GB2185992A - Liquid softening detergent composition containing alkyl glycoside - Google Patents
Liquid softening detergent composition containing alkyl glycoside Download PDFInfo
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- GB2185992A GB2185992A GB08701854A GB8701854A GB2185992A GB 2185992 A GB2185992 A GB 2185992A GB 08701854 A GB08701854 A GB 08701854A GB 8701854 A GB8701854 A GB 8701854A GB 2185992 A GB2185992 A GB 2185992A
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0084—Antioxidants; Free-radical scavengers
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/662—Carbohydrates or derivatives
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/86—Mixtures of anionic, cationic, and non-ionic compounds
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- 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
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-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
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/29—Sulfates of polyoxyalkylene ethers
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/72—Ethers of polyoxyalkylene glycols
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups
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- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Detergent Compositions (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
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Abstract
Liquid detergent compositions having softening and detergency properties comprise an alkyl glycoside, a quaternary ammonium compound, a nonionic surfactant and an anionic surfactant as the four essential ingredients; and a method of simultaneously cleaning and softening, without reducing brightener and detergency performance, comprises treating fabrics with the compositions in the wash cycle of the laundering operation.
Description
SPECIFICATION
Liquid softergent having improved detergency containing alkyl glycoside
The present invention relates to novel liquid detergent compositions to be used in the laundering offabrics, comprising an alkyl glycoside in an amount effective to improve cleaning efficacy and to provide improved softening properties in the presence of quaternary ammonium softening compounds and anionic and nonionic surfactants. Such compositions are also referred to by the term "softergent".
The use of various and diverse chemical materials and particularlycationicquaternaryammonium compounds as softeners fortextile products is very well known in the art. It is also well known to employ such materials for their softening effects during the laundering operation and particularly in the rinse cycle of the laundering process. This lattertechnique has been necessitated by the fact that the aforesaid quaternary compounds heretofore employed, being mainly cationic in nature, were not compatible with the anionic detergents, one of the major types of detergents used in the washing cycle. Furthermore, cationic quaternary compounds are relatively ineffective in the presence of nonionic detergents.
It is also well known thatthere is a tendencyforlaundered articles to yel low or discolourwhen treatedwith the aforesaid quaternary compounds.
Another disadvantage associated with the use of the said cationic agents in the laundering offabrics therewith is its interference with the deposition on the fabrics of optical brighteners, thereby reducing optical brightener performance of a detergent composition containing the said optical brighteners.
Still another disadvantage ofthe cationic quaternary ammonium antistatic softener is its interference with the cleaning properties ofthe detergent by reducing the soil removal effected by the detergent, resulting in decreased washing effectiveness. The presence of the anionic detergent material substantially negates the fabric softening properties ofthe cationic quaternary ammonium compounds.
Accordingly, the aforesaid quaternary agents have been combined with a variety of compounds designed to counteract the adverse detergency properties thereof, or the said quaternary softening agents have been replaced by other softening agents to improve cleaning efficacy.
Higher alkyl mono- and poly-glycosides useful as detergents, textile softeners, surfactants, gelling agents, food emulsifiers and lubricants; and processesfortheir preparation have been disclosed in US PatentNos.
3,598,865; 3,707,535; 3,839,318; 3,772,269; and 3,219,656.
Higher alkyl polyglycosides have been used as nonionic surfactants in a variety of detergentcompositions in conjunction with anionic surfactants as shown in US Patent Nos. 3,721,633; European Patent Nos.
0.070,074; 0,070,075; 0,070,076; 0,092,877; and in conjunction with an anionic and another nonionic surfactant as shown in US Patent Nos. 4,483,779; 4,483,780; 4,483,787; European Patent Nos. 0,075,994; 0,075,995; 0,075,996 and 0,105,556 to provide good detergency.
The prior art also discloses detergent compositions containing an alkyl polyglycoside, a conventional nonionic sufactant and a cationicfabric-softener compound to provide both softening and detergency properties during laundering, as shown in US Patent No.4,493,773; European Patent Nos. 0,094,118 and 0,106,692. However,these patents expressly omit anionic surfactants as being detrimental to the composition.
US Patent No.4,014,808 discloses an aqueous detergent composition for cleaning hard surfaces such as floors, comprising alkaline builders, a mixture of higher alkyl mono and polyglycosides, a nonionic ethoxylate or any anionic modified ethoxylate in acid form, and a cationic flocculant such as polydiallyldimethyl ammonium chloride which causes soilageto agglomerate into flocs which float, and optionally a floatation agent which is sodium alkylaryl sulphonate.
However, none of the cited prior art references discloses a liquid detergent (or softergent) composition for simultaneously cleaning and softening fabrics comprising four essential ingredients, an effective amount of an alkyl glycoside to improve detergency efficacy and softening properties in the presence of a quaternary ammonium softening compound and anionic and nonionic surfactants.
We have now discovered that the addition of an alkyl polyglycoside surfactantto a liquid detergent(or softergent) formula containing a cationic quaternary softening compound in a nonionic-anionicsurfactant system boosts detergency and provides increased softening properties to fabrics treated therewith.
Accordingly, the present invention aims to provide a liquid detergent composition having improved cleaning efficacy in the presence ofcationic quaternary ammonium softening compounds.
The invention also aims to provide a liquid detergent composition, that simultaneously cleanses and softens fabrics during the laundering process comprising an alkyl glycoside, a quaternaryammonium softening compound, a nonionic surfactant and an anionic surfactant as the four essential ingredients.
The invention further aims to provide a liquid detergent (or softergent) formulation having improved cleaning and softening properties, duetothe presence of an alkyl glycoside in a detergent composition containing a mixture of anionic, nonionic and cationic surfactants.
