GB2204609A - Liquid detergent/softener compositions - Google Patents

Liquid detergent/softener compositions Download PDF

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Publication number
GB2204609A
GB2204609A GB08810901A GB8810901A GB2204609A GB 2204609 A GB2204609 A GB 2204609A GB 08810901 A GB08810901 A GB 08810901A GB 8810901 A GB8810901 A GB 8810901A GB 2204609 A GB2204609 A GB 2204609A
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United Kingdom
Prior art keywords
composition according
component
formula
softener
composition
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Granted
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GB08810901A
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GB2204609B (en
GB8810901D0 (en
Inventor
Jean-Pierre Chavannes
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Sandoz AG
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Sandoz AG
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Publication of GB8810901D0 publication Critical patent/GB8810901D0/en
Publication of GB2204609A publication Critical patent/GB2204609A/en
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Publication of GB2204609B publication Critical patent/GB2204609B/en
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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
    • 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
    • C11D1/62Quaternary 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
    • C11D1/38Cationic compounds
    • C11D1/65Mixtures of anionic 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
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/04Carboxylic acids or salts thereof
    • 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
    • C11D1/02Anionic compounds
    • C11D1/04Carboxylic acids or salts thereof
    • C11D1/06Ether- or thioether carboxylic acids
    • 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
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/123Sulfonic acids or sulfuric acid esters; Salts thereof derived from carboxylic acids, e.g. sulfosuccinates
    • 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
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • 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
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/22Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic 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
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/28Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
    • 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
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29Sulfates of polyoxyalkylene ethers

