WO2000058429A1 - Use of an alkyl polyglycoside to enhance the performance of a cationic fabric care product - Google Patents
Use of an alkyl polyglycoside to enhance the performance of a cationic fabric care product Download PDFInfo
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- WO2000058429A1 WO2000058429A1 PCT/US2000/006425 US0006425W WO0058429A1 WO 2000058429 A1 WO2000058429 A1 WO 2000058429A1 US 0006425 W US0006425 W US 0006425W WO 0058429 A1 WO0058429 A1 WO 0058429A1
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- alkyl polyglycoside
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Classifications
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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
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
-
- 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
- C11D1/66—Non-ionic compounds
- C11D1/835—Mixtures of non-ionic with cationic compounds
-
- 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
-
- 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
- C11D1/66—Non-ionic compounds
- C11D1/662—Carbohydrates or derivatives
Definitions
- Cationic surfactants are widely used in acidic aqueous and nonaqueous systems as textile softeners, dispersants, errtulsifiers, wetting agents, sanitizers, dye-fixing agents, foam stabilizers and corrosion inhibitors. To some extent, the usage pattern mirrors that of anionic surfactants in neutral and alkaline solutions .
- Positively charged cationic surfactants are adsorbed more strongly than nonionic surfactants on a variety of substrates including textiles, metals, glass, plastics, minerals and animal and human tissue, all of which often carry a negative surface charge.
- the substantivity of cationic surfactants is the key property in many applications in which they are uniquely effective.
- the quaternary ammonium ion is a much stronger hydrophile than a primary, secondary or tertiary a ino group and is strong enough to carry into solution a hydrophobe in the surfactant molecular weight range, even in alkaline media.
- the discreet positive charge on the quaternary ammonium ion promotes strong adsorption on negatively charged substrates, such as fabrics, and is the basis for the wide-spread use of the surfactants in domestic fabric-softening compositions.
- the present invention is directed to a softening and antistatic composition containing: (a) an alkyl polyglycoside corresponding to formula
- RjOdljO Z (I) wherein R x is a monovalent organic radical having from about 6 to about 30 carbon atoms; R 2 is a divalent alkylene radical having from 2 to 4 carbon atoms; Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a value from 0 to about 12; a is a number having a value from 1 to about 6 ; and
- R 3 CO-O- -0-COR 3 [R 3 CO-O- -0-COR 3 ]X (II) wherein R 3 CO is an aliphatic acyl radical containing from about 12 to about 22 carbon atoms and up to 3 double bonds, n is 2 or 3, and X is a halide, methosulfate or methophosphate ion, and wherein (a) and (b) are present in the composition in a ratio by weight of from about 1:3 to about 1:10.
- the present invention is also directed to a process for increasing the softening and antistatic properties of an ester quat involving:
- alkyl polyglycosides which can be used in the invention are those corresponding to formula I :
- Preferred alkyl polyglycosides which can be used in the compositions according to the invention have the formula I wherein Z is a glucose residue and b is zero.
- alkyl polyglycosides are commercially available, for example, as APG®, GLUCOPON®, PLANTAREN® or AGRIMUL® surfactants from Henkel Corporation, Ambler, PA, 19002.
- surfactants include but are not limited to:
- GLUCOPON® 220 Surfactant - an alkyl polyglycoside in which the alkyl group contains 8 to 10 carbon atoms and having an average degree of polymerization of 1.5.
- GLUCOPON® 225 Surfactant - an alkyl polyglycoside in which the alkyl group contains 8 to 10 carbon atoms and having an average degree of polymerization of 1.7.
- GLUCOPON® 600 Surfactant - an alkyl polyglycoside in which the alkyl group contains 12 to 16 carbon atoms and having an average degree of polymerization of 1.4.
- GLUCOPON® 625 Surfactant - an alkyl polyglycoside in which the alkyl group contains 12 to 16 carbon atoms and having an average degree of polymerization of 1.4.
