HUE025422T2 - Szilil polimer benzoesav-észter vegyületek, alkalmazásuk és az azokat tartalmazó készítmények - Google Patents
Szilil polimer benzoesav-észter vegyületek, alkalmazásuk és az azokat tartalmazó készítmények Download PDFInfo
- Publication number
- HUE025422T2 HUE025422T2 HUE10765444A HUE10765444A HUE025422T2 HU E025422 T2 HUE025422 T2 HU E025422T2 HU E10765444 A HUE10765444 A HU E10765444A HU E10765444 A HUE10765444 A HU E10765444A HU E025422 T2 HUE025422 T2 HU E025422T2
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- HU
- Hungary
- Prior art keywords
- branched
- straight
- alkyl
- cycloalkyl
- ppm
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 120
- -1 benzoic acid ester compounds Chemical class 0.000 title claims description 45
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title description 14
- 239000005711 Benzoic acid Substances 0.000 title description 5
- 235000010233 benzoic acid Nutrition 0.000 title description 5
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 title description 2
- 239000002537 cosmetic Substances 0.000 claims abstract description 34
- 238000002360 preparation method Methods 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 29
- 230000005855 radiation Effects 0.000 claims abstract description 19
- 230000008569 process Effects 0.000 claims abstract description 18
- 241001465754 Metazoa Species 0.000 claims abstract description 16
- 229920001558 organosilicon polymer Polymers 0.000 claims abstract description 4
- 230000009021 linear effect Effects 0.000 claims description 184
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 88
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 62
- 150000001875 compounds Chemical class 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 229920000642 polymer Polymers 0.000 claims description 50
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 44
- 239000000516 sunscreening agent Substances 0.000 claims description 35
- 230000000475 sunscreen effect Effects 0.000 claims description 34
- 230000003711 photoprotective effect Effects 0.000 claims description 32
- 239000000178 monomer Substances 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 230000000750 progressive effect Effects 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 22
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 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 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims description 9
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 claims description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
- 229960005193 avobenzone Drugs 0.000 claims description 8
- 239000002243 precursor Substances 0.000 claims description 8
- 239000006096 absorbing agent Substances 0.000 claims description 7
- 239000002105 nanoparticle Substances 0.000 claims description 7
- YDIYEOMDOWUDTJ-UHFFFAOYSA-N 4-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=C(C(O)=O)C=C1 YDIYEOMDOWUDTJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000011859 microparticle Substances 0.000 claims description 6
- LALVCWMSKLEQMK-UHFFFAOYSA-N 1-phenyl-3-(4-propan-2-ylphenyl)propane-1,3-dione Chemical compound C1=CC(C(C)C)=CC=C1C(=O)CC(=O)C1=CC=CC=C1 LALVCWMSKLEQMK-UHFFFAOYSA-N 0.000 claims description 5
- MEZZCSHVIGVWFI-UHFFFAOYSA-N 2,2'-Dihydroxy-4-methoxybenzophenone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1O MEZZCSHVIGVWFI-UHFFFAOYSA-N 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229960004960 dioxybenzone Drugs 0.000 claims description 5
