EP0000898B1 - Egalisiermittel und Verfahren zum Färben von synthetischen Fasermaterialien - Google Patents

Egalisiermittel und Verfahren zum Färben von synthetischen Fasermaterialien Download PDF

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Publication number
EP0000898B1
EP0000898B1 EP78100620A EP78100620A EP0000898B1 EP 0000898 B1 EP0000898 B1 EP 0000898B1 EP 78100620 A EP78100620 A EP 78100620A EP 78100620 A EP78100620 A EP 78100620A EP 0000898 B1 EP0000898 B1 EP 0000898B1
Authority
EP
European Patent Office
Prior art keywords
polyester
levelling agent
acid
mol
agent according
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
Application number
EP78100620A
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German (de)
English (en)
French (fr)
Other versions
EP0000898A1 (de
Inventor
Gerhard Dr. Weckler
Hans Joachim Hauss
Karl Dr. Hintermeier
Fritz Dr. Engelhardt
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.)
Sanofi Aventis Deutschland GmbH
Original Assignee
Cassella AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Cassella AG filed Critical Cassella AG
Publication of EP0000898A1 publication Critical patent/EP0000898A1/de
Application granted granted Critical
Publication of EP0000898B1 publication Critical patent/EP0000898B1/de
Expired 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
    • C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
    • C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/6886—Dicarboxylic acids and dihydroxy compounds
    • 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
    • D06P1/52—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 synthetic macromolecular substances
    • D06P1/5264—Macromolecular compounds obtained otherwise than by reactions involving only unsaturated carbon-to-carbon bonds
    • D06P1/5271—Polyesters; Polycarbonates; Alkyd resins