- APG® 325 Surfactant - an alkyl polyglycoside in which the alkyl group contains 9 to 11 carbon atoms and having an average degree of polymerization of 1.6.
- PLANTAREN® 2000 Surfactant - an alkyl polyglycoside in which the alkyl group contains 8 to 16 carbon atoms and having an average degree of polymerization of 1.4.
- PLANTAREN® 1300 Surfactant - an alkyl polyglycoside in which the alkyl group contains 12 to 16 carbon atoms and having an average degree of polymerization of 1.6.
- AGRIMUL® PG 2067 Surfactant - an alkyl polyglycoside in which the alkyl group contains 8 to 10 carbon atoms and having an average degree of polymerization of 1.7.
- alkyl polyglycoside surfactant compositions which are comprised of mixtures of compounds of formula I as described in U.S. patents
- a particularly preferred alkyl polyglycoside for use in the present invention is one corresponding to formula
- R x is a monovalent organic radical having from about 8 to about 16 carbon atoms, b is zero, and a is a number having a value of from about 1 to about 2.
- Ester quats are understood as being technical quaternized difatty acid trialkanolamine ester salts which may be obtained by the relevant methods of preparative organic chemistry. Methods of their preparation include the esterification of fatty acids with a trialkanolamine such as triethanolamine or tripropanolamine . The difatty acid ester thus formed can then be quaternized in known manner with, for example, methyl chloride or dimethyl sulfate.
- Suitable fatty acids from which the ester quats may be derived include, but are not limited to, caprioc acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, elaidic acid, petroselic acid, linoleic acid, linolenic acid, arachic acid, gadoleic acid, behenic acid and erucic acid, as well as technical mixtures thereof such as, for example, the hydrogenation of vegetable oils or animal fats.
- ester quats which can be used in the present invention are those corresponding to formula II:
- a softening and antistatic composition containing:
- R 3 CO-0- (CH 2 ) -0-COR 3 [R 3 CO-0- (CH 2 ) -0-COR 3 ]X ⁇ (II) wherein R 3 C0 is an aliphatic acyl radical containing from about 12 to about 22 carbon atoms and up to 3 double bonds, n is 2 or 3, and X is a halide, methosulfate or methophosphate ion, and wherein (a) and (b) are present in the composition in a ratio by weight of from about 1:3 to about 1:10, preferably from about 1:4 to about 1:6, and most preferably about 1:5.
- the above-disclosed softening and antistatic composition may be employed in a variety of cleaning compositions such as powdered or liquid light-duty and heavy-duty laundry detergents, personal cleansing compositions, hard surface cleaners, fabric softening agents, and the like.
- cleaning compositions such as powdered or liquid light-duty and heavy-duty laundry detergents, personal cleansing compositions, hard surface cleaners, fabric softening agents, and the like.
- the precise amount of softening and antistatic composition present in each cleaning composition will be determined by the formulator, depending on the product's application.
- a process for increasing the softening and antistatic properties of an ester quat involving: (a) providing an alkyl polyglycoside corresponding to formula I: R 1 0(R 2 0) b (Z) a (I) wherein R ⁇ is a monovalent organic radical having from about 6 to about 30 carbon atoms; R 2 is a divalent alkylene radical having from 2 to 4 carbon atoms; Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a value from 0 to about 12; a is a number having a value from 1 to about 6; (b) providing an ester quat corresponding to formula II :
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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)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Detergent Compositions (AREA)
Abstract
A softening and antistatic composition containing: (a) an alkyl polyglycoside; and (b) an ester quat, wherein (a) and (b) are present in the composition in a ratio by weight of from about 1:3 to about 1:10.
Description
USE OF AN ALKYL POLYGLYCOSIDE TO ENHANCE THE PERFORMANCE OF A CATIONIC FABRIC CARE PRODUCT
BACKGROUND OF THE INVENTION:
Cationic surfactants are widely used in acidic aqueous and nonaqueous systems as textile softeners, dispersants, errtulsifiers, wetting agents, sanitizers, dye-fixing agents, foam stabilizers and corrosion inhibitors. To some extent, the usage pattern mirrors that of anionic surfactants in neutral and alkaline solutions .
