US2839401A - Photographic silver halide emulsions containing copolymeric mordants - Google Patents

Photographic silver halide emulsions containing copolymeric mordants Download PDF

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Publication number
US2839401A
US2839401A US478544A US47854454A US2839401A US 2839401 A US2839401 A US 2839401A US 478544 A US478544 A US 478544A US 47854454 A US47854454 A US 47854454A US 2839401 A US2839401 A US 2839401A
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United States
Prior art keywords
tertiary
silver halide
quaternary
photographic
dye
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Expired - Lifetime
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US478544A
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English (en)
Inventor
Gray Russell Houston
Webers Vincent Joseph
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EIDP Inc
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EI Du Pont de Nemours and Co
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Publication date
Priority to BE543031D priority Critical patent/BE543031A/xx
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to US478544A priority patent/US2839401A/en
Priority to GB32233/55A priority patent/GB786592A/en
Priority to DEP15327A priority patent/DE1000688B/de
Priority to FR1148470D priority patent/FR1148470A/fr
Priority to US574593A priority patent/US2892822A/en
Application granted granted Critical
Publication of US2839401A publication Critical patent/US2839401A/en
Anticipated expiration legal-status Critical
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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
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/22—Subtractive cinematographic processes; Materials therefor; Preparing or processing such materials
    • G03C7/25—Dye-imbibition processes; Materials therefor; Preparing or processing such materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F28/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a bond to sulfur or by a heterocyclic ring containing sulfur
    • 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
    • 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
    • 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
    • Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
    • Y10S526/923—Ethylenic monomers containing at least one salt group

