US3816069A - Coloring cellulose textile material with a cellulose{14 reactive dye - Google Patents

Coloring cellulose textile material with a cellulose{14 reactive dye Download PDF

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US3816069A
US3816069A US00225435A US22543572A US3816069A US 3816069 A US3816069 A US 3816069A US 00225435 A US00225435 A US 00225435A US 22543572 A US22543572 A US 22543572A US 3816069 A US3816069 A US 3816069A
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cellulose
dyestuff
reactive
water
dye
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US00225435A
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English (en)
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H Andrew
W Anderson
W Marshall
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Imperial Chemical Industries Ltd
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Imperial Chemical Industries Ltd
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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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose
    • D06P3/66—Natural or regenerated cellulose using reactive dyes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/918—Cellulose textile

Definitions

  • ABSTRACT A process for colouring cellulose textile materials by impregnating the material with a water-soluble dye containing a cellulose-reactive group and fixing the dye on the material by treatment with an alkali applied in the dyebath or a separate bath in an amount conventionally used for that alkali for fixation of cellulose-reactive dyes, characterised in that the dyestuff used exhibits the following percentage exhaustions at different saline concentrations when dyed on to cotton or viscose rayon for 60 minutes at a strength of 0.5-1 .0%, based on the weight of material being dyed, a liquor-to-goods ratio of :1 and a temperature of 80 C: g/] sodium chloride 0 2O 80 100 120 ex- .thaustion O-15 40-80 55-86 -90 71-94 75-96 78-97 and that the material is subjected after fixation of the dye to at most a rinse in water to
  • the class of dyestuffs suitable for use in the new dyecapable in the presence of an alkaline substance of reing process are those whose exhaustion on to cotton acting with the hydroxyl groups of cellulose so that the i5 and viscose rayon fibres when applied in this manner dyestuff, or the remainder of the dyestuff after splitting fall between the lines A and B of the drawing attached off of this atom or group, becomes covalently linked to to this specification.
  • the cellulose molecule As can be seen from the drawing, the cellulose molecule.
  • Dyestuff attached to the celluthe dyestuff used within exhaustion curve limits A and lose in this manner is far more resistant to washing than B, exhibits the following percentage exhaustion for the the water-soluble direct dyes previously used but the following saline concentrations:
  • cellulose-reactive dyestuffs must in contrast, direct dyes are usually finished off after contain an atom or group capable of reacting with the the colouring process by a rinse with warm water and hydroxyl groups of cellulose so that the dyestuff or its optionally a simple after treatment with a cationic residue become covalently linked to the cellulose moleagent or metallic salt to remove dyebath additives and cule.
  • a large number of substituents containing such possibly a little dyestuff loosely attached to the surface groups are known from the literature on this subject, of the material being coloured.
  • a,B-unsaturated acyl radicals class of reactive dyestuffs for which the customary or aliphatic carboxylic acids for example, acrylic acid, scouring process can be dispensed With but yet g a-chloro-acrylic acid, propiolic acid, maleic acid and dyeings which are only slightly lower in fastness to monoand dichloro-maleic acids; also the acyl radicals washing and other wet treatments than commercially of acids which contain a substituent which reacts with available react dye but have a much higher h cellulose or polyamides in the presence of an alkali, e.
  • dyes Offer a cha ae the radical of a halogenated aliphatic acid such as chlochange of substantivity in saline solutions of different roacetic acid, B-hl0roand B-bromo-propionic acids strengths when applied under the conditions defined a d a,fl-dihloroand dibromo-propionic a ids Oth r hereafter.
  • a halogenated aliphatic acid such as chlochange of substantivity in saline solutions of different roacetic acid, B-hl0roand B-bromo-propionic acids strengths when applied under the conditions defined a d a,fl-dihloroand dibromo-propionic a ids Oth r hereafter.
  • test conditions USCdlO define whether or examples of cellulose or p lyamide-reactlve groups are not a dyestuff is iuitablle are afsgos lol -f h d tetrafluorocyclobutane carbonyl, trifiuorocyclobutene 5 ml Portions 0 a $0 Uilon 0 g 0 t 8 P y carbonyl, tetrafluorocyclobutylethenyl carbonyl, trilfl 100 ml 0f distilled water are dllUllCCl according to the fluorocyclobuteneethenyl carbonyl, and heterocyclic following table: radicals which contain 2 or 3 nitrogen atoms in the heterocyclic ring and at least one celluloseor polyamidereactive substituent on a carbon atom of the ring.
