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WO1992006171A1 - Compositions detergentes liquides - Google Patents

Compositions detergentes liquides Download PDF

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Publication number
WO1992006171A1
WO1992006171A1 PCT/US1991/006977 US9106977W WO9206171A1 WO 1992006171 A1 WO1992006171 A1 WO 1992006171A1 US 9106977 W US9106977 W US 9106977W WO 9206171 A1 WO9206171 A1 WO 9206171A1
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WO
WIPO (PCT)
Prior art keywords
alkyl
weight
mixture
composition according
gel
Prior art date
Application number
PCT/US1991/006977
Other languages
English (en)
Inventor
Julie Anne Dyet
Peter Robert Foley
Original Assignee
The Procter & Gamble Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=10682966&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO1992006171(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority to DE69113055T priority Critical patent/DE69113055T2/de
Priority to KR1019930700912A priority patent/KR100221444B1/ko
Priority to AU87352/91A priority patent/AU664023B2/en
Priority to JP3517000A priority patent/JP3007150B2/ja
Priority to BR919106935A priority patent/BR9106935A/pt
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to SK25393A priority patent/SK25393A3/sk
Priority to EP91918093A priority patent/EP0550636B1/fr
Publication of WO1992006171A1 publication Critical patent/WO1992006171A1/fr
Priority to NO93931078A priority patent/NO931078L/no
Priority to FI931369A priority patent/FI931369A7/fi
Priority to GR950402408T priority patent/GR3017416T3/el

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0008—Detergent materials or soaps characterised by their shape or physical properties aqueous liquid non soap compositions
    • C11D17/003—Colloidal solutions, e.g. gels; Thixotropic solutions or pastes
    • 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
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/525—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain two or more hydroxy groups per alkyl group, e.g. R3 being a reducing sugar rest
    • 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
    • C11D1/65—Mixtures of anionic with cationic compounds
    • C11D1/652—Mixtures of anionic compounds with carboxylic amides or alkylol amides
    • 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
    • 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
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/32—Amides; Substituted amides
    • 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
    • C11D1/18—Sulfonic acids or sulfuric acid esters; Salts thereof derived from amino alcohols
    • C11D1/20—Fatty acid condensates
    • 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
    • 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
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/523—Carboxylic alkylolamides, or dialkylolamides, or hydroxycarboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain one hydroxy group per alkyl group
    • 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
    • C11D1/75—Amino oxides
    • 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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/90—Betaines
    • 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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/92—Sulfobetaines ; Sulfitobetaines

