DE10036533B4 - Use of polyquaternary polysiloxanes as washable hydrophilic plasticizers - Google Patents

Use of polyquaternary polysiloxanes as washable hydrophilic plasticizers Download PDF

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DE10036533B4
DE10036533B4 DE2000136533 DE10036533A DE10036533B4 DE 10036533 B4 DE10036533 B4 DE 10036533B4 DE 2000136533 DE2000136533 DE 2000136533 DE 10036533 A DE10036533 A DE 10036533A DE 10036533 B4 DE10036533 B4 DE 10036533B4
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radical
polysiloxanes
group
alkyl radicals
anionic
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DE10036533A1 (en
Inventor
Horst Dr. Lange
Roland Dr. Wagner
Anita Witossek
Karl-Heinz Stachulla
Siegfried Teuber
Albert Schnering
Annette MÖLLER
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Momentive Performance Materials GmbH
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GE Bayer Silicones GmbH and Co KG
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/373—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicones
    • C11D3/3742—Nitrogen containing silicones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/894—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/452—Block-or graft-polymers containing polysiloxane sequences containing nitrogen-containing sequences

Abstract

Verwendung von Polysiloxanen der allgemeinen Formel (III),

Figure 00000001
worin Z der Rest
Figure 00000002
ist, worin R6, R7, R8 C1-C22-Alkylreste sind und mindestens einer der Reste R6, R7, R8 mindestens 10 Kohlenstoffatome aufweist, R9, R10, R12, R14, R15 C1-C22-Alkylreste sind, R11 ein -O- oder -NR13- Rest ist, worin R13 C1-C4-Alkyl oder Wasserstoff ist, s = 2 bis 4, und
M ein zweiwertiger Rest, ausgewählt aus der Gruppe
Figure 00000003
ist, worin das N-Atom des Restes Z mit dem Rest M über das zur C-OH Gruppe im Rest M benachbarte Kohlenstoffatom verbunden ist, r eine Zahl von 0 bis 200 und B ein anorganisches oder organisches Anion ist, als Weichmacher in auf anionischen/nichtionischen Tensiden beruhenden Formulierungen zur Textilwäsche.Use of polysiloxanes of the general formula (III),
Figure 00000001
wherein Z is the radical
Figure 00000002
wherein R 6 , R 7 , R 8 are C 1 -C 22 -alkyl radicals and at least one of R 6 , R 7 , R 8 has at least 10 carbon atoms, R 9 , R 10 , R 12 , R 14 , R 15 are C 1 -C 22 -alkyl radicals, R 11 is an -O- or -NR 13 - radical, wherein R 13 is C 1 -C 4 -alkyl or hydrogen, s = 2 to 4, and
M is a divalent radical selected from the group
Figure 00000003
in which the N atom of the radical Z is connected to the radical M via the carbon atom adjacent to the C-OH group in the radical M, r is a number from 0 to 200 and B is an inorganic or organic anion, as a plasticizer in on anionic / nonionic surfactant based textile laundering formulations.

Description

Die Erfindung betrifft die Verwendung von polyquarternären Polysiloxanen.The This invention relates to the use of polyquaternary polysiloxanes.

