US3617335A - Pressure-sensitive copying paper - Google Patents

Pressure-sensitive copying paper Download PDF

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Publication number
US3617335A
US3617335A US842008A US3617335DA US3617335A US 3617335 A US3617335 A US 3617335A US 842008 A US842008 A US 842008A US 3617335D A US3617335D A US 3617335DA US 3617335 A US3617335 A US 3617335A
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US
United States
Prior art keywords
group
pressure
color
paper
acid
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
US842008A
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English (en)
Inventor
Shiro Kimura
Teruo Kobayashi
Sadao Ishige
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.)
Fujifilm Holdings Corp
Original Assignee
Fuji Photo Film 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 Fuji Photo Film Co Ltd filed Critical Fuji Photo Film Co Ltd
Application granted granted Critical
Publication of US3617335A publication Critical patent/US3617335A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C09B11/26—Triarylmethane dyes in which at least one of the aromatic nuclei is heterocyclic
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/025—Applications of microcapsules not provided for in other subclasses
    • 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
    • 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

Definitions

  • a pressure-sensitive copying paper comprising a support having coated thereon microcapsules containing an organic solvent solution of a compound which, when in contact with an electron acceptable solid acid, forms a color dye and is represented by the following formula:
  • alkyl group having from one to 17 carbon atoms, an aryl group, an amino group, an acylamino group and an alkoxy group having from one to five carbon atoms.
  • This invention relates to a pressure-sensitive copying paper and in particular, it is concerned with a pressure-sensitive copying paper using as a color former a compound represented by the following general formula:
  • R and R are alkyl groups of one to five carbon atoms or benzyl groups
  • X is an alkyl group of one to five carbon atoms or an aryl group
  • Y is an alkyl group of one to 17 carbon atoms, an aryl group, an amino group, an acylamino group or an alkoxy group.
  • Ordinary pressure-sensitive copying paper consists of an upper paper onto which is coated a substantially colorless organic compound having an electron-donating property and a color forming reactivity (hereinafter referred to as a color former") dissolved in an organic solvent and incorporated in microcapsules and a lower paper, onto which is coated electron-acceptable solid acid. If necessary, an intermediate paper layer is provided onto one side thereof is coated the colorformer-containing microcapsules and on the other side thereof is coated a solid acid, and a support on one side of which the microcapsules and solid acid are coated.
  • a color former color forming reactivity
  • the papers are pressed locally in such a manner that the microcapsules-containing layer and the solid acid-containing layer are contacted, whereby the microcapsules in this pressurized area are broken and the color former is reacted with the solid acid, thus color forming.
  • the paper may be pressed for color forming by means of a typewriter, for example.
  • color formers coloring in red and blue are the following: leuco triphenylmethane derivatives, leuco methylene blue acyl derivatives, and triphenylmethane and xanthene phthalide derivatives having lactone rings.
  • color formers coloring in yellow orange to orange red there are not many color formers coloring in yellow orange to orange red.
  • These color formers have the following disadvantages. That is to say, o-hydroxybenzalacetophenone has a low color forming density. 2-(4-hydroxystyryl)-3,3-dimethyl- 3I-l-indole or 2-(4-acetamidestry1)-3,3-dimethyl-3H-indole (cf. Japan Pat. publication No.
  • 21033/1966 has a high color forming density and relatively strong light resistance after color forming, but the light resistance before color forming and water resistance after color forming are weak. If a color former coloring in yellow-orange to orange-red is obtained which has a higher color density, higher color forming speed and stronger light resistance and water resistance before and after color forming than those known in the art, a pressuresensitive copying paper coloring in yellow-orange to orangered as well as a pressure-sensitive copying paper coloring in an optional color such as black or blue-black used together with a known color former coloring in red or blue will be given. This advantage enlarges the application of pressure-sensitive copying papers.
  • a pressure-sensitive copying paper according to the present invention using the compound of the foregoing general formula has an excellent stability in air before color forming, is free from coloring and lowering of the color forming ability, colored in yelloworange to orange-red immediately when contacted with an electron-accepting solid, acid, thus resulting in a high color density and is strongly resistant to light and water after color forming,
