EP1630280A1 - Process for the treatment of textile fabrics - Google Patents
Process for the treatment of textile fabrics Download PDFInfo
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- 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
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- Prior art keywords
- solution
- radical
- silicon compounds
- ammonia
- silicon compound
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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
- 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
- D06M13/50—Treating 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
- D06M13/51—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond
- D06M13/513—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond with at least one carbon-silicon bond
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- 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
- D06M11/00—Treating 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
- D06M11/58—Treating 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
- D06M11/59—Treating 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
- D06M11/61—Liquid ammonia
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- 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
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
-
- 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
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- 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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/20—Treatment 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
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- 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)
Abstract
Description
Die Erfindung betrifft ein Verfahren zur Behandlung von textilen Flächengebilden, wobei auf die Flächengebilde eine bestimmte Siliciumverbindung oder ein Gemisch von Siliciumverbindungen aufgebracht und anschließend die Flächengebilde getrocknet werden.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.
Es ist bekannt, textile Flächengebilde, welche Cellulosefasern enthalten oder welche zu 100 % aus Cellulosefasern bestehen, mit flüssigem Ammoniak zu behandeln. Dies wird üblicherweise durchgeführt bei textilen Flächengebilden, welche einer sogenannten Feuchtvernetzung unterworfen werden sollen.
Es ist ebenfalls bekannt, textile Flächengebilde aus cellulosischen Materialien mit Cellulosevernetzern zu behandeln, um das Knitterverhalten der fertigen Artikel günstig zu beeinflussen. Zu diesem Zweck werden die textilen Flächengebilde im Rahmen eines Ausrüst- bzw. Veredlungsverfahrens üblicherweise mittels eines Foulardprozesses ausgerüstet. Die Foulardierungsflotte ist hierbei im Normalfall eine wässrige Lösung oder Dispersion. Diese Lösung oder Dispersion enthält einen oder mehrere Cellulosevernetzer sowie gegebenenfalls weitere erwünschte Bestandteile wie z.B. Weichgriffmittel.
Als Cellulosevernetzer sind dem Fachmann unter anderem N-Methylolverbindungen bekannt. Diese führen zwar zu guten Vernetzungsergebnissen, jedoch kann sich störend auswirken, dass sie Formaldehyd als Nebenprodukt enthalten oder bei erhöhter Temperatur oder bei Lagerung freisetzen. Es wurden Alternativprodukte als Vernetzer gesucht, welche Formaldehyd weder enthalten noch bei der Verarbeitung freisetzen. Dabei wurde gefunden, dass eine Vernetzung von Cellulosefasern auch durch Behandlung mittels Silanen erfolgen kann.
Verfahren, bei denen Silane als Cellulosevernetzer verwendet werden, sind bekannt. So beschreiben die US 3 055 774, die EP-A 563 961 und die EP-A 401 668 die Behandlung von Cellulose oder Cellulosederivaten mit funktionellen Silanen. In all diesen Verfahren wird das Silan in Form einer wässrigen Zusammensetzung verwendet.It is known to treat textile fabrics which contain cellulose fibers or which consist of 100% cellulose fibers with liquid ammonia. This is usually carried out in textile fabrics which are to be subjected to a so-called wet crosslinking.
It is also known to treat textile fabrics made of cellulosic materials with cellulose crosslinkers in order to favorably influence the creasing behavior of the finished articles. For this purpose, the textile fabrics are usually equipped by means of a foulard process as part of a finishing or finishing process. The padding liquor is in this case normally an aqueous solution or dispersion. This solution or dispersion contains one or more cellulose crosslinkers and optionally other desired ingredients such as softener agents.
As 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.
