US3061429A - Diazo printing plates and method for the production thereof - Google Patents
Diazo printing plates and method for the production thereof Download PDFInfo
- 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
- Authority
- US
- United States
- Prior art keywords
- diphenylamine
- diazonium
- printing plate
- polyacrylic acid
- layer
- 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 - Lifetime
Links
- 238000007639 printing Methods 0.000 title claims description 77
- 238000000034 method Methods 0.000 title description 30
- 238000004519 manufacturing process Methods 0.000 title description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title 1
- 229920002125 Sokalan® Polymers 0.000 claims description 58
- 239000012954 diazonium Substances 0.000 claims description 58
- 239000004584 polyacrylic acid Substances 0.000 claims description 57
- 239000000463 material Substances 0.000 claims description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 33
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 11
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 claims description 7
- 239000002585 base Substances 0.000 description 41
- 239000000243 solution Substances 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 239000011888 foil Substances 0.000 description 25
- 238000005406 washing Methods 0.000 description 20
- 125000001309 chloro group Chemical group Cl* 0.000 description 18
- 150000008049 diazo compounds Chemical class 0.000 description 13
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 12
- 239000000084 colloidal system Substances 0.000 description 12
- 229910052782 aluminium Inorganic materials 0.000 description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- -1 DIAZO Chemical class 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 150000002431 hydrogen Chemical group 0.000 description 4
- 238000007645 offset printing Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000978776 Senegalia senegal Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001649 bromium compounds Chemical class 0.000 description 2
- 230000001680 brushing effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical group 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- ZRDSGWXWQNSQAN-UHFFFAOYSA-N 6-diazo-n-phenylcyclohexa-2,4-dien-1-amine Chemical class [N-]=[N+]=C1C=CC=CC1NC1=CC=CC=C1 ZRDSGWXWQNSQAN-UHFFFAOYSA-N 0.000 description 1
- PWSJRIAOUKLSMX-UHFFFAOYSA-N Cl[N+](Cl)=[N-] Chemical class Cl[N+](Cl)=[N-] PWSJRIAOUKLSMX-UHFFFAOYSA-N 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N N-phenyl aniline Natural products C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910000318 alkali metal phosphate Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005615 azonium group Chemical group 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
- 210000005053 lamin Anatomy 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
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.
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Printing Plates And Materials Therefor (AREA)
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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3061429A true US3061429A (en) | 1962-10-30 |
Family
ID=27211138
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US763427A Expired - Lifetime US3062644A (en) | 1956-12-28 | 1958-09-26 | Diazo printing plates and method for the production thereof |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US3061429A (en, 2012) |
| BE (2) | BE565433A (en, 2012) |
| CH (1) | CH373641A (en, 2012) |
| DE (3) | DE1055957B (en, 2012) |
| FR (1) | FR1245548A (en, 2012) |
| GB (1) | GB824148A (en, 2012) |
| NL (2) | NL102798C (en, 2012) |
Cited By (7)
| 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)
| 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 |
| 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 |
| 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 |
| EP0737894B1 (en) * | 1995-02-15 | 2000-06-07 | Agfa-Gevaert N.V. | A diazo based imaging element having improved storage stability |
Citations (8)
| 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 |
| 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)
| 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. |
-
0
- NL NL231268D patent/NL231268A/xx unknown
- DE DENDAT1067307D patent/DE1067307B/de active Pending
- BE BE571292D patent/BE571292A/xx unknown
- NL NL102798D patent/NL102798C/xx active
- BE BE565433D patent/BE565433A/xx unknown
-
1956
- 1956-12-28 DE DEK30699A patent/DE1055957B/de active Pending
-
1957
- 1957-07-27 DE DEK32553A patent/DE1059766B/de active Pending
- 1957-12-20 GB GB39608/57A patent/GB824148A/en not_active Expired
- 1957-12-27 FR FR754716A patent/FR1245548A/fr not_active Expired
-
1958
- 1958-01-16 US US709185A patent/US3061429A/en not_active Expired - Lifetime
- 1958-09-05 CH CH6364358A patent/CH373641A/de unknown
- 1958-09-26 US US763427A patent/US3062644A/en not_active Expired - Lifetime
Patent Citations (8)
| 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)
| 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 |
|---|---|
| DE1055957B (de) | 1959-04-23 |
| GB824148A (en) | 1959-11-25 |
| FR1245548A (fr) | 1960-11-10 |
| NL102798C (en, 2012) | |
| NL231268A (en, 2012) | |
| DE1059766B (de) | 1959-06-18 |
| US3062644A (en) | 1962-11-06 |
| BE565433A (en, 2012) | |
| BE571292A (en, 2012) | |
| DE1067307B (en, 2012) | |
| CH373641A (de) | 1963-11-30 |
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