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
  • G03C1/54—Diazonium salts or diazo anhydrides

Definitions

• the essential suitability of the p-aminobenzenediazo compounds concerned for the preparation of so-called two-component material for the dry-development process, or of socalled one-component material for the semi-wet development process, is determined in each case by the nature of the substituents which may be adhering directly to the benzene ring or to the nitrogen of the tertiary amino group.
• those sensitising mixtures are well suited which contain p-aminobenzenediazo compounds with a tertiary amino group which are substituted on the tertiary nitrogen atom by an aralkyl radical, for example (and preferably) the benzyl radical.
• an aralkyl radical for example (and preferably) the benzyl radical.
• the colour deepening which shows in photocopies prepared from one-component material sensitised with such diazo compounds is also attributable to the presence of the aralkyl group in the tertiary aminobenzenediazo compound.
• material sensitized with l-N-(benzylethyl)-amino-4-di azobenzene is therefore used which, after exposure under the original, is treated with developer which is soluble in alkalis and contains phloroglucinol.
• the objects of the invention are to provide improved diazotype material and to provide improved sensitising compositions suitable for the preparation of diazotype material which are free from the disadvantages explained above.
• diazotype material which comprises, as light-sensitive component, a diazo compound having the general formula:
• R is a hydroxyalkyl radical containing 2 to 4 carbon atoms
• R is an aryloxyalkyl or aryl thioalkyl radical in which the aromatic component may also be substituted;
• R is a hydrogen atom or an alkyl or alkoxy or betahydroxyalkoxy group
• R is a hydrogen or halogen atom or an alkyl or alkoxy group; and X is an acid anion.
• the hydroxyalkyl radical adhering on the nitrogen of the amino group is characteristic.
• the sensitising mixtures according to the invention therefore permit the addition of stabilisers in such large amounts that the shelf life of the one-component material sensitised with them is excellent, even under tropical conditions.
• a further substantial advance based on the invention is to be seen in the fact that the dyes which are formed on the photocopies prepared from the diazotype material prepared with the sensitising mixtures according to the invention are substantially more insensitive to changes in pH-value and therefore have a much lesser tendency to change of colour.
• the photocopies which are prepared with the use of the one-component material prepared with the sensitising mixtures according to the invention can be developed with alkaline solutions or, if the benzene nucleus of the diazo compound according to the invention which is present as lightsensitive substance bears substituents which accelerate coupling, also with a neutral or acid solution.
• the coating supports on which the light-sensitive coating is formed with the sensitising mixtures according to the invention are the 3 ;supports with a hydrophilic surface which are commonly .used in diazotype processes.
• diazo compounds according to the above general formula which characterise the sensitising mixtures according to the invention are new. They are obtained according to known methods. In the table, the formulae of some representatives of these compounds are set forth as examples. Their preparation is described below.
• the sulphate tends to split hydrolytically in the presence of water.
• the press cake is dissolved in about 1 litre of methanol (yellowish-red solution) and the solution rendered neutral with about caustic soda solution, with good stirring. Filtering with suction is effected from the precipitated salt, the salt is washed with a little methanol and Raney nickel is added to the weakly alkaline solution (pH 8). Reduction proceeds at between 20 and 40 C.
• the initially colourless amine solution is freed from nickel and to the 1-N-(beta-hydroxyethyl-beta-phenoxyethyl)- amino-2-methoxy-4-amino-S-chlorobenzene there are immediately added 150 ccm.
• nitric acid 1.52 are added dropwise at room temperature. The temperature rises to 32 C.
• the nitro compound sulphuric acid salt
• the free base is obtained by treatment with n-solution of caustic soda.
• the nitro compound is now reduced catalytically with Raney nickel in methanolic solution. After reduction the solution, which contains oxidisable l-N-(beta-hydroxyethylbeta-phenoxyethyl)-amino-2-ethoxy-4-amino 5 chlorobenzene, is filtered off from the nickel and 150 ccm.
• the diazo compound from l-N-(beta-hydroxyethyl-beta-phenoxyethyl)- amino-2-hydroxyethoxy-4-amino-5 chlorobenzene forms yellow crystals, which are filtered with suction and, for purification, recrystallised from about 200 ccm. of water at 60 C. Yield: 10 g. Melting point: 107l08 C., with decomposition.
• the yellow diazo solution obtained is filtered over animal charcoal and the diazo compound precipitated out of the solution by the addition of 10 ccm. of 50% solution of stannic chloride and 50 g. of sodium chloride.
