WO2001000158A1 - Compositions cosmetiques contenant des composes d'ammonium quaternaire - Google Patents

Compositions cosmetiques contenant des composes d'ammonium quaternaire Download PDF

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WO2001000158A1
WO2001000158A1 PCT/US2000/017627 US0017627W WO0100158A1 WO 2001000158 A1 WO2001000158 A1 WO 2001000158A1 US 0017627 W US0017627 W US 0017627W WO 0100158 A1 WO0100158 A1 WO 0100158A1
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Prior art keywords
quaternary ammonium
skin
compositions
oil
present
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PCT/US2000/017627
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English (en)
Inventor
Erica Louise Evans
Kristina Emma Inge Vanoosthuyze
Marina Trani
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The Procter & Gamble Company
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Priority claimed from GBGB9915095.5A external-priority patent/GB9915095D0/en
Priority claimed from GBGB9915094.8A external-priority patent/GB9915094D0/en
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to AU57697/00A priority Critical patent/AU5769700A/en
Publication of WO2001000158A1 publication Critical patent/WO2001000158A1/fr

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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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/14—Quaternary ammonium compounds, e.g. edrophonium, choline
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/27—Zinc; Compounds thereof
    • 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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/29—Titanium; Compounds thereof
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42—Amides
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
    • 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
    • A61K8/67—Vitamins
    • A61K8/673—Vitamin B group
    • 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
    • A61K8/67—Vitamins
    • A61K8/673—Vitamin B group
    • A61K8/675—Vitamin B3 or vitamin B3 active, e.g. nicotinamide, nicotinic acid, nicotinyl aldehyde
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86—Polyethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • 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
    • 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
    • A61Q19/08—Anti-ageing preparations
    • 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
    • A61Q19/007—Preparations for dry skin

Definitions

  • the present invention relates to cosmetic compositions.
  • the present invention relates to cosmetic compositions that provide good delivery of the pharmaceutical active and are both pleasant and efficacious.
  • Quaternary ammonium agents are also known for use in cosmetic compositions. See, for example, WO-A-99/27904, WO-A-96/32089, and EP-A-789,076. Also, US-A-5, 804,205 which discloses skin care compositions which are claimed to provide a high degree of moisturisation without leaving a "tacky” or "sticky” residue.
  • the compositions contain quaternary ammonium compounds having two alkyl groups of 16-22 carbon atoms, humectant and non-irritating hydrophobic microspheres having an average particle size of less than 50 ⁇ m. It is claimed that the hydrophobic polymeric microspheres significantly reduce the "tackiness" associated with high humectant levels. However, some quaternary ammonium agents have a high melting temperature and so can be difficult to formulate with the above mentioned thermosensitive skin benefit agents.
  • compositions that are both pleasant to use and deliver the pharmaceutical active efficaciously are often affected by the need to apply an extra lotion or cream during their daily routine. It would improve user compliance if the pharmaceutical active could be delivered as part of the daily routine, via a composition that was both pleasant to use and efficacious.
  • compositions comprising at least one quaternary ammonium agent and at least one pharmaceutical agent provide good delivery of the pharmaceutical active and are both pleasant and efficacious.
  • the quaternary ammonium agents of the present invention can vesiculate the pharmaceutical agent and drive its deposition onto the skin. This results in a smooth and uniform application of the pharmaceutical agent to the skin with reduced negatives such as tack/stickiness/greasiness.
  • the quaternary ammonium agents help reduce the loss of pharmaceutical agent from the skin due to environmental factors such as water or abrasion.
  • the quaternary ammonium agents themselves deliver skin care benefits, such as good moisturisation, good skin feel, good skin softness.
  • a cosmetic composition comprising:
  • compositions of the present invention provide efficacious application of the pharmaceutical agent to the skin with low levels of the usual negatives such as tackiness, greasiness or loss to environmental factors.
  • compositions of the present invention comprise at least one quaternary ammonium agent and at least one pharmaceutical agent. These elements will be described in more detail below.
  • the present compositions can be used for any suitable purpose.
  • the present compositions are suitable for topical application to the skin.
  • the skin care compositions can be in the form of creams, lotions, gels, and the like.
  • the cosmetic compositions herein are in the form of an oil-in-water emulsion of one or more oil phases in an aqueous continuous phase, each oil phase comprising a single oily component or a mixture of oily components in miscible or homogeneous form but said different oil phases containing different materials or combinations of materials from each other.
  • compositions of the present invention preferably comprise vesicles.
  • said vesicles comprise quaternary ammonium compound together with pharmaceutical agent.
  • vesicle means one or more bilayers arranged in a closed, usually spherical geometry, said biiayer comprises quaternary ammonium agent as described hereinbelow.
  • compositions of the present invention comprise less than 10%, preferably less than 5%, more preferably less than 3%, even more preferably 0%, by weight, of anionic surfactant.
  • compositions of the present invention are preferably formulated so as to have a product viscosity of at least about 1 ,000 mPa.s and preferably in the range from about 1 ,000 to about 300,000 mPa.s, more preferably from about 2,500 to about 250,000 mPa.s and especially from about 5,000 to about 200,000 mPa.s (26.8°C, neat, Brookfield DV-II+ Spindle CP52/CP41).
