GB2234983A - Liquid detergent composition - Google Patents

Liquid detergent composition Download PDF

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Publication number
GB2234983A
GB2234983A GB9015645A GB9015645A GB2234983A GB 2234983 A GB2234983 A GB 2234983A GB 9015645 A GB9015645 A GB 9015645A GB 9015645 A GB9015645 A GB 9015645A GB 2234983 A GB2234983 A GB 2234983A
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weight
group
carbon atoms
formula
alkyl
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GB9015645A
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GB9015645D0 (en
GB2234983B (en
Inventor
Masaki Tosaka
Yutaka Hayakawa
Katsuhiko Deguchi
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Kao Corp
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Kao Corp
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Publication of GB2234983A publication Critical patent/GB2234983A/en
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Publication of GB2234983B publication Critical patent/GB2234983B/en
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    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/86Mixtures of anionic, cationic, and non-ionic compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/22Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29Sulfates of polyoxyalkylene ethers
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/52Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/523Carboxylic alkylolamides, or dialkylolamides, or hydroxycarboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain one hydroxy group per alkyl group
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/662Carbohydrates or derivatives
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/75Amino oxides

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)

Abstract

A detergent composition comprises (a) 10 to 30% by weight of an anionic surfactant having a sulfate group or a sulfonate group, or both; (b) 1 to 10% by weight of a tertamine oxide; (c) 1 to 15% by weight of a fatty acid alkanolamide; and (d) 0.5% to loss than 2.0% by weight of an alkyl glycoside. The detergent compositions exhibit excellent film-forming inhibitory effect and have advantages that the opening of the container cap is not plugged and their qualities do not deteriorate even when used under low humidity for a prolonged period of time.

