Infrared sensitive color-forming composition, infrared curable color-forming composition, lithographic printing plate precursor and plate making method

Patent metadata

Field	Value
Publication number	US-10022996-B2
Application number	US-201514836278-A
Country	US
Kind code	B2
Filing date	Aug 26, 2015
Priority date	Feb 27, 2013
Publication date	Jul 17, 2018
Grant date	Jul 17, 2018

Abstract

The invention is directed to an infrared sensitive color-forming composition containing a compound having an infrared absorbing skeleton and a thermochromic skeleton in a molecule thereof wherein the infrared absorbing skeleton and the thermochromic skeleton are connected with a covalent bond or an ionic bond and a binder; an infrared curable color-forming composition wherein the infrared sensitive color-forming composition further contains a radical initiator and a polymerizable compound; a lithographic printing plate precursor having an image-recording layer containing the infrared curable color-forming composition on a support; a plate making method including imagewise exposing the lithographic printing plate precursor and conducting on-press development processing by supplying printing ink and dampening water on a printing machine to remove a non-image area; a compound represented by the formula (7) as defined herein; and a compound represented by the formula (8) as defined herein.

First claim

The invention claimed is:

1. An infrared sensitive color-forming composition comprising: (A) a compound having an infrared absorbing skeleton and a thermochromic skeleton in a molecule thereof wherein the infrared absorbing skeleton and the thermochromic skeleton are connected with a covalent bond or an ionic bond; and (B) a binder, wherein the infrared absorbing skeleton is a cyanine dye residue represented by the following formula (3):

wherein, in the formula (3), R 1 represents a hydrogen atom, a halogen atom, —OR 10 , —N(R 11 )(R 12 ) or —SR 13 , R 10 and R 13 each represents an alkyl group or an aryl group, R 11 and R 12 each represents a hydrogen atom, an alkyl group or an aryl group, or R 11 and R 12 may be combined with each other to form a ring, R 2 and R 3 each represents a hydrogen atom or an alkyl group, or R 2 and R 3 may be combined with each other to form a ring, Ar 1 and Ar 2 each represents an atomic group necessary for forming a benzene ring or a naphthalene ring, Y 1 and Y 2 each represents a sulfur atom or a dialkylmethylene group, R 4 and R 5 each represents an alkyl group, Za represents a counter ion for neutralizing an electric charge, and the cyanine dye residue is connected to the thermochromic skeleton in R 1 .

2. The infrared sensitive color-forming composition as claimed in claim 1 , wherein the compound is represented by the following formula (1-1):
A-B1-C1  (1-1)

wherein, in the formula (1-1), A represents a thermochromic skeleton, B1 represents a single bond or a connecting group, and C1 represents an infrared absorbing skeleton.

3. The infrared sensitive color-forming composition as claimed in claim 1 , wherein the thermochromic skeleton has a structure represented by the following formula (4):

wherein, in the formula (4), R 14 to R 22 each represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, —OR 23 , —NR 24 R 25 , —SR 26 or a nitro group, or any adjacent two of R 14 to R 22 may be combined with each other to form a ring, R 23 , R 24 , R 25 and R 26 each represents a hydrogen atom or an alkyl group, or R 24 and R 25 may be combined with each other to form a ring, X represents a carbon atom or a nitrogen atom, and the thermochromic skeleton is connected to the infrared absorbing skeleton in any of R 18 , R 20 and R 22 .

4. The infrared sensitive color-forming composition as claimed in claim 3 , wherein the thermochromic skeleton has a structure represented by the following formula (5):

wherein, in the formula (5), R 14 to R 19 each represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, —OR 23 , —NR 24 R 25 , —SR 26 or a nitro group, or any adjacent two of R 14 to R 19 may be combined with each other to form a ring, R 23 , R 24 , R 25 and R 26 each represents a hydrogen atom or an alkyl group, or R 24 and R 25 may be combined with each other to form a ring, X represents a carbon atom or a nitrogen atom, R 27 and R 28 each represents an alkyl group or an aryl group, or R 27 and R 28 may be combined with each other to form a ring, R 29 to R 32 each represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, —OR 23 , —NR 24 R 25 or —SR 26 , and the thermochromic skeleton is connected to the infrared absorbing skeleton in any of R 27 , R 28 and R 31 .

