WO2024028514A1 - Composition ayant un facteur de protection solaire amélioré et une photoprotection contre les uva améliorée - Google Patents
Composition ayant un facteur de protection solaire amélioré et une photoprotection contre les uva améliorée Download PDFInfo
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- WO2024028514A1 WO2024028514A1 PCT/EP2023/071792 EP2023071792W WO2024028514A1 WO 2024028514 A1 WO2024028514 A1 WO 2024028514A1 EP 2023071792 W EP2023071792 W EP 2023071792W WO 2024028514 A1 WO2024028514 A1 WO 2024028514A1
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- Prior art keywords
- substituted
- unsubstituted
- alkyl
- methyl
- group
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- 230000003711 photoprotective effect Effects 0.000 title claims abstract description 39
- 239000000203 mixture Substances 0.000 title claims description 106
- -1 amino acid compound Chemical class 0.000 claims abstract description 403
- 239000000047 product Substances 0.000 claims abstract description 215
- 239000004904 UV filter Substances 0.000 claims abstract description 170
- 239000000516 sunscreening agent Substances 0.000 claims abstract description 134
- 230000000475 sunscreen effect Effects 0.000 claims abstract description 133
- 239000002537 cosmetic Substances 0.000 claims abstract description 116
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 103
- 230000004224 protection Effects 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- 230000008901 benefit Effects 0.000 claims abstract description 7
- 230000009759 skin aging Effects 0.000 claims abstract description 7
- 230000002087 whitening effect Effects 0.000 claims abstract description 7
- 230000003712 anti-aging effect Effects 0.000 claims abstract description 6
- 208000019000 darkening of skin Diseases 0.000 claims abstract description 6
- 230000003467 diminishing effect Effects 0.000 claims abstract description 6
- 230000002708 enhancing effect Effects 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 314
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 208
- 125000000217 alkyl group Chemical group 0.000 claims description 171
- 239000000049 pigment Substances 0.000 claims description 171
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 164
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 135
- 150000001875 compounds Chemical class 0.000 claims description 127
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 94
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 83
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 82
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 claims description 82
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 81
- 229910000420 cerium oxide Inorganic materials 0.000 claims description 81
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 81
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 claims description 81
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 81
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 81
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 72
- 125000001072 heteroaryl group Chemical group 0.000 claims description 71
- 150000001408 amides Chemical class 0.000 claims description 63
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 63
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 63
- 229910052739 hydrogen Inorganic materials 0.000 claims description 63
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 63
- 239000003921 oil Substances 0.000 claims description 63
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 61
- 125000001424 substituent group Chemical group 0.000 claims description 61
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 56
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 125000004414 alkyl thio group Chemical group 0.000 claims description 48
- 239000000377 silicon dioxide Substances 0.000 claims description 47
- 125000003545 alkoxy group Chemical group 0.000 claims description 46
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 45
- 239000003795 chemical substances by application Substances 0.000 claims description 44
- 229910052710 silicon Inorganic materials 0.000 claims description 43
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 42
- 239000010703 silicon Substances 0.000 claims description 42
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 claims description 41
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 235000012239 silicon dioxide Nutrition 0.000 claims description 41
- 229960001866 silicon dioxide Drugs 0.000 claims description 40
- 125000003342 alkenyl group Chemical group 0.000 claims description 39
- 125000000304 alkynyl group Chemical group 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- 229910052760 oxygen Inorganic materials 0.000 claims description 32
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 30
- 239000000126 substance Substances 0.000 claims description 27
- 125000002252 acyl group Chemical group 0.000 claims description 26
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 125000003107 substituted aryl group Chemical group 0.000 claims description 20
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 18
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 18
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 18
- 239000000839 emulsion Substances 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 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 claims description 11
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 10
- 238000009472 formulation Methods 0.000 claims description 10
- 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 claims description 9
- WSSJONWNBBTCMG-UHFFFAOYSA-N 2-hydroxybenzoic acid (3,3,5-trimethylcyclohexyl) ester Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C1=CC=CC=C1O WSSJONWNBBTCMG-UHFFFAOYSA-N 0.000 claims description 9
- 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 claims description 9
- WYWZRNAHINYAEF-UHFFFAOYSA-N Padimate O Chemical compound CCCCC(CC)COC(=O)C1=CC=C(N(C)C)C=C1 WYWZRNAHINYAEF-UHFFFAOYSA-N 0.000 claims description 9
- 239000013543 active substance Substances 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 claims description 8
- 150000001413 amino acids Chemical class 0.000 claims description 8
- UVCJGUGAGLDPAA-UHFFFAOYSA-N ensulizole Chemical compound N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 UVCJGUGAGLDPAA-UHFFFAOYSA-N 0.000 claims description 8
- 229960000655 ensulizole Drugs 0.000 claims description 8
- 229960004881 homosalate Drugs 0.000 claims description 8
- 229960001679 octinoxate Drugs 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 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 claims description 7
- 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 claims description 7
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical group C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 7
- UBNYRXMKIIGMKK-RMKNXTFCSA-N amiloxate Chemical compound COC1=CC=C(\C=C\C(=O)OCCC(C)C)C=C1 UBNYRXMKIIGMKK-RMKNXTFCSA-N 0.000 claims description 7
- 229960005193 avobenzone Drugs 0.000 claims description 7
- 229960004697 enzacamene Drugs 0.000 claims description 7
- 229940068171 ethyl hexyl salicylate Drugs 0.000 claims description 7
- 210000004209 hair Anatomy 0.000 claims description 7
- 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 claims description 7
- 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 claims description 7
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- 241000723346 Cinnamomum camphora Species 0.000 claims description 6
- 239000004599 antimicrobial Substances 0.000 claims description 6
- 239000003963 antioxidant agent Substances 0.000 claims description 6
- XVAMCHGMPYWHNL-UHFFFAOYSA-N bemotrizinol Chemical compound OC1=CC(OCC(CC)CCCC)=CC=C1C1=NC(C=2C=CC(OC)=CC=2)=NC(C=2C(=CC(OCC(CC)CCCC)=CC=2)O)=N1 XVAMCHGMPYWHNL-UHFFFAOYSA-N 0.000 claims description 6
- 229960001716 benzalkonium Drugs 0.000 claims description 6
- CYDRXTMLKJDRQH-UHFFFAOYSA-N benzododecinium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 CYDRXTMLKJDRQH-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- 229960000846 camphor Drugs 0.000 claims description 6
- 229930008380 camphor Natural products 0.000 claims description 6
- 239000000969 carrier Substances 0.000 claims description 6
- FDATWRLUYRHCJE-UHFFFAOYSA-N diethylamino hydroxybenzoyl hexyl benzoate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1O FDATWRLUYRHCJE-UHFFFAOYSA-N 0.000 claims description 6
- 229960001630 diethylamino hydroxybenzoyl hexyl benzoate Drugs 0.000 claims description 6
- 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 claims description 6
- 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 claims description 6
- 229960000601 octocrylene Drugs 0.000 claims description 6
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 claims description 6
- 229960001173 oxybenzone Drugs 0.000 claims description 6
- 229960000368 sulisobenzone Drugs 0.000 claims description 6
- CENPSTJGQOQKKW-UHFFFAOYSA-N 2,4,6-tris(4-phenylphenyl)-1,3,5-triazine Chemical compound C1=CC=CC=C1C1=CC=C(C=2N=C(N=C(N=2)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 CENPSTJGQOQKKW-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 5
- 239000003752 hydrotrope Substances 0.000 claims description 5
- 239000006210 lotion Substances 0.000 claims description 5
- 239000003771 matrix metalloproteinase inhibitor Substances 0.000 claims description 5
- 229940121386 matrix metalloproteinase inhibitor Drugs 0.000 claims description 5
- 230000003020 moisturizing effect Effects 0.000 claims description 5
- 229940100498 polysilicone-15 Drugs 0.000 claims description 5
- 229920002282 polysilicones-15 Polymers 0.000 claims description 5
- 230000032683 aging Effects 0.000 claims description 4
- 239000002738 chelating agent Substances 0.000 claims description 4
- 239000002826 coolant Substances 0.000 claims description 4
- HEAHZSUCFKFERC-UHFFFAOYSA-N ecamsule Chemical compound CC1(C)C2CCC1(CS(O)(=O)=O)C(=O)C2=CC(C=C1)=CC=C1C=C1C(=O)C2(CS(O)(=O)=O)CCC1C2(C)C HEAHZSUCFKFERC-UHFFFAOYSA-N 0.000 claims description 4
- 239000003995 emulsifying agent Substances 0.000 claims description 4
- 239000006260 foam Substances 0.000 claims description 4
- 239000003205 fragrance Substances 0.000 claims description 4
- 230000001965 increasing effect Effects 0.000 claims description 4
- 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 claims description 4
- 229960002248 meradimate Drugs 0.000 claims description 4
- 239000003755 preservative agent Substances 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- 229940015975 1,2-hexanediol Drugs 0.000 claims description 3
- 229940031723 1,2-octanediol Drugs 0.000 claims description 3
- MEZZCSHVIGVWFI-UHFFFAOYSA-N 2,2'-Dihydroxy-4-methoxybenzophenone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1O MEZZCSHVIGVWFI-UHFFFAOYSA-N 0.000 claims description 3
- ORWUQAQITKSSRZ-UHFFFAOYSA-N 2-hydroxyethyl 4-[bis[2-(2-hydroxyethoxy)ethyl]amino]benzoate Chemical compound OCCOCCN(CCOCCO)C1=CC=C(C(=O)OCCO)C=C1 ORWUQAQITKSSRZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000004129 EU approved improving agent Substances 0.000 claims description 3
- 102000003566 TRPV1 Human genes 0.000 claims description 3
- 101150016206 Trpv1 gene Proteins 0.000 claims description 3
- ZUZFYDYPRGBMKI-UHFFFAOYSA-N [6-[4-[2-benzoyl-4-(diethylamino)-3-hydroxybenzoyl]piperazine-1-carbonyl]-3-(diethylamino)-2-hydroxyphenyl]-phenylmethanone Chemical compound C(C)N(CC)C1=C(C(=C(C(=O)N2CCN(CC2)C(C2=C(C(=C(C=C2)N(CC)CC)O)C(C2=CC=CC=C2)=O)=O)C=C1)C(C1=CC=CC=C1)=O)O ZUZFYDYPRGBMKI-UHFFFAOYSA-N 0.000 claims description 3
- 239000005557 antagonist Substances 0.000 claims description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 3
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 3
- 239000006071 cream Substances 0.000 claims description 3
- YSRSBDQINUMTIF-UHFFFAOYSA-N decane-1,2-diol Chemical compound CCCCCCCCC(O)CO YSRSBDQINUMTIF-UHFFFAOYSA-N 0.000 claims description 3
- 239000006185 dispersion Substances 0.000 claims description 3
- GCXZDAKFJKCPGK-UHFFFAOYSA-N heptane-1,2-diol Chemical compound CCCCCC(O)CO GCXZDAKFJKCPGK-UHFFFAOYSA-N 0.000 claims description 3
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 claims description 3
- AEIJTFQOBWATKX-UHFFFAOYSA-N octane-1,2-diol Chemical compound CCCCCCC(O)CO AEIJTFQOBWATKX-UHFFFAOYSA-N 0.000 claims description 3
- 239000002674 ointment Substances 0.000 claims description 3
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 claims description 3
- 239000002304 perfume Substances 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 238000000518 rheometry Methods 0.000 claims description 3
- 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 claims description 3
- 239000007921 spray Substances 0.000 claims description 3
- 235000010654 Melissa officinalis Nutrition 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- 230000000844 anti-bacterial effect Effects 0.000 claims description 2
- 230000000845 anti-microbial effect Effects 0.000 claims description 2
- 230000001857 anti-mycotic effect Effects 0.000 claims description 2
- 239000002543 antimycotic Substances 0.000 claims description 2
- 229940125904 compound 1 Drugs 0.000 claims description 2
- 239000010408 film Substances 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 239000002502 liposome Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- UEVAMYPIMMOEFW-UHFFFAOYSA-N trolamine salicylate Chemical compound OCCN(CCO)CCO.OC(=O)C1=CC=CC=C1O UEVAMYPIMMOEFW-UHFFFAOYSA-N 0.000 claims description 2
- XMTUJCWABCYSIV-UHFFFAOYSA-N octane-2,3-diol Chemical compound CCCCCC(O)C(C)O XMTUJCWABCYSIV-UHFFFAOYSA-N 0.000 claims 4
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 claims 2
- 230000001476 alcoholic effect Effects 0.000 claims 2
- IEDBILRXQWOCMP-UHFFFAOYSA-N decane-2,3-diol Chemical compound CCCCCCCC(O)C(C)O IEDBILRXQWOCMP-UHFFFAOYSA-N 0.000 claims 2
- ZITKDVFRMRXIJQ-UHFFFAOYSA-N dodecane-1,2-diol Chemical compound CCCCCCCCCCC(O)CO ZITKDVFRMRXIJQ-UHFFFAOYSA-N 0.000 claims 2
- FQJAELSIKLYPGN-UHFFFAOYSA-N dodecane-2,3-diol Chemical compound CCCCCCCCCC(O)C(C)O FQJAELSIKLYPGN-UHFFFAOYSA-N 0.000 claims 2
- VUVZASHBYYMLRC-UHFFFAOYSA-N heptane-2,3-diol Chemical compound CCCCC(O)C(C)O VUVZASHBYYMLRC-UHFFFAOYSA-N 0.000 claims 2
- QCIYAEYRVFUFAP-UHFFFAOYSA-N hexane-2,3-diol Chemical compound CCCC(O)C(C)O QCIYAEYRVFUFAP-UHFFFAOYSA-N 0.000 claims 2
- LJZULWUXNKDPCG-UHFFFAOYSA-N nonane-1,2-diol Chemical compound CCCCCCCC(O)CO LJZULWUXNKDPCG-UHFFFAOYSA-N 0.000 claims 2
- XZSNTZYKCRWZMS-UHFFFAOYSA-N nonane-2,3-diol Chemical compound CCCCCCC(O)C(C)O XZSNTZYKCRWZMS-UHFFFAOYSA-N 0.000 claims 2
- XLMFDCKSFJWJTP-UHFFFAOYSA-N pentane-2,3-diol Chemical compound CCC(O)C(C)O XLMFDCKSFJWJTP-UHFFFAOYSA-N 0.000 claims 2
- 210000004761 scalp Anatomy 0.000 claims 2
- BUMVVNKGNPPUME-UHFFFAOYSA-N undecane-1,2-diol Chemical compound CCCCCCCCCC(O)CO BUMVVNKGNPPUME-UHFFFAOYSA-N 0.000 claims 2
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- 239000011732 tocopherol Substances 0.000 description 1
- 229940042585 tocopherol acetate Drugs 0.000 description 1
- 125000002640 tocopherol group Chemical class 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229940025703 topical product Drugs 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
- ZCIHMQAPACOQHT-ZGMPDRQDSA-N trans-isorenieratene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/c1c(C)ccc(C)c1C)C=CC=C(/C)C=Cc2c(C)ccc(C)c2C ZCIHMQAPACOQHT-ZGMPDRQDSA-N 0.000 description 1
- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
- LOIYMIARKYCTBW-UHFFFAOYSA-N trans-urocanic acid Natural products OC(=O)C=CC1=CNC=N1 LOIYMIARKYCTBW-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 229940094871 trimethoxycaprylylsilane Drugs 0.000 description 1
- OYOGCAUNFUJOMO-UHFFFAOYSA-N trimethyl(octyl)silane Chemical compound CCCCCCCC[Si](C)(C)C OYOGCAUNFUJOMO-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 229960004799 tryptophan Drugs 0.000 description 1
- 235000013976 turmeric Nutrition 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 229940040064 ubiquinol Drugs 0.000 description 1
- QNTNKSLOFHEFPK-UPTCCGCDSA-N ubiquinol-10 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC QNTNKSLOFHEFPK-UPTCCGCDSA-N 0.000 description 1
- 229940035936 ubiquinone Drugs 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229940045136 urea Drugs 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical class [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/27—Zinc; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/29—Titanium; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
Definitions
- the present invention relates to sunscreen products, cosmetic or pharmaceutical preparations or homecare products having UVA and/or UVB protection comprising an inorganic UV-filter and a certain mycosporine-like amino acid compound.
- the products and preparations provide improved SPF performance and UVA photoprotection.
- the products and preparations according to the present invention provide broad- spectrum photo-protection from UV radiation.
- the present invention relates to the use of such mycosporine-like amino acid compound for boosting SPF and UVA photoprotection of a sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprising an inorganic UV-filter.
- the present invention relates to a method of enhancing the SPF and UVA photoprotection of a sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprising an inorganic UV-filter by the addition of a certain mycosporine-like amino acid compound.
- the present invention relates to a method for providing anti-aging benefits to skin, whitening or preventing darkening of skin, improving the appearance of skin, diminishing the visible signs of skin aging and improving skin’s radiance and firmness by topically applying the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention to the skin.
- Background Art [0002] The negative effects of exposure of UV light are well-known. Prolonged exposure to sunlight causes damage such as sunburn to the skin and dries out hair making it brittle.
- UVA long wave ultraviolet A
- UVB shortwave ultraviolet B
- UVA is 230145 further divided into two wavelength ranges namely UVA1 (340 to 400 nm) and UVA2 (320 to 340 nm).
- UVA rays account for the majority (95 %) of UV radiation.
- UVB and UVC rays have longer wavelength than UVB and UVC rays which means they have less energy (shorter wavelengths have more energy than longer wavelengths). Due to their longer wavelength, they can penetrate into the dermis which is predominantly made up of collagen.
- UVA rays When UVA rays are absorbed by the skin they create free radicals which can damage cells and DNA and break down collagen. This is why UVA rays are highly associated with premature aging.
- the skin damage caused by UVA radiation accelerates the appearance of aging, for example, loss of skin elasticity and the appearance of wrinkles. This process is commonly referred to as photo-aging. As skin ages, the outer skin layer (epidermis) thins, even though the number of the cells remain largely unchanged. The number of pigment-containing cells (melanocytes), however, decreases.
- UVA radiation can trigger phototoxic or photo allergic skin reactions.
- UVB rays account for less than 5 % of UV radiation and, due to their shorter wavelength, can only penetrate the epidermis.
- UVB rays are by far the most damaging of the three types of UV rays. However, they are entirely absorbed by the atmosphere due to their short wavelength and, thus, are unable to reach our skin. 230145 [0007] To attenuate these negative effects of UV-radiation, i.e.
- anti-sun/sunscreen compositions comprising screening agents that are active in the UVA range and in the UVB range, i.e. within the full range of 280 nm to 400 nm, are generally used.
- UV-filters are compounds which have a pronounced absorption capacity for ultraviolet radiation.
- UV-filters are classified as UVA and UVB filters depending on the location of their absorption maxima; if a UV-filter absorbs both UVA and UVB, it is referred to as a UVA/UVB broadband absorber or UVA/UVB broadband filter.
- UV-filters which can be used for the protection of skin are regulated in the USA by the America FDA via their OTC monograph system and are regulated in the European Union by the Cosmetic Regulation. Regulations covering the use of UV-filters exist in other countries and regions as well. These regulations not only stipulate the filters which can be used but also fix a maximum usage level for each UV-filter.
- sunscreen formulations typically comprise a combination of several organic UV-filters, which may be supplemented with inorganic UV-filters in order to increase the efficacy.
- organic UV-filters are subject to continuously increasing concerns because they are suspected to be a possible cause of skin irritations and allergies in sensitive person and their potentially harmful effect on the environment.
- some organic UV-filters suffer from photo-instability.
- inorganic UV-filters are photostable and give a broader spectrum protection covering UVA and UVB. It is also known that inorganic UV-filters cause less skin irritation.
- inorganic UV-filters are typically employed in the form of nanoscale pigments.
- the smaller size of these mineral particles increases their cosmetic acceptability by users as they are much less visible after application.
- nanoscale pigments are prone to be less effective in UV shielding.
- a sunscreen product of cosmetic or pharmaceutical preparation comprising an inorganic UV-filter.
- the present invention provides in a first aspect a sunscreen product or a cosmetic or pharmaceutical preparation, comprising or consisting of (a) at least one inorganic UV-filter; and 230145 (b) at least one mycosporine-like amino acid compound, represented either by the general formula (V) formula (V), as defined herein, or a tautomer or a stereoisomer or a salt thereof; or represented by the general formula (VI) “ formula (VI), as defined herein, or a tautomer or a stereoisomer or a salt thereof; or any mixture of the afore-mentioned compounds.
- a sunscreen product or a cosmetic or pharmaceutical preparation comprising or consisting of (a) at least one inorganic UV-filter; and 230145 (b) at least one mycosporine-like amino acid compound, represented either by the general formula (V) formula (V), as defined herein, or a tautomer or a stereoisomer or a salt thereof; or represented by the general formula (VI) “ formula
- the present invention provides for the use of at least one mycosporine-like amino acid compound (b) as defined herein or a mixture thereof for boosting the SPF performance and the UVA photoprotection of a sunscreen product, 230145 cosmetic or pharmaceutical preparation or homecare product comprising at least one inorganic UV-filter.
- the present invention relates to a method of enhancing or boosting the SPF performance and the UVA photoprotection of a sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprising at least one inorganic UV-filter, said method comprising the addition of an effective amount of a mycosporine-like amino acid compound (b) as defined herein or a mixture thereof to said sunscreen product, cosmetic or pharmaceutical preparation or homecare product.
- the present invention relates to a method of providing anti-aging benefits to skin, whitening or preventing darkening of skin, improving the appearance of skin, diminishing the visible signs of skin aging and improving skin’s radiance and firmness by topically applying the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention to the skin.
- compound(s) or “compound(s) of the present invention” refers to all compounds encompassed by the structural formulae (V) and/or formula (VI) and/or formula (VII) and/or formula (XIII) and/or formula (IX) and/or formula (X) and/or formula (A) and their sub-formulae disclosed herein and includes each subgenus and all specific compounds within the formula whose structure is disclosed herein.
- the compounds may be identified by either their chemical structure and/or chemical name. When the chemical structure and chemical name are in conflict, the chemical structure determines the identity of the compound.
- the term “at least one ...compound” means that the food or cosmetic or pharmaceutical preparation, in particular sunscreen product, or homecare product according to the present invention can comprise either one of said subsequently 230145 described individual compound or a mixture of two, three, four, five, six or even more different of said subsequently compounds.
- Cosmetic or pharmaceutical preparations in the context of the present invention are compositions for cosmetic or pharmaceutical purposes which contain a UV- filter in order to protect skin, hair or nails against UV-radiation.
- the cosmetic or pharmaceutical preparations according to the present invention are useful for providing anti-aging benefits to skin, whitening or preventing darkening of skin, improving appearance of skin, diminishing the visible signs of skin aging and improving skin’s radiance and firmness.
- sunscreen composition is to be understood as not only including sunscreen compositions, but also any cosmetic compositions that provide UV protection.
- the sunscreen composition may comprise one or more active agents, e.g., organic UV- filters, as well as other ingredients or additives, e.g., emulsifiers, emollients, viscosity regulators, stabilizers, preservatives, or fragrances.
- Sunscreens come as lotions, sprays, gels, foams (such as an expanded foam lotion or whipped lotion), sticks, powders and other topical products.
- UV-absorbing compounds are used not only in sunscreen, but also in other personal care products, such as lipstick, shampoo, hair spray, body wash, toilet soap, and insect repellent.
- homecare products in the context of the present invention are the essentials for daily care and cleaning purpose in households.
- the home care products generally include laundry detergents (powder, liquid and tablet), fabric conditioners, dishwashing detergents (liquid and tablet), hard floor and surface cleaners, glass cleaners, carpet cleaners, oven cleaners, air fresheners, disinfectants, stain removers, car wash products. These products are usually manufactured in the form of a liquid, powder, spray, granules 230145 and others.
