EP0176845A2 - Matériau d'enregistrement photographique - Google Patents

Matériau d'enregistrement photographique Download PDF

Info

Publication number
EP0176845A2
EP0176845A2 EP85111669A EP85111669A EP0176845A2 EP 0176845 A2 EP0176845 A2 EP 0176845A2 EP 85111669 A EP85111669 A EP 85111669A EP 85111669 A EP85111669 A EP 85111669A EP 0176845 A2 EP0176845 A2 EP 0176845A2
Authority
EP
European Patent Office
Prior art keywords
alkyl
color
couplers
oder
coupler
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.)
Granted
Application number
EP85111669A
Other languages
German (de)
English (en)
Other versions
EP0176845A3 (en
EP0176845B1 (fr
Inventor
Günter Dr. Renner
Werner Dr. Liebe
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.)
Agfa Gevaert AG
Original Assignee
Agfa Gevaert AG
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
Application filed by Agfa Gevaert AG filed Critical Agfa Gevaert AG
Publication of EP0176845A2 publication Critical patent/EP0176845A2/fr
Publication of EP0176845A3 publication Critical patent/EP0176845A3/de
Application granted granted Critical
Publication of EP0176845B1 publication Critical patent/EP0176845B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/392—Additives
    • G03C7/39208—Organic compounds
    • G03C7/39212—Carbocyclic
    • G03C7/39216—Carbocyclic with OH groups