According to the present invention, a liquid detergent (of softergent) composition for laundering fabrics comprisesfouressential ingredients, namely an effective amount of an alkyl glycoside to improve detergency efficacy and softening properties in the presence of a quaternary ammonium softening compound, an anionic surfactant and a nonionicsurfactant. The invention also extends to a method of simultaneously cleansing and softening fabrics without reducing brightener and detergency performance which comprises treating fabrics with a composition in accordance with the present invention during the wash cycle ofthe laundering operation.
More specifically, the present invention relates two a stable liquid detergent (or softergent) composition, comprising a C1-C30 alkyl mono- or polyglycoside in an amount sufficient to overcome the decrease in detergency efficacyduetothe quaternary ammonium compound and constitutes about 2 to 25% byweight, about2to 8% by weight ofa quaternaryammonium softening compound, about8to 25% byweight ofa nonionicsurfactant, and about 1 to 12% byweightofan anionicsurfactant, in an aqueous carrier.
The alkyl glycosides function as a softening agent and boosts fabric softening in the presence of cationic surfactants. It is believed thatthe alkyl glycosides coat the surface of the fabric and/or alterthefabric structure, thereby imparting softening benefits. It is believed that the alkyl glycosides may disrupt hydrogen-bonding, thereby increasing softening properties. The alkyl glycosides do not interfere with deterency and/or brightener deposition which is another problem of softergents.
The alkyl glycosides, utilized in the compositions of the present invention may be defined as having one or more hydrophobic groups containing 1 to 30 carbon atoms per hydrophobic group, and preferably 8to 15 carbon atoms, and a hydrophilic glycoside group containing 1 to about 10, and preferably from about 1 to 3 saccharide radicals. The alkyl glycosides may be represented by the following formula: RO(R'O)XZn, wherein R represents a C1-C30 alkyl radical, (R'O) represents an ethoxy, propoxy orglyceryl group,X hasa numerical value of0-10 and preferablyO,Z is a reducing saccharide containing 5 or 6carbon atoms, and n has a numerical value of 1-10 and preferably 1.Oto 3.The hydrophobic alkyl group may be saturated orunsaturated, branched orstraightchain, preferablysaturated and linear, containing 1 to 30 carbon atoms, preferably 8 to 23, carbon atoms. Suitable alkyl polyglycosides include methyl, ethyl, propyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyI, hexadecyl, heptadecyl, octadecyl and mixtures thereof, and monoglycosides, diglycosides, triglycosides. The glycoside units may be glucose, galactose, mannose, lactose and/orfructose. Methods of preparing the aforesaid glycosides are disclosed in US Patent
Nos. 3,598,865; 3,707,535; 3,839,318; 3,772,269; 3,219,656, all ofwhich are incorporated herein by reference.
The addition ofthe alkyl glycosideto the detergent (or softergent) improves the cleaning efficacy thereof. The amount of glycoside should be sufficient to counteract the loss in detergency due to the presence ofthe cationic quaternary ammonium softening agents in the softergent. Accordingly, the g lycoside content improves detergency in the softergent composition, and constitutes about 1 to 30% and preferably 2 to 25% by weight of the composition.
The cationic quaternary softening agents are commercially well known and include quaternary ammonium compounds wherein typically at least one of the four groups linked to the nitrogen atom is an alkyl group of about 10-20 carbon atoms and at leasttwo of the groups linked to the nitrogen atom arealkyl groups which contain 1-3 carbon atoms and the fourth group may be eitheranotherC10- C20 alkyl group ora C1 - C3 alkyl group, and there is present an anion such as halogen, acetate, or methosulphate.Typical quaternary ammonium compounds are ethyl-dimethyl-stearyl ammonium chloride, trimethyl-stearyl ammonium chloride,timethylcetyl ammonium bromide, dimethyl-ethyl-dilauryl ammonium chloride, methyl-ethyl-dilauryl ammonium chloride, dimethyl-ethyl-lauryl ammonium chloride, dimethylpropyl-myristyl ammonium chloride, tallowtrimethyl ammonium chloride, di hydrogenated tallow dimethyl ammonium chloride, dicocodimethyl ammonium chloride, distearly dimethyl ammonium chloride, octadecyl trimethyl ammonium chloride, dodecyl trimethyl ortriethylammonium chloride, and the corresponding methosulphates and acetates. Other suitable quaternary compounds include duoquats, imidazolinium quats, polyethoxylated quats, and amidoalkoxylated quats.
In accordance with the present invention, the nonionic surfactants for use as the fabric detergent are commericallywell known and include the primary aliphatic alcohol ethoxylates, alkylphenol ethoxylates and the alcohol ethylene oxide-propylene oxide consensates such as Plurafacs (Wyandotte), and mixtures thereof. The nonionic synthetic organic detergents are generally the condensation product of an organic aliphatic or alkyl aromatic hydrophobic compound and hydrophilic ethylene oxide groups. Practically any hydrophobic compound having a carboxy, hydroxy, amido, or amino group with a free hydrogen attached to the nitrogen can be condensed with ethylene oxide or with the polyhydration product thereof, polyethylene glycol, to form a nonionic detergent.Further, the length ofthe polyethenoxy chain can be adjusted to achieve the desired balance between the hydrophobic and hydrophilic elements.
The nonionic detergents include the polyethylene oxide condensate of one mole of alkyl phenol containing from about 6 to 12 carbon atoms in a straight-or branched-chain configuration with about 5 to 30 moles of ethylene oxide, for example, nonyl phenol condensed with 9 moles of ethylene oxide, dodecyl phenol condensed with 15 moles of ethylene oxide. Condensation products ofthe corresponding alkyl thiophenols with 5to 30 moles of ethylene oxide are also suitable.
