US3918976A - Polyester film with anthroquinone dye for a photographic film support - Google Patents

Polyester film with anthroquinone dye for a photographic film support Download PDF

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Publication number
US3918976A
US3918976A US363702A US36370273A US3918976A US 3918976 A US3918976 A US 3918976A US 363702 A US363702 A US 363702A US 36370273 A US36370273 A US 36370273A US 3918976 A US3918976 A US 3918976A
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Prior art keywords
film
dye
polyester
support
compound
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US363702A
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English (en)
Inventor
Atsuaki Arai
Masaki Okazaki
Noburo Hibino
Kunihira Seto
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Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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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
    • G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
    • G03C1/83—Organic dyestuffs therefor
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
    • C09B1/325—Dyes with no other substituents than the amino groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
    • C09B1/51—N-substituted amino-hydroxy anthraquinone
    • C09B1/514—N-aryl derivatives
    • 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
    • G03C1/795—Photosensitive materials characterised by the base or auxiliary layers the base being of macromolecular substances
    • G03C1/7954—Polyesters

Definitions

  • ABSTRACT A polyethylene terephthalate film for an X ra photographic film support colored blue by one or more anthraquinone dyes represented by the general formula (li NH 0 t CH3 CH3 wherein X represents a hydrogen atom; an alkyl group having ll5 carbon atoms; a cycloalkyl group; an aryl group; an aryl group substituted by an alkyl group having ll0 carbon atoms a carbox ⁇ l group. or a halogen atom; an aralkyl group; or an aralkyl group substituted by an alkyl group having l-IO carbon atoms a carboxyl group or a halogen atom.
  • the present invention relates to a polyester film to be used as a support in a light-sensitive photographic film, and more particularly, to a polyester film for a photographic film support colored blue by an anthraquinone dye.
  • Light-sensitive photographic films having a colored support are known. It is desirable that in light-sensitive photographic materials, particularly in X-ray photographic films, the film support be colored blue to facilitate the discrimination of photographic images.
  • the photographic image formed on an X-ray photographic film prepared by coating an X-ray photographic emulsion on a colorless support film has a soft, poor black tone, and hence it is not easy to clearly see the images formed thereon. This means that when the spectral absorption of the developed silver of the X-ray film is measured, the absorption in the short wave length region is large.
  • the support film is typically colored using a blue dye having absorption in the long wave length region. That is to say, the image of an X-ray photographic film having a support film colored with a blue dye has a sharp or clear black tone, and can be easily distinguished.
  • a support film colored using a dye having absorption in the short wave length region is used as the support for an X-ray photographic film of the type where a photographic emulsion such as a gelatino silver iodobromide emulsion is coated on both surfaces thereof, a filter desensitization action occurs at X-raying.
  • the dyes used for coloring a polyester film for anX-ray photographic film support are required to satisfy various requirements, i.e., to have good heat resistance, sublimation resistance, miscibility with the support film and to have a proper color hue (less yellow component). Further, they must be inactive to the gelatino silver halide emulsion to such an extent that they do not have any harmful influence on the photographic properties thereof, such as sensitivity, gamma, fog, etc.
  • colored polyester films can be prepared by conducting the polycondensation of the components forming the polyester after adding a dye to at least one component prior to the polycondensation, or by mixing a powdery, chip-like or pellet-like polyester with a dye in any proper manner, extruding the mixture into a colored molten sheet by melt extrusion to form a substantially amorphous non-oriented film, biaxially stretching the sheet to about 2.5 times its original dimensions, and heat-treating to provide a film having dimensional stability.
  • Such a method as described above in which the molten material is colored before it is formed into a sheet or film is excellent as compared to other methods in the point that a uniformly colored polyester film is obtained.
  • the coloring dye used is required to have good heat resistance, i.e., it should be capable of enduring temperatures of 270C to 320C.
