US3365295A - Ultra-violet absorbing filters - Google Patents

Ultra-violet absorbing filters Download PDF

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Publication number
US3365295A
US3365295A US389538A US3365295DA US3365295A US 3365295 A US3365295 A US 3365295A US 389538 A US389538 A US 389538A US 3365295D A US3365295D A US 3365295DA US 3365295 A US3365295 A US 3365295A
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US
United States
Prior art keywords
ultra
alkyl
violet
carbon atoms
violet absorbing
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
US389538A
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English (en)
Inventor
Fritz Nittel
Hans Ulrich
Heinz Meckl
Hans-Georg Kleppe
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Agfa Gevaert NV
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Agfa AG
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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
    • C07D277/32—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 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/54—Nitrogen and either oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/45—Heterocyclic compounds having sulfur in the ring
    • C08K5/46—Heterocyclic compounds having sulfur in the ring with oxygen or nitrogen in the ring
    • C08K5/47—Thiazoles
    • 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

  • the ultraviolet absorbing compounds have to meet certain conditions.
  • -above compounds may be prepared according to the following general method 0.1 mol of the thiosemicarbazone (A), 0.12 mol of the a-bromoalkylcarboxylic acid ethyl ester (B) and 24 g. of pyridine are dissolved in a suliicient amount of ethanol (about 100-500 ml.) and refluxed for 6 hours.
  • the other compounds can be prepared in analogous manner.
  • the ultra-violet absorbing compounds to be used according to the invention represent crystalline or waxy substances of good solubility and emulsifiability.
  • the compounds are distinguished by high mo-lar extinction, good light stability and a decay of absorption at the -boundary of the visible spectral region (see the accompanying drawings).
  • high-boiling organic solvents such as phosphoric acid esters or esters ⁇ of polybasic carboxylic acids such as phthalic or adipic acid.
  • the use of the compounds is not restricted to color photographic purposes; it can also be extended to any desired other elds of use, such as plastic foils, light iilters and packing materials.
  • Example 1 760 ml. of aqueous gelatin solution and 40 ml. of a 10% aqueous solution of dodecyl benzene sulfonate as emulsier are vigorously stirred in an emulsifying apparatus and a solution consisting of 20 g. of the compound XIII dissolved in 50 rnl. of ethyl acetate, is slowely added. The mixture is stirred for -20 minutes. After cooling, the solidied mass is formed into noodles and dried. The dried emulsion is completely clear. It is applied as a 2-5% aqueous solution as a protective layer onto a light-sensitive multilayer color photographic material. Layer thickness: 1-5 microns.
  • a solution suitable for casting can also be prepared by diluting the 10% emulsion to a 2-5% solution instead of drying it.
  • a 2-5% gelatin solution may be used.
  • the example can be modified in such a way that up to 50% of the weight of gelatin is replaced by the ultraviolet absorbing compound.
  • the improvement in the fastness is determined by an image with an ultra-violet protective layer and an image with a pure gelatin protective layer being exposed until the same degree of fading is reached.
  • the ratio of the lux hours required gives the improvement factor.
  • Example 2 To illustrate the stability of the compounds of the present invention to ultra-violet light and to show the absorption characteristics of the compounds, the following tests were made:
  • Example 3 ml. of 10% aqueous gelatin solution and 10 ml. of a 10% aqueous s-olution of saponine as emulsiiier are mixed in the manner referred to in Example 1 with 2 g. of the compound V dissolved in 25 ml. of ethyl acetate, and further processed as in Example l.
  • the ultra-violet absorber layers obtained in accordance with the above examples are completely clear, withstand the col-or processing without any change and do not show any exudation phenomena under high glaze drying. No precipitation occurs during the storage of the aqueous heated emulsions.
  • Example 1 100 ml. of 10% aqueous gelatin solution and 10 ml. of a 10% aqueous solution of saponine as emulsiiier are mixed in the manner referred to in Example 1 with 2 g. of the compound XIX dissolved in 15 ml. of ethyl acetate, and further processed as in Example l.
  • the ultra-violet absorber layers obtained are completely clear, withstand the color processing without any change and do not show any exudation phenomena under high glaze drying. No precipitation occurs during the storage of the aqueous heated emulsions.
  • Example 5 A color photographic image in a processed multilayer film or paper strip is coated with an ultra-violet absorbing layer as Idescribed in Example 1. Measuring of the coated element indicates a considerable density to ultra-violet light. The light fastness of the color photograph is improved by the factor 10 as compared with a color photograph of the same type without a protective layer. The thickness of the layer is about 3 microns.
  • the thickness of the ultra-violet absorbing layer is preferably between l and 10 microns, more preferably between 1 and 5 microns.
  • the layer may contain between 5 and 50% by weight of the ultra-Violet absorbing compounds based on the weight of the dried layer.
  • R and R each represent a member of the group consisting of hydrogen, alkyl having up to 18 carbon atoms, and aryl;
  • R stands for a member of the group consisting of hydrogen and alkyl having up to i8 carbon atoms
  • X and Y each represent a member of the group consisting of hydrogen, halogen, hydroxyl, alkoxy the alkyl of which has up to 18 carbon atoms, carboxyl, esteried carboxyl. carbonamide, nitril, sulfo, amino, alkyl substituted amino, aryl substituted amino, acyl substituted amino, alkyl having up to 1S carbon atoms, hydroxy substituted alkyl and alkoxy substituted alkyl.
  • I?. and R each represent a member of the group consisting of hydrogen, alkyl having up to 18 carbon atoms, and aryl;
  • R stands for a member of the group consisting of hydrogen and alkyl having up to 1S carbon atoms.. and
  • X and Y each represent a member of the group consisting of hydrogen, halogen, hydroxyl, alkoxy the alkyl of which has up to 18 carbon atoms, carboxyl, estenl ied carboxyl, carbonamide, nitril, sulfo, amino,
  • alkyl substituted amino alkyl substituted amino, aryl substituted amino, acyl substituted amino, alkyl having up to 18 carbon atoms, hydroxy substituted alkyl and alkoxy substituted alkyl.
  • a finished color photographic element comprising a support having thereon a plurality of processed photographic emulsion layers Containing coupled-dye images at least one of said dye images being subject to fading by the action of ultra-violet radiation, the layer containing said image being arranged between said support and a protective layer containing an effective amount of an ultraviolet absorbing compound of the following formula wherein R and R" each represent a member of the group consisting of hydrogen, alkyl having up to 18 carbon atoms, and aryl;
  • R stands for a member of the group consisting of hydrogen and alkyl having up to 1S carbon atoms
  • X and Y each represent a member of the group Consisting of hydrogen, halogen, hydroxyl, alkoxy the alkyl of which has up to 18 carbon atoms, carboxyl, csteried carboxyl, carbonamide, nitril, sulfo, amino, alkyl substituted amino, aryl substituted amino, acyl substituted amino, alkyl having up to 18 carbon atoms, hydroxy substituted alkyl and alkoxy substituted alkyl.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Paper (AREA)
US389538A 1963-09-07 Ultra-violet absorbing filters Expired - Lifetime US3365295A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEA43995A DE1187928B (de) 1963-09-07 1963-09-07 Ultraviolettes Licht absorbierendes Filter

