Azo pyridone colorants

Details Azo pyridone colorants Azo pyridone colorants

2002-06-27

2003-07-08

Powers, Fiona T. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Azo

C534S651000, C534S657000, C534S772000, C534SDIG002

Reexamination Certificate

active

06590082

ABSTRACT:

BACKGROUND OF THE INVENTION
The present invention is directed to colorant compounds. More specifically, the present invention is directed to azo pyridone colorant compounds particularly suitable for use in hot melt or phase change inks. One embodiment of the present invention is directed to compounds of the formula
wherein (A) R
3
is a linear alkyl group of the formula —(CH
2
)
c
CH
3
wherein c is an integer of 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9; (B) Z is (i) a hydrogen atom, (ii) a halogen atom, (iii) a nitro group, (iv) an alkyl group, (v) an aryl group, (vi) an arylalkyl group, (vii) an alkylaryl group, (viii) a group of the formula
wherein R
70
is an alkyl group, an aryl group, an arylalkyl group, an alkylaryl group, an alkoxy group, an aryloxy group, an arylalkyloxy group, an alkylaryloxy group, a polyalkyleneoxy group, a polyaryleneoxy group, a polyarylalkyleneoxy group, a polyalkylaryleneoxy group, a heterocyclic group, a silyl group, a siloxane group, a polysilylene group, or a polysiloxane group, (ix) a sulfonyl group of the formula —SO
2
R
80
wherein R
80
is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, an alkylaryl group, an alkoxy group, an aryloxy group, an arylalkyloxy group, an alkylaryloxy group, a polyalkyleneoxy group, a polyaryleneoxy group, a polyarylalkyleneoxy group, a polyalkylaryleneoxy group, a heterocyclic group, a silyl group, a siloxane group, a polysilylene group, or a polysiloxane group, or (x) a phosphoryl group of the formula —PO
3
R
90
wherein R
90
is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, an alkylaryl group, an alkoxy group, an aryloxy group, an arylalkyloxy group, an alkylaryloxy group, a polyalkyleneoxy group, a polyaryleneoxy group, a polyarylalkyleneoxy group, a polyalkylaryleneoxy group, a heterocyclic group, a silyl group, a siloxane group, a polysilylene group, or a polysiloxane group; and (C) either (1) X is an oxygen atom, R
1
is
wherein q is an integer of from about 10 to about 15, p is an integer of from 0 to about 3, and the sum of p+q=15,
or
—(CH
2
)
17
CH
3
and R
2
is
—CH
2
CH
3
,
—(CH
2
)
3
CH
3
,
—(CH
2
)
7
CH
3
,
—(CH
2
)
9
CH
3
,
—(CH
2
)
11
CH
3
,
—(CH
2
)
13
CH
3
,
—(CH
2
)
15
CH
3
,
—(CH
2
)
17
CH
3
,
wherein z is an integer of from about 34 to about 44, or (2) X is a —NH— group and (i) R
1
is
wherein q is an integer of from about 10 to about 15, p is an integer of from 0 to about 3, and the sum of p+q=15,
or
—(CH
2
)
17
CH
3
and R
2
is
—CH
2
CH
3
,
—(CH
2
)
3
CH
3
,
—(CH
2
)
7
CH
3
,
—(CH
2
)
9
CH
3
,
—(CH
2
)
11
CH
3
,
—(CH
2
)
13
CH
3
,
—(CH
2
)
15
CH
3
,
—(CH
2
)
17
CH
3
,
wherein z is an integer of from about 34 to about 44, or (ii) R
1
is
and R
2
is
—CH
2
CH
3
,
—CH
2
CH
2
CH
2
OH,
wherein z is an integer of from about 34 to about 44.
In general, phase change inks (sometimes referred to as “hot melt inks”) are in the solid phase at ambient temperature, but exist in the liquid phase at the elevated operating temperature of an ink jet printing device. At the jet operating temperature, droplets of liquid ink are ejected from the printing device and, when the ink droplets contact the surface of the recording substrate, either directly or via an intermediate heated transfer belt or drum, they quickly solidify to form a predetermined pattern of solidified ink drops. Phase change inks have also been used in other printing technologies, such as gravure printing, as disclosed in, for example, U.S. Pat. No. 5,496,879 and German Patent Publications DE 4205636AL and DE 4205713AL, the disclosures of each of which are totally incorporated herein by reference.
