TWI317741B - Nanoscale polymerized hydrocarbon particles and methods of making and using such particles - Google Patents
Nanoscale polymerized hydrocarbon particles and methods of making and using such particles Download PDFInfo
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- TWI317741B TWI317741B TW092103133A TW92103133A TWI317741B TW I317741 B TWI317741 B TW I317741B TW 092103133 A TW092103133 A TW 092103133A TW 92103133 A TW92103133 A TW 92103133A TW I317741 B TWI317741 B TW I317741B
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- 239000002245 particle Substances 0.000 title claims description 104
- 238000000034 method Methods 0.000 title claims description 51
- 239000004215 Carbon black (E152) Substances 0.000 title claims description 14
- 229930195733 hydrocarbon Natural products 0.000 title claims description 14
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 14
- 239000000203 mixture Substances 0.000 claims description 63
- 239000000178 monomer Substances 0.000 claims description 61
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 238000006116 polymerization reaction Methods 0.000 claims description 35
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 34
- 239000002904 solvent Substances 0.000 claims description 30
- 239000004094 surface-active agent Substances 0.000 claims description 23
- 229910001868 water Inorganic materials 0.000 claims description 21
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 19
- 239000000839 emulsion Substances 0.000 claims description 19
- 239000007858 starting material Substances 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 229920000642 polymer Polymers 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 235000010323 ascorbic acid Nutrition 0.000 claims description 17
- 239000011668 ascorbic acid Substances 0.000 claims description 17
- 239000003999 initiator Substances 0.000 claims description 17
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- 229960005070 ascorbic acid Drugs 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 239000008346 aqueous phase Substances 0.000 claims description 13
- -1 polyoxyethylene Polymers 0.000 claims description 12
- 229920002223 polystyrene Polymers 0.000 claims description 12
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
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- 229910021645 metal ion Inorganic materials 0.000 claims description 11
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- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 239000002563 ionic surfactant Substances 0.000 claims description 9
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 9
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- 238000010586 diagram Methods 0.000 claims description 6
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 5
- 238000007792 addition Methods 0.000 claims description 5
- 238000010526 radical polymerization reaction Methods 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
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- 150000002148 esters Chemical class 0.000 claims description 4
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- 238000005979 thermal decomposition reaction Methods 0.000 claims description 3
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- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000000217 alkyl group Polymers 0.000 claims description 2
- 150000001993 dienes Chemical class 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 239000000052 vinegar Substances 0.000 claims description 2
- 235000021419 vinegar Nutrition 0.000 claims description 2
- 239000011159 matrix material Substances 0.000 claims 5
- 239000002243 precursor Substances 0.000 claims 5
- 239000000194 fatty acid Substances 0.000 claims 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims 2
- 229930195729 fatty acid Natural products 0.000 claims 2
- 150000004665 fatty acids Chemical class 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
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- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- 229940072107 ascorbate Drugs 0.000 claims 1
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 claims 1
- 239000008199 coating composition Substances 0.000 claims 1
- 238000011109 contamination Methods 0.000 claims 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims 1
- 125000005456 glyceride group Chemical group 0.000 claims 1
- 150000002334 glycols Chemical class 0.000 claims 1
- 239000002923 metal particle Substances 0.000 claims 1
- 235000013336 milk Nutrition 0.000 claims 1
