US3024362A - Heat sensitive reproduction material and mbthod of using same - Google Patents

Heat sensitive reproduction material and mbthod of using same Download PDF

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Publication number
US3024362A
US3024362A US827426A US82742659A US3024362A US 3024362 A US3024362 A US 3024362A US 827426 A US827426 A US 827426A US 82742659 A US82742659 A US 82742659A US 3024362 A US3024362 A US 3024362A
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United States
Prior art keywords
heat sensitive
sensitive layer
amino
original
heat
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Expired - Lifetime
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US827426A
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English (en)
Inventor
Sus Oskar
Glos Martin
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Kalle GmbH and Co KG
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Kalle GmbH and Co KG
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
    • B41M5/323—Organic colour formers, e.g. leuco dyes

Definitions

  • the principal object of'the present invention is an improved heat sensitive reproduction-material.
  • FIGURE 1 is an elevation of the heat sensitive mate-- rial under the original document with the heat sensitive
  • FIGURE 5 is a flow diagram showing the steps in the manufacture of the heat sensitive material.
  • The. new heat sensitive reproduction materials of the present invention contain in the heat sensitive layer a polyketo-hydrindene in combination with an amino carboxylic acid or a salt formed by the-reaction of a primary amine with an organic carboxylic acid or sulfonic acid. Under the influence of heat the polyketo-hydrindene reacts with the amine salt or the amino carboxylic acid to form a dyestulf which is probably analogous to a Schiflfbasc.
  • Polyketo-hyd'rindenes which are useful in accord with v the present invention include for example:
  • Acetic acid Substituted acetic acids such as Chloro acetic acid Bromo acetic acid Cyano acetic acid Phenyl acetic acid Bromo propionic acid Cinnamic acid Maionic acid Benzoic acid usNaphthalenesulfonic acid 4-toluene-sulfonic acid ice Examples of amino-carboxylic acids'are:
  • fl-(3'-aminophenyl)-propionic acid 4-amino-benzoic acid ages do not change their color nor do their contrasts decrease in quality,:so'that they can be stored for longer periods.
  • the heat sensitive layers of the present invention may be obtained from a coating composition which is prepared as follows:
  • the polyketo-hydrindenes and the amine salts or amino 9 carboxylic acids are mixed in the form of fine suspen- The mixture.
  • drying is elfected at room temperature, without heating.
  • the drying process may be speeded up by passing an air current over the'coated side of the sheet. Moderate heating of the layer or the air current may be considered, but the temperature applied should not exceed 35-40 C.
  • a salt of a primary amine it need not be isolated before its application. Also layers of equally high quality are obtained when the amine and the acid component are dispersed separately in the coating solution.
  • J maleic resins, such as the KM- and KPM-resins of J Messrs; Badische Anilinund Sodafabrik A.G., Ludwigshafen, Western Germany, and modified rosin esters, such as the product also sold by Messrs. Badische Anilinund Sodafabrik AG, Ludwigsha'fen, under the registered trademark Laropal" B.
  • the quantity of resin present in layer may also vary and de-' oaths kind of resin alsed. lngeneral, the quantity of the resin should amount to about half of the quantity of the amino component present.
  • Suitable base sheet materials for the heat sensitive reproduction layers of the present invention are: glass, paper, transparent paper, cellulose hydrate films, transparent plastic films, e.g. polyvinylchloride films, cellulose acetate films and polyethylene terephthalate films and other solid substances in the form of films or plates which are preferably permeable to light rays.
  • the heat sensitive reproduction materials of the present invention may be used according to either of the following processes:
  • the material provided with a heat sensitive layer is placed with its coated side in contact with the original to be copied, which may be an original having a written or printed image on one or both sides.
  • radiant heat is applied to the heat sensitive layer, e.g. by means of an infra-red lamp.
  • a deeply colored, direct, reversed image of the original is produced in the heat sensitive layer, which may be read from the back. of the transparent base material as a right reading image.
  • the duration of the heat action which is required for the production of faultless, sharp images, that are rich in contrast cannot be generally stated, but must be determined in each case. It depends on a number of factors, such as the kind and intensity of the source of energy used, its distance from the original, the kind of base material and the composition of the heat sensitive layer.
  • the reproduction material of the present invention may also be used for the production of images by means of a heated image forming member such as a heated stylus or stamp.
