DE19651057A1 - Stabilised light-protection composition, e.g. for cosmetic use - Google Patents
Stabilised light-protection composition, e.g. for cosmetic useInfo
- Publication number
- DE19651057A1 DE19651057A1 DE1996151057 DE19651057A DE19651057A1 DE 19651057 A1 DE19651057 A1 DE 19651057A1 DE 1996151057 DE1996151057 DE 1996151057 DE 19651057 A DE19651057 A DE 19651057A DE 19651057 A1 DE19651057 A1 DE 19651057A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- tris
- derivatives
- preparations
- isofol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000002537 cosmetic Substances 0.000 title claims description 23
- 239000000203 mixture Substances 0.000 title description 16
- 150000001298 alcohols Chemical class 0.000 claims abstract description 23
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims description 24
- NPSJHQMIVNJLNN-UHFFFAOYSA-N 2-ethylhexyl 4-nitrobenzoate Chemical compound CCCCC(CC)COC(=O)C1=CC=C([N+]([O-])=O)C=C1 NPSJHQMIVNJLNN-UHFFFAOYSA-N 0.000 claims description 13
- 239000004808 2-ethylhexylester Substances 0.000 claims description 13
- 239000007983 Tris buffer Substances 0.000 claims description 13
- NGJJZCPADSICRI-UHFFFAOYSA-N 4-[[4,6-bis(4-carboxyanilino)-1,3,5-triazin-2-yl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N=C(NC(=NC=1C=CC(=CC=1)C(O)=O)N1)NC1=NC1=CC=C(C(O)=O)C=C1 NGJJZCPADSICRI-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 230000000475 sunscreen effect Effects 0.000 claims description 7
- 239000000516 sunscreening agent Substances 0.000 claims description 7
- XMVBHZBLHNOQON-UHFFFAOYSA-N 2-butyl-1-octanol Chemical compound CCCCCCC(CO)CCCC XMVBHZBLHNOQON-UHFFFAOYSA-N 0.000 claims description 6
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000004611 light stabiliser Substances 0.000 claims description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- JGUMTYWKIBJSTN-UHFFFAOYSA-N 2-ethylhexyl 4-[[4,6-bis[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)OCC(CC)CCCC)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 JGUMTYWKIBJSTN-UHFFFAOYSA-N 0.000 abstract description 24
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000011814 protection agent Substances 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 72
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 239000002304 perfume Substances 0.000 description 25
- 239000003755 preservative agent Substances 0.000 description 25
- 230000002335 preservative effect Effects 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 229920002125 Sokalan® Polymers 0.000 description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 18
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- 235000011187 glycerol Nutrition 0.000 description 15
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 14
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- 239000003921 oil Substances 0.000 description 14
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- 239000000126 substance Substances 0.000 description 14
- HEOCBCNFKCOKBX-RELGSGGGSA-N (1s,2e,4r)-4,7,7-trimethyl-2-[(4-methylphenyl)methylidene]bicyclo[2.2.1]heptan-3-one Chemical compound C1=CC(C)=CC=C1\C=C/1C(=O)[C@]2(C)CC[C@H]\1C2(C)C HEOCBCNFKCOKBX-RELGSGGGSA-N 0.000 description 13
- 235000021355 Stearic acid Nutrition 0.000 description 12
- 229960004697 enzacamene Drugs 0.000 description 12
- 239000006210 lotion Substances 0.000 description 12
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 12
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 12
- 239000008117 stearic acid Substances 0.000 description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 12
- REZOIPSCCRVWNN-UHFFFAOYSA-N tetratriacontan-17-ol Chemical compound CCCCCCCCCCCCCCCCCC(O)CCCCCCCCCCCCCCCC REZOIPSCCRVWNN-UHFFFAOYSA-N 0.000 description 12
- 239000012071 phase Substances 0.000 description 11
- XULHFMYCBKQGEE-UHFFFAOYSA-N 2-hexyl-1-Decanol Chemical compound CCCCCCCCC(CO)CCCCCC XULHFMYCBKQGEE-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 9
- 230000005855 radiation Effects 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 8
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 8
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 7
- 239000003963 antioxidant agent Substances 0.000 description 7
- 235000006708 antioxidants Nutrition 0.000 description 7
- 239000004205 dimethyl polysiloxane Substances 0.000 description 7
- 229940075529 glyceryl stearate Drugs 0.000 description 7
- 150000002632 lipids Chemical class 0.000 description 7
- 229920002545 silicone oil Polymers 0.000 description 7
- DSEKYWAQQVUQTP-XEWMWGOFSA-N (2r,4r,4as,6as,6as,6br,8ar,12ar,14as,14bs)-2-hydroxy-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1h-picen-3-one Chemical compound C([C@H]1[C@]2(C)CC[C@@]34C)C(C)(C)CC[C@]1(C)CC[C@]2(C)[C@H]4CC[C@@]1(C)[C@H]3C[C@@H](O)C(=O)[C@@H]1C DSEKYWAQQVUQTP-XEWMWGOFSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
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- 150000003839 salts Chemical class 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
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- 150000001875 compounds Chemical class 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- DLAHAXOYRFRPFQ-UHFFFAOYSA-N dodecyl benzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=CC=C1 DLAHAXOYRFRPFQ-UHFFFAOYSA-N 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
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- 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 3
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- CQOVPNPJLQNMDC-UHFFFAOYSA-N N-beta-alanyl-L-histidine Natural products NCCC(=O)NC(C(O)=O)CC1=CN=CN1 CQOVPNPJLQNMDC-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 3
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- 238000011105 stabilization Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- ARCJQKUWGAZPFX-UHFFFAOYSA-N stilbene oxide Chemical compound O1C(C=2C=CC=CC=2)C1C1=CC=CC=C1 ARCJQKUWGAZPFX-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/342—Alcohols having more than seven atoms in an unbroken chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4966—Triazines or their condensed derivatives
-
- 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
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
Abstract
Description
Die vorliegende Erfindung betrifft kosmetische und dermatologische Lichtschutzzuberei tungen, insbesondere hautpflegende kosmetische und dermatologische Lichtschutzzu bereitungen.The present invention relates to cosmetic and dermatological light protection tions, in particular skincare cosmetic and dermatological sunscreen preparations.
Die schädigende Wirkung des ultravioletten Teils der Sonnenstrahlung auf die Haut ist allgemein bekannt. Während Strahlen mit einer Wellenlänge, die kleiner als 290 nm ist (der sogenannte UVC-Bereich), von der Ozonschicht in der Erdatmosphäre absorbiert werden, verursachen Strahlen im Bereich zwischen 290 nm und 320 nm, dem soge nannten UVB-Bereich, ein Erythem, einen einfachen Sonnenbrand oder sogar mehr oder weniger starke Verbrennungen.The damaging effect of the ultraviolet part of solar radiation on the skin is well known. While rays with a wavelength smaller than 290 nm (the so-called UVC range), absorbed by the ozone layer in the earth's atmosphere be, cause rays in the range between 290 nm and 320 nm, the soge called UVB, erythema, simple sunburn or even more or less severe burns.
Als ein Maximum der Erythemwirksamkeit des Sonnenlichtes wird der engere Bereich um 308 nm angegeben.As a maximum of the erythema efficiency of sunlight becomes the narrower area indicated at 308 nm.
