EP0101699A1 - Verwendung von 2-(1-oxo-alkyl)-5-phenyl-2,4-pentadiensäure-estern als lichtschutzfiltersubstanzen - Google Patents
Verwendung von 2-(1-oxo-alkyl)-5-phenyl-2,4-pentadiensäure-estern als lichtschutzfiltersubstanzenInfo
- Publication number
- EP0101699A1 EP0101699A1 EP83900710A EP83900710A EP0101699A1 EP 0101699 A1 EP0101699 A1 EP 0101699A1 EP 83900710 A EP83900710 A EP 83900710A EP 83900710 A EP83900710 A EP 83900710A EP 0101699 A1 EP0101699 A1 EP 0101699A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- phenyl
- alkyl
- oxo
- radical
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000000126 substance Substances 0.000 title claims abstract description 23
- 239000002253 acid Substances 0.000 title claims abstract 7
- 150000002148 esters Chemical class 0.000 title claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 239000002537 cosmetic Substances 0.000 claims abstract description 12
- -1 cyclic alkyl radical Chemical class 0.000 claims description 31
- 238000002360 preparation method Methods 0.000 claims description 13
- 239000003921 oil Substances 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000004611 light stabiliser Substances 0.000 claims description 6
- 239000006096 absorbing agent Substances 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000006071 cream Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 235000013336 milk Nutrition 0.000 claims description 3
- 239000008267 milk Substances 0.000 claims description 3
- 210000004080 milk Anatomy 0.000 claims description 3
- 239000007921 spray Substances 0.000 claims description 3
- COBPKKZHLDDMTB-UHFFFAOYSA-N 2-[2-(2-butoxyethoxy)ethoxy]ethanol Chemical group CCCCOCCOCCOCCO COBPKKZHLDDMTB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims description 2
- 239000005022 packaging material Substances 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 229920003023 plastic Polymers 0.000 claims description 2
- 239000011241 protective layer Substances 0.000 claims description 2
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 claims 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims 1
- 239000012050 conventional carrier Substances 0.000 claims 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 claims 1
- MDLWEBWGXACWGE-UHFFFAOYSA-N octadecane Chemical compound [CH2]CCCCCCCCCCCCCCCCC MDLWEBWGXACWGE-UHFFFAOYSA-N 0.000 claims 1
- 239000011814 protection agent Substances 0.000 claims 1
- 239000012209 synthetic fiber Substances 0.000 claims 1
- 229920002994 synthetic fiber Polymers 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 19
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 230000005855 radiation Effects 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 150000002576 ketones Chemical class 0.000 description 9
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- 150000001336 alkenes Chemical class 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- YYJKMSKFMXYIKW-UHFFFAOYSA-N 2-acetyl-5-phenylpenta-2,4-dienoic acid Chemical compound CC(=O)C(C(O)=O)=CC=CC1=CC=CC=C1 YYJKMSKFMXYIKW-UHFFFAOYSA-N 0.000 description 5
- 229940117916 cinnamic aldehyde Drugs 0.000 description 5
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 5
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 5
- 125000000913 palmityl 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])C([H])([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 description 5
- 239000002304 perfume Substances 0.000 description 5
- 239000005662 Paraffin oil Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 230000037072 sun protection Effects 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 206010042496 Sunburn Diseases 0.000 description 3
- 229960000541 cetyl alcohol Drugs 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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 description 3
- 210000002268 wool Anatomy 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 206010015150 Erythema Diseases 0.000 description 2
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 231100000321 erythema Toxicity 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 235000010944 ethyl methyl cellulose Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- PIUVNPNBPWVVKZ-UHFFFAOYSA-N octadecyl 2-ethylhexanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(CC)CCCC PIUVNPNBPWVVKZ-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000000475 sunscreen effect Effects 0.000 description 2
- 239000000516 sunscreening agent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- SJCUPJATWUWGAV-UHFFFAOYSA-N 2-(3-oxobutanoyloxy)ethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC(=O)CC(C)=O SJCUPJATWUWGAV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QAUIAXORENGBSN-UHFFFAOYSA-N 2-ethylhexyl 3-oxobutanoate Chemical compound CCCCC(CC)COC(=O)CC(C)=O QAUIAXORENGBSN-UHFFFAOYSA-N 0.000 description 1
