US3353984A - Method for the preparation of lightsensitive diazotype materials and improved materials prepared by such method - Google Patents

Method for the preparation of lightsensitive diazotype materials and improved materials prepared by such method Download PDF

Info

Publication number
US3353984A
US3353984A US360131A US36013164A US3353984A US 3353984 A US3353984 A US 3353984A US 360131 A US360131 A US 360131A US 36013164 A US36013164 A US 36013164A US 3353984 A US3353984 A US 3353984A
Authority
US
United States
Prior art keywords
coating
solution
dispersion
diazo
water
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
US360131A
Other languages
English (en)
Inventor
Landau Raphael
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Application granted granted Critical
Publication of US3353984A publication Critical patent/US3353984A/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
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/52—Compositions containing diazo compounds as photosensitive substances
    • G03C1/61—Compositions containing diazo compounds as photosensitive substances with non-macromolecular additives

Definitions

  • Coating solutions or dispersions usually employed in the preparation of light-sensitive diazotype materials may comprise one or more light-sensitive diazonium compounds, one or more coupling components, a dye coupling inhibitor such as an acid, anti-yellowing compounds such as thiourea and humectants such as zinc chloride.
  • a dye coupling inhibitor such as an acid
  • anti-yellowing compounds such as thiourea
  • humectants such as zinc chloride
  • a method of preparing light-sensitive diazotype materials is already known in which a base material support such as, for instance a paper base material is first coated with a pre-coating composition and is subsequently coated with a sensitizing composition such as, for instance,
  • the pre-coating composition usually comprises a substance having a colloidal structure but it has not heretofore contained the essential element of the sensitizing composition, namely the diazo constituent.
  • Another known method of preparing light-sensitive diazo type materials is to coat the base material or support with a solution which contains both the sensitizing and the pre-coating ingredients.
  • An improved method of preparing light-sensitive diazotype materials comprises coating a base material or support with two separate coating solutions or dispersions, a first solution or dispersion comprising a part or all of the diazonium compound or diazonium compounds comprising the sensitizing composition with or without a part of the other ingredients comprising said sensitizing composition, while the second solution or dispersion, which is applied to the base material or support subsequently to the application of said first solution or dispersion, contain the other ingredients comprising the sensitizing composition and the remaining part (if any) of the diazonium compound or diazonium compounds, said second solution or dispersion being so constituted as to prevent any substantial removal of the diazo from the first coating during application of said second coating.
  • the second solution or dispersion is applied to the same surface of the base material support either before or after the first coating is dried.
  • This method of procedure can be termed after-coat: ing to distinguish it from the term pre-coating where ice all the diazo compound is present in the second coating solution and it has the following advantages:
  • the method of the present invention permits the sensitization of the base material or support with sensitizing elements which it has not been possible to use heretofore as these would otherwise precipitate if included together in the same solution. This is the case with numerous diazos and couplers having excellent qualities for use in the preparation of diazotype materials but which, due to their incompatability in solution, it has not previously been possible heretofore to incorporate them in the same sensitizing solution.
  • the improved method of the present invention increases considerably and in an unexpected manner, the possible combinations of diazo and coupling components which can be employed in the preparation of lightsensitive diazotype materials.
  • the method of the present invention results in a surprising increase in sensitivity and/0r density. This is possibly due to the fact that when paper, for instance, is sensitised with a highly concentrated solution only part of the products is absorbed into the base while much is precipitated over the fibres of the paper. This precipitation is due to the high concentration of the sensitising solution augmented in part by a partial evaporation of the solvent during drying and in part by the selective solubility of the solvent in the support. The precipitated products are unable to penetrate into the interior of the fibres. It is known that precipitated diazos in a weakly or non-ionized form are less sensitive to light.
  • the method of the present invention it is possible to produce the first solution or dispersion in such a way that all the diazo is in an ionized and well dispersed form.
  • the second solution or dispersion which may be termed the overcoat may contain precipitants and is preferably such as not to wash out the diazo applied to the base by the first coating although small quantities of diazo which may be deposited. on the surface of the base fibres may be removed by washing without deleterious effects.
  • the action of the precipitant should be correspondingly vigorous. In general, the more soluble the diazo or diazos, the more vigorous should be the action of the precipitant.
  • the second coating solution should not contain substances which would dissolve any substantial amount of the diazo already deposited by the first coating.
  • the second coating solution should contain agents which reduce the solubility of the diazo, for example, substances which form sparingly soluble double salts with the diazo, such as zinc chloride, stannous chloride,
  • silicofiuorates the chlorates and sulphates of alkaline or alkaline earth metals, sulphonated or non-sulphonated couplers, soluble ferrocyanides such as alkaline metal fer-rocyanides, sulphonated benzene or naphthalene and in general any substances which diminish the solubility of the diazo without decreasing its sensitivity, may be employed.
  • the second solution substances which are easily soluble in water or in the solvent I employed. It may sometimes be useful to add small proportions of soluble substances to the first coating solution. This procedure may be useful, for instance, when soluble acids which protect the diazo against decomposition on drying are employed.
  • the second coating solution may contain diazo compounds which may be different from those used in the first coating solution. They should not, however, precipitate with the products used in the second coating which are used to insolubilise the diazo in the first coating, or used in an amount below the precipitating concentration.
