US2945762A - Supersensitization of photographic emulsions using triazines - Google Patents

Supersensitization of photographic emulsions using triazines Download PDF

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US2945762A
US2945762A US540052A US54005255A US2945762A US 2945762 A US2945762 A US 2945762A US 540052 A US540052 A US 540052A US 54005255 A US54005255 A US 54005255A US 2945762 A US2945762 A US 2945762A
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series
dye
those
stilbene
triazin
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Burt H Carroll
Jean E Jones
Spence John
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to BE551712D priority Critical patent/BE551712A/xx
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Priority to US540054A priority patent/US2950196A/en
Priority to US540052A priority patent/US2945762A/en
Priority to DEE13031A priority patent/DE1054325B/de
Priority to GB30937/56A priority patent/GB852067A/en
Priority to GB30939/56A priority patent/GB852069A/en
Priority to GB2032/59A priority patent/GB852075A/en
Priority to DEE13068A priority patent/DE1057871B/de
Priority to DEE16327A priority patent/DE1081312B/de
Priority to GB34253/58A priority patent/GB852074A/en
Priority to FR9856A priority patent/FR1222414A/fr
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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
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/392—Additives
    • G03C7/39208—Organic compounds
    • G03C7/3924—Heterocyclic
    • G03C7/39244—Heterocyclic the nucleus containing only nitrogen as hetero atoms
    • G03C7/39256—Heterocyclic the nucleus containing only nitrogen as hetero atoms three nitrogen atoms
    • 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
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/08—Sensitivity-increasing substances
    • G03C1/28—Sensitivity-increasing substances together with supersensitising substances
    • 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
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
    • 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
    • Y10S264/00—Plastic and nonmetallic article shaping or treating: processes
    • Y10S264/60—Processes of molding plastisols

