MXPA06008185A - Retinoid-containing preparations - Google Patents
Retinoid-containing preparationsInfo
- Publication number
- MXPA06008185A MXPA06008185A MXPA/A/2006/008185A MXPA06008185A MXPA06008185A MX PA06008185 A MXPA06008185 A MX PA06008185A MX PA06008185 A MXPA06008185 A MX PA06008185A MX PA06008185 A MXPA06008185 A MX PA06008185A
- Authority
- MX
- Mexico
- Prior art keywords
- weight
- soluble
- acid
- water
- oil
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 52
- 150000004492 retinoid derivatives Chemical class 0.000 title claims abstract description 16
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 39
- 230000000111 anti-oxidant Effects 0.000 claims abstract description 29
- 239000004904 UV filter Substances 0.000 claims abstract description 23
- 230000003078 antioxidant Effects 0.000 claims abstract description 10
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 42
- 235000006708 antioxidants Nutrition 0.000 claims description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 239000002537 cosmetic Substances 0.000 claims description 21
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Vitamin C Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 20
- 229960005070 ascorbic acid Drugs 0.000 claims description 20
- 239000000839 emulsion Substances 0.000 claims description 17
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 16
- CIWBSHSKHKDKBQ-DUZGATOHSA-N (+)-Ascorbic acid Natural products OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 claims description 12
- 239000002211 L-ascorbic acid Substances 0.000 claims description 10
- 235000000069 L-ascorbic acid Nutrition 0.000 claims description 10
- 239000011780 sodium chloride Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 210000003491 Skin Anatomy 0.000 claims description 7
- 229960000984 tocofersolan Drugs 0.000 claims description 5
- 229940100609 All-Trans-Retinol Drugs 0.000 claims description 4
- 235000019169 all-trans-retinol Nutrition 0.000 claims description 4
- 239000011717 all-trans-retinol Substances 0.000 claims description 4
- 229940087168 alpha Tocopherol Drugs 0.000 claims description 4
- 239000002076 α-tocopherol Substances 0.000 claims description 4
- 235000004835 α-tocopherol Nutrition 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 230000001681 protective Effects 0.000 claims description 3
- 235000002639 sodium chloride Nutrition 0.000 claims 1
- -1 thio compound Chemical class 0.000 description 42
- 229960003471 retinol Drugs 0.000 description 19
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 16
- 235000020944 retinol Nutrition 0.000 description 15
- 239000011607 retinol Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 229910002012 Aerosil® Inorganic materials 0.000 description 14
- 239000000049 pigment Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- CXQXSVUQTKDNFP-UHFFFAOYSA-N Simethicone Chemical class C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 10
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 10
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 10
- 235000010323 ascorbic acid Nutrition 0.000 description 9
- 239000011668 ascorbic acid Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000002304 perfume Substances 0.000 description 8
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-α-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 7
- WSSJONWNBBTCMG-UHFFFAOYSA-N Homosalate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C1=CC=CC=C1O WSSJONWNBBTCMG-UHFFFAOYSA-N 0.000 description 7
- 229960001295 Tocopherol Drugs 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 235000010384 tocopherol Nutrition 0.000 description 7
- 239000011732 tocopherol Substances 0.000 description 7
- 229930003799 tocopherols Natural products 0.000 description 7
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl methoxycinnamate Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 description 6
- 229960005055 SODIUM ASCORBATE Drugs 0.000 description 6
- GLDOVTGHNKAZLK-UHFFFAOYSA-N Stearyl alcohol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
- 229960001452 alpha-Tocopherol Acetate Drugs 0.000 description 6
- 239000006071 cream Substances 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 235000010378 sodium ascorbate Nutrition 0.000 description 6
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229940072107 Ascorbate Drugs 0.000 description 5
- TYQCGQRIZGCHNB-JLAZNSOCSA-N L-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000004359 castor oil Substances 0.000 description 5
- 235000019438 castor oil Nutrition 0.000 description 5
- 229940081733 cetearyl alcohol Drugs 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000004205 dimethyl polysiloxane Substances 0.000 description 5
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 5
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 5
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229960001679 octinoxate Drugs 0.000 description 5
- 239000004408 titanium dioxide Substances 0.000 description 5
- 239000011787 zinc oxide Substances 0.000 description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
- CWLGEPSKQDNHIO-JOBJLJCHSA-N (E)-N-[(E)-benzylideneamino]-1-phenylmethanimine Chemical compound C=1C=CC=CC=1/C=N/N=C/C1=CC=CC=C1 CWLGEPSKQDNHIO-JOBJLJCHSA-N 0.000 description 4
- 229940095259 Butylated Hydroxytoluene Drugs 0.000 description 4
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 4
- SNPLKNRPJHDVJA-UHFFFAOYSA-N DL-Panthenol Chemical compound OCC(C)(C)C(O)C(=O)NCCCO SNPLKNRPJHDVJA-UHFFFAOYSA-N 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 4
- 229940045997 Vitamin A Drugs 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- 229910001929 titanium oxide Inorganic materials 0.000 description 4
- 235000019155 vitamin A Nutrition 0.000 description 4
- 239000011719 vitamin A Substances 0.000 description 4
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-Triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 3
- 229940063655 Aluminum stearate Drugs 0.000 description 3
- UBNYRXMKIIGMKK-RMKNXTFCSA-N Amiloxate Chemical compound COC1=CC=C(\C=C\C(=O)OCCC(C)C)C=C1 UBNYRXMKIIGMKK-RMKNXTFCSA-N 0.000 description 3
- 229920001661 Chitosan Polymers 0.000 description 3
- 229960004881 Homosalate Drugs 0.000 description 3
- 239000004166 Lanolin Substances 0.000 description 3
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Octyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 3
- DXGLGDHPHMLXJC-UHFFFAOYSA-N Oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 3
- 239000005662 Paraffin oil Substances 0.000 description 3
- SHGAZHPCJJPHSC-YCNIQYBTSA-N Retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- WXQWKYFPCLREEY-UHFFFAOYSA-O azanium;ethanol Chemical class [NH4+].CCO.CCO.CCO WXQWKYFPCLREEY-UHFFFAOYSA-O 0.000 description 3
- FQLQNUZHYYPPBT-UHFFFAOYSA-O azanium;potassium Chemical compound [NH4+].[K+] FQLQNUZHYYPPBT-UHFFFAOYSA-O 0.000 description 3
- 125000004432 carbon atoms Chemical group C* 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000875 corresponding Effects 0.000 description 3
- 229940008099 dimethicone Drugs 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N edta Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 230000002209 hydrophobic Effects 0.000 description 3