Definitions

  • the invention relates to a leveling agent and a method for uniformly dyeing materials made of synthetic fibers, such as e.g. Fibers made from cellulose triacetate, polyurethane, polyamides, but in particular from fibers made from linear polyesters and their mixtures with natural fibers with disperse dyes.
  • synthetic fibers such as e.g. Fibers made from cellulose triacetate, polyurethane, polyamides, but in particular from fibers made from linear polyesters and their mixtures with natural fibers with disperse dyes.
  • a water-soluble or dispersible branched, sulfonate group-containing polyester having a molecular weight of 600 to 5000, based on 100 mol -% of the polycarboxylic acid component, 1 to 40 mol% of branching components, ie
  • branching components ie
  • tricarboxylic acids, tetracarboxylic acids, trial alcohols or tetra alcohols can be used.
  • the water-soluble or water-dispersible linear polyesters can be prepared in a manner known per se by polycondensation of 100 mol% of dicarboxylic acids with 90 to 120 mol% of diols, a total of 5 to 40 mol%, preferably 5 to 30 mol% of the Dicarboxylic acids and / or the dihydroxy compounds must carry sulfo groups in the form of salts.
  • Saturated and unsaturated aliphatic, cycloaliphatic, araliphatic or aromatic dicarboxylic acids can be used as dicarboxylic acids.
  • Dicarboxylic acids with 4 to 10 carbon atoms are preferred, especially the benzene dicarboxylic acids.
  • suitable dicarboxylic acids are: succinic acid, glutaric acid, adipic acid, suberic acid, maleic acid, fumaric acid, itaconic acid, cyclohexanedicarboxylic acid 1,4, cyclohexanedicarboxylic acid 1,3, phthalic acid, isophthalic acid, terephthalic acid, the naphthalenedicarboxylic acids, e.g.
  • 1,4-naphthalenedicarboxylic acid 1,5-naphthalenedicarboxylic acid, also diphenic acid, norbornane dicarboxylic acid etc.
  • dicarboxylic acids their derivatives, such as anhydrides, acid halides, especially acid chlorides, esters, especially those with readily distillable alcohols having 1 to 4 carbon atoms, be used.
  • esters, anhydrides and acid chlorides are, for example: dimethyl terephthalate, diethyl terephthalate, diperephthalate terephthalate, de-isopropyl terephthalate, dimethyl terephthalate, dimethyl isophthalate, di-isophthalate, isophthalate, di-isophthalate Diethyl phthalate, dipropyl phthalate, diisopropyl phthalate, dibutyl phthalate, dimethyl, dimethyl, diethyl, dipropyl or dibutyl malate, dimethyl or dibutyl succinate, diethyl glutarate or -diisopropyl ester, adipic acid-diethyl- or -di-isobutyl ester, pimelic acid-dimethyl-, -diisopropyl- or -di
  • Suitable esters can also be those with the diols listed below as the alcohol component.
  • Suitable diols for the linear polycondensates to be used according to the invention are saturated, unsaturated aliphatic, cycloaliphatic and araliphatic compounds, preferably those having 2 to 10 carbon atoms, especially saturated aliphatic, cycloaliphatic or araliphatic compounds with ether bridges.
  • the indicated preferred range of 2 to 10 carbon atoms relates only to each of the aliphatic parts between 2 ether bridges or oxygen atoms.
  • diols examples include: ethylene glycol, 1,2-propanediol and 1,3-propanediol, ethylene glycol mono- (3-hydroxy-propyl) ether, ethylene glycol mono- (3-hydroxy-propyl-2) ether, ethylene glycol mono- (2-hydroxypropyl) ether, butanediols, in particular 1,4-butanediol, pentanediols, such as 1,5-pentanediol, hexanediols, in particular 1,6-hexanediol, decanedio) -1.10, diethylene glycol, dipropylene glycol, bis (3-hydroxypropyl) ether, triethylene glycol, tetraethylene glycol, tripropylene glycol, 4,8-dioxadecane-1,10-diol, polyethylene glycols with a molecular weight of 300 to 2000, polypropylene glycols
  • the preferred diol component is diethylene glycol, and also triethylene glycol.
  • the diols can also expediently be used as mixtures, e.g. can be used as a mixture of diethylene and triethylene glycol.
  • Other preferred mixtures contain 40 to 95 mol% of diethylene and / or triethylene glycol and 5 to 60 mol% of other diols, especially those with more than 2 ether bridges and particularly advantageously polyethylene glycol with an average molecular weight of 300 to 1000.
  • dicarboxylic acids and the diols can be replaced by hydroxycarboxylic acids, which preferably contain 2 to 11 carbon atoms.
  • Suitable hydroxycarboxylic acids are: glycolic acid, lactic acid, 3-hydroxypropionic acid, 4-hydroxybutyric acid, 5-hydroxypenten-3-acid, mandelic acid, 3-hydroxymethylcyclohexane carboxylic acid, 4-hydroxymethyl cyclohexane carboxylic acid, 6-hydroxymethyl decalin carboxylic acid (-2 ). 3-hydroxyethyl benzoic acid,
  • Esters Derivatives of hydroxycarboxylic acids, e.g. Esters can be used.
  • esters of hydroxycarboxylic acids are: lactic acid methyl ester, lactic acid ethyl ester, 4-hydroxybutyric acid methyl ester, mandelic acid ethyl ester,
  • hydroxycarboxylic acids or their derivatives are used, preferably at most 40 mol% of the dicarboxylic acid and diol content are replaced by hydroxycarboxylic acids or their derivatives.
