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

• Particularly suitable for one-component diazotype layers are 4-dialkylamino-3-(chloroor bromo-) phenoxy-Z-chlm robenzene diazonium compounds in which the alkyl groups contain at most four C atoms; materials made with these develop rapidly with weakly acid bufiered phloroglucinol solutions, yielding black images on bright white or foggy gray backgrounds.
• the diazotype material may be so-called one-component diazotype material which is developed with a liquid containing an azo-coupling component, so-called two-component diazotype material which is developed with the aid of ammonia vapour, or heat-developable diazotype material.
• diazonium compounds for sensitizing diazotype material should, as a rule, have a number of other properties. A very important one of these is that the photo-decomposition should form products which are completely or almost completely colourless, which when exposed to light show little or no staining and which do not actively react with diazonium compounds to yield dyestuffs.
• diazonium compounds of very high light-sensitivity have come into use for sensitizing diazotype materials.
• These compounds are chiefly benzene diazonium compounds having a tertiary amino group in the para-position with respect to the diazonium group and an etherified hydroxyl group in the meta-position, and possibly a further substituent, such as alkoxy, alkyl or halogen, in the para-position with respect to the etherified hydroxyl group.
• benzene diazonium compounds having a tertiary amino group in the para-position with respect to the diazonium group and an etherified hydroxyl group in the meta-position, and possibly a further substituent, such as alkoxy, alkyl or halogen, in the para-position with respect to the etherified hydroxyl group.
• diazonium compounds are also very light-sensitive; however, they have a higher coupling activity than the corresponding compounds with an alkoxy group in meta-position with respect to the diazonium group, and consequently are better suitable for application in onecomponent diazotype material which is developed with weakly acid buffered phloroglucinol developers.
• One-component diazotype material sensitized with a diazonium compound according to general Formula I yields copies which present a somewhat stained completely exposed background and show a not-negligible yellowing when exposed for a considerable time to daylight or to the light of high-pressure mercury vapour lamps.
• the invention relates to diazonium compounds of a new type and to diazotype material manufactured with the aid of these compounds, which material avoids or minimizes the disadvantages described above with respect to the known materials.
• diazonium compounds of general Formula II in which X is an anion and Y is a halogen atom, R represents a substituted or non-substituted aryl group, R represents a substituted or non-substituted alkyl, branched alkyl or aralkyl group, and R represents a substituted or nonsubstituted alkyl, branched alkyl, cycloalkyl or aralkyl group.
• the diazonium compounds according to the invention are very light-sensitive and yield both light-coloured and dark azo-dyestutfs with the azo-coupling components commonly used in the diazotype process. They couple more actively, bleach out more clearly, and form less reactive photo-decomposition products than the diazonium compounds according to general Formula I.
• Diazotype materials sensitized with diazonium compounds according to the invention have a higher developing speed and yield copies which have a clearer completely exposed background and show less yellowing than corresponding diazotype material sensitized with a diazonium compound according to general Formula I.
• the diazotype material according to the invention is preferably one-component diazotype material.
• diazonium salts e.g. as diazonium chloride, sulfate, or metal chloride double salt, such as chlorozincate, chloromanganate and chlorostannate, as diazonium borofiuoride or diazonium aryl sulfonate.
• diazotype materials can be applied in diazotype material individually, mixed together, or in admixture with diazonium compounds of other types. It goes without saying that a diazotype material according to the invention, accordingly as it contains a higher content of another diazonium compound, will present the specific advantages of the diazonium compounds according to the invention to a less degree.
• the familiar supports such as paper, tracing paper, printing-plate paper, tracing linen, opaque linen, synthetic paper, metal sheets, glass fibre, polyester film and the like can be sensitized.
• the diazonium compound may or may not be incorporated in a hydrophilic or hydrophobic film layer.
• Preferred diazonium compounds according to the invention are those carrying a chlorine or a bromine atom in the ortho-position with respect to the diazonium group, a phenoxy group substituted with one or more halogen atoms in the meta-position, and in the para-position a dialkylamino group the substituted or non-substituted alkyl groups of which each carry at most 4 C-atoms.
• diazotype material sensitized with these diazonium compounds furnishes copies in azo-dyestutfs which in the diazotype process are called neutral black.
• the developing speed of such diazotype material is higher than that of diazotype materials sensitized with the corresponding diazonium compounds of general Formula I.
• the completely exposed background of the copies is bright white; and shows-only little yellowing when exposed to daylight or to the light of a high-pressure mercury vapour lamp; the so-called foggy background of the copies is a fine neutral grey.
