JP5232153B2 - 有機ポリシロキサンを用いて処理された充填剤、色素及び鉱物粉末 - Google Patents
有機ポリシロキサンを用いて処理された充填剤、色素及び鉱物粉末 Download PDFInfo
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- JP5232153B2 JP5232153B2 JP2009528701A JP2009528701A JP5232153B2 JP 5232153 B2 JP5232153 B2 JP 5232153B2 JP 2009528701 A JP2009528701 A JP 2009528701A JP 2009528701 A JP2009528701 A JP 2009528701A JP 5232153 B2 JP5232153 B2 JP 5232153B2
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- polydiorganosiloxane
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- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000010454 slate Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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 description 1
- 239000010902 straw Substances 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 239000010876 untreated wood Substances 0.000 description 1
- 239000002025 wood fiber Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 229940075420 xanthine Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/12—Treatment with organosilicon compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/0081—Composite particulate pigments or fillers, i.e. containing at least two solid phases, except those consisting of coated particles of one compound
- C09C1/0093—Composite particulate pigments or fillers, i.e. containing at least two solid phases, except those consisting of coated particles of one compound whose phases only contain calcium ions, carbonate ions and silicate ions or silica
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/02—Compounds of alkaline earth metals or magnesium
- C09C1/021—Calcium carbonates
- C09C1/022—Treatment with inorganic compounds
- C09C1/024—Coating
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/36—Compounds of titanium
- C09C1/3607—Titanium dioxide
- C09C1/3684—Treatment with organo-silicon compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/40—Compounds of aluminium
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/40—Compounds of aluminium
- C09C1/42—Clays
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/80—Particles consisting of a mixture of two or more inorganic phases
- C01P2004/82—Particles consisting of a mixture of two or more inorganic phases two phases having the same anion, e.g. both oxidic phases
- C01P2004/84—Particles consisting of a mixture of two or more inorganic phases two phases having the same anion, e.g. both oxidic phases one phase coated with the other
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/60—Optical properties, e.g. expressed in CIELAB-values
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- Dispersion Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
