EP1199350B1 - Verwendung von quaternären Polysiloxanen in Waschmittelformulierungen - Google Patents
Verwendung von quaternären Polysiloxanen in Waschmittelformulierungen Download PDFInfo
- Publication number
- EP1199350B1 EP1199350B1 EP01123706A EP01123706A EP1199350B1 EP 1199350 B1 EP1199350 B1 EP 1199350B1 EP 01123706 A EP01123706 A EP 01123706A EP 01123706 A EP01123706 A EP 01123706A EP 1199350 B1 EP1199350 B1 EP 1199350B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- radical
- carbon atoms
- alkyl
- radicals
- general formula
- 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.)
- Expired - Lifetime
Links
- XQBHJXLMVUHQAF-UHFFFAOYSA-N CC(CC(CC1)C=C)C1(C)O Chemical compound CC(CC(CC1)C=C)C1(C)O XQBHJXLMVUHQAF-UHFFFAOYSA-N 0.000 description 2
- DISSYNSLBWSJHH-UHFFFAOYSA-N CC(C1)CC=C(C)C1O Chemical compound CC(C1)CC=C(C)C1O DISSYNSLBWSJHH-UHFFFAOYSA-N 0.000 description 1
- CKPQAKDCQGMTSO-UHFFFAOYSA-N CC(CC1)CC(C)C1O Chemical compound CC(CC1)CC(C)C1O CKPQAKDCQGMTSO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
Definitions
- the invention relates to the use of quaternary Polysiloxanes in detergent formulations.
- Drum washing machines like those in European households are common, usually wash in two steps.
- the Main wash is the laundry first with the help of a Detergent (powder or liquid) cleaned. Subsequently there are several rinses with clear water. The last one these rinses can be used as fabric softener for after-treatment be added. This should give the laundry a soft, Give a fluffy feel.
- the consumer should now have a product that is easier to handle be given to hand, which repeated dosing processes replaced by a single dose.
- EP-A-0 151 938 describes so-called “two in One "detergent formulations, wherein anionic surfactants and quaternary alkylammonium surfactants with the aid of carrier materials be combined.
- Polydimethylsiloxanes can also be used as plasticizers Component used in "Two in One" detergent formulations become. If you want to combine the washing and fabric softening process, however, such formulations have the disadvantage that Polydimethylsiloxanes due to their high hydrophobicity and oleophobicity on deposits and "build-up" effects in washing machines and run on the laundry.
- Quaternary polysiloxanes are also known and for example in EP-A-0 282 720 and in DE-A-37 19 086. Such connections are so far especially for their conditioning properties known in hair cosmetics.
- the object of the present invention was Provide detergent formulations that the laundry and Combine the softener process and a clear after washing leave a measurable softening effect in the textiles.
- radical M a divalent hydrocarbon radical with at least 4 carbon atoms, which has a hydroxyl group and which can be interrupted by at least one oxygen atom, the N atom of the radical Z with the radical M via that to the C-OH group in the radical M adjacent carbon atom are connected
- the two Z radicals have the same or different meaning.
- radicals R 1 , R 2 , R 3 the alkyl radicals with 1 to 22 carbon atoms or alkenyl radicals with 2 to 22 carbon atoms, where the alkyl or alkenyl radicals can have hydroxyl groups and at least one of the radicals R 1 , R 2 , R 3 has at least 10 carbon atoms are alkyl radicals, such as the methyl, ethyl, octyl, dodecyl, hexadecyl or octadecyl radical; Hydroxyalkyl radicals, such as the hydroxyethyl radical; Alkenyl residues, such as the allyl or vinyl residue.
- radicals R 4 , R 5 , R 7 , R 9 , R 10 the alkyl radicals having 1 to 22 carbon atoms or alkenyl radicals having 2 to 22 carbon atoms, where the alkyl or alkenyl radicals can have hydroxyl groups, are alkyl radicals, such as methyl -, ethyl, octyl, dodecyl, hexadecyl or octadecyl; Hydroxyalkyl radicals, such as the hydroxyethyl radical; Alkenyl residues, such as the allyl or vinyl residue.
