US3046131A - Photographic material containing light sensitive quinone diazides - Google Patents

Photographic material containing light sensitive quinone diazides Download PDF

Info

Publication number
US3046131A
US3046131A US71518258A US3046131A US 3046131 A US3046131 A US 3046131A US 71518258 A US71518258 A US 71518258A US 3046131 A US3046131 A US 3046131A
Authority
US
United States
Prior art keywords
water
layer
water soluble
soluble salt
acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
Other languages
English (en)
Inventor
Schmidt Maximilian Paul
Rebenstock August
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Azoplate Corp
Original Assignee
Azoplate Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Azoplate Corp filed Critical Azoplate Corp
Application granted granted Critical
Publication of US3046131A publication Critical patent/US3046131A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/092—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by backside coating or layers, by lubricating-slip layers or means, by oxygen barrier layers or by stripping-release layers or means
    • 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
    • G03F7/0226—Quinonediazides characterised by the non-macromolecular additives
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/162—Protective or antiabrasion layer
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31844—Of natural gum, rosin, natural oil or lac

Definitions

  • This invention relates to an improved light-sensitive material which is especially useful in the field of reproduction. More particularly it relates to laminated material comprising a support layer an intermediate layer containing a light-sensitive and water-insoluble substance and a coating of a water-soluble substance.
  • Water-insoluble diazo compounds belonging to the group of the so-called diazo anhydrides otherwise known as quinone diazides have been found to be well suited for sensitizing a base material for making images which can be used as stencils or after inking with greasy printing ink, as printing plates.
  • the water-insoluble diazo compounds, in solution with organic solvents are coated in a thin layer on a support layer, preferably on metal foils or plates. After the layers have been dried and exposed to light under a pattern the exopsed material can be developed with dilute kaline solutions to show a positive image from a positive master and a negative image from a negative master, or when certain of the water-insoluble diazo anhydrides are used, development may be accomplished with dilute acids. Development with acid reacting agents provides positive images from negative masters and negative images from positive masters.
  • the lightsensitive layers for example such layers as have been produced from water-insoluble quinone diazides, often show a feeble coloring in those areas of the layer that are not covered by the pattern and that contact the glass of the copying frame.
  • This coloring may be caused by heat radiation from the glass but whatever its cause it is disadvantageous in that it is very ditficult to remove and may cause a coloring of the background of the copies drawn from the image.
  • the protective coating may be produced by applying to the surface of the light-sensitive layer by means of, for example, a brush or a plate-whirler, an aqueous solution of dextrine, gum arabic, mesquite gum, tragacanth, water-soluble salts of pectic acid and alginic acid, water-soluble cellulose others, such as methylcellulose, hydroxyethylcellulose, water-soluble salts of carboxyalkyl cellulose, water soluble salts of carboxy alkyl starch, glue, albumen, pepton, water-soluble caseinates, polyvinyl alcohol, polyvinylpyrolidone, polyacrylamides, water-soluble salts of polyacrylic acids or other water-soluble polymerization products, which are capable of forming films. After drying the solution which has been applied covers the lightsensitive layer as a protective coating.
  • aqueous solutions containing 0.2 to of the colloidal substances and showing an approximately neutral re ction are suited for producing the colloidal coating.
  • the presence of the protective coating prevents the direct contact between the light-sensitive layer and the glass of the copying apparatus.
  • Another important advantage of the coating is that it protects the thin light-sensitive diazo layer from being damaged by friction, dust or direct contact with the fingers. If the light-sensitive layer is not protected and is touched by the man handling it, then fingerprints become reproduced on the copies during the printing and especially in the cases where the negative working process is followed.
  • the coating also improves development of the image because it provides for improved wetting of the exposed layer.
  • wetting or emulsifying agents such as alkyl substituted naphthalene sulfonic acids, saponins or sulfonates of high molecular aliphatic alcohols to the solutions of watersoluble film forming substances improves the formation of a uniform coating and the development of the images.
  • a 1.5% solution of the a-naphthylester of naphthoquinone-( 1,2)-diazide-( 2)-5-sulfonic acid in glycol-mono methylether is coated as for example, with the use of rollers as a thin layer on an aluminum foil which has been mechanically roughened. After drying the layer, a 4 to 6% aqueous solution of gum arabic or dextrine is applied to the layered foil in the same manner and then dried.
  • the material thus obtained is exposed to light under a master and subsequently developed with a 3% aqueous solution of trisodium phosphate. From a positive master a positive image is obtained. A perfectly clean background is obtained in those areas which had not been protected by the master and which contacted the glass.
