LU87271A1 - Nouveaux derives insatures liposolubles des benzalmalonates et leur utilisation en tant qu'absorbeurs du rayonnement ultra-violet en cosmetique - Google Patents

Nouveaux derives insatures liposolubles des benzalmalonates et leur utilisation en tant qu'absorbeurs du rayonnement ultra-violet en cosmetique Download PDF

Info

Publication number: LU87271A1
Authority: LU; Luxembourg
Prior art keywords: benzalmalonate; diethyl; allyl; formula; cosmetic composition
Prior art date: 1988-07-08

Application number

LU87271A

Other languages

English (en)

French (fr)

Inventor

Forestier Serge

Lang Gerard

Richard Herve

Original Assignee

Oreal

Priority date (The priority date 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 date listed.)

1988-07-08

Filing date

1988-07-08

Publication date

1990-02-07

1988-07-08 Application filed by Oreal filed Critical Oreal

1988-07-08 Priority to LU87271A priority Critical patent/LU87271A1/fr

1989-07-04 Priority to DE8989401906T priority patent/DE68901162D1/de

1989-07-04 Priority to AT89401906T priority patent/ATE74588T1/de

1989-07-04 Priority to EP89401906A priority patent/EP0350386B1/de

1989-07-05 Priority to US07/375,820 priority patent/US5175340A/en

1989-07-07 Priority to BR898903372A priority patent/BR8903372A/pt

1989-07-07 Priority to AU37935/89A priority patent/AU622195B2/en

1989-07-07 Priority to JP1174336A priority patent/JP2781415B2/ja

1990-02-07 Publication of LU87271A1 publication Critical patent/LU87271A1/fr

Links

239000002537 cosmetic Substances 0.000 title claims abstract description 35
230000005855 radiation Effects 0.000 title claims description 10
239000006096 absorbing agent Substances 0.000 title description 4
239000000203 mixture Substances 0.000 claims abstract description 66
-1 trimethylsiloxy Chemical group 0.000 claims abstract description 31
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
KXTAOXNYQGASTA-UHFFFAOYSA-N 2-benzylidenepropanedioic acid Chemical class OC(=O)C(C(O)=O)=CC1=CC=CC=C1 KXTAOXNYQGASTA-UHFFFAOYSA-N 0.000 claims abstract description 12
150000001875 compounds Chemical class 0.000 claims description 35
239000003921 oil Substances 0.000 claims description 21
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
238000000034 method Methods 0.000 claims description 14
239000006210 lotion Substances 0.000 claims description 12
210000003491 skin Anatomy 0.000 claims description 12
239000000499 gel Substances 0.000 claims description 10
210000002615 epidermis Anatomy 0.000 claims description 9
239000001993 wax Substances 0.000 claims description 9
239000004166 Lanolin Substances 0.000 claims description 7
238000004040 coloring Methods 0.000 claims description 7
229940039717 lanolin Drugs 0.000 claims description 7
235000019388 lanolin Nutrition 0.000 claims description 7
239000000839 emulsion Substances 0.000 claims description 5
239000002304 perfume Substances 0.000 claims description 5
229920005862 polyol Polymers 0.000 claims description 5
150000003077 polyols Chemical class 0.000 claims description 5
239000007787 solid Substances 0.000 claims description 5
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims description 4
238000004061 bleaching Methods 0.000 claims description 4
239000000975 dye Substances 0.000 claims description 4
238000001914 filtration Methods 0.000 claims description 4
239000002562 thickening agent Substances 0.000 claims description 4
239000002671 adjuvant Substances 0.000 claims description 3
239000000443 aerosol Substances 0.000 claims description 3
230000001476 alcoholic effect Effects 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
239000008266 hair spray Substances 0.000 claims description 3
239000000049 pigment Substances 0.000 claims description 3
239000003755 preservative agent Substances 0.000 claims description 3
239000003380 propellant Substances 0.000 claims description 3
230000001681 protective effect Effects 0.000 claims description 3
239000002453 shampoo Substances 0.000 claims description 3
239000004094 surface-active agent Substances 0.000 claims description 3
230000001680 brushing effect Effects 0.000 claims description 2
239000003906 humectant Substances 0.000 claims description 2
TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 2
USXXCMAXICZZJL-UHFFFAOYSA-N diethyl 2-[methoxy(phenyl)methylidene]propanedioate Chemical compound C(C)OC(C(C(=O)OCC)=C(C1=CC=CC=C1)OC)=O USXXCMAXICZZJL-UHFFFAOYSA-N 0.000 claims 1
230000000475 sunscreen effect Effects 0.000 abstract description 6
239000000516 sunscreening agent Substances 0.000 abstract description 6
125000003545 alkoxy group Chemical group 0.000 abstract description 2
125000000217 alkyl group Chemical group 0.000 abstract description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
235000019198 oils Nutrition 0.000 description 20
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
239000002904 solvent Substances 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
235000014113 dietary fatty acids Nutrition 0.000 description 9
239000000194 fatty acid Substances 0.000 description 9
229930195729 fatty acid Natural products 0.000 description 9
238000002360 preparation method Methods 0.000 description 9
