WO1995003782A1 - Pearlescent based concentrate for personal care products - Google Patents

Pearlescent based concentrate for personal care products Download PDF

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Publication number
WO1995003782A1
WO1995003782A1 PCT/AU1994/000421 AU9400421W WO9503782A1 WO 1995003782 A1 WO1995003782 A1 WO 1995003782A1 AU 9400421 W AU9400421 W AU 9400421W WO 9503782 A1 WO9503782 A1 WO 9503782A1
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WO
WIPO (PCT)
Prior art keywords
group
chosen
formula
pearlescent
alkyl
Prior art date
Application number
PCT/AU1994/000421
Other languages
French (fr)
Inventor
Katherine Margaret Wansborough
Anne Maree Lombard
Pamela Joyce Jones
Original Assignee
Ici Australia Operations Proprietary Limited
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
Application filed by Ici Australia Operations Proprietary Limited filed Critical Ici Australia Operations Proprietary Limited
Priority to KR1019960700426A priority Critical patent/KR960703565A/en
Priority to NZ269755A priority patent/NZ269755A/en
Priority to AU73403/94A priority patent/AU673099B2/en
Publication of WO1995003782A1 publication Critical patent/WO1995003782A1/en

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73Polysaccharides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39Derivatives containing from 2 to 10 oxyalkylene groups
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/463Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60Sugars; Derivatives thereof
    • A61K8/604Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/10Washing or bathing preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair
    • 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
    • C11D1/83Mixtures of non-ionic with anionic 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
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005Other compounding ingredients characterised by their effect
    • C11D3/0089Pearlescent compositions; Opacifying agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59Mixtures
    • A61K2800/596Mixtures of surface active compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/04Carboxylic acids or salts thereof
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/123Sulfonic acids or sulfuric acid esters; Salts thereof derived from carboxylic acids, e.g. sulfosuccinates
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/143Sulfonic acid esters
    • 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
    • C11D1/146Sulfuric acid esters
    • 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
    • C11D1/525Carboxylic 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
    • 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
    • C11D1/72Ethers of polyoxyalkylene glycols
    • 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
    • C11D1/72Ethers of polyoxyalkylene glycols
    • C11D1/721End blocked 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
    • C11D1/66Non-ionic compounds
    • C11D1/74Carboxylates or sulfonates esters of polyoxyalkylene glycols

Definitions

  • the invention relates to pearlescent based concentrates comprising at least one al ylpolysaccharide, traditional pearlescent esters or acid and alkyl sulphates and to processes for the preparation thereof.
  • Personal care products such as handsoaps, bubble baths, shampoos and hair conditioners often include in their composition agents which impart a pleasant, pearl-like glossy appearance in order to enhance the appeal of such products to the consumer.
  • the agents which impart this appearance are known as pearlescent based concentrates and generally comprise microscopic platelike crystals which remain dispersed in compositions to which they are added and reflect light in such a manner as to impart a pearl-like appearance.
  • Pearlescent based concentrates of the prior art have included finely divided natural substances or inorganic compounds such as mica, fish scale, bismuth oxychloride or the like.
  • Japanese patent application no. 90/134,825 (Priority Date; 24 May 1990) describes compositions for cosmetics having a pearly appearance, comprising glucose fatty acid esters and mica and/or mica Ti.
  • a fatty acid glycolic ester in pearlescent concentrates has been particularly favoured.
  • such concentrates are produced by adding a fatty acid glycolic ester which is solid at room temperature to a composition such as shampoo or the like, followed by heating of the mixture to melt the fatty acid glycolic ester, and then by cooling to recrystallise it and thereby providing small crystals which impart a pearl-like gloss to the composition.
  • a pearling agent dispersion such as a fatty acid glycolic ester dispersion, which is dissolved and cooled to recrystallise in advance
  • Other known pearlescent based concentrates have comprised microcrystalline polyvalent metal salts of higher fatty acids or fatty acid glycolic esters such as those described in United States Patent 4,959,200 (Date of Patent; 25 September 1990).
  • pearlescent based concentrates have been prepared using ethylene glycol monostearate, ethylene glycol di-stearate, glycerol monostearate, glycerol di- stearate or a cetyl stearly alcohol or the like in conjunction with other similar esters.
  • These pearlescent based concentrates of the prior art have also normally comprised ether sulphates, betaines, ethanolamide, amine based surfactants and the like which can be used as emulsifiers.
  • United States Patent 5,017,305 (Date of Patent; 21 May 1991) describes a typical pearlescent concentrate in the form of a free-flowing dispersion comprising pearlescing esters, ether carboxylic acids and one or more monoethanolamides of C 12 to C 22 fatty acids.
  • alkyl polyglucosides demonstrate very little tendency to scalp irritations.
  • alkylpolysaccharides are particularly attractive for use in personal care products because they contain no toxic trace impurities and because they are derived from renewable resources such as coconut oil and wheat starch.
  • the current invention therefore provides a pearlescent based concentrate including: between 5 and 40% by weight of the composition of alkylpolysaccharide of formula
  • R is selected from the group comprising linear or branched C 6 to C 22 alkyl or alkenyl group where G is selected from the group comprising a C 5 or C 6 saccharide and x is from 1 to 10;
  • R2 -(°C n H 2n ) ⁇ -OR 3 where R is chosen from the group including C 16 to C 22 fatty acyl groups, R 3 is chosen from the group comprising H or R2, n is 2 or 3 and x is from 1 to 120.
