CN105601920B - 一种含芴或芴酮结构的聚酰亚胺纳米复合材料及其制备方法和应用 - Google Patents
一种含芴或芴酮结构的聚酰亚胺纳米复合材料及其制备方法和应用 Download PDFInfo
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- 229920001721 polyimide Polymers 0.000 title claims abstract description 67
- 239000004642 Polyimide Substances 0.000 title claims abstract description 65
- 239000002114 nanocomposite Substances 0.000 title claims abstract description 34
- 239000000463 material Substances 0.000 title claims abstract description 28
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 150000002220 fluorenes Chemical class 0.000 title abstract 5
- 239000003292 glue Substances 0.000 claims abstract description 26
- 239000002105 nanoparticle Substances 0.000 claims abstract description 25
- 229920005575 poly(amic acid) Polymers 0.000 claims abstract description 17
- 238000004806 packaging method and process Methods 0.000 claims abstract description 6
- 150000004984 aromatic diamines Chemical class 0.000 claims abstract description 4
- 239000002994 raw material Substances 0.000 claims abstract description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 44
- 239000002131 composite material Substances 0.000 claims description 42
- 238000010438 heat treatment Methods 0.000 claims description 37
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 25
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 21
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 claims description 16
- 239000011521 glass Substances 0.000 claims description 16
- 229960001545 hydrotalcite Drugs 0.000 claims description 16
- 229910001701 hydrotalcite Inorganic materials 0.000 claims description 16
- 239000004952 Polyamide Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- 150000004985 diamines Chemical class 0.000 claims description 14
- 229920002647 polyamide Polymers 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 14
- 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 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 238000001816 cooling Methods 0.000 claims description 11
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 11
