WO2014181763A1 - Composition de développement de couleur thermosensible et matériau de publication thermosensible l'utilisant - Google Patents

Composition de développement de couleur thermosensible et matériau de publication thermosensible l'utilisant Download PDF

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WO2014181763A1
WO2014181763A1 PCT/JP2014/062133 JP2014062133W WO2014181763A1 WO 2014181763 A1 WO2014181763 A1 WO 2014181763A1 JP 2014062133 W JP2014062133 W JP 2014062133W WO 2014181763 A1 WO2014181763 A1 WO 2014181763A1
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group
substituted
unsubstituted
ring
groups
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文二 澤野
詫摩　啓輔
長一郎 山本
熊谷　洋二郎
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山本化成株式会社
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Priority to JP2015515864A priority Critical patent/JP6282640B2/ja
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    • 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
    • B41M5/333—Colour developing components therefor, e.g. acidic compounds
    • B41M5/3333—Non-macromolecular compounds
    • B41M5/3335—Compounds containing phenolic or carboxylic acid groups or metal salts thereof
    • 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
    • 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
    • B41M5/333—Colour developing components therefor, e.g. acidic compounds
    • B41M5/3333—Non-macromolecular compounds

Definitions

  • the present invention relates to a thermochromic composition that forms a colored body having a clear yellow to blue high density and high fastness. Furthermore, the present invention relates to a heat-sensitive recording material containing the composition.
  • Patent Documents 4 to 5 a method of using an irreversible coloring material by a thermal melting reaction between an aromatic isocyanate and an imino compound as a recording image has been proposed. There was a drawback of being low. In view of the above, there is a need for a heat-sensitive recording material that solves the conventional problems, satisfies practical color development sensitivity and storage stability of a color image at the same time, and has a clear and high density color image. In recent years, transparent thermosensitive recording materials with high transparency, high color density, and excellent image storability have been developed for applications such as medical diagnostic imaging films, image forming films for overhead projectors, and CAD image forming films. It is requested.
  • An object of the present invention is to provide a heat-sensitive color-forming composition that forms a colored body having a high concentration and a high fastness, and a heat-sensitive recording material using the composition.
  • the present invention (I) a thermosensitive coloring composition containing an imino compound represented by the general formula (1), (2) or (3) and a pyrrolinone compound represented by the general formula (4);
  • ring X represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heterocyclic ring
  • R 1 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, substituted or unsubstituted A substituted aryl group, a substituted or unsubstituted aralkyl group is shown.
  • R 2 represents a substituted or unsubstituted alkyl group
  • rings X and R 1 have the same meanings as those shown in formula (1).
  • R 3 and R 4 each independently represent a substituted or unsubstituted alkyl group, and R 3 and R 4 may combine to form a ring.
  • Ring X and R 1 have the same meanings as those shown in formula (1).
  • A represents a substituted or unsubstituted aromatic ring, a substituted or unsubstituted heterocyclic ring
  • R 5 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group.
  • a in formula (4) is substituted or unsubstituted benzene ring, substituted or unsubstituted naphthalene ring, substituted or unsubstituted anthracene ring, substituted or unsubstituted pyridine ring, substituted or unsubstituted quinoline ring , Substituted or unsubstituted pyrrole ring, substituted or unsubstituted indole ring, substituted or unsubstituted thiophene ring, substituted or unsubstituted benzothiophene ring, substituted or unsubstituted furan ring, substituted or unsubstituted benzofuran ring A thermosensitive coloring composition of (i) or (ii),
  • the present invention it has become possible to provide a heat-sensitive recording material that simultaneously satisfies vivid and high-density color development and storage stability of a color image, and a transparent heat-sensitive recording material having high transparency.
  • the present invention relates to an imino compound represented by the general formula (1), (2) or (3) (hereinafter abbreviated as “component I” in the meaning of the color former-forming component I) and the general formula (4).
  • component I an imino compound represented by the general formula (1), (2) or (3)
  • component P the pyrrolinone compound
  • Component I used in the present invention is an imino compound represented by the general formula (1), (2) or (3).
  • ring X represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heterocyclic ring
  • R 1 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, substituted or unsubstituted
  • substituted aryl group a substituted or unsubstituted aralkyl group is shown.
  • R 2 represents a substituted or unsubstituted alkyl group, and rings X and R 1 have the same meanings as those shown in formula (1).
  • R 3 and R 4 each independently represent a substituted or unsubstituted alkyl group, and R 3 and R 4 may combine to form a ring. Ring X and R 1 have the same meanings as those shown in formula (1).
  • X is preferably a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted pyridine ring.
  • X is more preferably a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted anthracene ring.
  • substituents include a halogen atom, a hydroxyl group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted group Aryl group, substituted or unsubstituted aralkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted alkyl A carbonyl group, a substituted or unsubstituted arylcarbonyl group, a substituted or unsubstituted amino group, and the like are preferable.
  • a halogen atom a hydroxyl group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted group having 1 to 20 carbon atoms.
  • substituent when X has a substituent are shown below.
  • the halogen atom include a chlorine atom, a bromine atom, a fluorine atom, and an iodine atom.
  • the substituted or unsubstituted alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and an isopentyl group.
  • Examples of the substituted or unsubstituted alkenyl group include a vinyl group, a propenyl group, a 1-butenyl group, an isobutenyl group, a 1-pentenyl group, a 2-pentenyl group, a 2-methyl-1-butenyl group, and a 2-cyclopentenyl group.
  • Examples of the substituted or unsubstituted alkynyl group include acetylenyl group, propynyl group, 1-butynyl group, 1-pentynyl group, 2-pentynyl group, 2-methyl-1-pentynyl group, and phenylacetylenyl group. It is done.