Definitions

  • This invention relates to photographic silver halide emulsions useful in color photography and photographic silver halide emulsions containing certain dicarbocyanine dyes, and as supersensitizers therefor, bis-tri azinylamino- It is known in the art of making photographic emulsions that certain dyes of the cyanine class alter the sensitivity of photographic emulsions of the gelatino-silverhalide kind, when the dyes are incorporated in the emulsions. It is also known that the sensitization produced by a given dye varies somewhat with the type of emulsion in which the dye is incorporated. Furthermore, the sensitization of a given emulsion by a given dyemay be altered by varying the conditions in the emulsion. For example,
  • the sensitization may be increased by increasing the silver ion concentration or decreasing the hydrogen ion concentration (i.e., increasing the alkalinity) or both.
  • sensitization can be increased by bathing plates, coated with a spectrally sensitized emulsion, in Water or in aqueous solutions of ammonia.
  • a process'of altering the sensitivity of a sensitized emulsion by increasing the silver ion concentration and/orby decreasing the hydrogen ion concentration is commonly called hypersensitization.
  • Hypersensitized emulsions have generally poor keeping qualities.
  • an object of our invention to provide photographic emulsions containing'certain dicarbocyanine dyes and, as supersensitizers therefore, bis-triazinylaminoa stilbene compounds. Another object is to provide a means for preparing these supersensitized emulsions.
  • Still another object is to provide photographic emulsions containing bis-triazinylaminostilbene compounds which are especially useful in color photography.
  • dicar-bocyanine dyes which are useful in practicing our invention can advantageously'be represented by the following general formula:
  • a heterocyclic nucleus of the benzothiazole series e.g., benzothiazole, 4-chlorobenzothiazole, S-chlorobenzothiazole, 6-chlorobenzothiazole, 7-chlorobenzothiazole, 4- methylbenzothiazole, S-methylbenzothiazole, 6-Inethylbenzothiazole, S-bromobenzothiazole, 6-bromobenzothiazole, 4-phenylbenzothiazole, S-phenylbenzothiazole, 4- methoxybenzothiazole, S-methoxybenzothiazole, 6-methoxybenzothiazole, 6-iodohenzothiazole, 5 -iodobenzotl1iazole, 4-ethoxybenz-othiazole, S-ethoxybnzothiazole, 5,6- dimethylbenzothiazole, S-hydroxybenzothiazole, 6-hydroxybenzothiazole, 6-hydroxybenzo
  • the bis-triazinylam-inostilbene compounds useful in practicing our invention have been previously employed in the 'art as fluorescent agents and as bleaching (optical) agents, and hence are widely known substances.
  • Especially useful compounds of this class comprise those compounds represented by the following general formula:
  • N N t r r thio, ethylthio,'etc. an arylthio group (e.g., 'pl1enylthio,
  • tolylthio, etc. a heterocyclylthio group (e.g.,;-benzothiazylthio, etc.), an amino group, an 'alky-lamino group (e.g., m'ethylamino, ethylamino, propylamino, dimethylamino, diethylamino, dodecylamino, cyclohexylamino, flhydroxyethylamino, A di-B-hydroxyethylamino, fi-sulfoethylarru'no, etc.),- an arylamino group (e.g.', anilino, o, m-, and p-sulfoanilino, m-, and p-chloroanilino, o-, m-, and p-anisylamino, o-, m-, and p-toludino, o-,
  • Our invention is particularly directed to the ordinarily employed gelatino-silver-halide emulsions.
  • our invention is particularly directed to the ordinarily employed gelatino-silver-halide emulsions.
  • supersensitizing combinations can be employed in; silver halide emulsions in which the carrier is other than gelatin,
  • dicarbocyanine dyes and js-triaziaylaminostilbene coated out on a suitable support, such as glass, cellulose derivative film, resin film, or paper, to a suitable thickcompounds can be employed in various concentrations depending upon the eifects desired.
  • the optimum or near optimum concentration of the dicarbocyanine dyes which we employ in practicing our invention is of the order of from 0.010 to 0.30 g. per mol. of silver halide in the emulsion.
  • our invention is directed to any silver halide emulsion containing a combination of the aforesaid dicarbocyanine dyes and s-triazinylaminostilbene compounds whereby a supersensitizing effect is obtained.
  • the s-triazinylaminostilbene compounds which we em, a ploy in our invention can advantageously be employed at I a concentration of from about 0.03 to 10.0 g. per mol. of silver halide in the emulsion.
  • a dicarbocyanine dye such as those repanine dye s-triazinylaminostilbene compound can varyv rather widely in our combinations, e.g., from 1:1 to 1:300 (by weight) in many cases.
  • the s-triazinylaminostilbene compounds can be directly. dispersed in the emulsions, or they can be dissolved in water (or an organicsolvent, such as methanol,
  • dicarbocyanine dyes can be directly dispersed in the emulsions, it is convenient to add the same in the form many of the dyes of 'Formula I. '.Mixtures of solvents, e.g., pyridine diluted with methanol or: acetone, can also be used.
  • solvents e.g., pyridine diluted with methanol or: acetone.
  • the coatings of Examples 2 to 6 were made from the same batch of gelatino-silver-bromi odide emulsion
  • the coatings of Example 1 were made from the same batch of gelatino-silverchlorobromide emulsion
  • the coatings of Example 7 were made from the same batch of gelatino-silver-chlorobromide emulsion
  • the coatings of Examples 8 and 9 were made from the same batch of gelatino-silver-bromiodide emulsion
  • the coatings of Example 10 were made from the same batch of gelatino-silver-bromiodide emulsion
  • the coatings of Examples 11 to 14 were made from the same batch of gelatino-silver-bromiodide emulsion
  • the coatings of Examples 15 and 16 were made from the same batch of gelatino-silver-bromiodide emulsion
  • the coatings of Examples 17 to 31 were made from the same batch of
