US3778274A - Spectrally sensitized diazo material - Google Patents

Spectrally sensitized diazo material Download PDF

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Publication number
US3778274A
US3778274A US00132074A US3778274DA US3778274A US 3778274 A US3778274 A US 3778274A US 00132074 A US00132074 A US 00132074A US 3778274D A US3778274D A US 3778274DA US 3778274 A US3778274 A US 3778274A
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United States
Prior art keywords
diazo
sodium
dithiocarbamate
ammonium
photolytic
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Expired - Lifetime
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US00132074A
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English (en)
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E Inoue
T Yamase
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Canon Inc
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Canon Inc
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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
    • G03F7/016—Diazonium salts or compounds
    • G03F7/0166—Diazonium salts or compounds characterised by the non-macromolecular additives
    • 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

  • ABSTRACT A dithiocarbamate is mixed with a photolytic aromatic diazo compound to improve the intrinsic sensitivity and spectral sensitivity of the photosensitive material for diazo photography.
  • Diazo photography is based on the photolysis of aromatic diazo compounds such as diazonium salts, metal complexes thereof and diazosulfonates. If desired, coupling components are used together to produce dye images, print images or bubble images.
  • various diazo photographic processes have been knowii.
  • One of them uses a photolytic diazo compound, a coupling component and a coupling controlling agent.
  • This diazo photographic process is further divided into a wet process and a dry process.
  • a photosensitive paper is used having a coating of a photolytic diazo compound only and after exposure to a light image the photosensitive paper is developed using a solution containing a coupling component.
  • the dry process utilizes a photosensitive paper having a coating containing a photolytic diazo compound, a coupling component and a coupling controlling agent and this is exposed to a light image followed by developing with ammonia gas.
  • a photosensitive member having a photolytic diazo compound dispersed in a thermoplastic binder is exposed to a light image and is then heated to produce a light-scattering image composed of air bubbles.
  • other various modified diazo photographic processes are known.
  • light energy necessary for the photolysis of photolytic aromatic diazo compounds used in the diazo photographic processes is very large and the photosensitive spectrum ranges only up to visible blue region and therefore, these diazo photographic materials can be practically used only as low sensitive ultraviolet printing materials.
  • the present invention solves the above mentioned problems and increases the intrinsic sensitivity and the spectral sensitivity of the photolysis of photolytic aromatic diazo compounds.
  • R, and R may be, similar or dissimilar, selected from the group consisting of hydrogen, a substituted or an unsubstituted alkyl, a substituted or an unsubstituted alkenyl, a substituted or an unsubstituted cycloalkyl, substituted or an unsubstituted aralkyl, a substituted or an unsubstituted aryl, a substituted or an unsubstituted S-membered heterocyclic ring radical, and a substituted or an unsubstituted 6-membered heterocyclic ring radical, and R and R taken together, may form a ring;
  • R; is a divalent organic radical, for example, a divalent hydrocarbon radical such as alkylene, phenylene and the like; and M is, similar or dissimilar, selected from the group consisting of a hydrogen ion, a metal ion, an ammonium ion, and an organic c
  • the photosensitive material may contain additionally a sensitizing dye.
  • CHT-CHQ These compounds may be prepared from the corresponding amine and carbon disulfide. Some detailed methods for preparation thereof are described in RE- CUEIL, 917-939 (1951) and Journal Praktician Chemie", 67 286-287 (1903).
  • sensitizing dyes such as those used for sensitizing silver halides and zinc oxide may be used in this invention.
  • triphenylmethane dyes such as Brilliant Green, Crystal Violet and Acid-Violet 6B
  • rhodamines such as Rhodamine B, Rhodamine 6G, Rhodamine G Extra, Sulforhodamine B and First-Acid-Eosine G
  • xanthene dyes such as Eosine S, Eosine A, Erythrosine, Phloxine, Rosebengale and fluorescein
  • thiazine dyes such as methylene blue, methylene green, methylene violet, methylene azine, thionine blue, toluidine blue, and Thiocarmine R
  • acridine dyes such as acridine yellow, acridine orange and Trypaflavin
  • quinoline dyes such as pinacyanol and cryptocyanine
  • quinone dyes
  • thia-' zine dye, xanthene dye, and acridine dye are preferably used to increase spectral sensitivity.
