CA1323278C - Free flowing anionic detergent and a method of production thereof - Google Patents

Free flowing anionic detergent and a method of production thereof

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Publication number
CA1323278C
CA1323278C CA000607122A CA607122A CA1323278C CA 1323278 C CA1323278 C CA 1323278C CA 000607122 A CA000607122 A CA 000607122A CA 607122 A CA607122 A CA 607122A CA 1323278 C CA1323278 C CA 1323278C
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Prior art keywords
free flowing
powdered
high active
anionic
detergent composition
Prior art date
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Expired - Fee Related
Application number
CA000607122A
Other languages
French (fr)
Inventor
John Maden
Lycourgos Loudiadis
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Cussons International Ltd
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Cussons International Ltd
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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
    • C11D11/00Special methods for preparing compositions containing mixtures of detergents
    • C11D11/04Special methods for preparing compositions containing mixtures of detergents by chemical means, e.g. by sulfonating in the presence of other compounding ingredients followed by neutralising
    • 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
    • C11D11/00Special methods for preparing compositions containing mixtures of detergents
    • 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
    • C11D17/00Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0034Fixed on a solid conventional detergent ingredient

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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)
  • Sorption Type Refrigeration Machines (AREA)
  • Control Of Motors That Do Not Use Commutators (AREA)

Abstract

ABSTRACT A FREE FLOWING ANIONIC DETERGENT AND METHOD OF PRODUCTION THEREOF A method of producing a free flowing, high active, particulate anionic detergent comprising the step of adsorbing an anionic surfactant acid onto a powdered or granular material such as a phosphate, carbonate, bicarbonate or silicate so as to form an agglomerate. No water is added during the agglomeration stage. The agglomerate may subsequently be coated with a silicate and/or an alkaline salt preferably in a fluidised bed.

Description

3 ~

A FREE FLOWING ANIONIC DETE~GENT AND METHOD
OF PRODUCTION THEREOF

This invention relates to detergents, and more particularly, to free flowing, high active anionic detergents.
High active detergents, for the purposes of the present invention, may be defined as detergents comprising more than 1 29d active matter .
Free flowing, for the purposes of the present invention, may be defined as sufficiently mobile as to be capable of being poured or dispensed reproducably as a measured quantity.
It is desirable that detergent powders exemplify certain characteristics, namely, the detergent powder should be non-dusty, free flowing, easily handled, easily dissolved and stable under normal storage conditions.
A large proportion of the worldwide detergent market uses high foaming powder surfactants, most of which are based on anionic active lS matter ingredients.
It has hitherto been common practice to produce detergents in powder form by making up a slurry of the various ingredients in water and subsequently spray drying the slurry to yield a powder- of typical bulk density 0 . 2 to 0 . 5 gms/ml . This method of manufacture is expensive because heat is required to evaporate the water which was ini~ialiy added and yet is not required in the final product.
A further method of manufacture of detergents in powder form is by so called 'dry neutralisation'. Dry neutralisation and associated agglomeration is normally regarded as a three part process:
1. Dry adsorption of an alkyl aryl sulphonic acid onto the surface of an alkaline base.

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2. Addition of water to affect the reaction of the alkali and sulphonic acid to form an alkaline sulphonate which binds the constituents to produce a neutralised de-tergent agglomerate and 3. Coating the outside of the agglomerate with a layer of dessicant material such as sodium tripolyphosphate, sodium carbonate or silicate.
It has previously been assumed that: there is a reasonably well described limitation on the amount of alkyl aryl sulphonic acid which can be adsorpted onto the surface of various alkaline bases without first causing over agglomeration or poor flow properties. For example it has been claimed that the adsorptive characteristics of tripolyphosphate or other adsorptive materials are a function of their surface area. Therefore, sodium tripolyphosphate (STPP) in powder form must have greater adsorptivity than in granular form. Definitive tables of the adsorptivity of STPP and other alkalies have been published in the past giving the adsorptivity of various powders with regard to the uptake of alkyl aryl sulphonic acid, for example do decyl benzene sulphonic acid (DDBSA . ) This, theoretically, limits the amount of active matter which can be formulated into a detergent powder produced by dry neutralisation.
The table (A) below shows commonly accepted limitations of the adsorptlvity of various bases.
TABLE A
g DDBSA/1 OOg alkali salt STPP Powder 32 . 5 STPP low density granular 2 . 0 STPP regular density granular 2 . l soda ash ( powder ) 2 . 2 , : .. ,.. : .

