Nothing Special   »   [go: up one dir, main page]

EP0339179A2 - Finishing composition for textile fibres or for textile products - Google Patents

Finishing composition for textile fibres or for textile products Download PDF

Info

Publication number
EP0339179A2
EP0339179A2 EP89100606A EP89100606A EP0339179A2 EP 0339179 A2 EP0339179 A2 EP 0339179A2 EP 89100606 A EP89100606 A EP 89100606A EP 89100606 A EP89100606 A EP 89100606A EP 0339179 A2 EP0339179 A2 EP 0339179A2
Authority
EP
European Patent Office
Prior art keywords
organopolysiloxane
units
radical
groups
quaternary ammonium
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.)
Granted
Application number
EP89100606A
Other languages
German (de)
French (fr)
Other versions
EP0339179A3 (en
EP0339179B1 (en
Inventor
Dietmar Dr. Schaefer
Friedhelm Nickel
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.)
Evonik Operations GmbH
Original Assignee
TH Goldschmidt AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by TH Goldschmidt AG filed Critical TH Goldschmidt AG
Publication of EP0339179A2 publication Critical patent/EP0339179A2/en
Publication of EP0339179A3 publication Critical patent/EP0339179A3/en
Application granted granted Critical
Publication of EP0339179B1 publication Critical patent/EP0339179B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • D06M15/19—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
    • D06M15/647—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing polyether sequences

Definitions

  • the invention relates to an agent for finishing textile fibers or products consisting of textile fibers, such as woven, knitted or nonwoven.
  • the invention relates in particular to an agent for the hydrophilizing softening of textile fibers or products consisting of textile fibers based on aqueous preparations of organosilicon compounds.
  • Organosilicon compounds are used to a considerable extent in the finishing of textile yarns and textiles. According to their respective structure and modification, the organosilicon compounds act as plasticizers, anti-foaming agents, water repellents, finishing agents and as agents for improving the feel. Due to the possibility of modifying organosiloxanes with functional organic groups, the silicones can be adapted to the respective purpose.
  • the object of the present invention is to provide means for finishing textile fibers or products consisting of textile fibers find which are able to improve the grip of the finished fibers or fiber products with simultaneous hydrophilization.
  • the improvement in the grip should also be achieved with twisted open-end yarns.
  • the agents wet the textile material well and penetrate into the fiber structure, whereby the wetting and penetration should also be ensured when finishing hydrophobic textile material.
  • the products are said to impart good hydrophilicity to the textile materials, in order to ensure that the finished textile fibers or textiles can be recolored or recolored without problems and also have good anti-electrostatic properties.
  • a further requirement for the desired finishing agents is that they have high bath stability in the form of the aqueous preparation, i.e. do not separate even after prolonged storage and during use, especially when diluted, and are compatible with other conventional finishing aids.
  • an agent which is characterized according to the invention contains 0.5 to 80% by weight of a mixture of modified organopolysiloxanes A and B in a weight ratio A: B of 10: 1 to 1: 1, where the organopolysiloxane A is a linear siloxane containing polyether groups and having at least 40 dialkylsiloxy units, to which at least 2 polyether groups with a molecular weight of 600 to 4000 each, which consist of 40 to 100 mol% oxyethylene units, the remainder to 100 mol% oxypropylene units, are bound, and the ratio of the number of dialkylsiloxy units: number of polyether groups ⁇ 8, and the organopolysiloxane B is a quaternary ammonium group-containing linear siloxane with at least 20 dialkylsiloxy units to which at least 2 quaternary ammonium groups are bonded via carbon, and the ratio of the number of dialkylsiloxy units: number
  • the agent preferably consists of 0.5 to 80 wt .-% of the organopolysiloxane mixture A, B and 20 to 99.5 wt .-% water and / or a water-miscible organic solvent.
  • Linear polysiloxanes containing polyether groups have been known for a long time and are also used for textile finishing purposes, to improve the feel and as a wetting agent.
  • Organosilicon compounds with quaternary ammonium groups are also known from the prior art, which are used in particular to reduce the static charge on textiles.
  • organopolysiloxanes A defined above linear siloxanes containing polyether groups
  • organopolysiloxanes B linear siloxanes containing quaternary ammonium groups
  • the synergistic effect of the agent according to the invention consists in a considerable improvement in the handle, which is largely retained even after several delicates.
  • the sewability of the treated textiles is improved in a particularly surprising manner. This is shown by a considerable reduction in the needle insertion force.
  • the number of stitch explosive damage when sewing is reduced.
  • the volume resistance as a measure of the electrostatic equipment is improved.
  • the textile products finished with the agent according to the invention are free from stains. A complete bath extraction takes place during treatment in the dyeing machine.
  • the agents according to the invention can additionally contain further preparation agents in each effective amount.
  • additional preparation agents are crease-free resins with the acid catalysts required for this, optical brighteners, fillers.
  • the modified organopolysiloxanes A and B can be distributed in water without the addition of non-systemic emulsifiers, resulting in clear to slightly cloudy, colloidal solutions. These aqueous preparations are independent of the concentration, i.e. they are stable in the form of stock solutions or in the form of solutions diluted for use and do not separate even after prolonged storage.
  • Organopolysiloxanes of this structure are known from the prior art. They can be prepared by adding the polyoxyalkylene ether of allyl alcohol to the corresponding hydrogen siloxane in the presence of catalysts, in particular platinum catalysts stores. If up to 10 mol% of the radicals R 3 are to be longer-chain alkyl radicals, these can be introduced by adding an appropriate olefin to SiH groups of the hydrogen siloxane. The preparation of such compounds is described, for example, in EU-OS 0 125 779.
  • the agent according to the invention contains as organopolysiloxane B a polymer with optionally essentially repeating units of the general average formula in which R7, X ⁇ are as defined above, R 12 is a divalent hydrocarbon radical with at least 2 carbon atoms, which have a hydroxyl group and whose carbon chain can be interrupted by an oxygen or nitrogen atom, q has a value from 20 to 200 and s ⁇ 1.
  • agents which only contain the organopolysiloxane A are compared with agents according to the invention which contain the organopolysiloxanes A and B together and the synergistic effect is demonstrated.
  • the aqueous preparations are obtained by simply incorporating water into the modified organpolysiloxanes A or A and B with high shear force.
  • the preparation 3 consists of a 30% by weight aqueous solution of a mixture of the organopolysiloxanes A and B in a weight ratio of 4: 1, the residues and indices in the general formula I of the polymer A.
  • Mean Cl ⁇ .
  • the preparation 4 consists of a 30% by weight aqueous solution of a mixture of the organopolysiloxanes A and B in a weight ratio of 6: 1, the residues and indices in the general formula I of the polymer A.
  • the preparation 5 consists of a 30% by weight aqueous solution of a mixture of the organopolysiloxanes A and B in a weight ratio of 2: 1, with the residues and indices in the general formula I of the polymer A.
  • R1 -CH3,
  • R2 - (CH2) 3-O- (C2H4O) x - (C3H6O) y -H
  • R3 -CH3 mean and in the general formula III of polymer B the residues and indices
  • R12 - (CH2) 6-
  • X ⁇ H3C-COO ⁇ mean.
  • the preparation 6 consists of an aqueous emulsion containing 15% by weight of a dimethylpolysiloxane with a viscosity of 10,000 mm2 101. s and 15 wt .-% of an organic plasticizer based on a quaternary imidazolinium compound with two longer aliphatic alkyl radicals, each with 18 carbon atoms.
  • a cotton / polyester knitted fabric (35/65) made from open-end spun yarns is, after dyeing, in a nozzle dyeing machine with 2% by weight, based on the weight of the goods, of preparations 1 to 6 at a liquor ratio of 1:10 , a pH of 6 ⁇ 0.5 and a temperature of 45 ° C for 20 minutes.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Silicon Polymers (AREA)

Abstract

Agent for finishing textile fibres or products consisting of textile fibres which contains 0.5 to 80% by weight of a mixture of modified organopolysiloxanes A and B in a weight ratio A : B of 10 : 1 to 1 : 1, the organopolysiloxane A being a linear siloxane containing polyether groups and having at least 40 dialkylsiloxy units, to which are bonded at least 2 polyether groups, each having a molecular weight of 600 to 4,000 and consisting of 40 to 100 mol% oxyethylene units, the remainder to 100 mol% being oxypropylene units, and the ratio of the number of dialkylsiloxy units to the number of polyether groups being >/= 8, and the organopolysiloxane B being a linear siloxane containing a quaternary ammonium groups and having at least 20 dialkylsiloxy units, to which siloxane at least 2 quaternary ammonium groups are bonded via carbon, and the ratio of the number of dialkylsiloxy units to the number of quaternary ammonium groups being >/= 10. <??>The agent improves the handle of the finished fibres or fibre products with simultaneous hydrophilisation. This improvement in handle is also achieved in the case of twisted open-end yarns. The finished fibres or fibre products can be readily redyed or overdyed. They have good antielectrostatic properties.