  • a polyester film has a stable physical structure and hence it is not easy to color the film by dyeing. Therefore, it is preferred, as mentioned above, to employ the method in which the coloring matter is dispersed or dissolved in the polyester by adding it during the synthesis of the polymer or at melting the polymer during heating for molding or fabrication. Therefore, the coloring dye used is required to have a high heat stability so as to endure molding temperatures of 270C to 320C and not decompose and fade.
  • the above-mentioned method of coloring a polyester before it is formed into a sheet or film also has the advantage that it does not need an additional coloring step because the coloring is conducted in the molding step.
  • Polyester is formed into film through the steps of drying, melting by heating, extruding, stretching and heattreating. Among those steps, the drying step is preferably conducted under reduced pressure at temperatures of l35C to 2 [0C (as described in the specification of Japanese patent publication No. 6l8/l953). lfa drying step is not employed in the case of forming a polyester film, hydrolysis occurs upon melting the polyester by heating, which results in making the formation of a film impossible or producing a film having poor properties, e.g., low strength.
  • a polyester film is usually produced using a tenter system, and hence edge loss is inevitable.
  • edge loss is inevitable.
  • the cut-off edges of the polyester film they are collected, pulverized, and dried with fresh polyester chips.
  • the polyester film has been colored with a dye having poor sublimation resistance, the dye used for the coloring sublimates from the cutoff edges during drying. Consequently, not only is dye lost by sublimation, but the dye thus sublimated stains the dryer, and further the sublimed dye is deposited on the inside wall of the dryer and falls down therefrom to cause uneven coloring.
  • polyester when polyester is colored with a prior art coloring matter or dye as described above, the coloring matter or dye sublimates at extruding to stain the casting drum to give an uneven dye density in the colored film. Therefore, it is necessary to color polyesters using coloring matter or a dye which has good sublimation resistance.
  • the polyester When coloring a molten polyester, it is necessary that the coloring dye be easily and uniformly dispersed or dissolved in the polyester and, in particular when the colored polyester is used as a support for a photographic film, the polyester is required to provide a film having high transparency and a surface free of optical defects. Therefore, turbidity cannot be formed in the support film caused by insufficient dispersion of the coloring matter or foreign matter present in the support film.
  • One object of this invention is thus to provide a coloring matter or a dye for coloring a polyester for use as the support of a photographic material satisfying the heretofore described severe conditions regarding photographic properties, heat resistance, sublimation resistance and color hue.
  • a polyester film for use as a support of a photographic film comprising a substantially homogeneous mixture of a polyester and a l,4-diarylaminoanthraquinone dye.
  • X represents a hydrogen atom; an alkyl group having ll 5 carbons atoms, a cycloalkyl group; an aryl group; an aryl group substituted by an alkyl group having 1-10 carbon atoms, a carboxyl group, or a halogen atom; an aralkyl group or an aralkyl group substituted by an alkyl group having 1-10 carbon atoms, a car boxy] group, or a halogen atom.
  • cycloalkyl groups are those having 5 or 6 carbon atoms
  • aryl or ar- 4 alkyl groups most highly preferred are those which are monoaryl and, for aralkyl, where the. alkyl moiety has I or 2 carbon atoms.
  • this narrow class offers superior results.
  • the dye used in this invention is stable even if it is heated for several hours at temperatures above 270C and further is not decomposed even if the dye is heated while dispersed in a molten polyester for more than 3 hours in the absence of air.
  • the dye in this invention has a particularly high sublimation resistance and that the uneven dyeing occurring in the case of using ordinary dyes does not occur under polymerization reaction condition (see US. Pat. No. 2,823,421 to Scarlett) in which the polycondensation is conducted under high vacuum after dispersing the dye in the components forming the polyester or during the step of dispersing the dye in a molten polyester at a high temperature under a high vacuum.
  • the dye of this invention is readily-soluble in ordinary organic solvents such as petroleum saturated hydrocarbons, aromatic hydrocarbons, aliphatic or aromatic halogenated hydrocarbons, ethers, ketones and esters, and hence the dye is suitable for producing an excellent colored support for photographic films by using an ordinary colored subbing layer as described in Japanese Pat. No. 13826/1968 on a transparent synthetic high molecular weight film.
  • ordinary organic solvents such as petroleum saturated hydrocarbons, aromatic hydrocarbons, aliphatic or aromatic halogenated hydrocarbons, ethers, ketones and esters
