CN1321147A - 用作防晒剂的二氢吲哚衍生物 - Google Patents
用作防晒剂的二氢吲哚衍生物 Download PDFInfo
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- CN1321147A CN1321147A CN99811691A CN99811691A CN1321147A CN 1321147 A CN1321147 A CN 1321147A CN 99811691 A CN99811691 A CN 99811691A CN 99811691 A CN99811691 A CN 99811691A CN 1321147 A CN1321147 A CN 1321147A
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- alkyl
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- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 239000011814 protection agent Substances 0.000 title abstract 2
- 230000037072 sun protection Effects 0.000 title abstract 2
- 239000001257 hydrogen Substances 0.000 claims abstract description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 32
- -1 oxalyl amido benzene class Chemical class 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 22
- 239000000516 sunscreening agent Substances 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
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- 125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 3
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
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- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- 230000001166 anti-perspirative effect Effects 0.000 description 3
- 239000003213 antiperspirant Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
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- HOVAGTYPODGVJG-UVSYOFPXSA-N (3s,5r)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol Chemical compound COC1OC(CO)[C@@H](O)C(O)[C@H]1O HOVAGTYPODGVJG-UVSYOFPXSA-N 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229940059574 pentaerithrityl Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000001024 permanent hair color Substances 0.000 description 1