- R 8 the alkyl or hydroxyalkyl radical having 1 to 4 carbon atoms or hydrogen radical, are the hydrogen radical; Alkyl radicals such as the methyl, ethyl, isopropyl or butyl radical and hydroxyalkyl radicals such as the hydroxyethyl radical.
- a - an inorganic or organic anion, which derives from a common physiologically compatible acid HA, are Cl - , Br - , SO 4 2- , HSO 4 - , H 3 CSO 4 - , H 3 CCO 2 - , citrate and tosylate.
- radical Z 1 examples are H-, HO-, H 3 C-CH 2 O-, (H 3 C) 2 CHO-, H 3 C (CH 2 ) 7 -,
- Examples of Y a divalent hydrocarbon radical with at least 2 carbon atoms, which have a hydroxyl group and which can be interrupted by at least one oxygen or nitrogen atom, are - (CH 2 ) 2 -, - (CH 2 ) 3 -, - (CH 2 ) 6 -, - (CH 2 ) 12 -, - (CH 2 ) 2 -O- (CH 2 ) 2 -, -CH 2 -O-CH 2 -,
- R 11 , R 12 , R 13 , R 14 which are the same or different and are alkyl radicals having 1 to 4 carbon atoms or benzyl radicals, or R 11 and R 13 or R 12 and R 14 can each be constituents of a bridging alkylene radical are alkyl radicals such as methyl, ethyl, isopropyl or butyl radicals and benzyl radicals such as the benzyl radical. If R 11 and R 13 or R 12 and R 14 are constituents of a bridging alkylene radical, this part of the molecule can have the following structure:
- R 11 , R 12 , R 13 , R 14 radicals are the methyl and ethyl radicals.
- R 15 an alkyl radical having 1 to 20 carbon atoms
- alkyl radicals such as the methyl, ethyl, octyl, dodecyl, hexadecyl or octadecyl radical.
- Detergents are the formulations that are commercially available in this field in the form of powders, granules, pearls, tablets, Pastes, gels or liquids. They are mostly considered Heavy duty detergent formulated with a universal range of uses essentially contain solid or liquid carriers and various functional ingredients such as surfactants, inorganic polymeric builders, enzymes, bleaching systems, optical brighteners, soil release polymers, foam inhibitors, Fillers, process aids, stabilizers.
- Anionic compounds such as alkylbenzenesulfonates (LAS) are predominantly used as surfactants, optionally in combination with fatty alcohol polyglycol ethers, fatty alcohol sulfates, ⁇ -olefin sulfonates, ester sulfates and more recently also alkylpolyglycosides (APG) and fatty acid glucamides (GA); Zeolites, polycarboxylates, polyvinylpyrrolidones and amorphous anhydrous sodium silicates and layered silicates are also used as builders, with citric acid often being used as a co-builder; Components of the bleaching systems are in particular perborates and sodium percarbonate with the use of N-acetyl compounds, N, N, N ', N'-tetraacetylethylene diamine or p-nonyloxybenzenesulfonate as activators; Stilbenes and distyrylbiphenyls are used as optical
- test formulations used are as follows together:
- Liquid detergent base (component A):
- Anionic surfactants Na-alkylbenzenesulfonate 21.75% Soap 16.50% nonionic surfactants 10.60% amphoteric surfactants 1.40% 1,2 propylene glycol 11.20% water ad 100%
- Powder detergent base (component B):
- Anionic surfactants Na-alkylbenzenesulfonate 15% Pentanatriumpyrophosphat 30% sodium 28% Optical brightener 0.1% carboxymethylcellulose 0.5% water glass 3.0% foam inhibitors 2.0% EDTA 0.2% Perfume 0.1% dye 0.7% Sodium sulfate and adjusting agents 17% water ad 100%
- component B 85 parts of component B were mixed with 15 parts of one Mixture consisting of 33.33% by weight of a silica (Sipernat 50, Degussa) and 66.66 wt .-% of a Talgamidoethylimidazoliniummethosulfats.
- the Textiles washed in a normal household washing machine.
- the detergent dosage was depending on the type of base different, but based on the usual Dosage recommendations for water hardness range II and normal dirty laundry.
- the laundry was dried statically (on the clothesline) and by means of a Test panels examined and evaluated.
