NZ602661B - Topical sunscreen compositions - Google Patents
Topical sunscreen compositions Download PDFInfo
- Publication number
- NZ602661B NZ602661B NZ602661A NZ60266112A NZ602661B NZ 602661 B NZ602661 B NZ 602661B NZ 602661 A NZ602661 A NZ 602661A NZ 60266112 A NZ60266112 A NZ 60266112A NZ 602661 B NZ602661 B NZ 602661B
- Authority
- NZ
- New Zealand
- Prior art keywords
- composition
- oil
- oil portion
- water
- organic
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 113
- 230000000475 sunscreen Effects 0.000 title description 12
- 239000000516 sunscreening agent Substances 0.000 title description 12
- 230000000699 topical Effects 0.000 title description 4
- 239000003921 oil Substances 0.000 claims abstract description 135
- 239000004904 UV filter Substances 0.000 claims abstract description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 51
- 239000007787 solid Substances 0.000 claims abstract description 28
- DXGLGDHPHMLXJC-UHFFFAOYSA-N Oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229960001173 oxybenzone Drugs 0.000 claims abstract description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 52
- -1 alkyl benzoate Chemical compound 0.000 claims description 27
- 229960005193 avobenzone Drugs 0.000 claims description 15
- XNEFYCZVKIDDMS-UHFFFAOYSA-N Avobenzone Chemical group C1=CC(OC)=CC=C1C(=O)CC(=O)C1=CC=C(C(C)(C)C)C=C1 XNEFYCZVKIDDMS-UHFFFAOYSA-N 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 14
- 229920000642 polymer Polymers 0.000 claims description 13
- ZDQWESQEGGJUCH-UHFFFAOYSA-N Diisopropyl adipate Chemical compound CC(C)OC(=O)CCCCC(=O)OC(C)C ZDQWESQEGGJUCH-UHFFFAOYSA-N 0.000 claims description 11
- 229940031578 diisopropyl adipate Drugs 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- VILAVOFMIJHSJA-UHFFFAOYSA-N Dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 33
- BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract description 2
- 210000003491 Skin Anatomy 0.000 description 18
- 239000003380 propellant Substances 0.000 description 15
- 239000001993 wax Substances 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 230000002087 whitening Effects 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- BARWIPMJPCRCTP-CLFAGFIQSA-N oleyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC BARWIPMJPCRCTP-CLFAGFIQSA-N 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 150000003626 triacylglycerols Chemical class 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 239000011550 stock solution Substances 0.000 description 4
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 4
- 235000008170 thiamine pyrophosphate Nutrition 0.000 description 4
- 238000002211 ultraviolet spectrum Methods 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- UQEAIHBTYFGYIE-UHFFFAOYSA-N Hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 3
- WSSJONWNBBTCMG-UHFFFAOYSA-N Homosalate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C1=CC=CC=C1O WSSJONWNBBTCMG-UHFFFAOYSA-N 0.000 description 3
- XUGNVMKQXJXZCD-UHFFFAOYSA-N Isopropyl palmitate Chemical group CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000005215 alkyl ethers Chemical class 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- ZZKLBPLJHJQUJL-UHFFFAOYSA-N benzoic acid;propanoic acid Chemical compound CCC(O)=O.OC(=O)C1=CC=CC=C1 ZZKLBPLJHJQUJL-UHFFFAOYSA-N 0.000 description 3
- BXLREEYNIFUGAF-UHFFFAOYSA-N carbonic acid;hexadecanoic acid Chemical compound OC(O)=O.CCCCCCCCCCCCCCCC(O)=O BXLREEYNIFUGAF-UHFFFAOYSA-N 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 229940008099 dimethicone Drugs 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- 239000003974 emollient agent Substances 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000002209 hydrophobic Effects 0.000 description 3
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 230000001681 protective Effects 0.000 description 3
- LCULPNBYCKULDR-VGWJSVSZSA-N (6Z)-3-(2-ethylhexoxy)-6-[(4Z)-4-[4-(2-ethylhexoxy)-6-oxocyclohexa-2,4-dien-1-ylidene]-6-(4-methoxyphenyl)-1H-1,3,5-triazin-2-ylidene]cyclohexa-2,4-dien-1-one Chemical compound C1=CC(OCC(CC)CCCC)=CC(=O)\C1=C(/NC(=N\1)C=2C=CC(OC)=CC=2)NC/1=C\1C(=O)C=C(OCC(CC)CCCC)C=C/1 LCULPNBYCKULDR-VGWJSVSZSA-N 0.000 description 2
- JGUMTYWKIBJSTN-UHFFFAOYSA-N 2-ethylhexyl 4-[[4,6-bis[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 JGUMTYWKIBJSTN-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-Aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- 229960004101 Bemotrizinol Drugs 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- HUVYTMDMDZRHBN-UHFFFAOYSA-N Drometrizole trisiloxane Chemical compound C[Si](C)(C)O[Si](C)(O[Si](C)(C)C)CC(C)CC1=CC(C)=CC(N2N=C3C=CC=CC3=N2)=C1O HUVYTMDMDZRHBN-UHFFFAOYSA-N 0.000 description 2
- 229960004881 Homosalate Drugs 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinylpyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- 240000002853 Nelumbo nucifera Species 0.000 description 2
- 235000006508 Nelumbo nucifera Nutrition 0.000 description 2
- 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 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000010192 crystallographic characterization Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000005594 diketone group Chemical group 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 210000003702 immature single positive T cell Anatomy 0.000 description 2
- 229940075495 isopropyl palmitate Drugs 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229960000601 octocrylene Drugs 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000306 polymethylpentene Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- MBHCWRKFAXKMRT-UHFFFAOYSA-N propanoic acid;1-tetradecoxytetradecane Chemical compound CCC(O)=O.CCCCCCCCCCCCCCOCCCCCCCCCCCCCC MBHCWRKFAXKMRT-UHFFFAOYSA-N 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 235000003702 sterols Nutrition 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 239000007762 w/o emulsion Substances 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-(1R,3R,4S)-menthol Chemical group CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 1
- HEOCBCNFKCOKBX-CRAIPNDOSA-N (1S,4S)-4,7,7-trimethyl-2-[(4-methylphenyl)methylidene]bicyclo[2.2.1]heptan-3-one Chemical compound C1=CC(C)=CC=C1C=C1C(=O)[C@@]2(C)CC[C@H]1C2(C)C HEOCBCNFKCOKBX-CRAIPNDOSA-N 0.000 description 1
- LXODQLXKQIJVNK-UHFFFAOYSA-N 2-(2-benzoyloxypropoxy)propyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC(C)COC(C)COC(=O)C1=CC=CC=C1 LXODQLXKQIJVNK-UHFFFAOYSA-N 0.000 description 1
- KXTAOXNYQGASTA-UHFFFAOYSA-L 2-benzylidenepropanedioate Chemical compound [O-]C(=O)C(C([O-])=O)=CC1=CC=CC=C1 KXTAOXNYQGASTA-UHFFFAOYSA-L 0.000 description 1
- TYYHDKOVFSVWON-UHFFFAOYSA-N 2-butyl-2-methoxy-1,3-diphenylpropane-1,3-dione Chemical compound C=1C=CC=CC=1C(=O)C(OC)(CCCC)C(=O)C1=CC=CC=C1 TYYHDKOVFSVWON-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N 2-stearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- UBNYRXMKIIGMKK-UHFFFAOYSA-N 3-methylbutyl 3-(4-methoxyphenyl)prop-2-enoate Chemical compound COC1=CC=C(C=CC(=O)OCCC(C)C)C=C1 UBNYRXMKIIGMKK-UHFFFAOYSA-N 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-O 4,5-dihydro-1H-imidazol-1-ium Chemical compound C1CN=C[NH2+]1 MTNDZQHUAFNZQY-UHFFFAOYSA-O 0.000 description 1