Definitions

  • This invention relates generally to aqueous liquid detergent compositions and more particularly to liquid detergent compositions intended to remove soils of a largely greasy nature from hard surfaces such as dishes and other articles used in food preparation and
  • Liquid detergent compositions intended for use as dishwashing products conventionally take the form of aqueous solutions containing a mixture of one or more sulphate and sulphonate anionic detergents as 'core' surfactant materials together with a suds promoting or stabilising agent.
  • the suds stabilisation agent can take a number of forms but is normally an amide
  • N-alkanoyl N-alkyl glucamines These materials are derived from glucose and can be prepared by reacting a lower alkylamine with glucose to form a glucamine and then treating this with a methyl ester of a fatty acid of the required chain length to give the N-alkanoyl-N-alkyl glucamine.
  • detergent compositions comprising at least one water soluble salt of an organic sulphuric reaction product having in its molecular structure a sulphuric acid or a sulphonic acid radical and an amide derivative of the above type in an amount of from 5% to 60% by weight of the water soluble organic sulphuric reaction product.
  • the amide derivatives are stated to provide an improvement in the sudsing characteristics of the compositions at temperatures below 100oF particularly in Latin American countries where washing is carried out at temperatures as low as 60°F.
  • embodiments are granular products incorporating phosphate builder and sodium sulphate filler.
  • surfactants combinations of certain N-alkanoyl -N-alkyl glucamines with sulphated or sulphonated surfactants, provide a significant improvement in the removal of greasy soils from hard surfaces together with superior sudsing mileage performance and appreciable skin mildness benefits relative to known products.
  • mixtures of anionic sulphate or sulphonate surfactants and N-alkanoyl -N-alkyl glucamines have been proposed as a means of obtaining improvements in the sudsing of built products at low wash temperatures, the performance aspects of greasy soil removal and skin mildness properties that have how been found for the mixtures have, hitherto, not been recognised. Therefore, according to the present invention, there is provided an unbuilt liquid er gel-form detergent
  • composition in the form of a physically stable aqueous solution comprising from 15% to 65% by weight of the composition of a core surfactant mixture, comprising by weight of the mixture,
  • Z is a polyhydroxy hydrocarboxyl moiety having a linear hydrocarbyl chain with at least three hydroxy groups connected directly to the chain, said moiety being derived from glucose and mixtures thereof with maltose, the maltose comprising not more than 33% by weight of the mixture, R it a saturated or unsaturated aliphatic group of from 8 to 16 carbon atoms or a mixture of such groups and R 1 is a C 1 -C 4 alkyl or C 2 -C 4 hydroxyalkyl group;
  • a 0.12% by weight aqueous solution of the surfactant mixture of said composition in water of 2o Clark mineral hardness (Ca:Mg ratio of 3:1) and temperature of 48oC, has i) a spinning drop iaterfacial tension (lFT) of less than 0.2 Pa cm using a triolein soil of 99.7% purity;
  • the cation(s) of the water soluble anionic sulfate or sulfonate surfactant shall be such as to correspond to the cation (s) in the detergent composition, and where a mixture of cations is present, in the weight proportions in which each cation is present in the mixture.
  • compositions in accordance with the invention employ component b) compounds in which the
  • polyhydroxyhydrocarbyl moieties are derived from glucose or mixtures thereof with maltose in which maltose
  • glucose comprises ⁇ 25% by weight of the mixture.
  • Commercially available technical grade glucose contains maltose as an impurity at a level of up to 5% by weight.
  • references hereinafter to glucamines are to be construed as material including up to 5% by weight of the corresponding material derived from maltose.
  • Suitable anionic sulphate or sulphonate surfactants include C 10 -C 16 alkyl ethoxy sulphates containing an average of up to 6 moles of ethylene oxide per mole of alkyl
  • an anionic surfactant system comprising from 9% to 18% by weight of the composition of a primary
  • composition of N-coconut acyl-N-methyl glucamine employ an anionic surfactant to glucamine weight ratio of between 2:1 and 1:1.
  • compositions contain from 10% to 18% by weight of C 12 -C 14 alkyl ethoxy sulphate and from
  • the alkyl ethoxy sulphates themselves comprise a mixture of material containing an average of approximately 0 moles of ethylene oxide/mole and material containing an average of approximately 3.0 moles of ethylene oxide/mole in a weight ratio of between 2:1 and 5:1 preferably
  • compositions in accordance with the invention also contain l%-8%, most preferably 2%-7% by weight of a suds booster selected from C 10 -C 16 alkyl mono or
  • amido betaines C 12 -C 14 alkyl sulphobetaines
  • ethoxylates containing an average of from 7 to 12 ethylene oxide groups per mole of alcohol and mixtures thereof.
  • Preferred suds boosters comprised mixtures of C 12 -C 14 alkyl betaine, in an amount of from 1% to 5% preferably from 1.5% to 3% by weight of the composition, together with C 9 -c 12 primary alcohol ethoxylate (preferably C 10 alkyl EO 8 ) in an amount of from 6% to 8% by weight of the composition.
  • compositions are Mg ++ , at a level of up to 5% more preferably from 0.5% to 1.0% by weight of the compositions.
  • Especially preferred compositions also contain calcium in a dition to the magnesium ion at a level of from 0.3% to 0.5% by weight.
  • Detergent compositions in accordance with the present invention comprise a mixture of core surfactants in an amount of from 15% to 65% by weight of the composition, preferably from 20% to 50% and more preferably from 22% to 40% by weight.
  • the mixture comprises from 5% to 95% by weight of the mixture of at least one water-soluble anionic sulphate or sulphonate surfactant salt together with from 95% to 5% by weight of the mixture of a N-C 8 -C 16
  • acyl-N-C 1 -C 4 alkyl glucamine nonionic surfactant acyl-N-C 1 -C 4 alkyl glucamine nonionic surfactant.
  • the mixture comprises from 20% to 80% of the anionic surfactant and from 80% to 20% of the alkyl
  • glucamine and most preferably from 40% to 70% anionic surfactant and from 60% to 30% alkyl glucamine.
  • the anionic surfactant can essentially be any organic sulphate or sulphonate surfactant salt but is usually selected from C 11 -C 15 alkyl benzene sulphonates,
  • the anionic surfactant is selected from alkyl ethoxy sulphates, alkyl glyceryl ether sulphonates and paraffin sulphonates.
  • Alkyl benzene sulphonates useful in compositions of the present invention are those in which the alkyl group, which is substantially linear, contains 10-16 carbon atoms, preferably 11-13 carbon atoms, a material with an average carbon chain length of 11.8 being most preferred.
  • the phenyl isomer distribution, i.e. the point of attachment of the alkyl chain to the benzene nucleus, is not critical, but alkyl benzenes having a high 2-phenyl isomer content are preferred.
  • Suitable alkyl sulphates are primary alkyl sulphates in which the alkyl group contains 10-16 carbon atoms, more preferably an average of 12-14 carbon atoms preferably in a linear chain.
  • C 10 -C 16 alcohols, derived from natural fats, or Ziegler olefin build-up, or OXO synthesis, form suitable sources for the alkyl group. Examples of
  • Lutensol by BASF GmbH and Synperonic (RTM) by ICI and Lial 125 sold by Liquichimica Italiana.
  • RTM Synperonic
  • Lial 125 sold by Liquichimica Italiana.