  • the current invention further provides a pearlescent based concentrate including: H-G ⁇ -0R 1 where R is selected from the group comprising linear or branched C 6 to C 22 alkyl or alkenyl group where G is selected from the group comprising a C 5 or C 6 saccharide and x is from 1 to 10; between 3 and 30% by weight of the composition of alkyl sulphate and/or alkyl ether sulphate; and between 5 to 20% by weight of pearlescing acid of formula R COOH where R is chosen from the group comprising C 16 to C 22 alkyl groups.
  • the pearlescing esters or acid of the current invention is chosen from ethylene glycol monostearate, ethylene glycol disterate, stearic acid and mixtures thereof.
  • R 4 CH(CH 3 )S0 3 M where R 4 is chosen from the group comprising
  • C 6 to C 22 alkyl groups and M is chosen from the group comprising alkali metals
  • R 5 (OC 2 H 4 ) y OH where R 5 is chosen from the group including
  • the pearlescent based concentrate of the current invention may further include between 0 and 30% by weight of the composition of one or more optional additives chosen from the group including: alkylsulphosuccinate or polyoxyalkylenealkylsulphosuccinate of the formula
  • R 6 -0-[CH(R 7 )CH 2 0] n -[COCH(S0 3 M)CH 2 COOM 1 ] where R is chosen from the group including C 8 to C 20 linear or branched alkyl groups, R 7 is H or CH 3 ,
  • M and M are independently chosen from the group comprising alkali metals, alkaline earth metals, NH 4 + , C ⁇ to C 3 alkyl groups, substituted ammonia and hydroxy substituted C 2 or C 3 alkyl substituted ammonia and n is from 0 to 8; sorbitan fatty acid esters of formula,
  • R is chosen from the group including C 12 to C 18 ; secondary alkane sulphonates; fatty alcohol alkoxylates; fatty acid alkoxylates; fatty alcohols; alkanoyl N- methylglucamides; ether carboxylic acids; ethoxylated sorbitan fatty acid esters; and alpha-olefin sulphonates.
  • R 9 OH where R is chosen from the group comprising
  • the optional additives of the pearlescent concentrate of the current invention includes alkanoyl N-methylglucamides of the formula COR 10
  • the optional additives of the pearlescent concentrate of the current invention includes ether carboxylic acids of the formula R u C(0)0(C 2 H 4 0) ⁇ H where R is chosen from the group includes C 6 to C 22 alkyl groups and m is from 1 to 120
  • R is chosen from the group comprising
  • R 13 CH CHCH 2 S0 3 M 2 where R is chosen from the group comprising C 6 to C 22 alkyl groups and M is chosen from the group comprising Na & K.
  • Another optional additive to the pearlescent based concentrates of the current invention is between 0 and 2% of at least one inorganic salt including alkali metal halide salt such as NaCl, KCl, Kl and the like.
  • the pearlescent based concentrates of the current invention may also be diluted with between 10 and 90% of the weight of the composition of water or other suitable solvent.
  • the pearlescent based concentrates of the current invention may also have added optional agents including perfumes, pigments, UV absorbers and antioxidants.
  • the pearlescent based concentrates of the current invention may also be prepared by a method comprising the following steps;
  • a pearlescent based concentrate of the following composition was prepared by the method described below.
  • Component Composition (% w/w)
  • Decylpolysaccharide (50% a.i.) 36.00 Sodium lauryl sulphate (30% a.i, 10.00 Ethylene Glycol mono-stearate 16.25 Sodium chloride 1.00 Water 36.75
  • Ethylene glycol monostearate, decylpolysaccharide, alkyl sulphate, water and sodium chloride were heated to 80°C with vigorous stirring. The solution was maintained at 80°C with stirring for further 30 minutes before being rapidly cooled to 65°C. Once the solution temperature reached 65°C the stirring rate was slowed and the solution cooled at a controlled rate of 10°C per hour until the temperature reached 40°C. The stirrer was then stopped and the pearlescent blend allowed to cool to room temperature.
  • a pearlescent based concentrate of the following composition was prepared by the method described below.
  • Component Com osition (% w/w)
  • Ethylene glycol mono-stearate, dodecylpolysaccharide, sodium lauryl sulphate, TERIC 12A23 water and sodium chloride were heated to 80°C with vigorous stirring. Once the solution had reached 80°C, the stirring rate was slowed and the solution cooled at a controlled rate of 10°C per hour until the solution temperature had dropped to 0°C. When the solution temperature had reached 40°C the stirrer was stopped and the pearlescent based composition was allowed to cool to room temperature. (TERIC is a registered trade mark of ICI Australia Operations Proprietary Limited) .
  • Component Composition (%w/w)
  • Ethylene glycol monostearate, decylpolysaccharide, sodium lauryl sulphate, cetyl-stearyl alcohol and water were heated to 75°C with vigorous stirring. The solution was cooled until the temperature reached 70°C at which point the rate of cooling was controlled at 15°C/hour and the stirring rate reduced. When temperature reached 40°C, stirring was stopped and the pearlescent based composition allowed to cool to room temperature.
