US2719086A - Photographic element - Google Patents

Photographic element Download PDF

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Publication number
US2719086A
US2719086A US317904A US31790452A US2719086A US 2719086 A US2719086 A US 2719086A US 317904 A US317904 A US 317904A US 31790452 A US31790452 A US 31790452A US 2719086 A US2719086 A US 2719086A
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United States
Prior art keywords
group
photographic
layer
photographic element
ultraviolet
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Expired - Lifetime
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US317904A
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English (en)
Inventor
George W Sawdey
Loria Anthony
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Eastman Kodak Co
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Eastman Kodak Co
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Publication date
Priority to BE523922D priority Critical patent/BE523922A/xx
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to US317904A priority patent/US2719086A/en
Priority to DEE7989A priority patent/DE964654C/de
Priority to GB30108/53A priority patent/GB745704A/en
Priority to FR1102962D priority patent/FR1102962A/fr
Priority to US408576A priority patent/US2756253A/en
Application granted granted Critical
Publication of US2719086A publication Critical patent/US2719086A/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

  • ⁇ It is known that certain materials such as cellulosic films and photographic layers are adversely affected by ultraviolet radiation when such materials are exposed to daylight.
  • the ultraviolet radiation sometimes causes undesiredexposure of the layer, or layers, since photographic silver halide emulsions are sensitive to blue, Violet and ultraviolet regions of the spectrum, in addition to any other sensitivity which may be given them, and in the exposure of such material, it is frequently desirable to prevent the action of ultraviolet light on the sensitive emulsion. This is especially true in the case of photographic materials designed for use in color photography where the film has been sensitized to the longer wavelength regions where it is desirable to record only the rays of the visible spectrum.
  • R represents an alkyl (e. g. methyl, ethyl, propyl,
  • R1 represents an organic group selectedV from the group consisting of an aryl group and an aryloxymethyl group, said organic group being substituted by a radical selected from the group consisting of sulfo (including alkali metal salts thereof, e. g. sodium, potassium, etc.), and carboxyl (including alkali metal salts thereof, e. g. sodium, potassium, etc.), e. g. o, m, and p-sulfophenyl, o, m, and p-carboxyphenyl, 3,5-dicarboxyphenoxymethyl, etc.
  • sulfo including alkali metal salts thereof, e. g. sodium, potassium, etc.
  • carboxyl including alkali metal salts thereof, e. g. sodium, potassium, etc.
  • 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.
  • These ultraviolet absorbingy 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 resulting mixture coated over the light-sensitive 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 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. 'I'he 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, or the support can be opaque, such as a ⁇ paper support.
  • Other supports, such as glass, metal, etc., can lbe employed, if desired.
  • Typical compounds selected from those represented by Formula I which can be used in practicing our invention comprise those represented by the following formulas:
  • R and R1 have the values given above and X represents a halogen atom, e. g. chlorine, bromine, etc.
  • X represents a halogen atom, e. g. chlorine, bromine, etc.
  • the condensations can advantageously be effected in the presence of a diluent, e. g. acetonitrile, 1,4-dioxane, etc. Heating is not generally necessary, since the reaction is exothermic.
  • the intermediates II can be prepared by reduction of the corresponding nitro derivatives:
  • the sulfo compounds can advantageously be obtained in the form of the sulfonic acid chloride, which undergoes hydrolysis in the presence of the water present in the bathing or coating solutions.
  • the 3,5-dicarboxyphenoxymethyl (R1) compounds are iirst obtained in the form of their alkyl esters (e. g. methyl, ethyl, etc.), which can be easily hydrolyzed in aqueous alkali (e. g. sodium hydroxide, sodium carbonate, etc.) to the salts of the respective carboxylic acids.
  • the dimethyl ester thus obtained was suspended in alcoholic alkali and shaken at room temperature for several minutes. Spontaneous hydrolysis of the dimethyl ester occurred, yielding the sodium salt of the desired acid.
  • This sodium salt can be used directly, or the reaction medium brought to a neutral pH.
  • the a (3,5 dicarbomethoxyphenoxy)acetal chloride used in the above example was prepared by condensing 5-hydroxyisophthalic acid dimethyl ester with the sodium salt of chloroacetic acid in the presence of sodium methoxide.
  • the sodium salt of the resulting substituted phenoxy acetic acid was treated with phosphorous pentachloride (in ligroin) to yield the desired acid chloride.
  • the 5hy droxyisophthalic acid dimethyl ester was obtained by treating 5-hydroxyisophthalic acid with sulfonylchloride to produce the dicarboxylic acid chloride, followed by treatment with methanol.
  • This compound was prepared in the same manner as that of Example 1 above, except that -n-dodecylresorcinol was employed in place of the -n-hexylresorcinol of Example 1.
  • the dimethyl ester of the desired compound had a melting point of 146-148" C.,-and the following results were obtained upon analysis:
  • the chlorosulfonyl compound thus produced was suspended in an alcoholic alkali solution, thus yielding the desired sodium salt.
  • Example 4 Applicati0n to photographic element l g. of the chlorosulfonyl compound obtained in Example 3, having a melting point of 15G-151 C., was dissolved in a mixture of 6 ml. of ethyl alcohol and 5 ml. of aqueous vsodium hydroxide, containing 10% by weight of the sodium hydroxide. This solution was added to 89 ml. of water and the pH of the solution adjusted to 7.0 by the addition of citric acid.