Publications (1)

Publication Number Publication Date
US3365295A true US3365295A (en) 1968-01-23

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US389538A Expired - Lifetime US3365295A (en) 1963-09-07 Ultra-violet absorbing filters

Country Status (5)

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US (1) US3365295A (de)
BE (1) BE652739A (de)
CH (1) CH453892A (de)
DE (1) DE1187928B (de)
GB (1) GB1054120A (de)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3503779A (en) * 1965-07-08 1970-03-31 Monsanto Co Substrates coated with polymeric ultraviolet light barrier coatings
US3506470A (en) * 1965-07-08 1970-04-14 Monsanto Co Photoprints coated with polymeric ultraviolet light barrier coatings
US3604081A (en) * 1969-06-04 1971-09-14 Zenith Radio Corp Screening a color cathode-ray tube

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2798067A (en) * 1954-03-29 1957-07-02 Eastman Kodak Co 2-imino-4-thiazolidones and preparation

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2798067A (en) * 1954-03-29 1957-07-02 Eastman Kodak Co 2-imino-4-thiazolidones and preparation

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3503779A (en) * 1965-07-08 1970-03-31 Monsanto Co Substrates coated with polymeric ultraviolet light barrier coatings
US3506470A (en) * 1965-07-08 1970-04-14 Monsanto Co Photoprints coated with polymeric ultraviolet light barrier coatings
US3604081A (en) * 1969-06-04 1971-09-14 Zenith Radio Corp Screening a color cathode-ray tube

Also Published As

Publication number Publication date
GB1054120A (de)
DE1187928B (de) 1965-02-25
BE652739A (de) 1965-03-08
CH453892A (de) 1968-03-31

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