- 229910052901 montmorillonite Inorganic materials 0.000 claims description 11
- 229910021389 graphene Inorganic materials 0.000 claims description 10
- 239000010445 mica Substances 0.000 claims description 10
- 229910052618 mica group Inorganic materials 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- 239000012300 argon atmosphere Substances 0.000 claims description 8
- 239000006185 dispersion Substances 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 238000007790 scraping Methods 0.000 claims description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 4
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 claims description 4
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 claims description 4
- ZNOKGRXACCSDPY-UHFFFAOYSA-N tungsten trioxide Chemical compound O=[W](=O)=O ZNOKGRXACCSDPY-UHFFFAOYSA-N 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- WRFWTYGMKIUAKL-UHFFFAOYSA-N 3-methylphenol Chemical compound CC1=CC=CC(O)=C1.CC1=CC=CC(O)=C1 WRFWTYGMKIUAKL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052582 BN Inorganic materials 0.000 claims description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 claims description 2
- 229910021555 Chromium Chloride Inorganic materials 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- ROUIDRHELGULJS-UHFFFAOYSA-N bis(selanylidene)tungsten Chemical compound [Se]=[W]=[Se] ROUIDRHELGULJS-UHFFFAOYSA-N 0.000 claims description 2
- NGTSQWJVGHUNSS-UHFFFAOYSA-N bis(sulfanylidene)vanadium Chemical compound S=[V]=S NGTSQWJVGHUNSS-UHFFFAOYSA-N 0.000 claims description 2
- FBGGJHZVZAAUKJ-UHFFFAOYSA-N bismuth selenide Chemical compound [Se-2].[Se-2].[Se-2].[Bi+3].[Bi+3] FBGGJHZVZAAUKJ-UHFFFAOYSA-N 0.000 claims description 2
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 claims description 2
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- ZZEMEJKDTZOXOI-UHFFFAOYSA-N digallium;selenium(2-) Chemical compound [Ga+3].[Ga+3].[Se-2].[Se-2].[Se-2] ZZEMEJKDTZOXOI-UHFFFAOYSA-N 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 2
- RQQRAHKHDFPBMC-UHFFFAOYSA-L lead(ii) iodide Chemical compound I[Pb]I RQQRAHKHDFPBMC-UHFFFAOYSA-L 0.000 claims description 2
