US3607271A - Phloroglucinol developer for lingt-sensitive planographic plates - Google Patents

Phloroglucinol developer for lingt-sensitive planographic plates Download PDF

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Publication number
US3607271A
US3607271A US790175A US3607271DA US3607271A US 3607271 A US3607271 A US 3607271A US 790175 A US790175 A US 790175A US 3607271D A US3607271D A US 3607271DA US 3607271 A US3607271 A US 3607271A
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United States
Prior art keywords
salt
solution
developer
water
percent
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Expired - Lifetime
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US790175A
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English (en)
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Aloysius Henricus Jac Hilhorst
Paul Joseph Hubert Tummers
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Van der Grinten NV
Canon Production Printing Holding BV
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Oce Van der Grinten NV
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    • 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
    • G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
    • G03C5/18—Diazo-type processes, e.g. thermal development, or agents therefor
    • 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
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/30—Imagewise removal using liquid means
    • G03F7/32—Liquid compositions therefor, e.g. developers

Definitions

  • Eslinger and Alvin Sinderbrand ABSTRACT Planographic printing plates sensitized with a benzene diazonium salt are converted into offset printing forms by imagewise exposure and subsequent development with an aqueous phloroglucinol solution buffered to a pH between 4 and 8 and containing l-lO percent by volume of water-miscible organic solvent having a molecular weight greater than 50.
  • the organic solvent avoids or greatly reduces a problem of initial prints being blemished by ink held on blank (background) areas of the printing forms.
  • Especially effective solvents such as propyl glycol, acetonyl acetone, diacetone alcohol, and N-methylpyrrolidone-2, having boiling points above 90C.
  • a high salt content in the developing solution inhibits any bleeding of the azo-dyestuff during development.
  • PHLOROGLUCINOLY DEVELOPER FOR LIGHT-SENSITIVE PLANOGRAPP'IIC PLATES This invention relates to a developing process and a developing composition for the production of printing forms having oleophilic azo-dyestufi images thereon by the treatment of light-sensitive planographic plates after image-wise exposure of planographic surfaces thereof sensitized with a light-sensitive benzene diazonium compound.
  • British Pat. specification Nos. 1,038,279 and 1,082,889 describe a process for the production of printing forms in which a paper planographic plate sensitized with an activecoupling benzene diazonium salt is imagewise exposed and subsequently developed by means of an aqueous, buffered phloroglucinol solution having a slightly acid or neutral reaction. From a printing form thus obtained some hundreds of prints can be produced.
  • British Pat. Specification No. 1,064,128 describes a similar process in which a photographic barayta paper sensitized with a light-sensitive benzene diazonium slat is image-wise exposed and subsequently developed by means of an aqueous, buffered alkaline phloroglucinol solution.
  • alkaline phloroglucinol developers is, however, not desirable, because in solutions having a pH greater than 8.5 phloroglucinol has little resistance to deterioration caused by the oxygen prevailing in the air.
  • German Pat. Specification No. 857,888 a process is described in which an anodically oxidized aluminum plate sensitized with a relatively slow-coupling benzene diazonium salt if imagewise exposed and subsequently developed by means of a solution of an azo-coupling component which preferably is a p'olyvalent aromatic hydroxyl compound, such as 2,4,2,4 tetrahydroxyldiphenyl.
  • an azo-coupling component which preferably is a p'olyvalent aromatic hydroxyl compound, such as 2,4,2,4 tetrahydroxyldiphenyl.
  • Printing forms can be produced in a simple and inexpensive way according to the processes described in said British Pat.
  • the processes are preferably carried out by applying a weakly acid to neutral buffered phloroglucinol solution to a light-sensitive planographic plate on which an active-coupling diazo compound is present.
  • the planographic plate to be sensitized can be an aluminum or a plastic foil having a planographic surface, or a so-called paper planographic printing plate.
  • This phenomenon of initial toning occurs especially when the development of the planographic printing forms is effected in a cold and dry atmosphere.
  • the initial toning is particularly annoying if only a small number of prints (50-200) are made from the printing form, for the first 20 or 30 prints are often unusable.
  • Another difficulty often encountered in the above-mentioned processes is that the azo-dyestuff image shows poor adherence to the planographic layer and, moreover, takes up the printing ink in sufficiently at the start of printing.
  • any of various organic solvents of that nature can be used effectively according to the invention.
  • suitable solvents are: aliphatic monovalent alcohols having at least three carbon atoms in the molecule, such as n-propanol; isopropanol or tertiary butanol; ethylene glycol monoalkyl ethers, such as methyl glycol or n-propylglycoli di or triethylene glycol monoand dialkyl ethers, such as diethylene glycol monomethyl-, monoethyl-, mono-n-propyl or mono-m butylethe'r, diethylene glycol dimethylor diethyl ether oi triethylene glycol dimethyl ether; esters of ethylene glycol diethylene glycoland triethylene glycol monoalkyl enters, such as methyl glycol formate, inetliyl glycol acetate, ethyl glycol acetate, diethylene glycol monomethyl ether forma'te or diethylene glycol monomethyl ether
  • a nontoxic, inodorous solvent is chosen which at room temperature has a rate of evaporation approximately equaling that of water.
  • the advantage of using such a solvent is in that the ratio between water and solvent does not chahge when the developer is stored in open vessels, for instance in ari open bottle or in the trough of a thin layer developing ap-' paratus such as widely used in the diazo-type process.