  • photolytic aromatic diazo compounds are used in this invention and sensitized by the addition of a dithiocarbamate (I) or (II) and a sensitizing dye, conventional photolytic aromatic diazo compounds usable in diazo photography may also be used.
  • P-diazo mono (or di-) alkylaniline derivatives such as: p-diazo methylaniline hydrochloride, p-diazo dimethylaniline hydrochloride, p-diazo ethylhydroxylethylaniline hydrochloride, p-diazo m-chloro diethylaniline hydrochloride, and p-diazo o-methoxy diethylaniline sulphate;
  • P-diazo diphenylamine derivatives such as p-diazo diphenylamine sulphate
  • Diazo polymer such as the condensation product of p-diazo diphenylamine and formaldehyde in sulfuric acid.
  • the dithiocarbamate and the sensitizing dye may be incorporated in a photosensitive layer of a photosensitive member of diazo photography.
  • the amount of dithiocarbamate to be added to a photolytic aromatic diazo compound is not critical. However, it is preferable to use from 0.5 to 10 moles of dithiocarbamate per one mole of diazo compound.
  • a diazonium salt or diazo sulfonate, a coupler, a stabilizer and other additives are made into an aqueous solution or an aqueous alcoholic solution, and a dithiocarbamate and, if desired, a sensitizing dye are added thereto, and the resulting mixture is coated on a support such as paper and film and dried.
  • This diazo photosensitive material is then exposed to a light image and developed with ammonia gas to produce an azo dye image at a non-exposed portion.
  • a photosensitive material excluding a coupler is used, the diazo photosensitive member exposed to a light image is developed by an aqueous alkaline solution of a coupler to produce an azo dye image.
  • the preparation of the photosensitive member is carried out in a dark room.
  • Formulation of conventional diazo photosensitive material may be employed except than a dithiocarbamate and, if desired, a sensitizing dye are added.
  • a dithiocarbamate and, if desired, a sensitizing dye are added.
  • the details are described in Kagaku Shashin Binran (Handbook of Scientific Photograp y), edited by Shinichi Kikuchi, 2nd Volume, pages 335 337.
  • a diazo photosensitive material for bubble photography may be prepared by adding a dithiocarbamate and, if desired, a sensitizing dye to a photosensiteve material formulation of conventional bubble photography.
  • a diazonium salt, a dithiocarbamate and a sensitizing dye are added to a solution of a hydrophobic binder resin, coated on a film and dried.
  • the diazonium salt and the dithiocarbamate are preferably soluble in organic solvents.
  • Sample 1 Sample 2 and Sample 3 are placed in test tubes, and exposed to a 1 KW tungsten lamp at a distance of 20cm. through an infrared! ray absorbing filter HR-l-69 (trade name, supplied by Dow Corning) and a Toshiba Glass Filter VR-62 (trade name, supplied by Toshiba).
  • HR-l-69 trade name, supplied by Dow Corning
  • a Toshiba Glass Filter VR-62 trade name, supplied by Toshiba
  • Samples 1, 2 and 3 are impregnated in filter paper, dried by air-blowing at a' temperature below 50C and irradiated by a 1 KW tungsten lamp through the above mentioned filter, and then sprayed with an alkaline solution of Bmaphthol. As a result, Sample 1 and Sample 2 become reddish purple while no color is observed in Sample 3.
  • An aqueous solution containing 4- diazodiphenylamine sulfate (5 X 10* mole/1.), hexamethylene ammonium hexamethylene dithiocarbamate (l X lO' mole/l and Methylene Blue (2 X l0mole/l.) is adjusted to pH 6.0 by using a phosphoric acid buffer solution.