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 claims description 2
- 229910001623 magnesium bromide Inorganic materials 0.000 claims description 2
- 238000004377 microelectronic Methods 0.000 claims description 2
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052982 molybdenum disulfide Inorganic materials 0.000 claims description 2
- BQBYSLAFGRVJME-UHFFFAOYSA-L molybdenum(2+);dichloride Chemical compound Cl[Mo]Cl BQBYSLAFGRVJME-UHFFFAOYSA-L 0.000 claims description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 2
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
- PJYXVICYYHGLSW-UHFFFAOYSA-J tetrachloroplumbane Chemical compound Cl[Pb](Cl)(Cl)Cl PJYXVICYYHGLSW-UHFFFAOYSA-J 0.000 claims description 2
- SWFBFRDZBFXEHJ-UHFFFAOYSA-N titanium diselenide Chemical compound [Se]=[Ti]=[Se] SWFBFRDZBFXEHJ-UHFFFAOYSA-N 0.000 claims description 2
- CFJRPNFOLVDFMJ-UHFFFAOYSA-N titanium disulfide Chemical compound S=[Ti]=S CFJRPNFOLVDFMJ-UHFFFAOYSA-N 0.000 claims description 2
- ITRNXVSDJBHYNJ-UHFFFAOYSA-N tungsten disulfide Chemical compound S=[W]=S ITRNXVSDJBHYNJ-UHFFFAOYSA-N 0.000 claims description 2
- 240000007594 Oryza sativa Species 0.000 claims 1
- 235000007164 Oryza sativa Nutrition 0.000 claims 1
- 235000013339 cereals Nutrition 0.000 claims 1
- 235000009566 rice Nutrition 0.000 claims 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims 1
- 238000001291 vacuum drying Methods 0.000 claims 1
- 230000004888 barrier function Effects 0.000 abstract description 8
- 230000000694 effects Effects 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 2
- 230000037361 pathway Effects 0.000 abstract 1
- 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 description 17
- 238000010521 absorption reaction Methods 0.000 description 10
- 239000012528 membrane Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 150000008064 anhydrides Chemical class 0.000 description 4
- 238000005452 bending Methods 0.000 description 4
- 229920005570 flexible polymer Polymers 0.000 description 4
