JP5415755B2 - 酸化防止剤 - Google Patents
酸化防止剤 Download PDFInfo
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- JP5415755B2 JP5415755B2 JP2008506945A JP2008506945A JP5415755B2 JP 5415755 B2 JP5415755 B2 JP 5415755B2 JP 2008506945 A JP2008506945 A JP 2008506945A JP 2008506945 A JP2008506945 A JP 2008506945A JP 5415755 B2 JP5415755 B2 JP 5415755B2
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Description
Xは、基−C(=O)−Z 2 −R 1 であり、
Yは、Hであり、
Z 1 は、単結合であり、
Z 2 は、Oであり、
R 1 は、分岐若しくは非分岐のC 1-30 −アルキル又はヒドロキシアルキル基であり、
R 2 、R 4 及びR 6 は、それぞれ互いに独立に、HまたはOHであり、
R 3 及びR 5 は、それぞれ互いに独立に、直鎖若しくは分岐のC 1-20 −アルコキシ基である。
・好ましい化合物は強い酸化防止作用を高い分子安定性と結びつける、
・化粧品、薬剤、特に皮膚科産物、又は家庭用品、あるいは食品及び食品サプリメントに対する、特に、染料、コンシステンシー物質又は匂い物質を含む産物に対する産物安定化作用、
・式Iaで示される好ましい化合物は、組成物中の油成分として適している、
・式Iaで示される好ましい化合物は、好ましくは例えば結晶性成分用の溶媒としての、優れた溶解性及び溶媒特性を示す、
・良好な皮膚認容性を有する、
・式Iaで示される好ましい化合物は、LSF、SPF、PPD又はIPDのような光防止因子、又はフリーラジカル防止因子の生成又は増強に適している、
・本出願で後述する特にポリエチレングリコール(PEG)又はポリグリセリン(PG)含有乳化剤のような自己酸化性PEG又はPG誘導体への安定化作用、又は、自己酸化性ポリエチレングリコール(PEG)又はポリグリセリン(PG)誘導体の分解産物の損傷作用の低減、
・着色剤、コンシステンシー物質又は匂い物質に対する、酸化防止剤又はビタミン、UVフィルタ、並びに二酸化チタン含有顔料に対する、特に、化粧品、薬剤、特に皮膚科産物、又は家庭用品、あるいは食品及び食品サプリメントにおける安定化作用、
・酸化防止特性を有する本発明の好ましい化合物は、皮膚領域へ美白作用を有するので、色素沈着の制御のために用いることもできる
・直鎖又は分岐C1〜C20−アルコキシ基、特に、エチルヘキシルオキシ基のような長鎖アルコキシ官能基が化合物の脂溶性を増加させる。
・ある場合には、このタイプの化合物は、油成分の形態で、組成物に容易に組み込むことができ、あるいは他の構成成分に対する溶媒として働くことができる。
・2−シアノ−3,3−ジフェニルアクリル酸2−エチルヘキシル(例えばEusolex(登録商標)OCR)、
・3,3’−(1,4−フェニレンジメチレン)ビス(7,7−ジメチル−2−オキソビシクロ[2.2.1]ヘプタ−1−イルメタンスルホン酸及びその塩(例えばMexoryl(登録商標)SX)、及び
・2,4,6−トリアニリノ−(p−カルボ−2’−エチルヘキシル−1’−オキシ)−1,3,5−トリアジン(例えばUvinul(登録商標)T 150)
・2−(4−ジメチルアミノ−2−ヒドロキシベンゾイル)安息香酸ヘキシル(例えばUvinul(登録商標)UVA Plus、BASF製)
などの他の物質。
・2−(2H−ベンゾトリアゾル−2−イル)−4−メチル−6−(2−メチル−3−(1,3,3,3−テトラメチル−1−(トリメチルシリルオキシ)ジシロキサニル)プロピル)フェノール(例えばSilatrizole(登録商標))、
・4,4’−[(6−[4−((1,1−ジメチルエチル)アミノカルボニル)フェニルアミノ]−1,3,5−トリアジン−2,4−ジイル)ジイミノ]ビス(安息香酸)2−エチルヘキシル(例えばUvasorb(登録商標)HEB)、
・α−(トリメチルシリル)−ω−[トリメチルシリル)オキシ]ポリ[オキシ(ジメチル[及び、メチル[2−[p−[2,2−ビス(エトキシカルボニル]ビニル]フェノキシ]−1−メチレンエチル]約6%及びメチル[3−[p−[2,2−ビス(エトキシカルボニル)ビニル]フェノキシ]プロペニル]約1.5%及び(メチル水素0.1〜0.4%]シリレン]](n≒60)(CAS No.207 574−74−1)