- test panel After the terry towels have dried, they are cut into 10 individual lobes and stored in an air-conditioned room until they are finally evaluated by the test panel.
- the maximum rating is a result of 50.
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Silicon Polymers (AREA)
Description
cyclischen quaternären Polysiloxanen der allgemeinen Formel (IIa) und/oder
linearen quaternären Polysiloxanen der allgemeinen Formel (IIb) wobei
- M
- ein zweiwertiger Kohlenwasserstoffrest mit mindestens 4 Kohlenstoffatomen ist, der eine Hydroxylgruppe aufweist und der durch mindestens ein Sauerstoffatom unterbrochen sein kann, wobei das N-Atom des Restes Z mit dem Rest M über das zur C-OH-Gruppe im Rest M benachbarte Kohlenstoffatom verbunden ist,
- Z
- ein Rest ist,
- R1, R2, R3 =
- Alkylreste mit 1 bis 22 Kohlenstoffatomen oder Alkenylreste mit 2 bis 22 Kohlenstoffatomen, wobei die Alkyl- oder Alkenylreste Hydroxylgruppen aufweisen können und mindestens einer der Reste R1, R2, R3 mindestens 10 Kohlenstoffatome aufweist,
- R4, R5, R7, R9, R10 =
- Alkylreste mit 1 bis 22 Kohlenstoffatomen oder Alkenylreste mit 2 bis 22 Kohlenstoffatomen, wobei die Alkyl- oder Alkenylreste Hydroxylgruppen aufweisen können,
- R6 =
- -O- oder -NR8- Rest,
- R8 =
- Alkyl- oder Hydroxyalkylrest mit 1 bis 4 Kohlenstoffatomen oder Wasserstoffrest,
- x =
- 2 bis 4,
- n =
- eine Zahl von 0 bis 200,
- A-=
- ein anorganisches oder organisches Anion, das von einer üblichen physiologisch verträglichen Säure HA herrührt,
- Z1 =
- ein H-, OH-, ein Alkyl- oder Alkoxyrest ist, oder die Bedeutung eines Kohlenwasserstoffrestes mit mindestens 4 Kohlenstoffatomen hat, der eine oder mehrere Hydroxylgruppe(n) aufweist und durch ein oder mehrere Sauerstoffatome unterbrochen sein kann oder die Bedeutung des Restes hat,
- Z2 =
- die Gruppe bedeutet,
- Y =
- ein zweiwertiger Kohlenwasserstoffrest mit mindestens 2 Kohlenstoffatomen ist, der eine Hydroxylgruppe aufweisen und der durch mindestens ein Sauerstoff- oder Stickstoffatom unterbrochen sein kann,
- R11,R12,R13,R14 =
- gleich oder verschieden sind und Alkylreste mit 1 bis 4 Kohlenstoffatomen oder Benzylreste bedeuten oder jeweils R11 und R13 oder R12 und R14 Bestandteile eines verbrückenden Alkylenrestes sein können,
- R15 =
- ein Alkylrest mit 1 bis 20 Kohlenstoffatomen ist,
- m =
- ganze Zahl größer oder gleich 1 ist,
- n
- für eine Zahl im Bereich von 0 bis 150, insbesondere 5 bis 100,
- x
- für eine Zahl im Bereich von 2 bis 4,
- m
- für eine Zahl im Bereich von 1 bis 10, insbesondere 1 bis 5 steht.
als Builder werden Zeolithe, Polycarboxylate, Polyvinylpyrrolidone und amorphe wasserfreie Natriumsilicate und Schichtsilikate mitverwendet, wobei vielfach Citronensäure als Co-Builder zum Einsatz kommt;
Bestandteile der Bleichsysteme sind insbesondere Perborate und Natriumpercarbonat unter Mitverwendung von N-Acetyl-Verbindungen, N,N,N',N'-Tetraacetylethylendiamin oder p-Nonyloxybenzolsulfonat als Aktivatoren; als optische Aufheller kommen Stilbene und Distyrylbiphenyle und als Enzyme Proteasen, Amylasen, Cellulasen und zum Teil auch Lipasen zum Einsatz.