  • esters or amides of a quinone diazide sulfonic acid may be used for the formation of the light-sensitive layer underneath the water-soluble layer.
  • the u-naphthylester of naphthoquinone-(1,2)-diazzide-(2)-5-sulfonic acid is produced in the following manner:
  • a 1% solution of the naphthoquinone-(l,2)-diazide- (2)-4-sulfonic acid ester of 7-hydroxy-2-e'thyl-N-(n-propyl)naphth'o-1,2:4,5-imidazole in glycolmonomethylether is whirl-coated onto a roughened or superficially oxidized aluminum foil.
  • a 5% aqueous solution of dextrine or a 1% aqueous solution of polyvinyl-alcohol mixed with a small quantity of a saponin is coated onto the dried layer by means of a cotton swab and dried.
  • the light-sensitive material thus obtained is exposed to light under a transparent negative; then the exposed layer is developed by wiping over with a 2.5% phosphoric acid with the aid of a cotton swab and the developer is removed by rinsing the layer with water. After rubbing in with greasy printing ink the thus obtained positive image may be used for printing in the usual manner.
  • the reaction mixture is dissolved in water and by neutralizing the aqueous solution with the aid of hydrochloric acid the crude 7-hydroxy 2 ethyl 1(or 3) N (n propyl) naphtho 1,2:4,5-imidazole is separated out.
  • the imidazole is purified by recrystallization from alcohol and then has a melting point of 250 to 251 C.
  • the exposed layer After exposing the dried layer under a positive pattern, the exposed layer is developed with a 3% aqueous solution of trisodium-phosphate and then rinsed with water.
  • the positive image thus obtained can be used, in the usual way, for printing in a customary offset printing machine. This process guarantees prints free from tone, whereas plates not coated with alginate show some tone wherever they come into contact with the glass plate of the copying machine.
  • condensation product of 2 moles of naphthoquinone-(1,2)-diazide-(2)-5-sulfochloride and 1 mole of 2,2'-dihydroxy-l,l'-dinaphthylmethane can be prepared in a manner similar to that described in Example 1 and the product corresponds to the following structural formula:
  • V o ll ll may, @Nz
  • a mechanically roughened alu- -rninum foil is coated with a solution containing 2% naphthoquinone-( 1,2 -diaZide-( 2 -5 -sulfonic acid-p-xylide and 0.2% 1phenyl-3-methylpyrazolon-5, dissolved in glycolmonornethylether.
  • the coated side of the foil is exposed to light under a positive pattern.
  • the exposed oil is r t s e e t9 he i fl en a mo ia gas whereby a positive image of the pattern appears.
  • the background of the image is cleared by treating the coated side of the toil with a solution of 5% aqueous disodium-phosphate.
  • the toll is then rinsed with water.
  • the image side of the foil is briefly treated with a solution of gum arabic in phosphoric acid (10 g. phosphoric acid and g. gum arabic to one liter of water).
  • the foil can then be used for printing in the offset machine. Prints which are free from tone are obtained, in contrast to foils prepared without any sodium polyacrylate coating which are strongly toning wherever, during the printing process, they have come into direct contact with the glass of the copying machine.
  • the above mentioned p-xylidide can be produced in I the usual way by causing naphthoquinone-(1,2)diazide- (2)-5-sulfonic acid to react with xylidine in an organic solvent in the presence of acid binding substances.
  • Laminated material for use in photography consisting of a support layer, an intermediate layer of light sensitive material comprising a water insoluble quinone diazide, and a top coat consisting essentially of a substance of the group consisting of dextrine, gum arabic, mesquite gum, water-soluble salt of the group consisting of pectic acid and alginic acid, water soluble cellulose ether, water soluble salt of carboxy alkyl cellulose, water soluble salt of carboxy alkyl starch, glue, albumen, pepton, water soluble, caseinate, polyvinylalcohol, polyvinylpyrolidone, polyacrylamide, and water soluble salt of poly-acrylic acid.
  • Laminated material for use in photography consisting of a support layer, an intermediate layer comprising a water insoluble quinone diazide, and a top coat consisting essentially of dextrin.
  • Laminated material for use in photography consisting of a support layer, an intermediate layer comprising a water insoluble quinone diazide, and a top coat consisting essentially of polyvinyl alcohol.
  • Laminated material for use in photography consisting of a support layer, an intermediate layer comprising a water insoluble quinone diazide, and a top coat consisting essentially of gum arabic.
  • Laminated material for use in photography consisting of a support layer, an intermediate layer comprising a water insoluble quinone diazide, and a top coat consisting essentially of alginic acid.
  • Laminated material for use in photography consisting of a support layer, an intermediate layer comprising a water insoluble quinone diazide, and a top coat consisting essentially of a water soluble salt of carboxyl alkyl cellulose.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Architecture (AREA)
  • Structural Engineering (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Printing Plates And Materials Therefor (AREA)
US71518258 1952-01-05 1958-02-14 Photographic material containing light sensitive quinone diazides Expired - Lifetime US3046131A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEK12749A DE918848C (de) 1952-01-05 1952-01-05 Unter Verwendung von Diazoverbindungen hergestelltes lichtempfindliches Material