  • Aliphatic, cycloaliphatic or aromatic dicarboxylic acids, aliphatic, cycloaliphatic or araliphatic diols, hydroxycarboxylic acids and, as far as it can be, as building blocks that carry sulfo groups in the form of salts, especially in the form of alkali, ammonium, substituted ammonium or triethanolammonium salts are carboxylic acids, also their derivatives, in particular esters, are used.
  • sulfonato-containing hydroxycarboxylic acids or their esters 5-sodium sulfonatosalicylic acid, 5-sodium sulfonato-benzoic acid methyl ester,
  • sulfonato-containing diols or ethoxylated diphenols are also suitable:
  • Disodium-3,6-disulfonato-2,7-dihydroxynaphthalene disodium-3,6-disulfonato-1,8-dihydroxynaphthalene.
  • a variation of the above general formula is that 0 to 40 mol% of the total proportion of benzenedicarboxylic acids in the formula is replaced by an aliphatic or cycloaliphatic dicarboxylic acid having 4 to 10 carbon atoms.
  • linear polyesters which are preferred for the production of the leveling agent according to the invention, branched, water-soluble or water-dispersible polyesters can also be used, which are produced in principle like the aforementioned linear polyesters, only at least one branching component must be used in their production will.
  • polycarboxylic acids with 3, 4 or 5, preferably 3 or 4 carboxyl groups, the polyhydroxy compounds or the hydroxycarboxylic acids mentioned under c) can optionally carry an S0 3 M group, where M is an alkali metal or ammonium.
  • Suitable branching polycarboxylic acids or their derivatives include: trimellitic acid, trimesic acid, hemimellitic acid, mellophanic acid, prehnitic acid, pyromellitic acid, aconitic acid, tricarballylic acid, ⁇ thantetracarbonTalkre, trimellitic anhydride, pyromellitic dianhydride, Hemimeilithklareanhydrid, Mellophanklahydrid, Prehnitklareanhydrid, trimethyl trimellitate, Trimellithklathylester, Trimesinklaretrimethylester, Hemimellithkladretrimethylester, meii6ppur- acid tetramethyl ester, prehnitic acid tetramethyl ester, pyromellitic acid tetramethyl ester, pyromellitic acid tetraethyl ester, 1,2,3-cyclohexane tricarboxylic acid, 1,2,4
  • Suitable polyhydroxy compounds are e.g. For example: glycerin, erythritol, pentaerythritol, trimethylolpropane, trimethylolethane.
  • Suitable branching hydroxycarboxylic acids or their derivatives are e.g. As citric acid, malic acid, tartaric acid, trimethyl citrate, dimethyl malate, dimethyl tartar.
  • those branched water-soluble or water-dispersible polyesters which contain 1 to 40 mol%, preferably 5 to 40 mol%, of branching components, based on 100 mol% of the components containing caboxyl groups.
  • the dicarboxylic acid components present, at least 40 mol% preferably also consist of benzenedicarboxylic acids, in particular isophthalic acid.
  • the compounds of the components carrying hydroxyl groups are selected so that, based on 100 mol% of the diols and polyols, they consist of at least 40 mol% of diethylene glycol and / or triethylene glycol.
  • the required water-soluble or water-dispersible linear or branched polyesters containing sulfonate groups can also be obtained by introducing the water-solubilizing sulfonate groups into correspondingly unsaturated polyesters by, for. B. according to DT-OS 23 35 480 bisulfite on polyester containing double bonds.
  • the apparent average molecular weight is determined in a vapor pressure osmometer in dimethylformamide as the solvent.
  • the real average molecular weight is higher than the apparent value measured in this way.
  • the measured value is a sufficiently precise criterion for characterizing the degree of condensation of the poly-mixed esters according to the invention and for determining the end product of the condensation.
  • the ethoxylation products of castor oil required to produce the leveling agent according to the invention are in part commercially available as emulsifiers and are obtained in a manner known per se by reacting castor oil with 5 to 50 moles of ethylene oxide.
  • the leveling agent according to the invention is produced by simply uniformly mixing the polyester component A with the ethoxylation product B in a weight ratio of 1: (0.1 to 5), preferably 1: (0.5 to 2). After components A and B have been mixed, the pH is usually slightly acidic. It is useful to adjust the pH of the leveling agent by stirring in an inorganic or organic base, such as. B. sodium hydroxide solution to a pH of 6 to 7. All or part of the COOH groups present are converted into the corresponding salts COOM, where M is the cation of the base, preferably an alkali metal or ammonium.
  • the leveling agent according to the invention can also be used in the form of a solution, for example in the form of a 10 to 50% by weight, preferably 10 to 30% by weight, aqueous solution.
  • the dyeing process according to the invention can be used to uniformly dye materials made from all synthetic fibers, but preferably fibers from linear polyesters, which can be dyed with water-insoluble disperse dyes by the customary HT exhaust process.
