EP2766348A1 - Benzodioxepin-3-on-verbindungen als farbstoffe oder als fluoreszierende emitter - Google Patents
Benzodioxepin-3-on-verbindungen als farbstoffe oder als fluoreszierende emitterInfo
- Publication number
- EP2766348A1 EP2766348A1 EP12761706.6A EP12761706A EP2766348A1 EP 2766348 A1 EP2766348 A1 EP 2766348A1 EP 12761706 A EP12761706 A EP 12761706A EP 2766348 A1 EP2766348 A1 EP 2766348A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- compounds
- alkyl
- formula
- group
- cycloalkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C09B13/00—Oxyketone dyes
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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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
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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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4986—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with sulfur as the only hetero atom
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- 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
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
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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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
- A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
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- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
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- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/10—The polymethine chain containing an even number of >CH- groups
- C09B23/105—The polymethine chain containing an even number of >CH- groups two >CH- groups
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/42—Colour properties
- A61K2800/43—Pigments; Dyes
- A61K2800/432—Direct dyes
- A61K2800/4324—Direct dyes in preparations for permanently dyeing the hair
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/42—Colour properties
- A61K2800/43—Pigments; Dyes
- A61K2800/434—Luminescent, Fluorescent; Optical brighteners; Photosensitizers
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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
- A61Q19/10—Washing or bathing preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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Definitions
- Dispersion diffuse into the matrix into it and optionally form a covalent bond to the matrix. Dyeing the matrix can thus be done in
- the present invention addresses the problem of providing alternative dyes having improved properties for dyeing a wide variety of substrates or making alternative compounds capable of protecting the skin and hair from photo-aging by visible light.
- OECs light-emitting electrochemical cells
- R aryl or heteroaryl group having 5 to 24 ring atoms or
- R 6 each independently of one another are H, D, OH, alkyl, aryl, cycloalkyl, O-alkyl, O-aryl or O-cycloalkyl,
- o 0 or 1
- allyl 2- or 3-butenyl, isobutenyl, sec-butenyl, 4-pentenyl, iso-pentenyl, hexenyl or decenyl.
- R 1 , R 2 , R 3 and R 4 are each
- the aryl group having 6 to 24 ring atoms for the substituents X and / or Y in the context of this invention is an aromatic group having a common aromatic electron system having 6 to 24 carbon atoms, optionally monosubstituted or polysubstituted by R.
- the aryl group having 6 to 24 carbon atoms is preferably R 1-substituted or unsubstituted 1, 2, 3, 4, 5 or 6-phenyl, 1, 2, 3, 4, 6, 7- or 8- Naphthyl, 1-, 2-, 3-, 4-, 6-, 7- or 8-phenanthrenyl, 1-, 2-, 3-, 4-, 5-, 6-, 7-,
- Diphenylmethane, biphenylene, triphenylene which may optionally be monosubstituted or polysubstituted by R, as described above or below.
- the aryl and / or heteroaryl groups are linked by a single bond.
- n is an integer from 0 to 5, in particular 0, 1, 2, 3 or 4, particularly preferably 0 or 1.
- R independently of each occurrence R is alkyl, OH, O-alkyl, O-aryl, S-alkyl, NH 2 , NHalkyl, N (alkyl) 2 , N (aryl) 2 , cycloalkyl, O-cycloalkyl , S-cycloalkyl, NH-cycloalkyl, N (cycloalkyl) 2 , CN, NO 2 , Si (alkyl) 3 , B (OR 6 ) 2 , C (O) R 6 , P (O) (R 6 ) 2 , S (O) R 6 , S (O) 2 R 6 , a straight-chain or branched alkenyl group having 2 to 20 C atoms and one or more double bonds or a straight-chain or branched alkynyl group having 2 to 20 C atoms and at least one triple bond and optionally one or more
- Each R independently is preferably Hal, alkyl, O-alkyl, O-aryl, NHalkyl, N (alkyl) 2 .
- Compounds of the formula I in which X and / or Y are substituted by this preferred group of R are
- R 5 is H, Hal or alkyl, very particularly preferably H.
- Alkyl in the definition of R 5 is preferably a straight-chain or branched alkyl group having 1 to 8 C atoms, which may optionally also be partially fluorinated.