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

1 2204609 IMPROVEMENTS IN OR RELATING TO ORGANIC COMPOUNDS This invention
relates to liquid laundry detergent compositions for use in domestic and industrial laundering.
Such liquid detergents mostly consist of a mixture of anionic and nonionic surfactants, but no builders,.so that their washing power for fatty stains is only moderate despite their high surfactant content Qv 40 %). For good washing effect on protein-containing stains it is also necessary to include enzymes in the formulation.
It has also been attempted to include softeners in liquid detergent compositions, to avoid the need for aftertreatment with a solution or dispersion of a softener. It has however been found that conventional softeners tend to be incompatible with the anionic surfactants which are present so that the composition does not remain as a stable solution, but separates into two phases. When phase separation occurs, the composition must be shaken each time before use, and measurement of the correct dosage becomes unreliable. For this reason, liquid detergent compositions containing softeners have so far been made only on the basis of non-ionic surfactants, which tend to have inadequate washing power.
It has now been found that stable liquid detergent compositions based on anionic surfactants having excellent washing power can be made containing a selected group of softeners. Accordingly, the 1 present invention provides a stable liquid detergent composition based on one or more anionic surfactants, and containing a softener which is the product of acylation and quaternization of a polyalkylene polyamine. Preferred softeners are of formula I R Q 1 R CONH-+ CH J1 N CH 1 NHCOR 1 2 n 1 2/n 1 R xe in which each RI, independently, is C12-19 alkyl or C12-le alkenyl; each n, independently, is 2 or 3; R2 is C1-4 alkyl, C1-4 hydroxyalkyl, or C1-4 hydroxyalkyl etherified with 1-10 ethylene oxide groups; R3 is CI-4 alkyl or benzyl; and XG is a halide, methylsulphate or ethylsulphate anion.
Preferred liquid detergent compositions according to the invention contain I (A) 1-15 X, preferably 3-10% of softener of formula I (B) 0-25 %, preferably 4-20% of a partially carboxymethylated or carboxyethylated ethylene oxide adduct of a fatty alcohol or an alkylphenol (C) 5-30 X, preferably 10-25%, of one or more fatty acids (D) 2-20 %, preferably 5-15% of one or more other anionic surfactants.
All percentages are by weight based on the total weight of the composition, including water. Preferably the active components (A)-(D) together make up 20-50%, preferably 30-50% of the total compositi on.
The composition also contains sufficient alkali to neutralise the anionic components. In.addition the composition may contain other conventional components for example nonionic surfactants, hydrotropes, v 1 sequestering agents, buffers, enzymes and optical brighteners.
The softeners of formula I may be prepared in conventional manner by the reaction of a dialkylene triamine with a fatty acid or a functional derivative thereof, followed by alkylation and quaternisation with an alkyl, hydroxyalkyl or benzyl derivative. Preferred softeners contain at least one hydroxyalkyl group, more preferably a 0-hydroxyethyl group which may be etherified with ethylene oxide groups (preferably 1-5 EO groups), and at least one unsaturated fatty acid residue, for example an oleyl group. Preferably both groups R, are identical, or represent the same average mixture of groups, for example a mixture of 85% oleyl and 15 % stearyl groups.
Component (B) is preferably a compound of formula II R- 0---+ CH2CH20). A - COOH-7 II in which R is the residue of a C8-22 fatty alcohol or of an alkylphenol having 10-24 C atoms; A is a methylene or ethylene group; m is a number from 1-20; and X is an average value from 0.1 to 1.
Compounds of formula II are k,own or may be prepared by conven tional methods from available starting materials. The most preferred component (B) is a compound of formula II obtained by reacting a synthetic lauryl alcohol (C12-15) with 4-5 moles ethylene oxide and subsequently with 0.8 mole chloracetic acid. The compounds are normally used in the form of their alkali metal salts, particularly sodium salts.
The fatty acids of component (C) are preferably saturated and unsaturated CS-22 carboxylic acids, more preferably C12-18. The fatty acids, for example coco fatty acid or oleic acid are added a such and converted to the salt form by addition of alkali e.g. NaOH, KOH or an organic base e.g. triethanolamine.
4 - The further anionic surfactants of component (D) may be any of the following conventional types:
a) sulphates and sulphonates of fatty acids, fatty acid esters and fatty acid amides b) linear or branched C5-18 alkyl sulphates and sulphonates c) sulphated ethoxylated compounds, particularly sulphated forms of any non-ionic surfactants which may be present d) polycarboxylic acid ester sulphates e) C5-18 alkylbenzenesulphonates and C1-4 alkyl and dialkylnaphthalene sulphonates.
These compounds may be added in acid form and converted to their salt forms by addition of alkali.
Nonionic surfactants which may be present include ethylene oxide (E0) 1 propylene oxide (PO) block copolymers (Pluronics), and the addition products of EO or PO, preferably EO, to fatty alcohols, fatty amines, fatty acids, fatty acid alkanolamides and alkylphenols. Such non-ionic surfactants are conventional and commercially available.
Hydrotropic compounds which may be present include for example urea, dicyandiamide and its derivatives, alcohols, water-soluble glycols, glycol ethers and glycol esters and C1-4 alkylbenzenesulphonates, provided that the compounds display no cloud point in distilled water up to 1001. They act so as to prevent phase separation, that is to stabilize the liquid composition.
Sequestering agents include citric acid, nitrilotriacetic acid and other complex formers. Buffers may be used to stabilise the pH of the wash liquor in the neutral or alkali region. Buffer substances include sodium bicarbonate, sodium carbonate and sodium silicate.
By selection of these additional components, and optionally by use of enzymes and optical brighteners, the washing effect of the liquid detergent can be adjusted according to the desired field of use. The liquid detergent compositions of the invention are primarily useful as domestic laundry detergents. Not only do they display good washing power, they also produce a soft handle on laundered cotton goods. Being phosphate-free, they are ecologically acceptable. When used in conjunction with optical brighteners they do not cause quenching of the brightener so that acceptable grades of whiteness are obtained. The liquid compositions are stable and do not separate into two phases on storage.
The following Examples, in which all percentages are percentages by weight of the entire composition, illustrate the invention:
Examples 1-7
In the following examples, component (A) is a compound of the formula CH 2CH 2 OH 1 0 R 1 CONHCH 2CH 2 - N- CH 2 CH 2 NHCOR 1 1 CH 3 CH 3 OSO 3 0 in which R, is a mixture of 85% oleyl groups and 15% stearyl groups, Component (B) is of the formula RO(CH2CH204.5 - (CH2COONa)o.8 in which R is C12-15 alkyl, used in the form of a 67% aqueous paste. The components are added to demineralised water at room temperature, stirring until a homogenous solution is obtained. The final pH of the product is approx. 7. 5. The components.are in the proportions shown in the following Table.
7 - Table
Percentage by weight Example 1 2 3 4 5 6 7 Component Demineralised water 12.5 16.0 13.5 14.0 (A) softener 5.0 7.0 7.0 5.0 (B) Carboxymethylated adduct (67%) coco fatty acid oleic acid (C) (C) (C) dodecylbenzene sulphonic acid (D) lauryl ether sulphate lauryl alcoholpoly (7)ethylene-glycol ether (SANDOXYLATE A 25-7) triethanolamine 10.0 diethanolamine - caustic soda (30% aq)15.0 isopropanol 12.0 ethylene glycol - optical brightener 1.0 citric acid 2.5 10.0 10.0 - 10.0 20.0 15.0 15.0 20.0 5.0 5.0 5.0 5.0 7.0 8.0 11.0 3.5 3.5 7.0 27.8 34.5 7.0 5.0 10.0 8.0 15.0 10.0 5.0 8.0 6.0 3.5 3.0 33.5 6.0 5.0 6.0 4.0 6.0 3.0 7.5 - - 3.0 10.0 10.0 5.0 12.5 14.5 12.0 12.0 10.7 14.0 14.0 18.5 12.0 12.0 810 8.0 0.5 3.0 1.0 1.0 1.0 1.0 2,5 8.0 8.0 0.5 3.0 Application Example A The compositions of Examples 1-7 are tested on cotton samples bleached without optical brightener. The washing tests are carried out with 2 kg polyester as ballast in a Schulthess Super 45 (Trade Mark) washing machine on programme 4. The washing conditions are as follows:
1 - 8 cylinder volume 43 1 amount of wate 17 1 amount of detergent 8 g11 temperature 600C heating time about 11 min.
washing time about 15 min.
water hardness 18dH pH of the wash liquor 7.
After washing the effect of the detergent composition on the cotton samples is measured by means of a spectrophotometer (Datacolor Type 7080) and expressed as the CIE whiteness degree (CIE publication No. 15.2).
il 1 1 J e