Definitions

  • This invention relates to photography and more particularly to photographic silver halide emulsions containing copolymeric mordants for acid dyes. Still more particularly, it relates to photographic silver halide emuland quaternary ammonium groups and which are effective mordants for acid dyes. By tertiary amino groups,
  • Yet another object is to provide copolyineric dye mordants which are non-diffusing in waterpermeable colloid layers and have no deleterious action on light-sensitive silver halides. Still other objects will tion.
  • polymeric substituted or unsubstituted acrylic acid esters of amino alcohols having tertiary and quarternary salt groups in the proportion of 35% to 75% and preferably 35% to 65% of the former to 65% to and preferably 65% to of the latter can be prepared by polymerizing, preferably under an inert atmosphere, e. g., of nitrogen, a mixture of aqueous solutions of tertiary and quaternary monomeric, subs'titutedor unsubstituted acrylic acid esters by the aid of anfaddition polymerization initiator, e. g., ammonium persillfate.
  • an inert atmosphere e. g., of nitrogen
  • the tertiary amine salt and the quaternary salt are employed in the same molecular proportions as sc't forth above for the component parts of the polymer.
  • the compounds provided by and used in accordance it h this invention contain intralinear units of the general formulae:
  • R and R are hydrogen or alkyl groups of 1 to 2 carbon atoms, e. g., methyl and ethyl, R and R are alkyl radicals of 1 to 6 carbon atoms or taken together form a divalent hydrocarbon radical of 4 to 6 carbon atoms,
  • R is an alkyl radical of 1 to 18 carbon atoms, R and R are alkyl radicals of 1 to 6 carbon atoms or together form a divalent hydrocarbon radical of 4 to 6 carbon atoms, In and n are the number of monomer units in the copolymer which has a molecular weight of at least 2000; a and b are the integers 2, 3 or 4; Y is a non-photographically active anion and Z is a non-photographically active anion, preferably of an oxygen-containing sulfur acid as described below. Units m are present in the amount of 25 to 65 mol per cent and units 11 in the amount of 75 to 35 mol per cent.
  • Suitable alkyl radicals for R R R R R and R of the above formulae include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, decyl, dcdecyl, tetradecyl and octadecyl. in the case wherein R and R together and also R and R together form cyclic radicals with the nitrogen atoms, such radicals include pyrrolidine, piperidine and mo-rpholine.
  • peroxygen compounds e. g., ammonium persulfate, benzoyl peroxide and hydrogen peroxide
  • azo catalysts e. g., a x azo-bisisobutyramidine hydrochloride.
  • reaction in the event the rate of polymerization is too rapid, the reaction can be slowed or controlled by the addition of an inhibitor, e. g., tertiary-butyl catechol or oxygen.
  • an inhibitor e. g., tertiary-butyl catechol or oxygen.
  • the anion of both the tertiary and quaternary salt groups is an anion of an oxygen-containing strong sulfur acid of ionization constant greater than l l0
  • suitable such acids are sulfuric, alkariesulfonic acids of 1 to 12 carbon atoms, e. g., methanesulfonic, ethanesulfonic, decanesulfonic acid and dodecanesulfonic acid; arylsulfonic acids, e. g., benzenesulfonic and p-toluenesulfonic acid; and cycloalkanesulfonic acids, e.
  • alkylsulfuric acids wherein the alkyl group contains 1 to 6 carbon atoms, e. g., methylsulfuric acid.
  • suitable anions include phosphate and perchlorate.
  • Suitable unsaturated esters of amino alcohols for the preparation of the tertiary and quaternary salts are described in Graves U. S. Patent 2,138,763. made in accordance with Examples 1 through 11, or from suitable amino alcohols listed on page 5 of said patent.
  • the preferred compounds for the preparation of the tertiary and quaternary salts are dimethylaminoethyl methacrylate and diethylaminoethyl methacrylate.
  • the quaternary salts of these unsaturated esters of amino alcohols can be made by quaternization of these esters with alkyl esters of the strong sulfur acids listed above at 0 C. to C. or higher as described in Barney U. S. Patent 2,677,699 of May 4, 1954.
  • the tertiary salts can be made by the neutralization of the free base with suitable acids such as are described above.
  • the improved photographic emulsions and emulsion layers of this invention can be made by simply mixing the copolymers having tertiary and quaternary salt groups in the proportion of 35% to of the former to 65% to 25% of the latter with an aqueous dispersion or emulsion of light-sensitive silver halide in a Water-permeable colloid, which may contain the usual emulsion adjuvants, e. g., sensitizing dyes, hardeners, etc. prior to coating onto a suitable support or layer of a photographic element.
  • an amount of copolymer corresponding to 0.03 to 0.5 mol of nitrogen-containing monomers is used per 1.5 mols of silver halide.
  • the resulting prod- They can be 7 ucts have excellent mordanting properties with respect to acid dyes.
  • novel tertiary/quaternary salt copolymeric mordants described above are non-diffusing in gelatin, polyvinyl alcohol and similar water-permeable colloid layers and are superior in many respects to the corresponding compounds containing 80% to 100% quaternary salt groups.
  • the latter while effective mordants, result in emulsions of excessive fog characteristics.
  • the corresponding compounds containing only tertiary salt groups in general, seriously lower the speed and gamma of the resultant product.
  • Applicants have found that the presence of both tertiary and quaternary salt groups in the same polymer molecule in the above ratios produce emulsions of satisfactory photographic quality that have an excellent mordanting action for acid dyes. Mixtures of tertiary and quaternary homopolymers containing the equivalent amount of each group do not give the same results and result in intolerable fog or other undesirable photographic characteristics.
  • the water-permeable colloids used in the emulsions may be of any of the usual colloids used by photographic manufacturers.
  • the colloid may be gelatin, agaragar, albumin, zein, collodion, polyvinyl alcohol, partially hydrolyzed polyvinyl acetate and hydrophilic copolymers thereof with ethylenically unsaturated monomers such as ethylene, vinyl chloride, etc.; polyvinyl acetals, e. g., the acetal of polyvinyl alcohol with acetaldehyde or benzaldehyde; or water-soluble or hydrophilic cellulose derivatives.
  • Suitable hydrophilic or waterpermeable colloids of the above types are described in U. S. Patents 2,110,491, 2,211,323, 2,276,322, 2,276,323, 2286,215 and 2,397,866.
  • PROCEDURE A TERTIARY MONOMER
  • PROCEDURE B QUATERNARY MONOMER
  • Example I A copolymer containing 35 mol percent quaternary and 65 mol percent tertiary salt was prepared by admixing 35 ml. of the solution of methyldiethylmethacryloxyethyl-ammonium methyl sulfate monomer of Procedure B above and 65 ml. of the solution of diethylaminoethylmethacrylate methylsulfate of Procedure A and 0.1 gram of ammonium persulfate and the mixture was heated to 5055 C. under an atmosphere of nitrogen while stirring until polymerization was approximately complete (i. e., between 1 and 1.5 hours). The pH was kept between 6.5 to 7.5 by the addition of aqueous NaOH solution (5%).