  • the absorption spectra of the resulting solution is measured at sample thickness of 10 u and absorption peaks at 680, 650, 380, 300 and 25 p. are found.
  • the former paper containing the dithiocarbamate gave images free from fog at a rapid speed about twice that of the paper not containing dithiocarbamate.
  • Photosensitive papers were prepared by using the formulations as shown in Table 1 below in a way similar to Example 1:, irradiated by a 20 W blue fluorescent lamp at a distance of 20 cm. and developed with ammonia a reciprocal of exposure time (seconds) required for obtaining 0.05 of density of background was obtained.
  • Table 1 below in a way similar to Example 1:, irradiated by a 20 W blue fluorescent lamp at a distance of 20 cm. and developed with ammonia a reciprocal of exposure time (seconds) required for obtaining 0.05 of density of background was obtained.
  • the Table 1 below shows the relative sensitivity referring to the control sample.
  • EXAMPLE 4 1000 ml. of an aqueous solution containing 10g. of 4-benzoylamino-3,S-diethoxybenzene diazonium chloride and 10g. of thiourea was prepared. To this aqueous solution 30g. of hexamethylene ammonium hexamethylene dithiocarbamate and 1.0g. of Rose Bengal were added and it was coated on a paper and dried. In a way similar to Example 3, the resulting photosensitive paper was contacted with an original and exposed, and then soaked in an aqueous solution (l000 ml.) containing 10g. of sodium l-naphthol-4-sulfonate, 20g. of sodium carbonate and 25g. of borax, squeezed by a rubber roller and dried. A clear bluish purple image was obtained.
  • aqueous solution containing 10g. of sodium l-naphthol-4-sulfonate, 20g. of sodium carbonate and 25g. of
  • EXAMPLE 6 A solution composed of l0.0g. of polyvinylidene chloride, 2.0g. of polymethylmethacrylate and 50 ml. of methyl ethyl ketone was prepared, and to the resulting solution was added a solution (12 ml.) of 1.5g. of p-dimethylaminobenzene diazonium chloride zinc chloride complex in methanol.
  • a methanol solution ml.) containing 0.5g. of sodium N, N-diphenyldithiocarbamate and 0. lg. of Rose Bengal was added thereto and the resulting mixture solution was immediately coated on a polyester film of 75p. in an amount to form a coating of about lOu thick when dried, and dried at a temperature below 70C.
  • the resulting photosensitive film was closely contacted with a negative microfilm and exposed in a way similar to that of Example 3, followed by its being pressed with a roller at 120C for about one second to produce a light-scattering image composed of nitrogen bubble at the exposed portion.
  • EXAMPLE 7 Diazo resin (3.0g), obtained by condensing p-phenyl-aminobenzene diazonium sulfate and paraformaldehyde in a dark and cool place was dissolved in a 50 percent aqueous solution of methanol. To the resulting solution were successively added 1.0g. of morphorinoethyl dithiocarbamic acid and 100 mg. of Rose Bengal and then the resulting solution was coated on a sand blasted aluminum plate and dried. The resulting photosensitive plate was closely contacted with a negative original and exposed by using a 500W flood lamp at a distance of 50 cm. for 3 minutes, followed by developing it with an aqueous methanol to harden the diazo resin at the exposed portion to produce an offset printing plate.
  • a photosensitive composition for diazo photography comprising in combination a photolytic aromatic diazonium salt and at least one member selected from the group consisting of dithiocarbamates of the formulas l and II,
  • R and R are similar or dissimilar radicals, selected from the group consisting of hydrogen, alkyl, cyclohexyl, aralkyl having a benzene nucleus or naphthalene nucleus, phenyl, morpholinoethyl, 1- piperidinylethyl and R and R when taken together with the nitrogen atom to which it is attached, form a 5, 6 or 7 membered saturated heterocyclic ring;
  • R is a divalent organic radical
  • M is a similar or dissimilar radical, selected from the group consisting of a hydrogen sodium, potassium, cadmium, and zinc atoms
  • ammonium ion and monovalent organic radical substituted ammonium where said radical is an alkyl, cyclohexyl group or together with the nitrogen atom to which it is attached, forms a saturated heterocyclic ring containing six carbon atoms.
