WO2009036008A1 - Rub-resistant, water-resistant, phase inversion temperature-type sunscreen compositions - Google Patents
Rub-resistant, water-resistant, phase inversion temperature-type sunscreen compositions Download PDFInfo
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- WO2009036008A1 WO2009036008A1 PCT/US2008/075779 US2008075779W WO2009036008A1 WO 2009036008 A1 WO2009036008 A1 WO 2009036008A1 US 2008075779 W US2008075779 W US 2008075779W WO 2009036008 A1 WO2009036008 A1 WO 2009036008A1
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- composition according
- resistance
- rub
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- resistant
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 51
- 230000000475 sunscreen effect Effects 0.000 title claims abstract description 32
- 239000000516 sunscreening agent Substances 0.000 title claims abstract description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 239000000839 emulsion Substances 0.000 claims abstract description 10
- 229920001577 copolymer Polymers 0.000 claims abstract description 9
- 229920006029 tetra-polymer Polymers 0.000 claims abstract description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims abstract description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 8
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims abstract description 8
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000009472 formulation Methods 0.000 claims abstract description 7
- ZKYCLDTVJCJYIB-UHFFFAOYSA-N 2-methylidenedecanamide Chemical compound CCCCCCCCC(=C)C(N)=O ZKYCLDTVJCJYIB-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims abstract description 6
- 239000004615 ingredient Substances 0.000 claims abstract description 6
- 229920000642 polymer Polymers 0.000 claims description 16
- 239000000654 additive Substances 0.000 claims description 15
- 230000000996 additive effect Effects 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 7
- 239000002245 particle Substances 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 description 7
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 7
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 6
- 229940073669 ceteareth 20 Drugs 0.000 description 6
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- 230000036571 hydration Effects 0.000 description 5
- 238000006703 hydration reaction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 4
- 229960001679 octinoxate Drugs 0.000 description 4
- 229960001173 oxybenzone Drugs 0.000 description 4
- 229960004050 aminobenzoic acid Drugs 0.000 description 3
- 229940081733 cetearyl alcohol Drugs 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 3
- OIQXFRANQVWXJF-QBFSEMIESA-N (2z)-2-benzylidene-4,7,7-trimethylbicyclo[2.2.1]heptan-3-one Chemical compound CC1(C)C2CCC1(C)C(=O)\C2=C/C1=CC=CC=C1 OIQXFRANQVWXJF-QBFSEMIESA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- KGKQNDQDVZQTAG-UHFFFAOYSA-N 8-methylnonyl 2,2-dimethylpropanoate Chemical compound CC(C)CCCCCCCOC(=O)C(C)(C)C KGKQNDQDVZQTAG-UHFFFAOYSA-N 0.000 description 2
- -1 Ethylhexyl Chemical group 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229940075529 glyceryl stearate Drugs 0.000 description 2
- 229960003921 octisalate Drugs 0.000 description 2
- 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 1
- AFDXODALSZRGIH-QPJJXVBHSA-N (E)-3-(4-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C=C1 AFDXODALSZRGIH-QPJJXVBHSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- NCIAZCLIFWUDPR-UHFFFAOYSA-N 2-butyl-3,4,5,6-tetramethylphenol Chemical compound CCCCC1=C(C)C(C)=C(C)C(C)=C1O NCIAZCLIFWUDPR-UHFFFAOYSA-N 0.000 description 1
- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 1
- ZPPIGTXUCBQGFQ-UHFFFAOYSA-N 3,4-diethyl-2-hexoxyphenol;2-methoxyphenol Chemical compound COC1=CC=CC=C1O.CCCCCCOC1=C(O)C=CC(CC)=C1CC ZPPIGTXUCBQGFQ-UHFFFAOYSA-N 0.000 description 1
