EP2139594A1 - Nouvelles compositions a base de glycosides d'alkyle, procede pour leur preparation et utilisation comme agents tensioactifs - Google Patents
Nouvelles compositions a base de glycosides d'alkyle, procede pour leur preparation et utilisation comme agents tensioactifsInfo
- Publication number
- EP2139594A1 EP2139594A1 EP08787775A EP08787775A EP2139594A1 EP 2139594 A1 EP2139594 A1 EP 2139594A1 EP 08787775 A EP08787775 A EP 08787775A EP 08787775 A EP08787775 A EP 08787775A EP 2139594 A1 EP2139594 A1 EP 2139594A1
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- European Patent Office
- Prior art keywords
- weight
- composition
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- radical
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Classifications
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/017—Mixtures of compounds
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/835—Mixtures of non-ionic with cationic compounds
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- 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
- A61Q19/04—Preparations for care of the skin for chemically tanning the skin
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/46—Esters of carboxylic acids with amino alcohols; Esters of amino carboxylic acids with alcohols
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- 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
Definitions
- the present invention relates to a novel family of compositions based on alkyl glycosides and alcoholic esters of amino acids, peptides or proteins.
- Another aspect of the invention relates to an advantageous mode of preparation of these compositions.
- compositions as surface-active agents, in particular in the fields of detergency, agrochemistry and cosmetics.
- Alkyl glycosides or polyglycosides are well known nonionic surfactant compounds (J.A.C.S. 60, 2076, 1938; US 6156543; US 5688930). They can be used alone or in combination with other surfactants in a wide range of industrial applications. The properties sought by users depend essentially on the application sectors.
- alkyl glycosides are used as surfactants in the formulation of detergents, cosmetics or agrochemical formulations.
- Detergent is an important sector of use of alkyl glycosides. This use is motivated inter alia by the search for a high surfactant power, by the generation of large foam volumes, by the search for solubilization properties of non-water-soluble compounds and by a favorable ecotoxicity and biodegradability.
- Alkyl glycosides are especially used as an emulsifier in the manufacture of emulsions, mini-emulsions or microemulsions with an aqueous or oily continuous phase (US 6087403, US 6596779, WO 2005110588, WO 2005121294).
- Emulsions are known and widely used in industry either as materials to be consumed or to be applied to surfaces as non-water soluble agents.
- emulsions in cosmetics (milks, creams, ointments), in cooking (sauces, creams), in galenics (ointments, creams), in paint (paint without odor), in the road industry (bitumen in emulsion), in agrochemicals (phytosanitary products), detergents, rolling mills, steelmaking and the manufacture of various deposits (printing, adhesives, etc.).
- emulsions are an effective way to obtain the harmonious combination of ingredients of different nature and properties in a homogeneous and easy-to-use presentation.
- Many phytosanitary compounds are insoluble in water and, being previously solubilized in an organic solvent, they can be emulsified in water at the time of application or formulation by a suitable choice of glycoside-type emulsifiers. alkyl.
- the good foaming power of alkyl glycosides is a tare in the cleaning of surfaces by auto-washer, high-pressure lance or in the "washing in place" operations of the food industry, washing bottles or automatic washing of dishes.
- foam volumes interfere with washing and rinsing and decrease the efficiency of operations.
- the formulator will have to add to the detergent based on alkyl polyglycosides a compound with non-foaming properties or "anti-foams" to reduce the phenomenon.
- the anti-foam agents generally used are of petrochemical origin and expensive. They also have an unacceptable environmental profile. There is therefore a need for new compositions based on alkyl glycosides whose foaming capacity can be controlled.
- the alkyl glycosides sometimes exhibit instability at dilution which results in a loss of the effectiveness of the detergents, in particular with regard to the surfactant activity. There is therefore still a need for new compositions based on stable alkyl glycosides whose efficiency makes it possible to lower the surface tension at low concentrations.
- alkyl glycosides do not always make it possible to formulate emulsions that are sufficiently stable over time (WO 92/06778, WO 95/13863, WO / 9822207). These emulsions are also known to not tolerate the presence of electrolytes.
- the formulator to overcome this defect, will combine its emulsifying system with additives such as polymers or complexing agents that are expensive and difficult to implement. There is therefore also a need for compositions based on alkyl glycosides whose emulsifying power is improved, especially in the presence of electrolyte.
- alkyl glycosides can be improved by association with alcoholic esters of amino acids, peptides or proteins.
- the present invention also relates to an advantageous mode of obtaining these compositions.
- the invention relates to the uses of these compositions as surfactants for the preparation of detergents, cosmetics or agrochemical formulations.
- a first aspect of the invention relates to new compositions based on alkyl glycosides whose physicochemical properties and biodegradability are improved by the presence of at least one compound chosen from alcoholic acid amino acid, peptide or protein.
- compositions according to the invention are characterized in that they comprise: i) from 70 to 99% by weight of the composition of at least one compound of formula (1)
- R1 is a linear or branched, saturated or unsaturated hydrocarbon-based radical having from 1 to 4 ethylenic unsaturations, having from 1 to 36 carbon atoms, preferably having from 4 to 22 carbon atoms;
- Gl, G2, G3, G4, G5 are independently of each other, the remains of an ose selected from hexoses, parabinose and xylose
- a, b, c, d and e are equal to 0 or 1, the sum of a, b, c, d and e being at least equal to 1 ii) from 1 to 30% by weight of the composition of at least one compound of formula (2) or a salt thereof,
- R2 is a radical chosen from: -CH3, - (CH2) 3-NH- C (NH) -NH2, -CH2-CO-NH2, -CH2-CO-OR3, -CH2-SH - (CH 2) 2 -CO-NH 2, - (CH 2) 2 -CO-OR 3, H, -CH 2 - (C 3 H 3 N 2), -CH (CH 3) -CH 2 -CH 3, -CH 2 -CH (CH 3) -CH 3, - (CH2) 4-NH2, - (CH2) 2-S-CH3, -CH2-C6H5, -CH2-OH, -CH (OH) -CH3, -CH2- (C8H6N), -CH2- (C6H4) - OH, -CH (CH3) -CH3
- R2 is the following cyclic radical: - (CH2) 2 -Y-, Y represents a methylene group -CH2- linked to X
- R3 being optionally identical to R1, is a linear or branched, saturated or unsaturated hydrocarbon-based radical having from 1 to 4 ethylenic unsaturations, having from 1 to 36 carbon atoms, preferably having from 4 to 22 carbon atoms;
- n is an integer greater than or equal to 1; and when n is greater than 1, then R2 represents several radicals as defined above identical or different from each other.
- R 1 Particularly preferred for R 1 are alkyl radicals and particularly those derived from alcohols or primary or secondary acids having from 1 to 36 carbon atoms, preferably having from 4 to 22 carbon atoms.
- alkyl radicals are the methyl, ethyl, butyl, octyl and decyl radicals, as well as the radicals derived from alcohols or capric, lauric, myristic, palmitic, stearic, oleic and erucic acids and more generally the radicals derived from carboxylic acids.
- the remnants of reducing sugars in particular hexoses and or pentoses, such as glucose, galactose, mannose, sorbose, arabinose or xylose, are preferred.
- the reducing sugars may in particular be derived from the hydrolysis of oligosaccharides or polysaccharides.
- the alkyl glycosides or polyglycosides used in the present invention may be synthesized by the many methods of organic chemistry known to date.
- a route conventionally used for the preparation of alkyl glycosides is an acetalization reaction. This method consists in bringing into contact one or more reducing sugars and one or more excess alcohols (molar ratio of sugars / alcohols between 1 / 1.5 and 1/10) in the presence of a catalytic amount of acid (from 0 , 1 to 5% by weight relative to the weight of the sugars engaged), at a temperature of between 50 and 140 0 C for a period of 15 minutes to 6 hours and to remove water from the reaction medium to obtain a solution of alkyl glycosides and optionally to separate the alkyl glycosides from this solution.
- acid catalyst sulfuric acid, sulfonic acid such as methanesulfonic acid, hydrochloric acid, hypophosphorous acid or any other acid catalyst for effecting the reaction.
- a solvent such as an ether-oxide such as tetrahydrofuran, diethyl ether, 1,4-dioxane, isopropyl ether, methyl- tert-butyl ether, ethyl tert-butyl ether or diglyme, a halogenated hydrocarbon or a solvent of the amide family such as N, N-dimethylformamide, an alkane such as hexane or an aromatic solvent such as toluene.
- a solvent such as an ether-oxide such as tetrahydrofuran, diethyl ether, 1,4-dioxane, isopropyl ether, methyl- tert-butyl ether, ethyl tert-butyl ether or diglyme, a halogenated hydrocarbon or a solvent of the amide family such as N, N-dimethylformamide, an alkane such as hexane or an
- reaction solvent can be removed, if it is present.
- the acid catalyst can then be neutralized and the solution filtered.
- the neutralization will be carried out, for example, with an alkali metal or alkaline earth metal hydrogencarbonate or carbonate, especially sodium hydrogen carbonate, with an alkali or alkaline earth metal hydroxide, in particular sodium hydroxide, or with an organic base such as than triethanolamine.
- glycosides alkyl may then be purified glycosides alkyl or by evaporation of excess alcohol under vacuum of between 0.1 and 100 mbar to a temperature of between 60 and 200 ° C, preferably using a thin film evaporator or by column chromatography on silica gel, alumina, activated charcoal or ion exchange resin, or by crystallization in a solvent.
- the alkyl glycosides can be decolorized by adding, at a temperature of between 15 and 100 ° C., 0.05 to 10% by weight and preferably from 0.5 to 8% by weight of hydrogen peroxide, alkali or alkaline earth metal peroxodisulphates, perborates, persulfates, perphosphates, percarbonates, ozone or even periodates. Hydrogen peroxide will be preferred at 30 or 50%.