  • solvents having a boiling point above C. are preferably chosen; and n-propyl glycol, acetoriyl acetone,
  • an organic solvent according to the invention has not only the advantage that the initial toning is coun teracted but also that a better adherence of the image and good spreading of the developer over the planographic plates to be developed are obtained. Ergo, it is not necessary to add a wetting agent to the developer.
  • the developer is buffered at a pH between 4 and 8 and preferably between 6 and 7.5.
  • the developer can contain as buffer salts the salts commonly used for buffering neutral to weakly acid phloroglucinol developers, such as ammonium, alkali metal or alkaline earth metal salts of weak acids such as phosphoric acid, acetic acid, adipic acid, maleic acid, tartaric acid and citric acid.
  • the phloroglucinol solution in order to prevent any bleeding of the azodyestuff during its development, is made to contain, in addition to the buffer salt, l-10 percent by weight of a water-soluble inorganic salt derived from a strong acid, such as sodium chloride, sodium bromide, sodium iodide, sodium sulfate, sodium nitrate, potassium chloride, potassium bromide, potassium iodide, potassium nitrate, potassium sulfate, ammonium bromide, ammonium nitrate, ammonium sulfate, lithium sulfate, calcium chloride, magnesium chloride, magnesium nitrate, magnesium sulfate or aluminum sulfate,
  • a strong acid such as sodium chloride, sodium bromide, sodium iodide, sodium sulfate, sodium nitrate, potassium chloride, potassium bromide, potassium iodide, potassium nitrate, potassium sulfate, ammonium bromid
  • the salt and the quantity thereof to be added to the developer must be selected in such away that no precipitates are formed in the developer. It is evident for instance, that no calcium, aluminum or magnesium salt should be added to a developer containing a phosphate as buffer salt.
  • the developer can contain other azocoupling components.
  • auxiliary agents may be added, for instance, a reducing agent such as thiourea and a stabilizer such as hydroquinone monosulfonic acid.
  • planographic plates A, B, C and D were used. These planographic plates were obtained by sensitizing a planographic layer made according to disclosures of a copending application, Ser. No. 790,174, filed Jan. 9, 1969, which layer was previously formed on a highly glazed paper of 100 g/m in weight by the application of a dispersion containmg:
  • the coating layer was dried and hardened by heating for to 20 seconds at 155 to 160 C., its weight amounted to about 12 g./m.
  • the sensitized plate contained about 0.5 millimole of diazonium salt per m Plate B was sensitized with a solution containing:
  • the sensitized plate contained about 0.5 millimole of diazonium salt per m3.
  • the sensitized plate contained about 0.5
  • Plate D was sensitized with a solution containing:
  • the sensitized plate contained about 0.5 millimole of diazonium saltper m.
  • EXAMPLE I A presensitized plate A was imagewise exposed under a typewritten text on transparent material having a good density for the copying light, until the diazonium compound under the image-free areas of the original had been bleached out. The exposed plate was cut longitudinally into halves and the strips were marked Al and A2.
  • strip Al was developed 'with a developer of the following composition: i l i 7.5 g. of phloroglucinol,
  • Strip A2 was developed with a similar developer from which, however, the n-propylglycol had been omitted. immediately upon development the two strips were clamped side by side onto the plate cylinder of an ofiset printing machine, and 200 prints were made.
  • strip Al showed no initial toning, whereas those of strip A2 showed an intensive initial toning.
  • Analogous results are obtained when strip A1 is developed with a developer of one of the compositions described below and strip A2 with the corresponding developer without any organic solvent:
  • strip B1 was developed with a developer of the following composition:
  • Strip B2 was developed with a corresponding developer without n-propylglycol.
  • EXAMPLE III A presensitized plate C was imagewise exposed as described in example I, and subsequently cut longitudinally into halves to form strips which were marked C1 and C2.
  • Strip C1 was developed with the n-propylglycol-containing developer of example II and strip C2 with the corresponding developer without n-propylglycol. The developers were applied to the strips with a tampon.
  • Strip D2 was developed with a corresponding developerwithout n-propylglycol.
  • the developers were applied to the strips with a tampon.
  • the developed strips were clamped side by side on the plate cylinder of an offset printing machine and 250 prints were made.
  • the first few prints of strip D2 showed much more initial toning than those of strip D1.
  • the image on strip D2 appeared to wear off more quickly.
  • EXAMPLE V A presensitized plate A was imagewise exposed until the diazonium compound under the imagefree areas of the original had bleached out, and was subsequently developed with a developer of the following composition:
  • pH is about 6.2. 9 g. ofphloroglucinol
  • pH of this developer was about 7.
  • the developed plate was clamped on the plate cylinder of the offset printing machine and finally washed with water. More than 200 good prints were obtained. The first few prints had no initial toning.
  • pH is about 4.3.
  • a composition for developing into an oleophilic azodyestuff image an imagewise exposed, light-sensitive planographic printing surface sensitized with a benzene diazonium compound comprising an aqueous solution of phloroglucinol containing buffering salt giving the solution a pH between 4 and 8 and containing l-l0 percent by volume of water-miscible organic solvent selected from the group consisting of npropylglycol, acetonyl acetone, diacetone alcohol and N- methylpyrrolidone-2.
  • composition according to claim 5 said buffering salt comprising at least one alkaline-reacting salt of a weak acid
  • said solution also containing l-lO percent by weight of at least one waterosoluble inorganic salt of a strong acid, which salts do not react together to form a precipitate in said solution.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
US790175A 1968-01-12 1969-01-09 Phloroglucinol developer for lingt-sensitive planographic plates Expired - Lifetime US3607271A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL6800538A NL6800538A (en, 2012) 1968-01-12 1968-01-12

