WO2024253837A1 - Compositions d'écran solaire à faible pénétration - Google Patents

Compositions d'écran solaire à faible pénétration Download PDF

Info

Publication number
WO2024253837A1
WO2024253837A1 PCT/US2024/030473 US2024030473W WO2024253837A1 WO 2024253837 A1 WO2024253837 A1 WO 2024253837A1 US 2024030473 W US2024030473 W US 2024030473W WO 2024253837 A1 WO2024253837 A1 WO 2024253837A1
Authority
WO
WIPO (PCT)
Prior art keywords
weight percent
composition
absorbers
sunscreen composition
niacinamide
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.)
Ceased
Application number
PCT/US2024/030473
Other languages
English (en)
Other versions
WO2024253837A8 (fr
Inventor
Livea Fujita Barbosa
Susan Daly
Indaiá Lara GEHLEN
Ricardo SEGOVIA-BORRAY
Maria Carolina SEMPRINI
Cinthia SATAKE
Camilla Floriano MENDES DE OLIVEIRA
Rodrigo Collina Romanhole
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kenvue Brands LLC
Original Assignee
Kenvue Brands LLC
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from US18/653,546 external-priority patent/US20240407991A1/en
Application filed by Kenvue Brands LLC filed Critical Kenvue Brands LLC
Priority to CN202480037628.0A priority Critical patent/CN121263167A/zh
Priority to AU2024284595A priority patent/AU2024284595A1/en
Priority to EP24734552.3A priority patent/EP4724029A1/fr
Publication of WO2024253837A1 publication Critical patent/WO2024253837A1/fr
Publication of WO2024253837A8 publication Critical patent/WO2024253837A8/fr
Priority to CONC2025/0016231A priority patent/CO2025016231A2/es
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • A61K8/27—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
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/29—Titanium; 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
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • 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
    • 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
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/30—Characterized by the absence of a particular group of ingredients