: -:~ .

lc~23278 soda ash (granular) 0.2 Sodium metasilicate anhydrous 0.1 Sodium metasilicate 5H20 0.1 It has previously been assumed that the addition of approximately 5 1-2 % of water was necessary to cause in situ neutralisation of sulphonic acids with alkaline bases. The product was not thought to be stable until this reaction had been completed. It has previously been assumed that a dessicant should be used to coat the outside of the agglomerate to adsorb free water, usually by hydration of the dessicant, to obtain lO a free flowing product.
According to a first aspect of the present invention, there is provided a method of producing a free flowing, high active, anionic detergent comprising the step of adsorbing an anionic surfactant acid onto a powdered or granular material to l`orm an agglomerate without 15 the addition of water in the agglomeration stage.
It has been discovered that the powdered or granular detergent composition derived from this method suprisingly has a subs-tantially uniform particle size and may comprise high levels of surfactant acid successfully exceeding the maximum surfactant acid content of the 2 0 pr ior art .
According to a second aspect of the present inven-tion there is provided a free flowing, high active, anionic powdered or granular detergent composition comprising an anionic surfactant acid adsorped onto a powdered or granular material, said detergent composition having 25 a particle size distribution substantially within the range from 248 microns to 1752 microns.
According to a third aspect of the present invention there is .. . . , . . ~
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provided a free flowing, high active, anionic, powdered or granular detergent composition comprising a surfactant acid adsorped onto a powdered or granular material the surfactant acid being present in the range from 12 to 40% by weight of the total composition and the powdered 5 or granular material being present within the range from 20 to 50% by weight of the total composition.
In a preferred embodiment of the invention, the anionic surfactant acid is adsorbed onto heated, dry, powdered, or granular material.
In a preferred embodiment of the invention the anionic surfactant acid lO is adsorbed onto heated dry powdered or granular form preferably in a fluidised bed.
In a further preferred embodiment, the agglomerate so formed is then coated by the application of a silicate and/or alkali, preferably in a fluidised bed. The temperature of the inital part of the fluidised bed 15 is preferably above 50C and more preferably in the range from 85 to Any suitable anionic surfactant acid may be used. Suitable examples of such are as follows: alkyl aryl sulphonic acids, fatty acid sulphonic acids, olefin sulphonic acids, fatty alcohol ether sulphuric acid, fatty 20 methyl ester sulphonic acid, alkane sulphonic acids. More particularly alkyl aryl sulphonic acids containing an alkyl group with 9-20 carbon atoms and a sulphonic acid or sulphuric acid ester group (included in the term alkyl is the alkyl portion of the aryl groups), or fatty acid sulphuric acids obtained by sulphating alcohols with 8-18 carbon atom 25 chains. Especially valuable are linear straight chaln alkyl benzene sulphonic acids in which the average number of carbon atoms in the alkyl group is from 11 to 13. The amoun-t of anionic . . . , :~ .. .. : , ~

