WO1994004641A1 - Fabric conditioning composition - Google Patents

Fabric conditioning composition Download PDF

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Publication number
WO1994004641A1
WO1994004641A1 PCT/US1993/007608 US9307608W WO9404641A1 WO 1994004641 A1 WO1994004641 A1 WO 1994004641A1 US 9307608 W US9307608 W US 9307608W WO 9404641 A1 WO9404641 A1 WO 9404641A1
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WO
WIPO (PCT)
Prior art keywords
acid
fabric conditioning
conditioning composition
weight
alkanolamine
Prior art date
Application number
PCT/US1993/007608
Other languages
French (fr)
Inventor
Subhash Harmalker
Jean-Paul Grandmaire
Viviane Tack
Alain Jacques
Original Assignee
Colgate-Palmolive Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US07/934,097 external-priority patent/US5288847A/en
Application filed by Colgate-Palmolive Company filed Critical Colgate-Palmolive Company
Priority to EP93920019A priority Critical patent/EP0656934A1/en
Publication of WO1994004641A1 publication Critical patent/WO1994004641A1/en

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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
    • C11D1/46—Esters of carboxylic acids with amino alcohols; Esters of amino carboxylic acids with alcohols
    • 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
    • C11D1/645—Mixtures of compounds all of which are cationic
    • 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
    • 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
    • C11D3/0015—Softening compositions liquid