Claims (14)

CLAIMS: -
1. A stable liquid detergent composition based on one or more anionic surfactants, and containing a softener which is the product of acylation and quaternization of a polyalkylene polyamine.
2. A composition according to Claim 1 in which the softener is of formula I R 01 R CONH---+ CH N -----+ CH2,--NHCOR 1 1 n R 3 xe in which each R,, independently, is C12-1e alkyl Or C12-18 alkenyl; each n, independently, is 2 or 3; R2 is C1-4 alkyl, C1-4 hydroxyalkyl, or C1-4 hydroxyalkyl etherified with 1-10 ethylene oxide groups; R3 is C1-4 alkyl or benzyl; and X- is a halide, methylsulphate or ethylsulphate anion.
3. A composition according to Claim 2 containing I (A) 1-15 % of softener of formula I (B) 0-25 % of a partially carboxymethylated or carboxyethylated ethylene oxide adduct of a fatty alcohol or an alkylphenol (C) 5-30 % of one or more fatty acids (D) 2-20 % of one or more other anionic surfactants, by weight based on the total weight of the compos.ition, including water.
4. A composition according to Claim 3 containing 3-10 % of component 4-20 % of component 10-25 % of component (A) (B) (C) and 5-15 % of component (D) by weight based on the total weight of the composition, including water.
5. A composition according to Claim 4 in which the active components (A)(D) together make up 30-50% by weight of the composition.
6. A composition according to any one of Claims 2-5 in which the softener (A) is a compound of formula I in which R2 is a 0-hydroxyethyl group or a 0-hydroxyethyl group etherified with 1-5 ethylene oxide groups.
7. A composition according to Claim 6 in which the softener (A) is a compound of the formula CH 2 CH 2 OH R CONHCH CH 0 CH CH NHCOR 1 2 2_ N 2 2 1 1 CH 3 CH 3 OSO 3 c) in which R, is a mixture of 85% oleyl groups and 15% stearyl groups.
8. A composition according to any one of the Claims 3-7 in which component B is a compound of formula II R - 0 __C CII 2 CH 2 0) m ( A - COOH II in which R is the residue of a C8-22 fatty alcohol or of an alkylphenol having 10-24 C atoms; A is a methylene or ethylene group; m is a number from 1-20; X is an average value from 0.1 to 1.
and
9. A compound according to Claim 8 in which component (B) is a compound of formula II obtained by reacting a synthetic lauryl alcohol (C1215) with 4-5 moles ethylene oxide and subsequently with 0.8 mole chloracetic acid.
10. A composition according to any one of Claims 3-9 in which component (C) is a saturated or unsaturated C12-18 carboxylic acid.
11. A composition according to any one of Claims 3-10 in which component (D) is selected from a) sulphates and sulphonates of fatty acids, fatty acid esters and fatty acid amides b) linear or branched C5-18 alkyl sulphates and sulphonates c) sulphated ethoxylated compounds, d) polycarboxylic acid ester sulphates and e) C5-18 alkylbenzenesulphonates and C1-4 alkyland dialkylnaphthalene sulphonates.
12. A composition according to any one of the preceding claims containing additionally one or more components selected from non-ionic surfactants, hydrotropes and sequestering agents.
13. A composition according to any one of the preceding claims containing an optical brightener. j
14. A composition as described in any one of the Examples.
Published 1988 at The Patent Office, State House, 66."71 High Holborn, London WCIR 4TP. Further copies may be obtained from The Patent Office, Wes Branch, St Mary Cray, Orpington, Kent BR5 3RD. Printed by Multiplex techniques ltd, St Mary Cray, Kent. Con. 1/87.
GB8810901A 1987-05-11 1988-05-09 Liquid detergent/ softener compositions Expired - Lifetime GB2204609B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE3715636 1987-05-11

