ES2668478T3 - Polímeros de absorción de la radiación ultravioleta - Google Patents
Polímeros de absorción de la radiación ultravioleta Download PDFInfo
- Publication number
- ES2668478T3 ES2668478T3 ES13731628.7T ES13731628T ES2668478T3 ES 2668478 T3 ES2668478 T3 ES 2668478T3 ES 13731628 T ES13731628 T ES 13731628T ES 2668478 T3 ES2668478 T3 ES 2668478T3
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- Prior art keywords
- acid
- chromophore
- mmol
- poly
- glycerol
- Prior art date
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- 230000005855 radiation Effects 0.000 title claims abstract description 20
- 229920000642 polymer Polymers 0.000 title claims description 91
- 238000010521 absorption reaction Methods 0.000 title description 5
- 239000000178 monomer Substances 0.000 claims abstract description 63
- 239000000203 mixture Substances 0.000 claims abstract description 57
- 239000002253 acid Substances 0.000 claims abstract description 27
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 50
- -1 alkane esters Chemical class 0.000 claims description 50
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims description 38
- ARIWANIATODDMH-UHFFFAOYSA-N Lauric acid monoglyceride Natural products CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 claims description 36
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 18
- ARIWANIATODDMH-AWEZNQCLSA-N 1-lauroyl-sn-glycerol Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](O)CO ARIWANIATODDMH-AWEZNQCLSA-N 0.000 claims description 15
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- 150000004820 halides Chemical class 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000001735 carboxylic acids Chemical class 0.000 claims description 6
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 claims description 6
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 claims description 6
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 5
- 239000011976 maleic acid Substances 0.000 claims description 5
- 229920000223 polyglycerol Polymers 0.000 claims description 5
- 229920001296 polysiloxane Polymers 0.000 claims description 5
- 230000000699 topical effect Effects 0.000 claims description 5
- 150000003852 triazoles Chemical class 0.000 claims description 5
- QHZLMUACJMDIAE-UHFFFAOYSA-N 1-monopalmitoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)CO QHZLMUACJMDIAE-UHFFFAOYSA-N 0.000 claims description 4
- 239000007983 Tris buffer Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 4
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 229920001451 polypropylene glycol Polymers 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 3
- MUTZWJYYDYUTBC-UHFFFAOYSA-N 2-benzoyl-6-hydroxybenzoic acid Chemical class OC(=O)C1=C(O)C=CC=C1C(=O)C1=CC=CC=C1 MUTZWJYYDYUTBC-UHFFFAOYSA-N 0.000 claims description 3
- KXTAOXNYQGASTA-UHFFFAOYSA-N 2-benzylidenepropanedioic acid Chemical compound OC(=O)C(C(O)=O)=CC1=CC=CC=C1 KXTAOXNYQGASTA-UHFFFAOYSA-N 0.000 claims description 3
- JKEWHJRARLJYAN-UHFFFAOYSA-N 4-hydroxy-2-oxochromene-3-carboxylic acid Chemical class C1=CC=C2OC(=O)C(C(=O)O)=C(O)C2=C1 JKEWHJRARLJYAN-UHFFFAOYSA-N 0.000 claims description 3
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 claims description 3
- 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 3
- 150000002430 hydrocarbons Chemical group 0.000 claims description 3
- LKUNXBRZDFMZOK-UHFFFAOYSA-N rac-1-monodecanoylglycerol Chemical compound CCCCCCCCCC(=O)OCC(O)CO LKUNXBRZDFMZOK-UHFFFAOYSA-N 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 2
- WECGLUPZRHILCT-GSNKCQISSA-N 1-linoleoyl-sn-glycerol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@@H](O)CO WECGLUPZRHILCT-GSNKCQISSA-N 0.000 claims description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 2
- 235000015165 citric acid Nutrition 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical class C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 2
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 claims description 2
- 150000002016 disaccharides Chemical class 0.000 claims description 2
- 150000004676 glycans Chemical class 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- 235000011090 malic acid Nutrition 0.000 claims description 2
- 150000002772 monosaccharides Chemical class 0.000 claims description 2
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 claims description 2
- 229920001282 polysaccharide Polymers 0.000 claims description 2
- 239000005017 polysaccharide Substances 0.000 claims description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims 3
- 241000723346 Cinnamomum camphora Species 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 229930008380 camphor Natural products 0.000 claims 2
- 229930005346 hydroxycinnamic acid Natural products 0.000 claims 2
- 235000010359 hydroxycinnamic acids Nutrition 0.000 claims 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 2
- NGSWKAQJJWESNS-ZZXKWVIFSA-N trans-4-coumaric acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C=C1 NGSWKAQJJWESNS-ZZXKWVIFSA-N 0.000 claims 2
- 229940035437 1,3-propanediol Drugs 0.000 claims 1
- LKUNXBRZDFMZOK-GFCCVEGCSA-N Capric acid monoglyceride Natural products CCCCCCCCCC(=O)OC[C@H](O)CO LKUNXBRZDFMZOK-GFCCVEGCSA-N 0.000 claims 1
- 150000001279 adipic acids Chemical class 0.000 claims 1
- 229960004050 aminobenzoic acid Drugs 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- 150000002311 glutaric acids Chemical class 0.000 claims 1
- 150000002334 glycols Chemical class 0.000 claims 1
- 150000001261 hydroxy acids Chemical class 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
- 150000003047 pimelic acids Chemical class 0.000 claims 1
- 229960004889 salicylic acid Drugs 0.000 claims 1
- 150000003330 sebacic acids Chemical class 0.000 claims 1
- 150000003442 suberic acids Chemical class 0.000 claims 1
- 150000003444 succinic acids Chemical class 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 64
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 40
- 239000000243 solution Substances 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 35
- DLAHAXOYRFRPFQ-UHFFFAOYSA-N dodecyl benzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=CC=C1 DLAHAXOYRFRPFQ-UHFFFAOYSA-N 0.000 description 33
- 238000006116 polymerization reaction Methods 0.000 description 33
- 239000007787 solid Substances 0.000 description 33
- 239000003921 oil Substances 0.000 description 31
- 235000019198 oils Nutrition 0.000 description 31
- 238000003756 stirring Methods 0.000 description 31
- 238000005160 1H NMR spectroscopy Methods 0.000 description 29
- 238000005227 gel permeation chromatography Methods 0.000 description 23
- 239000010410 layer Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 238000004128 high performance liquid chromatography Methods 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000000725 suspension Substances 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- 235000019439 ethyl acetate Nutrition 0.000 description 17
- 238000002390 rotary evaporation Methods 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- BOZRCGLDOHDZBP-UHFFFAOYSA-N 2-ethylhexanoic acid;tin Chemical compound [Sn].CCCCC(CC)C(O)=O BOZRCGLDOHDZBP-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 14
- 229910001868 water Inorganic materials 0.000 description 14
- 229940075507 glyceryl monostearate Drugs 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- 239000002244 precipitate Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 125000000524 functional group Chemical group 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
- 238000000338 in vitro Methods 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 239000007832 Na2SO4 Substances 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 238000002835 absorbance Methods 0.000 description 7
- 239000012267 brine Substances 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 229920001971 elastomer Polymers 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 229920005862 polyol Polymers 0.000 description 7
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002250 absorbent Substances 0.000 description 6
- 230000002745 absorbent Effects 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 6
- 239000004205 dimethyl polysiloxane Substances 0.000 description 6
- 229940068939 glyceryl monolaurate Drugs 0.000 description 6
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 230000000475 sunscreen effect Effects 0.000 description 5
- 239000000516 sunscreening agent Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 4
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 4
- 239000012964 benzotriazole Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
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- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- 239000000263 2,3-dihydroxypropyl (Z)-octadec-9-enoate Substances 0.000 description 3
- RZRNAYUHWVFMIP-GDCKJWNLSA-N 3-oleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-GDCKJWNLSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 101150065749 Churc1 gene Proteins 0.000 description 3
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- 208000000453 Skin Neoplasms Diseases 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
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- 238000004821 distillation Methods 0.000 description 3
- LJDNMOCAQVXVKY-UHFFFAOYSA-N ethyl 2-[(2-ethoxy-2-oxoethyl)amino]acetate Chemical compound CCOC(=O)CNCC(=O)OCC LJDNMOCAQVXVKY-UHFFFAOYSA-N 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
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- 201000000849 skin cancer Diseases 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 239000001384 succinic acid Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 238000003828 vacuum filtration Methods 0.000 description 3
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- IQUCNXSZNHPPML-UHFFFAOYSA-N 2-chloro-n-[(4-chlorophenyl)-phenylmethyl]acetamide Chemical compound C=1C=C(Cl)C=CC=1C(NC(=O)CCl)C1=CC=CC=C1 IQUCNXSZNHPPML-UHFFFAOYSA-N 0.000 description 2
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 2
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- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 125000005500 uronium group Chemical group 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000037303 wrinkles Effects 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
- A61K8/72—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
- A61K8/85—Polyesters
-
- 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
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/52—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
- C08G63/54—Polycarboxylic acids or polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation the acids or hydroxy compounds containing carbocyclic rings
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/685—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen
- C08G63/6854—Polyesters containing atoms other than carbon, hydrogen and oxygen containing nitrogen derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6856—Dicarboxylic acids and dihydroxy compounds
-
- 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
- A61K2800/57—Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Cosmetics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261665430P | 2012-06-28 | 2012-06-28 | |
| US201261665430P | 2012-06-28 | ||
| US13/799,193 US9469725B2 (en) | 2012-06-28 | 2013-03-13 | Ultraviolet radiation absorbing polymers |
| US201313799193 | 2013-03-13 | ||
| PCT/US2013/046348 WO2014004176A1 (en) | 2012-06-28 | 2013-06-18 | Ultraviolet radiation absorbing polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2668478T3 true ES2668478T3 (es) | 2018-05-18 |
Family
ID=49778385
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES13731628.7T Active ES2668478T3 (es) | 2012-06-28 | 2013-06-18 | Polímeros de absorción de la radiación ultravioleta |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US9469725B2 (OSRAM) |
| EP (1) | EP2866898B1 (OSRAM) |
| KR (1) | KR102057876B1 (OSRAM) |
| CN (1) | CN104411366B (OSRAM) |
| AU (1) | AU2013280915B2 (OSRAM) |
| BR (1) | BR112014032814A8 (OSRAM) |
| CA (1) | CA2877476C (OSRAM) |
| ES (1) | ES2668478T3 (OSRAM) |
| IN (1) | IN2014DN11009A (OSRAM) |
| RU (1) | RU2642974C2 (OSRAM) |
| TW (1) | TWI598375B (OSRAM) |
| WO (1) | WO2014004176A1 (OSRAM) |
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| US9255180B2 (en) | 2012-06-28 | 2016-02-09 | Johnson & Johnson Consumer Inc. | Ultraviolet radiation absorbing polyethers |
| WO2014004477A2 (en) | 2012-06-28 | 2014-01-03 | Johnson & Johnson Consumer Companies, Inc. | Sunscreen compositions containing an ultraviolet radiation-absorbing polymer |
| CN107729083B (zh) * | 2014-04-30 | 2021-02-12 | 华为技术有限公司 | 一种加载驱动程序的方法及嵌入式设备 |
| US10246552B1 (en) * | 2016-07-13 | 2019-04-02 | SurfTech Corporation | Photostabilizing polymer |
| ES2939594T3 (es) * | 2016-10-05 | 2023-04-25 | Basf Se | Composición polimérica absorbente de radiación ultravioleta |
| EP3592781B1 (en) * | 2017-03-09 | 2021-02-17 | Ecolab USA Inc. | Polymerization inhibitor compositions |
| CN108703892B (zh) * | 2018-07-27 | 2021-05-11 | 广州汇朗生物科技有限公司 | 1,5-戊二醇的新应用 |
| ES3012259T3 (en) | 2019-10-02 | 2025-04-09 | Basf Se | Compositions with polymeric or oligomeric hydroxy phenyl triazine uv filter |
| KR20230124643A (ko) * | 2020-12-23 | 2023-08-25 | 모멘티브 퍼포먼스 머티리얼즈 인크. | 바이오재생가능 엘라스토머 겔 및 이의 용도 |
| CN115403734A (zh) * | 2022-10-08 | 2022-11-29 | 安徽泓泽新材料科技有限公司 | 一种呔哔克基聚酯固化剂及其制备方法 |
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| US20100129303A1 (en) | 2008-10-17 | 2010-05-27 | Dueva-Koganov Olga V | Sunscreen and personal care compositions comprising a random terpolymer |
| US9044623B2 (en) | 2009-01-27 | 2015-06-02 | Isp Investments Inc. | Polymer-bound UV absorbers in personal care compositions |
| BRPI1006352A2 (pt) | 2009-03-13 | 2015-08-25 | Basf Se | " composição agroquímica, absorvedor de uv da fórmula iii, uso dos absorventes de uv e método de controle de fungo fitopatogênico " |
| CN102712744A (zh) | 2009-11-02 | 2012-10-03 | 伊诺莱克斯投资公司 | Uv吸收性复合聚酯聚合物，包含uv吸收性复合聚酯聚合物的组合物，和相关方法 |
| KR20120115510A (ko) | 2009-12-09 | 2012-10-18 | 디에스엠 아이피 어셋츠 비.브이. | 신규 화합물 |
| DE102009059104A1 (de) | 2009-12-18 | 2011-06-22 | Johannes-Gutenberg-Universität Mainz, 55122 | Funktionelle verzweigte Polyether Copolymere sowie Verfahren zu ihrer Herstellung |
| US8475774B2 (en) | 2010-02-08 | 2013-07-02 | Johnson & Johnson Consumer Companies, Inc. | Sunscreen compositions comprising an ultraviolet radiation-absorbing polymer |
| US8211850B2 (en) | 2010-11-15 | 2012-07-03 | Johnson & Johnson Consumer Companies, Inc. | Polyglyceryl compounds and compositions |
| WO2014004477A2 (en) | 2012-06-28 | 2014-01-03 | Johnson & Johnson Consumer Companies, Inc. | Sunscreen compositions containing an ultraviolet radiation-absorbing polymer |
-
2013
- 2013-03-13 US US13/799,193 patent/US9469725B2/en active Active
- 2013-06-18 RU RU2015102541A patent/RU2642974C2/ru active
- 2013-06-18 KR KR1020157001825A patent/KR102057876B1/ko active Active
- 2013-06-18 ES ES13731628.7T patent/ES2668478T3/es active Active
- 2013-06-18 IN IN11009DEN2014 patent/IN2014DN11009A/en unknown
- 2013-06-18 CN CN201380034690.6A patent/CN104411366B/zh active Active
- 2013-06-18 WO PCT/US2013/046348 patent/WO2014004176A1/en not_active Ceased
- 2013-06-18 BR BR112014032814A patent/BR112014032814A8/pt not_active Application Discontinuation
- 2013-06-18 EP EP13731628.7A patent/EP2866898B1/en active Active
- 2013-06-18 AU AU2013280915A patent/AU2013280915B2/en active Active
- 2013-06-18 CA CA2877476A patent/CA2877476C/en active Active
- 2013-06-27 TW TW102122895A patent/TWI598375B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| RU2642974C2 (ru) | 2018-01-29 |
| TW201410732A (zh) | 2014-03-16 |
| EP2866898A1 (en) | 2015-05-06 |
| WO2014004176A1 (en) | 2014-01-03 |
| US9469725B2 (en) | 2016-10-18 |
| BR112014032814A8 (pt) | 2022-08-16 |
| KR20150027241A (ko) | 2015-03-11 |
| RU2015102541A (ru) | 2016-08-20 |
| CN104411366B (zh) | 2017-09-08 |
| CA2877476C (en) | 2021-01-26 |
| CA2877476A1 (en) | 2014-01-03 |
| CN104411366A (zh) | 2015-03-11 |
| KR102057876B1 (ko) | 2020-02-07 |
| BR112014032814A2 (pt) | 2017-06-27 |
| IN2014DN11009A (OSRAM) | 2015-09-25 |
| TWI598375B (zh) | 2017-09-11 |
| AU2013280915A1 (en) | 2015-01-22 |
| EP2866898B1 (en) | 2018-04-04 |
| US20140004060A1 (en) | 2014-01-02 |
| AU2013280915B2 (en) | 2017-09-07 |
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