150000001299 aldehydes Chemical class 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000012071 phase Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000005457 ice water Substances 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
238000001228 spectrum Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
150000003934 aromatic aldehydes Chemical class 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000000921 elemental analysis Methods 0.000 description 4
LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
150000004665 fatty acids Chemical class 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
238000002211 ultraviolet spectrum Methods 0.000 description 4
KBXMYFVAWMPGAT-UHFFFAOYSA-N 4-methoxy-3-prop-2-enylbenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1CC=C KBXMYFVAWMPGAT-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
235000019502 Orange oil Nutrition 0.000 description 3
239000000470 constituent Substances 0.000 description 3
239000006071 cream Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000002844 melting Methods 0.000 description 3
239000010502 orange oil Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
238000005406 washing Methods 0.000 description 3
IJGXTTPJTDSRBO-UHFFFAOYSA-N 4-hydroxy-3-methoxy-5-prop-2-enylbenzaldehyde Chemical compound COC1=CC(C=O)=CC(CC=C)=C1O IJGXTTPJTDSRBO-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
230000009471 action Effects 0.000 description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
150000008041 alkali metal carbonates Chemical class 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
239000003480 eluent Substances 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
235000013336 milk Nutrition 0.000 description 2
239000008267 milk Substances 0.000 description 2
210000004080 milk Anatomy 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000000843 powder Substances 0.000 description 2
230000008569 process Effects 0.000 description 2
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
0 *c(cc1)cc(*=C)c1ON Chemical compound *c(cc1)cc(*=C)c1ON 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
BCINBJDCXBFCDT-UHFFFAOYSA-N 1-methoxy-2-prop-2-enylbenzene Chemical compound COC1=CC=CC=C1CC=C BCINBJDCXBFCDT-UHFFFAOYSA-N 0.000 description 1
QIRNGVVZBINFMX-UHFFFAOYSA-N 2-allylphenol Chemical compound OC1=CC=CC=C1CC=C QIRNGVVZBINFMX-UHFFFAOYSA-N 0.000 description 1
FBLUJEZNJVZMKK-UHFFFAOYSA-N 3,4-dimethoxy-5-prop-2-enylbenzaldehyde Chemical compound COC1=CC(C=O)=CC(CC=C)=C1OC FBLUJEZNJVZMKK-UHFFFAOYSA-N 0.000 description 1
DGWCHURQYFMBFC-UHFFFAOYSA-N 3-methoxy-4-prop-2-enoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC=C1OCC=C DGWCHURQYFMBFC-UHFFFAOYSA-N 0.000 description 1
DUUDAGLUGZXHRC-UHFFFAOYSA-N 4-butoxy-3-methoxy-5-prop-2-enylbenzaldehyde Chemical compound CCCCOC1=C(CC=C)C=C(C=O)C=C1OC DUUDAGLUGZXHRC-UHFFFAOYSA-N 0.000 description 1
HDZJQLIQQWIJBW-UHFFFAOYSA-N 4-hydroxy-3-prop-2-enylbenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1CC=C HDZJQLIQQWIJBW-UHFFFAOYSA-N 0.000 description 1
TYNJQOJWNMZQFZ-UHFFFAOYSA-N 4-prop-2-enoxybenzaldehyde Chemical compound C=CCOC1=CC=C(C=O)C=C1 TYNJQOJWNMZQFZ-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
238000005821 Claisen rearrangement reaction Methods 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
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
206010015150 Erythema Diseases 0.000 description 1
238000006000 Knoevenagel condensation reaction Methods 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
206010063493 Premature ageing Diseases 0.000 description 1
208000032038 Premature aging Diseases 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
230000004075 alteration Effects 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000008901 benefit Effects 0.000 description 1
YSRBRMMHTQOUDW-UHFFFAOYSA-N bis(2-ethylhexyl) propanedioate Chemical compound CCCCC(CC)COC(=O)CC(=O)OCC(CC)CCCC YSRBRMMHTQOUDW-UHFFFAOYSA-N 0.000 description 1
244000309464 bull Species 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000003581 cosmetic carrier Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000003745 detangling effect Effects 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
231100000321 erythema Toxicity 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000004872 foam stabilizing agent Substances 0.000 description 1
150000003948 formamides Chemical class 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
230000022244 formylation Effects 0.000 description 1
238000006170 formylation reaction Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
235000014593 oils and fats Nutrition 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
231100000760 phototoxic Toxicity 0.000 description 1
RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
239000011252 protective cream Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
230000037307 sensitive skin Effects 0.000 description 1
231100000075 skin burn Toxicity 0.000 description 1
230000007928 solubilization Effects 0.000 description 1
238000005063 solubilization Methods 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
239000002966 varnish Substances 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 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
- A61K8/30—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
- 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

