DE1619604A1 - Process for dyeing textile fibers - Google Patents

Description

The invention relates to a method of dyeing of textile fibers or threads.

The method for dyeing textile fibers or threads according to the invention is particularly characterized in that an aqueous composition which comprises water and a dye which, per dye molecule, has at least one free thiosulfate group consisting of -SSO ₅ Na, -SSO ₅ K or SSO ₅ KH., contains on textile fibers of the group of cotton, regenerated cellulose, polyamide and polyacrylic, then a NapSp on the fibers. applying containing aqueous solution and washing the fibers with water.

At the time of the initial contact of the dye with the Na S ₂ -4 solution, the unfixed dye on the fiber is in the thiosulfate form, where, for example, each dye molecule has at least one free -SSO ₅ Na, -SSO ₅ K or -SSO ₅ NH, ^ - group per molecule of dye has "

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OBlGSNAL lHSPECfl »

It has been suggested in the art to use sodium sulfide or sodium cyanide to fix azo, anthraquinone, vat, Dioxazine - "* and metal phthalocyanine dyes with thio- To use sulfuric acid groups on cellulose fibers »

These known methods have a number of drawbacks and limitations, some of which are described _e Äachstehend

The handling of sodium cyanide and the resulting Runoff or drainage water especially excludes problems of high toxicity to humans and fish »Accordingly, it is altogether too dangerous a chemical for the practical technical use in a textile manufacturing or textile finishing plant.

Sodium sulfide provides when used in accordance with the above mentioned, known methods a number of difficulties. For example it must be used in conjunction with heat to effect the fixation, or when used at room temperature it must either be used in high concentration or in contact with the dye during TO. until 60 minutes remain to the

° To effect fixation, sodium sulfide adversely affects ο CO OO OJ

oo special to those of regenerated cellulose, what special

the softness and feel of cellulose fibers and lifting

- »■ applies if - *, s is used in conjunction with heat

or for a relatively long period of time with the

or when it is used in high concentration

Cellulose fibers remained in contact. Regenerated cellulose Swells on contact with strong NapS solutions, wodjrfufoh Repeated rewashing treatments required and also a stickiness when unwinding yarn from bobbins will. In addition, sodium sulfide is strongly alkaline and precipitates from water, especially from hard water insoluble materials off, these insoluble substances d-ie dyeing treatments interfere and require additional soap for their removal in the washing treatments.

Some azo dyes are particularly sensitive to it Sodium sulphide, in which the color value of the azo groups is destroyed and the color yield is reduced accordingly, when sodium sulfide is used, this being in particular The longer the sodium sulphide is used, the longer it is used at high concentrations or in combination with heat the dye remains in contact with sodium sulfide, the greater is the loss of color value.

There are two different types of azo dyes with free thioculphate groups, namely (1) those in which the thiosulphate group is directly bound to an aryl nucleus of the dye molecule, and (2) those in which a bridge member, e.g. an aliphatic or hydrocarbon radical which may be interrupted and substituted by hetero groups of the dye i inserted between the thiosulfate and the aryl nucleus? t _o

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BAD ORSGINAU

Sodium sulfide poses additional and "special" problems when used as a fixing agent for those azo dyes that have a free thiosulfate group directly on an aryl nucleus of the Contain dye molecule bound. The main problem is the color yield "

With many of the azo dyes that have at least one free thiosulfate group directly on the aryl nucleus of the dye molecule contained bound is the achievement of a high color yield using sodium sulfide as a fixing agent Impossible under any conditions because insufficient amount of the dye is fixed on the fibers or threads will. In addition, when fixing azo dyes with at least one free thiosulfate group which is bonded directly to an aryl nucleus of the dye molecule, a scarce and Specific amount of sodium sulfide to be used for each individual dye as andoo the color yield is lowered, slight increases or decreases the amount of sodium sulfide used to fix any given zo dye of the kind in which one If the free thiosulfate group is attached directly to an aryl nucleus of the dye molecule, the color yield can be considerable influence. This problem is compounded by the very large differences in the amounts of sodium sulfide used to fix various azo dyes with at least one free thiosulfate group that is directly attached to an aryl group of / Dye molecule is bound, made difficult; for example

