Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/60—Sugars; Derivatives thereof
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
  • A61Q19/10—Washing or bathing preparations
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
  • A61K8/442—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
  • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/60—Sugars; Derivatives thereof
  • A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/02—Preparations for cleaning the hair
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
  • A61K2800/59—Mixtures
  • A61K2800/596—Mixtures of surface active compounds

Definitions

• This invention relates to lathering cleansing formulations containing particular surfactant systems that provide good lathering and low irritation.
• Surfactants are essential components in cleansing formulations such as in shampoos, bath and shower gels, providing cleaning and de-fatting properties as well as lathering capacity. Although the latter is of less importance to the actual performance of a cleansing composition, nevertheless the consumer perceives it as an essential quality of a cleansing composition.
• Current cleansing formulations contain mixtures of various types of surfactants that provide the above-mentioned qualities.
• Anionic surfactants are added because of their good lathering properties. Apart from providing good basic quantities of lather, they also have been found to add to the quality of the lather, in particular to its constitution and to the lather kinetics. Anionic surfactants give lather that is stable, i.e. that does not collapse and remains present for a sufficiently long period of time, even in the presence of fats and hard water. A problem associated with the use of anionic surfactants is their tendency to dry out the skin upon frequent use and to generate intolerance towards this type of surfactants. This in particular is the case in sensitive skin types and in applications for babies. Another problem associated with anionic surfactants is their tendency to cause irritation and stinging, in particular to the eyes and the sensitive skin area around the eyes.
• WO 97/26860 discloses conditioning shampoo compositions which are capable of cleansing and conditioning the hair, comprising a mixture of anionic, nonionic and amphoteric surfactants and a conditioning system comprising at least two particular conditioning polymers.
• WO 98/24409 discloses aqueous compositions of body-cleansing agents with strong foaming action that contain anionic surfactants, alkyl(oligo)glucosides, and a combination of zwitterionic surfactants and ampholytic surfactants.
• anionic surfactants alkyl(oligo)glucosides
• ampholytic surfactants a combination of zwitterionic surfactants and ampholytic surfactants.
• lathering cleansing formulations for personal use, and in particular to provide shampoos, that have good dermal tolerability, more specifically for sensitive skin types and babies.
• lathering cleansing compositions and in particular shampoos that are non-irritating to the skin and in particular to the eyes and the area around the eyes.
• Such formulations that have adequate cleansing capacity, are stable and provide sufficient amounts of lather of good quality and stability.
• the present invention relates to lathering skin-care formulations comprising a surfactant system containing: (a) one or more alkyl or alkenyl oligoglucosides,
• TEP Trans-Epithelial Permeability
• lathering skin-care formulations comprising a surfactant system containing: (a) one or more alkyl or alkenyl oligoglucosides,
• formulations wherein the total concentration of betaine surfactants does not exceed 1.5% are preferred are formulations wherein the total concentration of betaine surfactants does not exceed 1 weight-%.
• formulations having substantially no betaine content are preferred.
• this invention relates to lathering skin-care formulations as mentioned in this specification that contain at least about 2 weight-% of one or more alkyl or alkenyl oligoglucosides.
• those formulations containing at least about 3 weight-% of one or more alkyl or alkenyl oligoglucosides are any of the formulations as specified above or hereinafter having a TEP value which is equal or above about 1.95, or alternatively, which is equal to or above 2.00.
• formulations according to this invention wherein the total concentration of anionic surfactants is lower than 7 weight-%, in particular lower than 5 weight-%, more in particular lower than 4 weight-%, or lower than 3 weight-%, relative to the total weight of the formulation.
• a particular feature of this invention comprises the fact that the anionic surfactants are present in a lesser amount than the sum of all non-anionic surfactants. Therefore the anionic surfactants are referred to as 'co-surfactants'.
• the present invention concerns the use of a mixture comprising components (a), (b) and (c) as specified herein as a surfactant system in a lathering cleansing formulation for personal use.
• any percentage is a weight percentage, expressing the weight-by-weight ratio of the ingredient relative to the total weight of the formulation.
• a, b and c in e.g. [(a + b) : c] and other equations refers to the total weight amount of the components (a), (b) and (c) respectively in the various definitions of the surfactant combinations in the formulations of the present invention.
