US3061429A - Diazo printing plates and method for the production thereof - Google Patents

Diazo printing plates and method for the production thereof Download PDF

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Publication number
US3061429A
US3061429A US709185A US70918558A US3061429A US 3061429 A US3061429 A US 3061429A US 709185 A US709185 A US 709185A US 70918558 A US70918558 A US 70918558A US 3061429 A US3061429 A US 3061429A
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Prior art keywords
diphenylamine
diazonium
printing plate
polyacrylic acid
layer
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US709185A
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English (en)
Inventor
Neugebauer Wilhelm
Rebenstock August
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Azoplate Corp
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Azoplate Corp
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Classifications

    • 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
    • G03F7/021—Macromolecular diazonium compounds; Macromolecular additives, e.g. binders
    • G03F7/0212—Macromolecular diazonium compounds; Macromolecular additives, e.g. binders characterised by the polymeric binder or the macromolecular additives other than the diazo resins or the polymeric diazonium compounds

Definitions

  • This invention relates to a novel presensitized printing plate containing a diazo compound, and to a method for the production thereof, and, more particularly, to a novel presensitized printing plate which can be developed merely by washing with water, thereby eliminating the alkali or acid treatment required with printing plates known to the prior art.
  • Diazo compounds of higher molecular weight such as condensation products of aldehydes with diazo compounds, for example the diazo compounds of p-amino-diphenylamine, have been proposed for the tanning of colloid layers, and best results are obtained when these diazo compounds constitute about percent by weight of the dry colloid applied to the base material, such as aluminum, for example.
  • the foregoing plates consisting of base materials coated with layers consisting of water-soluble colloids sensitized by means of diazo compounds have not found practical application in the printing trade.
  • the light-hardened colloid particles of these layers are not capable of holding the greasy ink in flat and offset printing, and the mechanical strength of the hardened colloids is insuflicient to permit long runs.
  • the present invention it has been found that excellent flat and offset printing plates can be produced from light-sensitive material consisting of a support having a colloid layer thereon, the colloid layer comprising a polyacrylic acid and containing a diazonium chloride or bromide of a p-amino-diphenylamine as the light-sensitive substance.
  • the percentage of the diazo compounds to be employed according to the present invention is from about 75 to 400 percent by weight, preferably between about 100 to 200 percent by weight of the dry weight of the polyacrylic acid.
  • Both com- .ponents may be applied in either an aqueous solution or dissolved in a suitable organic solvent, such as ethylene glycol monomethyl ether, or they also may be applied in mixtures of organic solvents with water.
  • a suitable organic solvent such as ethylene glycol monomethyl ether
  • the percentage of a polyacrylic acid in the coating solution may vary widely, and preferably it is about 1 to 2 percent by weight. If granulated zinc plates are used, best results are obtained by using a concentration of about 2 to 3 percent by weight.
  • the solutions of polyacrylic acid and the diphenylaminep-diazonium chloride or bromide are coated on the base material according to known procedures, and the base material may be metal, such as aluminum or zinc, or may be a specially. treated paper foil, the treatment of the latter being a conventional treatment for such foil.
  • the coated support is then dried, preferably at an elevated temperature, such as about 90 C., for example.
  • the diazo chlorides or bromides of p-diazo-diphenyl- 3,051,429 Fatented Oct. 30, 1962 amine which may be used in the present invention, may be either substituted or unsubstituted, and the substituents in the aryl nuclei of the diphenylamine radical may be, for example, alkyl, alkoxy, halogen, hydroxy or sulfarylido radicals.
  • a diazonium salt radical in addition to the diazonium chloride or bromide radical, may be a substituent.
  • the molecule may contain one or more of these substituents, and compounds containing different substituents may also be employed.
  • substituted diazonium chlorides of p diazo-diphenylamines which may be used, are the following:
  • the colloid in the light-sensitive layer of the printing plates of this invention may be polyacrylic acid or polymethacrylic acid per se, or an acrylic-methacrylic acid copolymerizate, or the like.
