EP1463858B1 - Method for treating cellulosic moulded bodies - Google Patents

Method for treating cellulosic moulded bodies Download PDF

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Publication number
EP1463858B1
EP1463858B1 EP02796479A EP02796479A EP1463858B1 EP 1463858 B1 EP1463858 B1 EP 1463858B1 EP 02796479 A EP02796479 A EP 02796479A EP 02796479 A EP02796479 A EP 02796479A EP 1463858 B1 EP1463858 B1 EP 1463858B1
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EP
European Patent Office
Prior art keywords
cyclodextrin
fibers
process according
moulded bodies
hydroxy
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Expired - Lifetime
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EP02796479A
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German (de)
French (fr)
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EP1463858A2 (en
Inventor
Christian Rohrer
Werner Richardt
Evelyn Schobesberger
Gerhard Reiter
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Lenzing AG
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Lenzing AG
Chemiefaser Lenzing AG
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Publication of EP1463858A2 publication Critical patent/EP1463858A2/en
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Classifications

    • 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
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
    • D06M15/03—Polysaccharides or derivatives thereof
    • 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
    • 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
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/02—Natural fibres, other than mineral fibres
    • D06M2101/04—Vegetal fibres
    • D06M2101/06—Vegetal fibres cellulosic

Definitions

  • the invention relates to a process for the treatment of cellulosic molded articles, which are prepared from a solution of cellulose in an aqueous tertiary amine oxide, in particular fibers and structures containing these fibers, in which process the shaped bodies are brought into contact with a textile auxiliary in order to Give moldings improved properties.
  • shaped body includes sponges in particular.
  • the solvent used is a tertiary amine oxide, in particular N-methylmorpholine-N-oxide (NMMO).
  • NMMO N-methylmorpholine-N-oxide
  • the WO 99/19555 describes a process for treating solvent-spun fibers in which the fibers are contacted with 2,4-dichloro-6-hydroxy-1,3,5-triazine or with a salt thereof.
  • the fibers thus produced are characterized by a better resistance to fibrillation.
  • the WO 01/48025 describes cyclodextrins which are covalently bound to a polysaccharide by means of a crosslinking agent.
  • cellulosic molded articles prepared from a solution of the cellulose in an aqueous tertiary amine oxide can be treated with a textile auxiliary comprising a cyclodextrin and / or a cyclodextrin derivative to give products having improved properties.
  • the moldings are preferably fibers in never-dried state.
  • the fibers can be treated in a never-dried state in a post-treatment stage of a continuous processing plant.
  • cyclodextrins may include drugs that are then released, for example, over a longer period of time.
  • the treatment with the textile auxiliaries is preferably carried out in an alkaline medium.
  • the textile auxiliary additionally comprises a crosslinking agent.
  • a crosslinking agent particularly preference is given to using 2,4-dichloro-6-hydroxy-1,3,5-triazine or a salt thereof as crosslinking agent.
  • the textile auxiliary comprises 2-chloro-4-hydroxy-1,3,5-triazinyl-cyclodextrin (MCT-CD) or a salt thereof.
  • the invention also relates to a solvent-spun cellulosic fiber obtainable by the process according to the invention and to fiber structures which contain these fibers.
  • the fibers were mixed at a liquor ratio of 1:10 with a solution containing 20 g / l sodium salt of 2,4-dichloro-6-hydroxy-1,3,5-triazine, 16 g / l NaOH and 100 g / l of a cyclodextrin ( CAVAMAX W7, manufacturer Wacker-Chemie) for 5 minutes at room temperature impregnated.
  • the fibers were then squeezed to a moisture content of 100% -110% by means of a squeezer and heat treated for 5 minutes with saturated steam (100%) at 100 ° C, washed and dried.
  • the content of active cyclodextrin in the fibers thus produced was determined photometrically (552 nm) on the basis of the decolorization of a phenolphthalein solution and was 2.33% by weight.
  • the degree of fibrillation was determined by wet scrub resistance (test method according to WO 99/19555 ) of the individual fibers. According to this test method, a value of 210 revolutions results on average for the sample treated according to the invention. An untreated fiber, in comparison, exhibits a wet rub of only 40-60 turns.
  • Example 2 The procedure was as in Example 1, wherein the treatment solution 20 g / l sodium salt of 2,4-dichloro-6-hydroxy-1,3,5-triazine, 16 g / l NaOH, 30 g / l of soda and 50 g / l of a Cyclodextrins (CAVAMAX W7, manufacturer Fa. Wacker-Chemie) contained.
  • CAVAMAX W7 Cyclodextrins
  • the content of active cyclodextrin in the fibers thus obtained was 1.65 wt.%, The wet abrasion value was 470 revolutions.
  • Example 2 The procedure was as in Example 1, the treatment solution containing 30 g / l of sodium carbonate and 100 g / l of 2-chloro-4-hydroxy-1,3,5-triazinylcyclodextrin (MCT-CD; CAVASOL W7 MCT, manufacturer Wacker-Chemie). Chemistry).
  • the content of active MCT-CD in the fibers thus obtained was 1.89 wt%.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Artificial Filaments (AREA)

