US3920510A - Pressure-and-heat-sensitive copying paper - Google Patents

Pressure-and-heat-sensitive copying paper Download PDF

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Publication number
US3920510A
US3920510A US384304A US38430473A US3920510A US 3920510 A US3920510 A US 3920510A US 384304 A US384304 A US 384304A US 38430473 A US38430473 A US 38430473A US 3920510 A US3920510 A US 3920510A
Authority
US
United States
Prior art keywords
heat
copying paper
sensitive copying
methyl
diethylaminofluoran
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.)
Expired - Lifetime
Application number
US384304A
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English (en)
Inventor
Yoshihiro Hatano
Kenji Yamamoto
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.)
Yamamoto Chemicals Inc
Original Assignee
Yamamoto Chemicals Inc
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 Yamamoto Chemicals Inc filed Critical Yamamoto Chemicals Inc
Application granted granted Critical
Publication of US3920510A publication Critical patent/US3920510A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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

Definitions

  • ABSTRACT A heat or pressure sensitive copying paper is provided containing a fluoran compound as a color former, said color being developed in said heat or pressure sensitive copying paper through the application of heat or pressure, said fluoran compound being of the formula (III) wherein R is halogen; R is hydrogen or methyl; R is hydrogen, methyl or ethyl; each of R is independently halogen or methyl; R is methyl or ethyl; and n is O or an integer from 1 to 4.
  • the present invention relates to copying paper which is heat or pressure sensitive which contains aggregater former.
  • a new series of fluoran compounds are provided which serve as a color former for this paper.
  • the fluoran compounds of the invention are particu larly useful for developing color in the copying paper having a green or black shade.
  • the fluoran compounds have the general formula wherein R is halogen; R is hydrogen or methyl; R is hydrogen, methyl or ethyl; each of R is independently halogen or methyl; R or ethyl; and n is 0 or an integer from 1 to 4.
  • Such fluroan compounds as ([11) may be applied to the pressure-sensitive copying'paper in a manner, for example, described in the Japanese Pat. No. 4,614/1971.
  • a dye for the pressure-sensitive copying paper is generally applicable to the heat-sensitive copying paper in such a manner as is described in the Japanese Pat. No. 14,039/1970.
  • the product ([1]) can also be applied to the heat-sensitive copying paper in a similar manner.
  • the dye is used for the heat-sensitive copying paper, it is not used in microcapsules of gelatin etc., as in the case of the pressure-sensitive copying paper.
  • 2-anilino-6-diethylaminofluoran compound IV, developing into a green color
  • 2-anilino-3-methyl-6-diethylaminofluoran compound V, developing into a black color
  • Belgian Pat. No. 744,705 is known as the dyes for pressure-sensitive copying paper that singly develop into a green or black color:
  • fluroan compounds not only are very useful as the dye for heat-sensitive copying paper but also have a high practical value as the dye for pressure-sensitive copying paper.
  • EXAMPLE 14 EXAMPLE 15 Preparation of Preparation of 2-(4'-chloro-N-methylanilino)-6-diethylaminofluoran 2-(4'-chloro-N-ethylanilino)-6-diethylaminofluoran (XXXllI) (XXXV) 2 s 0 0 c H c n /N 1 l m c Ii /N' l 5 2 5 N-U-CZ 2 5 l N o o C O C '-'-"O C11.
  • EXAMPLE 17 Preparation of pressure sensitive copying paper 5 g of 2-p-chloroanilino-6-diethylaminofluoran (VI, Example 1 is heated with g of mono-isopropyl biphenyl up to 100C and dissolved into the latter, and then emulsified together with a solution of 25 g of gum arabic in 400 ml of water. Next, a solution of 25 g of gelatin in 400 ml of water is added to complete the emulsification, and acetic acid is added to adjust so as to obtain pH 4. At this time, liquid films of gelatin/gum arabic are formed around oil drops containing fluoran compound.
  • EXAMPLE 18 Preparation of heat-sensitive copying paper 35 G of 2-p-chloroanilino-3-methyl-6-diethylamino fluoran (XVII, Example 6), g of 10 weight percent polyvinyl alcoholaqueous solution, and 65 g of water are ground and mixed for an hour. (A liquid).
  • a heat or pressure sensitive copying paper of claim 1 wherein said fluoran is 2-m-chloroanilino-6-diethylaminot'luoran.
  • a heat or pressure sensitive copying paper of claim 1 wherein said fluoran is 2-( 3',5'-dichloroanilino)-6- diethylaminofluoran.
  • a heat or pressure sensitive copying paper of claim 1 wherein said fluoran is 2-(3',4'-dichloroanilino)-6- diethylaminofluoran.
  • a heat or pressure sensitive copying paper of claim 1 wherein said fluoran is 2-p-chloroanilino-3-methyl-6- diethylaminofluoran.
  • a heat or pressure sensitive copying paper of claim 1 wherein said fluoran is 2-m-chloroanilino-3-methyl- 6-diethylaminofluoran.
  • a heat or pressure sensitive copying paper of claim 1 wherein said fluoran is 2-o-chloroanilino-3-methyl-6- diethylaminofluoran.
  • fluoran is 2-(4'-chloro-N- methylanilino)-6-diethylaminofluoran.

