US3253921A - Novel photographic elements protected against ultraviolet radiation - Google Patents

Novel photographic elements protected against ultraviolet radiation Download PDF

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US3253921A
US3253921A US144228A US14422861A US3253921A US 3253921 A US3253921 A US 3253921A US 144228 A US144228 A US 144228A US 14422861 A US14422861 A US 14422861A US 3253921 A US3253921 A US 3253921A
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ultraviolet
compound
photographic
solvent
dispersion
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George W Sawdey
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to DEE23631A priority patent/DE1166623B/de
Priority to FR911542A priority patent/FR1356243A/fr
Priority to GB38132/62A priority patent/GB1026142A/en
Priority to JP6276864A priority patent/JPS4429620B1/ja
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D249/00Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18Benzotriazoles
    • C07D249/20Benzotriazoles with aryl radicals directly attached in position 2
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00Photosensitive materials
    • G03C1/76Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/815Photosensitive materials characterised by the base or auxiliary layers characterised by means for filtering or absorbing ultraviolet light, e.g. optical bleaching
    • G03C1/8155Organic compounds therefor
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/132Anti-ultraviolet fading

Definitions

  • UV radiation has a detrimental effect on photographic layers.
  • Ultraviolet radiation in light sources used for exposure of photographic products sometimes produces undesired exposure of the layer or layers of a photographic element. This is especially true in photographic elements designed for use in color photography in which the emulsion has been sensitized to the longer wavelength regions and it is desirable to record only the rays of the visible spectrum.
  • Color photographs on multilayer photographic material are susceptible to fading and discoloration by the action of ultraviolet radiation to which the photographs are subjected during viewing.
  • the residual couplers contained in the emulsion layer (in certain processes) after the formation of the picture images are attacked by ultraviolet radiation resulting in an undesirable stain in the finished photograph.
  • the action of ultraviolet radiation on finished color photographs is particularly noticeable on positive prints on paper or other opaque support since this type of print is frequently viewed in daylight which has a high content of ultraviolet radiation.
  • the dye-fading and discoloration elfects appear to be caused primarily by those Wavelengths of light close to the visual region of the spectrum, i.e., 300-400 III/1..
  • silver halide photographic materials can be protected from ultraviolet radiation by incorporating nondifiusing ultraviolet absorbing compounds in the silver halide emulsion layers or in overlying colloid coatmgs.
  • Ultraviolet absorbing compounds for photographic use must generally be colorless or nearly colorless, show good compatability with the medium in which they are incorporated, be inert to other photographic addenda in the element and in the processing solution, must have good ultraviolet absorptivity and be stable to ultraviolet radiation.
  • Representative compounds for incorporation in photographic elements are described, for example, in U.S. Patent 2,685,512, issued August 3, 1954; U.S. Patent 2,739,888, issued March 27, 1956; U.S. Patent 2,719,086, issued September 27, 1955; U.S. Patent 2,739,971, issued March 27, 1956; U.S. Patent 2,747,- 996, issued May 29, 1956, and U.S. Patent 2,784,087, issued March 5, 1957.
  • aromatic organic compounds like ultraviolet absorbers, dye-forming couplers, antistain agents, filter dyes, etc., have been made nondiffusing by addition of hydrophobic ballasting groups and require special techniques for incorporating them in a sufliciently high-dispersed form in aqueous photographic gelatin layers.
  • a typical procedure for accomplishing finely-divided particulate dispersions and avoiding unwanted crystallization or other aggregation of particles is the so-called Fischer method in which a nondiflusing compound is provided with a sulfonic acid or other solubilizing group so that it can be dissolved in water as the alkali metal salt Patented May 31, 1966 and the solution added to the aqueous gelatin coating composition.
  • Ultraviolet absorbing compounds suitable for addition to photographic emulsions and containing sulfonic or carboxylic acid functions to facilitate incorporation into photographic gelatin layers by the Fischer procedure are described in U.S. Patents, 2,685,512, issued August 3, 1954; 2,719,086, issued September 27, 1955; 2,739,888, issued March 27, 1956; 2,747,996, issued May 29, 1956; 2,784,087, issued March 5, 1957; 2,798,067, issued July 2, 1957; 2,808,330, issued October 1, 1957; and 2,875,053, issued February 24, 1959.
  • the Fischer method is convenient for incorporating ultraviolet absorbers in finely-divided and uniformly dispersed form and the resulting ultraviolet absorbing layers have shown good long-term stability.
  • Another technique employed in incorporating ultraviolet absorbing compounds into gelatin layers is by dissolving the absorber in a polar solvent, e.g., water and/or methanol, and then bathing the photographic gelatin coating in this solution.
  • a polar solvent e.g., water and/or methanol
  • This imbibition method is advantageous for the incorporation of ultraviolet absorbers into processed photographic strips for the purpose of protecting the images from the harmful effects of ultraviolet radiation.
  • This solvent dispersion technique has important technological advantages for introducing nondifiusing aromatic compounds into aqueous gelatin coating compositions.
  • the stability to light of ultraviolet absorbing compounds incorporated by this method is generally poorer than that of those incorporated by the Fischer method.
  • the poor stability of these compounds when dispersed by the solvent dispersion method may be due to the presence of organic solvent with the compound in the protective colloid.
  • the stability 4 The compounds of Formula I are incorporated in solvent dispersion advantageously by dissolving them in either a high boiling water-immiscible organic solvent, 21 low boiling organic solvent, or a water-soluble organic to light is excellent. 5 solvent, or in a mixture of a high boiling water-im- The related nonhydroxylated phenylbenzotriazoles do miscible organic solvent and/or a low boiling and/or not exhibit this stability advantage when incorporated b Water-soluble organic solvent. the solvent dispersion technique. Any of the high boiling Water-immiscible solvents The stability of my hydrophobic nondiffusing hydroxydescribed in U.S.
  • Patent 2,322,027 issued June 15, 1943, phenylbenzotriazole ultraviolet absorbers incorported by may be used as solvents.
  • the preferred solvents include the solvent dispersion technique is the result of the con1- di-n-butylphthalate, benzylphthalate, triphenyl phosphate, bination of this class of nondiffusing hydroxybenzotri tri-o-cresyl phosphate, diphenyl mono-p-tert-butyl phenyl azoles with the specific method of dispersing them.
