GB2002801A - Chromogenic compounds for use as color formers in copying recording materials - Google Patents

Chromogenic compounds for use as color formers in copying recording materials

Info

Publication number
GB2002801A
GB2002801A GB7832576A GB7832576A GB2002801A GB 2002801 A GB2002801 A GB 2002801A GB 7832576 A GB7832576 A GB 7832576A GB 7832576 A GB7832576 A GB 7832576A GB 2002801 A GB2002801 A GB 2002801A
Authority
GB
United Kingdom
Prior art keywords
carbon atoms
alkyl
hydrogen
halogen
recording materials
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.)
Granted
Application number
GB7832576A
Other versions
GB2002801B (en
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.)
Yamada Chemical Co Ltd
Original Assignee
Yamada Chemical Co Ltd
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 Yamada Chemical Co Ltd filed Critical Yamada Chemical Co Ltd
Publication of GB2002801A publication Critical patent/GB2002801A/en
Application granted granted Critical
Publication of GB2002801B publication Critical patent/GB2002801B/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
    • 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
    • B41M5/124—Duplicating 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
    • B41M5/132—Chemical colour-forming components; Additives or binders therefor
    • B41M5/136—Organic colour formers, e.g. leuco dyes
    • B41M5/145—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
    • B41M5/1455—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring characterised by fluoran compounds
    • 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
    • B41M5/327—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
    • B41M5/3275—Fluoran compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/10—Spiro-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Color Printing (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Photoreceptors In Electrophotography (AREA)

Abstract

The chromogenic fluoran compounds of the invention are of the formula: <IMAGE> wherein R1 is alkyl of from five eight carbon atoms; R2 is alkyl of from one to eight carbon atoms, benzyl, cyclohexyl, phenyl or phenyl substituted by alkyl of from one to four carbon atoms, alkoxy of from one to four carbon atoms or halogen; R3 is enzyl; X1 and X2 are independently hydrogen or alkyl of from one to four carbon atoms, X3 is hydrogen, alkyl of from one to four carbon atoms, halogen or trifluoromethyl; and n is 1 or 2; providing that R1 does not represent amyl when R2 is alkyl of from 1 to five carbon atoms, X1 and X2 are each hydrogen, X3 is hydrogen, alkyl of from one to four carbon atoms or halogen. These compounds are particularly suitable for use in providing high quality pressure- or heat-sensitive copying sheets in which a color former, dissolved in an organic solvent, is microencapsulated on one surface of a sheet and a sheet coated with an electron-accepting substance is provided in operative association therewith.
GB7832576A 1977-08-08 1978-08-08 Chromogenic compounds for use as colour formers in copying or recording materials Expired GB2002801B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP9527077A JPS5434909A (en) 1977-08-08 1977-08-08 Colored recording material

Publications (2)

Publication Number Publication Date
GB2002801A true GB2002801A (en) 1979-02-28
GB2002801B GB2002801B (en) 1982-02-17

Family

ID=14133071

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7832576A Expired GB2002801B (en) 1977-08-08 1978-08-08 Chromogenic compounds for use as colour formers in copying or recording materials

Country Status (5)

Country Link
JP (1) JPS5434909A (en)
DE (1) DE2834711C2 (en)
FI (1) FI69859C (en)
FR (1) FR2400053A1 (en)
GB (1) GB2002801B (en)

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0048026A1 (en) * 1980-09-17 1982-03-24 Hodogaya Chemical Co., Ltd. Heat sensitive record sheet
FR2517599A1 (en) * 1981-12-09 1983-06-10 Ricoh Kk THERMOSENSIBLE RECORDING MATERIAL
EP0089752A2 (en) * 1982-02-24 1983-09-28 Kanzaki Paper Manufacturing Co., Ltd Fluoran derivatives, process for their preparation and their use in recording systems
EP0122318A2 (en) * 1983-04-14 1984-10-24 Hodogaya Chemical Co., Ltd. Heat sensitive record sheet
GB2141727A (en) * 1983-04-26 1985-01-03 Shin Nisso Kako Co Ltd Chromogenic fluoran recording materials
GB2154597A (en) * 1982-12-27 1985-09-11 Shin Nisso Kako Co Ltd Chromogenic recording materials
EP0155796A2 (en) * 1984-03-05 1985-09-25 Hodogaya Chemical Co., Ltd. 6-Tetrahydrofurfurylaminofluoran compound useful as a color former
EP0155593A2 (en) * 1984-03-09 1985-09-25 Kanzaki Paper Manufacturing Co., Ltd Fluoran compounds and recording sheets containing them
US4694088A (en) * 1984-03-24 1987-09-15 Hodogaya Chemical Co., Ltd. Fluoran compounds
EP0435149A2 (en) * 1989-12-25 1991-07-03 Yamamoto Chemicals, Inc. Method of producing 3-dibutylamino-6-methyl-7-anilinofluoran
EP0220515B1 (en) * 1985-10-08 1992-01-15 Showa Denko Kabushiki Kaisha Fluoran derivatives, process for preparation thereof and recording material containing the same
WO1999007793A1 (en) * 1997-08-04 1999-02-18 Nycomed Amersham Plc Dye intermediate and method to manufacture dyes
WO2006067073A1 (en) * 2004-12-24 2006-06-29 Ciba Specialty Chemicals Holding Inc. Coating compositions for marking substrates
WO2012160084A1 (en) 2011-05-25 2012-11-29 Tetra Laval Holdings & Finance S.A. Improved near infrared absorbers
WO2013098076A1 (en) 2011-12-30 2013-07-04 Tetra Laval Holdings & Finance S.A. Laminated color forming composition
US8853314B2 (en) 2008-10-23 2014-10-07 Datalase Ltd. Heat absorbing additives
US8900414B2 (en) 2007-11-07 2014-12-02 Datalase, Ltd. Fiber products
US9045619B2 (en) 2007-08-22 2015-06-02 Datalase Ltd. Laser-sensitive coating composition
US9982157B2 (en) 2008-10-27 2018-05-29 Datalase Ltd. Aqueous laser-sensitive composition for marking substrates
EP3950068A4 (en) * 2019-03-29 2022-12-14 The Pilot Ink Co., Ltd. Reversible thermochromic composition, reversible thermochromic microcapsule pigment comprising same, and writing instrument using same