Polysiloxane die Aminogruppen enthalten und als textile Weichmacher verwendet werden sind bereits aus der EP 441 530 A2 bekannt. Die US 5 591 880 A und US 5 650 529 A offenbaren die Einführung von durch Ethylenoxid-/Propylenoxideinheiten modifizierten Aminostrukturen als Seitenketten, die eine Verbesserung des Effekts als textiler Weichmacher hervorrufen. Die Alkylenoxideinheiten erlauben hierbei die gezielte Einstellung der hydrophilen-hydrophoben Balance. Nachteilig bei der Herstellung der Verbindungen in der Synthese ist die schwierige eingeschlossene Veresterung von Aminoalkoholen mit siloxangebundenen Carbonsäuregruppen. Zusätzliche Schwierigkeiten ergeben sich bezüglich der weichmachenden Eigenschaften durch die generelle Kammstruktur der Produkte. Die US 5 807 956 A und die US 5 981 681 A beschreiben zur Beseitigung dieser Nachteile, daß α,ω-epoxydmodifizierte Siloxane mit α,ω-aminofunktionalisierten Alkylenoxiden umgesetzt werden sollen, und diese Produkte als hydrophile Weichmacher einzusetzen. Polysiloxanes which contain amino groups and are used as textile softening agents are already known from US Pat EP 441 530 A2 known. The US 5 591 880 A and US 5 650 529 A disclose the introduction of ethylene oxide / propylene oxide moieties modified amino structures as side chains, which produce an improvement in the effect as a textile plasticizer. The alkylene oxide units allow the targeted adjustment of the hydrophilic-hydrophobic balance. Disadvantageous in the preparation of the compounds in the synthesis is the difficult entrapped esterification of amino alcohols with siloxane-bound carboxylic acid groups. Additional difficulties arise in terms of plasticizing properties due to the general comb structure of the products. The US 5 807 956 A and the US 5,981,681 A describe to eliminate these disadvantages that α, ω-epoxy-modified siloxanes are reacted with α, ω-amino-functionalized alkylene oxides, and to use these products as hydrophilic plasticizers.

Zur Verbesserung der Substantivität sind Versuche unternommen worden, quarternäre Ammoniumgruppen in alkylenoxidmodifizierte Siloxane einzuführen. Verzweigte alkylenoxidmodifizierte quarternäre Polysiloxane können durch Kondensation von α,ω-OH-terminierten Polysiloxanen und Trialkoxysilanen synthetisiert werden. Die quarternäre Ammoniumstruktur wird über das Silan eingebracht, wobei das quarternäre Stickstoffatom durch Alkylenoxideinheiten substituiert ist, wie in der US 5 625 024 A offenbart. Streng kammartige alkylenoxidmodifizierte quarternäre Polysiloxane sind bereits in der US 5 098 979 A beschrieben. Die Hydroxylgruppen von kammartig substituierten Polyethersiloxanen werden mit Epichlorhydrin in die entsprechenden Chlorhydrinderivate überführt. Daran schließt sich eine Quaternierung mit tertiären Aminen an. Nachteilig an dieser Synthese ist die Verwendung von Epichlorhydrin und die relativ geringe Reaktivität der Chlorhydrin-Gruppierung während der Quaternierung.To improve substantivity, attempts have been made to introduce quaternary ammonium groups into alkylene oxide-modified siloxanes. Branched alkylene oxide-modified quaternary polysiloxanes can be synthesized by condensation of α, ω-OH-terminated polysiloxanes and trialkoxysilanes. The quaternary ammonium structure is introduced via the silane, the quaternary nitrogen atom being substituted by alkylene oxide units, as in US Pat US Pat. No. 5,625,024 disclosed. Strictly comb-like alkylene oxide-modified quaternary polysiloxanes are already in the US 5 098 979 A described. The hydroxyl groups of comb-like substituted polyethersiloxanes are converted with epichlorohydrin into the corresponding chlorohydrin derivatives. This is followed by quaternization with tertiary amines. A disadvantage of this synthesis is the use of epichlorohydrin and the relatively low reactivity of the chlorohydrin moiety during quaternization.

Aus diesem Grund werden die Hydroxylgruppen kammartig substituierter Polyethersiloxane alternativ mit Chloressigsäure verestert. Durch die Carbonylaktivierung kann die abschließende Quaternierung erleichtert vollzogen werden, wie in der US 5 153 294 A der US 5 166 297 A offenbart. For this reason, the hydroxyl groups of comb-substituted polyether siloxanes are alternatively esterified with chloroacetic acid. By Carbonylaktivierung the final quaternization can be accomplished, as in the US 5 153 294 A of the US 5,166,297 A. disclosed.

