JP2009521560A - 二段階硬化ポリイミドオリゴマー - Google Patents
二段階硬化ポリイミドオリゴマー Download PDFInfo
- Publication number
- JP2009521560A JP2009521560A JP2008547404A JP2008547404A JP2009521560A JP 2009521560 A JP2009521560 A JP 2009521560A JP 2008547404 A JP2008547404 A JP 2008547404A JP 2008547404 A JP2008547404 A JP 2008547404A JP 2009521560 A JP2009521560 A JP 2009521560A
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- JP
- Japan
- Prior art keywords
- polyamic acid
- aromatic
- acid oligomer
- dianhydride
- solution
- 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.)
- Granted
Links
- 229920001721 polyimide Polymers 0.000 title claims abstract description 43
- 239000004642 Polyimide Substances 0.000 title claims abstract description 40
- 239000002131 composite material Substances 0.000 claims abstract description 61
- 229920005575 poly(amic acid) Polymers 0.000 claims abstract description 37
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 25
- 239000000126 substance Substances 0.000 claims abstract description 20
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 239000011800 void material Substances 0.000 claims abstract description 18
- 238000013006 addition curing Methods 0.000 claims abstract description 16
- 239000000853 adhesive Substances 0.000 claims abstract description 8
- 230000001070 adhesive effect Effects 0.000 claims abstract description 8
- 239000000463 material Substances 0.000 claims description 35
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 23
- 150000004984 aromatic diamines Chemical class 0.000 claims description 21
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 claims description 17
- 150000004985 diamines Chemical class 0.000 claims description 17
- 239000000835 fiber Substances 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 10
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 claims description 9
- 229920001971 elastomer Polymers 0.000 claims description 9
- 239000003733 fiber-reinforced composite Substances 0.000 claims description 9
- 239000005060 rubber Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 claims description 5
- 229940018564 m-phenylenediamine Drugs 0.000 claims description 5
- 229920002379 silicone rubber Polymers 0.000 claims description 5
- 239000004945 silicone rubber Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- ZBMISJGHVWNWTE-UHFFFAOYSA-N 3-(4-aminophenoxy)aniline Chemical group C1=CC(N)=CC=C1OC1=CC=CC(N)=C1 ZBMISJGHVWNWTE-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000012779 reinforcing material Substances 0.000 claims description 3
- DKKYOQYISDAQER-UHFFFAOYSA-N 3-[3-(3-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=C(OC=3C=C(N)C=CC=3)C=CC=2)=C1 DKKYOQYISDAQER-UHFFFAOYSA-N 0.000 claims description 2
