EP1630280A1 - Procédé pour le traitement de produits textiles - Google Patents

Procédé pour le traitement de produits textiles Download PDF

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Publication number
EP1630280A1
EP1630280A1 EP04020579A EP04020579A EP1630280A1 EP 1630280 A1 EP1630280 A1 EP 1630280A1 EP 04020579 A EP04020579 A EP 04020579A EP 04020579 A EP04020579 A EP 04020579A EP 1630280 A1 EP1630280 A1 EP 1630280A1
Authority
EP
European Patent Office
Prior art keywords
solution
radical
silicon compounds
ammonia
silicon compound
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Withdrawn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
EP04020579A
Other languages
German (de)
English (en)
Inventor
Jürgen Dr. Ellmann
Rule Niederstadt
Harald Dr. Chrobaczek
Ernst Springer
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.)
Huntsman Textile Effects Germany GmbH
Original Assignee
Huntsman Textile Effects Germany GmbH
Ciba Spezialitaetenchemie 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 Huntsman Textile Effects Germany GmbH, Ciba Spezialitaetenchemie Pfersee GmbH filed Critical Huntsman Textile Effects Germany GmbH
Priority to EP04020579A priority Critical patent/EP1630280A1/fr
Priority to PCT/EP2005/008552 priority patent/WO2006024364A1/fr
Priority to US11/659,528 priority patent/US20080115290A1/en
Priority to CNA2005800289843A priority patent/CN101010457A/zh
Priority to EP05768410A priority patent/EP1792002A1/fr
Priority to KR1020077005013A priority patent/KR20070047817A/ko
Publication of EP1630280A1 publication Critical patent/EP1630280A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/50Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
    • D06M13/51Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond
    • D06M13/513Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond with at least one carbon-silicon bond
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M11/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/58Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with nitrogen or compounds thereof, e.g. with nitrides
    • D06M11/59Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with nitrogen or compounds thereof, e.g. with nitrides with ammonia; with complexes of organic amines with inorganic substances
    • D06M11/61Liquid ammonia
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2101/00Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/02Natural fibres, other than mineral fibres
    • D06M2101/04Vegetal fibres
    • D06M2101/06Vegetal fibres cellulosic
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/20Treatment influencing the crease behaviour, the wrinkle resistance, the crease recovery or the ironing ease