  • s-triazin-Z-yl and pyrimidin-2-yl or 4-yl radicals which contain an at least one of the remaining 2-, 4- and 6-positions, a bromine or, preferably, a chlorine atom, a sulphonic acid group, a thiocyanato group, an aryloxy or arylthio group containing an electronegative substituent such as sulphophenoxy, sulphophenylthio, nitrosulphophenoxy, disulphophenoxy and sulphonaphthoxy, or a group of the formula:
  • Y represents a group of atoms necessary to form a or 6-membered heterocyclic ring which may carry substituents or form part of a fused ring system; or a quaternary ammonium e.g. pyridinium group; or a group of the formula:
  • R and R each represent the same or different alkyl, cycloalkyl, aryl or aralkyl group, or R and R together form, together with the nitrogen atom, a 5- or 6-membered heterocyclic ring; or a group of the formula:
  • R and R may be the same or different and each represents a hydrogen atom or an alkyl, aryl or aralkyl group.
  • the said ring may have a non-reactive substituent on the remaining carbon atoms.
  • non-reactive substituent there is meant a group which is bound by a covalent bond to a carbon atom of the triazine or pyrimidine nucleus, which covalent bond is not ruptured under the conditions used for application of the reactive dye.
  • substituents there may be mentioned, for example, primary amino and hydroxyl groups, also monoor disubstituted amino groups, etherified hydroxyl and etherified mercapto groups; in the case of substituted amino groups, this class includes, for example, monoand di-alkylamino groups in which the alkyl groups preferably contain at most 4 carbon atoms, and which may also contain substituents for example.
  • this class includes, for example, alkoxy and alkylthio groups preferably those of low molecular weight, i.e. having up to 4 carbon atoms and phenoxy, phenylthio, naphthoxy or naphthylthio groups; as particular examples of all these classes there may be mentioned for example:
  • Chlorine atoms or cyano, nitro, carboxy and carbalkoxy groups in the 5-position of a pyrimidyl radical come into the category of non-reactive substituents.
  • Textile materials which may be dyed by the new process include cotton, viscose rayon, including polynosic and high wet modulus regenerated cellulose, linen and other essentially cellulosic fibres in the form of loose fibres, slivers, yarns, threads, woven, knitted, braided or otherwise interlaced, or unwoven sheet materials, also blends of these fibres with themselves or other materials, e.g. wool, nylon, polyester, acetate or acrylic materials.
  • the dyestuff and alkali be applied to the textile ma terial from a single vessel since it is possible, for example, to impregnate the fabric witha solution of the dyestuff and, with or without an intermediate drying step, thereafter impregnate the material with an alkaline solution, so that only after the second impregnation is the treatment with the dyestuff carried out in the presence of aqueous alkali.
  • Typical methods of application include e.g.: (a) The material may be dyed in the beck, winch or circulatory dyeing machine or on the jig in an aqueous saline solution of dyestuff, the alkali being present from the start or added in one or more portions after a period of time when a part of the dyestuff present has been absorbed by the material.
  • This method is primarily suitable for use with liquor to goods ratios of from 5:1 to 30:1 although ratios outside these limits can be used if desired.
  • salts which may be used to make up the saline dyebath, there may be mentioned sodium chloride and sodium sulphate. Salt concentrations of 30 g per litre to g per litre are those most commonly used.
  • alkali metal hydroxides silicates, phosphates, carbonates and bicarbonates
  • the alkali used and the temperature of dyeing may need to be chosen to conform with the cellulose-reactive grouping present in the dye- Reactive group stuff.
  • Typical recommendations are as follows:
  • a further method of application comprises padding the material in a dyestuff solution, preferably containing a migration inhibitor, e.g. an alkyl naphthalene sulphonate, a mild oxidising agent e.g. sodium m-nitrobenzene sulphonate, and if necessary, a solubilising agent e.g.
  • a migration inhibitor e.g. an alkyl naphthalene sulphonate
  • a mild oxidising agent e.g. sodium m-nitrobenzene sulphonate
  • solubilising agent e.g.
  • immersion of the material in a saline alkaline solution can be carried out e.g. by padding in which case the material may be heated with infra-red heaters, baked or steamed for a short period of time to accelerate the reaction between the dyestuff and the cellulose;