  • Examples of the substituted or unsubstituted aryl group include a phenyl group, 1-naphthyl group, 2-naphthyl group, 2-anthracenyl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 1-pyrenyl group, Unsubstituted aryl groups such as 2-pyrenyl group, 2-perylenyl group, 3-perylenyl group, 2-fluoranthenyl group, 3-fluoranthenyl group, 7-fluoranthenyl group, 8-fluoranthenyl group; 1-methyl-2-pyrenyl group, 2-methylphenyl group, 4-ethylphenyl group, 4- (4'-tert-butylcyclohexyl) phenyl group, 3-cyclohexylphenyl group, 2-cyclohexylphenyl group, 4-ethyl An aryl group substituted with an alkyl group such as a 1-na
  • Examples of the substituted or unsubstituted aralkyl group include benzyl group, ⁇ -methylbenzyl group, phenethyl group, ⁇ -methylphenethyl group, ⁇ , ⁇ -dimethylbenzyl group, ⁇ , ⁇ -dimethylphenethyl group, 4-methylphenethyl group.
  • An aralkyl group unsubstituted or substituted with an alkyl group such as a group, 4-methylbenzyl group, 4-isopropylbenzyl group
  • An aralkyl group substituted with an aryl group or an aralkyl group such as a 4-benzylbenzyl group, a 4-phenethylbenzyl group, a 4-phenylbenzyl group; 4-methoxybenzyl group, 4-n-tetradecyloxybenzyl group, 4-n-heptadecyloxybenzyl group, 3,4-dimethoxybenzyl group, 4-methoxymethylbenzyl group, 4-vinyloxymethylbenzyl group, 4
  • An aralkyl group substituted with a substituted oxy group such as a benzyloxybenzyl group or 4-phenethyloxybenzyl group
  • An aralkyl group substituted with a hydroxyl group such as a 4-hydroxybenzyl group and
  • Examples of the substituted or unsubstituted alkoxy group include methoxy group, ethoxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, isobutyloxy group, tert-butyloxy group, sec-butyloxy group, and n-pentyl.
  • Oxy group isopentyloxy group, n-hexyloxy group, 2-methylpentyloxy group, 1,1-dimethylbutyloxy group, 1,2,2-trimethylpropyloxy group, 2-ethylbutyloxy group, 1, 3-dimethylhexyloxy group, cyclohexyloxy group, methylcyclopentyloxy group, n-heptyloxy group, n-heptyloxy group, n-octyloxy group, 3,5,5-trimethylhexyloxy group, n-decyloxy group, n-undecyloxy group, n-dodecyloxy group, 1-a Manchiruokishi group, a straight-chain, such as n- pentadecyl group, branched or cyclic unsubstituted alkoxy group;
  • An alkoxy group substituted with an alkoxycarbonyl group such as a methoxycarbonylmethoxy group, an ethoxycarbonylmethoxy group, an n-propyloxycarbonylmethoxy group, an isopropyloxycarbonylmethoxy group, or a (4′-ethylcyclohexyloxy) carbonylmethoxy group;
  • An alkoxy group substituted with an alkoxycarbonyl group such as a methoxycarbonylethoxy group, an ethoxycarbonylethoxy group, an n-propyloxycarbonylethoxy group, or an ethoxycarbonylpropyloxy group;
  • Methylaminomethoxy group 2-methylaminoethoxy group, 2- (2-methylaminoethoxy) ethoxy group, 4-methylaminobutyloxy group, 1-methylaminopropan-2-yloxy group, 3-methylaminopropyloxy group 2-methylamino-2-methylpropyloxy group, 2-ethylaminoethoxy group, 2- (2-ethylaminoethoxy) ethoxy group, 3-ethylaminopropyloxy group, 1-ethylaminopropyloxy group, 2- An alkoxy group substituted with an alkylamino group such as an isopropylaminoethoxy group, 2- (n-butylamino) ethoxy group, 3- (n-hexylamino) propyloxy group, 4- (cyclohexylamino) butyloxy group; Dimethylaminomethoxy group, 2-dimethylaminoethoxy group, 2- (2-dimethylaminoe
  • Substituted or unsubstituted aryloxy groups include heteroaryloxy groups such as phenyloxy group, 2-methylphenyloxy group, 4-methylphenyloxy group, 4-ethylphenyloxy group, 4-isopropylphenyl group.
  • Examples of the substituted or unsubstituted alkylthio group include a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, an n-butylthio group, an isobutylthio group, a tert-butylthio group, a sec-butylthio group, and an n-pentylthio group.
  • Methylaminomethylthio group 2-methylaminoethylthio group, 2- (2-methylaminoethoxy) ethylthio group, 4-methylaminobutylthio group, 1-methylaminopropan-2-yloxy group, 3-methylaminopropylthio group Group, 2-ethylaminoethylthio group, 2- (2-ethylaminoethoxy) ethylthio group, 3-ethylaminopropylthio group, 1-ethylaminopropylthio group, 2-isopropylaminoethylthio group, 2- (n An alkylthio group substituted with an alkylamino group such as a butylamino) ethylthio group, a 3- (n-hexylamino) propylthio group, or a 4- (cyclohexylamino) butylthio group; Dimethylaminomethylthio group, 2-
  • the substituted or unsubstituted arylthio group also includes a heteroarylthio group, such as a phenylthio group, a 2-methylphenylthio group, a 4-methylphenylthio group, a 3-ethylphenylthio group, a 4-n-propylphenyl group.
  • a heteroarylthio group such as a phenylthio group, a 2-methylphenylthio group, a 4-methylphenylthio group, a 3-ethylphenylthio group, a 4-n-propylphenyl group.
