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GB1405701A - Thermochromic materials - Google Patents

Thermochromic materials

Info

Publication number
GB1405701A
GB1405701A GB4317673A GB4317673A GB1405701A GB 1405701 A GB1405701 A GB 1405701A GB 4317673 A GB4317673 A GB 4317673A GB 4317673 A GB4317673 A GB 4317673A GB 1405701 A GB1405701 A GB 1405701A
Authority
GB
United Kingdom
Prior art keywords
thermochromic
polyethylene
examples
polymer
resin
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
Application number
GB4317673A
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.)
Pilot Ink Co Ltd
Original Assignee
Pilot Ink 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 Pilot Ink Co Ltd filed Critical Pilot Ink Co Ltd
Priority to GB4317673A priority Critical patent/GB1405701A/en
Publication of GB1405701A publication Critical patent/GB1405701A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00Inks
    • C09D11/50Sympathetic, colour changing or similar inks
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K9/00Use of pretreated ingredients
    • C08K9/10Encapsulated ingredients
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00Diaryl- or thriarylmethane dyes
    • C09B11/04Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10Amino derivatives of triarylmethanes
    • C09B11/24Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/26Thermosensitive paints
    • 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
    • B41M5/26Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/30Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
    • B41M5/305Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers with reversible electron-donor electron-acceptor compositions

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

1405701 Thermochromic polymer compositions PILOT INK CO Ltd 13 Sept 1973 43176/73 Headings C3B C3F C3P and C3R [Also in Divisions C4-C5 and B6] Polymers, polymer-based and cellulose-based compositions can be compounded with a thermochromic material comprising (A) at least one electron-donating chromatic organic compound selected from fluoran leuco compounds, triphenylmethane phthalide leuco compounds and lactam leuco compounds, (B) at least one compound having a phenolic hydroxyl group, and (C) at least one alcohol, ester, ketone or ether. The material will undergo reversible metachromatism in the range -100‹ to 200‹ C., the temperature of metachromatism being controlled by selection of (C), the colour being due to (A) and the phenomenon of metachromatism being initiated by (B). Compound (A) may be a diaryl phthalide, polyaryl carbinol, leuco-, acyl-, or aryl-auramine, Rhodamine B lactam, indoline, spiropyrane or fluoran. Compound (B) may be a phenol-formaldehyde resin, or a non- polymeric phenolic compound. The thermochromic material may be formulated into thermochromic polymers, inks, writing instruments, paints or sheets. In one embodiment the thermochromic material is microencapsulated (Examples 63-73), e.g. in polyurethane, polyepoxide, polyester, styrene-divinyl benzene copolymer, aminoplast, or gelatine/gum/formalin and it may then be mixed with microcapsules containing different thermochromic compositions to obtain a composition which gives rise to multiple colour changes. Thermochromic polymers.-The thermochromic material may be incorporated in a polymer in an amount 0À1-40% by wt. of the resulting composition, which may be a block, film, filaments, fine particles, elastomer or liquid. Examples 74-82 disclose thermochromic polymers as follows: 74, 78, polyethylene ; 75, polypropylene; 76, polystyrene; 77, a hydrocarbon resin; 79, polymethyl methacrylate; 80, a polyurethane; 81, an epoxy resin; 82, an unsaturated polyester. Thermochromic polymer-based compositions (1) Inks.-Example 85 is a gravure ink containing a hydrogenated hydrocarbon resin, toluene and methyl-i-butylketone; Example 94 is a ball-pen ink containing a terpene resin, triaryl-dimethane isomers and dioctyl phthalate. (2) Writing instruments.-Example 92 is a pencil lead containing polyethylene, and glass beads; Example 97 is a tube colour containing aqueous polyvinyl alcohol, and polyvinyl acetate emulsion. (3) Paints.-Examples 99-107 disclose thermochromic paints containing the following polymers and, in most cases, conventional solvents: 99, polyethylene + ethylene-vinyl acetate copolymer; 100, polyethylene + terpene resin; 101, terpene resin; 102, chlorinated rubber; 103, maleic anhydride-styrene copolymer; 104, polyvinyl acetate emulsion; 105, rosinmodified maleic resin; 106, an epoxy resin; 107, vinyl chloride-vinyl acetate copolymer; 108 and 109 are polyethylene and polypropylene powder paints. (4) Sheets.-Examples 110-117 disclose the preparation of thermochromic sheets, a first thermochromic layer comprising various polymer-based coatings, and in some cases a second protective polymer layer being superposed thereon. Thermochromic cellulose-based compositions Examples 88, 89 disclose inks; 88 contains aqueous methyl cellulose, and vinyl acetate emulsion; 89 contains ethyl cellulose in xylol and n-butyl acetate. Examples 110, 112 disclose sheets; 110 is a paper sheet coated first with aqueous methyl cellulose and vinyl acetate emulsion (and the thermochromic material), and then with a polyethylene film; 112 is a glass sheet coated first with ethyl cellulose in xylol and n-butyl acetate, and then with polyvinyl butyral.
GB4317673A 1973-09-13 1973-09-13 Thermochromic materials Expired GB1405701A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB4317673A GB1405701A (en) 1973-09-13 1973-09-13 Thermochromic materials

