JP6265894B2 - ヒドロキシルおよびエーテル官能基からなる特定の極性基を含むメロシアニン誘導体を含有する化粧品および/または皮膚科学的組成物 - Google Patents
ヒドロキシルおよびエーテル官能基からなる特定の極性基を含むメロシアニン誘導体を含有する化粧品および/または皮膚科学的組成物 Download PDFInfo
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- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/18—Antioxidants, e.g. antiradicals
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/41—Particular ingredients further characterized by their size
- A61K2800/413—Nanosized, i.e. having sizes below 100 nm
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/82—Preparation or application process involves sonication or ultrasonication
-
- 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
- A61Q19/04—Preparations for care of the skin for chemically tanning the skin
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Description
R3は、-(C=O)OR6基または-(CO)NHR6基であり、
R6は、1つまたは複数のOHで置換されていてもよいC1〜C22アルキル、C2〜C22アルケニル、C2〜C22アルキニル、C3〜C22シクロアルキルまたはC3〜C22シクロアルケニルであり、
R4およびR5は、水素であるか、または、R4およびR5は、C1〜C4アルキルで置換および/または1つもしくは複数の-O-もしくは-NH-で中断されていてもよい-(CH2)n-環を形成し、
nは、2〜7の数であり、
R7およびR8は、互いに独立して、水素であるか、1つもしくは複数のOで中断および/または1つもしくは複数のOH、C3〜C22シクロアルキルもしくはC3〜C22シクロアルケニルで置換されていてもよいC1〜C22アルキル、C2〜C22アルケニルもしくはC2〜C22アルキニルであり、前記C3〜C22シクロアルキルもしくはC3〜C22シクロアルケニル1つもしくは複数の-O-で中断されていてもよく、
あるいは、R7およびR8は、それらが結合している窒素原子と一緒に、1つまたは複数の-O-で中断されていてもよい-(CH2)n-環を形成し、
R9およびR10は、水素であるか、または、R9およびR10は、C1〜C4アルキルで置換および/または-O-もしくは-NH-で中断されていてもよい-(CH2)n-環を形成し、
Aは、-O-または-NHであり、
R11は、1つもしくは複数のOで中断されていてもよいC1〜C22アルキル、C2〜C22アルケニル、C2〜C22アルキニル、C3〜C22シクロアルキルもしくはC3〜C22シクロアルケニルであるか、または、C3〜C22シクロアルキルもしくはC3〜C22シクロアルケニルで置換されているC1〜C22アルキルもしくはC2〜C22アルケニルであり、前記C3〜C22シクロアルキルもしくはC3〜C22シクロアルケニルは、1つもしくは複数の-O-で中断されていてもよく、
但し、
(I)R1、R2およびR6の少なくとも1つは、ヒドロキシで置換されており、
(II)R1の1つがヒドロキシエチルである場合、R2は、水素、メチル、エチルまたはヒドロキシエチルではなく、R1が水素である場合、R2は、1-ヒドロキシ-3-メチル-ブタ-2-イルではなく、
(III)R6が1つまたは複数のOHで置換されている場合、R1およびR2の1つは、C4〜C22アルキルであるか、またはR1およびR2は、連結している窒素と一緒に、ピペリジル基またはモルホリニル基を形成し、
(IV)R7およびR8の少なくとも1つ、またはR11は、1つまたは複数の-O-で中断されている]
に相当する。
R3が、-(C=O)OR6基または-(CO)NHR6基であり、
R6が、1つまたは複数のOHで置換されていてもよいC1〜C22アルキル、C2〜C22アルケニル、C2〜C22アルキニル、C3〜C22シクロアルキルまたはC3〜C22シクロアルケニルであり、
R4およびR5が、水素であるか、または、R4およびR5が、C1〜C4アルキルで置換および/または-O-もしくは-NH-で中断されていてもよい-(CH2)n-環を形成し、
nが、2〜7の数であり、
R7およびR8が、互いに独立して、水素であるか、1つもしくは複数のOで中断および/または1つまたは複数のOHで置換されていてもよいC1〜C22アルキル、C2〜C22アルケニルもしくはC2〜C22アルキニルであるか、または、R7およびR8が、それらを連結している窒素原子と一緒に、1つまたは複数の-O-で中断されていてもよい-(CH2)n-環を形成し、
R9およびR10が、水素であるか、またはR9およびR10が、C1〜C4アルキルで置換および/または-O-もしくは-NH-で中断されていてもよい-(CH2)n-環を形成し、
Aが、-O-または-NHであり、
R11が、1つまたは複数のOで中断されていてもよいC1〜C22アルキル、C2〜C22アルケニル、C2〜C22アルキニル、C3〜C22シクロアルキル、またはC3〜C22シクロアルケニルであり、
但し、
(I)R1、R2およびR6の少なくとも1つが、ヒドロキシで置換されており、
(II)R1の1つがヒドロキシエチルである場合、R2は、水素、メチル、エチルまたはヒドロキシエチルではなく、R1が水素である場合、R2は、1-ヒドロキシ-3-メチル-ブタ-2-イルではなく、
(III)R6が1つまたは複数のOHで置換されている場合、R1およびR2の1つが、C4〜C22アルキルであるか、またはR1およびR2が、連結している窒素と一緒に、ピペリジル基またはモルホリニル基を形成し、
(IV)R7およびR8の少なくとも1つ、またはR11が、1つまたは複数の-O-で中断されている、
式(1)または(2)の化合物が好ましい。
R3、R4およびR5が、請求項1に定義される通りである、
式(1)または(2)の化合物が好ましい。
式(1)の化合物も好ましい。
R6が、1つまたは複数のヒドロキシで置換されているC1〜C12アルキルであり、
R1およびR2の1つが、C4〜C22アルキルであるか、またはR1およびR2が、それらが連結している窒素原子と一緒に、-O-および/または-NH-で中断置換されていてもよい-(CH2)n-環を形成し、
R4、R5およびnが、請求項1に定義される通りである、
式(1)の化合物がより好ましい。
R12は、C1〜C12アルキル、またはC1〜C6アルコキシ-C1〜C6アルキルであり、
mは、1〜5の数である)であり、
R7、R8、R9、R10およびAが、請求項1に定義される通りである、
式(2)の化合物が好ましい。
式(1)または(2)の化合物がさらに好ましい。
式(1)および(2)の化合物が好ましい。
R3が、-(C=O)OR6基または-(CO)NHR6基であり、
R6が、1つまたは複数の-OHで置換されていてもよいC1〜C22アルキルであり、
