Compositions: coating or plastic – Coating or plastic compositions – Marking
Reexamination Certificate
1999-09-30
2001-03-13
Klemanski, Helene (Department: 1755)
Compositions: coating or plastic
Coating or plastic compositions
Marking
C106S031500, C106S031510
Reexamination Certificate
active
06200370
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a jet printing ink and an ink image-forming method using an ink jet printer.
BACKGROUND OF THE INVENTION
An ink-jet recording method has been developed and widely used because it has various merits. For example, materials for the method are available at a low cost, and high speed recording can be accomplished. Further, the method makes relatively low noise, and easily utilizable for full-color recording.
As the ink-jet recording method, three types are known. One is a method in which drops of ink are pressured to be ejected by means of a piezoelectric element. In another method, bubbles are formed in ink by heating so that the bubbles would push out drops of the ink. The other is a method in which drops of ink are sucked and ejected with electrostatic force. As the ink for the method (i.e., jet printing ink), various kinds of ink such as aqueous ink, oily ink, and solid (melting) ink have been used.
Dyes used for the ink must satisfy various conditions. For example, they must be highly soluble in a solvent, and they must have excellent hues. It is also necessary for the dyes to have high resistance against light, heat, air, water and chemicals. Further, they must be well fixed onto an image-receiving sheet without blotting. They are furthermore required to have long shelf lives, to have no toxicity, to have high purity, and to be available at a low cost. However, there are few dyes fully satisfying those conditions, and in particular it is desired to develop dyes having excellent magenta or cyan hue and high resistance to light.
Various dyes or pigments have been proposed and practically employed for ink-jet recording, but there is no dye (or pigment) fully satisfying all the aforementioned conditions. Conventional dyes or pigments (such as those having C.I. Number) cannot satisfy the conditions of both having high resistance and giving hues necessary for ink-jet recording. Japanese Patent Provisional Publications No. 61-36362 and No. H2-212566 disclose jet printing inks. Those inks give satisfying hues and have good durability, but the dyes disclosed in the Publications have not enough solubility in water to prepare an aqueous ink. Further, even if the dyes are used in aqueous ink, the prepared ink has poor resistance against heat and moisture.
SUMMARY OF THE INVENTION
It is an object of the present invention to provide an improved jet printing ink and an ink-jet recording method, in which the ink has excellent magenta or cyan hue, and gives an image having good durability.
There is provided by the invention a jet printing ink containing an azo dye represented by the following formula (I):
wherein X
1
is ═N— or ═CR
4
—; Y
1
is —N═ or —CR
5
═; Z
1
is —S—, —NR
6
— or —N═CR
7
— in which the right end of each group connects to Y
1
; the benzene ring A can have one or more substituents; each of R
1
, R
2
and R
6
independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, or an aryl group, said group possibly having one or more substituents; each of R
3
, R
4
, R
5
and R
7
independently represents a hydrogen atom, a halogen atom, cyano, hydroxyl, nitro, carboxyl, sulfo, an alkyl group, a cycloalkyl group, an aralkyl group, an aryl group, an alkoxy group, an alkylthio group, an acyl group, an acyloxy group, an alkoxycarbonyl group, an alkylamino group, an arylamino group, or an alkylsufonyl group; or a set of R
1
and R
2
, R
1
and the substituent of the benzene ring A, R
2
and the substituent of the benzene ring A, R
3
and R
4
, R
4
and R
5
, or R
5
and R
6
can be combined to form a heterocyclic or aromatic ring which can have one or more substituents; and at least one of R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
, the substituent of the benzene ring A, and the substituent of the formed heterocyclic or aromatic ring has at least one carboxyl or sulfo group.