  • the first and second coating solutions may contain constituents usually employed in the heretofore known precoating composition, for instance, silica or other pigments, binders such as starch, polyvinyl acetate, polyvinyl-alcohol, gelatine and other colloids.
  • constituents usually employed in the heretofore known precoating composition for instance, silica or other pigments, binders such as starch, polyvinyl acetate, polyvinyl-alcohol, gelatine and other colloids.
  • the method of the present invention has a further advantage in that prints produced from the materials prepared thereby have less tendency to bleed than when coated by known methods.
  • a further advantage of the method of this invention resides in the increase of the brightness of the dye formed due probably to the fact that the dye formed is in a more divided state on the surface.
  • the method of this invention may be applied to all processes such as the one or two-component processes for semi-dry or ammonia gas development respectively or for heat development processes or similar processes.
  • All diazos soluble in water can be used for the purpose of sensitising a support which absorbs or is swollen by water. All diazos soluble in a mixture of water and organic solvent or in an organic solvent or a mixture of organic solvents without water can be used when the supports absorb or are swollen by these solvents.
  • the diazo can also be dissolved in a colloid which is deposited on the base and in this case the colloid constitutes the carr er.
  • an improved method of preparing two component light-sensitive diazotype materials therefore, comprises coating a base material or support with a first solution or dispersion comprising 2,5 di-n-butoxy-4-morpholino benzene diazonium chloride, together with certain of the other ingredients of the sensitising composition, but not including the coupling component and then before or after the first coating is dry with a second solution or dispersion comprising 2,3-dihydroxy naphthalene together with the remaining ingredients of the sensitising composition.
  • An improved two component light-sensitive diazotype material comprises a base material or support coated with a first solution or dispersion comprising water, 2,5.di-.n-butoxy-4-morpholino benzene, diazonium chloride, citric acid, silica and polyvinyl acetate aqueous dispersion and then with a second solution or dispersion comprising water, 2,3-dihydroxy naphthalene, citric acid, zinc chloride, sodium thiocyanate, thiourea and diethyle e, glycol.
  • Coupling components soluble in water can be used in the sensitisation of supports which absorb or are swollen by water.
  • Coupling components soluble in a mixture of water and organic solvents or in a mixture of organic solvents without water can be used to sensitise supports which absorb or are swollen by these mixtures.
  • Phenols and substituted phenols e.g. p-xylenol
  • Couplers containing a reactive methylene groups 2-hydroxy naphthalene-6-sulphonic acid
  • Beta hydroxynaphthalene amides (d) Couplers containing a reactive methylene groups:
  • stabilising components can be used:
  • Organic acids such as citric acid or tartaric acid and inorganic acids such as sulphuric acid or hydrochloric acid;
  • Salts of inorganic acids such as zinc chloride and aluminium sulfate, cadmium sulphide, magnesium chloride etc.
  • the .following hygroscopic agents and development accelerators such as for example, polyglycols, glycerol, 1- allyl-3-[3-hydroxyethyl-2-thiourea may be employed.
  • a particularly useful and important feature of the present invention is that it is possible to include in the second coating solution or dispersion of a soluble thiocyanate salt and/ or zinc chloride, to act as a precipitant.
  • Paper, tracing cloth, saponified or non-saponified cellulose acetate films, films of polyethylene, polyamide, polystyrene and other plastic materials, metal foils particularly aluminium foils having a layer of aluminium hydroxide thereon can be employed.
  • EXAMPLE 1 A paper base material is coated first with the following solution:
  • a material is obtained having a dense black line with excellent stability, contrast, uniformity of background and fast to water.
  • the elements of the two baths cannot be combined into one bath without crystallisation occurring.
  • EXAMPLE 3 A paper base material is sensitised with the following two baths to obtain a material suitable for semi-dry development:
  • a material is produced having a blacker line and a sensitivity 30% greater than if the solution of Bath No. 1 were employed with three times the quantity of citric acid which is the usual sensiti-sing solution and no second bath were used. On the other hand, the addition of the elements of the second bath to the first would result in crystallisation.
  • Citric acid do .5
  • a film thus sensitised produces intermediate copies of high quality.
  • a two component light-sensitive diazotype material comprises a base material or support coated with a firstsolution or dispersion, prepared as follows:
  • the second coating solution or dispersion includes sodium thiocyanate which, as previously mentioned, has been found to be particularly satisfactory as a precipitant.
  • Alternative thiocyanates may include ammonium thiocyanate, zinc thiocyanate or indeed any other thiocyanate soluble in the solvent of the second coating solution or dispersion.
  • a method of preparing a light-sensitive diazo-type material which method comprises applying to a base material a first solution or dispersion containing a diazonium compound to form a.first coating and subsequently applying directly over the said first coating a second solution or dispersion containing a diazonium compound and a precipitant for the diazonium compound to form a second coating, the said second coating being contiguous with the first coating, said precipitant being selected from the group consisting of thiocyanates, tungstates, fluoroborates, silicofluorates, chlorides and sufates of the alkaline or alkaline earth metals, water soluble ferrocyanides and sulphonated benzene or naphthalene.
  • a method of preparing light sensitive diazotype materials according to claim 1 wherein the second coating solution or dispersion is applied either before or after the first coating solution or dispersion which has been applied to the base material is dried.
  • the second solution or dispersion includes the di-ethanolarnide of betahydroxy-naphthoic acid.
  • a method according to claim 1 wherein the first solution or dispersion is an aqueous dispersion or solution containing citric acid, silica and polyvinyl acetate.
  • the second solution or dispersion is an aqueous solution containing 2,3-dihydroxy naphthalene, citric acid, sodium thiocyanate, thiourea and diethylene glycol.

