Coloring compound and thermal transfer recording sheet

Patent metadata

Field	Value
Publication number	US-11958978-B2
Application number	US-202016879035-A
Country	US
Kind code	B2
Filing date	May 20, 2020
Priority date	Nov 29, 2017
Publication date	Apr 16, 2024
Grant date	Apr 16, 2024

Abstract

A coloring compound comprises a triphenylmethane structure having specific substituents.

First claim

What is claimed is:

1. A coloring compound comprising a structure represented by formula (1-1) or formula (1-2):

where:
R 1 and R 2 each independently represents an unsubstituted alkyl group;
R 3 and R 4 each independently represents a hydrogen atom or an unsubstituted alkyl group;
R 5 and R 6 each independently represents a hydrogen atom or an unsubstituted alkyl group having 1 to 4 carbon atoms;
R 7 and R 8 each independently represents 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 salt group, a benzenesulfonyl group, a trifluoromethylsulfonyl group, or a perfluoroalkyl 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 salt group, a benzenesulfonyl group, a trifluoromethylsulfonyl group, or a perfluoroalkyl group; and
X − represents an anion,
wherein in R 1 to R 4 , the unsubstituted alkyl group is an n-butyl group, a 2-ethylhexyl group, or an octyl group;

where:
R 1 and R 2 each independently represents an unsubstituted alkyl group;
R 3 and R 4 each independently represents a hydrogen atom or an unsubstituted alkyl group;
R 5 and R 6 each independently represents 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 —SO 3 − ; and
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 salt group, a benzenesulfonyl group, a trifluoromethylsulfonyl group, or a perfluoroalkyl group,
wherein in R 1 to R 4 , the unsubstituted alkyl group is an n-butyl group, a 2-ethylhexyl group, or an octyl group.

2. The coloring compound according to claim 1 , wherein R 1 and R 2 in the formula (1-1) and the formula (1-2) represent identical alkyl groups.

3. The coloring compound according to claim 1 , comprising the structure represented by the formula (1-2), which has a moiety B constituted by R 9′ , R 10′ , and a benzene ring to which R 9′ and R 10′ bond,
wherein the moiety B has a structure represented by formula (7):

4. A thermal transfer recording sheet comprising a substrate and a coloring material layer on the substrate,
wherein the coloring material layer comprises a yellow dye layer including a yellow dye, a magenta dye layer including a magenta dye, and a cyan dye layer including a cyan dye, and
wherein the cyan dye includes a coloring compound including a structure represented by formula (1-2) or formula (1-2):

where:
R 1 and R 2 each independently represents an unsubstituted alkyl group;
R 3 and R 4 each independently represents a hydrogen atom or an unsubstituted alkyl group;
R 5 and R 6 each independently represents a hydrogen atom or an unsubstituted alkyl group having 1 to 4 carbon atoms;
R 7 and R 8 each independently represents 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 salt group, a benzenesulfonyl group, a trifluoromethylsulfonyl group, or a perfluoroalkyl 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 salt group, a benzenesulfonyl group, a trifluoromethylsulfonyl group, or a perfluoroalkyl group; and
X − represents an anion,
wherein in R 1 to R 4 , the unsubstituted alkyl group is an n-butyl group, a 2-ethylhexyl group, or an octyl group;

where:
R 1 and R 2 each independently represents an unsubstituted alkyl group;
R 3 and R 4 each independently represents a hydrogen atom or atom, an unsubstituted alkyl group;
R 5 and R 6 each independently represents 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 —SO 3 − ; and
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 salt group, a benzenesulfonyl group, a trifluoromethylsulfonyl group, or a perfluoroalkyl group,
wherein in R 1 to R 4 , the unsubstituted alkyl group is an n-butyl group, a 2-ethylhexyl group, or an octyl group.

5. The thermal transfer recording sheet according to claim 4 , wherein the cyan dye further includes at least one compound selected from the group consisting of compounds represented by formulae (2) and (3):

where R 11 to R 15 each independently represents an alkyl group, an aryl group having a substituent, or an unsubstituted aryl group; and

where R 16 and R 17 each independently represents an alkyl group, an aryl group having a substituent, or an unsubstituted aryl group.

6. The coloring compound according to claim 1 , comprising the structure represented by the formula (1-1), which has a moiety A constituted by R 9 , R 10 , and a benzene ring to which R 9 and R 10 bond,
wherein the moiety A has a structure selected from the group consisting of structures represented by formulae (4) and (5):

7. The thermal transfer recording sheet according to claim 4 , comprising the structure represented by formula (1-1), which has a moiety A constituted by R 9 , R 10 , and a benzene ring to which R 9 and R 10 bond,
wherein the moiety A has a structure selected from the group consisting of structures represented by formulae (4) and (5):

8. The coloring compound according to claim 1 , comprising the structure represented by formula (1-1), which has a moiety A constituted by R 9 , R 10 , and a benzene ring to which R 9 and R 10 bond,
wherein the moiety A has a structure selected from the group consisting of structures represented by formulae (4) to (6):

Assignees

• Canon Kk
• Canon Kabuskiki Kaisha

Inventors

• Hayakawa Ai
• Seki Masanori
• Shirota Koromo
• Muta Hajime
• Shintou Taichi
• Santo Tsuyoshi

Classifications

• C09B55/009 Primary

  Azomethine dyes, the C-atom of the group -C=N- being part of a ring (Image) · CPC title

• B41M5/3858

  Mixtures of dyes, at least one being a dye classifiable in one of groups B41M5/385 - B41M5/39 · CPC title

• C09B1/201

  Dyes with no other substituents than the amino groups · CPC title

• C09B11/12 Primary

  without any OH group bound to an aryl nucleus · CPC title

• C09B57/008

  Triarylamine dyes containing no other chromophores · CPC title