US3489568A - Light-sensitive imaging materials containing azole/aldehyde condensates and halogenated hydrocarbons - Google Patents

Light-sensitive imaging materials containing azole/aldehyde condensates and halogenated hydrocarbons Download PDF

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Publication number
US3489568A
US3489568A US481117A US3489568DA US3489568A US 3489568 A US3489568 A US 3489568A US 481117 A US481117 A US 481117A US 3489568D A US3489568D A US 3489568DA US 3489568 A US3489568 A US 3489568A
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light
ferrocene
aldehyde
condensation product
benzaldehyde
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US481117A
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English (en)
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Ernst August Hackmann
Johannes Munder
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Kalle GmbH and Co KG
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Kalle GmbH and Co KG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/333—Radicals substituted by oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/12—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered 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
    • G03C1/675—Compositions containing polyhalogenated compounds as photosensitive substances

Definitions

  • Light-sensitive, negative-working reproduction materials suitable for use in image copying with ultraviolet light source are prepared by coating a support with a light-sensitive imaging composition comprising a halogenated hydrocarbon, and a condensation product of (a) an aldehyde and (b) androgen-containing, S-membered heterocyclic ring compound.
  • the improved imaging material may be sensitized to incandescent light sources by the addition of a ferrocene.
  • the present invention relates to light-sensitive layers and refers more particularly to reproduction materials utilizing such novel, highly light-sensitive negative-working layers.
  • methyl indoles and phenyl indoles such as 2,3-dimethyl indole and l-methyl- 2-phenyl-indole, form dyestuffs with halogenated hydrocarbons, such as bromoform, iodoform and the like, when they are exposed to ultraviolet radiation.
  • halogenated hydrocarbons such as bromoform, iodoform and the like
  • one object of the present invention is to pro- United States Patent vide light-sensitive materials which overcome the disad- I tion materials having superior light sensitivity to the ma- I terials previously known.
  • condensation products of nitrogen-containing heterocyclic compounds having a quasiaromatic 5-membered ring with aldehydes form dyestuffs when exposed to ultraviolet light. This efiect is considerably increased by the presence of halogenated hydrocarbons.
  • the light-sensitivity of the condensation products of' nitrogen-containing, heterocyclic quasi-aromatic compounds having a S-membered ring and the aldehydes is capable of a particularly significant increase, when not only halogenated hydrocarbons are added, but-also ferrocene or substituted ferrocene.
  • a sensitivity to light in the visible region of the spectrum is thus obtained, which is satisfactory for practical purposes.
  • aromatic aldehydes such as benzaldehyde, 3,4-methylene-dihydroxy-benzaldehyde, or dimethylaminobenzaldehyde may be added for improving the light sensitivity.
  • the light-sensitive material of the present invention comprises a support such as paper, metal or plastic film such as polyester film, cellulose ester film or saponified cellulose, and a light-sensitive layer including at least one condensation product of one or more nitrogen-containing, heterocyclic, quasi-aromatic compounds having a 5-membered ring with one or more aldehydes.
  • the compound may be substituted.
  • the layer may also contain at least one condensation product of one or more nitrogencontaining, heterocyclic, quasi-aromatic compounds having a 5-membered ring with one or more aldehydes and at least one amine.
  • the layer includes at least one halogenated hydrocarbon.
  • Condensation products of nitrogen-containing, heterocyclic compounds having a quasi-aromatic 5-membered ring with aldehydes according to the present invention are those compounds obtained from two moles of indole or a mixture of different indoles, which may be substituted at the indole nucleus as well as at the aromatic nucleus, and one mole of aldehyde according to the following equation:
  • reaction is performed in a known manner in an alcoholic solution, in the presence of acid catalysts such as mineral acids or zinc chloride (see E. Fischer Liebigs Ann. Chem, 242, page 372, 1887). It is possible to start with one substituted indole or with a mixture of substituted indoles to form asymmetrical condensation products as well as symmetrical products.
  • acid catalysts such as mineral acids or zinc chloride
  • R may be hydrogen, alkyl, aryl, substituted aryl, alkenyl, aralkyl, or a heterocyclic radical.
  • examples of such compounds are: benzaldehyde; 4-dimethylaminobenzaldehyde, 3,4-dichloro-benzaldehyde; 4-chloro-benzaldehyde; 3-nitrobenzaldehyde; 3,4-methylene-dihydroxybenzaldehyde; 4-hydroxy-benzaldehyde; cinnamic aldehyde; 4-amino-cinnamic aldehyde; indole-3-aldehyde;
  • phenyl-pro ionaldehyde phenyl-pro ionaldehyde; formaldehyde, acetaldehyd e and X which may be identical or dilferent and may be hydroxyl, alkoxy, halogen, carboxyl, hydrogen or carboxyalkyl.
  • condensation products of indoles and aldehydes instead of the condensation products of indoles and aldehydes, analogous products of pyrroles, pyrazoles, imidazoles, 1,2-substituted pyrazolones, triazoles, and tetrazoles with the aldehydes may be usedfor the prepara-: tion of the present light-sensitive layers. Mixtures of these compounds may be used forthe preparation of the condensation products.
  • Pyrroles used according to the present invention in.- clude pyrrole itself and derivatives having up to four substituents with one alpha-position with respect to the 3 nitrogen being left unsubstituted.
  • the pyrroles have the following general formula:
  • R R and R may be identical or different and have the meaning given above for R R R and R in connection with the indoles.
  • the condensation products were prepared in accordance with the method described by L. Knorr in Liebigs Annalen der Chemie, 238, page 214 (1887).
  • condensation products of triazole or substituted triazoles used according to the present invention are derived from the following general formula:
  • R and R may be identical or different and have the meaning stated above in connection with R R R and R for indole.
  • the condensation products are prepared analogously to the condensation products of the indoles.
  • condensation products of tetrazole are derived from tetrazoles of the following general formula:
  • R has the meaning stated above for R R R and R for the indoles.
  • the tetrazoles may be reacted with aldehydes in the same manner as the indoles.
  • a further group of condensation products of the above named compounds with a nitrogen containing quasi-aro matic -membered ring is obtained by reacting them with an aldehyde and an amine, preferably a secondary amine, in a kind of Kunststoff-reaction.
  • an aldehyde and an amine preferably a secondary amine, in a kind of Kunststoff-reaction.
  • the compounds used are indole, salicylic aldehyde, and piperidine;
  • Secondary amines are preferred as the amine component in the reaction stated above.
  • Examples are dialkylamines, alkyl aryl amines, and heterocyclic amines, such as dimethyl amine, methyl aniline, piperidine, pyrrolidine, and morpholine.
  • X stands for chlorine, bromine or iodine
  • R R and R may be identical or different and may stand for chlorine, bromine, iodine, hydrogen, alkyl (which may be substituted by chlorine, bromine or iodine), aryl, aralkyl, alkenyl or a heterocyclic group.
  • carboxylic acid chlorides and their derivatives, and halogenated synthetic substances such as chlorinated rubber may be used.
  • the light-sensitivity of layers consisting of condensation products of nitrogen-containing heterocyclic quasi-aromatic 5-membered ring compounds with aldehydes and halogenated hydrocarbons may be considerably increased, particularly in the visible range of the spectrum, by adding ferrocene or a substitution product of ferrocene.
  • Suitable substituted ferrocenes are: diacetyl ferrocene, dipropionyl ferrocene, dibenzoyl ferrocene, bis-(3-nitrobenzoyl)-ferrocene, bis-(4-dimethyl-amino-benzoyl) ferrocene, and ferrocene dicarboxylic acid.
  • aromatic aldehydes such as benzaldehyde, 3,4-methylene-dihydroxy-benzaldehyde, dimethylamino-benzaldehyde, and indole-3-aldehyde may be added.
  • the reproduction materials prepared in accordance with the invention are highly light-sensitive and practically odorless.
