US3425834A - Mordants for bleachable filter layers - Google Patents

Mordants for bleachable filter layers Download PDF

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US3425834A
US3425834A US479719A US3425834DA US3425834A US 3425834 A US3425834 A US 3425834A US 479719 A US479719 A US 479719A US 3425834D A US3425834D A US 3425834DA US 3425834 A US3425834 A US 3425834A
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light
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mordants
dye
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Dugald A Brooks
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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
    • 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

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  • This invention relates to certain bulky, i.e., relatively high molecular weight, compounds that contain alkali cleavable, basic nitrogen groups such as alkylamino groups or nitrogen heterocyclic nuclei and function as alkalirelease 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
  • light-screening substances which can readily be rendered ineffective, i.e., decolorized or destroyed and removed prior to or during or after photographic processing. For many purposes it is particularly convenient to employ light-screening substances which are rendered ineffective by one of the photographic baths employed in processing the element after exposure, such as a photographic developing bath or fixing bath.
  • 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 cationic.
  • Typical of such proposed anordants are, for example, derived polymers such Claims ice as the basic reaction products of the 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.
  • an object of the invention to provide a photographic element having one or more layers containing at least one of the bulky basic nitrogen groups containing compounds or salts of the invention described above. Another object is to provide a backing layer containing at least one of these salts. 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 an imbibition blank containing at least one of the above salts. Another object is to provide a light-sensitive gelatino-silver halide layer containing at least one of the above salts. Another object is to provide overcoating layers for photographic elements which contain at least one of the above salts. Another object is to provide a process for preparing the bulky nitrogen compounds and salts thereof. Other objects will become apparent from consideration of the description and the examples.
  • the bulky compounds that contain alkali cleavable alkylamino groups or nitrogen heterocyclic nuclei that are useful in the invention as alkali-release mordants include those represented by the following formula:
  • n, g, and m each represent the same or different integers of from 1 to 2;
  • R represents a lower alkyl (e.g., methyl, ethyl, butyl, etc.), alkoxy (e.g., methoxy, propoxy, butoxy, etc.), aryl (e.g., phenyl, tolyl, ethylphenyl, etc.), aryloxy (e.g., phenoxy, tolyloxy, ethylphenoxy, etc.), aralkyl (e.g., benzyl, phenethyl, etc.), etc.; R and R each represent the same or different members, such as,
  • R represents an alkyl group having from 1 to 20 carbon atoms as described for R and an aryl group (e.g., phenyl, tolyl, octadecylphenyl, methoxyphenyl, dodecoxyphenyl, diphenyl, naphthyl, benzylphenyl, phenoxyphenyl, acetaminophenyl, propion-aminophenyl, laurylaminoph
  • i represents an integer of from 3 to 4;
  • d represents an integer of from 2 to 6;
  • X represents an acid anion (e.g., chloride, bromide, iodide, thiocyanate, sulfamate, perchlorate, methyl sulfate, ethyl sulfate, p-toluenesulfonate, etc.), and when m represents the integer 1, A represents a monofunctional group,
  • R R and R each represent the same or different alkyl group (e.g., methyl, ethyl, decyl, etc.), and R and R taken together represent the nonmetallic atoms required to complete a 6-membered saturated heterocyclic nucleus (e.g., piperidino, morpholino, and N-su-bstituted piperazino (e.g., N-methylpiperazino, N-butylpiperizino, N-phenylpiperizino, etc.), X is as defined previously; R represents hydrogen, or a lower alkyl group (e.g., methyl, ethyl, etc.), each of said A groups having a molecular weight of less than 300; when monofunctional and less than 150 when bifunctional, Z represents the nonmetallic atoms required to complete an imidazoline nucleus; and Z represents the nonmetallic atoms required to complete a nucleus containing a heterocyclic ring having from 5 to 6