  • substituted or unsubstituted alkylcarbonyl group examples include formyl group, acetyl group, propionyl group, butyryl group, valeryl group, iso-valeryl group, sec-valeryl group, trimethylacetyl group, hexanoyl group, tert-butylacetyl group , Heptanoyl group, octanoyl group, 2-ethylhexanoyl group, nonanoyl group, decanoyl group, undecanoyl group, lauroyl group, tridecanoyl group, tetraadecanoyl group, pentadecanoyl group, hexadecanoyl group, heptadecanoyl group, octadecanoyl group Group, oleoyl group, cyclopentanecarbonyl group, cyclohexanecarbonyl group, 6-chlorohexano
  • Examples of the substituted or unsubstituted arylcarbonyl group include benzoyl group, 2-methylbenzoyl group, 3-methylbenzoyl group, 4-methylbenzoyl group, 4-ethylbenzoyl group, 4-n-propylbenzoyl group, 4- tert-butylbenzoyl group, 2,4-dimethylbenzoyl group, 2,4,6-trimethylbenzoyl group, 2,4,5-trimethylbenzoyl group, 4-ethylbenzoyl group, 4-isopropylbenzoyl group, 4-n- Butylbenzoyl group, 4-isobutylbenzoyl group, 4-sec-butylbenzoyl group, 4-tert-butylbenzoyl group, 4-n-pentylbenzoyl group, 4-isopentylbenzoyl group, 4-neopentibenzoyl group, 4- Isohexyl benzoyl group, 4-cyclohexyl benzo
  • substituted or unsubstituted amino group examples include amino groups such as methylamino group, ethylamino group, propylamino group, butylamino group, pentylamino group, hexylamino group, heptylamino group, octylamino group, 2-ethylhexyl Monoalkylamino groups such as amino group, cyclohexylamino group, 3,5,5-trimethylhexylamino group, nonylamino group, decylamino group; Dimethylamino group, diethylamino group, methylethylamino group, di-n-propylamino group, di-n-butylamino group, di-n-pentylamino group, N-methyl-N-ethylamino group, N-ethyl- Dialkylamino groups such as N-isopropylamino group, N-ethyl-N-
  • R 1 is preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms.
  • R 1 is a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms or a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.
  • R 1 examples of these R 1 are shown below.
  • the substituted or unsubstituted alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and an isopentyl group.
  • a linear, branched or cyclic unsubstituted alkyl group such as 1-methylheptyl group, 2-ethylhexyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group;
  • Alkyloxy or alkenyloxy such as methoxymethyl, ethoxymethyl, n-butoxymethyl, n-hexyloxymethyl, (2-ethylbutyloxy) methyl, 2- (4'-pentenyloxy) ethyl
  • Examples of the substituted or unsubstituted alkenyl group include a vinyl group, a propenyl group, a 1-butenyl group, an isobutenyl group, a 1-pentenyl group, a 2-pentenyl group, a 2-methyl-1-butenyl group, and a 2-cyclopentenyl group.
  • Examples of the substituted or unsubstituted aryl group include phenyl group, 1-naphthyl group, 2-naphthyl group, 2-anthracenyl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 1-pyrenyl group, Unsubstituted aryl groups such as 2-pyrenyl group, 2-perylenyl group, 3-perylenyl group, 2-fluoranthenyl group, 3-fluoranthenyl group, 7-fluoranthenyl group, 8-fluoranthenyl group, etc .: 1-methyl-2-pyrenyl group, 2-methylphenyl group, 4-ethylphenyl group, 4- (4′-tert-butylcyclohexyl) phenyl group, 3-cyclohexylphenyl group, 2-cyclohexylphenyl group, 4-ethyl An aryl group substituted with an alkyl group such as a 1-
  • Examples of the substituted or unsubstituted aralkyl group include benzyl group, ⁇ -methylbenzyl group, phenethyl group, ⁇ -methylphenethyl group, ⁇ , ⁇ -dimethylbenzyl group, ⁇ , ⁇ -dimethylphenethyl group, 4-methylphenethyl group.
  • An aralkyl group unsubstituted or substituted with an alkyl group such as a group, 4-methylbenzyl group, 4-isopropylbenzyl group, etc .
  • Aralkyl groups substituted with aryl groups or aralkyl groups such as 4-benzylbenzyl group, 4-phenethylbenzyl group and 4-phenylbenzyl group: 4-methoxybenzyl group, 4-n-tetradecyloxybenzyl group, 4-n-heptadecyloxybenzyl group, 3,4-dimethoxybenzyl group, 4-methoxymethylbenzyl group, 4-vinyloxymethylbenzyl group, 4
  • An aralkyl group substituted by a substituted oxy group such as benzyloxybenzyl group or 4-phenethyloxybenzyl group:
  • Aralkyl groups substituted with hydroxyl groups such as 4-hydroxybenzyl group and 4-hydroxy-3-methoxybenzyl group:
  • R 2 of the imino compound represented by the general formula (2) and R 3 and R 4 of the imino compound represented by the general formula (3) are preferably a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, A substituted or unsubstituted alkyl group having 1 to 8 carbon atoms is more preferable. Specific examples of these R 2 , R 3 and R 4 are shown below.
  • Examples of the substituted or unsubstituted alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and an isopentyl group.
  • Alkyloxy or alkenyl such as methoxymethyl, ethoxymethyl, n-butoxymethyl, n-hexyloxymethyl, (2-ethylbutyloxy) methyl, 2- (4'-pentenyloxy) ethyl
  • Alkyl groups substituted with oxy groups Alkyl groups substituted with aralkyloxy groups such as benzyloxymethyl group and 2- (benzyloxymethoxy) ethyl group: Alkyl groups substituted with aryloxy groups such as
  • R 3 and R 4 of the imino compound represented by the general formula (3) are bonded to form a ring.
  • the ring formed by combining R 3 and R 4 includes a substituted or unsubstituted dioxolane ring, substituted or unsubstituted, formed together with the oxygen atom substituted by R 3 and R 4 and their common basic carbon atom.