• the formulations of the invention contain alkyl or alkenyl oligoglucosides, which are known nonionic surfactants, which correspond to formula (I):
• R 1 is an alkyl and/or alkenyl group containing 4 to 22 carbon atoms
• G is a sugar unit containing 5 or 6 carbon atoms
• p is a number of 1 to 10.
• the alkyl and or alkenyl oligoglucosides may be derived from aldoses or ketoses containing 5 or 6 carbon atoms, preferably glucose. Accordingly, the preferred alkyl and/or alkenyl oligoglucosides are alkyl and/or alkenyl oligoglucosides.
• the index p in general formula (I) indicates the degree of ohgomerization (DP), i.e. the distribution of mono- and oligoglucosides, and is a number of 1 to 10.
• the value p for a certain alkyl oligoglucoside is an analytically determined calculated quantity, which is generally a broken number.
• Alkyl and/or alkenyl oligoglucosides having an average degree of ohgomerization p of 1.1 to 3.0 are preferably used.
• Alkyl and or alkenyl oligoglucosides having a degree of ohgomerization of less than 1.7 and, more particularly, between 1.2 and 1.5 are preferred from the applicational perspective.
• the alkyl or alkenyl group R 1 may be derived from primary alcohols containing 4 to 11 and preferably 8 to 10 carbon atoms.
• Typical examples are butanol, caproic alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and the technical mixtures thereof obtained, for example, in the hydrogenation of technical fatty acid methyl esters or in the hydrogenation of aldehydes from Roelen's oxosynthesis.
• alkyl or alkenyl group R 1 may also be derived from primary alcohols containing 10 to 22, in particular 12 to 22 and preferably 12 to 16 carbon atoms. Typical examples are decyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, palmitoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol and technical mixtures thereof which may be obtained as described above. Of particular interest are the so-called cocoglucosides, which have a C 8 . 18 alkyl group mixture derived from coconut fatty alcohols. Alkyl oligoglucosides based on hydrogenated C 1 . 14 coconut oil fatty alcohol having a DP of 1 to 3 are preferred.
• compositions of the invention additionally may contain amphoteric or zwitterionic surfactants.
• amphoteric or zwitterionic surfactants are alkyl betaines, alkyl amidobetaines, aminopropionates, aminoglycinates, imidazolinium betaines, sulfobetaines and amphoacetates. These types of surfactants are all known compounds.
• the formulations in accordance with the present preferably contain only small amounts of betaines, in particular the betaines will be present at the concentrations specified herein.
• formulations that do not substantially contain betaines are formulations that do not substantially contain betaines.
• the latter means that the formulations contain no or only some small amounts of betaines, e.g. less than about 0.5 weight-%, or even less than about 0.3 weight-%, or less than about 0.1 weight-%.
• Betaines are known surfactants, which are mainly produced by carboxyalkylation, preferably carboxymethylation, of amine compounds.
• the starting materials are preferably condensed with halocarboxylic acids or salts thereof, more particularly with sodium chloroacetate, one mole of salt being formed per mole of betaine.
• halocarboxylic acids or salts thereof more particularly with sodium chloroacetate, one mole of salt being formed per mole of betaine.
• unsaturated carboxylic acids for example acrylic acid
• betaines are the carboxyalkylation products of secondary and, in particular, tertiary amines corresponding to formula (II):
• R 2 stands for alkyl and/or alkenyl groups containing 6 to 22 carbon atoms
• R 3 stands for hydrogen or alkyl groups containing 1 to 4 carbon atoms
• R 4 stands for alkyl groups containing 1 to 4 carbon atoms
• n is a number of 1 to 6
• X is an alkali metal and/or alkaline earth metal or an ammonium group, the latter including unsubstituted and substituted ammonium such as alkyl ammonium, alkanol ammonium and glucammonium.
• Typical examples are the carboxymethylation products of hexyl methyl amine, hexyl dimethyl amine, octyl dimethyl amine, decyl dimethyl amine, dodecyl methyl amine, dodecyl dimethyl amine, dodecyl ethyl methyl amine, C 12 . 14 cocoalkyl dimethyl amine, myristyl dimethyl amine, cetyl dimethyl amine, stearyl dimethyl amine, stearyl ethyl methyl amine, oleyl dimethyl amine, C 16 . 18 tallow alkyl dimethyl amine and technical mixtures thereof.