Definitions

  • This invention relates to fabric conditioning compositions which are suitable for softening in the rinse cycle of an automatic household washing machine, and which are especially adapted for use under European laundering conditions. More particularly, the present invention relates to fabric conditioning compositions comprising defined alkanolamine diester and/or triester combination with an acid and optionally a fatty alcohol, which compositions are characterized by superior environmental compatibility relative to conventional tertiary amine or quaternary ammonium fabric softening compositions concomitant with providing improved calcium salt solubilization and reduction of encrustation on treated fabrics.
  • the combination of organic acid with cationic fabric softener such as amines and quaternary ammonium compounds is extensively disclosed in the prior art.
  • 3,904,359 and 3,954,630 to Ramachandran disclose a fabric treating composition
  • a fabric treating composition comprising a complexing acid such as citric or maleic acid in combination with a quaternary ammonium compound or amines such as primary tallow and primary coco amine.
  • the function of the acid is to prevent yellowing of fabrics due to build-up of cationic softener and to provide a complexing site for metal ions contained in soils.
  • European Patent Publication No. 123,400 to Kardouch discloses detergent compositions containing salts of specified tertiary amines and carboxylic acids which are utilized in the form of modules that pass virtually unchanged through the wash and rinse and then condition the fabric when heated in a dryer.
  • European Patent Publication No. 417,987 describes fabric softening compositions comprised of tertiary amines and carboxylic acids.
  • the present invention provides environmentally compatible and biodegradable rinse cycle fabric conditioning compositions capable of providing improved softening with significant reduction and solubilization of unwanted mineral encrustations on fabrics to be softened, such encrustations having been generally deposited on the fabrics during the course of prior laundering in water having a high mineral content, which comprises a fabric conditioning mixture of:
  • R 1f R 2 and R 3 are each independently hydrogenated tallow or soft tallow; and n, m and p are integers from 1 to 4; and (b) unreacted organic acid or mineral acid.
  • the fabric softening composition further contains from about 0.2 to about 5%, by weight, preferably from about 0.5 to about 3%, and most preferably from about 0.5 to 1%, by weight, of a fatty alcohol having from about 10 to about 24 carbon atoms.
  • the integers n, m and p in the general formula are 2, and R 1 t R 2 and R 3 are hydrogenated tallow to provide a triethanolamine diester and/or triester.
  • the invention also encompasses a method for softening fabrics and removing unwanted mineral encrustations therefrom comprising rinsing the fabrics to be treated in an aqueous bath containing an effective amount of a composition comprised of the above-defined fabric conditioning mixture.
  • the present invention is predicated on the discovery that the combination of alkanol amine diester and/or triester fabric softener as defined above with an organic or mineral acid provides a biodegradable softener which has the capability of removing mineral encrustations such as calcium and magnesium salts, and in particular, phosphates and carbonates of calcium and magnesium, which cumulatively deposit on the fabrics during the course of prior laundering in hard water, i.e. water having a mineral content above about 300 ppm, conditions generally associated with European laundering conditions.
  • a particularly preferred softening compound as described herein comprises a mixture of triethanolamine diester and triester sold by Hoechst Company under the trade designation of E 91/526 acid E 91/516.
  • compositions of the present invention are environmentally compatible and biodegradable rinse cycle fabric conditioning compositions which contain as the active fabric softening compound an alkanolamine diester and/or triester as defined above.
  • the use of such fabric softening compound avoids the more traditional di-long chain, di-short chain quaternary ammonium softeners which are used extensively in commercial rinse cycle softeners, but which presently have become the focus of increasing legislative concerns, particularly in Europe, because of their lack of biodegradability in aqueous effluent streams.
  • the total amount of diester and triester amine in the total composition is from about 1 to 20%, by weight, preferably from about 2 to 10%, by weight.
  • the second essential ingredient of the fabric conditioning composition is the acid which has a dual function, depending on the acid concentration.
  • the first function is preventive in nature and occurs when the acid in the diluted rinse cycle solution is present in sufficient amount to react with the insoluble salts of the water hardness ions (calcium and magnesium) to form soluble acid salts and to remove any mineral salts which may have deposited on fabrics during the washing step of the wash cycle.
  • the second function is more curative in nature and refers to the removal of mineral encrustations which have been cumulatively deposited during prior washing throughout the fabric's life.
  • a dosage of 110 to 150 ml of softening composition is typical for use in the rinse cycle; the water hardness varies from about 200 to 400 ppm, most typically about 300 ppm.
  • an acid concentration of from about 5 to about 25%, by weight, preferably from about 8 to 25%, by weight is required in the fabric softening composition.
  • the acid used may be an organic or mineral acid.
  • the organic acids are preferably saturated or unsaturated C2-C ⁇ carboxylic acids such as citric acid, formic acid, maleic acid, tartaric acid and succinic acid. Citric acid, malonic acid and maleic acid are particularly preferred.
  • a mineral acid, such as HCI, which is particularly effective to protonate the diester amine softening compound, may be advantageously combined with such organic acid, the amount of acid used in excess of protonation being referred to herein as "unreacted". Generally, the concentration of unreacted mineral acid should not exceed about 5%, preferably not more than 2%, by weight, of the fabric conditioning composition so as to prevent unwanted product separation.
  • a carboxylic acid may then be used to supplement the mineral acid up to a total acid content of about 25% without adversely affecting product stability.
  • An optional fabric conditioning ingredient is a fatty alcohol wherein the hydrophobic group may be a straight or branched chain alkyl or alkenyl group having from about 10 to 24, preferably from about 10 to 20, especially preferably from about 12 to 20 carbon atoms.
  • the fatty alcohol include decanol, dodecanol, tetradecanol, pentadecanol, hexadecanol, octadecanol, lauryl alcohol, palmityl alcohol, stearyl alcohol, oleyl alcohol, and mixtures thereof.
  • the fatty alcohol may be of natural or synthetic origin and my include, for example, mixed alcohol, such as C ⁇ 6 -C 18 alcohols prepared by Ziegler polymerization of ethylene.
  • the fatty alcohol may be present in the composition in a minor amount relative to the cationic fabric softener such that the ratio, by weight, of the cationic fabric softener to fatty alcohol is in the range of from about 6:1 to 2:1 , preferably about 5:1 to 3:1, and most preferably about 4:1.

