EP0713940B1 - Procédé pour teindre des matériaux fibreux contenant de la laine - Google Patents

Procédé pour teindre des matériaux fibreux contenant de la laine Download PDF

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Publication number
EP0713940B1
EP0713940B1 EP95810682A EP95810682A EP0713940B1 EP 0713940 B1 EP0713940 B1 EP 0713940B1 EP 95810682 A EP95810682 A EP 95810682A EP 95810682 A EP95810682 A EP 95810682A EP 0713940 B1 EP0713940 B1 EP 0713940B1
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Prior art keywords
formula
radical
hydrogen
wool
chy
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German (de)
English (en)
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EP0713940A2 (fr
EP0713940A3 (fr
Inventor
Philippe Ouziel
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BASF Schweiz AG
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Ciba Spezialitaetenchemie Holding AG
Ciba SC Holding AG
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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
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/14—Wool
    • 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
    • D06P1/64—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 without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
    • D06P1/6495—Compounds containing carbonamide -RCON= (R=H or hydrocarbons)
    • 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
    • D06P1/60—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 polyethers
    • D06P1/613—Polyethers without nitrogen
    • D06P1/6136—Condensation products of esters, acids, oils, oxyacids with oxiranes
    • 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
    • D06P1/64—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 without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
    • D06P1/6495—Compounds containing carbonamide -RCON= (R=H or hydrocarbons)
    • D06P1/6497—Amides of di- or polyamines; Acylated polyamines
    • 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
    • D06P1/64—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 without sulfate or sulfonate groups
    • D06P1/651—Compounds without nitrogen
    • D06P1/65106—Oxygen-containing compounds
    • D06P1/65125—Compounds containing ester 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
    • D06P1/64—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 without sulfate or sulfonate groups
    • D06P1/651—Compounds without nitrogen
    • D06P1/65106—Oxygen-containing compounds
    • D06P1/65131—Compounds containing ether or acetal 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
    • D06P1/653—Nitrogen-free carboxylic acids or their salts
    • 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
    • D06P3/16—Wool using acid 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
    • 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
    • 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 new method for high temperature dyeing of Wool or wool-containing fiber materials.
  • the present invention thus relates to a process for dyeing wool-containing fiber materials with anionic dyes, which is characterized in that these materials in the presence of a wool protection agent containing at least one compound of the formula colors, in which R and R 'independently of one another each represent hydrogen, C 1 -C 6 alkyl or a cation, R 1 , R 2 , R 1 'and R 2 ' are each independently hydrogen, C 1 -C 6 alkyl or halogen B is a radical of the formula - X - Z 1 - - X - Z 2 - X - or - NR 3 - (alk) 0-1 - Z 1 - (alk) - NR 3 '- means X is a functional group -O- or -NR 3 -, where in the rest of the formula (2b) both radicals X stand for a group -O- or both radicals X stand for a group -NR 3 -, R 3 and R 3 '
  • C 1 -C 6 -alkyl generally means, for example, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or tert-butyl or straight-chain or branched pentyl or hexyl.
  • the cation includes, for example, alkali metal or alkaline earth metal cations such as sodium, potassium, lithium. Understand calcium or magnesium cation, the ammonium cation or organic ammonium cations such as the mono-, di- or triethanolammonium cation.
  • Halogen generally means, for example, fluorine, bromine or, in particular, chlorine.
  • C 1 -C 4 alkylene generally means, for example, methylene, 1,1- or 1,2-ethylene, 1,2- or 1,3-propylene or 1,2-, 1,3-, 1,4- or 2 , 3-butylene.
  • R or R 'in the meaning of an alkyl radical are preferably a C 1 -C 4 alkyl radical and particularly preferably methyl or ethyl.
  • R or R ' is a cation, it is preferably a Alkali metal cation, e.g. around the sodium, potassium or lithium cation, Ammonium cation or around the cation of an organic amine, e.g. around the mono-, di- or triethanolammonium cation.
  • R or R ' are particularly preferably each as a cation independently for the sodium, potassium or triethanolammonium cation.
  • R and R 'independently of one another each preferably represent hydrogen or a cation and particularly preferred for hydrogen or the sodium or potassium cation.
  • radicals R and R ' are preferably the same.
  • the radicals R 1 , R 2 , R 1 'and R 2 ' independently of one another are preferably each hydrogen, C 1 -C 4 -alkyl or chlorine.
  • the radicals R 1 , R 2 , R 1 'and R 2 ' are preferably the same. In a particularly preferred embodiment of the present invention, R 1 , R 2 , R 1 'and R 2 ' each represent hydrogen.
  • R 3 and R 3 'independently of one another are preferably each hydrogen or C 1 -C 4 -alkyl and particularly preferably hydrogen, methyl or ethyl.
  • the radicals R 3 and R 3 ' are preferably the same. In a particularly preferred embodiment of the present invention, R 3 and R 3 'each represent hydrogen.
  • X preferably represents the functional group -O-.
  • p, q and r independently of one another each preferably represent an integer from 0 to 8, where the sum of (p + q + r) is 2 to 8.
  • Z 1 radicals correspond to the formula - (CH 2 -CH 2 -O) p - (CHY 1 -CHY 2 -O) q - wherein Y 1 and Y 2 have the meaning given above and p and q are each independently an integer from 0 to 8, the sum of (p + q) being 2 to 8.
  • Z 1 particularly preferably represents a radical of the formula - (CH 2 -CH 2 -O) p - wherein p is an integer from 2 to 8 and especially 2 to 5.
  • the preferences previously given for R apply independently for R "and the preferences given previously for R 1 " and R 2 "each independently apply for R 1 and R 2.
  • the radical R" preferably has that the same meaning as R and R ', and the radicals R 1 "and R 2 " preferably have the same meaning as R 1 , R 1 ', R 2 and R 2 '.
  • Z 2 stands for the remainder of a tri-, tetra- or polyamine or tri-, tetra- or polyol, then this in each case preferably has C 12 carbon atoms and particularly preferably 3 to 8 carbon atoms.
  • Suitable tri, tetra or polyol residues Z 2 are the residue of glycerol, diglycerol, triglycerol, 1,1,1-tris (hydroxymethyl) propane, erythritol, pentaerythritol, arabitol, sorbitol or mannitol, in which free or partially hydroxyl groups in the form of an ester group of the formula (4b) given above.
  • a group of particularly suitable radicals of the formula (2b) given above is characterized in that X denotes a group -O- and Z 2 for the rest of a tri, tetra, penta- or hexaol having 3 to 6 carbon atoms and stands in particular for the remainder of a tri- or tetraol having 3 or 4 carbon atoms, the free hydroxyl groups of which are partly or completely in the form of an ester group of the formula (4b) given above.
  • Glycerol residues of the formula are particularly preferred as the residue of the formula (2b) wherein R "is hydrogen or a cation. If B in formula (1) represents a radical of the formula (2b ') given above, R, R' and R" preferably have the same meaning.
  • alkylene radical (alk) carries substituents, this can be, for example, a hydroxy, C 1 -C 4 alkoxy or sulfate radical.
  • the group (alk) preferably denotes an unsubstituted or substituted by hydroxy, C 1 -C 4 alkoxy or -OSO 3 H C 2 -C 4 alkylene radical and particularly preferably the 1,2-ethylene, 1,2- or 1 , 3-propylene or 2-hydroxy-1,3-propylene radical.
  • B represents a radical of the formula (2c) given above, this preferably corresponds to the formula -NR 3 - (alk) 0-1 - (CH 2 -CH 2 -O) p - (CHY 1 -CHY 2 -O) q - (alk) - NR 3 ' in which R 3 and R 3 'are identical and each represent hydrogen, methyl or ethyl, (alk) represents an unsubstituted or substituted by hydroxy, C 1 -C 4 alkoxy or -OSO 3 H, C 2 -C 4 alkylene radical, Y 1 and Y 2 have the meaning given above and p and q are each independently an integer from 0 to 8, the sum of (p + q) being 2 to 8.
  • B as the radical of the formula (2c) is particularly preferably a radical of the formula NH - (alk) 0-1 - (CH 2 -CH 2 -O) p - (alk) -NH - wherein (alk) is 1,2-ethylene, 1,2- or 1,3-propylene or 2-hydroxy-1,3-propylene and p is an integer from 2 to 8 and especially 2 to 5.
  • a preferred embodiment of the present invention relates to the method using a compound of the above formula (1), wherein R and R 'are the same and each represent hydrogen or a cation, R 1 , R 2 , R 1 'and R 2 ' are the same and are each hydrogen, C 1 -C 4 alkyl or chlorine, B is a radical of the formula -O- (CH 2 -CH 2 -O) p - (CHY 1 -CHY 2 -O) q - (CHY 3 -CHY 4 -O) r or -OZ 2 -O- means of Y 1 and Y 2 one is methyl and the other is hydrogen, of Y 3 and Y 4 one is ethyl and the other is hydrogen, p, q and r are each independently an integer from 0 to 8, the sum of (p + q + r) being 2 to 8, Z 2 stands for the remainder of a tri, tetra or polyol having 3 to 12 carbon atoms, the free
  • a particularly preferred embodiment of the present invention relates to the method using a compound of the formula wherein B represents a radical of the formula -O- (CH 2 -CH 2 -O) p - is R is hydrogen or the sodium or potassium cation and p is an integer 2 to 5.
  • the compounds of the formula (1) used according to the invention can be prepared in a manner known per se, for example by using a compound of the formula H-B'-H wherein B 'is a radical of the formula - X - Z 1 - - X - Z 2 - X - or - NR 3 - (alk) 0-1 - Z 1 - (alk) - NR 3 '- means X, Z 1 , R 3 , R 3 'and (alk) each have the meaning given above and Z 2 , when X is -NR 3 -, represents the rest of a tri-, tetra- or polyamine, or if X -O- is the residue of a tri-, tetra- or polyol which has 12 12 C atoms, in any order with the acid hydrides or mono-acid chlorides of carboxylic acids of the formulas and wherein R, R ', R ", R 1 , R 1 ', R 1 ",
  • the preferred compounds of formula (1) wherein R, R 'and R “, R 1 , R 1 ' and R 1 " and R 2 , R 2 'and R 2 "are each identical, can advantageously be prepared by using one Reacting compound of formula (5) with an acid anhydride or mono acid chloride from a carboxylic acid of formula (6a) given above in a molar excess.
  • R, R ', R "are each hydrogen or a cation and R 1 , R 1 ', R 1 ", R 2 , R 2 'and R 2 "are each hydrogen can advantageously be prepared by reacting a compound of formula (5) with maleic anhydride in a molar excess.
  • the reaction of the compound of formula (5) with the compounds of formula (6a) (6b) and (6c) advantageously take place at elevated temperature, e.g. at a temperature of 15 up to 150 ° C and preferably at 80 to 120 ° C instead.
  • the response time can be within further limits fluctuate, with a reaction time of approx. 1 to 10 hours and has proven to be practical for 1 to 5 hours.
  • the products of formula (1) obtained in the reaction can either be directly or but e.g. after previous dilution with one or more suitable solvents can be used as wool protection.
  • Solvents suitable for dilution are e.g. Water or alkylene glycols liquid at room temperature or Alkylene glycol ethers such as Polyethylene glycol 200, propylene glycol, diethylene glycol, Dipropylene glycol, triethylene glycol, tripropylene glycol or their monomethyl, Monoethyl, monobutyl, dimethyl, diethyl or dibutyl ether, e.g.
  • alkylene glycols is preferred as a diluent for the wool protection agents according to the invention.
  • the compounds of the formula (5), (6a), (6b) and (6c) are known per se or can be obtained by methods known per se.
  • the wool protection agents used according to the invention can contain one or more of the compounds of the formula (1).
  • An embodiment of the present invention is characterized in that a wool protection agent containing at least one compound of the formulas (1) and wherein R and Z 1 have the meanings given above, used. It is also possible to use wool protection agents which contain a compound of the formula (1) and a further compound with a wool-protecting action, for example 3-chloro-1,2-propanediol.
  • the compounds of the formula (1 ') can be prepared in an analogous manner, for example by adding the acid halide or acid anhydride of a compound of the formula (6a) given above, in which R 1 and R 2 are each hydrogen, with approximately equimolar amounts of a compound of the aforementioned formula (5), in which B 'is a radical of the formula (2a) in which X is -O-.