  • the unexposed coated foils prepared in accordance with this invention have an excellent shelf life, and after exposing the light-sensitive foil in the usual manner under a negative original or master, development can be eifected by simply rinsing, swabbing or bathing the exposed foil with water. This can be accomplished, for example, by mounting the exposed foil on a printing machine and wiping it over with a sponge soaked in water. After this development, the first plates may be run off immediately, and no additional treatment with one of the so-called fixing agents, which is often required in ofiset printing, is necessary. Even without such aftertreatment, prints are obtained which are free of scum and the printing plates produced in accordance with this invention give very long runs.
  • the 4.-nitro-diphenylamines are prepared by reacting chloro-4-nitro-benzenesulfonic acids-(3) with aromatic amines, and then splitting off the sulfo group of the 4-nitro-diphenylamine sulfonic acids thus formed, by heating the sulfonic acids with sulfuric acid.
  • the 4-nitro-diphenylamine-Z-sulfanilide thus formed is dissolved in dioxane, and then catalytically reduced to the corresponding 4-amino-diphenylamine-2- sulfanilide.
  • This compound in the form of its hydrochloride, is then dissolved in dimethylformamide and slowly diazotized with a sodium nitrite solution in the presence of hydrochloric acid.
  • the compound 2-anilidosulfonyl-diphenylamine-4-diazonium chloride precipitates, which, after purification with ether, melts at a temperature of 178 to 180 C.
  • polyacrylic acid of the viscosity described there may be polyacrylic acids of higher or lower viscosities.
  • the foils may be pretreated with dilute solutions of caustic alkalies and nitric acids, or with solutions of tertiary alkali metal phosphates.
  • 3 parts by Weight of the diazonium chloride of p-amino-diphenylamine dissolved in 100 parts by weight of ethylene glycol monomethyl ether.
  • the coated plate was then dried, and after exposing the dried layer under a negative original, it was developed by rinsing with Water. The plate was then ready for use on a
  • EXAMPLE V Following the general procedure of Example III above, a paper printing foil was coated with the solution described in Example III, dried and then developed in accordance with the procedure of Example III. In this case also, printing could be begun immediately without the application of a special fixing agent, and long runs were obtained.
  • a fixing agent such as gum arabic or phosphoric acid
  • the polyacrylic acid may also be replaced by the same quantity of polymethacrylic acid or a 1:1 copolymerizate of acrylic acid and methacrylic acid.
  • the support for the light-sensitive layer may be an aluminum foil, previously treated at a temperature of about 20 C., first for 5 minutes with a 5 percent by weight caustic soda solution, and then for another 5 minutes with a 5 percent nitric acid solution, and then finally rinsed with water and dried.
  • a printing plate was prepared having a quality equivalent to that described in Example VI.
  • ethylene glycol monomethyl ether solution there may also be used an aqueous solution of polyacrylic acid and 4'-bromo-diphenylarnine-4- a diazonium chloride.
  • a paper printing foil may also be substituted for the aluminum foil and high quality plates are obtained.
  • the coating solution may contain the same quantity of 4'-methoxy-diphenylamine-4-diazonium bromide.
  • a polyacrylic acid as used in the following claims is intended to include likewise a polymethacrylic acid as well as copolymerizates of acrylic and methacrylic acid.
  • a presensitized printing plate comprising a hydrophilic base material having directly coated thereon a layer comprising a polyacrylic acid and a compound selected from the group consisting of the diazonium chloride and bromide of a p-amino-diphenylamine.
  • a presensitized printing plate comprising a hydrophilic base material having directly coated thereon a layer comprising a polyacrylic acid and a compound having the formula QKOWTX in which X is selected from the group consisting of chloro and bromo radicals.
  • a presensitized printing plate comprising a hydrophilic base material having directly coated thereon a layer comprising a polyacrylic acid and a compound hav ing the formula 8 Or-NH- I I in which X is selected from the group consisting of chloro and bromo radicals.
  • a presensitized printing plate comprising a hydrophilic base material having directly coated thereon a layer comprising a polyacrylic acid and a compound. havin which X is selected from the group consisting of chloro and bromo radicals.
  • a presensitized printing plate comprising a hydrophilic base material having directly coated thereon a layer comprising a polyacrylic acid and a compound having the formula in which X is selected from the group consisting of chloro and bromo radicals and X is an alkoxy radical.