• betaines are carboxyalkylation products of amidoamines corresponding to formula (El):
• Typical examples are reaction products of fatty acids containing 6 to 22 carbon atoms, namely caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselic acid, linoleic acid, linolenic acid, elaeostearic acid, arachic acid, gadoleic acid, behenic acid and erucic acid and technical mixtures thereof, with N, N- dimethyl aminoethyl amine, N,N-dimethyl aminopropyl amine, N,N-diethyl aminoethyl amine and N,N-diethyl aminopropyl amine which are condensed with sodium chloroacetate. It is preferred to use a condensation product of C 8-18 cocofatty acid-N,N- dimethyl aminopropyl amide with sodium chloroacetate.
• betaines which can be added to the formulations according to the invention are the imidazolines that can be represented by formula (IV):
• R 6 represents an alkyl group having 5 to 21 carbon atoms
• R 7 represents a hydroxy group
• polyvalent amines such as, for example aminoethylethanolamine (AEEA) or diethylenetriamine.
• AEEA aminoethylethanolamine
• the corresponding carboxyalkylation products result in mixtures of different multiple-chain betaines.
• Typical examples are the condensation products of the previously mentioned fatty acids with AEEA, preferably imidazoline out off lauric acid or C 12 .
• Alkyl or alkenyl-amphoalkanoates or ampho-dialkanoates can more generally be represented by formula (V) :
• R a represents an alkyl or alkenyl radical containing 10 to 24 carbon atoms, usually the coco or lauryl chains; each Alk represents alkylene, in particular C ⁇ - 4 alkylene, more in particular CH or
• R b represents hydrogen (e.g. in the amphoacetates or amphopropionates) or -Alk- C(O)OM (e.g. in the amphodiacetates or amphodipropionates); and each M represents a hydrogen atom, an alkali metal or an alkaline-earth metal, or an amine or an ammonium group, the latter including unsubstituted and substituted ammonium such as alkyl ammonium, alkanol ammonium and glucammonium.
• alkyl or alkenyl amphoacetates Of interest are the alkyl or alkenyl amphoacetates, alkyl or alkenyl amphodiacetates, the alkyl or alkenyl amphopropionates or the alkyl or alkenyl amphodipropionates.
• alkyl amphoacetates or di-acetates as well as the alkyl ampho-propionates or dipropionates, wherein the alkyl preferably is lauryl or coco.
• alkyl and alkenyl refers to hydrocarbon radicals having from about 4 to about 30 carbon atoms, in particular from about 8 to about 22 carbon atoms.
• Alkyl or alkenyl may also be defined above in relation to the alkyl or alkenylglucosides.
• alkyl or alkenyl aminoalkanoates and the alkyl or alkenyl- iminodialkanoates which can be structurally represented by the following formulae: Rc-NH-Alk-COO-M R c -N(Alk-C00-M) 2
• R c represents an alkyl or alkenyl radical, this can be a radical containing 10 to 24 carbon atoms, usually the coco or lauryl chains; M and Alk are as defined above. Of particular interest are the alkyl or alkenyl aminopropionates.
• Preferred amphoteric surfactants are the amphoacetates and particularly preferred is lauroamphocetate.
• anionic surfactants which are used as co-surfactant in the formulations of the invention are soaps, alkyl benzene- sulfonates, alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, glycerol ether sulfonates, ⁇ -methyl ester sulfonates, sulfofatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, fatty acid ether sulfates, hydroxy mixed ether sulfates, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, mono- and dialkyl sulfosuccinates, mono- and dialkyl sulfosuccinamates, sulfotriglycerides, amide soaps, ether carboxylic acids and salts
• ether sulfates are also known anionic surfactants that are industrially produced by the sulfation of fatty alcohol or oxoalcohol polyglycol ethers with sulfonic or chlorosulfonic acids (CS A) and subsequent neutralization.
• Ether sulfates suitable for the purposes of the invention correspond to formula (VI): R80-(CH 2 CH 2 0)mS0 3 X (VI)
• R is a linear or branched alkyl and/or alkenyl group containing 6 to 22 carbon atoms
• n is a number of 1 to 10
• X is an alkali metal and/or alkaline earth metal, ammonium, alkylammonium, alkanolammonium or glucammonium.
• Typical examples are the sulfates of addition products of on average 1 to 10 and, more particularly, 2 to 5 moles of ethylene oxide onto caproic alcohol, caprylic alcohol, 2- ethyl hexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmitoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol and brassidyl alcohol and technical mixtures thereof in the form of their sodium and/or magnesium salts.