- the alkyl glycosides can be prepared from sources of pure or mixed sugars. Accordingly, compositions based on alkyl glucosides, alkyl xylosides, alkyl arabinosides or mixtures of these three types of alkyl glycosides can be prepared.
- the alkyl glycosides used for the preparation of the compositions may in particular correspond to the surfactants or compositions described in US 6156543, US 5688930, US 6596779, US 6087403, WO 2005110588 and WO 2005121294 in the name of the applicant.
- glycosides alkyls obtained from reducing sugar syrups derived from vegetable raw materials rich in starch and hemicellulose or products or co-products of agricultural origin such as bagasse, co-products of corn (bran, fibers and corn stover), sorghum co-products, co-products of barley (bran), co-products of rice or co-products of wheat, oats (bran and straw) containing hexose polymers and pentoses.
- alkyl glycosides derived from wheat bran and wheat straw or corn bran, fibers and fibers and comprising from 1 to 99% by weight of alkyl hexosides in respect of all glycosides and from 1 to 99% by weight of alkyl pentosides.
- the average degree of polymerization (DP m ) of the alkyl glycosides used in the invention is preferably between 1 and 5 and more particularly between 1 and 3.
- the alkyl glycosides used will be in the form of aqueous solutions preferably having a solids content of 30 to 90% by weight. Depending on the nature of the alcohol or mixture of alcohols used for the synthesis, they may also be in the form of a solid, pasty or liquid wax, optionally mixed with the alcohol or the starting fatty alcohols. .
- any compound of formula (2) may be in a salt form of its amine function. It may in particular be an ammonium salt whose counterion is a halide such as, for example, the chloride ion, a bromide, an iodide, a sulphate, an alkylsulphate such as, for example, CH 3 OSO 3 -, an alkyl sulphonate, for example Example CH 3 SO 3 -, CH 3 C 6 H 4 SO 3 -, a phosphate, an alkylphosphate, a nitrate, a hydroxide, an alkoxide or a carboxylate.
- a halide such as, for example, the chloride ion, a bromide, an iodide, a sulphate, an alkylsulphate such as, for example, CH 3 OSO 3 -, an alkyl sulphonate, for example Example CH 3 SO 3 -, CH 3 C 6 H 4 SO 3 -,
- the compound of formula (2) may be in its "free amine” form or in a partially or totally salified form.
- the compounds of formula (2) are known from the state of the art, they can in particular be obtained by esterification of compounds of formula (3) according to the procedures of the state of the art or of their salts, in the presence an alcohol of formula R 3 OH with R 3 as defined above.
- R2 is a radical chosen from: -CH3, - (CH2) 3-NH- C (NH) -NH2, -CH2-CO-NH2, -CH2-CO-OR3, -CH2-SH - (CH2) 2-CO-NH2, - (CH2) 2-CO-OR3, H, -CH2- (C3H3N2), -CH (CH3) -CH2-CH3, -CH2- CH (CH3) -CH3, - (CH2) 4-NH2, - (CH2) 2-S-CH3, -CH2-C6H5, -CH2-OH, -CH (OH) -CH3, -CH2- (C8H6N), -CH2- (C6H4) -OH, -CH (CH3) -CH3
- R2 is the following cyclic radical: - (CH2) 2 -Y-, Y represents a methylene group -CH2- linked to X
- n is an integer greater than or equal to 1; and when n is greater than 1, then R2 represents several radicals as defined above identical or different from each other.
- the compound of formula (3) represents an amino acid selected from glycine, alanine, serine, aspartic acid, glutamic acid, glutamine, valine, threonine, arginine, lysine, proline, leucine, phenylalanine, isoleucine, histidine, tyrosine, tryptophan, asparagine, cysteine, cystine, methionine, hydroxyproline, hydroxylysine, ornithine.
- the compound of formula (3) represents a peptide or a protein.
- amino acids, peptides or proteins may be of animal origin, such as, for example, collagen, elastin, fish flesh protein, fish gelatin, keratin or casein.
- amino acids, peptides and proteins of vegetable origin such as, for example, those derived from soybean, rapeseed, sunflower, oats, wheat, maize, barley, potato, alfalfa, lupine, faba bean, sweet almond, silk, and more generally, those derived from all lignocellulosic plant material constituting the bulk of annual and perennial plants.
- Annual plant means any plant with a vegetative life of the order of a year (such as cereals and various grasses, hemp, flax, sugar cane %) and perennial plant, plants whose development extends over a longer period (such as bamboo, hardwoods, softwoods ).
- Ligno-cellulosic material refers to whole plants or parts of the said plants (stems, bark, %) or by-products of the industrial sector of production for food purposes (wheat straw, barley rice, bagasse of sugar cane bagasse sorghum sugar ).
- the amino acids or peptides may themselves be obtained by total or partial hydrolysis of a protein of any origin. This hydrolysis can be carried out for example by heating at temperatures between 60 and 130 ° C. of a protein placed in an acidic or alkaline medium. It can also be carried out enzymatically using a protease.
- esterification reaction of the amino acids, peptides or proteins will be carried out by the methods known to those skilled in the art.
- the enzymatic methods described in the patents WO 9318180 and WO 9517518 or the chemical methods described in "Interfacial phenomena in biological systems, edition M. Bender, the method described in J. Biol. Chem. 161, 259-269, 1945 or in US Patent 5780658.
- the acid catalyst sulfuric acid, a sulfonic acid such as methanesulfonic acid, hydrochloric acid, hypophosphorous acid or any other acid catalyst for carrying out the reaction.
- a solvent such as an ether ether such as tetrahydrofuran, diethyl ether, 1,4-dioxane, isopropyl ether, methyl- tert-butyl ether, ethyl tert-butyl ether or diglyme, a halogenated hydrocarbon or a solvent of the amide family such as N, N-dimethylformamide, an alkane such as hexane or an aromatic solvent such as toluene.
- a solvent such as an ether ether such as tetrahydrofuran, diethyl ether, 1,4-dioxane, isopropyl ether, methyl- tert-butyl ether, ethyl tert-butyl ether or diglyme, a halogenated hydrocarbon or a solvent of the amide family such as N, N-dimethylformamide, an alkane such as hexane or an aromatic solvent
- the reaction solvent may be removed, if it is present.
- the acid catalyst can then be neutralized and the solution filtered.
- the neutralization for example, with an alkali metal or alkaline earth metal hydrogencarbonate or carbonate, especially sodium hydrogen carbonate, with an alkali metal or alkaline earth metal hydroxide, especially sodium hydroxide, or with an organic base such as than triethanolamine.
- the ester or mixture of esters of formula (2) can then be purified either by evaporation of the excess alcohols in a vacuum of between 0.1 and 100 mbar at a temperature of between 60 and 200 ° C., preferably by means of a layer evaporator thin, either by column chromatography on silica gel, alumina, activated charcoal or ion exchange resin, or by crystallization in a solvent.
- the compounds of formula (2) can be characterized by the establishment of molecular masses by mass spectrometry. Their concentration can also be determined by nitrogen determination according to the known Kjeldahl method, for example.
- the second aspect of the invention is a process for the advantageous preparation of the compositions according to the invention.
- compositions are predominantly composed of alkyl pentosides but comprise only a very small amount of compounds of amino acid esters, peptides or proteins type.
- Patents EP 0699472 (which we will call Dl document), and Patent WO 9729115 (which we will call D2 document) in the name of the applicant, describe processes for the preparation of glycoside surfactants which consist in bringing wheat bran into contact with a wheat. acidic aqueous solution and / or an enzymatic complex. Thus, a pentose juice is obtained which must be removed from the marc (lignocellulosic residue).
- the juice freed from its marc must then be concentrated (distillation of water) before being used in glycosylation of an alcohol having from 6 to 22 carbon atoms, which makes it possible to obtain a mixture of pentosides.
- the pentosides are obtained from the pentoses by a first glycosylation reaction with butanol and then by transglycosylation with a fatty alcohol.
- the compositions obtained as in Examples 1 of D1 and D2 do not contain more than 0.5% of amino acid esters, peptides or proteins, since their nitrogen levels, measured using the method Kjeldhal nitrogen is not greater than 0.01% by weight with respect to the surfactant composition.
- Example 1 of the Dl document only 21 grams of pentosides are obtained from 326 grams of Son. Similarly, in Example 1 of D2, 147 grams of pentosides are obtained from 231 grams of barley bran.
- the process according to the present invention makes it possible to obtain better yields of surfactants and furthermore has a reduced number of unit operations compared to the state of the art, and therefore a significant economic advantage.
- This method consists in putting the plant material in direct contact with an alcohol in the presence of a catalyst to obtain the pentoside solution.
- the material is not brought into contact with water, as is the case in D1 and D2.
- the mechanism is very different from D1 and D2 because it is a direct transglycosylation of pentosans in pentosides in fatty alcohol.
- the process does not pass through "Pentoses juice”. It then becomes unnecessary to purify and concentrate the pentoses since they are directly converted into glycoside surfactants.
- the reaction is carried out without butanol solvent as is the case in Dl and D2.
- the method according to the present invention is therefore easier to implement since it comprises a single unit operation and moreover, makes it possible to obtain better yields.
- the mechanism concerned by the process according to the present invention is schematized below, and accounts for the advantage thereof in comparison with the method described in D1 and D2:
- the present process is characterized in that it consists in putting one or more lignocellulosic plant materials constituting most of the annual and perennial plants and comprising at least starch and / or hemicelluloses and at least one protein or a peptide, in contact with an excess of at least one alcohol having from 1 to 36 carbon atoms (mass ratio of vegetable materials / alcohol of between 1/100 and 1) in the presence of an amount of acid (ratio mass of plant / acid materials between 1 and 100) between 20 and 200 ° C, preferably between 70 and 150 ° C, for at least 5 seconds to obtain a composition according to the invention, if necessary, to neutralize the acid, to rid the composition of a solid marc and / or unreacted alcohol.
