WO1995020026A1 - Compositions de detergents liquides de lavage de vaisselle - Google Patents

Compositions de detergents liquides de lavage de vaisselle Download PDF

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Publication number
WO1995020026A1
WO1995020026A1 PCT/US1995/000768 US9500768W WO9520026A1 WO 1995020026 A1 WO1995020026 A1 WO 1995020026A1 US 9500768 W US9500768 W US 9500768W WO 9520026 A1 WO9520026 A1 WO 9520026A1
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WO
WIPO (PCT)
Prior art keywords
alkyl
moieties
surfactant
branched
liquid dishwashing
Prior art date
Application number
PCT/US1995/000768
Other languages
English (en)
Inventor
Peter Robert Foley
Joanna Margaret Clarke
Yi-Chang Fu (Nmn)
Phillip Kyle Vinson
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
Priority claimed from US08/342,558 external-priority patent/US5534197A/en
Priority claimed from GBGB9425942.1A external-priority patent/GB9425942D0/en
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to MX9602985A priority Critical patent/MX9602985A/es
Priority to CA002179709A priority patent/CA2179709C/fr
Priority to US08/669,545 priority patent/US5888955A/en
Priority to EP95908587A priority patent/EP0741773A4/fr
Publication of WO1995020026A1 publication Critical patent/WO1995020026A1/fr

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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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0094—High foaming compositions
    • 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
    • C11D1/645—Mixtures of compounds all of which are cationic
    • 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
    • C11D1/835—Mixtures of non-ionic with cationic 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
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/94—Mixtures with anionic, cationic or 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/04—Carboxylic acids or salts thereof
    • 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
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/526—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 are polyalkoxylated
    • 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
    • C11D1/528—Carboxylic amides (R1-CO-NR2R3), where at least one of the chains R1, R2 or R3 is interrupted by a functional group, e.g. a -NH-, -NR-, -CO-, or -CON- 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
    • C11D1/75—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

Definitions

  • the present invention relates to liquid detergent compositions, particularly to dishwashing compositions comprising a bridged polyhydroxy fatty acid amide which exhibit improved sudsing.
  • the formulator of a manual dishwashing detergent composition is required to formulate compositions which meet a number of consumer relevant performance demands. Firstly, such a composition should be effective at removing soils from dirty "dishes" when used in a manual dishwashing process.
  • the soils encountered in dishwashing are largely but not exclusively food based.
  • Particularly difficult soils to remove include greasy soils, burnt-or baked-on soils or those which have been allowed to harden onto the dish article, as well as non-food soils such as lipstick on the rims of glasses or nicotine stains.
  • the dishwashing detergent should act so as to suspend these soils in the wash solution and thus prevent their redeposition onto the dishes, or onto the surface of the sink.
  • the manual dishwashing composition should be high sudsing and the sudsing should persist throughout the washing process. This is particularly important as sudsing is used as an indicator by the consumer of the performance of the detergent composition. Moreover, the consumer also uses the sudsing profile as an indicator that the wash solution still contains active detergent ingredients and the consumer usually renews the wash solution when the sudsing subsides. Thus, a low sudsing formulation will tend to be replaced by the consumer more frequently than is necessary because of the low sudsing level.
  • the manual dishwashing composition should also be mild to the skin, and particularly to the hands and should not cause skin dryness, chapping or roughness. Such skin complaints largely result from the removal of natural oils from the skin.
  • the manual dishwashing composition should desirably be effective at removing grease from plates but not natural oils from the skin.
  • liquid detergent compositions may comprise certain co-surfactants such as long chain amine oxides, betaines, non-bridged polyhydroxy fatty acid amides and branched alkyl carboxylates, which have been found particularly effective in the removal of such soils, especially when present in high concentrations.
  • co-surfactants such as long chain amine oxides, betaines, non-bridged polyhydroxy fatty acid amides and branched alkyl carboxylates, which have been found particularly effective in the removal of such soils, especially when present in high concentrations.
  • co-surfactants such as long chain amine oxides, betaines, non-bridged polyhydroxy fatty acid amides and branched alkyl carboxylates, which have been found particularly effective in the removal of such soils, especially when present in high concentrations.
  • a disadvantage of such compounds is their tendency to reduce the overall sudsing profile of the detergent composition.
  • dishwashing composition which facilitates the removal of soils, especially oily and greasy soils and which produces a high and persistent level of sudsing.
  • Polyhydroxy fatty acid amides have been disclosed as surfactants in the art, see for example US 5 194 639, US 5 174 927 and US 5 188 769.
  • the present invention is a liquid dishwashing detergent composition
  • a surfactant system comprising a polyhydroxy fatty acid amide, characterised in that said system comprises a) a polyhydroxy fatty acid amide according to the formula:
  • R R' wherein X is a bridging group having from 2 to 200 atoms; Z and Z' are the same or different alcohol-containing moieties having two or more hydroxyl groups, or one of Z or Z' is hydrogen; and R and R are the same or different hydrocarbyl moieties having from 1 to 21 carbon atoms and can be saturated, branched or unsaturated and mixtures thereof and b) a co-surfactant selected from C ⁇ to Cjg amine oxides, C10-C16 branched alkyl carboxylates, C ⁇ -Cis betaines and non bridged polyhydroxy fatty acid amides and mixtures thereof.
  • the present invention is a liquid dishwashing detergent composition
  • a liquid dishwashing detergent composition comprising at least 1%, preferably from 10% to 60%, more preferably from 20% to 50% of a surfactant system.
  • the surfactant system comprises as an essential component a co-surfactant selected from C]6 to Cj8 amine oxides, C ⁇ Q-C ⁇ branched alkyl carboxylates C ⁇ -C ⁇ % betaines and non bridged polyhydroxy fatty acid amides and mixtures thereof.
