US3326686A - Light-sensitive two-component diazotype materials adapted for heat development - Google Patents

Light-sensitive two-component diazotype materials adapted for heat development Download PDF

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Publication number
US3326686A
US3326686A US284364A US28436463A US3326686A US 3326686 A US3326686 A US 3326686A US 284364 A US284364 A US 284364A US 28436463 A US28436463 A US 28436463A US 3326686 A US3326686 A US 3326686A
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United States
Prior art keywords
light
acid
sensitive
salt
sensitizing
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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
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US284364A
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English (en)
Inventor
David I Randall
Harlan B Freyermuth
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GAF Chemicals Corp
R Q O HOLDING CO Inc
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General Aniline and Film Corp
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Filing date
Publication date
Application filed by General Aniline and Film Corp filed Critical General Aniline and Film Corp
Priority to US284364A priority Critical patent/US3326686A/en
Priority to US292097A priority patent/US3301679A/en
Priority to US292114A priority patent/US3166422A/en
Priority to US292066A priority patent/US3294534A/en
Priority to US292115A priority patent/US3255011A/en
Priority to US292098A priority patent/US3298834A/en
Priority to GB21014/64A priority patent/GB1063132A/en
Priority to NL6406013A priority patent/NL6406013A/xx
Priority to BE648593D priority patent/BE648593A/xx
Priority to FR976481A priority patent/FR1405427A/fr
Application granted granted Critical
Publication of US3326686A publication Critical patent/US3326686A/en
Assigned to R Q O HOLDING COMPANY INC reassignment R Q O HOLDING COMPANY INC ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: GAF CORPORATION
Anticipated expiration legal-status Critical
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
    • G03C1/52—Compositions containing diazo compounds as photosensitive substances
    • G03C1/61—Compositions containing diazo compounds as photosensitive substances with non-macromolecular additives