Also included in the nonionic detergent class are the condensation products of a higher alcohol (e.g. an alkanol containing about 8 to 18 carbon atoms in a straight or branched-chain configuration) condensed with about 5to 30 moles of ethylene oxide, for example, lauryl-myristyl alcohol condensed with about 16 moles of ethylene oxide.
A preferred group of nonionic surfactants are the Neodol ethoxylates (Shell Co.), which are higher aliphatic alcohol ethoxylates having about 5 to 20 ethyleneoxy groups per mole of aliphatic alcohol containing about 10-18 carbon atoms, such as C12-C13 alkanol condensed with 6.5 moles ethylene oxide, C12-C15 alkanol condensed with 12 moles ethylene oxide, C14-C15 alkanol condensed with 13 moles ethylene oxide, and the like. Ethoxamers having a HLB (hydrophobic lipophilic balance) value of about 8-15 give good O"W (oil in water) emulsification, whereas ethoxamers with low HLB values (below 8) contain less than 5 ethylenoxy groups, and are poor emulsifiers and poor nonionic detergents.This nonionicsurfactant is presentinthe detergent (orsoftergent) composition in accordance with the present invention in an amount equal to or greaterthan the alkyl polyglycoside content, and about8- 25% by weight. The total amount ofnonionic surfactant, namely the glycoside, which is also a nonionic surfactant, and the nonionic alcohol ethoxylates defined above constitutes the major detergent component in this detergent (or softergent), about 25-40% and preferably 30- 40% by weight of the composition.
The anionic surfactants utilized in the detergent (of softergent) compositions of the present invention are commercially well known and include alkylbenzene-sulphonic acid and its salts, e.g. compounds of the formula alkyl-phenyl-SO3.M, wherein alkyl is an alkyl radical of Cs to C22 and preferablyC10to C18 and M is hydrogen or an alkali metal, which compounds comprise a well-known class of anionic detergents and include sodium dodecyl-benzene sulphonate, potassium dodecylbenzene-sulphonate, sodium laurylbenzene-sulphonate, and sodium cetylbenzene sulphonate.Others include paraffin suiphonates, alkyl sulphates, alcohol ether sulphates, olefin sulphonates and the alkylphenolethoxylate sulphates (e.g.sodium dinonylphenoxynonaethoxyethanol sulphate), and other equivalent water-soluble salts, particularly ofthe alkali metal series.
Among the above-noted alkylbenzene-sulphonic acids and salts thereof, the preferred compounds include those which are biodegradable and which are particularly characterised by a linear alkyl substituentoffrom C to C22 and preferably from C12 to C15. It is, of course, understood that the carbon chain length represents, in general, an average chain length since methods for producing such products usually employsalkylating reagents of mixed chain length.It is clear, however, that substantially pure olefins as well as alkylating compounds used in othertechniques can and do give alkylated benzenesulphonateswhereinthe alkyl moiety is substantially (i.e. at least 99%) of one chain length, i.e. C12, C13, C14, or C15. The linear alkyl benzene sulphonates are further characterized by the position of the benzene ring in the linear alkyl chain with any of the position isomers (i.e. alpha to omega) being operable and contemplated.
In addition to the benzene sulphonates one may also employ the lower alkyl (C1 to C4) analogs of benzene such as toluene, xylene, the trimethyl benzenes, ethyl benzene, isopropyl benzene and the like. The sulphonates are generally employed in thewatersoluble saitform which include as the cation,thealkali metals, ammonium and lower amine, and alkanolamine cations.
Examples of suitable linear alkyl benzene sulphonates include:
sodium n-decyl benzene sulphonate
sodium n-dodecyl benzenesulphonate sodium n-tetradecyl benzene sulphonate
sodium n-pentadecyl benzenesulphonate sodium n-hexadecyl benzenesulphonate and the corresponding lower alkyl substituted homogues of benzene as well as the salts of the cations previously referred to. Mixtures of these sulphonates may, of course, also be used with mixtures which may include compounds wherein the linear alkyl chain is smaller or largerthan indicated herein provided that the average chain length in the mixture conforms to the specific requirements of Canto C22.
The linear paraffin sulphonates are also awell-known group of compounds and include water-soluble salts (alkali metal, amine, alkanolamine, and ammonium) of:
1-decane sulphonic acid
1-dodecane sulphonic acid
1 -tridecane sulphonic acid 1-tetradecane sulphonic acid
1-pentadecanesulphonicacid 1-hexadecane sulphonic acid as well as the other position isomers ofthe sulphonicacid group.
In addition to the paraffin sulphonates illustrated above, others with the general range of C,0 to C22 al kyls may be used, with the most preferable range being from C12 to C20.
The linear alkyl sulphates which are contemplated for use in compositions in accordance with the present invention comprise the range of C10 to C20. Specific examples include sodium n-decyl sulphate; sodium n-dodecyl sulphate; sodium n-hexadecyl sulphate, sodium n-heptadecyl sulphate; sodium n-octadecyl sulphate; and the ethoxylated (1 to 100 moles ethylene oxide) derivatives such as the ethoxylated alcohol sulphates, and, of course, the other water-soluble salt-forming cations mentioned above.
Included in the group of anionic detergents, which have been described above as suitable for use in the present invention, are the olefin sulphates, including long chain alkene suiphonates, long chain hydroxyalkane sulphonates, aswell as disulphonates. Examples of suitable oiefin sulphonates, which are merely illustrative of the general class, are sodium dodecenyl-1 sulphonate, sodium tetradecenyl-1 sulphonate, sodium hexadecenyl-1 sulphonate, and sodium octadecenyl-1 sulphonate. The amount of anionic surfactant utilized in the compositions of the present invention is less than the nonionic (ethoxylated aliphatic alcohol) surfactant content by weight, and preferably less than 50% by weight of the total nonionic surfactant (alkylglycoside plus ethoxylated aliphatic alcohol) content, and constitutes about 1 - 12 % by weight of the composition.