  • benzothiazoline nucleus e.g., benzothiazoline, 4-chlorobenzothiazoline, S-chlorobenzothiazoline, -chlorobenzothiazoline, 7-chlorobenzothiazoline, 4-methylbenzothiazoline, S-methylbenzothiazoline, 6-methylbenzothiazoline, 5-bromobenzothiazoline, 6-bromobenzothiazoline, 4-phenylbenzolthiazoline, S-phenylbenzothiazoline, 4-methoxybenzothiazoline, 5-methoxybenzothiazoline, 6-methoxybenzothiazoline, S-iodobenzothiazoline, 6-iodobenzothiazoline, 4-ethoxybenzothiazoline, S-ethoxybenzothiazoline, tetrahydrobenzothiazoline, 5,6-dimethoxybenzothiazoline, 5,6-dioxymethylenebenzothiazoline, 5-hydroxybenzothiazoline, 6-hydroxy
  • a-naphthothiazoline a-naphthothiazoline, ,B-naphthothiazoline, S-methoxy-fi-naphthothiazoline, S-ethoxy-B-naphthothiazoline, 7-methoxy-a-naphthothiazoline, 8-methoXy-a-naphthothiazoline, etc.
  • a thianaphtheno-7,6',4,S-thiazoline nucleus e.g., 4'-methoXythianaphtheno-7',6',4,S-thiazoline, etc.
  • an oxazoline nucleus e.g., 4-methylox-azoline, S-methyloxazoline, 4-phenyloxazoline, 4,5-diphenyloxazoline, 4-ethyloxazoline, 4,5-dimethyloxazoline,
  • a rbenzoxazoline nucleus e.g., benzoxazoline, S-chlorobenzoxazoline, S-methylbenzoxazoline, S-phenylbenzoxazoline, 6-methylbenzoxazoline, 5,6-dimethylbenzoxazoline, 4,6-dimethylbenzoxazoline, S-methoxybenzoxazoline, S-ethoxybenzoxazoline, 6-chlorobenzoxazoline, 6-methoxybenzoxazoline, S-hydroxybenzoxazoline, 6-hydroxybenzoxazoline, etc.) a naphthoxazoline nucleus (e.g., a-n'aphthoxazoline, ,B,5-naphthoxazoline, ,B-naphthoxazoline, etc.-),
  • a naphthoxazoline nucleus e.g., a-n'aphthoxazoline, ,B,5
  • a selenazoline nucleus e.g., 4-methylselenazoline, 4-phenylselenazoline, etc.
  • a benzoselenazoline nucleus e.g., benzoselenazoline, 5-chloroselenazoline, S-methoxyhenzoselenazoline, S-hydroxybenzoselen'azoline, tetrahydrobenzoselenazoline, etc.
  • a naphthoselenazoline nucleus e.g., a-naphthoselenazoline, 5,;3-naphthoselenazoline, fl-naphthoselen azoline, etc.
  • thiazoline nucleus e.g., thiazoline
  • a 1,2,3,4-tetrahydroisoquinoline nucleus e.g., l,2,3,4-tetrahydroisoquinoline, S-methyl-l,2,3,4-tetnahydroisoquinoline, S-methyl-1,2,3,4-tetrahydroisoquinoline, 6-chloro-1,2,3,4-tetrahydroisoquinoline, 6-methoxy-1,2,3,4-tetrahydroisoquinoline, 8-hydroxy-l,2,3,4-tetrahydroisoquinoline, etc.), a 3,3-dialkylindolenine nucleus (e.g., 3,3-dimethylindolenine, 3,3,5-trimethylindolenine, 3,3,7-trimethylindolenine, etc.
  • a 3,3-dialkylindolenine nucleus e.g., 3,3-dimethylindolenine, 3,3,5-trimethylindol
  • a l-substituted imidazoline nucleus e.g., l-alkylimidazoline, 1-alkyl-4-phenylimidazoline, 1-alkyl-4,S-dimethylimidazoline, etc.
  • a l-substituted benzimidazoline nucleus e.g., l-alkylbenzimidazoline, 1-aryl-5,6-dichlorobenzimidazoline, etc.
  • a l-substituted naphthimidazoline nucleus e.g., 1-alkyl-u-naphthimidazoline, 1-aryl-fi-naphthimidazoline, 1-alkyl-5-methoxy-wnaphthimidazoline, etc.
  • a 1,2,4-thiadiazoline nucleus a lor 4-alkyl-1,2,4-triazoline nucleus (e.g.
  • tetrazoline nucleus e.g. tetrazoline, S-methyl-1,2,3,4-tetrazoline, 5-phenyl-1,2,3,4-tetrazoline, etc. and the like nuclei.
  • the components of Formula I above are so chosen as to give compounds having molecular weights in each instance of at least 150 for compounds derived from di-amines and 300 for compounds derived from monofunctional amines.
  • the compounds containing the -NR R groups are used in the form of their salts (e.g., the hydrochloride, the acetate, etc.) or in their quaternized forms, i.e., containing the group 5 -NR X ⁇ R1 wherein X, R R and R are as previously defined.
  • R R R R R and X are as defined previously and R represents the hydrogen atom, a straight or branched chain al-kyl group of from 1 to 22 carbon atoms (e.g., methyl, ethyl, propyl, isopropyl, butyl, hexyl, dodecyl, octadecyl, etc.), an aryl group (e.g., phenyl, tolyl, naphthyl, etc.), an aralkyl group (e.g., benzyl, phenethyl, etc.), an alkoxy group (e.g., methoxy, ethoxy, butoxy, etc.) an aryloxy group (e.g., phenoxy, tolyloxy, naphthoxy, etc.), an alkoxyalkyl group (e.g., methoxymethyl, ethoxybutyl, isopropoxybutyl,
  • R is as defined previously and an amine (or amine salt) having one of the formulas;
  • R R R X and a are as defined previously or XL Z R;HdI I-R in which R and Z have been defined previously and R represents an alkyl group having from 1 to 4 carbon atoms.
