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WO2019107263A1 - Composé de pigment et feuille d'impression par transfert thermosensible - Google Patents

Composé de pigment et feuille d'impression par transfert thermosensible Download PDF

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Publication number
WO2019107263A1
WO2019107263A1 PCT/JP2018/043108 JP2018043108W WO2019107263A1 WO 2019107263 A1 WO2019107263 A1 WO 2019107263A1 JP 2018043108 W JP2018043108 W JP 2018043108W WO 2019107263 A1 WO2019107263 A1 WO 2019107263A1
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WIPO (PCT)
Prior art keywords
group
formula
dye
compound
sulfonic 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.)
Ceased
Application number
PCT/JP2018/043108
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English (en)
Japanese (ja)
Inventor
愛 早川
真範 関
城田　衣
元 牟田
太一 新藤
三東　剛
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.)
Canon Inc
Original Assignee
Canon 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
Priority claimed from JP2018197292A external-priority patent/JP6594513B2/ja
Application filed by Canon Inc filed Critical Canon Inc
Publication of WO2019107263A1 publication Critical patent/WO2019107263A1/fr
Priority to US16/879,035 priority Critical patent/US11958978B2/en
Anticipated expiration legal-status Critical
Ceased 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
    • B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
    • B41M5/382—Contact thermal transfer or sublimation processes
    • B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
    • 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
    • B41M5/382—Contact thermal transfer or sublimation processes
    • B41M5/385—Contact thermal transfer or sublimation processes characterised by the transferable dyes or pigments
    • B41M5/39—Dyes containing one or more carbon-to-nitrogen double bonds, e.g. azomethine
    • 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
    • C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus

Definitions

  • the thermal transfer recording method is excellent in that printing can be performed by a dry process, miniaturization is possible, and portability of the printer is excellent, and printing can be performed easily regardless of the surrounding environment.
  • a dye is used as a color material, the density of the image can be expressed by the density gradation of the color material, so that the sharpness and the color reproducibility of the image are excellent.
  • an image is recorded by transferring a dye in the thermal transfer recording sheet to the image receiving sheet by superposing the thermal transfer recording sheet on the image receiving sheet and heating the thermal transfer recording sheet.
  • the thermal transfer recording sheet has a color material layer containing a thermally transferable dye on a sheet-like substrate, and the image receiving sheet has a dye receiving layer on the surface.
  • the colorant contained in the colorant layer is a very important material because it affects the speed of transfer recording, the image quality of the recorded matter, and the storage stability.
  • the colorant to be used is required to have excellent light fastness and dispersibility (at the time of ink sheet preparation), and therefore it is required to be excellent in light fastness and dispersibility as well as having high chroma.
  • anthraquinone compounds are known (Patent Document 1).
  • the problem is that anthraquinone compounds have low saturation.
  • triphenylmethane compounds have vivid color forming properties, and there is a proposal to use these in heat-meltable inks (also referred to as phase change inks and hot melt inks) (Patent Document 1) 2).
  • the application of the triphenylmethane compound to a thermal transfer recording sheet has not been described.
  • An object of the present invention is to provide a dye compound having high chroma, high light fastness and excellent dispersibility.
  • Another object of the present invention is to provide a thermal transfer recording sheet capable of obtaining an image having high saturation and high light resistance.
  • R 1 and R 2 each independently represent a substituted alkyl group or a non-substituted alkyl group
  • R 3 and R 4 each independently represent a hydrogen atom, an alkyl group having a substituent, an unsubstituted alkyl group, an aryl group having a substituent, or an unsubstituted aryl group
  • R 5 and R 6 each independently represent a hydrogen atom or an unsubstituted alkyl group having 1 to 4 carbon atoms
  • R 7 and R 8 each independently represent an unsubstituted alkyl group having 1 to 4 carbon atoms
  • R 9 represents a halogen atom, a nitro group, a sulfo group, a sulfonic acid ester group, a sulfonamide group, a sulfonic acid group, a benzenesulfonyl group, a trifluoromethylsulfonyl group or a perfluoroal
  • R 1 ⁇ R 8 have the same meanings as R 1 ⁇ R 8 in the formula (1-1).
  • R 9 ′ represents a sulfonato group
  • R 10 ′ represents a hydrogen atom, a halogen atom, a nitro group, a sulfo group, a sulfonic acid ester group, a sulfonamide group, a sulfonic acid group, a benzenesulfonyl group, a trifluoromethylsulfonyl group, or a perfluoroalkyl group.
  • the present invention is also a thermal transfer recording sheet comprising a substrate and a coloring material layer on the substrate,
  • the colorant layer has at least a yellow dye layer containing a yellow dye, a magenta dye layer containing a magenta dye, and a cyan dye layer containing a cyan dye,
  • the present invention relates to a thermal transfer recording sheet, wherein the cyan dye is a dye compound having a structure represented by the above formula (1-1) or formula (1-2).
  • the dye compound it is possible to provide a thermal transfer recording sheet having high chroma and high light resistance.
  • FIG. 2 is a cross-sectional view showing an outline of a thermal transfer recording sheet used in Example 1;
  • R 1 and R 2 each independently represent a substituted alkyl group or a non-substituted alkyl group
  • R 3 and R 4 each independently represent a hydrogen atom, an alkyl group having a substituent, an unsubstituted alkyl group, an aryl group having a substituent, or an unsubstituted aryl group
  • R 5 and R 6 each independently represent a hydrogen atom or an unsubstituted alkyl group having 1 to 4 carbon atoms
  • R 7 and R 8 each independently represent an unsubstituted alkyl group having 1 to 4 carbon atoms
  • R 9 represents a halogen atom, a nitro group, a sulfo group, a sulfonic acid ester group, a sulfonamide group, a sulfonic acid group, a benzenesulfonyl group, a trifluoromethylsulfonyl group or a perfluoroal
  • R 1 ⁇ R 8 have the same meanings as R 1 ⁇ R 8 in the formula (1-1).
  • R 9 ′ represents a sulfonato group
  • R 10 ′ represents a hydrogen atom, a halogen atom, a nitro group, a sulfo group, a sulfonic acid ester group, a sulfonamide group, a sulfonic acid group, a benzenesulfonyl group, a trifluoromethylsulfonyl group, or a perfluoroalkyl group.
  • the compound of the present invention has at least the substituents R 7 and R 8 and the substituents R 1 and R 2 bonded to the nitrogen atom, and due to the effects of these substituents, the steric twisted structure in the molecule is It is formed. Therefore, intramolecular or intermolecular interactions are suppressed by the effect of steric twist, and aggregation of the compound can be suppressed. Therefore, the high dispersion state is maintained and the high saturation is achieved. On the other hand, we believe that the three-dimensional twisted structure will be highly lightfast because it protects the carbon atoms in the center that are susceptible to attack. When all of R 1 to R 4 are hydrogen atoms, they are easily affected by light and are inferior in light resistance.
  • the unsubstituted alkyl group in R 1 , R 2 , R 3 and R 4 is not particularly limited, but it is linear or branched. Or a cyclic alkyl group having 1 to 20 carbon atoms.
