US3265459A - Dyeing textile material with vat and sulfur dyes - Google Patents

Dyeing textile material with vat and sulfur dyes Download PDF

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Publication number
US3265459A
US3265459A US322023A US32202363A US3265459A US 3265459 A US3265459 A US 3265459A US 322023 A US322023 A US 322023A US 32202363 A US32202363 A US 32202363A US 3265459 A US3265459 A US 3265459A
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dyeing
parts
vat
dye
sodium dithionite
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Schober Erhard
Janson Alfons
Schlueter Harald
Wilhelm Ernst
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BASF SE
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BASF SE
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/22—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using vat dyestuffs including indigo
    • D06P1/221—Reducing systems; Reducing catalysts

Definitions

  • This invention relates to a process for dyeing textile material with vat dyes and sulfur dyes comprising using as the reducing agent a mixture of sodium dithionite with a sulfinic acid derivative selected from the class consisting of a compound of the general formula:
  • A represents a member selected from the group consisting of hydrogen, low molecular weight alkyl and low molecular weight alkyl substituted by a radical of the general Formula III below
  • D represents the radical of a salt of Ian alkylsulfinic acid with 1 to 4 carbon atoms of the general formula (II) R1 where each of the radicals R stands for a member selected from the group consisting of hydrogen and alkyl and Z stands for a member selected from the group consisting of an ammonium cation and an alkali metal ion, said substituent of the low molecular weight alkyl designated by A above having the general formula agent in dyeing cellulosic textile material with vat. dyes.
  • the textile material may be dyed in different ways according to how it is made up.
  • hank yarn is dyed on equipment suitable for the purpose, as for example on cheeses and beams, and cloth is dyed according to the pad-jig process or by the pad-steam process.
  • Sodium dithionite has the advantage that it effects extremely rapid reduction of the vat dye, particularly :at high temperature, and therefore in some dyeing methods it makes possible an extremely short fixing time. This is important in continuous dyeing methods for piece goods,
  • sodium dithionite has the disadvantage that it is very easily oxidized by 3,265,459 Patented August 9, 1966 ICC atmospheric oxygen and that its stability in aqueous alkaline solution declines very rapidly with increasing temperature even in the absence of oxygen.
  • dyeing methods in which the dye liquor comes into contact with air or in which the alkaline dye liquor must be heated to elevated temperature for a long time it is therefore necessary to use an excess of sodium dithionite to compensate for the loss.
  • the very great reductive power of sodium dithionite may lead to excessive reduction and to destruction of the vat dye. There is a risk of this for example in the so-called high-temperature method in which package dyeing is carried out at temperat-ures higher than 90 C.
  • Dyeing at temperatures higher than 90 C. is known in package dyeing to have the advantage that goods which are difiicult to dye, for example those of mercerized cotton or linen, can be dyed satisfactory level shade-s even when using IN dyes, excellent penetration being achieved.
  • the high-temperature method it is usual to dye at final temperatures of about 115 C.
  • the use of the said reducing agents means that the air passage between the chemical pad and the steamer need not be so short as when using sodium dithionite because the stability of the said reducing agents to atmospheric oxygen is superior to that of sodium dithionite. It has however been found in this case, as in the case of other dyeing methods in which rapid vatting or revatting of the dye is desired, that the rate of decomposition of the said reducing agents at high temperatures is not always satisfactory. Thus for example when dyeing by the pad-steam method it is necessary to use a large amount of the said reducing agents and to effect steaming as far as possible at temperatures of about 110 C.
  • Suitable compounds of the general Formula I are for example the following:
  • each Z stands for a member selected from the group consisting of an ammonium cation and an alkali metal cation.
  • Such compounds are described in German patent specifications Nos. 1,071,042, 1,086,209 and 1,116,190.
  • Derivatives of ammonia of the said type may be obtained in various ways, for example by allowing to act on ammonia or on derivatives of ammonia bearing at least one hydrogen atom attached via nitrogen, alkali metal salts, such as sodium salts or potassium salts, or ammonium salts, of hydroxyalkylsulfinic acids having one to four carbon atoms which bear the hydroxyl group and the sulfinic acid group on the same carbon atom, for example the sodium salts, potassium salts or ammonium salts of hydroxymethanesulfinic acid, l-hydroxyethanesulfinic acid-(1), l-hydroxypropanesulfinic acid-(1), 2- hydroxypropanesulfinic acid-(2) or l-hydroxy-n-butanesulfinic acid-(1).
  • Alkali metal salts or ammonium salts of different hydroxyalkylsulfinic acids having one to four carbon atoms may be allowed to act simultaneously or successively in any sequence on ammonia or on derivatives of ammonia of the abovementioned type.