The detergent (or softergent) compositions ofthe present invention may also include conventional iau ndering add itives such as optical brig hteners, germicides, soil suspending agents, antiredisposition agents, antioxidants, colouring materials (dyes and pigments), perfumes, water-soluble alcohols, foam boosters, hydrotropes such as sodium and potassium xylene sulphonates, sodium and potassium toluene sulphonates, cumene sulphonates, ethyl benzene sulphonate and the like, enzymes and enzyme stabilizers, provided they do not interfere with the detergency and softening activity of the composition.
The invention may be put into practice in various ways and a number of specific embodiments will be described to illustrate the invention with reference to the accompanying examples.
Example 1
A composition is made up having the ingredients and proportions given in Table 1 below.
Table 7
15% C12- C15 alcohol: 7 mols ethylene oxide
15% alkyl polyglycoside, C12- C13: 3 mols glycoside
(Staley Industrial Products)
0.25% triethanolamine 8.0% monoalkyltrimethyl ammonium chloride
12% C12- C15 alcohol: 3 molls ethylene oxide
sulphate, sodium 4.0% sodium xylene sulphonate 0.5% brightener
Q.S. water
Note on Table 1 1. tailowtrimethyl ammonium chloride
The liquid detergent is prepared by mixing the above ingredients until homogeneous to form a stable
liquid composition.
The detergency of this productwas tested in a tergotometer containing 1 litre of 150 ppm (calcium) water at 120"F ( "C) and 70"F ( C), with a concentration of0.18% softergent, and compared to commercial detergent products which do not contain the alkyl g lycoside ingredient. Afabric load of standard soiled swatches of Test Fabric nylon (TFN) and cotton (TFC), a 65-35% blend of polyester-cotton (PC) and 50:50% dacron :cotton (DC) and EMPA 101 Cloth, was washed with the test detergents and dried in electric tumble dryers. Reflectance ofthe solid swatches are read as a measure of detergency (Rd).The soil removal (SR) is the sum total of the Rd readings on all the swatches, and the soil removal index (SRI) is the average ofthe total Rd readings divided by the numberof swatches. These results are given in Table 2 below.
Table2
Dynamo SOLO Ex. 1 Liq. TIDE BOLD3 120"F 212.5 202.2 220.9 219.5 181.3
SR Total 70"F 194.5 183.3 198.7 202.5 193.8 SR Total Example 1 exhibits superior detergency to Dynamo, Solo and Bold 3. No statistically significant difference in detergency was observed between Ex. 1 and Liquid Tide at 120"F and 70"F.
Sebum soil removal test results are given in Table 3 below. Sebum soil removal at 1 20"F was equal to
Liquid TIDE on cotton and D/C 50/50 and better than most competitors on D/C 50/50. At 70"F Liquid TIDE was slightly better while most other competitors were equal to Ex. 1.
Table3 120 FSEBUMSOIL REMOVAL
Dynamo SOLO Ex. 1 Liq. TIDE BOLD3
Cotton 75.3 71.5 76.5 74.0 72.3
D/C 50/50 67.8 66.5 70.6 71.2 62.4 T0 FSEBUM SOIL REMOVAL
Cotton 76.4 71.9 76.2 80.5 73.3
D/C 50/50 68.0 65.2 68.2 70.4 65.5
A Multistain test at 1 200Fand 70"F gave the following results given in Table 4, using Liquid TIDE asthe control.
Table4 120 F Ex. 1 SOLO BOLD3
Significant wins 2 1 0
Not significant 7 7 2
Significant losses 13 14 20 70"F Significant wins 5 3 0
Not significant 9 3 5
Significant losses 8 16 17 120 F Ex. 1 Liq. TIDE SOLO BOLD3 Total Rdforall 22 Swatches 1407 1502 1368 1202 70"F Total Rdforall 22 Swatches 1351 1390 1240 1215
The most significant losses in detergency as compared to Liquid TIDE were incurred in the case ofthe enzyme at 120"F. This was to be expected since the Ex. 1 formulation contains no enzymes. However, losses were also observed with the oxidizable stains (grape juice and cranberry juice). Ex. 1 showed strong gains on
DDK in case of oily soils (Barbecue Sauce and French Dressing).
At 700F losses due to enzyme stains were considerably reduced. This is dueto the fact that enzymes in general are more effective at highertemperatures. At 700F Ex. 1 is much more effective detergentthan Liquid
TIDE in the case of oil soils (Spangler Sebum/Particulate, Barbecue Sauce, Red Crisco Shortening and French
Dressing).
BOLD 3 and SOLO did not perform better at any temperature.
The five cycle softening/static/brightenertest gave the results set out in Table5 below.
Flourescence of the cotton swatches is read as a measure of brightener effectiveness (Rb).
Table 5
Rb reading Vex. 1 269.94
Liquid TIDE 255.44
SOLO 120.80
DYNAMO 245.53 BOLD 3 224.56
The formulation of Ex. 1 was equal to BOLD 3 in controlling static cling and better than SOLO. Ex. 1 was rated somewhat less effective in softening as compared to SOLO, but showed improved softening as compared totheformulation of Ex. 1 minus the alkyl glycoside.
Example 2
A detergent (or softergent) composition having the ingredients and proportions given in Table 6 is made up.