  • the dioxane ring is preferred.
  • the substituent is the same as the substituent that R 2 , R 3 and R 4 have when they are substituted alkyl groups.
  • ring in which R 3 and R 4 are bonded include, for example, ethane-1,2-diyl ring, propane-1,3-diyl ring, butane-1,4-diyl ring, pentane-1,5-diyl Ring, hexane-1,6-diyl ring, 1-methylethane-1,2-diyl ring, 1-n-butylethane-1,2-diyl ring, 2-ethylpropane-1,3-diyl ring, 1-methyl -Propane-1,3-diyl ring, 1-n-butyl-propane-1,3-diyl ring, 2-n-butyl-butane-1,4-diyl ring, 2,4-dimethyl-butane-1, 4-diyl ring, 3-isopentyl-pentane-1,5-diyl ring, 2,3,4-trimethylpentane
  • component I represented by the general formula (1), (2) or (3) are shown in the following Table 1, but the present invention is not limited thereto.
  • Component I represented by the general formula (1), (2) or (3) is known in JP-A-8-113561, JP-A-8-199081, JP-A-8-225753, etc. It can be produced with reference to the method.
  • the compound of the specific example (3) -1 can be obtained by stirring 1,1-dimethoxy-3-iminoisone indoline and p-toluic acid in acetone for 30 minutes and filtering the precipitate.
  • Component P used in the present invention is a pyrrolinone compound represented by the general formula (4).
  • A represents a substituted or unsubstituted aromatic ring, a substituted or unsubstituted heterocyclic ring
  • R 5 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group.
  • A is preferably a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted quinoline ring.
  • Substituted or unsubstituted pyrrole ring, substituted or unsubstituted indole ring, substituted or unsubstituted thiophene ring, substituted or unsubstituted benzothiophene ring, substituted or unsubstituted furan ring, substituted or unsubstituted benzofuran ring is there.
  • A is more preferably a substituted or unsubstituted benzene ring, a substituted or unsubstituted pyridine ring, a substituted or unsubstituted pyrrole ring, a substituted or unsubstituted thiophene ring, a substituted or unsubstituted benzothiophene ring, substituted or An unsubstituted benzofuran ring.
  • Examples of the substituent when A has a substituent include a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted group
  • An alkoxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted amino group, a substituted or unsubstituted heterocyclic group, a cyano group, a halogen atom and the like are preferable.
  • it is a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 25 carbon atoms, or 2 to 2 carbon atoms.
  • it is a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 15 carbon atoms, or 2 to 2 carbon atoms.
  • Examples of the substituted or unsubstituted alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and an isopentyl group.
  • Alkyloxy or alkenyl such as methoxymethyl, ethoxymethyl, n-butoxymethyl, n-hexyloxymethyl, (2-ethylbutyloxy) methyl, 2- (4'-pentenyloxy) ethyl
  • Alkyl groups substituted with oxy groups Alkyl groups substituted with an aralkyloxy group such as benzyloxymethyl group and 2- (benzyloxymethoxy) ethyl group, phenyloxymethyl group, 4-chlorophen
  • Examples of the substituted or unsubstituted aryl group include phenyl group, 1-naphthyl group, 2-naphthyl group, 2-anthracenyl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 1-pyrenyl group, Unsubstituted aryl groups such as 2-pyrenyl group, 2-perylenyl group, 3-perylenyl group, 2-fluoranthenyl group, 3-fluoranthenyl group, 7-fluoranthenyl group, 8-fluoranthenyl group, etc .: 1-methyl-2-pyrenyl group, 2-methylphenyl group, 4-ethylphenyl group, 4- (4′-tert-butylcyclohexyl) phenyl group, 3-cyclohexylphenyl group, 2-cyclohexylphenyl group, 4-ethyl An aryl group substituted with an alkyl group such as a 1-
  • Examples of the substituted or unsubstituted aralkyl group include benzyl group, ⁇ -methylbenzyl group, phenethyl group, ⁇ -methylphenethyl group, ⁇ , ⁇ -dimethylbenzyl group, ⁇ , ⁇ -dimethylphenethyl group, 4-methylphenethyl group.
  • An aralkyl group unsubstituted or substituted with an alkyl group such as a group, 4-methylbenzyl group, 4-isopropylbenzyl group, etc .
  • Aralkyl groups substituted with aryl groups or aralkyl groups such as 4-benzylbenzyl group, 4-phenethylbenzyl group and 4-phenylbenzyl group: 4-methoxybenzyl group, 4-n-tetradecyloxybenzyl group, 4-n-heptadecyloxybenzyl group, 3,4-dimethoxybenzyl group, 4-methoxymethylbenzyl group, 4-vinyloxymethylbenzyl group, 4
  • An aralkyl group substituted by a substituted oxy group such as benzyloxybenzyl group or 4-phenethyloxybenzyl group: Aralkyl groups substituted with hydroxyl groups such as 4-hydroxybenzyl group and 4-hydroxy-3-methoxybenzyl group: Aralky
  • Examples of the substituted or unsubstituted alkenyl group include a vinyl group, a propenyl group, a 1-butenyl group, an isobutenyl group, a 1-pentenyl group, a 2-pentenyl group, a 2-methyl-1-butenyl group, and a 2-cyclopentenyl group.
  • Examples of the substituted or unsubstituted alkoxy group include methoxy group, ethoxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, isobutyloxy group, tert-butyloxy group, sec-butyloxy group, and n-pentyl.
