EP0364792B1 - Carrier pour la teinture de matériaux en polyester - Google Patents

Carrier pour la teinture de matériaux en polyester Download PDF

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Publication number
EP0364792B1
EP0364792B1 EP89118113A EP89118113A EP0364792B1 EP 0364792 B1 EP0364792 B1 EP 0364792B1 EP 89118113 A EP89118113 A EP 89118113A EP 89118113 A EP89118113 A EP 89118113A EP 0364792 B1 EP0364792 B1 EP 0364792B1
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EP
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Prior art keywords
weight
alkyl
carrier
mol
denotes
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.)
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Application number
EP89118113A
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German (de)
English (en)
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EP0364792A2 (fr
EP0364792A3 (fr
Inventor
Frank Dr. Bartkowiak
Hans Dr. Schulze
Wolf-Dieter Dr. Schröer
Günther Dr. Boehmke
Karlhans Dipl.-Ing. Jakobs
Willi Dr. Schössler
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.)
Bayer AG
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Bayer AG
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Publication of EP0364792A3 publication Critical patent/EP0364792A3/fr
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Publication of EP0364792B1 publication Critical patent/EP0364792B1/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
    • D06P1/64—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
    • D06P1/65118—Compounds containing hydroxyl 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
    • D06P1/642—Compounds containing nitrogen
    • D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
    • D06P1/6495—Compounds containing carbonamide -RCON= (R=H or hydrocarbons)
    • D06P1/6498—Compounds containing -CONCO-, e.g. phthalimides, hydantoine; Compounds containing RCONHSO2R (R=H or hydrocarbon)
    • 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
    • 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 carriers, their preparations and processes for dyeing polyester materials with disperse dyes in the presence of these carriers.
  • Known carriers used in textile practice for dyeing polyester include halogenobenzenes, halogen toluenes, N-alkylphthalimides, aromatic carboxylic acid esters, methylnaphthalene, diphenyl, diphenyl ether, naphthol ether, phenol ether and oxydiphenyls.
  • these connections have disadvantages. All compounds, with the exception of the N-alkylphthalimides, have a strong intrinsic odor. Methylnaphthalene and the oxydiphenyls adversely affect the lightfastness of the dyeings. Diphenyl ether has the disadvantage that its carrier activity depends strongly on the constitution of the disperse dye used and therefore often no reproducible colorations are obtained.
  • N-alkylphthalimides show a sharp drop in the dyeing temperature below 98 ° C. Carrier effect, which limits their use in higher regions, where this temperature is not reached with open dyeing machines. Phthalic acid esters and benzoic acid esters have only a limited carrier effect and a limited leveling capacity and therefore require high amounts.
  • the object of the present invention is to provide highly effective, halogen-free carriers which bring about the most level possible coloring with a small amount used.
  • the dyeing obtained should meet high authenticity requirements, and the dyeing of mixed fibers should not result in soiling of the accompanying fiber.
  • the carriers according to the invention are a mixture of N-alkylphthalimides (I) and compounds of the general formula wherein R is C1-C7 alkyl; Phenyl, benzyl or phenylethyl, which can be substituted by C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkoxycarbonyl.
  • R1 is hydrogen, C1-C4-alkyl, C1-C4-alkylcarbonyloxy, hydroxy or C1-C4-alkoxycarbonyl, m 0 or 1, n is 0 or 1, where m and n are not simultaneously 0, contain, is solved.
  • These mixtures of carrier active substances show a synergistic increase in the color-accelerating effect compared to the individual components.
  • the preferred weight ratio of N-alkylphthalimides (I) to the compounds (II) is 0.5-12: 1.
  • the carrier mixtures according to the invention are water-insoluble, they are preferably added to the dyeing liquors in the form of preparations which contain emulsifiers or dispersants and, if appropriate, solvents.
  • N-alkylphthalimides (I) are understood to mean, in particular, straight-chain or branched alkyl radicals (C1-C6) on the nitrogen-substituted phthalimides or mixtures thereof which, for. B. can be prepared by the reaction of phthalic anhydride or phthalic acid esters with amines.
  • the carriers can therefore contain phthalic acid amides and esters due to the manufacturing process.
  • Examples of the compounds (II) are aromatic monocarboxylic acid esters (e.g. esters of benzoic acid, methylbenzoic acid, salicylic acid), dicarboxylic acid esters (e.g. esters of terephthalic acid or phthalic acid), carbonates (e.g. diphenyl carbonate) and ethers (e.g. B. diphenyl ether or ditolyether).