  • mordants of Formula I in which m is 1 are produced advantageously by reacting compounds of Formulas IV, V, and VI or XI in mole ratios of about 1:1:1 respectively, while the compounds in which m is 2 are produced advantageously by reacting compounds of Formulas IV, V, and VII and VIII or IX or X in mole ratios of about 2:2:1 respectively.
  • the immediate reactions are advantageously carried out in a solvent such as glacial acetic acid and preferably at an elevated tmeperature, for example on a steam bath for several hours, the product then being precipitated by adding a nonsolvent (e.g., acetone), filtered out and recrystallized, for example, from absolute ethyl alcoholethyl acetate mixture.
  • a nonsolvent e.g., acetone
  • recrystallized for example, from absolute ethyl alcoholethyl acetate mixture.
  • Illustrative aldehydes used to advantage include formaldehyde, paraformaldehyde, acetaldchyde, benzaldehyde, etc.
  • Any monofunctional primary or secondary amine having a molecular weight of less than 300 or a bifunctional primary or secondary amine having a molecular weight of less than 150 can be used to advantage.
  • Typical monofunctional amines includes the following:
  • Typical bifunctional amines include the following:
  • Mordant No. Name 1 3 lauroylamino 1 (N,N-dimcthyl-3- amino) propiophenone hydrochloride.
  • the above-defined mordants of the invention function as alkali-release mordants in photographic layers.
  • they decompose to split or cleave the basic nitrogen fragment off of the bulky residue, and to lose their ability to act as mordants with release and subsequent removal of the mordanted dye from the system.
  • a major advantage of the above alkalirelease 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.
  • R R R R and X are as previously defined.
  • the invention is further illustrated by the following examples describing the preparation and use of the mordanting compounds of the invention in photographic layers and elements.
  • Example 1.3-lauroylamino-1-(N,N-dimethyl-3- amino)propiophenone hydrochloride A mixture of 10 g. 3-1aurolya1ninoacetophenone (0.031 mole), 3.6 g. dimethylamine hydrochloride (0.044 mole), 2.5 g. paraformaldehyde (0.028 mole) in ml. glacial acetic acid was warmed on a steam bath for 3 hours. The dark red reaction mixture was reduced in volume under reduced pressure. Acetone was added to the concentrated solution. The resulting precipitate was collected and recrystallized from absolute ethanol-ethyl acetate, M.P. 1624.5 C.
  • the above compound 3-lauroylamino-1-(N,N-dimethyl- 3-amino)propiophenone hydrochloride is an alkali cleavable Mannich base which can be decomposed in alkali splitting the basic nitrogen fragement off of the bulky residue.
  • This compound at a ratio of parts by weight to 1 part by weight of dye, mordanted the dye bis [3- methyLl-p-sulfophenyl 2 pyrazolin-5-one-(4)] pentamethineoxonol, in gelatin at a pH of 5.0, with no bleeding upon washing in water.
  • the mordanted dye was partially bleached upon treatment of the coated gelatin layer (on a cellulose acetate film support) with a photographic developer having the composition:
  • the bleaching was increased when the alkalinity of the developer was increased by the addition of sodium hydroxide.
  • the residual yellow color was discharged by subsequent acidification of the gelatin layer. This was 10 mined, but none of the above samples bleached under these conditions.
  • Thiosulfate retention values were determined by the Ross-Crabtree Method on unexposed film coatings, processed in a commercial Recordak processing machine.
  • EXAMPLE 2 Similar results are obtained by substituting for mordant No. 1 in Example 1 any of the specific illustrative mordants described previously herein. In each instance the dye being mordanted is held securely in its coated layer but upon photographic processing in the alkaline processing solutions the dye is completely released from the layer. The fragments into which the mordant is cleaved by alkali are not capable of and do not retain any dye or any thiosulfate ion in the processed photographic element.
  • the other odd-numbered mordants used to illustrate my invention are advantageously prepared by the Mannich condensation by processes Well known in .the art.
  • Table 1 lists the ketone, aldehyde and amine salt used to make the mordants. Unless otherwise indicated, approximately equimolar amounts are used.
  • the even-numbered mordants are made from the preceding odd-numbered mordants by treating it with methyl iodide.
