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WO2010053017A1 - Composition absorbant les ultraviolets, formulations cosmétiques et pharmaceutiques l’utilisant et procédé de blocage des ultraviolets - Google Patents

Composition absorbant les ultraviolets, formulations cosmétiques et pharmaceutiques l’utilisant et procédé de blocage des ultraviolets Download PDF

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Publication number
WO2010053017A1
WO2010053017A1 PCT/JP2009/068281 JP2009068281W WO2010053017A1 WO 2010053017 A1 WO2010053017 A1 WO 2010053017A1 JP 2009068281 W JP2009068281 W JP 2009068281W WO 2010053017 A1 WO2010053017 A1 WO 2010053017A1
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group
ultraviolet
absorbing composition
carbon atoms
compound
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PCT/JP2009/068281
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English (en)
Japanese (ja)
Inventor
ゆきえ 渡邊
桂三 木村
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富士フイルム株式会社
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Publication of WO2010053017A1 publication Critical patent/WO2010053017A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/08—Solutions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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

Definitions

  • the present invention relates to an ultraviolet absorbing composition, a cosmetic containing the same, a pharmaceutical preparation, and a method of blocking ultraviolet light using the ultraviolet absorbing composition.
  • UV-B radiation light having a wavelength in the range of 280 nm to 320 nm, known as UV-B radiation, more than the desired natural tanning condition of the skin Damage to the skin, causing harmful skin burns and causing erythema.
  • UV-B radiation For health and cosmetic reasons, to suppress harmful UV radiation damage, to prevent sunburn on skin and hair, or to control skin tone to a healthy sunburn condition while suppressing sunburn damage Means are needed. For this reason, it is desirable to shield this UV-B ray.
  • UV-A radiation which has a wavelength in the range of 320 nm to 400 nm and causes browning of the skin, may also cause dysfunction of the skin, so that sensitive skin and constant sun In the case of skin exposed to light rays, the effect is particularly concerned.
  • UV-A radiation in particular, causes the skin to lose its elasticity, causes wrinkles to appear and causes the skin to prematurely age.
  • UV-A radiation causes the development of erythema, and depending on the constitution, this reaction may be amplified to cause phototoxic or photoallergic reactions. Therefore, it is desirable to control the effects of UV-A radiation on the skin for such health reasons or for cosmetic reasons such as maintaining the elasticity of the skin, for example.
  • the field of application of the ultraviolet ray absorbing composition for human body includes skin care products such as sunscreen creams, shampoos, rinses, hair setting agents and the like, skin care products such as sportswear, stockings and hats, fibers for textiles, lenses of glasses, A contact lens, medical instruments, such as an artificial eye, etc. can be mentioned.
  • UV-absorptive materials include, for example, glass substitutes and their surface coatings, window glass for dwellings, facilities, transport equipment, etc., coating materials for daylighting glass and light source protective glass, dwellings, facilities, transport equipment Interior and exterior materials such as, interior and exterior coatings, members for light sources emitting ultraviolet light such as fluorescent lamps and mercury lamps, precision machinery, members for electronic and electrical equipment, materials for shielding electromagnetic waves generated from various displays, foods, chemicals, medicines, etc.
  • Optical goods, tapes, stationery such as ink, marking plates, marking devices, etc. and surface coating materials thereof can be mentioned.
  • UV absorber As an ultraviolet absorber applied to these various fields, what is excellent in safety, has high solubility, and a high molar absorptivity is desired.
  • conventional UV absorbers benzotriazole compounds, benzophenone compounds, salicylic acid compounds, triazine compounds, aminobenzoic acid compounds, cinnamic acid compounds, etc. are used, but these are safe and highly soluble. And the high molar extinction coefficient was not sufficiently satisfied.
  • methods for producing merocyanine compounds having excellent light absorbance in the ultraviolet light region have been proposed (see, for example, JP-A-53-128333 and JP-A-58-181041). However, the obtained compound is not sufficient in solubility, and therefore, a compound having excellent ultraviolet absorbing ability and further having excellent solubility has been desired.
  • the object of the present invention made in consideration of the above problems is to effectively block ultraviolet light in the UV-A region, and to be able to prepare with uniform physical properties even when various media are used,
  • An object of the present invention is to provide an ultraviolet absorbing composition having a high molar absorption coefficient and containing less coloring derived from the ultraviolet absorber.
  • a further object of the present invention is UV-absorbing cosmetics, pharmaceutical preparations having excellent safety for the human body and long-lasting effect using the UV-absorbing composition of the present invention, and further effective UV blocking. To provide a way.
  • the constitution of the present invention is as follows.
  • the concentration at 25 ° C becomes 1.0 ⁇ 10 -6 mol / L-1.0 ⁇ 10 -3 mol / L Solution containing 1.0.times.10.sup. - 7 mol / g to 1.0.times.10.sup.- 3 mol / g of a UV absorbing compound having a maximum absorption wavelength of 380 nm or less in a solution prepared as above, and a film having a thickness of 10 .mu.m
  • An ultraviolet ray absorbing composition having a light transmittance of 5% or less at a wavelength of 390 nm in the film.
  • the content of the ultraviolet ray absorbing compound is 1 ⁇ 10 ⁇ 4 g to 5 ⁇ 10 ⁇ 1 g in 1 g of the ultraviolet ray absorbing composition according to any one of [1] to [3].
  • UV absorbing composition [5] The ultraviolet absorbing composition according to any one of [1] to [4], wherein the molecular weight of the ultraviolet absorbing compound is in the range of 400 to 4,000.
  • R 11 , R 12 and R 13 each independently represent a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group bonded via a carbon atom
  • L 11 to L 14 each independently represent Represents a single bond or a divalent group
  • -X- represents -O-, -S-, -N- or -C (R 14 )-
  • R 14 represents a hydrogen atom or a substituent.
  • n 11 and n 12 are each independently an integer of 0 or more. However, when n 11 and n 12 are 1 or more at the same time, the order of arrangement of structural units forming a chain structure in [] is arbitrary.
  • n 13 represents 0 when -X- is -O- or -S-, and 1 when -X- is -N- or -C (R 14 )-.
  • Two or more substituents of R 11 , R 12 , R 13 , R 14 , L 11 , L 12 , L 13 and L 14 may combine with each other to form a ring.
  • R 31 and R 32 each independently represent a substituent having a ⁇ p value of 0.20 or more
  • R 33 , R 34 and R 35 each independently represent a hydrogen atom, an aliphatic group or an aromatic group. Or a heterocyclic group linked by a carbon atom.
  • R 11 to R 13 , L 11 to L 14 , -X-, n 11 , n 12 , R 33 , R 34 and R 35 each represents R 11 to R 11 in the general formula (Ia) It is synonymous with R 13 , L 11 to L 14 , -X-, n 11 , n 12 , R 33 , R 34 and R 35 respectively.
  • R36 and R37 each independently represent an aliphatic group, an aromatic group or a heterocyclic group bonded to one another via a carbon atom.
  • the ultraviolet absorbing composition according to any one of [1] to [8], which is an emulsion composition containing an oil phase component and an aqueous phase component.
  • a cosmetic comprising the ultraviolet absorbing composition according to any one of [1] to [10].
  • a pharmaceutical preparation comprising the ultraviolet absorbing composition according to any one of [1] to [10].
  • the present invention in addition to effectively blocking ultraviolet light in the UV-A region, it can be prepared with uniform physical properties even when various media are used, and the molar absorption coefficient is high and contained. It is possible to provide an ultraviolet absorbing composition with less coloration derived from an ultraviolet absorber. Further, according to the present invention, by using this ultraviolet light absorbing composition, cosmetics, pharmaceutical preparations, and further effective ultraviolet light having excellent ultraviolet light absorbing ability with excellent safety to the human body and long lasting effect. It is possible to provide a shutoff method.
  • UV ray absorbing composition The ultraviolet absorbing composition of the present invention is dissolved in a solvent having no maximum absorption in the wavelength range of 300 to 600 nm, and the concentration at 25 ° C.
  • a thin film with a thickness of 10 ⁇ m formed by this composition is a composition excellent in ultraviolet light absorbing ability that can effectively block light in the UV-A wavelength region of wavelength 390 nm.
  • the ultraviolet absorbing composition of the present invention is formed into a film and subjected to physical property evaluation.
  • the ultraviolet absorbing composition comprises an ultraviolet absorbing compound having absorption in a specific region, and a medium capable of dissolving, dispersing or emulsifying the same, which is formed into a film of 10 ⁇ m thickness for measurement.
  • a medium capable of dissolving, dispersing or emulsifying the same which is formed into a film of 10 ⁇ m thickness for measurement.
  • the medium used together with the ultraviolet absorbing compound organic solvents, water, resins and the like can be mentioned, but of course, it is not limited thereto.
  • the ultraviolet absorbing compound that can be used in the present invention has a maximum absorption wavelength in a solution of 1.0 ⁇ 10 ⁇ 6 mol / L to 1.0 ⁇ 10 ⁇ 3 mol / L prepared using a solvent as shown below It is a compound of 380 nm or less and has absorption in the UV-A region.
  • the maximum absorption wavelength is measured as follows.
  • Dissolve the UV absorber which is a sample, in a solvent of 1.0 ⁇ 10 -6 mol / L to 1.0 ⁇ 10 -3 mol / L in a solvent as shown below, and use a quartz or glass cell
  • a quartz or glass cell Preparing a cell for a sample containing the solution and a cell containing only a solvent, which does not contain an ultraviolet absorber which is a sample for control, and which is measured by a spectral absorption measurement apparatus using two cells,
  • the maximum absorption wavelength of the UV absorber as a sample is measured using the control cell as a standard.