• the ether sulfates may have both a conventional homologue distribution and a narrow homologue distribution. It is particularly preferred to use ether sulfates based on adducts of, on average, 2 to 3 moles of ethylene oxide with technical C 12 - 14 or C 12 - 18 coconut fatty alcohol fractions in the form of their sodium and/or magnesium salts.
• the formulations according to the invention have a total concentration of surfactants (a) + (b) + (c) which is in the range of 0.1 to 20, in particular in the range of 1 to 15 and more in particular in the range of 5 to 13 weight-%, or in the range of 5 to 12 weight-% - relative to the total weight of the formulation.
• compositions according to this invention have the following composition : (a) 0.1 to 20 weight-% alkyl oligoglucosides,
• formulations with following composition : a) 2 to 10 weight-% alkyl oligoglucosides; b) 2 to 10 weight-% amphoteric surfactants; and c) 2 to 5 weight-% anionic co-surfactants; the weight ratio of the alkyl glucosides and amphoteric surfactants to the anionic co- surfactants [(a + b) : c] being such that it is in the range of 2 : 1 to 3 : 1, and that the quantities are completed to 100% by addition of suitable further components.
• formulations as defined in the previous paragraph containing a) 2 to 8 weight-% or in particular 3 to 5 weight-% alkyl oligoglucosides, b) 2 to 5 weight-% amphoteric surfactants and c) 2 to 5 weight-% anionic co-surfactants.
• the surfactants' weight ratio of the alkyl glucosides to amphoteric surfactants to the anionic co-surfactants [a : b : c] is in the range of (1.0 to 1.5) : (1.0 to 1.3) : 1.
• amphoteric surfactants are selected from the group consisting of amphoalkanoates, amphodialkanoates, aminoalkanoates, and imino alkanoates.
• amphoteric surfactants are selected from the group consisting of alkyl or alkenyl amphoacetates, alkyl or alkenyl amphodiacetates, alkyl or alkenyl amphopropionates or alkyl or alkenyl amphodipropionates.
• alkyl amphoacetates or di-acetates as well as the alkyl ampho-propionates or dipropionates, wherein the alkyl moiety preferably is lauryl or coco.
• alkyl and alkenyl by preference refer to hydrocarbon radicals having from about 4 to about 30 carbon atoms, in particular from about 8 to about 22 carbon atoms.
• the lathering formulations according to the present invention may be formulated into a variety of cleansing products such as, for example, shampoos, foam bath formulations, bath and shower gels, and any other cleansing formulations.
• formulations may also contain further auxiliary agents and additives such as mild surfactants, oil components, emulsifiers, superfatting agents, pearlizing waxes, consistency promoters, thickeners, polymers, silicone compounds, fats, waxes, lechitines, phospholipids, stabilizers, biogenic agents, deodorizers, anti-dandruff agents, film formers, swelling agents, XJV protection factors, antioxidants, hydrotropes, preservatives, insect repellents, tyrosin inhibitors, solubilizers, perfume oils, dyes and the like.
• auxiliary agents and additives such as mild surfactants, oil components, emulsifiers, superfatting agents, pearlizing waxes, consistency promoters, thickeners, polymers, silicone compounds, fats, waxes, lechitines, phospholipids, stabilizers, biogenic agents, deodorizers, anti-dandruff agents, film formers, swelling agents, XJV protection factors, antioxidants,
• Optional ingredients of the formulations according to the invention are consistency promoters and thickeners.
• Suitable consistency promoters in particular are fatty alcohols containing 12 to 22 and preferably 16 to 18 carbon atoms and, in addition, partial glycerides. These substances are preferably used in combination with alkyl oligoglucosides and/or fatty acid-N- methyl glucamides of the same chain length and/or polyglycerol poly- 12- hydroxystearates.
• Suitable thickeners are, for example, hydrophilic silica products (Aerosil®), polysaccharides, more especially xanthan gum, guar-guar, agar- agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, also relatively high molecular weight polyethylene glycol monoesters and diesters of fatty acids, polyacrylates (for example Carbopol® and Pemulen-types [Goodrich], Synthalens® [Sigma], Keltrol® [Kelco], Sepigel® [Seppic], Salcare® [Allied Colloids]), polyacrylamides, polymers, polyvinyl alcohol and polyvinyl pyrrolidone.