・2,2’−メチレンビス(6−(2H−ベンゾチアゾール−2−イル)−4−(1,1,3,3−テトラメチルブチル)フェノール)(CAS No.103 597−45−1)
・2,2’−(1,4−フェニレン)ビス(1H−ベンズイミダゾール−4,6−ジスルホン酸、一ナトリウム塩)(CAS No.180 898−37−7)及び
・2,4−ビス{[4−(2−エチルヘキシロキシ)−2−ヒドロキシ]フェニル}−6−(4−メトキシフェニル)−1,3,5−トリアジン(CAS No.103 597−45−、187 393−00−6)
・4,4’−[(6−[4−((1,1−ジメチルエチル)アミノカルボニル)フェニルアミノ]−1,3,5−トリアジン−2,4−ジイル)ジイミノ]ビス(安息香酸)2−エチルヘキシル(例えば、Uvasorb(登録商標)HEB)
である。
・鉱油、ミネラルワックス;
・油、例えばカプリン酸又はカプリル酸のトリグリセリド、さらに、天然油、例えば、ヒマシ油;
・油脂、ワックス及び他の天然及び合成脂肪物質、好ましくは、脂肪酸と低炭素数のアルコールとの、例えばイソプロパノール、プロピレングリコール又はグリセロールとのエステル、又は脂肪アルコールと低炭素数のアルカン酸との若しくは脂肪酸とのエステル;
・シリコーン油、例えばジメチルポリシロキサン、ジエチルポリシロキサン、ジフェニルポリシロキサン及びそれらの混合形態のもの。
4−ヒドロキシ−3,5−ジメトキシベンジルマロン酸ジエチル、
3,5−ジメトキシベンジルマロン酸ジ2−エチルヘキシル、
3,5−ジメトキシベンジルマロン酸ジエチル、
図1は、UV光で照射した時の4−ヒドロキシ−3,5−ジメトキシベンジルマロン酸ジ−2−エチルヘキシル(実施例1より)のUVスペクトルにおける変化を示す。
図2は、UV光で照射した時(実施例2を参照)の、β−カロチン0.5重量%及び4−ヒドロキシ−3,5−ジメトキシベンジルマロン酸ジ−2−エチルヘキシル4重量%を含むエマルジョン(曲線A及びB)の、β−カロチン0.5重量%を含むが4−ヒドロキシ−3,5−ジメトキシベンジルマロン酸ジ−2−エチルヘキシルは含まないエマルジョン(曲線C及びD)と比較した、UV/VISスペクトルにおける変化を示す。
例えば、2,2−ジフェニル−1−ピクリルヒドラジル(DPPH)アッセイにより、フリーラジカル減少作用を示すことができる。2,2−ジフェニル−1−ピクリルヒドラジルは、溶液中で安定なフリーラジカルである。不対電子により、515nmに強力な吸収バンドが得られ、溶液は暗紫色である。フリーラジカル捕捉剤の存在下に、電子が対を形成し、吸収が消失し、電子の取り込みにより化学量論的に脱色が進行する。光度計にて吸収を測定する。被試験物質の抗フリーラジカル特性を、用いた2,2−ジフェニル−1−ピクリルヒドラジルの50%がフリーラジカル捕捉剤と反応した濃度を測定することにより決める。この濃度をEC50として表す。この値は、所定の測定条件下における物質の特性であると見なされる。調べられた物質は、標準(例えば、トロフェロール)と比較される。ここで、EC50値は、それぞれの化合物がフリーラジカルを捕捉する性能の目安である。EC50値が低いほど、フリーラジカルを捕捉する性能が高い。
エタノール中に2,2−ジフェニル−1−ピクリルヒドラジル(DPPH)を含む原液を調製する(DPPHフリーラジカル0.025g/l)。試験すべき種々の濃度の化合物を、少量のこの溶液に加える。それぞれの場合、吸収を、515nm、25℃及び1cmで測定する。
実施例1又は参考例1の化合物を含む化粧組成物の例示的調製を以下に示す。対応する化合物を、本発明の全ての化合物を用いて、同様にして製造することができる。
水(EUでは:Aqua)、メトキシ桂皮酸エチルヘキシル、シリカ、PVP、クロルフェネシン、BHT;この組成物は、Merck KGaA,Darmstadtから、Eusolex(登録商標)UV PearlTMOMCの名称で市販されている。
Claims (14)
- 前記式Iaにおいて、R3及びR5が、それぞれ互いに独立に、直鎖又は分岐のC1−4−アルコキシル基であり、R2及びR6が、それぞれ互いに独立に、H又はOHであり、かつR4がOHである、請求項1に記載の式Iaで表される化合物。
- 前記式Iaにおいて、R1が、分岐若しくは非分岐のC7−30−アルキル基又は分岐若しくは非分岐のC6−30−ヒドロキシアルキル基である、請求項1に記載の式Iaで表される化合物。
- 前記式Iaにおいて、2個のR1が同じである、請求項1に記載の式Iaで表される化合物。
- 前記R3及びR5が、それぞれ互いに独立に、メトキシ、イソプロポキシ又はt−ブトキシ基である、請求項2に記載の式Iaで表される化合物。
- 前記式Iaにおいて、R1が分岐又は非分岐C1−30−アルキル基であり、R4がOHである、請求項1に記載の式Iaで表される化合物。
- 4−ヒドロキシ−3,5−ジメトキシベンジルマロン酸ジ2−エチルへキシルである、請求項1に記載の式Iaで表される化合物。
- 4−ヒドロキシ−3,5−ジメトキシベンジルマロン酸ジエチルである、請求項1に記載の化学式Iaで表される化合物。
- 少なくとも1種の請求項1に記載の式1aで表される化合物と、化粧品、薬剤、皮膚科組成物、食品若しくは食品サプリメント又は家庭用品の組成物のために適当な賦形剤を含む化粧品、薬剤、皮膚科薬剤、食品若しくは食品サプリメント又は家庭用品の組成物。
- 前記式Iaで表される化合物を0.01〜20質量%の量で含む、請求項9に記載の組成物。
- 前記組成物が、さらに、ビタミンAパルミチン酸、レチノール、アスコルビン酸、アスコルビン酸パルミテート、マグネシウムアスコルビン酸ホスフェート、アスコルビン酸アセテート、DL−α−トロフェロール、トコフェロールE酢酸、ニコチン酸、パントテン酸及びビオチンからなる群より選ばれる少なくとも1種をふくむ、請求項9に記載の組成物。
- 前記共成分が、3炭糖、4炭糖及び1,3−ジヒドロキシアセトンから選ばれる少なくとも1種のセルフタンニンニング剤を含む、請求項9に記載の組成物。
- 請求項1に記載の式Iaで示される化合物の、有機若しくは無機染料、酸化防止剤、ビタミン、香料成分、油成分、乳化剤、増粘剤、フィルム形成剤又は界面活性剤の保護のための使用。
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DE102005018184A DE102005018184A1 (de) | 2005-04-19 | 2005-04-19 | Antioxidantien |
DE102005018184.8 | 2005-04-19 | ||
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EP05025917 | 2005-11-28 | ||
PCT/EP2006/002592 WO2006111233A1 (de) | 2005-04-19 | 2006-03-21 | Antioxidantien |
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- 2006-03-21 EP EP06742521A patent/EP1871339A1/de not_active Withdrawn
- 2006-03-21 CN CN2006800133011A patent/CN101163659B/zh active Active
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EP1871735B1 (de) | 2015-12-23 |
ES2568516T3 (es) | 2016-04-29 |
JP2008539167A (ja) | 2008-11-13 |
WO2006111233A1 (de) | 2006-10-26 |
EP1871735A1 (de) | 2008-01-02 |
JP2008538381A (ja) | 2008-10-23 |
CN101203278A (zh) | 2008-06-18 |
US20080171004A1 (en) | 2008-07-17 |
CN101163659B (zh) | 2012-09-05 |
CN101163659A (zh) | 2008-04-16 |
EP1871339A1 (de) | 2008-01-02 |
US8106233B2 (en) | 2012-01-31 |
US8268293B2 (en) | 2012-09-18 |
US20080152603A1 (en) | 2008-06-26 |
WO2006111234A1 (de) | 2006-10-26 |
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