- sunscreen containing formulations prevent premature photodamage and photobleaching to surfaces and the homecare formulation itself.
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product of the present invention provide an enhanced SPF performance and UVA photoprotection, as well as broad-spectrum photo-protection from UV radiation.
- UV-filters are compounds suitable for protecting body-care and household cleaning and treating agents against photolytic degradation.
- photostability refers to the ability of a UV-filter or any other molecule, which is exposed to sunlight, to stay stable upon irradiation. In particular, this means that the compound does not undergo a degradation process upon UV radiation.
- Sun Protection Factor indicates a sunscreen’s, cosmetic or pharmaceutical preparation’s or homecare product’s ability to protect against UVB rays but does not adequately designate to what extent (if any) a sunscreen composition protects against UVA radiation.
- SPF is a measure of how much solar energy (UV radiation) is required to produce sunburn on protected skin, i.e., in the presence of sunscreen, relative to the amount of solar energy required to produce sunburn on unprotected skin.
- An artificial UV source is used to irradiate skin until there is erythema (minimal erythema dose – MED) with and without sunscreen.
- SPF is then calculated by dividing the MED of the protected skin by the MED of the unprotected skin, i.e. how long it takes the skin to burn with and without sunscreen. In theory, this means that a sunscreen with an SPF of 50 means that you can be exposed to UV radiation for 50x longer before burning.
- UVA-photoprotection is expressed in UVA protection factor (UVA-PF).
- UVA-PF is similar to SPF in that it is a measure of how well a sunscreen protects the skin from UVA radiation. It is performed in a similar manner by irradiating the skin with UVA. This can be done in vivo with human skin or in vitro, where it is performed by applying the sunscreen to an acrylic or plastic slide and measuring how much UVA passes through 230145 the slide with or without the sunscreen.
- the PPD Persistent Pigment Darkening
- the UVAPPDPF of the sunscreen product, cosmetic or pharmaceutical preparation or homecare product is typically at least 4.
- Skin properly treated with a cosmetic composition having a UVAPPDPF of 4 means that it takes about 4 time longer for the skin to darken (i.e. to reach the threshold level of pigment darkening) compared to skin without treatment with the sunscreen product, cosmetic or pharmaceutical preparation or homecare product.
- the term “broad-spectrum photo-protection” means photo-protection from both UVA and UVB radiation. Broad-spectrum is based on the breadth of protection offered by a sunscreen in the UVA and UVB spectrum. In order for a sunscreen to be considered broad-spectrum, it must have achieved a critical wavelength of at least 370 nm. A critical wavelength > 370 nm is a rigorous minimum that sunscreen products should achieve to be labelled as broad-spectrum”.
- critical wavelength is defined as the wavelength at which the area under the UV protection curve (% protection versus wavelength) represents 90 % of the 230145 total area under the curve in the UV region (280 - 400 nm).
- a critical wavelength of 370 nm indicates that the protection of the sunscreen composition is not limited to the wavelengths of UV-B, i.e. wavelengths from 280 - 320 nm, but extends to 370 nm in such a way that 90 % of the total area under the protective curve in the UV region are reached at 370 nm.
- the higher the critical wavelength the better the protection against UV radiation.
- the critical wavelength ( ⁇ c)
- mathematical integration of the measured spectral absorbance from 290 nm to 400 nm is performed to calculate the area beneath the absorbance curve.
- the critical wavelength value is based upon the inherent shape and breadth of the absorbance curve, not its amplitude.
- the critical wavelength is the wavelength below which 90 % of the area under the absorbance curve sides.
- the critical wavelength for a UVB sunscreen is less than that for a sunscreen that protects against both UVB and UVA.
- a higher critical wavelength ensures more UV protection, especially from longer wavelength UVA rays.
- a sunscreen with a critical wavelength of 370 nm provides more protection against UVA rays than a sunscreen with a critical wavelength of 350 nm.
- the primary object of the present invention is solved by a sunscreen product, cosmetic, especially dermatological, or pharmaceutical preparation or homecare product comprising or consisting of (a) at least one inorganic UV-filter; and (b) at least one mycosporine-like amino acid compound, represented either by the general formula (V) 230145 formula (V), wherein - Z is selected from the group consisting of O-R2’ or amide’; - R1’ is selected from the group consisting of CH2, unsubstituted or substituted CH(alkyl), unsubstituted or substituted C(alkyl)2, unsubstituted or substituted CH(cycloalkyl), unsubstituted or substituted CH(aryl), unsubstituted or substituted CH(heterocycloalkyl), unsubstituted or substituted CH(he
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the invention comprises at least one inorganic UV-filter (a) that provide protection from UVA and/or UVB radiation.
- a UV-filter is a compound or a mixture of compounds that block or absorb ultraviolet (UV) light. UV classifications include UVA (320 to 400 nm), UVB (290 to 320 nm) and UVC (200 to 280 nm). UV-absorbing compounds are used not only in sunscreen, but also in other personal care products, such as lipstick, shampoo, hair spray, body wash, toilet soap, and insect repellent. Chemical filters protect against UV- radiation by absorbing, reflecting, or scattering.
- UV-filters such as titanium dioxide (TiO2) and zinc oxide (ZnO).
- UVB Absorption, mainly of UVB, is done by organic UV-filters, which are known as chemical UV-filters.
- the sunscreen product or cosmetic or pharmaceutical preparations according to the present invention provide broad spectrum photo protection, i.e. protection from both UVA and UVB.
- the at least one inorganic UV-filter (a) is selected from the group of pigments consisting of titanium dioxide (TiO2) (amorphous or crystallized in rutile and/or anatase form), zinc oxide (ZnO), iron oxide (Fe2O3), zirconium oxide (ZrO2), silicon dioxide (SiO2), manganese oxide (e.g. MnO), aluminium oxide (Al2O3), cerium oxide (Ce2O3), barium carbonate (BaCO3), calcium carbonate (CaCO3), and mixtures thereof.
- the at least one inorganic UV-filter is titanium dioxide, zinc oxide, and mixtures thereof, more preferably the at least one inorganic UV-filter is titanium oxide and/or zinc oxide, and most preferably, the at least one inorganic UV-filter is zinc oxide.
- ZnO has a broad UVA/UVB absorption curve, while TiO2 provides better UVB protection.
- the at least one inorganic UV-filter is in form of particles having a weight medium particle size d50 from 1 nm to 1000 nm, preferably from 3 nm to 800 nm, more preferably from 5 nm to 600 nm, and most preferably from 10 nm to 400 nm.
- the inorganic UV-filters also encompass nano pigments (mean size of the primary particles: generally from 1 nm to 100 nm, preferably from 3 nm to 90 nm, more preferred from 5 nm to 80 nm and most preferred from 10 to 70 nm) of untreated or treated metal oxides such as, for example, nano pigments of titanium dioxide (TiO2) (amorphous or crystallized in rutile and/or anatase form), zinc oxide (ZnO), iron oxide (Fe2O3), zirconium oxide (ZrO2), silicon dioxide (SiO2), manganese oxide (e.g.
- nano pigments mean size of the primary particles: generally from 1 nm to 100 nm, preferably from 3 nm to 90 nm, more preferred from 5 nm to 80 nm and most preferred from 10 to 70 nm
- untreated or treated metal oxides such as, for example, nano pigments of titanium dioxide (TiO2) (amorphous or crystallized
- the treated nano pigments and non-nano pigments are pigments that have undergone one or more surface treatments of chemical, electronic, mechanochemical and/or mechanical nature with compounds, such as amino acids, beeswax, fatty acids, fatty acid esters, fatty alcohols, anionic surfactants, lecithins, sodium, potassium, zinc, iron or aluminium salts of fatty acids, metal (titanium or aluminium) alkoxides, polyethylene, silicones, proteins (collagen or elastin), alkanolamines, silicon oxides, metal oxides, sodium hexametaphosphate, alumina or glycerol, hydrated silica, stearic acid, jojoba esters, or glutamic acid derivates.
- compounds such as amino acids, beeswax, fatty acids, fatty acid esters, fatty alcohols, anionic surfactants, lecithins, sodium, potassium, zinc, iron or aluminium salts of fatty acids, metal (
- the treated nano pigments and non-nano pigments may more particularly be titanium oxides treated with silica and alumina, alumina and aluminium stearate, alumina and aluminium laurate, aluminium hydroxide, iron oxides and iron stearate, silica, alumina and silicone, sodium hexametaphosphate, octyltrimethoxysilane, alumina and stearic acid, alumina and glycerol, or alumina and silicone or polyhydroxy stearic acid, hydrated silica, jojoba esters, steaoryl glutamic acid, glutamic acid and derivates, trimethoxycaprylylsilane, glycerin, dimethicone, hydrogen dimethicone, simethicone or combinations thereof.
- titanium oxide nano pigments treated with a silicone are preferably TiO2 treated with octyltrimethylsilane, preferably for which the mean size of the 230145 elementary particles is from 25 to 40 nm; TiO2 treated with a polydimethylsiloxane, preferably for which the mean size of the elementary particles is 21 nm; or TiO2 treated with a polydimethylhydrogenosiloxane, preferably for which the mean size of the elementary particles is 25 nm.
- the coated zinc oxide nano pigments and zinc oxide non-nano pigments are for example ZnO coated with polymethylhydrogenosiloxane; ZnO dispersions in cyclopolymethylsiloxane/ oxyethylenated polydimethylsiloxane, containing 30 % or 80 % of nano or non-nano zinc oxides coated with silica and polymethylhydrogenosiloxane; ZnO coated with perfluoroalkyl phosphate and copolymer based on perfluoroalkylethyl as a dispersion in cyclopentasiloxane; ZnO coated with dimethoxydiphenylsilanetriethoxycaprylylsilane cross-polymer; ZnO coated with glutamic acid; ZnO coated with octyltriethoxy silane; ZnO coated with dimethicone; ZnO coated with silicone-grafted acrylic polymer, dispersed in
- particulate UV-filters or inorganic pigments which can optionally be hydrophobed, such as the oxides of iron (Fe2O3), zirconium (ZrO2), silicon (SiO2), manganese oxide (e.g. MnO), aluminium oxide (Al2O3), cerium (e.g. Ce2O3), barium carbonate (BaCO3), calcium carbonate (CaCO3), or mixtures thereof.
- the afore specified inorganic UV-filters are used in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product either as a single component or in a mixture with two, three, four or more further of said inorganic UV-filters.
- the component (b) in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the first aspect of the present invention is at least one mycosporine-like amino acid compound represented either by the general formula (V) formula (V), as defined herein; or represented by the general formula (VI) “ formula (VI), as defined herein.
- Mycosporine-like amino acids are small secondary metabolites produced by organisms that live in environments with high volumes of sunlight, usually marine environments.
- the MAAs are imine derivatives of mycosporines and contain an amino-cyclohexene-imine ring linked to an amino acid, amino alcohol or amino group.
- the compounds are capable of electron delocalization.
- said compounds demonstrate antioxidant qualities.
- halogen residue/moiety or group alone or as part of another substituent according to the present invention refers to F, Cl, Br or I.
- alkyl alone or as part of another substituent according to the present invention refers to a saturated or mono- or polyunsaturated linear or branched monovalent hydrocarbon radical obtained by removing a hydrogen atom from a single carbon atom of a corresponding parent alkane.
- alkyl also includes any alkyl moieties in radicals derived therefrom, such as alkoxy, alkylthio, alkylsulphonyl saturated linear or branched hydrocarbon radicals having 1 to 10, 1 to 8, 1 to 6, or 1 to 4 carbon atoms.
- alkyl radical is further bonded to another atom, it becomes an alkylene radical or alkylene group.
- alkylene also refers to a divalent linear or branched alkyl. For example, -CH2CH3 is an ethyl, while -CH2CH2- is an ethylene.
- alkylene alone or as part of another substituent refers to a saturated linear or branched divalent hydrocarbon radical obtained by removing two hydrogen atoms from a single carbon atom or two different carbon atoms of a starting alkane.
- the linear or branched alkyl group or alkylene group comprises 1 to 10 carbon atoms.
- the linear or branched alkyl group or alkylene group comprises 1 to 6 carbon atoms.
- More preferred according to the invention are saturated linear or branched C1 to C6 alkyl groups or saturated linear or branched C1 to C6 alkylene groups.
- alkyl radicals/moieties or alkyl groups include, but are not limited to: C1 to C6 alkyl comprising methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2- methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2- dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1- methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2- dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl,
- the alkyl radical/moiety is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, more preferred from the group consisting of methyl and ethyl.
- the alkyl group or alkylene group as defined above may further be substituted.
- alkyl or “alkylene” further includes radicals or groups having any degree of saturation, i.e., groups having only single carbon-carbon bonds (“alkyl” or “alkylene"), groups having one or more double carbon-carbon bonds (“alkenyl”), radicals having one or more triple carbon-carbon bonds (“alkynyl”), and groups having a mixture of single, double and/or triple carbon-carbon bonds.
- alkenyl also includes the corresponding cis/trans isomers. 230145
- the linear or branched alkenyl group comprises 2 to 10 carbon atoms. In other preferred variants, the linear or branched alkenyl group comprises 2 to 6 carbon atoms. [0080] In still further preferred variants, the linear or branched alkenyl group comprises 2 to 4 carbon atoms. [0081] Preferred according to the invention are mono- or di-unsaturated linear or branched C1 to C6 alkenyl groups.
- Typical alkenyl radicals or alkenyl groups include, but are not limited to, ethenyl; propenyls such as prop-1-en-1-yl, prop-1-en-2-yl, prop-2-en-1-yl (allyl), prop-2-en-2-yl, cycloprop-1-en-1-yl, cycloprop-2-en-1-yl; butenyls such as but-1-en-1-yl, but-1-en-2-yl, 2- methyl-prop-1-en-1-yl, but-2-en-1-yl, but-2-en-2-yl, buta-1,3-dien-1-yl, buta-1,3-dien-2-yl and the like.
- alkenyl group as defined above may further be substituted.
- alkynyl alone or as part of another substituent according to the present invention refers to an unsaturated linear or branched monovalent hydrocarbon radical having at least one carbon-carbon triple bond (C ⁇ C triple bond).
- the linear or branched alkynyl group comprises 2 to 10 carbon atoms. In other preferred variants, the alkynyl group comprises 2 to 6 carbon atoms. In still further preferred variants, the alkynyl group comprises 2 to 4 carbon atoms.
- alkynyl radicals/moieties or alkynyl groups include, but are not limited to, ethynyl; propynyls such as prop-1-yn-1-yl, prop-2-in-1-yl, etc.; butynyls such as but-1-in- 1-yl, but-1-in-3-yl, but-3-in-1-yl, and the like.
- the alkynyl group as defined above may further be substituted.
- the alkyl group or alkylene group as defined above may further be substituted.
- alkoxy alone or as part of another substituent according to the present invention refers to a linear or branched radical of the formula -O-R, where R is alkyl or substituted alkyl, as defined herein.
- the linear or branched alkoxy group comprises 2 to 10 carbon atoms.
- the linear or branched alkoxy group comprises 2 to 6 carbon atoms.
- the linear or branched alkoxy group comprises 2 to 4 carbon atoms.
- Most preferred according to the invention are linear or branched C1 to C6 alkoxy groups.
- Typical alkoxy radicals/moieties or alkoxy groups include C1 to C6 alkoxy comprising C1 to C4 alkoxy such as. methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy; as well as pentoxy, 1- methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2- dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2- methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2- dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3- dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2- trimethylpropoxy, 1-ethyl
- the alkoxy radical or alkoxy group is selected from the group consisting of methoxy (-O-methyl), ethoxy (-O-ethyl), propoxy (-O-propyl) and 230145 butoxy (-O-butyl), more preferred from the group consisting of methoxy (-O-methyl) and ethoxy (-O-ethyl).
- the alkoxy group or alkylene group as defined above may further be substituted.
- alkylthio or “thioalkoxy” alone or as part of another substituent according to the present invention refers to a radical of the formula -S-R, wherein R is alkyl or substituted alkyl, as defined herein.
- alkyl or “alkylene” also includes heteroalkyl radicals or heteroalkyl groups.
- heteroalkyl by itself or as part of other substituents refers to alkyl groups in which one or more of the carbon atom(s) is/are independently replaced by the same or another heteroatom or by the same or another heteroatomic group(s).
- Typical heteroatoms or heteroatomic groups that may replace the carbon atoms include, but are not limited to, -O-, -S-, -N-, -Si-, -NH-, -S(O)- , -S(O)2-, -S(O)NH-, -S(O)2NH-, and the like, and combinations thereof.
- the heteroatoms or heteroatomic groups may be located at any internal position of the alkyl group.
- alkyl group or alkylene group as defined above may further be substituted.
- cycloalkyl alone or as part of another substituent according to the present invention refers to a saturated or mono- or polyunsaturated, non-aromatic, cyclic monovalent hydrocarbon radical in which the carbon atoms are ring-linked and which has no heteroatom.
- the carbon ring can occur as a monocyclic compound, which has only a single ring, or as a polycyclic compound, which has two or more rings.
- the term "cycloalkyl" includes a three- to ten- membered monocyclic cycloalkyl radical or cycloalkyl group or a nine- to twelve- membered polycyclic cycloalkyl radical or cycloalkyl group.
- the cycloalkyl moiety comprises a five-, six- or seven-membered monocyclic cycloalkyl moiety or a nine- to twelve-membered bicyclic cycloalkyl moiety.
- a cycloalkyl radical or group comprises 3 to 20 carbon atoms. In an even more preferred embodiment, a cycloalkyl radical comprises 6 to 15 carbon atoms. In a most preferred embodiment, a cycloalkyl radical comprises 6 to 10 carbon atoms. Most preferred are monocyclic C3 to C7 cycloalkyl groups.
- Typical cycloalkyl radicals or cycloalkyl groups include, but are not limited to, saturated carbocyclic radicals having 3 to 20 carbon atoms, such as C3 to C12 carbocyclyl, comprising cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, and cyclododecyl; cyclopentyl, 230145 cyclohexyl, cycloheptyl, as well as cyclopropyl-methyl, cyclopropyl-ethyl, cyclobutyl- methyl, cyclobutyl-ethyl, cyclopentyl-methyl, cyclopentyl-ethyl, cyclohexyl-methyl, or C3- to C7-carb
- cycloalkyl radicals or cycloalkyl groups preferred according to the invention include but are not limited to naphthyl, indenyl, groups and the like.
- cycloalkenyls are compounds with one, two or more double bond(s), where the number of possible, mostly conjugated double bonds in the molecule depends on the ring size.
- Typical cycloalkenyls include, but are not limited to, cyclopropenyl, cyclopentenyl, cyclohexenyl, cyclopentadienyl, and the like.
- cycloalkyl further includes cycloalkynyls, i.e. unsaturated, -C ⁇ C-triple bonds, containing cyclic hydrocarbon radicals between two carbon atoms of the ring molecule, the triple bond depending on the ring size for reasons of ring tension.
- Typical cycloalkynyles include cyclooctin.
- aryl alone or as part of another substituent according to the present invention refers to a monovalent aromatic hydrocarbon radical derived by removing a hydrogen atom from a single carbon atom of an aromatic ring SY-stem.
- aryl includes a three- to ten-membered monocyclic aryl radical or aryl group or a nine- to twelve-membered polycyclic aryl radical or aryl group.
- the carboaryl radical comprises a five- , six- or seven-membered monocyclic carboaryl radical or a nine- to twelve-membered bicyclic carboaryl radical.
- the aryl radical comprises 3 to 20 carbon atoms.
- the aryl moiety comprises 6 to 15 ring atoms.
- an aryl radical comprises 6 to 10 carbon atoms.
- Most preferred according to the invention are monocyclic C3 to C10 aryl groups. Most preferred are monocyclic C3 to C7 aryl groups.
- Typical aryl radicals include, without being limited thereto, benzene, phenyl, biphenyl, naphthyl such as 1- or 2-naphthyl, tetrahydronaphthyl, fluorenyl, indenyl, and phenanthrenyl.
- Typical carboaryl moieties further include, but are not limited to, groups derived from aceanthrylene, acenaphthylene, acephenanthrylene, anthracene, azulene, benzene, chrysene, corone, fluoranthene, fluorene, hexacene, hexaphene, hexalene, as- indacene, S-indacene, indane, indene, naphthalene, octacene, octaphene, octalene, ovalene, penta-2,4-diene, pentacene, pentalene, pentaphene, perylene, phenalene, phenanthrene, picene, pleiadene, pyrene, pyranthrene, rubicene, triphenylene, trinaphthalene and the like.
- Aromatic polycyclic aryl radicals or aryl groups preferred according to the invention include, but are not limited to, naphthalene, biphenyl and the like.
- the aryl moiety or group, as defined above, may further be substituted.
- arylalkyl alone or as part of another substituent according to the present invention refers to an acyclic alkyl group in which one of the hydrogen atoms attached to a carbon atom, typically a terminal or sp carbon atom, is replaced by an aryl group as defined herein. In other words, arylalkyl may also be considered as alkyl substituted by aryl.
- Typical arylalkyl groups include, but are not limited to, benzyl, 2- phenylethan-1-yl, 2-phenylethen-1-yl, naphthylmethyl, 2-naphthylethan-1-yl, 2- naphthylethen-1-yl, naphthobenzyl, 2-naphthophenylethan-1-yl, and the like.
- heteroarylalkyl alone or as part of another substituent refers to a cyclic alkyl group in which one of the hydrogen atoms attached to a carbon atom is replaced by a heteroaryl group.
- the heteroarylalkyl group is a 6- to 20-membered heteroarylalkyl, e.g., the alkyl, alkenyl, or alkynyl group of the heteroarylalkyl is a C1- to C6-alkyl and the heteroaryl group is a 5- to 15-membered heteroaryl group.
- the heteroarylalkyl is a 6- to 13-membered heteroarylalkyl, e.g., the alkyl, alkenyl, or alkynyl group is a C1- to C3-alkyl and the heteroaryl group is a 5- to 10-membered heteroaryl.
- heterocycloalkyl alone or as part of another substituent according to the present invention refers to a saturated or mono- or polyunsaturated, non-aromatic, cyclic monovalent hydrocarbon radical in which one or more carbon atom(s) is/are independently replaced by the same or a different heteroatom.
- Typical heteroatoms to replace the carbon atom(s) include, but are not limited to, N, P, O, S, Si, etc.
- heterocycloalkyl groups include, without being limited thereto, groups derived from epoxides, azirines, thiiranes, imidazolidine, morpholine, piperazine, piperidine, pyrazolidine, pyrrolidone, quinuclidine and the like.
- the heterocycloalkyl moiety or group comprises 3 to 20 ring atoms.
- the heterocycloalkyl moiety comprises 6 to 15 ring atoms.
- the heterocycloalkyl moiety comprises 6 to 10 carbon atoms.
- heterocycloalkyl can occur as a monocyclic compound, which has only a single ring, or as a polycyclic compound, which has two or more rings, such as bicyclic, tricyclic or spirocyclic.
- heterocycloalkyl includes three- to seven-membered, saturated or mono- or polyunsaturated heterocycloalkyl moieties comprising one, two, three or four heteroatoms selected from the group consisting of O, N and S.
- the heteroatom or heteroatoms may occupy any position in the heterocycloalkyl ring.
- heterocycloalkyl includes a three- to ten- membered monocyclic heterocycloalkyl radical or a nine- to twelve-membered polycyclic heterocycloalkyl radical.
- the heterocycloalkyl moiety comprises a five-, six- or seven-membered monocyclic heterocycloalkyl moiety or a nine- to twelve-membered bicyclic heterocycloalkyl moiety.