  • An object of my invention is to provide novel photodiphenyl mono-o-chlorophenyl phosphate, monophenyl graphic elements protected against the harmful effects of di-o-chlorophenyl phosphate, tri-p-tert-butylphenyl phosultraviolet radiation by incorporation of ultraviolet abphate, tri-o-phenylphenyl phosphate, di-p-tert-butylphenyl sorbing materials.
  • Another object is to provide photomono(5-tert-butyl-2-phenylpheny1)phosphate, etc.
  • the organic solvents accomplished by the use of the solvent dispersion techniin include: que to incorporate in aqueous hydrophilic colloid solu- (1)
  • Low boiling substantially water-insoluble organic tions for coating silver halide emulsion layers or assosolvents such as methyl, ethyl, propyl and butyl acetates, ciated hydrophilic colloid layers, an ultraviolet-radiationisopropyl acetate, ethyl propionate, sec-butyl alcohol, absorbing compound represented by the following forethyl formate, butyl formate, nitromethane, nitroethane, mula: carbon tetrachloride, chloroform, etc., and (I) N OH (2) Water-soluble organic solvents, such as methyl l isobutyl ketone, fl-ethoxy ethyl acetate, fi-butoxy p-e
  • Thefollowing representative compounds of Formula I phenyl, 2 heXOXypheny1, g h h l etc an aryloxy listed in Table I vvill serve to illustrate the compounds group such as phenoxy, 4 methylphenoxy, z propylphen useful in my ultraviolet absorbing layers but are not conoxy, 3-amylphenoxy, etc., such that at least one of the sldered as llmlting 1116 inventiongroups, R, R and R shall contain at least 5 carbon N on R 1 atoms, and the total number of carbon atoms represented 4 3 ⁇ in R +R is at least 8. 2N
  • the compounds defined by Formula I are nondiflusing 6 u and have the solubility characteristics needed to carry out my invention advantageously.
  • a 9:1 methanol-water solution was made of each of my ultraviolet absorber compounds 1, 2, and 3, and the resulting solutions were imbibed into elatin layers by immersing the gelatin coating into the ultraviolet absorber solution. These coatings were subsequently dried, and Cary spectrophotometer traces were made for each of these coatings before and after 85 hours exposure to a xenon arc. The exposure resulted in considerable loss in the usefulness of these layers for photographic materials.
  • Coatings 2, 4 and 7 were made by the same procedure excepting that the amount of absorber used was increased in the coating composition so that the coatings contained 100 mg./ft. of the absorber instead of mg./ft.
  • Coating 5 was made by a procedure similar to that used for Coating 1 but the coating composition contained no tri-o-cresyl phosphate. The amount of absorber was increased so it would coat at mg./ft.
  • Coating 9 was made from the dispersion described below.
  • a dispersion was made by dissolving 1.0 g. of 2-(2-hydroxy-5-iso-octyl x sulfophenyl)benzotriazole, sodium salt in a solution containing 22 ml. of 10 percent gelatin, 2 ml. of 5 percent propylated naphthylene sulfonate, 2 ml. of 7.5 percent saponin and 14 ml. of water.
  • This mixture was coated on a clear film support to a wet thickness of 0.003 of an inch.
  • the coating contained 100 mg./ft. of ultraviolet absorber and 200 mg./ft. of gelatin.
  • Coatings 8 and 9 which fall outside my invention both show poor stability as evidenced by the serious losses in density in the ultraviolet region produced by exposure to xenon arc. Even more serious losses are shown by other absorbing compounds selected from outside the invention as is shown by Coatings 10 through 15. (See Table III below.)
  • Coatings 10 through were made for typical ultraviolet absorbers (identified in Table III) selected from outside the invention.
  • Coatings 10 and 12 through 15 were from the composition described coated at mg/ft. of ultraviolet absorbing compounds except that in Coating 11 composition, n-butyl acetate was used as the organic solvent instead of tri-o-cresylphosphate.
  • Coating 16 is identical with Coating l0.
  • Coatings 17 and 18 were made according to the procedure described for Coating 9, using Fischer dispersions of ultraviolet absorbers having the same structure as the ultraviolet absorbing compound of Coating 10 but containing sulfonic acid water-solubilizing groups.
  • the changes in transmis sion density produced by 64 hours exposure to xenon arc was determined as described previously and are shown in Table IV.
  • cetylZ-phenyIiminQ-L thliizolidone sodium sa l8 5-(2,4-disulfobenzylidene)- d0 2. 6
  • the 5-(2-sulfobenzylidene) derivative, incorporated by the Fischer technique showed the better stability to light of the Fischer ultraviolet absorber coating over the ultraviolet absorber coating incorporated by solvent dispersion technique.
  • Tables II and III show that hours exposure to a xenon are produced only from O to 2.3 percent loss in density at A370 m, for my coatings compared to losses of from 59.2 to 83.0 percent for coatings made from solvent dispersions of ultraviolet absorbers outside the invention.
  • Coating 8 (outside the invention) from a solvent dispersion of an ultraviolet absorber outside the invention showed a 26 percent loss in density
  • Coating 9 (outside the invention) which was made from a Fischer dispersion of ultraviolet absorbing compound showed a 28 percent loss in specular density after only 72 hours exposure to the xenon arc.
  • Table IV shows that 64 hours exposure to xenon are produced only 2.6 to 3 percent loss in density at A370 mg for Fischer coatings containing absorbers of the type known in the art while solvent dispersion coatings of the organic solvent-soluble analog are very unstable to light and showed a 58.5 percent loss in density.
  • Example 2 The solvent dispersions for Coatings 19-22 of the following Table V were made for representative compounds of my invention, and a typical ultraviolet absorber of the prior art (Coating 22).
  • One gram of ultraviolet absorber was dissolved in a mixture of 10 ml. of acetone and 9 ml. of methanol.
  • Cary spectrophotometer traces as described in Example 1 were made for these solvent dispersion coatings and the percent loss in transmission density at a wavelength of 370 m was determined after xenon are fading. These values are tabulated in the following table.
