EP0093924B1 - Matériel d'enregistrement photographique - Google Patents
Matériel d'enregistrement photographique Download PDFInfo
- Publication number
- EP0093924B1 EP0093924B1 EP83103982A EP83103982A EP0093924B1 EP 0093924 B1 EP0093924 B1 EP 0093924B1 EP 83103982 A EP83103982 A EP 83103982A EP 83103982 A EP83103982 A EP 83103982A EP 0093924 B1 EP0093924 B1 EP 0093924B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- denotes
- group
- radical
- weight
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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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
- 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
- G03C1/053—Polymers obtained by reactions involving only carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/142—Dye mordant
Definitions
- the invention relates to a photographic recording material which contains crosslinked polymer latices in photographic light-sensitive and non-light-sensitive layers.
- Gelatin is generally used as a binder for photographic layers because of its advantageous properties as a protective colloid, as a dispersant and because of its chemical properties. Gelatin also has disadvantages as a photographic binder. So z. B. the insufficient dimensional stability under changing climatic conditions, d. H. at different temperatures and humidity levels that are inherent in the layers formed from it.
- a disadvantage of these polymers is that they increase the viscosity of the coating solutions when mixed with gelatin, especially when the crosslinking agents required for layer hardening are added to the coating solutions. With the dwell times of the casting solutions that occur during the coating process, this leads to an increase in viscosity which makes a defined layer application per unit area impossible. Furthermore, linear high molecular weight polyacrylamides in aqueous solutions are so viscous that processing such solutions is associated with considerable difficulties.
- the object of the invention is to provide crosslinked polymer latices which are not susceptible to hydrolysis, which do not impair the sensitometric properties of color photographic materials and which are compatible with the customary binders and which can be prepared in a simple manner.
- the crosslinked polymer latices of the invention can always be used in an advantageous manner when it is necessary to use a synthetic binder and to avoid the disadvantages of a strong increase in viscosity usually associated therewith.
- the structural unit characterized by the general formula represents the polymerized form of a low molecular weight carboxylic acid amide.
- Suitable monomeric carboxylic acid derivatives are those which are copolymerizable with the monomers M and V described below, such as. B. methacrylic acid, acrylic acid, crotonic acid, maleic acid or (vinylphenyl) acetic acid derivatives.
- Particularly advantageous monomers for the formation of the units V are trivinylcyclohexane, divinylbenzene, tetraallyloxyethane, 1,4-butylene dimethacrylate. Two or more of the monomers mentioned can also be used side by side to form units V of the polymers according to the invention.
- a wide variety of monoethylenically unsaturated monomers copolymerizable with the customary monomers can be used for the units M.
- Monomers with conjugated ethylenically unsaturated bonds are also suitable for this purpose.
- Typical suitable monomers N are: ethylene, propylene, 1-butene, 4-methylpentene-1, styrene, a-methylstyrene, monoethylenically unsaturated esters of aliphatic acids, e.g. B. vinyl acetate, isopropenylacetate, allyl acetate and the like; Esters of ethylenically unsaturated mono- and dicarboxylic acids, e.g. B.
- Water-soluble monomers such as, for. As acrylic acid, methacrylic acid, itaconic acid re. Maleic acid, acrylamido-2-methylpropanesulfonic acid, sulfoethyl methacrylate, N-vinylpyrrolidone.
- the grouping M can be formed not only from a single monomer, but also from various of the monomers mentioned.
- the latices according to the invention can be produced in various ways. According to a preferred production process, crosslinked polymer latices are used, which are converted into the polymeric amides in polymer-analogous reactions. Suitable starting compounds are e.g. B. crosslinked (meth) acrylic ester latexes, which react with amines to the polymeric amides according to the invention.
- the starting latices can in a known manner by emulsion copolymerization of monomeric polymerizable esters with polyfunctional monomers, such as. B. described in DE-A-26 52 464, are produced.
- monomeric esters are expediently used which have sufficient reactivity for the aminolysis to be carried out in the following stage.
- monomeric esters which are suitable for the preparation of the crosslinked starting latices are (meth) acrylic acid methyl ester, cyanomethyl (meth) acrylate, nitrophenyl (meth) acrylate, carbomethoxy methyi (meth) acrylate, carboethoxymethyl (meth) acrylate or chloromethyl (meth -) acrylate.
- Another production possibility is to start from crosslinked (meth) acrylic acid latices, as described in DE-A-26 52 464. In this case it is necessary to activate the carboxylic acid groups before the reaction with the amines. Ways to activate the carboxylic acid groups are known and z. B. described in Houben-Weyl, Volume 15/1 (1974), p. 28.
