EP0474594A1 - Procédé de teinture de la laine et ses mélanges avec d'autres fibres avec des colorants réactifs - Google Patents

Procédé de teinture de la laine et ses mélanges avec d'autres fibres avec des colorants réactifs Download PDF

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Publication number
EP0474594A1
EP0474594A1 EP91810659A EP91810659A EP0474594A1 EP 0474594 A1 EP0474594 A1 EP 0474594A1 EP 91810659 A EP91810659 A EP 91810659A EP 91810659 A EP91810659 A EP 91810659A EP 0474594 A1 EP0474594 A1 EP 0474594A1
Authority
EP
European Patent Office
Prior art keywords
formula
hydrogen
so3m
radical
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP91810659A
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German (de)
English (en)
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EP0474594B1 (fr
Inventor
Gerhard Dr. Back
Klaus Dr. Hannemann
Josef Koller
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Schweiz AG
Original Assignee
Ciba Geigy AG
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Filing date
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Publication of EP0474594A1 publication Critical patent/EP0474594A1/fr
Application granted granted Critical
Publication of EP0474594B1 publication Critical patent/EP0474594B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • D06P3/82—Textiles which contain different kinds of fibres
    • D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
    • D06P3/8214—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing ester and amide groups
    • 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
    • D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/62—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
    • D06P1/628—Compounds containing nitrogen
    • 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
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/14—Wool
    • D06P3/148—Wool using reactive dyes
    • 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
    • D06P3/82—Textiles which contain different kinds of fibres
    • D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
    • D06P3/8209—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing amide groups
    • 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
    • Y10S8/917—Wool or silk

Definitions

  • the present invention relates to a method for fiber and flat level dyeing of wool and their mixtures with other fibers with reactive dyes, the material dyed by the new method and a means for carrying out the method.
  • the present invention thus relates to a process for fiber and surface level dyeing of wool and their mixtures with other fibers with reactive dyes, which is characterized in that an aqueous liquor is used for dyeing these materials, which contains at least one colorless, fiber-reactive compound of the formula (1)
  • a ( ⁇ B-A) n contains, in which n is 0 or 1, and when n is 1, A is a residue of the formula B is an alkylene or alkenylene group or the direct bond, or if n is zero, A is a compound of the formula or the formula means where in formulas (1) to (4)
  • R1 is a radical of the formula
  • Hal is halogen
  • R is hydrogen or halogen, n1 1 or 0,
  • R2 is hydrogen, SO3M or -NH2
  • R3 is hydrogen, SO3M or a radical of the formula -OX, wherein X is hydrogen or C1 to C4 alkyl
  • R4 is hydrogen, SO3M or a radical of the formula mean and
  • M is hydrogen, alkali metal or ammonium and the compound of formula (4) has at least one - SO3M - group and the coloring is completed regardless of the depth of color at a pH of 4.0 to 5.0.
  • the alkylene radical in formula (1) represents a divalent, saturated hydrocarbon radical which contains 2 or 3 carbon atoms, such as ethylene, trimethylene or propylene.
  • the alkenylene radical in formula (1) represents a divalent unsaturated hydrocarbon radical which contains 2 or 3 carbon atoms, such as ethenylene or propenylene.
  • Lithium, potassium or preferably sodium are suitable as alkali metals.
  • Preferred colorless, fiber-reactive compounds correspond to the formula wherein R5 is hydrogen or SO3M and R6 is a residue of the formula or the formula mean and M has the meaning given in formula (3).
  • colorless fiber-reactive compounds correspond to the formula wherein R3, R5, R6 and M have the meanings given above.
  • the present method is particularly suitable for producing light to medium shades.
  • the colorless, fiber-reactive compounds of formula (1) are known per se Methods prepared by reacting an aromatic amino compound of the formula Ar-NH2, where Ar is an optionally substituted phenyl or naphthalene radical, in an acylation reaction with an alkyl or alkenyl halide.
  • the amounts used in which the colorless, fiber-reactive compounds are added to the dyebath range from 0.3 to 3, preferably 1 to 2 percent by weight, based on the fiber material to be dyed.
  • wool or mixtures of wool with other fiber materials are suitable.
  • Wool is preferably used for the process according to the invention.
  • the fiber material can be presented in various forms. Examples include: flake, sliver, yarn, fabric, knitwear or carpets.
  • the wool can be finished normally or without felt.
  • the organic dyes known under this term - regardless of the type of their reactive group - are suitable as reactive dyes.
  • dyes This class of dyes is referred to in the Color Index 3rd edition 1971 as "reactive dyes". These are predominantly those dyes which contain at least one group which is reactive with polyhydroxyl fibers (cellulose fibers) or polyamide fibers, in particular wool, a precursor therefor or a substituent which is reactive with polyhydroxyl fibers or polyamide fibers.
  • Suitable bases for the reactive dyes are particularly those from the series of the mono-, dis- or polyazo dyes including the formazan dyes and the anthraquinone, xanthene, nitro, triphenylmethane, naphthoquinoneimine, dioxazine and phthalocyanine dyes, the azo and phthalocyanine dyes can be both metal-free and metal-containing.
  • Reactive groups and precursors which form such reactive groups include, for example, epoxy groups, the ethyleneimide group, the vinyl grouping in vinylsulfone or in acrylic acid residues and the ⁇ -sulfatoethylsulfone group, the ⁇ -chloroethylsulfone group or the ⁇ -dialkylaminoethylsulfone group.
  • the reactive substituents in reactive dyes are those that are easily removable and leave an electrophilic residue.
  • substituents are 1 or 2 halogen atoms in an aliphatic acyl radical, e.g. in the ⁇ position or ⁇ and ⁇ position of a propionyl radical or in the ⁇ and / or ⁇ position of an acrylic acid radical, or 1 to 3 halogen atoms on the following ring systems into consideration: pyridazine, pyrimidine, pyridazone, triazine, quinoxaline or phthalazine.
  • Dyes with two or more identical or different reactive groups can also be used.
  • Preferred reactive dyes contain chloroacrylic, dichloropropionyl, chloroacetyl, bromoacrylic or dibromopropionyl as reactive substituents.
  • the reactive dyes can be acidic, salt-forming substituents such as e.g. Contain carboxylic acid groups, sulfuric acid and phosphonic acid ester groups, phosphonic acid groups or preferably sulfonic acid groups.
  • Reactive dyes with at least one sulfonic acid group are preferred, in particular reactive dyes with an azo or anthraquinone base body which preferably has two to three sulfonic acid groups.
  • the coloring takes place after the pull-out procedure.
  • the amount of dyes added to the dye liquor depends on the desired color strength. In general, amounts of 0.01 to 10 percent by weight, preferably 0.01 to 2 percent by weight, based on the fiber material used, have proven successful.
  • the liquor ratio can be chosen within a wide range e.g. 1: 3 to 1: 100, preferably 1: 8 to 1:30.
  • the dyebaths can contain mineral acids such as sulfuric acid or phosphoric acid, organic acids, expediently aliphatic carboxylic acids such as formic acid, acetic acid, Contain oxalic acid or citric acid and / or salts such as ammonium acetate, ammonium sulfate or sodium acetate.
  • the acids are used primarily to adjust the pH of the liquors used according to the invention, which is between 4 and 5.
  • the dyeing liquors also contain commercially available leveling agents which serve to increase fiber levelness.
  • Alkoxylated fatty amine derivatives are preferably used for the process according to the invention, with addition products of 5 to 12 moles of ethylene oxide and 1 mole of a fatty amine being of primary interest.
  • the dyeing liquors can also contain other auxiliaries customary in dyeing technology, e.g. Stabilizers, activators, dispersants, electrolytes, wetting agents, defoamers, antifoams, thickeners or wool protection agents.
  • the usual dyeing apparatus such as, for example, open baths, combed, strand yarn or packing apparatus, jigger, paddle apparatus, tree dyeing apparatus, circulation or jet dyeing apparatus or reel runners can be used.
  • the dyeing is advantageously carried out at a temperature in the range from 60 to 120 ° C., preferably 70 to 105 ° C.
  • the dyeing time is within the usual range and is usually 20 to 120 minutes.
  • the dyeing process can be followed by an alkaline after-treatment, e.g. with aqueous ammonia alkali metal hydroxides, alkali metal carbonates, bicarbonates or hexamethylenetetraamine.
  • the pH of the dye baths containing alkali is expediently 7.5 to 9, preferably 8 to 8.5.
  • the dyeing of the fiber material is expediently carried out by briefly treating the material to be dyed with an aqueous liquor which contains the acid, a leveling agent and the colorless, fiber-reactive compound and has a temperature of 30 to 60 ° C., and the reactive dye in the same bath adds. The temperature is then slowly increased in order to dye in a range from 80 to 100 ° C. and for 20 to 90, preferably 30 to 60 minutes. The material to be dyed is then treated for 10 to 20 minutes at 70 to 90 ° C. after addition of alkalis, preferably sodium hydrogen carbonate or sodium carbonate. Finally, the colored material is pulled out and rinsed, acidified and dried as usual.
  • alkalis preferably sodium hydrogen carbonate or sodium carbonate
  • the dyeing process according to the invention gives fiber and flat dyeings, especially in light to medium shades with good light and wet fastness properties.
  • the present invention furthermore relates to the dyeing aid which, in addition to the customary carriers, comprises at least one colorless, fiber-reactive compound of the formula (1)
  • a ( ⁇ B-A) n contains, in which n is 0 or 1, and when n is 1, A is a residue of the formula B is an alkylene or alkenylene group or the direct bond, or if n is zero, A is a compound of the formula or the formula means where in formulas (1) to (4)
  • R1 is a radical of the formula or the formula wherein Hal is halogen R is hydrogen or halogen, n1 1 or 0,
  • R2 is hydrogen, SO3M or -NH2
  • R3 is hydrogen, SO3M or a radical of the formula -OX, wherein X is hydrogen or C1 to C4 alkyl, R4 is hydrogen, SO3M or a radical of the formula mean and
  • M represents hydrogen, alkali metal or ammonium and the compound of formula (4) has at least one - SO3M - group.
  • Preferred dyeing aids contain at least one compound of the formula wherein R5 hydrogen or SO3M and R6 is a residue of the formula or the formula mean and M has the meaning given in formula (3). Further preferred dyeing aids contain at least one compound of the formula wherein R3, R5, R6, M and X have the meanings given in the formulas (4) and (6).
  • the auxiliaries according to the invention are also preferably used as wool protection agents in the dyeing of wool and their mixtures with other fibers, in particular fiber mixtures of wool and polyester in the high temperature range. They improve the mechanical properties of the fiber and reduce the yellowing of the wool.
  • the auxiliaries according to the invention thus represent a full substitute for conventional formaldehyde-containing wool protection agents.
  • the amounts used in this application are between 1 and 6%, based on the treated fiber material, the compounds being usable in combination with all acid dyes with and without reactive groups.
  • the auxiliaries according to the invention can also be used for the dirt-repellent finishing of wool fiber material.
  • auxiliaries according to the invention prevent the formation of wool degradation products with a reducing effect. They therefore enable the dyeing of textile combinations with synthetic fibers, such as wool / polyester or wool / polyacrylic, in which the synthetic fiber portion is dyed with reduction-sensitive dyes.
  • the compounds used for the process according to the invention are partly. known, for example from DE-A-2 328 834. Some of the colorless fiber-reactive compounds are also new compounds. These new compounds form a further subject of the present invention.
  • the new, colorless, fiber-reactive compounds correspond to the formula wherein R'1 is a radical of the formula or a residue of the formula means wherein Hal is halogen R ′ is hydrogen or halogen and M ′ is hydrogen or alkali metal and n'1 1 or 0 mean.
  • R'1 has the meaning given in formula (1 ')
  • R'2 is hydrogen
  • X ′ is hydrogen or C1 to C4 alkyl
  • p 1 or 0 and R'3 is hydrogen
  • SO3M 'or a radical of the formula means where M ′ has the meaning given in formula (2 ′)
  • R′3 is SO3M ′ and the NHR1 radical in formula (2 ′) is in the 2 position and p means 1, and when R'2 SO3M 'means R'3 is hydrogen and p 1.
  • the new, water-soluble, fiber-reactive compounds according to the invention are produced in a manner known per se.
  • the compounds of the formulas (1 ') and (2') are prepared, for example, by using a compound of the formula or the formula where M ′ is hydrogen or alkali, R'2 is hydrogen or a radical of the formula OX ', wherein X ′ is hydrogen or C1 to C4 alkyl, p 0 or 1 and R'3 is hydrogen, SO3M 'or a radical of the formula mean, where, when X ′ is hydrogen, R′3 is SO3M ′, the NH2 radical is in the 2-position and p is 1, and when R′2 is SO3M ′, R′3 is hydrogen and p 1, with a compound of the formula or the formula wherein Hal is chlorine or bromine and R ′ is hydrogen, chlorine or bromine and n'1 mean 0 or 1, implements.
  • the reaction time of this reaction lasts between 1 and 6, preferably 1 and 3 hours. During the reaction, a pH of 3 to 7, preferably 5 to 6, is maintained. The reaction temperature is between 0 and 20 ° C.
  • the known and new colorless, fiber-reactive compounds serve as precursors for reactive dyes.
  • the resulting compound is separated from the reaction solution by adding 75 parts of potassium chloride, isolated by filtration and, after washing the filter cake, dried in vacuo at 50 ° with 30% potassium chloride solution.
  • the yield is 55 parts of 2- (2 ', 3'-dibromopropionyl) amino-8-hydroxy-naphthalene-3,6-disulfonic acid of the formula as a potassium salt in the form of a light gray, slightly water-soluble powder.
  • an alkaline aftertreatment for example with ammonia, sodium carbonate or sodium hydrogen carbonate, can be connected to improve the fastness properties.
  • the fiber-reactive, colorless compounds of the formulas (109) to (120) are used in amounts of 0.5 to 2%, based on the fiber weight. Similar results are obtained.
  • 4 blind dye liquors are prepared, which have a pH of 4.5, which is adjusted with an acetic acid / acetate buffer.
  • 0.6 g of the colorless, fiber-reactive compound of the formula (110), 0.6 g of the colorless, fiber-reactive compound of the formula (112), 0.6 g of a wool preservative based on formaldehyde are added to the liquor 1 .
  • the fleet 4 contains no further additives.
  • 20 g of wool fabric is treated at 120 ° for 30 minutes.
  • the temperature of the individual dyeing liquors is increased from 40 ° to 120 ° within 40 minutes.
  • the dyeing is then carried out at 120 ° for 40 minutes. After cooling to 70 °, rinsing is carried out and the coloring is finished as usual.
  • the dyeing results are then compared.
  • the dyeings of liquors 2 and 3 are significantly more bluish, since the reduction-sensitive dye of the formula (122) bleaches less strongly in the presence of the colorless fiber-reactive compounds. The difference becomes even clearer if the wool is removed by treating it with boiling 5% sodium hydroxide for five minutes. The polyester portion is stained much weaker without the addition.
  • the temperature of the individual dyeing liquors is increased from 40 ° to 120 ° within 40 minutes.
  • the dyeing is then carried out at 120 ° for 40 minutes. After cooling to 70 °, rinsing is carried out and the coloring is finished as usual.
  • the polyester dyeings are then evaluated colorimetrically. The values are shown in the following table:

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP91810659A 1990-08-28 1991-08-20 Procédé de teinture de la laine et ses mélanges avec d'autres fibres avec des colorants réactifs Expired - Lifetime EP0474594B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH278790 1990-08-28
CH2787/90 1990-08-28

Publications (2)

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EP0474594A1 true EP0474594A1 (fr) 1992-03-11
EP0474594B1 EP0474594B1 (fr) 1997-03-12

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EP91810659A Expired - Lifetime EP0474594B1 (fr) 1990-08-28 1991-08-20 Procédé de teinture de la laine et ses mélanges avec d'autres fibres avec des colorants réactifs

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US (1) US5207799A (fr)
EP (1) EP0474594B1 (fr)
JP (1) JPH04245984A (fr)
DE (1) DE59108604D1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2824106A1 (fr) 2001-04-30 2002-10-31 Aerospatiale Matra Missiles Manche a air et engin volant, en particulier un missile, muni d'une telle manche a air

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111535056A (zh) * 2020-05-28 2020-08-14 张家港扬子染整有限公司 一种羊毛羊驼毛纱线染色工艺
JP2023139758A (ja) * 2022-03-22 2023-10-04 株式会社カネカ セルロース系繊維及び再生タンパク質繊維を含む混紡繊維が染色されてなる染色布帛、及びその製造方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2128834A1 (de) * 1970-06-11 1971-12-23 Ciba-Geigy Ag, Basel (Schweiz) Verfahren zur Erzeugung von Mehrfarbeneffekten auf natürlichem und synthetischem Polyamidfasermaterial
US4218217A (en) * 1974-04-01 1980-08-19 Sandoz, Inc. Method of producing multicolor dyeings

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2895785A (en) * 1959-07-21 Naoas
US3700402A (en) * 1970-06-29 1972-10-24 Hideyo Noda Resist printing under reactive dye with alkali hydroxy methane sulfonate or amino and amido methane sulfonate
DE3363011D1 (en) * 1982-03-12 1986-05-22 Ciba Geigy Ag Process for dyeing fibrous material from natural polyamides
DE3439532A1 (de) * 1984-10-29 1986-04-30 Hoechst Ag, 6230 Frankfurt Verfahren zum erzeugen von weiss- und buntreserven auf polyamidfasermaterialien

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2128834A1 (de) * 1970-06-11 1971-12-23 Ciba-Geigy Ag, Basel (Schweiz) Verfahren zur Erzeugung von Mehrfarbeneffekten auf natürlichem und synthetischem Polyamidfasermaterial
US4218217A (en) * 1974-04-01 1980-08-19 Sandoz, Inc. Method of producing multicolor dyeings

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2824106A1 (fr) 2001-04-30 2002-10-31 Aerospatiale Matra Missiles Manche a air et engin volant, en particulier un missile, muni d'une telle manche a air
US6575404B2 (en) 2001-04-30 2003-06-10 Medam F Air intake and flying device, particularly a missile, equipped with such an air intake

Also Published As

Publication number Publication date
JPH04245984A (ja) 1992-09-02
US5207799A (en) 1993-05-04
DE59108604D1 (de) 1997-04-17
EP0474594B1 (fr) 1997-03-12

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