  • aromatic monocarboxylic acid esters e.g. esters of benzoic acid, methylbenzoic acid, salicylic acid
  • dicarboxylic acid esters e.g. esters of terephthalic acid or phthalic acid
  • carbonates e.g. diphenyl carbonate
  • ethers e.g. B. diphenyl ether or ditolyether.
  • alcohol components of the esters such. B. C1-C6 alkanols, phenols and benzyl alcohol.
  • Nonionic and anionic emulsifiers are preferred as emulsifiers 3.).
  • emulsifiers are mixtures of a) ethoxylated oils, such as castor oil or soybean oil, ethoxylated alcohols, alkylphenol polyglycol ethers or phenylalkylphenol polyglycol ethers, b) alkali metal, alkaline earth metal and / or ammonium salts of organic sulphonic acids having at least 10 carbon atoms, such as dodecylbenzenesulfonic acid, diodecylbenzenesulphonic acid, and dodecylbenzenesulphonic acid -Sulfo fatty acids and ricinoleyl methyl tauride.
  • ethoxylated oils such as castor oil or soybean oil, ethoxylated alcohols, alkylphenol polyglycol ethers or phenylalkylphenol polyglycol ethers
  • z. B. alkanols, glycols, ketones, N-substituted caprolactams or ethers can be used.
  • the carrier mixtures according to the invention are well compatible with other carriers, they can also be used in a mixture with known other carriers.
  • the disperse dyes used for dyeing are the disperse dyes usually used for dyeing polyesters, as described, for example, in "Color Index” Vol. 2, pp. 2483-2741, 3rd edition (1971).
  • the dyeing in the presence of the carriers according to the invention is carried out according to the batchwise methods customary for dyeing with disperse dyes; the usual process operating at 98 ° C. and the high-temperature process may be mentioned as such.
  • the carrier blends according to the invention are also suitable for dyeing polyester / wool and polyester / cotton blended fabrics, because when they are used the soiling of the wool and cotton content is avoided by the disperse dyes.
  • the dyeing can be carried out at temperatures of 90-140 ° C, the preferred industrial application being at 90-150 ° C.
  • An additional advantage of the carrier settings described is the very good effectiveness below cooking temperature, which pure N-alkyl phthalimide carriers do not show, e.g. B. at 95 ° C, which is often not exceeded under practical conditions with open dyeing machines.
  • the amounts of the mixture of carriers (I) and (II) required to carry out the dyeing can easily be determined from case to case by preliminary tests. In general, amounts of 1 to 7 g per liter of dye liquor have proven themselves in the usual liquor ratios of 1: 5 to 1:40.
  • components (I) and (II) as carriers in dyeing polyester are known.
  • DE-C-1 769 210 So z. B. the use of N-alkylphthalimides in DE-C-1 769 210, the use of phthalic acid esters in US-A-4 032 291 and the use of benzoic acid esters in DE-A-2 348 363.
  • DE-C-1 769 210 also discloses the use of mixtures of N-alkylphthalimides with disubstituted benzoic acid esters.
  • the mixtures according to the invention have a higher color-accelerating effect than corresponds to the sum of the individual effects.
  • This synergistic increase in the effectiveness is not shown by the mixtures known hitherto (for example the mixtures of N-alkylphthalimides described in DE-C-1 769 210 with salicylic acid compounds containing alkyl groups).
  • the mixing ratio at which the synergistic optimum is present depends on the components of the carrier mixtures and can easily be determined in individual cases by preliminary tests.
  • the pH of the bath is adjusted to pH 4.5-5 with acetic acid.
  • the bath is then heated to 98 ° C. and held at this temperature for 60 minutes. A uniform blue color is obtained.
  • the carrier effectiveness of the carrier mixtures of Examples 1-12 is determined by comparing the color depths achieved.
  • the small amounts of the mixtures demonstrate their more advantageous carrier activity compared to the individual components.
  • this mixture shows no synergistic increase in carrier effectiveness compared to the individual components.
  • the pH of the bath is adjusted to pH 4.5-5 with acetic acid.
  • the dye liquor is then brought to the boiling temperature and kept at this temperature for one hour. A full, even red color is achieved.
  • Polyester staple fibers are introduced in a liquor ratio of 1:15 into a dyeing liquor containing 1 g of a disperse dye according to Example 14 per liter, 0.03 g of a dye according to the Color Index, 2nd edition (1956) Volume 3, No. 12790, 2nd g of a condensation product of naphthalene sulfonate and formaldehyde, 2 g of sodium dihydrogen phosphate and 3.5 g of a carrier setting of Example 14.
  • the pH of the bath is adjusted to pH 4.5-5 with acetic acid.
  • the liquor is slowly heated to 98 ° C. and treated at this temperature for one hour. A dark reddish brown color is obtained.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Indole Compounds (AREA)