  • the condensation products possess relatively high melting points so that they do not escape from the layer when the material is stored.
  • a solution containing one or more of the condensation products and one or more halogenated hydrocarbons is applied to a support and the solvent is evaporated. Ferrocene and/or aldehyde may be added to the solution.
  • Suitable supporting materials are wood, glass, plastic films, metal foils, fabrics, and cellulose derivatives, such as cellulose triacetate and paper.
  • natural or synthetic resins or waxes may be added to the light-senstitive substances.
  • an essential component of the light-sensitive layer for example, the halogenated hydrocarbon
  • Suitable light sources for the present process are commercial mixed light and ultraviolet radiators. When ferrocene is added, customary incandescent bulbs are sufficient.
  • fixation of the exposed materitls is effected by a brief heattreatment at C. to 120 C., (for example, in a drying cupboard, by means of heated plates, or an infrared source, or by passing the materials over a heated roller).
  • Halogenated hydrocarbons which are not volatile under these conditions may be removed by washing with organic solvents, such as ligroin, petrol ether, and the like.
  • the material of the present invention may be used for the preparation of contact copies as well as reflex copies. It is particularly suitable for the production of reenlargements from microfilms.
  • EXAMPLE 1 An absorbent base paper customarily used for reproduction purposes was soaked with a solution of 0.2 g. of a condensation product of 2-methyl-indole and 4-dimethylamino-benzaldehyde in 10 m1. of acetone. After evaporation of the solvent, the coated paper was exposed for two minutes to a carbon arc lamp under a master. A negative red copy of the master was produced.
  • the condensation product was prepared by dissolving two moles of Z-methyl-indole and 1 mole of 4-dimethy1- amino-benzaldehyde in ethanol and adding a small quantity of hydrochloric acid. When the reaction mixture was heated on a water bath, the condensation product precipitated in crystalline form.
  • EXAMPLE 2 An absorbent base paper customarily used for reproduction purposes was soaked with a solution of 0.2 g. of the condensation product of Z-methyl-indole and 4-dimethylamino-benzaldehyde and 1.0 g. of tetrabromomethane in 10 ml. of acetone. After evaporation of the solvent, the material was exposed for five seconds to a carbon arc lamp under a master. The exposed paper was fixed by heating for two minutes at C. in a drying cupboard. A negative red copy of the master was obtained.
  • EXAMPLE 3 An absorbent base paper customarily used in the reproduction field was soaked in a solution of 0.2 g. of the condensation product of Z-methyl-indole and 4-dimethyl amino-benzaldehyde, 1.0 g. of tetrabromomethane, and 0.3 g. of ferrocene in 10 ml. of acetone. After evapo ation of the solvent, the material was exposed for ten seconds to a ZOO-watt incandescent bulb under a master. The exposed paper was then fixed by heating it for two minutes to 100 C. in a drying cupboard. A negative red copy of the master was obtained.
  • EXAMPLE 4 An absorbent base paper customarily used in the reproduction field was soaked in a solution of 0.2 g. of the condensation product of Z-methyl-indole and cinnamic aldehyde, 1.0 g. of tetrabromomethane, and 0.3 g. of ferrocene in 10 ml. of acetone. After evaporation of the solvent, the material was exposed for ten seconds to a ZOO-watt incandescent bulb under a master. The exposed paper was heated for two minutes to 100 C. in a drying cupboard as in Example 3. A negative green copy of the master was obtained. The condensation product was prepared as described in Example 1.
  • EXAMPLE 5 An acetate film was coated with a solution of 0.1 g. of the condensation product of 2-methyl-indole, benzaldehyde piperidine, 1 g. of tetrabromomethane, 0.3 g. of ferrocene, and 0.5 g. of polystyrene in 10 ml. of a solvent mixture consisting of equal parts of acetone and trichloroethylene by volume. After evaporation of the solvent, the material was exposed for one second to a carbon arc lamp under a master. The exposed film was fixed by passing it under an infrared radiator. A red copy of the master was obtained which could be used for making futher reproductions on photoprinting paper.