Description

Die Erfindung betrifft ein Verfahren zur Behandlung von cellulosischen Formkörpern, die aus einer Lösung der Cellulose in einem wäßrigen tertiären Aminoxid hergestellt werden, insbesondere Fasern und Gebilde, welche diese Fasern enthalten, bei welchem Verfahren die Formkörper mit einem Textilhilfsmittel in Kontakt gebracht werden, um den Formkörpern verbesserte Eigenschaften zu verleihen.The invention relates to a process for the treatment of cellulosic molded articles, which are prepared from a solution of cellulose in an aqueous tertiary amine oxide, in particular fibers and structures containing these fibers, in which process the shaped bodies are brought into contact with a textile auxiliary in order to Give moldings improved properties.

Für die Zweck der vorliegenden Erfindung umfaßt der Begriff "Formkörper" insbesondere auch Schwämme.For the purposes of the present invention, the term "shaped body" includes sponges in particular.

Als Alternative zum Viskoseverfahren wurden in den letzten Jahren eine Reihe von Verfahren beschrieben, bei denen Cellulose ohne Bildung eines Derivats in einem organischen Lösungsmittel, einer Kombination eines organischen Lösungsmittels mit einem anorganischen Salz oder in wäßriger Salzlösung gelöst wird. Cellulosefasern, die aus solchen Lösungen hergestellt werden, heißen "lösungsmittelgesponnene" Fasern und erhielten von der BISFA (The International Büreau for the Standardisation of man made Fibres) den Gattungsnamen Lyocell. Als Lyocell wird von der BISFA eine Cellulosefaser definiert, die durch ein Spinnverfahren aus einem organischen Lösungsmittel erhalten wird. Unter "organisches Lösungsmittel" wird von der BISFA ein Gemisch aus einer organischen Chemikalie und Wasser verstanden. "Lösungsmittelspinnen" soll Auflösen und Spinnen ohne Derivatisierung bedeuten.As an alternative to the viscose process, a number of processes have been described in recent years in which cellulose is dissolved without formation of a derivative in an organic solvent, a combination of an organic solvent with an inorganic salt or in an aqueous salt solution. Cellulosic fibers made from such solutions are called "solvent spun" fibers and have been given the generic name Lyocell by BISFA (The International Bureau for the Standardization of Man Made Fibers). As lyocell, BISFA defines a cellulose fiber obtained by an organic solvent spinning method. By "organic solvent" is meant by the BISFA a mixture of an organic chemical and water. "Solvent spinning" is intended to mean dissolution and spinning without derivatization.

Bis heute hat sich jedoch nur ein einziges Verfahren zur Herstellung einer lösungsmittelgesponnenen Cellulosefaser bis zur industriellen Realisierung durchgesetzt. Bei diesem Verfahren wird als Lösungsmittel ein tertiäres Aminoxid, insbesondere N-Methylmorpholin-N-oxid (NMMO), verwendet. Ein solches Verfahren ist z.B. in der US-A 4,246,221 beschrieben und liefert Fasern, die sich durch eine hohe Festigkeit, einen hohen Naßmodul und durch eine hohe Schlingenfestigkeit auszeichnen.To date, however, only a single method for producing a solvent-spun cellulose fiber has prevailed to industrial realization. In this process, the solvent used is a tertiary amine oxide, in particular N-methylmorpholine-N-oxide (NMMO). Such a method is eg in the US-A 4,246,221 describes and supplies fibers that are characterized by a high strength, a high wet modulus and a high loop strength.