  • compositions of the present invention must comprise at least one quaternary ammonium agent having a transition temperature of less than 50°C.
  • Any quaternary ammonium agent suitable for use in cosmetic compositions may be used herein.
  • the term "quaternary ammonium agent” means a compound or mixture of compounds having a quaternary nitrogen atom substituted with one or more, preferably two, moieties containing six or more carbon atoms.
  • the quaternary ammonium agents for use herein are selected from those having a quaternary nitrogen substituted with two moieties wherein each moiety comprises ten or more, preferably 12 or more, carbon atoms.
  • Highly preferred quaternary ammonium agents for use herein are selected from those which are able to form vesicles in polar solvents, as detected by microscopic analysis (polarised light microscopy at a magnification of x60 using a Nikon Eclipse E800 microscope).
  • the present compositions comprise at least 0.01 %, more preferably at least 0.1 %, even more preferably at least 1.5%, still more preferably at least 3%, by weight, of quaternary ammonium agent.
  • quaternary ammonium agents for use herein are selected from:
  • Ri & R 2 are each C 1 -C 4 alkyl or C 1 -C 4 hydroxyalkyl groups or hydrogen.
  • R 3 & R-t are each alkyl or alkenyl groups having from about 8 to about 22 carbon atoms.
  • X " is a salt forming anion, compatible with quaternary ammonium compounds and other adjunct ingredients.
  • Preferred quaternary ammonium compounds of this type are quaternised amines having the general formula (I) where R-i & R 2 are methyl or hydroxyethyl and R 3 & R 4 are linear or branched alkyl or alkenyl chains comprising at least 11 atoms, preferably at least 15 carbon atoms.
  • each R 5 unit is independently selected from hydrogen, branched or straight chain C C 6 alkyl, branched or straight chain C ⁇ -C 6 hydroxyalkyl and mixtures thereof, preferably methyl and hydroxyethyl; each R 6 unit is independently linear or branched Cn-C 22 alkyl, linear or branched Cn-C 22 alkenyl, and mixtures thereof;
  • X " is an anion which is compatible with skin care actives and adjunct ingredients;
  • m is from 1 to 4, preferably 2;
  • n is from 1 to 4, preferably 2 and Q is a carbonyl unit selected from:
  • R 7 is hydrogen, C- 1 -C4 alkyl, C C 4 hydroxyalkyl, and mixtures thereof.
  • the unit -QR 6 contains a fatty acyl unit which is typically derived from a triglyceride source.
  • the triglyceride source is preferably derived from tallow, partially hydrogenated tallow, lard, partially hydrogenated lard, vegetable oils and/or partially hydrogenated vegetable oils, such as, canola oil, safflower oil, peanut oil, rapeseed oil, sunflower oil, corn oil, soybean oil, tall oil, rice bran oil, etc. and mixtures of these oils.
  • the counterion, X " in the above compounds can be any compatible anion, preferably the anion of a strong acid, for example, chloride, bromide, methylsulfate, ethylsulfate, sulfate, nitrate and the like, more preferably chloride or methyl sulfate.
  • the anion can also, but less preferably, carry a double charge in which case X " represents half a group.
  • the preferred quaternary ammonium compounds of the present invention are the diester and/or diamide Quaternary Ammonium (DEQA) compounds, the diesters and diamides having general formula (II), wherein the carbonyl group Q is selected from:
  • Tallow, canola and palm oil are convenient and inexpensive sources of fatty acyl units which are suitable for use in the present invention as Re units.
  • the counterion, X " can be chloride, bromide, methylsulfate, formate, sulfate, nitrate, and mixtures thereof.
  • the anion, X is merely present as a counterion of the positively charged quaternary ammonium compounds. The scope of this invention is not considered limited to any particular anion.
  • Rg is an acyclic aliphatic Ci 5 -C 2 ⁇ hydrocarbon group and R- ⁇ 0 is a C C-6 alkyl or alkylene group.
  • ammonium compounds having a pKa value of not greater than about 4, are able to generate a cationic charge in situ when dispersed in an aqueous solution, providing that the pH of the final composition is not greater than about 6.
  • Rg & R 10 are as specified hereinabove and Rn is selected from C C 4 alkyl and hydroxyalkyl groups.
  • the counterion, X " can be chloride, bromide, methylsulfate, formate, sulfate, nitrate, and mixtures thereof.
  • the anion, X is merely present as a counterion of the positively charged quaternary ammonium compounds. The scope of this invention is not considered limited to any particular anion.
  • Rg is selected from acyclic aliphatic C15-C21 hydrocarbon groups and R- ⁇ 2 is selected from C C alkyl and hydroxyalkyl groups.
  • ammonium compounds (VIII) having a pKa value of not greater than about 4, are able to generate a cationic charge in situ when dispersed in an aqueous solution, providing that the pH of the final composition is not greater than about 6.
  • the counterion, X " (IX) can be chloride, bromide, methylsulfate, formate, sulfate, nitrate, and mixtures thereof.
  • the anion, X is merely present as a counterion of the positively charged quaternary ammonium compounds. The scope of this invention is not considered limited to any particular anion.