Description

TITLE OF THE INVENTION LIQUID DETERGENT COMPOSITION BACKGROUND OF THE INVENTION Field of the Invention: This invention relates to a liquid detergent composition, and, more particularly, to a liquid detergent composition exhibiting an excellent film-forming inhibitory effect.
Description of the Background Art: For liquid detergent compositions, e.g. dishwashing detergents, anionic surfactants are generally used as a major detergent component because of their excellent detergency and lathering capability. They are usually used together with amphoteric surfactants and/or nonionic surfactants, such as tert-amine oxides, fatty acid alkanolamide and the like as an auxiliary agent for preventing the hand skin from being chapped.
These detergent compositions, however, have a disadvantage in that when water is evaporated from the solution as the time passes, the concentration of the anionic surfactants in a solution increases, thereby forming a film on the surface of the solution. The film frequently plugs the opening of the cap of the detergent container especially in the dry atmosphere during winter.
In order to resolve these problems, extensive studies have been undertaken, and trials of adding effective ingredients to detergent compositions have been reported.
These ingredients are, for example, polyethylene glycol and a water-soluble inorganic acid (Japanese Patent Laid-open No. 92809/1978), polyoxypropylene polyoxyethylene alkyl ether (Japanese Patent Laid-open No. 34306/1979), polyoxyethylene alkyl ether and magnesium sulfate (Japanese Patent Laid-open No. 110211/1979), lower alkylbenzene sulfonate and benzoate (Japanese Patent Laid-open No.
139792/1985), sulfate of polyoxyalkylene adduct of polyvalent alcohol (Japanese Patent Laid-open No.
89797/1987), water-soluble chitin compound (Japanese Patent Laid-open No. 193999/1988), and the like.
These trials, however, still demand improved filmforming inhibitory effect.
Alkyl glycosides known as saccharide-derived nonionic surfactants have lately attracted great attention because of their excellent lathering capability notwithstanding their nonionic nature. There have been some reports concerning detergent compositions making use of alkyl glycoside. They are, for example, a foaming detergent composition comprising, in addition to an alkyl glycoside (degree of saccharide polymerization: 1.5-10) and an anionic surfactant, 2-10% by weight of fatty acid alkanolamide and/or amine oxide (Japanese Patent Laid-open No.
186429/1983); and a dishwashing liquid detergent having high lathering capability and detergency comprising 2-258 by weight of an alkyl glycoside (degree of saccharide polymerization: 1-1.4), 2-25% by weight of a sulfate- or sulfonate-type anionic surfactant, and 1-15% by weight of fatty acid alkanolamide (Japanese Patent Laid-open No.
74999/1987). In these examples the alkyl glycoside is used for improving lathering capability and detergency, and thus formulated in a great amount. The problem of insufficient film-forming inhibitory effect has not been solved in these compositions.
Development of a detergent composition possessing excellent film-forming inhibitory capability has been desired.
In view of this situation, the present inventors have undertaken extensive studies, and have found that desired detergent compositions exhibiting greatly improved filmforming inhibitory capability could be obtained by adding a small amount of specific alkyl glycoside to a detergent composition comprising a specific anionic surfactant, tertamine oxide, and fatty acid alkanolamide. This finding has led to the completion of this invention.
SUMMARY OF THE INVENTION Accordingly, an object of this invention is to provide a detergent composition comprising: (a) 10 to 30% by weight of an anionic surfactant having a sulfate group or a sulfonate group, or both; (b) 1 to 10% by weight of a tert-amine oxide represented by formula (I):
wherein R1 represents a linear or branched alkyl or alkenyl group having 8-18 carbon atoms, R2 and R3 may be the same or different and represent an alkyl or alkanol group having 1-3 carbon atoms; (c) 1 to 15% by weight of a fatty acid alkanolamide represented by formula (II):
wherein R4 represents a linear or branched alkyl or alkenyl group having 7-19 carbon atoms, a is a value of which the average is 0-5, and b is a value of which the average is 15.
(d) 0.5% to less than 2.0% by weight of an alkyl glycoside represented by formula (III): R5-(OR6)x-(G)Y (III) wherein R5 represents a linear or branched alkyl, alkenyl, or alkylphenyl group having 8-14 carbon atoms, R6 represents an alkylene group having 2-4 carbon atoms, G represents a reducing sugar having 5-6 carbon atoms, x is a value of which the average is 0-5, and y is a value of which the average is 1.0-1.42.
