U.S. patent application number 10/095448 was filed with the patent office on 2002-09-12 for azomethine compound and oily magenta ink.
This patent application is currently assigned to FUJI PHOTO FILM CO., LTD.. Invention is credited to Asanuma, Naoki, Mikoshiba, Hisashi, Motoki, Masuji, Sato, Tadahisa, Suzuki, Ryo, Yamakawa, Katsuyoshi.
Application Number | 20020128488 10/095448 |
Document ID | / |
Family ID | 13324089 |
Filed Date | 2002-09-12 |
United States Patent
Application |
20020128488 |
Kind Code |
A1 |
Yamakawa, Katsuyoshi ; et
al. |
September 12, 2002 |
Azomethine compound and oily magenta ink
Abstract
An azomethine compound is represented by the formula (I). 1 and
R.sup.1, L.sup.1, L.sup.2, R.sup.3 and R.sup.4 have 20 to 50 carbon
atoms in total.
Inventors: |
Yamakawa, Katsuyoshi;
(Minami-ashigara-shi, JP) ; Motoki, Masuji;
(Minami-ashigara-shi, JP) ; Asanuma, Naoki;
(Minami-ashigara-shi, JP) ; Suzuki, Ryo;
(Minami-ashigara-shi, JP) ; Sato, Tadahisa;
(Minami-ashigara-shi, JP) ; Mikoshiba, Hisashi;
(Minami-ashigara-shi, JP) |
Correspondence
Address: |
SUGHRUE, MION, ZINN, MACPEAK & SEAS
2100 Pennsylvania Avenue, N.W.
Washington
DC
20037-3202
US
|
Assignee: |
FUJI PHOTO FILM CO., LTD.
|
Family ID: |
13324089 |
Appl. No.: |
10/095448 |
Filed: |
March 13, 2002 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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10095448 |
Mar 13, 2002 |
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09515846 |
Feb 29, 2000 |
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6383276 |
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Current U.S.
Class: |
548/262.4 |
Current CPC
Class: |
C09B 55/009 20130101;
C09D 11/328 20130101; C09D 11/32 20130101 |
Class at
Publication: |
548/262.4 |
International
Class: |
C07D 471/04 |
Foreign Application Data
Date |
Code |
Application Number |
Mar 12, 1999 |
JP |
11-066722 |
Claims
1. An azomethine compound represented by the formula (I): 12R.sup.1
is an alkyl group having 1 to 16 carbon atoms; R.sup.2 is a halogen
atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group
having 1 to 20 carbon atoms, an amido group having 2 to 20 carbon
atoms, an alkoxycarbonylamino group having 2 to 20 carbon atoms,
nitro or cyano; R.sup.3 is an alkyl group having 1 to 30 carbon
atoms, an aryl group having 6 to 30 carbon atoms, an aryloxyalkyl
group having 7 to 30 carbon atoms or an alkoxycarbonylalkyl group
having 3 to 30 carbon atoms; R.sup.4 is an alkyl group having 1 to
16 carbon atoms; L.sup.1 is an alkylene group having 1 to 30 carbon
atoms or an arylene group having 6 to 30 carbon atoms; L.sup.2 is
--CO--NH--, --SO.sub.2--NH--, --O--, --O--CO--or --O----CO--NH--; X
is cyano, an alkoxycarbonyl group having 2 to 19 carbon atoms, an
alkylsulfonyl group having 1 to 18 carbon atoms, an arylsulfonyl
group having 6 to 26 carbon atoms, sulfamoyl, an alkylsulfamoyl
group having 1 to 18 carbon atoms or an arylsulfamoyl group having
6 to 26 carbon atoms; Y is hydrogen, a halogen atom, hydroxyl, an
alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6
to 20 carbon atoms or an acyloxy group having 2 to 20 carbon atoms;
m is 1, 2, 3 or 4; n is an integer of 1 to 18; p is 0, 1, 2, 3 or
4; and R.sup.1, L.sup.1, L.sup.2, R.sup.3 and R.sup.4 have 20 to 50
carbon atoms in total.
2. The azomethine compound as defined in claim 1, wherein R.sup.1
is an alkyl group having 1 to 12 carbon atoms.
3. The azomethine compound as defined in claim 1, wherein R.sup.2
is a halogen atom, an alkyl group having 1 to 12 carbon atoms, an
alkoxy group having 1 to 12 carbon atoms, an amido group having 2
to 12 carbon atoms, an alkoxycarbonylamino group having 2 to 12
carbon atoms, nitro or cyano.
4. The azomethine compound as defined in claim 1, wherein R.sup.3
is an alkyl group having 1 to 25 carbon atoms, an aryl group having
6 to 25 carbon atoms, an aryloxyalkyl group having 7 to 25 carbon
atoms or an alkoxycarbonylalkyl group having 3 to 25 carbon
atoms.
5. The azomethine compound as defined in claim 1, wherein R.sup.4
is an alkyl group having 1 to 12 carbon atoms.
6. The azomethine compound as defined in claim 1, wherein L.sup.1
is an alkylene group having 1 to 25 carbon atoms or an arylene
group having 6 to 25 carbon atoms.
7. The azomethine compound as defined in claim 1, wherein X is
cyano or an alkoxycarbonyl group having 2 to 19 carbon atoms.
8. The azomethine compound as defined in claim 1, wherein Y is
hydrogen.
9. The azomethine compound as defined in claim 1, wherein m is 1, 2
or 3.
10. The azomethine compound as defined in claim 1, wherein n is an
integer of 1 to 14.
11. The azomethine compound as defined in claim 1, wherein p is 0,
1, 2 or 3.
12. The azomethine compound as defined in claim 1, wherein R.sup.1,
L.sup.1, L.sup.2, R.sup.3 and R.sup.4 have 25 to 45 carbon atoms in
total.