  • Example 3 One gram of 2-(2-hydroxy-5'-iso-octylphenyl) benzotriazole, Compound 1, was dissolved by heating in 2 ml. of tri-o-cresyl phosphate to about 120 C. This solution was added to 20 ml. of ten percent gelatin and milled five times. The resulting dispersion was diluted with an equal volume of water and coated on both clear and opaque film support. These coatings had negligible absorption in the visual region and showed no change in absorption after 60 hours irradiation from a xenon arc.
  • a spectral absorption curve for this coating showed strong absorption of radiation in the region from 210 to 380 m with absorption peaks at 220, 296, and 335 III/1., respectively.
  • the following example illustrates the use of a low boiling solvent or auxiliary solvent along with the high boiling solvent in the preparation of a dispersion of the ultraviolet light absorbing compound.
  • Example 4 A multilayer element for color photography containing incorporated color forming couplers and an ultraviolet absorbing layer was prepared. On a paper support were coated in succession, layer 1 consisting of a blue-sensitive, silver bromide gelatin emulsion containing a yellow image-forming coupler (such as is described in Weiss- .berger US. Patent 2,298,443, issued October 13, 1942, McCrossen et al. US.
  • layer 1 consisting of a blue-sensitive, silver bromide gelatin emulsion containing a yellow image-forming coupler (such as is described in Weiss- .berger US. Patent 2,298,443, issued October 13, 1942, McCrossen et al. US.
  • Patent 2,875,057, issued February 24, 1959, etc. dissolved in a high boiling solvent, such as di-n-butylphthalate, layer 2 a gelatin interlayer, layer 3 a green-sensitive, silver chlorobromide gelatin emulsion containing a pyrazolone (magenta-forming) coupler (such as is described in Porter et al. US. Patent 2,369,489, issued February 13, 1945, and others) dissolved in tri-ocresyl phosphate, layer 4 an ultraviolet absorbing layer, layer 5 a red-sensitized, silver chlorobromide gelatin emulsion containing a cyan-forming phenolic coupler (such as is described in Salminen et al. US. Patent 2,423,730, issued July 8, 1947, and others) dissolved in a suitable high boiling solvent such as di-n-butylphthalate, and layer 6 protective gelatin overcoat.
  • a high boiling solvent such as di-n-butylphthalate
  • layer 2
  • the coupler dispersions were made according to the dispersion techniques described previously.
  • sample A had as layer 4 an ultraviolet absorbing layer made as Coating 1 of Table II but containing 100 mg. of ultraviolet absorber per ft. of coating
  • sample B had as layer 4, coating 10 of Table III but containing 100 mg. of ultraviolet absorber per ft. of coating.
  • Sample Coatings A and B were given identical exposure to light through a silver step wedge so that the coating under the densest area of the step wedge received no exposure.
  • the samples were given identical processing, comprising development in a developer having the composition:
  • Binders that are particularly advantageous to use in clude gelatin, albumin, etc., cellulose derivatives, polyvinyl compounds, etc.
  • the polymeric binders include polyvinyl alcohol or a hydrolyzed polyvinyl acetate as described in Lowe US. Patent 2,286,215, issued June 16, 1942; a far hydrolyzed cellulose ester such as cellulose acetate hydrolyzed to an acetyl content of 19-26 percent as described in U.S. Patent 2,327,808 of Lowe and Clark, issued August 24, 1943; a water-soluble ethanolamine cellulose acetate as described in Yutzy US. Patent 2,322,- 085, issued June 15, 1943; a polyacrylamide having a.
  • Patent 2,808,331 issued October 1, 1957; or a polymeric material which results from polymerizing a protein or a saturated acylated protein with a monomer having a vinyl group as described in U.S. Patent 2,852,382, of Illingsvvorth, Dann and Gates, issued September 16, 1958.
  • the dispersion of an absorbing compound of Formula I in the binder material is coated over the light-sensitive layer of the photographic element.
  • the ultraviolet filter layer need not be an outer layer, but can be used as an interlayer, i.e., under the layer or layers not needing the protection and over the layer or layers needing protection.
  • the ultraviolet filter layer can be placed between the blueand green-sensitive layers or between the greenand red-sensitive layers.
  • the ultraviolet filter layer can be over all three layers or between any two of the layers.
  • the ultraviolet absorbing composition can be incorporated directly in the light-sensitive emulsion instead of, or in addition, being present in 1 1 another layer.
  • the amount of the ultraviolet absorbing material used can be varied, depending upon the effect desired and the use that will be made of the material.
  • My ultraviolet absorbing compositions are coated over a wide range of concentrations; usually they are coated in the range of from 20 to 300 mg. of ultraviolet absorbing compound per ft. photographic element. A preferred range is from 75 to 160 mg./ft.
  • the optimum coating concentrations will depend upon the particular photographic element to be protected and the amount of protection desired. The optimum coating concentrations for a given photographic element can be determined by methods well known in the art.
  • photographic elements may have as their support any of the conventional support materials, such as film supports, e.g., cellulose acetate, etc., opaque supports, such as white pigmented film, paper, etc.
  • film supports e.g., cellulose acetate, etc.
  • opaque supports such as white pigmented film, paper, etc.
  • Compound 1 was prepared as follows. Seven grams (0.1 mole) of sodium nitrite was added slowly to 44 ml. of concentrated sulfuric acid. The temperature rose to 70 C. When the mixture became clear, it was cooled to 20, and 13.8 g. (0.1 mole) of o-nitroaniline was added With vigorous stirring. The ensuing syrupy reaction mixture was added to 240 g. of ice.
  • the above diazonium solution was added with stirring to a solution prepared by dissolving 20.8 g. (0.1 mole) of 4-isooctylphenol in 100 ml. of methanol. This solution was then added to a solution of 200 g. of sodium acetate in 200 ml. of water. The red solid which precipitated was recrystallized from methanol giving 17.5 g. of red needles, M.P. 96-97 C. The yield was 49.3 percent of the theoretical.
  • Compound 2 was prepared by the same method as Compound 1 but using 4-n-octylphenol in place of 4-isooctylphenol.
  • Compound 2 had a M.P. of 8687 C.
  • Compound 3 was prepared by the method used to make Compound 1 but using 2,4-di-tert-amylphenol in place of the 4-octylphenol.
  • Compound 4 had a M.P. of 77-78 C.
  • Compound 4 was prepared by the method used to make Compound 1 but using 4-dodecylphenol in place of the 4-octylphenol.