Definitions

  • the invention relates to a photographic recording material with at least one silver halide emulsion layer, which contains novel light stabilizers for the image dyes produced during chromogenic development, in particular for yellow or pupil-colored azomethine dyes.
  • color photographic images by chromogenic development, i.e. by developing imagewise exposed silver halide emulsion layers in the presence of suitable color couplers by means of suitable color-forming developer substances - so-called color developers - the oxidation product of the developer substances which is produced in accordance with the silver image reacting with the color coupler to form a dye image.
  • color developers i.e. by developing imagewise exposed silver halide emulsion layers in the presence of suitable color couplers by means of suitable color-forming developer substances - so-called color developers - the oxidation product of the developer substances which is produced in accordance with the silver image reacting with the color coupler to form a dye image.
  • Aromatic compounds containing primary amino groups in particular those of the p-phenylenediamine type, are usually used as color developers.
  • Suitable light-stabilizing agents are essentially phenolic compounds, in particular derivatives of hydroquinone, which are either added to the couplers or linked to the coupler molecules in the form of substituents (DE-B-1 547 803, DE-A-26 17 826, DE-A -29 52 511, JP-N 53 070 822, JP-N 54 070 830, JP-N 54 073 032).
  • the invention is based on the object of specifying novel light stabilizers for photographic recording materials, in particular those which are suitable for improving the light stability of the yellow image dyes produced from yellow couplers.
  • group G is either a hydroxyl group or an alkali-labile precursor group of a hydroxyl group.
  • An alkali-labile precursor group of a hydroxyl group means a group which undergoes a conversion under the conditions of alkaline development and thereby forms a hydroxyl group.
  • Typical examples of this are "acylated hydroxyl groups" which are hydrolyzed by alkali during development, the blocking acyl group being split off.
  • Blocking acyl groups are derived, for example, from aliphatic or aromatic carboxylic or sulfonic acids; Examples include acetyl, dichloroacetyl, alkoxycarbonyl, pyruvoyl.
  • the radical which cannot be split off under the conditions of chromogenic development and is represented by X can be, for example, an alkyl, alkoxycarbonyl, carbamoyl, acylamino, sulamoyl, alkylsulfonyl or arylsulfonyl radical.
  • Particularly suitable are those residues which not only do not cleave under the conditions of chromogenic development, that is to say at pH values between 9 and 12, but which also do not give the light-stabilizing compound oxidizability under these conditions (for example as a result of subsequent products from development).
  • alkyl radicals mentioned can be straight-chain or branched and contain up to 18 carbon atoms or more; Examples are methyl, ethyl, t-butyl, 1,1,3,3-tetramethylbutyl, n-dodecyl or n-tridecyl. Such alkyl radicals can also be found in the alkoxycarbonyl, Carbamoyl, acylamino, sulfamoyl and alkylsulfonyl radicals may be included.
  • the alkyl radicals represented by R 1 , R 2 or Z can be straight-chain or branched and can contain up to 20 C atoms and optionally further substituents.
  • substituents are, for example, phenoxy groups, which in turn can be further substituted by alkyl, alkoxy, hydroxyl or halogen.
  • An aralkyl radical represented by R 2 is, for example, benzyl; an aryl group represented by R 2 is, for example, phenyl.
  • An alkoxy or alkylamino radical represented by R 3 can contain a straight-chain or branched, optionally substituted alkyl radical having up to 20 carbon atoms.
  • An arylamino radical represented by R 3 is, for example, an anilino radical which may contain further substituents, such as halogen, nitro or alkyl.
  • a halogen substituent represented by Z is, for example, chlorine or bromine.
  • An acylamino group represented by Z is derived from aliphatic or aromatic carboxylic or sulfonic acids.
  • the group t-CSH17 in the compounds S-20 to S-23 is an alkyl radical of the following structure
  • the compounds of formula I to be used according to the invention can be prepared by known methods, e.g. B. by acylation or sulfonation of the corresponding o-aminophenols, in dipolar aprotic solvents such as dimethylformamide, dimethylacetamide, hexamethylphosphoric acid triamide, N-methylpyrolidone or the like or in dipolar solvents such as acetone, methyl ethyl ketone, acetonitrile or in protic solvents such as alcohols with base addition.
  • dipolar aprotic solvents such as dimethylformamide, dimethylacetamide, hexamethylphosphoric acid triamide, N-methylpyrolidone or the like
  • dipolar solvents such as acetone, methyl ethyl ketone, acetonitrile
  • protic solvents such as alcohols with base addition.
  • the color photographic recording materials according to the invention are preferably multilayer materials which have a plurality of silver halide emulsion layers or emulsion layer units with different spectral sensitivity.
  • Emulsion layer units are understood to mean laminates of 2 or more silver halide emulsion layers of the same spectral sensitivity.
  • Each of the light-sensitive silver halide emulsion layers or emulsion layer units mentioned is assigned a color coupler which can react with color developer oxidation products to form a non-diffusing dye.
  • the color couplers are expediently non-diffusing and accommodated in the light-sensitive layer itself or in close proximity to it.
  • the color couplers assigned to the two or more partial layers of an emulsion layer unit do not necessarily have to be identical. They are only intended to give the same color in color development, usually a color that is complementary to the color of the light to which the photosensitive silver halide emulsion layers are sensitive.
  • the red-sensitive silver halide emulsion layers are consequently each assigned at least one non-diffusing color coupler for producing the blue-green partial color image, generally a coupler of the phenol or ⁇ -naphthol type.
  • a coupler of the phenol or ⁇ -naphthol type particularly cyan couplers as described in US-A-2,474,293, US-A-2,367,531, US-A-2,895,826, US-A-3,772,002, EP-AO 028 099, EP -AO 112 514.
  • the green-sensitive silver halide emulsion layers each contain at least one non-diffusing color coupler for producing the purple partial color image, color couplers of the 5-pyrazolone or indazolone type usually being used. Particularly noteworthy are, for example, purple couplers such as these are described in US-A-2 600 788, US-A-4 383 027, DE-A-1 547 803, DE-A-1 810 464, DE-A-2 408 665, DE-A-3 226 163 .
  • the blue-sensitive silver halide emulsion layers each contain at least one non-diffusing color coupler for producing the yellow partial color image, usually a color coupler with an open-chain ketomethylene grouping.
  • a color coupler with an open-chain ketomethylene grouping are particularly noteworthy.
  • yellow couplers as described in US-A-3 408 194, DE-A-2 329 587, DE-A-2 456 976.
  • Color couplers of these types are known in large numbers and are described in a large number of patents. Examples include the publications “Color Coupler” by W. Pelz, "Messages from the research laboratories of Agfa, Leverkusen / Kunststoff", Volume III (1961) p. 111 and K. Venkataraman in “The Chemistry of Synthetic Dyes", Vol. 4, 341 to 387, Academic Press (1971).