- KKJKXQYVUVWWJP-JLHYYAGUSA-N 4-[(e)-(4,7,7-trimethyl-3-oxo-2-bicyclo[2.2.1]heptanylidene)methyl]benzenesulfonic acid Chemical compound CC1(C)C2CCC1(C)C(=O)\C2=C\C1=CC=C(S(O)(=O)=O)C=C1 KKJKXQYVUVWWJP-JLHYYAGUSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- WYWZRNAHINYAEF-UHFFFAOYSA-N Padimate O Chemical compound CCCCC(CC)COC(=O)C1=CC=C(N(C)C)C=C1 WYWZRNAHINYAEF-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- XNEFYCZVKIDDMS-UHFFFAOYSA-N avobenzone Chemical compound C1=CC(OC)=CC=C1C(=O)CC(=O)C1=CC=C(C(C)(C)C)C=C1 XNEFYCZVKIDDMS-UHFFFAOYSA-N 0.000 description 1
- 229960005193 avobenzone Drugs 0.000 description 1
- 229960001716 benzalkonium Drugs 0.000 description 1
- CYDRXTMLKJDRQH-UHFFFAOYSA-N benzododecinium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 CYDRXTMLKJDRQH-UHFFFAOYSA-N 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- GLCJMPWWQKKJQZ-UHFFFAOYSA-L disodium;2-[4-(4,6-disulfonato-1h-benzimidazol-2-yl)phenyl]-1h-benzimidazole-4,6-disulfonate;hydron Chemical compound [Na+].[Na+].C1=C(S(O)(=O)=O)C=C2NC(C3=CC=C(C=C3)C3=NC4=C(C=C(C=C4N3)S(=O)(=O)O)S([O-])(=O)=O)=NC2=C1S([O-])(=O)=O GLCJMPWWQKKJQZ-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- WNLFPMNBHCWASX-UHFFFAOYSA-N dodecyl 2,2-dimethylpropanoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)(C)C WNLFPMNBHCWASX-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- UVCJGUGAGLDPAA-UHFFFAOYSA-N ensulizole Chemical compound N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 UVCJGUGAGLDPAA-UHFFFAOYSA-N 0.000 description 1
- 229960000655 ensulizole Drugs 0.000 description 1
- 229960004697 enzacamene Drugs 0.000 description 1
- 229940068171 ethyl hexyl salicylate Drugs 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- FMJSMJQBSVNSBF-UHFFFAOYSA-N octocrylene Chemical group C=1C=CC=CC=1C(=C(C#N)C(=O)OCC(CC)CCCC)C1=CC=CC=C1 FMJSMJQBSVNSBF-UHFFFAOYSA-N 0.000 description 1
- 229960000601 octocrylene Drugs 0.000 description 1
- 229940100498 polysilicone-15 Drugs 0.000 description 1
- 229920002282 polysilicones-15 Polymers 0.000 description 1
- KJCLYACXIWMFCC-UHFFFAOYSA-M sodium;5-benzoyl-4-hydroxy-2-methoxybenzenesulfonate Chemical compound [Na+].C1=C(S([O-])(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 KJCLYACXIWMFCC-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 1
- 229960000368 sulisobenzone Drugs 0.000 description 1
- 230000009182 swimming Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
-
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
-
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
-
- 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
- A61K2800/59—Mixtures
- A61K2800/594—Mixtures of polymers
Definitions
- This invention relates to sunscreen compositions, and more particularly to rub-resistant, water-resistant, sprayable phase inversion temperature (PIT) ethoxylated type emulsion sunscreen compositions.
- PIT rub-resistant, water-resistant, sprayable phase inversion temperature
- Certain aspects of the present invention relate to rub-resistant, water-resistant sunscreen compositions for sprayable, PIT ethoxylated type emulsion formulations.
- sunscreen compositions which include
- the polymer additive comprises Allianz OPT , which is present at about 1 % solids, and has a particle size of ⁇ 1 microns.
- the sunscreen compositions in accordance with certain aspects of the invention provide enhanced rub-resistance and superior water-resistance for the user. BRIEF DESCRIPTION OF THE FIGURE
- the present invention is directed to rub-resistant, water-resistant, sprayable phase inversion temperature (PIT) ethoxylated type emulsion sunscreen compositions.
- Sunscreen compositions in accordance with the present invention include (a) an ethoxylated, PIT- type base formulation and (b) a tetrapolymer of methacrylic acid, methyl methacrylate, butyl acrylate and cetyl-eicosinyl methacrylate or a copolymer of acrylates/octylacrylamide.
- Phase inversion temperature (PIT) type emulsion sunscreen compositions typically contain ethoxylated emulsifiers in which a change in the hydration forces between the ethoxylated part and the water part of the emulsion are temperature dependent, which significantly changes the interface.
- Phase inversion temperature (PIT) type emulsions typically have a droplet size of less than about 300 nanometers.
