US2808330A - Photographic elements containing thiazolidine derivatives - Google Patents

Photographic elements containing thiazolidine derivatives Download PDF

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Publication number
US2808330A
US2808330A US317864A US31786452A US2808330A US 2808330 A US2808330 A US 2808330A US 317864 A US317864 A US 317864A US 31786452 A US31786452 A US 31786452A US 2808330 A US2808330 A US 2808330A
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US
United States
Prior art keywords
photographic
ultraviolet
phenyl
thiazolidone
phenylimino
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
Application number
US317864A
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English (en)
Inventor
George W Sawdey
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eastman Kodak Co
Original Assignee
Eastman Kodak Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to BE523919D priority Critical patent/BE523919A/xx
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to US317864A priority patent/US2808330A/en
Priority to DEE7988A priority patent/DE969374C/de
Priority to GB30106/53A priority patent/GB748190A/en
Priority to FR1089671D priority patent/FR1089671A/fr
Priority to GB8963/55A priority patent/GB770494A/en
Priority to DEE10457A priority patent/DE1002625B/de
Priority to FR69670D priority patent/FR69670E/fr
Application granted granted Critical
Publication of US2808330A publication Critical patent/US2808330A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • 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
    • 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
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/132—Anti-ultraviolet fading

Definitions

  • This invention relates to new products and new photographic elements proteeted against the harmful effects of ultraviolet radiation.
  • an object of my invention to provide new compounds and against the harmful effects of ultraviolet radiation.
  • a further object is to provide photographic color materials which have been protectedagainst the harmful effects of ultraviolet radiation.
  • Other objects will becomeappatent from a consideratio'nof the'following description.
  • R represents a hydrogen atom, an alkyl group photographic elements protected trite States Patent (e. g. methyl, ethyl, propyl, isopropyl, etc.),
  • R1 represents an aryl group (e. g. phenyl, o-, m-, propylphenyl, o-, m-, and p-hydroxyphenyl, o-, m-, and p-sulfophenyl (and alkali metal salts thereof, e. g. sodium, potassium, etc.), 4-methoxy-3-sulfophenyl (and alkali metal salts, thereof,. e.
  • the accompanying drawing illustrates schematically a cross-sectional view of a sensitive photographic element having an ultraviolet filter layer containing one of the compounds represented by the above general formula.
  • ultraviolet absorbing compounds can. be incorporated in the photographic element in a variety of ways, depending on the ultimate use of the photographic element and the degree of protection desired.
  • the ultraviolet absorbing compound can be dissolved or dispersed in a solvent medium together with a colloidal binder, such as gelatin, cellulose esters (e. g. cellulose acetate, etc.), synthetic resins (e. g. polyvinyl acetals, hydrolyzed polyvinyl acetate, etc.), etc., and
  • the ultraviolet filter layer need not be an outer layer, but this layer. can. be placed over one of the layers subject to the harmful effects of ultraviolet radiation.
  • the ultraviolet filter layer can be placed between the blue and green sensitive layers.
  • the ultraviolet filter layer can be placed between the green and the red sensitive layers.
  • the material useful in absorbing the ultraviolet radiation can be incorporated directly in the light-sensitive emulsion instead of, or in addition to, being present in another layer.
  • the amount of ultraviolet absorbing compound used can be varied, depending upon the effect desired and the use to whichthe material is to-be put.
  • the Water-soluble compounds of Formula I above can be incorporated into the photographic element by simply bathing the element in an aqueous solution containing the ultraviolet absorbing compound. Where the outer layer contains gelatin, the ultraviolet absorbing compound becomes adsorbed to this layer.
  • a resinous mordant e. g. polyvinyl pyridine methyl p-toluenesulfonate, phenol-formaldehyde ion exchange resins, etc, in the outer gelatin layer (or an intermediate layer where desired), the photographic,
  • the element can be subjected to Washing or processing operations without removal of the ultraviolet absorbing compounds.
  • the ultraviolet absorbing compounds can be incorporated into the photographic element before or after (i. e. during processing) exposure.
  • the support of the photographic element can be transparent, such as a etc.) support, or a paper support. glass, metal, etc. can be employed,