Description

Die Erfindung betrifft ein Mittel zum Ausrüsten von Textilfasern oder aus Textilfasern bestehenden Produkten, wie Geweben, Gewirken oder Vliesen.The invention relates to an agent for finishing textile fibers or products consisting of textile fibers, such as woven, knitted or nonwoven.

Die Erfindung betrifft insbesondere ein Mittel zur hydrophilierenden weichmachenden Ausrüstung von Textilfasern oder aus Textilfasern be­stehenden Produkten auf der Basis von wäßrigen Zubereitungen silicium­organischer Verbindungen.The invention relates in particular to an agent for the hydrophilizing softening of textile fibers or products consisting of textile fibers based on aqueous preparations of organosilicon compounds.

Siliciumorganische Verbindungen werden in beachtlichem Umfang bei der Veredlung von Textilgarnen und Textilien verwendet. Dabei wirken die siliciumorganischen Verbindungen entsprechend ihrer jeweiligen Struk­tur und Modifizierung als Weichmacher, Antischaummittel, Hydrophobie­rungsmittel, Appreturmittel und als Mittel zur Verbesserung des Griffs. Infolge der Möglichkeit, Organosiloxane mit funktionellen or­ganischen Gruppen zu modifizieren, lassen sich die Silicone dem jewei­ligen Verwendungszweck anpassen.Organosilicon compounds are used to a considerable extent in the finishing of textile yarns and textiles. According to their respective structure and modification, the organosilicon compounds act as plasticizers, anti-foaming agents, water repellents, finishing agents and as agents for improving the feel. Due to the possibility of modifying organosiloxanes with functional organic groups, the silicones can be adapted to the respective purpose.

Über die Einsatzmöglichkeiten von Dimethylpolysiloxanen und mit ande­ren organischen Gruppen modifizierten Polysiloxanen gibt es eine um­fangreiche Patentliteratur. Stellvertretend für die Literatur wird auf eine Übersichtsarbeit in der Zeitschrift "Textilveredlung" 20 (1985) 8 bis 12, hingewiesen.There is extensive patent literature on the possible uses of dimethylpolysiloxanes and polysiloxanes modified with other organic groups. Representative of the literature, reference is made to an overview in the magazine "Textilveredlung" 20 (1985) 8 to 12.

Der vorliegenden Erfindung liegt die Aufgabe zugrunde, Mittel zum Aus­rüsten von Textilfasern oder aus Textilfasern bestehenden Produkten zu finden, welche in der Lage sind, den Griff der ausgerüsteten Fasern oder Faserprodukte unter gleichzeitiger Hydrophilierung zu verbessern. Die Griffverbesserung soll auch bei festgedrehten Open-End-Garnen er­zielt werden. Hierzu ist es wichtig, daß die Mittel das textile Ma­terial gut benetzen und in den Faserverband penetrieren, wobei die Be­netzung und Penetration auch beim Ausrüsten von hydrophobem Textilma­terial gewährleistet werden soll. Die Produkte sollen den Textilmate­rialien neben dem guten Griff insbesondere eine gute Hydrophilie ver­mitteln, um zu gewährleisten, daß die ausgerüsteten Textilfasern oder Textilien problemlos um- oder überfärbt werden können und ferner gute antielektrostatische Eigenschaften besitzen.The object of the present invention is to provide means for finishing textile fibers or products consisting of textile fibers find which are able to improve the grip of the finished fibers or fiber products with simultaneous hydrophilization. The improvement in the grip should also be achieved with twisted open-end yarns. For this it is important that the agents wet the textile material well and penetrate into the fiber structure, whereby the wetting and penetration should also be ensured when finishing hydrophobic textile material. In addition to the good feel, the products are said to impart good hydrophilicity to the textile materials, in order to ensure that the finished textile fibers or textiles can be recolored or recolored without problems and also have good anti-electrostatic properties.

Eine weitere Forderung an die gewünschten Ausrüstungsmittel besteht darin, daß sie in Form der wäßrigen Zubereitung hohe Badstabilität aufweisen, d.h. sich auch bei längerer Lagerung und bei der Anwendung, insbesondere bei einer Verdünnung, nicht entmischen und mit anderen üblichen Ausrüstungshilfsmitteln verträglich sind.A further requirement for the desired finishing agents is that they have high bath stability in the form of the aqueous preparation, i.e. do not separate even after prolonged storage and during use, especially when diluted, and are compatible with other conventional finishing aids.

Diese gewünschte Eigenschaftskombination wurde überraschend bei einem Mittel gefunden, welches erfindungsgemäß dadurch gekennzeichnet ist, daß es 0,5 bis 80 Gew.-% eines Gemisches modifizierter Organopolysil­oxane A und B im Gewichtsverhältnis A : B von 10 : 1 bis 1 : 1 ent­hält, wobei das Organopolysiloxan A ein Polyethergruppen enthaltendes lineares Siloxan mit mindestens 40 Dialkylsiloxyeinheiten ist, an wel­ches mindestens 2 Polyethergruppen eines Molgewichtes von jeweils 600 bis 4000, die aus 40 bis 100 Mol-% Oxyethyleneinheiten, Rest auf 100 Mol-% Oxypropyleneinheiten bestehen, gebunden sind, und das Ver­hältnis der Zahl der Dialkylsiloxyeinheiten : Zahl der Polyethergrup­pen ≧ 8 ist, und das Organopolysiloxan B ein quaternäre Ammonium­gruppen enthaltendes lineares Siloxan mit mindestens 20 Dialkylsiloxy­einheiten ist, an welches über Kohlenstoff mindestens 2 quaternäre Ammoniumgruppen gebunden sind, und das Verhältnis der Zahl der Dial­kylsiloxyeinheiten : Zahl der quaternären Ammoniumgruppen ≧ 10 ist.This desired combination of properties was surprisingly found in an agent which is characterized according to the invention in that it contains 0.5 to 80% by weight of a mixture of modified organopolysiloxanes A and B in a weight ratio A: B of 10: 1 to 1: 1, where the organopolysiloxane A is a linear siloxane containing polyether groups and having at least 40 dialkylsiloxy units, to which at least 2 polyether groups with a molecular weight of 600 to 4000 each, which consist of 40 to 100 mol% oxyethylene units, the remainder to 100 mol% oxypropylene units, are bound, and the ratio of the number of dialkylsiloxy units: number of polyether groups ≧ 8, and the organopolysiloxane B is a quaternary ammonium group-containing linear siloxane with at least 20 dialkylsiloxy units to which at least 2 quaternary ammonium groups are bonded via carbon, and the ratio of the number of dialkylsiloxy units: number the quaternary ammonium g ruppen ≧ 10.

Vorzugsweise besteht das Mittel aus
0,5 bis 80 Gew.-% des Organopolysiloxangemisches A, B und
20 bis 99,5 Gew.-% Wasser und/oder einem wassermischbaren organi­schen Lösungsmittel.The agent preferably consists of
0.5 to 80 wt .-% of the organopolysiloxane mixture A, B and
20 to 99.5 wt .-% water and / or a water-miscible organic solvent.