  • Component Composition (%w/w)
  • Component Composition (%w/w)
  • the sodium chloride was dissolved in a portion of the water. The remaining components were blended together and the salt solution mixed in. The resultant mixture was heated to 70°C with rapid stirring then the stirring rate was reduced and the mixture cooled at a rate of 8°C per hour. When the mixture reached 40°C all stirring was ceased.
  • Component Composition (%w/w)
  • Example 5 The above components were combined according to the method of Example 5 to form a pearlescent based concentrate.
  • Component Composition ( %w/w) C8-10 Polysaccharide 5 . 00 Decyl Polysaccharide 25 . 00 Sodium lauryl sulphate 20 . 00 Ethylene glycol monostearate 15 . 00 Sodium Chloride 1 . 00 Water 34 . 00 Method
  • Example 5 The above components were combined according to the method of Example 5 to form a pearlescent based concentrate
  • Component Composition (%w/w)
  • Example 5 The above components were combined according to the method of Example 5 to form a pearlescent based concentrate.
  • Component Composition (%w/w)
  • Example 5 The above components were combined according to the method of Example 5 to form a pearlescent based concentrate
  • Example 5 The above components were combined according to the method of Example 5 to form a pearlescent based concentrate,
  • the pearlescent based concentrates of each example exhibited small crystals of relatively uniform size which give a lustrous appearance to the concentrate and good reflectance.

Abstract

A pearlescent based concentrate and method of preparation wherein the concentrate comprises at least one alkylpolysaccharide, traditional pearlscent ester or acid and alkyl sulphates. The concentrate is suitable for use in personal care products of low irritancy to the skin of users.

Description

PEARLESCENT BASED CONCENTRATE FOR PERSONAL CARE PRODUCTS
The invention relates to pearlescent based concentrates comprising at least one al ylpolysaccharide, traditional pearlescent esters or acid and alkyl sulphates and to processes for the preparation thereof.
Personal care products such as handsoaps, bubble baths, shampoos and hair conditioners often include in their composition agents which impart a pleasant, pearl-like glossy appearance in order to enhance the appeal of such products to the consumer. The agents which impart this appearance are known as pearlescent based concentrates and generally comprise microscopic platelike crystals which remain dispersed in compositions to which they are added and reflect light in such a manner as to impart a pearl-like appearance.
Pearlescent based concentrates of the prior art have included finely divided natural substances or inorganic compounds such as mica, fish scale, bismuth oxychloride or the like. For example, Japanese patent application no. 90/134,825 (Priority Date; 24 May 1990) describes compositions for cosmetics having a pearly appearance, comprising glucose fatty acid esters and mica and/or mica Ti.
In recent years, the use of a fatty acid glycolic ester in pearlescent concentrates has been particularly favoured. In general such concentrates are produced by adding a fatty acid glycolic ester which is solid at room temperature to a composition such as shampoo or the like, followed by heating of the mixture to melt the fatty acid glycolic ester, and then by cooling to recrystallise it and thereby providing small crystals which impart a pearl-like gloss to the composition. In an alternative method of production, a pearling agent dispersion (such as a fatty acid glycolic ester dispersion, which is dissolved and cooled to recrystallise in advance) is mixed with a shampoo or the like at room temperature as described in Japanese Patent Application nos. 71021/81 and 216728/83. Other known pearlescent based concentrates have comprised microcrystalline polyvalent metal salts of higher fatty acids or fatty acid glycolic esters such as those described in United States Patent 4,959,200 (Date of Patent; 25 September 1990).
Other commonly used pearlescent based concentrates have been prepared using ethylene glycol monostearate, ethylene glycol di-stearate, glycerol monostearate, glycerol di- stearate or a cetyl stearly alcohol or the like in conjunction with other similar esters. These pearlescent based concentrates of the prior art have also normally comprised ether sulphates, betaines, ethanolamide, amine based surfactants and the like which can be used as emulsifiers. United States Patent 5,017,305 (Date of Patent; 21 May 1991) describes a typical pearlescent concentrate in the form of a free-flowing dispersion comprising pearlescing esters, ether carboxylic acids and one or more monoethanolamides of C12 to C22 fatty acids.
One of the disadvantages of the pearlescent based concentrates of the prior art is that they often comprise chemicals which are potential skin sensitisers. Japanese Patent Application no. 21678/83 for example, discloses a pearling agent containing a salt of alkyl sulphate or a salt of polyoxyalkylene alkyl sulphate, a fatty acid dialkanolamide and water as solvents, and a fatty acid glycolic ester at a high concentration. Many factors influence the irritation effect of surfactants and the molecular structure of the surface active agent can be closely linked to its effect on adsorption, solubilization, penetration, swelling, denaturation and general irritation o human skin.
Generally, the order of increasing human skin irritatio of anionic surfactants commonly used in personal care products is in the following order: Ammonium Laureth Sulphate <Sodium Laureth Sulphate <Ammonium Lauryl Sulphate <Sodium Lauryl Sulphate. Furthermore, some of the pearlescent based concentrates of the prior art have included surfactants which may contain toxic trace impurities which are suspected carcinogens including nitrosamine containing compounds such as diethanolamides. European Patent no. 221465 (22 October
1992) for example, relates to a process for the production of pearlescent pigment comprising ethanolamide.
In general, alkyl polyglucosides demonstrate very little tendency to scalp irritations.