Landscapes

  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
US360131A 1963-04-18 1964-04-15 Method for the preparation of lightsensitive diazotype materials and improved materials prepared by such method Expired - Lifetime US3353984A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB1526963 1963-04-18
GB2083463 1963-05-24

Publications (1)

Publication Number Publication Date
US3353984A true US3353984A (en) 1967-11-21

Family

ID=26251169

Family Applications (1)

Application Number Title Priority Date Filing Date
US360131A Expired - Lifetime US3353984A (en) 1963-04-18 1964-04-15 Method for the preparation of lightsensitive diazotype materials and improved materials prepared by such method

Country Status (3)

Country Link
US (1) US3353984A (en)van)
CH (1) CH441999A (en)van)
SE (1) SE335474B (en)van)

Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3484241A (en) * 1967-01-16 1969-12-16 Ibm Diazo type films with extended linear latitude
US3607287A (en) * 1968-12-30 1971-09-21 Keuffel & Esser Co Negative-working two-component diazosulfonate material
US3622325A (en) * 1968-03-07 1971-11-23 Ricoh Kk Diazotype photographic copying material adapted for wet development and for producing copied image in black color
US3628954A (en) * 1970-03-24 1971-12-21 Keuffel And Esser Co Diazo material and visible light development process therefore
US3642483A (en) * 1966-11-07 1972-02-15 Ricoh Kk Thermally developable diazotype copying materials
US3650750A (en) * 1968-12-28 1972-03-21 Ricoh Kk Heat-developable diazo-type light-sensitive material
US3836366A (en) * 1972-09-11 1974-09-17 Lith Kem Corp Planographic printing plates and method for their preparation
US3837858A (en) * 1972-09-11 1974-09-24 Lith Kem Corp Printing plate and method of making the same
US3899332A (en) * 1972-09-11 1975-08-12 Lith Kem Corp Printing plate and method of making the same
US3904414A (en) * 1971-09-24 1975-09-09 Gaf Corp Precoated diazotype photocopying materials
US3912512A (en) * 1974-03-04 1975-10-14 Addressograph Multigraph Light-sensitive diazotype film and method of making and using same
US3918974A (en) * 1970-05-01 1975-11-11 Mita Industrial Co Ltd Process for the diazo-type multicolor reproduction
US3930856A (en) * 1972-08-02 1976-01-06 Ozalid Company Limited Photopolymerisable compositions and their uses with diazonium salts as photocatalysts
US3976488A (en) * 1969-02-19 1976-08-24 Mita Industrial Company, Ltd. Treating agent for diazo-type multicolor reproduction
US4093465A (en) * 1973-08-14 1978-06-06 Polychrome Corporation Photosensitive diazo condensate compositions
US4195998A (en) * 1974-04-15 1980-04-01 Eastman Kodak Company CO(III) Complex containing radiation sensitive element with diazo recording layer
US4201588A (en) * 1974-04-15 1980-05-06 Eastman Kodak Company Radiation sensitive co(III)complex photoreduction element with image recording layer
US4230492A (en) * 1978-01-17 1980-10-28 The Richardson Company Aryl sulfonic acid based stabilizers for presensitized planographic plates
US4263392A (en) * 1979-06-01 1981-04-21 Richardson Graphics Company Ultra high speed presensitized lithographic plates
US4314019A (en) * 1976-09-07 1982-02-02 Eastman Kodak Company Transition metal photoreduction systems and processes