• Alignil® hydrophilic silica products
• polysaccharides more especially xanthan gum, guar-guar, agar- agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose,
• bentonite for example Bentone® Gel VS-5PC [Rheox], which is a mixture of cyclopentasiloxanc, disteardimonium hectorite und propylene carbonate.
• surfactants such as ethoxylated fatty acid glycerides, esters of fatty acids with polyols, for example pentaerythritol or trimethylol propane, narrow-range fatty alcohol ethoxylates or alkyl oligoglucosides and electrolytes, such as alkali metal or alkaline earth metal salts, in particular the halides, e.g. sodium chloride and ammonium chloride.
• the quantity of consistency promoters and thickeners to be used in the formulations according to the present invention is determined by the desired viscosity of these formulations, which may be in the range of 1000 to 10,000 mPas and preferably in the range 3,000 to 6,000 mPas (Brookfield viscosimeter, spindle 4, 10 r.p.m., at +/-3° C).
• Suitable oil components that can be added are, for example, Guerbet alcohols based on fatty alcohols containing 6 to 18 and preferably 8 to 10 carbon atoms, esters of linear C 6 - 22 fatty acids with linear C 6 . 2 fatty alcohols, esters of branched C 6-13 carboxylic acids with linear C 6-22 fatty alcohols such as, for example, myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl erucate, stearyl myristate, stearyl palmitate, stearyl stearate, stearyl isostearate, stearyl o
• esters of linear C 6 - 2 fatty acids with branched alcohols are particularly 2-ethyl hexanol, esters of hydroxycarboxylic acids with linear or branched C 6 . 2 fatty alcohols, more especially Dioctyl Malate, esters of linear and/or branched fatty acids with polyhydric alcohols (for example propylene glycol, dimer diol or trimer triol) and/or Guerbet alcohols, triglycerides based on C 6 .
• polyhydric alcohols for example propylene glycol, dimer diol or trimer triol
• Guerbet alcohols triglycerides based on C 6 .
• the addition products of ethylene oxide and/or propylene oxide with fatty alcohols, fatty acids, alkylphenols or with castor oil are known commercially available products. They are homolog mixtures of which the average degree of alkoxylation corresponds to the ratio between the quantities of ethylene oxide and/or propylene oxide and substrate with which the addition reaction is carried out. C 12 - 18 fatty acid monoesters and diesters of addition products of ethylene oxide with glycerol are known as refatting agents for cosmetic formulations.
• Suitable partial glycerides are hydroxystearic acid monoglyceride, hydroxystearic acid diglyceride, isostearic acid monoglyceride, isostearic acid diglyceride, oleic acid monoglyceride, oleic acid diglyceride, ricinoleic acid monoglyceride, ricinoleic acid diglyceride, linoleic acid monoglyceride, linoleic acid diglyceride, linolenic acid monoglyceride, linolenic acid diglyceride, erucic acid monoglyceride, erucic acid diglyceride, tartaric acid monoglyceride, tartaric acid diglyceride, citric acid monoglyceride, citric acid diglyceride, malic acid monoglyceride, malic acid diglyceride and technical mixtures thereof which may still contain small quantities of triglyceri.de from the production process. Addition products
• Typical examples of fats are glycerides, i.e. solid or liquid (in this case often also referred to as oils) vegetable or animal products which consist essentially of mixed glycerol esters of higher fatty acids, and suitable waxes are inter alia natural waxes, such as, for example, candelilla wax, carnauba wax, japan wax, esparto grass wax, cork wax, guaruma wax, rice germ oil wax, sugarcane wax, ouricury wax, montan wax, beeswax, shellac wax, spermaceti, lanolin (wool wax), uropygial grease, ceresin, ozokerite (earth wax), petrolatum, paraffin waxes, microcrystalline waxes; chemically modified waxes (hard waxes), such as, for example, montan ester waxes, sasol waxes, hydrogenated jojoba waxes, and synthetic waxes, such as, for example, polyal
• lecithins means those glycerophospholipids formed from fatty acids, glycerol, phosphoric acid and choline by esterification.
• lecithins are therefore also often referred to as phosphatidylcholines (PC).
• PC phosphatidylcholines
• cephalins which are also referred to as phosphatidic acids and are derivatives of l,2-diacyl-sn-glycerol-3-phosphoric acids.
• phospholipids usually means mono- and, preferably, diesters of phosphoric acid with glycerol (glycerol phosphates), which are generally considered to be fats.
