CA2509699A1 - Electrically conductive polymerized macrocyclic oligomer carbon nanofiber compositions - Google Patents
Electrically conductive polymerized macrocyclic oligomer carbon nanofiber compositions Download PDFInfo
- Publication number
- CA2509699A1 CA2509699A1 CA002509699A CA2509699A CA2509699A1 CA 2509699 A1 CA2509699 A1 CA 2509699A1 CA 002509699 A CA002509699 A CA 002509699A CA 2509699 A CA2509699 A CA 2509699A CA 2509699 A1 CA2509699 A1 CA 2509699A1
- Authority
- CA
- Canada
- Prior art keywords
- polymer
- composition
- macrocyclic
- weight
- carbon nanotubes
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 89
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 title abstract description 29
- 239000002134 carbon nanofiber Substances 0.000 title abstract description 28
- 229920000642 polymer Polymers 0.000 claims abstract description 73
- 239000003054 catalyst Substances 0.000 claims description 26
- 125000000524 functional group Chemical group 0.000 claims description 25
- 238000006116 polymerization reaction Methods 0.000 claims description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- 229920001971 elastomer Polymers 0.000 claims description 18
- 239000005060 rubber Substances 0.000 claims description 18
- 239000011258 core-shell material Substances 0.000 claims description 17
- 239000011159 matrix material Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 239000002041 carbon nanotube Substances 0.000 claims description 9
- 229910021393 carbon nanotube Inorganic materials 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 229920000728 polyester Polymers 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 229920002601 oligoester Polymers 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 239000000835 fiber Substances 0.000 description 15
- -1 polyphenylene Polymers 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 12
- 125000002947 alkylene group Chemical group 0.000 description 10
- 239000002131 composite material Substances 0.000 description 10
- 229910002804 graphite Inorganic materials 0.000 description 8
- 239000010439 graphite Substances 0.000 description 8
- FQYHHEJETOLDHR-UHFFFAOYSA-K butyl(chloro)tin(2+);dihydroxide Chemical compound CCCC[Sn](O)(O)Cl FQYHHEJETOLDHR-UHFFFAOYSA-K 0.000 description 7
- 239000004020 conductor Substances 0.000 description 7
- 239000002071 nanotube Substances 0.000 description 7
- 229920001707 polybutylene terephthalate Polymers 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 6
- 238000005809 transesterification reaction Methods 0.000 description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 5
- 239000007822 coupling agent Substances 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 229910052718 tin Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229920001940 conductive polymer Polymers 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 238000006049 ring expansion reaction Methods 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 150000003606 tin compounds Chemical class 0.000 description 3
- 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 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000004917 carbon fiber Substances 0.000 description 2
- 125000002993 cycloalkylene group Chemical group 0.000 description 2
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- COKREYXJRHTKSH-UHFFFAOYSA-N 2,2-dibutyl-1,3,2-dioxastannepane Chemical compound CCCC[Sn]1(CCCC)OCCCCO1 COKREYXJRHTKSH-UHFFFAOYSA-N 0.000 description 1
- KTXWGMUMDPYXNN-UHFFFAOYSA-N 2-ethylhexan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-] KTXWGMUMDPYXNN-UHFFFAOYSA-N 0.000 description 1
- NMYFVWYGKGVPIW-UHFFFAOYSA-N 3,7-dioxabicyclo[7.2.2]trideca-1(11),9,12-triene-2,8-dione Chemical compound O=C1OCCCOC(=O)C2=CC=C1C=C2 NMYFVWYGKGVPIW-UHFFFAOYSA-N 0.000 description 1
- WSQZNZLOZXSBHA-UHFFFAOYSA-N 3,8-dioxabicyclo[8.2.2]tetradeca-1(12),10,13-triene-2,9-dione Chemical compound O=C1OCCCCOC(=O)C2=CC=C1C=C2 WSQZNZLOZXSBHA-UHFFFAOYSA-N 0.000 description 1
- LLLVZDVNHNWSDS-UHFFFAOYSA-N 4-methylidene-3,5-dioxabicyclo[5.2.2]undeca-1(9),7,10-triene-2,6-dione Chemical compound C1(C2=CC=C(C(=O)OC(=C)O1)C=C2)=O LLLVZDVNHNWSDS-UHFFFAOYSA-N 0.000 description 1
- PCXMISPZSFODLD-UHFFFAOYSA-N 6,9-dioxatricyclo[9.3.1.14,14]hexadeca-1(14),2,4(16),11(15),12-pentaene-5,10-dione Chemical compound C1=C(C=C2)C(=O)OCCOC(=O)C3=CC=C1C2=C3 PCXMISPZSFODLD-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000000071 blow moulding Methods 0.000 description 1