  • the method is described in detail in, for example, “The 4th edition Experimental Chemistry Course 7 Spectroscopy II” edited by The Chemical Society of Japan, Maruzen, 1992, pp. 180-186, etc., and the measurement method is referred to. be able to.
  • the solvent to be used here may be selected in consideration of the good solubility of the ultraviolet light absorber, and further, it must have no maximum absorption in the same or a similar wavelength range as the ultraviolet light absorber to be measured, Since it is required that the interaction with the solute molecule is small and the volatility is not so remarkable, etc., it may be selected in consideration of these.
  • Any solvent can be selected as long as it satisfies the above conditions, but specifically, from the viewpoint of solubility, for example, amide solvents (eg, N, N-dimethylformamide, N, N -Dimethylacetamide, 1-methyl-2-pyrrolidone), sulfone solvents (eg, sulfolane), sulfoxide solvents (eg, dimethyl sulfoxide), ureido solvents (eg, tetramethylurea), alcohol solvents (eg, methanol) , Ethanol, isopropanol), ether solvents (eg, dioxane, cyclopentyl methyl ether), hydrocarbon solvents (eg, toluene, xylene, n-decane), halogen solvents (eg, tetrachloroethane, chlorobenzene), pyridine solvents (Eg, pyridine, ⁇ -picoline, 2, 6 Lut
  • ethyl acetate, toluene, tetrahydrofuran, dimethyl sulfoxide, acetone, acetonitrile, methyl ethyl ketone, dimethyl acetamide, dimethylformamide and the like are preferably mentioned.
  • the maximum absorption wavelength of the ultraviolet absorbing compound which can be used in the present invention is 25 at a solution having a concentration of 1.0 ⁇ 10 ⁇ 6 mol / L to 1.0 ⁇ 10 ⁇ 3 mol / L prepared using the solvent. Measured in ° C. Within the above concentration range, it is preferable to prepare a solution by controlling the concentration such that the absorbance is in the range of 0.1 to 2, preferably 1 to 2. The value measured using such a solution using a quartz cell with an optical path length of 10 mm is used.
  • the measuring apparatus is not particularly limited as long as it is a spectral absorption measuring apparatus, but in the present invention, measurement was performed using a U-4100 spectrophotometer manufactured by Hitachi High-Technologies Corporation.
  • the preferable content of the ultraviolet absorbing compound having a maximum absorption wavelength of 380 nm or less measured under the above conditions in the ultraviolet absorbing composition of the present invention is 5.0 ⁇ 10 ⁇ 7 to 0.5 ⁇ 10 It is preferably -3 mol / g, more preferably 1.0 ⁇ 10 -6 to 3.0 ⁇ 10 -4 mol / g, still more preferably 0.5 ⁇ 10 -6 to 1.0 ⁇ 10 -4. It is mol / g.
  • the ultraviolet absorbing composition of the present invention contains the ultraviolet absorbing compound at the above-mentioned content, and its physical property is defined by the light transmittance when this is formed into a film having a thickness of 10 ⁇ m.
  • the ultraviolet-ray absorption composition of this invention According to the use * kind, various forms, such as solid, powder, a liquid, a gel-like substance, a dispersion, an emulsion, can be taken.
  • a method of forming a membrane according to the dosage form will be described.
  • the ultraviolet absorbing composition When the ultraviolet absorbing composition is solid, it is stretched or sliced to prepare a 10 ⁇ m thick film, and the absorption spectrum is measured.
  • the ultraviolet absorbing composition When the ultraviolet absorbing composition is a powder, a disc is produced by compression molding, and the absorption spectrum is measured. If it is a liquid, it can be placed in a 10 ⁇ m thin layer cell to measure the absorption spectrum.
  • it when it is a gel-like material, it forms into a film so that it may become 10 micrometers in thickness on a transparent substrate, thickness can be confirmed with a film thickness measuring device, and an absorption spectrum can be measured.
  • the ultraviolet absorbing composition When the ultraviolet absorbing composition is in the form of a dispersion or an emulsion, it may be measured in the same manner as the liquid with a low viscosity, more specifically, a viscosity which can be poured into a thin layer cell.
  • a viscosity which can be poured into a thin layer cell.
  • Those having high viscosity for example, those having such a viscosity that a thin film of 10 ⁇ m can be formed on a transparent substrate, can be measured in the same manner as the gel-like material.
  • the film forming method of the film having a thickness of 10 ⁇ m is not limited to the above, and can be appropriately selected according to the form as long as a uniform film can be formed.
  • the measurement temperature is not particularly limited, but preferably 0 to 80 ° C.
  • the measuring apparatus can use a normal spectral absorption measuring apparatus.
  • a spectral absorption measuring apparatus (U-4100 spectrophotometer manufactured by Hitachi High-Technologies Corp.) is used as a measuring instrument. The value measured at 25 ° C. is used.
  • the ultraviolet absorbing composition of the present invention contained in the specific amount described above is a film having a thickness of 10 ⁇ m by the above method, the light transmittance of the wavelength of 390 nm in the formed film needs to be 5% or less. This means that even a thin film can efficiently absorb and block short wavelength ultraviolet light.
  • the light transmittance of a wavelength of 440 nm in the film having a thickness of 10 ⁇ m formed in this way is 80% or more, and the light transmittance of a wavelength of 420 nm is preferably 70% or more. That is, the ultraviolet absorbing composition of the present invention preferably absorbs the wavelength of the UV-A region efficiently and is preferably excellent in the light transmittance in the visible light region, and by having such physical properties, Yellowing and coloring of the ultraviolet absorbing composition can be suppressed.
  • the ultraviolet absorbing compound used in the ultraviolet absorbing composition of the present invention is not particularly limited as long as it has a maximum absorption wavelength of 380 nm or less and satisfies the physical properties defined in the present invention, but it is not particularly limited. From the viewpoint, a compound having a molecular weight in the range of 400 to 3,000 is preferable, more preferably 500 to 2,500, and still more preferably a compound having a molecular weight in the range of 600 to 2,000.
  • the ultraviolet light absorbing compound is preferably a compound having at least one merocyanine skeleton in the molecule, and more preferably a compound having two or more merocyanine skeletons in the molecule.
  • Examples of UV-absorbing compounds having a merocyanine skeleton in the molecule that can be used in the present invention include the exemplified compounds II-7 and II-8 described in JP-A-57-157245 and JP-A-2008-81445.
  • the exemplified compounds I-2, I-10, I-20 and the like described in the publication can be mentioned, and such compounds can be applied to the present invention.
  • R 11 , R 12 and R 13 each independently represent a hydrogen atom, an aliphatic group, an aromatic group or a heterocyclic group bonded via a carbon atom
  • L 11 to L 14 each independently represent Represents a single bond or a divalent group
  • -X- represents -O-, -S-, -N- or -C (R 14 )-
  • R 14 represents a hydrogen atom or a substituent.
  • n 11 and n 12 are each independently an integer of 0 or more. However, when n 11 and n 12 are 1 or more at the same time, the order of arrangement of structural units forming a chain structure in [] is arbitrary.
  • n 13 represents 0 when -X- is -O- or -S-, and 1 when -X- is -N- or -C (R 14 )-.
  • Two or more substituents of R 11 , R 12 , R 13 , R 14 , L 11 , L 12 , L 13 and L 14 may combine with each other to form a ring.
  • R 31 and R 32 each independently represent a substituent having a ⁇ p value of 0.20 or more
  • R 33 , R 34 and R 35 each independently represent a hydrogen atom, an aliphatic group or an aromatic group. Or a heterocyclic group linked by a carbon atom.
  • ⁇ p value used for the definition of the substituent in the above general formula (Ia) is L.I. P.
  • Substituent constants determined by the Hammett's law include ⁇ p values and ⁇ m values, and these values are described in many general books. A. Dean, "Lange's Handbook of Chemistry", 12th edition, 1979 (Mc Graw-Hill) and "Regional Development of Chemistry", No. 122, pp. 96-103, 1979 (Nanegendo).
  • R 31 and R 32 are defined by Hammett's substituent constant ⁇ p value, but they do not mean that they are limited to only certain substituents having known values in the literature described in these documents. Of course, even if the document is unknown, it is included as long as it is included in the range when it is measured based on the Hammett law.
  • the aliphatic group such as an aliphatic group in the general formula (Ia) means an alkyl group, a substituted alkyl group, an alkenyl group, a substituted alkenyl group, an alkynyl group, a substituted alkynyl group, an aralkyl group and a substituted aralkyl group.
  • the alkyl group may be branched or may form a ring.
  • the number of carbon atoms of the alkyl group is preferably 1 to 20, and more preferably 1 to 18.
  • the definition of the alkyl moiety of the substituted alkyl group is the same as the above alkyl group.
  • the alkenyl group may be branched or may form a ring.
  • the number of carbon atoms of the alkenyl group is preferably 2 to 20, and more preferably 2 to 18.
  • the definition of the alkenyl moiety of the substituted alkenyl group is the same as the above alkenyl group.
  • the alkynyl group may be branched or may form a ring.
  • the number of carbon atoms in the alkynyl group is preferably 2 to 20, and more preferably 2 to 18.
  • the definition of the alkynyl moiety of the substituted alkynyl group is the same as the above alkynyl group.
  • the definition of the alkyl part of the aralkyl group and the substituted aralkyl group is the same as the above alkyl group.
  • the definition of the aryl part of the aralkyl group and the substituted aralkyl group is the same as the following aryl group.
  • Examples of the substituent of the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group and the alkyl moiety of the substituted aralkyl group include a halogen atom (eg, chlorine atom, bromine atom, iodine atom), an alkyl group [linear, branched, cyclic Represents a substituted or unsubstituted alkyl group.