  • Naturally occurring materials from which the alcohols can be derived are coconut oil and palm kernel oil and the corresponding fatty acids.
  • Alkyl ethoxy sulphate surfactants comprise a primary alkyl ethoxy sulphate derived from the condensation product of a C 10 -C 16 alcohol with an average of up to 6 ethylene
  • the C 10 -C 16 alcohol itself can be
  • Blends can be made of material having different degrees of
  • inventions have from 13 to 18 carbon atoms per molecule, more desirably 13 to 15 atoms per molecule.
  • sulphonates are preferably prepared by subjecting a cut of paraffin, corresponding to the chain lengths specified above, to the action of sulphur dioxide and oxygen in accordance with the well-known sulphoxidation process.
  • the product of this reaction is a secondary sulphonic acid which is then neutralized with a suitable base to provide a water-soluble secondary alkyl sulphonate.
  • secondary alkyl sulphonates may be obtained by other methods, e.g. by the sulphochlorination method in which chlorine and sulphur dioxide are reacted with paraffins in the presence of actinic light, the resulting sulphonyl chlorides being hydrolysed and neutralized to form the secondary alkyl sulphonates. Whatever technique is employed, it is normally desirable to produce the
  • the monosulphonate may be terminally
  • any accompanying disulphonate usually produced when an excess of sulphonating agent is present, may have the sulphonate groups distributed over different carbon atoms of the paraffin base, and mixtures of the monosulphonates and disulphonates may be present.
  • Suitable alkyl glyceryl ether sulphonates are those derived from ethers of coconut oil and tallow.
  • sulphate surfactants include the N-C 9 -C 17
  • acyi-N-C 1 -C 4 alkyl glucamine sulphates preferably
  • the counter ion for the anionic surfactant component can be any one of sodium, potassium, magnesium, ammonium or alkanol-ammonium or a mixture thereof.
  • compositions of the invention sodium is the preferred counter ion but potassium is preferred over sodium where it is of importance that the compositions of the invention
  • liquid detergent compositions in accordance with the invention have a chill point less than 8oC preferably less than 5oC, and are at least partially neutralised by ammonium ions. Where calcium and/or magnesium ions are present they can either be introduced as the oxide or hydroxide to
  • dishwashing compositions in accordance with the invention raises the temperature at which inorganic salt crystals form in the compositions on cooling and the amount added in this way should therefore be minimized.
  • mixtures of calcium and magnesium ions may be added in order to provide up to 1% ca ++ by weight of the
  • compositions more preferably from 0.3% to 0.5% Ca ++ and up to 1.50% Mg ++ , more preferable from 0.5% to 1.0% by weight.
  • the preferred mixtures are rich in magnesium and more preferably provide a Ca ++ :Mg ++ weight ratio of from 1:1 to 1:4.
  • Compositions incorporating Mg ++ and/or Ca ++ are especially valuable for conditions of very low water hardness ( ⁇ 2o Clark) and also for product concentrations greater than 0.5% by weight.
  • the second core surfactant component of the unbuilt liquid compositions of the invention is a compound of the general formula
  • Z is a polyhydroxy hydrocarbyl moiety having a linear hydrocarbyl chain with at least three hydroxy groups groups connected directly to the chain, said moiety being derived from glucose and mixtures thereof with maltose, the maltose comprisisg not more than 33% by weight of the mixture, R is a saturated or unsaturated aliphatic group of from 8 to 16 carbon atoms, or a mixture of such groups, and R 1 is a C 1 -C 4 alkyl or C 2 -C 4 hydroxyl alkyl group.
  • R may be derived from any of the sources of hydrocarbyl groups discussed hereinbefore with reference to the anionic surfactant but is preferably natural in origin.
  • R has an average chain length of from 12 to 14 carbon atoms and is derived from coconut oil or palm kernel oil.
  • R 1 is preferably a methyl group.
  • the first step involves reacting glucose and a primary
  • n lie between 8% and 25% by weight, more preferably between 9% and 18% and most preferably between 10% and 15% by weight.
  • compositions in accordance with the invention can be formulated with calcium ions in the
  • N- alkanoyl -N-alkyl glucamines of high purity in which the levels of unreacted starting materials, impurities and by-products, particularly fatty acids, are minimised.
  • the balance of the liquid detergent composition can be made up by water or, in the case of a gel-form composition by a gelling agent and water.
  • a gelling agent in preferred compositions,
  • glucamine components lie in the range from 20% to 40%, more preferably from 22% to 30% by weight.
  • a highly desirable optional component is one or more suds modifiers or promoters, normally present at an individual level of from 1% to 8% by weight of the composition. Certain of these materials also have additional functional value as e.g. soil suspending agents.
  • One such suds promoting agent is a C 10 -C 16 alkyl mono- or
  • the palm kernel or coconut alkyl residue may either be 'whole cut', including the C 10 and C 16 fractions or may be the so-called 'narrow-cut' C 12 -C 14 fraction '
  • Synthetic sources of the C 10 -C 16 alkyl group can also be used.
  • Another useful suds promoting agent is a zwitterionic surfactant of general formula
  • R 1 is C 10 -C 16 alkyl
  • R 2 is C 1 -C 3 alkyl
  • R 3 is a -(CH 2 ) 3 group or a -(CH 2 - - CH 2 ) group
  • Y is - - - (CH 2 ) 3 -
  • n & m are 0 or 1
  • X- is CH 2 COO- or SO 3 ;
  • X- is SO 3 , n is O and m is 1.
  • R 1 has an average carbon chain length of from 12 to 16 carbon atoms and may be derived from
  • a further class of suds promoting agents useful in the invention are the amine oxides of general formula
  • R 1 R 2 R 3 N------- ⁇ O wherein R 1 is an alkyl group
  • R 2 and R 3 are each independently selecte ⁇ from C 1 -C 3 alkyl and
  • Preferred members of this class include dimethyldodecyl amine oxide, dimethyl tetradecyl amine oxide, bis-(2 hydroxyethyl) dodecylamine oxide and analogues thereof in which the dodecyl or
  • tetradecyl moiety is derived from natural sources such as coconut or palm kernel oil.
  • a preferred suds modifyir agent is an ethoxylated alcohol or a mixture of ethoxylate. alcohols of defined
  • the ethoxylated alcohol comprises a C 6 -C 13 aliphatic alcohol ethoxylate containing an average of from 1.5 to 25, more preferably from 2 to 15 and most preferably from 6 to 10 moles of ethylene oxide per mole of alcohol.
  • the aliphatic alcohol ethoxylate contains not more than 1% by weight of unethoxylated alcohol where the ethoxylated alcohol contains an average of less than 8 moles of
  • the starting alcohol may be a primary or secondary alcohc but is preferably a primary alcohol which may be derived from natural or synthe ic sources.
  • natural fats or oils, or products of Ziegler olefin build up reactions or OXO synthesis may all be used as the source of the
  • hydrocarbon chain the structure of which may be linear or branched in type.
  • the preferred alcohol chain length range is from C 9 to C 11 as it has been found that the sudsing volume and mileage performance of compositions in accordance with the invention is optimum when incorporating ethoxylates made from such alcohols.
  • HLB hydrophilic-lipophilic balance
  • a preferred alcohol ethoxylate is a
  • ethoxylate species which ranges from 1 to 15 moles of ethylene oxide per mole of alcohol.
  • An increase in E av causes some change in this distribution, principally a reduction in the level of unethoxylated material, but an increase in E av from 3 to 5 will still leave
  • this level of unethoxylated material will give rise to phase stability/chill point problems and/or will result in a product having a fatty alcohol odour which is unacceptable to consumers and cannot be masked by