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58162663A (en) * 1982-03-19 1983-09-27 Fuji Photo Film Co Ltd Fluoran derivative and recording material using the same
JPS5968373A (en) * 1982-10-13 1984-04-18 Shin Nisso Kako Co Ltd Fluoran compound
JPS5978886A (en) * 1982-10-28 1984-05-07 Shin Nisso Kako Co Ltd Chromogenic recording material
US4536220A (en) * 1982-12-27 1985-08-20 Kanzaki Paper Manufacturing Co., Ltd. Fluoran derivatives as new compounds and recording system utilizing the same as colorless chromogenic material
JPS59136349A (en) * 1983-01-25 1984-08-04 Yamada Kagaku Kogyo Kk Fluoran and color-developing recording material
JPS59138264A (en) * 1983-01-28 1984-08-08 Hodogaya Chem Co Ltd Fluoran compound
JPS59143682A (en) * 1983-02-07 1984-08-17 Nippon Kayaku Co Ltd Recording sheet
JPS6174883A (en) * 1984-09-20 1986-04-17 Taoka Chem Co Ltd Recording material
JPS61144387A (en) * 1984-12-19 1986-07-02 Taoka Chem Co Ltd Recording material
JPH0730256B2 (en) * 1985-06-05 1995-04-05 日本曹達株式会社 Fluoran-based coloring dye
JPS62294647A (en) * 1987-05-22 1987-12-22 Shin Nisso Kako Co Ltd Benzoic acid derivative
EP0410206B1 (en) * 1989-07-19 1994-09-28 MITSUI TOATSU CHEMICALS, Inc. Fluoran compounds, crystalline toluene adducts thereof, recording material comprising same and process for their preparation
US5231069A (en) * 1989-08-01 1993-07-27 Mitsui Toatsu Chemicals Inc. Fluoran compound, heat sensitive recording materials comprising fluoran compound
EP0411509B1 (en) * 1989-08-01 1994-09-28 MITSUI TOATSU CHEMICALS, Inc. Fluoran compound, process for preparation thereof and heat sensitive recording materials comprising said compound
DE69115410T2 (en) * 1990-09-17 1996-08-08 Mitsui Toatsu Chemicals Crystal of a fluoran compound, its manufacturing process and recording material containing the crystal
GB9414637D0 (en) 1994-07-20 1994-09-07 Wiggins Teape Group The Limite Presure-sensitive copying material
MX2009009394A (en) 2007-03-15 2009-09-11 Basf Se Heat-sensitive coating compositions based on resorcinyl triazine derivatives.
US9333786B2 (en) 2007-07-18 2016-05-10 Datalase, Ltd. Laser-sensitive coating formulations
US9267042B2 (en) 2008-10-27 2016-02-23 Datalase Ltd. Coating composition for marking substrates

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1306263A (en) * 1969-05-22 1973-02-07
GB1277545A (en) * 1969-05-23 1972-06-14 Fuji Photo Film Co Ltd Fluoran compounds and pressure-sensitive copying paper
JPS5033891B2 (en) * 1971-10-29 1975-11-04
JPS4862506A (en) * 1971-12-04 1973-08-31
JPS4875628A (en) * 1971-12-27 1973-10-12
JPS5435128B2 (en) * 1972-07-12 1979-10-31
JPS5138245B2 (en) * 1973-05-22 1976-10-20
JPS566875B2 (en) * 1974-09-24 1981-02-14