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_ 5 -

Such a fizo dye can contain 12 times as much sodium sulfide as another such dye in order to achieve a technically acceptable color yield ", Obviously, is the search for optimal sodium sulfide concentrations of Fixing baths and changing these concentrations for individual dyes are a time consuming and costly burden the few dyers who dye with many different colors, want to adopt, to achieve a desired shade or tint, it is often necessary to use two or more azo dyes to mix, each of which has at least one free 3? hiosulfate group per dye molecule on the aryl nucleus of the dye has bound, and being used to fix each dye required amount of sodium sulphide is considerably different ο In such cases a full color fixation of both dyes can be achieved with sodium sulfide,

The above drawbacks and limitations of the known operation are overcome by the method according to the invention overcome, while at the same time further advantages, such as after- » executed standing up, created.

S ₃ ι is less dangerous and iacic than sodium cyanide

In the G-egensata to Natriümsulfid there is no need for the use of Na ^ Sp _-. ^, In order to achieve a color fixing i ⁿ combination with ¥ ä) irme and it is an excellent color fixation at room temperature Bs is also obtained

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there is no need to use the Na ₃ S ₂ in high concentration or to keep the NapSp * in contact with the dye for a considerable time in order to achieve fixation.

A surprising feature of the invention is to be found in it see »that the fixation of the dye at" room temperature and obtained at a very low NagSg ^ concentration can be * being the dye and NagiU * no longer than 1 to 6 seconds are in contact with each other »So is the method according to the invention "BigoMars for use high speed with modern dyeing equipment » for example continuous dyeing machines (padding ranges) very valuable * NagSg i can also be used to fix a lower level of alkalinity than obtained with sodium sulphide, resulting in a softer and improved handle of cellulose— fibers and also good for lower precipitation of insoluble ones Materials derived from water *,

Übeirä§6hihd§r way MöiineäeH Ääöfärbstoffe with a directly bound to an-ii aryl core of the dyestuff moiekül, free Thiosülfätgrüppe with a lower by about 2/3 Weight amount of NägSg ^ »can be fixed as SfägS.

The fact that the fixation at room temperature, without any need for high Ή3.2Β2_, Λ- ^ οηζβη ± τΒ.Ι ± οηβη or prolonged mixing times between the polysulfide and the azo dyes, can be errsiokt, leads to less

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Loss of color value of the sensitive azo groups and an improved color yield, and in some cases, too an improved brightness or luminosity of the shade over sodium sulfide.

The improvement in color yield is particularly noticeable when dyeing azo dyes with at least one free thiosulfate group bonded directly to an aryl group of the dye molecule. For many of these dyes, the color yield is 20 to 1005% higher when using Se ^ ^ ^a 2 ^ 2-4 ^a ^ ^s ^ ^e ^ Using the optimal sodium sulfide concentration.

Another surprising and very advantageous feature of the invention is based on the fact that the optimal concentration of Na ₂ S _2- . to fix azo dyes with at least one free thiosulfate group which is bonded directly to an aryl nucleus of the dye, and to achieve a high color yield, extends over a much larger area than sodium sulfide ^ K and that accordingly the color yield by small changes in the Na ₃ S ₂ ^ concentration, in contrast to sodium sulfide, is not adversely affected. Moreover, there is only a slight difference in ink between the optimal Na ₂ Sp_j concentration for the fixation of a dye of the type indicated above and another type, which is in complete contrast to sodium sulfide. Standard fixation solutions of: Na ₃ Sk. in textile

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Every time a finishing plant is used without the need to change the concentration when a different dye is used. A better yield can also be obtained in dye mixtures of certain azo dyes with Ha ₂ Sp _- J than with lapS.

After all, this system is more economical, since ⁷ * ^a 2 ^S 2-4 costs less than Na ₂ S and less Ia ₂ S ₂ j than HapS is required, and it also saves soap, time, and heat.

Sas method according to the invention can be used for dyeing or Printing of textile fibers or threads made of cotton, regenerated Celluloe, Polyauid and Polyacryl are applied · The Textile fibers or threads can be in any desired Form, e.g. textile goods or tuoh, yarn, ball of chain, non-woven Textile goods, raw material or the like are present.