- VTDXHXOFPBQISQ-UHFFFAOYSA-N 2-(4-aminobenzoyl)oxyethyl 4-aminobenzoate Chemical compound C1=CC(N)=CC=C1C(=O)OCCOC(=O)C1=CC=C(N)C=C1 VTDXHXOFPBQISQ-UHFFFAOYSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 229910018516 Al—O Inorganic materials 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229910018557 Si O Inorganic materials 0.000 description 2
- 229910002808 Si–O–Si Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 150000002466 imines Chemical group 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000009210 therapy by ultrasound Methods 0.000 description 2
- XVCKCCODMHCXJD-UHFFFAOYSA-N (4-aminophenyl)urea Chemical compound NC(=O)NC1=CC=C(N)C=C1 XVCKCCODMHCXJD-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- QIKYZXDTTPVVAC-UHFFFAOYSA-N 4-Aminobenzamide Chemical compound NC(=O)C1=CC=C(N)C=C1 QIKYZXDTTPVVAC-UHFFFAOYSA-N 0.000 description 1
- -1 N' - ((9H-fluorene-2,7-diyl) bis (oxy)) bis (ethane-2,1-diyl) Chemical group 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 150000003949 imides Chemical group 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 229920006280 packaging film Polymers 0.000 description 1
- 239000012785 packaging film Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000005476 size effect Effects 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
Classifications
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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
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
-
- 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
-
- 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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- 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
- C08K3/02—Elements
- C08K3/04—Carbon
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- 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
- C08K3/34—Silicon-containing compounds
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- 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
- C08K3/34—Silicon-containing compounds
- C08K3/346—Clay
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