Polyethergruppen enthaltende lineare Polysiloxane sind seit langem be­kannt und werden auch für Zwecke der Textilveredlung, zur Verbesserung des Griffs und als Netzmittel verwendet. Aus dem Stand der Technik sind auch siliciumorganische Verbindungen mit quaternären Ammonium­gruppen bekannt, welche insbesondere zur Verringerung der statischen Aufladung von Textilien eingesetzt werden.Linear polysiloxanes containing polyether groups have been known for a long time and are also used for textile finishing purposes, to improve the feel and as a wetting agent. Organosilicon compounds with quaternary ammonium groups are also known from the prior art, which are used in particular to reduce the static charge on textiles.

Es hat sich jedoch in unerwarteter Weise gezeigt, daß die Gemische der oben definierten Organopolysiloxane A (Polyethergruppen enthaltende lineare Siloxane) und Organopolysiloxane B (quaternäre Ammoniumgruppen enthaltende lineare Siloxane) Eigenschaften aufweisen, die in diesem Maße bei den beiden Komponenten A und B jeweils für sich genommen nicht gefunden werden können. Dieser synergistische Effekt war auch unter Berücksichtigung des Standes der Technik nicht zu erwarten.However, it has been shown, unexpectedly, that the mixtures of the organopolysiloxanes A defined above (linear siloxanes containing polyether groups) and organopolysiloxanes B (linear siloxanes containing quaternary ammonium groups) have properties which, to this extent, are the same for the two components A and B. taken cannot be found. This synergistic effect was not to be expected even when considering the state of the art.

Wie in den Beispielen näher belegt, besteht der synergistische Effekt des erfindungsgemäßen Mittels in einer erheblichen Verbesserung des Griffes, welche auch nach mehreren Feinwäschen weitgehend erhalten bleibt. In besonders überraschender Weise wird die Vernähbarkeit der behandelten Textilien verbessert. Dies zeigt sich in einer erheblichen Reduzierung der Nadeleinstichkraft. Die Zahl der Maschensprengschäden beim Vernähen wird verringert. Der Durchgangswiderstand als Maß für die elektrostatische Ausrüstung wird verbessert. Die mit dem erfin­dungsgemäßen Mittel ausgerüsteten Textilprodukte sind frei von Flek­ken. Bei der Behandlung im Färbeapparat findet ein vollständiger Bad­auszug statt.As demonstrated in the examples, the synergistic effect of the agent according to the invention consists in a considerable improvement in the handle, which is largely retained even after several delicates. The sewability of the treated textiles is improved in a particularly surprising manner. This is shown by a considerable reduction in the needle insertion force. The number of stitch explosive damage when sewing is reduced. The volume resistance as a measure of the electrostatic equipment is improved. The textile products finished with the agent according to the invention are free from stains. A complete bath extraction takes place during treatment in the dyeing machine.

Die erfindungsgemäßen Mittel können weitere Präparationsmittel in je­weils wirksamer Menge zusätzlich enthalten. Beispiele solcher üblichen Präparationsmittel sind Knitterfreiharze mit den dazu notwendigen sauren Katalysatoren, optische Aufheller, Füllmittel.The agents according to the invention can additionally contain further preparation agents in each effective amount. Examples of such customary preparation agents are crease-free resins with the acid catalysts required for this, optical brighteners, fillers.

Die modifizierten Organopolysiloxane A und B lassen sich ohne Zusatz systemfremder Emulgatoren in Wasser verteilen, wobei klare bis schwach trübe, kolloidale Lösungen entstehen. Diese wäßrigen Zubereitungen sind unabhängig von der Konzentration, d.h. sie sind in Form von Stammlösungen oder in Form von für die Anwendung verdünnten Lösungen stabil und entmischen sich auch bei längerer Lagerung nicht.The modified organopolysiloxanes A and B can be distributed in water without the addition of non-systemic emulsifiers, resulting in clear to slightly cloudy, colloidal solutions. These aqueous preparations are independent of the concentration, i.e. they are stable in the form of stock solutions or in the form of solutions diluted for use and do not separate even after prolonged storage.

Entsprechend einer bevorzugten Ausführungsform der Erfindung enthält das erfindungsgemäße Mittel als Organopolysiloxan A ein Polymeres der allgemeinen durchschnittlichen Formel

Figure imgb0001
wobei
R¹ im Molekül gleich oder verschieden ist und einen Methyl- oder R²-Rest bedeutet,
R² die Gruppe -(CH₂)₃O(C₂H₄O)x(C₃H₆O)yR⁴ ist,
R⁴ = Wasserstoff-, Alkylrest mit 1 bis 4 C-Atomen oder Acylrest,
x = 10 bis 50 und
y = 0 bis 40 ist,
mit der Maßgabe, daß das mittlere Molekulargewicht der Gruppen R² 600 bis 4000 beträgt,
R³ im Molekül gleich oder verschieden ist und einen Alkylrest mit 1 bis 20 C-Atomen bedeutet, wobei aber mindestens 90 Mol-% der Reste R³ Methylreste sein müssen,
n einen Wert von 40 bis 200,
m einen Wert von 0 bis 20 hat, mit der Maßgabe, daß, wenn m = 0 ist,
R¹ = R² ist, und, wenn m > 0 ist, der Quotient n : m ≧ 8 ist.According to a preferred embodiment of the invention, the agent according to the invention contains as organopolysiloxane A a polymer of the general average formula
Figure imgb0001
 in which
R¹ is the same or different in the molecule and represents a methyl or R² radical,
R² is the group - (CH₂) ₃O (C₂H₄O) x (C₃H₆O) y R⁴,
R⁴ = hydrogen, alkyl radical with 1 to 4 carbon atoms or acyl radical,
x = 10 to 50 and
y = 0 to 40,
with the proviso that the average molecular weight of the groups R² is 600 to 4000,
R³ is the same or different in the molecule and means an alkyl radical with 1 to 20 C atoms, but at least 90 mol% of the radicals R³ must be methyl radicals,
n a value from 40 to 200,
m has a value from 0 to 20, with the proviso that if m = 0,
R¹ = R² and, if m> 0, the quotient n: m ≧ 8.

Organopolysiloxane dieser Struktur sind aus dem Stand der Technik be­kannt. Ihre Herstellung kann dadurch erfolgen, daß man den Polyoxyal­kylenether des Allylalkohols an das entsprechende Wasserstoffsiloxan in Gegenwart von Katalysatoren, insbesondere Platinkatalysatoren, an­ lagert. Falls bis zu 10 Mol-% der Reste R³ längerkettige Alkylreste sein sollen, können diese durch Anlagerung eines entsprechenden Ole­fins an SiH-Gruppen des Wasserstoffsiloxans eingeführt werden. Die Herstellung solcher Verbindungen ist z.B. in der EU-OS 0 125 779 be­schrieben.Organopolysiloxanes of this structure are known from the prior art. They can be prepared by adding the polyoxyalkylene ether of allyl alcohol to the corresponding hydrogen siloxane in the presence of catalysts, in particular platinum catalysts stores. If up to 10 mol% of the radicals R 3 are to be longer-chain alkyl radicals, these can be introduced by adding an appropriate olefin to SiH groups of the hydrogen siloxane. The preparation of such compounds is described, for example, in EU-OS 0 125 779.