Definitions

  • the invention relates to a process for the treatment of textile fabrics, wherein a specific silicon compound or a mixture of silicon compounds is applied to the fabrics and then the fabrics are dried.
  • cellulose crosslinkers those skilled in the art, inter alia N-methylol compounds are known. Although these lead to good crosslinking results, however, can have a disturbing effect that they contain formaldehyde as a by-product or release at elevated temperature or during storage. Alternative products were sought as crosslinkers which neither contain nor release formaldehyde during processing. It was found that crosslinking of cellulose fibers can also be achieved by treatment with silanes. Methods in which silanes are used as cellulose crosslinkers are known. Thus, US Pat. No. 3,055,774, EP-A 563 961 and EP-A 401 668 describe the treatment of cellulose or cellulose derivatives with functional silanes. In all of these processes, the silane is used in the form of an aqueous composition.
  • the object on which the present invention was based was to develop a process by means of which a highly effective crosslinking of textile fabrics containing considerable amounts of cellulose fibers can be carried out. Further, the process should allow to use as crosslinking agents also those silicon compounds which are unstable in aqueous systems or which do not have optimal reactivity.
  • the object has been achieved by a process for the treatment of textile fabrics, which consist of 70 to 100% by weight of cellulose fibers, with a solution of a silicon compound or a mixture of silicon compounds in liquid ammonia, which solution is applied to the textile fabric and then the fabric is dried, wherein at least one of the silicon compounds used corresponds to one of the formulas (I) to (IV).
  • textile fabrics are treated which consist of 70 to 100% by weight of cellulose fibers.
  • Textile fabrics include wovens, knits and fleeces (nonwovens). Preference is given to tissue.
  • the textile fabrics contain from 70 to 100% by weight of cellulose fibers. If it is not 100% cellulosic material, the remainder may be synthetic fibers such as polyester or polyamide.
  • the cellulose fibers may consist of natural cellulose such as cotton or regenerated cellulose.
  • the textile fabrics treated by the process according to the invention can be further processed, inter alia, into articles of clothing.
  • said textile fabrics are treated with a solution of a silicon compound of the type described below in liquid ammonia.
  • a silicon compound of the type described below in liquid ammonia.
  • a mixture of silicon compounds may also be used.
  • At least one of the silicon compounds used here corresponds to one of the formulas (I) to (IV) explained below.
  • all silicon compounds used fall under one of these formulas, so it is preferred that no silicon compounds are present which do not correspond to the formulas (I) to (IV), but optionally in the solution in liquid ammonia additionally amino-functional polysiloxanes or other softening agent present be.
  • all silicon compounds or other softening agents used must be readily soluble in liquid ammonia.
  • the application of the ammoniacal solution to the textile fabrics can be carried out by methods known in the textile industry.
  • An application by means of a bath, eg according to a padder application, in which the fabrics are immersed in a solution of the desired silicon compound in liquid ammonia, is very suitable.
  • the residence time of the textile fabric in the ammoniacal solution is normally about 20 seconds to 20 minutes, but may be longer. It is then squeezed in a known manner.
  • the solution of the corresponding silicon compound or the mixture of silicon compounds preferably has a temperature in the range of -60 ° C to -40 ° C when applied to the sheet. This applies regardless of which method is used.
  • the ammonia solution normally contains about 0.01 to 3, preferably 0.1 to 0.7 parts by weight of silicon compound per 100 parts by weight of ammonia. These figures are based on the total amount of all silicon compounds used, which fall under one of the formulas (I) to (IV).
  • the solution of the silicon compound or the silicon compounds in liquid ammonia additionally contains a catalyst.
  • Suitable catalysts cause an increased degree of crosslinking and thus better effects with regard to creasing behavior of the finished textiles and / or its permanence.
  • Well suited as catalysts are sterically hindered amines such as e.g. Diaza-bicyclo [2.2.2] octane (DABCO) or 4-dimethylaminopyridine (4-DMAP).