- 235000019388 lanolin Nutrition 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
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- 239000004200 microcrystalline wax Substances 0.000 description 3
- 235000019808 microcrystalline wax Nutrition 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
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- 235000019271 petrolatum Nutrition 0.000 description 3
- 229920001888 polyacrylic acid Polymers 0.000 description 3
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- VBICKXHEKHSIBG-UHFFFAOYSA-N rac-1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 3
- 229930002330 retinoic acid Natural products 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
- 239000002562 thickening agent Substances 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- OIQXFRANQVWXJF-QBFSEMIESA-N (2Z)-2-benzylidene-4,7,7-trimethylbicyclo[2.2.1]heptan-3-one Chemical class CC1(C)C2CCC1(C)C(=O)\C2=C/C1=CC=CC=C1 OIQXFRANQVWXJF-QBFSEMIESA-N 0.000 description 2
- MCPKSFINULVDNX-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-methylphenol Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 2
- UVCJGUGAGLDPAA-UHFFFAOYSA-N 2-phenyl-3H-benzimidazole-5-sulfonic acid Chemical compound N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 UVCJGUGAGLDPAA-UHFFFAOYSA-N 0.000 description 2
- YDIYEOMDOWUDTJ-UHFFFAOYSA-M 4-(dimethylamino)benzoate Chemical compound CN(C)C1=CC=C(C([O-])=O)C=C1 YDIYEOMDOWUDTJ-UHFFFAOYSA-M 0.000 description 2
- CWSZBVAUYPTXTG-UHFFFAOYSA-N 5-[6-[[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxymethyl]-3,4-dihydroxy-5-[4-hydroxy-3-(2-hydroxyethoxy)-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxyoxan-2-yl]oxy-6-(hydroxymethyl)-2-methyloxane-3,4-diol Chemical compound O1C(CO)C(OC)C(O)C(O)C1OCC1C(OC2C(C(O)C(OC)C(CO)O2)OCCO)C(O)C(O)C(OC2C(OC(C)C(O)C2O)CO)O1 CWSZBVAUYPTXTG-UHFFFAOYSA-N 0.000 description 2
- VLPFTAMPNXLGLX-UHFFFAOYSA-N Axona Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 2
- RGZSQWQPBWRIAQ-CABCVRRESA-N Bisabolol Chemical compound CC(C)=CCC[C@](C)(O)[C@H]1CCC(C)=CC1 RGZSQWQPBWRIAQ-CABCVRRESA-N 0.000 description 2
- CIWBSHSKHKDKBQ-MVHIGOERSA-N D-ascorbic acid Chemical compound OC[C@@H](O)[C@@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-MVHIGOERSA-N 0.000 description 2
- NZZIMKJIVMHWJC-UHFFFAOYSA-N Dibenzoylmethane Chemical class C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 description 2
- AKNXMRHLLPIDLY-UHFFFAOYSA-N Diethylamino hydroxybenzoyl hexyl benzoate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)C1=CC=CC(N(CC)CC)=C1O AKNXMRHLLPIDLY-UHFFFAOYSA-N 0.000 description 2
- 229960001275 Dimeticone Drugs 0.000 description 2
- RFVNOJDQRGSOEL-UHFFFAOYSA-N Glycol stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 2
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- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 229940039717 Lanolin Drugs 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N Lauric acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- OAIJSZIZWZSQBC-LWRKPGOESA-N Lycopene Natural products CC(C)=CCC\C(C)=C/C=C/C(/C)=C\C=C\C(\C)=C/C=C/C=C(/C)\C=C\C=C(\C)/C=C/C=C(/C)CCC=C(C)C OAIJSZIZWZSQBC-LWRKPGOESA-N 0.000 description 2
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- IPCSVZSSVZVIGE-UHFFFAOYSA-N Palmitic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L Sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 229960001727 Tretinoin Drugs 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
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- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
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- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
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- WXNRYSGJLQFHBR-UHFFFAOYSA-N bis(2,4-dihydroxyphenyl)methanone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1O WXNRYSGJLQFHBR-UHFFFAOYSA-N 0.000 description 2
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- 239000000975 dye Substances 0.000 description 2
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- 125000004430 oxygen atoms Chemical group O* 0.000 description 2
- 229920000059 polyethylene glycol stearate Polymers 0.000 description 2
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- 230000002335 preservative Effects 0.000 description 2
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- 108090000765 processed proteins & peptides Proteins 0.000 description 2
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Abstract
The invention relates to preparations containing a) at least one type of retinoid, b) at least one type of water-soluble antioxidant, c) at least one type of oil-soluble antioxidant and d) at least 0.01 to 10%by weight of UV filter. Said invention is characterised in that the inventive preparations contain at least 1 part by weight of one or several water-soluble antioxidants and 0.1 to 100 parts by weight of one or several oil-soluble antioxidants per part by weight of retinoid, the content of one or several water-soluble antioxidants ranging from 0.05 to 0.8%by weight with respect to the total quantity of the preparations.
Description
PREPARATIONS CONTAINING RETINOIDS
The present invention relates to preparations containing retinoids, their preparation and use in cosmetics and pharmacy.
Retinoids are some of the most active ingredients used in cosmetics and dermatology, these have, among others, a regulatory effect on the growth of normal cells and influence the differentiation of epithelial cells. The retinoic acids are thus used for the treatment of acne, and retinol is used in anti-wrinkle creams.
However, the use of retinoids is very restricted, which can be attributed, among other things, to the high instability of the compounds. For this reason, rigorous safety precautions have been observed during the production of the retinoid-containing preparations. For example, the production can be carried out completely under protective gas, and the finished product must be packed in light and oxygen impermeable packaging.
These requirements require the manufacturer to have complex technology equipment and in this way are associated with high production costs.
Some methods to stabilize retinoids have been described. For example, EP-A-1 056 720 describes the stabilization of oxygen sensitive compounds using thio compound or glycoproteins with the exclusion of oxygen.
According to WO 93/00085 and EP-A-0 440 398, the antioxidants soluble in water and also in fats are used together with chelating agents for the stabilization of retinoids.
However, the described methods do not always lead to adequate stabilization for the purpose of the invention. In contrast, water-soluble antioxidants, in particular ascorbic acid, and fat-soluble antioxidants, in particular tocopherol, have a destabilizing effect in relation to retinoids in some concentration ranges.
In addition, in some cases, the use of some antioxidant combinations together with the retinoids may give rise to unwanted side effects, for example, yellowish discolorations of the preparations, which makes the use of these systems in the cosmetics sector unlikely or in food.