  • photographic elements containing a photographic silver halide emulsion layer can be treated with other ultraviolet absorbing compounds embraced by Formula I above.
  • the accompanying drawing illustrates schematically a cross-sectional View of a photographic element containing a layer having incorporated therein the sodium salt of 4 [3 (3 sulfobenzamido)benzoyl] 6 n hexylresorcinol, which is representative of the ultraviolet absorbing agents which can be employed in our invention.
  • a support 10 of any suitable material, such as cellulose acetate, or paper, having thereon an emulsionlayer 11 is coated with a iilter layer 12 having incorporated therein the sodium salt of 4 [3 (3 sulfobenzamido)benzoyl] 6 n hexylrescorcinol, or some other ultraviolet absorbing compound selected from those represented by the above general Formula I.
  • a support 10 of any suitable material such as cellulose acetate, or paper, having thereon an emulsionlayer 11 is coated with a iilter layer 12 having incorporated therein the sodium salt of 4 [3 (3 sulfobenzamido)benzoyl] 6 n hexylrescorcinol, or some other ultraviolet absorbing compound selected from those represented by the above general Formula I.
  • the drawing is merely representative of other structures which can be employed in our invention, and that the element can have other layers, not shown, such as additional light-sensitive layers, subbing layers, antihalation layers, etc.
  • the water-soluble ultraviolet absorbing compounds of our invention into the photographic element by simply bathing the element in an'aqueous solution containing the ultraviolet absorbing cornpound. 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.
  • the photographic 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 material used in absorbing the ultraviolet radiation can be incorporated directly in the light-sensitive emulsion instead of, or in addition to, being present in a separate filter layer. Generally, it is more advantageous to incorporate such ultraviolet absorbing compounds in a separate lter layer, however.
  • a photographic element comprising a support, at least one photographic silver halide emulsion layer, and incorporated in one of the layers of said photographic element a compound selected from those represented by the following general formula:
  • R represents a member selected from the group consisting of an alkyl group and an alkoxyl group
  • R1 represents an organic group selected from the group consisting of an aryl group and an aryloxymethyl group, said organic group being substituted by a radical selected from the group consisting of a sulfo group, a carboxyl group and an alkali metal salt of said radicals.
  • a photographic element comprising a support, at least one photographic gelatino-silver halide emulsion layer, and incorporated in one of the layers of said photographic element a compound selected from those represented by the following general formula:
  • R represents a member selected from the group consisting of an alkyl group containing from 1 to 12 carbon atoms and an alkoxyl group containing from 1 to 2 carbon atoms
  • R1 represents an organic group selected from the group consisting of a monocyclic aryl group and a monocyclic aryloxymethyl group, said organic group being substituted by a radical selected from the group consisting of a sulfo group, a carboxyl group and an alkali metal salt of said radicals.
  • 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 represents a member selected from the group consisting of an alkyl group containing from 1 to 12 carbon atoms and an alkoxyl group containing from 1 to 2 carbon atoms
  • R1 represents an organic group selected from the group consisting of a monocyclic aryl group and a monocyclic aryloxymethyl group, said organic group being substituted by a radical selected from the group consisting of a sulfo group, a carboxyl group and an alkali metal salt of said radicals.
  • a linished photographic element comprising a support having thereon a plurality of developed and fixed photographic emulsion layers containing coupled-dye images, atleast 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 support and a gelatin layei containing an ultraviolet absorbing compound selected from those represented by the following general formula:
  • a photographic element comprising a support, a photographic gelatino-silver halide emulsion layer, and a gelatin layer containing the sodium salt of a compound having the following formula:
  • a method of preventing image degradation in a nished photographic element comprising a plurality of developed and xed 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 support and a gelatin outer layer, which comprises applying to said photographic element from aqueous, non-colloidal solution an ultraviolet radiation absorbing compound selected from those represented by the following general formula:
  • R represents a member selected from the group consisting of an alkyl group and an alkoxyl group
  • R1 represents an organic group selected from the group consisting of an aryl group and an aryloxymethyl group, said organic group being substituted by a radical selected from the group consisting of a sulfo group, a carboxyl group and an alkali metal salt of said radicals.
  • a process of incorporating an ultraviolet absorbing compound into a photographic element comprising bathing said photographic element in an aqueous, non-colloidal solution of a compound selected from those represented by the following general formula:
  • R represents a member selected from the group consisting of an alkyl group and an alkoxyl group
  • R1 represents an organic group selected from the group consisting of an aryl group and an aryloxymethyl group, said organic group being substituted by a radical selected from the group consisting of a sulfo group, a carboxyl group and an alkali metal salt of said radicals
  • said photographic element comprising a support, at least one photographic silver halide emulsion layer, and an outer gelatin layer.

