Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
  • C09D5/22—Luminous paints
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
  • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
• • 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
  • G03C1/815—Photosensitive materials characterised by the base or auxiliary layers characterised by means for filtering or absorbing ultraviolet light, e.g. optical bleaching
  • G03C1/8155—Organic compounds therefor

Definitions

• Fluorescent compositions comprising an intimate mixture of (l) at least one Water-soluble fluorescent agent .which-has strong absorption of radiation in the ultraviolet
• This invention relates to fluorescent compositions for incorporation in compositions of matter and more particularly to fluorescent agent-solvent compositions and to photographic light-sensitive"elements containing these -fluores'c'ent compositions.
• the whiteness in monochrome and color photographic prints may be enhanced by various methods which have been proposed from time to time.
• the prints may be bathed in a solution of a fluorescent whitening agent before drying, but such treatment may be suflicient to enhance the whiteness in the low density areas of the print and tends to cause a bloom in the high density areas of the prints.
• a fluorescent whitening agent beneath the light-sensitive layers of monochrome or color light-sensitive material.
• Another object of our invention is to provide photographic light-sensitive elements which have at least one novel layer containing a hydrophilic colloid having dispersed therein an intimate mixture of (1) a fluorescent agent which has strong absorption of radiation in the ultraviolet region of the spectrum, high fluorescent emission in the blue region of the spectrum and whichis substantially insoluble in Water, and (2) a solvent dispersing agent for the fluorescent agent. Still other objects will become apparent from a consideration of the following specification and claims.
• novel fluorescent compositions which in their simplest form comprise an intimate mixture of:
• a fluorescent agent which has strong absorption of radiation in the ultraviolet region of the spectrum, high fluorescent emission in the blue region of the spectrum and which is substantially insoluble in water, and
• Our fluorescent compositions also advantageously contain combinations of fluorescing agents and/ or combinations of diesters'derived from dibasic monocyclic aromatic acids and alkyl-substituted cyclohexanols.
• Our fluorescent compositions provide strong fluorescence and have substantially improved fluorescent stability to prolonged exposure to light as compared to fluorescent compositions known before.
• Our fluorescent compositions are used to advantage for incorporation in various compositions and matter where fluorescence is desired such as in fluorescent paints, inks, plasticizers, and in particular, in light-sensitive photographic materials where itis desired to increase the whiteness of the highlight areas in either black-and-white prints or in color prints.
• Typical examples of diesters of Formula I include the following:
• fluorescent agent which absorbs radiation in the ultraviolet region of the spectrum, having high fluorescent emission in the blue region of the spectrum and .which is substantially insoluble in water is advantageously used according to our invention.
• useful fluorescent agents includes stilbene, coumarin and thiophene fluorescent agents. Among such fluorescent agents are the following:
• R R R R and R are aryl, alkyl, alkoxy, aryloxy, hydroxyl, amino, cyano, carboxylic acid, amide, ester, alkyl carbonyl, alkylsulfo or diallrylsulfonyl radicals, or hydrogen atoms;
• R; and R can be hydrogen atoms, alkyl radicals such as methyl, ethyl, etc., or cyano radicals.
• our fluorescent agents are used in our fluorescent compositions over a wide range of concentrations,the optimum concentration being readily determined for a given agent and photographic element by methods well known in the art.
• the optimum concentration depends upon a number of factors including the particular fluorescent agent, the particular photographic element, and the results desired; however, usually enough fluorescent agent is used so that when it is coated, the fluorescent agent will be coated in the range of from about 1 mg. to about mg. per square foot, preferably in the range from about 5 mg. to about 35 mg. per square foot.
• Enough dispersing solvent i.e., a diester of a mono cyclic aromatic acid and an alkyl substituted cyclohexanol is used in our fluorescent composition to dissolve the fluorescent agent.
• An excess of solvent may be used, if desired, however, usually only a small excess is used.
• the optimum amount of solvent used for a given amount of fluorescent agent will depend upon the particular fluorescent agent and solvent used and is readily determined by methods well known in the art.
• amylphenyl)-naphthamide S-hydroxy-lea-naphthoyl-1,2,3,4-tetrahydroquinoline 2-lauryl-1-chlorophenol 1-naphthol-2-carboxylic-a-naphthalide lfrnaphthol-S-sulfO-cyclohexylamide 5phenoxyacetamino-1-naphthol SAp-phenyIprQ iQnylamino-1-naphthol Monochlor-S (N-y-phenylpropyl-N-p-sec.
• the fluorescent coating compositions A, B and C were each coated-.onnon-fluorescent paper (over a geIatin pad of 6 ml. of 10% gelatin per sq. ft.).. at 10 mlpdispersio'n per sq. ft. l 1.
• EXAMPLE 5 8 m1. of 10% gelatin per sq. ft.) at 10 mll of dispersion per sq. ft. as Coatings D, E, F and G, respectively.