Abstract

An environmentally compatible and biodegradable fabric conditioning composition is provided capable of providing improved softening with significant reduction and solubilization of unwanted mineral encrustations on fabrics to be softened. The composition comprises a fabric conditioning mixture of (a) at least one of (i) an alkanolamine diester having general formula (I) and (ii) an alkanolamine triester having general formula (II) wherein R1, R2 and R3 are each independently hydrogenated tallow or soft tallow; and n,m and p are integers from 1 to 4.

Description

FABRIC CONDITIONING COMPOSITION
BACKGROUND OF THE INVENTION
This invention relates to fabric conditioning compositions which are suitable for softening in the rinse cycle of an automatic household washing machine, and which are especially adapted for use under European laundering conditions. More particularly, the present invention relates to fabric conditioning compositions comprising defined alkanolamine diester and/or triester combination with an acid and optionally a fatty alcohol, which compositions are characterized by superior environmental compatibility relative to conventional tertiary amine or quaternary ammonium fabric softening compositions concomitant with providing improved calcium salt solubilization and reduction of encrustation on treated fabrics. The combination of organic acid with cationic fabric softener such as amines and quaternary ammonium compounds is extensively disclosed in the prior art. U.S. Patent Nos. 3,904,359 and 3,954,630 to Ramachandran disclose a fabric treating composition comprising a complexing acid such as citric or maleic acid in combination with a quaternary ammonium compound or amines such as primary tallow and primary coco amine. The function of the acid, as stated in the patents, is to prevent yellowing of fabrics due to build-up of cationic softener and to provide a complexing site for metal ions contained in soils. U.S. Patent Nos. 4,828,722 to Steltenkamp and U.S. 4,869,836 to Harmalker disclose multicarboxylic acid complexes of tertiary amines formed from a tertiary amine and a carboxylic acid selected from among citric acid and di and tri carboxylic acids having 21 to 54 carbon atoms. In U.S. Patent 4,832,856 is disclosed a fabric softener composition comprising a combination of carboxylic acid and amines having a long chain alkyl or alkenyl radical.
European Patent Publication No. 123,400 to Kardouch discloses detergent compositions containing salts of specified tertiary amines and carboxylic acids which are utilized in the form of modules that pass virtually unchanged through the wash and rinse and then condition the fabric when heated in a dryer. European Patent Publication No. 417,987 describes fabric softening compositions comprised of tertiary amines and carboxylic acids.
Although satisfactory results may be obtained with one or more of these prior art fabric softening compositions, further improvements are needed in terms of being able to provide efficacious fabric softening with a biodegradable cationic fabric softening compound, concomitant with the ability to substantially solubilize and remove mineral encrustation from the fabrics to be treated. This is a particularly important need for European fabric conditioning compositions where the cumulative deposition of mineral salts on fabrics during repetitive laundering in hard water is an acute problem. Moreover, the increased emphasis in Europe on using biodegradable softening compounds which have no toxic effect on aquatic organisms in aqueous effluent streams makes it imperative that conventional softening compounds, most notably, the di-long chain, di-short chain quaternary ammonium compounds be replaced as the softening compounds of choice in commercial rinse-cycle softening compositions with softening compounds which are significantly more compatible with environmental concerns.
SUMMARY OF THE INVENTION The present invention provides environmentally compatible and biodegradable rinse cycle fabric conditioning compositions capable of providing improved softening with significant reduction and solubilization of unwanted mineral encrustations on fabrics to be softened, such encrustations having been generally deposited on the fabrics during the course of prior laundering in water having a high mineral content, which comprises a fabric conditioning mixture of:
(a) at least one of (i) an alkanolamine diester having the general formula:
O
(I (CH2)n-OCR2
HO(CH2)p— N
I II
(CH2)rrr-OCR 1
and;
(ii) an alkanolamine triester having the general formula:
O II
(CH2)n- OCR2
0 I
R3CO — (CH2)p- N . O
' H
(CH,) — OCR1 Wherein R1f R2 and R3 are each independently hydrogenated tallow or soft tallow; and n, m and p are integers from 1 to 4; and (b) unreacted organic acid or mineral acid.
In a preferred embodiment of the invention, the fabric softening composition further contains from about 0.2 to about 5%, by weight, preferably from about 0.5 to about 3%, and most preferably from about 0.5 to 1%, by weight, of a fatty alcohol having from about 10 to about 24 carbon atoms.
In preferred embodiments of the invention, the integers n, m and p in the general formula are 2, and R1 t R2 and R3 are hydrogenated tallow to provide a triethanolamine diester and/or triester.
