EP0616071A1 - Procédé de traitement de matériaux fibreux à l'aide de dérivés de la triazine - Google Patents

Procédé de traitement de matériaux fibreux à l'aide de dérivés de la triazine Download PDF

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Publication number
EP0616071A1
EP0616071A1 EP94102173A EP94102173A EP0616071A1 EP 0616071 A1 EP0616071 A1 EP 0616071A1 EP 94102173 A EP94102173 A EP 94102173A EP 94102173 A EP94102173 A EP 94102173A EP 0616071 A1 EP0616071 A1 EP 0616071A1
Authority
EP
European Patent Office
Prior art keywords
fiber materials
process according
formula
treatment
cyanuric chloride
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.)
Withdrawn
Application number
EP94102173A
Other languages
German (de)
English (en)
Inventor
Michael Dr. Bernheim
Dieter Walz
Werner Stechele
Erich Rössler
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.)
Pfersee Chemie GmbH
Chemische Fabrik Pfersee GmbH
Original Assignee
Pfersee Chemie GmbH
Chemische Fabrik Pfersee GmbH
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 Pfersee Chemie GmbH, Chemische Fabrik Pfersee GmbH filed Critical Pfersee Chemie GmbH
Publication of EP0616071A1 publication Critical patent/EP0616071A1/fr
Withdrawn legal-status Critical Current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
    • D06P1/64—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
    • D06P1/6426—Heterocyclic compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/35—Heterocyclic compounds
    • D06M13/355—Heterocyclic compounds having six-membered heterocyclic rings
    • D06M13/358—Triazines
    • D06M13/364—Cyanuric acid; Isocyanuric acid; Derivatives thereof