- the sunscreen compositions of the present invention include a polymer additive that increases water resistance and rub resistance of the formulation.
- the polymer additive may be present in an amount of about 0.1 % to about 10%, more particularly from about 0.25% to about 5%, still more particularly from about 0.5% to about 1.5% and in certain cases about 1 % polymer solids based on the total weight of the composition.
- the polymer additive is incorporated into the oil phase while in other embodiments the polymer additive is incorporated into the composition as a post additive.
- the polymer additive may be a tetrapolymer emulsion polymerization product of methacrylic acid, methyl methacrylate, butyl acrylate and cetyl-eicosinyl methacrylate.
- a particularly useful tetrapolymer of this type is ALLIANZTM OPT (INCI name acrylates/C-12-22 alkylmethacrylate copolymer) commercially available from ISP as an aqueous dispersion at 47% to 49% solids.
- the polymer additive may be a high molecular weight carboxylated acrylic copolymer, more particularly a copolymer of acrylates/octylacrylamide.
- a particularly useful copolymer of this type is DERMACRYL® 79 commercially available from National Starch.
- the sunscreen compositions of the invention can contain one or more active UVA and UVB sunscreen compounds, e.g., avobenzone, benzophenone-3, p-Aminobenzoic acid (PABA), Camphor benzalkonium methosulfate, Phenylbenzimidazole sulfonic acid, Terephthalidene dicamphor sulfonic acid, Benzylidene camphor sulfonic acid, Octocrylene, Polyacrylamidomethyl benzylidene camphor, Ethylhexyl methoxycinnamate, PEG- 25 PABA, lsoamyl p-methoxycinnamate, Ethylhexyl thazone, Dromethzole thsiloxane, Diethylhexyl butamido thazone, 4-Methylbenzylidene camphor, 3- Benzylidene camphor, Ethylhexyl
- Water resistance as set forth herein is measured in accordance with the following procedure. In-vitro skin (IMS Testing Group) is hydrated for 12 to 18 hours in a hydration chamber (82% water/ 18% glycerin solution). Four (4) samples and one reference/blank are prepared by applying 6 to 8 mg. of the sunscreen sample onto each sample and allowing the sample to re-hydrate for 20 minutes.
- Retention water resistance
- compositions according to certain aspects of the present invention provide water resistance (as determined by the procedures set forth herein) of at least 90%, more particularly at least 95%, and in certain cases about 100%.
- the described in vitro test method has been confirmed through corresponding in vivo tests.
- Rub resistance as set forth herein is measured in accordance with the following procedure which simulates swimming and towel drying.
- In-vitro skin IMS Testing Group
- a hydration chamber 82% water/ 18% glycerin solution.
- Four (4) samples and one reference/blank are prepared by applying 6 to 8 mg. of the sunscreen sample onto each sample and allowing the sample to re-hydrate for 20 minutes.
- a cotton towel (4"x 5" piece) is wrapped around the friction boat (abrasion boat with auxiliary 1 Ib. weight measuring 2"X4") and secured with double-sided tape.
- the boat is placed into the inner side of the arm of the Wear Tester.
- the Wear tester is set at Speed 3 and the towel is allowed to make 3.5 passes (one pass is to the left and then back to the right to the starting position).
- the samples and tape are removed and the samples are placed in the hydration chamber for 120 minutes.
- Final readings are taken (each sample vs. the reference) for each sample scanned at four orientations rotating 90 degrees after each reading. The readings are taken at the highest peak between 250-400 nm.
- Retention (rub resistance) is calculated by dividing the final readings by the initial readings and multiplying by 100. The average and standard deviation are calculated and recorded. Inconsistently high or low values should be omitted from the calculation of the retention.
- compositions according to certain aspects of the present invention provide rub resistance (as determined by the process described herein) of at least 60%, more particularly at least 70%, still more particularly at least 80%, in some cases at least 90%, and in certain cases about 100%.
- Eumulgin B2 (Ceteareth 20) 2.70 Emulgade SE (Glyceryl Stearate, Ceteareth-12,
- Escalol 557 (Octinoxate) 6.00 Escalol 567 (Benzophenone-3) 2.00
- Eumulgin B2 (Ceteareth-20) 2.70
- Emulgade SE (Glyceryl stearate, Ceteareth-12, 4.30
- Emulgade SE (Glyaryl stearate, Ceteareth-12, 4.30
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)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
Abstract
The present invention relates to a rub-resistant, water-resistant, phase inversion temperature-type sunscreen composition comprising (a) an ethoxylated emulsion PIT- type base formulation and an active sunscreen ingredient therein, and (b) a tetrapolymer of methacrylic acid, methyl methacrylate, butyl acrylate and cetyl-eicosinyl methacrylate or a copolymer of acrylates/octylacrylamide.
Description
RUB-RESISTANT, WATER-RESISTANT, PHASE INVERSION TEMPERATURE -TYPE SUNSCREEN COMPOSITIONS
CROSS REFERENCE TO RELATED APPLICATION
This Application claims the benefit of U.S. Provisional Application Serial Number 60/971 ,076 filed September 10, 2007, the contents of which are hereby incorporated by reference.
FIELD OF THE INVENTION
[0001] This invention relates to sunscreen compositions, and more particularly to rub-resistant, water-resistant, sprayable phase inversion temperature (PIT) ethoxylated type emulsion sunscreen compositions.
BACKGROUND OF THE INVENTION
[0002] Current spray applications for suncare emulsion systems historically have not provided both excellent rub-resistance and superior water-resistance.
[0003] Certain aspects of the present invention relate to rub-resistant, water-resistant sunscreen compositions for sprayable, PIT ethoxylated type emulsion formulations.
SUMMARY OF THE INVENTION
[0004] What is described herein are sunscreen compositions which include
(a) an ethoxylated, PIT- type base formulation and (b) a polymer additive selected from the group consisting of (i) a tetrapolymer of methacrylic acid, methyl methacrylate, butyl acrylate and cetyl-eicosinyl methacrylate, (ii) a copolymer of acrylates/octylacrylamide and mixtures thereof. In accordance with certain embodiments, the polymer additive comprises Allianz OPT , which is present at about 1 % solids, and has a particle size of <1 microns.
[0005] The sunscreen compositions in accordance with certain aspects of the invention provide enhanced rub-resistance and superior water-resistance for the user.
BRIEF DESCRIPTION OF THE FIGURE
[0006] The Figure shows PIT sunscreen compositions (a) without polymer
(b) with added Dermacryl® 79 polymer, and (c) with added Allianz OPT polymer, and their rub-resistance and water-resistant properties, respectively.
DETAILED DESCRIPTION OF THE INVENTION
[0007] The present invention is directed to rub-resistant, water-resistant, sprayable phase inversion temperature (PIT) ethoxylated type emulsion sunscreen compositions. Sunscreen compositions in accordance with the present invention include (a) an ethoxylated, PIT- type base formulation and (b) a tetrapolymer of methacrylic acid, methyl methacrylate, butyl acrylate and cetyl-eicosinyl methacrylate or a copolymer of acrylates/octylacrylamide.
[0008] Phase inversion temperature (PIT) type emulsion sunscreen compositions typically contain ethoxylated emulsifiers in which a change in the hydration forces between the ethoxylated part and the water part of the emulsion are temperature dependent, which significantly changes the interface. Phase inversion temperature (PIT) type emulsions typically have a droplet size of less than about 300 nanometers.
[0009] The sunscreen compositions of the present invention include a polymer additive that increases water resistance and rub resistance of the formulation. The polymer additive may be present in an amount of about 0.1 % to about 10%, more particularly from about 0.25% to about 5%, still more particularly from about 0.5% to about 1.5% and in certain cases about 1 % polymer solids based on the total weight of the composition. In accordance with certain embodiments of the invention, the polymer additive is incorporated into the oil phase while in other embodiments the polymer additive is incorporated into the composition as a post additive.
[0010] In accordance with a particularly useful aspect of the invention, the polymer additive may be a tetrapolymer emulsion polymerization product of methacrylic acid, methyl methacrylate, butyl acrylate and cetyl-eicosinyl methacrylate. A particularly useful tetrapolymer of this type is ALLIANZ™ OPT
(INCI name acrylates/C-12-22 alkylmethacrylate copolymer) commercially available from ISP as an aqueous dispersion at 47% to 49% solids.
[0011] In accordance with another embodiment of the present invention, the polymer additive may be a high molecular weight carboxylated acrylic copolymer, more particularly a copolymer of acrylates/octylacrylamide. A particularly useful copolymer of this type is DERMACRYL® 79 commercially available from National Starch.