Claims (5)

  1. Mélange de véhiculeurs, qui contient des N-alkylphtalimides (I) et des composés de formule générale
    Figure imgb0009
     dans laquelle
    R est un groupe alkyle en C₁ à C₇ ; phényle, benzyle ou phényléthyle qui peuvent être substitués par un radical alkyle en C₁ à C₄, alkoxy en C₁ à C₄ ou alkoxycarbonyle en C₁ à C₄,
    R¹ est l'hydrogène, un groupe alkyle en C₁ à C₄, alkylcarbonyloxy en C₁ à C₄, hydroxy ou alkoxycarbonyle en C₁ à C₄,
    m a la valeur 0 ou 1,
    n a la valeur 0 ou 1, m et n ne pouvant pas être en même temps égaux à 0.
  2. Mélange de véhiculeurs suivant la revendication 1, qui contient les composants (I) et (II) dans le rapport en poids de 0,5-12:1.
  3. Mélange de véhiculeurs suivant la revendication 1, qui contient
    1.) 40 à 90 % en poids de (I),
    2.) 8 à 58 % en poids de (II),
    3.) 2 à 30 % en poids d'un émulsionnant et
    4.) 0 à 10 % en poids de solvant.
  4. Mélange de véhiculeurs suivant la revendication 1, qui contient
    1.) 50 à 75 % en poids d'un N-alkylphtalimide portant un reste alkyle à chaîne droite ou ramifiée ayant 3 à 5 atomes de carbone,
    2.) 10 à 40 % en poids d'un ester d'alkyle en C₁ à C₄, de phényle ou de benzyle de l'acide benzoïque, méthylbenzoïque, téréphtalique, phtalique ou salicylique ou de carbonate de diphényle, d'éther de diphényle ou d'éther de ditolyle et
    3.) 5 à 20 % en poids d'un produit d'addition de 15 à 30 moles d'oxyde d'éthylène sur l'huile de ricin ou l'huile de soja, de 5 à 50 moles d'oxyde d'éthylène et/ou d'oxyde de propylène sur des alcools gras en C₁₆ à C₂₂, l'octylphénol ou le nonylphénol ou le phényléthylphénol, de sels de métaux alcalins, de métaux alcalino-terreux, d'ammonium ou de (di-) éthanolamine de l'acide dodécylbenzènesulfonique.
  5. Procédé de teinture de matières à base de polyesters avec des colorants dispersés en présence de mélanges de véhiculeurs suivant la revendication 1.
EP89118113A 1988-10-12 1989-09-29 Carrier pour la teinture de matériaux en polyester Expired - Lifetime EP0364792B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3834737 1988-10-12
DE3834737A DE3834737A1 (de) 1988-10-12 1988-10-12 Carrier fuer das faerben von polyestermaterialien

Publications (3)

Publication Number Publication Date
EP0364792A2 EP0364792A2 (fr) 1990-04-25
EP0364792A3 EP0364792A3 (fr) 1991-08-14
EP0364792B1 true EP0364792B1 (fr) 1993-02-03