US4334003A (en) * 1979-06-01 1982-06-08 Richardson Graphics Company Ultra high speed presensitized lithographic plates
US4452876A (en) * 1979-11-28 1984-06-05 Andre Schaeffer Steam, water or heat developing diazotype material
US4467024A (en) * 1981-12-08 1984-08-21 Ricoh Co., Ltd. Process for the production of thermo-developable type diazo copying material
US4495269A (en) * 1982-09-22 1985-01-22 Am International, Inc. Waterborne two component diazo type coating composition with hydrolyzed polyvinyl acetate and hexamethoxy methylmelamine resin
US4499170A (en) * 1983-06-17 1985-02-12 Richardson Graphics Company Lithographic plates and photoresists having stabilized photosensitive diazo resin with theophylline derivative
US4511642A (en) * 1982-02-17 1985-04-16 Nippon Telegraph And Telephone Public Corp. Photo-fixing heat-sensitive recording media with photosensitive diazonium salt, coupler, and organic boron salt
US4568628A (en) * 1982-09-21 1986-02-04 Polychrome Corporation Water developable diazo printing plate composition with quaternary nitrogen stabilizer
US4576899A (en) * 1984-05-01 1986-03-18 Imperial Metal & Chemical Company Method for enhancing apparent photospeed of diazonium plates by using thiocyanate to insolubilize diazonium compound after photolysis
EP0122523A3 (en) * 1983-04-18 1987-05-27 Andrews Paper and Chemical Co., Inc. Diazotype compositions and materials
US4842982A (en) * 1984-09-11 1989-06-27 Hoechst Aktiengesellschaft Radiation-sensitive recording material having radiation-sensitive recording layer and discontinuous radiation-sensitive covering layer of the same composition
US4863827A (en) * 1986-10-20 1989-09-05 American Hoechst Corporation Postive working multi-level photoresist
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
US5223376A (en) * 1986-06-20 1993-06-29 Toyo Soda Manufacturing Co., Ltd. Method for producing fine patterns utilizing specific polymeric diazonium salt, or diazonium salt/sulfone group containing polymer, as photobleachable agent

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB571802A (en) * 1944-01-07 1945-09-10 Hall Harding Ltd Improvements in or relating to photographic diazotype printing processes
US2616803A (en) * 1948-03-11 1952-11-04 Leonard E Ravich Diazotype dyeing and printing of web or sheet material
US2617726A (en) * 1947-07-10 1952-11-11 Grinten Chem L V D Light-sensitive diazotype materials
US2659672A (en) * 1948-01-09 1953-11-17 Hall Harding Ltd Diazotype photoprinting materials
US2793118A (en) * 1952-08-13 1957-05-21 Grinten Chem L V D One component diazotype material containing at least two light sensitive diazocompounds
GB864011A (en) * 1957-03-16 1961-03-29 Raphael Landau Diazo type printing material and a method of making diazo type prints
US3028240A (en) * 1958-01-18 1962-04-03 Keuffel & Esser Co Light sensitive diazotype materials
US3046128A (en) * 1958-07-03 1962-07-24 Dietzgen Co Eugene Thermally developable diazotype photoprinting material and production thereof
US3061397A (en) * 1957-06-14 1962-10-30 Gen Aniline & Film Corp Metallizing azoic dyeings
US3102812A (en) * 1960-11-16 1963-09-03 Gen Aniline & Film Corp Stabilizers for one-component diazotype materials
US3113023A (en) * 1961-07-25 1963-12-03 Polychrome Corp Photosensitive lithographic plate comprising photosensitive diazo resins and method for preparing same

