Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
  • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
  • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
  • C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
  • C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
  • C07C229/12—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
  • A01N37/46—N-acyl derivatives
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
  • A23J3/00—Working-up of proteins for foodstuffs
  • A23J3/14—Vegetable proteins
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K38/00—Medicinal preparations containing peptides
  • A61K38/01—Hydrolysed proteins; Derivatives thereof
  • A61K38/011—Hydrolysed proteins; Derivatives thereof from plants
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
  • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
  • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
  • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
  • A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K9/00—Medicinal preparations characterised by special physical form
  • A61K9/0012—Galenical forms characterised by the site of application
  • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
  • A61P31/04—Antibacterial agents
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07K—PEPTIDES
  • C07K4/00—Peptides having up to 20 amino acids in an undefined or only partially defined sequence; Derivatives thereof
  • C07K4/10—Peptides having up to 20 amino acids in an undefined or only partially defined sequence; Derivatives thereof from plants

Definitions

• the present invention relates to lipopolyamino acids consisting of mixtures of N-acylated amino acids, said amino acids obtained by total hydrolysis of proteins, their preparation process and their applications, in particular in pharmaceutical, detergent or food cosmetic compositions.
• Lipopolyamino acids consisting of mixtures of friendly acids and / or peptides obtained by total or partial hydrolysis of proteins, N-acylated by acyl radicals, are well known and used in numerous fields of application.
• French patent application No. 2,403,024 for use in the agricultural field, in particular as a fertilizer, metal salts, peptides or acyl-friendly acids.
• Peptides and amino acids are obtained by partial or total hydrol of animal proteins, mainly kera and collagen. The latter constitute, alongside Telastine and casein, the main sources of animal proteins used to obtain lipopolyamino acids.
• lipopolyamino acids consisting of mixtures of acyl friend acids, or acyl peptides, derived from animal protein hydrolysates, however have the disadvantages of presenting potential risks of contamination by pathogenic agents, such as vir occasionally present in animal tissues. .
• acyl proteins have the drawback of having a low wetting power and foam which is still insufficiently stable, especially in hard water or in the presence of soiling.
• the present invention therefore relates to lipopolyamino acids comprising no potential risks of contamination of humans or animals by pathogenic agents.
• lipopolyamino acids of the invention make it possible to confer significant wetting power as well as obtaining a stable foam even in hard water or in the presence of dirt.
• the present invention therefore relates to lipopolyaminoacids consisting of a mixture of amino acids obtained by total hydrolysis of a protein, said amino acids being, N-acylated by a C - C 3Q acyl radical, characterized in that the protein is made from oilseed meal.
• cake is a mass of coarse powder formed with the residue of certain plants from parts of these plants, such as their seeds, and from which the oil has been expri. Such cakes are usually intended for animal feed or used as fertilizer. These cakes may contain up to 50% by weight, or even more, of proteins and therefore constitute a particularly rich protein source.
• Said proteins can be hydrolyzed while they are still contained in the cake, or before their hydrolysis can be separated from said cake by conventional methods. In the latter case, these proteins can then in particular be in the form of a concentrate whose protein content can reach up to 70% by weight, in the form of an isolate whose protein content can reach 90% by weight or as a purified protein.
• oleaginous plants from which said oil cakes are prepared mention may be made of those belonging to the cruciferous family, such as rapeseed, to the oleaceae family, such as the olive tree or the leguminous family such as lupine, groundnut, or, more advantageously soy.
• lipopolyamino acids of the invention mainly consist of mixtures of N-acylated amino acids, also known under the term “lipoaminoac des", of general formula (I):
• R represents an aliphatic radical in C- - C 2 g, preferably in C, - C, g saturated or unsaturated, linear or branched, and R 'represents the main chain of an amino acid resulting from the total hydrolysis of a protein originating from an oilseed meal.
• the acyl radical chosen from octanoyl, undecylenoyl, lauroyl, coconut palmitoyl, stearoyl, linoleoyl or oleoyl radicals.
• the carboxylic function of the lipoamino acids of formula I can be free or salified.
• the lipopolyamino acids of the invention can be salified with ammonia, alkali metal cations, such as sodium or potassium, or alkaline earth cations, such as calcium or magnesium, or metal cations, such as cobalt, iron, manganese, copper, zinc, aluminum, in particular in the form of monobasic or dibasic aluminum salts.
• They can also be salified with organic bases such as mono, di triethanola ine, lysine, arginine, histidine, Vornithine, choline or morpholine.
• the invention also relates to a method for preparing lipopolyamino acids described above.
• a protein from oil cake from an oilseed plant is completely hydrolyzed in an acid medium so as to obtain a mixture of amino acids, the pH of this mixture is brought to a va of between 8 and 11 by means of a base.
• the amino acids are N-acylated according to a conventional method, and, where appropriate, the N-acylated amino acids are reacted with an inorganic or organic base in order to form a corresponding salt.
• total hydrolysis it is meant in the context of the present invention, that substantially all of the constituent amino acids of the protein are released. Such total hydrolysis can be confirmed by the absence of a biuretic reaction.
• the hydrolysis to can however lead, according to the conditions of implementation, to a mixture of free amino acids comprising a low proportion of oligopeptides; the average chain length of this mixture is about 1.4 or less. Generally, the proportion of these oligopept in said mixture is between 1 and 5% by weight.