  • the color couplers can be either conventional 4-equivalent couplers or 2-equivalent couplers, in which a smaller amount of silver halide is required to produce the color.
  • 2-equivalent couplers are derived from the 4-equivalent couplers in that they contain a substituent in the coupling point which is split off during the coupling.
  • the 2-equivalent couplers which can be used according to the present invention include both those which are practical are colorless as well as those that have an intense intrinsic color that disappears when the color is coupled or is replaced by the color of the image dye produced.
  • the latter couplers can also be present in the light-sensitive silver halide emulsion layers and serve there as mask couplers to compensate for the undesired secondary densities of the image dyes.
  • the 2-equivalent couplers include the known DIR couplers, which are couplers that contain a detachable residue in the coupling point, which is released as a diffusible development inhibitor or precursor of a development inhibitor when reacted with color developer oxidation products.
  • color coupler mixtures can be used to set a desired color or reactivity.
  • water-soluble couplers can be used in combination with hydrophobic water-insoluble couplers.
  • the same methods that are also used for the incorporation of the compounds according to the invention are suitable for incorporating the couplers into the layers of the color photographic recording material.
  • one advantageously uses one of the known emulsifying processes for incorporating hydrophobic color couplers, in which, for example, the color coupler is optionally dissolved in an organic solvent in the presence of a high-boiling coupler solvent or oil former and then in a gelatin solution is dispersed.
  • high-boiling coupler solvents are dibutyl phthalate and tricresyl phosphate.
  • Other coupler solvents are described, for example, in US-A-2,322,927, US-A-3,689,271, US-A-3,764,336 and US-A-3,765,897.
  • aqueous dispersions of the hydrophobic couplers it is also possible to prepare aqueous dispersions of the hydrophobic couplers and to add them to the respective casting solutions.
  • aqueous slurries of the couplers are finely ground, for example by intensive stirring with the addition of sharp-edged sand and / or by using ultrasound.
  • the compounds according to the invention are preferably used together with yellow couplers; however, effects are also achieved when used in combination with magenta couplers or with cyan couplers.
  • they can be dissolved in an oil former together with the respective color couplers and added to the respective casting solution in the form of such a common solution.
  • they can also be added to the casting solution in the form of a separate solution in an oil former.
  • Advantageous results can be achieved if from 5 to 200% by weight, preferably 20 to 100% by weight, of the compound according to the invention, each based on the amount of the color coupler used, are used.
  • Compound I and the assigned color coupler are preferably in the same layer. However, it is also possible to introduce them into adjacent layers.
  • the color photographic recording material can additionally contain other known stabilizing agents, for example UV absorbers and agents which prevent or delay the fading of the dyes, in particular when exposed to light, heat or moisture.
  • stabilizing agents for example UV absorbers and agents which prevent or delay the fading of the dyes, in particular when exposed to light, heat or moisture.
  • UV absorbers for example, phenol derivatives, hydroquinone derivatives, p-alkoxyphenol derivatives, pyrogallol derivatives, gallic acid derivatives, 5-hydroxycoumaran derivatives, 6-hydroxychromane derivatives and 5-hydroxyindane derivatives have been described as being suitable for this purpose.
  • the compounds according to the invention are preferably used in combination with yellow couplers.
  • yellow couplers are in particular hydrophobic yellow couplers with good solubility in hydrophobic or hydrophilic oil formers.
  • the yellow couplers are preferably derived from ⁇ -pivaloyl or OC, benzoyl acetanilides. Examples of such yellow couplers are listed below.
  • the intermediate layers arranged between the light-sensitive silver halide emulsion layers, the binder of which preferably consists of gelatin, may contain compounds which are capable of reacting with color developer oxidation products and which thus prevent undesired diffusion of the color developer oxidation products.
  • examples of such compounds are non-diffusing reducing agents, e.g. Hydroquinone derivatives which, when reacted with the color developer oxidation products, do not give any dye remaining in the layers, or color couplers which give a soluble dye which is washed out of the layers during color photographic processing.
  • the recording materials according to the invention can be developed with the usual color developer compounds, in particular those of the p-phenylenediamine series with a primary amino group, for example 4-amino-N, N-dimethylaniline, 4-amino-N, N-diethylaniline, 4-amino-3-methyl -N, N-diethylaniline, 4-amino-3-methyl-N-methyl-N- (B- methylsulfonamidoethyl) aniline, 4-amino-N-ethyl-N- (B-hydroxyethyl) aniline, 4-amino-3-methyl-N-ethyl-N- (B-hydroxyethyl) aniline, 4-amino-3 -methyl-N-ethyl-N- (ß-methoxyethyl) aniline, 4-amino-3-methyl-N-ethyl-N- (ß-methylsulfonamidoethyl) aniline, 4-amino-
  • Color photographic materials were prepared as follows.
  • the emulsify produced under a is mixed with a silver halide emulsion which contains 8.2 g of silver in the form of silver halide, 9.2 g of gelatin and 0.04 g of sodium dodecylbenzenesulfonate.
  • the total volume is adjusted to 350 ml with water.
  • the casting solution prepared in this way is poured onto a layer of cellulose triacetate.
  • the material After drying, the material is exposed behind a step wedge and color developed as usual.
  • the processed samples are then covered with a UV protective film and irradiated in a Xenotest device to determine the light fastness (40% relative humidity; 25 ° C; 100,000 lx.h.).
  • the UV protective film was made as follows. A layer of 1.5 g of gelatin, 0.65 g of compound A (UV absorber) of the following formula was placed on a transparent cellulose triacetate film provided with an adhesive layer
  • Developer A contains 2-amino-5- (N-ethyl-N-methanesulfonamidoethylamino) toluene as a color developer.
  • Developer B contains 2-amino-5- (N-ethyl-N-hydroxyethylamino) toluene as a color developer. The results (percentage decrease in color density) are shown in Table 1.
  • Example 2 The procedure was as in Example 1.
  • the following compounds were also tested, which were known as light-stabilizing agents for the purple dyes produced from pyrazolone couplers.
  • Compound S-3 also has some stabilizing effect on the lightfastness of the magenta and cyan dyes. Naturally, this effect is comparatively small with the already more stable cyan dyes.
  • Curing is carried out by covering with a 10% strength aqueous solution of an instant hardening agent.
  • Recording material 1 is obtained.
  • Recording material 2 is also prepared in a corresponding manner, with the only difference that layer 1 additionally contains 0.22 compound S-3.
  • the yellow color parts obtained were measured and the levels of the densities 0.8 and 1.0 were marked.
  • the wedges were then run in a Xenotest device with a light quantity of 15. 10 6 lx.h irradiated. The marked steps were then measured again. The results are shown in the table.