Therefore, an object of the present invention was to provide preparations containing retinoids which do not have the disadvantages mentioned above with respect to stability and discoloration, and which can be produced in a simple form.
The goal is achieved through preparations that contain:
to. at least one retinoid,
b. at least one water-soluble antioxidant,
c. at least one oil-soluble antioxidant and
d. 0.01 to 10% by weight of at least one UV filter.
wherein, in the preparations, for each part by weight of retinoid there is present at least one part by weight of one or more water-soluble antioxidants and 0.1 to 100 parts by weight of one or more oil-soluble antioxidants, wherein the content of one or more water-soluble antioxidants is in the range from 0.05 to 0.8% by weight, based on the total amount of the preparations.
The preparations according to the invention are pharmaceutical cosmetic and dermatological preparations. Preference is given to cosmetic preparations, in particular preparations for skin care.
An advantageous embodiment of the preparations according to the invention contains, by weight of the retinoid, 1 to 100 parts by weight, preferably 1 to 20 parts by weight, particularly preferably 1 to 6 parts by weight, very particularly preferably 3 to 5 parts by weight of one or more water-soluble antioxidants, and 1 to 20 parts by weight, preferably 1 to 15 parts by weight, particularly preferably 1 to 10 parts by weight, very particularly preferably 3 to 5 parts by weight by weight of one or more oil soluble antioxidants.
For the purpose of the present invention, retinoids means the alcohol of vitamin A (retinol) and its derivatives, such as the aldehyde of vitamin A (retinal), the acid of vitamin A (retinoic acid) and esters of vitamin A, such as retinyl acetate and retinyl palmitate. The term "retinoic acid" herein consists of all-trans retinoic acid and 13-cis-retinoic acid. The terms retinol and retinal preferably comprise the all trans compounds. The preferred retinoid used for the preparations according to the invention is all-trans-retinol.
The proposed water-soluble antioxidants are, among others, ascorbic acid, sodium sulfite, sodium metabisulfite, sodium bisulfite, sodium thiosulfite, formaldehyde sodium sulfoxide, isoascorbic acid, thioglycerol, thiosorbitol, thiourea, thioglycolic acid, cysteine hydrochloride. , 1,4-diazobicyclo (2,2,2) octane and mixtures thereof.
Preferred water soluble antioxidants are ascorbic acid (L-ascorbic acid) and isoascorbic acid (D-ascorbic acid), particularly preferably L-ascorbic acid.
The L-ascorbic acid which is used with particular preference may be the free acid or even the salts thereof. Examples of the salts of L-ascorbic acid are the alkali metal or alkaline earth metal salts of L-ascorbic acid, such as sodium L-ascorbate, potassium L-ascorbate or calcium L-ascorbate, but also salts of L-ascorbic acid with an organic amino compound, such as choline ascorbate or L-carnitine ascorbate. Particular preference is given to the use of free L-ascorbic acid or sodium L-ascorbate. The corresponding statements apply to the use of D-ascorbic acid.
The proposed oil-soluble antioxidants include, but are not limited to, butylated hydroxytoluene (BHT), ascorbyl palmitate, butylated hydroxyanisole, α-tocopherol, phenyl-α-naphthylamine or mixtures thereof.
A preferred oil-soluble antioxidant is α-tocopherol, which may be (R, R, R) - or (all-rae) -a-tocopherol.
For the purpose of the present invention, UV filter means UV-A, UV-B and / or wide-band filters.
Advantageous broadband filters, UV-A or UV-B filter substances are, for example, representative of the following classes of compounds: bis-resorcinyltriazine derivatives with the following structure:
where R1, R2 and R3, independent of each other, are chosen from branched and unbranched alkyl groups having 1 to 10 carbon atoms or 1 individual hydrogen atoms. Particular preference is given to compound 2, -bis-. { [4- (2-ethylhexyloxy) -2-hydroxy] phenyl} -6- (4-methoxyphenyl) -1,3,5-triazine (INCI: Aniso Triazine), which is available under the trademark Tinosorb® S from CIBA-Chemikalien GmbH.
Other UV filter substances, which have the structural motif:
also are their advantageous UV filter substances within the meaning of the present invention, for example, the S-triazine derivatives described in the European specification open to the public EP 570 838 Al, the chemical structure that is given by the generic formula:
where :
R is a branched or unbranched Ci-Ciß alkyl radical, a C5-C12 cycloalkyl radical, optionally substituted by one or more C1-C4 alkyl groups.
X is an oxygen atom or an NH group,
Ri is a branched or unbranched C? -Ci8 alkyl radical, a C5-C12 cycloalkyl radical? optionally substituted by one or more C3-C4 alkyl groups, or a hydrogen atom, an alkali metal atom, an ammonium group or a group of the formula:
in which:
A is a branched or unbranched C? -Ci8 alkyl radical, a C5-C12 cycloalkyl radical or aryl, optionally substituted by one or more C1-C4 alkyl groups.
R3 is a hydrogen atom or a methyl group,
n is a number from 1 to 10,
R2 is a branched or unbranched Ci-Cis alkyl radical, a C5-C12 cycloalkyl radical, optionally substituted by one or more C1-C4 alkyl groups, if X is the NH group, a branched C1-C18 alkyl radical or unbranched, a C5-C12 cycloalkyl radical, optionally substituted by one or more C1-C alkyl groups or a hydrogen atom, an alkali metal atom, an ammonium group or a group of the formula:
in which:
A is a branched or unbranched Ci-Ciß alkyl radical, a C5-C12 cycloalkyl radical or aryl radical, optionally substituted by one or more C1-C4 alkyl groups.
R3 is a hydrogen atom or a methyl group,
n is a number from 1 to 10,
if X is an oxygen atom.
A particularly preferred UV filter substance within the meaning of the present invention is also an asymmetrically substituted s-triazine whose chemical structure is given by the formula:
which is also referred to later as dioctylbutyl to idotriazone (INCI: diethylhexylbutanedi triazone) and is available with the brand UVASORB® HEB from Sigma 3V.
Also advantageous within the meaning of the present invention is an s-triazine, symmetrically substituted, tris (2-ethylhexyl) 4 ', 4"- (1, 3, 5-triazine-2, 4, 6-triazine-2 ,, 6-triiltriiamino) trisbenzoato, syn: 2, 6-tris [anilino (p-carbo-2'-ethyl-1'-hexyloxy)] -1, 3, 5-triazine (INCI: Ethylhexyl triazone) sold by BASF Aktiengesellschaft under the brand UVINUL® T 150.