- Most preferred according to the invention are monocyclic heterocycloalkyl radicals comprising 3 to 12 carbon atoms. Most preferred are monocyclic heterocycloalkyl radicals having 5 to 7 ring atoms.
- Typical heterocycloalkyl moieties include, but are not limited to: Five- or six- membered, saturated or monounsaturated heterocycloalkyl containing one or two nitrogen atoms and/or one oxygen or sulphur atom or one or two oxygen and/or sulphur atoms as ring members comprising 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2- tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3- lsoxazolidinyl, 4-lsoxazolidinyl, 5-lsoxazolidinyl, 3-lsothiazolidinyl, 4-lsothiazolidinyl, 5- lsothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl,
- heterocycloalkyl moiety or group, as defined above, may further be substituted.
- heteroaryl by itself or as part of another substituent according to the present invention refers to a monovalent heteroaromatic radical obtained by removing a hydrogen atom from a single atom of a heteroaromatic ring system. Typical heteroaryl radicals, or.
- Heteroaryl groups include, but are not limited to, those derived from acridine, ⁇ -carboline, chroman, chromium, cinnoline, furan, imidazole, indazole, indole, indoline, indolizine, isobenzofuran, isochromium, isoindole, isoindoline, isoquinoline, isothiazole, isoxazole, naphthyridine, oxadiazole, oxazole, perimidine, phenanthridine, phenanthroline, phenazine, phthalazine, pteridine, purine, pyran, pyrazine, pyrazole, pyridazine, pyridine, pyrimidine, pyrrole, thiazole, thiophene, triazole, xanthene and the like are derived.
- heteroaryl moiety can occur as a monocyclic compound having only a single ring or as a polycyclic compound having two or more rings.
- heteroaryl includes a three- to ten- membered monocyclic heteroaryl radical or a nine- to twelve-membered polycyclic heteroaryl radical.
- the heteroaryl moiety comprises a five-, six- or seven-membered monocyclic heteroaryl moiety or a nine- to twelve- membered bicyclic heteroaryl moiety.
- heteroaryl includes three- to seven-membered monocyclic heteroaryl radicals comprising one, two, three or four heteroatoms selected from the group consisting of O, N and S.
- the heteroatom or heteroatoms may occupy any position in the heteroaryl ring.
- the heteroaryl moiety or group comprises 3 to 20 ring atoms.
- the 230145 heteroaryl moiety comprises 6 to 15 ring atoms.
- the heteroaryl group comprises 6 to 10 ring atoms.
- Most preferred according to the invention are monocyclic C3 to C7 heteroaryl groups.
- heteroaryl moieties or heteroaryl groups include, but are not limited to, those derived from furan, thiophene, pyrrole, benzothiophene, benzofuran, benzimidazole, indole, pyridine, pyrazole, quinoline, imidazole, oxazole, isoxazole, and pyrazine.
- Five-membered aromatic heteroaryl radicals containing, in addition to carbon atoms, one, two or three nitrogen atoms or one or two nitrogen atoms and one sulphur or oxygen atom as ring atoms include 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3- pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2- thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-lmidazolyl, 4-lmidazolyl, and 1,3,4-triazol-2-yl.
- Five-membered aromatic heteroaryl radicals containing one, two, three or four nitrogen atoms as ring atoms include 1-, 2- or 3-pyrrolyl, 1-, 3- or 4-pyrazolyl, 1-, 2- or 4- lmidazolyl, 1,2,3-[1H]-triazol-1-yl, 1,2,3-[2H]-triazol-2-yl, 1,2,3-[1H]-triazol-4-yl, 1,2,3- [1H]-triazol-5-yl, 1,2,3-[2H]-triazol-4-yl, 1,2,4-[1H]-triazol-1-yl, 1,2,4-[1H]-triazol-3-yl, 1,2,4-[1H]-triazol-5-yl, 1,2,4-[4H]-triazol-4-yl, 1,2,4-[4H]-triazol-3-yl, [1H]-tetrazol-1-yl, [1H]
- Five-membered aromatic heteroaryl radicals containing a heteroatom selected from oxygen or sulphur and optionally one, two or three nitrogen atoms as ring atoms include 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 3- or 4-lsoxazolyl, 3- or 4-isothiazolyl, 2-, 4- or 5-oxazolyl, 2-, 4- or 5-thiazolyl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4- thiadiazol-2-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and 1,3,4-oxadiazol-2-yl.
- C-spirocycles in the context of the present application means compounds that have at least two molecular rings with only one common atom.
- the simplest spiro compounds are bicyclic (having just two rings) or have a bicyclic portion as part of the larger ring SY-stem, in either case with the two rings connected through the defining single common atom.
- the one common atom connecting the participating rings distinguishes spiro compounds from other bicyclic structures: from isolated ring compounds like biphenyl that have no connecting atoms, from fused ring compounds like decalin having two rings linked by two adjacent atoms, and from bridged ring compounds like norbornane with two rings linked by two non-adjacent atoms.
- Spiro compounds may be fully carbocyclic (all carbon) or heterocyclic (having one or more non- carbon atom, such as N, O and S).
- the common atom that connects the two (or sometimes three) rings is called the spiro atom.
- the spiro atom is a carbon atom.
- the C-spirocycles compound means compounds that are fully carbocyclic (all carbon).
- substituted in the context of the present invention means that one or more hydrogen atoms of the indicated radical or group is/are independently replaced by the same or a different substituent(s). Additionally, the term “substituted” specifically provides for one or more, i.e., two, three, four, five, six or more, substitutions commonly used in the art. However, it is generally known that the substituents should be selected so that they do not adversely affect the useful properties of the compound or its function.
- Suitable substituents in the context of the present invention preferably include halogen, perfluoroalkyl groups, perfluoroalkoxy groups, alkyl groups, alkenyl groups, alkynyl groups, hydroxy groups, oxo groups, mercapto groups, alkylthio groups, alkoxy groups, aryl or heteroaryl groups, aryloxy groups or heteroaryloxy groups, arylalkyl or heteroarylalkyl groups, arylalkoxy or heteroarylalkoxy groups, amino groups, alkyl and 230145 dialkylamino groups, carbamoyl groups, alkylcarbonyl groups, carboxyl groups, alkoxycarbonyl groups, alkylaminocarbonyl groups, dialkylaminocarbonyl groups, arylcarbonyl groups, aryloxycarbonyl groups, alkylsulfonyl groups, arylsulfonyl groups, cycloalkyl groups, cyano groups,
- Substituents or substituent groups useful for substituting saturated carbon atoms in the indicated group or radical more preferably include, but are not limited to, halogen, hydroxyl, alkyl, alkenyl, alkynyl, alkoxyl, -NH2, amino (primary, secondary, or tertiary), nitro, thiol, thioether, imine, cyano, amido, phosphonato, phosphine, carboxyl, thiocarbonyl, sulfonyl, sulfonamide, ketone, aldehyde, ester, acetyl, acetoxy, carbamoyl, oxygen (O); haloalkyl (e.g., trifluoromethyl); aminoacyl and aminoalkyl, carbocyclic cycloalkyl, which may be monocyclic or fused or non-fused polycyclic (e.g., cyclopropyl, cyclobutyl
- pyrrolidinyl piperidinyl, piperazinyl, morpholinyl, or thiazinyl
- carbocyclic or heterocyclic monocyclic or fused or non-fused polycyclic aryl (e.g., phenyl, naphthyl, pyrrolyl, indolyl, furanyl, thiophenyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, quinolinyl, isoquinolinyl, acridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, benzimidazolyl, benzothiophenyl, or benzofuranyl), -CO2CH3, -CONH2, -OCH2CONH2; -SO2NH2, -OCHF2, -CF3,
- the substituents used to replace a particular radical or radical may in turn be further substituted, typically with one or more of the same or different radicals selected from the various groups indicated above and as defined in detail above.
- substituted combinations such as substituted arylalkyl
- either the aryl or the alkyl group may be substituted, or both the aryl and the alkyl group may be substituted with one or more substituents.
- Z in the general formula (V) is either -O-R2’ or amide’.
- R1’ in the general formula (V) is CH2.
- R1’ in the general formula (V) is C(alkyl)2.
- R1’ in the general formula (V) is O.
- R1’ in the general formula (V) is S.
- R1’ in the general formula (V) is SO.
- R1’ in the general formula (V) is SO2.
- R1’ in the general formula (V) is NH.
- R1’ in the general formula (V) is N(alkyl).
- R1’ in the general formula (V) is either CH2 or C(alkyl)2.
- R2’ in the general formula (V) is H.
- R2’ in the general formula (V) is methyl.
- R2’ in the general formula (V) is ethyl.
- R2’ in the general formula (V) is propyl.
- R2’ in the general formula (V) is isopropyl.
- R2’ in the general formula (V) is butyl.
- R2’ in the general formula (V) is isobutyl.
- R2’ in the general formula (V) is tert-butyl. 230145
- R2’ in the general formula (V) is .
- R2’ in the general formula (V) is .
- R2’ in the general formula (V) is (2- ethyl-hexyl).
- R2’ in the general formula (V) is phenyl.
- R2’ in the general formula (V) is either H or ethyl or isopropyl or 2-ethylhexyl or phenyl.
- amide’ in the general formula (V) is NH2.
- amide’ in the general formula (V) is NH(alkyl), wherein alkyl is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and tert-butyl.
- amide’ in the general formula (V) is N(alkyl)2, wherein alkyl is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and tert-butyl.
- amide’ in the general formula (V) is -N(O- alkyl)(alkyl) (Weinreb amide), wherein alkyl is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and tert-butyl.
- amide’ in the general formula (V) is -N(OH)(H) (hydroxamate). 230145 [0173] Most preferred the amide’ in the general formula (V) is NH2, N(methyl)2 or N(ethyl)2 or -N(O-alkyl)(alkyl) (Weinreb amide), wherein alkyl is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and tert-butyl, or -N(OH)(H) (hydroxamate). [0174] In a preferred variant, R3’ in the general formula (V) is H.
- R3’ in the general formula (V) is methyl.
- R3’ in the general formula (V) is ethyl.
- R3’ in the general formula (V) is -O-methyl.
- Most preferred the R3’ in the general formula (V) is either H or methyl or -O- methyl.
- the mycosporine-like amino acid compound (b) of the general formula (V) is either an acid compound or an ester compound represented by the general formula (VII) 230145 ⁇ formula (VII), wherein R1’, R2’, R3’, R4’, R5’ and R6’ have the same meaning as defined herein for the general formula (V).
- the mycosporine-like amino acid compound (b) of the general formula (V) is an acid compound represented by the general formula (VII-acid) formula (VII-acid), wherein R1’, R3’, R4’, R5’ and R6’ have the same meaning as defined herein for the general formula (V).
- the mycosporine-like amino acid compounds according to the general formula (VII-acid) are particularly photo-stable and temperature-stable compounds and show stability in pH solution or in different emulsion types and do not degrade.
- said mycosporine-like amino acid compounds as defined herein have a better pH stability in a broader pH-range compared to their respective ester compounds which hydrolize, and, thus, are not stable in alkaline solutions having a pH higher than 9. 230145 [0187]
- said mycosporine-like amino acid compounds have also a better solubility in water compared to their corresponding ester compounds. Due to their better solubility in water, said mycosporine-like amino acid compounds can be incorporated into the water-phase of formulation in higher concentrations, resulting in an improved SPF performance boosting effect and an improved UVA photoprotection in sunscreen products, cosmetic or pharmaceutical preparations or homecare products.
- the mycosporine-like amino acid compound (b) of the general formula (V) is an ester compound represented by the general formula (VII-ester) formula (VII-ester), wherein R1’, R3’, R4’, R5’ and R6’ have the same meaning as defined herein for the general formula (V).
- the alkyl residue in the general formula (VII-ester) is methyl or ethyl or propyl or isopropyl or butyl or isobutyl or tert-butyl. Most preferred the alkyl residue in the general formula (VII-ester) is methyl.
- ester compounds are particularly stable.
- the mycosporine-like amino acid compound (b) of the general formula (V) is an amide compound represented by the general formula (VIII) 230145 ' formula (VIII), wherein R1’, amide’, R3’, R4’, R5’ and R6’ have the same meaning as defined herein for the general formula (V).
- the mycosporine-like amino acid compound (b) of the general formula (V) is an amide compound represented by the general formula (VIII-amide) ⁇ formula (VIII-amide), wherein R1’, R3’, R4’, R5’ and R6’ have the same meaning as defined herein for the general formula (V) and R11’ and R12’ are independently from each other selected from the group consisting of H, OH and alkyl.
- R11’ and/or R12’ are H.
- R11’ alkyl and R12’ alkyl in the general formula (VIII-amide) are independently from each other selected from the group consisting of methyl, ethyl, propyl, ispropropyl, butyl, isobutyl and tert-butyl.
- R11’ and/or R12’ in the general formula (VIII-amide) are each H or each methyl.
- the mycosporine-like amino acid compound (b) of the general formula (V) is a Weinreb amide compound represented by the general formula (VIII-Weinreb amide) formula (VIII-Weinreb amide), wherein R1’, R3’, R4’, R5’ and R6’ have the same meaning as defined herein for general formula (V).
- the alkyl residue in the general formula (VIII-Weinreb amide) is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, more preferred the alkyl residue is methyl.
- the mycosporine-like amino acid compound (b) of the general formula (V) is a hydroxamate compound represented by the general formula (VIII-hydroxamate derivative) 230145 formula (VIII-hydroxamate derivative), wherein R1’, R3’, R4’, R5’ and R6’ have the same meaning as defined herein for the general formula (V).
- the mycosporine-like amino acid compound (b) of the general formula (V) is an alkylated hydroxamate compound represented by the general formula (VIII-alkylated hydroxamate derivative) R6 ⁇ formula (VIII-alkylated hydroxamate derivative), wherein R1’, R3’, R4’, R5’ and R6’ have the same meaning as defined herein for the general formula (V).
- the alkyl residue in the general formula (VIII-alkylated hydroxamate derivative) is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, more preferred the alkyl is methyl.
- the mycosporine-like amino acid compound (b) is represented by the general formula (A) formula (A), wherein R1’, R3’, R4’, R5’ and R6’ have the same meaning as defined herein for the general formula (V).
- the same preferred variants as defined herein for the mycosporine-like amino acid compounds according to the general formula (V) apply analogously for the mycosporine-like amino acid compounds according to the general formulae (VII) or (VIII) and their variants or general formula (A).
- R1’’ in the general formula (VI) is CH2.
- R1’’ in the general formula (VI) is C(alkyl)2.
- R1’’ in the general formula (VI) is O.
- R1’’ in the general formula (VI) is S.
- R1’’ in the general formula (VI) is SO.
- R1’’ in the general formula (VI) is SO2.
- R1’’ in the general formula (VI) is NH.
- R1’’ in the general formula (VI) is N(alkyl).
- Most preferred the R1’’ in the general formula (VI) is either CH2 or C(alkyl)2.
- R2’’ in the general formula (VI) is -CH2-OH.
- X in the general formula (VI) is CH2.
- X in the general formula (VI) is O.
- X in the general formula (VI) is S. [0219] In a further preferred variant, X in the general formula (VI) is SO. [0220] In a further preferred variant, X in the general formula (VI) is SO2. [0221] In a further preferred variant, X in the general formula (VI) is NH. [0222] In a still further preferred variant, X in the general formula (VI) is N(alkyl), wherein alkyl is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and tert-butyl.
- X in the general formula (VI) is either S, SO or SO2.
- Y in the general formula (VI) is H. 230145 [0225] In a further preferred variant, Y in the general formula (VI) is methyl. [0226] In a further preferred variant, Y in the general formula (VI) is ethyl. [0227] In a further preferred variant, Y in the general formula (VI) is propyl. [0228] In a further preferred variant, Y in the general formula (VI) is is isopropyl. [0229] In a further preferred variant, Y in the general formula (VI) is butyl.
- Y in the general formula (VI) is isobutyl. [0231] In a further preferred variant, Y in the general formula (VI) is tert-butyl. [0232] In a further preferred variant, Y in the general formula (VI) is . [0233] In a further preferred variant, Y in the general formula (VI) is . [0234] In a preferred variant, Y in the general formula (VI) is (2-ethyl- hexyl). [0235] In a still further preferred variant, Y in the general formula (VI) is phenyl.
- Y in the general formula (VI) is H or ethyl or isopropyl or 2- ethylhexyl or phenyl.
- amide’’ in the general formula (VI) is NH2. 230145
- amide’’ in the general formula (VI) is NH(alkyl), wherein alkyl is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and tert-butyl.
- amide’’ in the general formula (VI) is N(alkyl)2, wherein alkyl is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and tert-butyl.
- amide’’ in the general formula (VI) is -N(O- alkyl)(alkyl) (Weinreb amide), wherein alkyl is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and tert-butyl.
- amide’’ in the general formula (V) is -N(OH)(H) (hydroxamate).
- Most preferred the amide’’ in the general formula (V) is NH2, N(methyl)2 or N(ethyl)2 or -N(O-alkyl)(alkyl) (Weinreb amide), wherein alkyl is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and tert-butyl, or -N(OH)(H) (hydroxamate).
- the mycosporine-like amino acid compound (b) is an alcohol compound represented by the general formula (IX-alcohol) formula (IX-alcohol), 230145 wherein R1’’, X, R4’’, R5’’ and R6’’ have the same meaning as defined herein for the general formula (VI).
- the mycosporine-like amino acid compound (b) of the general formula (VI) is an acid compound represented by the general formula (IX-acid) formula (IX-acid), wherein R1’’, X, R4’’, R5’’ and R6’’ have the same meaning as defined herein for the general formula (VI).
- the mycosporine-like amino acid compound (b) of the general formula (VI) is an ester compound represented by the general formula (VII-ester) R 6 ⁇ ⁇ formula (IX-ester), wherein R1’’, X, R4’’, R5’’ and R6’’ have the same meaning as defined herein for the general formula (VI).
- the alkyl residue in the general formula (VII-ester) is methyl or ethyl or propyl or isobutyl or butyl or isobutyl or tert-butyl, more preferred the alkyl residue is methyl.
- the mycosporine-like amino acid compound (b) of the general formula (VI) is an amide compound represented by the general formula (X) ⁇ R 6 ⁇ ⁇ formula (X), wherein R1’’, amide’’, X, R4, R5’’ and R6’’ have the same meaning as defined herein for the general formula (VI).
- the mycosporine-like amino acid compound (b) of general formula (VI) is an amide compound represented by the general formula (X-amide), ⁇ ⁇ R6 ⁇ ⁇ formula (X-amide), 230145 wherein R1’’, X, R4’’, R5’’ and R6’’ have the same meaning as defined herein for the general formula (VI) and R11”and R12” are independently from each other selected from the group consisting of H, OH and alkyl.
- R11’’ and/or R12’’ are H.
- the R11” alkyl and R12” alkyl in the general formula (X-amide) is methyl or ethyl or propyl or isopropyl or butyl or isobutyl or tert-butyl.
- R11’’ and/or R12’’ in the general formula (X-amide) are each H or each methyl.
- the mycosporine-like amino acid compound (b) of the general formula (VI) is a Weinreb amide compound represented by the general formula (X-Weinreb amide) R6 ⁇ ⁇ formula (X-Weinreb amide), wherein R1’’, X, R4’’, R5’’ and R6’’ have the same meaning as defined herein for the general formula (VI).
- the alkyl residue in the general formula (X-Weinreb amide) is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl and tert-butyl, more preferred the alkyl residue is methyl.
- the mycosporine-like amino acid compound (b) of the general formula (VI) is a hydroxamate compound represented by the general formula (X-hydroxamate derivative) R6 ⁇ ⁇ formula (X-hydroxamate derivative), wherein R1’’, X, R4’’, R5’’ and R6’’ have the same meaning as defined above for general formula (VI).
- the mycosporine-like amino acid compound (b) of general formula (VI) is an alkylated hydroxamate compound represented by the general formula (VIII-alkylated hydroxamate derivative) R6 ⁇ ⁇ formula (X-alkylated hydroxamate derivative), wherein R1’’, X, R4’’, R5’’ and R6’’ have the same meaning as defined herein for general formula (VI).
- the alkyl residue in the general formula (X-alkylated hydroxamate derivative) is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and tert-butyl, more preferred the alkyl residue is methyl.
- X-alkylated hydroxamate derivative is selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and tert-butyl, more preferred the alkyl residue is methyl.
- variants of the general formulae (V) and (VI) as defined herein include formula (VII), formula (VIII), formula (IX) and formula (X) as defined herein.
- Variants of the general formulae (VII) and (VIII) as defined herein include sub-formula (VII-acid), sub-formula (VII-ester), sub-formula (VIII-amide), sub-formula (VIII-Weinreb amide), sub-formula (VIII-hydroxamate derivative) and sub-formula (VIII-alkylated hydroxamate derivative) as defined herein.
- Variants of the general formulae (IX) and (X ) as defined herein include formula (IX-acid), formula (IX-ester), formula (X-amide), formula (X-Weinreb amide), formula (X-hydroxamate derivative) and formula (X-alkylated hydroxamate derivative) as defined herein.
- the mycosporine-like amino acid compound is a compound according to general formulae (V), wherein - Z is -O-R2’ or amide’; and/or - R1’ is selected from the group consisting of CH2, C(alkyl)2, O, S, SO, SO2, NH and N(alkyl); and/or - R2’ is selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, , , (2-ethyl- hexyl) and phenyl; or - amide’ is selected from the group consisting of NH2, NH(alkyl), N(alkyl)2, -N(O- alkyl)(alkyl) (Weinreb amide) and -N(OH)(H) (hydroxamate
- the mycosporine-like amino acid compound is a compound according to general formulae (VII) or (VIII), wherein - R1’ is selected from the group consisting of CH2, C(alkyl)2, O, S, SO, SO2, NH and N(alkyl); and/or - R2’ is selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, , , , (2-ethyl- hexyl) and phenyl; or - amide’ is selected from the group consisting of NH2, NH(alkyl), N(alkyl)2, -N(O- alkyl)(alkyl) (Weinreb amide) and -N(OH)(H) (hydroxamate); and/or 230145 - R3’ is selected from the group consisting of NH2, NH(alkyl), N(alkyl
- the mycosporine-like amino acid compound is a compound according to general formulae (V), wherein - Z is -O-R2’ or amide’; and/or - R1’ is selected from the group consisting of CH2 and C(methyl)2; and/or 230145 - R2’ is selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, , , , (2-ethyl- hexyl) and phenyl; or - amide’ is selected from the group consisting of NH2, NH(alkyl), N(alkyl)2, -N(O- alkyl)(alkyl) (Weinreb amide) and -N(OH)(H) (hydroxamate); and/or - R3’ is selected from the group consisting of
- the mycosporine-like amino acid compound is a compound according to general formulae (VII) or (VIII), wherein - R1’ is selected from the group consisting of CH2 and C(methyl)2; and/or - R2’ is selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, , , , (2-ethyl- hexyl) and phenyl; or - amide’ is selected from the group consisting of NH2, NH(alkyl), N(alkyl)2, -N(O- alkyl)(alkyl) (Weinreb amide) and -N(OH)(H) (hydroxamate); and/or - R3’ is selected from the group consisting of H, methyl, ethyl, -O-methyl,
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprises at least one mycosporine-like amino acid compound selected from the group consisting of the following compounds I-1 to I-128 according to the general formula (V) and II-1 to II-192 according to the general formula (VI): Table 1: 230145 230145 230145 230145 230145 230145 230145 230145 230145 or a tautomer or a stereoisomer or a salt of the afore-mentioned compounds, or any mixture of the afore-mentioned compounds.
- the phenyl ring may be unsubstituted or substituted.
- the substituents R4’, R5’, R6’, R4’’, R5’’, R6’’, amide’, Y, amide’’ and alkyl have the same meaning as defined for the mycosporine-like amino acid compounds according to general formula (V) or (VI) before.
- mycosporine-like amino acid compounds wherein in the general formula (V) R1’ is CH2 or C(methyl)2 or wherein in the general formula (VI) R1’’ is CH2 or C(methyl)2: Table 2: 230145 230145 ’ ’ ’ ’ ’ ’ ’ ’ ’ ’ ’ ’ ’ ’ ’ ’ ’ ’ ’ ’ ’ ’ ’ ’ ’ or a tautomer or a stereoisomer or a salt of the afore-mentioned compounds, or any mixture of the afore-mentioned compounds.
- the phenyl ring may be unsubstituted or substituted.
- - R2’ is selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, ethylhexyl) and phenyl;
- - amide’ is selected from the group consisting of NH2, NH(alkyl), N(alkyl)2, -N(O- alkyl)(alkyl) (Weinreb amide) and -N(OH)(H) (hydroxamate);
- - Y is selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, ethylhexyl) and phenyl;
- - amide’’ is selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, butyl, isobuty
- the mycosporine-like amino acid compound is a compound according to general formula (V) and its variants or formula (VI) and its variants, wherein R1’ or R1’’ are CH2.
- Such mycosporine-like amino acid compounds have a particular good water solubility.
- the mycosporine-like amino acid compound is a compound according to 230145 general formulae (VI), (IX), (X) and their variants, wherein X is selected from the group consisting of S, SO, and SO2.
- the mycosporine-like amino acid compound alters the UV absorption profile of the sunscreen product or cosmetic or pharmaceutical preparation and broaden the UV absorption spectrum of the formulation across the UV radiation spectrum.
- the mycosporine-like amino acid compound is a compound according to general formulae (VI), (IX, (X) and their variants, wherein X is S.
- the S atom in said compounds is prone to oxidation.
- the mycosporine-like amino acid compound is a compound according to general formulae (VI), (IX), (X) and their variants, wherein X is either SO or SO2.
- the mycosporine-like amino acid compound is a compound according to general formula (V), wherein - Z is -O-R2’ or amide’; and/or - R1’ is either CH2 or C(methyl)2; and/or - R2’ is either H or ethyl or isopropyl or 2-ethylhexyl or phenyl; or - amide’ is either NH2 or N(methyl)2 or N(ethyl)2 or -N(O-alkyl)(alkyl) (Weinreb amide) or -N(OH)(H) (hydroxamate); and/or - R3’ is either H
- the phenyl ring in the mycosporine-like amino acid compounds according to the general formulae (V) to (X) and their variants can be unsubstituted or substituted.
- the phenyl ring in the mycosporine-like amino acid compounds according to the general formulae (V) to (X) is unsubstituted, i.e. the substituents R4’, R5’ and R6’ on the phenyl ring in the general formula (V) is H; or the substituents R4’’, R5’’ and R6’’ on the phenyl ring in the general formula (VI) is H.
- the phenyl ring in the mycosporine-like amino acid compounds according to the general formulae (V) to (X) and their variants is substituted.
- the phenyl ring in the mycosporine-like amino acid compounds according to the general formula (V), (VII), (VIII) and their variants is unsubstituted, i.e. the substituents R4’, R5’ and R6’ are each H.
- the phenyl ring in the mycosporine-like amino acid compounds according to the general formula (VI), (IX), (X) and their variants is unsubstituted, i.e.
- the substituents R4’’, R5’’ and R6’’ are each H. Said compounds have an improved water solubility.
- the phenyl ring in the mycosporine-like amino acid compounds according to the general formulae (V) to (X) and their variants is monosubstituted, disubstituted or trisubstituted.
- the substituents R4’, R5’ and R6’ which may be identical or different, are independently from each other selected from the group consisting of H, OH, alkyl, preferably methyl, ethyl, propyl, iso-propyl, butyl, isobutyl or tert.-butyl, alkoxy,
- substituents R4’’, R5’’ and R6’’ which may be identical or different, are independently from each other selected from the group consisting of H, OH, alkyl, preferably methyl, ethyl, propyl, iso- propyl, butyl, isobutyl, tert-butyl, al
- the substituted phenyl ring bonded to the imino functionality is preferably selected from the group consisting of , 230145 ; wherein the dotted line designates the binding site to the cyclohexene imine ring.
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprises at least one mycosporine-like amino acid compound selected from the group consisting of: 230145 Table 3: - - - 230145 - - 230145 - - 230145 - - 230145 230145 230145 n or a tautomer or a stereoisomer or a salt of the afore-mentioned compounds, or any mixture of the afore-mentioned compounds.
- the compounds MAA-1 and MAA-13 are particularly preferred, since they have a pronounced SPF performance and UVA photoprotection improving effect.
- Most preferred are the acid compounds MAA-20, MAA-21, MAA-22, MAA-23, MAA-24, MAA-24, MAA-26, MAA-27, MAA-28, MAA-29, MAA-30, MAA-31, and the amide compounds MAA-32, MAA-33, MAA- 34, MAA-35, MAA-36, MAA-37, MAA-38, and MAA-39.
- Said compounds having an acid functionality or an amide functionality are photo-stable and temperature-stable and show stability in pH solution or in oil-in-water emulsions and does not degrade compared to the 230145 respective ester analogues.
- Particularly preferred are the acid compounds MAA-20, MAA-21, MAA-22, MAA-23, MAA-24, MAA-24, MAA-26, MAA-27, MAA-28, MAA-29, MAA-30 and MAA-31 due to their stability and their improved solubility in water.
- the mycosporine-like amino acid compounds MAA-20, MAA-21, MAA- 22, MAA-23, MAA-24, MAA-24, MAA-26, MAA-27, MAA-28, MAA-29, MAA-30 and MAA- 31 have a better stability in a broader pH-range compared to their respective ester compounds which hydrolize, and, thus, are not stable in alkaline solutions/formulations having a pH higher than 9.
- mycosporine-like amino acid compounds can be incorporated into the water-phase of emulsions in higher concentrations, resulting in an improved SPF performance boosting effect and an improved UVA photoprotection in sunscreen products, cosmetic or pharmaceutical preparations or homecare products.
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprises at least one mycosporine-like amino acid compound selected from the group consisting of: MAA-A: , MAA-B: 230145 , or a tautomer or a stereoisomer or a salt thereof, or any mixture of the afore-mentioned compounds, wherein alkyl is preferably either methyl or ethyl or propyl or isopropyl or butyl or isobutyl or tert-butyl, most preferred methyl.
- the mycosporine-like amino acid compounds according to the present invention and defined herein are used either as single substance or in a mixture with one, two or more different mycosporine-like amino acid compounds as defined herein.
- Particular preferred are mixtures of two mycosporine-like amino acid compounds according to the present invention and defined herein. Such mixtures show a particular distinguished SPF performance and UVA photoprotection boosting effect, , as it is demonstrated by the following examples.
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the first aspect of the present invention is further characterized in that it does not contain one or more of the following mycosporine-like amino acid compounds: compound 1: 230145 compound 4: compound 5: 230145 compound 8: compound 9: 230145 [0301]
- mycosporine-like amino acid compounds (b) as described herein contain one or more chiral centers, and, thus, can exist as racemic mixtures of enantiomers, mixtures of diastereomers or enantiomerically or optically pure compounds. It should also be noted the compounds of the invention include E and Z isomers, or a mixture thereof, and cis and trans isomers or a mixture thereof.
- the chemical structures of general formulae (V) to (X) and their variants and compounds explicitly disclosed herein include all possible enantiomers and diastereomers or stereoisomers.
- the mycosporine-like amino acid compounds (b) used according to the present invention are isolated as either the E or Z isomer.
- the compounds of the invention are a mixture of the E and Z isomers.
- stereomerically pure compounds are used in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention.
- stereomerically pure means that one stereoisomer of a compound is substantially free of other stereoisomers of that compound or one geometric isomer (e.g., about a double 230145 bond) is substantially free of the other geometric isomer.
- a stereomerically pure compound of the invention having one chiral center will be substantially free of the opposite enantiomer of the compound.
- a stereomerically pure compound of the invention having two chiral centers, or a composition thereof will be substantially free of other diastereomers of the compound.
- a stereomerically pure compound of the invention having a double bond capable of E/Z isomerism, or a composition thereof will be substantially free of one of the E/Z isomers.
- a typical stereomerically pure compound comprises greater than about 80 % by weight of one stereoisomer or E/Z isomer of the compound and less than about 20 % by weight of other stereoisomers or E/Z isomer of the compound, more preferably greater than about 90 % by weight of one stereoisomer or E/Z isomer of the compound and less than about 10 % by weight of the other stereoisomers or E/Z isomer of the compound, even more preferably greater than about 95 % by weight of one stereoisomer or E/Z isomer of the compound and less than about 5 % by weight of the other stereoisomers or E/Z isomer of the compound, and most preferably greater than about 97 % by weight of one stereoisomer or E/Z isomer of the compound and less than about 3 % by weight of the other stereoisomers or E/Z isomer of the compound.
- stereomerically enriched means a compound of the invention, or a composition thereof, that comprises greater than about 60 % by weight of one stereoisomer or E/Z isomer of a compound of the invention, preferably greater than about 70 % by weight, more preferably greater than about 80 % by weight of one stereoisomer or E/Z isomer of a compound of the invention.
- mycosporine-like amino acid compound according to the general formulae (V) to (X) and their variants as well as individual mycosporine-like amino acid compounds specified herein are to be interpreted as encompassing racemic mixtures of enantiomers, mixtures of diastereomers or enantiomerically or optically pure compounds.
- the mycosporine-like amino acid compounds according to general formulae (V) to (X) and their variants are in equilibrium with their tautomer structures, in which the hydrogen of the amino group changes its places with the double bond of the cyclohexene ring.
- Tautomerism is defined as each of two or more isomers of a compound which exist together in equilibrium and are readily interchanged by migration of an atom or group within the molecule. Tautomeric pure or enriched systems will readily interchange into the equilibrium state over time.
- the tautomers of general formula (V) are represented by general formulae (V- tau): formula (V) formula (V-tau).
- the tautomers of general formula (VI) are represented by general formula (VI- tau): " formula (VI) formula (VI-tau). 230145 [0312]
- the above principles of tautomerism and redeposition explained on the basis of the mycosporine-like amino acid compounds according to the general formula (V) and (VI) are likewise applicable with respect to any of the mycosporine-like amino acid compounds defined by the general formulae (VII), (VIII), (IX), (X) and their variants or with respect to any individual mycosporine-like amino acid compounds specified herein.
- mycosporine-like amino acid compound represented by any of the general formulae (V) to (X) and their variants or to an individual mycosporine-like amino acid compound specified herein encompasses likewise its tautomer isomer(s).
- the mycosporine-like amino acid compounds according to the general formulae (V) to (X) and their variants as well as individual mycosporine-like amino acid compounds specified herein are used according to the first aspect of the present invention either in neutral, i.e. uncharged form, or in the form of their salts, such as an acid addition salt, with inorganic or organic acids.
- salt in the context of the present invention refers to a salt of a compound that possesses the desired effect or pharmacological activity of the parent compound.
- Such salts include: (1) acid addition salts formed with inorganic acids, or formed with organic acids, preferably monovalent or polyvalent carboxylic acids; or (2) salts formed when an acidic proton present in the starting compound is replaced by a metal ion, e.g., an alkali metal ion, an alkaline earth ion, or an aluminium ion; or coordinated with an organic base.
- the mycosporine-like amino acid compounds according to the general formulae (V) to (X) and their variants or the mycosporine-like amino acid compounds specified herein comprise a protonable N atom.
- the inorganic acids that form acid addition salts with the mycosporine-like amino acid compounds are preferably selected from the group consisting of hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid and the like. Particularly preferred is the hydrochloride salt or the sulfate salt or the phosphate salt.
- Even more preferred are acid addition salts with organic mono- or polycarboxylic acids.
- acid addition salts with organic mono- or polycarboxylic acids wherein the carboxylic acid is selected from saturated or mono- or polyunsaturated C1 to C30 monocarboxylic acids, saturated or mono- or polyunsaturated C3 to 10 di- or tricarboxylic acids.
- the carboxylic acid may be mono- or poly-substituted with hydroxy groups, preferably ⁇ -hydroxycarboxylic acids in which the hydroxy group is located on the carbon atom adjacent to the carboxy group. Many representatives occur naturally as so- called fruit acids.
- Preferred ⁇ -hydroxycarboxylic acids are: malic acid, citric acid, 2- hydroxy-4-methylmercaptobutyric acid, glycolic acid, isocitric acid, mandelic acid, lactic acid, tartronic acid, or tartaric acid.
- the organic acids that form acid addition salts with the mycosporine-like amino- acid compounds are preferably selected from the group consisting of amino acids, acetic acid, trifluoroacetic acid, propionic acid, hexanoic acid, cyclopentane propionic acid, glycolic acid, pyruvic acid, lactic acid, malonic acid, oxalic acid, succinic acid, malic acid, maleic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, 3-(4- hydroxybenzoyl)benzoic acid, cinnamic acid, mandelic acid, methanesulfonic acid, ethanesulfonic acid, 1,2-ethanedisulfonic acid, 2-hydroxyethanesulfonic acid, benzenesulfonic acid, 4-chlorobenzenesulfonic acid, 2-naphthalenesulfonic acid, 4- toluenesulfonic acid, camphorsulf
- Suitable anionic counterions are in particular chloride, bromide, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C1- to 230145 C4-alkanoic acids, preferably formate, acetate, trifluoroacetate, propionate and butyrate, furthermore lactate, gluconate, and the anions of poly acids such as succinate, oxalate, maleate, fumarate, malate, tartrate and citrate, furthermore sulfonate anions such as besylate (benzenesulfonate), tosylate (p-toluenesulfonate), napsylate (naphthalene-2- sulfonate), mesylate (methanesulfonate), esylate (e
- the metal ions for salt formation that replace an acidic proton present in the starting compound are selected from the group consisting of alkali metal ions, preferably Na+, K+, or Li+, alkaline earth metal ions, preferably Ca++ or Mg++, aluminium+++, or NH4+.
- the coordinating organic base for salt formation is selected from the group consisting of ethanolamine, diethanolamine, triethanolamine, N-methylglucamine, triethylamine, and the like.
- mycosporine-like amino acid compound includes both the neutral, uncharged form of the compound/molecule and equally the salt form of the compound.
- the salt form of the mycosporine-like amino acid compounds leads to a lower logPOW and, thus, making the compounds more hydrophilic, which results in a better water solubility.
- the cationic salts of the mycosporine-like amino acid compounds support emulsification processes in emulsions, due to their surface active, i.e. co- emulsifying, properties.
- the cationic salt form of the mycosporine-like compounds shows excellent substantivity behaviour on skin and hair: most conditioning actives are cationic; the conditioning effect leads to a softer skin feel, which makes the end products more accepted by the consumer.
- the mycosporine-like amino acid compounds in the cationic salt form exhibit antimicrobial activity.
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the first aspect of the present invention comprises one of the following combinations of components (a) and (b): ⁇ at least one inorganic UV-filter: titanium dioxide (TiO2) (amorphous or crystallized in rutile and/or anatase form) and/or zinc oxide (ZnO) and/or iron oxide (Fe2O3) and/or zirconium oxide (ZrO2) and/or silicon dioxide (SiO2) and/or manganese oxide (e.g.
- inorganic UV-filters in the form of non-nano pigments, nano pigments, treated non- nano pigments, and treated nano pigments, combined with at least one compound according to the general formula (V) as defined herein; or ⁇ at least one inorganic UV-filter: titanium dioxide (TiO2) (amorphous or crystallized in rutile and/or anatase form) and/or zinc oxide (ZnO) and/or iron oxide (Fe2O3) and/or zirconium oxide (ZrO 2 ) and/or silicon dioxide (SiO 2 ) and/or manganese oxide (e.g.
- inorganic UV-filters in the form of non-nano pigments, nano pigments, treated non- nano pigments, and treated nano pigments, combined with at least one compound according to the general formula (VI) as defined herein.
- inorganic UV-filter and a mycosporine-like amino acid compound show a synergistic SPF performance and UVA photoprotection improving effect of the sunscreen products, cosmetic or pharmaceutical preparation or homecare product.
- More preferred combinations of component (a) and (b) in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the first aspect of the present invention are: 230145 ⁇ at least one inorganic UV-filter: titanium dioxide (TiO2) (amorphous or crystallized in rutile and/or anatase form) and/or zinc oxide (ZnO) and/or iron oxide (Fe2O3) and/or zirconium oxide (ZrO2) and/or silicon dioxide (SiO2) and/or manganese oxide (e.g.
- MnO aluminium oxide
- Al2O3 aluminium oxide
- Ce2O3 cerium oxide
- BaCO3 barium carbonate
- CaCO3 calcium carbonate
- MnO aluminium oxide
- Al2O3 aluminium oxide
- Ce2O3 cerium oxide
- BaCO3 barium carbonate
- CaCO3 calcium carbonate
- MnO aluminium oxide
- Al2O3 aluminium oxide
- Ce2O3 cerium oxide
- BaCO3 barium carbonate
- CaCO3 calcium carbonate
- inorganic UV-filters in the form of non-nano pigments, nano pigments, treated non- nano pigments, and treated nano pigments, combined with MAA-4; or 230145 ⁇ at least one inorganic UV-filter: titanium dioxide (TiO2) (amorphous or crystallized in rutile and/or anatase form) and/or zinc oxide (ZnO) and/or iron oxide (Fe2O3) and/or zirconium oxide (ZrO2) and/or silicon dioxide (SiO2) and/or manganese oxide (e.g.
- MnO aluminium oxide
- Al2O3 aluminium oxide
- Ce2O3 cerium oxide
- BaCO3 barium carbonate
- CaCO3 calcium carbonate
- MnO aluminium oxide
- Al2O3 aluminium oxide
- Ce2O3 cerium oxide
- BaCO3 barium carbonate
- CaCO3 calcium carbonate
- MnO aluminium oxide
- Al2O3 aluminium oxide
- Ce2O3 cerium oxide
- BaCO3 barium carbonate
- CaCO3 calcium carbonate
- inorganic UV-filters in the form of non-nano pigments, nano pigments, treated non- nano pigments, and treated nano pigments, combined with MAA-8; or 230145 ⁇ at least one inorganic UV-filter: titanium dioxide (TiO2) (amorphous or crystallized in rutile and/or anatase form) and/or zinc oxide (ZnO) and/or iron oxide (Fe2O3) and/or zirconium oxide (ZrO2) and/or silicon dioxide (SiO2) and/or manganese oxide (e.g.
- MnO aluminium oxide
- Al2O3 aluminium oxide
- Ce2O3 cerium oxide
- BaCO3 barium carbonate
- CaCO3 calcium carbonate
- MnO aluminium oxide
- Al2O3 aluminium oxide
- Ce2O3 cerium oxide
- BaCO3 barium carbonate
- CaCO3 calcium carbonate
- MnO aluminium oxide
- Al2O3 aluminium oxide
- Ce2O3 cerium oxide
- BaCO3 barium carbonate
- CaCO3 calcium carbonate
- inorganic UV-filters in the form of non-nano pigments, nano pigments, treated non- nano pigments, and treated nano pigments, combined with MAA-13; or 230145 ⁇ at least one inorganic UV-filter: titanium dioxide (TiO2) (amorphous or crystallized in rutile and/or anatase form) and/or zinc oxide (ZnO) and/or iron oxide (Fe2O3) and/or zirconium oxide (ZrO2) and/or silicon dioxide (SiO2) and/or manganese oxide (e.g.
- MnO aluminium oxide
- Al2O3 aluminium oxide
- Ce2O3 cerium oxide
- BaCO3 barium carbonate
- CaCO3 calcium carbonate
- MnO aluminium oxide
- Al2O3 aluminium oxide
- Ce2O3 cerium oxide
- BaCO3 barium carbonate
- CaCO3 calcium carbonate
- inorganic UV-filters in the form of non-nano pigments, nano pigments, treated non- nano pigments, and treated nano pigments, combined with MAA-17; or ⁇ at least one inorganic UV-filter: titanium dioxide (TiO2) (amorphous or crystallized in rutile and/or anatase form) and/or zinc oxide (ZnO) and/or iron oxide (Fe2O3) and/or zirconium oxide (ZrO2) and/or silicon dioxide (SiO2) and/or manganese oxide (e.g.
- inorganic UV-filters in the form of non-nano pigments, nano pigments, treated non- nano pigments, and treated nano pigments, combined with MAA-20; or 230145 ⁇ at least one inorganic UV-filter: titanium dioxide (TiO2) (amorphous or crystallized in rutile and/or anatase form) and/or zinc oxide (ZnO) and/or iron oxide (Fe2O3) and/or zirconium oxide (ZrO2) and/or silicon dioxide (SiO2) and/or manganese oxide (e.g.
- MnO aluminium oxide
- Al2O3 aluminium oxide
- Ce2O3 cerium oxide
- BaCO3 barium carbonate
- CaCO3 calcium carbonate
- MnO aluminium oxide
- Al2O3 aluminium oxide
- Ce2O3 cerium oxide
- BaCO3 barium carbonate
- CaCO3 calcium carbonate
- MnO aluminium oxide
- Al2O3 aluminium oxide
- Ce2O3 cerium oxide
- BaCO3 barium carbonate
- CaCO3 calcium carbonate
- inorganic UV-filters in the form of non-nano pigments, nano pigments, treated non- nano pigments, and treated nano pigments, combined with MAA-24; or 230145 ⁇ at least one inorganic UV-filter: titanium dioxide (TiO2) (amorphous or crystallized in rutile and/or anatase form) and/or zinc oxide (ZnO) and/or iron oxide (Fe2O3) and/or zirconium oxide (ZrO2) and/or silicon dioxide (SiO2) and/or manganese oxide (e.g.
- inorganic UV-filters in the form of non-nano pigments, nano pigments, treated non- nano pigments, and treated nano pigments, combined with MAA-25; or ⁇ at least one inorganic UV-filter: titanium dioxide (TiO2) (amorphous or crystallized in rutile and/or anatase form) and/or zinc oxide (ZnO) and/or iron oxide (Fe2O3) and/or zirconium oxide (ZrO2) and/or silicon dioxide (SiO2) and/or manganese oxide (e.g.
- MnO aluminium oxide
- Al2O3 aluminium oxide
- Ce2O3 cerium oxide
- BaCO3 barium carbonate
- CaCO3 calcium carbonate
- MnO aluminium oxide
- Al2O3 aluminium oxide
- Ce2O3 cerium oxide
- BaCO3 barium carbonate
- CaCO3 calcium carbonate
- inorganic UV-filters in the form of non-nano pigments, nano pigments, treated non- nano pigments, and treated nano pigments, combined with MAA-28; or 230145 ⁇ at least one inorganic UV-filter: titanium dioxide (TiO2) (amorphous or crystallized in rutile and/or anatase form) and/or zinc oxide (ZnO) and/or iron oxide (Fe2O3) and/or zirconium oxide (ZrO2) and/or silicon dioxide (SiO2) and/or manganese oxide (e.g.
- MnO aluminium oxide
- Al2O3 aluminium oxide
- Ce2O3 cerium oxide
- BaCO3 barium carbonate
- CaCO3 calcium carbonate
- MnO aluminium oxide
- Al2O3 aluminium oxide
- Ce2O3 cerium oxide
- BaCO3 barium carbonate
- CaCO3 calcium carbonate
- MnO aluminium oxide
- Al2O3 aluminium oxide
- Ce2O3 cerium oxide
- BaCO3 barium carbonate
- CaCO3 calcium carbonate
- inorganic UV-filters in the form of non-nano pigments, nano pigments, treated non- nano pigments, and treated nano pigments, combined with MAA-32; or 230145 ⁇ at least one inorganic UV-filter: titanium dioxide (TiO2) (amorphous or crystallized in rutile and/or anatase form) and/or zinc oxide (ZnO) and/or iron oxide (Fe2O3) and/or zirconium oxide (ZrO2) and/or silicon dioxide (SiO2) and/or manganese oxide (e.g.
- MnO aluminium oxide
- Al2O3 aluminium oxide
- Ce2O3 cerium oxide
- BaCO3 barium carbonate
- CaCO3 calcium carbonate
- MnO aluminium oxide
- Al2O3 aluminium oxide
- Ce2O3 cerium oxide
- BaCO3 barium carbonate
- CaCO3 calcium carbonate
- MnO aluminium oxide
- Al2O3 aluminium oxide
- Ce2O3 cerium oxide
- BaCO3 barium carbonate
- CaCO3 calcium carbonate
- inorganic UV-filters in the form of non-nano pigments, nano pigments, treated non- nano pigments, and treated nano pigments, combined with MAA-36; or 230145 ⁇ at least one inorganic UV-filter: titanium dioxide (TiO2) (amorphous or crystallized in rutile and/or anatase form) and/or zinc oxide (ZnO) and/or iron oxide (Fe2O3) and/or zirconium oxide (ZrO2) and/or silicon dioxide (SiO2) and/or manganese oxide (e.g.
- MnO aluminium oxide
- Al2O3 aluminium oxide
- Ce2O3 cerium oxide
- BaCO3 barium carbonate
- CaCO3 calcium carbonate
- MnO aluminium oxide
- Al2O3 aluminium oxide
- Ce2O3 cerium oxide
- BaCO3 barium carbonate
- CaCO3 calcium carbonate
- MnO aluminium oxide
- Al2O3 aluminium oxide
- Ce2O3 cerium oxide
- BaCO3 barium carbonate
- CaCO3 calcium carbonate
- the combinations with the mycosporine-like amino acid compounds and an inorganic UV-filter show a synergistic SPF performance and UVA photoprotection improving effect.
- This SPF performance and UVA photoprotection improving effect can especially be observed when the mycosporine-like amino acid is in its acid or in its salt form, i.e. in its cationic form.
- the synergistic SPF performance and UVA photoprotection improving effect is especially pronounced for the mycosporine-like amino acid compounds MAA-1 or MAA-13 and MAA-20 to MAA-39, when combined with any of the inorganic UV-filter.
- the compounds defined herein may be used in combination with further UV-absorbing agents, which are different from the at least one inorganic UV-filter (a), in order to further optimize the SPF, i.e.
- the at least inorganic UV-filter (a) in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product as defined herein is advantageously combined with at least one primary organic UV-filter and/or with at least one secondary sun protection ingredient or secondary sun protection UV-filter.
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the invention advantageously contains at least one further primary organic UVA filter and/or UVB filter and/or a broadband filter for their use in stopping UV radiation.
- Non-limiting examples of such primary organic UV-filters include: (i) sparingly soluble UV-filters (not appreciably soluble in either water or oil) such as Methylene Bis-Benzotriazolyl Tetramethylbutylphenol, Tris- Biphenyl Triazine, Methanone, 1,1'-(1,4-piperazinediyl)bis[1-[2-[4-(diethylamino)-2-hydroxybenzoyl- ]phenyl]; (ii) oil soluble organic UV-filters (at least partially soluble in oil or organic solvent), such as Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine, Butyl Methoxydibenzoylmethane (BMBM), Oxybenzone, Sulisobenzone, Diethylhexyl Butamido Triazone (DBT), Drometrizole Trisiloxane, Ethylhexyl Methoxycinnamate (E) sparing
- Benzophenones a. Benzophenone-3 (BP3) b. Benzophenone-4 (BP4) (3) Salicylates a. Homosalate (HMS) b. 2-ethylhexyl salicylate (EHS) (4) p-Aminobenzoic acid and derivatives a. Ethylhexyl dimethyl PABA (OD-PABA) b. 4-p-aminobenzoic acid (PABA) (5) Benzimidazole derivatives a. Phenylbenzimidazole sulfonic acid (PMDSA) b.
- HMS Homosalate
- EHS 2-ethylhexyl salicylate
- PABA 4-p-aminobenzoic acid
- PMDSA Phenylbenzimidazole sulfonic acid
- Cinnamates a. Ethylhexyl methoxycinnamate (OMC) b. Isoamyl p-methoxycinnamate (IMC, amiloxate) (10) Camphor derivatives a. Terephtalydene dicamphor sulfonic acid (PDSA) 230145 b. 3-benzylidene camphor (3BC) c. Benzylidene camphor sulfonic acid (BCSA) d. 4-methylbenzylidene camphor (4-MBC) e.
- OMC Ethylhexyl methoxycinnamate
- IMC Isoamyl p-methoxycinnamate
- Camphor derivatives a. Terephtalydene dicamphor sulfonic acid (PDSA) 230145 b. 3-benzylidene camphor (3BC) c. Benzylidene camphor sulfonic acid (BCSA)
- the UV-filter is one or more of a para-aminobenzoic acid derivative, a salicylic derivative, a cinnamic derivative, a benzophenone or an aminobenzophenone, an anthranillic derivative, a b,b-diphenylacrylate derivative, a benzylidenecamphor derivative, a phenylbenzimidazole derivative, a benzotriazole derivative, a triazine derivative, a bisresorcinyl triazine, an imidazoline derivative, a benzalmalonate derivative, a 4,4-diarylbutadiene derivative, a benzoxazole derivative, a merocyanine, malonitrile or a malonate diphenyl butadiene derivative, a chalcone, and
- the at least one primary organic UV-filter is preferably selected from the group consisting of Camphor Benzalkonium Methosulfate, Homosalate, Benzophenone-3, Phenylbenzimidazole Sulfonic Acid, Terephthalylidene Dicamphor Sulfonic Acid, Butyl Methoxydibenzoylmethane, Benzylidene Camphor Sulfonic Acid, Octocrylene, Polyacrylamidomethyl Benzylidene Camphor, Ethylhexyl Methoxycinnamate, PEG-25 PABA, Isoamyl p-Methoxycinnamate, Ethylhexyl Triazone, Drometrizole Trisiloxane, Diethylhexyl Butamido Triazone, 4-Methylbenzylidene Camphor, Ethylhexyl Salicylate, Ethylhexyl Dimethyl PABA, Benzophenone-4,
- the at least one primary organic UV-filter is selected from the group consisting of Camphor Benzalkonium Methosulfate, Benzophenone-3, 230145 Terephthalylidene Dicamphor Sulfonic Acid, Benzylidene Camphor Sulfonic Acid, Polyacrylamidomethyl Benzylidene Camphor, PEG-25 PABA, Drometrizole Trisiloxane, Ethylhexyl Dimethyl PABA, Benzophenone-4, Benzophenone-5, Methylene Bis- Benzotriazolyl Tetramethylbutylphenol, Polysilicone-15, Titanium Dioxide (nano), Tris- biphenyl triazine (nano), Phenylene Bis-Diphenyltriazine, Methoxypropylamino Cyclohexenylidene Ethoxyethylcyanoacetate, Bis-(Diethylaminohydroxybenzoyl Benzoyl) Piperaz
- the at least one primary organic UV-filter is selected from the group consisting of Homosalate, Phenylbenzimidazole Sulfonic Acid, Butyl Methoxydibenzoylmethane, Octocrylene, Ethylhexyl Methoxycinnamate, Isoamyl p- Methoxycinnamate, Ethylhexyl Triazone, Diethylhexyl Butamido Triazone, 4- Methylbenzylidene Camphor, Ethylhexyl Salicylate, Disodium Phenyl Dibenzimidazole Tetrasulfonate, Bis-Ethylhexyloxyphenol Methoxyphenyl Triazine, Diethylamino Hydroxy benzoyl Hexyl Benzoate, Menthyl Anthranilate, and any mixture thereof.
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention comprises at least one UVA filter and at least one UVB filter.
- Such sunscreen products, cosmetic or pharmaceutical preparations or homecare products according to the present invention provide broad- spectrum photo protection, i.e. protection from both UVA and UVB.
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention comprises a combination with one or more broadband filters which are selected from the group consisting of 2-ethylhexyl-2-cyano-3,3-diphenyl acrylate, ethyl-2-cyano-3,3'-diphenyl 230145 acrylate, dihydroxy-4-methoxybenzophenone, 2,4-dihydroxybenzophenone, tetrahydroxy benzophenone, 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, 2-hydroxy-4-n- octoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, sodium hydroxymethoxy benzophenone sulfonate, disodium-2,2'-dihydroxy-4,4'-dimethoxy-5,5'- disulfobenzophenone, phenol, 2-(2H-benzotriazol-2-yl)-4-methyl-6
- the primary organic UV-filters cited before which can be used in the context of the present invention are preferred but naturally are not limiting.
- the aforesaid primary organic UV-filters are used in the sunscreen or cosmetic or pharmaceutical preparation either as a single component or comprises at least two, more preferably at least three, most preferably at least four or even more different UV- filters.
- the combination of effective sun protection UV-filters of different categories such as UVA filter, UVB, broadband filter, inorganic pigments provides reliable protection against the different UV rays in the wavelength range of 290 to 400 nm.
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the invention contains the primary organic and/or inorganic UV-filters, in a total amount so that the product or preparation according to the invention has a sun protection factor SPF of 6 to 100, preferably 6 to 70.
- SPF sun protection factor
- Such compositions according to the invention are particularly suitable for protecting the skin, hair and nails.
- secondary sun protection ingredients of the antioxidant type may also be advantageously used in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention in order to further optimize UV protection.
- Secondary sun protection ingredients of the antioxidant type interrupt the photochemical reaction chain which is initiated when UV rays penetrate into the skin.
- secondary sun protection ingredients are amino acids (for example arginine, lysine, glycine, histidine, tyrosine, tryptophane) and derivatives thereof, imidazoles (for example urocanic acid) and derivatives thereof, peptides, such as D,L- carnosine, D-carnosine, L-carnosine and derivatives thereof (for example anserine), 230145 carotenoids, carotenes (for example alpha-carotene, beta-carotene, lycopene) and derivatives thereof, chlorogenic acid and derivatives thereof, liponic acid and derivatives thereof (for example dihydroliponic acid), aurothioglucose, propylthiouracil and other thiols (for example thioredoxine, glutathione, cysteine, cystine, cystamine and glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, but
- the group of secondary sun protection ingredients also encompasses plant- based extract(s).
- Said plant-based extracts have antioxidative and in general photoprotective properties and interrupt the photochemical reaction chain which is initiated when UV rays penetrate into the skin, thus, are effective in preventing skin aging.
- the plant extracts with UV protection properties are selected from the group consisting 230145 of Lignin/Cellulose, Lignin, Lignin Hydrolyzed, Propolis and green propolis, Galanga Extract, macro and micro algae (Porphyra, red algae (Porphyra Umbilicalis), Palmaria palmata, Saccharina latissimi, Corallina pilulifera, Eckloina cava, Sargassum sagamianum, Porphyra rosengurttii, Sargassum siliquastrum, Thalassiosira weissflogii, Green Microalgae (e.g. Interfilum and Klebsormidium), Seaweed (e.g.
- the plant extracts with UV protection properties are selected from the group consisting of Lignin/Cellulose, Lignin, Lignin Hydrolyzed, Galanga Extract, Porphyra, red algae (Porphyra Umbilicalis), Green Microalgae (e.g.
- the amount of secondary sun protection substances in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention is advantageously from 0.005 to 5.0 % by weight, preferably 0.01 to 4.0 % by weight, and most preferred 0.05 to 3.0 % by weight, based on the total weight of the ready-to-use formulation.
- the UV-filters are incorporated either in the aqueous or in the lipophilic part of the sunscreen product, cosmetic or pharmaceutical preparation or homecare product, depending on whether they are water or oil (fat) soluble/miscible UV-filters or may even be added to the final product by standard methods known to a person skilled in the art.
- the at least one inorganic UV-filter (a) according to the first aspect of the present invention is present in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product in an amount of 0.5 to 60.0 % by weight, based on the total weight of the final formulation.
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprises the inorganic UV-filter (a) in an amount of 0.3 to 55.0 % by weight, based on the total weight of the final formulation.
- the inorganic UV-filter (a) is advantageously used in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product in an amount of 0.1 to 50.0 % by weight, based on the total weight of the final formulation.
- the inorganic UV-filter is advantageously used in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product in an amount of 1.0 to 45.0 % by weight, based on the total weight of the final formulation.
- the above amounts relate to the total content of the inorganic UV-filters in the mixture, i.e. the amount is the sum of the content of all inorganic UV-filters in the mixture.
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprises the inorganic UV-filter (a) and the further primary and secondary UV-protection components as defined herein in an amount of 0.3 to 80.0 % by weight, based on the total weight of the final formulation.
- the inorganic UV-filter (a) and the further primary and secondary UV-protection components as defined herein are advantageously used in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product in an amount of 0.5 to 75.0 % by weight, based on the total weight of the final formulation.
- the above amounts relate to the sum of the content of all UV-filters/UV protection components present in the sunscreen or cosmetic, pharmaceutical or homecare preparation.
- the at least one mycosporine-like amino acid compound (b) according to the first aspect of the present invention is present in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product in an amount of 0.001 to 15.0 % by weight, based on the total weight of the final formulation.
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprises the at least one mycosporine-like amino acid compound (b) in an amount of 0.01 to 10.0 % by weight, based on the total weight of the final formulation.
- the at least one mycosporine-like amino acid compound (b) is advantageously used in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product in an amount of at 0.05 to 7.5 % by weight, based on the total weight of the final formulation.
- the at least one mycosporine-like amino acid compound (b) is advantageously used in the sunscreen product, cosmetic or 230145 pharmaceutical preparation or homecare product in an amount of at 0.1 to 5.0 % by weight, based on the total weight of the final formulation.
- the above amounts relate to the total content of the mycosporine-like amino acid compounds in the mixture, i.e. the amount is the sum of the content of all mycosporine-like amino acid compounds (b) in the mixture.
- the sunscreen product according to the first aspect of the present invention comprises (i) 0.5 to 60.0 % by weight of at least one inorganic UV-filter; and (ii) 0.001 to 15.0 % by weight of at least one mycosporine-like amino acid compound as defined herein; based on the based on the total weight of the final formulation.
- the cosmetic or pharmaceutical preparation according to the first aspect of the present invention comprises (iii) 1.0 to 45.0 % by weight of at least one inorganic UV-filter; and (iv) 0.1 to 5.0 % by weight of at least one mycosporine-like amino acid compound as defined herein; based on the based on the total weight of the final formulation.
- the sunscreen products, cosmetic or pharmaceutical preparations or homecare products according to the present invention provide broad-spectrum photo-protection to skin und therefore provide protection from both UVA and UVB radiation.
- Sun protection factor is a measure of UVB protection as described above.
- the compositions of the present invention have an SPF of at least 6. The SPF however, can vary as needed.
- the type and amount of UVA and UVB filters can be varied to obtain a desired level of SPF.
- the SPF (UVB) of the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention is at least 6, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80 or even more.
- the SPF (UVA) or UVA SP of the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention is 1 to 50, preferably at least 10 and most preferred more than 2.
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the first aspect of the present invention it is also possible and in some cases advantageous to combine the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the first aspect of the present invention with other customary active substances, adjuvants or additives, customarily used for sunscreen products, cosmetic or pharmaceutical compositions or homecare products, as further described below, in order to obtain a ready-for-use preparation or formulation.
- the other active agents and/or adjuvants and/or additives or auxiliaries are for example abrasives, anti-acne agents, agents against ageing of the skin, anti-cellulitis agents, anti-dandruff agents, anti-inflammatory agents, irritation-preventing agents, irritation-inhibiting agents, antioxidants, alkanediols, astringents, odour absorbers, perspiration-inhibiting agents, antiseptic agents, anti-statics, antimicrobial agents, binders, buffers, carrier materials, oil components, chelating agents, cell stimulants, cleansing agents, depilatory agents, surface-active substances, deodorizing agents, antiperspirants, softeners, emulsifiers, enzymes, enzyme inhibitors, essential oils, fibres, film-forming agents, water resistance improving agents fixatives, foam-forming agents, foam stabilizers, substances for preventing foaming, foam boosters, gelling agents, gel- forming agents, hair care agents, hair-setting agents, hair-
- Carriers The sunscreen products, cosmetic or pharmaceutical, in particular dermatological, preparations or homecare products as defined herein, in the form of ointments, pastes, creams and gels, etc., are preferably based on a carrier. Most common acceptable carrier is water. Acceptable carriers other than water include glycerin, C1-4 alcohols, organic solvents, fatty alcohols, fatty ethers, fatty esters, polyols, glycols, vegetable oils, mineral oils, liposomes, laminar lipid materials, water, or a mixture thereof.
- Non-limiting examples of organic solvents include mono alcohols and polyols such as ethyl alcohol, isopropyl alcohol, propyl alcohol, benzyl alcohol, and phenylethyl alcohol, or glycols or glycol ethers such as, for example, monomethyl, monoethyl and monobutyl ethers of ethylene glycol, propylene glycol or ethers thereof such as, for example, monomethyl ether of propylene glycol, butylene glycol, hexylene glycol, dipropylene glycol as well as alkyl ethers of diethylene glycol, for example monoethyl ether or monobutyl ether of diethylene glycol.
- mono alcohols and polyols such as ethyl alcohol, isopropyl alcohol, propyl alcohol, benzyl alcohol, and phenylethyl alcohol
- glycols or glycol ethers such as, for example, monomethyl, monoethyl and monobutyl ether
- organic solvents are ethylene glycol, propylene glycol, butylene glycol, hexylene glycol, propane diol, and glycerin.
- the organic solvents can be volatile or non-volatile compounds.
- the total amount of carrier in the compositions can vary but is typically 40 to 90 % by weight, based on the total weight of the composition.
- the compositions of the present invention may include at least one water-soluble or organic solvent.
- Non-limiting examples of organic solvents include monoalcohols and polyols such as ethyl alcohol, isopropyl alcohol, propyl alcohol, benzyl alcohol, and phenylethyl alcohol, or glycols or glycol ethers such as, for example, monomethyl, monoethyl and monobutyl ethers of ethylene glycol, propylene glycol or ethers thereof such as, for example, monomethyl ether of propylene glycol, butylene glycol, hexylene glycol, dipropylene glycol as well as alkyl ethers of diethylene glycol, for example monoethyl ether or monobutyl ether of diethylene glycol.
- monoalcohols and polyols such as ethyl alcohol, isopropyl alcohol, propyl alcohol, benzyl alcohol, and phenylethyl alcohol
- glycols or glycol ethers such as, for example, monomethyl, monoethyl and monobut
- organic solvents are ethylene glycol, propylene glycol, butylene glycol, hexylene glycol, propane diol, and glycerin.
- the organic solvents can be volatile or non-volatile compounds.
- water-soluble solvents include alkanols (polyhydric alcohols such as glycols and polyols) such as glycerin, 1 ,2,6-hexanetriol, trimethylolpropane, ethylene glycol, propylene glycol, diethylene glycol, butylene glycol, hexylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, dipropylene glycol, 1,3-butanediol, 2,3-butanediol, 1,4-butanediol, 3-methyl-1 ,3- butanediol, 1 ,5- pentanediol, tetraethylene glycol, 1,
- the total amount water-soluble or organic solvent(s) in the composition according to the present invention may vary but is typically 0.1 to 50 % by weight, based on the total weight of the composition.
- Solubilizing agents are compounds that help solubilize the UV-filter(s) and/or other components in the compositions.
- a particularly useful but non limiting example of a solubilizing agent is a hydrotrope. Hydrotropes (or hydrotropic agents) are a diverse class of typically water-soluble compounds that may be characterized by an amphiphilic molecular structure and an ability to dramatically increase the solubility of poorly soluble organic molecules in water.
- Non-limiting examples of hydrotopes include sodium 1 ,3-benzenedisulfonate, sodium benzoate, sodium 4- pyridinecarboxylate, sodium salicylate, sodium benzene sulfonate, caffeine, sodium p- toluene sulfonate, sodium butyl monoglycolsulfate, 4- aminobenzoic acid HCI, sodium cumene sulfonate, N,N-diethylnicotinamide, N-picolylnicotinamide, N-allylnicotinamide, 2-methacryloyloxyethyl phosphorylcholine, resorcinol, butylurea, pyrogallol, N- picolylacetamide 3.5, procaine HCI, proline HCI, nicotinamide, pyridine, 3-picolylamine, sodium ibuprofen, sodium xylenesulfonate, ethyl carbamate, pyridoxal
- particularly useful hydrotropes include nicotinamide (niacinamide), caffeine, sodium PCA, sodium salicylate, urea, and dihydroxyethyl urea, in particular, nicotinamide (niacinamide) and/or caffeine.
- nicotinamide niacinamide
- a combination of two or more, three or more, or four or more hydrotopes may also be used in the compositions according to the present invention.
- the total amount of solubilizing agent(s) in the compositions of the present invention may vary but are typically in an amount of 0.01 to 20 wt.%, based on the total weight of the composition.
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product may include at least one oil phase or at least one oil component, waxes, starch, tragacanth, cellulose derivatives, polyethylene glycols, silicones, bentonites, silica, talc and zinc oxide or any mixture thereof.
- Powders include carriers such as lactose, talc, silica, aluminium hydroxide, calcium silicate and polyamide powder or any mixture thereof.
- Solutions and emulsions include carriers such as solvents such as water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, propylene glycol, etc. or any mixture thereof.
- the oil phase or the oil component in the sunscreen product, cosmetic, pharmaceutical preparation or homecare product according to the present invention which may be suitable are for example plant oils, hydrocarbons, fatty alcohols, fatty acid esters, or mixtures of two or more of the aforesaid oil components.
- the oil phase or oil component in the sunscreen product, cosmetic, pharmaceutical preparation is preferably a plant oil and even more preferably a liquid plant oil. It can also advantageously be a mixture of two or more plant oils components, especially liquid plant oil mixtures.
- Plant oils or vegetable oils are oils extracted from seeds, or less often, from other parts of fruits. Like animal fats, plant oils are mixtures of triglycerides. Soybean oil, rapeseed oil and cocoa butter are examples of plant oils from seeds. Olive oil, palm oil 230145 and rice bran oil are examples of oils from other parts of fruits. In common usage, plant oil or vegetable oil may refer exclusively to vegetable fats which are liquid at room temperature or at 35 to 37 °C skin temperature. Vegetable oils are usually edible. [0372] The term “plant oils” also includes unsaturated plant oils. Unsaturated oils or vegetable oils can be transformed through partial or complete “hydrogenation” into oils of higher melting point.
- the hydrogenation process involves “sparging” the oil at high temperature and pressure with hydrogen in the presence of a catalyst, typically a powdered nickel compound. As each carbon-carbon double-bond is chemically reduced to a single bond, two hydrogen atoms each form single bonds with the two carbon atoms. The elimination of double bonds by adding hydrogen atoms is called saturation; as the degree of saturation increases, the oil progresses toward being fully hydrogenated.
- An oil may be hydrogenated to increase resistance to rancidity (oxidation) or to change its physical characteristics. As the degree of saturation increases, the oil's viscosity and melting point increase.
