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

• diazotype processes used for the-reproduction of documents two methods of development are used, the so-called dry development with gaseous ammonia and the so-called semi-wet development with alkaline solutions containing among other things the azo-dye coupling component or coupler. Consequently, there are also two types of light sensitivematerial suitable for the diazotype reproduction processes, namely, two component material for the dry development process and one component material for the wet development process. It is understood that the two essential components are the light sensitive diazo compound and the azo dye coupling component. In the case of the semi-wet materials, the azo dye coupling component is present in the developer but not in the light sensitive material. Principally, only four groups of the many classes of diazo compounds proposed for the wet development process have become of practical importance. These are the following:
• one-component diazotype material has been found which is admirably suited to the wet-development process. It includes a diazo compound which has a suitably high light sensitivity about twice as high as the types included under 1, 2 and 4 above as well as a suitably high coupling capacity and a relative low water solubility so it will not run or bleed in the developing solution.
• a diazo compound of the class of the present invention can be used to form the m'uchpreferred blackline. prints.
• diazo compounds of the present invention are those corresponding to one of the following general formulae:
• R represents an alkyl residue with straight or branched chain with, at least three carbon atoms and CH CH 0R O fir-C OR GHQ-CH2 HN N H:
• contrast of the copies produced with the papers according to the invention can be made even better by known additions to the light sensitive coating or by pretreatment of the paper with synthetic resin emulsions and/or finely divided silica or with casein and starch.
• Examples 1 Base paper of the kind commonly used for diazotype paper is coated with a solution containing in each liter of water 3 g. of gelatine g. of citric acid 5 g. of aluminum sulphate g. of glycol 10 cc. of alcohol g. of the zinc chloride double salt of the compound 4- diethylamino-2, S-di-n-butoxy-benzene-ldiazonium chloride and is then dried.
• the zinc chloride double salt of 4-diethyl-amino- 2, 5- di-n-butoxy-benzene-l-diazonium chloride is obtained as follows: I i
• Aminohydroquinone-di-n-butylether is twice directly ethylated with diethyl sulphate, consecutively, without solvent.
• the oily diethylamino-bydroquinone-di-n-butylether thus obtained boils at 182-l85 C. under 9 mm. of mercury.
• This base is coupled in glacial acetic acid.
• the dyestufi' produced is isolated and subjected to reduction with sodium carbonate and hydrosulphite.
• the 4- amino-2,5-di-n-butoxy-diethylaniline thus obtained is diazotised and can be satisfactorily isolated in the form of, for example, the zinc double salt.
• hydroquinone-di-n-butylether is nitrated in aqueous nitric acid.
• the nitro compound separates as a yellow oil, which is subjected to a vacuum distillation and which boils at a temperature of 208 to 209 C. at a pressure of a 12 mm. mercury.
• the corresponding amino compound is obtained, which boils in a vacuum at a temperature of 190 to 191 C. (9 mm. mercury).
• the dipropyl compound is coupled in glacial acetic acid with a suitable diazotized aromatic amine, e.g. diazotized sulphanilic acid, to give a dyestufi.
• a suitable diazotized aromatic amine e.g. diazotized sulphanilic acid
• the oily diazo compound is dissolved in water and separated by means of zinc chloride as a crystalline yellow zinc chloride double salt.
• chloronitro hydroquinone di n-butylether is heated for 5 hours with an excess of dimethylamine to a temperature of C. in an autoclave.
• the reaction product is transformed into the corresponding hydrochloride, reconverted into the free base and finally recrystallized from alcohol.
• the purified reaction product melts at a temperature of 63 to 64 C.
• the nitro group is catalytically reduced in an autoclave and an oily base (boiling point 202 to 204 C. at 9 mm. mercury) is obtained.
• This base is diazotized in a solution of hydrochloric acid and by adding zinc chloride, the zinc chloride double salt is separated as a yellow powder.
• the diazo compound containing two butoxy groups instead of the two propoxy groups in the 2,5 positions can be used with equally good results for the preparation of the one-component coating.