  • R 13 is selected from C- ⁇ -C- 6 alkylene groups, preferably an ethylene group and z is from 0 to 4.
  • the preferred quaternary ammonium agents for use in the present invention are those described in section (b) hereinabove.
  • diester and/or diamide quaternary ammonium (DEQA) compounds according to general formula (II) hereinabove are preferred.
  • Preferred diesters for use herein are those according to general formula (II) wherein R 5 , R 6 , and X " are as defined hereinabove and Q is:
  • Preferred diamides for use herein are those according to general formula (II) wherein R 5 , R 6 , and X " are as defined hereinabove and Q is:
  • Preferred examples of quaternary ammonium compounds suitable for use in the compositions of the present invention are N,N-di(canolyl-oxy-ethyl)-N,N-dimethyl ammonium chloride, N,N- di(canolyl-oxy-ethyl)-N-methyl,N-(2-hydroxyethyl) ammonium methyl sulfate, N,N-di(canolyl-oxy-ethyl)-N-methyl, N-(2- hydroxyethyl) ammonium chloride and mixtures thereof.
  • Particularly preferred for use herein is N,N-di(canolyl-oxy-ethyl)-N-methyl,N-(2-hydroxyethyl) ammonium methyl sulfate.
  • quaternary ammonium compounds are derived from “canolyl” fatty acyl groups are preferred, other suitable examples of quaternary ammonium compounds are derived from fatty acyl groups wherein the term “canolyl” in the above examples is replaced by the terms “tallowyl, cocoyl, palmyl, lauryl, oleyl, ricinoleyl, stearyl, palmityl” which correspond to the triglyceride source from which the fatty acyl units are derived.
  • These alternative fatty acyl sources can comprise either fully saturated, or preferably at least partly unsaturated chains.
  • a second essential element of the compositions of the present invention is that they comprise at least one pharmaceutical agent.
  • Any pharmaceutical agent may be used herein provided it is compatible for use in cosmetic compositions.
  • Highly preferred pharmaceutical agents are selected from corticosteroids and mixtures thereof (e.g. cortisone and derivatives, betamethasone and derivatives, hydrocortisone and derivatives, dexamethasone, prednisolone and derivatives, triamcinolone), antimycotics and mixtures thereof (e.g. econazole, ketoconazole, hexetinem metronidazole, tioconazole, clotrimazole, griseofulvine), antihistamines (e.g.
  • procaine benzocaine, amylocaine, lidocaine
  • non-steroidal anti-infammatory drugs e.g. ammoniumsalicylate, methylsalicylate, indomethacine, ibuprofen, diclofenac, flufenamic acid
  • anti- acne and anti-psoriasis allantoin, aloe extract, benzoyl peroxide, bisabolol, dehydroacetic acid, erythromycin, farnesol and derivatives, ichtyol, lactic acid, metronidazole, minocycline, niacinamide, resorcinol, salicylic acid, sulfur, tea tree oil, tetracycline, tocopherol, vitamin D 3 and derivatives, zinc oxide, zinc pyrithion), depilating agents (e.g.
  • Preferred pharmaceutical actives for use herein include corticosteroids, non- steroidal anti-infammatory drugs, anti-acne and anti-psoriasis actives, and mixtures thereof.
  • compositions of the present invention comprise at least 0.01 %, more preferably at least about 0.1 %, even more preferably at least about 0.5%, by weight, of pharmaceutical active.
  • compositions herein can contain a variety of optional components suitable for rendering the present compositions more cosmetically or aesthetically acceptable or to provide them with additional usage benefits.
  • optional ingredients are well-known to those skilled in the art. These include any cosmetically acceptable ingredients such as those found in the CTFA International Cosmetic Ingredient Dictionary and Handbook, 7th edition, edited by Wenninger and McEwen, (The Cosmetic, Toiletry, and Fragrance Association, Inc., Washington, D.C., 1997). Some non-limiting examples of these optional ingredients are given below.
  • compositions of the present invention comprise a skin benefit agent.
  • skin benefit agent means any compound or mixture of compounds which, for example, gives moisturisation, protection, skin feel, skin softness and/or skin smoothness benefits to the skin.
  • Preferred skin benefit agents for use herein are humectants, emollients and mixtures thereof.
  • the compositions of the present invention comprise humectants and emollients.
  • compositions of the present invention comprise at least 1 % by weight of skin benefit agent. More preferably the present compositions comprise from 2% to 70%, preferably 5% to 60%, even more preferably 10% to 55%, by weight of skin benefit agent.
  • Humectant A highly preferred optional ingredient for the compositions of the present invention is humectant.
  • the term "humectant” means a substance which provides the skin with water-retention benefits.
  • the compositions of the present invention comprise at least 1 %, more preferably at least 5%, even more preferably at least 10%, even more still preferably at least 20%, by weight of humectant.
  • any humectant suitable for use in cosmetic compositions may be used herein.
  • suitable humectants for use in the present invention are described in WO98/22085, WO98/18444 and WO97/01326.
  • the humectants for use herein are selected from, but not limited to; amino acids and derivatives thereof such as proiine and arginine aspartate, 1 ,3-butylene glycol, and water and codium tomentosum extract, collagen amino acids or peptides, creatinine, diglyceroi, biosaccharide gum-1 , glucamine salts, glucuronic acid salts, glutamic acid salts, polyethylene glycol ethers of glycerine (e.g.