- the plant oil is selected from the group consisting of Persea Gratissima (Avocado Oil), Abies Alba Seed Oil, Acacia Victoriae Seed Oil, Actinidia Chinensis (Kiwi) Seed Oil, Amaranthus Hypochondriacus Seed Oil, Arachis Hypogaea (Peanut) Oil, Astrocaryum Murumuru Seed Butter, Astrocaryum Tucuma Seed Butter, Astrocaryum Tucuma Seed Oil, Astrocaryum Vulgare Fruit Oil, Astrocaryum Vulgare Kernel Oil, Avena Sativa (Oat) Kernel Oil, Brassica Alba Seed Oil, Brassica Campestris (Rapeseed) Seed Oil, Butyrospermum Parkii (Shea) Butter, Butyrospermum Parkii (Shea) Oil, Calendula Officinalis Seed Oil, Calophyllum Inophyllum Seed Oil, Calophyllum Tacamahaca
- Hydrocarbons are in general organic compounds consisting entirely of hydrogen and carbon. As defined by IUPAC nomenclature or organic chemistry, the classifications for hydrocarbons are: 1. Saturated hydrocarbons are the simplest of the hydrocarbon species. They are composed entirely of single bonds and are saturated with hydrogen. The formula for acyclic saturated hydrocarbons (i.e., alkanes) is C n H2 n +2. The most general form of saturated hydrocarbons is CnH2n+2(1-r), where r is the number of rings.
- Saturated hydrocarbons are the basis of petroleum fuels and are found as either linear or branched species.
- Unsaturated hydrocarbons have one or more double or triple bonds between carbon atoms. Those with double bond are called alkenes. Those with one double bond have the formula CnH2n (assuming non-cyclic structures). Those containing triple bonds are called alkynes. Those with one triple bond have the formula C n H2 n ⁇ 2.
- Aromatic hydrocarbons, also known as arenes, are hydrocarbons that have at least one aromatic ring.
- Hydrocarbons can be inter alia liquids (e.g.
- mineral oils and waxes are mixtures of predominantly saturated hydrocarbons consisting of straight ⁇ chain, branched and ring structures with carbon chain lengths greater than C14. Mineral oils and waxes are chemical substances prepared from naturally occurring crude petroleum oil. They mainly consist of mineral oil saturated hydrocarbons (MOSH) and mineral oil aromatic hydrocarbons (MOAH).
- Hydrocarbons have been used for many decades in skin and lip care cosmetic products due to their excellent skin tolerance as well as their high protecting and cleansing performance and broad viscosity options.
- mineral oils are non ⁇ allergenic since they are highly stable and not susceptible to oxidation or rancidity.
- a fatty alcohol (or long-chain alcohol) is usually a high-molecular-weight, straight- chain primary alcohol, but can also range from as few as 4 to 6 carbons to as many as 22 to 26, derived from natural fats and oils. The precise chain length varies with the source.
- Some commercially important fatty alcohols are lauryl, stearyl and oleyl alcohols.
- Fatty alcohols usually have an even number of carbon atoms and a single alcohol group (—OH) attached to the terminal carbon. Some are unsaturated and some are branched. Most fatty alcohols in nature are found as waxes which are esters with fatty acids and fatty alcohols. The traditional sources of fatty alcohols have largely been various vegetable oils and these remain a large-scale 230145 feedstock. The alcohols are obtained from the triglycerides (fatty acid triesters), which form the bulk of the oil. The process involves the transesterification of the triglycerides to give methyl esters which are then hydrogenated to give the fatty alcohols.
- Fatty alcohols are also prepared from petrochemical sources.
- ethylene is oligomerized using triethylaluminium followed by air oxidation.
- ethylene can be oligomerized to give mixtures of alkenes, which are subjected to hydroformylation, this process affording odd-numbered aldehyde, which is subsequently hydrogenated.
- Fatty alcohols are mainly used in the production of detergents and surfactants. They are components also of cosmetic solvents. They find use as co-emulsifiers, emollients and thickeners in cosmetics.
- the fatty alcohol is selected from the group consisting of phenyl propanol, dimethyl phenylbutanol, hexyldecanol, octyldodecanol, octyldecanol, tridecylalcohol, isostearyl alcohol, phenylisohexanol, phenylpropanol, trimethylbenzenepropanol, isoamylalcohol, isostearyl alcohol, and isotridecyl alcohol.
- the fatty alcohol is selected from the group consisting of hexyldecanol, octyldodecanol, phenylpropanol, isoamylalcohol, and mixtures of two or more of the aforesaid fatty alcohols.
- the fatty alcohol can be used either as a single component or in a mixture with one or more further different fatty alcohol(s) as specified above.
- a fatty acid ester is a type of ester that results from the combination of a fatty acid with an alcohol.
- the alcohol component is glycerol
- the fatty acid esters produced can be monoglycerides, diglycerides or triglycerides.
- Fatty acid esters have a conditioning effect of softening the skin to create a smoothing sensation. They are also added to cosmetics to dissolve high-polarity active ingredients and UV absorbers. Esters of straight-chain fatty acids and lower alcohols are effective for dissolving slightly soluble ingredients for oils with a light touch during application. Isostearic acids and other liquid oils with branched fatty acids and unsaturated fatty acids are commonly used as emollients. Higher fatty acid esters and esters of higher alcohols with relatively high melting points are added to skin creams to adjust the application touch.
- Oil bodies and emollients The sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention advantageously includes one or more oil bodies or emollients.
- An emollient is an oleaginous or oily substance which helps to smooth and soften the skin, and may also reduce its roughness, cracking or irritation.
- sunscreen products emollients keep the crystalline and oil-soluble organic and inorganic UV-filters solubilized and prevent them from recrystallisation.
- emollients function as wetting agents for inorganic UV-filters for a homogeneous dispersion in the formulations.
- Suitable oil bodies are, for example, Guerbet alcohols based on fatty alcohols having 6 to 18, preferably 8 to 10, carbon atoms, esters of linear C6-C22-fatty acids with linear or branched C6-C22-fatty alcohols or esters of branched C6-C 13-carboxylic acids with linear or branched C6-C22-fatty alcohols, such as, for example, myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl erucate, stearyl myristate, stearyl palmitate, stearyl stearate, stearyl isost
- esters of linear C6-C22-fatty acids with branched alcohols in particular 2-ethylhexanol
- esters of C18-C38- alkylhydroxy carboxylic acids with linear or branched C6-C22-fatty alcohols in particular Dioctyl Malate
- esters of linear and/or branched fatty acids with polyhydric alcohols such as, for example, propylene glycol, dimerdiol or trimertriol
- Guerbet alcohols triglycerides based on C6 -C10-fatty acids, liquid mono-/di-/triglyceride mixtures based on C6-C18-fatty acids
- esters of C6- C22- fatty alcohols and/or Guerbet alcohols with aromatic carboxylic acids in particular benzoic acid
- Finsolv® TN linear or branched, symmetrical or a symmetrical dialkyl ethers having 6 to 22 carbon atoms per alkyl group, such as, for example, dicaprylyl ether (Cetiol® OE), ring-opening products of epoxidized fatty acid esters with polyols, silicone oils (cyclomethicones, silicone methicone grades, etc.) and/or aliphatic or naphthenic hydrocarbons, such as, for example, squalane, squalene or dialkylcyclohexanes and any mixture thereof.
- Powders The compositions as defined herein may optionally include powders.
- the optional powders provide formulas that are smoother and softer on the skin.
- Representative powders include talc, mica, magnesium carbonate, calcium carbonate, magnesium silicate, aluminium magnesium silicate, silica, titanium dioxide, zinc oxide, red iron oxide, yellow iron oxide, black iron oxide, polyethylene powder, methacrylate powder, polystyrene powder, silk powder,
- Preferred solid powder materials which may be a component of the composition according to the invention are hydrocolloids, such as starches, degraded starches, chemically or physically modified starches, dextrins, (powdery) maltodextrins (preferably with a dextrose equivalent value of 5 to 25, preferably of 10 – 20), lactose, silicon dioxide, glucose, modified celluloses, gum arabic, ghatti gum, traganth, karaya, carrageenan, pullulan, curdlan, xanthan gum, gellan gum, guar flour, carob bean flour, alginates, agar
- Rheology modifiers The sunscreen product, cosmetic or pharmaceutical preparation or homecare products according to the present invention advantageously includes one or more thickening agents and/or rheology modifier.
- the rheology modifier is present in an amount that prevents significant dripping or pooling of the composition after application to the skin or to surfaces.
- the rheology modifier is a carbomer.
- the rheology modifier is selected from stearic acid, palmitic acid, stearyl alcohol, cetyl alcohol, behenyl alcohol, stearic acid, palmitic acid, the polyethylene glycol ether of stearyl alcohol having an average of about 1 to about 21 ethylene oxide 230145 units, the polyethylene glycol ether of cetyl alcohol having an average of about 1 to about 5 ethylene oxide units, and mixtures thereof.
- Additional example of rheology modifiers include thickener or gelling agents, including substances which can increase the viscosity of a composition. Thickening agents include those that can increase the viscosity of a composition without substantially modifying the efficacy of the active ingredient within the formulation.
- Thickening agents can also increase the stability of the formulations of the present application.
- thickening agents include hydrogenated polyisobutene or trihydroxy stearin, or a mixture of both. Additional non-limiting examples of additional thickening agents that can be used in the context of the present application include carboxylic acid polymers, crosslinked polyacrylate polymers, polyacrylamide polymers, polysaccharides, and gums.
- carboxylic acid polymers include crosslinked compounds containing one or more monomers derived from acrylic acid, substituted acrylic acids, and salts and esters of these acrylic acids and the substituted acrylic acids, wherein the crosslinking agent contains two or more carbon-carbon double bonds and is derived from a polyhydric alcohol (see CTFA International Cosmetic Ingredient Dictionary, Fourth Edition, 1991, pp. 12 and 80).
- Examples of commercially available carboxylic acid polymers include carbomers, which are homopolymers of acrylic acid crosslinked with allyl ethers of sucrose or pentaerythritol (e.g., CarbopolTM 900 series from B. F. Goodrich).
- Non-limiting examples of crosslinked polyacrylate polymers include cationic and non-ionic polymers.
- Non-limiting examples of polyacrylamide polymers include polyacrylamide, isoparaffin and Laureth-7, multi-block copolymers of acrylamides and substituted acrylamides with acrylic acids and substituted acrylic acids.
- Non-limiting examples of polysaccharides include cellulose, carboxymethyl hydroxyethylcellulose, cellulose acetate propionate carboxylate, hydroxyethylcellulose, hydroxyethyl ethylcellulose, hydroxypropyl cellulose, hydroxypropyl methylcellulose, methyl hydroxyethylcellulose, microcrystalline cellulose, sodium cellulose sulfate, and 230145 mixtures thereof.
- alkyl substituted cellulose where the hydroxy groups of the cellulose polymer are hydroxyalkylated (preferably hydroxy ethylated or hydroxypropylated) to form a hydroxyalkylated cellulose which is then further modified with a C10-C30 straight chain or branched chain alkyl group through an ether linkage.
- these polymers are ethers of C10-C30 straight or branched chain alcohols with hydroxyalkylcelluloses.
- Other useful polysaccharides include scleroglucans comprising a linear chain of (1-3) linked glucose units with a (1-6) linked glucose every three unit.
- Non-limiting examples of gums that can be used with the present compositions include acacia, agar, algin, alginic acid, ammonium alginate, amylopectin, calcium alginate, calcium carrageenan, carnitine, carrageenan, dextrin, gelatin, gellan gum, guar gum, guar hydroxypropyltrimonium chloride, hectorite, hyaluroinic acid, hydrated silica, hydroxypropyl chitosan, hydroxypropyl guar, karaya gum, kelp, locust bean gum, natto gum, potassium alginate, potassium carrageenan, propylene glycol alginate, sclerotium gum, sodium carboxymethyl dextran, sodium carrageenan, tragacanth gum, xanthan gum, and mixtures thereof.
- the thickening agent is Chondrus crispus (carrageenan) extract.
- Film formers The sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention may advantageously include one or more film formers or film forming agent.
- a film forming agent is a hydrophobic material that imparts water resistance and film forming characteristics to the sunscreen products, cosmetic or pharmaceutical preparations or homecare products.
- Standard film formers are preferably chitosan, microcrystalline chitosan, quaternized chitosan, polyvinyl pyrrolidone, vinyl pyrrolidone/vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid and salts thereof and similar compounds.
- Preferred film formers for improving water resistance of the composition are selected from the group consisting of Polyamide-8 (such as Oleocraft LP 20 PA (MV)), Polyamide-3 (such as Oleocraft MP 32 PA (MV)), Trimethylpentanediol/Adipic Acid/Glycerin Crosspolymer (such as WetFilm), Octyldodecyl Citrate Crosspolymer (such as CosmoSurf CE 100), Polyglyceryl-3 Methyl Glucose Distearate (such as TegoCare 450), C28-52 Olefin/Undecylenic Acid Copolymer 230145 (such as Performa V6112), Hydrolyzed Jojoba esters, Jojoba Esters, Aqua (such as Floraester Jojoba K100), Cyclopentasiloxane Acrylates/Dimethicone copolymer (such as KP545), Acrylates/Beheneth-25 Methacylate Copolymer (such
- the aforesaid film forming agents are used in the sunscreen, cosmetic or pharmaceutical preparation or homecare product either as a single component or preferably in a mixture with two or more further of said film forming agents as specified above.
- the film forming agents are used in amounts effective to allow the final formulation to remain on the skin or surface after exposure to circulating water for at least 40 minutes, preferably 80 minutes.
- the film forming agent is present in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product in an amount of 0.01 to 10.0 % by weight, preferably 0.05 to 8.0 % by weight, based on the total weight of the final formulation.
- Water resistance improving agents The sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention may advantageously include one or more agents for improving water resistance.
- An agent for improving water resistance is a hydrophobic material that imparts film forming and water resistance characteristics to an emulsion.
- suitable water resistance improving agents include copolymers derived from polymerization of octadecene-1 and maleic anhydride.
- a preferred water resistance improving agent is a polyanhydride resin.
- Another preferred water resistance improving agent is a copolymer of vinyl pyrrolidone and eicosene monomers.
- the water resistance improving agent(s) is/are used in amounts effective to allow the final formulation to remain on the skin or surface after exposure to circulating water for at least 40 minutes, preferably 80 minutes.
- One or more water resistance improving agents can optionally be included in the final formulation in an amount ranging from 0.01 to 10.0 % by weight, preferably 0.05 to 8.0 % by weight, more preferably 0.1 to 5.0 % by weight, based on the total weight of the final formulation.
- Silicones In order to impart a silky, spreadable, and luxurious texture and to make skin look and feel smoother, and additionally to improve processability (antifoaming) the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention preferably includes one or more silicones or silicone derivatives. The total amount of silicone compound(s) in the compositions according to the present invention can vary but is typically 0.1 to 35.0 % by weight, based on the total weight of the composition.
- Dry-feel modifiers The sunscreen product or cosmetic or pharmaceutical preparation according to the present invention is preferably combined with dry-feel modifiers.
- a dry-feel modifier is an agent which, when incorporated in an emulsion, imparts a "dry feel" to the skin when the emulsion dries. Dry-feel modifiers may also reduce sunscreen migration on the skin.
- Dry feel modifiers can include starches, talc, kaolin, chalk, zinc oxide, Hydroxyapatite (such as Tinomax CC), silicone fluids, inorganic salts such as barium sulfate and sodium chloride, C6 to C12 alcohols such as octanol; sulfonated oils; surface treated silica, precipitated silica, fumed silica such as Aerosil® available from the Degussa Inc. of New York, N.Y. U.S.A. or mixtures thereof; dimethicone, a mixture of mixture of methylated linear siloxane polymers, available as DC200 fluid, tradename of Dow Corning, Midland, Mich. U.S.A.
- the sunscreen product or cosmetic or pharmaceutical preparation according to the present invention can also contain advantageously one or more lenitive substances, wherein any lenitive substances can be used which are suitable or customary in cosmetic or pharmaceutical applications such as alpha-bisabolol, azulene, guaiazulene, 18-beta-glycyrrhetinic acid, allantoin, Aloe vera juice or gel, extracts of Hamamelis virginiana (witch hazel), Echinacea species, Centella asiatica, chamomile, Arnica montana, Glycyrrhiza species, algae, seaweed and Calendula officinalis, and vegetable oils such as sweet almond oil, baobab oil, olive oil and panthenol, Laureth-9, Trideceth-9 and 4-t
- Physiological cooling agents The sunscreen product or cosmetic or pharmaceutical preparation according to the present invention can be particularly advantageously combined with one or more physiological cooling agent(s).
- the use of cooling agents can alleviate itching.
- Preferred individual cooling agents for use within the framework of the present invention are listed below.
- cooling agents listed can also be used in combination with one another: which are preferably selected here from the following list: menthol and menthol derivatives (for example L-menthol, D-menthol, racemic menthol, isomenthol, neoisomenthol, neomenthol) menthylethers (for example (I-menthoxy)-1,2- propanediol, (l-menthoxy)-2-methyl-1,2-propanediol, l-menthyl-methylether), menthone glyceryl acetal, menthone glyceryl ketal or mixtures of both, menthylesters (for example menthylformiate, menthylacetate, menthylisobutyrate, menthyhydroxyisobutyrat, menthyllactates, L-menthyl-L-lactate, L-menthyl-D-lactate, menthyl-(
- Cooling agents which are preferred due to their particular synergistic effect are l-menthol, d-menthol, racemic menthol, menthone glycerol acetal (trade name: Frescolat ® MGA), menthyl lactate (preferably l-menthyl lactate, in particular l-menthyl l-lactate (trade name: Frescolat ® ML)), substituted menthyl-3-carboxamides (such as menthyl-3-carboxylic acid N-ethyl amide), 2-isopropyl-N-2,3-trimethyl butanamide, substituted cyclohexane carboxamides, 3-menthoxypropane-1,2-diol, 2- hydroxyethyl menthyl carbonate, 2-hydroxypropyl menthyl carbonate and isopulegol.
- menthone glycerol acetal trade name: Frescolat ® MGA
- menthyl lactate preferably l
- cooling agents are l-menthol, racemic menthol, menthone glycerol acetal (trade name: Frescolat ® MGA), menthyl lactate (preferably l-menthyl lactate, in particular l-menthyl l-lactate (trade name: Frescolat ® ML)), 3-menthoxypropane-1,2-diol, 2-hydroxyethyl menthyl carbonate and 2-hydroxypropyl menthyl carbonate.
- menthone glycerol acetal trade name: Frescolat ® MGA
- menthyl lactate preferably l-menthyl lactate, in particular l-menthyl l-lactate (trade name: Frescolat ® ML)
- 3-menthoxypropane-1,2-diol 2-hydroxyethyl menthyl carbonate and 2-hydroxypropyl menthyl carbonate.
- Very particularly preferred cooling agents are l-menthol, menthone glycerol acetal (trade name: Frescolat ® MGA) and menthyl lactate (preferably l-menthyl lactate, in particular l-menthyl l-lactate (trade name: Frescolat ® ML).
- Alkanediols In a further preferred variant, the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the invention comprises one or more linear alkanediol(s) having a carbon chain of 5 to 12 carbon atoms.
- said one or more linear alkanediol(s) is/are selected from the group consisting of 1,2-alkanediols, 2,3-alkanediols, 3,4-alkanediols and 1,3-alkanediols, more preferably of 2,3-alkanediols and 1,3-alkanediols.
- said linear alkanediol(s) is/are selected from the group consisting of 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2-octanediol, 1,2-nonanediol, 1,2-decanediol, 1,2-undecanediol, 1,2-dodecanediol, 2,3- pentanediol, 2,3-hexanediol, 2,3-heptanediol, 2,3-octanediol, 2,3-nonanediol, 2,3- decanediol, 2,3-undecanediol and 2,3-dodecanediol.
- compositions according to the invention comprising one or more linear alkanediol(s) having a carbon chain of 5 to 12 carbon atoms, preferably as defined herein, display particularly advantageous emulsifying properties.
- the one or more of said linear alkanediol(s) (if not emulsions themselves) support(s) the formation of water or oil droplets with a particularly small average size in emulsions or (if emulsions themselves) contain water or oil droplets with a particularly small average size.
- an alkanediol in particular a 1,2- alkanediol or 2,3-alkanediol, improves the solubility of oil components, such as one or more oil body/bodies or wax(es) in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention.
- the oil body/bodies or wax(es) are selected from the group consisting of natural fats and oils, fatty alcohols and alcohols, glyceryl esters and derivatives thereof, esters, ethers, siloxanes and silanes, waxes, and naphthenic hydrocarbons, preferably selected from the group consisting of squalene, dialkylcyclohexanes, tetradecane, isohexadecane, dodecane, docosane, paraffin, and mineral oils, and further described below.
- the composition comprises from 0.01 to 10 % by weight, more preferably from 0.1 to 5 % by weight, still more preferably from 0.3 to 3 % by weight, most preferably from 0.5 to 1 % by weight, of said linear alkanediol(s) having a carbon chain of 5 to 12 carbon atoms and defined herein, based on the total weight of the composition.
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention comprises advantageously one or more antioxidants.
- Suitable antioxidants encompass amino acids (preferably glycine, histidine, tyrosine, tryptophan) and derivatives thereof, imidazoles (preferably urocanic acid) and derivatives thereof, peptides, preferably D,L-carnosine, D-carnosine, L- carnosine and derivatives thereof (preferably anserine), carnitine, creatine, matrikine peptides (preferably lysyl-threonyl-threonyl-lysyl-serine) and palmitoylated pentapeptides, carotenoids, carotenes (preferably alpha-carotene, beta-carotene, lycopene) and derivatives thereof, lipoic acid and derivatives thereof (preferably dihydrolipoic acid), aurothioglucose, propyl thiouracil and other
- chelators preferably alpha-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin, alpha-hydroxy acids (preferably citric acid, lactic acid, malic acid), humic acid, bile acid, bile extracts, tannins, bilirubin, biliverdin, EDTA, EGTA and derivatives thereof), unsaturated fatty acids and derivatives thereof (preferably gamma-linolenic acid, linoleic acid, oleic acid), folic acid and derivatives thereof, ubiquinone and derivatives thereof, ubiquinol and derivatives thereof, vitamin C and derivatives (preferably ascorbyl palmitate, Mg ascorbyl phosphate, ascorbyl acetate, ascorbyl glucoside), tocopherols and derivatives (preferably vitamin E acetate), vitamin A and derivatives (vitamin A palmitate) and coniferyl benzoate of benzoic resin,
- metal chelators preferably alpha-hydroxy fatty
- Emulsifiers include amphoteric, anionic, cationic or nonionic emulsifiers, used alone or as a mixture.
- the emulsifiers are chosen in an appropriate manner according to the emulsion to be obtained.
- Preferred examples include: - products of the addition of 2 to 30 mol ethylene oxide and/or 0 to 5 mol propylene oxide onto linear C8-22 fatty alcohols, onto C12-22 fatty acids and onto alkyl phenols containing 8 to 15 carbon atoms in the alkyl group; - C12/18 fatty acid monoesters and diesters of addition products of 1 to 30 mol ethylene oxide onto glycerol; - glycerol mono- and diesters and sorbitan mono- and diesters of saturated and 230145 unsaturated fatty acids containing 6 to 22 carbon atoms and ethylene oxide addition products thereof; - addition products of 15 to 60 mol ethylene oxide onto castor oil and/or hydrogenated castor oil; - polyol esters and, in particular, polyglycerol esters such as, for example, polyglycerol polyricinoleate, polyglyce
- Mixtures of compounds from several of these classes are also suitable; - addition products of 2 to 15 mol ethylene oxide onto castor oil and/or hydrogenated castor oil; - partial esters based on linear, branched, unsaturated or saturated C6/22 fatty acids, ricinoleic acid and 12-hydroxystearic acid and glycerol, polyglycerol, pentaerythritol, dipentaerythritol, sugar alcohols (for example sorbitol), alkyl glucosides (for example methyl glucoside, butyl glucoside, lauryl glucoside) and polyglucosides (for example cellulose); - mono-, di and trialkyl phosphates and mono-, di- and/or tri-PEG-alkyl phosphates and salts thereof; - wool wax alcohols; - polysiloxane/polyalkyl polyether copolymers and corresponding derivatives; - mixed esters of pentaery
- the addition products of ethylene oxide and/or propylene oxide onto fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters and sorbitan mono- and diesters of fatty acids or onto castor oil are known commercially available products. They are homologue mixtures of which the average degree of alkoxylation corresponds to the ratio between the quantities of ethylene oxide and/or propylene oxide and substrate with which the addition reaction is carried out. C12/18 fatty acid monoesters and diesters of 230145 addition products of ethylene oxide onto glycerol are known as lipid layer enhancers for cosmetic formulations.