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4317673A GB1405701A (en) 1973-09-13 1973-09-13 Thermochromic materials

Publications (1)

Publication Number Publication Date
GB1405701A true GB1405701A (en) 1975-09-10

Family

ID=10427642

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4317673A Expired GB1405701A (en) 1973-09-13 1973-09-13 Thermochromic materials

Country Status (1)

Country Link
GB (1) GB1405701A (en)

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2494707A1 (en) * 1980-11-27 1982-05-28 Pilot Ink Co Ltd THERMOCHROMIC MATERIALS
US4362645A (en) * 1978-09-28 1982-12-07 Akzona, Inc. Temperature indicating compositions of matter
JPS587671U (en) * 1981-07-07 1983-01-18 株式会社松井色素化学工業所 Transfer printing sheet
JPS5832671A (en) * 1981-08-21 1983-02-25 Matsui Shikiso Kagaku Kogyosho:Kk Thermally reversible color changing ink composition
GB2116577A (en) * 1981-12-25 1983-09-28 Pentel Kk Ink and eraser of ink
US4407960A (en) * 1980-06-25 1983-10-04 American Sterilizer Company Visual chemical indicating composition for monitoring sterilization
GB2170228A (en) * 1985-01-30 1986-07-30 Pilot Ink Co Ltd Thermochromic textile material
US4666949A (en) * 1986-01-31 1987-05-19 Matsui Shikiso Chemical Co., Ltd. Thermochromic polyurethane foam
GB2184450A (en) * 1984-06-26 1987-06-24 Pilot Ink Co Ltd Reversible temperature-indicating compositions
US4826550A (en) * 1985-11-28 1989-05-02 Matui Shikiso Chemical Co., Ltd. Process for preparing molded product of thermochromic polyvinyl chloride
WO2004046245A1 (en) * 2002-11-19 2004-06-03 Ward, Aylis, Haviland Improved thermosetting powder
WO2009006131A1 (en) * 2007-06-29 2009-01-08 3M Innovative Properties Company An indicating fiber
EP2322587A1 (en) 2009-11-03 2011-05-18 Basf Se Thermochromic compositions
US8329851B2 (en) 2007-06-29 2012-12-11 3M Innovative Properties Company Functional polymer with a pendant color changing indicator
WO2013106420A1 (en) * 2012-01-09 2013-07-18 Chromatic Technologies, Inc. Reversible thermochromic and photochromic ink pens and markers
WO2013115800A1 (en) * 2012-01-31 2013-08-08 Chromatic Technologies, Inc. Thermochromic systems with controlled hysteresis
WO2015135949A1 (en) * 2014-03-13 2015-09-17 Se Bel Lee Yun Emulsion comprising microencapsulated thermochromic leuco colorants and method for multi-microencapsulation
US9493668B2 (en) 2012-01-09 2016-11-15 Chromatic Technologies, Inc. Reversible thermochromic and photochromic ink pens and markers
CN112852402A (en) * 2020-12-22 2021-05-28 厦门安踏体育用品有限公司 Durable thermochromic material, preparation method thereof and application thereof in textiles
CN114716980A (en) * 2022-04-18 2022-07-08 桂林电子科技大学 Reversible thermochromic functional composite phase change material and preparation method and application thereof
CN115851256A (en) * 2022-09-21 2023-03-28 东南大学 Reversible thermochromic material and preparation method thereof
CN116144219A (en) * 2023-04-17 2023-05-23 北京高德品创科技有限公司 Thermochromic anti-counterfeiting ink as well as preparation method and application thereof
CN116426163A (en) * 2023-04-04 2023-07-14 合肥金龙浩科技有限公司 Thermochromic ink and application thereof

Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4362645A (en) * 1978-09-28 1982-12-07 Akzona, Inc. Temperature indicating compositions of matter
US4407960A (en) * 1980-06-25 1983-10-04 American Sterilizer Company Visual chemical indicating composition for monitoring sterilization
FR2494707A1 (en) * 1980-11-27 1982-05-28 Pilot Ink Co Ltd THERMOCHROMIC MATERIALS
JPS587671U (en) * 1981-07-07 1983-01-18 株式会社松井色素化学工業所 Transfer printing sheet
JPS6119040Y2 (en) * 1981-07-07 1986-06-09
JPS5832671A (en) * 1981-08-21 1983-02-25 Matsui Shikiso Kagaku Kogyosho:Kk Thermally reversible color changing ink composition
JPS6228990B2 (en) * 1981-08-21 1987-06-23 Matsui Shikiso Kagaku Kogyosho
GB2116577A (en) * 1981-12-25 1983-09-28 Pentel Kk Ink and eraser of ink
GB2184450A (en) * 1984-06-26 1987-06-24 Pilot Ink Co Ltd Reversible temperature-indicating compositions
FR2592158A1 (en) * 1984-06-26 1987-06-26 Pilot Ink Co Ltd COMPOSITION INDICATING THE TEMPERATURE IN A REVERSIBLE MANNER.
GB2170228A (en) * 1985-01-30 1986-07-30 Pilot Ink Co Ltd Thermochromic textile material
AU584163B2 (en) * 1985-01-30 1989-05-18 Pilot Ink Co. Ltd. Thermochromic textile material
GB2170228B (en) * 1985-01-30 1989-07-05 Pilot Ink Co Ltd Thermochromic textile material
US4826550A (en) * 1985-11-28 1989-05-02 Matui Shikiso Chemical Co., Ltd. Process for preparing molded product of thermochromic polyvinyl chloride
US4666949A (en) * 1986-01-31 1987-05-19 Matsui Shikiso Chemical Co., Ltd. Thermochromic polyurethane foam
GB2396156A (en) * 2002-11-19 2004-06-16 Ward Aylis Haviland Thermosetting powder
WO2004046245A1 (en) * 2002-11-19 2004-06-03 Ward, Aylis, Haviland Improved thermosetting powder
WO2009006131A1 (en) * 2007-06-29 2009-01-08 3M Innovative Properties Company An indicating fiber
US8329851B2 (en) 2007-06-29 2012-12-11 3M Innovative Properties Company Functional polymer with a pendant color changing indicator
EP2322587A1 (en) 2009-11-03 2011-05-18 Basf Se Thermochromic compositions
US9676953B2 (en) 2012-01-09 2017-06-13 Chromatic Technologies, Inc. Reversible thermochromic and photochromic ink pens and markers
US9493668B2 (en) 2012-01-09 2016-11-15 Chromatic Technologies, Inc. Reversible thermochromic and photochromic ink pens and markers
WO2013106420A1 (en) * 2012-01-09 2013-07-18 Chromatic Technologies, Inc. Reversible thermochromic and photochromic ink pens and markers
US9777178B2 (en) 2012-01-09 2017-10-03 Chromatic Technologies, Inc. Reversible thermochromic and photochromic ink pens and markers
WO2013115800A1 (en) * 2012-01-31 2013-08-08 Chromatic Technologies, Inc. Thermochromic systems with controlled hysteresis
WO2015135949A1 (en) * 2014-03-13 2015-09-17 Se Bel Lee Yun Emulsion comprising microencapsulated thermochromic leuco colorants and method for multi-microencapsulation
CN112852402A (en) * 2020-12-22 2021-05-28 厦门安踏体育用品有限公司 Durable thermochromic material, preparation method thereof and application thereof in textiles
CN112852402B (en) * 2020-12-22 2023-06-23 厦门安踏体育用品有限公司 Durable thermochromic material, preparation method thereof and application thereof in textiles
CN114716980A (en) * 2022-04-18 2022-07-08 桂林电子科技大学 Reversible thermochromic functional composite phase change material and preparation method and application thereof
CN115851256A (en) * 2022-09-21 2023-03-28 东南大学 Reversible thermochromic material and preparation method thereof
CN116426163A (en) * 2023-04-04 2023-07-14 合肥金龙浩科技有限公司 Thermochromic ink and application thereof
CN116144219A (en) * 2023-04-17 2023-05-23 北京高德品创科技有限公司 Thermochromic anti-counterfeiting ink as well as preparation method and application thereof
CN116144219B (en) * 2023-04-17 2023-07-11 北京高德品创科技有限公司 Thermochromic anti-counterfeiting ink as well as preparation method and application thereof

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Legal Events

Date Code Title Description
PS Patent sealed
PE20 Patent expired after termination of 20 years

Effective date: 19930912