  • Sodium dimethyldithiocarbamate was added from 2% aqueous solution in the proportion of 15 ml. per liter of the polymerization mixture, in order to prevent further polymerization.
  • the solution of copolymer of the above composition was allowed to cool and was diluted with water to 0.129 normal and stored at room temperature until used in a photographic emulsion.
  • Example 11 The procedure of Example I was repeated except 55 ml. of the tertiary salt solution and 45 ml. of the quaternary salt solution were used to make a copolymer containing corresponding percentages of the respective salt groups.
  • Example 111 The procedure of Example I was repeated except-that 35 ml. of the tertiary salt solution and 65 ml. of the quaternary salt solution were used to make a copolymer containing corresponding percentages of the respective salt groups.
  • Example IV A portion of each solution prepared in accordance with Examples I, II and III corresponding to 0.161 mols of monomer (approximately 50 grams of polymer) for each 1.5 mols of silver halide was added respectively to separate portions of a molten light-sensitive silver bromoiodide gelatin positive type emulsion of 0.6 mol percent silver iodide containing 1.5 mols of silver halide and 273 grams of gelatin. Similar solutions of mixtures of the same proportions of homopolymers containing the same tertiary salt groups only and homopolymers containing the same quaternary salt groups only and made by the polymerization procedures above, were added in like amount to emulsions in the manner described in the preceding sentence.
  • Pontacyl Carmine 6B Extra Concentrated (Colour index No. 57) grams 1.56 1% acetic acid to make 1.0 liter.
  • the dyed strips were rinsed in 1% acetic acid solution for 1 minute and cut into halves. One half was dried and the other half was washed in running water at 68 F. for 1 hour, then dried. The optical density of each sample at 540 mu was detennined and the dye retained, calculated as follows:
  • Example V Copolymers containing both tertiary and quaternary salt groups and mixtures of homopolymers containing tertiary and quaternary salt groups only as described in Example I were used to prepare another set of coatings by the procedure described in Example IV.
  • Example VI Copolymers of the kind described in Example I but containing quaternary salt groups and tertiary salt groups in the amounts given in the following table were made as described in that example. The copolymers were used to make emulsion coatings which were made, exposed, developed, fixed and tested for dye mordanting properties as described in Example IV with the following results:
  • actinic light was excluded during the preparation of the photographic emulsions and emulsion layers until after development and fixing.
  • copolyrners containing both tertiary and quaternary salt groups described in the foregoing examples there can be made and used in photographic emulsions and emulsion layers other such copolyrners as shown under the general formula given above. Mixtures of two or more of such copolymers, each containing tertiary and quaternary salt groups can be used. The polymerizations can be carried out at temperatures from 40 C. to 100 C. or more and for a period of /2 to 3 or more hours.
  • the invention is not limited to the use of the gelatin coated cellulose triacetate film base since the water-permeable silver halide emulsion layers containing the copolymeric tertiary/quaternary salts can be coated on various supports, e. g., baryta coated paper or cardboard or water-proofed or transparentized paper or a film.
  • the film sup- 7 port may be a hydrophobic superp'olymer; e. g., a polyamide, a polyester such as polyethylene terephthalate, a polyvinyl acetal, polystyrene, polyvinyl chloride and a poly(vinyl chloride co vinyl acetate).
  • the coated film base described in Alles et *al. U. S. Patent No. 2,627,088 is especially useful as a base sheet.
  • An advantage of the invention is that it provides a new class of copolymeric salts which have utility in various arts. Since they are quite water-soluble, they can be applied from aqueous solutions. Thus the solutions can be used for antistatic coatings on photographic film bases or cellophane, emulsifying agents for wax, oil or insecticide dispersions, surface modifiers for glass or silica, dye fixatives for acid dyes or textile modifiers.
  • the copolymeric salts are especially useful as mordants for acid dyes in photographic processes.
  • Premordanted light-sensitive photographic films containing the novel polymeric salts in light-sensitive water-permeable colloid silver halide emulsion layers are useful, for example, in preparing dye imbibition or dye transfer prints by transfer from a hardened gelatin matrix.
  • the premordanted films may be exposed and processed before dye transfer so that the film will bear records of silver, e. g., an optical sound track.
  • a further advantage of the invention is that the copolymeric tertiary/ quaternary salts do not fog silver halide emulsion layers and can be incorporated directly therein.
  • Other monomeric or homopolymeric acid dye mordants described in the prior art have had to be used in separate contiguous coatings on silver halide layers due to their undesirable photographic action, thus making these films more costly to manufacture.
  • the use of the mordant in the silver halide layer produces dye images of increased sharpness.
  • the premordanted films so produced are easier to process. Still other advantages will be apparent from the above.
  • a photographic silver halide emulsion in a waterpermeable colloid containing in mordanting amounts a linear addition copolymer consisting essentially of intralinear quaternary ammonium and tertiary amine salt units wherein R and R are members taken from the group consisting of hydrogen and alkyl groups of 1 to 2 carbon atoms, R and R when separate are alkyl radicals of 1 to 6 carbon atoms and whenjoined form a cyclic radical comprising 4 to 6 carbon atoms, R is an alkyl radical of l to 18 carbon atoms, R and R when separate are alkyl radicals of 1 to 6 carbon atoms and when joined together form a cyclic radical comprising 4 to 6 carbon atoms, a and b are positive integers of 2 to 4 inclusive, m and n are the number of monomer units in the copolymer and Y and Z- are non-photographically active anions; said monomer units m and n being present in the mol percent ratio of
  • A'photographic silver halide emulsion in a water permeable colloid containing in mordanting amounts a copolymeric dimethylaminoethyl methacrylate having tertiary amine salt and quaternary ammonium salt groups, said salt groups being present in the proportion of 35 to 75 mol percent of the former to 65 to 25 mol percent of the latter, the salt forming anion being of an oxygencontaining strong sulfur acid of ionization constant greater than 10 3.
  • An emulsion as set anion is methylsulfate.

