JPS6081249A - Disazo based compound - Google Patents

Abstract

NEW MATERIAL:A compound of formula I (Q is -SO3M, substituted phenylene or naphthylene; R is H, lower alkyl, lower alkoxyl, lower acylamino, nitro or halogen; R<1> is -SO3M or -COOM-substituted phenyl, lower alkylaminocarbonyl lower alkyl; R<2> is H, -COOM-substituted lower alkyl, etc.; M is alkali metal, ammonium or amine; n is 0 or 1). EXAMPLE:A compound of formula II. 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 III is diazotized with sodium nitrite, etc. in a mineral acid, e.g. hydrochloric acid, and then coupled with an amine of formula IV (Q1 is phenylene or naphthylene) to give a monoazo compound of formula V, which is then diazotized and coupled with a naphthol of formula VI.

Description

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

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

For the above applications, especially ink for inkjet printers (
(hereinafter referred to as the recording liquid) are as follows: 6) Long-term storage stability of the recording liquid (b) Ejection stability (c) Ejection response) Quality of the recorded image (e) Fixability to the recording material, etc. There are some excellent things.

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

An object of the present invention is to provide a water-soluble disazo compound.

That is, 5 the present invention is based on the following general formula CI) (wherein, R represents a phenylene group or a naphthylene group substituted with a group of Q-803M, and R is a hydrogen atom, a lower alkyl group, a lower alkoxy group, a lower aciphenyl group, -0
Represents a lower alkyl group or lower alkylaminocarbonyl lower alkyl group substituted with a group of 00M, R2 represents a hydrogen atom, represents a lower alkyl group or lower alkylaminocarbonyl lower alkyl group substituted with a group of -000M, and M represents an alkali group. The gist thereof is a disazo compound represented by a metal, ammonium, or amine, and n represents O or l.

The present invention will be explained in more detail below.

In the above general formula (1), the lower alkyl group is 01
-C4 alkyl groups are mentioned, preferably methyl, ethyl, and propyl groups. Examples of the lower alkoxy group include 01-C4 alkoxy groups, preferably methoxy and ethoxy groups. Examples of the lower acylamino group include an acetylamino group and a globionylamino group. Examples of chlorine atoms include chlorine atoms and bromine atoms. Examples of alkali metals include Li, Na, and K.
can be mentioned. Examples of amines include triethanolamine.

Specific examples of the compound of the present invention represented by the general formula (1) include those shown in Table 1 above.

Table 1 Compounds of the present invention are described, for example, in "Theoretical Manufacturing Dye Chemistry" by Yutaka Hoso, published by Gihodo (published on July ts, 1968), No.
Page s, line 2r to voice 5g, line 1j, or “New Stock Price Chemistry” by Yutaka Hosoda, published by Gihodo (December 21, 1949)
It can be obtained by the following method according to the following publication, page 3, page 7, line 27 to page 32r, line 1, etc.

After diazotizing amines represented by the following general formula (It) [in which R is the same as defined above] using sodium nitrite in a mineral acid such as hydrochloric acid or sulfuric acid, the following general formula (III) 03H Ql -NH2・・・・・・・・・・・・ (III)
(In the formula, Q1 represents a phenylene group or a naphthylene group.) By coupling with an amine represented by It will be done.

The obtained monoazo compound is diazotized using sodium nitrite in a mineral acid such as hydrochloric acid or sulfuric acid, and then a naphthol represented by the following general formula (VJ [wherein R1, H2 and n are the same as defined above]) The disazo compound of the present invention can be obtained by coupling with .

The compound of the present invention has properties such as good light resistance, water resistance, heat resistance, and long-term storage stability, and is therefore useful in the field of electronic information materials, particularly as a pigment for ink for inkjet printers.

EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to examples, but the present invention is not limited to the following examples.

(1) Production of first diazo liquid Sulfanilic acid/7. j! -wo3% salt e3'lt
Add to the side and stir for 3 hours to form a homogeneous slurry. Ice λooy- was added to this and the mixture was cooled to 3c. An aqueous solution of 7.3z of sodium nitrite dissolved in 73 cc of water was added to this slurry. Next, the mixture was stirred at 3C for 1 to 1 hour to effect diazotization, and then sulfamic acid 31 was added to eliminate the remaining sodium nitrite to obtain a first diazo solution.