[0012] The sunscreen compositions of the invention can contain one or more active UVA and UVB sunscreen compounds, e.g., avobenzone, benzophenone-3, p-Aminobenzoic acid (PABA), Camphor benzalkonium methosulfate, Phenylbenzimidazole sulfonic acid, Terephthalidene dicamphor sulfonic acid, Benzylidene camphor sulfonic acid, Octocrylene, Polyacrylamidomethyl benzylidene camphor, Ethylhexyl methoxycinnamate, PEG- 25 PABA, lsoamyl p-methoxycinnamate, Ethylhexyl thazone, Dromethzole thsiloxane, Diethylhexyl butamido thazone, 4-Methylbenzylidene camphor, 3- Benzylidene camphor, Ethylhexyl salicylate, Ethylhexyl dimethyl PABA, Benzophenone-4, Benzophenone-5, Methylene bis-benzthazolyl tetramethylbutylphenol, Disodium phenyl dibenzimidazole tetrasulfonate, Bis- ethylhexyloxyphenol methoxyphenol thazine, and Polysilicone-15. Other compounds described in the art for the purpose may also be used.
[0013] Water resistance as set forth herein is measured in accordance with the following procedure. In-vitro skin (IMS Testing Group) is hydrated for 12 to 18 hours in a hydration chamber (82% water/ 18% glycerin solution). Four (4) samples and one reference/blank are prepared by applying 6 to 8 mg. of the sunscreen sample onto each sample and allowing the sample to re-hydrate for 20 minutes.
[0014] Initial UV absorbance readings are measured (each sample vs. the reference) for each sample scanned at four orientations rotating 90 degrees after each reading. Readings are taken at the highest peak between 250-400 nm on a dual beam UV-Vis spectrophotometer with slide holder. The four (4) samples are placed in the water bath (25°C with propeller mixing at 50 rpm) for 80 minutes. The samples are removed from the water bath and allowed to dry for 10 minutes.
The samples are placed in the hydration chamber for 120 minutes. Readings are taken (each sample vs. the reference) for each sample scanned at four orientations rotating 90 degrees after each reading. Readings are taken at the highest peak between 250-400 nm.
[0015] Retention (water resistance) is calculated by dividing the final readings by the initial readings and multiplying by 100. The average and standard deviation are calculated and recorded. Inconsistently high or low values should be omitted from the calculation of the retention.
[0016] Compositions according to certain aspects of the present invention provide water resistance (as determined by the procedures set forth herein) of at least 90%, more particularly at least 95%, and in certain cases about 100%. The described in vitro test method has been confirmed through corresponding in vivo tests.
[0017] Rub resistance as set forth herein is measured in accordance with the following procedure which simulates swimming and towel drying. In-vitro skin (IMS Testing Group) is hydrated for 12 to 18 hours in a hydration chamber (82% water/ 18% glycerin solution). Four (4) samples and one reference/blank are prepared by applying 6 to 8 mg. of the sunscreen sample onto each sample and allowing the sample to re-hydrate for 20 minutes.
[0018] Initial UV absorbance readings are taken (each sample vs. the reference) for each sample scanned at four orientations rotating 90 degrees after each reading. Readings are taken at the highest peak between 250-400 nm using a UV-Vis spectrophotometer with slide holder (two beam).
[0019] The completed samples are placed in the water bath (25°C with propeller mixing) for 80 minutes. The samples are removed from water bath. Double-sided tape is placed on the underside of the sample slides and placed on a Friction machine (Gardco: Washability and Wear Tester - Linear Motion Test Equipment Model D10VF/ Cat# WA-2155), sample side up.
[0020] After the samples are secured, a cotton towel (4"x 5" piece) is wrapped around the friction boat (abrasion boat with auxiliary 1 Ib. weight measuring 2"X4") and secured with double-sided tape. The boat is placed into the
inner side of the arm of the Wear Tester. The Wear tester is set at Speed 3 and the towel is allowed to make 3.5 passes (one pass is to the left and then back to the right to the starting position). After the wear test is completed, the samples and tape are removed and the samples are placed in the hydration chamber for 120 minutes.
