JPH06104776B2 - Monoazo compound and monoazo dye - Google Patents

Description

TECHNICAL FIELD The present invention relates to a monoazo compound having a specific structure. Furthermore,
Particularly, it relates to a monoazo dye having excellent wet fastness after post-processing.

(Prior Art) Recently, various post-treatments such as water-repellent treatment, texture improving treatment, antistatic treatment, and sanitary treatment have been performed on polyester cloth.

Since the post-processing as described above is carried out at a high temperature, the dye bleeds from the already dyed fiber or the like, which causes a problem that various fastnesses of the fiber or the like, particularly wet fastness, are deteriorated.

(Problems to be Solved by the Invention) An object of the present invention is to provide a novel monoazo compound. Furthermore, synthetic fibers, especially polyester fibers,
Or it is a monoazo dye capable of dyeing cloth or the like produced from these in an orange or blue color, and bleeding does not occur even when the obtained dyed cloth or the like is post-processed, and therefore, wash fastness and alkali sweat fastness The object is to provide a monoazo dye having excellent wet fastness such as water fastness.

(Means for Solving Problems) The present invention provides the following general formula [I]. (In the formula, X is hydrogen atom, chlorine atom, bromine atom, nitro group, cyano group, C _1-4 alkyl group, C _1-4 alkoxy group, CF
₃ groups, SO ₂ R ″ groups or COR groups, wherein R and R ′ are each independently a hydrogen atom; C _1-8 alkyl group; C _1-8 alkoxy group, cyano group, chlorine atom, acyloxy group, C _{1 -8} alkoxycarbonyl group, C _1-8 alkoxycarbonyloxy group, benzyloxycarbonyl group, phenoxyethyloxycarbonyl group, benzyloxycarbonyloxy group, allyloxy group or C _1-4 which may be substituted with aryl group An alkyl group; an allyl group; or a phenyl group, R ″ represents a C _1-8 alkyl group or a phenyl group, R represents a hydrogen atom or a C _1-8 alkyl group, and Y represents a hydrogen atom, a chlorine atom or C _1-4 represents a monoazo compound represented by (alkoxy group)).

In the above general formula [I], the alkyl group or alkoxy group represented by X, R, R'and Y may be linear or branched.

Particularly preferred dyes in the present invention include, for example, in the general formula [I] shown above, X represents a nitro group, a methyl group, a chlorine atom or a hydrogen atom, and Y represents a hydrogen atom,
And monoazo compounds in which R and _{R'represent a} C _1-8 alkyl group, a C _1-8 alkoxyethyl group, an allyl group or an aralkyl group.

The monoazo compound represented by the above general formula [I] is, for example, the following general formula [II] (Wherein X, Y, R and R ′ are the same as defined above,
Z represents a chlorine atom or a bromine atom), a monoazo compound represented by the following formula is synthesized in advance by a conventional method from each corresponding diazo component and coupling component, and then the monoazo compound is added in a polar solvent such as dimethylformamide. It can be easily produced by cyanating with a cyanating agent such as a theoretical amount of sodium cyanide or cuprous cyanide.

Fibers that can be dyed with the azo dye of the present invention include polyethylene terephthalate, terephthalic acid and 1,4-bis-
Examples thereof include polyester fibers composed of a polycondensation product with (hydroxymethyl) cyclohexane, or a blended product or a blended product of the above polyester fibers with a natural fiber such as cotton, silk or wool.

In order to dye polyester fibers with the dye of the present invention, since the dye represented by the general formula [I] shown above is insoluble or sparingly soluble in water, naphthalenesulfonic acid and formaldehyde are used as dispersants by a conventional method. Dyeing or printing may be carried out by preparing a dyeing bath or a printing paste dispersed in an aqueous medium using a condensate, a higher alcohol sulfate, a higher alkylbenzene sulfonate or the like. For example, in the case of dip dyeing, polyester fibers or a blended product thereof can be dyed with excellent fastness by applying an ordinary dyeing treatment method such as a high temperature dyeing method, a carrier dyeing method and a thermosol dyeing method. At that time, if desired, if an acidic substance such as formic acid, acetic acid, phosphoric acid, or ammonium sulfate is added to the dyeing bath, further favorable results can be obtained.

The monoazo dye of the present invention represented by the general formula [I] shown above may be used in combination with a dye of the same system or a dye of another system, and among these, the monoazo dye of the present invention represented by the general formula [I] shown above is used. Good results such as improved dyeability may be obtained by mixing the dyes with each other.

(Examples) Next, the present invention will be described more specifically by way of examples, but the present invention is not limited to the following examples.

Example 1 The following structural formula 0.5 g of monoazo dye represented by
A dyebath was prepared by dispersing 3 g of water containing 1 g of formaldehyde condensate and 2 g of higher alcohol sulfate ester. 100g of polyester fiber is dipped in this dyeing bath and 60
After dyeing for a minute, soaping, washing with water and drying were carried out, and a clear red dyed fabric was obtained. The obtained dyed cloth had good fastness to light, fastness to sublimation and fastness to water, and temperature stability and pH stability during dyeing of the above dye.

The wet fastness (fastness to washing, fastness to alkaline sweat and fastness to water) after subjecting the obtained dyed fabric to a further polyurethane treatment (handling treatment) was determined according to the following method, and the results are shown below. The results are shown in Table 1.