R4およびR5が、水素であるか、またはR4およびR5が、一緒に連結して6個の炭素原子を含有する炭素環式環を形成する、
式(1)の化合物が最も好ましい。
R3が、-(C=O)OR6基または-(C=O)NHR6基であり、
R6が、C1〜C22アルキルであり、
R4およびR5が、水素であるか、またはR4およびR5が、一緒に連結して6個の炭素原子を含有する炭素環式環を形成する、
式(1)の化合物が最も好ましい。
Aが、-O-または-NHであり、
R11が、C1〜C22アルキルであり、
R9およびR10が、水素であるか、またはR9およびR10が、一緒に連結して6個の炭素原子を含有する炭素環式環を形成する、
式(2)の化合物が最も好ましい。
Aが、-O-または-NHであり、
R11が、1つまたは複数の-O-で中断されているC1〜C22アルキルであり、
R9およびR10が、水素であるか、またはR9およびR10が、一緒に連結して6個の炭素原子を含有する炭素環式環を形成する、
式(2)の化合物が最も好ましい。
mは、1〜3の数である)であり、
R7およびR8が、互いに独立して、水素であるか、1つもしくは複数のOで中断されていてもよいC1〜C12アルキルであるか、または、R7およびR8が、窒素原子と一緒に、モルホリニルまたはピペリジル基を形成し、
R9およびR10が、水素であるか、または、6個の炭素原子を含有する炭素環式環を形成し、
Aが、-O-または-NHである、
式(2)の化合物がよりさらに好ましい。
エタノール/水の1/1混合物中、0.5%の濃度で、2カ月間、45℃で経過させた後の化学的安定性が良好であり、黄色の着色が少ないこと、
を有することを見出した。
R'3は、-(C=O)OR'6基または-(CO)NHR'6基であり、
R'6は、1つまたは複数のOHで置換されていてもよいC1〜C22アルキル、C2〜C22アルケニル、C2〜C22アルキニル、C3〜C22シクロアルキル、またはC3〜C22シクロアルケニルであり、
R'4およびR'5は、水素であるか、または、R'4およびR'5が、C1〜C4アルキルで置換および/または-O-もしくは-NH-で中断されていてもよい-(CH2)n-環を形成し、
nは、2〜7の数であり、
R'7およびR'8は、互いに独立して、水素であるか、1つもしくは複数のOで中断および/または1つもしくは複数のOHで置換されていてもよいC1〜C22アルキル、C2〜C22アルケニル、もしくはC2〜C22アルキニルであるか、あるいは、R'7およびR'8は、それらを連結している窒素原子と一緒に、-O-で中断されていてもよい-(CH2)n-環を形成し、
R'9およびR'10は、水素であるか、あるいは、R'9およびR'10は、C1〜C4アルキルで置換および/または-O-もしくは-NH-で中断されていてもよい-(CH2)n-環を形成し、
Aは、-O-または-NHであり、
R'11は、1つまたは複数のOで中断されていてもよいC1〜C22アルキル、C2〜C22アルケニル、C2〜C22アルキニル、C3〜C22シクロアルキル、またはC3〜C22シクロアルケニルである]
のメロシアニンは、特にボディケア製品を光分解および酸化分解から防護するのに好適である。
ジベンゾイルメタン誘導体:
ブチルメトキシジベンゾイルメタン(商品名Parsol 1789でDSM Nutritional Productsより販売)。
PABA、
エチルPABA、
エチルジヒドロキシプロピルPABA、
エチルヘキシルジメチルPABA(特に名称Escalol 507でISPより販売)、
グリセリルPABA、
PEG-25 PABA(名称Uvinul P25でBASFより販売)。
ホモサラート(名称Eusolex HMSでMerckより販売)、
エチルヘキシルサリチラート(名称Neo Heliopan OSでSymriseより販売)、
ジプロピレングリコールサリチラート(名称DipsalでLubrizolより販売)、
TEAサリチラート(名称Neo Heliopan TSでSymriseより販売)。
エチルヘキシルメトキシシンナマート(特に商品名Parsol MCXでDSM Nutritional Productsより販売)、
イソプロピルメトキシシンナマート、
イソアミルメトキシシンナマート(商品名Neo Heliopan E 1000でSymriseより販売)、
シノキサート、
DEAメトキシシンナマート、
ジイソプロピルメチルシンナマート、
グリセリルエチルヘキサノアートジメトキシシンナマート。
オクトクリレン(特に、商品名Uvinul N539でBASFより販売)、
エクトクリレン(特に、商品名Uvinul N35でBASFより販売)。
ベンゾフェノン-1(商品名Uvinul 400でBASFより販売)、
ベンゾフェノン-2(商品名Uvinul D50でBASFより販売)、
ベンゾフェノン-3、即ちオキシベンゾン(商品名Uvinul M40でBASFより販売)、
ベンゾフェノン-4(商品名Uvinul MS40でBASFより販売)、
ベンゾフェノン-5、
ベンゾフェノン-6(商品名Helisorb 11でNorquayより販売)、
ベンゾフェノン-8(商品名Cyasorb UV-24でCytecより販売)、
ベンゾフェノン-9(商品名Uvinul DS-49でBASFより販売)、
ベンゾフェノン-12、
n-ヘキシル2-(4-ジエチルアミノ-2-ヒドロキシベンゾイル)ベンゾアート(商品名Uvinul A+で、またはオクチルメトキシシンナマートとの混合物として商品名Uvinul A+Bで、BASFより販売)、
1,1'-(1,4-ピペラジンジイル)ビス[1-[2-[4-(ジエチルアミノ)-2-ヒドロキシベンゾイル]フェニル]メタノン(CAS 919803-06-8)。
3-ベンジリデンカンファー(名称Mexoryl SDでChimexより製造)、
4-メチルベンジリデンカンファー(名称Eusolex 6300でMerckより販売)、
ベンジリデンカンファースルホン酸(名称Mexoryl SLでChimexより製造)、
カンファーベンザルコニウムメトサルファート(名称Mexoryl SOでChimexより製造)、
テレフタリリデンジカンファースルホン酸(名称Mexoryl SXでChimexより製造)、
ポリアクリルアミドメチルベンジリデンカンファー(名称Mexoryl SWでChimexより製造)。
フェニルベンズイミダゾールスルホン酸(特に、商品名Eusolex 232でMerckより販売)、
ジナトリウムフェニルジベンズイミダゾールテトラスルホナート(商品名Neo Heliopan APでSymriseより販売)。
ドロメトリゾールトリシロキサン(商品名SilatrizoleでRhodia Chimieより販売)、
メチレンビス(ベンゾトリアゾリル)テトラメチルブチルフェノール(固体形態で商品名MIXXIM BB/100でFairmount Chemicalより販売、または、微粒子化形態の水性分散液として商品名Tinosorb MでBASFより販売)。
ビス(エチルヘキシルオキシフェノール)メトキシフェニルトリアジン(商品名Tinosorb SでBASFより販売)、
エチルヘキシルトリアゾン(特に、商品名Uvinul T150でBASFより販売)、
ジエチルヘキシルブタミドトリアゾン(商品名Uvasorb HEBでSigma 3Vより販売)、
2つのアミノベンゾアート基で置換されたシリコーントリアジン、例えば、特許EP0841341に開示されているもの、特に、化合物2,4-ビス(n-ブチル4'-アミノベンザルマロナート)-6-[(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)アミノ]-s-トリアジン、