Einen grundsätzlich anderen Ansatz offenbart die DE 32 36 466 A1 . Die Umsetzung von OH-terminierten Siloxanen mit quarternäre Ammoniumstrukturen enthaltenden Alkoxysilanen liefert reaktive Zwischenprodukte, die mit geeigneten Vernetzungsagenzien, wie Trialkoxysilanen, auf der Faseroberfläche zu waschbeständigen Schichten vernetzen sollen. Ein wesentlicher Nachteil dieses Ansatzes ist es, daß die über Stunden notwendige Stabilität eines wässrigen Ausrüstungsbades nicht garantiert werden kann und unvorhergesehene Vernetzungsreaktionen im Bad bereits vor der Textilausrüstung auftreten können.A fundamentally different approach reveals the DE 32 36 466 A1 , The reaction of OH-terminated siloxanes with quaternary ammonium-containing alkoxysilanes provides reactive intermediates which are to crosslink with suitable crosslinking agents such as trialkoxysilanes on the fiber surface to wash-resistant layers. A major disadvantage of this approach is that the stability required for hours of an aqueous finishing bath can not be guaranteed and unforeseen crosslinking reactions in the bathroom can occur even before the textile finish.

Die EP 0 282 720 A2 beschreibt polyquarternäre Polysilxan-Polymere, deren Herstellung durch Reaktion von α,ω-Diepoxiden mit tertiären Aminen in Gegenwart von Säuren und Verwendung in kosmetischen Zubereitungen als Haarbehandlungsmittel.The EP 0 282 720 A2 describes polyquaternary polysiloxane polymers, their preparation by reaction of α, ω-diepoxides with tertiary amines in the presence of acids and use in cosmetic preparations as hair treatment agents.

Die WO 96/26260 A1 offenbart die Anwendung der diquaternären Polysiloxane in Reinigungszusammensetzungen für harte Oberflächen. In diesen Formulierungen dürfen maximal 1 % der gesamten Tenside anionische Tenside sein, da die Anwesenheit anionischer Tenside zur Bildung von Komplexen mit den kationischen Polysiloxan-Verbindungen führen soll, die so ihrer Wirksamkeit beraubt werden. Es bestand daher ein Vorurteil, die erfindungsgemäß verwendeten Polysiloxan-Verbindungen in Anwendungen zu verwenden, die den Einsatz größerer Mengen anionischer Tenside erfordern.The WO 96/26260 A1 discloses the use of the diquaternary polysiloxanes in cleaning compositions for hard surfaces. In these formulations may a maximum of 1% of the total surfactants anionic surfactants, as the Presence of anionic surfactants to form complexes with the cationic polysiloxane compounds, so its effectiveness be robbed. There was therefore a prejudice that used according to the invention Polysiloxane compounds to be used in applications involving the use of larger amounts of anionic surfactants require.

Die DE 19944416 A1 offenbart ein Klarspülmittel, dass die erfindungsgemäß verwendeten Siloxane enthält. Das Klarspülmittel dient dem Einsatz in Geschirrspülmitteln und führt insbesondere zu einer Verkürzung der Trocknungszeit der zu behandelnden Substraten mit ihrer harten Oberfläche. Es findet sich kein Hinweis auf Waschmittelformulierungen für die Textilwäsche. Die Oberflächen von Textilfasern und Geschirrspülsubstraten, wie keramische Substrate, sind naturgemäß in ihren Eigenschaften nicht vergleichbar. Der Fachmann konnte somit der DE 19944416 A1 keinen Hinweis auf die Verwendung der kationischen Siloxan-Verbindungen in Waschmittelformulierungen entnehmen. Dies gilt in analoger Weise für die DE 19853720 A1 , die Allzweckreiniger für harte Oberflächen offenbart, die die erfindungsgemäß verwendeten Siloxane enthalten.The DE 19944416 A1 discloses a rinse aid containing the siloxanes used in the invention. The rinse aid serves for use in dishwashing detergents and in particular leads to a shortening of the drying time of the substrates to be treated with their hard surface. There is no reference to laundry detergent formulations for textile laundry. The surfaces of textile fibers and dishwashing substrates, such as ceramic substrates, are by nature not comparable in their properties. The expert could thus the DE 19944416 A1 do not refer to the use of the cationic siloxane compounds in detergent formulations. This applies analogously to the DE 19853720 A1 , which discloses general purpose hard surface cleaners containing the siloxanes used in the invention.