- RGCPMRIOBZXXBR-UHFFFAOYSA-N butan-1-olate;dibutyltin(2+) Chemical compound CCCCO[Sn](CCCC)(CCCC)OCCCC RGCPMRIOBZXXBR-UHFFFAOYSA-N 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000011231 conductive filler Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- LQRUPWUPINJLMU-UHFFFAOYSA-N dioctyl(oxo)tin Chemical compound CCCCCCCC[Sn](=O)CCCCCCCC LQRUPWUPINJLMU-UHFFFAOYSA-N 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 238000009503 electrostatic coating Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- XCRHYAQWBYDRGV-JXMROGBWSA-N ethyl (e)-3-(4-propan-2-ylphenyl)prop-2-enoate Chemical compound CCOC(=O)\C=C\C1=CC=C(C(C)C)C=C1 XCRHYAQWBYDRGV-JXMROGBWSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical class OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000002114 nanocomposite Substances 0.000 description 1
- 239000002121 nanofiber Substances 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical group C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- DTRIEULISHKBQO-UHFFFAOYSA-N tributoxy(butyl)stannane Chemical compound CCCCO[Sn](CCCC)(OCCCC)OCCCC DTRIEULISHKBQO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08K7/00—Use of ingredients characterised by shape
- C08K7/02—Fibres or whiskers
- C08K7/04—Fibres or whiskers inorganic
- C08K7/06—Elements
-
- 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
- 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
- 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
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
-
- 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
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J5/0405—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres
- C08J5/042—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres with carbon fibres
-
- 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
- C08K7/00—Use of ingredients characterised by shape
- C08K7/22—Expanded, porous or hollow particles
- C08K7/24—Expanded, porous or hollow particles inorganic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/04—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to rubbers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/34—Oligomeric, e.g. cyclic oligomeric
-
- 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
- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- 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
- C08K2201/00—Specific properties of additives
- C08K2201/011—Nanostructured additives
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Nanotechnology (AREA)
- Manufacturing & Machinery (AREA)
- Physics & Mathematics (AREA)
- Composite Materials (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
- Conductive Materials (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43640002P | 2002-12-23 | 2002-12-23 | |
| US60/436,400 | 2002-12-23 | ||
| PCT/US2003/040722 WO2004058872A1 (en) | 2002-12-23 | 2003-12-19 | Electrically conductive polymerized macrocyclic oligomer carbon nanofiber compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2509699A1 true CA2509699A1 (en) | 2004-07-15 |
Family
ID=32682385
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002509699A Abandoned CA2509699A1 (en) | 2002-12-23 | 2003-12-19 | Electrically conductive polymerized macrocyclic oligomer carbon nanofiber compositions |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20060148963A1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1578857A1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2006511652A (cg-RX-API-DMAC7.html) |
| KR (1) | KR20050096099A (cg-RX-API-DMAC7.html) |
| CN (1) | CN1732217A (cg-RX-API-DMAC7.html) |
| AU (1) | AU2003301178A1 (cg-RX-API-DMAC7.html) |
| BR (1) | BR0317205A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2509699A1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2004058872A1 (cg-RX-API-DMAC7.html) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9663640B2 (en) | 2013-12-19 | 2017-05-30 | Soucy Techno Inc. | Rubber compositions and uses thereof |
| US9840611B2 (en) | 2013-10-18 | 2017-12-12 | Soucy Techno Inc. | Rubber compositions and uses thereof |
| US9849651B2 (en) | 2010-02-15 | 2017-12-26 | Productive Research Llc | Formable light weight composite material systems and methods |
| US9879131B2 (en) | 2012-08-31 | 2018-01-30 | Soucy Techno Inc. | Rubber compositions and uses thereof |
| US9889634B2 (en) | 2008-08-18 | 2018-02-13 | Productive Research Llc | Formable light weight composites |