Other objects, features and advantages of the invention will hereinafter become more readily apparent from the following description.
DETAILED DESCRIPTION OF THE INVENTION AND PREFERRED EMBODIMENTS Given as examples of anionic surfactants containing a sulfate group and/or a sulfonate group, which are component (a) of the present invention, are polyoxyethylene alkyl ether sulfate, alkylbenzene sulfonate, a-olefin sulfonate, alkane sulfonate, a-sulfonated fatty acid derivatives, and the like. They are used singly or as a mixture of one or more of them.
Among them, polyoxyethylene alkyl ether sulfates, especially those represented by formula (IV), are preferable from the aspect of mildness to the skin.
R7O (CH2CH2O) nSO3M (IV) wherein R7 represents an alkyl or alkenyl group having 10-18 carbon atoms, M represents an alkali metal, ammonium, or alkanolamine, and n is a value of which the average is 1-7.
A preferable carbon number of R7 is 10-18, particularly 1214, considering detergency and low-temperature stability of a detergent composition. A preferable average addition mol (n) of ethylene oxide in formula (IV) is 1-7, particularly 2-5, considering detergency and irritation to the hand skin.
From the aspect of both detergency and the cost, alkylbenzene sulfonates represented by formula (V) are preferable.
wherein R8 represents an alkyl group having 10-16 carbon atoms and M has the same meaning as previously defined. A preferable carbon number of R8 is 10-16, and, in particular, 11-13.
Component (a) is incorporated as a major component in the detergent composition of the present invention in an amount of 10-30% by weight. The amount of less than 10% by weight results in poor detergency and insufficient lathering capability. If the amount exceeds 30% by weight, the lowtemperature stability of the composition greatly decreases.
Tert-amine oxide, component (b) of the present invention, is defined by formula (I). Among those represented by formula (I), alkyldimethylamine oxides having 12-14 carbon atoms is particularly preferable. 1-10% by weight of component (b) is incorporated in the composition for improving mildness to the skin and reducing the chapping of the hand skin, thus making up for the drawbacks of major component (a), and for increasing detergency and lathering capability. If the amount is less than 1% by weight, these effects are only insufficiently exhibited, while the amount exceeding 10% by weight gives an adverse effect on lowtemperature stability.
Fatty acid alkanolamide, component (c) of the present invention, is represented by the compounds of formula (II).
A preferable carbon number of R4 in formula (II) is 10-14.
Average ethylene oxide addition mol a and b in formula (II) is preferably 0-2 and 1-3, respectively. Component (c) is incorporated in the composition in an amount of 1-15% by weight for the same purpose as of component (b). If the amount is less than 1% by weight, the above effects are suppressed, while an amount exceeding 10% by weight results in unacceptably poor low-temperature stability.
Alkyl glycoside, which is component (d) of this invention and represented by formula (III), contributes to the promotion of film-forming inhibitory capability of the composition when incorporated therein in a certain amount.
A carbon number of R5 in formula (III) must be in a range of 8-14. If the carbon number is out of this range, the effect is remarkably reduced. The preferable carbon number of R5 is 8-12. As R6 which represents an alkylene group of a C24 atom content, ethylene group is preferable. Of the average alkylene oxide addition mol x of 0-5 in formula (III), a preferable range is 0-2. When the value y in formula (III) is larger than 1, i.e., when an alkyl glycoside contains a di- or higher saccharide as the hydrophilic group, the saccharide chain bonds may be 1-2, 1-3, 1-4, 1-6, a- pyranoside, ss-pyranoside, or franoside, or a mixture thereof. Among the value y which is 1.0-1.42, a preferable range is about 1.10-1.40.
The value y is determined by the proton NMR method.
The structure of G in formula (I) depends upon whether the raw material contain a monosaccharide or di- or higher saccharide. Monosaccharides include glucose, galactose, xylose, mannose, lyxose, arabinose, and the like, as well as their mixtures. Examples of di- or higher saccharides are maltose, xylobiose, isomaltose, cellobiose, gentiobiose, lactose, sucrose, nigerose, turanose, raffinose, gentianose, melezitose, and the like, as well as their mixtures. Among these, from the aspect of easy availability and low cost, preferable monosaccharides are glucose and fructose, and preferable di- or higher saccharides are maltose and sucrose.