- Annual plant means any plant with a vegetative life of the order of one year (such as cereals and various grasses such as maize, sorghum, barley and wheat, hemp, hn, cane sugar %) and perennial plant, plants whose development extends over a longer period (such as bamboo, hardwoods, softwoods ).
- Ligno-cellulosic plant materials are whole plants or parts of the said plants (stems, bark, %) or co-products of industrial production chain for food purpose (wheat straw, rice, barley, bagasse cane sugar, bagasse sorghum sugar ).
- the process according to the invention has the advantage of obtaining in a single unit operation effective surfactant compositions unlike the processes described in the Dl and D2 patents on behalf of the applicant, which require the execution of several operations of hydrolysis and consumption concentration of water and complex glycosylation, especially in the case of the use of higher fatty alcohols.
- alkyl radicals of 1 to 36 carbon atoms, preferably having 1 to 22 carbon atoms
- Typical examples of alkyl radicals are the methyl, ethyl, butyl and octyl radicals, as well as the radicals derived from alcohols or capric, lauric, myristic, palmitic, stearic, oleic and erucic acids and more generally the radicals derived from the original acids.
- sulphonic acids such as benzenesulphonic acid, para-toluenesulphonic acid, camphorsulphonic acid, alkylbenzene sulphonic acid, sulphosuccinic acid or an alkyl sulphosuccinate such as decyl or lauryl sulfosuccinate
- perhalohydric acids such as perchloric acid.
- anionic surfactants such as alkyl ether sulfates, such as lauryl ether sulfate also known under the acronym LES, sodium dodecyl sulphate, also known under the acronym SDS, or the sulfuric or phosphoric esters of alcohols.
- the contacting is carried out for at least 5 seconds and preferably for 5 to 240 minutes in a mixer.
- We can operate at atmospheric pressure, under partial vacuum or in a reactor under pressure of 2 to 100 bar. Is preferred to conduct the reaction in the total absence of solvents, but it may optionally use a solvent such as an ether oxide such as tetrahydrofuran, diethyl ether, 1,4-dioxane, 1 "isopropyl ether, methyl- tert-butyl ether, ethyl-tertiarybutyl ether or diglyme, a halogenated hydrocarbon or a solvent of the amide family such as N 5 N- dimethylformamide, an alkane such as hexane or an aromatic solvent such as toluene.
- a solvent such as an ether oxide such as tetrahydrofuran, diethyl ether, 1,4-dioxane, 1 "isopropyl ether, methyl-
- the acid catalyst can then be neutralized and the solution filtered.
- the filtration residue may also be treated so as to recover the solvents, alcohols or compounds of the compositions.
- the composition will be neutralized before or after possible filtration, for example by an alkali metal or alkaline earth metal hydrogencarbonate or carbonate, especially sodium hydrogencarbonate, with an alkali metal or alkaline earth metal hydroxide. especially soda, or with an organic base such as triethanolamine.
- the excess alcohols can be evaporated under vacuum between 0.1 and 100 mbar at a temperature of between 60 and 200 ° C., preferably by means of a thin-film evaporator.
- the composition may also be purified either by column chromatography on silica gel, alumina, activated charcoal or ion exchange resin, or by crystallization in a solvent.
- compositions according to the invention can be bleached by adding, at a temperature of between 15 and 100 ° C., 0.05 to 20% by weight and preferably from 0.5 to 10% by weight of hydrogen peroxide.
- hydrogen peroxide peroxodisulfates of alkali or alkaline earth metals, perborates, persulfates, perphosphates, percarbonates, ozone or even periodates.
- Hydrogen peroxide will be preferred at 30 or 50% solids.
- compositions according to the invention may be used in the form of an aqueous solution comprising, for example, from 30 to 80% of dry matter.
- compositions according to the invention may be used in a form of non-aqueous solution, that is to say solubilized in a solvent.
- the invention therefore relates to a composition characterized in that it comprises: i) from 30 to 95% by weight of the solvent composition ii) from 4 to 69.3% by weight of the composition of at least one compound of formula
- R1 is a linear or branched, saturated or unsaturated hydrocarbon-based radical having from 1 to 4 ethylenic unsaturations, having from 1 to 36 carbon atoms, preferably having from 4 to 22 carbon atoms;
- G1, G2, G3, G4, G5 are independently of each other, the remains of an ose chosen from hexoses, arabinose and xylose
- A, b, c, d and e being equal to 0 or 1, the sum of a, b, c, d and e being at least equal to 1 iii) of 0.05 to 14% by weight of the composition at least one compound of formula (2) or a salt thereof,
- R2 is a radical chosen from: -CH3, - (CH2) 3-NH- C (NH) -NH2, -CH2-CO-NH2, -CH2-CO-OR3, -CH2-SH - (CH 2) 2 -CO-NH 2, - (CH 2) 2 -CO-OR 3, H, -CH 2 - (C 3 H 3 N 2), -CH (CH 3) -CH 2 -CH 3, -CH 2 -CH (CH 3) -CH 3, - (CH2) 4-NH2, - (CH2) 2-S-CH3, -CH2-C6H5, -CH2-OH, -CH (OH) -CH3, -CH2- (C8H6N), -CH2- (C6H4) - OH, -CH (CH3) -CH3
- R2 is the following cyclic radical: - (CH2) 2 -Y-, Y represents a methylene group -CH2- linked to X
- R3 being optionally identical to R1, is a linear or branched, saturated or unsaturated hydrocarbon-based radical having from 1 to 4 ethylenic unsaturations, having from 1 to 36 carbon atoms, preferably having from 4 to 22 carbon atoms;
- n is an integer greater than or equal to 1; and when n is greater than 1, then R2 represents several radicals as defined above identical or different from each other.
- -Oils of vegetable origin such as coconut oil, castor oil, rapeseed oil, sunflower oil, soybean oil,
- Synthetic oils such as poly- ⁇ -olefins
- Alkanediols having 2 to 10 carbon atoms such as 1,2-propanediol or 1,3-butanediol,
- R 4 OH where R 4 is a saturated or unsaturated aliphatic radical having 1 to 4 ethylenic unsaturations, linear or branched, having 1 to 36 carbon atoms, such as myristic alcohol, cetyl alcohol, alcohol stearic, oleic alcohol,
- R 5 and R 6 are, independently of one another, saturated or unsaturated aliphatic radicals having 1 to 4 linear or branched ethylenic initiations having from 1 to 22 atoms of carbon, such as alkyl myristates including butyl myristate, propyl myristate, alkyl palmitates such as isopropyl palmitate, alkyl stearates including hexadecyl stearate, alkyl oleates , especially dodecyl oleate, alkyl laurates, in particular hexyl laurate, propylene glycol dicaprylate, 2-ethylhexyl cocoate, esters of lactic acid, succinic acid , behenic acid, isostearic acid such as isostearyl isostearate, fatty acid esters of rapeseed, sunflower fatty acids, linseed fatty acids,
- silicone oils comprising cyclic polydimethylsiloxanes, hydroxylated polydimethylsiloxanes, trimethylsilylated polydimethylsiloxanes, polyorganosiloxanes such as polyalkylmethylsiloxanes, polymethylphenylsiloxanes, polydiohismelsiloxanes, amino derivatives of silicones, silicone copolyethers or mixed silicone derivatives such as mixed copolymers polyalkylmethylsiloxane silicones copolyethers.
- compositions of the present invention have properties or surfactant performance enhanced and variable depending on the nature of the constituents.
- enhanced surfactant properties or performance means properties or surfactant performance superior to the surfactant properties or performance of compositions similar in all respects to the compositions of the present invention but not comprising any compound of formula (2). These enhanced properties are obtained through the combination of alkyl glycosides of formula (1) and surfactants of formula (2).
- the compositions of the present invention possess critical micellar concentrations (CMCs) below the CMCs of APGs known in the art. By critical micellar concentration is meant the minimum concentration of surfactants required to obtain micellar aggregates and from which a more or less abrupt variation of the physicochemical properties of the surfactant solution, for example surface tension, is observed. .
- the soil solubilization mechanism intervenes only when the concentration of the surfactants is higher than the critical micelle concentration.
- the first advantage of the compositions of the invention is that products such as detergents with reduced surfactant doses can be prepared.
- compositions according to the invention have improved stability at low concentrations, and therefore, increased performance.
- C20 is a criterion for evaluating the surfactant performance of a composition at low concentrations. It corresponds to the concentration of composition required to lower the surface tension of water by 20 mN / m.
- the compositions according to the invention have improved C20s with respect to the alkyl glycosides of the state of the art.
- CMC Critical Micellar Concentration
- compositions according to the invention characterized in that they comprise: i) from 80 to 99% by weight of the composition of a mixture of compounds of formula
- R 1 is a linear or branched, saturated or unsaturated hydrocarbon radical having from 1 to 4 ethylenic unsaturations, having from 5 to 22 carbon atoms,
- G1, G2, G3, G4, G5 are independently of each other, the remains of an ose chosen from hexoses, arabinose and xylose
- A, b, c, d and e being equal to 0 or 1, the sum of a, b, c, d and e being at least equal to 1 arabinosides and alkyl xylosides representing at least 30% by weight of all the compounds of formula (1). ii) from 1 to 20% by weight of the composition of at least one compound of formula (2) or a salt thereof,
- R2 is a radical chosen from: -CH3, - (CH2) 3-NH- C (NH) -NH2, -CH2-CO-NH2, -CH2-CO-OR3, -CH2-SH - (CH 2) 2 -CO-NH 2, - (CH 2) 2 -CO-OR 3, H, -CH 2 - (C 3 H 3 N 2), -CH (CH 3) -CH 2 -CH 3, -CH 2 -CH (CH 3) -CH 3, - (CH2) 4-NH2, - (CH2) 2-S-CH3, -CH2-C6H5, -CH2-OH, -CH (OH) -CH3, -CH2- (C8H6N), -CH2- (C6H4) - OH, -CH (CH3) -CH3
- R2 is the following cyclic radical: - (CH2) 2 -Y-, Y represents a methylene group -CH2- linked to X
- R3 being optionally identical to R1, is a linear or branched, saturated or unsaturated hydrocarbon radical having from 1 to 4 ethylenic unsaturations, having from 5 to 22 carbon atoms, Where n is an integer greater than or equal to 1; and when n is greater than 1, then R2 represents several radicals as defined above identical or different from each other. and characterized by CMC lower than 800 mg / l and C20 lower than 100 mg / l.