Zum Schutze gegen UVB-Strahlung sind zahlreiche Verbindungen bekannt, bei denen es sich zumeist um Derivate des 3-Benzylidencamphers, der 4-Aminobenzoesäure, der Zimtsäure, der Salicylsäure, des Benzophenons sowie auch des 2-Phenylbenzimidazols handelt.To protect against UVB radiation, numerous compounds are known in which It is mostly derivatives of 3-Benzylidencamphers, the 4-aminobenzoic acid, the Cinnamic acid, salicylic acid, benzophenone and 2-phenylbenzimidazole is.
Auch für den Bereich zwischen etwa 320 nm und etwa 400 nm, den sogenannten UVA- Bereich, ist es wichtig, Filtersubstanzen zur Verfügung zu haben, da auch dessen Strahlen Schäden hervorrufen können. So ist erwiesen, daß UVA-Strahlung zu einer Schädigung der elastischen und kollagenen Fasern des Bindegewebes führt, was die Haut vorzeitig altern läßt, und daß sie als Ursache zahlreicher phototoxischer und pho toallergischer Reaktionen zu sehen ist. Der schädigende Einfluß der UVB-Strahlung kann durch UVA-Strahlung verstärkt werden.Also for the range between about 320 nm and about 400 nm, the so-called UVA Area, it is important to have filter substances available as well Radiation can cause damage. So it is proven that UVA radiation to a Damage to the elastic and collagen fibers of the connective tissue leads to what the Skin ages prematurely, and that they are the cause of numerous phototoxic and pho allergic reactions can be seen. The damaging influence of UVB radiation can be amplified by UVA radiation.
Die UV-Strahlung kann aber auch zu photochemischen Reaktionen führen, wobei dann die photochemischen Reaktionsprodukte in den Hautmetabolismus eingreifen.The UV radiation can also lead to photochemical reactions, in which case the photochemical reaction products interfere with the skin metabolism.
Vorwiegend handelt es sich bei solchen photochemischen Reaktionsprodukten um radi kalische Verbindungen, z. B. Hydroxylradikale. Auch undefinierte radikalische Photopro dukte, welche in der Haut selbst entstehen, können aufgrund ihrer hohen Reaktivität un kontrollierte Folgereaktionen an den Tag legen. Aber auch Singulettsauerstoff, ein nichtradikalischer angeregter Zustand des Sauerstoffmoleküls kann bei UV-Bestrahlung auftreten, ebenso kurzlebige Epoxide und viele Andere. Singulettsauerstoff beispiels weise zeichnet sich gegenüber dem normalerweise vorliegenden Triplettsauerstoff (radikalischer Grundzustand) durch gesteigerte Reaktivität aus. Allerdings existieren auch angeregte, reaktive (radikalische) Triplettzustände des Sauerstoffmoleküls.Predominantly, such photochemical reaction products are radi kalische connections, z. B. hydroxyl radicals. Also undefined radical Photopro Due to their high reactivity, unreacted substances which are formed in the skin itself controlled controlled reactions to the day. But also singlet oxygen, a Non-radical excited state of the oxygen molecule can under UV irradiation occur, as are short-lived epoxides and many others. Singlet oxygen, for example is distinguished from the normally existing triplet oxygen (radical ground state) by increased reactivity. However exist also excited, reactive (radical) triplet states of the oxygen molecule.
Ferner zählt UV-Strahlung zur ionisierenden Strahlung. Es besteht also das Risiko, daß auch ionische Spezies bei UV-Exposition entstehen, welche dann ihrerseits oxidativ in die biochemischen Prozesse einzugreifen vermögen.Furthermore, UV radiation counts as ionizing radiation. So there is a risk that also arise ionic species on UV exposure, which in turn oxidative in to be able to intervene in the biochemical processes.
Ein vorteilhafter UVB-Filter ist der 4,4',4''-(1,3,5-Triazin-2,4,6-triyltriimino)-tris-benzoe
säure-tris(2-ethylhexylester), synonym: 2,4,6-Tris-[anilino-(p-carbo-2'-ethyl-1'-hexyloxy)]-
1,3,5-triazin.
An advantageous UVB filter is the 4,4 ', 4 "- (1,3,5-triazine-2,4,6-triyltriimino) -tris-benzoic acid tris (2-ethylhexyl ester), synonymous: 2, 4,6-tris [anilino (p-carbo-2'-ethyl-1'-hexyloxy)] - 1,3,5-triazine.
Diese UVB-Filtersubstanz wird von der BASF Aktiengesellschaft unter der Warenbe zeichnung UVINUL® T 150 vertrieben und zeichnet sich durch gute UV-Absorptionsei genschaften aus.This UVB filter substance is sold by BASF Aktiengesellschaft under Warenbe UVINUL® T 150 is sold and is characterized by good UV absorption properties.
Der Hauptnachteil dieses UVB-Filters ist die schlechte Löslichkeit in Lipiden. Bekannte Lösungsmittel für diesen UVB-Filter können maximal ca. 15 Gew.-% dieses Filters lo sen, entsprechend etwa 1-1,5 Gew.-% gelöster, und damit aktiver, UV-Filtersubstanz.The main disadvantage of this UVB filter is the poor solubility in lipids. Known Solvents for this UVB filter can not exceed about 15% by weight of this filter corresponding to about 1-1.5 wt .-% dissolved, and thus active, UV filter substance.
Die Verwendung von Guerbet-Alkoholen in Kosmetika ist an sich bekannt. Sie zeichnen
sich durch die Struktur
The use of Guerbet alcohols in cosmetics is known per se. They are characterized by the structure
aus. Dabei bedeuten R1 und R2 in der Regel unverzweigte Alkylreste.out. R 1 and R 2 are generally unbranched alkyl radicals.
Es war indes überraschend und für den Fachmann nicht vorauszusehen, daß licht
schutzwirksame Wirkstoffkombinationen aus 4,4',4''-(1,3,5-Triazin-2,4,6-triyltriimino)-tris
benzoesäure-tris(2-ethylhexylester) und Guerbet-Alkoholen der Struktur
It was, however, surprising and not foreseeable for the skilled person that light-protective active ingredient combinations of 4,4 ', 4''- (1,3,5-triazine-2,4,6-triyltriimino) -tris benzoic acid tris (2- ethylhexyl ester) and Guerbet alcohols of the structure
wobei R1 und R2 unverzweigte Alkylreste mit 2 bis 18 Kohlenstoffatomen bedeuten, bzw.
die Verwendung von Guerbet-Alkoholen der Struktur
where R 1 and R 2 are unbranched alkyl radicals having 2 to 18 carbon atoms, or the use of Guerbet alcohols of the structure
wobei R1 und R2 unverzweigte Alkylreste mit 2 bis 18 Kohlenstoffatomen bedeuten als Lösungsmittel, Lösungsvermittler oder Solubilisator für 4,4',4''-(1,3,5-Triazin-2,4,6-triyltri imino)-tris-benzoesäure-tris(2-ethylhexylester), insbesondere für die Verwendung in Lichtschutzmitteln, den Nachteilen des Standes der Technik Abhilfe schaffen würden. where R 1 and R 2 are unbranched alkyl radicals having 2 to 18 carbon atoms as solvent, solubilizer or solubilizer for 4,4 ', 4''- (1,3,5-triazine-2,4,6-triyltriimino) tris benzoic acid tris (2-ethylhexyl ester), especially for use in light stabilizers, would remedy the disadvantages of the prior art.
