US3189451A - Light sensitive reproduction material comprising a colloid containing an aldehyde and a diazotized phenyl amine compound and use thereof - Google Patents

Light sensitive reproduction material comprising a colloid containing an aldehyde and a diazotized phenyl amine compound and use thereof Download PDF

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US3189451A
US3189451A US179489A US17948962A US3189451A US 3189451 A US3189451 A US 3189451A US 179489 A US179489 A US 179489A US 17948962 A US17948962 A US 17948962A US 3189451 A US3189451 A US 3189451A
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aldehyde
weight
diazonium
light sensitive
parts
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Reichel Maximilian Karl
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Azoplate Corp
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Azoplate Corp
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/016—Diazonium salts or compounds
    • G03F7/0166—Diazonium salts or compounds characterised by the non-macromolecular additives
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/12—Production of screen printing forms or similar printing forms, e.g. stencils

Definitions

  • the present invention relates to a light sensitive reproduction material comprising a support and a colloid layer which contains, as the sensitizing agent which effects tanning of the colloid under the influence of light, a mixture of a diazo compound and an aldehyde.
  • a light sensitive material which comprises a support and a colloid layer containing a diazo compound as a sensitizing substance, and in which the colloid layer contains at least one aldehyde and one or more diazo compounds of amines, corresponding to the following general formula HzN- NH-Br in which R, is an alkyl, aryl, aralkyl, cycloalkyl or a heterocyclic residue R is hydrogen, halogen, alkyl,
  • n is an integer from 1 to 2;
  • Amines which may be used, in accordance with the general formula above, are, e.g.: p-aminodiphenylamine, 4- amino-4'-methyl diphenylarnine, 4-amino-3'-methyl-diphenylarnine, 4-amino-4-methoxy-diphenylam-ine, 4-arnino 4 chloro-diphenylamine, 4-amino-4-nitrodiphenylamine, 1-monoethylamino-Z-methylt-aminobenzene, monoethylamino-3-carboxy-4*aminobenzene, tylamino-3-chloro-4 amino-benzene, l-rnonocyclohexylamine-3-methyl-4-arninobenzene, 1-mono-2,6-dichlorobenzylamino-4-aminobenzene, and l-mono-6-ethoxy-benzthiazolylamino-4-arnino-benzene.
  • the amines are applied in the form of their diazotizaalkoxy, or a nitro or carl-monobution products.
  • the diazonium chlorides, diazonium bromides, diazonium sulfates, diazonium borofiuorides and the double salts, in particular the zinc chloride double salts of the halides, are exemplary. Mixtures of such diazonium salts may also be used.
  • aldehydes examples include: lower aliphatic aldehydes, such as formaldehyde, acetaldehyde, propionaldehyde, chloroacetaldehyde,
  • trichloroacetaldehyde, glyoxal, glutardialdehyde, butyrviolet light are of particular advantage.
  • aldehyde also aromatic aldehydes, such as cinnamaldehyde, resorcylaldehyde, salicylaldehyde, stilbenealdehyde, and terephthaldialdehyde; and heterocyclic aldehydes, such as furfural, and pyridine-4-aldehyde. Mixtures of aldehydes may also be applied.
  • Suitable colloids for the light sensitive material of the present invention are, e.g.: gelatin, polyvinyl pyrrolidone, polyacrylic acid, egg albumin, casein, photographic paste and cellulose ethers; particularly suitable is polyvinyl alcohol, in admixture with polyvinyl acetate, if desired, to which plasticizers, such as dibutyl phthalate tricresyl phosphate, dioctyl phthalate, or benzylbutyl phthalate are advantageously added.
  • the base is a saponifiable plastic foil, such as a cellulose acetate foil
  • the surface layer which forms upon saponification e.g. the layer ofhydrate of cellulose which forms, may serve as the colloid.
  • Base materials which may be used as supports for the colloid layers according to the present invention are pretreated papers generally used for printing plates, plastic foils, metal supports, e.g. of aluminum, zinc, or copper, or highly porous materials, in particular fabrics or fibrous fleeces, consisting of materials such as polyamides, polyesters, polyacrylonitrile, polyvinylidene chloride, and cottori, or of metal, e.g. bronze, brass or copper.
  • the supports are coated with the colloid solution containing the diazo compound and the aldehyde.
  • the solution is either applied by casting, whirling or spraying, or the material is passed through the solution, or the solution may be applied by means of rollers or brushes or by any other suitable method, and subsequently dried.
  • the reproduction material ac cording to the present invention may be used in known manner for the preparation of planographic printing plates.
  • the material is exposed under a master, whereby the light-struck areas of the colloid layers are hardened.