- X and Y are each independently
- Cycloalkyl is a cyclic saturated or partially unsaturated
- R 1 , R 2 , R 3 and R 4 have the abovementioned or preferred meaning, with a compound of the formula IIIa and / or IIIb
- Alkali metal hydroxides such as sodium hydroxide or potassium hydroxide or strong organic bases such as lithium diisopropylamide.
- Alkali metal hydroxides used.
- the at least one aldehyde of the formula IIIa or IIIb is generally used in excess but at least one equivalent with respect to the compound of the formula II. If unsymmetrical compounds of the formula I are to be prepared, a mixture of 2 aldehydes of the formula IIIa and / or IIIb is added.
- the conversion into salts of the compounds of the formula I is achieved, for example, by adding an alkali or alkaline earth metal hydroxide, carbonate or bicarbonate in a polar solvent,
- These polymers may contain additional repeat units. These further repeat units are preferably selected from the group consisting of fluorenes (for example according to EP 842208 or US Pat
- the polymers may also have a plurality of different repeat units which are selected from one or more of the above-mentioned groups.
- Dyeing modified natural fibers such as regenerated cellulose, nitro, alkyl or hydroxyalkyl or acetyl cellulose.
- the keratin-containing fiber is human hair.
- the corresponding means for dyeing the keratin-containing fibers as described above contain the compound (s) of the formula I.
- developer components and coupler components are generally used in approximately molar amounts to each other.
- a certain excess of individual oxidation dye precursors is not disadvantageous, so that developer components and coupler components in a molar ratio of 1: 0.5 to 1: 3, in particular 1: 1 to 1: 2 , can stand.
- Suitable developer-type oxidation dye components are p-phenylenediamine and its derivatives.
- Coupler components such as e.g. o-diaminobenzenes or their derivatives are preferably selected from at least one compound from the group formed from 3,4-diaminobenzoic acid and 2,3-diamino-1-methylbenzene and their physiologically acceptable salts.
- Suitable coupler components are selected from 3-aminophenol, 5-amino-2-methylphenol, 3-amino-2-chloro-6-methylphenol, 2-hydroxy-4-aminophenoxyethanol, 5-amino-4-chloro-2-methylphenol, 5 - (2-
- the coupler components are preferably used in an amount of 0.0001 to 10 wt .-%, preferably 0.001 to 5 wt .-%, each based on the total agent.
- Direct dyes can be subdivided into anionic, cationic and nonionic substantive dyes.
- Basic Blue 26, Basic Violet 2 and Basic Violet 14 aromatic systems substituted with a quaternary nitrogen group, such as Basic Yellow 57, Basic Red 76, Basic Blue 99, Basic Brown 16 and Basic Brown 17, as well as
- direct dyes also naturally occurring dyes may be used, as for example in henna red, henna neutral, henna black, chamomile, sandalwood, black tea, buckthorn bark, sage, bluewood, madder root, Catechu, Sedre and alkano root are included.
- Oxidation staining are comparable.
- Carbonyl group contains (component (Oxo1))
- Component (Oxo1) is derived in this case c) from an aldehyde) to the carbon atom of the carbonyl group of the reactive carbonyl compound.
- Benzaldehyde and / or cinnamaldehyde and / or naphthaldehyde and / or at least one derivative of these abovementioned aldehydes, which in particular carry one or more hydroxyl, alkoxy or amino substituents, are very particularly preferably used as the reactive carbonyl component in the oxo dyeing.
- CH-acidic compounds are generally considered those compounds which carry a bound to an aliphatic carbon atom hydrogen atom, wherein due to electron-withdrawing substituents, activation of the corresponding carbon-hydrogen bond is effected.
- CH-acid compounds there are no limits to the choice of CH-acid compounds, as long as the
- a visible to the human eye colored compound is obtained.
- these are preferably those CH-acidic compounds which contain an aromatic and / or a heterocyclic radical.
- the heterocyclic radical may again be alphatic or aromatic.