  • a known color former coloring in red or blue it colors in various colors such as black and blue-black without being desensitized.
  • the pressure-sensitive copying paper of the present invention For the production of the pressure-sensitive copying paper of the present invention using the compound represented by the general formula, a method of making microcapsules by utilizing the complexed coacervation is employed, for example, which is disclosed in US. Pat. Nos. 2,548,366, 2,800,457 and 2,800,458 as being well-known to those skilled in the art.
  • the instant invention is characterized by the use of the compound represented by the foregoing general formula as a color former.
  • the characteristics of the pressure-sensitive copying paper are independent from the production method thereof.
  • the amount of the color former used is generally 0.5-5 percent by weight based on the organic solvent.
  • EXAMPLE 1 Three grams of each of the color formers (I)-(Il) was The color former was dissolved in g. of trichlorodiphenyl. To the resulting solution were added 20 g. of gum arabic and g. of water at 50 C. to given an emulsion, further, 20 g. of acid-treated gelatin and 160 g. of water and then acetic acid were added, while stirring to adjust the pH to 5. Then, 500 g. of water was added thereto to advance the coacervation to form a thickened liquid film of gelatin-gum arabic around the oil drop of trichlorodiphenyl dissolving the color former. After adjusting the pH to 4.4, 3.8 g.
  • the thus capsulized liquid was coated onto a sheet of paper by roll coating or by air knife coating and then dried.
  • the coated paper upper paper
  • another sheet of paper lower paper
  • an electron-accepting solid acid such as acid clay. active clay, attapulgite, zeolite or bentonite and pressed by means of a pencil or typewriter, there instantaneously occurred a thick color formation on the pressed area of the lower sheet of paper.
  • a yellow-orange color was noted in the color formers (l), (2), (4,), (5), (6) and (10) orange in (3). (7). and (11); and orange-red in (8) and (9).
  • These color formed dyes were scarcely faded even though exposed to direct sunlight for a long time or wetted with water.
  • EXAMPLE 2 l The pressure-sensitive copying paper as claimed in claim The procedure of example 1 was repeated, except that 1.51 l saldh electromacgpiable i a memtier g. of the color former (2) was used with the known color for- Se ecte mm t B group conslstmg 0 an acid c an acme mers, i.e., 0.3 g. of Benzoyl Leuco Methylene blue, 0.5 g. of i g l Succlmc acid tanmc l hite Green Lactone 0 7 of Cr stal Violet Lactone lc an Pema? Drop Ma ac 8- y t 5 4.
  • a pressure-sensitive copying paper comprising a support 8 'P "Y auramme and 8- of Rhodamme B having coated thereon an electron-acceptable solid acid and Anilinolactam.
  • EXAMPLE 3 R The procedure of example 1 was repeated, except that 0.3 N- f g. of the color former (4) and 0.7 g. of the color forrner (8) were used with 0.5 g. of Benzoyl Leuco Methylene Blue, 2.0 g.
  • a pressure-sensitive copying paper comprising and under paper having coated thereon an electron-acceptable solid acid and an upper paper having coated thereon microcapsules containing an organic solvent solution of a compound which is in contact with said electron-acceptable solid acid to form a color dye and is represented by the following formula:
  • a pressure-sensitive copying paper comprising a support X having coated thereon microcapsules containing an organic i; ⁇ solvent solution of a compound which, when in contact with N N an electron acceptable solid acid, forms a color dye and is i represented by the following formula: C Y
  • R and R each represents a member selected from I the group consisting of an alkyl group having from one to five carbon atoms and a benzyl group
  • X represents a member selected from the group consisting of an alkyl group having from one to five carbon atoms and an aryl group
  • Y wherein R and R each represents a member selected from represents a member selected from the group consisting of an the group consisting of an alkyl group having from one to five alkyl group having from one to 17 carbon atoms, an aryl carbon atoms and a benzyl group
  • X represents a member group, an amino group, an acylamino group and an alkoxy selected from the group consisting of an alkyl group having group having from one to five carbon atoms.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Color Printing (AREA)
US842008A 1968-07-15 1969-07-15 Pressure-sensitive copying paper Expired - Lifetime US3617335A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP4981768 1968-07-15

Publications (1)

Publication Number Publication Date
US3617335A true US3617335A (en) 1971-11-02

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ID=12841656

Family Applications (1)

Application Number Title Priority Date Filing Date
US842008A Expired - Lifetime US3617335A (en) 1968-07-15 1969-07-15 Pressure-sensitive copying paper

Country Status (4)

Country Link
US (1) US3617335A (enrdf_load_stackoverflow)
ES (1) ES369481A1 (enrdf_load_stackoverflow)
GB (1) GB1264636A (enrdf_load_stackoverflow)
IE (1) IE33222B1 (enrdf_load_stackoverflow)

