JP6257519B2 - 安定したナノ粒子懸濁液およびその製造法 - Google Patents
安定したナノ粒子懸濁液およびその製造法 Download PDFInfo
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- 239000000725 suspension Substances 0.000 title claims description 51
- 238000000034 method Methods 0.000 title claims description 13
- 230000008569 process Effects 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000002105 nanoparticle Substances 0.000 title description 15
- 239000002270 dispersing agent Substances 0.000 claims description 31
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 20
- 239000006185 dispersion Substances 0.000 claims description 14
- 239000000654 additive Substances 0.000 claims description 12
- 239000010954 inorganic particle Substances 0.000 claims description 12
- 239000007900 aqueous suspension Substances 0.000 claims description 11
- 239000004408 titanium dioxide Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 150000001414 amino alcohols Chemical class 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims 2
- 239000011159 matrix material Substances 0.000 claims 1
- 239000002245 particle Substances 0.000 description 21
- 238000009826 distribution Methods 0.000 description 10
- 239000011049 pearl Substances 0.000 description 5
- IOAOAKDONABGPZ-UHFFFAOYSA-N 2-amino-2-ethylpropane-1,3-diol Chemical compound CCC(N)(CO)CO IOAOAKDONABGPZ-UHFFFAOYSA-N 0.000 description 4
- 229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 4
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 4
- 241001648788 Margarodidae Species 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- 239000003139 biocide Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000035699 permeability Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000518 rheometry Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- -1 electronics Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229940094522 laponite Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229910001463 metal phosphate Inorganic materials 0.000 description 1
- 229910052914 metal silicate Inorganic materials 0.000 description 1
- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 239000011941 photocatalyst Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000006557 surface reaction Methods 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
- C03C17/006—Surface treatment of glass, not in the form of fibres or filaments, by coating with materials of composite character
- C03C17/007—Surface treatment of glass, not in the form of fibres or filaments, by coating with materials of composite character containing a dispersed phase, e.g. particles, fibres or flakes, in a continuous phase
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/002—Inorganic compounds
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C2217/00—Coatings on glass
- C03C2217/20—Materials for coating a single layer on glass
- C03C2217/21—Oxides
- C03C2217/212—TiO2
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C2217/00—Coatings on glass
- C03C2217/40—Coatings comprising at least one inhomogeneous layer
- C03C2217/42—Coatings comprising at least one inhomogeneous layer consisting of particles only
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C2218/00—Methods for coating glass
- C03C2218/10—Deposition methods
