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
  • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
  • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
• • 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
  • A61Q19/00—Preparations for care of the skin
  • A61Q19/10—Washing or bathing preparations
• • 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
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q9/00—Preparations for removing hair or for aiding hair removal
  • A61Q9/02—Shaving preparations
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
  • C11D1/02—Anionic compounds
  • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
  • C11D1/28—Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
  • C11D1/66—Non-ionic compounds
  • C11D1/662—Carbohydrates or derivatives
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
  • C11D1/66—Non-ionic compounds
  • C11D1/83—Mixtures of non-ionic with anionic compounds
• • 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
  • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole

Definitions

• the present invention relates to aqueous surfactant compositions with a content of alpha-sulfo fatty acid disalts and specific alkyl or alkenyl oligoglycosides.
• Anionic surfactants are some of the most widespread interface-active compounds and, apart from being used in detergents and cleaners, are also used for diverse purposes in the field of cosmetics.
• Customary anionic surfactants as are used in particular in cosmetics are the salts of alkyl ether sulfates (alkyl polyether sulfates, fatty alcohol polyglycol ether sulfates, in short also ether sulfates). They are characterized by a strong foaming ability, high cleaning power, low sensitivity to hardness and grease and are used widely for producing cosmetic products such as, for example, hair shampoos, foam or shower baths, but also in hand dishwashing detergents.
• anionic surfactants For many current applications, apart from a good interface-active effect, further requirements are placed on anionic surfactants.
• a high dermatological compatibility is required in particular in cosmetics. Furthermore, an adequate solubility in water, good compatibility with as many as possible of the active ingredients and auxiliaries used in cosmetics, a good foaming ability and good thickenability are generally desired.
• anionic surfactants which can be produced at least partially from biogenic sources and specifically also renewable raw materials.
• surfactants which have no alkoxylated groups and which thus render superfluous in particular the use of ethylene oxide for their production.
• aqueous pastes which comprise an alkyl glucoside and an alpha-sulfo fatty acid disalt.
• the document specifically specifies detergents and cleaners, column 5, lines 16-22 revealing that it concerns the manual cleaning of objects with hard surfaces, such as dishes, and the washing of textiles by hand or in a washing machine.
• the object of the present invention was to provide aqueous surfactant compositions with a content of alkyl or alkenyl oligoglycosides which are characterized by an excellent foaming ability, in particular initial foaming behavior.
• the initial foaming behavior plays a very important role for so-called rinse-off products, which are to be understood as meaning products which come into contact with the skin during cleaning or grooming, but are then washed off again (e.g. shower gels, shower formulations, shampoos, liquid soaps, etc.). In this sector, as large a foam volume as possible is desired.
• aqueous surfactant compositions should moreover have hydrolysis stability both in the acidic and in the alkaline pH range and be as free as possible from constituents which comprise ethylene or propylene oxide building blocks or sulfate groups.
• aqueous surfactant compositions should either be able to be readily thickened to an adequately high viscosity or already by themselves have an adequately high viscosity.
• adequately high viscosity is understood as meaning a value of 1000 mPas or higher and in particular a value in the range from 2000 to 8000 mPas (measured using a Brookfield RV laboratory rheometer at 20° C., 12 rpm, spindle set RV 02 to 07 (spindle choice depending on viscosity range)).
• mPas means millipascal seconds.
• the aqueous surfactant compositions should also have a storage stability at room temperature (23° C.) of more than at least 8 weeks without any kind of visible changes (for example clouding, phase separations and the like) occurring and without viscosity changes or changes in the chemical composition arising.