[0021] Final readings are taken (each sample vs. the reference) for each sample scanned at four orientations rotating 90 degrees after each reading. The readings are taken at the highest peak between 250-400 nm. Retention (rub resistance) is calculated by dividing the final readings by the initial readings and multiplying by 100. The average and standard deviation are calculated and recorded. Inconsistently high or low values should be omitted from the calculation of the retention.
[0022] Compositions according to certain aspects of the present invention provide rub resistance (as determined by the process described herein) of at least 60%, more particularly at least 70%, still more particularly at least 80%, in some cases at least 90%, and in certain cases about 100%.
[0023] The invention will now be described by reference to the following non-limiting examples of invention compositions.
EXAMPLE 1 - Negative Control
P.I.T. SUNSCREEN FORMULATION WITH NO ADDED POLYMER
INGREDIENT % W/W Water Phase
Dl Water 73.3
Glycerin 2.00
Oil Phase
Eumulgin B2 (Ceteareth 20) 2.70 Emulgade SE (Glyceryl Stearate, Ceteareth-12,
Ceteareth-20, cetearyl Alcohol) 4.30
Ceraphyl SLK (Dodecyl Neopentanoate) 4.00
Escalol 557 (Octinoxate) 6.00
Escalol 567 (Benzophenone-3) 2.00
Post-Additive
Liquid Germall® Plus post-additive 0.6
PROCESS:
1. Heat water phase to 800C
2. Heat oil phase to 75°C
3. Heat up to 78° C to invert
4. Post-add Germall® at 45° or below PROPERTIES (Figure):
Rub-Resistance - Poor
Water-Resistance - Poor EXAMPLE 2 - Inventive Example
PIT SUNSCREEN WITH DERMACRYL®79 Added Polymer INGREDIENT % W/W
Water Phase
Dl Water 74.4
Glycerin 2.00
Oil Phase
Eumulgin B2 (Ceteareth-20) 2.70
Emulgade SE (Glyceryl stearate, Ceteareth-12, 4.30
Ceteareth-20, Cetearyl alcohol)
Ceraphyl SLK (Isodecyl Neopentanoate) 4.00
Escalol 557 (Octinoxate) 6.00
Escalol 567 (Benzophenone-3) 2.00
Escalol 587 (Octisalate) 3.00
Dermacryl® 79 1 .00
Post-Additive
Liquid Germall® Plus 0.60
PROPERTIES (Figure):
Rub-Resistance - Good
Water-Resistance - Excellent EXAMPLE 3 - Inventive Example PIT SUNSCREEN COMPOSITION
INGREDIENT % W/W Water Phase
Dl Water 73.3
Glycerin 2.00
Oil Phase
Eumulgin B2 (Ceteareth 20) 2.70
Emulgade SE (Glyaryl stearate, Ceteareth-12, 4.30
Ceteareth-20, Cetearyl Alcohol)
Ceraphyl SLK (Isodecyl Neopentanoate) 4.00
Escalol 557 (Octinoxate) 6.00
Escalol 567 (Benzophenone-3) 2.00
Escalol 587(Octisalate) 3.00
Post -Additive
Liquid Germall® Plus 0.60
Allianz OPT 2.10
PROPERTIES (Figure):
Rub-Resistance - Enhanced Water-Resistance - Excellent
[0024] The invention has been described in detail with particular reference to preferred embodiments thereof, but it will be understood that variations and modifications can be effected within the spirit and scope of the invention.
Claims
1. An enhanced rub-resistant, water-resistant PIT sunscreen composition comprising: a) an ethoxylated PIT emulsion base formulation with an active sunscreen ingredient; and b) a polymer additive selected from the group consisting of (i) a tetrapolymer of methacrylic acid, methyl methacrylate, butyl acrylate and cetyl- eicosinyl methacrylate, (ii) a copolymer of acrylate/octylacrylamide and mixtures thereof.
2. A composition according to claim 1 wherein (b) is present at about 0.25% to about 5% solids.
3. A composition according to claim 1 wherein (b) is present at about 0.5% to about 1 .5% solids.
4. A composition according to claim 1 wherein (b) comprises a tetrapolymer of methacrylic acid, methyl methacrylate, butyl acrylate and cetyl- eicosinyl methacrylate.
5. A composition according to claim 4 wherein (b) comprises acrylates/Ci2-22 alkylmethacrylate copolymer with a particle size of less than 1 microns.
