CA1232709A - Aqueous concentrated fabric softening composition - Google Patents

Aqueous concentrated fabric softening composition

Info

Publication number
CA1232709A
CA1232709A CA000479166A CA479166A CA1232709A CA 1232709 A CA1232709 A CA 1232709A CA 000479166 A CA000479166 A CA 000479166A CA 479166 A CA479166 A CA 479166A CA 1232709 A CA1232709 A CA 1232709A
Authority
CA
Canada
Prior art keywords
fatty
weight
fabric softening
softening composition
aqueous concentrated
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
Application number
CA000479166A
Other languages
French (fr)
Inventor
Robert M. Butterworth
John R. Martin
Edwin Willis
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Unilever PLC
Original Assignee
Unilever PLC
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
Application filed by Unilever PLC filed Critical Unilever PLC
Application granted granted Critical
Publication of CA1232709A publication Critical patent/CA1232709A/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/835Mixtures of non-ionic with cationic compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005Other compounding ingredients characterised by their effect
    • C11D3/001Softening compositions
    • C11D3/0015Softening compositions liquid
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/52Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/523Carboxylic alkylolamides, or dialkylolamides, or hydroxycarboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain one hydroxy group per alkyl group
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/52Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/526Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 are polyalkoxylated
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/62Quaternary ammonium compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/72Ethers of polyoxyalkylene glycols
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/74Carboxylates or sulfonates esters of polyoxyalkylene glycols

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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)
  • Chemical Or Physical Treatment Of Fibers (AREA)

Abstract

A B S T R A C T

An aqueous concentrated fabric softening composition comprises an aqueous base, more than 10% of a water-insoluble cationic fabric softener and at least 4%
of a nonionic material which includes an alkylene oxide adduct of a fatty alcohol, acid, ester or amide with not more than 7 alkylene oxide groups per molecule. The total level of cationic and nonionic components is preferably less than 25%. The nonionic component improves processing by lowering the initial viscosity of the product.

Description

1~327~9 - l - C.3034 AQUEOUS CONCENTRATED FABRIC SOFTENING COMPOSITION

This invention relates to an aqueous concentrated fabric softening composition, in particular to such a composition which contains more than 10% by weight of a water-insoluble cat ionic fabric softener.

Concentrated fabric softening compositions containing more than 10% by weight of a water-insoluble cat ionic fabric softener suffer from the disadvantage of high viscosities which inter aria makes such products difficult to process. It has been proposed in European Patent Specification No EP-A-56695 (PROCTER & GAMBLE) that viscosity can be controlled by the use of small quantities, specifically up to 3% by weight of alkoxylated amine.

We have now surprisingly discovered that the processing of concentrated fabric softening compositions can be improved by the inclusion of higher levels of other specific alkoxylated fatty compounds. The benefit of this improved processing can be seen in a lower initial product viscosity.

~X;~27~3~
- 2 - C.3034 Thus, according to the invention, there is provided an aqueous concentrated fabric softening composition comprising:

( i) an aqueous base;

( ii) more than 10% by weight of a water-insoluble cat ionic fabric softener; and (iii) more than 4% by weight of a non ionic material which comprises an alkaline oxide adduce of a fatty compound selected from fatty alcohols, fatty acids, fatty esters, and fatty acid asides, the fatty compound containing at least 10 carbon atoms and the adduce containing an average of not more than 7 alkaline oxide groups per molecule, when the fatty compound is a fatty acid or a fatty ester and not more than 4 alkaline oxide groups per molecule when the fatty compound is a fatty alcohol or a fatty acid aside, the total level of the cat ionic softener and the non ionic material being not more than 36% by weight, preferably not more than about 25% by weight. 5 The level of cat ionic softener in the composition is preferably from 10.5% to 21% by weight. The level of the non ionic material in the composition is preferably from 4.5% to 12.0% by weight. The weight ratio of the 0 cat ionic softener to the non ionic material is preferably at least 1:1, such as between about 1.5:1 and about 3:1.