- the acid groups can also be activated by conversion into the acid halide or anhydride form.
- the reagents known from low-molecular chemistry are suitable, such as. B. thionyl chloride, phosphorus pentachloride, phosphorus trichloride or acetic anhydride.
- the crosslinked reactive starting latices are then reacted with amines to form the polymer latices according to the invention.
- the latices used as starting compounds can be present as aqueous dispersions. In those cases where the reactive starting latices can react with water, the starting latices are used as dispersions which contain organic, preferably polar, organic solvents as dispersants. It is often also expedient to use mixtures of water and organic solvent as dispersants.
- reaction conditions such as reaction time, temperature and the use of catalysts depend on the starting latex used.
- the reaction conditions can be chosen as they are known from the analogous reactions of linear uncrosslinked polymers or from low molecular weight chemistry. Descriptions of these possibilities can be found in Houben-Weyl, Volume 14/2 (1963), p. 738, Makromol. Chem., Rapid Connun. 1, 655 (1980), European Polymer Journal 15, 167 (1979), J. Polym. Sci. Chem. Ed. 12, 2453 (1974), J. Polym. Sci. Chem. Ed. 16, 1435 (1978), J. Polym. Sci. Chem. Ed. 12,553 (1974), Makromol. Chem. 175: 391 (1974), Makromol. Chem. 178, 2159 (1977) and Makromol. Chem. 181, 2495 (1980).
- Suitable amines are ammonia or alkylamines, e.g. B. methylamine, dimethylamine, ethylamine, propylamine, or butylamine, arylamines, e.g. B. aniline, 4-methylaniline or optionally substituted aminophenols, aralkylamines, e.g. B. optionally substituted butylamines, aminocarboxylic acids, for. B. lysine or glycine, alkylenediamines, e.g. B. diaminoethane, diaminohexane or hydroxyalkylamines, e.g. B. aminoethanol, alkoxyalkylamines, e.g. B. methoxyethylamine, amino ureas z. B. aminoethyl urea, secondary cyclic amines in which R 2 and R 3 represent a common radical, for. B. morpholine or piperdin.
- the particles of the latices of the invention generally have diameters from 20 nm to 1 ⁇ m and preferably 30 to 300 nm.
- the latices are coated with the binders customary in photographic materials, such as, for. B. gelatin, polyvinyl alcohol, carboxymethyl cellulose or hydroxyethyl cellulose compatible and form transparent layers in the mixture.
- the cleaning of the latices can be carried out by methods known to those skilled in the art, e.g. B. by flakes or redispersion, by dialysis, by ultrafiltration or by mixing with gelatin, pasta and water.
- the latices can be stabilized by wetting agents. Often, however, stabilization by adding wetting agents is not necessary, especially if the latices contain ionic groups such as carboxyl or sulfonyl groups or quaternary ammonium groups.
- the latices are generally used as aqueous dispersions. If the preparation is carried out in a non-aqueous medium, the solvent is removed by known methods, such as. B. by distillation, dialysis, ultrafiltration or by flaking and redispersing.
- the latices are generally mixed with natural or synthetic binders such as gelatin or other hydrophilic macromolecular substances.
- the amount of latex added is usually 20 to 85% by weight, preferably 50 to 85% by weight, based on the total amount of the binder used.
- the latices according to the invention are preferably used in a mixture with gelatin as a binder.
- the latices of the invention can advantageously be used in a wide variety of photographic materials, both in photosensitive and non-photosensitive layers of such materials.
- non-light-sensitive layers include receiving layers as used in diffusion transfer materials, further photographic auxiliary layers used in connection with light-sensitive layers.
- the latices can be used as a binder or for modifying the binder.
- Latex 1 As described under Latex 1, the starting latices A to D were reacted with various amines. The reaction conditions and the degree of conversion are given in Table 1 below.
- the latices 1 to 5 can be used as binder additives.
- a 10 wt .-% aqueous binder solution consisting of a mixture of gelatin and linear high molecular weight polyacrylamide in a weight ratio of 10: 1 and 100 ml of a 0.2 wt .-% solution of the below.
- Hardening agent A in water was poured onto a cellulose triacetate base provided with an adhesive layer using a conventional cascade casting machine and dried.
- the curing agent A used has the formula
- the material was stored for 7 days at 30 ° C and 50% relative humidity.
- the wet scratch resistance (NKF) and the swelling factor (QF) were then measured.