- CBZHHQOZZQEZNJ-UHFFFAOYSA-N ethyl 4-[bis(2-hydroxypropyl)amino]benzoate Chemical compound CCOC(=O)C1=CC=C(N(CC(C)O)CC(C)O)C=C1 CBZHHQOZZQEZNJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 125000005270 trialkylamine group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- 230000001681 protective effect Effects 0.000 claims 3
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical group O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 2
- 229910021556 Chromium(III) chloride Inorganic materials 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical class O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 claims 1
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 claims 1
- 239000011636 chromium(III) chloride Substances 0.000 claims 1
- 235000007831 chromium(III) chloride Nutrition 0.000 claims 1
- 125000005265 dialkylamine group Chemical group 0.000 claims 1
- 125000003963 dichloro group Chemical group Cl* 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 claims 1
- 229960005181 morphine Drugs 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims 1
- RLZZZVKAURTHCP-UHFFFAOYSA-N phenanthrene-3,4-diol Chemical compound C1=CC=C2C3=C(O)C(O)=CC=C3C=CC2=C1 RLZZZVKAURTHCP-UHFFFAOYSA-N 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 125000005936 piperidyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 229960004889 salicylic acid Drugs 0.000 claims 1
- 239000002245 particle Substances 0.000 abstract description 55
- 150000001558 benzoic acid derivatives Chemical class 0.000 abstract description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 128
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 32
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 239000012071 phase Substances 0.000 description 24
- 239000002904 solvent Substances 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000004128 high performance liquid chromatography Methods 0.000 description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 14
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000004615 ingredient Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 230000006750 UV protection Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 125000000565 sulfonamide group Chemical group 0.000 description 8
- TUWAHNRMLXYPCH-UHFFFAOYSA-N [4-(3-triethoxysilylpropoxymethyl)phenyl] benzoate Chemical compound C1=CC(COCCC[Si](OCC)(OCC)OCC)=CC=C1OC(=O)C1=CC=CC=C1 TUWAHNRMLXYPCH-UHFFFAOYSA-N 0.000 description 7
- URFQUMAEMXIRSH-UHFFFAOYSA-N [4-(3-triethoxysilylpropylcarbamoyloxymethyl)phenyl] benzoate Chemical compound C1=CC(COC(=O)NCCC[Si](OCC)(OCC)OCC)=CC=C1OC(=O)C1=CC=CC=C1 URFQUMAEMXIRSH-UHFFFAOYSA-N 0.000 description 7
- CKOOABJZYWLHMN-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1.C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 CKOOABJZYWLHMN-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 230000004224 protection Effects 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- SEYOWWRWMHDHPD-UHFFFAOYSA-N (3-aminophenyl) benzoate Chemical compound NC1=CC=CC(OC(=O)C=2C=CC=CC=2)=C1 SEYOWWRWMHDHPD-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- LDGPGECNTRBRHA-UHFFFAOYSA-N [4-(3-triethoxysilylpropoxy)phenyl] benzoate Chemical compound C1=CC(OCCC[Si](OCC)(OCC)OCC)=CC=C1OC(=O)C1=CC=CC=C1 LDGPGECNTRBRHA-UHFFFAOYSA-N 0.000 description 6
- JHNKOPFWIDVNSD-UHFFFAOYSA-N [4-(3-triethoxysilylpropylcarbamoylamino)phenyl] benzoate Chemical compound C1=CC(NC(=O)NCCC[Si](OCC)(OCC)OCC)=CC=C1OC(=O)C1=CC=CC=C1 JHNKOPFWIDVNSD-UHFFFAOYSA-N 0.000 description 6