It has now been found that low irritant pearlescent based concentrates containing biodegradable surfactants can be prepared using alkylpolysaccharides. Ultimate biodegradability was measured using OECD tests 301E and 301A,1981. Alkylpolysaccharides are particularly attractive for use in personal care products because they contain no toxic trace impurities and because they are derived from renewable resources such as coconut oil and wheat starch.
The current invention therefore provides a pearlescent based concentrate including: between 5 and 40% by weight of the composition of alkylpolysaccharide of formula
H-Gχ-OR1 where R is selected from the group comprising linear or branched C6 to C22 alkyl or alkenyl group where G is selected from the group comprising a C5 or C6 saccharide and x is from 1 to 10;
between 3 and 30% by weight of the composition of alkyl sulphate and/or alkyl ether sulphate; and between 5 and 20% by weight of pearlescing esters of formula
R2-(°CnH2n)χ-OR3 where R is chosen from the group including C16 to C22 fatty acyl groups, R 3 is chosen from the group comprising H or R2, n is 2 or 3 and x is from 1 to 120.
The current invention further provides a pearlescent based concentrate including: H-Gχ-0R1 where R is selected from the group comprising linear or branched C6 to C22 alkyl or alkenyl group where G is selected from the group comprising a C5 or C6 saccharide and x is from 1 to 10; between 3 and 30% by weight of the composition of alkyl sulphate and/or alkyl ether sulphate; and between 5 to 20% by weight of pearlescing acid of formula R COOH where R is chosen from the group comprising C16 to C22 alkyl groups.
In a preferred embodiment the pearlescing esters or acid of the current invention is chosen from ethylene glycol monostearate, ethylene glycol disterate, stearic acid and mixtures thereof.
In a preferred embodiment the pearlescent based concentrate of the current invention further includes secondary alkane sulphonates of the formula
R4 - CH(CH3)S03M where R4 is chosen from the group comprising
C6 to C22 alkyl groups and M is chosen from the group comprising alkali metals
In a further preferred embodiment the fatty alcohol ethoxylates used in pearlescent based concentrate of the current invention are of the formula
R5 (OC2H4)y OH where R5 is chosen from the group including
C6 and C22 alkyl or alkenyl groups and y is from 1 to 120 The pearlescent based concentrate of the current invention may further include between 0 and 30% by weight of the composition of one or more optional additives chosen from the group including: alkylsulphosuccinate or polyoxyalkylenealkylsulphosuccinate of the formula
R6-0-[CH(R7)CH20]n-[COCH(S03M)CH2COOM1] where R is chosen from the group including C8 to C20 linear or branched alkyl groups, R7 is H or CH3,
M and M are independently chosen from the group comprising alkali metals, alkaline earth metals, NH4 +, Cχ to C3 alkyl groups, substituted ammonia and hydroxy substituted C2 or C3 alkyl substituted ammonia and n is from 0 to 8; sorbitan fatty acid esters of formula,
CH2-(CHOH)3-CHOCH2OR8 where R is chosen from the group including C12 to C18; secondary alkane sulphonates; fatty alcohol alkoxylates; fatty acid alkoxylates; fatty alcohols; alkanoyl N- methylglucamides; ether carboxylic acids; ethoxylated sorbitan fatty acid esters; and alpha-olefin sulphonates.
In a preferred embodiment the optional additives of the pearlescent concentrate of the current invention includes fatty alcohols of the formula
R9OH where R is chosen from the group comprising
C6 to C22 alkyl groups
In a further preferred embodiment the optional additives of the pearlescent concentrate of the current invention includes alkanoyl N-methylglucamides of the formula COR10
CH3-N-CH2(CHOH)4CH2OH where RR1100 is chosen from the group comprising C6 and C22 alkyl groups In another preferred embodiment the optional additives of the pearlescent concentrate of the current invention includes ether carboxylic acids of the formula RuC(0)0(C2H40)πιH where R is chosen from the group includes C6 to C22 alkyl groups and m is from 1 to 120
In a further preferred embodiment the optional additives of the pearlescent concentrate of the current invention comprise ethoxylated sorbitan fatty acid esters of the formula
Figure imgf000008_0001
where R is chosen from the group comprising
C6 to C22 alkyl groups and w, v, u, t are from 4 to 20
In a further preferred embodiment the optional additives of the pearlescent concentrate of the current invention comprise alpha-olefin sulphonates of formula
R13CH = CHCH2S03M2 where R is chosen from the group comprising C6 to C22 alkyl groups and M is chosen from the group comprising Na & K.
Another optional additive to the pearlescent based concentrates of the current invention is between 0 and 2% of at least one inorganic salt including alkali metal halide salt such as NaCl, KCl, Kl and the like.
The pearlescent based concentrates of the current invention may also be diluted with between 10 and 90% of the weight of the composition of water or other suitable solvent. The pearlescent based concentrates of the current invention may also have added optional agents including perfumes, pigments, UV absorbers and antioxidants.
There is further provided a method of preparation of the pearlescent based concentrates of the current invention comprising the steps of;
(a) heating the components to a temperature above the highest melting point of the components but less than the boiling point of any solvents present and stirring to form a homogeneous solution, and
(b) cooling the stirring solution to a temperature of between 35°C and 45°C at a maximum cooling rate of 15°C/hour.