  • mordants of my invention are the position: following: i thlosulfate MO -dam; N NaIne si deslccated 48 33 6-(N,Ndimethylaminornethyl)-2-phenyl- Aceilc s 2 i 7 5 r cyclohexanone hydrochloride, Bone acid, crystals 00 34 6-(N,N-diethylarninomethyl)-2-tolyl-cyc1o- Potasslum 211ml t '0 hexanone hydrochloride.
  • WateF-T0 ma 6 11 35 N,N-dibutylaminomethylcyclopentanone Result:Mordanted well. Bleached effectively in the hydrochlor de.
  • Example 1 The above results for Example 1 were made for hand 55 ethyl)hydrochloride.
  • the bleed test consisted of immersinga portion of the hand coating in stagnant, distilled water at 75 F. for 2 minutes and inspecting for signs of dye bleeding out of the gel layer. If no bleeding was detected, the immersion was repeated for another 2 minute interval. Bleachability was determined by immersing a portion of the hand coating in the developer for 2 minutes and observing the loss in color. Bleachability in the fixing bath was also deter-
  • the photographic elements prepared with the abovedescribed 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 light-sensitive 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 emulsionlayer.
  • the mordant containing light-screening and antihalation layers are customarily prepared by coating on the support or photographic elements 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.
  • the colloidal binder material For most purposes, it is also desirable to add agents to harden the colloidal binder material so that the light-screening layer will remain intact in the photographic element during and following the processing operations.
  • 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.
  • the proportions of mordant, dye, colloidal binder, hardener and coating aid may be varied over wide ranges and will depend upon the specific requirement of the photographic element being produced. The methods used to determine the optimum compositions are well known in the art and require no further elucidation here.
  • 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 above-mentioned amphoteric copolymers are made by polymerizing the monomer having the 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%, and preferably from -15%, 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 allylamine 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 my invention include any filter dye that has one or more acidic group substituents such as sulfo or carboxyl groups, including 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 1-carboxyalkyl-3-hydrocarbon substituted hexahydro-2,4,6-trioxo-5-pyrimidine nucleus
  • n in each case is an integer of from 1 to 3
  • each R represents a carboxy- -alkyl 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 alk-oxy substituted phenyl group
  • X is hydrogen or an alkyl group of from 1 to 4 carbon atoms, such that no more than one X" is an alkyl group.
  • Suitable acid dyes include the benzoxazole-pyrazolone merocyanine dyes described in copending application of Jones et al. U.S. Ser. No. 167,666, filed Jan. 22, 1962, now Patent No. 3,282,699, having the formula:
  • R 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 on the benzene ring as well as one or more of
  • 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, for example, the yellow dyes mentioned in Mader et al. U.S. Patent 3,016,306, issued Jan. 9, 1962, columns 5 and 6.
  • Typical light-filtering dyes include, for example,
  • typical ultraviolet absorbing dyes include the 2,5-bis(substituted sulfophenyl)thiazolo[5,4-d]thiazole disodium salts of Sawdey U .S. Ser. 183,417 filed Mar. 29, 1962, such as 2,5 -bis o-methoxy-x-sulfophenyl thiazolo ,4-d] thiazole disodium salt,
  • tartrazine and the like filter dyes.
  • Hardening materials that may be used to advantage include such hardening agents as formaldehyde; a halogensubstituted 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-diphenylbicyclo (2,2,2)-7-octene'-2,3,5, 6-tetra-carboxylic dianhydride, or a dicarboxylic or a disulfonic acid chloride such as terephthaloyl chloride or naphthalene-1,5-disulfonyl chloride as described in Allen and Carroll U.S.
  • hardening agents as formaldehyde; a halogensubstituted 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-dipheny
  • the photognaphic element utilizing my 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.
  • FIG. 1 shows light-screening layer 10 comprising gelatin, an acid substituted filter dye and the mordant of Example 1 coated over a light-sensitive silver halid emulsion layer 11 which is coated on support 12.
  • FIG. 2 shows antihalation layer 15 comprising gelatin, an acid substituted dye and the mordant of Example 1,
