JPS5838754A - Azo dye for polyester fiber - Google Patents

Abstract

NEW MATERIAL:A compound shown by the formulaI[D is (substituted) phenyl, (benzo)thiazolyl, thienyl, pyridyl, etc.; X is H, Cl, Br, methyl, or acylamino; Y is H, Cl, methyl, or alkoxy(alkyl); R<1> and R<2> are H, (substituted)alkyl, cycloalkyl,alkenyl or aryl]. EXAMPLE:A compound shown by the formula II. USE:A dye dyeing polyester fibers in yellow - blue green, having improved fastness to light, fastness to sublimation, fastness to water, and temperature and pH stability during dyeing. PROCESS:An amine shown by the formula D-NH2 is diazotized and coupled with a compound shown by the formula III.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an azo dye for polyester fibers, and more specifically, it dyes polyester fibers from yellow to bluish green, and dyes polyester fibers in various degrees of hardness: 4! This relates to an azo dye that has excellent light resistance, sublimation resistance, and water resistance, as well as excellent temperature stability and pH stability during dyeing.

The azo dye for polyester fibers of the present invention has the following general formula (
1) (In the formula, D represents a substituted or unsubstituted phenyl group, thiazolyl group, benzothiazoyl group, thiadiazolyl group, chenyl group, or pyridyl group, and X represents a hydrogen atom, chlorine atom, bromine atom, methyl group, or azila τ represents a water atom, a chlorine atom, a methyl group, an alkyl group, a circle represents an alkyl group, R and IL
婹 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a cyclohexyl group, and an alkenyl group 9 represents an ary group.

) is an azo dye for polyester fibers.

The substituted or unsubstituted 7-ethyl group, thiazolyl group, benzothiazolyl group, thiadiazolyl group, and bicidyl group represented by D in the above general formula (I) include phenyl group; fluorine atom, chlorine atom, Bromine atom, methyl group, ethyl group, methyl group, methoxy group, methoxy group, phenylazo group, cyano group, nido group, methylsulfoyl group, ethylsulfonyl group, adalsulfoyl group, lower alkoxycarboxyl ha, low i
l-alkoxyethoxycarpnyl group, aryloxyethylcarpnyl group, lower alkyl group, di-lower alkyl group, diallylaminocarpyl group, noaryl group group, dimethylaminosulfonyl group, diethyladenosulfonyl group,
A phenyl group substituted with a monomethyladenosulfoel group, a monoethyladenosulfoel group, an acetyl group, a phenyl group, etc.; a thiazosyl group; a benzothiazolyl group; a methyl group, a chlorine atom, a bromine atom, a nido tetragroup, a lower alkoxyl group Nyl group, methoxycarbuel group, ethoxy'z) now dicarbonyl group, trifluoromethyl group, methylsulfonyl group, etc.) substituted with the thiazolyl group; 9 is benzothiazolyl group; thiadiazolyl group; lower alkyl group; phenyl group, benzylene group, 7enethyl group, citer
alkyl group, lower alkylthio group, lower alkylsulfinyl ft, lower alkylsulfonyl group, cyano group, chlorine atom, arylthio group, arylsulfinyl group, arylsulfonyl group, etc.) substituted ninethiadiazolyl group; chenyl Group; chlorine atom, bromine atom, methyl group,
A chenyl group substituted with a trifluoromethyl group, a phenylazo group, a cyanogen group, a lower alkylsulfonyl group, an acetyl group, a holyl group, a lower alkoxyorbonyl group, an aminocarnyl group, etc.; Examples include pyridyl groups which can be substituted with chlorine atom, bromine atom, nido group, methyl group, methyl sulfate group, cyano group, etc.; examples of the azilazno group represented by I include acetylaceno group, cyano group, etc.; Acetyl acetyl group, benzyl azo group, methylsulfony l group, tarotobouvio crystal lua ζ
Examples include ethyl-a-electronic group, ethyl-a-electronocarboerua-deno group, etc. Examples of the alkoxy group represented by 1 include methoxy group, methoxy group, etc., and examples of the al;
Examples of the unsubstituted alkyl group represented by and W include a methyl group, an ethyl group, a linear or branched O-propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, etc. , Substituted alkyl groups include methoxyethyl group, ethoxyethyl group, butoxyethyl group, etc.
Lower alkyl; lower alkyl group which may be substituted with O; human tm diethyl group, human-
Substituted hydrodialkyl groups such as xibuvir group, dibutyl group, k-doxycyl group, --human l1dPcyJ-methoxybuvir group; cyanomethyl group, cyanoethyl group, etc. Cyano lower alkyl group; optionally substituted acyl lower alkyl group such as acyl diethyl group, teryl diethyl group, probiotic ethyl group, penzoyl ethyl group; methoxycarboxyl group methoxyethyl group, methyl, shed, gx, ruoxyethyl group, etc., alkyl group, ethyloxy lower alkyl group; Wel methyl group, met life 8/★ report=xzchi)y
group, -C)* optionally substituted alkyl group of cycarpolyethyl group, methoxycarbonylmethyl group, dicarboxylic group, methoxyethoxycarbonylmethyl group, benzyloxycarbonylmethyl IaIIi; Reboel lower a# radical: benzyl group, 7
Optionally substituted aralkyl groups such as enethyl 1, 11-benzyl groups;
Carbonyl lower alkyl group: tetrafluoride 71 group; succinic acid 2 doethyl group 410 succinic acid indo-lower alkyl group; Examples of the alkenyl group include an ethyl group and a V anomethoxyl group; examples of the alkenyl group include an allyl group and a cutyl group; examples of the aryl group include a 7-el group, a 7-ethyl group, and a) WIN! F# is mentioned.

