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
  • G03C1/58—Coupling substances therefor

Definitions

• R3 S CH3] 1 l Rj N+Ri X- represents an anion and may be missing When the anion is present in the R group,
• R represents an organic group introduced by quaternization, each of R and R represents an alkyl group or an aryl group and only one of R and R is hydrogen; and recording materials useful therein.
• a preferred thiazolium compound is 2,3-dimethyl-thiazolium ethyltolusulphonate and a preferred diazoniurn compound is p-diethylaminobenzene-diazonium tetraborofluoride.
• This invention relates to recording and reproduction of information and to the use of particular chemical compounds in the diazo recording process.
• diazo recording process is based on the fact that certain diazo compounds, eg diazonium salts, can be decomposed information-wise by light under nitrogen evolution and remaining diazo compound can react with a so-called coupler to form a dye.
• diazo compounds eg diazonium salts
• the recording material contains a diazo compound and a coupler.
• it contains an acid that prevents the premature reaction of the diazo compound and the coupler.
• a volatile base such as ammonia. This neutralizes the acid and allows the remaining diazo compound to combine with the coupler and to form a dye in the image areas.
• the recording material contains only the diazo compound. After the recording material is exposed image-wise to ultra-violet, it is treated with an alkaline solution containing the coupler. The remaining diazo compound couples with the coupler in the nonexposed areas.
• a coupler in the broader definition is a substance that bears an active or mobile hydrogen atom.
• Normally used couplers are aromatic hydroxy compounds such as phenols and naphthols of which 2,3-dihydroxynaphthalene-6-sulphonic acid is a typical example.
• Couplers contain a reactive methyl, or methylene group as described in the Belgian patent specification 459,543 filed Aug. 3, 1945 by Gevaert Photo- Production N.V. and United States patent specification 2,532,744 of James M. Straley, issued Dec. 5, 1950.
• Typical examples of the latter class are quaternary salts of 2- methylquinoline, 2-methyl thiazole and 2-methyl-benzothiazole and N-methyl-2-methylene-benzothiazoline.
• active methyl couplers represented by the following general structure can be used to produce diazotype materials with good shelf life and still high coupling speed for the formation of green to violet dyes;
• s CHa X- represents an anion eg, a chloride, bromide, iodide, perchlorate, thiocyanate, benzene sulphonate, p-toluene sulphonate, methyl sulphate, ethyl sulphate or a propyl sulphate anion, but X- is missing when the anion is already contained in the R group (betaine salt form), e.g.
• R represents an organic group introduced by quaternization, e.g. an aliphatic group, including a cycloaliphatic group, a saturated aliphatic group, an unsaturated aliphatic group or one of said groups in substituted form, e.g. an alkyl groups, more particularly a C -C alkyl group, an allyl group, a cycloalkyl group, e.g. a cyclopentyl or cyclohexyl group, a substituted cycloalkyl group, a substituted alkyl group, e.g.
• a hydroxyalkyl group a carboxyalkyl group, a sulphoalkyl group, a sulphatoalkyl group, a phosphoalkyl group, a phosphoester substituted alkyl group, an acetoxyalkyl group, wherein the substituted alkyl group preferably contains from 1 to 4 carbon atoms, such as in fi-hydroxyethyl, B-acetoxyethyl, sulphopropyl, sulphobutyl, phosphopropyl, sulphato propyl, and sulphato butyl, further the substituted alkyl group wherein M is hydrogen, an onium group or a metal atom, B represents a lower alkylene group such as a methylene, ethylene, propylene or butylene group, and A represents a methylene group or group, (examples of such substituted alkyl group are described in the United Kingdom patent specification 886,271 filed June 20, 1957 by Geva
• A represents a lower alkylene group such as a methylene, ethylene, propylene or butylene group
• B represents an alkyl group, an amino group, a substituted amino group and also a hydrogen atom in the case V is a single bond
• W and V each represent a --CO-radical, a SO radical or a single bond but at least one of them is a -SO radical, (examples of such substituted alkyl groups are described in the United Kingdom patent specification 904,332 filed July 5, 1957 by Gevaert Photo-Producten N.V., e.g.
• a substituted alkyl group e.g. a C -C alkyl group preferably a methyl group, an ethyl group or a chloromethyl group
• an aryl group including a substituted aryl group e.g. a phenyl group, a biphenyl group or a methoxyphenyl group
• Thiazolium compounds are known as starting materials for the preparation of methine dyes suited for the spectral sensitization of photographic silver halide emulsions. References to the preparation of preferred thiazolium compounds are given in conjunction with Table 2 further on.
• the thiazolium compounds are allowed to couple with diazo compounds.
• diazo compounds are diazonium salts that can optionally be produced from diazo sulphonates.
• the diazonium salts suitable for use according to the present invention can be defined as aromatic compounds bearing a diazo group, of which one valency is satisfied by a carbon atom from the aromatic nucleus and the other valency by an acidic ion.
• Particularly suitable diazonium compounds are the stabilized diazonium salts, preferably the zinc chloride double salts and fluoroborates.
• Exemplary diazonium salts are those prepared by diazotization of amines listed in Table 1.
• Couplers No. 1 and 2 can be prepared according to a method described in the French patent specification 757,- 768 filed June 29, 1933 by Eastman Kodak.
• Couplers No. 3 and 4 can be prepared according to methods described in the German patent specification 908,346 filed June 6, 1942 by Gevaert 'Photo-Producten NV. and the French patent specification 739,314 filed June 30, 1932 by Eastman Kodak, respectively.
• Coupler No. 5 can be prepared according to E. D. Sych, Ukrain. Khim. Zhur. 22, 80 (1956).
• Coupler No. 7 can be prepared according to T. Takahashi & M. Hayami, Yakagaku Zasshi, 81, 1419 (1961).
• Coupler No. 6 can be prepared analogously to compound 7.
• Coupler No. 8 can be prepared according to J. L. B. Smith, J. Chem. Soc. 1923, 2288.
• Coupler No. 9 can be prepared according to Belgian patent specification 652,320 filed Aug. 26, 1964 by DuPont de Nemours.
• Couplers No. 12 and 13 can be prepared according to US. patent specification 2,148,441 of G. A. Dawson and E. B. Middleton, issued Feb. 28, 1939.
• Coupler No. 14 can be prepared according to E. D. Sych, Ukrain. Khim. Zhur. 22, 217 (1956) 27, '83 (1961).
• Suitable supports or layers used in copying materials according to the present invention have liquid-absorbing characteristics, as e.g., ordinary Wood pulp paper or rag type paper but also textiles including fabrics made of cotton, cellulose acetate, regenerated cellulose, in other words all types of Woven or felted materials, which can be impregnated with a solution containing one or more of the diazonium compounds and/ or couplers may be used.
• a transparent sheet is used as support, e.g. a Water-impermeable resin sheet.
• a transparent sheet is used as support, e.g. a Water-impermeable resin sheet.
• the imaging chemicals are preferably applied into a hydrophilic colloid layer e.g., a gelatiu-containing layer.
• the radiation sensitive coating composition containing a diazonium compound may contain all kinds of other ingredients, e.g. wetting agents, substances generating a base on heating or a material releasing base on heating, e.g. urea and the substances used for that purpose described, e.g., in the United Kingdom patent specification 983,363 filed May 8, 1961 by Nashua Corp. and the French patent specifications 1,376,708 and 1,376,709 both filed Sept. 17, 1963 by Et. Bauchet et Co., further optical brightening agents, pigments, e.g. silica, and antioxidants improving the whiteness of the areas, in which the diazonium compound has been destroyed. Suitable antioxidants are thiourea, ascorbic acid and allyl isothiocyanate in concentrations ranging from 15 to 25 percent by Weight in respect of the diazonium salts.
• other ingredients e.g. wetting agents, substances generating a base on heating or a material releasing base on heating, e.g.
• Preferred amounts of diazonium compound and coupler per sq. m. are in the range of 0.1 g. to 0.5 g. and 0.1 g. to 1.5 g. respectively.
• a good storage stability of a coating composition containing a diazonium compound and a coupler according to the general formula can be obtained by using in admixture with said compounds an acid, e.g. citric acid, tartaric acid, boric acid, trichloroacetic acid, tribromoacetic acid, sulphosalicylic acid, phosphoric acid or 1,3,6-naphthalenetrisulphonic acid disodium salt in an amount of 100 to 200 percent by weight in respect of the diazonium salt.
• an acid e.g. citric acid, tartaric acid, boric acid, trichloroacetic acid, tribromoacetic acid, sulphosalicylic acid, phosphoric acid or 1,3,6-naphthalenetrisulphonic acid disodium salt.
• EXAMPLE 1 A coating composition was prepared by mixing the following ingredients until dissolution of the Water-soluble compounds:
• citric acid40 g citric acid40 g.
• colloidal silica-1 g colloidal silica-1 g.
• the composition was coated onto a white paper base in a proportion of 19 g. per sq. m. and after drying through a line diapositive exposed with ultraviolet light in a common diazotype copying apparatus.
• the development proceeded by leading the exposed material through ammonia vapour.
• EXAMPLE 2 A photographic cellulose triacetate base provided with a subbing layer on the basis of gelatin was coated with the following composition: diazo 6910 g. 10% by weight aqueous solution of perchloric acid 75 ml. 2,3-dimethyl-thiazolium ethyl-tolusulphonate-IO g. saponine-0.5 g. n-propanol-IOO ml. 0.5% by weight aqueous gelatin solution-320 ml.
• a method for recording and reproducing information which comprises the steps of decomposing informationwise a diazo compound and allowing to react remaining diazo compound with a thiazolium compound corresponding to the following general formula:
• X represents an anion, but is missing when the anion is already contained in the R group
• R represents an organic group introduced by quaternization, each of R and R represents hydrogen, an alkyl group including a substituted alkyl group, or an aryl group including a substituted aryl group, the thiazolium nucleus being free from hydrogen in the 5-position when in the 4-position R is hydrogen and vice-versa.
• diazonium salt is of the Zinc chloride double salt or fluoroborate type.
• X- represents an anion, but is missing when the anion is already contained in the R group
• R represents an aliphatic group including a cycloaliphatic group, a saturated aliphatic group, an unsaturated aliphatic group or one of said groups in substituted form,
• each of R and R represents hydrogen, an alkyl group including a substituted alkyl group, or an aryl group including a substituted aryl group, the thiazolium nucleus being free from hydrogen in the 5-position when in the 4-position R is hydrogen and vice-versa.
• a diazotype recording material wherein the diazo compound has been prepared by diazotization of a primary aromatic amine, which in paraposition with respect to the primary amino group contains a tertiary amino group.

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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)
• Thiazole And Isothizaole Compounds (AREA)

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• 0
  • BE BE760061D patent/BE760061A/nl unknown
• 1969
  • 1969-12-30 GB GB6332669A patent/GB1324082A/en not_active Expired
• 1970
  • 1970-11-17 CA CA098352A patent/CA920579A/en not_active Expired
  • 1970-12-02 US US94606A patent/US3676133A/en not_active Expired - Lifetime
  • 1970-12-07 JP JP45108409A patent/JPS498891B1/ja active Pending
  • 1970-12-07 FR FR7044003A patent/FR2073028A5/fr not_active Expired
  • 1970-12-12 DE DE19702061238 patent/DE2061238A1/de active Pending
  • 1970-12-15 NL NL7018258A patent/NL7018258A/xx unknown

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