- 239000008267 milk Substances 0.000 claims 1
- 210000004080 milk Anatomy 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- 229920000223 polyglycerol Polymers 0.000 claims 1
- 229920001451 polypropylene glycol Polymers 0.000 claims 1
- 150000003333 secondary alcohols Chemical class 0.000 claims 1
- 239000000600 sorbitol Substances 0.000 claims 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 13
- 238000009826 distribution Methods 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- 230000008569 process Effects 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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- 238000000926 separation method Methods 0.000 description 4
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- IBVPVTPPYGGAEL-UHFFFAOYSA-N 1,3-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC(C(C)=C)=C1 IBVPVTPPYGGAEL-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- 229910052802 copper Inorganic materials 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 239000004064 cosurfactant Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- UURSXESKOOOTOV-UHFFFAOYSA-N dec-5-ene Chemical compound CCCCC=CCCCC UURSXESKOOOTOV-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- GTBGXKPAKVYEKJ-UHFFFAOYSA-N decyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C(C)=C GTBGXKPAKVYEKJ-UHFFFAOYSA-N 0.000 description 1
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000000635 electron micrograph Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 238000009616 inductively coupled plasma Methods 0.000 description 1
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 210000002445 nipple Anatomy 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- VSZWPYCFIRKVQL-UHFFFAOYSA-N selanylidenegallium;selenium Chemical compound [Se].[Se]=[Ga].[Se]=[Ga] VSZWPYCFIRKVQL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- BGKZULDOBMANRY-UHFFFAOYSA-N sulfanyl prop-2-enoate Chemical compound SOC(=O)C=C BGKZULDOBMANRY-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000008096 xylene Substances 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
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
- C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
-
- 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
- C08F2/22—Emulsion polymerisation
- C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
- C08F2/30—Emulsion polymerisation with the aid of emulsifying agents non-ionic
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82B—NANOSTRUCTURES FORMED BY MANIPULATION OF INDIVIDUAL ATOMS, MOLECULES, OR LIMITED COLLECTIONS OF ATOMS OR MOLECULES AS DISCRETE UNITS; MANUFACTURE OR TREATMENT THEREOF
- B82B3/00—Manufacture or treatment of nanostructures by manipulation of individual atoms or molecules, or limited collections of atoms or molecules as discrete units
-
- 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
- C08J3/12—Powdering or granulating
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Nanotechnology (AREA)
- Manufacturing & Machinery (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/077,642 US20030162890A1 (en) | 2002-02-15 | 2002-02-15 | Nanoscale polymerized hydrocarbon particles and methods of making and using such particles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200400201A TW200400201A (en) | 2004-01-01 |
| TWI317741B true TWI317741B (en) | 2009-12-01 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW092103133A TWI317741B (en) | 2002-02-15 | 2003-02-14 | Nanoscale polymerized hydrocarbon particles and methods of making and using such particles |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US20030162890A1 (enExample) |
| EP (1) | EP1478669A1 (enExample) |
| JP (2) | JP4237634B2 (enExample) |
| KR (1) | KR20040082432A (enExample) |
| CN (1) | CN100595215C (enExample) |
| AU (1) | AU2003217536A1 (enExample) |
| TW (1) | TWI317741B (enExample) |
| WO (1) | WO2003070777A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US6946382B2 (en) | 2002-04-02 | 2005-09-20 | Dow Global Technologies Inc. | Process for making air gap containing semiconducting devices and resulting semiconducting device |
| US7244784B2 (en) * | 2002-06-14 | 2007-07-17 | Rohm And Haas Company | Aqueous nanoparticle dispersions |
| AU2003204606A1 (en) * | 2002-06-14 | 2004-01-15 | Rohm And Haas Company | Water-based adhesives |
| US8272872B2 (en) * | 2002-06-27 | 2012-09-25 | National Wrestling Coaches Association | System and method for calculating optimal performance and weight classification |