  • the condensation product was prepared by dissolving one mole of 2-methyl-indole, 0.96 mole of benzaldehyde and 0.59 mole of piperidine in three times their own quantity of ethanol, allowing the mixture to stand overnight, and then adding water until it became turbid, whereupon the condensation product precipitated in crystalline form.
  • EXAMPLE 6 An absorbent base paper as customarily used in the reproduction field was soaked with a solution of 0.2 g. of the condensation product .of 1-phenyl-2,3-dimethylpyrazolone-(S) and benzaldehyde, 0.3 g. of ferrocerie, and 1.0 g. of tetrabromomethane in ml. of a solvent mixture consisting of equal parts by volume of acetone and trichloroethylene.
  • a 500-watt projector lamp an 8 enlargement was produced on this paper from a silver halide negative film. The exposure time was 45 seconds. After fixation in a drying cupboard, a distinct yellow-brown image was obtained on a colorless background.
  • the condensation product was prepared by dissolving 1-phenyl-2,3-dimethyl-pyrazolone in benzaldehyde and adding a small quantity of concentrated hydrochloric acid.
  • the condensation product precipitated in the form of the hydrochloride, from which it was recovered by means of sodium hydroxide solution.
  • EXAMPLE 7 An absorbent base paper was soaked in a solution of 0.2 g. of the condensation product of 2-methyl-4-phenyl- 3-acetyl-pyrrole and benzaldehyde, 0.3 g. of ferrocene, and 1.0 g. of tetrabromomethane in 10 ml. of a mixture consisting of equal parts by volume of acetone and trichloroethylene, and the solvent was evaporated. In the manner described in Example 6, a re-enlargement was produced from a silver halide negative film. A rust-brown copy was obtained on a colorless background. The condensation product was prepared as described in Example 1.
  • EXAMPLE 8 A baryta paper was coated with a solution of 0.1 g. of the condensation product of l-methyl-Z-phenyl-indole and cinnamic aldehyde, 0.2 g. of 3,4-methylene-dihydroxybenzaldehyde, 0.3 g. of ferrocene, and 1.5 g. of tetrabromomethane in 10 ml. of acetone and then dried. On the reproduction material prepared in this manner, an enlargement at a scale of 1:10 was produced from a silver halide negative film by means of a 500-watt projector lamp. The exposure time was ten seconds. After exposure, the material was fixed in a drying cupboard at a temperature of 100: C. A green, easily legible image was obtained on a colorless background.
  • the condensation product was prepared as described in Example 1.
  • EXAMPLE 9 EXAMPLE 1() A baryta paper was coated with a solution of 0.1 gram of the condensation product of 1-phenyl-2,3-dimethylpyrazolone-(5) and benzaldehyde, 0.2 gram of 3,4- methylene-dihydroxy-benzaldehyde, 0.3 gram of ferrocene, and 1.5 gram of tetrabromomethane in 10 ml. of
  • a light-sensitive reproduction material comprising ,(a) a support; and v (b) a light-sensitive layer coated on said support, said layer comprising i (1) a halogenated hydrocarbon, and
  • condensation product includes a secondary amine
  • R and R are each independently selected from the group consisting of hydrogen, alkyl, alkenyl, aralkyl, and aryl;
  • X is selected from the group consisting of hydrogen, hydroxy, alkoxy, halogen, carboxyl and carboxyalkyl; and
  • n is from one to four; and said aldehyde has the general formula:
  • R is selected from the group consisting of hydrogen, alkyl, aryl, substituted aryl alkenyl, aralkyl and heterocyclic ring.
  • R R R and R are each members independently selected from the group consisting of hydrogen, alkyl, alkenyl, acyl, aralkyl, alkaryl and aryl.
  • R R and R are each members independently selected from the group consistingofhydrogen, alkyl, alkenyl, aralkyl, alkaryl, and aryl.
  • R and R are each members independently selected from the group consisting of hydrogen, alkyl, alkenyl, aralkyl, alkaryl and aryl.
  • R is a member selected from the group consisting of hydrogen, alkyl, alkenyl, aralkyl, alkaryl and aryl. 13.
  • X is a member selected from the group consisting of chlorine, bromine, and iodine
  • R R and R are each independently selected members from the group consisting of chlorine, bromine, iodine, hydrogen, halogen-substituted alkyl, aryl, aralkyl, alkyl, alkenyl and heterocyclic ring.
  • halogenated hydrocarbon is selected from the group consisting of: tetrabromomethane, 4-bromo-omega, omega, omega-tribromo)-acetophenone; 2,4-dimethyl-(omega, omega, omega-tribromo)-acetophenone; and 3-nitro- (omega, omega, omega-tribromo)-acetophenone.