- compositions described above are also characterized by a wetting power superior to APG of the state of the art.
- the wetting power is measured according to the ISO 8022 or NFT 73420 standard describing the measurement of wetting power on cotton support.
- the wetting power corresponds to the wetting time of an unbleached cotton disc placed in a solution of surfactants at a defined concentration.
- 700 ml of a 1 g / l test solution of surfactant composition in distilled water are placed in a beaker thermostated at the desired temperature (20 ° C).
- the experimental measurement can be carried out at the neutral pH of the distilled water or in basic medium (NaOH).
- the wetting time is experimentally determined by means of a stopwatch, t 0 corresponds to the moment when the lower part of the disc touches the solution and t is final when the disc sinks by itself into the solution, t final is also called wetting time.
- Ten consecutive measurements are made with the same solution while taking care however to discard the used cotton discs after each measurement. It is specified here that a surfactant is all the more wetting that the measured wetting time is short.
- the compositions according to the invention have wetting times according to the NFT 73-406 standard of less than 100 seconds and more particularly less than 80 seconds.
- compositions of the invention relate to their foaming property.
- foaming property is meant the property of a composition to form foam under the effect of a mechanical action (stirring, falling of liquid, dispersion of gas).
- Foam can be an advantage when it represents, for example, an indication of the effectiveness of a product (dishwashing liquid, laundry for washing by hand ...) or when it brings a feeling of comfort to the user (soap, shampoo).
- it is a disadvantage when it provokes for example the overflow of a washing machine or the stopping of an industrial machine for washing the floors.
- the compositions of the present invention will be custom-made for the application. We will therefore choose to prepare compositions according to the invention having the property of forming either low quantities, ie large amounts of foam. The foam formed will either be stable or unstable over time and may be more or less resistant to the hardness of the water.
- the foaming properties of the compositions are evaluated by the test of foaming power called the Ross Miles test, according to the French standard NF-T-73-404 of November 1966.
- This test can for example consist of measuring over time and at a temperature of 50 ° C., the volume of foam obtained after the fall, from a height of 450 mm, of 500 ml of a surfactant solution at 0.1% by weight of surfactant composition in demineralized water, on a liquid surface of the same solution (50ml) contained in a thermostated test tube.
- the volume measured just after the liquid drop represents the foaming capacity expressed in foam volume and foaming stability is the foam volume ratio at 20 minutes on foaming capacity expressed as a percentage.
- compositions according to the invention characterized in that they comprise: i) from 80 to 99% by weight of the composition of a mixture of compounds of formula
- R 1 is a linear or branched, saturated or unsaturated hydrocarbon radical having from 1 to 4 ethylenic unsaturations, having from 5 to 22 carbon atoms,
- G1, G2, G3, G4, G5 are independently of each other, the remains of an ose selected from hexoses, arabinose and xylose
- A, b, c, d and e being equal to 0 or 1, the sum of a, b, c, d and e being at least equal to 1, the alkyl hexosides then representing less than 90% by weight of all of the compounds of formula (1). ii) from 1 to 20% by weight of the composition of at least one compound of formula (2) or a salt thereof,
- R2 is a radical chosen from: -CH3, - (CH2) 3-NH- C (NH) -NH2, -CH2-CO-NH2, -CH2-CO-OR3, -CH2-SH - (CH2) 2-CO-NH2, - (CH2) 2-CO-OR3, H, -CH2- (C3H3N2), -CH (CH3) -CH2-CH3, -CH2- CH (CH3) -CH3, - (CH2) 4-NH2, - (CH2) 2-S-CH3, -CH2-C6H5, -CH2-OH, -CH (OH) -CH3, -CH2- (C8H6N), -CH2- (C6H4) -OH, -CH (CH3) -CH3
- R2 is the following cyclic radical: - (CH2) 2 -Y-, Y represents a methylene group -CH2- linked to X
- R3 being optionally identical to R1, is a linear or branched, saturated or unsaturated hydrocarbon radical having from 1 to 4 ethylenic unsaturations, having from 5 to 22 carbon atoms,
- R2 represents several radicals as defined above identical or different from each other. and in that they have a foam volume greater than 200 ml and a stability of the foam at 20 minutes of at least 70% according to the Ross Miles test of the NF-T-73-404 standard carried out at 50 ° C. with a demineralised water solution comprising 0.1% by weight of composition described above.
- compositions according to the invention characterized in that they comprise: i) from 80 to 99% by weight of the composition of a mixture of compounds of formula, will therefore be preferred for their weakly and non-foaming properties;
- R1 is a linear or branched, saturated or unsaturated hydrocarbon radical having from 1 to 4 ethylenic unsaturations, having from 2 to 10 carbon atoms,
- R1 corresponding to the radical ethyl, propyl, butyl, 2 or 3 methyl-butyl, 2 ethyl-hexyl, is preferred.
- G1, G2, G3, G4, G5 are independently of each other, the remains of an ose selected from hexoses, arabinose and xylose
- A, b, c, d and e being equal to 0 or 1, the sum of a, b, c, d and e being at least equal to 1 arabinosides and alkyl xylosides then representing at least 65% by weight of all the compounds of formula (1). ii) from 1 to 20% by weight of the composition of at least one compound of formula (2) or a salt thereof,
- R2 is a radical chosen from: -CH3, - (CH2) 3-NH- C (NH) -NH2, -CH2-CO-NH2, -CH2-CO-OR3, -CH2-SH - (CH 2) 2 -CO-NH 2, - (CH 2) 2 -CO-OR 3, H, -CH 2 - (C 3 H 3 N 2), -CH (CH 3) -CH 2 -CH 3, -CH 2 -CH (CH 3) -CH 3, - (CH2) 4-NH2, - (CH2) 2-S-CH3, -CH2-C6H5, -CH2-OH, -CH (OH) -CH3, -CH2- (C8H6N), -CH2- (C6H4) - OH, -CH (CH3) -CH3
- R2 is the following cyclic radical: - (CH2) 2 -Y-, Y represents a methylene group -CH2- linked to X
- R3 being optionally identical to R1, is a linear or branched, saturated or unsaturated hydrocarbon radical having from 1 to 4 ethylenic unsaturations, having from 2 to 10 carbon atoms,
- R3 corresponding to ethyl, propyl, butyl, 2 or 3 methyl-butyl, 2-ethylhexyl is preferred.
- R2 represents several radicals as defined above identical or different from each other. and in that they have a foam volume of less than 50 ml and a stability of the foam at 20 minutes of less than 10% according to the Ross Miles test of standard NF-T-73-404 carried out at 50.degree. demineralised water solution comprising 0.1% by weight of composition as described above.
- compositions of the invention also have remarkable emulsifying properties, especially in the presence of electrolytes.
- An emulsion is a dispersion of a liquid in another immiscible liquid.
- the compositions of the invention make it possible to obtain stable emulsions (that is to say having no phase shift after three months of aging at 45 ° C.) even using less than 5% by weight of emulsifying composition with respect to total weight of the emulsion and even when the emulsion contains more than 0.3% by weight of salts relative to the total weight of emulsion.
- the stable emulsions thus obtained will not contain any polymer or chelating agent.
- the emulsifying power of the compositions according to the invention will be evaluated by the method described in standard NF T 73409.
- This method consists in preparing emulsions, which may comprise increasing salt levels (NaCl), by mixing at 70 ° C. at 4% by weight of emulsifying composition relative to the total weight of the emulsion, 15 to 18% by weight of oil relative to the total weight of the emulsion and 81% by weight of water demineralized with respect to the total weight of the emulsion.
- the emulsions are made by vigorous stirring (8000 rpm) using a mechanical stirrer for one minute. They are then put to rest for 15 hours at 20 ° C.
- the emulsions are considered stable if a phase separation of less than 5% relative to the total volume of the emulsion is observed after 30 minutes of centrifugation at 4,000 G, ie a residual emulsion volume of 95%.
- compositions according to the invention characterized in that they comprise: i) from 80 to 99% by weight of the composition of a mixture of compounds of formula
- R 1 is a linear or branched, saturated or unsaturated hydrocarbon radical having from 1 to 4 ethylenic unsaturations, having from 8 to 36 carbon atoms,
- R 1 corresponding to the dodecyl, tetradecyl, hexadecyl and octadecyl radical is preferred.
- G1, G2, G3, G4, G5 are independently of each other, the remains of an ose selected from hexoses, arabinose and xylose
- A, b, c, d and e being equal to 0 or 1, the sum of a, b, c, d and e being at least equal to 1 arabinosides and alkyl xylosides then representing at least 25% by weight of all the compounds of formula (1). ii) from 1 to 20% by weight of the composition of at least one compound of formula (2) or a salt thereof,
- R2 is a radical chosen from: -CH3, - (CH2) 3-NH- C (NH) -NH2, -CH2-CO-NH2, -CH2-CO-OR3, -CH2-SH - (CH 2) 2 -CO-NH 2, - (CH 2) 2 -CO-OR 3, H, -CH 2 - (C 3 H 3 N 2), -CH (CH 3) -CH 2 -CH 3, -CH 2 -CH (CH 3) -CH 3, - (CH2) 4-NH2, - (CH2) 2-S-CH3, -CH2-C6H5, -CH2-OH, -CH (OH) -CH3, -CH2- (C8H6N), -CH2- (C6H4) - OH, -CH (CH3) -CH3
- R2 is the following cyclic radical: - (CH2) 2 -Y-, Y represents a methylene group -CH2- linked to X R3, being optionally identical to R1, is a linear or branched, saturated or unsaturated hydrocarbon radical having from 1 to 4 ethylenic unsaturations, having from 8 to 36 carbon atoms,
- R3 corresponding to the dodecyl, tetradecyl and hexadecyl radical, of octadecyl, is preferred.