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)
US384304A 1972-08-01 1973-07-31 Pressure-and-heat-sensitive copying paper Expired - Lifetime US3920510A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP47077081A JPS4934526A (enrdf_load_stackoverflow) 1972-08-01 1972-08-01

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US06/153,660 Reissue USRE31412E (en) 1972-08-01 1980-05-27 Pressure-and-heat-sensitive copying paper

Publications (1)

Publication Number Publication Date
US3920510A true US3920510A (en) 1975-11-18

Family

ID=13623817

Family Applications (2)

Application Number Title Priority Date Filing Date
US384304A Expired - Lifetime US3920510A (en) 1972-08-01 1973-07-31 Pressure-and-heat-sensitive copying paper
US06/153,660 Expired - Lifetime USRE31412E (en) 1972-08-01 1980-05-27 Pressure-and-heat-sensitive copying paper

Family Applications After (1)

Application Number Title Priority Date Filing Date
US06/153,660 Expired - Lifetime USRE31412E (en) 1972-08-01 1980-05-27 Pressure-and-heat-sensitive copying paper

Country Status (2)

Country Link
US (2) US3920510A (enrdf_load_stackoverflow)
JP (1) JPS4934526A (enrdf_load_stackoverflow)

Cited By (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4156682A (en) * 1973-10-05 1979-05-29 Sumitomo Chemical Company, Limited Fluoran compounds and recording sheet containing them
FR2417396A1 (fr) * 1978-02-15 1979-09-14 Kanzaki Paper Mfg Co Ltd Support d'enregistrement thermosensible
US4287264A (en) * 1980-03-07 1981-09-01 Labelon Corporation Heat sensitive coating
EP0048026A1 (en) * 1980-09-17 1982-03-24 Hodogaya Chemical Co., Ltd. Heat sensitive record sheet
EP0098151A3 (en) * 1982-06-29 1984-03-21 Mita Industrial Co. Ltd. Heat-sensitive black recording element
EP0098728A3 (en) * 1982-06-30 1984-03-21 Mita Industrial Co. Ltd. Heat-sensitive black recording material
US4510513A (en) * 1983-04-14 1985-04-09 Hodogaya Chemical Co., Ltd. Heat sensitive record sheet
US4515971A (en) * 1980-03-31 1985-05-07 Hilton-Davis Chemical Co. 5'/6'-Carboxyfluorans and derivatives thereof
US4524373A (en) * 1982-02-24 1985-06-18 Kanzaki Paper Manufacturing Co., Ltd. Fluoran derivatives as new compounds, process for preparing the same and recording system utilizing the same as colorless chromogenic material
US4927802A (en) * 1988-12-09 1990-05-22 Ppg Industries, Inc. Pressure-sensitive multi-part record unit
US5166350A (en) * 1989-06-10 1992-11-24 Ciba-Geigy Corporation Process for the manufacture of fluoran compounds
US5284816A (en) * 1992-11-19 1994-02-08 Eastman Kodak Company Two-sided thermal printing system
EP0688759A1 (en) 1994-06-23 1995-12-27 Fuji Photo Film Co., Ltd. Alpha-resorcylic acid ester derivatives and recording materials incorporating them
US6037094A (en) * 1998-10-23 2000-03-14 Cycolor, Inc. Photosensitive material employing microcapsules and superabsorbent polymer
US6127084A (en) * 1998-10-23 2000-10-03 Cycolor, Inc. Photosensitive material employing microcapsules containing a hygroscopic polymer in the internal phase
US6638678B2 (en) 2001-11-20 2003-10-28 Hsbc Bank Usa Method for improving sensitometric response of photosensitive imaging media employing microcapsules
US20040169071A1 (en) * 2003-02-28 2004-09-02 Appleton Papers Inc. Token array and method employing authentication tokens bearing scent formulation information
US20040214134A1 (en) * 2003-04-22 2004-10-28 Appleton Papers Inc. Dental articulation kit and method
US20040251309A1 (en) * 2003-06-10 2004-12-16 Appleton Papers Inc. Token bearing magnetc image information in registration with visible image information
US6964836B2 (en) 2002-03-15 2005-11-15 Eastman Kodak Company Photosensitive microcapsules containing a synthetic viscosity modifier in the continuous phase
US20060063125A1 (en) * 2003-04-22 2006-03-23 Hamilton Timothy F Method and device for enhanced dental articulation
US20080248950A1 (en) * 2007-04-04 2008-10-09 Ibrahim Katampe Ink and Developer System
WO2009121247A1 (en) * 2008-04-05 2009-10-08 Versitech Limited Luminescence quenchers and fluorogenic probes for detection of reactive species
WO2010090213A1 (ja) 2009-02-04 2010-08-12 富士フイルム株式会社 熱分布表示体及び熱分布確認方法
JP2013001838A (ja) * 2011-06-17 2013-01-07 Japan Aerospace Exploration Agency ポリマー連結型複合分子塗料とそれを用いたセンサ
WO2014124052A1 (en) 2013-02-06 2014-08-14 Fujifilm Hunt Chemicals, Inc. Chemical coating for a laser-markable material
WO2015094630A1 (en) 2013-12-18 2015-06-25 Appvion, Inc. Thermal recording materials
US9409219B2 (en) 2011-02-07 2016-08-09 Valspar Sourcing, Inc. Compositions for containers and other articles and methods of using same
US9475328B2 (en) 2012-08-09 2016-10-25 Valspar Sourcing, Inc. Developer for thermally responsive record materials
US9724276B2 (en) 2012-08-09 2017-08-08 Valspar Sourcing, Inc. Dental materials and method of manufacture
US9944749B2 (en) 2012-08-09 2018-04-17 Swimc, Llc Polycarbonates
US10113027B2 (en) 2014-04-14 2018-10-30 Swimc Llc Methods of preparing compositions for containers and other articles and methods of using same
US10316211B2 (en) 2012-08-09 2019-06-11 Swimc Llc Stabilizer and coating compositions thereof
US10435199B2 (en) 2012-08-09 2019-10-08 Swimc Llc Compositions for containers and other articles and methods of using same
US10526502B2 (en) 2012-08-09 2020-01-07 Swimc Llc Container coating system
US11130835B2 (en) 2015-11-03 2021-09-28 Swimc Llc Liquid epoxy resin composition useful for making polymers
US11130881B2 (en) 2010-04-16 2021-09-28 Swimc Llc Coating compositions for packaging articles and methods of coating

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS58162663A (ja) * 1982-03-19 1983-09-27 Fuji Photo Film Co Ltd フルオラン誘導体およびそれを使用した記録材料
JPS59136349A (ja) * 1983-01-25 1984-08-04 Yamada Kagaku Kogyo Kk フルオラン化合物及びそれを使用した発色性記録材料