Es hat sich gezeigt, dass die Vernetzung von Celluloseartikeln mit wässrigen Systemen, welche Silane enthalten, in einer Reihe von Fällen nicht zu optimalen Vernetzungsergebnissen führt, was beispielsweise Knittererholung, Wasserrückhaltevermögen usw. betrifft. Ferner ist die Verwendung bestimmter reaktiver Silane zur Vernetzung mittels wässriger Systeme gar nicht möglich, weil diese Silane mit Wasser reagieren oder in wässrigen Systemen keine optimale Reaktivität gegenüber Cellulose aufweisen. Hierunter fallen z.B. Silane, in denen Alkoxygruppen an das Siliciumatom gebunden sind. Andererseits wäre gerade der Einsatz solcher Silane als Vernetzer wegen ihrer Reaktivität gegenüber Cellulose wünschenswert.It has been found that the cross-linking of cellulose articles with aqueous systems containing silanes does not lead to optimal cross-linking results in a number of cases, such as wrinkle recovery, water retention, and the like. Furthermore, the use of certain reactive silanes for crosslinking by means of aqueous systems is not possible at all, because these silanes react with water or have no optimal reactivity with cellulose in aqueous systems. These include e.g. Silanes in which alkoxy groups are bonded to the silicon atom. On the other hand, it would be desirable to use such silanes as crosslinkers because of their reactivity with cellulose.
Die Aufgabe, welche der vorliegenden Erfindung zugrunde lag, bestand darin, ein Verfahren zu entwickeln, mittels dessen eine hocheffektive Vernetzung textiler Flächengebilde, die erhebliche Mengen an Cellulosefasern enthalten, durchgeführt werden kann. Ferner sollte das Verfahren es gestatten, als Vernetzer auch solche Siliciumverbindungen zu verwenden, welche in wäßrigen Systemen instabil sind oder nicht optimale Reaktivität besitzen.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.
Die Aufgabe wurde gelöst durch ein Verfahren zur Behandlung von textilen Flächengebilden, welche zu 70 bis 100 Gew% aus Cellulosefasern bestehen, mit einer Lösung einer Siliciumverbindung oder eines Gemischs von Siliciumverbindungen in flüssigem Ammoniak, wobei diese Lösung auf das textile Flächengebilde aufgebracht und anschließend das Flächengebilde getrocknet wird,
wobei mindestens eine der verwendeten Siliciumverbindungen einer der Formeln (I) bis (IV) entspricht.
(RO)nSi(R1)4-n (I)
(RO)tSi(R1)4-t-y(R2)y (II)
wobei
alle Reste R unabhängig voneinander für Wasserstoff oder einen Alkylrest mit 1 bis 4 Kohlenstoffatomen stehen,
alle Reste R1 unabhängig voneinander für einen Alkylrest mit 1 bis 18 Kohlenstoffatomen oder
den Phenylrest stehen,
der Rest R2 für einen Rest der Formel (V) oder der Formel (Vl) steht
wobei Ep für den einwertigen von Ethylenoxid abgeleiteten Rest oder für einen Epoxycyclohexylrest, vorzugsweise für den 3,4-Epoxy-1-cyclohexylrest, steht,
wobei
n eine Zahl von 2 bis 4 ist,
a eine Zahl von 1 bis 3 ist,
b den Wert 3― a besitzt,
c eine Zahl von 1 bis 4, vorzugsweise 2, ist,
d eine Zahl von 1 bis 5 ist,
e eine Zahl von 1 bis 4, vorzugsweise 1 oder 3 ist,
t eine Zahl von 1 bis 3
y eine Zahl von 1 bis 3, vorzugsweise 1, ist
t + y eine Zahl von 2 bis 4 ist.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).
(RO) n Si (R 1 ) 4-n (I)
(RO) t Si (R 1 ) 4-ty (R 2 ) y (II)
in which
all radicals R independently of one another represent hydrogen or an alkyl radical having 1 to 4 carbon atoms,
all radicals R 1 are independently an alkyl radical having 1 to 18 carbon atoms or
the phenyl radical,
the radical R 2 is a radical of the formula (V) or of the formula (VI)
where Ep is the monovalent radical derived from ethylene oxide or an epoxycyclohexyl radical, preferably the 3,4-epoxy-1-cyclohexyl radical,
in which
n is a number from 2 to 4,
a is a number from 1 to 3,
b has the value 3- a,
c is a number from 1 to 4, preferably 2,
d is a number from 1 to 5,
e is a number from 1 to 4, preferably 1 or 3,
t is a number from 1 to 3
y is a number from 1 to 3, preferably 1
t + y is a number from 2 to 4.
Mittels des erfindungsgemäßen Verfahrens werden textile Flächengebilde behandelt, welche zu 70 bis 100 Gew% aus Cellulosefasern bestehen. Als textile Flächengebilde kommen Gewebe, Maschenware und Vliese (nonwovens) in Frage. Bevorzugt sind hierbei Gewebe.