- n is an integer greater than or equal to 1; and when n is greater than 1, then R2 represents several radicals as defined above identical or different from each other.
- compositions having emulsifying properties improved with respect to the APGs of the state of the art, in the form of self-emulsifiable base will be used.
- self-emulsifiable is intended to mean a composition which makes it possible to obtain a water-in-oil or oil-in-water emulsion by simple mixing with moderate stirring at hot (between 40 and 80 ° C.) or at cold temperature (at a temperature below 40 ° C.), with an aqueous phase.
- Selfemulsifiable compositions will be obtained by solubilization of a composition of the invention in an appropriate polar phase (mass ratio compositions / polar phase of between 1/100 and 1) such as a polar organic solvent such as formamide, dimethylformamide or a branched fatty alcohol such as Guerbet alcohols of the Isofol type marketed by Sasol, or in an oil by agitation, in particular mechanical or by sonication.
- an appropriate polar phase mass ratio compositions / polar phase of between 1/100 and 1
- a polar organic solvent such as formamide, dimethylformamide or a branched fatty alcohol such as Guerbet alcohols of the Isofol type marketed by Sasol
- an oil by agitation, in particular mechanical or by sonication.
- compositions according to the invention are preferably characterized in that they comprise: i) from 4 to 58% by weight of the composition of a mixture of compounds of formula (1)
- R 1 is a linear or branched, saturated or unsaturated hydrocarbon radical having from 1 to 4 ethylenic unsaturations, having from 8 to 36 carbon atoms,
- R 1 corresponding to the dodecyl, tetradecyl, hexadecyl and octadecyl radical is preferred.
- G1, G2, G3, G4, G5 are independently of each other, the remains of an ose selected from hexoses, arabinose and xylose
- a, b, c, d and e are equal to 0 or 1, the sum of a, b, c, d and e being at least 1 the arabinosides and alkyl xylosides then representing at least 25% by weight of all the compounds of formula (1). ii) from 0.1 to 12% by weight of the composition of at least one compound of formula (2) or a salt thereof,
- R2 is a radical chosen from: -CH3, - (CH2) 3-NH- C (NH) -NH2, -CH2-CO-NH2, -CH2-CO-OR3, -CH2-SH - (CH 2) 2 -CO-NH 2, - (CH 2) 2 -CO-OR 3, H, -CH 2 - (C 3 H 3 N 2), -CH (CH 3) -CH 2 -CH 3, -CH 2 -CH (CH 3) -CH 3, - (CH2) 4-NH2, - (CH2) 2-S-CH3, -CH2-C6H5, -CH2-OH, -CH (OH) -CH3, -CH2- (C8H6N), -CH2- (C6H4) - OH, -CH (CH3) -CH3
- R2 is the following cyclic radical: - (CH2) 2 -Y-, Y represents a methylene group -CH2- linked to X
- R3 being optionally identical to R1, is a linear or branched, saturated or unsaturated hydrocarbon radical having from 1 to 4 ethylenic unsaturations, having from 8 to 36 carbon atoms,
- R3 corresponding to the dodecyl, tetradecyl, hexadecyl or octadecyl radical is preferred.
- n is an integer greater than or equal to 1; and when n is greater than 1, then R2 represents several radicals as defined above identical or different from each other. iii) from 30 to 95.9% by weight of the composition of at least one compound of formula
- R 4 is a linear or branched, saturated or unsaturated hydrocarbon radical having from 1 to 4 ethylenic unsaturations, having from 1 to 36 carbon atoms and more particularly having from 8 to 20 carbon atoms.
- R4 may be different or identical to R1 and R3.
- R4 are alkyl radicals and particularly those derived from primary or secondary alcohols having from 1 to 36 carbon atoms.
- alkyl radicals are methyl, ethyl, butyl and octyl radicals as well as radicals derived from capric, lauric, myristic, palmitic and stearic alcohols.
- Alkyl radicals derived from Guerbet alcohols or technical alcohols derived from the hydrogenation of aldehydes of petrochemical origin can also be selected.
- compositions according to the invention exhibit improved biodegradability compared to the alkyl glycosides of the state of the art.
- the ultimate biodegradability test results can be taken from OECD 301 tests (A, B, C, D, E and F).
- the Biological Oxygen Demand (BOD) that is determined using a closed respirometer.
- a measured volume of mineral medium containing both bacteria from sludge from a domestic wastewater treatment plant and a known concentration of test substance as the sole nominal source of organic carbon, is agitated in a closed bottle at 20 ° C. for 28 days.
- the microorganisms consume oxygen and produce carbon dioxide absorbed by natron (Na 2 CO 3 ), which causes a drop in the pressure in the container.
- This decrease in pressure is detected by a manometer that triggers the production of oxygen by electrolysis.
- the electrolysis is interrupted and the amount of electricity used measured by the monitor. This quantity of electricity is proportional to the quantity of oxygen consumed (mg / mg of product). This is recorded over time by a computer.
- Theoretical Oxygen Demand (DthO) calculated from the raw formula of the product. This is the total amount of oxygen needed to achieve oxidation complete with a chemical and is expressed in mg of oxygen required per mg of test substance. It is calculated from the molecular formula by applying Equation (A) where H, C, Cl, N, S, P, Na and O represent the number of each of these atoms in one mole of product.
- DthO 16 ⁇ (2xC + 0.5x (H-Cl-3xN) + 3xS + 2.5xP + 0.5xNa- ⁇ )
- a respirometer makes it possible to follow the biodegradability of the products as well as that of the chosen control, sodium acetate.
- the pH in the reactors at the end of the handling is between 6 and 8.5; Product degradation is greater than 60% within 10 days as soon as 10% of biodegradability is reached and maximum within 28 days according to the standard.
- compositions of the present invention allow the formulation of surfactants and detergent, agrochemical or cosmetic products. That is to say, it is advantageous to formulate any product allowing the cleaning or wetting of the surface of a solid object or a part of the body following a process involving a physicochemical action other than the simple dissolution of soiling with the compositions of the invention.
- a final aspect of the invention therefore relates to detergent, cosmetic or agrochemical products, characterized in that they contain from 0.1% to 50% by weight of specific base of formulation (detergent base, cosmetic or agrochemical) and 1 99% by weight of surfactant composition according to the invention.
- formulation adjuvants such as those described in "Detergents and Body Care Products” by L. Ho Tan Ta ⁇ , Paris 1999, will be chosen as detergent base or cosmetic base.
- these adjuvants there may be mentioned, for example: thickeners , ionic gelling agents, or nonionic, such as cellulose derivatives (carboxymethylcellulose, hydroxyethylcellulose), guar (hydroxypropylguar, carboxymethylguar, carboxymethylhydroxypropylguar ...), carob, tree exudates (gum arabic, karaya ...
- marine algae extracts (alginates, carrageenates ...), exosudates of microorganisms (xanthan gum), hydrotropic agents, such as short C2-C8 alcohols, in particular ethanol, diols and glycols such as diethylene glycol, dipropylene glycol, skin moisturizers or humectants such as glycerol, sorbitol, collagen, gelatin, aloe vera, hyaluronic acid, urea or skin-protecting agents, such as proteins or protein hydrolysates, cationic polymers, such as cationic guar derivatives (Jaguar C13S®, Jaguar C 162®, Hicare 1000® sold by Rhodia), glycolipids such as sophoroses lipids, fillers such as powders or mineral particles such as calcium carbonate, mineral oxides in the form of powder or in colloidal form (particles of smaller size or of the order of a micrometer, sometimes of a few tens of nanometers) such as
- photoprotective mineral monopigers such as titanium dioxide or cerium oxides in the form of powder or colloidal particles, softeners, antioxidants, self-tanning agents such as dihydroxyacetone, repellents against insects, vitamins, perfumes, fillers, sequestering agents, dyes, buffering agents, abrasives such as ground apricot kernels, microbeads, polyphosphates (tripolyphosphates, pyrophosphates) orthophosphates, hexametaphosphates) of alkali metals, ammonium or alkanolamines, tetraborates or borate precursors, silicates, in particular those having a SiO 2 / Na 2 O ratio of the order of 1.6 / 1 to 3.2 / 1 and the lamellar silicates described in US-A -4 664 839, the al
- anti-redeposition agents such as: ethoxylated monoamines or polyamines, ethoxylated amine polymers (US-A-4) 597,898, EP-A-1 984), carboxymethylcellulose, sulfonated polyester oligomers obtained by condensation of isophthalic acid e, dimethyl sulphosuccinate and diethylene glycol (FR-A-2,236,926), polyvinylpyrrolidones, chelating agents of iron and magnesium, such as: nitrilotriacetates, ethylenediaminetetraacetates, hydroxyethylethylenediaminetriacetates, nitrilotris- (methylenephosphonates) polyfunctional aromatic compounds such as dihydroxydisulfobenzenes, fluorescent agents such as stilbene derivatives, pyrazoline, coumarin, fumaric acid, cinnamic acid, azoles, methinecyanines, thiophenes, foam suppressants such as:
- the invention finally relates to emulsions which comprise by weight: a. from 0.1 to 20% relative to the total weight of the emulsion, of the composition according to the invention, and preferably from 1 to 10% b. from 0 to 95% relative to the total weight of the emulsion, of oil, and preferably between 0 and 50% c. from 0 to 50% relative to the total weight of the emulsion, active substance, and preferably between 0 and 20% d. water in addition to 100%.
