CA2777418C - Silyl polymeric benzoic acid ester compounds, uses, and compositions thereof - Google Patents
Silyl polymeric benzoic acid ester compounds, uses, and compositions thereof Download PDFInfo
- Publication number
- CA2777418C CA2777418C CA2777418A CA2777418A CA2777418C CA 2777418 C CA2777418 C CA 2777418C CA 2777418 A CA2777418 A CA 2777418A CA 2777418 A CA2777418 A CA 2777418A CA 2777418 C CA2777418 C CA 2777418C
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- CA
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- Prior art keywords
- linear
- branched
- alkyl
- cycloalkyl
- ppm
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 105
- -1 benzoic acid ester compounds Chemical class 0.000 title claims description 38
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title claims description 14
- 239000005711 Benzoic acid Substances 0.000 title description 6
- 235000010233 benzoic acid Nutrition 0.000 title description 6
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 title description 2
- 229920000642 polymer Polymers 0.000 claims abstract description 46
- 230000003711 photoprotective effect Effects 0.000 claims abstract description 36
- 230000000750 progressive effect Effects 0.000 claims abstract description 33
- 238000002360 preparation method Methods 0.000 claims abstract description 32
- 239000002537 cosmetic Substances 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 29
- 239000000178 monomer Substances 0.000 claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- 230000005855 radiation Effects 0.000 claims abstract description 22
- 230000008569 process Effects 0.000 claims abstract description 19
- 241001465754 Metazoa Species 0.000 claims abstract description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 151
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 119
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 50
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- 230000000475 sunscreen effect Effects 0.000 claims description 34
- 239000000516 sunscreening agent Substances 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 24
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 23
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 15
- 230000006750 UV protection Effects 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 239000002243 precursor Substances 0.000 claims description 9
- 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 8
- 229960005193 avobenzone Drugs 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000006096 absorbing agent Substances 0.000 claims description 7
- 239000002105 nanoparticle Substances 0.000 claims description 7
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 6
- 239000011859 microparticle Substances 0.000 claims description 6
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 6
- 125000000565 sulfonamide group Chemical group 0.000 claims description 6
- 230000036561 sun exposure Effects 0.000 claims description 6
- WSSJONWNBBTCMG-UHFFFAOYSA-N 2-hydroxybenzoic acid (3,3,5-trimethylcyclohexyl) ester Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C1=CC=CC=C1O WSSJONWNBBTCMG-UHFFFAOYSA-N 0.000 claims description 5
- 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 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 4
- 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 4
- 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 claims description 4
- 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 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 claims 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 claims description 4
- 229960000846 camphor Drugs 0.000 claims description 4
- 229960004960 dioxybenzone Drugs 0.000 claims description 4
- UVCJGUGAGLDPAA-UHFFFAOYSA-N ensulizole Chemical compound N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 UVCJGUGAGLDPAA-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 238000011065 in-situ storage Methods 0.000 claims 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 claims description 4
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 claims description 4
- 229960001173 oxybenzone Drugs 0.000 claims description 4
- 230000004224 protection Effects 0.000 claims description 4
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 claims description 4
- 229960000368 sulisobenzone Drugs 0.000 claims description 4
- 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 claims description 3
- 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 3
- 125000005270 trialkylamine group Chemical group 0.000 claims description 2
- 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 claims 1
- 239000002245 particle Substances 0.000 description 55
- 239000012071 phase Substances 0.000 description 47
- WVGJDUYLVYAQNT-UHFFFAOYSA-N [3-(diethylamino)phenyl] benzoate Chemical compound CCN(CC)C1=CC=CC(OC(=O)C=2C=CC=CC=2)=C1 WVGJDUYLVYAQNT-UHFFFAOYSA-N 0.000 description 33
