JPS58201855A - Mixed dye for polyester fiber - Google Patents

Abstract

PURPOSE:To obtain a mixed dye, capable of dyeing polyester fibers in bright navy blue color having improved various fastnesses, and having improved temperature and pH stability, by mixing a disazo dye with a novel disazo dye or monoazo dye. CONSTITUTION:A mixed dye obtained by mixing a disazo dye of formula I with at least one selected from a novel disazo dye of formula II (X is Cl, NO2 or CF3; Y is CN, alkoxycarbonyl or carbamoyl; Z is H, Cl, CH3 or acylamino; R<1> and R<2> are H, cyclohexyl, aryl, alkenyl, aralkyl, alkyl, or substituted lower alkyl) and a monoazo dye of formula III(X<1> is Cl or Br; Y<1> is H, OCH3, OC2H5 or OC2H4OCH3; R<5> is CH3 or C2H5; R<3> and R<4> are substituted alkyl). The novel dye of formula II is prepared by diazotizing an aniline of formula IV, couping the diazotized aniline with a compound of formula V, diazotizing the coupling product, and coupling the diazotized product.

Description

[Detailed Description of the Invention] The present invention is a polyester fiber that is dyed in a vivid navy blue color with excellent fastness to light, sublimation fastness, water fastness, etc., and has excellent temperature stability during dyeing. and P.H.
This invention relates to a blended dye for polyester fibers with good stability.

The blended dye for polyester fibers of the present invention is a disazo dye represented by the following structural formula (1), and the following general formula [l[) (wherein, X represents a chlorine atom, a nitro group, or a trifluoromethyl group, Y represents a cyano group, an alkoxycarbonyl group, or a carbamoyl group, 2 represents a hydrogen atom, a chlorine atom, a methyl group, a hydroxyl group, or an acylamino group, and R1 and R2 represent a hydrogen atom, a cyclohexyl group, an aryl group, or an alknyl group. , aralkyl group, alkyl group or hydroxyl group, lower alkoxy 3-oxy group, aryloyloxy group, aryloxy group, lower alkoxycarbonyl group, lower alkoxyalkoxycarbonyl group, aralkyloxycarbonyl group, lower alkoxycarbonyloxy group, cyano group , represents a lower alkyl group polysubstituted with a halogen atom, an alkenyloxy group or a tetrahydrofuryl group. , represents an ethoxy group or a methoxyethoxy group, R6 represents a methyl group or an ethyl group, R1 and a spear represent a hydrogen atom, an aryl group, an alkenyl group, a cyclohexyl group, an aralkyl group, an alkyl group, or a human 4-monocytyl group, a lower alkoxy group. , lower alkoxyalkoxy group, lower alkanoyloxy group, chlorolower alkanoyloxy group, aryloyloxy group, aryloxy group, lower alkoxycarbonyl group, lower alkoxyalkoxycarbonyl group, aralkyloxycarbonyl group, lower alkoxycarbonyloxy group , halogen atom,
It represents a lower alkyl group polysubstituted with an alkenyloxy group or a tetrahydrofuryl group. ) This is a blended dye for polyester fibers containing at least one selected from the monoazo dyes shown below.

To explain the present invention in detail, the compound represented by the general formula (n) is a new disazo dye, and the acylamino group represented by 2 in the general formula [lI] is an acetylamino group, a propionylamino group, a chloro Acetylamino group, benzoylamino group, methylsulfonylamino group,
Examples include a chloropropionylamino group, an ethoxycarbonylamino group, and an ethylaminocarbonylamino group.

Also, in general formula [■] and general formula (1), R'
, R'', R8 and R4 include phenyl group, )!J2 group, chlorophenyl group, etc., alkenyl group includes allyl group, crotyl group, etc., and aralkyl group includes benzyl group, etc. , phenethyl group, chlorobenzyl group, etc. R1
, R, The alkyl group represented by R3 and R4 includes a methyl group, an ethyl group, a linear or branched propyl group, a methyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, etc. It will be done. R1゜R”,
The substituted lower alkyl group represented by R''M and R4 includes a hydroxyl group; a lower alkoxy group such as a methoxy group, an ethoxy group, and a butoxy group; a methoxyethoxy group,
Lower alkoxyalkoxy groups such as ethoxyethoxy groups;
Lower alkanoyloxy groups such as acetyloxy and propionyloxy groups; chlorolower alkanoyloxy groups such as chloroacetyloxy and chloropropionyloxy groups; aryloyloxy groups such as benzoyloxy; aryloxy groups such as phenoxy; methoxy Lower alkoxycarbonyl groups such as carbonyl group and ethoxycarbonyl group; Lower alkoxyalkoxycarbonyl groups such as methoxyethoxycarbonyl group and ethoxyethoxycarbonyl group; Aralkyloxycarbonyl groups such as benzyloxycarbonyl group; Methoxycarbonyloxy group, ethoxy Examples include lower alkoxycarbonyloxy groups such as carbonyloxy groups; halogen atoms such as chlorine atoms and bromine atoms; lower alkyl groups substituted with alkenyloxy groups such as allyloxy groups and crotyloxy groups, or tetrahydrofuryl groups.

The structural formula shown above [! ] The disazo dye represented by (hereinafter referred to as disazo dye [summer])
and Patent Application Shoj≦-go/7!2, etc.

The disazo dye represented by the general formula [II] (hereinafter referred to as disazo dye (II)) is, for example, the disazo dye represented by the following formula [
IV) (In the formula, the same as the above definition of Company X) Diazotizes the aniline represented by
A monoazo dye represented by the following formula (Vl) (wherein X and Y are the same as defined above) obtained by coupling with a co-aminothiophene represented by diazotized,
It can be produced by coupling with diphenylmethane-based amines represented by the following general formula [■] 8- (wherein Z, R1 and R2 are the same as defined above).