:.,-: , .:,.
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~32~ 8 surfactant acid added is preferably in the range 12% to 40%, more preferably from 12% to 35% and even more preferably from 12% to 30% of the final product weight for weight .
We have discovered that we can adsorb up to at least 50gm 5 DDBDA/lOOgm STPP powder when operating under the conditions of the invention thus significantly exceeding the amounts known to have been adsorbed in previously published work, whilst still retaining the free flowing na-ture of the end product.
The powdered or granular material may comprise any suitable alkali, lO or alkalies, alone, or in combination with other additional ingredients.
Examples of suitable alkalies are as follows: Sodium phosphates, for example sodium tripolyphosphate, sodium carbonate, sodium bicarbonate, sodium silicate or other similar alkalies including potassium or magnesium salts. The amount of alkali is preferably in the range 1096 to 95% and 15 more preferably 60% to 95% final product weight for weight.
Additional ingredients may include the following: bleaching agents for example Sodium Perborate, corrosion inhibitors or alkaline additives, for example, Sodium Silicates, inert fillers, for example Sodium Sulphate, surfactants, optical brighteners, preventors of soil redeposition, (for 20 example, sodium carboxy-methyl cellulose, ) dedusting agents and solubilisers, such as sodium xylene sulphonate, enzymes, chelating agents, perfumes, softening agents, defoamers, bleach activators, soap, and non ionic active material.
Any suitable apparatus may be used, but this may have to be 25 adapted to run under the appropriate conditions so as to maintain dry conditions during the agglomeration stage. Examples of such apparatus 13'~f3278 are as follows:
l. Static or moving machines with dividers or blades or paddles to mix the powders. These include twin shell blenders or V blenders, baffled drums and ribbon or paddle blenders.
5 2. Air suspension machines which suspend the particles in air whilst liquid is sprayed onto said particles. The particle size increases until the particles are too heavy to be suspended at which time they fall from the air stream.
3. Apparatus in which air is used to fluidise the particles making lO them act in a similar manner to a liquid, for example, a fluidised bed.
Sample powdered or granular detergents derived from this method exhibit the following characteristics:
Particle Size no more than 3% by weight of the particles are larger than l700 15 microns no more than l % by weigh-t of the particles are less than 250 microns average particle size 1100 to 1300 microns Bulk density: untapped 600-720 gm/ml tapped: 730-830 gm/ml moisture content: less than 4~ W/W
. . _ . . _ .
angle of repose average: 37 to 38C
with minimum 36 maximum 41 sliding angle: minimum 25 maximum 28 flowrate: 30-41 cc/sec through standard orifice.
compressibility: 7-15%
. . . _ _ ;, ',., 13 23S~7~

Composition of anionic detergent granulate:

The detergent composition comprises 5 to 40g~ preferably 10 to 35%
and more preferably 12 to 30% by weight of the final composition of an anionic surfactant acid for example Sodium alkyl ar~yl sul~hate. The 5 detergent composition comprises 20 to 50% preferably 25 to 4S% and more preferably 30 to 40% by weight of the final composition of the powdered or granular material such as the alkaline material sodium tripolyphoshphate. The detergent composition may also comprise any of the optical ingredients listed on page 5 including for example any of lO the following: soda ash, sodium sulphate, sodium carboxy methyl cellulose, optical bleaches, sequestering agents, sodium silicates etc.
For the purpose of the present invention:-the angle of repose is defined as the angle from the horizontal tothe line of slope of a heap of powder, the heap having been formed 15 by directing powder through a funnel into the centre of a circular horizontal surface. The funnel is slowly raised to allow the heap to form immediately beneath it.
The flow rate of the powder is de~ined as the rate in cubic centimetres per second that will flow through a 1 . 25cm diameter orifice 20 with a smooth PVC funnel e~<panding at 10 to the vertical above the or if ice .
The angle of slide is defined as the minimum angle between -the horizontal and an inclined surface when a powder slides by gravity en masse down that surface, the surface being a smooth, wooden unpolished 25 medium. The powder is scattered as a layer no more than 20mm deep on the surface. The surface is raised slowly until the sliding condition is achieved~

- . ;

13232~8 The compressibility of the powder is defined as the percentage of initial volume lost when a sample is subjected to a compressive load, the compressive load being provided by a 10Kg weight which is applied to a cylinder of powder of 69mm diameter for a period of 3 5 minutes.
The invention will now be described further by the following Examples:

The following mixture was prepared by dry blending and then l0 fed at a rate of typically 1.83 kg per minute onto a horizontal fluidised bed. No water was added. The inital part of the fluidised bed was heated to above 80C and retained at this temperature during the experiment .
Material ~6 W/W
15 Sodium Tripolyphosphate 44 . 8 Sodium Carbonate 23.4 Sodium Carboxy-Methyl Cellulose 2.40 Sodium Sulphate 29 . 00 Optical Brightener ~TINOPAL* CBS-X) 0.40 *TINOPAL is a Trade Mark of Ciba-Geigy.
Two liquids, as defined below, were sprayed sequentially along the fluidising bed onto the fluidised powder.
LIQUID 1. Do Decyl Benzene Sulphonic Acid ~DDBSA) at a spray rate of 390g/min.
25 LIQUID 2. A solution comprising % WIW
a) Sodium Silicate ~2:1 Si02:Na20~ 40.00 ~,. - ~ i , , : '~