Definitions

  • sunscreen compositions are commonly used to provide protection from the sun, and a variety of sunscreen compositions are commercially available. Many contain low molecular weight, organic UV absorbers such as octocrylene, homosalate, avobenzone, oxybenzone, octyl salicylate and cinnamates. While these UV filters are effective for absorbing UV radiation, high amounts are often required to provide a high SPF sunscreen composition. Because they are low molecular weight compounds, consumers are sometimes concerned about their potential to penetrate the skin, particularly when used in high amounts.
  • UV absorber combination is diethylamino hydroxybenzoyl hexyl benzoate, ethylhexyl triazone, methylene bis-benzotriazolyl tetramethylbutylphenol, tris-biphenyl triazine, and bis-ethylhexyloxyphenol methoxyphenyl triazine along with the low molecular weight UV absorber ethylhexyl methoxycinnamate.
  • LUPIN Propiacne Day Logao Hidratante com Proteqao Solar SPF 35 also contains a combination of UV absorbers with titanium dioxide.
  • the UV absorbers are diethylamino hydroxybenzoyl hexyl benzoate, tris-biphenyl triazine, bis- ethylhexyloxyphenol methoxyphenyl triazine, methylene BlS-benzotriazolyl tetramethylbutylphenol, and ethylhexyl triazone.
  • the product also contains the low molecular weight UV absorber octocrylene.
  • Sunscreen compositions substantially free of low molecular weight UV absorbers such as ethylhexyl methoxycinnamate and octocrylene, and therefore substantially non-penetrating to the skin, have now been discovered.
  • the present invention provides a sunscreen composition
  • a sunscreen composition comprising: (a) diethylamino hydroxybenzoyl hexyl benzoate; (b) bis-ethylhexyloxyphenol methoxyphenyl triazine; (c) ethylhexyl triazone; and (d) methylene bis-benzotriazolyl tetramethylbutylphenol; wherein the sunscreen composition is substantially free of UV absorbers having a molecular mass of 380 Daltons or less.
  • composition may optionally further comprise up to about 3 weight percent of tris-biphenyl triazine.
  • composition may optionally further comprise up to about 2 weight percent of a UV blocker such as titanium dioxide or zinc oxide.
  • a UV blocker such as titanium dioxide or zinc oxide.
  • composition may optionally further comprise a polymeric UV absorber, for example a linear UV-absorbing polyether comprising a covalently bound benzotriazole chromophores.
  • a polymeric UV absorber for example a linear UV-absorbing polyether comprising a covalently bound benzotriazole chromophores.
  • composition may optionally further comprise one or more cosmetically acceptable active agents, such as niacinamide, glycerin, acetyl glucosamine, and sodium hyaluronate.
  • cosmetically acceptable active agents such as niacinamide, glycerin, acetyl glucosamine, and sodium hyaluronate.
  • topically applying means directly laying on or spreading on outer skin or the scalp, e.g., by use of the hands or an applicator such as a wipe, roller, or spray.
  • cosmetic refers to a beautifying substance or preparation which preserves, restores, bestows, simulates, or enhances the appearance of bodily beauty or appears to enhance the beauty or youthfulness, specifically as it relates to the appearance of tissue or skin or hair.
  • cosmetically effective amount means an amount of a physiologically active compound or composition sufficient for treating one or more conditions, but low enough to avoid serious side effects.
  • the cosmetically effective amount of the compound or composition will vary with the condition being treated, the age and physical condition of the end user, the severity of the condition being treated/prevented, the duration of the treatment, the nature of other treatments, the specific compound or product/composition employed, the cosmetically acceptable carrier utilized, and like factors.
  • cosmetically acceptable means that the ingredients the term describes are suitable for use in contact with tissues (e.g., the skin or hair) without undue toxicity, incompatibility, instability, irritation, allergic response, or the like.
  • a “cosmetically acceptable active agent” is a compound (synthetic or natural) that has a cosmetic or therapeutic effect on the skin or hair.
  • treatment or treating refers to mitigating, reducing, preventing, improving, or eliminating the presence or signs of a condition or disorder.
  • phase-stable means the water and oil phases of an emulsion do not appreciably separate at room temperature for at least two weeks.
  • substantially free of means not intentionally or deliberately added.
  • a composition may be substantially free of an ingredient it if contains less than 1 % by weight, or less than 0.5% by weight, or less than 0.1 % by weight, of such ingredient.
  • a composition may contain none of such ingredient, i.e., 0% by weight and be completely free of such ingredient.
  • UV absorber means a compound that absorbs radiation in some portion of the ultraviolet spectrum (290nm-400nm), such as one having an extinction coefficient of at least about 1000 mol -1 cm 1 , for at least one wavelength within the above-defined ultraviolet spectrum.
  • a percentage or concentration refers to a percentage or concentration by weight (i.e. , % (W/W). Unless stated otherwise, all ranges are inclusive of the endpoints, e.g., “from 4 to 9” includes the endpoints 4 and 9.
  • the sunscreen composition of the invention comprises a combination of UV absorbers each having a molecular mass greater than 380 Daltons.
  • the sunscreen composition comprises: (a) diethylamino hydroxybenzoyl hexyl benzoate; (b) bis-ethylhexyloxyphenol methoxyphenyl triazine; (c) ethylhexyl triazone; and (d) methylene bis-benzotriazolyl tetramethylbutylphenol.
  • the combination of UV absorbers in the sunscreen composition may consist essentially of, or consist of: (a) diethylamino hydroxybenzoyl hexyl benzoate; (b) bis- ethylhexyloxyphenol methoxyphenyl triazine; (c) ethylhexyl triazone; and (d) methylene bis-benzotriazolyl tetramethylbutylphenol.
  • the sunscreen composition of the invention may comprise UV absorbers, UV blockers and a cosmetically acceptable topical carrier, wherein the UV absorbers and UV blockers consist essentially of, or consist of: (a) about 2 to about 6 weight percent of diethylamino hydroxybenzoyl hexyl benzoate; (b) 3 weight percent or less of tris-biphenyl triazine; (c) about 0.5 to about 3.5 weight percent of bis- ethylhexyloxyphenol methoxyphenyl triazine; (d) about 1 .64 to about 4.55 weight percent of ethylhexyl triazone; (e) about 2 to about 6 weight percent of methylene bis-benzotriazolyl tetramethylbutylphenol; and (f) 2 weight percent or less of titanium dioxide.
  • the sunscreen composition is substantially free of UV absorbers having a molecular mass of 380 Daltons and below.
  • the sunscreen composition is completely free of UV absorbers
  • the sunscreen composition comprises only UV absorbers having molecular masses greater than 380 Daltons. It may optionally also comprise one or more UV blockers or polymeric UV absorbers, as described below. However, it is substantially free of UV absorbers having a molecular mass of 380 Daltons or less. In this manner, the sunscreen composition is advantageously low penetrating or substantially non-penetrating to skin or hair.
  • all the UV absorbers in the sunscreen composition have melting points above 50° C.
  • the total amount of UV absorbers in the sunscreen composition ranges from about 9 to about 20 weight percent, preferably about 9.5 to about 17.5 weight percent, of the total weight of the sunscreen composition.
  • the total amount of UV absorbers in the sunscreen composition may be less than about 18 weight percent of the total weight of the sunscreen composition. More preferably, the total amount of UV absorbers in the sunscreen composition is less than about 15 weight percent of the total weight of the sunscreen composition.
  • the composition Despite the low total amount of UV absorbers in the sunscreen composition, the composition nevertheless provides high SPF values.