  • the maximum level of unethoxylated alcohol that can be tolerated in the ethoxylated alcohol component is 1% by weight. More preferably the unethoxylated alcohol level is not more than 0.7% and most preferably is less than 0.5% by weight of the ethoxylated alcohol component. Distillation under vacuum is employed to remove the
  • the level of monoethoxylate is not more than 5% by weight of the ethoxylated alcohol.
  • compositions in accordance with the invention are used, each being present at a level of from 1% to 10% more preferably from 2% to 8% by weight.
  • One such preferred combination is a C 12 -C 14 alkyl dimethyl betaine and a
  • the balance of the formula comprises a hydrotrope-water system in which the hydrotrope may be urea, a C 1 -C 3 aliphatic alcohol, a lower alkyl or dialkyl benzene sulphonate salt such as toluene
  • compositions in accordance with the present invention preferably employ a mixture such as urea-alcohol-water, alcohol-lower alkyl benzene sulphonate-water or urea-lower alkyl benzene sulphonate-water in order to achieve the desired viscosity, and to remain stable and easily
  • the preferred alcoholic hydrotrope is ethanol which is employed at from 3% to 10% by weight of the composition, preferably at from 4% to 8%, usually in admixture with urea.
  • compositions having an organic active concentration greater than about 40% by weight mixtures of ethanol with urea and/or lower alkyl benzene sulphonates are preferred.
  • Optional ingredients of the liquid detergent compositions of the invention include opacifiers such as ethylene glycol distearate, thickeners such as guar gum, antibacterial agents such as glutaraldehyde and Bronopol (RTM),
  • opacifiers such as ethylene glycol distearate
  • thickeners such as guar gum
  • antibacterial agents such as glutaraldehyde and Bronopol (RTM)
  • the pH of the compositions may be anywhere within the range 6.0-8.5,but as manufactured the compositions normally have a pH in the range 6.5-7.3 and are subjected to a final pH trimming operation to obtain the desired finished product pH.
  • the pH preferably lies in the range 6.5-7.2 in order to maintain colour stability.
  • compositions of the invention can be made in a number of ways but it is preferred that any zwitterionic
  • surfactant included therein is incorporated towards the end of the making process if not actually forming the last ingredient to be added. This minimises the risk of any degradation of the zwitterionic surfactant under the acid conditions existing at the beginning of the making process and also facilitates the control of the viscosity of the finished product.
  • the glucamine surfactant should not be exposed to a pH lower than 4 or higher than 10 to prevent hydrolysis of the surfactant.
  • anionic surfactant(s) can be made as aqueous sections of alkali metal or ammonium salts with pH
  • chill point temperature the temperature at which inorganic salts precipitate as crystals in the liquid.
  • compositions containing an alkyl ethoxy sulphate as the anionic surfactant the desired alcohol and alcohol ethoxylate 'in be mixed together and a single sulphation and netu alisation can then be carried out on these two materials.
  • the alcohol and alcohol ethoxylate should be mixed in a weight ratio lying in the range from 4:3 to 1:6. in the most preferred technique however, a single alcohol ethoxylate stock is produced in which the levels of alcohol and ethoxylated alcohol species are controlled to provide the desired ratio of these
  • Sulph(on)ation of the alcohol and alcohol ethoxylate can employ any of the conventional sulph(on)ating agents such as sulphur trioxide or chlorosulphonic acid.
  • magnesium/calcium oxide or hydroxide slurry If the
  • anionic surfactant is not sufficient to permit all of the desired Ca ++ and Mg ++ ions to be added in this way, the remainder can then be added in the form of a
  • Gel compositions of the present invention can be prepared using the general method described in US Patent No. 4615819.
  • compositions in accordance with the invention are:
  • IFT interfacial tension
  • PPC polypropylene cup
  • compositions in accordance with the invention display superior suds mileage performance in both hard and soft water, by comparison with prior art compositions.
  • IFT IFT Measurement of IFT gives an indication of the ability of a surfactant sample to emulsify a soil under a defined set of conditions. IFT was determined by means of a Spinning Drop Tensiometer and a University of Texas Model 500 manufactured by the University of Texas,
  • the soil was Triolein of 99.7% purity (the remaining 0.3% comprising mixed free fatty acids) supplied by ALDRICH Chemical Company Ltd. New Road,
  • the Polypropylene Cup Test method measures the overall grease handling capability of a product under conditions sinflating those found in manual dishwashing practice.
  • the test involves the measurement of the amount of solid fat removal from the base of a polypropylene cup at a temperature below that at which the fat melts.
  • a fat soil is prepared by making a mixture of the following fats:
  • the cups are held level and the fat allowed to solidify for 2-3 hours in a constant temperature room at 21 ⁇ 1oC.
  • test product A 0.12% solution of the test product is prepared at 50-55°C and 100 ⁇ 0.1g added to each of five glass jars which are
  • Products in accordance with the invention display a
  • the standard product should have a grease handling performance in the same general area as that of the experimental product at the same
  • Total suds is the total volume of suds generated during a standard dishwashing test and is a measure of the perceived foaming ability of the formulation. Suds
  • the method uses 4 cylinders of length 30 cm and diameter 10 cm fixed side by side, and rotatable at a speed of 24 rpm about a central axis. Each cylinder is charged with 500 mis of product solution at a concentration of 0.12% and a temperature of 48°C. The outer two cylinders are used for one of the products being compared and the inner two for the other product.
  • the cylinders are rotated for 2 minutes, stopped, the initial suds are measured and a soil load is then added typically in 2ml aliquots. After 1 minute the cylinders are restarted and allowed to rotate for 1 minute. The suds height is noted and 2 mis of the soil is added to each cylinder. After 1 minute the cylinders are restarted. This process continues until the suds height in the
  • cylinder is lower than 0.6 cms.
  • the total of all of the suds height measurements in each test (i.e. until the suds height becomes lower than 0.6 cms) forms the Total Suds measurement.
  • a range of core surfactant systems was prepared containing a mixture of alkyl ethoxysulphate surfactant and
  • the alkyl ethoxysulphate was derived from a C 12 -C 14 primary alcohol condensed with an average of 0.8 moles of ethylene oxide per mole of alcohol and neutralised with a mixture of ammonium and magnesium ions so as to contain 0.22 moles of magnesium per mole of alkyl ethoxysulphate.
  • a simulated product of 30% core surfactant concentration was first made in distilled water. A 0.12% by weight solution of this product was then formed in either soft (2° Clark) or hard (18° Clark) water and tested for IFT, and in 2° Clark water for PPC greasy soil removal, using the test methods hereinbefore described. This procedure was followed for ratios of alkyl ethoxy sulphate to alkyl glucamine of 100:0, 75:25, 65:35, 50:50, 25:75 and 0:100 and the results are shown below.
  • compositions A - E were prepared:
  • Composition A represents a comparative commercially available liquid detergent dishwashing product while Compositions B, C, D & E are in accordance with the invention.

