US2639990A - Process for improving the whiteness or color of materials and products resulting therefrom - Google Patents

Process for improving the whiteness or color of materials and products resulting therefrom Download PDF

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Publication number
US2639990A
US2639990A US165116A US16511650A US2639990A US 2639990 A US2639990 A US 2639990A US 165116 A US165116 A US 165116A US 16511650 A US16511650 A US 16511650A US 2639990 A US2639990 A US 2639990A
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Prior art keywords
phenyl
materials
alkyl
class consisting
compounds
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US165116A
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English (en)
Inventor
Kendall John David
Duffin George Frank
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Ilford Imaging UK Ltd
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Ilford Ltd
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
    • D01D10/00—Physical treatment of artificial filaments or the like during manufacture, i.e. during a continuous production process before the filaments have been collected
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F1/00—General methods for the manufacture of artificial filaments or the like
    • D01F1/02—Addition of substances to the spinning solution or to the melt
    • D01F1/10—Other agents for modifying properties
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/60—Optical bleaching or brightening
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/35—Heterocyclic compounds
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/30—Luminescent or fluorescent substances, e.g. for optical bleaching
    • 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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M8/00—Fuel cells; Manufacture thereof
    • H01M8/04—Auxiliary arrangements, e.g. for control of pressure or for circulation of fluids
    • H01M8/04276—Arrangements for managing the electrolyte stream, e.g. heat exchange
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/30—Hydrogen technology
    • Y02E60/50—Fuel cells

