JP5065029B2 - 活性又は官能性有機化合物用可溶化剤 - Google Patents
活性又は官能性有機化合物用可溶化剤 Download PDFInfo
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- JP5065029B2 JP5065029B2 JP2007534560A JP2007534560A JP5065029B2 JP 5065029 B2 JP5065029 B2 JP 5065029B2 JP 2007534560 A JP2007534560 A JP 2007534560A JP 2007534560 A JP2007534560 A JP 2007534560A JP 5065029 B2 JP5065029 B2 JP 5065029B2
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- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 229940113124 polysorbate 60 Drugs 0.000 description 1
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- 229940094546 ppg-2 isoceteth-20 acetate Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
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- 230000002335 preservative effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
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- 238000002310 reflectometry Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 1
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
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- KJCLYACXIWMFCC-UHFFFAOYSA-M sodium;5-benzoyl-4-hydroxy-2-methoxybenzenesulfonate Chemical compound [Na+].C1=C(S([O-])(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 KJCLYACXIWMFCC-UHFFFAOYSA-M 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
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- 229940033331 soy sterol Drugs 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
- 229960002256 spironolactone Drugs 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940100459 steareth-20 Drugs 0.000 description 1
- 239000002602 strong irritant Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 230000037072 sun protection Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- BORJONZPSTVSFP-UHFFFAOYSA-N tetradecyl 2-hydroxypropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)O BORJONZPSTVSFP-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- 239000002341 toxic gas Substances 0.000 description 1
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- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- ZQTYRTSKQFQYPQ-UHFFFAOYSA-N trisiloxane Chemical compound [SiH3]O[SiH2]O[SiH3] ZQTYRTSKQFQYPQ-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 150000003681 vanadium Chemical class 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0216—Solid or semisolid forms
- A61K8/0229—Sticks
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
- A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
- A61Q1/06—Lipsticks
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
-
- 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
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- 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
- A61Q19/08—Anti-ageing preparations
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09G—POLISHING COMPOSITIONS; SKI WAXES
- C09G1/00—Polishing compositions
- C09G1/06—Other polishing compositions
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- Life Sciences & Earth Sciences (AREA)
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- Organic Chemistry (AREA)
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- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Emergency Medicine (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
Description
本発明の典型的な可溶化剤の作製方法を、下記の実施例により説明する。従って、安息香酸2-フェニルエチル可溶化剤は、触媒、例えば、約180℃を超える温度、好ましくは約190〜220℃でシュウ酸スズ(FASCAT 2001(登録商標))等のルイス酸触媒、又は好ましくは約150〜170℃でメタンスルホン酸等のブレンステッド(‘強’)酸触媒の存在下において、2-フェニルエタノール(フェネチルアルコール)及び安息香酸を反応させることにより調製される。亜リン酸トリイソデシル(TDP)及び次亜リン酸(HPA)等の添加剤は、生成物の色彩を改良することができる。精製は、過剰な2-フェニルエタノールの蒸留又は炭酸ナトリウム水溶液での過剰な安息香酸の抽出と、活性炭での処理を含む。代わりに、生成物のほとんどを高真空下での蒸留により精製することができる。
活性UVA及びUVB化合物、例えば、アボベンゼン、ベンゾフェノン-3及び4-メチルベンジリデンカンファーを含有する日焼け止め剤組成物等の製剤は、安息香酸2-フェニルエチル又は本発明の他の化合物中で効果的に可溶化された。UVB部分に比べてそれらの吸収スペクトルのUVA成分の増大、SPFの上昇、及び増大した臨界波長が、一般に観測された。
安息香酸2-フェニルエチルの製造(ルイス酸触媒)
温度計、機械攪拌機、窒素注入管、及びリービッヒ冷却器/受けフラスコを取り付けた、2Lで四つ首の丸底フラスコに、安息香酸671.7g(5.50mol,1.00当量)、2-フェニルエタノール739.1g(6.05mol,1.10当量)及びFascat2001(登録商標)2.5g(0.2%w/w)を装填した。その系を、全ての安息香酸が溶解するまで、緩徐な攪拌(<50rpm)と共に穏やかに加熱した。機械的真空ポンプ(50〜100torr)を用いる真空排気/窒素充填の3回のサイクルで空気を除去した。攪拌速度を約200rpmまで上昇させ、窒素の散布を0.2scfhに設定し、反応混合物を180℃まで加熱した。1時間保持した後、留出物38.3gを集めた。アルコール(9.1g)を分離し、反応混合物に戻した。温度を190℃まで上昇させ、1時間保持し、更に留出物45.2gを集めた。アルコール(16.0g)を分離し、戻した。温度を200℃まで上昇させ、1時間保持し、更に留出物33.5gを集めた。アルコール(8.2g)を分離し、戻した。最後に、温度を210℃まで上昇させ、窒素の散布を0.5scfhまで上昇させた。1時間保持した後、留出物21.2gを集め、アルコール8.0gを分離したが、戻さなかった。反応混合物を室温まで冷却し、分析用に採取した。酸価は4.04mgKOH/g(転化率98.3%)であり、APHA色相は29であった。過剰の2-フェニルエタノール(GLCにより4.4%)を175〜180℃(20torr, 窒素掃引0.5scfh)で2時間の減圧蒸留により除去した。APHA色相は40であった。活性炭(37.1g,3%w/w)を加えて、その混合物を真空(50〜70torr)下で1時間75〜80℃にて加熱した。混合物を室温まで冷却し、セライト(登録商標)によってろ過し、安息香酸2-フェニルエチル1074g(86%)を得た(GLCによる純度99.6%):残留アルコール<0.05%(GLC);APHA色相12;酸価0.98mgKOH/g;けん化価244mgKOH/g。
安息香酸2-フェニルエチルの製造(ブレンステッド酸触媒)
温度計、機械攪拌機、窒素注入管、及びリービッヒ冷却器/受けフラスコを取り付けた、2Lで四つ首の丸底フラスコに、安息香酸671.7g(5.50mol,1.00当量)、2-フェニルエタノール806.3g(6.60mol,1.20当量)、メタンスルホン酸(MSA)2.5g(0.2%w/w,0.47mol%)及び亜リン酸トリイソデシル(TDP)1.25g(0.1%w/w)を装填した。その系を、全ての安息香酸が溶解するまで、緩徐な攪拌(<50rpm)と共に穏やかに加熱した。機械的真空ポンプ(50〜100torr)を用いる真空排気/窒素充填の3回のサイクルで空気を除去した。攪拌速度を約200rpmまで上昇させ、窒素の散布を0.2scfhに設定し、反応混合物を150℃まで加熱した。1時間保持した後、温度を160℃まで上昇させ、窒素の散布を0.5scfhまで上昇させた。1時間保持した後、温度を170℃まで上昇させ、2時間保持した。反応混合物を室温まで冷却し、分析用に採取した。酸価は5.4mgKOH/g(MSAについて補正した安息香酸の転化率98.1%)であり、APHA色相は49であり、過剰の2-フェニルエタノールはGCにより8.6%であった。反応混合物を50℃まで加熱し、10%w/wの炭酸ナトリウム水溶液125gを加えた。そのバッチを50℃に保持し、15分間攪拌した。攪拌を停止し、該バッチを30分間安定させておいた。水(底)層を、ピペットを用いてフラスコから除去し、活性炭37.3g(0.3%w/w)を加えた。過剰の2-フェニルエタノールを0.5scfhの窒素掃引にて180〜185℃(20torr)で1時間の減圧蒸留により除去した。反応混合物を室温まで冷却し、セライト(登録商標)によってろ過し、安息香酸2-フェニルエチル1030g(83%)を得た(GLCによる純度98.7%):残留アルコール0.66%(GLC);APHA色相89;酸価0.11mgKOH/g;けん化価241mgKOH/g。
塩化ベンゾイルから安息香酸2-フェニルエチルの製造
温度計、機械攪拌機、窒素注入管、及びリービッヒ冷却器/受けフラスコを取り付けた、2Lで四つ首の丸底フラスコに、2-フェニルエタノール244.3g(2.00mol,1.00当量)、トリエチルアミン232.7g(2.30mol,1.15当量)及びトルエン376gを装填した。攪拌速度を約200rpmに設定し、窒素の散布を0.1scfhに設定して、温度を10〜15℃に維持しながら、塩化ベンゾイル286.8g(2.04mol,1.02当量)を1.5時間にわたって添加した。約10℃で更に0.5時間後に氷浴を除去し、反応混合物を室温(23℃)まで温めておいた。室温にて18時間後に、転化率は99%となり、水500gを加えた。50℃で30分間攪拌した後、その相を15分間分離させておいて、水層(底,pH9)をピペットで除去した。有機層を追加の水500gで洗浄し、トルエンを100〜105℃(100torr)でストリッピングした。残留物を170〜172℃(5torr)で蒸留し、安息香酸2-フェニルエチル410g(91%)を得た(GLCによる純度99.2%):残留アルコール0.08%(GLC);APHA色相66;酸価0.57mgKOH/g;けん化価247mgKOH/g;屈折率1.5576;比重1.096。
安息香酸無水物から安息香酸2-フェニルエチルの製造
温度計、機械攪拌機、窒素注入管、及びリービッヒ冷却器/受けフラスコを取り付けた、1Lで四つ首の丸底フラスコに、安息香酸無水物294.1g(1.30mol,1.00当量)、2-フェニルエタノール349.4g(2.86mol,2.20当量)及びFascat2001(登録商標)1.18gを装填した。その系を、全ての安息香酸無水物が溶解するまで、緩徐な攪拌(<50rpm)と共に穏やかに加熱した。機械的真空ポンプ(50〜100torr)を用いる真空排気/窒素充填の3回のサイクルで空気を除去した。攪拌速度を約200rpmまで上昇させ、窒素の散布を0.1scfhに設定し、反応混合物を210℃まで加熱した。210℃で1時間保持した後、留出物の量は24.4gであり、該留出物からアルコール9.5gを分離し、反応混合物に戻した。温度を1時間で220℃まで上昇させ、その間に更に留出物10.8gを集めた。アルコール(3.7g)を分離し、反応混合物に戻した。温度を230℃まで上昇させ、1時間保持した後、更に留出物1.8gを集めたが、アルコール(0.5g)を戻さなかった。酸価は2.15mgKOH/gであった。過剰のアルコールをストリッピングし、通常通り、生成物を活性炭で処理し、安息香酸2-フェニルエチル470g(80%)を得た(GLCによる純度99.4%)。残留アルコールは、GLCにより0.08%であり、APHA色相は426であった。生成物を例3と同様に蒸留し、安息香酸2-フェニルエチル430g(73%)を得た(GLCによる純度99.7%):残留アルコール0.03%(GLC);APHA色相10;酸価0.21mgKOH/g;けん化価244mgKOH/g;屈折率1.5575;比重1.095。
安息香酸2-フェニルエチルの製造(エステル交換)
温度計、機械攪拌機、窒素注入管、及び還流冷却器を取り付けた、1Lで四つ首の丸底フラスコに、安息香酸プロピル492.6g(3.00mol,1.50当量)、2-フェニルエタノール244.3g(2.00mol,1.00当量)、Fascat2001(登録商標)(シュウ酸スズ)2.3g及びFascat(登録商標)4201(ジブチルスズオキシド)2.3gを装填した。攪拌速度を約200rpmに設定し、窒素の散布を0.2scfhに設定し、還流を開始したらすぐに反応混合物を150〜160℃で1時間加熱した。還流冷却器をリービッヒ冷却器/受けフラスコと交換し、0.3scfhの窒素流れにて160℃で30分間、留出物を除去した。温度を170℃まで上昇させ、窒素流れを0.4schfまで上昇させ、蒸留(蒸気温度90〜95℃)を30分間続けた。温度が230℃(30分)になるまで30分毎に温度を10℃ずつ上昇させ、窒素の散布を0.1schfずつ上昇させて、合計119gの留出物を集めた(理論値120g)。過剰の安息香酸プロピルをストリッピングして、生成物を例3と同様に蒸留し、安息香酸2-フェニルエタノール390g(86%)を得た(GLCによる純度99.6%):残留2-フェニルエタノール<0.01%(GLC);残留安息香酸プロピル0.1%(GLC);APHA色相24;酸価0.20mgKOH/g;けん化価245mgKOH/g;屈折率1.5574;比重1.095。
安息香酸1-フェニルエチルの製造
例3の方法により、1-フェニルエタノール及び塩化ベンゾイルから生成物(GLCによる純度98.9%)を製造した:酸価1.44mgKOH/g;けん化価248mgKOH/g;屈折率1.5555;比重1.092。
安息香酸ベンジルの製造
例1の方法により、ベンジルアルコール及び安息香酸から生成物(GLCによる純度99.3%)を製造した:酸価0.37mgKOH/g;けん化価261mgKOH/g;屈折率1.5661;比重1.117。
安息香酸p-メチルベンジルの製造
例1の方法により、p-メチルベンジルアルコール及び安息香酸から生成物(GLCによる純度99.0%)を製造した:酸価0.10mgKOH/g;けん化価239mgKOH/g;屈折率1.5597;比重1.003。
安息香酸3-フェニルプロピルの製造
例1の方法により、3-フェニルプロパノール及び安息香酸から生成物(GLCによる純度99.7%)を製造した:酸価0.19mgKOH/g;けん化価232mgKOH/g;屈折率1.5515;比重1.078。
安息香酸2-フェノキシエチルの製造
例1の方法により、2-フェノキシエタノール及び安息香酸から生成物(GLCによる純度99.4%)を製造した:酸価0.25mgKOH/g;けん化価229mgKOH/g;屈折率1.5608;比重1.157。
安息香酸4-フェニルブチルの製造
例1の方法により、4-フェニルブタノール及び安息香酸から生成物(GLCによる純度99.7%)を製造した:酸価0.05mgKOH/g;けん化価220mgKOH/g;屈折率1.5467;比重1.063。
安息香酸1-フェニルプロピルの製造
例3の方法により、1-フェニルプロパノール及び塩化ベンゾイルから生成物(GLCによる純度98.4%)を製造した:酸価0.96mgKOH/g;けん化価233mgKOH/g;屈折率1.5494;比重1.074。
安息香酸2-(N-ベンジル-N-メチルアミノ)エチルの製造
例5の方法により、2-(N-ベンジル-N-メチルアミノ)エタノール及び安息香酸プロピルから生成物(GLCによる純度98.1%)を製造した:酸価0.65mgKOH/g;けん化価208mgKOH/g;屈折率1.5483;比重1.074。
プロピレングリコールジベンゾエートの製造
例1の方法により、1,2-プロパンジオール(プロピレングリコール)及び安息香酸から生成物(GLCによる純度98.9%)を製造した:酸価3.31mgKOH/g;けん化価388mgKOH/g;屈折率1.5433;比重1.148。
o-アニス酸2-フェニルエチルの製造
例1の方法により、2-フェニルエタノール及びアニス酸から生成物(GLCによる純度97.0%)を製造した:酸価2.96mgKOH/g;けん化価218mgKOH/g;屈折率1.5646;比重1.139。
p-フルオロ安息香酸2-フェニルエチルの製造
例1の方法により、2-フェニルエタノール及びp-フルオロ安息香酸から生成物(GLCによる純度99.2%)を製造した:酸価0.27mgKOH/g;けん化価227mgKOH/g;屈折率1.5425;比重1.158。
o-トルイル酸2-フェニルエチルの製造
例1の方法により、2-フェニルエタノール及びo-トルイル酸から生成物(GLCによる純度97.2%)を製造した:酸価0.01mgKOH/g;けん化価225mgKOH/g;屈折率1.5556;比重1.082。
o-トルイル酸1-フェニルエチルの製造
例3の方法により、1-フェニルエタノール及びo-トルイル酸から生成物(GLCによる純度98.0%)を製造した:酸価0.12mgKOH/g;けん化価231mgKOH/g;屈折率1.5543;比重1.079。
p-トルイル酸2-フェニルエチルの製造
例1の方法により、2-フェニルエタノール及びp-トルイル酸から生成物(GLCによる純度96.1%)を製造した:酸価0.15mgKOH/g;けん化価228mgKOH/g;屈折率1.5547;比重1.074。
p-トルイル酸1-フェニルエチルの製造
例3の方法により、1-フェニルエタノール及びp-トルイル酸から生成物(GLCによる純度98.5%)を製造した:酸価1.50mgKOH/g;けん化価234mgKOH/g;屈折率1.5539;比重1.069。
フェニル酢酸2-フェニルエチルの製造
例1の方法により、2-フェニルエタノール及びフェニル酢酸から生成物(GLCによる純度98.6%)を製造した:酸価0.16mgKOH/g;けん化価231mgKOH/g;屈折率1.5472;比重1.081。
フェニル酢酸1-フェニルエチルの製造
例3の方法により、1-フェニルエタノール及び塩化フェニルアセチルから生成物(GLCによる純度98.6%)を製造した:酸価1.39mgKOH/g;けん化価228mgKOH/g;屈折率1.5434;比重1.073。
フェニル酢酸2-メチル-1-フェニル-2-プロピルの製造
例3の方法により、2-メチル-1-フェニル-2-プロパノール及びフェニル酢酸から生成物(GLCによる純度95.3%,異性体の混合物2:1)を製造した:酸価9.22mgKOH/g;けん化価173mgKOH/g;屈折率1.5438;比重1.053。
2-フェニル酪酸2-フェニルエチルの製造
例1の方法により、2-フェニルエタノール及び2-フェニル酪酸から生成物(GLCによる純度99.7%)を製造した:酸価0.26mgKOH/g;けん化価207mgKOH/g;屈折率1.5351;比重1.047。
α,α,α-トリフルオロ-m-トリル酢酸ベンジルの製造
例1の方法により、ベンジルアルコール及びα,α,α-トリフルオロ-m-トルイル酸から生成物(GLCによる純度99.4%)を製造した:酸価0.07mgKOH/g;けん化価189mgKOH/g;屈折率1.5054;比重1.233。
ヒドロケイ皮酸3-フェニルプロピルの製造
例1の方法により、3-フェニルプロパノール及びヒドロケイ皮酸から生成物(GLCによる純度99.6%)を製造した:酸価0.12mgKOH/g;けん化価206mgKOH/g;屈折率1.5379;比重1.052。
フェノキシ酢酸3-フェニルプロピルの製造
例1の方法により、3-フェニルプロパノール及びフェノキシ酢酸から生成物(GLCによる純度99.5%)を製造した:酸価0.05mgKOH/g;けん化価206mgKOH/g;屈折率1.5454;比重1.111。
マロン酸ジベンジルの製造
例5の方法により、ベンジルアルコール及びマロン酸ジメチルから生成物(GLCによる純度97.9%)を製造した:酸価0.43mgKOH/g;けん化価387mgKOH/g;屈折率1.5415;比重1.161。
種々の溶媒における固体有機日焼け止め剤の溶解度
所定の溶媒−日焼け止め剤の組み合わせを用いて、所定の溶液(w/w)を40〜50℃で調製した。溶液を恒温室に25℃で1週間置いておいた。最初に少量の種結晶を25℃で添加し、平衡化を促進させた。機器を較正するために標準溶液を用いて、GLCにより溶解度を測定した。下記の表1に示すように、本発明の可溶化剤は、少なくとも一種の日焼け止め剤の少なくとも10%、好ましくは20%、最も好ましくは30%以上(w/w)を可溶化するのに有効である。
X-Tend(登録商標)226を有する無水油の日焼け止め剤組成物
SPF=22.8、これは対照の値と比べて有意に高い。
SPF=12.0が測定された。
O/W 乳化日焼け止め剤組成物
水中で混合しながらスタビライズをまく。80℃にてA相を加熱する。混合しながら85℃で45分間維持する。45分後、A相に残りの成分を添加する。別に、B相の成分を合わせて、80℃に加熱し、融解するまで混合する。A相にプロペラで十分に混合しながらB相を添加する。均一になるまで混合する。そのバッチを冷まし始める。70℃でC相(10%NaOH溶液)を加える。40℃でD相成分を加え、十分に混合する。SPF=25.7。
水中で混合しながらスタビライズをまく。80℃にてA相を加熱する。混合しながら85℃で45分間維持する。45分後、A相に残りの成分を添加する。別に、B相の成分を合わせて、80℃に加熱し、融解するまで混合する。A相にプロペラで十分に混合しながらB相を添加する。均一になるまで混合する。そのバッチを冷まし始める。70℃でC相(10%NaOH溶液)を加える。40℃でD相成分を加え、十分に混合する。SPF=22.6。
UVA吸収の増大
10mg分の日焼け止め剤を溶媒1Lに溶解し、紫外線可視分光光度計Cary 1Eを用いて該溶液のUVスペクトルを測定した。表2の結果は、組成物において、C12-15ベンゾエートの代わりに安息香酸2-フェニルエチルを用いる活性日焼け止め剤に大きなUVA防護を与えることを示す。
広域スペクトル UVA/UVB日焼け止め製剤
‘老化防止’製剤(表3)を、5回の凍結融解サイクルの後と、それから45℃で1月の保存の後にオプトメトリーズ(Optometries)SPF290分析器を用いて、UVA防護の尺度である臨界波長について検討した。臨界波長が高ければ高いほど、UVA防護は大きい。凍結融解と1月の保存条件の両方について明らかなように(表4)、X-Tend(登録商標)226(安息香酸2-フェニルエチル)を含有する製剤が、Finsolv(登録商標)TN、Eldew(登録商標)SL-205、Finsolv(登録商標)TPP及びElefac(登録商標)I-305を含有する他の製剤より優れていた。
トリクロサンの溶解度
5-クロロ-2-(2,4-ジクロロフェノキシ)フェノール(トリクロサン)は、静菌性を有しており、化粧品や洗浄剤において殺菌剤や防腐剤として使用される。GLCにより測定すると、安息香酸2-フェニルエチル中69%w/wまで溶解できる。
例35は、抗白化剤として安息香酸2-フェニルエチルを用い、アルミニウムジルコニウムテトラクロロハイドレックスGLYを有する典型的な制汗剤スティック組成物を以下に示す。
成分 %w/w
A相
SI−TEC(登録商標)CM040 42.00
パラフィン 6.50
ステアリルアルコール 15.00
X−Tend(登録商標)226 5.00
B相
ジルコニウム塩 25.00
タルク 5.75
C相
CK−1フレグランス 0.75
合計 100.00%
安息香酸2-フェニルエチル及びアルミニウムクロロヒドレートを
有する制汗剤スティック
成分 %w/w
A相
SI−TEC(登録商標)CM040 42.00
パラフィン 6.50
ステアリルアルコール 15.00
X−Tend(登録商標)226 5.00
B相
アルミニウムクロロヒドレート 25.00
タルク 5.75
C相
CK−1フレグランス 0.75
合計 100.00%
安息香酸2-フェニルエチルを有さず、ジルコニウム塩を有する制汗剤スティック
成分 %w/w
A相
SI−TEC(登録商標)CM040 47.00
パラフィン 6.50
ステアリルアルコール 15.00
B相
ジルコニウム塩 25.00
タルク 5.75
C相
CK−1フレグランス 0.75
合計 100.00%
安息香酸2-フェニルエチルを有さず、アルミニウムクロロヒドレート塩
を有する制汗剤スティック
成分 %w/w
A相
SI−TEC(登録商標)CM040 47.00
パラフィン 6.50
ステアリルアルコール 15.00
B相
アルミニウムクロロヒドレート 25.00
タルク 5.75
C相
CK−1フレグランス 0.75
合計 100.00%
下記の製剤は、高屈折率の性質により光沢を与える安息香酸2-フェニルエチルの能力を目立たせる高い光沢の口紅である。この製剤は、最初に、混練前に着色配合物を添加した融解ガネックス(登録商標)WP-660について、ロールミルを用いて着色粉砕物を調製することにより作製された。A相の成分を均一になるまで90〜95℃に加熱して混合し、82〜85℃に冷やした。それから、B相を加えて、均一になるまで混合した。次に、C相の着色粉砕物を添加し、30分間混合した。最後に、D相の成分を添加し、均一になるまで混合した。その内容物を82〜85℃で口紅のモールド中に注ぎ、凝固させた。唇に塗布すると、鮮やかな光沢と艶のある外観が、使用者の唇から広がった。
成分 %w/w
A相
オゾケライト(白色オゾケライトワックス170) 10.50
ポリエチレン(Performaleneポリマー) 5.00
ステアリン酸オクチルドデシル(セラフィル(登録商標)ODS) 13.00
アジピン酸ジイソプロピル(セラフィル(登録商標)230) 2.00
ステアロイルステアリン酸オクチルドデシル 12.00
(セラフィル(登録商標)847)
安息香酸2−フェニルエチル(X−Tend(登録商標)226) 4.00
乳酸C12−15アルキル(セラフィル(登録商標)41) 11.00
乳酸ミリスチル(セラフィル(登録商標)50) 1.00
水素化ポリイソブテン 6.10
(Panalane L−14E)
VP/エイコセン共重合体(ガネックス(登録商標)V−220) 5.00
VP/ヘキサデセン共重合体(ガネックス(登録商標)V−216) 5.00
ジソジウムラウリミノジプロピオネート 0.20
トコフェリルホスフェイト(バイタル(VITAL)(登録商標)ET)
パルミチン酸レチニル(ビタミンAパルミテート) 0.10
B相
イソプロピルパラベン(及び)イソブチルパラベン(及び)
ブチルパラベン(リカパー(登録商標)オイル) 0.40
C相
ステアロイルステアリン酸イソセチル(セラフィル(登録商標)791) 3.28
トリコンタニルPVP(ガネックス(登録商標)WP−660) 0.07
赤色7号レーキ(C5507 D&C 赤色#7 CA LK) 2.35
酸化鉄(C33−5198 黒色酸化鉄) 0.75
青色1号レーキ(FD&C 青色#1 アルミニウムレーキ) 0.25
D相
マイカ(マイカUF) 8.00
オキシ塩化ビスマス(Pearl Glo UVR) 3.00
マイカ(及び)酸化鉄(Cloisonne Gold) 4.00
マイカ(及び)酸化鉄 3.00
(Cloisonne Super Rouge)
100.00%
製剤中に安息香酸2-フェニルエチルが含まれていない、例37の口紅製剤を調製した。それを使用者の唇に塗布すると、かなりくすんだ外観をもたらした。
製剤は、スイープブレード攪拌を有する適した混合容器に水を装填することにより作製された。スタイリーゼ(登録商標)W-20及びリキッドジャーマル(登録商標)プラスを混合しながら加えて、混合を均一になるまで続けた。次に、安息香酸2-フェニルエチルを添加し、均一になるまで混合した。最後に、Rapi−Thix(登録商標)A-60を添加し、そのバッチを均一になるまで混合した(約15分)。
成分 Wt.%
水 91.55
ポリクオタニウム−55(スタイリーゼ(登録商標))(ISP) 1.25
ポリプロピレングリコール(及び)ジアゾリジニル尿素(及び) 0.50
ブチルカルバミン酸ヨウ化プロピル
(リキッドジャーマル(登録商標)プラス)(ISP)
安息香酸2−フェニルエチル 5.00
(X−Tend(登録商標)226)(ISP)
ポリアクリル酸ナトリウム(及び)水素化ポリデセン(及び) 1.70
トリデセス−6(Rapi−Thix(登録商標)A−60)(ISP)
100.00%
また、安息香酸2-フェニルエチルを有しない例38の製剤を髪に塗布した。くすんだ外観をもたらした。
Claims (3)
- 日焼け止め剤を含有する日焼け止め組成物であって、
該日焼け止め剤は、極性又は分極性官能基を含有するジアリール有機化合物中で可溶化された活性又は官能性有機化合物であり、
前記ジアリール有機化合物は、
- 前記極性基が、エステルであることを特徴とする請求項1に記載の組成物。
- 前記組成物が、増大したSPF及び/又はUVA/UVB吸光度比及び/又は臨界波長を示すことを特徴とした、UVA及び/又はUVB化学化合物を含有する請求項1に記載の組成物。
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US10/952,948 US20060067900A1 (en) | 2004-09-29 | 2004-09-29 | Method and composition for imparting high shine to a polymeric substrate |
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US10/961,564 US7132097B2 (en) | 2004-10-08 | 2004-10-08 | Sunscreen compositions |
US11/007,744 | 2004-12-08 | ||
US11/007,744 US20050152858A1 (en) | 2003-07-11 | 2004-12-08 | Solubilizing agents for active or functional organic compounds |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002505794A (ja) * | 1997-06-13 | 2002-02-19 | ガタン・インコーポレーテッド | 電子顕微鏡の影像検出器の解像度を改良しノイズを低減する方法及び装置 |
Families Citing this family (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050226829A1 (en) * | 2004-04-07 | 2005-10-13 | Inolex Investment Corporation | Personal care products containing high refractive index esters and methods of preparing the same |
US9717931B2 (en) * | 2004-07-02 | 2017-08-01 | L'oreal | Solubilization of triazine UV-screening agents with arylalkyl benzoate compounds/amide-based oils and photoprotective compositions comprised thereof |
FR2872413B1 (fr) * | 2004-07-02 | 2008-06-27 | Oreal | Procede de photostabilisation d'un derive de dibenzoylmethane par un derive arylalkyl benzoate et compositions photoprotectrices |
US7364720B2 (en) * | 2004-07-02 | 2008-04-29 | L'oreal | Photostabilization of dibenzoylmethane UV-screening agents with arylalkyl benzoate compounds/amide-based oils and photoprotective compositions comprised thereof |
US7368105B2 (en) * | 2004-07-02 | 2008-05-06 | L'oreal | Photostabilization of dibenzoylmethane UV-screening agents with arylalkyl benzoate/bis-resorcinyl triazine compounds and photoprotective compositions comprised thereof |
JP4691432B2 (ja) * | 2005-10-31 | 2011-06-01 | 花王株式会社 | 香料組成物 |
WO2008014505A2 (en) * | 2006-07-28 | 2008-01-31 | Isp Investments Inc. | Blends for improved solubilization of active and functional organic compounds |
EP1905483A1 (de) | 2006-09-27 | 2008-04-02 | Cognis IP Management GmbH | Alkylbenzoat Gemische |
WO2010049884A1 (en) * | 2008-10-31 | 2010-05-06 | Firmenich Sa | Flavoured emulsion |
CN102573781A (zh) * | 2009-03-20 | 2012-07-11 | 宝洁公司 | 包含油溶性固体防晒剂的个人护理组合物 |
SG182836A1 (en) * | 2010-02-05 | 2012-09-27 | Phosphagenics Ltd | Carrier composition |
US10071030B2 (en) | 2010-02-05 | 2018-09-11 | Phosphagenics Limited | Carrier comprising non-neutralised tocopheryl phosphate |
EP2685992A4 (en) | 2011-03-15 | 2014-09-10 | Phosphagenics Ltd | AMINO-QUINOLINES AS KINASE INHIBITORS |
KR20140131538A (ko) * | 2012-02-14 | 2014-11-13 | 에메랄드 칼라마 케미칼, 엘엘씨 | 플라스티솔 조성물에서 가소제로서 유용한 모노벤조에이트 |
DE102013213175A1 (de) | 2013-07-04 | 2015-01-08 | Beiersdorf Ag | Sonnenschutzmittel mit hohem Triazingehalt |
ES2797757T3 (es) | 2014-09-26 | 2020-12-03 | Emerald Kalama Chemical Llc | Análogos de monobenzoato útiles como plastificantes en composiciones de plastisol |
US10995198B2 (en) | 2014-09-26 | 2021-05-04 | Emerald Kalama Chemical, Llc | Monobenzoate analogs useful as plasticizers in plastisol compositions |
JP6851327B2 (ja) * | 2015-06-12 | 2021-03-31 | アイエスピー インヴェストメンツ エルエルシー | 機能性活性化合物のための可溶化剤 |
CN114712308A (zh) | 2015-12-09 | 2022-07-08 | 磷肌酸有限公司 | 药物制剂 |
AU2017381395A1 (en) | 2016-12-21 | 2019-06-20 | Phosphagenics Limited | Process |
JP6953160B2 (ja) * | 2017-03-30 | 2021-10-27 | 株式会社コーセー | 口唇化粧料 |
SG11202013057TA (en) * | 2018-06-28 | 2021-01-28 | Emerald Kalama Chemical Llc | Improved reactive polyurethane systems |
CN114430067B (zh) * | 2020-10-29 | 2023-08-22 | 张家港市国泰华荣化工新材料有限公司 | 一种非水锂电池电解液及二次锂电池 |
CA3216096A1 (en) | 2021-06-08 | 2022-12-15 | Entheogenix Biosciences, Inc. | Dimethoxyphenylalkylamine activators of serotonin receptors |
KR20240019152A (ko) | 2021-06-09 | 2024-02-14 | 아타이 테라퓨틱스, 인크. | 신규 전구약물 및 디메틸트립타민의 접합체 |
WO2023009315A1 (en) * | 2021-07-30 | 2023-02-02 | Isp Investments Llc | A sunscreen composition comprising avobenzone and a method for photostabilization |
WO2023129909A1 (en) | 2021-12-27 | 2023-07-06 | ATAI Life Sciences AG | Aminotetraline activators of serotonin receptors |
CA3238440A1 (en) | 2021-12-30 | 2023-07-06 | Atai Therapeutics, Inc. | Dimethyltryptamine analogues as nitric oxide delivery drugs |
CN114105770B (zh) * | 2022-01-25 | 2022-04-15 | 江西中医药大学 | 一种酯类化合物及其制备方法与应用 |
Family Cites Families (72)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1899214A (en) * | 1932-02-10 | 1933-02-28 | Eastman Kodak Co | Cellulose organic ester composition containing phenylethyl benzoate |
US2146894A (en) * | 1935-10-11 | 1939-02-14 | Distillation Products Inc | Vacuum distillation |
US2463264A (en) * | 1942-12-23 | 1949-03-01 | Ciba Ltd | Derivatives of cyclic amidines and process of making same |
GB1103681A (en) * | 1966-01-28 | 1968-02-21 | Geigy Uk Ltd | Chemical compositions |
US3803319A (en) * | 1971-01-04 | 1974-04-09 | L Musajo | Treating hyperlipemia with isatin |
US3755560A (en) * | 1971-06-30 | 1973-08-28 | Dow Chemical Co | Nongreasy cosmetic lotions |
DE2544180C2 (de) * | 1975-10-03 | 1984-02-23 | Merck Patent Gmbh, 6100 Darmstadt | Lichtschutzmittel für kosmetische Zwecke |
SE424962B (sv) * | 1976-08-10 | 1982-08-23 | Malte Sandgren Ab | Pump till sprayflaska |
CH614878A5 (ja) * | 1977-03-11 | 1979-12-28 | Charmilles Sa Ateliers | |
NL190101C (nl) * | 1978-11-13 | 1993-11-01 | Givaudan & Cie Sa | Dibenzoylmethaanverbinding en tegen licht beschermend preparaat. |
US4322545A (en) * | 1979-09-14 | 1982-03-30 | Finetex, Inc. | Benzoic acid esters |
US4421769A (en) * | 1981-09-29 | 1983-12-20 | The Procter & Gamble Company | Skin conditioning composition |
FR2520233A1 (fr) * | 1982-01-28 | 1983-07-29 | Oreal | Composition d'anthraline ou de l'un de ses derives dans un ester aromatique et son utilisation dans le traitement des maladies de la peau |
DE3302123A1 (de) * | 1983-01-22 | 1984-07-26 | Haarmann & Reimer Gmbh | Neue dibenzol-methan-derivate, verfahren zu ihrer herstellung und ihre verwendung |
US4559226A (en) * | 1983-09-06 | 1985-12-17 | Bernel Chemical Company Inc. | Self-emulsifying alkoxylate esters |
JPS61291520A (ja) * | 1985-06-19 | 1986-12-22 | Daigo Eiyou Kagaku Kk | エリスロマイシン脂肪乳剤 |
NL8502651A (nl) * | 1985-09-27 | 1987-04-16 | Airspray Int Bv | Verstuiver voor een houder voor een te verstuiven vloeistof. |
US5192530A (en) * | 1987-01-30 | 1993-03-09 | Colgate-Palmolive Company | Antibacterial antiplaque oral composition |
US4791097A (en) * | 1987-03-09 | 1988-12-13 | Finetex, Inc. | Benzoic acid esters and their use |
JPH082781B2 (ja) * | 1988-10-18 | 1996-01-17 | 嘉明 川島 | 中空顆粒状医薬及びその製法 |
US5186928A (en) * | 1989-02-20 | 1993-02-16 | Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. | Shampoo composition |
US4919934A (en) * | 1989-03-02 | 1990-04-24 | Richardson-Vicks Inc. | Cosmetic sticks |
US4985238A (en) * | 1989-03-14 | 1991-01-15 | The Procter & Gamble Company | Low residue antiperspirant sticks |
JPH02268142A (ja) * | 1989-04-10 | 1990-11-01 | Toubishi Yakuhin Kogyo Kk | 筋弛緩作用を有する新規化合物及びその製造方法 |
US5011681A (en) * | 1989-10-11 | 1991-04-30 | Richardson-Vicks, Inc. | Facial cleansing compositions |
US5073372A (en) * | 1990-11-30 | 1991-12-17 | Richardson-Vicks, Inc. | Leave-on facial emulsion compositions |
US5237071A (en) * | 1991-01-22 | 1993-08-17 | Fairmount Chemical Company, Inc. | Process for preparing 2,2'-methylene-bis(6-(2H-benzotriazol-2-yl)-4-hydrocarbyl phenols) |
US5166355A (en) * | 1991-02-04 | 1992-11-24 | Fairmount Chemical Co., Inc. | Process for preparing substituted 2,2'-methylene-bis-[6-(2H-benzotriazol-2-yl)-4-hydrocarbyl-phenols] |
CA2085892C (en) * | 1991-04-20 | 2002-12-10 | Ahmet E. Baydar | Perfume bases |
US5302381A (en) * | 1992-03-20 | 1994-04-12 | Church & Dwight Co., Inc. | Low residue antiperspirant sticks |
GB9208339D0 (en) * | 1992-04-15 | 1992-06-03 | Unilever Plc | Treatment composition |
US5376362A (en) * | 1992-12-08 | 1994-12-27 | Church & Dwight Co., Inc. | Antiperspirant-deodorant cosmetic products |
US5486355A (en) * | 1992-12-08 | 1996-01-23 | Church & Dwight Co., Inc. | Homogeneous cosmetic stick products |
US5417963A (en) * | 1992-12-08 | 1995-05-23 | Church & Dwight Co., Inc. | Hydrophilic polymer-coated microcrystallites of bicarbonate ingredient |
US5482702A (en) * | 1993-04-27 | 1996-01-09 | Church & Dwight Co., Inc. | Hydrophilic polymer-coated microcrystallites of bicarbonate salt |
US5500209A (en) * | 1994-03-17 | 1996-03-19 | The Mennen Company | Deodorant and antiperspirant compositions containing polyamide gelling agent |
ES2152397T3 (es) * | 1994-03-29 | 2001-02-01 | Procter & Gamble | Composiciones para el bronceado artificial que tienen un desarrollo del color mejorado. |
AU3677995A (en) * | 1994-10-20 | 1996-05-15 | Procter & Gamble Company, The | Personal treatment compositions and/or cosmetic compositions containing enduring perfume |
US5500138A (en) * | 1994-10-20 | 1996-03-19 | The Procter & Gamble Company | Fabric softener compositions with improved environmental impact |
US5618657A (en) * | 1995-02-17 | 1997-04-08 | Eastman Kodak Company | Photographic silver halide element having polyester support and exhibiting improved wet adhesion |
US5733535A (en) * | 1995-10-25 | 1998-03-31 | The Procter & Gamble Co. | Topical compositions containing N-acetylcysteine and odor masking materials |
US6391065B1 (en) * | 1995-11-03 | 2002-05-21 | Boehme Filatex, Inc. | UV light absorber composition and method of improving the lightfastness of dyed textiles |
US5905066A (en) * | 1997-12-09 | 1999-05-18 | Colgate-Palmolive Co. | All purpose carpet cleaning compositions |
US5998120A (en) * | 1997-12-30 | 1999-12-07 | Eastman Kodak Company | Process for making a direct dispersion of a photographically useful material |
DE19820827A1 (de) * | 1998-05-09 | 1999-11-11 | Beiersdorf Ag | Kosmetische und dermatologische Lichtschutzformulierungen mit einem Gehalt an Triazinderivaten und einem oder mehreren Estern verzweigtkettiger Carbonsäuren und verzweigtkettiger Alkohole |
DE19820825A1 (de) * | 1998-05-09 | 1999-11-11 | Beiersdorf Ag | Kosmetische und dermatologische Lichtschutzformulierungen mit einem Gehalt an Triazinderivaten und einem oder mehreren Estern unverzweigtkettiger Carbonsäuren und verzweigtkettiger Alkohole |
US6368607B1 (en) * | 1998-07-24 | 2002-04-09 | Isp Investments Inc. | Product-structurant composition for personal care formulations |
US6423329B1 (en) * | 1999-02-12 | 2002-07-23 | The Procter & Gamble Company | Skin sanitizing compositions |
JP4791634B2 (ja) * | 1999-03-26 | 2011-10-12 | フイルメニツヒ ソシエテ アノニム | 環式化合物およびその芳香性アルコール前駆体としての使用 |
US6171605B1 (en) * | 1999-07-08 | 2001-01-09 | Color Access, Inc. | Self tanning compositions containing DHA and propolis extract |
GB0000313D0 (en) * | 2000-01-10 | 2000-03-01 | Astrazeneca Uk Ltd | Formulation |
US6635775B1 (en) * | 2000-02-04 | 2003-10-21 | Finetex, Inc. | Reduced odor esters and process for producing same |
AR027527A1 (es) * | 2000-02-17 | 2003-04-02 | Ecosmart Technologies Inc | Composiciones pesticidas que contienen aceites vegetales esenciales contra el piojo del cuerpo humano |
US6210658B1 (en) * | 2000-06-12 | 2001-04-03 | The C. P. Hall Corporation | Stable sunscreen composition containing a barium compound, e.g., barium sulfate, a dibenzoylmethane derivative, e.g., butyl methoxydibenzoylmethane (avobenzone), and a methoxycinnamate derivative, e.g., octyl methoxycinnamate |
AR031108A1 (es) * | 2000-06-19 | 2003-09-10 | Colgate Palmolive Co | Un metodo para mejorar la actividad de una sal de aluminio o de aluminio/circonio que contiene especies de aluminio pequenas y grandes, las sales asi obtenidas y los productos antitranspirantes y/o desodorantes preparados con dichas sales mejoradas |
DE10030663A1 (de) * | 2000-06-23 | 2002-01-10 | Merck Patent Gmbh | UV-B-Filter |
DE10030664A1 (de) * | 2000-06-23 | 2002-01-10 | Merck Patent Gmbh | Verfahren zur Herstellung von UV-Filter-Substanzen |
DE10055940A1 (de) * | 2000-11-10 | 2002-05-29 | Bayer Ag | Neue Indanylidenverbindungen |
IL161782A0 (en) * | 2001-11-08 | 2005-11-20 | Sol Gel Technologies Ltd | Compositions containing oils havinga specific gravity higher than the specific gravity of water |
DE10162697A1 (de) * | 2001-12-19 | 2003-07-03 | Cognis Deutschland Gmbh | Kosmetische und/oder pharmazeutische Sonnenschutzmittel |
US6440402B1 (en) * | 2001-12-14 | 2002-08-27 | Avon Products, Inc. | Photostable sunscreen compositions and methods of stabilizing |
US6541659B1 (en) * | 2002-04-02 | 2003-04-01 | National Taiwan Normal University | Process for acyl substitution of anhydride by vanadyl salt catalyst |
EP2368602A1 (en) * | 2003-03-03 | 2011-09-28 | Takasago International Corporation | Deodorant perfume composition comprising essential oils for masking an acid odour |
JO2505B1 (en) * | 2003-03-14 | 2009-10-05 | باير شيرنغ فارما اكتنجيسيلشافت | Pharmacy methods and formulations for obtaining acceptable serum testosterone levels |
US7241775B2 (en) * | 2003-03-24 | 2007-07-10 | Sanofi-Aventis Deutschland Gmbh | Composition, process of making, and medical use of substituted 4-phenyltetrahydroisoquinolines |
US7166275B2 (en) * | 2003-07-11 | 2007-01-23 | Isp Investments Inc. | Compositions containing phenethyl aryl esters as solubilizing agents for active organic compounds |
US7132097B2 (en) * | 2004-10-08 | 2006-11-07 | Isp Investments Inc. | Sunscreen compositions |
US7208143B2 (en) * | 2004-09-29 | 2007-04-24 | Isp Investments Inc. | Antiperspirant compositions |
EP1713432A2 (en) * | 2004-01-14 | 2006-10-25 | Finetex, Inc. | Phenylethyl benzoate for use in cosmetics, toiletries and personal care products |
FR2872413B1 (fr) * | 2004-07-02 | 2008-06-27 | Oreal | Procede de photostabilisation d'un derive de dibenzoylmethane par un derive arylalkyl benzoate et compositions photoprotectrices |
US20060110415A1 (en) * | 2004-11-22 | 2006-05-25 | Bioderm Research | Topical Delivery System for Cosmetic and Pharmaceutical Agents |
CN102202637B (zh) * | 2008-10-31 | 2013-05-22 | 株式会社资生堂 | O/w乳化组合物 |
-
2004
- 2004-12-08 US US11/007,744 patent/US20050152858A1/en not_active Abandoned
-
2005
- 2005-01-10 EP EP05705469A patent/EP1802290A4/en not_active Withdrawn
- 2005-01-10 JP JP2007534560A patent/JP5065029B2/ja active Active
- 2005-01-10 WO PCT/US2005/000825 patent/WO2006041506A2/en active Application Filing
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002505794A (ja) * | 1997-06-13 | 2002-02-19 | ガタン・インコーポレーテッド | 電子顕微鏡の影像検出器の解像度を改良しノイズを低減する方法及び装置 |
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WO2006041506A2 (en) | 2006-04-20 |
WO2006041506A3 (en) | 2007-12-21 |
US20050152858A1 (en) | 2005-07-14 |
EP1802290A2 (en) | 2007-07-04 |
EP1802290A4 (en) | 2009-08-19 |
JP2008514697A (ja) | 2008-05-08 |
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