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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)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
US317904A 1952-10-31 1952-10-31 Photographic element Expired - Lifetime US2719086A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
BE523922D BE523922A (enrdf_load_stackoverflow) 1952-10-31
US317904A US2719086A (en) 1952-10-31 1952-10-31 Photographic element
DEE7989A DE964654C (de) 1952-10-31 1953-10-21 Photographisches Material mit einer ultraviolettabsorbierenden Schicht
GB30108/53A GB745704A (en) 1952-10-31 1953-10-30 Ultraviolet radiation absorbing compounds and photographic elements containing such compounds
FR1102962D FR1102962A (fr) 1952-10-31 1953-10-30 Nouveaux composés de résorcine, leur application, notamment en photographie, pour la protection contre l'ultra-violet et nouveaux produits obtenus
US408576A US2756253A (en) 1952-10-31 1954-02-05 Aroyl resorcinol compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US317904A US2719086A (en) 1952-10-31 1952-10-31 Photographic element

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US2719086A true US2719086A (en) 1955-09-27

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US317904A Expired - Lifetime US2719086A (en) 1952-10-31 1952-10-31 Photographic element

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US (1) US2719086A (enrdf_load_stackoverflow)
BE (1) BE523922A (enrdf_load_stackoverflow)
DE (1) DE964654C (enrdf_load_stackoverflow)
FR (1) FR1102962A (enrdf_load_stackoverflow)
GB (1) GB745704A (enrdf_load_stackoverflow)