Cited By (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3974175A (en) * 1973-09-06 1976-08-10 Ciba-Geigy Ag Nitro-chromeno pyrazole compounds their manufacture and use
US3983292A (en) * 1971-08-27 1976-09-28 Sanko Chemical Company Ltd. Pressure sensitive recording papers
US5681380A (en) 1995-06-05 1997-10-28 Kimberly-Clark Worldwide, Inc. Ink for ink jet printers
US5709955A (en) 1994-06-30 1998-01-20 Kimberly-Clark Corporation Adhesive composition curable upon exposure to radiation and applications therefor
US5721287A (en) 1993-08-05 1998-02-24 Kimberly-Clark Worldwide, Inc. Method of mutating a colorant by irradiation
US5733693A (en) 1993-08-05 1998-03-31 Kimberly-Clark Worldwide, Inc. Method for improving the readability of data processing forms
US5773182A (en) 1993-08-05 1998-06-30 Kimberly-Clark Worldwide, Inc. Method of light stabilizing a colorant
US5782963A (en) 1996-03-29 1998-07-21 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5786132A (en) 1995-06-05 1998-07-28 Kimberly-Clark Corporation Pre-dyes, mutable dye compositions, and methods of developing a color
US5837429A (en) 1995-06-05 1998-11-17 Kimberly-Clark Worldwide Pre-dyes, pre-dye compositions, and methods of developing a color
US5855655A (en) 1996-03-29 1999-01-05 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5858586A (en) 1993-08-05 1999-01-12 Kimberly-Clark Corporation Digital information recording media and method of using same
US5865471A (en) 1993-08-05 1999-02-02 Kimberly-Clark Worldwide, Inc. Photo-erasable data processing forms
US5885337A (en) 1995-11-28 1999-03-23 Nohr; Ronald Sinclair Colorant stabilizers
US5891229A (en) 1996-03-29 1999-04-06 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US6008268A (en) 1994-10-21 1999-12-28 Kimberly-Clark Worldwide, Inc. Photoreactor composition, method of generating a reactive species, and applications therefor
US6017471A (en) 1993-08-05 2000-01-25 Kimberly-Clark Worldwide, Inc. Colorants and colorant modifiers
US6017661A (en) 1994-11-09 2000-01-25 Kimberly-Clark Corporation Temporary marking using photoerasable colorants
US6033465A (en) 1995-06-28 2000-03-07 Kimberly-Clark Worldwide, Inc. Colorants and colorant modifiers
US6071979A (en) 1994-06-30 2000-06-06 Kimberly-Clark Worldwide, Inc. Photoreactor composition method of generating a reactive species and applications therefor
US6099628A (en) 1996-03-29 2000-08-08 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US6211383B1 (en) 1993-08-05 2001-04-03 Kimberly-Clark Worldwide, Inc. Nohr-McDonald elimination reaction
US6228157B1 (en) 1998-07-20 2001-05-08 Ronald S. Nohr Ink jet ink compositions
US6242057B1 (en) 1994-06-30 2001-06-05 Kimberly-Clark Worldwide, Inc. Photoreactor composition and applications therefor
US6265458B1 (en) 1998-09-28 2001-07-24 Kimberly-Clark Worldwide, Inc. Photoinitiators and applications therefor
US6277897B1 (en) 1998-06-03 2001-08-21 Kimberly-Clark Worldwide, Inc. Photoinitiators and applications therefor
US6294698B1 (en) 1999-04-16 2001-09-25 Kimberly-Clark Worldwide, Inc. Photoinitiators and applications therefor
US6331056B1 (en) 1999-02-25 2001-12-18 Kimberly-Clark Worldwide, Inc. Printing apparatus and applications therefor
US6368396B1 (en) 1999-01-19 2002-04-09 Kimberly-Clark Worldwide, Inc. Colorants, colorant stabilizers, ink compositions, and improved methods of making the same
US6368395B1 (en) 1999-05-24 2002-04-09 Kimberly-Clark Worldwide, Inc. Subphthalocyanine colorants, ink compositions, and method of making the same
US6503559B1 (en) 1998-06-03 2003-01-07 Kimberly-Clark Worldwide, Inc. Neonanoplasts and microemulsion technology for inks and ink jet printing
US6524379B2 (en) 1997-08-15 2003-02-25 Kimberly-Clark Worldwide, Inc. Colorants, colorant stabilizers, ink compositions, and improved methods of making the same
CN102329524A (zh) * 2011-06-28 2012-01-25 淮阴工学院 一种基于凹凸棒石固载的高耐候性复合颜料的制备方法
US9399716B2 (en) 2013-07-02 2016-07-26 Chromatic Technologies Inc. Yellow thermochromic dyes, inks composition and level indicators
US9580603B2 (en) 2013-09-27 2017-02-28 Chromatic Technologies, Inc. Red thermochromic dyes and their ink compositions

