US3043647A

US3043647A - Colouring of polyester fiberes

Info

Publication number: US3043647A
Application number: US706896A
Authority: US
Inventors: Kopp Georges; Gangneux Rene Eugene Marcel; Baron Alfred Maxime Edouard
Original assignee: CIE FRANCAISE DES MATIERS COLO
Current assignee: CIE FRANCAISE DES MATIERS COLO; FRANCAISE DES MATIERS COLORANTES Cie
Priority date: 1957-01-05
Filing date: 1958-01-03
Publication date: 1962-07-10
Anticipated expiration: 1979-07-10

Description

United States PatentOfice 3,043,647 COLOURING F POLYESTER FIBRES Georges Kopp, Mont-Saint-Aignan, Ren Eugene Marcel Gangneux, Rouen, and Alfred Maxime Edouard Baron, Paris, France, assignors to Compagnie Francaise des Matieres Colorantes, Paris, France, a French company No Drawing. Filed Jan. 3, 1958, Ser. No. 706,896

Claims priority, application France Jan. 5, 1957 4 Claims. (Cl. 8-41) The present invention concerns improvements in the colouring of polyester fibres.

It is known that it is possible to dye polyester fibres by means of the so-called plastosoluble dyestuffs, which are used for dyeing cellulose acetate fibres. These dyes can be applied either at ordinary pressure in the presence of carriers, the most common of which are o-phenylphenol and the chlorinated derivatives of benzene, or under superatmospheric pressure and consequently in the absence of carriers and in a shorter time. The shades obtained are generally rather bright; in many cases, however, they 'lack fastness, especially to light, to wet tests and to sublimation.

It is further known that it is possible to dye polyester fibres, under the conditions used for the so-called plastosoluble dyestuffs, by means of mixtures of diazotisable bases and coupling compounds belonging to the series of arylides of ,B-hydroxynaphthoic acid. The corresponding pigments are formed on the fibre by simultaneous diazotisation and coupling. Provided that the choice of base and arylide and the relation between the amounts of these substances fixed on the fibre are correct, the colours obtained are capable of satisfying to a high degree the requirements so far as fastness to light and Wet tests are concerned. Although from the absolute point of View the resistance to sublimation is satisfactory, in numerous cases, however, variations in shades which can be considerable are observed at the time of preforming. In addition, this method of dyeing has the disadvantage of being lengthy since two successive treatments of the fibre are necessary.

It has already been proposed to dye, by conventional processes, certain textile fibres by means of very finely dispersed pigmental dyestuffs like those which are quite commonlyused for the coloration of viscose or cellulose acetate in bulk. In most cases, however, the tinctori-al yield is low and, in addition, the shades obtained are not sufficiently fast to rubbing for this solution to be capable of being applied in practice.

We have now found that dyestuifs of the general formula:

in which R represents the residue of a benzene amine and pheric pressure.

3,043,647 Patented July 10, 1962 X represents an alkyl group possess, at high temperature, an excellent aflinity for polyester fibres.

By the expression polyester fibres we mean quite generally the fibres obtained by the poly-condensation of di-acids with di-alcohols, and in particular those obtained by the poly-condensation of terephthalic acid with ethylene glycol. Such fibres are on the market under the names Terylene, Dacron and Tergal.

The dyestufis of the. above general Formula I can be applied to these fibres at a high temperature by any of the processes already used for the coloration of the latter by means of other pigments. Dyeing can be carried out, for example, under superatmospheric pressure andat temperatures above 0., preferably at temperatures be-' tween 101 C. and C., by means of aqueous dispersions of the dyestufis of general Formula 1. Another process comprises foularding the fibres by means of aque ous dispersions of these dyestuffs and then subjecting them to a treatment at high temperature, preferably between 150 C. and 200 C. Also, after foularding bymeans of these aqueous dispersions, the impregnated fibres can be subjected to steaming under super-atmos- Fabrics basedon polyester fibres can also be printed by means of pastes containing aqueous dispersions of the said dyestuffs and then the printed fibres subjected to'steaming under superatmospheric pressure.

Alkylarylsulphonat es and the products resulting from the condensation of sulphon-ated aromatic derivatives with aldehydes, such as the methylene-dinaphthylsulphonates, are particularly valuable auxiliary substances since they allow the preparation of a good dispersion of the dyestuflis and facilitate the taking up of the latter on the polyester fibres. On the other hand, carriers, such as monoor poly-chlorinated derivatives of the benzene series or diphenyl, can be added to the dye bath or to the printing pastes. These substances exert a swelling action on the polyester fibres and are capable of improving the tinctorial yield. 'Inaddition, it is useful, and particularly so in.

be remedied which in all probability is due to the accumulation of electrical charges as a result of the circulation of the bath around hydrophobic fibres.