Table6
21% Neodol 25-71
6% Sodium dodecyl benzene sulphonate
4% tallowtrimethylquaternaryammoniumsulphate 2% Methyl glycoside 0.4% Brightener
8% Ethanol
5% Sodium xylene sulphonate
0.5% Colour
Q.S. Water
Note on Table 6
1 C12- C15 alcohol: 7 moles ethylene oxide.
Examples 3A to 3E
A detergent (of softergent) composition having the ingredients and proportions given in Table 7 is made up.
Table7
21% Neodoi 25-71
4% Sodium dodecyl benzenesulphonate 4% tallowtrimethyl quate4rnary ammonium sulphate
2% Methyl glycoside 0.4% Brightener
8% Ethanol
5% Sodium xylene sulphonate
0.5% Colour
Q.S. Water
Adding 3% of a tallow amine:15 ethylene oxidetothisformulation reduces the softness rating to 6.0.
Omitting the quaternary compound and increasing the methyl glycoside to 6% increases the softness rating 7.2.
Thefollowing Tables 8Ato 8C summarise the brightening and static results of the 5-cycle softening/static/brightenertests on 5 test products and 2 controls.
Table 8A
Products: CONTROL
Product 7.
DYNAMO SOLO LlO.DET.6/6 Static Moderate Light Very
Control to Heavy v. Light Light
Brightening 1stwash 188.5 102.9 214.7 3rd wash 223.1 95.9 240.4 5th wash 209.7 90.5 222.4
Softness 1 10 5.9
SRI - 171.5 186.1
Table 8B
Products: Product 2. Product 3.
Liq. Det. 5/5/6E Soft. 4/4/3E/2MG
Static control Lightvlight Very light
Brightening 1stwash 211.1 216.3 3rd wash 228.2 241.9 5th wash 228.9 237.4
Softness 5.8 6.0
SRI 190.2 186.6
Table 8C Products: Pro duct 4. Pro duct 5.
Soft. 4/42MG Soft. 4/0/6MG
Static control Light vlight Moderate heavy
Brightening 1st wash 227.1 228.5 3rd wash 253.2 254.2 5th wash 251.4 257.0
Softness 6.8 7.2
SRI 193.4 184.1
Notes on Tables 8A to 8C Product
No.
1. 6% dodecylbenzene sulphonate (DBS)/6%tallowtrimethyl quat (quat) 2. 5% DBS/5% quat/6% tallow amine :15 ethylene oxide (TAEO) 3. 4% DBS/4% quat/3% TAEO/2% methyl giycoside (MG) 4. 4% DBS/4% quat/2% MG
5.4% DBS/0% quat/6% MG
The above results indicate that methyl glycoside imparts softening benefits to fabric. The lab tests also indicate that the glycoside imparts brightening benefits in liquid formulations. However, in the absence of quat. no static control is achieved.
The precise composition of Examples 3Ato 3E is set out in Table 9 below.
Table 9
PRODUCT 1 2 3 4 5
Example 3B 3C 3D 3A 3E Parts % Ingredients
Neodol 21 21 21 21 21 'DBS' 6 5 4 4 4 quat2 6 5 4 4 TAEO3 6 3 -
MG4 - - 2 2 6
Brightener 0.4 0.4 0.4 0.4 0.4
Ethanol 8 8 8 8 8 SXSS 5 5 5 5 5
Colour 0.5 0.5 0.5 0.5 0.5
Water OS OS QS OS OS
Notes on Table 9
1 Sodium dodecyl benzene sulphonate
2 Tallowtrimethyl quaternary ammonium chloride 3. 4% DBS/4% quat/3% TAEO/2% methylglycoside (MG) 4.4%DBS/4%quat/2%MG 5. 4% DBS/0% quat/6% MG
The above results indicate that methyl glycoside imparts softening benefits to fabric. The lab tests also indicate that the glycoside imparts brightening benefits in liquid formulations.However, in the absence of quat. no static control is achieved.
The precise composition of Examples 3Ato 3E is set out in Table 9 below.
Table9
PRODUCT 1 2 3 4 5
Example 3B 3C 3D 3A 3E Parts % Ingredients
Neodol 21 21 21 21 21 'DBS' 6 5 4 4 4 quat2 6 5 4 4 TAEO3 - 6 3 -
MG4 - - 2 2 6
Brightener 0.4 0.4 0.4 0.4 0.4
Ethanol 8 8 8 8 8 SXSs 5 5 5 5 5
Colour 0.5 0.5 0.5 0.5 0.5
Water QS QS QS QS QS
Notes on Table 9
1 Sodium dodecyl benzene sulphonate
2Tallowtrimethyl quaternaryammoniumchloride 3 Tallow amine 15 ethylene oxide
4 Methyl glycoside
5 Sodium xylene sulphonate
The detergents (or softergent) containing an alkyl glycoside have been unexpectedly found to not only overcome the reduction in detergency due to the presence of the quaternary softening agent, but have improved the detergency and the softening properties of the detergent (of softergent) compositions.This is clearly shown in Table 8 by Product 4 (Example 3A) containing only 2% methyl glycoside, exhibiting a greater degree of softness (6.8) than Products 1 (Example 3B) (5.9), 2 (Example 3C) (5.8) and 3 (Example 3D) (6.0).
Likewise, Product4 (Example 3A) exhibits a greater brightness afterthe 1 st, 3rd and 5th wash cycle,than
Products 1,2 and 3, as well as an increased SRI value compared to the products containing no alkyl glycoside.
Amounts as low as 2% alkyl glycoside are effective in improving both the detergency and softening properties of a softergent composition used in the laundering of fabrics. In addition, the formulations ofthe present invention exhibit better cleaning and softening efficacy than other surfactant and/or softener combinations presently on the market, as shown by the comparative results in Tables 2,3,5 and 8Ato 8C.