  • ethyl group, n-butyl group, sec-butyl group, dodecyl group, cyclohexyl group, methylcyclohexyl group, 2-ethylpropyl group, 2-ethylhexyl group and octyl group are preferable. More preferably, it is n-butyl group, 2-ethylhexyl group or octyl group. Further, it is preferable that R 1 and R 2 are the same alkyl group, and R 3 and R 4 are a hydrogen atom or the same alkyl group, because they are excellent in high chroma, high dispersion, and high light resistance.
  • the substituent of the alkyl group having a substituent in R 1 , R 2 , R 3 and R 4 in formulas (1-1) and (1-2) is not particularly limited, but is preferably a phenyl group , Cyano group, halogen atom (fluorine atom, chloro atom, etc.), nitro group, salt of sulfonic acid group (sulfonic acid sodium salt etc.), sulfo group (-SO 3 H), sulfonic acid ester group (sulfonic acid methyl group etc.) And a perfluoroalkyl group (perfluoromethyl group, perfluoroethyl group etc.), an alkoxy group (methoxy group, ethoxy group etc.), a trifluoromethylsulfonyl group etc.
  • a phenyl group or a cyano group is preferable because a compound having high chroma, high light resistance and excellent dispersibility can be obtained.
  • examples of the unsubstituted aryl group in R 3 and R 4 include, but not particularly limited to, a phenyl group and a naphthyl group.
  • the substituent of the aryl group having a substituent in R 3 and R 4 in formulas (1-1) and (1-2) is not particularly limited, and alkyl such as methyl group and ethyl group is not particularly limited.
  • alkyl such as methyl group and ethyl group is not particularly limited.
  • Groups, alkoxy groups such as methoxy group and ethoxy group, salts of sulfonic acid groups such as cyano group, sulfonic acid sodium salt, and sulfonic acid groups.
  • R 9 and R 10 each represent a sulfo group; a sulfonic acid ester group such as a sulfonic acid methyl group or a sulfonic acid ethyl group; a sulfonamide group, an N-methyl sulfonamide group, N, N-dimethyl Sulfonamide group, N-ethyl sulfonamide group, N, N-diethyl sulfonamide group, N-propyl sulfonamide group, N, N-dipropyl sulfonamide group, N-butyl sulfonamide group, N, N-dibutyl sulfone group Amide group, N-pentyl sulfonamide group, N, N-dipentyl sulfonamide group, N-hexyl sulfonamide group, N, N- dihexyl sulfonamide group, N-oc
  • Benzenesulfonyl group trifluoromethylsulfonyl group etc. It is also good. Among them, a sulfo group and a sulfonic acid sodium salt are more preferable because they are excellent in high chroma, high dispersion, and high light resistance.
  • the perfluoroalkyl group for R 9 and R 10 in the formula (1-1) is not particularly limited, but a perfluoromethyl group, a perfluoroethyl group, a perfluoroisopropyl group, a perfluoro n-butyl group Groups, perfluorooctyl groups and the like.
  • a perfluoromethyl group is more preferable because it is excellent in high chroma, high dispersion, and high light resistance.
  • X - as the anion but are not limited to, fluorine ion, chlorine ion, bromine ion, iodine ion, cyanide ion, nitrate ion, benzenesulfonate ion, p- Toluene sulfonate ion, methyl sulfate ion, ethyl sulfate ion, propyl sulfate ion, tetrafluoroborate ion, tetraphenylborate ion, benzenesulfinate ion, acetate ion, trifluoroacetate ion, propionacetate ion, benzoate ion, Oxalate ion, succinate ion, malonate ion, oleate ion, stearate ion, citrate ion, picolinate ion, monohydrogen diphosphate
  • the compounds represented by (A37) and (A37) are preferred as cyan dyes.
  • (A3), (A7), (A11), (A15), (A23), (A25), (A29), (A30), (A34) are excellent in high saturation, high dispersion, and high light resistance. , More preferred.
  • the cation may be present in a delocalized manner, and the cation site may be present at any position in the molecule, either of which is present. It is a category of invention.
  • the structure changes as follows.
  • the compounds represented by the general formula (1-1) or the formula (1-2) can be synthesized based on known methods. That is, the compound represented by the general formula (1-1) or the formula (1-2) is a condensation step of condensing the compounds (A), (B) and (C) to obtain the compound (D), and then It can synthesize
  • the condensation step and the oxidation step can be carried out, if necessary, in the presence of a liquid medium, a condensing agent, an oxidizing agent and the like.
  • condensation step First, the condensation step will be described.
  • the condensation step can be carried out in the presence of a medium, a condensing agent, an oxidizing agent and the like, if necessary.
  • the condensation step can also be carried out without solvent, but it is preferred to use a medium.
  • the amount of the reaction solvent used is preferably 0.1 to 1000% by mass, and more preferably 1.0 to 150% by mass, based on the aldehyde compound (C).
  • the condensing agent that can be used in the condensation step is not particularly limited, and examples thereof include sulfuric acid, hydrochloric acid, phosphoric acid, acetic acid, formic acid, aluminum chloride, zinc chloride, p-toluenesulfonic acid and the like. Particularly preferred are sulfuric acid, hydrochloric acid and acetic acid.
  • the amount of the above-mentioned condensing agent used is preferably 0.01 to 20% by mass, more preferably 0.1 to 10% by mass, with respect to the aldehyde compound (C).
  • the reaction temperature in the condensation step can be in the range of 0 to 160 ° C.
  • the temperature is preferably 50 ° C. to 140 ° C., more preferably 60 ° C. to 120 ° C.
  • This condensation reaction is usually completed within 24 hours, and after completion of the reaction, purification by column purification or crystallization can be performed.
  • the oxidation step can be carried out in the presence of a medium, an oxidant and the like, if necessary.
  • the oxidation step can be carried out without solvent, but it is preferred to use a medium.