  • DHHB DIETHYLAMINO HYDROXYBENZOYL HEXYL BENZOATE
  • the first UV absorber in the sunscreen composition is diethylamino hydroxybenzoyl hexyl benzoate (“DHHB”).
  • Diethylamino hydroxybenzoyl hexyl benzoate is also known chemically as benzoic acid, 2-[-4-(diethylamino)-2- hydroxybenzoyl]-, hexylester. It is commercially available, for example, as UVINUL® A-PLUS from BASF or PARSOL® DHHB from DSM.
  • the molecular mass of diethylamino hydroxybenzoyl hexyl benzoate is 398 Daltons.
  • the sunscreen composition preferably contains about 2 to about 6 weight percent of diethylamino hydroxybenzoyl hexyl benzoate based on the total weight of the sunscreen composition.
  • the sunscreen composition contains about 3 to about 5.5 weight percent of diethylamino hydroxybenzoyl hexyl benzoate based on the total weight of the sunscreen composition.
  • the second UV absorber in the sunscreen composition is bisethylhexyloxyphenol methoxyphenyl triazine (“BEMT”).
  • Bis-ethylhexyloxyphenol methoxyphenyl triazine is also known chemically as phenol, 2,2'-[6-(4- methoxyphenyl)-1 ,3,5-triazine-2,4-diyl]bis(5-((2-ethylhexyl)oxy; (1 ,3,5)-triazine-2,4- bis ⁇ [4-(2-ethyl-hexyloxy)-2-hydroxy]-phenyl ⁇ -6-(4-methoxyphenyl); anisotriazine; and bemotrizinol. It is commercially available, for example, from BASF as Tinosorb® S.
  • the molecular mass of bis-ethylhexyloxyphenol methoxyphenyl triazine is 627 Daltons.
  • the sunscreen composition preferably contains about 0.5 to about 3.5 weight percent of bis-ethylhexyloxyphenol methoxyphenyl triazine based on the total weight of the sunscreen composition.
  • the sunscreen composition contains about 1 .5 to about 2.3 weight percent of bis-ethylhexyloxyphenol methoxyphenyl triazine based on the total weight of the sunscreen composition.
  • EHT ETHYLHEXYL TRIAZONE
  • the third UV absorber in the sunscreen composition is ethylhexyl triazone (“EHT”).
  • Ethylhexyl triazone is also known chemically as 4-[[4,6-bis[[4-(2- ethylhexoxy-oxomethyl)phenyl]amino]-1 ,3,5-triazin-2-yl]amino]benzoic acid 2- ethylhexyl ester; and octyl triazone. It is commercially available, for example, from BASF as UVINUL® T 150.
  • the molecular mass of ethylhexyl triazone is 823 Daltons.
  • the sunscreen composition preferably contains about 1 .64 to about 4.55 weight percent of ethylhexyl triazone based on the total weight of the sunscreen composition.
  • the fourth UV absorber in the sunscreen composition is methylene bis- benzotriazolyl tetramethylbutylphenol (“MBBT”).
  • Methylene bis-benzotriazolyl tetramethylbutylphenol is also known chemically as phenol, 2,2'-methylenebis[6-(2H- benzotriazol-2-yl)-4-(1 ,1 ,3,3-tetramethylbutyl), and bisoctrizole. It is commercially available, for example, as Tinosorb® M from BASF.
  • the molecular mass of methylene bis-benzotriazolyl tetramethylbutylphenol is 659 Daltons.
  • the sunscreen composition preferably contains about 2 to about 6 weight percent of methylene bis-benzotriazolyl tetramethylbutylphenol based on the total weight of the sunscreen composition.
  • the sunscreen composition contains about 2 to about 5.5 weight percent of methylene bis-benzotriazolyl tetramethylbutylphenol based on the total weight of the sunscreen composition.
  • TBT TRIS-BIPHENYL TRIAZINE
  • the composition may optionally contain the additional UV absorber trisbiphenyl triazine (“TBT”).
  • TBT trisbiphenyl triazine
  • Tris-biphenyl triazine is also known chemically as 1 ,3,5- Triazine, 2,4,6-tris([1 ,1'-biphenyl]-4-yl)-, and 2,4,6-tri([1 ,1 '-biphenyl]-4-yl)-1 ,3,5- triazine. It is commercially available as Tinosorb® A2B from BASF.
  • the molecular mass of tris-biphenyl triazine is 537 Daltons.
  • the sunscreen composition preferably contains 3 weight percent or less of tris-biphenyl triazine based on the total weight of the sunscreen composition. [0044] More preferably the sunscreen composition contains about 0.5 to about 1 weight percent of tris-biphenyl triazine based on the total weight of the sunscreen composition.
  • the sunscreen composition is substantially free, preferably completely free of UV absorbers having a molecular mass of 380 Daltons or less.
  • UV absorbers having a molecular mass of 380 Daltons or less include: octocrylene, homosalate, avobenzone, octyl salicylate, methoxycinnamate derivatives such as octyl methoxycinnamate and isoamyl methoxycinnamate; camphor derivatives such as 4-methyl benzylidene camphor, camphor benzalkonium methosulfate, ecamsule (Mexoryl® SX); terephthalylidene dicamphor sulfonic acid, and terephthalylidene dicamphor sulfonic acid; other salicylate derivatives such as trolamine salicylate and ethylhexyl salicylate; sulfonic acid derivatives such as phenylbenzimidazole sulfonic acid; benzone derivatives such as dioxybenzone, sulisobenzone, and oxy
  • the sunscreen composition is substantially free of UV absorbers having a melting point under 30° C.
  • the sunscreen composition may be free of octocrylene.
  • the sunscreen composition may be free of homosalate.
  • the sunscreen composition may be free of avobenzone.
  • the sunscreen composition may be free of octyl salicylate.
  • the sunscreen composition may be free of ethylhexyl methoxycinnamate.
  • the sunscreen composition may be free of phenylbenzimidazole sulfonic acid.
  • the sunscreen composition may optionally contain a UV blocker.
  • UV blocker means a compound that reflects or scatters UV radiation.
  • UV blockers are typically inorganic metallic oxides, including titanium dioxide, zinc oxide, and other transition metal oxides. They are typically solid particles in a micronized or nanonized form having a diameter from about 0.01 micron to about 10 microns.
  • the sunscreen composition may contain 2 weight percent or less of a UV blocker based on the total weight of the sunscreen composition.
  • the UV blocker may be selected from the group consisting of titanium dioxide and zinc oxide.
  • the UV blocker may be titanium dioxide.
  • An example of a titanium dioxide that may be used is Titanium Dioxide (and) Silica, commercially available from Merck as Eusolex® T AVO.
  • the sunscreen composition may also optionally comprise a polymeric UV absorber.
  • the polymeric UV absorber may be a linear UV absorbing polyether, i.e., a polymer comprising a backbone of ether functional groups and UV absorbing chromophores covalently bound to the backbone.
  • linear UV absorbing polyether means a polyether that absorbs radiation in some portion of the ultraviolet spectrum (wavelengths between 290 and 400 nm).
  • the linear UV absorbing polyether has a weight average molecular weight (Mw), which may be suitable for reducing or preventing the chromophore from absorbing through the skin.
  • Mw weight average molecular weight
  • a suitable molecular weight for the linear UV absorbing polyether is Mw greater than 500.
  • Mw is in the range of about 500 to about 50,000.
  • the Mw is in the range of about 1 ,000 to about 20,000, such as from about 1 ,000 to about 10,000.
  • Such linear UV absorbing polyethers are typically contained in polymer compositions composed of a complex combination of different molecules, i.e., a complex reaction product. Typically, these polymer compositions comprise at least about 50% or more of the linear UV-absorbing polyether. The polymer compositions may comprise at least about 75% of the linear UV-absorbing polyether. The polymer compositions may comprise at least about 90% of the linear UV-absorbing polyether, such as about 95% or more.
  • Linear UV absorbing polyethers include a plurality of ether functional groups covalently bonded to each other.
  • the “backbone” of the linear UV absorbing polyether refers to the longest continuous sequence of covalently bonded ether functional groups. Other smaller groups of covalently bonded atoms are considered pendant groups that branch from the backbone.
  • the linear UV absorbing polyether preferably has a backbone that is unbranched.
  • the linear UV absorbing polyether may include glyceryl repeat units and accordingly, may be characterized as a polyglycerol.