- 239000004480 active ingredient Substances 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 description 17
- 238000004128 high performance liquid chromatography Methods 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 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
- RJQSMMZRWQXFTQ-UHFFFAOYSA-N (3-methoxyphenyl) benzoate Chemical compound COC1=CC=CC(OC(=O)C=2C=CC=CC=2)=C1 RJQSMMZRWQXFTQ-UHFFFAOYSA-N 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 14
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 13
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 13
- LLRZUDIHEZXFGV-UHFFFAOYSA-N (4-methylphenyl) benzoate Chemical compound C1=CC(C)=CC=C1OC(=O)C1=CC=CC=C1 LLRZUDIHEZXFGV-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 12
- 239000004205 dimethyl polysiloxane Substances 0.000 description 12
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 12
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 12
- 125000000753 cycloalkyl group Chemical group 0.000 description 11
- 239000004615 ingredient Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- PMRMHHUTWZPFIY-UHFFFAOYSA-N (4-methoxyphenyl) benzoate Chemical compound C1=CC(OC)=CC=C1OC(=O)C1=CC=CC=C1 PMRMHHUTWZPFIY-UHFFFAOYSA-N 0.000 description 10
- WZFOUELQWJUYIF-UHFFFAOYSA-N [4-(diethylamino)phenyl] benzoate Chemical compound C1=CC(N(CC)CC)=CC=C1OC(=O)C1=CC=CC=C1 WZFOUELQWJUYIF-UHFFFAOYSA-N 0.000 description 10
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- 239000000725 suspension Substances 0.000 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 description 8
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 8
- 229940008099 dimethicone Drugs 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 229920002125 Sokalan® Polymers 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 7
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 7
- 229960002216 methylparaben Drugs 0.000 description 7
- 239000000047 product Substances 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 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 6
- 239000006071 cream Substances 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 6
- 239000006210 lotion Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 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 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 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 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
- 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 5
- 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 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
- 239000004359 castor oil Substances 0.000 description 5
- 235000019438 castor oil Nutrition 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 229910000077 silane Inorganic materials 0.000 description 5
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 4
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 4
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 4
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 4
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-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
- 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
- 238000004587 chromatography analysis Methods 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 229940086555 cyclomethicone Drugs 0.000 description 4
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000003205 fragrance Substances 0.000 description 4
- 229940075529 glyceryl stearate Drugs 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000003094 microcapsule Substances 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
- 239000000126 substance 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
- 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
- RMFFCSRJWUBPBJ-UHFFFAOYSA-N 15-hydroxypentadecyl benzoate Chemical compound OCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1 RMFFCSRJWUBPBJ-UHFFFAOYSA-N 0.000 description 3
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 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 3
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Classifications
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- 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
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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
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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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- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
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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
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- A—HUMAN NECESSITIES
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- A61P17/16—Emollients or protectives, e.g. against radiation
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- A—HUMAN NECESSITIES