- NPSJHQMIVNJLNN-UHFFFAOYSA-N 2-ethylhexyl 4-nitrobenzoate Chemical compound CCCCC(CC)COC(=O)C1=CC=C([N+]([O-])=O)C=C1 NPSJHQMIVNJLNN-UHFFFAOYSA-N 0.000 description 1
- WOYWLLHHWAMFCB-UHFFFAOYSA-N 2-ethylhexyl acetate Chemical compound CCCCC(CC)COC(C)=O WOYWLLHHWAMFCB-UHFFFAOYSA-N 0.000 description 1
- 239000004808 2-ethylhexylester Substances 0.000 description 1
- PRRBQHNMYJRHFW-UHFFFAOYSA-M 3-oxoheptanoate Chemical compound CCCCC(=O)CC([O-])=O PRRBQHNMYJRHFW-UHFFFAOYSA-M 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- HBTAOSGHCXUEKI-UHFFFAOYSA-N 4-chloro-n,n-dimethyl-3-nitrobenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 HBTAOSGHCXUEKI-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- BKIRHERWCGYKBG-UHFFFAOYSA-N CCCC(C(CC)=O)=CC=CC1=CC=CC=C1 Chemical compound CCCC(C(CC)=O)=CC=CC1=CC=CC=C1 BKIRHERWCGYKBG-UHFFFAOYSA-N 0.000 description 1
- OELQCXKRIPDIOP-UHFFFAOYSA-N CCCCCCCCCCCCCCCCCCOC(=O)C(C(C)=O)=CC=CC1=CC=CC=C1 Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C(C)=O)=CC=CC1=CC=CC=C1 OELQCXKRIPDIOP-UHFFFAOYSA-N 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000283153 Cetacea Species 0.000 description 1
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 102000053602 DNA Human genes 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- 102000016942 Elastin Human genes 0.000 description 1
- 108010014258 Elastin Proteins 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- 102000011782 Keratins Human genes 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 208000000453 Skin Neoplasms Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical class CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical group OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical class C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- DOYKFDRIECFSJW-UHFFFAOYSA-N diethyl 2-propanoylpropanedioate Chemical compound CCOC(=O)C(C(=O)CC)C(=O)OCC DOYKFDRIECFSJW-UHFFFAOYSA-N 0.000 description 1
- 229940031578 diisopropyl adipate Drugs 0.000 description 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 229920002549 elastin Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- IEEXOFJUVNOCME-UHFFFAOYSA-N ethyl 2-acetyl-5-phenylpenta-2,4-dienoate Chemical compound CCOC(=O)C(C(C)=O)=CC=CC1=CC=CC=C1 IEEXOFJUVNOCME-UHFFFAOYSA-N 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- UPHJCAWJZCDVIM-UHFFFAOYSA-N ethyl 2-methyl-5-phenylpenta-2,4-dienoate Chemical compound CCOC(=O)C(C)=CC=CC1=CC=CC=C1 UPHJCAWJZCDVIM-UHFFFAOYSA-N 0.000 description 1
- AYDOTEURWQTZSQ-UHFFFAOYSA-N ethyl 3-oxo-7-phenylhepta-4,6-dienoate Chemical compound C(C)OC(CC(=O)C=CC=CC1=CC=CC=C1)=O AYDOTEURWQTZSQ-UHFFFAOYSA-N 0.000 description 1
- 239000001761 ethyl methyl cellulose Substances 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 229920003087 methylethyl cellulose Polymers 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000001117 oleyl 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])/C([H])=C([H])\C([H])([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 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229940113115 polyethylene glycol 200 Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920002477 rna polymer Polymers 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 201000000849 skin cancer Diseases 0.000 description 1
- 230000037394 skin elasticity Effects 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
Definitions
- Sunlight consists of radiation components of different wavelength ranges. In addition to visible light, there is also infrared (IR) and ultraviolet (UV) radiation.
- IR infrared
- UV ultraviolet
- the high-energy UV radiation contained in sunlight causes tanning of the skin, but also "sunburn” (erythema) [overview - in: W. Bruhn, Deutsche maschiner-Zeitung, 117, 1159-1162, 1362-1366, 1872-1876 (1977)].
- the UV part of the sunlight is divided into three areas:
- UV-A UV-A
- Methyl shows the relatively small decrease in absorbance with long-term radiation (1, 3 and 6 hours).
- the other esters of general formula 1 also show a UV maximum at 330 nm due to the same chromophoric group, however due to the different molecular weights, each with a different specific absorbance.
- the radiation stability corresponds to that of the ethyl ester.
- the substances of general formula 1 are liquid and can be easily incorporated into a wide variety of cosmetic formulations and are stable to emulsions. Self-odor and self-discoloration are low.
- the compound of the general formula 1 does not change or discolor significantly under the influence of prolonged exposure to sunlight, it protects the material to which it was incorporated, but also the layers underneath, for a long time.