  • 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 mordant of Example 1 coated over layer 19, and a blue-sensitive silver halide emulsion layer 17 coated over layer 18.
  • 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 trapsfer blanks of improved properties.
  • a photographic element comprising a support material having thereon a hydrophilic colloid layer containing at least one mordant represented by the formula:
  • R represents a member selected from the class consisting of an alkyl group, an aryl group and when taken together with the R group represents the said divalent alkylene group, such that when R and R are taken together to form said divalent alkylene group, n and g each represent the integer 1;
  • R represents a member selected from the class consisting of hydrogen, an alkyl group and an aryl group;
  • R represents a member selected from the class consisting of hydrogen, an alkyl group and an aryl group; when m represents the integer 2
  • A represents a bifunctional group having a molecular weight less than in which each of the said functional groups is a substituted nitrogen atom having a valence with an odd number of from 3 to 5 with none of the said substituents attached to nitrogen being hydrogen, and when the nitrogen atoms have a valence of 5, one of said substituents on each of said nitrogen atoms is an acid anion, and when m represents the integer 1, A represents a substituted nitrogen having
  • R R and R each represents an alkyl group, and together R and R represent the nonmetallic atoms required to complete a group selected from the class consisting of piperidine, N-substituted piperazine, and morpholine;
  • R represents a member selected from the group consisting of hydrogen, and a lower alkyl group;
  • X represents an acid anion and Z represents the nonmetallic atoms required to complete a heterocyclic nucleus having from 5 to 6 members in the ring selected from the class consisting of a thiazoline nucleus, a benzothiazoline nucleus, a naphthothiazoline nucleus, a thianaphtheno-7,6',4,S-thiazoline nucleus, an oxazoline nucleus, a benzoxazoline nucleus, a naphthoxazoline nucleus, a selenazoline nucleus, a benzoselenazoline nucleus, a naphthose
  • a light-sensitive photographic element comprising a support material having thereon a hydrophilic colloid layer container at least one substantially nonditfusible salt of a water-soluble acid dye with a compound represented by the formula:
  • R and R each represents an alkyl group, R and R taken together represent the nonmetallic atoms required to complete a group selected from the class consisting of piperidine, N-substituted piperazine and morpholine; and R represents a member selected from the class consisting of the hydrogen atom, an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an alkoxyalkyl group, and an acylamino group; said compound having a molecular weight of at least 300, said element containing silver halide.
  • a light-sensitive photographic element comprising a support material having thereon a hydrophilic colloid layer containing at least one substantially nonditfusible salt of a water-soluble acid dye with a compound represented by the formula:
  • R R and R each represents an alkyl group, R and R taken together represent the nonmetallic atoms required to complete a group selected from the class consisting of piperidine, N-substituted piperazine and morpholine;
  • R represents a member selected from the class consisting of the hydrogen atom, an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an alkoxyalkyl group, and an acylamino group;
  • X represents an acid anion; said compound having a molecular weight of at least 300, said element containing silver halide.
  • a light-sensitive photographic element comprising a support material having thereon a hydrophilic colloid layer containing at least one substantially nondiffusible salt of a water-soluble acid dye with 3-lauroylaminol- (N,N-dimethyl-3-amino propiophenone hydrochloride, said element containing silver halide.
  • a light-sensitive photographic element comprising a support material having thereon a hydrophilic colloid layer containing at least one substantially nondifiusible salt of a water-soluble acid dye with 3-dodecylphenylcarbamylcarbonylethyl N,N dimethylamine hydrochloride, said element containing silver halide.