- a metal tip of a defined size is passed over the wet layer and loaded with increasing weight.
- the wet scratch resistance is indicated by the weight at which the tip leaves a visible scratch mark on the layer.
- a high weight corresponds to a high wet scratch resistance.
- the swelling is measured gravimetrically after treatment of a test strip in distilled water at 22 ° C. for 10 minutes. It is characterized by the swelling factor:
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Claims (3)
ia somme des pourcentages x, y et z devant être chaque fois de 100 % et les liants synthétiques répondant à la formule, ayant un reste qui remplit la fonction d'un coupleur chromogène, d'un absorbeur d'UV, d'un coupleur pour blanc, d'un colorant, d'un développateur, d'un composé éliminant ou libérant un colorant, d'un azurant optique, d'un générateur d'ions métalliques, d'un agent anti-voile, d'un toner, d'un composé réactif vis-à-vis du formaldéhyde ou d'un agent mordant, n'étant pas revendiqués.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3217020 | 1982-05-06 | ||
DE19823217020 DE3217020A1 (de) | 1982-05-06 | 1982-05-06 | Photographisches aufzeichnungsmaterial |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0093924A2 EP0093924A2 (fr) | 1983-11-16 |
EP0093924A3 EP0093924A3 (en) | 1985-01-09 |
EP0093924B1 true EP0093924B1 (fr) | 1987-05-27 |
Family
ID=6162923
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP83103982A Expired EP0093924B1 (fr) | 1982-05-06 | 1983-04-23 | Matériel d'enregistrement photographique |
Country Status (5)
Country | Link |
---|---|
US (1) | US4513080A (fr) |
EP (1) | EP0093924B1 (fr) |
JP (1) | JPS58214146A (fr) |
CA (1) | CA1248392A (fr) |
DE (2) | DE3217020A1 (fr) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0666029B2 (ja) * | 1984-03-09 | 1994-08-24 | 富士写真フイルム株式会社 | 写真感光材料 |
JPS6169061A (ja) * | 1984-09-12 | 1986-04-09 | Fuji Photo Film Co Ltd | ハロゲン化銀写真感光材料 |
EP0185793A1 (fr) * | 1984-12-24 | 1986-07-02 | Agfa-Gevaert N.V. | Latex d'un copolymère et matériaux photographiques à base d'halogénures d'argent contenant un tel latex |
EP0219101B1 (fr) * | 1985-10-16 | 1992-12-30 | Konica Corporation | Matériau photographique à l'halogénure d'argent |
EP0224951A1 (fr) * | 1985-11-26 | 1987-06-10 | Agfa-Gevaert N.V. | Elément récepteur d'image comprenant des agents anti-altération de couleurs |
JPS62178233A (ja) * | 1986-01-31 | 1987-08-05 | Konishiroku Photo Ind Co Ltd | ハロゲン化銀カラ−写真感光材料 |
DE3765765D1 (de) * | 1987-01-16 | 1990-11-29 | Agfa Gevaert Nv | Polymere als beizmittel fuer saure farbstoffe. |
JPS63257751A (ja) * | 1987-04-15 | 1988-10-25 | Fuji Photo Film Co Ltd | ハロゲン化銀カラ−写真感光材料 |
JPH07122747B2 (ja) * | 1987-09-11 | 1995-12-25 | 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 |
IT1232339B (it) * | 1989-09-25 | 1992-01-28 | Minnesota Mining & Mfg | Elementi fotografici multistrato aventi una migliorata qualita' di stesa. |
JPH0466934A (ja) * | 1990-07-04 | 1992-03-03 | Fuji Photo Film Co Ltd | ハロゲン化銀写真感光材料 |
GB9203350D0 (en) * | 1992-02-17 | 1992-04-01 | Ici Plc | Polymeric film |
US5384235A (en) * | 1992-07-01 | 1995-01-24 | Eastman Kodak Company | Photographic elements incorporating polymeric ultraviolet absorbers |
US5858633A (en) * | 1994-12-21 | 1999-01-12 | Eastman Kodak Company | Photographic elements containing 3-alkyl group substituted 2-hydroxyphenylbenzotriazole UV absorbing polymers |
US5766834A (en) * | 1996-05-17 | 1998-06-16 | Eastman Kodak Company | Photographic element containing ultraviolet absorbing polymer |