  • the product had a M.P. of 7277 C.
  • Compound 5 was prepared similarly to Compound 1 but substituting 4-hexadecylphenol for the 4-octylphenol.
  • the product had a M.P. of 6970 C.
  • Compound 6 may be prepared similarly to Compound 1 but substituting Z-tert-amyl-4-benzylphenol for the 4- octylphenol.
  • Compound 7 may be prepared similarly to Compound 1 but substituting 2-tert-amyl-4-phenylphenol for the 4- octylphenol.
  • Compound 8 may be prepared similarly to Compound 1 but using 4-a-mino-5-nitrotoluene in place of o-nitroaniline.
  • Compound 9 may be prepared similarly to Compound 1 but using 2-nitro-4-isooctylan'iline in place of o-nitroaniline.
  • the 2-nitro-4-isooctylaniline is prepared by nitrating issoctylbenzene, isolating the 4-nitroisooctylbenzene, reduction of this to the amino compound, acetylation of the amino group, nitration to make the 2-nitro derivative followed by hydrolysis.
  • Compound 10 may be prepared similarly to Compound 1 but using 2-nitro-4-carbobutoxy aniline in place of 0- nitroaniline and 2-n-butyl-4-tert-arnylphenol in place of the 4-octylphenol.
  • Compound 11 may be prepared similarly to Compound 1 but using 2-nitro-4-chloroaniline in place of o-nitroaniline and 2-n-amyl-4-phenylphenol in place of the 4- octylphenol.
  • Compound 12 may be prepared similarly to Compound 1 but using 2-nitro-4-methoxyaniline in place of o-nitroaniline and 2,4-di-tert-amylphenol in place of 4-octylphenol.
  • Compound 13 may be prepared similarly to Compound 1 but using 2,4-dinitroaniline in place of o-nitroaniline and 2-n-octyl-4-methoxyphenol in place of 4-octylphenol.
  • Compound 14 may be prepared similarly to Compound 1 but using 4-chloro-2-nitroaniline in place of o-nitroaniline and 2-tert-butyl-4-cyclohexylphenol in place of 4- octylphenol.
  • Compound 15 may be prepared similarly to Compound 1 but using 2-nitro-4-methylaniline instead of o-nitroaniline and 2-chloro-4-octylphenol in place of 4-octylphenol.
  • Compound 16 may be prepared similarly to Compound 1 but using 2-nitro-4-phenylaniline instead of o-nitroaniline and 2,4-di-tert-amylphenol instead of 4-octylphenol.
  • Compound 17 may be prepared similarly to Compound 1 but using 2-nitro-4-methylaniline instead of o-nitroaniline and 2-tert-amyl-4-phenoxyphenol instead of 4- octylphenol.
  • the ultraviolet absorbing compounds of Formula I are characterized by their nonditfusi'bility in coated layers, good stability in the incorporating solvents, and their good ultraviolet absorption.
  • Ultraviolet absorbing layers containing compounds of Formula I incorporated according to the preferred methods of my invention have unexpectedly excellent stability upo'n prolonged exposure to ultraviolet radiation which makes them ideally suited for protecting photographic elements, particularly dye images in color materials.
  • the amount of solvent to be retained in the final coating made according to my invention can be adjusted according to the requirements of the product and by selecting solvents or a mixture of solvents of appropriate volatility and/or water solubility.
  • Some ultraviolet absorbing layers made in the same manner using prior art absorbers as described in Example 1 showed from 59 to 83 percent loss in specular density at an arbitrarily selected near-visible wave length of 370 m as a result of hours exposure to a xenon arc while my layers showed only from 0 to 2.3 percent loss under the same conditions.
  • UV absorbing layers made by the incorporation of water-solubilized derivatives, e.g., 2 (2-hydroxy-5'-isooctyl-X-sulfophenyl)benzotriazole, sodium salt, of the same ultraviolet absorbing compounds directly in a colloidal binder have shown poor stability as indicated by a serious loss in specular density at the A 370 m after only 72 hours exposure to a xenon arc.
  • compounds analogous to Formula I, but without the 2-hydroxy substituent on the 2-phenyl ring, e.g., as used in Coating 8 of Example 1- showed a seriou loss in density after only 64 hours exposure to a xenon arc.
  • An ultraviolet absorbing dispersion comprising a hydrophilic colloid binder material and a hydrophobic compound selected from those having the formula:
  • R, R and R each represents a member selected from the class consisting of a hydrogen atom, a halogen atom, a nitro group, an alkyl group having from 1 to 18 carbon atoms, an alkoxy group having from 1 to 18 carbon atoms, an aryl group, and an aryloxy group such that at least one of the groups R, R and R contains at least 5 carbon atoms and the total number of carbon atoms represented in R +R is at least 8.
  • An ultraviolet absorbing dispersion comprising a hydrophilic colloid binder material, a solvent and a hydrophobic compound selected from those having the formula:
  • R, R and R each represents a member selected from the class consisting of a hydrogen atom, a halogen atom, a nitro group, an alkyl group having from 1 to 18 carbon atoms, an alkoxy group having from 1 to 18 carbon atoms, an aryl group, and an aryloxy group such that at least one of the groups R, R and R contain at least 5 carbon atoms and the total number of carbon atoms represented in R +R is at least 8.
  • a photographic element protected against ultraviolet radiation by a protective amount of a dispersion of claim 1.
  • a photographic element comprising a support, at least one hydrophilic colloid photographic silver halide emulsion layer, and incorporated in one of the hydrophilic colloid layers of said photographic element a hydrophobic compound selected from those represented by the following formula:
  • R, R and R each represents a member selected from the class consisting of a hydrogen atom, a halogen atom, a nitro group, an alkyl group having from 1 to 18 carbon atoms, an alkoxy group having from 1 to 18 carbon atoms, an aryl group, and an aryloxy group such that at least one of the groups R, R and R contains at least 5 carbon atoms and the total number of carbon atoms represented in R +R is at least 8.
  • a photographic element comprising a support, at least one photographic silver halide emulsion layer, superposed on said support, and an outer gelatin layer containing a hydrophobic compound selected from those represented by the formula:
  • R, R and R each represents a member selected from the class consisting of a hydrogen atom, a halogen atom, a nitro group, an alkyl group having from 1 to 18 carbon atoms, an alkoxy group having from 1 to 18 carbon atoms, an aryl group, and an aryloxy group such that at least one of the groups R, R and R contain at least 5 carbon atoms and the total number of carbon atoms represented in R +R is at least 8.