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  • Chemical & Material Sciences (AREA)
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  • General Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
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  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
US478544A 1954-12-29 1954-12-29 Photographic silver halide emulsions containing copolymeric mordants Expired - Lifetime US2839401A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
BE543031D BE543031A (en, 2012) 1954-12-29
US478544A US2839401A (en) 1954-12-29 1954-12-29 Photographic silver halide emulsions containing copolymeric mordants
GB32233/55A GB786592A (en) 1954-12-29 1955-11-10 Polymeric esters and products containing them
DEP15327A DE1000688B (de) 1954-12-29 1955-12-15 Wasserdurchlaessige photographische Halogensilber-Emulsion
FR1148470D FR1148470A (fr) 1954-12-29 1955-12-15 Esters polymères et produits contenant ces esters polymères
US574593A US2892822A (en) 1954-12-29 1956-03-29 Acrylate copolymers containing quaternary ammonium and tertiary amine salt units

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US478544A US2839401A (en) 1954-12-29 1954-12-29 Photographic silver halide emulsions containing copolymeric mordants

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BE (1) BE543031A (en, 2012)
DE (1) DE1000688B (en, 2012)
FR (1) FR1148470A (en, 2012)
GB (1) GB786592A (en, 2012)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3075841A (en) * 1956-06-19 1963-01-29 Du Pont Mordant treating process and elements containing same
US3316087A (en) * 1959-10-31 1967-04-25 Azoplate Corp Photoconductor coatings for electrophotography
US3411912A (en) * 1965-04-21 1968-11-19 Eastman Kodak Co Novel polymers and their use in photographic applications
US3455693A (en) * 1965-08-16 1969-07-15 Eastman Kodak Co Mordants for use in dyed filter layers
US3488706A (en) * 1968-03-01 1970-01-06 Eastman Kodak Co Novel polymers containing quaternary ammonium groups
US3549605A (en) * 1965-04-21 1970-12-22 Eastman Kodak Co Novel polymers and their use in photographic applications
US3816129A (en) * 1973-01-02 1974-06-11 Polaroid Corp Synthetic silver halide emulsion binder
USB320452I5 (en, 2012) * 1973-01-02 1975-01-28
US3962527A (en) * 1973-03-09 1976-06-08 Eastman Kodak Company Novel polymers and photographic elements containing same
FR2406230A1 (fr) * 1977-10-11 1979-05-11 Eastman Kodak Co Composition photosensible et produi
US4299898A (en) * 1979-05-03 1981-11-10 Xerox Corporation Positively charged toners containing quaternary ammonium salts attached to acrylate polymers
EP0209118A2 (en) 1985-07-17 1987-01-21 Konica Corporation Silver halide photographic material
EP0256537A2 (en) 1986-08-15 1988-02-24 Fuji Photo Film Co., Ltd. Color print and a method for producing the same
US20140342290A1 (en) * 2013-05-17 2014-11-20 Az Electronic Materials (Luxembourg) S.A.R.L. Composition comprising a polymeric thermal acid generator and processes thereof