  • the coated transparent paper is placed with its coated side incontact with the original to be copied, e.g. a printed page of a book and then the back of the transparent paper is exposed to the radiations of a powerful infra-red lamp.
  • the infrared radiations penetrate through the uncoated side of the heat sensitive copying paper and are strongly absorbed by the printed areas of the original.
  • the heat thus absorbed causes a change in color in those parts of the heat sensitive layer which are in contact with the printed areas of the original.
  • a reversed directimage of the original in a dark blue color is obtained which is readable from the back of the transparent paper as a right reading image.
  • the heat sensitive layer contains a mixture of anhydro-bis-l.B-diltetohydrindene, 4,4- diamino-diphenylmethane and tit-naphthalene sulphonic acid brownish black copies are obtained.
  • the color of the heat sensitive layer turns from a light brown to dark brown, which within a short time becomes a brownish black.
  • the heat sensitive layer contains benzylamine 4-toluene-sulfonate as the second dye-forming component.
  • the conventional writing device of a recording apparatus e.g. a pressure indicator, a temperature recorder or a steam gauge
  • a recording needle which is electrically heated to the above referred temperature
  • a recording paper coated with a layer having the composition described in the preceding paragraph is used, the apparatus traces the measured values in a red-violet color on a light yellow background.
  • a heat sensitive reproduction material comprising a base sheet coated with a heat sensitive layer including a polyketohydrindene and a substance selected from the group consisting of amino carboxylic acids, salts formed from primary amines and organic carboxylic acids and salts formed from primary amines and sulfonic acids.
  • a heat sensitive reproduction material comprising a base sheet coated with a heat sensitive layer including a binding agent, a polyketohydrindene and a substance selected from the group consisting of amino carboxylic acids, salts formed from primary amines and organic carboxylic acids and salts formed from primary amines and sulfonic acids.
  • a heat sensitive reproduction material comprising atransparent base sheet coated with a heat sensitive layer including a polyketohydrindene and a substance selected from the group consisting of amino carboitylic acids, salts formed from primary amines and organic carboxylic acids and salts formed from primary amines and sulfonic acids.
  • a heat sensitive reproduction material comprising a base sheet coated with a heat sensitive layer including anhydro-bis-1,3-diketohydrindene and toluideine chloroacetate.
  • a heat sensitive reproduction material comprising a base sheet coated with a heat sensitive layer including bromoanhydro-bis-l,3-diketohydrindene and benzylamine chloroacetate.
  • a heat sensitive reproduction material comprising a base sheet coated with a heat sensitive layer including 1,2,3-triketohydrindene and 4-arnino-l-ethoxy-benzene chloroacetate.
  • a heat sensitive reproduction material comprising a base sheet coated with a heat sensitive layer including 1,2- diketohydrindene and ,6-(3'-aminophenyl)-propionic acid.
  • a heat sensitive reproduction material comprising a base sheet coated with a heat sensitive layer including 1,2, 3-triketohydrindene and benzylamine malonate.
  • the method of making reproductions comprising placing a transparent base sheet coated with a heat sensitive layer including a polyketohydrindene and a substance selected from the group consisting of amino carboxylic acids, salts formed from primary amines and organic carboxylic acids and salts formed from primary amines and sulfonic acids with its coated side in contact with an original to be copied and applying radiant heat through said transparent base sheet to form an image of the original in said heat sensitive layer.
  • the method of making reproductions comprising placing a base sheet coated with a heat sensitive layer including a polyketohydrindene and a substance selected from the group consisting of amino carboxylic acids, salts formed from primary amines and organic carboxylic acids and salts formed from primary amines and sulfonic acids in contact with an original to be copied and applying radiant heat through said original to form an image of said original in said heat sensitive layer.
  • a heat sensitive layer including a polyketohydrindene and a substance selected from the group consisting of amino carboxylic acids, salts formed from primary amines and organic carboxylic acids and salts formed from primary amines and sulfonic acids
  • the method of forming an image comprising bringing a heated image forming member into contactwith a heat sensitive layer including a polyketohydrindene and a substance selected from the group consisting of amino carboxylic acids, salts formed from primary amines and organic carboxylic acids and salts formed from primary amines and sulfonic acids coated on a base sheet in contact with an original to be copied.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
US827426A 1958-08-09 1959-07-16 Heat sensitive reproduction material and mbthod of using same Expired - Lifetime US3024362A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEK35503A DE1109712B (de) 1958-08-09 1958-08-09 Kopierschichten zur Herstellung von Bildern durch Waerme