2,4,6-トリス(ジイソブチル4'-アミノベンザルマロナート)-s-トリアジン、
2,4,6-トリス(ジネオペンチル4'-アミノベンザルマロナート)-s-トリアジン、
2,4-ビス(ジネオペンチル4'-アミノベンザルマロナート)-6-(n-ブチル4'-アミノベンゾアート)-s-トリアジン、
対称トリアジン遮蔽剤[特許US6225467、特許出願WO2004/085412 (化合物6および9参照)または文献「Symmetrical Triazine Derivatives」IP.COM Journal、IP.COM INC West Henrietta、NY、US (2004年9月20日)に記載]、特に2,4,6-トリス(ビフェニル)-1,3,5-トリアジン(特に、2,4,6-トリス(ビフェニル-4-イル-1,3,5-トリアジン)、および2,4,6-トリス(ターフェニル)-1,3,5-トリアジン(Beiersdorfの特許出願WO06/035000、WO06/034982、WO06/034991、WO06/035007、WO2006/034992およびWO2006/034985にも記載)。
メンチルアントラニラート(商品名Neo Heliopan MAでSymriseより販売)。
エチルヘキシルジメトキシベンジリデンジオキソイミダゾリンプロピオナート。
ジネオペンチル4'-メトキシベンザルマロナート、
ベンザルマロナート官能基を含有するポリオルガノシロキサン、例えば、ポリシリコーン-15(商品名Parsol SLXでDSM Nutritional Productsより販売)。
1,1-ジカルボキシ(2,2'-ジメチルプロピル)-4,4-ジフェニルブタジエン。
2,4-ビス[5-1(ジメチルプロピル)ベンゾオキサゾール-2-イル-(4-フェニル)イミノ]-6-(2-エチルヘキシル)イミノ-1,3,5-トリアジンおよびその混合物。
エチルヘキシルメトキシシンナマート、
ホモサラート、
エチルヘキシルサリチラート、
オクトクリレン、
ブチルメトキシジベンゾイルメタン、
テレフタリリデンジカンファースルホン酸、
ジナトリウムフェニルジベンズイミダゾールテトラスルホナート、
フェニルベンズイミダゾールスルホン酸、
ベンゾフェノン-3、
n-ヘキシル2-(4-ジエチルアミノ-2-ヒドロキシベンゾイル)ベンゾアート、
4-メチルベンジリデンカンファー、
エチルヘキシルトリアゾン、
ビス(エチルヘキシルオキシフェノール)メトキシフェニルトリアジン、
ジエチルヘキシルブタミドトリアゾン、
2,4-ビス(n-ブチル4'-アミノベンザルマロナート)-6-[(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)アミノ]-s-トリアジン、
2,4,6-トリス(ビフェニル-4-イル-1,3,5-トリアジン、
2,4,6-トリス(ジネオペンチル4'-アミノベンザルマロナート)-s-トリアジン、
2,4,6-トリス(ジイソブチル4'-アミノベンザルマロナート)-s-トリアジン、
2,4-ビス(ジネオペンチル4'-アミノベンザルマロナート)-6-(n-ブチル4'-アミノベンゾアート)-s-トリアジン、
メチレンビス(ベンゾトリアゾリル)テトラメチルブチルフェノール、
ドロメトリゾールトリシロキサン、
ポリシリコーン-15、
ジネオペンチル4'-メトキシベンザルマロナート、
1,1-ジカルボキシ(2,2'-ジメチルプロピル)-4,4-ジフェニルブタジエン、
2,4-ビス[5-1(ジメチルプロピル)ベンゾオキサゾール-2-イル-(4-フェニル)イミノ]-6-(2-エチルヘキシル)イミノ-1,3,5-トリアジンおよびその混合物。
-シリカ、例えば、Ikeda社のSunveilおよびMerck社のEusolex T-AVO、
-シリカおよび酸化鉄、例えば、Ikeda社のSunveil F、
-シリカおよびアルミナ、例えば、Tayca社製のMicrotitanium Dioxide MT500SAおよびMicrotitanium Dioxide MT100SA、CRODA社製のTioveil、ならびにRhodia社製のMirasun TiW 60、
-アルミナ、例えば、Ishihara社製のTipaque TTO-55(B)およびTipaque TTO-55(A)、ならびにKemira社製のUVT14/4、
-アルミナおよびステアリン酸アルミニウム、例えば、Tayca社製のMicrotitanium Dioxide MT100TV、MT100TX、MT100ZおよびMT-01、Croda社製のSolaveil CT-10WおよびSolaveil CT 100、およびSolaveil CT 200、
-アルミナおよびステアリン酸アルミニウム、例えば、Tayca社製のMicrotitanium Dioxide MT100TV、MT100TX、MT100ZおよびMT-01、ならびにCroda社製のSolaveil CT-10W、Solaveil CT 100、およびSolaveil CT 200、
-シリカ、アルミナおよびアルギン酸、例えば、Tayca社製のMT-100AQ、
-アルミナおよびラウリン酸アルミニウム、例えばTayca社製のMicrotitanium Dioxide MT 100 S、
-酸化鉄およびステアリン酸鉄、例えば、Tayca社製のMicrotitanium Dioxide MT100F、
-酸化亜鉛およびステアリン酸亜鉛、例えば、Tayca社製のBR351、
-シリカおよびアルミナでの被覆と、シリコーンでの処理、例えば、Tayca社製のMicrotitanium MT 600 SAS、Microtitanium Dioxide MT 500 SASまたはMicrotitanium Dioxide MT 100 SAS、
-シリカ、アルミナおよびステアリン酸アルミニウムでの被覆とシリコーンによる処理、例えば、Titan Kogyo社製のSTT-30-DS、
-シリカでの被覆とシリコーンでの処理、例えば、Sachtleben社製のUV-Titan M 195、またはTayca社製のSMT-100 WRS、
-アルミナでの被覆と、シリコーンでの処理、例えば、Ishihara社製のTipaque TTO-55 (S)、またはSachtleben社製のUV Titan M 262、
-トリエタノールアミン、例えば、Titan Kogyo社製のSTT-65-S、
-ステアリン酸、例えば、Ishihara社製のTipaque TTO-55 (C)、
-ヘキサメタリン酸ナトリウム、例えば、Tayca社製のMicrotitanium Dioxide MT 150 W、
-オクチルトリメチルシランでの処理、例えば、EVONIK社製の<<T805>>、
-ポリジメチルシロキサン、例えば、CARDRE社製の<<70250 Cardre UF Ti02SI3>>、
-ポリジメチルヒドロゲノシロキサンで処理されたアナターゼ/ルチルTiO2、例えば、COLOR TECHNIQUES社製の<<MICRO TITANIUM DIOXIDE USP GRADE HYDROPHOBIC>>。
-名称Z-CoteでSunsmart社より販売されている顔料、
-名称NanoxでElementisより販売されている顔料、
-名称Nanogard WCD 2025でNanophase Technologies社より販売されている顔料
である。
-名称Z-Cote HP1でSunsmart社より販売されている顔料(ジメチコン被覆ZnO)、
-名称Zinc Oxide CS-5でToshibi社より販売されている顔料(ポリメチルヒドロシロキサンで被覆されたZnO)、