• the invention firstly provides aqueous surfactant compositions comprising
• radical R 1 is a linear or branched alkyl or alkenyl radical with 6 to 16 carbon atoms and the radicals M 1 and M 2 —independently of one another—are selected from the group H, Li, Na, K, Ca/2, Mg/2, ammonium and alkanolamines, one or more alkyl glycosides (B) of the general formula (II),
• R 2 is an alkyl and/or alkenyl radical with 8 to 18 carbon atoms
• G is a sugar radical with 5 or 6 carbon atoms
• p is numbers between 1 and 10, water
• the compounds (B) it is the case that the fraction of the compounds (B) in which the radical R 2 is an alkyl or alkenyl radical with 15 or more carbon atoms—based on the total amount of the compounds (B) in the aqueous surfactant compositions—is 5% by weight or less; if the aqueous surfactant compositions comprise one or more ester sulfonates (E) of the general formula (V),
• the radical R 5 is a linear or branched alkyl or alkenyl radical with 6 to 18 carbon atoms and the radical R 6 is a linear or branched alkyl or alkenyl radical with 1 to 20 carbon atoms, where the radical R 6 can logically be an alkenyl radical or be branched only above 3 carbon atoms, and the radical M 5 is selected from the group Li, Na, K, Ca/2, Mg/2, ammonium and alkanolamines, it is the case that the compounds (A)—based on the totality of the compounds (A) and (E)—must be present to 50% by weight or more—and in particular to 90% by weight or more; the weight ratio of the compounds (A): (B) in the aqueous surfactant compositions is in the range from 0.6: 1 to 1: 0.6.
• the compounds (A), which are referred to within the context of the present invention as alpha-sulfo fatty acid disalts, are obligatory for the aqueous surfactant compositions according to the invention. They have the aforementioned formula (I)
• the radical R 1 is a linear or branched alkyl or alkenyl radical with 6 to 16 carbon atoms and the radicals M 1 and M 2 —independently of one another—are selected from the group H, Li, Na, K, Ca/2, Mg/2, ammonium and alkanolamines.
• the proviso also applies that the fraction of the compounds (A) in which the radical R 1 is an alkyl or alkenyl radical with 14 or more carbon atoms—based on the total amount of the compounds (A) in the aqueous surfactant compositions—is 20% by weight or less.
• the proviso applies that the fraction of the compounds (A) in the aqueous surfactant compositions in which the radical R 1 is an alkenyl radical—based on the total amount of the compounds (A)—is 3% by weight or less.
• the radical R 1 in the formula (I) means a saturated, linear radical with 10 to 16 carbon atoms, where, with regard to the compounds (A), it is the case that the fraction of the compounds (A) in which the radical R 1 is a decyl and/or a dodecyl radical—based on the total amount of the compounds (A)—is 90% by weight or more.
• radicals M 1 and M 2 in the formula (I) are Na.
• the compounds (A) can be prepared by all methods known appropriately to the person skilled in the art.
• a particularly preferred method of preparation here is the sulfation of the corresponding carboxylic acids.
• the corresponding carboxylic acid and in particular the corresponding fatty acids are reacted with gaseous sulfur trioxide, the sulfur trioxide being used preferably in an amount such that the molar ratio of SO 3 to fatty acid is in the range from 1.0:1 to 1.1:1.
• the crude products obtained in this way, which are acidic sulfation products, are then partially or completely neutralized, preference being given to complete neutralization with aqueous NaOH. If desired, it is also possible to undertake purification steps and/or a bleaching (for adjusting the desired pale color of the products).
• the compounds (A) are used in technical-grade form.
• the corresponding carboxylic acids in particular native fatty acid
• the corresponding carboxylic acids are sulfated with gaseous sulfur trioxide, as a result of which, following partial or complete neutralization of the resulting acidic sulfation products, a mixture of the compounds (A), (C) and (D) results.
• the reaction parameters in particular molar ratio of carboxylic acid and sulfur trioxide, and also reaction temperature
• the content of (A) is in the range from 60 to 100% by weight
• the content of (C) is in the range from 0 to 20% by weight
• the content of (D) is in the range from 0 to 20% by weight, with the proviso that the sum of the components (A), (C) and (D) in this mixture is 100% by weight.
• the content of (A) is in the range from 70 to 80% by weight
• the content of (C) is in the range from 10 to 15% by weight
• the content of (D) is in the range from 10 to 15% by weight, with the proviso that the sum of the components (A), (C) and (D) in this mixture is 100% by weight.