6. A composition according to claim 4 wherein (b) is present at about 0.5% to about 1 .5% solids.
7. A composition according to claim 6 which has a rub-resistance of at least 70%.
8. A composition according to claim 6 which has a rub-resistance of at least 80%.
9. A composition according to claim 1 which has a rub-resistance of at least 60%.
10. A composition according to claim 1 which has a rub-resistance of at least 84%.
11 . A composition according to claim 1 which has a water-resistance of at least 90%.
12. A composition according to claim 8 which has a water-resistance of at least 90%.
13. A sprayable sunscreen composition comprising: a) an active sunscreen ingredient; and b) a polymer additive selected from the group consisting of (i) a tetrapolymer of methacrylic acid, methyl methacrylate, butyl acrylate and cetyl- eicosinyl methacrylate, (ii) a copolymer of acrylate/octylacrylamide and mixtures thereof, wherein the composition is a phase inversion temperature emulsion with a droplet size of less than 300nm.
14. A sunscreen composition in accordance with claim 13 wherein (b) is present at about 0.5% to about 1.5% solids.
15. A sunscreen composition according to claim 14 wherein (b) comprises a tetrapolymer of methacrylic acid, methyl methacrylate, butyl acrylate and cetyl-eicosinyl methacrylate.
16. A sunscreen composition according to claim 15 wherein (b) has a particle size of less than 1 microns.
17. A sunscreen composition according to claim 16 which has a rub- resistance of at least 80%.
18. A sunscreen composition according to claim 17 which has a water- resistance of at least 90%.
19. A sunscreen composition according to claim 14 which has a rub- resistance of at least 80%.
20. A sunscreen composition according to claim 19 which has a water- resistance of at least 90%.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US97107607P | 2007-09-10 | 2007-09-10 | |
| US60/971,076 | 2007-09-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2009036008A1 true WO2009036008A1 (en) | 2009-03-19 |
Family
ID=40452432
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2008/075779 WO2009036008A1 (en) | 2007-09-10 | 2008-09-10 | Rub-resistant, water-resistant, phase inversion temperature-type sunscreen compositions |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2009036008A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012084601A3 (en) * | 2010-12-22 | 2012-09-20 | Beiersdorf Ag | Cosmetic or dermatological preparations having a high proportion of skin moistening agent |
| WO2012084603A3 (en) * | 2010-12-22 | 2012-09-27 | Beiersdorf Ag | Cosmetic or dermatological uv protection preparations comprising a combination of polyacylate and polyacrylamide thickener |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5288493A (en) * | 1991-05-17 | 1994-02-22 | National Starch And Chemical Investment Holding Corporation | Skin care compositions with improved rub-off resistance |
| US20020076390A1 (en) * | 2000-10-25 | 2002-06-20 | 3M Innovative Properties Company | Acrylic-based copolymer compositions for cosmetic and personal care |
| US20050058680A1 (en) * | 2002-02-26 | 2005-03-17 | Beiersdorf Ag | Process for the preparation of an emulsion |
| US20060110352A1 (en) * | 2004-10-15 | 2006-05-25 | Clariant Gmbh | Cosmetic, pharmaceutical and dermatological compositions |
-
2008
- 2008-09-10 WO PCT/US2008/075779 patent/WO2009036008A1/en active Application Filing
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5288493A (en) * | 1991-05-17 | 1994-02-22 | National Starch And Chemical Investment Holding Corporation | Skin care compositions with improved rub-off resistance |
| US20020076390A1 (en) * | 2000-10-25 | 2002-06-20 | 3M Innovative Properties Company | Acrylic-based copolymer compositions for cosmetic and personal care |
| US20050058680A1 (en) * | 2002-02-26 | 2005-03-17 | Beiersdorf Ag | Process for the preparation of an emulsion |
| US20060110352A1 (en) * | 2004-10-15 | 2006-05-25 | Clariant Gmbh | Cosmetic, pharmaceutical and dermatological compositions |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012084601A3 (en) * | 2010-12-22 | 2012-09-20 | Beiersdorf Ag | Cosmetic or dermatological preparations having a high proportion of skin moistening agent |
| WO2012084603A3 (en) * | 2010-12-22 | 2012-09-27 | Beiersdorf Ag | Cosmetic or dermatological uv protection preparations comprising a combination of polyacylate and polyacrylamide thickener |
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