US6136496A (en) * | 1998-02-08 | 2000-10-24 | Agfa-Gevaert, N.V. | Imaging element for making an improved printing plate according to the silver salt diffusion transfer process |
DE69806019D1 (de) * | 1998-11-23 | 2002-07-18 | Agfa Gevaert Nv | Verfahren zur Herstellung eines Bildelements, das zur Herstellung einer Druckplatte nach dem Silbersalz-Diffusionsübertragungsverfahren verwendet werden kann |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1101409A (en) * | 1965-06-01 | 1968-01-31 | Fuji Photo Film Co Ltd | Improvements in and relating to photographic light sensitive materials |
US3615624A (en) * | 1968-01-29 | 1971-10-26 | Eastman Kodak Co | Peptizers for silver halide emulsions useful in photography |
US3591387A (en) * | 1969-04-02 | 1971-07-06 | Eastman Kodak Co | Silver halide emulsions comprising polymeric acrylamides as sensitizing additives |
US3852073A (en) * | 1970-12-31 | 1974-12-03 | Polaroid Corp | Silver halide emulsions comprising polymeric peptizers |
GB1381263A (en) * | 1971-01-11 | 1975-01-22 | Agfa Gevaert | Polymeric mordanting agents for anionic compounds |
US3816129A (en) * | 1973-01-02 | 1974-06-11 | Polaroid Corp | Synthetic silver halide emulsion binder |
DE2304319A1 (de) * | 1973-01-30 | 1974-08-08 | Agfa Gevaert Ag | Polymere verbindungen und ihre verwendung in photographischen farbmaterialien |
DE2541754C2 (de) * | 1975-09-19 | 1986-01-09 | Agfa-Gevaert Ag, 5090 Leverkusen | Photographische Silberhalogenidemulsion |
GB1581439A (en) * | 1976-06-15 | 1980-12-17 | Agfa Gevaert | Polymeric coupler latices for use in silver halide photography |
US4193800A (en) * | 1977-10-24 | 1980-03-18 | Konishiroku Photo Industry Co., Ltd. | Photographic dye mordant |
US4145221A (en) * | 1977-11-08 | 1979-03-20 | Gaf Corporation | Synthetic polymer latices in photographic silver halide emulsions containing multivalent metal salts |
JPS5931696B2 (ja) * | 1978-03-20 | 1984-08-03 | コニカ株式会社 | カラ−拡散転写法用写真材料 |
JPS5933899B2 (ja) * | 1978-08-31 | 1984-08-18 | 富士写真フイルム株式会社 | 写真感光材料 |
US4193796A (en) * | 1978-12-20 | 1980-03-18 | Eastman Kodak Company | Polymers for use in image receiving elements for metallizable dyes in image transfer film units |
EP0027284B1 (fr) * | 1979-10-15 | 1983-09-14 | Agfa-Gevaert N.V. | Latex à base de copolymères et matériaux photographiques aux halogénures d'argent contenant ce latex |
JPS6021370B2 (ja) * | 1979-11-05 | 1985-05-27 | 富士写真フイルム株式会社 | 写真感光材料 |
US4288523A (en) * | 1980-03-14 | 1981-09-08 | Polaroid Corporation | Diffusion control layers in diffusion transfer photographic products |
JPS6022340B2 (ja) * | 1980-04-07 | 1985-06-01 | 富士写真フイルム株式会社 | 写真感光材料 |
JPS5719735A (en) * | 1980-07-10 | 1982-02-02 | Fuji Photo Film Co Ltd | Photographic sensitive material |
JPS5794752A (en) * | 1980-12-05 | 1982-06-12 | Fuji Photo Film Co Ltd | Color photographic sensitive silver halide material |
-
1982
- 1982-05-06 DE DE19823217020 patent/DE3217020A1/de not_active Withdrawn
-
1983
- 1983-04-23 EP EP83103982A patent/EP0093924B1/fr not_active Expired
- 1983-04-23 DE DE8383103982T patent/DE3371819D1/de not_active Expired
- 1983-05-04 JP JP58077666A patent/JPS58214146A/ja active Pending
- 1983-05-04 CA CA000427420A patent/CA1248392A/fr not_active Expired
-
1984
- 1984-09-10 US US06/648,616 patent/US4513080A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
EP0093924A3 (en) | 1985-01-09 |
DE3217020A1 (de) | 1983-11-10 |
EP0093924A2 (fr) | 1983-11-16 |
JPS58214146A (ja) | 1983-12-13 |
US4513080A (en) | 1985-04-23 |
DE3371819D1 (en) | 1987-07-02 |
CA1248392A (fr) | 1989-01-10 |
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