JPS6081250A - Monoazo based compound - Google Patents

Abstract

NEW MATERIAL:A compound of formula I [Q is formulas II-IV (R is H, lower alkyl, lower alkoxyl, lower acylamino, nitro, halogen, -COOM or -SO3M); M is alkali metal, ammonium or amine; X is acetyl, benzoyl, p-toluenesulfonyl or 4- chloro-6-hydroxy-1,3,5-triazin-2-yl]. EXAMPLE:A compound of formula V. USE:A dyestuff for ink used in ink jet printers having improved light, water and heat resistance and storage stability for a long period. PREPARATION:For example, an amine of formula VI (Q' is phenyl or naphthyl) is diazotized with sodium nitrite, etc. in a dilute mineral acid, e.g. hydrochloric acid, and then coupled with a naphthol of formula VII.

Description

[Detailed description of the invention] The present invention relates to novel monoazo compounds.

In recent years, water-soluble dyes have come into widespread use in the field of inks for information recording, especially inks for inkjet printers, adhesives, and color filters for solid-state operating devices.

For the above-mentioned uses, especially for Infusiera 1 printer ink (referred to as recording liquid), the preferable conditions are: The quality of recorded images (highlights include excellent fixability to recording materials, etc.).

Since the recording liquid used for such recording purposes is basically composed of a dye and its solvent, the above-mentioned characteristics are largely influenced by the inherent properties of the dye. Therefore, selecting a dye so that the recording liquid has the above-mentioned characteristics is an extremely important skill in this technical field.

The present invention is all about the above! 1) In order to obtain a recording liquid with excellent properties, one component of coloring the recording liquid is k) a water-soluble compound that can be used as a filter dye;
Even if it's IJ, it's so.

That is, the present invention provides the above 1. P Lj; formula []-) alkyl group, lower alkoxy group, lower acylamino group, nitro group,
Halogen atom, -000M group or -EI03M103M
group, )・1 is an alkali metal, ammonium or amine l
'J ''X memiwashi, X is acetyl group, benzoyl group,
A monoazo compound represented by 0 representing a para-toluenesulfonyl group or a goochloro-A-1 nitroxy-'+3+5F riazin-yl group? This is the summary.

Under J.S.O., non-invention will be explained in more detail.

In the above general formula [1,], the lower alkyl group is C
1" C4 alkyl group, preferably methyl group,
It is mediated by an ethyl group.

Examples of the lower alkoxy group include iic and -c4 alkoxy groups, and more preferably methquine and ethoxy groups.

Examples of the lower acylamino group include an acetylamino group and a propionylamino group.

Examples of the halogen atom include a Hanawa atom and a bromine atom.

Examples of the alkali metal include Ll and Na-K.

Examples of amines include triethanolamine.

In addition, in the case of -000M group substituted mackerel, when Q represents a benzyl group 7, the ortho position with respect to the azo group is preferable, and when Q represents a naphthyl group 'f/, the bery position with respect to the azo group is 1. Childish.

Specific examples of the "unexploded" compound represented by the general formula [I] include the following seven compounds shown in Table 1 below.

No. 1 Tatsui, 84, Ha, , Formula Maximum liquid absorption wavelength (water) (nm
] , cooNa no Nncoノ, , 6. ,
, .

6 days b'; OgAAL Evening: a HONHCOCH3, 2N light d 53 IJaO, S So3Na The compound of the present invention is, for example, "Theoretical Manufacturing Dye Chemistry" by Yutaka Hosoda, published by Gihodo [published on July 75, 1939] 5th tr
Page o, lines S to l1, or "New Dye Chemistry" by Yutaka Hosoda, published by Gihodo (Published on λ1, 1983), page q, lines 26 to 11. According to the description in the first column of page 2, etc., the following general formula [■] C! OOH MisoR-Q/-NH2・・・・・・・・・・・・・・・・・・
...[■] [In the formula, Q' represents a phenyl group or a naphthyl group, and R is the same as the above definition]. After diazotization using

It can be easily obtained by coupling with a naphthol represented by the general formula 1 below.

The uninvented compound has good light resistance, water resistance, heat resistance, and long-term storage stability, as well as clear color tone, so it is suitable for use in the electronic information system field, especially for inkjet printers. Useful as a coloring component in ink.

Although the present invention will be specifically explained below with reference to 811 non-explosion examples, the present invention is not limited to the following examples.

After adding 3.7 gf to CC with 3% hydrochloric acid, the mixture was stirred to make a -C uniform slurry. Ice and zoogon were added to this, and the mixture was cooled to 3°C. In this slurry, 73cc of water, q of sodium nitrite,
3iw? A water cup with a wide angle. Next, while maintaining the temperature at 3°C, W'i' was stirred for 1 hour to diazotize it, and then 3 g of sulfamine t'J was added to eliminate the remaining nitrous acid, and diada solution was added. Obtained. On the other hand, N-benzoyl H pH 2,39Y water was added to g s o cc, and then 2S% sodium chloride solution in water and 2 occ'ir were added.
H was adjusted to 9 to 1.1. Then, after adding ice goog and cooling to 3°C, the pH was adjusted to pH 2~-! t
While heating to °C, add 100 g of diazo solution, 100 g of ice and 1.25% hydric soda, 3 J Cc to 1 tsp.
So, I went to Coupling 2. After stirring at the same temperature for S hours, salt! io o g '6- was added to salt out the dye. After removing the precipitated dye, add 1.20% saline solution.
Washed with occ to obtain a wet cake.

This wet cake was desalinated and then rolled and combed to obtain 33.9 g of the desired dye. The yield was excellent, and the results of elemental analysis were as follows.

