ES2398672T3 - Estabilización de ingredientes activos 5 sensibles al UV - Google Patents
Estabilización de ingredientes activos 5 sensibles al UV Download PDFInfo
- Publication number
- ES2398672T3 ES2398672T3 ES08707930T ES08707930T ES2398672T3 ES 2398672 T3 ES2398672 T3 ES 2398672T3 ES 08707930 T ES08707930 T ES 08707930T ES 08707930 T ES08707930 T ES 08707930T ES 2398672 T3 ES2398672 T3 ES 2398672T3
- Authority
- ES
- Spain
- Prior art keywords
- formula
- merocyanine
- derivatives
- acid
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000004480 active ingredient Substances 0.000 title claims description 23
- 230000006641 stabilisation Effects 0.000 title claims description 7
- 238000011105 stabilization Methods 0.000 title claims description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 125000006735 (C1-C20) heteroalkyl group Chemical group 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 6
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical class [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 claims description 274
- -1 polysiloxane Polymers 0.000 claims description 123
- 239000000203 mixture Substances 0.000 claims description 55
- 150000001875 compounds Chemical class 0.000 claims description 35
- 239000002253 acid Substances 0.000 claims description 34
- 239000006096 absorbing agent Substances 0.000 claims description 23
- 230000000475 sunscreen effect Effects 0.000 claims description 18
- 239000000516 sunscreening agent Substances 0.000 claims description 18
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical class C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 claims description 13
- 229920001296 polysiloxane Polymers 0.000 claims description 13
- 230000005855 radiation Effects 0.000 claims description 12
- 239000004615 ingredient Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical class C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 150000001851 cinnamic acid derivatives Chemical class 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 4
- WMJBVALTYVXGHW-UHFFFAOYSA-N 3,3-diphenylprop-2-enoic acid Chemical class C=1C=CC=CC=1C(=CC(=O)O)C1=CC=CC=C1 WMJBVALTYVXGHW-UHFFFAOYSA-N 0.000 claims description 4
- VMRIVYANZGSGRV-UHFFFAOYSA-N 4-phenyl-2h-triazin-5-one Chemical class OC1=CN=NN=C1C1=CC=CC=C1 VMRIVYANZGSGRV-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 125000001118 alkylidene group Chemical group 0.000 claims description 4
- 150000008366 benzophenones Chemical class 0.000 claims description 4
- 150000001907 coumarones Chemical class 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical class NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 3
- 101100134922 Gallus gallus COR5 gene Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical class COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 claims description 3
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 2
- HIPQTCQUXOFTFI-UHFFFAOYSA-N 2-methoxy-1,3-diphenylpropane-1,3-dione Chemical compound C=1C=CC=CC=1C(=O)C(OC)C(=O)C1=CC=CC=C1 HIPQTCQUXOFTFI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 claims 2
- 150000003872 salicylic acid derivatives Chemical class 0.000 claims 2
- 101100134925 Gallus gallus COR6 gene Chemical group 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 90
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 83
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 60
- 238000002360 preparation method Methods 0.000 description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 50