  • the colloid layer in the areas which were not struck by light, is removed by a suitable solvent, in most cases water, and the tanned image thus produced is inked up with greasy ink and used for the production of prints.
  • the material according to the present invention may be advantageously used for the production of screen printing stencils.
  • the diazonium compounds are added to the colloid solutions in amounts ranging from about 0.1 to 6 percent by weight, preferably 0.5 to 2.5 percent; the aldehydes are added to the colloid solutions in quantities such that the molar ratio of aldehyde to diazonium compound in the range of from 1:1 to 20:1, preferably 5:1 to 10:1.
  • the colloid solutions may contain fillers in finely distributed form. This may frequently be of advantage when the colloid solutions are to be used for screen printing.
  • the fillers are applied in a finely divided and uniforrnly distributed form, i.e. in grain sizes of from S to 30 preferably 10 to 20 Suitable fillers are e.g. polyvinyl alcohol, polyamide, titanium' dioxide, silicon diioxide, or starch.
  • The, light sensitive solutions may also be colored, in which case dyestuffs which have low absorption of ultra Such dyestuffs are, e.g. Methylviolet BB (Schultz Farbstofftabellen, 7th edition, volume 1 (1931), page 327, No. 763), Rosaniline hydrochloride (Schultz Farbstoiftabellen, page 326, No.
  • the light sensitive material according to the preserit invention shows excellent tanning characteristics under the action of light. This was unexpected, since, in genera the single components, eg p-diazodiphenylamine or formaldehyde, have practically no tanning effect on colloids under the influence of light, even under conditions which favor tanning, e.g. at a relative humidity, at 40 C., of 60%. On the other hand, the addition of aldehyde will cause an improvement of the tanning action where the organic diazo compounds used have a tanning effect by themselves. Moreover, by means of this combination of diazo compounds and aldehydes, solutions may be prepared the shelf-life of which is by far superior to that of solutions prepared, e.g., with a high molecular weight condensation product. Further, it is not necessary to prepare such condensation products.
  • Example I A superficially saponified cellulose acetate foil is immersed in a solution consisting of 1 part by weight of the diazonium chloride of p-amino-diphenylamine and 2 parts by weight of a 40 percent formaldehyde solution in 100 parts by volume of water, and excess solution is removed by squeeze rollers. After drying by means of hot air, the foil is exposed under a photographic negative and then rinsed with running water. After the usual fixing of the foil with an aqueous solution of gum arabic, methyl cellulose, or dextrin, to which some phosphoric acid has been added, the foil may be used for printing on a planographic or offset machine. Positive prints are obtained.
  • a paper foil provided with a hydrophilic surface, e.g. a cellulose methyl ether surface.
  • the same amounts may be used of the diazonium bromide, the diazonium sulfate or the borofluoride of the p-amino-diphenylamine, the results being equivalent.
  • Example 11 One part by weight of the diazonium sulfate of 4-aminodiphenylamine is dissolved in 100 parts by weight of a percent solution of polyvinyl alcohol (e.g. Mowiol No. -88) and to this solution 2 parts by weight of a percent formaldehyde solution are added, with stirring, at room temperature. A polished copper plate is coated with this solution on a plate whirler. After exposure under a diapositive, the parts of the layer not. struck by light are removed with running water, and, after drying with hot air, the bared copper surface is etched with an iron-3-chloride solution having a gravity of 40 B. A printing plate suitable for intaglio printing is thus obtained.
  • a percent solution of polyvinyl alcohol e.g. Mowiol No. -88
  • polyvinyl alcohol a dispersion of polyvinyl acetate in dibutyl phthalate may be used.
  • Example III The procedure described in Example 11 is followed, using, instead of the support mentioned in Example II, a copper foil of 30 to 70p thickness laminatedto a dielectric plastic foil. After exposure, under a photographic negative of a wiring system, the areas not struck by light during exposure are removed by means of running water, the
  • Example IV One part by weight of the diazonium chloride of p-aminodiphenylamine and 2 parts by weight of a 40 percent formaldehyde solution are introduced, with stirring, into parts by volume of an aqueous emulsion consisting of polyvinyl alcohol, polyvinyl acetate, and dibutyl phthalate.
  • the now light-sensitive emulsion is poured into a grooved scraper, which may be made of metal or plastic material, andapplied to a fabric drawn tautly over a frame and consisting of e.g. a polyamide, such as polye-amino-caprolactam, nylon, metal gauze, glass fiber, polyester, or natural silk.
  • a polyamide such as polye-amino-caprolactam
  • a screen printing stencil is thus obtained which is thoroughly hardened and has excellent sharpness of edges of the stencil, as well as of the prints produced therefrom.