13. An azomethine compound represented by the formula (Ia):
13wherein R.sup.1 is an alkyl group having 1 to 16 carbon atoms;
R.sup.2 is a halogen atom, an alkyl group having 1 to 20 carbon
atoms, an alkoxy group having 1 to 20 carbon atoms, an amido group
having 2 to 20 carbon atoms, an alkoxycarbonylamino group having 2
to 20 carbon atoms, nitro or cyano; R.sup.3 is an alkyl group
having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon
atoms, an aryloxyalkyl group having 7 to 30 carbon atoms or an
alkoxycarbonylalkyl group having 3 to 30 carbon atoms; L.sup.1 is
an alkylene group having 1 to 30 carbon atoms or an arylene group
having 6 to 30 carbon atoms; L.sup.2 is --CO--NH--,
--SO.sub.2--NH--, --O--, ----O --CO--or --O--CO--NH--; X is cyano,
an alkoxycarbonyl group having 2 to 19 carbon atoms, an
alkylsulfonyl group having 1 to 18 carbon atoms, an arylsulfonyl
group having 6 to 26 carbon atoms, sulfamoyl, an alkylsulfamoyl
group having 1 to 18 carbon atoms or an arylsulfamoyl group having
6 to 26 carbon atoms; Y is hydrogen, a halogen atom, hydroxyl, an
alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6
to 20 carbon atoms or an acyloxy group having 2 to 20 carbon atoms;
m is 1, 2, 3 or 4; n is an integer of 1 to 18; p is 0, 1, 2, 3 or
4; and R.sup.1, L.sup.1, L.sup.2, R.sup.3 and R.sup.4 have 20 to 50
carbon atoms in total.
14. An oily magenta ink in which an azomethine dye represented by
the formula (I) is dissolved in an organic solvent: 14R.sup.1 is an
alkyl group having 1 to 16 carbon atoms; R.sup.2 is a halogen atom,
an alkyl group having 1 to 20 carbon atoms, an alkoxy group having
1 to 20 carbon atoms, an amido group having 2 to 20 carbon atoms,
an alkoxycarbonylamino group having 2 to 20 carbon atoms, nitro or
cyano; R.sup.3 is an alkyl group having 1 to 30 carbon atoms, an
aryl group having 6 to 30 carbon atoms, an aryloxyalkyl group
having 7 to 30 carbon atoms or an alkoxycarbonylalkyl group having
3 to 30 carbon atoms; R.sup.4 is an alkyl group having 1 to 16
carbon atoms; L.sup.1 is an alkylene group having 1 to 30 carbon
atoms or an arylene group having 6 to 30 carbon atoms; L.sup.2 is
--CO--NH--, --SO.sub.2--NH--, --O--, --O--CO--or --O--CO--NH--; X
is cyano, an alkoxycarbonyl group having 2 to 19 carbon atoms, an
alkylsulfonyl group having 1 to 18 carbon atoms, an arylsulfonyl
group having 6 to 26 carbon atoms, sulfamoyl, an alkylsulfamoyl
group having 1 to 18 carbon atoms or an arylsulfamoyl group having
6 to 26 carbon atoms; Y is hydrogen, a halogen atom, hydroxyl, an
alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6
to 20 carbon atoms or an acyloxy group having 2 to 20 carbon atoms;
m is 1, 2, 3 or 4; n is an integer of 1 to 25 18; p is 0, 1, 2, 3
or 4; and R.sup.1, L.sup.1, L.sup.2, R.sup.3 and R.sup.4 have 20 to
50 carbon atoms in total.
Description
FIELD OF THE INVENTION
[0001] The present invention relates to an azomethine compound. In
detail, the invention relates to an azomethine compound suitable
for a jet printing ink of magenta color.
BACKGROUND OF THE INVENTION
[0002] In an ink-jet recording method, images or characters are
printed on image-receiving material with ink ejected from very fine
nozzles. The ink-jet recording method can be conducted by using a
relatively inexpensive apparatus (i.e., an ink-jet printer), as
compared with other printing methods. Further, in proportion to
improvement of the method, images of high qualities have been given
recently. Now, the ink-jet recording method is one of the most
popular image-recording methods.
[0003] Ink for the ink-jet recording method (i.e., jet printing
ink) must not choke the fine nozzles. Since aqueous inks (aqueous
solutions of dyes) hardly choke the nozzles, they are widely used.
However, the aqueous inks have poor water resistance. Various means
(described in Japanese Patent Provisional Publication Nos.
4(1992)-28776, 4(1992)-189876, 4(1992)-261478, 4(1992)-359071 and
4(1992)-359072) have been proposed to improve the water resistance
of the aqueous inks or water-soluble dyes. In addition, the
water-soluble dyes have poor light resistance.
[0004] Oil-soluble dyes (described in Japanese Patent Provisional
Publication Nos. 1(1989)-170672, 3(1991)-221137, 7(1995)-96163,
8(1996)-218015, 9(1997)-3376, 9(1997)-241565, 9(1997)-286939 and
10(1998)-279873) have been proposed in place of the water-soluble
dyes. The oil-soluble dyes are usually incorporated in
microcapsules or soaked in polymers when they are used for ink-jet
printing. Although the oil-soluble dyes have satisfying water
resistance, they are unsatisfactory in color reproduction and color
stability.
SUMMARY OF THE INVENTION
[0005] Water-soluble dyes for ink-jet recording have poor
resistance against water and light, while oil-soluble dyes are
unsatisfactory in color reproduction and color stability.
[0006] An object of the present invention is to provide an
oil-soluble dye excellent in color reproduction and color
stability.
[0007] Another object of the invention is to provide an azomethine
compound suitable for a jet printing ink of magenta color.
[0008] A further object of the invention is to provide an oily
magenta ink for ink-jet recording.
[0009] The applicants have found an azomethine compound having
light-absorption characteristics suitable for a magenta dye. The
compound is oil-soluble, and is advantageously used in a
preparation of an oily magenta ink for ink-jet recording.
[0010] The present invention provides an azomethine compound
represented by the formula (I): 2
[0011] R.sup.1 is an alkyl group having 1 to 16 carbon atoms;
R.sup.2 is a halogen atom, an alkyl group having 1 to 20 carbon
atoms, an alkoxy group having 1 to 20 carbon atoms, an amido group
having 2 to 20 carbon atoms, an alkoxycarbonylamino group having 2
to 20 carbon atoms, nitro or cyano; R.sup.3 is an alkyl group
having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon
atoms, an aryloxyalkyl group having 7 to 30 carbon atoms or an
alkoxycarbonylalkyl group having 3 to 30 carbon atoms; R.sup.4 is
an alkyl group having 1 to 16 carbon atoms; L.sup.l is an alkylene
group having 1 to 30 carbon atoms or an arylene group having 6 to
30 carbon atoms; L.sup.2 is --CO--NH--, --SO.sub.2 --NH--, --O--,
--O--CO--or --O--CO--NH--; X is cyano, an alkoxycarbonyl group
having 2 to 19 carbon atoms, an alkylsulfonyl group having 1 to 18
carbon atoms, an arylsulfonyl group having 6 to 26 carbon atoms,
sulfamoyl, an alkylsulfamoyl group having 1 to 18 carbon atoms or
an arylsulfamoyl group having 6 to 26 carbon atoms; Y is hydrogen,
a halogen atom, hydroxyl, an alkoxy group having 1 to 20 carbon
atoms, an aryloxy group having 6 to 20 carbon atoms or an acyloxy
group having 2 to 20 carbon atoms; m is 1, 2, 3 or 4; n is an
integer of 1 to 18; p is 0, 1, 2, 3 or 4; and R.sup.1, L.sup.1,
L.sup.2, R.sup.3 and R.sup.4 have 20 to 50 carbon atoms in
total.
