EP0465403A1 - Druckempfindliches Aufzeichnungs- und Übertragungsmaterial - Google Patents

Druckempfindliches Aufzeichnungs- und Übertragungsmaterial Download PDF

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Publication number
EP0465403A1
EP0465403A1 EP91810368A EP91810368A EP0465403A1 EP 0465403 A1 EP0465403 A1 EP 0465403A1 EP 91810368 A EP91810368 A EP 91810368A EP 91810368 A EP91810368 A EP 91810368A EP 0465403 A1 EP0465403 A1 EP 0465403A1
Authority
EP
European Patent Office
Prior art keywords
material according
substituted
formula
lower alkyl
alkyl
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.)
Withdrawn
Application number
EP91810368A
Other languages
German (de)
English (en)
French (fr)
Inventor
René Graf
Werner Mischler
Peter Dr. Burri
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.)
Novartis AG
Original Assignee
Ciba Geigy AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of EP0465403A1 publication Critical patent/EP0465403A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • BPERFORMING OPERATIONS; TRANSPORTING
    • B41PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41MPRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00Duplicating or marking methods; Sheet materials for use therein
    • B41M5/124Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
    • B41M5/132Chemical colour-forming components; Additives or binders therefor
    • B41M5/136Organic colour formers, e.g. leuco dyes
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B41PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41MPRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00Duplicating or marking methods; Sheet materials for use therein
    • B41M5/124Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
    • B41M5/132Chemical colour-forming components; Additives or binders therefor
    • B41M5/136Organic colour formers, e.g. leuco dyes
    • B41M5/145Organic colour formers, e.g. leuco dyes with a lactone or lactam ring

Definitions

  • the present invention relates to a pressure-sensitive recording and transfer material which in a first sheet has a coating comprising one of components (A) and (B) or a solvent for these components and in a second sheet the other component or both components (A). and (B) and contains an electron attractive and color developing material as component (C), wherein (A) a polycyclic compound of the formula is what X is a monocyclic or polycyclic aromatic or heteroaromatic radical, Y is a substituent that can be split off as an anion Q2 -CH2-, -CO-, -CS- or -SO2- and R is hydrogen, C1-C12-alkyl, C5-C10-cycloalkyl, aryl, such as phenyl or aralkyl, such as benzyl and the ring A is an aromatic or heterocyclic radical with 6 ring atoms, which may have an aromatic fused ring, both the ring A and the fused ring can be substituted and (B) represents an organic condensation
  • Components (A), (B) and (C) come into contact with each other by pressure and leave records on the developer sheet.
  • the color is produced in accordance with the type of components (A) and (B), which represent the electron donor and form the chromogenic part.
  • the color formation is caused by component (C).
  • you can the desired colors, such as yellow, orange, red, violet, blue, green, gray, black or mixed colors are generated.
  • Lower alkyl, lower alkoxy and lower alkylthio are groups or group components which have 1 to 6, in particular 1 to 3, carbon atoms.
  • Examples of such groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, amyl, isoamyl or hexyl or methoxy, ethoxy, isopropoxy, isobutoxy, tert-butoxy or amyloxy or methylthio , Ethylthio, propylthio or butylthio.
  • the pair of substituents (R1 and R2) together with the common nitrogen atom represent a heterocyclic radical
  • this is, for example, pyrrolidino, piperidino, pipecolino, morpholino, thiomorpholino, piperazino, N-alkylpiperazino, such as e.g. N-methylpiperazino, N-phenylpiperazino or N-alkylimidazolino.
  • Preferred saturated heterocyclic radicals for -NR1R2 are pyrrolidino, piperidino or morpholino.
  • R1 and R2 are preferably cyclohexyl, benzyl, phenethyl, cyano-lower alkyl e.g. ⁇ -cyanoethyl or primarily lower alkyl, e.g. Methyl, ethyl or n-butyl.
  • -NR1R2 is also preferably pyrrolidinyl.
  • R3 is preferably lower alkyl or benzyl.
  • V can advantageously be hydrogen, halogen, lower alkyl, such as methyl, benzyloxy, C1-C8-alkoxy, primarily lower alkoxy, such as methoxy, ethoxy, isopropoxy or tert-butoxy, or the group -NT1T2, with the radicals being T1 and T2 is preferably C1-C8 acyl or lower alkyl and the other is hydrogen or lower alkyl.
  • the acyl radical in this case is especially lower alkylcarbonyl, such as acetyl or Propionyl.
  • V is preferably acetylamino, dimethylamino, diethylamino, benzyloxy or especially lower alkoxy and especially ethoxy or hydrogen.
  • acyloxy groups include acetyloxy, propionyloxy, chloroacetyloxy, trimethylacetyloxy, benzoyloxy, methylsulfonyloxy, ethylsulfonyloxy, chloroethylsulfonyloxy, trifluoromethylsulfonyloxy, 2-chloroethylsulfonylacetyloxy, phenylsulfonyloxy, tolylsulfonyloxy, tolylsulfonyloxyyl, tolylsulfonyloxyyl and tolylsulfonyloxyyl.
  • Lactone compounds of the formula are also particularly preferred wherein D and Y2 have the meaning given in formula (3) and R7, R8 and R9 each represent lower alkyl and in particular ethyl or n-butyl.
  • Particularly preferred condensation components are anilines, such as cresidines, phenetidines or N, N-di-lower alkylanilines, 2-lower alkyls, 3-lower alkyls or 2-phenyl indoles, which can each be N-substituted by C1-C8-alkyl and 5-pyrazolones.
  • Further preferred coupling components are 3-lower alkyl-6-lower alkoxy- or -6-di-lower alkylaminoindoles, which can also each be N-substituted by C1-C8-alkyl.
  • Solid carboxylic acids advantageously aliphatic dicarboxylic acids, such as, for example, tartaric acid, oxalic acid, maleic acid, citric acid, citraconic acid or succinic acid, and alkylphenol acetylene resin, maleic acid-rosin resin, carboxypolymethylene or a partially or fully hydrolyzed polymer of styrene ether, ethylene or vinyl with maleic acid, ethylene or vinyl ether with vinyl ether or anhydride will.
  • aliphatic dicarboxylic acids such as, for example, tartaric acid, oxalic acid, maleic acid, citric acid, citraconic acid or succinic acid, and alkylphenol acetylene resin, maleic acid-rosin resin, carboxypolymethylene or a partially or fully hydrolyzed polymer of styrene ether, ethylene or vinyl with maleic acid, ethylene or vinyl ether with vinyl ether or anhydride will.
  • the mixing ratio of component (C) to components (A) and (B) depends on the type of the three components, the type of color change and of course also on the desired color concentration. Satisfactory results are obtained when the color-developing component (C) is used in amounts of 0.1 to 100 parts by weight, preferably 1 to 20 parts by weight, per part of components (A) and (B).
  • suitable solvents are preferably non-volatile solvents, for example halogenated benzene, diphenyls or paraffin, such as, for example, chlorinated paraffin, trichlorobenzene, monochlorodiphenyl, dichlorodiphenyl or trichlorodiphenyl; Esters such as dibutyl adipate, dibutyl phthalate, dioctyl phthalate, butyl benzyl adipate, trichloroethyl phosphate, trioctyl phosphate, tricresyl phosphate; aromatic ethers such as benzylphenyl ether; Hydrocarbon oils, such as paraffin oil or kerosene, aromatic hydrocarbons, for example derivatives of benzene, diphenyl, naphthalene or terphenyl, alkylated with isopropyl, isobutyl, sec-butyl or tert-butyl,
  • the encapsulated component (A) is in the form of a layer on the back of a transfer sheet and component (B) and the electron acceptor (component (C)) are in the form of one or two individual layers on the front of a receiving sheet.
  • component (B) and the electron acceptor (component (C)) are in the form of one or two individual layers on the front of a receiving sheet.
  • the transfer sheet contains component (B) and component (A) and the electron acceptor (C) are present on the receiving sheet. Both arrangements can also be reversed.
  • the recording material according to the invention also comprises a carrier sheet, the back of which has encapsulated solvent for components (A) and (B), and a further sheet, the surface of which is coated with components (A), (B) and (C).
  • a carrier sheet the back of which has encapsulated solvent for components (A) and (B)
  • a further sheet the surface of which is coated with components (A), (B) and (C).
  • One of the components (A) and (B) or both can also be incorporated in the lower sheet (receiving sheet).
  • the CB sheet is placed on the CF sheet. Is by hand or with writing pressure on the paper on the typewriter, then a purple print appears.
  • the CB sheet is placed on the CF sheet. If pressure is exerted on the paper by hand or typewriter, a purple copy is created.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Indole Compounds (AREA)
  • Color Printing (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)
EP91810368A 1990-05-29 1991-05-14 Druckempfindliches Aufzeichnungs- und Übertragungsmaterial Withdrawn EP0465403A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH181290 1990-05-29
CH1812/90 1990-05-29