Landscapes

  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP85111669A 1984-09-27 1985-09-16 Matériau d'enregistrement photographique Expired - Lifetime EP0176845B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19843435443 DE3435443A1 (de) 1984-09-27 1984-09-27 Fotografisches aufzeichnungsmaterial
DE3435443 1984-09-27

Publications (3)

Publication Number Publication Date
EP0176845A2 true EP0176845A2 (fr) 1986-04-09
EP0176845A3 EP0176845A3 (en) 1988-09-21
EP0176845B1 EP0176845B1 (fr) 1991-02-06

Family

ID=6246485

Family Applications (1)

Application Number Title Priority Date Filing Date
EP85111669A Expired - Lifetime EP0176845B1 (fr) 1984-09-27 1985-09-16 Matériau d'enregistrement photographique

Country Status (4)

Country Link
US (1) US4656125A (fr)
EP (1) EP0176845B1 (fr)
JP (1) JPH0713737B2 (fr)
DE (2) DE3435443A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991018323A1 (fr) * 1990-05-16 1991-11-28 Kodak Limited Matiere photographique comprenant une combinaison d'accouplement de formation d'image a colorant magenta
EP0563638A1 (fr) * 1992-03-23 1993-10-06 Agfa-Gevaert AG Matériau photographique d'enregistrement