• 4 morpholino 2,5 di-n-butoxy-benzene-l-diazonium chloride can be prepared in analogous manner.
• the nitro component obtainable from the chlorhydroquinonedi-n-butylether by nitration with aqueous nitric acid melts at 8l-82 C.
• the morpholine ring is introduced by simple heating of the chlornitro-hydroquinone-di-n-butylether with the base.
• the melting point of the 4-nitro-2,5-di-n-butoxyphenyl morpholine is about 101-102" C. Reduction and diazotisation follow.
• the chloronitro-hydroquinone-di n propyl ether is boiled for several hours with aqueous piperidine until the reaction is quantitatively complete (about 10 hours).
• the 4-nitro-2,5- di-n-propoxyphenyl-piperidine which had been separated by diluting the reaction mixture with water, melts at a temperature of 80 to 81 C.
• the compound is reduced in hydrochloric acid to which a small quantity of ethyl alcohol has been added by means oi'zinc dust.
• the diazotisation takes place in aknown manner and results the crystallization of beautiful crystals of the zinc chloride double salt of the diazo compound.
• the 4-nitro-2,5-di-(isoamyloxy-phenyl)-morpholine that crystallizes out is isolated, reduced and diazotised.
• This compound is preferably precipitated in the form of the hydrochloride because the zinc salt is insufiiciently soluble.
• either of the homologous diazo compounds may be used, which in the 2,5 positions contain two isobutoxy groups or two isopropoxy groups, respectively, instead of the two isoamyloxy groups. Both compounds are prepared analogously to the preparation of the isoamyl compound described above.
• R is alkyl containing 3 to 5 carbon atoms
• R and R are alkyl groups containing 1 to 3 carbon atoms
• V c is a saturated heterocyclic group selected from the group consisting of morpholinyl and piperidyl.
• a light sensitive diazotype material of the single component type comprising a base material coated with a. light sensitive composition including a light sensitive diazo compound formed from a p-phenylene diamine of the general formula:
• R is alkyl containing 3 to 5 carbon atoms
• I l o is a saturated heterocyclic group selected from the group consisting of morpholinyl and piperidyl.
• a light-sensitive one component diazotype material comprising a base material coated with a light'sensitive composition including a light-sensitive diazo compound which is the product of diazotization of a compound of the formula where is a saturated heterocyclic group selected from the group consisting of morpholinyl and piperidyl.
• a light sensitive diazotype material of the single component type comprising a base material coated with a. light sensitive composition including a light sensitive diazo compound formed from a p-phenylenediamine of the general formula:
• a light sensitive diazotype material of the single component type comprising a base material coated with a light sensitive composition including a light sensitive diazo compound of 4-morpholine-2,5-di-iso-butoXy-benzene-l-amine.
• a light sensitive diazotype material of the single component type comprising a base material coated with a light sensitive composition including a light sensitive diazo compound of 4-morpholine-2,S-di-iso-propoxybenzene-l-amine.
• a light sensitive diazotype material of the single component type comprising a base material coated with a light sensitive composition including a light sensitive diazo compound of 4-piperidino-Z,S-di-n-butoxy-benzenel-amine.
• a light sensitive diazotype material of the single component type comprising a base material coated with a light sensitive composition including a light sensitive cliazo compound of 4-dimethylamino 2,5-di-n-butoxybenzene-l-amine.

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• Chemical & Material Sciences (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
• Heat Sensitive Colour Forming Recording (AREA)

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  • NL NL235161D patent/NL235161A/xx unknown
  • NO NO98358D patent/NO98358A/no unknown
  • NL NL113082D patent/NL113082C/xx active
  • BE BE574785D patent/BE574785A/xx unknown
  • IT IT601676D patent/IT601676A/it unknown
• 1958
  • 1958-01-18 DE DEK33853A patent/DE1086123B/de active Pending
• 1959
  • 1959-01-12 GB GB1114/59A patent/GB853020A/en not_active Expired
  • 1959-01-13 CH CH6827259A patent/CH373956A/de unknown
  • 1959-01-15 FR FR784068A patent/FR1220984A/fr not_active Expired
  • 1959-01-15 US US786920A patent/US3028240A/en not_active Expired - Lifetime

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