  • a photosensitive material composition for diazo photography according to claim 1 in which the photolytic aromatic diazonium salt is .a member selected from the group consisting of pdiazo mono (or di-) alkylaniline derivatives, 2, 5- disubstituted-4-diazo-N- acyl anilides, p-diazo diphenylamine derivatives.
  • a photosensitive material for diazo photography according to claim 1 in which the dithiocarbamate is a member selected from the group consisting of sodium methyldithiocarbamate, ammonium methylenedithiocarbamate, ethylammonium ethyldithiocarbamate, zinc dimethyldithiocarbamate, sodium octyldithiocarbamate, cyclohexylammonium cyclohexydithiocarbamate, cadmium cyclohexyldithiocarbamate, ammonium propenyldithiocarbamate, potassium octenyldithiocarbamate, sodium benzyldithiocarbamate, ammonium methylbenzyldithiocarbamate, ammonium naphthylmethyldithiocarbamate, ammonium phenyldithiocarbamate, diphenyldithiocarbamic acid, sodium dipheny
  • a photosensitive composition for diazo photography which comprises a photolytic aromatic diazonium salt, at least one member selected from the group consisting of dithiocarbamates of the formulas l and II,
  • R and R are, similar or dissimilar radicals, selected from the group consisting of hydrogen, alkyl, cyclohexyl, aralkyl having a benzene nucleus or naphthalene nucleus, phenyl, morpholinoethyl, 1- piperidinylethyl, and R and R when taken together with a nitrogen atom to which it is attached form a 5, 6 or 7 membered saturated heterocyclic ring;
  • R5 is a divalent organic radical
  • M is a similar or dissimilar radical, selected from the group consisting of a hydrogen sodium, potassium, cadmium, and zinc atoms, ammonium ion, and monovalent organic radical substituted ammonium where said radical is an alkyl, cyclohexyl group or together with the nitrogen atom to which it is attached forms a saturated heterocyclic ring containing six carbon atoms, and at least one sensitizing dye selected from the group consisting of triphenylmethane dye,

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  • General Physics & Mathematics (AREA)
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  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4105450A (en) * 1973-07-27 1978-08-08 Fuji Photo Film Co., Ltd. Spectrally sensitized positive light-sensitive o-quinone diazide containing composition
US4147552A (en) * 1976-05-21 1979-04-03 Eastman Kodak Company Light-sensitive compositions with 3-substituted coumarin compounds as spectral sensitizers
US4248959A (en) * 1978-12-07 1981-02-03 American Hoechst Corporation Preparation of diazo printing plates using laser exposure
US4268600A (en) * 1977-12-09 1981-05-19 Issec and Tissages de Soieries Rennis Process for photochemically coloring textiles using photosensitive triazene and coupler therefor
US4268603A (en) * 1978-12-07 1981-05-19 Tokyo Ohka Kogyo Kabushiki Kaisha Photoresist compositions
US4356255A (en) * 1979-06-28 1982-10-26 Fuji Photo Film Co., Ltd. Photosensitive members and a process for forming patterns using the same
US4486529A (en) * 1976-06-10 1984-12-04 American Hoechst Corporation Dialo printing plate made from laser
US4542085A (en) * 1982-06-02 1985-09-17 Fuji Photo Film Co., Ltd. Negative working diazo light-sensitive composition with oxonol dye and lithographic printing plate using the same
US4544627A (en) * 1978-10-31 1985-10-01 Fuji Photo Film Co., Ltd. Negative image forming process in o-quinone diazide layer utilizing laser beam
US4770973A (en) * 1985-11-15 1988-09-13 Kanzaki Paper Manufacturing Limited Heat-sensitive diazo recording material with diphenyl alkene coupler
