JPS60108470A - Naphthalene disazo compound - Google Patents

Abstract

NEW MATERIAL:The compound of formula I [X is 1-4C alkylcarbonylamino, allylcarbonylamino, 1-4C alkylsulfonylamino, allylsulfonylamino, (substituted) carbonamido, (substituted) sulfonamido, or -SO3M (M is alkali metal, ammonium, etc.); R<1> is H, 1-8C alkyl, 2-8C alkylcarbonyl, allylsulfonyl, etc.; R<2> is H or 1-8C alkyl; n is 0 or 1]. EXAMPLE:The compound of formula II. USE:A black pigment of a recording liquid in the electronic information material fields, e.g. for ink-jet printer. PREPARATION:For example, the amine of formula III is diazotized and coupled with the amine of formula IV. The obtained monoazo compound of formula V is diazotized, and coupled with the naphthol of formula VI to obtain the objective compound.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel 7talenedisazo compounds.

Specifically, the present invention relates to a novel naphthalene disazo compound that can be used as a black dye.

Conventionally, a compound represented by the following structural formula [Food Black-(0, Lλ 73!;)] is known as a naphthalene disazo compound, and this compound is used as a black dye.

An object of the present invention is to provide a novel naphthalene disazo compound that can be used as a black dye.

That is, the present invention is based on the following general formula [1] (wherein,
Represents a carbonamide group which may be substituted with an alkyl group having 1 to 1 carbon atoms, a sulfonamide group which may be substituted with an alkyl group having 1 to 1 carbon atoms, or a -8OaM group, and R' is hydrogen. Atom, alkyl group having 1-g carbon atoms.

an alkylcarbonyl group having co to g carbon atoms, an alkylsulfonyl group having g carbon atoms/g, an alkylcarbonyl group or -
It represents a group of OH or SOaM, and R2 represents a hydrogen atom or an alkyl group having carbon number/~g. However, X is 18O,
When M is a group, R1 and R2 do not have hydrogen atoms at the same time. M represents an alkali metal, ammonium, or amine, and the gist thereof is a naphthalene disazo compound represented by the following formula.

In the above formula [1], examples of the allyl group in X and R1 include phenyl group, paratolyl group, etc., and the alkali metal in M is Among the alkylcarbonylamino groups, an acetylamino group, a propionyl group, an allylcarbonylamino group, and particularly a benzoylamino group are preferred,
Furthermore, a group of -80,M is preferred. B+ is a hydrogen atom, an alkyl group with carbon number/-r, an alkylcarbonyl group with carbon number λ~g 'i'fCu '0HfS'OfM
A group of 3- is preferable, and M is preferably an alkali metal.

Specific examples of the compound of the present invention represented by the general formula [1] include those shown in Table 1 below.

4--101 The compounds of the present invention are described, for example, in "New Dye Chemistry" by Yutaka Hosoda (published on July 1st, 1920 by Guza Showa), Gihodo, page 397, column 1-
It can be obtained by the following method according to the description on page 39g, line 79, etc.

After diazotizing the amine represented by the following general formula [11] [same as in the formula or the above definition] using sodium nitrite or the like in a mineral acid such as hydrochloric acid or sulfuric acid, from the following general formula [1], A monoazo compound represented by the following general formula [IV] in which X is the same as defined above is obtained.

After diazotizing the obtained monoazo compound in a mineral acid such as hydrochloric acid or sulfuric acid using sodium nitrite or the like, a naphthol represented by the following general formula [V] [wherein H+, Rm and nFi are the same as defined above] By coupling with υ, the naphthalene disazo compound of the present invention can be obtained.

In recent years, water-soluble dyes have been increasingly used in the field of electronic materials such as information recording inks, especially inkjet printer inks, and color filters for solid-state image sensors. Preferred conditions for the recording ink (hereinafter referred to as recording liquid) include (a) long-term storage stability of the recording liquid (b) ejection stability (pi) ejection response), quality of the recorded image (pi), fixability to the recording material, etc. It can be mentioned that it is excellent in

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 condensation properties is an extremely important technique in this technical field.

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 recording liquids.

The present invention will now be explained in more detail with reference to Examples, but the present invention is not limited to the following Examples.

Example 1 [Synthesis of the compound of the first Omoteya 3] (1) Production of the first diazo liquid 3 g of sulfanilic acid/li, ? imrM3116m
1 and stirred for 3 hours to form a uniform slurry. Ice 20011 was added to this and the mixture was cooled to 3°C. An aqueous solution of 7.3 g of sodium nitrite dissolved in q3 ml of water was added to this slurry. Next, after diazotization by stirring at 3° C. for 1 hour, 3 g of sulfamic acid was added to eliminate remaining sodium nitrite to obtain a first diazo solution.

(2) Production of second diazo liquid/12.3 g of 7-crepeic acid was added to soml water and stirred for 2 hours to form a uniform slurry. To this, 30 g of ice, the first diluted solution obtained in (1) above, and 10 ml of λsqb hydric soda were added, and after stirring for a time of 0 to 3'C, the coupling was carried out. Salting out was performed by adding common salt -○olI.