Als Organopolysiloxan B enthält das erfindungsgemäße Mittel vorzugs­weise ein Polymeres der allgemeinen durchschnittlichen Formel

Figure imgb0002
wobei
R³ wie oben definiert ist,
R⁵ im Molekül gleich oder verschieden ist und einen Methyl- oder R⁶-Rest bedeutet,
Figure imgb0003
 R⁷ = zweiwertiger Kohlenwasserstoffrest, dessen Kohlenstoffkette durch ein Sauerstoffatom unterbrochen sein kann,
R⁸, R⁹, R¹⁰ = im Molekül und der Gruppe gleich oder verschie­den, Alkylreste mit jeweils 1 bis 18 C-Atomen, wobei einer der Reste R⁸, R⁹, R¹⁰ je Gruppe der Rest
-(CH₂)₃NHCOR¹¹, R¹¹ = Alkylrest mit 7 bis 17 C-Ato­men, sein kann,
X ⊖ = ein beliebiges einwertiges Anion,
o einen Wert von 20 bis 200,
p einen Wert von 0 bis 20 hat, mit der Maßgabe, daß, wenn p = 0 ist, R⁵ = R⁶ ist, und, wenn p > 0 ist, der Quotient o : p ≧ 10 ist.As organopolysiloxane B, the agent according to the invention preferably contains a polymer of the general average formula
Figure imgb0002
 in which
R³ is as defined above,
R⁵ is the same or different in the molecule and represents a methyl or R⁶ radical,
Figure imgb0003
 R⁷ = divalent hydrocarbon radical, the carbon chain of which can be interrupted by an oxygen atom,
R⁸, R⁹, R¹⁰ = in the molecule and the group the same or different, alkyl radicals each having 1 to 18 carbon atoms, one of the radicals R⁸, R⁹, R¹⁰ per group the rest
- (CH₂) ₃NHCOR¹¹, R¹¹ = alkyl radical having 7 to 17 carbon atoms,
X ⊖ = any monovalent anion,
o a value from 20 to 200,
p has a value from 0 to 20, with the proviso that if p = 0, R⁵ = R⁶ and, if p> 0, the quotient o: p ≧ 10.

Beispiele für den Rest R⁷ sind

Figure imgb0004
Examples of the rest R⁷ are
Figure imgb0004

Verbindungen dieser Art und ihre Herstellung sind in der DE-OS .. .. ... (Patentanmeldung P 37 19 086.5-44) und der US-PS 3 389 160 beschrieben. Dabei kann die Herstellung in der Weise erfol­gen, daß man ein entsprechendes Epoxidgruppen aufweisendes Organopoly­siloxan mit tertiären Aminen in solchen Mengenverhältnissen umsetzt, daß jeder Epoxidgruppe mindestens eine tertiäre Aminogruppe entspricht und man die Umsetzung in Gegenwart eines Säureäquivalentes, bezogen auf zu quaternierendes Stickstoffatom, bei erhöhten Temperaturen durchführt.Compounds of this type and their preparation are described in DE-OS .. .. ... (patent application P 37 19 086.5-44) and US Pat. No. 3,389,160. The preparation can be carried out by reacting a corresponding organopolysiloxane containing epoxy groups with tertiary amines in proportions such that at least one tertiary amino group corresponds to each epoxy group and reacting in the presence of an acid equivalent, based on the nitrogen atom to be quaternized, at elevated temperatures carries out.

In einer anderen bevorzugten Ausführungsform enthält das erfindungsge­mäße Mittel als Organopolysiloxan B ein Polymeres mit gegebenenfalls im wesentlichen sich wiederholenden Einheiten der allgemeinen durch­schnittlichen Formel

Figure imgb0005
wobei
R⁷, X⊖ wie oben definiert sind,
R¹² ein zweiwertiger Kohlenwasserstoffrest mit mindestens 2 C-Atomen, der eine Hydroxylgruppe aufweisen und dessen Koh­lenstoffkette durch ein Sauerstoff- oder Stickstoffatom unter­brochen sein kann, ist,
q einen Wert von 20 bis 200 hat und
s ≧ 1 ist.In another preferred embodiment, the agent according to the invention contains as organopolysiloxane B a polymer with optionally essentially repeating units of the general average formula
Figure imgb0005
 in which
R⁷, X ⊖ are as defined above,
R 12 is a divalent hydrocarbon radical with at least 2 carbon atoms, which have a hydroxyl group and whose carbon chain can be interrupted by an oxygen or nitrogen atom,
q has a value from 20 to 200 and
s ≧ 1.

Beispiele für den Substituenten R¹² sind

Figure imgb0006
Examples of the substituent R¹² are
Figure imgb0006

Verbindungen dieser Art sind in der DE-OS .. .. ... (Patentanmeldung P 37 05 121.0-44) beschrieben. Entsprechend dem dort näher erläuterten Herstellungsverfahren werden zunächst α,ω-Wasserstoffpolysiloxane mit, bezogen auf SiH-Gruppen, äquimolaren Mengen eines Epoxids, welches endständig eine olefinische Bindung hat, in Gegenwart eines Hydrosily­lierungskatalysators in an sich bekannter Weise umgesetzt, wonach das so erhaltene Reaktionsprodukt mit einem ditertiären Amin in Gegenwart von 2 Moläquivalenten Säure, bezogen auf Diamin, bei erhöhten Tempera­turen in solchen Mengen umgesetzt wird, daß jeder Epoxidgruppe eine tertiäre Aminogruppe entspricht.Compounds of this type are described in DE-OS .. .. ... (patent application P 37 05 121.0-44). According to the production process explained in more detail there, α, ω-hydrogen polysiloxanes are first reacted in a manner known per se in the presence of a hydrosilylation catalyst, based on SiH groups, with equimolar amounts of an epoxide which has an olefinic bond, after which the reaction product thus obtained is also used a ditertiary amine in the presence of 2 molar equivalents of acid, based on diamine, is reacted at elevated temperatures in amounts such that each epoxy group corresponds to a tertiary amino group.

Beispiele erfindungsgemäß einsetzbarer Siloxane:

Figure imgb0007

  • A 1 R¹ = R³ = CH₃ ;
    R² = -(CH₂)₃-O-(C₂H₄O)₃₀-H ;
    n = 50, m = 5
  • A 2 R¹ = R² = -(CH₂)₃-O-(C₂H₄O)₂₀-(C₃H₆O)₅-H ;
    R³ = CH₃ ;
    n = 150, m = 10
  • A 3 R¹ = CH₃ ;
    R² = -(CH₂)₃-O-(C₂H₄O)₃₅-H ;
    R³ = 5 Mol-% C₁₆H₃₃ und 95 Mol-% CH₃ ;
    n = 125, m = 15
  • A 4 R¹ = R² = -(CH₂)₃-O-(C₂H₄O)₂₀-(C₃H₆O)₂-CH₃ ;
    R³ = CH₃ ;
    n = 55, m = 0
  • A 5 R¹ = R³ = CH₃ ;

    R² = -(CH₂)₃-O-(C₂H₄O)₄₀-
    Figure imgb0008
    -CH₃ ;
    n = 200, m = 10
Figure imgb0009
Figure imgb0010
Figure imgb0011
 Examples of siloxanes which can be used according to the invention:
Figure imgb0007
  • A 1 R¹ = R³ = CH₃;
    R² = - (CH₂) ₃-O- (C₂H₄O) ₃₀-H;
    n = 50, m = 5
  • A 2 R¹ = R² = - (CH₂) ₃-O- (C₂H₄O) ₂₀- (C₃H₆O) ₅-H;
    R³ = CH₃;
    n = 150, m = 10
  • A 3 R¹ = CH₃;
    R² = - (CH₂) ₃-O- (C₂H₄O) ₃₅-H;
    R³ = 5 mole% C₁₆H₃₃ and 95 mole% CH₃;
    n = 125, m = 15
  • A 4 R¹ = R² = - (CH₂) ₃-O- (C₂H₄O) ₂₀- (C₃H₆O) ₂-CH₃;
    R³ = CH₃;
    n = 55, m = 0
  • A 5 R¹ = R³ = CH₃;

    R² = - (CH₂) ₃-O- (C₂H₄O) ₄₀-
    Figure imgb0008
    -CH₃;
    n = 200, m = 10
Figure imgb0009
Figure imgb0010
Figure imgb0011

Beispiele erfindungsgemäßer Mittel (Angaben in Gew.-%):Examples of agents according to the invention (data in% by weight):