Positively charged cationic surfactants are adsorbed more strongly than nonionic surfactants on a variety of substrates including textiles, metals, glass, plastics, minerals and animal and human tissue, all of which often carry a negative surface charge. The substantivity of cationic surfactants is the key property in many applications in which they are uniquely effective. The quaternary ammonium ion is a much stronger hydrophile than a primary, secondary or tertiary a ino group and is strong enough to carry into solution a hydrophobe in the surfactant molecular weight range, even in alkaline media. The discreet positive charge on the quaternary ammonium ion promotes strong adsorption on negatively charged substrates, such as fabrics, and is the basis for the wide-spread use of the surfactants in domestic fabric-softening compositions.
While the use of cationic surfactants has been shown
to impart adequate softening and antistatic properties onto textile substrates treated therewith, there in a continuing need to further increase the effectiveness of these compounds .
BRIEF SUMMARY OF THE INVENTION: The present invention is directed to a softening and antistatic composition containing: (a) an alkyl polyglycoside corresponding to formula
I:
RjOdljO Z), (I) wherein Rx is a monovalent organic radical having from about 6 to about 30 carbon atoms; R2 is a divalent alkylene radical having from 2 to 4 carbon atoms; Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a value from 0 to about 12; a is a number having a value from 1 to about 6 ; and
(b) an ester quat corresponding to formula II:
[R3CO-O- -0-COR3]X (II)
wherein R3CO is an aliphatic acyl radical containing from about 12 to about 22 carbon atoms and up to 3 double bonds, n is 2 or 3, and X is a halide, methosulfate or methophosphate ion, and wherein (a) and (b) are present in the composition in a ratio by weight of from about 1:3 to about 1:10.
The present invention is also directed to a process
for increasing the softening and antistatic properties of an ester quat involving:
(a) providing an alkyl polygiycoside corresponding to formula I :
R10(R20)b(Z)a (I) wherein Rx is a monovalent organic radical having from about 6 to about 30 carbon atoms; R2 is a divalent alkylene radical having from 2 to 4 carbon atoms; Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a value from 0 to about 12; a is a number having a value from 1 to about 6 ;
(b) providing an ester quat corresponding to formula II: CH3
[R3CO-0-(CH2)n-N+-(CH2)n-0-COR3]X" (II)
[CH2 -OH wherein R3CO is an aliphatic acyl radical containing from about 12 to about 22 carbon atoms and up to 3 double bonds, n is 2 or 3, and X is a halide, methosulfate or methophosphate ion; and (c) combining (a) and (b) in a ratio by weight of from about 1:3 to about 1:10.
DETAILED DESCRIPTION OF THE INVENTION:
Other than in the operating examples, or where otherwise indicated, all numbers expressing quantities of ingredients and reaction conditions are to be understood as being modified in all instances by the term "about".
The present invention is directed to the surprising discovery that by combining an ester quat with an alkyl polyglycoside, in a specific ratio by weight, a synergistic increase in softening and antistatic properties of the ester quat is realized.
The alkyl polyglycosides which can be used in the invention are those corresponding to formula I :
R10(R20)b(Z)a (I) wherein Rx is a monovalent organic radical having from about 6 to about 30 carbon atoms; R2 is a divalent alkylene radical having from 2 to 4 carbon atoms; Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a value from 0 to about 12; a is a number having a value from 1 to about 6. Preferred alkyl polyglycosides which can be used in the compositions according to the invention have the formula I wherein Z is a glucose residue and b is zero. Such alkyl polyglycosides are commercially available, for example, as APG®, GLUCOPON®, PLANTAREN® or AGRIMUL® surfactants from Henkel Corporation, Ambler, PA, 19002. Examples of such surfactants include but are not limited to:
1. GLUCOPON® 220 Surfactant - an alkyl polyglycoside in which the alkyl group contains 8 to 10 carbon atoms and having an average degree of polymerization of 1.5.