  • the amount of the reaction solvent used is preferably 0.1 to 1000% by mass, and more preferably 1.0 to 200% by mass, based on the aldehyde compound (C).
  • the amount of the oxidizing agent used is preferably 0.01 to 20% by mass, and more preferably 0.1 to 5% by mass, based on the aldehyde compound (C).
  • the pH of the medium in the oxidation step is preferably pH 1-9, more preferably pH 2-8, especially pH 3-7.
  • the reaction temperature in the oxidation step can be in the range of 0 to 150 ° C.
  • the temperature is preferably 10 ° C to 100 ° C, and particularly preferably 20 ° C to 80 ° C.
  • the oxidation reaction is usually completed within 18 hours, and after completion of the reaction, purification by column purification or crystallization can be performed.
  • the compounds represented by the above general formulas (1-1) and (1-2) may be used alone or in combination of two or more in order to adjust the color tone or the like according to the application. You may use together. Furthermore, it can also be used in combination with known dyes. Two or more kinds of known dyes may be combined.
  • each of R 11 to R 15 independently represents an alkyl group, an aryl group having a substituent, or an unsubstituted aryl group.
  • the aryl group having a substituent in R 11 to R 15 or the unsubstituted aryl group is not particularly limited, but R 3 and R 4 in the above Formula (1-1) may be used. And the same groups as those exemplified as the substituted or unsubstituted aryl group in the above.
  • R 16 and R 17 each independently represent an alkyl group, an aryl group having a substituent, or an unsubstituted aryl group.
  • Examples of the alkyl group in R 16 and R 17 in the formula (3) include the same groups as those exemplified as the alkyl group in R 1 , R 2 , R 3 and R 4 in the above formula (1-1). .
  • an alkyl group having 1 to 2 carbon atoms such as a methyl group or an ethyl group, it is preferable because it is excellent in high chroma, high dispersion, and high light resistance.
  • the aryl group having a substituent or the unsubstituted aryl group in R 16 and R 17 in the formula (3) is not particularly limited, and examples thereof include a phenyl group and a naphthyl group. In particular, when a phenyl group is used, it is preferable because it is excellent in high chroma, high dispersion, and high light resistance.
  • Examples of the substituent of the substituted aryl group include an alkyl group and an alkoxy group.
  • compounds (C3), (C4) and (C5) are preferred as cyan dyes. From the viewpoint of the effects of the present invention, the compound (C3) is further preferred.
  • the thermal transfer recording sheet of the present invention has a substrate and a colorant layer on the substrate.
  • the color material layer includes at least a yellow dye layer containing a yellow dye, a magenta dye layer containing a magenta dye, and a cyan dye layer containing a cyan dye.
  • Image formation using a thermal transfer recording sheet is performed as follows.
  • the substrate constituting the heat-sensitive transfer recording sheet according to the present invention supports the later-described color material layer, and a known substrate can be used.
  • the material is not particularly limited as long as it has a certain degree of heat resistance and strength, and examples thereof include the following.
  • Polyethylene terephthalate film polyethylene naphthalate film, polycarbonate film, polyimide film, polyamide film, aramid film, polystyrene film, 1,4-polycyclohexylene dimethylene terephthalate film, polysulfone film, polypropylene film, polyphenylene sulfide film, polyvinyl alcohol film , Cellophane, cellulose derivative, polyethylene film, polyvinyl chloride film, nylon film, condenser paper, paraffin paper.
  • polyethylene terephthalate film is preferred in view of mechanical strength, solvent resistance and economy.
  • the adhesion treatment is not particularly limited, and examples thereof include ozone treatment, corona discharge treatment, ultraviolet treatment, plasma treatment, low temperature plasma treatment, primer treatment, chemical treatment and the like. Also, two or more of these processes may be combined.
  • an adhesion layer may be coated on the substrate.
  • Organic materials such as polyester resin, polystyrene resin, polyacrylic ester resin, polyamide resin, polyether resin, polyvinyl acetate resin, polyethylene resin, polypropylene resin, polyvinyl chloride resin, polyvinyl alcohol resin, polyvinyl butyral resin.
  • Inorganic fine particles such as silica, alumina, magnesium carbonate, magnesium oxide and titanium oxide.
  • the thermal transfer recording sheet has a colorant layer on a substrate.
  • the color material layer has at least a yellow dye layer, a magenta dye layer and a cyan dye layer.
  • a conventionally known black dye layer may be added as a dye layer to the thermal transfer recording sheet.
  • a compound having a structure represented by the above formula (1-1) or formula (1-2) is used as the cyan dye to be contained in the cyan dye layer.
  • the dye is not particularly limited as long as it is a dye that is conventionally known and used for thermal transfer and is subjected to sublimation transfer by heat, and the hue, printing sensitivity, light resistance, storage stability, binding It can be appropriately selected and used in consideration of the solubility in the resin and the like.
  • Each dye layer contains each dye dye and a binder resin, and the method for forming each dye layer is not particularly limited, but it is usually produced as follows.
  • the amount of each color dye used is 50 to 300 parts by mass, preferably 80 to 280 parts by mass, and further 85 to 250 parts by mass with respect to 100 parts by mass of the binder resin. Preferred.
  • the amount used corresponds to the mass part of the total amount of the respective dyestuffs when two or more dyes are used in combination.