  • the compositions of the present invention comprise from 0.1% to 40%, preferably from 1% to 10%, most preferably from 2% to 8% of said co-surfactant.
  • amine oxides suitable for use herein have the formula:
  • R ⁇ is selected from an alkyl, hydroxyalkyl, acylamidopropyl and alkyl phenyl group, or mixtures thereof, containing from 16 to 18 carbon atoms; and R2 and R3 are independently C1-.3 alkyl or C2-3 hydroxyalkyl groups, or a polyethylene oxide group containing from 1 to 3, preferably 1, ethylene oxide groups.
  • These amine oxide surfactants in particular include C16-C18 alkyl dimethyl amine oxides and C16-C18 alkoxy ethyl dihydroxyethyl amine oxides.
  • the compositions comprise from 0.1% to 20%, preferably from 0.5% to 10%, most preferably from 1% to 5% of said amine oxide.
  • Alkyl carboxylates useful herein are those which contain a carboxyl unit connected to a secondary carbon. It is to be understood herein that the secondary carbon can be in a ring structure, e.g. as in p-octyl benzoic acid, or as in alkyl-substituted cyclohexyl carboxylates. These surfactants should contain no ether linkages, no ester linkages and no hydroxyl groups. There should be no nitrogen atoms in the head-group (amphiphilic portion).
  • the alkyl carboxylate surfactants usually contain 11-15, preferably from 11 to 13 total carbon atoms, although slightly more (e.g., up to 16) can be tolerated,- e.g. p-octyl benzoic acid.
  • a highly preferred class of alkylcarboxylates comprises the secondary carboxyl materials of the formula R3 CH(R 4 )COOM, wherein R ⁇ is CH3(CH2)x and R 4 is CH3(CH2)y, wherein y can be O or an integer from 1 to 4, x is an integer from 4 to 10 and the sum of (x + y) is 6-14, preferably 7- 13, most preferably 8-10.
  • alkylcarboxylate soaps useful herein comprises those carboxyl compounds wherein the carboxyl substituent is on a ring hydrocarbyl unit, i.e., secondary soaps of the formula R5-R6-COOM, wherein R ⁇ is C ⁇ -C ⁇ , preferably C ⁇ -C ⁇ , alkyl or alkenyl and R > is a ring structure, such as benzene, cyclopentane and cyclohexane. (Note: R ⁇ can be in the ortho, meta or para position relative to the carboxyl on the ring.)
  • a further class of alkyl carboxylates comprises secondary carboxyl compounds of the formula CH3(CHR)k-(CH2)m-(CHR)n- CH(COOM)(CHR) 0 -(CH2)p-(CHR)q-CH3, wherein each R is C1-C4 alkyl, wherein k, n, 0, q are integers in the range of 0-8, provided that the total number of carbon atoms (including the carboxylate) is in the range of 10 to 18.
  • M can be any suitable, especially water-solubilizing, counterion, e.g., H, alkali metal, alkaline earth metal, ammonium, alkanolammomum, di- and tri- alkanolammonium, and C1-C5 alkyl substituted ammonium.
  • Sodium is convenient, as is diethanolammonium.
  • Preferred alkyl carboxylates for use herein are water-soluble members selected from the group consisting of the water-soluble salts of 2- methyl-1-undecanoic acid, 2-ethyl-l-decanoic acid, 2-propyl-l-nonanoic acid, 2-butyl-l-octanoic acid, 2-pentyl-l-heptanoic acid and isopentadecanoic acid.
  • compositions comprise from 0.1% to 20%, preferably from 0.5% to 10% of said branched alkyl carboxylate.
  • non bridged polyhydroxy fatty acid amides suitable for use herein are according to the formula:
  • Ri is H, a C ⁇ .C hydrocarbyl, 2-hydroxy ethyl, 2-hydroxy propyl or mixtures thereof, preferably a C ..C4 alkyl, more preferably a C ⁇ or C2 alkyl, most preferably a
  • R2 is a C1-C21 hydrocarbyl, preferably straight chain C7-C19 alkyl or alkenyl, most preferably straight chain CJO- C ⁇ g alkyl or alkenyl or mixtures thereof; and Z is a polyhydrocarbyl having a linear hydrocarbyl chain with at least 2 hydroxyl groups directly connected to the chain or an alkoxylated derivative thereof.
  • Z is preferably derived from a reducing sugar in reductive amination reaction; more preferably Z is a glycityl.
  • Suitable reducing sugars include glucose, fructose, maltose, lactose, galactose, mannose and xylose.
  • high dextrose corn syrup, high fructose corn syrup and high maltose corn syrup can be utilised as well as individual sugars listed above. It should be understood that these corn syrups may yield a mixture of sugar components for Z.
  • Z is preferably selected from the group consisting of
  • nCH2 ⁇ H -CH(CH2 ⁇ H)-(CHOH)n-l ⁇ CH 2 OH
  • R ⁇ can be for example, N-methyl , N-ethyl, N-propyl, N-isopropyl, N-butyl, N-2-hydroxy ethyl, or N-2-hydroxy propyl.
  • R5-CO-N ⁇ can be for example cocamide, stearimide, oleamide, lauramide, myristamide, capricamide, palmitamide, talloamide etc.
  • Z can be 1- deoxyglycityl, 2-deoxyfructityl, 1-deoxymaltityl, 1-deoxylactityl, 1- deoxygalactityl, 1-doexymannityl, 1-deoxymaltotriotityl, etc.
  • the compositions may comprise from 0.1% to 30%, preferably from 1% to 20%, most preferably from 3% to 10% of said polyhydroxy fatty acid amide.