- 235000019441 ethanol Nutrition 0.000 description 50
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 40
- 235000011187 glycerol Nutrition 0.000 description 39
- 239000003755 preservative agent Substances 0.000 description 38
- HEOCBCNFKCOKBX-RELGSGGGSA-N (1s,2e,4r)-4,7,7-trimethyl-2-[(4-methylphenyl)methylidene]bicyclo[2.2.1]heptan-3-one Chemical compound C1=CC(C)=CC=C1\C=C/1C(=O)[C@]2(C)CC[C@H]\1C2(C)C HEOCBCNFKCOKBX-RELGSGGGSA-N 0.000 description 34
- 229960004697 enzacamene Drugs 0.000 description 34
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 29
- 229920001577 copolymer Polymers 0.000 description 26
- 235000014113 dietary fatty acids Nutrition 0.000 description 26
- 239000000194 fatty acid Substances 0.000 description 26
- 229930195729 fatty acid Natural products 0.000 description 26
- 239000003921 oil Substances 0.000 description 26
- 235000019198 oils Nutrition 0.000 description 26
- 239000004408 titanium dioxide Substances 0.000 description 26
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 26
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 24
- JGUMTYWKIBJSTN-UHFFFAOYSA-N 2-ethylhexyl 4-[[4,6-bis[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 JGUMTYWKIBJSTN-UHFFFAOYSA-N 0.000 description 24
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 24
- DLAHAXOYRFRPFQ-UHFFFAOYSA-N dodecyl benzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=CC=C1 DLAHAXOYRFRPFQ-UHFFFAOYSA-N 0.000 description 24
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 22
- 239000006071 cream Substances 0.000 description 22
- 150000002148 esters Chemical class 0.000 description 22
- BPJZKLBPJBMLQG-KWRJMZDGSA-N propanoyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OC(=O)CC BPJZKLBPJBMLQG-KWRJMZDGSA-N 0.000 description 22
- 239000003795 chemical substances by application Substances 0.000 description 21
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 21
- 239000002304 perfume Substances 0.000 description 21
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 21
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 20
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-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 20
- 239000002537 cosmetic Substances 0.000 description 19
- 239000004205 dimethyl polysiloxane Substances 0.000 description 19
- 239000000975 dye Substances 0.000 description 19
- 239000000839 emulsion Substances 0.000 description 19
- 238000009472 formulation Methods 0.000 description 19
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 19
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 19
- BANXPJUEBPWEOT-UHFFFAOYSA-N 2-methyl-Pentadecane Chemical compound CCCCCCCCCCCCCC(C)C BANXPJUEBPWEOT-UHFFFAOYSA-N 0.000 description 18
- 229920002125 Sokalan® Polymers 0.000 description 18
- XNEFYCZVKIDDMS-UHFFFAOYSA-N avobenzone Chemical compound C1=CC(OC)=CC=C1C(=O)CC(=O)C1=CC=C(C(C)(C)C)C=C1 XNEFYCZVKIDDMS-UHFFFAOYSA-N 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 18
- ZAKOWWREFLAJOT-UHFFFAOYSA-N d-alpha-Tocopheryl acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-UHFFFAOYSA-N 0.000 description 18
- 229940008099 dimethicone Drugs 0.000 description 18
- 239000000126 substance Substances 0.000 description 18
- UVCJGUGAGLDPAA-UHFFFAOYSA-N ensulizole Chemical compound N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 UVCJGUGAGLDPAA-UHFFFAOYSA-N 0.000 description 17
- 229960000655 ensulizole Drugs 0.000 description 17