Definitions

  • the invention described below relates to a process for the treatment of fiber materials which consist of 20 to 100% by weight of cellulose fibers.
  • N-methylol compounds normally still contain residues of free formaldehyde, and they release formaldehyde to a certain extent during thermal treatment, which can lead to unpleasant odors and intolerance.
  • This disadvantage of N-methylol compounds can be reduced or avoided by using low-formaldehyde or formaldehyde-free products as crosslinkers for cellulose. Products that have etherified N-methylol groups or products that do not contain any -N-CH2-O groups are possible.
  • N, N'-dialkyl-4,5-dihydroxiimidazolidinones N, N'-dialkyl-dihydroxyethylene ureas
  • Etherification products of the last-mentioned compounds with polyhydric alcohols are also known as crosslinking agents for cellulosic materials, see for example EP-A 0 330 979.
  • the object on which the invention described below was based was to develop a process for the highly effective formaldehyde-free finishing or crease-resistant finishing of fiber materials which contain cellulose fibers or consist of cellulose fibers.
  • the process should allow the crosslinker to react with cellulose (condensation) at relatively low temperatures, i.e. Carry out temperatures of less than 150 ° C, and should lead to a higher level of crease-resistant or easy-care effect than is possible with known formaldehyde-free crosslinkers.
  • the object was achieved by a process for the treatment of fiber materials which consist of 20 to 100% by weight of cellulose fibers, which is characterized in that at least one product of the general formula (I) is applied, wherein R1, R2 and R3 each independently represent Cl or OR4 and all R4 present independently of one another for hydrogen, a metal or for stand, where n is a number from 1 to 6, preferably from 1 to 4.
  • the fiber materials can contain cellulose fibers in a mixture with other fibers, in particular polyester or polyamide, or they can consist exclusively of cellulose fibers.
  • Cellulose fibers include both natural fibers such as cotton and fibers from regenerated cellulose such as Viscose in question.
  • Suitable fiber materials which can be treated by the process according to the invention are, above all, textile fabrics or knitted fabrics.
  • the process according to the invention has a number of advantages:
  • the fiber materials to which the above-mentioned products have been applied can be dried at 80 to 130 ° C. in order to achieve good easy-care effects: temperatures up to 150 ° C. and more, such as they are required if known formaldehyde-free crosslinkers are used, do not have to be used.
  • the application of an alkaline liquor containing crosslinking agents can also be carried out by means of the wet residence process. This means that after application and a squeezing process, e.g. as part of a padding process, the fiber material, e.g. in the form of a textile fabric, protected against drying out, stored at room temperature and after a certain dwell time of e.g. Rinsed with water for 20 hours and dried. At least partial crosslinking takes place during storage in the wet state.
  • the finished and dried fiber materials often have a higher degree of whiteness than when known processes are carried out.
  • the protection against rotting of the finished fiber materials is in many cases considerably better than with known processes.
  • the method according to the invention can also advantageously be combined with other processes, such as e.g. with reactive staining in an alkaline medium or other processes to be carried out in an alkaline medium.
  • the method according to the invention also offers the advantage in many cases of less impairment of the light fastness in the case of substantive and reactive dyeings than is the case with known methods.
  • At least one product of the formula (I) given above and in claim 1 is applied to the fiber materials, which are preferably textile fabrics or knitted fabrics.
  • the fiber materials which are preferably textile fabrics or knitted fabrics.
  • mixtures of several products covered by the formula (I) can also be applied.
  • one or more products of the formula (I) can be used to apply other desired products to the fiber materials, such as, for example, agents for water-repellent, oil-repellent or flame-retardant finishing.
  • the process according to the invention can be carried out in such a way that the fiber materials are treated with aqueous solutions or dispersions which, in addition to one or more products which come under the formula (I) given above and in claim 1, also contain ammonium phosphate , Contain ammonium polyphosphate and / or a phosphate of an organic base.
  • the organic base can be, for example, guanidine, urea, dicyandiamide or guanyl urea.
  • Such product mixtures can be applied by means of a single treatment liquor, for example by padding, if these product mixtures are homogeneous mixtures.
  • a product of the formula (I) or a product mixture in the form of an alkaline aqueous solution or dispersion of this product or these products is applied to the fiber materials and the fiber materials are then dried. Drying is preferably carried out in a temperature range from 80 to 130 ° C; If necessary, however, other temperatures can also be used, for example up to 140 ° C.
  • the combination of the easy-care or crease test equipment with reactive dyeing in a single operation can be considered.
  • a reactive dye is added to the treatment liquor.
  • This preferred embodiment of the method according to the invention is particularly suitable for alkaline treatment liquors whose pH at 20 ° C. is preferably in a range from 7 to 13.
  • the solutions or dispersions to be used for the process according to the invention preferably aqueous solutions or dispersions, have a pH during storage which is not below 7.0 and not above 10 , 0, in some cases does not exceed 9.0. If higher pH values result in the production of solutions of partial hydrolyzates of cyanuric chloride which are to be used for the process according to the invention, it is advisable to subsequently adjust the solutions or dispersions to a pH value of 7 to 10 and in this form to store.
  • the setting or stabilization of the desired pH e.g. in the range of 7 to 10, e.g. by Na2CO3, K2CO3, KHCO3 or NaHCO3.
  • the amount of alkali, e.g. NaOH or KOH are added, which is required for the treatment of the fiber materials (crosslinking reaction with cellulose) and / or for the reactive dyeing.
  • the products (1.3.5-triazine derivatives) of the formula (I) include, inter alia, cyanuric chloride and its partial hydrolyzates or the cyanuric acid formed by complete hydrolysis of cyanuric chloride.
  • R4 hydrogen
  • the method according to the invention is carried out with alkaline treatment liquors.
  • the metal salts present in the alkaline aqueous medium which fall under the formula (I) and are suitable for the process according to the invention, need not be salts of monovalent metal cations.
  • R4 in formula (I) can also stand for a polyvalent metal cation.
  • two or more anions of cyanuric acid or the partial hydrolyzate of cyanuric chloride are present for each metal ion R4.
  • all R4 present in the product of the formula (I) are hydrogen or a monovalent metal or Sodium and potassium are particularly preferred as monovalent metals or metal cations.
  • the sodium or potassium salts of cyanuric acid or the partial hydrolyzates of cyanuric chloride are particularly preferred because they are water-soluble products.
  • a preferred embodiment of the process according to the invention thus consists in using water-soluble products of the formula (I); These water-soluble products are primarily Na or K salts, which are used in aqueous finishing liquors. If only these Na or K salts are used, these are preferably alkaline aqueous solutions.
  • the process according to the invention is preferably carried out using aqueous dispersions.
  • the dispersants required for dispersing such additional finishing agents in water are known to the person skilled in the art.
  • the aqueous dispersions which, in addition to at least one compound of the formula (I), contain further products also preferably have alkaline pH values in the range from pH 7 to 13.
  • polyoxyethylene derivatives of cyanuric acid or partial hydrolyzates can also be used for the process according to the invention.
  • These polyoxyethylene derivatives can be obtained by adding ethylene oxide to cyanuric acid or to partial hydrolyzates of cyanuric chloride.
  • R4 in formula (I) is The number of oxyethylene units present on average is represented by n and is between 1 and 6.
  • n has a value from 1 to 4.
  • Products are particularly preferably used for the process according to the invention in which in formula (I) R1 is Cl, R2 is Cl or OR4 and R3 is OR4, ie products obtained by hydrolysis of one or two C-Cl bonds of cyanuric chloride will.
  • R4 H
  • the fiber materials can be treated by the method according to the invention by generally known methods.
  • An application of solutions or dispersions which contain at least one product of the formula (I) by padding is very suitable.
  • This treatment is expediently carried out with an aqueous liquor which contains 1 to 12% by weight, based on the entire liquor, of one or more products of the formula (I).
  • the fiber material normally contains about 1 to 6% by weight of the product of the formula (I), based on the total weight of the finished fiber material.
  • the subsequent drying can be carried out in known devices and is preferably carried out in a temperature range from 80 to 130 ° C. A temperature gradient may be present during the drying process.
  • a reaction (crosslinking) of product of formula (I) with cellulose takes place simultaneously with the drying. This reaction is promoted by the presence of an alkaline pH.
  • crosslinking with the OH groups of cellulose is thus favored by the presence of alkaline compounds.
  • alkaline compounds of the formula (I) for example metal salts of partial hydrolyzates of cyanuric chloride (see claims 4 and 5) are already used for the process according to the invention, the addition of further alkaline compounds to the treatment liquors is recommended. Sodium hydroxide and potassium hydroxide are particularly suitable for this.
  • the process according to the invention can also be carried out in two stages.
  • first aqueous treatment liquor which contains a product of the formula (I) and a pH
  • This first aqueous treatment liquor can contain other products, such as reactive dyes.
  • This first treatment liquor can be applied by padding. After squeezing, the fiber material is dried.
  • a second aqueous treatment liquor is applied which contains the amount of alkaline compound required for crosslinking with cellulose.
  • This alkaline compound is preferably sodium hydroxide or potassium hydroxide.
  • drying is carried out, for example at 80 to 130 ° C., the crosslinking taking place.
  • the second treatment liquor can be, for example, an aqueous sodium hydroxide or potassium hydroxide solution of a relatively high concentration, for example between 30 and 60% by weight.
  • the treatment of the fiber materials with treatment liquid is preferably carried out at a pH in the range from 7 to 13 (measured at 20 ° C.).
  • the fiber materials treated by the process according to the invention are notable for good easy-care or crease-resistant properties. These properties can be determined quantitatively, for example, by determining the crease angle (crease recovery angle) or indirectly via the water retention capacity (DIN 53814). The determination of the crease angle is carried out according to DIN 53890 (1972 edition) (dry crease angle) or according to the method described in Melliand, Textile Reports 39 - 5/1958, pages 552 to 554 (wet crease angle).
  • a cotton poplin sample is dipped into a liquor containing 340 g / l of the above reaction mixture (containing about 0.2 mol of the above-mentioned Na salt) and 32 g / l of aqueous NaOH (50%) (Weight per square meter approx. 120 g), followed by padding, the liquor absorption being approx. 75%.
  • the mixture is then dried for 10 minutes at 110 ° C. and rinsed with water until the pH is around 7. Then it is dried again.
  • a cotton batiste 80 g / m2 was used instead of the poplin pattern (liquor absorption approx. 100%, other conditions as above).
  • the crease angle values can be found in the following table: Pattern dried Cotton batiste A B C. D Crease angle Chain 60 ° 76 ° 72 ° 53 ° (dry) Shot 61 ° 78 ° 77 ° 57 ° Crease angle Chain 94 ° 119 ° 125 ° 92 ° (wet) Shot 99 ° 126 ° 119 ° 93 ° Post-condensed pattern Cotton batiste A B C.
  • a higher value for the crease angle means a better effect of the crease resistant finish.
  • Another cotton batiste pattern is soaked in liquor B and subjected to a wet crosslinking process using the cold dwell process.
  • a dry crease angle of approximately 72 ° and a wet crease angle of approximately 118 ° were measured. After a hot wash, these crease angles remain unchanged.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Coloring (AREA)
EP94102173A 1993-03-13 1994-02-12 Procédé de traitement de matériaux fibreux à l'aide de dérivés de la triazine Withdrawn EP0616071A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19934308075 DE4308075A1 (de) 1993-03-13 1993-03-13 Verfahren zur Behandlung von Fasermaterialien mittels Triazinderivaten
DE4308075 1993-03-13

