Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
  • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
  • C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
  • C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
  • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
  • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
  • C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
• • 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

• R and R stand for alkyl, aralkyl or cycloalkyl, R for hydrogen or halogen atom, and X for an anion.
• diazo compounds when developed with one of the usual developers having pH values of 8 to 10 and containing phloroglucinol or resorcinol as coupling components, generally yield brown azo dyes when R; in Formula I is halogen, and black azo dyes when R is hydrogen and R is aralkyl.
• alkaline developers which contain polyvalent phenols as coupling components having the disadvantage that they do not keep for long because oxidation by the air sets in. For this reason, in recent times, developers are used having pH values below 8 which correspond to neutral or, preferably, acid reaction, and containing polyvalent phenols as coupling components.
• R stands for a phenylacetoamido, thiophenylacetoamido, benzoylacetoamido-arylmercapto, alkoxyphenyl or benzoylamino group
• R and R stand for alkyl, aralkyl or aryl.
• the coupling dyes which are achieved with acid developers in combination with the diazo compounds of formula II are in general of black colors and those achieved in combination with the rapid-coupling compounds of formula I are of violet hues.
• the commercially available diazo-type papers for acid development do only give copies with black or with violet lines.
• diazo compounds which, when developed with acid developers, yield colors other than those mentioned above, are of great interest for practical purposes. The reason for this is not only that the consumer is accustomed for example to brown lines from alkaline development, but also because brown dyes on transparent supports absorb ultraviolet light particularly well.
• diazotype material which contains, as light-sensitive substance in the reproduction coating, a diazo compound corresponding to the general formula [11 (III) wherein R and R stand for alkyl, aralkyl or cycloalkyl groups which may be substituted or not, or R, and R together with the nitrogen form a heterocyclic ring, and X is an anion, redbrown to brown-red, even brown-orange, coupling dyes of excellent covering power are obtained when acid developers are used.
• the diazo compounds according to formula III are distinguished by very great coupling activity, which is of advantage also when alkaline developers are used.
• their coupling activity and the covering power of the coupling dyes is lower than in the case of the corresponding compounds of formula III with a CF group in place ofR
• German Pat. No. 1,015,679 among other compounds, the chlorostannate of l-diazo-4-monocyclohexylamino-3- trifluoromethyl-benzene is mentioned.
• This compound as a secondary amino diazo compound, is not so light sensitive as the diazo compounds of formula III which bear a tertiary amino group in p-position to the diazo group. Moreover, when development is effected with acid developers, it gives violetblack hues which do not cover so well.
• the diazo compounds according to formula III may be prepared according to various methods. Their synthesis is particularly simple when a process is used which is another object of the present invention. In this process, 2-chloro-5-nitro-I- trifluoromethylbenzene is used as starting material and this is reacted with a secondary amine of the formula NHR R wherein R and R have the meaning given above, for example dimethylamine, diethylamine, diisopropylamine-di-n-butylamine, hydroxyethylpropylamine, methylbenzylamine, hydroxyethylbenzylamine, methylcyclohexylamine, pyrrolidine, morpholine, thiomorpholine, piperidine, N-alkylpiperazine, N-acylpiperazine.
• the alkyl, cycloalkyl and aralkyl groups or the heterocyclic ring may bear substituents which behave inert in the reaction.
• the nitro group of the resulting nitroaminotrifluoromethylbenzene with a tertiary amino group is then reduced to the amino group, the amino group is diazotized according to known methods, the anion X is added in the form of a soluble compound comprising the anion X, and in an amount sufficient to precipitate at least part of the formed diazonium compound as a salt of the above formula. Finally, the precipitated salt is separated from the remainder of the reaction mixture.