Es ist erfindungsgemäß möglich die Einsatzmengen von 4,4',4''-(1,3,5-Triazin-2,4,6-triyl triimino)-tris-benzoesäure-tris(2-ethylhexylester) in kosmetischen oder dermatologischen Zubereitungen gegenüber dem Stande der Technik zu verdoppeln.It is possible according to the invention the amounts of 4,4 ', 4' '- (1,3,5-triazine-2,4,6-triyl triimino) tris-benzoic acid tris (2-ethylhexyl ester) in cosmetic or dermatological Preparations over the prior art to double.
Es war erstaunlich, daß durch Zugabe von Isofol 16 eine Stabilisierung von Lösungen des 4,4',4''-( 1,3,5-Triazin-2,4,6-triyltriimino)-tris-benzoesäure-tris(2-ethylhexylester) be wirkt wird, da die letztere Substanz nicht nur schlechte Löslichkeit aufweist, sondern auch aus seiner Lösung leicht wieder auskristallisiert. Erfindungsgemäß ist daher auch ein Verfahren zur Stabilisierung von Lösungen des 4,4',4''-(1,3,5-Triazin-2,4,6-triyltriimi no)-tris-benzoesäure-tris(2-ethylhexylester), dadurch gekennzeichnet, daß solchen Lö sungen ein wirksamer Gehalt an Guerbet-Alkoholen zugesetzt wird.It was amazing that by adding Isofol 16 a stabilization of solutions of 4,4 ', 4 "- (1,3,5-triazine-2,4,6-triyltriimino) -tris-benzoic acid tris (2-ethylhexyl ester) be acts because the latter substance not only has poor solubility, but also easily crystallized from its solution again. Therefore, according to the invention also a method of stabilizing solutions of the 4,4 ', 4' '- (1,3,5-triazine-2,4,6-triyltrimi no) tris-benzoic acid tris (2-ethylhexyl ester), characterized in that such Lö an effective Guerbet alcohol content is added.
Die Gesamtmenge an 4,4',4''-(1,3,5-Triazin-2,4,6-triyltriimino)-tris-benzoesäure-tris(2- ethylhexylester) in den fertigen kosmetischen oder dermatologischen Zubereitungen wird vorteilhaft aus dem Bereich von 0,1-10,0 Gew.-%, bevorzugt 0,5-6,0 Gew.-% gewählt, bezogen auf das Gesamtgewicht der Zubereitungen.The total amount of 4,4 ', 4' '- (1,3,5-triazine-2,4,6-triyltriimino) -tris-benzoic acid tris (2- ethylhexyl ester) in the finished cosmetic or dermatological preparations is advantageously from the range of 0.1-10.0 wt .-%, preferably 0.5-6.0 wt .-% chosen, based on the total weight of the preparations.
Erfindungsgemäß vorteilhaft werden der oder die Guerbet-Alkohole gewählt aus der
Gruppe, bei denen
R1 = Propyl, Butyl, Pentyl, Hexyl, Heptyl oder Octyl und
R2 = Hexyl, Heptyl, Octyl, Nonyl, Decyl, Undecyl, Dodecyl, Tridecyl oder Tetradecyl.Advantageously according to the invention, the Guerbet alcohol or alcohols are selected from the group in which
R 1 = propyl, butyl, pentyl, hexyl, heptyl or octyl and
R 2 = hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl or tetradecyl.
Erfindungsgemäß bevorzugte Guerbet-Alkohole sind das 2-Butyloctanol - es hat die
chemische Struktur
Guerbet alcohols preferred according to the invention are the 2-butyloctanol - it has the chemical structure
und ist beispielsweise unter der Handelsbezeichnung Isofol® 12 von der Gesellschaft
Dondea Chemie GmbH erhältlich - und das 2-Hexyldecanol - es hat die chemische
Struktur
and is available, for example, under the trade name Isofol® 12 from Dondea Chemie GmbH - and 2-hexyldecanol - it has the chemical structure
und ist beispielsweise unter der Handelsbezeichnung Isofol® 16 von der Gesellschaft Condea Chemie GmbH erhältlich.and is, for example, under the trade name Isofol® 16 from the Company Condea Chemie GmbH available.
Auch Mischungen von erfindungsgemäßen Guerbet-Alkoholen sind erfindungsgemäß vorteilhaft zu verwenden. Mischungen aus 2-Butyloctanol und 2-Hexyldecanol sind bei spielsweise unter der Handelsbezeichnung Isofol® 14 von der Gesellschaft Condea Chemie GmbH erhältlich.Mixtures of Guerbet alcohols according to the invention are also in accordance with the invention advantageous to use. Mixtures of 2-butyloctanol and 2-hexyldecanol are included For example, under the trade name Isofol® 14 of the company Condea Chemie GmbH available.
Die Gesamtmenge an Guerbet-Alkoholen in den fertigen kosmetischen oder dermatolo gischen Zubereitungen wird vorteilhaft aus dem Bereich von 0,1-25,0 Gew.-%, bevor zugt 0,5-15,0 Gew.-% gewählt, bezogen auf das Gesamtgewicht der Zubereitungen.The total amount of Guerbet alcohols in the finished cosmetic or dermatolo Advantageous formulations are advantageously from the range of 0.1-25.0 wt .-%, before zugt 0.5-15.0 wt .-% selected, based on the total weight of the preparations.
Es ist von Vorteil, Gewichtsverhältnisse von 4,4',4''-(1,3,5-Triazin-2,4,6-triyltriimino)-tris benzoesäure-tris(2-ethylhexylester) und Guerbet-Alkoholen aus dem Bereich von 1 : 10 bis 10 : 1, bevorzugt 1 : 4 bis 4 : 1, zu wählen.It is advantageous to weight ratios of 4,4 ', 4' '- (1,3,5-triazine-2,4,6-triyltriimino) tris benzoic acid tris (2-ethylhexyl ester) and Guerbet alcohols in the range of 1:10 to 10: 1, preferably 1: 4 to 4: 1, to choose.
Erfindungsgemäße kosmetische und dermatologische Zubereitungen enthalten vorteil haft außerdem anorganische Pigmente auf Basis von Metalloxiden und/oder anderen in Wasser schwerlöslichen oder unlöslichen Metallverbindungen, insbesondere der Oxide des Titans (TiO2), Zinks (ZnO), Eisens (z. B. Fe2O3), Zirkoniums (ZrO2), Siliciums (SiO2), Mangans (z. B. MnO), Aluminiums (Al2O3), Cers (z. B. Ce2O3), Mischoxiden der entspre chenden Metalle sowie Abmischungen aus solchen Oxiden. Besonders bevorzugt han delt es sich um Pigmente auf der Basis von TiO2.Cosmetic and dermatological preparations according to the invention also advantageously contain inorganic pigments based on metal oxides and / or other sparingly soluble or insoluble metal compounds, in particular the oxides of titanium (TiO 2 ), zinc (ZnO), iron (eg Fe 2 O) 3 ), zirconium (ZrO 2 ), silicon (SiO 2 ), manganese (eg MnO), aluminum (Al 2 O 3 ), cerium (eg Ce 2 O 3 ), mixed oxides of the corresponding metals and Blends of such oxides. Particular preference is given to pigments based on TiO 2 .