The European specification open to the public 775 698 also describes derivatives of bisresorcinyltriazine to be used with preference, the chemical structure of which is given by the generic formula:
where Ri and R2 are, inter alia, C3-C18 alkyl or C2-C18 alkenyl and i is an aromatic radical.
Also advantageous for the purpose of the present invention are 2, 4-bis. { [4- (3-sulfonate) -2-hydroxypropyloxy) -2-hydroxy] phenyl} -6- (4-methoxyphenyl) -1,3,5-triazine, the sodium salt, 2, 4-bis. { [4- (3- (2-propyloxy) -2-hydroxypropyloxy) -2-hydroxy] phenyl} -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4-bis. { 4- (2-ethylexyloxy) -2-hydroxy] phenyl} -6- [(2-methoxyethylcarboxyl) phenylamine] -1,3,5-triazine, 2,4-bis. { [4- (3- (2-propyloxy) -2-hydroxypropyloxy) -2-hydroxyphenyl} -6- (4- (2-ethylcarboxyl) phenylamine] -1,3,5-triazine, 2,4-bis { [4- (2-ethylhexyloxy) -2-hydroxy] phenyl] -6- (l-methylpyrrole-2-yl) -1,3,5-triazine, 2,4-bis { [4-tris (trimetilsiloxisililpropiloxi) -2-hydroxy] -phenyl.}. -6- (4-methoxyphenyl ) -l, 3,5-triazine, 2,4-bis { [4- (2"-methylpropenyloxy) -2-hydroxy] phenyl.}. -6- (4-methoxyphenyl) -1,3,5 -triazine, and 2, 4-bis { [4- (1 ', 1', 1 ', 3', 5 ', 5', 5 '-heptamethylsiloxy-2"-methylpropyloxy) -2-hydroxy] phenyl.}. -6- (4-methoxyphenyl) -1,3,5-triazine.
Water soluble, sulfonated UV filters, advantageous for the purpose of the present invention are:
phenylene-1,4-bis (2-benzimidazyl) -3,3 '-5,5'-tetrasulfonic acid, which is characterized by the following structure:
and their salts, particularly the corresponding sodium, potassium and triethanolammonium salts, in particular the bis-sodium salt of phenylene-1,4-bis (2-benzimidazyl) -3,3'-5, 5'-tetra-sulphonic acid.
with the INCI name bisimidazilate (CAS No .: 180898-37-7), which can be obtained, for example, with the Neo Heliopan® AP from Haarmann & Reimer
Another UV filter sulfonated advantageous for the purpose of the present invention are salts-phenylbenzimidazole-5-sulphonic acid 2, such as its sodium, potassium or triethanolammonium salt, and the sulphonic acid itself:
with the name INCI phenylbenzimidazole sulfonic acid (CAS No .: 27503-81-7), which can be obtained, for example, under the trademark Eusolex® 232 from Merck or with the Neo Heliopan® Hydro from Haarmann & Reimer
Another UV filter sulfonated advantageous is 3, 3 '- (1, 4-fenilendimetilen) bis (7, 7-dimethyl-2-oxo-bicyclo [2.2.1] hept-1-ilmetansulfónico, such as its sodium salt , potassium or triethanolammonium, and the sulphonic acid itself:
with the name INCI acid tereftaliden dicamfor sulphonic (CAS No .: 90457-82-2), which can be obtained, for example, from the brand Mexoryl® SX Chimex.
Another UV-B and / or broadband filter soluble in water, the substances are advantageous, for example:
sulphonic acid derivatives of 3-benzilidencanfor, such as for example 4- (2-oxo-3-bornylidenemethyl) benzenesulfonic acid, 2-methyl-5- (2-oxo-3-bornylidenemethyl) sulphonic acid and salts these.
UV-B and / or wide-band filters can be oil-soluble or water-soluble. Advantageous oil-soluble UV-B and / or wide-band filter substances are, for example: 3-benzylidenecamphor derivatives, preferably 3- (4-methylbenzylidene) camphor, 3-benzylidenecamphor;
4-aminobenzoic acid derivatives, preferably 4- (dimethylamino) benzoate of (2-ethylhexyl), 4- (dimethylamino) benzoate of amyl, 4-bis (polyethoxy) aminobenzoate of polyethoxyethyl (can be obtained under the trademark Uvinul® P25 from BASF );
benzophenone derivatives, preferably 2-hydroxy-4-methoxybenzophenone (obtainable from the Uvinul® M40 trademark of BASF), 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone, acid 2-hydroxy-4-methoxybenzophenone-5-sulphonic acid (available from Uvinul® MS40 from BASF), 2, 2 ', 4,4'-tetrahydroxybenzophenone (available from Uvinul® D 50 from BASF);
UV filters attached to polymers.
For the purpose of the present invention, particularly advantageous UV filter substances which are liquid at room temperature are homomenthyl salicylate, 2-cyano-3, 3-diphenylacrylate 2-ethylhexyl, ethylhexyl 2-hydroxybenzoate and cinnamic acid esters, preferably 2-methylhexyl 4-methoxycinnamate and isopentyl 4-methoxycinnamate.
Homomenthyl salicylate (INCI: homosalate) is characterized by the following structure.
2-cyano-3, 3-diphenylacrylate 2-ethylhexyl (INCI: octocrylene) can be obtained from BASF under the brand name Univul® N 539T and is characterized by the following structure:
2-ethylhexyl 2-hydroxybenzoate (2-ethylhexyl salicylate, octyl salicylate, INCI: ethylhexyl salicylate) can be obtained, for example, from Arman & Reimer with the Neo Heliopan® OS brand and is characterized by the following structure:
2-ethylhexyl 4-methoxycinnamate (INCI: ethylhexyl methoxycinnamate) can be obtained, for example, from BASF under the trademark Uvinul® MC 80 and is characterized by the following structure:
Isopentyl 4-methoxycinnamate (INCI: isoamyl p-methoxycinnamate) can be obtained, for example, from Arman & Reimer with the Neo Heliopan® E 1000 brand and is characterized by the following structure:
For the purpose of the present invention, another advantageous UV filter substance which is liquid at room temperature (copolymer of (3- (4- (2,2, -bisetoxycarbonylvinyl) phenoxy) propenyl) -methylsiloxane / dimethylsiloxane, obtainable by example of Hoffmann-La Roche with the Parsol® SLX brand.
