US2772972A - Positive diazotype printing plates - Google Patents

Positive diazotype printing plates Download PDF

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Publication number
US2772972A
US2772972A US451271A US45127154A US2772972A US 2772972 A US2772972 A US 2772972A US 451271 A US451271 A US 451271A US 45127154 A US45127154 A US 45127154A US 2772972 A US2772972 A US 2772972A
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Prior art keywords
plate
diazo
parts
layer
resin
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US451271A
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English (en)
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Jr Clifford E Herrick
Jr Peter T Woitach
Edward J Trojnar
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GAF Chemicals Corp
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General Aniline and Film Corp
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Priority to NL199728D priority Critical patent/NL199728A/xx
Priority to NL95407D priority patent/NL95407C/xx
Priority to BE540225D priority patent/BE540225A/xx
Priority to US451271A priority patent/US2772972A/en
Application filed by General Aniline and Film Corp filed Critical General Aniline and Film Corp
Priority to GB15451/55A priority patent/GB784001A/en
Priority to FR1134857D priority patent/FR1134857A/fr
Priority to DEG17721A priority patent/DE1108079B/de
Priority to CH347712D priority patent/CH347712A/de
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Publication of US2772972A publication Critical patent/US2772972A/en
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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
    • G03F7/022—Quinonediazides

Definitions

  • the present invention relates to a pre-sensitized, positive-Working, offset printing plate derived from a plate having a hydrophobic resinous layer sensitized with,.a diazonium compound, said resinous layer being capable of being rendered hydrophilic, after exposure of the plate, at the light-struck portions of the same, and to the preparation and processing of .such a plate.
  • the dia'zotype process is ideal. This process, as is understood, involves the sensitizationV of a base with a light-sensitive diazonium compound, the exposure of the sensitive element under a pattern, and the treatment of the element with a base in the presence of a coupling component to produce an azo dye in those portions where the sensitized element has not been struck by light.
  • any printed, drawn or written material on a from-translucent-to-transparent base serves as a master for the diazotype process.
  • the offset printing method is especially interesting since the copies prepared using the offset press possess several advantages over competitive processes.
  • the image produced by the offset press is composed of a permanent carbon pigment, while. the image in a diazotype or spirit reproduction is composed of dye which in time may fade.
  • the non-image areas contain photodecomposition ⁇ products which are prone -As a matter of fact, matterr appear- ⁇ to cause a yellow discoloration, especially if the print be exposed to strong light.
  • stability against premature color formation in diazotype papers is brought about through the use of a heavy load of ac id in the sensitive layer and some loss of strength of the paper may occur on aging.
  • the quality of the ⁇ printing produced by thevoifset press is outstanding.
  • the use of the offset press has heretofore involved either the manual recopying of an original onto asocalled direct image master plate or the use of expensive, light-sensitive masterplates either negative-working or positive-working.
  • the preparation of master plates usinga negative-working, photosensitive offset plate involves several time-consuming operations and expensive photographic equipment* so-called legitimate graphic arts eld, where the requirements of exceptionally high printingnquality, absolute dimensional stability and long runs justify the use c-f a.
  • a suitable substrate for instancepaper
  • a suitable substrate for instancepaper
  • a resinous co-polymer of about one mol of a vinyl compound with about one mol of an ethenoid dicarboxylic. acid compound and a hydrophobic resin cornpatible with said co-polymer.
  • these materials are ⁇ hydrophobic and areunreceptive to water or water miscible substances.
  • Hydrophilic character may be imparted by treating the, coated surface with an alkali such .as sodium orammoniurn hydroxide and the like.
  • a mixture of about 60 parts by weight of such a co-polymer and about 40% by weight of a low viscosity cellulose acetate is lacquered onto paper and then rendered hydrophilic with a 5% aqueous solution of ethanolamine.
  • An excess of such aqueous solution is advantageously applied and after a suitable imbition time, amounting to several seconds, is removed with an air knife.
  • Such a layer may be sensitized with a water-so-luble, negative-Working sensitizer such as is described in German patent application Kl67,l30, referred to in PB 1308, page 48, and satisfactory negativeworking plates thus obtained.
  • a water-insoluble, solvent-soluble, alkali-resistant adhesive resin in the sensitizing formulation as, for instance, a low molecular weight vinyl polymer, i. e., polyvinyl acetate.
  • a strongly adherent surface coating is 'obtained by sensitizing the hydrophobic surface while using, for example, methyl isobutyl ketone as a solvent, low viscosity, completely acetylated polyvinyl acetate as an adhesive resin and 2-diazo-1-naphthol- S-ethylsulfonate as the sensitizer.
  • the sensitizing layer in the exposed regions of such a plate can be removed completely and easily by treating the entire surface of the plate with a solution comprising an aliphatic polyhydroxy compound.
  • the unexposed parts of the sensitizing layer resist the action of such processing reagent and remain behind.
  • hydrophilic character can be introduced into the layer comprising PVM/ MA by the careful use of one of the methods described in the aforesaid patent application.
  • great advantages accrue if hydrophilic character be imparted to the PVM/MA layer by treatment with an amine, preferably an alkylolamine.