The pearlescent based concentrates of the current invention may also be prepared by a method comprising the following steps;
(a) heating the components to a temperature above the highest melting point of the components but less than the boiling point of any solvents present while stirring vigorously to form a homogeneous solution,
(b) rapidly cooling the stirring solution to between 60°C and 70°C, and
(c) cooling the stirring solution to a temperature of between 35°C and 45°C at a maximum cooling rate of 15°C/hour.
The current invention will now be described with reference to the following non-limiting examples; EXAMPLE 1
A pearlescent based concentrate of the following composition was prepared by the method described below.
Component Composition (% w/w)
Decylpolysaccharide (50% a.i.) 36.00 Sodium lauryl sulphate (30% a.i, 10.00 Ethylene Glycol mono-stearate 16.25 Sodium chloride 1.00 Water 36.75
Method
Ethylene glycol monostearate, decylpolysaccharide, alkyl sulphate, water and sodium chloride were heated to 80°C with vigorous stirring. The solution was maintained at 80°C with stirring for further 30 minutes before being rapidly cooled to 65°C. Once the solution temperature reached 65°C the stirring rate was slowed and the solution cooled at a controlled rate of 10°C per hour until the temperature reached 40°C. The stirrer was then stopped and the pearlescent blend allowed to cool to room temperature.
EXAMPLE 2
A pearlescent based concentrate of the following composition was prepared by the method described below.
Component Com osition (% w/w)
Dodecylpolysaccharide (50% a.i.) Sodium lauryl sulphate (30% a.i.) TERIC 12A23
Ethylene glycol mono-stearate Sodium chloride Water
Figure imgf000010_0001
Method
Ethylene glycol mono-stearate, dodecylpolysaccharide, sodium lauryl sulphate, TERIC 12A23 water and sodium chloride were heated to 80°C with vigorous stirring. Once the solution had reached 80°C, the stirring rate was slowed and the solution cooled at a controlled rate of 10°C per hour until the solution temperature had dropped to 0°C. When the solution temperature had reached 40°C the stirrer was stopped and the pearlescent based composition was allowed to cool to room temperature. (TERIC is a registered trade mark of ICI Australia Operations Proprietary Limited) .
EXAMPLE 3
Component Composition (%w/w)
Decylpolysaccharide (50% a.i.) 37.00
Sodium lauryl sulphate 10.00
Cetyl Stearyl alcohol 5.00
Ethylene glycol monostearate 16.25 Water 32.75
Method
Ethylene glycol monostearate, decylpolysaccharide, sodium lauryl sulphate, cetyl-stearyl alcohol and water were heated to 75°C with vigorous stirring. The solution was cooled until the temperature reached 70°C at which point the rate of cooling was controlled at 15°C/hour and the stirring rate reduced. When temperature reached 40°C, stirring was stopped and the pearlescent based composition allowed to cool to room temperature.
EXAMPLE 4
Component Composition (%w/w)
Dodecylpolysaccharide (50% a.i.) 36.00
Ammonium lauryl sulphate (25% a.i.) 10.00 Disodium alkyl ethoxy sulphosuccinate (30% a.i.) 13.3
Sodium chloride 1.0
Ethylene glycol distearate 16.25
Water 23.45
Method Dodecylpolysaccharide, ammonium lauryl sulphate, disodium alkylethoxy sulphosuccinate and ethylene glycoldistearate were blended together to form a homogeneous mixture. Sodium chloride was then dissolved in the water and added to the mixture which was heated to 70°C with vigorous stirring. When the solution temperature reached 70°C the stirring rate was reduced and the solution cooled at a rate of 8°C/hr. When the solution temperature reached 40°C the stirring was stopped and the resultant pearlescent based concentrate left to cool to room temperature.
EXAMPLE 5
Component Composition (%w/w)
Decyl Polysaccharide 25.00 Sodium lauryl sulphate 20.00 Ethylene glycol monostearate 7.50 Sodium Chloride 1.00 Water 46.5
Method
The sodium chloride was dissolved in a portion of the water. The remaining components were blended together and the salt solution mixed in. The resultant mixture was heated to 70°C with rapid stirring then the stirring rate was reduced and the mixture cooled at a rate of 8°C per hour. When the mixture reached 40°C all stirring was ceased.
EXAMPLE 6
Component Composition (%w/w)
Decyl Polysaccharide 25.00 Sodium lauryl sulphate 20.00 Sorbitan monolaurate 5.00 Ethylene glycol monostearate 15.00 Sodium Chloride 1.00 Water 34.00
Method
The above components were combined according to the method of Example 5 to form a pearlescent based concentrate.
EXAMPLE 7
Component Composition ( %w/w) C8-10 Polysaccharide 5 . 00 Decyl Polysaccharide 25 . 00 Sodium lauryl sulphate 20 . 00 Ethylene glycol monostearate 15 . 00 Sodium Chloride 1 . 00 Water 34 . 00 Method
The above components were combined according to the method of Example 5 to form a pearlescent based concentrate,
EXAMPLE 8
Component Composition (%w/w)
Decyl Polysaccharide Ammonium lauryl sulphate Ethoxylated sorbitan monooleate Sodium Chloride Ethylene glycol monostearate Water
Figure imgf000013_0001
Method
The above components were combined according to the method of Example 5 to form a pearlescent based concentrate.