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- NPCOQXAVBJJZBQ-UHFFFAOYSA-N reduced coenzyme Q9 Natural products COC1=C(O)C(C)=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)C)C(O)=C1OC NPCOQXAVBJJZBQ-UHFFFAOYSA-N 0.000 description 1
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
- A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4966—Triazines or their condensed derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an alkyl or cycloalkyl radical attached to the ring nitrogen atom
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Toxicology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Cosmetics (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明涉及式(1)的二氢吲哚衍生物作为防晒剂的应用。式(1)中R1为氢,C1-C5烷基,C1-C18烷氧基或者卤素;R2为C1-C8烷基,C5-C7环烷基,C6-C10芳基;R5为C1-C18烷基或者式(1a)的基团;R4为氢或者式(a)的基团;R5为式(b)的基团,C1-C18烷氧基或者式(1b)的基团;R6和R7各自独立分别为氢或者C1-C5烷基;R8为氢,C1-C5烷基,C5-C7环烷基,苯基,苯基-C1-C3烷基;R9为C1-C18烷基;X是卤素原子,式(1c)或式(1d)的基团,n为0或者1。
Description
本发明涉及二氢吲哚衍生物以及这些化合物作为防晒剂的应用。
二氢吲哚化合物是染料化学中为人们所熟悉的并在染料化学中被用作中间体或原料,例如3-吲哚酚在靛蓝的工业合成中作为中间体,三甲基-2-亚甲基二氢吲哚(费歇尔碱)被用作制备聚次甲基染料的原料。
令人惊奇的是某些二氢吲哚衍生物也适合于用作防晒剂。
因此本发明的目的是下式所示的二氢吲哚衍生物作为防晒剂的应用:式中R1为氢,C1-C5烷基,C1-C18烷氧基或者卤素;R2为C1-C8烷基,C5-C7环烷基,C6-C10芳基;R3为C1-C18烷基或者式(1a)所示的基团:R4为氢或者式(1b)所示的基团:R5为式(1c)所示的基团:C1-C18烷氧基或者式(1d)所示的基团:R6和R7各自独立分别为氢或者C1-C5烷基;R8为氢,C1-C5烷基,C5-C7环烷基,苯基,苯基-C1-C3烷基;R9为-C1-C18烷基;X为卤素,式(1e)或(1f)所示的基团:以及n为0或者1。
C1-C18烷基为直链的或者支链的烷基残基,如甲基,乙基,正丙基,异丙基,正丁基,仲丁基,叔丁基,戊基,异戊基或叔戊基,己基,庚基,辛基,异辛基,壬基,癸基,十一烷基,十二烷基,十四烷基,十五烷基,十六烷基,十七烷基或者十八烷基。
C1-C18烷氧基为甲氧基,乙氧基,正丙氧基,异丙氧基,正丁氧基,仲丁氧基,叔丁氧基,戊基氧基,异戊基氧基或叔戊基氧基,己基氧基,庚基氧基,辛基氧基,异辛基氧基,壬基氧基,癸基氧基,十一烷基氧基,十二烷基氧基,十四烷基氧基,十五烷基氧基,十六烷基氧基,十七烷基氧基或者十八烷基氧基。
卤素指氟或溴,尤其是氯。
C5-C7环烷基指例如环戊基,环庚基而且尤其是环己基。
C6-C10芳基指苯基或萘基。
此外,令人感兴趣的式(1)化合物是下列化合物,其中R5为C1-C18烷氧基,而且尤其是式(1h)所示的基团:此外,令人感兴趣的式(1)化合物是下列化合物,其中R5为式(1i)所示的基团,并且R8为氢或者甲基。
特别令人感兴趣的式(1)化合物还包括其中R3为C3-C18异烷基的式(1)化合物。
在式(1)到式(11)化合物中涉及到部分已知化合物,也涉及新化合物。
新化合物对应于式(12)所示化合物,其中R1为氢,C1-C5烷基,C1-C5烷氧基或者卤素;R2为C1-C5烷基,C5-C7环烷基,C6-C10芳基;R3为C1-C5烷基或者式(1a)所示的基团:R4为氢或者式(1b)所示的基团;R5为C5-C17烷氧基,式(1b)所示的基团或者式(1d)所示的基团:R9为C1-C18烷基或者R4和R5为式(1b)所示的基团。