Die WO 99/19555 beschreibt ein Verfahren zur Behandlung lösungsmittelgesponnener Fasern, bei welchem die Fasern mit 2,4-dichlor-6-hydroxy-1.3.5-triazin bzw. mit einem Salz davon in Kontakt gebracht werden. Die so hergestellten Fasern zeichnen sich durch eine bessere Beständigkeit gegenüber Fibrillation aus.The WO 99/19555 describes a process for treating solvent-spun fibers in which the fibers are contacted with 2,4-dichloro-6-hydroxy-1,3,5-triazine or with a salt thereof. The fibers thus produced are characterized by a better resistance to fibrillation.

Aus der US 5,728,823 sind Cyclodextrinderivate, unter anderem das Natriumsalz des 2-chloro-4-hydroxy-1.3.5-triazinylcyclodextrins bekannt. Die US 5,728,823 beschreibt weiters Membranen, Folien, Textilien oder Leder, an welche ein Cyclodextrinderivat gebunden ist. Mit Cyclodextrinderivaten behandelte Textilien eignen sich z.B. zur Absorption unangenehmer Gerüche.From the US 5,728,823 Cyclodextrin derivatives, including the sodium salt of 2-chloro-4-hydroxy-1,3,5-triazinylcyclodextrins known. The US 5,728,823 describes further Membranes, films, textiles or leather, to which a cyclodextrin derivative is bound. Textiles treated with cyclodextrin derivatives are suitable, for example, for absorbing unpleasant odors.

Die WO 01/48025 beschreibt Cyclodextrine, welche mittels eines Vernetzungsmittels kovalent an ein Polysaccharid gebunden sind.The WO 01/48025 describes cyclodextrins which are covalently bound to a polysaccharide by means of a crosslinking agent.

Es wurde nun gefunden, daß man cellulosische Formkörper, die aus einer Lösung der Cellulose in einem wäßrigen tertiären Aminoxid hergestellt werden, mit einem Textilhilfsmittel, welches ein Cyclodextrin und/oder ein Cyclodextrinderivat umfaßt, behandeln kann, wodurch Produkte mit verbesserten Eigenschaften entstehen.It has now been found that cellulosic molded articles prepared from a solution of the cellulose in an aqueous tertiary amine oxide can be treated with a textile auxiliary comprising a cyclodextrin and / or a cyclodextrin derivative to give products having improved properties.

Bevorzugt handelt es sich bei den Formkörpern um Fasern in niemals getrocknetem Zustand. Die Fasern können in niemals getrocknetem Zustand in einer Nachbehandlungsstufe einer kontinuierlich arbeitenden Produktionsanlage behandelt werden.The moldings are preferably fibers in never-dried state. The fibers can be treated in a never-dried state in a post-treatment stage of a continuous processing plant.

Es ist bekannt, daß Cyclodextrine Wirkstoffe einschließen können, die dann beispielsweise über einen längeren Zeitraum freigesetzt werden. Im erfindungsgemäßen Verfahren ist es möglich, die im Zuge des kontinuierlichen Produktionsverfahrens mit einem Cyclodextrin bzw. einem Cyclodextrinderivat behandelte Faser gleichzeitig und/oder nachfolgend mit einem solchen Wirkstoff zu beladen.It is known that cyclodextrins may include drugs that are then released, for example, over a longer period of time. In the process according to the invention, it is possible to load the fiber treated with a cyclodextrin or a cyclodextrin derivative in the course of the continuous production process simultaneously and / or subsequently with such an active substance.

Die Behandlung mit dem Textilhilfsmittel erfolgt bevorzugt in alkalischem Milieu.The treatment with the textile auxiliaries is preferably carried out in an alkaline medium.