Weiterhin sind aus der WO 99/32539 A1 strukturell verschiedene kationische Polysiloxane bekannt. Die Autoren der WO 99/32539 A1 verleihen ihrer Erwartung Ausdruck, dass diese Polysiloxane in üblichen Anwendungen kationischer Polymere und Siloxanpolymere Verwendung finden können. Unter diesen Anwendungen finden sich erwartungsgemäß auch solche Anwendungen, wie kosmetische Anwendungen und Faserbehandlungsanwendungen. Es gibt allerdings keinen Hinweis auf die Verwendung der dort offenbarten kationischen Polysiloxane in anionische Tenside enthaltenden Waschmittelformulierungen für die Textilwäsche. Der Fachmann konnte somit der WO 99/32539 A1 keinen Hinweis auf die Verwendung der erfindungsgemäß verwendeten Siloxane in anionische Tenside enthaltenden Waschmittelformulierungen finden.Furthermore, structurally different cationic polysiloxanes are known from WO 99/32539 A1. The authors of WO 99/32539 A1 express their expectation that these polysiloxanes can be used in conventional applications of cationic polymers and siloxane polymers. As expected, these applications also include such applications as cosmetic applications and fiber treatment applications. However, there is no indication of the use of the cationic polysiloxanes disclosed therein in laundry detergent formulations containing textile surfactants containing anionic surfactants. The person skilled in the art could thus find no indication of the use of the siloxanes according to the invention in detergent formulations containing anionic surfactants in WO 99/32539 A1.

Aus dem Stand der Technik sind keine befriedigenden Lösungen für das Problem gefunden worden, den für fortschrittliche Silicone typischen weichen Griff und die ausgeprägte Hydrophilie nach Erstausrüstung eines Textilmaterials auch dann zu gewärhrleisten, wenn dieses dem Angriff aggressiver Detergenzienformulierungen im Verlauf wiederholter Waschprozesse bei gegebenenfalls. erhöhter Temperatur ausgesetzt wird.Out The prior art is not a satisfactory solution to the problem been found for advanced silicone typical soft feel and pronounced hydrophilicity after original equipment one To ensure that textile material is if this is the attack of aggressive detergent formulations in Course of repeated washing processes if necessary. elevated temperature is suspended.

In der EP 0 282 720 A2 wird ein Verfahren zur Herstellung von Verbindungen, beschrieben, in der die Reaktion von α,ω-Diepoxiden mit di-tertiärem Aminen in Gegenwart von Säuren zu polymeren Strukturen erfolgt. Eine Herstellung über quarternäre Z1 und Z2-Gruppen ist nichts offenbart worden.In the EP 0 282 720 A2 describes a process for preparing compounds, in which the reaction of α, ω-diepoxides with di-tertiary amine in the presence of acids to polymeric structures. A preparation on quaternary Z 1 and Z 2 groups has not been disclosed.

Aufgabe der vorliegenden Erfindung ist es deshalb gewesen Weichmacher zu finden, die einen silicontypischen weichen Griff und eine ausgeprägte Hydrophilie verleihen, wobei dieses Eigenschaftsbild auch nach Einwirkung von Detergenzienformulierungen, nach wiederholten Waschprozessen bei gegebenenfalls erhöhter Temperatur nicht verloren geht.task Therefore, it has been the plasticizer of the present invention find a silicate-typical soft feel and a pronounced hydrophilicity lend this property image even after exposure to Detergent formulations, after repeated washing processes possibly elevated Temperature is not lost.

Gegenstand der vorliegenden Erfindung ist daher die Verwendung von Polysiloxanen der allgemeinen Formel (III),

Figure 00030001
worin Z der Rest
Figure 00040001
ist, worin R6, R7, R8 C1-C22-Alkylreste sind und mindestens einer der Reste R6, R7, R8 mindestens 10 Kohlenstoffatome aufweist, R9, R10, R12, R14, R15 C1-C22-Alkylreste sind, R11 ein -O- oder -NR13- Rest ist, worin R13 C1-C4-Alkyl oder Wasserstoff ist, s = 2 bis 4, und
M ein zweiwertiger Rest, ausgewählt aus der Gruppe
Figure 00040002
ist, worin das N-Atom des Restes Z mit dem Rest M über das zur C-OH Gruppe im Rest M benachbarte Kohlenstoffatom verbunden ist, r eine Zahl von 0 bis 200 und B ein anorganisches oder organisches Anion ist, als Weichmacher in auf anionischen/nichtionischen Tensiden beruhenden Formulierungen zur Textilwäsche, insbesondere die Verwendung in Waschmitteln für Textilien sowie die Bereitstellung von Waschmittelformulierungen für Textilien, enthaltend anionische und nichtionische Tenside sowie mindestens ein Polysiloxan der allgemeinen Formel (III).The present invention therefore provides the use of polysiloxanes of the general formula (III)
Figure 00030001
wherein Z is the radical
Figure 00040001
wherein R 6 , R 7 , R 8 are C 1 -C 22 -alkyl radicals and at least one of R 6 , R 7 , R 8 has at least 10 carbon atoms, R 9 , R 10 , R 12 , R 14 , R 15 are C 1 -C 22 -alkyl radicals, R 11 is an -O- or -NR 13 - radical, wherein R 13 is C 1 -C 4 -alkyl or hydrogen, s = 2 to 4, and
M is a divalent radical selected from the group
Figure 00040002
in which the N atom of the radical Z is connected to the radical M via the carbon atom adjacent to the C-OH group in the radical M, r is a number from 0 to 200 and B is an inorganic or organic anion, as a plasticizer in on anionic / nonionic surfactant-based formulations for textile washing, in particular the use in laundry detergents for textiles and the provision of laundry detergent formulations for textiles containing anionic and nonionic surfactants and at least one polysiloxane of the general formula (III).

Die Reste R6, R7, R8, sowie die Reste R9, R10, R12, R14 und R15 können im Molekül gleich oder verschieden sein. Bevorzugt sind solche Verbindungen, bei denen zwei der Reste R6, R7, R8 niedere Alkylreste mit 1 bis 4 Kohlenstoffatomen sind und der verbleibende dritte Rest ein langkettiger Kohlenwasserstoffrest mit mindestens 10 Kohlenstoffatomen ist. Unter den langkettigen Kohlenwasserstoffresten sind insbesondere gesättigten und ungesättigten verzweigte oder unverzweigte Kohlenwasserstoffreste bevorzugt, die sich von den natürlich vorkommenden Fettsäuren ableiten.The radicals R 6 , R 7 , R 8 , and the radicals R 9 , R 10 , R 12 , R 14 and R 15 may be the same or different in the molecule. Preference is given to those compounds in which two of the radicals R 6 , R 7 , R 8 are lower alkyl radicals having 1 to 4 carbon atoms and the remaining third radical is a long-chain hydrocarbon radical having at least 10 carbon atoms. Among the long-chain hydrocarbon radicals, preference is given in particular to saturated and unsaturated branched or unbranched hydrocarbon radicals which are derived from the naturally occurring fatty acids.

Liegen die Reste R9, R10 und R12 nebeneinander vor, sind diejenigen Verbindungen bevorzugt, bei denen R9 und R10 einen niederen Kohlenwasserstofrest mit 1 bis 4 Kohlenstoffatomen bedeutet und der Rest R12 von einer Fettsäure R12COOH abgeleitet ist, die mindestens 8 Kohlenstoffatome aufweist.If the radicals R 9 , R 10 and R 12 are present next to one another, those compounds are preferred in which R 9 and R 10 are a lower hydrocarbon radical having 1 to 4 carbon atoms and the radical R 12 is derived from a fatty acid R 12 COOH, which has at least 8 carbon atoms.

In EP 0 282 720 A2 und DE 37 19 086 C1 wird die Verwendung der jeweils offenbarten Verbindungen in kosmetischen Formulierungen, speziell in der Haarpflege beschrieben. Als Vorteile werden generell eine verbesserte Kämmbarkeit, ein guter Glanz, eine hohe antistatische Effektivität und bevorzugt in EP 0 282 720 A2 eine verbesserte Auswaschbeständigkeit genannt.In EP 0 282 720 A2 and DE 37 19 086 C1 describes the use of the respectively disclosed compounds in cosmetic formulations, especially in hair care. As advantages are generally improved combability, a good gloss, high antistatic effectiveness and preferably in EP 0 282 720 A2 called an improved washout resistance.

Die letztgenannte Eigenschaft ist nicht mit einer Waschbeständigkeit in erfindungsgemäßen Sinne gleichzusetzen. Während sich die Auswaschbeständigkeit aus Haaren auf den kurzzeitigen Angriff von vornehmlich Wasser und sehr milden, die Haut nicht irritierenden Tensiden bezieht, haben waschbeständige, hydrophile Weichmacher für Textilien dem Angriff konzentrierter Tensidlösungen mit hohem Fett- und Schmutzlösevermögen zu widerstehen. Diesen Tensidsystemen werden in modernen Waschmitteln stark alkalische Komplexbildner, oxydativ wirkende Bleichmittel und komplexe Enzymsysteme hinzugefügt. Die Einwirkung erfolgt häufig über Stunden bei erhöhten Temperaturen. Aus diesen Gründen heraus ist eine Übertragung von Erfahrungen aus dem Kosmetikbereich auf das Gebiet der waschbeständigen Textilweichmacher nicht möglich. Die DE 32 36 466 A1 offenbart, daß zur Erzielung einer waschbeständigen Textilausrüstung auf vernetzungsfähige Systeme zurück zu greifen gewesen wäre.The latter property is not to be equated with a washing resistance in the sense of the invention. While hair washout refers to the brief attack of primarily water and very mild non-irritating surfactants, wash resistant, hydrophilic fabric softeners are designed to withstand the attack of concentrated surfactant solutions having high fat and soil release properties. To these surfactant systems, highly alkaline complexing agents, oxidative bleaching agents and complex enzyme systems are added in modern detergents. The action is often over hours at elevated temperatures. For these reasons, a transfer of experience in the field of cosmetics in the field of wash-resistant fabric softeners is not possible. The DE 32 36 466 A1 discloses that in order to achieve a wash resistant textile finish, crosslinkable systems would have to be resorted to.

Es war weiterhin nicht ableitbar, daß die Verbindungen gemäß EP 0 282 720 A2 und DE 37 19 086 C1 in vorteilhafter Weise als interne Weichmacher in auf anionischen/nichtionogenen Tensiden beruhenden Formulierungen zur Wäsche von Textilien und Fasern benutzt werden können. Für diesen Fall gelten ebenfalls die zu den aggressiven Waschmittelsystemen, den erhöhten Temperaturen und langen Einwirkzeiten gemachten Überlegungen.It was also not deducible that the compounds according to EP 0 282 720 A2 and DE 37 19 086 C1 can be advantageously used as internal plasticizers in formulations based on anionic / nonionic surfactants for washing textiles and fibers. For this case, the considerations made on the aggressive detergent systems, the elevated temperatures and long exposure times also apply.

Claims (2)

Verwendung von Polysiloxanen der allgemeinen Formel (III),
Figure 00070001
worin Z der Rest
Figure 00070002
ist, worin R6, R7, R8 C1-C22-Alkylreste sind und mindestens einer der Reste R6, R7, R8 mindestens 10 Kohlenstoffatome aufweist, R9, R10, R12, R14, R15 C1-C22-Alkylreste sind, R11 ein -O- oder -NR13- Rest ist, worin R13 C1-C4-Alkyl oder Wasserstoff ist, s = 2 bis 4, und M ein zweiwertiger Rest, ausgewählt aus der Gruppe
Figure 00070003
ist, worin das N-Atom des Restes Z mit dem Rest M über das zur C-OH Gruppe im Rest M benachbarte Kohlenstoffatom verbunden ist, r eine Zahl von 0 bis 200 und B ein anorganisches oder organisches Anion ist, als Weichmacher in auf anionischen/nichtionischen Tensiden beruhenden Formulierungen zur Textilwäsche.Use of polysiloxanes of the general formula (III),
Figure 00070001
wherein Z is the radical
Figure 00070002
wherein R 6 , R 7 , R 8 are C 1 -C 22 -alkyl radicals and at least one of R 6 , R 7 , R 8 has at least 10 carbon atoms, R 9 , R 10 , R 12 , R 14 , R 15 are C 1 -C 22 -alkyl radicals, R 11 is an -O- or -NR 13 radical in which R 13 is C 1 -C 4 -alkyl or hydrogen, s = 2 to 4, and M is a bivalent radical, selected from the group
Figure 00070003
in which the N atom of the radical Z is connected to the radical M via the carbon atom adjacent to the C-OH group in the radical M, r is a number from 0 to 200 and B is an inorganic or organic anion, as a plasticizer in on anionic / nonionic surfactant based textile laundering formulations. Waschmittelformulierung für Textilien, enthaltend anionische und nichtionische Tenside sowie mindestens ein Polysiloxan der allgemeinen Formel (III), wie im Anspruch 1 definiert.Detergent formulation for textiles containing anionic and nonionic surfactants and at least one polysiloxane of the general Formula (III) as defined in claim 1.
DE2000136533 2000-07-27 2000-07-27 Use of polyquaternary polysiloxanes as washable hydrophilic plasticizers Expired - Fee Related DE10036533B4 (en)

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Application Number Priority Date Filing Date Title
DE2000136533 DE10036533B4 (en) 2000-07-27 2000-07-27 Use of polyquaternary polysiloxanes as washable hydrophilic plasticizers
DE10066215A DE10066215B4 (en) 2000-07-27 2000-07-27 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

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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Families Citing this family (94)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10221521A1 (en) 2002-05-14 2003-12-04 Ge Bayer Silicones Gmbh & Co Formulations of silicone softeners for textile finishing
AU2003302035A1 (en) 2002-11-04 2004-06-15 Ge Bayer Silicones Gmbh And Co. Kg Formulations used for the treatment of substrate surfaces
DE10316662A1 (en) 2003-04-11 2004-11-11 Ge Bayer Silicones Gmbh & Co. Kg Reactive amino and / or ammonium polysiloxane compounds
DE102004006300A1 (en) * 2004-02-09 2005-09-08 Schill + Seilacher "Struktol" Ag Branched polyorganosiloxanes with quaternary ammonium groups
DE102004025131A1 (en) * 2004-05-14 2005-12-08 Schill + Seilacher "Struktol" Ag Derivatized, permanently quaternized nitrogen atoms, straight-chain or branched amino-functional organopolysiloxanes
US8013097B2 (en) 2007-04-11 2011-09-06 Dow Corning Corporation Silicone polyether block copolymers having organofunctional endblocking groups
WO2011042409A2 (en) 2009-10-05 2011-04-14 Momentive Performance Materials Gmbh Aqueous emulsions of polyorganosiloxanes
US8933131B2 (en) 2010-01-12 2015-01-13 The Procter & Gamble Company Intermediates and surfactants useful in household cleaning and personal care compositions, and methods of making the same
WO2012003300A2 (en) 2010-07-02 2012-01-05 The Procter & Gamble Company Filaments comprising a non-perfume active agent nonwoven webs and methods for making same
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US20120172281A1 (en) 2010-07-15 2012-07-05 Jeffrey John Scheibel Detergent compositions comprising microbially produced fatty alcohols and derivatives thereof
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US20140371435A9 (en) 2011-06-03 2014-12-18 Eduardo Torres Laundry Care Compositions Containing Thiophene Azo Dyes
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Citations (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2912485A1 (en) * 1979-03-29 1980-10-09 Henkel Kgaa NEW QUARTAERE POLYSILOXAN DERIVATIVES, THEIR USE IN HAIR COSMETICS, AND THEIR WASHING AND TREATMENT PRODUCTS CONTAINING THEM
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
US5026489A (en) * 1990-04-04 1991-06-25 Dow Corning Corporation Softening compositions including alkanolamino functional siloxanes
US5110891A (en) * 1991-04-11 1992-05-05 Dow Corning Corporation Amine functional siloxanes
US5248783A (en) * 1991-11-06 1993-09-28 Siltech Inc. Silicone alkoxylated esters carboxylate salts
US5300167A (en) * 1992-01-03 1994-04-05 Kimberly-Clark Method of preparing a nonwoven web having delayed antimicrobial activity
US5306434A (en) * 1992-10-20 1994-04-26 Alberto-Culver Company Hair care composition containing dispersed silicone oil
US5370971A (en) * 1991-11-01 1994-12-06 Kansai Paint Co., Ltd. Epoxy based photopolymerizable composition
WO1996026260A1 (en) * 1995-02-23 1996-08-29 Unilever Plc Cleaning composition comprising quaternised poly-dimethylsiloxane and nonionic surfactant
US5569732A (en) * 1993-06-11 1996-10-29 Kimberly-Clark Corporation Antimicrobial siloxane quaternary ammonium salts
WO1999032539A1 (en) * 1997-12-19 1999-07-01 The Procter & Gamble Company Multi-cationic silicone polymers
DE19852621A1 (en) * 1998-11-14 2000-05-18 Hansa Textilchemie Gmbh Permanent means of finishing fibers or fiber products
DE19853720A1 (en) * 1998-11-20 2000-05-25 Henkel Kgaa Aqueous cleaners for hard surfaces, e.g. floors in public areas, contain surfactant, including anionic surfactant, and diquaternary polysiloxane to reduce drying time
DE19944416A1 (en) * 1999-09-16 2001-03-22 Henkel Kgaa Rinse aid