DP12.6のヒドロキシ末端ポリジメチルシロキサン288gが、窒素下、数分間、n−プロピルトリメトキシシラン104gと共に攪拌された。チタンn−ブトキシド2gが、攪拌下、次いで、加えられた。その生成物が全て均一となるまでずっと、この混合が継続された。その重合体(ポリマー)生成物A1の特徴化が、GPCにより求められた平均分子量1,700を有し、NMRにより求められたとおりのこの反応時の平均DP15〜19を有する、式中、Rが、プロピルであり、各R’が、メチルである、−SiR(OR’)2の主な基の構造の珪酸n−プロピル官能基ポリジメチルシロキサンの形成を確かめた。分岐単位−SiR(OR’)O0.5 及び分岐単位−SiRO1.0も最終生成物の一部として観察された。或いは、形成されたメタノールが、大気圧において又は減圧下で取り除かれた。
TiO2(実施例1)、水酸化アルミニウム(実施例2)、マイカ(実施例3)、焼成カオリン(実施例4)、天然親水性カオリン(実施例5)、木材粉末(実施例6)、及び炭酸カルシウム(実施例7)の粉末の300gのサンプルが、混合機(ミキサー)中、1及び3重量%の量で珪酸n−プロピル官能基ポリジメチルシロキサンA1の滴下により、各々処理された。これら処理された粉末が、次いで、1〜2時間、70℃〜120℃で更に乾かされた。これらの粉末の各々が、当初水に分散可能であった。これらの粉末の全てが、処理後に疎水性となり、水上に漂っている。
比較例C1:ビニルトリス(2−メトキシエトキシ)シラン、既知の疎水化剤
比較例C2:Dp12.6のヒドロキシ末端ポリジメチルシロキサン
実施例10:珪酸ビニル官能基ポリジメチルシロキサンA3
比較例C3:ビニルトリス(2−メトキシエトキシ)シラン、既知の疎水化剤
実施例11:珪酸n−プロピル官能基ポリジメチルシロキサンA1
実施例12:珪酸アミノプロピル官能基ポリジメチルシロキサンA6
比較例C4:ビニルトリス(2−メトキシエトキシ)シラン、既知の疎水化剤
実施例13:珪酸n−プロピル官能基ポリジメチルシロキサンA1
実施例14:珪酸ビニル官能基ポリジメチルシロキサンA3
比較例C5:ビニルトリス(2−メトキシエトキシ)シラン、既知の疎水化剤
比較例C6:Dp12.6のヒドロキシ末端ポリジメチルシロキサン
実施例15:珪酸n−プロピル官能基ポリジメチルシロキサンA1
実施例16:珪酸ビニル官能基ポリジメチルシロキサンA3
実施例17:珪酸アミノプロピル官能基ポリジメチルシロキサンA6
実施例18:珪酸メタクリロキシプロピル官能基ポリジメチルシロキサンA9
実施例19:珪酸グリシドキシプロピル官能基ポリジメチルシロキサンA10
実施例20:珪酸アミノプロピル官能基ポリジメチル/ビニルメチルシロキサン共重合体(コポリマー)A11
実施例21:珪酸ビニル官能基ポリジメチルシロキサンA12
実施例22:珪酸ビニル及び珪酸メトキシ官能基ポリジメチルシロキサンA13
ここで、ポリマーマトリックス中での相容性及び分散を向上させるための処理経由で、充填剤、色素及び/又は鉱物粉末を疎水化させることの有益さの例が続く。プラスチックマトリックス又はゴムマトリックス中での充填剤の相容性又は充填剤の相互作用と充填剤の分散との増加が、加工、並びに、種々の応用におけるプラスチック又はゴムの複合材料の充填の全体の仕上がり性能を向上させることが知られている(<<Handbook of Fillers>>、George Wypych、第2版、ChemTec出版及びプラスチックデザインライブラリー、1999年、545ページ〜549ページ及びこの中の参照)。これらの応用は、例えば、PVC又はPEにおける炭酸カルシウムに関し、建物の窓及び窓枠、ワイヤ及びケーブルの外装、包装フィルム及びバッグ;例えば、エポキシ、シリコーン、及びゴムにおけるシリカに関し、建物のフローリング、電気部品および電子部品、航空宇宙;例えば、ポリプロピレンにおけるタルク及びカオリンに関し、自動車バンパー、ダッシュボード、及び内装(インテリア);例えば、EVAにおけるATH及びMDHに関し、ワイヤ及びケーブル;例えば、ポリアミド、エポキシ、及びナイロンにおける繊維ガラスに関し、電気部品、プリント回路基板、自動車エンジンカバー;例えば、ポリプロピレンにおけるモンモリロナイトに関し、ヘルスケア及び医療、ワイヤ及びケーブルの外装であるが、これらに限定されない。
Claims (18)
- 珪素化合物を用いて直接表面処理された充填剤、色素又は鉱物粉末であって、前記珪素化合物が、式−SiR”(OR’)2又は−Si(OR’)3の少なくとも1つの末端基を両末端に有する分岐ポリジ有機シロキサンであり、式中、R”が、アルキル基、置換アルキル基、アルケニル基又はアリール基を表し、各R’が、1〜4個の炭素原子を有するアルキル基を表すことを特徴とする、処理された充填剤、色素又は鉱物粉末。
- 前記分岐ポリジ有機シロキサンが、式−SiR(OR’)2の少なくとも1つの末端基を有し、式中、Rが、アルキル基、アルケニル基又はアリール基を表し、各R’が、1〜4個の炭素原子を有するアルキル基を表すことを特徴とする、請求項1に記載の処理された充填剤、色素又は鉱物粉末。
- Rが、3〜8個の炭素原子を有するアルキル基を表すことを特徴とする、請求項2に記載の、処理された充填剤、色素又は鉱物粉末。
- 前記分岐ポリジ有機シロキサンの重合度が、4〜250シロキサン単位であることを特徴とする、請求項1〜3のいずれか一項に記載の処理された充填剤、色素又は鉱物粉末。
- 前記分岐ポリジ有機シロキサンが、25℃において2000Paよりも低い蒸気圧を有することを特徴とする、請求項1〜4のいずれか一項に記載の処理された充填剤、色素又は鉱物粉末。
- 前記分岐ポリジ有機シロキサンが、Si−アルコキシ基とシラノール基との縮合用触媒の存在下における、式R”Si(OR’)3のアルコキシシラン又は式Si(OR’)4のテトラアルコキシシランとヒドロキシル末端ポリジ有機シロキサンとの反応に由来することを特徴とする、請求項1〜5のいずれか一項に記載の処理された充填剤、色素又は鉱物粉末。
- 前記分岐ポリジ有機シロキサンが、前記ヒドロキシル末端ポリジ有機シロキサンの少なくとも3つのシラノール基と、式R”Si(OR’)3のアルコキシシラン又は式Si(OR’)4のテトラアルコキシシランの分子との反応に由来する分岐部位を含有することを特徴とする、請求項1〜6のいずれか一項に記載の処理された充填剤、色素又は鉱物粉末。
- 前記分岐ポリジ有機シロキサンが、分岐有機珪素樹脂及びSi−アルコキシ基とシラノール基との縮合用触媒の存在下における、式R”Si(OR’)3のアルコキシシラン及び/又は式Si(OR’)4のテトラアルコキシシランとヒドロキシル末端ポリジ有機シロキサンとの反応に由来する分岐部位を含有することを特徴とする、請求項1〜6のいずれか一項に記載の処理された充填剤、色素又は鉱物粉末。
- 前記分岐ポリジ有機シロキサンが、式R”Si(OR’)3のアルコキシシラン及び/又は式Si(OR’)4のテトラアルコキシシランと分岐ヒドロキシル末端ポリジ有機シロキサンとの反応に由来する分岐部位を含有することを特徴とする、請求項1〜6のいずれか一項に記載の処理された充填剤、色素又は鉱物粉末。
- 珪素化合物を用いる、充填剤、色素又は鉱物粉末の表面処理方法であって、前記珪素化合物を用いて前記充填剤、色素又は鉱物粉末を直接表面処理し、前記珪素化合物が、式−SiR”(OR’)2又は式−Si(OR’)3の少なくとも1つの末端基を両末端に有する分岐ポリジ有機シロキサンであり、式中、R”が、アルキル基、置換アルキル基、アルケニル基又はアリール基を表し、各R’が、1〜4個の炭素原子を有するアルキル基を表すことを特徴とする、方法。
- 前記充填剤、色素又は鉱物粉末が、前記分岐ポリジ有機シロキサンと、アミノシラン又はアミノシロキサンとの混合物を用いて処理されることを特徴とする、請求項10に記載の方法。
- 前記充填剤、色素又は鉱物粉末が、前記分岐ポリジ有機シロキサンと、Si−OH基又はSi−アルコキシ基を含有する非線状有機珪素樹脂との混合物を用いて処理されることを特徴とする、請求項10又は請求項11に記載の方法。
- 充填剤、色素又は鉱物粉末をより疎水性とする珪素化合物の使用であって、前記珪素化合物を用いて前記充填剤、色素又は鉱物粉末を直接表面処理し、前記珪素化合物が、式−SiR”(OR’)2又は式−Si(OR’)3の少なくとも1つの末端基を両末端に有する分岐ポリジ有機シロキサンであり、式中、R”が、アルキル基、置換アルキル基、アルケニル基又はアリール基を表し、各R’が、1〜4個の炭素原子を有するアルキル基を表すことを特徴とする、使用。
- プラスチック又はゴム組成物であって、前記プラスチック又はゴムが、請求項1〜9のいずれか一項において定義されたとおりの充填剤又は色素を含有することを特徴とする、プラスチック又はゴム組成物。
- プラスチック又はゴム組成物の製造方法であって、請求項1〜9のいずれか一項において定義されたとおりの充填剤又は色素が、プラスチック又はゴムマトリックス材料と混合されることを特徴とする、プラスチック又はゴム組成物の製造方法。
- プラスチック又はゴム組成物の製造方法であって、有機プラスチック又はゴムマトリックス材料が、充填剤又は色素、及び式−SiR”(OR’)2又は式−Si(OR’)3の少なくとも1つの末端基を両末端に有する分岐ポリジ有機シロキサンと直接混合され、式中、R”が、アルキル基、置換アルキル基、アルケニル基又はアリール基を表し、各R’が、1〜4個の炭素原子を有するアルキル基を表すことを特徴とする、プラスチック又はゴム組成物の製造方法。
- 前記分岐ポリジ有機シロキサンが、式−SiR(OR’)2の少なくとも1つの末端基を有し、式中、Rが、アルキル基、アルケニル基又はアリール基を表し、各R’が、1〜4個の炭素原子を有するアルキル基を表すことを特徴とする、請求項16に記載の方法。
- 化学加工又は冶金加工における加工助剤としての、請求項1〜9のいずれか一項において定義されたとおりの鉱物粉末の使用。
Applications Claiming Priority (5)
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GB0618186.1 | 2006-09-18 | ||
GB0618186A GB0618186D0 (en) | 2006-09-18 | 2006-09-18 | Organopolysiloxanes for treating fillers and pigments |
GB0709438A GB0709438D0 (en) | 2007-05-17 | 2007-05-17 | Fillers, pigments and mineral powders treated with organopolysiloxanes |
GB0709438.6 | 2007-05-17 | ||
PCT/EP2007/059803 WO2008034806A1 (en) | 2006-09-18 | 2007-09-17 | Fillers, pigments and mineral powders treated with organopolysiloxanes |
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JP2010503759A JP2010503759A (ja) | 2010-02-04 |
JP2010503759A5 JP2010503759A5 (ja) | 2010-06-17 |
JP5232153B2 true JP5232153B2 (ja) | 2013-07-10 |
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US (1) | US9115285B2 (ja) |
EP (1) | EP2064291B1 (ja) |
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2007
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- 2007-09-17 US US12/441,436 patent/US9115285B2/en active Active
- 2007-09-17 WO PCT/EP2007/059803 patent/WO2008034806A1/en active Application Filing
- 2007-09-17 EP EP07820270.2A patent/EP2064291B1/en not_active Revoked
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EP2064291A1 (en) | 2009-06-03 |
JP2010503759A (ja) | 2010-02-04 |
US20090318614A1 (en) | 2009-12-24 |
US9115285B2 (en) | 2015-08-25 |
EP2064291B1 (en) | 2017-02-22 |
WO2008034806A1 (en) | 2008-03-27 |
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