Families Citing this family (82)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4745049A (en) * 1986-04-11 1988-05-17 Konishiroku Photo Industry Co., Ltd. Silver halide photographic light-sensitive material
DE3918547A1 (de) * 1989-06-07 1990-12-13 Agfa Gevaert Ag Farbfotografisches silberhalogenidmaterial
JPH04340960A (ja) * 1991-05-17 1992-11-27 Fuji Photo Film Co Ltd ハロゲン化銀カラー写真感光材料
US5491052A (en) * 1992-03-13 1996-02-13 Eastman Kodak Company Yellow layer for color photographic elements
JP2717489B2 (ja) * 1992-12-04 1998-02-18 富士写真フイルム株式会社 ハロゲン化銀カラー写真感光材料
JP2003094817A (ja) 2001-09-21 2003-04-03 Fuji Photo Film Co Ltd 感熱記録材料
US20070052783A1 (en) 2003-09-29 2007-03-08 Toshiki Taguchi Ink for inkjet printing ink set for inkjet printing inkjet recording material and producing method for inkjet recording material and inkjet recording method
EP1571181A3 (fr) 2004-02-24 2008-08-13 FUJIFILM Corporation Dispersion de particules inorganiques fines, sa méthode de préparation et matériau d'enregistrement d'image
JP4250121B2 (ja) 2004-07-02 2009-04-08 富士フイルム株式会社 インクジェット記録用媒体
US20060204732A1 (en) 2005-03-08 2006-09-14 Fuji Photo Film Co., Ltd. Ink composition, inkjet recording method, printed material, method of producing planographic printing plate, and planographic printing plate
JP4662822B2 (ja) 2005-07-19 2011-03-30 富士フイルム株式会社 光硬化型インクジェット記録装置
US20070049651A1 (en) 2005-08-23 2007-03-01 Fuji Photo Film Co., Ltd. Curable composition, ink composition, inkjet recording method, printed material, method of producing planographic printing plate, planographic printing plate, and oxcetane compound
JP4677306B2 (ja) 2005-08-23 2011-04-27 富士フイルム株式会社 活性エネルギー硬化型インクジェット記録装置
JP4757574B2 (ja) 2005-09-07 2011-08-24 富士フイルム株式会社 インク組成物、インクジェット記録方法、印刷物、平版印刷版の製造方法、及び、平版印刷版
EP2103639A1 (fr) 2005-11-04 2009-09-23 Fujifilm Corporation Composition a base d'epoxide polycyclique, encre et procede jet encre avec cela
EP1829684B1 (fr) 2006-03-03 2011-01-26 FUJIFILM Corporation Composition durcissable, composition d'encre, procédé d'enregistrement par jet d'encre et plaque d'impression planographique
JP4719606B2 (ja) 2006-03-30 2011-07-06 富士フイルム株式会社 インクジェットヘッド記録装置
JP5276264B2 (ja) 2006-07-03 2013-08-28 富士フイルム株式会社 インク組成物、インクジェット記録方法、印刷物、及び、平版印刷版の製造方法
US8038283B2 (en) 2007-01-18 2011-10-18 Fujifilm Corporation Ink-jet recording apparatus
JP2008189776A (ja) 2007-02-02 2008-08-21 Fujifilm Corp 活性放射線硬化型重合性組成物、インク組成物、インクジェット記録方法、印刷物、平版印刷版の作製方法、及び平版印刷版
JP5227521B2 (ja) 2007-02-26 2013-07-03 富士フイルム株式会社 インク組成物、インクジェット記録方法、印刷物、及び、インクセット
JP2008208266A (ja) 2007-02-27 2008-09-11 Fujifilm Corp インク組成物、インクジェット記録方法、印刷物、平版印刷版の製造方法、および平版印刷版
JP5224699B2 (ja) 2007-03-01 2013-07-03 富士フイルム株式会社 インク組成物、インクジェット記録方法、印刷物、平版印刷版の製造方法、及び平版印刷版
EP1970196A3 (fr) 2007-03-13 2010-01-27 FUJIFILM Corporation Élément hydrophile et son procédé de production
JP2008238711A (ja) 2007-03-28 2008-10-09 Fujifilm Corp 親水性部材及び下塗り組成物
JP2008246793A (ja) 2007-03-29 2008-10-16 Fujifilm Corp 活性エネルギー線硬化型インクジェット記録装置
JP5159141B2 (ja) 2007-03-30 2013-03-06 富士フイルム株式会社 インク組成物、インクジェット記録方法、印刷物、平版印刷版の作製方法及び平版印刷版
JP5337394B2 (ja) 2007-05-15 2013-11-06 富士フイルム株式会社 親水性コーティング組成物及びこれを用いた親水性部材
JP2009034942A (ja) 2007-08-03 2009-02-19 Fujifilm Corp インクジェット記録用媒体
JP2009256568A (ja) 2007-08-17 2009-11-05 Fujifilm Corp 親水性膜形成用組成物、スプレー用組成物およびこれを用いた親水性部材
JP5469837B2 (ja) 2007-09-12 2014-04-16 富士フイルム株式会社 親水性組成物
JP2009090641A (ja) 2007-09-20 2009-04-30 Fujifilm Corp 防曇性カバー、及び該防曇性カバーを用いたメーター用カバー
JP2009256564A (ja) 2007-09-26 2009-11-05 Fujifilm Corp 親水性膜形成用組成物および親水性部材
US8076393B2 (en) 2007-09-26 2011-12-13 Fujifilm Corporation Ink composition, inkjet recording method, and printed material
JP5111039B2 (ja) 2007-09-27 2012-12-26 富士フイルム株式会社 重合性化合物、重合開始剤、および染料を含有する光硬化性組成物
JP5236238B2 (ja) 2007-09-28 2013-07-17 富士フイルム株式会社 インクジェット記録用ホワイトインク組成物
JP5227560B2 (ja) 2007-09-28 2013-07-03 富士フイルム株式会社 インク組成物、インクジェット記録方法、印刷物、及び、成形印刷物の製造方法
JP2009090489A (ja) 2007-10-04 2009-04-30 Fujifilm Corp 画像形成方法及び画像形成装置