- C03C2218/11—Deposition methods from solutions or suspensions
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/14—Derivatives of phosphoric acid
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
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- Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Geochemistry & Mineralogy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Composite Materials (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
- Colloid Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Paints Or Removers (AREA)
Description
本発明は、ナノ粒子、殊に二酸化チタン粒子の安定した高濃縮された水性懸濁液、その製造法および例えば被覆剤もしくは含浸剤として、または有機マトリックスもしくは無機マトリックスにおける添加剤としての当該懸濁液の使用に関する。
ナノ粒子(粒度 典型的には100nm未満)は、ナノテクノロジー添加剤(Nanoadditive)として、例えば被覆剤、プラスチック、光学製品、電子機器、セラミック、特殊化学品等において、多大な技術革新の潜在性をもっている。その際に、前記ナノ粒子は、例えば光触媒、UV吸収剤、耐摩耗剤、充填剤として、または表面機能化のためにさまざまな機能をもつことができる。
本発明の課題は、簡単で安価に製造することができかつ高い剪断速度の場合でも重大な粘度上昇を示さない、50質量%を上回る固体濃度を有する、ナノ粒子の安定した水性懸濁液を提供することである。
pH値、温度、質量%または容量%での濃度等に関連する、以下に開示された記載は、当業者に公知のそれぞれの測定精度の範囲内にある全ての値が一緒に含まれていると理解すべきである。
以下、本発明を例示的に記載するが、それによって本発明は、限定されるものではない。
例1
1.脱イオン水 318.0g、
2.Rheolate 420(レオロジー添加剤) 3.5g、
3.Byk 023(消泡剤) 2.0g、
4.Solplus D540(第1の分散剤) 120.0g、
5.Acticide IMS(殺生剤) 1.0g、
6.AMP 90(第2の分散剤) 55.5g、
7.ナノスケール二酸化チタン KRONOClean7000 500.0g
総和 1000.0g。
1.脱イオン水 402.2g、
2.Laponite SL 25(レオロジー添加剤) 12.0g、
3.Byk 023(消泡剤) 2.0g、
4.Solplus D541(第1の分散剤) 124.0g、
5.Acticide IMS(殺生剤) 1.0g、
6.AEPD VOX 1000(第2の分散剤) 58.8g、
7.ナノスケール二酸化チタン KRONOClean7000 400.0g
総和 1000.0g。
ミル容積は、125mlであり、粉砕パール(ZrO2パール、0.4〜0.6mm)の容積は、空隙容積を含めて100mlである。1 lの懸濁液を3000〜5000rpmおよび700Wのエネルギー入力で10時間分散させ、その際に温度を50℃未満に保持した。
Claims (10)
- 固体濃度が50質量%を上回る、150nm未満であるナノスケール無機粒子の水性懸濁液であって、
ポリマーのアルコキシレートをベースとする第1の分散剤およびアミノアルコールの群からの第2の分散剤が含まれ、ナノスケール無機粒子として二酸化チタンが使用され、ポリマーのアルコキシレートが、アルカリ金属又はアルカリ土類金属の(ポリ)アルコールの塩であり、かつホスフェートにより官能化されたアルコキシレートであり、前記分散剤の全体量がナノスケール無機粒子に対して3〜40質量%であり、ナノスケール無機粒子の濃度が懸濁液に対して70質量%までであり、かつ少なくとも5のpHで安定していることを特徴とする、前記水性懸濁液。 - 前記懸濁液が熱処理に掛けられることを特徴とする、請求項1記載の水性懸濁液。
- 熱処理後の湿分が5質量%未満であることを特徴とする、請求項2記載の水性懸濁液。
- 固体濃度が50質量%を上回る、150nm未満であるナノスケール無機粒子の水性懸濁液を製造する方法であって、
ポリマーのアルコキシレートをベースとする第1の分散剤およびアミノアルコールの群からの第2の分散剤を使用し、ナノスケール無機粒子として二酸化チタンが使用され、ポリマーのアルコキシレートが、アルカリ金属又はアルカリ土類金属の(ポリ)アルコールの塩であり、かつホスフェートにより官能化されたアルコキシレートであり、前記分散剤の全体量をナノスケール無機粒子に対して3〜40質量%で添加し、ナノスケール無機粒子の濃度を懸濁液に対して70質量%までに調節し、かつ少なくとも5のpHで安定していることを特徴とする、前記方法。 - 第1の工程においてディソルバーで予備分散させることを特徴とする、請求項4記載の方法。
- 攪拌型ボールミル中で分散させることを特徴とする、請求項4または5記載の方法。
- 引続き前記懸濁液の含水量を熱処理によって5質量%未満に減少させることを特徴とする、請求項4から6までのいずれか1項に記載の方法。
- 熱処理された懸濁液を引き続き水中に再分散させることを特徴とする、請求項7記載の方法。
- 撹拌型ボールミルの粉砕ボールは、0.1〜1.0mmの直径を有することを特徴とする、請求項6に記載の方法。
- 無機表面もしくは有機表面への被覆剤または含浸剤として、または有機マトリックスもしくは無機マトリックスにおける添加剤としての、請求項1から3までのいずれか1項に記載の水性懸濁液の使用。
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Application Number | Priority Date | Filing Date | Title |
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DE102011114363.0 | 2011-09-27 | ||
DE102011114363A DE102011114363A1 (de) | 2011-09-27 | 2011-09-27 | Stabile nanopartikuläre Suspension und Verfahren zur Herstellung |
PCT/EP2012/003996 WO2013045071A2 (de) | 2011-09-27 | 2012-09-25 | Stabile nanopartikuläre suspension und verfahren zur herstellung |
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JP2015501272A JP2015501272A (ja) | 2015-01-15 |
JP6257519B2 true JP6257519B2 (ja) | 2018-01-10 |
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Country Status (10)
Country | Link |
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US (1) | US9498760B2 (ja) |
EP (1) | EP2760574B1 (ja) |
JP (1) | JP6257519B2 (ja) |
KR (1) | KR101819444B1 (ja) |
CN (1) | CN103842065A (ja) |
BR (1) | BR112014006701B1 (ja) |
DE (1) | DE102011114363A1 (ja) |
ES (1) | ES2618916T3 (ja) |
MY (1) | MY169360A (ja) |
WO (1) | WO2013045071A2 (ja) |
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TW201435830A (zh) * | 2012-12-11 | 2014-09-16 | 3M Innovative Properties Co | 不顯眼之光學標籤及其方法 |
GB2534239B (en) * | 2015-03-26 | 2017-04-19 | Solar Fluidics Pte Ltd | Solar energy system |
US11819580B2 (en) | 2016-10-18 | 2023-11-21 | PurWorld Technologies LLC | Method of chemically disinfecting a vehicle |
DE102018103526A1 (de) | 2018-02-16 | 2019-08-22 | Friedrich-Alexander-Universität Erlangen-Nürnberg | Stabilisierte Suspension und Verfahren zur Herstellung einer stabilisierten Suspension |
CN117088407B (zh) * | 2023-10-20 | 2024-01-02 | 琥崧科技集团股份有限公司 | 一种纳米二氧化钛及其制备方法和应用 |
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US4978396A (en) * | 1989-05-12 | 1990-12-18 | Kerr-Mcgee Chemical Corporation | Process for preparing high solids slurries |
GB9524475D0 (en) * | 1995-11-30 | 1996-01-31 | Zeneca Ltd | Compound preparation and use |
JP3080162B2 (ja) * | 1998-01-27 | 2000-08-21 | 日本パーカライジング株式会社 | 酸化チタンゾルおよびその製造方法 |
WO2005107927A2 (en) * | 2004-04-29 | 2005-11-17 | Solucorp Industries, Ltd. | Air pollution control |
DE102004037118A1 (de) * | 2004-07-30 | 2006-03-23 | Degussa Ag | Titandioxid enthaltende Dispersion |
WO2008045984A1 (en) * | 2006-10-12 | 2008-04-17 | Suncolor Coporation | Polymeric composition |
DE102006057903A1 (de) * | 2006-12-08 | 2008-06-12 | Evonik Degussa Gmbh | Titandioxid enthaltende Dispersion |
JP5774980B2 (ja) * | 2008-04-07 | 2015-09-09 | エコラボ インコーポレイティド | 超高濃度液体脱脂組成物 |
US20100110551A1 (en) * | 2008-10-31 | 2010-05-06 | 3M Innovative Properties Company | Light extraction film with high index backfill layer and passivation layer |
CN102361686B (zh) | 2009-03-23 | 2014-10-15 | 瓦林格光催化股份有限公司 | 使用具有微米级珠的珠磨机制备具有保持结晶度的二氧化钛纳米颗粒胶态悬浮体 |
WO2011022582A1 (en) * | 2009-08-21 | 2011-02-24 | Lubrizol Advanced Materials, Inc. | Hydrolytically stable polyurethane nanocomposites |
CN102002260B (zh) * | 2010-10-21 | 2013-08-14 | 施丽萍 | Pet专用纳米稀土氧化物分散悬浮液的制备方法 |
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2011
- 2011-09-27 DE DE102011114363A patent/DE102011114363A1/de not_active Withdrawn
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Publication number | Publication date |
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KR20140069159A (ko) | 2014-06-09 |
EP2760574B1 (de) | 2017-02-01 |
BR112014006701B1 (pt) | 2020-09-29 |
US9498760B2 (en) | 2016-11-22 |
JP2015501272A (ja) | 2015-01-15 |
CN103842065A (zh) | 2014-06-04 |
ES2618916T3 (es) | 2017-06-22 |
EP2760574A2 (de) | 2014-08-06 |
MY169360A (en) | 2019-03-26 |
KR101819444B1 (ko) | 2018-01-17 |
DE102011114363A1 (de) | 2013-03-28 |
WO2013045071A2 (de) | 2013-04-04 |
BR112014006701A2 (pt) | 2017-03-28 |
WO2013045071A3 (de) | 2013-08-01 |
US20130074731A1 (en) | 2013-03-28 |
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