US3475172A - Fluorescent brightening compositions - Google Patents
Fluorescent brightening compositions Download PDFInfo
- Publication number
- US3475172A US3475172A US561012A US3475172DA US3475172A US 3475172 A US3475172 A US 3475172A US 561012 A US561012 A US 561012A US 3475172D A US3475172D A US 3475172DA US 3475172 A US3475172 A US 3475172A
- Authority
- US
- United States
- Prior art keywords
- fluorescent
- agent
- compositions
- light
- sensitive
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title description 48
- 238000005282 brightening Methods 0.000 title description 6
- 239000003795 chemical substances by application Substances 0.000 description 45
- 238000000576 coating method Methods 0.000 description 28
- 239000002904 solvent Substances 0.000 description 24
- 238000001228 spectrum Methods 0.000 description 22
- -1 monocyclic aromatic acids Chemical class 0.000 description 19
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 16
- 239000011248 coating agent Substances 0.000 description 16
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 16
- 235000021286 stilbenes Nutrition 0.000 description 16
- 150000005690 diesters Chemical class 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 14
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 14
- 230000005855 radiation Effects 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
- 108010010803 Gelatin Proteins 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- 239000007850 fluorescent dye Substances 0.000 description 9
- 239000008273 gelatin Substances 0.000 description 9
- 229920000159 gelatin Polymers 0.000 description 9
- 235000019322 gelatine Nutrition 0.000 description 9
- 235000011852 gelatine desserts Nutrition 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 8
- 229960000956 coumarin Drugs 0.000 description 7
- 235000001671 coumarin Nutrition 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 229930192474 thiophene Natural products 0.000 description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 239000000084 colloidal system Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000002950 monocyclic group Chemical group 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 6
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 5
- HPXRVTGHNJAIIH-PTQBSOBMSA-N cyclohexanol Chemical class O[13CH]1CCCCC1 HPXRVTGHNJAIIH-PTQBSOBMSA-N 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 239000000976 ink Substances 0.000 description 5
- 239000011872 intimate mixture Substances 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 239000004014 plasticizer Substances 0.000 description 5
- 230000002035 prolonged effect Effects 0.000 description 5
- 230000008901 benefit Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 230000000717 retained effect Effects 0.000 description 4
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical class OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 3
- 229960002380 dibutyl phthalate Drugs 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 206010056740 Genital discharge Diseases 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000006081 fluorescent whitening agent Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical class CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- SLYRGJDSFOCAAI-UHFFFAOYSA-N 1,3-thiazolidin-2-one Chemical class O=C1NCCS1 SLYRGJDSFOCAAI-UHFFFAOYSA-N 0.000 description 1
- ZAVJSRNWXMIYMC-UHFFFAOYSA-N 1-chloro-6-dodecylcyclohexa-2,4-dien-1-ol Chemical compound C(CCCCCCCCCCC)C1C(C=CC=C1)(O)Cl ZAVJSRNWXMIYMC-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- RSZXXBTXZJGELH-UHFFFAOYSA-N 2,3,4-tri(propan-2-yl)naphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(C(C)C)C(C(C)C)=C(C(C)C)C(S(O)(=O)=O)=C21 RSZXXBTXZJGELH-UHFFFAOYSA-N 0.000 description 1
- INLGLGPJBNIIHG-UHFFFAOYSA-N 2-[4-[2-[4-[5,7-bis(2-methylbutan-2-yl)-1,3-benzoxazol-2-yl]phenyl]ethenyl]phenyl]-5,7-bis(2-methylbutan-2-yl)-1,3-benzoxazole Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=C2OC(C3=CC=C(C=C3)C=CC3=CC=C(C=C3)C=3OC4=C(C=C(C=C4N=3)C(C)(C)CC)C(C)(C)CC)=NC2=C1 INLGLGPJBNIIHG-UHFFFAOYSA-N 0.000 description 1