~32~2'~'~
g b) Pigment blue 15:1 (46% Dispersion 0.18 c ) Tetra sodium sait of ethylene diamine tetra acetic acid 3.66 d ) Water 56 .16 The solution was applied at a spray rate of 390g/min. The combined addition of alkyl aryl sulphonic acid and silicate solution equated to a 30.0% w/w combined percentage liquid additions.
After processing, chemical analysis indicated the powders had the following chemical content.
% W/W
Active Detergent 15 . 6 (calculated as Sodium Alkyl Aryl Sulphonate - Molecular Weight 322) Sodium Tripolyphosphate 32.4 lS (calculated as P205) Moisture 1 . 53 The product was a dust free, free flowing granular agglomerate.

The foliowing powder mixtures were prepared and used as in EXAMPLE
20 1, % WlW
Sodium Tripolyphosphate 57 . 60 Sodium Carbonate 23 . 00 Sodium Carboxy-Methyl Cellulose 2 . 40 25 Sodium Sulphate 16.60 Optical Brightener (TINOPAL* CBS-X) 0.40 *TINOPAL is a Trade Mark of Ciba-Geigy.

.... .. . . .

~32`~278 The composition of the two liquids sprayed along the fluidised bed was as in EXAMPLE 1.
LIQUID 1 was applied at a spray rate of 600g/min.
LIQUID 2 was applied at a spray rate of 390g/min The combined addition of alkyl aryl sulphonic and silicate solultion equated to a combined percentage liquid addition of 35.0% W/W.
After processing, chemical analysis indicated the powder had the following chemical content.
% W.W.
10 Active Detergent 23 . 9 (calculated as Sodium Alkyl Aryl Sulphonate - Molecular Weight 332 ) Sodium Tripolyphosphate 41.7 (calculated as P205) Moisture 1 . 73 The powder produced was a dust free, free flowing granular agglomerate.
The method enabled a liquid addition of 35.0% W/W to the fluid bed which is comfortably in excess of the limit of 20% imposed by 20 known methods.
Active matter content was as high as 23.3%, which is almost twice the maximum amount of 12% of active matter achieved by known methods, utilising a fluid bed apparatus.
The amount of alkyl aryl sulphonic acid adsorped onto the 25 tripolyphosphate and other alkalies present was well in excess of the previously know adsorptive figures quoted in literature as shown in TABLE A.

, ,. : i : : .

13~327~

In EXAMPLE 1 the theoretical maximum for successful adsorption of alkyl aryl sulphonic acid is calculated to be 15 . 0759 of sulphonic acid per 100 9 of initial powder mixture. The practical result of use of the claimed method is calculated to be 21 . 3119 of sulphonic acid 5 per 1009 of initial powder mixture which is well in excess of the results from previously known methods.
Similarly in EXAMPLE 2 the figures for theoretical maximum and practical results are 19.2269 and 32.3119 of alkyl aryl sulphonic acid per l OOg of initial powder mixture.
Prior art methods of dry neutralisation in whatever apparatus have always assumed the presence of added water and have always restricted the ratio of the amount of alkyl aryl sulphonates -to the amount of alkali to a limit which the invention successfully exceeds.
The present invention provides a cost efficien-t method of producing a 15 high active, non-dusty, free flowing, stable anionic detergent powder which may be easily handled and easily stored.

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Claims (32)