  • solvents examples include benzene, toluene, chloroform, methylene chloride, ethyl ether, tetrahydrofuran, acetone, methyl ethyl ketone, ethyl acetate and butyl acetate.
  • the polyester used in this invention includes not only those consisting of only repeating units of ethylene terephthalate but also those containing up to about 2% of another component or components in addition to the repeating units of ethylene terephthalate.
  • other components there can be illustrated isophthalic acid, phthalic acid, adipic acid, diethylene glycol, triethylene glycol, propylene glycol, cyclohexane dimethanol, and HO-(CI-I -)-OH, where n is 3 or 8.
  • Compound 12 l,4-bis(2',6'-dimethyl-4'-cyclohexyloxyanilino)-anthraquinone.
  • the dye, or a combination of the dyes of this invention gives an excellent color to a support for photographic films when it (or they) is used in an amount of about 0.01 to about 0.5 g per kilogram of the polyester chips. As one strays further and further outside this preferred range, the excellent results obtainable begin to decrease in effect. Accordingly, it is best to be within the range 0.01 to 0.5 g per kilogram recited.
  • polyester materials as are used in the present invention have an intrinsic viscosity of about 0.55 to about 0.70, determined in a mixture of phenol and tetrachloroethane (1:1 by weight) at C. While it will be obvious to one skilled in the art that this is not a limitative range, polyester materials meeting this criterion are very suitable for use in forming photographic film supports.
  • aminoanthraquinone dyes of the present invention are used in dispersed form in the polyester, best results in forming a photographic film support are obtained when the size thereof is less than the wave length of visible light, most preferably, when the diameter of any vacant spaces formed between the polyester matrix and the particles of the dyes or coloring material is less than one tenth the wave length of visible light (less than about 125 angstroms).
  • Such a product illustrates remarkably low haze, and while this parameter is not limitative, since final product qualities will vary depending on the user, such a product is highly preferred.
  • 1,4-diaminoanthraquinone dyes among the aminoanthraquinone dyes useful for a support for a photographic film, the following dyes are described in, e.g., US. Pat. No. 3,488,195, Japanese patent publication No. 15187/1970, British Pat. No. 1,137,595 and Belgian Pat. No. 700,302;
  • Compound E l,4-bis( 2 ',3 ,4 ,5 ',6'-pentamethylanilino)anthraquinone.
  • the l,4-diarylaminoanthraquinone dyes used in this invention are superior to known l,4-bis(alkyl-substituted anilino)anthraquinone dyes as shown above, and hence the dyes of this invention do not cause uneven coloring in the coloring of molten polyesters.
  • the sublimation resistance of the dyes was tested in the following manner: 2 mg of the dye was placed in the bottom of a hard glass test tube having an inside diameter of 18 mm and a length of 200 mm, and then 10 g of polyethylene terephthalate chips (4 mm X 4 mm X 2.5 mm) was placed on the dye.
  • Several of such test tubes, each containing a different dye, were prepared, connected to vacuum pipe lines and evacuated for 5 minutes under a pressure of 0.1 mm.
  • test tubes were immersed in an oil bath heated to 180C 2C to the whole length of the tubes, and after continuing the evacuation and heating for 4 hours, the test tubes were withdrawn.
  • the compound prepared in this synthesis example was 1,4 bis(2',6'-dimethyl-4'-n-decyloxyanilino)anthraquinone.
  • the product was added to 2000 ml of water containing 60 g of sodium hydroxide and after heating the mixture to 4050C, 200 g of sodium hydrosulfite was added. After heating at C for a further 2 hours, the reaction mixture was cooled and extracted twice with 300 m1 of ethyl ether. The ether layer separated was washed with water, dried over anhydrous sodium sulfate, and ether was evaporated.
  • Visible absorption spectra A 544 nm (sh), 582 nm, and 626 nm.
  • Visible absorption spectra A 544 nm (sh), 582 nm,62.6,,nm.
  • EXAMPLE 1 The dye (Compound 4 prepared in Synthesis example 3-(2) was mixed with polyethylene terephthalate chips (the chips had a size of4 mm X 4 mm X 2.5 mm; chips of this size were used in all examples where chips were used, unless otherwise indicated) and the mixture was kneaded and formed into a film by melt extrusion at 290C so that the film prepared contained 0.025 weight dye. The film was then stretched to give a blue film having a thickness of 0.180 mm. The stretching conditions were: first step, 3.5 times at C; second step, 3.5 times at C. No reduction in transparency and no formation of clouds or turbidity due to nondispersed particles was observed in the film. The casting drum was also not stained by the dye during the formation of the film.