  • Oxy group isopentyloxy group, n-hexyloxy group, 2-methylpentyloxy group, 1,1-dimethylbutyloxy group, 1,2,2-trimethylpropyloxy group, 2-ethylbutyloxy group, 1, 3-dimethylhexyloxy group, cyclohexyloxy group, methylcyclopentyloxy group, n-heptyloxy group, n-heptyloxy group, n-octyloxy group, 3,5,5-trimethylhexyloxy group, n-decyloxy group, n-undecyloxy group, n-dodecyloxy group, 1-a Manchiruokishi group, a straight-chain, such as n- pentadecyloxy group, branched or cyclic unsubstituted alkoxy group:
  • Alkoxy groups substituted with alkoxycarbonyl groups such as methoxycarbonylmethoxy group, ethoxycarbonylmethoxy group, n-propyloxycarbonylmethoxy group, isopropyloxycarbonylmethoxy group, (4'-ethylcyclohexyloxy) carbonylmethoxy group, methoxycarbonylethoxy
  • An alkoxy group substituted by an alkoxycarbonyl group such as a group, ethoxycarbonylethoxy group, n-propyloxycarbonylethoxy group, ethoxycarbonylpropyloxy group;
  • Methylaminomethoxy group 2-methylaminoethoxy group, 2- (2-methylaminoethoxy) ethoxy group, 4-methylaminobutyloxy group, 1-methylaminopropan-2-yloxy group, 3-methylaminopropyloxy group 2-methylamino-2-methylpropyloxy group, 2-ethylaminoethoxy group, 2- (2-ethylaminoethoxy) ethoxy group, 3-ethylaminopropyloxy group, 1-ethylaminopropyloxy group, 2- An alkoxy group substituted with an alkylamino group such as an isopropylaminoethoxy group, 2- (n-butylamino) ethoxy group, 3- (n-hexylamino) propyloxy group, 4- (cyclohexylamino) butyloxy group; Dimethylaminomethoxy group, 2-dimethylaminoethoxy group, 2- (2-dimethylaminoe
  • Alkoxy substituted with alkylaminoalkoxy groups such as methylaminomethoxymethoxy group, methylaminoethoxyethoxy group, methylaminoethoxypropyloxy group, ethylaminoethoxypropyloxy group, 4- (2'-isobutylaminopropyloxy) butyloxy group Group; Alkoxy groups substituted with dialkylaminoalkoxy groups such as dimethylaminomethoxymethoxy group, dimethylaminoethoxyethoxy group, dimethylaminoethoxypropyloxy group, diethylaminoethoxypropyloxy group, 4- (2'-diisobutylaminopropyloxy) butyloxy group ; Methylthiomethoxy group, 2-methylthioethoxy group, 2-ethylthioethoxy group, 2-n-propylthioethoxy group, 2-isopropylthioethoxy group, 2-n-buty
  • Examples of the substituted or unsubstituted alkylthio group include a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, an n-butylthio group, an isobutylthio group, a tert-butylthio group, a sec-butylthio group, and an n-pentylthio group.
  • Methylaminomethylthio group 2-methylaminoethylthio group, 2- (2-methylaminoethoxy) ethylthio group, 4-methylaminobutylthio group, 1-methylaminopropan-2-yloxy group, 3-methylaminopropylthio group Group, 2-ethylaminoethylthio group, 2- (2-ethylaminoethoxy) ethylthio group, 3-ethylaminopropylthio group, 1-ethylaminopropylthio group, 2-isopropylaminoethylthio group, 2- (n An alkylthio group substituted with an alkylamino group such as a butylamino) ethylthio group, a 3- (n-hexylamino) propylthio group, or a 4- (cyclohexylamino) butylthio group; Dimethylaminomethylthio group, 2-
  • Methylthiomethylthio group 2-methylthioethylthio group, 2-ethylthioethylthio group, 2-n-propylthioethylthio group, 2-isopropylthioethylthio group, 2-n-butylthioethylthio group, 2-isobutyl
  • An alkylthio group substituted with an alkylthio group such as a thioethylthio group or a (3,5,5-trimethylhexylthio) hexylthio group; 2-N-morpholinylethylthio group, 2-N-pyridylethylthio group, 2-N-pyrrolylethylthio group, 2- (2-furyl) ethylthio group, 2- (1-indolyl) ethylthio group, 2- (3-thienyl) ethylthio group, 3-N-morpholinylpropyl
  • substituted or unsubstituted amino group examples include amino groups such as methylamino group, ethylamino group, propylamino group, butylamino group, pentylamino group, hexylamino group, heptylamino group, octylamino group, 2-ethylhexyl Monoalkylamino groups such as amino group, cyclohexylamino group, 3,5,5-trimethylhexylamino group, nonylamino group, decylamino group;
  • Aryl group such as amino group, N-methyl-N- (3-chlorophenyl) amino group, diphenylamino group, di- (p-tolyl) amino group,
  • R 5 is preferably a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted group having 6 to 24 carbon atoms.
  • R 5 is a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, carbon A substituted or unsubstituted aralkyl group of formulas 7 to 19; More preferably, R 5 is a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 8 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, carbon A substituted or unsubstituted aralkyl group of formulas 7 to 13;
  • R 5 examples of the substituted or unsubstituted alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and an isopentyl group.
  • Alkyloxy or alkenyloxy such as methoxymethyl, ethoxymethyl, n-butoxymethyl, n-hexyloxymethyl, (2-ethylbutyloxy) methyl, 2- (4'-pentenyloxy) ethyl
  • Examples of the substituted or unsubstituted alkenyl group include a vinyl group, a propenyl group, a 1-butenyl group, an isobutenyl group, a 1-pentenyl group, a 2-pentenyl group, a 2-methyl-1-butenyl group, and a 2-cyclopentenyl group.