  • a surfactant may be contained in the heat-sensitive transfer recording sheet in order to provide sufficient lubricity at the time of heating the thermal head (during printing).
  • Surfactants that can be added include cationic surfactants, anionic surfactants, and nonionic surfactants.
  • cationic surfactants Dodecyl ammonium chloride, dodecyl ammonium bromide, dodecyl trimethyl ammonium bromide, dodecyl pyridinium chloride, dodecyl pyridinium bromide, hexadecyl trimethyl ammonium bromide.
  • nonionic surfactants include the following. Dodecyl polyoxyethylene ether, hexadecyl polyoxyethylene ether, nonylphenyl polyoxyethylene ether, lauryl polyoxyethylene ether, sorbitan monooleate polyoxyethylene ether, monodecanoyl sucrose.
  • the thermal transfer recording sheet may contain a wax to have sufficient lubricity when the thermal head is not heated.
  • Waxes that can be added include, but are not limited to, polyethylene wax, paraffin wax, fatty acid ester wax.
  • an ultraviolet absorber an antiseptic, an antioxidant, an antistatic agent, and a viscosity modifier may be added to the thermal transfer recording sheet in addition to the above-described additives.
  • the heat-sensitive transfer recording sheet has a heat-resistant slip layer on the surface opposite to the surface on which the coloring material layer is provided, for the purpose of improving heat resistance and runnability of the thermal head. Is preferably provided.
  • the heat resistant slip layer is formed of a heat resistant resin.
  • the heat-resistant resin is not particularly limited, and examples thereof include the following. Polyvinyl butyral resin, polyvinyl acetal resin, polyester resin, polyether resin, polybutadiene resin, vinyl chloride-vinyl acetate copolymer resin, styrene-butadiene copolymer resin, polyurethane acrylate, polyester acrylate, polyimide resin, polycarbonate resin.
  • a lubricant, a crosslinking agent, a mold release agent, heat resistant fine particles and the like may be further added to the heat resistant slip layer.
  • the lubricants include amino-modified silicone compounds and carboxy-modified silicone compounds. Further, as the heat resistant fine particles, fine particles such as silica may be mentioned, and as the binding agent, acrylic resin may be mentioned, however, it is not limited to these.
  • the heat-resistant slip layer is formed by applying a heat-resistant slip layer coating solution prepared by adding the above-mentioned resin and additive to a solvent and dissolving or dispersing it.
  • a heat-resistant slip layer coating solution prepared by adding the above-mentioned resin and additive to a solvent and dissolving or dispersing it.
  • coat a heat-resistant lubricating layer coating liquid The method using a bar coater, a gravure coater, a reverse roll coater, a rod coater, an air doctor coater is mentioned.
  • a method using a gravure coater is preferred.
  • the coating amount of the heat resistant slipping layer coating solution is preferably such that the thickness of the color material layer after drying is in the range of 0.1 ⁇ m to 5 ⁇ m from the viewpoint of transferability.
  • the heating means for heating the thermal transfer recording sheet is not particularly limited, but not only a conventional method using a thermal head but also infrared rays or laser light can be used. Moreover, it can also heat by supplying electricity to base film itself. In this case, a conductive dye transfer sheet may be formed using a conductive heat generating film that generates heat.
  • Identification of the obtained compound includes 1 H nuclear magnetic resonance spectroscopy ( 1 H-NMR) apparatus (AVANCE-600 NMR spectrometer, manufactured by BRUKER), and MALDI-TOF / MS (MALDI-TOF / MS ultraFleXtreme, BRUKER) Company) equipment.
  • 1 H-NMR 1 H nuclear magnetic resonance spectroscopy
  • AVANCE-600 NMR spectrometer manufactured by BRUKER
  • MALDI-TOF / MS MALDI-TOF / MS ultraFleXtreme, BRUKER
  • Cyan ink (C2) to (C6) in the same manner as in Cyan ink preparation example 1 except that compound (A3) was changed to the cyan dye (the compound of the present invention and the comparative compound) shown in Table 1 I got C4).
  • Example 1 As a substrate, a polyethylene terephthalate film (Lumirror (registered trademark); manufactured by Toray Industries, Inc.) having a thickness of 4.5 ⁇ m is used.
  • the cyan ink (C1) was applied onto the substrate so that the thickness after drying was 1 ⁇ m, and the cyan ink layer was formed by drying.
  • the thermal transfer recording sheet having yellow dye layer Y, magenta dye layer M, cyan dye layer C, and protective layer 4 color ink KL-36IP for compact photo printer SELPHY CP1200 manufactured by Canon Inc.
  • the cyan dye layer was cut out.
  • a cyan dye layer formed using the above-mentioned cyan ink (C1) of the same size (width, length and thickness) as the cut-out cyan dye layer is stuck to obtain full color feeling.
  • a thermal transfer recording sheet was formed.
  • the obtained sheet for thermal transfer recording was transferred to a printing paper by a Selphy remodeler to prepare an image sample (1). As an image, the output was adjusted so that the optical density (OD) became 1.0, and cyan was printed in a single color.
  • Image samples (2) to (16) and comparative image samples (1) to (8) were prepared in the same manner as in Example 1 using each of the prepared thermal transfer recording sheets, and evaluations described later were performed. The The evaluation results are shown in Table 2.
  • the evaluation criteria are as follows. A: C * is 45.0 or more B: C * is 35.0 or more and less than 45.0 C: C * is less than 35.0
  • Evaluation criteria are as follows. A: 60 ⁇ O. D. Survival rate(%) B: 50 ⁇ O. D. Residual rate (%) ⁇ 60 C: O. D. Residual rate (%) ⁇ 50
  • the evaluation criteria are as follows. A: Almost no compound aggregates are observed B: Some compound aggregates are confirmed C: A lot of compound aggregates are confirmed