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Abstract

Compositions détergentes aqueuses non structurées sous forme liquide ou de gel, comprenant de 15 % à 65 % en poids d'un poids d'un mélange noyau tensioactif, comprenant de 5 % à 95 % en poids du mélange d'un sulfate anionique soluble ou d'un sel de sulfonate tensioactif et entre 5 % et 95 % en poids du mélange d'un ou plusieurs composés de formule (I), dans laquelle Z est une fraction de polyhydroxy hydrocarbyle possédant une chaîne hydrocarbyle linéaire présentant au moins trois groupes hydroxy reliés directement à la chaîne, ladite fraction étant dérivée du glucose et de ses mélanges avec du maltose, le maltose ne représentant pas plus de 33 % du mélange, R est un radical hydrocarbyle C6-C16 et R1 est un groupe alkyle C1-C4 ou un groupe hydroxyalkyle C2-C4, une solution à 0,12 % des mélanges tensioactifs des compositions présentant une tension interfaciale (IFT) inférieure à 0,2 Pa.cm à 48 °C et une valeur d'élimination de taches de graisse obtenue par test PPC égale à au moins 1,4 fois celle du/des composant(s) tensioactif(s) anionique(s) seul(s). Des ingrédients éventuels préférés comprennent un amide, de la bétaine et des modificateurs de lessives à base d'alcools gras C9-C11 éthoxylés.
PCT/US1991/006977 1990-09-28 1991-09-25 Compositions detergentes liquides WO1992006171A1 (fr)

Priority Applications (10)

Application Number Priority Date Filing Date Title
EP91918093A EP0550636B1 (fr) 1990-09-28 1991-09-25 Compositions detergentes liquides
KR1019930700912A KR100221444B1 (ko) 1990-09-28 1991-09-25 액체 세정제 조성물
AU87352/91A AU664023B2 (en) 1990-09-28 1991-09-25 Liquid detergent compositions
JP3517000A JP3007150B2 (ja) 1990-09-28 1991-09-25 液体洗剤組成物
BR919106935A BR9106935A (pt) 1990-09-28 1991-09-25 Composicoes detergentes liquidas
DE69113055T DE69113055T2 (de) 1990-09-28 1991-09-25 Flüssige waschmittelzusammensetzungen.
SK25393A SK25393A3 (en) 1990-09-28 1991-09-25 Liquid detergent compositions
NO93931078A NO931078L (no) 1990-09-28 1993-03-24 Flytende detergentblandinger
FI931369A FI931369A7 (fi) 1990-09-28 1993-03-26 Flytande detergentkompositioner
GR950402408T GR3017416T3 (en) 1990-09-28 1995-09-14 Liquid detergent compositions.

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GB909021217A GB9021217D0 (en) 1990-09-28 1990-09-28 Liquid detergent compositions
GB9021217.6 1990-09-28

