JPWO2008114798A1 - 多孔性ポリイミド - Google Patents
多孔性ポリイミド Download PDFInfo
- Publication number
- JPWO2008114798A1 JPWO2008114798A1 JP2009505226A JP2009505226A JPWO2008114798A1 JP WO2008114798 A1 JPWO2008114798 A1 JP WO2008114798A1 JP 2009505226 A JP2009505226 A JP 2009505226A JP 2009505226 A JP2009505226 A JP 2009505226A JP WO2008114798 A1 JPWO2008114798 A1 JP WO2008114798A1
- Authority
- JP
- Japan
- Prior art keywords
- bis
- amino
- fluorene
- polyimide
- polyamic acid
- 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
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- 229920001721 polyimide Polymers 0.000 title claims abstract description 123
- 239000004642 Polyimide Substances 0.000 title claims abstract description 113
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 202
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 101
- 229920000592 inorganic polymer Polymers 0.000 claims abstract description 47
- 229920005575 poly(amic acid) Polymers 0.000 claims description 95
- 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 45
- 239000010419 fine particle Substances 0.000 claims description 30
- 125000005370 alkoxysilyl group Chemical group 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 150000004985 diamines Chemical class 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 14
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 187
- -1 bis (3,4-dicarboxyphenyl) sulfone Anhydride Chemical class 0.000 description 133
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 66
- 239000000243 solution Substances 0.000 description 40
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 38
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 23
- 238000000034 method Methods 0.000 description 22
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 19
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 239000000203 mixture Substances 0.000 description 18
- 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 16
- 238000003756 stirring Methods 0.000 description 15
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 13
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 12
- 239000008119 colloidal silica Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 238000005259 measurement Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 125000003277 amino group Chemical group 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 9
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 9
- 239000001110 calcium chloride Substances 0.000 description 9
- 229910001628 calcium chloride Inorganic materials 0.000 description 9
- 230000000704 physical effect Effects 0.000 description 9
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 229920006267 polyester film Polymers 0.000 description 7
- 239000011148 porous material Substances 0.000 description 7
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000006068 polycondensation reaction Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- PAPDRIKTCIYHFI-UHFFFAOYSA-N 4-[3,5-bis(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC(OC=2C=CC(N)=CC=2)=CC(OC=2C=CC(N)=CC=2)=C1 PAPDRIKTCIYHFI-UHFFFAOYSA-N 0.000 description 5
- CNODSORTHKVDEM-UHFFFAOYSA-N 4-trimethoxysilylaniline Chemical compound CO[Si](OC)(OC)C1=CC=C(N)C=C1 CNODSORTHKVDEM-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 230000002194 synthesizing effect Effects 0.000 description 5
- MXPYJVUYLVNEBB-UHFFFAOYSA-N 2-[2-(2-carboxybenzoyl)oxycarbonylbenzoyl]oxycarbonylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1C(O)=O MXPYJVUYLVNEBB-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000004018 acid anhydride group Chemical group 0.000 description 4
- 230000002349 favourable effect Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 3
- APXJLYIVOFARRM-UHFFFAOYSA-N 4-[2-(3,4-dicarboxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(C(O)=O)C(C(O)=O)=C1 APXJLYIVOFARRM-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
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 229910052809 inorganic oxide Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
- RDMFEHLCCOQUMH-UHFFFAOYSA-N 2,4'-Diphenyldiamine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1N RDMFEHLCCOQUMH-UHFFFAOYSA-N 0.000 description 2
- HOLGXWDGCVTMTB-UHFFFAOYSA-N 2-(2-aminophenyl)aniline Chemical group NC1=CC=CC=C1C1=CC=CC=C1N HOLGXWDGCVTMTB-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- CNIQYRSVGUONAA-UHFFFAOYSA-N 2-[4-[9-[4-(2-amino-3-propylphenoxy)phenyl]fluoren-9-yl]phenoxy]-6-propylaniline Chemical compound CCCC1=CC=CC(OC=2C=CC(=CC=2)C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(OC=3C(=C(CCC)C=CC=3)N)=CC=2)=C1N CNIQYRSVGUONAA-UHFFFAOYSA-N 0.000 description 2
- IUCHZABEGFZQOU-UHFFFAOYSA-N 2-[4-[9-[4-(2-amino-5-propylphenoxy)phenyl]fluoren-9-yl]phenoxy]-4-propylaniline Chemical compound CCCC1=CC=C(N)C(OC=2C=CC(=CC=2)C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(OC=3C(=CC=C(CCC)C=3)N)=CC=2)=C1 IUCHZABEGFZQOU-UHFFFAOYSA-N 0.000 description 2
- QWPKWUOJVNPJJB-UHFFFAOYSA-N 2-[4-[9-[4-(2-amino-6-propylphenoxy)phenyl]fluoren-9-yl]phenoxy]-3-propylaniline Chemical compound CCCC1=CC=CC(N)=C1OC1=CC=C(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(OC=3C(=CC=CC=3N)CCC)=CC=2)C=C1 QWPKWUOJVNPJJB-UHFFFAOYSA-N 0.000 description 2
- UWRKLSNNNKRXSF-UHFFFAOYSA-N 3-[2,3-bis(3-aminophenyl)phenyl]aniline Chemical compound NC1=CC=CC(C=2C(=C(C=3C=C(N)C=CC=3)C=CC=2)C=2C=C(N)C=CC=2)=C1 UWRKLSNNNKRXSF-UHFFFAOYSA-N 0.000 description 2
- JLIMOJXOVUKDJX-UHFFFAOYSA-N 3-[methoxy(dimethyl)silyl]aniline Chemical compound CO[Si](C)(C)C1=CC=CC(N)=C1 JLIMOJXOVUKDJX-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 2
- OIYUVHABTRNPAS-UHFFFAOYSA-N 4-[3,4-bis(4-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=C(OC2=C(C=C(C=C2)OC2=CC=C(C=C2)N)OC2=CC=C(C=C2)N)C=C1 OIYUVHABTRNPAS-UHFFFAOYSA-N 0.000 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 description 2
- WNXRUTJHOSVHRR-UHFFFAOYSA-N 4-[4-[9-[4-(4-aminophenoxy)-3,5-dipropylphenyl]fluoren-9-yl]-2,6-dipropylphenoxy]aniline Chemical compound CCCC1=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(CCC)C(OC=3C=CC(N)=CC=3)=C(CCC)C=2)=CC(CCC)=C1OC1=CC=C(N)C=C1 WNXRUTJHOSVHRR-UHFFFAOYSA-N 0.000 description 2
- BQRLVRYTUIZCAX-UHFFFAOYSA-N 4-[4-[9-[4-(4-aminophenoxy)-3-propylphenyl]fluoren-9-yl]-2-propylphenoxy]aniline Chemical compound CCCC1=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(CCC)C(OC=3C=CC(N)=CC=3)=CC=2)=CC=C1OC1=CC=C(N)C=C1 BQRLVRYTUIZCAX-UHFFFAOYSA-N 0.000 description 2
- GBHRFRGWXUDXOE-UHFFFAOYSA-N 4-[[1,3-bis(4-aminophenoxy)-2,4-dihydrotriazin-5-yl]oxy]aniline Chemical compound C1=CC(N)=CC=C1ON1NN(OC=2C=CC(N)=CC=2)C=C(OC=2C=CC(N)=CC=2)C1 GBHRFRGWXUDXOE-UHFFFAOYSA-N 0.000 description 2
- SNLFYGIUTYKKOE-UHFFFAOYSA-N 4-n,4-n-bis(4-aminophenyl)benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1N(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 SNLFYGIUTYKKOE-UHFFFAOYSA-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
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical compound CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- RPHKINMPYFJSCF-UHFFFAOYSA-N benzene-1,3,5-triamine Chemical compound NC1=CC(N)=CC(N)=C1 RPHKINMPYFJSCF-UHFFFAOYSA-N 0.000 description 2
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- HBELKEREKFGFNM-UHFFFAOYSA-N n'-[[4-(2-trimethoxysilylethyl)phenyl]methyl]ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCC1=CC=C(CNCCN)C=C1 HBELKEREKFGFNM-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 125000005372 silanol group Chemical group 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 2
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- FHBXQJDYHHJCIF-UHFFFAOYSA-N (2,3-diaminophenyl)-phenylmethanone Chemical compound NC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N FHBXQJDYHHJCIF-UHFFFAOYSA-N 0.000 description 1
- JPMLZYOQEMXUTO-UHFFFAOYSA-N (ethoxy-methyl-pentan-2-yloxysilyl)formic acid Chemical compound C(CC)C(C)O[Si](OCC)(C(=O)O)C JPMLZYOQEMXUTO-UHFFFAOYSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
- OZHIYEINSCNALY-UHFFFAOYSA-N 1-aminobutan-1-ol Chemical compound CCCC(N)O OZHIYEINSCNALY-UHFFFAOYSA-N 0.000 description 1
- KODLUXHSIZOKTG-UHFFFAOYSA-N 1-aminobutan-2-ol Chemical compound CCC(O)CN KODLUXHSIZOKTG-UHFFFAOYSA-N 0.000 description 1
- DIAVEMFDZKRKMT-UHFFFAOYSA-N 2-(2-triethoxysilylethylsulfanyl)ethanamine Chemical compound CCO[Si](OCC)(OCC)CCSCCN DIAVEMFDZKRKMT-UHFFFAOYSA-N 0.000 description 1
- WOQNVKWPLQDKBF-UHFFFAOYSA-N 2-(2-trimethoxysilylethylsulfanyl)ethanamine Chemical compound CO[Si](OC)(OC)CCSCCN WOQNVKWPLQDKBF-UHFFFAOYSA-N 0.000 description 1
- CRQBUNFZJOLMKC-UHFFFAOYSA-N 2-(3-aminophenyl)aniline Chemical group NC1=CC=CC(C=2C(=CC=CC=2)N)=C1 CRQBUNFZJOLMKC-UHFFFAOYSA-N 0.000 description 1
- VKFRECDXZSYDEC-UHFFFAOYSA-N 2-(4-phenoxyphenoxy)aniline Chemical compound NC1=CC=CC=C1OC(C=C1)=CC=C1OC1=CC=CC=C1 VKFRECDXZSYDEC-UHFFFAOYSA-N 0.000 description 1
- OYJGAVZGTMGAIX-UHFFFAOYSA-N 2-[(2-aminophenoxy)-dimethylsilyl]oxyaniline Chemical compound C=1C=CC=C(N)C=1O[Si](C)(C)OC1=CC=CC=C1N OYJGAVZGTMGAIX-UHFFFAOYSA-N 0.000 description 1
- FYDMBFIJIQPURU-UHFFFAOYSA-N 2-[2-(2-aminophenyl)propan-2-yl]aniline Chemical compound C=1C=CC=C(N)C=1C(C)(C)C1=CC=CC=C1N FYDMBFIJIQPURU-UHFFFAOYSA-N 0.000 description 1
- SULCUXUGHZUJTG-UHFFFAOYSA-N 2-[2-(diethoxymethylsilyl)ethylsulfanyl]ethanamine Chemical compound NCCSCC[SiH2]C(OCC)OCC SULCUXUGHZUJTG-UHFFFAOYSA-N 0.000 description 1
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- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
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- 230000004580 weight loss Effects 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
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- 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
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/26—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a solid phase from a macromolecular composition or article, e.g. leaching out
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- 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
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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
- C08G2101/00—Manufacture of cellular products
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- 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
- C08J2201/00—Foams characterised by the foaming process
- C08J2201/04—Foams characterised by the foaming process characterised by the elimination of a liquid or solid component, e.g. precipitation, leaching out, evaporation
- C08J2201/044—Elimination of an inorganic solid phase
- C08J2201/0442—Elimination of an inorganic solid phase the inorganic phase being a metal, its oxide or hydroxide
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- 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
- C08J2379/00—Characterised by the use 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 C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- Chemical & Material Sciences (AREA)
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- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Abstract
Description
以下に、1)先ず、テトラカルボン酸二無水物と、ジアミン及び/又はトリアミンとを反応せしめてポリアミド酸を合成し、2)次いで、得られたポリアミド酸と、アルコキシシリル基を有するシランカップリング剤とを反応せしめて、複数の末端基のうちの少なくとも一部が水酸基及び/又はアルコキシシリル基であるポリアミド酸を得、3)そして、かかる末端が変性されたポリアミド酸とシリカ微粒子とを用いて、有機−無機ポリマーハイブリッドを合成する手法を詳述する。
9,9−ビス〔4−(4−アミノ−2−メチルフェノキシ)−3,5−ジメチルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−エチルフェノキシ)−3,5−ジメチルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−n−プロピルフェノキシ)−3,5−ジメチルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−i−プロピルフェノキシ)−3,5−ジメチルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−t−ブチルフェノキシ)−3,5−ジメチルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−トリフルオロメチルフェノキシ)−3,5−ジメチルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−メチルフェノキシ)−3,5−ジエチルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−エチルフェノキシ)−3,5−ジエチルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−n−プロピルフェノキシ)−3,5−ジエチルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−i−プロピルフェノキシ)−3,5−ジエチルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−t−ブチルフェノキシ)−3,5−ジエチルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−トリフルオロメチルフェノキシ)−3,5−ジエチルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−メチルフェノキシ)−3,5−ジ−n−プロピルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−エチルフェノキシ)−3,5−ジ−n−プロピルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−n−プロピルフェノキシ)−3,5−ジ−n−プロピルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−i−プロピルフェノキシ)−3,5−ジ−n−プロピルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−t−ブチルフェノキシ)−3,5−ジ−n−プロピルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−トリフルオロメチルフェノキシ)−3,5−ジ−n−プロピルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−メチルフェノキシ)−3,5−ジ−i−プロピルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−エチルフェノキシ)−3,5−ジ−i−プロピルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−n−プロピルフェノキシ)−3,5−ジ−i−プロピルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−i−プロピルフェノキシ)−3,5−ジ−i−プロピルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−t−ブチルフェノキシ)−3,5−ジ−i−プロピルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−トリフルオロメチルフェノキシ)−3,5−ジ−i−プロピルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−メチルフェノキシ)−3,5−ジ−t−ブチルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−エチルフェノキシ)−3,5−ジ−t−ブチルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−n−プロピルフェノキシ)−3,5−ジ−t−ブチルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−i−プロピルフェノキシ)−3,5−ジ−t−ブチルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−t−ブチルフェノキシ)−3,5−ジ−t−ブチルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−トリフルオロメチルフェノキシ)−3,5−ジ−t−ブチルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−メチルフェノキシ)−3,5−ジ(トリフルオロメチル)フェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−エチルフェノキシ)−3,5−ジ(トリフルオロメチル)フェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−n−プロピルフェノキシ)−3,5−ジ(トリフルオロメチル)フェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−i−プロピルフェノキシ)−3,5−ジ(トリフルオロメチル)フェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−t−ブチルフェノキシ)−3,5−ジ(トリフルオロメチル)フェニル〕フルオレン、9,9−ビス〔4−(4−アミノ−2−トリフルオロメチルフェノキシ)−3,5−ジ(トリフルオロメチル)フェニル〕フルオレン、9,9−ビス〔4−(2−アミノ−3−メチルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(2−アミノ−4−メチルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(2−アミノ−5−メチルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(2−アミノ−6−メチルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(2−アミノ−3−トリフロオロメチルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(2−アミノ−4−トリフロオロメチルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(2−アミノ−5−トリフロオロメチルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(2−アミノ−6−トリフロオロメチルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(3−アミノ−2−メチルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(3−アミノ−4−メチルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(3−アミノ−5−メチルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(3−アミノ−6−メチルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(3−アミノ−2−エチルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(3−アミノ−4−エチルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(3−アミノ−5−エチルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(3−アミノ−6−エチルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(3−アミノ−2−n−プロピルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(3−アミノ−4−n−プロピルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(3−アミノ−5−n−プロピルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(3−アミノ−6−n−プロピルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(3−アミノ−2−i−プロピルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(3−アミノ−4−i−プロピルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(3−アミノ−5−i−プロピルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(3−アミノ−6−i−プロピルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(3−アミノ−2−t−ブチルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(3−アミノ−4−t−ブチルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(3−アミノ−5−t−ブチルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(3−アミノ−6−t−ブチルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(3−アミノ−2−トリフロオロメチルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(3−アミノ−4−トリフロオロメチルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(3−アミノ−5−トリフロオロメチルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(3−アミノ−6−トリフロオロメチルフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノフェノキシ)−3−メチルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノフェノキシ)−3−エチルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノフェノキシ)−3−n−プロピルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノフェノキシ)−3−i−プロピルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノフェノキシ)−3−t−ブチルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノフェノキシ)−3−トリフルオロメチルフェニル〕フルオレン、9−ビス〔4−(4−アミノフェノキシ)−3,5−ジメチルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノフェノキシ)−3,5−ジエチルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノフェノキシ)−3,5−ジ−n−プロピルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノフェノキシ)−3,5−ジ−i−プロピルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノフェノキシ)−3,5−ジ−t−ブチルフェニル〕フルオレン、9,9−ビス〔4−(4−アミノフェノキシ)−3,5−ジ(トリフルオロメチル)フェニル〕フルオレン、m−フェニレンジアミン、p−フェニレンジアミノン、2,2′−ジアミノビフェニル、2,3′−ジアミノビフェニル、2,4′−ジアミノビフェニル、3,3′−ジアミノビフェニル、3,4′−ジアミノビフェニル、4,4′−ジアミノビフェニル、2−(3−アミノフェニル)−3′−アミノビフェニル、2,2′−ビス(3−アミノフェニル)ビフェニル、2,2′−ジアミノジフェニルエーテル、2,3′−ジアミノジフェニルエーテル、2,4′−ジアミノジフェニルエーテル、3,3′−ジアミノジフェニルエーテル、3,4′−ジアミノジフェニルエーテル、4,4′−ジアミノジフェニルエーテル、2,2−ビス(2−アミノフェニル)プロパン、2,2−ビス(3−アミノフェニル)プロパン、2,2−ビス(4−アミノフェニル)プロパン、2,2−ビス〔3−(2−アミノフェノキシ)フェニル〕プロパン、2,2−ビス〔3−(3−アミノフェノキシ)フェニル〕プロパン、2,2−ビス〔4−(2−アミノフェノキシ)フェニル〕プロパン、2,2−ビス〔4−(3−アミノフェノキシ)フェニル〕プロパン、2,2−ビス〔4−(4−アミノフェノキシ)フェニル〕プロパン等の芳香族ジアミンを例示することが出来る。また、本発明においては、4,4’−メチレンビス(シクロヘキシルアミン)、イソホロンジアミン、シス−1,4−ジアミノシクロヘキサン、1,4−シクロヘキサンビス(メチルアミン)、2,5−ビス(アミノメチル)ビシクロ〔2.2.1〕ヘプタン、2,6−ビス(アミノメチル)ビシクロ〔2.2.1〕ヘプタン、3,8−ビス(アミノメチル)トリシクロ〔5.2.1.0〕デカン、1,3−ジアミノアダマンタン、2,2−ビス(4−アミノシクロヘキシル)プロパン、2,2−ビス(4−アミノシクロヘキシル)ヘキサフルオロプロパン、1,3−プロパンジアミン、1,4−テトラメチレンジアミン、1,5−ペンタメチレンジアミン、1,6−ヘキサメチレンジアミン、1,7−ヘプタメチレンジアミン、1,8−オクタメチレンジアミン、1,9−ノナメチレンジアミン、ビス(4−アミノシクロヘキシル)メタン、ビス(4−アミノ−3−メチルシクロヘキシル)メタン等の脂肪族ジアミンも、使用可能である。
かかる手法においても、先ず、ポリアミド酸が合成されることとなる。なお、かかるポリアミド酸の合成に際して用いられ得るテトラカルボン酸二無水物及びトリアミンは、上述したa)の有機−無機ポリマーハイブリッドの合成手法において用いられ得るものと同様である。また、使用可能なジアミン及びトリアミン、シロキサンジアミンや分子内にアミノ基を4個以上有するアミン化合物を併用し得ること、及び合成の際の条件等も、上述の如きa)の合成手法と同様である。
R1 mSi(OR2)n・・・式(1)
R1 、R2 :炭化水素基
m:0又は正の整数
n:正の整数
但し、m+n=4
得られたフィルムについて、HF水溶液に浸漬する前後での重量及び体積の変化より、算出した。
得られたフィルムについて、空気雰囲気下、昇温速度:10℃/minの条件にて熱重量測定(TG−DTA)を行ない、得られたTG曲線から、熱分解温度(5%重量減少温度:Td 5[℃])を求めた。
得られたフィルムについて、窒素気流下、昇温速度:5℃/minの条件にて熱機械測定(TMA)を行ない、得られたTMA曲線の100〜150℃間における伸張度から、線熱膨張係数(CTE[ppm/℃])を求めた。
紫外−可視光透過率測定により、600nmにおける光透過率[%]を求めた。
得られたフィルムについて、室温下、引張速度:5mm/minの条件にて引張強度試験を行ない、得られた応力−歪み曲線から、伸び率(ε[%])、引張強度(σ[MPa])及びヤング率(E[GPa])を求めた。
得られたフィルムについて、周波数範囲:100kHz、測定温度:25℃の条件にて測定した。なお、測定に際しては、試料として、得られたフィルムの両面に銀ペーストを塗布して、電極処理を施したものを用いた。
攪拌機、窒素導入管、塩化カルシウム管及び温度計を備えた100mLの三つロフラスコに、N−Nジメチルアセトアミド(DMAc):40mLを加え,4,4’−(ヘキサフロロイソプロピリデン)ジフタル酸二無水物(6FDA):1.3g(3mmol)を溶解させた。この溶液を、窒素気流下に攪拌しながら、20mLのDMAcに予め溶解させた1,3,5−トリス(4−アミノフェノキシ)ベンゼン(TAPOB):0.64g(1.6mmol)を徐々に加えた後、更に25℃で3時間、攪拌した。その後、3−アミノプロピルトリメトキシシラン(APTrMOS):0.07g(0.4mmol)を加え、1時間撹拌し、シラン末端多分岐ポリアミド酸を合成した。
芳香族テトラカルボン酸二無水物として、無水ピロメリット酸(PMDA):0.65g(3mmol)を使用し、DMAc分散コロイダルシリカの使用量を変更した以外は実験例1と同様にして、6種類のフィルム(実施例2a〜2f)を得た。得られた6種類のフィルムも、FT−IR測定から、多分岐ポリイミドフィルムであることが認められた。また、各フィルムは、薄黄色を呈するものの、何れも良好な透明性を有するものであった。各フィルムについて測定した物性を、下記表1に示す。更に、空孔率が7%であったフィルム(実施例2b)についてのTEM写真を、図2に示す。
攪拌機、窒素導入管、塩化カルシウム管及び温度計を備えた100mLの三つロフラスコに、N−Nメチルアセトアミド(DMAc):40mLを加え,4,4’−(ヘキサフロロイソプロピリデン)ジフタル酸二無水物(6FDA):1.3g(3mmol)を溶解させた。この溶液を、窒素気流下に攪拌しながら、20mLのDMAcに予め溶解させた1,3,5−トリス(4−アミノフェノキシ)ベンゼン(TAPOB):0.64g(1.6mmol)を徐々に加えた後、更に25℃で3時間、攪拌した。その後、3−アミノプロピルトリメトキシシラン(APTrMOS):0.07g(0.4mmol)を加え、1時間撹拌し、シラン末端多分岐ポリアミド酸を合成した。
攪拌機、窒素導入管、塩化カルシウム管及び温度計を備えた100mLの三つロフラスコに、N−メチル−2−ピロリドン(NMP):20mLを加え,1,3−ビス(4−アミノフェノキシ)ベンゼン(TPER):2.2g(7.5mmol)を溶解させた。この溶液を、窒素気流下に攪拌しながら、7mlのNMPに溶解させた4,4’−(ヘキサフロロイソプロピリデン)ジフタル酸二無水物(6FDA):3.2g(7.3mmol)を徐々に加えた後、さらに25℃で3時間攪拌し、アミン末端直鎖ポリアミド酸を合成した。
先ず、芳香族テトラカルボン酸二無水物として無水ピロメリット酸(PMDA):1.59g(7.3mmol)を使用した以外は実施例4a〜4dと同様にして、アミン末端直鎖ポリアミド酸を合成した。
攪拌機、窒素導入管、塩化カルシウム管及び温度計を備えた100mLの三つロフラスコに、N−メチル−2−ピロリドン(NMP):20mLを加え,無水ピロメリット酸(PMDA):3.3g(15.2mmol)を溶解させた。この溶液を、窒素気流下に攪拌しながら、10mLのNMPに溶解させたオキシジアニリン(ODA):2.9g(14.7mmol)を徐々に加えた後、さらに25℃で3時間、攪拌し、酸無水物末端直鎖ポリアミド酸を合成した。
先ず、芳香族テトラカルボン酸二無水物として、4,4’−(ヘキサフロロイソプロピリデン)ジフタル酸二無水物(6FDA):6.7g(15.2mmol)を使用した以外は、実施例5a〜5dと同様にして、酸無水物末端直鎖ポリイミド酸を合成した。
攪拌機、窒素導入管、塩化カルシウム管および温度計を備えた100mLの三つロフラスコに、N−Nジメチルアセトアミド(DMAC):10mLを加え、無水ピロメリット酸(PMDA):0.65g(3mmol)を溶解させた。この溶液を、窒素気流下に攪拌しながら、1,3−ビス(4−アミノフェノキシ)ベンゼン(TPER):0.8g(2.75mmol)及びDMAC:10mLを加えた後、更に25℃で3時間、攪拌し、酸無水物末端直鎖ポリアミド酸を合成した。この溶液に、3−アミノプロピルトリメトキシシラン(APTrMOS):0.09g(0.5mmol)を加え、1時間撹拌し、シラン末端直鎖ポリアミド酸を合成した。
攪拌機、窒素導入管、塩化カルシウム管および温度計を備えた100mLの三つロフラスコに、N−Nジメチルアセトアミド(DMAc):10mLを加え、無水ピロメリット酸(PMDA):0.62g(3mmol)を溶解させた。この溶液を、窒素気流下に攪拌しながら、オキシジアニリン(ODA):0.55g(2.75mmol)及びDMAc:10mLを加えた後、さらに25℃で3時間、攪拌し、酸無水物末端直鎖ポリアミド酸を合成した。この溶液に、3−アミノプロピルトリメトキシシラン(APTrMOS):0.09g(0.5mmol)を加え、1時間撹拌し、シラン末端直鎖ポリアミド酸を合成した。
攪拌機、窒素導入管、塩化カルシウム管及び温度計を備えた100mLの三つロフラスコに、N−Nジメチルアセトアミド(DMAc):40mLを加え、4,4’−(ヘキサフロロイソプロピリデン)ジフタル酸二無水物(6FDA):1.3g(3mmol)を溶解させた。この溶液を、窒素気流下に攪拌しながら、DMAc:20mLに予め溶解させた1,3,5−トリス(4−アミノフェノキシ)ベンゼン(TAPOB):0.64g(3mmol)を徐々に加えた後、さらに25℃で3時間、攪拌し、酸無水物末端多分岐ポリアミド酸を合成した。得られた酸無水物末端多分岐ポリアミド酸のDMAc溶液に、任意量のDMAc分散コロイダルシリカを滴下し、激しく攪拌した後に、ポリエステルフイルム上にキャストし、85℃で2時間、乾燥し、多分岐ポリアミド酸とコロイダルシリカとの混合物からなるフィルムを調製した。DMAc分散コロイダルシリカの滴下量を適宜、変化させることにより、シリカ含有量が異なる5種類のフィルム(比較例10a:約0重量%、比較例10b:約10重量%、比較例10c:約20重量%、比較例10d:約30重量%、比較例10e:約40重量%)を調製した。各フィルムを、窒素雰囲気下に、100℃で1時間、200℃で1時間、更に300℃で1時間、加熱処理し、多分岐ポリイミドとコロイダルシリカの混合物からなるフィルムを5種類、得た。
Claims (8)
- ポリイミド相とシリカ相とが共有結合によって一体となった分子構造を呈する有機−無機ポリマーハイブリッドに対して、該シリカ相の除去処理を施して得られる多孔性ポリイミド。
- 前記ポリイミド相が、少なくともその一部にデンドリティック構造を有するものである請求項1に記載の多孔性ポリイミド。
- 前記有機−無機ポリマーハイブリッドが、複数の末端基のうちの少なくとも一部が水酸基及び/又はアルコキシシリル基であるポリアミド酸と、前記シリカ相に相当するシリカ微粒子とが共有結合によって一体となったポリアミド酸−シリカハイブリッドを、イミド化せしめたものである請求項1又は請求項2に記載の多孔性ポリイミド。
- 前記ポリアミド酸が、テトラカルボン酸二無水物と、ジアミン及び/又はトリアミンと、アルコキシシリル基を有するシランカップリング剤とを反応せしめて得られたものである請求項3に記載の多孔性ポリイミド。
- 前記有機−無機ポリマーハイブリッドが、複数の末端基のうちの少なくとも一部が水酸基及び/又はアルコキシシリル基であるポリアミド酸と、アルコキシシラン化合物とを、水の存在下、ゾル−ゲル反応せしめ、得られた反応生成物をイミド化せしめてなるものである請求項1又は請求項2に記載の多孔性ポリイミド。
- 前記有機−無機ポリマーハイブリッドが、複数の末端基のうちの少なくとも一部が水酸基及び/又はアルコキシシリル基であるポリアミド酸を、イミド化せしめてポリイミドとし、かかるポリイミドとアルコキシシラン化合物とを、水の存在下、ゾル−ゲル反応せしめて得られるものである請求項1又は請求項2に記載の多孔性ポリイミド。
- 前記ポリアミド酸が、テトラカルボン酸二無水物と、ジアミン及び/又はトリアミンと、アルコキシシリル基を有するシランカップリング剤とを反応せしめて得られたものである請求項5又は請求項6に記載の多孔性ポリイミド。
- 請求項1乃至請求項7の何れか1項に記載の多孔性ポリイミドよりなるポリイミドフィルム。
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