  • diazonium chloride of p-amino-diphenylamine instead of 1 part by weight of the diazonium chloride of p-amino-diphenylamine there may be used, e.g., a mixture of 0.5 part by weight of the diazonium chloride and 0.5 part by weight of the diazonium sulfate of p-aminodiphenylamine.
  • the emulsion used in this example is prepared as follows: 100 part by weight of polyvinyl alcohol (Mowiol No. 30-88) in 580 parts by volume of distilled water are heated on a steam bath for 6 to 8 hours, with mechanical stirring. After the mixture has cooled to room temperature, 100 parts by weight of dibutyl phthalate are added, with mechanical stirring, and, after 15 minutes, a dispersion of 600 parts by weight of pulverized polyvinyl acetate (Vinnapas D-SO or Vinnapas H-60) in 900 parts by volume of distilled water is introduced.
  • Example V The method described in Example IV is followed, but instead of the emulsion of polyvinyl alcohol, polyvinyl acetate, and dibutyl phthalate, there is used an emulsion consisting of polyvinyl acetate and dibutyl phthalate only.
  • An excellent stencil for screen printing is thus obtained which has very sharp edges of the stencil as well as of the prints produced therefrom.
  • Example VI The method described in Example IV is followed using, instead of 1 part by weight of the diazonium chloride of p-aminodiphenylamine and 2 parts by weight of formaldehyde (corresponding to 5 parts by volume of a 40 per cent formalin solution), 1.3 parts by weight of the condensation product of 4-diazonium phenlyamine and formaldehyde, in the form of the zinc chloride double salt, and 2 parts by weight of formaldehyde (corresponding to 5 parts by volume of a 40 percent formalin solution).
  • a screen printing stencil is thus obtained which shows an outstanding degree of hardening, while a screen printing stencil prepared with the same amount of the Zinc chloride complex, but without the addition of 5 parts by volume of 40 percent formalin solution, is insufliciently tanned.
  • Example VII The method described in Example IV is followed using, however, instead of the emulsion of polyvinyl alcohol, polyvinyl acetate, and dibutyl phthalate, an emulsion in which the polyvinyl alcohol was replaced by an 8 to 10 percent aqueous solution of an epoxy resin (Polyox, watersoluble resin of Union Carbide International Company, New York city, N.Y., U.S.A.) A stencil is thus obtained which is very suitable for screen printing and which excels in sharpness of edge of the stencil as well as of the prints produced therewith.
  • an epoxy resin Polyox, watersoluble resin of Union Carbide International Company, New York city, N.Y., U.S.A.
  • the same amount of the diazo borofiuoride of p-aminodiphenylamine may be used with good results.
  • Example VIII The method described in Example IV is followed, using, instead of the emulsion of polyvinyl alcohol, polyvinyl acetate, and dibutyl phthalate, an emulsion in which polyvinyl alcohol was replaced by a percent solution of the sodium salt of carboxymethylcellulose. An excellent screen printing stencil is thus obtained which has very sharp edges of the stencil as well as the prints produced therewith.
  • the same amount of the diazonium sulfate of p-aminodiphenylamine may be used with good results.
  • Example IX The method described in Example IV is followed, but instead of 2 parts by weight of formaldehyde, 2 parts by weight of furfural are used. A screen printing stencil is obtained which is excellently hardened and has extremely sharp contours of the stencil as well asof the prints produced therewith.
  • acetaldehyde instead of 2 parts by weight of furfural, the same amounts by weight of acetaldehyde, chloroacetaldehyde, glyoxal, glutardialdehyde, butyror isobutyraldehyde, propionaldehyde, isovaleraldehyde, or crotonaldehyde may be used, with equally good results.
  • Example X The method described in Example IV is followed, using, instead of 2 parts by weight of formaldehyde, 2 parts by weight of cinnamaldehyde. A screen printing stencil is thus obtained which is well hardened and in which the stencil as well as the prints made from it have excellently sharp edges.
  • cinnamaldehyde instead of 2 parts by weight of cinnamaldehyde, there may be used, with good results, the same amounts of pyridine-4-aldehyde, resorcylaldehyde, salicylaldeyhde, stilbenealdehyde, or terephthalaldehyde.
  • Example XI Example XII The method described in Example 1V is followed using, however, 1 part by weight of the diazonium chloride of lmonoethylamino-2-methyl-4-aminobenzene instead of 1 part by weight of the diazonium chloride of 4-aminp-diphenylamine. A very thoroughly hardened screen printing stencil is thus obtained.
  • diazonium chloride of 1-monoethyl-amino-2-methyl-4-aminobenzene there may be used 1 part by weight of either of the diazonium chlorides of 1-monoethylamine-3-carboxy-4-aminobenzene, l-monobutyl-amino-3-chloro-4-arn-inobenzene, or 1- monocyclohexylamino-3-methyl-4-aminobenzene.