  • the dyeing process according to the invention is also suitable for dye combinations which are difficult to handle in the case of textured material, in the case of bobbins and in the rapid dyeing process. Disruptions to fleet stability, filtering, irregularities, tone shifts and the like are prevented with a high degree of certainty.
  • the addition of the ethoxylation product produces a synergistic effect, so that considerably less of the relatively expensive polyester has to be used. Rapid dyeing processes give particularly good results. In such rapid dyeing processes, the goods to be dyed are suddenly offered relatively large amounts of dye at temperatures of approximately 130 ° C. The resulting risk of irregularities is avoided by using the leveling agent according to the invention.
  • the dye baths are prepared in the customary manner at 50 to 60 ° C. and adjusted to pH 4 to 6 by means of pH-regulating substances.
  • the leveling agent according to the invention is optionally added in the form of a solution, in amounts of 0.02 g / 1 to 5 g / I, preferably 0.05 g / I to 2 g / I (based on 100% leveling agent).
  • the predispersed, water-insoluble disperse dye and the material to be colored are then added and heated to the required dyeing temperature (temperatures up to approx. 130 ° C.) and the usual dyeing time is long.
  • the dyeings are finished in a known manner, e.g. through reductive aftertreatment.
  • the liquor is produced separately from the material to be colored with the addition of the polycondensate according to the invention.
  • the liquor, heated to the dyeing temperature of 120 to 130 ° C, is then quickly brought into contact with the material to be dyed. If the so-called sluice technique is used, this can be fiction appropriate polycondensation product are also added to the dyebath before adding the dye dispersion.
  • Polycondensation product can also be added to the dyebath before adding the dye dispersion.
  • Example 2 The same product as in Example 1 is also obtained if the polyester melt of Example 1 is diluted with water to 1900 g of a 20% strength solution, neutralized and then 380 g of the commercially available adduct of 30 moles of ethylene oxide and 1 mole of castor oil are stirred in and homogeneously distributed .
  • Example 1 A similarly effective product is obtained if, in Example 1, instead of the addition product of 30 mol AEO to 1 mol castor oil, the same amount by weight of an addition product of 50 mol AEO to 1 mol castor oil is used.
  • Example 1 A similarly effective product is obtained if, in Example 1, instead of the addition product of 30 mol AEO to 1 mol castor oil, the same amount by weight of an addition product of 15 mol AEO to 1 mol castor oil is used.
  • a clearly detectable improvement in the leveling effect can also be obtained by adding only 76 g of the addition product of 30 mol AEO to 1 mol castor oil in Example 2, which gives a 23% solution, based on the solids content.
  • Example 2 An even better leveling product than in Example 1 is obtained if 2 760 g of the adduct of 30 moles of AEO and 1 mole of castor oil are used in Example 1, the concentration, based on the solids content, increasing to approximately 43%.
  • a very good leveling product is also obtained if, in Example 1, 1900 g of the adduct of 30 moles of AEO and 1 mole of castor oil are added instead of 380 g.
  • Example 9 The same product as in Example 9 can also be obtained if the 328 g of polyester melt is first diluted with 1312 ml of water to give a clear, amber-colored, 20% solution, neutralized with sodium hydroxide solution and subsequently 328 g of the addition product of 30 mol of AEO to 1 MOI castor oil is stirred in homogeneously.
  • Muffles made of textured polyester yarns are flowed through on a HT dyeing machine at a liquor ratio of 1:10 with a liquor of 130 ° C. which consists of soft water of pH 4.5 (adjusted with acetic acid) and an addition of 1 , 5 g / l of a leveling agent according to the invention.
  • the leveling agent consists of a linear, water-soluble polyester with a molecular weight of 2500, which according to Example 1 consists of polycondensation was prepared and the same amount by weight of an adduct of 30 moles of AEO and 1 mole of castor oil was mixed. The mixture was diluted with water as described in Example 1.
  • the flow rate through the muff is 20 I / kg per minute. After 30 minutes of treatment at 130 ° C., the mixture is cooled, the liquor is drained and the colored material is reductively cleaned.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Coloring (AREA)
EP78100620A 1977-08-18 1978-08-07 Egalisiermittel und Verfahren zum Färben von synthetischen Fasermaterialien Expired EP0000898B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2737260 1977-08-18
DE19772737260 DE2737260A1 (de) 1977-08-18 1977-08-18 Egalisiermittel und verfahren zum gleichmaessigen faerben von materialien aus synthesefasern