  • glycereth 20 glycerine, glycerol monopropoxylate, glycogen, hexylene glycol, honey, and extracts or derivatives thereof, hydrogenated starch hydrolysates, hydrolyzed mucopolysaccharides, inositol, keratin amino acids, urea, LAREX A-200 (available from Larex), glycosaminoglycans, methoxy PEG 10, methyl gluceth-10 and -20 (both commercially available from Amerchol located in Edison, NJ), methyl glucose, 3-methyl-1 ,3-butanediol, N-acetyl glucosamine salts, polyethylene glycol and derivatives thereof (such as PEG 15 butanediol, PEG 4, PEG 5 pentaerythitol, PEG 6, PEG 8, PEG 9), pentaerythitol, 1 ,2 pentanediol, PPG-1 glyceryl ether, PPG-9, 2-
  • the humectants for use herein are selected from glycerine, butylene glycol, and derivatives thereof, or mixtures thereof. Even more preferably, the humectant for use herein is glycerine.
  • Emollients are selected from glycerine, butylene glycol, and derivatives thereof, or mixtures thereof. Even more preferably, the humectant for use herein is glycerine.
  • compositions of the present invention are emollient.
  • Emollients tend to lubricate the skin, increase the smoothness and suppleness of the skin, prevent or relieve dryness of the skin, and/or protect the skin.
  • suitable emollients are known and may be used herein. Sagarin, Cosmetics, Science and Technology, 2nd Edition, Vol. 1, pp. 32-43 (1972) contains numerous examples of materials suitable for use as emollients.
  • the compositions of the present invention comprise greater than 1 %, more preferably at least 5%, even more preferably at least 10%, by weight, of emollient.
  • the emollients for use herein are selected from: i) Straight and branched chain hydrocarbons having from about 7 to about 40 carbon atoms, such as dodecane, squalane, petrolatum, cholesterol and derivatives thereof, hydrogenated polyisobutylene, isohexadecane and the C -C 4 o isoparaffins, which are C -C 4 o branched hydrocarbons. ii) C1-C 30 alcohol esters of C1-C 3 0 carboxylic acids and of C-2-C 30 dicarboxylic acids, e.g.
  • isononyl isononanoate isopropyl myristate, myristyl propionate, isopropyl stearate, behenyl behenate, dioctyl maleate, diisopropyl adipate, and diisopropyl dilinoleate.
  • Suitable polyethylene glycol derivatives of glycerides include PEG-20 almond glycerides, PEG-60 almond glycerides, PEG-11 avocado glycerides, PEG-6 capric/caprylic glycerides, PEG-8 capric/caprylic glycerides, PEG-20 corn glycerides, PEG-60 corn glycerides, PEG-60 evening primose glycerides, PEG-7 glyceryl cocoate, PEG-30 glyceryl cocoate, PEG-40 glyceryl cocoate, PEG-78 glyceryl cocoate, PEG-80 glyceryl cocoate, PEG-12 glyceryl dioleate, PEG-15 glyceryl isostearate, PEG-20 glyceryl isostearate, PEG-30 glyceryl isostearate, PEG-75 cocoa butter glycerides, PEG-20 hydrogenated palm oil glycerides, PEG-70 mango glycerides
  • alkylene glycol esters of CrC 30 carboxylic acids e.g. ethylene glycol mono- and di- esters, and propyiene glycol mono- and di- esters of C1-C30 carboxylic acids e.g., ethylene glycol distearate.
  • Organopolysiloxane oils Organopolysiloxane oils.
  • the organopolysiloxane oil may be volatile, nonvolatile, or a mixture of volatile and non-volatile siiicones.
  • nonvolatile refers to those siiicones that are liquid under ambient conditions and have a flash point (under one atmospheric of pressure) of or greater than about 100°C.
  • volatile refers to all other silicone oils.
  • Suitable organopolysiloxanes can be selected from a wide variety of siiicones spanning a broad range of volatilities and viscosities. Non-volatile polysiloxanes are preferred. Suitable siiicones are disclosed in U.S. Patent No. 5,069,897, issued December 3, 1991.
  • organopolysiloxanes selected from polyalkylsiloxanes, alkyl substituted dimethicones, dimethiconols, polyalkylaryl siloxanes, and mixtures thereof. More preferred for use herein are polyalkylsiloxanes and cyclomethicones. Preferred among the polyalkylsiloxanes are dimethicones. vi) Vegetable oils and hydrogenated vegetable oils.
  • vegetable oils and hydrogenated vegetable oils include safflower oil, castor oil, coconut oil, cottonseed oil, menhaden oil, palm kernel oil, palm oil, peanut oil, soybean oil, rapeseed oil, linseed oil, rice bran oil, pine oil, sesame oil, sunflower seed oil, partially and fully hydrogenated oils from the foregoing sources, and mixtures thereof.
  • animal fats and oils e.g. cod liver oil, lanolin and derivatives thereof such as acetylated lanolin and isopropyl lanolate.
  • Lanolin oil is preferred.