The noazo dye represented by the above general formula (I) has the following formula [Otori] I)-11!1. 1111611111111
66 To diazotize an acene compound represented by [Otori] (in the formula, p is the same as 94 in the above definition) and form it by a chemical compound represented by the following formula [Otori] and a coupler broken by a). I can do it.

Fibers that can be dyed with this FIAo azo dye include:
Polyethylene terephthalate, tere-7meric acid and/or II
-Bis-(dimethyl) sifter, nano and O polyester fibers such as polycondensed metals, or natural fibers such as cotton, silk, sheep I@, and the above polyester fibers.
181 crystal and Amori crystal are mentioned.

In order to dye polyester fibers using a 181i dye from scratch, the dye represented by the general formula (1) shown above is added to water.
*In an aqueous medium using a dispersing agent of 0, which is 0 and a conventional method), a condensate of naphthalene sulfonic acid and formaldehyde with O, a higher alcohol sulfuric ester, and a higher alcohol lupene (sulfonate, etc.). You can prepare a printing dye by dispersing it in the dyeing bath, and then perform dyeing or printing.
For example, in the case of dyeing, ordinary dyeing methods such as high temperature dyeing, carrier dyeing, and ner-sol dyeing are applied.
Polyester fibers or polyester fibers are made with excellent dyeing properties. In that case, depending on the case),
Formic acid and acetic acid in the dye bath! Even better results can be obtained by adding an acidic substance such as carbonic acid or ammonium sulfate.

411 to the method of the present invention! General formula (1) used
The dyes indicated by are the same type! It may be used in combination with IO dyes or dyes of other systems, and good results may be obtained with ζO dyes, such as O china clay, which is expressed by the general formula (1) shown above and is dyeable by mixing O with dyes.

Next, the present invention will be explained in more detail using examples: h
However, this invention is the l! Not exceeding @) or less 0*11
It is not 10 limited to 111tf4.

l! Koji Example 1 Structural formula shown below II Mark dye 0.11
Disperse water JlK containing formaldehyde reduced metal 11 and higher alcohol sulfuric ester Jl to prepare 1 liter of dyeing bath.
It was j1. Polyester fiber 10121 was immersed in this dyeing bath and dyed at 730°C. After staining for a minute, soaping,
After washing and drying, a bright reddish-blue dyed fabric can be obtained. The dyed fabric obtained had good resistance to color, sublimation rate, and water resistance, and the temperature stability and pH stability of the above-mentioned dye at the time of kiln color were good.

The dye used in this example was manufactured as follows.

No door light! - Nidroti2zole t and Tsu I were dissolved in 10 @ sulfuric acid t011Jlll, and diazotized using nidotetrasyl sulfuric acid at j~-J'C to obtain a good diazo! rim salt sttg
-Ethyl-Summer-Ethoxylic I Nilp-Nibil Aniline 1
1. Dissolve 1 tptidK of methanol and add kJ"cK: to the 9II solution, stir for 1 hour at the same temperature to precipitate the 9 monoazo dye. After several P, wash with water and dry.
Is wax (acetone) 1? /n Otori with 6 and 9.

Example 1 Using the dye represented by the structural formula below, a positive ester fiber M was dyed in the same manner as in Example 1, and a bright bluish red O dyed fabric was obtained. 9.Dyeed fabric O light resistance, sublimation resistance and water resistance, and o*yt stability during dyeing of the above aS, 1
M stability is good.

The dyes that can be used in this example are ll! Vagina Example/Produced in accordance with the product, λmhx (acetone) jJffnm.

Example J Dye represented by the following structural formula 0.1jlt-7talenesulfonic acid-
Dye dispersion wave obtained by mixing with formaldehyde condensate Jl and water ginseng I and grinding with a sand grinder for an hour and carrier (May Printer Y-, Jj (trademark), Meisei Kagaku Mal) mixed into Jjt textile printing @q01 Prepare the color paste.9.

This color paste was printed on a polyester textile material, dried at 100℃ for 1 minute, then heated at 10℃ to fix the dye, and after soaping, washing with water, and drying, it became light-resistant. A vivid bluish-red dyed fabric with excellent strength and sublimation resistance can be obtained. The λwax (acetone) of this product is IJtn Otori.

Example - When polyester fibers were dyed in the same manner as in Example 1 using the dye represented by the structural formula below, a dyed fabric with a clear borderline color was obtained. The light resistance, sublimation resistance and water resistance of the obtained dyed fabric, and the temperature stability during dyeing of the above dye, P1!
Stability is good and round.

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

The λ Peng X (acetone) of this product is 44 JN Peng.

Example I Polyester fibers were dyed using the dyes shown in the table below (in the same manner as in Example 1) to obtain dyed products having the tones shown in the table.

Claims (1)

[Scope of Claims] 5 (in the formula, D represents a substituted or unsubstituted phenyl group, thiazolyl group, pydithiazolyl group, thiadiazolyl group, chenyl group, or pyridyl group, and X represents a hydrogen atom, a chlorine atom, Represents a bromine atom, methyl group or azyla group, and! represents a hydrogen atom, a chlorine atom, a methyl group, a 7kW KV group, where the front is an alkyl group, llI and D represent a water bulk atom, and the substitution is an unsubstituted Oa, an alkyl group, a cyclohexyl group, an alkezest Nine represents an aryl group. ) is an azo dye for positive ester fibers.