JP2009107319A (ja) 2007-11-01 2009-05-21 Fujifilm Corp インクジェット記録材料
US8240838B2 (en) 2007-11-29 2012-08-14 Fujifilm Corporation Ink composition for inkjet recording, inkjet recording method, and printed material
JP2009256571A (ja) 2008-01-25 2009-11-05 Fujifilm Corp 防かび作用を有する親水性組成物及び親水性部材
JP5124496B2 (ja) 2008-02-01 2013-01-23 富士フイルム株式会社 親水性部材
JP5591473B2 (ja) 2008-02-05 2014-09-17 富士フイルム株式会社 インク組成物、インクジェット記録方法、及び印刷物
JP5383225B2 (ja) 2008-02-06 2014-01-08 富士フイルム株式会社 インク組成物、インクジェット記録方法、および印刷物
JP5254632B2 (ja) 2008-02-07 2013-08-07 富士フイルム株式会社 インク組成物、インクジェット記録方法、印刷物、及び、成形印刷物
US20090214797A1 (en) 2008-02-25 2009-08-27 Fujifilm Corporation Inkjet ink composition, and inkjet recording method and printed material employing same
JP5427382B2 (ja) 2008-03-25 2014-02-26 富士フイルム株式会社 親水性部材、フィン材、アルミニウム製フィン材、熱交換器およびエアコン
JP4914862B2 (ja) 2008-03-26 2012-04-11 富士フイルム株式会社 インクジェット記録方法、及び、インクジェット記録装置
JP2009270062A (ja) 2008-05-09 2009-11-19 Fujifilm Corp 紫外線吸収剤組成物
JP2010030196A (ja) 2008-07-30 2010-02-12 Fujifilm Corp インクジェット記録方法
JP2010030223A (ja) 2008-07-30 2010-02-12 Fujifilm Corp インクジェット記録方法、インクジェット記録装置、及び、印刷物
JP2010030197A (ja) 2008-07-30 2010-02-12 Fujifilm Corp インクジェット記録方法
JP5383133B2 (ja) 2008-09-19 2014-01-08 富士フイルム株式会社 インク組成物、インクジェット記録方法及び印刷物成形体の製造方法
JP2010077228A (ja) 2008-09-25 2010-04-08 Fujifilm Corp インク組成物、インクジェット記録方法、及び、印刷物
EP2169018B1 (fr) 2008-09-26 2012-01-18 Fujifilm Corporation Composition d'encre et procédé d'enregistrement à jet d'encre
JP5461809B2 (ja) 2008-09-29 2014-04-02 富士フイルム株式会社 インク組成物、及び、インクジェット記録方法
JP5344892B2 (ja) 2008-11-27 2013-11-20 富士フイルム株式会社 インクジェット用インク組成物、及びインクジェット記録方法
JP5241564B2 (ja) 2009-02-27 2013-07-17 富士フイルム株式会社 活性放射線硬化型インクジェット記録用インク組成物、インクジェット記録方法、および印刷物
JP5225156B2 (ja) 2009-02-27 2013-07-03 富士フイルム株式会社 活性放射線硬化型インクジェット記録用インク組成物、インクジェット記録方法及び印刷物
JP2010202756A (ja) 2009-03-03 2010-09-16 Fujifilm Corp 活性エネルギー線硬化型インク組成物、インクジェット記録方法、及び印刷物
JP2010209183A (ja) 2009-03-09 2010-09-24 Fujifilm Corp インク組成物及びインクジェット記録方法
JP5349095B2 (ja) 2009-03-17 2013-11-20 富士フイルム株式会社 インク組成物、及び、インクジェット記録方法
JP5349097B2 (ja) 2009-03-19 2013-11-20 富士フイルム株式会社 インク組成物、インクジェット記録方法、印刷物、及び、成形印刷物の製造方法
JP2010229349A (ja) 2009-03-27 2010-10-14 Fujifilm Corp 活性エネルギー線硬化型組成物、活性エネルギー線硬化型インク組成物インク組成物及びインクジェット記録方法
JP5405174B2 (ja) 2009-03-30 2014-02-05 富士フイルム株式会社 インク組成物
JP5383289B2 (ja) 2009-03-31 2014-01-08 富士フイルム株式会社 インク組成物、インクジェット用であるインク組成物、インクジェット記録方法、およびインクジェット法による印刷物
JP5579533B2 (ja) 2009-08-27 2014-08-27 富士フイルム株式会社 新規なオキセタン化合物、活性エネルギー線硬化型組成物、活性エネルギー線硬化型インク組成物、及びインクジェット記録方法
JP5572026B2 (ja) 2009-09-18 2014-08-13 富士フイルム株式会社 インク組成物、及び、インクジェット記録方法
JP2011068783A (ja) 2009-09-25 2011-04-07 Fujifilm Corp インク組成物、及び、インクジェット記録方法
JP5489616B2 (ja) 2009-09-28 2014-05-14 富士フイルム株式会社 インク組成物及び印刷物成型体の製造方法
JP5554114B2 (ja) 2010-03-29 2014-07-23 富士フイルム株式会社 活性放射線硬化型インクジェット用インク組成物、印刷物、印刷物の製造方法、印刷物成形体、及び印刷物成形体の製造方法
US8573765B2 (en) 2010-03-31 2013-11-05 Fujifilm Corporation Active radiation curable ink composition, ink composition for inkjet recording, printed matter, and method of producing molded article of printed matter
JP5606817B2 (ja) 2010-07-27 2014-10-15 富士フイルム株式会社 活性放射線硬化型インクジェット用インク組成物、印刷物、印刷物成形体、及び印刷物の製造方法
EP3124557B1 (fr) 2011-02-28 2018-08-22 Fujifilm Corporation Composition d'encre et procédé de formation d'image
JP2012201874A (ja) 2011-03-28 2012-10-22 Fujifilm Corp インク組成物、及び画像形成方法
JP5756071B2 (ja) 2011-09-29 2015-07-29 富士フイルム株式会社 インクジェットインク組成物、及びインクジェット記録方法
JP5980702B2 (ja) 2013-03-07 2016-08-31 富士フイルム株式会社 インクジェットインク組成物、インクジェット記録方法、及び、成型印刷物の製造方法
JP5939644B2 (ja) 2013-08-30 2016-06-22 富士フイルム株式会社 画像形成方法、インモールド成型品の製造方法、及び、インクセット
JP6117072B2 (ja) 2013-09-30 2017-04-19 富士フイルム株式会社 顔料分散組成物、インクジェット記録方法、及び化合物の製造方法
JP6169545B2 (ja) 2014-09-09 2017-07-26 富士フイルム株式会社 重合性組成物、インクジェット記録用インク組成物、インクジェット記録方法、及び記録物
JP6086888B2 (ja) 2014-09-26 2017-03-01 富士フイルム株式会社 インクジェット記録用インク組成物、インクジェット記録方法、及び記録物
JP6169548B2 (ja) 2014-09-26 2017-07-26 富士フイルム株式会社 重合性組成物、インクジェット記録用インク組成物、インクジェット記録方法、及び記録物