Publications (1)

Publication Number Publication Date
EP0616071A1 true EP0616071A1 (fr) 1994-09-21

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ID=6482754

Family Applications (1)

Application Number Title Priority Date Filing Date
EP94102173A Withdrawn EP0616071A1 (fr) 1993-03-13 1994-02-12 Procédé de traitement de matériaux fibreux à l'aide de dérivés de la triazine

Country Status (2)

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EP (1) EP0616071A1 (fr)
DE (1) DE4308075A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT2256U1 (de) * 1997-10-15 1998-07-27 Chemiefaser Lenzing Ag Verfahren zur behandlung von cellulosischen formkörpern
EP0903434A1 (fr) * 1997-09-17 1999-03-24 Ciba SC Holding AG Procédé pour le traitement de fibres cellulosiques
TR199801002A3 (tr) * 1997-06-04 1999-10-21 Ciba Specialty Chemicals Holding Inc. Selülozik lifli materyallerin çapraz-baglantisi.
TR199801842A3 (tr) * 1997-09-17 1999-10-21 Ciba Specialty Chemicals Holding Inc. Selüloz liflerin islem görme yöntemi.
WO2001023660A1 (fr) * 1999-09-30 2001-04-05 The Procter & Gamble Company Tissu de coton presentant des proprietes durables
US6252073B1 (en) 1998-08-07 2001-06-26 Degussa-Huls Ag Method of producing alkali metal salts or alkaline earth metal salts of 2,4-dichloro-6-hydroxy-s-triazine
WO2003040460A1 (fr) * 2001-11-09 2003-05-15 Degussa Ag Procede pour munir des fibres de cellulose d'une protection ignifuge
US6570011B1 (en) * 1998-09-10 2003-05-27 Degussa Ag Method for producing a stabilized aqueous alkali metal-2-hydroxy-4,6-dichloro-s-triazine solution and the use thereof
DE102007014272A1 (de) 2007-03-26 2008-10-02 Evonik Degussa Gmbh Verfahren zur Flammschutzausrüstung von Baumwolle