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB912754A (en) * 1959-08-19 1962-12-12 Polaroid Corp Photographic colour transfer process and product
CN113980196B (zh) * 2021-10-18 2023-09-15 佳化化学科技发展（上海）有限公司 一种聚羧酸聚合物及其制备方法和应用

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2461023A (en) * 1944-10-25 1949-02-08 Gen Aniline & Film Corp Photographic silver halide emulsions
US2495918A (en) * 1948-08-28 1950-01-31 Du Pont Poly-n-vinyl lactam photographic silver halide emulsions
US2539706A (en) * 1946-04-19 1951-01-30 Us Rubber Co Copolymer of dimethallyl ether and an alkyl acrylate
US2566250A (en) * 1948-11-20 1951-08-28 Eastman Kodak Co New polymers containing lactam units in the polymer chain
US2600446A (en) * 1949-07-15 1952-06-17 Rohm & Haas Copolymers of methacrylates and allyl esters
US2678884A (en) * 1949-11-18 1954-05-18 Du Pont Photographic silver halide emulsions of synthetic polymers

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2461023A (en) * 1944-10-25 1949-02-08 Gen Aniline & Film Corp Photographic silver halide emulsions
US2539706A (en) * 1946-04-19 1951-01-30 Us Rubber Co Copolymer of dimethallyl ether and an alkyl acrylate
US2495918A (en) * 1948-08-28 1950-01-31 Du Pont Poly-n-vinyl lactam photographic silver halide emulsions
US2566250A (en) * 1948-11-20 1951-08-28 Eastman Kodak Co New polymers containing lactam units in the polymer chain
US2600446A (en) * 1949-07-15 1952-06-17 Rohm & Haas Copolymers of methacrylates and allyl esters
US2678884A (en) * 1949-11-18 1954-05-18 Du Pont Photographic silver halide emulsions of synthetic polymers

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3075841A (en) * 1956-06-19 1963-01-29 Du Pont Mordant treating process and elements containing same
US3316087A (en) * 1959-10-31 1967-04-25 Azoplate Corp Photoconductor coatings for electrophotography
US3411912A (en) * 1965-04-21 1968-11-19 Eastman Kodak Co Novel polymers and their use in photographic applications
US3549605A (en) * 1965-04-21 1970-12-22 Eastman Kodak Co Novel polymers and their use in photographic applications
US3455693A (en) * 1965-08-16 1969-07-15 Eastman Kodak Co Mordants for use in dyed filter layers
US3488706A (en) * 1968-03-01 1970-01-06 Eastman Kodak Co Novel polymers containing quaternary ammonium groups
US3925083A (en) * 1973-01-02 1975-12-09 Polaroid Corp Synthetic silver halide emulsion binder
USB320452I5 (en, 2012) * 1973-01-02 1975-01-28
US3816129A (en) * 1973-01-02 1974-06-11 Polaroid Corp Synthetic silver halide emulsion binder
US3962527A (en) * 1973-03-09 1976-06-08 Eastman Kodak Company Novel polymers and photographic elements containing same
FR2406230A1 (fr) * 1977-10-11 1979-05-11 Eastman Kodak Co Composition photosensible et produi
US4299898A (en) * 1979-05-03 1981-11-10 Xerox Corporation Positively charged toners containing quaternary ammonium salts attached to acrylate polymers
EP0209118A2 (en) 1985-07-17 1987-01-21 Konica Corporation Silver halide photographic material
EP0256537A2 (en) 1986-08-15 1988-02-24 Fuji Photo Film Co., Ltd. Color print and a method for producing the same
US20140342290A1 (en) * 2013-05-17 2014-11-20 Az Electronic Materials (Luxembourg) S.A.R.L. Composition comprising a polymeric thermal acid generator and processes thereof
CN105164172A (zh) * 2013-05-17 2015-12-16 Az电子材料卢森堡有限公司 包含聚合热酸发生剂的组合物及其方法
US9291909B2 (en) * 2013-05-17 2016-03-22 Az Electronic Materials (Luxembourg) S.A.R.L. Composition comprising a polymeric thermal acid generator and processes thereof
CN105164172B (zh) * 2013-05-17 2018-07-10 Az电子材料卢森堡有限公司 包含聚合热酸发生剂的组合物及其方法

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GB786592A (en) 1957-11-20
DE1000688B (de) 1957-01-10
BE543031A (en, 2012)
FR1148470A (fr) 1957-12-10

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