Die textilen Flächengebilde enthalten 70 bis 100 Gew% Cellulosefasern. Falls es sich nicht um Material aus 100 % Cellulosefasern handelt, kann der Rest aus synthetischen Fasern wie z.B. Polyester oder Polyamid bestehen. Die Cellulosefasern können aus natürlicher Cellulose wie z.B. Baumwolle oder auch aus regenierter Cellulose bestehen.
Die nach dem erfindungsgemäßen Verfahren behandelten textilen Flächengebilde können unter anderem zu Bekleidungsartikeln weiterverarbeitet werden.By means of the process according to the invention, 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.
Das erfindungsgemäße Verfahren weist eine Reihe von Vorteilen auf:
- a) die Effektivität der Vernetzung ist hoch; vielfach ist sie höher als für den Fall, dass man die Vernetzung mit den gleichen Siliciumverbindungen, aber in wässrigem Medium durchführt.
- b) es können auch Silane verwendet werden, die hohe Reaktivität gegenüber Cellulose aufweisen, die jedoch nicht in Form wässriger Systeme einsetzbar sind, weil in diesen wässrigen Systemen die Silane nicht stabil oder zu wenig reaktiv sind.
- c) in denjenigen Fällen, wo ohnehin eine Behandlung der textilen Flächengebilde mit flüssigem Ammoniak vorgesehen ist, kann vielfach eine Verarbeitungsstufe eingespart werden, nämlich ein separater Ausrüstungsvorgang zwecks Applikation eines Cellulosevernetzers, da der Vernetzer bereits (in Form einer Lösung in flüssigem Ammoniak) aufgebracht wurde.
Andererseits ist es natürlich auch möglich, dennoch einen separaten Ausrüstungs- bzw. Veredlungsprozeß durchzuführen, z.B. dann, wenn nach Durchlaufen des erfindungsgemäßen Verfahrens weitere Produkte in Form wässriger Lösungen oder Dispersionen aufgebracht werden sollen. Solche Produkte können unter anderem Weichgriffmittel, Fluorpolymere oder flammhemmende Mittel sein, wie sie dem Fachmann auf dem Gebiet der Textilausrüstung bekannt sind. - d) nach Durchführung des erfindungsgemäßen Verfahrens kann auf eine übliche Feuchtvernetzung verzichtet werden. Es ist also bevorzugt, anschließend keine Feuchtvernetzung mehr durchzuführen. Vielmehr führt das erfindungsgemäße Verfahren nach Trocknung und gegebenenfalls Kondensation bereits zu sehr guten Vernetzungsergebnissen. Dies läßt sich durch die unten beschriebene Bestimmung der Knittereigenschaften über Bestimmung der Naß-Knitterwinkel feststellen.
- e) das erfindungsgemäße Verfahren kann ohne die Verwendung von Produkten durchgeführt werden, die Formaldehyd enthalten oder bei erhöhter Temperatur freisetzen.
- a) the effectiveness of crosslinking is high; in many cases, it is higher than in the case where one carries out the crosslinking with the same silicon compounds, but in an aqueous medium.
- b) it is also possible to use silanes which have high reactivity towards cellulose, but which can not be used in the form of aqueous systems, because in these aqueous systems the silanes are not stable or too less reactive.
- c) in those cases where anyway a treatment of textile fabrics with liquid ammonia is provided, often a processing stage can be saved, namely a separate finishing process for the application of a cellulose crosslinker, since the crosslinker has already been applied (in the form of a solution in liquid ammonia) ,
On the other hand, it is of course also possible to perform a separate finishing or finishing process, for example, if after passing through the process according to the invention further products in the form of aqueous solutions or dispersions are to be applied. Such products may include, but are not limited to, softeners, fluoropolymers or flame retardants known to those skilled in the textile finishing art. - d) after carrying out the method according to the invention can be dispensed with a conventional moisture crosslinking. It is therefore preferable not to carry out any more moisture crosslinking afterwards. Rather, the process according to the invention after drying and optionally condensation already leads to very good crosslinking results. This can be determined by the determination of wrinkling properties described below by determining the wet wrinkle angle.
- e) the inventive method can be carried out without the use of products containing formaldehyde or release at elevated temperature.