  • the amount of catalyst added is preferably 1.0 to 3% by weight, based on the total amount of silicon compounds of formulas (I) to (IV) present in the ammoniacal solution.
  • the textile fabrics After application of the ammoniacal solution, the textile fabrics must be dried. This can be done with known drying equipment. The drying is normally carried out at a temperature in the range of 60 ° C to 180 ° C, preferably from 80 ° C to 150 ° C and is carried out until ammonia, water and optionally formed alcohol are removed. Normally this requires a drying time of about 5 to 30 minutes. Namely, in the case of using silicon compounds in which OH or OR groups are bonded to silicon atoms, water or alcohol is formed in the crosslinking reaction with OH groups of the cellulose. In many cases, it is advantageous if a Sanfor process is carried out on the textile fabrics before drying. This is understood to mean a mechanical shrinkage of textile goods, as described, for example, in K.
  • condensation is still carried out after the textile fabric has dried, in particular when the drying temperature is below 130 ° C.
  • This is a higher temperature treatment, e.g. in the range of 130 ° C to 180 ° C, preferably 140 ° C to 170 ° C, for a time of 2 to 10 minutes.
  • the condensation can increase the number of bonds that form between cellulose and the reactive silicon compounds.
  • At least one of the silicon compounds used for the process according to the invention must correspond to one of the formulas (I) to (IV).
  • All of these silicon compounds contain 2 or more reactive groups which can react with OH groups of the cellulose, optionally at elevated temperature.
  • the result of this reaction is a cross-linking of cellulose chains, which results in an improvement of the creasing behavior.
  • Silicon compounds or silanes of the formulas (I) to (IV) and their preparation are known from the prior art, for example from the documents mentioned at the outset and from EP-A 1 199 339 or by methods known to the person skilled in the art, for example by reaction of halosilanes with alcohols. Furthermore, silicon compounds of the formulas (I) to (IV) are available on the market, for example from Wacker, DE.
  • a measuring device for determining the wet crease angle (also called “crease recovery angle wet") is described.
  • This device can be used to determine the creasing behavior of textile fabrics.
  • the values for the crease recovery angle wet stated below in the exemplary embodiments 1a) to 1d) are based on determinations according to this Melliand citation. For this determination, the samples were prepared as follows: Tissue samples of 2 cm ⁇ 1 cm were placed in an aqueous solution containing 1 g / L of wetting agent (sodium salt of an alkylnaphthalenesulfonate). After 5 minutes, the samples were removed, placed on a plastic splint, folded and weighed for 3 minutes with a 500 g weight loaded. Then it was relieved for 3 minutes and then the crease recovery angle was measured.
  • wetting agent sodium salt of an alkylnaphthalenesulfonate
  • Table 1 0.1 ml of ⁇ -glycidoxypropyltriethoxysilane in 25 ml of ammonia Residence time in ammonia catalyst Ammonia temperature [° C] Drying (T) and optionally condensation conditions (K) Crease recovery angle wet [°] 30 s - -40 10 min 110 ° C + 5 min 150 ° C (T + K) 71 5 min DABCO -40 10 min 110 ° C (T) 75 5 min DABCO -40 10 min 110 ° C + 5 min 150 ° C (T + K) 82
  • Table 2 0.1 ml of 1,2-bis (methoxydimethylsilyl) ethane in 25 ml of ammonia Residence time in ammonia catalyst Ammonia temperature [° C] Drying (T) and optionally condensation conditions (K) Crease recovery angle wet [°] 30 s - -40 10 min 110 ° C (T) 71 30 s - -40 10 min 110 ° C + 5 min 150 ° C (T + K) 80 1 min - -40 10 min 110 ° C (T) 73 1 min - -40 10 min 110 ° C + 5 min 150 ° C (T + K) 84 5 min DABCO -60 10 min 110 ° C (T) 75 5 min DABCO -60 10 min 110 ° C + 5 min 150 ° C (T + K) 82 5 min DABCO -40 10 min 110 ° C (T) 72 5 min DABCO -40 10 min 110 ° C + 5 min 150 ° C (T + K) 80
  • Table 3 0.1 ml of ⁇ -glycidoxypropylmethyldiethoxysilane in 25 ml of ammonia Residence time in ammonia [min] catalyst Ammonia temperature [° C] Drying (T) and optionally condensation conditions (K) Crease recovery angle wet [°] 5 DABCO -40 10 min 110 ° C + 5 min 150 ° C (T + K) 76
  • Table 4 0.1 ml of triethoxy (2,4,4-trimethylpentyl) silane in 25 ml of ammonia Residence time in ammonia Ammonia temperature [° C] Drying conditions (T) Crease recovery angle wet [°] 10 s -40 10 min 110 ° C (T) 72 1 min -40 10 min 110 ° C (T) 78