- 229940000641 4-Aminobenzoic Acid Drugs 0.000 description 1
- 229940064734 Aminobenzoate Drugs 0.000 description 1
- 229960003055 BISOCTRIZOLE Drugs 0.000 description 1
- FQUNFJULCYSSOP-UHFFFAOYSA-N Bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 1
- FPWFTWZABNIDGA-UHFFFAOYSA-N C(C)C1(CCC(CC1)CCCCCC)CC Chemical compound C(C)C1(CCC(CC1)CCCCCC)CC FPWFTWZABNIDGA-UHFFFAOYSA-N 0.000 description 1
- NAEPHZSMYIQDBV-UHFFFAOYSA-N CC1=C(O)C=C2NN=NC2=C1C1=CC=CC=C1 Chemical compound CC1=C(O)C=C2NN=NC2=C1C1=CC=CC=C1 NAEPHZSMYIQDBV-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-L CHEBI:8154 Chemical class [O-]P([O-])=O ABLZXFCXXLZCGV-UHFFFAOYSA-L 0.000 description 1
- DSSYKIVIOFKYAU-UHFFFAOYSA-N Camphor Chemical compound C1CC2(C)C(=O)CC1C2(C)C DSSYKIVIOFKYAU-UHFFFAOYSA-N 0.000 description 1
- 229960000846 Camphor Drugs 0.000 description 1
- 229940073532 Candelilla Wax Drugs 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- AKNXMRHLLPIDLY-UHFFFAOYSA-N Diethylamino hydroxybenzoyl hexyl benzoate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)C1=CC=CC(N(CC)CC)=C1O AKNXMRHLLPIDLY-UHFFFAOYSA-N 0.000 description 1
- MEZZCSHVIGVWFI-UHFFFAOYSA-N Dioxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1O MEZZCSHVIGVWFI-UHFFFAOYSA-N 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- IUJAMGNYPWYUPM-UHFFFAOYSA-N Hentriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC IUJAMGNYPWYUPM-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 229940039717 Lanolin Drugs 0.000 description 1
- SOXAGEOHPCXXIO-DVOMOZLQSA-N Menthyl anthranilate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)C1=CC=CC=C1N SOXAGEOHPCXXIO-DVOMOZLQSA-N 0.000 description 1
- 235000006510 Nelumbo pentapetala Nutrition 0.000 description 1
- 229960003921 Octisalate Drugs 0.000 description 1
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Octyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 1
- 229940100498 POLYSILICONE-15 Drugs 0.000 description 1
- 229940096958 PPG-15 STEARYL ETHER BENZOATE Drugs 0.000 description 1
- 241000283222 Physeter catodon Species 0.000 description 1
- 239000004698 Polyethylene (PE) Substances 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O Pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L Sulphite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 210000004243 Sweat Anatomy 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K [O-]P([O-])([O-])=O Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000000172 allergic Effects 0.000 description 1
- 125000000909 amidinium group Chemical group 0.000 description 1
- XXXHSQBVHSJQKS-UHFFFAOYSA-N amino benzoate Chemical compound NOC(=O)C1=CC=CC=C1 XXXHSQBVHSJQKS-UHFFFAOYSA-N 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000000111 anti-oxidant Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 description 1
- 229930007890 camphor Natural products 0.000 description 1
- 239000004204 candelilla wax Substances 0.000 description 1
- 235000013868 candelilla wax Nutrition 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000007765 cera alba Substances 0.000 description 1
- 229940074979 cetyl palmitate Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229960001630 diethylamino hydroxybenzoyl hexyl benzoate Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 229960004960 dioxybenzone Drugs 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- SRVSYCCHRDXMMS-UHFFFAOYSA-N dodecan-5-yl 2-hydroxybenzoate Chemical compound CCCCCCCC(CCCC)OC(=O)C1=CC=CC=C1O SRVSYCCHRDXMMS-UHFFFAOYSA-N 0.000 description 1
- GULIJHQUYGTWSO-UHFFFAOYSA-N dodecyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCC GULIJHQUYGTWSO-UHFFFAOYSA-N 0.000 description 1
- 230000037336 dry skin Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002708 enhancing Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 150000004676 glycans Polymers 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 230000005661 hydrophobic surface Effects 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 229910000460 iron oxide Inorganic materials 0.000 description 1
- 235000013980 iron oxide Nutrition 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 229940119170 jojoba wax Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229960002248 meradimate Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N methoxyethyl Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000012184 mineral wax Substances 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- PXDJXZJSCPSGGI-UHFFFAOYSA-N palmityl palmitate Chemical compound CCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC PXDJXZJSCPSGGI-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920000765 poly(2-oxazolines) Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000004804 polysaccharides Polymers 0.000 description 1
- 229920002282 polysilicones-15 Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002335 preservative Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- ZTHYODDOHIVTJV-UHFFFAOYSA-N propyl 3,4,5-trihydroxybenzoate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-M stearate Chemical compound CCCCCCCCCCCCCCCCCC([O-])=O QIQXTHQIDYTFRH-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 210000001519 tissues Anatomy 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- 239000012178 vegetable wax Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- 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
- A61K2800/31—Anhydrous
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
-
- 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
- A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
-
- 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
Abstract
602661 Disclosed is a composition comprising: at least 10% by weight of a C2 or C3 mono-alcohol (ethanol or propanol); a solid organic UV-filter (oxybenzone) dissolved therein; an oil portion comprising one or more oils, wherein the oil portion is miscible with the C2 or C3 mono-alcohol, wherein the oil portion has an interfacial tension with water of greater than 9mN/m and less than 32.5mN/m, and wherein the composition has a volume fraction of the oil portion relative to the oil portion plus the C2 or C3 mono-alcohol that is about 0.33 or greater, wherein said UV-filter is selected such that the composition comprises about 1.5% by weight or less of a solid, organic UV-filter dissolved therein, and wherein the composition comprises less than 1 percent by weight water. he oil portion has an interfacial tension with water of greater than 9mN/m and less than 32.5mN/m, and wherein the composition has a volume fraction of the oil portion relative to the oil portion plus the C2 or C3 mono-alcohol that is about 0.33 or greater, wherein said UV-filter is selected such that the composition comprises about 1.5% by weight or less of a solid, organic UV-filter dissolved therein, and wherein the composition comprises less than 1 percent by weight water.