  • Compounds such as those described for example in German patent specification No. 1,071,653 may be used as alkali metal salts or ammonium salts of a hydroxyalkylsulfinic acid having two to four carbon atoms.
  • the sodium salts and potassium salts of hydnoxyethanesulfinic acid, hydroxy-n-propanesulfinic acid, hydroxy-isopropanesulfinic acid or hydroxy-n-butanesulfinic acid may be used.
  • the new reducing agent mixtures make possible a substantial decrease in the amount of reducing agent hitherto used. Moreover the new reducing agent mixtures bring about an increased stability of the reducing agent in the liquors which permits achieving readily reproducible results even under unfavorable working conditions. This advantage is particularly evident for example when working by the pad-steam method if the chemical liquor stands for a long period prior to use or if there is a long air passage between the chemical pad and the steamer. Furand thermore the dyeings obtainable according to the new process are distinguished from dyeings developed with sodium dithionite alone by improved levelness, higher brilliance and improved purity of shade.
  • the amount of the reducing agent mixture is such that the sodium dithionite concentration in the chemical liquor padded on is just sufficient for vatting the dye.
  • the second component of the reducing agent mixture then maintains the necessary redox potential during the steaming process. Since the sodium dithionite is practically completely used up during the steaming, the leuco compound of the dye is reoxidized in a very short time at the low temperatures prevailing in the rinsing bath. Rinsing out of the leuco compound is thus substantially prevented. A considerably better dye yield is therefore obtained than when dyeing with sodium dithionite alone, particularly when dyes having relatively low affinity are used.
  • the new reducing agent mixtures are used for dyeing by the high-temperature method they have the advantage that the dyeing process may be carried out without interruption and that the vat remains more stable at temperatures above 90 C. than when using sodium dithionite and aldehydes. A saving in reducing agents and more reliable operation during prolonged dyeing periods is made possible. Since all the additives may be added to the dye liquor at room temperature, dyeing may be fully automatic. Another advantage is that when using the high-temperature method, dye and reducing agent may be subsequently added in a simple way for the purpose of shading, because the new reducing agent mixture may be easily dosed. When working according to the process known from German patent specification No.
  • the reducing agent mixtures to be used according to this invention may be used both for batchwise and continuous dyeing with vat dyes and/ or sulfur dyes.
  • the relative proportions of the components in the reducing agent mixtures may be varied to achieve an optimum effect depending on the method of dyeing.
  • reducing agent mixtures which consist of about 40 to 80% by weight of sodium dithionite and about 60 to 20% by weight of .a compound of the general Formula 1 and/or an alkali metal salt or ammonium salt of a hydroxyalkylsulfinic acid having two to four carbon atoms.
  • lower proportions of sodium dithionite are usually chosen the higher the dyeing temperature is.
  • reducing agent mixtures consisting of about 20 to 80% by weight of sodium dithionite and about 80 to 20% by weight of the said sulfinic acid derivatives, the lower proportions within the said relative proportions being used the longer the periods of dyeing and development required.
  • D represents the radical of an alkali metal salt or ammonium salt of an alkylsulfinic acid having two to four carbon atoms.
  • D represents the radical of an alkali metal salt or ammonium salt of methanesulfinic acid.
  • Example 1 P-recleaned and bleached cotton poplin is padded at 25 C. in a commercial two-roll padding machine with '25 parts of the dye C.I. Vat Blue 6 Colour Index (1956) No. 69825) 975 parts of water 1000 parts.
  • the impregnated cloth is then given an'intermed-iate drying at C., padded in a commercial tworo11 pad at 25 C. with 55 parts of aqueous sodium hydroxide solution (38 B6.) 9 parts of sodium dithionite 6 parts of the compound having the formula:
  • a satisfactory dyeing, equally dyed at ends and sides, is obtained which is superior to a dyeing obtained by using sodium dithionite alone as the reducing agent.
  • the said method is also superior to the prior art method (according to which at least 27 parts of sodium dithionite is to be used for the present mixture) in that it requires a considerably smaller amount of reducing agent.
  • Example 2 Boiled cotton twill is padded at 25 C. in a commercial three-roll pad with 50 parts of the dye C.I. Vat Blue 20 (Colour Index (1956) No. 59800) 950 parts of water 1000 parts and then steamed for sixty seconds at 103 C. in a commercial steamer provided with a booster for the wet steam method.
  • C.I. Vat Blue 20 Cold Index (1956) No. 59800
  • the textile material is treated in the booster with a solution having the following composition:
  • the material is given a conventional aftertreatment. Penetration is very good. The dye yield is higher than when using sodium dithionite alone as the reducing agent in the development.
  • Example 3 Bleached shirt poplin is impregnated at 85 to 90 C. with 10 parts of the dye C.I. Vat Red 10 (Colour Index (1956) No. 67000) 40 parts of aqueous sodium hydroxide solution (38 B.) 7.5 parts of sodium dithionite parts of the compound having the formula given in Examples 1 and 2 937.5 parts of water 1000 parts.