Publications (1)

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US3607271A true US3607271A (en) 1971-09-21

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US (1) US3607271A (en, 2012)
DE (1) DE1900468A1 (en, 2012)
FR (1) FR1602009A (en, 2012)
GB (1) GB1249381A (en, 2012)
NL (1) NL6800538A (en, 2012)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4128423A (en) * 1974-05-29 1978-12-05 Oce-Nederland B.V. Diazotype material that can be developed by applying a small amount of developing liquid, and development thereof
US4370406A (en) * 1979-12-26 1983-01-25 Richardson Graphics Company Developers for photopolymer lithographic plates
US4401747A (en) * 1982-09-02 1983-08-30 J. T. Baker Chemical Company Stripping compositions and methods of stripping resists
US4401748A (en) * 1982-09-07 1983-08-30 J. T. Baker Chemical Company Stripping compositions and methods of stripping resists
US4411983A (en) * 1978-04-25 1983-10-25 Fuji Photo Film Co., Ltd. Method for processing an image-forming material
WO1987007735A1 (en) * 1986-06-09 1987-12-17 Imperial Metal & Chemical Company Additive developer
US5204227A (en) * 1990-05-10 1993-04-20 3D Agency, Inc. Method of developing photopolymerizable printing plates and composition therefor
US5902718A (en) * 1990-04-27 1999-05-11 Mitsubishi Denki Kabushiki Kaisha Methods and developer for developing a positive photoresist
US5985525A (en) * 1992-10-01 1999-11-16 Tokyo Ohta Kogyo Co., Ltd. Developer solution for photoresist composition
US6716884B1 (en) * 2000-05-19 2004-04-06 Promindus (Actions Promotionnelles Dans L'industrie Et Le Commerce) Pharmaceutical compositions for oral administration of phloroglucinol and preparation thereof
EP1179040A4 (en) * 1999-05-11 2004-09-22 Baldwin Graphic System Inc SOLVENT SYSTEMS FOR THE REMOVAL OF INKS AND IMAGE LAYERS FROM PRINTING PLATES AND METHOD FOR THE USE THEREOF