  • a halogen atom eg, chlorine atom, bromine atom, iodine atom
  • alkyl groups preferably alkyl groups having 1 to 30 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, t-butyl, n-octyl, eicosyl, 2-chloroethyl, 2-cyanoethyl, 2-ethylhexyl
  • Cycloalkyl group preferably, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, such as cyclohexyl, cyclopentyl, 4-n-dodecylcyclohexyl
  • bicycloalkyl group preferably, 5 to 30 carbon atoms
  • a substituted or unsubstituted bicycloalkyl group that is, a monovalent group obtained by removing one hydrogen atom from a bicycloalkane having 5 to 30 carbon atoms, for example, bicyclo [1.2.2] heptane-2-yl,
  • octan-3-yl a tricyclo structure having more ring structures Domo is intended to cover.
  • the alkyl group (for example, the alkyl group of the alkylthio group) in the substituents described below also represents an alkyl group having such a concept. ]
  • alkenyl group [a linear, branched, cyclic substituted or unsubstituted alkenyl group is represented. They are alkenyl groups (preferably substituted or unsubstituted alkenyl groups having 2 to 30 carbon atoms, such as vinyl, allyl, prenyl, geranyl, oleyl), cycloalkenyl groups (preferably, substitution or 3 to 30 carbon atoms)
  • An unsubstituted cycloalkenyl group that is, a monovalent group obtained by removing one hydrogen atom of a cycloalkene having 3 to 30 carbon atoms, such as 2-cyclopenten-1-yl, 2-cyclohexen-1-yl), Bicycloalkenyl group (substituted or unsubstituted bicycloalkenyl group, preferably a substituted or unsubstituted bicycloalkenyl group having a carbon number of 5 to 30, ie, a monovalent compound from which one
  • alkynyl group preferably, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, for example, ethynyl, propargyl, trimethylsilylethynyl group
  • An aryl group (preferably a substituted or unsubstituted aryl group having a carbon number of 6 to 30, such as phenyl, p-tolyl, naphthyl, m-chlorophenyl, o-hexadecanoylaminophenyl), a heterocyclic group (preferably 5 or 6) Or a monovalent group obtained by removing one hydrogen atom from a substituted or unsubstituted aromatic or non-aromatic heterocyclic compound, and more preferably a 5- to 6-membered aromatic having 3 to 30 carbon atoms
  • 2-furyl, 2-thienyl, 2-pyrimidinyl, 2-benzothiazolyl cyano group, hydroxyl group, nitro group, carboxyl group, alkoxy group (preferably having 1 to 30 carbon atoms)
  • a substituted or unsubstituted alkoxy group for example, methoxy, ethoxy, isopropoxy, t-butoxy, n-oc
  • Silyloxy group preferably, a C3-C20 silyloxy group such as trimethylsilyloxy, t-butyldimethylsilyloxy
  • heterocyclic oxy group preferably, a C2-C30 substituted or unsubstituted heterocyclic oxy group Group, 1-phenyltetrazole-5-oxy, 2-tetrahydropyranyloxy
  • acyloxy group preferably formyloxy group, substituted or unsubstituted alkylcarbonyloxy group having 2 to 30 carbon atoms, 6 to 30 carbon atoms
  • a substituted or unsubstituted arylcarbonyloxy group for example, formyloxy, acetyloxy, pivaloyloxy, stearoyloxy, benzoyloxy, p-methoxyphenylcarbonyloxy
  • carbamoyloxy group preferably having a carbon number of 1 to 30 or less; Conversion of the carbamoyl group, for example, N,
  • Alkoxycarbonyloxy group preferably, a substituted or unsubstituted alkoxycarbonyloxy group having 2 to 30 carbon atoms, such as methoxycarbonyloxy, ethoxycarbonyloxy, t-butoxycarbonyloxy, n-octylcarbonyloxy), aryloxycarbonyloxy group (Preferably, a substituted or unsubstituted aryloxycarbonyloxy group having 7 to 30 carbon atoms, for example, phenoxycarbonyloxy, p-methoxyphenoxycarbonyloxy, pn-hexadecyloxyphenoxycarbonyloxy), amino group (preferably Is an amino group, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted anilino group having 6 to 30 carbon atoms, for example, amino, methylamino, dimethylamino, Lino, N-methyl-anil
  • Aminocarbonylamino group preferably, substituted or unsubstituted aminocarbonylamino having 1 to 30 carbon atoms, such as carbamoylamino, N, N-dimethylaminocarbonylamino, N, N-diethylaminocarbonylamino, morpholinocarbonylamino
  • An alkoxycarbonylamino group preferably a substituted or unsubstituted alkoxycarbonylamino group having a carbon number of 2 to 30, for example, methoxycarbonylamino, ethoxycarbonylamino, t-butoxycarbonylamino, n-octadecyloxycarbonylamino, N-methyl-methoxy A carbonylamino
  • an aryloxycarbonylamino group preferably, a substituted or unsubstituted aryloxycarbonylamino group having a carbon number of 7 to 30, for example, P-chlorophenoxycarbonylamin
  • alkyl or arylsulfonylamino group preferably a substituted or unsubstituted alkylsulfonylamino having 1 to 30 carbon atoms, a substituted or unsubstituted arylsulfonylamino having 6 to 30 carbon atoms, eg, methylsulfonylamino, butylsulfonylamino, phenyl Sulfonylamino, 2,3,5-trichlorophenylsulfonylamino, p-methylphenylsulfonylamino), mercapto group, alkylthio group (preferably, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, such as methylthio, ethylthio, n-hexadecylthio), an arylthio group (preferably a substituted or unsubstituted arylthio having 6 to 30
  • a sulfamoyl group (preferably a substituted or unsubstituted sulfamoyl group having 0 to 30 carbon atoms, for example, N-ethylsulfamoyl, N- (3-dodecyloxypropyl) sulfamoyl, N, N-dimethylsulfamoyl, N- Acetylsulfamoyl, N-benzoylsulfamoyl, N- (N'-phenylcarbamoyl) sulfamoyl), sulfo group, alkyl and arylsulfinyl group (preferably, a substituted or unsubstituted alkylsulfinyl group having 1 to 30 carbon atoms) 6 to 30 substituted or unsubstituted arylsulfinyl groups, for example, methylsulfinyl, ethylsulfinyl, phen
  • Acyl group (preferably formyl group, substituted or unsubstituted alkylcarbonyl group having 2 to 30 carbon atoms, substituted or unsubstituted arylcarbonyl group having 7 to 30 carbon atoms, substituted or unsubstituted carbon having 4 to 30 carbon atoms Heterocyclic carbonyl group bonded to a carbonyl group at an atom, such as acetyl, pivaloyl, 2-chloroacetyl, stearoyl, benzoyl, pn-octyloxyphenylcarbonyl, 2-pyridylcarbonyl, 2-furylcarbonyl), aryl An oxycarbonyl group (preferably, a substituted or unsubstituted aryloxycarbonyl group having a carbon number of 7 to 30, for example, phenoxycarbonyl, o-chlorophenoxycarbonyl, m-nitrophenoxycarbonyl, p-t-butylphenoxy
  • Aryl and heterocyclic azo groups preferably substituted or unsubstituted arylazo groups having 6 to 30 carbon atoms, substituted or unsubstituted heterocyclic azo groups having 3 to 30 carbon atoms, for example, phenylazo, p-chlorophenylazo, 5- Ethylthio-1,3,4-thiadiazol-2-ylazo), imide group (preferably N-succinimide, N-phthalimide), phosphino group (preferably C 2-30 substituted or unsubstituted phosphino group, For example, dimethyl phosphino, diphenyl phosphino, methyl phenoxy phosphino), phosphinyl group (preferably, a substituted or unsubstituted phosphinyl group having 2 to 30 carbon atoms, for example, phosphinyl, dioctyl oxyphosphinyl, diethoxy phosphinyl) Le), phosphin
  • those having a hydrogen atom may be removed and further substituted with the above group.
  • Examples of such functional groups include alkylcarbonylaminosulfonyl group, arylcarbonylaminosulfonyl group, alkylsulfonylaminocarbonyl group and arylsulfonylaminocarbonyl group. Examples thereof include methylsulfonylaminocarbonyl, p-methylphenylsulfonylaminocarbonyl, acetylaminosulfonyl and benzoylaminosulfonyl group.
  • the example of the substituent of the aryl part of a substituted aralkyl group is the same as the example of the substituent of the following substituted aryl group.
  • the aromatic group in the present specification such as the aromatic group in the general formula (Ia) means an aryl group and a substituted aryl group.
  • these aromatic groups may be fused with an aliphatic ring, another aromatic ring or a heterocyclic ring.
  • the number of carbon atoms in the aromatic group is preferably 6 to 40, more preferably 6 to 30, and even more preferably 6 to 20.
  • the aryl group is preferably phenyl or naphthyl, particularly preferably phenyl.
  • the definition of the aryl part of the substituted aryl group is the same as the above-mentioned aryl group.
  • Examples of the substituent of the substituted aryl group are the same as those listed above as examples of the substituent of the alkyl moiety of the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group and the substituted aralkyl group.
  • the heterocyclic group in the present specification preferably contains a 5- or 6-membered saturated or unsaturated heterocyclic ring.
  • the heterocyclic ring may be fused with an aliphatic ring, an aromatic ring or another heterocyclic ring.
  • heteroatoms of the heterocyclic ring include B, N, O, S, Se and Te.
  • hetero atoms N, O and S are preferable.
  • the hetero ring is preferably a carbon atom having a free valence (monovalent) (the hetero ring group is bonded at a carbon atom).