  • Example XIII The method described in Example IVis followed, using, instead of 1 part by weight of the diazonium chloride of 4-arnino-diphenylamine, 1 part by weight of the diazonium chloride of l-mono-6-othoxybeuz thiazolylamino-4-bcnzene. A screen printing stencil is obtained which is thoroughly hardened.
  • Exalnple XIV 1 part by weight of the diazonium chloride of p-aminodiphenylamine and 5 parts by volume of a percent formaldehyde solution are added, with mechanical stirring, to 100 parts by volume of a 2 percent solution of hydroxyethyl cellulose in which 10 parts by weight of pulverized polyvinyl acetate were dispersed.
  • the light sensitive emulsion thus obtained is poured into a grooved scraper of metal or plastic material and then applied to a fabric, e.g. a commercially available superpolyamide fabric or metal gauze, tautly drawn over a tentering frame. Subsequently, the coated fabric is dried at a temperature above 40 C.
  • a screen printing stencil is thus obtained which is thoroughly hardened and possesses very sharp edges, so that the prints obtained therefrom have very good contours.
  • Example XV The method described in Example IV is followed, using, however, instead of the aqueous emulsion of polyvinyl alcohol, polyvinyl acetate, and dibutyl phthalate, an emulsion containing 15 parts by weight of polyvinyl alcohol (Mowiol 5098), dissolved in parts by volume of water, and 7.5 parts by weight of dispersed polyvinyl alcohol (Mowiol 1/2 50-98).
  • a screen printing stencil is thus obtained which is thoroughly hardened and has excellently sharp contours of the stencil as well as of the copies produced with the stencil.
  • Light sensitive material comprising a carrier and a colloid layer, the latter including at least one aldehyde and at least one diazo compound of an amine having the formula H N- N-Ri i the colloid layer includes a dyestuff.
  • aldehyde is selected from the group consisting of trichloroacctaldehyde, cinnarnaldehyde, pyridine-t-aldehyde,
  • the diazo compound is selected from the group consisting of the diazonium chlorides of l-monoethylamine 3 carboxy-4-aminobenzene, l-monobutylamino-3- chloro-4-aminobenzene and 1-monocyclohexyl-arnino-3- methyl-4-aminobenzene.
  • a process for developing light sensitive material comprising exposing a supported colloid layer to a light image and removing from the support those portions of the colloid layer which were not struck by light by treatment with a solvent, the colloid layer including at least one aldehyde and at least one diazo compound of an amine having the formula in which R is selected from the group consisting of alkyl, aryl, aralkyl, cycloalkyl and heterocyclic groups, R is selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, nitro, and carboxyl groups, and n is an integer from 1 to 2.
  • aldehyde is a lower aliphatic aldehyde.
  • a process according to claim 15 in aldehyde is an aromatic aldehyde.
  • a process according to claim 15 in aldehyde is a heterocyclic aldehyde.
  • a process according to claim 15 in aldehyde is formaldehyde.
  • aldehyde is selected from the group consisting of trichloroacetaldehyde, cinnamaldehyde, pyridine-4-aldehyde, resorcylaldehyde, salicylaldehyde, stilhenealdehyd: and terephthalaldehyde.
  • a process according to claim 15 in which the diazo compound is the diazonium chloride of p-arninodiphenylamine.
  • a process according to claim 15 in which the diazo compound is selected from the group consisting of the diazonium chlorides of 1-monoethylamine-3-carboxy- 4-aminobenzene, l-monobutylamino 3-chloro 4-aminobenzene and l-monocyclohexyl-amino-3-rnethyl-4-amino benzene.
  • Light sensitive material comprising a carrier and a colloid layer, the latter including formaldehyde and a condensation product of an aldehyde and a diazo compound of an amine having the formula in which R is selected from the group consisting of alkyl, aryl, aralkyl, cycloalkyl and heterocyclic groups, R is selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, nitro, and carboxyl groups, and n is an integer from 1 to 2.
  • a process for developing light sensitive material comprising exposing a supported colloid layer to a light image and removing from the support those portions of the colloid layer which were not struck by light by treatment with a solvent, the colloid layer including formaldehyde and a condensation product of an aldehyde and a diazo compound of an amine having the formula in which R is selected from the group consisting of alkyl, aryl, aralkyl, cycloalkyl and heterocyclic groups, R is selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, nitro, and carboxyl groups, and n is an integer from 1 to 2.
  • condensation product is of 4-diazonium phenylarnine and formaldehyde, in the form of the zinc chloride double salt.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
US179489A 1961-03-15 1962-03-13 Light sensitive reproduction material comprising a colloid containing an aldehyde and a diazotized phenyl amine compound and use thereof Expired - Lifetime US3189451A (en)