- Particularly preferred are the CH-acidic
- the CH-acidic compounds of the oxo dye precursors of the component (oxo2a) are most preferably selected from at least one compound of the group consisting of 2- (2-furoyl) -acetonitrile, 2- (5-bromo-2-furoyl) -acetonitrile, 2- (5-methyl-2-trifluoromethyl-3-furoyl) -acetonitrile, 3- (2,5-dimethyl-3-furyl) -3-oxopropanitrile, 2- (2-thenoyl) -acetonitrile, 2- (3-thenoyl) -acetonitrile, 2- (5-fluoro-2-thenoyl) - acetonitrile, 2- (5-chloro-2-thenoyl) -acetonitrile, 2- (5-bro-2-thenoyl) -acetonitrile, 2- (2,5-dimethylpyrrol-3-oyl) -acetonitrile, 1H
- Oxidation dye precursor having at least one primary or secondary amino group and / or at least one hydroxy group can be used. Preferred suitable representatives are found under the execution of the oxidation dye precursors. However, it is
- the above-mentioned compounds of component (Oxo1) and the component (Oxo2) are, when used, each preferably in an amount of 0.03 to 65 mmol, in particular from 1 to 40 mmol, based on 100 g of the total Means, used.
- Hydrogen peroxide itself used.
- the hydrogen peroxide is added as a solution or in the form of a solid addition compound of hydrogen peroxide to inorganic or organic compounds, such as
- aqueous hydrogen peroxide solutions Very particular preference is given to aqueous hydrogen peroxide solutions.
- concentration of a hydrogen peroxide solution is determined on the one hand by the legal requirements and on the other hand by the desired effect; preferably 6-12% solutions in water are used.
- At least one bleach booster is preferably used in cosmetic compositions.
- Bleach boosters are preferably used to increase the bleaching action of the oxidizing agent, in particular the hydrogen peroxide.
- the peroxydisulfates in particular ammonium peroxydisulfate, are preferred.
- agents for dyeing and, if appropriate, simultaneous lightening of keratinic fibers are preferred, which additionally contain 0.01 to 2% by weight.
- Alkyl chain lengths such as those obtained with products based on natural fats and oils. Even with alkoxylated products, mixtures of different degrees of alkoxylation are usually present.
- purity in this context refers rather to the fact that the selected substances should preferably be free from solvents, stabilizers and other impurities.
- Ammonium compound from the group ammonium chloride
- Ammonium carbonate, ammonium bicarbonate, ammonium sulfate and / or ammonium carbamate in an amount of 0.5 to 10, preferably 1 to 5 wt .-%, based on the total composition of the composition.
- the dyeing and / or brightening agents according to the invention may contain further active ingredients, auxiliaries and additives, such as
- nonionic polymers such as vinyl pyrrolidone / vinyl acrylate copolymers, polyvinyl pyrrolidone and vinyl pyrrolidone / vinyl acetate copolymers and polysiloxanes,
- cationic polymers such as quaternized cellulose ethers, polysiloxanes with quaternary groups, dimethyldiallylammonium chloride polymers, acrylamide-dimethyldiallylammonium chloride copolymers, diethyl sulfate quaternized dimethylaminoethylmethacrylate-vinylpyrrolidone copolymers, vinylpyrrolidone-imidazolinium methochloride copolymers and quaternized polyvinyl alcohol,
- Thickeners such as agar-agar, guar gum, alginates, xanthan gum, gum arabic, karaya gum, locust bean gum, Linseed gums, dextrans, cellulose derivatives, eg methylcellulose, hydroxyalkylcellulose and carboxymethylcellulose, starch fractions and derivatives such as amylose, amylopectin and dextrins, clays such as e.g. As bentonite or fully synthetic hydrocolloids such.
- polyvinyl alcohol polyvinyl alcohol
- Protein hydrolysates in particular elastin, collagen, keratin, milk protein, soy protein and wheat protein hydrolysates, whose
- ZnO, ZnSO 4 zinc and its derivatives
- selenium and its derivatives eg selenium methionine
- stilbenes and their derivatives eg stilbene oxide , trans-stilbene oxide.
- R can be selected from the group -C (O) CH 3 , -CO 2 R 3 , -C (O) NH 2 and -C (O) N (R 4 ) 2 , X is O or NH, '
- the formaldehyde scavenger is selected from the group alkali metal, alkaline earth metal or ammonium disulfite.
- Particularly preferred is a formulation containing in combination DHA Plus, a mixture of DHA, sodium disulfite and magnesium stearate.