  • the carbon number of the heterocyclic group is preferably 1 to 40, more preferably 1 to 30, and still more preferably 1 to 20.
  • saturated heterocyclic ring examples include pyrrolidine ring, morpholine ring, 2-bora-1,3-dioxolane ring and 1,3-thiazolidine ring.
  • unsaturated heterocyclic rings examples include imidazole ring, thiazole ring, benzothiazole ring, benzoxazole ring, benzotriazole ring, benzoselenazole ring, pyridine ring, pyrimidine ring and quinoline ring.
  • the heterocyclic group may have a substituent.
  • substituents are the same as those exemplified as the substituent of the alkyl moiety of the substituted alkyl group, the substituted alkenyl group, the substituted alkynyl group and the substituted aralkyl group.
  • an ultraviolet absorbing compound represented by the following general formula (Ib) can be mentioned.
  • R 11 to R 13 , L 11 to L 14 , -X-, n 11 , n 12 , R 33 , R 34 and R 35 each represents R 11 to R 11 in the general formula (Ia) It is synonymous with R 13 , L 11 to L 14 , -X-, n 11 , n 12 , R 33 , R 34 and R 35 respectively.
  • R36 and R37 each independently represent an aliphatic group, an aromatic group or a heterocyclic group bonded to one another via a carbon atom.
  • R 11 represents a substituent.
  • substituents include the same as those exemplified as the substituent of the aforementioned substituted alkyl group, substituted alkenyl group, substituted alkynyl group and alkyl moiety of the substituted aralkyl group.
  • R 11 , R 12 and R 13 each is preferably a hydrogen atom, an alkyl group, an alkenyl group, an aralkyl group or an aryl group, more preferably a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an alkenyl having 2 to 20 carbon atoms Group, an aralkyl group having 7 to 20 carbon atoms, and an aryl group having 6 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, and 7 to 10 carbon atoms.
  • Aralkyl group and aryl group having 6 to 10 carbon atoms more preferably alkyl group having 1 to 10 carbon atoms, aralkyl group having 7 to 10 carbon atoms and aryl group having 6 to 10 carbon atoms, more preferably Is an alkyl group having 1 to 10 carbon atoms or an aralkyl group having 7 to 10 carbon atoms, more preferably an aralkyl group having 7 to 10 carbon atoms, and most preferably benzyl.
  • It is a radical. It is also preferred that all of R 11 , R 12 and R 13 are identical.
  • Each of L 11 , L 12 and L 13 is preferably a single bond, alkylene, arylene, a divalent group consisting of a combination of alkylene and arylene, a divalent group consisting of alkylene and an oxygen atom, and a divalent group consisting of arylene and an oxygen atom Group and a divalent group consisting of alkylene, arylene and oxygen atom, more preferably a single bond, alkylene having 1 to 20 carbons, arylene having 6 to 20 carbons, and alkylene having 7 to 20 carbons in total and arylene
  • a divalent group consisting of a combination of alkylene and arylene having 7 to 10 carbon atoms in total, a divalent group consisting of alkylene and 2 to 10 carbon atoms, and arylene having 7 to 10 carbon atoms and an oxygen atom It is a divalent group, more preferably a single bond, an alkylene having 2 to 10 carbon atoms, an arylene having 6 to 10 carbon atoms, a divalent group consisting of an alkylene having 2 to 10 carbon atoms and an oxygen atom, and still more preferably A single bond, an alkylene having 2 to 10 carbon atoms, and a divalent group consisting of an alkylene having 2 to 10 carbon atoms and an oxygen atom, and most preferably a single bond or an alkylene having 2 to 10 carbon atoms.
  • the total number of carbon atoms in the linear portion of L 11 and L 12 , L 11 and X, and L 13 and X is 2 or more.
  • L 14 when X is —C (R 14 ) — is the same as for L 11 described above.
  • L 14 when X is —N— is preferably alkylene, arylene, a divalent group consisting of a combination of alkylene and arylene, a divalent group consisting of alkylene and an oxygen atom, and a divalent group consisting of arylene and an oxygen atom
  • a divalent group consisting of an alkylene, a substituted or unsubstituted arylene and an oxygen atom and more preferably an alkylene having 1 to 20 carbon atoms, an arylene having 6 to 20 carbon atoms, and an alkylene having 7 to 20 carbon atoms in total.
  • a divalent group consisting of a combination of alkylene and arylene having 7 to 10 carbon atoms in total, a divalent group consisting of alkylene and 2 to 10 carbon atoms, and arylene having 7 to 10 carbon atoms and an oxygen atom It is a divalent group, more preferably an alkylene having 2 to 10 carbon atoms, an arylene having 6 to 10 carbon atoms, a divalent group consisting of an alkylene having 2 to 10 carbon atoms and an oxygen atom, and still more preferably 2 It is a divalent group consisting of an alkylene of 10 and an alkylene of 2 to 10 carbon atoms and an oxygen atom, and most preferably an alkylene of 2 to 10 carbon atoms.
  • X is -N- and -C (R 14 )-, and more preferred is -C (R 14 )-.
  • R 14 is preferably a hydrogen atom, halogen atom, alkyl group, alkenyl group, alkynyl group, aryl group, cyano group, hydroxyl group, carboxyl group, alkoxy group, aryloxy group, silyloxy group, acyloxy group, carbamoyloxy group, alkoxy Carbonyloxy, aryloxycarbonyloxy, amino, acylamino, aminocarbonylamino, alkoxycarbonylamino, aryloxycarbonylamino, sulfamoylamino, alkyl and arylsulfonylamino, mercapto, alkylthio , Arylthio group, sulfamoyl group, sulfo group, alkyl and arylsulfinyl group, alkyl and arylsulfonyl group, acyl group, aryloxycarbonyl group, alkoxy A carbonyl group, a
  • R 15 has the same meaning as the above-mentioned R 12, and preferred ranges are also the same.
  • L 15 has the same meaning as L 14 described above, and the preferred range is also the same.
  • n 11 is preferably 0 to 20, more preferably 0 to 10, still more preferably 0 to 5, still more preferably 1 to 3, still more preferably 1 to 2, and most preferably It is 1.
  • the n 12 is preferably 0 to 20, more preferably 0 to 10, still more preferably 0 to 5, still more preferably 0 to 3, and most preferably 0 to 1.
  • R 31 and R 32 each independently represent a substituent having a ⁇ p value of 0.20 or more.
  • R 31 and R 32 each is preferably a substituent having a ⁇ p value of 0.30 or more, more preferably an alkane or arylenesulfonyl group, an acyl group, an arylcarbonyl group, a cyano group, an alkoxycarbonyl group or an aryloxycarbonyl group And more preferably arenesulfonyl groups having 6 to 20 carbon atoms (eg, benzenesulfonyl group, p-toluenesulfonyl group, p-chlorobenzenesulfonyl group, naphthalenesulfonyl group), acyl groups having 1 to 20 carbon atoms (eg, formyl group) Group, acetyl group, propionyl group), arylcarbonyl group having 7 to 20 carbon atoms, nitrile group
  • R 33 , R 34 and R 35 each independently represent a hydrogen atom, an aliphatic group, an aromatic group and a heterocyclic group bonded by a carbon atom, preferably a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, and a carbon number It is an aryl group of 6 to 10, more preferably a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, still more preferably a hydrogen atom, a methyl group or an ethyl group, and most preferably a hydrogen atom.
  • R 36 and R 37 each independently represent an aliphatic group, an aromatic group and a heterocyclic group bonded via a carbon atom, preferably an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 10 carbon atoms, More preferably, they are an alkyl group having 3 to 8 carbon atoms and an aryl group having 6 to 8 carbon atoms, and more preferably a 2-ethylhexyl group, an octyl group, a phenyl group and a benzyl group. Most preferably R 36 is a phenyl group, most preferably R 37 is an octyl group.
  • the UV absorbing compound represented by the general formula (Ia) suitably used in the present invention can be synthesized according to the scheme shown in the following (Formula 1).
  • R 11 , R 12 and R 13 each independently represent a hydrogen atom, an aliphatic group, an aromatic group, or a heterocyclic group bonded by a carbon atom
  • L 11 ⁇ L 14 each independently represents a single bond or a divalent linking group
  • -X- represents -O-, -S-, -N- or -C (R 14 )-
  • R 14 represents a hydrogen atom or a substituent.
  • n 11 and n 12 are each independently an integer of 0 or more. However, when n 11 and n 12 are 1 or more simultaneously, the order of arrangement of the structural units forming the chain structure in [] is arbitrary.
  • n 13 is 0 when -X- is -O- or -S-, and 1 when -X- is -N- or -C (R 14 )-.
  • R 11 , R 12 , R 13 , R 14 , L 11 , L 12 , L 13 and L 14 may be bonded to each other to form a ring.
  • L v represents a group containing at least one carbon atom
  • C * represents a monovalent group containing a carbon atom
  • C * represents a nitrogen atom in the general formula (II)
  • the substitution results in the formation of a compound of general formula (I).
  • L v has the same meaning as L v in the general formula (III).
  • one or more compounds represented by general formula (III) are used, and when two or more are used, C * in the general formula (I) may be the same or different.
  • the ultraviolet absorbing compound represented by the general formula (Ia) (corresponding to the compound represented by the general formula (I) in the above scheme) is obtained by performing the substitution reaction step represented by the above (formula 1) Can.