For the purposes of the present invention, the advantageous dibenzoylmethane derivatives are in particular 4- (tert-butyl) -4'-methoxydibenzoylmethanol (CAS No. 70356-09-1), which is marketed by BASF under the trademark Uvinul® BMBM and by Merck with the Eusolex® 9020 brand, which is characterized by the following structure:
Another advantageous dibenzoylmethane derivative is a 4-isopropyldibenzoylmethane (CAS No. 63250-25-9), which is marketed by Merck under the trademark Eusolex® 8020. Eusolex® 8020 is characterized by the following structure:
The benzotriazoles are characterized by the following structural formula:
in which:
R1 and R2, independent of each other, can be linear or branched alkyl radicals, saturated or unsaturated, substituted (for example substituted by a phenyl radical) or unsubstituted, having 1 to 18 carbon atoms and / or polymeric radicals by themselves they do not absorb UV rays (such as silicon radicals, acrylate radicals and the like), and R3 is selected from the group H or alkyl radical having from 1 to 18 carbon atoms.
For the purpose of the present invention, an advantageous benzotriazole is 2,2 '-methylenebis (6- (2H-benzotriazol-2-yl) -4- (1,1,3,3-tetramethylbutyl) phenol), a filter of broad band that is characterized by the chemical structural formula:
can be obtained from the Tinosorb® M brand of Ciba Chemikalien GmbH.
For the purpose of the present invention, another advantageous bezotriazole is 2- (2H-bezotriazol-2-yl) -4-methyl-6- [2-methyl-3- [1, 3, 3, 3-tetramethyl-l- [(trimethylsilyl) oxy] disiloxanyl] propyl] -phenol (CAS No .: 155633-54-8) under the name INCI Drometrizol Trisiloxane, which is marketed by Chimex under the trademark Mexoryl® XL and is characterized by the following structural chemical formula :
For the purpose of the present invention, other advantageous benzotriazoles are: [2, '-dihydroxy-3- (2H-benzotriazol-2-yl) -5- (1, 1, 3, 3-tetramethylbutyl) -2'-N -octoxy-5'-benzoyl] diphenyl-methane, 2,2 '-methylenebis [6- (2H-bezotriazol-2-yl) -4- (methyl) phenol], 2'-2-methylenebis- [6- ( 2H-benzotriazol-2-yl) -4- (1,1,3,3-tetramethylbutyl) phenol], 2- (2'-hydroxy-5'-octyl-phenyl) benzotriazole, 2- (2'-hydroxy) 3 ', 5' -di-t-amylphenyl) benzotriazole and 2- (2'-hydroxy-5'-methylphenyl) benzotriazole.
For the purpose of the present invention, another advantageous UV filter is the diphenylbutadiene compound of the following formula described in EP-A-0 916 335.
For the purpose of the present invention, another advantageous UV-A filter is diethyl 2- (4-ethoxyanilinomethylene) propanedicarboxylate of the following formula described in EP-A-0 895 776.
Likewise, advantageous for the purposes of the present invention, is a hydroxybenzophenone substituted with anaino of the following formula:
which is marketed by BASF Aktioengelsellschanft as a UV-A filter with the UVINUL® A Plus brand.
The cosmetic and dermatological preparations according to the invention also advantageously, although not necessarily, contain inorganic pigments based on metal oxides and / or other metal compounds which are sparingly soluble or insoluble in water, in particular titanium oxides (TiO2), zinc (ZnO), iron (for example Fe2 or 3), zirconium (Zr? 2), silicon (SIO2), manganese (for example MnO), aluminum (AI2O3), cerium (for example C? 2? 3), mixed oxides of the corresponding metals and mixtures of these oxides. These pigments are amorphous to X-rays and amorphous not to X-rays. These are particularly preferred pigments based on TiO2.
X-ray amorphous oxide pigments are metal oxides or semi-metallic oxides that, in X-ray diffraction experiments, do not reveal recognizable or non-recognizable crystal structures. These pigments can often be obtained by reaction to the flame, reacting a metal halide or semimetal halides with hydrogen and air (or pure oxygen) in a flame.
In cosmetic, dermatological or pharmaceutical formulations, amorphous X-ray oxide pigments are used as thickeners and thixotropic agents, flow aids, for stabilization of emulsions and dispersions and as carrier substances (for example to increase the volume of finely divided powders) .
The amorphous oxide pigments known to X-rays and often used in cosmetic or dermatological medicaments are silicon oxides of the Aerosil® type (CAS No. 7631-86-9). The Aerosil®, which can be obtained from DEGUSSA, are characterized by small particle size (for example between 5 and 40 nm) where the particles are considered as spherical particles of very uniform dimension. At first sight, Aerosil® can be observed as white, loose powders. For the purpose of the present invention, X-ray amorphous silicon dioxide pigments are particularly advantageous, and among these in particular those of the Aerosil® type are preferred.
Advantageous Aerosil® grades are for example Aerosil® OX50, Aerosil® 130, Aerosil® 150, Aerosil® 200, Aerosil® 300, Aerosil® 380, Aerosil® MOX 80, Aerosil® MOX 170, Aerosil® COK 84, Aerosil® R 202, Aerosil® R 805, Aerosil® R 812, Aerosil® R 972, Aerosil® 974, Aerosil® R 976.
According to the invention, the inorganic, amorphous, non-X-ray pigments are advantageously hydrophobic, ie they have been surface treated to repel water. This surface treatment may consist in providing the pigments with a thin hydrophobic layer by the methods already known.
One method is, for example, to produce the surface hydrophobic layer by a reaction in accordance with:
n Ti02 + m (RO) 3 Si-R '? n Ti02 (surf.)
n and m in this case are stoichiometric parameters that are used as desired, R and R 'are the desired organic radicals. Hydrophobized pigments, synthesized, for example, in accordance with DE-A 33 14 743 are advantageous.
For the purpose of the present invention, organic surface coatings may consist of vegetable or animal aluminum stearate, vegetable or animal stearic acid, lauric acid, dimethyl polysiloxane (also dimethicone), methyl polysiloxane (methicone), simethicone (a mixture of dimethyl polysiloxane with an average chain length from 200 to 350 units of dimethylsiloxane and silica gel), octyltrimethoxysilane or alginic acid. These organic surface coatings can be used as they are, in combination and / or in combination with inorganic coating materials.
The zinc oxide particles and the previous dispersions of zinc oxide particles suitable according to the invention can be obtained from the following brands and from the aforementioned companies.
The suitable titanium dioxide particles and the previous dispersions of the titanium dioxide particles can be obtained from the following brands and from the following listed companies:
Advantageous TiO2 pigments can be obtained, for example, from the Uvinul® TIO2 brand, the advantageous Ti02 / Fe2 + 3 mixed oxides of the Uvinul® Ti02 A brand from BASF.