[0012] The invention also provides an oily magenta ink in which an
azomethine dye represented by the formula (I) is dissolved in an
organic solvent.
[0013] The azomethine compound represented by the formula (I) has
excellent characteristics suitable for a magenta dye. Accordingly,
the azomethine compound can be advantageously used in a preparation
of an oily magenta ink for ink-jet recording.
[0014] Further, the azomethine compound represented by the formula
(I) is excellent in stability to light and heat. Accordingly, the
azomethine compound can be used a magenta dye that is excellent in
a light resistance and in a heat resistance.
DETAILED DESCRIPTION OF THE INVENTION
[0015] The azomethine compound represented by the formula (I) can
be classified into the three embodiments represented by the
formulas (Ia), (Ib) and (Ic), respectively. The embodiment of the
formula (Ia) is particularly preferred. 3
[0016] In the formulas (Ia) to (Ic), R.sup.1 is an alkyl group
having 1 to 16 carbon atoms. The alkyl group preferably has 1 to 12
carbon atoms, more preferably has 1 to 8 carbon atoms, further
preferably has 1 to 6 carbon atoms, and most preferably has 1 to 4
carbon atoms. The alkyl group can have a branched chain. Examples
of the alkyl groups include methyl and t-butyl.
[0017] In the formulas (Ia) to (Ic), R.sup.2 is a halogen atom, an
alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1
to 20 carbon atoms, an amido group having 2 to 20 carbon atoms, an
alkoxycarbonylamino group having 2 to 20 carbon atoms, nitro or
cyano.
[0018] The alkyl group preferably has 1 to 12 carbon atoms, more
preferably has 1 to 8 carbon atoms, further preferably has 1 to 4
carbon atoms, and most preferably has 1 or 2 carbon atoms. The
alkyl group can have a branched chain. Examples of the alkyl groups
include methyl and ethyl.
[0019] The alkoxy group preferably has 1 to 12 carbon atoms, more
preferably has 1 to 8 carbon atoms, further preferably has 1 to 4
carbon atoms, and most preferably has 1 or 2 carbon atoms. The
alkoxy group can have a branched chain. Examples of the alkoxy
groups include methoxy.
[0020] The amido group preferably has 2 to 12 carbon atoms, more
preferably has 2 to 8 carbon atoms, further preferably has 2 to 6
carbon atoms, and most preferably has 3 or 4 carbon atoms. Examples
of the amido groups include acetamido.
[0021] The alkoxycarbonylamino group preferably has 2 to 12 carbon
atoms, more preferably has 2 to 8 carbon atoms, further preferably
has 2 to 6 carbon atoms, and most preferably has 2 or 3 carbon
atoms. Examples of the alkoxycarbonylamino groups include
methoxycarbonylamino.
[0022] In the formulas (Ia) to (Ic) , R.sup.3 is an alkyl group
having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon
atoms, an aryloxyalkyl group having 7 to 30 carbon atoms or an
alkoxylcarbonylalkyl group having 3 to 30 carbon atoms.
[0023] The alkyl group preferably has 2 to 25, more preferably has
3 to 20 carbon atoms, and most preferably has 4 to 16 carbon atoms.
The alkyl group can have a branched chain.
[0024] Examples of the aryl groups include phenyl and naphthyl.
Phenyl is preferred. The aryl group can have a substituent group.
Examples of the substituent groups include a halogen atom, an alkyl
group having 1 to 24 carbon atoms and an alkoxy group having 1 to
24 carbon atoms. The aryl group has 6 to 30 carbon atoms,
preferably 6 to 25 carbon atoms, more preferably 6 to 20 carbon
atoms, and most preferably 6 to 16 carbon atoms. The number of the
carbon atoms means the number of the total carbon atoms contained
in the aryl group and the substituent group.
[0025] The alkyl moiety of the aryloxyalkyl group can have a
branched chain. The aryl moiety of the aryloxyalkyl group is
preferably phenyl. The aryloxyalkyl group can have a substituent
group. Examples of the substituent groups include a halogen atom,
an alkyl group having 1 to 23 carbon atoms and an alkoxy group
having 1 to 23 carbon atoms. The aryloxyalkyl group has 7 to 30
carbon atoms, preferably has 7 to 25 carbon atoms, more preferably
7 to 20 carbon atoms, and further preferably 7 to 16 carbon atoms.
The number of the carbon atoms means the number of the total carbon
atoms contained in the aryloxyalkyl group and the substituent
group.
[0026] The alkoxycarbonylalkyl group preferably has 3 to 25 carbon
atoms, more preferably has 4 to 20 carbon atoms, and most
preferably has 5 to 16 carbon atoms. Each of the two alkyl moieties
of the alkoxycarbonylalkyl group can have a branched chain.
[0027] In the formula (Ic) , R.sup.4 is an alkyl group having 1 to
16 carbon atoms. The alkyl group preferably has 1 to 12 carbon
atoms, more preferably has 1 to 8 carbon atoms, further preferably
has 1 to 6 carbon atoms, and most preferably has 1 to 4 carbon
atoms. The alkyl group can have a branched chain. Examples of the
alkyl groups include methyl and ethyl.
[0028] In the formulas (Ia) to (Ic), L.sup.1 is an alkylene group
having 1 to 30 carbon atoms or an arylene group having 6 to 30
carbon atoms.
[0029] The alkylene group preferably has 1 to 25 carbon atoms, more
preferably has 2 to 20 carbon atoms, and most preferably has 2 to
16 carbon atoms. The alkylene group can have a branched chain.