  • the wool-containing fiber material is first treated with the wool preservative pretreated in an aqueous bath and then by adding the dye colors to this bath. You can also proceed in such a way that you can dye the material at the same time treated with the wool preservative and the dye in an aqueous bath.
  • the wool protection agent in an amount of e.g. 0.1 to 20% by weight, preferably 0.1 to 10% by weight, particularly preferably 1 to 10% by weight and particularly preferably 1 to 6% by weight, based in each case on the weight of the material to be dyed, use.
  • the wool-containing fiber material can be wool alone or mixtures from e.g. Trade wool / polyamide or wool / polyester. Thereby mixtures are made Wool and synthetic polyamide preferably with anionic dyes and Mixtures of wool and polyester fibers preferably with dispersion and anionic Dyes colored. Suitable anionic dyes and disperse dyes are Known specialist.
  • the fiber material can be in various stages of processing, e.g. in Form of yarn, flake, sliver, knitwear, such as knitwear or knitted fabric, as Nonwoven fabric or preferably as a fabric.
  • the mixed fiber materials are preferably fiber mixtures Wool and polyester, which are usually in a proportion of 20 to 50 Parts by weight of wool are present to 80-50 parts by weight of polyester.
  • the one for the procedure preferred fiber blends contain 45 parts of wool and 55 parts of polyester fibers.
  • the liquor ratio can be within a wide range in the process according to the invention Range can be selected; it is e.g. 1: 1 to 1: 100 and preferably 1:10 to 1:50.
  • the dyebath can also be customary Additives included.
  • Additives included.
  • Mineral acids, organic acids and / or their salts which serve to adjust the pH of the dyebath, continue Electrolytes, leveling, wetting and defoaming agents and, if it is dyeing deals with wool / polyester mixtures, carriers and / or dispersants.
  • the dye bath has a pH of e.g. 4 to 6.5 and preferably 5.2 to 5.8 on.
  • the process according to the invention is generally carried out at a temperature of e.g. 60 to 130 ° C carried out.
  • the dyeing is expediently carried out the pull-out process, e.g. at a temperature in the range of 60 to 106 ° C, preferably 95 to 98 ° C.
  • the dyeing time can vary depending on the requirements, however, it is preferably 60-120 minutes.
  • the dyeing of the polyester / wool mixed fiber materials is advantageously carried out in a single bath from aqueous liquor after the exhaust process. It is preferably dyed according to the so-called high-temperature processes in closed, pressure-resistant equipment at temperatures above 100 ° C, expediently between 110 and 125 ° C and preferably at 118-120 ° C and optionally under pressure.
  • the mixed fiber materials can also be added using the usual carrier dyeing process Temperatures below 106 ° C, e.g. in the temperature range from 75 to 98 ° C in the presence one or more carriers are colored.
  • the dyeing of the polyester / wool mixed fiber materials can be carried out in such a way that the first thing to be dyed is the wool preservative and, if necessary, the carrier treated and then colored. You can also proceed in such a way that you dye the material at the same time with the wool protection agent, the dyes and, if necessary, auxiliaries treated.
  • the textile mixed fiber material is preferably added to a fleet, which contains the wool protection agent and possibly other conventional auxiliaries and a Has temperature of 40-50 ° C, and treated the material for 5 to 15 minutes Temperature. Then you raise the temperature to about 60 to 70 ° C, give the dye , heats up slowly to the dyeing temperature and then dyes about 20 to 60, preferably 30 up to 45 minutes at this temperature. At the end the fleet is heated to around 60 ° C cooled and the colored material worked up as usual.
  • a setting is an unwanted one during the dyeing process fixation of the wool fibers, which is caused by rearrangement of the wool contained disulfide bridges is caused.
  • Such undesirable fixations can e.g. in a deformation (flattening) of the wool yarns on bobbins, one Compacting the wool fibers as well as expressing a loss in the volume of the wool.
  • the antisetting effect of a wool protection agent can e.g. based on A.M. Wemys and M.A. White, Proc. Ind. Japan-Australia, Joint Symp. On objective measurement, Kyoto (1985), page 165, can be determined by making rondelles from wool test fabric punched out, folded in the middle and sewn together at the edge. The candidates are then in pressed state dyed in the presence of the wool protection agent, then the Fabric pattern opened and one thread pulled out. After a recovery period the angle of the threads is measured in warm water. The more that happened before compressed yarn has opened and the more the measured angle Approaching 180 °, the better the anti-setting effect of the wool protection agent. On measured angle of approx. 120 to 180 ° and in particular 140 to 180 ° shows a good one Anti-setting effect.
  • Parts mean parts by weight, Percentages by weight.
  • Example 2 18.4 parts of glycerol, 55.9 parts of maleic anhydride and 0.3 part of tributylamine are placed in a sulfonation flask. The mixture is carefully warmed to about 100 ° C. and then left to stir at this temperature for about 5 hours. The titration of the carboxyl groups indicates the end of the reaction. It is cooled to about 50 ° C., diluted with 40 parts of water and neutralized to pH 6 by adding about 303 parts of 2N sodium hydroxide solution. After filtering off undissolved particles, the compound of the formula is obtained as a 20% solution.
  • Example 5 20.1 parts of 1,1,1-trihydroxymethylpropane, 41.9 parts of maleic anhydride and 0.3 part of tributylamine are placed in a sulfonation flask. The mixture is carefully warmed to about 100 ° C. and then left to stir at this temperature for about 5 hours. The titration of the carboxyl groups indicates the end of the reaction. 58 parts of the product of the formula are obtained as a viscous oil.
  • Example 6a If the procedure is as described in Example 6 and, instead of the aqueous preparation according to Example 1, 1.7 parts of a mixture consisting of 93 parts of the product according to Example 1 and 7 parts of 3-chloro-1,2-propanediol are obtained, also a dye with good properties and without negatively influencing the wool quality.
  • Example 6b If the procedure described in Example 6 is followed and 2 parts of a mixture consisting of 50 parts of the product according to Example 1 and 50 parts of the product according to Example 5a are used instead of the aqueous preparation according to Example 1, a coloration with good properties is also obtained and without affecting the wool quality.
  • Example 7 100 parts of a wool fabric with a m2 weight of 180 g are in 1000 parts of an aqueous liquor containing 4 parts of ammonium sulfate, 2.0 parts of the product according to Example 1 and 0.5 parts of a naphthalenesulfonic acid condensate product for 10 minutes at 50 ° C treated; the pH of the liquor is previously adjusted to about 6 with acetic acid. Then 3 parts of the dye of the formula added and a further 5 min. treated. The dyeing liquor is then removed within approx. 45 min. heated to approx. 98 ° C and the tissue for 60 min. colored at this temperature. Then allow to cool to approx. 60 ° C, rinse as usual and dry the dyed fabric. You get a rub-fast, level blue color without negatively influencing the wool quality.
  • Example 7a If the procedure is as described in Example 7 and, instead of the aqueous preparation according to Example 1, 1.7 parts of a mixture consisting of 93 parts of the product according to Example 1 and 7 parts of 3-chloro-1,2-propanediol are obtained, also a dye with good properties and without negatively influencing the wool quality.
  • Example 7b If the procedure described in Example 7 is followed and 2 parts of a mixture consisting of 50 parts of the product according to Example 1 and 50 parts of the product according to Example 5a are used instead of the aqueous preparation according to Example 1, a coloration with good properties is also obtained and without affecting the wool quality.

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Claims (13)

  1. Procédé pour la teinture de matières fibreuses contenant de la laine par des colorants anioniques, caractérisé en ce qu'on teint ces matières en présence d'un agent de protection de la laine contenant au moins un composé de formule
    Figure 00290001
    où
    R et R' représentent chacun, indépendamment l'un de l'autre, un atome d'hydrogène, un groupe alkyle en C1-C6 ou un cation,
    R1, R2, R1' et R2' représentent chacun, indépendamment l'un de l'autre, un atome d'hydrogène, un groupe alkyle en C1-C6 ou un atome d'halogène.
    B représente un reste de formule -X-Z1- -X-Z2-X- ou -NR3-(alk)0-1-Z1-(alk)-NR3'- X représente un groupe fonctionnel -O- ou -NR3-, où dans le reste de formule (2b), les deux restes X représentent un groupe -O- ou les deux restes X représentent un groupe -NR3-,
    R3 et R3' représentent chacun, indépendamment l'un de l'autre, un atome d'hydrogène ou un groupe alkyle en C1-C6,
    Z1 représente un reste de formule -(CH2-CH2-O)p-(CHY1-CHY2-O)q-(CHY3-CHY4-O)r- un des restes Y1 et Y2, représente un groupe méthyle et l'autre reste représente un atome d'hydrogène,
    un des restes Y3 et Y4, un reste représente un groupe éthyle et l'autre reste représente un atome d'hydrogène,
    p, q et r sont, indépendamment les uns des autres, un entier de 0 à 20, où la somme de (p+q+r) va de 2 à 20,
    Z2 représente, lorsque X représente un groupe -NR3-, le reste d'une tri-, tétra- ou polyamine, dont les groupes amino libres se présentent partiellement ou complètement sous forme d'un groupe acylamino de formule -NR3-CO-CR1"=CR2"-CO-O-R" ou, lorsque X représente -O-, un reste d'un tri-, tétra- ou polyol qui présente ≤12 atomes de carbone, dont les groupes hydroxy libres se présentent partiellement ou complètement sous forme d'un groupe ester de formule - O - CO - CR1" = CR2" - CO - O - R" R" possède, indépendamment, la signification de R, et R1" et R2" possèdent chacun, indépendamment, la signification de R1 et de R2, et
    (alk) représente un reste alkylène en C1-C4 éventuellement substitué davantage.
  2. Procédé selon la revendication 1, caractérisé en ce que R, R' et R" sont identiques et chacun représente un atome d'hydrogène ou un cation.
  3. Procédé selon l'une des revendications 1 ou 2, caractérisé en ce que R1, R1', R1", R2, R2', R2", R3, R3' et R3" sont identiques et chacun représente un atome d'hydrogène.
  4. Procédé selon l'une des revendications 1 à 3, caractérisé en ce que B représente un reste de formules (2a) ou (2b) indiquées à la revendication 1 et X représente un groupe fonctionnel -O-.
  5. Procédé selon l'une des revendications 1 à 4, caractérisé en ce que Z1 représente un reste de formule -(CH2-CH2-O)p-(CHY1-CHY2-O)q- où Y1 et Y2 possèdent la signification indiquée à la revendication 1 et p et q sont chacun, indépendamment l'un de l'autre, un entier de 0 à 8, où la somme de (p+q) va de 2 à 8.
  6. Procédé selon l'une des revendications 1 à 5, caractérisé en ce que Z1 représente un reste de formule -(CH2-CH2-O)p- où p est un entier de 2 à 8 et notamment de 2 à 5.
  7. Procédé selon l'une des revendications 1 à 6, caractérisé en ce que X représente un groupe -O- et Z2 représente le reste d'un tri-, tétra-, penta- ou hexaol présentant 3 à 6 atomes de carbone et en particulier le reste d'un tri- ou tétraol présentant 3 ou 4 atomes de carbone, dont les groupes hydroxy libres se présentent chaque fois partiellement ou complètement sous forme d'un groupe ester de formule (4b) indiquée à la revendication 1.
  8. Procédé selon l'une des revendications 1 à 7, caractérisé en ce que B représente un reste de formule
    Figure 00310001
    où R" représente un atome d'hydrogène ou un cation.
  9. Procédé pour la teinture de matières fibreuses contenant de la laine par des colorants anioniques selon la revendication 1, caractérisé en ce qu'on teint ces matières en présence d'un agent de protection de la laine contenant au moins un composé de formule (1) indiquée à la revendication 1, où R et R' sont identiques et chacun représente un atome d'hydrogène ou un cation,
    R1, R2, R1' et R2' sont identiques et chacun représente un atome d'hydrogène, des groupes alkyle en C1-C4 ou chloro,
    B représente un reste de formule -O-(CH2-CH2-O)p-(CHY1-CHY2-O)q-(CHY3-CHY4-O)r ou -O-Z2-O- un des restes Y1 et Y2 représente un groupe méthyle et l'autre reste un atome d'hydrogène,
    un des restes Y3 et Y4 représente un groupe éthyle et l'autre reste un atome d'hydrogène,
    p, q et r représentent chacun, indépendamment les uns des autres, un entier de 0 à 8, où la somme de (p+q+r) va de 2 à 8,
    Z2 représente le reste d'un tri-, tétra- ou polyol présentant 3 à 12 atomes de carbone, dont les groupes hydroxy libres se présentent partiellement ou complètement sous forme d'un groupe ester de formule -O-CO-CR1"=CR2"-CO-O-R" et
    R" possède la signification de R et R1" et R2" possèdent chacun la signification de R1 et R2.
  10. Procédé pour la teinture de matières fibreuses contenant de la laine par des colorants anioniques selon la revendication 1, caractérisé en ce qu'on teint ces matières en présence d'un agent de protection de la laine contenant au moins un composé de formule
    Figure 00320001
    où R représente un atome d'hydrogène ou un cation,
    B représente un reste de formule -O-(CH2-CH2-O)p-(CHY1-CHY2-O)q- ou -O-Z2-O- un des restes Y1 et Y2 représente un groupe méthyle et l'autre reste un atome d'hydrogène, p et q sont chacun indépendamment l'un de l'autre un entier de 0 à 8, où la somme de (p+q) va de 2 à 8, et Z2 représente un reste d'un tri-, tétra- ou polyol présentant 3 à 6 atomes de carbone, dont les groupes hydroxy libres se présentent partiellement ou complètement sous forme d'un groupe ester de formule -O-CO-CH=CH-CO-O-R et
    dans laquelle R possède la signification donnée ci-dessus.
  11. Procédé pour la teinture de matières fibreuses contenant de la laine par des colorants anioniques selon la revendication 1, caractérisé en ce qu'on teint ces matières en présence d'un agent de protection de la laine contenant au moins un composé de formule
    Figure 00330001
    dans laquelle B représente un reste de formule -O-(CH2-CH2-O)p - R représente un atome d'hydrogène ou le cation sodium ou potassium et p est un entier qui va de 2 à 5.
  12. Procédé selon l'une des revendications 1 à 11, caractérisé en ce qu'on teint la matière fibreuse contenant la laine en présence de 0,1 à 10 % en masse, par rapport au produit à teindre, d'un ou plusieurs composés de formule (1).
  13. Procédé selon l'une des revendications 1 à 12 pour la teinture de matières fibreuses mixtes laine/polyester selon le procédé d'étirement.
EP95810682A 1994-11-08 1995-10-31 Procédé pour teindre des matériaux fibreux contenant de la laine Expired - Lifetime EP0713940B1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
CH3338/94 1994-11-08
CH333894 1994-11-08
CH333894 1994-11-08
CH147495 1995-05-18
CH147495 1995-05-18
CH1474/95 1995-05-18

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EP0713940A2 EP0713940A2 (fr) 1996-05-29
EP0713940A3 EP0713940A3 (fr) 1998-05-06
EP0713940B1 true EP0713940B1 (fr) 2002-04-24

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CA (1) CA2162217A1 (fr)
DE (1) DE59510179D1 (fr)
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ITBO20050638A1 (it) * 2005-10-24 2007-04-25 Manrico S P A Procedimento per la produzione di filati e prodotti tessili in cachemire, filati e prodotti cosi' ottenuti
KR100988978B1 (ko) * 2008-06-23 2010-10-20 한국염색기술연구소 양모와 폴리유산섬유의 합연사의 염색방법

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US4778919A (en) * 1986-02-25 1988-10-18 Ciba-Geigy Corporation Maleic or phthalic acid half esters of alkoxylated fatty amines
NZ225841A (en) * 1987-08-19 1991-02-26 Commw Scient Ind Res Org Treatment of textile materials comprising keratinous fibres using maleic acid or fumaric acid derivatives
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CA2162217A1 (fr) 1996-05-09
US5611820A (en) 1997-03-18
KR100362618B1 (ko) 2003-03-15
EP0713940A2 (fr) 1996-05-29
JPH08209552A (ja) 1996-08-13
AU3770795A (en) 1996-05-16
AU695343B2 (en) 1998-08-13
NZ280403A (en) 1997-09-22
KR960018057A (ko) 1996-06-17
EP0713940A3 (fr) 1998-05-06
DE59510179D1 (de) 2002-05-29
ES2173161T3 (es) 2002-10-16

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