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WO1993005132A1 (fr) * 1991-09-06 1993-03-18 The Procter & Gamble Company Compositions detergentes contenant du calcium et un amide d'acide gras polyhydroxy
EP0572723A1 (fr) * 1992-06-02 1993-12-08 The Procter & Gamble Company Compositions détergentes liquides structurées
US5269974A (en) * 1992-09-01 1993-12-14 The Procter & Gamble Company Liquid or gel dishwashing detergent composition containing alkyl amphocarboxylic acid and magnesium or calcium ions
WO1994005755A1 (fr) * 1992-09-01 1994-03-17 The Procter & Gamble Company Liquide ou gel detergent pour la vaisselle contenant un amide d'acide gras polyhydroxy, des ions de calcium et un alkylpolyethoxypolycarboxylate
WO1994005758A1 (fr) * 1992-09-01 1994-03-17 The Procter & Gamble Company Compositions detergentes liquides ou en gel contenant du calcium et stabilisant de celles-ci
WO1994010273A1 (fr) * 1992-11-04 1994-05-11 The Procter & Gamble Company Gels detersifs
WO1994012598A1 (fr) * 1992-11-30 1994-06-09 The Procter & Gamble Company Compositions nettoyantes comprenant des tensioactifs non ioniques/anioniques d'amides d'acide gras polyhydroxy melanges, a faible pouvoir moussant
WO1994014947A1 (fr) * 1992-12-28 1994-07-07 The Procter & Gamble Company Gels detergents clairs
WO1995006103A1 (fr) * 1993-08-27 1995-03-02 The Procter & Gamble Company Procede de preparation de melanges de tensioactifs concentres contenant du magnesium
WO1995006107A1 (fr) * 1993-08-27 1995-03-02 The Procter & Gamble Company Compositions detergentes concentrees, se presentant sous forme de liquide ou de gel, et contenant du sucre pour lavages delicats tels que le lavage de la vaisselle
WO1995006108A1 (fr) * 1993-08-27 1995-03-02 The Procter & Gamble Company Composition detergente concentree pour le lavage de la vaisselle , se presentant sous forme de liquide ou de gel, et contenant du sulfonate de xylene de calcium
WO1995006106A1 (fr) * 1993-08-27 1995-03-02 The Procter & Gamble Company Compositions detergentes concentrees utilisees pour le lavage de la vaisselle, sous forme de liquide ou de gel, contenant des ions calcium et des tensioactifs de disulfonate
WO1995007330A1 (fr) * 1993-09-09 1995-03-16 The Procter & Gamble Company Detergent de lave-vaisselle automatique contenant un tensioactif d'amide alcoxy ou aryloxy
WO1995007337A1 (fr) * 1993-09-09 1995-03-16 The Procter & Gamble Company Detergent extremement savonnant comprenant un amide d'acide gras n-alkoxy polyhydroxy et des tensioactifs de carboxylate secondaire
WO1995007971A1 (fr) * 1993-09-14 1995-03-23 The Procter & Gamble Company Detergents doux additionnes de protease, sous forme liquide ou de gel
DE4400632C1 (de) * 1994-01-12 1995-03-23 Henkel Kgaa Tensidgemische und diese enthaltende Mittel
EP0656046A1 (fr) * 1992-08-21 1995-06-07 The Procter & Gamble Company Composition concentree de detergent liquide comprenant un sulfate d'ether d'alkyle et son procede de preparation
WO1995030730A1 (fr) * 1994-05-06 1995-11-16 The Procter & Gamble Company Detergent liquide contenant un amide polyhydroxyle d'acide gras et un sel toluene sulfonate
WO1996001306A1 (fr) * 1994-07-05 1996-01-18 The Procter & Gamble Company Composition detergente pour le lavage de linge a la main possedant une douceur et des qualites de nettoyage ameliorees
US5500150A (en) * 1993-09-09 1996-03-19 The Procter & Gamble Company Solidified detergent additive with n-alkoxy polyhydroxy fatty acid amide and alkoxylated surfactant
US5500155A (en) * 1994-03-18 1996-03-19 Henkel Kommanditgesellschaft Auf Aktien Detergent mixtures of fatty acid isethionate salts and fatty alcohols
US5512699A (en) * 1994-01-25 1996-04-30 The Procter & Gamble Company Poly polyhydroxy fatty acid amides
US5534197A (en) * 1994-01-25 1996-07-09 The Procter & Gamble Company Gemini polyhydroxy fatty acid amides
US5580849A (en) * 1992-09-01 1996-12-03 The Procter & Gamble Company Liquid or gel detergent compositions containing calcium and stabilizing agent thereof
USH1632H (en) * 1994-08-15 1997-02-04 Shell Oil Company Liquid laundry detergent formulations
US5607910A (en) * 1993-06-30 1997-03-04 Sherry; Alan E. Detergent gels containing ethoxylated alkyl sulfates and secondary sulfonates
EP0776653A1 (fr) 1995-11-30 1997-06-04 Henkel Kommanditgesellschaft auf Aktien Compositions cosmétiques et/ou pharmaceutiques contenant des amides d'acides gras polyhydroxyle
EP0780464A2 (fr) 1995-12-21 1997-06-25 Henkel Kommanditgesellschaft auf Aktien Procédé pour la préparation des concentrés d'agents tensio-actifs de couleur claire à basse viscosité
US5669984A (en) * 1994-01-25 1997-09-23 The Procter & Gamble Company Method for hand washing dishes containing polyhydroxy amines
WO1997038071A1 (fr) * 1996-04-08 1997-10-16 Colgate-Palmolive Company Compositions liquides detergentes pour lavages delicats
US5686603A (en) * 1995-05-04 1997-11-11 Lever Brothers Company, Division Of Conopco, Inc. Sulfated polyhydroxy compounds as anionic surfactants and a process for their manufacture
US5691300A (en) * 1993-07-12 1997-11-25 Henkel Kommanditgesellschaft Auf Aktien Rinse aids for the machine washing of hard surfaces
US5698505A (en) * 1994-01-25 1997-12-16 The Procter & Gamble Company High sudsing light duty liquid or gel dishwashing detergent compositions containing long chain amine oxide
US5712235A (en) * 1993-09-15 1998-01-27 Henkel Kommanditgesellschaft Auf Aktien Bar soaps
US5739092A (en) * 1992-09-01 1998-04-14 The Procter & Gamble Company Liquid or gel dishwashing detergent containing alkyl ethoxy carboxylate divalent ok ions and alkylpolyethoxypolycarboxylate
US5750748A (en) * 1993-11-26 1998-05-12 The Procter & Gamble Company N-alkyl polyhydroxy fatty acid amide compositions and their method of synthesis
DE19749560A1 (de) * 1997-11-10 1999-06-10 Henkel Kgaa Hautfreundliche Handgeschirrspülmittel
US5932535A (en) * 1995-12-21 1999-08-03 Henkel Kommanditgesellschaft Auf Aktien Process for the production of light-colored, low-viscosity surfactant concentrates
US5965516A (en) * 1993-11-26 1999-10-12 The Procter & Gamble Company N-alkyl polyhydroxy fatty acid amide compositions and their method of synthesis
US6264961B1 (en) 1995-09-11 2001-07-24 Henkel Kommanditgesellschaft Auf Aktien Oil-water emulsifiers
EP1167500A1 (fr) * 2000-06-29 2002-01-02 The Procter & Gamble Company Procédé pour le nettoyage d'une surface dure
US6846796B2 (en) 2000-04-15 2005-01-25 Cognis Deutschland Gmbh & Co. Kg Method for producing non-ionic tenside granulates
DE102005025933B3 (de) * 2005-06-06 2006-07-13 Centrotherm Photovoltaics Gmbh + Co. Kg Dotiergermisch für die Dotierung von Halbleitern
US8785366B2 (en) 2008-05-23 2014-07-22 Colgate-Palmolive Company Liquid cleaning compositions and methods

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Cited By (66)