  • a further method of application comprises padding the material in a dyestuff solution containing the alkali and thereafter heating or steaming as in (b) or wrapping the material in a cover to prevent evaporation and storing the material in a moist condition for a number of hours to effect reaction between the dyestuff and the cellulose. ln this method it is frequently customary to use a stronger alkali than in the methods described under (a).
  • sodium carbonate may be used with dichlorotriazine dyes, a reaction time of 2 hours being usual, whilst dyes containing a group of lower reactivity may be fixed using a caustic alkali or trisodium phosphate and reaction times of 24 hours or longer.
  • the dyeing process differs from those commonly used for application of reactive dyestuffs by omission of the usual scouring step and from those commonly used for application of direct dyes by the concentrations of salt and alkali present in the dye solution.
  • EXAMPLE 1 2,000 parts of water containing 120 parts of salt are heated to C and parts of cotton yarn are added, followed by 2 parts of dyestuff (l) of the Table dissolved in a small amount of water. The yarn is agitated in the dye liquor at 80 C for 30 minutes then 40 parts of sodium carbonate are added and dyeing is continued at 80 C for a further 60 minutes.
  • the yarn is then removed from the liquor and rinsed in cold water until the rinsing water runs clear. It is dyed in a red shade.
  • EXAMPLE 2 500 parts of water containing 50 parts of salt are heated to 85 C and 4 parts of dyestuff (2) of the Table are added. 100 parts of viscose rayon piece are added and, after 30 minutes, 10 parts of sodium carbonate are added. After a further 60 minutes, the rayon is removed from the dye liquor and rinsed in water at 3035 C until the rinsings are clear.
  • the viscose rayon is coloured a deep golden yellow shade.
  • EXAMPLE 3 Indian head cotton cloth is padded at 75% expression in a dye liquor containing 13.6 parts of dyestuff (5) of Table l 150 parts of urea 1 1.25 parts of sodium carbonate 1.5 parts of a wetting agent and water to 750 parts. The cloth is dried for 3 minutes at 1 C and baked at 150 C for a further 3 minutes, then given a rinse in cold water.
  • the cloth is dyed an orange shade.
  • EXAMPLE 5 Spun viscose rayon piece is padded at expression in a dye liquor containing 27.0 parts of dyestuff (6) of Table l 7.5 parts of sodium carbonate 1.5 parts of a wetting agent and water to 750 parts. The cloth is dried at 1 10 C for 3 minutes and steamed at l00-120 C for 5 minutes, then rinsed in cold water.
  • The'cloth is dyed an orange shade.
  • EXAMPLE 6 lndian'head cotton cloth is padded to 75% expression in a dye liquor containing 16.5 parts of dyestuff (4) in Table l 1.5 parts of a wetting agent and water to 750 parts. The cloth is dried for 3 minutes at 1 10 C and further padded in a liquor containing 10 parts of caustic soda 300 parts of salt and water to 1,000 parts. The cloth is steamed, without drying, at -120 C for 1 minute, then rinsed in cold water.
  • the cloth is dyed a deep golden yellow shade.
  • Table 1 describes the mode of preparing of a number of dyestuffs which can be used in the new process, together with the shade of the resultant dyeings.
  • rams I Condense 2.4-dichloro-6-aminos-triazine Red with 1 mole of 6-amino-2-(4-phenylazophenylazo)-l-naphthol-2,3,4-trisulphonic acid Condense cyanuric chloride with 1 mole of Golden 4'-nitro-4-( 4 -amino-2"-methylphenylazo )stilbeneyellow 2,2-disulphonic acid and 2 moles of the product with l.4-diaminobenzene-Z-sulphonic acid 3. As for 2. but use benzidine-2,2-disulphonic do.
  • Table II gives the results of the test described earlier TABLE IV for these dyestuffs, at the various concentrations of. brine, expressed as a percentage of the dyestuff used.
  • Ex- COTTON VlSCOSE For comparison the table also includes the range incorample 150 3 WATER 3 WATER porated between lines A and B at these concentrations. 5 I 3 (3) 3 (24) (3) 4 (24)
  • Table III provides the figures obtained 2 4 (4) 34(4) 3-4(4-5) from a number of industrially-available reactive and di- 2 2 E2: 2 2 E11 rect dyes indentified by the Colour Index number 5 3 4 3-4 4 4 4-5 3 4 whlch do not conform to the test.
  • a process for coloring cellulose textile materials consisting essentially of impregnating the material with a water-soluble dye containing a cellulose-reactive group, fixing the dye on the material by treatment with an alkali applied in the dyebath or a separate bath in an amount conventionally used for that alkali for fixation of cellulose-reactive dyes, said dyestuff used exhibiting the following percentage exhaustions at different saline concentrations when dyed on to cotton or viscose rayon for 60 minutes at a strength of 0.5-1.0%, based on the weight of material being dyed, a liquor-to-goods ratio of 20:1 and a temperature of 80 C:
  • a process as claimed in claim 1 wherein the cold water to wash out loose dyestuff and dyebath addicellulose-reactive group present in the dyestuff is a tives. s-triazine group containing a single chlorine atom.