Es ist besonders vorteilhaft im Sinne der vorliegenden Erfindung, wenngleich nicht zwin gend, wenn die anorganischen Pigmente in hydrophober Form vorliegen, d. h., daß sie oberflächlich wasserabweisend behandelt sind. Diese Oberflächenbehandlung kann darin bestehen, daß die Pigmente nach an sich bekannten Verfahren mit einer dünnen hydrophoben Schicht versehen werden. It is particularly advantageous in the context of the present invention, although not zwin when the inorganic pigments are in hydrophobic form, d. h. that she are superficially treated water-repellent. This surface treatment can consist in that the pigments according to known methods with a thin be provided hydrophobic layer.
Eines solcher Verfahren besteht beispielsweise darin, daß die hydrophobe Oberflächen
schicht nach einer Rektion gemäß
One such method is, for example, that the hydrophobic surface layer according to a reaction according to
n TiO2 + m (RO)3 Si-R' → n TiO2 (oberfl.)n TiO 2 + m (RO) 3 Si-R '→ n TiO 2 (surface)
erzeugt wird. n und m sind dabei nach Belieben einzusetzende stöchiometrische Para meter, R und R' die gewünschten organischen Reste. Beispielsweise in Analogie zu DE- OS 33 14 742 dargestellte hydrophobisierte Pigmente sind von Vorteil.is produced. n and m are random stoichiometric parameters meter, R and R 'are the desired organic radicals. For example, in analogy to DE OS 33 14 742 illustrated hydrophobized pigments are advantageous.
Vorteilhafte TiO2-Pigmente sind beispielsweise unter den Handelsbezeichnungen MT 100 T von der Firma TAYCA, ferner M 160 von der Firma Kemira sowie T 805 von der Firma Degussa erhältlich.Advantageous TiO 2 pigments are available, for example, under the trade names MT 100 T from TAYCA, furthermore M 160 from Kemira and T 805 from Degussa.
Die erfindungsgemäßen kosmetischen und/oder dermatologischen Lichtschutzformulie rungen können wie üblich zusammengesetzt sein und dem kosmetischen und/oder der matologischen Lichtschutz, ferner zur Behandlung, der Pflege und der Reinigung der Haut und/oder der Haare und als Schminkprodukt in der dekorativen Kosmetik dienen.The cosmetic and / or dermatological sunscreen formulation according to the invention ments may be composed as usual and the cosmetic and / or the Photological light protection, furthermore for the treatment, care and cleaning of the Skin and / or hair and serve as a make-up product in decorative cosmetics.
Zur Anwendung werden die erfindungsgemäßen kosmetischen und dermatologischen Zubereitungen in der für Kosmetika üblichen Weise auf die Haut und/oder die Haare in ausreichender Menge aufgebracht.For use, the cosmetic and dermatological according to the invention Preparations in the usual way for cosmetics on the skin and / or hair in applied sufficient amount.
Besonders bevorzugt sind solche kosmetischen und dermatologischen Zubereitungen, die in der Form eines Sonnenschutzmittels vorliegen. Vorteilhaft können diese zusätzlich mindestens einen weiteren UVA-Filter und/oder mindestens einen weiteren UVB-Filter und/oder mindestens ein anorganisches Pigment, bevorzugt ein anorganisches Mikro pigment, enthalten.Particularly preferred are such cosmetic and dermatological preparations, which are in the form of a sunscreen. Advantageously, these can additionally at least one further UVA filter and / or at least one further UVB filter and / or at least one inorganic pigment, preferably an inorganic micro pigment, included.
Die erfindungsgemäßen kosmetischen und dermatologischen Zubereitungen können kosmetische Hilfsstoffe enthalten, wie sie üblicherweise in solchen Zubereitungen ver wendet werden, z. B. Konservierungsmittel, Bakterizide, Parfüme, Substanzen zum Ver hindern des Schäumens, Farbstoffe, Pigmente, die eine färbende Wirkung haben, Ver dickungsmittel, anfeuchtende und/oder feuchthaltende Substanzen, Fette, Öle, Wachse oder andere übliche Bestandteile einer kosmetischen oder dermatologischen Formulie rung wie Alkohole, Polyole, Polymere, Schaumstabilisatoren, Elektrolyte, organische Lösungsmittel oder Silikonderivate.The cosmetic and dermatological preparations according to the invention can contain cosmetic excipients, as ver usually in such preparations ver be used, for. As preservatives, bactericides, perfumes, substances for Ver foaming, dyes, pigments having a coloring effect, Ver thickeners, moisturizing and / or moisturizing substances, fats, oils, waxes or other common ingredients of a cosmetic or dermatological formulation Such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic Solvent or silicone derivatives.
Ein zusätzlicher Gehalt an Antioxidantien ist im allgemeinen bevorzugt. Erfindungsge mäß können als günstige Antioxidantien alle für kosmetische und/oder dermatologische Anwendungen geeigneten oder gebräuchlichen Antioxidantien verwendet werden.An additional content of antioxidants is generally preferred. Erfindungsge As favorable antioxidants, they can all be used for cosmetic and / or dermatological purposes Applications of suitable or common antioxidants can be used.
Vorteilhaft werden die Antioxidantien gewählt aus der Gruppe bestehend aus Aminosäu ren (z. B. Glycin, Histidin, Tyrosin, Tryptophan) und deren Derivate, Imidazole (z. B. Uro caninsäure) und deren Derivate, Peptide wie D,L-Carnosin, D-Carnosin, L-Carnosin und deren Derivate (z. B. Anserin), Carotinoide, Carotine (z. B. α-Carotin, β-Carotin, Lycopin) und deren Derivate, Chlorogensäure und deren Derivate, Liponsäure und deren Deri vate (z. B. Dihydroliponsäure), Aurothioglucose, Propylthiouracil und andere Thiole (z. B. Thioredoxin, Glutathion, Cystein, Cystin, Cystamin und deren Glycosyl-, N-Acetyl-, Methyl-, Ethyl-, Propyl-, Amyl-, Butyl- und Lauryl-, Palmitoyl-, Oleyl-, γ-Linoleyl-, Chole steryl- und Glycerylester) sowie deren Salze, Dilaurylthiodipropionat, Distearylthiodi propionat, Thiodipropionsäure und deren Derivate (Ester, Ether, Peptide, Lipide, Nukleo tide, Nukleoside und Salze) sowie Sulfoximinverbindungen (z. B. Buthioninsulfoximine, Homocysteinsulfoximin, Buthioninsulfone, Penta-, Hexa-, Heptathioninsulfoximin) in sehr geringen verträglichen Dosierungen (z. B. µmol bis µmol/kg), ferner (Metall)-Chelatoren (z. B. α-Hydroxyfettsäuren, Palmitinsäure, Phytinsäure, Lactoferrin), α-Hydroxysäuren (z. B. Citronensäure, Milchsäure, Apfelsäure), Huminsäure, Gallensäure, Gallenextrakte, Bilirubin, Biliverdin, EDTA, EGTA und deren Derivate, ungesättigte Fettsäuren und de ren Derivate (z. B. γ-Linolensäure, Linolsäure, Ölsäure), Folsäure und deren Derivate, Furfurylidensorbitol und dessen Derivate, Ubichinon und Ubichinol und deren Derivate, Vitamin C und Derivate (z. B. Ascorbylpalmitat, Mg-Ascorbylphosphat, Ascorbylacetat), Tocopherole und Derivate (z. B. Vitamin-E-acetat), Vitamin A und Derivate (Vitamin-A- palmitat) sowie Koniferylbenzoat des Benzoeharzes, Rutinsäure und deren Derivate, α-Glycosylrutin, Ferulasäure, Furfurylidenglucitol, Carnosin, Butylhydroxytoluol, Butylhy droxyanisol, Nordihydroguajakharzsäure, Nordihydroguajaretsäure, Trihydroxybutyro phenon, Harnsäure und deren Derivate, Mannose und deren Derivate, Zink und dessen Derivate (z. B. ZnO, ZnSO4) Selen und dessen Derivate (z. B. Selenmethionin), Stilbene und deren Derivate (z. B. Stilbenoxid, Trans-Stilbenoxid) und die erfindungsgemäß ge eigneten Derivate (Salze, Ester, Ether, Zucker, Nukleotide, Nukleoside, Peptide und Lipide) dieser genannten Wirkstoffe. Advantageously, the antioxidants are selected from the group consisting of amino acids (eg glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (eg urotroic acid) and their derivatives, peptides such as D, L-carnosine, D-carnosine, L-carnosine and their derivatives (eg anserine), carotenoids, carotenes (eg α-carotene, β-carotene, lycopene) and their derivatives, chlorogenic acid and its derivatives, lipoic acid and derivatives thereof (eg dihydrolipoic acid), aurothioglucose, propylthiouracil and other thiols (eg thioredoxin, glutathione, cysteine, cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, Butyl and lauryl, palmitoyl, oleyl, γ-linoleyl, cholesterol and glyceryl esters) and their salts, dilauryl thiodipropionate, distearyl thiodi propionate, thiodipropionic acid and derivatives thereof (esters, ethers, peptides, lipids, nucleotides, nucleosides and Salts) as well as sulfoximine compounds (eg buthionine sulfoximines, homocysteinesulfoximine, buthione insulfone, penta, hexa, heptathionine sulfoximine) in very low tolerated dosages (eg. Μmol to μmol / kg), furthermore (metal) chelators (eg α-hydroxyfatty acids, palmitic acid, phytic acid, lactoferrin), α-hydroxy acids (eg citric acid, lactic acid, malic acid), humic acid, bile acid, Bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives (eg γ-linolenic acid, linoleic acid, oleic acid), folic acid and its derivatives, furfurylidenesorbitol and its derivatives, ubiquinone and ubiquinol and derivatives thereof, Vitamin C and derivatives (eg, ascorbyl palmitate, Mg ascorbyl phosphate, ascorbyl acetate), tocopherols and derivatives (eg, vitamin E acetate), vitamin A and derivatives (vitamin A palmitate), and benzylic resin, benzylic acid, rutinic acid and their derivatives, α-glycosylrutin, ferulic acid, furfurylidenglucitol, carnosine, butylhydroxytoluene, butylhydroxyanisole, nordihydroguaiacetic acid, nordihydroguiaretic acid, trihydroxybutyrone, uric acid and its derivatives, mannose and derivatives thereof, Zinc and its derivatives (eg. ZnO, ZnSO 4 ) selenium and its derivatives (eg selenium methionine), stilbenes and their derivatives (eg stilbene oxide, trans-stilbene oxide) and the inventively suitable derivatives (salts, esters, ethers, sugars, nucleotides , Nucleosides, peptides and lipids) of these drugs.
Die Menge der vorgenannten Antioxidantien (eine oder mehrere Verbindungen) in den Zubereitungen beträgt vorzugsweise 0,001 bis 30 Gew.-%, besonders bevorzugt 0,05- 20 Gew.-%, insbesondere 1-10 Gew.-%, bezogen auf das Gesamtgewicht der Zuberei tung.The amount of the aforementioned antioxidants (one or more compounds) in the Preparations is preferably from 0.001 to 30% by weight, particularly preferably from 0.05 to 20 wt .-%, in particular 1-10 wt .-%, based on the total weight of Zuberei tung.
Sofern Vitamin E und/oder dessen Derivate das oder die Antioxidantien darstellen, ist vorteilhaft, deren jeweilige Konzentrationen aus dem Bereich von 0,001-10 Gew.-%, bezogen auf das Gesamtgewicht der Formulierung, zu wählen.If vitamin E and / or its derivatives are the antioxidant (s) advantageous, their respective concentrations in the range of 0.001-10 wt .-%, based on the total weight of the formulation to choose.
Sofern Vitamin A, bzw. Vitamin-A-Derivate, bzw. Carotine bzw. deren Derivate das oder die Antioxidantien darstellen, ist vorteilhaft, deren jeweilige Konzentrationen aus dem Bereich von 0,001-10 Gew.-%, bezogen auf das Gesamtgewicht der Formulierung, zu wählen.If vitamin A, or vitamin A derivatives, or carotenes or their derivatives, the or which are antioxidants is advantageous, their respective concentrations from the Range of 0.001-10% by weight based on the total weight of the formulation choose.
Die Lipidphase kann vorteilhaft gewählt werden aus folgender Substanzgruppe:
The lipid phase can advantageously be selected from the following substance group:
- - Mineralöle, Mineralwachse- mineral oils, mineral waxes
- - Öle, wie Triglyceride der Caprin- oder der Caprylsäure, vorzugsweise aber Rizi nusöl;- Oils, such as triglycerides of capric or caprylic acid, but preferably Rizi nusöl;
- - Fette, Wachse und andere natürliche und synthetische Fettkörper, vorzugsweise Ester von Fettsäuren mit Alkoholen niedriger C-Zahl, z. B. mit Isopropanol, Propy lenglykol oder Glycerin, oder Ester von Fettalkoholen mit Alkansäuren niedriger C-Zahl oder mit Fettsäuren;- Fats, waxes and other natural and synthetic fats, preferably Esters of fatty acids with lower C-number alcohols, e.g. B. with isopropanol, propy glycol or glycerol, or esters of fatty alcohols with lower alkanoic acids C number or with fatty acids;
- - Alkylbenzoate;- alkyl benzoates;
- - Silikonöle wie Dimethylpolysiloxane, Diethylpolysiloxane, Diphenylpolysiloxane sowie Mischformen daraus.- Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and mixed forms thereof.