  • Rr-Pl-H wherein R1 has the values given above.
  • An inert diluent e. g. acetic acid, methanol, ethanol, etc. can be used, if desired.
  • Condensing agents such as piperidine, acetic anhydride, etc. can be employed, if desired.
  • the compounds of Formula I wherein R1 contains a sulfo or carboxyl group are new compounds and are especially useful in the bathing treatment mentioned above. They are useful in the process described in Edgerton and Stand application Serial No. 318,096, filed on even date herewith now U. S. Patent 2,747,996, issued May 29, 1956, being useful either in a layer of the photographic element, or in the bathing solutions disclosed therein. 'The compounds of Formula I can also be added to the photographic silver halide emulsion, though usually less advantageously than when employed in a separate filter layer.
  • the solid formed was filtered out of the hot solution, washed with 2-25 ml. portions of cold methyl alcohol and crystallized from 200 ml. of acetonitrile.
  • the colorless needle-like product had a melting point of 157- alcoholic alkali. (sodium hydroxide) solution,- and the mixture shaken for several minutes.
  • the 5:[3:(3-chlorosulfonylbenzamido)benzal]-3-phenf yI-Z-phenylimino-4-thiazolidone thus obtained was suspended in an alcoholic alkali (sodium hydroxide) solution, whereupon the desired, above-formulated sodium salt was obtained.
  • the resulting solution was used directly for bathing of film or paper strips having thereon a developed and fixed photographic image.
  • this bath could be applied to protect or to fortify the action of an absorber already incorporated in the material.
  • photographic elements containing a photographic silver halide emulsion layer can be treated with other ultraviolet absorbing compounds embraced by Formula I above.
  • the ultraviolet absorbing compound is not water-soluble, it can be incorporated in the gelatin solution with the aid of an inert solvent, e. g. ethanol, and be uniformly dispersed throughout the gelatin solution before coating.
  • the accompanying drawing illustrates schematically a cross-sectional view of a photographic element containing a layer having incorporated therein the' sodium salt of 3 phenyl 2 phenylimino 5 (2'- sulfobenzal) 4- thiazolidone, which is representative-of the ultraviolet absorbing agents which can be employed in my invention.
  • a support 10 of any suitable material, such as celluloseacetate, or paper, having thereon an emulsion layer 11 is coated with a filterlayer 12 having incorporated therein the sodium salt of 3-phenyl-2-phenylimino-5-(2 sulfobenza1) 4-thiazolidone, or some other ultraviolet absorbing'cornpound selected from those represented by the above general formula (I).
  • the drawing is merely representative of other structures which can be employed in my invention, and that the element can have.
  • a finished photographic element comprising a support having thereon a plurality of developed and fixed photographic emulsion layers containing coupled-dye images, at least one of said dye images being subject to fading by the action of ultraviolet radiation, said emulsion layer containing a coupled-dye image subject to fading lying between said s'upportand a gelatin layer containing an'ultraviolet absorbing compoundselected from the group consisting of 5-benzal-3-ethylrhodanine and 5-benzal-3-methyl-2,4-thiazolidinedione.
  • a photographic element according to claim 1 wherein the support is a paper support.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
US317864A 1952-10-31 1952-10-31 Photographic elements containing thiazolidine derivatives Expired - Lifetime US2808330A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
BE523919D BE523919A (US07122603-20061017-C00045.png) 1952-10-31
US317864A US2808330A (en) 1952-10-31 1952-10-31 Photographic elements containing thiazolidine derivatives
DEE7988A DE969374C (de) 1952-10-31 1953-10-21 Gegen Einwirkung der ultravioletten Strahlung geschuetztes photographisches Material mit einer Ultraviolett absorbierenden Schicht
FR1089671D FR1089671A (fr) 1952-10-31 1953-10-30 Procédé de protection contre l'ultraviolet, ses applications, notamment en photographie, et nouveaux composés pour sa misc en oeuvre
GB30106/53A GB748190A (en) 1952-10-31 1953-10-30 Photographic elements containing ultraviolet radiation absorbing compounds
GB8963/55A GB770494A (en) 1952-10-31 1955-03-28 Ultraviolet radiation absorbing compounds and photographic elements containing such compounds
DEE10457A DE1002625B (de) 1952-10-31 1955-03-28 Gegen Einwirkung der Ultraviolettstrahlung geschuetztes photographisches Material
FR69670D FR69670E (fr) 1952-10-31 1955-03-29 Procédé de protection contre l'ultraviolet, ses applications, notamment en photographie et nouveaux composés pour sa mise en oeuvre

