US3016298A - One-component diazotype material - Google Patents

One-component diazotype material Download PDF

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Publication number
US3016298A
US3016298A US742025A US74202558A US3016298A US 3016298 A US3016298 A US 3016298A US 742025 A US742025 A US 742025A US 74202558 A US74202558 A US 74202558A US 3016298 A US3016298 A US 3016298A
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acid
diazo
diazotype
compound
coupling
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Sanders Theodorus Pe Wilhelmus
Ronc Hubertus Wilhelmus Maria
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Chemische Fabriek L Van der Grinten NV
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Grinten Chem L V D
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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
    • G03C1/00—Photosensitive materials
    • G03C1/52—Compositions containing diazo compounds as photosensitive substances
    • G03C1/54—Diazonium salts or diazo anhydrides
    • 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

  • actively coupling diazo compounds are-compounds such as p-diazo N.N'-dimethylaniline, pdiazoNN-diethylanilinc, p-diazo m.methylN.N-dimethylaniline, and"diazo anhydrides such as Z-diazo-l-naphtholsulphonic"acid.
  • actively coupling diazo compounds are-compounds such as p-diazo N.N'-dimethylaniline, pdiazoNN-diethylanilinc, p-diazo m.methylN.N-dimethylaniline, and”diazo anhydrides such as Z-diazo-l-naphtholsulphonic"acid.
  • the coupling liquid of, forexam'ple, 8 g. per rn. developing;
  • thedittzo compounds can be determined com- 'paratively invitro'by measuring the time in which a I given portion (for'exarnple, 10%) of .the diazo com- ;pound 'to-be 'examinedwill have coupled in a given molar concentration (for example, 0.1 millimolar) with the couplingconipone'nt l-ph'enyI S-methyl pyrazolon'e-(S) in a"given molarco'ncentration (for example, 1.0 ,milliniolaryin shutter mixture of a given composition and agivenipl'l at'a given temperature.
  • molar concentration for example, 0.1 millimolar
  • the couplingconipone'nt l-ph'enyI S-methyl pyrazolon'e-(S) in a"given molarco'ncentration for example, 1.0 ,milliniolaryin shutter mixture of a given composition and agiveni
  • a developing liquid reacting moderately alkaline has a pH between 8 and 11 and contains alkali salts, such as bonus, car'- bonates, and phosphates.
  • the couplingcomponent it contains is generally phloroglucin'ol, a very actively coupling compound, which is able to'couple at one, two" or three places with the'diazo compound and in proportion thereto forms deystutfs of various shades.
  • Etforts have been made to manufacture with the said very actively coupling diazo compounds diazotype materia'lswhich are suitedtor semi we't development with the said developers reacting moderately alkaline, and
  • the sensitizing liquids for the manufacture of diazotype" material's-with thesefdiazo compounds usually contain only approximately 05-1 of their weight of the acids normally used in one-component diazotype layers, such as tartaric acid, citric acid, aluminum sulphate, alum, and the'like, and the diazotype materials produced therewith 1 are; then suited for semi-wet development with weakly I alkaline to weakly acidic buttered developers, they have l to contain about 3 to 4% of these acids for the manufacture of diazotype materials which are suited for the.
  • the butierin'g capacity of the light-sensitive layer of one-component diazotype materials which contain so large a quantity of such an acid is higher than that of the corresponding-materialscontaining a small amount of acid, it is nevertheless insuflielent for the practice of the semi-wet diazotype process with the said developers reacting'm ofclrately alkaline.
  • the materials are verysensitive to development fluctuations when such" developers containing polyvalent azo coupling components, such as phloroglucinol, are used. These fluctuations generally arise because the quantityof developer applied itself fluctuates, for example, owing to shocks or vibrations of the developing apparatus or when its speed is changed.