- DHA Plus is a product mixture used to mask, eliminate or neutralize the formaldehyde sodium metabisulfite,
- the flavonoid optionally present in the preparation additionally acts as a stabilizer for the self-tanner or the
- Self-tanning substances and / or reduces or avoids or improves storage-dependent off-odors which can also be caused by added additives or auxiliaries.
- the preferred flavonoids have a non-positively charged FlavangrundMech. It is believed that by these flavonoids
- Metal ions such as Fe 2+ / Cu 2+ be complexed and so autooxidation processes in fragrances or compounds whose degradation to
- DHA Rapid is a product mixture containing dihydroxyacetone and
- skin-lightening active ingredients can be all active ingredients known to the person skilled in the art.
- compounds with skin-lightening activity are hydroquinone, kojic acid, arbutin, aloesin or rucinol.
- the preparations may also contain anti-aging agents and thereby the predominantly visual anti-aging effect (protection against
- Vitamins and vitamin derivatives selected from vitamin A, vitamin A propionate, vitamin A palmitate, vitamin A acetate, retinol, vitamin B, thiamin chloride hydrochloride (vitamin Bi), riboflavin (vitamin B 2 ), nicotinamide, Vitamin C (ascorbic acid), vitamin D, ergocalciferol (vitamin D 2 ), vitamin E, DL-a-tocopherol, tocopherol-E-acetate, tocopherol hydrogen succinate, vitamin Ki, esculin (vitamin P active ingredient), thiamine (vitamin B-1 ), Nicotinic acid (niacin), pyridoxine, pyridoxal, pyridoxamine, (vitamin B 6 ), pantothenic acid, biotin, folic acid and cobalamin (vitamin Bi 2 ), particularly preferably vitamin A palmitate, vitamin C and its derivatives, a-tocopherol, tocopherol-E-acetate,
- Suitable preparations for external use for example as a cream or milk (O / W, W / O, O / W / O, W / O / W), as a lotion or emulsion, in the form of oily-alcoholic, oily-aqueous or aqueous alcoholic gels or solutions can be sprayed onto the skin. They can be present as solid pens or be packaged as aerosol.
- administration formulas such as capsules, dragees, powders, tablet solutions or solutions are suitable.
- an application form of the preparations to be used are, for example
- Surfactant-containing cleaning products may include the usual excipients such as salts of fatty alcohol sulfates, fatty alcohol ether sulfates, sulfosuccinic monoesters, fatty acid protein hydrolysates, isothionates, imidazolinium derivatives, methyl taurates, sarcosinates, fatty acid amide ether sulfates, alkyl amidobetaines, fatty alcohols, fatty acid glycerides, fatty acid diethanolamides, vegetable and synthetic oils, lanolin derivatives, ethoxylated glycerol - Contain fatty acid esters or mixtures of these substances.
- excipients such as salts of fatty alcohol sulfates, fatty alcohol ether sulfates, sulfosuccinic monoesters, fatty acid protein hydrolysates, isothionates, imidazolinium derivatives, methyl taurates, sarcosinate
- Oils such as triglycerides of capric or caprylic, further natural oils such. Castor oil;
- Fats, waxes and other natural and synthetic fats preferably esters of fatty acids with lower C-number alcohols, e.g. with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids of low C number or with fatty acids;
- the oil phase of the emulsions, oleogels or hydrodispersions or lipodispersions in the context of the present invention is advantageously selected from the group of esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids having a chain length of 3 to 30 carbon atoms and saturated and / or or unsaturated,
- the aqueous phase of the preparations to be used contains
- alcohols, diols or polyols of low C number, and their ethers preferably ethanol, isopropanol, propylene glycol, Glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and analogous products, furthermore lower C number alcohols, e.g. As ethanol, isopropanol, 1, 2-propanediol, glycerol, and in particular one or more thickeners, which or which can be advantageously selected from the group
- Silica aluminum silicates, polysaccharides or their derivatives, e.g. Hyaluronic acid, xanthan gum, hydroxypropylmethylcellulose, particularly advantageous from the group of polyacrylates, preferably a polyacrylate from the group of so-called Carbopols, for example Carbopols types 980, 981, 1382, 2984, 5984, each individually or in combination.
- Carbopols for example Carbopols types 980, 981, 1382, 2984, 5984, each individually or in combination.