It isto be understood thattheforegoing detailed description is given merely by way of illustration and that variations may be made therein without departing from the spirit of the invention. The "Abstract" given above is merelyforthe convenience of technical searchers and is not to be given any weight with respectto the scope ofthe invention.
Claims (19)
1. A liquid detergent composition for simultaneously cleaning and softening fabrics comprising four essential ingredients, an effective amount of an alkyl glycoside to improve detergency efficacy and softening properties in the presence of a quaternary ammonium softening compound, an anioniosurfactantand a nonionic su rfactant in an aqueous carrier.
2. A composition as claimed in Claim 1 in which the amount of alkyl glycoside is sufficient to overcome the decrease in detergency efficacy due to the presence of the quaternary ammonium content, and constitutes about 2 to 55% by weight of the composition.
3. A composition as claimed in Claim 1 or Claim 2 in which the alkyl glycoside has one or more hydrophobic groups containing 1 to 30 carbon atoms per hydrophobic group, and a hydrophilic glycoside group containing 1 to 10 reducing saccharide radicals.
4. A composition as claimed in Claim 1,2 or 3 in which the alkyl glycoside is a C1-C30 alkyl monoglycoside or polyglycoside.
5. A composition as claimed in Claim 4 in which the alkyl glycoside is C12-C13 alkyl glycoside.
6. A composition as claimed in Claim 4, in which the glycoside is methyl monog lycoside.
7. A composition as claimed in Claim 4 in which the glycoside is C12-C13 alkyl triglycoside.
8. Acomposition as claimed in any one of Claims 1 to7 in which inthequaternaryammonium compound at least one ofthe four groups linked to the nitrogen atom is a C10- C20 alkyl group and at leasttwo ofthe groups are C1- C3alkyl groups andthefourth group may be eitheranotherCaO- C20alkyl group ora C1- C3 alkyl group.
9. A composition as claimed in any one of Claims 1 to 8 in which the quaternary compound constitutes about2 to 8% by weight of the composition.
10. A composition as claimed in any one of Claims 1 to 9 in which the non ionic surfactant is selected from the group consisting of primary aliphatic alcohol ethoxylates, secondary aliphatic alcohol ethoxylates, alkylphenol ethoxylates, alcohol ethylene oxidepropylene oxide condensates, and mixtures thereof.
11. Acomposition as claimed in any one ofthe preceding claims in which the nonionicsurfactant constitutes about 8 - 25% by weight of the composition.
12. Acomposition as claimed in Claim 10 or Claim 11 in which the total nonionicsurfactantcontent consisting ofthe combination ofthe alcohol ethoxylateand the alkyl glycoside constitutes the major detergent component in an amount of about 25- 40% by weight of the composition.
13. A composition as claimed in Claim 10,11 or 12 in which the nonionicsurfactant is a C12-C15aliphatic alcohol having 7 ethylene-oxy groups per mole of alcohol.
14. A composition as claimed in any one of the preceding claims in which the anionic surfactant is selected from the group consisting of alkyibenzene sulphonates, alcohol ether sulphates, olefin sulphonates, paraffin sulphonates, alkyl sulphates, and ethoxylated alcohol sulphates.
15. A composition as claimed in any one of the preceding claims in which the anionic surfactant content is lessthan the nonionic surfactant content and constitutes about 1 - 12% by weight of the composition.
16. Acomposition as claimed in Claim 14 or Claim 15 in which the anionic surfactant is the sodium salt of the ethoxylated C12- C15 alcohol sulphate containing 3 moles ethylene oxide per mole alcohol.
17. Acomposition as claimed in anyoneofthe preceding claims in which the anionicsurfactant is sodium dodecyl benzenesulphonate.
18. A composition as claimed in Claim 1 substantially as specifically described herein with reference to the accompanying Examples.
19. A method of simultaneously cleansing and softening fabrics without reducing brightener and detergency performance which comprises treating fabrics with a composition as claimed in any one ofthe preceding claims in the wash cycle of the laundering operation.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82392686A | 1986-01-30 | 1986-01-30 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB8701854D0 GB8701854D0 (en) | 1987-03-04 |
| GB2185992A true GB2185992A (en) | 1987-08-05 |
| GB2185992B GB2185992B (en) | 1990-09-26 |
Family
ID=25240144
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8701854A Expired - Lifetime GB2185992B (en) | 1986-01-30 | 1987-01-28 | Liquid softergent having improved detergency containing alkyl glycoside |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPH07113119B2 (en) |
| KR (1) | KR950003426B1 (en) |
| AR (1) | AR247588A1 (en) |
| AT (1) | AT397809B (en) |
| AU (1) | AU595851B2 (en) |
| BE (1) | BE1002958A4 (en) |
