CA2599679C - Nanoparticle/vinyl polymer composites - Google Patents
Nanoparticle/vinyl polymer composites Download PDFInfo
- Publication number
- CA2599679C CA2599679C CA2599679A CA2599679A CA2599679C CA 2599679 C CA2599679 C CA 2599679C CA 2599679 A CA2599679 A CA 2599679A CA 2599679 A CA2599679 A CA 2599679A CA 2599679 C CA2599679 C CA 2599679C
- Authority
- CA
- Canada
- Prior art keywords
- polymer
- nanoparticles
- vinyl
- monomers
- vinyl polymer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000002105 nanoparticle Substances 0.000 title claims abstract description 105
- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 89
- 239000002131 composite material Substances 0.000 title claims abstract description 16
- 229920000642 polymer Polymers 0.000 claims abstract description 92
- 239000000178 monomer Substances 0.000 claims abstract description 87
- 239000006185 dispersion Substances 0.000 claims abstract description 75
- 238000006243 chemical reaction Methods 0.000 claims abstract description 57
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 42
- 238000010528 free radical solution polymerization reaction Methods 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 39
- 239000000203 mixture Substances 0.000 claims abstract description 39
- 238000012662 bulk polymerization Methods 0.000 claims abstract description 36
- 239000012736 aqueous medium Substances 0.000 claims abstract description 21
- 230000008569 process Effects 0.000 claims abstract description 18
- 230000000977 initiatory effect Effects 0.000 claims abstract description 5
- 239000002245 particle Substances 0.000 claims description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 239000004094 surface-active agent Substances 0.000 claims description 11
- 239000000377 silicon dioxide Substances 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 3
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 claims description 3
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 238000005259 measurement Methods 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 239000004927 clay Substances 0.000 claims 1
- 229910052570 clay Inorganic materials 0.000 claims 1
- 239000000853 adhesive Substances 0.000 abstract description 5
- 230000001070 adhesive effect Effects 0.000 abstract description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 58
- -1 i.e. Substances 0.000 description 42
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 12
- 230000002708 enhancing effect Effects 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- 238000007720 emulsion polymerization reaction Methods 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 10
- 239000004615 ingredient Substances 0.000 description 9
- 239000004014 plasticizer Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 239000011246 composite particle Substances 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
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- 125000000524 functional group Chemical group 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 4
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
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- 150000001993 dienes Chemical class 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Chemical class 0.000 description 4
- SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical compound C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 description 4
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- 125000000129 anionic group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
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- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229910000000 metal hydroxide Inorganic materials 0.000 description 3
- 150000004692 metal hydroxides Chemical class 0.000 description 3
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- IBDVWXAVKPRHCU-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC(=O)C(C)=C IBDVWXAVKPRHCU-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
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- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
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- 229910019142 PO4 Inorganic materials 0.000 description 2
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 2
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- IPJKJLXEVHOKSE-UHFFFAOYSA-L manganese dihydroxide Chemical compound [OH-].[OH-].[Mn+2] IPJKJLXEVHOKSE-UHFFFAOYSA-L 0.000 description 1
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- 150000001247 metal acetylides Chemical class 0.000 description 1
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- 125000005394 methallyl group Chemical group 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
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- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
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- 239000002114 nanocomposite Substances 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
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- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 1
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
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- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
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- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical group [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
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- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
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- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
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- SZHIIIPPJJXYRY-UHFFFAOYSA-M sodium;2-methylprop-2-ene-1-sulfonate Chemical compound [Na+].CC(=C)CS([O-])(=O)=O SZHIIIPPJJXYRY-UHFFFAOYSA-M 0.000 description 1
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
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- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
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- MTPVUVINMAGMJL-UHFFFAOYSA-N trimethyl(1,1,2,2,2-pentafluoroethyl)silane Chemical compound C[Si](C)(C)C(F)(F)C(F)(F)F MTPVUVINMAGMJL-UHFFFAOYSA-N 0.000 description 1
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- WGEATSXPYVGFCC-UHFFFAOYSA-N zinc ferrite Chemical compound O=[Zn].O=[Fe]O[Fe]=O WGEATSXPYVGFCC-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/20—Compounding polymers with additives, e.g. colouring
- C08J3/205—Compounding polymers with additives, e.g. colouring in the presence of a continuous liquid phase
- C08J3/21—Compounding polymers with additives, e.g. colouring in the presence of a continuous liquid phase the polymer being premixed with a liquid phase
- C08J3/212—Compounding polymers with additives, e.g. colouring in the presence of a continuous liquid phase the polymer being premixed with a liquid phase and solid additives
-
- 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
- C08F2/16—Aqueous medium
- C08F2/18—Suspension polymerisation
-
- 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
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/20—Compounding polymers with additives, e.g. colouring
- C08J3/205—Compounding polymers with additives, e.g. colouring in the presence of a continuous liquid phase
-
- 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
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/20—Compounding polymers with additives, e.g. colouring
- C08J3/205—Compounding polymers with additives, e.g. colouring in the presence of a continuous liquid phase
- C08J3/2053—Compounding polymers with additives, e.g. colouring in the presence of a continuous liquid phase the additives only being premixed with a liquid phase
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymerisation Methods In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Graft Or Block Polymers (AREA)
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| US66363505P | 2005-03-17 | 2005-03-17 | |
| US60/663,635 | 2005-03-17 | ||
| PCT/US2006/010079 WO2006099630A1 (en) | 2005-03-17 | 2006-03-16 | Nanoparticle/vinyl polymer composites |
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| CA2599679A1 CA2599679A1 (en) | 2006-09-21 |
| CA2599679C true CA2599679C (en) | 2014-07-29 |
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| EP (1) | EP1858964B1 (https=) |
| JP (1) | JP5268144B2 (https=) |
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| CA (1) | CA2599679C (https=) |
| WO (1) | WO2006099630A1 (https=) |
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| DE102006014088A1 (de) * | 2006-03-24 | 2007-09-27 | Basf Coatings Ag | Copolymerisate olefinish ungesättigter Monomere, Verfahren zu ihrer Herstellung und ihre Verwendung |
| EP1837362A1 (de) * | 2006-03-24 | 2007-09-26 | Solvay Infra Bad Hönningen GmbH | Durch Coploymerisate olefinisch ungesättigter Monomere modifizierte Partikel |
| GB0612803D0 (en) * | 2006-06-28 | 2006-08-09 | Lucite Int Uk Ltd | Polymeric composition |
| WO2009150931A1 (ja) * | 2008-06-12 | 2009-12-17 | 財団法人川村理化学研究所 | 有機無機複合体分散液及びそれを用いて製造される細胞培養基材、及びそれらの製造方法 |
| US8216961B2 (en) | 2008-08-27 | 2012-07-10 | Korea University Research And Business Foundation | Nanoparticles including metal oxide having catalytic activity |
| US20100054988A1 (en) * | 2008-08-29 | 2010-03-04 | Kwangyeol Lee | Photocatalytic nanocapsule and fiber for water treatment |
| MY156540A (en) * | 2008-10-13 | 2016-02-26 | Basf Se | Producing a monofilament and use thereof |
| US8309489B2 (en) * | 2009-06-18 | 2012-11-13 | University Of Central Florida Research Foundation, Inc. | Thermally stable nanoparticles on supports |
| BR112012003817A2 (pt) * | 2009-08-21 | 2016-03-22 | Lubrizol Advanced Mat Inc | nanocompósito de poliéster-poliuretano hidroliticamente estável, dispersão aquosa do mesmo, e, processo para preparar a dispersão aquosa |
| EP2311909A1 (de) * | 2009-10-16 | 2011-04-20 | Nanoresins AG | Hybrid-Partikel von Polymeren und Nanopartikeln |
| JP5968310B2 (ja) * | 2010-06-24 | 2016-08-10 | スリーエム イノベイティブ プロパティズ カンパニー | 有機乳化剤を含まない重合性組成物、並びにそのポリマー及び製造方法 |
| WO2012102187A1 (ja) * | 2011-01-25 | 2012-08-02 | 日立化成工業株式会社 | Ｃｍｐ研磨液及びその製造方法、複合粒子の製造方法、並びに基体の研磨方法 |
| CN103814070B (zh) * | 2011-09-09 | 2016-08-24 | 沙特基础工业公司 | 遇水膨胀的聚合物小球 |
| EP2857350A1 (en) * | 2013-09-10 | 2015-04-08 | ESPCI Innov | Use of nanoparticles for gluing gels |
| US10260195B1 (en) | 2014-05-08 | 2019-04-16 | Precision Textiles LLC | Nanoclay-modified fabrics for flame retardation |
| CN109207244B (zh) * | 2017-06-30 | 2021-10-26 | 北京市建筑工程研究院有限责任公司 | 一种混凝土预制构件用水性脱模剂 |
| CN115989250A (zh) * | 2020-07-08 | 2023-04-18 | 陶氏环球技术有限责任公司 | 用于制备聚合物多元醇的熔融分散方法 |
| CN115160707B (zh) * | 2022-07-01 | 2023-09-01 | 湖南莞商工业科技有限公司 | 一种聚氯乙烯木塑复合材料及其制备方法 |
| US12042056B2 (en) | 2022-07-12 | 2024-07-23 | Precision Textiles LLC | Mattress cover and related method |
| WO2025053218A1 (ja) * | 2023-09-08 | 2025-03-13 | 日信化学工業株式会社 | 水性分散体、水性インキ、記録媒体、及び、水性分散体を生産する方法 |
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| US6912610B2 (en) * | 2003-03-28 | 2005-06-28 | Emulex Design & Manufacturing Corporation | Hardware assisted firmware task scheduling and management |
| US7627808B2 (en) * | 2003-06-13 | 2009-12-01 | Microsoft Corporation | Computer media synchronization player |
| US8190722B2 (en) * | 2003-06-30 | 2012-05-29 | Randy Oyadomari | Synchronization of timestamps to compensate for communication latency between devices |
-
2006
- 2006-03-16 WO PCT/US2006/010079 patent/WO2006099630A1/en not_active Ceased
- 2006-03-16 CN CN2006800085821A patent/CN101142263B/zh not_active Expired - Fee Related
- 2006-03-16 EP EP06739031A patent/EP1858964B1/en not_active Expired - Lifetime
- 2006-03-16 JP JP2008502146A patent/JP5268144B2/ja not_active Expired - Fee Related
- 2006-03-16 US US11/816,217 patent/US8722764B2/en not_active Expired - Fee Related
- 2006-03-16 CA CA2599679A patent/CA2599679C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1858964A1 (en) | 2007-11-28 |
| US20080153975A1 (en) | 2008-06-26 |
| WO2006099630A1 (en) | 2006-09-21 |
| EP1858964B1 (en) | 2013-01-16 |
| CN101142263A (zh) | 2008-03-12 |
| JP2008533288A (ja) | 2008-08-21 |
| JP5268144B2 (ja) | 2013-08-21 |
| CA2599679A1 (en) | 2006-09-21 |
| US8722764B2 (en) | 2014-05-13 |
| CN101142263B (zh) | 2012-10-10 |
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| EEER | Examination request | ||
| MKLA | Lapsed |
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