  • a finished photographic element comprising a support having thereon a plurality of developed and fixed photographic emulsion layers containing developed-dye images, at least one of said dye images being subject to fading by the action of ultraviolet radiation, said emulsion layer containing a developed-dye image subject to fading lying between said support and a gelatin layer containing an ultraviolet absorbing hydrophobic compound selected from those represented by the following formula:
  • R, R and R each represents a member selected from the class consisting of a hydrogen atom, a halogen atom, a nitro group, an alkyl group having from 1 to 18 carbon atoms, an alkoxy group having from 1 to 18 carbon atoms, an aryl group, and an aryloxy group such that at least one of the groups R, R and R contain at least 5 carbon atoms and the total number of carbon atoms represented in R +R is at least 8.
  • a photographic element comprising a support, a photographic gelatino-silver halide emulsion layer, and a hydrophilic colloid layer containing a dispersion of 2-(2'- hydroxy-S -iso-octylphenyl benzotriazole.
  • a photographic element comprising a support, a photographic gelatino-silver halide emulsion layer, and a hydrophilic colloid layer containing a dispersion of 2-(2- hydroxy-3 ',5'-di-tert-amlyphenyl benzotriazole.
  • a photographic element comprising a su port, a photographic gelatino-silver halide emulsion layer, and a 15 hydrophilic colloid layer containing a dispersion of 2-(2- hydroxy--dodecylphenyl)benzotriazole.
  • a photographic element comprising a support, a photographic gelatino-silver halide emulsion layer, and a hydrophilic colloid layer containing a dispersion of 2-(2'- hydroxy-S'-hexadecylphenyl benzotriazole.
  • a photographic element comprising a support, a photographic gelatino-silver halide emulsion layer, and a hydrophilic colloid layer containing a dispersion of 5- methyl 2 (2 hydroXy 5' iso octylphenyl) benzotriazole.
  • a method of preventing image degradation in a finished photographic element comprising a plurality of developed and fixed photographic emulsion layers containing developed-dye images, at least one of said dye images being subject to fading by the action of ultraviolet radiation, said emulsion layer containing a developed-dye image subject to fading lying between a support and a gelatin outer layer, which comprises applying to said photographic element a hydrophilic colloidal binder material containing a solvent dispersion of a hydrophobic compound selected from those having the formula:
  • An aqueous gelatin coating composition comprising a dispersion of water, gelatin and an ultraviolet absorbing hydrophobic compound selected from those having the formula:
  • R, R and R each represents a member selected from the class consisting of a hydrogen atom, a halogen atom, a nitro group, an alkyl group having from 1 to 18 carbon atoms, an alkoxy group having from 1 to 18 carbon atoms, an aryl group, and an aryloxy group such that at least one of the groups R, R and R contains at least 5 carbon atoms and the total number of carbon atoms represented in R +R is at least 8.
  • An aqueous gelatin coating composition of claim 18 containing an organic solvent for said ultraviolet absorbing compound.

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US144228A 1961-10-10 1961-10-10 Novel photographic elements protected against ultraviolet radiation Expired - Lifetime US3253921A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
BE623419D BE623419A (de) 1961-10-10
US144228A US3253921A (en) 1961-10-10 1961-10-10 Novel photographic elements protected against ultraviolet radiation
DEE23631A DE1166623B (de) 1961-10-10 1962-10-04 Ultraviolettstrahlung absorbierendes Filter fuer photographische Zwecke
FR911542A FR1356243A (fr) 1961-10-10 1962-10-08 Nouveau film photographique protégé contre l'ultraviolet
GB38132/62A GB1026142A (en) 1961-10-10 1962-10-09 Ultraviolet light absorbing compositions and their use in photographic materials
JP6276864A JPS4429620B1 (de) 1961-10-10 1964-11-07

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US3253921A true US3253921A (en) 1966-05-31

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BE (1) BE623419A (de)
DE (1) DE1166623B (de)
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GB (1) GB1026142A (de)

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US3533794A (en) * 1968-03-25 1970-10-13 Fuji Photo Film Co Ltd Color photographic light-sensitive material containing ultraviolet absorbing agents
US3649276A (en) * 1968-08-10 1972-03-14 Fuji Photo Film Co Ltd COLOR PHOTOGRAPHIC SILVER HALIDE LIGHT-SENSITIVE MATERIALS CONTAINING p-AMINDIENZOYL ACETANILIDE COLOR COUPLERS
US4096242A (en) * 1974-08-23 1978-06-20 Gaf Corporation Stabilized product of manufacture containing a branched chain dodecyl isomeric mixture of (dodecyl-hydroxyphenyl)-benzo-triazole and a heat or light sensitive material
DE2805726A1 (de) * 1977-02-10 1978-08-17 Konishiroku Photo Ind Verfahren zur herstellung eines lichtempfindlichen photographischen silberhalogenidmaterials sowie das dabei erhaltene lichtempfindliche photographische silberhalogenidmaterial
US4208210A (en) * 1974-12-19 1980-06-17 Fuji Photo Film Co., Ltd. Process for forming an optical soundtrack
US4220711A (en) * 1978-03-09 1980-09-02 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive element