- 150000004665 fatty acids Chemical class 0.000 description 17
- 229940042585 tocopherol acetate Drugs 0.000 description 17
- 235000021355 Stearic acid Nutrition 0.000 description 16
- 239000006210 lotion Substances 0.000 description 16
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 16
- 239000008117 stearic acid Substances 0.000 description 16
- 229960001631 carbomer Drugs 0.000 description 14
- 229940081733 cetearyl alcohol Drugs 0.000 description 14
- 229920001971 elastomer Polymers 0.000 description 14
- 239000003205 fragrance Substances 0.000 description 14
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- 235000010446 mineral oil Nutrition 0.000 description 13
- 230000002335 preservative effect Effects 0.000 description 13
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 150000001298 alcohols Chemical class 0.000 description 12
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- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 12
- FMJSMJQBSVNSBF-UHFFFAOYSA-N octocrylene Chemical group C=1C=CC=CC=1C(=C(C#N)C(=O)OCC(CC)CCCC)C1=CC=CC=C1 FMJSMJQBSVNSBF-UHFFFAOYSA-N 0.000 description 12
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 8
- 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 8
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- 229940104261 taurate Drugs 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- BORJONZPSTVSFP-UHFFFAOYSA-N tetradecyl 2-hydroxypropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)O BORJONZPSTVSFP-UHFFFAOYSA-N 0.000 description 1
- AVKVDDQTHIQFSC-UHFFFAOYSA-N tetradecyl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCC AVKVDDQTHIQFSC-UHFFFAOYSA-N 0.000 description 1
- DHZWALZKPWZSMA-UHFFFAOYSA-N tetradecyl oleate Natural products CCCCCCCCCCCCCCOC(=O)CCCCCCCC=CCCCCCCCC DHZWALZKPWZSMA-UHFFFAOYSA-N 0.000 description 1
- DZKXJUASMGQEMA-UHFFFAOYSA-N tetradecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC DZKXJUASMGQEMA-UHFFFAOYSA-N 0.000 description 1
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- 125000003831 tetrazolyl group Chemical group 0.000 description 1
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- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229940094937 thioredoxin Drugs 0.000 description 1
- 108060008226 thioredoxin Proteins 0.000 description 1
- 239000010678 thyme oil Substances 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- 239000001585 thymus vulgaris Substances 0.000 description 1
- 125000002640 tocopherol group Chemical class 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- AQWHMKSIVLSRNY-UHFFFAOYSA-N trans-Octadec-5-ensaeure Natural products CCCCCCCCCCCCC=CCCCC(O)=O AQWHMKSIVLSRNY-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-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
- RBNWAMSGVWEHFP-UHFFFAOYSA-N trans-p-Menthane-1,8-diol Chemical compound CC(C)(O)C1CCC(C)(O)CC1 RBNWAMSGVWEHFP-UHFFFAOYSA-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
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- 150000003852 triazoles Chemical class 0.000 description 1
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- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- FQAZRHVERGEKOS-UHFFFAOYSA-N tripropan-2-yl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CC(C)OC(=O)CC(O)(C(=O)OC(C)C)CC(=O)OC(C)C FQAZRHVERGEKOS-UHFFFAOYSA-N 0.000 description 1