Publications (1)

Publication Number Publication Date
US3046131A true US3046131A (en) 1962-07-24

Family

ID=25793124

Family Applications (1)

Application Number Title Priority Date Filing Date
US71518258 Expired - Lifetime US3046131A (en) 1952-01-05 1958-02-14 Photographic material containing light sensitive quinone diazides

Country Status (7)

Country Link
US (1) US3046131A (en))
BE (1) BE516716A (en))
CH (1) CH311827A (en))
DE (1) DE918848C (en))
FR (1) FR1069408A (en))
GB (1) GB735129A (en))
NL (1) NL77599C (en))

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3868254A (en) * 1972-11-29 1975-02-25 Gaf Corp Positive working quinone diazide lithographic plate compositions and articles having non-ionic surfactants
US4093463A (en) * 1977-02-22 1978-06-06 Eastman Kodak Company Water soluble binder overcoat on vesicular element containing N2 -releasing agent
US4168979A (en) * 1974-03-19 1979-09-25 Fuji Photo Film Co., Ltd. Light-sensitive printing plate with matt overlayer
US4197128A (en) * 1973-05-29 1980-04-08 Fuji Photo Film Co., Ltd. Light-sensitive O-quinone diazide containing copying material
US4200463A (en) * 1975-12-19 1980-04-29 Motorola, Inc. Semiconductor device manufacture using photoresist protective coating
US4268611A (en) * 1974-03-19 1981-05-19 Fuji Photo Film Co., Ltd. Contact photographic process for producing a planographic printing plate
US4292392A (en) * 1976-02-25 1981-09-29 Fuji Photo Film Co., Ltd. Protective layer of fatty acid or nylon on photosensitive resin for metal-image forming element
WO1986007473A1 (en) * 1985-06-03 1986-12-18 Fairmount Chemical Co., Inc. Contrast enhancement layer
US4784936A (en) * 1985-10-24 1988-11-15 General Electric Company Process of forming a resist structure on substrate having topographical features using positive photoresist layer and poly(vinyl pyrrolidone) overlayer
US5188924A (en) * 1984-05-14 1993-02-23 Kabushiki Kaisha Toshiba Pattern forming method utilizing material with photoresist film underlayer and contrast enhancement overlayer containing photosensitive diazonium salt

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL77599C (en)) * 1952-01-05 1954-10-15
US3046114A (en) * 1955-03-01 1962-07-24 Azoplate Corp Diazo compounds and printing plates manufactured therefrom
DE4040117C2 (de) * 1990-12-13 1994-02-17 Fotochem Werke Gmbh Stahlenempfindliches Material für die Elektronenstrahl- und Röntgenstrahllithographie und Verfahren zur Trockenentwicklung des Materials
US5506090A (en) * 1994-09-23 1996-04-09 Minnesota Mining And Manufacturing Company Process for making shoot and run printing plates

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE497135A (en)) * 1949-07-23
BE516716A (en)) * 1952-01-05 1900-01-01
US2667415A (en) * 1948-10-15 1954-01-26 Azoplate Corp Process for producing positive photolithographic printing foils
US2702243A (en) * 1950-06-17 1955-02-15 Azoplate Corp Light-sensitive photographic element and process of producing printing plates

