Photoresponsive low-molecular weight material, adhesive, toner, and image forming method

Patent metadata

Field	Value
Publication number	US-2020264530-A1
Application number	US-202016788518-A
Country	US
Kind code	A1
Filing date	Feb 12, 2020
Priority date	Feb 14, 2019
Publication date	Aug 20, 2020
Grant date	—

Abstract

Disclosed is a compound containing a specific structure having an azomethine part, the compound being reversibly fluidized and non-fluidized by being irradiated with light.

First claim

What is claimed is:

1 . A compound represented by a following Chemical Formula 1, the compound being reversibly fluidized and non-fluidized by being irradiated with light:

wherein in the Chemical Formula 1,
X represents NR 10 , O, or S;
Z 1 and Z 2 each independently represent N or CH, while Z 1 ≠Z 2 ;
R 1 and R 2 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an acyl group, an alkoxycarbonyl group, a cyano group, a nitro group, or a hydroxy group;
R 3 and R 4 each independently represent a group represented by Chemical Formula 2, a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an acyl group, an alkoxycarbonyl group, a cyano group, a nitro group, or a hydroxy group;
wherein either of R 3 and R 4 is a group represented by Chemical Formula 2; and
R 10 represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxycarbonyl group, or a hydroxy group;
in the Chemical Formula 2,
R 5 to R 9 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an acyl group, an alkoxycarbonyl group, a cyano group, a nitro group, or a hydroxy group; and
wherein at least one of R 5 to R 9 represents an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, an acyl group having 2 to 19 carbon atoms, or an alkoxycarbonyl group having 2 to 19 carbon atoms.

2 . The compound according to claim 1 , wherein at least one of R 1 to R 4 in the Chemical Formula 1 represents a halogen atom, a cyano group, a nitro group, a hydroxy group, an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, an acyl group having 2 to 19 carbon atoms, or an alkoxycarbonyl group having 2 to 19 carbon atoms, and/or R 10 represents a halogen atom, a hydroxy group, an alkyl group having 1 to 18 carbon atoms, or an alkoxycarbonyl group having 2 to 19 carbon atoms.

3 . The compound according to claim 1 , wherein R 7 represents an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, an acyl group having 2 to 19 carbon atoms, or an alkoxycarbonyl group having 2 to 19 carbon atoms.

4 . The compound according to claim 1 , wherein R 7 represents an alkyl group having 4 to 12 carbon atoms, an alkoxy group having 4 to 12 carbon atoms, an acyl group having 5 to 13 carbon atoms, or an alkoxycarbonyl group having 5 to 13 carbon atoms.

5 . The compound according to claim 1 , wherein at least one of R 5 , R 6 , R 8 , and R 9 represents an alkyl group having 1 to 4 carbon atoms which may be branched, an alkoxy group having 1 to 4 carbon atoms which may be branched, or a halogen atom.

6 . The compound according to claim 1 , wherein a wavelength of irradiated light at the time when the compound is fluidized by being irradiated with light is 280 nm or more and 480 nm or less.

7 . A toner comprising the compound set forth in claim 1 .

8 . The toner according to claim 7 , further comprising a binder resin.

9 . The toner according to claim 8 , wherein the binder resin includes at least one selected from the group consisting of a styrene-acrylic resin and a polyester resin.

10 . The toner according to claim 7 , further comprising a colorant.

11 . The toner according to claim 7 , further comprising a release agent.

12 . An image forming method, comprising forming a toner image formed from the toner set forth in claim 7 on a recording medium; and irradiating the toner image with light and thereby softening the toner image.

13 . The image forming method according to claim 12 , wherein a wavelength of light at the time of irradiating the toner image with light and thereby softening the toner image is 280 nm or more and 480 nm or less.

14 . The image forming method according to claim 12 , further comprising pressing the toner image.

15 . The image forming method according to claim 14 , wherein in the pressing, the toner image is further heated.

16 . A photosensitive adhesive comprising the compound set forth in claim 1 .

17 . A photoresponsive compound represented by a following General Formula (1), the photoresponsive compound being fluidized by being irradiated with light and reversibly non-fluidized:

wherein in the General Formula (1), Z 1 and Z 2 each independently represent N or CH, while Z 1 ≠Z 2 ;
A and B each independently represent a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group; and
an activation energy Ea represented by a following Formula (1) is 60 kJ/mol or greater:
Ea (kJ/mol)=(Total energy of TS (kJ/mol))−(Total energy of cis-form(kJ/mol))  Formula (1):

wherein in the Formula (1), TS represents a transition state represented by General Formula (2); and the cis-form represents an isomer represented by General Formula (3):

18 . The compound according to claim 17 , wherein in the General Formula (1), A and B each independently represent a substituted or unsubstituted phenyl group or a substituted or unsubstituted aromatic heterocyclic group.

19 . The compound according to claim 18 , wherein in the General Formula (1), A and B each independently represent a substituted or unsubstituted phenyl group; and at least one of A and B has at least one substituent selected among an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, and a dialkylamino group having 2 to 10 carbon atoms.

20 . The compound according to claim 19 , wherein at least one of A and B has the substituent at a para-position with respect to Z 1 or Z 2 .

21 . The compound according to claim 20 , wherein both A and B have the substituent.

22 . The compound according to claim 19 , wherein at least one of A and B is a phenyl group unsubstituted at two ortho-positions and two meta-positions with respect to Z 1 or Z 2 , or substituted with a group selected among an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and a halogen atom.

23 . The compound according to claim 18 , wherein
one of A and B is a phenyl group substituted with at least one substituent selected among an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, and a dialkylamino group having 2 to 10 carbon atoms, and the other one is a substituted or unsubstituted aromatic heterocyclic group.

24 . The compound according to claim 23 , wherein the phenyl group has the substituent at a para-position with respect to Z 1 or Z 2 .

25 . The compound according to claim 24 , wherein
the aromatic heterocyclic group is unsubstituted, or the aromatic heterocyclic group is substituted with a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, a dialkylamino group having 2 to carbon atoms, an acyl group having 2 to 19 carbon atoms, or an alkoxycarbonyl group having 2 to 19 carbon atoms.

26 . The

Assignees

• Konica Minolta Inc

Inventors

• Kusano Yukiko
• Horiguchi Haruo
• Sugama Kouji
• Takahashi Seijiro
• Shibata Toyoko
• Hayata Hirofumi
• Oshiyama Tomohiro

Classifications

• G03G9/0922

  Formazane dyes; Nitro and Nitroso dyes; Quinone imides; Azomethine dyes · CPC title

• C07D409/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D403/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D333/22 Primary

  Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom · CPC title

• C07D307/52

  Radicals substituted by nitrogen atoms not forming part of a nitro radical · CPC title