EXAMPLE 9
Component Composition (%w/w)
Decyl Polysaccharide 30.00
Sodium lauryl sulphate 15.00
Stearic acid 15.00 Sodium Chloride 1.00
Water 39.00
Method
The above components were combined according to the method of Example 5 to form a pearlescent based concentrate,
EXAMPLE 10
Component om osition (%w/w)
C16-18 Polysaccharide Decyl Polysaccharide Sodium lauryl sulphate Ethylene glycol monostearate Sodium Chloride Water
Figure imgf000013_0002
Method
The above components were combined according to the method of Example 5 to form a pearlescent based concentrate, The pearlescent based concentrates of each example exhibited small crystals of relatively uniform size which give a lustrous appearance to the concentrate and good reflectance.
While the invention had been explained in relation to its preferred embodiments it is to be understood that various modifications thereof will become apparent to those skilled in the art upon reading the specification. Therefore, it is to be understood that the invention disclosed herein is intended to cover such modifications as fall within the scope of the appended claims.

Claims

The claims defining the inventions are as follows:
1. A pearlescent based concentrate comprising: between 5 and 40% by weight of the composition of alkylpolysaccharide of formula H-G^-OR1 where R is selected from the group comprising linear or branched C6 to C22 alkyl or alkenyl group where G is selected from the group comprising a C5 or C6 saccharide and x is from 1 to 10;
between 3 and 30% by weight of the composition of alkyl sulphate and/or alkyl ether sulphate;
and between 5 and 20% by weight of pearlescing compound of formula R2-(OCnH2n)χ-OR3 where R is chosen from the group including C16 to C22 fatty acyl groups,
R 3 is chosen from the group comprising H or R2, n is 2 or 3 and x is from 0 to 120.
2. A pearlescent based concentrate according to claim 1 comprising: between 5 and 40% by weight of the composition of alkylpolysaccharide of formula H-Gχ-0R1 where R is selected from the group comprising linear or branched C6 to C22 alkyl or alkenyl group where G is selected from the group comprising a C5 or C6 saccharide and x is from 1 to 10;
between 3 and 30% by weight of the composition of alkyl sulphate and/or alkyl ether sulphate; and between 5 and 20% by weight of pearlescing acid of formula
R COOH where R is chosen from the group including C16 to C22 alkyl groups,
3. A pearlescent based concentrate comprising: between 5 and 40% by weight of the composition of alkylpolysaccharide of formula
H-Gχ-OR1 where R is selected from the group comprising linear or branched C6 to C22 alkyl or alkenyl group where G is selected from the group comprising a C5 or C6 saccharide and x is from 1 to 10; between 3 and 30% by weight of the composition of alkyl sulphate and/or alkyl ether sulphate; and between 5 and 20% by weight of pearlescing esters of formula
R2-(°CnH2n)χ-OR3 where R is chosen from the group including C16 to C22 fatty acyl groups,
R is chosen from the group comprising H or R , n is 2 or 3 and x is from 1 to 120.
4. A pearlescent based concentrate according to claim 3 which further includes secondary alkane sulphonates of the formula
R4-CH(CH3)S03M where R is chosen from the group comprising C6 to C22 alkyl groups and M is chosen from the group comprising alkali salts.
5. A pearlescent based concentrates according to claim 3 wherein said fatty alcohol ethoxylate is of formula R5(OC2H4)y OH where R5 is chosen form the group including
C6 and C22 alkyl or alkenyl groups and y is from 1 to 120 .
6. A pearlescent based concentrate according to claim 3 which further includes between 0 and 30% by weight of the composition of one or more optional additives chosen from the group including: alkylsulphosuccinate or polyoxyalkylenealkylsulphosuccinate of the formula
R6-0-[CH(R7)CH20]n-[COCH(S03M)CH2COOM1] where R is chosen from the group including C8 to C20 linear o branched alkyl groups,
R7 is H or CH3, M and M are independently chosen from the group comprising alkali metals, alkaline earth metals, NH4 +, C2 to C3 alkyl groups, substituted ammonia and hydroxy substituted C2 or C3 alkyl substituted ammonia and n is from 0 to 8; sorbitan fatty acid esters of formula,
CH2-(CHOH)3-CHOCH2OR8 where R is chosen from the group including C12 to C18 alkyl group; secondary alkane sulphonates; fatty alcohol alkoxylates; fatty acid alkoxylates; fatty alcohols; alkanoyl N- methylgluca ides; ether carboxylic acids; ethoxylated sorbitan fatty acid esters; and alpha-olefin sulphonates.
7. A pearlescent based concentrate according to claim 3 which further includes fatty alcohols of the formula
R9OH where R9 is chosen from the group comprising
C6 to C22 alkyl groups.
8. A pearlescent based concentrate according to claim 3 which further includes alkanoyl N-methylglucamides of the formula
COR10 I CH3-N-CH2(CHOH)4CH2OH where R10 is chosen from the group consisting C6 and C22 alkyl groups.
9. A pearlescent based concentrate according to claim 3 which further includes ether carboxylic acids of the formula
RnC(0)0(C2H40)mH where R is chosen from the group including C6 to C22 alkyl groups and m is from 1 to 120.