• glycerol phosphates glycerol phosphates
• sphingosines and sphingolipids are also suitable.
• Suitable pearlizing waxes that can be added are, for example, alkylene glycol esters, especially ethylene glycol distearate; fatty acid alkanolamides, especially cocofatty acid diethanolamide; partial glycerides, especially stearic acid monoglyceride; esters of polybasic, optionally hydroxysubstituted carboxylic acids with fatty alcohols containing 6 to 22 carbon atoms, especially long-chain esters of tartaric acid; fatty compounds, such as for example fatty alcohols, fatty ketones, fatty aldehydes, fatty ethers and fatty carbonates which contain in all at least 24 carbon atoms, especially laurone and distearylether; fatty acids, such as stearic acid, hydroxystearic acid or behenic acid, ring opening products of olefin epoxides containing 12 to 22 carbon atoms with fatty alcohols containing 12 to 22 carbon atoms and/or polyols containing 2 to 15 carbon
• the superfatting agents that can be added to the formulations may be such substances as, for example, lanolin and lecithin and polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides, the latter also serving as foam stabilizers.
• Suitable cationic polymers that can be added are, for example, cationic cellulose derivatives such as, for example, the quatemized hydroxyethyl cellulose obtainable from Amerchol under the name of Polymer JR 400®, cationic starch, copolymers of diallyl ammonium salts and acrylamides, quatemized vinyl pyrrolidone/vinyl imidazole polymers such as, for example, Luviquat® (BASF), condensation products of polyglycols and amines, quatemized collagen polypeptides such as, for example, Lauryldimonium Hydroxypropyl Hydrolyzed Collagen (Lamequat® L, Gr ⁇ nau), quatemized wheat polypeptides, polyethyleneimine, cationic silicone polymers such as, for example, amodimethicone, copolymers of adipic acid and dimethylaminohy- droxypropyl diethylenetriamine (Cartaretine®, Sandoz),
• Suitable anionic, zwitterionic, amphoteric and nonionic polymers that can be added are, for example, vinyl acetate/crotonic acid copolymers, vinyl pyrrolidone/vinyl acrylate copolymers, vinyl acetate/butyl maleate/isobomyl acrylate copolymers, methyl vinylether/maleic anhydride copolymers and esters thereof, uncrosslinked and polyol- crosslinked polyacrylic acids, acrylamidopropyl trimethylammonium chloride/acrylate copolymers, octylacrylamide/methyl methacrylate/tert.-butylaminoethyl methacrylate/2- hydroxypropyl methacrylate copolymers, polyvinyl pyrrolidone, vinyl pyrrolidone/vinyl acetate copolymers, vinyl pyrrolidone/dimethylaminoethyl methacrylate/vinyl caprolactam
• Suitable silicone compounds are, for example, dimethyl polysiloxanes, methylphenyl polysiloxanes, cyclic silicones and amino-, fatty acid-, alcohol-, polyether-, epoxy-, fluorine-, glucoside- and/or alkyl-modified silicone compounds which may be both liquid and resin-like at room temperature.
• Other suitable silicone compounds are simethicones, which are mixtures of dimethicones with an average chain length of 200 to 300 dimethylsiloxane units and hydrogenated silicates.
• the formulations of the invention may further contain amounts of suitable UV protection factors, biogenic agents such as, for example, tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, deoxyribonucleic acid, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils, plant extracts and vitamin complexes, deodorants, germ inhibitors, enzyme inhibitors, odor absorbers, which are substances which are capable of absorbing and largely retaining odor-forming compounds, film formers, swelling agents such as Pemulen and alkyl-modified Carbopol types (Goodrich).
• biogenic agents such as, for example, tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, deoxyribonucleic acid, retinol, bisabolol, allantoin, phytantriol, panthenol, A
• Suitable solubilizers or hydrotropes are, for example, ethanol, isopropyl alcohol or polyols.
• Suitable preservatives are any of the preservatives mentioned in the European Cosmetic Directive, Annex VI, and comprise, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid and the like.
• Suitable perfume oils are mixtures of natural and synthetic perfumes.