  • Both surfaces of the film were irradiated with ultraviolet rays for 1 minute at 80C in air by means ofa 1 KW quartz mercury lamp as described in Japanese patent publication No. 2603/1968, and then a gelatin dispersion having the following composition was coated on the surfaces and dried for 2 minutes at C to give a gelatin dispersion layer about 6 microns thick.
  • the emulsion layer thickness was 6 microns.
  • the image obtained by X-raying through a human body using the medical X-ray film and developing it could be easily distinguished as a clear image, and the photographic properties such as sensitivity, gamma and fog were not affected.
  • a gelatino silver iodobromide X-ray photographic emulsion containing I g of silver iodide, 60 g of gelatin and 3 mol% of bromine was coated on the surfaces m ofthe colored subbing layers which had been applied to both surfaces of the polyethylene terephthalate film to yield a medical X-ray film.
  • the thickness of the emulsion layer was 7 microns. No harmful influence was observed on the photographic characteristics of the X-ray photograph obtained by X'raying through a human body using the X-ray film. Also, no stains were observed on the developing machine or in the developer used.
  • an X-ray film was prepared in the same way using a comparison dye, l,4-bis(2',4,6'- trimethylanilino)-anthraquinone (Compound B) in place of the dye of the invention in the composition of the subbing layer, and the film developed in an automatic developing machine. In this case the developer was colored blue.
  • EXAMPLE 3 A mixture of 7 parts by weight of the dye (Compound 8) prepared in Synthesis Example 4 and 3 parts of 1,4- bis[ 2 ,4 ',6'-trimethyl-3 -(cyclohexylamido)sulfoanilino]anthraquinone was mixed [The chips and dye were blended in the dry state and melt extruded 290C] with polyethylene terephthalate chips so that the film prepared from the mixture contained 0.025% dyes and then an oriented polyethylene terephthalate film colored blue-violet and having a thickness of0. l 80 mm was prepared as in Example I.
  • the film thus obtained had high transparency and a slightly reddish blue-violet color as compared with the film obtained in Example 1. No stains on the casting drum were observed at the formation of the film.
  • Both surfaces of the film thus prepared were irradiated with ultraviolet rays in the manner described in Example I and coated with a subbing layer coating composition having the same composition as in Example I, followed by drying. Then, a gelatino silver iodobromide emulsion for an X-ray photographic film containing 100 g of silver iodobromide, 60 g of gelatin, and 3 mol% of silver iodide was coated thereon to give a medical X-ray film.
  • the silver image obtained by X- raying a human body using the X-ray film could easily be distinguished as a clear image, and the photographic characteristics such as sensitivity, gamma and fog did not change as compared with those of a control film.
  • EXAMPLE 4 A mixture of 9.5 parts of the dye (Compound 3) prepared in Synthesis Example 2 and 0.5 part of 4,8-dihydroxy l ,5-bis(2,4,6'-trimethylanilino)anthraquinone was mixed with polyethylene terephthalate chips so that the film prepared from the mixture contained 0.020% dyes, and an oriented film colored blue-violet of a thickness of 0.!80 mm was prepared by the same casting method as in Example I.
  • the colored film thus obtained had the same properties as those of the film obtained in Example 4.
  • EXAMPLE 6 A colored polyethylene terephthalate film was prepared using a mixture of 8.8 parts of [l,4-bis(2',6- dimethyl-4'-benzyloxyanilino)anthraquinone] (Compound 4) and L2 parts of l-p-benzyloxyanilino-4- hydroxyanthraquinone according to the procedure of Example 5. The colored film thus obtained had the same properties as those of the film prepared in Example 4.
  • EXAMPLE 7 A colored film was prepared using a mixture of 5.5 parts of l ,4-bis( 2 ',6'-dimethyl-4 '-phenethyloxyanilino)anthraquinone (Compound 8) and 4.5 parts of 1,4-bisl 2 ',6 '-dimethyl-4'-(o-methyl )benzyloxyanilinolanthraquinone (Compound 6) according to the procedure of Example 5.
  • the colored film thus obtained had properties the same as those of the film prepared in Example 4.
  • a photographic film having a support comprising a polyethylene terephthalate film containing at least one compound represented by the formula:
  • X represents a hydrogen atom; an alkyl group having 1-15 carbon atoms; a cycloalkyl group; an aryl group substituted by an alkyl group having l-l carbon atoms, a carboxyl group, or a halogen atom; an aralkyl group; or an aralkyl group substituted by an alkyl group having 1-1 0 carbon atoms, a carboxyl group, or a halogen atom, the size of said compound being less than the wave length of visible light and said compound having been mixed with said polyethylene terephthalate under melting condition and a silver halide light-sensitive emulsion layer coated on said support.
  • a support as claimed in claim 3 wherein the polyethylene terephthalate has an intrinsic viscosity of from about 0.55 to about 0.70, determined in a 1:1 by weight mixture of phenol and tetrachloroethane at 25C.