  • glyceryl repeat units also referred to herein “glyceryl remnant units” means glycerol units excluding nucleophilic groups such as hydroxyl groups.
  • Glyceryl remnant units include ether functional groups, and generally may be represented as C3H5O for linear and dendritic remnants (Rokicki et al. Green Chemistry., 2005, 7, 52).
  • Suitable glyceryl remnant units include dehydrated forms (i.e. one mole of water removed) of the following glyceryl units: linear-1 ,4 (L1 ,4) glyceryl units; linear-1 ,3 (L1 ,3) glyceryl repeat units; dendritic (D) glyceryl units; terminal-1 ,2 (T 1 ,2) units; and terminal-1 ,3 (T 1 ,3) units.
  • the linear UV-absorbing polyether includes either or both of the repeat units shown in FORMULA IA and FORMULA IB, below:
  • X may be selected from, for example, hydrogen, linear alkyl, alkenyl or alkynyl hydrocarbon chains, linear siloxanes, and the like. In one embodiment the group X represents octadecane.
  • Y represents a UV-chromophore, described further below.
  • the proportion of ether repeat units bearing substituent Y is a real number expressed by Equation 1 : m/(n+m) Equation 1 where m and n each represent a real number between 0 and 1 , and the sum of n and m equals 1 .
  • the linear UV-absorbing polyether may for example be a homopolymer or a copolymer optionally containing additional pendant groups other than the UV absorbing chromophore.
  • the distribution of the pendant groups along the polymer chain can be modified to obtain optimal polymer properties.
  • the linear UV-absorbing polyether is a random copolymer, and the pendant groups including the UV absorbing chromophore are statistically distributed along the polymer chain.
  • the linear UV-absorbing polyether is a block copolymer, consisting of alternating segments of polymer backbone functionalized with a greater proportion of pendant groups.
  • the distribution of the pendant groups along the polymer backbone is somewhere between the boundary conditions of block and statistically random copolymers.
  • the linear UV absorbing polyether comprises one or more covalently bonded UV-chromophores.
  • UV-chromophores that absorb UVA radiation or UVB radiation are suitable.
  • the UV-chromophore may absorb in both the UVA and UVB region.
  • Suitable UV-chromophores include triazoles (a moiety containing a fivemembered heterocyclic ring with two carbon and three nitrogen atoms), such as benzotriazoles including hydroxyphenyl-benzotriazoles, and triazines (a six membered heterocycle containing three nitrogen and three carbon atoms).
  • examples of other UV-chromophores include camphors such as benzylidene camphor and its derivatives (such as terephthalylidene dicamphor sulfonic acid) and dibenzoylmethanes and their derivatives.
  • the UV chromophore is a benzotriazole providing both photostability and strong UVA absorbance with a structure represented in FORMULA II:
  • each R14 is independently selected from the group consisting of hydrogen, C1 -C20 alkyl, alkoxy, acyl, alkyloxy, alkylamino, and halogen;
  • R15 is independently selected from the group consisting of hydrogen, C1 -C20 alkyl, alkoxy, acyl, alkyloxy, and alkylamino,
  • R21 is selected from C1 -C20 alkyl, alkoxy, acyl, alkyloxy, and alkylamino.
  • Either of the R15 or R21 groups may include functional groups that allow attachment to a polymer.
  • the benzotriazole is derived from a transesterification product of 3-(3-(2H-benzo[d][1 ,2,3]triazol-2-yl)-5-(tert-butyl)-4-hydroxyphenyl) propanoic acid with polyethylene glycol 300, commercially available as TINUVIN 213 from BASF.
  • the benzotriazole is benzenepropanoic acid, 3- (2H-benzotriazol-2-yl)-5-(1 , 1 -dimethylethyl)-4-hydroxy-, C7-9-branched and linear alkyl esters, commercially available as TINUVIN 99 from BASF.
  • the UV-absorbing group contains a triazine moiety.
  • An exemplary triazine is 6-octyl-2-(4-(4,6-di([1 ,1 '-biphenyl]-4-yl)-1 ,3,5-triazin-2-yl)-3- hydroxyphenoxy) propanoate, commercially available as TINUVIN 479 from BASF.
  • UVB-absorbing chromophores examples include 4-aminobenzoic acid and alkane esters thereof; anthranilic acid and alkane esters thereof; salicylic acid and alkane esters thereof; hydroxycinnamic acid alkane esters thereof; dihydroxy , dicarboxy , and hydroxycarboxybenzophenones and alkane ester or acid halide derivatives thereof; dihydroxy , dicarboxy , and hydroxycarboxychalcones and alkane ester or acid halide derivatives thereof; dihydroxy , dicarboxy , and hydroxycarboxycoumarins and alkane ester or acid halide derivatives thereof; benzalmalonate (benzylidene malonate); benzimidazole derivatives (such as phenyl benzilimazole sulfonic acid, PBSA), benzoxazole derivatives, and other suitably functionalized species capable of copolymerization within the polymer chain.
  • PBSA
  • the linear UV-absorbing polyether may include more than one UV- chromophore or more than one type or chemical class of UV-chromophore.
  • the linear UV absorbing polyether preferably has a low polydispersity.
  • the polydispersity index of the linear UV absorbing polyether may be about 1 .5 or less, such as about 1 .2 or less.
  • Polydispersity index is defined as Mw/Mn (i.e. , the ratio of weight average molecular weight, Mw, to number average molecular weight, Mn).
  • Linear UV absorbing polyethers may be made as described in US9255180 and US9248092, the disclosures of which are incorporated in their entirety herein.
  • a preferred linear UV absorbing polyether is a linear UV absorbing polyether comprising benzotriazole chromophores having the following formula:
  • n and m independently from each other, are each a number from 0 to 20; and wherein at least one of m and n is > 1 .
  • the sum of n and m is a number from 3 to 10.
  • linear UV absorbing polyether comprising benzotriazole chromophores
  • such linear UV absorbing polyether comprising benzotriazole chromophores may be based on a polyglycerol backbone containing 5 glycerol units as shown in Formula IV:
  • the glycerol backbone in these preferred polyethers typically consists mainly of 3 to 10 glycerol units, whereby the hydroxyl groups of the glycerol backbone are covalently linked to the benzotriazole UV chromophore. It might be reasonably assumed that primary hydroxyl groups (terminal units) react faster than secondary hydroxyl groups, which are less reactive for derivatization. Therefore, some secondary hydroxyl groups remain unreacted.
  • the glycerol backbone consists of primarily linear and unbranched structure units. Branched isomers and higher molecular fractions including more than 10 glycerol units can be present.
  • a particularly preferred linear UV absorbing polyether is polyglyceryl benzotriazolyl t-butylhydroxyphenylpropionate.
  • Polymer compositions comprising these preferred linear UV absorbing polyethers comprising benzotriazole chromophores may further be characterized as follows:
  • These preferred linear UV-absorbing polyethers comprising benzotriazole chromophores may be prepared by esterification / transesterification reaction, including the steps of reacting a polyglycerol intermediate with a benzotriazole UV- chromophore comprising a complementary functional group to form the polyether, as described in US10596087, the disclosure of which is incorporated in its entirety herein.
  • the sunscreen composition may contain about 5 to about 20 weight percent, or about 10 to about 15 weight percent, of such a linear UV-absorbing polyether based on the total weight of the sunscreen composition.
  • Sun protection factor (SPF) of the composition may be tested using the following IN VITRO SPF TEST METHOD.
  • the baseline transmission a collagen matrix substrate (in vitro skin® - IMS - Florida Skincare Testing, Florida USA) is measured for UV absorbance using a calibrated transmission spectrophotometer with integration sphere (Labsphere® UV-1000S UV transmission analyzer, Labsphere® UV-2000S UV transmission analyzer (Labsphere, North Sutton, N.H., USA) or equivalent).
  • a test sample is then applied to the substrate using an application density of about 0.75 mg/cm2, followed by rubbing it into a uniform thin layer with a metallic pointe.
  • the sample is allowed to dry for 15 minutes and then measured for UV absorbance in the same way.
  • the absorbance measures are used to calculate SPF as known in the art using the following equation: in which:
  • the sunscreen composition advantageously has a high ratio of SPF to total amount of UV absorbers and UV blockers.
  • the ratio of the SPF of the composition to the total, combined weight percent of UV absorbers and UV blockers in the composition is at least about 4.1 , preferably at least about 4.4.
  • the sunscreen composition may have an SPF of at least about 30 as measured by the IN VITRO SPF TEST METHOD wherein the ratio of the SPF of the composition to the total, combined weight percent of UV absorbers and UV blockers in the composition is at least about 4.1 .
  • the sunscreen composition can be used by topically applying to a mammal, e.g., by the direct laying on, wiping or spreading of the composition on the skin, hair, or nails of a mammal, particularly a human.
  • the sunscreen composition preferably comprises a cosmetically acceptable topical carrier.
  • the composition is in the form of an oil-in-water emulsion containing a continuous water phase and a discontinuous oil phase dispersed within the continuous water phase.
  • other product forms may be employed, such as oil-in-water, oil-water-oil, water-oil-water, or PIT emulsions, microemulsions, anhydrous compositions, gels, oils, creams, milks, lotions, powders, lacquers, tablets, make-up or other color cosmetics, sticks, sprays and aerosols (with or without propellants), foams, pastes, preparations for hair treatment such as shampoos, conditioners, hair-care preparations, e.g., pretreatment preparations, hair tonics, styling creams, styling gels, pomades, hair rinses, treatment packs, intensive hair treatments, hair-straightening preparations, liquid hair-setting preparations, hair foams and hairsprays.
  • the sunscreen composition may be prepared using mixing and blending methodology well known in the sunscreen and cosmetic arts.
  • the sunscreen composition is an oil-in-water emulsion produced by preparing an oil phase by mixing the UV absorbers with optional oil soluble or oil-miscible ingredients; and preparing a water phase, by mixing water and optional water- soluble or water-miscible ingredients. The oil phase and the water phase may then be mixed in a manner sufficient to disperse the oil phase substantially homogeneously in the water phase such that the water phase is continuous and the oil phase discontinuous.
  • the sunscreen composition is an oil-in water emulsion that is phase stable.
  • the UV absorbers are dissolved, as opposed to being dispersed or suspended, within the oil phase.
  • Suitable solvents for the UV absorbers include dicaprylyl carbonate available as CETIOL CC from BASF.
  • the oil phase may be such that it is present in discrete droplets or units having an average diameter of about one micron to about 1000 microns, such as from about 1 micron to about 100 microns.
  • the percentage by weight of water phase in the composition may range from about 45% to about 90%, such as from about 55% to about 80%, such as from about 60% to about 80%.
  • the percentage by weight of water in the water phase may be about 90% or more, such as about 95% or more.
  • the percentage by weight of oil phase in the composition is from about 10% to about 55%, such as from about 20% to about 45%, such as from about 20% to about 40%.
  • the oil phase consists essentially of the UV absorbers.
  • the oil phase contains about 60% or more by weight of the UV absorbers, such as greater than 75% by weight of the UV absorbers, such as greater than 90% by weight of the UV absorbers, such as greater than 97% by weight of the UV absorbers, such as greater than 99% by weight of the UV absorbers.
  • composition may be combined with a "cosmetically acceptable topical carrier,” i.e. , a carrier for topical use capable of containing the other ingredients dispersed or dissolved therein and possessing acceptable properties rendering it safe to use topically.
  • a "cosmetically acceptable topical carrier” i.e. , a carrier for topical use capable of containing the other ingredients dispersed or dissolved therein and possessing acceptable properties rendering it safe to use topically.
  • the composition may optionally comprise a wide variety of additional oilsoluble materials and/or water-soluble materials conventionally used in compositions for use on skin or hair, at their art-established levels.
  • additional oilsoluble materials and/or water-soluble materials conventionally used in compositions for use on skin or hair, at their art-established levels.
  • emulsifiers for example, emulsifiers, surfactants, pearlescent or opacifying agents, thickeners, emollients, conditioners, humectants, chelating agents, exfoliants, and additives that enhance the appearance, feel, or fragrance of the cleansing composition, such as colorants, fragrances, preservatives, pH adjusting agents, and the like, can be included.
  • Water soluble or water dispersible polymers may be added to the compositions.
  • Water dispersible polymers are comprised of a water-insoluble polymer that is typically micronized and dispersed into a water carrier, possibly with the use of a surface active dispersing aid.
  • the water dispersible polymers are capable of forming a film and improving water resistance of the compositions.
  • Examples of water soluble polymers include Polyaldo® 10-1 -L (Polyglyceryl-10 Laurate), available from Lonza.
  • water dispersible polymers examples include water dispersible polyurethanes, such as Baycusan® C1000 (Polyurethane-34), available from Bayer, Dow Corning® 2501 (Bis-PEG-18 Methyl Ether Dimethyl Silane), available from Dow Corning, Eastman AQTM 38S (Polyester-5), available from Eastman Chemical, and Intelimer® 8600 (C8-22 Alkyl Acrylates/Methacrylic Acid Crosspolymer) available from Air Products.
  • water dispersible polyurethanes such as Baycusan® C1000 (Polyurethane-34), available from Bayer, Dow Corning® 2501 (Bis-PEG-18 Methyl Ether Dimethyl Silane), available from Dow Corning, Eastman AQTM 38S (Polyester-5), available from Eastman Chemical, and Intelimer® 8600 (C8-22 Alkyl Acrylates/Methacrylic Acid Crosspolymer) available from Air Products.
  • the sunscreen composition may also comprise a film former.
  • Film formers are typically hydrophobic materials that impart film forming and/or waterproofing characteristics.
  • One such agent is polyethylene, which is available from New Phase Technologies as Performalene® 400, a polyethylene having a molecular weight of 400.
  • Another suitable film former is polyethylene 2000 (molecular weight of 2000), which is available from New Phase Technologies as Performalene®.
  • Another suitable film former is synthetic wax, also available from New Phase Technologies as Performa® V-825.
  • film-formers include acrylates/acrylamide copolymer, acrylates copolymer, acrylates/C12-C22 alkylmethacrylate copolymer, polyethylene, waxes, VP/dimethiconylacrylate/polycarbamylpolyglycol ester, butylated PVP, PVP/hexadecene copolymer, octadecene/MA copolymer, PVP/eicosene copolymer, tricontanyl PVP, Brassica Campestris/Aleuritis Fordi Oil copolymer, decamethyl cyclopentasiloxane (and) trimethylsiloxysilicate, Dimethicone; Acrylates/Dimethicone Copolymer, hydrolyzed jojoba esters; jojoba esters and mixtures thereof.
  • the film former is acrylates/C12-C22 alkylmethacrylate copolymer sold under the tradename AllianzTM OPT by Ashland.
  • the film former is selected from the group consisting of hydrolyzed jojoba esters, jojoba esters, triacontanyl PVP, acrylates/dimethicone copolymer, and mixtures thereof.
  • Suitable emollients include mineral oils, petrolatum, vegetable oils (e.g., triglycerides such as caprylic/capric triglyceride), waxes and other mixtures of fatty esters, including but not limited to isopropyl palmitate, isopropyl myristate, diisopropyl adipate, dicaprylyl carbonate, C12-15 alkyl benzoate, diisopropyl sebacate, isononyl isononanoate and silicone oils such as dimethicone.
