DE2728242A1 - COSMETIC LIGHT PROTECTION AGENTS FOR THE UV-A AREA - Google Patents
COSMETIC LIGHT PROTECTION AGENTS FOR THE UV-A AREAInfo
- Publication number
- DE2728242A1 DE2728242A1 DE19772728242 DE2728242A DE2728242A1 DE 2728242 A1 DE2728242 A1 DE 2728242A1 DE 19772728242 DE19772728242 DE 19772728242 DE 2728242 A DE2728242 A DE 2728242A DE 2728242 A1 DE2728242 A1 DE 2728242A1
- Authority
- DE
- Germany
- Prior art keywords
- benzylidene
- acid
- cosmetic
- pyruvic acid
- levulinic acid
- 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- Withdrawn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
- 239000002537 cosmetic Substances 0.000 title claims description 20
- 239000011814 protection agent Substances 0.000 title description 10
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims description 30
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 29
- 229940040102 levulinic acid Drugs 0.000 claims description 20
- -1 alkyl radical Chemical class 0.000 claims description 19
- 229940107700 pyruvic acid Drugs 0.000 claims description 15
- 239000007859 condensation product Substances 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 7
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- 230000000475 sunscreen effect Effects 0.000 claims description 5
- 239000000516 sunscreening agent Substances 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 239000004611 light stabiliser Substances 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 claims description 3
- 229960000458 allantoin Drugs 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 150000005840 aryl radicals Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000003672 ureas Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 7
- 210000003491 skin Anatomy 0.000 description 7
- YQEMORVAKMFKLG-UHFFFAOYSA-N 2-stearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 6
- 239000006071 cream Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 230000037072 sun protection Effects 0.000 description 5
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- 235000013871 bee wax Nutrition 0.000 description 4
- 239000012166 beeswax Substances 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 239000006210 lotion Substances 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000003380 propellant Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- YQOUMBVFEWZLME-UHFFFAOYSA-N 2-oxo-4-phenylbut-3-enoic acid Chemical compound OC(=O)C(=O)C=CC1=CC=CC=C1 YQOUMBVFEWZLME-UHFFFAOYSA-N 0.000 description 3
- 206010042496 Sunburn Diseases 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- HXBHTZSDWPPLKO-KBXRYBNXSA-N (3e,5e)-2-oxo-6-phenylhexa-3,5-dienoic acid Chemical compound OC(=O)C(=O)\C=C\C=C\C1=CC=CC=C1 HXBHTZSDWPPLKO-KBXRYBNXSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- RIEKEURCMFJFTJ-UHFFFAOYSA-N 2-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxopentanoic acid Chemical compound COC=1C=C(C=C(C(=O)O)CC(=O)C)C=CC=1O RIEKEURCMFJFTJ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 2
- HSHNITRMYYLLCV-UHFFFAOYSA-N 4-methylumbelliferone Chemical compound C1=C(O)C=CC2=C1OC(=O)C=C2C HSHNITRMYYLLCV-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 239000005662 Paraffin oil Substances 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 229910021538 borax Inorganic materials 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- JMVAUHRMKRGQEX-UHFFFAOYSA-N ethyl 2-[(3,4-dimethoxyphenyl)methylidene]-4-oxopentanoate Chemical compound CCOC(=O)C(CC(C)=O)=CC1=CC=C(OC)C(OC)=C1 JMVAUHRMKRGQEX-UHFFFAOYSA-N 0.000 description 2
- JROXCHHVHPOBHU-UHFFFAOYSA-N ethyl 2-oxo-4-phenylbut-3-enoate Chemical compound CCOC(=O)C(=O)C=CC1=CC=CC=C1 JROXCHHVHPOBHU-UHFFFAOYSA-N 0.000 description 2
- AUJRZEZHLMYJNS-UHFFFAOYSA-N ethyl 2-oxo-6-phenylhexa-3,5-dienoate Chemical compound CCOC(=O)C(=O)C=CC=CC1=CC=CC=C1 AUJRZEZHLMYJNS-UHFFFAOYSA-N 0.000 description 2
- HBYTXDNOXLIKOK-UHFFFAOYSA-N ethyl 4-(4-methoxyphenyl)-2-oxobut-3-enoate Chemical compound CCOC(=O)C(=O)C=CC1=CC=C(OC)C=C1 HBYTXDNOXLIKOK-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 239000000787 lecithin Substances 0.000 description 2
- 229940067606 lecithin Drugs 0.000 description 2
- 235000010445 lecithin Nutrition 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 235000008390 olive oil Nutrition 0.000 description 2
- 239000004006 olive oil Substances 0.000 description 2
- 235000019271 petrolatum Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 229940076788 pyruvate Drugs 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000004328 sodium tetraborate Substances 0.000 description 2
- 235000010339 sodium tetraborate Nutrition 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- DSEKYWAQQVUQTP-XEWMWGOFSA-N (2r,4r,4as,6as,6as,6br,8ar,12ar,14as,14bs)-2-hydroxy-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1h-picen-3-one Chemical compound C([C@H]1[C@]2(C)CC[C@@]34C)C(C)(C)CC[C@]1(C)CC[C@]2(C)[C@H]4CC[C@@]1(C)[C@H]3C[C@@H](O)C(=O)[C@@H]1C DSEKYWAQQVUQTP-XEWMWGOFSA-N 0.000 description 1
- PORJGOYPXCWSQM-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylmethylidene)-4-oxopentanoic acid Chemical compound C1OC=2C=C(C=C(C(=O)O)CC(=O)C)C=CC=2O1 PORJGOYPXCWSQM-UHFFFAOYSA-N 0.000 description 1
- PDUWINKIRPQLBQ-UHFFFAOYSA-N 2-[(3,4-dimethoxyphenyl)methylidene]-4-oxopentanoic acid Chemical compound COC=1C=C(C=C(C(=O)O)CC(=O)C)C=CC=1OC PDUWINKIRPQLBQ-UHFFFAOYSA-N 0.000 description 1
- 239000004808 2-ethylhexylester Substances 0.000 description 1
- ACCWCWKIASBEKV-UHFFFAOYSA-N 3-benzylideneheptan-2-one Chemical compound CCCCC(C(C)=O)=CC1=CC=CC=C1 ACCWCWKIASBEKV-UHFFFAOYSA-N 0.000 description 1
- SHVBLFWLPMOIIO-UHFFFAOYSA-N 4-(4-methoxyphenyl)-2-oxobut-3-enoic acid Chemical compound COC1=CC=C(C=CC(=O)C(O)=O)C=C1 SHVBLFWLPMOIIO-UHFFFAOYSA-N 0.000 description 1
- CJIJXIFQYOPWTF-UHFFFAOYSA-N 7-hydroxycoumarin Natural products O1C(=O)C=CC2=CC(O)=CC=C21 CJIJXIFQYOPWTF-UHFFFAOYSA-N 0.000 description 1