[0030] Examples of the arylene groups include phenylene and
naphthylene. Phenylene is preferred. The arylene group can have a
substituent group. Examples of the substituent groups include a
halogen atom, an alkyl group having 1 to 24 carbon atoms and an
alkoxy group having 1 to 24 carbon atoms. The arylene group has 6
to 30 carbon atoms, preferably 6 to 25 carbon atoms, more
preferably 6 to 20 carbon atoms, and most preferably 6 to 16 carbon
atoms. The number of the carbon atoms means the number of the total
carbon atoms contained in the arylene group and the substituent
group. In the formulas (Ia) to (Ic), L.sup.2 is --CO--NH--,
--SO.sub.2--NH--, --O--, ----O--CO--or --O--CO--NH--, in each of
which the left side is attached to R.sup.3, and the right side is
attached L.sup.1.
[0031] In the formulas (Ia) to (Ic), X is cyano, an alkoxy-carbonyl
group having 2 to 19 carbon atoms, an alkylsulfonyl group having 1
to 18 carbon atoms, an arylsulfonyl group having 6 to 26 carbon
atoms, sulfamoyl, an alkylsulfamoyl group having 1 to 18 carbon
atoms or an arylsulfamoyl group having 6 to 26 carbon atoms. Cyano
and an alkoxycarbonyl group having 2 to 19 carbon atoms are
preferred, and cyano is most preferred.
[0032] The alkoxycarbonyl group preferably has 2 to 8 carbon atoms.
Examples of the alkoxycarbonyl groups include methoxycarbonyl and
dodecyloxycarbonyl.
[0033] The alkylsulfonyl group preferably has 1 to 7 carbon atoms.
Examples of the alkylsulfonyl groups include methanesulfonyl.
[0034] The aryl moiety of the arylsulfonyl group is preferably
phenyl. The arylsulfonyl group can have a substituent group.
Examples of the substituent groups include a halogen atom, an alkyl
group having 1 to 20 carbon atoms and an alkoxy group having 1 to
20 carbon atoms. The arylsulfonyl group has 6 to 26 carbon atom,
and preferably has 6 to 15 carbon atoms. The number of the carbon
atoms means the number of the total carbon atoms contained in the
arylsulfonyl group and the substituent group. Examples of the
arylsulfonyl groups include benzenesulfonyl.
[0035] The alkylsulfamoyl group preferably has 1 to 9 carbon atoms.
Examples of the alkylsulfamoyl groups include methylsulfamoyl.
[0036] The aryl moiety of the arylsulfamoyl group is preferably
phenyl. The arylsulfamoyl group can have a substituent group.
Examples of the substituent groups include a halogen atom, an alkyl
group having 1 to 20 carbon atoms and an alkoxy group having 1 to
20 carbon atoms. The arylsulfamoyl group has 6 to 26 carbon atoms,
and preferably has 6 to 15 carbon atoms. The number of the carbon
atoms means the number of the total carbon atoms contained in the
arylsulfamoyl group and the substituent group. Examples of the
arylsulfamoyl groups include phenylsulfamoyl.
[0037] In the formulas (Ia) to (Ic), Y is hydrogen, a halogen atom,
hydroxyl, an alkoxy group having 1 to 20 carbon atoms, an aryloxy
group having 6 to 20 carbon atoms or an acyloxy group having 2 to
20 carbon atoms. Hydrogen atom is particularly preferred.
[0038] The alkoxy group preferably has 1 to 12 carbon atoms, more
preferably has 1 to 8 carbon atoms, further preferably has 1 to 4
carbon atoms, and most preferably has 1 or 2 carbon atoms. The
alkoxy group can have a branched chain. Examples of the alkoxy
groups include methoxy and ethoxy.
[0039] The aryl moiety of the aryloxy group is preferably phenyl.
The aryloxy group can have a substituent group. Examples of the
substituent groups include a halogen atom, an alkyl group having 1
to 14 carbon atoms and an alkoxy group having 1 to 14carbon atoms.
The aryloxy group has 6 to 20 carbon atoms, and preferably has 6 to
15 carbon atoms. The number of the carbon atoms means the number of
the total carbon atoms contained in the aryloxy group and the
substituent group. Examples of the aryloxy groups include
phenoxy.
[0040] The acyloxy group preferably has 1 to 12 carbon atoms, more
preferably has 1 to 8 carbon atoms, further preferably has 1 to 4
carbon atoms, and most preferably has 2 or 3 carbon atoms. Examples
of the acyloxy groups include acetoxy.
[0041] In the formulas (Ia) to (Ic), m is an integer of 1 to 4,
preferably is an integer of 1 to 3, and more preferably is 1 or 2.
In the case that m is 2, 3 or 4, (CH.sub.2).sub.m means an alkylene
group of a straight chain.
[0042] In the formulas (Ia) to (Ic), n is an integer of 1 to 18,
preferably is an integer of 1 to 14, more preferably is an integer
of 1 or 10, further preferably is an integer of 1 to 8, and most
preferably is an integer of 1 to 6. In the case that n is 2 or
more, the alkylene group represented by C.sub.n H.sub.2n can have a
branched chain.
[0043] In the formulas (Ia) to (Ic), p is 0, 1, 2, 3 or 4,
preferably is 0, 1, 2 or 3, more preferably is 0, 1 or 2, further
preferably is 0 or 1, and most preferably is 0. In the case that p
is 2, 3 or 4, the groups represented by R.sup.2 can be different
from each other.
[0044] In the formulas (Ia) and (Ib), R.sup.1, L.sup.1, L.sup.2 and
R.sup.3 have 20 to 50 carbon atoms in total. In the formula (Ic),
R.sup.1, L.sup.1, L.sup.2, R.sup.3 and R.sup.4 have 20 to 50 carbon
atoms in total. The total number of the carbon atoms preferably is
25 to 45.
[0045] The azomethine compound of the formula (I) preferably has a
molecular weight of 600 to 2,000, and more preferably has a
molecular weight of 800 to 1,500.
