EP0924334B1 - Procédé de teinture de matériaux textiles comprenant des fibres de polyester - Google Patents

Procédé de teinture de matériaux textiles comprenant des fibres de polyester Download PDF

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Publication number
EP0924334B1
EP0924334B1 EP98122283A EP98122283A EP0924334B1 EP 0924334 B1 EP0924334 B1 EP 0924334B1 EP 98122283 A EP98122283 A EP 98122283A EP 98122283 A EP98122283 A EP 98122283A EP 0924334 B1 EP0924334 B1 EP 0924334B1
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EP
European Patent Office
Prior art keywords
dyeing
glycine
process according
alkaline
dye bath
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.)
Expired - Lifetime
Application number
EP98122283A
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German (de)
English (en)
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EP0924334A3 (fr
EP0924334A2 (fr
Inventor
Mark Dohmen
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Dohmen M GmbH
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Dohmen M GmbH
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Publication date
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Publication of EP0924334A2 publication Critical patent/EP0924334A2/fr
Publication of EP0924334A3 publication Critical patent/EP0924334A3/fr
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Publication of EP0924334B1 publication Critical patent/EP0924334B1/fr
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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
    • 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
    • D06P1/673—Inorganic compounds
    • D06P1/67391—Salts or oxidising-compounds mixtures
    • 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
    • D06P1/647—Nitrogen-containing 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
    • 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
    • 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
    • D06P1/673—Inorganic compounds
    • D06P1/67333—Salts or hydroxides
    • D06P1/6735—Salts or hydroxides of alkaline or alkaline-earth metals with anions different from those provided for in D06P1/67341
    • 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
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • D06P3/54—Polyesters using dispersed dyestuffs
    • 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
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/922—Polyester fiber