Examples of dyes include can be fixed after the Terfahr & n E _r according to the invention azo, sulfuric, phthalocyanine, MotalphthalocyanÜn-, perylene, dioxazine, anthraquinone, and vat dyes Dibenzanthronfarbetoffe ₉ which further through the Content of at least one free * hiosulfate group, consisting of -SSOvNa. -SSOJK and _o -SSO ₅ SH ^ per molecule of dye are marked.

The dye can au £ the fibers in any go-O ₀ wished, be applied, for example by dyeing on

- »the jigger, duroh padding, tub dyeing (beck), by means of co

Pressure rollers or the like. The dyes used

amount depends on the desired depth of shading or

Tint abο

In addition ζιί dye and water can, the dye or the dye bath optionally any additives, such as inorganic electrolytes to increase the adsorption of the dye on the fiber, leveling agents, such as sodium alginate, penetration or dyeing aids, such as anionic and non-ionic, surface-active agents, alkalis ,, thiourea or the like "and common in the case of printing pastes gums, thickening agents, emulsifying agents od _e like. contain" urea,

After the dye has been applied, the fibers can or threads for a while at room temperature or in a closed, with respect to humidity and temperature

Treated in a controlled chamber, swabbed, steamed / dried to facilitate the binding of the dye into the fibers.

The term IfepSp α used here refers to a sodium polysulphide or to mixtures of sodium polysulphides, e.g. disodium disulphide or disodium trisulphide or disodium tetrasulphide or to mixtures of eiae »7> any two or three of these polysulphides, in the case of mixtures the index expression added to the S atom is 2- 4 not necessarily an integer »Sodium polysulphides are well known and

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- ίο -

are made by having a sulfur flower hot aqueous solution of sodium sulfide is added.

Sulfur is formed from the highly concentrated make-up solutions of sodium tetrasulfide on prolonged exposure precipitated in air and this can be done by adding 5 ßew.-ji Carbitol to the concentrated preparation or standard solutions can be prevented, these stock or batch solutions subsequently used in the preparation of the fixing solutions can be.

The unfixed dye in thiosulfate salt form containing fibers are then with the aqueous NagSp. solution, for example by dipping the fibers into the fixing solution The time of contact with the fixing solution should be wet or dry

The fixing solution comprises an aqueous solution of _32. The amount of NapSp. That is used relates to the amount of dye that is to be fixed, approximately 0.07 to 0.64 g of NapSp. and preferably about 0.214 g of NapS ^ for every g of dye to be fixed can be applied to the fibers. The fixing solution can also optionally comprise a simple water-soluble inorganic electrolyte, no tend to prevent. Approximately 25 to 300 g NaGl per 1 fixative solution

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suitable for this purpose. The Na ₂ Sp _- λ is applied in the form of an aqueous solution to the fibers or threads and can be applied according to the pad-nip process, by spraying or spraying, dipping the fibers into the solution or can be applied by any other conventional method. An expedient and illustrative method is to pass the fibers containing the unfixed dye thereon through a block chassis in which about 1 to 10 g Na ₂ S _2-4 contain 1 fixing solution for every 1% by weight of the dye on the fibers is to lead _; and squeezing the fibers or filaments between rubber-coated pressure rollers, allowing a moisture absorption of 60 $ fixing solution, based on the weight of the water. The dye fixation is very rapid and in many cases can be viewed as immediate. In most cases the fixation is complete when the dye and Na ₂ S ₂ * have been in contact with one another for about 1 to 30 seconds.

After contact with Na ₂ Sp _- *, the fibers are washed with water, which can be at room temperature. The water is used to remove residues of folysulfide salt and other water-soluble residues from the fibers. If desired, the fibers can optionally by air, water.

steam or saline solution before washing »

can. Subsequently, the viasäes the fibers

rinsed and dried in the usual way.

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Dyeings and prints with excellent color yield W * # Wash fastness properties result from the process described above.