The dyestuffs of general Formula I give, with excellent yields, bright shades characterised by very good fastness. These shades are not in general comparable with those obtained on cotton or obtained by coloration of viscose in bulk. *It is necessary to consider that the fact of operating at high temperature has the efiect of giving to the pigment its definitive physical form, a result which is certainly not attained when the pigment is formed on the polyester fibre by diazotisation and coupling.

The invention will be more clearly understood by reference to the following examples which are purely illustrative.

Example 1 3.5 parts of "monochlorotoluene are emulsified in 10 parts of water by means of about 1.5 parts of the butyl ester of sulphonated ricinoleic acid. This emulsion is stufiof the following formula:

QN N

(previously dispersed with 2 parts of the sodium salt of methylene-dinaphthylsulphonic acid) is mixed therewith. 100 parts of polyester fibres, previously degreased by treatmentin alkaline medium in the hot, areintroduced. The dyeing is carried out in an apparatus which enables it to be effected under slight superatrnospheric pressure, while the temperature is kept at 105 C. for an hour. The treatment is finished by subjecting the fibres to cleaning by ,alkaline reduction in a bath containing one to two grams .per litre of an alkylphenol-ethylene oxide condensate.

The polyester fibres are dyed a bright orange shade, which is fast to light, to wet tests, rubbing and sublimation.

' Example 2 3.5 parts of orthodichlorobenzene are emulsified in parts of water by means of about 1.5 parts of the butyl ester of sulphonate'd rici-noleic acid. This emulsion is poured into 1000 parts of tepid water and one part of the dyestuif of the formula: I

o c'in (previously dispersed by means 'of'2 partsoi the sodium salt of methylene-dinaphthylsulphon-ic acid). is mixed therewith. 100 parts ofa mixed material made up ofpolyester/wool 'fibres, previously degreased in the hot in a bath containing 21 to 2 g. per litre of an alkylphenol-ethylene oxide condensate, are introduced. Dyeing is effected under superatmospherio pressure while keeping the temperature at 105 C. for one hour.

The polyester fibres are dyed a bluish-red shade, fast .to light, wet tests, rubbing and sublimation, while the wool is only very slightly coloured. This light shade is not of such nature that it diminshes the quality of the acid dyestufi which must be applied simultaneously or subsequently to the wool; moreover, it readily disappears if the dyeing is followed by a slightly reducing cleaning treatment by means of a bath containing 1 to 2 g. per litre of an alkylphenol-ethylene oxide condensate.

Example 3 and On dyeing under the same conditions, a scarlet colour of good brilliancy is obtained which possesses excellent fastness, while the wool is sufficiently unaffected to allow it to be easily dyedzover.

(was

Example 4 A printing paste is prepared comprising the following constituents Parts 'dyest'uft'of'the formula:

dyestufi of the formula:

sodium methylene-dinaphthylsulphona te l O CzHs monoethyl glycol Water 300 1:2-aqueous solution of sodium chlorate (containing 1 part of chlorate to 2 parts of water 30 thickener I the frame or roller process. There then follows a steaming process under superatmc spheric pressure at 120-130 C., for the purposes of fixing the dye, and finallythere is A bluish .red shade is obtained which has the same qualities of fastness as those obtained in Example 2.

Example 7 an alkaline reducing treatment in the hot in a bath con- 5 On replacing the dyestuif used in Example 5 by the taining l to 2 g. per litre of an alkylphenol-ethylene oxide mixture of dyestuffs used in Example 3, a scarlet colour condensate. possessing good fastness is obtained.

On the polyester fabric there is obtained a bluish red E l 8 shade which has the fastness characteristic of the dyes 7 8 obtained by the processes of the preceding examples. 10 On replacing the dyestuff used in Example 6 by the Example 5 mixture of dyestuifs used in Example 4, a bluish red A fabric which has been previously desized is shade possessing excellent fastness 1s obtamed. foularded att a-bQFEhSOJ Cali? af tslrllspfensiolri containing 6 Example 9 ams'er reo e es 0 eorm a: gr p 1 y 6 parts of a condensation product of oleyl alcohol with OH O ethylene oxide is dissolved in 881 parts of water at 30'--35 l l C. and into this are introduced 100 parts of previously N=N 0 05115 degreased polyester fibre yarn on a bobbin.