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3669712A (en) * 1969-06-27 1972-06-13 Fuji Photo Film Co Ltd Pressure-sensitive copying papers
US3681390A (en) * 1970-11-16 1972-08-01 Ncr Co Dialkylamino fluoran chromogenic compounds
US3746562A (en) * 1970-11-16 1973-07-17 Ncr Mark forming record materials
US3764369A (en) * 1969-01-21 1973-10-09 Ncr Pressure sensitive recording unit

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2065117A5 (enrdf_load_stackoverflow) 1969-10-08 1971-07-23 Fuji Photo Film Co Ltd
US3825561A (en) 1970-10-12 1974-07-23 Sumitomo Chemical Co Fluoran compounds

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3764369A (en) * 1969-01-21 1973-10-09 Ncr Pressure sensitive recording unit
US3669712A (en) * 1969-06-27 1972-06-13 Fuji Photo Film Co Ltd Pressure-sensitive copying papers
US3681390A (en) * 1970-11-16 1972-08-01 Ncr Co Dialkylamino fluoran chromogenic compounds
US3746562A (en) * 1970-11-16 1973-07-17 Ncr Mark forming record materials

Cited By (54)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4156682A (en) * 1973-10-05 1979-05-29 Sumitomo Chemical Company, Limited Fluoran compounds and recording sheet containing them
FR2417396A1 (fr) * 1978-02-15 1979-09-14 Kanzaki Paper Mfg Co Ltd Support d'enregistrement thermosensible
US4287264A (en) * 1980-03-07 1981-09-01 Labelon Corporation Heat sensitive coating
US4515971A (en) * 1980-03-31 1985-05-07 Hilton-Davis Chemical Co. 5'/6'-Carboxyfluorans and derivatives thereof
EP0048026A1 (en) * 1980-09-17 1982-03-24 Hodogaya Chemical Co., Ltd. Heat sensitive record sheet
US4364999A (en) * 1980-09-17 1982-12-21 Hodogaya Chemical Co., Ltd. Heat sensitive record sheet
US4524373A (en) * 1982-02-24 1985-06-18 Kanzaki Paper Manufacturing Co., Ltd. Fluoran derivatives as new compounds, process for preparing the same and recording system utilizing the same as colorless chromogenic material
EP0098151A3 (en) * 1982-06-29 1984-03-21 Mita Industrial Co. Ltd. Heat-sensitive black recording element
EP0098728A3 (en) * 1982-06-30 1984-03-21 Mita Industrial Co. Ltd. Heat-sensitive black recording material
US4510513A (en) * 1983-04-14 1985-04-09 Hodogaya Chemical Co., Ltd. Heat sensitive record sheet
USRE33815E (en) * 1983-04-14 1992-02-04 Hodogaya Chemical Co., Ltd. Heat sensitive record sheet
US4927802A (en) * 1988-12-09 1990-05-22 Ppg Industries, Inc. Pressure-sensitive multi-part record unit
US5166350A (en) * 1989-06-10 1992-11-24 Ciba-Geigy Corporation Process for the manufacture of fluoran compounds
US5284816A (en) * 1992-11-19 1994-02-08 Eastman Kodak Company Two-sided thermal printing system
EP0688759A1 (en) 1994-06-23 1995-12-27 Fuji Photo Film Co., Ltd. Alpha-resorcylic acid ester derivatives and recording materials incorporating them
US6037094A (en) * 1998-10-23 2000-03-14 Cycolor, Inc. Photosensitive material employing microcapsules and superabsorbent polymer
US6127084A (en) * 1998-10-23 2000-10-03 Cycolor, Inc. Photosensitive material employing microcapsules containing a hygroscopic polymer in the internal phase
US6638678B2 (en) 2001-11-20 2003-10-28 Hsbc Bank Usa Method for improving sensitometric response of photosensitive imaging media employing microcapsules
US6964836B2 (en) 2002-03-15 2005-11-15 Eastman Kodak Company Photosensitive microcapsules containing a synthetic viscosity modifier in the continuous phase
US20040169071A1 (en) * 2003-02-28 2004-09-02 Appleton Papers Inc. Token array and method employing authentication tokens bearing scent formulation information