Bestandteil | Flüssig-Waschmittel [%] A | Pulver-Waschmittel [%] B |
Tenside | 20-50 | 10-15 |
Builder | 1-15 | 25-50 |
Co-Builder | 0-5 | 3-5 |
Bleichmittel | - | 10-25 |
Bleichmittel-aktivatoren | - | 1-3 |
Antiredepositations-additive | 0-1 | 0-1 |
Korrosionsinhibitoren | 2-6 | 2-6 |
Stabilisatoren | 0-1 | 0-1 |
Schauminhibitoren | - | 0,1-4,0 |
Enzyme | 0,5-2 | 0,3-0,8 |
Optischer Aufheller | 0,1-0,3 | 0,1-0,3 |
Soil Repellents | +/- | +/- |
Füllstoffe/Prozess-hilfe | - | 5-30 |
Wasser | ad 100 | ad 100 |
Anionische Tenside (Na-alkylbenzolsulfonat) | 21,75 % |
Seife | 16,50 % |
nichtionische Tenside | 10,60 % |
amphotere Tenside | 1,40 % |
1,2 Propylenglykol | 11,20 % |
Wasser | ad 100 % |
Anionische Tenside (Na-alkylbenzolsulfonat) | 15 % |
Pentanatriumpyrophosphat | 30 % |
Natriumperborat | 28 % |
Optischer Aufheller | 0,1 % |
Carboxymethylcellulose | 0,5 % |
Wasserglas | 3,0 % |
Schauminhibitoren | 2,0 % |
EDTA | 0,2 % |
Parfüm | 0,1 % |
Farbstoff | 0,7 % |
Natriumsulfat und Stellmittel | 17 % |
Wasser | ad 100 % |
(1) | Komponente A) | 95 % |
Formel (III) | 5 % | |
(2) | Komponente A) | 97,5 % |
Formel (III) | 3,5 % | |
(3) | Komponente B) | 97,5 % |
Formel (III) | 3,5 % | |
(4) | Komponente B) | 97,5 % |
Formel (V) | 3,5 % | |
(5) | Komponente A) | 95 % |
Formel (IV) | 5 % | |
(6) | Komponente A) | 97,5 % |
Formel (IV) | 2,5 % | |
(7) | Komponente B) | 97,5 % |
Formel (IV) | 2,5 % | |
(8) | Komponente B) | 97,5 % |
Formel (VI) | 2,5 % |
- Apparatur:
- Miele Waschmaschine W 715, W 719, W 918
- Prüfgewebe:
- Baumwollfrottiergewebe, Fa. Frottana, Fb. 901; 100 x 50 cm
- Ballastgewebe:
- glattes Baumwollgewebe
- Waschmittel:
- Flüssigwaschmittelbase (Komponente A) Pulverwaschmittelbase (Komponente B) Referenzwaschmittel (Ref):
- Dosiermenge:
- gemäß Dosierempfehlung für normal verschmutzte Wäsche
- Nachbehandlung:
- keine
- Trocknungsdauer:
- 24 Stunden unter klimatisierten Standardbedingungen
Claims (9)
- Verwendung von quaternären Polysiloxanen der allgemeinen Formel (I) und/oder
cyclischen quaternären Polysiloxanen der allgemeinen Formel (IIa) und/oder
linearen quaternären Polysiloxanen der allgemeinen Formel (IIb) wobei- M
- ein zweiwertiger Kohlenwasserstoffrest mit mindestens 4 Kohlenstoffatomen ist, der eine Hydroxylgruppe aufweist und der durch mindestens ein Sauerstoffatom unterbrochen sein kann, wobei das N-Atom des Restes Z mit dem Rest M über das zur C-OH-Gruppe im Rest M benachbarte Kohlenstoffatom verbunden ist,
- Z
- ein Rest ist,
- R1, R2, R3 =
- Alkylreste mit 1 bis 22 Kohlenstoffatomen oder Alkenylreste mit 2 bis 22 Kohlenstoffatomen, wobei die Alkyl- oder Alkenylreste Hydroxylgruppen aufweisen können und mindestens einer der Reste R1, R2, R3 mindestens 10 Kohlenstoffatome aufweist,