[0046] Examples of the azomethine compounds represented by the
formula (I) are shown below. 4
[0047] (Ia-1)
[0048] R.sup.1: CH.sub.3, R.sup.21: H, R.sup.22: H,
[0049] R.sup.3: 1-(2,4-di-t-pentylphenoxy)heptyl,
[0050] L.sup.1: --CH.sub.2--CH(CH.sub.3)--, L.sup.2: --CO--NH--, X:
cyano,
[0051] Y: H, m: 2, n: 2,
[0052] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 28
[0053] (Ia-2)
[0054] R.sup.1: CH.sub.3, R.sup.21: H, R.sup.22: H,
[0055] R.sup.3: 2-octyloxy-5-t-octylphenyl,
[0056] L.sup.1: --CH.sub.2--CH(CH.sub.3)--, L.sup.2:
--SO.sub.2--NH--, X: cyano,
[0057] Y: H, m: 2, n: 4,
[0058] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 26
[0059] (Ia-3)
[0060] R.sup.1: CH.sub.3, R.sup.21: H, R.sup.22: H,
[0061] R.sup.3:
2-octyloxy-5-(2-octyloxy-5-t-octylphenylsulfone-amido)phen- yl,
[0062] L.sup.1: --CH.sub.2--CH(CH.sub.3)--, L.sup.2:
--SO.sub.2--NH--, X: cyano,
[0063] Y: H, m: 2, n: 1,
[0064] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 40
[0065] (Ia-4)
[0066] R.sup.1: CH.sub.3, R.sup.21: H, R.sup.22: H,
[0067] R.sup.3: 2-tetradecyloxycarbonylethyl,
[0068] L.sup.1: --CH.sub.2--CH(CH.sub.3)--, L.sup.2:
--CO--NH--,
[0069] X: ethoxycarbonyl, Y: H, m: 2, n: 4,
[0070] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 22
[0071] (Ia-5)
[0072] R.sup.1: CH.sub.3, R.sup.21: CH.sub.3, R.sup.22: H, R.sup.3:
pentadecyl,
[0073] L.sup.1: -1,4-phenylene-, L.sup.2: --CO--NH--, X: cyano,
[0074] Y: H, m: 2, n: 4,
[0075] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 23
[0076] (Ia-6)
[0077] R.sup.1: CH.sub.3, R.sup.21: CH.sub.3, R.sup.22: H,
[0078] R.sup.3: 1-(2,4-di-t-pentylphenoxy)heptyl,
[0079] L.sup.1: --CH.sub.2--CH(CH.sub.3)--, L.sup.2: --CO--NH--, X:
cyano,
[0080] Y: OH, m: 2, n: 2,
[0081] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 28
[0082] (Ia-7)
[0083] R.sup.1: CH.sub.3, R.sup.21: H, R.sup.22: H, R.sup.3:
octadecyl,
[0084] L.sup.1: --CH2--CH2--, L.sup.2: --O--, X:
methoxycarbonyl,
[0085] Y: H, m: 1, n: 2,
[0086] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 21
[0087] (Ia-8)
[0088] R.sup.1: CH.sub.3, R.sup.21: H, R.sup.22: H, R.sup.3:
hexadecyl,
[0089] L.sup.1: -1,3-phenylene-, L.sup.2: --O--CO--, X: cyano,
[0090] Y: H, m: 3, n: 4,
[0091] Total number of carbon atoms in R.sup.1, L.sup.l, L.sup.2
and R.sup.3: 24
[0092] (Ia-9)
[0093] R.sup.1: t--C.sub.4H.sub.9, R.sup.21: H, R.sup.22: H,
[0094] R.sup.3:1-(2,4-di-t-pentylphenoxy)pentyl,
[0095] L.sup.1: --CH.sub.2--CH(CH.sub.3)--, L.sup.2: --CO--NH--, X:
cyano,
[0096] Y: H, m: 2, n: 2,
[0097] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 29
[0098] (Ia-10)
[0099] R.sup.1: t--C.sub.4H.sub.9, R.sup.21: H, R.sup.22: H,
[0100] R.sup.3:2-(2-methoxy)ethoxy-5-t-octylphenyl,
[0101] L.sup.1: --CH.sub.2--CH(CH.sub.3)--, L.sup.2:
--SO.sub.2--NH--, X: cyano,
[0102] Y: H, m: 2, n: 4,
[0103] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 24
[0104] (Ia-11)
[0105] R.sup.1: t--C.sub.4H.sub.9, R.sup.21: H, R.sup.22: H,
R.sup.3: tridecyl,
[0106] L.sup.1: -1,3-phenylene-, L.sup.2: --CO--NH--, X: cyano,
[0107] Y: H, m: 2, n: 2,
[0108] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 24
[0109] (Ia-12)
[0110] R.sup.1: t--C.sub.4H.sub.9, R.sup.21: H, R.sup.22: H,
[0111] R.sup.3:2-tetradecyloxycarbonylethyl,
[0112] L.sup.1: -1,4-phenylene-, L.sup.2: --CO--NH--, X: cyano,
[0113] Y: H, m: 2, n: 4,
[0114] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 28
[0115] (Ia-13)
[0116] R.sup.1: t--C.sub.4H.sub.9, R.sup.21: H, R.sup.22: H,
[0117] R.sup.3:1-(2,4-di-t-pentylphenoxy)heptyl,
[0118] L.sup.1: -1,4-phenylene-, L.sup.2: --CO--NH--, X: cyano,
[0119] Y: H, m: 2, n: 2,
[0120] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 34
[0121] (Ia-14)
[0122] R.sup.1: t--C.sub.4H.sub.9, R.sup.21: H, R.sup.22: H,
[0123] R.sup.3:1-(2,4-di-t-pentylphenoxy)heptyl,
[0124] L.sup.1: -1,4-phenylene-, L.sup.2: --CO--NH--, X: cyano,
[0125] Y: H, m: 2, n: 4,
[0126] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 34
[0127] (Ia-15)
[0128] R.sup.1: t--C.sub.4H.sub.9, R.sup.21: CH.sub.3, R.sup.22:
H,
[0129] R.sup.3:1-(2,4-di-t-pentylphenoxy)heptyl,
[0130] L.sup.1: -1,4-phenylene-, L.sup.2: --CO--NH--, X: cyano,
[0131] Y: OH, m: 2, n: 2,
[0132] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 34
[0133] (Ia-16)
[0134] R.sup.1: t--C.sub.4H.sub.9, R.sup.21: CH.sub.3, R.sup.22:
H,
[0135] R.sup.3:2-tetradecyloxycarbonylethyl,
[0136] L.sup.1: -1,4-phenylene-, L.sup.2: --CO--NH--, X: cyano,
[0137] Y: H, m: 2, n: 4,
[0138] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 28
[0139] (Ia-17)
[0140] R.sup.1: t--C.sub.4H.sub.9, R.sup.21: CH.sub.3, R.sup.22: H,
R.sup.3: heptadecyl,
[0141] L.sup.1: -1,2-phenylene-, L.sup.2: --CO--NH--,
[0142] X: methoxycarbonyl, Y: H, m: 1, n: 1,