The invention also encompasses a method for softening fabrics and removing unwanted mineral encrustations therefrom comprising rinsing the fabrics to be treated in an aqueous bath containing an effective amount of a composition comprised of the above-defined fabric conditioning mixture. The present invention is predicated on the discovery that the combination of alkanol amine diester and/or triester fabric softener as defined above with an organic or mineral acid provides a biodegradable softener which has the capability of removing mineral encrustations such as calcium and magnesium salts, and in particular, phosphates and carbonates of calcium and magnesium, which cumulatively deposit on the fabrics during the course of prior laundering in hard water, i.e. water having a mineral content above about 300 ppm, conditions generally associated with European laundering conditions.
A particularly preferred softening compound as described herein comprises a mixture of triethanolamine diester and triester sold by Hoechst Company under the trade designation of E 91/526 acid E 91/516.
DETAILED DESCRIPTION OF THE INVENTION The compositions of the present invention are environmentally compatible and biodegradable rinse cycle fabric conditioning compositions which contain as the active fabric softening compound an alkanolamine diester and/or triester as defined above. The use of such fabric softening compound avoids the more traditional di-long chain, di-short chain quaternary ammonium softeners which are used extensively in commercial rinse cycle softeners, but which presently have become the focus of increasing legislative concerns, particularly in Europe, because of their lack of biodegradability in aqueous effluent streams. The total amount of diester and triester amine in the total composition is from about 1 to 20%, by weight, preferably from about 2 to 10%, by weight.
The second essential ingredient of the fabric conditioning composition is the acid which has a dual function, depending on the acid concentration. The first function is preventive in nature and occurs when the acid in the diluted rinse cycle solution is present in sufficient amount to react with the insoluble salts of the water hardness ions (calcium and magnesium) to form soluble acid salts and to remove any mineral salts which may have deposited on fabrics during the washing step of the wash cycle. The second function is more curative in nature and refers to the removal of mineral encrustations which have been cumulatively deposited during prior washing throughout the fabric's life.
To effect the aforementioned preventive function, an acid concentration of from about 1 to about 8%, by weight, preferably from about 5 to about 8%, is required in the fabric softening composition depending on the dosage used and the hardness of the water. For European washing machines containing about 20 to 25 liters of water, for example, a dosage of 110 to 150 ml of softening composition is typical for use in the rinse cycle; the water hardness varies from about 200 to 400 ppm, most typically about 300 ppm. To effect the curative function of the acid for removal of previously deposited mineral encrustations, an acid concentration of from about 5 to about 25%, by weight, preferably from about 8 to 25%, by weight, is required in the fabric softening composition.
The acid used may be an organic or mineral acid. The organic acids are preferably saturated or unsaturated C2-Cβ carboxylic acids such as citric acid, formic acid, maleic acid, tartaric acid and succinic acid. Citric acid, malonic acid and maleic acid are particularly preferred. A mineral acid, such as HCI, which is particularly effective to protonate the diester amine softening compound, may be advantageously combined with such organic acid, the amount of acid used in excess of protonation being referred to herein as "unreacted". Generally, the concentration of unreacted mineral acid should not exceed about 5%, preferably not more than 2%, by weight, of the fabric conditioning composition so as to prevent unwanted product separation. A carboxylic acid may then be used to supplement the mineral acid up to a total acid content of about 25% without adversely affecting product stability.
An optional fabric conditioning ingredient is a fatty alcohol wherein the hydrophobic group may be a straight or branched chain alkyl or alkenyl group having from about 10 to 24, preferably from about 10 to 20, especially preferably from about 12 to 20 carbon atoms. Specific examples of the fatty alcohol include decanol, dodecanol, tetradecanol, pentadecanol, hexadecanol, octadecanol, lauryl alcohol, palmityl alcohol, stearyl alcohol, oleyl alcohol, and mixtures thereof. Furthermore, the fatty alcohol may be of natural or synthetic origin and my include, for example, mixed alcohol, such as Cι6-C18 alcohols prepared by Ziegler polymerization of ethylene.
The fatty alcohol may be present in the composition in a minor amount relative to the cationic fabric softener such that the ratio, by weight, of the cationic fabric softener to fatty alcohol is in the range of from about 6:1 to 2:1 , preferably about 5:1 to 3:1, and most preferably about 4:1.