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Publication number Priority date Publication date Assignee Title
WO1993005132A1 (fr) * 1991-09-06 1993-03-18 The Procter & Gamble Company Compositions detergentes contenant du calcium et un amide d'acide gras polyhydroxy
TR26664A (tr) * 1991-09-06 1995-03-15 Procter & Gamble Kalsiyum ve polihidroksi yagli asit amidi ihtiva eden deterjan bilesimleri
TR26929A (tr) * 1992-06-02 1994-08-24 Procter & Gamble Bir anizotropik yüzey aktif cismi fazi iceren sulu deterjan bilesimleri.
EP0572723A1 (fr) * 1992-06-02 1993-12-08 The Procter & Gamble Company Compositions détergentes liquides structurées
EP0656046A4 (fr) * 1992-08-21 1995-09-20 Procter & Gamble Composition concentree de detergent liquide comprenant un sulfate d'ether d'alkyle et son procede de preparation.
TR27633A (tr) * 1992-08-21 1995-06-14 Procter & Gamble Konsantre sivi deterjan bilesimi ve bilesimin imalati icin bir islem.
EP0656046A1 (fr) * 1992-08-21 1995-06-07 The Procter & Gamble Company Composition concentree de detergent liquide comprenant un sulfate d'ether d'alkyle et son procede de preparation
EP0658188A1 (fr) * 1992-09-01 1995-06-21 The Procter & Gamble Company Compositions detergentes liquides ou en gel contenant du calcium et stabilisant de celles-ci
US5739092A (en) * 1992-09-01 1998-04-14 The Procter & Gamble Company Liquid or gel dishwashing detergent containing alkyl ethoxy carboxylate divalent ok ions and alkylpolyethoxypolycarboxylate
WO1994005755A1 (fr) * 1992-09-01 1994-03-17 The Procter & Gamble Company Liquide ou gel detergent pour la vaisselle contenant un amide d'acide gras polyhydroxy, des ions de calcium et un alkylpolyethoxypolycarboxylate
WO1994005758A1 (fr) * 1992-09-01 1994-03-17 The Procter & Gamble Company Compositions detergentes liquides ou en gel contenant du calcium et stabilisant de celles-ci
WO1994005752A3 (fr) * 1992-09-01 1994-04-14 Procter & Gamble Composition detersive liquide ou en gel pour lave-vaisselle, contenant de l'acide amphocarboxylique d'alkyle et des ions de magnesium ou de calcium
US5545354A (en) * 1992-09-01 1996-08-13 The Procter & Gamble Company Liquid or gel dishwashing detergent containing a polyhydroxy fatty acid amide, calcium ions and an alkylpolyethoxypolycarboxylate
US5580849A (en) * 1992-09-01 1996-12-03 The Procter & Gamble Company Liquid or gel detergent compositions containing calcium and stabilizing agent thereof
EP0658188A4 (fr) * 1992-09-01 1995-08-09 Procter & Gamble Compositions detergentes liquides ou en gel contenant du calcium et stabilisant de celles-ci.
US5269974A (en) * 1992-09-01 1993-12-14 The Procter & Gamble Company Liquid or gel dishwashing detergent composition containing alkyl amphocarboxylic acid and magnesium or calcium ions
TR27708A (tr) * 1992-09-01 1995-06-22 Procter & Gamble Kalsiyum ve buna ait stabilize edici madde ihtiva eden sivi veya jel deterjan terkipleri.
US5716922A (en) * 1992-11-04 1998-02-10 The Procter & Gamble Company Detergent gels
WO1994010273A1 (fr) * 1992-11-04 1994-05-11 The Procter & Gamble Company Gels detersifs
TR28437A (tr) * 1992-11-04 1996-06-19 Procter & Gamble Elde yikanan bulasik icin jel deterjanlar.
GB2272223A (en) * 1992-11-04 1994-05-11 Procter & Gamble Detergent gels
WO1994012598A1 (fr) * 1992-11-30 1994-06-09 The Procter & Gamble Company Compositions nettoyantes comprenant des tensioactifs non ioniques/anioniques d'amides d'acide gras polyhydroxy melanges, a faible pouvoir moussant
WO1994014947A1 (fr) * 1992-12-28 1994-07-07 The Procter & Gamble Company Gels detergents clairs
US5607910A (en) * 1993-06-30 1997-03-04 Sherry; Alan E. Detergent gels containing ethoxylated alkyl sulfates and secondary sulfonates
US5691300A (en) * 1993-07-12 1997-11-25 Henkel Kommanditgesellschaft Auf Aktien Rinse aids for the machine washing of hard surfaces
WO1995006106A1 (fr) * 1993-08-27 1995-03-02 The Procter & Gamble Company Compositions detergentes concentrees utilisees pour le lavage de la vaisselle, sous forme de liquide ou de gel, contenant des ions calcium et des tensioactifs de disulfonate
US5417893A (en) * 1993-08-27 1995-05-23 The Procter & Gamble Company Concentrated liquid or gel light duty dishwashing detergent compositions containing calcium ions and disulfonate surfactants
US5415814A (en) * 1993-08-27 1995-05-16 The Procter & Gamble Company Concentrated liquid or gel light duty dishwashing detergent composition containing calcium xylene sulfonate
WO1995006108A1 (fr) * 1993-08-27 1995-03-02 The Procter & Gamble Company Composition detergente concentree pour le lavage de la vaisselle , se presentant sous forme de liquide ou de gel, et contenant du sulfonate de xylene de calcium
US5474710A (en) * 1993-08-27 1995-12-12 Ofosu-Asanta; Kofi Process for preparing concentrated surfactant mixtures containing magnesium
WO1995006107A1 (fr) * 1993-08-27 1995-03-02 The Procter & Gamble Company Compositions detergentes concentrees, se presentant sous forme de liquide ou de gel, et contenant du sucre pour lavages delicats tels que le lavage de la vaisselle
WO1995006103A1 (fr) * 1993-08-27 1995-03-02 The Procter & Gamble Company Procede de preparation de melanges de tensioactifs concentres contenant du magnesium
US5500150A (en) * 1993-09-09 1996-03-19 The Procter & Gamble Company Solidified detergent additive with n-alkoxy polyhydroxy fatty acid amide and alkoxylated surfactant
WO1995007330A1 (fr) * 1993-09-09 1995-03-16 The Procter & Gamble Company Detergent de lave-vaisselle automatique contenant un tensioactif d'amide alcoxy ou aryloxy
US5489393A (en) * 1993-09-09 1996-02-06 The Procter & Gamble Company High sudsing detergent with n-alkoxy polyhydroxy fatty acid amide and secondary carboxylate surfactants
WO1995007337A1 (fr) * 1993-09-09 1995-03-16 The Procter & Gamble Company Detergent extremement savonnant comprenant un amide d'acide gras n-alkoxy polyhydroxy et des tensioactifs de carboxylate secondaire
US5698046A (en) * 1993-09-09 1997-12-16 The Procter & Gamble Comapny Automatic dishwashing detergent with alkoxy or aryloxy amide surfactant
WO1995007971A1 (fr) * 1993-09-14 1995-03-23 The Procter & Gamble Company Detergents doux additionnes de protease, sous forme liquide ou de gel
US5712235A (en) * 1993-09-15 1998-01-27 Henkel Kommanditgesellschaft Auf Aktien Bar soaps
US5965516A (en) * 1993-11-26 1999-10-12 The Procter & Gamble Company N-alkyl polyhydroxy fatty acid amide compositions and their method of synthesis
US5750748A (en) * 1993-11-26 1998-05-12 The Procter & Gamble Company N-alkyl polyhydroxy fatty acid amide compositions and their method of synthesis
US5789372A (en) * 1994-01-12 1998-08-04 Henkel Kommanditgesellschaft Auf Aktien Surfactant mixtures having improved surface-active properties
DE4400632C1 (de) * 1994-01-12 1995-03-23 Henkel Kgaa Tensidgemische und diese enthaltende Mittel
US5512699A (en) * 1994-01-25 1996-04-30 The Procter & Gamble Company Poly polyhydroxy fatty acid amides
US5669984A (en) * 1994-01-25 1997-09-23 The Procter & Gamble Company Method for hand washing dishes containing polyhydroxy amines
US5698505A (en) * 1994-01-25 1997-12-16 The Procter & Gamble Company High sudsing light duty liquid or gel dishwashing detergent compositions containing long chain amine oxide
US5534197A (en) * 1994-01-25 1996-07-09 The Procter & Gamble Company Gemini polyhydroxy fatty acid amides
US5500155A (en) * 1994-03-18 1996-03-19 Henkel Kommanditgesellschaft Auf Aktien Detergent mixtures of fatty acid isethionate salts and fatty alcohols
US5942485A (en) * 1994-05-06 1999-08-24 The Procter & Gamble Company Stable concentrated liquid laundry detergent composition containing alkyl polyethoxylate sulfate and polyhydroxy fatty acid amide surfactants and toluene sulfonate salt
WO1995030730A1 (fr) * 1994-05-06 1995-11-16 The Procter & Gamble Company Detergent liquide contenant un amide polyhydroxyle d'acide gras et un sel toluene sulfonate
WO1996001306A1 (fr) * 1994-07-05 1996-01-18 The Procter & Gamble Company Composition detergente pour le lavage de linge a la main possedant une douceur et des qualites de nettoyage ameliorees
USH1632H (en) * 1994-08-15 1997-02-04 Shell Oil Company Liquid laundry detergent formulations
US5686603A (en) * 1995-05-04 1997-11-11 Lever Brothers Company, Division Of Conopco, Inc. Sulfated polyhydroxy compounds as anionic surfactants and a process for their manufacture
US6264961B1 (en) 1995-09-11 2001-07-24 Henkel Kommanditgesellschaft Auf Aktien Oil-water emulsifiers
EP0776653A1 (fr) 1995-11-30 1997-06-04 Henkel Kommanditgesellschaft auf Aktien Compositions cosmétiques et/ou pharmaceutiques contenant des amides d'acides gras polyhydroxyle
US5932535A (en) * 1995-12-21 1999-08-03 Henkel Kommanditgesellschaft Auf Aktien Process for the production of light-colored, low-viscosity surfactant concentrates
EP0780464A2 (fr) 1995-12-21 1997-06-25 Henkel Kommanditgesellschaft auf Aktien Procédé pour la préparation des concentrés d'agents tensio-actifs de couleur claire à basse viscosité
WO1997038071A1 (fr) * 1996-04-08 1997-10-16 Colgate-Palmolive Company Compositions liquides detergentes pour lavages delicats
DE19749560A1 (de) * 1997-11-10 1999-06-10 Henkel Kgaa Hautfreundliche Handgeschirrspülmittel
DE19749560C2 (de) * 1997-11-10 2002-01-10 Henkel Kgaa Hautfreundliche Handgeschirrspülmittel
US6846796B2 (en) 2000-04-15 2005-01-25 Cognis Deutschland Gmbh & Co. Kg Method for producing non-ionic tenside granulates
EP1167500A1 (fr) * 2000-06-29 2002-01-02 The Procter & Gamble Company Procédé pour le nettoyage d'une surface dure
WO2002002723A1 (fr) * 2000-06-29 2002-01-10 The Procter & Gamble Company Procede de nettoyage d'une surface dure
DE102005025933B3 (de) * 2005-06-06 2006-07-13 Centrotherm Photovoltaics Gmbh + Co. Kg Dotiergermisch für die Dotierung von Halbleitern
US8043946B2 (en) 2005-06-06 2011-10-25 Centrotherm Photovoltaics Ag Mixture for doping semiconductors
US8785366B2 (en) 2008-05-23 2014-07-22 Colgate-Palmolive Company Liquid cleaning compositions and methods