WO1981001473A1 (en) * 1979-11-09 1981-05-28 Minnesota Mining & Mfg Uv-absorbing compounds and photographic elements containing them
FR2483637A1 (fr) * 1980-05-30 1981-12-04 Asahi Chemical Ind Materiau de formation d'une image a sec
US4315848A (en) * 1979-05-10 1982-02-16 Ciba-Geigy Corporation 2-[2-Hydroxy-3,5-di-(α,α-dimethylbenzyl)-phenyl]-2H-benzotriazole and stabilized compositions
US4330608A (en) * 1979-08-24 1982-05-18 Xerox Corporation Benzotriazole stabilized photosensitive device
US4383863A (en) * 1979-12-17 1983-05-17 Ciba-Geigy Corporation 2-[2-Hydroxy-3,5-di-tert-octylphenyl]-2H-benzotriazole in stabilized photographic compositions
US4414393A (en) * 1981-11-05 1983-11-08 Ciba-Geigy Corporation Ultraviolet-absorbing stabilizers substituted by an aliphatic hydroxyl group
JPS58208745A (ja) * 1982-05-28 1983-12-05 Konishiroku Photo Ind Co Ltd カラ−写真感光材料
EP0095920A2 (de) * 1982-06-01 1983-12-07 Konica Corporation Farbphotographisches lichtempfindliches Material
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EP0106690A2 (de) * 1982-10-15 1984-04-25 Konica Corporation Verfahren zur Erzeugung eines erhöhten Aufhelleffekts und photographisches Silberhalogenidmaterial mit erhöhtem Aufhelleffekt
US4447511A (en) * 1981-03-06 1984-05-08 Ciba-Geigy Corporation 2-[2-Hydroxy-3,5-di-tert-octylphenyl]-2H-benzotriazole in stabilized photographic compositions
US4486518A (en) * 1981-02-20 1984-12-04 Polychrome Corporation Duplicating film mask with radiation absorbing benzophenone in processed positive-working radiation sensitive layer on transparent substrate
US4496676A (en) * 1981-11-05 1985-01-29 Ciba-Geigy Corporation Ultraviolet-absorbing stabilizers substituted by an aliphatic hydroxyl group
US4496757A (en) * 1981-11-05 1985-01-29 Ciba-Geigy Corporation Ultraviolet-absorbing stabilizers substituted an aliphatic hydroxyl group
US4518686A (en) * 1982-06-05 1985-05-21 Konishiroku Photo Industry Co., Ltd. Color photographic light-sensitive material containing UV filter compounds
US4544691A (en) * 1981-11-05 1985-10-01 Ciba-Geigy Corporation Compositions containing ultraviolet-absorbing stabilizing substituted by an aliphatic hydroxyl group
US4576908A (en) * 1983-06-07 1986-03-18 Minnesota Mining And Manufacturing Company Ultraviolet absorber in photographic elements
US4587208A (en) * 1982-06-02 1986-05-06 Konishiroku Photo Industry Co., Ltd. Color photographic light-sensitive material
US4587346A (en) * 1985-01-22 1986-05-06 Ciba-Geigy Corporation Liquid 2-(2-hydroxy-3-higher branched alkyl-5-methyl-phenyl)-2H-benzotriazole mixtures, stabilized compositions and processes for preparing liquid mixtures
EP0210660A2 (de) 1985-07-31 1987-02-04 Fuji Photo Film Co., Ltd. Verfahren zur Bildung eines Bildes
US4840870A (en) * 1983-12-19 1989-06-20 Konishiroku Photo Industry Co., Ltd. Heat-transfer image-receiving element
US4859759A (en) * 1988-04-14 1989-08-22 Kimberly-Clark Corporation Siloxane containing benzotriazolyl/tetraalkylpiperidyl substituent
US4933271A (en) * 1987-09-30 1990-06-12 Ciba-Geigy Ag Stabilizers for color photography recording materials
US4968704A (en) * 1988-08-13 1990-11-06 Pfizer Inc. Pyridine compounds which are useful as anti-arrhythmic agents
US4973701A (en) * 1988-04-11 1990-11-27 Ciba-Geigy Corporation Liquid substituted 2H-benzotriazole mixtures, stabilized compositions and processes for preparing the liquid mixtures
US5095062A (en) * 1988-04-11 1992-03-10 Ciba-Geigy Corporation Stabilized compositions containing liquid substituted 2H-benzotriazole mixtures
US5149828A (en) * 1987-09-30 1992-09-22 Ciba-Geigy Ag Stabilizers for color photography recording materials
US5240975A (en) * 1988-04-11 1993-08-31 Ciba-Geigy Corporation Liquid substituted 2H-benzotriazole mixtures, stabilized compositions
US5384235A (en) * 1992-07-01 1995-01-24 Eastman Kodak Company Photographic elements incorporating polymeric ultraviolet absorbers
US5468604A (en) * 1992-11-18 1995-11-21 Eastman Kodak Company Photographic dispersion
US5492804A (en) * 1994-06-30 1996-02-20 Minnesota Mining And Manufacturing Company Chromogenic leuco redox-dye-releasing compounds for photothermographic elements
US5492805A (en) * 1994-06-30 1996-02-20 Minnesota Mining And Manufacturing Company Blocked leuco dyes for photothermographic elements
US5492803A (en) * 1995-01-06 1996-02-20 Minnesota Mining And Manufacturing Company Hydrazide redox-dye-releasing compounds for photothermographic elements
EP0772080A2 (de) 1995-11-02 1997-05-07 Eastman Kodak Company Photographisches Element verwendbar als Kinofilm
EP0779540A1 (de) 1995-12-14 1997-06-18 Agfa-Gevaert N.V. Eine neue Klasse nicht-sensibilisierenden infrarot Farbstoffen zur Verwendung in lichtempfindlichen Elementen
US5731137A (en) * 1995-08-18 1998-03-24 Fuji Photo Film Co., Ltd. Emulsified dispersion and silver halide color photographic light-sensitive material containing the same
EP0846571A1 (de) 1996-12-04 1998-06-10 Agfa-Gevaert N.V. Verfahren zur Herstellung eines durch Wärme erzeugten verbesserten Bildes
US5766834A (en) * 1996-05-17 1998-06-16 Eastman Kodak Company Photographic element containing ultraviolet absorbing polymer
US5772920A (en) * 1995-07-12 1998-06-30 Clariant Finance (Bvi) Limited U.V. absorber compositions
US5814438A (en) * 1996-03-29 1998-09-29 Eastman Kodak Company Benzotriazole-based novel UV absorbers and photographic elements containing them