Component (d) must be incorporated in an amount at least 0.5% by weight and up to 2.0% by weight. If the amount is smaller than 0.5% by weight only the composition imparts only insufficient effects, while at the amount greater than 2.0% by weight the film-forming inhibitory effect is impaired. A particularly preferable range is 1.0-1.8% by weight.
It is desirable that the pH of a neat liquid of the detergent composition of the present invention be adjusted to 4 to 10, particularly preferably to 5 to 8.
Besides the above essential components, the composition of the present invention may comprise other conventionally known surfactants inasmuch as the effect of the present invention is not affected. Such surfactants may include nonionic surfactants, e.g. polyoxyethylene(EO=3-20) alkyl or alkenyl(C7,16, linear or blanched) ether, polyoxyethylene(EO=3-20) alkyl or alkenyl(C7,16, linear or blanched)phenyl ether; amphoteric surfactants, e.g.
alkyl(C8,18) betain, alkyl(C8,18) sulfobetain; and the like.
Besides the above-mentioned components, other components which are generally used in detergent compositions can optionally be used for the detergent composition of the present invention. Such components include, for example, lower alcohols such as ethanol and the like; lower alkylbenzene sulfonates such as p-toluene sulfonate and the like; glycols such as ethylene glycol, propylene glycol, and the like; hydrotropic agents such as urea and the like; pH buffers such as citric acid, malic acid, and the like; organic or inorganic builders; natural juice such as lemon, lime, and the like; hand-chapping protecting agents; enzyme; protein derivatives; pigments; perfumes; turbidity agents; chelating agents; antiseptics; ultraviolet ray absorbers; and the like.
Other features of the invention will become apparent in the course of the following description of the exemplary embodiments which are given for illustration of the invention and are not intended to be limiting thereof.
EXAMPLES Example 1 Detergent compositions listed in Table 1 were prepared.
A film-forming inhibitory effect of each composition was evaluated according to the following method. The results are shown in Table 1.
< Evaluation Method > 50 g of each composition was charged into a 100 ml beaker, and allowed to stand in an air-conditioned room at 200C and 40% humidity for three days. The state of the compositions was then evaluated according to the following standard.
Evaluation standard AAA: No change BBB: A thin film was formed CCC: A steady film was formed TABLE 1 (components: % by weight) Inventive Composition Comparative Composition 1 2 3 4 5 6 7 8 9 Component (a) Sodium polyoxyethylene(3) 20 15 10 10 20 15 10 10 21 dodecyl ether sulfate Sodium linear alkylbenzene- - 15 - 10 - 15 - 10 sulfonate (MW=344) Sodium &alpha;-olefin sulfonate - - 20 - - - 20 - (MW=326) Sodium alkane sulfonate - - - 10 - - - 10 (MW=356) Component (b) Dodecyldimethylamine oxide 2 2 3 3 2 2 3 3 Component (c) Coconut oil fatty acid 5 5 7 7 5 5 7 7 3 diethanolamide Component (d) Alkyl glycoside *1 1 1 1.5 1.8 - 0.1 3 5 1.5 Ethanol 3 3 3 3 3 3 3 3 3 Water Balance Balance Film-forming inhibitory AAA AAA AAA AAA CCC CCC BBB BBB BBB effect * 1 R5:C10, x: 0, G: glucose residue, y: 1.3 in formula (III) Example 2 Detergent compositions shown below were prepared and the film-forming inhibitory effect of each composition was studied. The results are shown in Table 2.
Sodium polyoxyethylene(EO=4) 20.0% by weight dodecyl ether sulfate Dodecyldimethylamine oxide 3.0% Lauric acid diethanolamide 5.0% Alkyl glycoside (see Table 2) 0 or 1.8% Ethanol 3.0% Water Balance Table 2 Alkyl glycoside Film-forming Composition R5(oR6)xGy (III) inhibitory effect R5 R6 x G y Inventive Composition 10 C1OH21 - O Glucose 1.4 AAA 11 CgH19 - O Maltose 1.1 AAA 12 C12H23 CH2CH2 1 Glucose 1.0 AAA 13 C12H23 CH2CH2 2 Glucose 1.3 AAA Comparative Composition 14 C16H31 CH2CH2 3 Glucose 1.4 CCC 15 C12H23 - 0 Glucose 1.7 CCC 16 C1OH21 - 0 Glucose 2.0 CCC 17 Not added CCC The liquid detergent compositions of the present invention exhibit excellent film-forming inhibitory effect and have advantages that an opening of cap is not blocked and their qualities do not deteriorate even when used under low humidity for a prolonged period of time.
Obviously, numerous modifications and variations of the present invention are possible in light of the above teachings. It is therefore to be understood that within the scope of the appended claims, the invention may be practiced otherwise than as specifically described herein.