Definitions

  • the foregoing definition of the compounds does not include compounds in which R1 or Arc 5 dfersfitlood tetxtlle materials generally, 1n till: ntains a mtro substltuent, or 1n which An cong g mgg g gg z' z ifi gg 3 g z tains a sulphonic carboxylic nitro or cyano group Y since those compounds do not fluoresce.
  • the free carboxylic and sulphonic acids gi i fi g iud d pogntiers 1 fib l m;- are substantive to protein and polyamlde fibres teriais sllch 22 1 g d g g gfi i z and films, but for the other materials, e. g. cellu losic materials such as cotton and paper, an $2135 :zmgg zf z i gf i ggfi i gi %gg cellulose acetate materials, the alkali salts are generally preferred. arias 221:3212?marria es: 5"?
  • M.P.,C from compacted fibres, e. g. paper, cardboard, 25 l g- %p y l ps ra e felt and the like, or from natural colloids such j f l f f gggggfgg as gelatin.
  • a process 1:5-6 phenyl-3-p-eth0xyphenyl pyraz011ne 13% for improving fibres and films comprises applyiz2 itfifitiiii?t ititiiit fitlh ttittie::::::: its ing thereto a small quantity Of a.
  • R1 is a' 'hydroge'n'atom, hydrocarbon kfigiifilg fifigfifififig1it?t;onn roup or substitutedhydrocarbon group,
  • phenyl or naphthyl I p su1ph0phenyl 31,401yl 5 phem,lpymzoline which may contain any of the substituents hyl-psulgfiopgenyl-gg-nigthoiiylphfliylgihleiiyl pg-lz'ilziollne n-p-su op eny- -e oxy eny -o-p e y pyr ne droxy F hydFoxya'lkyl' p hydrocar' 1 -sulphophenyl-3-p-phenoxyphenyl-5-phenyl pyrazoline bon-substituted-ammo or acylammo groups or 1-p-Su%pg0plfienyl-g-(g-phingl)phiiilyl iplhenyil pyrazolline .-p-su p o
  • WhlOh compound is colourless in aqueous i inetliyll-os ulghgflillienylg 59 111 11 fiiyralzolme 1,
  • T 2 1-(4 8-disulphonaphthyl-2l-3 5-diphenyl pyrazoline less in aqueous or ethyl alcoholic solution
  • 1s 5
  • p-sulphophen yl-3pl1enyl-5-a-furylpyrazohne meant that a solution of the compound in water 5 1 Pymzohne or ethyl alcohol has an absorption maximum not greater than 4000' A.
  • the preferred compounds according to the" present invention are those in which the pyrazoline contains a sulphophenyl group in the 1-posi tion and contains in the 3- and 5-positions phenyl groups or substituted phenyl groups.
  • the compounds may be prepared by various methods.
  • One method is described in co-pending application Serial No. 165,118, filed on even date herewith.
  • A. second method consists in the condensation of a Mannich reaction product (ob tained from an acetophenone with formaldehyde and an amine) with an aryl hydrazine
  • the whiteness of textile materials, paper and the like can be very considerably enhanced by treating the materials with a solution of one of the said compoundsin water or an organic solvent, e. g. at a solution concentra tion of 1 part in 5000 to 1 part in 100,000.
  • the compound in which R1 or Arz contains a sulphonic acid group may be used from weakly acid solution or even neutral solution and are substantive to wool from such solutions.
  • the 10 partsjof bath will contain 0.0001 part of fiuorescer, i. e.,- one part of fibre takes up 0.0001 part of fluorescer. which is 0.01%. Therefore from the figures of l to 5,000 and. 1 to 100,000
  • the compounds of this invention may be applied thereto at any stage in the manufacture of such materials.
  • the compounds of this invention may be incorporated in such compositions before extrusion or casting so that they are uniformly dispersed throughout the products.
  • the preferred fibres or films may be treated with solutions of the compounds.
  • the compounds may be included in any of the liquids commonly employed for dyeing, scouring, dressing and the like, and this invention includes compositions for application to textiles for such purposes which include a compound of the" foregoing formula. in conjunction with a textile dye,
  • the compounds may be applied to the materials after the normal processes of their manufacture have been completed, for example by including the compounds in domestic washing preparations.
  • the compounds may be applied to the wood pulp or rag-fibre before such material is made into paper, or during the paper-making operation, or may be applied as a solution directly to the raw paper, or may be applied in a dressing composition, e. 'g. a baryta coating, applied to the paper.
  • a dressing composition e. 'g. a baryta coating
  • One important application of the invention is in the treatment of photographic prints'where application of a solution of a compound of the foregoing general formula has the effect of whitening the highlights of the print.
  • Considerable effort has hitherto been directed to the produc--- tion of prints having brilliant highlights, and the present invention provides a simple method whereby this result may be achieved.
  • the compounds may, if desired, be incorporated in the photographic emulsions, or sub-coat or supercoat layers, prior to coating such layers to form the photographic element.
  • the tone may be changed to resemble very closely the cold tone commonly associated with prints made on paper coated with silver chloride emulsions.
  • the compounds of this invention may also be applied to films coated on supports, for example to finished photographic films or plates where the gelatin film takes up the compound and is photographic thereby caused to fluoresce and the image to appear colder in tone.
  • a process 'for improving fibres and films which comprises applying thereto a dispersion in a liquid medium of a white fluorescent compound of the general formula:
  • R1 is selected from the class consisting of the hydrogen atom, alkyl, unsubstituted phenyl and phenyl containing alkyl, alkoxy, chloro and sulphonic substituents
  • Ari is selected from the class consisting of unsubstituted phenyl and phenyl containing halogen, alkyl, alkoxy and phenoxy substituents
  • Ara is selected from the class consisting of unsubstituted phenyl and phenyl containing halogen, alkyl, sulphonic and acetylamino substituents, so that the said fibres and films absorb 0.01 to 1% by weight of the said compound.
  • a process for improving fibres and films which comprises applying thereto an aqueous solution of a white fluorescent compound of the general formula:
  • R1 is selected from the class consisting of the hydrogen atom, alkyl, unsubstituted phenyl and phenyl containing alkyl, alkoxy, chloro and sulphonic substituents
  • Ari is selected from the class consisting of unsubstituted phenyl and phenyl containing halogen, alkyl, alkoxy and phenoxy substituents
  • M2 is selected from the class consisting of unsubstituted phenyl and phenyl containing halogen, alkyl, sulphonic and acetylamino substituents, so that the said fibres and films absorb 0.01 to 1% by weight of the said compound.
  • a process for improving fibres and films which comprises applying thereto an aqueous solution of a fluorescent compound of the general formula:
  • R1 is selectedfrom the class consisting of the hydrogen atom, alkyl, unsubstituted 61' phenyl and phenyl containing alkyl, alkoxy, chloro and sulphonic substituents
  • ,Ar1 is selected from the class consisting of. unsubstituted phenyl and phenyl containing halogen, alkyl, alkoxy 1 and phenoxy substituents
  • A12 is selected from the class consisting of unsubstituted phenyl and phenyl containing halogen, alkyl,-sulphonic and acetylamino substituents, so that the said fibres and films absorb 0.01 to 1% by'weight of the said compound.
  • a process for improving the whiteness of wool fibres and woollen textile materials which comprises applying thereto an aqueous solution of a compound of the general formula:
  • R1 is a sulphonated phenyl group
  • An is selected from the class consisting of unsubstituted phenyl and phenyl containing halogen, alkyl, alkoxy and phenoxy substituents, and
  • Arz is selected from the class consisting of unsubstituted phenyl and phenyl containing halogen, alkyl, sulphonic and acetylamino substituents, so that the said fibres and films absorb 0.01 to 1% by weight of the said compound.
  • R1 is selected from the class consisting of the hydrogen atom, alkyl, unsubstituted phenyl and phenyl containing alkyl, alkoxy, chloro and sulphonic substituents
  • Ari is selected from the class consisting of unsubstituted phenyl and phenyl containing halogen, alkyl, alkoxy and phenoxy substituents
  • An is selected from the class, consisting of unsubstituted phenyl and phenyl containing halogen, alkyl, sulphonic andacetylamino substituents.
  • Photographic light-sensitive materials having adsorbed thereto 0.01 to 1% by weight of a fluorescent compound of the general formula:
  • R1 is selected from the classconsisting of the hydrogen atom, alkyl, unsubstituted phenyl and phenyl containing alkyl, alkoxy, chloro and sulphonic substituents, AT]. is selected from the class consisting of unsubstituted phenyl and phenyl containing halogen, alkyl, alkoxy and phenoxy substituents, and 'Alz is selected from the class consisting of unsubstituted phenyl and phenyl containing halogen, alkyl, sulphonic and acetylamino substituents.
  • Photographic printing paper having adsorbed thereto 0.01 to 1% by weight of a compound of the general formula:
  • R1 is selected from the class consisting of the hydrogen atom, alkyl, unsubstituted phenyl and phenyl containing alkyl, alkoxy, chloro and sulphonic substituents
  • Ari is selected from the class consisting of unsubstituted phenyl and phenyl containing halogen, alkyl, alkoxy and phenoxy substituents
  • Arz is selected from. the class consisting of unsubstituted phenyl and,
  • R1 is selected from the class consisting of the hydrogen atom, alkyl, unsubstituted phenyl and phenyl containing alkyl, alkoxy, chloro and sulphonic substituents
  • Ari is selected from the class consisting of unsubstituted phenyl and phenyl containing halogen, alkyl, alkoxy and phenoxy substituents
  • Ar: i selected from the class consisting of unsubstituted phenyl and phenyl containing halogen, alkyl, sulphonic and' acetylamino substituents, so that the said fibres 8 and films absorb 0.01 to 1% by weighto! the said compound.
  • a process for improving fibres and, films which comprises applying thereto a dispersion in a liquid medium of a white fluorescent compound of the general formula:
  • R1 is selected from the class consisting of the hydrogen atom, methyl, phenyl, methylphenyl, methoxyphenyl, chlorophenyl and sulphophenyl groups
  • X1 represents at least one substituent group selected from the class consisting of hydrogen, halogen, methyl, methoxy, ethoxy and phenoxy
  • X2 represents at least one substituent group selected from the class consisting of hydrogen, halogen, methyl, sulphonic and acetylamino groups, so that the said fibres and films absorb 0.01 to 1% by weight of the said compound.
  • R1 is selected from the class consisting of the hydrogen atom, methyl, phenyl, methylphenyl, methoxyphenyl, chlorophenyl and sulphophenyl groups
  • X1 represents at least one substituent group selected from the class consisting of hydrogen, halogen, methyl, methoxy, ethoxy and phenoxy
  • X2 represents at least one substituent group selected from the class consisting of hydrogen, halogen, methyl, sulphonic and acetylamino groups.