  • the betaines useful herein are those compounds having the formula R(Rl)2N + R2COO" wherein R is a C6-C18 hydrocarbyl group, preferably a C10- 6 alkyl group or C10-I6 acylamido alkyl group, each R is typically C1-C3 alkyl, preferably methyl, and R2 is a C1-C5 hydrocarbyl group, preferably a C1-C3 alkylene group, more preferably a C1-C2 alkylene group.
  • betaines examples include coconut acylamidopropyldimethyl betaine; hexadecyl dimethyl betaine; Cj2- 14 acylamidopropylbetaine; C8-14 acylamidohexyldiethyl betaine; 4[Ci4_i6 acylmethy lamidodiethylammonio] - 1 -carboxybutane; C ⁇ 6_i8 acylamidodimethylbetaine; C12-I6 acylamidopentanediethyl-betaine;[Ci2- 16 acylmethylamidodimethylbetaine.
  • Preferred betaines are C 2-I8 dimethyl-ammonio hexanoate and the C10-I8 acylamidopropane (or ethane) dimethyl (or diethyl) betaines.
  • the complex betaines suitable for use herein have the formula:
  • R is a hydrocarbon group having from 7 to 22 carbon atoms, preferably 12 to 14 carbon atoms
  • A is the group (C(O))
  • n is 0 or 1
  • Ri is hydrogen or a lower alkyl group
  • x is 2 or 3
  • y is an integer of 0 to 4
  • Q is the group -R2COOM wherein R2 is an alkylene group having from 1 to 6 carbon atoms and M is hydrogen or an ion from the groups alkali metals, alkaline earth metals, ammonium and substituted ammonium and B is hydrogen or a group Q as defined.
  • the composition may comprise from 0.1% to 10%, preferably from 0.1% to 5% of said betaines.
  • the sudsing performance of said liquid dishwashing detergent composition can be improved by the addition of a bridged polyhydroxy fatty acid amide.
  • the bridged polyhydroxy fatty acid amide has the formula:
  • X is a bridging group having from about 2 to about 200 atoms
  • Z and Z' are the same or different alcohol-containing moieties having two or more hydroxyl groups (e.g., glycerol, and units derived from reducing sugars such as glucose, maltose and the like), or either one (but not both) of Z or Z' is hydrogen
  • R and R' are the same or different hydrocarbyl moieties having from about 1 to about 13 carbon atoms and can be saturated, branched or unsaturated (e.g., oleoyl) and mixtures thereof.
  • Preferred X groups are selected from substituted or unsubstituted, branched or linear alkyl, ether alkyl, amino alkyl, or amido alkyl moieties having from about 2 to about 15 carbon atoms.
  • Preferred alkyl moieties are unsubstituted, linear alkyl moieties having the formula -(CH2) n -, wherein n is an integer from 2 to about 15, preferably from 2 to about 10, and most preferably from 2 to about 6; and also unsubstituted, branched alkyl moieties having from 3 to about 15 carbon atoms, preferably from 3 to about 10 carbon atoms, and most preferably from 3 to about 6 carbon atoms.
  • ethylene and propylene (branched or linear) alkyl moieties are also preferred.
  • unsubstituted, branched or linear ether alkyl moieties having the formula - R2-(0-R2) m -, wherein each R2 is independently selected from C2-C8 branched or linear alkyl and/or aryl moieties (preferably ethyl, propyl or combinations thereof) and m is an integer from 1 to about 5.
  • X may also be unsubstituted, branched or linear amino and/or amido alkyl moieties having the formula -R2-(N(R3)-R2) m -, wherein each R2 is independently selected from C2-C8 branched or linear alkyl and/or aryl moieties (preferably ethyl, propyl or combinations thereof), m is an integer from 1 to about 5, and R ⁇ is selected from hydrogen, C1-C5 alkyl, and -C(0)R 4 -, wherein R 4 is C1-C21 alkyl, including -C(0)R.
  • the X moiety may be derived from commercially available amine compounds such as, for example, JeffaminesR (supplied by Texaco) such as JED600, JEDR148, JEDR192, JED230, JED2000, J-D230 and J-D400.
  • JeffaminesR supplied by Texaco
  • Preferred X moieties therefore include: -(CH2)2-, -(CH2)3-, -(CH2)4-, - (CH 2 )5-, -(CH 2 )6-, -CH 2 CH(CH 3 )(CH 2 )3-, -(CH 2 ) 2 -0-(CH 2 )2-, -(CH 2 ) 3 - 0-(CH 2 )3-, -(CH 2 )2-0-(CH 2 )3-, -(CH 2 )2-0-(CH2)2-0-(CH 2 )2-, -(CH 2 ) 3 - 0-(CH2)2-0-(CH 2 )3-, -(CH2)2-0-(CH2)3-0-(CH2)2-, -(CH2)2-NH-(CH2)2- , -(CH 2 )3-NH-(CH 2 )3-, -(CH 2 )2-NH-(CH 2 )3-, -(CH 2 )2-N(C(0)RMCH
  • Preferred Z and Z' groups are independently selected from polyhydroxyhydrocarbyl moieties having a linear hydrocarbyl chain with at least 2 hydroxyls (in the case of glycerol) or at least 3 hydroxyls ( in the case of other sugars) directly connected to the chain, or an alkoxylated derivative (preferably ethoxylated or propoxylated) thereof.
  • Z and Z' preferably will be derived from a reducing sugar, more preferably Z and/or Z' is a glycityl moiety.
  • Suitable reducing sugars include glucose, fructose, maltose, lactose, galactose, mannose, and xylose, as well as glyceraldehyde.
  • high dextrose com sy p high fructose com sy p
  • high maltose com sy p can be utilised as well as the individual sugars listed above.
  • These com syrups may yield a mix of sugar components for Z and Z. It should be understood that it is by no means intended to exclude other suitable raw materials.