  • Examples of the substituted or unsubstituted aryl group include phenyl group, 1-naphthyl group, 2-naphthyl group, 2-anthracenyl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 1-pyrenyl group, Unsubstituted aryl groups such as 2-pyrenyl group, 2-perylenyl group, 3-perylenyl group, 2-fluoranthenyl group, 3-fluoranthenyl group, 7-fluoranthenyl group, 8-fluoranthenyl group, etc .: 1-methyl-2-pyrenyl group, 2-methylphenyl group, 4-ethylphenyl group, 4- (4'-tert-butylcyclohexyl) phenyl group, 3-cyclohexylphenyl group, 2-cyclohexylphenyl group, 4-ethyl An aryl group substituted with an alkyl group such as a 1-
  • Examples of the substituted or unsubstituted aralkyl group include benzyl group, ⁇ -methylbenzyl group, phenethyl group, ⁇ -methylphenethyl group, ⁇ , ⁇ -dimethylbenzyl group, ⁇ , ⁇ -dimethylphenethyl group, 4-methylphenethyl group.
  • An aralkyl group unsubstituted or substituted with an alkyl group such as a group, 4-methylbenzyl group, 4-isopropylbenzyl group, etc .
  • Aralkyl groups substituted with aryl groups or aralkyl groups such as 4-benzylbenzyl group, 4-phenethylbenzyl group and 4-phenylbenzyl group: 4-methoxybenzyl group, 4-n-tetradecyloxybenzyl group, 4-n-heptadecyloxybenzyl group, 3,4-dimethoxybenzyl group, 4-methoxymethylbenzyl group, 4-vinyloxymethylbenzyl group, 4
  • An aralkyl group substituted by a substituted oxy group such as benzyloxybenzyl group or 4-phenethyloxybenzyl group: Aralkyl groups substituted with hydroxyl groups such as 4-hydroxybenzyl group and 4-hydroxy-3-methoxybenzyl group: Aralky
  • the component P represented by the general formula (4) is known in JP-A-61-115056, JP-A-61-115960, JP-A-7-285920, etc., and is prepared by referring to a known method. can do.
  • the compound of the specific example (4) -2 can be produced by heating diethyl 2-benzoylsuccinate and ammonium acetate in acetic acid.
  • thermosensitive coloring composition containing component I and component P of the present invention will be described below.
  • the thermochromic composition of the present invention contains Component I and Component P of the present invention as essential components, but optionally contains other components such as a binder.
  • the type and amount of the other components vary depending on the color developing material to which the thermosensitive coloring composition is applied. It is preferable for application of the thermosensitive coloring composition that component I and component P of the present invention are solid at room temperature. Is not a requirement. Even in the case of a liquid at room temperature, it can be applied by means such as microencapsulation.
  • Component I and Component P can be used alone or in admixture of two or more.
  • the color-forming material include color-forming recording materials such as heat-sensitive recording materials, energized color recording materials, and laser light recording materials, and are used in combination with other recording methods such as magnetic recording, metal thin film recording, and cloudiness recording. It is also possible to do.
  • component I and component P are each ground and dispersed into fine particles, then both are mixed, and if necessary, a binder and other auxiliary agents are added to the thermosensitive color-forming composition of the present invention.
  • a coating liquid containing a product is prepared, and the coating liquid is applied to a support and dried.
  • a color former hereinafter referred to as a component that forms the color former, Component I and Component P are referred to as “color precursors”. Abbreviated
  • the color former can be formed on the entire recording layer, or can be formed only at a desired location. If the heating temperature is lower than 80 ° C., it takes a long time for color development, or if the color density is low and the temperature is higher than 300 ° C., the color precursor tends to be easily decomposed.
  • the thermal energy for forming the color former is not particularly limited, but for example, thermal energy such as a thermal head, hot stamp, and thermal pen may be used, or light energy such as laser light can be obtained by photothermal conversion. Thermal energy may be used. As a result, any energy source that can be converted into thermal energy can be used.
  • the resulting colored body exhibits various hues and exhibits high fastness to light, heat, humidity, plasticizer, oil and the like.
  • a heat-sensitive recording material obtained by selecting paper, film or sheet as a support, and carrying a recording layer containing the heat-sensitive color-forming composition of the present invention on the support, a color image of the heat-sensitive recording material is obtained. Is extremely fast.
  • thermochromic composition of the present invention can also be dissolved or dispersed in a solvent and used as an ink or a paint. If the ink or paint obtained in this way is applied to a part of a food container, such as an aluminum can, a glass bottle, or a rubber packing, the part painted by the heat treatment after filling the food will have a brilliant hue. Since it changes, it can be used to determine whether or not the heat treatment has been completed. Further, by applying heat energy to the heat-sensitive color-forming composition of the present invention, a dark and strong colored body can be obtained, and this colored body can be pulverized to obtain an organic pigment. When a paint is produced using this organic pigment, a strong and robust paint can be obtained.
  • thermosensitive recording material containing the thermosensitive coloring composition of the present invention will be described below.
  • the heat-sensitive recording material is provided with a recording layer containing the heat-sensitive color forming composition of the present invention on a support.
  • the color-forming precursor is uniformly dispersed or dissolved in water or an organic solvent together with a binder resin, or microencapsulated, and this is coated on a support and dried to produce a heat-sensitive coating liquid.
  • the coloring precursor may be dispersed in water or an organic solvent, and a binder may be added.
  • the component I and the component P constituting the color forming precursor may be dispersed together, or may be mixed after being dispersed separately.
  • the recording layer can be formed by applying and drying the heat-sensitive coating liquid thus obtained on a support.
  • the application method is not particularly limited.
  • the heat-sensitive coating liquid may be in a dispersed state in which the color precursor is contained as fine particles, or may be in a completely dissolved solution state.
  • the molar ratio of component I and component P constituting the color precursor is preferably 1: 0.5 to 1: 5, more preferably 1: 1 to 1: 3.
  • the weight ratio of the color former to the binder is preferably 1: 1 to 1: 0.01, more preferably 1: 0.5 to 1: 0.05.
  • the dispersion medium water or an organic solvent (toluene, methanol, ethanol, isopropyl alcohol, n-hexane, cyclohexane, n-octanol, ethylcyclohexane, dioxane, etc.) is used.
  • a binder when the dispersion medium is water polyvinyl alcohol resin, methyl cellulose resin, hydroxyethyl cellulose resin, carboxymethyl cellulose resin, methyl vinyl ether / maleic anhydride copolymer resin, polyacrylic acid resin, polyvinyl pyrrolidone resin, acrylic amide resin, Gelatin, gum arabic, etc. can be used.
  • the binder when the dispersion medium is an organic solvent, alkyd resin, vinyl chloride resin, urethane resin, xylene resin, phenol resin, coumarone resin, vinyl toluene resin, terpene resin, vinyl toluene / butadiene copolymer resin, vinyl toluene / An acrylate copolymer resin, a styrene / acrylate copolymer resin, a vinyl / isobutyl ether copolymer resin, or the like can be used.
  • a light absorber In the recording layer, a light absorber, a melting point depressant, an ultraviolet absorber, an antioxidant, organic and inorganic pigments and the like can be added according to the purpose.
  • the light absorber is not limited as long as it can absorb light in the wavelength region of the laser beam and convert it into thermal energy.
  • Melting point depressants include waxes such as paraffin wax, polyethylene wax, higher fatty acids and esters thereof, acid amides such as stearamide, diphenyls such as 4,4′-dimethylbiphenyl, and methylolamide.
  • Naphthalenes such as 1,3-dinitronaphthalene, ureas, acids such as phthalic anhydride, acetanilide, benzanilide, anilides such as alkylcarboxylic acid anilide, triphenyls, phthalonitriles, bisresorcinol ethylene Ethers such as ether, salicylic acid derivatives such as 4-t-butyl salicylate, ethyl-2-cyano-3,3-diphenyl acrylate, benzotriazoles, fluorene, dimethyl isophthalate, diphenyl sulfone, mandelic acid, Benzoin, Such as ethyl anthraquinone, coumarone compounds, carbazoles such as N-ethylcarbazole, sulfonamides, triphenylmethanes, thiazoles such as dibenzothiazyl disulfide, N-cyclohexyl-2-benzo
  • ultraviolet absorbers examples include benzotriazole and derivatives thereof, benzoin and derivatives thereof, 2-chloroanthraquinone, benzol peroxide, salicylic acid esters such as pt-butylphenyl salicylate, and cyanoacrylates such as ethyl diphenylacrylate. And the like.
  • Antioxidants include 2,6-di-t-butyl-4-methylphenol, di (3-t-butyl-4-hydroxy-5-methylphenyl) thioether, 1,1-bis (2-methyl- Hindered phenols such as 4-hydroxy-5-t-butylphenyl) butane and hindered amines such as di (2,2,6,6-tetramethyl-4-piperidine) sebacate.
  • the pigment include talc, clay, silica, calcined kaolin, zinc oxide, silicon oxide, titanium oxide, aluminum hydroxide, calcium carbonate, magnesium carbonate, and urea-formalin resin.
  • a protective layer can be provided on the recording layer, and an undercoat layer can be provided below the recording layer.
  • urethane resin, polyolefin resin, polyester resin, vinyl resin, epoxy resin, and acrylic resin can be used.
  • the undercoat layer heat-insulating fine hollow particles, calcined kaolin, organic pigments, thermally expandable microcapsules and the like can be used in order to improve color developability.
  • paper, synthetic paper, film, sheet, laminated paper, nonwoven fabric sheet or the like can be used according to the purpose.
  • the film or sheet examples include polyesters such as polyethylene terephthalate and polybutylene terephthalate, cellulose derivatives such as cellulose triacetate, polyolefins such as polypropylene and polyethylene, and plastic films or sheets such as polyethylene naphthalate and polystyrene. Only one of these plastic films or sheets may be used, or a laminate of them may be used. In addition, when a plurality of sheets are stacked and a card is obtained with a punching machine after heat-sealing between the sheets with a vacuum press machine, any one of the sheets serves as a support.
  • polyesters such as polyethylene terephthalate and polybutylene terephthalate
  • cellulose derivatives such as cellulose triacetate
  • polyolefins such as polypropylene and polyethylene
  • plastic films or sheets such as polyethylene naphthalate and polystyrene. Only one of these plastic films or sheets may be used, or a laminate of them may be used.
  • the support may be transparent, opaque, or translucent depending on the application, but the support is substantially used for the production of the transparent heat-sensitive recording material. It is preferably transparent. Specifically, a plastic film or sheet having a Haze value of 10% or less is preferably used, and a polyethylene terephthalate film or sheet is most preferable from the viewpoints of cost, heat resistance of the support, and the like. Moreover, the said plastic film or sheet
  • seat may be colored by arbitrary hues according to the objective. For example, in the case of a medical image diagnostic film used for shaukasten, it may be colored blue.
  • thermosensitive coloring composition of the present invention has a high transparency when dissolved or dispersed in a solvent and has almost no coloration, but has a clear and high color density when colored by heating, and has a very high fastness. Form. Therefore, it is very suitable for a transparent thermosensitive recording material.
  • Synthesis Example 5 Synthesis of Component P (Specific Example Compound (4) -2) 139.1 g of diethyl 2-benzoylsuccinate and 102.1 g of ammonium acetate were added to 300 mL of acetic acid and stirred at 100 to 105 ° C. for 24 hours. After cooling, the reaction mixture was drained into 500 mL of water. The precipitate was collected by filtration, and the filter paste was dispersed and washed with 500 mL of methanol and dried to obtain 52 g of Compound No. (4) -2 of the pyrrolino compound shown in Table 2 as a white powder. Melting point: 180-181 ° C The obtained compound was confirmed to be the target compound from the following analysis results.
  • thermosensitive recording material As component I, 4.2 g of the compound synthesized in Synthesis Example 4 and 5.7 g of the compound synthesized in Synthesis Example 5 as Component P were each mixed with 30 mL of toluene in a sand mill. Time grinding was performed to obtain a dispersion. Next, the dispersion liquid of component I and the dispersion liquid of component P were combined, and 100 g of “Almatex” (trade name: manufactured by Mitsui Chemicals) as a binder was added and mixed well to prepare a thermosensitive coloring composition. This thermosensitive color-developing composition was applied and dried on fine paper so that the dry coating amount was 6 g / m 2 to obtain a thermosensitive recording material.
  • Almatex trade name: manufactured by Mitsui Chemicals
  • the obtained heat-sensitive recording material was brought into contact with an iron at 200 ° C. for 3 seconds to obtain a full color image. This color image was bright blue.
  • the color images of the heat-sensitive recording material obtained above were measured and evaluated for the following items. The evaluation results are shown in Table 4.
  • Example 2 Production of thermosensitive recording material
  • Example 1 5.9 g of the same compound as component I instead of 4.2 g of the compound synthesized in Synthesis Example 4 and Component P as the component P in Example 1 were synthesized.
  • a heat-sensitive recording material and a full color image were obtained in the same manner as in Example 1 except that 4.0 g of the same compound was used instead of 5.8 g of the compound. This color image was bright yellow.
  • the same evaluation test as in Example 1 was performed on this color image. The results are shown in Table 4.
  • Example 3 Production of Thermosensitive Recording Material
  • Component I instead of Compound 4.2 g synthesized in Synthesis Example 4, Compound 4.3 g synthesized in Synthesis Example 1 and Component P as a synthesis example
  • a heat-sensitive recording material and a full-color image were obtained in the same manner as in Example 1 except that 5.6 g of the same compound was used instead of 5.7 g of the compound synthesized in 5.
  • This color image was bright blue-purple.
  • the same evaluation test as in Example 1 was performed on this color image. The results are shown in Table 4.
  • Example 4 to 23 Preparation of heat-sensitive recording material The same operations as in Example 1 were carried out using the compounds listed in Table 3 for component I and component P in Example 1, respectively. I got a statue. The same evaluation test as in Example 1 was performed on the obtained color image. The results are shown in Table 4.
  • Example 24 Preparation of heat-sensitive recording material
  • component I 4.2 g of the compound synthesized in Synthesis Example 4 and 5.7 g of the compound synthesized in Synthesis Example 5 as Component P were each used as a binder in a 5% aqueous polyvinyl alcohol solution.
  • the mixture was ground with a sand mill for 2 hours to obtain a dispersion.
  • the component I dispersion and the component P dispersion were combined, and 5 parts of a 60% light calcium carbonate aqueous dispersion was added and mixed well to prepare a thermosensitive coloring composition.
  • thermosensitive color-developing composition was applied and dried on fine paper so that the dry coating amount was 6 g / m 2 to obtain a thermosensitive recording material.
  • This heat-sensitive recording material was subjected to the same operation as in Example 1 to form a colored body, and the same evaluation test as in Example 1 was performed on this color image. The results are shown in Table 4.
  • thermosensitive coloring composition Production of transparent thermosensitive recording material
  • This thermosensitive coloring composition was applied and dried on a colorless and transparent polyethylene terephthalate film having a thickness of 180 ⁇ m so that the dry coating amount was 6 g / m 2 to obtain a heat-sensitive recording material having high transparency.
  • the transparent thermosensitive recording material was subjected to the same operation as in Example 1 to form a colored body, and the same evaluation test as in Example 1 was performed on this color image. The results are shown in Table 4.
  • thermosensitive recording material in Example 1, instead of the compound synthesized in Synthesis Example 4 as Component I, 5 g of 2-anilino-3-methyl-6-di-n-butylaminofluorane, As component P, the same operation as in Example 1 was carried out except that 5 g of bisphenol A was used instead of the compound synthesized in Synthesis Example 5 to obtain a heat-sensitive recording material and a full color image. This colored image was black. The same evaluation test as in Example 1 was performed on this color image. The results are shown in Table 4.
  • the heat-sensitive recording material using the heat-sensitive color forming composition of the present invention is very useful because it is particularly excellent in fastness of the color image.
  • thermosensitive color-forming composition that forms a colored body having a clear and high color density and extremely high fastness, and a heat-sensitive recording material using the composition. Further, it has become possible to provide a transparent thermosensitive recording material having high transparency, high color density, and excellent image storability.

Abstract

La présente invention permet de fournir : une composition de développement de couleur thermosensible pour former un corps de développement de couleur du jaune au bleu très résistant ayant une densité de couleur puissante et élevée ; et un matériau de publication thermosensible contenant la composition de développement de couleur thermosensible. La présente invention concerne une composition de développement de couleur thermosensible contenant un composé d'imino représenté par une formule structurelle spécifique et un composé de pyrrolinone représenté par la formule générale (4), ainsi qu'un matériau de publication thermosensible obtenu par inclusion de ladite composition dans une couche de publication. (Dans la formule, A représente un anneau aromatique substitué ou non substitué ou un anneau hétérocyclique substitué ou non substitué ; et R5 représente un groupe alkyle substitué ou non substitué, un groupe alcényle substitué ou non substitué, un groupe aryle substitué ou non substitué ou un groupe aralkyle substitué ou non substitué.)
PCT/JP2014/062133 2013-05-07 2014-05-02 Composition de développement de couleur thermosensible et matériau de publication thermosensible l'utilisant WO2014181763A1 (fr)

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