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA804933B (en) * 1979-08-20 1981-07-29 Vickers Ltd Lithographic printing plates
DE3715792A1 (de) * 1987-05-12 1988-11-24 Hoechst Ag Entwickler fuer wasserlos druckende offsetplatten

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1821281A (en) * 1926-12-11 1931-09-01 Frans Van Der Grinten Manufacture of diazo-types
US1841653A (en) * 1927-08-22 1932-01-19 Frans Van Der Grinten Process for developing positive diazo prints
US2113944A (en) * 1933-09-11 1938-04-12 Dietzgen Eugene Co Production of photographic diazotype prints
US2531004A (en) * 1947-11-26 1950-11-21 Gen Aniline & Film Corp Acetonitriles as azo components in diazotypes
US2702242A (en) * 1950-08-13 1955-02-15 Azoplate Corp Method of preparing diazo photolithographic plates
GB1082889A (en) * 1965-07-02 1967-09-13 Grinten Chem L V D Diazotype material and diazonium compounds

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1821281A (en) * 1926-12-11 1931-09-01 Frans Van Der Grinten Manufacture of diazo-types
US1841653A (en) * 1927-08-22 1932-01-19 Frans Van Der Grinten Process for developing positive diazo prints
US2113944A (en) * 1933-09-11 1938-04-12 Dietzgen Eugene Co Production of photographic diazotype prints
US2531004A (en) * 1947-11-26 1950-11-21 Gen Aniline & Film Corp Acetonitriles as azo components in diazotypes
US2702242A (en) * 1950-08-13 1955-02-15 Azoplate Corp Method of preparing diazo photolithographic plates
GB1082889A (en) * 1965-07-02 1967-09-13 Grinten Chem L V D Diazotype material and diazonium compounds

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4128423A (en) * 1974-05-29 1978-12-05 Oce-Nederland B.V. Diazotype material that can be developed by applying a small amount of developing liquid, and development thereof
US4411983A (en) * 1978-04-25 1983-10-25 Fuji Photo Film Co., Ltd. Method for processing an image-forming material
US4370406A (en) * 1979-12-26 1983-01-25 Richardson Graphics Company Developers for photopolymer lithographic plates
US4401747A (en) * 1982-09-02 1983-08-30 J. T. Baker Chemical Company Stripping compositions and methods of stripping resists
US4401748A (en) * 1982-09-07 1983-08-30 J. T. Baker Chemical Company Stripping compositions and methods of stripping resists
WO1987007735A1 (en) * 1986-06-09 1987-12-17 Imperial Metal & Chemical Company Additive developer
US4714670A (en) * 1986-06-09 1987-12-22 Imperial Metal & Chemical Company Developer including an aliphatic cyclic carbonate in the oil phase emulsion
US5902718A (en) * 1990-04-27 1999-05-11 Mitsubishi Denki Kabushiki Kaisha Methods and developer for developing a positive photoresist
US5204227A (en) * 1990-05-10 1993-04-20 3D Agency, Inc. Method of developing photopolymerizable printing plates and composition therefor
US5985525A (en) * 1992-10-01 1999-11-16 Tokyo Ohta Kogyo Co., Ltd. Developer solution for photoresist composition
EP1179040A4 (en) * 1999-05-11 2004-09-22 Baldwin Graphic System Inc SOLVENT SYSTEMS FOR THE REMOVAL OF INKS AND IMAGE LAYERS FROM PRINTING PLATES AND METHOD FOR THE USE THEREOF
US6716884B1 (en) * 2000-05-19 2004-04-06 Promindus (Actions Promotionnelles Dans L'industrie Et Le Commerce) Pharmaceutical compositions for oral administration of phloroglucinol and preparation thereof

Also Published As

Publication number Publication date
FR1602009A (en, 2012) 1970-09-28
GB1249381A (en) 1971-10-13
NL6800538A (en, 2012) 1969-07-15
DE1900468A1 (de) 1969-07-31

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