| BR (1) | BR8700392A (en) |
| CH (1) | CH671963A5 (en) |
| DE (1) | DE3702287A1 (en) |
| DK (1) | DK167881B1 (en) |
| EG (1) | EG18097A (en) |
| ES (1) | ES2004081A6 (en) |
| FR (1) | FR2593516B1 (en) |
| GB (1) | GB2185992B (en) |
| GR (1) | GR870125B (en) |
| HK (1) | HK97693A (en) |
| IL (1) | IL81353A (en) |
| IN (1) | IN170107B (en) |
| IT (1) | IT1205726B (en) |
| MX (1) | MX168268B (en) |
| NL (1) | NL8700231A (en) |
| NO (1) | NO169661C (en) |
| NZ (1) | NZ219051A (en) |
| PH (1) | PH25243A (en) |
| SE (1) | SE8700324L (en) |
| TR (1) | TR24572A (en) |
| ZA (1) | ZA87561B (en) |
| ZW (1) | ZW1887A1 (en) |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4844824A (en) * | 1988-02-08 | 1989-07-04 | The Procter & Gamble Company | Stable heavy duty liquid detergent compositions which contain a softener and antistatic agent |
| EP0315126A3 (en) * | 1987-11-05 | 1990-03-21 | Colgate-Palmolive Company | Liquid softergent formulations having improved stability and softening properties |
| EP0379398A3 (en) * | 1989-01-19 | 1990-09-12 | Colgate-Palmolive Company | Softergent with sugar ethers as detergency boosters |
| FR2666346A1 (en) * | 1990-09-05 | 1992-03-06 | Oreal | COSMETIC WASHING AND / OR TREATING COMPOSITION WITH FAST DRYING KERATIN FIBER BASED ON FLUORINATED CATIONIC COMPOUNDS AND ALKYLPOLYGLYCOSIDES. |
| EP0353735A3 (en) * | 1988-08-04 | 1992-03-18 | Kao Corporation | Detergent composition |
| US5230835A (en) * | 1988-08-04 | 1993-07-27 | Kao Corporation | Mild non-irritating alkyl glycoside based detergent compositions |
| WO1995013347A1 (en) * | 1993-11-08 | 1995-05-18 | Henkel Kommanditgesellschaft Auf Aktien | Fabric-softening detergent with alkyl glycosides |
| WO1996015213A1 (en) * | 1994-11-14 | 1996-05-23 | Henkel Kommanditgesellschaft Auf Aktien | Textile softening agents |
| WO1997012019A1 (en) * | 1995-09-29 | 1997-04-03 | The Procter & Gamble Company | Stable, aqueous laundry detergent composition having improved suspension properties |
| US5627144A (en) * | 1992-09-11 | 1997-05-06 | Henkel Kommanditgesellschaft Auf Aktien | Composition for enhanced crude oil recovery operations containing hydrochloric acid or hydrofluoric acid, or mixtures thereof with ester quaternary ammonium compounds or/and alkyl quaternary ammonium compounds |
| WO1998003717A1 (en) * | 1996-07-23 | 1998-01-29 | Henkel Kommanditgesellschaft Auf Aktien | Process for providing fibres or nonwovens with a hydrophilic coating |
| EP0849354A1 (en) | 1996-12-20 | 1998-06-24 | Unilever Plc | Softening compositions |
| GB2340843A (en) * | 1998-08-25 | 2000-03-01 | Reckitt & Colman Inc | Liquid laundry detergent compositions |
| US6235703B1 (en) | 1996-04-02 | 2001-05-22 | Lever Brothers, Division Of Conopco, Inc. | Surfactant blends, processes for preparing them and particulate detergent compositions containing them |
| EP0757714B1 (en) * | 1994-04-25 | 2001-07-04 | The Procter & Gamble Company | Stable, aqueous laundry detergent composition having improved softening properties |
| US6384010B1 (en) | 2000-06-15 | 2002-05-07 | S.C. Johnson & Son, Inc. | All purpose cleaner with low organic solvent content |
| WO2002102951A1 (en) * | 2001-06-19 | 2002-12-27 | Ciba Specialty Chemicals Water Treatments Limited | Particles containing fabric conditioner |
| US6930082B2 (en) | 2001-03-15 | 2005-08-16 | Unilever Home & Personal Care Usa Division Of Conopco, Inc. | Fabric softening compositions |
| WO2023170120A1 (en) * | 2022-03-10 | 2023-09-14 | Unilever Ip Holdings B.V. | Concentrated fabric conditioner |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL81354A (en) * | 1986-01-30 | 1990-11-05 | Colgate Palmolive Co | Liquid detergent having improved softening properties |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS598392B2 (en) * | 1979-06-29 | 1984-02-24 | 花王株式会社 | cleaning composition |
| JPS58132094A (en) * | 1981-09-28 | 1983-08-06 | ザ、プロクタ−、エンド、ギヤンブル、カンパニ− | Detergent composition |
| GR76286B (en) * | 1981-09-28 | 1984-08-04 | Procter & Gamble | |
| ATE21926T1 (en) * | 1982-05-10 | 1986-09-15 | Procter & Gamble | LOW-PHOSPHATE LAUNDRY DETERGENT COMPOSITIONS. |
| JPS59145299A (en) * | 1982-10-18 | 1984-08-20 | ザ,プロクタ−,エンド,ギヤンブル,カンパニ− | Polyethylene glycol containing liquid detergent |
| IL81354A (en) * | 1986-01-30 | 1990-11-05 | Colgate Palmolive Co | Liquid detergent having improved softening properties |
-
1987
- 1987-01-22 IL IL81353A patent/IL81353A/en unknown
- 1987-01-23 NZ NZ219051A patent/NZ219051A/en unknown
- 1987-01-26 ZA ZA87561A patent/ZA87561B/en unknown
- 1987-01-27 GR GR870125A patent/GR870125B/en unknown
- 1987-01-27 ZW ZW18/87A patent/ZW1887A1/en unknown
- 1987-01-27 PH PH34768A patent/PH25243A/en unknown
- 1987-01-27 IN IN53/DEL/87A patent/IN170107B/en unknown
- 1987-01-27 DE DE19873702287 patent/DE3702287A1/en not_active Withdrawn
- 1987-01-28 SE SE8700324A patent/SE8700324L/en not_active Application Discontinuation