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US00225435A 1971-02-25 1972-02-11 Coloring cellulose textile material with a cellulose{14 reactive dye Expired - Lifetime US3816069A (en)

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US (1) US3816069A (enrdf_load_stackoverflow)
AR (1) AR195545A1 (enrdf_load_stackoverflow)
AU (1) AU3910272A (enrdf_load_stackoverflow)
BE (1) BE779635A (enrdf_load_stackoverflow)
BR (1) BR7201052D0 (enrdf_load_stackoverflow)
DD (1) DD96086A5 (enrdf_load_stackoverflow)
DE (1) DE2209107A1 (enrdf_load_stackoverflow)
FR (1) FR2126401B1 (enrdf_load_stackoverflow)
IT (1) IT951892B (enrdf_load_stackoverflow)
NL (1) NL7202360A (enrdf_load_stackoverflow)
ZA (1) ZA72926B (enrdf_load_stackoverflow)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3951588A (en) * 1973-09-20 1976-04-20 Ciba-Geigy Corporation Process for dyeing and printing or optical brightening of cellulose materials
US5234464A (en) * 1989-09-12 1993-08-10 Johannes Zimmer Method of dyeing textile webs with reactive dyestuffs: successive applications of reactive dye and alkali solutions
WO2006092815A1 (en) * 2005-03-04 2006-09-08 Lanificio Europa S.N.C. Di Piero E Luigi Guarducc I E Donatello Lombardi Method for permanently dyeing cellulose-based textiles, textiles and clothes obtained thereby
US20110045728A1 (en) * 2008-01-16 2011-02-24 Lenzing Ag Fiber Blends, Yarns And Fabrics Made Thereof
WO2015130437A1 (en) * 2014-02-05 2015-09-03 Rambler's Way Farm, Inc. Compositions and methods for dying natural fibers with natural dyes to ensure color (hue and shade)-match consistency

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3697500A (en) * 1967-08-21 1972-10-10 Ciba Geigy Ag Water-soluble disazo pyrazole dyestuffs containing fiber-reactive substituents

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE556776A (enrdf_load_stackoverflow) *

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3697500A (en) * 1967-08-21 1972-10-10 Ciba Geigy Ag Water-soluble disazo pyrazole dyestuffs containing fiber-reactive substituents

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Colour Index, Vol. 3, 3rd Ed., 1971, pp. 3,463, 3,533, 3,534. *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3951588A (en) * 1973-09-20 1976-04-20 Ciba-Geigy Corporation Process for dyeing and printing or optical brightening of cellulose materials
US5234464A (en) * 1989-09-12 1993-08-10 Johannes Zimmer Method of dyeing textile webs with reactive dyestuffs: successive applications of reactive dye and alkali solutions
WO2006092815A1 (en) * 2005-03-04 2006-09-08 Lanificio Europa S.N.C. Di Piero E Luigi Guarducc I E Donatello Lombardi Method for permanently dyeing cellulose-based textiles, textiles and clothes obtained thereby
US20110045728A1 (en) * 2008-01-16 2011-02-24 Lenzing Ag Fiber Blends, Yarns And Fabrics Made Thereof
WO2015130437A1 (en) * 2014-02-05 2015-09-03 Rambler's Way Farm, Inc. Compositions and methods for dying natural fibers with natural dyes to ensure color (hue and shade)-match consistency

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DE2209107A1 (de) 1972-10-05
FR2126401B1 (enrdf_load_stackoverflow) 1975-10-24
FR2126401A1 (enrdf_load_stackoverflow) 1972-10-06
BE779635A (fr) 1972-08-21
IT951892B (it) 1973-07-10
AU3910272A (en) 1973-08-23
AR195545A1 (es) 1973-10-23
BR7201052D0 (pt) 1973-08-23
ZA72926B (en) 1972-10-25
DD96086A5 (enrdf_load_stackoverflow) 1973-03-05
NL7202360A (enrdf_load_stackoverflow) 1972-08-29

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