The water-insolub~e cat ionic fabric softener can be any fabric-substantive cat ionic compound which has a US volubility in water at pi 2.5 and 20C of less than 10 g/l. Highly preferred materials are qua ternary ammonium ~3270~
_ 3 _ C.3034 salts having two C12-C24 alkyd or alkenyl chains, optionally substituted or interrupted by functional groups such as -OH, -O-, -CON, -COO-, etc.

Well known species of substantially water-insoluble qua ternary ammonium compounds have the formula \ / 3 N X

wherein Al and R2 represent hydrocarbyl groups from about 15 12 to about 24 carbon atoms; R3 and R4 represent hydrocarbyl groups containing from 1 to about 4 carbon atoms; and X is an anion, preferably selected from halide, methyl sulfate and ethyl sulfate radicals. Representative examples of these qua ternary softeners include disallow dim ethyl ammonium chloride; disallow dim ethyl ammonium methyl sulfate; dihexadecyl dim ethyl ammonium chloride;
di(hydrogenated tallow alkyd) dim ethyl ammonium chloride;
dioctadecyl dim ethyl ammonium chloride; dieicosyl dim ethyl ammonium chloride; didocosyl dim ethyl ammonium chloride;
di(hydrogenated tallow) dim ethyl ammonium methyl sulfate;
dihexadecyl deathly ammonium chloride; diIcoconut alkyd) dim ethyl ammonium chloride. Disallow dim ethyl ammonium chloride, di(hydrogenated tallow alkyd) dim ethyl ammonium chloride, di(coconut alkyd) dim ethyl ammonium chloride and di(coconut alkyd) dim ethyl ammonium methosulfate are preferred.

Another class of preferred water-insoluble cat ionic materials are the alkylimidazolinium salts believed to have the formula:

1~3~ 4 - C.3034 I
wherein R6 is an alkyd or hydroxyalkyl group containing from 1 to 4, preferably 1 or 2 carbon atoms, R7 is an alkyd or alkenyl group containing from 8 to 25 carbon atoms, R8 is an alkyd or alkenyl group containing from to 25 carbon atoms, and Rug is hydrogen or an alkyd containing from 1 to 4 carbon atoms and A is an anion, preferably a halide, methosulfate or ethosulfate.
Preferred imidazolinium salts include l-methyl-l-(tallowylamido-) ethyl -2-tallowyl- dodder imidazolinium methosulfate and l-methyl-l-(palmitoylamido)ethyl -2~octadecyl-4,5- dodder-imidazolinium chloride. Other useful imidazolinium materials are 2-heptadecyl-1-methyl-1- (2-stearylamido)-ethyl-imidazolinium chloride and 2-lauryl-1-hydroxyethyl-25 _ l-oleyl-imidazolinium chloride.

Representative commercially available materials of the above classes are the qua ternary ammonium compounds Argued 2HT (ox AWAKES); Noramium MUSH Rex SEIKO); Aliquat-2HT
(Trade Mark of General Mills Inch and the imidazolinium compounds Varisoft 475 (Trade Mark of Shrieks Company, Columbus Ohio) and Rocket Wow (Trade Mark of REDO).

~X327~9 _ 5 _ C.3034 The non ionic material is, or includes, an alkaline oxide adduce of various fatty compounds as specified above, but may also include other alkoxylated or non-alkoxylated non ionic materials.

Alkaline oxide adduces of fatty alcohols useful in the present invention, preferably have the general formula:

(On Noah wherein R10 is an alkyd or alkenyl group having at least 10 carbon atoms, most preferably from 10 to 22 carbon atoms, y is not more than 4.0, such as from about 0.5 to about 3.5 and n is 2 or 3. Examples of such materials include Synperonic A (ox ICY) which is a C13-C15 alcohol J` with about three ethylene oxide groups per molecule and Empilan By (ox Martian) which is Laurie alcohol LEO.
Alkaline oxide adduces of primary alcohols are preferred over those of secondary alcohols.

