EP0339179A2 - Finishing composition for textile fibres or for textile products - Google Patents
Finishing composition for textile fibres or for textile products Download PDFInfo
- 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
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- 239000004753 textile Substances 0.000 title claims abstract description 23
- 239000000203 mixture Substances 0.000 title claims abstract description 15
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 33
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 22
- 239000000835 fiber Substances 0.000 claims abstract description 14
- -1 oxypropylene units Chemical group 0.000 claims abstract description 12
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 11
- 229920000570 polyether Polymers 0.000 claims abstract description 11
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 125000006353 oxyethylene group Chemical group 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 238000002360 preparation method Methods 0.000 claims description 18
- 125000000963 oxybis(methylene) group Chemical group [H]C([H])(*)OC([H])([H])* 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000000047 product Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 150000003961 organosilicon compounds Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000009988 textile finishing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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
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
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
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
R³ wie oben definiert ist,
R⁵ im Molekül gleich oder verschieden ist und einen Methyl- oder R⁶-Rest bedeutet,
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
R³ is as defined above,
R⁵ is the same or different in the molecule and represents a methyl or R⁶ radical,
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
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
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
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
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:
- 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--CH₃ ;
n = 200, m = 10
- 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--CH₃;
n = 200, m = 10
-
1. 20 % Siloxan A 1
5 % Siloxan B 3
30 % 1,2-Propylenglykol
45 % Wasser1. 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 % Wasser2. 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-Propylenglykol3. 60% siloxane A 4
6% siloxane B 2
34% 1,2-propylene glycol -
4. 5 % Siloxan A 2
5 % Siloxan B 5
90 % Wasser4. 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 % Wasser5. 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 % Wasser6. 2% siloxane A 3
2% siloxane B 6
96% water -
7. 10 % Siloxan A 4
5 % Siloxan B 7
85 % Wasser7. 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.
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.
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.
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-
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-
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,
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,
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-
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-
q = 25,
s> 1,
R¹² = - (CH₂) ₆-,
X ⊖ = H₃C-COO ⊖ mean.
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.
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.
Claims (6)
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.
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.
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.
R³ wie oben definiert ist,
R⁵ im Molekül gleich oder verschieden ist und einen Methyl- oder R⁶-Rest bedeutet,
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.
R³ is as defined above,
R⁵ is the same or different in the molecule and represents a methyl or R⁶ radical,
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.
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
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.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3802622A DE3802622A1 (en) | 1988-01-29 | 1988-01-29 | MEANS FOR CUTTING TEXTILE FIBER OR TEXTILE FIBER PRODUCTS |
| DE3802622 | 1988-01-29 |
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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0839947A2 (en) * | 1996-11-04 | 1998-05-06 | Schill & Seilacher GmbH & 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)
| 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 |
| US5354815A (en) * | 1992-06-05 | 1994-10-11 | Comfort Technologies | Polymers having enhanced hydrophilicity and thermal regulated properties and process of producing the same |
| TW282478B (en) * | 1992-06-05 | 1996-08-01 | Comfort Tech Inc | |
| 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 |
| US9399011B2 (en) | 2012-03-29 | 2016-07-26 | Momentive Performance Materials Gmbh | Low viscosity polyorganosiloxanes comprising quaternary ammonium groups, methods for the production and the use thereof |
| EP3357973B1 (en) | 2012-03-29 | 2019-07-31 | Momentive Performance Materials GmbH | Low viscosity polyorganosiloxanes comprising quaternary ammonium groups, methods for the production and the use thereof (ii) |
| 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 |
| MX363628B (en) | 2013-09-27 | 2019-03-28 | Procter & Gamble | 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 |
| WO2019192876A1 (en) | 2018-04-03 | 2019-10-10 | Evonik Degussa Gmbh | Siloxanes for treating textiles and for use in cleaning and care formulations |
Citations (3)
| 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)
| 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 |
-
1988
- 1988-01-29 DE DE3802622A patent/DE3802622A1/en active Granted
-
1989
- 1989-01-14 EP EP89100606A patent/EP0339179B1/en not_active Expired - Lifetime
- 1989-01-14 ES ES198989100606T patent/ES2037287T3/en not_active Expired - Lifetime
- 1989-01-14 DE DE8989100606T patent/DE58902798D1/en not_active Expired - Lifetime
- 1989-01-17 US US07/298,123 patent/US4921895A/en not_active Expired - Lifetime
Patent Citations (3)
| 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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0839947A2 (en) * | 1996-11-04 | 1998-05-06 | Schill & Seilacher GmbH & 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 & Seilacher GmbH & 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 |
|---|---|
| DE58902798D1 (en) | 1993-01-07 |
| ES2037287T3 (en) | 1993-06-16 |
| DE3802622A1 (en) | 1989-08-10 |
| EP0339179B1 (en) | 1992-11-25 |
| EP0339179A3 (en) | 1991-09-18 |
| US4921895A (en) | 1990-05-01 |
| DE3802622C2 (en) | 1989-11-02 |
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