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  • Engineering & Computer Science (AREA)
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  • General Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
US363702A 1972-05-24 1973-05-24 Polyester film with anthroquinone dye for a photographic film support Expired - Lifetime US3918976A (en)

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Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4116923A (en) * 1976-03-20 1978-09-26 Hoechst Aktiengesellschaft Dyed polyesters, process for their preparation and their use for the dyeing of plastics
US4167490A (en) * 1975-12-22 1979-09-11 E. I. Dupont De Nemours And Company Flexible ultraviolet radiation transmitting filters
US4215030A (en) * 1977-08-31 1980-07-29 Fuji Photo Film Co., Ltd. Photographic polyester film support
US4628025A (en) * 1984-07-13 1986-12-09 Konishiroku Photo Industry Co., Ltd. Polyester support for photographic use
US4788432A (en) * 1987-07-17 1988-11-29 Jp Laboratories, Inc. Radiation monitoring device
US5372864A (en) * 1993-09-03 1994-12-13 Eastman Chemical Company Toners for polyesters
US5382465A (en) * 1987-07-22 1995-01-17 Mitsui Toatsu Chemicals, Incorporated Anthraquinonic colorant and polarizing film containing the colorant
EP0696757A2 (en) 1994-08-09 1996-02-14 Eastman Kodak Company Film for duplicating silver images in radiographic films
US5608031A (en) * 1995-11-30 1997-03-04 Eastman Chemical Company Polyesters modified with 1,4-cyclohexaned imethanol having high clarity prepared utilizing an antimony containing catalyst/stabilizer system
US5620839A (en) * 1993-12-16 1997-04-15 Fuji Photo Film Co., Ltd. Silver halide photographic material
US5750635A (en) * 1995-11-13 1998-05-12 Brink; Andrew Edwin Thermally stable polyesters formed utilizing antimony compounds as catalysts
US5837012A (en) * 1994-10-28 1998-11-17 Fuji Photo Film Co., Ltd. Dyeing method of photographic polyester support
US5962557A (en) * 1996-09-30 1999-10-05 Eastman Chemical Corporation Polyesters containing copolymerized substituted 1,4-bis(2,6-dialkylanilino)-9, 10-anthraquinones as colorants
US6270945B1 (en) * 1997-03-19 2001-08-07 Kodak Polychrome Graphics, Llc Photosensitive compositions and elements comprising dyed photosensitive polyesters
US6413699B1 (en) 1999-10-11 2002-07-02 Macdermid Graphic Arts, Inc. UV-absorbing support layers and flexographic printing elements comprising same
EP1304360A1 (en) * 2001-10-19 2003-04-23 Eastman Chemical Company Reactive anthraquinone colorant compounds and polymeric materials reacted therewith
US20050065247A1 (en) * 2003-09-19 2005-03-24 Carico Douglas Weldon Liquid coating compositions having improved whiteness
US20050253057A1 (en) * 2001-05-05 2005-11-17 Hamilton Thomas J Microprocessor based automatically dimmable eye protection device with interruption prevention
WO2011070122A1 (en) 2009-12-10 2011-06-16 Agfa-Gevaert Security document with security feature on edge
US20140316060A1 (en) * 2011-08-24 2014-10-23 Lambson Limited Polymers Comprising Photoinitiator Moieties and Dye Moieties
US20170137625A1 (en) * 2014-06-17 2017-05-18 Dow Global Technologies Llc Anthraquinone compound used for color filter of lcd