  • 1. 20 % Siloxan A 1
    5 % Siloxan B 3
    30 % 1,2-Propylenglykol
    45 % Wasser    1. 20% siloxane A 1
    5% siloxane B 3
    30% 1,2-propylene glycol
    45% water
  • 2. 10 % Siloxan A 1
    10 % Siloxan A 4
    10 % Siloxan B 1
    70 % Wasser    2. 10% siloxane A 1
    10% siloxane A 4
    10% siloxane B 1
    70% water
  • 3. 60 % Siloxan A 4
    6 % Siloxan B 2
    34 % 1,2-Propylenglykol    3. 60% siloxane A 4
    6% siloxane B 2
    34% 1,2-propylene glycol
  • 4. 5 % Siloxan A 2
    5 % Siloxan B 5
    90 % Wasser    4. 5% siloxane A 2
    5% siloxane B 5
    90% water
  • 5. 20 % Siloxan A 5
    10 % Siloxan B 4
    5 % Siloxan B 6
    30 % i-Propanol
    35 % Wasser    5. 20% siloxane A 5
    10% siloxane B 4
    5% siloxane B 6
    30% i-propanol
    35% water
  • 6. 2 % Siloxan A 3
    2 % Siloxan B 6
    96 % Wasser    6. 2% siloxane A 3
    2% siloxane B 6
    96% water
  • 7. 10 % Siloxan A 4
    5 % Siloxan B 7
    85 % Wasser    7. 10% siloxane A 4
    5% siloxane B 7
    85% water

In den folgenden Beispielen werden die Eigenschaften von Mitteln, wel­che nur das Organopolysiloxan A enthalten, mit erfindungsgemäßen Mit­teln, welche die Organopolysiloxane A und B gemeinsam enthalten, ver­glichen und der synergistische Effekt nachgewiesen. Die wäßrigen Zu­bereitungen werden dabei durch einfaches, scherkraftreiches Einarbei­ten von Wasser in die modifizierten Organpolysiloxane A bzw. A und B erhalten.In the following examples the properties of agents which only contain the organopolysiloxane A are compared with agents according to the invention which contain the organopolysiloxanes A and B together and the synergistic effect is demonstrated. The aqueous preparations are obtained by simply incorporating water into the modified organpolysiloxanes A or A and B with high shear force.

Beispiel 1example 1 (nicht erfindungsgemäß)(not according to the invention)

Die Zubereitung 1 besteht aus einer 30 gew.-%igen wäßrigen Lösung des Organopolysiloxans A, wobei die Reste und Indices in der allgemeinen Formel I folgende Bedeutung haben:
n = 20,
m = 5,
R¹ = -CH₃,
R² = -(CH₂)₃-O-(C₂H₄O)x-(C₃H₆O)y-H ,
x = 11,
y = 3,
R³ = -CH₃.Preparation 1 consists of a 30% by weight aqueous solution of organopolysiloxane A, the radicals and indices in general formula I having the following meanings:
n = 20,
m = 5,
R¹ = -CH₃,
R² = - (CH₂) ₃-O- (C₂H₄O) x - (C₃H₆O) y -H,
x = 11,
y = 3,
R³ = -CH₃.

Beispiel 2Example 2 (nicht erfindungsgemäß)(not according to the invention)

Die Zubereitung 2 besteht aus einer 30 gew.-%igen wäßrigen Lösung des Organopolysiloxans A, wobei die Reste und Indices in der allgemeinen Formel 1 folgende Bedeutung haben:
n = 75,
m = 5,
R¹ = -CH₃,
R² = -(CH₂)₃-O-(C₂H₄O)x-(C₃H₆O)y-H,
x = 20,
y = 5,
R³ = -CH₃.Preparation 2 consists of a 30% by weight aqueous solution of organopolysiloxane A, the radicals and indices in general formula 1 having the following meanings:
n = 75,
m = 5,
R¹ = -CH₃,
R² = - (CH₂) ₃-O- (C₂H₄O) x - (C₃H₆O) y -H,
x = 20,
y = 5,
R³ = -CH₃.

Beispiel 3Example 3 (erfindungsgemäß)(according to the invention)

Die Zubereitung 3 besteht aus einer 30 gew.-%igen wäßrigen Lösung eines Gemisches der Organopolysiloxane A und B im Gewichtsverhältnis von 4 : 1, wobei in der allgemeinen Formel I des Polymers A die Reste und Indices
n = 75,
m = 5,
R¹ = -CH₃,
R² = -(CH₂)₃-O-(C₂H₄O)x-(C₃H₆O)y-H ,
x = 20,
y = 5,
R³ = -CH₃ bedeuten
und in der allgemeinen Formel II des Polymers B die Reste und Indices
R³ = -CH₃,
o = 80,
p = 5,
R⁵ = -CH₃,

R⁶ = -(CH₂)₃-O-CH₂-

Figure imgb0012
-CH₂-N⊕ (CH₃)₃ . Cl⊖ bedeuten.The preparation 3 consists of a 30% by weight aqueous solution of a mixture of the organopolysiloxanes A and B in a weight ratio of 4: 1, the residues and indices in the general formula I of the polymer A.
n = 75,
m = 5,
R¹ = -CH₃,
R² = - (CH₂) ₃-O- (C₂H₄O) x - (C₃H₆O) y -H,
x = 20,
y = 5,
R³ = -CH₃ mean
and in the general formula II of polymer B the residues and indices
R³ = -CH₃,
o = 80,
p = 5,
R⁵ = -CH₃,

R⁶ = - (CH₂) ₃-O-CH₂-
Figure imgb0012
-CH₂-N ⊕ (CH₃) ₃. Mean Cl ⊖ .

Beispiel 4Example 4 (erfindungsgemäß)(according to the invention)

Die Zubereitung 4 besteht aus einer 30 gew.-%igen wäßrigen Lösung eines Gemisches der Organopolysiloxane A und B im Gewichtsverhältnis von 6 : 1, wobei in der allgemeinen Formel I des Polymers A die Reste und Indices
n = 75,
m = 5,
R¹ = -CH₃,
R² = -(CH₂)₃-O-(C₂H₄O)x-(C₃H₆O)y-H ,
x = 20,
y = 5,
R³ = -CH₃ bedeuten
und in der allgemeinen Formel II des Polymers B die Reste und Indices
R³ = -CH₃,
o = 30,
p = 0,
R⁵ = R⁶,

Figure imgb0013
bedeuten.The preparation 4 consists of a 30% by weight aqueous solution of a mixture of the organopolysiloxanes A and B in a weight ratio of 6: 1, the residues and indices in the general formula I of the polymer A.
n = 75,
m = 5,
R¹ = -CH₃,
R² = - (CH₂) ₃-O- (C₂H₄O) x - (C₃H₆O) y -H,
x = 20,
y = 5,
R³ = -CH₃ mean
and in the general formula II of polymer B the residues and indices
R³ = -CH₃,
o = 30,
p = 0,
R⁵ = R⁶,
Figure imgb0013
 mean.

Beispiel 5Example 5 (erfindungsgemäß)(according to the invention)

Die Zubereitung 5 besteht aus einer 30 gew.-%igen wäßrigen Lösung eines Gemisches der Organopolysiloxane A und B im Gewichtsverhältnis von 2 : 1, wobei in der allgemeinen Formel I des Polymers A die Reste und Indices
n = 90,
m = 6,
R¹ = -CH₃,
R² = -(CH₂)₃-O-(C₂H₄O)x-(C₃H₆O)y-H ,
x = 30,
y = 0,
R³ = -CH₃ bedeuten
und in der allgemeinen Formel III des Polymers B die Reste und Indices
R⁷ = -(CH₂)₃-O-CH₂-

Figure imgb0014
-CH₂-,

q = 25,
s > 1,
R¹² = -(CH₂)₆- ,
X⊖ = H₃C-COO⊖ bedeuten.The preparation 5 consists of a 30% by weight aqueous solution of a mixture of the organopolysiloxanes A and B in a weight ratio of 2: 1, with the residues and indices in the general formula I of the polymer A.
n = 90,
m = 6,
R¹ = -CH₃,
R² = - (CH₂) ₃-O- (C₂H₄O) x - (C₃H₆O) y -H,
x = 30,
y = 0,
R³ = -CH₃ mean
and in the general formula III of polymer B the residues and indices
R⁷ = - (CH₂) ₃-O-CH₂-
Figure imgb0014
-CH₂-,

q = 25,
s> 1,
R¹² = - (CH₂) ₆-,
X ⊖ = H₃C-COO ⊖ mean.