• Natural perfumes include the extracts of blossoms (lily, lavender, rose, jasmine, neroli, ylang- ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, caraway, juniper), fruit peel (bergamot, lemon, orange), roots (nutmeg, angelica, celery, cardamon, costus, iris, calmus), woods (pinewood, sandalwood, guaiac wood, cedarwood, rosewood), herbs and grasses (tarragon, lemon grass, sage, thyme), needles and branches (spruce, fir, pine, dwarf pine), resins and balsams (galbanum, elemi, benzoin, myrrh, olibanum, opoponax).
• Typical synthetic perfume compounds are products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type.
• perfume compounds of the ester type are benzyl acetate, phenoxyethyl isobutyrate, p-tert.butyl cyclohexylacetate, linalyl acetate, dimethyl benzyl carbinyl acetate, phenyl ethyl acetate, linalyl benzoate, benzyl formate, ethylmethyl phenyl glycinate, allyl cyclohexyl propionate, styrallyl propionate and benzyl salicylate.
• Ethers include, for example, benzyl ethyl ether while aldehydes include, for example, the linear alkanals containing 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamen aldehyde, hydroxycitronellal, lilial and bourgeonal.
• suitable ketones are the ionones, ⁇ -isomethylionone and methyl cedryl ketone.
• Suitable alcohols are anethol, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol.
• the hydrocarbons mainly include the terpenes and balsams. However, it is preferred to use mixtures of different perfume compounds which, together, produce an agreeable fragrance.
• Other suitable perfume oils are essential oils of relatively low volatility which are mostly used as aroma components.
• Suitable dyes are any of the substances suitable and approved for cosmetic purposes as listed.
• the formulations of the present invention have a reduced content of anionic surfactants but nevertheless provide good lathering properties. Additionally, the total content of surfactants in the formulations of the invention is lower without negatively impacting their cleaning and lathering performance. This further aids to decreasing irritation and moreover is attractive from and economic point of view.
• the formulations of the invention are well tolerated and are particularly useful for applications on babies and sensitive skin types.
• the formulations specifically can be formulated into shampoos with reduced or low eye stinging.
• the formulations according to the invention have excellent lathering and cleansing properties and because of their mildness they are well suited for application on the skin.
• Tetrasodium EDTA (86%) 0.065 % Glycerine (100%o) 0.500 %
• the surfactants are mixed, whereupon the conditioner (Polyquatemium-10) is added. Then the other ingredients are added in the sequence that they are listed.
• the conditioner Polyquatemium-10
• the Trans-Epithelial Permeability (TEP) assay is used as an in vitro model for ocular irritation based on damage to the permeability barrier of the comeal epithelium.
• the permeability barrier is formed by tight junctions and desmosomes of the outermost cell layers.
• One of the first events to occur when an irritant comes into contact with the comeal epithelium is the loss of the permeability barrier as tight junctions separate.
• the epithelium becomes leaky exposing the underlying stroma to the irritant and eventually cells detach.
• the imbibition of fluid may cause the stroma to swell and the collagen lamellae to separate, resulting in cloudiness.
• Tight junctions are found in several well established epithelial cell lines including MDCK cells.
• a confluent monolayer of MDCK cells grown on a microporous insert exhibits high electrical resistance and does not allow the passage of sodium fluorescein across the membrane.
• the confluent layer of MDCK cells behaves as a functional intact epithelium. After treatment with shampoo, electrical resistance is lost and sodium fluorescein leaks across the membrane to the lower well in a dose related manner.
• MDCK cells seeded into TranswellTM inserts at a density of 1 X 10 5 cells/well
• Insert washed with HBSS before placing in a fresh 24 well plate containing lOOO ⁇ l in each well. 7. 200 ⁇ l of 0.02% sodium fluorescein added to each insert.
• Log EC 50 compared to various components of the modified eye test PCR The number of comeal reactions out of six expressed as a percentage J&J Based on the rating described in the modified eye test.
• MASC maximum comeal score during the 7 day evaluation period for all six rabbits. Average of all in vivo runs.
• MASCJ The maximum conjunctival score during the 7 day evaluation period for all six rabbits. Average of all in vivo runs.
• MADS The maximum daily score during the 7 day evaluation period for all six rabbits. Average of all in vivo runs. Correlation of in vivo and in vitro data was done for 39 formulations:
• Formulations with an EC 50 greater than 2% can be predicted as less than moderate irritants by the TEP.
• Formulations with an EC 50 less than 2% were predicted as moderate irritants or greater by the TEP.
• the TEP assay has a positive predictive value (PV+) of 100% and a negative predictive value (PV-) of 81%.

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• 2004
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