1. A method of producing a free flowing, high active, anionic detergent comprising the step of adsorbing an anionic surfactant acid onto a powdered or granular material to form an agglomerate without the addition of water in the agglomeration stage.
2. A method of producing a free flowing, high active detergent as claimed in claim 1, wherein said material is heated and is substantially dry prior to adsorption of the anionic surfactant acid.
3 A method of producing a free flowing, high active detergent as claimed in claim 1 or claim 2, wherein at least a part of the anionic surfactant acid is adsorbed onto the powdered or granular material in a fluidised bed.
4 A method of producing a free flowing, high active detergent as claimed in claims 1 or 2, wherein the anionic surfactant acid comprises any of the following alone or in combination: alkyl aryl sulphonic acids, fatty acid sulphonic acids, olefin sulphonic acids, fatty alcohol ether sulphuric acid, fatty methyl ester sulphonic acid, alkane sulphonic acids.
5. A method of producing a free flowing, high active detergent as claimed in claims 1 or 2, wherein the anionic surfactant acid comprises any of the following either alone or in combination: alkyl aryl sulphnic acids containing an alkyl group with 9-20 carbon atoms and a sulphonic acid or sulphuric acid ester group, fatty acid sulphuric acids obtained by sulphating alcohols with 8-18 carbon atom chains and linear straight chain alkyl benzene sulphonic acids in which the average number of carbon atoms in the alkyl group is from 11 to 13.
6. A method of producing a free flowing, high active detergent as claimed in claims 1 or 2, wherein the amount of anionic surfactant acid is in the range from 12% to 40% by weight based on the weight of the final product.
7. A method of producing a free flowing, high active detergent as claimed in claims 1 or 2, wherein the amount of anionic surfactant acid is in the range from 12% to 35% by weight based on the weight of the final product.
8. A method of producing a free flowing, high active detergent as claimed in claims 1 or 2, wherein the amount of anionic surfactant acid is in the range from 12% to 30% by weight based on the weight of the final product.
9. A method of producing a free flowing, high active detergent as claimed in claims 1 or 2, wherein said powdered or granular material comprises alkaline material.
10. A method of producing a free flowing, high active detergent as claimed in claims 1 or 2, wherein said powdered or granular-material comprises solely or in combination with other ingredients, a phosphate, carbonate, bicarbonate, sulphate or silicate salt of an alkali metal or an alkaline earth metal.
11. A method of producing a free flowing, high active detergent as claimed in claims 1 or 2, wherein the amount of powdered or granular material is in the range from 60 to 95% by weight based on the weight of the final product.
12. A method of producing a free flowing, high active detergent as claimed in claims 1 or 2, wherein said method further comprises the coating of said agglomerate with a silicate.
13. A method of producing a free flowing, high active detergent as claimed in claims 1 or 2, wherein said method further comprises the coating of said agglomerate with an alkali, or an alkaline salt.
14. A free flowing, high active anionic detergent prepared by the method as claimed in claims 1 or 2.
15. A free flowing, high active, anionic, powdered or granular detergent composition comprising an anionic surfactant acid adsorped onto a powdered or granular material wherein at least 96% by weight of said detergent composition has a particle size distribution substantially within the range from 250 microns to 1700 microns.
16. A free flowing, high active, anionic powdered or granular detergent composition as claimed in claim 15, wherein the anionic surfactant acid is present in the range from 12 to 40% by weight of the total composition and the powdered or granular material is present within the range from 20 to 50% by weight at the total composition.
17. A free flowing, high active, anionic, powdered or granular detergent composition comprising an anionic surfactant acid adsorped onto a powdered or granular material anionic surfactant acid being present in the range from 12 to 40% by weight of the total composition and the powdered or granular material being present within the range from 20 to 50% by weight of the total composition.
18. A free flowing, high active, anionic powdered or granular detergent composition as claimed in claim 17, wherein at least 96% by weight of said detergent composition has a particle size distribution substantially within the range from 250 microns to 1700 microns.
19. A free flowing, high active, anionic, powdered or granular detergent composition as claimed in any of claims 15, 16 or 17, wherein said detergent composition has an average particle size substantially in the range from 1100 to 1300 microns.
20. A free flowing; high active, anionic, powdered or granular detergent composition as claimed in any of claims 15, 16 or 17, wherein said detergent composition has an untapped bulk density in the range from 600 to 720 gm/ml.
21. A free flowing, high active, anionic powdered or granular detergent composition as claimed in any of claims 15, 16 or 17, wherein said detergent composition has a tapped bulk density in the range from 730 to 830 gm/ml.
22. A free flowing, high active, anionic, powdered or granular detergent composition as claimed in any of claims 15, 16 or 17, wherein said detergent composition has a mositure content less than 4% by weight of the total composition.
23. A free flowing, high active, anionic powdered or granular detergent composition as claimed in any of claims 15, 16 or 17, wherein said detergent composition has an angle of repose within the range from 36° to 41°.
24. A free flowing, high active, anionic, powdered or granular detergent composition as claimed in any of claims 15, 16 or 17, wherein said detergent composition has a sliding angle in the range from 25°
to 28°.
25. A free flowing, high active, anionic powdered or granular detergent composition as claimed in any of claims 15, 16 or 17, wherein said detergent composition has a flowrate in the range from 30 to 41 cc/sec.
26. A free flowing, high active, anionic, powdered or granular detergent composition as claimed in any of claims 15, 16 or 17, wherein said detergent composition has a compressibility in the range from 7 to 15%.
27. A free flowing, high active, anionic powdered or granular detergent composition as claimed in any of claims 15, 16 or 17, wherein the anionic surfactant acid is present in the range from 12 to 30% by weight of the total composition.
28. A free flowing, high active, anionic, powdered or granular detergent composition as claimed in any of claims 15, 16 or 17, wherein said powdered or granular material is present in the range from 30 to 40% by weight of the total composition.
29. A free flowing, high active, anionic powdered or granular deter gent composition as claimed in any of claims 15, 16 or 17, wherein said powdered or granular material comprises alkaline material.
30. A free flowing, high active, anionic, powdered or granular detergent composition as claimed in any of claims 15, 16 or 17 wherein said powdered or granular material comprises any of the following either alone or in combination: a phosphate, carbonate, bicarbonate, sulphate, or silicate salt of an alkali metal or an alkaline earth metal.
31. A free flowing, high active, anionic, powdered or granular detergent as claimed in any of claims 15, 16 or 17, wherein said anionic surfactant acid comprises any of the following alone or in combination:
alkyl aryl sulphonic acids, fatty acid sulphonic acids, olefin sulphonic acids, fatty alcohol ether sulphuric acid, fatty methyl ester sulphonic acid, alkane sulphonic acids.
32. A free flowing, high active, anionic powdered or granular detergent composition as claimed in any of claims 15, 16 or 17, wherein said anionic surfactant acid comprises any of the following ether alone or in combination: alkyl aryl sulphonic acids containing an alkyl group with 9-20 carbon atoms and a sulphonic acid or sulphuric acid ester group, fatty acid sulphuric acids obtained by sulphating alcohols with 8-18 carbon atom chains, and linear straight chain alkyl benzene sulphonic acids in which the average number of carbon atoms in the alkyl group is from 11 to 13.
CA000607122A 1988-08-05 1989-07-31 Free flowing anionic detergent and a method of production thereof Expired - Fee Related CA1323278C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB888818613A GB8818613D0 (en) 1988-08-05 1988-08-05 Detergents
GB8818613.5 1988-08-05

