JP5602837B2 - 粒子状ナノコンポジット材料を製造する方法 - Google Patents
粒子状ナノコンポジット材料を製造する方法 Download PDFInfo
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- JP5602837B2 JP5602837B2 JP2012509051A JP2012509051A JP5602837B2 JP 5602837 B2 JP5602837 B2 JP 5602837B2 JP 2012509051 A JP2012509051 A JP 2012509051A JP 2012509051 A JP2012509051 A JP 2012509051A JP 5602837 B2 JP5602837 B2 JP 5602837B2
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- polymerization
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- 239000000463 material Substances 0.000 title claims description 131
- 239000002114 nanocomposite Substances 0.000 title claims description 106
- 238000004519 manufacturing process Methods 0.000 title claims description 17
- 239000000178 monomer Substances 0.000 claims description 175
- 238000006116 polymerization reaction Methods 0.000 claims description 111
- 229910052751 metal Inorganic materials 0.000 claims description 87
- 239000002184 metal Substances 0.000 claims description 87
- 239000002245 particle Substances 0.000 claims description 81
- 238000000034 method Methods 0.000 claims description 66
- 239000004094 surface-active agent Substances 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 229910052760 oxygen Inorganic materials 0.000 claims description 49
- 229910052752 metalloid Inorganic materials 0.000 claims description 47
- 150000002738 metalloids Chemical class 0.000 claims description 47
- 229910052799 carbon Inorganic materials 0.000 claims description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 239000011236 particulate material Substances 0.000 claims description 38
- 229910052710 silicon Inorganic materials 0.000 claims description 36
- -1 Selected from CN Inorganic materials 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 33
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- 125000000129 anionic group Chemical group 0.000 claims description 30
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- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 229910052718 tin Inorganic materials 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
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- 239000000010 aprotic solvent Substances 0.000 claims description 24
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- 239000003586 protic polar solvent Substances 0.000 claims description 24
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- 239000001301 oxygen Substances 0.000 claims description 23
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
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- 125000005376 alkyl siloxane group Chemical group 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical class [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000012071 phase Substances 0.000 description 125
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- 239000000047 product Substances 0.000 description 22
- 150000002431 hydrogen Chemical class 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
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- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 9
- 230000001681 protective effect Effects 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
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- 125000005843 halogen group Chemical group 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
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- 239000000843 powder Substances 0.000 description 7
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- 239000000377 silicon dioxide Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910019142 PO4 Inorganic materials 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- 238000005054 agglomeration Methods 0.000 description 6
- 230000002776 aggregation Effects 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 6
- 238000007046 ethoxylation reaction Methods 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 235000021317 phosphate Nutrition 0.000 description 6
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- 230000000052 comparative effect Effects 0.000 description 5
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- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 150000001447 alkali salts Chemical class 0.000 description 4
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
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- 150000002989 phenols Chemical group 0.000 description 4
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- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
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- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- BJZIXRIEVONTPV-UHFFFAOYSA-N tetrakis(furan-2-ylmethyl) silicate Chemical compound C=1C=COC=1CO[Si](OCC=1OC=CC=1)(OCC=1OC=CC=1)OCC1=CC=CO1 BJZIXRIEVONTPV-UHFFFAOYSA-N 0.000 description 1
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005389 trialkylsiloxy group Chemical group 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 229920003176 water-insoluble polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/14—Organic medium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/005—Reinforced macromolecular compounds with nanosized materials, e.g. nanoparticles, nanofibres, nanotubes, nanowires, nanorods or nanolayered materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2361/00—Characterised by the use of condensation polymers of aldehydes or ketones; Derivatives of such polymers
- C08J2361/04—Condensation polymers of aldehydes or ketones with phenols only
- C08J2361/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Nanotechnology (AREA)