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  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Textile Engineering (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Manufacturing & Machinery (AREA)
  • General Chemical & Material Sciences (AREA)
  • Electrochemistry (AREA)
  • Sustainable Energy (AREA)
  • Sustainable Development (AREA)
  • Mechanical Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Coloring (AREA)
  • Artificial Filaments (AREA)
  • Paper (AREA)
US165116A 1949-06-03 1950-05-29 Process for improving the whiteness or color of materials and products resulting therefrom Expired - Lifetime US2639990A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB15009/49A GB669590A (en) 1949-06-03 1949-06-03 Improvements in or relating to a process for improving the whiteness of colour materials

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US (1) US2639990A (xx)
CH (2) CH288169A (xx)
DE (1) DE966411C (xx)
FR (1) FR1021379A (xx)
GB (1) GB669590A (xx)
NL (1) NL79254C (xx)

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2785133A (en) * 1954-03-26 1957-03-12 Gen Aniline & Film Corp Compositions for a method of whitening fine fabrics
US2837485A (en) * 1958-06-03 Ari-ch
US2938292A (en) * 1955-08-18 1960-05-31 Ultra Violet Products Inc Fingerprinting system
US2983604A (en) * 1955-11-03 1961-05-09 Gen Aniline & Film Corp Quenching solution for fluorescent photographic paper employed in the manufacture ofhalftone negatives
US2985593A (en) * 1958-09-26 1961-05-23 Borden Co Scintillator composition
US3127266A (en) * 1958-08-09 1964-03-31 Chzxn
US3131079A (en) * 1960-08-12 1964-04-28 Bayer Ag Brightening of fiber material by coating with 1, 3-diaryl- and 1, 3, 5-triaryl pyrazoline derivatives
US3133080A (en) * 1964-05-12 Optical whitening agents of the
US3141879A (en) * 1964-07-21 Chj-chz
US3181949A (en) * 1958-06-02 1965-05-04 Gevaert Photo Prod Nv Light sensitive elements having optical bleaching compositions coated thereon
US3181948A (en) * 1958-06-02 1965-05-04 Gevaert Photo Prod Nv Method for optical bleaching of coated papers and resultant product
US3181950A (en) * 1957-06-06 1965-05-04 Gevaert Photo Prod Nv Method for optical bleaching of coated photosensitive papers and resultant product
US3257204A (en) * 1958-08-22 1966-06-21 Azoplate Corp Electrophotographic reproduction material
US3257203A (en) * 1958-08-20 1966-06-21 Azoplate Corp Electrophotographic reproduction material
US3378389A (en) * 1962-03-31 1968-04-16 Bayer Ag 1, 3-diphenyl pyrazolines and method for brightening synthetic material therewith
US3434837A (en) * 1964-06-05 1969-03-25 Eastman Kodak Co Photographic element
US3447943A (en) * 1964-09-02 1969-06-03 Ici Ltd Process for the whitening of polymeric materials
US3498791A (en) * 1965-10-27 1970-03-03 Keuffel & Esser Co Two-component diazotype material
US3755352A (en) * 1966-12-23 1973-08-28 Ciba Geigy Corp 1-(4{40 -methoxysulphonyl-phenyl)-3-(4{41 -chlorophenyl)-pyrazoline
US3754964A (en) * 1971-02-26 1973-08-28 Ciba Geigy Corp Process for the continuous optical brightening of acylated cellulose fibre material
US4595458A (en) * 1985-05-17 1986-06-17 Olin Corporation Process for using selected fatty acid adducts of a 1,2,4-triazole as sizing or waterproofing agents for cellulosic materials
US5208251A (en) * 1986-05-09 1993-05-04 Warner-Lambert Company Styryl pyrazoles, isoxazoles and analogs thereof having activity as 5-lipoxygenase inhibitors, pharmaceutical compositions and methods of use therefor
EP0915370A1 (en) * 1997-11-04 1999-05-12 Konica Corporation Silver halide light-sensitive photographic material

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1104483B (de) * 1955-10-10 1961-04-13 Bayer Ag Aufhellungsmittel
DE1157193B (de) * 1957-10-30 1963-11-14 Unilever Nv Aufhellen von Textilien
DE1419329B1 (de) * 1962-04-21 1970-01-15 Hoechst Ag 1,3-Diaryl-delta-pyrazolinverbindungen und ihre Verwendung als Aufhellungsmittel
DE1469222B1 (de) * 1964-09-25 1972-03-09 Hoechst Ag Pyrazolinderivate sowie ihre Herstellung und Verwendung

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2153615A (en) * 1936-10-23 1939-04-11 Du Pont 1-aryl-5-pyrazolone-3-carboxylic acids
GB566810A (en) * 1943-05-20 1945-01-15 Unilever Ltd Method of and preparations for improving the whiteness of materials