- 206010004146 Basal cell carcinoma Diseases 0.000 description 1
- 206010015150 Erythema Diseases 0.000 description 1
- 208000001126 Keratosis Diseases 0.000 description 1
- 241000195947 Lycopodium Species 0.000 description 1
- JJGYXGYYMSOVCS-UHFFFAOYSA-N NC1=NC(N)=NC(N)=N1.OC(=O)C1=CC=CC=C1O Chemical compound NC1=NC(N)=NC(N)=N1.OC(=O)C1=CC=CC=C1O JJGYXGYYMSOVCS-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- WYWZRNAHINYAEF-UHFFFAOYSA-N Padimate O Chemical compound CCCCC(CC)COC(=O)C1=CC=C(N(C)C)C=C1 WYWZRNAHINYAEF-UHFFFAOYSA-N 0.000 description 1
- 206010051246 Photodermatosis Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 1
- 208000000453 Skin Neoplasms Diseases 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- QNHQEUFMIKRNTB-UHFFFAOYSA-N aesculetin Natural products C1CC(=O)OC2=C1C=C(O)C(O)=C2 QNHQEUFMIKRNTB-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- IAEGSOXREPIJPL-UHFFFAOYSA-N butyl 2-[[4-(dimethylamino)phenyl]methylidene]-4-oxopentanoate Chemical compound C(CCC)OC(C(CC(=O)C)=CC1=CC=C(C=C1)N(C)C)=O IAEGSOXREPIJPL-UHFFFAOYSA-N 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 231100000762 chronic effect Toxicity 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- UVCJGUGAGLDPAA-UHFFFAOYSA-N ensulizole Chemical compound N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 UVCJGUGAGLDPAA-UHFFFAOYSA-N 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 231100000321 erythema Toxicity 0.000 description 1
- ILEDWLMCKZNDJK-UHFFFAOYSA-N esculetin Chemical compound C1=CC(=O)OC2=C1C=C(O)C(O)=C2 ILEDWLMCKZNDJK-UHFFFAOYSA-N 0.000 description 1
- XPKFLEVLLPKCIW-UHFFFAOYSA-N ethyl 4-(diethylamino)benzoate Chemical compound CCOC(=O)C1=CC=C(N(CC)CC)C=C1 XPKFLEVLLPKCIW-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Substances OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- ZWDYRZGSCHGREX-UHFFFAOYSA-N methyl 2-oxo-4-phenylbut-3-enoate Chemical compound COC(=O)C(=O)C=CC1=CC=CC=C1 ZWDYRZGSCHGREX-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- VJXOEQBGNNPWMQ-UHFFFAOYSA-N propan-2-yl 3-(4-acetamidophenyl)prop-2-enoate Chemical compound CC(C)OC(=O)C=CC1=CC=C(NC(C)=O)C=C1 VJXOEQBGNNPWMQ-UHFFFAOYSA-N 0.000 description 1
- 150000004717 pyruvic acids Chemical class 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 230000037380 skin damage Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
- ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical compound C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 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
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
-
- 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
Description
Henkel KGaAHenkel KGaA
ie und Literatur - 3 - li 5612ie and literature - 3 - li 5612
Kosmetische Lichtschutzmittel für den TJV-A-!leroicliCosmetic light protection agents for the TJV-A-! Leroicli
Gegenstand der Erfindung sind kosmetische Lichtschutzmittel für den UV-A-Bereich mit einem Gehalt ιχτι BronztvaubensMure- bzw. Lävulinsäurekondensationsprodukton, die bei topischer Anwendung auf der Haut einen Schutz vor den schädigenden Einflüssen des längorwelligen UV-A-Anteils des Sonnenlicht« bei längerer Einwirkung gewähren. The invention relates to cosmetic light protection agents for the UV-A range with a content ιχτι BronztvaubensMure- or levulinic acid condensation product which, when applied topically to the skin, provide protection against the harmful effects of the long-wave UV-A component of sunlight during prolonged exposure .
Die allgemein als kosmetische Sonnenschutzmittel bzw. Lichtschutzmittel benutzten Präparationen ent.ha3.ten zur Verhinderung des Sonnenbrandes Bestandteile, die den kurzwelligen UV-B-Anteil des Sonnenlichts absorbieren bzw. reflektieren. Sie setzen die Dosis an kurzwelliger Strahlung, die die äußeren Schichten der Haut durchdringt, herab und verhindern damit die Ausbildung schwerer Erytheme, ohne daß die durch den längex-welligen Anteil verursachte Bräunung unterbunden wird. Dieser längerwellige Anteil des Sonnenlichts, der etwa den Bereich von 320 - *IOO nm umfaßt, ermöglicht aber nicht nur die angenehme Bräunung der Haut, sondern wird auch für die chronisch lichtgeschädigte Haut verantwortlich gemacht. Diese Schädigungen wurden früher als altersbedingt angesehen, man sprach allgemein von der Altershaut. Heute weiß man jedoch, daß sie im wesentlichen von der Gesamtdauer und Stärke der Lichteinwii-kung abhängen. Derartige HautSchädigungen machen sich durch eine erhöhte Faltenbildung der Haut infolge Elastizitätsverlust, durch eine Verdünnung der Oberhaut, eine Gelbbraunfärbung der Gesichtshaut, Pigmentverschiebungen und schließlich durch Keratosen bemerkbar, die zu Krebsvorstufen und Hautkrebserkrankungen wie Spinaliomen und Basaliomen führen können. The preparations generally used as cosmetic sunscreens or light stabilizers contain, to prevent sunburn, components that absorb or reflect the short-wave UV-B component of sunlight. They reduce the dose of short-wave radiation that penetrates the outer layers of the skin and thus prevent the formation of severe erythema without the tanning caused by the long-wave portion being suppressed. This longer-wave portion of the sunlight, which covers approximately the range from 320 to 100 nm, not only enables the skin to be tanned comfortably, but is also held responsible for the chronically photodamaged skin . In the past, this type of damage was considered to be age-related; it was generally referred to as aging skin. Today we know , however, that they essentially depend on the total duration and strength of the exposure to light. Skin damage of this kind becomes noticeable through increased wrinkling of the skin as a result of loss of elasticity, thinning of the epidermis, yellow-brown discoloration of the facial skin, pigment shifts and finally through keratoses, which can lead to cancer precursors and skin cancers such as spinaliomas and basal cell carcinomas.