Weiters bevorzugt umfaßt das Textilhilfsmittel zusätzlich ein Vernetzungsmittel. Insbesondere bevorzugt wird als Vernetzungsmittel 2,4-dichlor-6-hydroxy-1.3.5-triazin bzw. ein Salz davon eingesetzt.Further preferably, the textile auxiliary additionally comprises a crosslinking agent. Particular preference is given to using 2,4-dichloro-6-hydroxy-1,3,5-triazine or a salt thereof as crosslinking agent.

Im Stand der Technik gemäß US 5,728,823 muß zunächst aufwendig ein Cyclodextrinderivat, z.B. das Natriumsalz des 2-chlor-4-hydroxy-1.3.5-triazinylcyclodextrins, hergestellt werden, um dieses Derivat anschließend auf das zu behandelnde Material aufzubringen.In the prior art according to US 5,728,823 must first consuming a cyclodextrin derivative, for example, the sodium salt of 2-chloro-4-hydroxy-1.3.5-triazinylcyclodextrins, are prepared to subsequently apply this derivative to the material to be treated.

Es hat sich nun gezeigt, daß man den zu behandelnden Fasern das Cyclodextrin und ein Vernetzungsmittel, insbesondere das 2,4-dichlor-6-hydroxy-1.3.5-triazin, ohne zuvor eine Verbindung aus diesen beiden Substanzen herstellen zu müssen, zugeben kann und zu guten Resultaten gelangt.It has now been found that it is possible to add to the fibers to be treated the cyclodextrin and a crosslinking agent, in particular 2,4-dichloro-6-hydroxy-1,3,5-triazine, without first having to prepare a compound of these two substances and get good results.

In einer weiteren Ausführungsform des erfindungsgemäßen Verfahrens umfaßt das Textilhilfsmittel 2-chlor-4-hydroxy-1.3.5-triazinyl-cyclodextrin (MCT-CD) bzw. ein Salz davon.In a further embodiment of the process according to the invention, the textile auxiliary comprises 2-chloro-4-hydroxy-1,3,5-triazinyl-cyclodextrin (MCT-CD) or a salt thereof.

Die Erfindung betrifft auch eine lösungsmittelgesponnene cellulosische Faser, die nach dem erfindungsgemäßen Verfahren erhältlich ist, sowie Fasergebilde, welche diese Fasern enthalten.The invention also relates to a solvent-spun cellulosic fiber obtainable by the process according to the invention and to fiber structures which contain these fibers.

Beispiel 1:Example 1:

Gemäß dem in der WO 93/19230 beschriebenen Verfahren hergestellte lösungsmittelgesponnene Fasern mit einem Titer von 1,3 dtex wurden in niemals getrocknetem Zustand wie folgt behandelt:According to the in the WO 93/19230 Solvent-spun fibers having a linear density of 1.3 dtex and prepared in the described method were treated as never before dried as follows:

Die Fasern wurden bei einem Flottenverhältnis von 1:10 mit einer Lösung, enthaltend 20 g/l Natriumsalz des 2,4-dichlor-6-hydroxy-1.3.5-triazins, 16 g/l NaOH und 100 g/l eines Cyclodextrins (CAVAMAX W7, Hersteller Fa. Wacker-Chemie) 5 Minuten bei Raumtemperatur imprägniert. Anschließend wurden die Fasern mittels eines Quetschwerkes auf einen Feuchtigkeitsgehalt von 100%-110% abgequetscht und 5 Minuten mit Sattdampf (100%) bei 100°C wärmebehandelt, ausgewaschen und getrocknet.The fibers were mixed at a liquor ratio of 1:10 with a solution containing 20 g / l sodium salt of 2,4-dichloro-6-hydroxy-1,3,5-triazine, 16 g / l NaOH and 100 g / l of a cyclodextrin ( CAVAMAX W7, manufacturer Wacker-Chemie) for 5 minutes at room temperature impregnated. The fibers were then squeezed to a moisture content of 100% -110% by means of a squeezer and heat treated for 5 minutes with saturated steam (100%) at 100 ° C, washed and dried.