- -1 3-aminophenoxy Chemical group 0.000 claims description 2
- KHYXYOGWAIYVBD-UHFFFAOYSA-N 4-(4-propylphenoxy)aniline Chemical compound C1=CC(CCC)=CC=C1OC1=CC=C(N)C=C1 KHYXYOGWAIYVBD-UHFFFAOYSA-N 0.000 claims description 2
- WUPRYUDHUFLKFL-UHFFFAOYSA-N 4-[3-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(OC=2C=CC(N)=CC=2)=C1 WUPRYUDHUFLKFL-UHFFFAOYSA-N 0.000 claims description 2
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- RSFFTZBPSXWHRR-UHFFFAOYSA-N 4-(4-propylphenoxy)phthalic acid Chemical compound C1=CC(CCC)=CC=C1OC1=CC=C(C(O)=O)C(C(O)=O)=C1 RSFFTZBPSXWHRR-UHFFFAOYSA-N 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 239000007859 condensation product Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000003457 sulfones Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 58
- 239000011347 resin Substances 0.000 description 36
- 229920005989 resin Polymers 0.000 description 36
- 238000001723 curing Methods 0.000 description 19
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 18
- 238000005452 bending Methods 0.000 description 18
- XUSNPFGLKGCWGN-UHFFFAOYSA-N 3-[4-(3-aminopropyl)piperazin-1-yl]propan-1-amine Chemical compound NCCCN1CCN(CCCN)CC1 XUSNPFGLKGCWGN-UHFFFAOYSA-N 0.000 description 16
- 230000009477 glass transition Effects 0.000 description 14
- 239000002253 acid Substances 0.000 description 9
- 239000004744 fabric Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
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- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000006159 dianhydride group Chemical group 0.000 description 6
- 238000007689 inspection Methods 0.000 description 6
- 229920001187 thermosetting polymer Polymers 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- 150000003949 imides Chemical class 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000009719 polyimide resin Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000012783 reinforcing fiber Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000003039 volatile agent Substances 0.000 description 3
- KNDQHSIWLOJIGP-UMRXKNAASA-N (3ar,4s,7r,7as)-rel-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione Chemical compound O=C1OC(=O)[C@@H]2[C@H]1[C@]1([H])C=C[C@@]2([H])C1 KNDQHSIWLOJIGP-UMRXKNAASA-N 0.000 description 2
- ZHBXLZQQVCDGPA-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)sulfonyl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(S(=O)(=O)C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 ZHBXLZQQVCDGPA-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