-名称Nanogard Zinc Oxide FNでNanophase Technologies社より販売されている顔料(Finsolv TN、C12〜C15アルキルベンゾアート中の40%分散液)、
-名称Daitopersion ZN-30およびDaitopersion ZN-50でDaito社より販売されている顔料(シリカおよびポリメチルヒドロシロキサンで被覆されたナノ酸化亜鉛を30%または50%含有する、シクロポリメチルシロキサン/オキシエチレン化ポリジメチルシロキサン中の分散液)、
-名称NFD Ultrafine ZnOでDaikin社より販売されている顔料(パーフルオロアルキルホスファートおよびパーフルオロアルキルエチルをベースとするコポリマーで被覆されたZnOのシクロペンタシロキサン中の分散液)、
-名称SPD-Z1でShin-Etsu社より販売されている顔料(シリコーン-グラフトアクリルポリマーで被覆したZnOのシクロジメチルシロキサン中の分散液)、
-名称Escalol Z100でISP社により販売されている顔料(アルミナ処理ZnOの、エチルヘキシルメトキシシンナマート/PVP-ヘキサデセン/メチコンコポリマー混合物中の分散液)、
-名称Fuji ZnO-SMS-10でFuji Pigment社より販売されている顔料(シリカおよびポリメチルシルセスキオキサンで被覆したZnO)、
-名称Nanox Gel TNでElementis社より販売されている顔料(ZnOの、C12〜C15アルキルベンゾアートとヒドロキシステアリン酸の重縮合物中55%濃度の分散液)
である。
- 2-メチルジベンゾイルメタン、
- 4-メチルジベンゾイルメタン、
- 4-イソプロピルジベンゾイルメタン、
- 4-tert-ブチルジベンゾイルメタン、
- 2,4-ジメチルジベンゾイルメタン、
- 2,5-ジメチルジベンゾイルメタン、
- 4,4'-ジイソプロピルジベンゾイルメタン、
- 4,4'-ジメトキシジベンゾイルメタン、
- 4-tert-ブチル-4'-メトキシジベンゾイルメタン、
- 2-メチル-5-イソプロピル-4'-メトキシジベンゾイルメタン、
- 2-メチル-5-tert-ブチル-4'-メトキシジベンゾイルメタン、
- 2,4-ジメチル-4'-メトキシジベンゾイルメタン、
- 2,6-ジメチル-4-tert-ブチル-4'メトキシジベンゾイルメタン。
-R1は、水素原子、または直鎖C1〜C20もしくは分岐C3〜C20アルキル基を示し、
-R2は、C5〜C6環を含有し得る直鎖C1〜C20もしくは分岐C3〜C20アルキル基、1つもしくは2つのメチル基で置換されていてもよいC5〜C6シクロアルキル基、フェニル基、ベンジル基またはフェネチル基を示す。
-R3およびR4は、互いに独立して、水素原子、または直鎖C1〜C12もしくは分岐C3〜C12アルキル基を示す)
の4-カルボキシ-2-ピロリジノンエステル誘導体単独、またはその混合物、および/または塩、および/または異性体、および/または溶媒和物であり、
R1=Hのとき、化合物は、その遊離酸形態であっても、またはその化粧的に許容される塩形態であってもよいことが理解される。
ShinEtsu社より、以下の名称で販売されている製品:
-KSG-21(活性材料中27%、INCI名:ジメチコン/PEG-10ジメチコンビニルジメチコンクロスポリマー)、
-KSG-20(活性材料中95%、INCI名:PEG-10ジメチコンクロスポリマー)、
-KSG-30(活性材料中100%、INCI名:ラウリルPEG-15ジメチコンビニルジメチコンクロスポリマー)、
-KSG-31(活性材料中25%、INCI名:ラウリルPEG-15ジメチコンビニルジメチコンクロスポリマー)、
-KSG-32またはKSG-42またはKSG-320またはKSG-30(活性材料中25%、INCI名:ラウリルPEG-15ジメチコンビニルジメチコンクロスポリマー)、
-KSG-33(活性材料中20%)、
-KSG-210(活性材料中25%、INCI名:ジメチコン/PEG-10/15クロスポリマー)、
-KSG-310:ポリオキシエチレン化ラウリル修飾ポリジメチルシロキサン含有鉱油、
-KSG-330、
-KSG-340、
-X-226146(活性材料中32%、INCI名:ジメチコン/PEG-10ジメチコンビニルジメチコンクロスポリマー)、または
Dow Corning社より、以下の商品名で販売されている製品:
-DC9010(活性材料中9%、INCI名:PEG-12ジメチコンクロスポリマー)
-DC9011(活性材料中11%)
が言及し得る。
-KSG-710(活性材料中25%、INCI名:ジメチコン/ポリグリセリン-3クロスポリマー、
-KSG-810、
-KSG-820、
-KSG-830、
-KSG-840
が言及され得る。
R1およびR3が、C8〜C16直鎖アルキル基を表し、
R2が、C2〜C8アルキレン基を表し、
XおよびYが、(C2H4O)x-RF{ここで、x=10〜15、RF=-SO3M基、Mはアルカリ原子を表す}]
によって特徴づけられるアニオン性界面活性剤である。
-Ceralution(登録商標)H:ベヘニルアルコールと、グリセリルステアラートと、グリセリルステアラートシトラートと、ナトリウムジココイルエチレンジアミンPEG-15サルファート、
-Ceralution(登録商標)F:ラウロイル乳酸ナトリウムと、ナトリウムジココイルエチレンジアミンPEG-15サルファート、
-Ceralution(登録商標)C:水と、カプリン/カプリルトリグリセリドと、グリセリンと、Ceteareth-25と、ナトリウムジココイルエチレンジアミンPEG-15サルファートと、ラウロイル乳酸ナトリウムと、ベヘニルアルコールと、グリセリルステアラートと、グリセリルステアラートシトラートと、アラビアガムと、キサンタンガムと、フェノキシエタノールと、メチルパラベンと、エチルパラベンと、ブチルパラベンと、イソブチルパラベン(INCI名)。
ジメチコンおよびジメチコン/ビニルジメチコンクロスポリマー(市販品としては、SHIN ETSU社より販売されている<<KSG6>>、<<KSG16>>)、
-シクロペンタシロキサンおよびジメチコン/ビニルジメチコンクロスポリマー(市販品としては、SHIN ETSU社より販売されている「KSG-15」、「KSG24」、またDOW CORNING社より販売されている<<Dow Corning 9040 Silicone Elastomer Blend>>)、
-ジメチコンおよびジメチコンクロスポリマー(市販品としては、DOW CORNING社より販売されている<<Dow Corning 9041 Silicone Elastomer Blend>>)、
-鉱油およびビニルジメチコン/ラウリルジメチコンクロスポリマー(SHIN ETSU社より販売されている「KSG41」)、
-イソドデカンおよびビニルジメチコン/ラウリルジメチコンクロスポリマー(SHIN ETSU社より販売されている「KSG42」)、
-トリエチルヘキサノインおよびビニルジメチコン/ラウリルジメチコンクロスポリマー(SHIN ETSU社より販売されている<<KSG43>>)、
-スクアランおよびビニルジメチコン/ラウリルジメチコンクロスポリマー(SHIN ETSU社より販売されている「KSG44」)。
-セルフタンニング剤、即ち、皮膚、特に顔に適用したときに、太陽に対する(自然な日焼け)またはUVランプ下の長期曝露から生じ得る外観に多少なりと類似する黄褐色を生じ得る物質、
-付加的着色剤、即ち、皮膚に特に親和性があり、持続的で非被覆性の着色(即ち、皮膚を不透明にする傾向がない着色)を皮膚に与え、水または溶媒で除去されず、界面活性剤を含有する溶液で擦るおよび洗うことの両方に耐える任意の化合物、である。よって、そのような持続的な着色は、例えばメーキャップ顔料およびその混合物によって提供される表面的および一過性の着色とは識別される。
(i)メラニン形成の生物学的経路を妨害してその効果を高める化合物、例えば、チロシナーゼ基質、MC1Rアゴニスト、
(ii)モノカルボニル化合物またはポリカルボニル合成物(例えばイサチン、アロキサン、ニンヒドリン、グリセルアルデヒド、メソ酒石酸アルデヒド(mesotartaric aldehyde)、グルタルアルデヒド、エリトルロース、特許出願FR2466492およびWO97/35842に記載されているピラゾリン-4,5-ジオン誘導体、ジヒドロキシアセトン(DHA)、ならびに特許出願EP903342に記載されている4,4-ジヒドロキシピラゾリン-5-オン誘導体。好ましくは、DHAが使用される。
-テトラブロモフルオレセイン、またはCTFA名:CI45380で知られるエオシン、またはレッド21、
-CTFA名:CI45410で知られるフロキシンB、またはレッド27、
-CTFA名:CI45425で知られるジヨードフルオレセイン、またはオレンジ10、
-CTFA名:CI45370で知られるジブロモフルオレセイン、またはオレンジ5、
-CTFA名:CI45380(Na塩)で知られるテトラブロモフルオレセインのナトリウム塩、またはレッド22、
-CTFA名:CI45410(Na塩)で知られるフロキシンBのナトリウム塩、またはレッド28、
-CTFA名:CI45425(Na塩)で知られるジヨードフルオレセインのナトリウム塩、またはオレンジ11、
-CTFA名:CI45430で知られるエリスロシン、またはアシッドレッド51、
-CTFA名:CI45405で知られるフロキシン、またはアシッドレッド98。
A.メロシアニンUV吸収剤の調製例
融点:139.4〜141.0℃。
融点:101℃。
融点:130℃。
融点:144.5〜146.0℃。
融点:81.5℃。
融点:78.0℃。
融点:92.7℃。
融点:84.7〜85.3℃。
融点:73℃。
HPLC(210nm):99.3A-%。
メロシアニン誘導体のUV遮蔽特性を、エタノール中のUVスペクトルを測定することによって調べる。以下の表に、調べた最大吸収(λmax)と、対応するA1% 1cm値とを、共に列挙する。
水性相ならびに油相AおよびBを、原材料を80℃で撹拌しながら混合することによって調製する;得られた溶液は、肉眼的に均一である。エマルジョンは、15分の間に4000RPMの回転速度でロータ/ステータMoritzホモジナイザーを使用してせん断しながら、水性相中に油相B1をゆっくり導入することで調製する。次いで、エマルジョン温度を、撹拌下、80℃から40℃に低下させる。次いで、油相B2を、低せん断下、エマルジョンに導入する。エマルジョンを、低せん断下、室温に冷却する。エマルジョンは、1〜10μmの間の大きさの液滴によって特徴付けられる。
持続型即時黒化(Persistant Pigmentation Darkening)(PPD)を、紫外線防護指数(Sun Protection Factor)(SPF)に関するB. L. Diffeyの論文J. Soc. Cosmet. Chem. 40、127〜133、(1989)に記載のin vitro法を使用して測定する。測定は、Labsphere UV-1000S分光光度計を使用して実施する。処方物を、粗いPPMA板上に塗布し、1mg/cm2の割合の均一なフィルムを得る。
厚さ約20μmのフィルムに延ばした処方物を、太陽光シミュレータに曝露することで生じた各UVフィルター(メロシアニン化合物とジベンゾイルメタン化合物)の残量百分率を測定した。
太陽光シミュレータ: 4つのポーチ出口、81017フィルター、および二色性ミラーを備える、装置Oriel 1000W。試料を、水平位置で曝露した。
-UVBフラックス0.35〜0.45mW/cm2
-UVAフラックス16〜18mW/cm2。
約20mgの組成物を、粗い溶融シリカディスクの表面に延ばす。
化合物の化学安定性は、0.5%で化合物を溶解させた水/エタノール(1/1)溶液で評価し得る。
ダイオードアレイ(diod array)検出器eλ(Waters)を備えたUPLC Acquity(Waters)。
カラム:Acquity HSS T3(Waters)、長さ:50mm、内径:2.1mm、粒子径:1.8μm。移動相A=酢酸アンモニウム 20mM、B=アセトニトリル。
直線勾配t(分)
%A %B
0 95 05
5 05 95
8 05 95
8.5 95 05
10 95 05
流量:0.5mL/分
T:20℃
UV383nmで検出
分析:lμL注入
化合物25の溶出時間:2.56分
化合物15の溶出時間:2.11分
酸媒体安定性
Claims (11)
- UVA照射およびUVB照射の両方を遮蔽するシステムをさらに含有する、請求項1に記載の組成物。
- UVAおよび/またはUVBに活性である1つまたは複数の補足的な親水性、親油性もしくは不溶性の有機遮蔽剤および/または1つまたは複数の無機遮蔽剤をさらに含有する、請求項1または2に記載の組成物。
- 少なくとも1つのジベンゾイルメタン誘導体をさらに含有する、請求項1から3のいずれか一項に記載の組成物。
- 油およびワックスから選択される少なくとも1つの脂肪物質を含む、請求項1から4のいずれか一項に記載の組成物。
- 少なくとも1つの親水性または親油性増粘剤を含む、請求項1から5のいずれか一項に記載の組成物。
- イヌリンラウリルカルバメートとしての疎水性改変イヌリンタイプの少なくとも1つの乳化剤を含む、請求項1から6のいずれか一項に記載の組成物。
- 少なくとも1つの脱色素剤を含む、請求項1から7のいずれか一項に記載の組成物。
- 請求項1から8のいずれか一項に記載の化粧品組成物を皮膚に適用するステップを含む、UV照射曝露下の皮膚の黒色化および肌色の均一性を制御および/または改善するための化粧方法。
- 請求項1から8のいずれか一項に記載の化粧品組成物をケラチン物質に適用するステップを含む、ケラチン物質を光老化に対して防護するための化粧方法。
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PCT/EP2012/064195 WO2013011094A2 (en) | 2011-07-21 | 2012-07-19 | Cosmetic and/or dermatological composition containing a merocyanine derivative comprising specific polar groups consisting of hydroxyl- and ether-functionalities |
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WO (2) | WO2013010590A1 (ja) |
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WO2013010590A1 (en) | 2011-07-21 | 2013-01-24 | L'oreal | Cosmetic and/or dermatological composition containing a merocyanine derivative comprising specific polar groups consisting of hydroxyl- and ether-functionalities |
FR3001134B1 (fr) * | 2013-01-21 | 2015-06-19 | Oreal | Composition cosmetique ou dermatologique comprenant une merocyanine et un compose bis-resorcinyl triazine |
FR3001142B1 (fr) * | 2013-01-21 | 2015-06-19 | Oreal | Composition cosmetique ou dermatologique comprenant un filtre uva organique hydrophile et au moins une merocyanine |
FR3001131B1 (fr) | 2013-01-21 | 2015-06-19 | Oreal | Emulsion cosmetique ou dermatologique comprenant une merocyanine et un systeme emulsionnant contenant un tensioactif gemine. |
FR3001133B1 (fr) | 2013-01-21 | 2015-03-20 | Oreal | Composition cosmetique ou dermatologique comprenant une merocyanine et une phase huileuse comprenant au moins un compose amide particulier |
FR3001216B1 (fr) | 2013-01-21 | 2015-02-27 | Oreal | Composition cosmetique ou dermatologique comprenant une merocyanine, une phase huileuse et un mono-alcanol en c1-c4 |
FR3001128B1 (fr) | 2013-01-21 | 2015-06-19 | Oreal | Emulsion cosmetique ou dermatologique comprenant une merocyanine et un systeme emulsionnant contenant un sel de metal alcalin d'ester d'acide phosphorique et d'alcool gras |
FR3001141B1 (fr) * | 2013-01-21 | 2015-06-19 | Oreal | Composition cosmetique ou dermatologique comprenant une merocyanine, un filtre triazine uvb et un filtre uva organique additionnel |
FR3001140B1 (fr) * | 2013-01-21 | 2015-06-19 | Oreal | Composition cosmetique ou dermatologique comprenant une merocyanine, un filtre uvb organique hydrophile et un filtre uva organique additionnel |
FR3001136B1 (fr) | 2013-01-21 | 2015-06-19 | Oreal | Emulsion cosmetique ou dermatologique comprenant une merocyanine et un systeme emulsionnant contenant un polymere amphiphile comportant au moins un motif acide acrylamido 2-methylpropane sulfonique |
ES2727132T3 (es) * | 2013-01-21 | 2019-10-14 | Oreal | Composición cosmética o dermatológica que comprende una merocianina y un agente de filtración de UVA del tipo de 2-hidroxibenzofenona aminosustituida y/o un agente de filtración de UVA orgánico hidrófilo |
FR3001139B1 (fr) * | 2013-01-21 | 2015-06-19 | Oreal | Composition cosmetique ou dermatologique comprenant une merocyanine, un filtre uvb organique lipophile liquide et un filtre uva organique additionnel |
WO2014111574A1 (en) | 2013-01-21 | 2014-07-24 | L'oreal | Cosmetic or dermatological composition comprising a merocyanine, an organic uvb-screening agent and an additional organic uva-screening agent |
WO2014111566A2 (en) | 2013-01-21 | 2014-07-24 | L'oreal | Cosmetic or dermatological composition comprising a merocyanine and an insoluble organic uv-screening agent and/or an insoluble inorganic uv- screening agent |
EP2945601B1 (en) | 2013-01-21 | 2018-08-22 | L'Oréal | Cosmetic or dermatological composition comprising a merocyanine and a lipophilic benzotriazole uv-screening agent and/or a bis-resorcinyl triazine compound |
FR3001137B1 (fr) * | 2013-01-21 | 2015-02-27 | Oreal | Emulsion eau-dans-huile cosmetique ou dermatologique comprenant une merocyanine et au moins un polymere emulsionnant du type ester d'acide gras et de glycol polyoxyalkylene |
FR3001135B1 (fr) * | 2013-01-21 | 2015-06-19 | Oreal | Composition cosmetique ou dermatologique comprenant une merocyanine et un filtre uv inorganique insoluble |
FR3001132B1 (fr) * | 2013-01-21 | 2015-05-29 | Oreal | Composition cosmetique ou dermatologique comprenant une merocyanine et un compose 2-hydroxybenzophenone aminosubstitue |
FR3001130B1 (fr) * | 2013-01-21 | 2015-06-19 | Oreal | Composition cosmetique ou dermatologique comprenant une merocyanine et un filtre uv organique insoluble |
FR3001129B1 (fr) * | 2013-01-21 | 2015-06-19 | Oreal | Composition cosmetique ou dermatologique comprenant une merocyanine et un filtre uv benzotriazole lipophile |
FR3001138B1 (fr) * | 2013-01-21 | 2015-06-19 | Oreal | Composition anhydre cosmetique ou dermatologique comprenant une merocyanine et une phase huileuse |
US8932573B2 (en) | 2013-03-22 | 2015-01-13 | L'oreal | Mascara compositions comprising a semicrystalline polymer, a silicone elastomer, and a hydrophilic gelling agent |
US9192562B2 (en) | 2013-09-18 | 2015-11-24 | L'oreal | High color intensity and easily removable mascara |
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FR3046928B1 (fr) | 2016-01-26 | 2019-08-09 | L'oreal | Composition cosmetique ou dermatologique comprenant une merocyanine et une phase huileuse comprenant au moins un amide n-substitue |
FR3046929B1 (fr) * | 2016-01-26 | 2018-03-02 | L'oreal | Composition cosmetique ou dermatologique comprenant une merocyanine et une phase huileuse comprenant au moins un ester d'acide di ou tricarboxylique |
FR3046927B1 (fr) * | 2016-01-26 | 2018-03-02 | L'oreal | Composition cosmetique ou dermatologique comprenant une merocyanine et une phase huileuse comprenant au moins un ether d'isosorbide |
FR3046930B1 (fr) * | 2016-01-26 | 2018-03-02 | L'oreal | Composition cosmetique ou dermatologique comprenant une merocyanine et une phase huileuse comprenant au moins un polyalkyleneglycol |
FR3048359B1 (fr) * | 2016-03-01 | 2020-11-06 | Oreal | Utilisation d’au moins un filtre uva long pour prevenir l’apparition de sensations dysesthesiques |
FR3060361B1 (fr) | 2016-12-21 | 2018-12-07 | L'oreal | Emulsion eau-dans-huile comprenant un systeme emulsionnant particulier, une argile lipophile, une poudre d’organopolysiloxane elastomerique enrobee d’une resine de silicone |
FR3060355B1 (fr) | 2016-12-21 | 2020-01-24 | L'oreal | Emulsion eau-dans-huile contenant la baicaline, une base xanthique, une vitamine b3 et un sel de cation metallique multivalent |
FR3060997B1 (fr) | 2016-12-23 | 2019-05-31 | L'oreal | Composition comprenant de la baicaline |
FR3068354B1 (fr) * | 2017-06-29 | 2020-07-31 | Oreal | Compositions photoprotectrices comprenant un derive dibenzoylmethane, un compose merocyanine et un compose susceptible d'accepter l'energie de niveau excite triplet du compose dibenzoylmethane |
FR3073402B1 (fr) | 2017-11-15 | 2020-05-15 | L'oreal | Composition comprenant de la baicaline et/ou l’un de ses derives et un polymere acrylique particulier |
FR3073400A1 (fr) | 2017-11-15 | 2019-05-17 | L'oreal | Emulsion cosmetique contenant un tensioactif gemine et un polymere lipophile |
US10426424B2 (en) | 2017-11-21 | 2019-10-01 | General Electric Company | System and method for generating and performing imaging protocol simulations |
PL423966A1 (pl) * | 2017-12-20 | 2019-07-01 | Marek Łukowski | Komora krioterapeutyczna dla zwierząt, w szczególności dla koni |
FR3083097B1 (fr) * | 2018-06-28 | 2020-11-27 | Oreal | Composition cosmetique ou dermatologique comprenant une merocyanine et une phase huileuse comprenant au moins un carbonate d’alkyle ou d’alkylene |
WO2020011766A1 (en) * | 2018-07-12 | 2020-01-16 | Basf Se | Merocyanine crystallization process |
CN111087451B (zh) * | 2020-03-19 | 2020-07-17 | 广州市新纪元化妆品有限公司 | 一种能够增加皮肤抗皱功能的化合物及其在制备化妆品中的用途 |
FR3117824A1 (fr) | 2020-12-18 | 2022-06-24 | L'oreal | Composition cosmétique ou dermatologique comprenant une mérocyanine et une phase huileuse comprenant au moins un ester d’acide citrique |
FR3117825A1 (fr) * | 2020-12-18 | 2022-06-24 | L'oreal | Composition cosmétique ou dermatologique comprenant une mérocyanine, un filtre UV triazine, et un polysaccharide modifié par des chaînes hydrophobes |
FR3130596A1 (fr) * | 2021-12-17 | 2023-06-23 | L'oreal | Composition cosmétique et/ou dermatologique comprenant au moins une mérocyanine et au moins de l’acide ascorbique et/ou l’un de ses dérivés |
FR3130594A1 (fr) | 2021-12-17 | 2023-06-23 | L'oreal | Composition cosmétique ou dermatologique comprenant une mérocyanine et du resvératrol et/ou un dérivé de resvératrol |
FR3130597A1 (fr) | 2021-12-17 | 2023-06-23 | L'oreal | Composition cosmétique ou dermatologique comprenant une mérocyanine et au moins un diol comportant de 4 à 7 atomes de carbone |
FR3130595A1 (fr) * | 2021-12-17 | 2023-06-23 | L'oreal | Composition cosmétique ou dermatologique comprenant au moins une mérocyanine et un hydrotrope |
FR3130593A1 (fr) | 2021-12-17 | 2023-06-23 | L'oreal | Composition cosmétique ou dermatologique comprenant une mérocyanine et le dipropylène glycol |
FR3130598A1 (fr) | 2021-12-17 | 2023-06-23 | L'oreal | Composition cosmétique ou dermatologique comprenant une mérocyanine et du tétra hydroxycinnamate de di-t-butyle pentaérythrityle |
FR3141059A1 (fr) * | 2022-10-20 | 2024-04-26 | L'oreal | Composition cosmétique ou dermatologique comprenant une mérocyanine et une gamma-butyrolactone et/ou un gamma-butyrolactame |
WO2023110767A1 (en) * | 2021-12-17 | 2023-06-22 | L'oreal | Cosmetic or dermatological composition comprising a merocyanine and a gamma-butyrolactone and/or a gamma-butyrolactam |
FR3130599A1 (fr) * | 2021-12-17 | 2023-06-23 | L'oreal | Composition cosmétique ou dermatologique comprenant une mérocyanine et une gamma-butyrolactone et/ou un gamma-butyrolactame |
FR3132637A1 (fr) | 2022-02-15 | 2023-08-18 | L'oreal | Composition cosmétique ou dermatologique comprenant une mérocyanine et un complexe polyionique |
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BR112014001331B1 (pt) | 2018-12-04 |
AU2012285709B2 (en) | 2017-03-02 |
AU2012285709A8 (en) | 2014-01-30 |
EP2734180A2 (en) | 2014-05-28 |
PT2734180T (pt) | 2021-06-21 |
US20140294743A1 (en) | 2014-10-02 |
ES2875020T3 (es) | 2021-11-08 |
US11458083B2 (en) | 2022-10-04 |
JP2014529337A (ja) | 2014-11-06 |
WO2013011094A4 (en) | 2013-07-11 |
KR20140054102A (ko) | 2014-05-08 |
CN103917218B (zh) | 2017-06-09 |
RU2609859C2 (ru) | 2017-02-06 |
DK2734180T3 (da) | 2021-06-21 |
KR102052772B1 (ko) | 2019-12-05 |
CN107260561A (zh) | 2017-10-20 |
CN103917218A (zh) | 2014-07-09 |
CN107260561B (zh) | 2022-05-17 |
BR112014001331A2 (pt) | 2017-06-27 |
WO2013011094A2 (en) | 2013-01-24 |
WO2013010590A1 (en) | 2013-01-24 |
AU2012285709A1 (en) | 2014-01-09 |
WO2013011094A3 (en) | 2013-06-06 |
RU2014106433A (ru) | 2015-08-27 |
EP2734180B1 (en) | 2021-03-31 |
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