5. The infrared sensitive color-forming composition as claimed in claim 1 , wherein the compound is a compound represented by the following formula (6-1), (6-2) or (6-3):

wherein, in the formulae (6-1), (6-2) and (6-3), R 2 and R 3 each represents an alkyl group, or R 2 and R 3 may be combined with each other to form a ring, Ar 1 and Ar 2 each represents an atomic group necessary for forming a benzene ring or a naphthalene ring, Y 1 and Y 2 each represents a sulfur atom or a dialkylmethylene group, R 4 and R 5 each represents an alkyl group, R 6 , R 7 , R 8 and R 9 each represents a hydrogen atom or an alkyl group, Za represents a counter ion for neutralizing an electric charge, B 3 , B 4 and B 5 each represents a single bond or a connecting group, R 14 to R 22 each represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, —OR 23 , —NR 24 R 25 , —SR 26 or a nitro group, or any adjacent two of R 14 to R 22 may be combined with each other to form a ring, R 23 , R 24 , R 25 and R 26 each represents a hydrogen atom or an alkyl group, or R 24 and R 25 may be combined with each other to form a ring, and X represents a carbon atom or a nitrogen atom.

6. The infrared sensitive color-forming composition as claimed in claim 5 , wherein the compound is a compound represented by the following formula (6-4):

wherein, in the formula (6-4), R 2 and R 3 each represents an alkyl group, or R 2 and R 3 may be combined with each other to form a ring, Ar 1 and Ar 2 each represents an atomic group necessary for forming a benzene ring or a naphthalene ring, Y 1 and Y 2 each represents a sulfur atom or a dialkylmethylene group, R 4 and R 5 each represents an alkyl group, R 6 , R 7 , R 8 and R 9 each represents a hydrogen atom or an alkyl group, Za represents a counter ion for neutralizing an electric charge, B 6 represents an alkylene group having 10 or less carbon atoms, which may contain a nitrogen atom, R 14 to R 19 and R 21 to R 22 each represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, —OR 23 , —NR 24 R 25 , —SR 26 or a nitro group, or any adjacent two of R 14 to R 19 and R 21 to R 22 may be combined with each other to form a ring, and R 23 , R 24 , R 25 and R 26 each represents a hydrogen atom or an alkyl group, or R 24 and R 25 may be combined with each other to form a ring.

7. The infrared sensitive color-forming composition as claimed in claim 1 , wherein the compound (A) is a compound represented by the following formula (1-1):
A-B1-C1  (1-1)

wherein A is a thermochromic skeleton, B1 is a single bond or a connecting group, and C1 is an infrared absorbing skeleton,
wherein the connecting group B1 is selected from the following structures:

wherein
* represents a site which connects to the thermochomic skeleton,
** represents a site which connects to the infrared absorbing skeleton,
f, g and h each represents an integer from 1 to 6,
i, j, k and l each represents an integer from 0 to 6,
D represents —N(Ra)—, —O—, —S— or —C(Rb)(Rc)-, and
Ra, Rb and Rc each represents a hydrogen atom or an alkyl group; and
the infrared absorbing skeleton C1 is a cyanine dye of formula (3) as set forth in claim 1 .

Assignees

• Fujifilm Corp

Inventors

• Mizuno Akio
• Suzuki Shota
• Sato Noriaki

Classifications

• C09B23/0025

  the substituent being bound through an oxygen atom · CPC title

• B41M5/3372

  Macromolecular compounds · CPC title

• C09B23/086

  more than five >CH- groups · CPC title

• C09B57/00

  Other synthetic dyes of known constitution · CPC title

• C09B69/06

  of cationic dyes with organic acids {or with inorganic complex acids} · CPC title