The e _r-making is apparent in the following examples further explained, in which the parts listed by weight unless other specified _e

example 1

On mercerized cotton goods weighing

Ο **** 2 /
112 g each about 1 ^ 19- m (fsquare yard) becomes one color barrel

padded, which consists of 25 g of the dye compound NaO ₅ SS-

there is 1 liter of water at around 49 ° C (120 ° »). D ± _e textile product is squeezed off while maintaining a wet pick-up of $ 60, based on the weight of the product, (the product contains 0.015 g of dye, calculated as solid, of 1 g product).. The textile material is dried and padded with an aqueous fixing solution of 6.05 g Na ^ S and 200 g NaCl per liter at room temperature; The textile product is squeezed while maintaining a moisture absorption of 60 $, based on Huf the "material weight, whereby the fabric or din textile product Γ,-14 P. Nn. ^ p. 1 f F - v \. fabric contains. The üfH / ei ';' -. 'i rd with * ab. ^c 5er at Raunteir.r er ^: door _t -r ₍ .waschen

0 "9 8 ^ 8/1 9 0 3 BAD ORIGiNAt

~ 13 -

■ Sine bright yellow color with excellent - fastness to washing is preserved «,

If desired, the NH, - or K salt of the above indicated dye can be used for the dye used in this example.

• The color yield in the above coloring is at least twice as large as that using NapS available as a fixative »

Examples 2 to 46

In those listed in the table below example on cotton, Viskosekunstseidle-, polyamide or Polyacryltextilware an aqueous paint composition consisting of 25 of the indicated in the second column, the dyestuff g per 1 1 of water at about 6O ⁰ C (HO ⁰ F) padded, after which the fabric to an uptake of 0.015 g of dye (calculated as dry solids) per 1 g of textile goods is squeezed off. The fabric or the goods are pre-dried in an open width with infrared units to a moisture content of about 10 $ and then essentially to the dry state in the open width in a Winem drying frame, which is mounted in a housing and at about 177 ^ 0 (35O ⁰ F) heated is (Housed tenter frame) dried, "the fabric is treated with steam for about 2 minutes at about 11O ⁰ C (230 ⁰ F) in an air-free damper, then with a solution of 4.537 g of the polysulfide shown in column 3 and 200 ^ JTaGl; 1 1 water padded at hem temperature,

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-H-

^w else squeezed in that it £ "specified in column 4 in g of polysulfides, which is indicated in the third column (berechtet as dry solids) per 1 g of the on the fiber material present ^ dye added iafh, t" then passed through block tubs which are provided with output pinch rollers and contain water at room temperature for 15 seconds, treated with soap, washed with water and dried.

As can be seen, the Na atoms of the free thiosulphate groups are trapped of the dyes shown in the second column by K or HH. be replaced.

Tabel

example
No. dye Poly-
sulfide ng 0, 20th - colour 2 Dye from Example 1 Na ₂ S ₂ 0, 27 yellow 3 Il It Na ₂ S ₃ 0, 15th η 4th Il ti Na ₂ S3.5 η 5: Sodium salt of the by. Coupling

from equimolar amounts of diazotized 3-amino-benzylthio-sulfuric acid and 2- (2 ·, 3 ^f -hydroxynaphthoylamino) -benzylthiosulphuric acid obtained

fabric

6 »

7 «

Na ₂ S ₂ 0, 30th H Na ₂ S ₃ O, 21 H Na ₂ S, O, 15th

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Example no.

Table (continued)

Dye polysulphide g color

Sodium salt of the diazotized by coupling 1 mol! Sodium S-4-aminophenylthiosulfate and 1 mole of 8-amino-2-naphthol and ' coupling equimolar amounts of the product thereof and diazotized! Sodium S-4-aciinophenylthioeulfate obtained dye

Solubilized sodium salt of C.I. it is sulfur green (CI. No. 53572)

Sodium salt of the dye obtained by condensation of 1 mole of phthalocyanine- dilulfonyl chloride and 2 moles of sodium S-4-amino phenylthiosulfate

_{Sodium salt of the dye Na 2} S ₅ obtained by the condensation of 1 mol of copper phthalocyanine trisulfonyl chloride and KoI sodium S-4-a-phenyl thiosalfate

^Na 2. ^S 4

0.30 black

Na ₂ S ₅ 0.25 ti Na ₂ S ₄ - 0.15 Il Na ₂ S ₂ 0.20 green Na ₂ S ₅ 0.15 Il Na ₂ S ₄ 0.30 Il Na ₀ S ₀ 0.17 turquoise