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US317864A US2808330A (en) 1952-10-31 1952-10-31 Photographic elements containing thiazolidine derivatives
US770494XA 1954-03-29 1954-03-29

Publications (1)

Publication Number Publication Date
US2808330A true US2808330A (en) 1957-10-01

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ID=26758828

Family Applications (1)

Application Number Title Priority Date Filing Date
US317864A Expired - Lifetime US2808330A (en) 1952-10-31 1952-10-31 Photographic elements containing thiazolidine derivatives

Country Status (5)

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US (1) US2808330A (US07122603-20061017-C00045.png)
BE (1) BE523919A (US07122603-20061017-C00045.png)
DE (2) DE969374C (US07122603-20061017-C00045.png)
FR (2) FR1089671A (US07122603-20061017-C00045.png)
GB (2) GB748190A (US07122603-20061017-C00045.png)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3060029A (en) * 1960-09-12 1962-10-23 Gen Aniline & Film Corp Photographic ultraviolet absorbers
US3097100A (en) * 1960-01-25 1963-07-09 Eastman Kodak Co Thiazolidones as light stabilizers for plastic compositions
US3214463A (en) * 1960-05-12 1965-10-26 Du Pont Uv-absorbing sulfonated benzophenone derivatives
US3352673A (en) * 1963-10-28 1967-11-14 Eastman Kodak Co Multilayer color photographic element
US3460942A (en) * 1959-01-14 1969-08-12 Polaroid Corp Color diffusion transfer process utilizing ultraviolet light absorbers
EP1776112A2 (en) * 2004-08-10 2007-04-25 Exelixis, Inc. Heterocyclic compounds as pharmaceutical agents

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE623419A (US07122603-20061017-C00045.png) * 1961-10-10
US3314794A (en) * 1964-05-13 1967-04-18 Eastman Kodak Co Ultraviolet absorbers
JPS57144633A (en) * 1981-03-05 1982-09-07 Inoue Japax Res Inc Wire electrode feeder

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR788511A (fr) * 1934-04-07 1935-10-11 Gevaert Photo Producten Procédé pour réaliser le développement d'émulsions photographiques en évitant la formation d'un voile
AT145203B (de) * 1934-04-07 1936-04-10 Gevaert Photo Prod Nv Verfahren zur schleierfreien Entwicklung photographischer Emulsionen.
US2160907A (en) * 1936-03-31 1939-06-06 Eastman Kodak Co Filter for ultra-violet light
US2241239A (en) * 1939-01-23 1941-05-06 Eastman Kodak Co Ultraviolet light filter
US2429469A (en) * 1945-06-01 1947-10-21 Eastman Kodak Co Thioketones containing a cycloalkyl group
US2481953A (en) * 1944-10-25 1949-09-13 Gevaert Company Cyanine dyestuffs and process of making same