• Example 10 4,4'-di-(5,7-di-t-pentylbenzoxazol-2-yl)stilbene was dissolved in various solvents at a concentration of 3 mg. per liter (4x10- molar). These solutions were faded in bulk by exposure to U.V. radiation of wavelength 365 mg. The fluorescent emission was measured from time to time by means of a photocell and photomultiplier. The percent emission compared with the initial emission-is 4,4'-di-(5,7-di-t-pentylbenzoxazol 2 yl)stilbene (0.05 35 giveninTable 4.
• EXAMPLE 6 A dispersion was prepared as in Example 5 except that di-(x-methylcyclohexyl)isophthalate (where x denotes a mixture of 2, 3 and 4-methyl substituted cyclohexyl) was used in place of di-2-methylcyclohexyl isophthalate.
• EXAMPLE 8 The results show that "there was no decrease in the fluorescent emission for the fluorescent composition having di-(Z-methyl-cyclohexyl)terephthalate as the solvent following 6 hours of exposure to U .V. radiation while the fluorescent compositions containing di-butyl phthalate, tricresyl phosphate, cyclohexane-1,4-dimethanoldiformate and cyclohexanol, respectively, as the solvent produced only 80.8%, 81.0%, 869% and 88.0%, respectively, of their initial fluorescent emission following 5 hours exposure to the ultraviolet radiation. These results demonstrate the technical advance provided by use .of our fluorescent compositions.
• fluorescent compositions of. our invention are used to advantage for incorporationin photographic elements to increase the whiteness of the highlights in either. blackand-white print material or color print material: and have utility also as fluorescing material in fluorescent paints, inks, plasticizers,-etc.
• Our fluorescent compositions are characterized by having strong fluorescent emission initially as well as showing significantly improved fluores cent stability upon prolonged exposure to ultraviolet light. 1 I
• a fluorescent composition having improved stability to prolonged exposure to light comprising an intimate mixture of:
• R and R each represent an alkyl group and R R R and R each represent a member selected from the class consisting of a hydrogen atom and an alkyl radical.
• a composition of claim 1 dispersed in a film-forming hydrophilic colloid.
• a fluorescent agent which has a strong absorption of radiation in the ultra-violet region of the spectrum, high fluorescent emission in the blue region of the spectrum, and which is substantially insoluble in water and (2) a diester derived from a dibasic monocyclic aromatic acid and an alkyl-substituted cyclohexanol as a dispersing solvent for said fluorescent agent.
• a photographic element of claim 7 in which the fluorescent agent is selected from the group consisting of a thiophene fluorescent agent, a stilbene fluorescent agent and a coumarin fluorescent agent and in which the said fluorescent agent is dissolved in the said diester.
• R and R each represent an alkyl group
• R R R and R 13 each represent a member selected from the class consisting of a hydrogen atom and an alkyl radical
• the said diester is a solvent for the said fluorescent agent
• a photographic element comprising a support having a white surface, a plurality of coatings over said white surface, which coatings include light-sensitive coatings, one coating being sensitive to the blue region of the spectrum, another being sensitive to the green region of the spectrum and another being sensitive to the red region of the spectrum, the red-sensitive coating being the outermost coating, said red-sensitive coating containing a dispersion of a solution of:
• a fluorescent agent which has a strong absorption of radiation in the ultraviolet region of the spectrum, high fluorescent emission in the blue region of the spectrum and which is substantially insoluble in water, and
• a photographic element comprising a support with a white surface and a plurality of coatings therein including one light-sensitive coating sensitive to blue light, another light-sensitive coating sensitive to green light and another light-sensitive coating sensitive to red light, the red light-sensitive coating being the outermost lightsensitive coating, the improvement for brightening white areas of a print made from said element which comprises incorporating in the said red-sensitive coating a dispersed solution of (1) a fluorescent agent which has a strong absorption of radiation in the ultraviolet region of the spectrum, high fluorescent emission in the blue region of the spectrum and which is substantially insoluble in water, and
• a photographic element comprising a support with a white surface and at least one light-sensitive silver halide emulsion layer, the improvement for brightening White areas of a print made from said element which comprises incorporating in at least one layer of the said element a dispersed solution of:
• a fluorescent agent which has a strong absorption of radiation in the ultraviolet region of the spectrum, high fluorescent emission in the blue region of the spectrum, and which is substantially insoluble in water, and

Landscapes

• Chemical & Material Sciences (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Organic Chemistry (AREA)
• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Life Sciences & Earth Sciences (AREA)
• Wood Science & Technology (AREA)
• Inks, Pencil-Leads, Or Crayons (AREA)
• Luminescent Compositions (AREA)
• Silver Salt Photography Or Processing Solution Therefor (AREA)

Applications Claiming Priority (1)

Publications (1)

Family

ID=10266906

Family Applications (1)

Country Status (4)

Cited By (5)

Citations (2)

• 1965
  • 1965-07-01 GB GB27888/65A patent/GB1122643A/en not_active Expired
• 1966
  • 1966-06-27 BE BE683218D patent/BE683218A/xx unknown
  • 1966-06-28 US US561012A patent/US3475172A/en not_active Expired - Lifetime
  • 1966-06-28 DE DE19661547709 patent/DE1547709A1/de active Pending

Patent Citations (2)

Also Published As

Similar Documents