Thermal transfer ink, thermal transfer sheet, and thermal transfer recording method using the same
View Patent ↗Provided are a thermal transfer yellow ink and a thermal transfer sheet capable of providing a thermal transfer recorded product exhibiting a clear yellow tone with a high density by low energy and having an excellent color tone and light resistance, and also capable of exhibiting a favorable green color tone with a high density when mixed with cyan. Provided are a dye composition characterized by comprising a dye having an arylidene pyrazolone skeleton and a dye having a bispyrazolone methine skeleton; a thermal transfer ink characterized by comprising a dye having an arylidene pyrazolone skeleton, a dye having a bispyrazolone methine skeleton, and a medium; and a thermal transfer sheet comprising a substrate and a colorant layer formed thereon, wherein the colorant layer comprises a dye having an arylidene pyrazolone skeleton and a dye having a bispyrazolone methine skeleton.
1. A thermal transfer ink, comprising:
(1) an arylidene pyrazolone dye represented by the following formula (I):
wherein ring A is a benzene ring which optionally has an substituent,
each of R 1 and R 2 which are independent of each other, is a hydrogen atom, an alkyl group which optionally is substituted, an allyl group, an aryl group which optionally is substituted, or a cycloalkyl group which optionally is substituted,
R 3 is a hydrogen atom, an alkyl group which optionally is substituted, an NR 9 R 10 group, an alkoxy group which optionally is substituted, an alkoxycarbonyl group which optionally is substituted, an aryl group which optionally is substituted, or a C(O)NR 9A R 10A group,
R 4 is an alkyl group which optionally is substituted, or an aryl group which optionally is substituted, and
each of R 9 , R 10 , R 9A and R 10A which are independent of one another, is a hydrogen atom, an alkyl group which optionally is substituted, or an aryl group which optionally is substituted;
(2) a bispyrazolone methine dye represented by the following formula (II):
wherein each of R 5 and R 6 which are independent of each other, is an alkyl group which optionally is substituted, an alkenyl group which optionally is substituted, or an aryl group which optionally is substituted,
each of R 7 and R 8 which are independent of each other, is an alkyl group which optionally is substituted, an NR 9B R 10B group, an alkoxy group which optionally is substituted, an alkoxycarbonyl group which may be substituted, an aryl group which optionally is substituted, or a C(O)NR 9C R 10C group, and
each of R 9B , R 10B , R 9C and R 10C which are independent of one another, is a hydrogen atom, an alkyl group which optionally is substituted, or an aryl group which optionally is substituted; and
(3) a medium.
2. The thermal transfer ink according to claim 1 , wherein in the arylidene pyrazolone dye represented by the formula (I), ring A is a benzene ring which optionally is substituted by a substituent selected from the group consisting of a C 1-10 alkyl group which optionally is substituted, a C 1-10 alkoxy group which optionally is substituted, and a halogen atom,
each of R 1 and R 2 which are independent of each other, is a C 1-12 alkyl group which optionally is substituted, an allyl group, a C 6-10 aryl group which optionally is substituted, or a C 5-7 cycloalkyl group which optionally is substituted,
R 3 is a hydrogen atom, a C 1-10 alkyl group which optionally is substituted, a C 1-8 NR 9 R 10 group, a C 1-8 alkoxy group which optionally is substituted, a C 2-9 alkoxycarbonyl group which optionally is substituted, a C 6-10 aryl group which optionally is substituted, or a C 3-9 C(O)NR 9A R 10A group, and
R 4 is a C 1-12 alkyl group which optionally is substituted, or a C 6-10 aryl group which optionally is substituted.
3. The thermal transfer ink according to claim 1 , wherein in the bispyrazolone methine dye represented by the formula (II), each of R 5 and R 6 which are independent of each other, is a C 1-10 alkyl group which optionally is substituted, a C 1-10 alkenyl group which optionally is substituted, or a C 6-10 aryl group which optionally is substituted, and
each of R 7 and R 8 which are independent of each other, is a C 1-10 alkyl group which optionally is substituted, a C 1-8 NR 9B R 10B group, a C 1-8 alkoxy group which optionally is substituted, a C 2-9 alkoxycarbonyl group which optionally is substituted, a C 6-10 aryl group which optionally is substituted, or a C 3-9 C(O)NR 9C R 10C group.
4. A thermal transfer recording sheet, comprising:
a substrate and a colorant layer formed thereon, wherein the colorant layer comprises an arylidene pyrazolone dye represented by the following formula (I):
wherein ring A is a benzene ring which optionally has a substituent,
each of R 1 and R 2 which are independent of each other, is a hydrogen atom, an alkyl group which optionally is substituted, an allyl group, an aryl group which optionally is substituted, or a cycloalkyl group which optionally is substituted,
R 3 is a hydrogen atom, an alkyl group which optionally is substituted, an NR 9 R 10 group, an alkoxy group which optionally is substituted, an alkoxycarbonyl group which optionally is substituted, an aryl group which optionally is substituted, or a C(O)NR 9A R 10A group,
R 4 is an alkyl group which optionally is substituted, or an aryl group which optionally is substituted, and
each of R 9 , R 10 , R 9A and R 10A which are independent of one another, is a hydrogen atom, an alkyl group which optionally is substituted, or an aryl group which optionally is substituted; and
(2) a bispyrazolone methine dye represented by the following formula (II):
wherein each of R 5 and R 6 which are independent of each other, is an alkyl group which optionally is substituted, an alkenyl group which optionally is substituted, or an aryl group which optionally is substituted,
each of R 7 and R 8 which are independent of each other, is an alkyl group which optionally is substituted, an NR 9B R 10B group, an alkoxy group which optionally is substituted, an alkoxycarbonyl group which optionally is substituted, an aryl group which optionally is substituted, or a C(O)NR 9C R 10C group, and
each of R 9B , R 10B , R 9C and R 10C which are independent of one another, is a hydrogen atom, an alkyl group which optionally is substituted, or an aryl group which optionally is substituted.
5. The thermal transfer recording sheet according to claim 4 , wherein in the arylidene pyrazolone dye represented by the formula (I),
the ring A is a benzene ring which optionally is substituted by a substituent selected from the group consisting of a C 1-10 alkyl group which optionally is substituted, a C 1-10 alkoxy group which optionally is substituted, and a halogen atom,
each of R 1 and R 2 which are independent of each other, is a C 1-12 alkyl group which optionally is substituted, an allyl group, a C 6-10 aryl group which optionally is substituted, or a C 5-7 cycloalkyl group which optionally is substituted,
R 3 is a hydrogen atom, a C 1-10 alkyl group which optionally is substituted, a C 1-8 NR 9 R 10 group, a C 1-8 alkoxy group which optionally is substituted, a C 2-9 alkoxycarbonyl group which optionally is substituted, a C 6-10 aryl group which optionally is substituted, or a C 3-9 C(O)NR 9A R 10A group, and
R 4 is a C 1-12 alkyl group which optionally is substituted, or a C 6-10 aryl group which optionally is substituted.
6. The thermal transfer recording sheet according claim 4 , wherein in the bispyrazolone methine dye represented by the formula (II),
each of R 5 and R 6 which are independent of each other, is a C 1-10 alkyl group which optionally is substituted, a C 1-10 alkenyl group which optionally is substituted, or a C 6-10 aryl group which optionally is substituted, and
each of R 7 and R 8 , which are independent of each other, is a C 1-10 alkyl group which optionally is substituted, a C 1-8 NR 9B R 10B group, alkoxy group which optionally is substituted, a C 2-9 alkoxycarbonyl group which optionally is substituted, a C 6-10 aryl group which optionally is substituted, or a C 3-9 C(O)NR 9C R 10C group.
7. A thermal transfer recording method, which comprises:
conducting thermal transfer recording with the thermal transfer recording sheet as defined in claim 4 , wherein a recorded image has a value a* of at least −13 and at most 10 and a value b* of at least 60 in a CIELAB space at a color density of 1.0, in setting at a view angle of 2° and with a D50 light source.