EP0766129A1 - Matériau photographique - Google Patents

Matériau photographique Download PDF

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Publication number
EP0766129A1
EP0766129A1 EP96114796A EP96114796A EP0766129A1 EP 0766129 A1 EP0766129 A1 EP 0766129A1 EP 96114796 A EP96114796 A EP 96114796A EP 96114796 A EP96114796 A EP 96114796A EP 0766129 A1 EP0766129 A1 EP 0766129A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
aryl
alkoxy
acyl
aryloxy
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.)
Withdrawn
Application number
EP96114796A
Other languages
German (de)
English (en)
Inventor
Beate Dr. Weber
Jörg Dr. Hagemann
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 EP0766129A1 publication Critical patent/EP0766129A1/fr
Withdrawn legal-status Critical Current

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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
    • G03C7/305—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers
    • G03C7/30511—Substances liberating photographically active agents, e.g. development-inhibiting releasing couplers characterised by the releasing group
    • 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
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/04—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances
    • 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
    • G03C7/396—Macromolecular additives
    • 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
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives

Definitions

  • the invention relates to a photographic material which contains photographically active compounds (PUG) covalently bound to a specific polymer and can thus be produced with thinner layers.
  • PAG photographically active compounds
  • polysiloxanes according to EP 555 923 are used as an additive to the oil phase in which, for example, a color coupler is dissolved or dispersed, improved phase stability against crystallization is achieved, but there are other disadvantages.
  • the dye stability of the dye formed from the coupler is insufficient.
  • Examples of the rest -L-PUG are: - (CH 2 ) 3 -O-PUG, - (CH 2 ) 3 -OCO-PUG, - (CH 2 ) 3 -O-CH 2 -CH 2 -OCO-PUG, - (CH 2 ) 3 -OCO-CH 2 -CH 2 -PUG, - (CH 2 ) 3 -OCO-CH 2 -CH 2 -COO-PUG and - (CH 2 ) 3 -OCO- (CH 2 ) 4 -CONH-PUG.
  • R 1 examples are: -H, -Si (CH 3 ) 3 , -CH 2 -CH 2 -CH 2 -COOH, - (CH 2 -CH 2 -O) 6 -CH 3 .
  • R 5 examples are: -OH, -OSi (CH 3 ) 3 , -O- (CH 2 ) 3 -COOH, -O- (CH 2 -CH 2 -O) 6 -CH 3 .
  • the compounds of formula (I) can contain one or more different groups PUG in one molecule.
  • Alkyl radicals can be straight-chain, branched or cyclic and optionally substituted.
  • Aryl radicals can be substituted.
  • Acyl residues are derived from aliphatic, olefinic, aromatic or heterocyclic carboxylic, carbonic, carbamic, sulfonic, amidosulfonic, phosphoric or phosphonic acids.
  • the compounds of the formulas (II) to (XVI) are linked via one of their substituents and the group L to the polysiloxane skeleton.
  • the compounds of the formula (I) according to the invention can be prepared by the process described in EP 480 466 or by known polymer-analogous processes.
  • n and m in the case of open-chain compounds of the formula (I) is in particular 4 to 50, preferably 4 to 30, in the case of cyclic compounds 3 to 7.
  • Examples of compounds according to the invention are those of the formulas below, where indicates that the groups in parentheses correspond to the molecular weight M ⁇ g (weight average) occur frequently. If two or more different monomers are used, the polymer structure is statistical.
  • the compound of formula (I) is used in the at least one layer, preferably in an amount of 0.001 to 5 g / m 2 material, in particular 0.001 to 2 g / m 2 material.
  • the compound of formula (I) is added as a solution or dispersion, e.g. as a solution in ethyl acetate, as a casting solution for the layer in question.
  • the photographic material can be a black and white material or a color photographic material.
  • color photographic materials are color negative films, color reversal films, color positive films, color photographic paper, color reversal photographic paper, color sensitive materials for the color diffusion transfer process or the silver color bleaching process.
  • the photographic materials consist of a support on which at least one light-sensitive silver halide emulsion layer is applied. Thin films and foils are particularly suitable as supports. An overview of carrier materials and auxiliary layers applied to their front and back is shown in Research Disclosure 37254, Part 1 (1995), p. 285.
  • the color photographic materials usually contain at least one red-sensitive, green-sensitive and blue-sensitive silver halide emulsion layer and, if appropriate, intermediate layers and protective layers.
  • these layers can be arranged differently. This is shown for the most important products:
  • Color photographic films such as color negative films and color reversal films have 2 or 3 red-sensitive, cyan-coupling silver halide emulsion layers, 2 or 3 green-sensitive, purple-coupling silver halide emulsion layers and 2 or 3 blue-sensitive, yellow-coupling silver halide emulsion layers on the carrier in the order given below.
  • the layers of the same spectral sensitivity differ in their photographic sensitivity, the less sensitive sub-layers generally being arranged closer to the support than the more sensitive sub-layers.
  • a yellow filter layer is usually applied between the green-sensitive and blue-sensitive layers, which prevents blue light from reaching the layers below.
  • Color photographic paper which is generally much less sensitive to light than a color photographic film, usually has a blue-sensitive, yellow-coupling silver halide emulsion layer, a green-sensitive, purple-coupling silver halide emulsion layer and a red-sensitive, cyan-coupling silver halide emulsion layer on the support in the order given below; the yellow filter layer can be omitted.
  • Deviations in the number and arrangement of the photosensitive layers can be carried out in order to achieve certain results. For example, all highly sensitive layers can be combined in one layer package and all low-sensitivity layers can be combined in another layer package in a photographic film in order to increase the sensitivity (DE 25 30 645).