Publications (1)

Publication Number Publication Date
US3024362A true US3024362A (en) 1962-03-06

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US827426A Expired - Lifetime US3024362A (en) 1958-08-09 1959-07-16 Heat sensitive reproduction material and mbthod of using same

Country Status (4)

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US (1) US3024362A (de)
DE (1) DE1109712B (de)
FR (1) FR1240124A (de)
GB (1) GB905215A (de)

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3129109A (en) * 1961-09-25 1964-04-14 Minnesota Mining & Mfg Heat-sensitive copy-sheet
US3149991A (en) * 1962-01-05 1964-09-22 Nashua Corp Heat developable paper
US3149993A (en) * 1962-01-18 1964-09-22 Nashua Corp Heat developable paper
US3161770A (en) * 1962-03-20 1964-12-15 Dietzgen Co Eugene Thermographic reproduction paper and method of using
US3162763A (en) * 1962-04-05 1964-12-22 Dietzgen Co Eugene Thermographic reproduction paper, method of making and method of using
US3166433A (en) * 1962-08-01 1965-01-19 Nashua Corp Heat sensitive copy and recording sheet
US3167444A (en) * 1962-11-19 1965-01-26 Nashua Corp Heat responsive marking sheets
US3167445A (en) * 1962-06-29 1965-01-26 Nashua Corp Heat responsive marking sheets
US3167651A (en) * 1962-05-15 1965-01-26 Dietzgen Co Eugene Thermographic reproduction paper and method of making and using
US3174038A (en) * 1962-06-18 1965-03-16 Dietzgen Co Eugene Thermographic reproduction paper and method of using
US3185584A (en) * 1962-11-19 1965-05-25 Nashua Corp Heat responsive marking sheets
US3185585A (en) * 1962-11-19 1965-05-25 Nashua Corp Heat responsive marking sheets
US3185583A (en) * 1962-11-19 1965-05-25 Nashua Corp Heat responsive marking sheets
US3293061A (en) * 1963-11-21 1966-12-20 Man Res Lab Inc Primary amine modified secondary or tertiary amine-polyketo reaction product in a heat developable copy sheet
US3301697A (en) * 1960-12-02 1967-01-31 Robert B Russell Thermographic transfer sheet having a support of a paper and plastic coating and the method of use
US3770442A (en) * 1971-10-15 1973-11-06 Minnesota Mining & Mfg Stabilized light-sensitive intermediate sheet
US4061836A (en) * 1976-04-13 1977-12-06 Bard Laboratories, Inc. Thermographic recording system
US4061831A (en) * 1976-04-13 1977-12-06 Bard Laboratories, Inc. Thermal recording system
US4082555A (en) * 1976-08-18 1978-04-04 Eastman Kodak Company Photothermographic materials and process
US4111703A (en) * 1977-02-25 1978-09-05 Graphic Controls Corporation Heat-sensitive coating composition with 4-aromatic and hydroxy substituted piperidine derivative and cyclic polyketo compound
FR2382337A1 (fr) * 1977-03-04 1978-09-29 Lawton William Compositions d'enregistrement sensibles a la chaleur, comprenant un revetement a base de produits de condensation de composes diimino heterocycliques et d'aldehydes aromatiques, et de composes polycetoniques cycliques

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2663654A (en) * 1952-05-15 1953-12-22 Minnesota Mining & Mfg Heat-sensitive copying paper
US2680062A (en) * 1949-07-23 1954-06-01 Keuffel & Esser Co Process for the production of azo dyestuff images
US2732286A (en) * 1953-09-30 1956-01-24 Propstl
US2859351A (en) * 1951-02-02 1958-11-04 Minnesota Mining & Mfg Method of making permanent facsimile copies
US2899334A (en) * 1958-05-19 1959-08-11 Heat-sensitive layer
US2910377A (en) * 1956-06-28 1959-10-27 Minnesota Mining & Mfg Heat-sensitive copying-paper
US2919349A (en) * 1956-04-02 1959-12-29 Minnesota Mining & Mfg Shadow thermoprinting
US2962382A (en) * 1958-02-25 1960-11-29 Ludlow Corp Sheet recording material and method of making same
US2967785A (en) * 1959-08-14 1961-01-10 Eastman Kodak Co Thermographic copying material