- the emulsions prepared from the compositions of the invention can be used in various cosmetic or dermatological or industrial applications, for example in the form of creams for the face, for the body, for the scalp or for the hair or in the form of milk. for the body or for removing make-up or in the form of ointments for example for pharmaceutical use or finally in the road industry for the preparation of road surfaces.
- These emulsions can also be used for makeup, especially in the form of foundation, after addition of pigments. They can also be used as sunscreens after addition of UVA and / or UVB and / or DHA filters, or as creams or milks after sun after addition of soothing compounds such as panthenol or shea butter.
- the emulsions may also contain surfactants, foaming or ionic or nonionic detergents such as sodium lauryl ether sulphate, alkyl betaines to make washing emulsions such as moisturizing washing creams, or emulsions for shaving.
- surfactants foaming or ionic or nonionic detergents such as sodium lauryl ether sulphate, alkyl betaines to make washing emulsions such as moisturizing washing creams, or emulsions for shaving.
- the emulsions may further contain, in order to increase their cosmetic qualities, a cosmetic wax such as, for example, rice wax, candelilla wax, Japanese wax or wheat straw wax.
- a cosmetic wax such as, for example, rice wax, candelilla wax, Japanese wax or wheat straw wax.
- compositions of the invention can also be used in formulations where it is necessary to maintain in suspension in water finely divided solids, such as agrochemical active ingredient formulations (herbicides, insecticides, fungicides, etc.) or bitumen, known under the generic name of "concentrated suspensions".
- agrochemical active ingredient formulations herein, insecticides, fungicides, etc.
- bitumen known under the generic name of "concentrated suspensions”.
- concentration suspensions such as, for example, a wetting surfactant, taken from the alkylated derivatives of aliphatic alcohols, the aryl sulphonated derivatives, are found as additives in a concentrated suspension formulation.
- dispersing polymers such as polyacrylic acids and their salts, anhydride (or acid) maleic-diisobutylene copolymers and their salts, condensed sodium methylnaphthalenesulfonates, lignin-derived dispersing polymers such as sodium or calcium lignosulfonates or other dispersing surfactants such as alkoxylated derivatives, optionally sulphated or phosphated with tristyrylphenols.
- dispersing polymers such as polyacrylic acids and their salts, anhydride (or acid) maleic-diisobutylene copolymers and their salts, condensed sodium methylnaphthalenesulfonates, lignin-derived dispersing polymers such as sodium or calcium lignosulfonates or other dispersing surfactants such as alkoxylated derivatives, optionally sulphated or phosphated with tristyrylphenols.
- these formulations may contain antifreeze additives such as propylene glycol and thickening additives which modify the rheological behavior of the suspension, such as xanthan gum, cellulose derivatives (carboxymethylcellulose), guar gum or its derivatives, clays or modified clays such as bentonite and bentones.
- antifreeze additives such as propylene glycol and thickening additives which modify the rheological behavior of the suspension, such as xanthan gum, cellulose derivatives (carboxymethylcellulose), guar gum or its derivatives, clays or modified clays such as bentonite and bentones.
- the oily phase of the emulsions according to the invention may consist of the linear or branched fatty alcohol or alcohols which may be present in the emulsifying composition of the invention without it being necessary to use another oil. But more generally we will use an oil or a mixture of oils, chosen without the intention to be limited to, among the following oils:
- Vegetable oils such as sweet almond oil, coconut oil, castor oil, jojoba oil, olive oil, rapeseed oil, hazelnut oil, palm oil, shea butter, apricot kernel oil, calophylum oil, safflower oil, avocado oil, walnut oil, lemon oil grape seed oil, wheat germ oil, sunflower oil, corn germ oil, soybean oil, cottonseed oil, alfalfa oil, oil of barley, poppy oil, pumpkin oil, sezame oil, rye oil, evening primrose oil, passionflower oil, derivatives of these oils such as hydrogenated oils ,
- Oils of animal origin such as tallow oil, fish oil,
- Mineral oils such as liquid paraffin, liquid petroleum jelly and mineral oils especially from petroleum cuts,
- Synthetic oils such as poly- ⁇ -olefins
- Alkanediols having from 2 to 10 carbon atoms such as 1,2 propanediol, 1,3-butanediol,
- Alcohols having a saturated or unsaturated aliphatic radical having 1 to 4 ethylenic unsaturations, linear or branched, having 12 to 22 carbon atoms such as myristic alcohol, cetyl alcohol, stearyl alcohol, oleic alcohol , Polyethylene glycols or polypropylene glycols,
- Fatty esters such as alkyl myristates, especially butyl myristate, propyl myristate, alkyl palmitates such as isopropyl palmitate, alkyl stearates, in particular hexadecyl stearates, alkyl oleates , especially dodecyl oleate, alkyl laurates, especially hexyl laurate, propylene glycol dicaprylate, 2-ethylhexyl cocoate, esters of lactic acid, behenic acid , isostearic acid such as isostearyl isostearate, fatty acid esters of rapeseed, sunflower fatty acids, linseed fatty acids, cotton fatty acids, soy,
- Silicone oils comprising cyclic polydimethylsiloxanes, ⁇ - ⁇ hydroxylated polydimethylsiloxanes, ⁇ - ⁇ trimethylsilylated polydimethylsiloxanes, polyorganosiloxanes such as polyalkylmethylsolixanes, polymethylphenylsiloxanes, polydiohismelsiloxanes, amino derivatives of silicones, silicone copolyethers or mixed derivatives of silicones such as mixed polyalkylmethylsiloxane-silicone copolyether copolymers.
- the emulsions will comprise, as active substance, specific agents according to the application envisaged (cosmetics, textiles, industrial cleaning, household products, road industry) such as anti-scale, alkaline, bleaching agents, enzymes, polymers (or thickening agent). ), anti-foam agents or foam promoters, optical brighteners, opacifiers, dyes, various fillers for adjusting the pH, flavors, preservatives or therapeutic or touching agents, and especially the formulation adjuvants mentioned previously.
- agents such as anti-scale, alkaline, bleaching agents, enzymes, polymers (or thickening agent).
- anti-foam agents or foam promoters such as anti-scale, alkaline, bleaching agents, enzymes, polymers (or thickening agent).
- anti-foam agents or foam promoters such as anti-scale, alkaline, bleaching agents, enzymes, polymers (or thickening agent).
- anti-foam agents or foam promoters such as anti-scale, alkaline,
- the emulsions may be manufactured either by directly mixing the solid or liquid ingredients at a temperature of between room temperature and 200 ° C. and by homogenizing the preparation by vigorous stirring or by means of a high-pressure homogenizer, or by preparing independently the lipophilic and hydrophilic phases at a temperature between room temperature and 90 ° C and homogenizing the preparation by adding one of the phases on the other with stirring.
- the following examples illustrate the invention, without limiting it:
- EXAMPLE 1 Surfactant composition according to the invention comprising decyl glycosides derived from desamylated wheat bran and a decyl ester of L-Proline
- a surfactant composition No. 1 is prepared by dissolving L-Proline decyl ester (PRO ClO) and decyl glycosides derived from the desamylated wheat bran (APP ClO).
- PRO ClO is obtained by esterification of decanol with proline in the presence of a catalytic amount of methanesulfonic acid according to a protocol adapted from J. Biol. Chem. 161, 259-269, 1945.
- APP ClO is a mixture of alkyl glycosides obtained by grafting decanol onto a syrup of pentoses obtained according to the method described in Example 1 of application FR 2723858. The main components are described below. Their proportion is determined by gas chromatography.
- Decyl glucosides correspond to the compounds of formula (1) in which R 1 is a decyl radical, Gl is the rest of glucose, a is equal to 1 and b, c, d and e are equal to 0.
- Decyl xylosides correspond to the compounds of formula (1) in which R 1 is a decyl radical, Gl is the residue of xylose, a is equal to 1 and b, c, d and e are equal to 0.
- Decyl arabinosides correspond to the compounds of formula (1) in which R 1 is a decyl radical, Gl is the rest of arabinose, a is equal to 1 and b, c, d and e are equal to 0.
- the other glycosides correspond to the polyglycosides of formula (1) where R 1 is the decyl radical and the sum a, b, c, d, e is greater than or equal to 2.
- composition No. liters by weight relative to the dry matter the following proportions.: Components / dry matter% by weight
- EXAMPLE 2 Surfactant composition according to the invention comprising dodecyl and tetradecyl glycosides derived from desamylated wheat bran and alcoholic esters of amino acids.
- compositions according to the invention comprising dodecyl and tetradecyl glycosides (APP C12 / C14), dodecyl and tetradecyl amino acid esters (C12 / C14 AAE) are prepared.
- APP C 12 / Cl 4 is a mixture of alkyl glycosides obtained by grafting a mixture of dodecyl alcohol and tetradecyl alcohol (LOROL 1214S from the company COGNIS) on a syrup of pentoses obtained according to the method described in Example 1 of the application FR 2723858.
- the proportion of each main constituent is determined by gas chromatography.
- AAE C 12 / Cl 4 is obtained by esterification of a mixture of dodecyl alcohol and tetradecyl alcohol (LOROL 1214S from the company COGNIS) with a mixture of amino acids derived from the hydrolysis of wheat gluten in the presence of a catalytic amount of sulfuric acid according to the protocol of J. Biol. Chem. 161, 259-269, 1945 applied to a mixture of amino acids.
- LOROL 1214S from the company COGNIS
- the dodecyl glucosides correspond to the compounds of formula (1) in which R 1 is a dodecyl radical, Gl is the rest of the glucose, a is equal to 1 and b, c, d and e are equal to O.