Na ₂ S ₅ 0 , 22 η Na ₂ S ₄ 0 , 30 It Na ₀ S ₀ Q »15 Turk

BATHROOM OP,! GSMAt

0 9 8 3 3/1983

example

Table (continued ) dye

Polysulfide g

colour

Sodium j ^ az of the dye obtained by condensation Na ₂ S ₂ 0.24 turquoise tion of 1 mole of nickel phthalocyanine nitride sulfonyl chloride with 3 moles of sodium S- (2-aminoethyl) -tniosulfate

ti It

SOoNHCH ₂ CH ₂ SSO, Na

Na ₂ S ₃ 0 > 30th ti Na ₂ S ₄ 0 » 15th ti Na ₂ S ₂ 0 » 15th Red

NaO ₃ SSGH ₂ GH ₂ NHSO ₂

Il Il

Na ₂ S ₄

H _t

9 A

he κ

01-

0.26 "0.22"

0.29 blue

(SO ₉ KHCH ₉ GH ₉ SSO ^ Na)

₂ GH ₂

T-,

0.24
0.15 "

003 8 38 / 19.8 3-

BAO

Table (continued)

At- '
game
No. dye NH-CH
I. 3 Poly-
sulfide 0, 24 colour 29 0 Na ₂ S ₂ blue V
M-CH OH
2-CH-CH ₂ -SSO ₅ Na Il
0 Il 0, 30th 30th Il Il Il Na ₂ S ₅ 0, 15th Il 31 Il Il Sodium salt of duiiohSlfms e tnion Na ₂ S ₄ 0, 16 Il 32 blue

of 1 mole of disulfonyl chloride of isodibenzanthrone and 2 moles of sodium 8- (2-aminoethyl) thiosulfate obtained dye

N = N-

SQ ₂ NCH ₃ CH ₉

CH ₂ SSO ₅ Na

Il Il

It Il

Il Il

Na ₂ S ₅

Na ₂ S ₄

0.19 0.30

-SO

2Ϊ2 ^Η 3

, ^l 2

CH ₂

SSO ₅ Na

-OH

Well ₂ S ₂ ο, 22nd orange Well ₂ S ₂ ο, 20th tr Well ^ β / 0. 18th ti

0 098 38/1983

Table (continued)

Example Poly-No dye sulfide g yarbe

38. Gd-NH-CH ₂ -CH ₂ -SSO ₃ Na Na ₂ S ₂ 0.15 yellow

Il Π i '.1-SO ₉ -NH-CH ₀ -CH ₉ -SSO ^ ITa

Il SO ₂ -NH-CH 2-CH ₂ -SSO ₃ Na Na ₂ S ₃ , 5 0, 30th 39 Il Il • ι Na ₂ S ο, 20th 40 It H

S0 ₉ N (CH,) CH _o CH ₉ SS0, Na ⁴¹ 1

Na ₂ S ₂ 0.17 red

~ ^OCH 2 ^CH 2 ^SSO 3 ^Na

42 "» "Na ₂ S ₃ 0.19

43 """ ^Na 2 ^S 4 °» ²⁶

44 Sodium salt of the _{dye obtained by condensation Na 3} S ₃ 0.30 blue tion of copper phthalocyanine trisulfonyl chloride (1 mol) with 3 mol of sodium S- (4-aminobenzyl) sulfate

45 """Na ₂ S ₅ 0.24"

46 """Na ₂ S ₄ 0.15"

00983 8/1983

Example 47

A paste of 2.5% by weight is applied to a cotton fabric. a compound of the formula

OH
NaO ₃ SS- / ^ V

1.75 wt .-% etherified Lokustbohen gum, 1 wt .-% emulsifier, 40 GeWc-% ^II ¥ arsol "mineral oil solvent and 54.75 wt .-% water printed. The textile product is dried with" .Vapor at about Treated 10C ° C (214 ° F) for 30 seconds, padded with Λ% Na ^ S, and 20% NaCl in a warm solution at room temperature, squeezed off, rinsed with water, treated with soap, rinsed with water and dried. A yellow print with excellent fade resistance and good color value is obtained.

Example 46

On a cotton textile product weighing 112 e: ^ e 0.836 m (square yard) becomes a paint mass of 12.5 pounds dex link

ÜH? ^ P OH

O / C-C-K-N- / V /> -K-K-C-Cv / -ν - :; ] ■ U V = / I > - /> - ssc iia Μϊ-c-CE, ch, -c = k / V = / ^

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, each 1 1 of water padded at about 49 ° C (120 ⁰ F ¹ ). The textile material is squeezed out to a moisture absorption of 60%, so that 0.0.075 g of dye, calculated as solids, remain per 1 g of textile goods. The textile product is then immersed for 30 seconds in a solution of 0.375 S NaρS ^, 1 liter of water at a ratio of liquid to textile material of 10: 1, treated with soap with water / at room temperature for 5 minutes, treated with soap Rinsed with water and dried. A bright orange-red coloration was obtained.