  • amide solvents eg, N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone
  • sulfone solvents eg, sulfolane
  • sulfoxide solvents Form example, dimethyl sulfoxide
  • ureido solvents for example, tetramethylurea
  • alcohol solvents for example, methanol, ethanol, isopropanol
  • ether solvents for example, dioxane, cyclopentyl methyl ether
  • hydrocarbon solvents for example, Toluene, xylene, n-decane
  • halogen solvents eg, tetrachloroethane, chlorobenzene
  • pyridine solvents eg, pyridine, ⁇ -picoline, 2,6-lutidine
  • nitrile solvents eg, acetonitrile
  • Ester solvent for example,
  • solvents preferred are sulfone solvents, sulfoxide solvents, alcohol solvents, ether solvents, hydrocarbon solvents, halogen solvents, and aqueous solvents, and more preferably alcohol solvents and ether solvents And hydrocarbon solvents, halogen solvents, and aqueous solvents, more preferably alcohol solvents, hydrocarbon solvents, and aqueous solvents. It is most preferable to carry out the reaction in a mixed solvent of an alcohol solvent and a water solvent.
  • the reaction temperature in the above substitution reaction is preferably 0 to 250 ° C., more preferably 20 to 200 ° C., still more preferably 40 to 150 ° C., still more preferably 60 to 130 ° C., further preferably 70 to 110 ° C.
  • the compound represented by General Formula (IV) which is a by-product thereof is obtained, so the reaction is completed. Thereafter, a purification step may be performed to remove byproducts.
  • the scheme represented by the above (formula 1) by appropriately selecting the starting material, the solvent and the like, the following compounds included in the ultraviolet absorbing compound represented by the general formula (Ia) can be synthesized .
  • the ultraviolet absorbing compound used in the ultraviolet absorbing composition of the present invention may be used alone or in combination of two or more.
  • the content of the ultraviolet absorbing compound is preferably 1.0 ⁇ 10 ⁇ 7 mol / g to 1.0 ⁇ 10 ⁇ 3 mol / g with respect to the ultraviolet absorbing composition.
  • the content in terms of mass is preferably 5 ⁇ 10 ⁇ 4 to 1.0 ⁇ 10 ⁇ 1 g, more preferably 5 ⁇ 10 ⁇ 4 to 1.0 ⁇ 10 ⁇ 1 g, of the ultraviolet absorbing compound contained in 1 g of the ultraviolet absorbing composition of the present invention. Is from 1.0 ⁇ 10 -3 to 8.0 ⁇ 10 -2 g, more preferably from 5.0 ⁇ 10 -3 to 7.0 ⁇ 10 -2 g.
  • the ultraviolet ray absorbing composition of the present invention is required to contain the above-mentioned ultraviolet ray absorbing compound as defined in the present invention, but other components used in combination with the ultraviolet ray absorbing compound are optional. There is no limit. However, the other components need to be appropriately selected within the range that can achieve the above-mentioned physical properties, that is, light transmittance when the film is formed to a thickness of 10 ⁇ m.
  • the ultraviolet absorbing composition of the present invention can be applied to fibers, resin molded articles, coating agents, paints, resin films and the like as an ultraviolet absorbing resin composition using a resin as a medium. It can apply also to ultraviolet absorptivity glass, its molded article, etc. as an ultraviolet absorptivity inorganic material which makes inorganic materials, such as glass, a medium. Furthermore, the base of human skin or hair cosmetics and medical preparations can be used as a medium.
  • the medium include solvents, resins, and inorganic materials.
  • the organic solvent which is a medium used in the present invention include hydrocarbons such as pentane, hexane and octane, aromatics such as benzene, toluene and xylene, and ethers such as diethyl ether and methyl-t-butyl ether.
  • Alcohols such as methanol, ethanol and isopropanol, Esters such as acetone, ethyl acetate and butyl acetate, Ketones such as methyl ethyl ketone, Nitriles such as acetonitrile and propionitrile, N, N-dimethylformamide, N, N-dimethyl form Amides such as acetamide and N-methyl pyrrolidone, sulfoxides such as dimethyl sulfoxide, amines such as triethylamine and tributylamine, carboxylic acids such as acetic acid and propionic acid, halogens such as methylene chloride and chloroform Tetrahydrofuran, heterocyclic ring system, such as pyridine, and the like.
  • Esters such as acetone, ethyl acetate and butyl acetate, Ketones such as methyl ethyl ketone, Nitriles such as acetonitrile
  • organic solvent a high boiling point organic solvent can be used according to the purpose.
  • high-boiling organic solvents include phosphoric acid esters, phosphonic acid esters, benzoic acid esters, phthalic acid esters, fatty acid esters, carbonic acid esters, amides, ethers, halogenated hydrocarbons, alcohols and paraffins.
  • thermoplastic resin examples include polyethylene resins, polypropylene resins, poly (meth) acrylate resins, polystyrene resins, styrene-acrylonitrile resins, acrylonitrile-butadiene-styrene resins, polyvinyl chloride resins, Polyvinylidene chloride resin, polyvinyl acetate resin, polyvinyl butyral resin, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol resin, polyethylene terephthalate resin (PET), polybutylene terephthalate resin (PBT), liquid crystal polyester Resin (LCP), polyacetal resin (POM), polyamide resin (PA), polycarbonate resin, polyurethane resin, polyphenylene sulfide resin (PPS), etc., and one
  • these resins are also used as thermoplastic molding materials in which natural resin contains fillers such as glass fibers, carbon fibers, semi-carbonized fibers, cellulose fibers, glass beads, and flame retardants. If necessary, additives for resins conventionally used, for example, fine particles of polyolefin resin fine powder, polyolefin wax, ethylene bisamide wax, metal soap and the like may be used alone or in combination.
  • thermosetting resin an epoxy resin, a melamine resin, unsaturated polyester resin etc. are mentioned, for example.
  • fillers such as glass fiber, carbon fiber, semi-carbonized fiber, cellulose fiber, glass beads, and a flame retardant are contained. It can also be used as a thermosetting molding material.
  • examples of the inorganic material include titanium dioxide, zinc oxide, aluminum oxide, glass, calcium carbonate, calcined clay, talc, silica, diatomaceous earth, alumina, magnesium oxide, aluminum hydroxide, magnesium hydroxide, uncalcined clay and the like.
  • the ultraviolet absorbing composition of the present invention based on these solvents, resins, and inorganic materials, they may be dissolved or dispersed directly in these bases according to the physical properties of the ultraviolet absorbing compound to be used. After being dissolved in an appropriate solvent, it may be prepared by adding to a base.
  • an ultraviolet absorbing compound is added to the base of external preparations which are various cosmetic and pharmaceutical preparations, in the range satisfying the above physical properties.
  • the other components of the base used in such cosmetics and external medicines as long as the formulation is excellent in usability and safety applicable to skin and hair, and those skilled in the art It can be prepared according to the purpose according to well-known techniques.
  • components that can be used as a medium (base) oils and fats and waxes generally used as a base for cosmetics and pharmaceutical preparations, hydrocarbon oils, fatty acids, alcohols, esters, silicones, powders, etc. It can be mentioned.
  • UV absorbing compounds are lipophilic, they can be prepared by adding the UV absorbing compound to the oil phase when it is blended in the base of these cosmetic and pharmaceutical preparations.
  • the ultraviolet ray absorbing composition of the present invention in addition to the specific ultraviolet ray absorber, various compounds such as the above base may be used in combination.
  • the external preparation is used in combination when applying the ultraviolet absorbing composition of the present invention to various preparations for protecting the skin of human or animal or hair from ultraviolet rays such as cosmetic compositions and pharmaceutical compositions.
  • the various acceptable materials will be described.
  • the ultraviolet absorbing composition of the present invention is suitable, for example, for skin cosmetic compositions, hair cosmetic compositions, pharmaceutical compositions for use on the skin or hair, and the like.
  • the other components are not particularly limited as long as the formulation is excellent in safety, and according to techniques well known to those skilled in the art, It can be prepared according to the purpose.
  • fats and oils, waxes, hydrocarbon oils, fatty acids, alcohols, esters, silicones, powders, etc. which can be used as a base material of the ultraviolet light absorbing composition can be used as active ingredients of the composition.
  • select saccharides, animal and plant extracts, amino acids, vitamins, surfactants, colorants, etc. that can be used to adjust the physical properties of the substrate, improve the appearance, or improve the feel. It can be used.
  • organic or inorganic ultraviolet absorbing compounds other than the ultraviolet absorbing compounds compatible with the above conditions.
  • a germicide, an antiseptic, an antioxidant, a sequestering agent, a fragrance, a coloring agent, an additive as an active ingredient contained in other cosmetics and the like can also be used.
  • various components which can be used when applying the ultraviolet absorbing composition of the present invention to humans and animals will be sequentially described.
  • fats and oils As fats and oils, it is used as a base of cosmetic oil, an oil phase component of cream, an emollient agent, a binder of powder of make-up cosmetic, and a fatliquor / feel modifier of shampoo and rinse.
  • As fats and oils which can be used for this invention what has a triglyceride, ie, the triester of a fatty acid and glycerol, is mentioned as a main component, Usually, the wax which is ester of a higher fatty acid and a higher alcohol is distinguished. Fats and oils are widely present in the natural flora and fauna, and are used in various industries including food. Depending on the properties at normal temperature, the liquid is called fatty oil and the solid one is called fat.
  • oils mineral oils (liquid paraffin); vegetable oils (eg sweet almond oil, macadamia oil, blackcurrant seed oil, jojoba oil, olive oil, castor oil, sunflower oil etc.); synthetic oils (eg perhydrosqualene) Fatty alcohols, fatty acids or fatty esters (eg C12-C15 alkyl benzoate, octyl palmitate, lanolinic acid sold by the company Witco under the trade name "Witconol TN" or "Finsorb TN”) Triglycerides, including isopropyl, capric / caprylic, or dicaprylyl carbonate sold under the name "Cetiol CC" from Cognis, or oxyethylenated or oxypropyleneified fatty esters and ethers Silicone oils (cyclomethicone, polydimethylsiloxanes or PDMS); can be given or polyalkylenes; fluorinated oils.