- FMNSYEOMCBSTQR-UHFFFAOYSA-N [4-(3-triethoxysilylpropylcarbamoyloxy)phenyl] benzoate Chemical compound C1=CC(OC(=O)NCCC[Si](OCC)(OCC)OCC)=CC=C1OC(=O)C1=CC=CC=C1 FMNSYEOMCBSTQR-UHFFFAOYSA-N 0.000 description 6
- 239000006071 cream Substances 0.000 description 6
- 238000011065 in-situ storage Methods 0.000 description 6
- 239000006210 lotion Substances 0.000 description 6
- 229960001173 oxybenzone Drugs 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- WHQOKFZWSDOTQP-UHFFFAOYSA-N 2,3-dihydroxypropyl 4-aminobenzoate Chemical compound NC1=CC=C(C(=O)OCC(O)CO)C=C1 WHQOKFZWSDOTQP-UHFFFAOYSA-N 0.000 description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 5
- XMRSNXYPQUFCKW-UHFFFAOYSA-N [4-(3-triethoxysilylpropylamino)phenyl] benzoate Chemical compound C1=CC(NCCC[Si](OCC)(OCC)OCC)=CC=C1OC(=O)C1=CC=CC=C1 XMRSNXYPQUFCKW-UHFFFAOYSA-N 0.000 description 5
- FQYHKNWLDQUNBE-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl] benzoate Chemical compound C1=CC(CO)=CC=C1OC(=O)C1=CC=CC=C1 FQYHKNWLDQUNBE-UHFFFAOYSA-N 0.000 description 5
- UVCJGUGAGLDPAA-UHFFFAOYSA-N ensulizole Chemical compound N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 UVCJGUGAGLDPAA-UHFFFAOYSA-N 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 229910000077 silane Inorganic materials 0.000 description 5
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 5
- 229960000368 sulisobenzone Drugs 0.000 description 5
- WSSJONWNBBTCMG-UHFFFAOYSA-N 2-hydroxybenzoic acid (3,3,5-trimethylcyclohexyl) ester Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C1=CC=CC=C1O WSSJONWNBBTCMG-UHFFFAOYSA-N 0.000 description 4
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 description 4
- WYWZRNAHINYAEF-UHFFFAOYSA-N Padimate O Chemical compound CCCCC(CC)COC(=O)C1=CC=C(N(C)C)C=C1 WYWZRNAHINYAEF-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000004904 UV filter Substances 0.000 description 4
- PZEJHCJICPCSMC-UHFFFAOYSA-N [3-(3-triethoxysilylpropoxy)phenyl] benzoate Chemical compound CCO[Si](OCC)(OCC)CCCOC1=CC=CC(OC(=O)C=2C=CC=CC=2)=C1 PZEJHCJICPCSMC-UHFFFAOYSA-N 0.000 description 4
- PEXVVDTXJCUEOZ-UHFFFAOYSA-N [3-(3-triethoxysilylpropylamino)phenyl] benzoate Chemical compound CCO[Si](OCC)(OCC)CCCNC1=CC=CC(OC(=O)C=2C=CC=CC=2)=C1 PEXVVDTXJCUEOZ-UHFFFAOYSA-N 0.000 description 4
- PBAWGEANUOJSPB-UHFFFAOYSA-N [3-(3-triethoxysilylpropylcarbamoylamino)phenyl] benzoate Chemical compound CCO[Si](OCC)(OCC)CCCNC(=O)NC1=CC=CC(OC(=O)C=2C=CC=CC=2)=C1 PBAWGEANUOJSPB-UHFFFAOYSA-N 0.000 description 4
- DHFQNABNBAKHOU-UHFFFAOYSA-N [3-(3-triethoxysilylpropylcarbamoyloxy)phenyl] benzoate Chemical compound CCO[Si](OCC)(OCC)CCCNC(=O)OC1=CC=CC(OC(=O)C=2C=CC=CC=2)=C1 DHFQNABNBAKHOU-UHFFFAOYSA-N 0.000 description 4
- PTNOKROCBHCFRJ-UHFFFAOYSA-N [3-[bis(3-triethoxysilylpropyl)amino]phenyl] benzoate Chemical compound CCO[Si](OCC)(OCC)CCCN(CCC[Si](OCC)(OCC)OCC)C1=CC=CC(OC(=O)C=2C=CC=CC=2)=C1 PTNOKROCBHCFRJ-UHFFFAOYSA-N 0.000 description 4
- NMNIDABZAYPRGG-UHFFFAOYSA-N [4-[bis(3-triethoxysilylpropyl)amino]phenyl] benzoate Chemical compound C1=CC(N(CCC[Si](OCC)(OCC)OCC)CCC[Si](OCC)(OCC)OCC)=CC=C1OC(=O)C1=CC=CC=C1 NMNIDABZAYPRGG-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 229960000846 camphor Drugs 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000004205 dimethyl polysiloxane Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000003094 microcapsule Substances 0.000 description 4