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
EP04020579A 2004-08-31 2004-08-31 Procédé pour le traitement de produits textiles Withdrawn EP1630280A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
EP04020579A EP1630280A1 (fr) 2004-08-31 2004-08-31 Procédé pour le traitement de produits textiles
PCT/EP2005/008552 WO2006024364A1 (fr) 2004-08-31 2005-08-06 Traitement de tissus textiles
US11/659,528 US20080115290A1 (en) 2004-08-31 2005-08-06 Treatment Of Textile Fabrics
CNA2005800289843A CN101010457A (zh) 2004-08-31 2005-08-06 织物处理
EP05768410A EP1792002A1 (fr) 2004-08-31 2005-08-06 Procédé pour le traitement de produits textiles
KR1020077005013A KR20070047817A (ko) 2004-08-31 2005-08-06 섬유 직물의 처리

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP04020579A EP1630280A1 (fr) 2004-08-31 2004-08-31 Procédé pour le traitement de produits textiles

Publications (1)

Publication Number Publication Date
EP1630280A1 true EP1630280A1 (fr) 2006-03-01

Family

ID=34926356

Family Applications (2)

Application Number Title Priority Date Filing Date
EP04020579A Withdrawn EP1630280A1 (fr) 2004-08-31 2004-08-31 Procédé pour le traitement de produits textiles
EP05768410A Withdrawn EP1792002A1 (fr) 2004-08-31 2005-08-06 Procédé pour le traitement de produits textiles

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP05768410A Withdrawn EP1792002A1 (fr) 2004-08-31 2005-08-06 Procédé pour le traitement de produits textiles

Country Status (5)

Country Link
US (1) US20080115290A1 (fr)
EP (2) EP1630280A1 (fr)
KR (1) KR20070047817A (fr)
CN (1) CN101010457A (fr)
WO (1) WO2006024364A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015131965A1 (fr) * 2014-03-04 2015-09-11 Henkel Ag & Co. Kgaa Matière première et son utilisation pour la réduction des plis dans les textiles

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11098444B2 (en) 2016-01-07 2021-08-24 Tommie Copper Ip, Inc. Cotton performance products and methods of their manufacture
CN109944062B (zh) * 2019-03-05 2021-04-27 武汉纺织大学 一种棉织物的液氨溶胀与原位可控免烫的整理方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3055774A (en) * 1960-09-01 1962-09-25 Dow Corning Method of rendering cellulose fabrics water-repellent and crease-resistant
DE3104531A1 (de) * 1980-02-28 1981-12-03 Chemiefaser Lenzing AG, 4860 Lenzing, Oberösterreich Verfahren zur herstellung neuer o-trimethylsilyl-cellulosen
DE19511112A1 (de) * 1995-03-25 1996-09-26 Pfersee Chem Fab Verfahren zur Behandlung von Cellulose enthaltenden Geweben
EP0900874A2 (fr) * 1997-09-08 1999-03-10 Nisshinbo Industries Inc. Procédé de traitement de matériaux textiles contenant des fibres de cellulose

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA906995A (en) * 1972-03-09 1972-08-08 S. Troope Walter Method for mixing liquid ammonia with conventional dyes and other conventional fabric-finishing materials
US4345908A (en) * 1979-11-28 1982-08-24 Joshua L. Baily & Co., Inc. Stretchable woven cellulosic fabric and process for making same
CA1189665A (fr) * 1981-09-24 1985-07-02 Asahi Kasei Kogyo Kabushiki Kaisha Methode de modification de la fibre de cellulose regeneree
US4992538A (en) * 1989-06-05 1991-02-12 Aqualon Company Silated polysaccharides
US5071978A (en) * 1989-06-05 1991-12-10 Aqualon Company Silated polysaccharide process
US5032682A (en) * 1989-06-05 1991-07-16 Aqualon Company Silated polysaccharides
DE4211256A1 (de) * 1992-04-03 1993-10-07 Wacker Chemie Gmbh Vernetzbare Zusammensetzung auf Aminosiliconbasis
FR2770232B1 (fr) * 1997-10-27 2000-01-14 Rhodia Ag Rhone Poulenc Procede de preparation d'une fibre ou d'un fil de cellulose regeneree

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3055774A (en) * 1960-09-01 1962-09-25 Dow Corning Method of rendering cellulose fabrics water-repellent and crease-resistant
DE3104531A1 (de) * 1980-02-28 1981-12-03 Chemiefaser Lenzing AG, 4860 Lenzing, Oberösterreich Verfahren zur herstellung neuer o-trimethylsilyl-cellulosen
DE19511112A1 (de) * 1995-03-25 1996-09-26 Pfersee Chem Fab Verfahren zur Behandlung von Cellulose enthaltenden Geweben
EP0900874A2 (fr) * 1997-09-08 1999-03-10 Nisshinbo Industries Inc. Procédé de traitement de matériaux textiles contenant des fibres de cellulose

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015131965A1 (fr) * 2014-03-04 2015-09-11 Henkel Ag & Co. Kgaa Matière première et son utilisation pour la réduction des plis dans les textiles

Also Published As

Publication number Publication date
KR20070047817A (ko) 2007-05-07
US20080115290A1 (en) 2008-05-22
WO2006024364A1 (fr) 2006-03-09
CN101010457A (zh) 2007-08-01
EP1792002A1 (fr) 2007-06-06

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