- UMTUDVFXSSAPGG-UHFFFAOYSA-N 2-butyl-1,3-benzoxazole Chemical compound C1=CC=C2OC(CCCC)=NC2=C1 UMTUDVFXSSAPGG-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N 4-methylcyclohexan-1-ol Chemical compound CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- XFBISLQOZQFNDE-UHFFFAOYSA-N 4-tert-butyl-2-[5-(4-tert-butyl-1,3-benzoxazol-2-yl)thiophen-2-yl]-1,3-benzoxazole Chemical compound C1=CC=C2OC(C3=CC=C(S3)C=3OC=4C=CC=C(C=4N=3)C(C)(C)C)=NC2=C1C(C)(C)C XFBISLQOZQFNDE-UHFFFAOYSA-N 0.000 description 1
- AIXZBGVLNVRQSS-UHFFFAOYSA-N 5-tert-butyl-2-[5-(5-tert-butyl-1,3-benzoxazol-2-yl)thiophen-2-yl]-1,3-benzoxazole Chemical group CC(C)(C)C1=CC=C2OC(C3=CC=C(S3)C=3OC4=CC=C(C=C4N=3)C(C)(C)C)=NC2=C1 AIXZBGVLNVRQSS-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 206010011878 Deafness Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CWNSVVHTTQBGQB-UHFFFAOYSA-N N,N-Diethyldodecanamide Chemical compound CCCCCCCCCCCC(=O)N(CC)CC CWNSVVHTTQBGQB-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- JQBFLQHPLBHJNS-UHFFFAOYSA-N amino cyanoformate Chemical compound NOC(=O)C#N JQBFLQHPLBHJNS-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical class OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- RLWYOEZLEULOLU-UHFFFAOYSA-M sodium;2,3,4-tri(propan-2-yl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=CC2=C(C(C)C)C(C(C)C)=C(C(C)C)C(S([O-])(=O)=O)=C21 RLWYOEZLEULOLU-UHFFFAOYSA-M 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
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, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials 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)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB27888/65A GB1122643A (en) | 1965-07-01 | 1965-07-01 | Photographic print materials |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3475172A true US3475172A (en) | 1969-10-28 |
Family
ID=10266906
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US561012A Expired - Lifetime US3475172A (en) | 1965-07-01 | 1966-06-28 | Fluorescent brightening compositions |
Country Status (4)
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3900608A (en) * | 1971-10-23 | 1975-08-19 | Bayer Ag | Preparations of optical brighteners |
| US4684606A (en) * | 1985-12-24 | 1987-08-04 | Eastman Kodak Company | Sterically hindered photographic coupler solvents and photographic elements employing same |
| EP0306447A1 (de) * | 1987-08-26 | 1989-03-08 | Ciba-Geigy Ag | Dispersionsaufheller-Präparate |
| US4827019A (en) * | 1985-12-24 | 1989-05-02 | Eastman Kodak Company | Sterically hindered aromatic carboxylic esters |
| US4921781A (en) * | 1987-09-18 | 1990-05-01 | Konica Corporation | Silver halide photographic material |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3125536A (en) * | 1964-03-17 | Vinyl products and process | ||
| US3185650A (en) * | 1962-01-23 | 1965-05-25 | Dow Chemical Co | Phosphor-dielectric composition |
-
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 DE DE19661547709 patent/DE1547709A1/de active Pending
- 1966-06-28 US US561012A patent/US3475172A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3125536A (en) * | 1964-03-17 | Vinyl products and process | ||
| US3185650A (en) * | 1962-01-23 | 1965-05-25 | Dow Chemical Co | Phosphor-dielectric composition |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3900608A (en) * | 1971-10-23 | 1975-08-19 | Bayer Ag | Preparations of optical brighteners |
| US4684606A (en) * | 1985-12-24 | 1987-08-04 | Eastman Kodak Company | Sterically hindered photographic coupler solvents and photographic elements employing same |
| EP0228064A3 (en) * | 1985-12-24 | 1988-01-13 | Eastman Kodak Company | Photographic elements with sterically hindered photographic coupler solvents |
| US4827019A (en) * | 1985-12-24 | 1989-05-02 | Eastman Kodak Company | Sterically hindered aromatic carboxylic esters |
| EP0306447A1 (de) * | 1987-08-26 | 1989-03-08 | Ciba-Geigy Ag | Dispersionsaufheller-Präparate |
| US5064570A (en) * | 1987-08-26 | 1991-11-12 | Ciba-Geigy Corporation | Dispersion fluorescent brightener preparations |
| US4921781A (en) * | 1987-09-18 | 1990-05-01 | Konica Corporation | Silver halide photographic material |
Also Published As
| Publication number | Publication date |
|---|---|
| BE683218A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1966-12-01 |
| GB1122643A (en) | 1968-08-07 |
| DE1547709A1 (de) | 1971-11-25 |
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