2. GLUCOPON® 225 Surfactant - an alkyl polyglycoside in which the alkyl group contains 8 to 10 carbon atoms and having an average degree of polymerization of 1.7.
3. GLUCOPON® 600 Surfactant - an alkyl polyglycoside in
which the alkyl group contains 12 to 16 carbon atoms and having an average degree of polymerization of 1.4.
4. GLUCOPON® 625 Surfactant - an alkyl polyglycoside in which the alkyl group contains 12 to 16 carbon atoms and having an average degree of polymerization of 1.4.
5. APG® 325 Surfactant - an alkyl polyglycoside in which the alkyl group contains 9 to 11 carbon atoms and having an average degree of polymerization of 1.6. 6. PLANTAREN® 2000 Surfactant - an alkyl polyglycoside in which the alkyl group contains 8 to 16 carbon atoms and having an average degree of polymerization of 1.4.
7. PLANTAREN® 1300 Surfactant - an alkyl polyglycoside in which the alkyl group contains 12 to 16 carbon atoms and having an average degree of polymerization of 1.6.
8. AGRIMUL® PG 2067 Surfactant - an alkyl polyglycoside in which the alkyl group contains 8 to 10 carbon atoms and having an average degree of polymerization of 1.7.
Other examples include alkyl polyglycoside surfactant compositions which are comprised of mixtures of compounds of formula I as described in U.S. patents
5,266,690 and 5,449,763, the entire contents of both of which are incorporated herein by reference.
A particularly preferred alkyl polyglycoside for use in the present invention is one corresponding to formula
I wherein Rx is a monovalent organic radical having from about 8 to about 16 carbon atoms, b is zero, and a is a number having a value of from about 1 to about 2.
Ester quats are understood as being technical
quaternized difatty acid trialkanolamine ester salts which may be obtained by the relevant methods of preparative organic chemistry. Methods of their preparation include the esterification of fatty acids with a trialkanolamine such as triethanolamine or tripropanolamine . The difatty acid ester thus formed can then be quaternized in known manner with, for example, methyl chloride or dimethyl sulfate. Examples of suitable fatty acids from which the ester quats may be derived include, but are not limited to, caprioc acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, elaidic acid, petroselic acid, linoleic acid, linolenic acid, arachic acid, gadoleic acid, behenic acid and erucic acid, as well as technical mixtures thereof such as, for example, the hydrogenation of vegetable oils or animal fats.
The ester quats which can be used in the present invention are those corresponding to formula II:
[R3CO-0- (CH2) COR3] X" (II)
wherein R3CO is an aliphatic acyl radical containing from about 12 to about 22 carbon atoms and up to 3 double bonds, n is 2 or 3, and X is a halide, methosulfate or methophosphate ion.
According to one embodiment of the present
invention, there is provided a softening and antistatic composition containing:
(a) an alkyl polyglycoside corresponding to formula I:
R10(R20)b(Z)a (I) wherein Rλ is a monovalent organic radical having from about 6 to about 30 carbon atoms; R2 is a divalent alkylene radical having from 2 to 4 carbon atoms; Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a value from 0 to about 12; a is a number having a value from 1 to about 6 ; and
(b) an ester quat corresponding to formula II:
[R3CO-0- (CH2) -0-COR3]X~ (II)
wherein R3C0 is an aliphatic acyl radical containing from about 12 to about 22 carbon atoms and up to 3 double bonds, n is 2 or 3, and X is a halide, methosulfate or methophosphate ion, and wherein (a) and (b) are present in the composition in a ratio by weight of from about 1:3 to about 1:10, preferably from about 1:4 to about 1:6, and most preferably about 1:5.