Publications (3)

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GB8810901D0 GB8810901D0 (en) 1988-06-15
GB2204609A true GB2204609A (en) 1988-11-16
GB2204609B GB2204609B (en) 1991-03-06

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GB8810901A Expired - Lifetime GB2204609B (en) 1987-05-11 1988-05-09 Liquid detergent/ softener compositions

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JP (1) JPS63292000A (en)
CH (1) CH676007A5 (en)
FR (1) FR2615202B1 (en)
GB (1) GB2204609B (en)
IT (1) IT1234993B (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1989009204A1 (en) * 1988-04-02 1989-10-05 Henkel Kommanditgesellschaft Auf Aktien Quaternary ammonium compounds
EP0376893A2 (en) * 1988-12-30 1990-07-04 Sandoz Ag Liquid laundry detergent compositions containing optical brighteners
WO1995029217A1 (en) * 1994-04-25 1995-11-02 The Procter & Gamble Company Stable, aqueous laundry detergent composition having improved softening properties
WO1997012020A1 (en) * 1995-09-29 1997-04-03 The Procter & Gamble Company Liquid laundry detergents containing selected alkyl amidoalkoyl quaternary ammonium compounds
WO2012172367A1 (en) * 2011-06-17 2012-12-20 Reckitt Benckiser N.V. Composition
WO2013087285A1 (en) * 2011-12-12 2013-06-20 Unilever Plc Laundry compositions and uses

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH540071D (en) * 1971-04-14
US4460485A (en) * 1983-07-15 1984-07-17 Lever Brothers Company Polyester fabric conditioning and whitening composition
GB8430301D0 (en) * 1984-11-30 1985-01-09 Swan Thomas & Co Ltd Compositions of matter for fabric softeners
US4622173A (en) * 1984-12-31 1986-11-11 Colgate-Palmolive Co. Non-aqueous liquid laundry detergents containing three surfactants including a polycarboxylic acid ester of a non-ionic

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1989009204A1 (en) * 1988-04-02 1989-10-05 Henkel Kommanditgesellschaft Auf Aktien Quaternary ammonium compounds
EP0336267A2 (en) * 1988-04-02 1989-10-11 Henkel Kommanditgesellschaft auf Aktien Quaternary ammonium compounds
EP0336267A3 (en) * 1988-04-02 1989-10-25 Henkel Kommanditgesellschaft auf Aktien Quaternary ammonium compounds
EP0376893A2 (en) * 1988-12-30 1990-07-04 Sandoz Ag Liquid laundry detergent compositions containing optical brighteners
EP0376893A3 (en) * 1988-12-30 1991-08-07 Sandoz Ag Liquid laundry detergent compositions containing optical brighteners
WO1995029217A1 (en) * 1994-04-25 1995-11-02 The Procter & Gamble Company Stable, aqueous laundry detergent composition having improved softening properties
US5622925A (en) * 1994-04-25 1997-04-22 The Procter & Gamble Company Stable, aqueous laundry detergent composition having improved softening properties
WO1997012020A1 (en) * 1995-09-29 1997-04-03 The Procter & Gamble Company Liquid laundry detergents containing selected alkyl amidoalkoyl quaternary ammonium compounds
WO2012172367A1 (en) * 2011-06-17 2012-12-20 Reckitt Benckiser N.V. Composition
WO2013087285A1 (en) * 2011-12-12 2013-06-20 Unilever Plc Laundry compositions and uses

Also Published As

Publication number Publication date
GB2204609B (en) 1991-03-06
FR2615202A1 (en) 1988-11-18
IT8847907A0 (en) 1988-05-03
JPS63292000A (en) 1988-11-29
GB8810901D0 (en) 1988-06-15
FR2615202B1 (en) 1994-03-11
IT1234993B (en) 1992-06-16
CH676007A5 (en) 1990-11-30

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Effective date: 19940509