- Tetradecyl glucosides correspond to the compounds of formula (1) in which R 1 is a tetradecyl radical, Gl is the rest of glucose, a is equal to 1 and b, c, d, and e are equal to O.
- the dodecyl xylosides correspond to the compounds of formula (1) in which R1 is a dodecyl radical, Gl is the residue of xylose, a is equal to 1 and b, c, d and e are equal to O.
- Tetradecyl xylosides correspond to the compounds of formula (1) in which R 1 is a tetradecyl radical, G 1 is the residue of xylose, a is 1 and b, c, d and e are equal to 0.
- the dodecyl arabinosides correspond to the compounds of formula (1) in which R 1 is a dodecyl radical, Gl is the rest of arabinose, a is equal to 1 and b, c, d and e are equal to 0.
- Tetradecyl arabinosides correspond to the compounds of formula (1) in which R 1 is a tetradecyl radical, Gl is the rest of arabinose, a is equal to 1 and b, c, d and e are equal to 0.
- composition No. 2 is then obtained having, by weight relative to the dry matter, the following proportions:
- composition no. 3 according to the invention 325 g of composition no. 3 according to the invention are obtained, which is dissolved in demineralized water until a solution of 30% by weight of dry matter is obtained. After bleaching with hydrogen peroxide, a composition having the following characteristics is obtained:
- the proportion of each alkyl glycoside is determined by gas chromatography.
- octyl glucosides correspond to the compounds of formula (1) in which R1 is an octyl radical, Gl is the rest of the glucose, a is equal to 1 and b, c, d and e are equal to 0.
- Decyl glucosides correspond to the compounds of formula (1) in which R 1 is a decyl radical, Gl is the rest of glucose, a is equal to 1 and b, c, d and e are equal to 0.
- Octyl xylosides correspond to the compounds of formula (1) in which R1 is an octyl radical, Gl is the residue of xylose, a is equal to 1 and b, c, d and e are equal to 0.
- Decyl xylosides correspond to the compounds of formula (1) in which R 1 is a decyl radical, Gl is the residue of xylose, a is equal to 1 and b, c, d and e are equal to 0.
- Octyl arabinosides correspond to the compounds of formula (1) in which R1 is an octyl radical, G1 is the rest of arabinose, a is equal to 1 and b, c, d and e are equal to 0.
- Decyl arabinosides correspond to the compounds of formula (1) in which R 1 is a decyl radical, Gl is the rest of arabinose, a is equal to 1 and b, c, d and e are equal to 0.
- composition No. 4 310 g of surfactant composition No. 4 are obtained which are dissolved in demineralized water until a solution of 30% by weight of dry matter is obtained. After bleaching with hydrogen peroxide, a composition having the following characteristics is obtained:
- the proportion of each alkyl glycoside is determined by gas chromatography. Components% by weight
- octyl glucosides correspond to the compounds of formula (1) in which R1 is an octyl radical, Gl is the rest of the glucose, a is equal to 1 and b, c, d and e are equal to 0.
- Decyl glucosides correspond to the compounds of formula (1) in which R 1 is a decyl radical, Gl is the rest of glucose, a is equal to 1 and b, c, d and e are equal to 0.
- Octyl xylosides correspond to the compounds of formula (1) in which R1 is an octyl radical, Gl is the residue of xylose, a is equal to 1 and b, c, d and e are equal to 0.
- Decyl xylosides correspond to the compounds of formula (1) in which R 1 is a decyl radical, Gl is the residue of xylose, a is equal to 1 and b, c, d and e are equal to 0.
- Octyl arabinosides correspond to the compounds of formula (1) in which R1 is an octyl radical, G1 is the rest of arabinose, a is equal to 1 and b, c, d and e are equal to 0.
- Decyl arabinosides correspond to the compounds of formula (1) in which R 1 is a decyl radical, Gl is the rest of arabinose, a is equal to 1 and b, c, d and e are equal to 0.
- the proportion of each alkyl glycoside is determined by gas chromatography.
- octyl glucosides correspond to the compounds of formula (1) in which R1 is an octyl radical, Gl is the rest of the glucose, a is equal to 1 and b, c, d and e are equal to 0.
- Decyl glucosides correspond to the compounds of formula (1) in which R 1 is a decyl radical, Gl is the rest of glucose, a is equal to 1 and b, c, d and e are equal to 0.
- Octyl xylosides correspond to the compounds of formula (1) in which R1 is an octyl radical, Gl is the residue of xylose, a is equal to 1 and b, c, d and e are equal to 0.
- Decyl xylosides correspond to the compounds of formula (1) in which R 1 is a decyl radical, Gl is the residue of xylose, a is equal to 1 and b, c, d and e are equal to 0.
- Octyl arabinosides correspond to the compounds of formula (1) in which R1 is an octyl radical, G1 is the rest of arabinose, a is equal to 1 and b, c, d and e are equal to 0.
- Decyl arabinosides correspond to the compounds of formula (1) in which R 1 is a decyl radical, Gl is the rest of arabinose, a is equal to 1 and b, c, d and e are equal to 0.
- EXAMPLE 6 Process for preparing a surfactant composition according to the invention.
- the proportion of each alkyl glycoside is determined by gas chromatography.
- Hexadecyl glucosides correspond to the compounds of formula (1) where R1 is hexadecyl, Gl is the rest of glucose, a is 1 and b, c, d, and e are 0.
- Octadecyl glucosides correspond to the compounds of formula (1) in which R 1 is an octadecyl radical, Gl is the rest of glucose, a is equal to 1 and b, c, d, and e are equal to 0.
- hexadecyl xylosides correspond to the compounds of formula (1) in which R 1 is a hexadecyl radical, Gl is the residue of xylose, a is 1 and b, c, d and e are 0.
- Octadecyl xylosides correspond to the compounds of formula (1) in which R 1 is an octadecyl radical, G 1 is the residue of xylose, a is equal to 1 and b, c, d and e are equal to 0.
- Hexadecyl arabinosides correspond to the compounds of formula (1) where R1 is a hexadecyl radical, G1 is the rest of arabinose, a is 1 and b, c, d, and e are 0.
- Octadecyl arabinosides correspond to the compounds of formula (1) in which R1 is an octadecyl radical, G1 is the rest of arabinose, a is equal to 1 and b, c, d, and e are equal to 0.
- composition No. 7 35 g of surfactant composition No. 7 are obtained, which is dissolved in demineralised water until a solution of 64.5% by weight of dry matter is obtained. After bleaching with hydrogen peroxide, a composition having the following characteristics is obtained:
- each alkyl glycoside is determined by gas chromatography.
- Amyl glucosides correspond to the compounds of formula (1) where R1 is a 2 or 3 methylbutyl radical, Gl is the rest of glucose, a is equal to 1 and b, c, d, and e are equal to 0.
- Amyl xylosides correspond to the compounds of formula (1) where R1 is a 2 or 3 methylbutyl radical, Gl is the residue of xylose, a is equal to 1 and b, c, d, and e are equal to 0.
- Amyl arabinosides correspond to the compounds of formula (1) in which R1 is a 2 or 3 methyl-butyl radical, G1 is the rest of arabinose, a is equal to 1 and b, c, d and e are equal to 0.
- the surfactant solutions were made with ultra-permuted water.
- composition No. 1 according to the invention has an efficiency and stability greater than APP ClO at low concentrations.
- EXAMPLE 9 Foaming Power of Composition No. 2
- the foaming properties are determined using a foaming power test according to the French standard NF-T-73-404 of November 1966.
- the foam volumes are measured at 50 ° C. of the solutions to be studied and the foaming stability is also determined at 20 minutes.
- a solution comprising, by weight, 99.9% of demineralised water and 0.1% of composition No. 2 is prepared.
- a solution comprising, by weight, 99% of demineralized water and 0.1% of APP C12 / C14 glycosides described in Example No. 2 is also prepared.
- surfactant compositions according to the invention have superior foaming properties and foaming stability to dodecyl and tetradecyl glycoside surfactants not containing amino acid derivatives (APP C 12 / Cl 4).
- EXAMPLE 10 Emulsifying Properties of Composition No. 2
- An emulsion is prepared by mixing, at 70 ° C., 1.5 g of emulsifying composition of Example No. 2, 3.75 g of oil (Miglyol 812N fatty acid triglycerides marketed by Hiils), and 19.75 g of osmosis water.
- the emulsion is made by vigorous stirring (8000 rpm) using a mechanical stirrer for one minute. It is then rested for 15 hours at 20 ° C.
- the stability of the emulsion is evaluated by determining the residual emulsion volume relative to the total volume after 30 minutes of centrifugation at 4000G.
- composition No. 2 The emulsion produced from composition No. 2 is 100% stable after centrifugation.
- EXAMPLE 11 Surfactant Properties of the Compositions Nos. 3, 4 and 5
- the critical micellar concentration and the C20 are measured for each composition by the Wilhelmy blade technique at 25 ° C.
- the critical micellar concentrations (CMC) and C20 as well as the surface tensions were determined at 25 ° C. using a K100 tensiometer marketed by KRUSS.
- the surfactant solutions were made with ultra-permuted water.
- the CMC, C20 and surface tension of a solution of alkyl glycosides obtained according to Example 1 of the application FR 2723858 will also be measured by way of comparison.
- the wetting power is appreciated by measuring the wetting time of a cotton disc placed within a solution of surfactants at a defined concentration. 700 ml of a test solution containing 1 g / l of surfactant material in distilled water are placed in a beaker at a temperature of 25 ° C. The wetting time is determined experimentally with the aid of a stopwatch. Ten consecutive measurements were made with the same solution while taking care however to discard the used cotton discs after each measurement.
