ES2584204T3 - Derivados de hidroxibenzofenona - Google Patents
Derivados de hidroxibenzofenona Download PDFInfo
- Publication number
- ES2584204T3 ES2584204T3 ES07726317.6T ES07726317T ES2584204T3 ES 2584204 T3 ES2584204 T3 ES 2584204T3 ES 07726317 T ES07726317 T ES 07726317T ES 2584204 T3 ES2584204 T3 ES 2584204T3
- Authority
- ES
- Spain
- Prior art keywords
- formula
- dimethicone
- alkylene
- alkyl
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 abstract 1
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229940008099 dimethicone Drugs 0.000 description 6
- 239000004205 dimethyl polysiloxane Substances 0.000 description 6
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 6
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 6
- 229920001296 polysiloxane Polymers 0.000 description 6
- 238000009472 formulation Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 1
- UIVPNOBLHXUKDX-UHFFFAOYSA-N 3,5,5-trimethylhexyl 3,5,5-trimethylhexanoate Chemical compound CC(C)(C)CC(C)CCOC(=O)CC(C)CC(C)(C)C UIVPNOBLHXUKDX-UHFFFAOYSA-N 0.000 description 1
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 description 1
- 230000006750 UV protection Effects 0.000 description 1
- XVAMCHGMPYWHNL-UHFFFAOYSA-N bemotrizinol Chemical compound OC1=CC(OCC(CC)CCCC)=CC=C1C1=NC(C=2C=CC(OC)=CC=2)=NC(C=2C(=CC(OCC(CC)CCCC)=CC=2)O)=N1 XVAMCHGMPYWHNL-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940085262 cetyl dimethicone Drugs 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229940086555 cyclomethicone Drugs 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 229940100554 isononyl isononanoate Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229960001679 octinoxate Drugs 0.000 description 1
- FMJSMJQBSVNSBF-UHFFFAOYSA-N octocrylene Chemical group C=1C=CC=CC=1C(=C(C#N)C(=O)OCC(CC)CCCC)C1=CC=CC=C1 FMJSMJQBSVNSBF-UHFFFAOYSA-N 0.000 description 1
- 229960000601 octocrylene Drugs 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- 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
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- 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
- A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
- A61K8/585—Organosilicon compounds
-
- 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
-
- 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
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
-
- 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
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- 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
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Compuestos de la fórmula (1)**Fórmula** en la que R1 y R2 independientemente el uno del otro son hidrógeno; alquilo C1-C20; alquenilo C2-C20; cicloalquilo C3-C20; cicloalquenilo C3-C10; o R1 y R2 junto con el átomo de nitrógeno que los une forman un anillo heterocíclico de 5- 6 miembros; R3, R4 y R5 independientemente el uno del otro son hidrógeno alquilo C1-C4; alcoxi C1-C4; o un radical de la fórmula a radical of formula (1 a)**Fórmula** R6 es alquilo C1-C6; A es alquileno C3-C6; o (alquileno C1-C5)-O-(CO)- alquileno (C1-C5); y m es 0.
Description
y 5 gotas de un catalizador Karstedt (Aldrich) son disueltos en 10 ml 1-butanol y se añadieron gota a gota durante 30 min.
5 La solución es agitada a 80°C por 8 h. Después de la concentración, el producto en bruto es purificado través de cromatografía de columna para obtener el compuesto de la fórmula (103).
λmax = 357 nm ; E 1/1 = 606
Se preparan seis formulaciones de tipo de silicona de agua. Todas las formulaciones muestran alta eficiencia y una extraordinaria sensación de suavidad en la piel.
Los Ejemplos B1 a B3 son formulaciones de silicona de agua en las que el compuesto de la fórmula (102) es usado como un filtro UV-A de silicona soluble.
15 Ejemplos B4 a B6 son formulaciones de silicona de agua en las que el compuesto de la fórmula (103) es usado como un filtro UV-A de silicona soluble.
Los valores altos de FPS y protección de alta UVA se obtienen como se muestra en la Tabla B1.