Bei dem erfindungsgemäßen Verfahren werden die genannten textilen Flächengebilde mit einer Lösung einer Siliciumverbindung der nachfolgend beschriebenen Art in flüssigem Ammoniak behandelt. An Stelle einer einzigen Siliciumverbindung kann auch ein Gemisch von Siliciumverbindungen verwendet werden. Mindestens eine der verwendeten Siliciumverbindungen entspricht hierbei einer der unten erläuterten Formeln (I) bis (lV). Vorzugsweise fallen alle verwendeten Siliciumverbindungen unter eine dieser Formeln, es ist also bevorzugt, dass keine Siliciumverbindungen anwesend sind, die keiner der Formeln (I) bis (IV) entsprechen, gegebenenfalls jedoch können in der Lösung in flüssigem Ammoniak zusätzlich aminofunktionelle Polysiloxane oder andere Weichgriffmittel anwesend sein. Es müssen jedoch alle verwendeten Siliciumverbindungen bzw. anderen Weichgriffmittel in flüssigem Ammoniak gut löslich sein.In the method according to the invention, said textile fabrics are treated with a solution of a silicon compound of the type described below in liquid ammonia. Instead of a single silicon compound, 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. Preferably, 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. However, all silicon compounds or other softening agents used must be readily soluble in liquid ammonia.
Das Aufbringen der ammoniakalischen Lösung auf die textilen Flächengebilde kann nach Methoden erfolgen, wie sie in der Textilindustrie bekannt sind. Gut geeignet ist eine Applikation mittels eines Bades, z.B. entsprechend einer Foulard-Applikation, bei der die Flächengebilde in eine Lösung der gewünschten Silicium-Verbindung in flüssigem Ammoniak getaucht werden. Die Verweilzeit des textilen Flächengebildes in der ammoniakalischen Lösung beträgt im Normalfall ca. 20 Sekunden bis 20 Minuten, kann jedoch auch länger sein. Anschließend wird in bekannter Weise abgequetscht.
Die Lösung der entsprechenden Siliciumverbindung oder des Gemischs von Siliciumverbindungen besitzt bei der Applikation auf das Flächengebilde vorzugsweise eine Temperatur im Bereich von -60°C bis -40°C. Dies gilt unabhängig davon, nach welcher Methode appliziert wird. Die Ammoniak-Lösung enthält im Normalfall etwa 0,01 bis 3, vorzugsweise 0,1 bis 0,7 Gewichtsteile Siliciumverbindung pro 100 Gewichtsteilen Ammoniak. Diesen Zahlenangaben liegt die Gesamtmenge aller verwendeten Siliciumverbindungen zugrunde, welche unter eine der Formeln (I) bis (IV) fallen.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).
Es ist besonders vorteilhaft und deshalb bevorzugt, wenn die Lösung der Siliciumverbindung bzw. der Siliciumverbindungen in flüssigem Ammoniak zusätzlich einen Katalysator enthält. Geeignete Katalysatoren bewirken ein erhöhtes Maß an Vernetzung und damit bessere Effekte bezüglich Knitterverhalten der fertigen Textilien und/oder dessen Permanenz. Als Katalysatoren gut geeignet sind sterisch gehinderte Amine wie z.B. Diaza-bicyclo [2.2.2]-octan (DABCO) oder 4-dimethylaminopyridin (4-DMAP). Die Menge an zugegebenem Katalysator beträgt vorzugsweise 1,0 bis 3 Gew.%, bezogen auf die Gesamtmenge der in der ammoniakalischen Lösung anwesenden Siliciumverbindungen der Formeln (I) bis (IV).It is particularly advantageous and therefore preferred if 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.
Nach der Applikation der ammoniakalischen Lösung müssen die textilen Flächengebilde getrocknet werden. Dies kann mit bekannten Trocknungsapparaturen durchgeführt werden. Die Trocknung erfolgt im Normalfall bei einer Temperatur im Bereich von 60°C bis 180°C, vorzugsweise von 80°C bis 150°C und wird so lange durchgeführt, bis Ammoniak, Wasser und ggf. gebildeter Alkohol entfernt sind. Normalerweise ist hierfür eine Trocknungszeit von etwa 5 bis 30 Minuten erforderlich. Im Fall der Verwendung von Siliciumverbindungen, in denen OH oder OR-Gruppen an Siliciumatome gebunden sind, entsteht nämlich bei der Vernetzungsreaktion mit OH-Gruppen der Cellulose Wasser oder Alkohol.