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2680062A (en) * 1949-07-23 1954-06-01 Keuffel & Esser Co Process for the production of azo dyestuff images
US2859351A (en) * 1951-02-02 1958-11-04 Minnesota Mining & Mfg Method of making permanent facsimile copies
US2663654A (en) * 1952-05-15 1953-12-22 Minnesota Mining & Mfg Heat-sensitive copying paper
US2732286A (en) * 1953-09-30 1956-01-24 Propstl
US2919349A (en) * 1956-04-02 1959-12-29 Minnesota Mining & Mfg Shadow thermoprinting
US2910377A (en) * 1956-06-28 1959-10-27 Minnesota Mining & Mfg Heat-sensitive copying-paper
US2962382A (en) * 1958-02-25 1960-11-29 Ludlow Corp Sheet recording material and method of making same
US2899334A (en) * 1958-05-19 1959-08-11 Heat-sensitive layer
US2967785A (en) * 1959-08-14 1961-01-10 Eastman Kodak Co Thermographic copying material

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3301697A (en) * 1960-12-02 1967-01-31 Robert B Russell Thermographic transfer sheet having a support of a paper and plastic coating and the method of use
US3129109A (en) * 1961-09-25 1964-04-14 Minnesota Mining & Mfg Heat-sensitive copy-sheet
US3149991A (en) * 1962-01-05 1964-09-22 Nashua Corp Heat developable paper
US3149993A (en) * 1962-01-18 1964-09-22 Nashua Corp Heat developable paper
US3161770A (en) * 1962-03-20 1964-12-15 Dietzgen Co Eugene Thermographic reproduction paper and method of using
US3162763A (en) * 1962-04-05 1964-12-22 Dietzgen Co Eugene Thermographic reproduction paper, method of making and method of using
US3167651A (en) * 1962-05-15 1965-01-26 Dietzgen Co Eugene Thermographic reproduction paper and method of making and using
US3174038A (en) * 1962-06-18 1965-03-16 Dietzgen Co Eugene Thermographic reproduction paper and method of using
US3167445A (en) * 1962-06-29 1965-01-26 Nashua Corp Heat responsive marking sheets
US3166433A (en) * 1962-08-01 1965-01-19 Nashua Corp Heat sensitive copy and recording sheet
US3185584A (en) * 1962-11-19 1965-05-25 Nashua Corp Heat responsive marking sheets
US3185585A (en) * 1962-11-19 1965-05-25 Nashua Corp Heat responsive marking sheets
US3185583A (en) * 1962-11-19 1965-05-25 Nashua Corp Heat responsive marking sheets
US3167444A (en) * 1962-11-19 1965-01-26 Nashua Corp Heat responsive marking sheets
US3293061A (en) * 1963-11-21 1966-12-20 Man Res Lab Inc Primary amine modified secondary or tertiary amine-polyketo reaction product in a heat developable copy sheet
US3770442A (en) * 1971-10-15 1973-11-06 Minnesota Mining & Mfg Stabilized light-sensitive intermediate sheet
US4061836A (en) * 1976-04-13 1977-12-06 Bard Laboratories, Inc. Thermographic recording system
US4061831A (en) * 1976-04-13 1977-12-06 Bard Laboratories, Inc. Thermal recording system
US4082555A (en) * 1976-08-18 1978-04-04 Eastman Kodak Company Photothermographic materials and process
US4111703A (en) * 1977-02-25 1978-09-05 Graphic Controls Corporation Heat-sensitive coating composition with 4-aromatic and hydroxy substituted piperidine derivative and cyclic polyketo compound
FR2382337A1 (fr) * 1977-03-04 1978-09-29 Lawton William Compositions d'enregistrement sensibles a la chaleur, comprenant un revetement a base de produits de condensation de composes diimino heterocycliques et d'aldehydes aromatiques, et de composes polycetoniques cycliques

Also Published As

Publication number Publication date
FR1240124A (fr) 1960-09-02
GB905215A (en) 1962-09-05
DE1109712B (de) 1961-06-29

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