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3786349B1 (fr) 2019-08-29 2022-06-01 Ecoatech GmbH Traitement ignifuge de substrats absorbants

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1085492B (de) * 1958-01-24 1960-07-21 Chem Fab Gruenau Ag Verfahren zur Verbesserung des Griffes von organischem Faser- und Folienmaterial (A)
GB896814A (en) * 1959-02-18 1962-05-16 Ciba Ltd New acylating agents and process for their manufacture
DE1148222B (de) * 1958-04-10 1963-05-09 Ciba Geigy Verfahren zur Verbesserung der Eigenschaften von Cellulosefasern
US3124414A (en) * 1959-02-11 1964-03-10 Textile finishing process
EP0174794A2 (fr) * 1984-09-14 1986-03-19 Wool Development International Limited Traitement de textile

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1085492B (de) * 1958-01-24 1960-07-21 Chem Fab Gruenau Ag Verfahren zur Verbesserung des Griffes von organischem Faser- und Folienmaterial (A)
DE1148222B (de) * 1958-04-10 1963-05-09 Ciba Geigy Verfahren zur Verbesserung der Eigenschaften von Cellulosefasern
US3124414A (en) * 1959-02-11 1964-03-10 Textile finishing process
GB896814A (en) * 1959-02-18 1962-05-16 Ciba Ltd New acylating agents and process for their manufacture
EP0174794A2 (fr) * 1984-09-14 1986-03-19 Wool Development International Limited Traitement de textile

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0882836A3 (fr) * 1997-06-04 2000-11-22 Ciba SC Holding AG Procédé de réticulation de matériaux fibreux contenant de la cellulose
TR199801002A3 (tr) * 1997-06-04 1999-10-21 Ciba Specialty Chemicals Holding Inc. Selülozik lifli materyallerin çapraz-baglantisi.
TR199801842A3 (tr) * 1997-09-17 1999-10-21 Ciba Specialty Chemicals Holding Inc. Selüloz liflerin islem görme yöntemi.
US6033443A (en) * 1997-09-17 2000-03-07 Ciba Specialty Chemicals Corporation Process for treating cellulose fibres
EP0903434A1 (fr) * 1997-09-17 1999-03-24 Ciba SC Holding AG Procédé pour le traitement de fibres cellulosiques
US6241933B1 (en) 1997-10-15 2001-06-05 Lenzing Aktiengesellschaft Process for the treatment of cellulosic moulded bodies
WO1999019555A1 (fr) * 1997-10-15 1999-04-22 Lenzing Aktiengesellschaft Procede pour le traitement de corps moules cellulosiques
AT2256U1 (de) * 1997-10-15 1998-07-27 Chemiefaser Lenzing Ag Verfahren zur behandlung von cellulosischen formkörpern
US6252073B1 (en) 1998-08-07 2001-06-26 Degussa-Huls Ag Method of producing alkali metal salts or alkaline earth metal salts of 2,4-dichloro-6-hydroxy-s-triazine
US6570011B1 (en) * 1998-09-10 2003-05-27 Degussa Ag Method for producing a stabilized aqueous alkali metal-2-hydroxy-4,6-dichloro-s-triazine solution and the use thereof
WO2001023660A1 (fr) * 1999-09-30 2001-04-05 The Procter & Gamble Company Tissu de coton presentant des proprietes durables
WO2003040460A1 (fr) * 2001-11-09 2003-05-15 Degussa Ag Procede pour munir des fibres de cellulose d'une protection ignifuge
JP2005508458A (ja) * 2001-11-09 2005-03-31 デグサ アクチエンゲゼルシャフト セルロース繊維を防炎加工する方法
US8177859B2 (en) 2001-11-09 2012-05-15 Evonik Degussa Gmbh Method of flameproofing cellulose fibers
DE102007014272A1 (de) 2007-03-26 2008-10-02 Evonik Degussa Gmbh Verfahren zur Flammschutzausrüstung von Baumwolle

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