Description
NEW ZEALAND
PATENTS ACT, 1953
COMPLETE SPECIFICATION
TOPICAL SUNSCREEN COMPOSITIONS
We, JOHNSON & JOHNSON CONSUMER COMPANIES, INC., a corporation of the State
of New Jersey, United States of America, of 199 Grandview Road, Skillman, New Jersey
08558, United States of America, do hereby declare the invention for which we pray that a
patent may be granted to us, and the method by which it is to be performed, to be particularly
described in and by the following statement:
TOPICAL SUNSCREEN COMPOSITIONS
FIELD OF THE INVENTION
The present invention relates to topical sunscreen compositions having the ability to
be successfully applied to wet skin.
BACKGROUND OF THE INVENTION
Conventional sunscreen products generally take the form of ultraviolet (UV)-filter
compounds and/or particulate UV-screening compounds (collectively, “sunscreen actives”)
that are solublized, emulsified, or dispersed in a vehicle, which is topically applied to the
skin. The sunscreen actives, typically through the aid of polymers and other ingredients
included in the vehicle, form a thin, protective, and often water-resistant layer on the skin.
The applicants have recognized that, while certain products are successful at
providing a durable protective barrier when applied to dry skin, such is not typically the result
when applied to skin that is damp with sweat or has residual water thereon. In fact, when
applied to wet skin, the tendency of conventional sunscreen products is to dilute the
sunscreen actives, smear, and form an incomplete film, often one that flakes or peels off the
skin, and/or takes on a pasty, white appearance. The end result is unattractive, and renders
the skin with poor protection from the sun’s rays.
Others have contemplated a solution to this problem by using a water-in-oil emulsifier
to “self-emulsify,” presumably in the presence of residual water present on the skin.
However, the applicants have recognized that severe aesthetic and performance problems still
exist in most all “wet skin” sunscreen products. Accordingly, the applicants have now
identified a novel sunscreen composition that is suitable for use on wet skin and resists the
tendency to whiten in the presence of residual water.
SUMMARY OF THE INVENTION
The present invention relates to substantially anhydrous compositions comprising at
least 10% by weight of a C or C mono-alcohol; an organic UV-filter; and an oil portion
comprising one or more oils. The oil portion is miscible with the C or C mono-alcohol and
has an interfacial tension with water of greater than 9 and less than 32.5. The composition has
a volume fraction of oil portion relative to the sum of the oil portion plus the C or C mono-alcohol
that is greater than 0.33. The compositions include about 1.5% or less by weight of a solid
organic UV-filter.
Accordingly, in a first aspect, the invention provides a composition comprising:
at least 10% by weight of a C or C mono-alcohol;
an organic UV-filter;
an oil portion comprising one or more oils, wherein the oil portion is miscible
with the C or C mono-alcohol, wherein the oil portion has an interfacial tension with water
of greater than 9mN/m and less than 32.5mN/m, and
wherein the composition has a volume fraction of the oil portion relative to the oil portion plus the C
or C mono-alcohol that is about 0.33 or greater, wherein said UV-filter is selected such that
the composition comprises about 1.5% by weight or less of a solid, organic UV-filter
dissolved therein, and wherein the composition comprises less than 1 percent by weight
water.
DETAILED DESCRIPTION OF THE INVENTION
It has been discovered that solid, organic ultraviolet (UV) sunscreen filters can be
dissolved in a composition comprising a C or C mono-alcohol, and an oil portion
comprising one or more oils, to form a substantially anhydrous composition that surprisingly
resists whitening in the presence of water.
As used herein, “cosmetically acceptable” means suitable for use in contact with
tissues (e.g., the skin) without undue toxicity, incompatibility, instability, irritation, allergic
response, or the like.
As used herein, “substantially free” means the composition contains less than about 1,
such as less than about 0.1, e.g., less than about 0.01 weight percent of an ingredient.
Compositions of the present invention are substantially anhydrous. By “substantially
anhydrous” it is meant that the composition is substantially free of water.
Concentration Ranges and “Concentrate”
Unless otherwise specifically described, all percentages included herein are
percentages by weight, based on total weight of the composition, excluding any propellant
that may be present. For compositions that include a propellant, the term “concentrate” is
used to refer to that portion of the composition that excludes propellant.
Organic UV-filter
Compositions of the present invention include an organic UV filter. The organic UV-
filter may be a dissolved, solid, organic UV filter. Solid, organic UV-filters that are useful in
the present invention are cosmetically-acceptable compounds that absorb radiation in the UV
range, are solid at ambient temperature (22 C) and pressure (1 atmosphere), and are generally
soluble in one or more organic hydrocarbon solvents. The organic, UV filter absorbs
radiation in some portion of the ultraviolet spectrum (290nm-400nm), and may have an
-1 -1
extinction coefficient of about 1000 mol cm or more, for example greater than 10,000 or
-1 -1
100,000 or 1,000,000 mol cm , for at least one wavelength within the above-defined
ultraviolet spectrum. The organic UV-filter, which is solid at ambient temperature, is
dissolved and homogeneously distributed in the composition (exclusive of any propellant).
Examples of solid organic UV-filters that may be dissolved in compositions of the
present invention include, without limitation, benzophenone-3 (i.e., oxybenzone), 2-Hydroxy-
4-methoxyphenyl)-(2-hydroxyphenyl)methanone (i.e., dioxybenzone), 2-(2H-Benzotriazol
yl)methylphenol, also known as drometrizole trisiloxane (also known as MEXORYL XL),
butylmethoxy dibenzoylmethane (“avobenzone”), 4-methyl benzilidene camphor (“4-MBC”),
ethylhexyl triazone (available as UVINUL T-150 from BASF of Ludwigshafen, Germany),
diethylamino hydroxybenzoyl hexyl benzoate (“DHHB”) available as UVINUL A Plus from
BASF; and Bemotrizinol (available as TINOSORB S from BASF), Menthyl
aminobenzoate (“menthyl anthranilate”), 4-Aminobenzoic acid (“PABA”), hydroxy
methylphenyl benzotriazole, and combinations thereof.
According to certain embodiments, the solid, organic UV-filters may be selected from
the group consisting of oxybenzone, avobenzone, drometrizole trisiloxane, ethylhexyl
triazone, DHHB, and Bemotrizinol. According to certain other embodiments, the solid,
organic UV-filters are selected from the group consisting of oxybenzone and avobenzone.
According to certain other embodiments, the solid, organic UV-filters used in compositions
of the present invention consist of oxybenzone and avobenzone. According to certain other
embodiments the solid, organic UV-filter includes oxybenzone. The dissolved organic,
UV-filter, if included, is present in a concentration of about 1.5% or less by weight. The
dissolved organic, UV-filter may be present in a concentration range from about 0.5% to
about 1.5.
According to certain embodiments, the organic UV-filter is an organic UV-filter that
is liquid at ambient temperature (22ºC) and pressure (1 atmosphere). Such “liquid, organic
UV-filters” are described below in the section entitled “Oil Portion.”
C or C Mono-alcohol
Compositions of the present invention include a C or C mono-alcohol. By “C or C
2 3 2 3
mono-alcohol” it is meant ethanol, propanol, isopropanol, or combinations thereof. In certain
embodiments the C or C mono-alcohol is ethanol. The C or C mono-alcohol is present in
2 3 2 3
a concentration of about 10% or more by weight. According to certain embodiments, the C
or C mono-alcohol is present in a concentration from about 10% to about 67%, such as from
about 12% to about 67%, such as from about 15% to about 57%, such as from about 20% to
about 57%, e.g., from about 25% to about 55% by weight.
Oil Portion
Compositions of the present invention include an oil portion. By “oil portion,” it is
meant, collectively, all of the oils present in the composition (i.e., no oils present in the
composition are excluded from the oil portion). The oil portion, in aggregate, has a moderate
polarity. As such, the oil portion has an interfacial tension with water that is greater than 9
and less than 32.5. According to certain embodiments of the invention, the oil portion has an
interfacial tension with water that is from about 10 to about 37, such as from about 11.6 to
about 32.5, such as from about 11.6 to about 30, such as from about 11.6 to about 25, e.g.,
from about 11.6 to about 20. According to one embodiment of the invention, the oil portion
of the composition has an interfacial tension with water that is equal to or greater than that of
diisopropyl adipate and equal to or less than that of a C -C alkyl benzoate (Tegosoft TN
12 18
available from Evonik Goldschmidt GmbH of Essen, Germany).
The interfacial tension of the oil portion may be determined by the “Pendant Drop
Interfacial Tension Test,” as described below. A contact angle meter, such as the (Dynamic)
Contact Angle Meter model DM-701, made by Kyowa Interface Science Co., Ltd. (Tokyo,
Japan), equipped with FAMAS interface measurement analysis system software, is used. A
reservoir on the meter is filled with deionized water, and a glass syringe is filled with test oil.
When the oil portion is less dense than the water, an inverted 22-gauge stainless steel needle
is attached to the syringe, from which a small amount of the oil is pushed into the water
reservoir to form a drop at the end of the needle. When the oil portion is denser than the
water, a normal 22-gauge stainless steel needle is used. After the drop is formed at the end of
the needle, sufficient time is given for each drop to reach a point of stability. Once the drop
is stable, images of the drop are captured with a fast image capturing camera (up to 60 frames
per second) and the software calculates the interfacial tension of the oil with water based on
the shape of the drop in the captured image. A new liquid droplet is created for each
measurement. The distilled water medium is changed and the container is cleaned for every
measurement to minimize influence from liquid cross-mixing. The interfacial tension values
are measured in triplicate for each oil sample.
In order to standardize the results and allow for some variance in measurement for the
Pendant Drop Interfacial Tension Test, diisopropyl adipate is assigned a standard interfacial
tension value of 11.6. At the time of each test, diisopropyl adipate is tested to determine the
value of diisopropyl adipate tested vs. the standard interfacial tension for diisopropyl adipate.
If the value for the tested diisopropyl adipate is determined to be different than 11.6, then the
subsequent values for interfacial tension for other oils are adjusted upward or downward for
situations where the value measured for diisopropyl adipate is greater or less than 11.6,
respectively. The adjusting factor is the ratio of the measured value for diisopropyl adipate
divided by 11.6. For example, if diisopropyl adipate is measured at the time as 13.1, then the
reported values will be multiplied by 13.1/11.6, i.e. 1.13.
The oil portion includes one or more oils. By “oil,” it is meant a hydrophobic
compound that has a melting point that is below 30 C and is insoluble in water. Although all
of the one or more oils of the oil portion may be selected to have an interfacial tension with
water that is greater than 9 and less than 32.5, each individual oil present in the oil portion
need not meet this requirement, so long as the oil portion, as a whole, meets the requirement.
The one or more oils may be selected to meet one or more of the following three criteria: (a)
has a carbon chain of at least four carbons in which none of the four carbons is a carbonyl
carbon; (b) has two or more alkyl siloxy groups; or (c) has two or more oxypropylene groups
in sequence. The hydrophobic moiety may include linear, cyclic, aromatic, saturated or
unsaturated groups. According to certain embodiments, compounds that are amphiphilic are
excluded from the definition of “oil” and such compounds that have hydrophilic moieties,
such as anionic, cationic, zwitterionic, or nonionic groups, that are polar, including sulfate,
sulfonate, carboxylate, phosphate, phosphonates, ammonium, including mono-, di-, and
trialkylammonium species, pyridinium, imidazolinium, amidinium, poly(ethyleneiminium),
ammonioalkylsulfonate, ammonioalkylcarboxylate, amphoacetate, and
poly(ethyleneoxy)sulfonyl moieties, are so excluded.
According to certain alternative embodiments, under certain conditions as set forth
below, amphiphilic compounds that otherwise meet the requirements of “oil” as set forth
above are considered “oils,” and therefore are considered to be part of the oil portion.
According to this alternative embodiment, the amphiphilic compounds that otherwise meet
the requirements of “oil” and are not so amphiphilic so as to render the oil portion to be able
to emulsify water. For example, in this alternative embodiment, the oil portion including the
amphiphilic compound is not capable of forming a water-in-oil emulsion (stable for one week
at 20 C) when 1 part by weight of water is added to 2 parts of the oil portion and agitated in a
manner typically suitable for forming a water-in-oil emulsion.
Compounds suitable for use in or as the oil portion include various hydrocarbons
(straight or branched chain alkanes or alkenes, ketone, diketone, primary or secondary
alcohols, aldehydes, sterol esters, alkanoic acids, turpenes, monoesters), such as those having
a carbon chain length ranging from C -C , such as C -C . In one embodiment of the
6 38 6 18
invention, the oils include ester and/or ether functional groups.
Suitable non-limiting examples of oil that may be included in the oil portion are alkyl
diesters. One suitable alkyl diester is diisopropyl adipate, available as CRODAMOL DA
from Croda Inc. of Edison, NJ (CRODAMOL DA has an interfacial tension as measured
using the Pendant Drop Interfacial Tension Test of 11.6). Another suitable class of oils
include the reaction product of glycols and fatty acids. One suitable reaction product of
glycols and fatty acids is PPG-2 myristyl ether propionate available as Crodamol PMP from
Croda Inc. of Edison, NJ (CRODAMOL PMP has an interfacial tension as measured using
the Pendant Drop Interfacial Tension Test of 16.8). Another suitable class of oils includes
triglycerides. One suitable triglyceride is a mixture of caprylic/capric triglycerides, available
as Miglyol 812 from Sasol Olefins & Surfactants of Houston, Texas. Miglyol 812 has an
interfacial tension as measured using the Pendant Drop Interfacial Tension Test of 24.7.
Another suitable class of oils includes alkyl esters. One such suitable alkyl ester is isopropyl
palmitate, available as Propal NF from the Lubrizol Corporation of Wickliffe, Ohio. Another
suitable class of oils includes dialkyl carbonates. One suitable dialkyl carbonate is a
dicaprylyl carbonate, available as CETIOL CC from Cognis Corp. of Ambler, Pennsylvania.
CETIOL CC has an interfacial tension as measured using the Pendant Drop Interfacial
Tension Test of 31.9. Another suitable class of oils includes alkyl benzoate esters. One
suitable alkyl benzoate ester C -C alkyl benzoate, available as FINSOLV TN (CAS#
12 15
684118, specific gravity 0.915-0.935; refractive index at 20C 1.43-1.487) from Innospec
Active Chemicals of Edison, New Jersey, or Tegosoft TN from Evonik Goldschmidt GmbH
of Essen, Germany. Tegosoft TN has an interfacial tension as measured using the Pendant
Drop Interfacial Tension Test of 32.5.
As mentioned above, certain oils that have interfacial tension with water outside the
ranges noted above (e.g., greater than 9 and less than 32.5) may be included in the oil portion
as long as a sufficient percentage of the oil portion is formed from oils within the noted
ranges. However, it is not suitable for the oil portion to consist entirely of oils having
interfacial tension with water of 9 or less, or to include such oils at levels effective to lower
the interfacial tension of the aggregate oil portion to less than 9. Similarly, it is not suitable
for the oil portion to consist entirely of oils having interfacial tension with water of 32.5 or
more, or to include such oils at levels effective to raise the interfacial tension of the aggregate
oil portion to greater than 32.5.
Examples of oils having an interfacial tension with water of 9 or less include a blend
of C -C alkyl benzoate, dipropylene glycol dibenzoate, and PPG-15 stearyl ether benzoate,
12 15
available as FINSOLV TPP from Innospec Active Chemicals. Examples of oils having an
interfacial tension with water of 32.5 or more, include C12-C15 Alkyl Benzoate (interfacial
tension, I.T. = 32.5, as measured by applicants), dimethicone (interfacial tension, I.T. = 45, as
reported in K. Hughes, Vadim F. Lvovich, J. Woo, B.Moran, A.Suares, M.Truong, “Novel
methods for emollient characterization”, Cosmetics and Toiletries Manufacture Worldwide,
2006, 19-24), ethyl methicone (I.T. = 46.3, as measured by the applicants),
diethylhexylcyclohexane available as CETIOL S from Cognis (I.T. = 49.8), and mineral oil
(I.T. = 50, again as reported in K. Hughes, Vadim F. Lvovich, J. Woo, B.Moran, A.Suares,
M.Truong, “Novel methods for emollient characterization”, Cosmetics and Toiletries
Manufacture Worldwide, 2006, 19-24).
Other oils suitable for use in the composition are organic UV-filters that are liquid at
ambient temperature (22ºC) and pressure (1 atmosphere). Liquid, organic UV-filters that are
useful in the present invention are cosmetically-acceptable compounds that absorb radiation
in the UV range and are generally soluble in one or more organic hydrocarbon solvents. The
organic, UV-filter absorbs radiation in some portion of the ultraviolet spectrum (290nm-
-1 -1
400nm), and may have an extinction coefficient of at least about 1000 mol cm , for
-1 -1
example greater than 10,000 or 100,000 or 1,000,000 mol cm , for at least one wavelength
within the above-defined ultraviolet spectrum. According to certain embodiments, the liquid,
organic UV-filter co-exists with the oil portion and the C -C mono-alcohol in a single phase.
Examples of liquid, organic UV-filters include, without limitation, esters of
cinnamonic acid, in particular 4-methoxycinnamonic acidethylhexylester, 4-
methoxycinnamonicacid propylester, 4-methoxycinnamic acid isoamyl ester, 2-cyano-3,3-
phenylcinnamonic acidethylhexyl ester (octocrylene); esters of salicylic acid, i.e., salicylic
acidethylhexylester, salicylic acidisopropylbenzyl ester, salicylic acid homomenthyl
ester, 3,3,5-Trimethylcyclohexyl 2-hydroxybenzoate (homosalate), dimethicodiethyl benzal
malonate, and Polysilicone-15.
As one skilled in the art will readily appreciate, the term “organic UV-filter”, as used
herein, does not include ultraviolet-screening particles (“UV-screening particles”) typically
used at least in part to scatter ultraviolet radiation. Examples of UV-screening particles
include inorganic oxides, including titanium dioxide, zinc oxide, iron oxides, silicone oxides,
or other metal (e.g., transition metal, such as crystalline transition metal) oxides. As one
skilled in the art will also readily appreciate, the term “solid, organic UV-filter”, as used
herein, does not include particulate organic UV-filters (e.g., such as particulate Bisoctrizole,
available as TINOSORB M from BASF) that exist as dispersions of the solid particles in the
composition (typically white in appearance), as opposed to compositions of the present
invention where the UV-filter is dissolved in the composition. According to certain
embodiments of the invention, composition of the present invention are substantially free of
one or both of UV-screening particles and particulate organic UV-filters that exist as
dispersions in the composition. In other embodiments the compositions of the invention are
free of such UV-screening particles and particulate organic UV-filters.
The liquid, organic, UV-filter may be present in the composition, or concentrate, in a
range from about 0% to about 40%, such as from about 5% to about 35%, such as from about
% to about 35%, e.g., from about 15% to about 35% by weight.
The oil portion may be present in the composition, or concentrate, in a range from
about 8% to about 90%, such as from about 20% to about 75%, such as from about 30% to
about 65%, e.g., from about 40% to about 55% by weight.
Furthermore, the inventors have found that it is necessary that compositions of the
present invention have a sufficient amount of oil portion relative to the amount of C or C
mono-alcohol. The volume fraction of oil relative to the sum of oil plus the C or C mono-
alcohol (V ) is calculated by dividing the volume percentage of the oil portion in the
composition, or concentrate, by the sum of the volume of the oil portion and the volume of
the C or C mono-alcohol.
Specifically, V should be about 0.33 or greater. According to certain embodiments
of the invention, V is from 0.33 to about 0.9, such as from about 0.33 to about 0.89, such as
from about 0.40 to about 0.85, such as from about 0.40 to about 0.80. According to certain
embodiments, such as when a film-forming polymer that is insoluble in the oil portion but is
soluble in the C or C mono-alcohol is present in the composition, V may be greater than
2 3 oil
0.50 and less than about 0.80, such as from 0.53 to about 0.65.
Other Ingredients
Compositions of the present invention may include a film forming polymer to
enhance film formation and provide some water resistance. By “film-forming polymer,” it is
meant a polymer that, when dissolved in the composition, permits a continuous or semi-
continuous film to be formed when the composition is spread onto, e.g., smooth glass, and the
liquid vehicle is allowed to evaporate. As such, the polymer should dry on the glass in a
manner in which it should be predominantly continuous over the area upon which it is spread,
rather than forming a plurality of discrete, island-like structures. Generally, the films formed
by applying compositions on the skin according to embodiments of the invention described
herein, are less than, on average, about 100 microns in thickness, such as less than about 50
microns. In certain embodiments, the film-forming polymer is insoluble in the oil portion
(i.e., is oil-insoluble), but is soluble in the C or C mono-alcohol.
Suitable film-forming polymers include natural polymers such as polysaccharides or
proteins and synthetic polymers such as polyesters, polyacrylics, polyurethanes, vinyl
polymers, polysulfonates, polyureas, polyoxazolines, and the like. Specific examples of film-
forming polymers include, for example, acrylic homopolymers or copolymers with
hydrophobic groups, such as acrylate/ocylacrylamide copolymers, including DERMACRYL
79, available from Akzo Chemical of Bridgewater, New Jersey; dimethicone/acrylates
dimethicone copolymer, available as X8247D from Shin-Etsu of Japan; hydrogenated
dimer dilinoleyl/dimethylcarbonate copolymer, available from Cognis Corporation of
Ambler, Pennsylvania as COSMEDIA DC; copolymer of vinylpyrrolidone and a long-chain
alpha-olefin, such as those commercially available from ISP Specialty Chemicals of Wayne,
New Jersey as GANEX V220; vinylpyrrolidone/tricontanyl copolymers available as GANEX
WP660 also from ISP; water-dispersible polyesters, including sulfopolyesters such those
commercially available from Eastman Chemical as EASTMAN AQ 38S. In certain
embodiments, the film-forming polymer is water-insoluble, but is rendered soluble upon
exposure to alkalinity in order to facilitate removal from the skin upon washing with soap.
The amount of film-forming polymer present in the concentrate may be from about 0.25% to
about 15%, or from about 0.5% to about 10%, or from about 1% to about 5%.
In certain embodiments, the composition includes a wax. By wax, it is meant one or
more hydrophobic compounds that have a melting point (or melting range) that is in the range
◦ ◦ ◦ ◦
from 30 C to 120 C, such as in the range from 45 C to 100 C. In one embodiment, the wax
component includes a wax compound having a melting point from about 75 C to 100 C.
Suitable waxes include any of various hydrocarbons (straight or branched chain
alkanes or alkenes, ketone, diketone, primary or secondary alcohols, aldehydes, sterol esters,
alkanoic acids, turpenes, monoesters), such as those having a carbon chain length ranging
from C -C . Also suitable are diesters or other branched esters. In one embodiment, the
12 38
compound is an ester of an alcohol (glycerol or other than glycerol) and a C or greater fatty
acid.