Claims

An environmentally compatible and biodegradable fabric conditioning composition capable of providing improved softening with significant reduction and solubilization of unwanted mineral encrustations on fabrics to be softened, such encrustations having been generally deposited on the fabrics during the course of prior laundering in water having a high mineral content, which comprises a fabric conditioning mixture of: (a) at least one of (i) an alkanolamine diester having the general formula:
O
II
Figure imgf000008_0001
and;
(ii) an alkanolamine triester having the general formula:
O II (CH2)n- OCR2 O |
II '
R3CO— (CH2)p- N
1 I J °l (CH2)m— OCRT
Wherein R1f R2 and R3 are each independently hydrogenated tallow or soft tallow; and n, m and p are integers from 1 to 4; and (b) unreacted organic acid or mineral acid.
2. A fabric conditioning composition according to claim 1 wherein in the general formula R1 f R2 and R3 are each hydrogenated tallow, and n, m and p are 2.
3. A fabric conditioning composition according to claim 1 wherein the acid is citric acid.
4. A fabric conditioning composition according to claim 1 wherein the acid is malonic or maleic acid.
5. A fabric conditioning composition according to claim 1 which contains from about 1 to 20%, by weight, of said alkanolamine diester and triester and from about 1 to 25%, by weight, of said acid.
6. A fabric conditioning composition according to claim 1 which further includes from about 0.2 to about 5%, by weight, of a fatty alcohol having from about 10 to about 24 carton atoms.
7. A fabric conditioning composition according to claim 6 wherein the fatty alcohol is a C ι β-C ι Q alcohol.
8. A method for softening fabrics and removing unwanted mineral encrustation therefrom comprising rinsing the fabrics to be treated in an aqueous bath containing an effective amount of a rinse cycle fabric conditioning composition comprising a fabric conditioning mixture of: (a) at least one of (i) an alkanolamine diester having the general formula:
O II
(CH2)n-OCR2 1
HO(CH2)p— N
I I ° II
(CH2)rn-OCR1
and;
(ii) an alkanolamine triester having the general formula:
Figure imgf000009_0001
Wherein R.,, R2 and R3 are each independently hydrogenated tallow or soft tallow; and n, m and p are integers from 1 to 4; and (b) unreacted organic acid or mineral acid.
9. The method of claim 8 wherein the fabric conditioning composition comprises from about 1 to 20%, by weight, of said alkanolamine diester and triester and from about 1 to 25%, by weight, of said acid.
10. The method of claim 8 wherein the acid is citric acid.
11. The method of claim 8 wherein the acid is malonic or maleic acid.
12. The method of claim 8 wherein the fabric conditioning composition comprises from about 1 to 20%, by weight, of said diester amine and from about 1 to 25%, by weight, of said acid.
13. The method of claim 8 wherein the fabric conditioning composition further includes from about 0.2 to about 5%, by weight, of a C16-C18 alcohol.
PCT/US1993/007608 1992-08-21 1993-08-17 Fabric conditioning composition WO1994004641A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP93920019A EP0656934A1 (en) 1992-08-21 1993-08-17 Fabric conditioning composition