Alkaline oxide adduces of fatty acids useful in the present invention, preferably have the general formula R -I (CnH2n)yH

wherein R10, and n are as given above and y is preferably not more than 4.0, such as from about 0.5 to about 3.5.
Suitable examples include ESONAL:~0334 (ox Diamond Shamrock) which is a tallow fatty acid with about 2.4 ethylene oxide groups per molecule.

Alkaline oxide adduces of fatty esters useful in the present invention include adduces of moo-, dip or trimesters of polyhydric alcohols containing 1 to 4 carbon ~e,qof~ 5 ye US

Lo 6 - C.3034 atoms with not more than 4.0, such as from about OHS to about 3.5 alkaline oxide groups per molecule; such as coconut or tallow oil (triglyceride) LEO (ox Sterno Dobbs).

Alkaline oxide adduces of fatty acid asides useful in the present invention, preferably have the general formula jCnH2nO) XTI

Rho -I -N
\
(Cn~2n) z wherein R10 and n are as given above, and x and z in total are not more than 4.0, such as from about 0.5 to about
3.5, while one of x and z can be zero. Examples of such materials include tallow monoethanolamide and diethanolamide, and the corresponding coconut and soya compounds.

The viscosity of the product, when measured at 110 sea l shear rate should be less than about 150 cup, 25 preferably between about 20 and about 100 cup and the product can ye added as such to a fabric rinse liquor or may be pre-diluted with water.

Preferably, the compositions of the invention contain substantially no anionic material, in particular no anionic surface active materials. If such materials are present, the weight ratio of the cat ionic material to the anionic material should preferably be more than 10:1, such as more than 100:1.
The compositions may include electrolytes to assist in controlling the viscosity of the product. A suitable ~Z3~:7~
_ 7 C.3034 electrolyte level in the compositions is from about 0.01%
to about 0.5%, most preferably from about 0.02% to about 0.2%, measured as the an hydrous salt. Examples of suitable materials include the ionic salts of sodium, potassium, lithium, magnesium, calcium or aluminum, such as lithium chloride, sodium chloride, ammonium chloride, sodium methosulphate, sodium bonniest, calcium chloride, magnesium chloride or aluminum chloride. Of these, sodium and potassium salts are less preferred.

The compositions may include low levels of solvents for the cat ionic fabric softener. Indeed, the cat ionic raw materials will often include isopropanol as a solvent It is preferred that the level of isopropanol or any other C1-C4 mandrake alcohol in the composition is less than about 10% by weight, most preferably less than about 5% by weight.

Additionally the composition can contain substances for maintaining the stability of the product on cold storage. examples of such substances include polyhydric alcohols such as ethylene glycol, propylene glycol, glycerol and polyethylene glycol. A suitable level for such materials is from about 0.5% to about 5%, preferably about 1.0% to 2.0% by weight.

The compositions of the invention may further include other additional ingredients including colorants, perfumes, preservations, anti-foams, optical brighteners, pacifiers, pi buffers (the preferred pi for the compositions is between about 3 and about 8, such as from about 4 to about 6), further viscosity modifiers, non-cationic fabric conditioning agents, anti-shrinkage agents, anti-wrirkle agents, fabric crisping agents, spotting agents, soil-release agents, germicides, anti-oxidants and anti-corrosion agents.

>7~g - 8 - C.3034 The compositions of the invention may be prepared by a variety of methods. One suitable method is to form a molten mixture of the cat ionic fabric softener and the non ionic material, add this molten mixture to water with stirring to form a dispersion and thereafter adding any optional ingredients.

The invention will now be illustrated by the following Examples, where all parts and percentages are by weight. Where commercially available materials are referred to, the percentages quoted are of the active ingredients therein. Viscosities were measured in a Hake Rotorviscometer (Model REV 2) at 110 sea 1 at 25C.