Definitions

  • the invention relates to a process for dyeing textile material comprising polyester fibers, in which the textile material is treated in an alkaline dyebath containing a disperse dye at a temperature above 100 ° C.
  • polyester dyeing at temperatures above 100 ° C - ie under pressure By polyester dyeing at temperatures above 100 ° C - ie under pressure - shorter dyeing times can be achieved than under normal pressure. In addition, through-dyeing, balance of fusing and stretching differences, color yield and color fastness under high-temperature (HT) conditions are improved.
  • HT conditions the following problem arises under HT conditions in the dyeing baths commonly used in acid dyeing baths: during the dyeing process, low molecular weight oligomers are released from the interior of the fibers which are by-produced in the spinning of polyester filaments. These low molecular weight oligomers are deposited in the acid dyebath on cooling the dye liquor on the fiber surface and on the surfaces of the dyeing.
  • alkaline dyebaths Under alkaline conditions, the solubility of the oligomers is increased. Furthermore, partial saponification of the released oligomers takes place, as a result of which the undesired deposits are considerably reduced. Furthermore, in alkaline dyeing, reductive or alkaline aftertreatment can be dispensed with in many cases.
  • the dyeing process When using the known acidic dyebaths, the dyeing process is generally the only treatment step in an acidic medium. Accordingly, alkaline dyeing avoids a pH change and thus minimizes the risk of entrained alkali.
  • Another advantage is that one-bath dyeing processes of polyester-cellulose fiber blends with direct dyes are also possible in the alkaline, which provides additional choices for corresponding direct dyes.
  • an alkaline dyeing bath it is basically possible to combine the washing and desizing of polyester fabrics in a bath with the dyeing. Furthermore, recrystallization of fiber degradation products from splitting and peeling processes by the alkali is prevented.
  • the disperse dyes used in the acid dyebath are more alkaline.
  • Dyebath partially unstable.
  • the destruction of the dyes takes place by hydrolysis of ester compounds in the side chains of the dye molecules.
  • the degree of this hydrolysis is largely dependent on the pH of the dyebath during the entire dyeing process.
  • the pH is subject to fluctuations, which can lead to non-reproducible staining results.
  • Another problem is heavy metal ions and polyvalent metal ions in the dyebath, whose presence in varying concentrations can not be reliably ruled out industrially.
  • the influence of the heavy metal and metal ions (eg Cu 2+ , Fe 2+ ) on the dyeing result is generally considerably greater in the alkaline dyebath than in the acid dyebath.
  • the influence of hardness agents in the water of the dyebath on the dyeing result in alkaline is much greater than in the acidic.
  • other substances such as glucose as a degradation product of Schlichteresten, can adversely affect the dyeing result in the alkaline.
  • the stronger influence of the aforementioned substances in the alkaline is partly due to the fact that the reduction potential in the alkaline is always greater than in the acid, so that it can lead to irreversible reduction of the dyes.
  • the concentration of auxiliary substances dissolved in the dyebath is limited by the fact that if the concentration is too high, the generally sparingly soluble disperse dyestuffs can no longer be kept in solution despite the use of dispersants.
  • DE 39 38 631 A1 discloses a process for dyeing polyester-containing textile material in an alkaline dyebath, in which an amino acid or an amino acid derivative and an alkali metal salt of the amino acid or of the amino acid derivative are added to the dyebath.
  • an amino acid or an amino acid derivative and an alkali metal salt of the amino acid or of the amino acid derivative are added to the dyebath.
  • Example XIII a copper-containing metal salt solution is proposed, which i.a. from glycine, caustic soda and a high concentration of 100 g of sodium perborate to 400 g of water (corresponding to 250 g / l of sodium perborate).
  • the known dyeing method is not transferable to the dyeing of polyester-containing textile material by means of disperse dyes.
  • the invention is accordingly an object of the invention to improve a process for dyeing textile material of polyester and its fiber blends of the type mentioned in such a way that the above-mentioned problems are avoided.
  • the deposition of oligomers on Därbegut and Därbevorraumen should be avoided and at the same time an industrially reproducible, consistently high-quality dyeing result can be achieved.
  • the solution of this object is achieved according to one aspect of the invention, characterized in that the adjustment of the pH of the dyebath by initial addition of a buffer mixture of glycine and / or a glycine derivative and a liquor before the beginning of the dyeing process, and that the dyebath a Perboratsalz is added ,
  • the pH of the dyebath is adjusted by initially adding a buffer mixture of glycine and caustic soda before the start of the dyeing process and sodium perborate is added to the dyebath prior to the beginning of the dyeing process, so that the pH is increased by the action of the buffer mixture from the beginning is kept substantially constant until the end of the dyeing process.
  • a double buffer system is provided by which a sufficient pH consistency is ensured until the end of the dyeing process and simultaneously counteracts reductive processes, without the disperse dye through the buffer substances from the solution is displaced.
  • the invention is i.a. the finding that in known alkaline dyeing method, the pH is not kept sufficiently stable. Above all, due to the saponification of the oligomers, the initially set pH decreases as a result of consumption of alkali towards the end of the dyeing process, with the result that initially saponified and dissolved oligomers precipitate again. This effect is counteracted by a powerful buffer mixture. In addition, unwanted pH changes are prevented by acidic or alkaline Därbebad horrile by the buffer system, thus achieving a consistent dyeing result.
  • a glycine / caustic soda buffer (or glycine / glycine-alkali metal salt buffer) is used for buffering, which operates chemically as follows:
  • glycine and caustic soda co-act in the context of the invention as a buffer, by which a pH constancy is achieved until the end of dyeing, could be demonstrated by experimentally varying the ratio glycine / caustic soda.