  • Our invention is primarily directed to the ordinarily employed gelatino-silver-halide developing-out emulsions, e.g., gelatino-silver-chloride, -chlorobrornide, -chloroiodide, -chlorobromiodide, -bromide and -bromiodide developing-out emulsions.
  • Emulsions which form the latent image mostly inside the silver halide grains such as the emulsions set forth in U.S. Patent 2,456,956, dated Desupport, e.g., glass, cellulose nitrate film, cellulose ace-. 75
  • Photographic silver halide emulsions such as those listed above, containing the supersensitizing combinations of our invention can also containzs'uch addenda as chcmical sensiti'zers, e.g., sulfur sensitizers (e.g., allyl thio carbamide, thiour'ea, allyli'sothiocyanate, cystine, etc.), various gold compounds .(e.g., potassium chloroaurate, auric trichloride, etc.) (see U.S. Patents 2,540,085; 2,597,856 and 2,597,915), various palladium compounds, such as palladium chloride (U.S.
  • anti-foggants such as ammonium chloro- .platinateu(U.S. 2,566,245), ammonium chloroplatinite (U.S. 2,566,263), benzotriazole, nitrobenzimidazole, 5- nitroindazole, benzidine, mercaptans, etc. (see Mees The Theory of the Photographic Process, Macmillan Pub., page 460), or mixtures thereof; hardeners, such as formaldehyde (U.S. 1,763,533), chrome alum (U.S.
  • Such silver halide emulsions can also contain thiazolidones or other ultraviolet absorbing compounds, such as those described in the copending application Serial No. 419,239, filed March 29, 1954 in the name of G. W. Sawdey, now U.S. Patent 2,739,888, issued March 27, 1956. While certain emulsion addenda, such as certain ultraviolet compounds, and certain color-forming compounds cause de-sensitization or un-sensitizing efifects, it has been found that the'new combinations of our invention largely overcome such effects.
  • Typical color-form- 'Q ing compounds which can be so employed include those in U.S. Patent 2,322,027 and the following:
  • MT he results are given in' the followingtable, 5 1 v 5 Table.
  • dye' (c) (.050 :g./m0l. AgX) was incorporated in an ordinary gelatino-silver-bromiodide emulsion and together (at the-same concentration) with'compound 7 (8.0 g./mol. AgX).
  • the relative speed (red), gamma and fog are given for each of these coatings;
  • the dicarbocyanine dyes of Formula I above comprise a well known cl ass of optical sensitizing dyes. Methods for making these dyes have been previously de scribed in the prior art. See, for example, US. Patent 2,131,865, issued October 4, 1938; US. Patent 2,213,238,
  • the 3-ethyl-2-(4-meth'oxy-1,3-butadienyl) 5 phenylbenzox-azolium p-toluenesulfonate was prepared as follows.
  • the crude quaternary salt obtained by heating 99.5 g. of Z-rnethyl-5-phenylbenzoxazole and 100 g. of ethyl p-toluenesulfonate together overnight at 110 C.
  • Dye Melting point y .'229-230 C. with decomposition. e' 215-216 C. with decomposition. g" 236-237 C. with decomposition. i" 178-l80 C. with decomposition. k l77178 C. With decomposition. .me 220-221 C. with decomposition.
  • Step 1 Three solutions were-prepared as followsz (a) 260 g. of' 'purified 'diamino stilbene;'disulfonic acid 7 in 1 liter of water.
  • the antifoggant and antistain action ⁇ 2 V v (compoundQ) oi the compounds of Formula II is particularly apparent 15 silver halide or amounts in excess of 1 gram (e.g., from about 1 to grams per mole of silver halide). It has been also found that the compounds of Formula-II are, particularly useful in combination with color couplers of the water-soluble type (suchas the couplers described in US. application Serial No. 470,499, filed November 22, 1954, now U.-S.-Patent No. 2,808,329, granted Octoher 1, 1957). Such couplers when used in the absence of the compounds of Formula II cause sufliciently high fog to make their use difficult in photographic emulsions.
  • EXAMPLE 46 A photographic gelatino-silver-chlorobromide emulsion which had been optically sensitized with one of the dyes of the type represented by Formula I above and containing a coupler dispersion of a color-forming compound, such as coupler No. 5 above, was coated on a cellulose acetate film support. Separate batches of the same emulsion were prepared and to these batches were added'Calcofluor White in the amounts given below, and these emulsions were also coated on cellulose acetate film supports. Separate portions of the coatings were then exposed both before and after incubation at 120 F. for seven days,
  • EXAMPLE 50 To separate portions "of a positive "speedigelatino-silverchlorobromide emulsion was added a color couplen spch as coupler No. 5 above. "Tosome of these portions'was added an optical sensitizing .dyefas indicated in the table below, as well as'a compound bfFor'rruila The'emulsions were then coated on a conventional cellulose acetate support. Some of the emulsions were-exposed immediately after coating and drying, while some of the emulsions were exposed only'afteriincubation, as set forth in the table. Thecoat'ings incubatedfor 7days were exposed to a temperature of 120 F., 50% relative humidity,
  • 1-,cu1 ve"A represents the sensitivity'of an ordinaryge1atino-silver-bromiodide emulsion containing 3,3- diethyloxathiadicarbocyanine iodide
  • curve B represents the sensitivity ofthe same emulsion sensitized with 3,3' diethyloxathiadicarbocyanine iodide and 4,4-bis[4- i( l' sulfoanilino) -6-l3-hydroxyethylarnino-s triazin 2 ylamino] stilbene-2,2'-disulfonic acid.
  • curve C represents the sensitivityof ordinary gelatino-silver-bromiodide emulsion sensitized with 3,3-diethyloxathiadicarbocyanine iodide and 4,4f-bis(4,6- dianilino s;triazin-2 ylamino stilbene; -2,2-disulfonic acid.
  • curve D represents the sensitivity of an ordinary gelatino silver-bromiodide emulsion sensitized with 3,3"-diethylokathiadicarbocyanine iodide and 4,-'4 -bis, ('4- V phenoxy 6 8-hydroxyethylamino-s-triazin 2 -ylami no) stilbene 2',2'-disulfonic acid.