- ODHUFJLMXDXVRC-UHFFFAOYSA-N tripropyl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CCCOC(=O)CC(O)(C(=O)OCCC)CC(=O)OCCC ODHUFJLMXDXVRC-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- ZQTYRTSKQFQYPQ-UHFFFAOYSA-N trisiloxane Chemical compound [SiH3]O[SiH2]O[SiH3] ZQTYRTSKQFQYPQ-UHFFFAOYSA-N 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
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- 229940116269 uric acid Drugs 0.000 description 1
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- WXETUDXXEZHSCS-MAVITOTKSA-N vertofix coeur Chemical compound C[C@@H]1CC[C@@]2(C(/CC3)=C\C(C)=O)[C@@H]3C(C)(C)[C@@H]1C2 WXETUDXXEZHSCS-MAVITOTKSA-N 0.000 description 1
- 239000010679 vetiver oil Substances 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
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- 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
- 239000008170 walnut oil Substances 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229940043810 zinc pyrithione Drugs 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 239000011686 zinc sulphate Substances 0.000 description 1
- 235000009529 zinc sulphate Nutrition 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
- A61K8/30—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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives 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
- A61K8/49—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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/004—Aftersun preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/04—Preparations for care of the skin for chemically tanning the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/04—Preparations for permanent waving or straightening the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07101171 | 2007-01-25 | ||
| EP07101171 | 2007-01-25 | ||
| PCT/EP2008/050440 WO2008090066A2 (en) | 2007-01-25 | 2008-01-16 | Stabilization of uv-sensitive active ingredients |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2398672T3 true ES2398672T3 (es) | 2013-03-20 |
Family
ID=38236197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES08707930T Active ES2398672T3 (es) | 2007-01-25 | 2008-01-16 | Estabilización de ingredientes activos 5 sensibles al UV |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8535648B2 (OSRAM) |
| EP (1) | EP2120854B1 (OSRAM) |
| JP (1) | JP5733895B2 (OSRAM) |
| KR (1) | KR101468484B1 (OSRAM) |
| CN (1) | CN101711151B (OSRAM) |
| BR (1) | BRPI0806827B1 (OSRAM) |
| ES (1) | ES2398672T3 (OSRAM) |
| WO (1) | WO2008090066A2 (OSRAM) |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008048328A1 (de) * | 2008-09-16 | 2010-04-15 | Beiersdorf Ag | UV-Filter haltige O/W-Wirkstoffemulsion |
| FR2957251B1 (fr) * | 2010-03-15 | 2012-03-02 | Oreal | Composition contenant une s-triazine siliciee substituee par au moins deux groupes alkylaminobenzoates et un filtre uv merocyanine hydrophile ou hydrosoluble |
| CN102933195B (zh) * | 2010-03-15 | 2015-04-01 | 莱雅公司 | 包含二苯甲酰基甲烷掩蔽剂和部花青二氰基或氰基乙酸酯衍生物的组合物;用于二苯甲酰基甲烷掩蔽剂的光稳定化的方法 |
| FR2967900B1 (fr) * | 2010-11-25 | 2024-01-05 | Oreal | Composition contenant un filtre dibenzoylmethane et un filtre uv merocyanine hydrophile ou hydrosoluble ; procede de photostabilisation du filtre dibenzoylmethane |
| BR112012023232B1 (pt) * | 2010-03-15 | 2021-03-23 | L'oreal | Composição, processo para melhorar a estabilidade química em relação à radiação uv e compostos de merocianina |
| FR2957249B1 (fr) * | 2010-03-15 | 2022-12-02 | Oreal | Composition contenant un filtre dibenzoylmethane et un derive dicyano ou cyanoacetate de merocyanine ; procede de photostabilisation du filtre dibenzoylmethane |