- Emulsions are advantageous and contain z.
- the preparations to be used contain hydrophilic surfactants.
- the hydrophilic surfactants are preferably selected from the group of alkylglucosides, acyl lactylates, betaines and cocoamphoacetates.
- Emulsions, W / O emulsions and O / W emulsions are available in the usual way.
- emulsifiers for example, the known W / O and O / W emulsifiers can be used. It is advantageous to use other conventional co-emulsifiers in the preferred O / W emulsions.
- fatty alcohol ethoxylates from the group of the ethoxylated stearyl alcohols, cetyl alcohols, cetylstearyl alcohols (cetearyl alcohols).
- Polyethylene glycol (12) isostearate, polyethylene glycol (13) isostearate,
- Polyethylene glycol (14) isostearate, polyethylene glycol (15) isostearate,
- Polyethylene glycol (24) isostearate, polyethylene glycol (25) isostearate,
- Polyethylene glycol (20) oleate Polyethylene glycol (20) oleate.
- the sodium laureth-11-carboxylate can be advantageously used.
- the alkyl ether sulfate sodium laureth-4 sulfate can be advantageously used.
- polyethylene glycol (30) cholesteryl ether can be advantageously used.
- polyethylene glycol (25) soybean oil has been proven.
- polyethylene glycol glycerol fatty acid esters from the group consisting of polyethylene glycol (20) glyceryl laurate, polyethylene glycol (21) glyceryl laurate, polyethylene glycol (22) glyceryl laurate, polyethylene glycol (23) glyceryl laurate, polyethylene glycol (6) glyceryl caprate / citrate, polyethylene glycol (20) glyceryl oleate, polyethylene glycol (20) glyceryl isostearate, polyethylene glycol (18) glyceryl oleate (cocoate).
- polyethylene glycol (20) glyceryl laurate polyethylene glycol (21) glyceryl laurate
- polyethylene glycol (22) glyceryl laurate polyethylene glycol (23) glyceryl laurate
- polyethylene glycol (6) glyceryl caprate / citrate polyethylene glycol (20) glyceryl oleate
- Fatty alcohols having 8 to 30 carbon atoms monoglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids of a chain length of 8 to 24, in particular 12-18 C atoms, diglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids of one chain length from 8 to 24, in particular 12-18 C-atoms, monoglycerol ethers of saturated and / or unsaturated, branched and / or unbranched alcohols of one
- the preparation may contain cosmetic adjuvants which are commonly used in this type of preparations, e.g.
- surfactants such as soaps, emulsifiers, preservatives, antifoaming agents, perfumes, waxes, lanolin, propellants, dyes and / or pigments, and other ingredients commonly used in cosmetics.
- dispersion or solubilizing agent an oil, wax or other fatty substance, a low monoalcohol or a low polyol or mixtures thereof.
- Particularly preferred monoalcohols or polyols include ethanol, i-propanol, propylene glycol, glycerine and sorbitol.
- a preferred embodiment of the invention is an emulsion which is present as a protective cream or milk and contains, for example, fatty alcohols, fatty acids, fatty acid esters, in particular triglycerides of fatty acids, lanolin, natural and synthetic oils or waxes and emulsifiers in the presence of water.
- oily lotions based on natural or synthetic oils and waxes, lanolin,
- Fatty acid esters in particular triglycerides of fatty acids, or oily alcoholic lotions based on a lower alcohol, such as ethanol, or a glycerol, such as propylene glycol, and / or a polyol, such as glycerol, and oils, waxes and fatty acid esters, such as triglycerides of fatty acids.
- the preparation may also be in the form of an alcoholic gel comprising one or more lower alcohols or polyols, such as ethanol, propylene glycol or glycerin, and a thickener, such as silica.
- the oily alcoholic gels also contain natural or synthetic oil or wax.
- blowing agents are generally used, such as alkanes, fluoroalkanes and chlorofluoroalkanes, preferably alkanes.
- fluorescent emitters and therefore can also be used in an electronic device.
- Another object of the invention is therefore an electronic
- an electronic device is understood to mean a device which contains at least one layer which contains at least one organic compound.