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DEK43194A DE1206308B (de) 1961-03-15 1961-03-15 Lichtempfindliche Schicht mit gerbenden Eigenschaften
DEK0050933 1963-09-26

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US399106A Expired - Lifetime US3322541A (en) 1961-03-15 1964-09-24 Light sensitive coatings with tanning properties

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BE (2) BE653467A (en(2012))
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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3294541A (en) * 1963-09-25 1966-12-27 Keuffel & Esser Co Diazo-light-sensitive copying material
US3322541A (en) * 1961-03-15 1967-05-30 Azoplate Corp Light sensitive coatings with tanning properties
US3390992A (en) * 1964-06-15 1968-07-02 North American Rockwell Non-etching circuit fabrication
US3853561A (en) * 1970-11-26 1974-12-10 Hoechst Ag Process for the preparation of screen printing stencils using intermediate support for light sensitive layer
US4154614A (en) * 1975-07-02 1979-05-15 Nippon Paint Co., Ltd. Photosensitive diazo composition with graft copolymer for use in printing screen
US4492748A (en) * 1981-09-10 1985-01-08 Walter Lutz Light-sensitive polycondensation product containing diazonium and dialdehyde groups, and light-sensitive recording material prepared therewith
US4564581A (en) * 1981-06-19 1986-01-14 Sericol Group Limited Process of preparing screen stencil using diazo photosensitive compositions with acidic p-H indicator
US5134057A (en) * 1988-10-10 1992-07-28 501 Ppg Biomedical Systems, Inc. Method of providing a substrate with a layer comprising a polyvinyl based hydrogel and a biochemically active material

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3463638A (en) * 1965-08-20 1969-08-26 Ibm Heat-fixable light-sensitive compositions and elements
DE2057473C2 (de) * 1970-11-23 1982-04-08 Hoechst Ag, 6000 Frankfurt Lichtempfindliches Gemisch
DE2058178C2 (de) * 1970-11-26 1982-04-01 Hoechst Ag, 6000 Frankfurt Verfahren zur Herstellung von Siebdruckformen
DE2522225C2 (de) * 1975-05-20 1983-12-08 Nippon Paint Co., Ltd., Osaka Wässriges lichtempfindliches Gemisch und seine Verwendung für die Herstellung von Siebdruckschablonen
FR2411432A1 (fr) * 1977-12-09 1979-07-06 Issec Labo Physicochimie Appli Procede d'impressions couleur photochimique et dispositif pour sa mise en oeuvre
FR2866887A1 (fr) * 2004-02-27 2005-09-02 Oreal Para-phenylenediamine secondaire n-heteroaryle, compositon tinctoriale comprenant une telle para-phenylenediamine, procede mettant en oeuvre cette composition et utilisation
US7329288B2 (en) 2004-02-27 2008-02-12 L'oreal S.A. N-heteroaryl secondary para-phenylenediamine, a dye composition comprising such a para-phenylenediamine, a process for preparing this composition and use thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2063631A (en) * 1932-05-23 1936-12-08 Kalle & Co Ag Diazo compounds and a process of preparing them
US2679498A (en) * 1954-05-25 Atent office
US3012886A (en) * 1954-05-10 1961-12-12 Harry H Lerner Emulsion coating and method of preparation
US3029146A (en) * 1955-02-25 1962-04-10 Azoplate Corp Reproduction material

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL70798C (en(2012)) * 1948-10-15
NL150528B (nl) * 1949-05-14 Hollandse Signaalapparaten Bv Werkwijze voor het vervaardigen van twistloos of nagenoeg twistloos garen en het door toepassing van deze werkwijze verkregen garen.
US2690968A (en) * 1952-10-04 1954-10-05 Powers Chemco Inc Development of diazo and azide sensitized colloids
BE528898A (en(2012)) * 1953-05-28
US2937085A (en) * 1954-01-11 1960-05-17 Ditto Inc Composite photosensitive plate, and method of making printing plate therefrom
BE549814A (en(2012)) * 1955-07-29
AT209359B (de) * 1958-01-22 1960-06-10 Kalle & Co Ag Lichtempfindliches Reproduktionsmaterial, bestehend aus Schichtträger und lichtempfindlicher Kolloidschicht
US3130051A (en) * 1958-12-10 1964-04-21 Gen Aniline & Film Corp Process for producing negative working offset diazo printing plates
US2976152A (en) * 1958-12-19 1961-03-21 Gen Aniline & Film Corp Photographic gelatin layers containing triazine hardeners
BE595534A (en(2012)) * 1959-10-02
NL275561A (en(2012)) * 1961-03-15

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2679498A (en) * 1954-05-25 Atent office
US2063631A (en) * 1932-05-23 1936-12-08 Kalle & Co Ag Diazo compounds and a process of preparing them
US3012886A (en) * 1954-05-10 1961-12-12 Harry H Lerner Emulsion coating and method of preparation
US3029146A (en) * 1955-02-25 1962-04-10 Azoplate Corp Reproduction material

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3322541A (en) * 1961-03-15 1967-05-30 Azoplate Corp Light sensitive coatings with tanning properties
US3294541A (en) * 1963-09-25 1966-12-27 Keuffel & Esser Co Diazo-light-sensitive copying material
US3390992A (en) * 1964-06-15 1968-07-02 North American Rockwell Non-etching circuit fabrication
US3853561A (en) * 1970-11-26 1974-12-10 Hoechst Ag Process for the preparation of screen printing stencils using intermediate support for light sensitive layer
US4154614A (en) * 1975-07-02 1979-05-15 Nippon Paint Co., Ltd. Photosensitive diazo composition with graft copolymer for use in printing screen
US4564581A (en) * 1981-06-19 1986-01-14 Sericol Group Limited Process of preparing screen stencil using diazo photosensitive compositions with acidic p-H indicator
US4492748A (en) * 1981-09-10 1985-01-08 Walter Lutz Light-sensitive polycondensation product containing diazonium and dialdehyde groups, and light-sensitive recording material prepared therewith
US5134057A (en) * 1988-10-10 1992-07-28 501 Ppg Biomedical Systems, Inc. Method of providing a substrate with a layer comprising a polyvinyl based hydrogel and a biochemically active material

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DE1206308B (de) 1965-12-02
BE653467A (en(2012)) 1965-03-23
SE317257B (en(2012)) 1969-11-10
NL6410778A (en(2012)) 1965-03-29
GB998838A (en) 1965-07-21
US3322541A (en) 1967-05-30
CH459760A (de) 1968-07-15
CH419833A (de) 1966-08-31
DE1447729B (de) 1969-09-04
GB1069366A (en) 1967-05-17
NL275561A (en(2012))
SE334813B (en(2012)) 1971-05-03
BE615056A (en(2012))

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