  • Our invention envisages an article capable of conversion to a positive-working, oiset printing plate comprising an inexpensive base vmaterial bearing a hydrophobic lacquer layer comprising essentially PVM/MA, said lacquer layer being coated with a water-insoluble, solvent-soluble, alkali-resistant adhesive resin and a lightsensitive diazo oxide and the processing of such article to a printing plate by exposure under a pattern, the removal of the outer layer where exposed by an aliphatic polyhydroxy compound and the imparting of hydrophilic character to the lacquer layer by use of an alkylolamine at those points where the outer layer has been removed.
  • Such article, the preparation of the same, the processing thereof to form a positive offset printing plate and such plate constitute the purposes and objects of the present invention.
  • the raw plate comprises a base 1 bearing a lacquer substratum 2 having an outer coating 3 of an adhesive resin and a light-sensitive diazo compound.
  • the base 1 of such a plate is made of a relativelyinexpensive fibrous material, such as paper, cloth or the like.
  • a relativelyinexpensive fibrous material such as paper, cloth or the like.
  • a base such as is described in U. S. P. 2,534,588 granted December 19, 1950, ⁇ or a wet strength clay-casein surfaced paper. It will be apparent, however, that the specific nature of this base material is not a critical feature of the invention since any relatively inexpensive fibrous material capable of accepting and retaining the lacquer layer 2 is suitable.
  • the lacquer layer 2 contains as its essential element a l.zo-polymer of vinyl methyl ether and maleic anhydride (PVM/MA) in substantially equi-molar proportions.
  • PVM/MA vinyl methyl ether and maleic anhydride
  • the layer 2 consists of PVM/MA
  • the layer 2 is composed of a solid solution of PVM/MA and a hydrophobic resin compatible therewith.
  • the hydrophobic resin serves the functions of imparting toughness and exibilityto the plate and of eliminating tendencies of the layer 2 to crack or craze.
  • a hydrophobic resin may be present in the lacquer layer 2 in a quantity as high as 60% of the lacquer layer. For best results, however, the quantity of the hydrophobic resin should not exceed 40% by weight of the solid contents of the lacquer layer 2.
  • the llacquer layer exists as a solid solution of PVM/MA and said hydrophobic resin,fwhi'ch1.is compatiblewwithlthe PVM/MA.
  • Compatability of the resins is,- ⁇ of course, a.
  • Acondition precedent ⁇ to Ithe obtainof a true ⁇ solicl solution and not a heterogeneous mixture of the resins. It is manifest that the latter ⁇ would offer a variable surface to the processing solutionspthusleading to nonuniformity in the creation of; hydrophilic character in said layer.
  • Hydrophobic resins compatible with thei-co-polymer includewthe various vcellulose esters-such as cellulose acetate, cellulose propionate, ⁇ cellulose butyrate, the mixed esters such as celluloseacetatepropionate, celluloseacetatebutyrate and thel like,.polyvinyl resins such ⁇ as polyvinylacetate, polyvinylacetals' such as polyvinylbutyral, methylacrylate, methylmethacrylate and the like.
  • grades which contain combined acetic acid from as low as 52% to as high as 61.8%k (triacetate) can be employed.
  • a cellulose esteri bebused, ⁇ it is recommended that it be of lhigh acyl content. --We have good reason to believe that since-'the maleic anhydride copolymers are reactive materials, they can, in the course of time, react with the unesteried hydroxyls of a low acyl ester. The result of such a reaction is usually a change in the degree-to which the layer can be rendered hydrophilic. Thus, a freshlyl lacquered sample containing a low acyl cellulose ester ⁇ may respond dilerently to the processing solution than a sample some weeks old.
  • hydrophobic resins the use of which we contemplate, are all commercial materials, the solubility properties -of which are known. vThe same is true of PVM/ MA. It is, therefore, a very simple matter to determine the suitability of any-hydrophobic resinfor use with PVM/MA in forming thelacquer layer 2.
  • solvents and solvent-mixtures may be utilized for laying'down the lacquer coating and,'in this connection, attention is directed to the solvents described in the aforesaid application, Serial No. 265,046.
  • Solvents which we have Ifound to be suitable are liquid relatively low boiling organic solvents such as methyl cellosolve, acetone, methylene chloride,dioxane, ⁇ tetrahydrofurane, cyclohexanone, methylethylketone-and various mixtures of the same.
  • Such mixtures include, for example, methylene chloride, methylcellosolve -and acetone, rnethylcellosolve and dioxane, methylcellosolve and cyclohexanone, methylcellosolve and tetrahydrofurane and the like.
  • This filmf generally has a thickness ranging from about .l -to .4 mil, preferably .2 mil.
  • the outer layer 3 contains as tthe sensitizing component a diazo oxide which is water insoluble but which is soluble to the extent of at least 1% in a solvent which is a liquid and is an aliphatic-ester, an aliphatic ketone or an aliphatic alcohol, i. e., alcohols in which the -OH group is aliphatically linked.
  • a diazo oxide which is water insoluble but which is soluble to the extent of at least 1% in a solvent which is a liquid and is an aliphatic-ester, an aliphatic ketone or an aliphatic alcohol, i. e., alcohols in which the -OH group is aliphatically linked.