In the invention, the azo dye is preferably represented by the following formula (II):
wherein X
2
is ═N— or ═CR
14
—; Z
2
is —S— or —NR
15
—; the benzene ring B can have a substituent; each of R
1
, R
12
and R
15
independently represents hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group or an aryl group, said group possibly having one or more substituents; each of R
13
and R
14
independently represents hydrogen atom, a halogen atom, cyano, hydroxyl, nitro, carboxyl, sulfo, an alkyl group, a cycloalkyl group, an aralkyl group, an aryl group, an alkoxy group, an alkylthio group, an acyl group, an acyloxy group, an alkoxycarbonyl group, an alkylamino group, an arylamino group or an alkylsulfonyl group; or a set of R
11
and R
12
, R
11
and the substituent of the benzene ring B, R
12
and the substituent of the benzene ring B, or R
13
and R
14
can be combined to form a heterocyclic or aromatic ring which can have a substituent; and at least one of the substituent of R
11
, R
12
, R
13
, R
14
, R
15
, the benzene ring B, and the substituent of the formed heterocyclic or aromatic ring has at least one carboxyl or sulfo group.
In the formula (I), at least one of R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
, the substituent of the benzene ring A, and the substituent of the formed heterocyclic or aromatic ring preferably has at least one sulfo group. Also preferred is that at least two of R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
, the substituent of the benzene ring A, and the substituent of the formed heterocyclic or aromatic ring has at least one sulfo or carboxyl group.
The ink of the invention preferably comprises an aqueous medium and the azo dye of the formula (I) that is dissolved in the aqueous medium, particularly, in an amount of 0.2 to 10 wt. %.
The invention further resides in a method of forming an ink image on a receiving sheet using an ink jet printer, which comprises jetting drops of an ink containing an azo dye of the aforementioned formula (I).
DETAILED DESCRIPTION OF THE INVENTION
The jet printing ink of the invention contains an azo dye of the aforementioned formula (I).
The benzene ring A in the formula (I) may have a substituent. Examples of the substituents include a halogen atom, cyano, hydroxyl, nitro, carboxyl, sulfo, amino, an alkyl group, a cycloalkyl group, an aralkyl group, an aryl group, a heterocyclic group, an alkylamino group, an alkoxy group, an aryloxy group, an amido group, an arylamide group, an ureido group, a sulfamoylamino group, an alkylthio group, an arylthio group, an alkoxycarbonylamino group, a sulfonamide group, a carbamoyl group, a sulfamoyl group, an alkylsulfonyl group, an arylsulfonyl group, an alkoxycarbonyl group, a heterocyclic oxy group, an azo group, an acyloxy group, a carbamoyloxy group, a silyloxy group, an aryloxycarbonyl group, an aryloxycarbonylamino group, an imido group, a heterocyclic thio group, a sulfinyl group, a phosphoryl group, and an acyl group. Preferred examples are a halogen atom, an alkyl group, an aryl group, cyano, an alkoxy group, an amido group, an ureido group, an alkoxycarbonylamino group, a sulfonamide group, a carbamoyl group, a sulfamoyl group, and an alkoxycarbonyl group. Particularly preferred examples are a halogen atom, an alkyl group, an alkoxy group, an amido group, an ureido group, and a sulfonamide group.
Examples of the halogen atoms include fluorine, chlorine and bromine.
The alkyl group preferably comprises 1 to 12 (more preferably 1 to 6, further preferably 1 to 3) carbon atoms, and may have a substituent. Examples of the substituents include hydroxyl, an alkoxy group, a halogen atom, sulfo, and carboxyl. Concrete examples of the alkyl group include methyl, ethyl, butyl, isopropyl, t-butyl, hydroxyethyl, methoxyethyl, cyanoethyl, trifluoromethyl, 3-sulfopropyl, and 4-sulfobutyl.
The cycloalkyl group preferably comprises 5 to 12 carbon atoms, such as cyclohexyl, and may have a substituent. Examples of the substituents include sulfo and carboxyl.
The aralkyl group preferably comprises 7 to 12 carbon atoms, such as benzyl and 2-phenethyl, and may have a substituent. Examples of the su
Fujiwara Toshiki
Kamio Takayoshi
Birch & Stewart Kolasch & Birch, LLP
Fuji Photo Film Co. , Ltd.
Klemanski Helene
LandOfFree
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