  • diazo film layers In order to avoid the objectionable consequences of development fluctuations in the semi-wet development of diazo film layers, it has been proposed to sensitize diazo film layers with a p-diazo-dialkylaminobenzene compound each-alkyl group of which .containsat least 4 and 'at most 7 C-atoms, while both alkyl groups contain together 10, 11 or 12 C-atoms and at most one of the two alkyl, groups carries a side-chain attached to the a-C- atom.
  • These diazo compounds couple actively and the diazo film layers sensitized with them are suited for the semi-wet development with the said developers reacting moderately alkaline.
  • These diazo film layers contain very small quantities of the acids normally used in the diazotype process, such as tartaric acid, citric acid, and alum.
  • a one-component diazotype material has a light-sensitive layer which contains a diazo compound coupling at least as actively as p-diazo diphenylamine, preferably a diazo compound that can readily couple with phloroglucinol in an acid mediumand an aliphatic saturated dicarboxylic acid in which the carboxylic acid groups are linked with two carbon atoms which form part of a hydrocarbon radical that may or may not be substituted and which has 2 to 8 carbon atoms, which acid has electrolytic dissociation constants smaller than 2.3 X 10- the said light-sensitive layer containing a quantity of said acid equimolarly corresponding to at least 0.20 g. of succinic acid per m of its lightsensitive surface.
  • a diazo compound coupling at least as actively as p-diazo diphenylamine preferably a diazo compound that can readily couple with phloroglucinol in an acid mediumand an aliphatic saturated dicarboxylic acid in which the carboxylic acid
  • diazotype material according to the invention Semi-wet development of said diazotype material with the usual developers reacting moderately alkaline yields azo-dyestuffs with attractive pure (and neutral) shades ofcolour. Fluctuations in the application or concentration of the developer have a much smaller influence on the shade of the azo-dyestuifs when diazotype material according to the invention is used than if use is made of similar diazotype materials containing the usual acids, such as citric acid and tartaric acid. Upon ageing, diazotype material according to the invention furthere shows less loss of its mechanical strength.
  • one-component diazotype material By the useof one-component diazotype material according to the invention'it is possible to achieve, with one and the same developer reacting moderately alkaline,.a substantially complete development-which is only slightly affected, if at,all, by development fluctuations-both of transparent diazotype material sensitized with actively coupling diazo compounds which upon semi-wet development give azo-dyestufls with a high absorption for ultraviolet light, such as p-diazo o-chloro N.N-d iethylanilinc, and of diazotype material sensitized with very actively coupling diazo compounds, such as 4-diazo 2,5-dialkoxy acylanilides, 4-diazo 2,5-dlalkoxy arylmercaptobenzene compounds, and 4-diazo 2,5-dialkoxy diphcnyl compounds;
  • the very actively coupling con1- pounds of the said groups yield azo-dyestutls which are highly resistant to oxidation and to the action of light.
  • the photo-decomposition products which remain in the exposed portions of the diazotype copy afterthe imagewise exposure of the diazotype material sensi-- tized with these very actively coupling diazo compounds are highly resistant to oxidation or to the action of light.
  • the azo-dyestufls of the said very actively coupling diazocompounds do not, however, have high absorption for ultra-violet light, so that these diazo compounds are not particularly suited for the sensitization of transparent diazotype materials which are used for the production of intermediate copies.
  • other actively coupling compounds such as p-diazo o-chloro N.N-diethylaniline and p-diazo o-methyl N.N-diethylariilinc, which with phloroglucinol and resorcinol yield a'zo-dyestuffs which possess very high absorption for ultra-violet light and which are therefore very suitable for the manufacture of transparent diazotype material.
  • Such transparent material is not suited for semi-wet development with weakly alkaline to weakly acidic buffered developers, because during development the pH of the surface of the diazotype material is still too low in relation to the coupling activity of the diazo compound, though this activity acumen is large.
  • the diazo compound is not completely converted into azo-dyestulf. This is called underdevelopment.
  • Said transparent diazoty'pe' materials are, however, well suited for semi-wet development with the said developers reacting moderately alkaline.
  • transparent and non-transparent diazotype materials are preferably developed with one and the same developer.