(1) Polyurethane processing method After soaking in a 1% solution of Hydran F-24K, cure at 160 ° C for 2 minutes.

(2) Washing fastness A multi-fiber is attached to a dyed fabric with a polyurethane finish, and a washing test is performed according to AATCC Wash IIA.
The contamination of the nylon fiber of the multifiber was judged on a gray scale.

(3) Alkaline sweat fastness Polyurethane-processed dyed fabric conforms to JIS L-0848A method, but the attached fabric was tested using nylon cloth and silk cloth, and the degree of contamination of silk cloth was grayscale. It was judged.

(4) Water fastness Dyeing cloth treated with polyurethane was tested according to JIS L-0846A method, except that silk cloth was attached instead of nylon cloth, and the stain degree of the silk cloth was judged in gray scale. .

The dye used in this example was prepared as follows.

Disperse 5.4 g of the dye shown in 20 ml of dimethylformamide, add 1.8 g of CuCN at 20 ° C., stir at 50 ° C. for 2 hours for cyanation, then dilute with 20 ml of methanol and filter the precipitated crystals, It was washed with water and dried to obtain the monoazo dye (green crystal) of the present invention (yield 90%). The λmax of this product
(Acetone) was 522 nm.

Example 2 The following structural formula Was mixed with 0.5 g of a naphthalenesulfonic acid-formaldehyde condensate and finely pulverized with a paint shaker to obtain a finely divided dye. It was thoroughly mixed with a base paste having the following composition to obtain 100 g of color paste.

Composition of original paste Carboxymethyl cellulose paste 30 g Tartaric acid 0.2 g Aromatic carrier 0.3 g (San Floren SN, manufactured by Nichika Chemical Co., Ltd., trade name) Water 68.5 g Total 99.0 g This color paste on polyester fiber After printing, intermediate drying at 100 ° C, then holding in 170 ° C superheated steam for 7 minutes to develop color, and then soaping, washing with water and drying, light fastness, sublimation fastness and A blue printed polyester fabric with good wet fastness was obtained.

The wet fastness of the obtained dyed fabric after polyurethane processing was measured in the same manner as in Example 1 and the results are shown in Table 1.

The dye used in this example was made according to the method described in Example 1. The λmax (acetone) of this product was 600 nm.

Comparative Examples 1 and 2 A polyester cloth was dyed with the dyes shown in Table 1, and the obtained dyed cloth was measured for wet fastness in the same manner as in Example 1 after the polyurethane processing. Shown in the table.

Example 3 A polyester cloth was dyed according to the method of Example 1 using the dyes shown in Table 2 to obtain a dyed cloth having the color tone shown in the table.

The resulting dyed fabric was measured for wet fastness (alkali sweat fastness) after processing with polyurethane, and the results shown in Table 2 were obtained.

In Table 2, Ph means a phenyl group.

(Effects) As shown in the above examples, the monoazo dye of the present invention is not only said to have high fastness after dyeing, but the dyed cloth may be treated with polyurethane for the purpose of improving texture, waterproofing or antistatic, or the like. It has extremely high wet fastness (fastness after post-processing) after silicon processing or the like.

Therefore, the monoazo dye of the present invention is particularly suitable as a dye for high-quality clothing to be post-processed.

Claims (2)

[Claims] 1. The following general formula [I] [In the formula, X is a hydrogen atom, chlorine atom, bromine atom, nitro group, cyano group, C _1-4 alkyl group, C _1-4 alkoxy group, CF
₃ groups, SO ₂ R ″ groups or COR groups, wherein R and R ′ are each independently a hydrogen atom; C _1-8 alkyl group; C _1-8 alkoxy group, cyano group, chlorine atom, acyloxy group, C _{1 -8} alkoxycarbonyl group, C _1-8 alkoxycarbonyloxy group, benzyloxycarbonyl group, phenoxyethyloxycarbonyl group, benzyloxycarbonyloxy group, allyloxy group or C _1-4 alkyl group which may be substituted with aryl group An allyl group; or a phenyl group, R ″ represents a C _1-8 alkyl group or a phenyl group, R represents a hydrogen atom or a C _1-8 alkyl group, and Y represents a hydrogen atom, a chlorine atom or C _{1- 4} represents an alkoxy group]. 2. The following general formula [I] (In the formula, X is hydrogen atom, chlorine atom, bromine atom, nitro group, cyano group, C _1-4 alkyl group, C _1-4 alkoxy group, CF
₃ groups, SO ₂ R ″ groups or COR groups, wherein R and R ′ are each independently a hydrogen atom; C _1-8 alkyl group; C _1-8 alkoxy group, cyano group, chlorine atom, acyloxy group, C _{1 -8} alkoxycarbonyl group, C _1-8 alkoxycarbonyloxy group, benzyloxycarbonyl group, phenoxyethyloxycarbonyl group, benzyloxycarbonyloxy group, allyloxy group or C _1-4 alkyl group which may be substituted with aryl group An allyl group; or a phenyl group, R ″ represents a C _1-8 alkyl group or a phenyl group, R represents a hydrogen atom or a C _1-8 alkyl group, and Y represents a hydrogen atom, a chlorine atom or C _{1- 4} represents an alkoxy group).