- the component may also contain inorganic materials or layers, which
- the electronic device is preferably selected from the group consisting of organic electroluminescent devices (OLEDs), organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field quench devices (O-FQDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers) , “Organic plasmon emitting devices” (DM Koller et al., Nature Photonics 2008, 1-4) and electrophotography devices, preferably organic electroluminescent devices (OLEDs) or organic light-emitting electrochemical cells (OLECs).
- OLEDs organic electroluminescent devices
- O-ICs organic integrated circuits
- O-FETs organic field-effect transistors
- OF-TFTs organic thin-film transistors
- O-LETs organic light
- an optical outcoupling layer can be applied to one or both of the electrodes.
- An object of the invention is therefore furthermore a formulation or also composition comprising one or more compounds of the formula I as described above and at least one further organically functional material selected from the group of the host materials, matrix materials, electron transport materials,
- Electroluminescent device as described above, characterized
- the emitting layer is between 0.1 and 99.0 wt.%, Preferably between 0.5 and 50.0 wt.%, Particularly preferably between 1.0 and 20.0 wt.%, In particular between 1.0 and 10.0 wt.%. Accordingly, the proportion of the host material in the layer is between 1.0 and 99.9% by weight, preferably between 50.0 and 99.5% by weight, more preferably between 80.0 and 99.0% by weight, in particular between 90.0 and 99.0% by weight.
- ketones in particular ketones, phosphine oxides, sulfoxides, etc. (for example according to US Pat
- WO 05/084081 or WO 05/084082 the atropisomers (for example according to the unpublished application EP 04026402.0) or the boronic acid derivatives (eg according to the unpublished application EP 05009643.7).
- Particularly preferred host materials are selected from the classes of oligoarylenes containing naphthalene, anthracene and / or pyrene or atropisomers of these compounds, the oligo-arylenevinylenes, the ketones, the phosphine oxides and the sulfoxides. Very particularly preferred
- Host materials are selected from the classes of oligoarylenes containing anthracene and / or pyrene or atropisomers of these
- Particularly suitable matrix materials which can be used in combination with the compounds of the formula I according to the invention are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, eg. B. according to WO 2004/013080, WO 2004/093207, WO 2006/005627 or WO 2010/006680, triarylamines, carbazole derivatives, z. B.
- CBP ( ⁇ , ⁇ -biscarbazolylbiphenyl) or in WO 2005/039246, US 2005/0069729, JP 2004/288381, EP 1205527 or WO 2008/086851 disclosed carbazole derivatives, indolocarbazole derivatives, for. B. according to WO 2007/063754 or WO 2008/056746, Azacarbazolderivate, z. B. according to EP 1617710, EP 1617711, EP 1731584, JP 2005/347160, bipolar matrix materials, for. B. according to WO 2007/137725, silanes, z. B. according to WO 2005/111172, azaborole or boronic esters, z. B. according to
- WO 2006/117052 triazine derivatives, for. B. according to WO 2010/015306, WO 2007/063754 or WO 2008/056746, zinc complexes, for. B. according to
- Examples of the emitters described above can be found in the applications WO 00/70655, WO 2001/41512, WO 2002/02714, WO 2002/15645, EP 1 191613, EP 1191612, EP 1191614, WO 2005/033244, WO 2005/0 9373 and US Pat 2005/0258742 are taken.
- all phosphorescent complexes used in the prior art for phosphorescent OLEDs and as known to those skilled in the art of organic electroluminescence are suitable, and those skilled in the art may use other phosphorescent complexes without inventive step.
- Phosphorescent metal complexes preferably contain Ir, Ru, Pd, Pt, Os or Re.
- Preferred ligands for phosphorescent metal complexes are 2-phenylpyridine derivatives, 7,8-benzoquinoline derivatives, 2- (2-thienyl) -pyridine derivatives, 2- (1-naphthyl) pyridine derivatives or 2-phenylquinoline derivatives. All of these compounds may be substituted, e.g. for blue with fluorine, cyano and / or trifluoromethyl substituents.
- Auxiliary ligands are preferably acetylacetonate or picolinic acid.
- Phosphorescent complexes can be found in US 6835469 and US 6830828.
- the compounds of the formula I as described above can preferably be used in this application in combination with one or more further fluorescent materials (singlet emitters).