Non-limiting examples include any of various natural waxes including lotus wax (e.g.,
Nelumbo Nucifera Floral Wax available from Deveraux Specialties, Silmar, California);
beeswax (e.g., White Beeswax SP-422P available from Strahl and Pitsch of West Babylon,
New York), insect waxes, sperm whale oil, lanolin, vegetable waxes such as canauba wax,
jojoba oil, candelilla wax; mineral waxes such as paraffin wax; and synthetic waxes such as
cetyl palmitate, lauryl palmitate, cetostearyl stearate, and polyethylene wax (e.g.,
PERFORMALENE 400, having a molecular weight of 450 and a melting point of 84 C,
available from New Phase Technologies of Sugar Land, Texas); and silicone waxes such as
C Alkyl Methicone and C Olefin (e.g., Dow Corning AMS-C30, having a melting
-45 30-45
point of 70 C, available from Dow Corning of Midland, Michigan). In certain embodiments,
the wax component includes a high melting point ester of glycerol such as glycerol
monostearate. The amount of wax may be present in the composition from about 0.1% to
about 5%, or from about 0.1% to about 2%, or from about 0.1% to about 1%.
Any of various other cosmetically-acceptable ingredients may be included in the
composition in amounts so as to not counter the effects of the various other ingredients. For
example, ingredients such as fragrances, dyes, preservatives, skin benefit agents,
photostabilizers, anti-oxidants may be includes, in, for example total concentrations that are
less than about 10%, such as less than about 5%, such as about 2% or less, e.g., less than
about 1%.
Compositions of the present invention are generally provided in the form of a single
phase solution of various ingredients in the C or C mono-alcohol. The single phase solution
may be prepared using techniques known in the art, such as by charging a vessel with C or
C mono-alcohol and sequentially mixing/dissolving the various ingredients therein.
Compositions of the present invention may be included as a concentrate in a product that
additionally includes a propellant. The optional propellant generally exists as a vapor in
equilibrium with liquid propellant that is dissolved in or is miscible with the remainder of the
composition. The optional propellant aids in spraying the composition onto the skin. One
suitable propellant is isobutene. According to another embodiment of the invention, the
propellant has finite (non-zero) solubility in water. Suitable examples of such propellants are
dimethyl ether (which has a water solubility of 71 g/liter at 20 °C) and methyl ethyl ether.
The aerosol propellant may comprise about 10% to about 60%, or from about 20% to
about 40%, or from about 25% to about 40% of the total weight of the concentrate plus
propellant. In an alternative embodiment, rather than include a conventional aerosol
propellant, the composition may be propelled without ejected propellant using a “bag on
valve” system which utilizes air or nitrogen that is isolated from the remainder of the
composition. In use, compositions of the present invention are applied to skin, such as wet
skin, and optionally rubbed onto the skin, in order to provide a protective UV sun-screening
composition thereon.
EXAMPLES
The following non-limiting examples further illustrate the claimed invention:
Example I: Interfacial Tension Measurements and Ethanol Miscibility
Interfacial tension with water and ethanol miscibility were evaluated for a variety of
cosmetic (emollient) oils as well as a mixture of liquid, organic UV-filters. Interfacial
tension with water was evaluated using the Pendant Drop Interfacial Tension Test, as
described above. Miscibility with ethanol was evaluated by visual examination of the oil
ethanol mixtures. Oil/ethanol mixtures that separated into two phases after about one week
exhibited a hazy or milky appearance when shaken due to the formation of an emulsion were
considered to be immiscible. If the mixtures were clear, they were considered to be miscible.
The results are reported in Table 1, below.
Table 1: Interfacial Tension and Ethanol Miscibility of Oils
Interfacial Tension, Interfacial Tension, Miscibility with
Mean Std Deviation Ethanol
(mN/m)
FINSOLV TPP 9 --- Yes
CRODAMOL DA 11.6 0.1 Yes
PPGMyristyl 16.8 0.1 Yes
Ether Propionate
Caprylic/Capric 24.7 0.2 Yes
Triglycerides
Isopropyl Palmitate 28.6 0.1 Yes
Cetiol CC 31.9 0.3 Yes
C -C alkyl 32.5 0.1 Yes
12 15
benzoate
CETIOL S 49.8 0.5 No
Oil blend, organic 22.9 0.1 Yes
UV-filters and other
oils
FINSOLV TPP was not measured for interfacial tension, but rather the data was taken from the supplier
(Innospec) product literature.
The oil blend, organic UV-filters and other oils, is a mixture that consisted of 3 liquid, organic UV-filters and
2 other oils – specifically; Homosalate;, Octisalate:, Octocrylene:, Butyloctyl Salicylate:, Corpan TQ, in a
weight ratio of 15:5:10:5:0.1, respectively.
From the results, it can be noted that only the oil with the highest interfacial tension
(Cetiol S) was not miscible with ethanol.
Example II: Effect of V and Interfacial Tension on Whitening: 0.5% Avobenzone, 1.5%
Oxybenzone
The effect of interfacial tension of various oils, as well as the volume fraction oil
relative to oil plus ethanol (V ), were evaluated for effect on whitening in the presence of
water. In order to facilitate sample preparation, two stock solutions were prepared:
Stock Solution 1: A solution of 0.5% avobenzone + 1% oxybenzone was prepared in ethanol
and heated as needed to solubilize the solid, organic UV-filters.
Stock Solution 2: A solution of 0.5% avobenzone + 1% oxybenzone was prepared in each of
the various oils to be tested and again heated as needed to solubilize the solid, organic UV-
filters.
The stock solutions 1 and 2 were mixed in different volume proportions of Stock 1:
Stock 2, to create mixtures with a calculated oil/oil+ethanol ratio (V ) values listed in the
first column of Table 2, below. As such, all compositions included 0.5% avobenzone and 1%
oxybenzone. Each composition included a mixture of ethanol with one oil, wherein the V
ranged from 0.091 to 0.91. Seven specific values for V were tested for five different oils.
Thus thirty-five (i.e., (7x5) different compositions were evaluated.
Each of the mixtures was evaluated for whitening with a “Water Drop Whitening
Test,” whereby a 20 microliter drop of DI water is placed onto a smooth, black, flat, non-
porous, hydrophobic surface that has been pre-cleaned with ethanol. A 20 microliter drop of
the sample product is then added to the water droplet. The intensity of whiteness in the final
drop is scored by visual inspection on a pass/fail scale, where pass (P) is clear like an oil
drop, or very slightly hazy and fail (F) is whitening like a drop of skim milk at a dilution of
up to 95% in water. The nineteen compositions with a score of P are Inventive examples.