The total amount of at least one UV filter used in the finished cosmetic or dermatological preparations is advantageously chosen from the range from 0.01 to 10% by weight, preferably in the range from 0.5 to 8% by weight, with particular preference in the range from 1 to 7% by weight, based on the total weight of the preparations.
The UV filters present in the preparations according to the invention can be used in this case to stabilize retinol (protection of the product) and to protect human skin against UV radiation
(skin care) .
For use as protection of the product, the necessary amount of the UV filters that can be used is much smaller and for these cases it is advantageously in the range from 0.01 to 0.5% by weight, preferably in the range from 0.05 to 0.1%, based on the total weight of the preparations.
The UV filters that would be mentioned as preferred for use in the preparations according to the invention are the following: the Uvinul® brands of BASF: Uvinul® A Plus, Uvinul® D 50 Uvinul® M 40, Uvinul® MS 40, Uvinul® P 25, Uvinul® MC 80, Uvinul® N 539, Uvinul® T150, and inorganic pigments TiO 2, and ZnO.
In particular, for use as protection of the product, the following UV filters can be mentioned: Uvinul® A Plus, Uvinul® D 50 Uvinul® M 40, Uvinul® MS 40, Uvinul® MS 40 and Uvinul® P 25.
The preparations according to the invention normally contain 0.015 to 0.2% by weight, preferably 0.02 to 0.15% by weight, with particular preference 0.03 to 0.15% by weight, most particularly preferably 0.04 to 0.12% by weight, of one or more retinoids , in particular all trans retinol, 0.05 to 0.8% by weight, preferably 0.08 to 0.7% by weight, particularly preferably 0.12 to 0.6% by weight, with very particular preference 0.16 to 0.5% by weight of one or more antioxidants soluble in water, in particular L-ascorbic acid and 0.005 to 2% by weight, preferably 0.01 to 1.8% by weight, particularly preferably 0.1 to 1.5% by weight, with very particular preference 0.15 to 1.2% by weight of one or more antioxidants soluble in oil, in particular α-tocopherol.
The preparations according to the invention are characterized, among other things, in that it is possible to omit the use of protective gas during its production, filling and storage while guaranteeing adequate stability. ,
For the purposes of the present invention, by suitable stability it is meant that the retinoid is again in an amount of at least 90% in the preparation after storage for 12 weeks at 40 ° C. In addition, no unwanted color changes are observed during the storage of the preparations according to the invention.
It is convenient that the preparations according to the invention are stored in oxygen-impermeable containers.
Oxygen-impermeable containers can be any normal commercial container, suitable for this purpose, such as glass containers or aluminum containers.
Another advantage of the preparations according to the invention is that these products no longer have to be stored excluding light.
By comparison with the previously known retinoid-containing cosmetic preparations, when the preparations according to the invention are used in the care of the skin it is now possible to correct the increased sensitivity of the skin to sunlight often activated by the retinoid.
Cosmetic and dermatological or pharmaceutical preparations are generally based on a carrier consisting of at least one oil phase. However, only water-based preparations are also possible. Accordingly, oily, creamy, paste, stick-shaped foams or fat-free gels or preferably emulsions are suitable.
Suitable emulsions are O / W emulsions, W / O emulsions, microemulsions or multiple emulsions such as O / W / 0 emulsions or W / O / W emulsions with one or more retinoids according to the present invention in dispersed form, where the emulsions can be obtained, for example, by the phase inversion technique, as described in DE-A-197 26 121.
Customary cosmetic auxiliaries which may be suitable as additives for cosmetic or pharmaceutical preparations are, for example, coemulsifiers, fats and waxes, stabilizers, thickeners, biogenic active ingredients, film formers, perfumes, dyes, release agents, preservatives, pigments, electrolytes (for example magnesium sulfate and pH regulators) The suitable coemulsifiers are preferably the W / 0 and also O / W emulsifiers known, such as, for example, polyglycerol esters, sorbitan esters or partially esterified glycerides. of the fats are glycerides, the waxes which may be mentioned are, inter alia, beeswax, paraffin wax or microcrystalline waxes, if appropriate in combination with hydrophilic waxes.The stabilizers used may be metal salts of fatty acids such as stearate magnesium, aluminum stearate and / or zinc stearate. Suitable thickeners are, for example, crosslinked polyacrylic acids and derivatives thereof, polysaccharides, in particular xanthan gum, guar gum, agar agar, alginates and tyloses, carboxymethylcellulose and hydroxyethylcellulose, also fatty alcohols, monoglycerides and fatty acids, polyacrylates, polyvinyl alcohol and polyvinyl pyrrolidone. Biogenic active ingredients are, for example, plant extracts, protein hydrolysates and vitamin complexes. Typical film formers are, for example, hydrocolloids such as chitosan, microcrystalline chitosan or quaternized chitosan, polyvinyl pyrrolidone, vinyl pyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives and the like. Suitable preservatives are, for example, solution of formaldehyde, P-hydroxybenzoate or sorbic acid. Suitable release agents are, for example, glyceryl esters of distillers such as ethylene glycol distearate, but also fatty acids and monoglycol esters of fatty acids. The colorants that can be used are the substances approved and suitable for cosmetic use, as enlisted for example in the publication "Kosmetische Fárbemittel" [cosmetic dyes] of the Farbstoffkommission der Deutschen
Forschungsgemneinschaft [Bleaching Commission of the German Research Society], published by Verlag, Chemi, Weinheim, 1984. These dyes are commonly used in a concentration from 0.001 to 0.1% by weight, based on the total mixture.
In many cases the use of other antioxidants is advantageous. Thus, in addition to the antioxidants according to the invention specified at the outset, it is possible to use all antioxidants that are customary or suitable for cosmetic and / or dermatological applications.
Antioxidants are advantageously chosen from the group consisting of amino acids (for example glycine, histidine, tyrosine, tryptophan) and derivatives thereof, imidazoles, (for example urocanic acid) and derivatives thereof, peptides such as D, L-carnocin, D -carnocin, L-carnocin and derivatives thereof (for example anserine), carotenoids, carotenes (for example β-carotene, lycopene), and derivatives thereof, chlorophenic acid and derivatives thereof, lipoic acid and derivatives thereof (for example dihydrolipic acid), aurothioglucose, propylthiouracil, and other thiols (eg, thiorodoxin, glutathione, cystine, cystamine, and glucosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl, and lauryl, palmitoyl, oleyl,? -linoleyl, cholesteryl and glyceryl esters) of these) and also the salts of these, dilaurylthio dipropionate, distearyl thiodipropionate, thiodiopropionic acid and derivatives thereof (esters, ethers, peptides, nucleotide lipids, nucleosides and their salts), and compound s sulphoximine (for example butionine sulphoximines, homocysteine sulphoximines, butionine sulfonates, pentahexa-, heptatinine sulphoximine) in very low tolerated doses (for example pool to amol / kg), also chelating agents (metal) (for example α-hydroxy-fatty acids) , palmitic acid, phytic acid, lactoferrin), α-hydroxy acid (eg citric acid, lactic acid, maleic acid), humic acid, bile acid, bile extracts, bilirubin, biliverdin, EDTA and derivatives thereof, fatty acids unsaturated and derivatives thereof (for example α-linolenic acid, linolic acid, oleic acid), folic acid and its derivatives, and corniphenyl benzoate of the benzoin resin, rutinic acid and derivatives thereof, α-glycosylrutine, ferulic acid, furfurilidenglucitol, carnocin, nordihydroguaiácico acid, nordihidroguarético acid, trihidroxibutirofenona, úrico acid and derivatives of this, mannose and its derivatives, zinc and its derivatives (for example ZnO, ZnS? 4), selenium and its derivatives (for example selenomethionine), stilbenes and their derivatives (stilbene oxide, trans-stilbene oxide).
The total amount of the aforementioned antioxidants (one or more compounds) in the preparations is preferably 0.075 to 30% by weight, with particular preference 0.01 to 20% by weight, in particular 0.55 to 10% by weight, based on the weight total of the preparation.
Oily compounds customary in cosmetics are, for example, paraffin oil, glyceryl stearate, isopropyl myristate, diispropyl adipate, cetilestearyl 2-ethylhexanoate, hydrogenated polyisobutene, petrolatum, caprylic / capric triglycerides, microcrystalline wax, lanolin and stearic acid. .
Method of production:
There are various ways to produce cosmetic preparations. For example, the hot / hot method, the hot / cold method or the cold / cold method, as described for example in "Kos etic-Entwicklung, Herstellung an Anwendung kosmetischer Mittel" [Cosmetics-development, production and use of cosmetic compositions ], Wilfried U bach, Thie e Verlag, 1995, page 511. With the help of these methods it is possible to prepare oil-in-water (O / W), water-in-oil (W / O) emulsions, but also multiple emulsions and gels in creams The active ingredients are preferably incorporated after the formulation has been cooled to below 40 ° C, in particularly sensitive cases, preferably after it has cooled to room temperature. For the investigations forming the basis of this invention, an O / W emulsion was prepared in the hot / hot method and then the active ingredients were incorporated into the finished formulation at room temperature.
The formulation used was: Phase A? Ingredient INCI 2.00 Cremophor A 6 Cetearet-6, cetearyl alcohol 2.00 Cremophor A 25 Cetearet 25 3.00 Jojoba oil Simensia seed Chinensis (jojoba)
Oil 3.00 Cetylstearyl alcohol Cetearyl alcohol 10.00 Paraffin oil, Viscous mineral oil 5.00 Petroleum jelly 4.00 Miglyol 812 Caprylic / capric triglyceride 0.10 BHT BHT Phase B 5.00 1, 2-tropylene glycol USP Propylene glycol 0.10 EDTA BD EDTA disodium 20.00 Carbopol 934, 1% in water Demineralized carbomer 0.30 Chemag 2000 Demineralized water and 100 Demineralized water Phase C 0.80 Sodium hydroxide 10% sodium hydroxide in demineralised water Phase D 0.50 Vitamin E acetate Tocopheryl acetate 0.20 Phenoxyethanol phenoxyethanol q. s. Perfume oil
Production:
Phases A and B were separately heated to approximately 80 ° C, phase B was added with stirring to phase A and homogenized. The mixture was neutralized with phase C and then homogenized. With stirring, the cream was cooled to about 40 ° C, phase D was added with stirring and the mixture was homogenized again.
The water-soluble and oil-soluble antioxidants and also the UV filters were then, after cooling the cream at room temperature, incorporated in the finished emulsion. For this, DL-alpha-tocopherol and the UV filter were first added, after the ascorbic acid or sodium ascorbate and subsequently retinol (retinol 15D®, BASF, 15% solution of retinol in a medium chain triglyceride) were added. they incorporated with agitation.
The cream was then packed in aluminum tubes with an internal protective coating or in light-permeable glass containers.
According to the production method described above, creams with different amounts of retinol, (all-rae) a-tocopherol and L-ascorbic and at least the UV filter were produced and stored during
12 weeks at 40 ° C for the stability study.
The subject of the invention was shown in greater detail with reference to the following formulations examples:
Example 1 Skin lotion (O / W emulsion)% by weight
Cetearet 6 and stearyl alcohol 2.50
Cetearet 25 2.50
Hydrogenated cocoglyceride 1.50
PEG-40 dodecylglycol copolymer 3.00
Dimethicone 3.00
Fenetildimethicone 2.00
Cyclomethicone 1.00
Cetearyl octanetoate 5.00
Avocado oil 1.00
Almond oil 2.00
Wheat germ oil 0.80
Pantenol USP 1.00
Fitantriol 0.20
Vitamin E acetate 0.30
Propylene glycol 5.00
Perfume c.s. Preserver c.s. Ascorbate sodium 0.20
Retinol 14D® 0.20
Tocopherol 0.10 Diethylamino hydroxybenzoyl hexyl benzoate 0.06 (Uvinul® A plus) Water c b 100 Example 2 Hand cream (W / O emulsion)% by weight
Cetearyl alcohol 1.00
Glyceryl stearate 1.50
Stearyl alcohol 1.50
Paxil of cetilo 2.00
Vitamin E acetate 0.50
Dimethicone 8.00
Cetearet 6 and stearyl alcohol 3.00
Octyl methoxycinnamate 5.00
Propylene glycol 8.00
Pantenol 1.00
Primal oil 3.00
PEG-7 hydrogenated castor oil 6.00
Glyceryl Oleate 1.00
Fenetildimethicone 3.00
Beeswax 1.50
Carob seed 0.80
Silk powder 0.80
Preserver c.s. Perfume c.s. Borax 0.10
Sodium ascorbate 0.30
Tocopherol 0.60
Retinol 15D® 0.66
Benzophenone-2 (Uvinul® D50) 0.05
Water c b 100 Example 3 Lotion sunscreen (emulsion W / O)% by weight
PEG-7 hydrogenated castor oil 6.00
PEG-40 hydrogenated castor oil 00.50
Palmitado of isopropilo 7.00
Copolymer PEG-45 / dodecylglycol 2.00
Jojoba oil 3.00
Magnesium stearate 0.60
Octyl methoxycinnamate 5.00
C12-C15 alkyl benzoate 5.00
Titanium dioxide 4.00
Propylene glycol 5.00
EDTA 0.20
Preserver c.s. Retinol 15D® 0.33
Water c b 100
Ascorbyl sodium phosphate 1.00
Vitamin E acetate 0.50
Ascorbate sodium 0.20
Tocoferol 1.0Q
Perfume c.s.