- FMJSMJQBSVNSBF-UHFFFAOYSA-N octocrylene Chemical compound C=1C=CC=CC=1C(=C(C#N)C(=O)OCC(CC)CCCC)C1=CC=CC=C1 FMJSMJQBSVNSBF-UHFFFAOYSA-N 0.000 description 4
- YAGMLECKUBJRNO-UHFFFAOYSA-N octyl 4-(dimethylamino)benzoate Chemical compound CCCCCCCCOC(=O)C1=CC=C(N(C)C)C=C1 YAGMLECKUBJRNO-UHFFFAOYSA-N 0.000 description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 3
- PDHSAQOQVUXZGQ-JKSUJKDBSA-N (2r,3s)-2-(3,4-dihydroxyphenyl)-3-methoxy-3,4-dihydro-2h-chromene-5,7-diol Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2OC)=CC=C(O)C(O)=C1 PDHSAQOQVUXZGQ-JKSUJKDBSA-N 0.000 description 3
- JWLQSDXEKWFFBU-UHFFFAOYSA-N (3-nitrophenyl) benzoate Chemical compound [O-][N+](=O)C1=CC=CC(OC(=O)C=2C=CC=CC=2)=C1 JWLQSDXEKWFFBU-UHFFFAOYSA-N 0.000 description 3
- 208000031968 Cadaver Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- OVXZVDMCQPLHIY-QXGOIDDHSA-L calcium;4-[[(2r)-2,4-dihydroxy-3,3-dimethylbutanoyl]amino]butanoate Chemical compound [Ca+2].OCC(C)(C)[C@@H](O)C(=O)NCCCC([O-])=O.OCC(C)(C)[C@@H](O)C(=O)NCCCC([O-])=O OVXZVDMCQPLHIY-QXGOIDDHSA-L 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 235000013336 milk Nutrition 0.000 description 3
- 210000004080 milk Anatomy 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 3
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 3
- JFAXJRJMFOACBO-UHFFFAOYSA-N (4-hydroxyphenyl) benzoate Chemical compound C1=CC(O)=CC=C1OC(=O)C1=CC=CC=C1 JFAXJRJMFOACBO-UHFFFAOYSA-N 0.000 description 2
- BSWRKKZXYUISNO-UHFFFAOYSA-N 2-(2-ethylhexoxy)benzoic acid Chemical compound CCCCC(CC)COC1=CC=CC=C1C(O)=O BSWRKKZXYUISNO-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
- A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
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- A—HUMAN NECESSITIES
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- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0241—Containing particulates characterized by their shape and/or structure
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- A—HUMAN NECESSITIES
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- 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
- A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
- A61K8/585—Organosilicon compounds
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
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Claims (7)
- Szabadalmi ígértyppntok 1» Eljárás progresszív fütoproiektív organoszliikon polimer elpáilására, amely megában foglalja egy (I) képletü monomer:ahol a képletben; R jelentését az (I), (II), (Ili), és (ív) által alkotott csoportból választjuk:Ri, % R3t Ræ és R§ jelentését egymástól függetlenül az alábbiak áltál alkotott csoportból válaszfük: ff, egyenes vagy elágazó láncú (G-s-Cs)aRsl, (CrGsJ-cIklcatkit, ORe, NH& NNR?, NRaRs, CÖÖH: COOR?0> C0MH2, CONHh, CömnRn, SO2RH2, SO^mu, és SOsRRtsRis; R§ jelentése egyenes vagy elágazó láncé {C-rCejaikiI vagy (Gs-Celeikloalkll; R7 jelentése egyenes vagy elágazó láncú (CrC$)alkH vagy (Cs-Cgjcskloalkil; Rg jelentése egyenes vagy elágazó láncú {Ci-Gg)alk|l vagy (C;rCs)dkloaíkli; R§ jelentése egyenes vagy elágazó láncú (Gi-Gs)alkll vagy (Ca-Cejclkloalkil: vagy R8 és R& a nitrogénatommal együtt, amelyhez kapcsolódnak, plrrolldln-, piperidim vagy morfotíngyörüt alkot; R ;o jelentése egyenes vagy elágazó láncú (Ci~C8}alkíl vagy (Cs-Csjcíkioalkil; R11 jelentése egyenes vagy elágazó láncú (Ci-Cs)aíkíl vagy {Cg-Cgjcikloalkll; R12 jelentése egyenes vagy elágazó láncú (G-rCg jatki vagy (Gj-Cejclkloalkll; R1.3. jelentése egyenes vagy elágazó láncé (C r€§}aM vagy (Ga-Gsjciktoafki; vagy