  • a presensitized printing plate comprising a hydrophilic base material having directly coated thereon a layer comprising a polyacrylic acid and a compound having the formula Xi r r r in which X is selected from the group consisting of chloro and bromo radicals, and X and X are selected from the group consisting of hydrogen and alkoxy radicals.
  • a presensitized printing plate comprising a hydrophilic base material having directly coated thereon a layer comprising a polyacrylic acid and a compound having the formula in which X is'selected from the group consisting of chloro and bromo radicals, X is selected from the group consisting of hydrogen, fluoro, chloro, bromo, hydroxy, alkyl, and alkoxy radicals, and X is selected from the group consisting of hydrogen, sulfonamide, and alkoxy radicals.
  • a process for developing a printing plate which comprises exposing to light under a master a presensitized printing plate comprising a hydrophilic base material directly coated with a layer comprising a polyacrylic acid and a compound selected from the group consisting of the diazonium chloride and bromide of a p-amino-diphenylamine, and washing the exposed plate with Water.
  • a process for developing a printing plate which 8 comprises exposing to light under a master a presensitized printing plate comprising a hydrophilic base material directly coated with a layer comprising a polyacrylic acid and a compound having the formula in which X is selected from the group consisting of chloro andbromo radicals, and washing the exposed plate with Water.
  • a process for developing a printing plate which comprises exposing to light under a master a presensitized printing plate comprising a hydrophilic base material directly coated with a layer comprising a polyacrylic acid and a compound having the formula in which X is selected from the group consisting of chloro and bromo radicals, and washing the exposed plate with water.
  • a process for developing a printing plate which comprises exposing to light under a master a presensitized printing plate comprising a hydrophilic base material directly coated with a layer comprising a polyacrylic acid and a compound having the formula in which X is selected from the group consisting of chloro and bromo radicals, and washing the exposed plate with water.
  • a process for developing a printing plate which comprises exposing to light under a master a presensitized printing plate comprising a hydrophilic base material directly coated with a layer comprising a polyacrylic acid and a compound having the formula in which X is selected from the group consisting of chloro and bromo radicals and X is selected from the group consisting of fluoro, chloro, bromo, alkyl, hydroxy and alkoxy radicals, and washing the exposed plate with water.
  • a process for developing a printing plate which comprises exposing to light under a master a presensitized printing plate comprising a hydrophilic base material directly coated with a layer comprising a polyacrylic acid and a compound having the formula in which X is selected from the group consisting of chloro and bromo radicals and X is an alkoxy radical, and washing the exposed plate with water.
  • a process for developing a printing plate which comprises exposing to light under a master a presensitized printing plate comprising a hydrophilic base material directly coated with a layer comprising a polyacrylic acid and a compound having the formula X1 IO H in which X is selected from the group consisting of chloro and bromo radicals, and X and X are selected from the group consisting of hydrogen and alkoxy radicals, and washing the exposed plate with water.
  • a process for developing a printing plate which comprises exposing to light under a master a presensitized printing plate comprising a hydrophilic base material directly coated with a layer comprising a polyacrylic acid and a compound having the formula in which X is selected from the group consisting of chloro and bromo radicals, X is halogen, and X is an alkoxy radical, and washing the exposed plate with water.
  • a process for developing a printing plate which comprises exposing to light under a master a pre-sensitized printing plate comprising a hydnophilic base material directly coated with a layer comprising a polyacrylic acid and a compound having the formula in which X is selected from the group consisting of chloro and bromo radicals, X is selected from the group consisting of hydrogen, fluoro, chloro, lbromc, hydroxy, alkyl, and alkoxy radicals, and X is selected from the group consisting of hydrogen, sulfonamide, and alkoxy radicals, and washing the exposed plate with water.
  • a presensitized printing plate comprising a hydrophilic base material having directly coated thereon a layer comprising a polyacrylic acid and diphenylamine-4- diazonium chloride.
  • a presensitized printing plate comprising a hydrophilic base material having directly coated thereon a layer comprising a polyacrylic acid and diphenylamine-4- diazonium bromide.
  • a presensitized printing plate comprising a hydrophilic base material having directly coated thereon a layer comprising a polyacrylic acid and 4-bromo-diphenylamine-4-diazonium chloride.