Patent Citations (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2912485A1 (en) * 1979-03-29 1980-10-09 Henkel Kgaa NEW QUARTAERE POLYSILOXAN DERIVATIVES, THEIR USE IN HAIR COSMETICS, AND THEIR WASHING AND TREATMENT PRODUCTS CONTAINING THEM
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
US5026489A (en) * 1990-04-04 1991-06-25 Dow Corning Corporation Softening compositions including alkanolamino functional siloxanes
US5110891A (en) * 1991-04-11 1992-05-05 Dow Corning Corporation Amine functional siloxanes
US5370971A (en) * 1991-11-01 1994-12-06 Kansai Paint Co., Ltd. Epoxy based photopolymerizable composition
US5248783A (en) * 1991-11-06 1993-09-28 Siltech Inc. Silicone alkoxylated esters carboxylate salts
US5300167A (en) * 1992-01-03 1994-04-05 Kimberly-Clark Method of preparing a nonwoven web having delayed antimicrobial activity
US5306434A (en) * 1992-10-20 1994-04-26 Alberto-Culver Company Hair care composition containing dispersed silicone oil
US5569732A (en) * 1993-06-11 1996-10-29 Kimberly-Clark Corporation Antimicrobial siloxane quaternary ammonium salts
WO1996026260A1 (en) * 1995-02-23 1996-08-29 Unilever Plc Cleaning composition comprising quaternised poly-dimethylsiloxane and nonionic surfactant
WO1999032539A1 (en) * 1997-12-19 1999-07-01 The Procter & Gamble Company Multi-cationic silicone polymers
DE19852621A1 (en) * 1998-11-14 2000-05-18 Hansa Textilchemie Gmbh Permanent means of finishing fibers or fiber products
DE19853720A1 (en) * 1998-11-20 2000-05-25 Henkel Kgaa Aqueous cleaners for hard surfaces, e.g. floors in public areas, contain surfactant, including anionic surfactant, and diquaternary polysiloxane to reduce drying time
DE19944416A1 (en) * 1999-09-16 2001-03-22 Henkel Kgaa Rinse aid

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
JP 08257391 A (abstract), In: Pat. Abstr. of Jp. [CD-ROM] *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10494767B2 (en) 2013-12-09 2019-12-03 The Procter & Gamble Company Fibrous structures including an active agent and having a graphic printed thereon
US11624156B2 (en) 2013-12-09 2023-04-11 The Procter & Gamble Company Fibrous structures including an active agent and having a graphic printed thereon
US11795622B2 (en) 2013-12-09 2023-10-24 The Procter & Gamble Company Fibrous structures including an active agent and having a graphic printed thereon

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