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- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
本发明公开的是一种含芴或芴酮结构的聚酰亚胺纳米复合材料及其制备方法和应用。本发明通过采用具有高平面性含芴或芴酮结构的芳香二胺、各种四酸二酐和层状纳米粒子为原料,反应得到聚酰胺酸纳米复合胶液,然后进行酰亚胺化得到聚酰亚胺纳米复合材料。由于所选取的含有芴或芴酮结构的芳香二胺具有较好平面性和刚性,因此所制备的聚酰亚胺具有较小的自由体积,再结合层状纳米粒子的延长渗透路径效应,能够使该聚酰亚胺纳米复合材料具有优异的阻隔性能、热稳定性和优异的综合性能。本发明的制备工艺简单、多样,因而适于工业生产;本发明所公开的含芴或芴酮结构的聚酰亚胺纳米复合材料可应用于高性能包装与防护以及电子器件封装等高新技术产业领域。
Description
技术领域
本发明涉及材料科学领域,特别是一种含芴或芴酮结构的聚酰亚胺纳米复合材料及其制备方法和应用。
技术背景
随着科技的不断发展,由柔性聚合物作为衬底和封装层的柔性电子器件应运而生,最具代表性的柔性电子器件为有机电致发光器件(OLED)和有机太阳能电池(OPV),然而限制它们迅速发展的主要原因之一是柔性聚合物材料的性能无法满足其正常使用及较长使用寿命,主要表现在耐热性不足、热尺寸稳定性较差,更为重要的是其阻隔性能不能满足柔性有机电子器件的苛刻要求。纳米粒子由于具有的表面积效应、量子尺寸效应及宏观量子隧道等效应,能够影响聚合物链段运动、分子链之间相互作用和相结构,使聚合物纳米复合材料具有许多特殊的优异性能,如优异的力学性能、耐热性和尺寸稳定性等,尤其是层状纳米粒子可在二维方向上限制各种气体的渗透,从而显著地提高复合材料的阻隔性能。因此,制备聚合物纳米复合材料作为柔性衬底或封装层成为解决OLED和OPV等电子器件发展的关键技术之一,众多研究人员在这一领域取得了显著的成果(如专利CN103692743A、CN103897244A、CN104494249A)。
在众多聚合物基体中,聚酰亚胺(PI)由于具有其它柔性聚合物材料所无法比拟优异性能,如突出的耐高温和低温性能;力学性能好、机械强度高;抗蠕变能力强,摩擦性能优良;独特的光电性能、优异的绝缘性能;化学稳定性好、耐有机溶剂、耐辐射性、阻隔性能优良等,成为柔性聚合物封装薄膜的最佳选择之一。并且,根据相关的文献报道,当聚合物链段平面性较高时,其堆砌密度越大,自由体积越小,阻隔性能越好。前期我们合成了若干含芴或芴酮结构的二胺单体具有较高的平面性,利用这些新型的二胺单体与商业化的二酐聚合所得到的聚酰亚胺具有比普通聚酰亚胺更为优异的阻隔性能。本设计将具有层状结构的纳米粒子(如石墨烯、蒙脱土、云母片和水滑石等)与含芴或芴酮结构的二胺和各种商业化的四酸二酐混合制备聚酰亚胺纳米复合材料,结合含平面结构聚酰亚胺本征型的高阻隔性和层状纳米粒子的延长渗透路径效应,从而获得一类阻隔性能出众,耐热性优异,热尺寸稳定性较好且综合性能极佳的聚酰亚胺纳米复合材料。然而,目前对于层状纳米粒子增强含芴或芴酮等高平面性结构的聚酰亚胺纳米复合材料研究较少,因此,有必要开展此类聚酰亚胺纳米复合材料的研究。
发明内容
本发明的目的是提供一种含芴或芴酮结构的聚酰亚胺纳米复合材料及其制备方法和应用。
本发明的技术方案如下:
一种含芴或芴酮结构的聚酰亚胺纳米复合材料,其特征在于:采用具有高平面性含芴或芴酮结构的芳香二胺、各种四酸二酐和层状纳米粒子为原料,二胺与二酐按摩尔比为1:(0.9~1.1),层状纳米粒子的质量为二胺和二酐总质量的0.05~30%。
本发明的另外技术特征是:
专利中二胺的分子结构通式为:
其中,Z为或Ar1选自下列结构式中的任何一种:
其中,Ar2、Ar3、Ar4选自下列结构式中的任何一种:
其中Ar5和Ar6选自下列结构式中的任何一种:
其中,m=1,2,3,4,6,8;n1,n2=1,2,3,4,5,6
专利中二酐的分子结构式如下所示:
专利中层状纳米粒子可以为蒙脱土、石墨烯、云母片或水滑石,以及具有层状结构的氮化硼、氮化碳、黑磷、氧化铁、二氧化锰、三氧化钼、三氧化钨、五氧化二钒、二硫化钼、二硫化钨、二硫化钛、二硫化钒、硒化镓、二硒化钨、二硒化钛、硒化铋、二碘化铅、溴化镁、二氯化钼、氯化铬、四氯化铅和三氯化钌中的一种或多种混合物。
专利中强极性非质子有机溶剂为N-甲基吡咯烷酮、二甲基亚砜、二甲基砜、环丁砜、1,4-二氧六环、N,N-二甲基乙酰胺、N,N-二甲基甲酰胺、间甲酚、四氢呋喃中的一种或一种以上的混合物;
专利中聚酰胺酸复合胶液的制备方法包括以下两种方法:步骤(A1)、在氩气气氛中,将层状纳米粒子在强极性非质子有机溶剂中超声分散0.5~10h,制备一定浓度的纳米粒子均匀分散液;(A2)、将二胺与二酐按摩尔比为1:(0.9~1.1)加入到强极性非质子有机溶剂中,在-10~40℃搅拌反应0.5~72h,得到均相、粘稠的聚酰胺酸胶液;(A3)、将纳米粒子分散液添加到聚酰胺酸胶液中搅拌0.1~10h;或者,步骤(B1)、在氩气气氛中,将层状纳米粒子在强极性非质子有机溶剂中超声分散0.5~10h后,将二胺与二酐按摩尔比为1:(0.9~1.1)加入到分散液中,在-10~40℃搅拌反应0.5~72h,得到均相、粘稠的聚酰胺酸复合胶液;
专利中脱水方法分为热酰亚胺化或化学酰亚胺化。其中热酰亚胺化的具体操作为:将含层状纳米粒子的聚酰胺酸复合胶液刮涂在玻璃板上,再将玻璃板置于真空烘箱中,抽真空,升温程序为:室温升温至100℃后恒温整个过程0.8~3h,从100℃升温至200℃后恒温整个过程0.8~2h,从200℃升温至300℃恒温整个过程0.8~2h,从300℃升温至350℃~500℃后恒温整个过程0.5~2h,冷却后可取出聚酰亚胺膜。其中化学酰亚胺化的具体操作为:在含层状纳米粒子的聚酰胺酸溶液中加入吡啶/乙酸酐、或三乙胺/乙酸酐、或乙酸钠/乙酸酐作为脱水剂,升温搅拌,加热至60~170℃继续搅拌0.5~6h,冷却至室温后倒入甲醇或丙酮中得到聚酰亚胺沉淀,过滤干燥,即得到聚酰亚胺粉体,再将聚酰亚胺粉体溶于N-甲基吡咯烷酮(NMP)、二甲基亚砜(DMSO)、N,N-二甲基乙酰胺(DMAc)、N,N-二甲基甲酰胺(DMF)、间甲酚(m-Cresol)或四氢呋喃(THF)中,加热至完全溶解后,将聚酰亚胺溶液刮涂在玻璃板上,70~200℃真空干燥去除溶剂,冷却后可取出聚酰亚胺纳米复合膜。
发明所提出的含芴或芴酮结构的聚酰亚胺纳米复合材料的制备方法,制备工艺简单且多样,条件要求低,因而适于工业生产。该类含芴或芴酮结构的聚酰亚胺纳米复合材料可应用于微电子、军工、航空航天、高性能包装与防护以及电子器件封装等高新技术产业领域。
附图说明
图1是实施例1~6所得聚合物的红外光谱图,其中:
a对应FAPDA/PMDA/Mica复合材料
b对应FUPDA/PMDA/MMT复合材料
c对应FPIPDA/PMDA/GO复合材料
d对应FEC2EPDA/PMDA/LDHs复合材料
e对应FEC2APDA/PMDA/LDHs复合材料
f对应FEC2APDA/PMDA/LDHs复合材料
从红外光谱图中可以看到:
从红外光谱图中可以看到,在1776和1723cm-1附近是亚胺环上羰基的不对称和对称伸缩振动,720cm-1附近是亚胺环上羰基的弯曲振动,1380cm-1附近是酰亚胺环的伸缩振动。a:1653cm-1处出现了酰胺羰基的特征吸收峰,1017cm-1附近强烈的吸收峰为Si-O-Si伸缩振动,400-800cm-1附近的峰为Al-O和Si-O的弯曲振动;b:1041cm-1附近为Si-O-Si伸缩振动,400-800cm-1附近的峰为Al-O和Si-O的弯曲振动;c:1706cm-1处为氧化石墨的羧基上的C=O的伸缩振动峰,在1652cm-1处的吸收峰属于C-O的弯曲振动吸收峰,1283cm-1附近的吸收峰为Ar-H的变形振动吸收峰,在1114cm-1处为C-O-C的振动吸收峰;d:3434cm-1附近很强的吸收峰为-OH的伸缩振动,1370cm-1为CO3 2-的反对称伸缩振动峰;e:3433cm-1附近很强的吸收峰为-OH的伸缩振动,1368cm-1为CO3 2-的反对称伸缩振动峰;f:3433cm-1附近很强的吸收峰为-OH的伸缩振动,1368cm-1为CO3 2-的反对称伸缩振动峰,这些都说明实施例1~6所示的复合材料都已成功合成。
具体实施方式
下面给出实例以对本发明作更详细的说明,有必要指出的是以下实施例不能解释为对发明保护范围的限制,该领域的技术熟练人员根据上述发明内容对本发明作出的一些非本质的改进和调整,仍应属于本发明的保护范围。
实施例1
室温下,在氩气氛围下,将0.20g云母(Mica)在43.51g(46.1ml)N,N-二甲基甲酰胺中超声1h,再将4.3450g(0.01mol)N2,N7-bis(4-aminophenyl)-9H-fluorene-2,7-dicarboxamide(FAPDA)和2.1812g(0.01mol)1,2,4,5-Benzenetetracarboxylicanhydride(1,2,4,5-均苯四甲酸二酐,PMDA)加入至N,N-二甲基甲酰胺中,固含量为13%,搅拌反应6h,获得均相粘稠的聚酰胺酸/云母复合胶液。再将聚酰胺酸/云母复合胶液刮涂在玻璃板上,再将玻璃板置于真空烘箱中,抽真空,升温程序为:室温升温至100℃后恒温整个过程1h→100℃升温至200℃后恒温整个过程1h→200℃升温至300℃恒温整个过程1h→300℃升温至420℃后恒温整个过程1.5h,冷却后可取出聚酰亚胺/云母复合膜。该聚酰亚胺复合材料膜(FAPDA/PMDA/Mica)的红外光谱图如附录一中a所示。本实施例中的芳香型功能聚酰亚胺(FAPDA/PMDA-PI)的分子结构式如下:
实施例2