Der Gehalt an aktivem Cyclodextrin in den so hergestellten Fasern wurde anhand der Entfärbung einer Phenolphthalein-Lösung photometrisch (552 nm) ermittelt und betrug 2,33 Gew.%.The content of active cyclodextrin in the fibers thus produced was determined photometrically (552 nm) on the basis of the decolorization of a phenolphthalein solution and was 2.33% by weight.

An den Fasern wurde der Fibrillationsgrad anhand der Naßscheuerbeständigkeit (Prüfmethode gemäß WO 99/19555 ) der Einzelfasern bestimmt. Nach dieser Testmethode ergibt sich für die erfindungsgemäß behandelte Probe im Mittel ein Wert von 210 Umdrehungen. Eine unbehandelte Faser zeigt im Vergleich dazu einen Naßscheuerwert von lediglich 40-60 Umdrehungen.On the fibers, the degree of fibrillation was determined by wet scrub resistance (test method according to WO 99/19555 ) of the individual fibers. According to this test method, a value of 210 revolutions results on average for the sample treated according to the invention. An untreated fiber, in comparison, exhibits a wet rub of only 40-60 turns.

Beispiel 2:Example 2:

Es wurde wie im Beispiel 1 vorgegangen, wobei die Behandlungslösung 20 g/l Natriumsalz des 2,4-dichlor-6-hydroxy-1.3.5-triazins, 16 g/l NaOH, 30 g/l Soda und 50 g/l eines Cyclodextrins (CAVAMAX W7, Hersteller Fa. Wacker-Chemie) enthielt.The procedure was as in Example 1, wherein the treatment solution 20 g / l sodium salt of 2,4-dichloro-6-hydroxy-1,3,5-triazine, 16 g / l NaOH, 30 g / l of soda and 50 g / l of a Cyclodextrins (CAVAMAX W7, manufacturer Fa. Wacker-Chemie) contained.

Der Gehalt an aktivem Cyclodextrin in den so erhaltenen Fasern betrug 1,65 Gew.%, der Naßscheuerwert lag bei 470 Umdrehungen.The content of active cyclodextrin in the fibers thus obtained was 1.65 wt.%, The wet abrasion value was 470 revolutions.

Beispiel 3:Example 3:

Es wurde wie im Beispiel 1 vorgegangen, wobei die Behandlungslösung 30 g/l Soda und 100 g/l 2-Chlor-4-hydroxy-1.3.5-triazinyl-cyclodextrin (MCT-CD; CAVASOL W7 MCT, Hersteller Fa. Wacker-Chemie) enthielt.The procedure was as in Example 1, the treatment solution containing 30 g / l of sodium carbonate and 100 g / l of 2-chloro-4-hydroxy-1,3,5-triazinylcyclodextrin (MCT-CD; CAVASOL W7 MCT, manufacturer Wacker-Chemie). Chemistry).

Der Gehalt an aktivem MCT-CD in den so erhaltenen Fasern betrug 1,89 Gew.%.The content of active MCT-CD in the fibers thus obtained was 1.89 wt%.

Claims (7)

  1. A process for the treatment of cellulosic moulded bodies produced from a solution of cellulose in an aqueous tertiary amine oxide, in particular fibres, wherein the moulded bodies are contacted with a textile auxiliary agent, characterized in that the textile auxiliary agent comprises a cyclodextrin and/or a cyclodextrin derivative.
  2. A process according to claim 1, characterized in that the moulded bodies are fibres in the never-dried state.
  3. A process according to claim 1 or 2, characterized in that the textile auxiliary agent additionally comprises a cross-linking agent.
  4. A process according to claim 3, characterized in that 2,4-dichloro-6-hydroxy-1.3.5-triazine or a salt thereof, respectively, is used as the cross-linking agent.
  5. A process according to claim 1 or 2, characterized in that the textile auxiliary agent comprises 2-chloro-4-hydroxy-1.3.5-triazinyl-cyclodextrin or a salt thereof, respectively.
  6. A cellulosic moulded body, in particular fibres, obtainable according to the process according to any of claims 1 to 5.
  7. A fibre assembly, containing solvent-spun, cellulosic fibres according to claim 6.
EP02796479A 2001-12-20 2002-12-19 Method for treating cellulosic moulded bodies Expired - Lifetime EP1463858B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
AT0201201A AT413988B (en) 2001-12-20 2001-12-20 METHOD FOR THE TREATMENT OF CELLULOSIC FORM BODIES
AT20122001 2001-12-20
PCT/AT2002/000362 WO2003054283A2 (en) 2001-12-20 2002-12-19 Method for treating cellulosic moulded bodies