- fluorescent compounds (singlet emitters) are suitable
- Emit radiation for example. In the visible range and / or ultraviolet range and / or in the infrared range.
- Preferred dopants are selected from the class of the monostyrylamines, the distyrylamines, the tristyrylamines, the
- Tetrastyrylamines Tetrastyrylamines, styrylphosphines, styryl ethers and arylamines.
- the organic electroluminescent device according to the invention does not contain a separate hole injection layer and / or hole transport layer and / or hole blocking layer and / or electron transport layer, ie the emitting layer directly adjoins the hole injection layer or the anode, and / or the emitting layer directly adjoins the electron transport layer or the electron injection layer or the cathode, as described for example in WO 2005/053051.
- a metal complex which is the same or similar to the metal complex in the emitting layer, directly adjacent to the emitting layer as a hole transport. port or Lochinjetechnischsmaterial to use such.
- WO 2011/053051 it is possible to use a metal complex, which is the same or similar to the metal complex in the emitting layer, directly adjacent to the emitting layer as a hole transport. port or Lochinjetechnischsmaterial to use such.
- Formulations containing one or more of the compounds of the invention and one or more solvents are ideal for creating layers of solution.
- Suitable and preferred solvents are for example toluene, anisole, xylenes, methyl benzoate, dimethylanisole, trimethylbenzenes, tetralin, veratrole, tetrahydrofuran, chlorobenzene or dichlorobenzenes and
- the organic electroluminescent device according to the invention can be used for example in displays or for illumination purposes, but also for medical or cosmetic applications.
- the compounds according to the invention are suitable for use in light-emitting devices. Thus, these compounds are very versatile. Some of the main application areas are display or lighting technologies. Furthermore, it is particularly advantageous, the compounds and devices containing these
- Phototherapy or light therapy is used in many medical and / or cosmetic fields.
- the compounds according to the invention and the devices containing these compounds can therefore be used for the therapy and / or prophylaxis and / or diagnosis of all diseases and / or in cosmetic applications for which the person skilled in the art considers the use of phototherapy.
- the term phototherapy includes not only the radiation but also the photodynamic therapy (PDT) as well as disinfecting and sterilizing in general.
- Phototherapy or light therapy can treat not only humans or animals, but also any other type of living or inanimate matter. These include, for example, fungi, bacteria, microbes, viruses, eukaryotes, prokaryotes, foods, beverages, water and drinking water.
- phototherapy also includes any type of combination of light therapy and other types of therapy, such as the treatment with drugs.
- Many light therapies aim to have outer parts of one
- Object to irradiate or treat such as the skin of humans and animals, wounds, mucous membranes, eye, hair, nails, nail bed, gums and tongue.
- the treatment or irradiation according to the invention can also be carried out within an object in order to treat, for example, internal organs (heart, lungs, etc.) or blood vessels or the breast.
- the therapeutic and / or cosmetic fields of use according to the invention are preferably selected from the group of skin diseases and skin-associated diseases or changes or circumstances such as, for example, psoriasis, skin aging, skin fold formation,
- Skin rejuvenation enlarged skin pores, cellulite, oily / oily skin, folliculitis, actinic keratosis, precancerose actinic keratosis, skin lesions, sun-damaged and sun-stressed skin, crow's feet, skin ulcer, acne, acne rosacea, acne scars, acne bacteria, photomodulation greasy / oily Sebaceous glands and their surrounding tissues, jaundice, neonatal jaundice, vitiligo, skin cancer, skin tumors, Crigler Naijar, dermatitis, atopic dermatitis, diabetic skin ulcers and desensitization of the skin.
- Particularly preferred for the purposes of the invention are the treatment and / or prophylaxis of psoriasis, acne, cellulite, skin wrinkling, skin aging, jaundice and vitiligo.
- compositions and / or devices containing the compositions according to the invention are selected from the group of inflammatory diseases, rheumatoid arthritis, pain therapy, treatment of wounds, neurological diseases and conditions, edema, Paget's disease, primary and metastasizing tumors, connective tissue diseases or Changes, collagen, fibroblasts and fibroblast-derived cell levels in mammalian tissues, retinal irradiation, neovascular and hypertrophic diseases, allergic reactions, respiratory tract irradiation,
- Papillomavirus for the treatment of warts and genital warts.