  • the sensitor'netrioj measurem'ents for the coatings of Figs; 1, 2 and 3are given in EXampI es Z; 4am 5 of Table "I above.
  • D and D each represents a s-triazin-2-yl nucleus.
  • the disulfonic acids of Formula II are generally em-- ployed in neutral aqueous solution as mentionedabove, i.e., the free acids are at least partially neutralized with;
  • n represents a group consisting of those of the benzothiazole series, those of the naphthothiazole series, those of the benzoxazole series, those of the naphthoxazole series, those of the benzoselenazole series, and those of the naphthoselenazole series
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus selected.
  • X represents an acid radical
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus selected from the group consisting of those of the benzothiazole series, those of the naphthothiazole series, those of the 'benzoxazole series, those of the naphthoxazole series, those of the benzoselenazole series, and those of the naphthoselenazole series
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus selected from the group consisting of those of the naphthothiazole series, those of the 'benzoxazole series, those of the naphthoxazole series, those of the benzoselenazole series, and those of the naphthoselenazole series
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus selected from the group consisting of those of the naphthothiazole series, those of the 'benzoxazole series, those of
  • carbocyanine dye selected from the class represented by the following general formula:
  • R and R each represents an alkyl group contamlng not more than four carbon atoms, 12 represents a positive integer of from 1 to 2, X represents an acid radical, Z represents the non-metallic atoms necessary of the benzimidazole series, and those of the 5,6-benzoquinoline series, and at least one bis(s-triazin-2-ylamino)- stilbene selected from the class represented by the following general formula:
  • D and D each represents a s-triazin-2-y1 nucleus.
  • R and R each represents an alkyl group containing from 1 to 2 carbon atoms
  • n represents a positive integer of from 1 to 2
  • X represents an acid radical
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus selected from the group consisting of those of the'benzothiazole series, those of the naphthothiazole series, those of the benzoxazole series, those of the naphthoxazole series, those of the benzoselenazole series, and those of the naphthoselenazole series
  • Z represents the nonmetallic atoms necessary to complete heterocyclic nucleus selected from the group consisting of those of the naphtothiazole series, those of the benzoxazole series, those of the naphthoxazole series, those of the benzoselenazole series, those of the naphthoselenazole series, those of the Z-quinoline series, those of the 4-quinoline series, those of the benzimidazole series
  • D and D each represents a s-tliazin-Z-yl nucleus.
  • R and R each represent an alkyl group containing from 1 to 2 carbon atoms, 11 represents a positive integer of from 1 to 2, X represents an acid radical,
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus selected from the group consisting 'of those of the benzothiazole series, those of the naphthoing of those of the naphthothiazole series, those of the benzoxazole series, those of the napthoxazole series, those to complete a heterocyclic nucleus selected from the '(Q 9; Pgnzoselcnagole series, those of the naphthoselencaster azo le series, -tho's'e of the 2 -quinoline serienthose of the 4-quinoline series, 'those ofzthe benzimidazole series, and
  • R and R each represents an alkyl group containing from 1 to 2 carbon atoms
  • X represents an acid radical
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus of the benzothiazole series and Z represents thenon-metallic atoms necessary to complete a heterocyclic nucleus of the benzoxazole series
  • D and D each represents a s-triazin-Z-yl nucleus.
  • D and D each represents a s-triazin-Z-yl nucleus.
  • R and R each represents an alkyl group containing from 1 to 2 carbon atoms
  • X represents an acid radical
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus of the benzothiazole series
  • Z represents the non-metallic.
  • D and D each represents a s-t'riazin-2-yl nucleus.
  • R and R each represents an alkyl group containing from 1 to 2 carbon atoms
  • X represents an acid radical
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus of the benzoxazole series
  • D and D each represents a s-triazin-Z-yl nucleus.
  • D and D each represents a.
  • s-triazin-Z-yl nucleus 15 A photographic gelatino-silver-halide developingout emulsion sensitized with a supersensitizing combination of 3,3-diethyloxadicarbocyanine iodide and 4,4-bis- (4-hydroxy-6-amino-s-triazin-2 -ylamino)stilbene 2,2- disulfonic acid.
  • a photographic silver emulsion capable of producing a dye image comprising a photographic silver halide emulsion containing (1) a dispersion of a color-forming compound selected from the group consisting of (a) a phenol compound capable of coupling with the oxidation products of a primary aromatic amine developing agent to provide a cyan image and (b) a pyrazolone compound capable of coupling with the oxidation products of a primary aromatic amine developing agent to provide a magenta dye image, and. (2) a bis(s-tri azin-2-ylamino)- enema by the following general formula:
  • R R R and R each represents a member selected from the group consisting of a hydrogen atom, a hydroxyl group, an aryloxyl group, an alkoxyl group, a halogen atom, a heteroeyclieradieal, an alkylthio group, an arylthio group and an amino group
  • R and R each represents a mernber selected from the group consisting of a hydrogen atom and a sulfo group, said bis- (stria zin-2-ylamino)stilbene compound being incapable of coupling with/the oxidation products of a primary aromatic amine developing agent to provide a dye image.