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3057921A (en) * 1959-06-11 1962-10-09 American Cyanamid Co Aminohydroxybenzophenones and triazine derivatives thereof
US3060029A (en) * 1960-09-12 1962-10-23 Gen Aniline & Film Corp Photographic ultraviolet absorbers
US3131062A (en) * 1960-01-27 1964-04-28 Miehle Goss Dexter Inc Triphenyl leucocyanide sensitive compositions and elements
US3214463A (en) * 1960-05-12 1965-10-26 Du Pont Uv-absorbing sulfonated benzophenone derivatives
US3215530A (en) * 1960-11-16 1965-11-02 Agfa Ag Color photographic element protected against fading and method of applying protective film thereto
US3322555A (en) * 1962-05-02 1967-05-30 Agfa Ag Water-insoluble protective coatings for photographic materials
US3352673A (en) * 1963-10-28 1967-11-14 Eastman Kodak Co Multilayer color photographic element
EP1571181A2 (en) 2004-02-24 2005-09-07 Fuji Photo Film Co., Ltd. Inorganic fine particle dispersion and manufacturing method thereof as well as image-recording material
EP1612054A1 (en) 2004-07-02 2006-01-04 Fuji Photo Film Co., Ltd. Inkjet recording medium
EP1764796A2 (en) 2005-09-07 2007-03-21 FUJIFILM Corporation Optical recording medium and production method thereof
EP1768119A2 (en) 2005-08-25 2007-03-28 FUJIFILM Corporation Optical information recording medium, optical information recording method and optical information reproducing method
EP1974941A1 (en) 2007-03-29 2008-10-01 FUJIFILM Corporation Image-forming method using heat-sensitive transfer system
EP1974948A2 (en) 2007-03-29 2008-10-01 FUJIFILM Corporation Image-forming method using heat-sensitive transfer system
EP1980409A2 (en) 2007-03-29 2008-10-15 FUJIFILM Corporation Heat-sensitive transfer sheet for use in heat-sensitive transfer system and image-forming method using heat-sensitive transfer system
EP1985457A2 (en) 2007-04-25 2008-10-29 FUJIFILM Corporation Cardboard cylinder for a heat-sensitive transfer image-receiving sheet, rolled heat-sensitive transfer image-receiving sheet to form a roll shape, and image-forming method
EP2020304A1 (en) 2007-08-03 2009-02-04 FUJIFILM Corporation Ink jet recording medium
EP2055496A2 (en) 2007-11-01 2009-05-06 Fujifilm Corporation Inkjet recording material
WO2010013529A1 (ja) 2008-07-30 2010-02-04 富士フイルム株式会社 インクジェット記録方法
WO2010013582A1 (ja) 2008-07-30 2010-02-04 富士フイルム株式会社 インクジェット記録方法
WO2010090213A1 (ja) 2009-02-04 2010-08-12 富士フイルム株式会社 熱分布表示体及び熱分布確認方法
WO2012015076A1 (en) 2010-07-29 2012-02-02 Fujifilm Corporation Polymerizable composition
EP2436740A1 (en) 2003-09-29 2012-04-04 Fujifilm Corporation Ink for inkjet printing, ink set for inkjet printing, inkjet recording material and producing method for inkjet recording material, and inkjet recording method
WO2014124052A1 (en) 2013-02-06 2014-08-14 Fujifilm Hunt Chemicals, Inc. Chemical coating for a laser-markable material

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE623419A (enrdf_load_stackoverflow) * 1961-10-10

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1915429A (en) * 1929-01-31 1933-06-27 Gen Aniline Works Inc Para-hydroxy-diarylamine-carboxylic acids and process of making same
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
US2389147A (en) * 1943-11-20 1945-11-20 Ernst A H Friedhelm 4' methoxy 5 halogeno diphenylamino 2' carboxyl compound and process for producing the same

Family Cites Families (8)