Publications (1)

Publication Number Publication Date
EP0465403A1 true EP0465403A1 (de) 1992-01-08

Family

ID=4219181

Family Applications (1)

Application Number Title Priority Date Filing Date
EP91810368A Withdrawn EP0465403A1 (de) 1990-05-29 1991-05-14 Druckempfindliches Aufzeichnungs- und Übertragungsmaterial

Country Status (3)

Country Link
US (1) US5244860A (ja)
EP (1) EP0465403A1 (ja)
JP (1) JPH04232090A (ja)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0082822A2 (de) * 1981-12-23 1983-06-29 Ciba-Geigy Ag Chromogene Dihydrofuropyridinone, Verfahren zu ihrer Herstellung und ihre Verwendung in druck- oder wärmeempfindlichen Aufzeichnungsmaterialien
US4688059A (en) * 1982-01-08 1987-08-18 The Hilton-Davis Chemical Co. Marking systems
EP0373110A2 (de) * 1988-12-02 1990-06-13 Ciba-Geigy Ag Druck- oder wärmeempfindliches Aufzeichnungsmaterial

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4508897A (en) * 1981-12-23 1985-04-02 Ciba Geigy Corporation Preparation of chromogenic azaphthalides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0082822A2 (de) * 1981-12-23 1983-06-29 Ciba-Geigy Ag Chromogene Dihydrofuropyridinone, Verfahren zu ihrer Herstellung und ihre Verwendung in druck- oder wärmeempfindlichen Aufzeichnungsmaterialien
US4688059A (en) * 1982-01-08 1987-08-18 The Hilton-Davis Chemical Co. Marking systems
EP0373110A2 (de) * 1988-12-02 1990-06-13 Ciba-Geigy Ag Druck- oder wärmeempfindliches Aufzeichnungsmaterial

Also Published As

Publication number Publication date
US5244860A (en) 1993-09-14
JPH04232090A (ja) 1992-08-20

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