US3554754A - Light-sensitive reproduction material - Google Patents

Light-sensitive reproduction material Download PDF

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Publication number
US3554754A
US3554754A US692325A US3554754DA US3554754A US 3554754 A US3554754 A US 3554754A US 692325 A US692325 A US 692325A US 3554754D A US3554754D A US 3554754DA US 3554754 A US3554754 A US 3554754A
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US
United States
Prior art keywords
light
reproduction material
triphenylimidazole
sensitive
exposure
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US692325A
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English (en)
Inventor
Ernst-August Hackmann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kalle GmbH and Co KG
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Kalle GmbH and Co KG
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Filing date
Publication date
Application filed by Kalle GmbH and Co KG filed Critical Kalle GmbH and Co KG
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Publication of US3554754A publication Critical patent/US3554754A/en
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Expired - Lifetime legal-status Critical Current

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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
    • G03C1/675—Compositions containing polyhalogenated compounds as photosensitive substances

Definitions

  • the light-sensi tive material prepared in accordance therewith has the disadvantage that it is storable only to a limited extent since the leucotriphenylmethane dyes oxidize relatively rapidly even in the dark. As oxidizing agents there acts the oxygen of the air as well as the halogen compounds present in the light-sensitive layer or the decomposition products thereof.
  • the present invention provides a reproduction material with a light-sensitive layer which has a good storage life in the dark, can be fixed easily, and the activator of which is easily accessible.
  • the invention is based upon light-sensitive reproduction material which comprises a support and a light-sensitive layer thereon containing at least one compound oxidizable to give a dyestuif upon the action of light.
  • the reproduction material of the present invention is characterized in that the light-sensitive layer contains (1) At least one triphenylimidazole derivative of the general formula:
  • A, A, and A" may be equal or dilferent and may be OH or R R R and R may also be equal or different and may be H, alkyl, substituted alkyl, aryl, substituted aryl, halogen, nitro, amino, hydroxy, alkoxy or closed to form a mug,
  • At least one organic halogen compound splitting oif halogen upon exposure to light At least one organic halogen compound splitting oif halogen upon exposure to light.
  • triphenylimidazole derivatives The triphenylimidazole derivatives are prepared according to the general recipe by Davidson et al., J. Org. Chem, 2, 319 (1937) from the corresponding benzil, the corresponding aldehyde and ammonium acetate.
  • the organic halogen compounds used as activators are generally readily soluble in gasoline, ligroin or similar solvents which do not or only to a small extent attack the dyestuffs formed. By washing out with the indicated solvents, the reproduction materials can easily be fixed. Such activators may also be employed as they are volatile at slightly elevated temperatures and a material is then obtained which can be fixed by simply heating, i.e. in a dry manner.
  • tetrabromoand tetraiodopyrrole, tetraiodothiophene, and tetrabromothiophene, hexachloroethane, and tetraiodomethane are furthermore suitable. These compounds may be contained either alone or in admixture in the lightsensitive layer of the reproduction material of the present invention.
  • a solution containing one or more triphenylimidazole derivatives, one or more organic halogen compounds and, if desired, ferrocene as a sensitizer is applied to a support and the solvent is evaporated.
  • Suitable support materials are wood, glass, plastics film, metal foil, textiles, and particularly cellulose derivatives, such as cellulose triacetate and paper.
  • synthetic resins natural resins, waxes, e.g.
  • polystyrene, carboxymethyl cellulose, colophony, shellac, beeswax or carnauba wax may be added to the lightsensitive layers.
  • the quantitative proportion of the individual components of the layer may vary within wide limits. Preferred results are obtained when per 0.5 to 1.5 parts by weight of organic halogen compound 0.05 to 0.3 parts by weight of imidazole derivative is employed.
  • the ferrocene may be added in a quantity of 0.01 to 0.1 part by weight.
  • Coating may be performed in a usual manner by whirlcoating or spread-coating. Suitable spread-coating processes are the known immersion and roller application methods. The conditions under which the freshly spreadcoated or whirl-coated layers are liberated from the solvent depend on the evaporation properties of the solvent and of the halogen compounds. The drying temperature must be selected in a manner such that the solvent evaporates but not the halogen compound.
  • Processing of the reproduction material is performed in a usual manner. Exposure is carried out in contact or with lamps of strong intensity, also by projection. A visible image is obtained thereby. Preferably processed are negative originals since the reproduction material reverses the tone values and thus leads to positive copies. After exposure to light, fixation is necessary since the unexposed areas are still light-sensitive. Fixation is performed as already stated in the simplest way in that the exposed copy is washed out with a non-polar organic solvent, e.g. gasoline. After drying for a short time, the copy is ready for use. Production and use of the reproduction material of the present invention will be further illustrated by Way of the following examples.
  • Example 1 1 g. of pentabromoethane and 0.1 g. of triphenylimidazole derivative are dissolved in 10 ml. of acetone. A baryta paper is coated with this solution. After evaporation of the 'solvent exposure to light is carried out under an original in a photoprinting machine equipped with a high-pressure mercury light source. The reproduction material passes the light source at a speed of about 1 m./min. The following table shows the colour shade of the copy. Strong copies of the original are obtained. Fixation is carried out by washing out with gasoline.
  • Triphenylimidazole derivative of the copy Forrnula I Yellow II Red III Reddish brown IV Brown V Reddish brown VI Greyish blue VII Yellow Similar results are obtained with tetrabromomethane, iodoform, 3-nitro-tribromoacetophenone, 2,5-dimethyltribromoacetophenone, tribromomethylphenylsulphone.
  • Example 2 As described in Example 1, baryta paper is coated with solutions and, after evaporation of the solvent, wrapped in black film and stored at room temperature. A sample is taken therefrom every month and exposed to light and fixed as described in Example 1. Even after six months, the finished copies have no background and the lightsensitivity has also scarcely decreased.
  • Example 3 0.8 of 3-nitro-tribromoacetophenone, 0.1 g. of triphenylimidazole of Formula HI and 0.3 g. of a maleic acid anhydride/ styrene copolymer (Lytron 820 of Monsanto) are dissolved in ml. of acetone and a baryta paper is coated with the solution. After evaporation of the solvent, exposure to light is carried out under an original in a photoprinting machine equipped with a high-pressure mercury arc lamp. The reproduction material passes the light source at a speed of about 5 m./ min. A rusty brown image of the original is obtained in the exposed areas, which can be fixed by washing with gasoline.
  • a maleic acid anhydride/ styrene copolymer Lithacrylate
  • Example 4 l g. of tetrabromomethane, 0.2 g. of triphenylimidazole of Formula V, and 0.05 g. of ferrocene are dissolved in 10 ml. of acetone.
  • a *baryta paper is coated with the solution and, after evaporation of the solvent, exposed for 30 seconds under an original to a 200 watt incandescent lamp and then heated for about 2 minutes to 100 C. in the drying chamber.
  • the organic halogen compound as well as the ferrocene escape thereby so that the copy is fixed.
  • An intensive, rusty brown, negative image of the original is obtained.
  • Light-sensitive reproduction material which comprises a support and a light-sensitive layer thereon comprising:
  • R R R R and R may be the same or different and are H, alkyl, substituted alkyl, aryl, substituted aryl, halogen, nitro, amino, alkoxy, or any two of them closed to form a ring;
  • Light-sensitive reproduction material contains 0.05 to 0.3 part by weight of imidazole derivative and 0.01 to 0.1 part by weight of ferrocene per 0.5 to 1.5 parts by Weight of organic halogen compound.