| US8747817B1 (en) | 2010-12-02 | 2014-06-10 | William Scott Prendergast | System and method of complementary day/night children's skin cream compositions |
| US20130309185A1 (en) * | 2010-12-10 | 2013-11-21 | Hani M. Fares | Compositions comprising stabilized keto- enol uv absorbers |
| WO2013010590A1 (en) * | 2011-07-21 | 2013-01-24 | L'oreal | Cosmetic and/or dermatological composition containing a merocyanine derivative comprising specific polar groups consisting of hydroxyl- and ether-functionalities |
| WO2013114004A1 (fr) * | 2012-01-31 | 2013-08-08 | Pierre Fabre Dermo-Cosmetique | Composition et association de filtres solaires photostabilisatrices de bmdbm |
| WO2014050369A1 (ja) * | 2012-09-25 | 2014-04-03 | Dic株式会社 | 粘着テープ及び粘着テープの製造方法 |
| FR3001137B1 (fr) * | 2013-01-21 | 2015-02-27 | Oreal | Emulsion eau-dans-huile cosmetique ou dermatologique comprenant une merocyanine et au moins un polymere emulsionnant du type ester d'acide gras et de glycol polyoxyalkylene |
| FR3001132B1 (fr) * | 2013-01-21 | 2015-05-29 | Oreal | Composition cosmetique ou dermatologique comprenant une merocyanine et un compose 2-hydroxybenzophenone aminosubstitue |
| FR3001134B1 (fr) * | 2013-01-21 | 2015-06-19 | Oreal | Composition cosmetique ou dermatologique comprenant une merocyanine et un compose bis-resorcinyl triazine |
| FR3001136B1 (fr) | 2013-01-21 | 2015-06-19 | Oreal | Emulsion cosmetique ou dermatologique comprenant une merocyanine et un systeme emulsionnant contenant un polymere amphiphile comportant au moins un motif acide acrylamido 2-methylpropane sulfonique |
| FR3001129B1 (fr) * | 2013-01-21 | 2015-06-19 | Oreal | Composition cosmetique ou dermatologique comprenant une merocyanine et un filtre uv benzotriazole lipophile |
| CN105431130B (zh) * | 2013-01-21 | 2018-11-09 | 莱雅公司 | 包含部花青、有机uvb-遮蔽剂和附加的有机uva-遮蔽剂的化妆品或者皮肤病学组合物 |
| WO2014111563A2 (en) | 2013-01-21 | 2014-07-24 | L'oreal | Cosmetic or dermatological composition comprising a merocyanine and a lipophilic benzotriazole uv-screening agent and/or a bis-resorcinyl triazine compound |
| JP6487337B2 (ja) * | 2013-01-21 | 2019-03-20 | ロレアル | メロシアニンと不溶性有機ｕｖ遮蔽剤及び／又は不溶性無機ｕｖ遮蔽剤とを含む化粧用又は皮膚用組成物 |
| FR3001139B1 (fr) * | 2013-01-21 | 2015-06-19 | Oreal | Composition cosmetique ou dermatologique comprenant une merocyanine, un filtre uvb organique lipophile liquide et un filtre uva organique additionnel |
| FR3001133B1 (fr) | 2013-01-21 | 2015-03-20 | Oreal | Composition cosmetique ou dermatologique comprenant une merocyanine et une phase huileuse comprenant au moins un compose amide particulier |
| FR3001130B1 (fr) * | 2013-01-21 | 2015-06-19 | Oreal | Composition cosmetique ou dermatologique comprenant une merocyanine et un filtre uv organique insoluble |
| FR3001216B1 (fr) | 2013-01-21 | 2015-02-27 | Oreal | Composition cosmetique ou dermatologique comprenant une merocyanine, une phase huileuse et un mono-alcanol en c1-c4 |
| FR3001140B1 (fr) * | 2013-01-21 | 2015-06-19 | Oreal | Composition cosmetique ou dermatologique comprenant une merocyanine, un filtre uvb organique hydrophile et un filtre uva organique additionnel |
| WO2014111567A2 (en) | 2013-01-21 | 2014-07-24 | L'oreal | Cosmetic or dermatological composition comprising a merocyanine and a uva-screening agent of the amino-substituted 2-hydroxybenzophenone type and/or a hydrophilic organic uva-screening agent |