  • Z and/or Z' preferably will be selected from the group consisting of -CH 2 -(CH0H)- p -CH20H, -CH(CH 2 0H)-(CH0H) p . ⁇ -CH20H, -CH - (CH0H)2(CH0Rl)(CH0H)-CH20H, where p is an integer from 1 to 5, inclusive, and Rl is H or a cyclic mono- or polysaccharide, and alkoxylated derivatives thereof. Most preferred are glycityls wherein p is 4, particularly - CH2-(CH0H)4-CH20H.
  • R and R groups are independently selected from C3-C21 hydrocarbyl moieties, preferably straight or branched chain C3-C13 alkyl or alkenyl, more preferably straight chain C5-C11 alkyl or alkenyl, most preferably straight chain C5-C9 alkyl or alkenyl, or mixtures thereof.
  • R-CO- N ⁇ and/or R'-CO-N ⁇ can be, for example, cocamide, stearamide, oleamide, lauramide, myristamide, capricamide, palmitamide, tallowamide, etc.
  • compositions according to the present invention comprise from at least 0.05%, preferably from 0.1% to 30% , more preferably from 0.5% to 20%, most preferably from 1% to 10%, of said bridged polyhydroxy fatty acid amide.
  • the composition preferably comprises said bridged polyhydroxy fatty acid amides and said co-surfactant in a ratio of from 1:50 to 50:1, preferably from 1:10 to 10:1, more preferably from 1:5 to 5:1.
  • the detergent composition comprises a surfactant system, said system may comprise at least one additional surfactant (other than a polyhydroxyfatty acid amide (a) and amine oxide, betaine, non bridged polyhydroxyfatty acid amide or branched alkylcarboxylate (b)), the selected from anionic, nonionic, amphoteric and zwiterionic surfactants and mixtures thereof.
  • additional surfactant other than a polyhydroxyfatty acid amide (a) and amine oxide, betaine, non bridged polyhydroxyfatty acid amide or branched alkylcarboxylate (b)
  • Suitable nonionic detergent surfactants for use herein include nonionic condensates of alkyl phenols, nonionic ethoxylated alcohols and nonionic fatty acid amides. According to the present invention the compositions may comprise from 0% to 30%, preferably from 0.1% to 25%, more preferably from 0.5% to 20% of said nonionic surfactants.
  • polyethylene, polypropylene, and polybutylene oxide condensates of alkyl phenols are suitable for use herein.
  • the polyethylene oxide condensates are preferred.
  • These compounds include the condensation products of alkyl phenols having an alkyl group containing from about 6 to about 12 carbon atoms in either a straight chain or branched chain configuration with the alkylene oxide.
  • the alkyl ethoxylate condensation products of aliphatic alcohols with from about 1 to about 25 moles of ethylene oxide are suitable for use herein.
  • the alkyl chain of the aliphatic alcohol can either be straight or branched, primary or secondary, and generally contains from 6 to 22 carbon atoms.
  • Particularly preferred are the condensation products of alcohols having an alkyl group containing from 8 to 20 carbon atoms with from about 2 to about 10 moles of ethylene oxide per mole of alcohol.
  • Most preferred are the condensation products of alcohols having an alkyl group containing from 8 to 14 carbon atoms with from about 6 to about 10 moles of ethylene oxide per mole of alcohol.
  • nonionic surfactants of this type include TergitolTM 15-S-9 (the condensation product of Ci ⁇ -Ci5 linear alcohol with 9 moles ethylene oxide), TergitolTM 24-L-6 NMW (the condensation product of C12-C14 primary alcohol with 6 moles ethylene oxide with a narrow molecular weight distribution), both marketed by Union Carbide Corporation; NeodolTM 45.9 (the condensation product of C14-C15 linear alcohol with 9 moles of ethylene oxide), NeodolTM 23-6.5 (the condensation product of C12-C13 linear alcohol with 6.54 moles of ethylene oxide), NeodolTM 45.7 (the condensation product of C14-C15 linear alcohol with 7 moles of ethylene oxide), NeodolTM 45.4 (the condensation product of C14-C15 linear alcohol with 4 moles of ethylene oxide), NeodolTM23-3 (the condensation product of C12-C13 linear alcohol with 3 moles of ethyene oxide) marketed by Shell Chemical Company, KyroTM EO
  • condensation products of ethylene oxide with a hydrophobic base formed by the condensation of propylene oxide with propylene glycol are suitable for use herein.
  • examples of compounds of this type include certain of the commercially-available PluronicTM surfactants, marketed by BASF.
  • condensation products of ethylene oxide with the product resulting from the reaction of propylene oxide and ethylenediamine are suitable for use herein.
  • this type of nonionic surfactant include certain of the commercially available TetronicTM compounds, marketed by BASF.
  • the composition may comprise as an optional ingredient, alkylpolysaccharides i.e. nonionic alkylpolysaccharides or the corresponding sulphated polysaccharides and mixtures thereof.
  • alkylpolysaccharides suitable for use herein are disclosed in U.S.
  • Patent 4,565,647, Llenado having a hydrophobic group containing from about 6 to about 30 carbon atoms, preferably from about 11 to about 30, more preferably 11 to 16 carbon atoms and a polysaccharide, e.g., a polyglycoside, hydrophilic group containing from about 1.0 to about 10, preferably from about 1.0 to about 3, most preferably from about 1.3 to about 2.7 saccharide units.
  • Any reducing saccharide containing 5 or 6 carbon atoms can be used, e.g., glucose, galactose and galactosyl moieties can be substituted for the glucosyl moieties.
  • the hydrophobic group is attached at the 2-, 3-, 4-, etc. positions thus giving a glucose or galactose as opposed to a glucoside or galactoside.