Vielfach ist es von Vorteil, wenn an den textilen Flächengebilden vor der Trocknung noch ein Sanfor-Prozeß durchgeführt wird. Hierunter versteht man ein mechanisches Schrumpfen textiler Ware wie z.B. in "K. Peter, H.K. Rouette. Grundlagen der Textilveredelung, 13. Auflage, dfv Deutscher Fachverlag 1989, Frankfurt am Main, insbesondere Seiten 718 bis 721, beschrieben. Nach der Trocknung der textilen Flächengebilde kann, wenn gewünscht, noch eine Rückbefeuchtung mit Wasser erfolgen.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. Peter, HK Rouette, Grundlagen der Textilveredelung, 13th edition, dfv Deutscher Fachverlag 1989, Frankfurt am Main, in particular pages 718 to 721. After the textile fabrics have dried If desired, it can be re-moistened with water.
In einer bevorzugten Ausführungsform des erfindungsgemäßen Verfahrens wird nach der Trocknung des textilen Flächengebildes noch eine Kondensation durchgeführt, insbesondere dann, wenn die Trocknungstemperatur unterhalb von 130°C liegt. Dies ist eine Behandlung bei höherer Temperatur, z.B. im Bereich von 130°C bis 180°C, vorzugsweise 140°C bis 170°C, während einer Zeit von 2 bis 10 Minuten. Durch die Kondensation lässt sich die Anzahl der Bindungen erhöhen, die sich zwischen Cellulose und den reaktiven Siliciumverbindungen ausbilden.In a preferred embodiment of the process according to the invention, 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.
Mindestens eine der für das erfindungsgemäße Verfahren verwendeten Siliciumverbindungen muß einer der Formeln (I) bis (lV) entsprechen.
(RO)nSi(R1)4-n (I)
(RO)tSi(R1)4-t-y(R2)y (II)
(RO) n Si (R 1 ) 4-n (I)
(RO) t Si (R 1 ) 4-ty (R 2 ) y (II)
In diesen Formeln bedeuten:
- alle Reste R unabhängig voneinander entweder Wasserstoff oder einen Alkylrest mit 1 bis 18 Kohlenstoffatomen. Vorzugsweise stehen alle anwesenden Reste R für einen Alkylrest mit 1 bis 4 Kohlenstoffatomen. Dieser kann linear oder verzweigt sein. Bevorzugt stehen alle Reste R unabhängig voneinander für eine Methyl- oder eine Ethylgruppe.
- alle Reste R1 unabhängig voneinander einen Alkylrest mit 1 bis 18 Kohlenstoffatomen oder den unsubstituierten Phenylrest. Vorzugsweise stehen alle Reste R1 entweder für den Methyl- oder den Ethylrest.
- der Rest R2 einen Rest der Formel (V) oder der Formel (Vl)
- Ep den einwertigen Rest, der sich von Ethylenoxid ableitet, also den Rest, der entsteht, wenn ein Wasserstoffatom aus der Formel für Ethylenoxid (Oxiran) entfernt wird oder einen Epoxycyclohexylrest, vorzugsweise den 3,4-Epoxy-1-cyclohexylrest
n eine Zahl von 2 bis 4
a eine Zahl von 1 bis
b =3-a
c eine Zahl von 1 bis 4, vorzugsweise 2
d eine Zahl von 1 bis 5
e eine Zahl von 1 bis 4, vorzugsweise 1 oder 3,
t eine Zahl von 1 bis 3
y eine Zahl von 1 bis 3, vorzugsweise 1,
t + y eine Zahl von 2 bis 4.
- all radicals R are independently of one another either hydrogen or an alkyl radical having 1 to 18 carbon atoms. Preferably, all radicals R present are an alkyl radical having 1 to 4 carbon atoms. This can be linear or branched. Preferably, all radicals R independently of one another are a methyl or an ethyl group.
- all radicals R 1 independently of one another are an alkyl radical having 1 to 18 carbon atoms or the unsubstituted phenyl radical. Preferably, all radicals R 1 are either the methyl or the ethyl radical.