Beispiel 6Example 6 (nicht erfindungsgemäß)(not according to the invention)

Die Zubereitung 6 besteht aus einer wäßrigen Emulsion mit einem Gehalt von 15 Gew.-% eines Dimethylpolysiloxans mit einer Viskosität von 10 000 mm²⁻¹ . s und 15 Gew.-% eines organischen Weichmachers auf der Basis einer quaternären Imidazoliniumverbindung mit zwei längeren aliphatischen Alkylresten mit jeweils 18 C-Atomen.The preparation 6 consists of an aqueous emulsion containing 15% by weight of a dimethylpolysiloxane with a viscosity of 10,000 mm² 10¹. s and 15 wt .-% of an organic plasticizer based on a quaternary imidazolinium compound with two longer aliphatic alkyl radicals, each with 18 carbon atoms.

Anwendungstechnische Prüfung der Zubereitungen 1 bis 6Application testing of preparations 1 to 6

Ein Baumwoll/Polyester-Gewirke (35/65) aus Open-End-gesponnenen Garnen wird nach dem Färben in einem Düsenfärbeapparat mit jeweils 2 Gew.-%, bezogen auf das Warengewicht, der Zubereitungen 1 bis 6 bei einem Flottenverhältnis von 1 : 10, einem pH-Wert von 6 ± 0,5 und einer Temperatur von 45°C 20 Minuten lang behandelt.A cotton / polyester knitted fabric (35/65) made from open-end spun yarns is, after dyeing, in a nozzle dyeing machine with 2% by weight, based on the weight of the goods, of preparations 1 to 6 at a liquor ratio of 1:10 , a pH of 6 ± 0.5 and a temperature of 45 ° C for 20 minutes.

Nach dem Trocknen unter praxisüblichen Bedingungen wird der Artikel konditioniert und textiltechnisch geprüft. Die erzielten Resultate sind in der folgenden Tabelle aufgeführt.

Figure imgb0015
Figure imgb0016
 After drying under normal conditions, the article is conditioned and checked using textile technology. The results obtained are shown in the following table.
Figure imgb0015
Figure imgb0016

Claims (6)

1. Mittel zum Ausrüsten von Textilfasern oder aus Textilfasern beste­henden Produkten, dadurch gekennzeichnet, daß es 0,5 bis 80 Gew.-% eines Gemisches modifizierter Organopolysiloxane A und B im Ge­wichtsverhältnis A : B von 10 : 1 bis 1 : 1 enthält, wobei das 0r­ganopolysiloxan A ein Polyethergruppen enthaltendes lineares Sil­oxan mit mindestens 40 Dialkylsiloxyeinheiten ist, an welches min­destens 2 Polyethergruppen eines Molgewichtes von jeweils 600 bis 4000, die aus 40 bis 100 Mol-% Oxyethyleneinheiten, Rest auf 100 Mol-% Oxypropyleneinheiten bestehen, gebunden sind, und das Verhältnis der Zahl der Dialkylsiloxyeinheiten : Zahl der Poly­ethergruppen ≧ 8 ist, und das Organopolysiloxan B ein quater­näre Ammoniumgruppen enthaltendes lineares Siloxan mit mindestens 20 Dialkylsiloxyeinheiten ist, an welches über Kohlenstoff minde­stens 2 quaternäre Ammoniumgruppen gebunden sind, und das Verhält­nis der Zahl der Dialkylsiloxyeinheiten : Zahl der quaternären Ammoniumgruppen ≧ 10 ist.1. Means for finishing textile fibers or products consisting of textile fibers, characterized in that it contains 0.5 to 80 wt .-% of a mixture of modified organopolysiloxanes A and B in the weight ratio A: B of 10: 1 to 1: 1, wherein the organopolysiloxane A is a linear siloxane containing polyether groups and having at least 40 dialkylsiloxy units to which at least 2 polyether groups with a molecular weight of 600 to 4000 each, which consist of 40 to 100 mol% oxyethylene units, the remainder to 100 mol% oxypropylene units, are bound, and the ratio of the number of dialkylsiloxy units: number of polyether groups ≧ 8, and the organopolysiloxane B is a quaternary ammonium group-containing linear siloxane with at least 20 dialkylsiloxy units to which at least 2 quaternary ammonium groups are bonded via carbon, and the ratio of the number of dialkylsiloxy units: number of the quaternary ammonium groups is ≧ 10. 2. Mittel nach Anspruch 1, dadurch gekennzeichnet, daß es aus
0,5 bis 80 Gew.-% des Organopolysiloxangemisches A, B und
20 bis 99,5 Gew.-% Wasser und/oder einem wassermischbaren orga­nischen Lösungsmittel besteht.2. Composition according to claim 1, characterized in that it consists of
0.5 to 80 wt .-% of the organopolysiloxane mixture A, B and
20 to 99.5 wt .-% water and / or a water-miscible organic solvent. 3. Mittel nach Anspruch 2, dadurch gekennzeichnet, daß es weitere üb­liche Präparationsmittel in jeweils wirksamer Menge enthält.3. Composition according to claim 2, characterized in that it contains other conventional preparation agents in each effective amount. 4. Mittel nach einem oder mehreren der vorhergehenden Ansprüche, da­durch gekennzeichnet, daß es als Organopolysiloxan A ein Polymeres der allgemeinen durchschnittlichen Formel
Figure imgb0017
 enthält, wobei
R¹ im Molekül gleich oder verschieden ist und einen Methyl- oder R²-Rest bedeutet,
R² die Gruppe -(CH₂)₃O(C₂H₄O)x(C₃H₆O)yR⁴ ist,
R⁴ = Wasserstoff-, Alkylrest mit 1 bis 4 C-Atomen oder Acyl­rest,
x = 10 bis 50 und
y = 0 bis 40 ist,
mit der Maßgabe, daß das mittlere Molekulargewicht der Gruppen R² 600 bis 4000 beträgt,
R³ im Molekül gleich oder verschieden ist und einen Alkylrest mit 1 bis 20 C-Atomen bedeutet, wobei aber mindestens 90 Mol-% der Reste R³ Methylreste sein müssen,
n einen Wert von 40 bis 200,
m einen Wert von 0 bis 20 hat, mit der Maßgabe, daß, wenn m = 0 ist, R¹ = R² ist, und, wenn m > 0 ist, der Quotient n : m ≧ 8 ist.4. Composition according to one or more of the preceding claims, characterized in that it is a polymer of the general average formula as organopolysiloxane A.
Figure imgb0017
 contains, where
R¹ is the same or different in the molecule and represents a methyl or R² radical,
R² is the group - (CH₂) ₃O (C₂H₄O) x (C₃H₆O) y R⁴,
R⁴ = hydrogen, alkyl radical with 1 to 4 carbon atoms or acyl radical,
x = 10 to 50 and
y = 0 to 40,
with the proviso that the average molecular weight of the groups R² is 600 to 4000,
R³ is the same or different in the molecule and means an alkyl radical with 1 to 20 C atoms, but at least 90 mol% of the radicals R³ must be methyl radicals,
n a value from 40 to 200,
m has a value from 0 to 20, with the proviso that if m = 0, R¹ = R² and, if m> 0, the quotient n: m ≧ 8. 5. Mittel nach einem oder mehreren der Ansprüche 1, 2 oder 3, dadurch gekennzeichnet, daß es als Organopolysiloxan B ein Polymeres der allgemeinen durchschnittlichen Formel
Figure imgb0018
 enthält, wobei
R³ wie oben definiert ist,
R⁵ im Molekül gleich oder verschieden ist und einen Methyl- oder R⁶-Rest bedeutet,
Figure imgb0019
 R⁷ = zweiwertiger Kohlenwasserstoffrest, dessen Kohlenstoff­kette durch ein Sauerstoffatom unterbrochen sein kann,
R⁸, R⁹, R¹⁰ = im Molekül und der Gruppe gleich oder ver­schieden, Alkylreste mit jeweils 1 bis 18 C-Atomen, wobei einer der Reste R⁸, R⁹, R¹⁰ je Gruppe der Rest -(CH₂)₃NHCOR¹¹, R¹¹ = Alkylrest mit 7 bis 17 C-Atomen, sein kann,
X⊖ = ein beliebiges einwertiges Anion,
o einen Wert von 20 bis 200,
p einen Wert von 0 bis 20 hat, mit der Maßgabe, daß, wenn p = 0 ist, R⁵ - R⁶ ist, und, wenn p > 0 ist, der Quotient o : p ≧ 10 ist.5. Composition according to one or more of claims 1, 2 or 3, characterized in that it is a polymer of the general average formula as organopolysiloxane B.
Figure imgb0018
 contains, where
R³ is as defined above,
R⁵ is the same or different in the molecule and represents a methyl or R⁶ radical,
Figure imgb0019
 R⁷ = divalent hydrocarbon radical, the carbon chain of which can be interrupted by an oxygen atom,
R⁸, R⁹, R¹⁰ = in the molecule and the group the same or different, alkyl radicals each having 1 to 18 carbon atoms, one of the radicals R⁸, R⁹, R¹⁰ per group the radical - (CH₂) ₃NHCOR¹¹, R¹¹ = alkyl radical with 7 to 17 carbon atoms, can be
X ⊖ = any monovalent anion,
o a value from 20 to 200,
p has a value from 0 to 20, with the proviso that if p = 0, R⁵ - R⁶ and, if p> 0, the quotient o: p ≧ 10. 6. Mittel nach einem oder mehreren der Ansprüche 1, 2 oder 3, dadurch gekennzeichnet, daß es als Organopolysiloxan B ein Polymeres mit gegebenenfalls im wesentlichen sich wiederholenden Einheiten der allgemeinen durchschnittlichen Formel
Figure imgb0020
 enthält, wobei
R⁷, X⊖ wie oben definiert sind,
R¹² ein zweiwertiger Kohlenwasserstoffrest mit mindestens 2 C-Atomen, der eine Hydroxylgruppe aufweisen und dessen Kohlenstoffkette durch ein Sauerstoff- oder Stickstoffatom unterbrochen sein kann, ist,
q einen Wert von 20 bis 200 hat und
s ≧ 1 ist.6. Composition according to one or more of claims 1, 2 or 3, characterized in that it as organopolysiloxane B is a polymer with optionally essentially repeating units of the general average formula
Figure imgb0020
 contains, where
R⁷, X⊖ are as defined above,
R 12 is a divalent hydrocarbon radical with at least 2 carbon atoms, which have a hydroxyl group and whose carbon chain can be interrupted by an oxygen or nitrogen atom,
q has a value from 20 to 200 and
s ≧ 1.
EP89100606A 1988-01-29 1989-01-14 Finishing composition for textile fibres or for textile products Expired - Lifetime EP0339179B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3802622 1988-01-29
DE3802622A DE3802622A1 (en) 1988-01-29 1988-01-29 MEANS FOR CUTTING TEXTILE FIBER OR TEXTILE FIBER PRODUCTS

