiazole nucleus, a benzothiazole nucleus, a naphthothiazole nucleus, a thianaphtheno-7',6',4,S-thiazole nucleus, an oxazole nucleus, a benzoxazole nucleus, a napththoxazole nucleus, a selenazole nucleus, a benzoselenazole nucleus, a naph
  • a light-sensitive photographic element comprising a support material having thereon at least one hydrophilic colloid layer containing light-sensitive silver halide and at least one hydrophilic colloid layer containing at least one substantially nonditfusible salt of a water-soluble dye with a compound having the formula:
  • n represents an integer of from 1 to 2
  • R represents a member selected from the class consisting of the hydrogen atom, a lower alkyl group and a phenyl group
  • R represents a member selected from the class consisting of the hydrogen atom, an alkyl group and an aryl group
  • X represents an acid anion
  • Z represents the non-metallic atoms required to complete a heterocyclic nucleus selected from the class consisting of a thiazole nucleus, a benzothiazole nucleus, at naphthothiazole nucleus, a thianaphtheno-7',6',4,S-thiazole nucleus, an oxazole nucleus, a benzoxazole nucleus, a naphthoxazole nucleus, a selenazole nucleus, a benzoselenazole nucleus, a naphthoselenazole nucleus, 2.
  • thiazoline nucleus a quinoline nucleus, an isoquinone nucleus, 2. pyridine nucleus, an imidazole nucleus, a benzimidazole nucleus, a naphthimidazole nucleus, a 3,3-dialkylindolenine nucleus, a 1,2,4-thiadiazole nucleus, a 1,2,4-triazole nucleus, and a tetrazole nucleus, the said compound having a molecular weight of at least 300.
  • a light-sensitive photographic element comprising a support material having thereon at least two hydrophilic colloid layers, at least one of said hydrophilic colloid layers being a silver halide emulsion layer and at least one of said hydrophilic layers containing at least one salt of an acidic dye with a copolymer consisting essentially of from 25-80% by Weight of recurring polymerized units of the structure:
  • m in each occurrence represents the same integer of from 1 to 2
  • R in each occurrence represents the same member selected from the class consisting of the hydrogen atom, a lower alkyl group and a phenyl group
  • X in each occurrence represents the same acid anion
  • R represents a member selected from the class consisting of the hydrogen atom, an alkyl group and an aryl group
  • Z represents the nonmetallic atoms required to complete a heterocyclic nucleus selected from the class consisting of a thiazole nucleus, a benzothiazole nucleus, at naphthothiazole nucleus, a thianaphtheno-7,6',4,5-thiazole nucleus, an oxazole nucleus, a benzoxazole nucleus, a naphthoxazole nucleus, a selenazole nucleus, a benzoselenazole nu
  • a light-sensitive photographic element comprising a support material having thereon at least two hydrophilic colloid layers, at least one of said hydrophilic colloid layers being a silver halide emulsion layer and at least one of said hydrophilic layers containing at least one salt of an acidic dye with a compound having the formula:
  • n represents an integer of from 1 to 2
  • R represents a member selected from the class consisting of the hydrogen atom, a lower alkyl group and a phenyl group
  • R represents a member selected from the class consisting of the hydrogen atom, an alkyl group and an aryl group
  • X represents an acid anion
  • Z represents the nonmetallic atoms required to complete a heterocyclic nucleus selected from the class consisting of a thiazole nucleus, a benzothiazole nucleus, a naphthothiazole nucleus, a thianaphtheno-7',6,4,5-thiazole nucleus, an oxazole nucleus, a benzoxazole nucleus, a naphthoxazole nucleus, a selenazole nucleus, a benzoselenazole nucleus, a naphthoselenazole nucleus, a thiazoline nucleus, a
  • an imidazole nucleus a benzimidazole nucleus, 21 naphth imidazole nucleus, at 3,3-dialkylindolenine nucleus, a 1,2,4-thiadiazole nucleus, at 1,2,4-triazole nucleus, and a tetrazole nucleus, the said compound having a molecular weight of at least 300.
  • a light-sensitive photographic element comprising a support material having coated thereon at least one lightsensitive silver halide emulsion layer and having coated over said emulsion layer a hydrophilic colloid layer containing at least one substantially non-diffusible salt of a water-soluble acid dye with a copolymer consisting essentially of from 25-80% by weight of recurring polymerized units of the structure:
  • m in each occurrence represents the same integer of from 1 to 2
  • R in each occurrence represents the same member selected from the class consisting of the hydrogen atom, a lower alkyl group and a phenyl group
  • X in each occurrence represents the same acid anion
  • R represents a member selected from the class consisting of the hydrogen atom, an alkyl group and an aryl group
  • Z represents the non-metallic atoms required to complete a heterocyclic nucleus selected from the class consisting of a thiazole nucleus, a benzothiazole nucleus, a naphthothiazole nucleus, a thianaphtheno-7',6',4,5-thiazole nucleus, an oxazole nucleus, a benzoxazole nucleus, a naphthoxazole nucleus, a selenazole nucleus, a benzosele
  • a light-sensitive photographic element comprising a support material having coated thereon at least one lightsensitive silver halide emulsion layer and having coated over said emulsion layer a hydrophilic colloid layer containing at least one substantially non-diffusible salt of a water-soluble acid dye with a compound having the formula:
  • n represents an integer of from l to 2
  • R represents a member selected from the class consisting of the hydrogen atom, a lower alkyl group and a phenyl group
  • R represents a member selected from the class consisting of the hydrogen atom, an alkyl group and an aryl group
  • X represents an acid anion
  • Z represents the nonmetallic atoms required to complete a heterocyclic nucleus selected from the class consisting of a thiazole nucleus, a benzothiazole nucleus, a naphthothiazole nucleus, a thianaphtheno-7',6',4,5-thiazole nucleus, an oxazole nucleus, a benzoxazole nucleus, a naphthoxazole nucleus, a selenazole nucleus, a benzoselenazole nucleus, a naphthoselenazole nucleus, a thiazoline nucleus,
  • a light-sensitive photographic element wherein the said copolyrner component of said salt consists essentially of (vinyl pyridinium acetate) chloride units and vinyl chloroacetate units.
  • a light-sensitive photographic element wherein the said resinous copolymer component of said salt consists essentially of (vinyl pyridinium methyl ketone) chloride units and vinyl chloromethyl ketone units.
  • a light-sensitive photographic element wherein at least one of said dye components of said salts is a dye selected from the group consisting of 4 [(3 ethyl 2(3H) benzoxazolylidene)ethylidene]- 3 methyl 1 p sulfophenyl 2 pyrazolin 5 one monosulfonated, bis(1 butyl 3 car-boxymethyl 5- barbituric acid)trimethineoxonol, 4 [4 (3 ethyl- 2'(3H) benzoxazolylidene) 2 butenylidene] 3- methyl 1 p sulfophenyl 2 pyrazolin 5 one monosulfonated, bis(1 butyl 3 carboxymethyl 5 barbituric acid)pentamethineoxonol, bis[3 methyl 1 (psulfophenyl) 2 pyrazolin 5 one (4)]methineoxonol, bis[
  • An element comprising a support material having thereon one hydrophilic colloid layer containing a salt of a water-soluble dye with a compound having the formula:
  • R rep resents a member selected from the class consisting of an alkyl group, and an aryl group
  • R represents a member selected from the class consisting of the hydrogen atom, a lower alkyl group and a phenyl group
  • R represents a member selected from the class consisting of the hydrogen atom, an alkyl group and an aryl group
  • X represents an acid anion
  • Z represents the nonmetallic atoms required to complete a nucleus containing a 5- to 6-membered heterocyclic ring, said compound having a molecular weight of at least 300.