  • the acids included in the diazotype material according to the invention are in general readily available. Those as methyl alcohol, ethyl alcohol, acetone, and the like.
  • the diiferences'between the two dissociation constants of the said aliphatic saturated dicarboxylic acids are con siderably smaller than those present in other organic dior tricarboxyli'c acids, such as oxalic acid, tartaric acid, citric acid ormaleic acid.
  • the last-mentioned acids have a-first electrolytic dissociation constant which is considerably greater than 23x10".
  • the hydrocarbon radical with which the two carboxylic acid groupsin the acids applied'in the diazotype material according to' the invention, are linked may or may not be branched; it is also possible for one or more hydrogen atoms of the hydrocarbon radical to be replaced by groups other than carboxylic acid groups, for example, by amino-, mono-, and dialkylamino groups; the carboxylic acid groups may be linked with two adjacent carbon atoms or with two carbon atoms which are further apart.
  • Suitable acids are, for example, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, az elaic acid, sebacic aid, anti-dimethyl succinic acid, ethyl-succinic acid, fi,B-di1nethyl glutaric acid,
  • the acid content of thelight-sensitivelayer of onecomponent diaz'otype material according to the invention may vary according to the variation of the diazo content.
  • a precise quantity of these acids is necessary when a given developer reacting moderately alkaline is used.
  • a small excess of the acids 'causes under-development, a small shortage of the acids causes over-development.
  • the acid content of the one-component diazotype material according to the invention may vary within much wider limits without causingoveror under-development.
  • one-component diazotype material For the manufacture of one-component diazotype material according to the invention it is not necessary to replace the quantity of citric acidfor other conventional acid in a given one-component diazotype material by'an equivalent quantity of acid according to the invention. It is possible to use considerably more than theequivalent quantity of the last-mentioned acid. I The larger the quantity-of this acid that can be applied, the better' can the detrimental consequences of development fluctuations be avoided, while the drawbacks involved in a high acid content of the light-sensitive layer do not appear or, in a much lower degree, than if use is made of a similar diazotype material with a high content of a conventional acid, such as citric acid or tartaric acid.
  • X is an anion and R an alkyl or aralkyl group.
  • the acyl group may be, for example, acetyl, propionyl, benzoyl, p-chloro-benzoyl, phenyl-acetyl or phenoxy'acetyl.
  • a familiar compound of this type is, for example, the 4-benzoylamino 2,5-diethoxybenzene diazonium chloride, zinc chloride double salt.
  • One-component diaptypematerial according to the invention in which the actively coupling dianocompound is a compound of the type: I i
  • the actively coupling diazo compound is a compoundof the type in which X is an anion, R an alkyl or aralkyl group, and R anarylgroup that may or may not be substituted.
  • X is an anion
  • R an alkyl or aralkyl group and R anarylgroup that may or may not be substituted.
  • A-suitable compound of this type is, for example, 1-
  • Attractive black azo-dyes tutt images can thus be obtained with one-component diazotype material according to the invention the light-sensitive layer of which con- -tains a xanthine.
  • the diazotype material according to the invention may contain the auxiliary substances commonly used in onecomponent diazotype materials, for example, means preventing the discoloration of diazotype copies, such as thiourea, constituents facilitating the sensitization, such as gelatin, gum arabic and isopropyl alcohol; substances which prevent curling, such as glycerol and polyethylene glycol; means promoting the uniformity of the light-sensitive layer, such as dispersions of silica, aluminium oxide, titanium dioxide, barium sulphate, synthetic resins and unboiled starches such as rice starch; means preventing ink-feathering in writing or drawing on copies on such.
  • auxiliary substances commonly used in onecomponent diazotype materials for example, means preventing the discoloration of diazotype copies, such as thiourea, constituents facilitating the sensitization, such as gelatin, gum arabic and isopropyl alcohol; substances which prevent curling, such as glycerol and polyethylene glycol; means promoting the uniformity of
  • sym. diaryl- 7 guanidines for example, sym. diphenylguanidine'
  • stabilizers for example, acids oracid salts such as citric acid, tartaric acid, alum and 1.3.6-naphtalene trisulphonic acid.