Publications (2)

Publication Number Publication Date
EP0000898A1 EP0000898A1 (de) 1979-03-07
EP0000898B1 true EP0000898B1 (de) 1982-02-03

Family

ID=6016731

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100620A Expired EP0000898B1 (de) 1977-08-18 1978-08-07 Egalisiermittel und Verfahren zum Färben von synthetischen Fasermaterialien

Country Status (4)

Country Link
EP (1) EP0000898B1 (enrdf_load_stackoverflow)
JP (1) JPS5442475A (enrdf_load_stackoverflow)
DE (2) DE2737260A1 (enrdf_load_stackoverflow)
IT (1) IT1118248B (enrdf_load_stackoverflow)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57131672A (en) * 1981-02-06 1982-08-14 Mitsubishi Heavy Ind Ltd Cable traction device
JPS5928461U (ja) * 1982-08-11 1984-02-22 東京製綱株式会社 より線の引抜装置
US4729925A (en) * 1986-12-22 1988-03-08 Eastman Kodak Company Polyurethane elastomers comprising a charge-control agent and shaped elements therefrom
EP1070781A1 (de) * 1999-07-19 2001-01-24 Clariant International Ltd. Erhöhung der Nassgleitfähigkeit von Textilmaterial und Nassgleitmittel dafür
EP1094147A1 (de) 1999-09-22 2001-04-25 Clariant International Ltd. Erhöhung der Nassgleitfähigkeit von Textilmaterial und Nassgleitmittel dafür
EP1273102B1 (en) * 2000-04-04 2005-11-16 Koninklijke Philips Electronics N.V. A digital to analog converter
JP4614912B2 (ja) * 2006-05-16 2011-01-19 日華化学株式会社 ポリエステル系繊維材料用オリゴマー除去剤
BR102018077399A8 (pt) * 2018-12-28 2021-06-15 Suzano Papel E Celulose S A resinas fenólicas do tipo resol, processo de síntese das referidas resinas e uso das mesmas
CN114575170B (zh) * 2022-03-15 2023-10-03 浙江联胜新材股份有限公司 一种涤纶染色高温匀染剂的制备方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1619489C3 (de) * 1966-09-09 1975-03-06 Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt Emulgiermittel für wasserunlösliche Carrier für das Färben und Bedrucken von synthetischen Fasern
CH575442A5 (enrdf_load_stackoverflow) * 1974-02-26 1976-05-14 Ciba Geigy Ag
DE2508472C3 (de) * 1975-02-27 1980-08-28 Hoechst Ag, 6000 Frankfurt Verfahren zum gleichmäßigen Färben von Fasermaterialien aus linearen Polyestern
DE2621653A1 (de) * 1976-05-15 1977-12-01 Cassella Farbwerke Mainkur Ag In wasser loesliche oder dispergierbare, verzweigte copolyester und verfahren zu ihrer herstellung
DE2653284C3 (de) * 1976-11-24 1979-05-03 Hoechst Ag, 6000 Frankfurt Verfahren zum gleichmäßigen Färben von synthetischen Fasermaterialien

Also Published As

Publication number Publication date
IT1118248B (it) 1986-02-24
IT7826798A0 (it) 1978-08-17
JPS5442475A (en) 1979-04-04
DE2861600D1 (en) 1982-03-11
EP0000898A1 (de) 1979-03-07
DE2737260A1 (de) 1979-07-12
JPS6151073B2 (enrdf_load_stackoverflow) 1986-11-07

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