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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)
  • Pyrrole Compounds (AREA)
  • Indole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
US481117A 1964-08-22 1965-08-19 Light-sensitive imaging materials containing azole/aldehyde condensates and halogenated hydrocarbons Expired - Lifetime US3489568A (en)

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DEK53818A DE1258734B (de) 1964-08-22 1964-08-22 Lichtempfindliche Schicht

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AT (1) AT264289B (de)
BE (1) BE668530A (de)
CH (1) CH453889A (de)
DE (1) DE1258734B (de)
GB (1) GB1074913A (de)
NL (1) NL6510549A (de)
SE (1) SE322687B (de)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3847607A (en) * 1970-02-04 1974-11-12 Canon Kk Organic photoconductors sensitized by free radical liberators and organometallic compounds
US3957288A (en) * 1972-12-28 1976-05-18 Agfa-Gevaert N.V. Thermographic recording material
US3958815A (en) * 1972-12-28 1976-05-25 Agfa-Gevaert N.V. Pressure-sensitive recording materials
FR2358433A1 (fr) * 1976-07-16 1978-02-10 Ciba Geigy Ag Bis-tetrazoles utilisables comme agents d'expansion de matieres thermoplastiques

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4332795A1 (de) * 1993-09-27 1995-03-30 Bayer Ag Aufzeichnungsmaterial für Bilder oder Daten

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3056673A (en) * 1959-01-16 1962-10-02 Horizons Inc Print-out and developable-out photographic processes
US3164467A (en) * 1963-03-14 1965-01-05 Horizons Inc Ultraviolet sensitive print-out compositions and process for image-wise exposure and fixing of same
US3335008A (en) * 1964-04-02 1967-08-08 Eastman Kodak Co Photographic elements containing ferrocene derivative and method of processing

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3056673A (en) * 1959-01-16 1962-10-02 Horizons Inc Print-out and developable-out photographic processes
US3164467A (en) * 1963-03-14 1965-01-05 Horizons Inc Ultraviolet sensitive print-out compositions and process for image-wise exposure and fixing of same
US3335008A (en) * 1964-04-02 1967-08-08 Eastman Kodak Co Photographic elements containing ferrocene derivative and method of processing

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3847607A (en) * 1970-02-04 1974-11-12 Canon Kk Organic photoconductors sensitized by free radical liberators and organometallic compounds
US3957288A (en) * 1972-12-28 1976-05-18 Agfa-Gevaert N.V. Thermographic recording material
US3958815A (en) * 1972-12-28 1976-05-25 Agfa-Gevaert N.V. Pressure-sensitive recording materials
FR2358433A1 (fr) * 1976-07-16 1978-02-10 Ciba Geigy Ag Bis-tetrazoles utilisables comme agents d'expansion de matieres thermoplastiques

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GB1074913A (en) 1967-07-05
SE322687B (de) 1970-04-13
CH453889A (de) 1968-03-31
BE668530A (de) 1966-02-21
DE1258734B (de) 1968-01-11
NL6510549A (de) 1966-02-23
AT264289B (de) 1968-08-26

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