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3519429A (en) * 1966-05-16 1970-07-07 Eastman Kodak Co Silver halide emulsions containing a stabilizer pyrazolone coupler
JPS5227534B1 (fr) * 1970-09-21 1977-07-21
JPS52147433A (en) * 1976-06-02 1977-12-07 Fuji Photo Film Co Ltd Color photographic light sensitive material
JPS52150630A (en) * 1976-06-09 1977-12-14 Mitsubishi Paper Mills Ltd Color photographic material containing stabilizer
JPS5724941A (en) * 1980-07-22 1982-02-09 Fuji Photo Film Co Ltd Color photographic sensitive material
JPS59192246A (ja) * 1983-04-15 1984-10-31 Fuji Photo Film Co Ltd カラ−写真感光材料
JPS59192247A (ja) * 1983-04-15 1984-10-31 Fuji Photo Film Co Ltd カラ−写真感光材料
JPS60108847A (ja) * 1983-11-18 1985-06-14 Konishiroku Photo Ind Co Ltd ハロゲン化銀カラ−写真感光材料
JPS60118836A (ja) * 1983-11-30 1985-06-26 Konishiroku Photo Ind Co Ltd ハロゲン化銀写真感光材料

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991018323A1 (fr) * 1990-05-16 1991-11-28 Kodak Limited Matiere photographique comprenant une combinaison d'accouplement de formation d'image a colorant magenta
US5552266A (en) * 1990-05-16 1996-09-03 Eastman Kodak Company Photographic material comprising a magenta dye image forming coupler combination
EP0563638A1 (fr) * 1992-03-23 1993-10-06 Agfa-Gevaert AG Matériau photographique d'enregistrement
US5340709A (en) * 1992-03-23 1994-08-23 Agfa-Gevaert Ag Photographic recording material