• the diazo compounds obtained after diazotation may be separated in the form of the chlorides as double salts with zinc chloride, cadmium chloride, stannic chloride, or as sulfates, borofluorides, hexafluorophosphates.
• the form in which the compound is present after separation has little influence on the property of the diazo compound.
• the diazo compounds according to formula III have good compatibility with the stabilizing agents usual in sensitizing solutions, such as 1,3,6-or 1,3,7-naphthalenetrisulfonic acid, boric acid, tartaric acid, citric acid, and others.
• photocopying base paper precoated photocopying base paper, transparent paper, transparentized paper, transparent paper provided with a coating of cellulose acetate which has been made hydrophilic, plastics films, e.g. polyester films or polycarbonate films, suitably pretreated for use as diazotype coating supports, can be used.
• Diazotype material which contains a diazo compound of formula Ill as light-sensitive substance in the reproduction coating, cannot only be used with acid developers but can also be developed in alkaline manner. The hues achieved are in general light brown to yellowish brown.
• Diazo compounds according to formula III whose coupling intensity is less great, can also be used for the preparation of so-called two-component diazotype material.
• the coupling component used together with EXAMPLE 1 As base paper suitable for the preparation of diazo-type material and which had previously been provided with a precoat of colloidal silicic acid and polyvinyl acetate was coated on the precoated side with a solution which contained in 1,000 parts by volume of water:
• citric acid 36.0 parts by weight of sodium naphthalene-l,3,6-trisulfonate
• the sensitized paper was imagewise exposed under a transparent original and developed with a solution which in 1,000 parts by volume of water contained:
• the pH value of the developer is 6. Brown images on a white background were obtained.
• EXAMPLE 2 Transparent paper which is coated on one side with a partially saponified cellulose acetate coating was coated on the precoated side with the sensitizing solution described in example 1, exposed under a line original after drying, and treated as in example 1. Brown-red lines with good covering power were obtained. In this case, too, the dye formed very rapidly directly after application of the developer.
• the sensitized base paper was image-wise exposed under a transparent line original and developed with a solution which, in 1,000 parts by volume of water, contained the following substances and had a pH value of6.3:
• borax 20.0 parts by weight of borax 20.0 parts by weight of trisodium phosphate 40.0 parts by weight of trisodium citrate 6.0 parts by weight of resorcinal 6.0 parts by weight of phloroglucinol 30.0 parts by weight of thiourea 2.0 parts by weight of the sodium salt of alkylnaphthalenesulfonic acid, e.g. the product marketed under the trademark Nekal A. Copies in neutral brown hues on a white background were obtained.
• EXAMPLE 4 An already precoated diazotype base paperof the type mentioned in example 1 was coated on the precoated side with a solution which contained in 1,000 parts by volume of water:
• the thus obtained sensitized paper was image-wise exposed under a transparent line original and developed with ammonia vapor. Copies with redbrown lines on a white background were obtained.
• diazo compound is 1-diazo-4-morpholino-3-trifluoromethylbenzyl diazonium borofluoride.
• diazotype material according to claim 1 wherein said diazo compound is l-diazo-4-pyrrolidino-3-trifluoromethylbenzyl diazonium zinc chloride.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (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)

Applications Claiming Priority (1)

Publications (1)

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Family Applications (1)

Country Status (10)

Cited By (2)

Families Citing this family (2)

• 1965
  • 1965-02-24 DE DE19651244575 patent/DE1244575C2/de not_active Expired
• 1966
  • 1966-02-11 ES ES0322947A patent/ES322947A1/es not_active Expired
  • 1966-02-14 NL NL6601840A patent/NL6601840A/xx unknown
  • 1966-02-21 BE BE676820D patent/BE676820A/xx unknown
  • 1966-02-21 CH CH248366A patent/CH466707A/de unknown
  • 1966-02-21 AT AT158966A patent/AT262763B/de active
  • 1966-02-22 FR FR50604A patent/FR1469814A/fr not_active Expired
  • 1966-02-23 SE SE02347/66A patent/SE326100B/xx unknown
  • 1966-02-23 GB GB7966/66A patent/GB1087024A/en not_active Expired
  • 1966-02-24 US US529650A patent/US3615570A/en not_active Expired - Lifetime

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