  • mineral oils liquid paraffin
  • vegetable oils
  • wax esters are mainly composed of esters of higher fatty acids and higher alcohols (wax esters), and examples thereof include beeswax, lanolin, carnauba wax, candelilla wax and jojoba oil.
  • wax esters there are substances which are conventionally referred to as waxes depending on the components or depending on physical conditions, waxes used in cosmetics are mainly natural wax esters.
  • waxy compounds include hydrogenated castor oil, polyethylene wax, and polymethylene wax, for example, those sold under the name “Cirebelle 303” by Sasol.
  • Hydrocarbons are a general term for compounds consisting of carbon and hydrogen, and are roughly classified into chain hydrocarbons and cyclic hydrocarbons according to the arrangement of carbon atoms. Chain-like hydrocarbons are often used as cosmetic raw materials. There are petroleum based, naturally occurring mineral based, synthetic based, animal based and plant based.
  • hydrocarbon oil mineral oil (light oil or heavy oil), petrolatum (yellow or white), microcrystalline wax, paraffinic compound and isoparaffinic compound, hydrogenated isoparaffinic molecule such as polydecene and polybutene, hydrogenated polyisobutene, squalane , Isohexadecane, isododecane, and others from plant kingdom and animal kingdom.
  • the fatty acids are roughly classified into natural fatty acids and synthetic fatty acids, and natural fatty acids are produced from animal and vegetable fats and oils.
  • Synthetic fatty acids are mainly liquid, and branched fatty acids are often used in cosmetics. Specifically, for example, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, isostearic acid and the like can be mentioned.
  • Alcohols are compounds represented by the general formula R-OH. Alcohols in which the number of hydroxyl groups is one, two, three, etc. are referred to as monohydric alcohols, dihydric alcohols (glycols), trihydric alcohols and the like. Moreover, what the hydroxyl group substituted to the side chain of aromatic hydrocarbon is called aromatic alcohol.
  • a cosmetic base a surfactant raw material, and an oil component, a higher alcohol having about 8 to 24 carbon atoms is often used.
  • alcohols usable in cosmetics include cetyl alcohol, stearyl alcohol, cetostearyl alcohol (mixture of cetyl and stearyl), oleyl alcohol, octyl dodecanol and the like, and it has 6 to 18 carbon atoms, preferably 8 to 10 Guerbet alcohol based on the aliphatic alcohol having individual, benzoate of alcohol having 12 to 15 carbon atoms, acetylated lanolin alcohol and the like can be mentioned.
  • Esters are compounds obtained by the dehydration reaction of a fatty acid and an alcohol.
  • Examples of ester oils are isopropyl myristate, isopropyl palmitate, isopropyl stearate, isopropyl isostearate, isopropyl oleate, n-butyl stearate, n-hexyl laurate, n-decyl oleate, isooctyl stearate, stearic acid Isononyl, isononyl isononate, 2-ethylhexyl palmitate, 2-hexyl laurate, 2-hexyldecyl stearate, 2-octyldodecyl palmitate, oleyl oleate, oleyl erucate, erucyl oleate, erucile erucyl, octanoate Cetearyl, cetyl palmitate, cetyl
  • Silicone oil and fluorine oil is a synthetic polymer in which organically attached silicon and oxygen are alternately linked by a chemical bond, and is used in cosmetics because it is stable.
  • Silicone (dimethylpolysiloxanes), organic substituted polysiloxane and the like can be used, and specific examples thereof include dimethylpolysiloxane, methylphenylpolysiloxane, cyclic silicone, and further, amino-, fatty acid-, alcohol-
  • polyether-, epoxy-, fluorine-, glycoside- and / or alkyl-modified silicone compounds and the like may be liquid at room temperature or may be in resinous form and may be used depending on the dosage form.
  • General-purpose silicones include linear polysiloxane, dimethicone (eg, 200 oil manufactured by Dow Corning), cyclic silicone oil, cyclopentasiloxane volatiles (eg, 345 oil manufactured by Dow Corning), phenyltrimethicone (For example, Dow Corning Co., 556 oil), and simethicone, which is a mixture of dimethicone having an average chain length of 200 to 300 dimethylsiloxane units and hydrogenated silicate, may also be used. .
  • fluorine oil or perfluorinated oil examples include perfluorohexane, dimethylcyclohexane, ethylcyclopentane, polyperfluoromethyl isopropyl ether and the like.
  • polyhydric alcohols can be used for the ultraviolet light absorbing composition for adjusting the viscosity or improving the moisture retention.
  • a polyhydric alcohol is a compound having two or more hydroxyl groups in the molecule, and is called a dihydric or trihydric alcohol depending on the number of hydroxyl groups.
  • the use of polyhydric alcohol in cosmetics is also used as a moisturizer for skin care cosmetics, shampoos, rinses and the like.
  • Examples of polyhydric alcohols include ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, glycerin, polyglycerin, 3-methyl-1,3-butanediol, 1,3-butylene glycol and the like.
  • saccharides saccharides having physiological activity and pharmacological activity and derivatives thereof are developed and used as medicines.
  • the use for cosmetics is often used as a moisturizer and skin softener in skin care cosmetics and hair care cosmetics.
  • saccharides include sorbitol, D-sorbit, glucitol, mannitol, glucose, sucrose, lactose, maltose, maltitol, trehalose and the like.
  • various polymer compounds can be used as a substrate or as viscosity adjustment.
  • a high molecular compound is called a thickener, an emulsifier, a moisturizer, a film forming agent, etc. by the function in a composition.
  • carboxyvinyl polymers eg, carbopols (carbomers) and pemulen (copolymers of acrylates and alkyl acrylates having 10 to 30 carbon atoms); polyacrylamides [Eg from Seppic, Sepigel 305 (CTFA name: polyacrylamide / C13-C14 isoparaffin / Laureth 7), Simulgel 600 (CTFA name: acrylamide / acryloyldimethyl taurate] Sodium copolymer / crosslinked copolymer sold under the name of isohexadecane / polysorbate 80)]; cross-linked or optionally neutralized 2-acrylamido-2-methane Polymers and copolymers of polypropanesulfonic acid (eg poly (2-acrylamido-2-methylpropanesulfonic acid) (CTFA name: polyacryloyl sold by Hoechst under the trade name “Hostacerin AMPS”) Ammonium dimethyl taurate
  • synthetic polymers such as poly (alkyl acrylates) sold by Landec under the names "Intelamer IPA 13-1" and “Intellimer IPA 13-6”
  • modified clays such as hectorite and its derivatives, such as esters (alkyl having 10 to 30 carbon atoms), for example the products sold under the name "Bentone”.
  • Surfactants are useful, for example, when the ultraviolet absorbing composition is used as an emulsifying composition. It may be called an emulsifier, a solubilizer, a dispersing agent, a spreading agent etc. from a use.
  • Examples of surfactants that can be used in the present invention include aliphatic alcohol polyglycol ether sulfate, monoglyceride sulfate, mono- and / or di-alkyl sulfosuccinate, fatty acid isethionate, fatty acid sarcosinate, fatty acid tauride, fatty acid glutamate, ⁇ Olefin sulfonates, ether carboxylic acids, alkyl oligoglucosides, fatty acid glucamides, alkylamide betaines and / or protein fatty acid condensation products.
  • Powders and coloring materials are roughly classified into constitution powders, organic coloring materials, inorganic coloring materials, pearl pigments, surface-treated powders, and composite powders.
  • the body powder include pulverized products of clay minerals typified by mica, talc, synthetic inorganic powder, organic powder, metallic soap, synthetic polymer powder and the like.
  • the organic coloring materials include tar pigments and natural pigments.
  • the inorganic coloring materials include iron oxides, gunjow, carbon black and the like.
  • pearl pigments include mica titanium.
  • animal and plant extracts can also be used as an active ingredient. These are compounds or compositions extracted from animals and plants by any extraction method. The functions mainly include moisturizing action, soft and emollient action, cell activating action, tyrosinase activity inhibiting action and the like, and the term may be changed accordingly.
  • animal and plant extracts include sodium hyaluronate, sodium chondroitin sulfate, chitin, chitosan, collagen, elastin, peptide, lecithin, placenta extract, hematin, bovine spleen extract, placenta extract and the like.
  • Amino acids are carboxylic acids having an amino group, but imino acids such as proline and hydroxyproline are also included therein. Examples include glycine, alanine, valine, isoleucine, arginine, water soluble collagen, casein and the like.
  • vitamins control the nutrition of animals and plants in trace amounts, and collectively refer to a group of organic compounds that act catalytically to facilitate physiological functions such as reproduction and metabolism. It is Examples include vitamins A, B1, B2, B5, B6, B12, C, D2, D3, E, K1, K2, K3, biotin, nicotinic acid, folic acid and the like.
  • Stericidal and preservative Sterilizers and preservatives can be used to prevent microbial contamination of the ultraviolet absorbing composition and to maintain product quality and safety.
  • the bactericide can also be incorporated into cosmetics used to kill or reduce bacteria growing on the skin.
  • examples of bactericidal and antiseptic agents include benzoic acid, salicylic acid, sorbic acid, parahydroxybenzoic acid ester, benzalkonium chloride, benzethonium chloride, halocarbane, 2,4,4-trichloro-2-hydroxyphenol and the like.
  • microbicide and preservative used for suppression of scalp bacteria considered to be a cause of dandruff trichlorocarbanilide, zinc pyrithione, hinokitiol, phenol and the like can be mentioned.