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  • Spectroscopy & Molecular Physics (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
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  • Plural Heterocyclic Compounds (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
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US540052A 1955-10-12 1955-10-12 Supersensitization of photographic emulsions using triazines Expired - Lifetime US2945762A (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
BE551712D BE551712A (is") 1955-10-12
US540054A US2950196A (en) 1955-10-12 1955-10-12 Supersensitization of photographic emulsions using triazines
US540052A US2945762A (en) 1955-10-12 1955-10-12 Supersensitization of photographic emulsions using triazines
DEE13031A DE1054325B (de) 1955-10-12 1956-10-02 Supersensibilisierte photographische Halogensilberemulsion
GB30939/56A GB852069A (en) 1955-10-12 1956-10-11 Improvements in dye-sensitized photographic emulsions
GB2032/59A GB852075A (en) 1955-10-12 1956-10-11 Improvements in photographic emulsions containing colour couplers
GB30937/56A GB852067A (en) 1955-10-12 1956-10-11 Improvements in dye-sensitized photographic emulsions
DEE13068A DE1057871B (de) 1955-10-12 1956-10-11 Supersensibilisierte photographische Halogensilberemulsion
DEE16327A DE1081312B (de) 1955-10-12 1956-10-11 Farbphotographische Halogensilber- emulsion
GB34253/58A GB852074A (en) 1955-10-12 1956-10-11 Improvements in photographic emulsions containing colour couplers
FR9856A FR1222414A (fr) 1955-10-12 1956-10-12 Nouvelle émulsion photographique et produits contenant une telle émulsion