  • the intersaccharide bonds can be, e.g., between the one position of the additional saccharide units and the 2-, 3-, 4-, and/or 6- positions on the preceding saccharide units.
  • the preferred alkyleneoxide is ethylene oxide.
  • Typical hydrophobic groups include alkyl groups, either saturated or unsaturated, branched or unbranched containing from 8 to 18, preferably from 10 to 16, carbon atoms.
  • the alkyl group is a straight-chain saturated alkyl group.
  • the alkyl group can contain up to about 3 hydroxyl groups and/or the polyalkyleneoxide chain can contain up to about 10, preferably less than 5, alkyleneoxide moieties.
  • Suitable alkyl polysaccharides are octyl, nonyldecyl, undecyldodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, and octadecyl, di-, tri-, terra-, penta-, and hexaglucosides, galactoses.
  • Suitable mixtures include coconut alkyl, di-, tri-, terra-, and pentaglucosides and tallow alkyl tetra-, penta- and hexaglucosides.
  • the preferred alkylpolyglycosides have the formula: R2 ⁇ (C n H 2n O)t(glycosyl) x
  • R2 is selected from the group consisting of alkyl, alkylphenyl, hydroxyalkyl, hydroxyalkylphenyl, and mixtures thereof in which the alkyl groups contain from 10 to 18, preferably from 12 to 14, carbon atoms; n is 0-3 preferably 2 to 3, t is from 0 to 10, preferably 0, x is from 1.0 to 10, preferably from 1.0 to 3, most preferably from 1.3 to 2.7.
  • the glycosyl is preferably derived from glucose. To prepare these compounds, the alcohol or alkylpolyethoxy alcohol is formed first and then reacted with glucose, or a source of glucose, to form the glucoside (attachment at the 1 -position). The additional glycosyl units can then be attached between their 1 -position and the preceding glycosyl units 2-, 3-, 4- and/or 6-position, preferably predominantly the 2-position.
  • the dishwashing compositions comprise from 0.5% to 50%, preferably from 1% to 30%, more preferably from 1.5% to 20% of said alkylpolysaccharide surfactant.
  • Anionic surfactant preferably from 1% to 30%, more preferably from 1.5% to 20% of said alkylpolysaccharide surfactant.
  • Anionic surfactants suitable for use herein may be essentially any anionic surfactant, including anionic sulphate, sulphonate or carboxylate surfactant.
  • the anionic sulphate surfactant may be any organic sulphate surfactant. It is preferably selected from the group consisting of C10-C16 alkyl sulphate which has been ethoxylated with from about 0.5 to about 20 moles of ethylene oxide per molecule, C9-C17 acyl-N-(C ⁇ -C4 alkyl) glucamine sulphate, C9-C ⁇ -N-(C2-C4 hydroxyalkyl) glucamine sulphate, and mixtures thereof, wherein the C9-C17 acyl group is derived from coconut dr palm kernel oil, as described in US patent 2 717 894.
  • the anionic sulphate surfactant is a C10-C16 alkyl sulphate which has been ethoxylated with from about 0.5 to about 12, moles of ethylene oxide per molecule.
  • the C10-C16 alcohol itself is commercially available.
  • C12-C14 alkyl sulphate which has been ethoxylated with from about 3 to about 10 moles of ethylene oxide per molecule is also preferred.
  • Blends can be made of material having different degrees of ethoxylation and/or different ethoxylate distributions arising from the specific ethoxylation techniques employed and subsequent processing steps such as distillation.
  • the counterion for the anionic sulphate surfactant component is preferably selected from calcium, sodium, potassium, magnesium, ammonium, or alkanol-ammonium, and mixtures thereof, with calcium and magnesium being preferred for cleaning and sudsing respectively.
  • Anionic alkyl ethoxy carboxylate surfactant Anionic alkyl ethoxy carboxylate surfactant
  • Alkyl ethoxy carboxylates suitable for use herein include those with the formula RO(CH2CH2 ⁇ )x CH2COO-M+ wherein R is a C12 to Ci6 alkyl group, x ranges from O to 10, and the ethoxylate distribution is such that, on a weight basis, the amount of material where x is 0 is less than 20%, preferably less than 15%, most preferably less than 10%, and the amount of material where x is greater than 7, is less than 25%, preferably less than 15%, most preferably less than 10%, the average x is from 2 to 4 when the average R is C13 or less, and the average x is from 3 to 6 when the average R is greater than C13, and M is a cation, preferably chosen from alkali metal, alkaline earth metal, ammonium mono., di-, and tri-ethanol- ammomum, most preferably from sodium, potassium, ammonium and mixtures thereof with magnesium ions.
  • Anionic alkyl polvethoxy polvcarboxylate surfactant Anionic alkyl polvethoxy polvcarboxylate surfactant
  • Alkyl polyethoxy polycarboxylate surfactants suitable for use herein include those having the formula:
  • R is a C to Ci8 alkyl group, x is from 1 to 25, Ri and R2 are selected from the group consisting of hydrogen, methyl acid radical, succinic acid radical, hydroxysuccinic acid radical, and mixtures thereof, wherein at least one R ⁇ or R2 is a succinic acid radical or hydroxysuccinic acid radical, and R3 is selected from the group consisting of hydrogen, substituted or unsubstituted hydrocarbon having between 1 and 8 carbon atoms, and mixtures thereof.
  • anionic surfactants useful for detersive purposes can also be included in the compositions hereof. These can include salts (including, for example, sodium, potassium, ammonium, and substituted ammonium salts such as mono-, di- and triethanolamine salts) of soap, fatty oleyl glycerol sulphates, alkyl phenol ethylene oxide ether sulphates, alkyl phosphates, alkyl succinates and sulphosuccinates, monoesters of sulphosuccinate (especially saturated and unsaturated C12-C18 monoesters) diesters of sulphosuccin ite (especially saturated and unsaturated C6-C 4 diesters), N- acyl C6_20 siircosinates.