Definitions

  • Light-sensitive diazotype materials susceptible to heat development as disclosed in the Greig Patent are subject to the disadvantage that the relatively high acidity of the sensitizing composition causes deterioration of the paper coated therewith, impairing the storage qualities or shelf life of the product.
  • the acid stabilizers employed in accordance with the invention are those conventionally used in two-component diazotype materialsfor example citric acid, tartaric acid, acetic acid and the like. These are used together with conventional light-sensitive diazonium compounds, as for example those referred to in US. Patent 2,501,874 and in the article by Van der Grinten in Photographic Journal, volume 92B (1952) page 46.
  • Preferred diazonium compounds are those derived from N-monoor N,N-disubstituted-p-phenylenediamine, as for example:
  • Azocoupling components suitable for use in the sensitizing compositions of the invention are those commonly employed in two-component diazotype photoprinting materials, such as:
  • the quantity of the trichloroacetic acid salt employed in'the sensitizing composition should be such as to exceed the stoichiometric equivalent of the quantity of base required to neutralize the acid stabilizer present in the mixture.
  • a quantity of said salt from one to three times the stoichiometrical equivalent of the acid stabilizer is suitable.
  • the quantity of said salt exceeds the sum of the stoichiometric equivalent of the diazonium compound and of the acid stabilizers.
  • the proportions of the other components of the mixture are those conventionally used in diazotype sensitizing compositions.
  • the sensitizing composition is advantageously applied in the form of an aqueous solution as a coating to a base, especially paper or cellulosic materials such as regenerated cellulose and allowed to dry.
  • a base such as paper sensitized with a conventional twocomponent diazotype sensitizing composition can be treated e.g., by spraying or padding with an aqueous solution of the trichloroacetic acid salt, and then dried.
  • the trichl-oroacetate may be concentrated in the surface stratum of the sensitized layer so that the excess is sufficient to effect development of the image in that portion of the layer, even though underlying strata of the sensitized layer may lack sufficient trichloroacetate to effect development.
  • the material After exposure under an opaque pattern to actinic light the material can then be developed at temperatures ranging from about 100 C. to the scorching temperature of the paper. Temperatures from 120 C. to 200 C. are satisfactory.
  • the trichloroacetic acid salt decomposes, rendering the salt-forming alkali metal or ammonium moiety thereof available to neutralize the acid stabilizer, and thereby causing coupling of the diazonium salt with the azo coupling component.
  • Example I A sensitizing solution is prepared by combining the following ingredients: Water cc 60 Glycerin cc 5 Isopropyl alcohol cc 1 Citric acid g 5 Zinc chloride g 5 N-beta-hydroxyethyl-N'-allyl-thiourea g- 2.5 2,3-dihydroxynaphthalene-6-s-odium sulfonate g 4 4-N,N-diethylaminobenzene diazonium chloride-zinc chloride double salt g 2 Saponin g 0.1 Sodium trichloroacetate g 12 Finely divided silica (1-5 microns) g 6 Water to make cc 100 This solution is coated on high grade sulfite bond paper, and dried. After exposure of the sensitized material to actinic light under an opaque pattern on a translucent supporting sheet, the sensitized material is heated to a temperature of about 120 C. An azo dye image is rapidly formed, reproducing the pattern of the original.
  • Example II Sulfite bond paper is coated with a sensitizing solution having the following composition:
  • Example III A paper base coated with a sensitizing solution having the following composition:
  • Example IV Paper preooated with an aqueous suspension of colloidal silica and then dried, as sensitized by coating with a sensitizing composition having the following ingredients:
  • the resulting material is dried and exposed under a pattern to actinic light. On heating to 130 C. an image is rapidly formed, reproducing the pattern.
  • the other ingredients of said compositions can be combined and applied to a supporting sheet and dried, yielding a two-component diazotype sensitized sheet of the kind heretofore used for ammonia development.
  • An aqueous solution of alkali metal or ammonium trichloroacetate having, for example, a concentration of 1020%, can then be applied to the sensitized surface of the sheet by atomizing, padding or the like, and the sheet again dried.
  • the surface portion of the lightsensitive layer includes the trichloroacetate salt in a quantity exceeding the stoichiometric equivalent of base required to neutralize the acid stabilizer in the same portion of the layer, even though the total quantity of acid stabilizer contained in the surface layer and underlying layer may exceed the stoichiometric equivalent to the trichloroacetate.
  • the material thus sensitized can be developed after exposure to actinic light under an opaque pattern, by heating to a temperature above 100 C., causing decomposition of the trichloroacetate with generation of sufiicient alkaline reacting residue to cause imagewise coupling of the two-component diazotype composition in the surface portions of the light-sensitive layer.
  • neutral salts of other bases which are themselves otherwise unreactive or inert toward the ingredients of the sensitizing composition can be used, e.g., the other alkali metal salts, alkaline earth metal salts and nitrogen base salts, trichloroacetates of mono-, diand tri-ethanolamine, or of triethylenetetramine, benzylamine or trimethylamine.
  • a sensitizing composition for diazotype photoprinting material comprising, in aqueous medium, an azo coupling component, a light-sensitive diazonium salt, an acid stabilizer against coupling, all such stabilizers of the composition having a dissociation constant at 25 C.
  • a neutral saltof trichloroacetic acid selected from the class consisting of sodium, potassium and ammonium salts, in an amount exceeding the stoichiometric equivalent of the amount of base required to neutralize said acid stabilizer.
  • Light-sensitive diazotype photoprinting material comprising a supporting sheet having thereon a light-sensitive surface layer comprising an azo coupling component, a light-sensitive diazonium salt, an acid stabilizer against coupling, all such stabilizers of said layer having a dissociation constant at 25 C. within the range of 10 to the 10 and a neutral trichloroacetic acid salt of the class consisting of sodium, potassium and ammonium salts, the amount of said salt in at least the surface portion of said layer exceeding the 'stoichiometric equivalent of the (3 amount of base required to neutralize the acid stabilizer in said surface portion of said layer.
  • Light-sensitive diazotype photoprinting material as defined in claim 6, wherein said light-sensitive diazonium salt is a zinc chloride double salt derived from a diazotized N-substituted p-phenylenediamine.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • General Physics & Mathematics (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
US284364A 1963-05-31 1963-05-31 Light-sensitive two-component diazotype materials adapted for heat development Expired - Lifetime US3326686A (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
US284364A US3326686A (en) 1963-05-31 1963-05-31 Light-sensitive two-component diazotype materials adapted for heat development
US292114A US3166422A (en) 1963-05-31 1963-07-01 Diazotype heat development photographic paper comprising a sugar brightening agent
US292066A US3294534A (en) 1963-05-31 1963-07-01 Diazotype photoprinting material susceptible to thermal development
US292115A US3255011A (en) 1963-05-31 1963-07-01 Two-component diazotype photoprinting material susceptible to thermal development
US292098A US3298834A (en) 1963-05-31 1963-07-01 Diazotype photoprinting material susceptible to thermal development
US292097A US3301679A (en) 1963-05-31 1963-07-01 Two-component diazotype light-sensitive photoprinting material susceptible to thermal development
GB21014/64A GB1063132A (en) 1963-05-31 1964-05-21 Improvements in or relating to light-sensitive two-component diazotype materials adapted for heat development
NL6406013A NL6406013A (enrdf_load_stackoverflow) 1963-05-31 1964-05-28
BE648593D BE648593A (enrdf_load_stackoverflow) 1963-05-31 1964-05-29
FR976481A FR1405427A (fr) 1963-05-31 1964-05-29 Matériaux du type diazo à deux composants, photosensibles pour développement thermique