- Partial glycerides Typical examples of suitable partial glycerides are hydroxystearic acid monoglyceride, hydroxystearic acid diglyceride, isostearic acid monoglyceride, isostearic acid diglyceride, oleic acid monoglyceride, oleic acid diglyceride, ricinoleic acid monoglyceride, ricinoleic acid diglyceride, linoleic acid monoglyceride, linoleic acid diglyceride, linolenic acid monoglyceride, linolenic acid diglyceride, erucic acid monoglyceride, erucic acid diglyceride, tartaric acid monoglyceride, tartaric acid diglyceride, citric acid monoglyceride, citric acid diglyceride, malic acid monoglyceride, malic acid diglyceride, malic acid monoglyceride, malic acid diglyceride, malic
- Sorbitan esters are sorbitan monoisostearate, sorbitan sesquiisostearate, sorbitan diisostearate, sorbitan triisostearate, sorbitan monooleate, sorbitan sesquioleate, sorbitan dioleate, sorbitan trioleate, sorbitan monoerucate, sorbitan sesquierucate, sorbitan dierucate, sorbitan trierucate, sorbitan monoricinoleate, sorbitan sesquiricinoleate, sorbitan diricinoleate, sorbitan triricinoleate, sorbitan monohydroxystearate, sorbitan sesquihydroxystearate, sorbitan dihydroxystearate, sorbitan trihydroxystearate, sorbitan monotart
- Polyglycerol esters Typical examples of suitable polyglycerol esters are Polyglyceryl-2 Dipolyhydroxystearate (Dehymuls ® PGPH), Polyglycerin-3-Diisostearate (Lameform ® TGI), Polyglyceryl-4 Isostearate (Isolan ® GI 34), Polyglyceryl-3 Oleate, Diisostearoyl Polyglyceryl-3 Diisostearate (Isolan® PDI), Polyglyceryl-3 Methylglucose 230145 Distearate (Tego Care ® 450), Polyglyceryl-3 Beeswax (Cera Bellina ® ), Polyglyceryl-4 Caprate (Polyglycerol Caprate T2010/90), Polyglyceryl-3 Cetyl Ether (Chimexane ® NL
- polystyrene resin examples include the mono-, di- and triesters of trimethylol propane or pentaerythritol with lauric acid, cocofatty acid, tallow fatty acid, palmitic acid, stearic acid, oleic acid, behenic acid and the like optionally reacted with 1 to 30 mol ethylene oxide.
- Anionic emulsifiers are aliphatic C12 to C 22 fatty acids, such as palmitic acid, stearic acid or behenic acid for example, and C12 to C22 dicarboxylic acids, such as azelaic acid or sebacic acid for example, potassium cetyl phosphate, and hydrogenated palm glycerides (Emulsiphos/Emulsiphos F).
- Amphoteric emulsifiers Other suitable emulsifiers are amphoteric or zwitterionic surfactants.
- Zwitterionic surfactants are surface-active compounds which contain at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule.
- Particularly suitable zwitterionic surfactants are the so-called betaines, such as the N-alkyl-N,N-dimethyl ammonium glycinates, for example cocoalkyl dimethyl ammonium glycinate, N-acylaminopropyl-N,N-dimethyl ammonium glycinates, for example cocoacylaminopropyl dimethyl ammonium glycinate, and 2-alkyl-3- carboxymethyl-3-hydroxyethyl imidazolines containing 8 to 18 carbon atoms in the alkyl or acyl group and cocoacylaminoethyl hydroxyethyl carboxymethyl glycinate.
- Ampholytic surfactants are also suitable emulsifiers.
- Ampholytic surfactants are surface-active compounds which, in addition to a C8/18 alkyl or acyl group, contain at least one free amino group and at least one ⁇ COOH- or -SO3H- group in the molecule and which are capable of forming inner salts.
- ampholytic surfactants are N-alkyl glycines, N-alkyl propionic acids, N-alkylaminobutyric acids, N- alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropyl glycines, N-alkyl taurines, N-alkyl sarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids containing around 8 to 18 carbon atoms in the alkyl group.
- Particularly preferred 230145 ampholytic surfactants are N-cocoalkylaminopropionate, cocoacylaminoethyl aminopropionate and C12/18 acyl sarcosine.
- Anti-ageing actives A composition according to the present invention is preferably combined with one or more anti-ageing actives.
- anti-ageing or biogenic agents are, for example antioxidants, matrix-metalloproteinase inhibitors (MMPI), skin moisturizing agents, glycosaminglycan stimulators, anti- inflammatory agents, TRPV1 antagonists and plant extracts.
- MMPI matrix-metalloproteinase inhibitors
- skin moisturizing agents for example antioxidants, matrix-metalloproteinase inhibitors (MMPI), skin moisturizing agents, glycosaminglycan stimulators, anti- inflammatory agents, TRPV1 antagonists and plant extracts.
- Matrix-Metalloproteinase inhibitors are preferably combined with one or more matrix-metalloproteinase inhibitors, especially those inhibiting matrix-metalloproteinases enzymatically cleaving collagen, selected from the group consisting of ursolic acid, retinyl palmitate, propyl gallate, precocenes, 6-hydroxy-7-methoxy-2,2-dimethyl-1(2H)-benzopyran, 3,4-dihydro- 6-hydroxy-7-methoxy-2,2-dimethyl-1(2H)-benzopyran, benzamidine hydrochloride, the cysteine proteinase inhibitors N-ethylmalemide and epsilon-amino-n-caproic acid of the serinprotease inhibitors: phenylmethylsufonylfluoride, collhibin (company Pentapharm; INCI: hydrolysed rice protein), oenotherol (
- the sunscreen product or cosmetic or pharmaceutical preparation according to the present invention comprises advantageously one or more skin-moisturizing and/or moisture-retaining substances.
- Preferred skin moisturizing and/or moisture-retaining substances are selected from the group consisting of alkane diols or alkane triols comprising 3 to 12 carbon atoms, preferably C3-C10-alkane diols and C3-C10-alkane triols. More preferably the skin moisturizing agents are selected from the group consisting of glycerol, 1,2- propylene glycol, 1,2-butylene glycol, 1,3-butylene glycol, 1,2-pentanediol, 1,2- hexanediol, 1,2-heptanediol, 1,2-octanediol, and 1,2-decanediol.
- Further skin moisturizing and/or moisture-retaining substances include sodium lactate, urea, urea derivatives, alcohols, glycerol, diols such as propylene glycol, hexylene glycol, collagen, elastin or hyaluronic acid, diacyl adipates, petrolatum, urocanic acid, lecithin, panthenol, phytantriol, lycopene, (pseudo-)ceramides, glycosphingolipids, cholesterol, phytosterols, chitosan, chondroitin sulfate, lanolin, lanolin esters, amino acids, alpha-hydroxy acids (such as citric acid, lactic acid, malic acid) and their derivatives, mono-, di- and oligosaccharides such as glucose, galactose, fructose, mannose, fructose and lactose, polysugars such as R-glucans, in particular 1,3-1,4
- Glycosaminoglycan stimulators Preferred compositions according to the present invention comprise one or more substances stimulating the synthesis of glycosaminoglycans which are selected from the group consisting of hyaluronic acid and derivatives or salts, Subliskin (Sederma, INCI: Sinorhizobium Meliloti Ferment Filtrate, Cetyl Hydroxyethylcellulose, Lecithin), Hyalufix (BASF, INCI: Water, Butylene Glycol, Alpinia galanga leaf extract, Xanthan Gum, Caprylic/Capric Triglyceride), Stimulhyal (Soliance, INCI: Calcium ketogluconate), Syn-Glycan (DSM, INCI: Tetradecyl Aminobutyroylvalylaminobutyric Urea Trifluoroacetate, Glycerin, Magnesium chloride), Kalpariane (Biotech Marine), DC Upregulex (Distinctive Cosmetic Ingredient
- Dragosantol and Dragosantol 100 from Symrise, oat glucan, Echinacea purpurea extract and soy protein hydrolysate.
- Preferred actives are selected from the group consisting of hyaluronic acid and derivatives or salts, retinol and derivatives, (-)-alpha-bisabolol or synthetic alpha-bisabolol such as e.g.
- Anti-inflammatory agents are preferably combined with anti-inflammatory and/or redness and/or itch ameliorating ingredients, in particular steroidal substances of the corticosteroid type selected from the group consisting of hydrocortisone, dexamethasone, dexamethasone phosphate, methyl prednisolone or cortisone, are advantageously used as anti-inflammatory active ingredients or active ingredients to relieve reddening and itching, the list of which can be extended by the addition of other steroidal anti-inflammatories. Non-steroidal anti- inflammatories can also be used.
- steroidal anti-inflammatory substances of the corticosteroid type in particular hydrocortisone, hydrocortisone derivatives such as hydrocortisone 17-butyrate, dexamethasone, dexamethasone phosphate, methylprednisolone or cortisone
- non-steroidal anti-inflammatory substances in particular oxicams such as piroxicam or tenoxicam, salicylates such as aspirin, disalcid, solprin or fendosal, acetic acid derivatives such as diclofenac, fenclofenac, indomethacin, sulindac, tolmetin or clindanac, fenamates such as mefenamic, meclofenamic, flufenamic or niflumic, propionic acid derivatives such as ibuprofen, naproxen or benoxaprofen, pyrazoles such as phenylbutazone, oxy
- TRPV1 antagonists e.g.4-t-Butylcyclohexanol
- NK1 antagonists e.g. Aprepitant, Hydroxyphenyl Propamidobenzoic Acid
- cannabinoid receptor agonists e.g. Palmitoyl Ethanolamine
- TRPV3 antagonists e.g. Palmitoyl Ethanolamine
- oxicams such as piroxicam or tenoxicam
- salicylates such as aspirin, disalcid, solprin or fendosal
- acetic acid derivatives such as diclofenac, fenclofenac, indomethacin, sulindac, tolmetin or clindanac
- fenamates such as mefenamic, meclofenamic, flufenamic or niflumic
- propionic acid derivatives such as ibuprofen, naproxen, benoxaprofen or pyrazoles such as phenylbutazone, oxyphenylbutazone, febrazone or azapropazone.
- Anthranilic acid derivatives are preferred anti-itch ingredients in a composition according to the present invention.
- Also useful are natural or naturally occurring anti-inflammatory mixtures of substances or mixtures of substances that alleviate reddening and/or itching, in particular extracts or fractions from camomile, Aloe vera, Commiphora species, Rubia species, willow, willow-herb, oats, calendula, arnica, St John’s wort, honeysuckle, rosemary, Passiflora incarnata, witch hazel, ginger or Echinacea; preferably selected from the group consisting of extracts or fractions from camomile, Aloe vera, oats, calendula, arnica, honeysuckle, rosemary, witch hazel, ginger or Echinacea, and/or pure substances, preferably alpha-bisabolol, apigenin, apigenin-7-glucoside, gingerols, shogaols, gingerdiols, dehydr
- TRPV1 antagonists Preferred compositions according to the present invention comprise one or more TRPV1 antagonists. Suitable compounds which reduce the hypersensitivity of skin nerves based on their action as TRPV1 antagonists, encompass e.g., trans-4-tert-butyl cyclohexanol, or indirect modulators of TRPV1 by an activation of the ⁇ -receptor, e.g., acetyl tetrapeptide-15, are preferred.
- Antimicrobial agents The sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention can advantageously combined with an antimicrobial agent which act primarily against microorganisms, in particular bacteria, yeast and/or fungi and includes one or more antimicrobial agents such as Caprylhydroxamic Acid, o-Cymen-5-ol, Isopropylparaben, Capryloyl Glycine, Phenylpropanol, Tropolone, PCA Ethyl Cocoyl Arginate, 2-Methyl 5-Cyclohexylpentanol, Phenoxyethanol, Disodium EDTA, Methylparaben and its salts, Sodium Benzoate, Benzyl Alcohol, Potassium Sorbate, Benzyl Salicylate, Propylparaben, Sodium Methylparaben, Methylchloroisothiazolinone, Methylisothiazolinone, Ethylhe
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention comprises one or more antimicrobial agents selected from the group consisting of 1,2-pentanediol, 1,2-hexanediol, 1,2- heptanediol, 1,2-octanediol, 1,2-nonanediol, 1,2-decanediol, 1,2-undecanediol, 1,2- dodecanediol, 2,3-pentanediol, 2,3-hexanediol, 2,3-heptanediol, 2,3-octanediol, 2,3- nonanediol, 2,3-decanediol, 2,3-undecanediol, 2,3-dodecanediol, 2-benzylheptanol, 2- hydroxyacetophenone, 2-methyl 5-cyclohexylpentan
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention comprises one or more antimicrobial agent selected from the group consisting of 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2- octanediol, 1,2-nonanediol, 1,2-decanediol, 1,2-undecanediol, 1,2-dodecanediol, 1,2- tridecanediol, 4-hydroxyacetophenone, and any mixture thereof.
- one or more antimicrobial agent selected from the group consisting of 1,2-pentanediol, 1,2-hexanediol, 1,2-heptanediol, 1,2- octanediol, 1,2-nonanediol, 1,2-decanediol, 1,2-undecanediol, 1,2-dodecanediol, 1,2- tri
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product as defined herein is advantageously combined with at least one further antimicrobial agent which is different from the antimicrobial agents specified above.
- the combination with a further antimicrobial agent provides reliable protection against microbial degradation and deterioration of the preparation, in particular during storage.
- the further different antimicrobial agent provides reliable protection against other microorganisms as described above, for example Corynebacterium, Anaerococcus, Finegoldia, Moraxella, Porphyromonas, Fusobacterium, Malassezia, Peptoniphilus, Streptococcus, Lactobacillus, Gardnerella, Fannyhessea, Epidermophyton, Trichophyton, Cutibacterium.
- the combination with a further different antimicrobial agent allows antimicrobial protection against different groups of microorganisms, and, thus, a broader spectrum of microorganism.
- the further different antimicrobial agent in the context of the present invention is preferably selected from the group consisting of 2-benzylheptanol, alkyl (C 12-22) trimethyl ammonium bromide and chloride, ascorbic acid and salts thereof, 230145 benzalkonium bromide, benzalkonium chloride, benzalkonium saccharinate, benzethonium chloride, Benzoic Acid, camphor, cetylpyridinium chloride, chlorhexidine diacetate, chlorhexidine dihydrochloride, chlorocresol, chloroxylenol, Cyclohexylglycerin, Dimethyl phenylbutanol, Dimethyl phenylpropanol, ethanol, ethyl lauroyl arginate HCl, Ethyl Lauroyl Arginate Laurate, eucalyptol, gluconic acid and salts thereof, glycerin, hexamidine, hexamidine diise
- the aforesaid antimicrobial agents are used in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product either as a single component or preferably in a mixture with two or more further of said antimicrobial agents as specified above.
- the antimicrobial agent is present in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product in an amount of 0.01 to 25.0 % by weight, preferably 0.02 to 15.0 % by weight, most preferred in an amount of 0.05 to 6.0 % by weight, based on the total weight of the final formulation.
- the at least one antimicrobial alkanediol is present in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product in an amount of 0.1 to 5 % by weight, based on the total weight of the final formulation and/or the 4-hydroxyacetophenone in an amount of 0.01 to 2 % by weight, based on the total weight of the final formulation.
- Preservatives For preservative purposes, the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention 230145 preferably includes one or more preservatives which are suitable or customary in sunscreen products, cosmetic or pharmaceutical preparations or homecare products.
- Suitable and advantageously preservatives are, for example, benzoic acid, sodium benzoate, ammonium benzoate, butyl benzoate, calcium benzoate, ethyl benzoate, isobutyl benzoate, isopropyl benzoate, magnesium benzoate, mea-benzoate, methyl benzoate, phenyl benzoate, potassium benzoate, propyl benzoate, propionic acid, ammonium propionate, calcium propionate, magnesium propionate, potassium propionate, sodium propionate, salicylic acid, calcium salicylate, magnesium salicylate, measalicylate, sodium salicylate, potassium salicylate, teasalicylate, sorbic acid, calcium sorbate, sodium sorbate, potassium sorbate, o-phenylphenol, sodium sulfite, ammonium bisulfite, ammonium sulfite, potassium sulfite, potassium hydrogen sulfite, sodium bisulfite, sodium metabis
- Drugs The sunscreen product or cosmetic or pharmaceutical preparation according to the present invention are preferably combined with one or more drugs.
- the pharmaceutically active agent is selected from anti-acne agents, agents used to treat rosacea, analgesics, anesthetics, anorectals, antihistamines, anti-inflammatory agents including non-steroidal anti-inflammatory drugs, antibiotics, antifungals, antivirals, antimicrobials, anti-cancer actives, scabicides, pediculicides, antineoplastics, antiperspirants, antipruritics, antipsoriatic agents, antiseborrheic agents, biologically active proteins and peptides, burn treatment agents, cauterizing agents, depigmenting agents, depilatories, diaper rash treatment agents, enzymes, hair growth stimulants, hair growth retardants including eflornithine and its salts and analogs, hemostatics, kerotolytics, canker sore treatment agents, cold sore treatment agents
- sunscreen product or cosmetic or pharmaceutical, in particular dermatological, preparation is intended for topical applications.
- topical is understood to mean external applications on a mammal’s skin or mucosa, which are in particular for the protection, treatment, care and cleansing of the skin, scalp, eyelashes, eyebrows, nails, mucous membranes and hair.
- the mammal is preferably a human.
- the cosmetic or pharmaceutical preparation is either a rinse off or a leave on preparation.
- the sunscreen products according to the present invention may be in the form of an aqueous solution, dispersions, a hydro alcoholic vehicle, a stick, an ointment, a gel, an aerosol (foams, sprays, propellant pump) and the like.
- the sunscreen product, cosmetic or pharmaceutical, in particular dermatological, preparation or homecare product according to the first aspect of the present invention can be present in different forms, e.g.
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the first aspect of the invention is a dispersion.
- the term “dispersion” in the context of the present invention means, that the sunscreen product, cosmetic or pharmaceutical preparation or homecare product is a disperse two-phase system consisting of colloidal particles (disperse phase) and a medium in which they are suspended (disperse medium).
- Such dispersions for example emulsions, comprise the at least one oil component (without UV-filters) preferably in an amount of ⁇ 1 % by weight, more preferably in an amount of ⁇ 3 % by weight.
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the first aspect of the present invention takes various forms such as an emulsion, in particular a O/W emulsion, a W/O emulsion, a multiple emulsion, a hydrodispersion gel, a balm, a multiple emulsion of the water-in-oil type (W/O/WO) or of the oil-in-water type (O/W/O), PIT emulsion, Pickering emulsion, a micro- emulsion, a liquid, a lotion, a suspension, a milk, an ointment, a paste, a gel, a cream based, an oil based or a liposome-based formulation or a an aerosol such as foams and sprays, including all types of silicon based emulsions.
- an emulsion in particular a O/W emulsion, a W/O emulsion, a multiple emulsion, a
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention is in the form of an emulsion as defined herein, advantageously in the form of an oil-in-water (O/W) emulsion comprising an oily phase dispersed in an aqueous phase in the presence of an O/W or polymeric emulsifier.
- O/W oil-in-water
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention is a dispersion, preferably an emulsion
- the oil component is present in the cosmetic or pharmaceutical preparation in an amount of 0.01 to 50.0 % by weight, based on the total weight of the composition.
- the cosmetic or pharmaceutical preparation comprises the oil component in an amount of 0.1 to 45.0 % by weight, based on the total weight of the composition.
- the oil component is advantageously used in the cosmetic or pharmaceutical preparation in an amount of at 1.0 to 40 % by weight, based on the total weight of the composition.
- the sunscreen product, cosmetic or pharmaceutical, preferably dermatological, preparation or homecare product according to the first of the invention is a water free formulation, i.e. an oil formulation.
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention is a water free formulation, i.e.
- oil component is present in the cosmetic or pharmaceutical preparation in an amount of ⁇ 60 % by weight, preferably in an amount of ⁇ 75 % by weight, more preferably in an amount of ⁇ 90 % by weight, based on the total weight of the composition.
- water free formulations include e.g. oils, skin butters, powders, lip stick, antiperspirant/deo sticks, and decorative cosmetics.
- further water free formulations are likewise formulations on the basis of ethanol/diols/triols/glycols such as sprays or gels.
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product as disclosed herein is an aqueous or an aqueous/alcoholic, preferably aqueous/ethanolic, an aqueous/glycolic, or an alcoholic/glycolic, preferably ethanolic/glycolic, based solution.
- this could be glycerin in water or alcohol compositions.
- Said solutions are homogeneous one phase system of water/alcohol/glycol and additional components.
- the aqueous/alcoholic or aqueous/glycolic or alcoholic/glycolic based solution comprises an aliphatic alcohol or a glycol in an amount of 0.1 to 70.0 % by weight, preferably in an amount of 0.5 to 60.0 % by weight, more preferably in an amount of 1.0 to 50.0 % by weight, based on the total weight of the solution.
- the aliphatic alcohol is preferably selected from the group consisting of ethanol, 230145 isopropanol, n-propanol.
- the glycol is preferably selected from the group consisting of glycerin, propylene glycol, 1,3-Propanediol, 1,2-Propanediol, 1,2–C5 to C10-alkanediols, butylene glycol or dipropylene glycol.
- the overall water content in the final aqueous based solutions can be ⁇ 30 % by weight, more preferably ⁇ 40 % by weight, most preferably ⁇ 50 % by weight.
- Such aqueous or aqueous/alcoholic or aqueous/glycolic or alcoholic/glycolic based solutions include for example deo/antiperspirant preparations, after shave, cleansing preparations, or anti-acne preparations.
- the inventive composition is an impregnation solution in the form of an emulsion spray or ethanol/oil spray for wet wipes.
- the cosmetic preparation is a preparation for cosmetic and/or non-therapeutic use for personal care, skin protection, skin care, scalp protection, scalp care, hair care, nail care, in particular for the prevention and treatment of skin conditions, intolerant or sensitive skin, skin irritation, skin reddening, wheals, pruritis (itching), skin aging, wrinkle formation, loss of skin volume, loss of skin elasticity, piment spots, pigment abnormalities, skin dryness, flaking, greasiness, hypopigmentation and/or hyperpigmentation of the skin; or a preparation for animal care.
- Examples of personal care are preferably anti-ageing preparations, skin care emulsions, body oils, body lotions, cleansing lotions, face or body balms, after shave balms, after sun balms, deo emulsions, cationic emulsions, body gels, treatment creams, skin protection ointments, moisturizing gels, face and/or body moisturizers, light protective preparations (sunscreens), micellar water, hair sprays, color protection hair care products, skin lightning products, anti-dark-spot reparation, etc.
- the cosmetic preparations include also make-ups, eye-care preparation, eye shadows, mascara, eyeliner, lip care preparation such as lip stick, lip gloss, mail care preparations, such as nail varnish, nail varnish removers, [0444]
- the preparation according to the present invention is a preparation of medical use.