  • Diazo oxides within the broad'class which we have found to be particularly suitable are those derivedby esterication or amidation of Z-diazo-l-naphthol-S-sulfonyl chlorides or Z-naphthol-l-diazo-S-sulfonyl chlorides with comparatively simple amines or alcoholsV or ⁇ with more complex compounds which possess a saturated, unconjugated, non-polar molecule such as rosin amines, rosin alcohols andtheir derivatives.
  • R1 isV alkoxy, i. e., methoxy, ethoxy, propoxy, aryloxy such as phenoxy, naphthoxy and the like, ammo such as primary amino, alkyl amino, i. e., methylamino,
  • diazo oxides embraced by these formulae are:
  • the aforementioned diazo oxides excepting for those containing the rosin amine structure, are known compounds and are prepared ⁇ by a simple esterication or amidation of the sulfonyl chloride in the presence of an acid binding yagent such as pyridine.
  • the rosin derivatives are prepared according to the method described .in the application of Ralph G. ⁇ D.
  • the light-sensitive diazo oxide as noted is laid down with an alkali-resistant adhesive resin in order to ensure adequate adhesion of the image to the lacquer layer 2.
  • an alkali-resistant adhesive resin there may be employed any water-insoluble, alkali-resistant resinous material which is soluble in any of the aforementioned limited classes of solvents for the diazo oxide, at least to an extent of 1% by weight.
  • the resin must be resistant to or impervious to the action of aliphatic polyhydroxy compounds and alkylolamines which are utilized in the processing Vof the raw plate to the nshed offset printing plate.
  • the resin should thus withstand a contact time of one-half minute or longer with such reagents and resist removal from the lacquer layer 2 during such period of contact in the absence of the photodecomposition products. It is advantageous but not essential that the resin be of low or moderate molecular weight since such resins have improved adhesive character and are more readily removed in the presence of the photodecomposition products.
  • Figure II of the drawing indicates the condition of the article of Figure l after processing thereof. lt will be observed from Figure II that the outer coating 3 has been locally removed at those areas 4 which were lightstruck. In these areas, the processing solvents have penetrated the lacquer substratum 2, as indicated by reference numeral 5, imparting hydrophilic character thereto, making such areas water attractive.
  • the printing areas 6 of layer 3 which have not been removed or atfected by the processing solutions remain hydrophobic and greasereceptive.
  • the processing of the article of Figure 1 to produce the product of Figure II is brought about by exposure of the plate under a pattern which permits light to pass where the patternV is transparent or translucent and which blocks the passage of light where the pattern is opaque. Where the light strikes the plate, decomposition of the diazo oxide ensues.
  • the photodecomposition products of the ⁇ diazo oxide are soluble or swellable in liquid aliphatic polyhydroxy compounds, thus permitting the selective removal of the photodecomposition products and thc adhesive resin commingled therewith from the lacquer layer 2.
  • the polyhydroxy compound utilized for removal of the decomposition products and the adhesive resin is any liquid aliphatic polyhydroxy compound such as the various alkyl glycols, i. e., ethylene glycol, propylene glycol, diethylene glycol, l-3-butylene glycol, 2-3-butyleneglycol, dipropylene glycol, hexylene glycol, trihydric alcohols such as glycerin and the like.
  • Such polyhydroxy compounds may be used alone or in admixture and as suitable mixtures we have used ethylene glycol with glycerin, hexylene glycol with glycerin, 2,3-butylene glycol with glycerin, propylene glycol with ethylene glycol and the like. It has been our finding that the solubility or swellability of the diazo oxide photodecomposition products in liquid aliphatic polyhydroxy compounds is a general phenomenon and, hence, any such solvent is suitable for use.
  • alkylolamine any. aliphatic a'lkylol- ⁇ amine Which is soluble in the aforementioned polyhydroxy compounds, preferably .one.having a reactive fhydrogen atom attached tothe amino nitrogen, such as ethanolamine, diethanolamine, propanolamine, di-isopropanol amine, butanolamine, ethanolisopropanolamine, ethanolisobutanolamine and the like.
  • Tertiary alkylolamines such as triethanolarnine,- may Ibe employed but are less effective, which prompted the conclusion previouslyV expressed that the induction of hydrophilic character in the lacquer layer 2 when using a non-tertiary alkylolamine is the result of at least apartial amidation of the carboxy groups in the PVM/ MA.
  • a further important factor of our invention involves the use of our offset plate for reproduction of half-tone originals or the preparation of prints by projecting anY enlarged or reduced image onto the light-,sensitive sur ⁇ face. .
  • the superior results in these applications can be secured by applying to the iibrous base an antihalation coating of a dyestuif of the typeused in the manufacture
  • Example ⁇ I The diazo ⁇ oxide of; ExampleJ, French Patent No.
  • the sensitizing layer is thus rapidly removedV in the regions of the plate which were unprotected during the exposure by opaque portions of the original.
  • the cornpleteness of this removal can be conveniently followed by the presence of color on the exposed surface since the exposed sensitizing layer is brownish in hue.