• lipopolyamino acids obtained from a mixture comprising free amino acids and oligopeptides form an integral part of the present invention.
• Such a conventional operation can for example consist of a separation on an ion exchange resin.
• the total hydrolysis can be carried out in aqueous solution using a strong acid, such as hydrochloric acid, in particular in a concentration of the order of 25% to 35% by weight.
• a strong acid such as hydrochloric acid
• the temperature at which the hydrolysis is carried out is usually between 6 and 130 ° C.
• the pH of the resulting mixture can be reduced to a pH between 3 and 7, more generally close to 5, by means of a base, such as sodium hydroxide, for a bleaching operation and d filtration, carried out conventionally.
• a base such as sodium hydroxide
• the resulting mixture is generally filtered, in particular with a view to eliminating the carbohydrates constituting said cake.
• N-acylation of the amino acids, and where appropriate of oligopeptides, contained in the mixture resulting from the total hydrolysis, can be carried out by means of derivatives of activated carboxylic acids in C. C 3Q .
• Such activated derivatives are preferably the symmetrical anhydride of these acids or acid chlorides. This operation is generally carried out at a temperature between 0 ° and 100 ° C.
• the lipopolyamino acids thus obtained can be optionally purified or discolored by conventional methods such as crystallization or chromatography.
• Salts of lipopolyamino acids thus prepared can then be obtained by reaction with organic or inorganic bases, or with metallic derivatives. Mention may be made, as organic or inorganic bases, of potash, soda, lime, magnesia, ammonia, onoethanolamine, diethanola ine, triethanolamine, morpholine, histidine, vornithine, lysine, varginine or choline.
• the lipopolyamino acids of the invention can be used in numerous fields of application. They can in particular be used in cosmetic or food composites in which they are generally present in contents of between 0.5 and 20% by weight, more generally between 1 and 10% by weight.
• Such cosmetic compositions can in particular be shampoos, soaps, creams, milks, foams, aerosols, gels, sticks, oils, emulsions, toothpastes or aqueous or alcoholic lotions.
• the lipopolyamino acids of the invention are in particular used as emollients, surfactants and / or regulators of the pH of the skin.
• emollients and surfactants can of course be used in other applications.
• lipopolyamino acids can be used in detergent composites to which they confer a strong foaming, cleaning and thickening power.
• detergent composition means both composites intended for personal hygiene, in particular hair and p, as well as those more particularly intended for washing, cleaning or maintaining floors and surfaces, dishes and especially textiles such as delicate textiles, wool, silk, linen or cotton.
• N-acylated lipopolyamino acids by lauroyl or cocoyl radical, in the form of alkaline salts.
• the pH of such detergent compositions is advantageously between 6 and 7
• detergent compositions usually contain from 10 to 30% by weight of lipopolyamino acids according to the invention.
• lipopolyamino acids according to the invention in detergent compositions has been demonstrated by comparing the foaming power with that of lipopolyamino acids obtained from animal proteins.
• an aqueous solution comprising only 20% by weight of a sodium salt of a lipopolyaminoaci resulting from the total hydrolysis of a soy protein and acyls by lauroyl radical, makes it possible to obtain a foam of identical quality to that obtained with an aqueous solution comprising 36% by weight of a sodium of a lipopolyamino acid, resulting from a total hydrolysis of collagen and acyls by a lauroyl radical.
• the lipopolyamino acids of the invention in particular those in the form of cobalt, iron, manganese, copper or zinc salt can be used as a medicament, intended for humans, animals or plants, in particular as an anti-inflammatory and antimicrobial medicament p their antibacterial and antifungal properties.
• lipopolyamino acids as antimicrobials are those N-acylated by an octanoyl or undecylenoyl radical.
• the monobasic and dibasic aluminum salts of lipopolyamino acids according to the invention are also useful as an antiperspirant agent for combating hyperhydrosis.
• the lipopolyamino acids of the present invention can also constitute active materials in compositions intended for agriculture, in particular as an agent for stimulating the growth of plants and / or agent for protecting against parasites bacteria and fungi.
• lipopolyamino acids of the invention obtained from proteins obtained from oilseed meal, had notable anti-radical properties, in particular those N-acylated by an oleic radical.
• the solution is brought to 70 ° C for one hour, allowed to cool to 30 ° C and acidified to pH 1.5 using a hydrochloric acid solution.
• the lower aqueous phase is removed, and the supernatant phase is washed with water at 70 ° C, until the elimination of hydrochloric acid. 600 g of water are added and the mixture is neutralized to pH 7 with a mo of an aqueous sodium hydroxide solution.
• reaction mass which is then adjusted to pH 3.5 with 380 cm sodium hydroxide at 30% w / w. 20 g of bleaching black are then added, the mixture is left in contact for one hour with stirring, then the suspension is filtered.
• the solution obtained is then brought to pH 10.5 using 3 cm of sodium hydroxide at 30% w / w, then heated to 40-45 ° C under v
• the wetting power of lipopolyamino acids according to the invention was measured according to the AFN0R NFT 73406 test on aqueous solutions containing 0.1 by weight of active material.
• the wetting power is inversely proportional to the time (in s) measured.
• the lipopolyamino acids tested are as follows:
• Tables II and III below relate to the nitrogen dosages, the measurements of lipopolyamino acid acids indices according to the invention obtained from oil cakes of various origin.
• compositions containing lipopolyamino acids according to the invention relate to compositions containing lipopolyamino acids according to the invention. They are all obtained by simple hot mixing (approximately 60 ° C.) of their various constituents The contents of these constituents are expressed in g.
• Composition for the physiological maintenance of the skin is Composition for the physiological maintenance of the skin.
• Lypopolyamino acids derived from soy proteins N-acylated by an oleic radical
• stearic acid 10 polyoxyethylene (100) stearate 5 cetyl alcohol 2 palmitoylpolyamino acids 10 glycerol 10

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• Health & Medical Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Organic Chemistry (AREA)
• General Health & Medical Sciences (AREA)
• Medicinal Chemistry (AREA)
• Veterinary Medicine (AREA)
• Pharmacology & Pharmacy (AREA)
• Animal Behavior & Ethology (AREA)
• Public Health (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Epidemiology (AREA)
• Proteomics, Peptides & Aminoacids (AREA)
• Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
• Biochemistry (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Botany (AREA)
• Bioinformatics & Cheminformatics (AREA)
• Wood Science & Technology (AREA)
• Pain & Pain Management (AREA)
• Oncology (AREA)
• Immunology (AREA)
• Communicable Diseases (AREA)
• Biophysics (AREA)
• Genetics & Genomics (AREA)
• Molecular Biology (AREA)
• Agronomy & Crop Science (AREA)
• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
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• Rheumatology (AREA)
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• Environmental Sciences (AREA)
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• Food Science & Technology (AREA)
• Polymers & Plastics (AREA)
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• Cosmetics (AREA)

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Cited By (10)

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Citations (4)

• 1991
  • 1991-05-22 FR FR9106143A patent/FR2676741A1/fr active Granted
• 1992
  • 1992-05-21 CA CA002109599A patent/CA2109599A1/fr not_active Abandoned
  • 1992-05-21 WO PCT/FR1992/000450 patent/WO1992020647A1/fr not_active Ceased
  • 1992-05-21 EP EP92911537A patent/EP0593506B1/fr not_active Revoked
  • 1992-05-21 JP JP4510470A patent/JPH07500312A/ja active Pending
  • 1992-05-21 DE DE69209505T patent/DE69209505T2/de not_active Revoked
  • 1992-05-21 AT AT92911537T patent/ATE136023T1/de not_active IP Right Cessation

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