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2064481T3 (es) * 1988-04-27 1995-02-01 Ciba Geigy Ag Compuestos lactona cromogenos de benzopirano-2h-pirazoles.

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3491116A (en) * 1967-01-30 1970-01-20 Ncr Co 3-(phenyl)-3-(indol-3-yl)-phthalides
US3499902A (en) * 1967-08-09 1970-03-10 Minnesota Mining & Mfg Organic hydrazone compound containing azo coupler moiety
US3509174A (en) * 1967-01-30 1970-04-28 Ncr Co 3-(indol-3-yl)-phthalides

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3491116A (en) * 1967-01-30 1970-01-20 Ncr Co 3-(phenyl)-3-(indol-3-yl)-phthalides
US3509174A (en) * 1967-01-30 1970-04-28 Ncr Co 3-(indol-3-yl)-phthalides
US3499902A (en) * 1967-08-09 1970-03-10 Minnesota Mining & Mfg Organic hydrazone compound containing azo coupler moiety

Cited By (50)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3983292A (en) * 1971-08-27 1976-09-28 Sanko Chemical Company Ltd. Pressure sensitive recording papers
US3974175A (en) * 1973-09-06 1976-08-10 Ciba-Geigy Ag Nitro-chromeno pyrazole compounds their manufacture and use
US6120949A (en) 1993-08-05 2000-09-19 Kimberly-Clark Worldwide, Inc. Photoerasable paint and method for using photoerasable paint
US5865471A (en) 1993-08-05 1999-02-02 Kimberly-Clark Worldwide, Inc. Photo-erasable data processing forms
US5721287A (en) 1993-08-05 1998-02-24 Kimberly-Clark Worldwide, Inc. Method of mutating a colorant by irradiation
US5733693A (en) 1993-08-05 1998-03-31 Kimberly-Clark Worldwide, Inc. Method for improving the readability of data processing forms
US5773182A (en) 1993-08-05 1998-06-30 Kimberly-Clark Worldwide, Inc. Method of light stabilizing a colorant
US6127073A (en) 1993-08-05 2000-10-03 Kimberly-Clark Worldwide, Inc. Method for concealing information and document for securely communicating concealed information
US6017471A (en) 1993-08-05 2000-01-25 Kimberly-Clark Worldwide, Inc. Colorants and colorant modifiers
US6054256A (en) 1993-08-05 2000-04-25 Kimberly-Clark Worldwide, Inc. Method and apparatus for indicating ultraviolet light exposure
US6066439A (en) 1993-08-05 2000-05-23 Kimberly-Clark Worldwide, Inc. Instrument for photoerasable marking
US5858586A (en) 1993-08-05 1999-01-12 Kimberly-Clark Corporation Digital information recording media and method of using same
US6211383B1 (en) 1993-08-05 2001-04-03 Kimberly-Clark Worldwide, Inc. Nohr-McDonald elimination reaction
US6060223A (en) 1993-08-05 2000-05-09 Kimberly-Clark Worldwide, Inc. Plastic article for colored printing and method for printing on a colored plastic article
US6060200A (en) 1993-08-05 2000-05-09 Kimberly-Clark Worldwide, Inc. Photo-erasable data processing forms and methods
US5908495A (en) 1993-08-05 1999-06-01 Nohr; Ronald Sinclair Ink for ink jet printers
US6342305B1 (en) 1993-09-10 2002-01-29 Kimberly-Clark Corporation Colorants and colorant modifiers
US6071979A (en) 1994-06-30 2000-06-06 Kimberly-Clark Worldwide, Inc. Photoreactor composition method of generating a reactive species and applications therefor
US6090236A (en) 1994-06-30 2000-07-18 Kimberly-Clark Worldwide, Inc. Photocuring, articles made by photocuring, and compositions for use in photocuring
US6242057B1 (en) 1994-06-30 2001-06-05 Kimberly-Clark Worldwide, Inc. Photoreactor composition and applications therefor
US5709955A (en) 1994-06-30 1998-01-20 Kimberly-Clark Corporation Adhesive composition curable upon exposure to radiation and applications therefor
US6008268A (en) 1994-10-21 1999-12-28 Kimberly-Clark Worldwide, Inc. Photoreactor composition, method of generating a reactive species, and applications therefor
US6017661A (en) 1994-11-09 2000-01-25 Kimberly-Clark Corporation Temporary marking using photoerasable colorants
US6235095B1 (en) 1994-12-20 2001-05-22 Ronald Sinclair Nohr Ink for inkjet printers
US5681380A (en) 1995-06-05 1997-10-28 Kimberly-Clark Worldwide, Inc. Ink for ink jet printers
US5837429A (en) 1995-06-05 1998-11-17 Kimberly-Clark Worldwide Pre-dyes, pre-dye compositions, and methods of developing a color
US6063551A (en) 1995-06-05 2000-05-16 Kimberly-Clark Worldwide, Inc. Mutable dye composition and method of developing a color
US5786132A (en) 1995-06-05 1998-07-28 Kimberly-Clark Corporation Pre-dyes, mutable dye compositions, and methods of developing a color
US6033465A (en) 1995-06-28 2000-03-07 Kimberly-Clark Worldwide, Inc. Colorants and colorant modifiers
US5885337A (en) 1995-11-28 1999-03-23 Nohr; Ronald Sinclair Colorant stabilizers
US6168655B1 (en) 1995-11-28 2001-01-02 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US6168654B1 (en) 1996-03-29 2001-01-02 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5782963A (en) 1996-03-29 1998-07-21 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5891229A (en) 1996-03-29 1999-04-06 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US6099628A (en) 1996-03-29 2000-08-08 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5855655A (en) 1996-03-29 1999-01-05 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US6524379B2 (en) 1997-08-15 2003-02-25 Kimberly-Clark Worldwide, Inc. Colorants, colorant stabilizers, ink compositions, and improved methods of making the same
US6277897B1 (en) 1998-06-03 2001-08-21 Kimberly-Clark Worldwide, Inc. Photoinitiators and applications therefor
US6503559B1 (en) 1998-06-03 2003-01-07 Kimberly-Clark Worldwide, Inc. Neonanoplasts and microemulsion technology for inks and ink jet printing
US6228157B1 (en) 1998-07-20 2001-05-08 Ronald S. Nohr Ink jet ink compositions
US6265458B1 (en) 1998-09-28 2001-07-24 Kimberly-Clark Worldwide, Inc. Photoinitiators and applications therefor
US6368396B1 (en) 1999-01-19 2002-04-09 Kimberly-Clark Worldwide, Inc. Colorants, colorant stabilizers, ink compositions, and improved methods of making the same
US6331056B1 (en) 1999-02-25 2001-12-18 Kimberly-Clark Worldwide, Inc. Printing apparatus and applications therefor
US6294698B1 (en) 1999-04-16 2001-09-25 Kimberly-Clark Worldwide, Inc. Photoinitiators and applications therefor
US6368395B1 (en) 1999-05-24 2002-04-09 Kimberly-Clark Worldwide, Inc. Subphthalocyanine colorants, ink compositions, and method of making the same
CN102329524A (zh) * 2011-06-28 2012-01-25 淮阴工学院 一种基于凹凸棒石固载的高耐候性复合颜料的制备方法
US9399716B2 (en) 2013-07-02 2016-07-26 Chromatic Technologies Inc. Yellow thermochromic dyes, inks composition and level indicators
JP2016527345A (ja) * 2013-07-02 2016-09-08 クロマティック テクノロジーズ インコーポレイテッドＣｈｒｏｍａｔｉｃ Ｔｅｃｈｎｏｌｏｇｉｅｓ， Ｉｎｃ． 黄色サーモクロミック染料、インキ組成物およびレベルインジケーター
US9745487B2 (en) 2013-07-02 2017-08-29 Chromatic Technologies, Inc. Yellow thermochromic dyes, inks composition and level indicators
US9580603B2 (en) 2013-09-27 2017-02-28 Chromatic Technologies, Inc. Red thermochromic dyes and their ink compositions

Also Published As

Publication number Publication date
ES369481A1 (es) 1971-06-01
IE33222L (en) 1970-01-15
GB1264636A (enrdf_load_stackoverflow) 1972-02-23
IE33222B1 (en) 1974-04-17

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