JP5559152B2 - 化粧用組成物または医薬組成物を調製するための、有機変性シロキサンブロックコポリマーの使用 - Google Patents
化粧用組成物または医薬組成物を調製するための、有機変性シロキサンブロックコポリマーの使用 Download PDFInfo
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- JP5559152B2 JP5559152B2 JP2011508858A JP2011508858A JP5559152B2 JP 5559152 B2 JP5559152 B2 JP 5559152B2 JP 2011508858 A JP2011508858 A JP 2011508858A JP 2011508858 A JP2011508858 A JP 2011508858A JP 5559152 B2 JP5559152 B2 JP 5559152B2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
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- C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/373—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicones
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
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- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
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- A61Q1/02—Preparations containing skin colorants, e.g. pigments
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- 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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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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Description
A)一般式I
R1は、同一かまたは異なる、分岐または非分岐の、1〜20個の炭素原子を有する脂肪族炭化水素基または芳香族炭化水素基であり、
R2は、R1またはHであり、但し少なくとも3つの基R2はHであり、
aは、5〜500、好ましくは10〜250、特に15〜75であり、
bは、1〜50、好ましくは1〜20、特に3〜15であり、
cは、0〜5、好ましくは0〜1、特に0である)
の有機ポリシロキサンの、
二重結合を含む一般式II
dは、10〜1000、好ましくは101〜750、特に201〜500であり、かつ
R3は、互いに独立に、2〜12個、好ましくは2〜8個、特に2個の炭素原子を有し、かつ少なくとも1つの二重結合を含む、同一かまたは異なる炭化水素基である)
のシロキサンへの、白金触媒またはロジウム触媒の存在下での付加反応
(但し、一般式Iの有機ポリシロキサンは、二重結合を含む一般式IIのシロキサンを基準にして少なくとも6倍モル過剰で存在し、これによりSi−H基を有する反応生成物が得られ、かつ反応段階の少なくとも1つでその反応生成物がさらに反応する)、
B)遷移金属触媒による、アルケニル化合物および/またはアルキニル化合物への、好ましくは二重結合含有ポリエーテルおよびα−オレフィンへの、特にアリルポリエーテルへの、SiH基の部分的または完全付加
あるいは
C)触媒の存在下、直鎖または分岐の、飽和、一価不飽和または多価不飽和の、芳香族、脂肪族―芳香族、場合によりハロゲン原子含有の、モノアルコール、ポリエーテルモノアルコール、ポリエステルモノアルコール、アミノアルコールの群からの少なくとも1つのアルコールと、上述の反応後に残っているSi−H基の、部分的反応または完全反応
によって調製されている有機変性シロキサンブロックコポリマーを含む乳化剤システムを提供する。
で示される理想化された「H構造」のシロキサンを形成する。
皮膚軟化剤、
乳化剤および界面活性剤、
増粘剤/粘度調節剤/安定剤、
UV光防御用フィルター、
酸化防止剤、
ヒドロトロープ(またはポリオール)、
固体およびフィラー、