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE654900C (de) * 1933-11-04 1938-01-04 I G Farbenindustrie Akt Ges Ultraviolett absorbierendes Lichtfilter
NL44804C (US07122603-20061017-C00045.png) * 1935-04-05
AT151660B (de) * 1935-06-01 1937-11-25 Gevaert Photo Prod Nv Verfahren zur Blauschwarzentwicklung und der Schleierverminderung bei photographischen Entwicklungsemulsionen.
GB524378A (en) * 1939-01-23 1940-08-05 Kodak Ltd Method and materials for absorbing short-wave light
GB524377A (en) * 1939-01-23 1940-08-05 Kodak Ltd Method and materials for absorbing short-wave light
GB524379A (en) * 1939-01-23 1940-08-05 Kodak Ltd Method and materials for absorbing short-wave light
DE873733C (de) * 1942-07-24 1953-04-16 Hydrierwerke A G Deutsche Lichtschutzmittel
GB598593A (en) * 1945-02-09 1948-02-23 Kodak Ltd Improvements in sensitive photographic materials
DE820257C (de) * 1947-05-23 1951-11-08 Gen Aniline & Film Corp Transparentes, filmbildendes plastisches Material
US2614940A (en) * 1948-12-31 1952-10-21 Gen Aniline & Film Corp Ultraviolet light absorbing film

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR788511A (fr) * 1934-04-07 1935-10-11 Gevaert Photo Producten Procédé pour réaliser le développement d'émulsions photographiques en évitant la formation d'un voile
AT145203B (de) * 1934-04-07 1936-04-10 Gevaert Photo Prod Nv Verfahren zur schleierfreien Entwicklung photographischer Emulsionen.
GB454870A (en) * 1934-04-07 1936-10-08 Gevaert Photo Producten Naamlo Improvements in or relating to photographic developing
US2099374A (en) * 1934-04-07 1937-11-16 Gevaert Photo Production N V Photographic developer and a process of photographic developing
US2160907A (en) * 1936-03-31 1939-06-06 Eastman Kodak Co Filter for ultra-violet light
US2241239A (en) * 1939-01-23 1941-05-06 Eastman Kodak Co Ultraviolet light filter
US2481953A (en) * 1944-10-25 1949-09-13 Gevaert Company Cyanine dyestuffs and process of making same
US2429469A (en) * 1945-06-01 1947-10-21 Eastman Kodak Co Thioketones containing a cycloalkyl group

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3460942A (en) * 1959-01-14 1969-08-12 Polaroid Corp Color diffusion transfer process utilizing ultraviolet light absorbers
US3097100A (en) * 1960-01-25 1963-07-09 Eastman Kodak Co Thiazolidones as light stabilizers for plastic compositions
US3214463A (en) * 1960-05-12 1965-10-26 Du Pont Uv-absorbing sulfonated benzophenone derivatives
US3060029A (en) * 1960-09-12 1962-10-23 Gen Aniline & Film Corp Photographic ultraviolet absorbers
US3352673A (en) * 1963-10-28 1967-11-14 Eastman Kodak Co Multilayer color photographic element
EP1776112A2 (en) * 2004-08-10 2007-04-25 Exelixis, Inc. Heterocyclic compounds as pharmaceutical agents
US20080132519A1 (en) * 2004-08-10 2008-06-05 Exelixis, Inc. Heterocyclic Compounds As Pharmaceutical Agents
EP1776112A4 (en) * 2004-08-10 2009-11-25 Exelixis Inc HETEROCYCLIC COMPOUNDS AS PHARMACEUTICAL AGENTS
US7902237B2 (en) 2004-08-10 2011-03-08 Exelixis, Inc. Heterocyclic compounds as pharmaceutical agents

Also Published As

Publication number Publication date
BE523919A (US07122603-20061017-C00045.png)
FR1089671A (fr) 1955-03-21
DE969374C (de) 1958-05-22
GB770494A (en) 1957-03-20
DE1002625B (de) 1957-02-14
FR69670E (fr) 1958-11-18
GB748190A (en) 1956-04-25

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