  • acids oracid salts such as citric acid, tartaric acid, alum and 1.3.6-naphtalene trisulphonic acid.
  • one-component diazotype material' the light-sensitive layer of which contains a mixture of boric acid and an organic hydroxy acid capable of forming a complex with boric acid.
  • Example I I White base-paper for the diazotype process of weight 80 g ./m. is sensitized with a solution of:
  • the sensitized surface contains approximately 0.2 g. of
  • This developing liquid has a pH of 9.4.
  • the developed copy shows a strong black posifiv image on a foggy background. If the concentration of the constituents of this developer has increased, for example, in consequence of evaporation of the developer in the developing apparatus, to such an extent that the original volume of 1050 cm. has decreased to about 700 cm. upon development of a copy'on this light-sensitive material in an otherwise similar way an image is obtained of which the shade of the azo-dyestuif does not deviate substantially from that of the image obtained with the normally concentrated developer.
  • Example II White base-paper for the diazotype process of weight 80 g./m. is sensitized with a solution of:
  • the sensitized surface contains approximately 0.21 g. of the diazo compound and approximately 0.45 g. of glutaric acid per m
  • a sheet of the diazotype paper is imagewise described in Example I.
  • the imagewise exposed sheet is developed by applying approximately 8 g./m. of the following developing liquid:
  • the developed copy shows a strong black positive image on a foggy background with little variation of shade in consequence of development fluctuations. If, instead of 45 g. of glutaric acid, 33 g. of ortho-phosphoric acid or 50 g. of alum or 40 g. of aluminium sulphate is used exposed as in the sensitizing liquid, considerable variations in azodyestufi shade owing to development fluctuations are obtained.
  • the sensitized surface contains approximately 0.28 g. of the diazo' compound and approximately 0.9 g. of s'ubcric acid per m.
  • a sheet of the diazotype paper is exposed under a transparent original drawn in ink until the ortions of the light- -sensitive layer lying under the transparent portions" of the original are completely bleached out.v
  • the developing liquid has a pH of 9.4.
  • the developed copy shows a strong black positive image on a bright white backgro'ri'nd with few deviations in shade, if any, in consequence of vibrations and mechanical irregularities of the developing apparatus.
  • the sensitized surface contains about 0.15 g. of themercapto-diazo compound, about-0.05 g. of the acylamido diazo compound, about 0.4 g. of succinic acid and about 0.12 g. of adipic acid per m.
  • I II I A sheet of thediazotype paper is exposed and developed as described in Example I. I I II I I ,I I
  • the developed copy shows a strong black image on a foggy background with little variation of shade in consequence, of development fluctuations.
  • Example VI White base-paper for the diazotype process of 80 g./m. is sensitized with a solution of: I 23 g. of p4'-methyl phenylnaei'capto as-dreamy benzene diazonium chloride, zinc chloride double salt weight .20 g. of caffeine 30 g. of succinic acid cinic acid per m 10 20 cm. of a dispersion of polyvinyl acetate (Rhodopa 6000) in 1000 cm. of water and dried.
  • the sensitized surface contains approximately 0.2 g. of the diazo compound and approximately 0.26 g. of suc- A sheet of the diazotype paper is irnagewise exposed as described in Example I.
  • the imagew'ise exposed sheet is developed by applying approximately 8 gJm. of the following developing liquid:
  • X is an anion
  • R is a radical selected from the group consisting of alkyl and aralkyl radicals
  • Y is a radical selected from the group consisting of acylamino, arylmerca'pto, and aryl radicals
  • X is an anion
  • R is a radical selected from the group consisting of alkyl and aralkyl radicals
  • Y is a radical selected from the group consisting of acylamino, arylmerca'pto, and aryl radicals
  • a one-component diazotype material comprising paper having a fibrous side thereof sensitized by a lightsensitive composition containing, and in the absence of an 2120 coupling component, an actively coupling lightsensitive diazo compound of the formula of said side.