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US284364A US3326686A (en) 1963-05-31 1963-05-31 Light-sensitive two-component diazotype materials adapted for heat development
US292114A US3166422A (en) 1963-05-31 1963-07-01 Diazotype heat development photographic paper comprising a sugar brightening agent
US292066A US3294534A (en) 1963-05-31 1963-07-01 Diazotype photoprinting material susceptible to thermal development
US292115A US3255011A (en) 1963-05-31 1963-07-01 Two-component diazotype photoprinting material susceptible to thermal development
US292098A US3298834A (en) 1963-05-31 1963-07-01 Diazotype photoprinting material susceptible to thermal development
US292097A US3301679A (en) 1963-05-31 1963-07-01 Two-component diazotype light-sensitive photoprinting material susceptible to thermal development

Publications (1)

Publication Number Publication Date
US3326686A true US3326686A (en) 1967-06-20

Family

ID=27559573

Family Applications (6)

Application Number Title Priority Date Filing Date
US284364A Expired - Lifetime US3326686A (en) 1963-05-31 1963-05-31 Light-sensitive two-component diazotype materials adapted for heat development
US292098A Expired - Lifetime US3298834A (en) 1963-05-31 1963-07-01 Diazotype photoprinting material susceptible to thermal development
US292115A Expired - Lifetime US3255011A (en) 1963-05-31 1963-07-01 Two-component diazotype photoprinting material susceptible to thermal development
US292066A Expired - Lifetime US3294534A (en) 1963-05-31 1963-07-01 Diazotype photoprinting material susceptible to thermal development
US292114A Expired - Lifetime US3166422A (en) 1963-05-31 1963-07-01 Diazotype heat development photographic paper comprising a sugar brightening agent
US292097A Expired - Lifetime US3301679A (en) 1963-05-31 1963-07-01 Two-component diazotype light-sensitive photoprinting material susceptible to thermal development

Family Applications After (5)

Application Number Title Priority Date Filing Date
US292098A Expired - Lifetime US3298834A (en) 1963-05-31 1963-07-01 Diazotype photoprinting material susceptible to thermal development
US292115A Expired - Lifetime US3255011A (en) 1963-05-31 1963-07-01 Two-component diazotype photoprinting material susceptible to thermal development
US292066A Expired - Lifetime US3294534A (en) 1963-05-31 1963-07-01 Diazotype photoprinting material susceptible to thermal development
US292114A Expired - Lifetime US3166422A (en) 1963-05-31 1963-07-01 Diazotype heat development photographic paper comprising a sugar brightening agent
US292097A Expired - Lifetime US3301679A (en) 1963-05-31 1963-07-01 Two-component diazotype light-sensitive photoprinting material susceptible to thermal development

Country Status (4)

Country Link
US (6) US3326686A (enrdf_load_stackoverflow)
BE (1) BE648593A (enrdf_load_stackoverflow)
GB (1) GB1063132A (enrdf_load_stackoverflow)
NL (1) NL6406013A (enrdf_load_stackoverflow)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3522048A (en) * 1965-12-09 1970-07-28 Gaf Corp Two-component heat developing diazotypes
US3529964A (en) * 1966-01-14 1970-09-22 L L Ridgway Enterprises Inc Heat developable diazo compositions and diazotype reproduction media
US3539345A (en) * 1967-02-01 1970-11-10 Gaf Corp Thermal diazotype papers
US3642483A (en) * 1966-11-07 1972-02-15 Ricoh Kk Thermally developable diazotype copying materials
US3650750A (en) * 1968-12-28 1972-03-21 Ricoh Kk Heat-developable diazo-type light-sensitive material
US3944422A (en) * 1969-09-01 1976-03-16 Mita Industrial Company Limited Photosensitive material in use for diazo-type multicolor reproduction