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  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)

Abstract

La présente invention utilise un composé à base de triphénylméthane ayant un substituant spécifique.
PCT/JP2018/043108 2017-11-29 2018-11-22 Composé de pigment et feuille d'impression par transfert thermosensible Ceased WO2019107263A1 (fr)

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US16/879,035 US11958978B2 (en) 2017-11-29 2020-05-20 Coloring compound and thermal transfer recording sheet

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JP2017229293 2017-11-29
JP2017-229293 2017-11-29
JP2018197292A JP6594513B2 (ja) 2017-11-29 2018-10-19 色素化合物及び感熱転写記録用シート
JP2018-197292 2018-10-19

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11958978B2 (en) 2017-11-29 2024-04-16 Canon Kabuskiki Kaisha Coloring compound and thermal transfer recording sheet

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US3538105A (en) * 1965-02-26 1970-11-03 Mitsubishi Chem Ind Novel triarylmethane dyestuffs
JPS52113739A (en) * 1976-03-19 1977-09-24 Canon Inc Electrostatically developing toner
JPH09111136A (ja) * 1995-10-23 1997-04-28 Fuji Photo Film Co Ltd インドリルフタリド化合物およびそれを使用した記録材料
WO2008026105A2 (fr) * 2006-08-31 2008-03-06 Kimberly-Clark Worldwide, Inc. Procédé de détection de candida sur la peau
JP2015178270A (ja) * 2014-02-28 2015-10-08 キヤノン株式会社 感熱転写記録用シート

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3538105A (en) * 1965-02-26 1970-11-03 Mitsubishi Chem Ind Novel triarylmethane dyestuffs
JPS52113739A (en) * 1976-03-19 1977-09-24 Canon Inc Electrostatically developing toner
JPH09111136A (ja) * 1995-10-23 1997-04-28 Fuji Photo Film Co Ltd インドリルフタリド化合物およびそれを使用した記録材料
WO2008026105A2 (fr) * 2006-08-31 2008-03-06 Kimberly-Clark Worldwide, Inc. Procédé de détection de candida sur la peau
JP2015178270A (ja) * 2014-02-28 2015-10-08 キヤノン株式会社 感熱転写記録用シート

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Title
ARIENT, JOSEF ET AL.: "Triphenylmethane dyes. I. Condensation of N-methylcumidine with formaldehyde, Michler's ketone, and o- chlorobenzaldehyde", COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, vol. 22, 1957, pages 468 - 472 *

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US11958978B2 (en) 2017-11-29 2024-04-16 Canon Kabuskiki Kaisha Coloring compound and thermal transfer recording sheet

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