EP1677752A1 - Skin and/or hair treatment agent containing tetrasubstituted cyclohexene compounds - Google Patents
Skin and/or hair treatment agent containing tetrasubstituted cyclohexene compoundsInfo
- Publication number
- EP1677752A1 EP1677752A1 EP04740896A EP04740896A EP1677752A1 EP 1677752 A1 EP1677752 A1 EP 1677752A1 EP 04740896 A EP04740896 A EP 04740896A EP 04740896 A EP04740896 A EP 04740896A EP 1677752 A1 EP1677752 A1 EP 1677752A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- skin
- hair
- acid
- agent according
- methyl
- 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- Withdrawn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
- 210000004209 hair Anatomy 0.000 title claims abstract description 88
- 125000000596 cyclohexenyl group Chemical class C1(=CCCCC1)* 0.000 title claims abstract description 16
- 238000011282 treatment Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 70
- 239000002537 cosmetic Substances 0.000 claims abstract description 51
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 39
- 230000008099 melanin synthesis Effects 0.000 claims abstract description 16
- 230000037308 hair color Effects 0.000 claims abstract description 13
- -1 hydroxypropyl Chemical group 0.000 claims description 80
- 150000001875 compounds Chemical group 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 42
- 239000000126 substance Substances 0.000 claims description 35
- 238000009472 formulation Methods 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000003963 antioxidant agent Substances 0.000 claims description 13
- 235000006708 antioxidants Nutrition 0.000 claims description 13
- 239000000839 emulsion Substances 0.000 claims description 13
- 239000003921 oil Substances 0.000 claims description 13
- 239000000975 dye Substances 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 150000003254 radicals Chemical class 0.000 claims description 12
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 10
- 239000000284 extract Substances 0.000 claims description 10
- 239000013543 active substance Substances 0.000 claims description 9
- 239000000049 pigment Substances 0.000 claims description 9
- 230000000699 topical effect Effects 0.000 claims description 9
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 claims description 8
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 8
- 229920000858 Cyclodextrin Polymers 0.000 claims description 8
- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 claims description 8
- 230000019612 pigmentation Effects 0.000 claims description 8
- 229920006395 saturated elastomer Chemical group 0.000 claims description 8
- 239000001993 wax Substances 0.000 claims description 8
- 239000004909 Moisturizer Substances 0.000 claims description 7
- 150000001298 alcohols Chemical class 0.000 claims description 7
- 239000006071 cream Substances 0.000 claims description 7
- 230000000254 damaging effect Effects 0.000 claims description 7
- 235000011187 glycerol Nutrition 0.000 claims description 7
- 229960005150 glycerol Drugs 0.000 claims description 7
- 230000001333 moisturizer Effects 0.000 claims description 7
- 229920000642 polymer Polymers 0.000 claims description 7
- 239000004753 textile Substances 0.000 claims description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 238000004140 cleaning Methods 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 239000000499 gel Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- BJRNKVDFDLYUGJ-RMPHRYRLSA-N hydroquinone O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-RMPHRYRLSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 239000011159 matrix material Substances 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 230000009759 skin aging Effects 0.000 claims description 6
- 239000007921 spray Substances 0.000 claims description 6
- 230000000475 sunscreen effect Effects 0.000 claims description 6
- 239000000516 sunscreening agent Substances 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 229940061720 alpha hydroxy acid Drugs 0.000 claims description 5
- 150000001280 alpha hydroxy acids Chemical class 0.000 claims description 5
- 238000004040 coloring Methods 0.000 claims description 5
- 210000002808 connective tissue Anatomy 0.000 claims description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
- 235000019136 lipoic acid Nutrition 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 230000004060 metabolic process Effects 0.000 claims description 5
- 230000003020 moisturizing effect Effects 0.000 claims description 5
- 230000036542 oxidative stress Effects 0.000 claims description 5
- 229920001282 polysaccharide Polymers 0.000 claims description 5
- 239000005017 polysaccharide Substances 0.000 claims description 5
- 239000002453 shampoo Substances 0.000 claims description 5
- 229960002663 thioctic acid Drugs 0.000 claims description 5
- 101100439665 Arabidopsis thaliana SWI2 gene Proteins 0.000 claims description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 4
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims description 4
- 244000303040 Glycyrrhiza glabra Species 0.000 claims description 4
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 claims description 4
- PESQCPHRXOFIPX-RYUDHWBXSA-N Met-Tyr Chemical compound CSCC[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 PESQCPHRXOFIPX-RYUDHWBXSA-N 0.000 claims description 4
- PESQCPHRXOFIPX-UHFFFAOYSA-N N-L-methionyl-L-tyrosine Natural products CSCCC(N)C(=O)NC(C(O)=O)CC1=CC=C(O)C=C1 PESQCPHRXOFIPX-UHFFFAOYSA-N 0.000 claims description 4
- 230000032683 aging Effects 0.000 claims description 4
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims description 4
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 4
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 4
- 235000020958 biotin Nutrition 0.000 claims description 4
- 239000011616 biotin Substances 0.000 claims description 4
- 229960002685 biotin Drugs 0.000 claims description 4
- 229960003624 creatine Drugs 0.000 claims description 4
- 239000006046 creatine Substances 0.000 claims description 4
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 238000005538 encapsulation Methods 0.000 claims description 4
- 235000020688 green tea extract Nutrition 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 229910052500 inorganic mineral Chemical class 0.000 claims description 4
- 239000011707 mineral Chemical class 0.000 claims description 4
- 239000002304 perfume Substances 0.000 claims description 4
- 239000011505 plaster Substances 0.000 claims description 4
- 102000004169 proteins and genes Human genes 0.000 claims description 4
- 108090000623 proteins and genes Proteins 0.000 claims description 4
- NHZMQXZHNVQTQA-UHFFFAOYSA-N pyridoxamine Chemical compound CC1=NC=C(CO)C(CN)=C1O NHZMQXZHNVQTQA-UHFFFAOYSA-N 0.000 claims description 4
- 108010005094 Advanced Glycation End Products Proteins 0.000 claims description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 3
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 claims description 3
- 102000008186 Collagen Human genes 0.000 claims description 3
- 108010035532 Collagen Proteins 0.000 claims description 3
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 claims description 3
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003412 L-alanyl group Chemical group [H]N([H])[C@@](C([H])([H])[H])(C(=O)[*])[H] 0.000 claims description 3
- 229930003268 Vitamin C Natural products 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000539 amino acid group Chemical group 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 claims description 3
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- 229930013032 isoflavonoid Natural products 0.000 claims description 3
- 150000003817 isoflavonoid derivatives Chemical class 0.000 claims description 3
- 235000012891 isoflavonoids Nutrition 0.000 claims description 3
- 229930187586 licochalcone Natural products 0.000 claims description 3
- 239000006210 lotion Substances 0.000 claims description 3
- 239000004530 micro-emulsion Substances 0.000 claims description 3
- 229920005862 polyol Polymers 0.000 claims description 3
- 150000003077 polyols Chemical class 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
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- 230000001256 tonic effect Effects 0.000 claims description 3
- 229940088594 vitamin Drugs 0.000 claims description 3
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- WCGUUGGRBIKTOS-GPOJBZKASA-N (3beta)-3-hydroxyurs-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C WCGUUGGRBIKTOS-GPOJBZKASA-N 0.000 claims description 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 2
- 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 claims description 2
- 125000000981 3-amino-3-oxopropyl group Chemical group [H]C([*])([H])C([H])([H])C(=O)N([H])[H] 0.000 claims description 2
- 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 claims description 2
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims description 2
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- YTBSYETUWUMLBZ-IUYQGCFVSA-N D-erythrose Chemical compound OC[C@@H](O)[C@@H](O)C=O YTBSYETUWUMLBZ-IUYQGCFVSA-N 0.000 claims description 2
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- 239000002244 precipitate Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 150000003142 primary aromatic amines Chemical class 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- PZQSQRCNMZGWFT-QXMHVHEDSA-N propan-2-yl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC(C)C PZQSQRCNMZGWFT-QXMHVHEDSA-N 0.000 description 1
- ZPWFUIUNWDIYCJ-UHFFFAOYSA-N propan-2-yl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)C ZPWFUIUNWDIYCJ-UHFFFAOYSA-N 0.000 description 1
- 229960002662 propylthiouracil Drugs 0.000 description 1
- 230000002797 proteolythic effect Effects 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical class NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 1
- 229940079889 pyrrolidonecarboxylic acid Drugs 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
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- 230000002829 reductive effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003726 retinal derivatives Chemical class 0.000 description 1
- 229940108325 retinyl palmitate Drugs 0.000 description 1
- 235000019172 retinyl palmitate Nutrition 0.000 description 1
- 239000011769 retinyl palmitate Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 description 1
- 229960004555 rutoside Drugs 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
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- 229960002718 selenomethionine Drugs 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
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- 229910052710 silicon Inorganic materials 0.000 description 1
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- 201000000849 skin cancer Diseases 0.000 description 1
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
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- 235000019983 sodium metaphosphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
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- 241000894007 species Species 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
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- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- ARCJQKUWGAZPFX-UHFFFAOYSA-N stilbene oxide Chemical compound O1C(C=2C=CC=CC=2)C1C1=CC=CC=C1 ARCJQKUWGAZPFX-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 210000000434 stratum corneum Anatomy 0.000 description 1
- 210000000437 stratum spinosum Anatomy 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
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- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 229940042585 tocopherol acetate Drugs 0.000 description 1
- 125000002640 tocopherol group Chemical class 0.000 description 1
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- 231100000331 toxic Toxicity 0.000 description 1
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- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
- ZCIHMQAPACOQHT-ZGMPDRQDSA-N trans-isorenieratene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/c1c(C)ccc(C)c1C)C=CC=C(/C)C=Cc2c(C)ccc(C)c2C ZCIHMQAPACOQHT-ZGMPDRQDSA-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
- LOIYMIARKYCTBW-UHFFFAOYSA-N trans-urocanic acid Natural products OC(=O)C=CC1=CNC=N1 LOIYMIARKYCTBW-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 108010031667 trichohyalin Proteins 0.000 description 1
- 229940040064 ubiquinol Drugs 0.000 description 1
- QNTNKSLOFHEFPK-UPTCCGCDSA-N ubiquinol-10 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC QNTNKSLOFHEFPK-UPTCCGCDSA-N 0.000 description 1
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- 239000011709 vitamin E Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/04—Preparations for care of the skin for chemically tanning the skin
-
- 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
- A61K8/67—Vitamins
- A61K8/671—Vitamin A; Derivatives thereof, e.g. ester of vitamin A acid, ester of retinol, retinol, retinal
-
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/70—Biological properties of the composition as a whole
Definitions
- the present invention relates to agents for use on the skin and / or hair, in particular for increasing skin tanning and melanin synthesis in the skin or hair.
- the invention encompasses cosmetic or dermatological preparations containing 4-times substituted cyclohexene compounds.
- the use of the preparations leads to the induction and intensification of the tanning mechanisms of the skin, to the intensification of the hair color and thus also to an increase in skin or hair protection.
- UVG range rays with a wavelength shorter than 290 nm
- UVB range rays in the range between 290 nm and 320 nm, the so-called UVB range, cause erythema , a simple sunburn or even more or less severe burns on the skin.
- UVA range It is also important to have filter substances available for the range between about 320 nm and about 400 nm, the so-called UVA range, since their rays can also cause damage. It has been shown that U VA radiation damages the elastic and collagen fibers of the connective tissue, which causes the skin to age prematurely, and that it can be seen as the cause of numerous phototoxic and photoallergic reactions is. The damaging influence of UVB radiation can be intensified by UV-A radiation.
- UVA radiation can also cause skin damage. by u. a. the skin's own keratin or elastin is damaged. As a result, elasticity and water
- UV radiation can also lead to photochemical reactions, in which case the photochemical reaction products interfere with the skin's metabolism.
- Such photochemical reaction products are predominantly radical compounds, e.g. Hydroxyl radicals.
- Undefined radical photo products which are created in the skin itself, can also display uncontrolled subsequent reactions due to their high reactivity.
- Singlet oxygen a non-radically excited state of the oxygen molecule can also occur under UV radiation, as can short-lived epoxies and many others.
- Singlet oxygen for example, is characterized by increased reactivity compared to the triplet oxygen that is normally present (radical ground state). However, there are also excited, reactive (radical) triplet states of the. Oxygen molecule.
- Such processes are very significantly involved in light-related skin aging (including wrinkling) due to oxidative damage to various skin structures.
- UV radiation also belongs to ionizing radiation. There is therefore a risk that ionic species also develop when exposed to UV, which in turn can then oxidatively intervene in the biochemical processes.
- the pigmentation of human skin is essentially caused by the presence of melanin.
- Melanin and its breakdown products (melanoids), carotene, the degree of blood circulation and the nature and thickness of the stratum comeum and other skin layers leave skin tones of practically white (with reduced filling or in the absence of blood vessels) or yellowish over light brown-reddish, bluish to brown different shades and finally appear almost black.
- the individual skin regions show different depths of color due to different amounts of melanin.
- melanin protects the skin from penetrating UV radiation.
- the number of melanin granules produced in the melanocytes determines whether the skin is light or dark.
- melanin is also in the stratum spinosum and even
- Hnhd-01938 (203-058-1) in the stratum corneum. It weakens the UV radiation by up to approx. 90% before it reaches the corium.
- melanocytes contain melanosomes, in which the melanin is formed. When stimulated by UV radiation, among other things, melanin is increasingly formed. This is ultimately transported into the horny layer (corneocytes) via the living layers of the epidermis (keratinocytes) and causes the more or less pronounced brown to brown-black skin color.
- Melanin is formed as the final stage of an oxidative process in which tyrosine, with the help of the enzyme tyrosinase, is converted into brown to brown-black eumelanins (DHICA and DHI melanin) or with the participation of sulfur-containing compounds to reddish pheomelanin with the help of the enzyme tyrosinase.
- DHICA and DHI melanin are produced via the common intermediate stages dopaquinone and d ⁇ pachrom.
- the latter is implemented, partly with the participation of further enzymes, either in indole-5,6-quinone carboxylic acid or in indole-5,6-quinone, from which the two eumelanins mentioned arise.
- the formation of phaeomelanin occurs among other things via the intermediates dopaquinone and cysteinyldopa.
- melanin In addition to various functions of the skin's own melanin, such as "detoxification'V connection of toxic substances / pharmaceuticals etc., the function of melanin as a natural UV filter to protect against damaging UV rays and the antioxidant function of melanin as protection against reactive oxygen species (oxidative Stress), which can occur due to solar radiation, among other things, is very important for the skin, also with regard to homeostasis, avoidance of skin aging, avoidance of sunburn, etc. This should not only result in a cosmetic benefit in the sense of increased tanning due to the increased Melanin synthesis in the skin after topical application of compounds which increase the melanogenesis result in additional protection through the various protective functions of melanin.
- oxidative Stress reactive oxygen species
- the object of the present invention is therefore to provide an agent, in particular a cosmetic or dermatological preparation, which enhances the natural tanning of the skin by means of increased melanin synthesis and at the same time leads to an increased protection of the skin.
- Skin type I never tans, always gets a sunburn.
- Skin type II hardly tans, easily gets a sunburn.
- Skin type III tans well on average.
- Skin type IV tans lightly and persistently, almost never gets sunburned.
- Skin type V dark, often almost black skin, never gets sunburned.
- the natural shielding of harmful UV radiation is a tangible advantage of natural skin tanning.
- a "healthy" skin color has also been a sign of sporting activity in particular and is therefore considered desirable by a wide range of consumers.
- Representatives of skin types I and II who want to enjoy such a skin tint are therefore dependent on self-tanning preparations anyway
- representatives of skin type III who are not too exposed to the risks of sunbathing and still want to look tanned are grateful target groups for self-tanning preparations.
- make-up or make-up preparations The easiest way to give your skin a brown hue is to apply appropriately colored make-up or make-up preparations. However, only those parts of the body that are covered by the colored preparations are of course stained. With the help of washable make-up preparations, a light skin tint can be achieved (e.g. extracts from fresh green walnut shells, henna).
- a disadvantage of the make-up is therefore the time-consuming procedure of applying. Another disadvantage is that they rub off heavily on textiles such as shirt collars or blouses.
- the different dyes can have different alfefgenen potency and even irritate the skin.
- the object of the present invention is therefore also to provide preparations which do not have the disadvantages of make-up tanning preparations.
- carotene By taking carotene supplements regularly, carotene is stored in the subcutaneous fatty tissue, the skin gradually turns orange to yellow-brown.
- Hnhd-01938 (203-058-1)
- the staining can also be done by chemical modification of the skin's skin layer with so-called self-tanning preparations.
- the most important active ingredient is dihydroxyacetone (DHA).
- DHA dihydroxyacetone
- the skin tanning achieved in this way cannot be washed off and is only removed with the normal desquamation of the skin (after approx. 10-15 days).
- Hydroxyacetone can be called etotriose and reacts as a reducing sugar with the amino acids of the skin or the free amino and i mino groups of keratin via a series of intermediates in the sense of a Maillard reaction to brown-colored substances, so-called melanoids, which are sometimes also called melanoidins.
- a particular disadvantage of tanning with dihydroxyacetone is that the skin tanned with it, in contrast to "sun-tanned" skin, is not protected against sunburn.
- dihydroxyacetone releases formaldehyde, in particular under the influence of ultraviolet radiation, even if mostly in small amounts. It was therefore an urgent need to have ways in which the decomposition of dihydroxyacetone can be effectively countered.
- An object of the present invention is to find alternatives to DHA as a self-tanning agent which do not have any disadvantageous properties, as are known from DHA.
- US 5093360 describes cosmetic or pharmaceutical preparations which contain retinal (vitamin A aldehyde) and / or their derivatives. Retinal or its derivatives are used in combination with active agents or as additives in various preparations to remedy dermatological errors.
- Retinal or its derivatives are used in combination with active agents or as additives in various preparations to remedy dermatological errors.
- tanning preparations which contain retinal or their derivatives in addition to the tanning agents.
- retinal or its derivatives alone have an effect on skin tanning.
- Hn d-01938 (203-058-1) Another type of artificial tanning, which is also completely independent of UV light, can be brought about by the hormones which are also released in the body as a result of (natural) UV radiation and ultimately stimulate the melanocytes to synthesize melanin.
- proopiomelanocortin such as aMSH
- synthetic variants such as N DP
- these hormones can generally bring about a tan, their use in cosmetics is forbidden since they are clearly pharmacologically active substances (hormones) * which should not be used widely without medical indication.
- Hair is the thread-like, almost universal (attached to the palms of the hands, soles of the feet, extensor sides of the toe and end of the fingers) skin appendages;
- 25 horny cells contains pigments) and the cuticle (cuticle pili; seedless epidermis layer) as well as layers of the epithelial and connective tissue hair sheath.
- the hair is divided into the hair shaft protruding from the skin and the sloping hair root reaching into the subcutis, the layers of which correspond approximately to those of the epidermis.
- the thickened lower end of the root, the hair bulb sits on a vascular connective tissue cone, the hair papilla, protruding into it (both as a hair floor).
- Melanin is responsible for the personal hair color.
- Melanin is formed in the melanocytes, cells that occur in the hair bulb in association with the keratinocytes of the hair market.
- Melanocytes contain - as characteristic cell organelles - melanosomes in which the melanin is formed. This is transferred via the long dendrites of the melanocytes into the keratinocytes of the precortical matrix and creates the more or less pronounced blonde to brown-black hair color.
- Melanin is formed as the final stage of an oxidative process, in which tyrosine with the help of the enzyme tyrosinase via several intermediate stages to the brown to brown-black eumelanins (DHICA and DHI melanin) or with the participation of.
- DHICA and DHI melanin brown to brown-black eumelanins
- phaeomelanin sulfur-containing compounds is converted to reddish phaeomelanin.
- DHICA and DHI melanin are produced via the common intermediate stages dopaquinone and dopach rom. The latter is converted, partly with the participation of further enzymes, either into indole-5,6-quinone carboxylic acid or into indole-5,6-quinone, from which the two called Eumelanine arise.
- the formation of phaeomelanin occurs among other things via the intermediates dopaquinone and cysteinyldopa. Cysteine is also necessary if the phaeomelanin is to be created for blonde and reddish hair.
- Eumelanin is the black-brown pigment. It is mainly about the depth of color of the hair. In brown and black hair it occurs in clearly recognizable granules.
- Phaeomelanin is the red pigment. It is responsible for light blonde, blonde and red hair. The structure of this melanin is much finer and smaller. The different hair colors result from the different proportions of the melanin types: • Blond hair contains little eumelanin and a lot of phaeomelanin. • Dark hair contains a lot of eumelanin and little phaeomelanin. • Red hair also has little eumelanin and a lot of phaeomelanin. • All shades of hair in between result from different mixing ratios of the two melanin types.
- Hnhd-01938 (203-058-I)
- the pigment formation process can only proceed if sufficient tyrosinase is available. This enzyme is produced less frequently with age. This gradually leads to gray hair. The reason: with little tyrosinase, less and less tyrosine is formed. The production of melanin also decreases. The missing melanin is replaced by the storage of air bubbles. The hair appears gray.
- This process is usually insidious. It begins at the temples and then extends to the entire hair on the head. Then it hits the beard and eyebrows. Finally, all of the body's hair is gray.
- gray hair is called canities.
- canities There are several ways of graying. Premature graying, from the age of 20, is also called Canities praecox.
- Symptoms of canities can have various causes. These include: Pernicious anemia (vitamin B deficiency anemia), severe endocrinological disorders, e.g. B. in thyroid diseases. acute, febrile diseases, drug side effects, cosmetics, metals.
- Pernicious anemia vitamin B deficiency anemia
- severe endocrinological disorders e.g. B. in thyroid diseases. acute, febrile diseases, drug side effects, cosmetics, metals.
- H ⁇ hd-01938 (203-058-1) preferably applied to the hair as a solution and remains there for a long time without being washed off.
- keratin fibers e.g. B. hair, wool or fur
- direct dyes or oxidation dyes which are formed by oxidative coupling of one or more developer components with one another or with one or more coupler components
- Coupler and developer components are also referred to as oxidation dye precursors.
- Primary aromatic amines with a further free or substituted hydroxy or amino group in the para or ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazone derivatives and 2,4,5,6-tetraaminopyrimidine and derivatives thereof are usually used as developer components used.
- M-Phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols are generally used as coupler components.
- Suitable coupler substances are, in particular, ⁇ -naphthol, 1, 5-, 2,7- and 1, 7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 2 , 4-diamine .
- ophenoxyethanol 1-phenyl-3-methyl-pyrazolon-5, 2,4-dichloro-3-aminophenol, 1, 3-bis (2,4-diaminophenoxy) propane, 2-chlororesorcinol, 4-chlororesorcinol, 2 -Chlor-6-methyl-3-aminophenol, 2-methylresorcinol and 5-methylresorcinol.
- Hnhd-01938 (203-058-1) European Commission, available in diskette form from the Federal Association of German Industry and Commerce for Medicinal Products, Health Care Products and Personal Care Products, Mannheim.
- oxidation dyes intensive dyeings can be achieved with good fastness properties, but the development of the color is generally done under the influence of oxidizing agents such. B. H 2 0 2 , which in some cases can result in damage to the fiber. Furthermore, some oxidation dye precursors or v certain mixtures of oxidation dye precursors can have a sensitizing effect sometimes in people with sensitive skin. Direct dyes are applied under gentler conditions, but their disadvantage is that the dyeings often have inadequate fastness properties.
- the object of the present invention is to improve the independent melanin production of the hair, but without coloring agents and in particular oxidizing agents such. B. H 2 O 2 to be instructed.
- the agents must have no or only a very low sensitization potential.
- the invention includes the use of such agents and the compounds according to the invention as agents for increasing the tan or the melanin synthesis in the skin or hair.
- cosmetic or dermatological preparations contain one or more compounds of the structure
- R1, R2 and / or R5 are selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxy and / or alkyl carboxylates with alkyl radicals selected from methyl, ethyl , Propyl or butyl, preferably is methyl;
- R6 and / or R7 are selected from the group consisting of methyl, hydrogen, ethyl, propyl, isopropyl, butyl, tert-butyl, hydroymethyl, hydroxyethyl, hydroxypropyl, hydroxy or alkyl carboxylate, the alkyl radical being selected from methyl, ethyl, propyl or Butyl, methyl is preferred;
- R4 is selected from carbonyl oxygen, amino acid residues Ala, Ser, Gly, Val, Leu, lle, Pro, Trp, Phe, Met Tyr, Thr, Cys, Asn, Asp, Glu, Lys, Arg, Gin, H, Orn, Sar , Hyl, Hyp, Hse or Hey, preferably Ala, Ser or Gly, - residues of the structure N- (CH 2 ) x -OH, N- (CHR9) x -CH2OH, N- (CH 2 ) x -OCOMe, where each
- R9 is selected from hydrogen and / or hydroxy
- R11 is selected from methyl, hydroxymethyl, hydrogen, prop-2-yl, isobutyl, but-2-yl, pyrrolidin-1, 2-diyl, 1 H-indol-3-yl-methyl, benzyl; 2- (methylthio) ethyl, 4-hydroxy-benzyl, 1-hydroxyethyl, mercaptomethyl, 2-amino-2-oxoethyl, carboxymethyl, carboxyethyl, 4-aminobutyl, 3 - ⁇ [amino (imino ) methyl] amino ⁇ propyl, 3-amino-3-oxopropyl, hydrogen and N-Me, 3-aminopropyl, ethyl, 1 H-imidazol-4-yl-methyl, butyl, propyl, 4 -Amino-3-hydroxy-butyl-, 4-hydroxy-pyrrolidin-1, 2-diyl-, hydroxy
- R12 is selected from mono- to polysaccharides, preferably uniform and / or mixed mono-, di- or trisaccharides, preferably glucose, glycerose, erythrose, threose, ribose, arabinose, lyxose, xylose, ailose, altrose, galactose, gose, idose , Mannose or talose.
- mono- to polysaccharides preferably uniform and / or mixed mono-, di- or trisaccharides, preferably glucose, glycerose, erythrose, threose, ribose, arabinose, lyxose, xylose, ailose, altrose, galactose, gose, idose , Mannose or talose.
- the compounds are 9-retinal of the structural formula
- the substances according to the invention are outstandingly suitable for bringing about increased tanning of the skin.
- Suitable are all compounds of the structures listed above which the person skilled in the art can select from the respective groups without being inventive.
- the person skilled in the art will, in particular, be used for cosmetic or dermatological purposes
- Hnhd-01938 (203-058-1) Choose preferably only those whose tolerability, toxicology and the like, are not critical.
- the skin's own melanin has various functions, such as "detoxification'V connection of toxic substances / pharmaceuticals.
- the function of melanin as a natural UV filter for protection against harmful UV rays and the antioxidant function of melanin as protection against reactive oxygen species (oxidative Stress), which can occur due to sun radiation is very important for the skin, also in relation to homeostasis, avoidance of skin aging, avoidance of sunburn, etc. This should not only result in a cosmetic benefit in the sense of increased tanning due to the increased Melanin synthesis in the skin after topical application of compounds which increase the melanogenesis according to the invention also provide additional protection through the various protective functions of melanin.
- the substances according to the invention are suitable for strengthening the physiological tanning of the skin by means of an increased melanin synthesis and thus also increasing the skin's own protection.
- a major advantage is that this physiological tanning is achieved without having to be exposed to natural solar radiation with its damaging influences on the skin or that this is only necessary to a comparatively small extent in order to achieve the desired skin tanning.
- uneven skin pigmentations (“uneven skin tone") are also compensated.
- the advantage the complexion appears more uniform, which is particularly desirable for aging skin (age spots), melasma and post-inflammatory hyperpigmentation.
- the invention therefore preferably relates to cosmetic or dermatological preparations containing compounds according to the invention, as defined above.
- the invention also relates to the use of the preparations thus produced.
- the compounds according to the invention comprise ring-shaped hydrocarbon compounds, the ring-shaped structure preferably being composed of 6 carbon atoms and being partially to completely unsaturated and additionally having several, in particular 4, hydrocarbon substituents.
- the compounds according to the invention are simply referred to as tetrasubstituted cyclohexene compounds.
- 3 substituents are short-chain, preferably consisting of a methyl group (R1, R2 and R5), a further, fourth, substituent (R3), which also consists of
- a branched and / or partially to completely unsaturated hydrocarbon compound can comprise 1 to 25 carbon atoms, but preferably at least 4 and at most 20 carbon atoms.
- the end of the “fourth substituent” opposite the annular structure preferably, but not necessarily, has a polar end.
- the 4-fold substituted compounds according to the invention could be crystallized out as suitable compounds for use on human skin and hair.
- Three basic building blocks, the cyclohexene ring, the structure and chain length of the radical R3 and its functional groupings or polarities are essential. All of these findings lead to the compounds according to the invention, which the person skilled in the art can select according to structure (I) and any remaining information.
- the 4-fold substituted cyclohexene compounds according to the invention are known per se, at least from a synthetic point of view, but are not mentioned in connection with their suitability as agents for use on the skin or hair.
- the person skilled in the art can select a compound from the group of compounds listed in claim 1 as required and even combine it with other compounds in order to achieve the effects which are advantageous according to the invention. It follows from this that the compound according to the invention has the following general structure:
- R1, R2 and R5 is preferably a methyl radical and R3 in the manner described above creates a C 1 -C 25 radical, preferably a C 4 -C 20 radical, d, which preferably forms a polar at the opposite end Group has.
- ⁇ / -3,7-dimethyl-9- (2,6,6-trimethylcyclohex-1-en-1-yl) nona-2,4,6,8-tretraen-1-ylidenes] is alanine preferred, characterized by the structure.