  • a one-component diazotype material comprising paper having a fibrous side thereof sensitized by a light- .sensitive composition containing, and in the absence of an azo coupling component, an actively coupling lightsensitive diazo compound of the formula XN SRi in which X isan anion, R is a radical selected from the group consisting of alkyl and aralkyl radicals and R is an aryl radical, and containing with said compound an aliphatic saturated dicarboxylic acid in which the carboxylic acid radicals are linked with two carbon atoms forming part of a hydrocarbon radical having from 2 to 8 carbon atoms, the electrolytic dissociation constants of said acid being smaller than 2.3x said composition providing at least 1.7 millimols of said acid per square meter of the area of said side.
  • a one-component diazotype material comprising paper having a fibrous side thereof sensitized by a lightsensitive composition containing, and in the absence of an azo coupling component, an actively coupling light-sensitive diazo compound of the formula in which X is an anion, R is a radical selected from the group consisting of alkyl and aralkyl radicals and R is an aryl radical, and containing with said compound an aliphatic saturated dicarboxylic acid in which the carin which X is an anion, R is a radical selected from the group consisting of alkyl and aralkyl radicals, and Y is a radical selected from the group consisting of acylamino, arylmercapto, and aryl radicals, and containing with said compound an aliphatic saturated dicarboxylic acid in which the carboxylic acid radicals are linked with two carbon atoms forming part of a hydrocarbon radical having from-2 to 8 carbon atoms,-the electrolytic dissociation constants of said acidbeing smaller
  • a one-component diazotype material comprising paper having a fibrous side thereof sensitized by a lightsensitive composition containing, and in the absence of aniazo coupling component, an actively coupling lightsensitive diazo compound of the formula in which X is an anion, R is a radical selected from the group consisting of alkyl and aralkyl radicals and R is an aryl radical, and containing with said compound an aliphatic saturated dicarboxylic acid in which the carbon- 7.
  • a one-component diazotype material comprising paper having a fibrous side thereof sensitized by a lightsensitive composition containing, and in the absence of an azo coupling compound, an actively coupling lightsensitive diazo compound of the formula in which X is an anion, R is a radical selected from the group consisting of alkyl and aralkyl radicals and R is an aryl radical, and containing with said compound an aliphatic'saturated dicarboxylic acid in which the carboxylic acid radicals are linked with two carbon atoms forming part of a hydrocarbon radical having from 2 to 8 carbon atoms, the electrolytic dissociation constants of said acid being smaller than 2.3x 10*, said composition providing at least 1.7 millimols of said acid per square meter of the area of saidside, said composition also containing a xanthine.
  • a one-component diazotype material comprising paper having a'fibrous side thereof sensitized by a lightsensitivecomposition containing, and in the absence of an azo coupling component, an actively coupling light-sensitive diazo compound of the formula in which X is an anion, R is a radical selected from the group consisting of alkyl and aralkyl radicals, and Y is a radical selected from the group consisting of acylamino, arylmercapto, and aryl radicals, and containing with said compound an aliphatic saturated dicarboxylic acid in which the carboxylic acid radicals are linked with two carbon atoms forming part of a hydrocarbon radical having from 2 to 8 carbon atoms, the electrolytic dissociation constants of said acid being smaller than 2.3 X 10- said composition providing at least 1.7 millimols of said acid persquare meter of the area of said side, said composition also containing boric acid and an organic hydroxy compound capable of forming a complex with boric acid.
  • a one-component diazotype material comprising paper having a fibrous side thereof sensitized by a lightsensitive composition containing, and in the absence of an azo coupling component, an actively coupling lightsensitlve diazo compound of the formula in which X is an anion, R is a radical selected from the group consisting of alkyl and aralkyl radicals and R is an aryl radical, and containing with said compound an aliphatic saturated dicarboxylic acid in which the carboxylic acid radicals are linked with two carbon atoms forming part of a hydrocarbon radical having from 2 13 10.