| US7138438B2 (en) | 2002-09-30 | 2006-11-21 | Rohm And Haas Company | Polymeric nanoparticle formulations and their use for improving the dirt pick up resistance of a coating |
| US7244775B2 (en) * | 2002-09-30 | 2007-07-17 | Rohm And Haas Company | Damage resistant coatings, films and articles of manufacture containing crosslinked nanoparticles |
| EP1411076A1 (en) * | 2002-10-15 | 2004-04-21 | Rohm And Haas Company | Continuous production of crosslinked polymer nanoparticles |
| US6972148B2 (en) * | 2003-06-23 | 2005-12-06 | Kimberly-Clark Worldwide, Inc. | Glove having improved donning characteristics |
| JP2007505976A (ja) * | 2003-09-19 | 2007-03-15 | ダウ グローバル テクノロジーズ インコーポレイティド | 結合ポラゲン含有多官能性モノマー及びそれからのポリアリーレン組成物 |
| JP2007515501A (ja) * | 2003-09-19 | 2007-06-14 | ダウ グローバル テクノロジーズ インコーポレイティド | 多官能性モノマー及びそれからのポリアリーレン組成物 |
| JP4885724B2 (ja) | 2003-10-21 | 2012-02-29 | ダウ グローバル テクノロジーズ エルエルシー | 結合メソゲン性ポラゲン形成性部分を含有する多官能性モノマー及びそれからのポリアリーレン組成物 |
| WO2005037761A2 (en) | 2003-10-21 | 2005-04-28 | Dow Global Technologies Inc. | Multifunctional ethynyl substituted monomers and polyarylene compositions therefrom |
| JP5097506B2 (ja) | 2007-11-05 | 2012-12-12 | 日東電工株式会社 | 水酸基を有する多孔質樹脂粒子の製造方法 |
| EP2231760A1 (en) * | 2007-12-28 | 2010-09-29 | Dow Global Technologies Inc. | Small scale functional materials |
| CN101960364A (zh) * | 2007-12-28 | 2011-01-26 | 陶氏环球技术公司 | 包含吸收有液晶物质的聚合物纳米粒子的相位补偿膜 |
| US8592040B2 (en) | 2008-09-05 | 2013-11-26 | Basf Se | Polymer emulsion coating or binding formulations and methods of making and using same |
| US9017520B2 (en) | 2010-03-23 | 2015-04-28 | Basf Se | Paper coating or binding formulations and methods of making and using same |
| US9102848B2 (en) | 2011-02-28 | 2015-08-11 | Basf Se | Environmentally friendly, polymer dispersion-based coating formulations and methods of preparing and using same |
| EP3121217B1 (en) * | 2014-03-20 | 2019-07-17 | Mitsubishi Chemical Corporation | Vinyl polymer powder, thermoplastic resin composition, and molded body thereof |
| JP6981870B2 (ja) * | 2017-12-25 | 2021-12-17 | Ｔｏｙｏ Ｔｉｒｅ株式会社 | ポリマー粒子の製造方法 |
| EP4015541A1 (en) | 2020-12-15 | 2022-06-22 | Clariant International Ltd | Miniemulsions comprising superhydrophobic and/or hydrophobic monomers, method of preparing the same and use thereof |
| JP2023145009A (ja) * | 2022-03-28 | 2023-10-11 | 旭化成株式会社 | 多官能ビニル芳香族共重合体 |
| CN122043417B (zh) * | 2026-04-15 | 2026-08-04 | 浙江禾秒科技有限公司 | 激光雷达及分光棱镜 |
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| US10294A (en) * | 1853-12-06 | Penholdeb | ||
| DE3012821A1 (de) * | 1980-04-02 | 1981-10-08 | Bayer Ag, 5090 Leverkusen | Waessrige kunststoffdispersionen mit einem mittleren durchmesser der dispersionsteilchen im bereich von etwa 50 bis 500 nm und ein verfahren zu ihrer herstellung |
| FR2564848B1 (fr) * | 1984-05-25 | 1989-04-28 | Nippon Paint Co Ltd | Composition pour couche de finition contenant des particules de microgel. |
| US4653372A (en) * | 1985-06-26 | 1987-03-31 | Pottorff Earl T | Self-sharpening hole punch for plastic bags |
| JPH0786122B2 (ja) * | 1986-05-30 | 1995-09-20 | 日本ペイント株式会社 | 三次元架橋された微小樹脂粒子およびその製造法 |
| CH681950A5 (enExample) * | 1989-06-08 | 1993-06-30 | Superba Sa | |
| DE3922784A1 (de) * | 1989-07-11 | 1991-01-17 | Synthomer Chemie Gmbh | Verfahren zur herstellung waessriger, dextrinhaltiger polymerisatdispersionen |
| CA2032695A1 (en) * | 1989-12-20 | 1991-06-21 | Hiroshi Akimoto | Condensed heterocyclic compounds, their production and use |
| JPH0822983B2 (ja) * | 1990-02-27 | 1996-03-06 | 日本ペイント株式会社 | 架橋微小樹脂粒子とその用途 |
| US5212273A (en) * | 1991-06-20 | 1993-05-18 | Ppg Industries, Inc. | Crosslinked polymeric microparticles; their method of preparation and use in coating compositions |
| DE69213760T2 (de) * | 1991-12-17 | 1997-04-10 | Minnesota Mining & Mfg | Haftfreie elastomere acrylat-mikrokugeln |
| DE4213965A1 (de) * | 1992-04-29 | 1993-11-04 | Basf Ag | Waessrige polymerisatdispersion |
| DE4213969A1 (de) * | 1992-04-29 | 1993-11-04 | Basf Ag | Waessrige polymerisatdispersion |
| DE4213967A1 (de) * | 1992-04-29 | 1993-11-04 | Basf Ag | Waessrige polymerisatdispersion |
| US5298833A (en) * | 1992-06-22 | 1994-03-29 | Copytele, Inc. | Black electrophoretic particles for an electrophoretic image display |
| US5504170A (en) * | 1993-08-27 | 1996-04-02 | W. L. Gore & Associates, Inc. | Aqueous microemulsion polymerization of tetrafluoroethylene |
| US5484840A (en) * | 1993-12-21 | 1996-01-16 | Binkley; Jesse A. | Textile sizes containing ultrafine-sized aqueous polymeric dispersions |