[Preparation of recording liquid and consideration of object]

Ion exchange water 7 parts by weight diethylene glycol Yu! i weight part A compound 'F//J da weight part All the above ingredients were thoroughly mixed and dissolved in a container, passed through a Teflon filter with a pore diameter of /μ, and then passed through a pressure IJ pressure filter using a vacuum pump. After degassing, records were obtained for 7 nights. The on-demand recording head (discharge orifice diameter: SO
μI Vieso oscillator 1 driving channel pressure 1. OV, frequency +4K
Using the recording apparatus V, which also has H2J, I performed the following hob adjustments (A) to (5) and obtained good results.

(Temporary long-term storagefL: The recording liquid was kept in a glass container and stored for 6 months at -30'C and θ℃.
) However, no precipitation of insoluble matter was observed, and there was no change in the physical properties or color tone of the liquid.

(b) Ejection Stability Continuous ejection was carried out for 2 V hours in two atmospheres: room temperature, S° C., and po° C. Under all conditions, stable high-quality recording was achieved from the beginning.

(c) Vomiting 12. Responsive knee per second ■] We investigated the lack of ejection and the ejection after leaving it for a month, and in both cases, there was no clogging at the orifice tip, and it was recorded stably and uniformly. Quality: Both parts recorded had 0 animals high<F+, near clear. If the density is less than 1% after being exposed to indoor light for 3 months, and if the image is immersed in water for a minute, the smearing will be extremely noticeable. Ivy.

(Each price was 8!'$), and the fixing properties for the recording opening were as follows.

Table 2 Antophunilic acid/3. '79 蓓・3% salt: 47g C
Power 11 to C, 1 line at 3 o'clock]・Stir to make a uniform slurry.

To this, 200 g of ice was removed to 3° C. by force. In this slurry 1)-73cc of water & 7.3g of τ sodium nitrite
7 molten angle'ζ water bath liquid fire 1. Next, while maintaining the temperature at 1-3°C, the mixture was stirred for 1 hour to diazotize the sulfamine ρ! ! 7 g'Y was added to eliminate the residual nitrous acid nose, and a diazo liquid was obtained. -10,000, N-acetyl H acid 3
Otsu, /g all water g left o (℃ 0 sword 0 rice 2s% chi'4
20QC of aqueous soda solution was added to adjust the pH to 9. Next, add ice g o o gY,=: and cool to 3°C.
After heating, p Hg ~/0, temperature ri, 2°~,! r I
While maintaining the CFC, add the diazo solution, ice, 2oog and 2
5% strength soda 35 cc 7. / Alternate Gτ shouted and went 11777 times. After stirring at the same temperature for 9 hours, sodium chloride was added and 5 dyes were separated. The precipitated dye was filtered and washed with -0% saline SθQ cc to obtain 3g09f of wet cake. This Uesotokegi 7 is desalinated and then dried to obtain the desired dye 11. g,
1I-9YKΣ again. The names were (Engke, Yu et al.) and the results of elemental analysis were as follows.

In addition, a recording liquid was prepared using compound A according to the method described in Example 1. The obtained recording liquid has the above characteristics (a)
~(He was really good.

Aniline-knot 5-dicarvone High, ig-requiring salt-reducing Jb 2 cc plus 1. ? A homogeneous slurry was obtained by stirring for 1+3 minutes. 200 g'fl of ice was added to A1 and cooled to 3°C. To this slurry was added an aqueous solution containing 73 cc of water [7.39 ml of nitrous chloride soda W4].

Then, it was held at 3℃(・fS time bond and diaso°
I took 3g of sulfamine in my mouth and finished it.
It was in. On the other hand, N-acetyl H eyes? Otsu, 7g begging water g!
;2 after adding 0CcIIl! Add 20 Ccyc of carbonated soda water and adjust the pH to 9. Next, add ice to 3℃ (tζ 1', remove 11 hours).
Buko G・, p) 1 g ~ / 0, Warm 1 skin f ~ 5' While keeping it at ~5'C, apply pressure alternately to mouth + J record / Azo 2 / night, ice ooog and 2 to 70Cc%' 0 and went to coupling 2. At the same temperature 5:00 1t-:1
After pressing thoroughly, SOθg of common salt was added to salt out the dye.

After filtering the precipitated pigment, add 20% food J Bonsui 5OOCC
The wet cake was washed with water to obtain 11309'' of wet cake.

This ・27 Esotho cake was desalinated and dried to obtain the desired dye f'411g, -? ,! 7 eye again. Yield is 7
In section s, the results of the element ν analysis are as follows.
Ivy.

In addition, a recording solution was prepared using Compound 7 according to the method described in UB'. The obtained recording liquid has the above characteristics (
I was superior to (a) to (e).

Applicant: Mitsubishi Chemical Corporation Agent Ben Okushi Hase - 1 other person

Claims (3)

[Claims] (1) Represented by the following general formula CI] R-kaikeCoo),', 7ij, P is water
/i', j, lower alkyl group, lower alkoxy group, lower acylamino group, nitro group, halogen atom, -000
1\4 group or -8o3M group,) A is Arnol
IJ Gold Metal Anne7ium Mataji L Puminzu 17 Representation, X
is a monoazo compound represented by an acetyl group, a benzoyl group, a para-toluenesulfonyl group, or a darkchloro-ethyl-hydroxy-/, 3.3) a riazine-niyl group. (2) A monoazo compound according to claim 1, wherein in the general formula [I'l, X represents an acetyl group or a benzoyl group. (3) In the general formula [■], M is an alkali metal 7
11 yen, a monoazo compound of claim 1.