  • the staining result became optimal just when the components mentioned were added to the dyebath in a predetermined by the appropriate buffer equation for the desired pH ratio. If the ratio is shifted in favor of the alkali, ie a pH greater than 9.5 is produced, then an instability of the dyes is observed, ie the color is not reproducible. If the ratio is shifted in favor of glycine, the buffer capacity is no longer sufficient and the final pH is well below 9.0, which leads to a redeposition of the oligomers, or their degradation products.
  • both glycine and a glycine derivative in which a hydrogen of the amino group is replaced by an organic group can be used.
  • Unsubstituted glycine proves to be particularly advantageous since the use of a glycine derivative makes it difficult to take up another proton for acid formation, which slows down the adjustment of the buffer equilibrium.
  • the hydrophobic radicals of a substituted amine group also show an increased dispersing effect by which the disperse dye is kept longer in the dyebath and thus the dyeing process is prolonged.
  • a perborate salt preferably sodium perborate
  • a perborate salt is additionally added in accordance with the invention in such a way that hydrogen peroxide is liberated at the dyeing temperature as oxidizing agent and a mixture of borax and caustic soda stabilizing the pH according to the following equation: 4NaBO 3 + 5H 2 O ⁇ 4H 2 O 2 + Na 2 B 4 O 7 + 2NaOH (2)
  • the sodium perborate fulfills a dual function: On the one hand, borax and sodium hydroxide solution can stabilize the pH of the dyebath in the desired dyeing range.
  • the buffer capacity of borax is based on a hydrolytic cleavage to a low-water polyboric acid. In the following reaction scheme it is clear that in the presence of borax and sodium hydroxide equilibrium is generated. When sodium hydroxide solution is used to saponify oligomers, further borax can be split, ie the pH is maintained: Na 2 B 4 O 7 + (1 + x) H 2 O ⁇ 2 B 2 O 3 • x H 2 O + 2OH - + 2Na + (3)
  • sodium perborate releases H 2 O 2 at the dyeing temperature and thus acts as an oxidizing agent, which counteracts reductive processes which can adversely affect the dyeing result in the alkaline.
  • a dehalogenation of the dyes is counteracted by heavy metals under reductive conditions.
  • the sodium perborate acts according to the invention as a dye stabilizer.
  • an oxidation of the dyes as it is for the purpose of regression of the color pigment, for example, in the dyeing of cellulose fibers with vat dyes, in frame the invention just avoided.
  • perborate Another advantage of the use of perborate is that the oxidizing agent is released only upon heating of the dyebath; Influences on the cold dyebath are thus excluded.
  • perborate salts with other cation partners is conceivable.
  • the selected buffer systems together have a sufficiently high capacity, are optimally suitable for the desired pH range (around pH 9.3), are ecologically harmless and can be used industrially.
  • the buffer mixture sodium chloride is added.
  • other ionic compounds can also be used for this purpose.
  • the NaCl has no direct influence on the buffering effect. In order to keep the clay concentration in the dyebath as low as possible and a precipitation of the dye To avoid NaCl is preferably added at most in a stoichiometric ratio to glycine.
  • NaCl is used in known dyeing processes, so that the dye from the dyeing liquor on the fiber by shifting the solubility equilibrium pulls or does not dissolve again in the liquor.
  • concentrations used for this purpose are well above those proposed in the context of the invention NaCl concentrations.
  • a sequestering agent comprising the essential constituents nitrilotriacetic acid and polycarboxylates is added to the dyebath.
  • This combined sequestering agent binds polyvalent metal ions and heavy metals as well as water hardness formers, which can negatively influence the dyeing result.
  • the sequestering agent with the essential constituents nitrilotriacetic acid and polycarboxylates has proven to be particularly effective in the pH range from 9 to 10, without a negative effect on the dyes (eg demetalization) or a precipitation of the dyes would be recorded.
  • nitrilotriacetic acid in the pH range of 9-12 has a sequestering effect of about 200 mg / l for Ca 2+ , whereas the optimal sequestering effect of about 300 mg / l for Fe 3+ is at pH 1.5-3.
  • a carboxylate having a sequestering effect of only about 60 mg / l for Ca 2+ at pH 8-10, but about 550 mg / l for Fe 3 at pH 9-12.
  • nitrilotriacetic acid is especially suitable for Ca 2+ ions
  • carboxylate is more suitable for sequestering Fe 3+ ions.
  • the use of the sequestering agent is preferably carried out in conjunction with the above-mentioned buffer system, but also isolated can already lead to a significant improvement of the dyeing result.
  • the initial pH of the dyeing process may range from about 9.3 to 9.4. In this pH range, the majority of available disperse dyes is still sufficiently stable.
  • the final pH of the dyeing process does not fall below the value 9.0. This is achieved by a corresponding buffer capacity. In this way precipitation of oligomers already in solution at the end of the dyeing process is reliably prevented, since below pH 9.0 the oligomers and their degradation products are no longer soluble at falling temperatures in the cooling process of the dyeing.
  • the concentration ratio of glycine to caustic soda (33%) in the buffer mixture may preferably be about 1.9 or less.
  • the amount of caustic soda solution should be adjusted to reach a starting pH of 9.3 to 9.4.
  • the amount of glycine determines the buffering capacity to compensate for alkali-consuming substances.
  • the concentration ratio of glycine to sodium chloride is preferably about 1.3.
  • the invention proposes a dyeing auxiliaries which contains glycine or a glycine derivative, a lye and a perborate salt.
  • the lye - preferably sodium hydroxide - can of course also be added separately before the dyeing process.
  • the dyeing process according to the invention is suitable both for pure polyester fibers and for mixed fibers, e.g. Polyester / cellulose fiber mixtures suitable.
  • the textile material is dyed with a conventional high-temperature dyeing process at about 130 C in a dyeing machine. Subsequently, only a hot rinse is required. In order to a reproducible coloration is produced with technologically improved textile material.
  • the reference dyeing, as well as the alkaline dyeings are carried out on polyester crepe knit.
  • the acid dyeing is carried out using 1 g / l Setamol WS (brand name manufacturer BASF AG, Ludwigshafen) and pH 4.5 by adjustment with acetic acid.
  • the colorimetric evaluation of the color difference is represented by the CIELAB values Delta C and Delta H.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Claims (11)

  1. Procédé de teinture de matériaux textiles comportant des fibres de polyester, dans lequel le matériau textile est traitée dans un bain de teinture alcalin contenant un colorant de dispersion à une température supérieure à 100°C, caractérisé en ce que l'ajustement de la valeur de pH du bain de teinture est réalisé par ajout d'un mélange tampon composé au moins de glycine et/ou d'un dérivé de glycine et d'une lessive avant le début du procédé de teinture, et en ce que l'on ajoute un sel de perborate au bain de teinture.
  2. Procédé selon la revendication 1, caractérisé en ce que la valeur de pH du bain de teinture est ajustée avant le début du procédé de teinture par ajout au départ d'un mélange tampon de glycine et de lessive de soude caustique, et en ce que l'on ajoute au bain de teinture avant le début du procédé de teinture du perborate de sodium, si bien que la valeur de pH est maintenue essentiellement constante du début jusqu'à la fin du procédé de teinture.
  3. Procédé selon la revendication 1 ou 2, caractérisé en ce que l'on ajoute au mélange tampon du chlorure de sodium.
  4. Procédé selon l'une des revendications 1 à 3, caractérisé en ce que l'on ajoute au bain de teinture un agent séquestrant ayant comme composants essentiels de l'acide nitrilotriacétique et des polycarboxylates.
  5. Procédé selon l'une des revendications 1 à 4, caractérisé en ce que la valeur de pH de départ du procédé de teinture est comprise dans la gamme d'environ 9,3 à 9,4.
  6. Procédé selon l'une des revendications 1 à 5, caractérisé en ce que la valeur de pH finale du procédé de teinture n'est pas inférieure à 9,0.
  7. Procédé selon l'une des revendications 2 à 6, caractérisé en ce que le rapport de concentration entre la glycine et la lessive de soude caustique (33 %) dans le mélange tampon est d'environ 1,9 ou moins.
  8. Procédé selon l'une des revendications 2 à 7, caractérisé en ce que la concentration du perborate de sodium dans le bain de teinture est d'environ 0,1 g/l.
  9. Procédé selon l'une des revendications 2 à 8, caractérisé en ce que le rapport de concentration entre la glycine et le chlorure de sodium est d'environ 1,3.
  10. Adjuvant de teinture pour teinture alcaline de matériaux textiles comportant des fibres de polyester avec un colorant de dispersion à une température supérieure à 100 °C, caractérisé en ce que l'adjuvant de teinture comprend de la glycine et/ou un dérivé de glycine et une lessive, ainsi qu'un sel de perborate et un agent séquestrant ayant comme composants essentiels de l'acide nitrilotriacétique et des polycarboxylates.
  11. Utilisation d'un adjuvant de teinture pour la teinture alcaline de matériaux textiles comportant des fibres de polyester avec un colorant de dispersion à une température supérieure à 100 °C, caractérisée en ce que l'adjuvant de teinture comprend de la glycine et/ou un dérivé de glycine et une lessive, ainsi qu'un sel de perborate.
EP98122283A 1997-12-15 1998-11-24 Procédé de teinture de matériaux textiles comprenant des fibres de polyester Expired - Lifetime EP0924334B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19755647 1997-12-15
DE19755647A DE19755647A1 (de) 1997-12-15 1997-12-15 Verfahren zum Färben von Polyesterfasern aufweisendem Textilgut