| JPH07228611A (ja) * | 1994-02-15 | 1995-08-29 | Japan Synthetic Rubber Co Ltd | ポリマーエマルジョン |
| US5523346A (en) * | 1994-06-10 | 1996-06-04 | W. L. Gore & Associates, Inc. | Seeded microemulsion polymerization for the production of small polymer particles |
| DE4443887A1 (de) * | 1994-12-09 | 1996-06-13 | Basf Ag | Wäßrige Polymeridispersionen |
| US5895799A (en) * | 1995-01-18 | 1999-04-20 | W. L. Gore & Associates, Inc. | Microemulsion polymerization process for the production of small polytetrafluoroethylene polymer particles |
| US6046271A (en) * | 1995-01-18 | 2000-04-04 | W. L. Gore & Associates, Inc. | Microemulsion polymerization systems for the production of small melt-processible fluoropolymer particles |
| WO1996022313A1 (en) * | 1995-01-18 | 1996-07-25 | W.L. Gore & Associates, Inc. | Microemulsion polymerization systems for tetrafluoroethylene |
| US5580654A (en) * | 1995-02-22 | 1996-12-03 | W. L. Gore & Associates, Inc. | Insulated electrical conductor |
| US5539021A (en) * | 1995-06-05 | 1996-07-23 | The Dow Chemical Company | Process for preparing high internal phase ratio emulsions and latexes derived thereof |
| US5756573A (en) * | 1995-10-05 | 1998-05-26 | Sc Johnson Commerical Markets, Inc. | Seed polymerized latex polymer having a gradient polymeric morphology and process for preparing the same |
| US5889104A (en) * | 1996-01-11 | 1999-03-30 | W. L. Gore & Associates, Inc. | Low dielectric constant material for use as an insulation element in an electronic device |
| US5700844A (en) * | 1996-04-09 | 1997-12-23 | International Business Machines Corporation | Process for making a foamed polymer |
| DE19624280A1 (de) * | 1996-06-18 | 1998-01-02 | Basf Ag | Verfahren zur Herstellung niedrigviskoser, wässriger Polymerisatdispersionen mit Polymervolumenkonzentrationen von wenigstens 50 Vol.-% |
| US5965679A (en) * | 1996-09-10 | 1999-10-12 | The Dow Chemical Company | Polyphenylene oligomers and polymers |
| JP3568349B2 (ja) * | 1997-03-11 | 2004-09-22 | ライオン株式会社 | 水硬性無機材料用混和剤及び水硬性無機材料用プライマー |
| JPH1121305A (ja) * | 1997-06-30 | 1999-01-26 | Toagosei Co Ltd | 硬化性エマルジョンの製造方法 |
| US6197878B1 (en) * | 1997-08-28 | 2001-03-06 | Eastman Chemical Company | Diol latex compositions and modified condensation polymers |
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| JP2000038492A (ja) * | 1998-07-24 | 2000-02-08 | Asahi Chem Ind Co Ltd | 分散染料可染用のラテックス |
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| US20020072580A1 (en) * | 2000-01-26 | 2002-06-13 | Aert Huub Van | Method of emulsion polymerization |
| US6391932B1 (en) * | 2000-08-08 | 2002-05-21 | Shipley Company, L.L.C. | Porous materials |
| AU2001286651A1 (en) * | 2000-08-22 | 2002-03-04 | Purdue Research Foundation | Microparticle composition and method |
| DE60013154T2 (de) * | 2000-12-20 | 2005-09-08 | Agfa-Gevaert | Verfahren zur Emulsionspolymerisation |
| US6903175B2 (en) * | 2001-03-26 | 2005-06-07 | Shipley Company, L.L.C. | Polymer synthesis and films therefrom |
| US6787601B2 (en) * | 2001-03-26 | 2004-09-07 | Shipley Company, L.L.C. | Polymer synthesis |
| US6881805B2 (en) * | 2002-01-11 | 2005-04-19 | National Starch And Chemical Investment Holding Corporation | Free radical retrograde precipitation polymer dispersions |
-
2002
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2003
- 2003-02-12 AU AU2003217536A patent/AU2003217536A1/en not_active Abandoned
- 2003-02-12 EP EP03713487A patent/EP1478669A1/en not_active Withdrawn
- 2003-02-12 JP JP2003569684A patent/JP4237634B2/ja not_active Expired - Fee Related
- 2003-02-12 KR KR10-2004-7012640A patent/KR20040082432A/ko not_active Ceased
- 2003-02-12 CN CN03808317A patent/CN100595215C/zh not_active Expired - Fee Related
- 2003-02-12 WO PCT/US2003/004668 patent/WO2003070777A1/en not_active Ceased
- 2003-02-14 TW TW092103133A patent/TWI317741B/zh not_active IP Right Cessation
- 2003-07-15 US US10/366,494 patent/US20040054111A1/en not_active Abandoned
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2008
- 2008-10-24 JP JP2008274544A patent/JP2009041038A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN100595215C (zh) | 2010-03-24 |
| WO2003070777A1 (en) | 2003-08-28 |
| EP1478669A1 (en) | 2004-11-24 |
| TW200400201A (en) | 2004-01-01 |
| JP2009041038A (ja) | 2009-02-26 |
| JP4237634B2 (ja) | 2009-03-11 |
| US20040054111A1 (en) | 2004-03-18 |
| US20030162890A1 (en) | 2003-08-28 |
| CN1646570A (zh) | 2005-07-27 |
| JP2005517772A (ja) | 2005-06-16 |
| KR20040082432A (ko) | 2004-09-24 |
| AU2003217536A1 (en) | 2003-09-09 |
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