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR878823A (fr) * 1941-02-18 1943-02-04 Ig Farbenindustrie Ag Procédé permettant d'accentuer les blancs et le pouvoir lumineux de la couleur de la surface des images photographiques
DE735478C (de) * 1941-07-12 1943-05-18 Ig Farbenindustrie Ag Verfahren zur Herstellung von 4, 5-Diarylimidazolinabkoemmlingen
GB584435A (en) * 1944-03-01 1947-01-15 Unilever Ltd Improvements in the laundering of white textile articles

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2153615A (en) * 1936-10-23 1939-04-11 Du Pont 1-aryl-5-pyrazolone-3-carboxylic acids
GB566810A (en) * 1943-05-20 1945-01-15 Unilever Ltd Method of and preparations for improving the whiteness of materials

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2837485A (en) * 1958-06-03 Ari-ch
US3133080A (en) * 1964-05-12 Optical whitening agents of the
US3141879A (en) * 1964-07-21 Chj-chz
US2785133A (en) * 1954-03-26 1957-03-12 Gen Aniline & Film Corp Compositions for a method of whitening fine fabrics
US2938292A (en) * 1955-08-18 1960-05-31 Ultra Violet Products Inc Fingerprinting system
US2983604A (en) * 1955-11-03 1961-05-09 Gen Aniline & Film Corp Quenching solution for fluorescent photographic paper employed in the manufacture ofhalftone negatives
US3181950A (en) * 1957-06-06 1965-05-04 Gevaert Photo Prod Nv Method for optical bleaching of coated photosensitive papers and resultant product
US3181949A (en) * 1958-06-02 1965-05-04 Gevaert Photo Prod Nv Light sensitive elements having optical bleaching compositions coated thereon
US3181948A (en) * 1958-06-02 1965-05-04 Gevaert Photo Prod Nv Method for optical bleaching of coated papers and resultant product
US3127266A (en) * 1958-08-09 1964-03-31 Chzxn
US3257203A (en) * 1958-08-20 1966-06-21 Azoplate Corp Electrophotographic reproduction material
US3257204A (en) * 1958-08-22 1966-06-21 Azoplate Corp Electrophotographic reproduction material
US2985593A (en) * 1958-09-26 1961-05-23 Borden Co Scintillator composition
US3131079A (en) * 1960-08-12 1964-04-28 Bayer Ag Brightening of fiber material by coating with 1, 3-diaryl- and 1, 3, 5-triaryl pyrazoline derivatives
US3378389A (en) * 1962-03-31 1968-04-16 Bayer Ag 1, 3-diphenyl pyrazolines and method for brightening synthetic material therewith
US3434837A (en) * 1964-06-05 1969-03-25 Eastman Kodak Co Photographic element
US3447943A (en) * 1964-09-02 1969-06-03 Ici Ltd Process for the whitening of polymeric materials
US3498791A (en) * 1965-10-27 1970-03-03 Keuffel & Esser Co Two-component diazotype material
US3755352A (en) * 1966-12-23 1973-08-28 Ciba Geigy Corp 1-(4{40 -methoxysulphonyl-phenyl)-3-(4{41 -chlorophenyl)-pyrazoline
US3754964A (en) * 1971-02-26 1973-08-28 Ciba Geigy Corp Process for the continuous optical brightening of acylated cellulose fibre material
US4595458A (en) * 1985-05-17 1986-06-17 Olin Corporation Process for using selected fatty acid adducts of a 1,2,4-triazole as sizing or waterproofing agents for cellulosic materials
US5208251A (en) * 1986-05-09 1993-05-04 Warner-Lambert Company Styryl pyrazoles, isoxazoles and analogs thereof having activity as 5-lipoxygenase inhibitors, pharmaceutical compositions and methods of use therefor
EP0915370A1 (en) * 1997-11-04 1999-05-12 Konica Corporation Silver halide light-sensitive photographic material

Also Published As

Publication number Publication date
FR1021379A (fr) 1953-02-18
DE966411C (de) 1957-08-01
NL79254C (xx) 1955-10-15
GB669590A (en) 1952-04-02
CH308746A (de) 1955-07-31
CH288169A (de) 1953-01-15

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