- Hnhd-01938 (203-058-1) wherein R4 represent amino acids bound via an imino functionality, in particular glycine and serine, and R1, R2, R5, R6 and R7 is a methyl radical.
- R4 represent amino acids bound via an imino functionality, in particular glycine and serine
- R1, R2, R5, R6 and R7 is a methyl radical.
- the following synthesis instructions are cited as examples: Rani, Aruna V., Tet Lett, 33, 10, 1992, 1379-1382 and Pshenichnikova, AB, Russ. J. Bioorg. Chem., 22, 11, 1996, 744-747 and Int J. Vitamin and Nutrition Research, 62, 4, 1992, 298-302 and EP 440078 A2. s.
- connection structure (I) From the connection structure (I), the following preferred connections (IUPAC names) with the specified structures result:
- R1, R2, R5, R6 and R7 as the methyl radical and R4 as the radical of the structure N-OH.
- R1, R2, R5, R6 and R7 as the methyl radical
- connection structure (I) also gives the following
- acetyl retinyliminoethanol The manufacturing instructions for acetyl retinyliminoethanol are as follows:
- the mixture is filtered and the solvent is removed on a rotary evaporator.
- compositions in particular cosmetic or dermatological preparations, lead to the induction of pigmentation of the skin.
- the compounds according to the invention in suitable preparations, lead to an intensification of the hair color, with which natural graying of the hair can also be avoided and even reversed.
- the activation of the skin's own tanning and the intensification of hair coloring can of course be done with and without the involvement of UV light.
- a melanogenesis assay was carried out after 3 days of incubation of primary normal human melanocytes with test substance versus control.
- Hnhd-01938 (203-058-1)
- the compounds according to the invention are distinguished, inter alia, by the fact that, after topical application, they induce the formation of the skin's own pigments in the skin, increase the melanin synthesis and in this way produce an increased tanning of the skin handle, and the resulting shade naturally corresponds to that of the natural healthy skin color.
- the browning obtained - which corresponds to the natural tanning - is lightfast and cannot be washed off.
- the preparations according to the invention also surprisingly intensify the tanning of already tanned skin and furthermore delay the bleaching of tanned skin. Another advantage of the present invention results from the protective benefits of natural melanin formed in the skin.
- melanin In addition to various other functions of the skin's own melanin (such as “detoxification” or binding of toxic substances and / or pharmaceuticals etc.), these functions of melanin are also very important for the skin, in particular with regard to homeostasis, the avoidance of Skin aging and the like:
- Melanin acts as a natural UV filter to protect against damaging UV rays and also as an antioxidant to protect against reactive oxygen species (oxidative stress), which can occur, among other things, from sun exposure.
- agents according to the invention e.g. Cosmetic or dermatological preparations induce the formation of skin and hair-specific pigments in the skin and hair, intensify the existing natural and / or artificial tanning of the skin, compensate for inconsistent pigmentation of the skin, intensify the natural hair coloring and leave the skin tanning as the hair coloring also last longer.
- the formulations according to the invention are extremely satisfactory preparations which are distinguished by a uniform coloring effect. It was not foreseeable for the person skilled in the art that the formulations according to the invention
- Hnhd-01938 (203-058-1) ⁇ give the skin and hair a natural look faster and better
- ⁇ better promote smoothing of the skin, ⁇ are characterized by better care effects
- ⁇ have better sensory properties, such as, for example, the spreadability on the skin and hair or the ability to be absorbed into the skin, and
- ⁇ would offer better / risk-free protection of the skin and hair (against UV radiation) than the preparations of the prior art.
- the formulations according to the invention surprisingly have no hormonal effects.
- the content of the compounds is between 0.0001 and 30% by weight, advantageously between 0.01 and 10% by weight, particularly advantageously between 0.02 and 2% by weight, in each case based on the total weight of the composition.
- the cosmetic and / or dermatological formulations according to the invention can be composed as usual and can be used in particular for the treatment and care of the skin and / or hair, as a make-up product in decorative cosmetics or as a sunscreen or so-called pre or after preparation.
- the formulations according to the invention can be used, for example, as skin protection cream, face cream, cleansing milk, sunscreen lotion, nutrient cream, day or night cream, etc.
- compositions are usually inconceivable without the customary auxiliaries and additives.
- auxiliaries and additives include, for example, consistency enhancers, fillers, perfumes, dyes, emulsifiers, additional active ingredients such as vitamins or proteins, light stabilizers, stabilizers, insect repellents, alcohol, water, salts, antimicrobial, proteolytic or keratolytically active substances, etc.
- Hnhd-01938 (203-058-1) It is also advantageous to present the compound or compounds according to the invention in encapsulated form, for example in collagen matrices and other customary encapsulation materials, such as, for example, cyclic oligosaccharides (in particular alpha, beta, HP-beta, random-Me-beta, gamma-cyclodextrin), where, according to the chemical properties known to the person skilled in the art, alpha-, beta- or gamma-cyclodextrins are used as encapsulation material.
- cyclic oligosaccharides in particular alpha, beta, HP-beta, random-Me-beta, gamma-cyclodextrin
- the compounds according to the invention may be advantageous to present the compounds according to the invention or their mixtures in the form of cellulose encapsulations, encapsulated in gelatin, wax matrices or liposomally.
- cyclodextrins it is assumed that the cyclodextrin skeletons act as the host molecule and the active ingredient according to the invention acts as the guest molecule.
- cyclodextrins are dissolved in water and the active ingredient according to the invention is added. The molecular adduct then precipitates as a solid and can be subjected to the usual cleaning and preparation steps.
- Medical topical compositions in the sense of the present invention generally contain one or more drugs in effective concentration.
- the compound (s) according to the invention is also advantageous to add the compound (s) according to the invention as an additive to preparations which already contain other active ingredients for other purposes.
- the formulations according to the invention are also particularly suitable for combinations with active ingredients which have a positive effect on the condition of the skin. It has been shown that active ingredients to positively influence the aging skin, which reduce the appearance of wrinkles or existing wrinkles. So especially in
- Hnhd-01938 (203-058-1) Combination with bioquinones, especially ubiquinone Q10, creatine, creatinine, camitin, biotin, isoflavone, cardiolipin, lipoic acid, anti freezing proteins, hop and hop malt extracts.
- Promotional agents for the restructuring of the connective tissue such as isoflavonoids and isoflavonoid-containing plant extracts such as, for example, soybean and clover extracts, can also be used very well in the formulations according to the invention.
- formulations are particularly suitable, active ingredients to support skin functions in dry skin, such as vitamin C, biotin, camitin, creatine, propionic acid, green tea extracts, eucalyptus oil, urea and mineral salts such as. B. NaCI, marine minerals and osmolytes such. B. taurine, inositol, betaine, quaternary ammonium compounds to use.
- active ingredients to support skin functions in dry skin such as vitamin C, biotin, camitin, creatine, propionic acid, green tea extracts, eucalyptus oil, urea and mineral salts such as. B. NaCI, marine minerals and osmolytes such. B. taurine, inositol, betaine, quaternary ammonium compounds to use.
- active ingredients to support skin functions in dry skin such as vitamin C, biotin, camitin, creatine, propionic acid, green tea extracts, eucalyptus oil, urea and mineral salts
- Active substances such as sericosides, various extracts of liquorice, licochalcones, in particular licochalocon A, silymarin, silyphos, dexpanthenol, inhibitors of prostaglandin metabolism, in particular cyclooxygenase and leukotriene metabolism, in particular 5-lipoxyenase, but also 5- Lipoxvase inhibitor protein, FLAP.
- the incorporation of pigmentation modulators also proved to be advantageous. Active substances are to be mentioned here which reduce the pigmentation of the skin and thus lead to a cosmetically desired lightening of the skin and / or reduce the appearance of age spots and / or lighten existing age spots.
- Examples include tyrosine sulfate, dioic acid (8-hexadecen-1, 16-dicarboxylic acid as well as lipoic acid and liponamide, various extracts of licorice. Kojic acid, HydroGhinon, arbutin, fruit acids, especially alpha-hydroxy acids (AHAs), bearberry (Uvae ursi ), Ursolic acid, ascorbic acid, green tea extracts, aminoguanidine, pyridoxamine.
- the formulations according to the invention proved to be excellent combination partners for other active ingredients which bring about enhanced or faster tanning of the skin (advanced glycation end products (AGE), lipofuscins, nucleic acid oligonucleotides, Purines and pyrimidines, NO-releasing substances), be it with or without the influence of UV light.
- AGE glycation end products
- lipofuscins lipofuscins
- nucleic acid oligonucleotides nucleic acid oligonucleotides
- Purines and pyrimidines Purines and pyrimidines
- NO-releasing substances advanced glycation end products
- Cosmetic and dermatological preparations in the form of a sunscreen are particularly preferred. These can advantageously also have at least one further UVA filter and / or at least one further UVB filter
- cosmetic and dermatological preparations according to the invention are able to prolong the natural tanning process.
- cosmetic and dermatological formulations according to the invention are able to serve for the treatment of hypopigmentation (vitiligo, uneven pigmentation in aging skin, etc.).
- the cosmetic and dermatological preparations can contain cosmetic auxiliaries as are usually used in such preparations, e.g. Preservatives, bactericides, perfumes, substances to prevent foaming, dyes, pigments that have a coloring effect, thickeners, moisturizing and / or moisturizing substances, fats, oils, waxes or other common components of a cosmetic or dermatological formulation such as alcohols, polyols, Polymers, foam stabilizers, electrolytes, organic solvents, silicone derivatives or moisturizers.
- cosmetic auxiliaries e.g. Preservatives, bactericides, perfumes, substances to prevent foaming, dyes, pigments that have a coloring effect, thickeners, moisturizing and / or moisturizing substances, fats, oils, waxes or other common components of a cosmetic or dermatological formulation such as alcohols, polyols, Polymers, foam stabilizers, electrolytes, organic solvents, silicone derivatives or moisturizers.
- Moisturizers are substances or mixtures of substances that give cosmetic or dermatological preparations the property that after application or distribution, the release of moisture from the skin layer on the skin surface (also
- moisturizers for the purposes of the present invention are, for example, glycerin, lactic acid, pyrrolidone carboxylic acid and urea. Furthermore, it is particularly advantageous to use polymeric moisturizers from the group of water-soluble and / or water-swellable and / or water-gelable polysaccharides. Particularly advantageous are, for example, hyaluronic acid and / or a fucose-rich polysaccharide, which is filed in the Chemical Abstracts under the registration number 178463-23-5 and z. B. under the name Fucogel®1000 from the company SOLABIA S.A. is available.
- Glycerin can be used as a moisturizer in the sense of the present application in the range of 0.05-30% by weight, particularly preferably 1-10%.
- antioxidants in the preparations according to the invention are generally preferred. According to the invention, all the antioxidants suitable or customary for cosmetic and / or dermatological applications can be used as favorable antioxidants.
- antioxidants are advantageously selected from the group consisting of amino acids (for example glycine, histidine, tyrosine, phenylalanine, tryptophan) and their derivatives (in particular N-acetyl-tyrosine, N-acetyl-phenylalanine), imidazoles (for example urocanic acid) and their Derivatives, peptides such as DL-camosin, D-camosin, L-camosin and their derivatives (e.g. anserine), carotenoids, carotenes (e.g.
- amino acids for example glycine, histidine, tyrosine, phenylalanine, tryptophan
- imidazoles for example urocanic acid
- peptides such as DL-camosin, D-camosin, L-camosin and their derivatives (e.g. anserine), carotenoids, carotenes (e.g.
- -carotene, ⁇ -carotene, lycopene and their derivatives, chlorogenic acid and its derivatives, lipoic acid and its derivatives (e.g. dihydroliponic acid), aurothioglucose, propylthiouracil and other thiols (e.g.
- thioredoxin glutathione, cysteine, cystine, cystarmine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, Palmitoyl, oleyl, linoleyl, cholesteryl and glyceryl esters) and their salts, dilaurylthlodipropionate, distearylthio dipropionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and sulfoximine compounds (e.g.
- ⁇ -hydroxy fatty acids palmitic acid, phytic acid, lactoferrin
- ⁇ -Hydroxy acids eg citric acid, lactic acid, malic acid
- humic acid eg citric acid, lactic acid, malic acid
- bile acid e.g. g citric acid, lactic acid, malic acid
- humic acid e.g citric acid, lactic acid, malic acid
- bile acid e extracts
- bilirubin biliverdin
- EDTA EGTA
- unsaturated fatty acids and their derivatives eg ⁇ -linolenic acid, linoleic acid, oleic acid
- folic acid e.g.
- ascorbyl palmitate Mg ascorbyl phosphate, ascorbyl acetate), tocopherols and derivatives (e.g. vitamin E acetate), vitamin A and derivatives (vitamin A palmitate) and coniferyl - benzoate of benzoin, rutinic acid and their 'derivatives, ⁇ -Glycosylrütin, ferulic acid, Furfurylidenglucitol, carnosine, butylhydroxytoluene, butylhydroxyanisole,
- the amount of the aforementioned antioxidants (one or more compounds) in the preparations is preferably 0.001 to 30% by weight, particularly preferably 0.05-20% by weight, in particular 1-10% by weight, based on the total weight of the Preparation.
- vitamin E and / or its derivatives turn on the antioxidant (s) d, it is advantageous to choose their respective concentrations from the range from 0.001 to 10% by weight, based on the total weight of the formulation. If vitamin A or vitamin A derivatives or carotenes or their derivatives represent the antioxidant or antioxidants, it is advantageous to use their respective concentrations in the range from 0.001-10% by weight, based on the total weight of the formulation, to choose.
- Cosmetic or dermatological formulations in the sense of the present invention can preferably contain, in addition to one or more oil phases, one or more water phases and, for example, in the form of W / O-, O / W-, W / O / W- or O ⁇ / V / O- Emulsions are present.
- Such emulsions can preferably also be a microemulsion, a Pickering emulsion or a sprayable emulsion.
- formulations according to the invention can also advantageously be in the form of oil-free preparations, such as gels, or as anhydrous preparations.
- formulations according to the invention can furthermore advantageously also contain dihydroxyacetone or nut extracts as well as other substances which are intended to maintain or produce the tan or to additionally reinforce them.
- the lipid phase of the emulsions according to the invention can advantageously be selected from the following group of substances: mineral oils, mineral waxes
- Oils such as triglycerides of capric or caprylic acid, but preferably castor oil; Fats, waxes and other natural and synthetic fat bodies, preferably esters of fatty acids with alcohols with a low C number, for example with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids with a low C number or with fatty acids; benzoates; Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and mixed forms thereof.
- the oil phase of the emulsions, oligogels or hydrodispersions or lipodispersions within the meaning of the present invention is advantageously selected from the group of esters from saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 3 to 30 C atoms and saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 3 to 30 C atoms, from the group of esters from aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols Chain length from 3 to 30 carbon atoms.
- ester oils can then advantageously be selected from.
- the oil phase can also advantageously be selected from the group of branched and unbranched hydrocarbons and waxes, silicone oils, dialkyl ethers, the group of saturated or unsaturated, branched or unbranched alcohols, and also fatty acid triglycerides, especially the triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 8 to 24, in particular 12 - 18 carbon atoms.
- the fatty acid triglycerides can for example advantageously be selected from the group of synthetic, semi-synthetic and natural oils, e.g. Olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, coconut oil, palm kernel oil and the like.
- Hnhd-01 ' 938 (203-058-I) be waxes, for example cetyl palmitate, to be used as the sole lipid component of the oil phase.
- the oil phase is advantageously selected from the group 2-ethylhexyl isostearate, octyldodecanol, isotridecyl isononanoate, isoeicosane, 2-ethylhexyl cocoate, C 12-15 alkyl benzoate, caprylic capric acid triglyceride, dicaprylyl ether.
- Mixtures of d 2 are particularly advantageous.
- hydrocarbons paraffin oil, squalane and squalene can be used advantageously for the purposes of the present invention.
- the oil phase can advantageously also have a content of cyclic or linear silicone oils or consist entirely of such oils, although it is preferred to use an additional content of other oil phase components in addition to the silicone oil or the silicone oils.
- Cyclomethicone (Oetamethyleyclotetrasiloxane) is advantageously used as the silicone oil to be used according to the invention.
- other silicone oils can also be used advantageously for the purposes of the present invention, for example hexamethylcyclotrisiloxane, polydimethylsiloxane, poly (methylphenylsiloxane).
- Mixtures of cyclomethicone and isotridecyl isononanoate, of cyclomethicone and 2-ethylhexyl isostearate are also particularly advantageous.
- the aqueous phase of the preparations according to the invention advantageously advantageously contains - alcohols, diols or polyols of low C number, and also their ethers, preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or - monobutyl ether, diethylene glycol monomethyl or rnonoethyl ether and analogous products, furthermore alcohols of low C number, for example Ethanol, isopropanol, 1,2-propanediol, glycerol and in particular one or more thickeners, which one or more can advantageously be selected from the group
- Hnhd-01938 (203-058-1) Silicon dioxide, aluminum silicates, polysaccharides or their derivatives, for example hyaluronic acid, xanthan gum, hydroxypropylmethyl cellulose, particularly advantageously from the group of polyacrylates, preferably a polyacrylate from the group of so-called carbopoles, for example carbopoles of types 980, ' 981, 1382, 2984, 5984, individually or in combination.
- UV filter substances can also be added to the preparation according to the invention.
- Particularly advantageous UV filter substances which are liquid at room temperature for the purposes of the present invention are homomenthyl salicylate (INCI: homosalate), 2-ethylhexyl-2-cyano-3,3-diphenylacrylate (INCI: octocrylene), 2-ethylhexyl-2-hydroxybenzoate (2- Ethyl hexyl salicylate, octyl salicylate, I NCI: octyl salicylate) and esters of cinnamic acid, preferably 4-methoxycinnamic acid (2-ethylhexyl) ester (2-ethylhexyl 4-methoxycinnamate, INCI: octyl methoxycinnamate) and 4-methoxycinnamate acid (l-methoxycinnamate) 4-methoxycinnamate, INCI: isoamyl
- Preferred inorganic pigments are metal oxides and / or other metal compounds which are sparingly soluble or insoluble in water, in particular oxides of titanium (Ti0 2 ), zinc (ZnO), iron (e.g. Fe 2 0 3 ), zirconium (ZrO 2 ), silicon ( SiO 2 ), manganese (e.g. MnO), aluminum (Al 2 O 3 ), cerium (e.g. Ce 2 0 3 ), mixed oxides of the corresponding metals as well as mixtures of such oxides and the sulfate of barium, (BaS0 4 ).
- the pigments can also advantageously be used in the form of commercially available oily or aqueous predispersions.
- the pigments can advantageously be surface-treated (“coated”), for example, a hydrophilic, amphiphilic or hydrophobic character should be formed or retained.
- This surface treatment can consist in that the pigments are prepared using a thin hydrophilic and In the sense of the present invention, the various surface coatings can also contain water.
- Inorganic surface coatings in the sense of the present invention can consist of aluminum oxide (Al 2 0 3 ), aluminum hydroxide Al (OH) 3 , or aluminum oxide hydrate (also: alumina, CAS no .: 1333-84-2), sodium hexametaphosphate (NaP0 3 ) 6 , sodium metaphosphate (NaP0 3 ) n , silicon dioxide (SiO 2 ) (also: silica, CAS no. : 7631-86- Hnhd-01938 (203-058-I) 9), or iron oxide (Fe 2 0 3 ).
- These inorganic surface coatings can occur alone, in combination and / or in combination with organic coating materials.
- Organic surface coatings in the sense of the present invention can consist of vegetable or animal aluminum stearate, vegetable or animal stearic acid, lauric acid, dimethylpolysiloxane (also: dimethicone), methylpolysiloxane (methicone), simethicone (a mixture of dimethylpolysiloxane with an average chain length of 200 to 350 dimethylsiloxane -Units and Siltcagel) or alginic acid.
- dimethylpolysiloxane also: dimethicone
- methicone methylpolysiloxane
- simethicone a mixture of dimethylpolysiloxane with an average chain length of 200 to 350 dimethylsiloxane -Units and Siltcagel
- alginic acid can consist of vegetable or animal aluminum stearate, vegetable or animal stearic acid, lauric acid, dimethylpolysiloxane (also: dimethicone), methylpoly
- Zinc oxide particles and predispersions of zinc oxide particles suitable according to the invention are available under the following trade names from the listed companies:
- Suitable titanium dioxide particles and predispersions of titanium dioxide particles are available under the following trade names from the companies listed:
- UV-A filter substances for the purposes of the present invention are dibenzoyl methane derivatives, in particular 4- (tert-butyl) -4'-methoxydibenzoyl methane (CAS No. 0 70356-09-1), which is sold by Givaudan under the brand name Parsol ® 1789 and sold by Merck under the trade name Eusolex® 9020.
- Advantageous further UV filter substances in the sense of the present invention are sulfonated, water-soluble UV filters, such as.
- Hnhd-01938 especially the phenylene-1,4-bis (2-benzimidazyl) -3,3'-5,5'-tetrasulfonic acid bis-sodium salt with the INCI name bisimidazylate (CAS No .: 180898-37-7 ), which is available, for example, from Haarmann & Reimer under the trade name Neo Heliopan AP; • Salts of 2-phenylbenzimidazole-5-sulfonic acid, such as its sodium, potassium or triethanolammonium salt and the sulfonic acid itself with the INCI name phenylbenzimidazole sulfonic acid (CAS No.
- Advantageous UV filter substances in the sense of the present invention are also so-called broadband filters, i.e. Filter substances that absorb both UV-A and UV-B radiation.
- Advantageous broadband filters or UV-B filter substances are, for example, triazine derivatives, such as. B.
- Hnhd-01938 (203-058-1) is available under the trade name Tinosorb® M from CIBA-Chemicals GmbH.
- Another invention is 2- (2H-benzotriazol-2-yl) -4-methyl-6- [2-methyl-3- [1, 3,3,3-tetramethyl-1 - [(trimethylsilyl) oxy] di- siloxanyl] propyl] phenol (CAS No .: 155633-54-8) with the INCI name Drometrizole Trisiioxane, which is available under the trade name Mexoryl® XL from Chimex.
- the other UV filter substances can be oil-soluble or water-soluble.
- Advantageous oil-soluble UV-B and / or broadband filter substances in the sense of the present invention are e.g. B .:
- 3-benzylidene camphor derivatives preferably 3- (4-methylbenzylidene) camphor, 3-benzylidene camphor;
- 4-aminobenzoic acid derivatives preferably 4- (dimethylamino) benzoic acid (2-ethylhexyl) ester, 4- (dimethylamino) benzoic acid amyl ester;
- benzophenone preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone
- Advantageous water-soluble filter substances are e.g. B .:
- Sulfonic acid derivatives of 3-benzylidene camphor such as. B. 4- (2-oxo-3-bornylidene methyl) benzenesulfonic acid, 2-methyl-5- (2-oxo-3-bornylidene methyl) sulfonic acid and salts thereof.
- a further light protection filter substance according to the invention to be used advantageously is ethylhexyl-2-cyano-3,3-diphenylacrylate, obtainable (octocrylene) from BASF under the name Uvinul ® N 539th
- Particularly advantageous preparations within the meaning of the present invention which are distinguished by a high or very high UV-A and / or UV-B protection, preferably contain further UV-A and in addition to the filter substance (s) according to the invention / or broadband filter, in particular dibenzoylmethane derivatives [for example the 4- (tert-butyl) -4'-methoxydibenzoylmethane], phenylene-1, 4-bis- (2-benzimidazyl) -3,3'-5,5'-tetrasulfonic acid and / or their salts, the 1,4-di (2-oxo-10-sulfo-3-bornylidenemethyl) benzene and / or its salts and / or the 2,4-bis - ⁇ [4- (2-ethyl-
- dibenzoylmethane derivatives for example the 4- (tert-butyl) -4'-methoxydibenzoylmethane
- Benzoxazole derivatives such as, in particular, 2,4-bis- [5-1 (dimethylpropyl) benzoxazol-2-yl- (4-phenyl) -imino] -6- (2-ethylhexyl) -imino-1 are also particularly advantageous according to the invention , 3,5-triazine with the CAS No. 288254-16-0, which is available, for example, under the trade name Uvasorb® K2A, and hydroxybenzophenones such as, in particular, the 2- (4'-diethylamino-2'-hydoxybenzoyl) benzoic acid hexyl ester or else Aminobenzophenone, which is available under the Uvinul A Plus.
- the preparations according to the invention advantageously contain the substances which absorb UV radiation in the UV-A and / or UV-B range in a total amount of, for. B. 0.1 wt .-% to 30 wt .-%, preferably 0.5 to 20 wt .-%, in particular 1, 0 to 15.0 wt .-%, each based on the total weight of the preparations to cosmetic
- 0.1 wt .-% to 30 wt .-% preferably 0.5 to 20 wt .-%, in particular 1, 0 to 15.0 wt .-%, each based on the total weight of the preparations to cosmetic
- formulations according to the invention can advantageously, although not necessarily, also be used in combination with UV radiation - be it with artificially generated or natural ultraviolet rays - for example in order to increase natural tanning or to achieve a particularly long-lasting tanning.
- the cosmetic and dermatological formulations according to the invention are applied to the skin and / or the hair in a sufficient amount in the manner customary for cosmetics.
- the use of the agent according to the invention in particular a cosmetic and / or dermatological preparation, is preferred - as an aqueous system and / or surfactant preparation for cleaning and care of the skin and / or hair,
- Hnhd-01938 (203-058-1) - as a multiple emulsion, microemulsion, Pickering emulsion or sprayable emulsion, - as a presun, a sunscreen or an aftersun formulation, - for topical use on skin and / or hair, - for tanning the skin, - for skin care, - for Protection of the skin and / or hair from damaging UV rays,. - to increase melanin synthesis in the skin,.
- the compounds according to the invention can likewise be a constituent of a polymer matrix, a skin and / or wound dressing, a plaster, a cloth or pad, a spray or on or in textiles, such as bandages or bath textiles.
- polymer matrices such as, for example, polyurethane matrices
- Active ingredient release - the compounds from the matrix can be released to the skin or hair and enable their advantageous properties there.
- the compounds In a plaster application or applied to textiles, bandages or the like, the compounds can penetrate the skin and bring about the desired protection, care or tanning effect.
- Hnhd-01938 (203-058-1) Water, VES (fully desalinated) ad 100.0 ad 100.0 ad 100.0 The pH is adjusted to 6.
Abstract
The invention relates to agents that are to be applied to the skin or hair, especially to increase tanning of the skin and melanin synthesis in the skin or hair. The invention particularly relates to cosmetic or dermatological preparations containing tetrasubstituted cyclohexene compounds. The inventive preparations are used for inducing and intensifying the tanning mechanisms of the skin, intensifying the hair color, and thus also boosting the intrinsic protection of the skin or hair.
Description
Haut- und/oder Haarmittel enthaltend 4-fach substituierte Cyclohexen- Verbindungen Skin and / or hair products containing 4-times substituted cyclohexene compounds
Die vorliegende Erfindung betrifft Mittel zur Anwendung auf der Haut und/oder dem Haar, insbesondere zur Steigerung der Hautbräunung sowie der Melanin-Synthese in der Haut oder dem Haar. Insbesondere umfasst die Erfindung kosmetische oder dermatologische - Zubereitungen enthaltend 4-fach substituierte Cyclohexen- Verbindungen. Die Verwendung der Zubereitungen führt zur Induktion und Intensivierung der Bräunungsmechanismen der Haut, zur Intensivierung der Haarfarbe und damit auch zu einer Steigerung des Haut- oder Haareigenschutzes.The present invention relates to agents for use on the skin and / or hair, in particular for increasing skin tanning and melanin synthesis in the skin or hair. In particular, the invention encompasses cosmetic or dermatological preparations containing 4-times substituted cyclohexene compounds. The use of the preparations leads to the induction and intensification of the tanning mechanisms of the skin, to the intensification of the hair color and thus also to an increase in skin or hair protection.
Die schädigende Wirkung des ultravioletten Teils der Sonnenstrahlung auf die Haut ist allgemein bekannt. Während Strahlen mit einer Wellenlänge, die kleiner als 290 nm ist (der so genannte UVG-Bereich), von der Ozonschicht in der Erdatmosphäre absorbiert werden, verursachen Strahlen im Bereich zwischen 290 nm und 320 nm, dem so genannten UVB-Bereich, ein Erythem, einen einfachen Sonnenbrand oder sogar mehr oder weniger starke Verbrennungen auf der Haut.The damaging effect of the ultraviolet part of solar radiation on the skin is well known. While rays with a wavelength shorter than 290 nm (the so-called UVG range) are absorbed by the ozone layer in the earth's atmosphere, rays in the range between 290 nm and 320 nm, the so-called UVB range, cause erythema , a simple sunburn or even more or less severe burns on the skin.
Zum Schütze gegen UVB-Strahlung sind zahlreiche Verbindungen bekannt, bei denen es sich zumeist um Derivate des 3-Benzylidencamphers, der 4-Aminobenzoesäure, der Zimtsäure, der Salicylsäure, des Benzophenons sowie auch des 2-Phenylbenzimidazols handelt.Numerous compounds are known for protecting against UVB radiation, most of which are derivatives of 3-benzylidene camphor, 4-aminobenzoic acid, cinnamic acid, salicylic acid, benzophenone and also 2-phenylbenzimidazole.