The above-disclosed softening and antistatic composition may be employed in a variety of cleaning compositions such as powdered or liquid light-duty and heavy-duty laundry detergents, personal cleansing compositions, hard surface cleaners, fabric softening agents, and the like. The precise amount of softening
and antistatic composition present in each cleaning composition will be determined by the formulator, depending on the product's application. According to another embodiment of the present invention, there is also provided a process for increasing the softening and antistatic properties of an ester quat involving: (a) providing an alkyl polyglycoside corresponding to formula I: R10(R20)b(Z)a (I) wherein Rλ is a monovalent organic radical having from about 6 to about 30 carbon atoms; R2 is a divalent alkylene radical having from 2 to 4 carbon atoms; Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a value from 0 to about 12; a is a number having a value from 1 to about 6; (b) providing an ester quat corresponding to formula II :
[R3C0-0- (CH2) -0-C0R3]X~ (II)
wherein R3C0 is an aliphatic acyl radical containing from about 12 to about 22 carbon atoms and up to 3 double bonds, n is 2 or 3, and X is a halide, methosulfate or methophosphate ion; and (c) combining (a) and (b) in a ratio by weight of from about 1:3 to about 1:10, preferably from about 1:4 to about 1:6, and most preferably about 1:5.
The present invention will be better understood from the examples which follow, all of which are intended for
illustrative purposes only, and are not meant to unduly limit the scope of the invention in any way.
EXAMPLES Cotton towels were rinsed in a solution of esterquat, and a mixture of esterquat and alkyl polyglycoside. A panel of 25 panelists judged towels rinsed in both solutions, for softness. The towels rinsed in the esterquat/alkyl polyglycoside solution were judged to be softer by approximately 80% of the panelists, as compared to those towels rinsed in esterquat alone.
The towels were then tested to determine their static using a Faraday Cage. Those towels rinsed in esterquat alone were found to reduce about 80% static. However, those towels rinsed in the esterquat/alkyl polyglycoside mixture were found to reduce about 90% static .
Hence, it is surprisingly seen that by employing a mixture of esterquat and alkyl polyglycoside, in the disclosed ratios by weight, significant improvement in both softness and static reduction is realized.
Claims
1. A softening and antistatic composition comprising:
(a) an alkyl polyglycoside corresponding to formula I:
R10(R20)b(Z)a (I) wherein Rλ is a monovalent organic radical having from about 6 to about 30 carbon atoms; R2 is a divalent alkylene radical having from 2 to 4 carbon atoms; Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a value from 0 to about 12; a is a number having a value from 1 to about 6 ; and
(b) an ester quat corresponding to formula II:
[R3C0-0- (CH2 -0-COR3]X~ (II)
2. The composition of claim 1 wherein in formula I, Rx is a monovalent organic radical having from about 8 to about 16 carbon atoms, b is zero, and a is a number having a value of from about 1 to about 2.
3. The composition of claim 1 wherein (a) and (b) are present in the composition in a ratio by weight of about 1:5.
4. A process for increasing softening and antistatic properties of an ester quat involving:
(a) providing an alkyl polyglycoside corresponding to formula I :
R10(R20)b(Z)a (I) wherein Rλ is a monovalent organic radical having from about 6 to about 30 carbon atoms; R2 is a divalent alkylene radical having from 2 to 4 carbon atoms; Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a value from 0 to about 12; a is a number having a value from 1 to about 6 ;
(b) providing an ester quat corresponding to formula II:
[R3C0-0- (CH2 -0-COR3]X" (II)
5. The process of claim 4 wherein in formula I, Rλ is a monovalent organic radical having from about 8 to about 16 carbon atoms, b is zero, and a is a number having a value of from about 1 to about 2.