US5858633A (en) * 1994-12-21 1999-01-12 Eastman Kodak Company Photographic elements containing 3-alkyl group substituted 2-hydroxyphenylbenzotriazole UV absorbing polymers
US5928857A (en) * 1994-11-16 1999-07-27 Minnesota Mining And Manufacturing Company Photothermographic element with improved adherence between layers
US6117624A (en) * 1993-06-04 2000-09-12 Eastman Kodak Company Infrared sensitized, photothermographic article
US6171707B1 (en) 1994-01-18 2001-01-09 3M Innovative Properties Company Polymeric film base having a coating layer of organic solvent based polymer with a fluorinated antistatic agent
US6242065B1 (en) 1998-10-07 2001-06-05 Bmc Vision-Ease Lens, Inc. Lens blanks for ophthalmic elements
USRE37693E1 (en) * 1982-06-05 2002-05-07 Konishiroku Photo Industry Co., Ltd. Color photographic light-sensitive material containing UV filter compounds
WO2013103139A1 (ja) 2012-01-06 2013-07-11 コニカミノルタアドバンストレイヤー株式会社 フィルムミラー、フィルムミラーの製造方法、太陽熱発電用フィルムミラー及び太陽熱発電用反射装置
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US2940815A (en) * 1953-12-04 1960-06-14 Gen Aniline & Film Corp Vat dye compositions containing benzotriazoles
US2947628A (en) * 1956-10-12 1960-08-02 Eastman Kodak Co Multilayer print film having incorporated coloring material
US3004896A (en) * 1956-12-14 1961-10-17 Geigy Ag J R Ultra-violet light-absorbing composition of matter
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Cited By (66)

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Publication number Priority date Publication date Assignee Title
US3533794A (en) * 1968-03-25 1970-10-13 Fuji Photo Film Co Ltd Color photographic light-sensitive material containing ultraviolet absorbing agents
US3649276A (en) * 1968-08-10 1972-03-14 Fuji Photo Film Co Ltd COLOR PHOTOGRAPHIC SILVER HALIDE LIGHT-SENSITIVE MATERIALS CONTAINING p-AMINDIENZOYL ACETANILIDE COLOR COUPLERS
US4096242A (en) * 1974-08-23 1978-06-20 Gaf Corporation Stabilized product of manufacture containing a branched chain dodecyl isomeric mixture of (dodecyl-hydroxyphenyl)-benzo-triazole and a heat or light sensitive material
US4208210A (en) * 1974-12-19 1980-06-17 Fuji Photo Film Co., Ltd. Process for forming an optical soundtrack
DE2805726A1 (de) * 1977-02-10 1978-08-17 Konishiroku Photo Ind Verfahren zur herstellung eines lichtempfindlichen photographischen silberhalogenidmaterials sowie das dabei erhaltene lichtempfindliche photographische silberhalogenidmaterial
US4220711A (en) * 1978-03-09 1980-09-02 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive element
US4315848A (en) * 1979-05-10 1982-02-16 Ciba-Geigy Corporation 2-[2-Hydroxy-3,5-di-(α,α-dimethylbenzyl)-phenyl]-2H-benzotriazole and stabilized compositions
US4330608A (en) * 1979-08-24 1982-05-18 Xerox Corporation Benzotriazole stabilized photosensitive device
US4323633A (en) * 1979-11-09 1982-04-06 Minnesota Mining And Manufacturing Company UV-Absorbing compounds and photographic elements containing them
WO1981001473A1 (en) * 1979-11-09 1981-05-28 Minnesota Mining & Mfg Uv-absorbing compounds and photographic elements containing them
US4383863A (en) * 1979-12-17 1983-05-17 Ciba-Geigy Corporation 2-[2-Hydroxy-3,5-di-tert-octylphenyl]-2H-benzotriazole in stabilized photographic compositions
FR2483637A1 (fr) * 1980-05-30 1981-12-04 Asahi Chemical Ind Materiau de formation d'une image a sec
US4486518A (en) * 1981-02-20 1984-12-04 Polychrome Corporation Duplicating film mask with radiation absorbing benzophenone in processed positive-working radiation sensitive layer on transparent substrate
US4447511A (en) * 1981-03-06 1984-05-08 Ciba-Geigy Corporation 2-[2-Hydroxy-3,5-di-tert-octylphenyl]-2H-benzotriazole in stabilized photographic compositions
US4414393A (en) * 1981-11-05 1983-11-08 Ciba-Geigy Corporation Ultraviolet-absorbing stabilizers substituted by an aliphatic hydroxyl group
US4544691A (en) * 1981-11-05 1985-10-01 Ciba-Geigy Corporation Compositions containing ultraviolet-absorbing stabilizing substituted by an aliphatic hydroxyl group
US4496757A (en) * 1981-11-05 1985-01-29 Ciba-Geigy Corporation Ultraviolet-absorbing stabilizers substituted an aliphatic hydroxyl group
US4496676A (en) * 1981-11-05 1985-01-29 Ciba-Geigy Corporation Ultraviolet-absorbing stabilizers substituted by an aliphatic hydroxyl group
JPH058415B2 (de) * 1982-05-28 1993-02-02 Konishiroku Photo Ind
US4456681A (en) * 1982-05-28 1984-06-26 Konishiroku Photo Industry Co., Ltd. Color photographic materials
JPS58208745A (ja) * 1982-05-28 1983-12-05 Konishiroku Photo Ind Co Ltd カラ−写真感光材料
EP0095920A3 (en) * 1982-06-01 1984-04-18 Konishiroku Photo Industry Co. Ltd. A color photographic light-sensitive material
EP0095921A3 (en) * 1982-06-01 1984-03-28 Konishiroku Photo Industry Co. Ltd. Color photographic light-sensitive material
EP0095921A2 (de) * 1982-06-01 1983-12-07 Konica Corporation Farbphotographisches lichtempfindliches Material
EP0095920A2 (de) * 1982-06-01 1983-12-07 Konica Corporation Farbphotographisches lichtempfindliches Material
US4587208A (en) * 1982-06-02 1986-05-06 Konishiroku Photo Industry Co., Ltd. Color photographic light-sensitive material
USRE37693E1 (en) * 1982-06-05 2002-05-07 Konishiroku Photo Industry Co., Ltd. Color photographic light-sensitive material containing UV filter compounds
US4518686A (en) * 1982-06-05 1985-05-21 Konishiroku Photo Industry Co., Ltd. Color photographic light-sensitive material containing UV filter compounds