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US4424272A (en) 1981-08-03 1984-01-03 Polaroid Corporation Temporary polymeric mordants and elements containing same
EP0772080A2 (en) 1995-11-02 1997-05-07 Eastman Kodak Company Photographic element useful as a motion picture print film
US6045985A (en) * 1997-12-02 2000-04-04 Tulalip Consultoria Comercial Sociedade Unipessoal S.A. Light-sensitive silver halide photographic elements containing yellow filter dyes
US6903475B2 (en) 2001-02-23 2005-06-07 Black & Decker Inc. Stator assembly with an overmolding that secures magnets to a flux ring and the flux ring to a stator housing

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GB1528616A (en) * 1975-06-04 1978-10-18 Ciba Geigy Ag Alkali-release mordants
DE3305978A1 (de) * 1983-02-21 1984-08-23 Siemens AG, 1000 Berlin und 8000 München Telekommunikationssystem mit abflachung von verkehrsspitzen
GB2140572B (en) * 1983-05-26 1986-06-18 Kodak Ltd Photographic dispersions
US5244994A (en) * 1992-03-20 1993-09-14 Eastman Kodak Company Bleachable polymeric filter dyes
US5470986A (en) * 1994-06-27 1995-11-28 E. I. Du Pont De Nemours And Company Imidazolium hardeners for hydrophilic colloid
GB2552806A (en) * 2016-08-10 2018-02-14 Sumitomo Chemical Co Light filter and sensor

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2675316A (en) * 1949-04-14 1954-04-13 Eastman Kodak Co Photographic elements containing mordants
US2839401A (en) * 1954-12-29 1958-06-17 Du Pont Photographic silver halide emulsions containing copolymeric mordants
US3016306A (en) * 1957-11-25 1962-01-09 Eastman Kodak Co Yellow filter layers for multi-layer photographic color elements
US3271148A (en) * 1962-07-19 1966-09-06 Eastman Kodak Co Mordanting of acid dyes

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2595225A (en) * 1950-02-09 1952-05-06 Du Pont Polymeric poly-quaternary ammonium salts
US2972535A (en) * 1957-09-03 1961-02-21 Eastman Kodak Co Quaternary salts of c-vinylpyridine polymers with compounds containing a haloacetyl group
FR1361293A (fr) * 1962-07-19 1964-05-15 Kodak Pathe Nouvelle composition de mordançage utilisable notamment en photographie

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2675316A (en) * 1949-04-14 1954-04-13 Eastman Kodak Co Photographic elements containing mordants
US2839401A (en) * 1954-12-29 1958-06-17 Du Pont Photographic silver halide emulsions containing copolymeric mordants
US3016306A (en) * 1957-11-25 1962-01-09 Eastman Kodak Co Yellow filter layers for multi-layer photographic color elements
US3271148A (en) * 1962-07-19 1966-09-06 Eastman Kodak Co Mordanting of acid dyes

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4424272A (en) 1981-08-03 1984-01-03 Polaroid Corporation Temporary polymeric mordants and elements containing same
EP0772080A2 (en) 1995-11-02 1997-05-07 Eastman Kodak Company Photographic element useful as a motion picture print film
US6045985A (en) * 1997-12-02 2000-04-04 Tulalip Consultoria Comercial Sociedade Unipessoal S.A. Light-sensitive silver halide photographic elements containing yellow filter dyes
US6903475B2 (en) 2001-02-23 2005-06-07 Black & Decker Inc. Stator assembly with an overmolding that secures magnets to a flux ring and the flux ring to a stator housing

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