Landscapes

  • 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)
US692325A 1966-12-24 1967-12-21 Light-sensitive reproduction material Expired - Lifetime US3554754A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEK61021A DE1289738B (de) 1966-12-24 1966-12-24 Lichtempfindliches Kopiermaterial

Publications (1)

Publication Number Publication Date
US3554754A true US3554754A (en) 1971-01-12

Family

ID=7229877

Family Applications (1)

Application Number Title Priority Date Filing Date
US692325A Expired - Lifetime US3554754A (en) 1966-12-24 1967-12-21 Light-sensitive reproduction material

Country Status (9)

Country Link
US (1) US3554754A (en, 2012)
AT (1) AT287487B (en, 2012)
BE (1) BE708391A (en, 2012)
DE (1) DE1289738B (en, 2012)
FR (1) FR1549807A (en, 2012)
GB (1) GB1198640A (en, 2012)
NL (1) NL6717028A (en, 2012)
SE (1) SE340749B (en, 2012)
ZA (1) ZA6707676B (en, 2012)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0691569A1 (en) 1994-07-04 1996-01-10 Kodak-Pathe Photographic emulsion with improved sensitivity

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL263755A (en, 2012) * 1959-01-16

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0691569A1 (en) 1994-07-04 1996-01-10 Kodak-Pathe Photographic emulsion with improved sensitivity

Also Published As

Publication number Publication date
NL6717028A (en, 2012) 1968-06-25
DE1289738B (de) 1969-02-20
BE708391A (en, 2012) 1968-06-21
FR1549807A (en, 2012) 1968-12-13
ZA6707676B (en, 2012)
GB1198640A (en) 1970-07-15
AT287487B (de) 1971-01-25
SE340749B (en, 2012) 1971-11-29

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