CN1642512A - 间苯二酚衍生物在化妆品组合物中的稳定 - Google Patents
间苯二酚衍生物在化妆品组合物中的稳定 Download PDFInfo
- Publication number
- CN1642512A CN1642512A CNA038067560A CN03806756A CN1642512A CN 1642512 A CN1642512 A CN 1642512A CN A038067560 A CNA038067560 A CN A038067560A CN 03806756 A CN03806756 A CN 03806756A CN 1642512 A CN1642512 A CN 1642512A
- Authority
- CN
- China
- Prior art keywords
- resorcinol
- alkyl
- ester
- oxide
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 84
- 239000002537 cosmetic Substances 0.000 title claims abstract description 37
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 title claims description 43
- 230000006641 stabilisation Effects 0.000 title description 3
- 238000011105 stabilization Methods 0.000 title description 3
- -1 4-substituted resorcinol Chemical class 0.000 claims abstract description 49
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 31
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 57
- 229960001755 resorcinol Drugs 0.000 claims description 34
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical group O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 32
- 150000002148 esters Chemical class 0.000 claims description 20
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 19
- ALYNCZNDIQEVRV-UHFFFAOYSA-N aniline-p-carboxylic acid Natural products NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 17
- 239000004408 titanium dioxide Substances 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 12
- 239000000516 sunscreening agent Substances 0.000 claims description 12
- VGMJYYDKPUPTID-UHFFFAOYSA-N 4-ethylbenzene-1,3-diol Chemical compound CCC1=CC=C(O)C=C1O VGMJYYDKPUPTID-UHFFFAOYSA-N 0.000 claims description 8
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 claims description 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 claims description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 6
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- 239000002253 acid Substances 0.000 claims description 5
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- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 claims description 5
- 230000000475 sunscreen effect Effects 0.000 claims description 5
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 claims description 4
- 229930188104 Alkylresorcinol Natural products 0.000 claims description 4
- 241001597008 Nomeidae Species 0.000 claims description 4
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 4
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- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 claims description 4
- 235000001785 ferulic acid Nutrition 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 claims description 4
- 229960001679 octinoxate Drugs 0.000 claims description 4
- 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 claims description 4
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 claims description 4
- 239000011787 zinc oxide Substances 0.000 claims description 4
- 150000005208 1,4-dihydroxybenzenes Chemical group 0.000 claims description 3
- MEZZCSHVIGVWFI-UHFFFAOYSA-N 2,2'-Dihydroxy-4-methoxybenzophenone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1O MEZZCSHVIGVWFI-UHFFFAOYSA-N 0.000 claims description 3
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 claims description 3
- WSSJONWNBBTCMG-UHFFFAOYSA-N 2-hydroxybenzoic acid (3,3,5-trimethylcyclohexyl) ester Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C1=CC=CC=C1O WSSJONWNBBTCMG-UHFFFAOYSA-N 0.000 claims description 3
- 229920001273 Polyhydroxy acid Polymers 0.000 claims description 3
- 150000001277 beta hydroxy acids Chemical class 0.000 claims description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
- UVCJGUGAGLDPAA-UHFFFAOYSA-N ensulizole Chemical compound N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 UVCJGUGAGLDPAA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229960004881 homosalate Drugs 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 claims description 3
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 claims description 2
- NAFDCRMGWKHMJQ-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethyl 2-hydroxybenzoate Chemical compound OCCN(CCO)CCOC(=O)C1=CC=CC=C1O NAFDCRMGWKHMJQ-UHFFFAOYSA-N 0.000 claims description 2
- HHSCZZZCAYSVRK-UHFFFAOYSA-N 2-octylbenzene-1,3-diol Chemical compound CCCCCCCCC1=C(O)C=CC=C1O HHSCZZZCAYSVRK-UHFFFAOYSA-N 0.000 claims description 2
- CSHZYWUPJWVTMQ-UHFFFAOYSA-N 4-n-Butylresorcinol Chemical compound CCCCC1=CC=C(O)C=C1O CSHZYWUPJWVTMQ-UHFFFAOYSA-N 0.000 claims description 2
- 229940111759 benzophenone-2 Drugs 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- WXNRYSGJLQFHBR-UHFFFAOYSA-N bis(2,4-dihydroxyphenyl)methanone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1O WXNRYSGJLQFHBR-UHFFFAOYSA-N 0.000 claims description 2
- SODJJEXAWOSSON-UHFFFAOYSA-N bis(2-hydroxy-4-methoxyphenyl)methanone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=C(OC)C=C1O SODJJEXAWOSSON-UHFFFAOYSA-N 0.000 claims description 2
- 229940025250 camphora Drugs 0.000 claims description 2
- 239000010238 camphora Substances 0.000 claims description 2
- IAJNXBNRYMEYAZ-UHFFFAOYSA-N ethyl 2-cyano-3,3-diphenylprop-2-enoate Chemical group C=1C=CC=CC=1C(=C(C#N)C(=O)OCC)C1=CC=CC=C1 IAJNXBNRYMEYAZ-UHFFFAOYSA-N 0.000 claims description 2
- 229940068171 ethyl hexyl salicylate Drugs 0.000 claims description 2
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 claims description 2
- BEJNERDRQOWKJM-UHFFFAOYSA-N kojic acid Chemical compound OCC1=CC(=O)C(O)=CO1 BEJNERDRQOWKJM-UHFFFAOYSA-N 0.000 claims description 2
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- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 claims description 2
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- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 claims description 2
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
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- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
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Abstract
本发明涉及一种具有改进的储存稳定性的化妆品组合物,它含有微化金属氧化物和通式(I)的4-取代间苯二酚衍生物,其中每个R1和R2独立地表示氢原子、-CO-R(酰基)、-COO-R、CONHR;其中R表示饱和或不饱和的、直链或支链或环状的C1-C18烃基;R3代表(1)具有1-18个碳原子、优选2-12个碳原子的烷基,直链烷基上的一个或多个氢原子可以未取代或被甲基或乙基取代;例如R3构成直链或支链烷基,或(2)通式(II)的基团:其中X优选为氢;n是0-3,和虚线表示在该位置上的任选双键。
Description
本发明涉及含有4-取代间苯二酚衍生物的化妆品组合物,所述4-取代间苯二酚衍生物通过向组合物中引入微化金属氧化物而被稳定以抗降解。
特定的间苯二酚衍生物,特别是4-取代间苯二酚衍生物,用于护发和护肤的化妆品组合物中。间苯二酚衍生物描述在许多出版物中,包括Hu等的美国专利6132740;欧洲专利申请EP 1 134 207;和日本公开专利申请JP 2001-010925和JP 2000-327557。
间苯二酚衍生物是公知的化合物,可以通过例如如下的方法获得:使饱和羧酸和间苯二酚在氯化锌存在下缩合,所得的缩合物用锌汞齐/盐酸还原(Lille,J.Bitter,LA.Peiner.V,Tr.Nauch-Issled.Inst.Slantsev 1969,No.18,127);或通过如下的方法获得:使间苯二酚和相应的烷基醇在氧化铝催化剂存在下在200-400℃的高温下反应(英国专利1581428)。
当被引入个人护理组合物或当沉积在皮肤上时,间苯二酚衍生物容易变色,并可能由于许多因素而改变特性。在不受任何理论限制下,变色的原因的一种假设是氧化。用于皮肤增白组合物中的间苯二酚衍生物、特别是4-取代间苯二酚衍生物的变色对于想要增白皮肤的消费者而言是特别令人不快的。已经做过许多尝试来使这些缺点最小化,但是至今很少成功。
所以,需要一种能使间苯二酚衍生物、特别是4-取代间苯二酚衍生物对降解稳定的试剂。特别是,需要一种能防止皮肤增白组合物中的4-取代间苯二酚衍生物的不利变色的试剂。
申请人已经发现在个人护理组合物中组合4-取代间苯二酚衍生物与金属氧化物、特别是微化金属氧化物能够使间苯二酚衍生物颜色稳定。
因此,本发明的第一方面提供一种化妆品组合物,它含有:
a.约0.000001-50%的微化金属氧化物;
b.约0.000001-50%的下式(I)的4-取代间苯二酚衍生物:
其中每个R1和R2独立地表示氢原子、-CO-R(酰基)、-COO-R、CONHR;其中R表示饱和或不饱和的、直链或支链或环状的C1-C18烃基;R3代表:
(1)具有1-18个碳原子、优选2-12个碳原子的烷基,直链烷基上的一个或多个氢原子可以未取代或被甲基或乙基取代;例如R3构成直链或支链烷基,或
(2)下式(II)的基团:
其中X表示氢;OR1,其中R1代表氢、(C1-C6)烷基或芳基-(C1-C6)烷基;OCOR2,其中R2代表(C1-C6)烷基、芳基-(C1-C6)烷基或苯基;卤素;(C1-C6)烷基;芳基-(C1-C6)烷基,或芳基(C1-C6)烷基;或NHR1,其中R1如上所定义;
n是0-3,使得通式II的结构是5、6、7或8元环;和
虚线表示在该位置上的任选双键;和
c.一种化妆上可接受的介质。
在一个优选实施方案中,R1和/或R2中的每一个或两者都代表氢。在一个更优选的实施方案中,R1和R2都代表氢。4-取代间苯二酚衍生物包括4-直链烷基间苯二酚、4-支链烷基间苯二酚、4-环烷基间苯二酚以及它们的混合物。优选的4-取代间苯二酚衍生物包括4-乙基间苯二酚、4-异丙基间苯二酚、4-己基间苯二酚、4-环戊基间苯二酚和4-环己基间苯二酚,以及它们的酰化形式。
本发明的组合物是在感官上令人愉快的并具有改进的储存/颜色稳定性。
在这里使用的术语“化妆品组合物”表示用于局部施用到人皮肤上的组合物,包括免洗和需要洗除的产品。
在这里使用的术语“皮肤”包括面部、颈部、胸部、背部、臂部、腋部、手部、腿部和头皮上的皮肤。
除了在实施例中或另有说明,所有在此处表示材料的量或反应条件、材料的物理特性和/或应用的数字应该理解为包含“约”的情况。所有用量是以组合物的重量计,除非另有说明。
为了避免产生怀疑,术语“包含”表示包括但并非必须由其组成。换句话说,所列的步骤或选择不是穷举式的。
本发明涉及一种化妆品组合物,其中使用微化金属氧化物抑制其中存在的4-取代间苯二酚衍生物的变色。根据化妆品组合物的性质,除了具有对4-取代间苯二酚衍生物的稳定作用之外,金属氧化物还可以提供防晒效果。
本发明的组合物通常含有约0.000001-50%的金属氧化物和约0.000001-50%的4-取代间苯二酚。本发明组合物的特别益处在于4-取代间苯二酚可以用微化金属氧化物颗粒进行抗变色稳定。
合适的用作4-取代间苯二酚衍生物颜色稳定剂的微化金属氧化物包括具有小于约100nm的非常小粒度的那些,优选小于约50nm,更优选约10-40nm,最优选约15-35nm。优选的金属氧化物是微化二氧化钛和氧化锌,以及它们的混合物,这是因为它们的有效性和商业可得性。
优选的微化二氧化钛和氧化锌颗粒的例子分别列在下面的表1和2中。
表1微化二氧化钛
颗粒
级别 TIO2(%) 主要改性剂 粒度(nm) 生产公司
oeMT-100S min.80 月桂酸铝 15 Tayca Co.
氢氧化铝
oeMT-100T min.78 硬脂酸铝 15 Tayca Co.
氢氧化铝
oeMT-100TV min.78 硬脂酸铝 15 Tayca Co.
氢氧化铝
oeMT-100Z min.73 硬脂酸铝 15 Tayca Co.
氢氧化铝
oeMT-100F min.78 硬脂酸铁 15 Tayca Co.
氢氧化铁
oeMT-150W min.91 - 15 Tayca Co.
oeMT-100AQ min.70 氧化铝、硅石、 15 Tayca Co.
藻酸
oeMT-100SA min.84 氧化铝、硅石 15 Tayca Co.
oeMT-100HD min.80 氧化铝、氧化锆 15 Tayca Co.
oeMT-100AS min.78 氧化铝、硅石、 15 Tayca Co.
硅氧烷
oeSMT-100SAS min.78 氧化铝、硅石、 15 Tayca Co.
硅氧烷
oeMT-500B min.96 - 35 Tayca Co.
oeMT-500H min.90 氧化铝 35 Tayca Co.
oeMT-500SA min.85 氧化铝、硅石 35 Tayca Co.
oeMT-500HD min.85 氧化铝、氧化锆 30 Tayca Co.
oeMT-500SAS min.85 氧化铝、硅石、 35 Tayca Co.
硅氧烷
oeSMT-500SAS min.80 氧化铝、硅石、 35 Tayca Co.
硅氧烷
oeMT-600B min.96 - 50 Tayca Co.
oeMT-600SA min.84 氧化铝、硅石 50 Tayca Co.
oeMT-700HD min.85 氧化铝、氧化锆 50 Tayca Co.
DEA-3824999 <100 The Boots Co.PLC
表2微化氧化锌
300系列
级别 外观 粒度(nm) 主要改性剂 供应商
oeMZ-300 无 Tayca Co.
二甲基硅氧烷
oeMZ-303S 白色粉末 30-40 (methicone)3% Tayca Co.
oeMZ-303M 聚二甲基硅氧烷3% Tayca Co.
500系列
级别 外观 粒度(nm) 主要改性剂 供应商
oeMZ-500 无 Tayca Co.
oeMZ-505S 白色粉末 20-30 二甲基硅氧烷5% Tayca Co.
oeMZ-505M 聚二甲基硅氧烷5% Tayca Co.
700系列
级别 外观 粒度(nm) 主要改性剂 供应商
oeMZ-700 无 Tayca Co.
oeMZ-707S 白色粉末 10-20 二甲基硅氧烷7% Tayca Co.
oeMZ-707M 聚二甲基硅氧烷7% Tayca Co.
微化金属氧化物在化妆品组合物中的用量优选是约0.01-25%,更优选约0.1-5%。
微化金属氧化物可以是水分散性的或油分散性的。例如,根据本发明,水分散性二氧化钛是一种微化二氧化钛,其颗粒是未涂覆的或被一种材料涂覆以赋予颗粒亲水性。这种材料的例子包括氧化铝和硅酸铝。根据本发明,油分散性二氧化钛是一种微化二氧化钛,其颗粒显示疏水表面性能,例如为此可以用金属皂涂覆,例如硬脂酸铝、月桂酸铝或硬脂酸锌,或用有机硅化合物涂覆。
当被引入本发明的化妆品组合物中时,微化金属氧化物还可以用于提供抵抗过度日晒不利作用的有利保护,详见下面关于任选的防晒材料的叙述。许多金属氧化物是UV分散剂或UV封锁剂,特别是二氧化钛细粉。
能有效抑制4-取代间苯二酚衍生物变色的金属氧化物的量通过实验确定。金属氧化物和4-取代间苯二酚衍生物在组合物中以1∶10000至10000∶1的金属氧化物:4-取代间苯二酚重量比存在,优选1∶1000至1∶5000,更优选1∶1至1∶1000。
合适的式(I)的间苯二酚衍生物特别需要抗变色的稳定作用,因为它们用作皮肤增白剂,其中使用:
其中每个R1和R2独立地表示氢原子、-CO-R(酰基)、-COO-R、CONHR;后三个基团分别由下式A表示:
其中R表示饱和或不饱和的、直链或支链或环状的C1-C18烃基。在一个优选的实施方案中,R1和/或R2中的每一个或这两者代表氢。在一个更优选的实施方案中,R1和R2都代表氢。
R3代表:
(1)具有1-18个碳原子、优选2-12个碳原子的烷基,直链烷基上的一个或多个氢原子可以未取代或被甲基或乙基取代;例如R3构成直链或支链烷基,或
(2)下式(II)的基团,其中X和n应该如下定义
在上式(1)中,R3代表的未取代的直链烷基团优选具有2-12个碳原子,可以包括乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基和十二烷基。这些直链基团的一个或多个氢原子可以被甲基或乙基取代。取代烷基的具体例子包括异丙基、异丁基、异戊基、2-甲基己基等。优选的烷基是其中R3代表乙基、丙基、丁基、戊基、己基、庚基或辛基的那些。最优选的烷基间苯二酚是其中R代表乙基、丁基或己基的那些。
在其中R3代表上式(II)结构的间苯二酚衍生物的情况下,通式(I)的间苯二酚衍生物称为4-环烷基间苯二酚,并由下式(III)表示:
X表示氢;OR1,其中R1代表氢、(C1-C6)烷基或芳基-(C1-C6)烷基;OCOR2,其中R2代表(C1-C6)烷基、芳基-(C1-C6)烷基或苯基;卤素;(C1-C6)烷基;芳基-(C1-C6)烷基,或芳基(C1-C6)烷基;或NHR1,其中R1如上所定义;
n是0-3;和
虚线表示在该位置上的任选双键。
4-环烷基间苯二酚的更具体的例子包括:
(a)式(III)的化合物,其中单键连接虚线处的两个碳原子;
(b)式(III)的化合物,其中n是1;
(c)式(III)的化合物,其中X是氢;
(d)式(III)的化合物,其中X是氢、甲基或乙基;
(e)式(III)的化合物,其中n是0;
(f)式(III)的化合物,其中n是2;和
(g)式(III)的化合物,其中X是苄氧基。
优选的式(III)化合物是4-环戊基间苯二酚、4-环己基间苯二酚、4-环庚基间苯二酚4-环辛基间苯二酚。最优选的式(III)化合物是4-环己基间苯二酚和4-环戊基间苯二酚。
间苯二酚衍生物的量优选是化妆品组合物总量的约0.00001-10%,更优选约0.001-7%,最优选约0.01-5%。
优选的化妆品组合物是适合于施用于人皮肤的那些,除了4-取代间苯二酚衍生物之外,其任选地、但是优选地包含任选的护肤剂。
合适的额外护肤剂包括抗老化剂、抗皱剂、皮肤增白剂、抗痤疮剂和皮脂减少剂。这些的例子包括α-羟基酸和酯,β-羟基酸和酯,多羟基酸和酯,曲酸和酯,阿魏酸和阿魏酸酯衍生物,香草酸和酯,二元酸(例如癸二酸(sebacid)和壬二酸(azoleic acids))和酯,视黄醇、视黄醛、视黄基酯,氢醌,叔丁基氢醌,桑树提取物,甘草提取物,和除了这里所述4-取代间苯二酚衍生物之外的间苯二酚衍生物。
护肤剂与微化金属氧化物和本发明的间苯二酚衍生物一起通常与化妆品基料一起使用。合适的化妆上可接受的介质是本领域技术人员熟知的。化妆品基料可以是任何常用于护肤剂的基料,并不是关键的。可向其中加入本发明护肤剂的特定化妆品制剂包括乳油、软膏、乳液、洗剂、油、小包装和无纺抹布。乳油基料包括例如蜂蜡、十六醇、硬脂酸、甘油、丙二醇、单硬脂酸丙二醇酯、聚氧乙烯十六烷基醚等。洗剂基料包括例如油醇、乙醇、丙二醇、甘油、月桂醚、失水山梨醇一月桂酸酯等。
化妆上可接受的介质可以用作组合物中护肤成分的稀释剂、分散剂或载体,从而当将组合物施用到皮肤上时促进它们的分布。
介质可以是含水的、无水的或是乳液。优选的是,组合物是含水的或是乳液,特别是油包水或水包油乳液,优选水包油乳液。当存在水时,水的量可以是5-99重量%,优选20-70重量%,最好是40-70重量%。
除了水之外,挥发性较强的溶剂也可以用作本发明组合物中的载体。最优选的是一元C1-C3链烷醇。这些包括乙醇、甲醇和异丙醇。一元链烷醇可以是1-70重量%,优选10-50重量%,最好是15-40重量%。
润肤剂材料也可以用作化妆上可接受的载体。它们可以硅油和合成酯的形式。润肤剂的量可以是0.1-50重量%,优选1-20重量%。
硅油可以分成挥发性和非挥发性的。这里使用的术语“挥发性”表示在环境温度下具有可测量的蒸气压的那些材料。挥发性硅油优选选自环状或线型的聚二甲基硅氧烷,其含有3-9个、优选4-5个硅原子。线型硅氧烷材料通常具有在25℃下小于约5厘沲的粘度,而环状材料通常具有小于约10厘沲的粘度。
用作润肤剂的非挥发性硅油包括聚烷基硅氧烷,聚烷基芳基硅氧烷和聚醚硅氧烷共聚物。在这里使用的基本非挥发性聚烷基硅氧烷包括例如在25℃下粘度为约5-25000000厘沲的聚二甲基硅氧烷。在本发明组合物中优选使用的非挥发性润肤剂是在25℃下粘度为约10-400厘沲的聚二甲基硅氧烷。
合适的酯类润肤剂是:
(1)具有10-20个碳原子的脂肪酸的链烯基或烷基酯。例子包括新戊酸异花生基酯、异壬酸异壬基酯、肉豆蔻酸油基酯、硬脂酸油基酯和油酸油基酯;
(2)醚酯,例如乙氧基化脂肪醇的脂肪酸酯;
(3)多元醇酯,包括乙二醇单-和二-脂肪酸酯,二甘醇单-和二-脂肪酸酯,聚乙二醇(200-6000)单-和二-脂肪酸酯,丙二醇单-和二-脂肪酸酯,聚丙二醇2000单油酸酯,聚丙二醇2000单硬脂酸酯,乙氧基化丙二醇单硬脂酸酯,甘油单-和二-脂肪酸酯,聚甘油多脂肪酸酯,乙氧基化甘油单硬脂酸酯,1,3-丁二醇单硬脂酸酯,1,3-丁二醇二硬脂酸酯,聚氧乙烯多元醇脂肪酸酯,失水山梨醇脂肪酸酯,和聚氧乙烯失水山梨醇脂肪酸酯是令人满意的多元醇酯;
(4)蜡酯,例如蜂蜡、鲸蜡、肉豆蔻酸肉豆蔻酯,硬脂酸硬脂基酯和山俞酸花生基酯;和
(5)固醇酯,例子是胆固醇脂肪酸酯。
具有10-30个碳原子的脂肪酸也可以作为化妆上可接受的载体用于本发明的组合物。其例子是壬酸、月桂酸、肉豆蔻酸、棕榈酸、硬脂酸、异硬脂酸、羟基硬脂酸、油酸、亚油酸、蓖麻油酸、花生酸、山俞酸和芥酸。
多元醇型的润湿剂也可以作为化妆上可接受的载体用于本发明的组合物。润湿剂帮助增加润肤剂的效果、降低皮肤干燥和改进肤感。典型的多元醇包括甘油、聚亚烷基二醇和更优选亚烷基多元醇及其衍生物,包括丙二醇、二丙二醇、聚丙二醇、聚乙二醇和其衍生物、山梨醇、羟基丙基山梨醇、己二醇、1,3-丁二醇、1,2,6-己三醇、乙氧基化甘油、丙氧基化甘油以及它们的混合物。润湿剂的用量可以是组合物重量的0.5-30%,优选1-15%。
增稠剂也可以作为本发明组合物的化妆上可接受的载体的一部分。增稠剂包括交联丙烯酸酯(例如Carbopol 982)、疏水改性的丙烯酸酯(例如Carbopol 1382)、纤维素衍生物和天然树胶。有用的纤维素衍生物是羧甲基纤维素钠、羟丙基甲基纤维素、羟丙基纤维素、羟乙基纤维素、乙基纤维素和羟甲基纤维素。适用于本发明的天然树胶包括瓜尔胶、黄原胶、菌核、卡拉胶、果胶以及这些树胶的组合物。增稠剂的用量可以是0.0001-5重量%,通常是0.001-1重量%,优选0.01-0.5重量%。
水、溶剂、硅氧烷、酯、脂肪酸、润湿剂和/或增稠剂一起将构成化妆上可接受的载体,其量通常是1-99.9重量%,优选80-99重量%。
油或油状物质可以与乳化剂一起存在,以便提供油包水乳液或水包油乳液,这主要取决于所用乳化剂的平均亲水亲油平衡值(HLB)。
表面活性剂也可以存在于本发明的化妆品组合物中。对于免洗产品,表面活性剂的总浓度将是组合物重量的0.1-40%,优选1-20%,最好是1-5%。对于要洗除的产品,例如清洁剂和皂类,表面活性剂的总浓度将是约1-90%。表面活性剂可以选自阴离子、非离子、阳离子和两性的活性物质。特别优选的非离子表面活性剂是具有以下的那些:以每摩尔疏水物质计与2-100摩尔氧化乙烯或氧化丙烯缩合的C10-C20脂肪醇或酸疏水物质;与2-20摩尔氧化烯缩合的C2-C10烷基酚;乙二醇的单-和二-脂肪酸酯;脂肪酸单甘油酯;失水山梨醇、单-和二-C8-C20脂肪酸;氧化乙烯/氧化丙烯的嵌段共聚物;和聚氧乙烯失水山梨醇以及它们的混合物。烷基多苷和多糖脂肪酰胺(例如甲基葡糖酰胺)也是合适的非离子表面活性剂。
优选的阴离子表面活性剂包括皂、烷基醚硫酸盐和磺酸盐,烷基硫酸盐和磺酸盐,烷基苯磺酸盐,烷基和二烷基磺基琥珀酸盐,C8-C20酰基羟乙基磺酸盐,酰基谷氨酸盐,C8-C20烷基醚磷酸盐,以及它们的混合物。
本发明的化妆品组合物任选地含有泡沫化表面活性剂。“泡沫化表面活性剂”表示这样的表面活性剂,当其与水混合并机械搅拌时,产生了泡沫或起泡。优选的是,泡沫化表面活性剂应当是温和的,这表示它必须提供足够的清洗或洗涤剂作用,但是不会过度使皮肤干燥,并且满足上述泡沫化标准。本发明的化妆品组合物可以含有浓度为约0.01-50%的泡沫化表面活性剂。
在本发明的化妆品组合物中,可以加入任选的组分例如各种其它增塑剂、弹性体、菱锌矿、颜料、抗氧化剂、螯合剂和香料;以及额外的防晒剂,例如有机防晒剂,特别是Parsol 1789和Parsol MCX(商品名)。
其它次要的助剂组分也可以引入本发明的化妆品组合物中。这些成分可以包括着色剂、不透明剂和香料。这些其它次要的助剂组分的用量可以是组合物重量的0.001-20%。
当用作防晒剂时,金属氧化物可以单独使用或作为混合物使用和/或与有机防晒剂组合使用。有机防晒剂的例子包括但不限于下表列出的那些:
表3有机防晒剂
CTFA名称 商品名 供应商
二苯酮-3 UVINUL M-40 BASF Chemical Co.
二苯酮-4 UVINUL MS-40 BASF Chemical Co.
二苯酮-8 SPECRA-SORB UV-24 American Cyanamide
DEA(二乙醇胺)
甲氧基肉桂酸酯 BERNEL HYDRO Bernel Chemical
对氨基苯甲酸乙基二羟基丙酯 AMERSCREEN P Amerchol Corp.
对氨基苯甲酸甘油酯 NIPA G.M.P.A. Nipa Labs.
Homosalate KEMESTER HMS Hunko Chemical
邻氨基苯甲酸甲酯 SUNAROME UVA Felton Worldwide
氰双苯丙烯酸辛酯 UVINUL N-539 BASF Chemical Co.
对氨基苯甲酸辛基二甲酯 AMERSCOL Amerchol Corp.
甲氧基肉桂酸辛酯 PARSOL MCX Bernel Chemical
水杨酸辛酯 SUNAROME WMO Felton Worldwide
PABA(对氨基苯甲酸) PABA National Starch
2-苯基苯并咪唑-5-磺酸 EUSOLEX 232 EM Industries
水杨酸三乙醇胺酯 SUNAROME W Felton Worldwide
3-(4-甲基亚苄基)-樟脑 EUSOLEX 6300 EM Industries
二苯酮-1 UVINUL 400 BASF Chemical Co.
二苯酮-2 UVINUL D-50 BASF Chemical Co.
二苯酮-6 UVINUL D-49 BASF Chemical Co.
二苯酮-12 UVINUL 408 BASF Chemical Co.
4-异丙基二苯甲酰基甲烷 EUSOLEX 8020 EM Industries
丁基甲氧基二苯甲酰基甲烷 PARSOL 1789 Givaudan Corp.
Etocrylene UVINUL N-35 BASF Chemical Co.
在化妆品组合物中,有机防晒剂的用量是约0.01-20重量%,优选约0.1-10重量%。
优选的有机防晒剂是Parsol MCX和Parsol 1789,这是由于它们的有效性和商业可得性。
本发明的组合物主要作为用于局部施用到人皮肤上的个人护理产品,以及用于保护暴露的皮肤免受过度日晒的伤害。
在使用中,从适宜的容器或施用器将少量组合物例如约0.1-5ml施用在皮肤的暴露区域上,和必要时用手或手指或合适的工具将其铺展和/或按压入皮肤中。
本发明的化妆品组合物可以配制成粘度为4000-10000mPas的洗剂,粘度为10000-20000mPas的流体乳油,或粘度为20000-100000mPas或以上的乳油,均在25℃下检测。该组合物可以包装在合适的容器中以适合其粘度和消费者的预期用途。例如,洗剂或流体乳油可以包装在瓶中或辊球施用器或泵式驱动的气溶胶设备或装有适合手指操作的泵的容器中。当组合物是乳油时,可以简单地储存在不变形的瓶或压缩容器中,例如管或带盖子的罐。
因此,本发明还提供一种含有上述定义的化妆可接受的组合物的密闭容器。
以下具体实施例进一步说明本发明,但是本发明不限于此。在所有实施例中,金属氧化物是Tayca Co.获得的,特别使用MT-100Z材料。
实施例
实施例1-8
制备本发明范围内的化妆品组合物。
表4
组分商标和CTFA名称 | 相 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 |
硬脂酸 | A | 14.9 | 14.9 | 12.9 | 17.9 | 18.0 | 18.0 | 18.0 | 18.0 |
棕榈醇硫酸钠(Sodium ceteary sulfate) | A | 1.0 | 1.0 | 1.5 | 1.5 | 1 | 1 | 1 | 1 |
Myrj 59 | A | 2.0 | 1.5 | 2 | 2 | 2 | 2 | 2 | 2 |
Span 60 | A | 2.0 | 1.5 | 2 | 2 | 2 | 2 | 2 | 2 |
对羟基苯甲酸丙酯 | A | 0.10 | 0.10 | 0.10 | 0.10 | 0.10 | 0.10 | 0.10 | 0.10 |
BHT | A | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 |
二甲基硅氧烷 | A | 0.50 | 0.75 | 0.75 | 0.75 | 0.75 | 0.75 | ||
水 | B | BAL* | BAL | BAL | BAL | BAL | BAL | BAL | BAL |
EDTA | B | 0.04 | 0.04 | 0.04 | 0.04 | 0.04 | 0.04 | 0.04 | 0.04 |
Pemulen TR 2 | B | 0.10 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | ||
对羟基苯甲酸甲酯 | B | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 |
Parsol MCX(有机防晒剂) | C | 0.75 | 1.25 | 1 | 1 | 0.75 | 0.75 | 0.75 | 0.75 |
Parsol 1789(有机防晒剂) | C | 0.40 | 0.4 | 0.4 | 0.4 | 0.4 | 0.4 | 0.4 | |
微化二氧化钛 | C | 0.2 | 0.2 | 0.2 | 0.2 | ||||
丙二醇 | D | 8 | 8 | 8 | 8 | ||||
Transcutol | D | 4 | 4 | 4 | 4 | ||||
4-丁基间苯二酚 | D | 0.05 | 2.0 | 2.0 | 1 | ||||
4-乙基间苯二酚 | D | 0.30 | |||||||
4-己基间苯二酚 | D | 0.42 | |||||||
间苯二酚 | D | 0.24 | |||||||
2-甲基间苯二酚 | D | 0.27 |
*BAL=平衡到100%
在上表中,实施例1-8的组合物如下制备。将相A在75℃加热。将相B在与相A的容器分离的容器中加热至75℃。然后,停止加热,将各相混合。预先混合相C并加热,然后立即在相A和相B混合之后加入。相D预先溶解,并于60℃加入主要反应器中。将混合物冷却到40℃,然后包装。
实施例9
该实施例证明了微化金属氧化物对4-取代间苯二酚衍生物的储存稳定作用。在该实验中,通过间苯二酚衍生物颜色随时间变化表示的储存稳定性在金属氧化物存在和不存在下进行检测。
TiO2对含有4-取代间苯二酚衍生物的配料的颜色稳定作用通过检测不同配料随时间的色度L*值评价(Luminance,或亮度)。L*随时间的降低表示由于间苯二酚衍生物的分解导致的从白色初始配料的颜色变暗。
在下表5中,在含有和不含二氧化钛情况下,各配料之间的ΔL值表示在对比例之间的色差程度。正的ΔL值表示二氧化钛-间苯二酚配料比不含二氧化钛的对照间苯二酚配料在此时更白。因此,可见二氧化钛具有明显的颜色稳定效果,特别是对含有4-取代间苯二酚的配料而言。
上表中的实施例5-8的化妆品组合物进行储存,并检测变色稳定性。在这些实施例中的间苯二酚和4-取代间苯二酚具有相等的摩尔含量,即2.17毫摩尔。实施例8的对比组合物通过从实施例5-8的组合物中除去间苯二酚或其衍生物来获得。产品配料在120ml玻璃罐中在烘箱中于45℃储存56天。
检测化妆品配料的CIE L*a*b*颜色的工序
用刮勺将组合物均匀地涂在UV透明石英片上形成膜(10.16cm×10.48cm×0.32cm,4″×4 1/8″×1/8″)。使用8路湿膜涂布器(PaulGardner Company,Inc.),通路宽度是7.62cm(3″)。手工将涂布器从片上拉过,厚度是4mm。
将片反转,使薄膜面向实验台上部,并悬挂在黑色实验台上部以上3.81cm
(实验台上部的L*a*b*读数是L*=27.5,a*=0.5,b*=-0.6)。然后,在白色校正色砖上校准手持的Minolta CR10色度计(L 98.2,a 0.2,b 1.2)。色度计然后放在片上部,读取三个CIE L*a*b*读数。
-L*=黑色至白色(亮度)0-100[L*=0时代表黑色]
-a*=绿色至红色,-60至+60
-b*=蓝色至黄色,-60至+60
在本分析中使用配料薄膜的L*值。对于每个数据,得到在0、14、28和56天时三个读数的平均值。
结果列在下表中。
表5
用于间苯二酚配料的含二氧化钛的基料调节ΔL值-不含二氧化钛的基料调节ΔL值* | |||
储存时间,天 | 间苯二酚 | 4-乙基间苯二酚 | 4-己基间苯二酚 |
0 | 0 | 0 | 0 |
14 | 0.9 | 12.0 | 7.7 |
28 | -2 | 4.6 | 0.1 |
56 | 1.1 | 7.6 | 3.7 |
*计算值
对于每个时间点:
其中tx=按天计的储存时间;即,t0=0天,L*是检测的L*值。
上表5的结果显示向本发明组合物中添加二氧化钛稳定了间苯二酚衍生物随时间的降解,特别是对于4-取代间苯二酚衍生物。
应当理解的是,这里描述的本发明的具体形式仅仅用于说明。可以在不明显偏离公开内容下的改变,包括但不限于在本说明书中暗示的那些。因此,应当参考所附的权利要求确定本发明的整个范围。
Claims (13)
1.一种局部化妆品组合物,它含有:
a.约0.000001-50%的微化金属氧化物;
b.约0.000001-50%的通式(I)的4-取代间苯二酚衍生物:
其中每个R1和R2独立地表示氢原子、-CO-R、-COO-R、CONHR;
其中R表示饱和或不饱和的、直链或支链或环状的C1-C18烃基;R3代表具有1-18个碳原子的烷基,或通式(II)的基团:
其中X表示氢;OR1,其中R1代表氢、(C1-C6)烷基或芳基-(C1-C6)烷基;OCOR2,其中R2代表(C1-C6)烷基、芳基-(C1-C6)烷基或苯基;卤素;(C1-C6)烷基;芳基-(C1-C6)烷基,或芳基-(C1-C6)烷基;或NHR1,其中R1如上所定义;
n是0-3,使得通式II的结构是5、6、7或8元环;和
虚线表示在该位置上的任选双键;和
c.一种化妆上可接受的介质。
2.权利要求1的组合物,其中微化金属氧化物具有小于约100nm的粒度。
3.权利要求1或2的组合物,其中微化金属氧化物选自二氧化钛、氧化锌以及它们的混合物。
4.前述权利要求任一项的组合物,其中微化金属氧化物以至少能抑制4-取代间苯二酚衍生物变色的有效量存在。
5.权利要求4的组合物,其中微化金属氧化物的量是约0.1-5%。
6.前述权利要求任一项的组合物,其中4-取代间苯二酚选自4-直链烷基间苯二酚、4-支链烷基间苯二酚、4-环烷基间苯二酚以及它们的混合物和它们的酰化形式。
7.权利要求6的组合物,其中4-取代间苯二酚选自4-环戊基间苯二酚、4-环己基间苯二酚、以及它们的混合物。
8.权利要求6的化妆品组合物,其中4-取代间苯二酚选自4-甲基间苯二酚、4-乙基间苯二酚、4-丙基间苯二酚、4-异丙基间苯二酚、4-丁基间苯二酚、4-戊基间苯二酚、4-己基间苯二酚、4-庚基间苯二酚、4-辛基间苯二酚、4-壬基间苯二酚、4-癸基间苯二酚、4-十一烷基间苯二酚、4-十二烷基间苯二酚、4-环戊基间苯二酚、4-环己基间苯二酚、4-环庚基间苯二酚、4-环辛基间苯二酚、以及它们的混合物。
9.前述权利要求任一项的化妆品组合物,其还包含护肤剂,选自α-羟基酸和酯,β-羟基酸和酯,多羟基酸和酯,曲酸和酯,阿魏酸和阿魏酸酯衍生物,香草酸和酯,二元酸和酯,视黄醇、视黄醛、视黄基酯,氢醌,叔丁基氢醌,间苯二酚衍生物,以及它们的混合物。
10.权利要求9的化妆品组合物,其中护肤剂选自α-羟基酸,β-羟基酸,多羟基酸,氢醌,叔丁基氢醌,间苯二酚衍生物,以及它们的混合物。
11.前述权利要求任一项的组合物,其还包含有机防晒剂。
12.权利要求11的组合物,其中防晒剂选自二苯酮-3、二苯酮-4、二苯酮-8、二乙醇胺、甲氧基肉桂酸酯、对氨基苯甲酸乙基二羟基丙酯、对氨基苯甲酸甘油酯、Homosalate、邻氨基苯甲酸甲酯、氰双苯丙烯酸辛酯、对氨基苯甲酸辛基二甲酯、甲氧基肉桂酸辛酯(Parsol MCX)、水杨酸辛酯、对氨基苯甲酸、2-苯基苯并咪唑-5-磺酸、水杨酸三乙醇胺酯、3-(4-甲基亚苄基)-樟脑、二苯酮-1、二苯酮-2、二苯酮-6、二苯酮-12、4-异丙基二苯甲酰基甲烷、丁基甲氧基二苯甲酰基甲烷(Parsol1789)、氰双苯丙烯酸乙酯(Etocrylene),以及它们的混合物。
13.一种化妆品组合物,它包含:
a.被微化金属氧化物稳定的4-取代间苯二酚衍生物;
b.护肤剂,和
c.化妆上可接受的介质;
其中微化金属氧化物的存在量是该化妆品组合物的约0.0001-5重量%;和
微化金属氧化物与4-取代间苯二酚衍生物的重量比是约10000∶1至约1∶10000。
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US36692402P | 2002-03-22 | 2002-03-22 | |
US60/366,924 | 2002-03-22 |
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US (1) | US6863897B2 (zh) |
JP (1) | JP2005527534A (zh) |
KR (1) | KR20040091757A (zh) |
CN (1) | CN1293857C (zh) |
AU (1) | AU2003218759A1 (zh) |
BR (1) | BRPI0307687B1 (zh) |
MX (1) | MXPA04008842A (zh) |
WO (1) | WO2003080002A1 (zh) |
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- 2003-03-13 KR KR10-2004-7014632A patent/KR20040091757A/ko not_active Application Discontinuation
- 2003-03-13 BR BRPI0307687-3A patent/BRPI0307687B1/pt active IP Right Grant
- 2003-03-13 MX MXPA04008842A patent/MXPA04008842A/es active IP Right Grant
- 2003-03-13 AU AU2003218759A patent/AU2003218759A1/en not_active Abandoned
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CN102811771A (zh) * | 2009-10-09 | 2012-12-05 | 拜尔斯道夫股份有限公司 | 具有4-正丁基间苯二酚与一种或多种亚硫酸盐、特别是亚硫酸氢盐和/或二亚硫酸盐的组合的美容用或皮肤病用制剂 |
CN110099665A (zh) * | 2016-12-21 | 2019-08-06 | 荷兰联合利华有限公司 | 螯合剂用于改善间苯二酚的颜色稳定性的用途 |
US11478411B2 (en) | 2016-12-21 | 2022-10-25 | Conopco, Inc. | Use of chelating agents for improving color stability of resorcinol |
CN114599337A (zh) * | 2019-10-25 | 2022-06-07 | 联合利华知识产权控股有限公司 | 具有增强的颜色稳定性的化妆品组合物 |
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JP2005527534A (ja) | 2005-09-15 |
MXPA04008842A (es) | 2004-11-26 |
BR0307687A (pt) | 2005-01-11 |
CN1293857C (zh) | 2007-01-10 |
US6863897B2 (en) | 2005-03-08 |
BRPI0307687B1 (pt) | 2015-06-23 |
WO2003080002A1 (en) | 2003-10-02 |
US20030180234A1 (en) | 2003-09-25 |
AU2003218759A1 (en) | 2003-10-08 |
KR20040091757A (ko) | 2004-10-28 |
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