本发明所用的二氢吲哚衍生物的制备是按已知的方法进行的,这种方法是式(13)的二氢吲哚化合物(费歇尔碱)与相应的酰氯或者与酸性CH化合物缩合得到式(1)化合物:
该缩合反应通常是在20到110℃的温度下、在惰性溶剂中进行,例如在石油醚,甲苯,二甲苯,混合二甲苯或在卤代烃,如二氯甲烷中进行反应。该反应在不用溶剂的情况下也能进行。反应时间通常为数分钟到数个小时。
式(1)所示化合物特别适合于作为UV-过滤剂,就是说保护对紫外光敏感的有机材料,尤其是保护人类和动物的皮肤和毛发免受紫外辐射损害作用。因此这些化合物适合于作为化妆品、药物和兽医制品中的防晒剂。它们既可以以溶解的状态也可以以微粉化的状态应用。
另一个发明目的是含有式(1)化合物的化妆品组合物。
用于化妆品时,假如防晒剂不溶于水,则通常其平均颗粒大小为0.02到2,优选的是0.05到1.5,而非常优选的是0.1到1.0m。本发明的不溶性防晒剂可以用常用的方法粉碎至所要求的粒度,例如用喷气磨碎机、球磨机、振荡磨碎机或锤式磨碎机将防晒剂磨细。优选地,磨碎是在助磨剂存在下进行的,助磨剂用量以UV吸收剂为基础计为0.1到30%重量,优选0.5到15%重量,所用助磨剂是如烷基化的乙烯基吡咯烷酮聚合物,乙烯基吡咯烷酮-醋酸乙烯酯共聚物,酰基合氨酸类,烷基聚葡糖苷或者尤其是磷脂。
也可以用防晒剂干粉配制化妆品。防晒剂干粉用如真空喷雾,逆流喷射干燥等已知磨碎方法进行加工。这种干粉的颗粒大小为0.1纳米到2微米。为避免聚结,在制备干粉的过程之前用一种表面活性剂将防晒剂包裹。所用表面活性剂是如阴离子型、非离子型或两性表面活性剂,象磷脂或者众所周知的聚合物,如聚乙烯基吡咯烷酮(PVP),聚丙烯酸酯等。
除本发明的UV吸收剂之外,化妆品组合物中还可以包含下列化合物组中一种或多种其它的紫外防护物质:
1.对氨基苯甲酸衍生物,如4-二甲基氨基苯甲酸-2-乙基己基酯;
2.邻羟基苯甲酸衍生物,如邻羟基苯甲酸-2-乙基己基酯;
3.二苯甲酮衍生物,如2-羟基-4-甲氧基二苯甲酮和其5-磺酸衍生物;
4.二苯甲酰基甲烷衍生物,如1-(4-叔丁基苯基)-3-(4-甲氧基苯基)丙烷-1,3-二酮;
5.二苯基丙烯酸酯,如2-乙基己基-2-氰基-3,3-二苯基丙烯酸酯和3-(苯并呋喃基)-2-氰基丙烯酸酯;
6.3-咪唑-4-基-丙烯酸及其酯;
7.苯并呋喃衍生物,尤其是在EP-A-582,189、US-A-5,338,539、US-A-5,518,713和EP-A-613,893中描述的2-(对-氨基苯基)苯并呋喃衍生物;
8.聚合的UV吸收剂,如在EP-A-709,080中描述的亚苄基丙二酸酯衍生物;
9.肉桂酸衍生物,如在US-A-5,601,811和WO97/00851中公开的4-甲氧基肉桂酸-2-乙基己基酯及异戊酯/或者肉桂酸衍生物;
10.樟脑衍生物,如3-(4’-甲基)亚苄基莰烷-2-酮,3-亚苄基莰烷-2-酮,N-[2(和4)-2-氧基莰烷-3-亚基甲基)-苄基]丙烯酰胺聚合物,3-(4’-三甲基铵基)-亚苄基莰烷-2-酮的甲基硫酸盐,3,3’-(1,4-亚苯基二次甲基)-双-(7,7-二甲基-2-氧代-双环[2.2.1]庚烷-1-甲磺酸)及其盐,3-(4’-磺基)亚苄基莰烷-2-酮及其盐;
11.三苯胺基均三嗪衍生物,如2,4,6-三苯胺-(对-Carbo-2’-乙基-1’-oxi)-1,3,5-三嗪以及在US-A-5,332,568、EP-A-517,104、EP-A-507,691、WO93/17002和EP-A-570,838中公开的UV吸收剂;
12.2-羟基苯基-苯并三唑衍生物;
13.2-苯基苯并咪唑-5-磺酸及其盐;
14.基-o-氨基苯甲酸酯;
15.无机微细颜料,如TiO2(不同包裹的);
16.N-取代的苯并咪唑,如在EP-A-O,843,995中所描述的;
17.羟苯基苯并三唑及其衍生物,尤其是硅氧烷衍生物;
18.草酰胺基苯的硅氧烷衍生物,如在EP-A-0,712,856中所描述的。
在“Sunscreens”,Eds.N.J.Lowe,N.A.Shaath,MarcelDekker,Inc.,New York and Basel中或在“Cosmetics &Toiletries(107),50ff(1992)中所描述的UV-吸收剂也可用作本发明配方中附加的紫外光防护物质。”
此外,本发明的化妆品组合物也可包含已知的抗氧剂,如氨基酸(象甘油、组氨酸、酪氨酸、色氨酸)和它们的衍生物,肽(如肌肽)及其衍生物,维生素E以及维生素A及其衍生物,维生素C的衍生物,类胡萝卜素,黄烷类及其衍生物,辅酶Q或者HALS(=受阻胺光稳定剂)化合物。
该化妆品组合物包含式(1)的防晒剂或防晒剂混合物及化妆品可配伍的助剂,防晒剂的含量占组合物总重量的0.1到15%重量,优选的是0.5到10%重量。
化妆品组合物的制备可以通过常用的方法将UV吸收剂与助剂进行物理混合来进行。常用的方法如将这些单一组分一起搅拌,尤其是利用已知的化妆品UV吸收剂的溶解性质。这些已知的化妆品UV吸收剂如OMC,水杨酸异辛基酯等。
该化妆品组合物可以制成油包水或者水包油乳液,醇包油洗剂,离子型或非离子两亲性类脂化合的囊状分散体,凝胶,硬笔(festerstift)或者气雾剂。
制成油包水或水包油乳液时,温和的化妆品助剂优选包含5到50%的油相、5到20%的乳化剂和30到90%的水。油相可包含任何一种适合于制备化妆品制剂的油,如一种或多种烃油,蜡,天然油,硅油,脂肪酸酯或者脂肪醇。优选的一元或多元醇是乙醇,异丙醇,丙二醇,己二醇,甘油和山梨醇。也可使用一种或多种烷基羧酸的二价和/或三价金属盐(碱土金属、Al3+等)。
每一种常规的乳化剂都可用于本发明的化妆品组合物中,例如一种或多种天然衍生物的乙氧基化的酯,象氢代蓖麻油的多乙氧基化的酯,或硅油乳化剂,象多元硅醇,任选地乙氧基化的脂肪酸皂,脂肪醇或脂肪酸及其多氧亚乙基衍生物,任选地多乙氧基化的脱水山梨醇酯,乙氧基化的脂肪酸或脂肪酸酯,或者是乙氧基化的甘油酯。
此外合适的乳化剂是多元醇的部分脂肪酸酯,如乙二醇,1,2-丙二醇,丙三醇,山梨醇和季戊四醇的部分脂肪酸酯,以及蛋白-脂肪酸缩合物和羊毛脂衍生物,烷基羧酸盐,烷基硫酸盐或-磺酸盐或聚乙二醇醚。此外,也可使用阴离子和非离子乳化剂的混合物或者不同HLB值的纯的非离子表面活性物质的混合物。脂肪醇-和脂肪酸聚乙二醇醚或者氧乙基化的脂肪也是常用的。
本发明的化妆品组合物也可包含其它成份,如润肤剂(Emollients),乳液稳定剂,皮肤保湿剂,晒黑促进剂,增稠剂,如黄原胶,保湿剂如甘油,防腐剂,香料和着色剂。
本发明的化妆品组合物包括各种化妆品剂型。尤其是下列所列化妆品剂型:
-皮肤护理剂,如以块状或液体皂,合成洗涤剂,洗涤膏形式存在的皮肤洗净剂;
-沐浴剂,如液体的沐浴剂(泡沫浴,乳液,淋浴剂)或固体的沐浴剂,如浴片和浴盐;
-皮肤护理剂,如润肤乳,多重乳剂或润肤油;
-身体美饰剂,如化妆脸用的日霜或粉霜,擦脸粉(松散的或压紧的),口红或唇膏;
-眼部护理剂,如眼睑膏,睫毛油,描眼膏,眼霜或定眼霜(Eye-Fix-Cremes);唇护理剂,如唇膏,唇光泽剂(Lip Gloss),唇轮廓笔;指甲护理剂,如指甲油,指甲油清除剂,指甲硬化剂或者指甲表层去除剂;
-内膜(Intim)护理剂,如内膜洗剂或内膜喷雾剂;
-脚护理剂,如洗脚液,脚粉,脚膏或脚香脂,特定的除臭剂和抑汗剂或者茧子去除剂;
-防晒剂,如日光乳,防日光洗剂,日光霜,日光油,日光阻滞剂或薄型织物(tropicals),防晒黑剂(Vorbrunungsprparate)或晒后护理剂;
-皮肤晒黑剂,如自晒黑霜;
-颜料去除剂,如皮肤增白剂或增亮剂;
-驱虫剂,如驱虫油,驱虫洗液,驱虫雾剂或者驱虫膏;
-去臭剂,如去臭喷雾剂,唧筒喷雾剂,去臭凝胶,去臭棒或去臭卷筒(roller);
-抑汗剂,如抑汗膏,抑汗霜或抑汗卷筒;
-不洁皮肤的清洁和护理剂,如合成洗涤剂(固体或液体),去皮剂或擦洗剂或面具去除剂;
-化学去毛剂(脱毛剂),如去毛粉,液体去毛剂,膏状或稠状的去毛剂,凝胶状或气雾状去毛剂;
-剃须剂,如剃须皂,有泡剃须霜,无泡剃须霜,泡沫剃须剂,凝胶剃须剂,干剃须前所用的制品或剃后洗剂;
-香味剂,如香水(古龙水、香水(Eau de Toilette),香精水(Eaude Parfum),香水香精(Parfum de Toilette),香精(Parfm)),香料油或香料霜;
-用于牙齿、镶牙和口腔护理的制剂,如牙膏,凝胶牙膏,牙粉,浓缩嗽口水,去斑嗽口液,假牙清洗剂或假牙固定剂;
-用于头毛美容的制剂,如洗发香波,定型剂,护发剂,如预处理剂,发水,发膏,发胶,发脂,头发冲洗剂,治疗湿敷剂,强力头发治疗剂,头发变形剂,如电烫制作发型(热波浪,温波浪,冷波浪型)的波浪定型剂,头发拉直剂,液体的头发定型剂,头发泡沫剂,喷发剂,金发染发剂,如过氧化氢溶液,增亮洗发剂,金发染发膏,金发染发粉,金发染发糊或油,暂时的、半暂时的或永久的染发剂,含有自氧化染料的染发剂或者天然的染发剂,如指甲花或甘菊。
所列举的这些化妆品可以不同的表现形式存在,例如
-以液体制品形式存在,如一种W/O-、O/W-、O/W/O-、W/O/W-、PIT-和所有类型的微乳液
-以凝胶的形式存在,
-以油、霜、乳或洗剂的形式存在,
-以粉、漆、片或以化妆油(Make-Ups)的形式存在,
-以棒(Stiftes)的形式存在,
-以雾剂的形式(用动力气喷雾或唧筒喷雾)或以气雾剂形式存在,
-以泡沫形式存在,或
-以膏的形式存在。
本发明的化妆品制剂以其对人类的皮肤免受阳光损害作用的极好保护而出众。
下列实施例中百分率指重量百分率,其量为纯物质的重量。制备实施例
实施例1:
10g 2-(1,3,3-三甲基二氢吲哚-2-亚基)乙醛(=费歇尔碱-醛,试剂级)在250ml石油醚(沸点范围80-110℃)中加热回流溶解。用1g过滤助剂过滤得澄清的滤液并在搅拌下慢慢冷却。16小时后在25℃温度下过滤并干燥得6g纯的、淡黄色晶体。该晶体的结构式为熔点105~106℃,在乙醇中λmax=341nm时ε=34520 l/(mol/cm);光稳定性t1/2=208小时。
实施例2:
将5g 2-(1,3,3-三甲基二氢吲哚-2-亚基)乙醛(=费歇尔-醛)溶于50ml甲苯中,然后加入5滴哌啶和0.5g 100%的醋酸,再加入5g氰基乙酸-2-乙基己基酯并在100~110℃加热回流3小时,反应过程中生成的水用分水器分出。蒸出大部分的甲苯,剩余物溶于80ml热石油醚(沸点范围80-110℃)中并过滤,滤液经缓慢冷却结晶析出式(102)化合物,该化合物在25℃下过滤,干燥得7.1g黄色结晶,熔点为75-77℃。在乙醇中λmax=434nm时ε=62081 l/(mol/cm)。元素分析C24H32N2O2(%)
C H N O计算值 75.75 8.48 7.37 8.41测得值 75.7 8.5 7.4 8.6
实施例3:
将17.3g 1,3,3-三甲基-2-亚甲基二氢吲哚(=费歇尔碱)溶于30ml二氯甲烷中,在20-32℃温度下于半小时时间内滴入14g苯甲酰氨。将反应液加热到45℃并保持此温度半小时,然后冷却到25℃,滤出析出的离析物盐酸盐。将红色滤液蒸干,剩余物用30ml丙酮和3ml水的混合溶剂重结晶得8.7g式(103)的化合物,该化合物为淡黄色晶体,熔点133-134℃。在二氧六环中λmax=377nm时ε=29427 l/(mol/cm)。应用实施例:
实施例4:水包油洗剂的制备
INCI名称 | % |
聚甘油基-3甲基葡萄糖二硬脂酸酯 | 3.0 |
油酸癸基酯 | 7.2 |
软脂酸异丙基酯 | 7.0 |
辛酸/癸酸三甘油酯 | 8.4 |
式(103)化合物 | 4.0 |
甲氧基肉桂酸辛基酯 | 5.0 |
甘油 | 3.0 |
苯氧基乙醇和(甲基,乙基,丙基,丁基)对羟基苯甲酸酯 | 0.5 |
去离子水 | 60.9 |
卡波姆 | 0.2 |
软脂酸异丙基酯 | 0.8 |
NaOH(10%) | 按需求 |
油相和水相分别加热到75-80℃并小心地混合,然后剧烈混匀并轻轻搅拌冷却至室温。
用Optometrics SPF-290分析仪(2μl/cm2的Transpore-Film)测得体外SPF值为15,满足澳大利亚的UVA-保护标准(Australian/New Zealand Standard,15/NZS 2604:1993)。
实施例5:水包油乳液的制备
INCI名称 | % | |
A | 聚甘油基-3甲基葡萄糖二硬脂酸酯 | 2.5 |
油酸癸基酯 | 7.7 | |
软脂酸异丙基酯 | 7.0 | |
维生素E乙酸酯 | 1.5 | |
辛酸/癸酸三甘油酯 | 9.5 | |
双-辛基苯酚甲氧基苯基三嗪 | 3.0 | |
式(101)的化合物 | 3.5 | |
B | 甘油 | 3.0 |
苯氧基乙醇和(甲基,乙基,丙基,丁基)对羟基苯甲酸酯 | 0.5 | |
去离子水 | 64.3 | |
C | 卡波姆 | 0.2 |
软脂酸异丙基酯 | 0.8 | |
E | NaOH(10%) | 按需求 |
C相与B相混合,然后将A相和B相分别加热至75-80℃,小心加到一起混合均匀。在缓慢搅动下冷却后用E调节pH值至7.0。
用Optometrics SPF-290分析仪(2μl/cm2的Transpore-Film)测得体外SPF值为18,满足澳大利亚的UVA-保护标准(Australian/New Zealand Standard,15/NZS 2604:1993)。
实施例6:油包水型乳液的制备
INCI名称 | %w/w |
PEG-30二聚羟基硬脂酸酯 | 3.50 |
PEG-22/十二烷基二醇共聚物 | 1.50 |
微晶蜡 | 1.00 |
氢化蓖麻油 | 1.00 |
硬脂酸镁 | 1.00 |
硬脂酸辛基酯 | 15.00 |
可可甘油酯 | 2.00 |
矿物油 | 3.00 |
苯氧基乙醇类和(甲基,乙基,丙基,丁基)对羟基苯甲酸酯 | 1.00 |
甲氧基肉桂酸辛基酯 | 5.00 |
二甲氧基硅氧烷 | 0.10 |
去离子水 | 49.90 |
尿囊素 | 0.10 |
硫酸镁 | 1.00 |
式(102)的化合物 | 5.00 |
丙二醇 | 4.00 |
亚甲基双-苯并三唑基Tetrametyl丁基苯酚(pH5.5) | 6.00 |
将油相和水相分别加热到75-80℃并小心加到一起,然后剧烈混合并轻轻搅拌冷至室温,最后在搅拌下将亚甲基双-苯并三唑基Tetrametyl丁基苯酚混入到所得乳液中。
用Optometrics SPF-290分析仪(2μ1/cm2的Transpore-Film)测得体外SPF为24。
实施例7:制备油包水乳液
INCI名称 | 制剂(A)% | 制剂(B)% |
甲氧基PEG-22/十二基二醇共聚物 | 3.00 | 3.00 |
PEG/十二烷基二醇共聚物 | 3.00 | 3.00 |
羟基二十八烷基羟基硬脂酸酯 | 3.00 | 3.00 |
硬脂酸辛基酯 | 15.00 | 15.00 |
可可甘油酯 | 2.00 | 2.00 |
矿物油 | 3.00 | 3.00 |
苯氧基乙醇类和(甲基,乙基丙基,丁基)对羟基苯甲酸酯 | 1.00 | 1.00 |
甲氧基肉桂酸辛基酯 | 4.00 | 5.00 |
二甲氧基硅氧烷 | 0.20 | 0.10 |
去离子水 | 47.70 | 43.80 |
尿囊素 | 0.10 | 0.10 |
式(102)的化合物 | 5.00 | 4.00 |
硫酸镁 | 1.00 | 1.00 |
丙二醇 | 4.00 | 4.00 |
亚甲基双-苯并三唑基Tetrametyl丁基苯酚(pH5.5)(50%的悬浮液) | 8.00 | 12.00 |
将油相和水相分别加热到75-80℃并小心地加到一起,然后剧烈混匀并在慢搅拌下冷却至室温,最后在搅拌下将亚甲基双-苯并三唑基Tetrametyl丁基苯酚混入所得乳液中。
用Optometrics SPF-290分析仪(2μl/cm2的Transpore-Film)测得体外SPF值为20(A)和28(B),都满足澳大利亚的UVA-防护标准(Australian/New Zealand Standard,15/NZS 2604:1993)。
Claims (12)
3.根据权利要求2的应用,其中R8为氢或甲基。
4.根据权利要求2的应用,其中R5为C1-C18烷氧基。
7.根据权利要求1到6之一项的应用,其中R3为C3-C18异烷基。
8.式(1)化合物用作保护人类和动物的毛发和皮肤免受紫外辐射损害作用的应用。
9.化妆品组合物,其中含有至少一种或多种权利要求1中所述的式(1)化合物以及化妆品可配伍的载体或助剂。
10.根据权利要求9的化妆品组合物,其特征在于含有其它的紫外防护物质。
11.根据权利要求9或10的化妆品组合物,其特征在于含有的其它紫外防护物质是三嗪类,草酰胺基苯类,三唑类,含有乙烯基的酰胺类或肉桂酸酰胺类。
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EP98810993.0 | 1998-10-02 | ||
EP98810993 | 1998-10-02 |
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US (2) | US6358496B1 (zh) |
EP (1) | EP1117641B1 (zh) |
JP (1) | JP2002526526A (zh) |
KR (1) | KR20010075501A (zh) |
CN (1) | CN1155569C (zh) |
AT (1) | ATE262509T1 (zh) |
AU (1) | AU5980399A (zh) |
BR (1) | BR9914255A (zh) |
DE (1) | DE59908967D1 (zh) |
ES (1) | ES2216635T3 (zh) |
WO (1) | WO2000020388A1 (zh) |
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FR2833489B1 (fr) * | 2001-12-18 | 2004-09-03 | Oreal | Utilisation pour le traitement des cheveux de monomeres electrophiles |
WO2004006878A1 (en) * | 2002-07-10 | 2004-01-22 | Ciba Specialty Chemicals Holding Inc. | Merocyanine derivatives for cosmetic use |
US20040256002A1 (en) * | 2002-07-29 | 2004-12-23 | Tamotsu Horiuchi | Organic dye, photoelectric transducing material, semiconductor electrode, and photoelectric transducing device |
FR2847811B1 (fr) * | 2002-11-29 | 2005-01-07 | Oreal | Composition filtrante contenant au moins un derive du dibenzoylmethane et au moins un derive de 3-(2-azacycloalkylidene)-1,3-dihydro-indol-2-one;procede de photostabilisation |
FR2847813A1 (fr) * | 2002-11-29 | 2004-06-04 | Oreal | Compositions cosmetiques photoprotectrices contenant des derives de 3-(2-azacycloalkylidene)-1,3-dihydro-indol-2-one et utilisations |
US20080260661A1 (en) * | 2004-08-11 | 2008-10-23 | Fuji Photo Film B.V. | Aminobutadiene-Based Uv Screens |
AU2006274968B2 (en) * | 2005-07-29 | 2012-02-23 | Basf Se | Stabilization of body-care and household products against degradation by UV radiation using merocyanine derivatives |
US20070238814A1 (en) * | 2006-04-10 | 2007-10-11 | Basf Corporation | Method of making coating compositions |
GB2445635A (en) * | 2006-10-13 | 2008-07-16 | Ciba Sc Holding Ag | Merocyanine derivatives useful as UV absorbers |
JP5733895B2 (ja) * | 2007-01-25 | 2015-06-10 | チバ ホールディング インコーポレーテッドCiba Holding Inc. | 紫外線感受性有効成分の安定化 |
EP2190404A1 (en) * | 2007-09-18 | 2010-06-02 | Fujifilm Manufacturing Europe B.V. | Uv absorbing compounds |
CN102933195B (zh) | 2010-03-15 | 2015-04-01 | 莱雅公司 | 包含二苯甲酰基甲烷掩蔽剂和部花青二氰基或氰基乙酸酯衍生物的组合物;用于二苯甲酰基甲烷掩蔽剂的光稳定化的方法 |
FR2972346B1 (fr) | 2011-03-09 | 2013-11-08 | Oreal | Utilisation d'un derive diester d'acide 2-methyl succinique comme solvant dans les compositions cosmetiques ; compositions cosmetiques les contenant |
FR2972348B1 (fr) | 2011-03-09 | 2013-03-08 | Oreal | Composition cosmetique contenant un derive de dibenzoylmethane et un compose monoester monoamide d'acide methyl succinique ; procede de photostabilisation |
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GB929394A (en) * | 1958-08-22 | 1963-06-19 | Bayer Ag | Process for dyeing or printing synthetic polymers |
BE790359A (fr) * | 1971-10-23 | 1973-04-20 | Bayer Ag | Procede de teinture de matieres en fibres synthetiques a modification anionique |
US4522808A (en) * | 1980-08-15 | 1985-06-11 | Societe Anonyme Dite: L'oreal | Anti-sunburn compositions containing 2-phenyl-indole derivatives |
US4889410A (en) * | 1988-09-06 | 1989-12-26 | Eastman Kodak Company | Magenta filters |
JP2741782B2 (ja) * | 1989-10-20 | 1998-04-22 | 保土谷化学工業株式会社 | カチオン化合物及びそれを用いる基材の染色法 |
JP3172260B2 (ja) * | 1992-04-30 | 2001-06-04 | 日本コロムビア株式会社 | 光記録媒体 |
DE19539623A1 (de) * | 1995-10-16 | 1997-04-17 | Haarmann & Reimer Gmbh | Sulfonsäuren, Verfahren zu ihrer Herstellung und ihre Verwendung als UV-Absorber |
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1999
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ATE262509T1 (de) | 2004-04-15 |
JP2002526526A (ja) | 2002-08-20 |
KR20010075501A (ko) | 2001-08-09 |
EP1117641A1 (de) | 2001-07-25 |
AU5980399A (en) | 2000-04-26 |
EP1117641B1 (de) | 2004-03-24 |
US6358496B1 (en) | 2002-03-19 |
BR9914255A (pt) | 2001-07-03 |
CN1155569C (zh) | 2004-06-30 |
US6800762B2 (en) | 2004-10-05 |
DE59908967D1 (de) | 2004-04-29 |
US20020103197A1 (en) | 2002-08-01 |
ES2216635T3 (es) | 2004-10-16 |
WO2000020388A1 (de) | 2000-04-13 |
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