Publications (3)

Publication Number Publication Date
EP0339179A2 true EP0339179A2 (en) 1989-11-02
EP0339179A3 EP0339179A3 (en) 1991-09-18
EP0339179B1 EP0339179B1 (en) 1992-11-25

Family

ID=6346223

Family Applications (1)

Application Number Title Priority Date Filing Date
EP89100606A Expired - Lifetime EP0339179B1 (en) 1988-01-29 1989-01-14 Finishing composition for textile fibres or for textile products

Country Status (4)

Country Link
US (1) US4921895A (en)
EP (1) EP0339179B1 (en)
DE (2) DE3802622A1 (en)
ES (1) ES2037287T3 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0839947A2 (en) * 1996-11-04 1998-05-06 Schill &amp; Seilacher GmbH &amp; Co. Composition for the permanent hydrophilic treatment of polyolefines, use of the composition and the fibres treated therewith
WO2002010502A1 (en) * 2000-07-27 2002-02-07 Wacker-Chemie Gmbh Method for saturating threads

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3929757A1 (en) * 1989-09-07 1991-03-14 Sandoz Ag Amino-polysiloxane micro-emulsions useful for textile finishing
DE4100703A1 (en) * 1991-01-11 1992-07-16 Chu Tjoei Ho TEXTILE EQUIPMENT
TW282478B (en) * 1992-06-05 1996-08-01 Comfort Tech Inc
US5354815A (en) * 1992-06-05 1994-10-11 Comfort Technologies Polymers having enhanced hydrophilicity and thermal regulated properties and process of producing the same
KR0137001B1 (en) * 1992-06-29 1998-04-28 제임스 에이치. 코넬 Method for imparting softness with reduced yellowing to a textile using a low amine content, high molecular weight aminopolysiloxane
US5668212A (en) * 1992-10-06 1997-09-16 Shizu Naito Aqueous organosiloxane liquid composition and its use
US6080686A (en) * 1993-01-19 2000-06-27 Th. Goldschmidt Ag Soft cellulosic nonwovens and a method for softening nonwovens
US5408012A (en) * 1993-05-27 1995-04-18 Comfort Technologies, Inc. Polymers having enhanced durable hydrophilicity and durable rewetting properties and process of producing the same
US5811482A (en) * 1996-07-17 1998-09-22 Osi Specialties, Inc. Non-migrating hydrophilic silicone finish for hydrophobic substrates such as nonwovens
DE19711452A1 (en) 1997-03-19 1998-09-24 Sca Hygiene Paper Gmbh Moisture regulator-containing composition for tissue products, process for the production of these products, use of the composition for the treatment of tissue products and tissue products in the form of wetlaid, including TAD or airlaid (non-woven) based on flat carrier materials predominantly containing cellulose fibers
EP1000959B1 (en) * 1998-11-14 2003-04-16 Goldschmidt AG Polyetherquat functional polysiloxanes
DE10066215B4 (en) * 2000-07-27 2007-03-22 Ge Bayer Silicones Gmbh & Co. Kg Production of polyquaternary polysiloxanes, useful as wash-resistant fabric conditioners, comprises reacting hydrogen-terminal dimethylpolysiloxane with olefin-terminal epoxide, and reacting with mixture of tertiary and ditertiary amines
DE10036694A1 (en) * 2000-07-27 2002-02-14 Wacker Chemie Gmbh Process for the treatment of organic fibers with amino-functional organosilicon compounds
US6503412B1 (en) * 2000-08-24 2003-01-07 Kimberly-Clark Worldwide, Inc. Softening composition
DE10050933A1 (en) * 2000-10-13 2002-04-25 Ciba Sc Pfersee Gmbh Flowable non-crosslinked polyorganosiloxane for treatment of fabrics contains at least one quaternary group comprising at least one nitrogen atom, and at least one further polar radical
DE10115476A1 (en) * 2001-03-29 2002-10-10 Wacker Chemie Gmbh Process for the treatment of organic fibers
DE10204517A1 (en) * 2002-02-05 2003-08-07 Ciba Sc Pfersee Gmbh Polysiloxanes with quaternary groups containing nitrogen atoms
DE10221521A1 (en) * 2002-05-14 2003-12-04 Ge Bayer Silicones Gmbh & Co Formulations of silicone softeners for textile finishing
DE102005039398A1 (en) * 2005-08-20 2007-02-22 Goldschmidt Gmbh Process for the preparation of addition products of compounds containing SiH groups to olefin-containing reactants in aqueous media
WO2013148629A1 (en) 2012-03-29 2013-10-03 Momentive Performance Materials Inc. LOW VISCOSITY POLYORGANOSILOXANES COMPRISING QUATERNARY AMMONIUM GROUPS, METHODS FOR THE PRODUCTION AND THE USE THEREOF (ll)
EP3199592B1 (en) 2012-03-29 2020-02-26 Momentive Performance Materials GmbH Low viscosity polyorganosiloxanes comprising quaternary ammonium groups, methods for the production and the use thereof
US9198849B2 (en) 2013-07-03 2015-12-01 The Procter & Gamble Company Shampoo composition comprising low viscosity emulsified silicone polymers
DE102013219046A1 (en) 2013-09-23 2015-03-26 Rudolf Gmbh Polysiloxanes with quaternized heterocyclic groups
WO2015047786A1 (en) 2013-09-27 2015-04-02 The Procter & Gamble Company Hair conditioning compositions comprising low viscosity emulsified silicone polymers
US10160834B2 (en) 2016-07-13 2018-12-25 Momentive Performance Materials Inc. Low viscosity polyorganosiloxanes comprising quaternary ammonium groups, methods for the production and the use thereof
MX2020010427A (en) 2018-04-03 2020-10-28 Evonik Operations Gmbh Siloxanes for treating textiles and for use in cleaning and care formulations.