- Further fields of application according to the invention for the compounds and / or devices comprising the compounds according to the invention are selected from winter depression, sleeping sickness, radiation to improve mood, alleviation of pain, especially muscle pain due to, for example, tension or joint pain, elimination of stiffness of joints and lightening of the teeth (bleaching).
- any type of object (inanimate matter) or subject matter may be treated for disinfection, sterilization or preservation purposes.
- object inanimate matter
- subject matter living matter such as human and animal
- disinfection, sterilization or preservation purposes include, for example, the disinfection of wounds, the reduction of bacteria, the disinfection of surgical instruments or other objects, the disinfection or preservation of food and food, of liquids, especially water, drinking water and other drinks, the disinfection of mucous membranes and Gums and teeth.
- Disinfection here means the reduction of living microbiological causative agents of undesired effects, such as bacteria and germs.
- devices containing the compounds according to the invention preferably emit light of the wavelength between 250 and 1250 nm, particularly preferably between 300 and 1000 nm and particularly preferably between 400 and 850 nm.
- the compounds of the invention in an organic light-emitting diode (OLED) or an organic light-emitting electrochemical cell (OLEC) are used for the purpose of phototherapy.
- Both the OLED and the OLEC can have a planar or fiber-like structure of any desired cross-section (for example, round, oval, polygonal, square) with a monolayer or multilayer structure.
- These OLECs and / or OLEDs may be incorporated into other devices including other mechanical, adhesive and / or electronic devices (e.g., battery and / or
- the use of said devices for said therapeutic and / or cosmetic purpose is particularly advantageous over the prior art, since with the aid of the devices according to the invention using the OLEDs and / or OLECs homogeneous irradiations of lower irradiation intensities at almost any location and at any time of day possible are.
- the irradiations may be performed inpatient, outpatient and / or self, i.e. without initiation by medical or cosmetic professionals.
- patches can be worn under clothing, so that irradiation is also possible during working hours, at leisure or during sleep.
- expensive inpatient / outpatient treatments can be omitted in many cases or reduce their frequency.
- the devices of the present invention may be for reuse or disposable items that may be disposed of after one, two, or three times use.
- the E1% value gives the extinction at the concentration of 1 g / 100 ml
- the compounds of the formula I for example the compounds of Examples 1, 3 and 8, cover a significantly larger spectral range. Although curcumin absorbs more intensely, it is not thermally stable.
- Beta carotene (comparison) 84 ° C
- the thermal stabilities are excellent, so too
- the substance concentrations in ethanol given in the table are measured with a fluorescence spectrometer of the brand Aminco Bowman 2 (layer thickness 1 cm, excitation 220-600 nm, emission 220-800 nm, spectral gap width (excitation) 4 nm, (emission) 8 nm;
- Example D-1 mild transparent W / O tanning lotion
- Example F-1 O-in-W emulsions for protection against visible radiation
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DE102011116165A DE102011116165A1 (de) | 2011-10-14 | 2011-10-14 | Benzodioxepin-3-on-Verbindungen |
PCT/EP2012/003869 WO2013053422A1 (de) | 2011-10-14 | 2012-09-17 | Benzodioxepin-3-on-verbindungen als farbstoffe oder als fluoreszierende emitter |
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- 2012-09-17 AU AU2012323521A patent/AU2012323521A1/en not_active Abandoned
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- 2012-09-17 IN IN1014KON2014 patent/IN2014KN01014A/en unknown
- 2012-09-17 WO PCT/EP2012/003869 patent/WO2013053422A1/de active Application Filing
- 2012-09-17 US US14/351,645 patent/US8907110B2/en not_active Expired - Fee Related
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See references of WO2013053422A1 * |
Also Published As
Publication number | Publication date |
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IN2014KN01014A (enrdf_load_stackoverflow) | 2015-10-09 |
KR20140090201A (ko) | 2014-07-16 |
JP2014534958A (ja) | 2014-12-25 |
US20140234238A1 (en) | 2014-08-21 |
DE102011116165A1 (de) | 2013-04-18 |
WO2013053422A1 (de) | 2013-04-18 |
US8907110B2 (en) | 2014-12-09 |
AU2012323521A1 (en) | 2014-05-29 |
CN103874687A (zh) | 2014-06-18 |
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