Compositions were prepared according to the formulations in the following Tables. The compositions were prepared by forming a molten mixture of the cat ionic and non ionic ingredients at 65C, adding to water at the same temperature, stirring to form a dispersion, adding electrolyte in the form of a saturated solution, cooling and then adding perfume. The compositions were made in batches of 100g. Stirring was continued for 7 minutes at zoo rum.

I

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r l us I I I I O rut I
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Jo pa) rut 11~ 0 _ ago rut I US: O r3 . a) o o rt3_ O Et I i 4 a æ I: I pa owe . ,, rut r;3 I N 'O 3 a r3 I) I) a) 1~3 rut 'C3 3 3 3 Q4 0 (I I o at O O rlS-l I g rho pa rut rut I.) O
I t,) I rut r-l rut X I 0 O (I I
l H O En O 3 u-~L~3;27~9 - I - C.3034 In order to demonstrate the effect of the degree of alkoxylation of the non ionic adduce on the initial viscosities of products according to the invention, the following compositions were prepared using the method described in Example 1:

Example No: 19 AYE 20 AYE
10 Ingredients (%) Argued 2HT 10.5 10.5 10.5 10.5 Synperonic Aye 7.0 - - -Synperonic Aye - 7.0 15 Cocodiethanol aside - - 7.0 Genogen CA 0505 - - - 7.0 Calcium chloride 0.05 0.05 0.05 Water -----------balance-----------Initial viscosity (cup) 40 500 78 >500 Notes:

3 - A commercially available alkoxylated alcohol which is approximately straight chain I -C15 alcohol with 3 HO groups per molecule.
4 - As Synperonic A but with 11 HO groups per molecule.
5 - A commercially available material (ox HOECHST) believed to be the addition product of coconut fatty monoethanolamide with 5 moles of ethylene oxide.

Claims (6)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. An aqueous concentrated fabric softening composition comprising:

( i) an aqueous base;

( ii) more than 10% by weight of a water-insoluble cationic fabric softener; and (iii) more than 4% by weight of a nonionic material which comprises an alkylene oxide adduct of a fatty compound selected from fatty alcohols, fatty acids, fatty esters, and fatty acid amides, the fatty compound containing at least 10 carbon atoms and the adduct containing an average of not more than 7 alkylene oxide groups per molecule, when the fatty compound is a fatty acid or a fatty ester and not more than 4 alkylene oxide groups per molecule when the fatty compound is a fatty alcohol or a fatty acid amide, the total level of the cationic softener and the nonionic material being not more than 36% by weight.
2. An aqueous concentrated fabric softening composition according to Claim l, wherein the level of said water-insoluble cationic fabric softener is from 10.5% to 21% by weight of the composition.
3. An aqueous concentrated fabric softening composition according to Claim 1, wherein the level of said nonionic material is from 4.5% to 12% by weight of the composition.
4. An aqueous concentrated fabric softening composition according to Claim 1, wherein the weight ratio of said water-insoluble cationic fabric softener to said nonionic material is at least 1:1.
5. An aqueous concentrated fabric softening composition according to Claim 1 further comprising an electrolyte selected from the ionic salts of lithium, magnesium, calcium, aluminum and mixtures thereof.
6. A process for preparing an aqueous concentrated fabric softening composition according to Claim 1, wherein a molten mixture of the cationic softener and the nonionic material is added to water with stirring to form a dispersion.
CA000479166A 1984-04-19 1985-04-15 Aqueous concentrated fabric softening composition Expired CA1232709A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB848410322A GB8410322D0 (en) 1984-04-19 1984-04-19 Aqueous concentrated fabric softening composition
GB8410322 1984-04-19

Publications (1)

Publication Number Publication Date
CA1232709A true CA1232709A (en) 1988-02-16

Family

ID=10559922

Family Applications (1)

Application Number Title Priority Date Filing Date
CA000479166A Expired CA1232709A (en) 1984-04-19 1985-04-15 Aqueous concentrated fabric softening composition

Country Status (6)