  • the dyed material is immediately fixed for seven seconds in a hot liquid metal bath at 90 to 95 C. by the standfast method and then treated in a hot liquor which contains 20 parts of sodium sulfate in 1000 parts of water.
  • a uniformly dyed textile material is obtained having high brilliance of the shade.
  • Example 4 Uncleansed cotton tricot is treated at a liquor ratio of :1 on a commercial beam dyeing machine at 20 C. with a dye liquor having the following composition:
  • the temperature of the liquor . is raised from 20 to 115 C. within thirty minutes and dyeing continued at 115 C. for another thirty minutes.
  • the whole is then cooled to 70 C. and the dyeing finished off as usual.
  • a clear blue dyeing is obtained having good levelness.
  • Example 5 Grey cotton yarn is treated in cross-Wound form on a commercial high-temperature dyeing machine at a liquor ratio of 10:1 at 20 C. with a liquor having the following composition:
  • the liquor is heated to 115 C. within thirty minutes and dyeing continued for another sixty minutes at this temperature.
  • the liquor is then cooled and the dyeing is finished off as usual.
  • a uniform olive green dyeing fast to crocking is obtained. Penetration is very good.
  • Example 6 Viscose rayon on cheeses is treated on a commercial high-temperature dyeing machine at a liquid ratio of 15:1 at 40 C. with a liquor having the following composition: L
  • the temperature is raised from 40 C. to 115 C. within thirty minutes and dyeing continued for another thirty minutes at 115 C.
  • the material is then cooled and finished off as usual.
  • a very uniformly dyed material is obtained in which the points at which the threads cross are also dyed very uniformly. If dyeing is carried out by the conventional method in which temperatures of up to C. are used, the. points where the threads cross remain substantially white.
  • Dyeing is continued for forty-five minutes and the yarn finished off as usual. A dyeing having very good penetration is obtained.
  • Example 8 Unbleached cotton poplin is padded at room temperature in a commercial three-roll pad with 80 parts of aqueous sodium hydroxide solution (38 30 parts of the compound having the formula given in Example 4 10 parts of sodium dithionite 10 parts of the sodium salt of ethylene diaminotetracetic acid 870 parts of water at 25 C.
  • Example 9 Prebleached, mercen'zed cotton poplin is padded in a commercial two-roll pad at 25 C. with a liquor which has the following composition:
  • the dyeing is finished off as usual. A cloth dyed uniformly olive green is obtained. If in this case sodium dithionite be used as the sole reducing agent, it is found that at least parts thereof must be used.
  • a process for dyeing cellulosic textile material with a dye selected from the class consisting of vat dyes and sulfur dyes comprising using as the reducing agent a mixture which consists of to 80% by weight of sodium dithionite and 80 to 20% by weight of a sulfinic acid derivative selected from the class consisting of a compound of the general formula where x represents a whole number from- 0 to 2, y represents a whole number from 1 to 3, x-+y being equal to 3, A represents a member selected from the group consisting of hydrogen, low molecular weight alkyl and low molecular weight alkyl substituted by a radical of the general Formula III below, and D represents the radial of a salt of an alkylsulfinic acid with 1 to 4 carbon atoms of the general formula +-S0z Z R2 where each of the radicals R stands for a member selected from the group consisting of hydrogen and alkyl and Z stands for a member selected from the group consisting of an ammonium cation and an al
  • a process for dyeing cellulosic textile material with a dye selected from the class consisting of vat dyes and sulfur dyes comprising using as the reducing agent a mixture which consists of 40 to 80% by weight of sodium dithionite and 60 to 20% by weight of a sulfinic acid derivative selected from the class consisting of a compound of the general formula where x represents a whole number from 0 to 2, represents a whole number from 1 to 3, x+y being equal to 3, A represents a member selected from the group consisting of hydrogen, low molecular weight alkyl and low molecular weight alkyl substituted by a radical of a salt of an alkylsulfinic acid with 1 to 4 carbon atoms of the general formula where each of the radicals R stands for a member selected from the group consisting of hydrogen and alkyl and Z stands for a member selected from the group consisting of an ammonium cation and an alkali metal ion, said substituent of the low molecular Weight alkyl designated by Aabove
  • a process for dyeing cellulosic textile material with a dye selected from the class consisting of vat dyes and sulfur dyes comprising using as the reducing agent a mixture which consists of 20 to 80% by weight of sodium dithionite and 80 to 20% by weight of a compound of the formula where Z is a member selected from the group consisting of an ammonium cation and an alkali metal ion.
  • a process for dyeing cellulosic textile material with a dye selected from the class consisting of vat dyes and sulfur dyes comprising using as the reducing agent a mixture which consists of 40 to by weight of sodil 1 um dithionite and 60 to 20% by weight of a compound of the formula where Z is a member selected from the group consisting of an ammonium cation and an alkali metal cation.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
US322023A 1963-07-31 1963-11-07 Dyeing textile material with vat and sulfur dyes Expired - Lifetime US3265459A (en)