Example 49

An aqueous one containing the 1: 1 chromium complex of the compound the formula below

-SS0, well

is padded onto a cotton fabric, and so pressed or absequetrciit that 1.5 P "were deposited dye per 100 g cotton Dac material is dried and a Lc;. -ur.r> of '-, 86 g-KAPG _a and? G0 < ^T NaCl per 1 '. Vasser at Ii yum *;' ■ ·: /; -rbtur Ruf pumped, squeezed off under the addition of "iiriltuii ^ cir. " -. R Feuclitigkeitsaufnähme of 60%, nit "." Ascer r '-Gj / Jlt, gerifir.ij * and dried, producing a bright color.

009838/1983 ^ ⁰ ^

1619804

~ 21 -

Almost twice the amount of Na ₂ S as that of MapS ^ is required to obtain a somewhat lower color yield and a reduced brightness or luminosity.

Example 50

A color composition is padded onto a cotton corduroy fabric, which consists of 10 g of the sodium salt of the dye, which results from the Condensation of a mole of

GuPc-c

and 2.3 moles of the sodium S-4- <3tairiophene; ylthiosulfate gives, and 7 g of the sodium salt from GI ₀ Solubilized Sulfur Green (GoI ₀ Nr ₀ 53 572) and 15 g of a compound of the formula

each 1 1 of water at about 54 ° G (130 ⁰ I ¹ ) consists. The material is dried, then padded with an aqueous solution of 6 g Na ₂ S ^, and 200 g NaGl per 1 water at room temperature, squeezed off while maintaining a moisture absorption of 60% _}

009838/1983

Rinsed with water, treated with soap, rinsed and dried. A green color is obtained "

Example 5 * 1
An aqueous composition containing 25 g

CE,

1 y

C = O
NaO, SS- «'> -NH-CH

^ c = o

KH

per 1 1 of water at about 49 ° C (120 ⁰ F) is padded onto a cotton fabric and so abgequetzscht that the textile material has an amount of 0.0 to 15? Retains dye per g of fabric, whereupon the textile product is dried. The material is then padded with a solution containing 1.9 P Na-S ^, and 200 g NaCl per liter of water at room temperature, and squeezed off except for an uptake of 0.07 g NapS ^, per g dye. The textile material is then rinsed with water, treated with Seijie, rinsed and dried _o is obtained a bright and bright yellow coloration with excellent color yield and resistance to washing properties.

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Example 52

The procedure described in Example 51 is repeated with the modification that the quantities of Na-S ^, per liter from 1j9 | T to 10 p; is increased and that the amount of Na ₀ S ^ absorbed per g of dye is increased from 0.07 g to 0.64 κ.

BAD 009838/1983

Claims (1)

Claims 1. A method for dyeing textile fibers, characterized in that that you get an aqueous composition of water and one dye, the Qe dye molecule at least a free ThioHulfatgruppe, 'consisting of -SEO-zNa, -SSCUK or SSO ^ NIL ·, on textile fibers made of cotton, applies regenerated cellulose, polyamide or polyacrylic, whereupon an aqueous solution of NapSp ^ is applied to the textile fiber material and then the fiber material with V / ater is washed. ' 2 «Method according to claim 1, characterized in that one about 0.07 to 0.64 g of I ^^ Sp ^^ on da-ε fiber material each 1 g of dye applied to the fibers «. 3β method n ⁿ ch claim 1 or 2, characterized in that. that the ütextilfasermaterial is treated with an aqueous composition which contains as dye an azo, sulfur, phthalocyanine, metal phthalocyanine _T , perylene, dioxazine, anthraquinone, vat or dibenzaiithron dye with at least one free thiosulfate group per dye molecule ^. BATH 0 0 9838/1983 4-a method according to one of claims 1 to 3, characterized characterized in that the IT dye on the JPaser with an aqueous NäpSp ^ .- solution, which also contains NaGl contains, pinned 009838/1983