  • salts including, for example, sodium, potassium, ammonium, and substituted ammonium salts such as mono-, di- and triethanolamine salts
  • soap fatty oleyl glycerol sulphates, alkyl
  • Resin acids and hydrogenated resin acids are also suitable, suc i as rosin, hydrogenated rosin, and resin acids and hydrogenated resin acids present in or derived from tall oil. Further examples are given in "Surface Active Agents and Detergents” (Vol. I and II by Schwartz, P ⁇ rry and Berch).
  • compositions according to the present invention comprise at least 3%, preferably from 3% to 40%, most preferably from 3% to 30% of said anionic surfactan s.
  • Suitable amphoteric surfactants for use herein include the alkyl amphocarboxylic acids of the formula:
  • R is a C8-C ⁇ g alkyl group, and R is of the general formula:
  • R 1 is a (CH2) x COOM or CH2CH2OH, and x is 1 or 2 and M is preferably chosen from alkali metal, alkaline earth metal, ammonium, mono- , di-, and tri-ethanolammonium, most preferably from sodium, potassium, ammonium and mixtures thereof with magnesium ions.
  • the preferred R alkyl chain length is a C10 to C14 alkyl group.
  • a preferred amphocarboxylic acid is produced from fatty imidazolines wherein the dicarboxylic acid functionality of the amphodicarboxylic acid is diacetic acid and/or dipropionic acid.
  • the detergent composition may comprise as optional ingredient other amine oxides according to the formula:
  • R ⁇ is selected from an alkyl, hydroxyalkyl, acylamidopropyl and alkyl phenyl group, or mixtures thereof, containing from 8 to 26 carbon atoms, preferably 8 to 16 carbon atoms;
  • R 4 is an alkylene or hydroxyalkylene group containing from 2 to 3 carbon atoms, preferably 2 carbon atoms, or mixtures thereof;
  • x is from 0 to 3, preferably 0;
  • each R5 is an alkyl or hydyroxyalkyl group containing from 1 to 3, preferably from 1 to 2 carbon atoms, or a polyethylene oxide group containing from 1 to 3, preferable 1, ethylene oxide groups.
  • the R ⁇ groups can be attached to each other, e.g., through an oxygen or nitrogen atom, to form a ring structure.
  • amine oxide surfactants in particular include C10-C14 alkyl dimethyl amine oxides and C -C12 alkoxy ethyl dihydroxyethyl amine oxides.
  • examples of such materials include diethyldecylamine oxide, bis-(2- hydroxyethyl)dodecylamine oxide, dimethyldodecylamine oxide, dipropyltetradecylamine oxide, dodecylamidopropyl dimethylamine oxide and dimethyl-2-hydroxyoctadecylamine oxide.
  • Preferred are C10-C14 alkyl dimethylamine oxide, and C10-I4 acylamido alkyl dimethylamine oxide.
  • the detergent composition may comprise from 0% to 20%, preferably from 1% to 10% of said amine oxide.
  • Zwitterionic surfactants can also be incorporated into the detergent compositions herein.
  • the sultaines useful in the present invention are those compounds having the formula (R(R1)2N + R2S03- wherein R is a C ⁇ -Ci ⁇ hydrocarbyl group, preferably a C10-C 6 alkyl group, more preferably a C12-C13 alkyl group, each R is typically C1-C3 alkyl, preferably methyl, and R2 is a Ci- C hydrocarbyl group, preferably a C1-C3 alkylene or, preferably, hydroxy alkylene group.
  • a hydrotrope is typically added to the compositions of the present invention, and may be present at levels of from 0% to 40%, preferably from l% to 15%, by weight.
  • Useful hydrotropes include sodium, potassium, calcium and ammonium salts of xylene sulphonate, toluene sulphonate and cumene sulphonate and mixtures thereof.
  • Other compounds useful as hydrotropes herein include polycarboxylates and urea. Some polycarboxylates have calcium chelating properties as well as hydrotropic properties.
  • alkylpolyethoxy polycarboxylate which can be employed herein is POLY-TERGENT C, Olin Corporation, Cheshire, CT, USA.
  • alkyl amphodicarboxylic acid of the generic formula:
  • R is a C% to Ci8 alkyl group
  • x is from 1 to 2
  • M is preferably chosen from alkali metal, alkaline earth metal, ammonium, mono-, di-, and tri-ethanolammonium, most preferably from sodium, potassium, ammonium, and mixtures thereof with magnesium ions.
  • the preferred alkyl chain length (R) is a Cio to C14 alkyl group and the dicarboxylic acid functionally is diacetic acid and/or dipropionic acid.
  • alkyl amphodicarboxylic acid is the amphoteric surfactant Miranol R 2CM Cone, manufactured by Miranol, Inc., Dayton, NJ, USA.
  • Organic solvent Suitable example of an alkyl amphodicarboxylic acid is the amphoteric surfactant Miranol R 2CM Cone, manufactured by Miranol, Inc., Dayton, NJ, USA.
  • compositions of the invention will most preferably contain an organic solvent system present at levels of from 1% to 30% by weight, preferably from 1% to 20% by weight, more preferably form 2% to 15% by weight of the composition.
  • the organic solvent system may be a mono, or mixed solvent system; but is preferably in mixed solvent system.
  • Suitable organic solvents for use herein have the general formula:
  • R is an alkyl, alkenyl, or alkyl aryl group having from 1 to 8 carbon atoms, and n is an integer from 1 to 4.
  • R is an alkyl group containing 1 to 4 carbon atoms, and n is 1 or 2.