Es besteht daher nicht nur aus rein ästhetischen Gesichtspunkten ein Bedarf nach kosmetischen Mitteln, die die schäd-There is therefore not only from a purely aesthetic point of view a need for cosmetic agents that
•09882/011?• 09882/011?
Henkel KQaA Patente und LiteraturHenkel KQaA patents and literature
- k - D 56I2 - k - D 56I2
liehen Nebenwirkungen einer zu langen und intensiven Einwirkung des längorwelligen UV-A-Anteils des Sonnenlichts unterbinden. Die Mittel müssen darüber hinaus toxikologisch und dermatologisch unbedenklich sein, eine gute Licht- und Wärmestabilität aufweisen und gut auf der Haut haften·borrowed side effects of too long and intense exposure the long-wave UV-A component of sunlight. The funds must also be toxicologically and be dermatologically harmless, have good light and heat stability and adhere well to the skin
Es wurde nun gefunden, daß kosmetische Lichtschutzmittel mit einem Gehalt an Brenztraubensäure- bzw* Lävulinsäurekondensationsprodukten dor allgemeinen FormelIt has now been found that cosmetic light stabilizers with a content of pyruvic acid or levulinic acid condensation products dor general formula
0
R - CH = CH - C - (CH2)n - COOR1 0
R - CH = CH - C - (CH 2 ) n - COOR 1
in der η die Zahlen 0 oder 2, R1 Wasserstoff, einen Alkylrest mit 1 - fr Kohlenstoffatomen oder ein salzbildendes Kation aus der Gruppe der Alkali- oder Erdalkalimetalle, des Ammonium- oder substituierten Ammoniumkations, des gegebenenfalls alkylsubstituierten Harnstoffs oder des Allantoins und R die Reste Ar oder -CH=CH-Ar bedeuten, wobei Ar einen Arylrest, insbesondere einen Phenylrest, der gegebenenfalls durch einen oder mehrere C1-C^-Alkylreste, eine oder mehrere Hydroxylgruppen, eine oder mehrere C1-C^-Alkoxygruppen, eine-oder mehrere Amino- bzw« Di-(C1-Cl)-alkylaminogruppen, ein oder mehrere Halogenatome oder eine Methylendioxygruppe substituiert sein kann, darstellt, die gestellten Anforderungen veitgehend erfüllen.in which η the numbers 0 or 2, R 1 is hydrogen, an alkyl radical with 1 - for carbon atoms or a salt-forming cation from the group of alkali or alkaline earth metals, the ammonium or substituted ammonium cation, the optionally alkyl-substituted urea or the allantoin and R the Rests Ar or -CH = CH-Ar, where Ar is an aryl radical, in particular a phenyl radical, which is optionally substituted by one or more C 1 -C ^ -alkyl radicals, one or more hydroxyl groups, one or more C 1 -C ^ -alkoxy groups, one or more amino or «di (C 1 -Cl) -alkylamino groups, one or more halogen atoms or a methylenedioxy group can be substituted, which largely meet the requirements.
Bei den in den erfinduhgsgemäßen kosmetischen LichtSchutzmitteln einzusetzenden Brenztraubensäure- bzw« Lävulinsäurekondensationeprodukten handelt es eich um literaturbekannte Präparate, deren Herstellung von E.D. Stecher und H,F. Ryder im J.Am.Chem.Soc. 7fr. S. 4392 ff. (1952) beziehungsweise von S.H. Zaheer, J.K. Kacker und N. Shanmukha Rao in Chem.Ber. J39_, S. 35fr ff« (1956) eingehend beschrieben wird.The pyruvic acid or levulinic acid condensation products to be used in the cosmetic light protection agents according to the invention are preparations known from the literature, the manufacture of which by ED Stecher and H, F. Ryder in the J.Am.Chem.Soc. 7fr . S. 4392 ff. (1952) or by SH Zaheer, JK Kacker and N. Shanmukha Rao in Chem.Ber. J39_, p. 35fr ff "(1956) is described in detail.