[0143] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 28
[0144] (Ia-18)
[0145] R.sup.1: t--C.sub.4H.sub.9, R.sup.21: NHCOCH.sub.3,
R.sup.22: H,
[0146] R.sup.3: hexadecyl, L.sup.1: -1,3-phenylene-,
[0147] L.sup.2: --SO.sub.2--NH--, X: cyano, Y: acetoxy,
[0148] m: 1, n: 2,
[0149] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 26
[0150] (Ia-19)
[0151] R.sup.1: t--C.sub.4H.sub.9, R.sup.21 OCH.sub.3, R.sup.22:
H,
[0152] R.sup.3: octadecyl, L.sup.1: -1,4-phenylene-,
[0153] L.sup.2: --O--, X: sulfamoyl, Y: phenoxy,
[0154] m: 3, n: 2,
[0155] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 28
[0156] (Ia-20)
[0157] R.sup.1: t--C.sub.4H.sub.9, R.sup.21: H, R.sup.22:
OCH.sub.3,
[0158] R.sup.3: hexadecyl, L.sup.1: -3-chloro-1,4-phenylene-,
[0159] L.sup.2: --O--, X: methanesulfonyl, Y: methoxy,
[0160] m: 4, n: 2,
[0161] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 26
[0162] (Ia-21)
[0163] R.sup.1: C.sub.2H.sub.5, R.sup.21: H, R.sup.22: H, R.sup.3:
pentadecyl,
[0164] L.sup.1: --CH.sub.2--CH(CH.sub.3)--, L.sup.2: --CO--NH--, X:
cyano,
[0165] Y: H, m: 2, n: 2,
[0166] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 21
[0167] (Ia-22)
[0168] R.sup.1: C.sub.3H.sub.7, R.sup.21: H, R.sup.22: H, R.sup.3:
pentadecyl,
[0169] L.sup.1: --CH.sub.2--CH(CH.sub.3)--, L.sup.2: --CO--NH--, X:
cyano,
[0170] Y: H, m: 2, n: 4,
[0171] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 22
[0172] (Ia-23)
[0173] R.sup.1: C.sub.7H.sub.15, R.sup.21: CH.sub.3, R.sup.22:
H,
[0174] R.sup.3:2-tetradecyloxycarbonylethyl,
[0175] L.sup.1: -1,4-phenylene-, L.sup.2: --CO--NH--, X: cyano,
[0176] Y: H, m: 2,n: 4,
[0177] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 31
[0178] (Ia-24)
[0179] R.sup.1: C.sub.4H.sub.9, R.sup.21 H, R.sup.22: H,
[0180] R.sup.3:2-tetradecyloxycarbonylethyl,
[0181] L.sup.1: -1,4-phenylene-, L.sup.2: --CO--NH--,
[0182] X: butoxycarbonyl, Y: H, m: 2, n: 2,
[0183] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 28
[0184] (Ia-25)
[0185] R.sup.1: C.sub.3H.sub.7, R.sup.21: H, R.sup.22: H,
[0186] R.sup.3:2-tetradecyloxycarbonylethyl,
[0187] L.sup.1: -1,4-phenylene-, L.sup.2: --CO--NH--, X: cyano,
[0188] Y: OH, m: 3, n: 2,
[0189] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 27
[0190] (Ia-26)
[0191] R.sup.1: C.sub.2H.sub.5, R.sup.21: H, R.sup.22: H,
[0192] R.sup.3:2-tetradecyloxycarbonylethyl,
[0193] L.sup.1: -1,4-phenylene-, L.sup.2: --CO--NH--,
[0194] X: cyano, Y: methoxy, m: 3, n: 2,
[0195] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 26 5
[0196] (Ib-1)
[0197] R.sup.1: CH.sub.3, R.sup.2: H,
[0198] R.sup.3:1-(2,4-di-t-butylphenoxy)heptyl,
[0199] L.sup.1: -1,3-phenylene-, L.sup.2: --CO--NH--,
[0200] X: methanesulfonyl, Y: H, m: 2, n: 4,
[0201] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 29
[0202] (Ib-2)
[0203] R.sup.1: CH.sub.3, R.sup.2: CH.sub.3, R.sup.3:
tetradecyl,
[0204] L.sup.1: -3-chloro-1,4-phenylene-, L.sup.2: --O--,
[0205] X: cyano, Y: OH, m: 2, n: 2,
[0206] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 21
[0207] (Ib-3)
[0208] R.sup.1: CH.sub.3, R.sup.2: NHCO.sub.2CH.sub.3, R.sup.3:
hexadecyl,
[0209] L.sup.1: -1,2-phenylene-, L.sup.2: --O--,
[0210] X: sulfamoyl, Y: H, m: 2, n: 1,
[0211] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 23
[0212] (Ib-4)
[0213] R.sup.1: CH.sub.3, R.sup.2: CN, R.sup.3: pentadecyl,
[0214] L.sup.1: --CH.sub.2--CH(CH.sub.3)--, L.sup.2:
--CO--NH--,
[0215] X: N,N--dimethylsulfamoyl, Y: H,
[0216] m: 4, n: 1,
[0217] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2
and R.sup.3: 20 6
[0218] (Ic-1)
[0219] R.sup.1: CH.sub.3, R.sup.3: heptadecyl, R.sup.4:
CH.sub.3,
[0220] L.sup.1: --CH.sub.2--CH(CH.sub.3)--, L.sup.2: --CO--NH--, X:
cyano,
[0221] Y: H, m: 2, n: 4,
[0222] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2,
R.sup.3 and R.sup.4: 23
[0223] (Ic-2)
[0224] R.sup.1: t--C.sub.4H.sub.9,
R.sup.3:2-tetradecyloxycarbonylethyl,
[0225] R.sup.4: C.sub.2H.sub.5, L.sup.1: -1,4-phenylene-,
[0226] L.sup.2: --O--CO--NH--, X: cyano, Y: H,
[0227] m: 2, n: 4,
[0228] Total number of carbon atoms in R.sup.1, L.sup.1, L.sup.2,
R.sup.3 and R.sup.4: 30
[0229] The azomethine compound of the formula (I) can be
synthesized by referring to the method described in Japanese Patent
Provisional Publication No. 4(1992)-126772. The azomethine compound
can be synthesized by a reaction of an azole compound represented
by the formula (II) with a p-phenylenediamine compound represented
by the formula (III) under an oxidizing condition. 7
[0230] In the formulas (II) and (III), Z.sup.1, Z.sup.2, R.sup.1,
R.sup.2, X, Y, m, n and p are the same as those described above for
the formula (I); and R is a group eliminable in the reaction.