6. The process of claim 4 wherein (a) and (b) are present in the composition in a ratio by weight of about 1:5.
7. A cleaning composition containing the softening and antistatic composition of claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU37397/00A AU3739700A (en) | 1999-03-26 | 2000-03-23 | Use of an alkyl polyglycoside to enhance the performance of a cationic fabric care product |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27739799A | 1999-03-26 | 1999-03-26 | |
| US09/277,397 | 1999-03-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2000058429A1 true WO2000058429A1 (en) | 2000-10-05 |
Family
ID=23060689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2000/006425 Ceased WO2000058429A1 (en) | 1999-03-26 | 2000-03-23 | Use of an alkyl polyglycoside to enhance the performance of a cationic fabric care product |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU3739700A (en) |
| WO (1) | WO2000058429A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002051971A1 (en) * | 2000-12-22 | 2002-07-04 | Kao Corporation, S.A. | Fiber softening compositions containing non-ionic surface active agents |
| FR2869912A1 (en) * | 2004-05-04 | 2005-11-11 | Agro Ind Rech S Et Dev A R D S | NOVEL FAMILY OF COMPOSITIONS BASED ON ALKYL POLYGLYCOSIDES AND COMPOUNDS DERIVED FROM GLYCINE BETAINE, USE AS A SURFACE AGENT |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5627144A (en) * | 1992-09-11 | 1997-05-06 | Henkel Kommanditgesellschaft Auf Aktien | Composition for enhanced crude oil recovery operations containing hydrochloric acid or hydrofluoric acid, or mixtures thereof with ester quaternary ammonium compounds or/and alkyl quaternary ammonium compounds |
| DE19629666A1 (en) * | 1996-07-23 | 1998-01-29 | Henkel Kgaa | Process for the hydrophilic finishing of fibers or nonwovens |
| EP0872541A2 (en) * | 1997-04-16 | 1998-10-21 | Henkel Kommanditgesellschaft auf Aktien | Liquid detergent for delicate textiles in the form of a microemulsion |
-
2000
- 2000-03-23 WO PCT/US2000/006425 patent/WO2000058429A1/en not_active Ceased
- 2000-03-23 AU AU37397/00A patent/AU3739700A/en not_active Abandoned
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5627144A (en) * | 1992-09-11 | 1997-05-06 | Henkel Kommanditgesellschaft Auf Aktien | Composition for enhanced crude oil recovery operations containing hydrochloric acid or hydrofluoric acid, or mixtures thereof with ester quaternary ammonium compounds or/and alkyl quaternary ammonium compounds |
| DE19629666A1 (en) * | 1996-07-23 | 1998-01-29 | Henkel Kgaa | Process for the hydrophilic finishing of fibers or nonwovens |
| EP0872541A2 (en) * | 1997-04-16 | 1998-10-21 | Henkel Kommanditgesellschaft auf Aktien | Liquid detergent for delicate textiles in the form of a microemulsion |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002051971A1 (en) * | 2000-12-22 | 2002-07-04 | Kao Corporation, S.A. | Fiber softening compositions containing non-ionic surface active agents |
| ES2179757A1 (en) * | 2000-12-22 | 2003-01-16 | Kao Corp Sa | Fiber softening compositions containing non-ionic surface active agents |
| US6890895B2 (en) | 2000-12-22 | 2005-05-10 | Kao Corporation S.A. | Fiber-softening compositions containing non-ionic surfactants |
| FR2869912A1 (en) * | 2004-05-04 | 2005-11-11 | Agro Ind Rech S Et Dev A R D S | NOVEL FAMILY OF COMPOSITIONS BASED ON ALKYL POLYGLYCOSIDES AND COMPOUNDS DERIVED FROM GLYCINE BETAINE, USE AS A SURFACE AGENT |
| WO2005121294A1 (en) * | 2004-05-04 | 2005-12-22 | Agro Industrie Recherches Et Developpements (A.R.D.) | Novel family of alkyl polyglycoside compositions and compounds derived from glycine betain, use as surfactant |
Also Published As
| Publication number | Publication date |
|---|---|
| AU3739700A (en) | 2000-10-16 |
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