- the compounds of formula 1 can be used alone or in combination with other UV absorbers in sunscreen cosmetics of various preparation forms (oil, cream, milk, spray), using customary carrier materials, diluents, fillers and auxiliaries. Examples of such materials are:
- Natural and synthetic glycerides Natural and synthetic glycerides, natural and synthetic waxes, paraffin, whale, fatty acids, fatty alcohols (stearyl, oleyl, palmityl, cetyl alcohol etc.), Eucerin (5% wool fatty alcohols and 95% aliphatic hydrocarbons), wool fat, sorbitan fatty acid esters , Polyethylene sorbitan fatty acid esters, fatty alcohol polyglycol ethers and esters, carboxyvinyl polymers, gelatin, tragacanth, pectins, agar agar, methyl, ethyl or carboxymethyl cellulose or polyacrylic acid (as carrier)
- - lower alcohols such as ethanol, isopropanol and glycols, Polyalcohols (ethylene glycol, glycerin) or water (as a solvent), - ionogenic or non-ionic, cation- or anion-active, or ampholytic emulsifiers, preservatives, dyes and perfume compositions (as auxiliaries).
- the compounds of formula 1 are also suitable as light stabilizers for natural fibers such as cotton or wool (delaying or preventing the fading of colors), or for films, foils, threads, fibers and other molded articles made of synthetic plastics and as a component of filters and protective layers for photographic purposes or packaging material.
- the content of compounds of formula 1 in cosmetic or technical applications is not critical per se and largely depends on the intended use. In general, the concentration in the end product can be 0.1 to 10% (but also more).
- the compounds of formula 1 are easy to prepare.
- esters of general formula 1 can be prepared from cinnamaldehyde (5) and a 1-oxo-alkyl-carboxylic acid ester (6), strong organic bases such as piperidine or pyrrolidine being used with preference, even in the presence of weak organic acids were.
- strong organic bases such as piperidine or pyrrolidine being used with preference, even in the presence of weak organic acids were.
- the compounds 1 are each present as a mixture of isomers (approx. 2: 3).
- the UV-A light protection filter substances 2 and 3 already on the market have absorption maxima at ⁇ - 340 or 355 nm and must therefore be used in combination with a UV-B filter substance.
- the compounds of formula 1 can be incorporated in concentrations of 0.1 to 10 5%, preferably 0.5 to 5%, in different cosmetic preparations such as oils, creams, lotions or in preparations for technical applications.
- the compounds of formula 1 which because of the same chromophoric group each have the same absorption behavior in the UV range, have different physical properties (for example viscosity).
- the compounds 1 can therefore advantageously be used in various cosmetic or technical preparation forms.
- a sun protection oil was obtained which can be applied directly or in the form of a spray to the skin.
- Triglyceride of caprylic and capric acid (1: 1) 10.0 g cetyl and stearyl alcohol (1: 1) 2.0 g cetyl / stearyl- ⁇ -ethylhexanoate (approx. 1: 1) 4.0 g isopropyl palmitate 6, 0 g stearyl / cetyl polyglycol ether 7.0 g silicone oil CP 100 0.5 g 2-acetyl-5-phenyl-2,4-pentadienoic acid ester of the formula 1 [preferential with triethylene glycol butyl ether residue, or ethylene glycol or 1.4 butanediol residue (as diester)] 4.0 g of perfume oil 0.5 g 34 0 g
- Example 8 The constituents are emulsified at 70 ° C. as in Example 4, Example 8
- Alkyl polyglycol emulsifier 2.0 g
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3206586 | 1982-02-24 | ||
| DE3206586A DE3206586C1 (de) | 1982-02-24 | 1982-02-24 | Verwendung von 2-Acetyl-5-phenyl-2,4-pentadiensaeureestern als Lichtschutzfiltersubstanzen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0101699A1 true EP0101699A1 (de) | 1984-03-07 |
Family
ID=6156564
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP83900710A Withdrawn EP0101699A1 (de) | 1982-02-24 | 1983-02-24 | Verwendung von 2-(1-oxo-alkyl)-5-phenyl-2,4-pentadiensäure-estern als lichtschutzfiltersubstanzen |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0101699A1 (ja) |
| JP (1) | JPS59500374A (ja) |
| DE (1) | DE3206586C1 (ja) |
| IT (1) | IT1160197B (ja) |