10. A pearlescent based concentrate according to claim 3 which further includes ethoxylated sorbitan fatty acid esters of the formula
Figure imgf000018_0001
where R is chosen from the group comprising C6 to C22 alkyl groups and w, v, u, t are from 4 to 20
11. A pearlescent based concentrate according to claim 3 which further includes alpha-olefin sulphonates of formula
R13CH = CHCH2S03M2 where R is chosen from the group comprising C6 to C22 alkyl groups and M is chosen from the group comprising Na & K.
12. A pearlescent based concentrate according to claim 3 comprising between 0 and 2% of the weight of the composition of inorganic salt.
13. A pearlescent based concentrate according to claim 12 wherein said inorganic salt is an alkali metal halide salt.
14. A pearlescent based concentrate according to claim 3 comprising between 10 and 90% of the weight of the composition of solvent.
15. A pearlescent composition comprising a pearlescent based concentrate according to any of the previous claims and at least one solvent in the ratio of between 10:90 and 90:10 weight %.
16. A pearlescent based concentrate according to claim 1 or 2 which further includes secondary alkane sulphonates of the formula
R4-CH(CH3)S03M where R is chosen from the group comprising C6 to C22 alkyl groups and M is chosen from the group comprising alkali salts.
17. A pearlescent based concentrates according to claim 1 or 2 wherein said fatty alcohol ethoxylate is of formula
R5(OC2H4)y OH where R is chosen form the group including C6 and C22 alkyl or alkenyl groups and y is from 1 to 120.
18. A pearlescent based concentrate according to claim 1 or 2 which further includes between 0 and 30% by weight of the composition of one or more optional additives chosen from the group including: alkylsulphosuccinate or polyoxyalkylenealkylsulphosuccinate of the formula
R6-0-[CH(R7)CH20]n-[COCH(S03M)CH2COOM1] where R is chosen from the group including C8 to C20 linear or branched alkyl groups,
R7 is H or CH3, M and M1 are independently chosen from the group comprising alkali metals, alkaline earth metals, NH4 +, C. to C3 alkyl groups, substituted ammonia and hydroxy substituted C2 or C3 alkyl substituted ammonia and n is from 0 to 8; sorbitan fatty acid esters of formula, CH2-(CHOH)3-CHOCH2OR8 where R8 is chosen from the group including C12 to C18 alkyl group; secondary alkane sulphonates; fatty alcohol alkoxylates; fatty acid alkoxylates; fatty alcohols; alkanoyl N- methylglucamides; ether carboxylic acids; ethoxylated sorbitan fatty acid esters; and alpha-olefin sulphonates.
19. A pearlescent based concentrate according to claim 1 or 2 which further includes fatty alcohols of the formula
R9OH where R is chosen from the group comprising C6 to C22 alkyl groups.
20. A pearlescent based concentrate according to claim 1 or 2 which further includes alkanoyl N-methylglucamides of the formula
COR10
CH3-N-CH2 ( CHOH ) 4CH2OH where R is chosen from tI- VhΪΩe rgττr-(o-mupτι rcnonnscii' csttii nnπg CC '6 . 6 a. "n... . . 1 ,d* "C2222 alkyl groups.
21. A pearlescent based concentrate according to claim 1 or 2 which further includes ether carboxylic acids of the formula
R"C(0)0(C2H40)BH where R is chosen from the group including C6 to C22 alkyl groups and m is from 1 to 120.
22. A pearlescent based concentrate according to claim 1 or 2 which further includes ethoxylated sorbitan fatty acid esters of the formula
Figure imgf000020_0001
where R is chosen from the group comprising
C6 to C22 alkyl groups and w, v, u , t are from 4 to 20
23. A pearlescent based concentrate according to claim 3 which further includes alpha-olefin sulphonates of formula
R13CH = CHCH2S03M2 where R is chosen from the group comprising C6 to C22 alkyl groups and M is chosen from the group comprising Na & K.
24. A method of preparing a pearlescent based concentrates of any of claims 3 to 15 comprising the steps of;
(a) heating the components to a temperature above the highest melting point of the components but less than the boiling point of any solvents present and stirring to form a homogeneous solution, and
(b) cooling the stirring solution to a temperature of between 35°C and 45°C at a maximum cooling rate of 15°C/hour.
25. A method of preparing a pearlescent based concentrates of any of claims 3 to 15 comprising the steps of;
(a) heating the components to a temperature above the highest melting point of the components but less than the boiling point of any solvents present while stirring vigorously to form a homogeneous solution,
(b) rapidly cooling the stirring solution to between 60°C an 70°C, and
(c) cooling the stirring solution to a temperature of between 35°C and 45°C at a maximum cooling rate of
15°C/hour.
26. A method of preparing a pearlescent based concentrates of any of claims 1, 2 or 16 to 23 comprising the steps of;
(a) heating the components to a temperature above the highest melting point of the components but less than the boiling point of any solvents present and stirring to form a homogeneous solution, and
(b) cooling the stirring solution to a temperature of between 35°C and 45°C at a maximum cooling rate of 15°C/hour.
27. A method of preparing a pearlescent based concentrates of any of claims 1, 2 or 16 to 23 comprising the steps of;
(a) heating the components to a temperature above the highest melting point of the components but less than the boiling point of any solvents present while stirring vigorously to form a homogeneous solution,
(b) rapidly cooling the stirring solution to between 60°C and 70°C, and
(c) cooling the stirring solution to a temperature of between 35°C and 45°C at a maximum cooling rate of
15°C/hour.
28. A pearlescent based concentrate substantially as herein described with reference to the examples.
29. A method of preparing a pearlescent based concentrate as herein described with reference to the examples.
PCT/AU1994/000421 1993-07-28 1994-07-26 Pearlescent based concentrate for personal care products WO1995003782A1 (en)

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KR1019960700426A KR960703565A (en) 1993-07-28 1994-07-26 PEARLESCENT BASED CONCENTRATE FOR PERSONAL CARE PRODUCTS
NZ269755A NZ269755A (en) 1993-07-28 1994-07-26 Pearlescent based concentrate comprising a pearlescent ester or acid, an alkylpolysaccharide and alkyl sulphates
AU73403/94A AU673099B2 (en) 1993-07-28 1994-07-26 Pearlescent based concentrate for personal care products

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WO1997005224A1 (en) * 1995-07-25 1997-02-13 Henkel Kommanditgesellschaft Auf Aktien Pourable nacreous lustre concentrate
EP0828807A1 (en) * 1995-05-27 1998-03-18 The Procter & Gamble Company Cleansing composition containing polyhydroxy fatty acid amide surfactants
DE19646882A1 (en) * 1996-11-13 1998-05-28 Henkel Kgaa Aqueous pearlescent concentrates
WO1998036048A1 (en) * 1997-02-15 1998-08-20 Henkel Kommanditgesellschaft Auf Aktien Method for producing surfactant pearly luster concentrates
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WO2001025378A2 (en) * 1999-10-07 2001-04-12 Rhodia Consumer Specialties Limited Trading As Albright & Wilson Surfactants Europe Structered surfactant systems containing pearlisers
US6306916B1 (en) 1995-03-29 2001-10-23 Henkel Kommanditgesellschaft Auf Aktien Pearly luster concentrate with newtonian viscosity
WO2003066796A1 (en) * 2002-02-09 2003-08-14 Huntsman International Llc Opacifiers
FR2929856A1 (en) * 2008-04-15 2009-10-16 Rhodia Operations Sas PROCESS FOR THE PREPARATION OF CRYSTALS BASED ON A FATTY ACID ESTER
EP1132079B2 (en) 2000-01-21 2010-05-05 L'oreal Washing composition for keratinic materials comprising a low-ethoxylated sorbitan ester
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WO1996002620A1 (en) * 1994-07-19 1996-02-01 Henkel Kommanditgesellschaft Auf Aktien Detergent mixtures with improved washing power
US6306916B1 (en) 1995-03-29 2001-10-23 Henkel Kommanditgesellschaft Auf Aktien Pearly luster concentrate with newtonian viscosity
EP0828807A4 (en) * 1995-05-27 1999-01-13 Procter & Gamble Cleansing composition containing polyhydroxy fatty acid amide surfactants
EP0828807A1 (en) * 1995-05-27 1998-03-18 The Procter & Gamble Company Cleansing composition containing polyhydroxy fatty acid amide surfactants
WO1997005224A1 (en) * 1995-07-25 1997-02-13 Henkel Kommanditgesellschaft Auf Aktien Pourable nacreous lustre concentrate
US6147124A (en) * 1995-07-25 2000-11-14 Henkel Kommanditgesellschaft Auf Aktien Pourable nacreous lustre concentrate
JPH11510197A (en) * 1995-07-25 1999-09-07 ヘンケル・コマンディットゲゼルシャフト・アウフ・アクチエン Flowable pearlescent concentrate
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WO1998036048A1 (en) * 1997-02-15 1998-08-20 Henkel Kommanditgesellschaft Auf Aktien Method for producing surfactant pearly luster concentrates
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WO2001025378A2 (en) * 1999-10-07 2001-04-12 Rhodia Consumer Specialties Limited Trading As Albright & Wilson Surfactants Europe Structered surfactant systems containing pearlisers
WO2001025378A3 (en) * 1999-10-07 2002-05-02 Rhodia Cons Spec Ltd Structered surfactant systems containing pearlisers
EP1132079B2 (en) 2000-01-21 2010-05-05 L'oreal Washing composition for keratinic materials comprising a low-ethoxylated sorbitan ester
WO2003066796A1 (en) * 2002-02-09 2003-08-14 Huntsman International Llc Opacifiers
FR2929856A1 (en) * 2008-04-15 2009-10-16 Rhodia Operations Sas PROCESS FOR THE PREPARATION OF CRYSTALS BASED ON A FATTY ACID ESTER
WO2009127596A1 (en) * 2008-04-15 2009-10-22 Rhodia Operations Method for preparing fatty acid ester crystals
US20110071308A1 (en) * 2008-04-15 2011-03-24 Rhodia Operations Process for preparing crystals based on a fatty acid ester
JP2011517693A (en) * 2008-04-15 2011-06-16 ロデイア・オペラシヨン Method for preparing fatty acid ester crystals
US8536356B2 (en) 2008-04-15 2013-09-17 Rhodia Operations Process for preparing crystals based on a fatty acid ester
EP3284807A1 (en) * 2009-08-27 2018-02-21 Clariant International Ltd Pearlescent concentrate and method for producing the same

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