R12 és R13 a nitrogénatommal együtt amelyhez kapcsolódnak, plrrolldln-, piperidln-vagy morfollngyíírűt alkot; Ru jelentése egyenes vagy elágazd láncú (Ci~Cs)aíkíl vagy {Cg-Ggjoikloalkl; Ris jelentése egyenes vagy elágazó láncú (Ci-C-«}alkíl vagy (C 3 ~ C e) cl kl oa I k lí : Ris Jelentése egyenes vagy elágazó láncú (CrCgjaíkíl vagy fCs-Geicíkloaikit; vagy Ri$ és R1§ a htrcgénatommal együtt, amelyhez kapcsolódnak, plrrolldln-, pfperldkv vagy morfolingyürüt alkot; Λ jelentése H egyenes vagy elágazó láncú (CrCgjalklI, (Cs-Cejcikloalkil, OR;i, NH2, NHR's vagy NR3R4; L jelentése egyszeres kötés, -CHr, vagy ~GH2~CH{Rí> Z Jelentése NH vagy O; Ra jelentése egyenes vagy elágazó láncú (Ci-Cg)alkilt egyenes vagy elágazó láncú (C;rC6)alkenll, (Cs-Cejclkloalkil vagy fenil; Rb jelentése egyenes vagy elágazó láncú jGi-Cgjalkil, egyenes vagy elágazó láncú (Cz-Cgjalkenil, (Cs-Cejolklcalkf vagy fenil; Re jelentése egyenes vagy elágazó láncé (G<-C$)aíkti( egyenes vagy elágazó láncú (Ca-Cejalkenif CCs-Csjcikloafkií vagy fenII; Rt jelentése egyenes vagy elágazó láncú (Ci-Cs)alkii vagy (Cs-Cejclkloaikll; R’s jelentése egyenes vagy elágazó láncú (Ci-Cs)ai'kls vagy (Cs-Cejcikloalkll; rums/m R!3 jelentése egyenes vagy elágazó láncé (C-rCg)aÍkis vagy {Cs-Cçjcskioaikll: R!4 jelentése egyenes vagy elágazó láncé (Ci~Cs)aW vagy (Cs-Cgjclkioaíkií, vagy Rk és R4 a nifrogénaiommal együtt, amelyhez kapcsolódnak, pirroiídín-, piperidin-vagy morfoíingyOrüt alkot; Rl jelentése H: egyenes vagy elágazó láncú (Ci-Cejsíkll vagy (C;rC§)dkloalkll; n értéke 0 és 1 közül választott egész szám; p értéke 2, 3 és 4 közül választott egész szám; s értéke 8 és 1 közül választott egész szám; t értéke 0 és 1 közül választott egész szám; reakcióját (I¥) képietű vegyüleítel:(IV) adói a képletben; Rd jelentése egyenes vagy elágazó láncú fCi~C$)alkil; Re, Rí és Rg jelentése egymástól függetlenül egyenes vagy elágazó láncú (Ci-Ce)-alkil, egyenes vagy elágazó láncú (Cc-Cs)aikenll (CrCsjolkioalkl! vagy fenií, Wi és w2 értéke egymástól függetlenül 0 vagy 1, egy alkanol/víz keverékben, ahol az alkanol 1-8 szénatomos egyenes vagy e.agazo láncú alkanol,
- 2. Az 1. igénypont szerinti eljárás, továbbá azzal Jellemezve, begy egy alábbiakból álló csoportból választott nitrogéntartalmú bázikus vegyüieí jelenétében végezzük: ammónia, monoaikil-amin, dialklí-amm, trialkil-amln, monoalkanol-arnin, dl-alkanol-amin, és tnalkanoi-amln, ahol mind az alkil- és mind az alkanolcsoportok 1-6 szénatomos egyenes vagy elágazó láncú csoportok,
- 3. Az 1. vagy 2, Igénypont szerinti eljárás, atiol az alkanolMz keverék egy eianoí/vi'z keverék,
- 4. Az 1-3, Igénypontok bármelyike szerinti elírással előállított progresszív fotoprotektlv organoszilíkon polimer, azzal Jellemezve, hogy mikro- vagy nanorészecske alakjában található. §> A 4. Igénypont szerinti progresszív íotoprotektiv organoszlükon polimer alkalmazása emberi vagy állati élő testet UV sugárzás ellen védő kozmetikai vagy bőrgyógyászati készítmény előállítására, 7 S, A 4. igénypont szerinti fotoprotektiv polimer alkalmazása UY abszorberek fotokémiai prekurzoraként. 7. Â 4. igénypont szerinti fotoprotektiv polimer alkalmazása emberi vagy allai élő testen használatos kozmetikai vagy bőrgyógyászai készítmény előállítására, azzal jellemezve, begy progresszív UV védő hatással rendeikezsk a napon tartózkodás időtartamától és a napsugárzás fokától függően. B. A 4, igénypont szerinti: fotoprotektív polimer emberi vagy állati élő test UV sugárzás elleni megvédésre történő alkalmazásra.