Claims (2)

WHAT IS CLAIMED IS:
1. A detergent composition comprising: (a) 10 to 30% by weight of an anionic surfactant having a sulfate group or a sulfonate group, or both; (b) 1 to 10% by weight of a tert-amine oxide represented by formula (I):
wherein R1 represents a linear or branched alkyl or alkenyl group having 8-18 carbon atoms, R2 and R3 may be the same or different and represent an alkyl or alkanol group having 1-3 carbon atoms; (c) 1 to 15% by weight of a fatty acid alkanolamide represented by formula (II):
wherein R4 represents a linear or branched alkyl or alkenyl group having 7-19 carbon atoms, a is a value of which the average is 0-5, and b is a value of which the average is 15.
(d) 0.5% to less than 2.0% by weight of an alkyl glycoside represented by formula (III): R5-(OR6 )x(G)y (III) wherein R5 represents a linear or branched alkyl, alkenyl, or alkylphenyl group having 8-14 carbon atoms, R6 represents an alkylene group having 2-4 carbon atoms, G represents a reducing sugar having 5-6 carbon atoms, x is a value of which the average is 0-5, and y is a value of which the average is 1.0-1.42.
2. A detergent composition as claimed in Claim 1 substantially as hereinbefore described in the examples.
GB9015645A 1989-07-25 1990-07-17 Liquid detergent composition Expired - Fee Related GB2234983B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP1191636A JPH0699711B2 (en) 1989-07-25 1989-07-25 Liquid detergent composition

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GB9015645D0 GB9015645D0 (en) 1990-09-05
GB2234983A true GB2234983A (en) 1991-02-20
GB2234983B GB2234983B (en) 1993-01-06

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0509608A2 (en) * 1991-04-15 1992-10-21 Colgate-Palmolive Company Light duty liquid detergent compositions
WO1995020027A1 (en) * 1994-01-25 1995-07-27 The Procter & Gamble Company High sudsing light duty liquid or gel dishwashing detergent compositions containing long chain amine oxide
WO1996001306A1 (en) * 1994-07-05 1996-01-18 The Procter & Gamble Company Handwash laundry detergent composition having improved mildness and cleaning performance
WO1997047717A2 (en) * 1996-06-13 1997-12-18 Colgate-Palmolive Company Light duty liquid cleaning compositions
EP0854182A2 (en) * 1997-01-16 1998-07-22 Robert McBride Ltd Detergent formulation
WO1998046713A1 (en) * 1997-04-16 1998-10-22 Unilever Plc Light duty cleaning composition
CN106831890A (en) * 2017-02-24 2017-06-13 湘潭大学 A kind of Novel wooden polyglycoside surfactants
CN106831900A (en) * 2017-02-24 2017-06-13 湘潭大学 A kind of glucoside compound
US10464965B2 (en) 2011-12-22 2019-11-05 Alios Biopharma, Inc. Substituted nucleosides, nucleotides and analogs thereof
US10485815B2 (en) 2012-03-21 2019-11-26 Alios Biopharma, Inc. Substituted nucleosides, nucleotides and analogs thereof
USRE48171E1 (en) 2012-03-21 2020-08-25 Janssen Biopharma, Inc. Substituted nucleosides, nucleotides and analogs thereof

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EP0070074A2 (en) * 1981-07-13 1983-01-19 THE PROCTER &amp; GAMBLE COMPANY Foaming surfactant compositions
EP0070075A2 (en) * 1981-07-13 1983-01-19 THE PROCTER &amp; GAMBLE COMPANY Foaming dishwashing liquid compositions
EP0070076A2 (en) * 1981-07-13 1983-01-19 THE PROCTER &amp; GAMBLE COMPANY Foaming dishwashing liquid compositions
EP0216301A2 (en) * 1985-09-25 1987-04-01 Henkel Kommanditgesellschaft auf Aktien Liquid cleaning agent
US4663069A (en) * 1982-04-26 1987-05-05 The Procter & Gamble Company Light-duty liquid detergent and shampoo compositions
EP0341071A2 (en) * 1988-05-06 1989-11-08 Unilever Plc Detergent compositions
WO1990002164A1 (en) * 1988-08-19 1990-03-08 Colgate Palmolive Company Light duty liquid detergent compositions

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JPS58186428A (en) * 1982-04-26 1983-10-31 ザ・プロクタ−・エンド・ギヤンブル・カンパニ− Foamable surfactant composition
CA1209010A (en) * 1982-04-26 1986-08-05 Keith A. Jones Foaming surfactant compositions
JPS6289797A (en) * 1985-09-25 1987-04-24 花王株式会社 Liquid detergent composition