  • C 4 -C 2 o alkyl ethers of polypropylene glycols C1-C20 carboxylic acid esters of polypropylene glycols, and di- C 8 -C 3 o alkyl ethers, examples of which include PPG-14 butyl ether, PPG-15 stearyl ether, dioctyl ether, dodecyl octyl ether, and mixtures thereof.
  • polyol carboxylic acid esters examples of which include PPG-14 butyl ether, PPG-15 stearyl ether, dioctyl ether, dodecyl octyl ether, and mixtures thereof.
  • polyol carboxylic acid esters examples of which include PPG-14 butyl ether, PPG-15 stearyl ether, dioctyl ether, dodecyl octyl ether, and mixtures thereof.
  • polyol carboxylic acid esters examples of which include PPG-14 but
  • Preferred emollients for use in the compositions herein are selected from dodecane, squalane, cholesterol and derivatives thereof, isohexadecane, isononyl isononanoate, petrolatum, lanolin and derivatives thereof, safflower oil, castor oil, coconut oil, cottonseed oil, palm kernel oil, palm oil, peanut oil, soybean oil, polyol carboxylic acid esters and mixtures thereof. More preferred emollients for use herein are selected from polyol carboxylic acid esters, petrolatum and mixtures thereof.
  • esters are derived from a sugar or polyol moiety and one or more carboxylic acid moieties. Depending on the constituent acid and sugar, these esters can be in either liquid or solid form at room temperature.
  • liquid esters include: glucose tetraoleate, the glucose tetraesters of soybean oil fatty acids (unsaturated), the mannose tetraesters of mixed soybean oil fatty acids, the galactose tetraesters of oleic acid, the arabinose tetraesters of linoleic acid, xylose tetralinoleate, galactose pentaoleate, sorbitol tetraoleate, the sorbitol hexaesters of unsaturated soybean oil fatty acids, xylitol pentaoleate, sucrose tetraoleate, sucrose pentaoletate, sucrose hexaoleate, sucrose hepatoleate, suc
  • solid esters include: sorbitol hexaester in which the carboxylic acid ester moieties are palmitoleate and arachidate in a 1 :2 molar ratio; the octaester of raffinose in which the carboxylic acid ester moieties are linoleate and behenate in a 1 :3 molar ratio; the heptaester of maltose wherein the esterifying carboxylic acid moieties are sunflower seed oil fatty acids and lignocerate in a 3:4 molar ratio; the octaester of sucrose wherein the esterifying carboxylic acid moieties are oleate and behenate in a 2:6 molar ratio; and the octaester of sucrose wherein the esterifying carboxylic acid moieties are laurate, linoleate and behenate in a 1 :3:4 molar ratio.
  • a preferred solid material is sucrose polyester in which the degree of esterification is 7-8, and in which the fatty acid moieties are C18 mono- and/or di-unsatu rated and behenic, in a molar ratio of unsaturates: behenic of 1 :7 to 3:5.
  • a particularly preferred solid sugar polyester is the octaester of sucrose in which there are about 7 behenic fatty acid moieties and about 1 oleic acid moiety in the molecule.
  • Other materials include cottonseed oil or soybean oil fatty acid esters of sucrose. The ester materials are further described in, U. S. Patent No. 2,831 ,854, U. S. Patent No. 4,005,196, to Jandacek, issued January 25, 1977; U. S.
  • the polyol fatty acid polyesters suitable for use herein can be prepared by a variety of methods well known to those skilled in the art. These methods include: transesterification of the polyol with methyl, ethyl or glycerol fatty acid esters using a variety of catalysts; acylation of the polyol with a fatty acid chloride; acylation of the polyol with a fatty acid anhydride; and acylation of the polyol with a fatty acid, per se. See, for example, U.S. Patent No. 2,831 ,854; U.S. Patent No. 4,005,196, to Jandacek, issued January 25, 1977.
  • skin benefit agents may be useful in the compositions of the present invention.
  • examples of other skin benefit agents that may be used in the present compositions include:
  • the present compositions may comprise vitamin compounds, precursors, and derivatives thereof. These vitamin compounds may be in either natural or synthetic form. Suitable vitamin compounds include, Vitamin A (e.g., beta carotene, retinoic acid, retinol, retinoids, retinyl palmitate, retinyl proprionate, etc.), Vitamin B (e.g., niacin, niacinamide, riboflavin, pantothenic acid, etc.), Vitamin C (e.g., ascorbic acid, etc.), Vitamin D (e.g., ergosterol, ergocalciferol, cholecalciferol, etc.), Vitamin E (e.g., tocopherol acetate, etc.), and Vitamin K (e.g., phytonadione, menadione, phthiocol, etc.) compounds.
  • Vitamin A e.g., beta carotene, retinoic acid, retinol, reti
  • vitamin B 3 compounds are particularly useful for regulating skin condition as described WO-A-97/39733.
  • the compositions of the present invention preferably comprise from about 0.01 % to about 50%, more preferably from about 0.1 % to about 10%, even more preferably from about 0.5% to about 5%, by weight, of the vitamin B 3 compound.
  • vitamin B 3 compound means a compound having the formula:
  • R is -CONH 2 (i.e., niacinamide), -COOH (i.e., nicotinic acid) or -CH 2 OH (i.e., nicotinyl alcohol); derivatives thereof; and salts of any of the foregoing.