| FR3001138B1 (fr) * | 2013-01-21 | 2015-06-19 | Oreal | Composition anhydre cosmetique ou dermatologique comprenant une merocyanine et une phase huileuse |
| FR3001128B1 (fr) * | 2013-01-21 | 2015-06-19 | Oreal | Emulsion cosmetique ou dermatologique comprenant une merocyanine et un systeme emulsionnant contenant un sel de metal alcalin d'ester d'acide phosphorique et d'alcool gras |
| FR3001131B1 (fr) * | 2013-01-21 | 2015-06-19 | Oreal | Emulsion cosmetique ou dermatologique comprenant une merocyanine et un systeme emulsionnant contenant un tensioactif gemine. |
| DE102013213170A1 (de) * | 2013-07-04 | 2015-01-08 | Beiersdorf Ag | Octocrylenfreies, geruchsstabiles Sonnenschutzmittel |
| KR102100244B1 (ko) | 2013-12-19 | 2020-04-13 | 에스케이이노베이션 주식회사 | 리튬 이차전지 전해액 및 이를 포함하는 리튬 이차전지 |
| PL3122321T3 (pl) | 2014-03-27 | 2021-07-12 | Kancor Ingredients Ltd | Fotostabilna kompozycja przeciwsłoneczna do stosowania miejscowego |
| US20170304658A1 (en) | 2014-08-28 | 2017-10-26 | L'oreal | Gel/gel composition comprising a uv-screening agent |
| BR112017010702A2 (pt) | 2014-11-24 | 2018-02-14 | Oreal | composição, uso de um filossilicato sintético, uso cosmético de uma composição, processo de tratamento cosmético, processo cosmético |
| FR3033249B1 (fr) * | 2015-03-06 | 2020-11-13 | Developpement Industrialisation Et Promotion De Tech Avancees | Composition cosmetique solaire aqueuse depourvue de tensioactifs |
| FR3037243B1 (fr) | 2015-06-11 | 2018-11-16 | L'oreal | Composition comprenant un filtre uv, un polymere hydrophile reticule anionique, un tensioactif ayant une hlb inferieure ou egale a 5 et un copolymere silicone |
| JP6847057B2 (ja) | 2015-06-19 | 2021-03-24 | ロレアル | 高レベルの脂溶性ｕｖフィルターを含有する日焼け止め組成物 |
| FR3046928B1 (fr) | 2016-01-26 | 2019-08-09 | L'oreal | Composition cosmetique ou dermatologique comprenant une merocyanine et une phase huileuse comprenant au moins un amide n-substitue |
| US10485745B2 (en) | 2016-04-29 | 2019-11-26 | L'oreal | UV-A/UV-B sunscreen composition |
| FR3060361B1 (fr) | 2016-12-21 | 2018-12-07 | L'oreal | Emulsion eau-dans-huile comprenant un systeme emulsionnant particulier, une argile lipophile, une poudre d’organopolysiloxane elastomerique enrobee d’une resine de silicone |
| FR3060355B1 (fr) | 2016-12-21 | 2020-01-24 | L'oreal | Emulsion eau-dans-huile contenant la baicaline, une base xanthique, une vitamine b3 et un sel de cation metallique multivalent |
| FR3060997B1 (fr) | 2016-12-23 | 2019-05-31 | L'oreal | Composition comprenant de la baicaline |
| FR3073402B1 (fr) | 2017-11-15 | 2020-05-15 | L'oreal | Composition comprenant de la baicaline et/ou l’un de ses derives et un polymere acrylique particulier |
| FR3073400B1 (fr) | 2017-11-15 | 2024-08-09 | Oreal | Emulsion cosmetique contenant un tensioactif gemine et un polymere lipophile |
| US10813875B2 (en) | 2018-04-23 | 2020-10-27 | L'oreal | Memory shape sunscreen composition |
| FR3090329B1 (fr) | 2018-12-21 | 2020-12-04 | Oreal | Composition comprenant un filtre UV, un polymère hydrophile réticulé anionique, un tensioactif ayant une HLB inférieure ou égale à 5 et un alcane non volatil |
| FR3103704B1 (fr) | 2019-11-29 | 2022-07-08 | Oreal | Composition comprenant un filtre UV, un polymère éthylénique à groupe acide phosphonique et une huile hydrocarbonée |
| FR3103705B1 (fr) | 2019-11-29 | 2021-12-17 | Oreal | Composition comprenant un filtre UV, un polymère séquencé à groupe acide phosphonique et une huile hydrocarbonée |
| FR3104976B1 (fr) | 2019-12-20 | 2021-12-24 | Oreal | Composition à base de rétinol |