| US11338552B2 (en) | 2019-02-15 | 2022-05-24 | Productive Research Llc | Composite materials, vehicle applications and methods thereof |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6960626B2 (en) | 2000-01-21 | 2005-11-01 | Cyclics Corporation | Intimate physical mixtures containing macrocyclic polyester oligomer and filler |
| US7256241B2 (en) | 2000-01-21 | 2007-08-14 | Cyclics Corporation | Methods for polymerizing macrocyclic polyester oligomers using catalyst promoters |
| US6906147B2 (en) | 2002-03-20 | 2005-06-14 | Cyclics Corporation | Catalytic systems |
| US7151143B2 (en) | 2000-01-21 | 2006-12-19 | Cyclics Corporation | Blends containing macrocyclic polyester oligomer and high molecular weight polymer |
| AU2001288663A1 (en) | 2000-09-01 | 2002-03-13 | Cyclics Corporation | Methods for converting linear polyesters to macrocyclic oligoester compositions and macrocyclic oligoesters |
| US7750109B2 (en) | 2000-09-01 | 2010-07-06 | Cyclics Corporation | Use of a residual oligomer recyclate in the production of macrocyclic polyester oligomer |
| US7767781B2 (en) | 2000-09-01 | 2010-08-03 | Cyclics Corporation | Preparation of low-acid polyalkylene terephthalate and preparation of macrocyclic polyester oligomer therefrom |
| DE60226789D1 (de) | 2001-06-27 | 2008-07-03 | Cyclics Corp | Formgebende Verarbeitung von makrozyklischen Oligoestern |
| US7304123B2 (en) | 2001-06-27 | 2007-12-04 | Cyclics Corporation | Processes for shaping macrocyclic oligoesters |
| US6787632B2 (en) | 2001-10-09 | 2004-09-07 | Cyclics Corporation | Organo-titanate catalysts for preparing pure macrocyclic oligoesters |
| US20080007890A1 (en) * | 2004-09-30 | 2008-01-10 | Harmon Julianne P | Thermally conductive composite and uses for microelectronic packaging |
| EP1794224A1 (en) * | 2004-09-30 | 2007-06-13 | Honeywell International Inc. | Thermally conductive composite and uses for microelectronic packaging |
| WO2008060675A2 (en) * | 2006-06-01 | 2008-05-22 | Invista Technologies S.A R.L. | Coaxial polycarbonate/polyurethane composite nanofibers |
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- 2003-12-19 EP EP03814248A patent/EP1578857A1/en not_active Withdrawn
- 2003-12-19 WO PCT/US2003/040722 patent/WO2004058872A1/en not_active Ceased
- 2003-12-19 BR BR0317205-8A patent/BR0317205A/pt not_active Application Discontinuation
- 2003-12-19 CA CA002509699A patent/CA2509699A1/en not_active Abandoned
- 2003-12-19 KR KR1020057011721A patent/KR20050096099A/ko not_active Withdrawn
- 2003-12-19 CN CNA2003801073368A patent/CN1732217A/zh active Pending
- 2003-12-19 JP JP2004563861A patent/JP2006511652A/ja active Pending
- 2003-12-19 AU AU2003301178A patent/AU2003301178A1/en not_active Abandoned
- 2003-12-19 US US10/541,103 patent/US20060148963A1/en not_active Abandoned
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US9889634B2 (en) | 2008-08-18 | 2018-02-13 | Productive Research Llc | Formable light weight composites |
| US9849651B2 (en) | 2010-02-15 | 2017-12-26 | Productive Research Llc | Formable light weight composite material systems and methods |
| US9981451B2 (en) | 2010-02-15 | 2018-05-29 | Productive Research Llc | Delamination resistant, weldable and formable light weight composites |
| US10457019B2 (en) | 2010-02-15 | 2019-10-29 | Productive Research Llc | Light weight composite material systems, polymeric materials, and methods |
| US10710338B2 (en) | 2010-02-15 | 2020-07-14 | Productive Research Llc | Delamination resistant, weldable and formable light weight composites |
| US11084253B2 (en) | 2010-02-15 | 2021-08-10 | Productive Research Llc | Light weight composite material systems, polymeric materials, and methods |
| US11331880B2 (en) | 2010-02-15 | 2022-05-17 | Productive Research Llc | Delamination resistant, weldable and formable light weight composites |
| US9879131B2 (en) | 2012-08-31 | 2018-01-30 | Soucy Techno Inc. | Rubber compositions and uses thereof |
| US9840611B2 (en) | 2013-10-18 | 2017-12-12 | Soucy Techno Inc. | Rubber compositions and uses thereof |
| US9663640B2 (en) | 2013-12-19 | 2017-05-30 | Soucy Techno Inc. | Rubber compositions and uses thereof |
| US11338552B2 (en) | 2019-02-15 | 2022-05-24 | Productive Research Llc | Composite materials, vehicle applications and methods thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003301178A1 (en) | 2004-07-22 |
| EP1578857A1 (en) | 2005-09-28 |
| US20060148963A1 (en) | 2006-07-06 |
| WO2004058872A1 (en) | 2004-07-15 |
| KR20050096099A (ko) | 2005-10-05 |
| BR0317205A (pt) | 2005-11-01 |
| JP2006511652A (ja) | 2006-04-06 |
| CN1732217A (zh) | 2006-02-08 |
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