  • R groups are n-butyl or isobutyl.
  • solvents useful herein include the water soluble CARBITOL or CELLOSOLVE solvents. These solvents are compounds of the 2-(2- alkoxyethoxy)ethanol class wherein the alkoxy group is derived from ethyl, propyl or butyl.
  • Suitable solvents are benzyl alcohol, and diols such as 2-ethyl- 1,3-hexanediol and 2,2,4-trimethl-l,3-pentanediol.
  • diols such as 2-ethyl- 1,3-hexanediol and 2,2,4-trimethl-l,3-pentanediol.
  • the low molecular weight, water-soluble, liquid polyethylene glycols are also suitable solvents for use herein.
  • alkane mono and diols especially the C1-C6 alkane mono and diols are suitable for use herein.
  • C1-C4 monohydric alcohols e.g.: ethanol, propanol, isopropanol, butanol and mixtures thereof
  • ethanol particularly preferred.
  • the C1-C4 dihydric alcohols, including propylene glycol, are also preferred. Thickening agents
  • compositions according to the present invention may additionally comprise thickening agents, such as polyquaternium cellulose cationic polymer, for example QuatrisoftR available from the Americhol Corporation.
  • thickening agents such as polyquaternium cellulose cationic polymer, for example QuatrisoftR available from the Americhol Corporation.
  • compositions according to the present invention may optionally comprise from 0.01% to 3%, more preferably from 0.15% to 0.9% of calcium ions. It has been found that the presence of calcium greatly improves the cleaning of greasy soils for compositions containing polyhydroxy fatty acid amide. This is especially true when the compositions are used in softened water, which contains few divalent ions.
  • the calcium ions can, for example, be added as a chloride, hydroxide, oxide, formate or acetate, or nitrate salt, xylene sulphonate, cumene sulphonate and toluene sulphonate. If the anionic surfactants are in the acid form, the calcium can be added as a calcium oxide or calcium hydroxide slurry in water to neutralise the acid.
  • the calcium ions may be present in the compositions as salts.
  • the amount of calcium ions present in compositions of the invention may be dependent upon the amount of total anionic surfactant present herein.
  • the molar ratio of calcium ions to total anionic surfactant is preferably from 1 :0.1 to 1 :25 more preferably from 1:2 to 1:10, for compositions of the invention.
  • malic, maleic or acetic acid, or their salts may be added to the composition of the present invention comprising calcium .
  • malic, maleic or acetic acid, or their salts can be added at levels of from 0.05% to 10% of the composition and a molar ratio with calcium of from 10: 1 to 1 : 10.
  • magnesium ions are preferably added to the liquid detergent compositions of the invention for improved product stability, as well as improved sudsing.
  • the magnesium can be added by neutralisation of the acid with a magnesium oxide or magnesium hydroxide slurry in water. Calcium can be treated similarly. This technique -minimises the addition of chloride ions, which reduces corrosive properties.
  • the neutralised surfactant salts and the hydrotrope are then added to the final mixing tank and any optional ingredients are added before adjusting the pH.
  • compositions according to the present invention formulated for use in manual dishwashing applications are preferably formulated to have a pH at 20°C of from 3 to 12, preferably from 6 to 9, most preferably from 6.5 to 8.5.
  • compositions may be formulated for use as in pre-treatment applications whereby the composition is applied in essentially the concentrated form onto the dishes.
  • the composition is allowed to remain on the dishes for a period of time.
  • Compositions for use in such applications preferably have a pH of from 3 to 14, more preferably from 3 to 5 or greater than 8.
  • the detergent compositions are liquid detergent compositions.
  • the compositions are high active formulations such that said compositions comprise 75% to 50% by weight, preferably from 70% to 55% by weight, most preferably from 65% to 55% by weight of a liquid carrier, e.g., water, preferably a mixture of water and a C1-C4 monohydric alcohol (e.g., ethanol, propanol, isopropanol, butanol, and mixtures thereof), with ethanol being the preferred monohydric alcohol or a mixture of water and C1-C4 dihydric alcohol (e.g.: propylene glycol).
  • the detergent composition may be in a concentrated form, such that the composition is diluted in water prior to usage.
  • the bridged poly hydroxy fatty acid amides of the present invention may be prepared by the following method.
  • Raney Ni (Grace Raney Nickel 4200) is contained in a 2 gallon reactor (316 stainless steel baffled autoclave with DISPERSIMAX hollow shaft multi- blade impeller) pressurized to about 300 psig with hydrogen at room temperature.
  • the nickel bed is covered with water taking up about 10% of the reactor volume. This is the first reductive amination run on the present load of nickel catalyst.
  • 606.53 g of 50 wt% ethylenediamine solution in water (5.05 moles, 1.00 mole equiv. of ethylenediamine) is maintained in a separate reservoir which is in closed communication with the reactor.
  • the reservoir is pressurized to about 100 psig with nitrogen.
  • 3636.36 g of 55 wt% D-glucose solution in water (11.1 moles, 2.20 mole equiv. of glucose) is maintained in a second separate reservoir which is also in closed communication with the reactor and is also pressurized to about 100 psig with nitrogen.
  • the ethylenediamine is loaded into the reactor from the reservoir using a high pressure pump. Once all the ethylenediamine is loaded into the reactor, stirring is begun and the reactor heated to 50 deg. C and pressurized to about 500 psig hydrogen.
  • the glucose solution is then loaded into the reactor from the reservoir using a high pressure pump similar to the amine pump above.
  • the pumping rate on the glucose pump can be varied and on this particular run, it is set to load the glucose in about 10 minutes.
  • the pressure is boosted to about 1300 psig hydrogen and the temperature raised to 60 deg. C for about 1 hour.