  • Antioxidant Cosmetics contain oils and fats, waxes, fatty acids, esters, surfactants, perfumes, and various active ingredients. These raw materials absorb oxygen in the air and gradually undergo autoxidation to deteriorate , It exhibits the phenomenon of so-called acid loss. Acid loss causes unpleasant odor and discoloration, and not only impairs the stability of the product, but also peroxides produced by acid loss are representative skin irritant substances and adversely affect the human body. Substances that prevent oxidation or delay the onset of oxidation by the addition are called antioxidants or antioxidants.
  • antioxidants include amino acids (eg, glycine, histidine, tyrosine, tryptophan) and derivatives thereof, imidazoles (eg, urocanic acid) and derivatives thereof, peptides such as D, L-carnosine, D-carnosine, L-carnosine And their derivatives (eg, anserine), carotenoids, carotenes (eg, ⁇ -carotene, lycopene) and their derivatives, chlorogenic acid and its derivatives, lipoic acid and its derivatives (eg, dihydrolipoic acid), aurothioglucose, propyl Thiouracil, and other thiols (eg, thiorhodoxin, glutathione, cysteine, cystine, cystamine, and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl Palmitoyl, oleyl, thi
  • (metal) chelating agents eg, ⁇ -hydroxy fatty acid, palmitic acid, phytic acid, lactoferrin
  • ⁇ -hydroxy acids eg, citric acid, lactic acid, malic acid
  • humic acid bile acid, bile extract, Bilirubin, biliverdin, EDTA and its derivatives
  • unsaturated fatty acids and their derivatives eg ⁇ -linolenic acid, linoleic acid, oleic acid
  • folic acid and its derivatives ubiquinone and ubiquinol and their derivatives
  • vitamin C and its derivatives eg , Ascorbyl palmitate, ascorbyl phosphate Mg, ascorbyl acetate, tocopherols and derivatives (eg, vitamin E acetate, tocotrienol), vitamin A and derivatives (vitamin A palmitate), and coniferyl benzoe of benzoin resin , Rutinic acid and its derivatives, ⁇
  • Sequestering agent Metal ions promote oxidation of cosmetic raw materials, which may cause odors or discoloration, or may cause the quality of cosmetic products to deteriorate, such as causing turbidity or precipitation in transparent cosmetic products.
  • the action of the drug may be inhibited, or the drug and the compound may be made to develop a color.
  • Sequestering agents may be used to prevent these. Examples of the sequestering agent include edetate, sodium polyphosphate, sodium citrate, gluconic acid, tartaric acid and the like, and they contain an acid group having a salt forming ability or an atomic group having a coordination ability.
  • perfume oils for imparting a scent to UV-absorbing compositions mention may be made of perfume oil mixtures of natural and / or synthetic aromatic substances. Natural aromatic substances are, for example, extracts from flowers (lily, lavender, rose, jasmine, nerol, ylang ylang), extracts from stems and leaves (geranium, patchouli, petit glen), extracts from fruits (anisede) , Coriander, caraway, sandalwood extract, extract from berry skin (bergamot, lemon, orange), extract from root (maes, angelica, celery, cardamom, costa (costus), iris (iris), carmus ( (calmus)), extracts from trees (pinewood, sandalwood, guaiacwood, cedarwood, rosewood), extracts from herbs and grass (tarragon, lemongrass, sage, thyme), extracts from needles and branches (Tsuga, pine, Scott and Yamamatsu (mountain pi ne)), resins
  • aromatic compounds of ester type include benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethylbenzylcarbinyl acetate, phenylethyl acetate, linalyl benzoate, benzyl formate, ethyl methyl Phenyl glycinate, allyl cyclohexyl propionate, stilallyl propionate and benzyl salicylate.
  • ether for example, benzyl ethyl ether
  • aldehyde for example, a linear alkanol having 8 to 18 hydrocarbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamenaldehyde, hydroxycitronellal, lilliard And bourgeonal; ketones such as ionones, isomethylionone and methyl cedryl ketones; alcohols such as anethole, citronellol, eugenol, isoeugenol, geraniol, linalool, phenyl Ethyl alcohol and terpinol are mentioned; hydrocarbons mainly include terpenes and balsams.
  • Fragrances usually use a mixture of several aromatic substances in order to create an attractive scent and to sustain the incense effect.
  • Relatively low volatility ethereal oils mainly used as aroma components are also suitable as flavoring oils, for example sage oil, chamomile oil, clove oil, melissa oil, cinnamon leaf oil, lime blossom oil, Juniper berry oil, vetiver oil, olibanum oil, galvanum oil, labolanum oil and labangine oil.
  • antifoam agents such as silicone
  • structurants such as maleic acid
  • solubilizers such as ethylene glycol, propylene glycol, glycerin or diethylene glycol
  • opacifiers such as latex Styrene / PVP or styrene / acrylamide copolymers
  • complexing agents such as EDTA, NTA, alanine diacetic acid or phosphonic acids
  • propellants such as propane / butane mixtures, N 2 O, dimethyl ether, CO 2 , N 2 or air
  • a skin roughening agent, an antiaging agent, a skin-whitening agent, a hair restorer etc. may further be included as an active ingredient.
  • Anti-dandruff agent As the antidandruff agents, climbazole, octopirox, zinc pyrithione and the like mentioned above in the section of the microbicide can be used.
  • Film forming agent As film forming agents that can be used in the present invention, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinyl pyrrolidone, vinyl pyrrolidone / vinyl acetate copolymer, acrylic acid, collagen, hyaluronic acid and their salts in a high ratio And polymers of quaternary cellulose derivatives, and similar compounds.
  • hydrotropes to improve the flow behavior, for example, ethoxylated or non-ethoxylated mono-alcohols with a low number of carbon atoms, diols or polyols or their ethers (eg ethanol , Isopropanol, 1,2-dipropanediol, propylene glycol, glycerin, ethylene glycol, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, diethylene glycol monomethyl ether; Diethylene glycol monoethyl ether, diethylene glycol monobutyl ether and similar products).
  • ethers eglycerin, ethylene glycol, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethy
  • the polyol used for this purpose is preferably a compound having 2 to 15 carbon atoms and at least two hydroxy groups.
  • the polyols may also contain further functional groups, in particular amino groups, and / or be modified with nitrogen.
  • Typical examples are: glycerol, alkylene glycols such as ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol, and also polyethylene glycol having an average molecular weight of 100 to 1000 daltons;
  • methylol compounds such as, in particular, trimethylolethane, trimethylolpropane, trimethylol Butane, pentaerythritol and dipentaerythritol; lower alkyl-glucosides, in particular those having 1 to 8 carbon atoms in the
  • an aqueous composition such as a lotion in a cosmetic is a low viscosity composition using ion-exchanged water, purified water and the like as main components and optionally using a water-soluble alcohol and the like, and it is water-soluble in the water phase.
  • a water dispersible moisturizing agent or buffer may be added, the moisturizing agent or the flavor may be added to the alcohol phase, and then the aqueous phase may be obtained by mixing with the alcohol layer.
  • the ultraviolet absorbing compound is preferably added to the alcohol layer, and when metal oxide particles and the like are used as the other ultraviolet absorbing compound, it can be redispersed by shaking at the time of use.
  • the emulsion composition can take the form of a relatively low viscosity milky (lotion like) composition and a high viscosity creamy composition.
  • the emulsification state may be an oil-in-water (O / W) type or a water-in oil (W / O) type.
  • the emulsion composition prepares an aqueous phase containing water and a moisturizing component and an oil phase containing an oil component and an oil-soluble active ingredient in advance, and usually shears while heating due to the function of a surfactant contained in the oil phase. It is obtained by applying a force.
  • Medicinal active ingredients and UV absorbers are usually incorporated into the oil phase.
  • oil phase ratio In the case of an emulsion (lotion) composition, those having an oil phase ratio of about 3 to 30% by mass, 10 to 50% by mass, etc. are mentioned, and in the case of a cream, the oil phase ratio is Those having 30 to 50% by mass and those having 50 to 85% by mass can be mentioned.
  • Gel-like composition Moreover, it can be taken as an aspect of a gel-like composition containing any of an aqueous phase component and an oil phase component as a main component.
  • An aqueous gel is formed by using the gelling ability of a water-soluble polymer, and can contain an oil component in a small amount.
  • Solid composition The solid composition which shape
  • a so-called powdery type containing 80 to 95% by mass of powder such as pigment and 5 to 20% by mass of oil
  • an oil-based stick type containing 35 to 60% by mass of powder and 40 to 65% by mass of oil It can take a form.
  • the UV absorbing composition of the present invention can take the form of the various dosage forms described above.
  • the ultraviolet absorbing composition of the present invention to skin and hair, the effects of ultraviolet rays harmful to the skin and hair can be effectively prevented, and the use thereof is wide.
  • the ultraviolet absorbing composition according to the present invention is an ultraviolet absorbing composition in the high UV-A region even when it is formed into a thin film, so that the object of the present invention is intended to suppress the influence of ultraviolet rays.
  • ultraviolet rays can be effectively blocked.
  • the composition may be applied directly to the object, or a transparent substrate coated with an ultraviolet absorbing composition may be applied. For example, by forming a film of the ultraviolet absorbing composition of the present invention using a resin base and coating the target with this sheet, it is possible to effectively block ultraviolet light.