Examples of the eliminable groups (R) include hydrogen, a halogen
atom, a heterocyclic group and an aryloxy group.
[0231] Though a dye of the azomethine compound of the formula (I)
has excellent light resistance, an anti-fading agent can further
improve its light resistance. The anti-fading agent is described in
"Shikizai (written in Japanese)", 797, 70(1997). Particularly
preferred examples of the anti-fading agents are spirochroman and
spiroindane.
[0232] The azomethine compound of the formula (I) is preferably
used as a magenta dye, particularly an oily magenta ink suitably
used for ink-jet recording.
[0233] The oily magenta ink for ink-jet recording can be easily
prepared according to known publications (for example, Japanese
Patent Provisional Publication Nos. 3(1991)-231975,
11(1999)-158422, 11(1999)-172183).
[0234] Organic solvents employable for preparing the oily magenta
ink are hydrocarbons, alcohols, ketones, ethers, esters, nitriles,
amides, sulfoxides and sulfones. Esters and ketones are
particularly preferred.
[0235] Examples of the hydrocarbons include petroleum ether,
petroleum benzine, tetralin, decalin, 1-amylbenzene and
methylnaphthalene.
[0236] Examples of the alcohols include ethanol, pentanol,
heptanol, octanol, cyclohexanol, benzyl alcohol, phenyl-ethyl
alcohol, phenylpropyl alcohol, anise alcohol, ethylene glycol
monoethyl ether, ethylene glycol monophenyl ether, diethylene
glycol monoethyl ether, diethylene glycol monobutyl ether,
propylene glycol monoethyl ether, propylene glycol monophenyl
ether, dipropylene glycol monomethyl ether, dipropylene glycol
monoethyl ether and tripropylene glycol monoethyl ether.
[0237] Examples of the ketones include methyl ethyl ketone, benzyl
methyl ketone, diacetone alcohol and cyclohexanone.
[0238] Examples of the ethers include butyl phenyl ether, benzyl
ethyl ether and hexyl ether.
[0239] Examples of the esters include ethyl acetate, amyl acetate,
benzyl acetate, phenylethyl acetate, phenoxyethyl acetate, ethyl
phenylacetate, benzyl propionate, ethyl benzoate, butyl benzoate,
ethyl laurate, butyl laurate, isopropyl myristate, isopropyl
palmitate, triethyl phosphate, tributyl phosphate, diethyl
phthalate, diethyl malonate, dipropyl malonate, diethyl
diethylmalonate, diethyl succinate, dibutyl succinate, diethyl
glutarate, diethyl adipate, dibutyl adipate, di(2-methoxyethyl)
adipate, diethyl sebacate, diethyl maleate, dibutyl maleate,
dioctyl maleate, diethyl fumarate, dioctyl fumarate, 3-hexenyl
cinnamate, ethylene glycol diacetate, ethylene glycol monoethyl
ether acetate and propylene glycol diacetate.
[0240] Examples of the nitriles include acetonitrile.
[0241] Examples of the amides include formamide,
N,N-di-methylformamide, N,N-dimethylacetamide,
N-methyl-2-pyrrolidone, N-vinyl-2-pyrrolidone and
N,N-diethyldodecaneamide.
[0242] Examples of the sulfoxides include dimethyl sulfoxide.
[0243] Examples of the sulfones include sulfolane.
[0244] Two or more organic solvents can be used in combination.
[0245] The oily magenta ink contains the azomethine compound
preferably in an amount of 0.2 to 20 wt. %, and more preferably in
an amount of 0.5 to 10 wt. %.
[0246] In addition to the azomethine compound and the organic
solvent, the ink can contain additives such as viscosity
controlling agent, surface tension controlling agent, specific
resistance controlling agent, film-formation controlling agent, UV
absorber, antioxidizing agent, anti-fading agent, anti-fungal
agent, rust inhibitor, dispersing agent and surface active
agent.
[0247] In ink-jet recording, droplets of the aforementioned oily
magenta ink (jet printing ink) are ejected to record an image on
recording paper (image-receiving material). In this case, the ink
preferably has a viscosity of not more than 40 cp and a surface
tension of 20 to 100 dyn/cm.
[0248] For forming a full-color image, oily inks of cyan and yellow
hues can be used together with the oily magenta ink. Further, an
oily ink of black hue can be used to control the tone of the
image.
[0249] As the recording paper (image-receiving material) for
ink-jet printing, coat paper is preferred from the viewpoints of
quality and durability of the image. Recording paper containing
polymer mordant is also preferred. The recording paper may contain
an inorganic pigment. The recording paper preferably comprises a
hydrophilic ink-receiving layer containing a hydrophilic binder.
The binder is preferably hardened with a curing agent. Further, the
recording paper may contain a matting agent. The layers
constituting the recording paper may contain a surface active agent
or an organic fluorine compound, and further may contain a polymer
latex, anti-fading agent and a fluorescent whitening dye.
[0250] Ink-jet recording is usually conducted in an on-demand
system or in a continuous system. As the head for ink-jet recording
(i.e., jet head), some types such as bubble jet type, thermal jet
type and ultrasonic type are known.
[0251] There are also some types of the ink-jet recording method.
For example, in one type, many small droplets of thin ink (which is
often referred to as "photo-ink") are jetted out. In another type,
two or more inks having the same hue but different concentrations
are used to improve image quality. Further, colorless and
transparent ink can be also usable.
EXAMPLE 1
[0252] 8
[0253] [Synthesis of azomethine compound (Ia-12)]
[0254] In 1,000 ml of ethyl acetate, 87.9 g of
2-[4-{3-(tetradecyloxycarbo- nyl)
propanoylamino}phenyl]-6-tert-butyl-7-chloropyrazolo[1,5-b][1,2,4]-tr-
iazole was dissolved. Independently, 400 ml of methanol and 100 g
of sodium carbonate were dissolved in 750 ml of water. The prepared
two solutions were mixed, and 39.1 g of
4-amino-N-butyl-N-(2-cyanoethyl) aniline was further added. The
obtained solution was dropwise added for 1.5 hour to a solution in
which 50.0 g of ammonium persulfate was dissolved in 300 ml of
water. The resulting solution was made to react for 1 hour. After
1,000 ml of ethyl acetate and 1,000 ml of water were added, the
organic phase was collected. The collected liquid was twice washed
with 1,500 ml of water, and the solvent was distilled off. To the
obtained oil, 300 ml of acetonitrile was added to precipitate a
crystalline product. The product was collected and air-dried, and
then recrystallized from 300 ml of methanol. Thus, 45 g of the
azomethine compound (Ia-12) was prepared. The yield was 40%, and
the melting point was 118-119.degree. C.