- 1987-01-28 IT IT47579/87A patent/IT1205726B/en active
- 1987-01-28 AU AU68053/87A patent/AU595851B2/en not_active Ceased
- 1987-01-28 EG EG52/87A patent/EG18097A/en active
- 1987-01-28 GB GB8701854A patent/GB2185992B/en not_active Expired - Lifetime
- 1987-01-29 NO NO870367A patent/NO169661C/en unknown
- 1987-01-29 ES ES878700215A patent/ES2004081A6/en not_active Expired
- 1987-01-29 FR FR878701079A patent/FR2593516B1/en not_active Expired - Lifetime
- 1987-01-29 BR BR8700392A patent/BR8700392A/en active Search and Examination
- 1987-01-29 AT AT0017687A patent/AT397809B/en not_active IP Right Cessation
- 1987-01-30 DK DK051387A patent/DK167881B1/en active
- 1987-01-30 CH CH342/87A patent/CH671963A5/de not_active IP Right Cessation
- 1987-01-30 AR AR87306640A patent/AR247588A1/en active
- 1987-01-30 MX MX005112A patent/MX168268B/en unknown
- 1987-01-30 JP JP62020366A patent/JPH07113119B2/en not_active Expired - Lifetime
- 1987-01-30 KR KR1019870000745A patent/KR950003426B1/en not_active Expired - Lifetime
- 1987-01-30 BE BE8700064A patent/BE1002958A4/en not_active IP Right Cessation
- 1987-01-30 NL NL8700231A patent/NL8700231A/en not_active Application Discontinuation
- 1987-01-30 TR TR87/0077A patent/TR24572A/en unknown
-
1993
- 1993-09-23 HK HK976/93A patent/HK97693A/en unknown
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0315126A3 (en) * | 1987-11-05 | 1990-03-21 | Colgate-Palmolive Company | Liquid softergent formulations having improved stability and softening properties |
| AU619502B2 (en) * | 1987-11-05 | 1992-01-30 | Colgate-Palmolive Company, The | Liquid softergent formulations having improved stability and softening properties |
| US4844824A (en) * | 1988-02-08 | 1989-07-04 | The Procter & Gamble Company | Stable heavy duty liquid detergent compositions which contain a softener and antistatic agent |
| EP0353735A3 (en) * | 1988-08-04 | 1992-03-18 | Kao Corporation | Detergent composition |
| US5230835A (en) * | 1988-08-04 | 1993-07-27 | Kao Corporation | Mild non-irritating alkyl glycoside based detergent compositions |
| EP0379398A3 (en) * | 1989-01-19 | 1990-09-12 | Colgate-Palmolive Company | Softergent with sugar ethers as detergency boosters |
| FR2666346A1 (en) * | 1990-09-05 | 1992-03-06 | Oreal | COSMETIC WASHING AND / OR TREATING COMPOSITION WITH FAST DRYING KERATIN FIBER BASED ON FLUORINATED CATIONIC COMPOUNDS AND ALKYLPOLYGLYCOSIDES. |
| EP0477057A1 (en) * | 1990-09-05 | 1992-03-25 | L'oreal | Washing composition and/or cosmetic composition for rinsing keratin fibres, for quick drying based on cationic fluorinated compounds and alkylpolyglycosides, and the processes for using these compositions |
| US5627144A (en) * | 1992-09-11 | 1997-05-06 | Henkel Kommanditgesellschaft Auf Aktien | Composition for enhanced crude oil recovery operations containing hydrochloric acid or hydrofluoric acid, or mixtures thereof with ester quaternary ammonium compounds or/and alkyl quaternary ammonium compounds |
| WO1995013347A1 (en) * | 1993-11-08 | 1995-05-18 | Henkel Kommanditgesellschaft Auf Aktien | Fabric-softening detergent with alkyl glycosides |
| EP0757714B1 (en) * | 1994-04-25 | 2001-07-04 | The Procter & Gamble Company | Stable, aqueous laundry detergent composition having improved softening properties |
| WO1996015213A1 (en) * | 1994-11-14 | 1996-05-23 | Henkel Kommanditgesellschaft Auf Aktien | Textile softening agents |
| WO1997012019A1 (en) * | 1995-09-29 | 1997-04-03 | The Procter & Gamble Company | Stable, aqueous laundry detergent composition having improved suspension properties |
| US6235703B1 (en) | 1996-04-02 | 2001-05-22 | Lever Brothers, Division Of Conopco, Inc. | Surfactant blends, processes for preparing them and particulate detergent compositions containing them |
| US6177367B1 (en) | 1996-07-23 | 2001-01-23 | Henkel Kommanditgesellschaft Auf Aktien | Process for providing fibers or nonwovens with a hydrophilic coating |
| WO1998003717A1 (en) * | 1996-07-23 | 1998-01-29 | Henkel Kommanditgesellschaft Auf Aktien | Process for providing fibres or nonwovens with a hydrophilic coating |
| EP0849354A1 (en) | 1996-12-20 | 1998-06-24 | Unilever Plc | Softening compositions |
| GB2340843A (en) * | 1998-08-25 | 2000-03-01 | Reckitt & Colman Inc | Liquid laundry detergent compositions |
| US6384010B1 (en) | 2000-06-15 | 2002-05-07 | S.C. Johnson & Son, Inc. | All purpose cleaner with low organic solvent content |
| US6930082B2 (en) | 2001-03-15 | 2005-08-16 | Unilever Home & Personal Care Usa Division Of Conopco, Inc. | Fabric softening compositions |
| WO2002102951A1 (en) * | 2001-06-19 | 2002-12-27 | Ciba Specialty Chemicals Water Treatments Limited | Particles containing fabric conditioner |
| WO2023170120A1 (en) * | 2022-03-10 | 2023-09-14 | Unilever Ip Holdings B.V. | Concentrated fabric conditioner |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19940128 |