- the pharmaceutical, in particular dermatological, composition according to the present invention is preferably a preparation for the prevention and treatment of a condition of the skin, mucosa, nails or hair.
- the sunscreen product or cosmetic or pharmaceutical, in particular dermatological composition according to the first aspect of the present invention is applied to the skin, hair, scalp and/or nails in an adequate amount in such manner as is customary with sunscreen products or cosmetics and dermatological products.
- the products and preparations according to the present invention are homecare products.
- the home care products generally include laundry detergents (powder, liquid and tablet), fabric conditioners, dishwashing detergents (liquid and tablet), hard floor and surface cleaners, glass cleaners, carpet cleaners, oven cleaners, air fresheners, disinfectants, stain removers, car wash products. These products are usually manufactured in the form of a liquid, powder, spray, granules and others.
- a mycosporine-like amino acid compound or its salt as defined in the present application have the effect of improving SPF and boosting the UVA photoprotection of a formulation comprising an inorganic UV- filter.
- the critical wavelength of a sunscreen product, cosmetic or pharmaceutical 230145 preparation or homecare product comprising an inorganic UV-filter can be increased to provide a broad-spectrum coverage having a critical wavelength greater than 370 nm.
- the mycosporine-like amino acid compounds are particularly effective in improving the SPF and/or UVA photoprotection of a sunscreen product, cosmetic or pharmaceutical preparation or homecare product when they are in the form of an acid or in salt form as described above in detail.
- the SPF of a sunscreen product or a cosmetic or pharmaceutical preparation comprising 230145 an inorganic UV-filter can be increased by at least 10 %, preferably by at least 30 %, and more preferred by at least 50 % as it is demonstrated in the following examples.
- the addition of MAA-13 in an amount of 1.0 % results in an in vitro SPF of 45.2 which is 45.8 % higher than the in vitro SPF of the reference sample, i.e. the sample without the addition of the mycosporine-like amino acid compound.
- the addition of MAA-13 in an amount of 3.0 % by weight even results in an in vitro SPF of 44.0 which is 41.9 % higher compared to the in vitro SPF of the reference sample, i.e. the sample without the addition of the mycosporine-like amino acid compound.
- UVA-PF UVA photoprotection
- the addition of MAA-13 also increases the broad-spectrum protection from a critical wavelength of 374 nm to critical wavelengths of 378 nm and 379 nm depending on the concentration of the MAA-13. Hence, the addition of MAA-13 leads to an improvement of the SPF as well as of the UVA-PF in a sunscreen product, cosmetic or 230145 pharmaceutical preparation or homecare product comprising an inorganic UV-filter in the form of an oil-in-water emulsion.
- the addition of MAA-13 in an amount of 1.0 % results in an in vitro SPF of 25.1 which is 14 % higher than the in vitro SPF of the reference sample, i.e. the sample without the addition of the mycosporine-like amino acid compound.
- the addition of a certain mycosporine- like amino acid compound in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprising an inorganic UV-filter results also in a UVA- PF boosting.
- the addition of MAA-1 in an amount of 1.0 % result in an improvement of the UVA-PF of 5.7 % compared to the control sample, i.e. containing none mycosporine- like amino acid compound.
- the addition of MAA-1 in an amount of 3.0 % results even in an improvement of the UVA-PF of 15.2 % compared to the control sample, i.e. containing none mycosporine-like amino acid compound, compared to the control sample, i.e.
- the addition of MAA-13 in an amount of 1.0 % result in an improvement of the UVA-PF of 6.5 % compared to the control sample, i.e. containing none mycosporine-like amino acid compound.
- the addition of MAA-13 in an amount of 3.0 % results even in an improvement of the UVA-PF of 30.6 % compared to the control sample, i.e. containing none mycosporine-like amino acid compound. compared to the control sample, i.e. containing none mycosporine-like amino acid compound.
- the addition of MAA-1 and MAA-13 also increases the broad-spectrum protection from a critical wavelength of 373 nm to critical wavelengths of 379 nm and 380 nm depending on the concentration of the MAA-13.
- the addition of MAA-20 in an amount of 1.0 % by weight results in an in vitro SPF of 51.0 which is 19.2 % higher than the in vitro SPF of the reference sample, i.e. the control example without the addition of the mycosporine-like amino acid compound, in an O/W sunscreen formulation comprising ZnO.
- the addition of MAA-20 in an amount of 1.0 % results in an improvement of the UVA-PF of 0.16 compared to the control sample, i.e. containing none mycosporine-like amino acid compound.
- the addition of MAA-20 also increases the broad-spectrum protection from a critical wavelength of 373 nm to 374 nm.
- the addition of MAA-20 leads to an improvement of the SPF as well as of the UVA-PF in a sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprising an inorganic UV-filter in the form of an oil-in-water emulsion.
- MAA-20 The addition of MAA-20 to a W/O ZnO sunscreen formulation also results in an increase SPF, compared to the W/O ZnO sunscreen formulation without MAA-20, as it is demonstrated by the following examples.
- Similar SPF and/or UVA photoprotection improving effects can be shown for the mycosporine-like amino acid compounds MAA-2, MAA-3, MAA-4, MAA-5, MAA-6, MAA- 7, MAA-8, MAA-9, MAA-11, MAA-12, MAA-13, MAA-14, MAA-16, MAA-17, and MAA-20 to MAA-39.
- Said compounds show an increase in SPF by at least 10 % and an increase in UVA-PF of at least 5 % relative to an otherwise identical sunscreen product, cosmetic or pharmaceutical preparation or homecare product without the mycosporine-like amino acid compound (b). 230145 [0468] Hence, the addition of a mycosporine-like amino acid compound leads to an improvement of the SPF as well as of the UVA photoprotection (UVA-PF) in a sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprising an inorganic UV-filter.
- UVA-PF UVA photoprotection
- UVA-PF UVA photoprotection
- the present invention provides for a sunscreen product, cosmetic or pharmaceutical preparation or homecare product wherein the SPF is increased by at least 10 % compared to a sunscreen product, cosmetic or pharmaceutical preparation or homecare product without the mycosporine-like amino acid compound (b), preferred by at least 15 %, and more preferred by at least 20 %.
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention provides an increase in UVA photoprotection (UVA-PF) of at least 5 % relative to an otherwise identical formulation without the mycosporine-like amino acid compound (b).
- the sunscreen product, cosmetic or pharmaceutical preparation or homecare product provides an increase in UVA-PF of at least 10 %, more preferred by at least 15 %, relative to an otherwise identical formulation without the mycosporine-like amino acid compound.
- the improved/enhanced UV-filter performance allows to reduce the amount of inorganic UV-filter without affecting the envisaged sun protection factor (SPF).
- the present invention relates in a further aspect to the use of a mycosporine-like amino acid compound as defined herein or a mixture thereof for improving the SPF, the UVA photoprotection (UVA-PF) as well as the increase in the critical wavelength of a sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprising at least one inorganic UV-filter.
- a mycosporine-like amino acid compound as defined herein or a mixture thereof for improving the SPF, the UVA photoprotection (UVA-PF) as well as the increase in the critical wavelength of a sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprising at least one inorganic UV-filter.
- the SPF of a sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprising an inorganic UV-filter can be boosted by at least 10 % relative to a sunscreen product, cosmetic or pharmaceutical preparation or homecare product without the mycosporine-like amino acid compound (b), preferred by at least 15 %, and more preferred even by at least 20 %.
- the UVA photoprotection (UVA-PF) in a sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprising an inorganic UV-filter can be boosted by at least 5 %, preferred by at least 10 %, and most preferred by at least 15 %, relative to an otherwise identical formulation without the mycosporine-like amino acid compound.
- the present invention relates to a method of enhancing or boosting the SPF performance and the UVA photoprotection of a sunscreen product, cosmetic or pharmaceutical preparation or homecare product. In the method an effective amount of at least one mycosporine-like amino acid as defined herein or a mixture thereof is added to said sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprising an inorganic UV-filter.
- the present invention relates in a further aspect to a method of providing anti-aging benefits to skin, whitening or preventing darkening of skin, improving the appearance of skin, diminishing the visible signs of skin aging and improving skin’s radiance and firmness by topically applying the sunscreen product, cosmetic or pharmaceutical preparation or homecare product according to the present invention.
- 230145 [0477] The present invention shall now be described in detail with reference to the following examples, which are merely illustrative of the present invention, such that the content of the present invention is not limited by or to the following examples.
- Example 1 Determination of the in-vitro SPFs
- the SPF boosting and UVA-PF boosting test is carried out as in-vitro determination of SPFs.
- Principle The formulation to be tested (emulsion, solution) is weighed on PMMA plates with the help of an analytical balance. The formulation if distributed and incorporated on the plate using a method corresponding to the formulation. The thus prepared plates are then measured on a Labsphere device and the results are calculated as SPF with a suitable software. [0481] 1.
- Sample preparation [0482] PMMA plates (Polymethylmethacrylate), measuring 3 cm x 8.5 cm (WW5 plates based on ISOethA 24443:2012 “Determination of UVA photoprotection in vitro” with 5 ⁇ roughness by Schönberg GmbH & Co. AG) are used to perform an SPF measurement. [0483] 1.1 Preparation of reference samples: [0484] A reference sample is obtained by distributing 25 to 28 mg glycerin (99.5 %) with the index finger on the roughened side of the PMMA plate. The glycerin film must be very thin and uniform. Subsequently, this plate is stored for at least 2 hours.
- the reference plate is measured with the following transmission values: 290 nm > 60 % transmission; 300 nm > 69 % transmission; and 320 nm > 82 % transmission. 230145 [0486]
- Phase 2 The sample is massaged into the rough surface with strong pressure and the process should last 30 seconds. In this context under strong pressure means that when massaged on a scale, this indicates at least 200 m.
- Sun oils The product quantity is generally 1.3 mg/cm2. For strongly spreading oils, less product is applied, as the amount of oil cannot be "absorbed” from the plate. Then the amount of application should be reduced to 1.0-0.75 mg/cm2. Application method here is also the 30 s fast/light and 30 s strong method”.
- Sun sprays The "30/30 method” applies here (especially for thicker sprays). For very liquid sprays (similar to water): Fast and uniform distribution with a slight pressure, until the emulsion "breaks". The process should take 45 s.
- the irradiance set on the external device is 765 W/m2 as standard. The complete naming of the sample is done via Study", "Study Information”. [0495] 2.2 Sample measurement: [0496] At the beginning of the measurement, a blank value of the glycerin reference sample is measured ("scan blank plate”). In order to determine the SPF of a sample, a total of 15 measuring points (3 plates of 5 measuring points) are then created ("Scan Location"). The already scanned plates and measuring points are checked in the upper right window, while the absorbance of the currently measured plate is displayed in the middle window.
- the device calculates an irradiation dose (Irradiation Dose/J/cm2) and the duration (exposure time) for each plate.
- irradiation duration average value of the 3 plates.
- Example 1.1 - O/W ZnO emulsion [0503]
- the formulation samples A to E as specified in the following Table 4 and the formulation samples A and B as specified in the following Table 5 were prepared as follows: [0504] Phase A: The ingredients of phase A were heated to 85 °C in order to dissolve the ingredients. [0505] Phase A: The pigments were dissolved in the ingredients of phase B while stirring and homogenized (Ultra Turrax® T25: 10,000 rpm/10 min). At the end of the homogenization the Keltrol® is added and dispersed. 230145 [0506] Phase B: The ingredients of phase B were mixed and dissolved while stirring. The water phase will be cloudy in combination with the sodium hydroxide solution.
- the in vitro SPF is highly improved, i.e. increased by the combination of the formulation with a certain mycosporine-like amino acid compound.
- the control example containing no mycosporine-like amino acid compound exhibited an SPF of 31.0.
- the addition of MAA-1 in an amount of 1.0 % by weight however results in an in vitro SPF of 44.0 which is 42 % higher than the in vitro SPF of the reference sample, i.e. the sample without the addition of the mycosporine-like amino acid compound.
- the sample without the addition of the mycosporine-like amino acid compound without the addition of the mycosporine-like amino acid compound.
- an improved SPF results from the addition of a certain mycosporine-like amino acid compound in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprising an inorganic UV-filter, but also a boosted UVA-PF.
- the addition of MAA-13 in an amount of 1.0 % result in an improvement of the UVA-PF of 8.4 % compared to the control sample, i.e. containing none mycosporine-like amino acid compound.
- the addition of MAA-13 in an amount of 3.0 % results even in an improvement of the UVA-PF of 30.9 % compared to the control sample, i.e.
- the addition of MAA-13 also increases the broad-spectrum protection from a critical wavelength of 374 nm to critical wavelengths of 378 nm and 379 nm depending on the concentration of the MAA-13. Hence, the addition of MAA-13 leads to an improvement of the SPF as well as of the UVA-PF in a sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprising an inorganic UV-filter in the form of an oil-in-water emulsion.
- Table 5 0 [0513]
- the in vitro SPF is highly improved by the combination of the formulation with the mycosporine-like amino acid compound MAA.
- the control example containing no mycosporine-like amino acid compound exhibited an SPF of 42.8.
- the addition of MAA-20 in an amount of 1.0 % by weight results in an 230145 in vitro SPF of 51.0 which is 19.2 % higher than the in vitro SPF of the reference sample, i.e. the control example without the addition of the mycosporine-like amino acid compound.
- the addition of MAA-20 in an amount of 1.0 % result in an improvement of the UVA-PF of 0.16 compared to the control sample, i.e. containing none mycosporine-like amino acid compound.
- the addition of MAA-20 also increases the broad-spectrum protection from a critical wavelength of 373 nm to 374 nm.
- the addition of MAA-20 leads to an improvement of the SPF as well as of the UVA-PF in a sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprising an inorganic UV-filter in the form of an oil-in-water emulsion.
- Example 1.2 - W/O ZnO emulsion [0518] The formulation samples A to E as specified in the following Table 6 and the formulation samples A and B as specified in the following Table 7 were prepared as follows: [0519] Phase A: The ingredients of phase A were heated to 85 °C without pigment in order to dissolve the ingredients. [0520] Phase A: The pigments in the oil phase were dissolved while stirring and homogenized (Ultra Turrax® T25: 10,000rpm/10 min). [0521] Phase B: The ingredients of phase B were mixed and dissolved while stirring. The water phase will be cloudy in combination with the sodium hydroxide solution. Afterwards, the water phase B is heated to 80 °C.
- the control example containing no mycosporine-like amino acid compound exhibited an SPF of 22.0.
- the addition of MAA-1 in an amount of 1.0 % by weight results in an in vitro SPF of 26.45 which is 20.2 % higher than the in vitro SPF of the reference sample, i.e. the sample without the addition of the mycosporine-like amino acid compound.
- the addition of MAA-1 in an amount of 3.0 % by weight even results in an in vitro SPF of 42.8 which is 94.5 % higher than the in vitro SPF of the control sample, i.e. containing none mycosporine-like amino acid compound.
- the addition of MAA-13 in an amount of 1.0 % results in an in vitro SPF of 25.1 which is 14 % higher than the in vitro SPF of the reference sample, i.e. the sample without the addition of the mycosporine-like amino acid compound.
- the addition of MAA13 in an amount of 3.0 % by weight even results in an in vitro SPF of 44.4 which is twice as much as the in vitro SPF of the reference sample (101.8 %), i.e. the sample without the addition of the mycosporine-like amino acid compound.
- an improved SPF results from the addition of a certain mycosporine-like amino acid compound in the sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprising an inorganic UV-filter, but also a boosted UVA-PF.
- the addition of MAA-1 in an amount of 1.0 % result in an improvement of the UVA-PF of 5.7 % compared to the control sample, i.e. containing none mycosporine-like amino acid compound.
- the addition of MAA-1 in an amount of 3.0 % results even in an improvement of the UVA-PF of 15.2 % compared to the control 230145 sample, i.e. containing none mycosporine-like amino acid compound. compared to the control sample, i.e.
- the addition of MAA-13 in an amount of 1.0 % result in an improvement of the UVA-PF of 6.5 % compared to the control sample, i.e. containing none mycosporine-like amino acid compound.
- the addition of MAA-13 in an amount of 3.0 % results even in an improvement of the UVA-PF of 30.6 % compared to the control sample, i.e. containing none mycosporine- like amino acid compound, compared to the control sample, i.e. containing none mycosporine-like amino acid compound.
- the addition of MAA-13 also increases the broad-spectrum protection from a critical wavelength of 373 nm to a critical wavelength of 379 nm and 380 nm depending on the concentration of the MAA-13.
- Table 7 Table 7:
- the in vitro SPF is highly improved by the combination of the formulation with the mycosporine-like amino acid compound MAA-20.
- the control example containing no mycosporine-like amino acid compound exhibited an SPF of 24.6.
- the addition of MAA-20 in an amount of 1.0 % by weight results in an in vitro SPF of 29.5 which is 19.9 % higher than the in vitro SPF of the reference 230145 sample, i.e. the control example without the addition of the mycosporine-like amino acid compound.
- the addition of MAA-20 leads to an improvement of the SPF in a sunscreen product, cosmetic or pharmaceutical preparation or homecare product comprising an inorganic UV-filter in the form of a water-in-oil emulsion.
- Sunscreen products, cosmetic and pharmaceutical preparations and homecare products are indicated as % by weight for all formulations: ⁇ Sunscreen Oil Spray with Ethanol, expected SPF 30, UVA/UVB balanced ⁇ Urban Sun Spray expected SPF 50+ ⁇ Sunscreen Spray (O/W), expected SPF 30 (all in one pot/cold manufacturing process) ⁇ UV protection water spray SPF 50 ⁇ Sunscreen Spray, *SPF 50+, Very Water Resistant** ⁇ Sunscreen Lotion (O/W), expected SPF 50* (cold/cold manufacturing process) ⁇ Beach Time Lotion SPF 30 ⁇ Anti-Sweat Sunscreen Lotion ⁇ Sun protection milk (w/o) ⁇ Face Protecting Watery Mousse expected SPF 30* ⁇ Full protection drops expected SPF 50 ⁇ Glow Brightener, expected SPF 50plus* ⁇ Sunscreen Fluid for acne-prone Skin, expected SPF 30 ⁇ No More Shine Fluid expected SPF50 ⁇ Light Sunscreen Fluid.
- Table F21 Refreshing Gel Sunscreen with expected SPF 30 UVA/UVB balanced 230145 [0556]
- Table F22 Sun protection balm, SPF 40 230145 [0557]
- Table F23 Anti-Pollution Hair Care (SPF 15) 230145 [0558]
- Table F24 Perfect Hand emulsion with expected SPF 15, UVA/UVB Balanced 230145 230145 [0559]
- Table F25 Tinted Sunscreen cream against hyperpigmentation 230145 [0560]
- Table F26 BB Cream Dark Tone SPF-20 (expected) 230145 [0561]
- Table F27 Daily Well Aging, with SPF 30, UVA/UVB balanced, w/o Octocrylene 230145 [0562]
- Table F28 Anti-Wrinkle Day Emulsion expected SPF 15 230145 230145 [0563]
- Table F29 Daily Tattoo Care with expected SPF 10, UVA/UVB balanced 230145 230145 [0564]
- Table F30 Sensitive Day
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Abstract
La présente invention concerne des produits d'écran solaire, des préparations cosmétiques ou pharmaceutiques ou des produits de soins à domicile ayant une protection contre les UVA et/ou les UVB comprenant un filtre UV inorganique et un certain composé acide aminé de type mycosporine. Les produits et les préparations fournissent une performance de facteur de protection solaire (FPS) améliorée et une photoprotection contre les UVA améliorée. De plus, les produits et les préparations selon la présente invention fournissent une photoprotection à large spectre contre les rayons UV. Également, la présente invention concerne l'utilisation d'un tel composé acide aminé de type mycosporine pour stimuler le facteur de protection solaire et/ou la photoprotection contre les UVA d'un produit d'écran solaire, d'une préparation cosmétique ou pharmaceutique ou d'un produit de soins à domicile comprenant un filtre UV organique. En outre, la présente invention concerne un procédé d'amélioration du facteur de protection solaire et de la photoprotection contre les UVA d'un produit d'écran solaire, d'une préparation cosmétique ou pharmaceutique ou d'un produit de soins à domicile comprenant un filtre UV inorganique par l'addition d'un certain composé d'acide aminé de type mycosporine. Enfin, la présente invention concerne un procédé pour apporter des bénéfices anti-vieillissement à la peau, blanchir ou prévenir l'assombrissement de la peau, améliorer l'aspect de la peau, diminuer les signes visibles du vieillissement de la peau et améliorer l'éclat et la fermeté de la peau par application topique sur la peau du produit d'écran solaire, de la préparation cosmétique ou pharmaceutique ou du produit de soins à domicile selon la présente invention.
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PCT/EP2022/072097 WO2024027928A1 (fr) | 2022-08-05 | 2022-08-05 | Composition à fps et photoprotection contre les uva améliorés |
EPPCT/EP2022/072097 | 2022-08-05 | ||
EP2023071719 | 2023-08-04 | ||
EPPCT/EP2023/071719 | 2023-08-04 |
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002039974A1 (fr) * | 2000-11-17 | 2002-05-23 | Natural Environment Research Council | Compositions de soins personnels |
WO2004026840A1 (fr) | 2002-09-18 | 2004-04-01 | Unilever Plc | Derives de tetrahydropyrimidine-2-one et leurs utilisations |
WO2004047833A2 (fr) | 2002-11-25 | 2004-06-10 | Symrise Gmbh & Co. Kg | Amides d'acide anthranilique et leurs derives utilises comme principes actifs cosmetiques et pharmaceutiques |
WO2013181741A1 (fr) * | 2012-06-04 | 2013-12-12 | Elkimia | Composés imino comme agents protecteurs contre rayonnements ultraviolets |
WO2015195546A1 (fr) * | 2014-06-17 | 2015-12-23 | TopGeniX, Inc. | Formulations topiques de protection contre les uv |
KR20190076425A (ko) * | 2017-12-22 | 2019-07-02 | 코스맥스 주식회사 | 자외선 차단용 화장료 조성물 |
WO2021168582A1 (fr) * | 2020-02-26 | 2021-09-02 | elkimia inc. | Procédé de synthèse de composés qui absorbent le rayonnement ultraviolet dans des conditions d'écoulement et formulations les comprenant |
-
2023
- 2023-08-07 WO PCT/EP2023/071792 patent/WO2024028514A1/fr unknown
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002039974A1 (fr) * | 2000-11-17 | 2002-05-23 | Natural Environment Research Council | Compositions de soins personnels |
WO2004026840A1 (fr) | 2002-09-18 | 2004-04-01 | Unilever Plc | Derives de tetrahydropyrimidine-2-one et leurs utilisations |
WO2004047833A2 (fr) | 2002-11-25 | 2004-06-10 | Symrise Gmbh & Co. Kg | Amides d'acide anthranilique et leurs derives utilises comme principes actifs cosmetiques et pharmaceutiques |
WO2013181741A1 (fr) * | 2012-06-04 | 2013-12-12 | Elkimia | Composés imino comme agents protecteurs contre rayonnements ultraviolets |
WO2015195546A1 (fr) * | 2014-06-17 | 2015-12-23 | TopGeniX, Inc. | Formulations topiques de protection contre les uv |
KR20190076425A (ko) * | 2017-12-22 | 2019-07-02 | 코스맥스 주식회사 | 자외선 차단용 화장료 조성물 |
WO2021168582A1 (fr) * | 2020-02-26 | 2021-09-02 | elkimia inc. | Procédé de synthèse de composés qui absorbent le rayonnement ultraviolet dans des conditions d'écoulement et formulations les comprenant |
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