Die Ölphase der Emulsionen, Oleogele bzw. Hydrodispersionen oder Lipodispersionen im Sinne der vorliegenden Erfindung wird vorteilhaft gewählt aus der Gruppe der Ester aus gesättigten und/oder ungesättigten, verzweigten und/oder unverzweigten Alkancar bonsäuren einer Kettenlänge von 3 bis 30 C-Atomen und gesättigten und/oder ungesät tigten, verzweigten und/oder unverzweigten Alkoholen einer Kettenlänge von 3 bis 30 C- Atomen, aus der Gruppe der Ester aus aromatischen Carbonsäuren und gesättigten und/oder ungesättigten, verzweigten und/oder unverzweigten Alkoholen einer Ketten länge von 3 bis 30 C-Atomen. Solche Esteröle können dann vorteilhaft gewählt werden aus der Gruppe Isopropylmyristat, Isopropylpalmitat, Isopropylstearat, Isopropyloleat, n- Butylstearat, n-Hexyllaurat, n-Decyloleat, Isooctylstearat, Isononylstearat, Isononyliso nonanoat, 2-Ethylhexylpalmitat, 2-Ethylhexyllaurat, 2-Hexyldecylstearat, 2-Octyldodecyl palmitat, Oleyloleat, Oleylerucat, Erucyloleat, Erucylerucat sowie synthetische, halbsyn thetische und natürliche Gemische solcher Ester, z. B. Jojobaöl.The oil phase of the emulsions, oleogels or hydrodispersions or lipodispersions For the purposes of the present invention is advantageously selected from the group of esters from saturated and / or unsaturated, branched and / or unbranched Alkancar bonsäuren a chain length of 3 to 30 carbon atoms and saturated and / or unsatd saturated, branched and / or unbranched alcohols of a chain length of 3 to 30 C Atoms, from the group of esters of aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols of a chain length of 3 to 30 carbon atoms. Such ester oils can then be chosen advantageously from the group isopropyl myristate, isopropyl palmitate, isopropyl stearate, isopropyl oleate, n- Butyl stearate, n-hexyl laurate, n-decyl oleate, isooctyl stearate, isononyl stearate, isononyl iso nonanoate, 2-ethylhexyl palmitate, 2-ethylhexyl laurate, 2-hexyldecyl stearate, 2-octyldodecyl palmitate, oleyl oleate, oleyl erucate, erucyl oleate, erucyl erucate, and synthetic, semysin thetic and natural mixtures of such esters, e.g. B. jojoba oil.
Ferner kann die Ölphase vorteilhaft gewählt werden aus der Gruppe der verzweigten und unverzweigten Kohlenwasserstoffe und -wachse, der Silkonöle, der Dialkylether, der Gruppe der gesättigten oder ungesättigten, verzweigten oder unverzweigten Alkoho le, sowie der Fettsäuretriglyceride, namentlich der Triglycerinester gesättigter und/oder ungesättigter, verzweigter und/oder unverzweigter Alkancarbonsäuren einer Kettenlän ge von 8 bis 24, insbesondere 12-18 C-Atomen. Die Fettsäuretriglyceride können bei spielsweise vorteilhaft gewählt werden aus der Gruppe der synthetischen, halbsyntheti schen und natürlichen Öle, z. B. Olivenöl, Sonnenblumenöl, Sojaöl, Erdnußöl, Rapsöl, Mandelöl, Palmöl, Kokosöl, Palmkernöl und dergleichen mehr.Furthermore, the oil phase can be advantageously selected from the group of branched and unbranched hydrocarbons and waxes, the silicone oils, the dialkyl ethers, the group of saturated or unsaturated, branched or unbranched alcohols le, as well as the fatty acid triglycerides, namely the triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids of a chain length ge from 8 to 24, in particular 12-18 C-atoms. The fatty acid triglycerides may be included For example, be advantageously selected from the group of synthetic, semisyntheti and natural oils, eg. Olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, Almond oil, palm oil, coconut oil, palm kernel oil, and the like.
Auch beliebige Abmischungen solcher Öl- und Wachskomponenten sind vorteilhaft im Sinne der vorliegenden Erfindung einzusetzen. Es kann auch gegebenenfalls vorteilhaft sein, Wachse, beispielsweise Cetylpalmitat, als alleinige Lipidkomponente der Ölphase einzusetzen.Any mixtures of such oil and wax components are advantageous in Use of the present invention. It may also be advantageous if necessary waxes, for example cetyl palmitate, as the sole lipid component of the oil phase use.
Vorteilhaft wird die Ölphase gewählt aus der Gruppe 2-Ethylhexylisostearat, Octyldode canol, Isotridecylisononanoat, Isoeicosan, 2-Ethylhexylcocoat, C12-15-Alkylbenzoat, Capryl-Caprinsäure-triglycerid, Dicaprylylether.Advantageously, the oil phase is selected from the group consisting of 2-ethylhexyl isostearate, octyldodecanol, isotridecyl isononanoate, isoeicosane, 2-ethylhexyl cocoate, C 12-15 alkyl benzoate, caprylic capric acid triglyceride, dicaprylyl ether.
Besonders vorteilhaft sind Mischungen aus C12-15-Alkybenzoat und 2-Ethylhexylisostea rat, Mischungen aus C12-15-Alkybenzoat und Isotridecylisononanoat sowie Mischungen aus C12-15-Alkybenzoat, 2-Ethylhexylisostearat und Isotridecylisononanoat.Particularly advantageous are mixtures of C 12-15 -alkyl benzoate and 2-Ethylhexylisostea rat, mixtures of C 12-15 -alkyl benzoate and Isotridecylisononanoat and mixtures of C 12-15 -alkyl benzoate, 2-Ethylhexylisostearat and Isotridecylisononanoat.
Von den Kohlenwasserstoffen sind Paraffinöl, Squalan und Squalen vorteilhaft im Sinne der vorliegenden Erfindung zu verwenden.Of the hydrocarbons, paraffin oil, squalane and squalene are advantageous in the sense to use the present invention.
Vorteilhaft kann die Ölphase ferner einen Gehalt an cyclischen oder linearen Silikonölen aufweisen oder vollständig aus solchen Ölen bestehen, wobei allerdings bevorzugt wird, außer dem Silikonöl oder den Silikonölen einen zusätzlichen Gehalt an anderen Ölpha senkomponenten zu verwenden.Advantageously, the oil phase may further contain cyclic or linear silicone oils or consist entirely of such oils, although it is preferred that in addition to the silicone oil or the silicone oils an additional content of other oil phase vertical components to use.
Vorteilhaft wird Cyclomethicon (Octamethylcyclotetrasiloxan) als erfindungsgemäß zu verwendendes Silikonöl eingesetzt. Aber auch andere Silikonöle sind vorteilhaft im Sin ne der vorliegenden Erfindung zu verwenden, beispielsweise Hexamethylcyclotrisiloxan, Polydimethylsiloxan, Poly(methylphenylsiloxan).Advantageously, cyclomethicone (octamethylcyclotetrasiloxane) is used as the invention used silicone oil. But other silicone oils are beneficial in Sin ne of the present invention, for example hexamethylcyclotrisiloxane, Polydimethylsiloxane, poly (methylphenylsiloxane).
Besonders vorteilhaft sind ferner Mischungen aus Cyclomethicon und Isotridecylisono nanoat, aus Cyclomethicon und 2-Ethylhexylisostearat.Also particularly advantageous are mixtures of cyclomethicone and isotridecylisono nanoate, from cyclomethicone and 2-ethylhexyl isostearate.
Die wäßrige Phase der erfindungsgemäßen Zubereitungen enthält gegebenenfalls vor
teilhaft
The aqueous phase of the preparations according to the invention may contain some geous
- - Alkohole, Diole oder Polyole niedriger C-Zahl, sowie deren Ether, vorzugsweise Ethanol, Isopropanol, Propylenglykol, Glycerin, Ethylenglykol, Ethylenglykolmo noethyl- oder -monobutylether, Propylenglykolmonomethyl, -monoethyl- oder -monobutylether, Diethylenglykolmonomethyl- oder -monoethylether und analoge Produkte, ferner Alkohole niedriger C-Zahl, z. B. Ethanol, Isopropanol, 1,2-Pro pandiol, Glycerin sowie insbesondere ein oder mehrere Verdickungsmittel, wel ches oder welche vorteilhaft gewählt werden können aus der Gruppe Siliciumdi oxid, Aluminiumsilikate, Polysaccharide bzw. deren Derivate, z. B. Hyaluronsäure, Xanthangummi, Hydroxypropylmethylcellulose, besonders vorteilhaft aus der Gruppe der Polyacrylate, bevorzugt ein Polyacrylat aus der Gruppe der soge nannten Carbopole, beispielsweise Carbopole der Typen 980, 981, 1382, 2984, 5984, jeweils einzeln oder in Kombination.- Alcohols, diols or polyols low C number, and their ethers, preferably Ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol mo noethyl or monobutyl ether, propylene glycol monomethyl, -monoethyl- or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and analogous Products, also low C-number alcohols, e.g. For example, ethanol, isopropanol, 1,2-Pro pandiol, glycerol and in particular one or more thickening agents, wel Ches or which can be advantageously selected from the group silicon di oxide, aluminum silicates, polysaccharides or their derivatives, for. Hyaluronic acid, Xanthan gum, hydroxypropylmethylcellulose, particularly advantageous from the Group of polyacrylates, preferably a polyacrylate from the group of soge named carbopols, for example carbopols of types 980, 981, 1382, 2984, 5984, each individually or in combination.
Die kosmetischen oder dermatologischen Lichtschutzzubereitungen enthalten vorteilhaft anorganische Pigmente, insbesondere Mikropigmente, z. B. in Mengen von 0,1 Gew.-% bis 30 Gew.-%, vorzugsweise in Mengen von 0,5 Gew.-% bis 10 Gew.-%, insbesondere aber 1 Gew.-% bis 6 Gew.-%, bezogen auf das Gesamtgewicht der Zubereitungen.The cosmetic or dermatological sunscreen preparations contain advantageous inorganic pigments, in particular micropigments, for. B. in amounts of 0.1 wt .-% to 30 wt .-%, preferably in amounts of 0.5 wt .-% to 10 wt .-%, in particular but 1 wt .-% to 6 wt .-%, based on the total weight of the preparations.
Es ist erfindungsgemäß vorteilhaft, außer den erfindungsgemäßen Kombinationen öllös liche UVA-Filter und/oder UVB-Filter in der Lipidphase und/oder wasserlösliche UVA- Filter und/oder UVB-Filter in der wäßrigen Phase einzusetzen. It is advantageous according to the invention, in addition to the combinations according to the invention öllös Liche UVA filters and / or UVB filters in the lipid phase and / or water-soluble UVA Use filters and / or UVB filters in the aqueous phase.
Vorteilhaft können die erfindungsgemäßen Lichtschutzformulierungen weitere Substan zen enthalten, die UV-Strahlung im UVB-Bereich absorbieren, wobei die Gesamtmenge der Filtersubstanzen z. B. 0,1 Gew.-% bis 30 Gew.-%, vorzugsweise 0,5 bis 10 Gew.-%, insbesondere 1 bis 6 Gew.-% beträgt, bezogen auf das Gesamtgewicht der Zubereitun gen, um kosmetische Zubereitungen zur Verfügung zu stellen, die die Haut vor dem gesamten Bereich der ultravioletten Strahlung schützen. Sie können auch als Sonnen schutzmittel dienen.Advantageously, the sunscreen formulations according to the invention can be further substituents containing UV radiation in the UVB range, the total amount the filter substances z. 0.1% to 30% by weight, preferably 0.5 to 10% by weight, in particular 1 to 6 wt .-%, based on the total weight of the preparation to provide cosmetic preparations that protect the skin from the skin protect entire area of ultraviolet radiation. They can also be called suns serve as a protective agent.
Die weiteren UVB-Filter können öllöslich oder wasserlöslich sein. Vorteilhafte öllösliche
UVB-Filtersubstanzen sind z. B.:
The other UVB filters may be oil-soluble or water-soluble. Advantageous oil-soluble UVB filter substances are z. B .:
- - 3-Benzylidencampher-Derivate, vorzugsweise 3-(4-Methylbenzyliden)campher, 3- Benzylidencampher;3-benzylidene camphor derivatives, preferably 3- (4-methylbenzylidene) camphor, 3 benzylidenecamphor;
- - 4-Aminobenzoesäure-Derivate, vorzugsweise 4-(Dimethylamino)-benzoesäure(2- ethylhexyl)ester, 4-(Dimethylamino)benzoesäureamylester;4-aminobenzoic acid derivatives, preferably 4- (dimethylamino) benzoic acid (2- ethylhexyl) ester, 4- (dimethylamino) benzoic acid amyl ester;
- - Ester der Zimtsäure, vorzugsweise 4-Methoxyzimtsäure(2-ethylhexyl)ester, 4- Methoxyzimtsäureisopentylester;Esters of cinnamic acid, preferably 4-methoxycinnamic acid (2-ethylhexyl) ester, 4- methoxycinnamate;
- - Derivate des Benzophenons, vorzugsweise 2-Hydroxy-4-methoxybenzophenon, 2- Hydroxy-4-methoxy-4'-methylbenzophenon, 2,2'-Dihydroxy-4-methoxybenzophenon;Derivatives of benzophenone, preferably 2-hydroxy-4-methoxybenzophenone, 2- Hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone;
- - Ester der Benzalmalonsäure, vorzugsweise 4-Methoxybenzalmalonsäuredi(2-ethylhe xyl)ester;Esters of benzalmalonic acid, preferably 4-methoxybenzalmalonic acid di (2-ethylhe xyl ester);
Vorteilhafte wasserlösliche UVB-Filtersubstanzen sind z. B.:Advantageous water-soluble UVB filter substances are z. B .:
- - Salze der 2-Phenylbenzimidazol-5-sulfonsäure wie ihr Natrium-, Kalium- oder ihr Tri ethanolammonium-Salz, sowie die Sulfonsäure selbst;Salts of 2-phenylbenzimidazole-5-sulfonic acid, such as its sodium, potassium or tri ethanolammonium salt, as well as the sulfonic acid itself;
- - Sulfonsäure-Derivate von Benzophenonen, vorzugsweise 2-Hydroxy-4-methoxyben zophenon-5-sulfonsäure und deren Salze;Sulfonic acid derivatives of benzophenones, preferably 2-hydroxy-4-methoxybenzene zophenone-5-sulfonic acid and its salts;
- - Sulfonsäure-Derivate des 3-Benzylidencamphers, wie z. B. 4-(2-Oxo-3-bornylidenme thyl)benzolsulfonsäure, 2-Methyl-5-(2-oxo-3-bomylidenmethyl)sulfonsäure und deren Salze.- Sulfonic acid derivatives of 3-Benzylidencamphers, such as. B. 4- (2-oxo-3-bornylidenme thyl) benzenesulfonic acid, 2-methyl-5- (2-oxo-3-bomylidenemethyl) sulfonic acid and their Salts.
Die Liste der genannten weiteren UVB-Filter, die in Kombination mit den erfindungsge mäßen Wirkstoffkombinationen verwendet werden können, soll selbstverständlich nicht limitierend sein. The list of said other UVB filters used in combination with the erfindungsge Of course, active ingredient combinations can be used, of course not be limiting.