Cited By (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0048026A1 (en) * 1980-09-17 1982-03-24 Hodogaya Chemical Co., Ltd. Heat sensitive record sheet
FR2517599A1 (en) * 1981-12-09 1983-06-10 Ricoh Kk THERMOSENSIBLE RECORDING MATERIAL
EP0089752A2 (en) * 1982-02-24 1983-09-28 Kanzaki Paper Manufacturing Co., Ltd Fluoran derivatives, process for their preparation and their use in recording systems
EP0089752A3 (en) * 1982-02-24 1985-06-26 Kanzaki Paper Manufacturing Co., Ltd Fluoran derivatives, process for their preparation and their use in recording systems
GB2154597A (en) * 1982-12-27 1985-09-11 Shin Nisso Kako Co Ltd Chromogenic recording materials
EP0122318A2 (en) * 1983-04-14 1984-10-24 Hodogaya Chemical Co., Ltd. Heat sensitive record sheet
EP0122318A3 (en) * 1983-04-14 1985-01-09 Hodogaya Chemical Co., Ltd. Heat sensitive record sheet
GB2141727A (en) * 1983-04-26 1985-01-03 Shin Nisso Kako Co Ltd Chromogenic fluoran recording materials
US4597795A (en) * 1984-03-05 1986-07-01 Hodogaya Chemical Co., Ltd. 6-tetrahydrofurfurylaminofluoran compound useful as a color former
EP0155796A3 (en) * 1984-03-05 1986-04-02 Hodogaya Chemical Co., Ltd. 6-tetrahydrofurfurylaminofluoran compound useful as a color former
EP0155796A2 (en) * 1984-03-05 1985-09-25 Hodogaya Chemical Co., Ltd. 6-Tetrahydrofurfurylaminofluoran compound useful as a color former
EP0155593A2 (en) * 1984-03-09 1985-09-25 Kanzaki Paper Manufacturing Co., Ltd Fluoran compounds and recording sheets containing them
EP0155593A3 (en) * 1984-03-09 1986-02-26 Kanzaki Paper Manufacturing Co., Ltd Fluoran compounds and recording sheets containing them
US4694088A (en) * 1984-03-24 1987-09-15 Hodogaya Chemical Co., Ltd. Fluoran compounds
EP0220515B1 (en) * 1985-10-08 1992-01-15 Showa Denko Kabushiki Kaisha Fluoran derivatives, process for preparation thereof and recording material containing the same
EP0435149A2 (en) * 1989-12-25 1991-07-03 Yamamoto Chemicals, Inc. Method of producing 3-dibutylamino-6-methyl-7-anilinofluoran
EP0435149A3 (en) * 1989-12-25 1991-10-16 Yamamoto Chemicals, Inc. Method of producing 3-dibutyl-amino-6-methyl-7-anilinofluoran
WO1999007793A1 (en) * 1997-08-04 1999-02-18 Nycomed Amersham Plc Dye intermediate and method to manufacture dyes
WO2006067073A1 (en) * 2004-12-24 2006-06-29 Ciba Specialty Chemicals Holding Inc. Coating compositions for marking substrates
US8101544B2 (en) 2004-12-24 2012-01-24 Datalase Ltd. Coating compositions for marking substrates
US9045619B2 (en) 2007-08-22 2015-06-02 Datalase Ltd. Laser-sensitive coating composition
US8900414B2 (en) 2007-11-07 2014-12-02 Datalase, Ltd. Fiber products
US8853314B2 (en) 2008-10-23 2014-10-07 Datalase Ltd. Heat absorbing additives
US9982157B2 (en) 2008-10-27 2018-05-29 Datalase Ltd. Aqueous laser-sensitive composition for marking substrates
WO2012160084A1 (en) 2011-05-25 2012-11-29 Tetra Laval Holdings & Finance S.A. Improved near infrared absorbers
WO2013098076A1 (en) 2011-12-30 2013-07-04 Tetra Laval Holdings & Finance S.A. Laminated color forming composition
EP3950068A4 (en) * 2019-03-29 2022-12-14 The Pilot Ink Co., Ltd. Reversible thermochromic composition, reversible thermochromic microcapsule pigment comprising same, and writing instrument using same

Also Published As

Publication number Publication date
FR2400053A1 (en) 1979-03-09
FR2400053B1 (en) 1981-09-11
FI69859C (en) 1986-05-26
GB2002801B (en) 1982-02-17
FI69859B (en) 1985-12-31
DE2834711A1 (en) 1979-02-15
DE2834711C2 (en) 1985-02-21
FI782420A (en) 1979-02-09
JPS5434909A (en) 1979-03-14
JPS5652759B2 (en) 1981-12-14

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Legal Events

Date Code Title Description
711A Proceeding under section 117(1) patents act 1977
PE20 Patent expired after termination of 20 years

Effective date: 19980807