膜形成剤、
真珠光沢添加物、
消臭および制汗有効成分、
防虫剤、
セルフタンニング剤、
保存料、
コンディショナー、
香料、
染料、
化粧用有効成分、
ケア用添加物、
過脂肪剤、
溶剤、
の群から選択される少なくとも1つの追加的成分を含むことができる。
8〜22個の炭素原子を有する直鎖脂肪アルコールへの、12〜22個の炭素原子を有する脂肪酸への、およびアルキル基中に8〜15個の炭素原子を有するアルキルフェノールへの、エチレンオキシド2〜100モルおよび/またはプロピレンオキシド0〜5モルの、付加生成物、
エチレンオキシド1〜100モルの、グリセロールへの付加生成物の、C12/18−脂肪酸モノエステルおよびジエステル、
6〜22個の炭素原子を有する飽和および不飽和脂肪酸の、グリセロールモノエステルおよびジエステル、ならびにソルビタンモノエステルおよびジエステル、およびそれらのエチレンオキシド付加生成物、
8〜22個の炭素原子をアルキル基中に有するアルキルモノグリコシドおよびアルキルオリゴグリコシドならびにそれらのエチレンオキシド付加生成物、
エチレンオキシド2〜200モルの、ヒマシ油および/または水素化ヒマシ油への、付加生成物、
直鎖、分岐した、不飽和または飽和の、C6〜C22−脂肪酸、リシノール酸、および12−ヒドロキシステアリン酸およびグリセロール、ポリグリセロール、ペンタエリトリトール、ジペンタエリスリトール、糖アルコール(たとえばソルビトール)、アルキルグルコシド(たとえばメチルグルコシド、ブチルグルコシド、ラウリルグルコシド)およびポリグルコシド(たとえばセルロース)を基本とする、部分エステル、
モノ−、ジ−およびトリアルキルリン酸、ならびにモノ−、ジ−および/またはトリ−PEGアルキルリン酸およびそれらの塩、
ポリシロキサン−ポリエーテルコポリマー(ジメチコンコポリオール)、たとえばPEG/PPG−20/6ジメチコン、PEG/PPG−20/20ジメチコン、ビス−PEG/PPG−20/20ジメチコン、PEG−12ジメチコン、PEG−14ジメチコン、PEG/PPG−14/4、PEG/PPG−4/12、PEG/PPG−20/20、PEG/PPG−18/18、PEG/PPG−17/18またはPEG/PPG−15/15等、
ポリシロキサン−ポリアルキル−ポリエーテルコポリマーおよび対応する誘導体、たとえば、ラウリルジメチコンコポリオールまたはセチルジメチコンコポリオール等、特にセチルPEG/PPG−10/1ジメチコン(ABIL(登録商標)EM90(Evonik))、
ドイツ特許第1165574号に記載のペンタエリトリトール、脂肪酸、クエン酸および脂肪アルコールの混合エステルおよび/または6〜22個の炭素原子を有する脂肪酸、メチルグルコースおよびポリオール、たとえば、グリセロールまたはポリグリセロール等の、混合エステル、
クエン酸エステル、たとえば、クエン酸ステアリン酸グリセリル、クエン酸オレイン酸グリセリルおよびクエン酸ジラウリル等。
3―ベンジリデンカンファーおよびその誘導体、たとえば3―(4―メチルベンジリデン)カンファー、
4−アミノ安息香酸誘導体、たとえば、4−(ジメチルアミノ)安息香酸2−エチルヘキシルおよび4−(ジメチルアミノ)安息香酸アミル等、
桂皮酸のエステル、たとえば4−メトキシ桂皮酸2−エチルヘキシル、4−メトキシ桂皮酸イソペンチル、2−シアノ−3−フェニル桂皮酸2−エチルヘキシル(オクトクリレン)等、
サリチル酸のエステル、たとえば、2−サリチル酸エチルヘキシル、サリチル酸4−イソプロピルベンジル、サリチル酸ホモメンチル等、
ベンゾフェノンの誘導体、たとえば、2−ヒドロキシ−4−メトキシベンゾフェノン、2−ヒドロキシ−4−メトキシ−4’―メチルベンゾフェノン、2,2’−ジヒドロキシ−4−メトキシベンゾフェノン等、
ベンザルマロン酸のエステル、たとえば、4−メトキシベンザルマロン酸ジ−2−エチルヘキシル等、
トリアジン誘導体、たとえば、2,4,6−トリアニリノ−(p−カルボ−2’−エチル−1’−ヘキシルオキシ)−1,3,5−トリアジンおよびオクチルトリアゾン等、
プロパン-1,3-ジオン、たとえば、1ー(4-tert-ブチルフェニル)−3−(4’−メトキシフェニル)プロパン−1,3−ジオン等、
である。
2−フェニルベンズイミダゾール−5−スルホン酸およびそのアルカリ金属塩、アルカリ土類金属塩、アンモニウム塩、アルキルアンモニウム塩、アルカノールアンモニウム塩およびグルカンモニウム塩、
ベンゾフェノンのスルホン酸誘導体、たとえば、2−ヒドロキシ−4−メトキシベンゾフェノン−5−スルホン酸およびその塩等、
3−ベンジリデンカンファーのスルホン酸誘導体、たとえば、4−(2−オキソ−3−ボルニリデンメチル)ベンゼンスルホン酸および2−メチル−5−(2−オキソ−3−ボルニリデン)スルホン酸ならびにそれらの塩等、
である。