Publications (3)

Publication Number Publication Date
EP0924334A2 EP0924334A2 (fr) 1999-06-23
EP0924334A3 EP0924334A3 (fr) 2000-11-22
EP0924334B1 true EP0924334B1 (fr) 2006-05-31

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP98122283A Expired - Lifetime EP0924334B1 (fr) 1997-12-15 1998-11-24 Procédé de teinture de matériaux textiles comprenant des fibres de polyester

Country Status (6)

Country Link
US (1) US6004357A (fr)
EP (1) EP0924334B1 (fr)
JP (1) JPH11241279A (fr)
AT (1) ATE328151T1 (fr)
BR (1) BR9805442A (fr)
DE (2) DE19755647A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SI21189A (sl) * 2002-03-25 2003-10-31 Univerza V Ljubljani, Metoda predobdelave poliestra za znižanje izločanja oligomerov pri visokotemperaturnem kislem barvanju z disperzijskimi barvili
US6911421B2 (en) * 2002-11-01 2005-06-28 Nicca Usa, Inc. Surfactant blends for removing oligomer deposits from polyester fibers and polyester processing equipment
KR100848220B1 (ko) 2007-04-27 2008-07-24 손병철 폴리에스테르 염색용 다기능 분산제
CN103044964A (zh) * 2012-12-11 2013-04-17 苏州大学 染料组合物及其用于聚酯纤维织物碱性染色的方法
CN105113283A (zh) * 2015-09-14 2015-12-02 广东溢达纺织有限公司 涤纶棉混纺织物的染色方法
CN109295753A (zh) * 2018-09-27 2019-02-01 桐乡市创新纺织有限公司 一种涤纶纤维的染色工艺

Family Cites Families (7)

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Publication number Priority date Publication date Assignee Title
GB887386A (en) * 1957-06-14 1962-01-17 Gen Aniline & Film Corp Metallizing azoic dyeings
IT1101601B (it) * 1977-07-05 1985-10-07 Hoechst Ag Processo per proteggere coloranti sensibili alla riduzione da una riduzione durante la stampa e la tintura al foulard su materiali fibrosi sintetici, materiali cellulosici e loro miscele
US4509992A (en) * 1982-01-18 1985-04-09 Parker Chemical Company Processes and compositions for the treatment of aluminum surfaces
US5019133A (en) * 1988-11-25 1991-05-28 Mitsubishi Kasei Corporation Method for dyeing polyester-containing fibers in an alkaline dyeing bath and dyeing assistant, an amino-acid compound
DE4133995A1 (de) * 1990-10-17 1992-04-23 Ciba Geigy Ag Verfahren zum faerben von mischfasern aus cellulosehaltigen fasermaterialien und hydrophoben fasermaterialien
JP3089066B2 (ja) * 1991-11-18 2000-09-18 ダイスタージャパン株式会社 ポリエステル繊維の染色法
JP3221752B2 (ja) * 1992-10-28 2001-10-22 ダイスタージャパン株式会社 ポリエステル、コットン混合繊維の染色方法

Also Published As

Publication number Publication date
EP0924334A3 (fr) 2000-11-22
BR9805442A (pt) 1999-11-03
EP0924334A2 (fr) 1999-06-23
ATE328151T1 (de) 2006-06-15
JPH11241279A (ja) 1999-09-07
DE19755647A1 (de) 1999-06-24
DE59813571D1 (de) 2006-07-06
US6004357A (en) 1999-12-21

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