- the comparative examples are carried out with glycosides having the same fatty chain from octanol and decanol (APP C8 / C10) and having not more than 0.5% of nitrogen according to the Kjeldhal method, and obtained according to US Pat. example No. 1 of the patent FR 2723858 (or Dl) Components / dry matter% by weight
- octyl glucosides correspond to the compounds of formula (1) in which R1 is an octyl radical, Gl is the rest of the glucose, a is equal to 1 and b, c, d and e are equal to 0.
- Decyl glucosides correspond to the compounds of formula (1) in which R 1 is a decyl radical, Gl is the rest of glucose, a is equal to 1 and b, c, d and e are equal to 0.
- Octyl xylosides correspond to the compounds of formula (1) in which R1 is an octyl radical, Gl is the residue of xylose, a is equal to 1 and b, c, d and e are equal to 0.
- Decyl xylosides correspond to the compounds of formula (1) in which R 1 is a decyl radical, Gl is the residue of xylose, a is equal to 1 and b, c, d and e are equal to 0.
- Octyl arabinosides correspond to the compounds of formula (1) in which R1 is an octyl radical, G1 is the rest of arabinose, a is equal to 1 and b, c, d and e are equal to 0.
- Decyl arabinosides correspond to the compounds of formula (1) in which R 1 is a decyl radical, Gl is the rest of arabinose, a is equal to 1 and b, c, d and e are equal to 0.
- Emulsions containing possibly increasing levels of salt are prepared by mixing at 70 ° C., 0.75 g of emulsifying composition (I g in the case of sunflower oil), 3.75 g of oil ( Miglyol 812N fatty acid triglycerides marketed by H ⁇ ls / sunflower oil / Dimethicone), and 20.375 g (20.125 g for sunflower oil) of osmosis water with varying amounts of salt.
- the emulsions are made by vigorous stirring (8000 rpm) using a mechanical stirrer for one minute. They are then put to rest for 15 hours at 20 ° C.
- the stability of the emulsions is evaluated by determining the residual emulsion volume relative to the total volume after 30 minutes of centrifugation at 4000G.
- a comparative example is carried out with a self-emulsifying composition equivalent to composition No. 6 but not containing amino acid derivatives, as APP C 16 / Cl 8.
- This composition is obtained by glycosylation of a mixture of hexadecanol and octadecanol with D-xylose according to the protocol of example 4 of patent EP 1027921. This protocol was applied at a xylose / fatty alcohol molar ratio to obtain a composition as described below.
- hexadecyl xylosides correspond to the compounds of formula (1) in which R 1 is a hexadecyl radical, Gl is the residue of xylose, a is 1 and b, c, d and e are 0.
- Octadecyl xylosides correspond to the compounds of formula (1) in which R 1 is an octadecyl radical, G 1 is the residue of xylose, a is equal to 1 and b, c, d and e are equal to 0.
- the emulsions are produced with proportions relative to the total weight of the emulsion of 3 to 4% of self-emulsifying base, ie 0.29 to 0.38% of surfactants (pentosides for APP C 16 / Cl 8 and pentosides and amino acid esters for composition No. 6).
- the foaming properties are determined using a foaming power test according to the French standard NF-T-73-404 of November 1966.
- a solution comprising, by weight, 99.9% of deionized water and 0.1% of composition No. 7 is prepared.
- Composition No. 3 76.6 Readily biodegradable
- composition No. 4 66 Readily biodegradable
- composition No. 5 66 Readily biodegradable
- the lipophilic phase (10 g of isostearyl isostearate from Gattefossé) which contains 4 g of composition No. 2 of Example 2 and the hydrophilic phase (86 g of osmosis water) are separately heated to a temperature of 7O 0 C.
- the lipophilic phase is stirred vigorously using a mechanical stirrer (800 rpm) and thereto was added in 2 minutes the hydrophilic phase until the phase inversion characterized by an abrupt change viscosity. The addition can then be faster (1 minute).
- the emulsion is allowed to cool with slow stirring (300 rpm) to a temperature of the order of 25 ° C.
- composition No. 6 of Example 6 70 g of rapeseed oil of the company OLEON and 27 g of water osmosed at the same time at a temperature of 75 ° C. are heated and then allowed to homogenize (10,000 rpm) at the same temperature for 2 minutes and finally allowed to cool with slow stirring (300 rpm) to a temperature of about 25 0 C. This emulsion remains stable for 2 months in a drying oven. 45 ° C.
- EXAMPLE 18 Preparation of a Concentrated Phytosanitary Emulsion from Composition According to the Invention
- composition No. 6 of Example 6 70 g of rapeseed methyl ester (from the company OLEON) and 26 g of water osmosed at the same time at a temperature of 75 ° C. are heated and then homogenized. using a mechanical stirrer (10000 rpm) at the same temperature for 2 minutes and finally allowed to cool with slow stirring (300 rpm) to a temperature of about 25 ° C. This emulsion remains stable for 2 months in an oven at 45 ° C.
- Aloe vera 1 0%
- EXAMPLE 23 Liquid detergent composition from a composition according to the invention
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Abstract
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Application Number | Priority Date | Filing Date | Title |
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FR0701995A FR2913896B1 (fr) | 2007-03-20 | 2007-03-20 | Nouvelles compositions a base de glycosides d'alkyle, procede pour leur preparation et utilisation comme agent tensioactifs |
PCT/FR2008/000315 WO2008135646A1 (fr) | 2007-03-20 | 2008-03-11 | Nouvelles compositions a base de glycosides d'alkyle, procede pour leur preparation et utilisation comme agents tensioactifs |
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FR2928376B1 (fr) * | 2008-03-06 | 2011-05-20 | Agro Ind Rech S Et Dev | Compositions detergentes a base de polyglucosides d'alkyle |
FR2942974B1 (fr) * | 2009-03-11 | 2011-03-18 | Agro Ind Rech S Et Dev Ard | Compositions emulsionnantes a base de polyglycosides d'alkyle et d'esters |
FR2959140A1 (fr) * | 2010-04-23 | 2011-10-28 | Agro Ind Rech S Et Dev Ard | Preparations facilitees de vesicules a l'aide des poly-pentosides d'alkyles et utilisations desdites preparations |
FR2971511B1 (fr) * | 2011-02-16 | 2021-09-24 | Colas Sa | Emulsion de liant hydrocarbone constituee d'une dispersion de liant hydrocarbone dans une phase aqueuse, comprenant une composition bio-tensioactive |
FR2981568B1 (fr) * | 2011-10-20 | 2013-12-13 | Lvmh Rech | Composition cosmetique ou dermatologique comprenant des vesicules de polypentoside d'alkyle, et son procede de preparation |
FR3034422B1 (fr) * | 2015-04-03 | 2017-05-19 | Agro Ind Rech Et Dev (Ard) | Procede ameliore pour la production de compositions a base de polyglucosides d'alkyle a partir de biomasse lignocellulosique |
DE102015007403A1 (de) * | 2015-06-08 | 2016-12-08 | Sodasan Wasch- und Reinigungsmittel GmbH | Phosphat- und phosphonatfreies Maschinengeschirrspülmittel |
EP3538629A1 (fr) * | 2016-11-08 | 2019-09-18 | Basf Se | Composition pouvant être utilisée en tant que tensioactif |
CN108685760A (zh) * | 2018-08-01 | 2018-10-23 | 湘南学院 | 一种用于皂基产品的组合物 |
PL3927752T3 (pl) * | 2019-02-22 | 2023-09-18 | Basf Se | Sposób wytwarzania roztworu wiskozy i wytworzony tym sposobem roztwór wiskozy oraz sposób wytwarzania włókna wiskozowego |
CN111848704A (zh) * | 2019-04-24 | 2020-10-30 | 湘潭大学 | 1,2-顺式醇醚木糖苷表面活性剂及制备方法 |
FR3098218B1 (fr) | 2019-07-01 | 2021-11-26 | Colas Sa | Oligomère biosourcé issu du chitosan et son utilisation comme émulsifiant cationique ou non ionique d’émulsion aqueuse de liants bitumineux ou non bitumineux |
CN110585990B (zh) * | 2019-08-20 | 2021-10-15 | 浙江工业大学 | 一种绿色复合物乳化剂及其制备方法 |
CN113016453A (zh) * | 2021-03-03 | 2021-06-25 | 浙江东郁广陈果业有限公司 | 一种苹果苗圃除草方法 |
WO2023244325A1 (fr) * | 2022-06-13 | 2023-12-21 | Applechem Inc. | Préparations comprenant un polyester de polyols polyalcoxylés biodégradables |
CN118146086B (zh) * | 2024-05-09 | 2024-07-12 | 山东小为生物科技有限公司 | 一种从发酵液中纯化琥珀酸的方法 |
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DE3928063A1 (de) * | 1989-08-25 | 1991-02-28 | Henkel Kgaa | Belaghemmende zahnpaste |
DE4302315A1 (de) * | 1993-01-28 | 1994-08-04 | Henkel Kgaa | Oberflächenaktive Mischungen |
FR2723858B1 (fr) * | 1994-08-30 | 1997-01-10 | Ard Sa | Procede de preparation d'agents tensioactifs a partir de sous-produits du ble et nouveaux xylosides d'alkyle |
FR2744648B1 (fr) * | 1996-02-08 | 1998-03-20 | Ard Sa | Procede de preparation d'agents tensioactifs |
DE19950497B4 (de) * | 1999-10-20 | 2004-12-02 | Cognis Deutschland Gmbh & Co. Kg | Kosmetische und/oder pharmazeutische Zubereitungen und deren Verwendung |
FR2869912B1 (fr) * | 2004-05-04 | 2006-08-04 | Agro Ind Rech S Et Dev A R D S | Nouvelle famille de compositions a base de polyglycosides d'alkyle et de composes derives de la glycine betaine, utilisation comme agent tensioactif |
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