  • Hydrophilic character is imparted to the resin underlayer by next swabbing the surface of the plate with a solution containing l0 parts of diethanolamine and 90 parts of, glycerin.
  • the plate Before starting the press, the plate is treated with an acidic Platex solution to facilitate ink pickup by the image.
  • Diazo oxides of high molecular weight are not essential. This is contrary to the notion presently advanced that for printing plates it is essential that there be employed diazo oxides ofexcessively high molecular weight.
  • Resins resistant to or stable to alkalies are employed in the sensitized layer.
  • the plate Vconstructed by us shows a distinct improvement over plates previously known or described.
  • Example 1I The procedure is the same asin Example I excepting that the plate after exposure is treated with the following solution:
  • Example IIIY p The procedure is the same as in Example I excepting that coumarone-indene resin is replaced by an equalV weight of a low viscosity polyvinyl acetate such as that sold by Carbide and Carbon Chemicals Corporation under the trademark "Vinylite AYAC.
  • the plate ob tained has characteristics simulating those of Examples I and II.
  • the photoproduct and resin in the exposed areas were removed by swabbing the plate with a solution of l5 parts of isopropanol and 85 parts of ethylene glycol.
  • the nonimage areas were then rendered hydrophilic by treating the plate with a solution of l5 parts of diethanolamine and 85 parts of ethylene glycol.
  • the plate was then treated with the conventional acidic press solution and printing was started. In excess of 500 excellent copies were obtained.
  • Example IV The procedure is the same as in Example IV excepting that the plate directly after exposure was treated with a solution containing l5 parts of diethanolamine and 85 parts of ethylene glycol, the plate thereby being rendered ready for printing.
  • Example VI The procedure is the same as in .Example IV except-' ing that the plate directly after exposure was treated with a soution containing 2 parts of monoethanol amine and 98 parts of ethylene glycol. The plate so processed yielded over 590 copies of excellent fidelity.
  • Example VII A paper base was lacquered and sensitized as in Example lV except that the polyvinyl acetate in the sensitizing solution was replaced by an equal amount of a methyl acrylate polymer (marketed by Rohm and Hass Company, Philadelphia, Pa., under the trademark Acryloid C-l0).
  • a methyl acrylate polymer marketed by Rohm and Hass Company, Philadelphia, Pa., under the trademark Acryloid C-l0.
  • the plate was treated with ethylene glycol, the photoproduct and resin thereby being removed in the nonimage areas.
  • a solution containing 85 parts of ethylene glycol and 15 parts of diethanolamine was applied. When put on the os'et press, ovel 500 excellent positive copies were obtained.
  • any of the following solutions may be used to remove photoproduct and resin from the non-image areas:
  • Example VIII Av paper base was lacquered as ⁇ in Example I. The dried, lacquered base was then sensitized by bead-coating with a solution of the following composition:
  • the dried, sensitized plate was then exposed beneath a positive original, andtreated with a solution composed of parts of ethylene glycol and l5 parts of diacetone alcohol. A positive yellow image upon a white background was obtained(v).
  • the plate was then rendered hydrophilic in the non-image areas by treatment with a solution of l5 parts of diethanolamine in 85 parts of ethylene glycol. Theplate was now inked.v Over 500 excellent positive copies were obtained.
  • Example IX The procedure is the same as in Example VIII excepting that the plate directly after exposure was readied for printing by treatment with a solution composed of 72 parts of ethylene glycol, 13 parts of diethanolamine and l5 parts of diacetone alcohol. Over 500 excellent copies were obtained.
  • Example A paper base was lacquered as in Example I.
  • the dried, lacquered base was then sensitized by bead-coating with a solution containing:
  • Example XI The procedure was the same as in Example X excepting that the plate after exposure was directly readied for printing by treatment withV a solution containing:
  • Example XII A lacquered paper base prepared as in Example l '1113 was sensitized, by .bead-coating with a solution .of the following composition:
  • Example XIII A lacquered paper prepared as in Example I was beadcoated with -a solution having the following composition:
  • Example XIV The clay-casein surface layer of the paper base as described in Example I was provided withgan antihalation coating by impregnating it with a solution containing 4 parts of Fast Light Red BA, 2 parts of Diazo Fast Yellow in 100 parts of water. After drying, the pinkorange surface was lacquer-coated and sensitized as in Example IV.
  • the sensitized plate was exposed to a 35-ampere carbon arc at a, distance of 3 feet for 45 seconds beneath a screened film positive (133 lines per inch).
  • the exposed plate was treated with a solution containing S parts of ethylene glycol and 15 parts of diethanolamine, then treated with Platex, and copies run on the offset l dried,lacquered base was then sensitized by bead-coating with the following solution:
  • Example XVI The procedure is the same as in Example X excepting that the high acetyl, high viscosity, cellulose kacetate employed to form the'lacquer layer 2 is replaced by an Several aluminum offset plates having a surfaceprepared according to the teachings of U. S. P. 2,637,929
  • Positive-working metal plates manufactured by the Azo- Plate Corporation of Summit, New Jersey were exposed using the above original at several different exposure times and then processed with the reagents furnished bythe manufacturer.
  • Example IV Polyvinylacetate used in Example IV was coated alone from methyl isobutyl ketone on the lacquer base of said example. The dried coated plate was then treated with the ethylene-glycol isopropanol mixture of said example but it was found that the resin layer was not removed. An attempt was made to render the plate hydrophilic with the diethanolamine-ethylene glycol mixture of Example IV but the plate failed completely to respond to such treatment, remaining completely hydrophobic and ink-receptive.
  • a plate capable of conversion to an offset printing plate comprising a base, a hydrophobic layer on said base comprising essentially a copolymer of vinyl methyl ether and maleic anhydride on said base and an overcoating on said hydrophobic layer of a water-insoluble, alkali-resistant adhesive resin and a light-sensitive, water-insoluble diazo oxide which is soluble in a solvent selected from the class consisting of liquid aliphatic esters, aliphatic ketones and aliphatic alcohols.
  • a plate capable of conversion to an offset printing plate comprising a base, a layer on said base comprising a solid solution of a co-polymer of vinyl methyl ether and maleic anhydride and a hydrophobic resin compatible therewith, and a coating on said layer of a water-insoluble adhesive resin and a light-sensitive, water-insoluble diazo oxide which is soluble in a solvent selected from the class consisting of liquid aliphatic esters, aliphatic ketones and aliphatic alcohols.
  • diazo oxide is selected from the class consisting of esters and amides of l-diaZo-Z-naphtholand 2-diazo-1-naphtol-5- sulfonic acids.
  • diazo oxide is selected from the class consisting of esters and amides of 1-diazo-2-naphtholand 2-diazo-1-naphthol-5- sulfonic acids.
  • the process of producing a plate capable of conversion to an offset printing plate which comprises coating a base with an organic solvent solution of PVM/ MA, drying the base to form a hydrophobic film essentially comprising PVM/MA and overcoating the film with a solution in an organic solvent selected from the class consisting of a liquid aliphatic ester, an aliphatic ketone boiling above C. and an aliphatic alcohol containing at least four carbon atoms of an alkali-resistant, water-insoluble adhesive resin and a water-insoluble, diazo oxide.
  • the lightsensitive diazo oxide is selected from the class consisting of amides and esters of l-diazo-Z-naphtholand 2-diazo-1- naphthol-S-sulfonic acid.
  • An offset printing plate having grease-receptive printing portions comprising a water-insoluble, alkaliresistant synthetic resin and a water-insoluble, light-sensitive diazo oxide soluble in a liquid solvent selected from the class consisting of aliphatic esters, aliphatic ketones and aliphatic alcohols and water-receptive, non-printing portions essentially comprising PVM/MA rendered hydrophilic by treatment with an alkylalamine.
  • theadhesive resin is selected from the class consisting of cellulose esters and ethers.
  • diazo oxide is selected from the class consisting of esters and amides of l-diazo-Z-naphtholand 2-diazo-l-naphthol-5- sulfonic acid.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Printing Plates And Materials Therefor (AREA)
US451271A 1954-08-20 1954-08-20 Positive diazotype printing plates Expired - Lifetime US2772972A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
NL199728D NL199728A (de) 1954-08-20
NL95407D NL95407C (de) 1954-08-20
BE540225D BE540225A (de) 1954-08-20
US451271A US2772972A (en) 1954-08-20 1954-08-20 Positive diazotype printing plates
GB15451/55A GB784001A (en) 1954-08-20 1955-05-27 Positive diazotype printing plates
FR1134857D FR1134857A (fr) 1954-08-20 1955-07-20 Plaque diazotype positive pour impression offset et procédé pour sa préparation
DEG17721A DE1108079B (de) 1954-08-20 1955-08-04 Vorsensibilisierte, positiv arbeitende Flachdruckfolie
CH347712D CH347712A (de) 1954-08-20 1955-08-17 Zur Herstellung einer Offsetdruckplatte verwendbare lichtempfindliche Platte

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US451271A US2772972A (en) 1954-08-20 1954-08-20 Positive diazotype printing plates

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US2772972A true US2772972A (en) 1956-12-04

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BE (1) BE540225A (de)
CH (1) CH347712A (de)
DE (1) DE1108079B (de)
FR (1) FR1134857A (de)
GB (1) GB784001A (de)
NL (2) NL199728A (de)

Cited By (49)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2993788A (en) * 1958-06-17 1961-07-25 Gen Aniline & Film Corp Multicolor reproduction using light sensitive diazo oxides