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
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- C07F7/02—Silicon compounds
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- C07F7/1804—Compounds having Si-O-C linkages
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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
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
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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
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- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
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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
- C08G77/38—Polysiloxanes modified by chemical after-treatment
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/12—Powdering or granulating
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
Landscapes
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
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- Engineering & Computer Science (AREA)
- Toxicology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Cosmetics (AREA)
- Silicon Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09173122A EP2311844A1 (en) | 2009-10-15 | 2009-10-15 | Silyl polymeric benzoic acid ester compounds, uses, and compositions thereof |
| EP09173122.4 | 2009-10-15 | ||
| PCT/EP2010/065454 WO2011045389A1 (en) | 2009-10-15 | 2010-10-14 | Silyl polymeric benzoic acid ester compounds, uses, and compositions thereof |
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| CA2777418A1 CA2777418A1 (en) | 2011-04-21 |
| CA2777418C true CA2777418C (en) | 2017-05-30 |
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| AP3280A (en) | 2009-03-23 | 2015-05-31 | Glenmark Pharmaceuticals Sa | Fused pyrimidine-dione derivatives as TRPA1 modulators |
| KR101541848B1 (ko) | 2012-11-12 | 2015-08-13 | 현대모비스 주식회사 | 인휠 모터 시스템 |
| AR100211A1 (es) | 2014-05-19 | 2016-09-21 | Interquim Sa | Procedimiento para la preparación de un polímero fotoprotector progresivo de organosilicio; polímero fotoprotector progresivo de organosilicio, su uso, composición que lo comprende, monómero precursor, procedimientos para la preparación de dicho monómero precursor |
| 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 |
| DE102015211793A1 (de) | 2015-06-25 | 2016-12-29 | Beiersdorf Ag | Alkandiol-haltige Sonnenschutzmittel mit Ausgangsstoff für die Bildung von 4-(tert.-Butyl)-4'-methoxydibenzoylmethan |
| DE102015216959A1 (de) | 2015-09-04 | 2017-03-09 | Beiersdorf Ag | Parfümiertes Sonnenschutzmittel mit Ausgangsstoff für die Bildung von 4-(tert.-Butyl)-4'-methoxydibenzoylmethan |
| DE102015225568A1 (de) | 2015-12-17 | 2017-06-22 | Beiersdorf Ag | Neustes Sonnenschutzmittel mit Ausgangsstoff für die Bildung von 4-(tert.-Butyl)-4'-methoxydibenzoylmethan |
| DE102015225570A1 (de) | 2015-12-17 | 2017-06-22 | Beiersdorf Ag | Allerneustes Sonnenschutzmittel mit Ausgangsstoff für die Bildung von 4-(tert.-Butyl)-4'-methoxy-di-ben-zoylmethan |
| DE102015225567A1 (de) | 2015-12-17 | 2017-06-22 | Beiersdorf Ag | Neues Sonnenschutzmittel mit Ausgangsstoff für die Bildung von 4-(tert.-Butyl)-4'-methoxydibenzoylmethan |
| DE102016000800A1 (de) | 2016-01-27 | 2017-07-27 | Beiersdorf Ag | Sonnenschutzmittel mit Tricyclodecanmethylisononanoat |
| KR101881815B1 (ko) * | 2016-02-03 | 2018-08-24 | 한국생산기술연구원 | 알콕시실릴기 및 활성 에스테르기를 갖는 화합물, 이의 제조방법, 이를 포함하는 조성물 및 용도 |
| DE102019203074A1 (de) * | 2019-03-06 | 2020-09-10 | Henkel Ag & Co. Kgaa | Verfahren zur Herstellung von Haarbehandlungsmitteln mit organischen C1-C6-Alkoxy-Silanen |
| DE102019203077A1 (de) * | 2019-03-06 | 2020-09-10 | Henkel Ag & Co. Kgaa | Verfahren zur Herstellung von Haarbehandlungsmitteln mit organischen C1-C6-Alkoxy-Silanen |
| DE102019203675A1 (de) * | 2019-03-19 | 2020-09-24 | Henkel Ag & Co. Kgaa | Verfahren zum Färben von keratinischem Material, umfassend die Anwendung von einer siliciumorganischen Verbindung, eines Effektpigments und eines filmbildenden Polymers V |
| EP4426709A1 (en) * | 2021-11-05 | 2024-09-11 | Fundació Eurecat | Compounds as sun protection agents |
| GB2623090A (en) | 2022-10-04 | 2024-04-10 | Sublino Ltd | Method of colouring |
| JP2025168864A (ja) | 2024-04-30 | 2025-11-12 | 信越化学工業株式会社 | 含窒素多官能オルガノキシシラン化合物の製造方法 |
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| US6274133B1 (en) | 1998-12-22 | 2001-08-14 | Bausch & Lomb Incorporated | Method for treating extended-wear contact lenses in the eyes |
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| US20070190325A1 (en) | 2003-12-04 | 2007-08-16 | Katja Berg-Schultz | Microcapsules with uv filter activity and process for producing them |
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| WO2009101016A2 (de) | 2008-02-12 | 2009-08-20 | Basf Se | Modifizierte hybride nanopartikel |
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