US2336309A - Diazotype photographic material - Google Patents

Diazotype photographic material Download PDF

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Publication number
US2336309A
US2336309A US395822A US39582241A US2336309A US 2336309 A US2336309 A US 2336309A US 395822 A US395822 A US 395822A US 39582241 A US39582241 A US 39582241A US 2336309 A US2336309 A US 2336309A
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Prior art keywords
naphthol
group
acid
ethyl
diazotype
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Expired - Lifetime
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US395822A
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English (en)
Inventor
John M Snell
Weissberger Arnold
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Eastman Kodak Co
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Eastman Kodak Co
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Publication date
Priority to FR956666D priority Critical patent/FR956666A/fr
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Priority to US395822A priority patent/US2336309A/en
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Publication of US2336309A publication Critical patent/US2336309A/en
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Expired - Lifetime legal-status Critical Current

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    • 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

  • This invention relates to diazotype photographic materials. More particularly, it relates to diazotype copying materials wherein thellght sensitive compound is a diazo derivative of an arylamine having the general formula:
  • X B l group More specifically, X can be hydrogen,
  • R. can be methyl, ethyl, propyl, butyl, fl-methoxyethyl, hydroxyethyl, p -dihydrompropyl.
  • R1 can be carbamyl, methoxy, ethoxy, acetyl, carboxylic acid methyl ester, carboxylic acid ethyl ester, carborwlic acid propyl ester, methanesulfonamido, ethanesulfonamido, furyl, tetrahydrofuryl, and similar kind of groups.
  • diazo derivatives of the above described substituted phenylene diamines are stable compounds under ordinary conditions, but decompose more or less completely on exposure to light. Since they are also capable of condensing with certain aromatic coupling compounds, as well as with their own partial decomposition products, in the presence of alkaline substances to form fast azo dyes, we have found further that our diam derivatives are valuable as light sensitive components in diazotype photographic copying materials.
  • the alkaline processing consists ordinarily of subjecting the exposed diazotype sheet to an atmosphere of ammonia, but it is also possible to develop the image by means of a dilute aqueous solution of an alkylolamine such as triethanolamine or by means of steam in which case the sensitized coating must contain a suitable alkali incorporated therein.
  • the base or support carrying or containing the light sensitive compounds can be paper, cloth or a film such as prepared rrom cellulose nitrate, cellulose acetate, cellulose acetatepropionate, regenerated cellulose, and the like, a glass plate or sheet metal, the sensitizing substance being applied by coating, dipping, brushing, spraying, dusting or by any other means known to one skilled in the art.
  • sensitizing compounds can be applied from a solution containing one or more of our diazo compounds together with one or more selected coupling components and may also have present one or more stabilizing compounds selected from the group including hydrochloric acid, boric acid, tartaric acid, thiourea, and the like. Ordinarily, however, the light sensitive compounds and the coupling compounds are dissolved in separate solutions and applied to the sheet material to be sensitized in sequence. The stabilizers are usually incorporated in the chemo salt solution.
  • each .apphcatromtne sheet may be dried, if desired.
  • Another modification is to add a thickening or emulsifying agent to the solution 'or solutions such as gelatin, polyvinyl alcohol, polyvinyl phthalate, cellulose acetate-phtnalate, gum tragacantn, a higher fatty acid glyceryl sulfate and similar kind of substances.
  • the solution concentrations of the sensitizing compounds can be varied within fairly wide limits, the preferred range being up to about 2% by weight of the diazo compound, and about the same concentration, of the coupling compound. Good results have also been obtained with concentrations as high as 4% by weight of the respective components.
  • the stabilizers can also :18 varied within fairly wide limits of concentra- It is an object of our invention, therefore, to provide diazotype photographic copying materials which combine the advantages of good stability, high degree of sensitivity to light, and produce prints which are characterized by excellent keeping qualities, good sharpness and contrast.
  • the substituted phenylene diamines of our invention can;be prepared by a number of methods.
  • Onemethod is the react an ortho or para nitrochlorobenzene with the desired secondary aliphatic-amine, and then reduce with ammonium sulfide or with a nickel catalyst.
  • N-ethyl-N-(4-amino-3- methylphenyl) glycineamide can be prepared by starting with N-ethyl-N-(3-methylphenyl) -glycineamide,,converting to the p-nitro derivative by nitration in the presence of sulphuric acid, isolating the product by crystallization, dissolving the crystals in ethanol and hydrogenating over nickel at temperatures of 50-150 0.
  • Another method of preparing our substituted phenylene diamines is to startwith an N-alkyl-m-toluidine and condense it with an aliphatic halide of the type desired tobe introduced, treat the product with sodium nitrite and hydrochloric acid to convert to the nitroso derivative, and then reduce to the substituted phenylene diamine with zinc and hydrochloric acid-
  • furylamine intermediates employed in the above reactions they can be prepared as described in McNally and Dickey, U. 8. Patent 2,191,030, issued Feb. 20, 1940, and Cliiford, U. s.
  • N-hydroxyalkylphenylene diamines can be prepared by reacting phenylene diamine with analkyleneoxide as described in Wendt, U. S. Patent 2,108,243, issued Feb. 15,
  • Example 2 A solution containing the diazonium compound of approximately 2 grams of N-ethyl-N-(4- amino-a-methylphenyl)-glycineamide, 4 grams of concentrated hydrochloric acid, 4 grams of boric acid, 8 grams of tartaric acid, 0.4 gram of thiourea and c. c. of water was applied to a piece of white paper. The excess liquid was removed and the paper then dipped in a 1% solution of p-naphthol in ethyl alcohol. After drying, the sensitized paper was exposed and developed as in Example 1. The print had a dark purple coloured image on a white field. The unused. sensitized paper showed good keeping qualities when treated at 48 C. for 5 days.
  • N-ethyl-N-(4-amino-3-methylphe'nyD-glycineamide there was substituted an equavilent amount of N-(p-methoxyethyl)-N-(4-amino- 3 -methylphenyl) glycineamide which produced a purple image on a white field, and N-methyl-N-paminophenyl-glycineamide which produced a red-brown image on a white field.
  • the unused, sensitized papers in each case showed good keeping test results.
  • Example 3 A solution made up similar to that of Example 2, but employing as the light sensitive material the diazonium compound of N-ethyl-N-(4- amino-3-methylphenyl) -glycine ethyl ester sulfate z The image of-theprint obtained was purple in color on a very pale tan field. The keeping test was satisfactory.
  • Example 5 A piece of white paper was sensitized, exposed and developed as described in Example 2, except the diazonium compound was a. derivative of 2- amino-5 (ethyl-p-methoxyethylamino)-toluene CHrO 021(4 $11 The image of the print obtained was dark purple in color on a white field. The keeping test was satisfactory.
  • Example 6 A piece of white paper was sensitized, exposed and developed as described in Example 2, except the diazonium compound was a derivative of 2- amino (p-hydroxyethyl tetrahydroiuriurylamino) -toluene 110- can N-QNH, t Jan-o4 Hi B c-CH;
  • Example 7 A piece of white paper was sensitized, exposed and developed as described in Example 2, except the light sensitive compound was a diazo derivative of 2-amino-5-acetonyl ethylamino-toluene sulfate CSHJ CHaC OCH;
  • amylbenzene-sulfon)amido-l-naphthol S-(N-benzyl-N- n valeryl) amido -1- naphthol, 2-bromoacetyl-1- naphthol, Z-cinnamoyl-l-naphthol, 2,4-dichloro- 5 [p (p-benzamido) -benzamidol-1 naphthol, 2,4 dichloro 5 palmitylamino i-naphthol, 5-
  • a diazotype photographic material comprising a light sensitive diazo derivative of a compound having the general formula:
  • n represents a whole number not greater than 3
  • X represents a member selected from the group consisting of hydrogen, a halogen, an alkyl group, an alkoxy group, an acylamino group, and a sulphonic acid group
  • R represents a member selected from the group consisting of an alkyl group, a hydroxyalkyl group, and an alkoxyallwl group
  • R1 represents a member selected from the group consisting of an alkoxy group, a fatty acid acyl group, a carboxylic acid alkyl ester group, an alkylsulionamido group, a furyl group, a carbamyl group, and a tetrahydrofuryl group.
  • a diazotype photographic material comprising a light sensitive diazo derivative 01' a compound having the general formula:
  • n represents a whole number not greater than 3
  • X represents a member selected from the group consisting of hydrogen, a halogen, an alkyl group, an alkoxy group, an acylamino group, and a sulphonic acid group
  • R represents a member selected from the group consisting of an alkyl group, a hydroxyalkyl group, and an alkoxyalkyl group.
  • a diazotype photographic material comprising a light sensitive diazo derivative of a compound having the general formula:
  • a diazotype photographic material comprising a light sensitive diazo derivative of a compound having the general formula:
  • n represents a whole number not greater than 3
  • x represents a member selected from the group consisting of hydrogen, a halogen, an alkyl group, an alkoxy group, an acylamino group. and a sulphonic acid group
  • R represents a member selected from the group consisting of an alkyl group, a hydroxyalkyl group, and an alkoxyalkyl group.
  • a diazotype photographic material comprising a light sensitive diazo derivative of a norm pound having the general formula:

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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)
US395822A 1941-05-29 1941-05-29 Diazotype photographic material Expired - Lifetime US2336309A (en)

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FR956666D FR956666A (OSRAM) 1941-05-29
US395822A US2336309A (en) 1941-05-29 1941-05-29 Diazotype photographic material

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2528460A (en) * 1946-10-12 1950-10-31 Gen Aniline & Film Corp Diazotype compositions containing ethylene oxide derivatives of amino diazos
US2529464A (en) * 1946-09-23 1950-11-07 Gen Aniline & Film Corp Diazotype composition containing n-hydroxyethyl-m-toluidine-p-diazos
US2616803A (en) * 1948-03-11 1952-11-04 Leonard E Ravich Diazotype dyeing and printing of web or sheet material
US2655448A (en) * 1949-03-08 1953-10-13 Gen Aniline & Film Corp Diazotype photoprinting process
US2733144A (en) * 1951-03-28 1956-01-31 Method of producing photographic
US2741558A (en) * 1952-03-11 1956-04-10 Grinten Chem L V D Process for the manufacture of diazotype copies
US2773768A (en) * 1951-03-20 1956-12-11 Grinten Chem L V D Light-sensitive diazotype material
US3300471A (en) * 1964-01-02 1967-01-24 Universal Oil Prod Co p-(nu-cyanoalkyl-nu-hydrocarbylamino)-benzenediazonium chlorides
US3719491A (en) * 1968-06-18 1973-03-06 Gaf Corp Diazo-type reproduction process
US4149888A (en) * 1972-06-26 1979-04-17 Gaf Corporation Transparent photographic masks
US4618561A (en) * 1983-12-06 1986-10-21 Canon Kabushiki Kaisha Monomolecular record memory medium with photosensitive diazonium salt
US4762767A (en) * 1983-07-09 1988-08-09 Merck Patent Gesellschaft Mit Beschrankter Haftung Negatively operating photoresist composition, with radiation-absorbing additives
US4849323A (en) * 1986-08-12 1989-07-18 Matsushita Electric Industrial Co., Ltd. Pattern forming method using contrast enhanced material

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2529464A (en) * 1946-09-23 1950-11-07 Gen Aniline & Film Corp Diazotype composition containing n-hydroxyethyl-m-toluidine-p-diazos
US2528460A (en) * 1946-10-12 1950-10-31 Gen Aniline & Film Corp Diazotype compositions containing ethylene oxide derivatives of amino diazos
US2616803A (en) * 1948-03-11 1952-11-04 Leonard E Ravich Diazotype dyeing and printing of web or sheet material
US2655448A (en) * 1949-03-08 1953-10-13 Gen Aniline & Film Corp Diazotype photoprinting process
US2773768A (en) * 1951-03-20 1956-12-11 Grinten Chem L V D Light-sensitive diazotype material
US2733144A (en) * 1951-03-28 1956-01-31 Method of producing photographic
US2741558A (en) * 1952-03-11 1956-04-10 Grinten Chem L V D Process for the manufacture of diazotype copies
US3300471A (en) * 1964-01-02 1967-01-24 Universal Oil Prod Co p-(nu-cyanoalkyl-nu-hydrocarbylamino)-benzenediazonium chlorides
US3719491A (en) * 1968-06-18 1973-03-06 Gaf Corp Diazo-type reproduction process
US4149888A (en) * 1972-06-26 1979-04-17 Gaf Corporation Transparent photographic masks
US4762767A (en) * 1983-07-09 1988-08-09 Merck Patent Gesellschaft Mit Beschrankter Haftung Negatively operating photoresist composition, with radiation-absorbing additives
US4618561A (en) * 1983-12-06 1986-10-21 Canon Kabushiki Kaisha Monomolecular record memory medium with photosensitive diazonium salt
US4849323A (en) * 1986-08-12 1989-07-18 Matsushita Electric Industrial Co., Ltd. Pattern forming method using contrast enhanced material

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Publication number Publication date
FR956666A (OSRAM) 1950-02-02

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