- 9, Kozmetikai vagy bőrgyógyászéi! készítmény, amely egy 4. Igénypont szerinti progresszív fotoprotektiv organoszií ikon polimert vagy annak keverékét foglalja magaban. 10, A 8. igénypont szerinti kozmetikai vagy bőrgyógyászati készítmény, amely egy organoszikon polimer vagy annak keverékének hatékony mennyiségét foglalja magában, amely képes fotokémiáikig ín $itu átalakulni fokozott védőhatású napvédő vegyöletté, 11, A 9, vagy 10. igénypont szerinti kozmetikai vagy bőrgyógyászat! készítmény, azzal jellemezve, hogy a polimerek mennyisége a készítmény összes tömegéhez viszonyítva 0,01 tőmeg:%-fóí 40 tömeg%~ig teljed. 12, A 9-11. igénypontok bármelyike szerinti kozmetikai vagy bőrgyógyászati készítmény, amely továbbá az alábbiak közöl választott napvédő vegyületet tartalmaz; avobenzon, S-etii-hexil-p-meioxi-cinnamannát, oxlbenzon. okiil-dimef il-p-am ino-ben· zoésav, dioxibenzon, etíi-4-[b?sz(hidroxi-propil)]amino-benzoát.. 2~eiíi~hexi!-2~cíán-3„3--difenil-akrílát 2-eil”hexíi-szaliciíát, glíceril-p--amlnobenzoát5 ŐiSjő-tnmeil-oíklohexll--szalídlát, meíLkaníranilát p-dimetii-amino-benzoésav, 2~etH~hexií~p-dímetií~amino~ -benzoát, O-fenii-benzimidazoi-S-szulfonsav., 2-p-dlmefil-amino-feml-5~szulfóniiirn--benzoxazoisav, szulizobenzon, hexíl“2-(4-dietil-amino-2-hidroxi-benzoi!)-benzoát, 2-(4-metii-benzilidén}~kámfor.. és 4-izopropil-dibenzoii-metán.
- 13, Egy (I) képlető monomer;0) '? Ï398S /GM ahol a képleibe a: R jelentéséi az {!}, (|i), (i), és fiv) által alkotott' csoportból választjuk:Rí, % Rss R4 és R$ jelentéséi egymástól függetlenül az alábbiak által alkotót csoport-bői választjuk; H, egyenes vagy elágazó láncú (€rCs)aik?!( fCs-CeJ-cîkloalkll, ORe, NH2í NHR7, NRsRc!; COOH; C0ÖR1Qí CONH2, CONH11.. CONRi2Ri3> S07NH2, SO2NHR14: és Sö2fslRs§Rie; Re jelentése egyenes vagy elágazó láncú (Öt-Cgjafki vagy (Cg-Cgjcíkloalkn; Rt jelentése egyenes vagy elágazó láncú (C-r€s)alkit vagy fCr^cikloalkil; Rs jelentése egyenes vagy elágazó láncú (Ci-Cs)alkli vagy {Cs-Cójcikíoaikli; Rs jelentése egyenes vagy elágazó láncú {Ci-Cgjalkíl vagy (Cs-Cgjeíkloaiki; vagy Rs és Rs a nitrogénatommal együtt, amelyhez kapcsolódnak, pirrolldsn-, plperldln- vagy morfoiingyűrűt alkot; Rio jelentése egyenes vagy elágazó láncú (Ci-Cs)afkií vagy (C.rCg}cikloalkü: R11 jelentése egyenes vagy elágazó láncú (Ci-Cs)aikii vagy (Cs-Cgsdkioaikil; 73398:5/$» Rre jelentése egyenes vagy elágazó láncú (CrCe)alkíl vagy |Cr€g)clkbalkil; Rta jelentése egyenes vagy elágazó Láncú (CrCg)alkii vagy |€r Cs^ókloalki; vagy R;2 és R<3 a nitrogénatommal együtt, amelyhez kapcsolódnak, pirrolidm-, piperídm-vagy morfolingyűröt alkot; R;4 Jelentése egyenes vagy elágazó láncú (Cs-Ceialkll vagy (CsA^dkloalkil; Ri§ Jelentése egyenes vagy elágazó láncú |C*~CsJa!kif vagy (Cs-CsJcikloalkü;. Ri5 jelentése egyenes vagy elágazó láncú (Ci~C$)alkil vagy (C3~Cs)ctkloalkU; vagy Ris és Rt® a nitrogénatommai együtt, amelyhez kapcsolódnak, pirrolídin-, pípendín-vagy modotlngyirűt alkot; A Jelentése H, egyenes vagy elágazó láncú (Ci-CglalkiL (Cs-CeOcikloalkil, ORh, MHa, MHR^vagyNR^; L Jelentése egyszeres kötés, -CHr, vagy ~CH2-CH(Rl}-Z Jelentése MN vagy Ö; Ra jelentése egyenes vagy elágazó láncú JCi-CsJalklL egyenes vagy elágazó láncú (C2-C§}alkenll, ( C 3-Cs) ci kl o a 1 kll vagy lent Rb Jelentése egyenes vagy elágazó láncú (Ci~C§)aikíl. egyenes vagy elágazó láncú (CrCsJaikent (QrCsJctkloalkil vagy lenti; Re Jelentése egyenes vagy elágazó láncú (C-rCgJalkii, egyenes vagy elágazó láncú (Ca-Cgjalkenll, {C3-C§)cikloaikil vagy fenti; R!t Jelentése egyenes vagy elágazó láncú (CrC6)alkli vagy {Cs-Cejdkloalkll; R'2 jelentése egyenes vagy elágazó láncú (Ci-Cs)alkil vagy {C3-C5)cíkloalkíl; R:s Jelentése egyenes vagy elágazó láncú (CrC6)alkíl vagy (C-rC6)dkloalkíl; R4 Jelentése egyenes vagy elágazó láncú (Ci-CeJalkH vagy (Cs-Csjclkloaikll; vagy R’s és R4 a nitrogénatommai együtt, amelyhez kapcsolódnak, pirrolídin-, plperidin-vagy morfolingyűröt alkot; Rt. Jelentése H, egyenes vagy elágazó láncú (C,-Cs.)alkll vagy (Cs-Csjcikioaíkii; n értéke 0 és t közül választott egész szám; p értéke 2, 3 és 4 közöl választott egész szám; s értéke 0 és 1 közül választott egész szám; t értéke 0 és 1 közül választott egész szám; vagy ezek enantiomer formái vagy kozmeikaiiag vagy óörgyógyászatilag elfogadható sói azzal a feltétellel, hogy amikor R Jelentése (i). akkor Ä, L, Z, n; p, s, t, és R1rR§ je- 313§S:3 /δΐ-Σ lenlése nem lehel egyldjüieg H, egyszeres kötés, O. 0, 3. 1, 1, valamint mind nem jelenthet H~t.
- 14, Eljárás a 13. Igénypont szerinti R jelentésében (í) vagy (11) csoportéi viselő monomer előállítására, amely magában foglalja egy (W) képlete vegyőlet reakcióját: ahol a képletben:R' jelentése (!’} vagy (ΙΓ) képletü csoport:és RrRg, A, L és Z jelentése a 13. igénypontban megadott, egy (!!!’} képlelő vegyidéitől :ahol a képletben: Y jelentését az alábbiakból álló csoportból választjuk CL Bt, I, és 0~C~N, és P, s. t, Ra, Rb, és Re jelentése a 13. Igénypontban: megadott, aboi (II’) és (ΙΙΓ) mólaránya az 1:1 arány és 1:2 arány közötti tartományba esik. 1&, Eljárás a 13. Igénypont szerinti R jelentésében (Ili) vagy (Ív) csoportot viselő monomer előállítására, amely magában foglalja egy (If): képlete vegyőlet reakcióját:7I3SS5/GK R" jelentése (ΗΓ) vagy (ív''*) képletet csoportiés R rRs: A és L jelentése a 13. igénypontban megadott, egy (ΙΙΓ) képletü vegyüiettel:X jelentését az alábbiakból álló csoportból választjuk; Cl, Br, és I; p, B, t, Ra, Rb és Re jelentése a 13. igénypontban megadott, és (ír) és ρίΓ5) mófaránya 1:4, A meghatalmazott; ^11^,21¾¾¾¾ 7l39S5/fíK
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DE102015211792A1 (de) | 2015-06-25 | 2016-12-29 | Beiersdorf Ag | Sonnenschutzmittel mit Ausgangsstoff für die Bildung von 4-(tert.-Butyl)-4'-methoxydibenzoylmethan |
DE102015211790A1 (de) | 2015-06-25 | 2016-12-29 | Beiersdorf Ag | Ethanolisches Sonnenschutzmittel mit Ausgangsstoff für die Bildung von 4-(tert.-Butyl)-4'-methoxydibenzoylmethan |
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