US4929534A (en) * 1987-08-31 1990-05-29 Hoechst Aktiengesellschaft Positive-working photosensitive mixture and photolithographic copying material produced therefrom with o-quinone dialide sulfonyl ester and azo coupler
US4980263A (en) * 1988-03-03 1990-12-25 Fuji Photo Film Co., Ltd. Light-sensitive diazo resin composition with polyurethane and compound having ureido, thioureido, urethane, or thiourethane unit
US5344739A (en) * 1991-11-01 1994-09-06 Nippon Paint Co., Ltd. Photosensitive diazo resin composition for lithographic printing utilizing a xanthene dye having an anion group as the counter ion of the diazonium group
US5545676A (en) * 1987-04-02 1996-08-13 Minnesota Mining And Manufacturing Company Ternary photoinitiator system for addition polymerization

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0675941U (ja) * 1993-04-03 1994-10-25 備前発条株式会社 傾斜地軌条運搬車

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1803906A (en) * 1928-02-16 1931-05-05 Kalle & Co Ag Diazo-types stabilized with alpha derivative of thiocarbonic acid and alpha processof preparing them
US1821306A (en) * 1928-12-08 1931-09-01 Frans Van Der Grinten Apparatus for applying thin even layers of liquids on surfaces
US2423520A (en) * 1943-10-06 1947-07-08 Du Pont Photopolymerization of vinylidene compounds in the presence of n-disubstituted dithiocarbamic esters
US2755185A (en) * 1953-11-23 1956-07-17 Gen Aniline & Film Corp Method of improving rate of ammonia development of light sensitive diazotype materials
US2875047A (en) * 1955-01-19 1959-02-24 Oster Gerald Photopolymerization with the formation of coherent plastic masses
US2996381A (en) * 1957-07-02 1961-08-15 Kalvar Corp Photographic materials and procedures for using same
US3070442A (en) * 1958-07-18 1962-12-25 Du Pont Process for producing colored polymeric relief images and elements therefor
US3099558A (en) * 1959-06-26 1963-07-30 Gen Aniline & Film Corp Photopolymerization of vinyl monomers by means of a radiation absorbing component in the presence of a diazonium compound
US3260599A (en) * 1962-11-19 1966-07-12 Minnesota Mining & Mfg Vesicular diazo copy-sheet containing photoreducible dye
US3288627A (en) * 1965-08-05 1966-11-29 Addressograph Multigraph Heat-sensitive diazotype material coated sheet
US3406072A (en) * 1964-12-21 1968-10-15 Gaf Corp One-component diazotypes
US3418118A (en) * 1965-06-03 1968-12-24 Du Pont Photographic processes and products
US3615452A (en) * 1968-09-09 1971-10-26 Gaf Corp Dye-sensitized photopolymerization process
US3622326A (en) * 1968-03-07 1971-11-23 Ricoh Kk Diazotype light-sensitive copying papers intended for wet development and for use in the preparation of intermediates
US3718467A (en) * 1971-03-25 1973-02-27 Canon Kk Positive working photographic process for producing colored images of metal chelates of sulfur compounds

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1803906A (en) * 1928-02-16 1931-05-05 Kalle & Co Ag Diazo-types stabilized with alpha derivative of thiocarbonic acid and alpha processof preparing them
US1821306A (en) * 1928-12-08 1931-09-01 Frans Van Der Grinten Apparatus for applying thin even layers of liquids on surfaces
US2423520A (en) * 1943-10-06 1947-07-08 Du Pont Photopolymerization of vinylidene compounds in the presence of n-disubstituted dithiocarbamic esters
US2755185A (en) * 1953-11-23 1956-07-17 Gen Aniline & Film Corp Method of improving rate of ammonia development of light sensitive diazotype materials
US2875047A (en) * 1955-01-19 1959-02-24 Oster Gerald Photopolymerization with the formation of coherent plastic masses
US3097096A (en) * 1955-01-19 1963-07-09 Oster Gerald Photopolymerization with the formation of relief images
US2996381A (en) * 1957-07-02 1961-08-15 Kalvar Corp Photographic materials and procedures for using same