  • a presensitized printing plate comprising a hydrophilic base material having directly coated thereon a layer comprising a polyacrylic acid and 4-chloro-diphenylamine-4-diazonium chloride.
  • a presensitized printing plate comprising a hydrophilic base material having directly coated thereon a layer comprising a polyacrylic acid and 2-anilido-sulfony1- diphenylamine-4-diazonium chloride.
  • a presensitized printing plate comprising a hydrophilic base material having directly coated thereon a layer comprising a polyacrylic acid and 2-(p-toluene-sulfonyl-amino)-diphenylamine-4-diazonium chloride.
  • a presensitized printing plate comprising a hydrophilic base material having directly coated thereon a layer comprising a polyacrylic acid and 4-bromo-diphenylamine-4-diazonium bromide.
  • a presensitized printing plate comprising a hydrophilic base material having directly coated thereon a layer comprising a polyacrylic acid and 4'-ch1oro-diphenylamine-4-diazonium bromide.
  • a presensitized printing plate comprising a hydrophilic base material having directly coated thereon a layer comprising a polyacrylic acid and 2-methoxy-diphenylamine-4-diazonium bromide.
  • a presensitized printing plate comprising a hydrophilic base material having directly coated thereon a layer comprising a polyacrylic acid and 4-methoxy-diphenylamine-4-diazonium bromide.
  • a process for developing a printing plate which comprises exposing to light under a master a presensitized printing plate comprising a hydrophilic base mate- 1Q rial having directed coated thereon a layer comprising a polyacrylic acid and diphenylamine-4-diazonium chloride, and washing the exposed plate with water.
  • a process for developing a printing plate which comprises exposing to light under a master a presensitized printing plate comprising a hydrophilic base material having directly coated thereon a layer comprising a polyacrylic acid and diphenylamine-4-diazonium bromide, and washing the exposed plate with water.
  • a process for developing a printing plate which comprises exposing tov light under a master a presensitized printing plate comprising a hydrophilic base material having directly coated thereon a layer comprising a polyacrylic acid and 4'-bromo-diphenylamine-4-diazoniurn chloride, and washing the exposed plate with water.
  • a process for developing a printing plate which comprises exposing to light under a master a presensitized printing plate comprising a hydrophilic base material having directed coated thereon a layer comprising a polyacrylic acid and 4'-chloro-diphenyl-amine-4-diazonium chloride, and washing the exposed plate with water.
  • a process for developing a printing plate which comprises exposing to light under a master a presensitized printing plate comprising a hydrophilic base material having directly coated thereon a layer comprising a polyacrylic acid and 2-anilido-su1fonyl-diphenylamine-4-diazonium chloride, and washing the exposed plate with water.
  • a process for developing a printing plate which comprises exposing to light under a master a presensitized printing plate comprising a hydrophilic base material having directly coated thereon a layer comprising a polyacrylic acid and 2-(p-toluene-sulfonyl-amino)-diphenylamine-4-diazonium chloride, and washing the exposed plate with water.
  • a process for developing a printing plate which comprises exposing to light under a master a presensitized printing plate comprising a hydrophilic base material having directly coated thereon a layer comprising a polyacrylic acid and 4'-bromo-diphenylamine-4-diazonium bromide, and washing the exposed plate with water.
  • a process for developing a printing plate which comprise exposing to light under a master a presensitized printing plate comprising a hydrophilic base material having directly coated thereon a layer comprising a polyacrylic acid and 4'-chloro-diphenylamine-4-diazonium bromide, and washing the exposed plate with water.
  • a process for developing a printing plate which comprises exposing to light under a master presensitized printing plate comprising a hydrophilic base material havingdirectly coated thereon a layer comprising a polyacrylic acid and 4'-methoxy-diphenylamine-4-diazonium bromide, and washing the exposed plate with water.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Printing Plates And Materials Therefor (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US709185A 1956-12-28 1958-01-16 Diazo printing plates and method for the production thereof Expired - Lifetime US3061429A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DEK30699A DE1055957B (de) 1956-12-28 1956-12-28 Lichtempfindliche Kopierschichten zur Herstellung von Flachdruckformen von hoher mechanischer Widerstandsfaehigkeit
DEK32553A DE1059766B (de) 1956-12-28 1957-07-27 Lichtempfindliches Kopiermaterial zur Herstellung von Flachdruckformen von hoher mechanischer Widerstandsfaehigkeit
DEK0033078 1957-10-05