グリセロールアルキレングリコール、たとえば、エチレングリコール、ジエチレングリコール、プロピレングリコール、ブチレングリコール、ヘキシレングリコール、および平均分子量が100〜1000ダルトンのポリエチレングリコール等、自己縮合度が1.5〜10のテクニカルグレードオリゴグリセロール混合物、たとえば、ジグリセロール含量が40〜50重量%のテクニカルグレードジグリセロール混合物等、メチロール化合物、特にトリメチロールエタン、トリメチロールプロパン、トリメチロールブタン、ペンタエリトリトールおよびジペンタエリスリトール等、低級アルキルグルコシド、特に1〜4個の炭素原子がアルキル基中にあるもの、たとえば、メチルグルコシドおよびブチルグルコシド等、5〜12個の炭素原子を有する糖アルコール、たとえば、ソルビトールまたはマンニトール、5〜12個の炭素原子を有する糖、たとえば、グルコースまたはスクロース等、アミノ糖、たとえば、グルカミン等、
である。
乳化剤実施例:
乳化剤1(本発明による)(O/W乳化剤):
調製:先ず第一に、一般式Me3SiO(SiMe2O)28(SiMeHO)10SiMe3のSi−H官能性シロキサン183gを、一般式CH2=CH−SiMe2O−(SiMe2O)348−SiMe2−CH=CH2のビニルシロキサン143gと混合し、120℃に加熱して、1ppmのRh触媒を加えた。30分後、次には一般式CH2=CH−CH2−O−(CH2CH2O)25(CH2CH(CH3)O)4Meのアリルポリエーテル1322gを加え、その混合物を94℃まで冷却し、8ppmの白金触媒を加えた。次いで、その混合物をさらに、120℃で2時間撹拌した。
調製:まず第一に、一般式Me3SiO(SiMe2O)38−(SiMeHO)9SiMe3のSi−H官能性シロキサン42gを、一般式CH2=CH−SiMe2O−(SiMe2O)280−SiMe2−CH=CH2のビニルシロキサン21gと混合し、120℃に加熱し、さらに1ppmのRh触媒を加えた。30分後、次には一般式CH2=CH−CH2−O−(CH2CH2O)25(CH2CH(CH3)O)4Meのアリルポリエーテル148gを加え、その混合物を90℃まで冷却し、10ppmのPt触媒を加えた。次いで、その混合物をさらに、120℃で2時間撹拌し、生成物を濾過した。
調製:先ず第一に、一般式Me3SiO(SiMe2O)73−(SiMeHO)25SiMe3のSi−H官能性シロキサン144gを、一般式CH2=CH−SiMe2O−(SiMe2O)348−SiMe2−CH=CH2のビニルシロキサン26gと混合し、90℃に加熱して、5ppmのRh触媒を加えた。次に、一般式CH2=CH−CH2−O―(CH2CH2O)8OHのアリルポリエーテル32gおよび1−ヘキサデセン117gを加えた。この間に、温度は113℃に上昇した。次いで、この混合物をさらに、110℃で2時間撹拌し、真空で生成物から揮発性成分を除去した。
比較用乳化剤1〜5の構造は、一般式:
R1(CH3)2SiO−[(CH3)2SiO]n−[(CH3)R2SiO]m−Si(CH3)2R1
(式中:R1,R2=CH3または−(CH2)w−O−(C2H4O)x−(C3H6O)y−R3(式中R3=HまたはCH3)型のポリエーテル(「PE」)
に対応する。
先ず第一に、一般式Me3SiO(SiMe2O)28(SiMeHO)10SiMe3のSi−H官能性シロキサン240gを、一般式CH2=CH−SiMe2O−SiMe2−CH=CH2のビニルシロキサン1.3gと混合し、120℃に加熱し、その混合物に1ppmのRh触媒を加えた。30分後、次には一般式CH2=CH−CH2−O−(CH2CH2O)25(CH2CH(CH3)O)4Meのアリルポリエーテル1732gを加え、その混合物を94℃まで冷却し、8ppmの白金触媒を加えた。次いでその混合物をさらに、120℃で2時間撹拌した。
適用例に示されている濃度は全て、重量%による。乳化物を調製するために、当業者に周知の通例の均質化方法を使用した。
O/W乳化物における乳化力を調査するために、まさしく臨界条件下で(僅か0.5%の乳化剤)、どの構造が優れた乳化活性で際立っているかを非常に迅速に示す、迅速試験を使用した。
相Aおよび相Bを室温で混合し、撹拌せずにCを加える。次いで、この混合物を1分間均質化する。相Dおよび相Eを加え、次いで、再度1分間均質化する。
本発明による2つの乳化剤実施例1および実施例2の皮膚感触および安定性を調査するために、化粧用製剤(乳化物実施例3および4)中に2%濃度でこれらを使用した。
これらの例は、本発明による乳化剤を、多数の化粧用製剤で使用できることを示すためである。本発明による乳化剤の親水性に応じて、O/W乳化物またはW/O乳化物を調製することが可能である。さらに、本発明による乳化剤の助けを借りて、顔料または固体を、乳化物調製物に安定に組み入れることが可能である。さらに、実施例は、代表的な共乳化剤、油、増粘剤、および安定剤と、良好な相溶性を示す。
Claims (16)
- A)一般式I
(式中、
R1は、同一かまたは異なる、1〜20個の炭素原子を有する、脂肪族炭化水素基または芳香族炭化水素基であり、
R2は、R1またはHであり、但し少なくとも3つの基R2はHであり、
aは、5〜500であり、
bは、1〜50であり、
cは、0〜5である)
で表される有機ポリシロキサンの、
二重結合を含む一般式II
(式中、
dは、10〜1000であり、かつ、R3は、互いに独立に、2〜12個の炭素原子を有し、かつ少なくとも1つの二重結合を含む、同一かまたは異なる炭化水素基である)
で表されるシロキサンへの、白金触媒またはロジウム触媒の存在下での付加反応と
(但し、一般式Iの有機ポリシロキサンは、二重結合を含む一般式IIのシロキサンを基準にして少なくとも6倍モル過剰で存在し、これによりSi−H基を有する反応生成物が得られる)、
前記A)の反応生成物の、次のステップの少なくとも1つにおける反応:
B)遷移金属触媒による、アルケニル化合物および/またはアルキニル化合物への、SiH基の部分的または完全付加反応;
および
C)触媒の存在下、直鎖または分岐の、飽和、一価不飽和または多価不飽和の、芳香族、脂肪族−芳香族、場合によりハロゲン原子含有の、モノアルコール、ポリエーテルモノアルコール、ポリエステルモノアルコール、アミノアルコールの群からの少なくとも1つのアルコールと、上述の反応後に残っているSi−H基の、部分的反応または完全反応;
によって調製される有機変性シロキサンブロックコポリマーを含む乳化剤組成物の、化粧用製剤、皮膚外用製剤または医薬製剤中における、油中水型乳化剤、水中油型乳化剤またはシリコーン中水型乳化剤としての、あるいは分散助剤としての使用。 - R1が、同一かまたは異なる、非分岐の、1〜9個の炭素原子を有する、脂肪族炭化水素基または芳香族炭化水素基であることを特徴とする、請求項1に記載の使用。
- ステップB)において、前記付加が、アリルポリエーテルへの付加であることを特徴とする、請求項1または2に記載の使用。
- ステップB)において、前記付加が、CH 2 =CH−CH 2 −O−(CH 2 CH 2 O) 25 (CH 2 CH(CH 3 )O) 4 MeおよびCH 2 =CH−CH 2 −O―(CH 2 CH 2 O) 8 OHから選択されるアリルポリエーテルへの付加であることを特徴とする、請求項1〜3のいずれか1項に記載の使用。
- ステップC)において、ホウ素含有ルイス酸が触媒として使用されることを特徴とする、請求項1〜4のいずれか1項に記載の使用。
- トリス(ペンタフルオロフェニル)ボラン(C5F4)3Bがホウ素含有ルイス酸として使用されることを特徴とする、請求項5に記載の使用。
- ステップC)において、ホウ素含有ルイス酸に加えて相乗的に有効な化合物が使用されることを特徴とする、請求項5または6に記載の使用。
- 第4、第6、第7および第8亜族ならびに第4族主族の元素の塩の群から選択される塩または陽イオンとの錯体が、相乗的に有効な化合物として使用されることを特徴とする、請求項7に記載の使用。
- ステップC)において、少なくとも1つのカルボン酸および少なくとも1つのカルボン酸の塩を含む触媒混合物が触媒として使用されることを特徴とする、請求項1〜8のいずれか1項に記載の使用。
- 水中油型乳化剤または分散助剤としての、請求項1〜9のいずれか1項に記載の使用。
- 前記有機変性シロキサンブロックコポリマーが、A)の反応生成物の、ステップB)における反応またはステップB)およびC)における反応によって調製される、請求項1〜9のいずれか1項に記載の使用。
- 前記乳化剤組成物が、粒子または顔料を追加成分として含む、請求項1〜9のいずれか1項に記載の使用。
- 前記乳化剤組成物が、化粧用有効成分を追加成分として含む、請求項1〜9のいずれか1項に記載の使用。
- A)一般式I
(式中、
R1は、同一かまたは異なる、1〜20個の炭素原子を有する、脂肪族炭化水素基または芳香族炭化水素基であり、
R2は、R1またはHであり、但し少なくとも3つの基R2はHであり、
aは、5〜500であり、
bは、1〜50であり、
cは、0〜5である)
で表される有機ポリシロキサンの、
二重結合を含む一般式II
(式中、
dは、10〜1000であり、かつ、R3は、互いに独立に、2〜12個の炭素原子を有し、かつ少なくとも1つの二重結合を含む、同一かまたは異なる炭化水素基である)
で表されるシロキサンへの、白金触媒またはロジウム触媒の存在下での付加反応と
(但し、一般式Iの有機ポリシロキサンは、二重結合を含む一般式IIのシロキサンを基準にして少なくとも6倍モル過剰で存在し、これによりSi−H基を有する反応生成物が得られる)、
前記A)の反応生成物の、次のステップB)における反応またはステップB)およびC)における反応:
B)遷移金属触媒による、アリルポリエーテルへの、SiH基の部分的または完全付加反応;
C)触媒の存在下、直鎖または分岐の、飽和、一価不飽和または多価不飽和の、芳香族、脂肪族−芳香族、場合によりハロゲン原子含有の、モノアルコール、ポリエーテルモノアルコール、ポリエステルモノアルコール、アミノアルコールの群からの少なくとも1つのアルコールと、上述の反応後に残っているSi−H基の、部分的反応または完全反応;
によって調製される有機変性シロキサンブロックコポリマーを含む、水中油型乳化剤組成物であって、
化粧用製剤、皮膚外用製剤または医薬製剤中における乳化剤または分散助剤用の水中油型乳化剤組成物。 - 粒子または顔料を追加成分として含む、請求項14に記載の乳化剤組成物。
- 化粧用有効成分を追加成分として含む、請求項14に記載の乳化剤組成物。
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DE102005039398A1 (de) * | 2005-08-20 | 2007-02-22 | Goldschmidt Gmbh | Verfahren zur Herstellung von Anlagerungsprodukten aus SiH-Gruppen enthaltenden Verbindungen an Olefingruppen aufweisende Reaktionspartner in wässrigen Medien |
DE102005051939A1 (de) | 2005-10-29 | 2007-05-03 | Goldschmidt Gmbh | Verfahren zur Herstellung von organisch modifizierten Polyorganosiloxanen |
DE102006005100A1 (de) | 2006-02-04 | 2007-08-09 | Goldschmidt Gmbh | Verfahren zur Herstellung organomodifizierter Siloxane |
DE102006035511A1 (de) | 2006-07-31 | 2008-02-07 | Evonik Goldschmidt Gmbh | Neuartige Polysiloxane mit quaternären Ammoniumgruppen, Verfahren zu deren Herstellung und deren Verwendung als Textilweichmacher |
DE102006035512A1 (de) | 2006-07-31 | 2008-02-07 | Evonik Goldschmidt Gmbh | Neuartige Polysiloxane mit quaternären Ammoniumgruppen, Verfahren zu deren Herstellung und deren Verwendung in reinigenden und pflegenden Formulierungen |
DE102006040010A1 (de) * | 2006-08-25 | 2008-02-28 | Evonik Goldschmidt Gmbh | Verwendung von polyethermodifizierten Siloxanblockcopolymeren als hydrophile silikonhaltige Weichmacher für Gewebe, Non-wovens und/oder Fasern aus natürlichen und/oder synthetischen Rohstoffen |
DE102007011251A1 (de) | 2007-03-08 | 2008-09-11 | Evonik Goldschmidt Gmbh | Organisch modifizierte Siloxane und deren Verwendung zur Herstellung von Zubereitungen für wasserabweisende Imprägnierungen |
DE102007041028A1 (de) | 2007-08-29 | 2009-03-05 | Evonik Goldschmidt Gmbh | Verwendung estermodifizierter Organopolysiloxane zur Herstellung kosmetischer oder pharmazeutischer Kompositionen |
DE102008001788A1 (de) | 2008-05-15 | 2009-11-26 | Evonik Goldschmidt Gmbh | Verwendung organomodifizierter Siloxanblockcopolymere zur Herstellung kosmetischer oder pharmazeutischer Zusammensetzungen |
DE102008001786A1 (de) * | 2008-05-15 | 2009-11-26 | Evonik Goldschmidt Gmbh | Verwendung organomodifizierter Siloxanblockcopolymere als Pflegewirkstoff zur Pflege von menschlichen oder tierischen Körperteilen |
DE102008041020A1 (de) | 2008-08-06 | 2010-02-11 | Evonik Goldschmidt Gmbh | Verwendung von Polysiloxanen mit quaternären Ammoniumgruppen zum Schutz von tierischen oder menschlichen Haaren vor Hitzeschädigung |
DE102008041601A1 (de) | 2008-08-27 | 2010-03-04 | Evonik Goldschmidt Gmbh | Verfahren zur Herstellung verzweigter SiH-funtioneller Polysiloxane und deren Verwendung zur Herstellung flüssiger, SiC- oder SiOC-verknüpfter, verzweigter organomodifizierter Polysiloxane |
DE102008042381A1 (de) | 2008-09-26 | 2010-04-01 | Evonik Goldschmidt Gmbh | Emulgator-Systeme für kosmetische und pharmazeutische Öl-in-Wasser-Emulsionen |
-
2008
- 2008-05-15 DE DE102008001788A patent/DE102008001788A1/de not_active Withdrawn
-
2009
- 2009-04-15 CN CN200980117421XA patent/CN102026613B/zh active Active
- 2009-04-15 EP EP09745639.6A patent/EP2273966B1/de active Active
- 2009-04-15 JP JP2011508858A patent/JP5559152B2/ja active Active
- 2009-04-15 BR BRPI0912561A patent/BRPI0912561B1/pt not_active IP Right Cessation
- 2009-04-15 US US12/991,255 patent/US8466248B2/en active Active
- 2009-04-15 WO PCT/EP2009/054426 patent/WO2009138306A1/de active Application Filing
- 2009-04-15 CA CA2724414A patent/CA2724414A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
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JP2011520823A (ja) | 2011-07-21 |
EP2273966B1 (de) | 2018-03-21 |
BRPI0912561A2 (pt) | 2015-10-13 |
CN102026613A (zh) | 2011-04-20 |
DE102008001788A1 (de) | 2009-11-26 |
US8466248B2 (en) | 2013-06-18 |
CA2724414A1 (en) | 2009-11-19 |
WO2009138306A1 (de) | 2009-11-19 |
US20110091399A1 (en) | 2011-04-21 |
EP2273966A1 (de) | 2011-01-19 |
BRPI0912561B1 (pt) | 2016-11-16 |
CN102026613B (zh) | 2013-12-11 |
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