Metallized bisazo dyes, their preparation and use

Details Metallized bisazo dyes, their preparation and use Metallized bisazo dyes, their preparation and use

1999-08-18

2001-10-16

Klemanski, Helene (Department: 1755)

Compositions: coating or plastic

Coating or plastic compositions

Marking

C106S031480, C106S031500, C534S602000, C534S701000, C534S719000

Reexamination Certificate

active

06302949

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to novel metallized black bisazo dyes useful in the dyeing of natural and synthetic materials or modified natural or synthetic materials, for example cellulose, pulp, paper, coated paper, cotton, wool, silk, leather, polyamides, polyesters, plastics, resins, varnishes, inks or in manufacturing of toners or pigments of the lake type. More particularly, the present invention relates to new, lightfast metallized black bisazo dyes and recording liquids containing these dyes for ink jet printing processes.
BACKGROUND OF THE INVENTION
Ink jet printing processes generally are of two types: continuous stream and drop-on-demand. In continuous stream ink jet printing systems, ink is emitted in a continuous stream under pressure through an orifice or nozzle. The stream is perturbed, causing it to break up into droplets at a fixed distance from the nozzle. At the break-up point, the droplets are charged in accordance with digital data signals and passed through an electrostatic field which adjusts the trajectory of each droplet in order to direct it to a specific location on a recording medium or to a waste ink collecting recipient. In the non-continuous process, or the so called “drop-on-demand” systems, a droplet is expelled from a nozzle to a position on a recording medium in accordance with digital data signals. A droplet is not formed or expelled unless it is to be placed on the recording medium.
The most important part of an ink used in ink jet printing are the dyes. Although a number of dyes have been proposed none has been produced which meets all the requirements of a modern printing process.
C.I. “Food Black 2” (formula I) and dyes having similar structures have been mentioned as black dyes for ink jet printing inks in JP Patent Application 59-093'766. These dyes, however have a somewhat bluish hue and give images with poor light fastness.
Reactive black dyes have also been proposed for ink jet printing for example in the Patent Application EP 0,693,537. However, inks containing dyes with incorporated reactive groups deteriorate the storage stability of the inks and due to their potential health risk they are not particularly suitable for handling in a non chemical environment.
Black type recording liquids using “Pacified Reactive Black Dyes” are described in U.S. Pat. No. 5,725,641. It relates to ink compositions comprising the metallized azo dye “Reactive Black 31” in either or both of its hydrolysed forms according to general formula (II)
where X is CH
2
CH
2
OH and/or CH═CH
2
.
These inks are claimed to be lightfast and to possess reliable ink jet pen performance.
The pacification process is accomplished by making an aqueous solution of “Reactive Black 31”. The aqueous solution is heated to 60° C. and the dye is hydrolysed by addition of sodium hydroxide in amounts sufficient to bring the pH of the solution to a range of about 8 to about 12. After the completion of the hydrolysis the pH of the solution is lowered to about 7 with hydrochloric acid. The recording liquids in U.S. Pat. No. 5,725,641 are required to contain less than 1 wt % of sulphate ions, preferably less than about 1000 parts per million. Thus the sulphate ions generated during the hydrolysis reaction and the chloride and sodium ions added during the process have to be removed in an additional purification step. Further, to compensate the reduced water solubility of the dyes of general formula (II) compared to the initial “Reactive Black 31”, 10 to about 40 wt %, preferably 20 to about 25 wt %, of at least one organic solvent are required to provide inks with the claimed performance. Furthermore, on exposure to light, images on a range of recording materials suffer from colour shifts when printed with ink jet inks containing “Reactive Black 31” or “Pacified Reactive Black 31”.
In Patent Application EP 0,662,499 ink jet inks using either metallized or non-metallized azo dyes are disclosed. Dyes preferentially used for black recording liquids were “Acid Black 51” (Formula III) and/or “Reactive Black 1” (Formula IV).
However, both of these black metallized azo dyes are based on metal ions, such as chromium ions, which are presently regarded by the United States Regulatory Authorities as priority pollutants.
In Patent Application DE 3,236,238 1:1 metallized bisazo dyes of general formula (V) are claimed as being useful for dyeing and printing of cellulose containing materials in blue shades
wherein D is substituted phenyl or naphthyl; R
1
is hydrogen, alkyl or alkoxy with 1 to 4 C atoms, NHCONH
2
or NHCOR
3
where R
3
is alkyl with 1 to 4 C atoms; R
2
is hydrogen or unsubstituted or substituted phenyl and Met is copper or nickel.
In Patent Application EP 0,632,105 metallized bisazo dyes of general formula (VI) are claimed as blue dyes for dying paper making material and cellulose fibres
wherein A represents phenyl or naphthyl having one or more sulpho groups; m is 0 or 1 with the proviso that m is 1 when n is 0 and m is 0 when n is 2.
In Patent Application EP 0,593,324 metallized bisazo dyes of general structure (VII) are claimed and polarising films having said dyes incorporated therein are described
wherein Met is copper, nickel, zinc or iron; Q is a substituted or unsubstituted phenyl or naphthyl group and Z is hydrogen, lower alkyl, lower alkoxy, sulpho, and substituted or unsubstituted amino. The hue of all these metallized dyes is greenish blue to blue.
In U.S. Pat. No. 5,639,809 polarising films containing metallized bisazo and trisazo dyes of general formula (VIII) have been described,
wherein Met represents copper, nickel, zinc or iron. However, all of the disclosed compounds are giving red to blue hues and yellow, red, orange or other dyes need to be added to provide a black colour.
Metallized azo dyes with structures mentioned above considered to be state of the art do not satisfy all the required demands when used in aqueous inks for ink jet printing.
Dyes used for such recording liquids have to be sufficiently soluble in water and typical ink liquids, should not show bronzing on recording materials (association of dye on the surface of the recording material), they have to be stable even when the recording liquid is stored for long periods of time, they need to provide printed images having high optical density, excellent water fastness and excellent light fastness. Various types of compositions have been proposed as inks for use in ink jet printing. Typical inks are composed of various types of dyes, water, organic solvents, cosolvents and other additives.
In particular the inks have to meet the following criteria:
(1) The ink gives high quality images on any type of recording medium.
(2) The ink gives printed images exhibiting excellent water fastness.
(3) The ink gives printed images exhibiting excellent light fastness.
(4) The ink does not clog jetting nozzles even when these are kept uncapped while recording is suspended.
(5) The ink is quickly fixed onto recording media without bronzing and can not therefore be scrubbed off.
(6) The ink can be stored for a long period of time without deterioration in its performance.
(7) Physical properties of the inks, such as viscosity, conductivity and surface tension, are each within a defined range.
(8) The recording liquid has to be safe, non toxic and not flammable.
DESCRIPTION OF THE INVENTION
The present invention relates to novel metallized bisazo dyes useful in black dyeing of natural and synthetic materials or modified natural or synthetic materials, for example cellulose, pulp, paper, coated paper, cotton, wool, silk, leather, polyamides. polyesters, plastics, resins, varnishes or for manufacturing of inks or toners or pigments of the lake type.
More particularly, this invention relates to novel metallized bisazo dyes suitable for inks for ink jet printing showing high solubility, providing reliable ink jet pen performance and forming images having neutral black colour, high optical density, excellent water fastness, excellent light stability and no or little association of d

Affiliated with

Also associated with

Rating

Metallized bisazo dyes, their preparation and use does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Metallized bisazo dyes, their preparation and use, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Metallized bisazo dyes, their preparation and use will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2605972