室温下,在氩气氛围下,将0.18g蒙脱土(MMT)在45.51g(48.8ml)N,N-二甲基甲酰胺中超声2h,将4.78g(0.01mol)1,1'-(9-oxo-9H-fluorene-2,7-diyl)bis(3-(4-aminophenyl)urea)(FUPDA)和2.1812g(0.01mol)1,2,4,5-Benzenetetracarboxylicanhydride(1,2,4,5-均苯四甲酸二酐,PMDA)加入至N,N-二甲基甲酰胺中,固含量为13%,搅拌反应6h,获得均相粘稠的聚酰胺酸/蒙脱土复合胶液。再将聚酰胺酸/蒙脱土复合胶液刮涂在玻璃板上,再将玻璃板置于真空烘箱中,抽真空,升温程序为:室温升温至100℃后恒温整个过程1h→100℃升温至200℃后恒温整个过程1h→200℃升温至300℃恒温整个过程1h→300℃升温至420℃后恒温整个过程1.5h,冷却后可取出聚酰亚胺/蒙脱土复合膜。该聚酰亚胺/蒙脱土复合膜(FUPDA/PMDA/MMT)的红外光谱图如附录一中b所示。本实施例中的芳香型功能聚酰亚胺(FUPDA/PMDA-PI)的分子结构式如下:
实施例3
室温下,在氩气氛围下,将0.03g氧化石墨烯(GO)在49.92g(52.85ml)N,N-二甲基甲酰胺中超声6h得到氧化石墨烯分散液,同时,将5.3068g(0.01mol)N1,N1'-((9H-fluorene-2,7-diyl)bis(4,1-phenylene))bis(benzene-1,4-diamine)(FPIPDA)和2.1812g(0.01mol)1,2,4,5-Benzenetetracarboxylic anhydride(1,2,4,5-均苯四甲酸二酐,PMDA)加入至N,N-二甲基甲酰胺中,固含量为13%,搅拌反应6h,获得均相粘稠的聚酰胺酸胶液,再将氧化石墨烯分散液倒入聚酰胺酸胶液中得到聚酰胺酸/氧化石墨烯复合胶液。再将聚酰胺酸/氧化石墨烯复合胶液刮涂在玻璃板上,再将玻璃板置于真空烘箱中,抽真空,升温程序为:室温升温至100℃后恒温整个过程1h→100℃升温至200℃后恒温整个过程1h→200℃升温至300℃恒温整个过程1h→300℃升温至420℃后恒温整个过程1h,冷却后可取出聚酰亚胺/氧化石墨烯复合膜。该聚酰亚胺/氧化石墨烯复合膜(FPIPDA/PMDA/GO)的红外光谱图如附录一中c所示。本实施例中的芳香型功能聚酰亚胺(FPIPDA/PMDA-PI)的分子结构式如下:
实施例4
室温下,在氩气氛围下,将0.15g水滑石(LDHs)在49.51g(52.4ml)N,N-二甲基甲酰胺中超声4h,将5.2457g(0.01mol)((9H-fluorene-2,7-diyl)bis(oxy))bis(ethane-2,1-diyl)bis(4-aminobenzoate)(FEC2EPDA)和2.1812g(0.01mol)1,2,4,5-Benzenetetracarboxylic anhydride(1,2,4,5-均苯四甲酸二酐,PMDA)加入至N,N-二甲基甲酰胺中,固含量为13%,搅拌反应6h,获得均相粘稠的聚酰胺酸/水滑石复合胶液。再将聚酰胺酸/水滑石复合胶液刮涂在玻璃板上,再将玻璃板置于真空烘箱中,抽真空,升温程序为:室温升温至100℃后恒温整个过程1h→100℃升温至200℃后恒温整个过程1h→200℃升温至300℃恒温整个过程1h→300℃升温至400℃后恒温整个过程1h,冷却后可取出聚酰亚胺/水滑石复合膜。该聚酰亚胺/水滑石复合膜(FEC2EPDA/PMDA/LDHs)的红外光谱图如附录一中d所示。本实施例中的芳香型功能聚酰亚胺(FEC2EPDA/PMDA-PI)的分子结构式如下:
实施例5
室温下,在氩气氛围下,将0.15g水滑石(LDHs)在49.38g(52.3ml)N,N-二甲基甲酰胺中超声4h,将5.2261g(0.01mol)N,N'-(((9H-fluorene-2,7-diyl)bis(oxy))bis(ethane-2,1-diyl)bis(4-aminobenzamide)(FEC2APDA)和2.1812g(0.01mol)1,2,4,5-Benzenetetracarboxylic anhydride(1,2,4,5-均苯四甲酸二酐,PMDA)加入至N,N-二甲基甲酰胺中,固含量为13%,搅拌反应6h,获得均相粘稠的聚酰胺酸/水滑石复合胶液。再将聚酰胺酸/水滑石复合胶液刮涂在玻璃板上,再将玻璃板置于真空烘箱中,抽真空,升温程序为:室温升温至100℃后恒温整个过程1h→100℃升温至200℃后恒温整个过程1h→200℃升温至300℃恒温整个过程1h→300℃升温至400℃后恒温整个过程1h,冷却后可取出聚酰亚胺/水滑石复合膜。该聚酰亚胺/水滑石复合膜(FEC2APDA/PMDA/LDHs)的红外光谱图如附录一中d所示。本实施例中的芳香型功能聚酰亚胺(FEC2APDA/PMDA-PI)的分子结构式如下:
实施例6
以实施例5相同的方法制备聚酰胺酸/水滑石复合胶液,然后采用化学酰亚胺化制备聚酰亚胺,步骤如:在所得聚酰胺酸/水滑石复合胶液中加入5mL乙酸酐,继续搅拌,再缓慢加入2.5mL三乙胺,并升温至70℃,继续搅拌6h后冷却至室温,倒入甲醇中得到聚酰亚胺/水滑石复合材料沉淀,抽滤后干燥,即得到聚酰亚胺粉体。聚酰亚胺/水滑石复合材料(FEC2APDA/PMDA/LDHs)的红外光谱图如附录一中e所示。
Claims (11)
1.一种含芴或芴酮结构的聚酰亚胺纳米复合材料,其特征在于:采用具有高平面性含芴或芴酮结构的芳香二胺、四酸二酐和层状纳米粒子为原料,二胺与二酐摩尔比为1:(0.9~1.1),层状纳米粒子的质量为二胺和二酐总质量的0.05~30%,所述二胺的分子结构通式为:
其中,
Z为
Ar1选自下列结构式中的任何一种:
其中,Ar2、Ar3、Ar4选自下列结构式中的任何一种:
其中Ar5和Ar6选自下列结构式中的任何一种:
其中,m=1,2,3,4,6,8;n1,n2=1,2,3,4,5,6。
2.根据权利要求1所述含芴或芴酮结构的聚酰亚胺纳米复合材料,其特征在于:二酐的分子结构式如下所示:
。
3.根据权利要求1所述含芴或芴酮结构的聚酰亚胺纳米复合材料,其特征在于:层状纳米粒子为蒙脱土、石墨烯、云母片或水滑石,以及具有层状结构的氮化硼、氮化碳、黑磷、氧化铁、二氧化锰、三氧化钼、三氧化钨、五氧化二钒、二硫化钼、二硫化钨、二硫化钛、二硫化钒、硒化镓、二硒化钨、二硒化钛、硒化铋、二碘化铅、溴化镁、二氯化钼、氯化铬、四氯化铅和三氯化钌中的一种或多种混合物。
4.根据权利要求1所述含芴或芴酮结构的聚酰亚胺纳米复合材料,其特征在于:聚酰亚胺纳米复合材料用于制备成粉体或薄膜。
5.根据权利要求1所述含芴或芴酮结构的聚酰亚胺纳米复合材料,其特征在于:制备方法包括以下两种方法:步骤(A1)、在氩气气氛中,将层状纳米粒子在强极性非质子有机溶剂中超声分散0.5~10h,制备浓度0.05~30%的纳米粒子均匀分散液;(A2)、将二胺与二酐按摩尔比为1:(0.9~1.1)加入到强极性非质子有机溶剂中,在-10~40℃搅拌反应0.5~72h,得到均相、粘稠的聚酰胺酸胶液;(A3)、将纳米粒子分散液添加到聚酰胺酸胶液中搅拌0.1~10h;(A4)、对含层状纳米粒子的聚酰胺酸复合胶液进行脱水,得到聚酰亚胺纳米复合材料;或者,步骤(B1)、在氩气气氛中,将层状纳米粒子在强极性非质子有机溶剂中超声分散0.5~10h后,将二胺与二酐按摩尔比为1:(0.9~1.1)加入到分散液中,在-10~40℃搅拌反应0.5~72h,得到均相、粘稠的聚酰胺酸复合胶液;(B2)、对含层状纳米粒子的聚酰胺酸复合胶液中的聚酰胺酸进行脱水,得到聚酰亚胺纳米复合材料。
6.根据权利要求5所述含芴或芴酮结构的聚酰亚胺纳米复合材料,其特征在于:聚酰胺酸复合胶液中纳米粒子、二胺和二酐总质量占反应物料总质量的2~50%。
7.根据权利要求5所述含芴或芴酮结构的聚酰亚胺纳米复合材料,其特征在于:强极性非质子有机溶剂为N-甲基吡咯烷酮、二甲基亚砜、二甲基砜、环丁砜、1,4-二氧六环、N,N-二甲基乙酰胺、N,N-二甲基甲酰胺、间甲酚、四氢呋喃中的一种或一种以上的混合物。
8.根据权利要求5所述含芴或芴酮结构的聚酰亚胺纳米复合材料,其特征在于:聚酰胺酸脱水得到聚酰亚胺的方法是热酰亚胺化或化学酰亚胺化。
9.根据权利要求8所述含芴或芴酮结构的聚酰亚胺纳米复合材料,其特征在于:热酰亚胺化的具体操作为:将含有层状米粒子的聚酰胺酸复合胶液刮涂在玻璃板上,再将玻璃板置于真空烘箱中,抽真空,升温程序为:室温升温至100℃后恒温整个过程0.8~3h,从100℃升温至200℃后恒温整个过程0.8~2h,从200℃升温至300℃恒温整个过程0.8~2h,从300℃升温至350℃~500℃后恒温整个过程0.5~2h,冷却后可取出聚酰亚胺膜。
10.根据权利要求8所述含芴或芴酮结构的聚酰亚胺纳米复合材料,其特征在于:化学酰亚胺化的具体操作为:在含有层状纳米粒子的聚酰胺酸复合胶液中加入吡啶/乙酸酐、或三乙胺/乙酸酐、或乙酸钠/乙酸酐作为脱水剂,升温搅拌,加热至60~170℃继续搅拌0.5~6h,冷却至室温后倒入甲醇或丙酮中得到聚酰亚胺沉淀,过滤干燥,即得到聚酰亚胺粉体,再将聚酰亚胺粉体溶于N-甲基吡咯烷酮(NMP)、二甲基亚砜(DMSO)、N,N-二甲基乙酰胺(DMAc)、N,N-二甲基甲酰胺(DMF)、间甲酚(m-Cresol)或四氢呋喃(THF)中,加热至完全溶解后,将聚酰亚胺纳米复合溶液刮涂在玻璃板上,70~200℃真空干燥去除溶剂,冷却后可取出聚酰亚胺纳米复合膜。
11.根据权利要求1所述的含芴或芴酮结构的聚酰亚胺纳米复合材料,其特征在于其可用于微电子、军工、航空航天、高性能包装与防护以及电子器件封装高新技术产业领域。
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