Auch für den Bereich zwischen etwa 320 nm und etwa 400 nm, den so genannten UVA- Bereich, ist es wichtig, Filtersubstanzen zur Verfügung zu haben, da auch dessen Strahlen S chäden h ervorrufen können. S o ist e rwiesen, d ass U VA-Strahlung zu einer Schädigung d er e lastischen u nd kollagenen F asern d es B indegewebes f ührt, was die Haut vorzeitig altern lässt, und dass sie als Ursache zahlreicher phototoxischer und photoallergischer Reaktionen zu sehen ist. Der schädigende Einfluss der UVB-Strahlung kann durch UV-A-Strahlung verstärkt werden.It is also important to have filter substances available for the range between about 320 nm and about 400 nm, the so-called UVA range, since their rays can also cause damage. It has been shown that U VA radiation damages the elastic and collagen fibers of the connective tissue, which causes the skin to age prematurely, and that it can be seen as the cause of numerous phototoxic and photoallergic reactions is. The damaging influence of UVB radiation can be intensified by UV-A radiation.
UVA-Strahlung kann ferner Hautschädigungen hervorrufen,. indem u. a. das hauteigene Keratin oder Elastin geschädigt wird. Hierdurch werden Elastizität und Wasserspei-UVA radiation can also cause skin damage. by u. a. the skin's own keratin or elastin is damaged. As a result, elasticity and water
' chervermögen der Haut reduziert, d.h. die Haut wird weniger geschmeidig und neigt zur Faltenbildung. Diese Art der Faltenbildung wird auch als lichtbedingte Hautalterung bezeichnet. Die auffallend hohe Hautkrebshäufigkeit in Gegenden starker Son- Hnhd-01938 (203-058-1)
neneinstrahlung zeigt, d ass offenbar auch Schädigungen der Erbinformationen in den Zellen durch Sonnenlicht hervorgerufen werden. 'Chervermögen the skin, ie the skin becomes less supple and tends to form wrinkles. This type of wrinkling is also known as light-related skin aging. The remarkably high incidence of skin cancer in areas of strong sun Hnhd-01938 (203-058-1) Irradiation shows that the genetic information in the cells is apparently also damaged by sunlight.
Die UV-Strahlung kann aber auch zu photochemischen Reaktionen führen, wobei dann die photochemischen Reaktionsprodukte in den Hautmetabolismus eingreifen.However, UV radiation can also lead to photochemical reactions, in which case the photochemical reaction products interfere with the skin's metabolism.
Vorwiegend handelt es sich bei solchen photochemischen Reaktionsprodukten um radikalische Verbindungen, z.B. Hydroxylradikale. Auch Undefinierte radikalische Photoprodukte, welche in der Haut selbst entstehen, können aufgrund ihrer hohen Reaktivität unkontrollierte Folgereaktionen an den Tag legen. Auch Singulettsauerstoff, ein nicht radikalisch angeregter Zustand des Sauerstoffmoleküls kann bei UV-Bestrahlung auftreten, ebenso kurzlebige Epoxide und viele Andere. Singulettsauerstoff beispielsweise zeichnet sich gegenüber dem normalerweise vorliegenden Triplettsauerstoff , (radikalischer Grundzustand) durch gesteigerte Reaktivität aus. Allerdings existieren auch angeregte, reaktive (radikalische) Triplettzustände des . Sauerstoffmoleküls. Derartige Vorgänge sind über oxidative Schädigung verschiedener Hautstrukturen ganz wesentlich an der lichtbedingten Hautalterung (u. a. Faltenbildung) beteiligt.Such photochemical reaction products are predominantly radical compounds, e.g. Hydroxyl radicals. Undefined radical photo products, which are created in the skin itself, can also display uncontrolled subsequent reactions due to their high reactivity. Singlet oxygen, a non-radically excited state of the oxygen molecule can also occur under UV radiation, as can short-lived epoxies and many others. Singlet oxygen, for example, is characterized by increased reactivity compared to the triplet oxygen that is normally present (radical ground state). However, there are also excited, reactive (radical) triplet states of the. Oxygen molecule. Such processes are very significantly involved in light-related skin aging (including wrinkling) due to oxidative damage to various skin structures.
Ferner zählt UV-Strahlung zur ionisierenden Strahlung. Es besteht also das Risiko, dass auch ionische Spezies bei UV-Exposition entstehen, welche dann ihrerseits oxidativ in die biochemischen Prozesse einzugreifen vermögen.UV radiation also belongs to ionizing radiation. There is therefore a risk that ionic species also develop when exposed to UV, which in turn can then oxidatively intervene in the biochemical processes.
Die P igmentierung der menschlichen Haut wird im wesentlichen durch die Gegenwart von Melanin bewirkt. Melanin und dessen Abbauprodukte (Melanoide), Carotin, der Durchblutungsgrad sowie die Beschaffenheit und Dicke des stratum comeum und ande- re Hautschichten lassen Hautfarbtöne von praktisch weiß (bei verringerter Füllung oder bei Fehlen der Blutgefäße) oder gelblich über hellbraun-rötlich, bläulich bis braun verschiedener Nuancen und schließlich beinahe schwarz erscheinen. Die einzelnen Hautregionen zeigen aufgrund unterschiedlicher Melanin-Mengen unterschiedliche Tiefe der Farbtönung.The pigmentation of human skin is essentially caused by the presence of melanin. Melanin and its breakdown products (melanoids), carotene, the degree of blood circulation and the nature and thickness of the stratum comeum and other skin layers leave skin tones of practically white (with reduced filling or in the absence of blood vessels) or yellowish over light brown-reddish, bluish to brown different shades and finally appear almost black. The individual skin regions show different depths of color due to different amounts of melanin.
Das natürliche Melanin schützt die Haut vor eindringender UV-Strahlung. Die Anzahl der in den Melanocyten produzierten Melanin-Granula entscheidet über Hell- oder Dunkelhäutigkeit. Bei starker Pigmentierung (z.B. bei Farbigen, aber auch bei Hellhäutigen nach längerer UV-Bestrahlung) ist Melanin auch im stratum spinosum und sogarThe natural melanin protects the skin from penetrating UV radiation. The number of melanin granules produced in the melanocytes determines whether the skin is light or dark. With strong pigmentation (e.g. in colored people, but also in fair-skinned people after prolonged UV radiation), melanin is also in the stratum spinosum and even
Hnhd-01938 (203-058-1)
im stratum corneum festzustellen. Es schwächt die UV-Strahlung um bis zu ca. 90%, bevor diese das Corium erreicht.Hnhd-01938 (203-058-1) in the stratum corneum. It weakens the UV radiation by up to approx. 90% before it reaches the corium.
Melanozyten enthalten als charakteristische Zellorganellen Melanosomen, in denen das Melanin gebildet wird. Unter anderem bei Anregung durch UV-Strahlung wird verstärkt Melanin gebildet. Dieses wird über die lebenden Schichten der Epidermis (Keratinozyten) letztlich in die Hornschicht (Corneozyten) transportiert und ruft die mehr oder weniger ausgeprägte bräunliche bis braun-schwarze Hautfarbe hervor. Melanin wird als Endstufe eines oxidativen Prozesses gebildet, in welchem Tyrosin unter Mitwirkung der Enzyms Tyrosinase über mehrere Zwischenstufen zu den braun bis braun-schwarzen Eumelaninen (DHICA- und DHI-Melanin) bzw. unter Beteiligung vpn schwefelhaltigen Verbindungen zunr rötlichen Phäomelanin umgewandelt. DHICA- und DHI-Melanin entstehen über die gemeinsamen Zwischenstufen Dopachinon und Dσpachrom. Letzteres wird, teilweise unter Beteiligung weiterer Enzyme, entweder in lndol-5,6-Chinon-Carbonsäure oder in lndol-5,6-Chinon umgesetzt, woraus die beiden genannten Eumelanine entstehen. Die Entstehung von Phäomelanin läuft unter anderem über die Zwischenprodukte Dopachinon und Cysteinyldopa.As characteristic cell organelles, melanocytes contain melanosomes, in which the melanin is formed. When stimulated by UV radiation, among other things, melanin is increasingly formed. This is ultimately transported into the horny layer (corneocytes) via the living layers of the epidermis (keratinocytes) and causes the more or less pronounced brown to brown-black skin color. Melanin is formed as the final stage of an oxidative process in which tyrosine, with the help of the enzyme tyrosinase, is converted into brown to brown-black eumelanins (DHICA and DHI melanin) or with the participation of sulfur-containing compounds to reddish pheomelanin with the help of the enzyme tyrosinase. DHICA and DHI melanin are produced via the common intermediate stages dopaquinone and dσpachrom. The latter is implemented, partly with the participation of further enzymes, either in indole-5,6-quinone carboxylic acid or in indole-5,6-quinone, from which the two eumelanins mentioned arise. The formation of phaeomelanin occurs among other things via the intermediates dopaquinone and cysteinyldopa.
Neben verschiedenen Funktionen des hauteigenen Melanins, wie beispielsweise "Entgiftung'VBindung von toxischen Substanzen/Pharmaka usw., ist die Funktion von Melanin als natürlicher UV-Filter zum Schutz vor schädigenden UV-Strahlen sowie die Antioxidansfunktion von Melanin als Schutz vor reaktiven Sauerstoffspezies (oxidativem Stress), die unter anderem durch Sonnenstrahlung auftreten können, für die Haut sehr wichtig. Dies auch in Bezug auf die Homöostase, Vermeidung von Hautalterung, Vermeidung von Sonnenbrand usw. Somit sollte sich nicht nur ein kosmetischer Nutzen im Sinne einer verstärkte Bräunung durch die gesteigerte Melanin-Synthese in der Haut nach topischer Applikation von die Melanogenese steigernder Verbindungen ergeben sondern auch ein zusätzlicher Schutz durch die verschiedenen Schutzleistungen von Melanin.In addition to various functions of the skin's own melanin, such as "detoxification'V connection of toxic substances / pharmaceuticals etc., the function of melanin as a natural UV filter to protect against damaging UV rays and the antioxidant function of melanin as protection against reactive oxygen species (oxidative Stress), which can occur due to solar radiation, among other things, is very important for the skin, also with regard to homeostasis, avoidance of skin aging, avoidance of sunburn, etc. This should not only result in a cosmetic benefit in the sense of increased tanning due to the increased Melanin synthesis in the skin after topical application of compounds which increase the melanogenesis result in additional protection through the various protective functions of melanin.
Aufgabe der vorliegenden Erfindung ist es daher ein Mittel, insbesondere eine kosmetische oder dermatologische Zubereitung, zur Verfügung zu stellen, die die natürliche Bräunung der Haut durch gesteigerte Melanin-Synthese verstärkt und gleichzeitig zu einem gesteigerten Hauteigenschutz führt.The object of the present invention is therefore to provide an agent, in particular a cosmetic or dermatological preparation, which enhances the natural tanning of the skin by means of increased melanin synthesis and at the same time leads to an increased protection of the skin.
Je nach Lichtempfindlichkeit werden in der Regel folgende Hauttypen unterschieden:Depending on the sensitivity to light, the following skin types are generally distinguished:
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Hauttyp I bräunt nie, bekommt immer einen Sonnenbrand. Hauttyp II bräunt kaum, bekommt leicht einen Sonnenbrand. Hauttyp III bräunt durchschnittlich gut. Hauttyp IV bräunt leicht und anhaltend, bekommt fast nie Sonnenbrand. Hauttyp V dunkle, oft fast schwarze Haut, bekommt nie Sonnenbrand.Hnhd-01938 (203-058-1) Skin type I never tans, always gets a sunburn. Skin type II hardly tans, easily gets a sunburn. Skin type III tans well on average. Skin type IV tans lightly and persistently, almost never gets sunburned. Skin type V dark, often almost black skin, never gets sunburned.
Die natürliche Abschirmung der schädlichen UV-Strahlung ist ein handfester Vorteil der natürlichen Hautbräunung. Seit einigen Jahrzehnten gilt darüber hinaus eine „gesunde" Hautfarbe als Zeichen von insbesondere sportlicher Aktivität und wird daher von einer breiten Verbraucherschicht als erstrebenswert erachtet. Vertreter der Hauttypen I und II, die sich einer solchen Hauttönung erfreuen wollen, sind daher ohnehin auf selbstbräunende Präparate angewiesen. Aber auch Vertreter des Hauttyps III, die sich nicht allzu sehr den Risiken des Sonnenbades aussetzen und trotzdem gebräunt aus- sehen wollen, sind dankbare Zielgruppen für selbstbräunende Zubereitungen.The natural shielding of harmful UV radiation is a tangible advantage of natural skin tanning. For several decades, a "healthy" skin color has also been a sign of sporting activity in particular and is therefore considered desirable by a wide range of consumers. Representatives of skin types I and II who want to enjoy such a skin tint are therefore dependent on self-tanning preparations anyway But representatives of skin type III who are not too exposed to the risks of sunbathing and still want to look tanned are grateful target groups for self-tanning preparations.
Die einfachste Art und Weise, seiner Haut einen braunen Farbton zu verleihen, ist das Auftragen entsprechend gefärbter Schminken oder Make-up-Präparate. Allerdings werden selbstverständlich nur solche Körperpartien angefärbt, die von den farbigen Präpa- raten ü berdeckt werden. Mit Hilfe abwaschbarer Make-up-Präparate kann eine leichte Hauttönung erzielt werden (z.B. Extrakte aus frischen grünen Walnussschalen, Henna). Ein Nachteil der Schminken ist deshalb die zeitraubende Prozedur des Auftragens. Ferner nachteilig ist, dass sie stark auf Textilien wie Hemdkragen oder Blusen abfärben. Darüber hinaus können die verschiedenen Farbstoffe unterschiedliche alfefgene Potenz aufweisen und sogar hautirritierend wirken.The easiest way to give your skin a brown hue is to apply appropriately colored make-up or make-up preparations. However, only those parts of the body that are covered by the colored preparations are of course stained. With the help of washable make-up preparations, a light skin tint can be achieved (e.g. extracts from fresh green walnut shells, henna). A disadvantage of the make-up is therefore the time-consuming procedure of applying. Another disadvantage is that they rub off heavily on textiles such as shirt collars or blouses. In addition, the different dyes can have different alfefgenen potency and even irritate the skin.
Aufgabe der vorliegenden Erfindung ist es daher auch, Zubereitungen zur Verfügung zu stellen, die die Nachteile von Schmink-Bräunungszubereitungen nicht aufweisen.The object of the present invention is therefore also to provide preparations which do not have the disadvantages of make-up tanning preparations.
Künstliche Hautbräunung lässt sich auf kosmetischem bzw. medizinischem Wege bewirken, wobei im wesentlichen folgende Ansätze eine Rolle spielen:Artificial skin tanning can be achieved by cosmetic or medical means, whereby the following approaches play a role:
Durch regelmäßige Einnahme von Carotin-Präparaten wird Carotin wird im Unterhaut- Fettgewebe gespeichert, die Haut färbt sich allmählich orange bis gelbbraun.By taking carotene supplements regularly, carotene is stored in the subcutaneous fatty tissue, the skin gradually turns orange to yellow-brown.
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Die Anfärbung kann auch auf dem Wege der chemischen Veränderung der Homschicht der Haut mit so genannten selbstbräunenden Zubereitungen erfolgen. Wichtigster Wirkstoff ist das Dihydroxyaceton (DHA). Die auf diese Weise erzielte Hautbräunung ist nicht abwaschbar und wird erst mit der normalen Abschuppung der Haut (nach ca. 10- 15 T agen) e ntfernt. D ihydroxyaceton k ann a Is K etotriose b ezeichnet w erden und reagiert als reduzierender Zucker mit den Aminosäuren der Haut bzw. den freien Amino- und I mino-Gruppen d es Keratins ü ber e ine R eihe von Zwischenstufen im Sinne einer Maillard-Reaktion zu braungefärbten Stoffen, so genanten Melanoiden, welche gelegentlich auch Melanoidine genannt werden. Ein besonderer Nachteil der Bräunung mit Dihydroxyaceton liegt darin, dass die mit ihm gebräunte Haut im Gegensatze zu „sonnengebräunter" Haut nicht gegen Sonnenbrand geschützt ist.Hnhd-01938 (203-058-1) The staining can also be done by chemical modification of the skin's skin layer with so-called self-tanning preparations. The most important active ingredient is dihydroxyacetone (DHA). The skin tanning achieved in this way cannot be washed off and is only removed with the normal desquamation of the skin (after approx. 10-15 days). Hydroxyacetone can be called etotriose and reacts as a reducing sugar with the amino acids of the skin or the free amino and i mino groups of keratin via a series of intermediates in the sense of a Maillard reaction to brown-colored substances, so-called melanoids, which are sometimes also called melanoidins. A particular disadvantage of tanning with dihydroxyacetone is that the skin tanned with it, in contrast to "sun-tanned" skin, is not protected against sunburn.
Ein weiterer Nachteil von Dihydroxyaceton besteht darin, dass es insbesondere unter dem Einfluss ultravioletter Strahlung, wenn auch in meist geringen Mengen, Formalde- hyd abspaltet. Es war daher ein dringender Bedarf Wege aufzuweisen, auf welchen der Zersetzung von Dihydroxyaceton wirksam begegnet werden kann.Another disadvantage of dihydroxyacetone is that it releases formaldehyde, in particular under the influence of ultraviolet radiation, even if mostly in small amounts. It was therefore an urgent need to have ways in which the decomposition of dihydroxyacetone can be effectively countered.
Eine Aufgabe der vorliegenden Erfindung ist es Alternativen zu DHA als Selbstbräunungsmittel zu finden, die keine nachteiligen Eigenschaften aufweisen wie sie bei DHA bekannt sind.An object of the present invention is to find alternatives to DHA as a self-tanning agent which do not have any disadvantageous properties, as are known from DHA.
Die Anfärbung durch Selbstbräuner erfolgt ohne Sonnenlichteinwirkung. Im Gegensatz dazu werden auch so genannte „Pre-Tan-Produkte" oder „Tan-Promoter" angeboten, die vor der Sonnenbestrahlung aufgetragen werden müssen, in der*"Söhne~ tritt dann eine' Vergilbung dieser Zubereitungen ein, die zu einer leichten Braungelb-Färbung der Oberhaut führen soll, welche die „Sonnenbräune" zusätzlich verstärkt.Staining by self-tanners takes place without exposure to sunlight. In contrast to this, so-called "pre-tan products" or "tan promoters" are also offered, which must be applied before sun exposure. In the * " sons ~ " these preparations then yellow, resulting in a light brown-yellow Coloring of the epidermis should lead, which additionally strengthens the "tan".
US 5093360 beschreibt kosmetische oder pharmazeutische Zubereitungen, die Retinal (Vitamin A aldehyd) und/oder deren Derivate enthalten. Retinal oder deren Derivate werden darin in Kombination mit aktiven Agentien oder als Additive i n verschiedenen Zubereitungen eingesetzt, um dermatologische Fehlsteuerungen zu beheben. Neben der Behandlung von Akne werden u.a. auch Tanning-Zubereitungen genannt, die neben den Tanning-Agentien als Zusatz Retinal oder deren Derivate enthalten. Ein Hinweis, dass Retinal oder deren Derivate alleine einen Effekt auf die Hautbräunung ausübt, wird nicht gegeben.US 5093360 describes cosmetic or pharmaceutical preparations which contain retinal (vitamin A aldehyde) and / or their derivatives. Retinal or its derivatives are used in combination with active agents or as additives in various preparations to remedy dermatological errors. In addition to the treatment of acne, i.a. also called tanning preparations which contain retinal or their derivatives in addition to the tanning agents. There is no indication that retinal or its derivatives alone have an effect on skin tanning.
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Eine weitere, von UV-Licht ebenfalls völlig unabhängige Art der künstlichen Bräunung kann durch die Hormone herbeigeführt werden, die im Körper auch infolge (natürlicher) UV-Bestrahlung üblicherweise freigesetzt werden und die Melanozyten letztlich zur Melanin-Synthese anregen. Zu nennen wären in diesem Zusammenhang beispielsweise 5 Abkömmlinge von Proopiomelanocortin (POMC) wie aMSH und synthetische Varianten (wie N DP), d ie zum Teil weitaus höhere Aktivität als das natürliche aMSH aufweisen. Zwar kann durch diese Hormone grundsätzlich eine Bräunung herbeigeführt werden, jedoch verbietet sich ihr Einsatz in Kosmetika, da es sich eindeutig um pharmakologisch wirkende Substanzen (Hormone) handelt* welche nicht ohne medizinische Indikation 10 breit eingesetzt werden sollten.Hn d-01938 (203-058-1) Another type of artificial tanning, which is also completely independent of UV light, can be brought about by the hormones which are also released in the body as a result of (natural) UV radiation and ultimately stimulate the melanocytes to synthesize melanin. In this context, five descendants of proopiomelanocortin (POMC) such as aMSH and synthetic variants (such as N DP) should be mentioned, for example, which in some cases have much higher activity than natural aMSH. Although these hormones can generally bring about a tan, their use in cosmetics is forbidden since they are clearly pharmacologically active substances (hormones) * which should not be used widely without medical indication.
Den Nachteilen des Standes der Technik abzuhelfen, war ebenso Aufgabe der vorliegenden Erfindung.To remedy the disadvantages of the prior art was also an object of the present invention.
15. In der Kosmetik ist neben der Hautgesundheit und der Hautpflege auch die Haarpflege ein äußerst intensiv erforschter Bereich.15. In cosmetics, in addition to skin health and skin care, hair care is an extremely intensively researched area.
Haar ist das aus Hörn bestehende, fadenförmige, fast universelle (an Handflächen, Fußsohlen, . Streckseiten der Zehen-, Fingerendglieder fehlende) Hautanhangsgebilde;Hair is the thread-like, almost universal (attached to the palms of the hands, soles of the feet, extensor sides of the toe and end of the fingers) skin appendages;
20 unterschieden als Langhaar (die Kopf-, Bart-, Achsel-, Schamhaare = Capilli, Barba, Hirci bzw. Pubes; beim Mann auch Brusthaar), Kurz-, Borstenhaar (Supercilia, Cilia, Vibrissae, Tragi) und Wollhaar (Lanugo, Velushaar). Der Aufbau all dieser Haare ist im groben und ganzen ähnlich: zentral das Haarmark (aus Epithelzellen mit eosinophilen Homsubstanzkörnchen = Trichohyalin-Granula), umgeben von der Haarrinde (aus20 differentiated as long hair (the head, beard, armpit, pubic hair = Capilli, Barba, Hirci or Pubes; in men also chest hair), short, bristle hair (Supercilia, Cilia, Vibrissae, Tragi) and wool hair (Lanugo, vellus). The structure of all of these hairs is roughly similar: the central hair mark (made of epithelial cells with eosinophilic granules = trichohyalin granules), surrounded by the hair cortex (from
25 verhornten Zellen; enthält Pigmente) und dem Haaroberhäutchen (Cuticula pili; kernlose Epidermisschicht) sowie von Schichten der epithelialen und bindegewebigen Haarscheide.25 horny cells; contains pigments) and the cuticle (cuticle pili; seedless epidermis layer) as well as layers of the epithelial and connective tissue hair sheath.
Das Haar gliedert sich in den aus der Haut ragenden Haarschaft und die in die 30 Unterhaut reichende, s chräge H aarwurzel, deren Schichten etwa denen der Oberhaut entsprechen . Das verdickte untere Wurzelende, die Haarzwiebel, sitzt einem in sie hineinragenden, gefäßhaltigen Bindegewebszapfen, der Haarpapille, auf (beide als Haarboden). Die Zwiebel ist in der Anfangs- ( = Anagen-) phase, der sich zyklisch wiederholenden Haarbildung zwiebelartig geschichtet infolge ständiger Neubildung von 35 Zellen durch ihre papillennahe Schicht (Matrix), später dann geschlossen, kolbig, ganzThe hair is divided into the hair shaft protruding from the skin and the sloping hair root reaching into the subcutis, the layers of which correspond approximately to those of the epidermis. The thickened lower end of the root, the hair bulb, sits on a vascular connective tissue cone, the hair papilla, protruding into it (both as a hair floor). The onion is in the initial (= anagen) phase, the cyclically repeating hair formation layered onion-like as a result of constant new formation of 35 cells by its layer close to the papilla (matrix), later closed, bulbous, whole
Hnhd-01938 (203-058-1)
verhornt (Kolbenhaar) und wird schließlich, in der End- ( = Telogen-) phase, durch ein neues Haar - ausgehend von einer sich neu bildenden Haarpapille - in Richtung Follikelöffnung verdrängt.Hnhd-01938 (203-058-1) cornified (piston hair) and is finally, in the final (= telogen) phase, displaced by a new hair - starting from a newly formed hair papilla - towards the follicle opening.
Verantwortlich für die persönliche Haarfarbe ist das Melanin. Gebildet wird das Melanin in den Melanozyten, Zellen, die in der Haarzwiebel assoziiert mit den Keratinozyten des Haarmarks vorkommen. Melanozyten enthalten - als charakteristische Zellorganellen Melanosomen, in denen das Melanin gebildet wird. Dieses wird über die langen Dendriten der Melanozyten in die Keratinozyten der präkortikalen Matrix transferiert und ruft die mehr oder weniger ausgeprägte blonde bis braun-schwarze Haarfarbe hervor. Melanin wird als Endstufe eines oxidativen Prozesses gebildet, in welchem Tyrosin unter Mitwirkung der Enzyms Tyrosinase über mehrere Zwischenstufen zu den braun bis braun-schwarzen Eumelaninen (DHICA- und DHI-Melanin) bzw. unter Beteiligung von . schwefelhaltigen Verbindungen zum rötlichen Phäomelanin umgewandelt wird. DHICA- und DHI-Melanin entstehen über die gemeinsamen Zwischenstufen Dopachinon und Dopach rom. Letzteres wird, teilweise unter Beteiligung weiterer Enzyme, entweder in lndol-5,6-Chinon-Carbonsäure oder in lndol-5,6-Chinon umgesetzt, woraus die beiden genannten Eumelanine entstehen. Die Entstehung von Phäomelanin läuft unter anderem über die Zwischenprodukte Dopachinon und Cysteinyldopa. Cystein wird zusätzlich nötig, wenn das Phaeomelanin für blonde und rötliche Haare entstehen soll.Melanin is responsible for the personal hair color. Melanin is formed in the melanocytes, cells that occur in the hair bulb in association with the keratinocytes of the hair market. Melanocytes contain - as characteristic cell organelles - melanosomes in which the melanin is formed. This is transferred via the long dendrites of the melanocytes into the keratinocytes of the precortical matrix and creates the more or less pronounced blonde to brown-black hair color. Melanin is formed as the final stage of an oxidative process, in which tyrosine with the help of the enzyme tyrosinase via several intermediate stages to the brown to brown-black eumelanins (DHICA and DHI melanin) or with the participation of. sulfur-containing compounds is converted to reddish phaeomelanin. DHICA and DHI melanin are produced via the common intermediate stages dopaquinone and dopach rom. The latter is converted, partly with the participation of further enzymes, either into indole-5,6-quinone carboxylic acid or into indole-5,6-quinone, from which the two called Eumelanine arise. The formation of phaeomelanin occurs among other things via the intermediates dopaquinone and cysteinyldopa. Cysteine is also necessary if the phaeomelanin is to be created for blonde and reddish hair.
Das Eumelanin ist das Schwarz-Braun-Pigment. Es entscheidend hauptsächlich über die Farbtiefe des Haares. In braunem und schwarzem Haar kommt es in deutlich erkennbaren Körnchen vor.Eumelanin is the black-brown pigment. It is mainly about the depth of color of the hair. In brown and black hair it occurs in clearly recognizable granules.
Das Phaeomelanin ist das Rot-Pigment. Es ist verantwortlich für hellblonde, blonde und rote Haare. Dieses Melanin ist von seiner Struktur her sehr viel feiner und kleiner. Aus den verschiedenen Anteilen der Melanintypen entstehen die verschiedenen Haarfarben: • Blondes Haar enthält wenig Eumelanin und viel Phaeomelanin. • Dunkles Haar enthält viel Eumelanin und wenig Phaeomelanin. • Rotes Haar hat ebenfalls wenig Eumelanin und sehr viel Phaeomelanin. • Alle dazwischenliegenden Haarschattierungen entstehen aus unterschiedlichen Mischungsverhältnissen der beiden Melanintypen.Phaeomelanin is the red pigment. It is responsible for light blonde, blonde and red hair. The structure of this melanin is much finer and smaller. The different hair colors result from the different proportions of the melanin types: • Blond hair contains little eumelanin and a lot of phaeomelanin. • Dark hair contains a lot of eumelanin and little phaeomelanin. • Red hair also has little eumelanin and a lot of phaeomelanin. • All shades of hair in between result from different mixing ratios of the two melanin types.
Hnhd-01938 (203-058-I)
Ablaufen kann der Pigmentbildungsprozeß nur, wenn genügend Tyrosinase zur Verfügung steht. Dieses Enzym wird mit zunehmendem Alter seltener gebildet. Das führt dann nach und nach zur grauen Haaren. Der Grund: mit wenig Tyrosinase wird auch immer weniger Tyrosin gebildet. So nimmt auch die Produktion von Melanin ab. Das fehlende Melanin wird durch die Einlagerung von Luftbläschen ersetzt. Die Haare erscheinen grau.Hnhd-01938 (203-058-I) The pigment formation process can only proceed if sufficient tyrosinase is available. This enzyme is produced less frequently with age. This gradually leads to gray hair. The reason: with little tyrosinase, less and less tyrosine is formed. The production of melanin also decreases. The missing melanin is replaced by the storage of air bubbles. The hair appears gray.
Dieser Prozess ist in der Regel schleichend. Er beginnt an den Schläfen und weitet sich dann auf die gesamte Kopfbehaarung aus. Danach erwischt es den Bart und die Augenbrauen. Zuletzt sind schließlich alle Haare des Körpers grau.This process is usually insidious. It begins at the temples and then extends to the entire hair on the head. Then it hits the beard and eyebrows. Finally, all of the body's hair is gray.
Medizinisch werden graue Haare als Canities bezeichnet. Es gibt verschiedene Möglichkeiten des Ergrauens. Vorzeitiges Ergrauen, ab dem 20 Lebensjahr, nennt sich auch Canities praecox.Medically, gray hair is called canities. There are several ways of graying. Premature graying, from the age of 20, is also called Canities praecox.
Die Canities symptomatica, oder symptomatisches Ergrauen der Haare, kann verschiedene Ursachen haben. Dazu gehören: Perniziöse Anämie (Vitamin-B-Mangelanämie), schwere endokrinologische Störungen, z. B. bei Schilddrüsenerkrankungen. akute, fieberhafte Erkrankungen, Arzneimittelnebenwirkungen, Kosmetika, Metalle.Symptoms of canities, or symptomatic graying of the hair, can have various causes. These include: Pernicious anemia (vitamin B deficiency anemia), severe endocrinological disorders, e.g. B. in thyroid diseases. acute, febrile diseases, drug side effects, cosmetics, metals.
Die Färbung von Haaren, insbesondere von lebenden menschlichen Haaren, mit Hilfe natürlicher Farbstoffe, wie dies seit dem Altertum insbesondere für den Farbstoff Henna bekannt ist, und die seit Jahren zugunsten synthetischer Farbstoffe in den Hintergrund gedrängt wurden, b ildet s eit e inigen J ahren den Gegenstand eines neuen Interesses. Nachteilig ist der durch Henna entstehende rote Farbton.The coloring of hair, especially of living human hair, with the help of natural dyes, as has been known for the dye henna since ancient times, and which has been pushed into the background for years in favor of synthetic dyes, has been taking place for several years the subject of a new interest. A disadvantage is the red color created by henna.
Mit zunehmendem Lebensalter nimmt die Melaninproduktion ab, die die Haarfarbe bewirkt: die Haare werden grau bzw. weiß. Es ist ein kosmetischer Wunsch bei einigen Verbrauchern, diesen Prozess umzukehren bzw. langsamer ablaufen zu lassen. Hierzu verwendet die kosmetische Industrie in einigen Ländern Bleiacetat, das giftig ist und daher in der europäischen Kosmetikverordnung verboten ist. Dieses Bleiacetat wirdWith increasing age, the melanin production that causes the hair color decreases: the hair becomes gray or white. It is a cosmetic wish of some consumers to reverse this process or to let it run more slowly. For this purpose, the cosmetic industry uses lead acetate in some countries, which is toxic and is therefore prohibited in the European Cosmetics Regulation. This lead acetate will
Hπhd-01938 (203-058-1)
vorzugsweise als Lösung auf die Haare aufgebracht und verbleibt dort längere Zeit, ohne abgewaschen zu werden.Hπhd-01938 (203-058-1) preferably applied to the hair as a solution and remains there for a long time without being washed off.
Für das Färben von keratinhaltigen Fasern, z. B. Haaren, Wolle oder Pelzen, kommen im allgemeinen entweder direktziehende Farbstoffe oder Oxidationsfarbstoffe, die durch oxidative Kupplung einer oder mehrerer Entwicklerkomponenten untereinander oder mit einer oder mehreren Kupplerkomponenten entstehen, zur Anwendung. Kuppler- und Entwicklerkomponenten werden auch als Oxidationsfarbstoffvorprodukte bezeichnet.For dyeing keratin fibers, e.g. B. hair, wool or fur, generally either direct dyes or oxidation dyes, which are formed by oxidative coupling of one or more developer components with one another or with one or more coupler components, are used. Coupler and developer components are also referred to as oxidation dye precursors.
Als Entwicklerkomponenten werden üblicherweise primäre aromatische Amine mit einer weiteren, in para- oder ortho-Position befindlichen freien oder substituierten Hydroxy- oder Aminogruppe, Diaminopyridinderivate, heterocyclische Hydrazone, 4-Aminopyrazo- londerivate sowie 2,4,5,6-Tetraaminopyrimidin und dessen Derivate eingesetzt.Primary aromatic amines with a further free or substituted hydroxy or amino group in the para or ortho position, diaminopyridine derivatives, heterocyclic hydrazones, 4-aminopyrazone derivatives and 2,4,5,6-tetraaminopyrimidine and derivatives thereof are usually used as developer components used.
Spezielle Vertreter sind beispielsweise p-Phenylendiamin, p-Toluylendiamin, 2,4,5,6- Tetraaminopyrimidin, p-Aminophenol, N,N-Bis-(2-hydroxyethyl)-p-phenylendiamin, 2- (2,5-Diaminophenyl)-ethanol, 2-(2,5-Diaminophenoxy)-ethanol, 1- Phenyl-3- carboxyamido-4-amino-pyrazolon-5, 4-Amino-3-methylphenol, 2-Aminomethyl-4- aminophenol, 2-Hydroxymethyl-4-aminophenol, 2-Hydroxy-4,5,6-triaminopyrimidin, 2,4- Dihydroxy-5,6-diaminopyrimidin und 2,5,6-Triamino-4-hydroxypyrimidin.Specific representatives are, for example, p-phenylenediamine, p-toluenediamine, 2,4,5,6-tetraaminopyrimidine, p-aminophenol, N, N-bis- (2-hydroxyethyl) -p-phenylenediamine, 2- (2,5-diaminophenyl ) -ethanol, 2- (2,5-diaminophenoxy) -ethanol, 1-phenyl-3-carboxyamido-4-amino-pyrazolon-5, 4-amino-3-methylphenol, 2-aminomethyl-4-aminophenol, 2- Hydroxymethyl-4-aminophenol, 2-hydroxy-4,5,6-triaminopyrimidine, 2,4-dihydroxy-5,6-diaminopyrimidine and 2,5,6-triamino-4-hydroxypyrimidine.
Als Kupplerkomponenten werden in der Regel m-Phenylendiaminderivate, Naphthole, Resorcin und Resorcinderivate, Pyrazolone und m-Aminophenole verwendet. Als Kupplersubstanzen eignen sich insbesondere α-Naphthol, 1 ,5-, 2,7- und 1 ,7-Dihydroxy- naphthalin, 5-Amino-2-methylphenol, m-Aminophenol, Resorcin, Resorcin- monomethylether, m-Phenylendiamin, 2,4-diamin.ophenoxyethanol, 1- P henyl-3-methyl- pyrazolon-5, 2,4-DichIor-3-aminophenol, 1 ,3-Bis-(2,4-diaminophenoxy)-propan, 2- Chlorresorcin, 4-Chlorresorcin, 2-Chlor-6-methyl-3-aminophenol, 2-Methylresorcin und 5-Methylresorcin.M-Phenylenediamine derivatives, naphthols, resorcinol and resorcinol derivatives, pyrazolones and m-aminophenols are generally used as coupler components. Suitable coupler substances are, in particular, α-naphthol, 1, 5-, 2,7- and 1, 7-dihydroxynaphthalene, 5-amino-2-methylphenol, m-aminophenol, resorcinol, resorcinol monomethyl ether, m-phenylenediamine, 2 , 4-diamine . ophenoxyethanol, 1-phenyl-3-methyl-pyrazolon-5, 2,4-dichloro-3-aminophenol, 1, 3-bis (2,4-diaminophenoxy) propane, 2-chlororesorcinol, 4-chlororesorcinol, 2 -Chlor-6-methyl-3-aminophenol, 2-methylresorcinol and 5-methylresorcinol.
Bezüglich weiterer üblicher Farbstoffkomponenten wird ausdrücklich auf die Reihe "Dermatology", herausgeben von Ch. Culnan, H. Maibach, Verlag Marcel Dekker Inc., New York, Basel, 1986, Bd. 7, Ch. Zviak, The Science of Hair Care, Kap. 7, Seiten 248- 250 (Direktziehende Farbstoffe), und Kap. 8, Seiten 264-267 (Oxidationsfarbstoffe), sowie das "Europäische Inventar der Kosmetikrohstoffe", 1996, herausgegeben von derWith regard to other conventional dye components, reference is expressly made to the "Dermatology" series, edited by Ch. Culnan, H. Maibach, Verlag Marcel Dekker Inc., New York, Basel, 1986, Vol. 7, Ch. Zviak, The Science of Hair Care, Cape. 7, pages 248-250 (direct dyes), and chap. 8, pages 264-267 (oxidation dyes), as well as the "European inventory of cosmetic raw materials", 1996, published by the
Hnhd-01938 (203-058-1)
Europäischen Kommission, erhältlich in Diskettenform vom Bundesverband der deutschen Industrie- und Handelsunternehmen für Arzneimittel, Reformwaren und Körperpflegemittel e.V., Mannheim, Bezug genommen.Hnhd-01938 (203-058-1) European Commission, available in diskette form from the Federal Association of German Industry and Commerce for Medicinal Products, Health Care Products and Personal Care Products, Mannheim.
Mit Oxidationsfarbstoffen lassen sich zwar intensive Färbungen mit guten Echtheitseigenschaften erzielen, die Entwicklung der Farbe geschieht jedoch im allgemeinen unter dem Einfluss von Oxidationsmitteln wie z. B. H202, was in einigen Fällen Schädigungen der Faser zur Folge haben kann. Des weiteren können einige Oxidationsfarbstoffvorprodukte bzw. v bestimmte Mischungen von Oxidationsfarbstoffvorprodukten bisweilen bei Personen mit empfindlicher Haut sensibilisierend wirken. Direktziehende Farbstoffe werden unter schonenderen Bedingungen appliziert, ihr Nachteil liegt jedoch darin, dass die Färbungen häufig nur über unzureichende Echtheitseigenschaften verfügen.With oxidation dyes intensive dyeings can be achieved with good fastness properties, but the development of the color is generally done under the influence of oxidizing agents such. B. H 2 0 2 , which in some cases can result in damage to the fiber. Furthermore, some oxidation dye precursors or v certain mixtures of oxidation dye precursors can have a sensitizing effect sometimes in people with sensitive skin. Direct dyes are applied under gentler conditions, but their disadvantage is that the dyeings often have inadequate fastness properties.
Aufgabe der vorliegenden Erfindung ist es die selbständige Melaninproduktion der Haare zu verbessern, ohne jedoch auf Färbungsmitteln und insbesondere Oxidationsmittel wie z . B . H2O2 angewiesen zu sein. Darüber hinaus dürfen die Mittel kein oder lediglich ein sehr geringes Sensibilisierungspotential aufweisen.The object of the present invention is to improve the independent melanin production of the hair, but without coloring agents and in particular oxidizing agents such. B. H 2 O 2 to be instructed. In addition, the agents must have no or only a very low sensitization potential.
Es wurde nun überraschenderweise gefunden dass ein Mittel nach Anspruch 1 insbesondere kosmetische oder dermatologische Zubereitungen nach einem derIt has now surprisingly been found that an agent according to claim 1 in particular cosmetic or dermatological preparations according to one of the
Ansprüche 3 bis 14 das gesamte Bündel an Aufgaben löst.Claims 3 to 14 solve the entire set of tasks.
Gegenstand der Unteransprüch.e sind vorteilhafte Ausführungsformen der erfindungsgemäßen Mittel. Des weiteren— umfasst- die Erfindung die Verwendung- derartiger Mittel sowie die erfindungsgemäßen Verbindungen als Mittel zur Steigerung der Hautbräune bzw. der Melaninsynthese in der Haut oder dem Haar.Subject of the subclaim . e are advantageous embodiments of the agents according to the invention. Furthermore, the invention includes the use of such agents and the compounds according to the invention as agents for increasing the tan or the melanin synthesis in the skin or hair.
Es war ü berraschend u nd für den Fachmann nicht vorauszusehen, dass kosmetische oder dermatologische Z ubereitungen e nthaltend e ine o der m ehrere V erbindungen d er StrukturIt was surprising and unforeseeable for the person skilled in the art that cosmetic or dermatological preparations contain one or more compounds of the structure
Hnhd-01938 (203-058-1)
nachfolgend als 4-fach substituierte Cyclohexen-Verbindungen bezeichnet, die Aufgaben lösen. Wobei die ResteHnhd-01938 (203-058-1) hereinafter referred to as 4-times substituted cyclohexene compounds that solve the problems. With the leftovers
- R1 , R2 und/oder R5 gewählt werden aus der Gruppe Wasserstoff, Methyl, Ethyl, Propyl, iso-Propyl, Butyl, tert-Butyl, Hydroxymethyl, Hydroxyethyl, Hydroxypropyl, Hydroxy u nd/oder Carbonsäurealkylester mit Alkylresten gewählt aus Methyl, Ethyl, Propyl oder Butyl, bevorzugt Ist Methyl;- R1, R2 and / or R5 are selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxy and / or alkyl carboxylates with alkyl radicals selected from methyl, ethyl , Propyl or butyl, preferably is methyl;
- R3 gewählt wird aus der Gruppe der Verbindungsreste der Struktur (I) mit (D- R3 is selected from the group of connection residues of structure (I) with (D
R6 und/oder R7 gewählt werden aus der Gruppe Methyl, Wasserstoff, Ethyl, Propyl, iso-Propyl, Butyl, tert-Butyl, Hydroymethyl, Hydroxyethyl, Hydroxypropyl, Hydroxy oder Carbonsäurealkylester, wobei der Alkylrest gewählt wird aus Methyl, Ethyl, Propyl oder Butyl, bevorzugt ist Methyl; R4 gewählt wird aus Carbonylsauerstoff, - Aminosäureresten Ala, Ser, Gly, Val, Leu, lle, Pro, Trp, Phe, Met Tyr, Thr, Cys, Asn, Asp, Glu, Lys, Arg, Gin, H, Orn, Sar, Hyl, Hyp, Hse oder Hey, bevorzugt Ala, Ser oder Gly, - Resten der Struktur N-(CH2)x-OH, N-(CHR9)x-CH2OH, N-(CH2)x-OCOMe, wobei jeweils x = 1 - 1 0, N-OH, oder - Resten der Struktur R6 and / or R7 are selected from the group consisting of methyl, hydrogen, ethyl, propyl, isopropyl, butyl, tert-butyl, hydroymethyl, hydroxyethyl, hydroxypropyl, hydroxy or alkyl carboxylate, the alkyl radical being selected from methyl, ethyl, propyl or Butyl, methyl is preferred; R4 is selected from carbonyl oxygen, amino acid residues Ala, Ser, Gly, Val, Leu, lle, Pro, Trp, Phe, Met Tyr, Thr, Cys, Asn, Asp, Glu, Lys, Arg, Gin, H, Orn, Sar , Hyl, Hyp, Hse or Hey, preferably Ala, Ser or Gly, - residues of the structure N- (CH 2 ) x -OH, N- (CHR9) x -CH2OH, N- (CH 2 ) x -OCOMe, where each x = 1 - 1 0, N-OH, or - residues of the structure
-■ R9 gewählt wird aus Wasserstoff und/oder Hydroxy;- ■ R9 is selected from hydrogen and / or hydroxy;
Hnhd-01938 (203-058-I)
R11 gewählt wird aus Methyl-, Hydroxymethyl-, Wasserstoff, Prop-2-yl-, Isobutyl-, But-2-yl-, Pyrrolidin-1 ,2-diyl-, 1 H-lndol-3-yl-methyl-, Benzyl-; 2-(Methylthio)ethyl-, 4- Hydroxy-benzyl-, 1 -Hydroxyethyl-, Mercaptomethyl-, 2-Amino-2-oxoethyl-, Carboxymethyl-, Carboxyethyl-, 4-Aminobutyl-, 3-{[Amino(imino)methyl]amino}propyl-, 3-Amino-3-oxopropyl-, Wasserstoff und N-Me, 3-Aminopropyl-, Ethyl-, 1 H-lmidazol-4- yl-methyl-, Butyl-, Propyl-, 4-Amino-3-hydroxy-butyl-, 4-Hydroxy-pyrrolidin-1 ,2-diyl-, Hydroxyethyl-, oder 2-Mercaptoethyl-, wobei sich mit R10 = OH dann bevorzugt die unter R4 genannten Aminosäurereste ergeben, bevorzugt ist Methyl-, Hydroxymethyl- oder Wasserstoff, , R10 gewählt wird aus Hydroxy- (-OH), - peptidisch N-verknüpfte Aminosäurereste gewählt aus Ala, Ser, Gly, Val, Leu, lle, Pro, Trp, Phe, Met Tyr, Thr, Cys, Asn, Asp, Glu, Lys, Arg, Gin, H, Orn, Sar, Hyl, Hyp, Hse oder Hey, bevorzugt ist Ala, Ser oder Gly, Resten der StrukturHnhd-01938 (203-058-I) R11 is selected from methyl, hydroxymethyl, hydrogen, prop-2-yl, isobutyl, but-2-yl, pyrrolidin-1, 2-diyl, 1 H-indol-3-yl-methyl, benzyl; 2- (methylthio) ethyl, 4-hydroxy-benzyl, 1-hydroxyethyl, mercaptomethyl, 2-amino-2-oxoethyl, carboxymethyl, carboxyethyl, 4-aminobutyl, 3 - {[amino (imino ) methyl] amino} propyl, 3-amino-3-oxopropyl, hydrogen and N-Me, 3-aminopropyl, ethyl, 1 H-imidazol-4-yl-methyl, butyl, propyl, 4 -Amino-3-hydroxy-butyl-, 4-hydroxy-pyrrolidin-1, 2-diyl-, hydroxyethyl- or 2-mercaptoethyl-, with R10 = OH then preferably giving the amino acid residues mentioned under R4, methyl is preferred -, hydroxymethyl or hydrogen,, R10 is selected from hydroxy- (-OH), - peptidically N-linked amino acid residues selected from Ala, Ser, Gly, Val, Leu, lle, Pro, Trp, Phe, Met Tyr, Thr, Cys, Asn, Asp, Glu, Lys, Arg, Gin, H, Orn, Sar, Hyl, Hyp, Hse or Hey, Ala, Ser or Gly is preferred, remnants of the structure
mit b = 1 - 6, oder with b = 1 - 6, or
- R12 gewählt wird aus Mono- bis Polysaccharide, bevorzugt einheitliche und/oder gemischte Mono-, Di- oder Trisaccharide, bevorzugt Glucose, Glycerose, Erythrose, Threose, Ribose, Arabinose, Lyxose, Xylose, Ailose, Altrose, Galactose, Gύlose, Idose, Mannose oder Talose.- R12 is selected from mono- to polysaccharides, preferably uniform and / or mixed mono-, di- or trisaccharides, preferably glucose, glycerose, erythrose, threose, ribose, arabinose, lyxose, xylose, ailose, altrose, galactose, gose, idose , Mannose or talose.
Erfindungsgemäß sind die Verbindungen 9-Retinal der StrukturformelAccording to the invention, the compounds are 9-retinal of the structural formula
Retinal Derivate der Struktur Retinal derivatives of the structure
Hnhd-01938 (203-058-1)
mit Ra und/oder Rb = Λlkyl oder gesättigte oder ungesättigte Alkoxygruppen und 9-Retinal-alkanolamin Schiffsche Base der StrukturformelHnhd-01938 (203-058-1) with Ra and / or Rb = oderlkyl or saturated or unsaturated alkoxy groups and 9-retinal-alkanolamine Schiff base of the structural formula
wobei R = R'(OH)n verzweigte oder unverzweigte Alkanole, mit R'= C1 bis C20 Kohlenwasserstoffrest und n = 1 - 5, darstellen, aus der Gruppe der erfindungsgemäßen 4-fach substituierten Cyclohexen Verbindungen ausgenommen. where R = R '(OH) n are branched or unbranched alkanols, with R' = C1 to C20 hydrocarbon radical and n = 1-5, are excluded from the group of the 4-times substituted cyclohexene compounds according to the invention.
D.h. Verbindungen der Struktur (I) mit den Resten R1 , R2, R5, R6 und R7 als Methylrest oder Alkyl, gesättigte oder ungesättigte Alkoxygruppe und R4 als Carbonylsauerstoff sowie N-R, wobei R = R'(OH)n verzweigte oder unverzweigte Alkanole, mit R'= C1 bis C20 Kohlenwasserstoffrest und n = 1 - 5, darstellen, sind nicht Inhalt der vorliegenden Erfindung.Ie compounds of structure (I) with the radicals R1, R2, R5, R6 and R7 as methyl radical or alkyl, saturated or unsaturated alkoxy group and R4 as carbonyl oxygen and NR, where R = R '(OH) n branched or unbranched alkanols, with R '= C1 to C20 hydrocarbon residue and n = 1-5, are not part of the present invention.
Bekannt ist, das Retinal (Vitamin A aldehyd) sowie deren spezifischen Derivate, wie sie beispielsweise in der US 5093360 dargelegt sind, in pharmazeutischen oder kosmetischen Zubereitungen angeboten werden, da sie einen therapeutischen Effekt ausüben. Einen Rückschluss ausgehend von diesen Verbindungen, die explizit aus der vorliegenden Erfindung ausgenommen sind, auf die erfindungsgemäßen 4-fach substituierte Cyclohexen-Verbindungen ist nicht gegeben. Es ist bekannt, dass geringfügige Änderungen in der Struktur einer chemischen Verbindung zu weitreichenden Änderungen seiner Wirkung führen können.It is known that the retinal (vitamin A aldehyde) and its specific derivatives, such as those set out in US Pat. No. 5,093,360, are offered in pharmaceutical or cosmetic preparations, since they have a therapeutic effect. A conclusion based on these compounds, which are explicitly excluded from the present invention, on the 4-fold substituted cyclohexene compounds according to the invention is not given. It is known that minor changes in the structure of a chemical compound can lead to far-reaching changes in its effects.
Überraschenderweise eignen sich die erfindungsgemäßen Substanzen, die 4-fach substituierten Cyclohexen-Verbindungen, hervorragend, um eine gesteigerte Hautbräunung herbeizuführen. Als geeignet zeigen sich alle Verbindungen der zuvor aufgeführten Strukturen, die der Fachmann, ohne erfinderisch tätig zu werden, aus den jeweiligen Gruppen auswählen kann. Selbstverständlich wird der Fachmann insbesondere für den kosmetischen oder dermatologischen AnwendungszweckSurprisingly, the substances according to the invention, the 4-times substituted cyclohexene compounds, are outstandingly suitable for bringing about increased tanning of the skin. Suitable are all compounds of the structures listed above which the person skilled in the art can select from the respective groups without being inventive. Of course, the person skilled in the art will, in particular, be used for cosmetic or dermatological purposes
Hnhd-01938 (203-058-1)
bevorzugt nur diejenigen auswählen, deren Verträglichkeit, Toxikologie oder ähnliches unkritisch, sind.Hnhd-01938 (203-058-1) Choose preferably only those whose tolerability, toxicology and the like, are not critical.
Das hauteigene Melanin hat verschiedene Funktionen, wie beispielsweise "Entgiftung'VBindung von toxischen Substanzen/Pharmaka. Darüber hinaus ist die Funktion von Melanin als natürlicher UV-Filter zum Schutz vor schädigenden UV-Strahlen sowie die Antioxidansfunktion von Melanin als Schutz vor reaktiven Sauerstoffspezies (oxidativem Stress), die unter anderem durch Sonnenstrahlung auftreten können, für die Haut sehr wichtig. Dies auch in Bezgg auf die Homöostase, Vermeidung von Hautalterung, Vermeidung von Sonnenbrand usw. Somit sollte sich nicht nur ein kosmetischer Nutzen im Sinne einer verstärkte Bräunung durch die gesteigerte Melanin- Synthese in der Haut nach topischer Applikation von erfindungsgemäß die Melanogenese steigernder Verbindungen ergeben sondern auch ein zusätzlicher Schutz durch die verschiedenen Schutzleistungen von Melanin.The skin's own melanin has various functions, such as "detoxification'V connection of toxic substances / pharmaceuticals. In addition, the function of melanin as a natural UV filter for protection against harmful UV rays and the antioxidant function of melanin as protection against reactive oxygen species (oxidative Stress), which can occur due to sun radiation, is very important for the skin, also in relation to homeostasis, avoidance of skin aging, avoidance of sunburn, etc. This should not only result in a cosmetic benefit in the sense of increased tanning due to the increased Melanin synthesis in the skin after topical application of compounds which increase the melanogenesis according to the invention also provide additional protection through the various protective functions of melanin.
Die erfindungsgemäßen Substanzen eignen sich, die physiologische Bräunung der Haut über eine gesteigerte Melaninsynthese zu verstärken und somit auch den Eigenschutz der Haut zu erhöhen. Ein wesentlicher Vorteil ist, dass diese physiologische Bräunung erreicht wird ohne sich der natürlichen Sonnenstrahlung mit ihren schädigenden Einflüssen auf die Haut aussetzen zu müssen bzw. dieses nur noch im vergleichsweise geringem Umfang nötig ist, um die gewünschte Hautbräunung zu erreichen. Neben einer zunehmenden Bräunung werden auch ungleichmäßige Pigmentierungen der Haut („uneven skin tone') ausgeglichen. Der Vorteil: das Hautbild erscheint einheitlicher, was insbesondere bei Altershaut (Altersflecken),- Melasma und postinflammatortschen Hyperpigmentierungen erwünscht ist.The substances according to the invention are suitable for strengthening the physiological tanning of the skin by means of an increased melanin synthesis and thus also increasing the skin's own protection. A major advantage is that this physiological tanning is achieved without having to be exposed to natural solar radiation with its damaging influences on the skin or that this is only necessary to a comparatively small extent in order to achieve the desired skin tanning. In addition to increasing tanning, uneven skin pigmentations ("uneven skin tone") are also compensated. The advantage: the complexion appears more uniform, which is particularly desirable for aging skin (age spots), melasma and post-inflammatory hyperpigmentation.
Gegenstand der Erfindung sind daher bevorzugt kosmetische oder dermatologische Zubereitungen enthaltend erfindungsgemäße Verbindungen, wie sie zuvor definiert sind. Gegenstand der Erfindung ist auch die Verwendung der somit hergestellten Zubereitungen. Die erfindungsgemäßen Verbindungen umfassen vereinfacht ausgedrückt ringförmige Kohlenwasserstoffverbindungen, wobei die ringförmige Struktur bevorzugt aus 6 C- Atomen aufgebaut ist und teilweise bis vollständig ungesättigt sein kann und zusätzlich mehrere, insbesondere 4, Kohlenwasserstoffsubstituenten aufweist. Bezeichnet werden die erfindungsgemäßen Verbindungen vereinfacht als 4-fach substituierte Cyclohexen- Verbindungen. Hierbei sind 3 Substituenten kurzkettig, vorzugsweise bestehend aus einer Methylgruppe (R1 , R2 und R5), ein weiterer, vierter, Substituent (R3), der auch ausThe invention therefore preferably relates to cosmetic or dermatological preparations containing compounds according to the invention, as defined above. The invention also relates to the use of the preparations thus produced. To put it simply, the compounds according to the invention comprise ring-shaped hydrocarbon compounds, the ring-shaped structure preferably being composed of 6 carbon atoms and being partially to completely unsaturated and additionally having several, in particular 4, hydrocarbon substituents. The compounds according to the invention are simply referred to as tetrasubstituted cyclohexene compounds. Here 3 substituents are short-chain, preferably consisting of a methyl group (R1, R2 and R5), a further, fourth, substituent (R3), which also consists of
Hnhd-01938 (203-058-1)
einer verzweigten und/oder teilweise bis vollständig ungesättigten Kohlenwasserstoffverbindung bestehen kann, umfasst 1 bis 25 C-Atome, bevorzugt jedoch mindestens 4 und höchstens 20 C-Atome. Das der ringförmigen Struktur gegenüberstehende Ende des „vierten Substituenten" weist bevorzugt, aber nicht zwingend ein polares Ende auf.Hnhd-01938 (203-058-1) A branched and / or partially to completely unsaturated hydrocarbon compound can comprise 1 to 25 carbon atoms, but preferably at least 4 and at most 20 carbon atoms. The end of the “fourth substituent” opposite the annular structure preferably, but not necessarily, has a polar end.
Durch intensivste Untersuchungen und P rüfungen k onnten d ie e rfindungsgemäßen 4- fach substituierten Verbindungen als geeignete Verbindungen zur Anwendung auf menschlicher Haut und Haar herauskristallisiert werden. Wesentlich dabei sind drei Grundbausteine, der Cyclohexen-Ring, die Struktur und Kettenlänge des Restes R3 sowie dessen funktionelle Gruppierungen bzw. Polaritäten. All diese Erkenntnisse führen zu den erfindungsgemäßen Verbindungen, die der Fachmann gemäß der Struktur (I) und -jeweiligen Restangaben, auswählen kann. Die erfindungsgemäßen 4-fach substituierten Cyclohexen Verbindungen sind an sich, zumindest aus synthetischer Sicht, bekannt, jedoch nicht im Zusammenhang und ihrer Eignung als Mittel zur Anwendung auf der Haut oder dem Haar erwähnt. Der Fachmann kann eine Verbindungen a us d er G ruppe d er i n A nspruch 1 a ufgeführten V erbindungen je nach Bedarf auswählen und sogar mit weiteren Verbindungen kombinieren um die erfindungsgemäß vorteilhaften Wirkungen zu erzielen. Daraus ergibt sich, dass die erfindungsgemäße Verbindung die nachfolgende allgemeine Struktur aufweist:Through intensive investigations and tests, the 4-fold substituted compounds according to the invention could be crystallized out as suitable compounds for use on human skin and hair. Three basic building blocks, the cyclohexene ring, the structure and chain length of the radical R3 and its functional groupings or polarities are essential. All of these findings lead to the compounds according to the invention, which the person skilled in the art can select according to structure (I) and any remaining information. The 4-fold substituted cyclohexene compounds according to the invention are known per se, at least from a synthetic point of view, but are not mentioned in connection with their suitability as agents for use on the skin or hair. The person skilled in the art can select a compound from the group of compounds listed in claim 1 as required and even combine it with other compounds in order to achieve the effects which are advantageous according to the invention. It follows from this that the compound according to the invention has the following general structure:
wobei R1 , R2 und R5 bevorzugt ein Methylrest ist und R3 in der zuvor beschriebenen Weise e inen C 1 -C25-Rest, b evorzugt e inen C 4-C20-Rest, d erstellt, d er b evorzugt a m entgegen gesetzten Ende eine polare Gruppe aufweist. wherein R1, R2 and R5 is preferably a methyl radical and R3 in the manner described above creates a C 1 -C 25 radical, preferably a C 4 -C 20 radical, d, which preferably forms a polar at the opposite end Group has.
Grundsätzlich ist die topische Anwendung der erfindungsgemäßen Mittel in verschiedenen, insbesondere W/O- wie auch OΛ/V-Formulierungen und anderen kosmetischen Darreichungsformen möglich und bevorzugt.In principle, the topical use of the agents according to the invention in various, in particular W / O as well as OΛ / V formulations and other cosmetic dosage forms is possible and preferred.
Von den erfindungsgemäßen Verbindungen ist Λ/-3,7-Dimethyl-9-(2,6,6- trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tretraen-1-ylidene]alanine bevorzugt, gekennzeichnet durch die Struktur .Of the compounds according to the invention, Λ / -3,7-dimethyl-9- (2,6,6-trimethylcyclohex-1-en-1-yl) nona-2,4,6,8-tretraen-1-ylidenes] is alanine preferred, characterized by the structure.
Hnhd-01938 (203-058-1)
wobei R4 über eine Iminofunktionalität gebundene Aminosäuren, insbesondere Glycin und Serin darstellen sowie R1 , R2, R5, R6 und R7 ein Methylrest ist. Beispielhaft seien hierzu folgende Synthesevorschriften zitiert: Rani, Aruna V., Tet Lett, 33, 10, 1992, 1379- 1382 und Pshenichnikova, A. B., Russ. J. Bioorg. Chem., 22, 11, 1996, 744-747 sowie Int J. Vitamin and Nutrition Research, 62, 4, 1992, 298-302 und EP 440078 A2. s.Hnhd-01938 (203-058-1) wherein R4 represent amino acids bound via an imino functionality, in particular glycine and serine, and R1, R2, R5, R6 and R7 is a methyl radical. The following synthesis instructions are cited as examples: Rani, Aruna V., Tet Lett, 33, 10, 1992, 1379-1382 and Pshenichnikova, AB, Russ. J. Bioorg. Chem., 22, 11, 1996, 744-747 and Int J. Vitamin and Nutrition Research, 62, 4, 1992, 298-302 and EP 440078 A2. s.
/V-[(2E,4E,6£,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen- 1-ylidene]-L-alanine/ V - [(2E, 4E, 6 £, 8E) -3,7-dimethyl-9- (2,6,6-trimethyl-cyclohex-1-en-1-yl) nona-2,4,6,8- tetraen-1-ylidenes] -L-alanines
mit R1,
R2, R5, R6 und R7 als Methylrest und R4 als Rest der Struktur mit R11 = Methyl und R10 als Hydroxyrest gewählt ist.with R1, R2, R5, R6 and R7 is selected as the methyl radical and R4 as the radical of the structure with R11 = methyl and R10 as the hydroxy radical.
Aus der Verbindungsstruktur (I) ergeben sich des weiteren die nachfolgend genannten bevorzugten Verbindungen (lUPAC-Namen) mit den angegeben Strukturen:From the connection structure (I), the following preferred connections (IUPAC names) with the specified structures result:
(1 E,2£,4£,6E,8.Ξ)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1 -en-1 -yl)npna-2,4,6,8-_ tetraenal oxime(1 E, 2 £, 4 £, 6E, 8.Ξ) -3,7-dimethyl-9- (2,6,6-trimethylcyclohex-1-en-1-yl) npna-2,4,6, 8-_ tetraenal oxime
mit R1, R2, R5, R6 und R7 als Methylrest und R4 als Rest der Struktur N-OH. with R1, R2, R5, R6 and R7 as the methyl radical and R4 as the radical of the structure N-OH.
- 2-{[(1£,2E,4£,6£,8iE)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8- tetraen-1-ylidene]amino}ethanol- 2 - {[(1 £, 2E, 4 £, 6 £, 8iE) -3,7-dimethyl-9- (2,6,6-trimethylcyclohex-1-en-1-yl) nona-2,4 , 6,8-tetraen-1-ylidenes] amino} ethanol
Hnhd-01938 (203-058-1)
mit R1, R2, R5, R6 und R7 als Methylrest und R4 als Rest der Struktur N-(CH2)x-OH, mit x = 2.Hnhd-01938 (203-058-1) with R1, R2, R5, R6 and R7 as the methyl radical and R4 as the radical of the structure N- (CH 2 ) x -OH, with x = 2.
- 1-{[(1£,2£,4£,6£,8£)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-. tetraen-1-ylidene]amino}propane-1 ,2,3-trioh-- 1 - {[(£ 1, £ 2, £ 4, £ 6, £ 8) -3,7-dimethyl-9- (2,6,6-trimethylcyclohex-1-en-1-yl) nona-2 , 4,6,8. tetraen-1-ylidenes] amino} propane-1, 2,3-trioh-
mit R1 , R2, R5, R6 und R7 als Methylrest und R4 als Rest der Struktur N-(CHR9)X- CH2OH, mit x = 2 und R9 = OH. with R1, R2, R5, R6 and R7 as the methyl radical and R4 as the radical of the structure N- (CHR9) X - CH2OH, with x = 2 and R9 = OH.
Λ/-[(2£,4£,6£,8£)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8- tetraen-1-ylidene]-L-alanyl-L-alanineΛ / - [(2 £, 4 £, 6 £, 8 £) -3,7-dimethyl-9- (2,6,6-trimethyl-cyclohex-1-en-1-yl) nona-2,4,6 , 8-tetraen-1-ylidenes] -L-alanyl-L-alanines
mit R4 der Struktur
, R10 mit der Struktur
1 und R11 = Methyl.with R4 of the structure , R10 with the structure 1 and R11 = methyl.
Λ/-[(2£,4£,6£,8£)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1 -en-1 -yl)nona-2,4,6,8- tetraen-1-ylidene]-L-seryl-L-serineΛ / - [(£ 2, £ 4, £ 6, £ 8) -3,7-dimethyl-9- (2,6,6-trimethylcyclohex-1-en-1-yl) nona-2,4,6 , 8-tetraen-1-ylidenes] -L-seryl-L-serines
Hnhd-01938 (203-058-1)
mit R4 der Struktur
, R10 mlt
= Hydroxymethyl.Hnhd-01938 (203-058-1) with R4 of the structure , R10 mlt = Hydroxymethyl.
Aus der Verbindungsstruktur (I) ergibt sich des weiteren die nachfolgend genannteThe connection structure (I) also gives the following
Verbindung (lUPAC-Namen) mit d en angegeben Strukturen in einer ganz besonders bevorzugten Ausführungsform:Connection (lUPAC names) with the specified structures in a very particularly preferred embodiment:
- 2-{[(1 £,2£,4£,6£,8£)-3,7-dimethyl-9-(2;6,6-trimethyicyclohex-1-en-1-yl)nona-2,4,6,8- . tetraen-1-ylidene]amino}ethyl acetat, alternativ auch als Acetyl-Retinyliminoethanol bezeichnet- 2 - {[(£ 1, £ 2, £ 4, £ 6, £ 8) -3,7-dimethyl-9- (2; 6,6-trimethyicyclohex-1-en-1-yl) nona-2 , 4,6,8-. tetraen-1-ylidene] amino} ethyl acetate, alternatively also called acetyl-retinyliminoethanol
Die Herstellungsvorschrift von Acetyl-Retinyliminoethanol lautet wie folgt:The manufacturing instructions for acetyl retinyliminoethanol are as follows:
Zu einer Lösung aus (6) (2.5g, 0.02O4 mol) in abs. Ethanol (70 ml) werden Molsieb (5g) und Retinal (7) (0.017 mol) zugefügt. Die Reaktionslösung wird bei Raumtemperatur fürTo a solution of (6) (2.5g, 0.02O4 mol) in abs. Ethanol (70 ml), molecular sieve (5 g) and retinal (7) (0.017 mol) are added. The reaction solution is at room temperature for
2 Tage gerührt. - • Stirred for 2 days. - •
Zur Aufarbeitung wird filtriert und das Lösungsmittel wird am Rotationsverdampfer entfernt.For working up, the mixture is filtered and the solvent is removed on a rotary evaporator.
Durch Säulenchromatographie (EE/MeOH 9:1 ) werden 4.4 g (8) (70%) erhalten (Smp.:91-94αC). Zusätzlich wird gegebenenfalls im Anschlύss umkristallisiert (PE/EE).Column chromatography (EA / MeOH 9: 1) gives 4.4 g (8) (70%) (m.p .: 91-94 α C). In addition, it is optionally recrystallized subsequently (PE / EE).
Diese erfindungsgemäßen Verbindungen, wobei die explizit genannten und dargestellten Verbindungen nur Beispiele für die jeweiligen Verbindungen der Struktur (I) darstellen, haben sich als Mittel zur Anwendung auf der Haut oder dem Haar bewährt. Die Verbindungen führen zu einer Steigerung der Melaninsynthese und sind bevorzugt als alleinige Zusätze bzw. als Mischung in kosmetischen oder dermatologischen Zubereitungen anzuwenden.These compounds according to the invention, the compounds explicitly mentioned and shown being only examples of the respective compounds of structure (I), have proven useful as agents for use on the skin or hair. The compounds lead to an increase in melanin synthesis and are preferably to be used as sole additives or as a mixture in cosmetic or dermatological preparations.
Hnhd-01938 (203-058-l)
Neben der Anwendung der Mittel als kosmetische oder dermatologische Zubereitung ist auch eine Polymermatrix, eine Haut- und/oder Wundauflage, ein Pflaster, ein Tuch oder Pad, ein Spray, ein Stift oder auch Textilien, beispielsweise Bandagen oder Badetextilien, um stufenlose Bräunung zu gewährleisten, als erfϊndungsgemäßes Mittel favorisiert. Vorteilhaft bei Bandagen ausgerüstet mit den erfindungsgemäßen Verbindungen ist, dass während der Tragezeit der Bandage die darunter liegende Haut eine ebensolche Braunfärbung erfährt, wie die unbedeckte Haut. \. Es hat sich durch intensives Nachforschen gezeigt, dass die erfindungsgemäßenHnhd-01938 (203-058-l) In addition to the use of the agent as a cosmetic or dermatological preparation, there is also a polymer matrix, a skin and / or wound dressing, a plaster, a cloth or pad, a spray, a pen or even textiles, for example bandages or bath textiles, in order to ensure continuous tanning , Favored as an agent according to the invention. It is advantageous in the case of bandages equipped with the compounds according to the invention that during the wearing time of the bandage, the skin underneath experiences the same brown color as the uncovered skin. \. It has been shown through intensive research that the inventive
Verbindungen in topisch anzuwendenden Mitteln, insbesondere kosmetischen oder dermatologischen Zubereitungen, zur Induktion der Pigmentierung der Haut führen. DieCompounds in topical compositions, in particular cosmetic or dermatological preparations, lead to the induction of pigmentation of the skin. The
-Melanogenese wird gesteigert, es entsteht mehr Melanin in der Haut, die Haut wird somit brauner und der Eigenschutz der H aut wird p hysiologisch e rhöht. Auch bei d er topischen Anwendung an Haaren führen die erfindungsgemäßen Verbindungen in geeigneten Zubereitungen zu einer Intensivierung der Haarfärbe, womit auch ein natürliches Ergrauen der Haare vermieden und sogar rückgängig gemacht werden kann.-Melanogenesis is increased, there is more melanin in the skin, the skin becomes brown and the skin's own protection is increased physiologically. Even when applied topically to hair, the compounds according to the invention, in suitable preparations, lead to an intensification of the hair color, with which natural graying of the hair can also be avoided and even reversed.
Die Aktivierung der hauteigenen Bräunung und die Intensivierung der Haarfärbung kann dabei selbstverständlich mit und ohne Beteiligung von UV-Licht erfolgen.The activation of the skin's own tanning and the intensification of hair coloring can of course be done with and without the involvement of UV light.
Zum Beleg der Wirksamkeit dieser Verbindungsklasse wurden jeweils Wirksamkeitstest durchgeführt. Beispielhaft sei der Test für die Verbindung 'Acetyl-Retinyliminoethanol dargestellt.Efficacy tests were carried out to prove the effectiveness of this class of compounds. The test for the compound ' acetyl-retinyliminoethanol is shown as an example.
Es wurde ein Melanogenese-Assay nach 3 Tagen Inkubation von primären normalen menschlichen Melanozyten mit Testsubstanz gegenüber Kontrolle durchgeführt. Die in der Tabelle angegebenen Zahlen geben die auf die unbehandelte Kontrolle (=100%) bezogenen Melanogeneseraten (gemessen als C14-Tyrosin-Einbau) an. Daraus ergibt sich das die Melanogenese, d.h. der Prozess der Melaninsynthese auf 253% bzw. 117% steigt, wenn die Melanozyten in Gegenwart des Acetyl-Retinyliminoethanol kultiviert werden (n=3).A melanogenesis assay was carried out after 3 days of incubation of primary normal human melanocytes with test substance versus control. The numbers given in the table indicate the melanogenesis rates based on the untreated control (= 100%) (measured as C14 tyrosine incorporation). This results in melanogenesis, i.e. the process of melanin synthesis increases to 253% and 117%, respectively, if the melanocytes are cultivated in the presence of acetyl-retinyliminoethanol (n = 3).
Hnhd-01938 (203-058-1)
Die erfindungsgemäßen Verbindungen zeichnen sich u. a. dadurch aus, dass sie - nach topischer Applikation - in der Haut die Bildung von hauteigenen Pigmenten induzieren, die Melaninsynthese steigern und auf diese Weise eine verstärkte Bräunung der Haut erzeugen, Sie sind gesundheitlich unbedenklich, nicht reizend und leicht zu handhaben, und der resultierende Farbton entspricht naturgemäß dem der natürlichen gesunden Hautfarbe. Die erhaltene Bräunung ist — d a s ie d er n atürlichen B räunung e ntspricht - lichtecht und nicht abwaschbar. Durch die erfindungsgemäßen Zubereitungen wird ferner überraschend die Bräunung bereits gebräunter Haut verstärkt und darüber hinaus das Bleichwerden gebräunter Haut verzögert. Ein weiterer Vorteil der vorliegenden Erfindung ergibt sich aus den Schutzeigensöhaften von in der Haut gebildetem natürlichem Melanin. Neben verschiedenen weiteren Funktionen des hauteigenen Melanins (wie beispielsweise "Entgiftung" bzw. Bindung von toxischen Substanzen und/oder Pharmaka etc.), sind ferner insbesondere diese Funktionen von Melanin für die Haut sehr wichtig, u. a. in Bezug auf die Homeostase, die Vermeidung der Hautalterung und dergleichen:Hnhd-01938 (203-058-1) The compounds according to the invention are distinguished, inter alia, by the fact that, after topical application, they induce the formation of the skin's own pigments in the skin, increase the melanin synthesis and in this way produce an increased tanning of the skin handle, and the resulting shade naturally corresponds to that of the natural healthy skin color. The browning obtained - which corresponds to the natural tanning - is lightfast and cannot be washed off. The preparations according to the invention also surprisingly intensify the tanning of already tanned skin and furthermore delay the bleaching of tanned skin. Another advantage of the present invention results from the protective benefits of natural melanin formed in the skin. In addition to various other functions of the skin's own melanin (such as "detoxification" or binding of toxic substances and / or pharmaceuticals etc.), these functions of melanin are also very important for the skin, in particular with regard to homeostasis, the avoidance of Skin aging and the like:
Melanin wirkt als natürlicher UV-Filter zum Schutz vor schädigenden UV-Strahlen sowie darüber hinaus als Antioxidanz zum Schutz vor reaktiven Sauerstoffspezies (oxidativem Stress), die unter anderem durch Sonnenbestrahlung auftreten können.Melanin acts as a natural UV filter to protect against damaging UV rays and also as an antioxidant to protect against reactive oxygen species (oxidative stress), which can occur, among other things, from sun exposure.
Somit ergibt sich bei erfindungsgemäßer Verwendung (d. h. nach topischer Applikation) nicht nur ein kosmetischer Nutzen im Sinne einer verstärkte Bräunung durch die gesteigerte Melanin-Synthese in der Haut sondern auch ein zusätzlicher Nutzen durch die verschiedenen Schutzleistungen von Melanin.Thus, when used according to the invention (i.e. after topical application) there is not only a cosmetic benefit in the sense of increased tanning due to the increased melanin synthesis in the skin, but also an additional benefit due to the various protective benefits of melanin.
Die erfindungsgemäßen Mittel, z.B. kosmetischen oder dermatologischen Zubereitungen, induzieren in der Haut und den Haaren die Bildung von haut- und haareigenen Pigmenten, intensivieren die vorhandene natürliche und/oder künstliche Bräunung der Haut, gleichen uneinheitliche Pigmentierung der Haut aus, intensivieren die ' natürliche Haarfärbung und lassen die Hautbräunung als auch die Haarfärbung länger anhalten.The agents according to the invention, e.g. Cosmetic or dermatological preparations induce the formation of skin and hair-specific pigments in the skin and hair, intensify the existing natural and / or artificial tanning of the skin, compensate for inconsistent pigmentation of the skin, intensify the natural hair coloring and leave the skin tanning as the hair coloring also last longer.
Die erfindungsgemäßen Formulierungen sind in jeglicher Hinsicht überaus befriedigende Präparate, die sich durch eine gleichmäßig färbende Wirkung auszeichnen. Es war für den Fachmann nicht vorauszusehen gewesen, dass die erfindungsgemäßen FormulierungenIn all respects, the formulations according to the invention are extremely satisfactory preparations which are distinguished by a uniform coloring effect. It was not foreseeable for the person skilled in the art that the formulations according to the invention
■ einfacher zu formulieren sein, ■ be easier to formulate
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■ der Haut und dem Haar schneller und besser ein natürliches Aussehen verleihen,Hnhd-01938 (203-058-1) ■ give the skin and hair a natural look faster and better,
■ die Hautbräunung und Haarfärbung länger anhalten lassen, ■ the skin tanning and hair coloring last longer,
■ besser als feuchtigkeitsspendende Zubereitungen wirken, ■ work better than moisturizing preparations,
■ besser die Hautglättung fördern, ■ sich durch bessere Pflegewirkung auszeichnen, ■ better promote smoothing of the skin, ■ are characterized by better care effects,
■ bessere sensorische Eigenschaften, wie beispielsweise die Verteilbarkeit auf der Haut und dem Haar oder das Einzugsvermögen in die Haut, aufweisen und ■ have better sensory properties, such as, for example, the spreadability on the skin and hair or the ability to be absorbed into the skin, and
■ einen besseren/risikolosen Eigenschutz der Haut und der Haare (vor UV-Strahlung) bieten würden ^ als die Zubereitungen des Standes der Technik. Zudem entfalten die erfindungsgemäßen Formulierungen überraschenderweise keine Hormonwirkungen. ■ would offer better / risk-free protection of the skin and hair (against UV radiation) than the preparations of the prior art. In addition, the formulations according to the invention surprisingly have no hormonal effects.
Der Gehalt der Verbindungen beträgt zwischen 0,0001 und 30 Gew.%, vorteilhaft zwischen 0,01 und 10 Gew.%, besonders vorteilhaft zwischen 0,02 und 2 Gew.% jeweils bezogen auf das Gesamtgewicht des Mittels.The content of the compounds is between 0.0001 and 30% by weight, advantageously between 0.01 and 10% by weight, particularly advantageously between 0.02 and 2% by weight, in each case based on the total weight of the composition.
Die erfindungsgemäßen kosmetischen und/oder dermatologischen Formulierungen können wie üblich zusammengesetzt sein und insbesondere zur Behandlung und der Pflege der Haut und/oder der Haare, als Schminkprodukt in der dekorativen Kosmetik oder als Lichtschutz- bzw. sogenanntes Pre- oder Aftersunpräparat dienen. Entsprechend können die erfindungsgemäßen Formulierungen - je nach ihrem Aufbau - beispielsweise verwendet werden als Hautschutzcreme, Gesichtscreme, Reinigungsmilch, Sonnenschutzlotion, Nährcreme, Tages- oder Nachtcreme usw.The cosmetic and / or dermatological formulations according to the invention can be composed as usual and can be used in particular for the treatment and care of the skin and / or hair, as a make-up product in decorative cosmetics or as a sunscreen or so-called pre or after preparation. Correspondingly, depending on their structure, the formulations according to the invention can be used, for example, as skin protection cream, face cream, cleansing milk, sunscreen lotion, nutrient cream, day or night cream, etc.
Es ist auch möglich und vorteilhaft im Sinne der vorliegenden Erfindung, die erfindungsgemäßen Verbindungen in wässrige Systeme bzw. Tensidzubereitungen zur Reinigung und Pflege der Haut und der Haare einzufügen. Dies umfasst sowohl Duschgels, Shampoos aber auch Conditioner, Haarpflegekuren, Haarspülungen, Haartonics, Sprays etc. ' . ' It is also possible and advantageous for the purposes of the present invention to insert the compounds according to the invention into aqueous systems or surfactant preparations for cleaning and care of the skin and hair. This includes shower gels, shampoos as well as conditioners, hair care treatments, hair rinses, hair tonics, sprays etc. ' . '
Es ist dem Fachmann natürlich bekannt, dass anspruchsvolle kosmetische Zusammensetzungen zumeist n icht ohne die üblichen Hilfs- und Zusatzstoffe denkbar sind. Darunter zählen beispielsweise Konsistenzgeber, Füllstoffe, Parfüm, Farbstoffe, Emul- gatoren, zusätzliche Wirkstoffe wie Vitamine oder Proteine, Lichtschutzmittel, Sta- bilisatoren, Insektenrepellentien, Alkohol, Wasser, Salze, antimikrobiell, proteolytisch oder keratolytisch wirksame Substanzen usw.It is of course known to the person skilled in the art that sophisticated cosmetic compositions are usually inconceivable without the customary auxiliaries and additives. These include, for example, consistency enhancers, fillers, perfumes, dyes, emulsifiers, additional active ingredients such as vitamins or proteins, light stabilizers, stabilizers, insect repellents, alcohol, water, salts, antimicrobial, proteolytic or keratolytically active substances, etc.
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Es ist auch vorteilhaft, den oder die erfindungsgemäßen Verbindungen in verkapselter Form darzureichen, z.B. in Kollagenmatrices und anderen üblichen Verkapselungsmaterialien, wie z.B. cyclische Oligosaccharide (insbesondere alpha, beta-, HP-beta-, random-Me-beta, gamma-Cyclodextrin), wobei entsprechend der dem Fachmann bekannten chemischen Eigenschaften der erfindungsgemässen Verbindungen alpha-, beta- oder gamma- Cyclodextrine als Verkapselungsmatrial verwendet werden. Ferner kann es von Vorteil sein, die erfindungsgemässen Verbindungen oder deren Mischungen in Form von Celluloseverkapselungen, in Gelatine, Wachsmatrices oder liposomal verkapselt darzureichen. Bei der Verkapselung mit Cyclodextrinen nimmt man an, dass die Cyclodextringerüste dabei als Wirtsmolekül und der erfindungsgemäße Wirkstoff als Gastmolekül fungieren. Zur Herstelllung werden Cyclodextrine in Wasser gelöst und erfindungsgemäßer Wirkstoff hinzugegeben. Das molekulare Addukt fällt sodann als Festkörper aus und kann den üblichen Reinigungs- und Aufbereitungsschritten unterworfen werden. Es ist bekannt, dass Cyclodextrin-Gast-Kornplexe in einem entsprechenden Lösungsmittel (z.B. Wasser) in einem Gleichgewicht stehen zwischen dem konkreten Gast- Cyclodextrin Komplex und der dissoziierten Form, wobei Cyclodextrin und Gast zu einem gewissen Anteil separiert sein können. Solche Gleichgewichtssysteme sind ebenfalls vorteilhaft im Sinne der vorliegenden Erfindung.Hnhd-01938 (203-058-1) It is also advantageous to present the compound or compounds according to the invention in encapsulated form, for example in collagen matrices and other customary encapsulation materials, such as, for example, cyclic oligosaccharides (in particular alpha, beta, HP-beta, random-Me-beta, gamma-cyclodextrin), where, according to the chemical properties known to the person skilled in the art, alpha-, beta- or gamma-cyclodextrins are used as encapsulation material. Furthermore, it may be advantageous to present the compounds according to the invention or their mixtures in the form of cellulose encapsulations, encapsulated in gelatin, wax matrices or liposomally. When encapsulated with cyclodextrins, it is assumed that the cyclodextrin skeletons act as the host molecule and the active ingredient according to the invention acts as the guest molecule. For the preparation, cyclodextrins are dissolved in water and the active ingredient according to the invention is added. The molecular adduct then precipitates as a solid and can be subjected to the usual cleaning and preparation steps. It is known that cyclodextrin-guest complexes in an appropriate solvent (eg water) are in equilibrium between the specific guest-cyclodextrin complex and the dissociated form, it being possible for cyclodextrin and guest to be separated to a certain extent. Such balance systems are also advantageous in the sense of the present invention.
Mutatis mutandis gelten entsprechende Anforderungen an die Formulierung medizinischer Zubereitungen.Mutatis mutandis, corresponding requirements apply to the formulation of medical preparations.
Medizinische topische Zusammensetzungen im Sinne der vorliegenden Erfindung ent- halten in der Regel ein oder mehrere Medikamente in wirksamer Konzentration. Der Einfachheit halber wird zur sauberen Unterscheidung zwischen kosmetischer und medizinischer Anwendung und entsprechenden Produkten auf die gesetzlichen Bestimmungen der Bundesrepublik Deutschland verwiesen (z.B. Kosmetikverordnung, Lebensmittel- und Arzneimittelgesetz). Es ist dabei ebenfalls von Vorteil, die erfindungsgemäße Verbindung(en) als Zusatzstoff zu Zubereitungen zu geben, die bereits andere Wirkstoffe für andere Zwecke enthalten. So zeigte es sich bei der vorliegenden Erfindung überraschenderweise, dass die erfindungsgemäßen Formulierungen sich auch ganz besonders eignen für Kombinationen mit Wirkstoffen, die den Zustand der Haut positiv beeinflussen. So zeigte sich, dass Wirkstoffe zur positiven Beeinflussung der Altershaut, die die Entstehung von Falten oder auch bestehenden Falten vermindern. So insbesondere inMedical topical compositions in the sense of the present invention generally contain one or more drugs in effective concentration. For the sake of simplicity, reference is made to the legal provisions of the Federal Republic of Germany (e.g. cosmetics regulation, food and drug law) for a clear distinction between cosmetic and medical use and corresponding products. It is also advantageous to add the compound (s) according to the invention as an additive to preparations which already contain other active ingredients for other purposes. It was surprisingly found in the present invention that the formulations according to the invention are also particularly suitable for combinations with active ingredients which have a positive effect on the condition of the skin. It has been shown that active ingredients to positively influence the aging skin, which reduce the appearance of wrinkles or existing wrinkles. So especially in
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Kombination mit Biochinone, insbesondere Ubichinon Q10, Kreatin, Kreatinin, Camitin, Biotin, Isoflavon, Cardiolipin, Liponsäure, Anti Freezing Proteine, Hopfen- und Hopfen- Malz-Extrakte. Auch fördernde Mittel der Restrukturierung des Bindegewebes, wie Isoflavonoide sowie Isoflavonoid-haltige Pfla nzenextrakte wie z.B. Soja- und Klee- Extrakte können in den erfindungsgemäßen Formulierungen sehr gut verwendet werden. Auch zeigt sich, dass sich die Formulierungen in besonderer Weise eignen, Wirkstoffe zur Unterstützung der Hautfunktionen bei trockener Haut, wie beispielsweise Vitamin C, Biotin, Camitin, Kreatin, Propionsäure, Grüntee-Extrakte, Eucalyptusöl, Harnstoff und Mineralsalze wie z. B. NaCI, Meeresmineralien sowie Osmolyte wie z. B. Taurin, Inositol, Betain, quartäre Ammoniumverbindungen, zu verwenden. In ähnlicher Weise erwies sich die Einarbeitung von Wirkstoffen zur Linderung bzw. positiven Beeinflussung von irritativen Hautzuständen, sei es bei empfindlicher Haut im allgemeinen oder bei durch Noxen gereizter Haut (UV-Licht, . Chemikalien), als vorteilhaft. Hier sind Wirkstoffe , zu nennen wie Sericoside, verschiedene Extrakte d es S üssholzes, Licochalcone, insbesondere Licochalocon A, Silymarin, Silyphos, Dexpanthenol, Inhibitoren des Prostaglandinstoffwechsels, insbesondere der Cyclooxygenase und des Leukotrienstoffwechsels, insbesondere der 5-Lipoxyaenase, aber auch des 5-Lipoxvgenase Inhibitor Proteins, FLAP. Auch erwies sich die Einarbeitung von Modulatoren der Pigmentierung als vorteilhaft. Hier sind Wirkstoffe zu nennen, die die Pigmentierung der Haut vermindern und so zu einer kosmetisch gewünschten Aufhellung der Ha ut führen und/oder das Auftreten von Altersflecken reduzieren und/oder bestehende Altersflecken aufhellen. Beispielhaft sei erwähnt Tyrosinsulfat, Dioic acid (8-Hexadecen-1 ,16-dicarbonsäure sowie Liponsäure und Liponamid, verschiedene Extrakte des Süssholzes. Kojisäure, HydroGhinon, - Arbutin, Fruchtsäuren, insbesondere Alpha-Hydroxy-Säuren (AHAs), Bearberry (Uvae ursi), Ursolsäure, Ascorbinsäure. Grüntee-Extrakte, Aminoguanidin, Pyridoxamin. In gleicher Weise erwiesen sich die erfindungsgemäßen Formulierungen als hervorragende Kombinationspartner für weitere Wirkstoffe, die eine verstärkte oder schnellere Bräunung der Haut herbeiführen (Advanced Glycation Endproducts (AGE), Lipofuscine, NukleinsäureOligonukleotide, Purine und Pyrimidine, NO-freisetzende Substanzen), sei es mit oder ohne Einfluss von UV-Licht.Hnhd-01938 (203-058-1) Combination with bioquinones, especially ubiquinone Q10, creatine, creatinine, camitin, biotin, isoflavone, cardiolipin, lipoic acid, anti freezing proteins, hop and hop malt extracts. Promotional agents for the restructuring of the connective tissue, such as isoflavonoids and isoflavonoid-containing plant extracts such as, for example, soybean and clover extracts, can also be used very well in the formulations according to the invention. It also shows that the formulations are particularly suitable, active ingredients to support skin functions in dry skin, such as vitamin C, biotin, camitin, creatine, propionic acid, green tea extracts, eucalyptus oil, urea and mineral salts such as. B. NaCI, marine minerals and osmolytes such. B. taurine, inositol, betaine, quaternary ammonium compounds to use. In a similar way, the incorporation of active ingredients to alleviate or positively influence irritative skin conditions, be it with sensitive skin in general or with skin irritated by noxious substances (UV light,. Chemicals), was advantageous. Active substances, such as sericosides, various extracts of liquorice, licochalcones, in particular licochalocon A, silymarin, silyphos, dexpanthenol, inhibitors of prostaglandin metabolism, in particular cyclooxygenase and leukotriene metabolism, in particular 5-lipoxyenase, but also 5- Lipoxvase inhibitor protein, FLAP. The incorporation of pigmentation modulators also proved to be advantageous. Active substances are to be mentioned here which reduce the pigmentation of the skin and thus lead to a cosmetically desired lightening of the skin and / or reduce the appearance of age spots and / or lighten existing age spots. Examples include tyrosine sulfate, dioic acid (8-hexadecen-1, 16-dicarboxylic acid as well as lipoic acid and liponamide, various extracts of licorice. Kojic acid, HydroGhinon, arbutin, fruit acids, especially alpha-hydroxy acids (AHAs), bearberry (Uvae ursi ), Ursolic acid, ascorbic acid, green tea extracts, aminoguanidine, pyridoxamine. In the same way, the formulations according to the invention proved to be excellent combination partners for other active ingredients which bring about enhanced or faster tanning of the skin (advanced glycation end products (AGE), lipofuscins, nucleic acid oligonucleotides, Purines and pyrimidines, NO-releasing substances), be it with or without the influence of UV light.
Besonders bevorzugt sind solche kosmetischen und dermatologischen Zubereitungen, die in der Form eines Sonnenschutzmittels vorliegen. Vorteilhaft können diese zusätzlich mindestens einen weiteren UVA-Filter und/oder mindestens einen weiteren UVB-FilterCosmetic and dermatological preparations in the form of a sunscreen are particularly preferred. These can advantageously also have at least one further UVA filter and / or at least one further UVB filter
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und/oder mindestens ein anorganisches Pigment, bevorzugt ein anorganisches Mikropigment, enthalten.Hnhd-01938 (203-058-1) and / or contain at least one inorganic pigment, preferably an inorganic micropigment.
Erstaunlicherweise sind kosmetische und dermatologische Zubereitungen gemäß der Erfindung imstande, eine zeitliche Verlängerung der natürlichen Bräunung herbeizuführen.Surprisingly, cosmetic and dermatological preparations according to the invention are able to prolong the natural tanning process.
Weiterhin war erstaunlich, dass kosmetische und dermatologische Formulierungen gemäß der Erfindung imstande sind, zur Behandlung von Hypopigmentierungen (Vitiligo, ungleichmäßige Pigmentierung in Altershaut usw.) zu dienen.It was also astonishing that cosmetic and dermatological formulations according to the invention are able to serve for the treatment of hypopigmentation (vitiligo, uneven pigmentation in aging skin, etc.).
. Die kosmetischen und dermatologischen Zubereitungen können erfindungsgemäß kosmetische Hilfsstoffe enthalten, wie sie üblicherweise in solchen Zubereitungen verwendet werden, z.B. Konservierungsmittel, Bakterizide, Parfüme, Substanzen zum Verhindern des Schäumens, Farbstoffe, Pigmente, die eine färbende Wirkung haben, Verdickungsmittel, anfeuchtende und/oder feuchthaltende Substanzen, Fette, Öle, Wachse oder andere übliche Bestandteile einer kosmetischen oder dermatologischen Formulierung wie Alkohole, Polyole, Polymere, Schaumstabilisatoren, Elektrolyte, organische Lösungsmittel, Silikonderivate oder Moisturizer., According to the invention, the cosmetic and dermatological preparations can contain cosmetic auxiliaries as are usually used in such preparations, e.g. Preservatives, bactericides, perfumes, substances to prevent foaming, dyes, pigments that have a coloring effect, thickeners, moisturizing and / or moisturizing substances, fats, oils, waxes or other common components of a cosmetic or dermatological formulation such as alcohols, polyols, Polymers, foam stabilizers, electrolytes, organic solvents, silicone derivatives or moisturizers.
Als Moisturizer werden Stoffe oder Stoffgemische bezeichnet, welche kosmetischen oder dermatologischen Zubereitungen die Eigenschaft verleihen, n ach d em A uftragen bzw. Verteilen, auf der Hautoberfläche die Feuchtigkeitsabgabe der Homschicht (auchMoisturizers are substances or mixtures of substances that give cosmetic or dermatological preparations the property that after application or distribution, the release of moisture from the skin layer on the skin surface (also
' .transepidermal. water loss (TEWL) genannt) zu reduzieren und/oder die Hydratation der Homschicht positiv zu beeinflussen. ' . transepidermally. to reduce water loss (called TEWL)) and / or to positively influence the hydration of the homolayer.
Vorteilhafte Moisturizer im Sinne der vorliegenden Erfindung sind beispielsweise Glyce- rin, Milchsäure, Pyrrolidoncarbonsäure und Harnstoff. Ferner ist es insbesondere von Vorteil, polymere Moisturizer aus der Gruppe der wasserlöslichen und/oder in Wasser qüellbaren und/oder mit Hilfe von Wasser gelierbaren Polysaccharide zu verwenden. Insbesondere vorteilhaft sind beispielsweise Hyaluronsäure und/oder ein fucosereiches Polysaccharid, welches in den Chemical Abstracts unter der Registraturnummer 178463-23-5 abgelegt und z. B. unter der Bezeichnung Fucogel®1000 von der Gesellschaft SOLABIA S.A. erhältlich ist.Advantageous moisturizers for the purposes of the present invention are, for example, glycerin, lactic acid, pyrrolidone carboxylic acid and urea. Furthermore, it is particularly advantageous to use polymeric moisturizers from the group of water-soluble and / or water-swellable and / or water-gelable polysaccharides. Particularly advantageous are, for example, hyaluronic acid and / or a fucose-rich polysaccharide, which is filed in the Chemical Abstracts under the registration number 178463-23-5 and z. B. under the name Fucogel®1000 from the company SOLABIA S.A. is available.
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Glycerin kann als Moisturizer im Sinne der vorliegenden Anmeldung im Bereich von 0,05-30 Gew.%, besonders bevorzugt sind 1-10%, eingesetzt werden.Hnhd-01938 (203-058-1) Glycerin can be used as a moisturizer in the sense of the present application in the range of 0.05-30% by weight, particularly preferably 1-10%.
Die jeweils einzusetzenden Mengen an kosmetischen oder dermatologischen Hilfs- und Trägerstoffen und Parfüm können in Abhängigkeit von der Art des jeweiligen Produktes vom Fachmann durch einfaches Ausprobieren leicht ermittelt werden.The respective amounts of cosmetic or dermatological auxiliaries and carriers and perfume can be easily determined by a person skilled in the art, depending on the type of product, by simply trying them out.
Ein zusätzlicher Gehalt an Antioxidantien in den erfindungsgemäßen Zubereitungen ist im allgemeinen bevorzugt. Erfindungsgem^ß können als günstige Antioxidantien alle für kosmetische und/oder dermatologische Anwendungen geeigneten oder gebräuchlichen Antioxidantien verwendet werden.An additional content of antioxidants in the preparations according to the invention is generally preferred. According to the invention, all the antioxidants suitable or customary for cosmetic and / or dermatological applications can be used as favorable antioxidants.
Es ist daher von Vorteil, den erfindungsgemäßen Zubereitungen Antioxidantien zuzusetzen. Vorteilhaft werden die Antioxidantien gewählt aus der Gruppe bestehend aus Aminosäuren (z.B. Glycin, Histidin, Tyrosin, Phenylalanin, Tryptophan) und deren Derivate (insbesondere N-Acetyl-Tyrosin, N-Acetyl-Phenylalanin), Imidazole (z.B. Uroca- ninsäure) und deren Derivate, Peptide wie D.L-Camosin, D-Camosin, L-Camosin und deren Derivate (z.B. Anserin), Carotinoide, Carotine (z.B. -Carotin, §-Carotin, Lycopin) und deren Derivate, Chlorogensäure und deren Derivate, Liponsäure und deren Derivate (z.B. Dihydroliponsäure), Aurothioglucose, Propylthiouracil und andere Thiole (z.B. Thioredoxin, Glutathion, Cystein, Cystin, Cystarmin und deren Glycosyl-, N-Acetyl-, Methyl-, Ethyl-, Propyl-, Amyl-, Butyl- und Lauryl-, Palmitoyl-, Oleyl-, -Linoleyl-, Cholesteryl- und Glycerylester) sowie deren Salze, Dilaurylthlodipropionat, Distearylthio- dipropionat, Thiodipropionsäure und deren Derivate (Ester, Ether, Peptide, Lipide, Nukleotide, Nukleoside und Salze) sowie Sulfoximinverbindungen (z.Br^Buthronin- sulfoximine, Homocysteinsulfoximin, Buthioninsulfoπe, Penta-, Hexa-, Heptathio- ninsulfoximin) in sehr geringen verträglichen Dosierungen (z.B. pmol bis μmol/kg), ferner (Metall)-Chelatoren (z.B. α-Hydroxyfettsäuren, Palmitinsäure, Phytinsäure, Lactoferrin), α -Hydroxysäuren (z.B. Citronensäure, Milchsäure, Apfelsäure), Huminsäure, Gallensäure, Gallenextrakte, Bilirubin, Biliverdin, EDTA, EGTA und deren Derivate, ungesättigte Fett- säuren und deren Derivate (z.B. γ-Linolensäure, Linolsäure, Ölsäure), Folsäure und deren Derivate, Ubichinon und Ubichinol und deren Derivate, Vitamin C und Derivate (z.B. Ascorbylpalmitat, Mg-Ascorbylphosphat, Ascorbylacetat), Tocopherole und Derivate (z.B. Vitamin-E-acetat), Vitamin A und Derivate (Vitamin-A-palmitat) sowie- Koniferyl- benzoat des Benzoeharzes, Rutinsäure und deren ' Derivate, α-Glycosylrütin, Ferulasäure, Furfurylidenglucitol, Carnosin, Butylhydroxytoluol, Butylhydroxyanisol,It is therefore advantageous to add antioxidants to the preparations according to the invention. The antioxidants are advantageously selected from the group consisting of amino acids (for example glycine, histidine, tyrosine, phenylalanine, tryptophan) and their derivatives (in particular N-acetyl-tyrosine, N-acetyl-phenylalanine), imidazoles (for example urocanic acid) and their Derivatives, peptides such as DL-camosin, D-camosin, L-camosin and their derivatives (e.g. anserine), carotenoids, carotenes (e.g. -carotene, §-carotene, lycopene) and their derivatives, chlorogenic acid and its derivatives, lipoic acid and its derivatives (e.g. dihydroliponic acid), aurothioglucose, propylthiouracil and other thiols (e.g. thioredoxin, glutathione, cysteine, cystine, cystarmine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, Palmitoyl, oleyl, linoleyl, cholesteryl and glyceryl esters) and their salts, dilaurylthlodipropionate, distearylthio dipropionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) and sulfoximine compounds (e.g. ^ Buthronine - sulfoximines, homocysteine sulfoximine, buthionine sulfones, penta-, hexa-, heptathione sulfoximine) in very low tolerable doses (e.g. pmol to μmol / kg), also (metal) chelators (e.g. α-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), α-Hydroxy acids (eg citric acid, lactic acid, malic acid), humic acid, bile acid, bile extracts, bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives (eg γ-linolenic acid, linoleic acid, oleic acid), folic acid and their Derivatives, ubiquinone and ubiquinol and their derivatives, vitamin C and derivatives (e.g. ascorbyl palmitate, Mg ascorbyl phosphate, ascorbyl acetate), tocopherols and derivatives (e.g. vitamin E acetate), vitamin A and derivatives (vitamin A palmitate) and coniferyl - benzoate of benzoin, rutinic acid and their 'derivatives, α-Glycosylrütin, ferulic acid, Furfurylidenglucitol, carnosine, butylhydroxytoluene, butylhydroxyanisole,
Hnhd-01938 (203-058-1)
Nordihydroguajakharzsäure, Nordihydroguajaretsäure, Trihydroxybutyrophenon, Harnsäure und deren Derivate, Mannose und deren Derivate, Zink und dessen Derivate (z.B. ZnO, ZnS0 ) Selen und dessen Derivate (z.B. Selenmethionin), Stilbene und deren Derivate (z.B. Stilbenoxid, Trans-Stilbenoxid) und die erfindungsgemäß geeigneten Derivate (Salze, Ester, Ether, Zucker, Nukleotide, Nukleoside, Peptide und Lipide) dieser genannten Wirkstoffe.Hnhd-01938 (203-058-1) Nordihydroguajakarzarzäure, Nordihydroguajaretsäure, trihydroxybutyrophenon, uric acid and its derivatives, mannose and its derivatives, zinc and its derivatives (e.g. ZnO, ZnS0) selenium and its derivatives (e.g. selenomethionine), stilbene and their derivatives (e.g. stilbene oxide, trans-stilbene oxide) suitable derivatives (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids) of these active ingredients.
Die Menge der vorgenannten Antioxidantien (eine oder mehrere Verbindungen) in den Zubereitungen beträgt vorzugsweise 0,001 bis 30 Gew.-%, besonders bevorzugt 0,05 - 20 Gew.-%, insbesondere 1 - 10 Gew.-%, bezogen auf das Gesamtgewicht der Zubereitung.The amount of the aforementioned antioxidants (one or more compounds) in the preparations is preferably 0.001 to 30% by weight, particularly preferably 0.05-20% by weight, in particular 1-10% by weight, based on the total weight of the Preparation.
Sofern Vitamin E und/oder dessen Derivate das oder die Antioxidantien d anstellen, I st vorteilhaft, deren jeweilige Konzentrationen aus dem Bereich von 0,001 - 10 Gew.%, be- zogen auf das Gesamtgewicht der Formulierung, zu wählen. Sofern Vitamin A, bzw. Vitamin-A-Derivate, bzw. Carotine bzw. deren Derivate das oder die Antioxidantien darstellen, ist vorteilhaft, deren jeweilige Konzentrationen aus dem Bereich von 0,001 - 10 Gew.-%, bezogen auf das Gesamtgewicht der Formulierung, zu wählen.If vitamin E and / or its derivatives turn on the antioxidant (s) d, it is advantageous to choose their respective concentrations from the range from 0.001 to 10% by weight, based on the total weight of the formulation. If vitamin A or vitamin A derivatives or carotenes or their derivatives represent the antioxidant or antioxidants, it is advantageous to use their respective concentrations in the range from 0.001-10% by weight, based on the total weight of the formulation, to choose.
Kosmetische oder dermatologische Formulierungen im Sinne der vorliegenden Erfindung können bevorzugt neben einer oder mehrerer Ölphasen zusätzlich eine oder mehrere Wasserphasen enthalten und beispielsweise in Form von W/O-, O/W-, W/O/W- oder OΛ/V/O-Emulsionen vorliegen. Solche Emulsionen können vorzugsweise auch eine -Mikroemulsion, eine- Pickering-Emulsion-odef eine sprühbare Emulsion sein. -Cosmetic or dermatological formulations in the sense of the present invention can preferably contain, in addition to one or more oil phases, one or more water phases and, for example, in the form of W / O-, O / W-, W / O / W- or OΛ / V / O- Emulsions are present. Such emulsions can preferably also be a microemulsion, a Pickering emulsion or a sprayable emulsion. -
Darüber hinaus können die erfindungsgemäßen Formulierungen aber auch vorteilhaft in Form von ölfreien Zubereitungen, wie beispielsweise Gelen, oder als wasserfreie Zubereitungen vorliegen.In addition, the formulations according to the invention can also advantageously be in the form of oil-free preparations, such as gels, or as anhydrous preparations.
Die erfindungsgemäßen Formulierungen können ferner vorteilhaft auch Dihydroxyaceton oder Nußextrakte enthalten sowie weitere Substanzen, welche die Bräune erhalten oder erzeugen oder zusätzlich verstärken sollen.The formulations according to the invention can furthermore advantageously also contain dihydroxyacetone or nut extracts as well as other substances which are intended to maintain or produce the tan or to additionally reinforce them.
Die Lipidphase der erfindungsgemäßen Emulsionen kann vorteilhaft gewählt werden aus folgender Substanzgruppe: Mineralöle, MineralwachseThe lipid phase of the emulsions according to the invention can advantageously be selected from the following group of substances: mineral oils, mineral waxes
Hnhd-01938 (203-058-1)
Öle, wie Triglyceride der Caprin- oder der Caprylsäure, vorzugsweise aber Rizinusöl; Fette, Wachse und andere natürliche und synthetische Fettkörper, vorzugsweise Ester von Fettsäuren mit Alkoholen niedriger C-Zahl, z.B. mit Isopropanol, Propy- lenglykol oder Glycerin, oder Ester von Fettalkoholen mit Alkansäuren niedriger C-Zahl oder mit Fettsäuren; Alkylbenzoate; Silikonöle wie Dimethylpolysiloxane, Diethylpolysiloxane, Diphenylpolysiloxane sowie Mischformen daraus.Hnhd-01938 (203-058-1) Oils, such as triglycerides of capric or caprylic acid, but preferably castor oil; Fats, waxes and other natural and synthetic fat bodies, preferably esters of fatty acids with alcohols with a low C number, for example with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids with a low C number or with fatty acids; benzoates; Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and mixed forms thereof.
Die ö lphase d er E mulsionen, O leogele b zw. Hydrodispersionen oder Lipodispersionen im Sinne der vorliegenden Erfindung wird vorteilhaft gewählt aus der Gruppe der Ester aus gesättigten und/oder ungesättigten, verzweigten und/oder unverzweigten Alkancar- bonsäuren einer Kettenlänge von 3 bis 30 C-Atomen und gesättigten und/oder ungesät- tigten, verzweigten und/oder unverzweigten Alkoholen einer Kettenlänge von 3 bis 30 C- Atomen, aus der Gruppe der Ester aus aromatischen Carbonsäuren und gesättigten und/oder ungesättigten, verzweigten und/oder unverzweigten Alkoholen einer Kettenlänge von 3 bis 30 C-Atomen. Solche Esteröle können dann vorteilhaft gewählt werden aus. der Gruppe Isopropylmyristat, Isopropylpalmitat, Isopropylstearat, Isopropyl- oleat, n-Butylstearat, n-Hexyllaurat, n-Decyloleat, Isooctylstearat, Isononylstearat, Iso- nonylisononanoat, 2-Ethylhexylpalmitat, 2-Ethylhexyllaurat, 2-Hexyldecylstearat, 2-Oc- tyldodecylpalmitat, Oleyloleat, Oleylerucat, Erucyloleat, Erucylerucat sowie synthetische, halbsynthetische und natürliche Gemische solcher Ester, z.B. Jojobaöl.The oil phase of the emulsions, oligogels or hydrodispersions or lipodispersions within the meaning of the present invention is advantageously selected from the group of esters from saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 3 to 30 C atoms and saturated and / or unsaturated, branched and / or unbranched alcohols with a chain length of 3 to 30 C atoms, from the group of esters from aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols Chain length from 3 to 30 carbon atoms. Such ester oils can then advantageously be selected from. the group isopropyl myristate, isopropyl palmitate, isopropyl stearate, isopropyl oleate, n-butyl stearate, n-hexyl laurate, n-decyl oleate, isooctyl stearate, isononyl stearate, isononyl isononanoate, 2-ethylhexyl palmitate, 2-ethylhexyldlate, 2-ethylhexyldlate, Oleyl oleate, Oleylerucat, Erucyloleat, Erucylerucat as well as synthetic, semi-synthetic and natural mixtures of such esters, for example Jojoba oil.
Ferner kann die ölphase vorteilhaft gewählt werden aus der Gruppe der verzweigten und unverzweigten Kohlenwasserstoffe und -wachse, der Silikonöle, der Dialkylether, der Gruppe der gesättigten oder ungesättigten, verzweigten oder unverzweigten Alkohole, sowie der Fettsäuretriglyceride, namentlich der Triglycerinester gesättigter und/oder ungesättigter, verzweigter und/oder unverzweigter Alkancarbonsäuren einer Kettenlänge von 8 bis 24, insbesondere 12 - 18 C-Atomen. Die Fettsäuretriglyceride können beispielsweise vorteilhaft, gewählt werden aus der Gruppe der synthetischen, halbsynthetischen und natürlichen Öle, z.B. Olivenöl, Sonnenblumenöl, Sojaöl, Erdnußöl, Rapsöl, Mandelöl, Palmöl, Kokosöl, Palmkemöl und dergleichen mehr.The oil phase can also advantageously be selected from the group of branched and unbranched hydrocarbons and waxes, silicone oils, dialkyl ethers, the group of saturated or unsaturated, branched or unbranched alcohols, and also fatty acid triglycerides, especially the triglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkane carboxylic acids with a chain length of 8 to 24, in particular 12 - 18 carbon atoms. The fatty acid triglycerides can for example advantageously be selected from the group of synthetic, semi-synthetic and natural oils, e.g. Olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, coconut oil, palm kernel oil and the like.
Auch beliebige Abmischungen solcher öl- und Wachskomponenten sind vorteilhaft i m Sinne der vorliegenden Erfindung einzusetzen. Es kann auch gegebenenfalls vorteilhaftAny mixtures of such oil and wax components can also be used advantageously for the purposes of the present invention. It can also be advantageous if necessary
Hnhd-01'938 (203-058-I)
sein, Wachse, beispielsweise Cetylpalmitat, als alleinige Lipidkomponente der ölphase einzusetzen. • Hnhd-01 ' 938 (203-058-I) be waxes, for example cetyl palmitate, to be used as the sole lipid component of the oil phase. •
Vorteilhaft wird die ölphase gewählt aus der Gruppe 2-Ethylhexylisostearat, Octyldode- canol, Isotridecylisononanoat, Isoeicosan, 2-Ethylhexylcocoat, C12-15-Alkylbenzoat, Capryl-Caprinsäure-triglycerid, Dicaprylylether.The oil phase is advantageously selected from the group 2-ethylhexyl isostearate, octyldodecanol, isotridecyl isononanoate, isoeicosane, 2-ethylhexyl cocoate, C 12-15 alkyl benzoate, caprylic capric acid triglyceride, dicaprylyl ether.
Besonders vorteilhaft sind Mischungen aus d2.15-Alkylbenzoat und 2-Ethylhexylisostea- rat, Mischungen aus C12-ι5-Alkylbenzoat und Isotridecylisononanoat sowie Mischungen aus Ci2-i5-Alkylbenzoat, 2-Ethylhexylisostearat und Isotridecylisononanoat.Mixtures of d 2 are particularly advantageous. C15 alkyl benzoate and 2-ethylhexyl isostearate, mixtures of C 12- ι 5 alkyl benzoate and isotridecyl isononanoate and mixtures of Ci2-i5-alkyl benzoate, 2-ethylhexyl isostearate and isotridecyl isononanoate.
Von den Kohlenwasserstoffen sind Paraffinöl, Squalan und Squalen vorteilhaft im Sinne der vorliegenden Erfindung zu verwenden.Of the hydrocarbons, paraffin oil, squalane and squalene can be used advantageously for the purposes of the present invention.
Vorteilhaft kann die ölphase ferner einen Gehalt an cyclischen oder linearen Silikonölen aufweisen oder vollständig aus solchen ölen bestehen, wobei allerdings bevorzugt wird, außer dem Silikonöl oder den Silikonölen einen zusätzlichen Gehalt an anderen ölpha- senkomponenten zu verwenden.The oil phase can advantageously also have a content of cyclic or linear silicone oils or consist entirely of such oils, although it is preferred to use an additional content of other oil phase components in addition to the silicone oil or the silicone oils.
Vorteilhaft wird Cyclomethicon (Oetamethyleyclotetrasiloxan) als erfindungsgemäß zu verwendendes Silikonöl eingesetzt. Aber auch andere Silikonöle sind vorteilhaft im Sinne der vorliegenden Erfindung zu verwenden, beispielsweise Hexamethylcyclotrisiloxan, Po- lydimethylsiloxan, Poly(methylphenylsiloxan).Cyclomethicone (Oetamethyleyclotetrasiloxane) is advantageously used as the silicone oil to be used according to the invention. However, other silicone oils can also be used advantageously for the purposes of the present invention, for example hexamethylcyclotrisiloxane, polydimethylsiloxane, poly (methylphenylsiloxane).
Besonders vorteilhaft sind ferner Mischungen a us Cyclomethicon u nd I sotridecylisononanoat, aus Cyclomethicon und 2-Ethylhexylisostearat.Mixtures of cyclomethicone and isotridecyl isononanoate, of cyclomethicone and 2-ethylhexyl isostearate are also particularly advantageous.
Die wässrige Phase der erfindungsgemäßen Zubereitungen enthält gegebenenfalls vorteilhaft - Alkohole, Diole oder Polyole niedriger C-Zahl, sowie deren Ether, vorzugsweise Ethanol, Isopropanol, Propylenglykol, Glycerin, Ethylenglykol, Ethylenglykolmono- ethyl- oder -monobutylether, Propylenglykolmonomethyl, -monoethyl- oder -mono- butylether, Diethylenglykolmonomethyl- oder -rnonoethylether und analöge Produkte, ferner Alkohole niedriger C-Zahl, z.B. Ethanol, Isopropanol, 1 ,2- Propandiol, Glycerin sowie insbesondere ein oder mehrere Verdickungsmittel, welches oder welche vorteilhaft gewählt werden können aus der GruppeThe aqueous phase of the preparations according to the invention advantageously advantageously contains - alcohols, diols or polyols of low C number, and also their ethers, preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or - monobutyl ether, diethylene glycol monomethyl or rnonoethyl ether and analogous products, furthermore alcohols of low C number, for example Ethanol, isopropanol, 1,2-propanediol, glycerol and in particular one or more thickeners, which one or more can advantageously be selected from the group
Hnhd-01938 (203-058-1)
Siliciumdioxid, Aluminiumsilikate, Polysaccharide bzw. deren Derivate, z.B. Hyaluronsäure, Xanthangummi, Hydroxypropylmethylcellulose, besonders vorteilhaft aus der Gruppe der Polyacrylate, bevorzugt ein Polyacrylat aus der Gruppe der sogenannten Carbopole, beispielsweise Carbopole der Typen 980, ' 981 , 1382, 2984, 5984, jeweils einzeln oder in Kombination.Hnhd-01938 (203-058-1) Silicon dioxide, aluminum silicates, polysaccharides or their derivatives, for example hyaluronic acid, xanthan gum, hydroxypropylmethyl cellulose, particularly advantageously from the group of polyacrylates, preferably a polyacrylate from the group of so-called carbopoles, for example carbopoles of types 980, ' 981, 1382, 2984, 5984, individually or in combination.
Weiterhin können der erfindungsgemäßen Zubereitung UV-Filtersubstanzen zugesetzt werden. Besonders vorteilhafte bei Raumtemperatur flüssige UV-Filtersubstanzen im Sinne der vorliegenden Erfindung sind Homomenthylsalicylat (INCI: Homosalate), 2-Ethylhexyl-2- cyano-3,3-diphenylacrylat (INCI: Octocrylene), 2-Ethylhexyl-2-hydroxybenzoat (2-Ethyl- hexylsalicylat, O ctylsalicylat, I NCI: O ctyl Salicylate) und Ester der Zimtsäure, vorzugsweise 4-Methoxyzimtsäure (2-ethylhexyl)ester (2-Ethylhexyl-4-methoxycinnamat, INCI: Octyl Methoxycinnamate) und 4-Methoxyzimtsäureisopentylester (lsopentyi-4-methoxy- cinnamat, INCI: lsoamyl p-Methoxycinnamate). Bevorzugte anorganische Pigmente sind Metalloxide und/oder andere in Wasser schwerlösliche oder unlösliche Metallverbindungen, insbesondere Oxide des Titans (Ti02), Zinks (ZnO), Eisens (z. B. Fe203), Zirkoniums (ZrO2), Siliciums (SiO2), Mangans (z. B. MnO), Aluminiums (AI2O3), Cers (z. B. Ce203), Mischoxide der entsprechenden Metalle sowie Abmischungen aus solchen Oxiden sowie das Sulfat des Bariums , (BaS04). Die Pigmente können vorteilhaft im Sinne der vorliegenden Erfindung auch in Form kommerziell erhältlicher öliger oder wässriger Vordispersionen zur Anwendung kommen. Diesen Vordispersionen können vorteilhaft Dispergierhüfsmitte! und/oder Solubilisations- Vermittler zugesetzt sein. Die Pigmente können erfindungsgemäß vorteilhaft oberflächlich behandelt („gecoatet") sein, wobei beispielsweise ein hydrophiler, amphiphiler oder hydrophober Charakter gebildet werden bzw. erhalten bleiben soll. Diese Oberflächenbehandlung kann darin bestehen, dass die Pigmente nach an sich bekannten Verfahren mit einer dünnen hydrophilen und/oder hydrophoben anorganischen und/oder organischen Schicht versehen werden. Die verschiedenen Oberflächenbeschichtungen können im Sinne der vorliegenden Erfindung auch Wasser enthalten. Anorganische Oberflächenbeschichtungen im Sinne der vorliegenden Erfindung können bestehen aus Aluminiumoxid (Al203), Aluminiumhydroxid AI(OH)3, bzw. Aluminiumoxid- hydrat (auch: Alumina, CAS-Nr.: 1333-84-2), Natriumhexametaphosphat (NaP03)6, Natriummetaphosphat (NaP03)n, Siliciumdioxid (SiO2) (auch: Silica, CAS-Nr.: 7631-86- Hnhd-01938 (203-058-I)
9), oder Eisenoxid (Fe203). Diese anorganischen Oberflächenbeschichtungen können allein, in Kombination und/oder in Kombination mit organischen Beschichtungsmaterialien vorkommen. Organische Oberflächenbeschichtungen im Sinne der vorliegenden Erfindung können bestehen aus pflanzlichem oder tierischem Aluminiumstearat, pflanzlicher oder tierischer Stearinsäure, Laurinsäure, Dimethylpolysiloxan (auch: Dimethicone), M ethylpolysiloxan (Methicone), Simethicone (einem Gemisch aus Dimethylpolysiloxan mit einer durchschnittlichen Kettenlänge von 200 bis 350 Dimethylsiloxan-Einheiten und Siltcagel) oder Alginsäure. Diese organischen Oberflächenbeschichtungen können allein, inUV filter substances can also be added to the preparation according to the invention. Particularly advantageous UV filter substances which are liquid at room temperature for the purposes of the present invention are homomenthyl salicylate (INCI: homosalate), 2-ethylhexyl-2-cyano-3,3-diphenylacrylate (INCI: octocrylene), 2-ethylhexyl-2-hydroxybenzoate (2- Ethyl hexyl salicylate, octyl salicylate, I NCI: octyl salicylate) and esters of cinnamic acid, preferably 4-methoxycinnamic acid (2-ethylhexyl) ester (2-ethylhexyl 4-methoxycinnamate, INCI: octyl methoxycinnamate) and 4-methoxycinnamate acid (l-methoxycinnamate) 4-methoxycinnamate, INCI: isoamyl p-methoxycinnamate). Preferred inorganic pigments are metal oxides and / or other metal compounds which are sparingly soluble or insoluble in water, in particular oxides of titanium (Ti0 2 ), zinc (ZnO), iron (e.g. Fe 2 0 3 ), zirconium (ZrO 2 ), silicon ( SiO 2 ), manganese (e.g. MnO), aluminum (Al 2 O 3 ), cerium (e.g. Ce 2 0 3 ), mixed oxides of the corresponding metals as well as mixtures of such oxides and the sulfate of barium, (BaS0 4 ). For the purposes of the present invention, the pigments can also advantageously be used in the form of commercially available oily or aqueous predispersions. These predispersions can advantageously be dispersing agents! and / or solubilizing agents may be added. According to the invention, the pigments can advantageously be surface-treated (“coated”), for example, a hydrophilic, amphiphilic or hydrophobic character should be formed or retained. This surface treatment can consist in that the pigments are prepared using a thin hydrophilic and In the sense of the present invention, the various surface coatings can also contain water. Inorganic surface coatings in the sense of the present invention can consist of aluminum oxide (Al 2 0 3 ), aluminum hydroxide Al (OH) 3 , or aluminum oxide hydrate (also: alumina, CAS no .: 1333-84-2), sodium hexametaphosphate (NaP0 3 ) 6 , sodium metaphosphate (NaP0 3 ) n , silicon dioxide (SiO 2 ) (also: silica, CAS no. : 7631-86- Hnhd-01938 (203-058-I) 9), or iron oxide (Fe 2 0 3 ). These inorganic surface coatings can occur alone, in combination and / or in combination with organic coating materials. Organic surface coatings in the sense of the present invention can consist of vegetable or animal aluminum stearate, vegetable or animal stearic acid, lauric acid, dimethylpolysiloxane (also: dimethicone), methylpolysiloxane (methicone), simethicone (a mixture of dimethylpolysiloxane with an average chain length of 200 to 350 dimethylsiloxane -Units and Siltcagel) or alginic acid. These organic surface coatings can be used alone, in
10 Kombination und/oder in Kombination mit anorganischen Beschichtungsmaterialien vorkommen. Erfindungsgemäß geeignete Zinkoxidpartikel und Vordispersionen von Zinkoxidpartikeln sind unter folgenden Handelsbezeichnungen bei den aufgeführten Firmen erhältlich:10 combination and / or in combination with inorganic coating materials. Zinc oxide particles and predispersions of zinc oxide particles suitable according to the invention are available under the following trade names from the listed companies:
15. Geeignete Titandioxidpartikel und Vordispersionen von Titandioxidpartikeln sind unter folgenden Handelsbezeichnungen bei den aufgeführten Firmen erhältlich:15. Suitable titanium dioxide particles and predispersions of titanium dioxide particles are available under the following trade names from the companies listed:
Vorteilhafte UV-A-Filtersubstanzen im Sinne der vorliegenden Erfindung sind Dibenzoyl- methanderivate, insbesondere das 4-(tert.-Butyl)-4'-methoxydibenzoylmethan (CAS-Nr. 0 70356-09-1 ), welches von Givaudan unter der Marke Parsol® 1789 und von Merck unter der Handelsbezeichnung Eusolex® 9020 verkauft wird. Vorteilhafte weitere UV-Filtersubstanzen im Sinne der vorliegenden Erfindung sind sulfo- nierte, wasserlösliche UV-Filter, wie z. B.: • Phenylen-1 ,4-bis-(2-benzimidazyl)-3,3'-5,5'-tetrasulfonsäure und ihre Salze, beson- 25 ders die entsprechenden Natrium-, Kalium- oder Triethanolammonium-Salze, insbe-Advantageous UV-A filter substances for the purposes of the present invention are dibenzoyl methane derivatives, in particular 4- (tert-butyl) -4'-methoxydibenzoyl methane (CAS No. 0 70356-09-1), which is sold by Givaudan under the brand name Parsol ® 1789 and sold by Merck under the trade name Eusolex® 9020. Advantageous further UV filter substances in the sense of the present invention are sulfonated, water-soluble UV filters, such as. For example: • Phenylene-1,4-bis (2-benzimidazyl) -3,3'-5,5'-tetrasulfonic acid and its salts, especially the corresponding sodium, potassium or triethanolammonium salts, in particular -
Hnhd-01938 (203-058-1)
sondere das Phenylen-1 ,4-bis-(2-benzimidazyl)-3,3'-5,5'-tetrasulfonsäure-bis-natri- umsalz mit der INCI-Bezeichnung Bisimidazylate (CAS-Nr.: 180898-37-7), welches beispielsweise unter der Handelsbezeichnung Neo Heliopan AP bei Haarmann & Reimer erhältlich ist; • Salze der 2-Phenylbenzimidazol-5-sulfonsäure, wie ihr Natrium-, Kalium- oder ihr Triethanolammonium-Salz sowie die Sulfonsäure selbst mit der INCI Bezeichnung Phenylbenzimidazole Sulfonsäure (CAS.-Nr. 27503-81-7), welches beispielsweise unter der Handelsbezeichnung Eusolex 232 bei Merck oder unter Neo Heliopan Hydro bei Haarmann & Reimer erhältlich ist; • 1 ,4-di(2-oxo-10-Sulfo-3-bomylidenmethyl)-Benzol (auch: 3,3'-(1.4-Phenylendimethy- lene)-bis-(7,7-dimethyl-2-oxo-bicyclo-[2.2.1]hept-1-ylmethan Sulfonsäure) und dessen Salze (besonders die entprechenden 10-Sulfato-verbindungen, insbesondere das entsprechende Natrium-, Kalium- oder Triethanolammonium-Salz), das auch als Benzol-1 ,4-di(2-oxo-3-bomylidenmethyl-10-sulfonsäure) bezeichnet wird. Benzol- 1 ,4-di(2-oxo-3-bomylidenmethyl-10-sulfonsäure) hat die INCI-Bezeichnung Terephtalidene Dicampher Sulfonsäure (CAS.-Nr.: 90457-82-2) und ist beispielsweise unter dem Handelsnamen Mexoryl SX von der Fa. Chimex erhältlich; Sulfonsäure-Derivate des 3-Benzylidencamphers, wie z. B. 4-(2-Oxo-3-bomyliden- methyl)benzolsulfonsäure, 2-Methyl-5-(2-oxo-3-bomylidenmethyl)sulfonsäure und deren Salze.Hnhd-01938 (203-058-1) especially the phenylene-1,4-bis (2-benzimidazyl) -3,3'-5,5'-tetrasulfonic acid bis-sodium salt with the INCI name bisimidazylate (CAS No .: 180898-37-7 ), which is available, for example, from Haarmann & Reimer under the trade name Neo Heliopan AP; • Salts of 2-phenylbenzimidazole-5-sulfonic acid, such as its sodium, potassium or triethanolammonium salt and the sulfonic acid itself with the INCI name phenylbenzimidazole sulfonic acid (CAS No. 27503-81-7), which, for example, under the Trade name Eusolex 232 is available from Merck or under Neo Heliopan Hydro from Haarmann &Reimer; • 1,4-di (2-oxo-10-sulfo-3-bomylidenemethyl) benzene (also: 3,3 '- (1,4-phenylenedimethylene)) bis- (7,7-dimethyl-2-oxo- bicyclo- [2.2.1] hept-1-ylmethane sulfonic acid) and its salts (especially the corresponding 10-sulfato compounds, especially the corresponding sodium, potassium or triethanolammonium salt), which is also called benzene-1,4,4 di (2-oxo-3-bomylidenemethyl-10-sulfonic acid) Benzene-1, 4-di (2-oxo-3-bomylidenemethyl-10-sulfonic acid) has the INCI name Terephtalidene Dicampher Sulfonic Acid (CAS no .: 90457-82-2) and is available, for example, under the trade name Mexoryl SX from Chimex; sulfonic acid derivatives of 3-benzylidene camphor, such as 4- (2-oxo-3-bomylidene-methyl) benzenesulfonic acid , 2-methyl-5- (2-oxo-3-bomylidenemethyl) sulfonic acid and its salts.
Vorteilhafte UV-Filtersubstanzen im Sinne der vorliegenden Erfindung sind ferner sogenannte Breitbandfilter, d.h. Filtersubstanzen, die sowohl UV-A- als auch UV-B-Strahlung absorbieren.Advantageous UV filter substances in the sense of the present invention are also so-called broadband filters, i.e. Filter substances that absorb both UV-A and UV-B radiation.
Vorteilhafte Breitbandfilter oder UV-B-Filtersubstanzen sind beispielsweise Triazinderi- vate, wie z. B.Advantageous broadband filters or UV-B filter substances are, for example, triazine derivatives, such as. B.
• 2,4-Bis-{[4-(2-Ethyl-hexyloxy)-2-hydroxy]-phenyl}-6-(4-methoxyphenyl)-1 ,3,5-triazin (INCI: Aniso Triazin), welches unter der Handelsbezeichnung Tinosorb® S bei der CIBA-Chemikalien GmbH erhältlich ist; Diethylhexylbutylamidotriazon (INCI: Diethylhexylbutamidotriazone), welches unter der Handelsbezeichnung UVASORB HEB bei Sigma 3V erhältlich ist; 4,4',4"-(1 ,3,5-Triazin-2,4,6-triyltriimino)-tris-benzoesäure-tris(2-ethylhexylester), auch: 2,4,6-Tris-[anilino-(p-carbo-2'-ethyl-1'-hexyloxy)]-1 ,3,5-triazin (INCI: Ethylhexyl Triazone), welches von der BASF Aktiengesellschaft unter der Warenbezeichnung UVINUL® T 150 vertrieben wird. Ein vorteilhafter Breitbandfilter im Sinne der vorliegenden Erfindung ist auch, das 2,2'- Methylen-bis-(6-(2H-benzotriazol-2-yl)-4-(1 ,1 ,3,3-tetramethylbutyl)-phenol), welches• 2,4-bis - {[4- (2-ethylhexyloxy) -2-hydroxy] phenyl} -6- (4-methoxyphenyl) -1, 3,5-triazine (INCI: Aniso Triazine), which is available from CIBA-Chemicals GmbH under the trade name Tinosorb® S; Diethylhexylbutylamidotriazon (INCI: Diethylhexylbutamidotriazone), which is available under the trade name UVASORB HEB from Sigma 3V; 4,4 ', 4 "- (1,3,5-triazine-2,4,6-triyltriimino) tris-benzoic acid tris (2-ethylhexyl ester), also: 2,4,6-tris [anilino- (p-carbo-2'-ethyl-1'-hexyloxy)] - 1,3,5-triazine (INCI: Ethylhexyl Triazone), which is sold by BASF Aktiengesellschaft under the trade name UVINUL® T 150. An advantageous broadband filter in According to the present invention, the 2,2'-methylene-bis- (6- (2H-benzotriazol-2-yl) -4- (1, 1, 3,3-tetramethylbutyl) phenol), which
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unter der Handelsbezeichnung Tinosorb® M bei der CIBA-Chemikalien GmbH erhältlich ist.Hnhd-01938 (203-058-1) is available under the trade name Tinosorb® M from CIBA-Chemicals GmbH.
Vorteilhafter Breitbandfilter im Sinne der voriiegenden. Erfindung ist ferner das 2-(2H- benzotriazol-2-yl)-4-methyl-6-[2-methyl-3-[1 ,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]di- siloxanyl]propyl]-phenol (CAS-Nr.: 155633-54-8) mit der INCI-Bezeichnung Drometrizole Trisiioxane, welches unter der Handelsbezeichnung Mexoryl® XL bei der Fa. Chimex erhältlich ist.Advantageous broadband filter in the sense of the previous. Another invention is 2- (2H-benzotriazol-2-yl) -4-methyl-6- [2-methyl-3- [1, 3,3,3-tetramethyl-1 - [(trimethylsilyl) oxy] di- siloxanyl] propyl] phenol (CAS No .: 155633-54-8) with the INCI name Drometrizole Trisiioxane, which is available under the trade name Mexoryl® XL from Chimex.
Die weiteren UV-Filtersubstanzen können öllöslich oder wasserlöslich sein. Vorteilhafte öllösliche UV-B- und/oder Breitband-Filtersubstanzen im Sinne der vorlie- genden Erfindung sind z. B.:The other UV filter substances can be oil-soluble or water-soluble. Advantageous oil-soluble UV-B and / or broadband filter substances in the sense of the present invention are e.g. B .:
• 3-Benzylidencampher-Derivate, vorzugsweise 3-(4-Methylbenzyliden)campher, 3- Benzylidencampher;• 3-benzylidene camphor derivatives, preferably 3- (4-methylbenzylidene) camphor, 3-benzylidene camphor;
■ 4-Aminobenzoesäure-Derivate, vorzugsweise 4-(Dimethylamino)-benzoesäure(2- ethylhexyl)ester, 4-(Dimethylamino)benzoesäureamylester; ■ Derivate des Benzophenons, vorzugsweise 2-Hydroxy-4-methoxybenzophenon, 2- Hydroxy-4-methoxy-4'-methylbenzophenon, 2,2'-Dihydroxy-4-methoxybenzophenon ■ 4-aminobenzoic acid derivatives, preferably 4- (dimethylamino) benzoic acid (2-ethylhexyl) ester, 4- (dimethylamino) benzoic acid amyl ester; ■ Derivatives of benzophenone, preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone
■ sowie an Polymere gebundene UV-Filter. ■ and UV filters bound to polymers.
* 3-(4-(2,2-bis Ethoxycarbonylvinyl)-phenoxy)propenyl)- methoxysiloxan/Dimethylsiloxan - Copolymer welches beispielsweise unter der Handelsbezeichnung Parsol® SLX bei Hoffmann La Röche erhältlich ist.* 3- (4- (2,2-bis-ethoxycarbonylvinyl) phenoxy) propenyl) methoxysiloxane / dimethylsiloxane copolymer which is available, for example, from Hoffmann La Röche under the trade name Parsol® SLX.
Vorteilhafte wasserlösliche Filtersubstanzen sind z. B.:Advantageous water-soluble filter substances are e.g. B .:
Sulfonsäure-Derivate des 3-Benzylidencamphers, wie z. B. 4-(2-Oxo-3-bornylidenme- thyl)benzolsulfonsäure, 2-Methyl-5-(2-oxo-3-bornylidenmethyl)sulfonsäure und deren Salze. Eine weiterere erfindungsgemäß vorteilhaft zu verwendende Lichtschutzfiltersubstanz ist das Ethylhexyl-2-cyano-3,3-diphenylacrylat (Octocrylen), welches von BASF unter der Bezeichnung Uvinul® N 539 erhältlich ist.Sulfonic acid derivatives of 3-benzylidene camphor, such as. B. 4- (2-oxo-3-bornylidene methyl) benzenesulfonic acid, 2-methyl-5- (2-oxo-3-bornylidene methyl) sulfonic acid and salts thereof. A further light protection filter substance according to the invention to be used advantageously is ethylhexyl-2-cyano-3,3-diphenylacrylate, obtainable (octocrylene) from BASF under the name Uvinul ® N 539th
Besonders vorteilhafte Zubereitungen im Sinne der vorliegenden Erfindung, die sich durch einen hohen bzw. sehr hohen UV-A- und/oder UV-B-Schutz auszeichnen, enthalten neben der oder den erfindungsgemäßen Filtersubstanz(en) bevorzugt ferner weitere UV-A- und/oder Breitbandfilter, insbesondere Dibenzoylmethanderivate [beispielsweise das 4-(tert.-Butyl)-4'-methoxydibenzoylmethan], Phenylen-1 ,4-bis-(2- benzimidazyl)-3,3'-5,5'-tetrasulfonsäure und/oder ihre Salze, das 1 ,4-di(2-oxo-10-Sulfo- 3-bornylidenmethyl)-Benzol und/oder dessen Salze und/oder das 2,4-Bis-{[4-(2-Ethyl-Particularly advantageous preparations within the meaning of the present invention, which are distinguished by a high or very high UV-A and / or UV-B protection, preferably contain further UV-A and in addition to the filter substance (s) according to the invention / or broadband filter, in particular dibenzoylmethane derivatives [for example the 4- (tert-butyl) -4'-methoxydibenzoylmethane], phenylene-1, 4-bis- (2-benzimidazyl) -3,3'-5,5'-tetrasulfonic acid and / or their salts, the 1,4-di (2-oxo-10-sulfo-3-bornylidenemethyl) benzene and / or its salts and / or the 2,4-bis - {[4- (2-ethyl-
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hexyloxy)-2-hydrqxy]-phenyl}-6-(4-methoxyphenyl)-1 ,3,5-triazin, jeweils einzeln oder in beliebigen Kombinationen miteinander.Hnhd-01938 (203-058-1) hexyloxy) -2-hydrqxy] -phenyl} -6- (4-methoxyphenyl) -1, 3,5-triazine, in each case individually or in any combination with one another.
Erfindungsgemäß besonders vorteilhaft sind ferner Benzoxazol-Derivate wie insbesondere das 2,4-bis-[5-1 (dimethylpropyl)benzoxazol-2-yl-(4-phenyl)-imino]-6-(2- ethylhexyl)-imino-1 ,3,5-triazin mit der CAS Nr. 288254-16-0, weiches beispielsweise unter der Handelsbezeichnung Uvasorb® K2A erhältlich ist, sowie Hydroxybenzophenone wie insbesondere der 2-(4'-Diethylamino-2'-hydoxybenzoyl)- benzoesäurehexylester oder auch Aminobenzophenon, welcher unter dem Uvinul A Plus erhältlich ist.Benzoxazole derivatives such as, in particular, 2,4-bis- [5-1 (dimethylpropyl) benzoxazol-2-yl- (4-phenyl) -imino] -6- (2-ethylhexyl) -imino-1 are also particularly advantageous according to the invention , 3,5-triazine with the CAS No. 288254-16-0, which is available, for example, under the trade name Uvasorb® K2A, and hydroxybenzophenones such as, in particular, the 2- (4'-diethylamino-2'-hydoxybenzoyl) benzoic acid hexyl ester or else Aminobenzophenone, which is available under the Uvinul A Plus.
Die Liste der genannten UV-Filter, die im Sinne der voriiegenden Erfindung eingesetzt werden können, soll selbstverständlich nicht limitierend sein.The list of the UV filters mentioned, which can be used in the sense of the present invention, should of course not be limiting.
Vorteilhaft enthalten die •erfindungsgemäßen Zubereitungen die Substanzen, die UV- Strahlung im UV-A- und/oder UV-B-Bereich absorbieren, in einer Gesamtmenge von z. B. 0,1 Gew.-% bis 30 Gew.-%, vorzugsweise 0,5 bis 20 Gew.-%, insbesondere 1 ,0 bis 15,0 Gew.-%, jeweils bezogen auf das Gesamtgewicht der Zubereitungen, um kosmetische Zubereitungen zur Verfügung zu stellen, die das Haar bzw, die Haut vor dem gesamten Bereich der ultravioletten Strahlung schützen. Sie können auch als Sonnen- Schutzmittel fürs Haar dienen.The preparations according to the invention advantageously contain the substances which absorb UV radiation in the UV-A and / or UV-B range in a total amount of, for. B. 0.1 wt .-% to 30 wt .-%, preferably 0.5 to 20 wt .-%, in particular 1, 0 to 15.0 wt .-%, each based on the total weight of the preparations to cosmetic To provide preparations that protect the hair or the skin from the entire range of ultraviolet radiation. They can also serve as a sunscreen for the hair.
Die erfindungsgemäßen Formulierungen können vorteilhaft, wenngleich nicht zwingend, auch in Kombination mit UV-Strahlung - sei es mit künstlich erzeugten oder natürlichen ultravioletten Strahlen - verwendet werden, beispielsweise um die natürliche Bräunung noch zu steigern oder aber um eine besonders lang anhaltende Bräunung zu erreichen.The formulations according to the invention can advantageously, although not necessarily, also be used in combination with UV radiation - be it with artificially generated or natural ultraviolet rays - for example in order to increase natural tanning or to achieve a particularly long-lasting tanning.
Zur Anwendung werden die erfi dungsgemäßen kosmetischen und dermatologischen Formulierungen in der für Kosmetika üblichen Weise auf die Haut und/oder die Haare in ausreichender Menge aufgebracht.For use, the cosmetic and dermatological formulations according to the invention are applied to the skin and / or the hair in a sufficient amount in the manner customary for cosmetics.
Nach den ausführlichen Ausführungen ist die Verwendung des erfindungsgemäßen Mittels, insbesondere einer kosmetischen und/oder dermatologischen Zubereitung, bevorzugt - als wässriges System und/oder Tensidzubereitung zur Reinigung und Pflege der Haut und/oder der Haare,According to the detailed explanations, the use of the agent according to the invention, in particular a cosmetic and / or dermatological preparation, is preferred - as an aqueous system and / or surfactant preparation for cleaning and care of the skin and / or hair,
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- als Mehrfachemulsion, Mikroemulsion, Pickering-Emulsion oder sprühbare Emulsion, - als Presun-, einer Sonnenschutz- oder einer Aftersunformulierung, - zur topischen Anwendung auf Haut und/oder Haaren, - zur Bräunung der Haut, - zur Pflege der Haut, - zum Schutz der Haut und/oder dem Haar vor schädigenden UV-Strahlen, . - zur Steigerung der Melaninsynthese in der Haut, . - zur Verlängerung der Braunfärbung^ der Haut, - zum Schutz der Haut vor oxidativem Streß, - zum Schutz der Haut vor chronologischer und lichtbedingter Hautalterung, - zur Intensivierung der Haarfarbe, - zur Verhinderung d.es Ergrauen der Haare und/oder zum Schutz, vor dem sonnenlichtbedingtem Ausbleichen der Haare, - als Duschgel, Shampoo, Conditioner, Haarpflegekur, Haarspülung, Haartonic, Haarspray, Make-up, Hautschutz-, Gesichts-, Reinigungs-, Sonnenschutz-, Nähr- , Tages- oder Nachtcreme, -gel, oder -lotion oder Cleansing-Zubereitung.Hnhd-01938 (203-058-1) - as a multiple emulsion, microemulsion, Pickering emulsion or sprayable emulsion, - as a presun, a sunscreen or an aftersun formulation, - for topical use on skin and / or hair, - for tanning the skin, - for skin care, - for Protection of the skin and / or hair from damaging UV rays,. - to increase melanin synthesis in the skin,. - to prolong the brown color ^ of the skin, - to protect the skin from oxidative stress, - to protect the skin from chronological and light-related aging, - to intensify the hair color, - to prevent graying of the hair and / or to protect, before the hair fades due to sunlight - as a shower gel, shampoo, conditioner, hair care regimen, hair conditioner, hair tonic, hair spray, make-up, skin protection, face, cleaning, sun protection, nutritional, day or night cream, gel, or lotion or cleansing preparation.
Die erfindungsgemäßen Verbindungen können ebenso Bestandteil einer Polymermatrix, einer Haut- und/oder Wundauflage, eines Pflasters, eines Tuchs oder Pads, eines Sprays oder auf oder in Textilien, wie Bandagen oder Badetextilien, aufgebracht sein.The compounds according to the invention can likewise be a constituent of a polymer matrix, a skin and / or wound dressing, a plaster, a cloth or pad, a spray or on or in textiles, such as bandages or bath textiles.
So ist die Einarbeitung der Verbindungen in Polymermatrizes, wie beispielsweise Polyurethanmatrizes,, problemlos möglich. Ähnlich der bekannter. Wirkstofffreisetzung - können die Verbindungen aus der Matrix an die Haut oder dem Haar abgegeben werden und ermöglichen dort ihre vorteilhaften Eigenschaften. In einer Pflasterapplikation oder aufgebracht auf Textilien, Bandagen oder ähnlichem können die Verbindungen in die Haut eindringen und den gewünschten Schutz, Pflege oder Bräunungseffekt bewirken.The incorporation of the compounds into polymer matrices, such as, for example, polyurethane matrices, is thus possible without any problems. Similar to that known. Active ingredient release - the compounds from the matrix can be released to the skin or hair and enable their advantageous properties there. In a plaster application or applied to textiles, bandages or the like, the compounds can penetrate the skin and bring about the desired protection, care or tanning effect.
Eine Applikation als Spray ist bevorzugt, da hier die Verbindungen lediglich mit geeigneten Aerosolen oder Gasen vermischt werden müssen.Application as a spray is preferred since the compounds only have to be mixed with suitable aerosols or gases.
Alle Mengenangaben, Anteile und Prozentanteile sind, soweit nicht anders angegeben, auf das Gewicht und die Gesamtmenge bzw. auf das Gesamtgewicht der Zubereitungen bezogen.Unless otherwise stated, all quantities, parts and percentages are based on the weight and the total amount or on the total weight of the preparations.
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Beispiele 1. PIT- EmulsionenHnhd-01938 (203-058-1) Examples 1. PIT emulsions
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3. OW-Creme3. OW cream
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10. Sprayformulierunq 10. Spray formulation
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11. DuschbadHnhd-01938 (203-058-1) 11. Shower room
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14. Conditioner-Shampoo mit Perlglanz14. Pearlescent conditioner shampoo
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Wasser, VES (vollentsalzt) ad 100,0 ad 100,0 ad 100,0 Der pH-Wert wird auf 6 eingestellt. Hnhd-01938 (203-058-1) Water, VES (fully desalinated) ad 100.0 ad 100.0 ad 100.0 The pH is adjusted to 6.
16. klares Liqht-Shampoo mit Volumeneffekt16. Clear Liqht shampoo with volume effect
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Claims
1. M ittel zur Anwendung auf der Haut und/oder dem Haar, dadurch gekennzeichnet, dass das Mittel ein oder mehrere 4-fach substituierte Cyclohexen-Verbindungen der Struktur1. Means for use on the skin and / or hair, characterized in that the agent has one or more 4-times substituted cyclohexene compounds of the structure
enthält, wobei die Reste R1 , R2 und/oder R5 gewählt werden aus der Gruppe Wasserstoff, Methyl, Ethyl, Propyl, iso-Propyl, Butyl, tert-Butyl, Hydroymethyl, Hydroxyethyl, Hydroxypropyl, Hydroxy u nd/oder C arbonsäurealkylester mit Alkylresten gewählt aus Methyl, Ethyl, Propyl oder Butyl, R3 gewählt wird aus der Gruppe der Verbindungsreste der Struktur (I) mit (I) contains, wherein the radicals R1, R2 and / or R5 are selected from the group hydrogen, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, hydroymethyl, hydroxyethyl, hydroxypropyl, hydroxy and / or alkyl carboxylate with alkyl radicals selected from methyl, ethyl, propyl or butyl, R3 is selected from the group consisting of the compound residues of structure (I) with (I)
R6 und/oder R7 gewählt werden aus der Gruppe Wasserstoff, Methyl, Ethyl, Propyl, iso-Propyl, Butyl, tert-Butyl, Hydroymethyl, Hydroxyethyl, Hydroxypropyl, Hydroxy oder Carbonsäurealkylester, wobei der Alkylrest gewählt wird aus Methyl, Ethyl, Propyl oder Butyl, R4 gewählt wird aus Carbonylsauerstoff, - Aminosäureresten Ala, Ser, Gly, Val, Leu, lle, Pro, Trp, Phe, Met Tyr, Thr, Cys, Asn, Asp, Glu, Lys, Arg, Gin, H, Orn, Sar, Hyl, Hyp, Hse oder Hey, - Resten der Struktur N-(CH2)x-OH, N-(CHR9)X-CH20H, N-(CHR9)x-OH, N-(CH2)X- OCOMe, wobei jeweils x = 1 - 10, N-OH, oder - Resten der StrukturR6 and / or R7 are selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, hydroymethyl, hydroxyethyl, hydroxypropyl, hydroxy or alkyl carboxylate, the alkyl radical being selected from methyl, ethyl, propyl or Butyl, R4 is chosen from carbonyl oxygen, - amino acid residues Ala, Ser, Gly, Val, Leu, lle, Pro, Trp, Phe, Met Tyr, Thr, Cys, Asn, Asp, Glu, Lys, Arg, Gin, H, Orn , Sar, Hyl, Hyp, Hse or Hey, - residues of the structure N- (CH 2 ) x -OH, N- (CHR9) X -CH20H, N- (CHR9) x -OH, N- (CH 2 ) X - OCOMe, where x = 1 - 10, N-OH, or - residues of the structure
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0 R9 gewählt wird aus Wasserstoff und/oder Hydroxy; R11 gewählt wird aus Methyl-, Hydroxymethyl-, Wasserstoff, Prop-2-yl-, Isobutyl-, But-2-yl-, Pyrrolidin-1 ,2-diyl-, 1H-lndol-3-y!-methyl-, Benzyl-; 2-(Methylthio)ethyl-, 4- Hydroxy-benzyl-, 1 -Hydroxyethyl-, Mercaptomethyl-, 2-Amino-2-oxoethyl-, Carboxymethyl-, Carboxyethyl-, 4-Aminobutyl-, 3-{[Amino(imino)methyl]amϊno}propyl-, 3-Amino-3-oxopropyl-, Wasserstoff und N-Me, 3-Aminopropyl-, Ethyl-, 1H-lmidazol-4- yl-methyl-, Butyl-, Propyl-, 4-Amino-3-hydroxy-butyl-, 4-Hydroxy-pyrrolidin-1,2-diyl-, Hydroxyethyl-, oder 2-Mercaptoethyl-, R10 gewählt wird aus Hydroxy- (-OH), - peptidiseh N-verknüpfte Aminosäurereste gewählt aus Ala, Ser, Gly, Val, Leu, lle, Pro, Trp, Phe, Met Tyr, Thr, Cys, Asn, Asp, Glu, Lys, Arg, Gin, H, Orn, Sar, Hyl, Hyp, Hse oder Hey, Resten der Struktur 0 R9 is selected from hydrogen and / or hydroxy; R11 is selected from methyl, hydroxymethyl, hydrogen, prop-2-yl, isobutyl, but-2-yl, pyrrolidin-1, 2-diyl, 1H-indol-3-y! Methyl, benzyl; 2- (methylthio) ethyl, 4-hydroxy-benzyl, 1-hydroxyethyl, mercaptomethyl, 2-amino-2-oxoethyl, carboxymethyl, carboxyethyl, 4-aminobutyl, 3 - {[amino (imino ) methyl] amϊno} propyl, 3-amino-3-oxopropyl, hydrogen and N-Me, 3-aminopropyl, ethyl, 1H-imidazol-4-yl-methyl, butyl, propyl, 4- Amino-3-hydroxy-butyl-, 4-hydroxy-pyrrolidine-1,2-diyl-, hydroxyethyl- or 2-mercaptoethyl-, R10 is selected from hydroxy- (-OH), -peptidiseh N-linked amino acid residues selected from Ala, Ser, Gly, Val, Leu, lle, Pro, Trp, Phe, Met Tyr, Thr, Cys, Asn, Asp, Glu, Lys, Arg, Gin, H, Orn, Sar, Hyl, Hyp, Hse or Hey , Remains of the structure
mit b = 1 - 6, oder R12 gewählt wird aus Mono- bis Polysaccharide, bevorzugt einheitliche und/oder gemischte Mono-, Di- oder Trisaccharide, bevorzugt Glucose, Glycerose, Erythrose, Threose, Ribose, Arabinose, Lyxose, Xylose, Allose, Altrose, Galactose, Gulose, Idose, Mannose oder Talose, wobei Verbindungen 9-Retinal der Strukturformel with b = 1 - 6, or R12 is selected from mono- to polysaccharides, preferably uniform and / or mixed mono-, di- or trisaccharides, preferably glucose, glycerose, erythrose, threose, ribose, arabinose, lyxose, xylose, allose, altrose, galactose, gulose, idose, Mannose or Talose, with compounds 9-retinal of the structural formula
- Retinal Derivate der Struktur- Retinal derivatives of the structure
Hnhd-0 938 (203-058-1) mit Ra und/oder Rb = Alkyl oder gesättigte oder ungesättigte Alkoxygruppen und 9-Retinal-alkanolamin Schiffsche Base der StrukturformelHnhd-0 938 (203-058-1) with Ra and / or Rb = alkyl or saturated or unsaturated alkoxy groups and 9-retinal-alkanolamine Schiff base of the structural formula
wobei R = R'(OH)n verzweigte oder unverzweigte Alkanole, mit R'= C1 bis C20 Kohlenwasserstoffrest und n = 1 - 5, darstellen, aus der Gruppe der erfindungsgemäßen 4-fach substituierten Cyclohexen Verbindungen ausgenommen sind. where R = R ' (OH) n are branched or unbranched alkanols, with R ' = C1 to C20 hydrocarbon radical and n = 1-5, are excluded from the group of the 4-times substituted cyclohexene compounds according to the invention.
2. M ittel nach Anspruch 1 zur Steigerung der Hautbräunung und/oder Melanin-Synthese in der Haut und/oder dem Haar.2. Means according to claim 1 for increasing skin tanning and / or melanin synthesis in the skin and / or hair.
3. Mittel nach Anspruch 1 oder 2, dadurch gekennzeichnet, dass das Mittel eine kosmetische und/oder dermatologische Zubereitung, eine Polymermatrix, eine Haut- und/oder Wundauflage, ein Pflaster, ein Tuch oder Pad, ein Spray oder eine Textilie ist.3. Composition according to claim 1 or 2, characterized in that the agent is a cosmetic and / or dermatological preparation, a polymer matrix, a skin and / or wound dressing, a plaster, a cloth or pad, a spray or a textile.
4. Mittel nach Anspruch 3, dadurch gekennzeichnet, dass das Mittel eine kosmetische und/oder dermatologische Zubereitung ist.4. Agent according to claim 3, characterized in that the agent is a cosmetic and / or dermatological preparation.
5. M ittel nach einem der vorstehenden Ansprüche, dadurch gekennzeichnet, dass - R1 , R2, R5, R6 und/oder R7 Methylreste sind und - R4 gewählt wird aus den Aminosäureresten Ala, Ser oder Gly.5. Means according to one of the preceding claims, characterized in that - R1, R2, R5, R6 and / or R7 are methyl residues and - R4 is selected from the amino acid residues Ala, Ser or Gly.
6. Mittel nach einem der vorstehenden Ansprüche, dadurch gekennzeichnet, dass ein oder mehrere 4-fach substituierte Cyclohexen-Verbindungen gewählt werden aus /V- 3,7-Dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tretraen-1- ylidenejalanine, (1£,2£,4£,6£,8£)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1- yl)nona-2,4,6,8-tetraenal oxime, 2-{[(1£,2£,4£,6£,8£)-3,7-dimethyl-9-(2,6,6-6. Agent according to one of the preceding claims, characterized in that one or more 4-times substituted cyclohexene compounds are selected from / V- 3,7-dimethyl-9- (2,6,6-trimethylcyclohex-1-en- 1-yl) nona-2,4,6,8-tretraen-1-ylidenejalanine, (£ 1, £ 2, £ 4, £ 6, £ 8) -3,7-dimethyl-9- (2,6, 6-trimethylcyclohex-1-en-1-yl) nona-2,4,6,8-tetraenal oxime, 2 - {[(£ 1, £ 2, £ 4, £ 6, £ 8) -3.7- dimethyl-9- (2,6,6-
Hnhd-01938 (203-058-I) trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ylidene]amino}ethanol, 1- {[(1 £,2£,4£,6£,8£)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1 -en-1 -yl)nona-2,4,6,8- tetraen-1 -ylidene]amino}propane-1 ,2,3-triol, /V-[(2£,4£,6£,8£)-3,7-dimethyl-9-(2,6,6- trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ylidene]-L-alanyl-L-alanine, Λ/- [(2£,4£,6£,8£)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8- tetraen-1 -ylidene]-L-seryl-L-serine und/oder Acetyl-Retinyliminoethanol.Hnhd-01938 (203-058-I) trimethylcyclohex-1-en-1-yl) nona-2,4,6,8-tetraen-1-ylidenes] amino} ethanol, 1- {[(£ 1, £ 2, £ 4, £ 6, £ 8) -3,7-dimethyl-9- (2,6,6-trimethylcyclohex-1-en-1-yl) nona-2,4,6,8-tetraen-1-ylidenes] amino} propane-1, 2, 3-triol, / V - [(£ 2, £ 4, £ 6, £ 8) -3,7-dimethyl-9- (2,6,6-trimethylcyclohex-1-en-1-yl) nona-2 , 4,6,8-tetraen-1-ylidenes] -L-alanyl-L-alanines, Λ / - [(£ 2, £ 4, £ 6, £ 8) -3,7-dimethyl-9- (2nd , 6,6-trimethylcyclohex-1-en-1-yl) nona-2,4,6,8-tetraen-1-ylidenes] -L-seryl-L-serines and / or acetyl-retinyliminoethanol.
7. Mittel nach einem der vorstehenden Ansprüche, dadurch gekennzeichnet, dass der Gehalt an 4-fach substituierten Cyclohexen-Verbindungen zwischen 0,0001 und 30 Gew.%, insbesondere zwischen 0,01 und 10 Gew.%, besonders vorteilhaft zwischen 0,02 und 2 Gew.%, bezogen auf das Gesamtgewicht des Mitteis, bevorzugt der kosmetischen Zubereitung, beträgt.7. Agent according to one of the preceding claims, characterized in that the content of tetrasubstituted cyclohexene compounds is between 0.0001 and 30% by weight, in particular between 0.01 and 10% by weight, particularly advantageously between 0.02 and 2% by weight, based on the total weight of the medium, preferably the cosmetic preparation.
8. M ittel nach einem der vorstehenden Ansprüchen, dadurch gekennzeichnet, dass die 4-fach substituierten Cyclohexen-Verbindungen in verkapselter Form enthalten sind.8. Means according to one of the preceding claims, characterized in that the 4-times substituted cyclohexene compounds are contained in encapsulated form.
9. M ittel nach Anspruch 8, dadurch gekennzeichnet, dass das Verkapselungsmaterial . aus Kollagenmatrices, cyclischen Oligosacchariden, alpha-, beta-, HP-beta-, rando - Me-beta- oder gamma-Cyclodextrin, Cellulose, Gelatine, Wachsmatrices oder Liposomen besteht.9. Means according to claim 8, characterized in that the encapsulation material. consists of collagen matrices, cyclic oligosaccharides, alpha-, beta-, HP-beta-, rando-me-beta- or gamma-cyclodextrin, cellulose, gelatin, wax matrices or liposomes.
10. Mittel nach einem der Ansprüche 1 bis 9, dadurch gekennzeichnet, dass zusätzlich mindestens ein UVA-Filter und/oder mindestens ein UVB-Filter und/oder mindestens ein anorganisches- Pigment, bevorzugt ein -anorganisches Mikropigment; enthalten ist.10. Agent according to one of claims 1 to 9, characterized in that in addition at least one UVA filter and / or at least one UVB filter and / or at least one inorganic pigment, preferably an inorganic micropigment; is included.
11. Mittel nach einem der vorstehenden Ansprüche, dadurch gekennzeichnet, dass zusätzlich Antioxidantien mit einem Anteil von 0,001 bis 30 Gew.%, besonders bevorzugt .0,05 - 20 Gew.%, insbesondere 0,1 - 10 Gew.%, bezogen auf das Gesamtgewicht des Mittels, bevorzugt einer kosmetischen Zubereitung, zugesetzt sind.11. Agent according to one of the preceding claims, characterized in that additionally antioxidants in a proportion of 0.001 to 30% by weight, particularly preferably .0.05-20% by weight, in particular 0.1-10% by weight, based on the total weight of the agent, preferably a cosmetic preparation, are added.
12. Kosmetische und/oder dermatologische Zubereitung nach einem der Ansprüche 3 bis 11 , dadurch gekennzeichnet, dass zusätzlich Konservierungsmittel, Bakterizide, Parfüme, Substanzen zum Verhindern des Schäumens, Farbstoffe, Füllstoffe,12. Cosmetic and / or dermatological preparation according to one of claims 3 to 11, characterized in that in addition preservatives, bactericides, perfumes, substances for preventing foaming, dyes, fillers,
Hnhd-01938 (203-058-I) Pigmente, die eine färbende Wirkung haben, Verdickungsmittel, anfeuchtende und/oder feuchthaltende Substanzen, Fette, Öle, Wachse, Alkohole, Polyole, Polymere, Schaumstabilisatoren, Elektrolyte, organische Lösungsmittel, Silikonderivate, Moisturizer, Vitamine, Proteine, Lichtschutzmittel, Stabilisatoren, Insektenrepellentien, Wasser, Salze, antimikrobiell, proteolytisch oder keratolytisch wirksame Substanzen, Medikamente oder andere übliche Bestandteile einer kosmetischen oder dermatologischen Formulierung enthalten sind.Hnhd-01938 (203-058-I) Pigments that have a coloring effect, thickeners, moisturizing and / or moisturizing substances, fats, oils, waxes, alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents, silicone derivatives, moisturizers, vitamins, proteins, light stabilizers, stabilizers, insect repellents, Water, salts, antimicrobial, proteolytically or keratolytically active substances, medications or other usual components of a cosmetic or dermatological formulation are contained.
13. Zubereitung nach Anspruch 12, dadurch gekennzeichnet, dass Glycerin als Moisturizer im Bereich von 0,05 - 30 Gew.%, besonders bevorzugt 1 - 10 Gew.%, bezogen auf d ie Gesamtmasse der Zubereitung, zugesetzt ist.13. Preparation according to claim 12, characterized in that glycerin is added as a moisturizer in the range of 0.05-30% by weight, particularly preferably 1-10% by weight, based on the total mass of the preparation.
14. Kosmetische und/oder dermatologische Zubereitung nach einem der Ansprüche 3 bis 13 in Kombinationen mit - Wirkstoffen, die den Zustand der Haut positiv beeinflussen, insbesondere Wirkstoffe zur positiven Beeinflussung . der Altershaut, insbesondere in Kombination mit Biochinone, insbesondere Ubichinon Q10, Kreatin, Kreatinin, Camitin, Biotin, Isoflavon, Cardiolipin, Liponsäure, Anti Freezing Proteine, Hopfen- und Hopfen-Malz-Extrakte, - fördernden Mitteln zur Restrukturierung des Bindegewebes, insbesondere Isoflavonoide, - Wirkstoffen zur Unterstützung der Hautfunktionen bei trockener Haut, insbesondere Vitamin C, Biotin, Camitin, Kreatin, Propionsäure, Grüntee- Extrakte,. Eukalyptusöl, Harnstoff — und Mineralsalze,- insbesondere- -NaC r" Meeresmineralien sowie Osmolyte, - Wirkstoffen zur Linderung und/oder positiven Beeinflussung von irritativen Hautzuständen, insbesondere Sericoside, verschiedene Extrakte des Süssholzes , L icochalcone, i nsbesondere L icochalcone A , S ilymarin, Silyphos, Dexpanthenol, - Inhibitoren des Prostaglandinstoffwechsels, insbesondere der Cyciooxygenase und des Leukotrienstoffwechsels, insbesondere der 5-Lipoxyaenase oder 5- Lipoxvgenase Inhibitor Proteins, FLAP, - Modulatoren der Pigmentierung, insbesonder Tyrosinsulfat, Dioic acid (8- Hexadecen- 1 ,16-dicarbonsäure, Liponsäure, Liponamid, verschiedene Extrakte des Süssholzes, Kojisäure, Hydrochinon, Arbutin, Fruchtsäuren, insbesondere14. Cosmetic and / or dermatological preparation according to one of claims 3 to 13 in combinations with - active substances which have a positive influence on the condition of the skin, in particular active substances for positive influence. the aging skin, especially in combination with bioquinones, especially ubiquinone Q10, creatine, creatinine, camitin, biotin, isoflavone, cardiolipin, lipoic acid, anti freezing proteins, hop and hop malt extracts, - promoting agents for restructuring the connective tissue, especially isoflavonoids , - Active ingredients to support skin functions in dry skin, especially vitamin C, biotin, camitin, creatine, propionic acid, green tea extracts ,. Eucalyptus oil, urea and mineral salts, - in particular - -NaC r "marine minerals and osmolytes, - active substances for the relief and / or positive influence on irritant skin conditions, in particular sericosides, various extracts of licorice, licochalcones, in particular licochalcones A, silymarin , Silyphos, dexpanthenol, - inhibitors of prostaglandin metabolism, in particular cyciooxygenase and leukotriene metabolism, in particular 5-lipoxyenase or 5-lipoxvgenase inhibitor protein, FLAP, - pigmentation modulators, in particular tyrosine sulfate, dioic acid (8-hexadecene-1, 16 dicarboxylic acid, lipoic acid, liponamide, various extracts of liquorice, kojic acid, hydroquinone, arbutin, fruit acids, in particular
Hn d-01938 (203-058-I) Alpha-Hydroxy-Säuren (AHAs), Bearberry (Uvae ursi), Ursolsäure, Ascorbinsäure. Grüntee-Extrakte, Aminoguanidin, Pyridoxamin und/oder - Wirkstoffen, die eine verstärkte oder schnellere Bräunung der Haut herbeiführen, insbesonder Advanced Glycation Endproducts (AGE), Lipofuscine, NukleinsäureOligonukleotide, Purine, Pyrimidine, NO-freisetzende Substanzen.Hn d-01938 (203-058-I) Alpha Hydroxy Acids (AHAs), Bearberry (Uvae ursi), Ursolic Acid, Ascorbic Acid. Green tea extracts, aminoguanidine, pyridoxamine and / or active ingredients that bring about an intensified or faster tanning of the skin, in particular advanced glycation end products (AGE), lipofuscins, nucleic acid oligonucleotides, purines, pyrimidines, NO-releasing substances.
15. Verwendung des Mittels nach einem der Ansprüche 1 bis 14 in einem oder als wässriges System und/oder Tensidzuhereitung zur Reinigung und/oder Pflege der Haut und/oder der Haare.15. Use of the agent according to one of claims 1 to 14 in or as an aqueous system and / or surfactant preparation for cleaning and / or care of the skin and / or hair.
16. Verwendung einer Zubereitung nach einem der Ansprüche 3 bis 14 als Mehrfachemulsion, Mikroemulsion, Pickering-Emulsion oder sprühbare Emulsion.16. Use of a preparation according to one of claims 3 to 14 as a multiple emulsion, microemulsion, Pickering emulsion or sprayable emulsion.
17. Verwendung einer Zubereitung nach einem der Ansprüche 3 bis 14 .als Presun-, einer Sonnenschutz- oder einer Aftersunformulierung.17. Use of a preparation according to one of claims 3 to 14. As a presun, a sunscreen or an aftersun formulation.
18. Verwendung des Mittels nach einem der Ansprüche 1 bis 14 zur topischen Anwendung auf Haut und/oder Haaren.18. Use of the agent according to one of claims 1 to 14 for topical use on skin and / or hair.
19. Verwendung des Mittels nach einem der Ansprüche 1 bis 14 zur Bräunung der Haut.19. Use of the agent according to one of claims 1 to 14 for tanning the skin.
20. Verwendung des Mittels nach einem der Ansprüche 1 bis 14 zur Pflege der Haut.20. Use of the agent according to one of claims 1 to 14 for skin care.
21. Verwendung des Mittels nach einem der Ansprüche 1 bis 14 zum Schutz der Haut und/oder dem Haar vor schädigenden UV-Strahlen.21. Use of the agent according to one of claims 1 to 14 for protecting the skin and / or the hair from damaging UV rays.
22. Verwendung des Mittels nach einem der Ansprüche 1 bis 14 zur Steigerung der Melaninsynthese in der Haut.22. Use of the agent according to one of claims 1 to 14 to increase melanin synthesis in the skin.
23. Verwendung des Mittels nach einem der Ansprüche 1 bis 14 zur Verlängerung der Braunfärbung der Haut.23. Use of the agent according to one of claims 1 to 14 for extending the brown color of the skin.
24. Verwendung des Mittels nach einem der Ansprüche 1 bis 14 zum Schutz, der Haut vor oxidativern Streß.24. Use of the agent according to any one of claims 1 to 14 for protecting the skin from oxidative stress.
Hnhd-01938 (203-058-I) Hnhd-01938 (203-058-I)
25. Verwendung des Mittels nach einem der Ansprüche 1 bis 14 zum Schutz der Haut vor chronologischer und lichtbedingter Hautalterung.25. Use of the agent according to one of claims 1 to 14 for protecting the skin from chronological and light-related skin aging.
26. Verwendung des Mittels nach einem der Ansprüche 1 bis 14 zur Intensivierung der Haarfarbe.26. Use of the agent according to one of claims 1 to 14 for intensifying the hair color.
27. Verwendung des Mittels nach einem der Ansprüche 1 bis 14 zur Verhinderung des Ergrauen der Haare und/oder zum Schutz vor dem sonnenlichtbedingtem Ausbleichen der Haare.27. Use of the agent according to one of claims 1 to 14 to prevent graying of the hair and / or to protect the hair from fading due to sunlight.
28. Verwendung der Zubereitung nach einem der Ansprüche 3 bis 14 als Duschgel, Shampoo, Conditioner, Haarpflegekur, Haarspülung, Haartonic, Haarspray, Makeup, Hautschutz-, Gesichts-, Reinigungs-, Sonnenschutz-, Nähr-, Tages- oder Nachtcreme, -gel, oder -lotion oder Cleansing-Zubereitung.28. Use of the preparation according to one of claims 3 to 14 as a shower gel, shampoo, conditioner, hair care treatment, hair rinse, hair tonic, hair spray, makeup, skin protection, face, cleaning, sun protection, nutrient, day or night cream, gel, or lotion or cleansing preparation.
Hπhd-01938 (203-058-1) Hπhd-01938 (203-058-1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10341663A DE10341663A1 (en) | 2003-09-08 | 2003-09-08 | Skin and / or hair agent containing 4-substituted cyclohexene compounds |
PCT/EP2004/007627 WO2005032506A1 (en) | 2003-09-08 | 2004-07-10 | Skin and/or hair treatment agent containing tetrasubstituted cyclohexene compounds |
Publications (1)
Publication Number | Publication Date |
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EP1677752A1 true EP1677752A1 (en) | 2006-07-12 |
Family
ID=34258537
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP04740896A Withdrawn EP1677752A1 (en) | 2003-09-08 | 2004-07-10 | Skin and/or hair treatment agent containing tetrasubstituted cyclohexene compounds |
Country Status (4)
Country | Link |
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US (1) | US20070028400A1 (en) |
EP (1) | EP1677752A1 (en) |
DE (1) | DE10341663A1 (en) |
WO (1) | WO2005032506A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106747002A (en) * | 2016-12-27 | 2017-05-31 | 刘曲波 | A kind of anti-freezing and heat-insulating mortar |
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DE102005048779A1 (en) * | 2005-10-10 | 2007-04-12 | Beiersdorf Ag | Cosmetic formulations for improving skin barrier function |
DE102006004327A1 (en) | 2006-01-31 | 2007-08-02 | Merck Patent Gmbh | New chromen-4-one derivatives useful as self-tanning agents, for increasing melanin synthesis in the skin and for protecting the skin from ultraviolet radiation |
WO2007123699A1 (en) * | 2006-03-30 | 2007-11-01 | Dana-Farber Cancer Institute, Inc. | Methods and compositions for modulating melanogenesis by using a mclr agonist |
FR2905264B1 (en) * | 2006-08-30 | 2012-12-28 | Oreal | COLORED FRAGRANCE COMPRISING THE ASSOCIATION OF A BETA COMPOUND, ALKYL BETA'-DIPHENYLACRYLATE OR ALPHA-CYANO-BETA, ALKYL BETA'-DIPHENYLACRYLATE AND AT LEAST ONE SOLUBLE ORGANIC FILTER. |
DE102006049056A1 (en) * | 2006-10-13 | 2008-04-17 | Beiersdorf Ag | Apparatus and method for the preparation of cosmetics using additional components |
US20100102142A1 (en) * | 2008-10-28 | 2010-04-29 | Daria Tagliareni | Scent dispenser assembly |
US11724134B2 (en) | 2012-11-06 | 2023-08-15 | CoLabs International Corporation | Compositions containing a cellulose derived capsule with a sunscreen active agent |
US11707421B2 (en) | 2012-11-06 | 2023-07-25 | Colabs Int'l Corp. | Compositions containing a flexible derived capsule with an active agent |
US11491088B2 (en) | 2012-11-06 | 2022-11-08 | CoLabs International Corporation | Compositions containing a capsule with a moisturizing agent |
US11690793B2 (en) | 2012-11-06 | 2023-07-04 | Colabs Int'l Corp. | Composition containing a cellulose derived capsule with a sunscreen |
US10322301B2 (en) | 2012-11-06 | 2019-06-18 | CoLabs International Corporation | Compositions containing a cellulose derived capsule with a sunscreen active agent |
WO2017139701A1 (en) * | 2016-02-10 | 2017-08-17 | CoLabs International Corporation | Compositions containing a cellulose derived capsule with a sunscreen active agent |
JP2015536985A (en) | 2012-11-06 | 2015-12-24 | コラブス インターナショナル コーポレーション | Cellulose-derived capsule-containing composition containing sunscreen |
EP3331491B1 (en) | 2015-08-04 | 2022-03-23 | ISP Investments LLC | Polymers derived from amino-functional vinyl alcohol ethers and applications thereof |
JP6979644B2 (en) * | 2017-08-30 | 2021-12-15 | 株式会社 ナチュラル | UV shielding cosmetic composition |
CN108066228B (en) * | 2018-02-09 | 2020-06-12 | 杭州纳美智康科技有限公司 | Moisturizing antibacterial shower gel and preparation method thereof |
EP3813786A4 (en) | 2018-06-27 | 2022-06-29 | Colabs International Corporation | Compositions comprising silicon dioxide-based particles including one or more agents |
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MX9201084A (en) * | 1991-04-15 | 1992-12-21 | Bristol Myers Squibb Co | HYPER PIGMENTATION OF THE SKIN |
FR2681784B1 (en) * | 1991-10-01 | 1995-06-09 | Fabre Pierre Cosmetique | DERMATOLOGICAL AND / OR COSMETOLOGICAL COMPOSITION CONTAINING RETINOUIDES AND USE OF NEW RETINOUIDES. |
US5266307A (en) * | 1992-03-31 | 1993-11-30 | The Regents Of The University Of Michigan | Retinoic acid as a skin tanning agent in persons of light skin color |
US6238650B1 (en) * | 1999-05-26 | 2001-05-29 | Sol-Gel Technologies Ltd. | Sunscreen composition containing sol-gel microcapsules |
US20020119107A1 (en) * | 2000-12-18 | 2002-08-29 | James Varani | Method for protecting and restoring skin using selective MMP inhibitors |
US6551605B2 (en) * | 2001-04-06 | 2003-04-22 | Haarmann & Reimer | Diesters or polyesters of naphthalene dicarboxylic acid as solubilizer/stabilizer for retinoids |
DE10212865B4 (en) * | 2002-03-22 | 2005-05-04 | Beiersdorf Ag | Use of 9-retinal alkanolamine Schiff base in cosmetic dermatological formulations |
-
2003
- 2003-09-08 DE DE10341663A patent/DE10341663A1/en not_active Withdrawn
-
2004
- 2004-07-10 WO PCT/EP2004/007627 patent/WO2005032506A1/en active Application Filing
- 2004-07-10 EP EP04740896A patent/EP1677752A1/en not_active Withdrawn
- 2004-07-10 US US10/571,088 patent/US20070028400A1/en not_active Abandoned
Non-Patent Citations (1)
Title |
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See references of WO2005032506A1 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106747002A (en) * | 2016-12-27 | 2017-05-31 | 刘曲波 | A kind of anti-freezing and heat-insulating mortar |
CN106747002B (en) * | 2016-12-27 | 2018-12-28 | 南京旭程建筑材料科技有限公司 | A kind of anti-freezing and heat-insulating mortar |
Also Published As
Publication number | Publication date |
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WO2005032506A1 (en) | 2005-04-14 |
US20070028400A1 (en) | 2007-02-08 |
DE10341663A1 (en) | 2005-04-07 |
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