- R4, R5, R7, R9, R10 =
- Alkylreste mit 1 bis 22 Kohlenstoffatomen oder Alkenylreste mit 2 bis 22 Kohlenstoffatomen, wobei die Alkyl- oder Alkenylreste Hydroxylgruppen aufweisen können,
- R6 =
- -O- oder -NR8- Rest,
- R8 =
- Alkyl- oder Hydroxyalkylrest mit 1 bis 4 Kohlenstoffatomen oder Wasserstoffrest,
- x =
- 2 bis 4,
- n =
- eine Zahl von 0 bis 200,
- A-=
- ein anorganisches oder organisches Anion, das von einer üblichen physiologisch verträglichen Säure HA herrührt
- Z1 =
- ein H-, OH-, ein Alkyl- oder Alkoxyrest ist, oder die Bedeutung eines Kohlenwasserstoffrestes mit mindestens 4 Kohlenstoffatomen hat, der eine oder mehrere Hydroxylgruppe(n) aufweist und durch ein oder mehrere Sauerstoffatome unterbrochen sein kann oder die Bedeutung des Restes hat,
- Z2 =
- die Gruppe bedeutet,
- Y =
- ein zweiwertiger Kohlenwasserstoffrest mit mindestens 2 Kohlenstoffatomen ist, der eine Hydroxylgruppe aufweisen und der durch mindestens ein Sauerstoff- oder Stickstoffatom unterbrochen sein kann,
- R11,R12,R13,R14 =
- gleich oder verschieden sind und Alkylreste mit 1 bis 4 Kohlenstoffatomen oder Benzylreste bedeuten oder jeweils R11 und R13 oder R12 und R14 Bestandteile eines verbrückenden Alkylenrestes sein können,
- R15 =
- ein Alkylrest mit 1 bis 20 Kohlenstoffatomen ist,
- m =
- ganze Zahl größer oder gleich 1 ist
- Verwendung von quaternären Polysiloxanen der allgemeinen Formel (I) gemäß Anspruch 1, dadurch gekennzeichnet, dass
- n
- für eine Zahl im Bereich von 0 bis 150, insbesondere 5 bis 100,
- x
- für eine Zahl im Bereich von 2 bis 4
- Verwendung von quaternären Polysiloxanen der allgemeinen Formel (II a) und / oder Verwendung von quaternären Polysiloxanen der allgemeinen Formel (II b), gemäß Anspruch 1, dadurch gekennzeichnet, dass
- n
- für eine Zahl im Bereich von 0 bis 150, insbesondere 5 bis 100,
- x
- für eine Zahl im Bereich von 2 bis 4,
- m
- für eine Zahl im Bereich von 1 bis 10, insbesondere 1 bis 5
- Verwendung von quaternären Polysiloxanen nach den Ansprüchen 1 bis 5, dadurch gekennzeichnet, dass Y ein zweiwertiger Kohlenwasserstoffrest mit 3 bis 12 Kohlenstoffatomen ist.
- Anionische Waschmittel formulierungen mit weichmachender Wirkung, enthaltend eine wirksame Menge mindestens einer der Verbindungen der allgemeinen Formel (I) , (II a) oder (II b) gemäß Anspruch 1.
- Anionische Waschmittel formulierungen mit weichmachender Wirkung, enthaltend mindestens eine der Verbindungen der allgemeinen Formel (I), (II a) oder (II b) gemäß Anspruch 1 und mindestens ein festes Trägermaterial.
- Waschmittel mit weichmachender Wirkung gemäß Anspruch 8, dadurch gekennzeichnet, dass die festen Trägermaterialien ausgewählt sind aus der Gruppe der Kieselsäuren, Silicate, Natriumsilicate, Bentonite, Schichtsilicate, Zeolithe und Montmorillonite.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10051258A DE10051258A1 (de) | 2000-10-16 | 2000-10-16 | Verwendung von quaternären Polysiloxanen in Waschmittelformulierungen |
DE10051258 | 2000-10-16 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1199350A1 EP1199350A1 (de) | 2002-04-24 |
EP1199350B1 true EP1199350B1 (de) | 2003-04-02 |
Family
ID=7659978
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP01123706A Expired - Lifetime EP1199350B1 (de) | 2000-10-16 | 2001-10-04 | Verwendung von quaternären Polysiloxanen in Waschmittelformulierungen |
Country Status (9)
Country | Link |
---|---|
US (1) | US6706680B2 (de) |
EP (1) | EP1199350B1 (de) |
JP (1) | JP2002146682A (de) |
AT (1) | ATE236242T1 (de) |
AU (1) | AU6999301A (de) |
CA (1) | CA2355583C (de) |
DE (2) | DE10051258A1 (de) |
ES (1) | ES2194816T3 (de) |
PL (1) | PL199981B1 (de) |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6903061B2 (en) | 2000-08-28 | 2005-06-07 | The Procter & Gamble Company | Fabric care and perfume compositions and systems comprising cationic silicones and methods employing same |
US6818610B2 (en) | 2001-07-27 | 2004-11-16 | Procter & Gamble Company | Fabric care systems for providing anti-wrinkle benefits to fabric |
ATE284942T1 (de) | 2002-09-05 | 2005-01-15 | Procter & Gamble | Strukturierte flüssige weichmacherzusammensetzungen |
MXPA05004807A (es) * | 2002-11-04 | 2005-07-22 | Procter & Gamble | Composiciones para tratar telas, que comprenden diferentes siliconas, un proceso para prepararlas y metodo para utilizarlas. |
WO2004041986A1 (en) * | 2002-11-04 | 2004-05-21 | The Procter & Gamble Company | Fabric treatment compositions comprising oppositely charged polymers |
CA2504981A1 (en) * | 2002-11-04 | 2004-05-21 | Ge Bayer Silicones Gmbh & Co. Kg | Linear polyamino and/or polyammonium polysiloxane copolymers ii |
EP1565512B1 (de) * | 2002-11-04 | 2018-07-04 | Momentive Performance Materials GmbH | Lineare polyamino- und/oder polyammonium-polysiloxancopolymere i |
DE60316340T2 (de) | 2002-11-04 | 2008-06-12 | The Procter & Gamble Company, Cincinnati | Flüssige waschmittelzusammensetzung |
DE10259291B4 (de) * | 2002-12-18 | 2006-02-23 | Rudolf Gmbh & Co. Kg Chemische Fabrik | Hochkonzentrierte, selbstemulgierende Zubereitungen, enthaltend Organopolysiloxane und Alkylammoniumverbindungen und deren Verwendung in wässrigen Systemen |
US7179777B2 (en) * | 2002-12-23 | 2007-02-20 | Unilever Home & Personal Care Usa Division Of Conopco, Inc. | Laundry treatment compositions comprising a polymer with a cationic and polydialkylsiloxane moiety |
DE10316662A1 (de) | 2003-04-11 | 2004-11-11 | Ge Bayer Silicones Gmbh & Co. Kg | Reaktive Amino- und/oder Ammonium-Polysiloxanverbindungen |
US7622512B2 (en) * | 2005-12-21 | 2009-11-24 | Bausch & Lomb Incorporated | Cationic hydrophilic siloxanyl monomers |
US7759408B2 (en) * | 2005-12-21 | 2010-07-20 | Bausch & Lomb Incorporated | Silicon-containing monomers end-capped with polymerizable cationic hydrophilic groups |
US20070161769A1 (en) * | 2006-01-06 | 2007-07-12 | Schorzman Derek A | Polymerizable silicon-containing monomer bearing pendant cationic hydrophilic groups |
US7960447B2 (en) * | 2006-04-13 | 2011-06-14 | Bausch & Lomb Incorporated | Cationic end-capped siloxane prepolymer for reduced cross-link density |