  • a light-sensitive photographic element comprising a support material having thereon a hydrophilic colloid layer containing at least one substantially nondilfusible salt of a water-soluble acid dye with 3-laurylbenzoylethyl- N-methyl-N-morpholinium iodide, said element containing silver halide.
  • a light-sensitive photographic element comprising a support material having thereon a hydrophilic colloid layer containing at least one substantially nondiffusible salt of a water-soluble acid dye with 1,4-bis(3-laurylbenzoylethyl)-N,N-dimethylpiperazinium diiodide, said element containing silver halide.
  • a light-sensitive photographic element comprising a support material having thereon a hydrophilic colloid layer containing at least one substantially nondiffusible salt of a water-soluble acid dye with 6-(N,N-dimethylaminomethyl)-2-laury1cyclohexane hydrochloride, said element containing silver halide.
  • a light-sensitive photographic element comprising a support material having thereon a hydrophilic colloid layer containing at least one substantially nondifrusible salt of a watersoluble acid dye with N-methyl-N,N-bis (3-laurylbenzoylethyl)amine hydrochloride, said element containing silver halide.
  • a light-sensitive photographic element comprising a support material having thereon a hydrophilic colloid layer containing at least'one substantially nondifiusible salt of a Water-soluble acid dye with 1,5-bis(3-laurylbenzoylethyl) N,N'-dimethylpentamethylenediamine dihydrochloride, said element containing silver halide.
  • a light-sensitive photographic element comprising a support material having thereon a 'hydrophilic colloid layer containing at least one substantially nondilfusible salt of a water-soluble acid dye with l,3-di(3-laurylbenzoylethyl)benzimidazolinium diiodide, said element containing silver halide.
  • a light-sensitive photographic element comprising a support material having thereon a hydrophilic colloid layer containing at least one substantially nondiffusible salt of a water-soluble acid dye with phytylethyl-N,N,N- trimethyl ammonium iodide, said element containing silver halide.
  • An element comprising a support material having thereon a hydrophilic colloid layer containing at least one salt of an acid dye and a mordant represented by the formula:
  • R represents an integer of from 3 to 4;
  • m represents an integer of from 1 to 2;
  • R represents a member selected from the class consisting of a lower alkyl group, a lower alkoxy group, an aryl group, an aryloxy group and an aralkyl group;
  • R represents a member selected from the class consisting of hydrogen, an alkyl group, an aryl group, and when taken together with the R group represents a divalent alkylene group having the formula:
  • R represents a member selected from the class consisting of an alkyl group, an aryl group and when taken together with the R group represents the said divalent alkylene group, such that when R and R are taken together to form said divalent alkylene group, n and g each represent the integer 1;
  • R represents a member selected from the class consisting of hydrogen, an alkyl group and an aryl group;
  • R represents a member selected from the class consisting of hydrogen, an alkyl group and an aryl group; when m represents the integer 2,
  • A represents a bifunctional group having a molecular weight less than in which each of said functional groups is a substituted nitrogen atom having a valence with an odd number of from 3 to 5 with none of the said substituents attached to nitrogen being hydrogen, and when the nitrogen atoms have a valence of 5, one of said substituents o neach of said nitrogen atoms is an acid anion, and when

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  • Structural Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US479719A 1965-08-16 1965-08-16 Mordants for bleachable filter layers Expired - Lifetime US3425834A (en)

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US47971965A 1965-08-16 1965-08-16

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US (1) US3425834A (enrdf_load_stackoverflow)
BE (1) BE685241A (enrdf_load_stackoverflow)
CH (1) CH466701A (enrdf_load_stackoverflow)
GB (1) GB1161131A (enrdf_load_stackoverflow)

Cited By (1)

* 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

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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 (1)

* 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

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BE685241A (enrdf_load_stackoverflow) 1967-01-16
GB1161131A (en) 1969-08-13

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