• the compounds (B), which are referred to in the context of the present invention as alkyl glycosides, are obligatory for the aqueous surfactant compositions according to the invention. They have the aforementioned formula (II),
• R 2 is an alkyl and/or alkenyl radical with 8 to 18 carbon atoms
• G is a sugar radical with 5 or 6 carbon atoms
• p is numbers between 1 and 10.
• the proviso also applies that the fraction of the compounds (B) in which the radical R 2 is an alkyl or alkenyl radical with 15 or more carbon atoms—based on the total amount of the compounds (B) in the aqueous surfactant compositions—is 5% by weight or less.
• the radical R 2 can mean either an alkyl or an alkenyl radical and also—as the index p shows—that they can be alkyl or alkenyl oligoglycosides.
• APGs of the form claimed here can be obtained by the relevant methods of preparative organic chemistry.
• the APGs can be derived from aldoses or ketoses with 5 or 6 carbon atoms.
• the APGs are derived from glucose.
• the degree of oligomerization of the APGs is between 1 and 10 and preferably between 1 and 6.
• p in an individual APG molecule must always be an integer and here in particular assumes the values in the range from 1 to 6, the value p for an APG which is a mixture of different APG molecules, which differ in their individual p values, is an analytically determined calculated parameter which in most cases is a fraction.
• APGs are used with an average degree of oligomerization p in the range from 1.1 to 3.0. In this connection, preference is given in particular to those APGs whose average degree of oligomerization is less than 2 and is preferably in the range from 1.1 to 1.8 and in particular in the range from 1.2 to 1.7.
• the average degree of oligomerization here is to be understood in the sense of how it is defined in the monograph K. Hill, W. von Rybinski, G. Stoll “Alkyl Polyglycosides. Technology, Properties and Applications” (VCH-Verlagsgesellschft, 1996) in the section “Degree of polymerization” (compare pages 11-12 of the book): there it reads “The average number of glycose units linked to an alcohol group is described as the (average) degree of polymerization (DP).” In explanatory FIG. 2, which describes a typical distribution of dodecyl glycoside oligomers of an AOPG with a degree of DP of 1.3, the average degree of DP is also described by a corresponding mathematical formula.
• the radical R 2 is preferably derived from primary alcohols with 4 to 11 carbon atoms and preferably 8 to 10 carbon atoms.
• suitable radicals R 2 are butyl, hexyl, octyl, decyl, undecyl, dodecyl and myristyl.
• APGs which are derived from glucose and in which the radical R 2 is a saturated alkyl radical with 8 to 12 carbon atoms and which have an average degree of oligomerization in the range from 1.1 to 3 and in particular in the range from 1.2 to 1.8 and particularly preferably in the range from 1.2 to 1.7.
• These APGs can for example be prepared by reacting a sugar, in particular glucose, under acid catalysis with a fatty alcohol mixture, the fatty acid mixture used preferably being a forerunning produced during the distillative separation of technical-grade C 8-18 -coconut fatty alcohol, which comprises predominantly octanol-1 and decanol-1 and also small amounts of dodecanol-1.
• the aqueous surfactant compositions according to the invention comprise, besides the compounds (A), (B) and water, additionally one or more compounds (C) of the general formula (III)
• the radical R 4 is a linear or branched alkyl or alkenyl radical with 7 to 17 carbon atoms and the radicals M 3 is selected from the group H, Li, Na, K, Ca/2, Mg/2, ammonium and alkanolamines.
• the aqueous surfactant compositions according to the invention comprise, besides the compounds (A), (B) and water, additionally one or more inorganic salts of sulfuric acid (D) of the general formula (IV)
• M 4 is selected from the group Li, Na, K, Ca/2, Mg/2, ammonium and alkanolamine.
• the radicals M 1 and M 2 of the compounds (A), the radical M 3 of the compounds (C) and the radical M 4 of the compounds (D) can be alkanolamines.
• particular preference is given to monoethanolamine, diethanolamine, triethanolamine and monoisopropanolamine.
• the aqueous surfactant compositions according to the invention comprise the compounds (A), (B), (C) and (D).