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US07/934,097 1992-08-21
US07/934,097 US5288847A (en) 1992-08-21 1992-08-21 Fabric conditioning composition containing alkanol amine ester and acid
US8722393A 1993-07-02 1993-07-02
US08/087,223 1993-07-02

Publications (1)

Publication Number Publication Date
WO1994004641A1 true WO1994004641A1 (en) 1994-03-03

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Family Applications (1)

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Country Status (2)

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WO (1) WO1994004641A1 (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997042279A1 (en) * 1996-05-03 1997-11-13 Akzo Nobel N.V. High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine
WO2000006678A1 (en) * 1998-07-30 2000-02-10 The Dow Chemical Company Composition useful for softening, cleaning, and personal care applications
EP1096055A1 (en) * 1998-06-11 2001-05-02 Kao Corporation Softener composition
WO2001032813A1 (en) * 1999-11-01 2001-05-10 Kao Corporation Quaternary ammonium salt composition
EP1840197A1 (en) * 2006-03-31 2007-10-03 Kao Corporation, S.A. Composition for rinsing and drying vehicles

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2525771A (en) * 1947-05-12 1950-10-17 Arkansas Company Inc Fatty acid-aliphatic amine polyglycol combinations useful as textile assistants and process of producing the same
EP0507973A1 (en) * 1991-04-10 1992-10-14 FRATELLI LAMBERTI S.p.A. Biodegradable compositions for use as textile softeners
WO1992018684A1 (en) * 1991-04-12 1992-10-29 Henkel Kommanditgesellschaft Auf Aktien Use of esters as a textile softening agent

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2525771A (en) * 1947-05-12 1950-10-17 Arkansas Company Inc Fatty acid-aliphatic amine polyglycol combinations useful as textile assistants and process of producing the same
EP0507973A1 (en) * 1991-04-10 1992-10-14 FRATELLI LAMBERTI S.p.A. Biodegradable compositions for use as textile softeners
WO1992018684A1 (en) * 1991-04-12 1992-10-29 Henkel Kommanditgesellschaft Auf Aktien Use of esters as a textile softening agent

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Derwent's abstract, No 85-151 426/25, week 8525, ABSTRACT OF SU 112 6-5 971, (AS LATV WOOD CHEM), 1983-02-04 *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997042279A1 (en) * 1996-05-03 1997-11-13 Akzo Nobel N.V. High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine
CN1097090C (en) * 1996-05-03 2002-12-25 阿克佐诺贝尔公司 Preparation of high Di (alkyl fatty ester) quaternary ammonium salt compound from triethanolamine
EP1096055A1 (en) * 1998-06-11 2001-05-02 Kao Corporation Softener composition
EP1096055A4 (en) * 1998-06-11 2002-06-26 Kao Corp Softener composition
US6521588B1 (en) 1998-06-11 2003-02-18 Kao Corporation Softener composition
WO2000006678A1 (en) * 1998-07-30 2000-02-10 The Dow Chemical Company Composition useful for softening, cleaning, and personal care applications
WO2001032813A1 (en) * 1999-11-01 2001-05-10 Kao Corporation Quaternary ammonium salt composition
US7214718B1 (en) 1999-11-01 2007-05-08 Kao Corporation Quaternary ammonium salt composition
EP1840197A1 (en) * 2006-03-31 2007-10-03 Kao Corporation, S.A. Composition for rinsing and drying vehicles
ES2294923A1 (en) * 2006-03-31 2008-04-01 Kao Corporation, S.A. Composition for rinsing and drying vehicles

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