  • vegetable oils e.g., triglycerides such as caprylic/capric triglyceride
  • waxes and other mixtures of fatty esters including but not limited to isopropyl palmitate, isopropyl myristate, diisopropyl adipate, dicaprylyl carbonate, C12-15 alkyl benzoate, diisopropyl sebacate, isononyl is
  • the emollients are selected from the group consisting of C12-15 alkyl benzoate, diisopropyl adipate, diisopropyl sebacate, isopropyl palmitate and isononyl isononanoate, and mixtures thereof.
  • mixtures of triglycerides e.g., caprylic/capric triclycerides
  • esters of glycols may be used to solubilize the UV absorbers.
  • the compositions are substantially free of, or free of, emollients.
  • solvents include propylene glycol, polyethylene glycol, polypropylene glycol, glycerol, 1 ,2,4-butanetriol, sorbitol esters, 1 ,2,6- hexanetriol, ethanol, and mixtures thereof.
  • the composition may comprise an emulsifier.
  • the emulsifier is selected from the group consisting of glyceryl stearate; PEG-100 stearate, cetyl alcohol; PEG-75 stearate; ceteth-20; steareth-20, potassium cetyl phosphate, and mixtures thereof.
  • the composition includes a pigment suitable for providing color or hiding power.
  • the pigment may be one suitable for use in a color cosmetic product, including compositions for application to the hair, nails and/or skin, especially the face.
  • Color cosmetic compositions include, but are not limited to, foundations, concealers, primers, blush, mascara, eyeshadow, eyeliner, lipstick, nail polish and tinted moisturizers.
  • the pigment suitable for providing color or hiding power may be composed of iron oxides, including red and yellow iron oxides, titanium dioxide, ultramarine and chromium or chromium hydroxide colors, and mixtures thereof.
  • the pigment may be a lake pigment, e.g., an organic dye such as azo, indigoid, triphenylmethane, anthraquinone, and xanthine dyes that are designated as D&C and FD&C blues, browns, greens, oranges, reds, yellows, etc., precipitated onto inert binders such as insoluble salts.
  • lake pigments include Red #6, Red #7, Yellow #5, Violet #2 and Blue #1 .
  • the pigment may be an interference pigment.
  • interference pigments include those containing mica substrates, bismuth oxycloride substrates, and silica substrates, for instance mica/bismuth oxychloride/iron oxide pigments commercially available as CHROMALITE pigments (BASF), titanium dioxide and/or iron oxides coated onto mica such as commercially available FLAMENCO pigments (BASF), mica/titanium dioxide/iron oxide pigments including commercially available KTZ pigments (Kobo products), CELLINI pearl pigments (BASF), and borosilicate-containing pigments such as REFLECKS pigments (BASF).
  • BASF commercially available FLAMENCO pigments
  • mica/titanium dioxide/iron oxide pigments including commercially available KTZ pigments (Kobo products), CELLINI pearl pigments (BASF), and borosilicate-containing pigments such as REFLECKS pigments (BASF).
  • the sunscreen composition may include one or more compounds suitable for enhancing the photostability of the UV absorbers or other ingredients in the composition.
  • Photostabilizers include, for example, diesters or polyesters of a naphthalene dicarboxylic acid.
  • the sunscreen composition comprises a humectant.
  • humectants include, without limitation to, glycerin, pentylene glycol, butylene glycol.
  • the sunscreen composition comprises a humectant selected from the group consisting of glycerin, pentylene glycol, and mixtures thereof.
  • the sunscreen composition may advantageously comprise about 0.5 to about 2 weight percent glycerin.
  • the sunscreen composition may comprise for example about 1 weight percent of glycerin.
  • the sunscreen composition has a pH of about 5 to about 6.
  • the sunscreen composition may have a pH of about 5.5.
  • composition may comprise one or more other cosmetically acceptable active agents include for example anti-acne agents, shine control agents, antimicrobial agents, anti-inflammatory agents, anti-mycotic agents, anti-parasite agents, external analgesics, sunscreens, photoprotectors, antioxidants, keratolytic agents, surfactants, moisturizers, nutrients, vitamins, energy enhancers, anti-perspiration agents, astringents, deodorants, firming agents, anti-callous agents, and agents for skin or hair conditioning.
  • cosmetically acceptable active agents include for example anti-acne agents, shine control agents, antimicrobial agents, anti-inflammatory agents, anti-mycotic agents, anti-parasite agents, external analgesics, sunscreens, photoprotectors, antioxidants, keratolytic agents, surfactants, moisturizers, nutrients, vitamins, energy enhancers, anti-perspiration agents, astringents, deodorants, firming agents, anti-callous agents, and agents for skin or hair conditioning.
  • the amount of other cosmetically active agent in may range from about 0.001% to about 20% by weight of the composition, e.g., about 0.005% to about 10% by weight of the composition, such as about 0.01% to about 5% by weight of the composition.
  • the cosmetically acceptable active agent may be selected for instance from benzoyl peroxide, D-panthenol carotenoids, ceramides, polyunsaturated fatty acids, essential fatty acids, enzymes such as laccase, enzyme inhibitors, minerals, hormones such as estrogens, steroids such as hydrocortisone, 2- dimethylaminoethanol, copper salts such as copper chloride, peptides like argireline, syn-ake, those containing copper, and acetyl dipeptide-31 amide, coenzyme Q10, amino acids such as proline, vitamins, lactobionic acid, acetyl-coenzyme A, niacin, riboflavin, thiamin, ribose, electron transporters such as NADH and FADH2, natural extracts such as from aloe vera, feverfew, oatmeal, dill, blackberry, princess tree, Picia anomala, and chicory, resorcinols such as 4-hex
  • composition may advantageously comprise about 0.5 to about 2 weight percent of feverfew extract, for example about 1 weight percent of feverfew extract.
  • composition may advantageously comprise about 2 to about 6 weight percent of acetyl glucosamine, for example about 4 weight percent of acetyl glucosamine.
  • composition may advantageously comprise about 0.01 to about 0.1 weight percent of sodium hyaluronate, for example about 0.05 weight percent of sodium hyaluronate.
  • vitamins include, but are not limited to, vitamin A, vitamin B’s such as vitamin B3, vitamin B5, and vitamin B12, vitamin C, vitamin K, and different forms of vitamin E like alpha, beta, gamma or delta tocopherols or their mixtures, and derivatives thereof.
  • the composition may advantageously comprise about 1 to about 5 weight percent of niacinamide, for example about 2 weight percent of niacinamide.
  • antioxidants include, but are not limited to, water-soluble antioxidants such as sulfhydryl compounds and their derivatives (e.g., sodium metabisulfite and N-acetyl-cysteine), lipoic acid and dihydrolipoic acid, resveratrol, lactoferrin, and ascorbic acid and ascorbic acid derivatives (e.g., ascorbyl palmitate, ascorbyl polypeptide, and sodium ascorbyl phosphate).
  • water-soluble antioxidants such as sulfhydryl compounds and their derivatives (e.g., sodium metabisulfite and N-acetyl-cysteine), lipoic acid and dihydrolipoic acid, resveratrol, lactoferrin, and ascorbic acid and ascorbic acid derivatives (e.g., ascorbyl palmitate, ascorbyl polypeptide, and sodium ascorbyl phosphate).
  • Oil-soluble antioxidants suitable for use in the compositions of this invention include, but are not limited to, butylated hydroxytoluene, retinoids (e.g., retinol and retinyl palmitate), tocopherols (e.g., tocopherol acetate), tocotrienols, and ubiquinone.
  • Natural extracts containing antioxidants suitable for use in the compositions of this invention include, but not limited to, extracts containing flavonoids and isoflavonoids and their derivatives (e.g., genistein and diadzein), extracts containing resveratrol, rutin, and the like. Examples of such natural extracts include grape seed, green tea, pine bark, and propolis.