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US (1) US3265459A (de)
AT (1) AT252862B (de)
BE (1) BE651075A (de)
CH (2) CH410853A (de)
DE (1) DE1251715B (de)
FR (1) FR1455035A (de)
GB (1) GB1015626A (de)
NL (1) NL6408578A (de)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3839218A (en) * 1970-01-09 1974-10-01 Rohm & Haas Method of maintaining metal dithionite hydrate crystals in dispersible form
US3839217A (en) * 1970-01-09 1974-10-01 Rohm & Haas Stable, pourable alkali metal dithionite dispersion
US4113427A (en) * 1976-04-26 1978-09-12 Royce Chemical Company Process for dyeing cellulosic textiles with vat and sulfur dyes

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1759071A (en) * 1926-02-27 1930-05-20 Rohm & Haas Application of vat dyes to textile fibers
DE1025825B (de) * 1955-04-20 1958-03-13 Tno Verfahren zum Faerben von Textilien mit Kuepenfarbstoffen
DE1071653B (de) * 1958-06-04 1959-12-24 Badische Anilin- S. Soda-Fabrik Aktiengesellschaft, Ludwigshafen/Rhein Verfahren zum Färben von Textilgarnen mit Küpen- und/oder Schwefelfarbstoffen auf Garnoder Spritzfärbemaschinen
GB837940A (en) * 1958-07-29 1960-06-15 Basf Ag Improvements in printing textile materials with vat and sulphur dyestuffs
US2993743A (en) * 1961-07-25 i i ttts

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2993743A (en) * 1961-07-25 i i ttts
US1759071A (en) * 1926-02-27 1930-05-20 Rohm & Haas Application of vat dyes to textile fibers
DE1025825B (de) * 1955-04-20 1958-03-13 Tno Verfahren zum Faerben von Textilien mit Kuepenfarbstoffen
DE1071653B (de) * 1958-06-04 1959-12-24 Badische Anilin- S. Soda-Fabrik Aktiengesellschaft, Ludwigshafen/Rhein Verfahren zum Färben von Textilgarnen mit Küpen- und/oder Schwefelfarbstoffen auf Garnoder Spritzfärbemaschinen
GB837940A (en) * 1958-07-29 1960-06-15 Basf Ag Improvements in printing textile materials with vat and sulphur dyestuffs

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3839218A (en) * 1970-01-09 1974-10-01 Rohm & Haas Method of maintaining metal dithionite hydrate crystals in dispersible form
US3839217A (en) * 1970-01-09 1974-10-01 Rohm & Haas Stable, pourable alkali metal dithionite dispersion
US4113427A (en) * 1976-04-26 1978-09-12 Royce Chemical Company Process for dyeing cellulosic textiles with vat and sulfur dyes

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AT252862B (de) 1967-03-10
CH941964A4 (de) 1966-03-31
GB1015626A (en) 1966-01-05
DE1251715B (de) 1967-10-12
BE651075A (de) 1965-01-28
CH410853A (de) 1966-04-15
CH418293A (de) 1967-02-15
NL6408578A (de) 1965-02-01
FR1455035A (fr) 1966-04-01

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