After filtering out the precipitated monoazo compound, add IO saline!
Wash with r00ml and dry to obtain the following monoazo compound = 13-, ? 4(j Il was obtained. The obtained monoazo compound ko, 4Ig was added to 1110 m of j% hydrochloric acid and stirred for 3 hours to make a homogeneous slurry, then ice 3θol/ was added and heated to 3°C.
It was cooled to An aqueous solution of sodium nitrite J and gli dissolved in water 31; WL1 was added to this slurry. Next, after diazotization by stirring at 3° C. for a period of time, sulfamino acid/i was added to eliminate remaining sodium nitrite to obtain a cocyazotide solution.

(3) Coupling l-hydroxy-7-butylamino-naphthalene-3.
After adding 6-disulfonic acid/tlg 11 to water 4Itomt, ice gθog, the first cociazo liquid obtained in (2) above, and co! r Add the spicy soda rsmt and p
Hza~10. Coupling was carried out at a temperature of ~S°C. After stirring for 5 hours at the same temperature and pH of 15-14, 5 oy of common salt was added to perform salting out. The precipitated compound was filtered and washed with 3 oml of 10% brine to obtain a wet cake, 2/θg. After desalting this wet cake, it was dried to obtain 5 g of the target compound H 8 O, Na (3 pieces). The yield was 7 g, s.

The results of elemental analysis were as follows.

Example 2 [Synthesis of dye shown in Table 1 S] (1) Production of first diazo solution Using dami-acetanilide/in place of sulfurinyl acid 1. A first diazo liquid was obtained in accordance with the method (1) of Reference Example, except for using θI.

(2) Mc! (A diazo solution (first) of the following monoazo compound was obtained according to the method of (2) of Reference Example, except that the first diazo solution obtained in step 11 was used.

(3) 3 g of the target dye 0sNa was obtained according to the method of (3) of Reference Example 1, except that coupling l-hydroxy-7-amino-naphthalene-3,6-disulfone rIIlb, 0& was used. . The yield was gs, 096.

The results of elemental analysis were as follows.

Example 3 [Synthesis of the first Omoteya Otsu dye] Using the first diazo liquid obtained by the methods (1) and (2) of Reference Example, g-hydroxy-6-sulfonic acid-1-naphthyl Aminomethanesulfonic acid H/i? The desired dye 17-O-t, All was obtained according to the method of (3) of Reference Example 1, except that , 9 was used. The yield was 7 g, excellent.

The results of elemental analysis were as follows.

Example G [Study of preparation and properties of recording liquid] Diethylene glycol CoSO Compounds in Table 1 A/Da9 Shochu 1001 The above components were thoroughly mixed and dissolved in a container, and the mixture was pressurized using a Teflon filter with a pore size of lμ. After 18 hours, degassing was performed using a vacuum pump to obtain a recording liquid. Using the obtained recording liquid, an on-demand recording head (discharge orifice diameter SOμ piezo vibrator drive voltage tOV, frequency Q KH) ejects the recording liquid using a piezo vibrator.
When the following studies (a) to (i) were conducted using a recording device having 2), good results were obtained in all cases.

(b) Long-term storage stability of recording liquid: Even after recording liquid was sealed in a glass container and stored at -30°C and 60°C for 6 months, no precipitation of insoluble matter was observed, and there were no changes in the physical properties or color tone of the liquid. There was no.

(middle) Ejection stability: Continuous ejection was performed for −y hours in an atmosphere of room temperature, 3° C., and 0° C., and stable high-quality recordings were obtained from beginning to end under all conditions.

Ei Ejection Responsiveness: Intermittent ejection every 2 seconds and ejection after being left for a month were investigated, and in both cases stable and uniform recording was achieved without clogging at the orifice tip.

b) Quality of recorded images: The recorded images had high density and clarity. Furthermore, the rate of decrease in density after three months of exposure to room light was less than 1 inch, and when immersed in water for a minute, there was very little blurring of the image.

(Middle) Fixability on various recording materials 2. Printing was performed on the recording materials listed in Table 1 below, and after /j seconds, the printed area was rubbed with a finger to determine the presence or absence of image shift and bleeding. It exhibited excellent fixing properties with no bleeding.

'Also, according to the method of Example G, a recording liquid was prepared using the compounds listed in Table 7, and the properties of the obtained recording liquid were investigated, but none of the above properties (a) to (a) were observed. It was excellent.

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Claims (1)

[Claims] (1) The following general formula [I] OjM (wherein, - represents a carbonamide group optionally substituted with an alkyl group, a sulfonamido group optionally substituted with an alkyl group having 7 to 7 carbon atoms, or a 18o, M group, RI is a hydrogen atom , an alkyl group having 7 to g carbon atoms,
Alkylcarbonyl group with carbon atoms of -g, alkylsulfonyl group with carbon atoms of 7 to 1, allylsulfonyl group or -O
It represents a group of H, SO, or M, and R1 represents a hydrogen atom or an alkyl group having carbon number/~g. However, X is 18o, M
When RI and Ra do not have a hydrogen atom at the same time. M represents an alkali metal, ammonium or amine, and represents bnFiθ or l).