* 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 (enrdf_load_stackoverflow) * 1935-04-05
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
GB524320A (en) * 1939-01-23 1940-08-05 Kodak Ltd Photographic elements having short-wave light absorbing filters
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 (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1915429A (en) * 1929-01-31 1933-06-27 Gen Aniline Works Inc Para-hydroxy-diarylamine-carboxylic acids and process of making same
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
US2389147A (en) * 1943-11-20 1945-11-20 Ernst A H Friedhelm 4' methoxy 5 halogeno diphenylamino 2' carboxyl compound and process for producing the same

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3057921A (en) * 1959-06-11 1962-10-09 American Cyanamid Co Aminohydroxybenzophenones and triazine derivatives thereof
US3131062A (en) * 1960-01-27 1964-04-28 Miehle Goss Dexter Inc Triphenyl leucocyanide sensitive compositions and elements
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
US3215530A (en) * 1960-11-16 1965-11-02 Agfa Ag Color photographic element protected against fading and method of applying protective film thereto
US3322555A (en) * 1962-05-02 1967-05-30 Agfa Ag Water-insoluble protective coatings for photographic materials
US3352673A (en) * 1963-10-28 1967-11-14 Eastman Kodak Co Multilayer color photographic element
EP2436740A1 (en) 2003-09-29 2012-04-04 Fujifilm Corporation Ink for inkjet printing, ink set for inkjet printing, inkjet recording material and producing method for inkjet recording material, and inkjet recording method
EP1571181A2 (en) 2004-02-24 2005-09-07 Fuji Photo Film Co., Ltd. Inorganic fine particle dispersion and manufacturing method thereof as well as image-recording material
EP2130876A1 (en) 2004-02-24 2009-12-09 FUJIFILM Corporation Inorganic fine particle dispersion and manufacturing method thereof as well as image-recording material
EP1612054A1 (en) 2004-07-02 2006-01-04 Fuji Photo Film Co., Ltd. Inkjet recording medium
EP1768119A2 (en) 2005-08-25 2007-03-28 FUJIFILM Corporation Optical information recording medium, optical information recording method and optical information reproducing method
EP1764796A2 (en) 2005-09-07 2007-03-21 FUJIFILM Corporation Optical recording medium and production method thereof
EP1974948A2 (en) 2007-03-29 2008-10-01 FUJIFILM Corporation Image-forming method using heat-sensitive transfer system
EP1980409A2 (en) 2007-03-29 2008-10-15 FUJIFILM Corporation Heat-sensitive transfer sheet for use in heat-sensitive transfer system and image-forming method using heat-sensitive transfer system
EP1974941A1 (en) 2007-03-29 2008-10-01 FUJIFILM Corporation Image-forming method using heat-sensitive transfer system
EP1985457A2 (en) 2007-04-25 2008-10-29 FUJIFILM Corporation Cardboard cylinder for a heat-sensitive transfer image-receiving sheet, rolled heat-sensitive transfer image-receiving sheet to form a roll shape, and image-forming method
EP2020304A1 (en) 2007-08-03 2009-02-04 FUJIFILM Corporation Ink jet recording medium
EP2055496A2 (en) 2007-11-01 2009-05-06 Fujifilm Corporation Inkjet recording material
WO2010013529A1 (ja) 2008-07-30 2010-02-04 富士フイルム株式会社 インクジェット記録方法
WO2010013582A1 (ja) 2008-07-30 2010-02-04 富士フイルム株式会社 インクジェット記録方法
WO2010090213A1 (ja) 2009-02-04 2010-08-12 富士フイルム株式会社 熱分布表示体及び熱分布確認方法
WO2012015076A1 (en) 2010-07-29 2012-02-02 Fujifilm Corporation Polymerizable composition
WO2014124052A1 (en) 2013-02-06 2014-08-14 Fujifilm Hunt Chemicals, Inc. Chemical coating for a laser-markable material

Also Published As

Publication number Publication date
FR1102962A (fr) 1955-10-27
DE964654C (de) 1957-05-23
BE523922A (enrdf_load_stackoverflow)
GB745704A (en) 1956-02-29

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