- the radical R 2 is a radical of the formula (V) or of the formula (VI)
- Ep is the monovalent residue derived from ethylene oxide, that is, the balance that results when a hydrogen atom is removed from the formula for ethylene oxide (oxirane) or an epoxycyclohexyl radical, preferably the 3,4-epoxy-1-cyclohexyl radical
n is a number from 2 to 4
a is a number from 1 to
b = 3-a
c is a number from 1 to 4, preferably 2
d is a number from 1 to 5
e is a number from 1 to 4, preferably 1 or 3,
t is a number from 1 to 3
y is a number from 1 to 3, preferably 1,
t + y is a number from 2 to 4.
Es hat sich gezeigt, dass in vielen Fällen optimale Knittereigenschaften resultieren, wenn c=2.It has been shown that in many cases optimal crumple properties result when c = 2.
Alle diese Siliciumverbindungen enthalten 2 oder mehr reaktive Gruppen, welche mit OH-Gruppen der Cellulose reagieren können, gegebenenfalls bei erhöhter Temperatur. Das Ergebnis dieser Reaktion ist eine Quervernetzung von Celluloseketten, die eine Verbesserung des Knitterverhaltens zur Folge hat.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.
Siliciumverbindungen bzw. Silane der Formeln (I) bis (IV) und ihre Herstellung sind aus dem Stand der Technik bekannt, z.B. aus den eingangs genannten Schriften und aus der EP-A 1 199 339 oder durch dem Fachmann bekannte Verfahren herstellbar, z.B. durch Umsetzung von Halogensilanen mit Alkoholen. Ferner sind Siliciumverbindungen der Formeln (I) bis (lV) auf dem Markt erhältlich, z.B. von der Firma Wacker, DE.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.
Nach Durchführung des erfindungsgemäßen Verfahrens können textile Flächengebilde erhalten werden, die ausgezeichnete Eigenschaften bezüglich Knitterverhalten und Wasserrückhaltevermögen aufweisen, wobei diese Eigenschaften gute Permanenz gegenüber Lagerung und Waschvorgängen besitzen.After carrying out the process according to the invention, it is possible to obtain textile fabrics which have excellent properties with regard to creasing behavior and water retention, these properties having good permanence against storage and washing processes.
In "Melliand Textilberichte", Vol 39, Nr. 5, Seiten 552― 554, ist ein Messgerät zur Bestimmung der Naß-Knitterwinkel (auch "Knittererholungswinkel naß" genannt) beschrieben. Mit Hilfe dieses Geräts lässt sich das Knitterverhalten textiler Flächengebilde bestimmen. Den unten in den Ausführungsbeispielen 1a) bis 1d) angegebenen Werten für den Knittererholungswinkel naß liegen Bestimmungen gemäß dieses Melliand-Zitats zugrunde.
Zu dieser Bestimmung wurden die Proben folgendermaßen vorbereitet:
Gewebeproben von 2 cm × 1 cm wurden in eine wässrige Lösung gegeben, die 1g/l an Netzmittel (Natriumsalz eines Alkylnaphthalinsulfonats) enthielt. Nach 5 Minuten wurden die Proben entnommen, auf eine Kunststoffschiene gelegt, gefaltet und 3 Minuten mit einem 500 g-Gewicht belastet. Anschließend wurde 3 Minuten lang entlastet und dann der Knittererholungswinkel gemessen.In "Melliand Textilberichte", Vol 39, No. 5, pages 552-554, 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.
In einer Apparatur werden 25 ml Ammoniak bei einer Temperatur von ―40°C bzw. ―60°C einkondensiert und 0,1 ml Alkoxysilan zugegeben und homogen vermischt. Die Art des Alkoxysilans wurde in verschiedenen Versuchen variiert und geht aus den Tabellen 1 bis 4 hervor. In manchen Versuchen wurde ein gehindertes Amin als Katalysator zugegeben. Anschließend wird ein Gewebe zugegeben, nach definierter Zeit wieder entfernt und auf Raumtemperatur gebracht. Nach Abdampfen des Ammoniaks wird das Flächengebilde im Trockenschrank getrocknet und gegebenenfalls kondensiert. Das verwendete Gewebe war in allen Beispielen 1a) bis 1d) aus 100% Baumwolle.In an apparatus 25 ml of ammonia are condensed at a temperature of -40 ° C and -60 ° C and 0.1 ml of alkoxysilane was added and mixed homogeneously. The nature of the alkoxysilane was varied in various experiments and is shown in Tables 1 to 4. In some experiments, a hindered amine was added as a catalyst. Subsequently, a tissue is added, removed again after a defined time and brought to room temperature. After evaporation of the ammonia, the fabric is dried in a drying oven and optionally condensed. The fabric used was 100% cotton in all examples 1a) to 1d).
