JPS59145254A - Disazo dye for polyester fiber - Google Patents

Abstract

PURPOSE:To provide a disazo dye for polyester fibers, whichdyes polyester fibers green with excellent fastness to light in particular and is water-insoluble, having a specified structural formula. CONSTITUTION:The titled disazo dye for polyester fibers is obtd. from a compd. of formula I (wherein R' is H, F, Cl, Br, nitro, cyano,lower alkyl sulfonyl, lower alkoxycarbonyl, formyl, thiocyanato, trifluoromethyl; X is H, methyl, ethyl, phenyl; Y is cyano, lower alkoxy carbonyl, carbamoyl which may be substituted with lower alkyl; R<2> is H, Cl, Br, methyl, methoxy, hydroxymethyl, alpha- hydroxyethyl, formyl, a group of formula II or III, acylamino; R<3>, R<4> are each alkyl, substd. alkyl, cyclohexyl, aryl, alkenyl).

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a disazo dye for polyester fibers.
This invention relates to disazo dyes that are excellent in various fastnesses, especially light fastness.

The disazo dye for polyester fibers of the present invention has the following general formula (1) (wherein R1 is a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a nitro group, a cyano group, a lower alkylsulfonyl group, a lower alkoxycarbonyl group, represents a formyl group, a thiocyanate group or a trifluoromethyl group, X represents a hydrogen atom, a methyl group, an ethyl group or a phenyl group, and Y represents a carbamoyl group optionally substituted with a cyano group, a lower alkoxycarbonyl group or a lower alkyl group R2 represents a hydrogen atom, a chlorine atom, a bromine atom, a methyl group, a methoxy group, a hydroxymethyl group, an α-hydroxyethyl group, a formylcylamino group, and Ha and R4 represent an alkyl group, a substituted alkyl group, a cyclohexyl group , represents an aryl group or an alkenyl group).

In the general formula CI), examples of the lower alkoxycarbonyl group represented by R1 and Y include methoxycarbonyl group, ethoxycarbonyl group, butoxycarbonyl group, and may be substituted with a lower alkyl group represented by Y. As a carbamoyl group, a carbamoyl group,
N-methylcarbamoyl group, N-ethylcarbamoyl group, N-butylcarbamoyl group, N,N-dimethylcarbamoyl group, N,N-diethylcarbamoyl group, etc., and the lower alkylsulfonyl group represented by R1 is , methylsulfonyl group, ethylsulfonyl group, etc., and examples of the acylamino group represented by R2 include acetylamino group, chloroacetylamino group, benzoylamino group, methylsulfonylamino group, chloropropionylamino group, ethoxycarbonylamino group, ether Examples of the alkyl group represented by R11 and R4 include an aminocarbonylamine group, a methyl group, an ethyl group, a linear or branched prophylactic group, a butyl group, a pentyl group, a hexyl group, a heptyl group, Substituted alkyl groups include lower alkoxyalkyl groups such as methoxyethyl, ethoxyethyl and butoxyethyl groups; lower alkoxyalkoxyalkyl groups such as methoxyethoxyethyl and ethoxyethoxyethyl; phenoxyether groups; Phenoxyalkyl groups such as benzyloxyethyl group, chlorobenzyloxyether group, etc.; optionally substituted aralkyloxy lower alkyl groups such as hydroxyethyl group, hydroxypropyl group, hydroxybutyl group, hydroxyhexyl group, euhydroxy-3 -Optionally substituted hydroxyalkyl groups such as methoxypropyl group; cyanogen lower alkyl groups such as cyanomethyl group and cyanoethyl group; acetyloxyethyl group, chloroacetyloxyethyl group, chloropropionyloxyethyl group, benzoyloxyethyl group, etc. An optionally substituted acyloxy lower alkyl group; an alkoxycarbonyloxy lower alkyl group such as a methoxycarbonyloxyethyl group or a methoxyethoxycarbonyloxyethyl group; a carbamoyl lower alkyl group such as a carbamoylmethyl group or a carbamoylethyl group; a methoxycarbonylmethyl group , an optionally substituted alkoxycarbonyl lower alkyl group such as an ethoxycarbonylmethyl group, a methoxyethoxycarbonylmethyl group, a benzyloxycarbonylmethyl group; an optionally substituted aralkyl group such as a benzyl group, a phenethyl group, a chlorobenzyl group, etc. ,
Allyloxycarbonyl □Allyloxycarbonyl lower alkyl groups such as ethyl group and allyloxycarbonylmethyl group; Tetrahydrofurfuryl group: Succinimide lower alkyl group such as succinimide ether group; Heptatalymide lower alkyl group such as phthalimidoethyl group Groups; Examples include cyanoalkoxy lower alkyl groups such as cyanoethoxyethyl group and cyanomethoxyethyl group, halogeno lower alkyl groups such as chloroether group, and aryl groups include phenyl group, chlorophenyl group, methylphenyl group, etc. Examples of the group include an allyl group and a tetratyl group.

The disazo dye represented by the general formula CI) is represented by the following formula [1
1] Diazotize amines represented by R1 (wherein R1 is the same as defined above) to form aminothiophenes represented by the following formula [l) (wherein X and Y are the same as defined above) and a cup. The resulting monoazo compound represented by the following formula (IV) 1 (wherein, R1, and R4 are the same as defined above).

Fibers that can be dyed with the disazo dye of the present invention include:
Polyethylene terephthalate, terephthalic acid and/or lI
- Other polyester fibers such as polycondensates with bis-(hydroxymethyl)cyclohexane, or natural fibers such as cotton, silk, and wool; Blended products of acetate fibers such as diacetate fibers and triacetate fibers with the above polyester fibers, Examples include mixed fiber products.

In order to dye polyester fibers using the dye of the present invention, since the dye represented by the general formula [I] is insoluble or sparingly soluble in water, naphthalene sulfonic acid and formaldehyde are used as dispersants in a conventional method. A dyeing bath or printing paste prepared by dispersing in an aqueous medium using a condensate of ester, higher alcohol sulfuric ester, higher alkylbenzene sulfonate, etc. may be prepared, and immersion dyeing or printing may be performed. For example, in the case of dip dyeing, polyester fibers or their blends can be dyed with excellent fastness by applying ordinary dyeing methods such as high temperature dyeing, carrier dyeing, and thermosol dyeing. In this case, even better results can be obtained if, if necessary, acidic substances such as formic acid, acetic acid, phosphoric acid or ammonium sulfate are added to the dyeing bath.

Furthermore, the dye represented by the forepaw general formula [I] used in the method of the present invention may be used in combination with dyes of the same type or dyes of other systems. Depending on the combination, good results such as improved dyeability may be obtained.

Next, the present invention will be explained in more detail with reference to examples, but the present invention is not limited to the following examples as long as the gist thereof is not exceeded.

Example 1 A polyester fiber 1009 was immersed in a dye bath in which the dye OOS represented by the following structural formula was dispersed in 3 tons of water containing a naphthalene sulfonic acid-formaldehyde condensate /f and a higher alcohol sulfate 2f, and dyed at /30C. After dyeing for 60 minutes, soaping, washing and drying,
A blue dyed fabric was obtained. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric, as well as the temperature stability and pH stability during dyeing of the above dye, were good.

The dye used in this example was produced as follows.

Anilinde, 32 in 7% hydrochloric acid/! The solution was cooled to 2C and then -N-sodium nitrite! Added rOml. At this time, the temperature was set not to exceed IC. The obtained aniline diazonium salt solution was mixed with 1-amino-3-cyanothiophene/2. Add Da 2 to a solution of 200 ml of methanol at CoC, stir at the same temperature for 2 hours, and precipitate the monoazo compound ###
##After filtering the material, it was washed with water and dried. This monoazo compound I (2-amino-3-cyano-phenylazothiophene) //, lI? Acetic acid/! rO, rrtl and phosphoric acid/! nitrosyl sulfuric acid (sodium nitrite 3.S
? (prepared by dissolving 97 sulfuric acid, 2o7) was gradually added thereto, and the mixture was stirred for 3θ minutes at the same temperature to prepare a diazo solution of a monoazo compound.

N,N-diacetoxy ether-1)-)luidine/4
．． Dissolve 7F in 200ml of methanol and add 200ml of ice.
? and 10 od of water. The diazo solution prepared above was added to this and stirred for 2 hours at o-tc. The precipitated disazo dye was taken out of the oven, washed with water and dried. λm of this product
ax (acetone) was 65 nm.

Example: A dye represented by the following structural formula: 0. ! f is naphthalene sulfonic acid formaldehyde condensate/l and higher alcohol/I/sulfuric ester co? A dyeing bath was prepared by dispersing it in 3 tons of water containing the following. Polyester fiber 1001 was immersed in this dyeing bath, dyed at /30c for 6θ minutes, and then soaped, washed with water, and dried to obtain a blue dyed fabric. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric, as well as the temperature stability and pH stability during dyeing of the above dye were good.

The dye used in this example was produced according to Example 1 and separated by silica gel column chromatography (developing solution: chloroform). Is the λmax (acetone) of this product A2?
It was nm.

Example 3 Dye represented by the following structural formula θ, 5? was dispersed in 3 t of water containing 12 naphthalene sulfonic acid formaldehyde condensates and 22 higher alcohol sulfate esters to prepare a dyeing bath. 100f of polyester fibers were immersed in this dyeing bath, and /3θ
After dyeing with C for 6θ minutes, soaping, washing with water and drying were performed to obtain a blue dyed fabric. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric, as well as the temperature stability and pH stability during dyeing of the above dye, were good.

The dye used in this example was produced according to Example 1.

The λmax (acetone) of this product was 1.2 gnm.

Example D Dye represented by the following structural formula O,! rt, naphthalenesulfonic acid-
A dyeing bath was prepared by dispersing it in 3 tons of water containing formaldehyde condensate/l and higher alcohol sulfuric ester it. Polyester fiber lθ01 is immersed in this dyeing bath,
After dyeing at /30C for AO minutes, soaping, washing with water and drying were performed to obtain a blue dyed fabric. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric, as well as the temperature stability and pH stability during dyeing of the above dye, were good.

The dye used in this example was produced according to Example/.

The λmax (acetone) of this product was b3gnm.

Example S Dye O, St represented by the following structural formula was converted into naphthalenesulfonic acid-
Formaldehyde condensate/? A dyeing bath was prepared by dispersing it in 3 tons of water containing 1 and higher alcohol sulfate ester. Immerse 100f of polyester fibers in this dyeing bath,
After dyeing at /3θC for 6θ minutes, soaping, washing with water and drying were performed, and a blue dyed fabric was obtained. The light fastness, sublimation fastness and water fastness of the obtained dyed fabric, as well as the temperature stability and pH stability during dyeing of the above dye, were good.

The dye used in this example was produced according to Example/.

The λmax (acetone) of this product was 6.7 A nm.

Example 6 Polyester fiber dyeing was carried out in the same manner as in Example 1 using the dyes shown in the table below to obtain dyed products having the colors shown in the table.

Table -l general formula

Claims (1)

[Claims] (1) General formula (wherein R1 is a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a nitro group, a cyano group, a lower alkylsulfonyl group, a lower alkoxycarbonyl group, a formyl group, a thiocyanate group, or a trifluoromethyl group) represents a hydrogen atom, a methyl group, an ethyl group, or a phenyl group, Y represents a cyano group, a lower alkoxycarbonyl group, or a carbamoyl group optionally substituted with a lower alkyl group, R2 represents a hydrogen atom, a chlorine atom, Bromine atom, methyl group, methoxy group, hydroxymethyl group, α-hydroxyethyl group, formyl M, “H*0”z”; t:
R3 and R4 represent an alkyl group, a substituted alkyl group, a cyclohexyl group, an aryl group or an alkenyl group. ) Disazo dye for polyester fibers.