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

• Another requirement to be met by all diazotype materials is a light sensitivity as high as possible. It could be achieved to improve the coupling speed and lightsensitivity of diazonium compounds of the above type by certain combinations of substituents but the number of such compounds is still very small so that in the case of one-component material Where also the number of suitable coupling components is comparatively small only a limited number of azo dyes can be produced in the copy. Particularly such dyestuffs are desirable here as are suitable for the production of intermediate originals, i.e. dyestuffs absorbing in the same wave-length range as light-sensitive diazonium compounds.
• the present invention provides an improved diazonium compound useful in one-component diazotype materials comprising a support and a light-sensitive layer, charc CC acterized in that the light-sensitive diazonium compound has the general formula:
• R stands for a cycloalkyl or an aralkyl group with at most 10 carbon atoms
• R stands for an alkyl or a hydroxyalkyl group with l to 3 carbon atoms or
• R and R together with the nitrogen atom to which they are attached stand for a 6- or 7-membered heterocyclic radical
• R stands for the trifluoromethyl group
• X stands for the anion of the diazonium compound.
• the heterocyclic radicals may contain in known manner further substituents, e.g. alkyl groups.
• the anion of the diazonium compound may be derived from any acid suitable and usual for this purpose and, furthermore, the compound may be present in known manner as a double salt or as a complex salt, e.g. with ZnCl CdCl SnCl HBF or HPF
• the diazo compounds in accordance with the invention have a substantially higher light-sensitivity than the corresponding compounds non-substituted in the benzene ring and a considerably higher light-sensitivity than such diazo compounds as, instead of the CF group, carry other substituents, such as alkyl, halogen or alkoxy groups.
• the light-sensitivity is also considerably better compared with such compounds as contain a trifluoromethyl group in mposition to the diazo group.
• the coupling energy is markedly increased compared with such diazo compounds as carry no or another substituent in o-position to the diazo group.
• the new diazo compounds may be used for the semi-wet process whereas this is not the case with the corresponding compounds which are not substituted or substituted by other groups.
• the dyestuffs achieved by means of the claimed diazo compounds and suitable coupling components usually em ployed in the wet development are very fast to light and, owing to their light absorption in the ultraviolet range, suitable for the preparation of intermediate originals. Also the white in the background of the finished copies is markedly good.
• the diazo compound used can easily be obtained from the reaction product of piperidine with 3-chloro-6-nitrobenzotrifluoride (melting point 63 to 64 C.) by reduction (catalytically with Ni+-H and diazotization in the form of a perfectly crystalline tin chloride double salt.
• diazotype material is obtained which is markedly less lightsensitive, couples more slowly and, upon development, shows considerable bleeding of the dyestuffs.
• Diazotype material using the above diazo compound is additionally substantially more light sensitive than material using the corresponding S-trifiuoromethyl diazo compound.
• Example -2 White photoprinting base paper provided with a precoat of polyvinyl acetate and colloidal silica was coated with a solution of Gum arabic 0.3 Citric acid 0.5
• Example 3 Transparentized paper was coated with a solution of Citric acid 0.5 Sodium salt of naphthalene-1,3,6-trisulphonic acid 3.5
• the diazo compound from 2-trifluoromethyl-4-(N- methyl-N-benzyl) amino-aniline was prepared as follows:
• 5-chloro-2-nitro-trifluoromethyl-benzene was reacted with N-methyl-N-benzyl-amine in known manner to give 5-(N-methyl-N-benzyl)-amino 2 nitro-trifiuoromethylbenzene (melting point 69 to 70 C.), the nitro group was then catalytically reduced (Raney nickel and hydrogen) to give the amino group which was diazotized as usual in a hydrochloric acid medium. The diazo compound was separated with 40 percent fiuoboric acid in the form of tetrafluoborate. The analytically pure compound was obtained by recrystallization from methanol/ether (intensely yellow flakes).
• Example 4 Acetyl cellulose film with 2,5-acetyl groups per glucose unit, which has been superficially saponified to a depth of about 5p. was coated with a solution of Tartaric acid 0.5 Sodium salt of naphthalene-1,3,6-trisulphonic acid 3.5 Saponin 0.1 Diazo compound from 2 trifiuoromethyl 4 (N- methyl-N-cyclohexyl)amino-aniline (as zinc chloride double salt) 3.2
• the diazo compound used is prepared as follows:
• 5-chloro-2-nitro-trifluoromethyl-benzene was reacted in known manner with N-methyl-N-cyclohexylamine to give 5 (N-methyl-N-cyclohexyl)amino 2 nitro-trifluoromethyl-benzene (melting point 107 to 109 C.).
• the nitro compound thus obtained was catalytically reduced (Raney nickel and hydrogen) to give the corresponding amino compound which was diazotiazed in concentrated hydrochloride acid.
• the diazo compound was separated as tin chloride double salt, dried and digested several times with ether to obtain the yellow crystalline product.
• R stands for a cyclohexyl or benzyl group
• R stands for an alkyl or a hydroxyalkyl group with 1 to 3 carbon atoms or
• R and R together with the nitrogen atom to which they are attached stand for a saturated 6 membered heterocyclic radical
• R stands for the trifiuoromethyl group
• X stands for the anion of the diazonium compound.
• Diazotype material comprising a support and a coating thereon of a composition comprising a light-sensitive diazonium compound according to claim 1.
• diazonium compound is 1-diazo-2-trifluoromethyl-4 piperidinobenzene.
• diazonium compound is 1-diazo-2-trifluoromethyl-4- (4'-acetylpiperizino -benzene.
• diazonium compound is 1-diazo-2-trifiuoromethyl-4- morpholinobenzene.
• diazonium compound is 1-diazo-2-trifluoromethyl-4- (N-methyl-N-benzyl amino-benzene.
• diazonium compound is 1-diazo-2-trifluoromethyl-4- (N-me thyl-N-cy clohexyl) amino -benzene.

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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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Cited By (1)

• 1967
  • 1967-04-22 DE DE1572106A patent/DE1572106C3/de not_active Expired
• 1968
  • 1968-04-11 NL NL6805197A patent/NL6805197A/xx unknown
  • 1968-04-18 DK DK171468AA patent/DK119595B/da unknown
  • 1968-04-18 CH CH572468A patent/CH489824A/de not_active IP Right Cessation
  • 1968-04-18 US US722174A patent/US3563752A/en not_active Expired - Lifetime
  • 1968-04-19 SE SE5301/68A patent/SE342512B/xx unknown
  • 1968-04-19 GB GB18660/68A patent/GB1198767A/en not_active Expired
  • 1968-04-19 BE BE713948D patent/BE713948A/xx unknown
  • 1968-04-19 FR FR1577397D patent/FR1577397A/fr not_active Expired
  • 1968-04-19 AT AT385268A patent/AT277756B/de not_active IP Right Cessation
  • 1968-04-20 ES ES352983A patent/ES352983A1/es not_active Expired

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