  • a one-component diazotype material comprising paper having a fibrous side thereof sensitized by a lightsensitive composition containing, and in the absence of an azo coupling component, an. actively coupling lightsensitive diazo compound of the formula xm-QR,
  • R is a radical selected from the group consisting of alkyl and aralkyl radicals and R, is an aryl radical, and containing with said compound an aliphatic saturated dicarboxylic acid in which the carboxylic acid radicals are linked with .two carbon atoms forming part of a hydrocarbon radical having from 2 to 8 carbon atoms, the electrolytic dissociation constants of said acid being smaller than 2.3X10 said composition providing at least 1.7 millimols of said acid per square meter of the area of said side, said composition also containing boric acid and an organic hydroxy compound capable of forming a complex with boric acid.
  • a one-component diazotype material comprising paper having a fibrous side thereof sensitized by a lightsensitive composition containing, and in the absence of an azo coupling component, an actively coupling lightsensitive diazo compound of the formula KN,- Y
  • X is an anion
  • R is a radical selected from the group consisting of alkyl and aralkyl'radicals
  • Y is aradical selected from the group consisting of'acylamino, arylmercapto, and aryl radicals, and containing with said compound an aliphatic saturated dicarboxylic acid in which the carboxylic acid radicals are linked with two carbon atoms forming partof a hydrocarbon radical hav- 14 an azo coupling component, an actively coupling light sensitive diazo compound of the formula v :(N s-Ri in which X is an anion, R is a radical selected from the group consisting ofaikyl and aralkyl radicals and R is an aryl radical, and containing with said compound an aliphatic saturated dicarboxylic acid in which the "carboxylic acid radicals are linked with two carbon atoms forming part of a hydrocarbon radical having from 2 to 8 carbon atoms, the electrolytic dissociation constant
  • a one-component diazotype material comprising paper having a fibrous side thereof sensitized by a lightsensitive composition, containing, and in the absence of an azo coupling component, an actively couplingliightsensitive diam compound of the formula XN R1 a in which X is an anion, R is a radical selected from the .group consisting of alkyl and aralkyl radicals and R,
  • said composition also conis an aryl radical, and containing with said compound an aliphatic saturated dicarboxylic acid in which the carboxylic acid radicals are linked with two carbon atoms forming part of a hydrocarbon radical having from 2 to 8 carbon atoms, theelectrolytic dissociation constants of said acid being smaller than 2.3 X 10-, said composition providing at least 1.7 millimols of said acid per square taining a xanthine and boric acid and an organic hydroxy compound'capaible of forming a complex with boric acid.

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  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
US742025A 1957-06-17 1958-06-16 One-component diazotype material Expired - Lifetime US3016298A (en)

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3174860A (en) * 1959-02-26 1965-03-23 Azoplate Corp Light sensitive polymeric diazonium and azidoacrylamido reproduction material and process of making plates therewith
US3230087A (en) * 1959-02-26 1966-01-18 Azoplate Corp Light-sensitive polymeric diazonium and azidoacrylamido reproduction materials and process for making plates therefrom
US3338713A (en) * 1963-02-01 1967-08-29 Grinten Chem L V D Diazotype material
US3377165A (en) * 1964-01-22 1968-04-09 Minnesota Mining & Mfg Process of copying utilizing a blush lacquer coating and a photodecomposable progenitor of a plasticizer