- Tabla B1: formulaciones de silicona de agua
- Nombre INCI/Nombre Químico
- % p/p (como se suministra)
- Parte A
- Cetil PEG/PPG-10/1 Dimeticona Ex. B1 Ex. B2 Ex. B3 Ex. B4 Ex. B5 Ex. B6
- Isononil Isononanoato
- 2.80 2.80 2.80 2.80 2.80 2.80
- Cetil dimeticona
- 4.00 4.00 4.00 4.00 4.00 4.00
- Silica Dimetil Sililato
- 1.00 1.00 1.00 1.00 1.00 1.00
- Etilhexil metoxicinamato
- 0.30 0.30 0.30 0.30 0.30 0.30
- Octocrileno
- 6.00 6.00 8.00 6.00 6.00 8.00
- Compuesto de la fórmula (102) preparado de acuerdo con el Ejemplo A2
- 3.00 3.00 300
- Compuesto de la fórmula (103) preparado de acuerdo con el Ejemplo A3
- 3.00 3.50 3.50
- Bis-Etilhexiloxifenol metoxifenil Triazina
- 3.00 3.50 3.50 3.00 3.50 3.50
- Parte B
- Ciclometicona 1.00 1.50 1.00 1.50
- Dimeticona
- 12.00 12.00 12.00 12.00 12.00 12.00
- Dimeticona (y) polímero cruzado de dimeticona/vinil dimeticona
- 5.00 5.00 5.00 5.00 5.00 5.00
9
- Parte C
- Dióxido de titanio (y) hidróxido de aluminio (y) copolímero de Dimeticona/-Meticona (y) sílica hidratada 1.00 1.00 1.00 1.00 1.00 1.00
- Parte D
- Agua 1.50 1.50
- Butilen Glicol
- qs a 100 qs a 100 qs a 100 qs a 100 qs a 100 qs a 100
- Cloruro de sodio
- 3.00 3.00 3.00 3.00 3.00 3.00
- Parte E
- Alcohol 1.00 1.00 1.00 1.00 1.00 1.00
- 5.00
- 5.00
- 5.00
- 5.00
- 5.00
- 5.00
- Resultados:
- Medición SPF In-vitro
- 15 19 30
- Balance de UVA (de acuerdo con DIN 67502)
- 21 26 20
10
Claims (1)
-
imagen1 imagen2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06101454 | 2006-02-09 | ||
| EP06101454 | 2006-02-09 | ||
| PCT/EP2007/051117 WO2007090832A1 (en) | 2006-02-09 | 2007-02-06 | Hydroxybenzophenone derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2584204T3 true ES2584204T3 (es) | 2016-09-26 |
Family
ID=36010871
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES07726317.6T Active ES2584204T3 (es) | 2006-02-09 | 2007-02-06 | Derivados de hidroxibenzofenona |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7999128B2 (es) |
| EP (1) | EP1981895B1 (es) |
| JP (1) | JP5294877B2 (es) |
| ES (1) | ES2584204T3 (es) |
| GB (1) | GB2435041A (es) |
| WO (1) | WO2007090832A1 (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102007024343A1 (de) * | 2007-05-22 | 2008-11-27 | Beiersdorf Ag | Kosmetische Zubereitung mit polymerem UV-Filter und Metalloxiden |
| AR100211A1 (es) * | 2014-05-19 | 2016-09-21 | Interquim Sa | Procedimiento para la preparación de un polímero fotoprotector progresivo de organosilicio; polímero fotoprotector progresivo de organosilicio, su uso, composición que lo comprende, monómero precursor, procedimientos para la preparación de dicho monómero precursor |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2938047A (en) | 1958-11-13 | 1960-05-24 | Union Carbide Corp | Carbobenzophenoneoxyalkyl siloxanes and their preparation |
| US4042613A (en) | 1974-04-23 | 1977-08-16 | Dai Nippon Printing Co., Ltd. | Benzophenone derivatives and their preparation and application |
| US4495360A (en) | 1982-04-30 | 1985-01-22 | General Electric Company | Ultraviolet light absorbing agents, method for making, compositions and articles containing same |