US3070442A (en) * 1958-07-18 1962-12-25 Du Pont Process for producing colored polymeric relief images and elements therefor
US3099558A (en) * 1959-06-26 1963-07-30 Gen Aniline & Film Corp Photopolymerization of vinyl monomers by means of a radiation absorbing component in the presence of a diazonium compound
US3260599A (en) * 1962-11-19 1966-07-12 Minnesota Mining & Mfg Vesicular diazo copy-sheet containing photoreducible dye
US3406072A (en) * 1964-12-21 1968-10-15 Gaf Corp One-component diazotypes
US3418118A (en) * 1965-06-03 1968-12-24 Du Pont Photographic processes and products
US3288627A (en) * 1965-08-05 1966-11-29 Addressograph Multigraph Heat-sensitive diazotype material coated sheet
US3622326A (en) * 1968-03-07 1971-11-23 Ricoh Kk Diazotype light-sensitive copying papers intended for wet development and for use in the preparation of intermediates
US3615452A (en) * 1968-09-09 1971-10-26 Gaf Corp Dye-sensitized photopolymerization process
US3718467A (en) * 1971-03-25 1973-02-27 Canon Kk Positive working photographic process for producing colored images of metal chelates of sulfur compounds

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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4105450A (en) * 1973-07-27 1978-08-08 Fuji Photo Film Co., Ltd. Spectrally sensitized positive light-sensitive o-quinone diazide containing composition
US4147552A (en) * 1976-05-21 1979-04-03 Eastman Kodak Company Light-sensitive compositions with 3-substituted coumarin compounds as spectral sensitizers
US4486529A (en) * 1976-06-10 1984-12-04 American Hoechst Corporation Dialo printing plate made from laser
US4268600A (en) * 1977-12-09 1981-05-19 Issec and Tissages de Soieries Rennis Process for photochemically coloring textiles using photosensitive triazene and coupler therefor
US4544627A (en) * 1978-10-31 1985-10-01 Fuji Photo Film Co., Ltd. Negative image forming process in o-quinone diazide layer utilizing laser beam
US4268603A (en) * 1978-12-07 1981-05-19 Tokyo Ohka Kogyo Kabushiki Kaisha Photoresist compositions
US4248959A (en) * 1978-12-07 1981-02-03 American Hoechst Corporation Preparation of diazo printing plates using laser exposure
US4356255A (en) * 1979-06-28 1982-10-26 Fuji Photo Film Co., Ltd. Photosensitive members and a process for forming patterns using the same
US4542085A (en) * 1982-06-02 1985-09-17 Fuji Photo Film Co., Ltd. Negative working diazo light-sensitive composition with oxonol dye and lithographic printing plate using the same
US4770973A (en) * 1985-11-15 1988-09-13 Kanzaki Paper Manufacturing Limited Heat-sensitive diazo recording material with diphenyl alkene coupler
US5545676A (en) * 1987-04-02 1996-08-13 Minnesota Mining And Manufacturing Company Ternary photoinitiator system for addition polymerization
US6017660A (en) * 1987-04-02 2000-01-25 3M Innovative Properties Company Inks containing a ternary photoinitiator system and image graphics prepared using same
US4929534A (en) * 1987-08-31 1990-05-29 Hoechst Aktiengesellschaft Positive-working photosensitive mixture and photolithographic copying material produced therefrom with o-quinone dialide sulfonyl ester and azo coupler
US4980263A (en) * 1988-03-03 1990-12-25 Fuji Photo Film Co., Ltd. Light-sensitive diazo resin composition with polyurethane and compound having ureido, thioureido, urethane, or thiourethane unit
US5344739A (en) * 1991-11-01 1994-09-06 Nippon Paint Co., Ltd. Photosensitive diazo resin composition for lithographic printing utilizing a xanthene dye having an anion group as the counter ion of the diazonium group

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DE2117044B2 (de) 1976-07-15
JPS4918809B1 (enrdf_load_stackoverflow) 1974-05-13
DE2117044A1 (de) 1971-10-21

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