US3382070A (en) * 1964-01-02 1968-05-07 Gen Aniline & Film Corp Black-line moist diazotype process
US3397985A (en) * 1964-06-01 1968-08-20 Oce Van Der Grinten Nv Light sensitive diazotype material and diazonium compounds therefor
US3480437A (en) * 1965-11-30 1969-11-25 Gaf Corp Two component diazo sensitizing compositions containing a xanthine compound
US3486900A (en) * 1965-06-02 1969-12-30 Keuffel & Esser Co Diazotype material
DE2325579A1 (de) * 1972-05-26 1973-12-13 Oce Van Der Grinten Nv Verfahren und vorrichtung zur herstellung von diazotypiekopien
US3944422A (en) * 1969-09-01 1976-03-16 Mita Industrial Company Limited Photosensitive material in use for diazo-type multicolor reproduction
US3970460A (en) * 1973-03-28 1976-07-20 Multitec Ag Diazotype composition
US4442195A (en) * 1981-07-15 1984-04-10 Konishiroku Photo Industry Co., Ltd. Photosensitive composition and article with o-quinone diazide and 6-membered cyclic acid-anhydride
JP3489739B2 (ja) 1998-07-29 2004-01-26 日本ビクター株式会社 Ｃｄ−ｒｏｍ読取器または同等物に適したクレジットカード型の情報媒体

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3386826A (en) * 1964-05-08 1968-06-04 Ibm Process for producing improved diazotype elements
NL6608011A (fr) * 1965-06-19 1966-12-20

Citations (3)

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US1870930A (en) * 1930-01-23 1932-08-09 Kalle & Co Ag Light-sensitive layer
GB415081A (en) * 1933-02-18 1934-08-16 Kalle & Co Ag Improvements in processes for the production of light sensitive layers by means of diazo compounds
US2405523A (en) * 1944-08-09 1946-08-06 Du Pont Light-sensitive photographic compositions and elements

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1870930A (en) * 1930-01-23 1932-08-09 Kalle & Co Ag Light-sensitive layer
GB415081A (en) * 1933-02-18 1934-08-16 Kalle & Co Ag Improvements in processes for the production of light sensitive layers by means of diazo compounds
US2405523A (en) * 1944-08-09 1946-08-06 Du Pont Light-sensitive photographic compositions and elements

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3230087A (en) * 1959-02-26 1966-01-18 Azoplate Corp Light-sensitive polymeric diazonium and azidoacrylamido reproduction materials and process for making plates therefrom
US3174860A (en) * 1959-02-26 1965-03-23 Azoplate Corp Light sensitive polymeric diazonium and azidoacrylamido reproduction material and process of making plates therewith
US3338713A (en) * 1963-02-01 1967-08-29 Grinten Chem L V D Diazotype material
US3382070A (en) * 1964-01-02 1968-05-07 Gen Aniline & Film Corp Black-line moist diazotype process
US3377165A (en) * 1964-01-22 1968-04-09 Minnesota Mining & Mfg Process of copying utilizing a blush lacquer coating and a photodecomposable progenitor of a plasticizer
US3397985A (en) * 1964-06-01 1968-08-20 Oce Van Der Grinten Nv Light sensitive diazotype material and diazonium compounds therefor
US3486900A (en) * 1965-06-02 1969-12-30 Keuffel & Esser Co Diazotype material
US3480437A (en) * 1965-11-30 1969-11-25 Gaf Corp Two component diazo sensitizing compositions containing a xanthine compound
US3944422A (en) * 1969-09-01 1976-03-16 Mita Industrial Company Limited Photosensitive material in use for diazo-type multicolor reproduction
DE2325579A1 (de) * 1972-05-26 1973-12-13 Oce Van Der Grinten Nv Verfahren und vorrichtung zur herstellung von diazotypiekopien
US3970460A (en) * 1973-03-28 1976-07-20 Multitec Ag Diazotype composition
US4442195A (en) * 1981-07-15 1984-04-10 Konishiroku Photo Industry Co., Ltd. Photosensitive composition and article with o-quinone diazide and 6-membered cyclic acid-anhydride
JP3489739B2 (ja) 1998-07-29 2004-01-26 日本ビクター株式会社 Ｃｄ−ｒｏｍ読取器または同等物に適したクレジットカード型の情報媒体

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GB895250A (en) 1962-05-02
GB895249A (en) 1962-05-02
NL107375C (fr)
NL218185A (fr)

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