The monoazo dye represented by the general formula (1) (hereinafter referred to as monoazo dye CI) is disclosed in Japanese Patent Publication Publication No. 3, No. 3, No. 200 and No. 7,
Special public official? -, 2ggoj3, special public Akari θ-2! G3/,
Special public Sho 4tO-27J”4t, Special public Shogu/-6707t
<Isobaric is described.

The disazo dye [■], disazo dye Cl0), and monoazo dye CI) used as compounding components of the compounded dye of the present invention are each high-performance dyes capable of dyeing polyester fibers in a navy color with good fastness. However, when each component dye is used individually by dyeing polyester fibers by mixing disazo dye (1) with at least one selected from disazo dye [III # and monoazo dye (1)]. It is industrially advantageous because the dye bath exhaustion is dramatically improved and the build-up property is also very good, making it easy to obtain highly concentrated dyed products and reducing unnecessary loss of dye. It is.

The number of component dyes in the blend is preferably 3 or 3 types, and the blend ratio is preferably approximately the same as each component, but is not limited depending on the purpose.

A part of the blended dye of the present invention can also be obtained by blending respective intermediates during production (diazotization, coupling).

Fibers that can be dyed with the blended dyes of the present invention include polyester fibers such as polyethylene terephthalate, polycondensates of terephthalic acid and/or coubis-(hydroxymethyl)cyclohexane♂, and natural fibers such as cotton, silk, and wool. Examples include blended products and mixed fiber products of fibers and the above-mentioned polyester fibers.

Enjoy the blended dye of this invention! To dye polyester fibers, disazo dyes [1], disazo dyes [■], and monoazo dyes [2] are insoluble or sparingly soluble in water, so naphthalene sulfonic acid and formaldehyde are used as dispersants by a conventional method. Dyeing or printing may be carried out by preparing a dyeing bath or printing paste by dispersing it in an aqueous medium using a condensate of ester, a surface alcohol sulfate, a higher alkylbenzene sulfonate, etc. For example, in the case of dyeing,
By applying ordinary dyeing methods such as high-temperature dyeing, carrier dyeing, and thermosol dyeing, it is possible to dye polyester fibers or their blends with fast dyeing. At that time, in the case of VC, add phosphoric acid to the dyeing bath.
Even better results can be obtained by adding acidic substances such as acetic acid, phosphoric acid or ammonium sulfate.

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 unless the gist of the invention is exceeded.

Examples/~/Otsu-disazo dyes [■] Disa-11-zo dyes described in Table 1-/[U-/)-[■-/Machi and monoazo dyes described in Table-2 [w-/)-[ 1-//) alone or in combination as shown in Table 3 to give a total of /I of naphthalene sulfonic acid-formaldehyde condensate/g and higher alcohol sulfuric ester, 2. ! Polyester m male/θθg was immersed in a dyeing bath dispersed in water 31 containing 73
After dyeing at 0° C. for θ minutes, washing with water and drying, a navy 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.

In addition, the dye dyed on the dyed fabric was dissolved and extracted using a dimethylformamide solution of 0.027% phosphoric acid, and the dye dyed on the dyed fabric was determined colorimetrically. The concentration was calculated and shown in Clothing-3.
ll-/”J/, θg ?θC1) θ, tl /-3 combination /da0 [-7)θ, 69 2,:a-/(rr-accepted]/, θg ♂Oλ-ko [
rr-3) Cθy (1'θ[l) θ
, O1. 2-i [-2] θ,, 2J-17 combination /g θ [11-3] 0.2tg J 3-/ [1-/) /, θg and 0,, ,'
) ,,, :)* -yz.

(+)0. 3rd-+2 Doug-/[■-gu]/, θl/ J'θgu λ[I
-ko) /, 01/ /θ[I''
(]・Yu J Gu -3 [1 Thorn) 0.3g
Self-match/ri.

[x-a]o, :tg ! ! -/[■-ta]/+θg? θ

Claims (1)

[Scope of Claims] ([) A disazo dye represented by the structural formula: 2 represents a hydrogen atom, a chlorine atom, a methyl group, a hydroxyl group, or an acylamino group, and R1 and R2 represent a hydrogen atom, a cyclohexyl group, an aryl group, an alkenyl group, an aralkyl group, an alkyl group, a hydroxyl group, or a lower alkoxy Alkanoyloxy group, aryloyloxy group, aryloxy group, lower alkoxycarbonyl group, lower alkoxycarbonyl group, aralkyloxycarbonyl group, lower alkoxycarbonyloxy group, cyano group, ) 10 atoms/atom, alkenyloxy group or tetrahydro Represents a lower alkyl group polysubstituted with furyl groups. ) and the general formula (wherein, XI represents a chlorine atom or a bromine atom, and yl
represents a hydrogen atom, a methoxy group, an ethoxy group, or a methoxyethoxy group, R1+ represents a methyl group or an ethyl group, and R3R and R' represent a hydrogen atom, an aryl group, an alkenyl group, a cyclohexyl group, an aralkyl group, an alkyl group, or a hydroxyl group. group, lower alkoxy group, lower alkoxyalkoxy group, lower alkanoyloxy group, chlorolower alkanoyloxy group, aryloyloxy group,
Excludes a lower alkyl group polysubstituted with an aryloxy group, a lower alkoxycarbonyl group, a lower alkoxyalkoxycarbonyl group, an aralkyloxycarbonyl group, a lower alkoxycarbonyloxy group, a haloken atom, an alkenyloxy group, or a tetrahydrofuryl group. ) A blended dye for polyester fibers containing at least one selected from the monoazo dyes shown in the following.