(2) Production of λth diazo liquid/ 2.2.3y- of 7-crepeic acid was added to water ttsocc, stirred for 1 hour to make a uniform slurry, and ice 30θ1 was added thereto and cooled to 3C. . The first diazo solution obtained in fl) above was added to this slurry, and then 2z%
After adjusting the pH to 2 by adding 10 cc of sodium chloride, stirring was carried out for 16 hours while maintaining the temperature at 3 C% pH 2, salting out was carried out by adding 2001 common salt. After filtering the precipitated monoazo compound, 10% saline SO
It was washed with O flash and dried to obtain 3g, tf of a monoazo compound. Obtained monoazo compound 20.4
1'i/- was added to 10 ml of t% hydrochloric acid and stirred for j hours to form a homogeneous slurry, which was then cooled to 3C by adding 300 f of ice. In this slurry,
An aqueous solution of sodium nitrite 3J1 was added to 31 cc of water. Next, the mixture was diazotized by stirring at 3C for an hour, and then sulfamic acid/1 was added to eliminate the remaining sodium nitrite to obtain a λth diazo solution.

(3) Campling N-β-carboxyethyl gamma acid/j, A was added to water ≠ 60 cc, and then 20 cc of Jj% caustic soda water was added to adjust the pI (pI). After stirring at the same temperature and pH for j hours while maintaining the pH at r~70% and temperature λ~tC, salting out was performed by adding common salt xsoP.The precipitated compound was treated with P. Thereafter, the mixture was washed with 300 cc of 10% saline, wet caked for λ10, and dried to obtain the target compounds)♂ and Go1. Yield is 7ff
, , It%.

The results of elemental analysis were as follows.

[Study of Preparation and Characteristics of Recording Liquid J Ion-exchanged water 7/ii parts Diethylene glycol, 2-fMJlf3A/ compound μ parts by weight Needle 100 M parts The above components were thoroughly mixed and dissolved in a container, and the pore size was 1μ. After pressure filtration with a Teflon filter, deaeration was performed using a vacuum pump to obtain a recording liquid. Using the obtained recording liquid, we conducted the following studies (a) to (e) using an on-demand recording head (having an ejection orifice diameter jOμ) that ejects the recording liquid using a piezo vibrator. Good results were obtained in all cases.

(b) Long-term storage stability of the recording liquid: Even after storing the recording liquid in a sealed glass container at -3θC and 6OC for 6 months, no precipitation of insoluble matter was observed, and no changes were observed in the physical properties or color tone of the liquid. There wasn't.

(b) Ejection stability: Continuous ejection was performed for 24 hours in the atmospheres of room temperature, JP, and ≠OC, and stable high-quality recordings were obtained from beginning to end under all conditions.

(c) Ejection responsiveness: Intermittent ejection every 2 seconds and ejection after being left for 2 months were investigated, and in both cases stable and uniform recording was achieved without clogging at the orifice tip.

(d) Quality of recorded images: The recorded images had high density and were clear. In addition, the rate of decrease in concentration after three months of exposure to indoor light was less than 7%, and when immersed in water for 1 minute,
There was very little blurring in the image.

(E) Fixing properties for various recording materials: It showed excellent fixing properties compared to the above.

Table 2 (1) Preparation of first diazo liquid Sulfanilic acid/7.3f/- was added to tri-hydrochloric acid 3≠tCC and stirred for 3 hours to form a uniform slurry. Add 2 ice cubes to this
0Of- was added and cooled to 3c. In this slurry,
An aqueous solution of 7.37 ml of sodium nitrite dissolved in 7 ml of water was added. Next, while maintaining the temperature at 3C, the mixture was stirred for 1 hour to effect diazotization, and then sulfamic acid 31 was added to eliminate the remaining sodium nitrite to obtain a first diazo solution.

(2) Production of second diazo liquid/2.2.3 F of 7-crepe acid to 41 F of water! Oc
After stirring for 2 hours to obtain a uniform slurry, ice 3001 was added to the slurry and the slurry was cooled to 3c.

The first diazo solution obtained in (1) above was added to this slurry, and then 10 cc of 2J% hydric soda was stirred between the legs to perform coupling. . After filtering the precipitated monoazo compound, it was washed with 300 cc of 10% saline and dried to obtain monoazo compound 3≠,
I got tl. Obtained monoazo compound, 20. Hiro? of!
After adding 10 cC of dihydrochloric acid and stirring for 5 hours to make a homogeneous slurry, 300? of ice was added and cooled to 3C.Into this slurry, an aqueous solution of 3.19 ml of sodium nitrite dissolved in 31 cc of water was added. Then, after diazotization by stirring at 3C for v hours, sulfamic acid f1 was added to eliminate the remaining sodium nitrite to obtain a first cociazo solution.