The sixteen compositions with a score of F are Comparative examples. The results are shown
in Table 2, below:
Table 2: Water Drop Whitening Test Results: 0.5% Avobenzone Plus 1% Oxybenzone
V PPG-2 Caprylyl Isopropyl Dacaprylyl C -C
oil 12 18
Myristyl Capric palmitate carbonate Alkyl
Ether Triglycerides Benzoate
Propionate
16.8 24.7 28.6 31.9 32.5
0.91 P P P P P
0.80 P P P P P
0.50 P P P P P
0.40 P P P P F
0.33 F F F F F
0.20 F F F F F
0.091 F F F F F
Example III: Effect of V and Interfacial Tension on Whitening: 3% Avobenzone, 6%
Oxybenzone
An experiment similar to the one described above for Example II was performed,
except that the solid, organic UV-filter was 6% oxybenzone and 3% avobenzone. Two
additional levels of V were tested for three of the oils (PPG-2 Myristyl Ether Propionate,
Dacaprylyl carbonate, and C -C Alkyl Benzoate). As such forty-eight compositions were
12 18
tested. These forty-eight examples have levels of solid, organic UV-filter that are greater
than 1.5%. The results are shown in Table 3, below:
Table 3: Water Drop Whitening Test Results: 3% Avobenzone Plus 6% Oxybenzone
V Finsolv PPG-2 Caprylyl Isopropyl Dacaprylyl C -C
oil 12 18
TPP Myristyl Capric palmitate carbonate Alkyl
Ether Triglycerides Benzoate
Propionate
9.0 16.8 24.7 28.6 31.9 32.5
0.91 F P P P P P
0.80 F P P P P P
0.50 F P P P P P
0.47 P P F
0.43 F F F
0.40 F F F F F F
0.33 F F F F F F
0.20 F F F F F F
0.091 F F F F F F
Example IV: Effect of V and Interfacial Tension on Whitening: 3% Oxybenzone
An experiment similar to the one described above for Example I was performed,
except that the solid, organic UV-filter was 3% oxybenzone and no avobenzone. These thirty
five examples have levels of solid, organic UV-filter that are greater than 1.5%. The results
are shown in Table 4, below:
Table 4: Water Drop Whitening Test Results: 3% Oxybenzone
V PPG-2 Caprylyl Isopropyl Dacaprylyl C -C
oil 12 18
Myristyl Capric palmitate carbonate Alkyl
Ether Triglycerides Benzoate
Propionate
16.8 24.7 28.6 31.9 32.5
0.91 P P P P P
0.80 P P P P P
0.50 P P P P P
0.40 F F F F F
0.33 F F F F F
0.20 F F F F F
0.091 F F F F F
It can be seen from the above results that by selecting levels of solid organic UV-filter
that are up to about 1.5% by weight (see Example I), one can expand the range of
compositions (e.g., the range of V ) that resist whitening in the presence of water.
Claims (20)
1. A composition comprising: at least 10% by weight of a C or C mono-alcohol; an organic UV-filter; an oil portion comprising one or more oils, wherein the oil portion is miscible with the C or C mono-alcohol, wherein the oil portion has an interfacial tension with water of greater than 9mN/m and less than 32.5mN/m, and wherein the composition has a volume fraction of the oil portion relative to the oil portion plus the C or C mono-alcohol that is about 0.33 or greater, wherein said UV-filter is selected such that the composition comprises about 1.5% by weight or less of a solid, organic UV-filter dissolved therein, and wherein the composition comprises less than 1 percent by weight water.
2. The composition of claim 1, wherein the composition comprises 10% to about 67% of the C or C mono-alcohol.
3. The composition of claim 1, wherein the composition comprises 15% to about 57% of the C or C mono-alcohol.
4. The composition of claim 1, wherein the composition comprises 20% to about 57% of the C or C mono-alcohol.
5. The composition of claim 1, wherein the oil portion has an interfacial tension with water of from about 11.6mN/m to about 32.5mN/m.
6. The composition of claim 1, wherein the oil portion has an interfacial tension with water that is equal to or greater than that of diisopropyl adipate and equal to or less than that of C -C alkyl benzoate. 12 15
7. The composition of claim 1, wherein the oil portion has an interfacial tension with water of from about 11.6mN/m to about 30mN/m.
8. The composition of claim 1, wherein the oil portion has an interfacial tension with water of from about 11.6mN/m to about 25mN/m.
9. The composition of claim 1, wherein the oil portion has an interfacial tension with water of from about 11.6mN/m to about 20mN/m.
10. The composition of claim 1, wherein the volume fraction of the oil portion relative to the oil portion plus the C or C mono-alcohol is from about 0.33 to about 0.90.
11. The composition of claim 1, wherein the volume fraction of oil relative to oil plus C or C mono-alcohol is from greater than 0.40 and less than about 0.80.
12. The composition of claim 1, wherein the volume fraction of oil relative to oil plus C or C mono-alcohol is from about 0.53 to about 0.65.
13. The composition of claim 11, wherein the composition comprises an oil-insoluble, film-forming polymer.
14. The composition of claim 12, wherein the composition comprises an oil-insoluble, film-forming polymer.
15. The composition of claim 1, wherein the solid organic UV-filter is selected from the group consisting of avobenzone and oxybenzone.
16. The composition of claim 1, wherein the solid organic UV-filter comprises about 1 % or less of oxybenzone.
17. The composition of claim 1, wherein the composition comprises from about 0.5% to about 1.5% of the solid, organic UV-filter dissolved therein.
18. The composition of claim 1, wherein the oil portion comprises a liquid, organic UV- filter.
19. The composition of claim 1, wherein the one or more oils have a carbon chain of at least four carbons in which none of the four carbons is a carbonyl carbon.
20. A composition according to any one of the preceding claims substantially as herein described with reference to any example thereof.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/246,972 | 2011-09-28 | ||
US13/246,972 US20130078199A1 (en) | 2011-09-28 | 2011-09-28 | Topical sunscreen compositions |
Publications (2)
Publication Number | Publication Date |
---|---|
NZ602661A NZ602661A (en) | 2014-02-28 |
NZ602661B true NZ602661B (en) | 2014-06-04 |
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ID=
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