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Publication number Priority date Publication date Assignee Title
EP0070074A2 (en) * 1981-07-13 1983-01-19 THE PROCTER &amp; GAMBLE COMPANY Foaming surfactant compositions
EP0070075A2 (en) * 1981-07-13 1983-01-19 THE PROCTER &amp; GAMBLE COMPANY Foaming dishwashing liquid compositions
EP0070076A2 (en) * 1981-07-13 1983-01-19 THE PROCTER &amp; GAMBLE COMPANY Foaming dishwashing liquid compositions
US4663069A (en) * 1982-04-26 1987-05-05 The Procter & Gamble Company Light-duty liquid detergent and shampoo compositions
EP0216301A2 (en) * 1985-09-25 1987-04-01 Henkel Kommanditgesellschaft auf Aktien Liquid cleaning agent
EP0341071A2 (en) * 1988-05-06 1989-11-08 Unilever Plc Detergent compositions
WO1990002164A1 (en) * 1988-08-19 1990-03-08 Colgate Palmolive Company Light duty liquid detergent compositions

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0509608A2 (en) * 1991-04-15 1992-10-21 Colgate-Palmolive Company Light duty liquid detergent compositions
EP0509608A3 (en) * 1991-04-15 1993-03-10 Colgate-Palmolive Company Light duty liquid detergent compositions
GR1001299B (en) * 1991-04-15 1993-07-30 Colgate Palmolive Co Duty liquid detergent composition.
TR25951A (en) * 1991-04-15 1993-11-01 Colgate Palmolive Co LIQUID DETERGENT COMPOSITIONS USED IN LIGHT WORKS
AU661682B2 (en) * 1991-04-15 1995-08-03 Colgate-Palmolive Company, The Light duty liquid detergent compositions
WO1995020027A1 (en) * 1994-01-25 1995-07-27 The Procter & Gamble Company High sudsing light duty liquid or gel dishwashing detergent compositions containing long chain amine oxide
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
WO1996001306A1 (en) * 1994-07-05 1996-01-18 The Procter & Gamble Company Handwash laundry detergent composition having improved mildness and cleaning performance
WO1997047717A2 (en) * 1996-06-13 1997-12-18 Colgate-Palmolive Company Light duty liquid cleaning compositions
WO1997047717A3 (en) * 1996-06-13 1998-01-29 Colgate Palmolive Co Light duty liquid cleaning compositions
EP0854182A2 (en) * 1997-01-16 1998-07-22 Robert McBride Ltd Detergent formulation
EP0854182A3 (en) * 1997-01-16 1998-12-16 Robert McBride Ltd Detergent formulation
WO1998046713A1 (en) * 1997-04-16 1998-10-22 Unilever Plc Light duty cleaning composition
US10464965B2 (en) 2011-12-22 2019-11-05 Alios Biopharma, Inc. Substituted nucleosides, nucleotides and analogs thereof
US11021509B2 (en) 2011-12-22 2021-06-01 Janssen Biopharma, Inc. Substituted nucleosides, nucleotides and analogs thereof
US10485815B2 (en) 2012-03-21 2019-11-26 Alios Biopharma, Inc. Substituted nucleosides, nucleotides and analogs thereof
USRE48171E1 (en) 2012-03-21 2020-08-25 Janssen Biopharma, Inc. Substituted nucleosides, nucleotides and analogs thereof
CN106831890A (en) * 2017-02-24 2017-06-13 湘潭大学 A kind of Novel wooden polyglycoside surfactants
CN106831900A (en) * 2017-02-24 2017-06-13 湘潭大学 A kind of glucoside compound

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Publication number Publication date
JPH0356597A (en) 1991-03-12
GB9015645D0 (en) 1990-09-05
HK107493A (en) 1993-10-22
JPH0699711B2 (en) 1994-12-07
GB2234983B (en) 1993-01-06

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