Publications (2)

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EP1463858A2 EP1463858A2 (en) 2004-10-06
EP1463858B1 true EP1463858B1 (en) 2010-10-06

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EP (1) EP1463858B1 (en)
JP (1) JP2005535790A (en)
KR (1) KR100910989B1 (en)
CN (1) CN1311123C (en)
AT (2) AT413988B (en)
AU (1) AU2002361375A1 (en)
DE (1) DE50214703D1 (en)
TW (1) TWI273148B (en)
WO (1) WO2003054283A2 (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100398741C (en) * 2006-09-21 2008-07-02 浙江理工大学 Production of cyclodextrin-phthalocyanine double analog enzyme functional fibre
CN100415980C (en) * 2006-09-21 2008-09-03 浙江理工大学 Production of cyclodextrin-phthalocyanine double analog enzyme functional fibre
CN100392173C (en) * 2006-09-21 2008-06-04 浙江理工大学 Preparation method of cyclodextrin simulation enzyme functional fibre
CN100392172C (en) * 2006-09-21 2008-06-04 浙江理工大学 Preparation method of cyclodextrin polymer simulation enzyme functional fibre
CN101220557B (en) * 2007-12-06 2010-06-02 浙江理工大学 Method for manufacturing mimetic enzyme catalysis fibre
AT506334B1 (en) * 2008-01-22 2010-12-15 Chemiefaser Lenzing Ag METHOD FOR THE TREATMENT OF CELLULOSIC FORM BODIES
AT509289B1 (en) * 2009-12-28 2014-06-15 Chemiefaser Lenzing Ag FUNCTIONALIZED CELLULOSIC FORM BODY AND METHOD FOR THE PRODUCTION THEREOF
JP4832573B2 (en) * 2010-02-27 2011-12-07 慶一郎 金久 Antiviral and antibacterial processing methods for textile structures

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5102564A (en) * 1989-04-12 1992-04-07 The Procter & Gamble Company Treatment of fabric with perfume/cyclodextrin complexes
US5534165A (en) * 1994-08-12 1996-07-09 The Procter & Gamble Company Fabric treating composition containing beta-cyclodextrin and essentially free of perfume
DE4429229A1 (en) * 1994-08-18 1996-02-22 Consortium Elektrochem Ind Cyclodextrin derivatives with at least one nitrogen-containing heterocycle, their production and use
DE19520967A1 (en) * 1995-06-08 1996-12-12 Consortium Elektrochem Ind Treatment of leather, synthetic or natural textiles
WO1998026808A2 (en) * 1996-12-17 1998-06-25 The Procter & Gamble Company Absorbent articles with odor control system
AT2256U1 (en) * 1997-10-15 1998-07-27 Chemiefaser Lenzing Ag METHOD FOR TREATING CELLULOSIC MOLDED BODIES

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ATA20122001A (en) 2005-11-15
TW200301325A (en) 2003-07-01
ATE483848T1 (en) 2010-10-15
KR20040070238A (en) 2004-08-06
AT413988B (en) 2006-08-15
TWI273148B (en) 2007-02-11
AU2002361375A8 (en) 2003-07-09
WO2003054283A2 (en) 2003-07-03
EP1463858A2 (en) 2004-10-06
CN1604979A (en) 2005-04-06
WO2003054283A3 (en) 2004-08-05
KR100910989B1 (en) 2009-08-05
AU2002361375A1 (en) 2003-07-09
CN1311123C (en) 2007-04-18
DE50214703D1 (en) 2010-11-18
JP2005535790A (en) 2005-11-24

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