- 150000007513 acids Chemical class 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- NIDNOXCRFUCAKQ-UHFFFAOYSA-N bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical class C1C2C=CC1C(C(=O)O)C2C(O)=O NIDNOXCRFUCAKQ-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000008439 repair process Effects 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 239000002759 woven fabric Substances 0.000 description 2
- PMTMAFAPLCGXGK-JMTMCXQRSA-N (15Z)-12-oxophyto-10,15-dienoic acid Chemical compound CC\C=C/C[C@H]1[C@@H](CCCCCCCC(O)=O)C=CC1=O PMTMAFAPLCGXGK-JMTMCXQRSA-N 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- WCXGOVYROJJXHA-UHFFFAOYSA-N 3-[4-[4-(3-aminophenoxy)phenyl]sulfonylphenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(=CC=2)S(=O)(=O)C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 WCXGOVYROJJXHA-UHFFFAOYSA-N 0.000 description 1
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 1
- PMTMAFAPLCGXGK-UHFFFAOYSA-N OPDA Natural products CCC=CCC1C(CCCCCCCC(O)=O)C=CC1=O PMTMAFAPLCGXGK-UHFFFAOYSA-N 0.000 description 1
- 101100028078 Oryza sativa subsp. japonica OPR1 gene Proteins 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000005056 compaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
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- 239000003365 glass fiber Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000009787 hand lay-up Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000007731 hot pressing Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002648 laminated material Substances 0.000 description 1
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- 231100001231 less toxic Toxicity 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
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- 230000000717 retained effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
Classifications
-
- 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
- C08G73/1003—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
-
- 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
-
- 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
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
- C08G73/101—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents
-
- 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
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
- C08G73/101—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents
- C08G73/1014—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents in the form of (mono)anhydrid
-
- 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
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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
- C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino 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
- 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
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- C08G73/1046—Polyimides containing oxygen in the form of ether bonds in the main chain
- C08G73/105—Polyimides containing oxygen in the form of ether bonds in the main chain with oxygen only in the diamino moiety
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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
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- 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
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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
- C08G73/1067—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
-
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Abstract
【解決手段】ポリアミド酸オリゴマーおよびポリイミドオリゴマーを形成する反応において、付加硬化型末端停止物質としてシトラコン酸無水物およびイタコン酸無水物を使用する方法を提供する。得られたオリゴマーから作製されるプリプレグおよび高温接着剤、ならびに、前記プリプレグから作製される高温・低空隙容量複合材料も提供する。
【選択図】なし
Description
本願は、2003年9月2日に出願された米国仮特許出願第60/499,849号の優先権を主張する、2004年8月30日に出願された米国特許出願第10/931,070号の一部継続出願である。
本発明は、一般に、ポリアミド酸オリゴマーおよびポリイミドオリゴマーを形成する反応において、付加硬化型末端停止物質としてシトラコン酸無水物およびイタコン酸無水物を使用する方法に関するものである。本発明はまた、一般に、得られたオリゴマーから作製されるプリプレグおよび高温接着剤、ならびに、前記プリプレグから作製される高温・低空隙容量・繊維強化複合材料に関するものである。
強化繊維およびマトリックス樹脂から成る繊維強化複合材料は、軽量であり優れた機械的特性を有する。そのため、これらの複合材料は、航空宇宙用品、自動車用品、インフラ補修用品、船舶用品、軍需品、スポーツ用品、または、長年の過酷な使用に耐えるのに十分な強靱性と耐衝撃性を有することが必要とされる他の消費者製品など様々な構造的および非構造的用途に広く用いられてきた。
(1)少なくとも1種の二無水物(例えば、BPDA)と少なくとも一種のジアミン(例えば、BAPP)を、別々の反応容器に仕込み、
(2)一定量の適切な溶媒(例えば、1−メチル−2−ピロリジノン(NMP))を各反応容器に添加し、一方の容器では二無水物のスラリーまたは溶液を形成させ、他方の容器ではジアミンのスラリーまたは溶液を形成させ、
(3)各反応容器中のスラリーまたは溶液を、約50〜約120℃の範囲の温度まで加熱し、前記二無水物およびジアミンを溶解し、
(4)各反応容器中の溶液を周囲の温度または室温まで冷却し、
(5)前記二無水物溶液を前記ジアミン溶液に、約10〜約60分間かけて徐々に添加し、
(6)付加硬化型末端停止物質溶液(例えば、NMP中シトラコン酸無水物(CA))を前記反応容器に添加し、そして
(7)前記溶液を約15〜約120分間攪拌し、アミド酸溶液を形成させ、この場合、このアミド酸溶液中の二無水物対ジアミン対付加硬化型末端停止物質のモル比が、約1.0/1.95/2.10〜約1.0/2.1/2.0の範囲にある。
(1)約20〜約40重量%(好ましくは約25〜約35重量%)のアミド酸溶液および約60〜約80重量%(好ましくは約65〜約75重量%)の共沸剤(例えば、トルエン)を反応容器に入れ、
(2)約0.05〜約0.5重量%(好ましくは約0.1〜約0.2重量%)の強酸性触媒(例えば、メタンスルホン酸)を反応容器に仕込み、混合物を形成し、
(3)反応容器中の混合物を、約100〜約130℃(好ましくは約120〜約125℃)の温度になるまで約2〜約6時間加熱し、
(4)前記混合物を周囲の温度または室温まで冷却し、
(5)反応容器から共沸剤を除去し、そして
(6)反応容器中に含まれる残留溶液から固形物、すなわちイミド粉末を単離し回収する。
(i) BPDA//3,4’−ODA/BAPP//CA、
(ii) BPDA//4,4’−ODA/BAPP//CA、
(iii)BTDA//3,4’−ODA/BAPP//CA、
(iv) BPDA//3,4’−ODA/m−APB//CA、および
(v) BPDA//3,4’−ODA/BAPP//IA。
曲げ強度(MPa):
曲げ強度は、ASTM D−790に従って測定した。
ガラス転移温度(Tg):
ガラス転移温度は、動的粘弾性測定装置(DMA)を用いて窒素雰囲気中2℃/分の昇温速度で測定した。
BPDA/CA(83/34)//3,4’−ODA/BAPP(85/15)
実施例1〜8において、成分3,4’−ODA(34.000g、0.170mol)、BAPP(12.300g、0.030mol)およびNMP(104.15g)を、機械攪拌機およびヒータを備えた500ミリリッター(ml)の三つ口フラスコに添加した。得られた混合物を完全に溶解し、溶液とした。BPDA(48.804g、0.166mol)を、NMP(104.15g)に分散させ、得られた分散液を上記三つ口フラスコ内の溶液に添加した。つぎに、得られた混合物を、毎分80回転(rpm)の速度で、60℃で8時間攪拌し、溶液を得た。最後に、NMP(10.0g)中CA(7.616g、0.068mol)溶液を前記三つ口フラスコ内の溶液に添加し、得られた混合物を60℃で2時間攪拌した。固形分30重量%、粘度31ポアズのプリプレグ溶液を得た。
BPDA/CA(83/34)//4,4’−ODA/BAPP(85/15)
本実施例では、芳香族ジアミン3,4’−ODAの代わりに、芳香族ジアミン4,4’−ODAを使用した。プリプレグ溶液は、固形分が30重量%であり、粘度は64ポアズであった。複合材料検査結果を表2に示す。
BPDA/CA(80/40)//4,4’−ODA/BAPP(50/50)
これらの実施例では、芳香族酸二無水物の末端停止物質に対する比率および芳香族ジアミン4,4’−ODAの芳香族ジアミンBAPPに対する比率を、それぞれ80/40および50/50に変更した。プリプレグ溶液は、固形分が30重量%であり、粘度は28ポアズであった。複合材料検査結果を表3に示す。
BTDA/CA(83/34)//3,4’−ODA/BAPP(85/15)
実施例1〜8で使用した芳香族酸二無水物BPDAの代わりに、これらの実施例では、芳香族酸二無水物BTDAを使用した。プリプレグ溶液は、固形分が30重量%であり、粘度は32ポアズであった。複合材料検査結果を表4に示す。
BPDA/CA(83/34)//3,4’−ODA/m−APB(85/15)
実施例1〜8で使用した芳香族ジアミンBAPPの代わりに、本実施例では、芳香族ジアミンm−APBを使用した。プリプレグ溶液は、固形分が30重量%であり、粘度は33ポアズであった。複合材料検査結果を表5に示す。
BPDA/IA(83/34)//3,4’−ODA/BAPP(85/15)
実施例1〜8で使用した末端停止物質CAの代わりに、本実施例では、末端停止物質IAを使用した。プリプレグ溶液は、固形分が30重量%であり、粘度は31ポアズであった。複合材料検査結果を表6に示す。
スカイボンド(SKYBOND)1000
これらの比較例では、サイテック・エンジニアド・マテリアルズから入手したカーボン織布シート8枚に、インダストリアル・サミット・テクノロジー社(Industrial Summit Technology Corporation)(500 チーズクエーク・ロード、パーリン、ニュージャージー州 08859(500 Cheesequake Road,Parlin,NJ 08859))から製品名スカイボンド1000として入手したポリイミド前駆体の溶液を以下の条件で含浸させた。すなわち、各シートをスカイボンド1000プリプレグ溶液でぬらした後、80℃で20分間乾燥させた。つぎに、この乾燥させたシートを以下のスケジュールに従ってイミド化した。すなわち、120℃で1時間、150℃で0.5時間、200℃で1時間、および225℃で1時間。つぎに、この乾燥させイミド化したシートを、株式会社東洋精機製作所製の11×18cmホットプレス機(モデルNo.MP−SCH)に並べ、初期圧力4.2MPaをかけ、下記の表7に記載した硬化処理を行った。この初期圧力は、硬化温度の上昇に伴い、経時的に5〜6MPaまで増加させた。このプロセスを2回繰り返した。得られた複合材料の硬化樹脂とカーボン布の合計に対する硬化樹脂の重量パーセント([硬化樹脂]/{[硬化樹脂]+[カーボン布]})は、35〜40重量%の範囲であった。これらの複合材料は、調製後、曲げ強度およびガラス転移温度の検査を行い、その結果を表7に示した。
スカイボンド(SKYBOND)2000
スカイボンド1000プリプレグ溶液の代わりに、比較例C−4〜C−8では、実施例C−1〜C−3に関して詳細に上述した手順、条件などに従ってスカイボンド(SKYBOND)2000プリプレグ溶液を用いて調製した。複合材料検査結果を表8に示す。
Claims (21)
- シトラコン酸無水物およびイタコン酸無水物を使用する方法であって、ポリアミド酸オリゴマーおよびポリイミドオリゴマーを形成する反応において、シトラコン酸無水物およびイタコン酸無水物を付加硬化型末端停止物質として使用することを含む方法。
- ポリアミド酸オリゴマーであって、1種以上の芳香族酸二無水物と、1種以上の芳香族ジアミンと、シトラコン酸無水物およびイタコン酸無水物から成る群から選択される1種以上の付加硬化型末端停止物質とを反応させることにより得られるポリアミド酸オリゴマー。
- 前記芳香族酸二無水物が、その化学構造中に二つ以上の芳香環を有する、請求項2に記載のポリアミド酸オリゴマー。
- 前記芳香族酸二無水物が、式(I)によって表され、1,2,4,5−ベンゼンテトラカルボン酸二無水物を含む、請求項4に記載のポリアミド酸オリゴマー。
- 前記芳香族酸二無水物が、式(II)によって表され、3,3’,4,4’−ビフェニルテトラカルボン酸二無水物、2,2’−ビス[4−(3,4−ジカルボキシフェノキシ)フェニル]プロパン二無水物、1,1’,2,2’−ベンゾフェノンテトラカルボン酸二無水物、4,4’−オキシジフタル酸無水物、3,3’,4,4’−ジフェニルスルホンテトラカルボン酸二無水物、およびそれらの混合物を含む群から選択される、請求項4に記載のポリアミド酸オリゴマー。
- 樹脂が、2種の芳香族酸二無水物と、1種以上の芳香族ジアミンと、シトラコン酸無水物およびイタコン酸無水物から成る群から選択される1種以上の付加硬化型末端停止物質との反応生成物であり、第一の二無水物は、前記2種の芳香族酸二無水物の総重量に対して約5〜約40重量%の範囲の量で存在し、第二の二無水物は、前記2種の芳香族酸二無水物の総重量に対して約60〜約95重量%の範囲の量で存在している、請求項2に記載のポリアミド酸オリゴマー。
- 前記芳香族ジアミンが、その化学構造中に少なくとも一つのエーテル結合を有する、請求項2に記載のポリアミド酸オリゴマー。
- 前記芳香族ジアミンが、3,4’−オキシジアニリン、4,4’−オキシジアニリン、m−フェニレンジアミン、2,2’−ビス[4−(4−アミノフェノキシ)フェニル]プロパン、ビス[4−(3−アミノフェノキシ)フェニル]スルホン、1,3−ビス(3−アミノフェノキシ)ベンゼン、1,3−ビス(4−アミノフェノキシ)ベンゼン、およびそれらの混合物から成る群から選択される、請求項8に記載のポリアミド酸オリゴマー。
- 前記オリゴマーが、1種以上の芳香族酸二無水物と、2種の芳香族ジアミンと、シトラコン酸無水物およびイタコン酸無水物から成る群から選択される1種以上の付加硬化型末端停止物質との反応生成物であり、少なくとも1種のジアミンが、その化学構造中に一つ以上の酸素結合を有しており、前記2種の芳香族ジアミンの総重量に対して少なくとも50重量%の量で存在している、請求項2に記載のポリアミド酸オリゴマー。
- 前記芳香族ジアミンが、ゴム成分との組み合わせで使用される、請求項2に記載のポリアミド酸オリゴマー。
- 前記ゴム成分が、アミンを末端に有するゴムである、請求項11に記載のポリアミド酸オリゴマー。
- 前記アミンを末端に有するゴムが、アミンを末端に有するシリコーンゴムである、請求項12に記載のポリアミド酸オリゴマー。
- 前記アミンを末端に有するシリコーンゴムが、前記芳香族ジアミンおよびシリコーンゴムの総重量に対して約30重量%未満の量で存在する、請求項13に記載のポリアミド酸オリゴマー。
- 請求項2に記載のポリアミド酸オリゴマーを縮合させることによって得られるポリイミドオリゴマーであって、前記ポリイミドオリゴマーが、約370℃以下の温度で硬化する、ポリイミドオリゴマー。
- (a)ポリアミド酸オリゴマーおよびポリイミドオリゴマーのうち少なくとも1つと、(b)1種以上の有機溶媒とを含む溶液であって、前記ポリアミド酸オリゴマーが、1種以上の芳香族酸二無水物と、1種以上の芳香族ジアミンと、シトラコン酸無水物およびイタコン酸無水物から成る群から選択される1種以上の付加硬化型末端停止物質とを反応させることにより得られ、前記ポリイミドオリゴマーが、前記ポリアミド酸オリゴマーの縮合生成物である、溶液。
- 前記オリゴマーが、約25重量%以上の濃度で前記溶液中に存在し、前記溶液の粘度が、約10〜約140ポアズの範囲である、請求項16に記載の溶液。
- 繊維強化材に請求項16に記載の溶液を含浸させたプリプレグを圧密硬化させることにより得られる高温・低空隙容量・繊維強化複合材料。
- 前記複合材料の体積の約1〜約2パーセントの範囲の空隙容量を有する、請求項18に記載の高温・低空隙容量・繊維強化複合材料。
- 前記複合材料の体積の約0.5〜約1.5パーセントの範囲の空隙容量を有する、請求項19に記載の高温・低空隙容量・繊維強化複合材料。
- 請求項16に記載の溶液から製造される接着剤。
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Cited By (3)
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KR101397703B1 (ko) | 2011-12-26 | 2014-05-22 | 제일모직주식회사 | 폴리아미드 수지, 이의 제조 방법, 및 이를 포함하는 물품 |
WO2016147997A1 (ja) * | 2015-03-19 | 2016-09-22 | 三菱瓦斯化学株式会社 | ポリイミド樹脂 |
WO2018180930A1 (ja) * | 2017-03-30 | 2018-10-04 | 株式会社カネカ | セミプレグ、プリプレグ、樹脂複合材料およびそれらの製造方法 |
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KR20200082278A (ko) * | 2018-12-28 | 2020-07-08 | 주식회사 두산 | 폴리아믹산 조성물, 및 이를 이용한 투명 폴리이미드 필름 |
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Cited By (9)
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KR101397703B1 (ko) | 2011-12-26 | 2014-05-22 | 제일모직주식회사 | 폴리아미드 수지, 이의 제조 방법, 및 이를 포함하는 물품 |
WO2016147997A1 (ja) * | 2015-03-19 | 2016-09-22 | 三菱瓦斯化学株式会社 | ポリイミド樹脂 |
JP6037088B1 (ja) * | 2015-03-19 | 2016-11-30 | 三菱瓦斯化学株式会社 | ポリイミド樹脂 |
KR101841977B1 (ko) | 2015-03-19 | 2018-03-26 | 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 | 폴리이미드 수지 |
US10174167B2 (en) | 2015-03-19 | 2019-01-08 | Mitsubishi Gas Chemical Company, Inc. | Polyimide resin |
WO2018180930A1 (ja) * | 2017-03-30 | 2018-10-04 | 株式会社カネカ | セミプレグ、プリプレグ、樹脂複合材料およびそれらの製造方法 |
JPWO2018180930A1 (ja) * | 2017-03-30 | 2020-02-06 | 株式会社カネカ | セミプレグ、プリプレグ、樹脂複合材料およびそれらの製造方法 |
JP7016082B2 (ja) | 2017-03-30 | 2022-02-04 | 株式会社カネカ | セミプレグ、プリプレグ、樹脂複合材料およびそれらの製造方法 |
US11492446B2 (en) | 2017-03-30 | 2022-11-08 | Kaneka Corporation | Semipreg, prepreg, resin composite material, and production methods thereof |
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