WO2021201228A1 - 樹脂、樹脂前駆体組成物、塗液組成物、電子写真感光体、成形物、電子デバイス、および電子写真感光体の製造方法 - Google Patents
樹脂、樹脂前駆体組成物、塗液組成物、電子写真感光体、成形物、電子デバイス、および電子写真感光体の製造方法 Download PDFInfo
- Publication number
- WO2021201228A1 WO2021201228A1 PCT/JP2021/014164 JP2021014164W WO2021201228A1 WO 2021201228 A1 WO2021201228 A1 WO 2021201228A1 JP 2021014164 W JP2021014164 W JP 2021014164W WO 2021201228 A1 WO2021201228 A1 WO 2021201228A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polymer
- carbon atoms
- conjugated diene
- group
- resin
- Prior art date
Links
- 229920005989 resin Polymers 0.000 title claims abstract description 245
- 239000011347 resin Substances 0.000 title claims abstract description 245
- 239000000203 mixture Substances 0.000 title claims description 164
- 239000002243 precursor Substances 0.000 title claims description 58
- 238000004519 manufacturing process Methods 0.000 title claims description 45
- 239000008199 coating composition Substances 0.000 title claims description 16
- 108091008695 photoreceptors Proteins 0.000 title 2
- 229920000642 polymer Polymers 0.000 claims abstract description 462
- 239000004417 polycarbonate Substances 0.000 claims abstract description 138
- 125000003118 aryl group Chemical group 0.000 claims abstract description 45
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 45
- 238000005698 Diels-Alder reaction Methods 0.000 claims abstract description 32
- 229920001230 polyarylate Polymers 0.000 claims abstract description 16
- 125000002897 diene group Chemical group 0.000 claims description 179
- 125000004432 carbon atom Chemical group C* 0.000 claims description 143
- 238000006243 chemical reaction Methods 0.000 claims description 84
- 238000004132 cross linking Methods 0.000 claims description 66
- 238000000034 method Methods 0.000 claims description 52
- 239000011248 coating agent Substances 0.000 claims description 49
- 238000000576 coating method Methods 0.000 claims description 49
- 239000007788 liquid Substances 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 42
- 239000003960 organic solvent Substances 0.000 claims description 27
- 125000001931 aliphatic group Chemical group 0.000 claims description 25
- 238000010438 heat treatment Methods 0.000 claims description 20
- 239000000758 substrate Substances 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000005647 linker group Chemical group 0.000 claims description 15
- 238000000465 moulding Methods 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000004122 cyclic group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 9
- 230000001588 bifunctional effect Effects 0.000 claims description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052710 silicon Inorganic materials 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 5
- 150000001349 alkyl fluorides Chemical class 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000004437 phosphorous atom Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 181
- 239000010410 layer Substances 0.000 description 104
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 65
- -1 maleimide compound Chemical class 0.000 description 58
- 239000000243 solution Substances 0.000 description 56
- 239000000126 substance Substances 0.000 description 52
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 51
- 239000002904 solvent Substances 0.000 description 43
- 230000015572 biosynthetic process Effects 0.000 description 33
- 238000003786 synthesis reaction Methods 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 150000001993 dienes Chemical class 0.000 description 30
- 239000011230 binding agent Substances 0.000 description 29
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 28
- 238000003756 stirring Methods 0.000 description 26
- 239000000463 material Substances 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 229910052731 fluorine Inorganic materials 0.000 description 24
- 239000007864 aqueous solution Substances 0.000 description 22
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000011737 fluorine Substances 0.000 description 21
- 239000000049 pigment Substances 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 20
- 239000000523 sample Substances 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- WUGKVYDVIGOPSI-UHFFFAOYSA-N 4-(4-hydroxy-3-methylphenyl)-2-methylphenol Chemical group C1=C(O)C(C)=CC(C=2C=C(C)C(O)=CC=2)=C1 WUGKVYDVIGOPSI-UHFFFAOYSA-N 0.000 description 17
- 239000003963 antioxidant agent Substances 0.000 description 17
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 16
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- 239000000975 dye Substances 0.000 description 15
- 238000005259 measurement Methods 0.000 description 15
- 230000000694 effects Effects 0.000 description 14
- SJHHDDDGXWOYOE-UHFFFAOYSA-N oxytitamium phthalocyanine Chemical compound [Ti+2]=O.C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 SJHHDDDGXWOYOE-UHFFFAOYSA-N 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 230000003078 antioxidant effect Effects 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 239000000539 dimer Substances 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 11
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 230000006866 deterioration Effects 0.000 description 11
- 125000000524 functional group Chemical group 0.000 description 11
- 229920005668 polycarbonate resin Polymers 0.000 description 11
- 239000004431 polycarbonate resin Substances 0.000 description 11
- 238000005299 abrasion Methods 0.000 description 10
- 125000005577 anthracene group Chemical group 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- YEKWCXNXBLQUTF-UHFFFAOYSA-N 4-[[10-(4-hydroxyphenyl)anthracen-9-yl]methyl]phenol Chemical compound C1=CC(O)=CC=C1CC(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(O)C=C1 YEKWCXNXBLQUTF-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000003999 initiator Substances 0.000 description 9
- 239000000178 monomer Substances 0.000 description 9
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 9
- 230000000704 physical effect Effects 0.000 description 9
- 229920000728 polyester Polymers 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 230000008859 change Effects 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 229920003192 poly(bis maleimide) Polymers 0.000 description 8
- 239000011241 protective layer Substances 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 230000000903 blocking effect Effects 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 125000001153 fluoro group Chemical group F* 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 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 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- 239000011669 selenium Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 5
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 5
- 239000005695 Ammonium acetate Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 238000007605 air drying Methods 0.000 description 5
- 229940043376 ammonium acetate Drugs 0.000 description 5
- 235000019257 ammonium acetate Nutrition 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 230000006837 decompression Effects 0.000 description 5
- 238000010894 electron beam technology Methods 0.000 description 5
- 230000005284 excitation Effects 0.000 description 5
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- HTVITOHKHWFJKO-UHFFFAOYSA-N Bisphenol B Chemical compound C=1C=C(O)C=CC=1C(C)(CC)C1=CC=C(O)C=C1 HTVITOHKHWFJKO-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 108010078791 Carrier Proteins Proteins 0.000 description 4
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 4
- 238000012696 Interfacial polycondensation Methods 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000006085 branching agent Substances 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000010526 radical polymerization reaction Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229910052711 selenium Inorganic materials 0.000 description 4
- 150000003384 small molecules Chemical class 0.000 description 4
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical class [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 4
- 230000008961 swelling Effects 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
- IPJGAEWUPXWFPL-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(N2C(C=CC2=O)=O)=C1 IPJGAEWUPXWFPL-UHFFFAOYSA-N 0.000 description 3
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 3
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- 0 C**C=C(*C1IC1)N*1=*C*C(C)C=*1 Chemical compound C**C=C(*C1IC1)N*1=*C*C(C)C=*1 0.000 description 3
- 101000972449 Homo sapiens Sperm-egg fusion protein LLCFC1 Proteins 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000000020 Nitrocellulose Substances 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 238000006742 Retro-Diels-Alder reaction Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 102100022736 Sperm-egg fusion protein LLCFC1 Human genes 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 229920000180 alkyd Polymers 0.000 description 3
- FNGGVJIEWDRLFV-UHFFFAOYSA-N anthracene-1,2-dicarboxylic acid Chemical group C1=CC=CC2=CC3=C(C(O)=O)C(C(=O)O)=CC=C3C=C21 FNGGVJIEWDRLFV-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000007809 chemical reaction catalyst Substances 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000010419 fine particle Substances 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- 230000001771 impaired effect Effects 0.000 description 3
- 229910003437 indium oxide Inorganic materials 0.000 description 3
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 3
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229920001220 nitrocellulos Polymers 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- 239000005011 phenolic resin Substances 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 229920001721 polyimide Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000000565 sealant Substances 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 3
- 125000005259 triarylamine group Chemical group 0.000 description 3
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 2
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 2
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- BLLFPKZTBLMEFG-UHFFFAOYSA-N 1-(4-hydroxyphenyl)pyrrole-2,5-dione Chemical compound C1=CC(O)=CC=C1N1C(=O)C=CC1=O BLLFPKZTBLMEFG-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- OGRAOKJKVGDSFR-UHFFFAOYSA-N 2,3,5-trimethylphenol Chemical compound CC1=CC(C)=C(C)C(O)=C1 OGRAOKJKVGDSFR-UHFFFAOYSA-N 0.000 description 2
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 description 2
- XILYZMFMZQXKMC-UHFFFAOYSA-N 2-(furan-2-ylmethyl)benzene-1,4-diol Chemical compound OC1=CC=C(O)C(CC=2OC=CC=2)=C1 XILYZMFMZQXKMC-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 2
- QDBOAKPEXMMQFO-UHFFFAOYSA-N 4-(4-carbonochloridoylphenyl)benzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=C(C(Cl)=O)C=C1 QDBOAKPEXMMQFO-UHFFFAOYSA-N 0.000 description 2
- XDGXPHFWSPGAIB-UHFFFAOYSA-N 4-[1-(4-hydroxy-3-methylphenyl)ethyl]-2-methylphenol Chemical compound C=1C=C(O)C(C)=CC=1C(C)C1=CC=C(O)C(C)=C1 XDGXPHFWSPGAIB-UHFFFAOYSA-N 0.000 description 2
- YWKDIAQEJCJKHU-UHFFFAOYSA-N 4-anthracen-9-ylphenol Chemical compound C1=CC(O)=CC=C1C1=C(C=CC=C2)C2=CC2=CC=CC=C12 YWKDIAQEJCJKHU-UHFFFAOYSA-N 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
- 102100032533 ADP/ATP translocase 1 Human genes 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 101000768061 Escherichia phage P1 Antirepressor protein 1 Proteins 0.000 description 2
- 239000001856 Ethyl cellulose Substances 0.000 description 2
- 101000796932 Homo sapiens ADP/ATP translocase 1 Proteins 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
- 239000004640 Melamine resin Substances 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-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
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920002396 Polyurea Polymers 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000012790 adhesive layer Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229920003232 aliphatic polyester Polymers 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- QSYYLCHYRULSFV-UHFFFAOYSA-N anthracene-1,4-diol Chemical compound C1=CC=C2C=C3C(O)=CC=C(O)C3=CC2=C1 QSYYLCHYRULSFV-UHFFFAOYSA-N 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 2
- 235000021240 caseins Nutrition 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 description 2
- 229960004419 dimethyl fumarate Drugs 0.000 description 2
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 2
- 229960001826 dimethylphthalate Drugs 0.000 description 2
- 239000008393 encapsulating agent Substances 0.000 description 2
- 229920001249 ethyl cellulose Polymers 0.000 description 2
- 235000019325 ethyl cellulose Nutrition 0.000 description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000012678 infectious agent Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000004957 naphthylene group Chemical group 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 229920006122 polyamide resin Polymers 0.000 description 2
- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 229920001195 polyisoprene Polymers 0.000 description 2
- 229920001470 polyketone Polymers 0.000 description 2
- 230000037048 polymerization activity Effects 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 229920005749 polyurethane resin Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 2
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 125000005504 styryl group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 229910001887 tin oxide Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- 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 1
- ZYMCBJWUWHHVRX-UHFFFAOYSA-N (4-nitrophenyl)-phenylmethanone Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)C1=CC=CC=C1 ZYMCBJWUWHHVRX-UHFFFAOYSA-N 0.000 description 1
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical class O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 description 1
- DMDPKUWXJUYFKO-UHFFFAOYSA-N 1,1'-biphenyl;hydrochloride Chemical compound Cl.C1=CC=CC=C1C1=CC=CC=C1 DMDPKUWXJUYFKO-UHFFFAOYSA-N 0.000 description 1
- QVLAWKAXOMEXPM-UHFFFAOYSA-N 1,1,1,2-tetrachloroethane Chemical compound ClCC(Cl)(Cl)Cl QVLAWKAXOMEXPM-UHFFFAOYSA-N 0.000 description 1
- KEKQWCLOVHSOCU-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-pentacosafluorododecyl 4-hydroxybenzoate Chemical compound OC1=CC=C(C(=O)OC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C=C1 KEKQWCLOVHSOCU-UHFFFAOYSA-N 0.000 description 1
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical compound FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- UTCOUOISVRSLSH-UHFFFAOYSA-N 1,2-Anthracenediol Chemical compound C1=CC=CC2=CC3=C(O)C(O)=CC=C3C=C21 UTCOUOISVRSLSH-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- NMNSBFYYVHREEE-UHFFFAOYSA-N 1,2-dinitroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C([N+]([O-])=O)C([N+](=O)[O-])=CC=C3C(=O)C2=C1 NMNSBFYYVHREEE-UHFFFAOYSA-N 0.000 description 1
- IZUKQUVSCNEFMJ-UHFFFAOYSA-N 1,2-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1[N+]([O-])=O IZUKQUVSCNEFMJ-UHFFFAOYSA-N 0.000 description 1
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 1
- XVMIKRZPDSXBTP-UHFFFAOYSA-N 1,3-dibromobutan-2-one Chemical compound CC(Br)C(=O)CBr XVMIKRZPDSXBTP-UHFFFAOYSA-N 0.000 description 1
- WDCYWAQPCXBPJA-UHFFFAOYSA-N 1,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC([N+]([O-])=O)=C1 WDCYWAQPCXBPJA-UHFFFAOYSA-N 0.000 description 1
- XAZPKEBWNIUCKF-UHFFFAOYSA-N 1-[4-[4-[2-[4-[4-(2,5-dioxopyrrol-1-yl)phenoxy]phenyl]propan-2-yl]phenoxy]phenyl]pyrrole-2,5-dione Chemical compound C=1C=C(OC=2C=CC(=CC=2)N2C(C=CC2=O)=O)C=CC=1C(C)(C)C(C=C1)=CC=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O XAZPKEBWNIUCKF-UHFFFAOYSA-N 0.000 description 1
- CCFAKBRKTKVJPO-UHFFFAOYSA-N 1-anthroic acid Chemical compound C1=CC=C2C=C3C(C(=O)O)=CC=CC3=CC2=C1 CCFAKBRKTKVJPO-UHFFFAOYSA-N 0.000 description 1
- MUVQKFGNPGZBII-UHFFFAOYSA-N 1-anthrol Chemical compound C1=CC=C2C=C3C(O)=CC=CC3=CC2=C1 MUVQKFGNPGZBII-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- HJRJRUMKQCMYDL-UHFFFAOYSA-N 1-chloro-2,4,6-trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(Cl)C([N+]([O-])=O)=C1 HJRJRUMKQCMYDL-UHFFFAOYSA-N 0.000 description 1
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical group CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- HOQAPVYOGBLGOC-UHFFFAOYSA-N 1-ethyl-9h-carbazole Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2CC HOQAPVYOGBLGOC-UHFFFAOYSA-N 0.000 description 1
- 125000006039 1-hexenyl group Chemical group 0.000 description 1
- PTXVSDKCUJCCLC-UHFFFAOYSA-N 1-hydroxyindole Chemical compound C1=CC=C2N(O)C=CC2=C1 PTXVSDKCUJCCLC-UHFFFAOYSA-N 0.000 description 1
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- LWHDQPLUIFIFFT-UHFFFAOYSA-N 2,3,5,6-tetrabromocyclohexa-2,5-diene-1,4-dione Chemical group BrC1=C(Br)C(=O)C(Br)=C(Br)C1=O LWHDQPLUIFIFFT-UHFFFAOYSA-N 0.000 description 1
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 1
- USAYMJGCALIGIG-UHFFFAOYSA-N 2,3-dichlorocyclohexa-2,5-diene-1,4-dione Chemical compound ClC1=C(Cl)C(=O)C=CC1=O USAYMJGCALIGIG-UHFFFAOYSA-N 0.000 description 1
- QBDAFARLDLCWAT-UHFFFAOYSA-N 2,3-dihydropyran-6-one Chemical compound O=C1OCCC=C1 QBDAFARLDLCWAT-UHFFFAOYSA-N 0.000 description 1
- JOERSAVCLPYNIZ-UHFFFAOYSA-N 2,4,5,7-tetranitrofluoren-9-one Chemical compound O=C1C2=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C2C2=C1C=C([N+](=O)[O-])C=C2[N+]([O-])=O JOERSAVCLPYNIZ-UHFFFAOYSA-N 0.000 description 1
- VHQGURIJMFPBKS-UHFFFAOYSA-N 2,4,7-trinitrofluoren-9-one Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C2C3=CC=C([N+](=O)[O-])C=C3C(=O)C2=C1 VHQGURIJMFPBKS-UHFFFAOYSA-N 0.000 description 1
- MAQOZOILPAMFSW-UHFFFAOYSA-N 2,6-bis[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=C(CC=3C(=CC=C(C)C=3)O)C=C(C)C=2)O)=C1 MAQOZOILPAMFSW-UHFFFAOYSA-N 0.000 description 1
- HDVGAFBXTXDYIB-UHFFFAOYSA-N 2,7-dinitrofluoren-9-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)C3=CC([N+](=O)[O-])=CC=C3C2=C1 HDVGAFBXTXDYIB-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- QBTHTNCUNBHSHN-UHFFFAOYSA-N 2-[3,5-bis(2-hydroxyphenyl)phenyl]phenol Chemical compound OC1=CC=CC=C1C1=CC(C=2C(=CC=CC=2)O)=CC(C=2C(=CC=CC=2)O)=C1 QBTHTNCUNBHSHN-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 1
- YJERZJLSXBRUDQ-UHFFFAOYSA-N 2-o-(3,4-dihydroxybutyl) 1-o-methyl benzene-1,2-dicarboxylate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OCCC(O)CO YJERZJLSXBRUDQ-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 236TMPh Natural products CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 1
- GEKJEMDSKURVLI-UHFFFAOYSA-N 3,4-dibromofuran-2,5-dione Chemical compound BrC1=C(Br)C(=O)OC1=O GEKJEMDSKURVLI-UHFFFAOYSA-N 0.000 description 1
- VYWYYJYRVSBHJQ-UHFFFAOYSA-N 3,5-dinitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 VYWYYJYRVSBHJQ-UHFFFAOYSA-N 0.000 description 1
- LWFUFLREGJMOIZ-UHFFFAOYSA-N 3,5-dinitrosalicylic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O LWFUFLREGJMOIZ-UHFFFAOYSA-N 0.000 description 1
- MOSSLXZUUKTULI-UHFFFAOYSA-N 3-[3-(2,5-dioxopyrrol-3-yl)-4-methylphenyl]pyrrole-2,5-dione Chemical compound CC1=CC=C(C=2C(NC(=O)C=2)=O)C=C1C1=CC(=O)NC1=O MOSSLXZUUKTULI-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- CSEXLCUTMMBMDZ-UHFFFAOYSA-N 4-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)phenol Chemical compound OC1=CC=C(C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C=C1 CSEXLCUTMMBMDZ-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- KNDMSTHPPVVZAB-UHFFFAOYSA-N 4-[10-(4-hydroxy-3-methylphenyl)anthracen-9-yl]-2-methylphenol Chemical compound CC=1C=C(C=CC=1O)C=1C2=CC=CC=C2C(=C2C=CC=CC=12)C1=CC(=C(C=C1)O)C KNDMSTHPPVVZAB-UHFFFAOYSA-N 0.000 description 1
- OPKQAOBTBQLNCB-UHFFFAOYSA-N 4-[10-(4-hydroxyphenyl)anthracen-9-yl]phenol Chemical compound C1=CC(O)=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=C(O)C=C1 OPKQAOBTBQLNCB-UHFFFAOYSA-N 0.000 description 1
- NEOADHINJHPAQK-UHFFFAOYSA-N 4-[2,6-bis(4-hydroxyphenyl)-2,6-dimethylhept-3-en-4-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)CC(C=1C=CC(O)=CC=1)=CC(C)(C)C1=CC=C(O)C=C1 NEOADHINJHPAQK-UHFFFAOYSA-N 0.000 description 1
- XJGTVJRTDRARGO-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)propan-2-yl]benzene-1,3-diol Chemical compound C=1C=C(O)C=C(O)C=1C(C)(C)C1=CC=C(O)C=C1 XJGTVJRTDRARGO-UHFFFAOYSA-N 0.000 description 1
- JHSDIILQGDBNPD-UHFFFAOYSA-N 4-[2-[4-[tris[4-[2-(4-hydroxyphenyl)propan-2-yl]phenoxy]methoxy]phenyl]propan-2-yl]phenol Chemical compound C=1C=C(OC(OC=2C=CC(=CC=2)C(C)(C)C=2C=CC(O)=CC=2)(OC=2C=CC(=CC=2)C(C)(C)C=2C=CC(O)=CC=2)OC=2C=CC(=CC=2)C(C)(C)C=2C=CC(O)=CC=2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 JHSDIILQGDBNPD-UHFFFAOYSA-N 0.000 description 1
- RQTDWDATSAVLOR-UHFFFAOYSA-N 4-[3,5-bis(4-hydroxyphenyl)phenyl]phenol Chemical compound C1=CC(O)=CC=C1C1=CC(C=2C=CC(O)=CC=2)=CC(C=2C=CC(O)=CC=2)=C1 RQTDWDATSAVLOR-UHFFFAOYSA-N 0.000 description 1
- CIEGINNQDIULCT-UHFFFAOYSA-N 4-[4,6-bis(4-hydroxyphenyl)-4,6-dimethylheptan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)CC(C)(C=1C=CC(O)=CC=1)CC(C)(C)C1=CC=C(O)C=C1 CIEGINNQDIULCT-UHFFFAOYSA-N 0.000 description 1
- RUCAFORHGFEQDF-UHFFFAOYSA-N 4-[[10-(4-hydroxyphenyl)anthracen-1-yl]methyl]phenol Chemical compound OC1=CC=C(CC2=CC=CC3=C(C4=CC=CC=C4C=C23)C2=CC=C(C=C2)O)C=C1 RUCAFORHGFEQDF-UHFFFAOYSA-N 0.000 description 1
- LIDWAYDGZUAJEG-UHFFFAOYSA-N 4-[bis(4-hydroxyphenyl)-phenylmethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)(C=1C=CC(O)=CC=1)C1=CC=CC=C1 LIDWAYDGZUAJEG-UHFFFAOYSA-N 0.000 description 1
- BOCLKUCIZOXUEY-UHFFFAOYSA-N 4-[tris(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 BOCLKUCIZOXUEY-UHFFFAOYSA-N 0.000 description 1
- QDQMEHXIUFCIGR-UHFFFAOYSA-N 4-ethyl-2-methylphenol Chemical compound CCC1=CC=C(O)C(C)=C1 QDQMEHXIUFCIGR-UHFFFAOYSA-N 0.000 description 1
- PBTXWTNXVCYRJA-UHFFFAOYSA-N 4-hept-2-enylphenol Chemical compound CCCCC=CCC1=CC=C(O)C=C1 PBTXWTNXVCYRJA-UHFFFAOYSA-N 0.000 description 1
- OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 1
- NKJIFDNZPGLLSH-UHFFFAOYSA-N 4-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=C(C#N)C=C1 NKJIFDNZPGLLSH-UHFFFAOYSA-N 0.000 description 1
- AYGGQJHJRFZDFH-UHFFFAOYSA-N 5,7-dichloro-1h-indole-2,3-dione Chemical compound ClC1=CC(Cl)=CC2=C1NC(=O)C2=O AYGGQJHJRFZDFH-UHFFFAOYSA-N 0.000 description 1
- MBVCESWADCIXJN-UHFFFAOYSA-N 5-Bromoisatin Chemical compound BrC1=CC=C2NC(=O)C(=O)C2=C1 MBVCESWADCIXJN-UHFFFAOYSA-N 0.000 description 1
- XHDJYQWGFIBCEP-UHFFFAOYSA-N 5-Chloro-1H-indole-2,3-dione Chemical compound ClC1=CC=C2NC(=O)C(=O)C2=C1 XHDJYQWGFIBCEP-UHFFFAOYSA-N 0.000 description 1
- MEXUTNIFSHFQRG-UHFFFAOYSA-N 6,7,12,13-tetrahydro-5h-indolo[2,3-a]pyrrolo[3,4-c]carbazol-5-one Chemical compound C12=C3C=CC=C[C]3NC2=C2NC3=CC=C[CH]C3=C2C2=C1C(=O)NC2 MEXUTNIFSHFQRG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229920005789 ACRONAL® acrylic binder Polymers 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- NDKYEUQMPZIGFN-UHFFFAOYSA-N Butyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCCC NDKYEUQMPZIGFN-UHFFFAOYSA-N 0.000 description 1
- PJNAUZOZOXDVBL-UHFFFAOYSA-N C=C.F.F.Cl.Cl Chemical compound C=C.F.F.Cl.Cl PJNAUZOZOXDVBL-UHFFFAOYSA-N 0.000 description 1
- GLEGDPIOGBBUMP-MWOVFPFUSA-N CC(C)(C)C(C(C(C(C)(C)C)=C1)=O)=CC1=C/N=N/c(cc1)ccc1Oc(cc1)ccc1/N=N/C=C(C=C1C(C)(C)C)C=C(C(C)(C)C)C1=O Chemical compound CC(C)(C)C(C(C(C(C)(C)C)=C1)=O)=CC1=C/N=N/c(cc1)ccc1Oc(cc1)ccc1/N=N/C=C(C=C1C(C)(C)C)C=C(C(C)(C)C)C1=O GLEGDPIOGBBUMP-MWOVFPFUSA-N 0.000 description 1
- YVSMVTXKIHCPEM-CYYJNZCTSA-N CC(C)(C)C(C(C(C(C)(C)C)=C1)=O)=CC1=C/N=N/c1ccc(C(F)(F)F)cc1 Chemical compound CC(C)(C)C(C(C(C(C)(C)C)=C1)=O)=CC1=C/N=N/c1ccc(C(F)(F)F)cc1 YVSMVTXKIHCPEM-CYYJNZCTSA-N 0.000 description 1
- ZNVMGZKCHWFGDC-VHXPQNKSSA-N CC(C)(C)C(C(C(C(C)(C)C)=C1)=O)=CC1=C/N=N\c(cc1)ccc1Cl Chemical compound CC(C)(C)C(C(C(C(C)(C)C)=C1)=O)=CC1=C/N=N\c(cc1)ccc1Cl ZNVMGZKCHWFGDC-VHXPQNKSSA-N 0.000 description 1
- ZMLIAWZVVPGHQO-UHFFFAOYSA-N CC(C=C(C=C1)C2=C(C=CC=C3)C3=CC3=CC=CC=C23)=C1O Chemical compound CC(C=C(C=C1)C2=C(C=CC=C3)C3=CC3=CC=CC=C23)=C1O ZMLIAWZVVPGHQO-UHFFFAOYSA-N 0.000 description 1
- XPEZVQDSLVQKOT-UHFFFAOYSA-N CC=C.C=C.F.F.F.F.F.F.F.F.F.F Chemical compound CC=C.C=C.F.F.F.F.F.F.F.F.F.F XPEZVQDSLVQKOT-UHFFFAOYSA-N 0.000 description 1
- QNJOXIYRXSHEOF-UHFFFAOYSA-N CCC(C(CC(N1)=O)C1=O)(C=C)I Chemical compound CCC(C(CC(N1)=O)C1=O)(C=C)I QNJOXIYRXSHEOF-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- RDOFJDLLWVCMRU-UHFFFAOYSA-N Diisobutyl adipate Chemical compound CC(C)COC(=O)CCCCC(=O)OCC(C)C RDOFJDLLWVCMRU-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PYVHTIWHNXTVPF-UHFFFAOYSA-N F.F.F.F.C=C Chemical compound F.F.F.F.C=C PYVHTIWHNXTVPF-UHFFFAOYSA-N 0.000 description 1
- WESZRJDUYAKEOH-UHFFFAOYSA-N FC=1C(=C(C(=C(C=1F)F)F)O)C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F Chemical compound FC=1C(=C(C(=C(C=1F)F)F)O)C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F WESZRJDUYAKEOH-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WZELXJBMMZFDDU-UHFFFAOYSA-N Imidazol-2-one Chemical class O=C1N=CC=N1 WZELXJBMMZFDDU-UHFFFAOYSA-N 0.000 description 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- BJIOGJUNALELMI-ONEGZZNKSA-N Isoeugenol Natural products COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- XVINFSJXLQUQNL-UHFFFAOYSA-N O=C(C(C(c1c2cccc1)=O)=C(c1ccccc1)C2=O)OCCCCCOC(C(C(c1ccccc11)=O)=C(c2ccccc2)C1=O)=O Chemical compound O=C(C(C(c1c2cccc1)=O)=C(c1ccccc1)C2=O)OCCCCCOC(C(C(c1ccccc11)=O)=C(c2ccccc2)C1=O)=O XVINFSJXLQUQNL-UHFFFAOYSA-N 0.000 description 1
- FJOQDVPYZSBBAX-UHFFFAOYSA-N O=C(C(C(c1c2cccc1)=O)=C(c1ccccc1)C2=O)OCc1ccccc1 Chemical compound O=C(C(C(c1c2cccc1)=O)=C(c1ccccc1)C2=O)OCc1ccccc1 FJOQDVPYZSBBAX-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229910001370 Se alloy Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- QHWKHLYUUZGSCW-UHFFFAOYSA-N Tetrabromophthalic anhydride Chemical compound BrC1=C(Br)C(Br)=C2C(=O)OC(=O)C2=C1Br QHWKHLYUUZGSCW-UHFFFAOYSA-N 0.000 description 1
- UATJOMSPNYCXIX-UHFFFAOYSA-N Trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 UATJOMSPNYCXIX-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 229920002433 Vinyl chloride-vinyl acetate copolymer Polymers 0.000 description 1
- 229920001986 Vinylidene chloride-vinyl chloride copolymer Polymers 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- PQCCZSBUXOQGIU-UHFFFAOYSA-N [La].[Pb] Chemical compound [La].[Pb] PQCCZSBUXOQGIU-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- DCBMHXCACVDWJZ-UHFFFAOYSA-N adamantylidene Chemical group C1C(C2)CC3[C]C1CC2C3 DCBMHXCACVDWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000006193 alkinyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 description 1
- 229910002113 barium titanate Inorganic materials 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 description 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 229940114055 beta-resorcylic acid Drugs 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
- NWRJMFCZZOMPSU-UHFFFAOYSA-N bis(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl) 5-hydroxybenzene-1,3-dicarboxylate Chemical compound OC1=CC(C(=O)OC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)=CC(C(=O)OC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)=C1 NWRJMFCZZOMPSU-UHFFFAOYSA-N 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- HSUIVCLOAAJSRE-UHFFFAOYSA-N bis(2-methoxyethyl) benzene-1,2-dicarboxylate Chemical compound COCCOC(=O)C1=CC=CC=C1C(=O)OCCOC HSUIVCLOAAJSRE-UHFFFAOYSA-N 0.000 description 1
- IRFCWUHTGYXRNR-UHFFFAOYSA-N bis(4-nitrophenyl)methanone Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)C1=CC=C([N+]([O-])=O)C=C1 IRFCWUHTGYXRNR-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229910052798 chalcogen Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- BJIOGJUNALELMI-ARJAWSKDSA-N cis-isoeugenol Chemical compound COC1=CC(\C=C/C)=CC=C1O BJIOGJUNALELMI-ARJAWSKDSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229920006026 co-polymeric resin Polymers 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001907 coumarones Chemical class 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- ZXJXZNDDNMQXFV-UHFFFAOYSA-M crystal violet Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1[C+](C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 ZXJXZNDDNMQXFV-UHFFFAOYSA-M 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- 125000004976 cyclobutylene group Chemical group 0.000 description 1
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005070 decynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 229960002380 dibutyl phthalate Drugs 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229940031769 diisobutyl adipate Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 1
- NKZSPGSOXYXWQA-UHFFFAOYSA-N dioxido(oxo)titanium;lead(2+) Chemical compound [Pb+2].[O-][Ti]([O-])=O NKZSPGSOXYXWQA-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- WTOSNONTQZJEBC-UHFFFAOYSA-N erythrosin Chemical compound OC(=O)C1=CC=CC=C1C(C1C(C(=C(O)C(I)=C1)I)O1)=C2C1=C(I)C(=O)C(I)=C2 WTOSNONTQZJEBC-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910001849 group 12 element Inorganic materials 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 231100000206 health hazard Toxicity 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000002461 imidazolidines Chemical class 0.000 description 1
- 229940097275 indigo Drugs 0.000 description 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000000752 ionisation method Methods 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- 125000005921 isopentoxy group Chemical group 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
- YYGBVRCTHASBKD-UHFFFAOYSA-M methylene green Chemical compound [Cl-].C1=CC(N(C)C)=C([N+]([O-])=O)C2=[S+]C3=CC(N(C)C)=CC=C3N=C21 YYGBVRCTHASBKD-UHFFFAOYSA-M 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- JULPEDSLKXGZKK-UHFFFAOYSA-N n,n-dimethyl-1h-imidazole-5-carboxamide Chemical compound CN(C)C(=O)C1=CN=CN1 JULPEDSLKXGZKK-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000006610 n-decyloxy group Chemical group 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000006609 n-nonyloxy group Chemical group 0.000 description 1
- 125000006608 n-octyloxy group Chemical group 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 125000005484 neopentoxy group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- NTPMRTUYLKDNSS-UHFFFAOYSA-N night blue Chemical compound [Cl-].C1=CC(N(CC)CC)=CC=C1C(C=1C2=CC=CC=C2C(NC=2C=CC=CC=2)=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 NTPMRTUYLKDNSS-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- QBDSZLJBMIMQRS-UHFFFAOYSA-N p-Cumylphenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=CC=C1 QBDSZLJBMIMQRS-UHFFFAOYSA-N 0.000 description 1
- NKTOLZVEWDHZMU-UHFFFAOYSA-N p-cumyl phenol Natural products CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 1
- NRNFFDZCBYOZJY-UHFFFAOYSA-N p-quinodimethane Chemical class C=C1C=CC(=C)C=C1 NRNFFDZCBYOZJY-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 description 1
- BPHQIXJDBIHMLT-UHFFFAOYSA-N perfluorodecane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F BPHQIXJDBIHMLT-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- NAKOELLGRBLZOF-UHFFFAOYSA-N phenoxybenzene;pyrrole-2,5-dione Chemical compound O=C1NC(=O)C=C1.O=C1NC(=O)C=C1.C=1C=CC=CC=1OC1=CC=CC=C1 NAKOELLGRBLZOF-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920006350 polyacrylonitrile resin Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- RCYFOPUXRMOLQM-UHFFFAOYSA-N pyrene-1-carbaldehyde Chemical compound C1=C2C(C=O)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 RCYFOPUXRMOLQM-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 229940065287 selenium compound Drugs 0.000 description 1
- 150000003343 selenium compounds Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005922 tert-pentoxy group Chemical group 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000001016 thiazine dye Substances 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 1
- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical class C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- JEVGKYBUANQAKG-UHFFFAOYSA-N victoria blue R Chemical compound [Cl-].C12=CC=CC=C2C(=[NH+]CC)C=CC1=C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 JEVGKYBUANQAKG-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Images
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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/20—General preparatory processes
- C08G64/22—General preparatory processes using carbonyl halides
- C08G64/24—General preparatory processes using carbonyl halides and phenols
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/18—Block or graft polymers
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
- C08G63/185—Acids containing aromatic rings containing two or more aromatic rings
- C08G63/187—Acids containing aromatic rings containing two or more aromatic rings containing condensed aromatic rings
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/91—Polymers modified by chemical after-treatment
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
- C08G64/14—Aromatic polycarbonates not containing aliphatic unsaturation containing a chain-terminating or -crosslinking agent
-
- 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
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
-
- 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
- C08G85/00—General processes for preparing compounds provided for in this subclass
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
- C08L67/03—Polyesters derived from dicarboxylic acids and dihydroxy compounds the dicarboxylic acids and dihydroxy compounds having the carboxyl- and the hydroxy groups directly linked to aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D169/00—Coating compositions based on polycarbonates; Coating compositions based on derivatives of polycarbonates
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
- G03G5/0525—Coating methods
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
- G03G5/0528—Macromolecular bonding materials
- G03G5/0557—Macromolecular bonding materials obtained otherwise than by reactions only involving carbon-to-carbon unsatured bonds
- G03G5/0564—Polycarbonates
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
- G03G5/0528—Macromolecular bonding materials
- G03G5/0592—Macromolecular compounds characterised by their structure or by their chemical properties, e.g. block polymers, reticulated polymers, molecular weight, acidity
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/02—Charge-receiving layers
- G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
- G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
- G03G5/07—Polymeric photoconductive materials
- G03G5/075—Polymeric photoconductive materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/14—Inert intermediate or cover layers for charge-receiving layers
- G03G5/147—Cover layers
Definitions
- the present invention relates to a resin, a resin precursor composition, a coating liquid composition, an electrophotographic photosensitive member, a molded product, an electronic device, and a method for producing an electrophotographic photosensitive member.
- Polycarbonate resin has been used as a material for molded products in various industrial fields because it has excellent mechanical, thermal, and electrical properties.
- polycarbonate resins have been widely used in the field of functional products that also utilize their optical properties. With the expansion of such fields of application, the required performance for polycarbonate resins has diversified, and not only polycarbonate resins that have been conventionally used but also polycarbonate resins having various chemical structures have been proposed.
- An example of a functional product is an organic electrophotographic photosensitive member in which a polycarbonate resin is used as a binder resin for a functional material such as a charge generating material or a charge transporting material.
- the organic electrophotographic photosensitive member is required to have predetermined sensitivity, electrical characteristics, and optical characteristics according to the electrophotographic process to be applied.
- operations such as corona charging, toner development, transfer to paper, and cleaning processing are repeatedly performed on the surface of the photosensitive layer, and therefore, an electrical or mechanical external force is applied each time these operations are performed. Is added.
- the photosensitive layer provided on the surface of the electrophotographic photosensitive member is required to have durability against these external forces.
- the organic electrophotographic photosensitive member is usually manufactured by a method in which a binder resin is dissolved in an organic solvent together with a functional material and cast film is formed on a conductive substrate or the like, the solubility and stability in the organic solvent are high. Desired.
- a binder resin for a photoconductor a polycarbonate resin made from 2,2-bis (4-hydroxyphenyl) propane, 1,1-bis (4-hydroxyphenyl) cyclohexane, or the like has been used, but it is durable. I was not fully satisfied with the sex. As one of the measures for improving the durability, it is conceivable to improve the wear resistance of the photosensitive layer. As an effective technique for improving the wear resistance of the photosensitive layer, a technique for cross-linking polycarbonate is known.
- Patent Document 2 describes a resin crosslinked by an ionic mechanism such as an epoxy group in a polycarbonate copolymer.
- Patent Document 3 describes cross-linking by reacting a polycarbonate having a double bond with a compound having a plurality of silicon-hydrogen bonds in the presence of a platinum catalyst, and an alkoxy group on the polycarbonate having a double bond and a silicon atom.
- a cross-linking technique is described in which a compound having hydrogen is reacted in the presence of a platinum catalyst, and then a hydrolysis and a condensation reaction are carried out.
- Patent Document 4 discloses a cross-linking technique in which a polycarbonate having an allyl group is irradiated with an electron beam in a state of being heated from 120 ° C. to 260 ° C.
- Patent Document 5 discloses a method of cross-linking a polycarbonate having an allyl group by heating without a catalyst using a triarylamine having a specific structure and a radically polymerizable compound having no triarylamine structure.
- Patent Document 6 reports a resin obtained by extending the chain length of a resin having an anthracene skeleton at the end of an aliphatic-aromatic polyester with bismaleimide. Further, Patent Document 7 discloses a crosslinked resin obtained by reacting an aliphatic polyester having a furan structure, a polyamide, or a polyurea with a polyfunctional maleimide. Patent Document 8 discloses a curable composition in which a polymerizable functional group such as an acrylic group is introduced into the anthracene skeleton and a cross-linking reaction is carried out at the portion of the functional group.
- a polymerizable functional group such as an acrylic group
- Non-Patent Document 1 discloses a resin obtained by cross-linking a resin in which an anthracene dicarboxylic acid skeleton is introduced into a part of an aliphatic-aromatic polyester with a bifunctional maleimide compound.
- cross-linked polycarbonate and polyarylates can be obtained without radical initiators or reaction catalysts that cause deterioration of electrical properties, and without the use of UVs and electron beams that alter CTM.
- Patent Document 5 uses a monomer having high radical polymerization activity and radically polymerizing only by heating without using an initiator or UV irradiation, and a technique for coexisting polycarbonate having an allyl group therein. Has been reported.
- the obtained composition does not have a dense three-dimensional network structure of the polymer, but a crosslinked polymer of the polycarbonate resin and the radical polymerization monomer exists separately, and only a part thereof is bonded to the composition. It is thought that there is.
- Patent Document 6 discloses a linear polymer obtained by a molecular weight extension reaction of an aliphatic-aromatic polyester by a Diels-Alder reaction as an example using a resin other than polycarbonate. ing.
- an object of the invention described in Patent Document 6 is to utilize the fact that the bonds formed by the Diels-Alder reaction cause a retro-Diels-Alder reaction that dissociates at a high temperature, and the melt viscosity is lowered by lowering the viscosity at a high temperature.
- Patent Document 6 does not describe or suggest that the technique described in Patent Document 6 is applied to aromatic polycarbonate or all aromatic polyester.
- Patent Document 7 describes an example in which an aliphatic polyester, a polyamide, or a polyurea is crosslinked by a Diels-Alder reaction.
- these examples are aimed at imparting solvent resistance by cross-linking a soft aliphatic resin and obtaining an elastomer applicable to a diaphragm seal or an adhesive intended for use.
- the technical idea of these examples is different from the idea of the present invention in which aromatic polycarbonate having high mechanical strength and all aromatic polyester are further increased in strength by cross-linking.
- Patent Document 7 does not describe or suggest that the technique described in Patent Document 7 is applied to aromatic polycarbonate or all aromatic polyester.
- Non-Patent Document 1 describes an example in which an anthracene dicarboxylic acid skeleton is introduced into polyethylene terephthalate (PET) and crosslinked with a bifunctional maleimide compound.
- PET polyethylene terephthalate
- the object of this example is similar to the object of the present invention in that the mechanical properties are improved by heat crosslinking, but Non-Patent Document 1 does not describe or suggest an example of application to polycarbonate or polyarylate.
- PET has low solubility in an organic solvent such as THF, which is usually used as a coating solvent, and is compatible with a charge transporting substance such as triarylamine, considering that it is used for an electrophotographic photosensitive member. It is bad and cannot be used for this purpose.
- Patent Document 8 discloses an example in which a polymerizable functional group such as an acrylic group is introduced into the anthracene skeleton and a cross-linking reaction is carried out at the portion of the functional group.
- Patent Document 8 does not describe or suggest the use of the anthracene moiety for the cross-linking reaction.
- the invention described in Patent Document 8 aims to retain the function of the anthracene skeleton, and the technique of the present invention applying the Diels-Alder reaction that eliminates the anthracene skeleton by the reaction is contrary to the object. There is.
- the first object of the present invention is that it does not contain a radical initiator or a reaction catalyst that causes deterioration of electrical properties, and can be produced without using UV or an electron beam that alters a charge transporter (CTM). It is an object of the present invention to provide at least one resin of aromatic polycarbonate and polyarylate having a novel structure, which is substantially free of a polymer containing only a single component when there are a plurality of polymerizable components.
- a second object of the present invention is to provide a resin precursor composition and a coating liquid composition, which have a characteristic that the reaction at the stage of the coating liquid composition is unlikely to occur and the characteristic change is small.
- a third object of the present invention is to provide an electrophotographic photosensitive member which is excellent in solvent resistance and abrasion resistance, is less likely to cause mechanical deterioration, and does not deteriorate the residual potential by containing the resin. Is.
- a characteristic resin is provided.
- a resin precursor composition characterized in that the resin according to the above-mentioned one aspect of the present invention can be produced by a cross-linking reaction.
- a coating composition comprising the resin precursor composition according to the above-mentioned aspect of the present invention and an organic solvent.
- an electrophotographic photosensitive member characterized in that the outermost layer contains the resin according to the above-mentioned aspect of the present invention.
- the organic composition in the coating composition is formed by applying the coating composition according to the above aspect of the present invention to a conductive substrate by a wet molding method and heating. It comprises a step of removing the solvent and a step of performing a cross-linking reaction of the resin precursor composition in the coating liquid composition by simultaneously or continuously heating the heating in the step of removing the organic solvent.
- a method for producing an electrophotographic photosensitive member is provided.
- a molded product comprising the resin according to the above-mentioned one aspect of the present invention.
- an electronic device comprising the resin according to the above-mentioned aspect of the present invention.
- At least one of the aromatic polycarbonate and polyarylate resins does not contain a radical initiator or reaction catalyst that causes deterioration of electrical properties, and a charge transport material (CTM) is used.
- CTM charge transport material
- an electrophotographic photosensitive member having excellent solvent resistance, excellent wear resistance, less mechanical deterioration, and no deterioration of residual potential is provided. be able to.
- the resin according to this embodiment is at least one resin selected from the group consisting of aromatic polycarbonate and polyarylate.
- Specific examples of the resin include aromatic polycarbonate, polyarylate, and aromatic polycarbonate-polyarylate copolymer (hereinafter, these are also simply referred to as “PCs”).
- the resin according to this embodiment has a bond between polymer chains by the Diels-Alder reaction. Further, the resin having a bond between polymer chains has a structure represented by the following general formula (S1). In the following general formula (S1), * represents a coupling position.
- the structure of the portion ahead of the wavy line is not particularly limited, but any of the portions ahead of the wavy line has at least one coupling position.
- the portion beyond the wavy line may form a connected cyclic structure (including an aromatic ring and a heterocycle).
- the aromatic ring and the heterocycle may be any of a 3-membered ring, a 4-membered ring, a 5-membered ring, a 6-membered ring, a 7-membered ring and the like.
- the structure of the cross-linking site that bonds the polymer chains is, for example, a bonding mode as shown by the following general formula.
- the cross-linking mode according to the present embodiment is different from the cross-linking by a general radical reaction which has a linear structure in that it has a rigid cyclic structure. It is considered that having a cyclic structure makes the structure stronger than the linear cross-linking, which contributes to the improvement of the mechanical strength compared to the linear cross-linking type resin having the same cross-linking density. Be done.
- the present inventors have excellent solution stability of PCs crosslinked by the Diels-Alder reaction at the current temperature of the photoconductor manufacturing process. It was found that the crosslinked resin obtained after cross-linking had excellent wear resistance and no deterioration in electrical characteristics was observed. The present invention has been completed based on such findings.
- the resin according to the present embodiment has a cross-linking reaction with a combination of a polymer having at least one of Diels-Alder-reactive conjugated diene and dienophile in its structure and a cross-linking agent or polymer having each partner's group. Can be obtained.
- the bond between the polymer chains according to the present embodiment can be formed by, for example, the following combination of reactions.
- the bond between the polymer chains in the resin according to the present embodiment may be, for example, the reaction of (i-1) below.
- (I-1) Reaction of a polymer having two or more conjugated diene structures in the main chain of a polymer chain with a compound having a bifunctional or higher functional dienefil group
- the bond between the polymer chains in the resin according to the present embodiment may be, for example, at least one of the following reactions (iii-1) to (iii-8).
- (Iii-2) A polymer having two Dielsophil structures and having one Dielsophil structure at each end of the polymer chain, A polymer having more than two conjugated diene structures in a polymer chain, having one conjugated diene structure at both ends of the polymer chain, and one conjugated diene structure in the main chain. Reaction with the polymer having the above
- (Iii-3) A polymer having two Dielsophil structures and having one Dielsophil structure at each end of the polymer chain, A polymer having more than two conjugated diene structures in a polymer chain, having one conjugated diene structure at one end of the polymer chain and having the conjugated diene structure at the other end. Reaction with a polymer having two or more of the conjugated diene structures in the main chain
- (Iii-4) A polymer having two Dielsophil structures and having one Dielsophil structure at each end of the polymer chain, Reaction with a polymer that does not have a conjugated diene structure at both ends of the polymer chain and has more than two conjugated diene structures in the main chain.
- (Iii-7) A polymer having two conjugated diene structures and having one conjugated diene structure at both ends of the polymer chain, A polymer having more than two dienophile structures in a polymer chain, having one dienophile structure at one end of the polymer chain, having no dienophile structure at the other end, and a main chain. Reaction with a polymer having two or more dienophile structures inside
- (Iii-8) A polymer having two conjugated diene structures and having one conjugated diene structure at both ends of the polymer chain, Reaction with a polymer that does not have a Dielsophil structure at both ends of the polymer chain and has more than two Dielsophil structures in the main chain.
- the polymer used for bonding between polymer chains in the resin according to the present embodiment does not have at least two or more conjugated diene structures and dienophile structures at the ends of the polymer chains.
- the conjugated diene structure in a polymer having two or more conjugated diene structures, is bound to at least one end of one end and the other end of the polymer chain. It does not have to be, and the conjugated diene structure may not be bound to the end of the polymer chain.
- the Diels-Alder structure in a polymer having two or more Diels-Alder structures, is not bound to at least one end of one end and the other end of the polymer chain.
- the Dielsophil structure may not be bound to the end of the polymer chain.
- the conjugated diene structure in a polymer having two or more conjugated diene structures, is bound to at least one end of one end and the other end of the polymer chain.
- the dienophile structure may not be bound to at least one end of one end and the other end of the polymer chain, and , The conjugated diene structure and the dienophile structure may not be bonded to the end of the polymer chain.
- the polymer used for bonding between polymer chains in the resin according to the present embodiment preferably has at least one of a conjugated diene structure and a dienophile structure in the main chain of the polymer chains.
- one or more conjugated diene structures may be bonded to the main chain of the polymer chain, or the polymer chain. All conjugated diene structures may be attached to the main chain of.
- one or more dielsophile structures may be bonded to the main chain of the polymer chain, or the main chain of the polymer chain. All dienophile structures may be attached to the chain.
- one or more conjugated diene structures are bonded to the main chain of the polymer chain, and two or more dienophile structures are formed.
- one or more dienophile structures may be bonded to the main chain of the polymer chain.
- all the conjugated diene structures are bonded to the main chain of the polymer chain, and two or more dienophile structures are formed.
- all the dienophile structures may be bonded to the main chain of the polymer chain.
- the conjugated diene structure or the dienophile structure may be directly bonded to the main chain of the polymer chain, or the polymer may be directly bonded to the main chain of the polymer chain. It may be attached to the main chain of the chain.
- the polymer used for bonding between polymer chains in the resin according to the present embodiment does not have at least two or more conjugated diene structures and dienophile structures at the ends of the polymer chains.
- examples of the polymer having both a conjugated diene structure and a Dielsophil structure in one polymer chain include polymers having the following aspects.
- (Iv-1) A polymer in which a conjugated diene structure and a dienophile structure are not bound to at least one end of one end and the other end of the polymer chain
- (iv-2) One end of the polymer chain One of the conjugated diene structure and the dienophile structure is bound to the molecule, and neither the conjugated diene structure nor the dienophile structure is bound to the other end of the polymer chain.
- Molecules to which at least one of the other structures is bonded iv-3 A molecule to which a conjugated diene structure and a dienophile structure are not bonded to the end of a polymer chain.
- the polymer used for bonding between polymer chains in the resin according to the present embodiment preferably has at least one of a conjugated diene structure and a dienophile structure in the main chain of the polymer chains.
- either a conjugated diene structure or a dienophile structure is attached to the main chain of the polymer chain.
- One or more may be bonded, or all conjugated diene structures and dienophile structures may be bonded to the main chain of the polymer chain.
- examples of the polymer having both a conjugated diene structure and a Dielsophil structure in one polymer chain include polymers having the following aspects.
- (Iv-4) A polymer in which one dienophile structure is bonded to both ends of the polymer chain and at least one conjugated diene structure is bonded to the main chain of the polymer chain.
- the conjugated diene structure or the dienophile structure may be directly bonded to the main chain of the polymer chain, or the polymer may be directly bonded to the main chain of the polymer chain. It may be attached to the main chain of the chain.
- the bonds between the polymer chains in the resin according to the present embodiment are not only the bonds between the ends of the polymer chains. That is, the bonds between the polymer chains in the resin according to the present embodiment are bonded to one of the conjugated diene structure and the dienophile structure bonded to the end of one polymer and the main chain of the other polymer. Bonded to the other of the conjugated diene and dienophile structures, or to the main chain of one of the conjugated diene and dienophile structures and to the main chain of the other polymer. It is also preferable to have at least one of a conjugated diene structure and a bond with the other of the dienophile structure.
- the bonds are not made only between the ends of the polymer chains, three-dimensional cross-linking between the polymer chains occurs, and the solvent resistance of the resin can be easily improved. Further, even if the ends of the polymer chains are not bonded to each other, the three-dimensional cross-linking does not occur in the case of the bonds between the polymer chains having two reactive groups, and the polymer becomes a linear polymer. Therefore, the bond between the polymer chains in the resin according to the present embodiment is limited to the polymers having two reaction points (reactive groups) in the polymer chains (for example, the polymers having a reactive group at the end). It is also preferable that the binding is not due to the reaction of.
- the bond between the polymer chains in the resin according to the present embodiment may include a bond between the ends of the polymer chains.
- any structure that causes a Diels-Alder reaction can be applied, but a structure having an anthracene skeleton, a furan skeleton, and a styryl skeleton is preferably used because of its high reactivity.
- the conjugated diene structure includes dihydroxyanthracene, anthracene dicarboxylic acid, 9- (4-hydroxybenzyl) -10- (4-hydroxyphenyl) anthracene, and 9- (3-methyl-4-hydroxybenzyl) -10- (3-).
- Methyl-4-hydroxyphenyl) anthracene 9- (4-hydroxyphenyl) anthracene, 9- (3-methyl-4-hydroxyphenyl) anthracene, 9,10-bis (4-hydroxyphenyl) anthracene, 9,10- Groups derived from bis (3-methyl-4-hydroxyphenyl) anthracene, hydroxyanthracene, 1,4-dihydroxyanthracene, anthracene carboxylic acid, 2- (2-furanylmethyl) hydroquinone, flange carboxylic acid, isoeugenol, etc. Can be mentioned.
- conjugated diene structure or the conjugated diene group is at least one structure represented by the following general formula (DE1) and general formula (DE2). Is preferably included.
- R 1 is independent of each other Single bond, Bonding groups with other skeletons, Hydrogen atom, Aliphatic hydrocarbon groups with 1 or more carbon atoms and 12 or less carbon atoms, Ring-forming An aromatic hydrocarbon group having 6 or more carbon atoms and 12 or less carbon atoms, or an alkoxy group having 1 or more carbon atoms and 10 or less carbon atoms.
- R 1 is a linking group with a single bond or other skeleton
- R 1 as the linking group contains at least one atom selected from the group consisting of a carbon atom, an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom and a boron atom, and is an atom constituting the linking group. It is a group in which all the bonding modes of each other are covalent bonds. Further, a cyclic structure (including an aromatic ring and a heterocycle) in which a plurality of R 1s are connected may be formed.
- the alkyl group as an aliphatic hydrocarbon group having 1 or more carbon atoms and 12 or less carbon atoms includes, for example, a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group and an isopropyl group.
- Isobutyl group, sec-butyl group, tert-butyl group, isopentyl group, neopentyl group, tert-pentyl group, isohexyl group, sec-hexyl group, tert-hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl Groups, dodecyl groups and the like can be mentioned.
- the alkenyl group as an aliphatic hydrocarbon group having 1 or more carbon atoms and 12 or less carbon atoms is, for example, a vinyl group (ethenyl group, 1-propenyl group, 2-propenyl group, 2-butenyl group, 1-butenyl group, 1-hexenyl group.
- Examples include groups, octenyl groups, decenyl groups, dodecenyl groups and the like.
- the alkynyl group as an aliphatic hydrocarbon group having 1 or more carbon atoms and 12 or less carbon atoms includes, for example, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 3-hexynyl group, an octynyl group and a decynyl group. And dodecynyl groups and the like.
- R 1 represents ring carbon atoms of 6 or more, 12 or less of the aromatic hydrocarbon group is, for example, be mentioned a phenyl group, a naphthyl group and biphenyl group, ..
- the alkoxy groups having 1 or more and 10 or less carbon atoms represented by R 1 are methoxy group, ethoxy group, n-propoxy group, n-butoxy group and n-pentyloxy.
- R 1 as the linking group is a carbon atom, an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, at least is selected from the group consisting of phosphorus and boron atoms
- a divalent group containing any of the atoms can be mentioned.
- a divalent aromatic hydrocarbon group may be contained in the structure of this divalent group. Examples of the divalent aromatic hydrocarbon group include a phenylene group (-Ph-), a naphthylene group, and biphenylene.
- the conjugated diene contains at least one of the structures represented by the following general formulas (DE3) to (DE8).
- R 12 are each independently Hydrogen atom, An aliphatic hydrocarbon group having 1 or more carbon atoms and 12 or less carbon atoms, or an aromatic hydrocarbon group having 6 or more carbon atoms and 12 or less carbon atoms.
- n represents 0 or a natural number up to a replaceable number. * Indicates the bonding position.
- the conjugated diene contains at least one of the structures represented by the following general formulas (DE9) to (DE16).
- R 13 are independent of each other Hydrogen atom, It is an aliphatic hydrocarbon group having 1 or more carbon atoms and 12 or less carbon atoms, or an aromatic hydrocarbon group having 6 or more carbon atoms and 12 or less carbon atoms.
- R 13 are independent of each other It is preferably an aliphatic hydrocarbon group having 1 or more carbon atoms and 12 or less carbon atoms, or an aromatic hydrocarbon group having 6 or more carbon atoms and 12 or less carbon atoms. * Indicates the bonding position.
- the conjugated diene preferably contains at least one of the structures represented by the following general formula (DE17) and general formula (DE18).
- R 11 are independent of each other Hydrogen atom, Halogen atom, Aliphatic hydrocarbon groups with 1 or more carbon atoms and 12 or less carbon atoms, Ring-forming An aromatic hydrocarbon group having 6 or more carbon atoms and 12 or less carbon atoms, or an alkoxy group having 1 or more carbon atoms and 10 or less carbon atoms. Further, a cyclic structure (including an aromatic ring and a heterocycle) in which a plurality of R 11s are connected may be formed.
- m represents an integer of 0 or more and 8 or less.
- n represents an integer of 0 or more and 4 or less.
- m represents an integer of 0 or more and 9 or less. * Indicates the bonding position.
- the conjugated diene preferably contains at least one of the structures represented by the following general formula (DE19).
- R 11 are independent of each other Hydrogen atom, Halogen atom, Aliphatic hydrocarbon groups with 1 or more carbon atoms and 12 or less carbon atoms, Ring-forming An aromatic hydrocarbon group having 6 or more carbon atoms and 12 or less carbon atoms, or an alkoxy group having 1 or more carbon atoms and 10 or less carbon atoms. Further, a cyclic structure (including an aromatic ring and a heterocycle) in which a plurality of R 11s are connected may be formed. n represents an integer of 0 or more and 3 or less. * Indicates the bonding position.
- the dienophile structure any structure that causes a Diels-Alder reaction can be applied, but a structure having a maleimide skeleton is preferably used because of its high reactivity.
- the dienophile structure includes 4,4'-diphenylmethanebismaleimide, m-phenylene bismaleimide, 2,2-bis [4- (4-maleimidephenoxy) phenyl] propane, bisphenol A diphenyl ether bismaleimide, 3,3'-dimethyl.
- the Diels-Alder structure or Diels-Alder group (hereinafter, these are also simply referred to as "Diels-Alder”) preferably contains a structure represented by the following general formula (DP1).
- X 2 is a single bond or a linking group with another skeleton
- X 2 as the linking group contains at least one atom selected from the group consisting of a carbon atom, an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, a phosphorus atom and a boron atom, and is an atom constituting the linking group. It is a group in which all the bonding modes of each other are covalent bonds. * Indicates the bonding position.
- Diels-Alder is contained in at least one of the structures represented by the following general formula (DP2) and general formula (DP3).
- X 2 in the general formula (DP2) and X 21 and X 22 in the general formula (DP3) are independently synonymous with X 2 in the general formula (DP1).
- Y 2 in the general formula (DP3) is a group containing an aromatic polycarbonate skeleton or a polyarylate skeleton.
- the Diels-Alder structure or Diels-Alder group contains a structure represented by the following general formula (DP4).
- DP4 general formula (DP4)
- * indicates a binding position.
- the ratio of the conjugated diene to the dienophile can be appropriately set according to the target physical properties and the target application.
- the molar ratio of conjugated diene to dienophile is preferably 0.01 or more and 100 or less, more preferably 0.1 or more and 10 or less, and 0.2 or more and 5 or less. It is more preferable to have. If the molar ratio of conjugated diene to dienophile is less than 0.01 or more than 100, cross-linking may not proceed sufficiently and the improvement of solvent resistance and mechanical properties may be insufficient.
- the resin according to this embodiment preferably contains at least one of the structures represented by the following general formulas (UN1) and general formula (UN2).
- R 3 are each independently a hydrogen atom, Halogen atom, Alkyl with 1 or more and 10 or less carbon atoms, Ring-forming Aryl having 6 or more carbon atoms and 12 or less carbon atoms, or alkyl fluoride having 1 or more carbon atoms and 10 or less carbon atoms.
- R 31 to R 34 are independent of each other. Hydrogen atom, Halogen atom, Alkyl with 1 or more and 10 or less carbon atoms, Ring-forming Aryl having 6 or more carbon atoms and 12 or less carbon atoms, or alkyl fluoride having 1 or more carbon atoms and 10 or less carbon atoms. * Indicates the bonding position.
- examples of the halogen atom represented by R 3 include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- alkyl having 1 or more and 10 or less carbon atoms represented by R 3 is, for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-.
- examples of the aryl having 6 or more and 12 or less ring-forming carbon atoms represented by R 3 include groups such as phenyl, naphthyl, and biphenyl.
- R 3 has 1 or more carbon atoms shown, 10 following fluorinated alkyl is, for example, R 3 has 1 or more carbon atoms shown in the above general formula (UN11), exemplified by 10 an alkyl
- an alkyl group in which at least one hydrogen atom of a carbon atom is replaced with a fluorine atom can be mentioned.
- X 3 is carbon number 2 or more which indicates, 20 following alkylene include straight-chain or branched alkylene group such as ethylene, propylene, isopropylene, xylene butylene, to, Groups such as octylene and decylene can be mentioned.
- X 3 is carbon showing 2 or more, 20 or less alkylidene, ethylidene, propylidene, butylidene, hexylidene, octylidene, decylidene, Pentadeshiriden include groups such as Ikoshiriden.
- X 3 is carbon indicates 3 or more, 20 or less cycloalkylene, for example, linear or branched alkylene group, for example, xylene cyclopropylene, cyclobutylene, cyclohexylene, cycloheteroalkyl Groups such as octylene, cyclodecylene, cyclopentadecylene, and cycloicosilene can be mentioned.
- cycloalkylidene having 3 or more carbon atoms and 20 or less carbon atoms represented by X 3 is cyclopropylidene, cyclobutylidene, cyclohexylidene, cyclooctylidene, cyclodecylidene, cyclododecylidene, cyclopentadesi. Examples include groups such as lidene, and cycloicosilidene.
- X 3 represents ring carbon atoms of 6 or more, 20 or less arylene such as phenylene, naphthylene, and groups such as biphenylene like.
- the bicycloalkanediyl having 4 or more and 20 or less ring-forming carbon atoms represented by X 3 is, for example, the above-mentioned cycloalkylene dicyclic body, and has 5 or more and 20 or less ring-forming carbon atoms.
- the tricycloalkanediyl of the above include the above-mentioned cycloalkylene tricycles, for example, tricyclodecanediyl and adamantandiyl.
- X 3 represents ring carbon atoms of 4 or more, 20 or less bicycloalkyl alkylidene is bicyclic body above cycloalkylidene is illustrated, ring carbon atoms of 5 or more, 20 or less tricyclo
- alkylidene include the above-mentioned tricyclics of cycloalkylidene, such as adamantylidene and tricyclodecylidene.
- halogen atoms represented by R 31 to R 34 of X 3 alkyl having 1 or more and 10 or less carbon atoms, aryl having 6 or more and 12 or less ring-forming carbon atoms, and 1 or more and 10 carbon atoms.
- alkyl fluorides include groups similar to the group represented by R 3 in the above general formula (UN11).
- the resin precursor composition according to the present embodiment can produce the above-mentioned resin according to the present embodiment by a cross-linking reaction. That is, the resin precursor composition according to the present embodiment includes a polymer having at least one of Diels-Alder-reactive conjugated diene and dienophile in its structure, and a cross-linking agent or polymer having a group of each partner. And are included in combination.
- the conjugated diene, dienefil, and the ratio of the conjugated diene to the dienophile are the same as those of the resin according to the present embodiment.
- the concentrations of conjugated diene and dienophile in the resin precursor composition according to the present embodiment can be appropriately set according to the target physical properties and the target application. Calculated based on the total number of moles of conjugated diene and the total number of moles of dienophile, whichever is smaller, with respect to the total amount of composition having Diels-Alder reactive groups (at least one of conjugated diene and dienophile).
- the functional group concentration is preferably 0.01 mmol / g or more and 10 mmol / g or less, and more preferably 0.03 mmol / g or more and 7 mmol / g or less.
- the functional group concentration is less than 0.01 mmol / g, the crosslink density is small and the improvement of solvent resistance and mechanical properties may be insufficient.
- the functional group concentration exceeds 10 mmol / g, the cross-linking density is too high and the toughness of the cross-linked product is insufficient, or unreacted functional groups are likely to remain, and the cross-linking reaction and other side reactions proceed over time. This is not preferable because the physical properties of the material are likely to change or deteriorate.
- the resin precursor composition according to the present embodiment preferably contains, for example, at least one of the following components (b1) to (b4).
- B1 A polymer having two or more conjugated diene structures in a polymer chain and a compound having a bifunctional or higher dienofil group
- b2 A polymer having two or more dienofil structures in a polymer chain and a bifunctional Compound having the above conjugated diene group
- b3 Polymer having two or more conjugated diene structures in the polymer chain and polymer having two or more dienophile structures in the polymer chain
- the resin precursor composition according to the present embodiment contains, for example, the following component (b1-1).
- (B1-1) A polymer having two or more conjugated diene structures in the main chain of the polymer chain and a compound having a dienophile group having two or more functions.
- the resin precursor composition according to the present embodiment contains, for example, at least one of the following components (b3-1) to (b3-8).
- (B3-1) A polymer having two dienophile structures, a polymer having one dienophile structure at both ends of the polymer chain, and a polymer having more than two conjugated diene structures in the polymer chain.
- (B3-2) A polymer having two dienophile structures, a polymer having one dienophile structure at both ends of the polymer chain, and a polymer having more than two conjugated diene structures in the polymer chain.
- (B3-3) A polymer having two dienophile structures, a polymer having one dienophile structure at both ends of the polymer chain, and a polymer having more than two conjugated diene structures in the polymer chain.
- (B3-4) A polymer having two dienophile structures, a polymer having one dienophile structure at both ends of the polymer chain, and a main chain having no conjugated diene structure at both ends of the polymer chain. Polymer with more than two conjugated diene structures inside
- (B3-5) A polymer having two conjugated diene structures, one having one conjugated diene structure at both ends of the polymer chain, and one having more than two dienophile structures in the polymer chain.
- (B3-7) A polymer having two conjugated diene structures, a polymer having one conjugated diene structure at both ends of the polymer chain, and a polymer having more than two dienophile structures in the polymer chain. , A polymer having one dienophile structure at one end of the polymer chain, no dienophile structure at the other end, and two or more dienophile structures in the main chain.
- (B3-8) A polymer having two conjugated diene structures, a polymer having one conjugated diene structure at both ends of the polymer chain, and a polymer having no dienophile structure at both ends of the polymer chain and mainly Polymers with more than two dienophile structures in the chain
- the polymer contained in the resin precursor composition according to the present embodiment does not have at least two or more conjugated diene structures and dienophile structures at the ends of the polymer chains.
- the polymer chain is conjugated to at least one end of one end and the other end.
- the diene structure may not be bound, and the conjugated diene structure may not be bound to the end of the polymer chain.
- a composition containing the component (b2) in a polymer having two or more dielsophil structures, at least one end of the polymer chain and at least one end of the other end have a dielsophil structure. Does not have to be bound, and the Dielsophil structure may not be bound to the end of the polymer chain.
- conjugate is attached to at least one end of one end and the other end of the polymer chain.
- the dienophile structure is not bonded to at least one end of one end and the other end of the polymer chain.
- the conjugated diene structure and the dienophile structure may not be bound to the end of the polymer chain.
- the polymer contained in the resin precursor composition according to the present embodiment has at least one of a conjugated diene structure and a dienophile structure in the main chain of the polymer chain.
- one or more conjugated diene structures may be bonded to the main chain of the polymer chain. Further, all the conjugated diene structures may be bonded to the main chain of the polymer chain.
- one or more dienophile structures may be bonded to the main chain of the polymer chain. All the dienophile structures may be bound to the main chain of the polymer chain.
- one or more conjugated diene structures are bonded to the main chain of the polymer chain, and two conjugate diene structures are bonded.
- one or more dienophile structures may be bonded to the main chain of the polymer chain.
- the composition containing the component (b3) in the polymer having two or more conjugated diene structures, all the conjugated diene structures are bonded to the main chain of the polymer chain, and 2 In a polymer having one or more dienophile structures, all the dienophile structures may be bonded to the main chain of the polymer chain.
- the conjugated diene structure or the dienophile structure may be directly bonded to the main chain of the polymer chain, or the polymer may be directly bonded to the main chain of the polymer chain. It may be attached to the main chain of the chain.
- the polymer contained in the resin precursor composition according to the present embodiment does not have at least two or more conjugated diene structures and dienophile structures at the ends of the polymer chains.
- examples of the polymer having both a conjugated diene structure and a dienophile structure in one polymer chain include polymers having the following aspects.
- B4-1 A polymer in which a conjugated diene structure and a dienophile structure are not bonded to at least one end of one end and the other end of the polymer chain (b4-2) One end of the polymer chain One of the conjugated diene structure and the dienophile structure is bound to the molecule, and neither the conjugated diene structure nor the dienophile structure is bound to the other end of the polymer chain.
- a molecule to which at least one of the other structures is bonded
- b4-3 A polymer to which a conjugated diene structure and a dienophile structure are not bonded to the end of a polymer chain.
- the polymer contained in the resin precursor composition according to the present embodiment has at least one of a conjugated diene structure and a dienophile structure in the main chain of the polymer chain.
- a conjugated diene structure and a conjugated diene structure in the main chain of the polymer chain Any one or more of the dienophile structures may be bonded, or all the conjugated diene structures and the dienophile structures may be bonded to the main chain of the polymer chain.
- examples of the polymer having both a conjugated diene structure and a dienophile structure in one polymer chain include polymers having the following aspects.
- (B4-4) A polymer in which one dienophile structure is bonded to both ends of the polymer chain and at least one conjugated diene structure is bonded to the main chain of the polymer chain.
- the conjugated diene structure or the dienophile structure may be directly bonded to the main chain of the polymer chain, or the polymer may be directly bonded to the main chain of the polymer chain. It may be attached to the main chain of the chain.
- the bonds between the polymer chains in the resin formed when the resin precursor composition according to the present embodiment is used are not only the bonds between the ends of the polymer chains. That is, the bond between the polymer chains in the resin formed when the resin precursor composition according to the present embodiment is used is one of the conjugated diene structure and the dienophile structure bonded to the end of one polymer. , With one of the conjugated diene and dienophile structures attached to the main chain of the other polymer, or with the other of the conjugated diene and dienophile structures attached to the main chain of one polymer. It is also preferable to have at least one of a conjugated diene structure and a dienophile structure bonded to the main chain of the other polymer.
- the bonds are not made only between the ends of the polymer chains, three-dimensional cross-linking between the polymer chains occurs, and the solvent resistance of the resin can be easily improved. Further, even if the ends of the polymer chains are not bonded to each other, the three-dimensional cross-linking does not occur in the case of the bonds between the polymer chains having two reactive groups, and the polymer becomes a linear polymer. Therefore, the bonds between the polymer chains in the resin formed when the resin precursor composition according to the present embodiment is used are such that the polymers having two reaction points (reactive groups) in the polymer chains (for example). , It is preferable that the bond is not formed by the reaction of only polymers having a reactive group at the terminal.
- the bond between the polymer chains in the resin formed when the resin precursor composition according to the present embodiment is used may include a bond between the ends of the polymer chains.
- the first form of the polycarbonate polymer (hereinafter, also referred to as PC polymer) according to the present embodiment is a PC polymer having a repeating unit A alone represented by the following general formula (1). Alternatively, it has at least a repeating unit selected from the repeating unit A represented by the following general formula (1) and the repeating unit B represented by the following general formula (2), and is represented by the following general formula (1A). It can be obtained from at least one of a bischlorohomete oligomer represented by the following general formula (2A) and a bischlorohomete oligomer represented by the following general formula (2C) as a raw material.
- a bischlorohomete oligomer represented by the following general formula (2A) and a bischlorohomete oligomer represented by the following general formula (2C) as a raw material.
- Ar 33 is at least selected from the group consisting of the groups represented by the general formula (DE3), the general formula (DE5), and the general formula (DE8). It is one of the groups, and n 31 represents the average number of dimers. The average number of dimers n 31 is 1.0 or more and 10 or less.
- Ar 34 is a group represented by the general formula (UN11), and n 32 represents the average number of dimers. The average number of dimers n 32 is 1.0 or more and 10 or less.
- Ar 33 is at least one group selected from the group consisting of the groups represented by the general formula (DE3), the general formula (DE5), and the general formula (DE8).
- Ar 34 is a group represented by the general formula (UN11).
- n 33 and n 34 represent the average number of dimers, respectively. The total of the average number of dimers n 33 and n 34 is 1.0 or more and 10 or less. * Indicates the bonding position.
- Ar 33 and Ar 34 are different from each other.
- each repeating unit does not necessarily have to be continuous. Examples of the method for calculating the average number of dimers include the methods described in Examples described later.
- PC polymer has a repeating unit A containing a group represented by the general formula (DE3) having a conjugated diene structure, a polymer having two or more conjugated diene structures in a polymer chain. It becomes.
- the PC polymer having the unit B the one represented by the following general formula (100) is preferable.
- a represents the molar copolymer weight ratio in the repeating unit A
- b represents the molar copolymer weight ratio in the repeating unit B.
- a is [Ar 33 ] / ([Ar 33 ] + [Ar 34 ])
- b is [Ar 34 ] / ([Ar 33 ] + [Ar 34 ])
- repeat [Ar 33] represents the number of moles of repeating unit A containing a group represented by Ar 33 in the PC polymer
- [Ar 34] may include a group represented by Ar 34 in the PC polymer Represents the number of moles of unit B.
- each repeating unit is not always continuous.
- the PC polymer represented by the general formula (100) may be any of block copolymers, alternating copolymers, random copolymers and the like.
- the second form of the PC polymer according to the present embodiment has the general formula (DE4), the general formula (DE6), the general formula (DE7), and the general formula (DE9) as the chain end of the PC polymer. It has any of the structures represented by the general formula (DE12), the general formula (DE14), the general formula (DP1), the general formula (DP3), and the general formula (DP4).
- the PC polymer (100) does not have to contain Ar 33 , but in that case, the chain end needs to contain any of the above structures in total and contains two or more on average per molecule. be. However, when the polymer chain does not have two or more conjugated diene structures at the end, the PC polymer (100) preferably contains Ar 33. , On the other hand, in the case of a backbone containing the Ar 33, the total number of diene structure contained in the diene structure and the chain ends contained in the Ar 33 per molecule may be two or more. Further, it is preferable that the number of diene structures contained in Ar 33 per molecule is one or more.
- the chain end of the PC polymer according to the present embodiment is sealed with a monovalent aromatic group or a monovalent fluorine-containing aliphatic group within a range satisfying the requirements of the present application, in addition to the above-mentioned specific terminal group.
- the monovalent aromatic group may be a group containing an aliphatic group.
- the monovalent fluorine-containing aliphatic group may be a group containing an aromatic group. Further, at least one substituent selected from the group consisting of an alkyl group, a halogen atom, and an aryl group may be added to the monovalent aromatic group and the monovalent fluorine-containing aliphatic group.
- At least one substituent selected from the group consisting of an alkyl group, a halogen atom, and an aryl group may be further added to these substituents. Further, when there are a plurality of substituents, these substituents may be bonded to each other to form a ring.
- the monovalent aromatic group constituting the chain end preferably contains an aryl group having 6 to 12 ring-forming carbon atoms.
- Examples of such an aryl group include a phenyl group and a biphenyl group.
- Examples of the substituent added to the aromatic group and the substituent added to the alkyl group added to the aromatic group include halogen atoms such as a fluorine atom, a chlorine atom and a bromine atom.
- examples of the substituent added to the aromatic group include an alkyl group having 1 to 20 carbon atoms. This alkyl group may be a group to which a halogen atom is added as described above, or may be a group to which an aryl group is added.
- Examples of the monovalent fluorine-containing aliphatic group constituting the chain end include a monovalent group derived from a fluorine-containing alcohol.
- the fluorine-containing alcohol is preferably one in which a plurality of fluoroalkyl chains having 2 to 6 carbon atoms are linked to each other via an ether bond and the total number of fluorine atoms is 13 to 19.
- the total number of fluorine atoms is 13 or more, sufficient water repellency and oil repellency can be exhibited.
- the total number of fluorine atoms is 19 or less, the decrease in reactivity during polymerization can be suppressed, and at least one of the mechanical strength, surface hardness, heat resistance, etc. of the obtained PC polymer can be improved. ..
- the monovalent fluorine-containing aliphatic group a monovalent group derived from a fluorine-containing alcohol having two or more ether bonds is also preferable.
- a fluorine-containing alcohol By using such a fluorine-containing alcohol, the dispersibility of the PC polymer in the coating composition is improved, the abrasion resistance in the molded product or the electrophotographic photosensitive member is improved, and the surface lubricity and repellent after abrasion are improved. Can retain water and oil repellency.
- examples of the fluorine-containing alcohol include a fluorine-containing alcohol represented by the following general formula (30) or (31), a fluorine-containing alcohol such as 1,1,1,3,3,3-hexafluoro-2-propanol, and the like.
- a fluorine-containing alcohol via an ether bond represented by the following general formulas (32), (33), or (34) is also preferable.
- n1 is an integer of 1 to 12
- m1 is an integer of 1 to 12.
- n 31 is an integer of 1 to 10, preferably an integer of 5 to 8.
- n 32 is an integer from 0 to 5, preferably an integer from 0 to 3.
- n 33 is an integer from 1 to 5, preferably an integer from 1 to 3.
- n 34 is an integer of 1 to 5, preferably an integer of 1 to 3.
- n 35 is an integer from 0 to 5, preferably an integer from 0 to 3.
- R is CF 3 or F.
- the chain end of the PC polymer is a monovalent group derived from phenol represented by the following general formula (35) or the following general formula (36). ) Is preferably sealed with a monovalent group derived from the fluorine-containing alcohol.
- R 30 represents an alkyl group having 1 to 10 carbon atoms or a fluoroalkyl group having 1 to 10 carbon atoms
- p is an integer of 1 to 3.
- R f is a perfluoroalkyl group having 5 or more carbon atoms and 11 or more fluorine atoms, or a perfluoroalkyloxy group represented by the following general formula (37). show.
- R f2 is a linear or branched perfluoroalkyl group having 1 to 6 carbon atoms.
- mx is an integer from 1 to 3.
- the bischlorohomete oligomer compound represented by the general formula (1A) and the bischlorohomete oligomer represented by the general formula (2A) are used.
- Examples thereof include a production method in which at least one of the compounds, an organic solvent, an alkaline aqueous solution, and a monomer such as a bisphenol compound are used to mix an organic layer and an aqueous layer to carry out an interfacial polycondensation reaction.
- a monovalent carboxylic acid and its derivative, or a monovalent phenol can be used as the terminal encapsulant for producing the chain end.
- a fluorine-containing alcohol represented by the general formula (30) or (31), or 1,1,1,3,3,3-hexafluoro-2-propanol or the like As an end-capping agent that produces a chain end, a fluorine-containing alcohol represented by the general formula (30) or (31), or 1,1,1,3,3,3-hexafluoro-2-propanol or the like. A monovalent fluorine-containing alcohol is also preferably used. It is also preferable to use a fluorine-containing alcohol via an ether bond represented by the general formula (32), (33), or (34) as an end-capping agent for forming a chain end.
- the terminal encapsulant for forming the chain end is a monovalent phenol represented by the general formula (35) or the general formula (36) from the viewpoint of improving electrical characteristics and wear resistance. It is preferable to use the represented monovalent fluorine-containing alcohol.
- Examples of the monovalent phenol represented by the general formula (35) include p-tert-butyl-phenol, p-perfluorononylphenol, p-perfluorohexylphenol, p-tert-perfluorobutylphenol, and p-.
- Perfluorooctylphenol and the like are preferably used. That is, in the present embodiment, the chain end is a group consisting of p-tert-butyl-phenol, p-perfluorononylphenol, p-perfluorohexylphenol, p-tert-perfluorobutylphenol, and p-perfluorooctylphenol. It is preferably sealed with an end-capping agent selected from.
- Examples of the fluorine-containing alcohol via the ether bond represented by the general formula (36) include the following compounds. That is, it is preferable that the chain end of the present embodiment is sealed with an end sealant selected from any of the following fluorine-containing alcohols.
- the appropriate ratio of the end-capping agent is different depending on whether the Diels-Alder reactive functional group (conjugated diene or dienofil) is at the end or the main chain or side chain.
- conjugated diene or dienophile is contained at the terminal, the concentration of the crosslinkable reactive group and the molecular weight change in conjunction with each other depending on the fraction at the terminal.
- the molar percentage of the copolymerization composition of the diene or dienophile end group with respect to the total of the main chain and the terminal repeating unit is preferably 0.1 mol% or more and 67 mol% or less, more preferably 0.5 mol%. More than 50 mol% or less.
- the addition ratio of the end sealant is 67 mol% or less, the decrease in mechanical strength can be suppressed, and when it is 0.1 mol% or more, the effect of improving the characteristics by cross-linking can be obtained.
- the molar percentage of the copolymerization composition at the chain end with respect to the total of the main chain and the repeating unit at the end is preferably 0.05 mol% or more and 40 mol% or less, more preferably. Is 0.1 mol% or more and 20 mol% or less.
- the addition ratio of the end sealant is 40 mol% or less, the decrease in mechanical strength can be suppressed, and when it is 0.05 mol% or more, the decrease in moldability can be suppressed.
- the branching agent that can be used in the method for producing a PC polymer according to the present embodiment is not particularly limited, but specific examples of the branching agent include fluoroglucin, pyrogallol, 4,6-dimethyl-2,4,6. -Tris (4-hydroxyphenyl) -2-heptene, 2,6-dimethyl-2,4,6-tris (4-hydroxyphenyl) -3-heptene, 2,4-dimethyl-2,4,6-tris (4-Hydroxyphenyl) heptane, 1,3,5-tris (2-hydroxyphenyl) benzene, 1,3,5-tris (4-hydroxyphenyl) benzene, 1,1,1-tris (4-hydroxyphenyl) ) Etan, Tris (4-hydroxyphenyl) phenylmethane, 2,2-bis [4,54-bis (4-hydroxyphenyl) cyclohexyl] propane, 2,4-bis [2-bis (4-hydroxyphenyl)- 2-propyl]
- the addition ratio of these branching agents is 30 mol% or less in terms of the molar percentage of the copolymerization composition of the repeating unit A, the repeating unit B, and the chain end, or the molar percentage of the copolymer composition of the repeating unit A and the chain end. It is preferably 5 mol% or less, and more preferably 5 mol% or less.
- the addition ratio of the branching agent is 30 mol% or less, the decrease in moldability can be suppressed.
- examples of the acid binder include alkali metal hydroxides such as sodium hydroxide, potassium hydroxide, lithium hydroxide and cesium hydroxide, and alkaline soils such as magnesium hydroxide and calcium hydroxide.
- alkali metal weak acid salts such as metal hydroxides, sodium carbonate, potassium carbonate and calcium acetate, alkaline earth metal weak acid salts, and organic bases such as pyridine.
- Preferred acid binders for interfacial polycondensation are alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and calcium hydroxide, and alkaline earth metal hydroxides. In addition, these acid binders can also be used as a mixture.
- the ratio of the acid binder used may be appropriately adjusted in consideration of the stoichiometric ratio (equivalent) of the reaction. Specifically, 1 equivalent or an excess amount of the acid binder may be used per 1 mol of the total number of hydroxyl groups of the divalent phenol as the raw material, preferably 1 to 10 equivalents of the acid binder. good.
- the solvent used in the method for producing a PC polymer according to the present embodiment there is no problem as long as it shows a certain level of solubility in the obtained copolymer.
- the solvent include aromatic hydrocarbons such as toluene and xylene, methylene chloride, chloroform, 1,1-dichloroethane, 1,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2-trichloroethane, and the like.
- Halogenized hydrocarbons such as 1,1,1,2-tetrachloroethane, 1,1,2,2-tetrachloroethane, pentachloroethane and chlorobenzene, ketones such as cyclohexanone, acetone and acetophenone, tetrahydrofuran and 1,4-dioxane.
- Etc. such as ethers, are preferable.
- solvents may be used alone or in combination of two or more. Further, the interfacial polycondensation reaction may be carried out using two kinds of solvents which are immiscible with each other.
- the organic solvent used in the method for producing a PC polymer according to the present embodiment it is preferable to use an organic solvent that is substantially immiscible with water and can dissolve 5% by mass or more of the finally obtained polycarbonate copolymer. ..
- the organic solvent is preferably an organic solvent that is substantially immiscible with water and can dissolve 5% by mass or more of the finally obtained polycarbonate copolymer.
- the organic solvent "substantially immiscible with water” is composed of a uniform layer when water and the organic solvent are mixed in a composition range of 1: 9 to 9: 1 under normal temperature and pressure conditions. It is an organic solvent for which a solution (a solution in which neither a gelled substance nor an insoluble substance is found) cannot be obtained.
- the organic solvent "can dissolve 5% by mass or more of the finally obtained polycarbonate copolymer” is the solubility of the polycarbonate copolymer when measured under the conditions of a temperature of 20 to 30 ° C. and normal pressure.
- the "finally obtained polycarbonate polymer” is a polymer obtained through the polymerization step in the method for producing a polycarbonate polymer of the present embodiment, and is before crosslinking.
- examples of such an organic solvent include aromatic hydrocarbons such as toluene, ketones such as cyclohexanone, and halogenated hydrocarbons such as methylene chloride. Of these, methylene chloride is preferable because of its high solubility.
- the catalyst used in the method for producing the PC polymer of the present embodiment is not particularly limited, but for example, trimethylamine, triethylamine, tributylamine, N, N-dimethylcyclohexylamine, pyridine, N, N-diethylaniline, etc.
- Tertiary amines such as N, N-dimethylaniline, quaternary ammonium salts such as trimethylbenzylammonium chloride, triethylbenzylammonium chloride, tributylbenzylammonium chloride, trioctylmethylammonium chloride, tetrabutylammonium chloride, tetrabutylammonium bromide, Tetrabutylphosphonium chloride, tetrabutylphosphonium bromide and other quaternary phosphonium salts are suitable. Further, if necessary, a small amount of an antioxidant such as sodium sulfite or hydrosulfite salt may be added to the reaction system of the PC polymer of the present embodiment.
- an antioxidant such as sodium sulfite or hydrosulfite salt may be added to the reaction system of the PC polymer of the present embodiment.
- the coating liquid composition according to the present embodiment contains the resin precursor composition according to the present embodiment and an organic solvent.
- organic solvent consideration is given to the solubility of a material such as a resin precursor composition, the drying rate after molding, the effect of residual on the molded product, and the danger (fire or health hazard). However, it can be selected as appropriate.
- examples of the organic solvent according to the present embodiment include cyclic ethers (such as tetrahydrofuran (THF), dioxane, and dioxolane), cyclic ketones (such as cyclohexanone, cyclopentanone, and cycloheptanone), and aromatic hydrocarbons (toluene).
- ketones such as methyl ethyl ketone (MEK), and methyl isobutyl ketone (MIBK)
- halogenated hydrocarbons such as dichloromethane and chloroform
- esters ethyl acetate, isopropyl acetate, isobutyl acetate, etc.
- ethers such as ethylene glycol dimethyl ether and ethylene glycol monoethyl ether
- amides such as dimethyl fumarate (DMF), and dimethylacetamide (DMAc)
- aprotonic polar solvents dimethyl).
- the concentration of the resin precursor composition according to the present embodiment in the coating liquid composition according to the present embodiment may be any concentration as long as it has an appropriate viscosity according to the usage of the coating liquid composition. It is preferably 1% by mass or more and 40% by mass or less, more preferably 1% by mass or more and 35% by mass or less, and further preferably 5% by mass or more and 30% by mass or less. If it is 40% by mass or less, the viscosity does not become too high and the coatability is good. If it is 0.1% by mass or more, the viscosity can be maintained at an appropriate level, and a homogeneous film can be obtained. In addition, the drying time after coating is shortened, and the concentration is appropriate for easily achieving the target film thickness.
- the coating liquid composition may contain additives in addition to the resin precursor composition and the organic solvent according to the present embodiment.
- Additives include, for example, low molecular weight compounds, colorants (eg, dyes and pigments), functional compounds (eg, charge transport materials, electron transport materials, hole transport materials, and charge generators), fillings. Materials (eg, inorganic or organic fillers, fibers, cloths, and microparticles, etc.), antioxidants, UV absorbers, acid traps, and the like can be mentioned.
- the coating liquid composition may contain a resin other than the resin precursor composition according to the embodiment of the present invention. As these additives and other resins, known substances can be used as substances that can be blended with the resin precursor composition.
- the ratio of the resin precursor composition to the charge transporting substance in the coating liquid composition according to the present embodiment is from 20:80 to 80:20 in terms of mass ratio from the viewpoint of product performance. It is preferably in the range of 30:70 to 70:30, and more preferably in the range of 30:70 to 70:30.
- the resin precursor composition according to the present embodiment may be used alone or in combination of two or more.
- the coating liquid composition according to the present embodiment is usually preferably used for forming a photosensitive layer of a laminated electrophotographic photosensitive member.
- the photosensitive layer of the laminated electrophotographic photosensitive member preferably includes at least a charge generating layer and a charge transporting layer, and the coating liquid composition according to the present embodiment is preferably used for forming the charge transporting layer.
- the coating liquid composition according to the present embodiment is preferably used for forming the charge transporting layer.
- it can be used for forming a photosensitive layer of a single-layer type electrophotographic photosensitive member. It can also be used to form a protective layer for the photoconductor.
- the molded product according to the present embodiment contains the resin according to the present embodiment.
- the molded product according to this embodiment can be used for various purposes in addition to the use of the electrophotographic photosensitive member described later. For example, it can be suitably used for applications such as substrates such as electronic devices, insulating layers, protective layers, adhesive layers, conductive layers, and structural materials.
- the molded product according to the present embodiment can be produced by using the resin precursor composition according to the present embodiment.
- the resin precursor composition according to the present embodiment is used, either a wet molding method or a melt molding method can be applied as the molding method.
- a molded product is obtained by a wet molding method, (i) a method of molding at a temperature at which the cross-linking reaction proceeds, and (ii) a wet molded product is obtained at a temperature at which cross-linking does not substantially proceed, and then the solvent is removed.
- a method of raising the temperature to the temperature at which the reaction proceeds and cross-linking can be adopted. Any of these methods may be used.
- the above-mentioned coating liquid composition according to the present embodiment can be used.
- the cross-linking temperature can be appropriately set according to the target physical properties and the target application.
- the cross-linking method may be set by adjusting the type of the cross-linking functional group, the ratio of the conjugated diene and Diels-Alder, the functional group concentration, and the like according to the cross-linking temperature.
- the cross-linking temperature for an electrophotographic photosensitive member is usually preferably a wet-molded product obtained by wet molding and then cross-linked in a drying step, and the temperature is such that the functional low molecular weight compound does not deteriorate. Desired.
- the cross-linking temperature for the electrophotographic photosensitive member is preferably 60 ° C. or higher and 170 ° C. or lower, more preferably 80 ° C. or higher and 160 ° C. or lower, and further preferably 100 ° C. or higher and 150 ° C. or lower. When the cross-linking temperature exceeds 170 ° C., functional low molecular weight compounds such as charge transporting substances may be altered. If the cross-linking temperature is less than 60 ° C., drying does not proceed sufficiently or it takes a long time to dry, which is not preferable.
- the crosslinking temperature for electronic devices is preferably 60 ° C. or higher and 250 ° C. or lower, and more preferably 100 ° C. or higher and 200 ° C. or lower. If the cross-linking temperature exceeds 250 ° C., electronic components may fail or other organic materials may be decomposed. If the cross-linking temperature is less than 60 ° C., the cross-linking does not proceed sufficiently, or the viscosity of the material in which the cross-linking proceeds at such a low temperature increases due to the partial reaction progressing even in the coating liquid composition. There is a risk of stability problems.
- the cross-linking of the resin precursor composition can be carried out without adding a catalyst, a polymerization initiator or the like.
- substances such as catalysts and polymerization initiators may be added for the purpose of combined use with other cross-linking systems as long as the effects of the present embodiment are not impaired.
- the electrophotographic photosensitive member according to the present embodiment preferably contains the resin according to the present embodiment in the outermost layer.
- the electrophotographic photosensitive member according to the present embodiment has a substrate and a photosensitive layer provided on the substrate, and the photosensitive layer contains a resin according to the present embodiment.
- the electrophotographic photosensitive member of the present embodiment may be any electrophotographic photosensitive member as long as the resin according to the present embodiment is used in the photosensitive layer, as well as various known types of electrophotographic photosensitive member.
- the resin according to this embodiment may be used in any part of the photosensitive layer, but in order to fully exert the effect of this embodiment, it is used as a binder resin for a charge transfer substance in the charge transport layer. It is desirable to use it as a binder resin for a single photosensitive layer. Further, it is desirable to use it not only as a photosensitive layer but also as a surface protective layer. In the case of a multi-layer electrophotographic photosensitive member having two charge transport layers, it is preferable to use it for any one of the charge transport layers. In the electrophotographic photosensitive member of the present embodiment, the resin according to the present embodiment may be used alone or in combination of two or more. Further, if desired, a binder resin component such as other polycarbonate may be contained as long as the object of the present embodiment is not impaired. Further, an additive such as an antioxidant may be contained.
- the electrophotographic photosensitive member of this embodiment has a photosensitive layer on a conductive substrate.
- the charge transport layer may be laminated on the charge generation layer, or conversely, the charge generation layer may be laminated on the charge transport layer.
- it may be a photosensitive layer containing a charge generating substance and a charge transporting substance at the same time in one layer.
- a conductive or insulating protective film may be formed on the surface layer, if necessary.
- the conductive substrate material used for the electrophotographic photosensitive member of the present embodiment various materials such as known materials can be used, and specifically, aluminum, nickel, chromium, palladium, titanium, molybdenum, and indium. , Gold, platinum, silver, copper, zinc, brass, stainless steel, lead oxide, tin oxide, indium oxide, ITO (indium tin oxide: tin-doped indium oxide) or graphite, plates, drums, and sheets, vapor deposition, Glass, cloth, paper, and plastic films, sheets or seamless belts that have been conductively treated by coating by sputtering, coating, or the like, and metal drums that have been metal-oxidized by electrode oxidation or the like can be used.
- ITO indium tin oxide: tin-doped indium oxide
- the charge generation layer has at least a charge generation material.
- a layer of charge generation material is formed on the substrate which is the base thereof by vacuum deposition or sputtering method, or the charge generation material is bound on the substrate which is the base by using a binder resin. It can be obtained by forming a layer of resin.
- a method for forming the charge generation layer using the binder resin various methods such as a known method can be used. Usually, for example, a method in which a coating liquid composition in which a charge generating material is dispersed or dissolved with a binder resin in an appropriate solvent is applied onto a substrate as a predetermined base and dried to obtain a wet molded product is preferable.
- the charge generating material in the charge generating layer various known materials can be used. Specific compounds include selenium alone (eg, amorphous selenium and trigonal selenium, etc.), selenium alloys (eg, selenium-tellu, etc.), selenium compounds or selenium-containing compositions (eg, As 2 Se 3 and the like). ), Inorganic materials consisting of Group 12 and Group 16 elements of the periodic table (for example, zinc oxide and CdS-Se), oxide-based semiconductors (for example, titanium oxide), silicon-based materials (for example, amorphous silicon).
- Group 12 and Group 16 elements of the periodic table for example, zinc oxide and CdS-Se
- oxide-based semiconductors for example, titanium oxide
- silicon-based materials for example, amorphous silicon
- Metal-free phthalocyanine pigments eg, ⁇ -type metal-free phthalocyanine, and ⁇ -type metal-free phthalocyanine, etc.
- Metal phthalocyanine pigments eg, ⁇ -type copper phthalocyanine, ⁇ -type copper phthalocyanine, ⁇ -type copper phthalocyanine, ⁇ -type copper phthalocyanine
- X-type copper phthalocyanine A-type titanyl phthalocyanine, B-type titanyl phthalocyanine, C-type titanyl phthalocyanine, D-type titanyl phthalocyanine, E-type titanyl phthalocyanine, F-type titanyl phthalocyanine, G-type titanyl phthalocyanine, H-type titanyl phthalocyanine, K-type titanyl phthalocyanine , L-type titanyl phthalocyanine, M-type titanyl phthalocyanine, N-type titanyl phthalo
- These compounds can be used alone or in combination of two or more compounds as a charge generating substance.
- suitable charge generating substances include the charge generating substances specifically described in JP-A-11-172003.
- the charge transport layer can be obtained as a wet molded product by forming a layer formed by binding a charge transport substance with a binder resin on a substrate as a base.
- the binder resin for the charge generation layer and the charge transport layer is not particularly limited, and various known resins can be used. Specifically, for example, polystyrene, polyvinyl chloride, polyvinyl acetate, vinyl chloride-vinyl acetate copolymer, polyvinyl acetal, alkyd resin, acrylic resin, polyacrylonitrile, polycarbonate, polyurethane, epoxy resin, phenol resin, polyamide, etc.
- Polyketone polyacrylamide, butyral resin, polyester resin, vinylidene chloride-vinyl chloride copolymer, methacrylic resin, styrene-butadiene copolymer, vinylidene chloride-acrylonitrile copolymer, vinyl chloride-vinyl acetate-maleic anhydride copolymer , Silicon resin, Silicon alkyd resin, Phenol-formaldehyde resin, Styrene-Alkid resin, Melamine resin, Polyether resin, Benzoguanamine resin, Epoxy acrylate resin, Urethane acrylate resin, Poly-N-Vinylcarbazole, Polyvinyl butyral, Polyvinylformal, Polysulfone , Casein, gelatin, polyvinyl alcohol, ethyl cellulose, nitrocellulose, carboxy-methylcellulose, vinylidene chloride polymer latex, acrylonitrile-butadiene copolymer, vinyltoluene-
- a coating liquid composition in which the charge transport substance is dispersed or dissolved in an appropriate solvent together with the PC polymer of the present embodiment is provided as a predetermined method.
- a method of applying it on a substrate as a base and drying it to obtain a wet molded product is preferable.
- the blending ratio of the charge transport substance used for forming the charge transport layer and the PC polymer is preferably in the range of 20:80 to 80:20, more preferably in the range of 30:70 to 70:30 in terms of mass ratio. be.
- the PC polymer of the present embodiment can be used alone or in combination of two or more. Further, it is also possible to use another binder resin in combination with the PC polymer of the present embodiment as long as the object of the present invention is not impaired.
- the thickness of the charge transport layer thus formed is usually about 5 ⁇ m or more and 100 ⁇ m or less, preferably 10 ⁇ m or more and 50 ⁇ m or less, and more preferably 15 ⁇ m or more and 40 ⁇ m or less. When this thickness is 5 ⁇ m or more, the initial potential does not decrease, and when it is 100 ⁇ m or less, deterioration of electrophotographic characteristics can be prevented.
- the charge transporting substance that can be used together with the PC polymer of the present embodiment various known compounds can be used.
- Examples of such compounds include carbazole compounds, indol compounds, imidazole compounds, oxazole compounds, pyrazole compounds, oxaziazole compounds, pyrazoline compounds, thiadiazol compounds, aniline compounds, hydrazone compounds, aromatic amine compounds and aliphatic amine compounds.
- Stilben compounds Fluorenone compounds, butadiene compounds, quinone compounds, quinodimethane compounds, thiazole compounds, triazole compounds, imidazolone compounds, imidazolidine compounds, bisimidazolidine compounds, oxazolone compounds, benzothiazole compounds, benzimidazole compounds, quinazoline compounds, benzofuran compounds , Aclysine compound, phenazine compound, poly-N-vinylcarbazole, polyvinylpyrene, polyvinylanthracene, polyvinylacridin, poly-9-vinylphenylanthracene, pyrene-formaldehyde resin, ethylcarbazole resin, or the main chain or side chain of these structures.
- the polymer contained in the above is preferably used. These compounds may be used alone or in combination of two or more. Among these charge-transporting substances, the compounds specifically exemplified in JP-A-11-172003 and the charge-transporting substances represented by the following structures are particularly preferably used.
- the resin precursor composition according to the present embodiment as a binder resin for at least one of the charge generation layer, the charge transport layer, and the surface protection layer. be.
- an undercoat layer as is normally used can be provided between the conductive substrate and the photosensitive layer.
- the undercoat layer includes, for example, fine particles (eg, titanium oxide, aluminum oxide, zirconia, titanic acid, zirconic acid, lanthanum lead, titanium black, silica, lead titanate, barium titanate, tin oxide, indium oxide, and the like. (Silicon oxide, etc.), polyamide resin, phenol resin, casein, melamine resin, benzoguanamine resin, polyurethane resin, epoxy resin, cellulose, nitrocellulose, polyvinyl alcohol, polyvinyl butyral resin, and other components can be used.
- the binder resin may be used, or the resin precursor composition according to the present embodiment may be used.
- These fine particles and resin can be used alone or in admixture. When used as a mixture of these, it is preferable to use the inorganic fine particles and the resin in combination because a film having good smoothness is formed.
- the thickness of the undercoat layer is 0.01 ⁇ m or more and 10 ⁇ m or less, preferably 0.1 ⁇ m or more and 7 ⁇ m or less. When this thickness is 0.01 ⁇ m or more, the undercoat layer can be uniformly formed, and when it is 10 ⁇ m or less, deterioration of electrophotographic characteristics can be suppressed.
- a known blocking layer that is usually used can be provided between the conductive substrate and the photosensitive layer.
- a resin of the same type as the binder resin can be used. Moreover, you may use the resin precursor composition which concerns on this embodiment.
- the thickness of this blocking layer is 0.01 ⁇ m or more and 20 ⁇ m or less, preferably 0.1 ⁇ m or more and 10 ⁇ m or less. When this thickness is 0.01 ⁇ m or more, the blocking layer can be uniformly formed, and when it is 20 ⁇ m or less, deterioration of electrophotographic characteristics can be suppressed.
- a protective layer may be laminated on the photosensitive layer.
- a resin of the same type as the binder resin can be used for this protective layer. Further, it is particularly preferable to use the resin precursor composition according to the present embodiment.
- the thickness of this protective layer is 0.01 ⁇ m or more and 20 ⁇ m or less, preferably 0.1 ⁇ m or more and 10 ⁇ m or less.
- the protective layer contains the charge generating substance, the charge transporting substance, the additive, the metal and its oxide, the nitride, or a conductive material such as a salt, an alloy, carbon black, and an organic conductive compound. May be.
- the charge generating layer and the charge transporting layer are provided with a binder, a plasticizer, a curing catalyst, a fluidity imparting agent, and pinholes as long as the effects of the present invention are not lost.
- a control agent, a spectrosensitive sensitizer (infectious agent), and the like may be added.
- various chemical substances, antioxidants, surfactants, curl inhibitors, leveling agents, etc. are added for the purpose of preventing an increase in residual potential, a decrease in charge potential, and a decrease in sensitivity with repeated use. Agents can be added.
- binder examples include silicone resin, polyamide resin, polyurethane resin, polyester resin, epoxy resin, polyketone resin, polycarbonate copolymer, polystyrene resin, polymethacrylate resin, polyacrylamide resin, polybutadiene resin, polyisoprene resin, and melamine.
- thermosetting resin and a photocurable resin
- the resin is electrically insulating and can form a film in a normal state, and is not particularly limited as long as it does not impair the effects of the present embodiment.
- plasticizer examples include biphenyl, biphenyl chloride, o-terphenyl, halogenated paraffin, dimethylnaphthalene, dimethylphthalate, dibutylphthalate, dioctylphthalate, diethyleneglycolphthalate, triphenylphosphate, diisobutyladipate, and dimethylseva.
- plasticizer examples include cate, dibutylsevacate, butyl laurate, methylphthalyl ethylglycolate, dimethylglycolphthalate, methylnaphthalene, benzophenone, polypropylene, polystyrene, and fluorohydrocarbons.
- the curing catalyst include methanesulfonic acid, dodecylbenzenesulfonic acid, dinonylnaphthalenedisulfonic acid, and the like
- examples of the fluidity-imparting agent include modaflow and acronal 4F
- examples of the pinhole control agent include benzoin and dimethylphthalate.
- a triphenylmethane dye for example, methyl violet, crystal violet, night blue, and Victoria blue
- an acridin dye for example, erythrosin.
- Thiadine Dyes eg, Methylene Blue, and Methylene Green, etc.
- Oxazine Dyes Capri Blue, and Meldra Blue, etc.
- Cyanine Dyes, Melosinine Dyes, Styryl Dyes, Pyrylium salt dyes, thiopyrilium salt dyes and the like are suitable.
- An electron-accepting substance can be added to the photosensitive layer for the purpose of improving sensitivity, reducing residual potential, reducing fatigue during repeated use, etc., as long as the effects of the present invention are not lost.
- Specific examples thereof include succinic anhydride, maleic anhydride, dibromomaleic anhydride, phthalic anhydride, tetrachlorophthalic anhydride, tetrabromophthalic anhydride, 3-nitrohydride phthalic acid, and 4-nitrohydride phthalic acid.
- These compounds may be added to either the charge generating layer or the charge transporting layer, and the blending ratio thereof is based on the case where the amount of the charge generating substance or the charge transporting substance is 100 parts by mass within a range that does not lose the effect of the present invention. It is 0.01 part by mass or more and 200 parts by mass or less, preferably 0.1 parts by mass or more and 50 parts by mass or less.
- ethylene tetrafluoride resin ethylene trifluoride resin, ethylene tetrafluoride propylene hexafluoride resin, vinyl fluoride resin, vinylidene fluoride resin, ethylene difluoride dichloride resin and These copolymers, fluorine-based graft polymers, and the like may be used as long as the effects of the present invention are not lost.
- the blending ratio of these surface modifiers is 0.1% by mass or more and 60% by mass or less, preferably 5% by mass or more and 40% by mass or less, with respect to the binder resin as long as the effects of the present invention are not lost. If the blending ratio is 0.1% by mass or more, surface modification such as surface durability and reduction in surface energy is sufficient, and if it is 60% by mass or less, the electrophotographic characteristics are not deteriorated.
- antioxidant for example, a hindered phenol-based antioxidant, an aromatic amine-based antioxidant, a hindered amine-based antioxidant, a sulfide-based antioxidant, an organic phosphoric acid-based antioxidant, and the like are preferable.
- the blending ratio of these antioxidants is usually 0.01% by mass or more and 10% by mass or less, preferably 0.1% by mass or more and 2% by mass, based on the charge transporting substance, as long as the effects of the present invention are not lost. It is as follows.
- the compounds of the general chemical formulas [Chemical 94] to [Chemical 101] described in the specification of JP-A-11-172003 are suitable. These antioxidants may be used alone or in admixture of two or more, and these may be added to the photosensitive layer, the surface protective layer, the undercoat layer, and the blocking layer. You may.
- the solvent used in forming at least one of the charge generation layer and the charge transport layer include, for example, aromatic solvents (for example, benzene, toluene, xylene, and chloroform), ketones (for example, for example, chlorobenzene, etc.).
- aromatic solvents for example, benzene, toluene, xylene, and chloroform
- ketones for example, for example, chlorobenzene, etc.
- alcohols eg, methanol, ethanol, and isopropanol, etc
- the photosensitive layer of the single-layer electrophotographic photosensitive member is easily formed by applying the resin precursor composition according to the present embodiment as a binder resin using the above-mentioned charge generating substance, charge transporting substance, and additive. be able to. Further, as the charge transporting substance, it is preferable to add at least one of the above-mentioned hole transporting substance and electron transporting substance.
- the electron-transporting substance the electron-transporting substance exemplified in JP-A-2005-139339 can be preferably applied.
- each layer can be performed using various coating devices such as known devices, specifically, for example, an applicator, a spray coater, a bar coater, a tip coater, a roll coater, a dip coater, and a doctor blade. Can be done.
- the thickness of the photosensitive layer in the electrophotographic photosensitive member is 5 ⁇ m or more and 100 ⁇ m or less, preferably 8 ⁇ m or more and 50 ⁇ m or less. When this is 5 ⁇ m or more, it is possible to prevent the initial potential from being lowered, and when it is 100 ⁇ m or less, the electron It is possible to suppress deterioration of photographic characteristics.
- the ratio of the charge generating substance: resin precursor composition used in the production of the electrophotographic photosensitive member is preferably in the range of 20:80 to 80:20 by mass ratio, and in the range of 30:70 to 70:30. More preferably.
- the electrophotographic photosensitive member Since the electrophotographic photosensitive member thus obtained has a crosslinked resin composed of the resin precursor composition according to the present embodiment as a binder resin in the photosensitive layer, it has solvent resistance and durability (wear resistance). ), And also has excellent electrical characteristics (electrophotographic characteristics), and is a photoconductor that maintains excellent electrophotographic characteristics for a long period of time.
- the electrophotographic photosensitive member includes various electronic devices such as copiers (monochrome, multicolor, full color, analog, digital), printers (laser, LED, liquid crystal shutter), facsimiles, plate making machines, and devices having these multiple functions. It is preferably used in the photographic field.
- the method for producing an electrophotographic photosensitive member according to the present embodiment is a step of applying the coating liquid composition according to the present embodiment to a conductive substrate by a wet molding method, and heating the coating liquid composition in the coating liquid composition.
- the process comprises a step of removing the organic solvent and a step of performing a cross-linking reaction of the resin precursor composition in the coating liquid composition by simultaneously or continuously heating the heating in the step of removing the organic solvent.
- the coating thickness of the coating liquid composition can be appropriately set according to the thickness of the photosensitive layer of the electrophotographic photosensitive member according to the present embodiment.
- the step of removing the organic solvent it can be appropriately set according to the type of the organic solvent in the coating liquid composition according to the present embodiment.
- the heating temperature is the same as the cross-linking temperature for the electrophotographic photosensitive member in the molded product according to the present embodiment.
- methylene chloride was distilled off until it reached a predetermined concentration.
- 210 mL of pure water, 1.2 g of concentrated hydrochloric acid, and 450 mg of hydrosulfite were added and washed.
- washing with 210 mL of pure water was repeated 5 times to obtain a methylene chloride solution of a bisphenol Z oligomer having a chlorohomate group at the molecular terminal.
- the chlorohomate concentration of the obtained solution was 1.12 mol / L
- the solid matter concentration was 0.225 kg / L
- the average number of dimers was 1.03.
- the obtained raw material is referred to as Z-CF.
- M1 is calculated by the following formula.
- M1 (268 ⁇ (366 ⁇ (366 + 108)) + 214 ⁇ (108 ⁇ (366 + 108)) +124.9 "124.9" in the calculation formula of M1 is a molecular weight increment when two hydrogen atoms of the monomer used are eliminated and two carbon atoms, two oxygen atoms, and two chlorine atoms are increased.
- Ar X1 is a divalent group.
- the divalent group represented by the following general formula (10) corresponds to Ar X1.
- Ar 33 corresponds to Ar X1 and n 31 corresponds to n X.
- Ar 34 corresponds to Ar X1 and n 32 corresponds to n X.
- a solution prepared by dissolving 93.8 g (929 mmol) of triethylamine in 256 mL of methylene chloride was added dropwise in a temperature range of 16 ° C to 19 ° C. Next, after stirring for 140 minutes, methylene chloride was distilled off until it reached a predetermined concentration. To the residual liquid, 1100 mL of pure water, 2.4 g of concentrated hydrochloric acid, and 450 mg of hydrosulfite were added and washed.
- methylene chloride was distilled off until it reached a predetermined concentration.
- 1100 mL of pure water, 2.4 g of concentrated hydrochloric acid, and 450 mg of hydrosulfite were added and washed.
- washing with 210 mL of pure water was repeated 5 times to obtain a methylene chloride solution of a bisphenol Z oligomer having a chlorohomate group at the molecular terminal and 3,3'-dimethyl-4,4'-dihydroxybiphenyl oligomer.
- the chlorohomate concentration of the obtained solution was 0.52 mol / L, the solid matter concentration was 0.089 kg / L, and the average number of dimers was 1.01.
- the obtained raw material is referred to as OCBP-CF.
- a solution prepared by dissolving 93.8 g (929 mmol) of triethylamine in 256 mL of methylene chloride was added dropwise in a temperature range of 16 ° C to 19 ° C. Next, after stirring for 140 minutes, methylene chloride was distilled off until it reached a predetermined concentration. To the residual liquid, 1100 mL of pure water, 2.4 g of concentrated hydrochloric acid, and 450 mg of hydrosulfite were added and washed.
- the PC polymer (PC-1) thus obtained was dissolved in methylene chloride to prepare a solution having a concentration of 0.5 g / dL, and the reduced viscosity [ ⁇ sp / C] at 20 ° C. was measured. It was 1.06 dL / g.
- the reduced viscosity was measured with a Ubberode improved viscometer (RM type) for automatic viscosity using an automatic viscosity measuring device VMR-042 manufactured by Rigosha.
- the 1 H-NMR spectrum was measured by a nuclear magnetic resonance apparatus JNM-ECZ400S manufactured by JEOL Ltd. 1
- the measurement conditions of the 1 H-NMR spectrum are as follows.
- concentration of the conjugated diene group (anthracene skeleton) is 0.71 mmol / g.
- a 3,3'-dimethyl-4,4'-dihydroxybiphenyl solution prepared in this solution (solution preparation method: 60 mL of a 2.5 mol / L potassium carbonate aqueous solution) (20.9 g of potassium carbonate) was prepared, cooled to room temperature or lower, and then 0.1 g of hydrosulfite and 7.3 g of 3,3'-dimethyl-4,4'-dihydroxybiphenyl were added as antioxidants. The whole amount was added, 2.7 mL of an aqueous triethylamine solution (7 vol%) was added while stirring, and stirring was continued for 3 hours. The obtained reaction mixture was diluted with 0.5 L of methylene chloride and 0.1 L of water and washed.
- PC-2 PC polymer having the following structure.
- PC polymer (PC-2) The PC polymer (PC-2) thus obtained was dissolved in methylene chloride to prepare a solution having a concentration of 0.5 g / dL, and the reduced viscosity [ ⁇ sp / C] at 20 ° C. was measured. It was 0.23 dL / g.
- the structure and composition of the obtained PC-2 were analyzed by 1H-NMR spectrum, it was confirmed that the PC polymer consisted of the following repeating units, the number of repeating units, and the composition.
- concentration of dielsophil group (maleimide group) is 0.39 mmol / g.
- PC polymer (PC-3) was dissolved in methylene chloride to prepare a solution having a concentration of 0.5 g / dL, and the reduced viscosity [ ⁇ sp / C] at 20 ° C. was measured. It was 1.08 dL / g.
- the structure and composition of the obtained PC-3 were analyzed by 1 H-NMR spectrum, it was confirmed that the PC polymer consisted of the following repeating units, the number of repeating units, and the composition.
- concentration of the conjugated diene group (anthracene skeleton) is 0.39 mmol / g.
- PC polymer (PC-4) was dissolved in methylene chloride to prepare a solution having a concentration of 0.5 g / dL, and the reduced viscosity [ ⁇ sp / C] at 20 ° C. was measured. It was 0.95 dL / g.
- the structure and composition of the obtained PC-4 were analyzed by 1 H-NMR spectrum, it was confirmed that the PC polymer consisted of the following repeating units, the number of repeating units, and the composition.
- concentration of the conjugated diene group (anthracene skeleton) is 1.44 mmol / g.
- PC polymer (PC-5) was dissolved in methylene chloride to prepare a solution having a concentration of 0.5 g / dL, and the reduced viscosity [ ⁇ sp / C] at 20 ° C. was measured. It was 0.95 dL / g.
- the structure and composition of the obtained PC-5 were analyzed by 1 H-NMR spectrum, it was confirmed that the PC polymer consisted of the following repeating units, the number of repeating units, and the composition.
- concentration of the conjugated diene group (anthracene skeleton) is 1.44 mmol / g.
- PC-6 having the following structure was obtained in the same manner as in Synthesis Example 1.
- PC-6 The PC polymer (PC-6) thus obtained was dissolved in methylene chloride to prepare a solution having a concentration of 0.5 g / dL, and the reduced viscosity [ ⁇ sp / C] at 20 ° C. was measured. It was 1.25 dL / g.
- the structure and composition of the obtained PC-6 were analyzed by 1 H-NMR spectrum, it was confirmed that the PC polymer consisted of the following repeating units, the number of repeating units, and the composition.
- concentration of the conjugated diene group (anthracene skeleton) is 0.82 mmol / g.
- PC-7 (Specification of PC polymer)
- the PC polymer (PC-7) thus obtained was dissolved in methylene chloride to prepare a solution having a concentration of 0.5 g / dL, and the reduced viscosity [ ⁇ sp / C] at 20 ° C. was measured. It was 0.66 dL / g.
- the structure and composition of the obtained PC-7 were analyzed by 1 H-NMR spectrum, it was confirmed that the PC polymer consisted of the following repeating units, the number of repeating units, and the composition.
- concentration of the conjugated diene group (anthracene skeleton) is 0.74 mmol / g.
- concentration of the Dielsophil group maleimide skeleton is 0.082 mmol / g.
- PC polymer (PC-8) The PC polymer (PC-8) thus obtained was dissolved in methylene chloride to prepare a solution having a concentration of 0.5 g / dL, and the reduced viscosity [ ⁇ sp / C] at 20 ° C. was measured. It was 1.04 dL / g.
- the structure and composition of the obtained PC-8 were analyzed by 1 H-NMR spectrum, it was confirmed that the PC polymer consisted of the following repeating units, the number of repeating units, and the composition.
- concentration of the conjugated diene group (anthracene skeleton) is 0.46 mmol / g.
- PC polymer (PC-9) The PC polymer (PC-9) thus obtained was dissolved in methylene chloride to prepare a solution having a concentration of 0.5 g / dL, and the reduced viscosity [ ⁇ sp / C] at 20 ° C. was measured. It was 1.07 dL / g.
- the structure and composition of the obtained PC-9 were analyzed by 1 H-NMR spectrum, it was confirmed that the PC polymer consisted of the following repeating units, the number of repeating units, and the composition.
- concentration of the conjugated diene group (anthracene skeleton) is 0.39 mmol / g.
- the measurement probe After the value of the oxygen concentration in the gas phase read in the DO mode of the dissolved oxygen meter (DO meter MODEL B-506 manufactured by Iijima Electronics Co., Ltd.) becomes 0.5 mg / L or less, the measurement probe is immersed in the reaction solution. The oxygen concentration in the solution was measured, and it was confirmed that the reading value was 0.5 mg / L or less, which was the same as in the gas phase.
- a 2.3 N aqueous potassium carbonate solution (prepared by dissolving 1.26 g of potassium carbonate in ion-exchanged water (4 mL) and adding 50 mg of hydrosulfite sodium).
- PC-10) having the following structure.
- PC-10 (Specification of PC polymer)
- the PC polymer (PC-10) thus obtained was dissolved in methylene chloride to prepare a solution having a concentration of 0.5 g / dL, and the reduced viscosity [ ⁇ sp / C] at 20 ° C. was measured. It was 1.56 dL / g.
- the structure and composition of the obtained PC-10 were analyzed by 1 H-NMR spectrum, it was confirmed that the PC polymer consisted of the following repeating units, the number of repeating units, and the composition.
- the furan group concentration is 1.89 mmol / g.
- the measurement probe After the value of the oxygen concentration in the gas phase read in the DO mode of the dissolved oxygen meter (DO meter MODEL B-506 manufactured by Iijima Electronics Co., Ltd.) becomes 0.5 mg / L or less, the measurement probe is immersed in the reaction solution. The oxygen concentration in the solution was measured, and it was confirmed that the reading value was 0.5 mg / L or less as in the gas phase. After cooling to a temperature of 10 ° C. in the reactor, a 1.6 N aqueous potassium carbonate solution (prepared by dissolving 1.07 g of potassium carbonate in ion-exchanged water (5 mL) and adding 50 mg of hydrosulfite sodium).
- the obtained reaction mixture was diluted with 200 mL of methylene chloride and 50 mLL of water whose oxygen concentration was separately reduced to 0.1 mg / L or less by nitrogen substitution in a nitrogen atmosphere, and washed.
- the lower layer was separated, and further washed once with 100 mL of water, once with 100 mL of 0.03N hydrochloric acid, and three times with 100 mL of water.
- the obtained methylene chloride solution was added dropwise to methanol under stirring, and the obtained reprecipitate was filtered and dried to obtain a PC polymer (PC-11) having the following structure.
- PC polymer (PC-1) The PC polymer (PC-1) thus obtained was dissolved in methylene chloride to prepare a solution having a concentration of 0.5 g / dL, and the reduced viscosity [ ⁇ sp / C] at 20 ° C. was measured. It was 0.72 dL / g.
- the structure and composition of the obtained PC-11 were analyzed by 1 H-NMR spectrum, it was confirmed that the PC polymer consisted of the following repeating units, the number of repeating units, and the composition.
- the anthracene group concentration is 0.49 mmol / g.
- PC- PC polymer having the following structure is the same as in Synthesis Example 8 except that the 1N potassium hydroxide aqueous solution is changed to 12 mL (potassium hydroxide 1.4 g) and the amount of triethylamine used is changed to 0.3 mL. 12) was obtained.
- PC polymer (PC-12) was dissolved in methylene chloride to prepare a solution having a concentration of 0.5 g / dL, and the reduced viscosity [ ⁇ sp / C] at 20 ° C. was measured. It was 1.37 dL / g.
- the structure and composition of the obtained PC-12 were analyzed by 1 H-NMR spectrum, it was confirmed that the PC polymer consisted of the following repeating units, the number of repeating units, and the composition.
- concentration of the conjugated diene group (anthracene skeleton) is 0.46 mmol / g.
- the PC polymer (PAR-1) thus obtained was dissolved in methylene chloride to prepare a solution having a concentration of 0.5 g / dL, and the reduced viscosity [ ⁇ sp / C] at 20 ° C. was measured. It was 0.27 dL / g.
- the structure and composition of the obtained PAR-1 were analyzed by 1 H-NMR spectrum, it was confirmed that the PAR polymer consisted of the following repeating units, the number of repeating units, and the composition.
- concentration of the conjugated diene group (anthracene skeleton) is 0.52 mmol / g.
- Example 1 ⁇ Preparation of a coating composition consisting of a polycarbonate having a conjugated diene group and a polycarbonate having a Dielsophil group, and preparation of a crosslinked resin film> 1.5 g of PC-1 and 0.3 g of PC-2 were weighed in a sample tube with a screw cap and dissolved in 10 mL of tetrahydrofuran to obtain a coating composition.
- the obtained coating liquid composition was cast and formed on a polyimide film having a thickness of 50 ⁇ m using an applicator having a gap of 200 ⁇ m. After air-drying for 1 hour, the mixture was treated with a vacuum dryer at a temperature of 50 ° C. for 16 hours to remove the solvent to obtain a precursor film.
- the obtained precursor film was heated in a vacuum drier (decompression degree is 1 to 100 Pa) at a temperature of 200 ° C. for 3 hours for cross-linking treatment to obtain a resin film.
- Example 2 ⁇ Preparation of a coating composition for a charge transport layer composed of a polycarbonate having a conjugated diene group, a polycarbonate having a dienophil group, and a charge transport substance, and preparation of a crosslinked resin film>
- PC-1 polycarbonate having a conjugated diene group
- PC-2 polycarbonate having a dienophil group
- CTM-1 charge transporter
- a liquid composition was obtained.
- the obtained coating liquid composition was cast and formed on a polyimide film having a thickness of 50 ⁇ m using an applicator having a gap of 200 ⁇ m.
- the mixture was treated with a vacuum dryer at a temperature of 50 ° C. for 16 hours to remove the solvent to obtain a precursor film.
- the obtained precursor film was heated in a vacuum drier (decompression degree is 1 to 100 Pa) at a temperature of 150 ° C. for 3 hours and crosslinked to obtain a resin film.
- Example 2 The coating composition and resin film (for wear test and electrical characteristics) were the same as in Example 2 except that PC-2 was not used in Example 2 and the amount of PC-1 used was changed to 1.5 g. For evaluation) was obtained.
- Example 100 A resin film (for wear test) was obtained in the same manner as in Example 1 except that PC-1 and PC-2 were not used in Example 1 and a polycarbonate resin having the following structure (used amount: 1.5 g) was used. rice field.
- Comparative Example 101 The coating composition and resin were the same as in Example 2 except that PC-1 and PC-2 were not used in Example 2 and the polycarbonate resin (amount used: 1.5 g) used in Comparative Example 100 was used. Films (for wear testing and for electrical property evaluation) were obtained.
- An electrophotographic photosensitive member was produced in which an aluminum plate having a thickness of 100 ⁇ m was used as a conductive substrate, and a charge generating layer and a charge transporting layer were sequentially laminated on the surface of the aluminum plate to form a laminated photosensitive layer.
- 0.5 parts by mass of Y-type oxotitanium phthalocyanine was used as the charge generating substance, and 0.5 parts by mass of butyral resin was used as the binder resin. These were added to 19 parts by mass of THF of the solvent, dispersed by a ball mill, the dispersion liquid was coated on the surface of the conductive substrate film with a bar coater, and dried at 70 ° C.
- the coating liquid composition for the charge transport layer the coating liquid composition obtained in the same manner except that the amount of CTM-1 used was changed to 0.75 g in Example 2 was used with an applicator having a gap of 200 ⁇ m. It was applied onto the charge generation layer and dried at a temperature of 50 ° C. for 8 hours and then at a temperature of 100 ° C. for 8 hours under reduced pressure (the degree of reduced pressure was 1 to 100 Pa) to form a charge transport layer having a film thickness of about 30 ⁇ m. The obtained photoconductor film was heated at a temperature of 150 ° C. for 3 hours to obtain a photoconductor.
- the obtained electrophotographic photosensitive film was attached to an aluminum drum having a diameter of 60 mm, and the electrophotographic characteristics were evaluated using an electrostatic charge test device CYNTHIA54IM (manufactured by Gentec Co., Ltd.) in EV mode.
- the initial charge amount was ⁇ 750 V.
- the obtained results are shown in FIG.
- the coating liquid compositions obtained in Comparative Example 2 and Comparative Example 101 were also evaluated for the light attenuation characteristics of the surface potential in the same manner as described above. The obtained results are shown in FIG.
- diene represented by the following formula (MI-BizA)
- MI-BizA 2,2-bis [ 0.56 g of 4- (4-maleimidephenoxy) phenyl] propane (hereinafter referred to as MI-BizA) was weighed in a sample tube with a screw cap and dissolved in 10 mL of tetrahydrofuran to obtain a coating composition. ..
- the obtained coating liquid composition was cast and formed on a polyimide film having a thickness of 50 ⁇ m using an applicator having a gap of 200 ⁇ m.
- the mixture was treated with a vacuum dryer at a temperature of 50 ° C. for 16 hours to remove the solvent to obtain a precursor film.
- the obtained precursor film was heated in a vacuum drier (decompression degree is 1 to 100 Pa) at a temperature of 200 ° C. for 3 hours for cross-linking treatment to obtain a resin film.
- the obtained resin film was evaluated for solvent resistance (methylene chloride solubility) and abrasion resistance by the above-mentioned method. The results obtained are shown in Table 2.
- Example 4 to 12 A resin film was obtained in the same manner as in Example 3 except that the conjugated diene, the dienophile, and the charge transporting substance were as shown in Table 2 below, and the heating conditions were as shown in Table 2 below. Then, the obtained resin film was evaluated for solvent resistance and abrasion resistance by the above-mentioned method. The results obtained are shown in Table 2.
- the charge transport substance (CTM-2) is a mixture shown below.
- Example 3-1 A resin film was obtained in the same manner as in Example 3 except that MI-BisA was not used in Example 3 and the heating conditions were changed to 100 ° C. for 3 hours. Then, the obtained resin film was evaluated for solvent resistance and abrasion resistance by the above-mentioned method. The results obtained are shown in Table 2.
- Examples 13 to 17 The same as in Example 3 except that the conjugated diene, the dienophile, and the charge transport material were as shown in Table 3 below, the heating conditions were as shown in Table 3 below, and the number of repetitions of the wear test was changed to 800 times. To obtain a resin film. Then, the obtained resin film was evaluated for solvent resistance and abrasion resistance by the above-mentioned method. The results obtained are shown in Table 3.
- Comparative Example 3- except that the conjugated diene, the dienophile, and the charge transport material were as shown in Table 3 below, the heating conditions were as shown in Table 3 below, and the number of repetitions of the wear test was changed to 800 times.
- a resin film was obtained in the same manner as in 1. Then, the obtained resin film was evaluated for solvent resistance and abrasion resistance by the above-mentioned method. The results obtained are shown in Table 3.
- Example 18 ⁇ Preparation of coating composition consisting of polyarylate having a conjugated diene group and polycarbonate having a dienophil group, and preparation of a crosslinked resin film> 1.2 g of PAR-1 and 0.3 g of PC-2 were weighed in a sample tube with a screw cap and dissolved in 10 mL of tetrahydrofuran to obtain a coating composition.
- the obtained coating liquid composition was cast into a 250 ⁇ m-thick PET film using an applicator with a gap of 200 ⁇ m. After air-drying for 1 hour, the mixture was treated with a vacuum dryer at a temperature of 50 ° C. for 16 hours to remove the solvent to obtain a precursor film.
- the obtained precursor film was heated in a vacuum drier (decompression degree is 1 to 100 Pa) at a temperature of 200 ° C. for 1 hour for cross-linking treatment to obtain a resin film.
- Example 19 ⁇ Preparation of a coating composition for a charge transport layer composed of polyarylate having a conjugated diene group, polycarbonate having a dienophil group, and a charge transport substance, and preparation of a crosslinked resin film>
- a coating composition for a charge transport layer composed of polyarylate having a conjugated diene group, polycarbonate having a dienophil group, and a charge transport substance, and preparation of a crosslinked resin film.
- CTM-1 charge transporter
- a liquid composition was obtained.
- the obtained coating liquid composition was cast into a 250 ⁇ m-thick PET film using an applicator with a gap of 200 ⁇ m.
- the mixture was treated with a vacuum dryer at a temperature of 50 ° C. for 16 hours to remove the solvent to obtain a precursor film.
- the obtained precursor film was heated in a vacuum drier (decompression degree of 1 to 100 Pa) at a temperature of 150 ° C. for 1 hour for cross-linking treatment to obtain a resin film.
- Example 19 A coating composition and a resin film were obtained in the same manner as in Example 2 except that PC-2 was not used in Example 19 and the amount of PAR-1 used was changed to 1.5 g.
- Example 3 The film obtained in Example 3 after drying (after drying at 50 ° C. for 16 hours) for the purpose of removing the solvent, the film after heat-treating the film at 200 ° C. for 3 hours, and the film of Comparative Example 3-1 were used.
- the film was peeled off, and a three-dimensional spectrum measurement of excited fluorescence was performed. The obtained results are shown in FIG.
- the spectrum shown in FIG. 3 is the result of cutting out the measured three-dimensional fluorescence spectrum at an excitation wavelength of 350 nm and a fluorescence wavelength of 400 to 600 nm.
- the resin film shown in Comparative Example 3-1 shows fluorescence peculiar to the anthracene skeleton, but in the film mixed with the PC having a maleimide group of Example 1, the drying conditions for removing the solvent (50 ° C., 16 hours). However, the fluorescence emission intensity was significantly reduced. Further heat treatment at 200 ° C. for 3 hours eliminated the fluorescence. From this, it was confirmed that the anthracene skeleton was converted into a non-fluorescent skeleton by the reaction.
- the film obtained in Example 3 after heat treatment at 200 ° C. for 3 hours was peeled off, the carbonate bond was hydrolyzed under alkaline conditions, and the fragmented components were analyzed by LC-MS.
- This compound contains the 9- (4-hydroxybenzyl) -10- (4-hydroxyphenyl) anthracene component in the PC polymer (PC-5) and 2,2-bis [4- (4) used as a cross-linking agent.
- -Maleimidephenoxy) Phenyl] Propane is considered to be a component produced by binding with Diels-Alder reaction and further hydrolyzing the carbonate group with an alkali. From the above and the general reaction form related to the Diels-Alder reaction, it was confirmed that when the crosslinked precursor composition was heated, a resin having the following crosslinked structure was produced.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Abstract
Description
この有機電子写真感光体には、適用される電子写真プロセスに応じて、所定の感度や電気特性、光学特性を備えていることが要求される。電子写真感光体は、その感光層の表面に、コロナ帯電、トナー現像、紙への転写、およびクリーニング処理などの操作が繰返し行われるため、これら操作を行う度に電気的または機械的な外力が加えられる。したがって、長期間にわたって電子写真の画質を維持するためには、電子写真感光体の表面に設けた感光層に、これら外力に対する耐久性が要求される。また、有機電子写真感光体は、通常機能性材料と共にバインダー樹脂を有機溶剤に溶解し、導電性基板などにキャスト製膜する方法で製造されることから、有機溶剤への溶解性・安定性が求められる。
特許文献5には、アリル基を持つポリカーボネートに特定構造のトリアリールアミン、およびトリアリールアミン構造を持たないラジカル重合性化合物を用いて、無触媒で加熱により架橋する方法が開示されている。
また、特許文献7には、フラン構造を持つ脂肪族ポリエステル、ポリアミド、またはポリウレアと多官能マレイミドとの反応による架橋樹脂が開示されている。
特許文献8には、アントラセン骨格にアクリル基などの重合性官能基を導入し、当該官能基の部分で架橋反応を行う硬化性組成物が開示されている。
非特許文献1には、脂肪族-芳香族ポリエステルの一部にアントラセンジカルボン酸骨格を導入した樹脂を2官能のマレイミド化合物で架橋した樹脂が開示されている。
このような例として、特許文献5には、ラジカル重合活性が高く、開始剤の使用やUVの照射なく加熱するだけでラジカル重合するモノマーを使用し、そこにアリル基を持つポリカーボネートを共存させる技術が報告されている。しかしながら、開始剤や光照射がなくてもラジカル重合するモノマーを使用していることから当該重合性モノマー単独の重合物が主に生成し、相対的にラジカル重合活性が低いアリル基を持つポリカーボネートと当該重合性モノマーの反応確率は低いと考えられる。そのため、得られた組成物はポリマーの緻密な3次元網目構造を持つのではなく、ポリカーボネート樹脂とラジカル重合モノマーの架橋重合物が別々に存在し、その一部分のみが結合された組成物になっていると考えられる。そして、通常低分子として存在する電荷輸送物質が高分子量化することによる物性向上の効果が支配的で、ポリカーボネート部分が架橋されることによる物性向上は不十分なものであった。また、開始剤がなくてもラジカル重合が進行する高活性な化合物を使用しているため、塗液組成物の段階で重合が進行することを抑制するのが困難であり、塗液保管中の粘度の上昇や、ゲル化などの問題があった。
非特許文献1には、ポリエチレンテレフタレート(PET)にアントラセンジカルボン酸骨格を導入し、2官能のマレイミド化合物により架橋する例が記載されている。この例の目的は、加熱架橋により機械物性を向上させる点では本発明の目的と類似するが、非特許文献1には、ポリカーボネートやポリアリレートに適用する例は記載も示唆も無い。また、PETは、電子写真感光体用途に使用することを考えると通常塗布溶剤として使用されるTHFなどの有機溶剤への溶解性が低く、またトリアリールアミンなどの電荷輸送物質との相溶性が悪く、当該用途には使用することができない。
本実施形態に係る樹脂は、芳香族ポリカーボネートおよびポリアリレートからなる群から選択される少なくとも1つの樹脂である。具体的な樹脂としては、芳香族ポリカーボネート、ポリアリレート、および芳香族ポリカーボネート-ポリアリレート共重合体(以下、これらを単に「PC類」ともいう)が挙げられる。
本実施形態に係る樹脂は、ディールス・アルダー反応による高分子鎖間の結合を有する。また、高分子鎖間の結合を有する樹脂は、下記一般式(S1)で表される構造を有する。下記一般式(S1)において、*は、結合位置を表す。また、波線より先の部分の構造は、特に限定されないが、波線より先の部分のいずれかには、少なくとも1つの結合位置を有する。なお、波線より先の部分は、連結された環状構造(芳香族環、および複素環を含む)を形成してもよい。また、芳香族環、および複素環は、3員環、4員環、5員環、6員環、および7員環などのいずれであってもよい。そして、高分子鎖間を結合する架橋部位の構造は、例えば、下記一般式で示すような結合様式となる。
このように、本実施形態に係る架橋様式は、リジッドな環状構造を持つ点が、直鎖状の構造となる一般的なラジカル反応による架橋との相違点である。環状構造を持つことで、直鎖状の架橋と比較するとより強固な構造となり、機械強度が同等の架橋密度の直鎖状の架橋様式の樹脂より向上することの一因になっていると考えられる。
なお、本発明者らは、前記した本発明の課題を解決するために鋭意研究を重ねた結果、ディールス・アルダー反応により架橋するPC類が溶液安定性に優れ、現状の感光体製造プロセス温度で架橋し、得られた架橋樹脂の耐摩耗性が優れ、電気特性の悪化が見られないことを見出した。本発明は、このような知見に基づいて完成されたものである。
本実施形態に係る高分子鎖間の結合は、例えば、以下のような組合せの反応により形成できる。
(i)高分子鎖に2つ以上の共役ジエン構造を持つ高分子と、2官能以上のジエノフィル基を持つ化合物との反応
(ii)高分子鎖に2つ以上のジエノフィル構造を持つ高分子と、2官能以上の共役ジエン基を持つ化合物との反応
(iii)高分子鎖に2つ以上の共役ジエン構造を持つ高分子と、高分子鎖に2つ以上のジエノフィル構造を持つ高分子との反応
(iv)一本の高分子鎖に共役ジエン構造およびジエノフィル構造の双方の構造を持ち、高分子鎖一本当たりの前記共役ジエン構造および前記ジエノフィル構造の平均個数がそれぞれ1以上である高分子の反応
(i-1)
高分子鎖の主鎖に2つ以上の共役ジエン構造を有する高分子と、2官能以上のジエノフィル基を有する化合物との反応
2つのジエノフィル構造を有する高分子であって、高分子鎖の両末端に当該ジエノフィル構造を1つずつ有する高分子と、
高分子鎖に2つを超える共役ジエン構造を有する高分子と、の反応
2つのジエノフィル構造を有する高分子であって、高分子鎖の両末端に当該ジエノフィル構造を1つずつ有する高分子と、
高分子鎖に2つを超える共役ジエン構造を有する高分子であって、当該高分子鎖の両末端に当該共役ジエン構造を1つずつ有し、かつ主鎖内にも当該共役ジエン構造を1以上有する高分子と、の反応
2つのジエノフィル構造を有する高分子であって、高分子鎖の両末端に当該ジエノフィル構造を1つずつ有する高分子と、
高分子鎖に2つを超える共役ジエン構造を有する高分子であって、当該高分子鎖の一方の末端に当該共役ジエン構造を1つ有し、他方の末端には当該共役ジエン構造を有さず、かつ主鎖内に当該共役ジエン構造を2つ以上有する高分子と、の反応
2つのジエノフィル構造を有する高分子であって、高分子鎖の両末端に当該ジエノフィル構造を1つずつ有する高分子と、
高分子鎖の両末端には共役ジエン構造を有さず、かつ主鎖内に2つを超える共役ジエン構造を有する高分子と、の反応
2つの共役ジエン構造を有する高分子であって、高分子鎖の両末端に当該共役ジエン構造を1つずつ有する高分子と、
高分子鎖に2つを超えるジエノフィル構造を有する高分子との反応
2つの共役ジエン構造を有する高分子であって、高分子鎖の両末端に当該共役ジエン構造を1つずつ有する高分子と、
高分子鎖に2つを超えるジエノフィル構造を有する高分子であって、当該高分子鎖の両末端にジエノフィル構造を1つずつ有し、かつ主鎖内にもジエノフィル構造を1つ以上有する高分子と、の反応
2つの共役ジエン構造を有する高分子であって、高分子鎖の両末端に当該共役ジエン構造を1つずつ有する高分子と、
高分子鎖に2つを超えるジエノフィル構造を有する高分子であって、当該高分子鎖の一方の末端にジエノフィル構造を1つ有し、他方の末端にはジエノフィル構造を有さず、かつ主鎖内にジエノフィル構造を2つ以上有する高分子と、の反応
2つの共役ジエン構造を有する高分子であって、高分子鎖の両末端に当該共役ジエン構造を1つずつ有する高分子と、
高分子鎖の両末端にはジエノフィル構造を有さず、かつ主鎖内に2つを超えるジエノフィル構造を有する高分子と、の反応
また、例えば、前記(iii)の反応の場合、2つ以上の共役ジエン構造を有する高分子において、高分子鎖の主鎖に全ての共役ジエン構造が結合し、かつ、2つ以上のジエノフィル構造を有する高分子において、高分子鎖の主鎖に全てのジエノフィル構造が結合していてもよい。
(iv-1)高分子鎖の一方の末端および他方の末端の少なくともいずれかの末端には、共役ジエン構造およびジエノフィル構造が結合していない高分子
(iv-2)高分子鎖の一方の末端には、共役ジエン構造およびジエノフィル構造の一方が結合し、高分子鎖の他方の末端には、共役ジエン構造およびジエノフィル構造のいずれも結合せず、高分子鎖の主鎖に共役ジエン構造およびジエノフィル構造の他方が少なくとも1つ結合する高分子
(iv-3)高分子鎖の末端には共役ジエン構造およびジエノフィル構造が結合していない高分子
(iv-4)高分子鎖の両末端にジエノフィル構造が1つずつ結合し、かつ高分子鎖の主鎖に共役ジエン構造が少なくとも1つ結合する高分子
すなわち、本実施形態に係る樹脂における高分子鎖間の結合は、一方の高分子の末端に結合している共役ジエン構造およびジエノフィル構造の一方と、他方の高分子の主鎖に結合している共役ジエン構造およびジエノフィル構造の他方との結合であるか、および一方の高分子の主鎖に結合している共役ジエン構造およびジエノフィル構造の一方と、他方の高分子の主鎖に結合している共役ジエン構造およびジエノフィル構造の他方との結合の少なくともいずれかを持つことも好ましい。
また、高分子鎖の末端同士の結合でなくても、反応性基を2つ持つ高分子鎖同士の結合の場合も、同様に3次元架橋は起こらず、直鎖状の高分子になる。そのため、本実施形態に係る樹脂における高分子鎖間の結合は、高分子鎖に2つの反応点(反応性基)を持つ高分子同士(例えば、末端に反応性基を持つ高分子同士)のみの反応による結合ではないことも好ましい。
共役ジエン構造としては、ジヒドロキシアントラセン、アントラセンジカルボン酸、9-(4-ヒドロキシベンジル)-10-(4-ヒドロキシフェニル)アントラセン、9-(3-メチル-4-ヒドロキシベンジル)-10-(3-メチル-4-ヒドロキシフェニル)アントラセン、9-(4-ヒドロキシフェニル)アントラセン、9-(3-メチル-4-ヒドロキシフェニル)アントラセン、9,10-ビス(4-ヒドロキシフェニル)アントラセン、9,10-ビス(3-メチル-4-ヒドロキシフェニル)アントラセン、ヒドロキシアントラセン、1,4-ジヒドロキシアントラセン、アントラセンカルボン酸、2-(2-フラニルメチル)ヒドロキノン、フランジカルボン酸、およびイソオイゲノールなどから誘導される基が挙げられる。
R1は、各々独立に、
単結合、
他の骨格との結合基、
水素原子、
炭素数1以上、12以下の脂肪族炭化水素基、
環形成炭素数6以上、12以下の芳香族炭化水素基、または
炭素数1以上、10以下のアルコキシ基であり、
R1のうち1つ、または2つは、単結合、または他の骨格との連結基であり、
当該連結基としてのR1は、炭素原子、酸素原子、窒素原子、硫黄原子、ケイ素原子、リン原子およびホウ素原子からなる群から選択される少なくともいずれかの原子を含み、連結基を構成する原子同士の結合様式が全て共有結合からなる基である。
また、複数のR1が連結された環状構造(芳香族環、および複素環を含む)を形成してもよい。
炭素数1以上、12以下の脂肪族炭化水素基としてのアルキル基は、例えば、メチル基、エチル基、n-プロピル基、n-ブチル基、n-ペンチル基、n-ヘキシル基、イソプロピル基、イソブチル基、sec-ブチル基、tert-ブチル基、イソペンチル基、ネオペンチル基、tert-ペンチル基、イソヘキシル基、sec-ヘキシル基、tert-ヘキシル基、ヘプチル基、オクチル基、ノニル基、デシル基、ウンデシル基、およびドデシル基などが挙げられる。
炭素数1以上、12以下の脂肪族炭化水素基としてのアルケニル基は、例えば、ビニル基(エテニル基、1-プロペニル基、2-プロペニル基、2-ブテニル基、1-ブテニル基、1-ヘキセニル基、オクテニル基、デセニル基、およびドデセニル基などが挙げられる。
炭素数1以上、12以下の脂肪族炭化水素基としてのアルキニル基は、例えば、エチニル基、1-プロピニル基、2-プロピニル基、1-ブチニル基、3-ヘキシニル基、オクチニル基、デシニル基、およびドデシニル基などが挙げられる。
X1は、各々独立に、
-O-、
-(C=O)-O-、
-O-(C=O)-O-、
-O-(C=O)-、または
-S-であり、
R11は、各々独立に、
水素原子、
炭素数1以上、12以下の脂肪族炭化水素基、
環形成炭素数6以上、12以下の芳香族炭化水素基、または
炭素数1以上、10以下のアルコキシ基であり、
また、複数のR11が連結された環状構造(芳香族環、および複素環を含む)を形成してもよい。
R12は、各々独立に、
水素原子、
炭素数1以上、12以下の脂肪族炭化水素基、または
炭素数6以上、12以下の芳香族炭化水素基であり、
nは、0、または置換可能な数を上限とした自然数を表す。
*は、結合位置を示す。
R13は、各々独立に、
水素原子、
炭素数1以上、12以下の脂肪族炭化水素基、または
炭素数6以上、12以下の芳香族炭化水素基である。
なお、前記一般式(DE14)において、
R13は、各々独立に、
炭素数1以上、12以下の脂肪族炭化水素基、または
炭素数6以上、12以下の芳香族炭化水素基であることが好ましい。
*は、結合位置を示す。
R11は、各々独立に、
水素原子、
ハロゲン原子、
炭素数1以上、12以下の脂肪族炭化水素基、
環形成炭素数6以上、12以下の芳香族炭化水素基、または
炭素数1以上、10以下のアルコキシ基であり、
また、複数のR11が連結された環状構造(芳香族環、および複素環を含む)を形成してもよい。
前記一般式(DE17)において、
mは、0以上、8以下の整数を表す。
前記一般式(DE18)において、
nは、0以上、4以下の整数を表し、
mは、0以上、9以下の整数を表す。
*は、結合位置を示す。
R11は、各々独立に、
水素原子、
ハロゲン原子、
炭素数1以上、12以下の脂肪族炭化水素基、
環形成炭素数6以上、12以下の芳香族炭化水素基、または
炭素数1以上、10以下のアルコキシ基であり、
また、複数のR11が連結された環状構造(芳香族環、および複素環を含む)を形成してもよい。
nは、0以上、3以下の整数を表す。
*は、結合位置を示す。
ジエノフィル構造としては、4,4’-ジフェニルメタンビスマレイミド、m-フェニレンビスマレイミド、2,2-ビス[4-(4-マレイミドフェノキシ)フェニル]プロパン、ビスフェノールAジフェニルエーテルビスマレイミド、3,3’-ジメチル-5,5’-ジエチル-4,4’-ジフェニルメタンビスマレイミド、4-メチル-1,3-フェニレンビスマレイミド、1,6-ビスマレイミド-(2,2,4-トリメチル)ヘキサン、4,4’-ジフェニルエーテルビスマレイミド、4,4’-ジフェニルスルフォンビスマレイミド、1,3-ビス(3-マレイミドフェノキシ)ベンゼン、1,3-ビス(4-マレイミドフェノキシ)ベンゼン、4,4’-メチレンジアニリンを有するジフェニルメタン-4,4’-ビスマレイミドポリマー、N,N’-(2,2’-ジエチル-6,6’-ジメチレンジフェニレン)ビスマレイミド、N,N’-(4-メチル-m-フェニレン)ビスマレイミド、N,N’-m-フェニレンジマレイミド、N,N’-m-フェニレンビスマレイミド、ポリフェニルメタンビスマレイミドなどのビスマレイミド類、N-フェニルマレイミドなどのモノマレイミド類、および下記化合物で分子末端が停止された構造を持つPC類が挙げられる。
X2は、単結合、または他の骨格との連結基であり、
当該連結基としてのX2は、炭素原子、酸素原子、窒素原子、硫黄原子、ケイ素原子、リン原子およびホウ素原子からなる群から選択される少なくともいずれかの原子を含み、連結基を構成する原子同士の結合様式が全て共有結合からなる基である。
*は、結合位置を示す。
前記一般式(DP3)におけるY2は、芳香族ポリカーボネート骨格またはポリアリレート骨格を含む基である。
*は、結合位置を示す。
m3は、0、1または2であり、
n3は、4であり、
複数のR3は、各々独立に
水素原子、
ハロゲン原子、
炭素数1以上、10以下のアルキル、
環形成炭素数6以上、12以下のアリール、または
炭素数1以上、10以下のフッ化アルキルであり、
X3は、各々独立に、
単結合、
-C(-R31)2-、
-O-、
-S-、
-SO-、
-SO2-、
-N(-R32)-,
-P(-R33)-、
-P=O(-R34)-、
カルボニル、
エステル、
アミド、
炭素数2以上、20以下のアルキレン、
炭素数2以上、20以下のアルキリデン、
環形成炭素数3以上、20以下のシクロアルキレン、
環形成炭素数3以上、20以下のシクロアルキリデン、
環形成炭素数6以上、20以下のアリーレン、
環形成炭素数4以上、20以下のビシクロアルカンジイル、
環形成炭素数5以上、20以下のトリシクロアルカンジイル、
環形成炭素数4以上、20以下のビシクロアルキリデン、および
環形成炭素数5以上、20以下のトリシクロアルキリデンからなる群から選択される1種または2種以上からなる基であり、
R31からR34は、各々独立に、
水素原子、
ハロゲン原子、
炭素数1以上、10以下のアルキル、
環形成炭素数6以上、12以下のアリール、または
炭素数1以上、10以下のフッ化アルキルである。
*は、結合位置を示す。
前記一般式(UN11)中、X3が示す炭素数2以上、20以下のアルキリデンは、エチリデン、プロピリデン、ブチリデン、ヘキシリデン、オクチリデン、デシリデン、ペンタデシリデン、イコシリデンなどの基が挙げられる。
前記一般式(UN11)中、X3が示す炭素数3以上、20以下のシクロアルキレンは、直鎖状または分岐状のアルキレン基が挙げられ、例えば、シクロプロピレン、シクロブチレン、シクロへキシレン、シクロオクチレン、シクロデシレン、シクロペンタデシレン、およびシクロイコシレンなどの基が挙げられる。
前記一般式(UN11)中、X3が示す炭素数3以上、20以下のシクロアルキリデンは、シクロプロピリデン、シクロブチリデン、シクロヘキシリデン、シクロオクチリデン、シクロデシリデン、シクロドデシリデン、シクロペンタデシリデン、およびシクロイコシリデンなどの基が挙げられる。
前記一般式(UN11)中、X3が示す環形成炭素数6以上、20以下のアリーレンは、例えば、フェニレン、ナフチレン、およびビフェニレンなどの基が挙げられる。
前記一般式(UN11)中、X3が示す環形成炭素数4以上、20以下のビシクロアルキリデンは、上述のシクロアルキリデンの二環体が例示され、環形成炭素数5以上、20以下のトリシクロアルキリデンは、上述のシクロアルキリデンの三環体、例えばアダマンチリデン、トリシクロデシリデンが例示される。
本実施形態に係る樹脂前駆体組成物は、架橋反応により、前述の本実施形態に係る樹脂を作製できるものである。
すなわち、本実施形態に係る樹脂前駆体組成物は、ディールス・アルダー反応性を持つ共役ジエンおよびジエノフィルの少なくとも1種を構造中に有する高分子と、それぞれの相手方の基を持つ架橋剤または高分子とを組合せで含むものである。
(b1)高分子鎖に2つ以上の共役ジエン構造を持つ高分子と、2官能以上のジエノフィル基を持つ化合物
(b2)高分子鎖に2つ以上のジエノフィル構造を持つ高分子と、2官能以上の共役ジエン基を持つ化合物
(b3)高分子鎖に2つ以上の共役ジエン構造を持つ高分子と、高分子鎖に2つ以上のジエノフィル構造を持つ高分子
(b4)一本の高分子鎖に共役ジエン構造およびジエノフィル構造の双方の構造を持ち、高分子鎖一本当たりの前記共役ジエン構造および前記ジエノフィル構造の平均個数がそれぞれ1以上である高分子
高分子鎖の主鎖に2つ以上の共役ジエン構造を有する高分子と、2官能以上のジエノフィル基を有する化合物
2つのジエノフィル構造を有する高分子であって、高分子鎖の両末端に当該ジエノフィル構造を1つずつ有する高分子、および
高分子鎖に2つを超える共役ジエン構造を有する高分子
2つのジエノフィル構造を有する高分子であって、高分子鎖の両末端に当該ジエノフィル構造を1つずつ有する高分子、および
高分子鎖に2つを超える共役ジエン構造を有する高分子であって、当該高分子鎖の両末端に当該共役ジエン構造を1つずつ有し、かつ主鎖内にも当該共役ジエン構造を1以上有する高分子
2つのジエノフィル構造を有する高分子であって、高分子鎖の両末端に当該ジエノフィル構造を1つずつ有する高分子、および
高分子鎖に2つを超える共役ジエン構造を有する高分子であって、当該高分子鎖の一方の末端に当該共役ジエン構造を1つ有し、他方の末端には当該共役ジエン構造を有さず、かつ主鎖内に当該共役ジエン構造を2つ以上有する高分子
2つのジエノフィル構造を有する高分子であって、高分子鎖の両末端に当該ジエノフィル構造を1つずつ有する高分子、および
高分子鎖の両末端には共役ジエン構造を有さず、かつ主鎖内に2つを超える共役ジエン構造を有する高分子
2つの共役ジエン構造を有する高分子であって、高分子鎖の両末端に当該共役ジエン構造を1つずつ有する高分子、および
高分子鎖に2つを超えるジエノフィル構造を有する高分子
2つの共役ジエン構造を有する高分子であって、高分子鎖の両末端に当該共役ジエン構造を1つずつ有する高分子、および
高分子鎖に2つを超えるジエノフィル構造を有する高分子であって、当該高分子鎖の両末端にジエノフィル構造を1つずつ有し、かつ主鎖内にもジエノフィル構造を1つ以上有する高分子
2つの共役ジエン構造を有する高分子であって、高分子鎖の両末端に当該共役ジエン構造を1つずつ有する高分子、および
高分子鎖に2つを超えるジエノフィル構造を有する高分子であって、当該高分子鎖の一方の末端にジエノフィル構造を1つ有し、他方の末端にはジエノフィル構造を有さず、かつ主鎖内にジエノフィル構造を2つ以上有する高分子
2つの共役ジエン構造を有する高分子であって、高分子鎖の両末端に当該共役ジエン構造を1つずつ有する高分子、および
高分子鎖の両末端にはジエノフィル構造を有さず、かつ主鎖内に2つを超えるジエノフィル構造を有する高分子
また、例えば、前記(b3)の成分を含有する組成物の場合、2つ以上の共役ジエン構造を有する高分子において、高分子鎖の主鎖に全ての共役ジエン構造が結合し、かつ、2つ以上のジエノフィル構造を有する高分子において、高分子鎖の主鎖に全てのジエノフィル構造が結合していてもよい。
(b4-1)高分子鎖の一方の末端および他方の末端の少なくともいずれかの末端には、共役ジエン構造およびジエノフィル構造が結合していない高分子
(b4-2)高分子鎖の一方の末端には、共役ジエン構造およびジエノフィル構造の一方が結合し、高分子鎖の他方の末端には、共役ジエン構造およびジエノフィル構造のいずれも結合せず、高分子鎖の主鎖に共役ジエン構造およびジエノフィル構造の他方が少なくとも1つ結合する高分子
(b4-3)高分子鎖の末端には共役ジエン構造およびジエノフィル構造が結合していない高分子
(b4-4)高分子鎖の両末端にジエノフィル構造が1つずつ結合し、かつ高分子鎖の主鎖に共役ジエン構造が少なくとも1つ結合する高分子
すなわち、本実施形態に係る樹脂前駆体組成物を用いた場合に形成される樹脂における高分子鎖間の結合は、一方の高分子の末端に結合している共役ジエン構造およびジエノフィル構造の一方と、他方の高分子の主鎖に結合している共役ジエン構造およびジエノフィル構造の他方との結合であるか、および一方の高分子の主鎖に結合している共役ジエン構造およびジエノフィル構造の一方と、他方の高分子の主鎖に結合している共役ジエン構造およびジエノフィル構造の他方との結合の少なくともいずれかを持つことも好ましい。
また、高分子鎖の末端同士の結合でなくても、反応性基を2つ持つ高分子鎖同士の結合の場合も、同様に3次元架橋は起こらず、直鎖状の高分子になる。そのため、本実施形態に係る樹脂前駆体組成物を用いた場合に形成される樹脂における高分子鎖間の結合は、高分子鎖に2つの反応点(反応性基)を持つ高分子同士(例えば、末端に反応性基を持つ高分子同士)のみの反応による結合ではないことが好ましい。
前記一般式(2)および一般式(2A)において、Ar34は、前記一般式(UN11)で表される基であり、n32は、平均量体数を表す。また、平均量体数n32は、1.0以上、10以下である。
前記一般式(2C)において、Ar33は、前記一般式(DE3)、一般式(DE5)、および一般式(DE8)で表される基からなる群から選択される少なくともいずれかの基であり、Ar34は、前記一般式(UN11)で表される基である。また、n33およびn34は、それぞれ平均量体数を表す。また、平均量体数n33およびn34の合計は、1.0以上、10以下である。
*は、結合位置を示す。
ただし、Ar33およびAr34は、互いに異なる。前記一般式(2C)において、各繰り返し単位は必ずしも連続していなくてもよい。
平均量体数の算出方法は、後述する実施例において説明する方法が挙げられる。
aは、[Ar33]/([Ar33]+[Ar34])であり、bは、[Ar34]/([Ar33]+[Ar34])であり、bが0の場合も含む。[Ar33]は、PC重合体中のAr33で表される基を含む繰り返し単位Aのモル数を表し、[Ar34]は、PC重合体中のAr34で表される基を含む繰り返し単位Bのモル数を表す。
前記一般式(100)で表されるPC重合体は、ブロック共重合体、交互共重合体、およびランダム共重合体など、いずれであってもよい。
本実施形態に係るPC重合体の第二の形態は、前記したPC重合体の連鎖末端として、前記一般式(DE4)、一般式(DE6)、一般式(DE7)、一般式(DE9)、一般式(DE12)、一般式(DE14)一般式(DP1)、一般式(DP3)および、一般式(DP4)で表される構造のいずれかを有するものである。また、上記PC重合体(100)において、Ar33を含まなくてもよいが、その場合、連鎖末端は上記のいずれかの構造を合計で、1分子当たり平均で2つ以上含むことが必要である。ただし、高分子鎖の末端に、共役ジエン構造を2つ以上持たないとき、上記PC重合体(100)は、Ar33を含むことが好ましい。、他方、Ar33を含む骨格の場合には、1分子当たりにAr33に含まれるジエン構造と上記連鎖末端に含まれるジエン構造の数の合計が2以上であればよい。また、1分子当たりにAr33に含まれるジエン構造の数が1つ以上であることが好ましい。
一価の芳香族基は、脂肪族基を含有する基であってもよい。
一価のフッ素含有脂肪族基は、芳香族基を含有する基であってもよい。
また、一価の芳香族基および一価のフッ素含有脂肪族基には、アルキル基、ハロゲン原子、およびアリール基からなる群から選択される少なくともいずれかの置換基が付加していてもよい。これらの置換基には、アルキル基、ハロゲン原子、およびアリール基からなる群から選択される少なくともいずれかの置換基がさらに付加していてもよい。また、置換基が複数ある場合、これらの置換基同士が互いに結合して環を形成してもよい。
芳香族基に付加する置換基、および芳香族基に付加しているアルキル基に付加する置換基としては、フッ素原子、塩素原子、臭素原子などのハロゲン原子が挙げられる。また、芳香族基に付加する置換基として炭素数1から20のアルキル基が挙げられる。このアルキル基は、上記のようにハロゲン原子が付加した基であってもよく、アリール基が付加した基であってもよい。
さらに、一価のフッ素含有脂肪族基としては、エーテル結合を2つ以上有するフッ素含有アルコールから誘導される一価の基でも好ましい。このようなフッ素含有アルコールを用いることで、塗液組成物におけるPC重合体の分散性が良くなり、成形体や電子写真感光体における耐摩耗性を向上させ、摩耗後の、表面潤滑性、撥水性および撥油性を保持することができる。
F(CF2)m1CH2OH・・・(31)
F-(CF2CF2)n 32-(CF2CF2O)n 33-CF2CH2OH・・・(33)
CR3-(CF2)n 35-O-(CF2CF2O)n 34-CF2CH2OH・・・(34)
前記一般式(33)において、n32は0から5の整数であり、好ましくは、0から3の整数である。n33は1から5の整数であり、好ましくは、1から3の整数である。
前記一般式(34)において、n34は1から5の整数であり、好ましくは、1から3の整数である。n35は0から5の整数であり、好ましくは、0から3の整数である。Rは、CF3またはFである。
前記一般式(36)において、Rfは、炭素数が5以上、かつ、フッ素原子数が11以上であるパーフルオロアルキル基、あるいは下記一般式(37)で表されるパーフルオロアルキルオキシ基を示す。
例えば、p-tert-ブチル-フェノール、p-フェニルフェノール、p-クミルフェノール、p-パーフルオロノニルフェノール、p-(パーフルオロノニルフェニル)フェノール、p-(パーフルオロヘキシル)フェノール、p-tert-パーフルオロブチルフェノール、p-パーフルオロオクチルフェノール、1-(p-ヒドロキシベンジル)パーフルオロデカン、p-〔2-(1H,1H-パーフルオロトリドデシルオキシ)-1,1,1,3,3,3-ヘキサフルオロプロピル〕フェノール、3,5-ビス(パーフルオロヘキシルオキシカルボニル)フェノール、p-ヒドロキシ安息香酸パーフルオロドデシル、p-(1H,1H-パーフルオロオクチルオキシ)フェノール、2H,2H,9H-パーフルオロノナン酸などが好適に用いられる。
これら分岐剤の添加割合は、繰り返し単位A、繰り返し単位B、および連鎖末端の共重合組成のモル百分率で、または繰り返し単位A、および連鎖末端の共重合組成のモル百分率で30モル%以下であることが好ましく、5モル%以下であることがより好ましい。分岐剤の添加割合が30モル%以下であると、成形性の低下を抑制できる。
ここで、「実質的に水と混じりあわない」有機溶剤とは、常温常圧条件で、水と有機溶剤を1:9~9:1の組成範囲で混合した場合に、均一な層からなる溶液(ゲル化物および不溶物のいずれもみられない溶液)が得られない有機溶剤である。
また、有機溶剤が「最終的に得られるポリカーボネート共重合体を5質量%以上溶解可能」とは、温度20~30℃、常圧の条件で測定した際のポリカーボネート共重合体の溶解度である。
また、「最終的に得られるポリカーボネート重合体」とは、本実施形態のポリカーボネート重合体の製造方法における重合工程を経て得られる重合体のことで、架橋前のものである。
このような有機溶剤としては、例えば、トルエンなどの芳香族炭化水素類、シクロヘキサノンなどのケトン類、および塩化メチレンなどのハロゲン化炭化水素などが挙げられる。中でも、溶解性が高いことから、塩化メチレンが好ましい。
さらに、必要に応じて、本実施形態のPC重合体の反応系に亜硫酸ナトリウムやハイドロサルファイト塩などの酸化防止剤を少量添加してもよい。
本実施形態に係る塗液組成物は、本実施形態に係る樹脂前駆体組成物と、有機溶剤とを含む。
本実施形態に係る有機溶剤としては、環状エーテル類(テトラヒドロフラン(THF)、ジオキサン、およびジオキソランなど)、環状ケトン類(シクロヘキサノン、シクロペンタノン、およびシクロヘプタノンなど)、芳香族炭化水素類(トルエン、キシレン、およびクロロベンゼンなど)、ケトン類(メチルエチルケトン(MEK)、およびメチルイソブチルケトン(MIBK)など)、ハロゲン化炭化水素類(ジクロロメタン、およびクロロホルムなど)、エステル類(酢酸エチル、酢酸イソプロピル、酢酸イソブチル、および酢酸ブチルなど)、エーテル類(エチレングリコールジメチルエーテル、およびエチレングリコールモノエチルエーテルなど)、アミド類(フマル酸ジメチル(DMF)、およびジメチルアセトアミド(DMAc)など)、および非プロトン性極性溶媒(ジメチルスルホキシド(DMSO)など)などが挙げられる。
これら添加剤や他の樹脂としては、樹脂前駆体組成物と配合し得る物質として公知の物質を用いることができる。
本実施形態に係る塗液組成物中、本実施形態に係る樹脂前駆体組成物は1種単独で用いてもよいし、2種以上を併用してもよい。
また、感光体の保護層の形成に使用することも可能である。
本実施形態に係る成形物は、本実施形態に係る樹脂を含む。本実施形態に係る成形物は、後述する電子写真感光体の用途の他に、様々な用途に使用できる。例えば、電子デバイスなどの基板、絶縁層、保護層、接着層、導電層、および構造材などの用途に好適に用いることができる。
本実施形態に係る樹脂前駆体組成物を用いる場合、その成形方法としては、湿式成形法、および溶融成形法のいずれの方法も適用できる。
なお、湿式成形法においては、前述の本実施形態に係る塗液組成物を用いることができる。
本実施形態に係る電子写真感光体は、本実施形態に係る樹脂を最外層に含むことが好ましい。
本実施形態に係る電子写真感光体は、基板と、この基板上に設けられた感光層とを有し、この感光層に、本実施形態に係る樹脂を含む。
本実施形態の電子写真感光体は、本実施形態に係る樹脂を感光層中に用いる限り、公知の種々の形式の電子写真感光体はもとより、どのような電子写真感光体としてもよいが、感光層が、少なくとも1層の電荷発生層と少なくとも1層の電荷輸送層とを有する積層型電子写真感光体、または、一層に電荷発生物質と電荷輸送物質とを有する単層型電子写真感光体とすることが好ましい。
本実施形態の電子写真感光体において、本実施形態に係る樹脂は、1種単独で使用してもよいし、2種以上を組合せて用いてもよい。また、所望に応じて本実施形態の目的を阻害しない範囲で、他のポリカーボネートなどのバインダー樹脂成分を含有させてもよい。さらに、酸化防止剤などの添加物を含有させてもよい。
さらに、各層間の接着性を向上させるための接着層あるいは電荷のブロッキングの役目を果すブロッキング層などの中間層などが形成されていてもよい。
前記した電荷発生層や電荷輸送層のバインダー樹脂としては、特に制限はなく、公知の各種の樹脂を使用することができる。具体的には、例えば、ポリスチレン、ポリ塩化ビニル、ポリ酢酸ビニル、塩化ビニル-酢酸ビニル共重合体、ポリビニルアセタール、アルキッド樹脂、アクリル樹脂、ポリアクリロニトリル、ポリカーボネート、ポリウレタン、エポキシ樹脂、フェノール樹脂、ポリアミド、ポリケトン、ポリアクリルアミド、ブチラール樹脂、ポリエステル樹脂、塩化ビニリデン-塩化ビニル共重合体、メタクリル樹脂、スチレン-ブタジエン共重合体、塩化ビニリデン-アクリロニトリル共重合体、塩化ビニル-酢酸ビニル-無水マレイン酸共重合体、シリコン樹脂、シリコンアルキッド樹脂、フェノール-ホルムアルデヒド樹脂、スチレン-アルキッド樹脂、メラミン樹脂、ポリエーテル樹脂、ベンゾグアナミン樹脂、エポキシアクリレート樹脂、ウレタンアクリレート樹脂、ポリ-N-ビニルカルバゾール、ポリビニルブチラール、ポリビニルホルマール、ポリスルホン、カゼイン、ゼラチン、ポリビニルアルコール、エチルセルロース、ニトロセルロース、カルボキシ-メチルセルロース、塩化ビニリデン系ポリマーラテックス、アクリロニトリル-ブタジエン共重合体、ビニルトルエン-スチレン共重合体、大豆油変性アルキッド樹脂、ニトロ化ポリスチレン、ポリメチルスチレン、ポリイソプレン、ポリチオカーボネート、ポリアリレート、ポリハロアリレート、ポリアリルエーテル、ポリビニルアクリレート、およびポリエステルアクリレートなどが挙げられる。
これらは、1種を単独で用いることもできるし、また、2種以上を混合して用いることもできる。なお、電荷発生層および/または電荷輸送層におけるバインダー樹脂としては、前記した本実施形態のPC重合体を使用することが好適である。
この電荷輸送層において、本実施形態のPC重合体は1種単独で用いることもでき、また2種以上混合して用いることもできる。また、本発明の目的を阻害しない範囲で、他のバインダー樹脂を本実施形態のPC重合体と併用することも可能である。
本実施形態のPC重合体と共に使用できる電荷輸送物質としては、公知の各種の化合物を使用することができる。このような化合物としては、例えば、カルバゾール化合物、インドール化合物、イミダゾール化合物、オキサゾール化合物、ピラゾール化合物、オキサジアゾール化合物、ピラゾリン化合物、チアジアゾール化合物、アニリン化合物、ヒドラゾン化合物、芳香族アミン化合物、脂肪族アミン化合物、スチルベン化合物、フルオレノン化合物、ブタジエン化合物、キノン化合物、キノジメタン化合物、チアゾール化合物、トリアゾール化合物、イミダゾロン化合物、イミダゾリジン化合物、ビスイミダゾリジン化合物、オキサゾロン化合物、ベンゾチアゾール化合物、ベンズイミダゾール化合物、キナゾリン化合物、ベンゾフラン化合物、アクリジン化合物、フェナジン化合物、ポリ-N-ビニルカルバゾール、ポリビニルピレン、ポリビニルアントラセン、ポリビニルアクリジン、ポリ-9-ビニルフェニルアントラセン、ピレン-ホルムアルデヒド樹脂、エチルカルバゾール樹脂、あるいはこれらの構造を主鎖や側鎖に有する重合体などが好適に用いられる。これら化合物は、1種を単独で使用してもよいし、2種以上を組み合わせて使用してもよい。
これら電荷輸送物質の中でも、特開平11-172003号公報において具体的に例示されている化合物、および以下の構造で表される電荷輸送物質が特に好適に用いられる。
また、前記導電性基体と感光層との間には、通常使用されるような公知のブロッキング層を設けることができる。このブロッキング層としては、前記のバインダー樹脂と同種の樹脂を用いることができる。また本実施形態に係る樹脂前駆体組成物を用いてもよい。このブロッキング層の厚みは、0.01μm以上20μm以下、好ましくは0.1μm以上10μm以下である。この厚みが0.01μm以上であると、ブロッキング層を均一に形成することが可能となり、また20μm以下であると電子写真特性が低下することを抑制できる。
このような酸化防止剤の具体例としては、特開平11-172003号公報の明細書に記載された化学一般式[化94]から[化101]の化合物が好適である。
これら酸化防止剤は、1種単独で用いてもよく、2種以上を混合して用いてもよい、そして、これらは前記感光層のほか、表面保護層や下引き層、ブロッキング層に添加してもよい。
各層の塗布は公知の装置など各種の塗布装置を用いて行うことができ、具体的には、例えば、アプリケーター、スプレーコーター、バーコーター、チップコーター、ロールコーター、ディップコーター、およびドクターブレードなどを用いて行うことができる。
本実施形態に係る電子写真感光体の製造方法は、本実施形態に係る塗液組成物を湿式成形法で導電性基体に塗布する工程と、加熱を行うことにより、この塗液組成物中の有機溶剤を除去する工程と、この有機溶剤を除去する工程における加熱と同時、または引き続き加熱を行うことにより、この塗液組成物中の樹脂前駆体組成物の架橋反応を行う工程と、を備える方法である。
有機溶剤を除去する工程において、本実施形態に係る塗液組成物における有機溶剤の種類に応じて、適宜設定できる。
樹脂前駆体組成物の架橋反応を行う工程において、加熱温度は、本実施形態に係る成形物における電子写真感光体向けの架橋温度と同様である。
<製造例1:ビスフェノールZオリゴマー(ビスクロロホーメート)の合成>
1,1-ビス(4-ヒドロキシフェニル)シクロヘキサン(ビスフェノールZ)60.0g(224ミリモル)を塩化メチレン1080mLで懸濁し、そこにホスゲン66.0g(667ミリモル)を加えて溶解させた。これにトリエチルアミン44.0g(435ミリモル)を塩化メチレン120mLに溶解させた液を、温度5℃から15℃の範囲で滴下した。次に、30分間撹拌後、塩化メチレンを所定濃度になるまで留去した。残液に、純水210mL、濃塩酸1.2g、ハイドロサルファイト450mgを加え洗浄した。その後、純水210mLで5回洗浄を繰り返し、分子末端にクロロホーメート基を有するビスフェノールZオリゴマーの塩化メチレン溶液を得た。得られた溶液のクロロホーメート濃度は1.12モル/L、固形物濃度は0.225kg/L、平均量体数は1.03であった。以後この得られた原料をZ-CFという。
平均量体数(nX)=1+(Mav-M1)/M2・・・(数1)
(前記数式(数1)において、Mavは(2×1000/(CF価))であり、M2は(M1-98.92)であり、M1は、下記一般式(X1)において、nX=1のときのビスクロロホーメート化合物の分子量であり、CF価(N/kg)は(CF値/濃度)であり、CF値(N)は反応溶液1Lに含まれる下記一般式(X1)で表されるビスクロロホーメート化合物中のクロル原子数であり、濃度(kg/L)は反応溶液1Lを濃縮して得られる固形分の量である。ここで、98.92は、ビスクロロホーメート化合物同士の重縮合で脱離する2個の塩素原子、1個の酸素原子および1個の炭素原子の合計の原子量である。)
なお、2種類以上の原料を用いてビスクロロホーメートを合成した場合の平均量体数を求める際には、用いた原料の分子量をモル比で平均した分子量に基づきM1を算出して求める。例として、分子量268のモノマーを366モル、分子量214のモノマーを108モル使用して合成した場合、M1は、 次の計算式で算出される。
M1=(268×(366÷(366+108))+214×(108÷(366+108))+124.9
このM1の計算式における「124.9」は、使用するモノマーの水素原子2つが無くなり、炭素原子、酸素原子、および塩素原子がそれぞれ2つ増加した際の分子量増分である。
前記一般式(2A)で表されるビスクロロホーメートオリゴマーの場合は、Ar34が、ArX1に相当し、n32が、nXに相当する。
1,1-ビス(4-ヒドロキシフェニル)シクロヘキサン(ビスフェノールZ)98g(366ミリモル)、3,3’-ジメチル-4,4’-ジヒドロキシビフェニル22g(103ミリモル)を塩化メチレン2400mLで懸濁し、そこにホスゲン138g(1395ミリモル)を加えて溶解させた。これにトリエチルアミン93.8g(929ミリモル)を塩化メチレン256mLに溶解させた液を、温度16℃から19℃の範囲で滴下した。次に、140分間撹拌後、塩化メチレンを所定濃度になるまで留去した。残液に、純水1100mL、濃塩酸2.4g、ハイドロサルファイト450mgを加え洗浄した。その後、純水210mLで5回洗浄を繰り返し、分子末端にクロロホーメート基を有するビスフェノールZオリゴマー、および3,3’-ジメチル-4,4’-ジヒドロキシビフェニルオリゴマーの塩化メチレン溶液を得た。得られた溶液のクロロホーメート濃度は0.57モル/L、固形物濃度は0.11kg/L、平均量体数は1.02であった。以後この得られた原料をZOCBP-CFという。
3,3’-ジメチル-4,4’-ジヒドロキシビフェニル100.4g(469ミリモル)を塩化メチレン2400mLで懸濁し、そこにホスゲン138g(1395ミリモル)を加えて溶解させた。これにトリエチルアミン93.8g(929ミリモル)を塩化メチレン256mLに溶解させた液を、温度16℃から19℃の範囲で滴下した。次に、140分間撹拌後、塩化メチレンを所定濃度になるまで留去した。残液に、純水1100mL、濃塩酸2.4g、ハイドロサルファイト450mgを加え洗浄した。その後、純水210mLで5回洗浄を繰り返し、分子末端にクロロホーメート基を有するビスフェノールZオリゴマー、および3,3’-ジメチル-4,4’-ジヒドロキシビフェニルオリゴマーの塩化メチレン溶液を得た。得られた溶液のクロロホーメート濃度は0.52モル/L、固形物濃度は0.089kg/L、平均量体数は1.01であった。以後この得られた原料をOCBP-CFという。
2,2-ビス(4-ヒドロキシフェニル)ブタン(ビスフェノールB)57g(235ミリモル)、4,4’-ジヒドロキシジフェニルエーテル47g(233ミリモル)を塩化メチレン2400mLで懸濁し、そこにホスゲン138g(1395ミリモル)を加えて溶解させた。これにトリエチルアミン93.8g(929ミリモル)を塩化メチレン256mLに溶解させた液を、温度16℃から19℃の範囲で滴下した。次に、140分間撹拌後、塩化メチレンを所定濃度になるまで留去した。残液に、純水1100mL、濃塩酸2.4g、ハイドロサルファイト450mgを加え洗浄した。その後、純水210mLで5回洗浄を繰り返し、分子末端にクロロホーメート基を有するビスフェノールBオリゴマー、および4,4’-ジヒドロキシジフェニルエーテルオリゴマーの塩化メチレン溶液を得た。得られた溶液のクロロホーメート濃度は1.23モル/L、固形物濃度は0.233kg/L、平均量体数は1.05であった。以後この得られた原料をBDHDE-CFという。
(PC重合体の製造)
メカニカルスターラー、撹拌羽根、邪魔板を装着した反応容器に、製造例2のZOCBP-CF(368mL)と塩化メチレン(82mL)を注入した。これに末端停止剤としてp-tert-ブチルフェノール(以下、PTBPと表記)(0.314g)を添加し、十分に混合されるように撹拌した。反応器内の温度が10℃になるまで冷却した後、この溶液に調製した3,3’-ジメチル-4,4’-ジヒドロキシビフェニルと9-(4-ヒドロキシベンジル)-10-(4-ヒドロキシフェニル)アントラセン溶液(溶液調製法:2.5Nの水酸化カリウム水溶液120mL(水酸化カリウム16.9g)を調製し、室温以下に冷却した後、酸化防止剤としてハイドロサルファイトを0.25g、3,3’-ジメチル-4,4’-ジヒドロキシビフェニル9.0g、および9-(4-ヒドロキシベンジル)-10-(4-ヒドロキシフェニル)アントラセン15.8gを添加し、完全に溶解して調製した)を全量添加し、撹拌しながらトリエチルアミン水溶液(7vol%)を5.4mL添加し、3時間撹拌を継続した。
得られた反応混合物を塩化メチレン1L、水0.1Lで希釈し、洗浄を行った。下層を分離し、さらに水0.25Lで1回、0.03N塩酸0.25Lで1回、水0.25Lで3回の順で洗浄を行った。得られた塩化メチレン溶液を、撹拌下メタノールに滴下投入し、得られた再沈物をろ過、乾燥することにより下記構造のPC重合体(PC-1)を得た。
このようにして得られたPC重合体(PC-1)を塩化メチレンに溶解して、濃度0.5g/dLの溶液を調製し、20℃における還元粘度[ηsp/C]を測定したところ、1.06dL/gであった。なお、得られたPC-1の構造および組成を1H-NMRスペクトルにより分析したところ、下記の繰り返し単位、繰り返し単位数、および組成からなるPC重合体であることが確認された。
なお、還元粘度は、離合社製、自動粘度測定装置VMR-042を用い、自動粘度用ウッベローデ改良型粘度計(RM型)で測定した。1H-NMRスペクトルは、日本電子株式会社製の核磁気共鳴装置JNM-ECZ400Sで測定した。
1H-NMRスペクトルの測定条件は以下の通りである。
・溶媒 :CD2Cl2
・測定濃度(サンプル量/溶媒量):1.5mg/mL
・積算回数:64回(約3min)
共役ジエン基(アントラセン骨格)濃度は、0.71mmol/gである。
(PC重合体の製造)
メカニカルスターラー、撹拌羽根、邪魔板を装着した反応容器に、製造例2のZOCBP-CF(184mL)と塩化メチレン(41mL)を注入した。これに末端停止剤としてN-(4-ヒドロキシフェニル)マレイミド(以下、Male1と表記)(2.968g)を添加し、十分に混合されるように撹拌した。反応器内の温度が10℃になるまで冷却した後、この溶液に調製した3,3’-ジメチル-4,4’-ジヒドロキシビフェニル溶液(溶液調製法:2.5mol/Lの炭酸カリウム水溶液60mL(炭酸カリウム20.9g)を調製し、室温以下に冷却した後、酸化防止剤としてハイドロサルファイトを0.1g、3,3’-ジメチル-4,4’-ジヒドロキシビフェニル7.3gを添加して調製した)を全量添加し、撹拌しながらトリエチルアミン水溶液(7vol%)を2.7mL添加し、3時間撹拌を継続した。
得られた反応混合物を塩化メチレン0.5L、水0.1Lで希釈し、洗浄を行った。下層を分離し、さらに水0.15Lで1回、0.03N塩酸0.15Lで1回、水0.15Lで3回の順で洗浄を行った。得られた塩化メチレン溶液を、撹拌下メタノールに滴下投入し、得られた再沈物をろ過、乾燥することにより下記構造のPC重合体(PC-2)を得た。
このようにして得られたPC重合体(PC-2)を塩化メチレンに溶解して、濃度0.5g/dLの溶液を調製し、20℃における還元粘度[ηsp/C]を測定したところ、0.23dL/gであった。なお、得られたPC-2の構造および組成を1H-NMRスペクトルにより分析したところ、下記の繰り返し単位、繰り返し単位数、および組成からなるPC重合体であることが確認された。
ジエノフィル基(マレイミド基)濃度は、0.39mmol/gである。
(PC重合体の製造)
合成例1で、3,3’-ジメチル-4,4’-ジヒドロキシビフェニルの使用量を13.5gに、9-(4-ヒドロキシベンジル)-10-(4-ヒドロキシフェニル)アントラセンの使用量を7.9gに変更した以外は合成例1と同様にして下記構造のPC重合体(PC-3)を得た。
このようにして得られたPC重合体(PC-3)を塩化メチレンに溶解して、濃度0.5g/dLの溶液を調製し、20℃における還元粘度[ηsp/C]を測定したところ、1.08dL/gであった。なお、得られたPC-3の構造および組成を1H-NMRスペクトルにより分析したところ、下記の繰り返し単位、繰り返し単位数、および組成からなるPC重合体であることが確認された。
共役ジエン基(アントラセン骨格)濃度は、0.39mmol/gである。
(PC重合体の製造)
合成例1で、ZOCBP-CFの代わりに製造例3のOCBP-CF(227mL)に変更し、初期に使用していた塩化メチレン(82mL)を使用せず、PTBPの使用量を0.53gに変更し、3,3’-ジメチル-4,4’-ジヒドロキシビフェニルを使用せず、9-(4-ヒドロキシベンジル)-10-(4-ヒドロキシフェニル)アントラセンの使用量を19.6gに変更し、2.5Nの水酸化カリウム水溶液を75mL(水酸化カリウム10.5g)に変更し、トリエチルアミンの使用量を2.7mLに変更した以外は合成例1と同様にして下記構造のPC重合体(PC-4)を得た。
このようにして得られたPC重合体(PC-4)を塩化メチレンに溶解して、濃度0.5g/dLの溶液を調製し、20℃における還元粘度[ηsp/C]を測定したところ、0.95dL/gであった。なお、得られたPC-4の構造および組成を1H-NMRスペクトルにより分析したところ、下記の繰り返し単位、繰り返し単位数、および組成からなるPC重合体であることが確認された。
共役ジエン基(アントラセン骨格)濃度は、1.44mmol/gである。
(PC重合体の製造)
合成例1で、ZOCBP-CFの代わりに製造例1のZ-CF(76mL)に変更し、初期に使用していた塩化メチレン量を114mLに変更し、PTBPの使用量を0.151gに変更し、3,3’-ジメチル-4,4’-ジヒドロキシビフェニルを使用せず、9-(4-ヒドロキシベンジル)-10-(4-ヒドロキシフェニル)アントラセンの使用量を16.0gに変更し、2.5Nの水酸化カリウム水溶液を2.36Nの水酸化カリウム水溶液65mL(水酸化カリウム8.6g)に変更し、トリエチルアミンの使用量を1.0mLに変更した以外は合成例1と同様にして下記構造のPC重合体(PC-5)を得た。
このようにして得られたPC重合体(PC-5)を塩化メチレンに溶解して、濃度0.5g/dLの溶液を調製し、20℃における還元粘度[ηsp/C]を測定したところ、0.95dL/gであった。なお、得られたPC-5の構造および組成を1H-NMRスペクトルにより分析したところ、下記の繰り返し単位、繰り返し単位数、および組成からなるPC重合体であることが確認された。
共役ジエン基(アントラセン骨格)濃度は、1.44mmol/gである。
(PC重合体の製造)
合成例1で、ZOCBP-CFの代わりに製造例4のBDHDE-CF(87mL)に変更し、初期に使用していた塩化メチレン量を138mLに変更し、PTBPの使用量を0.142gに変更し、3,3’-ジメチル-4,4’-ジヒドロキシビフェニルを4,4’-ジヒドロキシジフェニルエーテル5.3gに変更し、9-(4-ヒドロキシベンジル)-10-(4-ヒドロキシフェニル)アントラセンの使用量を9.8gに変更し、2.5Nの水酸化カリウム水溶液を2.25Nの水酸化カリウム水溶液75mL(水酸化カリウム9.5g)に変更し、トリエチルアミンの使用量を1.0mLに変更した以外は合成例1と同様にして下記構造のPC重合体(PC-6)を得た。
このようにして得られたPC重合体(PC-6)を塩化メチレンに溶解して、濃度0.5g/dLの溶液を調製し、20℃における還元粘度[ηsp/C]を測定したところ、1.25dL/gであった。なお、得られたPC-6の構造および組成を1H-NMRスペクトルにより分析したところ、下記の繰り返し単位、繰り返し単位数、および組成からなるPC重合体であることが確認された。
共役ジエン基(アントラセン骨格)濃度は、0.82mmol/gである。
(PC重合体の製造)
メカニカルスターラー、撹拌羽根、邪魔板を装着した反応容器に、製造例2のZOCBP-CF(184mL)と塩化メチレン(41mL)を注入した。これに末端停止剤としてN-(4-ヒドロキシフェニル)マレイミド(以下、Male1と表記)(0.546g)を添加し、十分に混合されるように撹拌した。反応器内の温度が10℃になるまで冷却した後、2.5mol/Lの炭酸カリウム水溶液10mL(炭酸カリウム3.5g)を添加し、撹拌しながらトリエチルアミン水溶液(7vol%)を2.7mL添加し、30分撹拌した。その後、3,3’-ジメチル-4,4’-ジヒドロキシビフェニル4.5g、および9-(4-ヒドロキシベンジル)-10-(4-ヒドロキシフェニル)アントラセン7.9gを1.7NのNaOH水溶液75mL(NaOHを5.0g使用、ハイドロサルファイトナトリウム100mg添加)に溶解した溶液を全量加え、さらに1時間撹拌した。得られた反応混合物を塩化メチレン0.5L、水0.1Lで希釈し、洗浄を行った。下層を分離し、さらに水0.15Lで1回、0.03N塩酸0.15Lで1回、水0.15Lで3回の順で洗浄を行った。得られた塩化メチレン溶液を、撹拌下メタノールに滴下投入し、得られた再沈物をろ過、乾燥することにより下記構造のPC重合体(PC-7)を得た。
このようにして得られたPC重合体(PC-7)を塩化メチレンに溶解して、濃度0.5g/dLの溶液を調製し、20℃における還元粘度[ηsp/C]を測定したところ、0.66dL/gであった。なお、得られたPC-7の構造および組成を1H-NMRスペクトルにより分析したところ、下記の繰り返し単位、繰り返し単位数、および組成からなるPC重合体であることが確認された。
共役ジエン基(アントラセン骨格)濃度は0.74mmol/gである。
ジエノフィル基(マレイミド骨格)濃度は0.082mmol/gである。
(PC重合体の製造)
合成例1で、ZOCBP-CFの代わりに製造例3のOCBP-CF(112mL)に変更し、初期に使用していた塩化メチレン(82mL)を使用せず、PTBPの使用量を0.21gに変更し、3,3’-ジメチル-4,4’-ジヒドロキシビフェニルを4,4’-ジヒドロキシジフェニルエーテル(DHDE)5.2gに変更し、9-(4-ヒドロキシベンジル)-10-(4-ヒドロキシフェニル)アントラセンの使用量を2.4gに変更し、2.1Nの水酸化カリウム水溶液を50mL(水酸化カリウム5.8g)に変更し、トリエチルアミンの使用量を1.4mLに変更した以外は合成例1と同様にして下記構造のPC重合体(PC-8)を得た。
このようにして得られたPC重合体(PC-8)を塩化メチレンに溶解して、濃度0.5g/dLの溶液を調製し、20℃における還元粘度[ηsp/C]を測定したところ、1.04dL/gであった。なお、得られたPC-8の構造および組成を1H-NMRスペクトルにより分析したところ、下記の繰り返し単位、繰り返し単位数、および組成からなるPC重合体であることが確認された。
共役ジエン基(アントラセン骨格)濃度は、0.46mmol/gである。
(PC重合体の製造)
合成例1で、ZOCBP-CFの代わりに製造例3のOCBP-CF(112mL)に変更し、初期に使用していた塩化メチレン(82mL)を使用せず、PTBPの使用量を0.224gに変更し、3,3’-ジメチル-4,4’-ジヒドロキシビフェニルを1,1-ビス(3-メチル―4-ヒドロキシフェニル)エタン(以下、BisOCEと表記)6.2gに変更し、9-(4-ヒドロキシベンジル)-10-(4-ヒドロキシフェニル)アントラセンの使用量を2.4gに変更し、2.1Nの水酸化カリウム水溶液を50mL(水酸化カリウム5.8g)に変更し、トリエチルアミンの使用量を1.4mLに変更した以外は合成例1と同様にして下記構造のPC重合体(PC-9)を得た。
このようにして得られたPC重合体(PC-9)を塩化メチレンに溶解して、濃度0.5g/dLの溶液を調製し、20℃における還元粘度[ηsp/C]を測定したところ、1.07dL/gであった。なお、得られたPC-9の構造および組成を1H-NMRスペクトルにより分析したところ、下記の繰り返し単位、繰り返し単位数、および組成からなるPC重合体であることが確認された。
共役ジエン基(アントラセン骨格)濃度は、0.39mmol/gである。
(PC重合体の製造)
メカニカルスターラー、撹拌羽根、邪魔板を装着した反応容器に、製造例3のOCBP-CF(57mL)を注入した。これに末端停止剤としてp-tert-ブチルフェノール(以下、PTBPと表記)(0.107g)、および2-(2-フラニルメチル)ヒドロキノン(以下、FRと表記)(2.48g)を添加し、窒素ガスを反応容器の気相に0.2L/分の流速で吹込みながら、十分に混合されるように20分間撹拌した。気相の酸素濃度を溶存酸素計(飯島電子工業株式会社製DOメーターMODEL B-506)のDOモードで読み取った値が0.5mg/L以下になった後、測定プローブを反応溶液に浸漬して液中の酸素濃度を測定し、気相と同様に0.5mg/L以下の読み取り値であることを確認した。反応器内の温度が10℃になるまで冷却した後、2.3Nの炭酸カリウム水溶液(炭酸カリウム1.26gをイオン交換水(4mL)に溶解し、ハイドロサルファイトナトリウム50mgを添加して調製)を加え、撹拌しながらトリエチルアミン水溶液(7vol%)を0.7mL添加し、30分撹拌を継続した。この溶液に1.9Nの水酸化ナトリウム水溶液20mL(水酸化ナトリウム1.5g)を調製し、室温以下に冷却した後、酸化防止剤としてハイドロサルファイトを50mgを添加し、完全に溶解して調製した)を全量添加しさらに30分撹拌を継続した。
得られた反応混合物を窒素雰囲気で、別途窒素置換により酸素濃度を0.1mg/L以下に低減した塩化メチレン200mL、水50mLLで希釈し、洗浄を行った。下層を分離し、さらに水100mLで1回、0.03N塩酸100mLで1回、水100mLで3回の順で洗浄を行った。得られた塩化メチレン溶液を、撹拌下メタノールに滴下投入し、得られた再沈物をろ過、乾燥することにより下記構造のPC重合体(PC-10)を得た。
このようにして得られたPC重合体(PC-10)を塩化メチレンに溶解して、濃度0.5g/dLの溶液を調製し、20℃における還元粘度[ηsp/C]を測定したところ、1.56dL/gであった。なお、得られたPC-10の構造および組成を1H-NMRスペクトルにより分析したところ、下記の繰り返し単位、繰り返し単位数、および組成からなるPC重合体であることが確認された。
フラン基濃度は、1.89mmol/gである。
(PC重合体の製造)
メカニカルスターラー、撹拌羽根、邪魔板を装着した反応容器に、製造例3のOCBP-CF(56mL)を注入した。これに末端停止剤としてp-tert-ブチルフェノール(以下、PTBPと表記)(0.077g)、および1,4-ジヒドロキシアントラセン(以下、1,4ANTと表記)(0.68g)をアセトン5mLに溶解して添加し、窒素ガスを反応容器の気相に0.2L/分の流速で吹込みながら、十分に混合されるように20分間撹拌した。気相の酸素濃度を溶存酸素計(飯島電子工業株式会社製DOメーターMODEL B-506)のDOモードで読み取った値が0.5mg/L以下になった後、測定プローブを反応溶液に浸漬して液中の酸素濃度を測定し、気相と同様に0.5mg/L以下の読み取り値である事を確認した。反応器内の温度が10℃になるまで冷却した後、1.6Nの炭酸カリウム水溶液(炭酸カリウム1.07gをイオン交換水(5mL)に溶解し、ハイドロサルファイトナトリウム50mgを添加して調製)を加え、撹拌しながらトリエチルアミン水溶液(7vol%)を0.7mL添加し、30分撹拌を継続した。この溶液に調製した1,1-ビス(3-メチル-4-ヒドロキシフェニル)エタン(3.1g)溶液(溶液調製法:2.4Nの水酸化ナトリウム水溶液16mL(水酸化ナトリウム1.5g)を調製し、10℃以下に冷却した後、酸化防止剤としてハイドロサルファイトを50mgを添加し、完全に溶解して調製した)を全量添加しさらに2時間30分撹拌を継続した。
得られた反応混合物を窒素雰囲気で、別途窒素置換により酸素濃度を0.1mg/L以下に低減した塩化メチレン200mL、水50mLLで希釈し、洗浄を行った。下層を分離し、さらに水100mLで1回、0.03N塩酸100mLで1回、水100mLで3回の順で洗浄を行った。得られた塩化メチレン溶液を、撹拌下メタノールに滴下投入し、得られた再沈物をろ過、乾燥することにより下記構造のPC重合体(PC-11)を得た。
このようにして得られたPC重合体(PC-1)を塩化メチレンに溶解して、濃度0.5g/dLの溶液を調製し、20℃における還元粘度[ηsp/C]を測定したところ、0.72dL/gであった。なお、得られたPC-11の構造および組成を1H-NMRスペクトルにより分析したところ、下記の繰り返し単位、繰り返し単位数、および組成からなるPC重合体であることが確認された。
アントラセン基濃度は、0.49mmol/gである。
(PC重合体の製造)
合成例8で、OCBP-CF使用量を29.2mLに変更し、塩化メチレン(16mL)を加え、PTBPの代わりに9-(4-ヒドロキシフェニル)アントラセンを0.049g使用し、4,4’-ジヒドロキシジフェニルエーテル(DHDE)1.23gに変更し、9-(4-ヒドロキシベンジル)-10-(4-ヒドロキシフェニル)アントラセン(以下、ANT1と表記)の使用量を0.57gに変更し、2.1Nの水酸化カリウム水溶液を12mL(水酸化カリウム1.4g)に変更し、トリエチルアミンの使用量を0.3mLに変更した以外は合成例8と同様にして下記構造のPC重合体(PC-12)を得た。
このようにして得られたPC重合体(PC-12)を塩化メチレンに溶解して、濃度0.5g/dLの溶液を調製し、20℃における還元粘度[ηsp/C]を測定したところ、1.37dL/gであった。なお、得られたPC-12の構造および組成を1H-NMRスペクトルにより分析したところ、下記の繰り返し単位、繰り返し単位数、および組成からなるPC重合体であることが確認された。
共役ジエン基(アントラセン骨格)濃度は、0.46mmol/gである。
(PAR重合体の製造)
合成例12で、OCBP-CFの代わりに4,4’-ビフェニルジカルボン酸クロリド(DPE)(東京化成社製)2.2gを使用し、塩化メチレンの使用量を200mLに変更し、PTBPの代わりに2,3,5-トリメチルフェノールを0.01g使用し、4,4’-ジヒドロキシジフェニルエーテル(DHDE)の代わりに1,1-Bis(3-メチル-4-ヒドロキシフェニル)エタン0.56gに変更し、2.1Nの水酸化カリウム水溶液を0.15Nの水酸化カリウム水溶液15mL(水酸化カリウム1.3g)に変更し、トリエチルアミンの使用量を0.5mLに変更した以外は合成例12と同様にして下記構造のポリアリレート重合体(PAR-1)を得た。
このようにして得られたPC重合体(PAR-1)を塩化メチレンに溶解して、濃度0.5g/dLの溶液を調製し、20℃における還元粘度[ηsp/C]を測定したところ、0.27dL/gであった。なお、得られたPAR-1の構造および組成を1H-NMRスペクトルにより分析したところ、下記の繰り返し単位、繰り返し単位数、および組成からなるPAR重合体であることが確認された。
共役ジエン基(アントラセン骨格)濃度は、0.52mmol/gである。
<共役ジエン基を持つポリカーボネートとジエノフィル基を持つポリカーボネートからなる塗液組成物の調製と、架橋樹脂フィルムの調製>
PC-1を1.5gと、PC-2を0.3gとをスクリューキャップ付きのサンプルチューブに計り取り、テトラヒドロフラン10mLに溶解して、塗液組成物を得た。得られた塗液組成物を、ギャップ200μmのアプリケーターを用い、50μm厚のポリイミドフィルムにキャスト成膜した。1時間風乾した後、真空乾燥機で温度50℃、16時間処理し、溶剤を除去して、前駆体フィルムを得た。
得られた前駆体フィルムを減圧乾燥機(減圧度は1~100Pa)にて温度200℃で、3時間加熱して架橋処理して、樹脂フィルムを得た。
<共役ジエン基を持つポリカーボネートとジエノフィル基を持つポリカーボネートと電荷輸送物質とからなる電荷輸送層用の塗液組成物の調製と、架橋樹脂フィルムの調製>
PC-1を1.25gと、PC-2を0.25gと、電荷輸送物質(CTM-1)を1.0gとをスクリューキャップ付きのサンプルチューブに計り取り、テトラヒドロフラン10mLに溶解して、塗液組成物を得た。得られた塗液組成物を、ギャップ200μmのアプリケーターを用い、50μm厚のポリイミドフィルムにキャスト成膜した。1時間風乾した後、真空乾燥機で温度50℃、16時間処理し、溶剤を除去して、前駆体フィルムを得た。
得られた前駆体フィルムを減圧乾燥機(減圧度は1~100Pa)にて温度150℃で、3時間加熱して架橋処理して、樹脂フィルムを得た。
実施例1でPC-2を使用しない以外は実施例1と同様にして樹脂フィルム(摩耗試験用)を得た。
実施例2でPC-2を使用せず、PC-1の使用量を1.5gに変更した以外は実施例2と同様にして、塗液組成物および樹脂フィルム(摩耗試験用、および電気特性評価用)を得た。
実施例1でPC-1およびPC-2を使用せず、下記構造のポリカーボネート樹脂(使用量1.5g)を使用した以外は実施例1と同様にして、樹脂フィルム(摩耗試験用)を得た。
実施例2でPC-1およびPC-2を使用せず、比較例100で用いたポリカーボネート樹脂(使用量1.5g)を使用した以外は実施例2と同様にして、塗液組成物および樹脂フィルム(摩耗試験用、および電気特性評価用)を得た。
架橋処理後の樹脂フィルムを剥離し、塩化メチレン中に投入し、外観を確認した。得られた結果を表1に示す。
耐溶剤性の評価の詳細は、以下の通りである。厚さ20~30μmのフィルムを1cm×2cmの長方形に切り出してサンプルを作製した。サンプルを8mLのサンプルチューブに入れた。続いて、サンプルチューブに塩化メチレンを8mL入れ、サンプルを塩化メチレン中に完全に浸漬した。振とう機を用い、サンプルチューブを室温で1時間、振とう速度120rpmで振とうした後、外観を確認した。
評価基準は以下の通りである。
D(溶解):目視で不溶分無し。
C(小間切):細切れの不溶分は有るが、大部分は溶解した。
B(膨潤):不溶分はひと塊だが、溶剤膨潤によりフィルム形状を保っていない。
A(不溶):膨潤無いか、僅かな膨潤でフィルム形状を保っている。
樹脂フィルムのキャスト面の耐摩耗性をスガ摩耗試験機NUS-ISO-3型(スガ試験機社製)を用いて評価した。試験条件は4.9Nの荷重をかけた摩耗紙(粒径3μmのアルミナ粒子を含有)をキャスト面(感光層表面を模した面)と接触させて2,000回往復運動を行い、質量減少量(摩耗量)を測定した。得られた結果を表1に示す。
導電性基体として膜厚100μmのアルミニウム板を用い、その表面に、電荷発生層と電荷輸送層を順次積層して積層型感光層を形成した電子写真感光体を製造した。電荷発生物質としてY型オキソチタニウムフタロシアニン0.5質量部を用い、バインダー樹脂としてブチラール樹脂0.5質量部を用いた。これらを溶媒のTHF19質量部に加え、ボールミルにて分散し、この分散液をバーコーターにより、前記導電性基体フィルム表面に塗工し、70℃、30分間乾燥させることにより、膜厚約0.5μmの電荷発生層を形成した。
つぎに、電荷輸送層用の塗液組成物として、実施例2において、CTM-1の使用量を0.75gに変更した以外は同様に得られた塗液組成物をギャップ200μmのアプリケーターにより、前記電荷発生層の上に塗布し、温度50℃で8時間、その後、温度100℃8時間、減圧乾燥(減圧度は1~100Pa)し、膜厚約30μmの電荷輸送層を形成した。得られた感光体フィルムを温度150℃で、3時間加熱することで感光体を得た。
得られた電子写真感光体フィルムをφ60mmのアルミドラムに貼りつけ、電子写真特性を静帯電試験装置CYNTHIA54IM(ジェンテック株式会社製)を用い、EVモードにて表面電位の光減衰特性を評価した。なお、初期帯電量は、-750Vとした。
得られた結果を図1に示す。
また、比較例2および比較例101で得られた塗液組成物についても、上記と同様にして、表面電位の光減衰特性を評価した。得られた結果を図1に示す。
PC-5(組成比(モル%)が、BisZ:BIPANT=6:4である共役ジエン)を1.5gと、ジエノフィルとして、下記式(MI-BisA)で表される2,2-ビス[4-(4-マレイミドフェノキシ)フェニル]プロパン(以下、MI-BisAと表記)を0.56gとをスクリューキャップ付きのサンプルチューブに計り取り、テトラヒドロフラン10mLに溶解して、塗液組成物を得た。得られた塗液組成物を、ギャップ200μmのアプリケーターを用い、50μm厚のポリイミドフィルムにキャスト成膜した。1時間風乾した後、真空乾燥機で温度50℃、16時間処理し、溶剤を除去して、前駆体フィルムを得た。
得られた前駆体フィルムを減圧乾燥機(減圧度は1~100Pa)にて温度200℃で、3時間加熱して架橋処理して、樹脂フィルムを得た。そして、得られた樹脂フィルムについて、前述の方法で、耐溶剤性(塩化メチレン溶解性)および耐摩耗性の評価を行った。得られた結果を表2に示す。
共役ジエンと、ジエノフィルと、電荷輸送物質とを下記表2に示す通りとし、さらに加熱条件を下記表2に示す通りとした以外は実施例3と同様にして、樹脂フィルムを得た。そして、得られた樹脂フィルムについて、前述の方法で、耐溶剤性および耐摩耗性の評価を行った。得られた結果を表2に示す。
なお、電荷輸送物質(CTM-2)は、以下に示す混合物である。
実施例3でMI-BisAを使用せず、加熱条件を100℃で3時間に変更した以外は実施例3と同様にして、樹脂フィルムを得た。そして、得られた樹脂フィルムについて、前述の方法で、耐溶剤性および耐摩耗性の評価を行った。得られた結果を表2に示す。
共役ジエンと、ジエノフィルと、電荷輸送物質とを下記表2に示す通りとし、さらに加熱条件を下記表2に示す通りとした以外は、比較例3-1と同様にして、樹脂フィルムを得た。そして、得られた樹脂フィルムについて、前述の方法で、耐溶剤性および耐摩耗性の評価を行った。得られた結果を表2に示す。
共役ジエンと、ジエノフィルと、電荷輸送物質とを下記表3に示す通りとし、さらに加熱条件を下記表3に示す通りとし、摩耗試験の繰返し数を800回に変更した以外は実施例3と同様にして、樹脂フィルムを得た。そして、得られた樹脂フィルムについて、前述の方法で、耐溶剤性および耐摩耗性の評価を行った。得られた結果を表3に示す。
共役ジエンと、ジエノフィルと、電荷輸送物質とを下記表3に示す通りとし、さらに加熱条件を下記表3に示す通りとし、摩耗試験の繰返し数を800回に変更した以外は、比較例3-1と同様にして、樹脂フィルムを得た。そして、得られた樹脂フィルムについて、前述の方法で、耐溶剤性および耐摩耗性の評価を行った。得られた結果を表3に示す。
<共役ジエン基を持つポリアリレートとジエノフィル基を持つポリカーボネートからなる塗液組成物の調製と、架橋樹脂フィルムの調製>
PAR-1を1.2gと、PC-2を0.3gとをスクリューキャップ付きのサンプルチューブに計り取り、テトラヒドロフラン10mLに溶解して、塗液組成物を得た。得られた塗液組成物を、ギャップ200μmのアプリケーターを用い、250μm厚のPETフィルムにキャスト成膜した。1時間風乾した後、真空乾燥機で温度50℃、16時間処理し、溶剤を除去して、前駆体フィルムを得た。
得られた前駆体フィルムを減圧乾燥機(減圧度は1~100Pa)にて温度200℃で、1時間加熱して架橋処理して、樹脂フィルムを得た。
<共役ジエン基を持つポリアリレートとジエノフィル基を持つポリカーボネートと電荷輸送物質とからなる電荷輸送層用の塗液組成物の調製と、架橋樹脂フィルムの調製>
PAR-1を1.25gと、PC-2を0.25gと、電荷輸送物質(CTM-1)を1.0gとをスクリューキャップ付きのサンプルチューブに計り取り、テトラヒドロフラン10mLに溶解して、塗液組成物を得た。得られた塗液組成物を、ギャップ200μmのアプリケーターを用い、250μm厚のPETフィルムにキャスト成膜した。1時間風乾した後、真空乾燥機で温度50℃、16時間処理し、溶剤を除去して、前駆体フィルムを得た。
得られた前駆体フィルムを減圧乾燥機(減圧度は1~100Pa)にて温度150℃で、1時間加熱して架橋処理して、樹脂フィルムを得た。
実施例18でPC-2を使用せず、PAR-1の使用量を1.5gに変更した以外は実施例18と同様にして樹脂フィルムを得た。
実施例19でPC-2を使用せず、PAR-1の使用量を1.5gに変更した以外は実施例2と同様にして、塗液組成物および樹脂フィルムを得た。
実施例3で得られた前駆体フィルムを剥離し、下記の測定条件で、DSC(パーキンエルマー製、「diamond DSC」)測定を行った。得られた結果を図2に示す。
昇温速度:5℃/分測定範囲:温度50℃から300℃まで昇温
使用機器:JASCO社製「FP-8600」
励起波長:300~500nm
蛍光波長:300~600nm
データ取込間隔:(励起)5nm,(蛍光)4nm
感度:high
蛍光バンド:5.0nm
励起バンド幅:5.0nm
レスポンス:0.5sec
走査速度:500nm/min
測定方法:フィルムをスライドガラスに張り付けた状態で、光源およびディテクターに対して45°の角度になるように配置し測定した。
比較例3-1に示した樹脂膜は、アントラセン骨格に特有の蛍光が見られるが、実施例1のマレイミド基を持つPCと混合したフィルムでは、溶剤除去の乾燥条件(50℃、16時間)でも蛍光発光強度が大幅に低下した。さらに200℃で3時間加熱処理することで蛍光は見られなくなった。このことから、アントラセン骨格が反応により蛍光を持たない骨格に変換されていることが確認された。
実施例3で得られた200℃で3時間加熱処理した後のフィルムを剥離し、アルカリ条件でカーボネート結合を加水分解し、断片化した成分をLC-MSにより分析した。
試料0.05gを塩化メチレン15mLに溶解後、1N-KOH/メタノール3mLを加えた。溶液を30min攪拌後、40℃で窒素ブローして溶媒を乾固させ、イオン交換水を10mLで試料を溶解し、2N-HClにて中和した。アセトニトリルで50mLに定容し、固形物は0.45μmクロマトディスクにて除去した。そして、得られた試料を下記条件でLC-MS測定した。
装置:
LC部(Waters社製 UPLC Hclass)
MS部(Waters社製 XevoG2XS Qtof)
カラム:BEH C18(1.7μm×2.1mm×50mm)
カラム温度:40℃
注入量:1.0μL
流速:0.50mL/分
展開溶媒:
0~2分 酢酸アンモニウム水溶液(0.2モル/L):アセトニトリル=7:3
2~6分 酢酸アンモニウム水溶液(0.2モル/L):アセトニトリル=7:3
6~8分 酢酸アンモニウム水溶液(0.2モル/L):アセトニトリル=3:7
8~8.5分 酢酸アンモニウム水溶液(0.2モル/L):アセトニトリル:THF=5:45:50
8.5分~最終 酢酸アンモニウム水溶液(0.2モル/L):アセトニトリル=7:3
MS条件
イオン化法:ESI±
質量範囲:50~1500
溶出時間7.3~7.6の成分に、質量1323.48である下記推定構造の化合物に由来するマスピークが検出された。
以上のこと、およびディールス・アルダー反応に関する一般的な反応形態から、架橋前駆体組成物を加熱した際には下記のような架橋構造を有する樹脂が生成していることが確認された。
Claims (25)
- 芳香族ポリカーボネートおよびポリアリレートからなる群から選択される少なくとも1つの樹脂であって、
前記樹脂は、ディールス・アルダー反応による高分子鎖間の結合を有する、
ことを特徴とする樹脂。 - 請求項1に記載の樹脂において、
前記高分子鎖間の結合は、高分子鎖に2つ以上の共役ジエン構造を持つ高分子と、2官能以上のジエノフィル基を持つ化合物との反応による、
ことを特徴とする樹脂。 - 請求項1に記載の樹脂において、
前記高分子鎖間の結合は、高分子鎖に2つ以上のジエノフィル構造を持つ高分子と、2官能以上の共役ジエン基を持つ化合物との反応による、
ことを特徴とする樹脂。 - 請求項1に記載の樹脂において、
前記高分子鎖間の結合は、高分子鎖に2つ以上の共役ジエン構造を持つ高分子と、高分子鎖に2つ以上のジエノフィル構造を持つ高分子との反応による、
ことを特徴とする樹脂。 - 請求項2から請求項4のいずれか一項に記載の樹脂において、
前記高分子は、高分子鎖の末端に、共役ジエン構造およびジエノフィル構造の少なくとも一方を2つ以上持たない、
ことを特徴とする樹脂。 - 請求項2から請求項5のいずれか一項に記載の樹脂において、
前記高分子は、前記高分子鎖の主鎖中に、共役ジエン構造およびジエノフィル構造の少なくとも一方を1つ以上持つ、
ことを特徴とする樹脂。 - 請求項1に記載の樹脂において、
前記高分子鎖間の結合は、下記(iii-1)~(iii-8)の少なくともいずれかの反応による、
ことを特徴とする樹脂。
(iii-1)2つのジエノフィル構造を有する高分子であって、高分子鎖の両末端に当該ジエノフィル構造を1つずつ有する高分子と、
高分子鎖に2つを超える共役ジエン構造を有する高分子と、の反応
(iii-2)2つのジエノフィル構造を有する高分子であって、高分子鎖の両末端に当該ジエノフィル構造を1つずつ有する高分子と、
高分子鎖に2つを超える共役ジエン構造を有する高分子であって、当該高分子鎖の両末端に当該共役ジエン構造を1つずつ有し、かつ主鎖内にも当該共役ジエン構造を1以上有する高分子と、の反応
(iii-3)2つのジエノフィル構造を有する高分子であって、高分子鎖の両末端に当該ジエノフィル構造を1つずつ有する高分子と、
高分子鎖に2つを超える共役ジエン構造を有する高分子であって、当該高分子鎖の一方の末端に当該共役ジエン構造を1つ有し、他方の末端には当該共役ジエン構造を有さず、かつ主鎖内に当該共役ジエン構造を2つ以上有する高分子と、の反応
(iii-4)2つのジエノフィル構造を有する高分子であって、高分子鎖の両末端に当該ジエノフィル構造を1つずつ有する高分子と、
高分子鎖の両末端には共役ジエン構造を有さず、かつ主鎖内に2つを超える共役ジエン構造を有する高分子と、の反応
(iii-5)2つの共役ジエン構造を有する高分子であって、高分子鎖の両末端に当該共役ジエン構造を1つずつ有する高分子と、
高分子鎖に2つを超えるジエノフィル構造を有する高分子との反応
(iii-6)2つの共役ジエン構造を有する高分子であって、高分子鎖の両末端に当該共役ジエン構造を1つずつ有する高分子と、
高分子鎖に2つを超えるジエノフィル構造を有する高分子であって、当該高分子鎖の両末端にジエノフィル構造を1つずつ有し、かつ主鎖内にもジエノフィル構造を1つ以上有する高分子と、の反応
(iii-7)2つの共役ジエン構造を有する高分子であって、高分子鎖の両末端に当該共役ジエン構造を1つずつ有する高分子と、
高分子鎖に2つを超えるジエノフィル構造を有する高分子であって、当該高分子鎖の一方の末端にジエノフィル構造を1つ有し、他方の末端にはジエノフィル構造を有さず、かつ主鎖内にジエノフィル構造を2つ以上有する高分子と、の反応
(iii-8)2つの共役ジエン構造を有する高分子であって、高分子鎖の両末端に当該共役ジエン構造を1つずつ有する高分子と、
高分子鎖の両末端にはジエノフィル構造を有さず、かつ主鎖内に2つを超えるジエノフィル構造を有する高分子と、の反応 - 請求項1に記載の樹脂において、
前記高分子鎖間の結合は、一本の高分子鎖に共役ジエン構造およびジエノフィル構造の双方の構造を持ち、高分子鎖一本当たりの前記共役ジエン構造および前記ジエノフィル構造それぞれの平均個数が1以上である高分子の反応による、
ことを特徴とする樹脂。 - 請求項8に記載の樹脂において、
前記高分子は、高分子鎖の末端に、共役ジエン構造およびジエノフィル構造の少なくとも一方を2つ以上持たない、
ことを特徴とする樹脂。 - 請求項8または請求項9に記載の樹脂において、
前記高分子は、前記高分子鎖の主鎖中に、共役ジエン構造およびジエノフィル構造の少なくとも一方を1つ以上持つ、
ことを特徴とする樹脂。 - 請求項2から請求項10のいずれか一項に記載の樹脂において、
前記共役ジエン構造または前記共役ジエン基は、下記一般式(DE1)および一般式(DE2)で表される構造の少なくともいずれかの構造を含む、
ことを特徴とする樹脂。
(前記一般式(DE1)および一般式(DE2)において、
R1は、各々独立に、
単結合、
他の骨格との結合基、
水素原子、
炭素数1以上、12以下の脂肪族炭化水素基、
環形成炭素数6以上、12以下の芳香族炭化水素基、または
炭素数1以上、10以下のアルコキシ基であり、
R1のうち1つ、または2つは、単結合、または他の骨格との連結基であり、
当該連結基としてのR1は、炭素原子、酸素原子、窒素原子、硫黄原子、ケイ素原子、リン原子およびホウ素原子からなる群から選択される少なくともいずれかの原子を含み、連結基を構成する原子同士の結合様式が全て共有結合からなる基であり、
複数のR1が連結された環状構造(芳香族環、および複素環を含む)を形成してもよい。) - 請求項11に記載の樹脂において、
前記共役ジエン構造または前記共役ジエン基は、下記一般式(DE3)から一般式(DE8)で表される構造の少なくともいずれかの構造を含む、
ことを特徴とする樹脂。
(前記一般式(DE3)から一般式(DE8)において、
X1は、各々独立に、
-O-、
-(C=O)-O-、
-O-(C=O)-O-、
-O-(C=O)-、または
-S-であり、
R11は、各々独立に、
水素原子、
炭素数1以上、12以下の脂肪族炭化水素基、
環形成炭素数6以上、12以下の芳香族炭化水素基、または
炭素数1以上、10以下のアルコキシ基であり、
複数のR11が連結された環状構造(芳香族環、および複素環を含む)を形成してもよく、
R12は、各々独立に、
水素原子、
炭素数1以上、12以下の脂肪族炭化水素基、または
炭素数6以上、12以下の芳香族炭化水素基であり、
nは、0、または置換可能な数を上限とした自然数を表す。) - 請求項11に記載の樹脂において、
前記共役ジエン構造または前記共役ジエン基は、下記一般式(DE17)および一般式(DE18)で表される構造の少なくともいずれかの構造を含む、
ことを特徴とする樹脂。
(前記一般式(DE17)および一般式(DE18)において、
R11は、各々独立に、
炭素数1以上、12以下の脂肪族炭化水素基、
環形成炭素数6以上、12以下の芳香族炭化水素基、または
炭素数1以上、10以下のアルコキシ基であり、
複数のR11が連結された環状構造(芳香族環、および複素環を含む)を形成してもよく、
前記一般式(DE17)において、
mは、0以上、8以下の整数を表し、
前記一般式(DE18)において、
nは、0以上、4以下の整数を表し、
mは、0以上、9以下の整数を表す。) - 請求項1から請求項18のいずれか一項に記載の樹脂において、
下記一般式(UN1)および一般式(UN2)で表される構造の少なくともいずれかの構造を含む、
ことを特徴とする樹脂。
(前記一般式(UN1)および一般式(UN2)において、Ar3、Ar31およびAr32は、各々独立に、下記一般式(UN11)で表される基である。)
(前記一般式(UN11)において、
m3は、0、1または2であり、
n3は、4であり、
複数のR3は、各々独立に
水素原子、
ハロゲン原子、
炭素数1以上、10以下のアルキル、
環形成炭素数6以上、12以下のアリール、または
炭素数1以上、10以下のフッ化アルキルであり、
X3は、各々独立に、
単結合、
-C(-R31)2-、
-O-、
-S-、
-SO-、
-SO2-、
-N(-R32)-,
-P(-R33)-、
-P=O(-R34)-、
カルボニル、
エステル、
アミド、
炭素数2以上、20以下のアルキレン、
炭素数2以上、20以下のアルキリデン、
環形成炭素数3以上、20以下のシクロアルキレン、
環形成炭素数3以上、20以下のシクロアルキリデン、
環形成炭素数6以上、20以下のアリーレン、
環形成炭素数4以上、20以下のビシクロアルカンジイル、
環形成炭素数5以上、20以下のトリシクロアルカンジイル、
環形成炭素数4以上、20以下のビシクロアルキリデン、および
環形成炭素数5以上、20以下のトリシクロアルキリデンからなる群から選択される1種または2種以上からなる基であり、
R31からR34は、各々独立に、
水素原子、
ハロゲン原子、
炭素数1以上、10以下のアルキル、
環形成炭素数6以上、12以下のアリール、または
炭素数1以上、10以下のフッ化アルキルである。) - 架橋反応により、請求項1から請求項19のいずれか一項に記載の樹脂を作製できる、
ことを特徴とする樹脂前駆体組成物。 - 請求項20に記載の樹脂前駆体組成物と、有機溶剤とを含む、
ことを特徴とする塗液組成物。 - 請求項1から請求項19のいずれか一項に記載の樹脂を最外層に含む、
ことを特徴とする電子写真感光体。 - 請求項21に記載の塗液組成物を湿式成形法で導電性基体に塗布する工程と、
加熱を行うことにより、前記塗液組成物中の有機溶剤を除去する工程と、
前記有機溶剤を除去する工程における加熱と同時、または引き続き加熱を行うことにより、前記塗液組成物中の樹脂前駆体組成物の架橋反応を行う工程と、を備える、
ことを特徴とする電子写真感光体の製造方法。 - 請求項1から請求項19のいずれか一項に記載の樹脂を含む、
ことを特徴とする成形物。 - 請求項1から請求項19のいずれか一項に記載の樹脂を含む、
ことを特徴とする電子デバイス。
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202180025969.2A CN115397886A (zh) | 2020-04-01 | 2021-04-01 | 树脂、树脂前体组合物、涂布液组合物、电子照相感光体、成形物、电子器件和电子照相感光体的制造方法 |
EP21780035.8A EP4130097A4 (en) | 2020-04-01 | 2021-04-01 | RESIN, RESIN PRECURSOR COMPOSITION, COATING COMPOSITION, ELECTROPHOTOGRAPHIC PHOTORECEPTOR, MOLDED BODY, ELECTRONIC DEVICE AND ELECTROPHOTOGRAPHIC PHOTORECEPTOR MANUFACTURING METHOD |
US17/915,584 US20230340194A1 (en) | 2020-04-01 | 2021-04-01 | Resin, resin precursor composition, coating composition, electrophotographic photoreceptor, molded article, electronic device, and electrophotographic photoreceptor production method |
JP2022512703A JPWO2021201228A1 (ja) | 2020-04-01 | 2021-04-01 | |
KR1020227036081A KR20220164515A (ko) | 2020-04-01 | 2021-04-01 | 수지, 수지 전구체 조성물, 도액 조성물, 전자 사진 감광체, 성형물, 전자 디바이스, 및 전자 사진 감광체의 제조 방법 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2020-065625 | 2020-04-01 | ||
JP2020065625 | 2020-04-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2021201228A1 true WO2021201228A1 (ja) | 2021-10-07 |
Family
ID=77929212
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2021/014164 WO2021201228A1 (ja) | 2020-04-01 | 2021-04-01 | 樹脂、樹脂前駆体組成物、塗液組成物、電子写真感光体、成形物、電子デバイス、および電子写真感光体の製造方法 |
Country Status (7)
Country | Link |
---|---|
US (1) | US20230340194A1 (ja) |
EP (1) | EP4130097A4 (ja) |
JP (1) | JPWO2021201228A1 (ja) |
KR (1) | KR20220164515A (ja) |
CN (1) | CN115397886A (ja) |
TW (1) | TW202146520A (ja) |
WO (1) | WO2021201228A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2022211100A1 (ja) * | 2021-04-01 | 2022-10-06 | 出光興産株式会社 | 樹脂、樹脂組成物、塗液組成物、フィルム、コーティング膜、電子写真感光体、絶縁材料、成形物、電子デバイス、および樹脂の製造方法 |
Citations (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3435003A (en) | 1966-06-01 | 1969-03-25 | Du Pont | Cross-linked thermally reversible polymers produced from condensation polymers with pendant furan groups cross-linked with maleimides |
JPH09319102A (ja) | 1996-05-28 | 1997-12-12 | Idemitsu Kosan Co Ltd | 電子写真感光体 |
JPH1077338A (ja) | 1996-08-30 | 1998-03-24 | Idemitsu Kosan Co Ltd | ポリカーボネート樹脂及びその製造方法 |
JPH11172003A (ja) | 1997-12-12 | 1999-06-29 | Idemitsu Kosan Co Ltd | 架橋ポリカーボネート樹脂の製造法および架橋ポリカーボネート樹脂ならびに電子写真感光体 |
JP2000044668A (ja) | 1998-07-30 | 2000-02-15 | Idemitsu Kosan Co Ltd | 架橋ポリカーボネート樹脂組成物とそれを用いた吸収剤およびカラム充填剤 |
JP2003286347A (ja) | 2002-03-28 | 2003-10-10 | Toray Ind Inc | 鎖状熱可塑性樹脂およびその製造方法 |
JP2005139339A (ja) | 2003-11-07 | 2005-06-02 | Kyocera Mita Corp | ポリカーボネート樹脂、電子写真感光体および画像形成装置 |
WO2005056642A1 (ja) * | 2003-12-12 | 2005-06-23 | Nec Corporation | 再成形可能かつ形状回復能に優れた形状記憶性樹脂および該樹脂の架橋物からなる成形体 |
JP2007314719A (ja) | 2006-05-29 | 2007-12-06 | Teijin Chem Ltd | 架橋ポリカーボネート樹脂組成物及びフィルム |
JP2010072019A (ja) | 2008-09-16 | 2010-04-02 | Ricoh Co Ltd | 電子写真感光体、及びそれを用いた電子写真方法、電子写真装置、電子写真装置用プロセスカートリッジ |
JP2012224569A (ja) | 2011-04-18 | 2012-11-15 | Asahi Organic Chemicals Industry Co Ltd | アントラセン誘導体及びこの製造方法、硬化性組成物並びに硬化物 |
JP2013519764A (ja) * | 2010-02-16 | 2013-05-30 | エボニック レーム ゲゼルシャフト ミット ベシュレンクテル ハフツング | 可逆的な架橋を有する機能材料 |
CN103373950A (zh) * | 2012-04-11 | 2013-10-30 | 中国科学院理化技术研究所 | 含有马来酰亚胺基基团的双酚单体及其合成方法和用途 |
CN110092720A (zh) * | 2019-04-29 | 2019-08-06 | 中国科学院理化技术研究所 | 一种含有蒽基基团的双酚羟基单体及其合成方法和应用 |
JP2020509140A (ja) * | 2017-03-07 | 2020-03-26 | ソルベイ スペシャルティ ポリマーズ ユーエスエー, エルエルシー | 芳香族ポリマーのブレンド及びそれから得られる付加物 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7390857B2 (en) * | 2004-08-27 | 2008-06-24 | General Electric Company | Crosslinkable and crosslinked polymers |
CN102482245B (zh) * | 2009-09-11 | 2015-05-13 | 株式会社理光 | 呋喃衍生物和电子照相光电导体 |
US10239865B2 (en) * | 2015-01-15 | 2019-03-26 | Council Of Scientific & Industrial Research | Bisphenols containing pendant clickable maleimide group and polymers therefrom |
CN105153409B (zh) * | 2015-10-16 | 2017-03-22 | 浙江大学 | 一种具有热可逆化学交联特性的热塑性共聚酯组合物及其制备和应用 |
-
2021
- 2021-04-01 WO PCT/JP2021/014164 patent/WO2021201228A1/ja unknown
- 2021-04-01 KR KR1020227036081A patent/KR20220164515A/ko active Search and Examination
- 2021-04-01 JP JP2022512703A patent/JPWO2021201228A1/ja active Pending
- 2021-04-01 US US17/915,584 patent/US20230340194A1/en active Pending
- 2021-04-01 CN CN202180025969.2A patent/CN115397886A/zh active Pending
- 2021-04-01 EP EP21780035.8A patent/EP4130097A4/en active Pending
- 2021-04-01 TW TW110112194A patent/TW202146520A/zh unknown
Patent Citations (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3435003A (en) | 1966-06-01 | 1969-03-25 | Du Pont | Cross-linked thermally reversible polymers produced from condensation polymers with pendant furan groups cross-linked with maleimides |
JPH09319102A (ja) | 1996-05-28 | 1997-12-12 | Idemitsu Kosan Co Ltd | 電子写真感光体 |
JPH1077338A (ja) | 1996-08-30 | 1998-03-24 | Idemitsu Kosan Co Ltd | ポリカーボネート樹脂及びその製造方法 |
JPH11172003A (ja) | 1997-12-12 | 1999-06-29 | Idemitsu Kosan Co Ltd | 架橋ポリカーボネート樹脂の製造法および架橋ポリカーボネート樹脂ならびに電子写真感光体 |
JP2000044668A (ja) | 1998-07-30 | 2000-02-15 | Idemitsu Kosan Co Ltd | 架橋ポリカーボネート樹脂組成物とそれを用いた吸収剤およびカラム充填剤 |
JP2003286347A (ja) | 2002-03-28 | 2003-10-10 | Toray Ind Inc | 鎖状熱可塑性樹脂およびその製造方法 |
JP2005139339A (ja) | 2003-11-07 | 2005-06-02 | Kyocera Mita Corp | ポリカーボネート樹脂、電子写真感光体および画像形成装置 |
WO2005056642A1 (ja) * | 2003-12-12 | 2005-06-23 | Nec Corporation | 再成形可能かつ形状回復能に優れた形状記憶性樹脂および該樹脂の架橋物からなる成形体 |
JP2007314719A (ja) | 2006-05-29 | 2007-12-06 | Teijin Chem Ltd | 架橋ポリカーボネート樹脂組成物及びフィルム |
JP2010072019A (ja) | 2008-09-16 | 2010-04-02 | Ricoh Co Ltd | 電子写真感光体、及びそれを用いた電子写真方法、電子写真装置、電子写真装置用プロセスカートリッジ |
JP2013519764A (ja) * | 2010-02-16 | 2013-05-30 | エボニック レーム ゲゼルシャフト ミット ベシュレンクテル ハフツング | 可逆的な架橋を有する機能材料 |
JP2012224569A (ja) | 2011-04-18 | 2012-11-15 | Asahi Organic Chemicals Industry Co Ltd | アントラセン誘導体及びこの製造方法、硬化性組成物並びに硬化物 |
CN103373950A (zh) * | 2012-04-11 | 2013-10-30 | 中国科学院理化技术研究所 | 含有马来酰亚胺基基团的双酚单体及其合成方法和用途 |
JP2020509140A (ja) * | 2017-03-07 | 2020-03-26 | ソルベイ スペシャルティ ポリマーズ ユーエスエー, エルエルシー | 芳香族ポリマーのブレンド及びそれから得られる付加物 |
CN110092720A (zh) * | 2019-04-29 | 2019-08-06 | 中国科学院理化技术研究所 | 一种含有蒽基基团的双酚羟基单体及其合成方法和应用 |
Non-Patent Citations (2)
Title |
---|
MACROMOLECULES, vol. 32, 1999, pages 5786 - 5792 |
See also references of EP4130097A4 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2022211100A1 (ja) * | 2021-04-01 | 2022-10-06 | 出光興産株式会社 | 樹脂、樹脂組成物、塗液組成物、フィルム、コーティング膜、電子写真感光体、絶縁材料、成形物、電子デバイス、および樹脂の製造方法 |
Also Published As
Publication number | Publication date |
---|---|
TW202146520A (zh) | 2021-12-16 |
JPWO2021201228A1 (ja) | 2021-10-07 |
EP4130097A1 (en) | 2023-02-08 |
KR20220164515A (ko) | 2022-12-13 |
EP4130097A4 (en) | 2024-04-17 |
CN115397886A (zh) | 2022-11-25 |
US20230340194A1 (en) | 2023-10-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
TWI471356B (zh) | Polycarbonate resin and an electrophotographic photoreceptor using the same | |
TWI570151B (zh) | Polycarbonate copolymer | |
JPH11172003A (ja) | 架橋ポリカーボネート樹脂の製造法および架橋ポリカーボネート樹脂ならびに電子写真感光体 | |
KR20110110149A (ko) | 폴리카보네이트 수지, 그것을 포함하는 도공액, 및 전자사진 감광체 | |
WO2013191174A1 (ja) | ポリカーボネート共重合体、それを用いた塗工液、および電子写真感光体 | |
WO2021201228A1 (ja) | 樹脂、樹脂前駆体組成物、塗液組成物、電子写真感光体、成形物、電子デバイス、および電子写真感光体の製造方法 | |
JP3637167B2 (ja) | 側鎖に架橋反応しうる官能基を有するポリカーボネート樹脂及びそれを用いた電子写真感光体 | |
JP6893205B2 (ja) | ポリカーボネート樹脂、ポリカーボネート樹脂の製造方法、塗工液、電子写真感光体、および電子写真装置 | |
JP5977762B2 (ja) | ポリカーボネート共重合体、並びにそれを用いた塗工液及び電子写真感光体 | |
JP3611654B2 (ja) | 電子写真感光体 | |
JP5680886B2 (ja) | ポリカーボネート共重合体、それを用いた塗工液、及び電子写真感光体 | |
WO2022211100A1 (ja) | 樹脂、樹脂組成物、塗液組成物、フィルム、コーティング膜、電子写真感光体、絶縁材料、成形物、電子デバイス、および樹脂の製造方法 | |
WO2021201227A1 (ja) | 樹脂、樹脂前駆体組成物、塗液組成物、電子写真感光体、電子写真感光体の製造方法、成形物および電子デバイス | |
JP2022159231A (ja) | 樹脂、樹脂組成物、塗液組成物、フィルム、コーティング膜、電子写真感光体、絶縁材料、成形物、電子デバイス、および樹脂の製造方法 | |
JP2022159223A (ja) | 樹脂、樹脂組成物、塗液組成物、フィルム、コーティング膜、電子写真感光体、絶縁材料、成形物、電子デバイス、および樹脂の製造方法 | |
JP3725258B2 (ja) | 電子写真感光体 | |
JP3618430B2 (ja) | 電子写真感光体 | |
JP3897444B2 (ja) | ポリカーボネート樹脂とその製造法および電子写真感光体 | |
WO2018116960A1 (ja) | ポリカーボネート共重合体、塗工液、電子写真感光体、電子写真装置、及びポリカーボネート共重合体の製造方法 | |
JP2001255674A (ja) | 電子写真感光体 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 21780035 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 2022512703 Country of ref document: JP Kind code of ref document: A |
|
ENP | Entry into the national phase |
Ref document number: 20227036081 Country of ref document: KR Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
ENP | Entry into the national phase |
Ref document number: 2021780035 Country of ref document: EP Effective date: 20221102 |