  • Exemplary derivatives of the foregoing vitamin B 3 compounds include nicotinic acid esters, including non-vasodilating esters of nicotinic acid, nicotinyl amino acids, nicotinyl alcohol esters of carboxylic acids, nicotinic acid N-oxide and niacinamide N-oxide.
  • vitamin B 3 compounds are well known in the art and are commercially available from a number of sources, e.g., the Sigma Chemical Company (St. Louis, MO); ICN Biomedicals, Inc. (Irvin, CA) and Aldrich Chemical Company (Milwaukee, Wl).
  • the vitamin compounds may be included as the substantially pure material, or as an extract obtained by suitable physical and/or chemical isolation from natural (e.g., plant) sources.
  • anti-wrinkle and anti-skin atrophy actives examples include, but are not limited to, lactic acid and derivatives thereof, retinoic acid and its derivatives (e.g., cis and trans); retinol; retinyl esters; niacinamide, salicylic acid and derivatives thereof; sulfur- containing D and L amino acids and their derivatives and salts, particularly the N-acetyl derivatives, a preferred example of which is N-acetyl-L-cysteine; thiols, e.g., ethane thiol; hydroxy acids, phytic acid, lipoic acid; lysophosphatidic acid, and skin peel agents (e.g., phenol and the like).
  • retinoic acid and its derivatives e.g., cis and trans
  • retinol retinyl esters
  • niacinamide e.g., salicylic acid and derivatives thereof
  • compositions herein may also comprise sunscreen actives.
  • sunscreen agents are useful herein. These sunscreen agents include both organic compounds and their salts as well as inorganic particulate materials. Without being limited by theory, it is believed that sunscreen agents provide protection from ultraviolet radiation by one or more of the following mechanisms including absorption, scattering, and reflection of the ultraviolet radiation. Nonlimiting examples of these sunscreen agents are described in U.S. Patent No. 5,087,445, to Haffey et al., issued February 11 , 1992; U.S. Patent No. 5,073,372, to Turner et al., issued December 17, 1991 ; U.S. Patent No. 5,073,371 , to Turner et al. issued December 17, 1991 ; U.S. Patent No.
  • sunscreen agents are those selected from the group consisting of 2-ethylhexyl p-methoxycinnamate, octyl salicylate, octocrylene, oxybenzone, 2-ethylhexyl N,N-dimethylaminobenzoate, p-aminobenzoic acid, 2-phenyl-benzimidazole-5-sulfonic acid, homomenthyl salicylate, DEA p-methoxycinnamate, 4,4'methoxy-t-butyldibenzoylmethane, 4- isopropyldibenzoylmethane, 3-(4-methylbenzylidene) camphor, 3-benzylidene camphor, 4-N,N-dimethylaminobenzoic acid ester with 2,4- dihydroxybenzophenone, 4-N,N-dimethylaminobenzoic acid ester with 2- hydroxy-4-(2-hydroxyethoxy)benzophenone
  • sunscreen agents selected from the group consisting of 2-ethylhexyl N,N-dimethyl-p- aminobenzoate, 2-ethylhexyl p-methoxycinnamate, octocrylene, octyl salicylate, homomenthyl salicylate, p-aminobenzoic acid, oxybenzone, 2- phenylbenzimidazole-5-sulfonic acid, DEA p-methoxycinnamate, 4,4'-methoxy-t- butyldibenzoylmethane, 4-isopropyl dibenzoylmethane, 3-(4-methylbenzylidene) camphor, 3-benzylidene camphor, 4-N,N-(2-ethylhexyl)methylaminobenzoic acid ester with 4-(2-hydroxyeth-oxy)dibenzoylmethane, titanium dioxide, zinc oxide, iron oxide
  • SPF Sun Protection Factor
  • compositions of the present invention may also comprise polar solvent.
  • polar solvent Any polar solvent suitable for use in cosmetic compositions may be used herein.
  • the polar solvent must be sufficiently polar to drive the formation of vesicles in the present invention.
  • the polar solvent used in the compositions of the present invention is water.
  • compositions will comprise from 10% to 90%, more preferably from 20% to 80%, even more preferably from 30% to 60%, by weight, of polar solvent.
  • Other Optional Ingredients are preferably from 10% to 90%, more preferably from 20% to 80%, even more preferably from 30% to 60%, by weight, of polar solvent.
  • compositions of the present invention can comprise a wide range of other optional components. These additional components should be pharmaceutically acceptable.
  • additional components should be pharmaceutically acceptable.
  • functional classes of ingredients suitable for use in the compositions of the present invention include: abrasives, absorbents, anti-acne actives, anticaking agents, anti-dandruff agents, anti- perspirant agents, antioxidants, anti-viral actives, artificial tanning actives and accelerators, biological additives, bleach, bleach activators, brighteners, builders, buffering agents, chelating agents, chemical additives, colorants, cosmetics, cleansers, cosmetic astringents, cosmetic biocides, denaturants, deodorants, desquamation actives, depilatories, drug astringents, dyes, dye transfer agents, enzymes, external analgesics, foam generators, flavours, film formers, fragrance components, insect repellents, mildewcides, non-steroidal anti-inflammatory active, opacifying agents, oxidative dyes
  • pigments include pigments.
  • Pigments suitable for use in the compositions of the present invention can be organic and/or inorganic.
  • materials having a low colour or lustre such as matte finishing agents, and also light scattering agents.
  • suitable pigments are iron oxides, acyglutamate iron oxides, titanium dioxide, ultramarine blue, D&C dyes, carmine, and mixtures thereof.
  • compositions of the present invention are prepared in such a way that the quaternary ammonium compound forms vesicles. It is preferred that said vesicles also comprise humectant. Preferably said vesicles also comprise emollient. Even more preferably said vesicles comprise at least one pharmaceutical agent. In order to ensure optimal performance characteristics it is preferred that the compositions of the present invention are prepared as follows:
  • all or part of the quaternary ammonium agent is mixed with humectant, water soluble pharmaceutical agents, water soluble skin care actives (where included), and, preferably, polar solvent at a temperature which is higher than the melting point of the quaternary ammonium agent;
  • the mixture is vigorously agitated
  • the oil phase containing the emollients, the relevant thickener in case the said thickener is oil soluble, oil soluble pharmaceutical agents and any remaining quaternary ammonium agent are mixed together at a temperature which is higher than the melting point of the quaternary ammonium agent.
  • the aqueous phase is prepared separately. The water, the relevant thickener in case the said thickener is water soluble, and any remaining water soluble ingredients are heated to the same temperature as the oil phase.
  • step (vi) On production of the emulsion the mixture formed in step (i) is added to the aforementioned emulsion with agitation.
  • the cosmetic compositions of the present invention may be used in a conventional manner for the treatment of skin.
  • An effective amount of the composition typically from about 0.1 grams to about 50 grams, preferably from about 1 gram to about 20 grams, is applied to wet or dry, preferably wet, skin.
  • Application of the composition typically includes working the composition into the skin, generally with the hands and fingers. The composition is then left on the skin or, preferably, the skin is rinsed.
  • the preferred method of treating the skin therefore, comprises the steps of:
  • a preferred aspect of the present invention involves the above method with an application of the composition on dry skin before an application on wet skin.
  • a preferred method comprises:
  • Another preferred method comprises:
  • compositions are particularly useful when incorporated as part of a regular routine. Therefore, another preferred method comprises:
  • composition comprising:
  • compositions can also be useful in mitigating damage caused by exposure of the skin to ultra violet radiation, damage caused by exposure of the skin to water during swimming or similar water based exercise, damage caused by shaving or exfoliation or damage caused by exposure of the skin to water during bathing.
  • Example 11 the quaternary ammonium compound used is N,N-di(canolyl- oxy-ethyl)-N methyl, N-(2-hydroxyethyl)Ammonium Methyl Sulfate supplied by Goldschmidt, trade name Rewoquat WE18
  • Example 12 the quaternary ammonium compound used is N,N-di(canolyl- oxy-ethyl)-N methyl, N-(2-hydroxyethyl)Ammonium Chloride supplied by Goldschmidt, developmental material (WE25)
  • Example13 the quaternary ammonium compound used is
  • Example 14 the quaternary ammonium compound used is
  • Example 25 the quaternary ammonium compound used is Methyl-1- tallowoylethyl-2-tallowimidazoline supplied by Goldschmidt, developmental material
  • Example 29 the quaternary ammonium compound used is Methyl-1- tallowamidoethyl-2-tallowimidazoline supplied by Goldschmidt, developmental material
  • Example 30 the quaternary ammonium compound used is Methyl-1- tallowoylethyl-2-tallowimidazolinium methyl sulfate supplied by Goldschmidt,
  • Example 32 the quaternary ammonium compound used is Methyl-1- tallowamidoethyl-2-tallowimidazolinium methyl sulfate supplied by
  • Example 39 the quaternary ammonium compound used is N.N-Dimethyl-N-
  • Example 40 the quaternary ammonium compound used is N,N-Dimethyl-N-
  • Example 42 the quaternary ammonium compound used is N,N'-Bis(2- talloyloxyethyl)-N,N,N',N'-Tetramethylene Diammonium Dichloride, as disclosed in patents US 4728337, US 4721512, US 4906413 from Ciba-Geigy
  • Example 43 the quaternary ammonium compound used is N,N'-Bis(2- canolyloxyethyl)-N,N'-Dimethyl-N,N'-(2-Hydroxyethyl)-1 ,6-Hexane
  • Example 44 the quaternary ammonium compound used is the di and oligo ester quats made by the reaction of fatty acid, di functional (or multi functional) acid and triethanolamine followed by quatemisation as disclosed in
  • Premix 1 Combine components of group A together at a temperature greater than the transition temperature of the chosen quaternary ammonium compound, keeping back a predetermined part of the quaternary ammonium compound and water. Vigorously agitate this premix.
  • Premix 2 Combine components of groups B and C with the remaining parts of the quaternary ammonium compounds and water not previously used in premix 1. Heat above the melting point of the quat and the oils.
  • Premix 1 Combine components of group A together at a temperature greater than the transition temperature of the chosen quaternary ammonium compound, keeping back a predetermined part of the water. Vigorously agitate this premix.
  • Premix 2 Combine with agitation the components of group D with the water not previously used in premix 1.
  • compositions of the above examples provide good skin care benefits, such as good moisturisation, good hydration, good skin feel, good skin softness and/or good skin smoothness, with low levels of negatives such as greasiness, stickiness or tack.

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Abstract

L'invention concerne une composition cosmétique comprenant (a) au moins un ammonium quaternaire, et (b) au moins un agent pharmaceutique. Les compositions selon l'invention permettent d'appliquer efficacement l'agent pharmaceutique sur la peau, avec un minimum d'effets négatifs, c'est-à-dire sans que le produit ait tendance à coller ou à graisser, et sans réduction de l'efficacité due à des facteurs environnementaux.
PCT/US2000/017627 1999-06-28 2000-06-27 Compositions cosmetiques contenant des composes d'ammonium quaternaire WO2001000158A1 (fr)

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GB9915095.5 1999-06-28
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GBGB9915095.5A GB9915095D0 (en) 1999-06-28 1999-06-28 Cosmetic compositions
GBGB9915094.8A GB9915094D0 (en) 1999-06-28 1999-06-28 Cosmetic compositions
US20188400P 2000-05-04 2000-05-04
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WO2003005985A1 (fr) * 2001-07-13 2003-01-23 The Procter & Gamble Company Compositions moussantes comprenant des agents d'ammonium quaternaire
WO2007137114A2 (fr) 2006-05-17 2007-11-29 Pioneer Hi-Bred International, Inc. Minichromosomes de plantes artificielles
EP2000123A1 (fr) * 2007-06-08 2008-12-10 Evonik Goldschmidt GmbH Compositions cosmétiques stables et peu visqueuses comprenant des esters quaternaires et/ou des dialkyles quaternaires
WO2013019411A1 (fr) 2011-08-03 2013-02-07 E. I. Du Pont De Nemours And Company Procédés et compositions permettant une intégration ciblée dans une plante
WO2013112686A1 (fr) 2012-01-27 2013-08-01 Pioneer Hi-Bred International, Inc. Procédés et compositions de génération de locus à traits complexes
WO2016040030A1 (fr) 2014-09-12 2016-03-17 E. I. Du Pont De Nemours And Company Production de sites d'intégration spécifique de site, pour des loci de traits complexes dans le maïs et le soja, et procédés d'utilisation
WO2016149352A1 (fr) 2015-03-19 2016-09-22 Pioneer Hi-Bred International Inc Procédés et compositions permettant d'accélérer l'introgression de caractères
WO2017079026A1 (fr) 2015-11-06 2017-05-11 E. I. Du Pont De Nemours And Company Génération de locus à traits complexes dans le soja et procédés d'utilisation
WO2023076898A1 (fr) 2021-10-25 2023-05-04 The Broad Institute, Inc. Procédés et compositions pour l'édition d'un génome à l'aide d'une édition primaire et d'une recombinase

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003005985A1 (fr) * 2001-07-13 2003-01-23 The Procter & Gamble Company Compositions moussantes comprenant des agents d'ammonium quaternaire
WO2007137114A2 (fr) 2006-05-17 2007-11-29 Pioneer Hi-Bred International, Inc. Minichromosomes de plantes artificielles
EP2308986A1 (fr) 2006-05-17 2011-04-13 Pioneer Hi-Bred International Inc. Mini-chromosomes de plantes artificielles
EP2000123A1 (fr) * 2007-06-08 2008-12-10 Evonik Goldschmidt GmbH Compositions cosmétiques stables et peu visqueuses comprenant des esters quaternaires et/ou des dialkyles quaternaires
WO2013019411A1 (fr) 2011-08-03 2013-02-07 E. I. Du Pont De Nemours And Company Procédés et compositions permettant une intégration ciblée dans une plante
WO2013112686A1 (fr) 2012-01-27 2013-08-01 Pioneer Hi-Bred International, Inc. Procédés et compositions de génération de locus à traits complexes
WO2016040030A1 (fr) 2014-09-12 2016-03-17 E. I. Du Pont De Nemours And Company Production de sites d'intégration spécifique de site, pour des loci de traits complexes dans le maïs et le soja, et procédés d'utilisation
EP3628739A1 (fr) 2014-09-12 2020-04-01 E. I. du Pont de Nemours and Company Production de sites d'intégration spécifique de site pour des loci de traits complexes dans le maïs et le soja et procédés d'utilisation
WO2016149352A1 (fr) 2015-03-19 2016-09-22 Pioneer Hi-Bred International Inc Procédés et compositions permettant d'accélérer l'introgression de caractères
EP4118955A1 (fr) 2015-03-19 2023-01-18 Pioneer Hi-Bred International, Inc. Compositions d'introgression de trait accélérée
WO2017079026A1 (fr) 2015-11-06 2017-05-11 E. I. Du Pont De Nemours And Company Génération de locus à traits complexes dans le soja et procédés d'utilisation
WO2023076898A1 (fr) 2021-10-25 2023-05-04 The Broad Institute, Inc. Procédés et compositions pour l'édition d'un génome à l'aide d'une édition primaire et d'une recombinase

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