Also Published As

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ES2077247T3 (es) 1995-11-16
FI931369A0 (fi) 1993-03-26
TR26013A (tr) 1993-11-01
GR3017416T3 (en) 1995-12-31
TW265361B (fr) 1995-12-11
NZ240022A (en) 1995-03-28
JPH06501729A (ja) 1994-02-24
GB9021217D0 (en) 1990-11-14
CN1042236C (zh) 1999-02-24
DE69113055D1 (de) 1995-10-19
EP0550636A1 (fr) 1993-07-14
HU213448B (en) 1997-06-30
ATE127834T1 (de) 1995-09-15
CZ281716B6 (cs) 1996-12-11
JP3007150B2 (ja) 2000-02-07
CO4180440A1 (es) 1995-06-07
KR100221444B1 (ko) 1999-09-15
DE69113055T2 (de) 1996-04-04
PT99087B (pt) 2001-05-31
MA22303A1 (fr) 1992-04-01
NO931078D0 (no) 1993-03-24
DK0550636T3 (da) 1996-02-05
PT99087A (pt) 1992-08-31
AU664023B2 (en) 1995-11-02
SK25393A3 (en) 1993-07-07
IE913404A1 (en) 1992-04-08
IN185274B (fr) 2000-12-16
AR244328A1 (es) 1993-10-29
IE76141B1 (en) 1997-10-08
MY108070A (en) 1996-08-15
CA2092194C (fr) 1996-11-19
MX9101373A (es) 1992-05-04
CN1062160A (zh) 1992-06-24
NO931078L (no) 1993-05-27
FI931369A7 (fi) 1993-04-26
EP0550636B1 (fr) 1995-09-13
HU9300888D0 (en) 1993-07-28
CA2092194A1 (fr) 1992-03-29
BR9106935A (pt) 1993-08-17
AU8735291A (en) 1992-04-28
EG19516A (en) 1995-08-30
HUT64390A (en) 1993-12-28
CZ53393A3 (en) 1994-10-19

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