[0255] The starting material in the procedure, namely
2-[4-{3-(tetradecyloxycarbonyl)
propanoylamino}phenyl]-6-tert-butyl-7-
chloropyrazolo[1,5-b][1,2,4]-triazole, was before-hand synthesized
according to the method described in Japanese Patent Publication
No. 7(1995)-14941. Further,
4-amino-N-butyl-N-(2-cyanoethyl)-aniline was also beforehand
prepared from N-(2-cyanoethyl)-aniline in the known manner
(butylation, nitrosoation and reduction reactions).
EXAMPLE 2
[0256] 9
[0257] [Synthesis of azomethine compound (Ia-4)]
[0258] N-butylaniline and ethylacrylate were made to react to
prepare N-butyl-N-(2-ethoxycarbonylethyl)aniline, which was then
nitrosoated and reduced to synthesize
4-amino-N-butyl-N-(2-ethoxycarbonylethyl)aniline.
[0259] From the prepared compound, the azomethine compound (Ia-4)
was synthesized in the same manner as described in Example 1.
EXAMPLE 3
[0260] 10
[0261] [Synthesis of azomethine compounds]
[0262] The azomethine compounds (Ia-1), (Ia-6), (Ia-13), (Ia-14)
and (Ia-15) were synthesized in a similar manner to Example 1 or
2.
[0263] The melting points of the compounds (Ia-1) and (Ia-6) are
lower than room temperature (i.e., they are in the form of oily
liquid at room temperature). The melting point of the compound
(Ia-13) was 132-133.degree. C. , the melting point of the compound
(Ia-14) was 119-120.degree. C. , and the melting point of the
compound (Ia-15) was 118-120.degree. C.
EXAMPLE 4
[0264] [Preparation of oily magenta ink]
[0265] Each of the azomethine compounds (Ia-1), (Ia-6), (Ia-12),
(Ia-13), (Ia-14) and (Ia-15) prepared in Examples 1 and 3 was
dissolved in ethyl acetate, and thereby it was found that their
solubilities are more than 10 wt. %. Thus, oily magenta inks were
prepared.
[0266] Independently, each compound was also dissolved in methyl
ethyl ketone, and thereby it was found that their solubilities are
also more than 10 wt. %. Thus, other oily magenta inks were
prepared.
EXAMPLE 5
[0267] [Measurement of absorption maximum and molar extinction
co-efficient]
[0268] With respect to each of the ethyl acetate-base magenta inks
[ethyl acetate solutions of the compounds (Ia-1), (Ia-6), (Ia-12),
(Ia-13), (Ia-14) and (Ia-15)] prepared in Example 4, the absorption
maximum (.lambda.max) and molar extinction coefficient (.epsilon.)
were measured. The results are set forth in Table 1.
1 TABLE 1 Azomethine Absorption/maximum Molar extinction compound
(.lambda..sub.max) coefficient (.epsilon.) (Ia-1) 512 nm 5.0
.times. 10.sup.4 (Ia-6) 522 nm 5.2 .times. 10.sup.4 (Ia-12) 519 nm
4.8 .times. 10.sup.4 (Ia-13) 517 nm 4.6 .times. 10.sup.4 (Ia-14)
520 nm 4.8 .times. 10.sup.4 (Ia-15) 532 nm 4.9 .times. 10.sup.4
EXAMPLE 6
[0269] [Measurement of solubility]
[0270] With respect to each of the azomethine compounds (Ia-6),
(Ia-12) and (Ia-14), 600 mg of the compound was placed in a lidded
test tube. After 2 ml of ethyl acetate was added, the mixture was
treated with an ultrasonic cleaner for 30 minutes. The resultant
liquid was heated and stirred at 65.degree. C. for 1 hour, and then
cooled to room temperature. After leaving the test tube in a
constant temperature bath at 25.degree. C. for 20 hours, solid
particles were filtered off with a micro filter having the pore
size of 0.2 .mu.m to prepare an oily magenta ink.
[0271] Each prepared ink was concentrated to measure the
solubility, but solid (crystallite) was not deposited. This
indicates that the solubility of each compound is more than 30 wt.
%.
COMPARISON EXAMPLE 1
[0272] [Measurement of solubility]
[0273] With respect to each of the following azomethine compounds
(X-1), (X-2), (X-3) and (X-4), 30 mg of the compound was placed in
a lidded test tube. After 2 ml of ethyl acetate was added, the
mixture was treated with an ultrasonic cleaner for 30 minutes. The
resultant liquid was heated and stirred at 65.degree. C. for 1
hour, and then cooled to room temperature. After leaving the test
tube in a constant temperature bath at 25.degree. C. for 20 hours,
solid particles were filtered off with a micro filter having the
pore size of 0.2 .mu.m to prepare an oily magenta ink. 11
[0274] The azomethine compounds (X-1), (X-2), (X-3) and (X-4)
correspond to the compounds 1, 6, 16 and 18 in Japanese Patent
Provisional Publication No. 4(1992)-178646 (pages 11-13),
respectively.
[0275] Each prepared ink was concentrated to measure the
solubility. The results are set forth in Table 2.
COMPARISON EXAMPLE 2
[0276] [Measurement of absorption maximum]
[0277] With respect to each of the ethyl acetate-base magenta inks
[ethyl acetate solutions of the compounds (X-1), (X-2), (X-3) and
(X-4)] prepared in Comparison Example 1, the absorption maximum
(.lambda.max) was measured. The results are set forth in Table
2.
2 TABLE 2 Azomethine Absorption maximum compound (.lambda..sub.max)
Solubility (Ia-6) 522 nm 30.2 wt. % or more (Ia-12) 519 nm 30.1 wt.
% or more (Ia-14) 520 nm 30.1 wt. % or more (X-1) 504 nm 0.18 wt. %
(X-2) 520 nm 0.29 wt. % (X-3) 511 nm 1.72 wt. % (X-4) 536 nm 0.63
wt. %
* * * * *