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0076625A1 (en) * 1981-10-03 1983-04-13 Dow Corning Limited Treating textile fibres
US4448810A (en) * 1982-10-15 1984-05-15 Dow Corning Limited Treating textile fibres with quaternary salt polydiorganosiloxane
EP0058493B1 (en) * 1981-02-05 1985-06-05 Toray Silicone Company Limited Fiber-treating compositions comprising two organo-functional polysiloxanes

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE666745A (en) * 1964-07-14 1966-01-12
US4323488A (en) * 1979-03-26 1982-04-06 Shin-Etsu Chemical Company Limited Method for the preparation of silicone-modified polyoxyalkylene polyethers and room temperature-curable compositions therewith
GB2107725B (en) * 1981-10-03 1985-02-27 Dow Corning Siloxane quaternary ammonium salt preparation
US4532132A (en) * 1983-04-11 1985-07-30 Dow Corning Corporation Skin care formulations comprising a water-in-mineral oil emulsion and siloxane compositions therefor
US4698406A (en) * 1986-11-04 1987-10-06 Dow Corning Corporation Curable organopolysiloxane composition
DE3705121A1 (en) * 1987-02-18 1988-09-01 Goldschmidt Ag Th POLYQUATERIAL POLYSILOXANE POLYMERS, THEIR PRODUCTION AND USE IN COSMETIC PREPARATIONS
DE3719086C1 (en) * 1987-06-06 1988-10-27 Goldschmidt Ag Th Diquartere polysiloxanes, their production and use in cosmetic preparations

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0058493B1 (en) * 1981-02-05 1985-06-05 Toray Silicone Company Limited Fiber-treating compositions comprising two organo-functional polysiloxanes
EP0076625A1 (en) * 1981-10-03 1983-04-13 Dow Corning Limited Treating textile fibres
US4448810A (en) * 1982-10-15 1984-05-15 Dow Corning Limited Treating textile fibres with quaternary salt polydiorganosiloxane

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0839947A2 (en) * 1996-11-04 1998-05-06 Schill &amp; Seilacher GmbH &amp; Co. Composition for the permanent hydrophilic treatment of polyolefines, use of the composition and the fibres treated therewith
EP0839947A3 (en) * 1996-11-04 1998-08-19 Schill &amp; Seilacher GmbH &amp; Co. Composition for the permanent hydrophilic treatment of polyolefines, use of the composition and the fibres treated therewith
US6008145A (en) * 1996-11-04 1999-12-28 Schill & Seilacher Gmbh & Co. Composition for the permanent hydrophilation of polyolefin fibres, use of the composition and fibres treated therewith
WO2002010502A1 (en) * 2000-07-27 2002-02-07 Wacker-Chemie Gmbh Method for saturating threads

Also Published As

Publication number Publication date
EP0339179A3 (en) 1991-09-18
DE3802622A1 (en) 1989-08-10
US4921895A (en) 1990-05-01
DE58902798D1 (en) 1993-01-07
EP0339179B1 (en) 1992-11-25
ES2037287T3 (en) 1993-06-16
DE3802622C2 (en) 1989-11-02

Similar Documents

Publication Publication Date Title
EP0339179B1 (en) Finishing composition for textile fibres or for textile products
DE60014811T2 (en) Fiber treatment agent containing siloxanes with amine and polyol functionality
EP0417047B1 (en) Microemulsions of aminopolysiloxans
DE69733519T2 (en) BLOCK COPOLYMERS BASED ON SILICONS AND AMINOPOLYALKYLENE OXIDES
DE69403431T2 (en) Process for softening textiles with reduced yellowing which uses a composition containing polyorganosiloxane
EP0313867B1 (en) Organopolysiloxanes with bunte salt groups
DE69102552T2 (en) Process for the treatment of fiber materials.
EP1560972B1 (en) Partially quaternised, amino-functional organopolysiloxanes and their use in aqueous systems
EP0057937B1 (en) Process for impregnating organic fibers
DE102006035511A1 (en) Novel polysiloxanes with quaternary ammonium groups, process for their preparation and their use as fabric softeners
DE102009029450A1 (en) Novel polysiloxanes with quaternary ammonium groups and their use
DE69003009T2 (en) Process for the treatment of fiber materials.
EP1258503A1 (en) Modified polyorganosiloxanes, aqueous emulsions, preparation and use thereof
DE102007015372A1 (en) Polysiloxane and textile auxiliaries containing a polysiloxane
DE10259291B4 (en) Highly concentrated, self-emulsifying preparations containing organopolysiloxanes and alkylammonium compounds and their use in aqueous systems
EP3303453B1 (en) Polyurethane-organopolysiloxanes
EP0016907B1 (en) Preparation for making wool shrink-proof
DE2844952C2 (en) Preparation for shrinking wool and process for making the preparation
DE3933971C2 (en) Liquid fabric softening composition and its use
EP0554863B1 (en) Process for impregnating organic fibers
DE10004321A1 (en) Organosilicon compounds with side chains containing quaternary ammonium groups derived from amine compounds with at least two tert. nitrogen atoms, used as softeners for textile treatment
EP0039783A2 (en) Process for the stabilisation of the dimensions of plane textile materials
DE102005056864B4 (en) Preparations based on ammonium- and polyether-modified organopolysiloxanes and their use for the finishing of textile substrates
DE60215370T2 (en) Compositions of polysiloxanes and quaternized fatty acid amides
DE10050933A1 (en) Flowable non-crosslinked polyorganosiloxane for treatment of fabrics contains at least one quaternary group comprising at least one nitrogen atom, and at least one further polar radical

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19890120

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): DE ES FR GB IT

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): DE ES FR GB IT

17Q First examination report despatched

Effective date: 19920514

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

ITF It: translation for a ep patent filed
AK Designated contracting states

Kind code of ref document: B1

Designated state(s): DE ES FR GB IT

GBT Gb: translation of ep patent filed (gb section 77(6)(a)/1977)
ET Fr: translation filed
REF Corresponds to:

Ref document number: 58902798

Country of ref document: DE

Date of ref document: 19930107

REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2037287

Country of ref document: ES

Kind code of ref document: T3

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
REG Reference to a national code

Ref country code: FR

Ref legal event code: CD

REG Reference to a national code

Ref country code: GB

Ref legal event code: IF02

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES;WARNING: LAPSES OF ITALIAN PATENTS WITH EFFECTIVE DATE BEFORE 2007 MAY HAVE OCCURRED AT ANY TIME BEFORE 2007. THE CORRECT EFFECTIVE DATE MAY BE DIFFERENT FROM THE ONE RECORDED.

Effective date: 20050114

REG Reference to a national code

Ref country code: FR

Ref legal event code: CD

Ref country code: FR

Ref legal event code: CJ

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: ES

Payment date: 20080130

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20080122

Year of fee payment: 20

Ref country code: GB

Payment date: 20080124

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 20080111

Year of fee payment: 20

REG Reference to a national code

Ref country code: GB

Ref legal event code: PE20

Expiry date: 20090113

REG Reference to a national code

Ref country code: ES

Ref legal event code: FD2A

Effective date: 20090115

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20090113

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: ES

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20090115