  • the maximum absorption wavelength of a solution in which 0.53 ⁇ 10 ⁇ 5 mol / L of the ultraviolet absorbing compound [the above-mentioned exemplified compound (I-5)] is dissolved in dimethyl sulfoxide is determined by using U- of Hitachi High-Technologies Corp. It was 375 nm as measured using a 4100 spectrophotometer. (Evaluation of the physical properties)
  • the resulting ultraviolet absorbing composition of Example 1 is applied to a 5 ⁇ 7 cm glass substrate so that the thickness after drying is 10 ⁇ m, put into a blower dryer, and dried at 100 ° C. for 90 seconds to obtain a glass substrate Then, a 10 ⁇ m thick film made of an ultraviolet absorbing composition was formed.
  • Table 1 The following physical property evaluations were performed, and the results are shown in Table 1 below.
  • an ultraviolet ray absorbing compound the above exemplified compound (I-6)
  • I-6 ultraviolet ray absorbing compound
  • the maximum absorption wavelength of a solution in which 0.53 ⁇ 10 ⁇ 5 mol / L of the ultraviolet absorbing compound [the above-mentioned exemplified compound (I-6)] was dissolved in dimethyl sulfoxide was measured in the same manner as in Example 1. By the way, it was 375 nm.
  • the resulting ultraviolet absorbing composition of Example 1 is applied to a 5 ⁇ 7 cm glass substrate so that the thickness after drying is 10 ⁇ m, put into a blower dryer, and dried at 100 ° C. for 90 seconds to obtain a glass substrate Then, a 10 ⁇ m thick film made of an ultraviolet absorbing composition was formed.
  • the following physical property evaluations were performed, and the results are shown in Table 1 below.
  • Content relative to ultraviolet ray absorbing composition 1.5 ⁇ 10 ⁇ 4 mol / g] and the mixture was stirred for 30 minutes to be completely dissolved to prepare an ultraviolet ray absorbing composition.
  • the maximum absorption wavelength of the solution in which 1.5 ⁇ 10 ⁇ 5 mol / L of the ultraviolet absorbing compound [exemplified compound (I-2) described in JP 2008-81445] is dissolved in ethyl acetate is carried out.
  • the resulting ultraviolet absorbing composition of Example 1 is applied to a 5 ⁇ 7 cm glass substrate so that the thickness after drying is 10 ⁇ m, put into a blower dryer, and dried at 100 ° C. for 90 seconds to obtain a glass substrate Then, a 10 ⁇ m thick film made of an ultraviolet absorbing composition was formed.
  • Table 1 The following physical property evaluations were performed, and the results are shown in Table 1 below.
  • ⁇ Light transmittance test> The light transmittance of the 10 ⁇ m film obtained above was evaluated. The absorbance was measured for absorption spectra at 390 nm, 420 nm and 440 nm using a U-4100 spectrophotometer manufactured by Hitachi High-Technologies Corp. to determine the light transmittance. Evaluation was performed based on the following evaluation criteria. (Beam transmission at a wavelength of 390 nm) A: The light transmittance at 390 nm is 5% or less B: The light transmittance at 390 nm is more than 5% and 10% or less C: The light transmittance at 390 nm is more than 10%
  • Light transmission at wavelengths 420 nm and 440 nm A: 80% or more of transmittance at 440 nm, and 70% or more of transmittance at 420 nm C: less than 80% of transmittance at 440 nm, and less than 70% of transmittance at 420 nm
  • solubility test> The solubility was based on the following evaluation criteria by visually observing whether or not the compound was dissolved at the preparation temperature when the compound was dissolved in the base at the time of preparation of the ultraviolet absorbing composition in Examples and Comparative Examples. The evaluation was done. A: easily dissolved B; although it was dissolved, it took time.
  • the ultraviolet ray absorbing compositions of Examples 1 to 3 are excellent in ultraviolet ray absorptivity in the UV-A region and good in visible light transmittance.
  • the ultraviolet absorptivity in the UV-A region was insufficient.
  • the quantity of a ultraviolet absorption compound is increased from 0.096g to 0.54g so that the light transmittance in wavelength 390nm may be 5% or less, and an ultraviolet absorption composition is prepared.
  • Example 4 Preparation of sunscreen cream According to the formulation shown in Table 2 below, the phases (I) and (II) are respectively heated to 70 to 80 ° C. and uniformly dissolved. Thereafter, phase (I) is added to phase (II), and the mixture is stirred at 5,000 rpm for 7 minutes with a homomixer while maintaining at 80 ° C. Further, the mixture was cooled with paddle stirring, stopped stirring at 35 to 30 ° C., and allowed to stand to obtain a sunscreen cream.
  • NIKKOL nicomrus 41 described in Table 2 below is an emulsifier manufactured by Nikko Chemicals.
  • Example 5 Preparation of sunscreen cream According to the formulation shown in Table 3 below, a mixture is prepared by stirring the phase (I) with a homomixer at 6,000 rpm for 10 minutes while prewarming to 80 ° C. The phases (II) and (III) are heated to 80 ° C., respectively. First, the warmed (II) phase component is added to the (I) phase, stirred, and uniformly mixed, and then the (III) phase component is gradually added while stirring and emulsified, and maintained at 80 ° C. While stirring, 5,000 rpm for 7 minutes with a homomixer. Thereafter, the mixture was cooled with paddle stirring, stopped stirring at 35 to 30 ° C., and allowed to stand to obtain a sunscreen cream.
  • the ultraviolet absorbing composition (Sunscreen cream) of Examples 4 and 5 obtained above is applied to a transparent substrate similar to that used in the evaluation of physical properties in Example 1 to form a 10 ⁇ m film, The absorbance was measured using a Hitachi High-Technologies Corporation U-4100 spectrophotometer to determine the light transmittance at a wavelength of 390 nm. As a result, as in Examples 1 to 3, as a result, the light transmittance was 5% or less in all cases, and the ultraviolet absorption effect in the effective UV-A region was shown. When these sunscreen creams were used by hand, they were well familiar with the skin and could be easily stretched thinly.

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Abstract

L’invention concerne une composition absorbant les ultraviolets, qui contient de 1,0 × 10-7 mol/g à 1,0 × 10-3 mol/g d’un composé absorbant les ultraviolets qui a une longueur d’onde d’absorption maximale de 380 nm ou moins dans une solution préparée en dissolvant le composé dans un solvant qui n’a pas d’absorption maximale dans la plage de longueurs d’onde allant de 300 à 600 nm, de manière à ce que la concentration soit de 1,0 × 10-6 mol/L à 1,0 × 10-3 mol/L à 25 °C. Lorsque la composition est mise sous la forme d’un film d’une épaisseur de 10 µm, le film a un taux de transmission de 5 % ou moins pour la lumière d’une longueur d’onde de 390 nm.
PCT/JP2009/068281 2008-11-10 2009-10-23 Composition absorbant les ultraviolets, formulations cosmétiques et pharmaceutiques l’utilisant et procédé de blocage des ultraviolets WO2010053017A1 (fr)

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Citations (8)

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Publication number Priority date Publication date Assignee Title
JPS6481858A (en) * 1987-06-30 1989-03-28 Eastman Kodak Co Polymethine dye or ultraviolet abosrber
JP2000328039A (ja) * 1999-05-19 2000-11-28 Hayashibara Biochem Lab Inc 光吸収剤
JP2005538072A (ja) * 2002-07-10 2005-12-15 チバ　スペシャルティ　ケミカルズ　ホールディング　インコーポレーテッド 化粧品用途のためのメロシアニン誘導体
WO2006125676A1 (fr) * 2005-05-27 2006-11-30 L'oreal Photostabilisation de derive dibenzoylmethane par derive merocyanine-sulfone et compositions cosmetiques photoprotectrices en contenant
JP2007514709A (ja) * 2003-12-17 2007-06-07 チバ　スペシャルティ　ケミカルズ　ホールディング　インコーポレーテッド 化粧品用メロシアニン誘導体
WO2007071582A1 (fr) * 2005-12-20 2007-06-28 Ciba Holding Inc. Dérivés de mérocyanine
JP2008504343A (ja) * 2004-06-29 2008-02-14 チバ　スペシャルティ　ケミカルズ　ホールディング　インコーポレーテッド メロシアニン誘導体
JP2008513419A (ja) * 2004-09-20 2008-05-01 ロレアル シランメロシアニンスルホン誘導体；シランメロシアニンスルホン誘導体を含有する光保護用組成物；それらのｕｖフィルターとしての使用

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6481858A (en) * 1987-06-30 1989-03-28 Eastman Kodak Co Polymethine dye or ultraviolet abosrber
JP2000328039A (ja) * 1999-05-19 2000-11-28 Hayashibara Biochem Lab Inc 光吸収剤
JP2005538072A (ja) * 2002-07-10 2005-12-15 チバ　スペシャルティ　ケミカルズ　ホールディング　インコーポレーテッド 化粧品用途のためのメロシアニン誘導体
JP2007514709A (ja) * 2003-12-17 2007-06-07 チバ　スペシャルティ　ケミカルズ　ホールディング　インコーポレーテッド 化粧品用メロシアニン誘導体
JP2008504343A (ja) * 2004-06-29 2008-02-14 チバ　スペシャルティ　ケミカルズ　ホールディング　インコーポレーテッド メロシアニン誘導体
JP2008513419A (ja) * 2004-09-20 2008-05-01 ロレアル シランメロシアニンスルホン誘導体；シランメロシアニンスルホン誘導体を含有する光保護用組成物；それらのｕｖフィルターとしての使用
WO2006125676A1 (fr) * 2005-05-27 2006-11-30 L'oreal Photostabilisation de derive dibenzoylmethane par derive merocyanine-sulfone et compositions cosmetiques photoprotectrices en contenant
WO2007071582A1 (fr) * 2005-12-20 2007-06-28 Ciba Holding Inc. Dérivés de mérocyanine

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