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)
Emergency Medicine (AREA)
Birds (AREA)
Epidemiology (AREA)
Dermatology (AREA)
Cosmetics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

LU87271A 1988-07-08 1988-07-08 Nouveaux derives insatures liposolubles des benzalmalonates et leur utilisation en tant qu'absorbeurs du rayonnement ultra-violet en cosmetique LU87271A1 (fr)

Priority Applications (8)

Application Number	Priority Date	Filing Date	Title
LU87271A LU87271A1 (fr)	1988-07-08	1988-07-08	Nouveaux derives insatures liposolubles des benzalmalonates et leur utilisation en tant qu'absorbeurs du rayonnement ultra-violet en cosmetique
DE8989401906T DE68901162D1 (de)	1988-07-08	1989-07-04	Ungesaettigte derivate fettloeslicher benzalmalonate und ihre verwendung als uv-absorber in der kosmetik.
AT89401906T ATE74588T1 (de)	1988-07-08	1989-07-04	Ungesaettigte derivate fettloeslicher benzalmalonate und ihre verwendung als uvabsorber in der kosmetik.
EP89401906A EP0350386B1 (de)	1988-07-08	1989-07-04	Ungesättigte Derivate fettlöslicher Benzalmalonate und ihre Verwendung als UV-Absorber in der Kosmetik
US07/375,820 US5175340A (en)	1988-07-08	1989-07-05	New liposoluble unsaturated benzalmalonate derivatives and their use as absorbers for ultraviolet radiation in cosmetics
BR898903372A BR8903372A (pt)	1988-07-08	1989-07-07	Processo de preparacao de um derivado insaturado de benzalmalonato,composicao cosmetica,processo de protecao e preparacao da mesma
AU37935/89A AU622195B2 (en)	1988-07-08	1989-07-07	New liposoluble unsaturated benzalmalonate derivatives and their use as absorbers for ultraviolet radiation in cosmetics
JP1174336A JP2781415B2 (ja)	1988-07-08	1989-07-07	紫外線吸収剤

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
LU87271A LU87271A1 (fr)	1988-07-08	1988-07-08	Nouveaux derives insatures liposolubles des benzalmalonates et leur utilisation en tant qu'absorbeurs du rayonnement ultra-violet en cosmetique

Publications (1)

Publication Number	Publication Date
LU87271A1 true LU87271A1 (fr)	1990-02-07

Family

ID=19731071

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU87271A LU87271A1 (fr)	1988-07-08	1988-07-08	Nouveaux derives insatures liposolubles des benzalmalonates et leur utilisation en tant qu'absorbeurs du rayonnement ultra-violet en cosmetique

Country Status (8)

Country	Link
US (1)	US5175340A (de)
EP (1)	EP0350386B1 (de)
JP (1)	JP2781415B2 (de)
AT (1)	ATE74588T1 (de)
AU (1)	AU622195B2 (de)
BR (1)	BR8903372A (de)
DE (1)	DE68901162D1 (de)
LU (1)	LU87271A1 (de)