  • composition may comprise about 0.1 to about 0.5 weight percent of tocopherol acetate, for example about 0.2 weight percent of tocopherol acetate.
  • composition may comprise about 0.1 to about 0.5 weight percent of sodium ascorbyl phosphate, for example about 0.2 weight percent of sodium ascorbyl phosphate.
  • the composition may comprise a cosmetically acceptable active agent selected from the group consisting of niacinamide, tocopheryl acetate, sodium ascorbyl phosphate, acetyl glucosamine, trehalose, feverfew extract, glycerin, sodium hyaluronate and capryloyl glycine (and) sarcosine (and) cinnamomum seylanicum bark extract, and mixtures thereof.
  • a cosmetically acceptable active agent selected from the group consisting of niacinamide, tocopheryl acetate, sodium ascorbyl phosphate, acetyl glucosamine, trehalose, feverfew extract, glycerin, sodium hyaluronate and capryloyl glycine (and) sarcosine (and) cinnamomum seylanicum bark extract, and mixtures thereof.
  • the composition may comprise a cosmetically acceptable active agent selected from the group consisting of niacinamide, glycerin, sodium hyaluronate, and mixtures thereof.
  • the composition may comprise about 1 to about 5 weight percent of niacinamide, about 0.5 to about 2 weight percent glycerin, and about 0.01 to about 0.1 weight percent of sodium hyaluronate. [0127] The composition may comprise about 2 weight percent of niacinamide, about 1 weight percent glycerin, and about 0.05 weight percent of sodium hyaluronate.
  • the composition may comprise a cosmetically acceptable active agent selected from the group consisting of acetyl glucosamine, niacinamide, and mixtures thereof.
  • the composition may comprise about 2 to about 6 weight percent of acetyl glucosamine and about 1 to about 5 weight percent of niacinamide.
  • the composition may comprise about 4 weight percent of acetyl glucosamine, and about 4 weight percent of niacinamide.
  • compositions were generally prepared as follows.
  • Liposoluble ingredients were mixed together as the “oil phase” in a main tank/pot and heated to 75-85°C to assure proper solubility of all ingredients. After all ingredients were soluble, dispersed materials such as viscosity increasing agents were added. The phase was stirred and homogenized to assure proper dispersion of all materials and then hot water (75-85°C) was poured into the main tank with oil phase under high sheer and homogenization to promote emulsification. After an emulsion was formed, the mixture was cooled to 60°C or below and temperature sensitive ingredients such as MBBT were added while stirring. In the next step, the mixture was cooled to 35-40°C and other temperature sensitive ingredients such as fragrance and antioxidants were added while stirring. Finally, the mixture was homogenized and cooled to 25°C for pH measurement and adjustment with sodium hydroxide if needed.
  • the mixture was cooled to 60°C or below and temperature sensitive ingredients such as MBBT were added while stirring. In the next step, the mixture was cooled to 35-40°C and other temperature sensitive ingredients such as fragrance and antioxidants were added while stirring. Finally, the mixture was homogenized and cooled to 25°C for pH measurement and adjustment with sodium hydroxide if needed.
  • compositions were prepared and tested for SPF using the IN VITRO SPF TEST METHOD.
  • the compositions were formulated in the vehicles shown in Table 1 and contained the UV absorbers and blockers shown in Table 2. For each composition the ratio of SPF to total weight percent of all UV absorbers and UV blockers was calculated. The results are also shown in Table 2.
  • compositions 1 -4 contained the high molecular weight UV absorbers BEMT, EHT, and MBBT. However, Compositions 1 -4 also contained one or more of the low molecular weight UV absorbers avobenzone, octocrylene, octisalate, and homosalate. Compositions 1 -4 had a relatively low ratio of SPF to total weight percent of filters (UV absorbers plus UV blockers), the highest of which was 3.66 (Composition 2). This indicated a low filter pack efficiency. Composition 5 contained no low molecular weight UV absorbers but did not contain DHHB and provided an SPF of 64.77 and a ratio of SPF to total weight percent of filters of only 3.1 .
  • Composition 6 contained the low molecular weight UV absorber PBSA and delivered a ratio of SPF to total weight percent of filters of 3.9.
  • Composition 7 contained no low molecular weight UV absorbers but did not contain DHHB and provided an SPF of only 20.87 and a ratio of SPF to total weight percent of filters of only 0.9.
  • Composition 8 contained no low molecular weight UV absorbers and each of BEMT, EHT, MBBT, DHHB, TiO2, and TBT. It provided the highest SPF of 95.71 and the highest a ratio of SPF to total weight percent of filters of 6.6.
  • compositions were prepared and tested for SPF using the IN VITRO SPF TEST METHOD.
  • the compositions were formulated in the vehicles shown in Table 3 and contained the UV absorbers and blockers shown in Table 4. For each composition the ratio of SPF to total weight percent of all UV absorbers and UV blockers was calculated. The results are also shown in Table 4.
  • compositions 9-16 and 18 each contained the combination of UV absorbers DHHB, BEMT, EHT and MBBT according to the invention and all provided high SPF values of 52.23 to 103.26. In addition, these Compositions all provided high filter pack efficiencies, having ratios of SPF to total weight percent of filters of 4.29 to 6.45. While Composition 17 did not contain MBBT, it did provide an SPF of 52.63 and a ratio of SPF to total weight percent of filters of 4.38. It is believed this is because it contained EHT and BEMT in high concentrations and these UV absorbers have a higher UVB absorbance than MBBT.
  • composition 17 when Composition 17 was tested for SPF in vivo, the result was 44, giving a ratio of SPF to total weight percent of filters of only 3.66.
  • Compositions 15 and 16 provided in vivo SPF results of 72 and 74, with ratios of SPF to total weight percent of filters of 4.61 and 6.06, respectively, which were much higher than those of Composition 17.
  • compositions according to the invention were made using the following UV absorbers and blockers in the following amounts: BEMT 0.5 wt%, EHT
  • compositions also contained 0-20 wt% of the polymeric UV absorber polyglyceryl benzotriazolyl t- butylhydroxyphenylpropionate.
  • the compositions were formulated using the vehicle shown in Table 5.
  • the SPF for each composition was measured using the IN VITRO SPF TEST METHOD. The ratio of SPF to total, combined weight percent of UV absorbers and UV blockers was calculated for each composition.
  • Table 6 shows the results, along with the amount of UV absorbers and UV blockers in each composition.
  • compositions 19-23 containing a combination of UV absorbers and UV blockers according to the invention provided excellent in vitro SPF results of 39.1 to 126.55.
  • the addition of polyglyceryl benzotriazolyl t-butylhydroxyphenylpropionate to Compositions 20-23 synergistically increased SPF versus Composition 19.
  • the best SPF results were obtained using 10 or 15 weight percent of polyglyceryl benzotriazolyl t-butylhydroxyphenylpropionate in combination with BEMT, EHT, MBBT, DHHB and TiO 2 .
  • compositions 27 to 31 according to the invention were prepared using the ingredients shown in Tables 7, 8, 9, and 10.
  • compositions 27 to 31 were found to provide excellent moisturization to skin when topically applied.
  • the UV absorbers and UV blockers in the compositions remained substantially on top of the skin, i.e. , did not permeate the skin, and therefore provided excellent UV protection.
  • the cosmetically acceptable active agents such as niacinamide permeated the skin. In this manner, the efficacy of the UV absorbers and UV blockers, on the one hand, and the efficacy of the cosmetically acceptable active agents, on the other, were both preserved.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Emergency Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)