Example 4 Multiple emulsion (emulsion W / O / W)% by weight
Paraffin oil 7.50
Cetearyl octanetoate 2.50
Aluminum stearate 0.25
Magnesium stearate 0.25
Microcrystalline wax H 0.50
Cetearyl alcohol 1.00
1.50 lanolin alcohol
Wool wax ointment 1.50
PEG-7 hydrogenated castor oil 0.75
PEG-45 dodecylglycol copolymer 2.00
Cetearet 6 and cetearyl alcohol 2.00
Cetearet 25 1.00
Trilauret 4 phosphate 7.50
Hydroxyethylcellulose 0.20
Propylene glycol 7.50
Magnesium sulfate 0.25
Sodium ascorbate 0.30
Tocoferol 0.01
Retinol 15D® 0.40
Diethylamino hydroxybenzoyl hexyl benzoate 0.06 (Uvinul® A Plus) Water c b 100 Example 5 Microemulsion% by weight
Cetearet 25 13.00
PEG-7 glyceryl cocoate 20.00
Octyldodecanol 5.00
Preserver c.s. Sodium ascorbate 0.10
Tocopherol 0.10
Retino 15D® 0.66
Benzophenone-4 (Uvinul® M 40) 0.07
Water c b 100
Example 6 Liposome gel (hydrophilic gel)% by weight
PEG-40 hydrogenated castor oil 1.00
Bisabolol rae. 0.10
Propylene glycol 8.00
Pantenol 0.50
Water Vitamin E acetate Polysorbate 80 and 3.00 caprylic / capric triglyceride and lecithin Preserver c.s. Perfume c.s. Carbonero 0.50
Sodium ascorbate 0.15
Tocopherol 0.15
Triethanolamine 0.70
Retino 15D® 0.33
Diethylamino hydroxybenzyl hexylbenzoate 0.06
(Uvinul® A PLus) Water c b 100 Example 7 Make-up (cosmetic for decoration)
% in weigh
Cetearet 6 and stearyl alcohol 9.00
Dimeticone 5.00
Cetearyl octaneate 8.00
Macadamia nut oil 5.00
Propylene glycol retinol 15D® 0.66
Water c b 100
Sicovit White E 171 8.00
Sicomet Brown 70 13E 3717 2.00
Ascorbate sodium 0.20
Tocopherol 0.50
Perfume c.s. Benzophenone-3 (Uvinul® M 40) 5.00
Example 8 Liquid makeup (cosmetic for decoration)
% in weigh
Cetearet 6 and stearyl alcohol 7.00
Cetearet 25 5.00
Dimeticone 5.00
Cetearyl octaneate 8.00
Macadamia nut oil 5.00
Propylene glycol 5.00
Retinol 15D® 0.33
Water c b 100
Sicovit White E 171 8.00
Sicomet Brown 70 13E 3717 1.00
Sodium ascorbate 0.10
Tocoferol 0.01
Perfume c.s. Benzophenone-3 (Uvinul® M 40) 5.00
Example 9 Sunscreen lotion (O / W emulsion)% by weight
Cetearet 6 and stearyl alcohol 2.30
Cetearet 25 1.00
Cetyl stearyl alcohol 4.80
Cetilestearyl Octanoate 10.0
Glyceryl monostearate 3.00
Vaseline 3.00
Pantenol USP 1.00
EDTA disodium 0.20
Imidazolidinylurea 0.30
Propylene glycol 5.00
Ascorbyl 2-sodium monofofato 0.20
Vitamin E acetate 1.00
Bisabolol 0.10
Retinol 0.05
Tocopherol 0.20
Ascorbate sodium 0.20
Diethylamino hydrosxybenzoyl benzoate 2.00 (Uvinul® A Plus) ethylhexyl p-methoxycinnamate (Uvinul® MC 80) 3.00
Water c b 100
Claims (12)
- A preparation that contains: a. at least one retinoid, b. at least one water-soluble antioxidant, c. at least one oil soluble antioxidant and d. 0.01 to 10% by weight of at least one UV filter. wherein, during the preparation, by weight part of retinoid there is present at least one part by weight of one or more water-soluble antioxidants and 0.1 to 100 parts by weight of one or more oil-soluble antioxidants, wherein the content of one or more water-soluble antioxidants is in the range from 0.05 to 0.8% by weight, based on the total amount of the preparation.
- 2. The preparation according to claim 1, which is a cosmetic or pharmaceutical preparation.
- 3. The preparation according to one of claims 1 and 2, containing, by weight part of the retinoid, 1 to 6 parts by weight of one or more water-soluble antioxidants and 1 to 10 parts by weight of one or more antioxidants. soluble in oil.
- 4. The preparation according to one of claims 1 and 3, containing, by weight part of the retinoid, 3 to 5 parts by weight of one or more antioxidants soluble in water and 3 to 5 parts by weight of one or more antioxidants. soluble in oil.
- 5. The preparation according to one of claims 1 and 4, which contains, as a water-soluble antioxidant, L-ascorbic acid or salts of L-ascorbic acid.
- 6. The preparation according to one of claims 1 and 5, which contains α-tocopherol as an oil-soluble antioxidant.
- 7. The preparation according to one of claims 1 and 6, wherein the retinoid is all trans retinol.
- 8. The preparation according to claim 7, which contains 0.015 to 0.2% by weight of all trans retinol.
- 9. The preparation according to one of claims 1 to 8, wherein the UV filters are UV-A, UV-B and / or wide-band filters.
- 10. The preparation according to one of claims 1 and 9 in the form of an O / W, W / O or multiple emulsion.
- 11. The preparation according to one of claims 1 to 10, characterized in that it is stored in oxygen-impermeable containers without the addition of protective gas.
- 12. The preparation according to one of claims 1 to 11, characterized in that it is a preparation for the care of the skin.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102004003478.8 | 2004-01-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
MXPA06008185A true MXPA06008185A (en) | 2007-04-10 |
Family
ID=
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