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US3061429A true US3061429A (en) 1962-10-30

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US709185A Expired - Lifetime US3061429A (en) 1956-12-28 1958-01-16 Diazo printing plates and method for the production thereof
US763427A Expired - Lifetime US3062644A (en) 1956-12-28 1958-09-26 Diazo printing plates and method for the production thereof

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US (2) US3061429A (nl)
BE (2) BE565433A (nl)
CH (1) CH373641A (nl)
DE (3) DE1055957B (nl)
FR (1) FR1245548A (nl)
GB (1) GB824148A (nl)
NL (2) NL102798C (nl)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3174860A (en) * 1959-02-26 1965-03-23 Azoplate Corp Light sensitive polymeric diazonium and azidoacrylamido reproduction material and process of making plates therewith
US3179518A (en) * 1961-10-13 1965-04-20 Azoplate Corp Presensitized printing foil having as a coating thereon a light-sensitive diazo compound with polyvinyl phosphonic acid
US3219447A (en) * 1961-01-25 1965-11-23 Azoplate Corp Material for the photo mechanical manufacture of printing plates and method for converting the same into printing plates
US3235384A (en) * 1960-10-07 1966-02-15 Azoplate Corp Reproduction layers for planographic and offset printing plates
US3510307A (en) * 1965-01-02 1970-05-05 Kalle Ag Process for the preparation of a printing plate presensitized with a diazonium salt
US4539285A (en) * 1984-03-14 1985-09-03 American Hoechst Corporation Photosensitive negative diazo composition with two acrylic polymers for photolithography
US4731316A (en) * 1984-10-12 1988-03-15 Mitsubishi Chemical Industries Limited Photosensitive composition

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3284198A (en) * 1963-09-11 1966-11-08 Martin Marietta Corp Method for making photolithographic plate
GB1170495A (en) * 1967-03-31 1969-11-12 Agfa Gevaert Nv Radiation-Sensitive Recording Material
US4407862A (en) 1978-03-31 1983-10-04 W. R. Grace & Co. Method of making letterpress printing plates
US4387469A (en) * 1980-06-03 1983-06-07 Clarion Co., Ltd. Tuner control system
US5002856A (en) * 1989-08-02 1991-03-26 E. I. Du Pont De Nemours And Company Thermally stable carbazole diazonium salts as sources of photo-initiated strong acid
US5219711A (en) * 1990-04-10 1993-06-15 E. I. Du Pont De Nemours And Company Positive image formation utilizing resist material with carbazole diazonium salt acid generator
US4985332A (en) * 1990-04-10 1991-01-15 E. I. Du Pont De Nemours And Company Resist material with carbazole diazonium salt acid generator and process for use
EP0737894B1 (en) * 1995-02-15 2000-06-07 Agfa-Gevaert N.V. A diazo based imaging element having improved storage stability

Citations (8)