Also Published As

Publication number Publication date
EP0176845A3 (en) 1988-09-21
DE3435443A1 (de) 1986-04-03
US4656125A (en) 1987-04-07
JPH0713737B2 (ja) 1995-02-15
JPS6186750A (ja) 1986-05-02
EP0176845B1 (fr) 1991-02-06
DE3581686D1 (de) 1991-03-14

Similar Documents

Publication Publication Date Title
EP0176845B1 (fr) Matériau d'enregistrement photographique
DE3789277T2 (de) Lichtempfindliches photographisches Silberhalogenidmaterial, das einen gelben Kuppler enthält.
DE2329587C2 (de) Farbphotographisches Aufzeichnungsmaterial
EP0169458B1 (fr) Matériau d'enregistrement photographique couleur avec un coupleur DIR jaune
DE2841166C2 (de) Farbphotographische Silberhalogenidemulsion und deren Verwendung zur Erzeugung von Farbbildern
DE2934769A1 (de) Lichtempfindliches photographisches silberhalogenidmaterial und verfahren zur erzeugung von farbbildern
DE2706117C2 (fr)
DE3135938C2 (de) Photographisches Aufzeichnungsmaterial
DE3633364C3 (de) Farbfotografisches Aufzeichnungsmaterial mit einem Farbkuppler vom Pyrazoloazol-Typ
DE3021207A1 (de) Lichtempfindliches (farb)photographisches aufzeichnungsmaterial
EP0213490B1 (fr) Matériau d'enregistrement photographique couleur
DE2635492A1 (de) Photographischer farbkuppler
DE2754281A1 (de) Photographisches, lichtempfindliches silberhalogenid-material
EP0415056B1 (fr) Matériau d'enregistrement pour photographie en couleurs à un coupleur libérant un composé photographiquement actif
DE3026391C2 (fr)
DE3624544C2 (de) Farbfotografisches Aufzeichnungsmaterial mit einem Farbkuppler vom Pyrazoloazol-Typ
DE3622007C2 (de) Farbfotografisches Aufzeichnungsmaterial mit 2-Äquivalentpurpurkupplern
DE2705974C2 (fr)
DE3626219A1 (de) Farbfotografisches aufzeichnungsmaterial mit einem gelb-dir-kuppler
DE3625616A1 (de) Farbfotografisches aufzeichnungsmaterial mit 2-aequivalentpurpurkupplern
DE3878368T2 (de) Photographisches eintragungsmaterial mit einer ein purpurrotes farbbild bildenden kupplerverbindung.
DE2843954A1 (de) Lichtempfindliches frabphotographisches element
DE2454301A1 (de) Lichtempfindliches farbphotographisches material
DE3541858A1 (de) Farbfotografisches farbkupplerhaltiges aufzeichnungsmaterial
EP0217255B1 (fr) Matériau d'enregistrement photographique couleur avec des coupleurs formateurs de couleur faciles à disperser

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19850916

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): BE DE FR GB

RAP1 Party data changed (applicant data changed or rights of an application transferred)

Owner name: AGFA-GEVAERT AG

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): BE DE FR GB

17Q First examination report despatched

Effective date: 19890616

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): BE DE FR GB

REF Corresponds to:

Ref document number: 3581686

Country of ref document: DE

Date of ref document: 19910314

ET Fr: translation filed
GBT Gb: translation of ep patent filed (gb section 77(6)(a)/1977)
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 19960911

Year of fee payment: 12

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19970930

BERE Be: lapsed

Owner name: AGFA-GEVAERT A.G.

Effective date: 19970930

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 19990825

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19990830

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 19990910

Year of fee payment: 15

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20000916

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 20000916

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20010531

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20010601

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST