JP6628814B2 - ポリイミド前駆体の材料押出し付加製造 - Google Patents
ポリイミド前駆体の材料押出し付加製造 Download PDFInfo
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- JP6628814B2 JP6628814B2 JP2017562687A JP2017562687A JP6628814B2 JP 6628814 B2 JP6628814 B2 JP 6628814B2 JP 2017562687 A JP2017562687 A JP 2017562687A JP 2017562687 A JP2017562687 A JP 2017562687A JP 6628814 B2 JP6628814 B2 JP 6628814B2
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- Prior art keywords
- precursor solution
- polyimide
- compound
- precursor
- beads
- Prior art date
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- 239000002243 precursor Substances 0.000 title claims description 579
- 239000004642 Polyimide Substances 0.000 title claims description 382
- 229920001721 polyimide Polymers 0.000 title claims description 382
- 238000001125 extrusion Methods 0.000 title claims description 204
- 238000004519 manufacturing process Methods 0.000 title claims description 18
- 239000000654 additive Substances 0.000 title description 15
- 230000000996 additive effect Effects 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims description 274
- 239000011324 bead Substances 0.000 claims description 172
- 150000004985 diamines Chemical class 0.000 claims description 100
- 239000002904 solvent Substances 0.000 claims description 91
- 238000000034 method Methods 0.000 claims description 90
- 238000010438 heat treatment Methods 0.000 claims description 70
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 53
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 50
- 238000006116 polymerization reaction Methods 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 40
- 239000000758 substrate Substances 0.000 claims description 34
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 23
- 238000002156 mixing Methods 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 150000003512 tertiary amines Chemical class 0.000 claims description 17
- 150000003335 secondary amines Chemical class 0.000 claims description 16
- 239000007795 chemical reaction product Substances 0.000 claims description 13
- 230000007613 environmental effect Effects 0.000 claims description 12
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- 238000005755 formation reaction Methods 0.000 claims description 6
- 229940126062 Compound A Drugs 0.000 claims 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 2
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- -1 for example Substances 0.000 description 33
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- 150000001412 amines Chemical class 0.000 description 21
- 150000008064 anhydrides Chemical class 0.000 description 18
- 239000012530 fluid Substances 0.000 description 13
- 125000003118 aryl group Chemical group 0.000 description 11
- 239000000945 filler Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 238000004090 dissolution Methods 0.000 description 10
- 229920001601 polyetherimide Polymers 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- 238000009792 diffusion process Methods 0.000 description 8
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- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 8
- 239000004697 Polyetherimide Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 6
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 6
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- 230000015572 biosynthetic process Effects 0.000 description 5
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 5
- 229960002887 deanol Drugs 0.000 description 5
- 239000012972 dimethylethanolamine Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 description 5
- 125000001174 sulfone group Chemical group 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000004971 Cross linker Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 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
- 238000009835 boiling Methods 0.000 description 4
- 239000006085 branching agent Substances 0.000 description 4
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- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 238000009736 wetting Methods 0.000 description 4
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
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- 238000000576 coating method Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 229940117389 dichlorobenzene Drugs 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
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- 229920000578 graft copolymer Polymers 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 150000003949 imides Chemical group 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- 239000004611 light stabiliser Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000006551 perfluoro alkylene group Chemical group 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000011800 void material Substances 0.000 description 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- 125000006755 (C2-C20) alkyl group Chemical group 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
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- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
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- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
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- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
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- 239000011261 inert gas Substances 0.000 description 2
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
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- 239000002356 single layer Substances 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
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- QPIOXOJERGNNMX-UHFFFAOYSA-N 3-(3-aminopropylsulfanyl)propan-1-amine Chemical compound NCCCSCCCN QPIOXOJERGNNMX-UHFFFAOYSA-N 0.000 description 1
- POTQBGGWSWSMCX-UHFFFAOYSA-N 3-[2-(3-aminopropoxy)ethoxy]propan-1-amine Chemical compound NCCCOCCOCCCN POTQBGGWSWSMCX-UHFFFAOYSA-N 0.000 description 1
- XZWYIEAOALEANP-UHFFFAOYSA-N 3-[4-[2-[4-(2,3-dicarboxyphenoxy)phenyl]propan-2-yl]phenoxy]phthalic acid Chemical compound C=1C=C(OC=2C(=C(C(O)=O)C=CC=2)C(O)=O)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=CC(C(O)=O)=C1C(O)=O XZWYIEAOALEANP-UHFFFAOYSA-N 0.000 description 1
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Images
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- B29C64/00—Additive manufacturing, i.e. manufacturing of three-dimensional [3D] objects by additive deposition, additive agglomeration or additive layering, e.g. by 3D printing, stereolithography or selective laser sintering
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- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
- C08G73/1028—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous
- C08G73/1032—Preparatory processes from tetracarboxylic acids or derivatives and diamines characterised by the process itself, e.g. steps, continuous characterised by the solvent(s) used
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- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
- C08G73/1053—Polyimides containing oxygen in the form of ether bonds in the main chain with oxygen only in the tetracarboxylic moiety
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
- C08G73/106—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing silicon
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1057—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain
- C08G73/1064—Polyimides containing other atoms than carbon, hydrogen, nitrogen or oxygen in the main chain containing sulfur
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
- C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29K—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR MOULDS, REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- B29K2079/00—Use of polymers having nitrogen, with or without oxygen or carbon only, in the main chain, not provided for in groups B29K2061/00 - B29K2077/00, as moulding material
- B29K2079/08—PI, i.e. polyimides or derivatives thereof
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
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- Manufacturing & Machinery (AREA)
- Optics & Photonics (AREA)
- Mechanical Engineering (AREA)
- Physics & Mathematics (AREA)
- Ceramic Engineering (AREA)
- Civil Engineering (AREA)
- Composite Materials (AREA)
- Structural Engineering (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
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| US201562170423P | 2015-06-03 | 2015-06-03 | |
| US62/170,423 | 2015-06-03 | ||
| PCT/IB2016/053246 WO2016193933A1 (en) | 2015-06-03 | 2016-06-02 | Material extrusion additive manufacturing of polyimide precursor |
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| JP2018519186A JP2018519186A (ja) | 2018-07-19 |
| JP2018519186A5 JP2018519186A5 (enExample) | 2019-07-04 |
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| CN (1) | CN107848197A (enExample) |
| WO (1) | WO2016193933A1 (enExample) |
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| CN106068177B (zh) * | 2014-03-06 | 2017-12-19 | 沙特基础工业全球技术有限公司 | 增材制造的具有阻燃性的制品、制成方法及测试它们的阻燃性的方法 |
| JP6685200B2 (ja) * | 2016-08-09 | 2020-04-22 | 株式会社ミマキエンジニアリング | 三次元造形装置 |
| WO2018158426A1 (en) * | 2017-03-02 | 2018-09-07 | Bond High Performance 3D Technology B.V. | Object made by additive manufacturing and method to produce said object |
| EP3732023B1 (en) * | 2017-12-28 | 2024-06-26 | Stratasys Ltd. | Additive manufacturing employing polyimide-containing formulations |
| WO2019130312A2 (en) * | 2017-12-28 | 2019-07-04 | Stratasys Ltd. | Additive manufacturing employing solvent-free polyimide-containing formulations |
| KR102056948B1 (ko) | 2018-02-05 | 2019-12-17 | 주식회사 빌릭스 | 빌리루빈 유도체 기반의 진단 및 치료용 초음파 조영제 |
| JP7249803B2 (ja) * | 2018-03-30 | 2023-03-31 | 株式会社カネカ | 重合体製造システム及び製造方法 |
| JP7249802B2 (ja) * | 2018-03-30 | 2023-03-31 | 株式会社カネカ | 重合体製造システム及び製造方法 |
| JP7249801B2 (ja) * | 2018-03-30 | 2023-03-31 | 株式会社カネカ | ポリアミック酸製造システム及び製造方法、並びにポリイミド製造システム及び製造方法 |
| CN110408202B (zh) * | 2018-04-27 | 2020-10-27 | 中国科学院化学研究所 | 一种用于熔融沉积成形的热固性组合物及其制备得到的制品和制法 |
| JP7349239B2 (ja) * | 2018-10-03 | 2023-09-22 | 株式会社カネカ | 重合体製造システム及び重合体の製造方法 |
| JP7336302B2 (ja) * | 2019-07-31 | 2023-08-31 | 株式会社カネカ | 重合体製造システム及び製造方法 |
| EP4031352A4 (en) * | 2019-09-18 | 2023-10-11 | Triex, LLC | SYSTEM AND METHOD FOR GENERATIVE MANUFACTURING |
| GB2606780A (en) * | 2021-09-27 | 2022-11-23 | E3D Online Ltd | Nozzle |
| US12403653B2 (en) | 2023-04-21 | 2025-09-02 | Dyze Design | Extruder head assembly for additive manufacturing machines |
| US20250084265A1 (en) * | 2023-09-13 | 2025-03-13 | Lawrence Livermore National Security, Llc | Direct ink write additive manufacturing of thermoplastic polymers and thermoplastic polymer composites at ambient conditions |
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| DE3301197A1 (de) * | 1983-01-15 | 1984-07-19 | Akzo Gmbh, 5600 Wuppertal | Polyimid-laminate mit hoher schaelfestigkeit |
| TW252125B (enExample) * | 1991-08-28 | 1995-07-21 | Yunichica Kk | |
| JP3021979B2 (ja) * | 1991-08-28 | 2000-03-15 | ユニチカ株式会社 | ポリイミド前駆体溶液、その製造方法、それから得られる成形体及び被覆物 |
| US6322728B1 (en) * | 1998-07-10 | 2001-11-27 | Jeneric/Pentron, Inc. | Mass production of dental restorations by solid free-form fabrication methods |
| US7314591B2 (en) * | 2001-05-11 | 2008-01-01 | Stratasys, Inc. | Method for three-dimensional modeling |
| US20020113331A1 (en) * | 2000-12-20 | 2002-08-22 | Tan Zhang | Freeform fabrication method using extrusion of non-cross-linking reactive prepolymers |
| JP4132825B2 (ja) * | 2002-01-10 | 2008-08-13 | 日東電工株式会社 | 金属箔積層体及びその製造方法 |
| US7625200B2 (en) * | 2007-07-31 | 2009-12-01 | Stratasys, Inc. | Extrusion head for use in extrusion-based layered deposition modeling |
| US9527242B2 (en) * | 2012-11-21 | 2016-12-27 | Stratasys, Inc. | Method for printing three-dimensional parts wtih crystallization kinetics control |
| US9744722B2 (en) * | 2012-11-21 | 2017-08-29 | Stratasys, Inc. | Additive manufacturing with polyamide consumable materials |
| US9592530B2 (en) * | 2012-11-21 | 2017-03-14 | Stratasys, Inc. | Additive manufacturing with polyamide consumable materials |
| JP5846136B2 (ja) * | 2013-01-31 | 2016-01-20 | 富士ゼロックス株式会社 | ポリイミド前駆体組成物、及びポリイミド前駆体組成物の製造方法 |
| CN107813495A (zh) * | 2013-03-22 | 2018-03-20 | 格雷戈里·托马斯·马克 | 三维打印 |
| US20160167299A1 (en) * | 2013-07-31 | 2016-06-16 | Essilor International(Compagnie Generale D'optique) | Additive manufacturing for transparent ophthalmic lens |
| CN103980489B (zh) * | 2014-04-30 | 2018-08-31 | 中国科学院化学研究所 | 一种低熔体黏度热塑性聚酰亚胺材料及其3d打印成型方法 |
| CN104407409B (zh) * | 2014-05-31 | 2017-01-11 | 福州大学 | 一种动态液晶光栅的3d打印方法 |
| CN105313332B (zh) * | 2014-06-09 | 2020-05-05 | 联合工艺公司 | 由两部分组成的热固性树脂增材制造系统 |
| CN104228067A (zh) * | 2014-07-23 | 2014-12-24 | 中国科学院重庆绿色智能技术研究院 | 一种溶液固化快速成型制造方法 |
| WO2016061060A1 (en) * | 2014-10-16 | 2016-04-21 | Dow Global Technologies Llc | Method for additive manufacturing |
| WO2016086216A1 (en) * | 2014-11-27 | 2016-06-02 | Georgia-Pacific Chemicals Llc | Thixotropic, thermosetting resins for use in a material extrusion process in additive manufacturing |
| CN105818369B (zh) * | 2015-01-05 | 2019-06-14 | 三纬国际立体列印科技股份有限公司 | 立体打印机喷头 |
| US10688770B2 (en) * | 2015-03-03 | 2020-06-23 | Ricoh Co., Ltd. | Methods for solid freeform fabrication |
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2016
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- 2016-06-02 WO PCT/IB2016/053246 patent/WO2016193933A1/en not_active Ceased
- 2016-06-02 JP JP2017562687A patent/JP6628814B2/ja not_active Expired - Fee Related
- 2016-06-02 EP EP16731331.1A patent/EP3302938A1/en not_active Withdrawn
- 2016-06-02 KR KR1020187000209A patent/KR20180014160A/ko not_active Withdrawn
- 2016-06-02 US US15/579,348 patent/US20180147773A1/en not_active Abandoned
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| WO2016193933A1 (en) | 2016-12-08 |
| CN107848197A (zh) | 2018-03-27 |
| JP2018519186A (ja) | 2018-07-19 |
| US20180147773A1 (en) | 2018-05-31 |
| EP3302938A1 (en) | 2018-04-11 |
| KR20180014160A (ko) | 2018-02-07 |
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