Abstract

La présente invention concerne une composition d'écran solaire comprenant : (a) diéthylamino hydroxybenzoyl hexyl benzoate; (b) bis-éthylhexyloxyphénol méthoxyphényl triazine; (c) éthylhexyl triazone; et (d) méthylène bis-benzotriazolyl tétraméthylbutylphénol; la composition d'écran solaire étant sensiblement exempte d'absorbeurs UV ayant une masse moléculaire de 380 Daltons ou moins.
PCT/US2024/030473 2023-06-06 2024-05-22 Compositions d'écran solaire à faible pénétration Ceased WO2024253837A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CN202480037628.0A CN121263167A (zh) 2023-06-06 2024-05-22 低穿透的防晒剂组合物
AU2024284595A AU2024284595A1 (en) 2023-06-06 2024-05-22 Low penetration sunscreen compositions
EP24734552.3A EP4724029A1 (fr) 2023-06-06 2024-05-22 Compositions d'écran solaire à faible pénétration
CONC2025/0016231A CO2025016231A2 (es) 2023-06-06 2025-11-25 Composiciones de protector solar de baja penetración

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US202363471362P 2023-06-06 2023-06-06
US63/471,362 2023-06-06
US18/653,546 US20240407991A1 (en) 2023-06-06 2024-05-02 Low penetration sunscreen compositions
US18/653,546 2024-05-02

Publications (2)

Publication Number Publication Date
WO2024253837A1 true WO2024253837A1 (fr) 2024-12-12
WO2024253837A8 WO2024253837A8 (fr) 2025-06-12

Family

ID=91586236

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2024/030473 Ceased WO2024253837A1 (fr) 2023-06-06 2024-05-22 Compositions d'écran solaire à faible pénétration

Country Status (1)

Country Link
WO (1) WO2024253837A1 (fr)

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5869030A (en) 1994-02-23 1999-02-09 Ciba Specialty Chemicals Corporation Sunscreen compositions comprising micronized, insoluble organic UV absorbers
US20120128611A1 (en) * 2009-07-07 2012-05-24 Basf Se Uv filter combinations comprising benzylidene malonates
US20140170251A1 (en) * 2012-12-13 2014-06-19 Precision Dermatology, Inc. Topical Formulations for Increasing the Dermal Concentration of Hyaluronic Acid
US9248092B2 (en) 2012-06-28 2016-02-02 Johnson & Johnson Consumer Inc. Sunscreen compositions containing an ultraviolet radiation-absorbing polymer
US9255180B2 (en) 2012-06-28 2016-02-09 Johnson & Johnson Consumer Inc. Ultraviolet radiation absorbing polyethers
EP3103433A1 (fr) * 2015-06-10 2016-12-14 Acm Composition cosmetique anti-uv et lumiere visible de haute energie
US9795552B2 (en) * 2012-03-19 2017-10-24 The Procter & Gamble Company Superabsorbent polymers and silicone elastomer for use in skin care compositions
US10596087B2 (en) 2016-10-05 2020-03-24 Johnson & Johnson Consumer Inc. Ultraviolet radiation absorbing polymer composition
EP3523350B1 (fr) * 2016-10-05 2022-12-07 Basf Se Composition de polymère absorbant le rayonnement ultraviolet

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5869030A (en) 1994-02-23 1999-02-09 Ciba Specialty Chemicals Corporation Sunscreen compositions comprising micronized, insoluble organic UV absorbers
US20120128611A1 (en) * 2009-07-07 2012-05-24 Basf Se Uv filter combinations comprising benzylidene malonates
US9795552B2 (en) * 2012-03-19 2017-10-24 The Procter & Gamble Company Superabsorbent polymers and silicone elastomer for use in skin care compositions
US9248092B2 (en) 2012-06-28 2016-02-02 Johnson & Johnson Consumer Inc. Sunscreen compositions containing an ultraviolet radiation-absorbing polymer
US9255180B2 (en) 2012-06-28 2016-02-09 Johnson & Johnson Consumer Inc. Ultraviolet radiation absorbing polyethers
US20140170251A1 (en) * 2012-12-13 2014-06-19 Precision Dermatology, Inc. Topical Formulations for Increasing the Dermal Concentration of Hyaluronic Acid
EP3103433A1 (fr) * 2015-06-10 2016-12-14 Acm Composition cosmetique anti-uv et lumiere visible de haute energie
US10596087B2 (en) 2016-10-05 2020-03-24 Johnson & Johnson Consumer Inc. Ultraviolet radiation absorbing polymer composition
EP3523350B1 (fr) * 2016-10-05 2022-12-07 Basf Se Composition de polymère absorbant le rayonnement ultraviolet

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE GNPD [online] MINTEL; 12 May 2023 (2023-05-12), ANONYMOUS: "Cream to Sun Sherbet SPF 50+ PA++++", XP093193461, retrieved from https://www.gnpd.com/sinatra/recordpage/10752814/ Database accession no. 10752814 *
ROKICKI ET AL., GREEN CHEMISTRY, vol. 7, 2005, pages 52

Also Published As

Publication number Publication date
WO2024253837A8 (fr) 2025-06-12

Similar Documents

Publication Publication Date Title
AU2021202557B2 (en) Sunscreen composition
EP3651732B1 (fr) Compositions d'écran solaire à esthétique lumineuse
AU2020230223B2 (en) Sprayable sunscreen composition
US20190192391A1 (en) Sprayable compositions containing metal oxides
EP4684774A1 (fr) Ecran solaire minéral contenant de l'oxyde de zinc et du dioxyde de titane
AU2020230225B2 (en) Transparent sunscreen composition
AU2024284595A1 (en) Low penetration sunscreen compositions
WO2024253837A1 (fr) Compositions d'écran solaire à faible pénétration
US20190015315A1 (en) Light aesthetic sunscreen compositions
WO2026055043A1 (fr) Écran solaire à fps élevé contenant de l'huile de ricin hydrogénée
US20240350380A1 (en) Mineral Sunscreen Compositions

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 24734552

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2025571255

Country of ref document: JP

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: 2025571255

Country of ref document: JP

REG Reference to national code

Ref country code: BR

Ref legal event code: B01A

Ref document number: 112025027044

Country of ref document: BR

WWE Wipo information: entry into national phase

Ref document number: 202517131285

Country of ref document: IN

WWE Wipo information: entry into national phase

Ref document number: AU2024284595

Country of ref document: AU

WWE Wipo information: entry into national phase

Ref document number: 2024734552

Country of ref document: EP

NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 2025137952

Country of ref document: RU

WWP Wipo information: published in national office

Ref document number: 202517131285

Country of ref document: IN

WWE Wipo information: entry into national phase

Ref document number: 2025137952

Country of ref document: RU

ENP Entry into the national phase

Ref document number: 2024734552

Country of ref document: EP

Effective date: 20260107

ENP Entry into the national phase

Ref document number: 2024284595

Country of ref document: AU

Date of ref document: 20240522

Kind code of ref document: A

ENP Entry into the national phase

Ref document number: 2024734552

Country of ref document: EP

Effective date: 20260107

ENP Entry into the national phase

Ref document number: 2024734552

Country of ref document: EP

Effective date: 20260107

ENP Entry into the national phase

Ref document number: 2024734552

Country of ref document: EP

Effective date: 20260107

WWP Wipo information: published in national office

Ref document number: 2025137952

Country of ref document: RU

WWP Wipo information: published in national office

Ref document number: 2024734552

Country of ref document: EP