(3) Campling metasulfophenyl gamma e/9. l#- water 6'0
After adding 0 cc of the solution, 20 cc of aqueous sodium hydroxide solution was added to adjust the pH to 0. Add 100f of ice to this 3
After brewing with C and keeping the pH at 1,101 temperature λ~jC, the first cociazo liquid obtained in (2) above, ice, 2009- and 2! Chika Soda 3! Coupling was performed by adding flashes alternately. After stirring at the same temperature and pH for 5 hours,
00f was added to perform salting out. After filtering out the precipitated compound, it was washed with 300 cc of 10φ saline solution, and the wet cake was λrOf 0.2 parts.

The results of elemental analysis were as follows.

Further, according to the method of Example 1, a recording liquid was obtained using the &co compound. The obtained recording liquid has the above characteristics (a) to (,
Excellent at j9.

(1) Preparation of first diazo liquid Ortanilic acid/7.37 was added to 3≠l cc of trithihydrochloric acid and stirred for 3 hours to form a uniform slurry.

Ice 2009- was added to this to cool it to 3c.

In this slurry, add 7.3 cc of sodium nitrite to 73 cc of water.
An aqueous solution in which 1 was dissolved was added. Then, after diazotization by stirring for 1 hour while maintaining the temperature at 3C, sulfamic acid 31
was added to eliminate the remaining sodium nitrite to obtain a first diazo solution.

(2) Production of second diazo liquid l-aminonaphthalene-cosulfonic acid 2.2.3f
Water'I! After adding to Occ and stirring for 2 hours to make a uniform slurry, 300 fF of ice was added to the slurry and cooled to 3C. The first diazo liquid obtained in (1) above was added to this slurry, and then 25% sodium chloride/OCC was added to make a pl
(After adjusting the temperature to 3C and pH 2, stirring for 13 hours to perform compulsion, salt 2002 was added to perform salting out. After filtering the precipitated monoazo compound once, 300 cc of 70% saline solution was added. The obtained monoazo compound 20.1 was added to 10 cc of hydrochloric acid and stirred for 5 hours to form a homogeneous slurry. ? was added thereto and cooled to 3 C. An aqueous solution of 3.rg of sodium nitrite dissolved in 31 cc of water was added to this slurry.

Then, after diazotization by stirring for μ hours at 3C, sulfamic acid l? was added to eliminate the remaining sodium nitrite to obtain a first cociazo solution.

(3) Campling N-β-carboxyethylgamma ets, tl and 4L of water
2 after adding to A Occ! q6 caustic soda aqueous solution, 2
The pH was adjusted to - by adding 0 CC.

Add ice tooy to this and let it cool to 3C, then pH f ~ 10. temperature! Campling was carried out by alternately adding 33 cc of the cosciazo liquid obtained in the above (2), ice 2θoy-, and 25% strength soda while maintaining the temperature at ~jC.

After stirring at the same temperature and pH for 5 hours, common salt and 2KOf were added to salt out the dye. After filtering out the precipitated dye, 10
% saline solution 300 ee and wet cake 210f
I got it. This wet cake was desalinated and then dried to yield 2g of the target compound. I got f. The yield was 7.63 cm.

The results of elemental analysis were as follows.

Further, according to the method of Example 1, a recording liquid was obtained using the compound A/j. The obtained recording liquid has the above characteristics (a) to (
Excellent on the river.

Sender: Mitsubishi Chemical Industries, Ltd. Representative Patent Attorney Hase - 1 other person

Claims (3)

[Claims] (1) General formula [I] (wherein, Q represents a Fe lower acylamino group substituted with a -803M group, a nitro group, or a rogen atom,
R1 represents a phenyl group substituted with a -803M group or a -C00M group, a lower alkyl group substituted with a -COoM group, or a lower alkylaminocarbonyl lower alkyl group, and R2 is a hydrogen atom or a -000M group. Substituted lower alkyl group or lower alkylaminocarbonyltin alkyl f: disazo compound represented by S-M represents alkali, ammonium or amines, n represents 0 or l) . (2) The disazo compound according to claim 1, wherein Q in the general formula (1) represents a naphthyl group. (3) The disazo compound according to claim 1, wherein M in the general formula CI) represents an alkali metal.