Country Link
EP (1) EP0159919A3 (en)
JP (1) JPS60231866A (en)
AU (1) AU561378B2 (en)
CA (1) CA1232709A (en)
ES (1) ES8706196A1 (en)
GB (2) GB8410322D0 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4676915A (en) * 1985-03-27 1987-06-30 Colgate-Palmolive Company Antistatic composition and detergent compositions containing antistatic components
GB8619153D0 (en) * 1986-08-06 1986-09-17 Unilever Plc Fabric conditioning composition
ATE82770T1 (en) * 1987-09-23 1992-12-15 Procter & Gamble LINEAR ALKOXYLATED ALCOHOL-CONTAINING STABLE, BIODEGRADABLE LAUNDRY SOFTENER COMPOSITIONS.
DE4301459A1 (en) * 1993-01-20 1994-07-21 Huels Chemische Werke Ag Aqueous fabric softener for the treatment of textiles
EP1445303A3 (en) * 1994-10-14 2004-10-20 Kao Corporation Liquid softener composition
US6191101B1 (en) * 2000-05-26 2001-02-20 Colgate-Palmolive Co. Fabric softening compositions providing enhanced performance and containing cationic softeners and fatty amides
WO2023170120A1 (en) * 2022-03-10 2023-09-14 Unilever Ip Holdings B.V. Concentrated fabric conditioner

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3974076A (en) * 1974-01-11 1976-08-10 The Procter & Gamble Company Fabric softener
US4140641A (en) * 1978-03-17 1979-02-20 Colgate-Palmolive Company Concentrated liquid detergent with fabric softener
FR2482636A1 (en) * 1980-05-14 1981-11-20 Lesieur Cotelle Et Associes Sa CONCENTRATED SOFTENING COMPOSITION FOR TEXTILE FIBERS
DE3025369A1 (en) * 1980-07-04 1982-01-28 Hoechst Ag, 6000 Frankfurt SOFT SOFT CONDENSER CONCENTRATE
DD154712A1 (en) * 1980-07-10 1982-04-14 Rainer Blum WAESCHENACHBEHANDLUNGSMITTEL
DE3263800D1 (en) * 1981-01-16 1985-07-04 Procter & Gamble Textile treatment compositions
ATE20534T1 (en) * 1981-03-07 1986-07-15 Procter & Gamble TEXTILE TREATMENT AGENTS AND THEIR PREPARATION.
US4439335A (en) * 1981-11-17 1984-03-27 The Procter & Gamble Company Concentrated fabric softening compositions
DE3150178A1 (en) * 1981-12-18 1983-06-30 Hoechst Ag, 6230 Frankfurt "CONCENTRATED SOFT SOFT DETERGENT"
DE3150179A1 (en) * 1981-12-18 1983-06-23 Hoechst Ag, 6230 Frankfurt CONCENTRATED PRE-MIXTURES OF SOFT SOFTENER
DE3218667A1 (en) * 1982-05-18 1983-11-24 Hoechst Ag, 6230 Frankfurt CONCENTRATED SOFT SOFTENER
ZA834209B (en) * 1982-06-22 1985-01-30 Colgate Palmolive Co Concentrated fabric softening compositions and method for making same
FR2540901B1 (en) * 1983-02-14 1986-08-29 Elf Aquitaine CONCENTRATED COMPOSITIONS OF TEXTILE SOFTENERS
DE3373492D1 (en) * 1983-06-10 1987-10-15 Camp Jabones Stable concentrated aqueous dispersions of water-insoluble cationic compounds and preparation thereof

Also Published As

Publication number Publication date
ES542356A0 (en) 1987-06-01
JPS60231866A (en) 1985-11-18
GB2157730A (en) 1985-10-30
AU4124885A (en) 1985-10-24
GB8509804D0 (en) 1985-05-22
AU561378B2 (en) 1987-05-07
EP0159919A3 (en) 1987-03-18
GB2157730B (en) 1988-04-13
ES8706196A1 (en) 1987-06-01
EP0159919A2 (en) 1985-10-30
GB8410322D0 (en) 1984-05-31

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