| FR3104975B1 (fr) | 2019-12-20 | 2021-12-17 | Oreal | Composition à base de rétinol |
| FR3111074B1 (fr) | 2020-06-08 | 2022-07-01 | Oreal | Composition à base de rétinol |
| FR3111075B1 (fr) | 2020-06-08 | 2022-12-16 | Oreal | Composition à base de rétinol |
| FR3115991B1 (fr) | 2020-11-06 | 2023-11-03 | Oreal | Composition anhydre solide comprenant un filtre UV organique lipophile, une huile hydrocarbonée, et au moins 10 % d’une cire à haut point de fusion |
| FR3142344A1 (fr) | 2022-11-30 | 2024-05-31 | L'oreal | Composition à base de rétinol |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08239509A (ja) * | 1995-03-06 | 1996-09-17 | Fuji Photo Film Co Ltd | ポリマーフィルム |
| WO2000020388A1 (de) * | 1998-10-02 | 2000-04-13 | Ciba Specialty Chemicals Holding Inc. | Indolinderivate als lichtschutzmittel |
| DK1549283T3 (da) * | 2002-07-10 | 2013-01-02 | Basf Se | Merocyanine derivatives for cosmetic use |
| WO2004075871A1 (en) * | 2003-02-26 | 2004-09-10 | Fuji Photo Film B.V. | Cosmetic uv-screen compositions and aminobutadiene-based uv-absorbing complexes therefor |
| GB2416351A (en) * | 2004-06-29 | 2006-01-25 | Ciba Sc Holding Ag | Use of myocyanine derivatives for the protection of human hair and skin from UV radiation |
| WO2006016806A1 (en) * | 2004-08-11 | 2006-02-16 | Fujifilm Manufacturing Europe B.V. | Aminobutadiene-based uv screens |
| JP5001154B2 (ja) | 2004-09-20 | 2012-08-15 | ロレアル | シランメロシアニンスルホン誘導体；シランメロシアニンスルホン誘導体を含有する光保護用組成物；それらのｕｖフィルターとしての使用 |
| FR2886144B1 (fr) * | 2005-05-27 | 2007-06-29 | Oreal | Procede de photostabilisation d'un derive de dibenzoylmethane par un derive sulfone de merocyanine ; compositions cosmetiques photoprotectrices contenant cette associaton. |
| EP1893697B1 (en) * | 2005-06-23 | 2014-04-23 | Basf Se | Nitrosulfide dyes |
| AU2006274968B2 (en) * | 2005-07-29 | 2012-02-23 | Basf Se | Stabilization of body-care and household products against degradation by UV radiation using merocyanine derivatives |
| CN101277674B (zh) * | 2005-07-29 | 2013-01-16 | 西巴特殊化学制品控股公司 | 使用部花青衍生物使身体护理产品和家用产品稳定化防止uv辐射引起的降解 |
| US7789916B2 (en) * | 2005-10-06 | 2010-09-07 | Ciba Corporation | Triarylmethane dyes |
| JP5558715B2 (ja) * | 2005-10-06 | 2014-07-23 | チバ ホールディング インコーポレーテッド | チオール染料 |
| EP1937780B1 (en) * | 2005-10-11 | 2013-02-13 | Basf Se | Mixture of sulfide dyes |
-
2008
- 2008-01-16 CN CN200880001444XA patent/CN101711151B/zh active Active
- 2008-01-16 JP JP2009546715A patent/JP5733895B2/ja active Active
- 2008-01-16 WO PCT/EP2008/050440 patent/WO2008090066A2/en not_active Ceased
- 2008-01-16 US US12/520,880 patent/US8535648B2/en active Active
- 2008-01-16 KR KR1020097013096A patent/KR101468484B1/ko active Active
- 2008-01-16 EP EP08707930A patent/EP2120854B1/en active Active
- 2008-01-16 BR BRPI0806827A patent/BRPI0806827B1/pt active IP Right Grant
- 2008-01-16 ES ES08707930T patent/ES2398672T3/es active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN101711151B (zh) | 2013-12-18 |
| CN101711151A (zh) | 2010-05-19 |
| BRPI0806827A2 (pt) | 2011-09-13 |
| EP2120854A2 (en) | 2009-11-25 |
| KR101468484B1 (ko) | 2014-12-04 |
| JP2010516725A (ja) | 2010-05-20 |
| JP5733895B2 (ja) | 2015-06-10 |
| EP2120854B1 (en) | 2012-12-26 |
| US8535648B2 (en) | 2013-09-17 |
| US20100104523A1 (en) | 2010-04-29 |
| BRPI0806827B1 (pt) | 2016-11-29 |
| WO2008090066A3 (en) | 2008-09-12 |
| KR20090104005A (ko) | 2009-10-05 |
| WO2008090066A2 (en) | 2008-07-31 |
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