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US540052A US2945762A (en) 1955-10-12 1955-10-12 Supersensitization of photographic emulsions using triazines

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Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3018287A (en) * 1958-11-05 1962-01-23 Fidelity Union Trust Company Optical brighteners for use with paper
US3132106A (en) * 1961-12-15 1964-05-05 American Cyanamid Co Brightener composition for paper derived from metanilic and sulfanilic acids
US3183231A (en) * 1963-07-17 1965-05-11 American Cyanamid Co Cyanonaphthoxazole brighteners
US3193548A (en) * 1965-07-06 Fluorescent triazinylstilbenes
US3242177A (en) * 1963-05-11 1966-03-22 Bayer Ag 7-(5-triazinyl-amino)-3-aryl-coumarin compounds
US3309363A (en) * 1964-05-11 1967-03-14 American Cyanamid Co Das triazine brightener
US3318874A (en) * 1967-05-09 Nh- hsc n n xxnh -ch -ch=ch- sosna sosna chs cha soaxchjxchsxoh
US3350395A (en) * 1963-04-12 1967-10-31 Gen Aniline & Film Corp 4, 4'-bis [(4-nu-2-sulfoethylamino)-6-sulfophenoxy-s-triazin-2-ylamino]-2, 2'-stilbenedisulfonic acid brighteners
US3401123A (en) * 1961-03-15 1968-09-10 Ncr Co Process for making case-hardened capsules and its capsule product
US3423407A (en) * 1967-10-30 1969-01-21 Gaf Corp 4,4'-bis(4,6-di(chloroanilino)-s-triazin-2-ylamino) - 2,2' - stilbenedisulfonic acid brighteners
US3459743A (en) * 1964-11-20 1969-08-05 Geigy Chem Corp Bis-triazinylaminostilbene compounds
US3479349A (en) * 1967-08-03 1969-11-18 Geigy Chem Corp Polysulfonated bis-s-triazinylamino-stilbene-2,2'-disulfonic acids
US3617295A (en) * 1967-02-23 1971-11-02 Fuji Photo Film Co Ltd Photographic silver halide emulsion
US3622339A (en) * 1967-07-07 1971-11-23 Fuji Photo Film Co Ltd Polymeric antifoggant containing at least four triazine rings
US3723425A (en) * 1970-10-13 1973-03-27 Ciba Geigy Corp Brighteners of the bis-s-triazinylaminostilbene series
US3867376A (en) * 1971-07-16 1975-02-18 Ciba Geigy Ag Bis-s-triazinyl-amino-stilbene-2,2{40 -disulphonic acids
US3895009A (en) * 1971-12-27 1975-07-15 Ciba Geigy Ag Stilbene compounds
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US8845086B2 (en) 2010-05-14 2014-09-30 Fujifilm Imaging Colorants Limited Printing process, polymer and ink
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JPS59192242A (ja) * 1983-04-15 1984-10-31 Fuji Photo Film Co Ltd ハロゲン化銀写真感光材料
JPS59218445A (ja) * 1983-05-25 1984-12-08 Fuji Photo Film Co Ltd カラ−写真感光材料
DE3783288T2 (de) 1986-08-15 1993-04-22 Fuji Photo Film Co Ltd Farbkopie und verfahren zu deren herstellung.

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US3183231A (en) * 1963-07-17 1965-05-11 American Cyanamid Co Cyanonaphthoxazole brighteners
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US3867376A (en) * 1971-07-16 1975-02-18 Ciba Geigy Ag Bis-s-triazinyl-amino-stilbene-2,2{40 -disulphonic acids
US3895009A (en) * 1971-12-27 1975-07-15 Ciba Geigy Ag Stilbene compounds
US3905964A (en) * 1972-08-04 1975-09-16 Nippon Kayaku Kk 4,4{40 -Diaminostilbene-2,2{40 -disulfonic acid derivatives and processes using same
US4138266A (en) * 1974-12-24 1979-02-06 Fuji Photo Film Co., Ltd. Method for spectrally sensitizing photographic light-sensitive emulsions
US5238793A (en) * 1988-06-06 1993-08-24 Eastman Kodak Company Photographic process
US5310907A (en) * 1990-09-11 1994-05-10 Ministero Dell`Universita` e Della Ricerca Scientifica e Tecnologica Amelinic compounds
EP0475367A1 (en) * 1990-09-11 1992-03-18 Ministero Dell' Universita' E Della Ricerca Scientifica E Tecnologica Diamino-s-triazinon derivatives and self-extinguishing polymeric compositions containing them
US6498002B2 (en) 2000-07-27 2002-12-24 Agfa-Gevaert Photographic silver halide material
US20040253182A1 (en) * 2001-10-17 2004-12-16 Mallinckrodt Inc. Pathological tissue detection and treatment employing targeted benzoindole optical agents
US7252815B2 (en) * 2001-10-17 2007-08-07 Mallinckrodt, Inc. Pathological tissue detection and treatment employing targeted benzoindole optical agents
US20090304583A1 (en) * 2001-10-17 2009-12-10 Samuel Achilefu Pathological tissue detection and treatment employing targeted benzoindole optical agents
US8845086B2 (en) 2010-05-14 2014-09-30 Fujifilm Imaging Colorants Limited Printing process, polymer and ink
US8927624B2 (en) 2010-05-14 2015-01-06 Fujifilm Imaging Colorants Limited Dispersion, process for preparing a dispersion and ink jet printing ink

Also Published As

Publication number Publication date
DE1081312B (de) 1960-05-05
DE1054325B (de) 1959-04-02
GB852069A (en) 1960-10-26
GB852075A (en) 1960-10-26
GB852074A (en) 1960-10-26
GB852067A (en) 1960-10-26
DE1057871B (de) 1959-05-21
BE551712A (is")
FR1222414A (fr) 1960-06-09

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