Nachfolgend werden die Bedingungen der Versuche zu den Beispielen 1a) bis 1d) in Tabellenform dargestellt. Bei diesen 4 Beispielen wurde jeweils eine unterschiedliche Siliciumverbindung (Alkoxysilan) eingesetzt. Dort wo ein Katalysator mitverwendet wurde, betrug dessen Menge jeweils 2,5 Gew%, bezogen auf die Siliciumverbindung.The conditions of the experiments for examples 1a) to 1d) are shown in tabular form below. In these 4 examples, a different silicon compound (alkoxysilane) was used in each case. Wherever a catalyst was used, its amount was in each case 2.5% by weight, based on the silicon compound.
In den Tabellen bedeuten höhere Werte für "Knittererholungswinkel naß" ein verbessertes Knittererholungsverhalten.In the tables, higher values for " crease recovery angle wet" mean improved crease recovery performance.
Claims (8)
wobei mindestens eine der verwendeten Siliciumverbindungen einer der Formeln (I) bis (IV) entspricht.
(RO)nSi(R1)4-n (I)
(RO)tSi(R1)4-t-y(R2)y (II)
wobei
alle Reste R unabhängig voneinander für Wasserstoff oder einen Alkylrest mit 1 bis 4 Kohlenstoffatomen stehen,
alle Reste R1 unabhängig voneinander für einen Alkylrest mit 1 bis 18 Kohlenstoffatomen oder den Phenylrest stehen,
der Rest R2 für einen Rest der Formel (V) oder der Formel (VI) steht
wobei Ep für den einwertigen von Ethylenoxid abgeleiteten Rest oder für einen Epoxycyclohexylrest, vorzugsweise für den 3,4-Epoxy-1-cyclohexylrest, steht,
wobei
n eine Zahl von 2 bis 4 ist,
a eine Zahl von 1 bis 3 ist,
b den Wert 3 ― a besitzt,
c eine Zahl von 1 bis 4, vorzugsweise 2, ist,
d eine Zahl von 1 bis 5 ist,
e eine Zahl von 1 bis 4, vorzugsweise 1 oder 3 ist,
t eine Zahl von 1 bis 3
y eine Zahl von 1 bis 3, vorzugsweise 1, ist
t + y eine Zahl von 2 bis 4 ist.Process for the treatment of textile fabrics consisting 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).
(RO) n Si (R 1 ) 4-n (I)
(RO) t Si (R 1 ) 4-ty (R 2 ) y (II)
in which
all radicals R independently of one another represent hydrogen or an alkyl radical having 1 to 4 carbon atoms,
all radicals R 1 independently of one another are an alkyl radical having 1 to 18 carbon atoms or the phenyl radical,
the radical R 2 is a radical of the formula (V) or of the formula (VI)
where Ep is the monovalent radical derived from ethylene oxide or an epoxycyclohexyl radical, preferably the 3,4-epoxy-1-cyclohexyl radical,
in which
n is a number from 2 to 4,
a is a number from 1 to 3,
b has the value 3 - a,
c is a number from 1 to 4, preferably 2,
d is a number from 1 to 5,
e is a number from 1 to 4, preferably 1 or 3,
t is a number from 1 to 3
y is a number from 1 to 3, preferably 1
t + y is a number from 2 to 4.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04020579A EP1630280A1 (en) | 2004-08-31 | 2004-08-31 | Process for the treatment of textile fabrics |
| EP05768410A EP1792002A1 (en) | 2004-08-31 | 2005-08-06 | Treatment of textile fabrics |
| KR1020077005013A KR20070047817A (en) | 2004-08-31 | 2005-08-06 | Treatment of textile fabrics |
| PCT/EP2005/008552 WO2006024364A1 (en) | 2004-08-31 | 2005-08-06 | Treatment of textile fabrics |
| CNA2005800289843A CN101010457A (en) | 2004-08-31 | 2005-08-06 | Treatment of textile fabrics |
| US11/659,528 US20080115290A1 (en) | 2004-08-31 | 2005-08-06 | Treatment Of Textile Fabrics |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04020579A EP1630280A1 (en) | 2004-08-31 | 2004-08-31 | Process for the treatment of textile fabrics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1630280A1 true EP1630280A1 (en) | 2006-03-01 |
Family
ID=34926356