• the conventional auxiliary agents can be used, e.g. acids, such as citric acid, tartaric acid and boric acid; stabilizers, such as benzene and naphthalene sulfonic acids, p-phenolsulfonic acid, and their water-soluble salts; metal salts, such as zinc chloride, magnesium chloride, nickel sulfate and alum; materials which serve to improve the developing speed, such as glycerol, polyethylene glycol, urea, thiosinamine and the like; surface-improving substances, such as finely divided silicon dioxide (colloidal or non-colloidal), aluminum oxide, barium sulfate and rice starch; binders, such as gelatin, gum arabic, cellulose ethers, starch derivatives, polyvinyl alcohol; dispersions of synthetic resins, such as dispersions of cationic, non-ionic, and anionic polyvinyl acetate; substances which serve to stabilize the background of
• the phloroglucinol developers which are used in the one-component diazotype process often vary as to their composition and acidity. Below, two weakly acid phloroglucinol developers are described which are employed in practice and are used for development in a number of the following examples.
• Developer A is a solution of:
• Phloroglucinol g 4 Acetoacetanilide g 0.1 2-ethylhexyl sulfate ml 3 Beet sugar g 15 Benzoic acid g 2.5 Sodium benzoate g 14 Sodium formate g-- 135 in 1000 ml. of water.
• the pH of this liquid is approximately 5.8.
• Developer B is a solution of:
• Phloroglucinol 6.5 Resorcinol 4 Thiourea 10 Sodium dibutylnaphthalene sulfonate 2 Sodium formate 14 Sodium benzoate 22 Trisodium citrate (2 aq.) 49 Citric acid 1.2
• the pH of this liquid is approximately 6.5.
• EXAMPLE I A sheet of white base paper for the diazotype process, of weight g./m. is sensitized with a liquid containing:
• diazoty-pe papers are very light-sensitive.
• Diazotype paper A develops somewhat more rapidly than diazotype paper B.
• a strip of each sheet is imagewise exposed underneath a transparent ink drawing until the diazonium compound underneath the image-free portions of the drawing has completely bleached out, and then both are developed with developer B.
• the copies thus obtained show a black image on a white background.
• the background of copy A is whiter than that of copy B, and moreover it shows less yellowing when the copies are exposed to daylight or to the light of a high-pressure mercury vapour lamp.
• the diazonium compound according to the invention used in this example was prepared as follows:
• EXAMPLE II White base paper for the diazotype process, of weight 80 g./m. is sensitized with a solution containing 4-di('-acetoxyethyl amino-3-(4'-chlorophenoxy)-2- chlorobenzene diazonium chloride, zinc chloride in 1000 ml. of water and dried.
• a sheet of the diazotype paper thus obtained is imagewise exposed underneath a transparent ink drawing until the diazonium compound underneath the image-free portions of the drawing has completely bleached out, and is then developed with developer A.
• the copy shows a violet-black image on a bright white background.
• the diazotype paper thus obtained develops somewhat more slowly, bleaches out with a somewhat more pronounced stain, and gives copies which show stronger yellowing when exposed to daylight.
• the diazonium compound used in this example was prepared as follows:
• the nitro group of 3-chloro-2-(4-chlorophenoxy) nitrobenzene was reduced to an amino group, which was converted with epoxyethane into a di-(2-hydroxyethyl) amino group, from which a di(2'-acetoxyethyl)amino group was obtained with the aid of acetic anhydride.
• the product thus prepared was nitrated.
• the diazonium salt was prepared in the usual way by reduction and diazotization.
• the plate After the development, the plate is sponged off with water. It shows a white image on a yellow background.
• the plate is placed in an olfset printer. At least 100 good positive offsetprints can be made from it.
• the diazonium compound used in this example was prepared as follows:
• 3-chloro-2-(4'-chlorophenoxy)aniline was tosylated, nitrated, and methylated. After saponification of the tosylamino group the 4 nitro-3-chloro-2-(4'-chlorophenoxy)- N-methylaniline obtained was benzylated. From the 4- nitro-3-chloro 2 (4' chlorophenoxy) N methyl N- benzylaniline, the diazonium salt was obtained in the usual way by reduction and diazotization.
• X is an anion
• Y is a halogen atom
• R is a non-substituted or lower alkylor halogensubstituted phenyl group
• R is a lower alkyl, lower branched alkyl or benzyl group
• R is a lower alkyl, lower branched alkyl, cyclohexyl or benzyl group.
• R is a halogen-substituted phenyl group and each of R and R is an alkyl group having at most 4 C atoms.
• a diazonium compound according to claim 1 namely, a 4 dialkylamino 3 chlorophenoxy-Z-chlorobenzene diazonium compound.
• a diazonium compound according to claim 1 namely, a 4 N alkyl-N-benzylamino 3 chlorophenoxy- 2-chlorobenzene diazonium compound.
• a diazonium compound according to claim 1 namely, a 4 N benzyl-N-cyclohexylamino 3 cyclophenoxy- 2-chl0robenzene diazonium compound.
• a diazonium compound according to claim 1 namely, a 4 dimethylamino 3 chlorophenoxy-Z-chlorobenzene diazonium compound.
• a diazonium compound according to claim 1 namely, a 4 N methyl-N-benzylamino-3-chlorophenoxy- 2-chlorobenzene diazonium compound.
• a diazotype material comprising a support carrying a light-sensitive layer containing a diazonium compound as defined in claim 1.
• a one-component diazotype material comprising a support carrying a light-sensitive layer containing, in the 7 8 substantial absence of an azo coupling component, a NORMAN G. TORCHIN, Primary Examiner. diazonium compound as defined in claim 2.
• Q BOWERS Assistant Examiner References Cited Us CL X FOREIGN PATENTS 5 260-141, 142; 96-49, 75, 33

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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)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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Citations (2)

• 0
  • NL NL130247D patent/NL130247C/xx active
• 1965
  • 1965-03-12 NL NL6503184A patent/NL6503184A/xx unknown
• 1966
  • 1966-03-10 DE DE1693191A patent/DE1693191B2/de not_active Withdrawn
  • 1966-03-10 US US533257A patent/US3442650A/en not_active Expired - Lifetime
  • 1966-03-10 SE SE03177/66A patent/SE334163B/xx unknown
  • 1966-03-11 GB GB10831/66A patent/GB1081274A/en not_active Expired

Patent Citations (2)

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