US3086861A (en) * 1960-07-01 1963-04-23 Gen Aniline & Film Corp Printing plates comprising ink receptive azo dye surfaces
US3095301A (en) * 1959-04-06 1963-06-25 Gen Aniline & Film Corp Electrophotographic element
US3130051A (en) * 1958-12-10 1964-04-21 Gen Aniline & Film Corp Process for producing negative working offset diazo printing plates
US3136639A (en) * 1957-11-01 1964-06-09 Lithoplate Inc Diazo presensitized lithographic plate base comprising a urea-formaldehyde intermediate layer and process for making
US3136636A (en) * 1950-12-06 1964-06-09 Minnesota Mining & Mfg Planographic printing plate comprising a polyacid organic intermediate layer
US3149972A (en) * 1960-08-16 1964-09-22 Gen Aniline & Film Corp Diazo and resinous coupler printing plates for photomechanical reproduction
US3164468A (en) * 1960-06-06 1965-01-05 Gen Aniline & Film Corp Photomechanical reversal process and foil and dyes for use therein
US3169066A (en) * 1959-01-12 1965-02-09 Hoerner Hans Photomechanical method of producing printing forms
US3173788A (en) * 1960-02-10 1965-03-16 Gen Aniline & Film Corp Developing positive working photolitho-graphic printing plates containing diazo oxides
US3185085A (en) * 1961-01-09 1965-05-25 Gen Aniline & Film Corp Method of adding hydrophobic images to the hydrophilic surface of positive or negative paper offset plates
US3264104A (en) * 1961-07-28 1966-08-02 Azoplate Corp Reversal-development process for reproduction coatings containing diazo compounds
US3402044A (en) * 1963-12-09 1968-09-17 Shipley Co Light-sensitive naphthoquinone diazide composition and material containing an alkali insoluble polymer
US3454424A (en) * 1965-07-30 1969-07-08 Du Pont Process for making photographic films
US3474719A (en) * 1966-04-15 1969-10-28 Gaf Corp Offset printing plates
US3486450A (en) * 1964-02-27 1969-12-30 Eastman Kodak Co Color proofing system
US3544323A (en) * 1966-12-12 1970-12-01 Sumner Williams Inc Diazo compound for lithographic plates
US3549373A (en) * 1966-03-19 1970-12-22 Ricoh Kk Negative-to-positive reversible copy sheet
US3637384A (en) * 1969-02-17 1972-01-25 Gaf Corp Positive-working diazo-oxide terpolymer photoresists
JPS49106830A (de) * 1973-02-10 1974-10-09
US3920455A (en) * 1971-05-28 1975-11-18 Polychrome Corp Light-sensitive compositions and materials with O-naphthoquinone diazide sulfonyl esters
US4038469A (en) * 1973-07-31 1977-07-26 Glaxo Laboratories Limited Aqueous insoluble polymers containing a plurality of diazomethylene groups
WO1979000593A1 (en) * 1978-02-06 1979-08-23 Napp Systems Inc Desensitizing solution and process for treating a diazo photosensitive printing plate
US4207106A (en) * 1973-05-29 1980-06-10 Fuji Photo Film Co., Ltd. Positive working O-quinone diazide photocopying process with organic resin overlayer
WO1982001085A1 (en) * 1980-09-15 1982-04-01 Systems Inc Napp Bilayer photosensitive imaging article
WO1988002878A1 (en) * 1986-10-20 1988-04-21 Macdermid, Incorporated Image reversal system and process
US4889795A (en) * 1987-02-23 1989-12-26 Oki Electric Industry Co., Ltd. Process for forming photoresist pattern using contrast enhancement layer with abietic acid
EP0410606A2 (de) 1989-07-12 1991-01-30 Fuji Photo Film Co., Ltd. Polysiloxane und positiv arbeitende Resistmasse
US5308744A (en) * 1993-03-05 1994-05-03 Morton International, Inc. Source of photochemically generated acids from diazonaphthoquinone sulfonates of nitrobenzyl derivatives
US5314782A (en) * 1993-03-05 1994-05-24 Morton International, Inc. Deep UV sensitive resistant to latent image decay comprising a diazonaphthoquinone sulfonate of a nitrobenzyl derivative
EP0702271A1 (de) 1994-09-06 1996-03-20 Fuji Photo Film Co., Ltd. Positiv arbeitende Druckplatte
EP0770911A1 (de) 1995-10-23 1997-05-02 Fuji Photo Film Co., Ltd. Lichtempfindliches Blatt mit Schichtträger aus Aluminiumlegierung und lichtempfindliches Silberhalogenidmaterial, dass dieses verwendet
EP0852341A1 (de) 1997-01-03 1998-07-08 Sumitomo Bakelite Company Limited Verfahren zur Bebilderung einer photoempfindlichen Harzzusammensetzung
US6045963A (en) * 1998-03-17 2000-04-04 Kodak Polychrome Graphics Llc Negative-working dry planographic printing plate
US6060217A (en) * 1997-09-02 2000-05-09 Kodak Polychrome Graphics Llc Thermal lithographic printing plates
US6063544A (en) * 1997-03-21 2000-05-16 Kodak Polychrome Graphics Llc Positive-working printing plate and method of providing a positive image therefrom using laser imaging
US6071666A (en) * 1996-05-13 2000-06-06 Sumitomo Bakelite Company, Ltd. Positive type photosensitive resin composition and semiconductor device using the same
US6090532A (en) * 1997-03-21 2000-07-18 Kodak Polychrome Graphics Llc Positive-working infrared radiation sensitive composition and printing plate and imaging method
US6117610A (en) * 1997-08-08 2000-09-12 Kodak Polychrome Graphics Llc Infrared-sensitive diazonaphthoquinone imaging composition and element containing non-basic IR absorbing material and methods of use
US6218083B1 (en) 1997-07-05 2001-04-17 Kodak Plychrome Graphics, Llc Pattern-forming methods
US6280899B1 (en) 1996-04-23 2001-08-28 Kodak Polychrome Graphics, Llc Relation to lithographic printing forms
US6296982B1 (en) 1999-11-19 2001-10-02 Kodak Polychrome Graphics Llc Imaging articles
US6420087B1 (en) 1996-10-31 2002-07-16 Kodak Polychrome Graphics Llc Direct positive lithographic plate
US20040023147A1 (en) * 2000-10-31 2004-02-05 Takashi Hirano Positive photosensitive resin composition, process for its preparation, and semiconductor devices
US20070154843A1 (en) * 2004-01-20 2007-07-05 Asahi Kasei Emd Corporation Resin and resin composition
WO2008020573A1 (fr) 2006-08-15 2008-02-21 Asahi Kasei Emd Corporation Composition de résine photosensible positive
US8742059B2 (en) 2005-03-31 2014-06-03 Dai Nippon Printing Co., Ltd. Polymer precursor, high transparency polyimide precursor, polymer compound, resin composition and article using thereof
US10831101B2 (en) 2016-03-31 2020-11-10 Asahi Kasei Kabushiki Kaisha Photosensitive resin composition, method for manufacturing cured relief pattern, and semiconductor apparatus
CN112142613A (zh) * 2020-09-22 2020-12-29 江南大学 一种松香基小分子有机凝胶剂及其形成的环己烷凝胶

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US3136636A (en) * 1950-12-06 1964-06-09 Minnesota Mining & Mfg Planographic printing plate comprising a polyacid organic intermediate layer
US3136639A (en) * 1957-11-01 1964-06-09 Lithoplate Inc Diazo presensitized lithographic plate base comprising a urea-formaldehyde intermediate layer and process for making
US2993788A (en) * 1958-06-17 1961-07-25 Gen Aniline & Film Corp Multicolor reproduction using light sensitive diazo oxides
US3130051A (en) * 1958-12-10 1964-04-21 Gen Aniline & Film Corp Process for producing negative working offset diazo printing plates
US3169066A (en) * 1959-01-12 1965-02-09 Hoerner Hans Photomechanical method of producing printing forms
US3095301A (en) * 1959-04-06 1963-06-25 Gen Aniline & Film Corp Electrophotographic element
US3173788A (en) * 1960-02-10 1965-03-16 Gen Aniline & Film Corp Developing positive working photolitho-graphic printing plates containing diazo oxides
US3164468A (en) * 1960-06-06 1965-01-05 Gen Aniline & Film Corp Photomechanical reversal process and foil and dyes for use therein
US3086861A (en) * 1960-07-01 1963-04-23 Gen Aniline & Film Corp Printing plates comprising ink receptive azo dye surfaces
US3149972A (en) * 1960-08-16 1964-09-22 Gen Aniline & Film Corp Diazo and resinous coupler printing plates for photomechanical reproduction
US3185085A (en) * 1961-01-09 1965-05-25 Gen Aniline & Film Corp Method of adding hydrophobic images to the hydrophilic surface of positive or negative paper offset plates
US3264104A (en) * 1961-07-28 1966-08-02 Azoplate Corp Reversal-development process for reproduction coatings containing diazo compounds
US3402044A (en) * 1963-12-09 1968-09-17 Shipley Co Light-sensitive naphthoquinone diazide composition and material containing an alkali insoluble polymer
US3486450A (en) * 1964-02-27 1969-12-30 Eastman Kodak Co Color proofing system
US3454424A (en) * 1965-07-30 1969-07-08 Du Pont Process for making photographic films
US3549373A (en) * 1966-03-19 1970-12-22 Ricoh Kk Negative-to-positive reversible copy sheet
US3474719A (en) * 1966-04-15 1969-10-28 Gaf Corp Offset printing plates
US3544323A (en) * 1966-12-12 1970-12-01 Sumner Williams Inc Diazo compound for lithographic plates
US3637384A (en) * 1969-02-17 1972-01-25 Gaf Corp Positive-working diazo-oxide terpolymer photoresists
US3920455A (en) * 1971-05-28 1975-11-18 Polychrome Corp Light-sensitive compositions and materials with O-naphthoquinone diazide sulfonyl esters
JPS49106830A (de) * 1973-02-10 1974-10-09
JPS521663B2 (de) * 1973-02-10 1977-01-17
US4207106A (en) * 1973-05-29 1980-06-10 Fuji Photo Film Co., Ltd. Positive working O-quinone diazide photocopying process with organic resin overlayer
US4038469A (en) * 1973-07-31 1977-07-26 Glaxo Laboratories Limited Aqueous insoluble polymers containing a plurality of diazomethylene groups