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IL91382A (en) *	1988-09-01	1995-06-29	Orion Yhtymae Oy	Alkenyl or arylmethylene-substituted beta-diketones their preparation and pharmaceutical compositions containing them
GB9110123D0 (en) *	1991-05-10	1991-07-03	Dow Corning	Organosilicon compounds their preparation and use
DE4221740A1 (de) *	1992-07-02	1994-01-05	Merck Patent Gmbh	Benzyliden-chinuclidinone
US5508025A (en) *	1993-12-24	1996-04-16	Kao Corporation	Naphthalenemethylenemalonic diesters, and UV absorbers and cosmetic compositions containing the diesters
FR2757055B1 (fr) *	1996-12-17	1999-02-05	Oreal	Compositions comprenant un derive de dibenzoylmethane, un derive de 1,2,3-triazine et un benzalmalonate de dialkyle et utilisations
US6207740B1 (en)	1999-07-27	2001-03-27	Milliken & Company	Polymeric methine ultraviolet absorbers
JP4687849B2 (ja) *	2001-04-05	2011-05-25	Ｊｘ日鉱日石エネルギー株式会社	高純度ジイソプロピルエーテルおよびその製法
DE60237244D1 (de) *	2001-07-16	2010-09-16	Merck Patent Gmbh	Photostabile organische Sonnenschutzmittel mit antioxidativen Eigenschaften
US6831191B2 (en)	2001-12-20	2004-12-14	Em Industries	Photo stable organic sunscreen compounds with antioxidant properties and compositions obtained therefrom
US6602515B2 (en)	2001-07-16	2003-08-05	Em Industries	Photo stable organic sunscreen compounds with antioxidant properties and compositions obtained therefrom
US6699463B2 (en)	2002-04-10	2004-03-02	Em Industries	Photostable cationic organic sunscreen compounds with antioxidant properties and compositions obtained therefrom
US6936735B2 (en) *	2002-08-27	2005-08-30	Emd Chemicals, Inc.	Photostable cationic organic sunscreen compounds and compositions obtained therefrom
FR2853540B1 (fr) *	2003-04-08	2006-07-07	Oreal	Utilisation cosmetique de nouveaux agents desquamants
US7622448B2 (en)	2003-04-08	2009-11-24	L'oreal	Compositions suitable for topical application to the skin
CN101163659B (zh) *	2005-04-19	2012-09-05	默克专利股份有限公司	抗氧化剂
US20080286217A1 (en) *	2007-05-14	2008-11-20	Chaudhuri Ratan K	Sunscreen compositions and methods
WO2011060099A2 (en)	2009-11-10	2011-05-19	Laboratory Skin Care, Inc.	Sunscreen compositions comprising uniform, rigid, spherical, nanoporous calcium phosphate particles, and methods of making and using the same
US8617528B2 (en)	2010-12-06	2013-12-31	Sytheon Ltd.	Compositions and methods for stabilizing ingredients using 2,4-pentanedione compounds
ES3055661T3 (en)	2016-08-23	2026-02-13	Sytheon Ltd	Compositions comprising isohexide diesters of c18 fatty acids and their use in methods for restoring epidermal integrity and function and treating dermatological diseases
EP4299077A3 (de)	2016-10-31	2024-04-17	Sytheon Limited	Hautverstärkende zusammensetzungen und verfahren
EP3664773A4 (de)	2017-08-11	2021-05-12	Sytheon Limited	Haarbehandlungszusammensetzungen und -verfahren
WO2021112931A1 (en)	2019-12-02	2021-06-10	Sytheon Limited	Compositions comprising meroterpenes and linoleic acid derivatives and their use for regulating the endocannabinoid system

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GB1037169A (en) *	1964-04-23	1966-07-27	American Cyanamid Co	Stabilization of polymers
CH491991A (de) *	1968-10-04	1970-06-15	Bayer Ag	Verwendung von Tetracarbonsäureestern zum Schützen organischer Stoffe gegen UV-Strahlung
US4414393A (en) *	1981-11-05	1983-11-08	Ciba-Geigy Corporation	Ultraviolet-absorbing stabilizers substituted by an aliphatic hydroxyl group
EP0100651A1 (de) *	1982-08-03	1984-02-15	VAN DYK & COMPANY, INC.	Dialkylmalonate als organische Hilfsmittel für Sonnenschutzmittel
US4584133A (en) *	1983-11-07	1986-04-22	Schering Corporation	Process for the production of penems
DE3424066A1 (de) *	1984-06-29	1986-01-09	Bayer Ag, 5090 Leverkusen	Neue benzyliden- oder vinyloge benzylidenmalonsaeurepolyamide und -polyesteramide, ihre herstellung und ihre verwendung zur uv-stabilisierung von kunststoffen

1988
- 1988-07-08 LU LU87271A patent/LU87271A1/fr unknown
1989
- 1989-07-04 EP EP89401906A patent/EP0350386B1/de not_active Expired - Lifetime
- 1989-07-04 DE DE8989401906T patent/DE68901162D1/de not_active Expired - Lifetime
- 1989-07-04 AT AT89401906T patent/ATE74588T1/de not_active IP Right Cessation
- 1989-07-05 US US07/375,820 patent/US5175340A/en not_active Expired - Lifetime
- 1989-07-07 BR BR898903372A patent/BR8903372A/pt unknown
- 1989-07-07 JP JP1174336A patent/JP2781415B2/ja not_active Expired - Fee Related
- 1989-07-07 AU AU37935/89A patent/AU622195B2/en not_active Ceased