- Materials Engineering (AREA)
- General Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Composite Materials (AREA)
- Crystallography & Structural Chemistry (AREA)
- Physics & Mathematics (AREA)
- Manufacturing & Machinery (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Graft Or Block Polymers (AREA)
- Polyethers (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09159814.4 | 2009-05-08 | ||
| EP09159814 | 2009-05-08 | ||
| PCT/EP2010/056265 WO2010128144A1 (de) | 2009-05-08 | 2010-05-07 | Verfahren zur herstellung eines partikelförmigen nanokompositmaterials |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012526168A JP2012526168A (ja) | 2012-10-25 |
| JP2012526168A5 JP2012526168A5 (enExample) | 2013-06-27 |
| JP5602837B2 true JP5602837B2 (ja) | 2014-10-08 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012509051A Expired - Fee Related JP5602837B2 (ja) | 2009-05-08 | 2010-05-07 | 粒子状ナノコンポジット材料を製造する方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8680203B2 (enExample) |
| EP (1) | EP2427466A1 (enExample) |
| JP (1) | JP5602837B2 (enExample) |
| KR (1) | KR20120044934A (enExample) |
| CN (1) | CN102459285A (enExample) |
| CA (1) | CA2759166A1 (enExample) |
| WO (1) | WO2010128144A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2754711A1 (en) * | 2009-04-03 | 2010-10-07 | Basf Se | Electroactive material, and use thereof in anodes for lithium-ion cells |
| JP2011184503A (ja) * | 2010-03-05 | 2011-09-22 | Sumitomo Chemical Co Ltd | 熱可塑性エラストマー組成物 |
| US8536264B2 (en) * | 2010-04-02 | 2013-09-17 | The Goodyear Tire & Rubber Company | Pneumatic tire and rubber composition containing twin polymerization structures |
| GB2487142B (en) * | 2010-05-26 | 2012-12-12 | Hiok Nam Tay | Auto-focus image system |
| EP2665764A2 (de) | 2011-01-19 | 2013-11-27 | Basf Se | Verfahren zur herstellung eines kompositmaterials |
| US9099744B2 (en) | 2011-03-31 | 2015-08-04 | Basf Se | Particulate porous carbon material and use thereof in lithium cells |
| CN103459312A (zh) * | 2011-03-31 | 2013-12-18 | 巴斯夫欧洲公司 | 颗粒状多孔碳材料及其在锂电池中的应用 |
| EP2807209A4 (de) * | 2012-01-23 | 2015-09-02 | Basf Se | Kompositmaterial, dessen herstellung und dessen verwendung in separatoren für elektrochemische zellen |
| US8865858B2 (en) | 2012-06-26 | 2014-10-21 | Basf Se | Process for producing a composite material |
| WO2014001273A1 (de) | 2012-06-26 | 2014-01-03 | Basf Se | Verfahren zur herstellung eines kompositmaterials |
| WO2014009451A1 (de) | 2012-07-12 | 2014-01-16 | Basf Se | Verfahren zur herstellung von kompositmaterialien |
| WO2014049103A1 (de) | 2012-09-28 | 2014-04-03 | Basf Se | Verfahren zur herstellung von kompositmaterialien |
| WO2015086461A1 (de) | 2013-12-13 | 2015-06-18 | Basf Se | Stickstoff-haltige kompositmaterialien, deren herstellung und verwendung |
| JP6468021B2 (ja) * | 2015-03-20 | 2019-02-13 | 株式会社リコー | 立体造形用粉末材料、及び立体造形用材料セット、並びに、立体造形物、立体造形物の製造方法及び製造装置 |
| WO2017066757A1 (en) * | 2015-10-15 | 2017-04-20 | William Marsh Rice University | Microwave induced curing of nanomaterials for geological formation reinforcement |
| CN114026102A (zh) | 2019-07-18 | 2022-02-08 | 巴斯夫欧洲公司 | 孪生单体组合物及其介电膜 |
| CN111333853A (zh) * | 2020-03-17 | 2020-06-26 | 北京科技大学 | 基于mof@金属纳米颗粒@cof复合材料的制备方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3230289A1 (de) | 1982-08-14 | 1984-02-16 | Bayer Ag, 5090 Leverkusen | Herstellung von pharmazeutischen oder kosmetischen dispersionen |
| CA1339436C (en) | 1987-10-02 | 1997-09-02 | Rohm And Haas Company | Non-aqueous dispersion for alkyd formulations and method of manufacture |
| WO2001012678A1 (en) | 1999-08-13 | 2001-02-22 | Solutia Inc. | Methods for the preparation of polyamide nanocomposite compositions by in situ polymerization |
| EP1403332A1 (en) | 2002-09-30 | 2004-03-31 | Rohm And Haas Company | Nonaqueous compositions comprising polymernanoparticles (PNP) |
| DE10261289A1 (de) | 2002-12-27 | 2004-07-15 | Sustech Gmbh & Co. Kg | Verfahren zur Herstellung von Polyalkyl(halb)metallaten |
| DE102005042138A1 (de) | 2005-09-05 | 2007-03-08 | Deutsches Wollforschungsinstitut An Der Rwth Aachen E.V. | Verfahren zur Herstellung von Verbundwerkstoffen |
| DE102006025848A1 (de) * | 2006-03-29 | 2007-10-04 | Byk-Chemie Gmbh | Herstellung von Nanopartikeln, insbesondere Nanopartikelkompositen, ausgehend von Pulveragglomeraten |
| DE102007063297A1 (de) * | 2007-12-27 | 2009-07-02 | Merck Patent Gmbh | Poröse monolithische Materialien |
| DE102007063284A1 (de) * | 2007-12-27 | 2009-07-02 | Basf Se | Spiroverbindungen |
| CN101423639B (zh) * | 2008-12-09 | 2011-02-02 | 中山大学 | 一种PPR/SiO2纳米复合材料及其制备方法 |
| KR20110136889A (ko) * | 2009-04-03 | 2011-12-21 | 바스프 에스이 | 복합 물질의 제조 방법 |
-
2010
- 2010-05-07 CA CA2759166A patent/CA2759166A1/en not_active Abandoned
- 2010-05-07 US US13/319,414 patent/US8680203B2/en not_active Expired - Fee Related
- 2010-05-07 WO PCT/EP2010/056265 patent/WO2010128144A1/de not_active Ceased
- 2010-05-07 EP EP10717172A patent/EP2427466A1/de not_active Withdrawn
- 2010-05-07 CN CN2010800308578A patent/CN102459285A/zh active Pending
- 2010-05-07 JP JP2012509051A patent/JP5602837B2/ja not_active Expired - Fee Related
- 2010-05-07 KR KR1020117029268A patent/KR20120044934A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CA2759166A1 (en) | 2010-11-11 |
| US20120052300A1 (en) | 2012-03-01 |
| EP2427466A1 (de) | 2012-03-14 |
| KR20120044934A (ko) | 2012-05-08 |
| WO2010128144A1 (de) | 2010-11-11 |
| CN102459285A (zh) | 2012-05-16 |
| JP2012526168A (ja) | 2012-10-25 |
| US8680203B2 (en) | 2014-03-25 |
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