Es kann auch von Vorteil sein, die erfindungsgemäßen Kombinationen mit weiteren UVA-Filtern zu kombinieren, die bisher üblicherweise in kosmetischen Zubereitungen enthalten sind. Bei diesen Substanzen handelt es sich vorzugsweise um Derivate des Dibenzoylmethans, insbesondere um 1-(4'-tert.Butylphenyl)-3-(4'-methoxyphenyl)pro pan-1,3-dion und um 1-Phenyl-3-(4'-isopropylphenyl)propan-1,3-dion. Auch diese Kom binationen bzw. Zubereitungen, die diese Kombinationen enthalten, sind Gegenstand der Erfindung. Es können die für die UVB-Kombination verwendeten Mengen eingesetzt werden.It may also be advantageous to use the combinations according to the invention with others To combine UVA filters, which have traditionally been used in cosmetic preparations are included. These substances are preferably derivatives of Dibenzoylmethane, in particular 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) pro pan-1,3-dione and 1-phenyl-3- (4'-isopropylphenyl) propane-1,3-dione. Also this comm combinations or preparations containing these combinations are subject matter the invention. The quantities used for the UVB combination can be used become.
Ferner ist vorteilhaft, die erfindungsgemäßen Wirkstoffkombinationen mit weiteren UVA und/oder UVB-Filtern zu kombinieren.Furthermore, it is advantageous to use the active compound combinations according to the invention with further UVA and / or UVB filters.
Es ist auch besonders vorteilhaft, die erfindungsgemäßen Wirkstoffkombinationen mit
Salicylsäurederivaten zu kombinieren, von denen einige Vertreter bekannt sind, welche
ebenfalls UV-Strahlung absorbieren können. Zu gebräuchlichen UV-Filtern gehören
It is also particularly advantageous to combine the active compound combinations according to the invention with salicylic acid derivatives, some of which are known which can likewise absorb UV radiation. To common UV filters belong
Gegenstand der Erfindung ist auch ein Verfahren zur Herstellung der erfindungsgemä ßen kosmetischen und/oder dermatologischen Lichtschutzzubereitungen, das dadurch gekennzeichnet ist, daß man in an sich bekannter Weise den 4,4',4''-(1,3,5-Triazin- 2,4,6-triyltriimino)-tris-benzoesäure-tris(2-ethylhexylester) in einem oder mehreren erfin dungsgemäß verwendeten Guerbet-Alkoholen oder einer Ölphase mit einem Gehalt an erfindungsgemäß verwendeten Guerbet-Alkoholen bei gleichmäßigem Rühren und ge gebenenfalls unter Erwärmen suspendiert und gewünschtenfalls homogenisiert, gege benenfalls mit weiteren Lipidkomponenten und gegebenenfalls mit einem oder mehreren Emulgatoren vereinigt, hernach die Ölphase mit der wäßrigen Phase, in welche gegebe nenfalls ein Verdickungsmittel eingearbeitet worden ist, und welche vorzugsweise etwa die gleiche Temperatur besitzt wie die Ölphase, vermischt, gewünschtenfalls homogeni siert und auf Raumtemperatur abkühlen läßt. Nach Abkühlen auf Raumtemperatur kann, insbesondere, wenn noch flüchtige Bestandteile eingearbeitet werden sollen, nochma liges Homogenisieren erfolgen.The invention also provides a process for the preparation of the novel process cosmetic and / or dermatological sunscreens characterized in that in a conventional manner the 4,4 ', 4' '- (1,3,5-triazine) 2,4,6-triyltriimino) tris-benzoic acid tris (2-ethylhexyl ester) in one or more of the same Guerbet alcohols used according to the invention or an oil phase containing Guerbet alcohols used in the invention with uniform stirring and ge if appropriate suspended with heating and, if desired, homogenized, if appropriate with further lipid components and optionally with one or more Emulsifiers combined, then the oil phase with the aqueous phase, in which give If necessary, a thickener has been incorporated, and which preferably about the same temperature as the oil phase, mixed, if desired homogenei and allowed to cool to room temperature. After cooling to room temperature, in particular, if still volatile components are to be incorporated, nochma Homogeneous done.
Die nachfolgenden Beispiele sollen die vorliegende Erfindung verdeutlichen, ohne sie einzuschränken. Alle Mengenangaben, Anteile und Prozentanteile sind, soweit nicht anders angegeben, auf das Gewicht und die Gesamtmenge bzw. auf das Gesamtge wicht der Zubereitungen bezogen. The following examples are intended to illustrate the present invention without it limit. All quantities, percentages and percentages are, if not otherwise indicated, on the weight and the total amount or on the total amount weight of the preparations.
Claims (6)
wobei R1 und R2 unverzweigte Alkylreste mit 2 bis 18 Kohlenstoffatomen bedeuten.1. Sunscreen active combination of 4,4 ', 4''- (1,3,5-triazine-2,4,6-triyltriimi no) tris-benzoic acid tris (2-ethylhexylester) and Guerbet alcohols of the structure
where R 1 and R 2 are unbranched alkyl radicals having 2 to 18 carbon atoms.
wobei R1 und R2 unverzweigte Alkylreste mit 2 bis 18 Kohlenstoffatomen bedeuten als Lösungsmittel, Lösungsvermittler oder Solubilisator für 4,4',4''-(1,3,5-Triazin-2,4,6-triyltri imino)-tris-benzoesäure-tris(2-ethylhexylester), insbesondere für die Verwendung in Lichtschutzmitteln.2. Use of guerbet alcohols of the structure
where R 1 and R 2 are unbranched alkyl radicals having 2 to 18 carbon atoms as solvent, solubilizer or solubilizer for 4,4 ', 4''- (1,3,5-triazine-2,4,6-triyltriimino) tris benzoic acid tris (2-ethylhexyl ester), in particular for use in light stabilizers.
R1 = Propyl, Butyl, Pentyl, Hexyl, Heptyl oder Octyl und
R2 = Hexyl, Heptyl, Octyl, Nonyl, Decyl, Undecyl, Dodecyl, Tridecyl oder Tetradecyl,
darstellen.5. Combinations according to claim 1 or use according to claim 2, characterized in that the one or more Guerbet alcohols are selected from the group in which
R 1 = propyl, butyl, pentyl, hexyl, heptyl or octyl and
R 2 = hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl or tetradecyl,
represent.
Priority Applications (1)
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DE1996151057 DE19651057A1 (en) | 1996-12-09 | 1996-12-09 | Stabilised light-protection composition, e.g. for cosmetic use |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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DE1996151057 DE19651057A1 (en) | 1996-12-09 | 1996-12-09 | Stabilised light-protection composition, e.g. for cosmetic use |
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DE19651057A1 true DE19651057A1 (en) | 1998-06-10 |
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Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0457687A1 (en) * | 1990-05-18 | 1991-11-21 | L'oreal | Screening cosmetic emulsion containing an UV-A screen and an UV-B screen |
EP0685223A1 (en) * | 1994-06-03 | 1995-12-06 | L'oreal | Anti-UV cosmetic compositions and uses |
-
1996
- 1996-12-09 DE DE1996151057 patent/DE19651057A1/en not_active Withdrawn
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0457687A1 (en) * | 1990-05-18 | 1991-11-21 | L'oreal | Screening cosmetic emulsion containing an UV-A screen and an UV-B screen |
EP0685223A1 (en) * | 1994-06-03 | 1995-12-06 | L'oreal | Anti-UV cosmetic compositions and uses |
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