  • the temperature is then raised to 70 deg. C for 10 minutes, 80 deg. C for 10 minutes, 100 deg. C for 10 minutes, and finally 120 deg. C for 5 minutes, while maintaining hydrogen pressure between 1300-1500 psig.
  • the reactor is then cooled to 70 deg. C and the reaction solution removed from the reactor under hydrogen pressure via an internal dip tube and through a filter in closed communication with the reactor. Filtering under hydrogen pressure allows removal of any nickel particles without nickel dissolution.
  • Solid product is recovered by evaporation of water.
  • the product purity is approximately 85-90%. Sorbitol is the major impurity at about 10%.
  • the product can be used as is or purified to greater than 99%.
  • the cmde product is a viscous liquid with a purity of 70-80% which can be used as is or purified by column chromatography. Examples 1-4
  • compositions in accord with the invention were prepared.

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  • Engineering & Computer Science (AREA)
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  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)

Abstract

La présente invention concerne des compositions de détergents liquides de lavage de vaisselle comprenant un co-tensioactif appartenant au groupe des oxydes aminés, bétaïnes, carboxylates d'alkyle ramifiés et amides d'acides gras polyhydroxy non pontés. Lesdites compositions de lavage de vaisselle comportent en outre un amide d'acide gras polyhydroxy ponté améliorant le pouvoir moussant.
PCT/US1995/000768 1994-01-25 1995-01-20 Compositions de detergents liquides de lavage de vaisselle WO1995020026A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
MX9602985A MX9602985A (es) 1994-01-25 1995-01-20 Composiciones detergentes liquidas para lavado de vajilla.
CA002179709A CA2179709C (fr) 1994-01-25 1995-01-20 Compositions de detergents liquides de lavage de vaisselle
US08/669,545 US5888955A (en) 1994-12-22 1995-01-20 Liquid dishwashing detergent compositions
EP95908587A EP0741773A4 (fr) 1994-01-25 1995-01-20 Compositions de detergents liquides de lavage de vaisselle

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US18725194A 1994-01-25 1994-01-25
US08/187,251 1994-01-25
US08/342,558 US5534197A (en) 1994-01-25 1994-11-21 Gemini polyhydroxy fatty acid amides
US08/342,558 1994-11-21
GB9425942.1 1994-12-22
GBGB9425942.1A GB9425942D0 (en) 1994-01-25 1994-12-22 Liquid dishwashing detergent compositions

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6034271A (en) * 1996-03-02 2000-03-07 Huels Aktiengesellschaft Betaine gemini surfactants made from amines
US6156721A (en) * 1996-04-23 2000-12-05 Rwe-Dea Aktiengesellschaft Fuer Mineraloel Und Chemie Use of anionic gemini tensides in formulations for washing, cleaning and body care agents
EP1078978A1 (fr) * 1999-08-24 2001-02-28 Clariant GmbH Mélanges de tensioactifs de N-alkyl polyhydroxyamides et amides alcoxylés d'acides gras
US20210230511A1 (en) * 2020-01-28 2021-07-29 The Procter & Gamble Company Cleaning product
EP3858965A1 (fr) 2020-01-28 2021-08-04 The Procter & Gamble Company Produit de nettoyage

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4255294A (en) * 1975-04-01 1981-03-10 Lever Brothers Fabric softening composition
EP0258500A1 (fr) * 1986-09-02 1988-03-09 Akzo N.V. Compositions adoucissantes pour le linge et détergents les contenant
US5112688A (en) * 1989-02-27 1992-05-12 The Procter & Gamble Company Microcapsules containing hydrophobic liquid core
US5223179A (en) * 1992-03-26 1993-06-29 The Procter & Gamble Company Cleaning compositions with glycerol amides
US5236615A (en) * 1991-08-28 1993-08-17 The Procter & Gamble Company Solid, particulate detergent composition with protected, dryer-activated, water sensitive material

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4255294A (en) * 1975-04-01 1981-03-10 Lever Brothers Fabric softening composition
EP0258500A1 (fr) * 1986-09-02 1988-03-09 Akzo N.V. Compositions adoucissantes pour le linge et détergents les contenant
US5112688A (en) * 1989-02-27 1992-05-12 The Procter & Gamble Company Microcapsules containing hydrophobic liquid core
US5236615A (en) * 1991-08-28 1993-08-17 The Procter & Gamble Company Solid, particulate detergent composition with protected, dryer-activated, water sensitive material
US5223179A (en) * 1992-03-26 1993-06-29 The Procter & Gamble Company Cleaning compositions with glycerol amides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP0741773A4 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6034271A (en) * 1996-03-02 2000-03-07 Huels Aktiengesellschaft Betaine gemini surfactants made from amines
US6156721A (en) * 1996-04-23 2000-12-05 Rwe-Dea Aktiengesellschaft Fuer Mineraloel Und Chemie Use of anionic gemini tensides in formulations for washing, cleaning and body care agents
EP1078978A1 (fr) * 1999-08-24 2001-02-28 Clariant GmbH Mélanges de tensioactifs de N-alkyl polyhydroxyamides et amides alcoxylés d'acides gras
US20210230511A1 (en) * 2020-01-28 2021-07-29 The Procter & Gamble Company Cleaning product
EP3858961A1 (fr) * 2020-01-28 2021-08-04 The Procter & Gamble Company Produit de nettoyage
EP3858965A1 (fr) 2020-01-28 2021-08-04 The Procter & Gamble Company Produit de nettoyage
US11753604B2 (en) 2020-01-28 2023-09-12 The Procter & Gamble Company Cleaning product

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EP0741773A4 (fr) 1998-05-20
CA2179709C (fr) 1999-07-13
CA2179709A1 (fr) 1995-07-27
MX9602985A (es) 1997-03-29

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