US7468397B2 (en) * | 2006-06-30 | 2008-12-23 | Bausch & Lomb Incorporated | Polymerizable siloxane-quaternary amine copolymers |
US20080152540A1 (en) * | 2006-12-22 | 2008-06-26 | Bausch & Lomb Incorporated | Packaging solutions |
US7691917B2 (en) | 2007-06-14 | 2010-04-06 | Bausch & Lomb Incorporated | Silcone-containing prepolymers |
US8268975B2 (en) | 2009-04-03 | 2012-09-18 | Dow Agrosciences Llc | Demulsification compositions, systems and methods for demulsifying and separating aqueous emulsions |
US9540489B2 (en) * | 2013-07-29 | 2017-01-10 | The Procter & Gamble Company | Blocky cationic organopolysiloxane |
DE102013219046A1 (de) | 2013-09-23 | 2015-03-26 | Rudolf Gmbh | Polysiloxane mit quaternierten heterocyclischen Gruppen |
EP3360917A1 (de) * | 2017-02-14 | 2018-08-15 | CHT R. BEITLICH GmbH | Bodenkonditionierer für die reduzierung der sodizität und dispersion zur verbesserung der wassermobilität in verschiedenen böden |
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US3624120A (en) * | 1969-12-22 | 1971-11-30 | Procter & Gamble | Quaternary ammonium salts of cyclic siloxane polymers |
LU84463A1 (fr) * | 1982-11-10 | 1984-06-13 | Oreal | Polymeres polysiloxanes polyquaternaires |
DE3402698A1 (de) | 1984-01-26 | 1985-08-08 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von fuellstoffhaltigen polyurethan (harnstoff)-massen, fuellstoffhaltige polyurethan(harnstoff)-massen und ihre verwendung |
DE3705121A1 (de) * | 1987-02-18 | 1988-09-01 | Goldschmidt Ag Th | Polyquaternaere polysiloxan-polymere, deren herstellung und verwendung in kosmetischen zubereitungen |
DE3719086C1 (de) * | 1987-06-06 | 1988-10-27 | Goldschmidt Ag Th | Diquartaere Polysiloxane,deren Herstellung und Verwendung in kosmetischen Zubereitungen |
DE4443062C2 (de) * | 1994-12-03 | 1997-07-17 | Wella Ag | Mittel und Verfahren zur dauerhaften Haarverformung |
US5707435A (en) * | 1996-10-16 | 1998-01-13 | Dow Corning Corporation | Ammonium siloxane emulsions and their use as fiber treatment agents |
DE19852621A1 (de) * | 1998-11-14 | 2000-05-18 | Hansa Textilchemie Gmbh | Permanentes Mittel zum Ausrüsten von Fasern oder aus Faser bestehenden Produkten |
DE19853720A1 (de) * | 1998-11-20 | 2000-05-25 | Henkel Kgaa | Allzweckreiniger mit diquaternärem-Polysiloxan |
DE19944416A1 (de) * | 1999-09-16 | 2001-03-22 | Henkel Kgaa | Klarspülmittel |
-
2000
- 2000-10-16 DE DE10051258A patent/DE10051258A1/de not_active Withdrawn
-
2001
- 2001-08-20 CA CA002355583A patent/CA2355583C/en not_active Expired - Lifetime
- 2001-09-11 AU AU69993/01A patent/AU6999301A/en not_active Abandoned
- 2001-10-04 DE DE50100137T patent/DE50100137D1/de not_active Expired - Lifetime
- 2001-10-04 AT AT01123706T patent/ATE236242T1/de not_active IP Right Cessation
- 2001-10-04 ES ES01123706T patent/ES2194816T3/es not_active Expired - Lifetime
- 2001-10-04 EP EP01123706A patent/EP1199350B1/de not_active Expired - Lifetime
- 2001-10-05 US US09/971,556 patent/US6706680B2/en not_active Expired - Lifetime
- 2001-10-15 PL PL350121A patent/PL199981B1/pl unknown
- 2001-10-16 JP JP2001318402A patent/JP2002146682A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
ATE236242T1 (de) | 2003-04-15 |
JP2002146682A (ja) | 2002-05-22 |
EP1199350A1 (de) | 2002-04-24 |
US6706680B2 (en) | 2004-03-16 |
CA2355583A1 (en) | 2002-04-16 |
PL350121A1 (en) | 2002-04-22 |
ES2194816T3 (es) | 2003-12-01 |
DE50100137D1 (de) | 2003-05-08 |
DE10051258A1 (de) | 2002-04-25 |
CA2355583C (en) | 2009-10-20 |
US20020068689A1 (en) | 2002-06-06 |
PL199981B1 (pl) | 2008-11-28 |
AU6999301A (en) | 2002-05-23 |
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