EP0231956A3 (en) * 1982-10-15 1989-01-25 Konishiroku Photo Industry Co. Ltd. Method of providing an increased brightening effect in silver halide photographic materials
EP0231956A2 (de) * 1982-10-15 1987-08-12 Konica Corporation Verfahren zur Erzeugung eines erhöhten Aufhelleffekts in photographischen Silberhalogenidmaterialien
EP0106690A2 (de) * 1982-10-15 1984-04-25 Konica Corporation Verfahren zur Erzeugung eines erhöhten Aufhelleffekts und photographisches Silberhalogenidmaterial mit erhöhtem Aufhelleffekt
EP0106690A3 (en) * 1982-10-15 1984-09-05 Konishiroku Photo Industry Co. Ltd. Method of providing an increased brightening effect and silver halide photographic material having increased brightening effect
US4576908A (en) * 1983-06-07 1986-03-18 Minnesota Mining And Manufacturing Company Ultraviolet absorber in photographic elements
US4840870A (en) * 1983-12-19 1989-06-20 Konishiroku Photo Industry Co., Ltd. Heat-transfer image-receiving element
US4587346A (en) * 1985-01-22 1986-05-06 Ciba-Geigy Corporation Liquid 2-(2-hydroxy-3-higher branched alkyl-5-methyl-phenyl)-2H-benzotriazole mixtures, stabilized compositions and processes for preparing liquid mixtures
EP0210660A2 (de) 1985-07-31 1987-02-04 Fuji Photo Film Co., Ltd. Verfahren zur Bildung eines Bildes
US4933271A (en) * 1987-09-30 1990-06-12 Ciba-Geigy Ag Stabilizers for color photography recording materials
US5149828A (en) * 1987-09-30 1992-09-22 Ciba-Geigy Ag Stabilizers for color photography recording materials
US5240975A (en) * 1988-04-11 1993-08-31 Ciba-Geigy Corporation Liquid substituted 2H-benzotriazole mixtures, stabilized compositions
US4973701A (en) * 1988-04-11 1990-11-27 Ciba-Geigy Corporation Liquid substituted 2H-benzotriazole mixtures, stabilized compositions and processes for preparing the liquid mixtures
US5095062A (en) * 1988-04-11 1992-03-10 Ciba-Geigy Corporation Stabilized compositions containing liquid substituted 2H-benzotriazole mixtures
US4859759A (en) * 1988-04-14 1989-08-22 Kimberly-Clark Corporation Siloxane containing benzotriazolyl/tetraalkylpiperidyl substituent
US4968704A (en) * 1988-08-13 1990-11-06 Pfizer Inc. Pyridine compounds which are useful as anti-arrhythmic agents
US5384235A (en) * 1992-07-01 1995-01-24 Eastman Kodak Company Photographic elements incorporating polymeric ultraviolet absorbers
US5468604A (en) * 1992-11-18 1995-11-21 Eastman Kodak Company Photographic dispersion
US6117624A (en) * 1993-06-04 2000-09-12 Eastman Kodak Company Infrared sensitized, photothermographic article
US6171707B1 (en) 1994-01-18 2001-01-09 3M Innovative Properties Company Polymeric film base having a coating layer of organic solvent based polymer with a fluorinated antistatic agent
US5492804A (en) * 1994-06-30 1996-02-20 Minnesota Mining And Manufacturing Company Chromogenic leuco redox-dye-releasing compounds for photothermographic elements
US5492805A (en) * 1994-06-30 1996-02-20 Minnesota Mining And Manufacturing Company Blocked leuco dyes for photothermographic elements
US5696289A (en) * 1994-06-30 1997-12-09 Minnesota Mining And Manufacturing Company Blocked leuco dyes for photothermographic elements
US5705676A (en) * 1994-06-30 1998-01-06 Minnesota Mining And Manufacturing Company Chromogenic leuco redox-dye-releasing compounds for photothermographic elements
US5928857A (en) * 1994-11-16 1999-07-27 Minnesota Mining And Manufacturing Company Photothermographic element with improved adherence between layers
US5858633A (en) * 1994-12-21 1999-01-12 Eastman Kodak Company Photographic elements containing 3-alkyl group substituted 2-hydroxyphenylbenzotriazole UV absorbing polymers
US5492803A (en) * 1995-01-06 1996-02-20 Minnesota Mining And Manufacturing Company Hydrazide redox-dye-releasing compounds for photothermographic elements
US5772920A (en) * 1995-07-12 1998-06-30 Clariant Finance (Bvi) Limited U.V. absorber compositions
US5731137A (en) * 1995-08-18 1998-03-24 Fuji Photo Film Co., Ltd. Emulsified dispersion and silver halide color photographic light-sensitive material containing the same
EP0772080A2 (de) 1995-11-02 1997-05-07 Eastman Kodak Company Photographisches Element verwendbar als Kinofilm
EP0779540A1 (de) 1995-12-14 1997-06-18 Agfa-Gevaert N.V. Eine neue Klasse nicht-sensibilisierenden infrarot Farbstoffen zur Verwendung in lichtempfindlichen Elementen
US5814438A (en) * 1996-03-29 1998-09-29 Eastman Kodak Company Benzotriazole-based novel UV absorbers and photographic elements containing them
US5766834A (en) * 1996-05-17 1998-06-16 Eastman Kodak Company Photographic element containing ultraviolet absorbing polymer
EP0846571A1 (de) 1996-12-04 1998-06-10 Agfa-Gevaert N.V. Verfahren zur Herstellung eines durch Wärme erzeugten verbesserten Bildes
US6242065B1 (en) 1998-10-07 2001-06-05 Bmc Vision-Ease Lens, Inc. Lens blanks for ophthalmic elements
WO2013103139A1 (ja) 2012-01-06 2013-07-11 コニカミノルタアドバンストレイヤー株式会社 フィルムミラー、フィルムミラーの製造方法、太陽熱発電用フィルムミラー及び太陽熱発電用反射装置
US10574014B2 (en) 2017-03-27 2020-02-25 Aptiv Technologies Limited Method for sealing electric terminal assembly
US10017659B1 (en) 2017-10-09 2018-07-10 Delphi Technologies, Inc Robust sealed electric terminal assembly
EP3467051A1 (de) 2017-10-09 2019-04-10 Aptiv Technologies Limited Robuste, abgedichtete elektrische klemmenanordnung

Also Published As

Publication number Publication date
DE1166623B (de) 1964-03-26
GB1026142A (en) 1966-04-14
BE623419A (de)
JPS4429620B1 (de) 1969-12-02
FR1356243A (fr) 1964-03-27

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