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP04020579A Withdrawn EP1630280A1 (en) | 2004-08-31 | 2004-08-31 | Process for the treatment of textile fabrics |
| EP05768410A Withdrawn EP1792002A1 (en) | 2004-08-31 | 2005-08-06 | Treatment of textile fabrics |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP05768410A Withdrawn EP1792002A1 (en) | 2004-08-31 | 2005-08-06 | Treatment of textile fabrics |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20080115290A1 (en) |
| EP (2) | EP1630280A1 (en) |
| KR (1) | KR20070047817A (en) |
| CN (1) | CN101010457A (en) |
| WO (1) | WO2006024364A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015131965A1 (en) * | 2014-03-04 | 2015-09-11 | Henkel Ag & Co. Kgaa | Raw material and use thereof to reduce creases in textiles |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US11098444B2 (en) | 2016-01-07 | 2021-08-24 | Tommie Copper Ip, Inc. | Cotton performance products and methods of their manufacture |
| CN109944062B (en) * | 2019-03-05 | 2021-04-27 | 武汉纺织大学 | Liquid ammonia swelling and in-situ controllable non-ironing finishing method for cotton fabric |
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| 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 (en) * | 1980-02-28 | 1981-12-03 | Chemiefaser Lenzing AG, 4860 Lenzing, Oberösterreich | METHOD FOR PRODUCING NEW O-TRIMETHYLSILYL CELLULOSES |
| DE19511112A1 (en) * | 1995-03-25 | 1996-09-26 | Pfersee Chem Fab | Treatment of cellulose, esp. cotton, fabric, |
| EP0900874A2 (en) * | 1997-09-08 | 1999-03-10 | Nisshinbo Industries Inc. | Method for processing cellulose fiber-containing textile fabrics |
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| 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 (en) * | 1981-09-24 | 1985-07-02 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for modifying regenerated cellulose fiber |
| US5032682A (en) * | 1989-06-05 | 1991-07-16 | Aqualon Company | Silated polysaccharides |
| 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 |
| DE4211256A1 (en) * | 1992-04-03 | 1993-10-07 | Wacker Chemie Gmbh | Crosslinkable composition based on aminosilicone |
| FR2770232B1 (en) * | 1997-10-27 | 2000-01-14 | Rhodia Ag Rhone Poulenc | PROCESS FOR THE PREPARATION OF A REGENERATED CELLULOSE FIBER OR YARN |
-
2004
- 2004-08-31 EP EP04020579A patent/EP1630280A1/en not_active Withdrawn
-
2005
- 2005-08-06 EP EP05768410A patent/EP1792002A1/en not_active Withdrawn
- 2005-08-06 CN CNA2005800289843A patent/CN101010457A/en active Pending
- 2005-08-06 US US11/659,528 patent/US20080115290A1/en not_active Abandoned
- 2005-08-06 KR KR1020077005013A patent/KR20070047817A/en not_active Application Discontinuation
- 2005-08-06 WO PCT/EP2005/008552 patent/WO2006024364A1/en active Application Filing
Patent Citations (4)
| 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 (en) * | 1980-02-28 | 1981-12-03 | Chemiefaser Lenzing AG, 4860 Lenzing, Oberösterreich | METHOD FOR PRODUCING NEW O-TRIMETHYLSILYL CELLULOSES |
| DE19511112A1 (en) * | 1995-03-25 | 1996-09-26 | Pfersee Chem Fab | Treatment of cellulose, esp. cotton, fabric, |
| EP0900874A2 (en) * | 1997-09-08 | 1999-03-10 | Nisshinbo Industries Inc. | Method for processing cellulose fiber-containing textile fabrics |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015131965A1 (en) * | 2014-03-04 | 2015-09-11 | Henkel Ag & Co. Kgaa | Raw material and use thereof to reduce creases in textiles |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2006024364A1 (en) | 2006-03-09 |
| CN101010457A (en) | 2007-08-01 |
| KR20070047817A (en) | 2007-05-07 |
| EP1792002A1 (en) | 2007-06-06 |
| US20080115290A1 (en) | 2008-05-22 |
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