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2667415A (en) * 1948-10-15 1954-01-26 Azoplate Corp Process for producing positive photolithographic printing foils
BE497135A (en)) * 1949-07-23
US2702243A (en) * 1950-06-17 1955-02-15 Azoplate Corp Light-sensitive photographic element and process of producing printing plates
BE516716A (en)) * 1952-01-05 1900-01-01

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3868254A (en) * 1972-11-29 1975-02-25 Gaf Corp Positive working quinone diazide lithographic plate compositions and articles having non-ionic surfactants
US4197128A (en) * 1973-05-29 1980-04-08 Fuji Photo Film Co., Ltd. Light-sensitive O-quinone diazide containing copying material
US4217407A (en) * 1973-05-29 1980-08-12 Fuji Photo Film Co., Ltd. Light-sensitive O-quinone diazide containing copying material
US4207106A (en) * 1973-05-29 1980-06-10 Fuji Photo Film Co., Ltd. Positive working O-quinone diazide photocopying process with organic resin overlayer
US4168979A (en) * 1974-03-19 1979-09-25 Fuji Photo Film Co., Ltd. Light-sensitive printing plate with matt overlayer
US4268611A (en) * 1974-03-19 1981-05-19 Fuji Photo Film Co., Ltd. Contact photographic process for producing a planographic printing plate
US4200463A (en) * 1975-12-19 1980-04-29 Motorola, Inc. Semiconductor device manufacture using photoresist protective coating
US4292392A (en) * 1976-02-25 1981-09-29 Fuji Photo Film Co., Ltd. Protective layer of fatty acid or nylon on photosensitive resin for metal-image forming element
FR2381339A1 (fr) * 1977-02-22 1978-09-15 Eastman Kodak Co Produit photographique formateur d'image vesiculaire
US4093463A (en) * 1977-02-22 1978-06-06 Eastman Kodak Company Water soluble binder overcoat on vesicular element containing N2 -releasing agent
US5188924A (en) * 1984-05-14 1993-02-23 Kabushiki Kaisha Toshiba Pattern forming method utilizing material with photoresist film underlayer and contrast enhancement overlayer containing photosensitive diazonium salt
WO1986007473A1 (en) * 1985-06-03 1986-12-18 Fairmount Chemical Co., Inc. Contrast enhancement layer
US4784936A (en) * 1985-10-24 1988-11-15 General Electric Company Process of forming a resist structure on substrate having topographical features using positive photoresist layer and poly(vinyl pyrrolidone) overlayer

Also Published As

Publication number Publication date
FR1069408A (fr) 1954-07-07
GB735129A (en) 1955-08-17
BE516716A (en)) 1900-01-01
NL77599C (en)) 1954-10-15
DE918848C (de) 1954-10-07
CH311827A (de) 1955-12-15

Similar Documents

Publication Publication Date Title
US3046116A (en) Light sensitive material for printing and process for making printing plates
US3046131A (en) Photographic material containing light sensitive quinone diazides
US2702243A (en) Light-sensitive photographic element and process of producing printing plates
US3180733A (en) Naphthoquinone diazide lithographic material and process of making printing plates therewith
US2852379A (en) Azide resin photolithographic composition
US3046120A (en) Light-sensitive layers for photomechanical reproduction
US3438778A (en) Planographic printing plate
US3046119A (en) Light sensitive material for printing and process for making printing plates
US2692826A (en) Lithographic plates
US2766118A (en) Light-sensitive material for the photomechanical reproduction and process for the production of images
US3146104A (en) Silver halide sensitized lithographic printing plate
US3640992A (en) Naphthoquinone diazide sulfonic acid ester
US3984250A (en) Light-sensitive diazoketone and azide compositions and photographic elements
US2754209A (en) Light-sensitive para quinone diazides for making printing plates
US3061429A (en) Diazo printing plates and method for the production thereof
US2772160A (en) Light-detached resists or reliefs for printing plates
US3230087A (en) Light-sensitive polymeric diazonium and azidoacrylamido reproduction materials and process for making plates therefrom
US3061435A (en) Lithographic printing plates and azido compositions therefor
US2729562A (en) Process for producing images
US3099209A (en) Process of treating residual positive silver halide images with organic sulfur to render said images oleophilic
US3046114A (en) Diazo compounds and printing plates manufactured therefrom
US2975053A (en) Reproduction material
US3634086A (en) Solvent development of light-sensitive diazo layers
US1762033A (en) Process of preparing pictures to be produced by tanning action
US2994609A (en) Development of diazotype printing plates