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US2063631A (en) * 1932-05-23 1936-12-08 Kalle & Co Ag Diazo compounds and a process of preparing them
US2649373A (en) * 1948-10-18 1953-08-18 Warren S D Co Paper printing foils for lithographic purposes and a process of preparing them
US2667415A (en) * 1948-10-15 1954-01-26 Azoplate Corp Process for producing positive photolithographic printing foils
US2687958A (en) * 1949-05-14 1954-08-31 Azoplate Corp Light-sensitive layers for the printing industry
US2720467A (en) * 1951-09-11 1955-10-11 Ozalid Co Ltd Process for preparing photographic elements
US2760431A (en) * 1952-06-19 1956-08-28 Dick Co Ab Lithographic plates and methods for manufacturing same
US2772974A (en) * 1954-02-10 1956-12-04 Gen Aniline & Film Corp Light sensitive diazotype materials
US2937085A (en) * 1954-01-11 1960-05-17 Ditto Inc Composite photosensitive plate, and method of making printing plate therefrom

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2531485A (en) * 1947-04-02 1950-11-28 Gen Aniline & Film Corp Diazotypes comprising amine salts of sulfonic acid containing azo components
US2593928A (en) * 1947-10-09 1952-04-22 Gen Aniline & Film Corp Dimensionally stable diazotype photographic film and process for making it
DE838699C (de) * 1949-10-10 1952-05-12 Kalle & Co Ag Verfahren zur Herstellung von Gerbbildern von hoher mechanischer Widerstandsfaehigkeit
NL188976B (nl) * 1954-02-10 Van Der Lely Nv C Maaimachine.

Patent Citations (8)

* 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
US2667415A (en) * 1948-10-15 1954-01-26 Azoplate Corp Process for producing positive photolithographic printing foils
US2649373A (en) * 1948-10-18 1953-08-18 Warren S D Co Paper printing foils for lithographic purposes and a process of preparing them
US2687958A (en) * 1949-05-14 1954-08-31 Azoplate Corp Light-sensitive layers for the printing industry
US2720467A (en) * 1951-09-11 1955-10-11 Ozalid Co Ltd Process for preparing photographic elements
US2760431A (en) * 1952-06-19 1956-08-28 Dick Co Ab Lithographic plates and methods for manufacturing same
US2937085A (en) * 1954-01-11 1960-05-17 Ditto Inc Composite photosensitive plate, and method of making printing plate therefrom
US2772974A (en) * 1954-02-10 1956-12-04 Gen Aniline & Film Corp Light sensitive diazotype materials

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3174860A (en) * 1959-02-26 1965-03-23 Azoplate Corp Light sensitive polymeric diazonium and azidoacrylamido reproduction material and process of making plates therewith
US3235384A (en) * 1960-10-07 1966-02-15 Azoplate Corp Reproduction layers for planographic and offset printing plates
US3219447A (en) * 1961-01-25 1965-11-23 Azoplate Corp Material for the photo mechanical manufacture of printing plates and method for converting the same into printing plates
US3179518A (en) * 1961-10-13 1965-04-20 Azoplate Corp Presensitized printing foil having as a coating thereon a light-sensitive diazo compound with polyvinyl phosphonic acid
US3510307A (en) * 1965-01-02 1970-05-05 Kalle Ag Process for the preparation of a printing plate presensitized with a diazonium salt
US4539285A (en) * 1984-03-14 1985-09-03 American Hoechst Corporation Photosensitive negative diazo composition with two acrylic polymers for photolithography
US4731316A (en) * 1984-10-12 1988-03-15 Mitsubishi Chemical Industries Limited Photosensitive composition

Also Published As

Publication number Publication date
DE1059766B (de) 1959-06-18
US3062644A (en) 1962-11-06
CH373641A (de) 1963-11-30
FR1245548A (fr) 1960-11-10
GB824148A (en) 1959-11-25
BE565433A (nl)
NL231268A (nl)
DE1055957B (de) 1959-04-23
BE571292A (nl)
NL102798C (nl)
DE1067307B (nl)

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