US2685512A - Photographic element containing arylidene derivative of fluorene - Google Patents

Photographic element containing arylidene derivative of fluorene Download PDF

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Publication number
US2685512A
US2685512A US317865A US31786552A US2685512A US 2685512 A US2685512 A US 2685512A US 317865 A US317865 A US 317865A US 31786552 A US31786552 A US 31786552A US 2685512 A US2685512 A US 2685512A
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US
United States
Prior art keywords
photographic element
photographic
layers
ultraviolet
layer
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
US317865A
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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 BE523920D priority Critical patent/BE523920A/xx
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to US317865A priority patent/US2685512A/en
Priority to GB30107/53A priority patent/GB735417A/en
Priority to FR1094899D priority patent/FR1094899A/fr
Application granted granted Critical
Publication of US2685512A publication Critical patent/US2685512A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • 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

  • This invention relates to new photographic elements protected against the harmful effects of ultraviolet radiation.
  • R. represents an aryl group, such as phenyl, o, m, and p-tolyl, 0-, m, and p-chlorophenyl, o, m, and p-bromophenyl, o-, m, and p-methoxyphenyl, o-, m, and p-sulfophenyl, o-, m, and p-carboxyphenyl, etc.
  • aryl group such as phenyl, o, m, and p-tolyl, 0-, m, and p-chlorophenyl, o, m, and p-bromophenyl, o-, m, and p-methoxyphenyl, o-, m, and p-sulfophenyl, o-, m, and p-carboxyphenyl, etc.
  • FIG. 1 illustrates schematically a cross-sectional view of a sensitive photographic element having an ultraviolet filter layer containing one of the compounds repre-
  • These 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 pro" tection 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 resulting mixture coated over the lightsensitive layer of the photographic element.
  • a colloidal binder such as gelatin, cellulose esters (e. g. cellulose acetate, etc.), synthetic resins (e. g. polyvinyl acetals, hydrolyzed polyvinyl acetate, etc.), etc.
  • 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 sensitiv 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 which the material is to be put.
  • the support of the photographic element can be transparent, such as a cellulose ester support, for the support can be opaque, such as a paper support.
  • Other supports, such as glass, metal, etc., can be employed, if desired.
  • Example 1 2.0 g. (0.087 g. atom) of sodium were dissolved in 190 cc. of absolute ethanol. To this solution were added 10.0 g. (0.060 mole.) of fluorene (92% purity) and 6.0 g. (-0.57 mole) .of vbenzaldehyde.
  • Example 1 The following example briefly describes the manner of using the compound obtained in Example 1 in a photographic element.
  • Example 2 The compound obtained in Example 1 above dissolved in tricresyl phosphate in a 1:3 ra io, and this solution was mixed with a gelatin dispersion which was coated :on film. A separate ccating on paper was also made, After one weeks exposure on an east window, the coatings showed neither fading nor print-out. A square of the film coating was placed over a paper coatcontaining a standard magenta coupler, and this was exposed in a similar manner to ulta violet radiation. No fading nor print-out was observed in the magenta layer.
  • ether compounds selected from those represented by the above general formula can be employed.
  • the following are typical compounds which can be employed in my invention.
  • FIG. 1 illustrates schematically a cross-sectional view of a photographic element containing a layer having incorporated therein S-benzal'fiuorene, which is representative of the ultraviolet absorbing agents which can be employed in my invention.
  • a support H] of any suitable material such as cellulose acetate or paper, having thereon a sensitive emulsion layer H-is coated with a filter layer 12 having incorporated therein ll-benzalfiuorene, or some other ultraviolet absorbing compound selected from those represented by the above general formula.
  • the drawing is merely representativ of other structures which can be employed in my invention, and that the element can have other layers, not shown, such as additional light-sensitive layers, subbing layers, antihalation layers, etc.
  • the ultraviolet absorbing compound contains a solubiiizing group, such as carboxyl ,.hydroxy1, 'sulfo, etc.
  • the compound can be incorporated into the photographic element by bathing the photographic element in an aqueous solution of the ultraviolet absorbing compound.
  • the ultraviolet absorbing compound is concentrated mostly in the outside gelatin overcoat, although it is also present in the remaining layers containing gelatin.
  • the ultraviolet absorbing compound can be incorporated in the photographic element during the preparation thereof, or the ultraviolet absorbing compound can be incorporated in the finished and processed element in those cases where the element has an opaque support, such as paper, in which case, the ultraviolet absorbing compound functions primarily as a stabilizer for the images subject to fading upon exposure to ultraviolet radiation. Such would be the case where the photorap'hic element isa multilayer material.
  • a photographic element having thereon a photographic silver halide emulsion layer and in one of the layers of said element a compound selected from those represented by the following general formula:
  • a photographic element comprising a support, at least one photographic gelatino-silver halide emulsion layer, and coated over said photographic gelatino-silver halide emulsion layer a gelatin layer containing a compound selected from those represented by the following general formula:
  • R is an aryl group
  • R represents an aryl group

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (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)
  • Compositions Of Macromolecular Compounds (AREA)
US317865A 1952-10-31 1952-10-31 Photographic element containing arylidene derivative of fluorene Expired - Lifetime US2685512A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
BE523920D BE523920A (en, 2012) 1952-10-31
US317865A US2685512A (en) 1952-10-31 1952-10-31 Photographic element containing arylidene derivative of fluorene
GB30107/53A GB735417A (en) 1952-10-31 1953-10-30 Photographic materials containing ultraviolet radiation absorbing compounds
FR1094899D FR1094899A (fr) 1952-10-31 1953-10-30 Procédé de protection contre l'ultraviolet et ses applications, notamment en photographie

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US317865A US2685512A (en) 1952-10-31 1952-10-31 Photographic element containing arylidene derivative of fluorene

Publications (1)

Publication Number Publication Date
US2685512A true US2685512A (en) 1954-08-03

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Family Applications (1)

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US317865A Expired - Lifetime US2685512A (en) 1952-10-31 1952-10-31 Photographic element containing arylidene derivative of fluorene

Country Status (4)

Country Link
US (1) US2685512A (en, 2012)
BE (1) BE523920A (en, 2012)
FR (1) FR1094899A (en, 2012)
GB (1) GB735417A (en, 2012)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2784087A (en) * 1954-09-20 1957-03-05 Eastman Kodak Co Photographic light sensitive elements containing ultra-violet filters
US2984568A (en) * 1956-11-26 1961-05-16 Gevaert Photo Prod Nv Photographic antihalation and protective layer comprising a nitrated styrene-maleic acid copolymer
WO2013103139A1 (ja) 2012-01-06 2013-07-11 コニカミノルタアドバンストレイヤー株式会社 フィルムミラー、フィルムミラーの製造方法、太陽熱発電用フィルムミラー及び太陽熱発電用反射装置

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2784087A (en) * 1954-09-20 1957-03-05 Eastman Kodak Co Photographic light sensitive elements containing ultra-violet filters
US2984568A (en) * 1956-11-26 1961-05-16 Gevaert Photo Prod Nv Photographic antihalation and protective layer comprising a nitrated styrene-maleic acid copolymer
WO2013103139A1 (ja) 2012-01-06 2013-07-11 コニカミノルタアドバンストレイヤー株式会社 フィルムミラー、フィルムミラーの製造方法、太陽熱発電用フィルムミラー及び太陽熱発電用反射装置

Also Published As

Publication number Publication date
GB735417A (en) 1955-08-17
BE523920A (en, 2012)
FR1094899A (fr) 1955-05-25

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