  • Binding agents, silver halide grains and color couplers are essential components of the photographic emulsion layers.
  • Photographic materials with camera sensitivity usually contain silver bromoiodide emulsions, which may also contain small amounts of silver chloride.
  • Photographic copying materials contain either silver chloride bromide emulsions with up to 80 mol% AgBr or silver chloride bromide emulsions with over 95 mol% AgCl.
  • the maximum absorption of the dyes formed from the couplers and the color developer oxidation product is preferably in the following ranges: yellow couplers 430 to 460 nm, purple couplers 540 to 560 nm, cyan couplers 630 to 700 nm.
  • hydrophobic color couplers but also other hydrophobic components of the layers, are usually dissolved or dispersed in high-boiling organic solvents. These solutions or dispersions are then emulsified in an aqueous binder solution (usually gelatin solution) and, after the layers have dried, are present as fine droplets (0.05 to 0.8 ⁇ m in diameter) in the layers.
  • aqueous binder solution usually gelatin solution
  • the non-light-sensitive intermediate layers which are generally arranged between layers of different spectral sensitivity, can contain agents which prevent undesired diffusion of developer oxidation products from one light-sensitive layer into another light-sensitive layer with different spectral sensitization.
  • Suitable compounds can be found in Research Disclosure 37254, Part 7 (1995), p. 292 and in Research Disclosure 37038, Part III (1995), p. 84.
  • the photographic material can also contain UV light-absorbing compounds, whiteners, spacers, filter dyes, formalin scavengers, light stabilizers, antioxidants, D min dyes, additives to improve the stability of dyes, couplers and whites as well as to reduce the color fog, plasticizers (latices), Contain biocides and others.
  • Suitable compounds can be found in Research Disclosure 37254, Part 8 (1995), p. 292 and in Research Disclosure 37038, Parts IV, V, VI, VII, X, XI and XIII (1995), p. 84 ff.
  • the layers of color photographic materials are usually hardened, i.e. the binder used, preferably gelatin, is crosslinked by suitable chemical processes.
  • Suitable hardener substances can be found in Research Disclosure 37254, Part 9 (1995), p. 294 and in Research Disclosure 37038, Part XII (1995), page 86.
  • Samples B to M are prepared and tested like sample A, with the difference that a photographic useful compound (PNV) has been added to the emulsifier and, if appropriate, couplers and coupler solvents have been replaced by the compounds shown in Table 1.
  • PNV photographic useful compound
  • a color photographic recording material suitable for a rapid processing process was produced by applying the following layers in the order given to a support made of paper coated on both sides with polyethylene.
  • the quantities given relate to 1 m 2 .
  • the corresponding amounts of AgNO 3 are given for the silver halide application.
  • Samples 2 to 9 were produced like sample 1 with the difference that the amount of a dye stabilizer indicated in Table 2.1 was additionally added to layer 2 and the corresponding amount of coupler solvent OF-3 was omitted.
  • the compounds according to the invention are very good dark storage stabilizers (comparison with known yellow dye stabilizers ST-7, ST-8 and ST-9) and can also be advantageously combined with other dye stabilizers.
  • the siloxane ST-10 without a photographically useful group according to the invention is practically without a stabilizing effect.
  • Samples 10 to 24 are produced like sample 1, with the difference that in layer 4 the dye stabilizers ST-4 and ST-5 are replaced by those given in table 3.
  • the purple coupler M-2 is also replaced by 0.13 g of the purple coupler M-3 and 0.48 g M-4. In the latter case, the silver order is increased by 60%.
  • the compounds according to the invention are very good light stabilizers for pp couplers (comparison with known purple dye stabilizers ST-4, ST-11, ST-12 and ST-13) and can also be combined well with one another.
  • Samples II to IX are produced like sample I, with the difference that the UV absorber UV-1 is replaced by the amount of another UV absorber specified in Table 4.
  • the oil former is also omitted for samples V to IX.
  • the compounds according to the invention give significantly more stable UV layers under tropical storage conditions.
  • Samples N to Y were produced like sample A with the difference that the coupler Y-1 was replaced by the same amount as the coupler shown in Table 5 and the oil former OF-1 was replaced by dibutyl phthalate.
  • Samples 25 and 26 are prepared like Sample 1, with the difference that the color couplers in layers 2 (gb), 4 (pp) and 6 (bg) are replaced by those given in Table 6.
  • sample 26 the amount of oil former in the respective layer was reduced by 50%.
  • the material is exposed through a step wedge each with a filter that is permeable to red, green and blue light, so that a cyan, purple and yellow color separation is obtained.
  • NK neutral wedges
  • FAZ color separation wedges
  • Samples 27 to 36 are prepared like sample 1, with the difference that in layer 3 and layer 5 TKP, SC-1 and 2,5-di-tert-octylhydroquinone are replaced by 0.08 g of that in table 7 specified connections. In addition, in layer 4 the purple coupler M-2 was exchanged for 0.24 g M-1.
  • the samples are exposed behind a graduated gray wedge through a filter that is transparent to green light and processed as described for sample 1.
  • the compounds according to the invention are as effective EOP scavengers as the comparative compounds SC-2 and SC-3 without, however, impairing the light stability of the purple dye.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
EP96114796A 1995-09-27 1996-09-16 Matériau photographique Withdrawn EP0766129A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19535939A DE19535939A1 (de) 1995-09-27 1995-09-27 Fotografisches Material
DE19535939 1995-09-27