Phase change inks for color printing typically comprise a phase change ink carrier composition which is combined with a phase change ink compatible colorant. In a specific embodiment, a series of colored phase change inks can be formed by combining ink carrier compositions with compatible subtractive primary colorants. The subtractive primary colored phase change inks can comprise four component dyes, namely, cyan, magenta, yellow and black, although the inks are not limited to these four colors. These subtractive primary colored inks can be formed by using a single dye or a mixture of dyes. For example, magenta can be obtained by using a mixture of Solvent Red Dyes or a composite black can be obtained by mixing several dyes. U.S. Pat. Nos. 4,889,560, 4,889,761, and 5,372,852, the disclosures of each of which are totally incorporated herein by reference, teach that the subtractive primary colorants employed can comprise dyes from the classes of Color Index (C.I.) Solvent Dyes, Disperse Dyes, modified Acid and Direct Dyes, and Basic Dyes. The colorants can also include pigments, as disclosed in, for example, U.S. Pat. No. 5,221,335, the disclosure of which is totally incorporated herein by reference. U.S. Pat. No. 5,621,022, the disclosure of which is totally incorporated herein by reference, discloses the use of a specific class of polymeric dyes in phase change ink compositions.
Phase change inks have also been used for applications such as postal marking and industrial marking and labelling.
Phase change inks are desirable for ink jet printers because they remain in a solid phase at room temperature during shipping, long term storage, and the like. In addition, the problems associated with nozzle clogging as a result of ink evaporation with liquid ink jet inks are largely eliminated, thereby improving the reliability of the ink jet printing. Further, in phase change ink jet printers wherein the ink droplets are applied directly onto the final recording substrate (for example, paper, transparency material, and the like), the droplets solidify immediately upon contact with the substrate, so that migration of ink along the printing medium is prevented and dot quality is improved.
Compositions suitable for use as phase change ink carrier compositions are known. Some representative examples of references disclosing such materials include U.S. Pat. Nos. 3,653,932, 4,390,369, 4,484,948, 4,684,956, 4,851,045, 4,889,560, 5,006,170, 5,151,120, 5,372,852, 5,496,879, European Patent Publication 0187352, European Patent Publication 0206286, German Patent Publication DE 4205636AL, German Patent Publication DE 4205713AL, and PCT Patent Application WO 94/04619, the disclosures of each of which are totally incorporated herein by reference. Suitable carrier materials can include paraffins, microcrystalline waxes, polyethylene waxes, ester waxes, fatty acids and other waxy materials, fatty amide containing materials, sulfonamide materials, resinous materials made from different natural sources (tall oil rosins and rosin esters, for example), and many synthetic resins, oligomers, polymers, and copolymers.
European Patent Publication 1 125 990 A1 and PCT Patent Publication WO 01/09256 A1, the disclosures of each of which are totally incorporated herein by reference, discloses an aqueous ink for ink jet recording which contains at least a water-insoluble coloring matter, water, and a resin as main components and which takes the form of an emulsion, which is characterized by containing at least one yellow hue coloring matter selected from the group consisting of a quinophthalone compound represented by the formula (1)
wherein each of R
1
to R
3
independently represents a hydrogen atom, an unsubstituted or substituted alkyl group, —CONR
4
R
5
, or —COOR
6
(in which each of R
4
to R
6
independently represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted aryl group) and all of R
1
to R
3
are not a hydrogen atom at the same time, and a pyridone azo compound represented by the formula (2)
wherein each of R
7
to R
11
independently represents a hydrogen atom, a halogen atom, an unsubstituted or substituted alkyl group, an aralkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, a hydroxyl group, —NR
14
R
15
(in which R
14
and R
15
independently rep

Affiliated with

Also associated with

Rating

Azo pyridone colorants does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Azo pyridone colorants, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Azo pyridone colorants will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3065134