The bath is circulated for some minutes and the fluid ()1 paste prepared with the following constituents is poured Parts dyestuII of formula:

IIIOZ 0H C0-NH N=N horns 0.5

dyestuff of formula:

orr CO-NH ONZN- v born 0.5

sodium methylene-dinaphthylsulphouate 2 mixture of water and denatured ethyl alcohol 10 Example 6 A Tergal fabric, previously desized, is foularded at about 50 C. in a bath containing 6 grams per litre of the dyestufi of the formula: I

(previously dispersed by means of twice its weight of sodium methylene-dinaphthylsulphonate) and 50 grams per litre of a condensation product of ethylene oxide with stearic acid. The fabric thus foularded is subjected to steaming for minutes under 1.8 to 2 kg. pressure and washed for 5 minutes at the boil in an alkaline reducing bath containing a non-ionic detergent.

The fabric thus foularded is passed on a evenly dyed.

The temperature is raised to 125 130 C. and kept at this for an hour. The polyester fibres are dyed a bright orange shade endowed with good general fastness; the bobbin having been completely penetrated, the fibre is v Example 10 The dyestuffs used in Example 9 are replaced by a mixture of the dyestuft of formula:

OH CO-NH 2 parts, previously dispersed, and of the dyestuif of formula: 1

2 parts, previously dispersed.

The polyester fibre is dyed a dark navy blue shade endowed with good general fastness, more particularly to sublimation.

Example 11 A dye bath is prepared with 881 parts of water at 30- 35 C. and 6 parts of cetyl-trimethyl ammonium bro mide, and parts of polyester fibre yarn are'introduced in the form of a crossed 'bobbin, previously degreased.

ace-ape? 4 The bathis circulated for. some minutes and a paste ,obtained by mixing the following components is added:

operating in accordance with the process of Example 4.

After printing, steaming and alkaline reducing treatment Parts dyestufi oi the formula:

sodium methylene-naphthylsulphonate ot-s mixture of water and denaturedalcohol- 2 The dyeing is eifected as in Example the polyester fiber is coloured a bluish red of great brilliance possessing good general fastness;

Example 12 p I On replacing the two dyestuffs used in Example 11 by the same quantities of the following dyestufis, previously dispersed:

a very bright reddish violetpossessing good general fastness isobtainedron polyester fibre.

Example 13 p A printing paste is prepared with the following'dyestu'fis:

under the same conditions, a red brown shade, having good general fastness, is obtained on polyester fabric.

We claim:

1. Process for the colouration of polyethylene terephthalate textile material which comprises printing a fabn'c made from the fibres with a printing paste containing an aqueous dispersion of a dyestuif on the general formula.

in which R represents a phenyl radical substituted by at least one member selected from the group consisting of hydrogen, halogen, .alkoxy, :nitro, cyano, phenyl amino,

:alkoxyphenylamino, land benzene azo group, and X represents an alkylgroup, and subjecting the treated fibres to steaming under superatmospheric pressure at a temperature betweenlQl" C. and C.

2. .Process,,:for the coloration ,of polyethyleneterephthalate textile material which comprises dyeing the fibres under super atmospheric pressure and at a temperature Parts 0H co-Nrr-G-m C1 I vNEH 9 about 100 C. with an aqueous dispersion of a dyestufi of the general formula:

in which R represents a phenyl radical substituted by at 10 least one member selected from the. group consisting of hydrogen, halogen, alkoxy, nitro, cyano, phenyl amino, alkoxy phenyl amino, and benzene azo group and X represents an alkyl group.

3. Process as claimed in claim 2 in which the temperature is between 101 C. and 150 C.

4. Process for the coloration of polyethylene terephthalate textile material which comprises foularding the fibres with an aqueous dispersion of a dyestufi of the general formula:

OH (JO-NEG 10 in which R represents a phenyl radical substituted by at least one member selected from the group consisting of hydrogen, halogen, alkoxy, nitro, cyano, phenyl amino, alkoxy phenyl amino, and benzene azo group and X rep resents an alkyl group and subjecting the treated fibres to a temperature between 150 C. and 200 C.

References Cited in the file of this patent UNITED STATES PATENTS OTHER REFERENCES J.S.D.C., Waters, December 1950, pp. 609-613.

Amer. Dyestufi Reporter, Zimmerman et 211., Apr. 25, 1955, pages P296-P30 2.

Man-Made Textiles, March 1956, pp. 72 and 74.

Du Pont Bulletin D-73, February 1956, pages 3-13,

Wilmington, Del.

Claims

1. PROCESS FOR THE COLOURATION OF POLYETHYLENE TEREPHTHALATE TEXTILE MATERIAL WHICH COMPRISES PRINTING A FABRIC MADE FROM THE FIBRES WITH A PRINTING PASTE CONTAINING AN AQUEOUS DISPERSION OF A DYESTUFF ON THE GENERAL FORMULA: