CN100349857C - 氨基取代的羟苯基二苯甲酮衍生物 - Google Patents
氨基取代的羟苯基二苯甲酮衍生物 Download PDFInfo
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- CN100349857C CN100349857C CNB2003801058851A CN200380105885A CN100349857C CN 100349857 C CN100349857 C CN 100349857C CN B2003801058851 A CNB2003801058851 A CN B2003801058851A CN 200380105885 A CN200380105885 A CN 200380105885A CN 100349857 C CN100349857 C CN 100349857C
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- PDLPMGPHYARAFP-UHFFFAOYSA-N (3-hydroxy-2-phenylphenyl)-phenylmethanone Chemical class C=1C=CC=CC=1C=1C(O)=CC=CC=1C(=O)C1=CC=CC=C1 PDLPMGPHYARAFP-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 88
- -1 amino substituted hydroxyphenyl benzophenone derivatives Chemical class 0.000 claims abstract description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
- 239000001257 hydrogen Substances 0.000 claims abstract description 26
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims abstract description 14
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims description 79
- 239000003795 chemical substances by application Substances 0.000 claims description 59
- 239000000203 mixture Substances 0.000 claims description 45
- 238000010521 absorption reaction Methods 0.000 claims description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 23
- 125000001118 alkylidene group Chemical group 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 239000006185 dispersion Substances 0.000 claims description 11
- 238000009472 formulation Methods 0.000 claims description 11
- 239000002537 cosmetic Substances 0.000 claims description 10
- 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000005936 piperidyl group Chemical group 0.000 claims description 2
- 239000000516 sunscreening agent Substances 0.000 abstract description 12
- 230000000475 sunscreen effect Effects 0.000 abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 239000004904 UV filter Substances 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 21
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 20
- 238000003756 stirring Methods 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
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- 239000000243 solution Substances 0.000 description 12
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- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 9
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 description 8
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 8
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- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 6
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- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 6
- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 5
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 5
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- 239000001993 wax Substances 0.000 description 5
- JGUMTYWKIBJSTN-UHFFFAOYSA-N 2-ethylhexyl 4-[[4,6-bis[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 JGUMTYWKIBJSTN-UHFFFAOYSA-N 0.000 description 4
- QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 4
- XPJVKCRENWUEJH-UHFFFAOYSA-N Isobutylparaben Chemical compound CC(C)COC(=O)C1=CC=C(O)C=C1 XPJVKCRENWUEJH-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
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- ZFOZVQLOBQUTQQ-UHFFFAOYSA-N Tributyl citrate Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-UHFFFAOYSA-N 0.000 description 4
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
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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 3
- CNXZMGRWEYQCOQ-UHFFFAOYSA-N 2-methoxy-3-phenylprop-2-enoic acid Chemical compound COC(C(O)=O)=CC1=CC=CC=C1 CNXZMGRWEYQCOQ-UHFFFAOYSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- 125000003696 stearoyl group Chemical group O=C([*])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
- 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
- 210000000434 stratum corneum Anatomy 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000012745 toughening agent Substances 0.000 description 1
- 229940098780 tribehenin Drugs 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000008307 w/o/w-emulsion Substances 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
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- 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
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- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
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- 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
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
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- 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
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- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to an acyclic carbon atom of a hydrocarbon radical substituted by oxygen atoms
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- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
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- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/40—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to a carbon atom of a six-membered aromatic ring
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- C07C237/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
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- C07D313/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D313/12—[b,e]-condensed
Abstract
描述了式(1)的氨基取代的羟苯基二苯甲酮衍生物,其中R1和R2彼此独立为:C1-C20烷基;C2-C20链烯基;C3-C10环烷基;C3-C10环烯基;或者R1和R2与相连的氮原子一起形成5-或6-元杂环;n1为1-4的数;当n1=1时,R3为饱和或不饱和杂环基;羟基-C1-C5烷基;任选被一个或多个C1-C5烷基取代的环己基;任选被杂环基、氨基羰基或C1-C5烷基羧基取代的苯基;当n1为2时,R3为任选被羰基或羧基取代的亚烷基、环亚烷基或亚链烯基;或R3与A一起形成式(1a)的二价基团;其中n2为1-3的数;当n1为3时,R3为烷三基;当n1为4时,R3为烷四基;A为-O-;或-N(R5)-;和R5为氢;C1-C5烷基;或羟基-C1-C5烷基。该化合物可在防晒应用中作为UV滤光剂。
Description
本申请涉及氨基取代的羟苯基二苯甲酮衍生物,涉及制备该化合物的方法,该UV吸收剂的用途,优选用于保护人和动物毛发并免受UV辐射损害的用途,以及包括这些化合物的化妆品组合物。
对应于下式的新化合物
R1和R2彼此独立为:C1-C20烷基;C2-C20链烯基;C3-C10环烷基;C3-C10环烯基;或者R1和R2与相连的氮原子一起形成5-或6-元杂环;
n1为1-4的数;
当n1=1时,
R3为饱和或不饱和杂环基;羟基-C1-C5烷基;任选被一个或多个C1-C5烷基取代的环己基;任选被杂环基、氨基羰基或C1-C5烷基羧基取代的苯基;
当n1为2时,
n2为1-3的数;
当n1为3时,
R3为烷三基;
当n1为4时,
R3为烷四基;
A为-O-;或-N(R5)-;和
R5为氢;C1-C5烷基;或羟基-C1-C5烷基。
C1-C20烷基指直链或支链、未取代或取代的烷基,例如,甲基、乙基、丙基、异丙基、正丁基、正己基、环己基、正癸基、正十二烷基、正十八烷基、二十烷基、甲氧基乙基、乙氧基丙基、2-乙基己基、羟乙基、氯丙基、N,N-二乙基氨基丙基、氰基乙基、苯乙基、苄基、对叔丁基苯乙基、对叔辛基苯氧基乙基、3-(2,4-二叔戊基苯氧基)丙基、乙氧基羰基甲基-2-(2-羟基乙氧基)乙基或2-呋喃乙基。
C2-C20链烯基例如为烯丙基、甲代烯丙基、异丙烯基、2-丁烯基、3-丁烯基、异丁烯基、正戊-2,4-二烯基、3-甲基丁-2-烯基、正辛-2-烯基、正十二-2-烯基、异十二烯基、正十二-2-烯基或正十八-4-烯基。
C3-C10环烷基例如为环丙基、环丁基、环戊基、环庚基、环辛基、环壬基或环癸基,并优选环己基。这些基团可被,例如一个或多个相同或不同的C1-C4烷基取代,优选被甲基和/或羟基取代。如果环烷基被一个或多个基团取代,则其优选被一个、两个或四个,并优选被一个或两个相同或不同的基团取代。
C3-C10环烯基例如为环丙烯基、环丁烯基、环戊烯基、环庚烯基、环辛烯基、环壬烯基或环癸烯基,并优选环己烯基。这些基团可被一个或多个相同或不同的C1-C4烷基取代,优选被甲基和/或羟基取代。如果环烯基被一个或多个基团取代,则其优选被一个、两个、三个或四个,并优选被一个或两个相同或不同的基团取代。
羟基取代的C1-C5烷基例如为羟甲基、羟乙基、羟丙基、羟丁基或羟戊基。
亚烷基优选为C1-C12亚烷基,例如亚甲基、亚乙基、亚丙基、亚丁基、亚己基或亚辛基。
亚烷基可任选被一个或多个C1-C5烷基取代。
如果R1和R2为杂环基,则其包括一个、两个、三个或四个相同或不同的环杂原子。特别优选含有一个、两个或三个,特别是一个或两个相同或不同杂原子的杂环。该杂环可为单-或多-环,例如单-、二-或三-环。其优选为单-或二-环,尤其单环。该环优选含有5、6或7个环成员。衍生出式(1)或(2)化合物中出现的基团的单环和二环杂环体系例如为,吡咯、呋喃、噻吩、咪唑、吡唑、1,2,3-三唑、1,2,4-三唑、吡啶、哒嗪、嘧啶、吡嗪、吡喃、噻喃、1,4-二氧己环、1,2-嗪、1,3-嗪、1,4-嗪、吲哚、苯并噻吩、苯并呋喃、吡咯烷、哌啶、哌嗪、吗啉和硫代吗啉。
优选的式(1)化合物为,其中
R1和R2彼此独立为氢;C1-C20烷基;C2-C20链烯基;C3-C10环烷基;C3-C10环烯基;或者R1和R2与相连的氮原子一起形成5-或6-元杂环;
n1为1-4的数;
当n1为1时,
R3为饱和或不饱和杂环基团;羟基-C1-C5烷基;被一个或多个C1-C5烷基取代的环己基;
当n1为2时,
R3为任选被羰基或羧基间隔的亚烷基、环亚烷基或亚链烯基;
当n1为3时,
R3为烷三基;
当n1为4时,
R3为烷四基;
A为-O-;或-N(R5)-;和
R5为氢;C1-C5烷基;或羟基-C1-C5烷基。
优选的有利的式(1)化合物为,其中
R1和R2为C1-C20烷基,优选为C1-C5烷基;最优选为乙基。
优选式(1)中的R1和R2具有相同的定义。
如果式(1)中的n1为1,则优选的化合物为,其中
R3为饱和或不饱和杂环基团,最优选为饱和杂环基团。
这些化合物中,优选的化合物为,其中
R3为具有一个或多个杂原子的5、6或7元单环基团,优选其中
R3为吗啉基;哌嗪基;哌啶基;吡唑烷基;咪唑烷基(imadazolidinyl);或吡咯烷基。
当n1为1时,另外一些式(1)化合物是有利的,其中
R3为不饱和杂环基团,优选为多环基团。
最优选的式(1)化合物为,其中
R5为具有1或2个杂原子的多环杂芳基团。
优选的有利的式(1)化合物为,其中
R6为氢;或C1-C5烷基。
如果n1为2,
则R3优选为C1-C12亚烷基,最优选为C2-C8亚烷基。
最优选的式(1)化合物为,其中
r为0或1;和
q为0-5的数。
如果式(1)中n1为3,
p为0-3的数。
R1、R2和A如式(1)中的定义。
如果式(1)中的n1为4,
R1、R2和A如式(1)中的定义。
R1和R2彼此独立为氢;或者C1-C5烷基;
A为-NH;或-O-;和
R3为饱和或不饱和杂环基。
R1和R2彼此独立为氢;或者C1-C5烷基;
A为-NH;或-O-;和
R3为C1-C12亚烷基。
还优选式(4)的化合物
R1和R2彼此独立为氢;或C1-C5烷基;
A为-NH;或-O-;
p为0-3的数。
此外,还优选式(5)的化合物
R1、R2和A如式(1)中的定义。
本发明的示范化合物为下式的化合物
式(1)的化合物可根据,例如EP-1,046,391中描述的已知方法进行制备。
优选,通过下述方法制备式(1)化合物
(b)使所得酸酐与化合物(4c1)H-N(R4)-R3或H-O-R3反应形成式(1)的化合物
其中
R1和R2彼此独立为氢;C1-C20烷基;C2-C20链烯基;C3-C10环烷基;C3-C10环烯基;或者R1和R2与相连的氮原子一起形成5-或6-元杂环;
n1为1-4;
当n1为1时,
R3为氢;C1-C20烷基;羟基-C1-C5烷基;C2-C20链烯基;未取代或被一个或多个C1-C5烷基取代的C3-C10-环己基;(Y-O)pZ;C6-C10芳基;或饱和或不饱和杂环基;
Y为C1-C12亚烷基;
Z为C1-C5烷基;
p为1-20的数;
如果n1为2,
则R3为任选被羰基或羧基间隔的亚烷基、环亚烷基或亚链烯基;
如果n1为3,
则R3为烷三基;
如果n1为4,
则R3为烷四基;
A为-O-;或-N(R5)-;
R5为氢;C1-C5烷基;或羟基-C1-C5烷基;和
R5为氢;C1-C5烷基;或羟基-C1-C5烷基。
制备方法是本发明的另一个目的。
其中
R1和R2彼此独立为C1-C12烷基;和
R5为氢;C1-C12烷基;或C3-C6环烷基。
反应通常在25-200℃下进行,优选在室温下进行。对于该反应步骤而言,溶剂通常不是必需的。但是,如果使用了溶剂,则工作实施例中所用的溶剂为优选的。
式(1)化合物可容易地重结晶为x-HCl-盐。
式(6b’)的中间体为现有技术中未知的化合物,
R1’和R2”彼此独立为氢;C1-C20烷基;C2-C20链烯基;C3-C10环烷基;C3-C10环烯基;或者R1和R2与相连的氮原子一起形成5-或6-元杂环。
其代表了制备有机UV滤光剂的起始化合物。
式(6b’)化合物为本发明的又一个目的。
式(1)化合物特别适于作为UV滤光剂,也就是说适于用来保护对紫外线敏感的有机材料,尤其是保护任何动物的皮肤和毛发,以防止UV辐射作用。因此,这种化合物也适于作为化妆品、药物学和兽医学制剂中的防晒试剂。
因此,本发明的又一个目的是化妆品制剂,其包括至少一种式(1)的化合物和化妆品可接受的载体或添加剂。
根据本发明的UV吸收剂可作为溶解状态(可溶的有机滤光剂、溶解的有机滤光剂)或作为微粉状态(纳米数量级的有机滤光剂、颗粒状有机滤光剂、UV-吸收剂颜料)来使用。
任何已知的适于制备微粒的方法都可用于制备微粉化的UV吸收剂,例如:
-湿磨法(形成可泵送分散体的低-粘度微粉化方法),在球磨机中使用硬磨介质,例如硅酸锆球,以及存在于水中或适当有机溶剂中的保护性表面活性剂或保护性聚合物;
-使用连续或非连续(间歇)捏合机的湿式-混合法(形成非-泵送浆料的高粘度微粉化方法)。对于湿式-混合法,可使用溶剂(水或化妆品中可接受的油)、助磨剂(表面活性剂、乳化剂)和聚合助磨剂。
两种方法都可优选使用。
-从适当的溶剂中进行喷雾-干燥的方法,例如从水悬浮液或含有有机溶剂的悬浮液,或水、乙醇、二氯乙烷、甲苯或N-甲基吡咯烷酮等中的真溶液。
-根据RESS方法(超临界溶液的迅速膨胀(
Rapid
Expansion ofSupercritical
Solutions))使溶解了一种或多种UV滤光剂的超临界流体(如,CO2)进行膨胀,或者使液体二氧化碳与由一种或多种UV滤光剂溶于适当有机溶剂而形成的溶液一起膨胀;
-从适当溶剂中再沉淀,该溶剂包括超临界流体(GASR方法=气相逆-溶剂重结晶法(
Gas
Anti-
Solvent
Recrystallisation)/PCA方法=使用压缩逆-溶剂的沉淀法(
Precipitation with
CompressedAnti-Solvents))。
作为制备微粉化有机UV吸收剂的研磨装置,可使用,例如喷射磨机、球磨机、振动磨机或锤磨机,优选高速混砂机。更优选的磨机为新型球磨机;这些类型磨机的制造商例如为,Netzsch(LMZ磨机)、Drais(DCP-Viscoflow或Cosmo)、Bühler AG(离心式磨机)或Bachhofer。碾磨中优选使用助磨剂。
用于制备微粉化有机UV吸收剂的捏合机装置的例子为典型的西格马-叶片式分批捏合机,还有串联的分批捏合机(IKA-Werke)或连续捏合机(产自Werner和Pfleiderer的Continua)。
适用于上述所有微粉化方法的低分子量助磨剂为分散剂、表面活性剂和乳化剂,其在下面题目为“乳化剂”、“表面活性剂”和“脂肪醇”的部分中进行了描述。
适用于水分散体的聚合助磨剂为化妆品中可接受的Mn>500g/mol的水溶性聚合物,例如:丙烯酸酯(Salcare型)、改性或未改性的多糖、多聚葡萄糖或黄原胶。此外,还可使用烷基化的乙烯基-吡咯烷酮聚合物、乙烯基吡咯烷酮/醋酸乙烯酯共聚物、酰基谷氨酸、烷基多聚葡萄糖、Ceteareth-25或磷脂。油分散体可包括化妆品可接受的蜡状聚合物或天然蜡,其作为聚合助磨剂在加工过程中和之后调节粘度。其它可用的助磨剂的例子在下面题目为“聚合物”的部分中进行了公开。
可用的溶剂为水、盐水、(聚-)乙二醇、甘油或化妆品可接受的油。其它可用的溶剂在下面题目为“脂肪酸酯”、“天然和合成甘油三酯,包括甘油酯和衍生物”、“珠光蜡”、“烃油”和“硅酮或硅氧烷”的部分中进行了公开。
如此得到的微粉化UV吸收剂通常具有0.02-2微米的平均粒度,优选为0.03-1.5微米,更优选为0.05-1.0微米。
本发明的另一个目的是UV吸收剂分散体,其包括
(a)式(1’)的微粉化UV吸收剂
其中
R1和R2彼此独立为氢;C1-C20烷基;C2-C20链烯基;C3-C10环烷基;C3-C10环烯基;或者R1和R2与相连的氮原子一起形成5-或6-元杂环;
当n1为1时,
R3为氢;C1-C20烷基;羟基-C1-C5烷基;C2-C20链烯基;未取代或被一个或多个C1-C5烷基取代的C3-C10环己基;(Y-O)pZ;C6-C10芳基;或者饱和或不饱和杂环基;
Y为C1-C12亚烷基;
Z为C1-C5烷基;
p为1-20的数;
当n1为2时,
R3为任选被羰基或羧基间隔的亚烷基、环亚烷基或亚链烯基;
如果n1为3,
则R3为烷三基;
如果n1为4,
则R3为烷四基;
A为-O-;或-N(R5)-;和
R5为氢;C1-C5烷基;或羟基-C1-C5烷基;
R5为氢;C1-C5烷基;或羟基-C1-C5烷基;
其粒度为0.02-2μm,和
(b)适当的分散剂。
根据本发明的UV吸收剂还可以使用其干燥粉末形式。为此,要用已知的碾磨方法对UV吸收剂进行碾磨,例如用真空粉化、逆流喷雾干燥法等。这种粉末的粒度为0.1微米-2微米。为了避免发生团聚作用,可在粉碎步骤之前使用表面-活性的化合物涂覆在UV吸收剂上,例如使用阴离子、非离子或两性表面活性剂,如磷脂或已知聚合物,例如PVP、丙烯酸酯等表面活性剂。
根据本发明的UV吸收剂还可用在特殊的化妆品载体中,例如用在固体类脂纳米粒子(SLN)中,或用在惰性溶胶凝胶微胶囊中,而UV吸收剂被封在该胶囊中。
根据本发明的化妆品制剂或药物组合物还可包括一种或多种另外的UV滤光剂。
可使用传统方法物理混合UV吸收剂和添加剂,从而制备化妆品或药物制剂,例如,通过将单独组分简单搅拌在一起进行制备,尤其是利用已知的化妆品UV吸收剂,例如,甲氧基肉桂酸辛酯、水杨酸异辛酯等的溶解性质来制备。UV吸收剂可,例如,无需进一步处理,或以微粉化状态或粉末形式使用。
化妆品和药物制剂含有基于组合物总重的0.05%-40%重的一种UV吸收剂或UV吸收剂的混合物。
优选,根据本发明的式(1)UV吸收剂与任选的其它防光照试剂之间的重量混合比为1∶99-99∶1,尤其为1∶95-95∶1,优选10∶90-90∶10。特别有利的是混合比为20∶80-80∶20,尤其是40∶60-60∶40,且优选为约50∶50。这种混合物可特别用于改善溶解性或提高UV吸收性。
根据本发明的式(1)UV吸收剂或UV滤光剂的组合适用于保护皮肤、毛发和/或天然或人造发色。
可与本发明的UV吸收剂一起使用的适当的其它UV滤光物质为任意的UV-A和UV-B滤光物质。
化妆品或药物制剂可为,例如,乳剂、凝胶、洗剂、醇和水/醇溶液、乳液、蜡/脂肪组合物、条状制剂、粉末或软膏。除上述UV滤光剂之外,化妆品或药物制剂还可含有下列添加剂。
作为含水和含油的乳液(如,W/O、O/W、O/W/O和W/O/W乳液或微乳),该制剂可含有,例如,基于组合物总重的,0.1-30%重,优选0.1-15%重,特别是0.5-10%重的一种或多种UV吸收剂,含有基于组合物总重的,1-60%重,特别是5-50%重,且优选10-35%重的至少一种油组分,含有基于组合物总重的,0-30%重,特别是1-30%重,且优选4-20%重的至少一种乳化剂,含有基于组合物总重的,10-90%重,尤其是30-90%重的水,和含有基于组合物总重的,0-88.9%重,尤其是1-50%重的化妆品可接受的其它添加剂。
根据本发明的化妆品或药物组合物/制剂还可含有一种或多种下述的附加化合物,例如,脂肪醇、脂肪酸酯、天然或合成甘油三酯,其包括甘油酯和衍生物、珠光蜡、烃油、硅酮或硅氧烷(有机官能团-取代的聚硅氧烷)、氟化或全氟油、乳化剂、助剂和添加剂、富脂剂、表面活性剂、稠度调节剂/增稠剂和流变性调节剂、聚合物、抗皮屑试剂、成膜剂、抗氧化剂、亲水剂、防腐剂和抑菌剂、芳香油、着色剂或作为SPF增强剂的聚合物球或空心球体。
化妆品或药物制剂
在许多种化妆品制剂中都含有化妆品或药物制剂。比较重要的,例如,尤其是下列制剂:
-护肤制剂,例如,片剂形式或液体皂形式的皮肤-洗涤和清理制剂、无肥皂的洗涤剂或洗涤膏;
-洗浴制剂,例如,液体(泡沫浴剂、乳剂、淋浴制剂)或固体浴剂、例如洗浴方块和洗浴盐;
-护肤制剂,例如,润肤乳,多用乳剂或护肤油;
-化妆品个人护理制剂,例如,日霜或粉霜形式的面部化妆品、扑面粉(散装或压制的)、胭脂或乳液化妆品,眼部护理制剂,如眼影制剂、染睫毛油、眼线、眼霜或眼部定型乳;唇部护理制剂,如口红、润唇膏、唇线笔,指甲护理制剂,例如,指甲油、洗甲剂、指甲硬化剂或角质层除去剂;
-足部护理制剂,例如,足浴剂、足粉、足膏或足部香膏、特种除臭剂和止汗剂或除茧制剂;
-防光照制剂,例如,防光照乳液、洗液、霜或油、防晒霜或防酷热剂、防晒黑制剂,或晒后修复制剂;
-使皮肤变成褐色的制剂,例如,自变褐乳膏;
-除色素制剂,例如,用于漂白皮肤的制剂或使皮肤具有光泽的制剂;
-除虫剂,例如,除虫油、洗液、喷雾或棒;
-除臭剂,例如除臭喷雾、泵送喷雾、除臭胶、棒或滚条;
-止汗药,例如抗发汗棒,乳膏或滚条;
-用于清洁和护理有瑕疵的皮肤的制剂,例如,合成洗涤剂(固体或液体)、去皮或擦洗制剂或去皮面膜;
-化学形式的脱毛发制剂(脱毛),例如,脱毛粉、液体脱毛制剂、膏或糊状脱毛制剂、凝胶或气溶胶形式的制剂;
-剃须制剂,例如,剃须皂、泡沫剃须膏、非泡沫剃须膏、泡沫体和凝胶、用于干式剃须的剃前制剂、剃后洗剂或洗液;
-香味制剂,例如,香料(eau de Cologne、eau de toilette、eau de parfum、parfum de toilette、香水)、芳香油或芳香膏;
-美容用的毛发处理制剂,例如,洗发香波和调节剂形式的洗发制剂,护发制剂,例如,预处理制剂、头发滋补剂、定型膏、定型胶、润发油、头发漂洗剂、处理套装、密发处理剂,头发定型化制剂,例如,烫成持久波浪的波浪烫发制剂(热波浪、温和波浪、冷波浪)、直发制剂、液体固发制剂、发泡沫剂、头发定型剂,漂白剂,如过氧化氢溶液、亮泽洗发香波、漂白膏、漂白粉、漂白浆或油、临时、半持久或持久染发剂、含有自氧化染料的制剂,或天然染发剂,例如指甲花染料或甘菊染料。
外观形式
列出的最终剂型可为各种外观形式,例如:
-液体制剂形式,如W/O、O/W、O/W/O、W/O/W或PIT乳剂和各种的微乳,
-凝胶形式,
-油、膏、奶或洗液的形式,
-粉末、漆、片剂或化妆用品形式,
-条棒形式,
-喷雾(用推进气或泵送喷洒来喷射)或气溶胶形式,
-泡沫形式,或
-糊浆形式。
特别重要的皮肤美容制剂为防光照制剂,例如防光照乳、洗液、膏、油、防晒霜或防酷热剂、防晒黑制剂或晒后修复制剂,还有使皮肤成褐色的制剂,例如自变褐乳膏。特别有用的是防晒膏、防晒液、防晒乳和喷雾形式的防晒制剂。
特别重要的头发美容制剂为上述头发处理制剂,尤其是洗发香波形式的洗发制剂、头发调理剂、护发制剂,如预处理制剂、头发滋补剂、定型膏、定型胶、润发油、头发漂洗剂、处理套装、密发处理剂,直发制剂、液体固发制剂、发泡沫剂和头发定型剂。特别有用的是洗发香波形式的洗发剂。
洗发香波具有,例如,下列组成:0.01-5%重的本发明的UV吸收剂、12.0%重的月桂基-2-硫酸钠、4.0%重的椰油酰胺基丙基甜菜碱、3.0%重的氯化钠和添加水至100%。
例如,尤其可使用下列头发美容制剂:
a1)由根据本发明的UV吸收剂、PEG-6-C10氧代醇和脱水山梨糖醇倍半油酸酯组成的自发乳化原料制剂,并向其中加入水和任何希望的季铵盐化合物,例如4%的貂油酰胺基(minkamido)丙基二甲基-2-羟乙基氯化铵或Quaternium 80;
a2)由根据本发明的UV吸收剂、柠檬酸三丁酯和PEG-20-单油酸山梨糖醇酯组成的自发乳化原料制剂,并向其中加入水和任何希望的季铵盐化合物,例如4%的貂油酰胺基丙基二甲基-2-羟乙基氯化铵或Quaternium 80:
b)根据本发明的UV吸收剂在丁基三甘醇醚和柠檬酸三丁酯中形成的四部分-掺杂的(quat-doped)溶液;
c)根据本发明的UV吸收剂与正烷基吡咯烷酮的混合物或形成的溶液。
该制剂中常用的其它成分为防腐剂、杀菌剂和抑菌剂、香料、染料、颜料、增稠剂、加湿剂、湿润剂、脂肪、油、蜡或其它化妆品和个人护理制剂的常用成分,例如醇、多元醇、聚合物、电解质、有机溶剂、硅衍生物、软化剂、乳化剂或乳化表面活性剂、表面活性剂、分散剂、抗氧化剂、抗刺激试剂和抗炎试剂等。
新化合物的制备
实施例1:3-二乙基氨基双苯并-庚英(DEDO)的制备
在室温的反应釜中,边搅拌边将62.7g式(101a)的化合物
悬浮在400g乙酸乙酯中。将溶解在200g乙酸乙酯中的44.4g二环己基碳二亚胺溶液混合至该悬浮液中。温度升高至约30℃。室温下,在约10小时的过程中剧烈搅拌该悬浮液,之后进行过滤。蒸发后,从乙酸乙酯(60g)/环己烷(220g)混合物中重结晶得到式(101)的纯产物,其为黄色晶体。
产量:42g
Fp:83.5℃
分析:C、H、N含量与理论值一致;H-NMR;C-NMR;MS确定了庚英结构。
采用类似步骤,用乙酸酐代替二环己基碳二亚胺与BB-酸进行脱水反应(dehydratisation)可获得化合物。
实施例2:式(102)化合物的制备
室温下,将7.2g 2-(4-氨基苯基)-6-甲基苯并噻唑悬浮在60ml二乙二醇二甲醚中。搅拌下向其中加入10.6g式(101)化合物溶解在20ml二乙二醇二甲醚中形成的溶液,并将反应物质加热至90℃。反应4小时后,将反应物质冷却至室温并过滤出粗产物。用乙醇萃取粗产物得到纯化合物。
产量:7.3g米色粉末
Fp:225℃
C=71.6%;H=5.2%;N=7.8%;S=5.96%
所有值都与理论值一致。
在二氧己环中的UV谱图:
1.最大值在336nm e=57318
2.最大值在360nm e=49032
实施例3:活性成分含量为38%分散体的制备:
在装有19.3g 0.3-0.4mm研磨珠ER120S的Dispermat LC中,将
3.4g式(102)化合物
0.3g Arlacel P 135,和
5.3g Crodamol AB
研磨4.5小时。得到非常精细研磨的分散体,其SPF值为16.4。
该分散体具有非常好的宽UV-范围(320-380nm)。
实施例4:式(103)化合物的制备
将6g式(101)化合物溶解在40ml二氧己环中。边搅拌边向该溶液中加入2.5g 4-氨基苯甲酰胺。85℃下反应2小时后真空除去二氧己环,剩余物经处理从2-甲氧基乙醇中重结晶出来形成纯产物。
产量:3g白色晶体
Fp:254℃
元素分析:C、H、N含量与理论值一致。
在二氧己环中的UV谱图:
最大值在358nm;e=34848。
实施例5:式(104)化合物的制备
110℃下,将2.36g 1,6-己二醇、6g甲苯和11.8g式(101)化合物搅拌5小时。
之后蒸馏出甲苯,而馏出的剩余物从丙酮中重结晶出来。
产量:7.2g白色晶体
Fp:148℃
实施例6:式(105)化合物的制备
100℃下,将9.2g式(101)化合物、14.4g薄荷醇的外消旋混合物、18ml二乙二醇二甲醚、0.1g 1.8-二氮杂二环(5.4.0)-十一碳-7-烯(1,5,5)搅拌2小时。然后在真空下除去溶剂,并用柱色谱法(Kieselgel 60/甲苯-乙酸酯8∶2)分离剩余物。
产量:12.8g玻璃质的非晶体物质
分析:C/H/N=74.5%/8.4%/3.04%,与理论值一致。
在二氧己环中的UV谱图:
最大值在351nm;e=38565。
实施例7:式(106)化合物的制备
室温下将6g式(101)化合物溶解在30ml二氧己环中。搅拌下将溶解在20ml二氧己环中的1.16g 1,6-二氨基己烷加入到该溶液中。室温下持续搅拌该反应物质12小时,然后在真空下除去二氧己环,用水萃取后从甲醇中重结晶得到粗产物。
产量:4.2g,黄色晶体
Fp:160℃
元素分析与理论值一致。
实施例8:式(107)化合物的制备
将9g式(101)化合物和8.4g苯胺溶解在18ml二乙二醇二甲醚中。将反应保温至70℃,并在此温度下搅拌3小时。经真空蒸发反应物质后,从甲醇中重结晶得到纯产物。
产量:6.2g黄色晶体
Fp:152℃。
UV谱图(在二氧己环中)
最大值在359nm;e=34724。
实施例9:式(108)化合物的制备
将7.4g式(101)化合物溶解在25ml二氧己环中。将溶解在10ml二氧己环中的3.3g吗啉搅拌加入到该溶液中。室温下搅拌反应物质约20小时,真空蒸发反应混合物,纯产物从乙酸乙酯中重结晶出来。
产量:7.5g黄色晶体;
Fp:155℃
UV谱图(在二氧己环中):
最大值在360nm;e=37900。
实施例10:式(109)化合物的制备
将9g式(101)化合物、9.5g二乙醇胺溶解在30ml二乙二醇二甲醚中,并在85℃下搅拌3小时。真空浓缩反应物质(0.03mB/70℃)。剩余物在70℃下用约250ml水萃取。冷却后纯产物从水相中重结晶出来。
产量:2.1g黄色晶体;
Fp:141℃
UV谱图(在二氧己环中)
最大值在359nm;e=35080。
实施例11:式(110)化合物的制备
室温下,将下列物质剧烈搅拌16小时
125.2g 4-二乙氨基-2-羟基二苯甲酮碳素酸(BB-酸)
700ml乙酸乙酯,
38.8g碳酸钾;和
53.1g乙酸酐。
过滤反应混合物,将滤液蒸发至157g。脱水形式的BB-酸(DEDO)从蒸发的剩余物中重结晶出来
产量:99g(黄色晶体;Fp=82℃)
将晶体溶解在18g二乙二醇二甲醚中,110℃下,边搅拌边将14.6g2-丁烯-1,4-二醇和1.1g 4-二甲氨基吡啶加入到二酯(式(101)化合物)中。
得到了定量的产量。
通过柱色谱法得到纯化合物-Kieselgel 60/洗脱剂∶甲苯乙酸乙酯/8∶2。
碎片形式的纯产物为无定形黄色粉末。
其具有良好的溶解性,例如,在Finsolve TN(C12-15苯甲酸烷基酯)中>10%。
在二氧己环中的UV-谱图:最大值在351nm;摩尔Ext.为65551。
实施例12:式(111)化合物的制备
类似实施例11,用2,2-二甲基-1,3-丙二醇代替2-丁烯-1,4-二醇与无水形式的BB-酸反应。
可根据上述方法逐步生产出粗产物。
所得化合物为无定形的黄色粉末
在Finsolve TN中的溶解性>30%
在乙醇中的UV谱图:最大值为354nm,摩尔消光系数为65296。
实施例13-23:其它羟基苯基二苯甲酮衍生物的制备
根据实施例11中所述的方法制得下列化合物:
应用实施例
实施例24:防晒剂的制备
Sinnowax AoCerasynt SD-V十六醇Dow Corning 200流体Witconol TN式(110)的化合物辛基三嗪酮丁基甲氧基二苯甲酰基甲烷甘油EDTA | 7g2g1.5g1g15g2g2g1.5g10g0.2g |
防腐剂/去离子水 | 补充至100g |
实施例25:防晒制剂的制备
SINNOWAX AOCerasynt SD-V十六醇Dow Corning 200流体witconolWitconol TN辛基三嗪酮丁基甲氧基二苯甲酰基甲烷Parsol 1789(Hoffman-La Roche)甘油式(111)的化合物 | 7g2g1.5g1g15g2g2g1.5g10g2g |
防腐剂/去离子水 | 补充至100g |
实施例26:防晒制剂的制备
Arlacel 165 FL硬脂酰醇甘油三硬脂酸酯 TPDow Corning 20O流体Witconol TN三乙醇胺式(111)的化合物辛基三嗪酮丁基甲氧基二苯甲酰基甲烷甘油Amphisol KSynhal en K甲基纤维素F4M EDTA三乙醇胺防腐剂/去离子水 | 2g1g2.5g0.5g15g0.5g1.5g2g1g5g1g0.3g0.1g0.2gauf pH=7补充至100g |
实施例27:O/W乳液
(A):
式(110)或(111)的化合物 3g
芝麻油 10g
硬脂酸甘油酯 4g
硬脂酸 1g
十六烷醇 0.5g
聚山梨醇酯 0.2g
(B):
丙二醇 4g
对羟苯甲酸丙酯 0.05g
对羟苯甲酸甲酯 0.15g
三乙醇胺 0.1g
卡波姆934 0.1g
水 补充至100ml
乳剂的制备
阶段(A):
首先,将UV吸收剂溶解在芝麻油中。将(A)的其它组分加入其中并混合。
阶段(B):
将对羟苯甲酸丙酯和对羟苯甲酸甲酯溶解在丙二醇中。之后加入60ml水,加热至70℃,然后在其中乳化卡波姆934。
乳剂:
在剧烈的机械搅拌下将(A)缓慢加入到(B)中。加入水将体积调节至100ml。
实施例28:日常护理霜,O/W型
INCI名称 %w/w
(所用的)
部分A 硬脂酸甘油酯(和)鲸蜡硬脂醇(和)棕榈 4.0
酸十六醇酯(和)椰油甘油酯
Ceteareth-12 4.0
鲸蜡硬脂醇 2.0
二辛酰基醚 4.5
硬脂酸乙基己基酯 4.0
月桂酸己酯 3.5
乙基己基三嗪酮 1.0
苯亚甲基丙二酸酯聚硅氧烷 2.0
HDI/三羟甲基己基-内酯交联聚合物(和) 5.0
二氧化硅
十八烷基二甲聚硅氧烷 1.0
二甲聚硅氧烷 2.0
鲸蜡醇 0.8
式(110)或(111)的化合物 2.0
部分B 水 适量添加至100
水(和)硬葡聚糖(和)苯氧乙醇 2.0
甘油 2.0
部分C Steareth-10烯丙基醚/丙烯酸酯共聚物 0.45
苯氧乙醇(和)对羟苯甲酸甲酯(和)对羟 0.7
苯甲酸乙酯(和)对羟苯甲酸丁酯(和)对
羟苯甲酸丙酯(和)对羟苯甲酸异丁酯
部分D 水(和)生育酚乙酸酯(和)辛酸/癸酸甘 4.0
油三酯(和)聚山梨醇酯80(和)卵磷脂
部分E 水(和)氢氧化钠 适量
香料 适量
制备步骤:
将部分A和部分B分别加热至80℃。将部分A倾入部分B中,同时连续搅拌。之后用Ultra Turrax在11000rpm下将混合物均匀化20秒。将混合物冷却至60℃并加入部分C。在低于30℃的温度下,加入部分D并用氢氧化钠将pH调节至6.5-7.0。最后,加入香料。实施例29:防晒霜,O/W型
INCI名称 %w/w
(所用的)
部分A 聚甘油基-3甲基葡萄糖二硬脂酸酯 2.0
油酸癸酯 5.7
棕榈酸异丙酯 5.8
辛酸/癸酸甘油三酯 6.5
式(110)或(111)的化合物 2.0
甲氧基肉桂酸乙基己基酯 5.0
鲸蜡醇 0.7
部分B 甘油 3.0
卡波姆 0.3
水 适量添加至100
部分C 苯氧乙醇(和)对羟苯甲酸甲酯(和)对羟 0.5
苯甲酸乙酯(和)对羟苯甲酸丁酯(和)对
羟苯甲酸丙酯(和)对羟苯甲酸异丁酯
部分D 2,2’-亚甲基-双-(6-(2H-苯并三唑-2- 8.0
基)-4-(1,1,3,3-四甲基丁基)苯酚
(Tinosorb M)(和)水(和)癸基葡糖
苷(和)丙二醇(和)黄原胶
水 20.0
部分E 水(和)氢氧化钠 适量
香料 适量
制备步骤:
将部分A和部分B分别加热至75℃。将部分A倾入部分B中,同时搅拌。用Ultra Turrax在11000rpm下将混合物均匀化15秒。将混合物冷却至60℃并与部分C和部分D混合。在短时间内(5秒/11000rpm)再次对混合物进行均匀化,同时适度搅拌。在室温下用氢氧化钠将pH调节至5.5-6.0。最后,加入香料。
实施例30:防UV日常护理洗液
INCI名称 %w/w
(所用的)
部分A Oleth-3磷酸酯 0.6
Steareth-21 2.5
Steareth-2 1.0
鲸蜡醇 0.8
硬脂醇 1.5
Tribehenin 0.8
异鲸蜡烷 8.0
式(110)或(111)的化合物 2.0
部分B 水 适量添加至100
甘油 2.0
2,2’-亚甲基-双-(6-(2H-苯并三唑-2- 3.0
基)-4-(1,1,3,3-四甲基丁基)苯酚
(Tinosorb M)(和)水(和)癸基葡糖
苷(和)丙二醇(和)黄原胶
EDTA二钠盐 0.1
部分C 水 20.0
二唑烷基脲(和)碘代丙炔基丁基氨基甲酸酯 0.15
丙二醇 4.0
部分D 丙烯酸钠共聚物(和)液体石蜡(和)PPG-1 1.5
trideceth-6
环戊二烯并硅氧烷 4.5
PEG-12二甲聚硅氧烷 2.0
生育酚乙酸酯 0.45
水(和)柠檬酸 适量
部分E 香料 适量
制备步骤:
将部分A和部分B分别加热至75℃。将部分A倾入部分B中,同时连续搅拌。乳化后马上与部分D的SF 1202和SF 1288混合起来。用Ultra Turrax在11000rpm下将混合物均匀化30秒。使混合物冷却至65℃并与SALCARESC91混合。在低于50℃的温度下加入部分C。在35℃或更低温度下混合入维生素E乙酸酯,随后用柠檬酸调节pH。室温下加入部分E。
实施例31:防晒霜,O/W型
INCI名称 %w/w
(所用的)
部分A 聚甘油基-3甲基葡萄糖二硬脂酸酯 2.0
油酸癸酯 5.7
棕榈酸异丙酯 5.8
辛酸/癸酸甘油三酯 6.5
式(110)或(111)的化合物 2.0
甲氧基肉桂酸乙基己基酯 5.0
鲸蜡醇 0.7
部分B 甘油 3.0
卡波姆 0.3
水 适量添加至100
部分C 苯氧乙醇(和)对羟苯甲酸甲酯(和)对羟 0.5
苯甲酸乙酯(和)对羟苯甲酸丁酯(和)对
羟苯甲酸丙酯(和)对羟苯甲酸异丁酯
部分D 2,2’-亚甲基-双-(6-(2H-苯并三唑-2- 8.0
基)-4-(1,1,3,3-四甲基丁基)苯酚(和)
水(和)癸基葡糖苷(和)丙二醇(和)黄
原胶
水 20.0
部分E 水(和)氢氧化钠 适量
香料 适量
制备步骤:
将部分A和部分B分别加热至75℃。将部分A倾入部分B中,同时搅拌。用11000rpm的Ultra Turrax使混合物均匀化15秒。将混合物冷却至60℃并与部分C和部分D混合。在短时间内(5秒/11000rpm)再次对混合物进行均匀化。进一步冷却后,在室温下用氢氧化钠调节pH,并适度搅拌。获得pH为5.50-6.00的溶液。最后,加入香料。
实施例32:防晒霜,O/W型
INCI名称 %w/w
(所用的)
部分A 聚甘油基-3甲基葡萄糖二硬脂酸酯 2.0
油酸癸酯 5.7
棕榈酸异丙酯 5.8
辛酸/癸酸甘油三酯 6.5
式(110)或(111)化合物(50%)与Uvinul 2.0
A加CAS登记号302776-68-7(50%)
甲氧基肉桂酸乙基己基酯 5.0
鲸蜡醇 0.7
部分B 甘油 3.0
卡波姆 0.3
水 适量添加至100
部分C 苯氧乙醇(和)对羟苯甲酸甲酯(和)对羟 0.5
苯甲酸乙酯(和)对羟苯甲酸丁酯(和)对
羟苯甲酸丙酯(和)对羟苯甲酸异丁酯
部分D 2,2’-亚甲基-双-(6-(2H-苯并三唑-2- 8.0
基)-4-(1,1,3,3-四甲基丁基)苯酚(和)
水(和)癸基葡糖苷(和)丙二醇(和)黄
原胶
水 20.0
部分E 水(和)氢氧化钠 适量
香料 适量
制备步骤:
将部分A和部分B分别加热至75℃。将部分A倾入部分B中,同时搅拌。使用Ulira Turrax,在11000rpm下对混合物均匀化15秒。冷却至60℃后,混入部分C和部分D。在短时间内(5秒/11000rpm)再次对混合物均匀化。进一步冷却后,在室温下并适度搅拌下用氢氧化钠溶液将pH调节至5.50-6.00。最后,加入香料。
Claims (16)
2.根据权利要求1的化合物,其中
R1和R2彼此独立为氢;C1-C20烷基;C2-C20链烯基;C3-C10环烷基;C3-C10环烯基;或者R1和R2与相连的氮原子一起形成5-或6-元杂环;
n1为1或2;
当n1为1时,
R3为饱和或不饱和杂环基团;
当n1为2时,
R3为任选被羰基或羧基间隔的亚烷基、亚环烷基或亚链烯基。
3.根据权利要求1或2的化合物,其中
R1和R2为C1-C20烷基。
4.根据权利要求1的化合物,其中
R1和R2彼此独立为C1-C5烷基。
5.根据权利要求1的化合物,其中
式(1)中的R1和R2具有相同的定义。
6.根据权利要求1的化合物,其中
R3为具有一个或多个杂原子的5、6或7元单环基团。
7.根据权利要求6的化合物,其中
R3为吗啉基;哌嗪基;哌啶基;吡唑烷基;咪唑烷基;或吡咯烷基。
8.根据权利要求1的化合物,其中
如果n1为2,
则R3为C1-C12亚烷基,且
R1、R2和A如权利要求1中的定义。
12.一种制备式(1)化合物的方法,其包括
(b)使该酸酐与化合物(6c1)H-N(R5)-R3或(6c2)H-O-R3反应形成式(1’)的化合物
R1和R2与相连的氮原子一起形成5-或6-元杂环;
n1为1或2;
如果n1为1,
则R3为氢;C1-C20烷基;羟基-C1-C5烷基;C2-C20链烯基;未取代或被一个或多个C1-C5烷基取代的环己基;(Y-O)pZ;C6-C10芳基;或饱和或不饱和杂环基;
Y为C1-C12亚烷基;
Z为C1-C5烷基;
p为1-20的数;
如果n1为2,
则R3为任选被羰基或羧基间隔的亚烷基、环亚烷基或亚链烯基。
13.式(1)化合物用于保护人和动物毛发和皮肤免受UV辐射的用途。
14.根据权利要求13的用途,其中式(1)化合物以微粉化形式存在。
15.一种化妆品制剂,包括至少一种或多种根据权利要求1的式(1)化合物,和化妆品可接受的载体或添加剂。
16.UV-吸收剂-分散体,其包括
(a)式(1’)的微粉化UV吸收剂
R1和R2彼此独立为氢;C1-C20烷基;C2-C20链烯基;C3-C10环烷基;C3-C10环烯基;或者R1和R2与相连的氮原子一起形成5-或6-元杂环;
n1为1或2,
当n1为1时,
R3为氢;C1-C20烷基;羟基-C1-C5烷基;C2-C20链烯基;未取代或被一个或多个C1-C5烷基取代的环己基;(Y-O)pZ;C6-C10芳基;或者饱和或不饱和杂环基;
Y为C1-C12亚烷基;
Z为C1-C5烷基;
p为1-20的数;
当n1为2时,
R3为任选被羰基或羧基间隔的亚烷基、环亚烷基或亚链烯基;
和
(b)适当的分散剂。
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GB2433439A (en) | 2005-12-21 | 2007-06-27 | Ciba Sc Holding Ag | Use of transmission dyes to protect human skin from UV radiation |
JP5294877B2 (ja) * | 2006-02-09 | 2013-09-18 | チバ ホールディング インコーポレーテッド | ヒドロキシベンゾフェノン誘導体 |
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FR2833164B1 (fr) * | 2001-12-07 | 2004-07-16 | Oreal | Compositions cosmetiques antisolaires a base d'un melange synergique de filtres et utilisations |
JP2015098471A (ja) * | 2013-11-18 | 2015-05-28 | 東洋合成工業株式会社 | 化学種発生向上試剤 |
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- 2003-12-03 MX MXPA05006197 patent/MX271169B/es active IP Right Grant
- 2003-12-03 ES ES03796081T patent/ES2381872T3/es not_active Expired - Lifetime
- 2003-12-03 AU AU2003298343A patent/AU2003298343B2/en not_active Ceased
- 2003-12-03 BR BRPI0316607-4A patent/BR0316607B1/pt active IP Right Grant
- 2003-12-03 AT AT03796081T patent/ATE553076T1/de active
- 2003-12-03 KR KR1020057010430A patent/KR101057747B1/ko active IP Right Grant
- 2003-12-03 JP JP2005502323A patent/JP4566907B2/ja not_active Expired - Fee Related
- 2003-12-03 CN CNB2003801058851A patent/CN100349857C/zh not_active Expired - Lifetime
- 2003-12-03 WO PCT/EP2003/050937 patent/WO2004052837A2/en active Application Filing
- 2003-12-03 US US10/537,940 patent/US7374749B2/en not_active Expired - Lifetime
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EP1046391A2 (de) * | 1999-04-20 | 2000-10-25 | Basf Aktiengesellschaft | Verwendung von aminosubstituierten Hydroxybenzophenonen als photostabile UV-Filter in kosmetischen und pharmazeutischen Zubereitungen |
Also Published As
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AU2003298343B2 (en) | 2010-02-25 |
JP4566907B2 (ja) | 2010-10-20 |
ES2381872T3 (es) | 2012-06-01 |
JP2006509834A (ja) | 2006-03-23 |
KR101057747B1 (ko) | 2011-08-19 |
WO2004052837A2 (en) | 2004-06-24 |
AU2003298343A1 (en) | 2004-06-30 |
CN1726184A (zh) | 2006-01-25 |
US20060018846A1 (en) | 2006-01-26 |
EP1569893A2 (en) | 2005-09-07 |
KR20050085469A (ko) | 2005-08-29 |
BR0316607B1 (pt) | 2014-12-23 |
MX271169B (es) | 2009-10-23 |
ATE553076T1 (de) | 2012-04-15 |
WO2004052837A3 (en) | 2004-09-10 |
EP1569893B1 (en) | 2012-04-11 |
US7374749B2 (en) | 2008-05-20 |
BR0316607A (pt) | 2005-10-11 |
MXPA05006197A (es) | 2005-08-19 |
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