Also Published As

Publication number	Publication date
ATE74588T1 (de)	1992-04-15
JP2781415B2 (ja)	1998-07-30
BR8903372A (pt)	1990-02-13
DE68901162D1 (de)	1992-05-14
US5175340A (en)	1992-12-29
JPH0259541A (ja)	1990-02-28
AU622195B2 (en)	1992-04-02
EP0350386B1 (de)	1992-04-08
EP0350386A1 (de)	1990-01-10
AU3793589A (en)	1990-01-11

Publication	Publication Date	Title
EP0350386B1 (de)	1992-04-08	Ungesättigte Derivate fettlöslicher Benzalmalonate und ihre Verwendung als UV-Absorber in der Kosmetik
EP0507691B1 (de)	1995-03-15	S-Triazinderivate mit Benzalmalonaten als Substituenten, Verfahren zu ihrer Herstellung, diese enthaltende kosmetische Zubereitungen mit filternder Wirkung und ihre Verwendung als Schutzmittel für Haut und Haar
EP0392883B1 (de)	1993-04-28	Mit einer Benzotriazolgruppe substituierte Diorganopolysiloxane enthaltende Kosmetika sowie deren Verwendung zum Schutz von Haut und Haaren
EP0507692B1 (de)	1998-03-04	S-Triazinederivate mit Benzylidencampfer als Substituent, Verfahren zu ihrer Herstellung, diese enthaltende kosmetische Zubereitungen mit filtrierender Wirkung und ihre Verwendung als Schutzmittel für Haut und Haar
CA1299581C (fr)	1992-04-28	Composition cosmetique contenant des derives hydroxyles de chalcone et son utilisation pour la protection de la peau et des cheveux contre les radiations lumineuses, nouveaux derives hydroxyles de chalcone utilises et leur procede de preparation
CA1202327A (fr)	1986-03-25	Compositions cosmetiques contenant des derives hydroxy les du dibenzoylmethane et leur utilisation pour la pr otection de l'epiderme humain contre les rayons ultrav iolets, nouveaux derives hydroxyles du dibenzoylmethan e utilises et leur procede de preparation
EP0368717B1 (de)	1993-01-20	Derivate der 5-Benzyliden-3-oxacyclopentanone, ihr Herstellungsverfahren und ihre Verwendung in kosmetischen Zusammensetzungen zum Schutz der Haut und der Haare gegen Sonnenstrahlung
FR2528420A1 (fr)	1983-12-16	Nouveaux 3-benzylidene camphres, leur procede de preparation et leur utilisation pour la protection contre les rayons uv
EP0392882B1 (de)	1992-10-28	Mit einer Benzalmalonatgruppe substituierte Diorganopolysiloxane enthaltende Kosmetika sowie deren Verwendung zum Schutz von Haut und Haaren
FR2725448A1 (fr)	1996-04-12	Nouveaux filtres solaires, compositions cosmetiques photoprotectrices les contenant et utilisations
EP0716089B1 (de)	1997-08-20	Neue Sonnenschutzfilter, diese enthaltende kosmetische Sonnenschutzmittel und deren Verwendungen
EP0335777B1 (de)	1991-12-18	Kosmetische Verwendung von Diorganopolysiloxanen mit 3-Benzyliden-Kampfer als funktioneller Gruppe
FR2717808A1 (fr)	1995-09-29	Composition cosmétique stable à la lumière.
EP0383655B1 (de)	1993-04-28	Verwendung von Diorganopolysiloxanen mit Dibenzoylmethane-Funktion und diese Verbindungen enthaltende Zusammensetzung für den Schutz von Haut und Haar
CH663017A5 (fr)	1987-11-13	Derives du 3-benzylidene camphre, leur procede de preparation et leur utilisation en tant qu'agents de protection contre les rayons uv et en tant que medicaments.
EP0390681B1 (de)	1993-08-25	Kosmetische und pharmazeutische Zusammensetzungen, die lipophile Derivate von Benzylidenkampfer enthalten und lipophile Benzylidenkampfer-Derivate
CH677111A5 (de)	1991-04-15
LU87339A1 (fr)	1990-04-06	Nouveaux derives de benzylidene-cyclanones,leur procede de preparation,leur utilisation en tant qu'agents anti-oxydants et comme filtres solaires,compositions cosmetiques et pharmaceutiques les contenant
JP2612922B2 (ja)	1997-05-21	不飽和３―ベンジリデンカンファー誘導体および化粧品組成物