•09882/0117• 09882/0117
Henkel KGaA Patente und LiteraturHenkel KGaA patents and literature
- 5 - D 5612- 5 - D 5612
Als Brenztraubensäure- bzw, Lävulinsäurekondensationsprodukte, die in den erfindungsgemäßen kosmetischen LichtSchutzmitteln eingesetzt werden können, sind z.B. Benzylidenbrenztraubensäure, Benzylidenbrenztraubensäuremethyloster, Benzylidenbrenztraubensäureäthylester, Benzylidenbrenztraubensäurebutylester, Jf-Hydroxy-benzyliden-brenztraubensäure, 3»^- Dihydroxy—benzyliden-brenztraubensäuremethylester, h-Mothoxybenzyliden-brenztraubensäuro, 3» 4-Dimethoxy-benzyliden-brenztraubensäuremethylester, 4-Methoxy-benzyliden-brenztraubensäureäthylester, ii-Chlor-benzyliden-brenztraubensäure, 3»^— Dichlorbenzyliden-brenztraubensäure, 4-Amino-benzylidenbrenztraubensäuremethylester, U-Dimethylamino-benzylidenbrenztraubensäureäthylester, 3» 4-Methylendioxy-benzylidenbrenztraubensäure, Cinnamyliden-brenztraubensäure, Cinnamylidenbrenztraubensäureäthylester, Benzylidenlävulinsäure, Benzylidenlävulinsäuremethylester, Benzylidenlävulinsäureäthylester, Benzylidenlävulinsäure-isopropylester, Benzylidenlävulinsäurebutylester, 4-Hydroxy-benzyliden-lävulinsäurebutylester, 3»^—Dihydroxy-benzyliden-lävulinsäure, 4-Methoxy—benzylidenlävulineäure, Jf-Methoxy-benzyliden-lävulinsäurebutylester, 3t4-Dimethoxy-benzyliden-lävulinsäure, 3f^-Dimethoxy-benzylidenlävulinsäureäthylester, 3-Methoxy-U-hydroxy->-benzylidenlävulinsäure, ^-Chlor-benzyliden-lävulinsäuremethylester, 3, ^-DicbJLor-benzyliden-lävulinsäure, 4-Amino-benzylidenlävulinsäuremethylester, ^-Dimethylaroino-benzyliden-lävulinsäuret ^-Dimethylamino-benzyliden-lävulinsäurebutylester, 3,U-Methylendioxy-benzyliden-lävulinsäure sowie die Natrium-, Kalium-, Ammonium-, Äthylammonium-, Xthanolammonium-, Triäthanolammonium-, Harnstoff-, Diäthylharnstoff- und Allantoin- salze der substituierten Brenztraubensäuren und Lävulinsäuren zu nennen· Pyruvic acid or levulinic acid condensation products that can be used in the cosmetic light protection agents according to the invention are, for example, benzylidene pyruvic acid, benzylidene pyruvic acid methyl ester, benzylidene pyruvic acid ethyl ester, benzylidene pyruvic acid ethyl ester, benzylidene pyruvic acid butyl methyl ester, benzylidene pyruvic acid, 3-benzylidene-oxy-butyl-benzylbenzoxy-3 - benzoylbenzoxy-butyl ester, Pyruvic acid, 3 »4-dimethoxy-benzylidene-pyruvic acid methyl ester, 4-methoxy-benzylidene-pyruvic acid ethyl ester, ii-chlorobenzylidene-pyruvic acid, 3» ^ - dichlorobenzylidene-pyruvic acid, 4-aminobenzylidene-pyruvate, 3-aminobenzylidene-pyruvate 4-methylenedioxy-benzylidene pyruvic acid, cinnamylidene pyruvic acid, cinnamylidene pyruvic acid ethyl ester, benzylidene levulinic acid, benzylidene levulinic acid methyl ester, benzylidene levulinic acid ethyl ester, benzylidene levulinic acid isopropyl ester, benzylidene levulinic acid insäurebutylester, 4-hydroxy-benzylidene-lävulinsäurebutylester, 3 »^ - dihydroxy-benzylidene-levulinic acid, 4-methoxy-benzylidenlävulineäure, Jf-methoxy-benzylidene-lävulinsäurebutylester, t 3 4-Dimethoxy-benzylidene-levulinic acid, 3 ^ dimethoxy f benzylidenlävulinsäureäthylester, 3-methoxy-U-hydroxy -> - benzylidenlävulinsäure, ^ -chloro-benzylidenlävulinsäuremethylester, 3, ^ -DicbJLor-benzylidenlävulinsäure, 4-amino-benzylidenlävulinsäuremethylester, ^ -Dimethylaroino-benzylidenlävulinsäure t ^ -Dimethylamino- benzylidene-lävulinsäurebutylester, 3, U-methylenedioxy-benzylidene-levulinic acid and the sodium, potassium, ammonium, Äthylammonium-, Xthanolammonium-, Triäthanolammonium-, urea, allantoin Diäthylharnstoff- and salts of the substituted pyruvic acids and Lävulinsäuren to name ·
Bei ihrem Einsatz in kosmetischen LichtSchutzmitteln können die erfindungsgemäß zu verwendenden Brenztraubensäure- bzw. When used in cosmetic light protection agents, the pyruvic acid or pyruvic acid compounds to be used according to the invention can be used.
•09882/011?• 09882/011?
Henke! KQaA Patente und Literatur - 6 - D 5612Hang! KQaA Patents and Literature - 6 - D 5612
Lävulinsäurekondensationsprodukte in flüssige, pastöse oder feste kosmetische Zubereitungen eingearbeitet werden, vie z.B. wäßrige Suspensionen, Emulsionen, Lösungen in organischen Lösungsmitteln, Ölen, Salben, Cremes, Stifte oder Puder. Bei diesem Einsatz als Lichtschutzmittel gegen die längerwellige UV-A-Strahlung werden die Brenztraubensäure- bzw, Lävulinsäurekondensationsprodukte in Mengen von 0,5 bis 20 Gewichtsprozent, vorzugsweise 2 bis 10 Gewichtsprozent, bezogen auf das gesamte kosmetische Mittel, verwendet»Levulinic acid condensation products in liquid, pasty or solid cosmetic preparations are incorporated, vie e.g. aqueous suspensions, emulsions, solutions in organic solvents, oils, ointments, creams, pens or powders. When used as a light protection agent against the longer-wave UV-A radiation, the pyruvic acid or Levulinic acid condensation products in amounts from 0.5 to 20 Percent by weight, preferably 2 to 10 percent by weight, based on the total cosmetic agent used »
Neben dem alleinigen Einsatz in kosmetischen Lichtschutzmitteln wird der gemeinsame Einsatz mit üblichen UV-B-Filtersubstanzen, die zur Verhütung des Sonnenbrandes dienen, im Vordergrund der Verwendung stehen. Bei diesem Einsatz werden die erfindungsgemäß zu verwendenden Brenztraubensäure- bzw. Lävulinsäurekondensationsprodukte in Kombination mit üblichen UV-B-Filtersubstanzen benutzt, wie zum Beispiel p-Aminobenzoesäureäthylester, -propylester, -butylester, -isobutyleater, -monoglyc erinest er, p-Dirnethylaminobenzoesäureäthylester, -amylester, p-Diäthylaminobenzoesäureäthylester, -amylestor, Salicylsäurementhylester, -homomenthylester, -äthylenglykol— ester, -glycerinester, -2-äthylhexylester, -tert.butylester, -bornylester, -phenylester, Triäthanolammoniumsalz der Salicylsäure, Anthranilsäurementhylester, -bornylester, p-Methoxyzimtsäure-3-äthoxyäthylester, -2-äthylhexylester, p-Acetamidozimtsäure-isopropylester, 2,2'-Dihydroxy-4,k'-dimethoxybenzophenon, 2-Hydroxy-4-methoxybenzophenon, 2-Hydroxy— 4-n-octoxy-benzophenon, 4-Phenylbenzophenon, 2-Hydroxy-U— methoxy-benzophenon-5-sulfonsäure, 4-Phenylbenzophenon-2-carbonsäure-isooctylester, 7-Äthylamino-^-methylcun>arin, 7»8-Dihydroxycumarin, 6,7-Dihydroxycumarin, 7-Hydroxycumarin, 4-Methyl-7-hydr oxy cumarin, 2-Phenylbenzimidazol-5-eulfoneäure, Natrium-3,U-diroethoxyphenylglyoxylat, Butylbenzalaceton, Benzalacetophenon, 3-Benzyliden-D,L-campher, 3-(p-M*thylbenzyliden)-D,L-campher und Urocanineäure.In addition to the sole use in cosmetic sun protection agents, the joint use with conventional UV-B filter substances, which serve to prevent sunburn, will be in the foreground of use. In this application, the pyruvic acid or levulinic acid condensation products to be used according to the invention are used in combination with customary UV-B filter substances, such as ethyl p-aminobenzoate, propyl ester, butyl ester, isobutyl ester, monoglyc erine ester, p-dirnethylaminobenzoate amyl ester, p-diethylaminobenzoic acid ethyl ester, -amyl ester, salicylic acid melamine, -homomenthyl ester, -ethylene glycol ester, -glycerol ester, -2-ethylhexyl ester, -tert-butyl ester, -bornyl ester, -phenyl ester, triethanolammonium salt of salicyl-oxyate, triethanolammonium salt -3-äthoxyäthylester, -2-ethylhexyl, p-acetamidocinnamic acid isopropyl ester, 2,2'-dihydroxy-4, k '-dimethoxybenzophenon, 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-n-octoxy-benzophenone, 4-phenylbenzophenone, 2-hydroxy-U-methoxy-benzophenone-5-sulfonic acid, 4-phenylbenzophenone-2-carboxylic acid isooctyl ester, 7-ethylamino- ^ - methylcunarine, 7-8-dihydroxycoumarin , 6,7-dihydroxycoumarin, 7-hydroxycoumarin, 4-methyl-7-hydroxycoumarin, 2-phenylbenzimidazole-5-sulfonic acid, sodium 3, U-diroethoxyphenylglyoxylate, butylbenzalacetone, benzalacetophenone, 3-benzylidene-D, L-campherone , 3- (pM * thylbenzylidene) -D, L-camphor and urocaninic acid.
§09182/0117§09182 / 0117
Henkel KGaA Patente und LiteraturHenkel KGaA patents and literature
- 7 - D 5612- 7 - D 5612
Die Menge der UV-B-Filtersubstanzen beträgt in diesen auf einer Kombination von UV-A- und UV-B-Schutzsubstanzen basierenden Produkten 1 bis 10 Gewichtsprozent, vorzuf^veise 2 bis 6 Gewichtsprozent, bezogen auf das gesamte kosmetische Lichtschutzmittel. The amount of UV-B filter substances in these is based on a combination of UV-A and UV-B protective substances Products 1 to 10 percent by weight, preferably 2 to 6 Percentage by weight, based on the total cosmetic light protection agent.
Derartige Sonnenschutzmittel verleihen bei topi3cher Anwendung nicht nur einen wirksamen Schutz gegen den gefürchteten Sonnenbrand, sondern auch gegen die chronischen Auswirkungen länger dauernder Einflüsse der längerwelligen UV-A-Anteile des Sonnenlichts. When applied topically, such sunscreens not only provide effective protection against the dreaded sunburn, but also against the chronic effects of longer-lasting influences of the longer-wave UV-A components of sunlight.
Die nachfolgenden Beispiele sollen den Gegenstand der Erfindung näher erläutern, ohne ihn jedoch hierauf zu beschränken.The following examples are intended to explain the subject matter of the invention in more detail without, however, restricting it thereto.
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D 5612D 5612
Die nachfolgenden Beispiele sollen die schützenden Eigenschaften der erfindungsgemäß zu verwendenden Brenztraubensäure« bzw« Lävulinsäurekondensationsprodukte sowie deren Eignung für den Einsatz in kosmetischen LichtSchutzmitteln aufzeigen.The following examples are intended to demonstrate the protective properties of the pyruvic acid to be used according to the invention. or «Levulinic acid condensation products and their suitability for use in cosmetic light protection agents.
In der folgenden Tabelle 1 sind neben der Bezeichnung der Produkte deren Absorptionskennwerte aufgeführt.In the following table 1, in addition to the designation of the Products with their absorption values listed.
(nm)(nm)
säure3,4-methylenedioxy-benzylidene-pyruvette-
acid
äthylester4-methoxy-benzylidene pyruvic acid
ethyl ester
äthylester3,4-dimethoxy-benzylidene-levulinic acid
ethyl ester
butylester4-dimethylamino-benzylidene-levulinic acid
butyl ester
•01182/0117• 01182/0117
Henkel KGaA Patente und LiteraturHenkel KGaA patents and literature
- 9 - D .5612- 9 - D .5612
Nachfolgend werden einige Beispiele für erfindungsgemäße kosmetische Lichtschutzmittel mit einem Gehalt an Brenztraubensäure- bzw* Lävulinsäurekondensationsprodukten aufgeführt :Below are some examples of cosmetic sunscreens according to the invention with a content of pyruvic acid or * levulinic acid condensation products listed :
1« Zur Herstellung eines Lichtschutzöls werden1 «To be used in the production of a light protection oil
80 g ^-Methoxy-bonzyliden-brenztraubensäureäthylester80 g ^ -Methoxy-bonzyliden-pyruvic acid ethyl ester
unter Erwärmen feinst in 100 g Paraffinöl suspendiert, und danach wird bei ca. 25°C mit den folgenden weiteren Bestandteilensuspended under heating in 100 g of paraffin oil, and then at about 25 ° C with the following further Components
300 g lecithinhaltiges Pflanzenöl 400 g Olivenöl300 g vegetable oil containing lecithin 400 g of olive oil
100 g Isopropylmyristat100 g of isopropyl myristate
100 g Purcellinöl100 g purcellin oil
innigst vermischt,intimately mixed,
2« Zur Herstellung eines Lichtschutzpudere werden2 «To be used in the production of a light protection powder
150 g Cinnamylidenbrenztraubensäureäthylester In einem Pulverini sehgerät intensiv mit150 g of ethyl cinnamylidene pyruvate Intensive with a Pulverini vision device
350 g Reisstärke
350 g kolloidalem Ton
100 g Lycopodium
100 g Talkum350 g rice starch
350 g colloidal clay
100 g Lycopodium
100 g talc
In homogene Verteilung gebracht·Brought into homogeneous distribution
3· Zur Herstellung einer Lichtschutzcreme werden3 · To be used in the manufacture of a sun protection cream
kÖ g Glycerinmonostearat
I60 g Bienenwachs
420 g Mineralöl kÖ g glycerine monostearate
I60 g of beeswax
420 g of mineral oil
50 g Cereβin50 g of cereβin
50 g einer Absorptionsbase au*f Basis von50 g of an absorption base based on
- 10 -- 10 -
•08882/0117• 08882/0117
Henkol KGaA Patente und LiteraturHenkol KGaA patents and literature
- 10 - D 5612- 10 - D 5612
Cholesterin, Bienenwachs, Stearylalkohol
und Vaseline
90 g 3»^-Methylendioxy-benzyliden-lävulinsäureCholesterol, beeswax, stearyl alcohol and petroleum jelly
90 g of 3 »^ - methylenedioxy-benzylidene-levulinic acid
bei 65 C zusammengeschmolzen. In diese warme Mischung wird ein auf die gleiche Temperatur erwärmtes Gemisch vonmelted together at 65 C. In this warm mixture will be a mixture of heated to the same temperature
g Wasser
13 g Borax
2 g p-Oxybenzoesäuremethylester g of water
13 g borax
2 g of methyl p-oxybenzoate
unter starkem Rühren eingearbeitet, und die erhaltene Creme wird bis zum Erreichen der Raumtemperatur weiter geführt.incorporated with vigorous stirring and the cream obtained is continued until reaching room temperature.
k» Zur Herstellung einer Lichtschutzemulsion wird in ein auf ca· 80 C erwärmtes Gemisch von k »To produce a sunscreen emulsion is in a heated to about 80 · C mixture of
20 g Glycerinmonostearat 20 g glycerol monostearate
70 g Stearinsäure70 grams of stearic acid
30 g Ölsäure30 g oleic acid
20 g Cetylalkohol20 g of cetyl alcohol
80 g 3,4-Dimethoxy-benzyliden-lävulinsäureäthylester80 g of ethyl 3,4-dimethoxy-benzylidene-levulinate
unter heftigem Rühren eine Mischung von 800 g Wasser, 10g Glycerin und 9 B Triäthanolamin gegeben, Anschliessend wird die erhaltene Lotion kalt gerührt·a mixture of 800 g water, 10 g glycerine and 9 B triethanolamine is added with vigorous stirring, then the resulting lotion is stirred cold.
Vorstehende Emulsion läßt sich auch unter Mitverwendung eines Treibgases im Verhältnis 80 Teile Lotion 1 20 Teilen Treibgas in Aerosolform verpacken. The above emulsion can also be packaged in aerosol form using a propellant in a ratio of 80 parts of lotion to 20 parts of propellant.
5· Zur Herstellung eines SonnenschutztiIs werden5 · To make a sun protection table
80 g 3>^-Methylendioxy-benzYliden-brenstraubenellure kO g p-Methoxyziratsäure-a-äthylhexylester80 g 3> ^ - methylenedioxy-benzYlidene-brenstraubenellure kO g p-Methoxyziratsäure-a-ethylhexylester
unter Erwärmen feinst in 100 g Paraffinöl suspendiertf finely suspended in 100 g paraffin oil while warming f und danach wiiand then wii
und danach wird bei ca, 25°0 Mit den folgenden weiteren and then at approx. 25 ° 0 with the following further
-It--It-
•09882/0119• 09882/0119
Henkel KQaA Patente und Literatur - 11 - D 5612Henkel KQaA patents and literature - 11 - D 5612
g lecithinhaltiges Pflanzenöl g Olivenölg vegetable oil containing lecithin g olive oil
10Og Isopropylmyristat10Og isopropyl myristate
g Purcellinöig purcellin oil
innigst vermischt.intimately mixed.
6, Zur Herstellung einer Sonnenschutzcreme werden6, To be used in the manufacture of a sun protection cream
kO g Glycerinmonostearat
g Bienenwachs
g Mineralöl
50 g Ceresin
50 g einer Absorptionsbaee auf Basis von kO g glycerine monostearate
g beeswax
g mineral oil
50 grams of ceresin
50 g of an absorption baee based on
Cholesterin, Bienenwachs, Stearylalkohol und VaselineCholesterol, beeswax, stearyl alcohol and petroleum jelly
90 g 3-Methoxy-4-hydroxy-benzyliden-lävulinsäure ^O g 3-(p-Methylbenzyliden)-D,L-campher90 g of 3-methoxy-4-hydroxy-benzylidene-levulinic acid ^ O g 3- (p-methylbenzylidene) -D, L-camphor
bei 65 C zusammengeschmolzen. Jn diese warme Mischung wird ein auf die gleiche Temperatur erwärmtes Gemisch vonmelted together at 65 C. Jn this warm mixture becomes a mixture of heated to the same temperature
g Wasser
13g Borax
2 g p-Oxybenzoesäuremethylesterg of water
13g borax
2 g of methyl p-oxybenzoate
unter starkem Rühren eingearbeitet, und die erhaltene Creme wird bis zum Erreichen der Raumtemperatur weiter gerührt·incorporated with vigorous stirring, and the cream obtained is continued until it reaches room temperature touched·
7· Zur Herstellung einer Sonnenschutzemulsion wird in ein auf ca* 8O0C erwärmtes Gemisch von7 · For the preparation of a sun protection emulsion is in an on ca * 8O 0 C heated mixture of
20 g Glycerinmonostearat
- 70 g Stearinsäure
30 g Ölsäure
20 g Cetylalkohol20 g glycerol monostearate
- 70 g of stearic acid
30 g oleic acid
20 g of cetyl alcohol
80 g 3,U-Dimethoxy-benzyliden-lävulinsäure kO g p-Dimethylaminobenzoesäure-2-äthylhexylester80 g of 3, U-dimethoxy-benzylidene-levulinic acid kO g of p-dimethylaminobenzoic acid-2-ethylhexyl ester
- 12 -- 12 -
·0ββ82/0117· 0ββ82 / 0117
Henkel KGaA Patente und Literatur - 12 - D 5612Henkel KGaA Patents and Literature - 12 - D 5612
unter heftigem Rühren eine Mischung von 800 g Wasser, 10 ε Glycerin und 9 £ Triäthanolamin gegeben, Anschliessend wird die erhaltene Lotion kalt gerührt.a mixture of 800 g of water with vigorous stirring, 10 ε glycerine and 9 ε triethanolamine given, then the lotion obtained is stirred while cold.
Vorstehende Emulsion läßt sich auch unter MitVerwendung einer. Treibgases im Verhältnis 80 Teile Lotion : 20 Teilen Treibgas in Aerosolform verpacken..The above emulsion can also be used one. Pack propellant gas in the ratio 80 parts lotion: 20 parts propellant gas in aerosol form.
Anstelle der in den vorgenannten Rezepturen eingesetzten Brenztraubensäure- bzw, Lävulinsäurelcondensationsprodukte können auch die anderen vorstehend aufgeführten Brenztraubensäure- bzw, Lävulinsäurekondensationsprodukte verwendet werden, und an die Stelle der in den Rezepturen genannten UV-B-FiItersubstanzen können auch die anderen UV-B-Filtersubstanzen treten.Instead of the pyruvic acid or levulinic acid condensation products used in the aforementioned recipes The other pyruvic acid or levulinic acid condensation products listed above can also be used and the other UV-B filter substances can also be used in place of the UV-B filter substances mentioned in the recipes step.
•09882/0117• 09882/0117
Claims (3)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772728242 DE2728242A1 (en) | 1977-06-23 | 1977-06-23 | COSMETIC LIGHT PROTECTION AGENTS FOR THE UV-A AREA |
| NL7806036A NL7806036A (en) | 1977-06-23 | 1978-06-02 | COSMETIC, LIGHT PROTECTED PREPARATIONS FOR THE UV-A AREA. |
| IT24726/78A IT1097259B (en) | 1977-06-23 | 1978-06-20 | ANTI-SOLAR COSMETIC PRODUCT FOR THE UV-A FIELD |
| AT455078A AT355219B (en) | 1977-06-23 | 1978-06-22 | COSMETIC LIGHT PROTECTION AGENTS WITH A CONTENT OF FILTER SUBSTANCES FOR THE UV-A AREA AND, IF NECESSARY, ADDITIONAL UV-B FILTER SUBSTANCES |
| FR7818889A FR2395024A1 (en) | 1977-06-23 | 1978-06-23 | COSMETIC PRODUCTS FOR PROTECTION AGAINST LIGHT AND MORE SPECIFICALLY THE LIGHT OF THE REGION HAS ULTRAVIOLET SPECTRUM |
| CH689078A CH634987A5 (en) | 1977-06-23 | 1978-06-23 | Cosmetic light-stabilising agent for the UV-A region |
| BE188797A BE868398A (en) | 1977-06-23 | 1978-06-23 | COSMETIC PRODUCTS INTENDED TO PROTECT AGAINST LIGHT, IN PARTICULAR THE LIGHT OF THE REGION WITH THE ULTRAVIOLET SPECTRUM |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772728242 DE2728242A1 (en) | 1977-06-23 | 1977-06-23 | COSMETIC LIGHT PROTECTION AGENTS FOR THE UV-A AREA |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2728242A1 true DE2728242A1 (en) | 1979-01-11 |
Family
ID=6012159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772728242 Withdrawn DE2728242A1 (en) | 1977-06-23 | 1977-06-23 | COSMETIC LIGHT PROTECTION AGENTS FOR THE UV-A AREA |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT355219B (en) |
| BE (1) | BE868398A (en) |
| CH (1) | CH634987A5 (en) |
| DE (1) | DE2728242A1 (en) |
| FR (1) | FR2395024A1 (en) |
| IT (1) | IT1097259B (en) |
| NL (1) | NL7806036A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3938468A1 (en) * | 1989-11-18 | 1991-05-23 | Basf Ag | 1,1-DIALKOXY-2-OXO-6-ARYL-3,5-ALKADIENE |
| US5320833A (en) * | 1990-11-17 | 1994-06-14 | Basf Aktiengesellschaft | Arylpolyenecarboxylic acids and their derivatives as sunscreen agents in cosmetic preparations |
| DE4320871A1 (en) * | 1993-06-24 | 1995-01-05 | Beiersdorf Ag | Cosmetic and dermatological preparations containing delta amino levulinic acid |
| EP2104659A1 (en) * | 2007-01-08 | 2009-09-30 | AndroScience Corporation | Compounds with (substituted phenyl)-propenal moiety, their derivatives, biological activity, and uses thereof |
| WO2011014025A2 (en) * | 2009-07-30 | 2011-02-03 | 서울대학교 산학협력단 | Derivative of hydroxy-cinnamic acid in which a peptide has been bonded, production method for same, and cosmetic composition comprising same |
| US8710272B2 (en) | 2007-01-08 | 2014-04-29 | Androscience Corporation | Compounds with (1 E, 6E)-1,7-bis-(3,4-dimethoxyphenyl)-4,4-disubstituted-hepta-1,6-diene-3,5-dione structural scaffold, their biological activity, and uses thereof |
| US9000222B2 (en) | 2007-01-08 | 2015-04-07 | Androscience Corporation | Compounds with (1E, 6E)-1,7-bis-(3,4-dimethoxyphenyl)-4,4-disubstituted-hepta-1,6-diene-3,5-dione structural scaffold, their biological activity, and uses thereof |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4514383A (en) * | 1982-05-05 | 1985-04-30 | Johnson & Johnson Baby Products Company | Sunscreen compositions containing vinylogous amides |
| ITMI20010685A1 (en) * | 2001-03-30 | 2002-09-30 | Biochimici Psn S P A | DELTA-AMINOLEVULINIC ACID FOR MEDICAL AND COSMETIC USE |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2276204A (en) * | 1940-01-02 | 1942-03-10 | Kilgore Dev Corp | Chemical light filter |
| DE1045603B (en) * | 1957-06-06 | 1958-12-04 | Merck Ag E | Light stabilizers |
| FR1251590A (en) * | 1959-03-12 | 1961-01-20 | Agfa Ag | UV-absorbing light shielding agents |
| DE1134182B (en) * | 1960-03-07 | 1962-08-02 | Revlon | Browning protective agent against sunburn |
| FR2237912A1 (en) * | 1973-06-26 | 1975-02-14 | Oreal | Anti-sunburn polymers having aromatic chromophores - which absorb harmful UV frequencies, are used in cosmetic prepns. |
-
1977
- 1977-06-23 DE DE19772728242 patent/DE2728242A1/en not_active Withdrawn
-
1978
- 1978-06-02 NL NL7806036A patent/NL7806036A/en not_active Application Discontinuation
- 1978-06-20 IT IT24726/78A patent/IT1097259B/en active
- 1978-06-22 AT AT455078A patent/AT355219B/en not_active IP Right Cessation
- 1978-06-23 CH CH689078A patent/CH634987A5/en not_active IP Right Cessation
- 1978-06-23 FR FR7818889A patent/FR2395024A1/en not_active Withdrawn
- 1978-06-23 BE BE188797A patent/BE868398A/en not_active IP Right Cessation
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3938468A1 (en) * | 1989-11-18 | 1991-05-23 | Basf Ag | 1,1-DIALKOXY-2-OXO-6-ARYL-3,5-ALKADIENE |
| EP0429902A1 (en) * | 1989-11-18 | 1991-06-05 | BASF Aktiengesellschaft | 1,1-Dialkoxy-2-oxo-6-aryl-3,5-alkadienes |
| US5177222A (en) * | 1989-11-18 | 1993-01-05 | Basf Aktiengesellschaft | 1,1-dialkoxy-2-oxo-6-aryl-3,5-alkadienes |
| US5320833A (en) * | 1990-11-17 | 1994-06-14 | Basf Aktiengesellschaft | Arylpolyenecarboxylic acids and their derivatives as sunscreen agents in cosmetic preparations |
| DE4320871A1 (en) * | 1993-06-24 | 1995-01-05 | Beiersdorf Ag | Cosmetic and dermatological preparations containing delta amino levulinic acid |
| US5520905A (en) * | 1993-06-24 | 1996-05-28 | Beiersdorf Aktiengesellschaft | Cosmetic or dermatological preparation comprising delta-aminolevulinic acid content as an active ingredient |
| AU2008205312B2 (en) * | 2007-01-08 | 2013-11-21 | Annji Pharmaceutical Co., Ltd. | Compounds with (substituted phenyl)-propenal moiety, their derivatives, biological activity, and uses thereof |
| EP2104659A4 (en) * | 2007-01-08 | 2011-09-07 | Androscience Corp | Compounds with (substituted phenyl)-propenal moiety, their derivatives, biological activity, and uses thereof |
| US8202905B2 (en) | 2007-01-08 | 2012-06-19 | Androscience Corporation | Compounds with (substituted phenyl)-propenal moiety, their derivatives, biological activity, and use thereof |
| US8236852B2 (en) | 2007-01-08 | 2012-08-07 | Androscience Corporation | Compounds with (substituted phenyl)-propenal moiety, their derivatives, biological activity, and use thereof |
| EP2104659A1 (en) * | 2007-01-08 | 2009-09-30 | AndroScience Corporation | Compounds with (substituted phenyl)-propenal moiety, their derivatives, biological activity, and uses thereof |
| CN101711231B (en) * | 2007-01-08 | 2014-03-12 | 安德鲁科技有限公司 | Compounds with (substituted phenyl)-propenal moiety, their derivatives, biological activity, and uses thereof |
| US8710272B2 (en) | 2007-01-08 | 2014-04-29 | Androscience Corporation | Compounds with (1 E, 6E)-1,7-bis-(3,4-dimethoxyphenyl)-4,4-disubstituted-hepta-1,6-diene-3,5-dione structural scaffold, their biological activity, and uses thereof |
| US9000222B2 (en) | 2007-01-08 | 2015-04-07 | Androscience Corporation | Compounds with (1E, 6E)-1,7-bis-(3,4-dimethoxyphenyl)-4,4-disubstituted-hepta-1,6-diene-3,5-dione structural scaffold, their biological activity, and uses thereof |
| US9562025B2 (en) | 2007-01-08 | 2017-02-07 | Allianz Pharmascience Ltd. | Compounds with (1E, 6E)-1,7-Bis-(3,4-dimethoxyphenyl)-4-4-distributed-hepta-1,6-diene-3,5-dione structural scaffold, their biological activity, and uses thereof |
| WO2011014025A2 (en) * | 2009-07-30 | 2011-02-03 | 서울대학교 산학협력단 | Derivative of hydroxy-cinnamic acid in which a peptide has been bonded, production method for same, and cosmetic composition comprising same |
| WO2011014025A3 (en) * | 2009-07-30 | 2011-06-30 | 서울대학교 산학협력단 | Derivative of hydroxy-cinnamic acid in which a peptide has been bonded, production method for same, and cosmetic composition comprising same |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2395024A1 (en) | 1979-01-19 |
| NL7806036A (en) | 1978-12-28 |
| ATA455078A (en) | 1979-07-15 |
| IT1097259B (en) | 1985-08-31 |
| BE868398A (en) | 1978-12-27 |
| AT355219B (en) | 1980-02-25 |
| CH634987A5 (en) | 1983-03-15 |
| IT7824726A0 (en) | 1978-06-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |