WO1995004519A1 - Poorly water-soluble salts of sunscreen agents - Google Patents
Poorly water-soluble salts of sunscreen agents Download PDFInfo
- Publication number
- WO1995004519A1 WO1995004519A1 PCT/EP1994/002668 EP9402668W WO9504519A1 WO 1995004519 A1 WO1995004519 A1 WO 1995004519A1 EP 9402668 W EP9402668 W EP 9402668W WO 9504519 A1 WO9504519 A1 WO 9504519A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- salt
- sulphonate
- metal cation
- cinnamate
- aluminium
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 30
- 239000000516 sunscreening agent Substances 0.000 title claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 230000000475 sunscreen effect Effects 0.000 claims abstract description 16
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 13
- 229910052751 metal Inorganic materials 0.000 claims abstract description 13
- 239000002184 metal Substances 0.000 claims abstract description 13
- 239000004411 aluminium Substances 0.000 claims abstract description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 11
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000001768 cations Chemical class 0.000 claims abstract description 9
- 239000011701 zinc Substances 0.000 claims abstract description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 8
- 150000002891 organic anions Chemical class 0.000 claims abstract description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052742 iron Inorganic materials 0.000 claims abstract description 4
- 229910052746 lanthanum Inorganic materials 0.000 claims abstract description 4
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052718 tin Inorganic materials 0.000 claims abstract description 4
- 239000011135 tin Substances 0.000 claims abstract description 4
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 4
- 239000010936 titanium Substances 0.000 claims abstract description 4
- 230000005855 radiation Effects 0.000 claims description 8
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 7
- AFDXODALSZRGIH-QPJJXVBHSA-N (E)-3-(4-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C=C1 AFDXODALSZRGIH-QPJJXVBHSA-N 0.000 claims description 6
- 229940114081 cinnamate Drugs 0.000 claims description 4
- XDMOQOJRODHAPO-UHFFFAOYSA-N 2-hydroxybenzoic acid;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C1=CC=CC=C1O XDMOQOJRODHAPO-UHFFFAOYSA-N 0.000 claims description 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
- ZJQCPLWCDJJLRO-UHFFFAOYSA-N 4-aminobenzoic acid;2-hydroxybenzoic acid;3-(4-methoxyphenyl)prop-2-enoic acid;3-phenylprop-2-enoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1.OC(=O)C1=CC=CC=C1O.OC(=O)C=CC1=CC=CC=C1.COC1=CC=C(C=CC(O)=O)C=C1 ZJQCPLWCDJJLRO-UHFFFAOYSA-N 0.000 claims description 2
- PCCSGXBUYUQIBS-UHFFFAOYSA-N amino 3h-benzimidazole-5-sulfonate Chemical compound NOS(=O)(=O)C1=CC=C2N=CNC2=C1 PCCSGXBUYUQIBS-UHFFFAOYSA-N 0.000 claims description 2
- 229940064734 aminobenzoate Drugs 0.000 claims description 2
- FMJSMJQBSVNSBF-UHFFFAOYSA-N octocrylene Chemical compound C=1C=CC=CC=1C(=C(C#N)C(=O)OCC(CC)CCCC)C1=CC=CC=C1 FMJSMJQBSVNSBF-UHFFFAOYSA-N 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 abstract description 21
- 150000007524 organic acids Chemical class 0.000 abstract description 3
- 235000005985 organic acids Nutrition 0.000 abstract description 3
- 238000002835 absorbance Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- 150000001450 anions Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 210000003491 skin Anatomy 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000003981 vehicle Substances 0.000 description 6
- 230000008033 biological extinction Effects 0.000 description 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- -1 cinnamate Chemical class 0.000 description 2
- 210000004207 dermis Anatomy 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 230000000258 photobiological effect Effects 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- 150000003873 salicylate salts Chemical class 0.000 description 2
- 229960004025 sodium salicylate Drugs 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- JKXYOQDLERSFPT-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-octadecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO JKXYOQDLERSFPT-UHFFFAOYSA-N 0.000 description 1
- KKJKXQYVUVWWJP-UHFFFAOYSA-N 4-[(4,7,7-trimethyl-3-oxo-2-bicyclo[2.2.1]heptanylidene)methyl]benzenesulfonic acid Chemical compound CC1(C)C2CCC1(C)C(=O)C2=CC1=CC=C(S(O)(=O)=O)C=C1 KKJKXQYVUVWWJP-UHFFFAOYSA-N 0.000 description 1
- KERMUFCCTOREID-UHFFFAOYSA-N 5-methyl-2-[(4,7,7-trimethyl-3-oxo-2-bicyclo[2.2.1]heptanylidene)methyl]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(C)=CC=C1C=C1C(=O)C2(C)CCC1C2(C)C KERMUFCCTOREID-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- 208000012641 Pigmentation disease Diseases 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- WSDISUOETYTPRL-UHFFFAOYSA-N dmdm hydantoin Chemical compound CC1(C)N(CO)C(=O)N(CO)C1=O WSDISUOETYTPRL-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- AFDXODALSZRGIH-UHFFFAOYSA-N p-coumaric acid methyl ether Natural products COC1=CC=C(C=CC(O)=O)C=C1 AFDXODALSZRGIH-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000013074 reference sample Substances 0.000 description 1
- 238000000985 reflectance spectrum Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- DXIHILNWDOYYCH-UHDJGPCESA-M sodium;(e)-3-phenylprop-2-enoate Chemical compound [Na+].[O-]C(=O)\C=C\C1=CC=CC=C1 DXIHILNWDOYYCH-UHDJGPCESA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/26—Aluminium; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/27—Zinc; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/60—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in meta- or para- positions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/41—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by carboxyl groups, other than cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/44—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing doubly-bound oxygen atoms bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2224—Compounds having one or more tin-oxygen linkages
Definitions
- This invention relates to sunscreen agents, that is to say compounds capable of absorbing ultra violet radiation with a wavelength in the range from 290 to 400 nanometres.
- the invention also relates to sunscreen compositions for application to human skin incorporating the sunscreen agents.
- UV ultra-violet
- UV-A rays (320-400nm wavelength) which penetrate deeper into the skin (to the dermis and beyond) .
- Sunscreen compositions should desirably provide protection against both UV-A and UV-B rays, but protection against UV- A rays is particularly desirable, in order to prevent the long term photobiological effects resulting from UV-A radiation.
- sunscreen agents are soluble salts of organic acids such as cinnamate, which incorporate an aromatic nucleus or other conjugates system which provides ultraviolet absorption.
- organic acids such as cinnamate, which incorporate an aromatic nucleus or other conjugates system which provides ultraviolet absorption.
- sunscreen agents are soluble salts of organic acids such as cinnamate, which incorporate an aromatic nucleus or other conjugates system which provides ultraviolet absorption.
- this invention provides a sunscreen composition for application to human skin comprising a cosmetically acceptable vehicle incorporating a salt formed between an organic anion which displays ultraviolet absorption over at least a portion of the wavelength range from 290 to 400 nanometres, and a metal cation characterised in that the metal cation is one or a mixture of aluminium, zinc, titanium, tin, iron or lanthanum and the salt has a solubility of less than 2g/litre in water at 20°C.
- the water solubility of the salts may possibly be less than lg/litre.
- EP-A-557089 there are disclosed insoluble macromolecular salts which are layered double hydroxides in which metal ions are linked through hydroxy groups.
- This invention is particularly concerned with poorly soluble salts which are other than these layered double hydroxides of the formula
- N is one or a mixture of trivalent metal ions
- M is one or a mixture of divalent metal ions or is lithium
- the poorly soluble salts of this invention will frequently be simple salts of a single metal cation so that individual crystals will contain only a single metal. Mixtures of such salts could be used, so that more than one metal is present, but in different crystals.
- the salts of this invention may possibly be devoid of bridging hydroxy groups connecting metal atoms.
- this invention provides use of poorly soluble salts as defined above as sunscreen agents or to prepare sunscreen compositions.
- a third aspect of the invention is the poorly soluble salts themselves as defined above.
- the ultraviolet absorbing anions have a fairly strong absorption in at least a portion of the stated range from 290 to 400 nanometres.
- This may be specified as a requirement that the acid form or a simple alkali metal or ammonium salt of the anion exhibits absorption with a molar extinction coefficient of at least 2 x 10 3 , preferably 3 x 10 3 , more preferably at least 5 x 10 3 and yet more preferably at least 8 x 10 3 over at least a portion of the stated wavelength range from 290 to 400nm.
- the poorly soluble salts of this invention may themselves have molar extinction coefficients of the magnitudes given in the previous paragraph, but it is easier to measure absorbance in solution and thus may be more convenient to specify the extinction coefficient of a soluble salt.
- Effective ultraviolet absorption may be provided by an absorption band whose maximum is outside the stated range.
- the p-methoxy cinnamate ion has an absorption maximum at 285 nanometres but the absorption band is broad enough to provide strong absorption over a range from 290 nanometres up to at least around 320 nanometres.
- absorption in the range 290 to 400 nanometres will be provided by an absorption band with a maximum in the range 260 to 360 nanometres.
- the anions do not have strong absorption in the visible band from 400 to 700 nanometres, especially in the part of it from 450 nanometres upwards, notably from 450 or 500 to 650 nanometres.
- the extinction coefficient for absorption in such ranges may preferably be no greater than 5 x 10 2 throughout the ranges concerned.
- the molar extinction coefficient of a substance is usually measured in solution and is then given by the formula
- I is the intensity of radiation transmitted through the sample
- Iache is the intensity of radiation transmitted through a reference sample consisting of the same solvent but without the substance under test
- c is molar concentration in moles/litre
- the anions which absorb ultraviolet radiation may suitably be one or more of the following:
- Particularly preferred anions are:
- the poorly soluble salts can readily be prepared by precipitation from an aqueous solution of the corresponding alkali metal or ammonium salt, and then separated by filtration.
- the sunscreen compositions of this invention include a cosmetically acceptable vehicle.
- the poorly soluble salts of this invention can be suspended as a dispersion in the vehicle. Preparation may simply consist of adding the poorly soluble salt to the vehicle, and then mixing to form a suspension.
- the vehicle is aqueous.
- the composition is rubbed onto skin and the water then evaporates, along with any volatile organic compounds included in the vehicle. This leaves the poorly soluble salt as a deposit on the skin.
- the aqueous vehicle may be an oil-in-water emulsion with the poorly soluble salt suspended in that emulsion.
- a sunscreen composition according to this invention will contain from 0.05 to 50% by weight of the poorly soluble salt, more preferably from 0.1 to 30% by weight, yet more preferably 2 to 20% by weight.
- the amount which is incorporated will affect the amount of ultraviolet absorption achieved, of course. Therefore amounts towards the upper end of the range would be used for sunscreen compositions intended to give a high degree of protection against ultraviolet radiation.
- compositions according to this invention may be included in sunscreen compositions according to this invention. It is within the scope of this invention to incorporate an additional sunscreen agent. Possibilities include nonionic organic sunscreen agents, inorganic sunscreen agents such as finely divided titanium dioxide and particles of organic polymers.
- sunscreen composition materials which may possibly be included in a sunscreen composition include thickening agents, emollient oils, humectants and fluids to enhance lubricity, notably silicone oils. Minor constituents which may be present include perfume and preservatives.
- X-ray powder diffraction pattern of the product showed major peaks at 12.1A, 6.1A, 5.2A and 3.9A which are characteristic of this material.
- X-ray powder diffraction pattern of the product showed major peaks at 9.9A, 5.16A, 3.52A, and 3.22A which are characteristic of this material.
- the X-ray diffraction pattern of the product showed major peaks at 19.6A, 9.8A, and 6.5A which are characteristic of this material.
- the UV powder reflectance spectra showed a broad absorption band extending from below 250nm to about 340nm and with a tail extending to about 380nm.
- Heat Phase B to 80°C and homogenise. Heat Phase A to 80°C and then slowly add Phase B while stirring. Add in Phase C and then cool to 40°C and add Phase D.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Inorganic Chemistry (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Cosmetics (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU74990/94A AU7499094A (en) | 1993-08-11 | 1994-08-10 | Poorly water-soluble salts of sunscreen agents |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9316646.0 | 1993-08-11 | ||
| GB939316646A GB9316646D0 (en) | 1993-08-11 | 1993-08-11 | Sunscreen agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1995004519A1 true WO1995004519A1 (en) | 1995-02-16 |
Family
ID=10740294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1994/002668 WO1995004519A1 (en) | 1993-08-11 | 1994-08-10 | Poorly water-soluble salts of sunscreen agents |
Country Status (4)
| Country | Link |
|---|---|
| AU (1) | AU7499094A (enrdf_load_stackoverflow) |
| GB (1) | GB9316646D0 (enrdf_load_stackoverflow) |
| IN (1) | IN181787B (enrdf_load_stackoverflow) |
| WO (1) | WO1995004519A1 (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2762839A1 (fr) * | 1997-04-30 | 1998-11-06 | Oreal | Nouveaux derives de l'acide salicylique et leur utilisation dans une composition cosmetique et/ou dermatologique |
| WO2002095393A3 (en) * | 2001-05-24 | 2003-05-22 | Ca Nat Research Council | Drug evolution: drug design at hot spots |
| CZ302399B6 (cs) * | 2009-12-04 | 2011-04-27 | Výzkumný ústav anorganické chemie, a. s. | Zpusob výroby salicylátu hlinitého |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60174710A (ja) * | 1984-02-20 | 1985-09-09 | Kanebo Ltd | 日焼け止め化粧料 |
| JPS60174711A (ja) * | 1984-02-20 | 1985-09-09 | Kanebo Ltd | 日焼け止め化粧料 |
-
1993
- 1993-08-11 GB GB939316646A patent/GB9316646D0/en active Pending
-
1994
- 1994-08-10 AU AU74990/94A patent/AU7499094A/en not_active Abandoned
- 1994-08-10 WO PCT/EP1994/002668 patent/WO1995004519A1/en active Application Filing
- 1994-08-11 IN IN387BO1994 patent/IN181787B/en unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60174710A (ja) * | 1984-02-20 | 1985-09-09 | Kanebo Ltd | 日焼け止め化粧料 |
| JPS60174711A (ja) * | 1984-02-20 | 1985-09-09 | Kanebo Ltd | 日焼け止め化粧料 |
Non-Patent Citations (1)
| Title |
|---|
| PATENT ABSTRACTS OF JAPAN vol. 10, no. 17 (C - 324) * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2762839A1 (fr) * | 1997-04-30 | 1998-11-06 | Oreal | Nouveaux derives de l'acide salicylique et leur utilisation dans une composition cosmetique et/ou dermatologique |
| US5917088A (en) * | 1997-04-30 | 1999-06-29 | L'oreal | Salicyclic acid derivatives, process of preparation and uses thereof |
| WO2002095393A3 (en) * | 2001-05-24 | 2003-05-22 | Ca Nat Research Council | Drug evolution: drug design at hot spots |
| CZ302399B6 (cs) * | 2009-12-04 | 2011-04-27 | Výzkumný ústav anorganické chemie, a. s. | Zpusob výroby salicylátu hlinitého |
Also Published As
| Publication number | Publication date |
|---|---|
| AU7499094A (en) | 1995-02-28 |
| IN181787B (enrdf_load_stackoverflow) | 1998-09-19 |
| GB9316646D0 (en) | 1993-09-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5573755A (en) | Sunscreen agents | |
| EP0557089B1 (en) | Sunscreen agents containing layered double hydroxides | |
| US8540972B2 (en) | Sunscreen product comprising hydroxyapatite as physical filter | |
| WO2000066076A1 (en) | Sprayable sunscreen compositions | |
| US5474762A (en) | Sunscreen agents | |
| CN104114143B (zh) | 用于防护皮肤对抗uv射线的化妆品套装 | |
| JP3643924B2 (ja) | ベンジリデンショウノウ及び／又はジベンゾイルメタン及び／又はトリアジン及び酒石酸ジアルキルを含有する光保護組成物及びその化粧用途 | |
| CN102946848A (zh) | 含有肉桂酰氨基烷基胺的2-羟基磺基甜菜碱的广谱防晒组合物 | |
| FI98885C (fi) | Aurinkosuojakoostumuksia | |
| WO1993010753A1 (en) | Uva-absorbing sunscreen metal complexes | |
| WO1993011095A1 (en) | Uva-absorbing sunscreen metal complexes | |
| EP1860070A1 (en) | A particle comprising a host lattice and a guest, its preparation and use in ultraviolet light screening compositions | |
| JP2023546290A (ja) | キサントマチンを抗酸化剤およびｕｖフィルター安定化剤として含有する光防御化粧品組成物 | |
| WO1994007460A1 (en) | Methods for improving uv absorbance of sunscreen compounds | |
| WO1995004519A1 (en) | Poorly water-soluble salts of sunscreen agents | |
| KR101122743B1 (ko) | 페놀릭산 자외선 흡수제 및 층상형 금속 수산화물의 혼성체, 그 제조방법, 및 그 혼성체를 포함하는 자외선 차단용 조성물 | |
| Levy | UV filters | |
| US20070086962A1 (en) | Stable sunscreen composition | |
| KR102722050B1 (ko) | 선스크린 조성물 | |
| JPH0578334A (ja) | ｐ−アミノ桂皮酸置換トリアジン | |
| US12343424B2 (en) | Photochemically stable, non-leaching, bridged polysilsesquioxane based sunscreens | |
| JP2000212054A (ja) | 複合化粉末を含む組成物 | |
| US20180333347A1 (en) | Photochemically stable, non-leaching sunscreens from epoxide-based silane coupling agents and uv absorbing chromophores | |
| KR101238379B1 (ko) | 자외선흡수제가 포집된 이산화티타늄 캡슐 및 이를 함유하는 화장료 조성물 | |
| WO2025146351A1 (en) | Cosmetic composition comprising bis-ethylhexyloxyphenol methoxyphenyl triazine |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AK | Designated states |
Kind code of ref document: A1 Designated state(s): AM AT AU BB BG BR BY CA CH CN CZ DE DK ES FI GB GE HU JP KE KG KP KR KZ LK LT LU LV MD MG MN MW NL NO NZ PL PT RO RU SD SE SI SK TJ TT UA UZ VN |
|
| AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): KE MW SD AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR NE SN TD TG |
|
| DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
| REG | Reference to national code |
Ref country code: DE Ref legal event code: 8642 |
|
| 122 | Ep: pct application non-entry in european phase | ||
| NENP | Non-entry into the national phase |
Ref country code: CA |