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB571802A (en) * 1944-01-07 1945-09-10 Hall Harding Ltd Improvements in or relating to photographic diazotype printing processes
US2617726A (en) * 1947-07-10 1952-11-11 Grinten Chem L V D Light-sensitive diazotype materials
US2659672A (en) * 1948-01-09 1953-11-17 Hall Harding Ltd Diazotype photoprinting materials
US2616803A (en) * 1948-03-11 1952-11-04 Leonard E Ravich Diazotype dyeing and printing of web or sheet material
US2793118A (en) * 1952-08-13 1957-05-21 Grinten Chem L V D One component diazotype material containing at least two light sensitive diazocompounds
GB864011A (en) * 1957-03-16 1961-03-29 Raphael Landau Diazo type printing material and a method of making diazo type prints
US3061397A (en) * 1957-06-14 1962-10-30 Gen Aniline & Film Corp Metallizing azoic dyeings
US3028240A (en) * 1958-01-18 1962-04-03 Keuffel & Esser Co Light sensitive diazotype materials
US3046128A (en) * 1958-07-03 1962-07-24 Dietzgen Co Eugene Thermally developable diazotype photoprinting material and production thereof
US3102812A (en) * 1960-11-16 1963-09-03 Gen Aniline & Film Corp Stabilizers for one-component diazotype materials
US3113023A (en) * 1961-07-25 1963-12-03 Polychrome Corp Photosensitive lithographic plate comprising photosensitive diazo resins and method for preparing same

Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3642483A (en) * 1966-11-07 1972-02-15 Ricoh Kk Thermally developable diazotype copying materials
US3484241A (en) * 1967-01-16 1969-12-16 Ibm Diazo type films with extended linear latitude
US3622325A (en) * 1968-03-07 1971-11-23 Ricoh Kk Diazotype photographic copying material adapted for wet development and for producing copied image in black color
US3650750A (en) * 1968-12-28 1972-03-21 Ricoh Kk Heat-developable diazo-type light-sensitive material
US3607287A (en) * 1968-12-30 1971-09-21 Keuffel & Esser Co Negative-working two-component diazosulfonate material
US3976488A (en) * 1969-02-19 1976-08-24 Mita Industrial Company, Ltd. Treating agent for diazo-type multicolor reproduction
US3628954A (en) * 1970-03-24 1971-12-21 Keuffel And Esser Co Diazo material and visible light development process therefore
US3918974A (en) * 1970-05-01 1975-11-11 Mita Industrial Co Ltd Process for the diazo-type multicolor reproduction
US3904414A (en) * 1971-09-24 1975-09-09 Gaf Corp Precoated diazotype photocopying materials
US3930856A (en) * 1972-08-02 1976-01-06 Ozalid Company Limited Photopolymerisable compositions and their uses with diazonium salts as photocatalysts
US3899332A (en) * 1972-09-11 1975-08-12 Lith Kem Corp Printing plate and method of making the same
US3837858A (en) * 1972-09-11 1974-09-24 Lith Kem Corp Printing plate and method of making the same
US3836366A (en) * 1972-09-11 1974-09-17 Lith Kem Corp Planographic printing plates and method for their preparation
US4093465A (en) * 1973-08-14 1978-06-06 Polychrome Corporation Photosensitive diazo condensate compositions
US3912512A (en) * 1974-03-04 1975-10-14 Addressograph Multigraph Light-sensitive diazotype film and method of making and using same
US4201588A (en) * 1974-04-15 1980-05-06 Eastman Kodak Company Radiation sensitive co(III)complex photoreduction element with image recording layer
US4195998A (en) * 1974-04-15 1980-04-01 Eastman Kodak Company CO(III) Complex containing radiation sensitive element with diazo recording layer
US4314019A (en) * 1976-09-07 1982-02-02 Eastman Kodak Company Transition metal photoreduction systems and processes
US4230492A (en) * 1978-01-17 1980-10-28 The Richardson Company Aryl sulfonic acid based stabilizers for presensitized planographic plates
US4263392A (en) * 1979-06-01 1981-04-21 Richardson Graphics Company Ultra high speed presensitized lithographic plates
US4334003A (en) * 1979-06-01 1982-06-08 Richardson Graphics Company Ultra high speed presensitized lithographic plates
US4452876A (en) * 1979-11-28 1984-06-05 Andre Schaeffer Steam, water or heat developing diazotype material
US4467024A (en) * 1981-12-08 1984-08-21 Ricoh Co., Ltd. Process for the production of thermo-developable type diazo copying material
US4511642A (en) * 1982-02-17 1985-04-16 Nippon Telegraph And Telephone Public Corp. Photo-fixing heat-sensitive recording media with photosensitive diazonium salt, coupler, and organic boron salt
US4568628A (en) * 1982-09-21 1986-02-04 Polychrome Corporation Water developable diazo printing plate composition with quaternary nitrogen stabilizer
US4495269A (en) * 1982-09-22 1985-01-22 Am International, Inc. Waterborne two component diazo type coating composition with hydrolyzed polyvinyl acetate and hexamethoxy methylmelamine resin
EP0122523A3 (en) * 1983-04-18 1987-05-27 Andrews Paper and Chemical Co., Inc. Diazotype compositions and materials
US4499170A (en) * 1983-06-17 1985-02-12 Richardson Graphics Company Lithographic plates and photoresists having stabilized photosensitive diazo resin with theophylline derivative
US4576899A (en) * 1984-05-01 1986-03-18 Imperial Metal & Chemical Company Method for enhancing apparent photospeed of diazonium plates by using thiocyanate to insolubilize diazonium compound after photolysis
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
US4842982A (en) * 1984-09-11 1989-06-27 Hoechst Aktiengesellschaft Radiation-sensitive recording material having radiation-sensitive recording layer and discontinuous radiation-sensitive covering layer of the same composition
US5223376A (en) * 1986-06-20 1993-06-29 Toyo Soda Manufacturing Co., Ltd. Method for producing fine patterns utilizing specific polymeric diazonium salt, or diazonium salt/sulfone group containing polymer, as photobleachable agent
US4863827A (en) * 1986-10-20 1989-09-05 American Hoechst Corporation Postive working multi-level photoresist

Also Published As

Publication number Publication date
SE335474B (en)van) 1971-05-24
CH441999A (de) 1967-08-15

Similar Documents

Publication Publication Date Title
US3353984A (en) Method for the preparation of lightsensitive diazotype materials and improved materials prepared by such method
US3255011A (en) Two-component diazotype photoprinting material susceptible to thermal development
US2727820A (en) Light-sensitive diazotype layers containing carboxamides
US2871119A (en) Diazotype reproduction material and method
US2822272A (en) Light sensitive diazotype material
US2854338A (en) Negative working diazo sulfonate foils
US2537098A (en) Sulfonamide azo coupling components used in diazo types
US3365296A (en) Light-sensitive ultraviolet absorbing compounds and diazotype materials containing the same
US2717832A (en) Diazotype materials for black line images containing diresorcyl sulfide or sulfoxide as a subsitiute for resorcinol
US2474700A (en) Diazotype sensitized papers having cellulose ether sizing
US2616803A (en) Diazotype dyeing and printing of web or sheet material
US2792303A (en) Process for the production of diazotype copies
GB687751A (en) Process and material for the direct production of positive photographic images
US2772974A (en) Light sensitive diazotype materials
US2773768A (en) Light-sensitive diazotype material
US2487446A (en) Process for preventing stains on photographic color material during drying following exposure, bleaching, and fixing treatment
US2710256A (en) Photographic print-out process
US2661291A (en) Antidiffusion diazotypes having tetrazo diphenyls as the light sensitive agent
US2542716A (en) Multicolor diazotype layers
US3622326A (en) Diazotype light-sensitive copying papers intended for wet development and for use in the preparation of intermediates
US3164469A (en) One-component diazo process
US2756144A (en) Photochemical multicolor printing of textile and the like
US2591309A (en) Photographically sensitive diazotype element
US2632703A (en) Light sensitive diazotype materials containing tetrazo diphenyl compounds
US3367776A (en) Heat sensitive diazotype materials