Publications (1)

Publication Number Publication Date
EP0766129A1 true EP0766129A1 (fr) 1997-04-02

Family

ID=7773326

Family Applications (1)

Application Number Title Priority Date Filing Date
EP96114796A Withdrawn EP0766129A1 (fr) 1995-09-27 1996-09-16 Matériau photographique

Country Status (4)

Country Link
US (1) US5726004A (fr)
EP (1) EP0766129A1 (fr)
JP (1) JPH09114059A (fr)
DE (1) DE19535939A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2800073A1 (fr) * 1999-10-26 2001-04-27 Oreal Nouveaux composes silicies derives de l'acide ascorbique, procede de preparation, compositions les comprenant et utilisations

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006032741A1 (fr) * 2004-09-20 2006-03-30 L'oréal Derives silicies de sulfone merocyanine ; compositions photoprotectrices les contenant ; utilisation comme filtre uv
GB2445635A (en) * 2006-10-13 2008-07-16 Ciba Sc Holding Ag Merocyanine derivatives useful as UV absorbers
JP5640471B2 (ja) * 2010-06-02 2014-12-17 Jsr株式会社 液晶配向剤、液晶配向膜、液晶配向膜の形成方法及び液晶表示素子
CN115925878A (zh) 2015-06-05 2023-04-07 艾比欧公司 用于治疗纤维化的内皮抑素片段和变体

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2504025A1 (de) * 1974-02-01 1975-08-07 Fuji Photo Film Co Ltd Photographisches lichtempfindliches material
EP0665233A2 (fr) * 1994-01-24 1995-08-02 Ciba-Geigy Ag Composés d'1-hydrocarbyloxy-pipéridine contenant des groupes de silane comme stabilisants de matériaux organiques

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1243409B (it) * 1990-12-17 1994-06-10 Ciba Geigy Spa Composti piperidinici contenenti gruppi silenici atti all'impiego come stabilizzanti per materiali organici
IT1271131B (it) * 1994-11-30 1997-05-26 Ciba Geigy Spa Composti piperidinici contenenti gruppi silanici come stabilizzanti per materiali organici

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2504025A1 (de) * 1974-02-01 1975-08-07 Fuji Photo Film Co Ltd Photographisches lichtempfindliches material
EP0665233A2 (fr) * 1994-01-24 1995-08-02 Ciba-Geigy Ag Composés d'1-hydrocarbyloxy-pipéridine contenant des groupes de silane comme stabilisants de matériaux organiques

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2800073A1 (fr) * 1999-10-26 2001-04-27 Oreal Nouveaux composes silicies derives de l'acide ascorbique, procede de preparation, compositions les comprenant et utilisations
WO2001030784A1 (fr) * 1999-10-26 2001-05-03 L'oreal Composes silicies derives de l'acide ascorbique
RU2221804C1 (ru) * 1999-10-26 2004-01-20 Л'Ореаль Кремнийсодержащие производные аскорбиновой кислоты
US6780888B1 (en) 1999-10-26 2004-08-24 L'oreal S.A. Silicon compounds derived from ascorbic acid

Also Published As

Publication number Publication date
JPH09114059A (ja) 1997-05-02
DE19535939A1 (de) 1997-04-03
US5726004A (en) 1998-03-10

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