Family

ID=6364951

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Application Number Title Priority Date Filing Date
EP89118113A Expired - Lifetime EP0364792B1 (fr) 1988-10-12 1989-09-29 Carrier pour la teinture de matériaux en polyester

Country Status (7)

Country Link
US (1) US4994089A (fr)
EP (1) EP0364792B1 (fr)
JP (1) JPH02169778A (fr)
AU (1) AU615581B2 (fr)
CA (1) CA2000411A1 (fr)
DE (2) DE3834737A1 (fr)
PT (1) PT91875B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011012598A1 (fr) 2009-07-31 2011-02-03 Basf Se Procédé de production de fibres de polyester aptes au filage et à la teinture

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2037597B1 (es) * 1990-08-27 1994-03-16 Sandoz Ag Perfeccionamientos en o relacionados con compuestos organicos.
WO1998038275A1 (fr) * 1997-02-28 1998-09-03 Sybron Chemicals Inc. Composition contenant de l'argile et procede destines au traitement d'une matiere textile
US5972049A (en) * 1998-01-28 1999-10-26 Sybron Chemicals Inc. Clay-containing dispersing composition for carriers used in the disperse dyeing of hydrophobic textiles
JP4721532B2 (ja) * 2001-02-21 2011-07-13 東レ株式会社 着色ポリフェニレンサルファイド繊維およびその製造方法
US6652602B2 (en) * 2001-12-21 2003-11-25 N.V. Bekaert S.A. Color dyeing system for plastic films
EP1348800B1 (fr) * 2002-03-19 2004-07-07 Dr. Th. Böhme KG Chem. Fabrik GmbH & Co. Utilisation d'alkyl-benzoates comme agents égalisants pour la teinture de matériaux fibreux en polyester
ATE305532T1 (de) * 2003-02-28 2005-10-15 Boehme Chem Fab Kg Egalisiermittel
US7092551B2 (en) * 2003-07-30 2006-08-15 Xerox Corporation System and method for measuring and quantizing document quality
JP4810224B2 (ja) * 2005-12-28 2011-11-09 共栄社化学株式会社 繊維製品洗浄剤
JP5629104B2 (ja) * 2010-03-24 2014-11-19 株式会社クラレ ポリエーテルイミド繊維の染色方法及びその染色物
US20120109279A1 (en) 2010-11-02 2012-05-03 Endologix, Inc. Apparatus and method of placement of a graft or graft system
ES2712744T3 (es) * 2010-12-16 2019-05-14 Toray Industries Agente de procesamiento para la estructura de fibra de poliéster y método de producción de la estructura de poliéster usando el mismo
CN107541968B (zh) * 2016-06-29 2020-04-24 苏州联胜化学有限公司 一种涤纶染色载体及其制备方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2881045A (en) * 1954-06-17 1959-04-07 American Cyanamid Co Method of dyeing synthetic fibrous materials
FR1140000A (fr) * 1955-01-05 1957-07-09 Hoechst Ag Procédé de teinture d'articles en fibres de polyesters à haut degré de polymérisation
DE1769210A1 (de) * 1968-04-20 1970-12-17 Bayer Ag Druck- und Faerbeverfahren
US4032291A (en) * 1976-01-12 1977-06-28 Ciba-Geigy Corporation Phenyl phthalate carriers in dyeing and printing synthetic fibers
EP0033715A1 (fr) * 1980-01-31 1981-08-12 Ciba-Geigy Ag Adjuvant et son utilisation pour la teinture ou l'azurage optique de matières textiles en polyester

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011012598A1 (fr) 2009-07-31 2011-02-03 Basf Se Procédé de production de fibres de polyester aptes au filage et à la teinture

Also Published As

Publication number Publication date
DE58903445D1 (de) 1993-03-18
AU615581B2 (en) 1991-10-03
AU4288989A (en) 1990-04-26
EP0364792A2 (fr) 1990-04-25
EP0364792A3 (fr) 1991-08-14
JPH02169778A (ja) 1990-06-29
US4994089A (en) 1991-02-19
DE3834737A1 (de) 1990-04-19
PT91875B (pt) 1995-07-06
CA2000411A1 (fr) 1990-04-12
PT91875A (pt) 1990-04-30

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