• the diazo compound is then filtered with suction and, for purification, dissolved in water and reprecipitated by adding sodium chloride. Yield: 10 g., melting point 9092 C., with decomposition.
• the solvent is evaporated from it and the l-N-(beta-hydroxyethyl-betanaphthoxyethyl)-amino-2-methoXy-4-amino chlorobenzene which remains behind is, as crude product, absorbed in 300 ccm. of 16% hydrocloric acid and diazotised by adding dropwise 20 ccm. of 2 N solution of sodium nitrite.
• diazo compound precipitates out of the yellow solution as zinc chloride double salt, which is purified by dissolving it in 700 ccm. of water and precipitating it with sodium chloride. Melting point: 100- 120 C., with decomposition.
• the diazo compounds of the present invention may be used in the normal manner as diazo components of diazotype compositions and diazotype material prepared therewith. Numerous available azo coupler components may be used to prepare developer solutions normally employed with one-component diazotype materials. The following examples set forth a few embodiments of the present invention.
• EXAMPLE 2 Transparent paper is coated with an aqueous solution which for each 90 ccm. of water contains:
• Citric acid g 0.5 Sodium 1,3,6--naphthalenetrisulphonate g 3.5 Fluoboric acid salt of the diazo compound from 1 N (beta hydroxyethyl beta phenoxyethyl)- amino 2 methoxy 4 aminobenzene (Formula IV) g 3.2 Triglycol ccm 2.5 Isopropanol ccm 5.0
• EXAMPLE 3 White photocopying base paper with a precoat consisting of colloidal silicic acid and polyvinyl acetate is coated with an aqueous solution which in 95 ccm. of water contains:
• EXAMPLE 4 White photocopying base paper, which is provided with a precoat consisting of colloidal silicic acid and polyvinyl acetate, is coated with an aqueous solution which for each com. of water contains:
• EXAMPLE 5 White photocopying base paper as used in Example 4 with a precoat of colloidal silicic acid and polyvinyl acetate is coated with an aqueous solution which contains for each 95 ccm, of water:
• EXAMPLE 6 White photocopying base paper, which is provided with a precoat consisting of colloidal silicic acid and polyvinyl acetate, is coated with an aqueous solution which for each 95 ccm. of water contains:
• Diazotype material comprising a support and a light-Sensitive composition thereon comprising a lightsensitive diazonium component having the general formula:
• R is a hydroxyalkyl of 2 or 3 carbon atoms
• R is an aryloxalkyl or arylthioalkyl wherein the alkyl contains 2 or 3 carbon atoms;
• R is hydrogen, methyl, methoxy, ethoxy, or beta-hydroxy-ethoxy
• R is hydrogen, chlorine, or ethoxy
• X is an anion of an acid.
• diazo component is 2 chloro 4 (N f3 hydroxyethyl-N-fiphenylthioethyl) amino 5 methoxy benzenediazonium-chloride- SnCl 8. Material according to claim 1 wherein said diazo component is 2 chloro 4 (N-B-hydroxyethyl-N-B- naphthoxyethyl) amino 5 methoxy benzene diazonium-chloride ZnCl 2.
• diazo component is 2 chloro 4 (N-fi-hydroxyethyl-N-yphenoxypropyl) amino S-methoxy-benzene-diazoniumborofluoride.
• said diazo component is 4-(N-fl-hydroxypropyl-N-fi-phenoxyethyl)- amino-benzene-diazonium-chloride-SnCl 11. Material according to claim 1 wherein said diazo component is 2 chloro 4-(N-fl-hydroxyethyl-N-fi-4'- chloro phenoxyethyl) amino 5 methoxy-benzenediazonium-chloride SnCl 12. Material according to claim 1 wherein said diazo component is 3 methyl-4-(N-fi-hydroxyethyl-N-fi-phenoxyethyl) amino-benzene-diazonium-chloride-CdCl 2.
• R is a hydroxyalkyl of 2 or 3 carbon atoms
• R is an aryloxyalkyl or arylthioalkyl wherein the alkyl contains 2 or 3 carbon atoms;
• R is hydrogen, methyl, methoxy, ethoxy, or beta-hydroxy-ethoxy
• R is hydrogen, chlorine, or ethoxy
• X is an anion of an acid.
• R is beta-hydroxyethyl
• R is beta-phenoxyethyl or gamma-phenoxypropyl
• R is methoxy or ethoxy
• R is H or Cl
• X is the anion of fluoboric acid or the chloride ion in double salt combination with stannic chloride.

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• Chemical & Material Sciences (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
• Heat Sensitive Colour Forming Recording (AREA)

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Citations (5)

• 1965
  • 1965-05-08 DE DE19651693196 patent/DE1693196B2/de active Granted
• 1966
  • 1966-05-05 DK DK232066AA patent/DK111472B/da unknown
  • 1966-05-05 AT AT427466A patent/AT276082B/de active
  • 1966-05-05 US US547799A patent/US3498790A/en not_active Expired - Lifetime
  • 1966-05-06 CH CH661566A patent/CH475577A/de not_active IP Right Cessation
  • 1966-05-06 FR FR60504A patent/FR1478912A/fr not_active Expired
  • 1966-05-06 BE BE680702D patent/BE680702A/xx unknown
  • 1966-05-06 FI FI661198A patent/FI44873C/fi active
  • 1966-05-06 SE SE06296/66A patent/SE326370B/xx unknown
  • 1966-05-06 GB GB20203/66A patent/GB1084487A/en not_active Expired
  • 1966-05-06 NL NL6606213A patent/NL6606213A/xx unknown
  • 1966-05-06 ES ES0326442A patent/ES326442A1/es not_active Expired

Patent Citations (5)

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