• M 1 and M 2 of the compounds (A), the radical M 3 of the compounds (C) and the radical M 4 of the compounds (D) has the meaning Na (sodium).
• the content of the compounds (A) and (B) in the compositions—based on the total composition— is at least 1% by weight.
• the content of the compounds (A) and (B) in the compositions—based on the total composition— is in the range from 5 to 50% by weight, in particular in the range from 5 to 20% by weight and particularly preferably in the range from 8 to 12% by weight.
• the weight ratio of the compounds (A):(B) in the aqueous surfactant compositions is in the range from 0.6:1 to 1:0.6.
• the weight ratio of the compounds (A):(B) in the aqueous surfactant compositions is in the range from 0.7:1 to 1:0.7, and especially in the range from 0.8:1 to 1:0.8.
• the range from 0.9:1 to 1:0.9 is very particularly preferred.
• the pH of the compositions is in the range from 4.3 to 5.8.
• the viscosity of the aqueous surfactant compositions is preferably 1000 mPas or higher.
• the aqueous surfactant compositions according to the invention can additionally comprise one or more further surfactants which, in structural terms, do not belong to the aforementioned compounds (A), (B), (D) or (E).
• These surfactants may be anionic, cationic, nonionic or amphoteric surfactants.
• a further subject matter of the invention is the use of the aforementioned compositions for cosmetic products.
• cosmetic products particular preference is given here especially to those which are present in the form of hair shampoos, shower gels, soaps, syndets, washing pastes, washing lotions, scrub preparations, foam baths, oil baths, shower baths, shaving foams, shaving lotions, shaving creams and dental care products (for example toothpastes, mouthwashes and the like).
• SFA-I alpha-sulfo fatty acid disalt of technical grade based on native C 12/14 -fatty acid; composition: 74% by weight disodium 2-sulfolaurate, 13% by weight sodium laurate, 11% by weight sodium sulfate, 2% by weight water.
• the term “laurate” here means that the C12/14 ratio of the mixture of the underlying native fatty acids is 70:30. Active substance content—based on disalt—74% by weight
• APG-I Standard commercial C 12-C16 -fatty alcohol glycoside, active substance content: 50-53% by weight, water fraction: 47-50% by weight, pH about 11.5-12.5 (Planatacare 1200 UP, BASF BPCN)
• an aqueous surfactant solution was firstly prepared as follows: 1 g of active substance of each sample to be tested (the samples used were SFA-I or APG-I or mixtures of these substances, see below; in the case of SFA-I, active substance content is understood—as stated above—as meaning the disalt content) was dissolved at 20° C. in 1 liter of water with a degree of hardness of 15° German hardness (corresponds to 2.673 mmol of CaCO 3 ). The pH of the solution was adjusted to 5.5 with HCl. The solution prepared in this way was heated to 30° C.
• Measurement 250 ml of the heated reservoir were transferred to the measuring instrument and foamed at a speed of 1300 revolutions per minute for 10 seconds, the foam volume then present was ascertained (in ml), then foamed for a further 10 seconds, the foam volume then present was ascertained (in ml), etc., i.e. the foam level was determined every 10 seconds during foaming. After a foaming time of 80 seconds, the measurement was ended. The measurement was repeated for each sample 3 times, in each case using a fresh solution from the same batch, and the result of the measurements after 40, 60 and 80 seconds was given as an average from these three measurements (see table).

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• Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

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• 2014
  • 2014-02-04 ES ES14153833.0T patent/ES2667168T3/es active Active
  • 2014-02-04 EP EP14153833.0A patent/EP2902010B1/de active Active
  • 2014-02-04 PL PL14153833T patent/PL2902010T3/pl unknown
• 2015
  • 2015-01-23 BR BR112016018065-8A patent/BR112016018065B1/pt active IP Right Grant
  • 2015-01-23 KR KR1020167024264A patent/KR102348889B1/ko active Active
  • 2015-01-23 WO PCT/EP2015/051333 patent/WO2015117840A1/de not_active Ceased
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• 2018
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