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1377476A (fr) * 1963-09-24 1964-11-06 Bauchet & Cie Ets Procédé de fabrication de feuilles héliographiques et articles analogues pour la reproduction de documents par diazotypie et feuilles photo-sensibles réalisées par la mise en oeuvre de ce procédé
US3300471A (en) * 1964-01-02 1967-01-24 Universal Oil Prod Co p-(nu-cyanoalkyl-nu-hydrocarbylamino)-benzenediazonium chlorides
US3536490A (en) * 1964-04-28 1970-10-27 Pitney Bowes Inc Novel diazotype copying process
US3408192A (en) * 1964-06-10 1968-10-29 Ibm Light-sensitive diazotype compositions and elements
US3389995A (en) * 1964-09-15 1968-06-25 Gen Aniline & Film Corp Two-component heat developable diazotypes containing amidine compounds
US3420666A (en) * 1964-10-15 1969-01-07 Gaf Corp Two-component heat developing diazotypes
US3389996A (en) * 1964-10-15 1968-06-25 Gen Aniline & Film Corp Two-component heat developable diazotypes
US3431109A (en) * 1964-10-16 1969-03-04 Addressograph Multigraph Heat sensitive diazotype materials
US3525618A (en) * 1964-12-04 1970-08-25 Geigy Ag J R Diazotype film materials
USB417241I5 (enrdf_load_stackoverflow) * 1964-12-09
US3406072A (en) * 1964-12-21 1968-10-15 Gaf Corp One-component diazotypes
US3409455A (en) * 1965-01-04 1968-11-05 Gaf Corp Process of reproduction on benzene diazonium fluoborate sheet by heat exposure
US3379531A (en) * 1965-03-30 1968-04-23 Gen Aniline & Film Corp Two-component heat developing diazotypes
DE1572155A1 (de) * 1965-08-10 1970-01-02 Dr Eduard Roell Licht-bzw.strahlungsempfindliches Material und Verfahren zu dessen Herstellung
NL6800539A (enrdf_load_stackoverflow) * 1968-01-12 1969-07-15
US3779758A (en) * 1969-03-25 1973-12-18 Photocircuits Corp Photosensitive process for producing printed circuits employing electroless deposition
US3793030A (en) * 1971-09-02 1974-02-19 Ricoh Kk Process for producing diazotype light-sensitive material
US3900324A (en) * 1972-06-25 1975-08-19 Ozalid Co Ltd Treatment of synthetic polyester film products
GB1488005A (en) * 1974-01-25 1977-10-05 Ici Ltd Diazotype materials
US4168171A (en) * 1977-08-05 1979-09-18 Minnesota Mining And Manufacturing Company Light-sensitive thermal developable diazotype sheets with imidazoles
US4230789A (en) * 1978-03-13 1980-10-28 Minnesota Mining And Manufacturing Company Thermal diazotype sheets
FR2455303A1 (fr) * 1979-04-24 1980-11-21 Rhone Poulenc Syst Procede pour la fabrication d'une carte d'identification inviolable comportant des photographies et carte obtenue selon ce procede
FR2470984B1 (fr) * 1979-11-28 1986-06-13 Schaeffer Andre Materiau diazotype developpable par la vapeur, l'eau ou la chaleur
BR8107605A (pt) * 1981-11-23 1983-07-05 Oce Nederland Bv Material de diazotipia
JPS5898729A (ja) * 1981-12-08 1983-06-11 Ricoh Co Ltd 熱現像型ジアゾ複写材料の製造方法
US4478926A (en) * 1981-12-28 1984-10-23 Andrews Paper & Chemical Co., Inc. Zinc sulfonates and their use in diazotypy
JPS58143336A (ja) * 1982-02-19 1983-08-25 Ricoh Co Ltd 熱現像型ジアゾ複写材料
US4508808A (en) * 1982-11-12 1985-04-02 Xidex Corporation Method of using diazotype photographic materials with preexposure treatment to form uniform sites of refractive index change