WO1979000593A1 (en) * 1978-02-06 1979-08-23 Napp Systems Inc Desensitizing solution and process for treating a diazo photosensitive printing plate
US4329422A (en) * 1978-02-06 1982-05-11 Napp Systems (Usa), Inc. Post-exposure treating solution for photosensitive graphic arts articles
WO1982001085A1 (en) * 1980-09-15 1982-04-01 Systems Inc Napp Bilayer photosensitive imaging article
WO1988002878A1 (en) * 1986-10-20 1988-04-21 Macdermid, Incorporated Image reversal system and process
US4889795A (en) * 1987-02-23 1989-12-26 Oki Electric Industry Co., Ltd. Process for forming photoresist pattern using contrast enhancement layer with abietic acid
EP0410606A2 (de) 1989-07-12 1991-01-30 Fuji Photo Film Co., Ltd. Polysiloxane und positiv arbeitende Resistmasse
US5308744A (en) * 1993-03-05 1994-05-03 Morton International, Inc. Source of photochemically generated acids from diazonaphthoquinone sulfonates of nitrobenzyl derivatives
US5314782A (en) * 1993-03-05 1994-05-24 Morton International, Inc. Deep UV sensitive resistant to latent image decay comprising a diazonaphthoquinone sulfonate of a nitrobenzyl derivative
EP0702271A1 (de) 1994-09-06 1996-03-20 Fuji Photo Film Co., Ltd. Positiv arbeitende Druckplatte
EP0770911A1 (de) 1995-10-23 1997-05-02 Fuji Photo Film Co., Ltd. Lichtempfindliches Blatt mit Schichtträger aus Aluminiumlegierung und lichtempfindliches Silberhalogenidmaterial, dass dieses verwendet
US6485890B2 (en) 1996-04-23 2002-11-26 Kodak Polychrome Graphics, Llc Lithographic printing forms
US6280899B1 (en) 1996-04-23 2001-08-28 Kodak Polychrome Graphics, Llc Relation to lithographic printing forms
US6235436B1 (en) 1996-05-13 2001-05-22 Sumitomo Bakelite Company Limited Semiconductor device using positive photosensitive resin composition and process for preparation thereof
US6071666A (en) * 1996-05-13 2000-06-06 Sumitomo Bakelite Company, Ltd. Positive type photosensitive resin composition and semiconductor device using the same
US6420087B1 (en) 1996-10-31 2002-07-16 Kodak Polychrome Graphics Llc Direct positive lithographic plate
EP0852341A1 (de) 1997-01-03 1998-07-08 Sumitomo Bakelite Company Limited Verfahren zur Bebilderung einer photoempfindlichen Harzzusammensetzung
US6063544A (en) * 1997-03-21 2000-05-16 Kodak Polychrome Graphics Llc Positive-working printing plate and method of providing a positive image therefrom using laser imaging
US6090532A (en) * 1997-03-21 2000-07-18 Kodak Polychrome Graphics Llc Positive-working infrared radiation sensitive composition and printing plate and imaging method
US6218083B1 (en) 1997-07-05 2001-04-17 Kodak Plychrome Graphics, Llc Pattern-forming methods
US6117610A (en) * 1997-08-08 2000-09-12 Kodak Polychrome Graphics Llc Infrared-sensitive diazonaphthoquinone imaging composition and element containing non-basic IR absorbing material and methods of use
US6060217A (en) * 1997-09-02 2000-05-09 Kodak Polychrome Graphics Llc Thermal lithographic printing plates
US6045963A (en) * 1998-03-17 2000-04-04 Kodak Polychrome Graphics Llc Negative-working dry planographic printing plate
US6296982B1 (en) 1999-11-19 2001-10-02 Kodak Polychrome Graphics Llc Imaging articles
US20040023147A1 (en) * 2000-10-31 2004-02-05 Takashi Hirano Positive photosensitive resin composition, process for its preparation, and semiconductor devices
US6908717B2 (en) 2000-10-31 2005-06-21 Sumitomo Bakelite Company Limited Positive photosensitive resin composition, process for its preparation, and semiconductor devices
US20070154843A1 (en) * 2004-01-20 2007-07-05 Asahi Kasei Emd Corporation Resin and resin composition
US7416822B2 (en) * 2004-01-20 2008-08-26 Asahi Kasei Emd Corporation Resin and resin composition
US8742059B2 (en) 2005-03-31 2014-06-03 Dai Nippon Printing Co., Ltd. Polymer precursor, high transparency polyimide precursor, polymer compound, resin composition and article using thereof
WO2008020573A1 (fr) 2006-08-15 2008-02-21 Asahi Kasei Emd Corporation Composition de résine photosensible positive
US10831101B2 (en) 2016-03-31 2020-11-10 Asahi Kasei Kabushiki Kaisha Photosensitive resin composition, method for manufacturing cured relief pattern, and semiconductor apparatus
CN112142613A (zh) * 2020-09-22 2020-12-29 江南大学 一种松香基小分子有机凝胶剂及其形成的环己烷凝胶
CN112142613B (zh) * 2020-09-22 2021-06-25 江南大学 一种松香基小分子有机凝胶剂及其形成的环己烷凝胶

Also Published As

Publication number Publication date
GB784001A (en) 1957-10-02
FR1134857A (fr) 1957-04-18
CH347712A (de) 1960-07-15
DE1108079B (de) 1961-05-31
BE540225A (de)
NL95407C (de)
NL199728A (de)

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