| US5270426A (en) * | 1990-01-22 | 1993-12-14 | Shin-Etsu Chemical Co., Ltd. | Organosilicon compound |
| JPH03287588A (ja) * | 1990-04-02 | 1991-12-18 | Shiseido Co Ltd | ベンゾフェノン誘導体、紫外線吸収剤及び皮膚外用剤 |
| FR2684551B1 (fr) | 1991-12-05 | 1995-04-21 | Oreal | Huile cosmetique filtrante contenant une silicone filtre et un melange d'une silicone volatile et d'une huile de silicone ou d'une gomme de silicone et emulsion cosmetique filtrante contenant une telle huile. |
| EP0667379B1 (de) | 1994-02-10 | 2002-07-17 | Ciba SC Holding AG | Holzschutzanstrich |
| US6071052A (en) | 1997-06-30 | 2000-06-06 | Lok-Mor, Inc. | Extended height lock nut |
| FR2782516B1 (fr) * | 1998-08-21 | 2001-09-07 | Oreal | Procede de photostabilisation de filtres solaires derives du dibenzoylmethane, compositions cosmetiques filtrantes photostabilisees ainsi obtenues et leurs utilisation |
| DE19917906A1 (de) * | 1999-04-20 | 2000-10-26 | Basf Ag | Verwendung von aminosubstituierten Hydroxybenzophenonen als photostabile UV-Filter in kosmetischen und pharmazeutischen Zubereitungen |
| DE10011317A1 (de) | 2000-03-10 | 2001-09-13 | Basf Ag | Verwendung von aminosubstituierten Hydroxybenzophenonen als Lichtschutzmittel und Stabilisatoren für nicht lenbendes organisches Material |
| DE10012408A1 (de) | 2000-03-15 | 2001-09-20 | Basf Ag | Verwendung von Lichtschutzmittelkombinationen, die als wesentlichen Bestandteil aminosubstituierte Hydroxybenzophenone enthalten als photostabile UV-Filter in kosmetischen und pharmazeutischen Zubereitungen |
| DE10143963A1 (de) | 2001-09-07 | 2003-03-27 | Basf Ag | Kosmetische und dermatologische Zubereitungen in Form von W/O-Emulsionen, enthaltend ein aminosubstituiertes Hydroxybenzophenon |
| DE10155963A1 (de) | 2001-11-09 | 2003-05-22 | Beiersdorf Ag | Kosmetische und dermatologische Lichtschutzformulierungen mit einem Gehalt an Hydroxybenzophenonen, Triazin- und/oder Benzotriazol-Derivaten |
| DE60331637D1 (de) * | 2002-04-12 | 2010-04-22 | Dsm Ip Assets Bv | Organosilikon-derivate von amino-hydroxybenzophenonen und ihre verwendung als uv-a-filter in kosmetischen zubereitungen |
| JP4566907B2 (ja) | 2002-12-12 | 2010-10-20 | チバ ホールディング インコーポレーテッド | アミノ置換ヒドロキシフェニルベンゾフェノン誘導体 |
| KR101264456B1 (ko) * | 2005-05-31 | 2013-05-14 | 디에스엠 아이피 어셋츠 비.브이. | 새로운 폴리실록세인 자외선차단제 |
-
2007
- 2007-02-06 JP JP2008553748A patent/JP5294877B2/ja not_active Expired - Fee Related
- 2007-02-06 WO PCT/EP2007/051117 patent/WO2007090832A1/en active Application Filing
- 2007-02-06 EP EP07726317.6A patent/EP1981895B1/en active Active
- 2007-02-06 US US12/223,686 patent/US7999128B2/en not_active Expired - Fee Related
- 2007-02-06 ES ES07726317.6T patent/ES2584204T3/es active Active
- 2007-02-07 GB GB0702326A patent/GB2435041A/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JP5294877B2 (ja) | 2013-09-18 |
| GB0702326D0 (en) | 2007-03-21 |
| WO2007090832A1 (en) | 2007-08-16 |
| US7999128B2 (en) | 2011-08-16 |
| JP2009526015A (ja) | 2009-07-16 |
| EP1981895B1 (en) | 2016-04-27 |
| US20090220439A1 (en) | 2009-09-03 |
| EP1981895A1 (en) | 2008-10-22 |
| GB2435041A (en) | 2007-08-15 |
| GB2435041A9 (en) | 2007-08-15 |
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