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2653091A (en) * 1950-01-31 1953-09-22 Rca Corp Photographic diazotype composition and heat development thereof
FR1249913A (fr) * 1959-11-23 1961-01-06 Bauchet & Cie Ets Produit diazotype développable par la chaleur
GB861601A (en) * 1957-07-26 1961-02-22 Napier & Son Ltd Control mechanism for aircraft power plants comprising a gas turbine engine driving a propeller
US3046128A (en) * 1958-07-03 1962-07-24 Dietzgen Co Eugene Thermally developable diazotype photoprinting material and production thereof
US3220846A (en) * 1960-06-27 1965-11-30 Eastman Kodak Co Use of salts of readily decarboxylated acids in thermography, photography, photothermography and thermophotography

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB816601A (en) * 1954-07-09 1959-07-15 Arnold Tanenbaum Improvements in or relating to diazotype processes
FR750080A (fr) * 1932-04-27 1933-08-03 Procédé de préparation de couches sensibles à la lumière
NL71256C (enrdf_load_stackoverflow) * 1948-10-01
US2727820A (en) * 1952-04-29 1955-12-20 Gen Aniline & Film Corp Light-sensitive diazotype layers containing carboxamides
US2807545A (en) * 1952-07-18 1957-09-24 Dick Co Ab Process of applying a diazotype photoprinting material to a base and the resultant article
US2732299A (en) * 1952-07-22 1956-01-24 Light sensitive
GB815005A (en) * 1957-07-03 1959-06-17 Ilford Ltd Improvements in or relating to radiation-sensitive diazotype materials
FR1255950A (fr) * 1959-11-23 1961-03-17 Bauchet Et Cie Ets Nouveau produit diazotype développable par la chaleur
US3102812A (en) * 1960-11-16 1963-09-03 Gen Aniline & Film Corp Stabilizers for one-component diazotype materials
NL270841A (enrdf_load_stackoverflow) * 1961-11-02
US3157503A (en) * 1963-03-19 1964-11-17 Keuffel & Esser Co Diazotype reproduction materials

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2653091A (en) * 1950-01-31 1953-09-22 Rca Corp Photographic diazotype composition and heat development thereof
GB861601A (en) * 1957-07-26 1961-02-22 Napier & Son Ltd Control mechanism for aircraft power plants comprising a gas turbine engine driving a propeller
US3046128A (en) * 1958-07-03 1962-07-24 Dietzgen Co Eugene Thermally developable diazotype photoprinting material and production thereof
FR1249913A (fr) * 1959-11-23 1961-01-06 Bauchet & Cie Ets Produit diazotype développable par la chaleur
US3220846A (en) * 1960-06-27 1965-11-30 Eastman Kodak Co Use of salts of readily decarboxylated acids in thermography, photography, photothermography and thermophotography

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3522048A (en) * 1965-12-09 1970-07-28 Gaf Corp Two-component heat developing diazotypes
US3529964A (en) * 1966-01-14 1970-09-22 L L Ridgway Enterprises Inc Heat developable diazo compositions and diazotype reproduction media
US3642483A (en) * 1966-11-07 1972-02-15 Ricoh Kk Thermally developable diazotype copying materials
US3539345A (en) * 1967-02-01 1970-11-10 Gaf Corp Thermal diazotype papers
US3650750A (en) * 1968-12-28 1972-03-21 Ricoh Kk Heat-developable diazo-type light-sensitive material
US3944422A (en) * 1969-09-01 1976-03-16 Mita Industrial Company Limited Photosensitive material in use for diazo-type multicolor reproduction

Also Published As

Publication number Publication date
US3166422A (en) 1965-01-19
US3294534A (en) 1966-12-27
US3255011A (en) 1966-06-07
US3298834A (en) 1967-01-17
GB1063132A (en) 1967-03-30
BE648593A (enrdf_load_stackoverflow) 1964-09-16
US3301679A (en) 1967-01-31
NL6406013A (enrdf_load_stackoverflow) 1964-12-01

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Owner name: R Q O HOLDING COMPANY INC 111 WEST 2ND ST JAMESTOW

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:GAF CORPORATION;REEL/FRAME:004006/0585

Effective date: 19820526

Owner name: R Q O HOLDING COMPANY INC, NEW YORK

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:GAF CORPORATION;REEL/FRAME:004006/0585

Effective date: 19820526