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Publication number Priority date Publication date Assignee Title
JPS5857735B2 (ja) * 1975-01-22 1983-12-21 株式会社日立製作所 放射線検知フイルム

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US2859221A (en) * 1954-12-31 1958-11-04 Geigy Ag J R Acid anthraquinone dyestuffs
US3488195A (en) * 1966-06-29 1970-01-06 Eastman Kodak Co Light-sensitive photographic element
US3849139A (en) * 1971-09-09 1974-11-19 Fuji Photo Film Co Ltd Polyethylene terephthalate film for use as roentgenographic film base

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DE1937486A1 (de) * 1968-07-25 1970-02-19 Fuji Photo Film Co Ltd Roentgenfilm und Verfahren zur Herstellung eines Polyaethylenterephthalatfilms

Patent Citations (3)

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Publication number Priority date Publication date Assignee Title
US2859221A (en) * 1954-12-31 1958-11-04 Geigy Ag J R Acid anthraquinone dyestuffs
US3488195A (en) * 1966-06-29 1970-01-06 Eastman Kodak Co Light-sensitive photographic element
US3849139A (en) * 1971-09-09 1974-11-19 Fuji Photo Film Co Ltd Polyethylene terephthalate film for use as roentgenographic film base

Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4167490A (en) * 1975-12-22 1979-09-11 E. I. Dupont De Nemours And Company Flexible ultraviolet radiation transmitting filters
US4116923A (en) * 1976-03-20 1978-09-26 Hoechst Aktiengesellschaft Dyed polyesters, process for their preparation and their use for the dyeing of plastics
US4215030A (en) * 1977-08-31 1980-07-29 Fuji Photo Film Co., Ltd. Photographic polyester film support
US4628025A (en) * 1984-07-13 1986-12-09 Konishiroku Photo Industry Co., Ltd. Polyester support for photographic use
US4788432A (en) * 1987-07-17 1988-11-29 Jp Laboratories, Inc. Radiation monitoring device
US5382465A (en) * 1987-07-22 1995-01-17 Mitsui Toatsu Chemicals, Incorporated Anthraquinonic colorant and polarizing film containing the colorant
US5372864A (en) * 1993-09-03 1994-12-13 Eastman Chemical Company Toners for polyesters
US5384377A (en) * 1993-09-03 1995-01-24 Eastman Chemical Company Toners for polyesters
US5620839A (en) * 1993-12-16 1997-04-15 Fuji Photo Film Co., Ltd. Silver halide photographic material
EP0696757A2 (en) 1994-08-09 1996-02-14 Eastman Kodak Company Film for duplicating silver images in radiographic films
US5837012A (en) * 1994-10-28 1998-11-17 Fuji Photo Film Co., Ltd. Dyeing method of photographic polyester support
US5780575A (en) * 1995-11-13 1998-07-14 Eastman Chemical Company Thermally stable polyesters formed utilizing antimony compound as catalysts
US5750635A (en) * 1995-11-13 1998-05-12 Brink; Andrew Edwin Thermally stable polyesters formed utilizing antimony compounds as catalysts
US5668243A (en) * 1995-11-30 1997-09-16 Eastman Chemical Company Polyesters modified with 1,4-cyclohexanedimethanol having high clarity prepared utilizing an antimony containing catalyst/stabilizer system
US5650481A (en) * 1995-11-30 1997-07-22 Eastman Chemical Company Polyesters modified with 1,4-cyclohexanedimethanol having high clarity prepared utilizing an antimony containing catalyst/stabilizer system
US5608031A (en) * 1995-11-30 1997-03-04 Eastman Chemical Company Polyesters modified with 1,4-cyclohexaned imethanol having high clarity prepared utilizing an antimony containing catalyst/stabilizer system
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Also Published As

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GB1416460A (en) 1975-12-03
FR2185810B1 (en)) 1977-02-11
JPS4910017A (en)) 1974-01-29
DE2326592A1 (de) 1973-12-06
CA999395A (en) 1976-11-02
FR2185810A1 (en)) 1974-01-04

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