US7108190B2 (en) 2003-02-28 2006-09-19 Appleton Papers Inc. Token array and method employing authentication tokens bearing scent formulation information
US20040214134A1 (en) * 2003-04-22 2004-10-28 Appleton Papers Inc. Dental articulation kit and method
US6932602B2 (en) 2003-04-22 2005-08-23 Appleton Papers Inc. Dental articulation kit and method
US20060063125A1 (en) * 2003-04-22 2006-03-23 Hamilton Timothy F Method and device for enhanced dental articulation
US20040251309A1 (en) * 2003-06-10 2004-12-16 Appleton Papers Inc. Token bearing magnetc image information in registration with visible image information
US20080248950A1 (en) * 2007-04-04 2008-10-09 Ibrahim Katampe Ink and Developer System
WO2009121247A1 (en) * 2008-04-05 2009-10-08 Versitech Limited Luminescence quenchers and fluorogenic probes for detection of reactive species
US8114904B2 (en) 2008-04-05 2012-02-14 Versitech Limited & Morningside Ventures Limited Luminescence quenchers and fluorogenic probes for detection of reactive species
US20090253118A1 (en) * 2008-04-05 2009-10-08 Versitech Limited Luminescence quenchers and fluorogenic probes for detection of reactive species
WO2010090213A1 (ja) 2009-02-04 2010-08-12 富士フイルム株式会社 熱分布表示体及び熱分布確認方法
US12234371B2 (en) 2010-04-16 2025-02-25 Swimc Llc Coating compositions for packaging articles and methods of coating
US11130881B2 (en) 2010-04-16 2021-09-28 Swimc Llc Coating compositions for packaging articles and methods of coating
US10294388B2 (en) 2011-02-07 2019-05-21 Swimc Llc Compositions for containers and other articles and methods of using same
US11634607B2 (en) 2011-02-07 2023-04-25 Swimc Llc Compositions for containers and other articles and methods of using same
US9409219B2 (en) 2011-02-07 2016-08-09 Valspar Sourcing, Inc. Compositions for containers and other articles and methods of using same
US11053409B2 (en) 2011-02-07 2021-07-06 Jeffrey Niederst Compositions for containers and other articles and methods of using same
JP2013001838A (ja) * 2011-06-17 2013-01-07 Japan Aerospace Exploration Agency ポリマー連結型複合分子塗料とそれを用いたセンサ
US10316211B2 (en) 2012-08-09 2019-06-11 Swimc Llc Stabilizer and coating compositions thereof
US11628974B2 (en) 2012-08-09 2023-04-18 Swimc Llc Compositions for containers and other articles and methods of using same
US9944749B2 (en) 2012-08-09 2018-04-17 Swimc, Llc Polycarbonates
US10435199B2 (en) 2012-08-09 2019-10-08 Swimc Llc Compositions for containers and other articles and methods of using same
US10526502B2 (en) 2012-08-09 2020-01-07 Swimc Llc Container coating system
US10894632B2 (en) 2012-08-09 2021-01-19 Swimc Llc Compositions for containers and other articles and methods of using same
US9724276B2 (en) 2012-08-09 2017-08-08 Valspar Sourcing, Inc. Dental materials and method of manufacture
US12043448B2 (en) 2012-08-09 2024-07-23 Swimc Llc Compositions for containers and other articles and methods of using same
US9475328B2 (en) 2012-08-09 2016-10-25 Valspar Sourcing, Inc. Developer for thermally responsive record materials
US11306218B2 (en) 2012-08-09 2022-04-19 Swimc Llc Container coating system
WO2014124052A1 (en) 2013-02-06 2014-08-14 Fujifilm Hunt Chemicals, Inc. Chemical coating for a laser-markable material
WO2015094630A1 (en) 2013-12-18 2015-06-25 Appvion, Inc. Thermal recording materials
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Also Published As

Publication number Publication date
USRE31412E (en) 1983-10-11
JPS4934526A (enrdf_load_stackoverflow) 1974-03-30

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