Publications (1)

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CA1323278C true CA1323278C (en) 1993-10-19

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KR (1) KR920009044B1 (en)
AT (1) ATE97951T1 (en)
CA (1) CA1323278C (en)
DE (1) DE68911053T2 (en)
ES (1) ES2047677T3 (en)
GB (1) GB8818613D0 (en)
HK (1) HK48495A (en)
IE (1) IE63797B1 (en)
IN (1) IN176172B (en)
MY (1) MY105001A (en)
NZ (1) NZ230218A (en)
PT (1) PT91386A (en)
WO (1) WO1990001536A1 (en)

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NZ230218A (en) 1991-11-26
DE68911053D1 (en) 1994-01-13
ATE97951T1 (en) 1993-12-15
KR900701997A (en) 1990-12-05
MY105001A (en) 1994-07-30
GB8818613D0 (en) 1988-09-07
EP0404865A1 (en) 1991-01-02
KR920009044B1 (en) 1992-10-13
EP0353976A1 (en) 1990-02-07
IE63797B1 (en) 1995-06-14
PT91386A (en) 1990-03-08
DE68911053T2 (en) 1994-03-31
HK48495A (en) 1995-04-07
AU622925B2 (en) 1992-04-30
EP0353976B1 (en) 1993-12-01
WO1990001536A1 (en) 1990-02-22
IN176172B (en) 1996-02-17
AU4049289A (en) 1990-03-05
ES2047677T3 (en) 1994-03-01
IE892530L (en) 1990-02-05

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