| WO (1) | WO1983002941A1 (ja) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3938468A1 (de) * | 1989-11-18 | 1991-05-23 | Basf Ag | 1,1-dialkoxy-2-oxo-6-aryl-3,5-alkadiene |
| AR020923A1 (es) | 1998-10-23 | 2002-06-05 | Unilever Nv | Una composicion de filtro solar |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2381886A (en) * | 1945-08-14 | Esters | ||
| US3125597A (en) * | 1964-03-17 | chj oh | ||
| US3002992A (en) * | 1958-10-10 | 1961-10-03 | Givaudan Corp | Alkoxyalkyl esters of p-methoxycinnamic acid |
-
1982
- 1982-02-24 DE DE3206586A patent/DE3206586C1/de not_active Expired
-
1983
- 1983-02-24 EP EP83900710A patent/EP0101699A1/de not_active Withdrawn
- 1983-02-24 WO PCT/EP1983/000050 patent/WO1983002941A1/en not_active Application Discontinuation
- 1983-02-24 JP JP58500805A patent/JPS59500374A/ja active Pending
- 1983-02-24 IT IT19757/83A patent/IT1160197B/it active
Non-Patent Citations (1)
| Title |
|---|
| See references of WO8302941A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| IT8319757A0 (it) | 1983-02-24 |
| DE3206586C1 (de) | 1983-07-21 |
| JPS59500374A (ja) | 1984-03-08 |
| WO1983002941A1 (en) | 1983-09-01 |
| IT1160197B (it) | 1987-03-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69815449T2 (de) | Filtrierendes Kosmetisches Mittel | |
| EP0005182B1 (de) | Lichtschutzmittel | |
| DE2544180C2 (de) | Lichtschutzmittel für kosmetische Zwecke | |
| DE2533467C3 (ja) | ||
| EP0114607A1 (de) | Neue Dibenzoyl-methan-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE68904529T2 (de) | Derivate der 5-benzyliden-3-oxacyclopentanone, ihr herstellungsverfahren und ihre verwendung in kosmetischen zusammensetzungen zum schutz der haut und der haare gegen sonnenstrahlung. | |
| DE3742690A1 (de) | Kosmetisches mittel, welches hydroxylderivate von chalkon enthaelt, und dessen verwendung zum schutze der haut und der haare vor lichtstrahlen, neue hydroxylierte chalkonderivate, sowie verfahren zu deren herstellung | |
| DE2102172C3 (de) | Neue Mittel zur Behandlung und Pflege der Haut | |
| EP0486885B1 (de) | Verwendung von Arylpolyencarbonsäuren und ihren Derivaten als Lichtschutzmittel in kosmetischen Zubereitungen | |
| DE3445365C2 (de) | 3-Benzylidenkampferderivate, Verfahren zu deren Herstellung und diese enthaltende kosmetische Mittel | |
| DE69500575T2 (de) | Neue Sonnenschutzfilter, diese enthaltende kosmetische Sonnenschutzmittel und deren Verwendungen | |
| DE2347928A1 (de) | Schutzmittel gegen aktinische strahlen und dieses enthaltende mittel | |
| DE1492274C (ja) | ||
| EP0101699A1 (de) | Verwendung von 2-(1-oxo-alkyl)-5-phenyl-2,4-pentadiensäure-estern als lichtschutzfiltersubstanzen | |
| EP0044970B1 (de) | Verwendung von verätherten 2-(4-Hydroxybenzyliden)-gamma-butyrolactonen als Lichtschutzmittel | |
| EP0207287A2 (de) | Indolinderivate, Verfahren zu ihrer Herstellung und diese Indolinderivate enthaltende kosmetische Lichtschutzmittel | |
| EP0044976A2 (de) | Verwendung von verätherten p-Hydroxyzimtsäureestern als Lichtschutzmittel | |
| CH643807A5 (de) | Ultraviolette strahlen absorbierendes mittel. | |
| DE3028503A1 (de) | Polyalkoxycarbinolzimtsaeureester, verfahren zu ihrer herstellung und diese enthaltende lichtschutzmittel | |
| CH648753A5 (de) | Lichtschutzmittel. | |
| EP0857058B1 (de) | Substituierte benzylidencyanessigester | |
| WO1991002515A1 (de) | Entzündungshemmende wirkstoffe für kosmetische präparate | |
| DE3231705A1 (de) | Verwendung von verzweigtkettigen 2-ethylhexansaeure-estern als bestandteil kosmetischer mittel | |
| DE68910502T2 (de) | Ultraviolett absorbierendes kosmetikum. | |
| DE3843325C2 (de) | Ungesättigte 3-Benzyliden-Campher-derivate, Verfahren zu deren Herstellung, kosmetische Mittel die diese Verbindungen enthalten und Verfahren zum Schutz der Haut und zum Schutze eines kosmetischen Mittels |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| AK | Designated contracting states |
Designated state(s): AT CH DE FR GB LI NL |
|
| 17P | Request for examination filed |
Effective date: 19840223 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
| 18D | Application deemed to be withdrawn |
Effective date: 19860711 |
|
| RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: BRUNKE, ERNST-JOACHIM |