JP2010024345A - オルガノシロキサン共重合樹脂 - Google Patents
オルガノシロキサン共重合樹脂 Download PDFInfo
- Publication number
- JP2010024345A JP2010024345A JP2008187120A JP2008187120A JP2010024345A JP 2010024345 A JP2010024345 A JP 2010024345A JP 2008187120 A JP2008187120 A JP 2008187120A JP 2008187120 A JP2008187120 A JP 2008187120A JP 2010024345 A JP2010024345 A JP 2010024345A
- Authority
- JP
- Japan
- Prior art keywords
- bis
- hydroxyphenyl
- dicarboxylic acid
- organosiloxane
- resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000005375 organosiloxane group Chemical group 0.000 title claims abstract description 76
- 229920006026 co-polymeric resin Polymers 0.000 title claims description 51
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 33
- 125000003118 aryl group Chemical group 0.000 claims abstract description 20
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 15
- 125000001931 aliphatic group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001142 dicarboxylic acid group Chemical group 0.000 claims description 5
- 238000000465 moulding Methods 0.000 claims description 3
- 239000003205 fragrance Substances 0.000 claims 1
- 229920005989 resin Polymers 0.000 abstract description 45
- 239000011347 resin Substances 0.000 abstract description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 19
- 239000011342 resin composition Substances 0.000 abstract description 18
- 229920000728 polyester Polymers 0.000 abstract description 2
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 239000010408 film Substances 0.000 description 47
- 239000000243 solution Substances 0.000 description 32
- -1 siloxane structure Chemical group 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 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 18
- 239000002904 solvent Substances 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 235000010290 biphenyl Nutrition 0.000 description 12
- 239000004305 biphenyl Substances 0.000 description 12
- 125000006267 biphenyl group Chemical group 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 12
- 238000000576 coating method Methods 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 229920001230 polyarylate Polymers 0.000 description 10
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- 238000012695 Interfacial polymerization Methods 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 9
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- VOWWYDCFAISREI-UHFFFAOYSA-N Bisphenol AP Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=CC=C1 VOWWYDCFAISREI-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N Bisphenol F Natural products C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 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 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000002685 polymerization catalyst Substances 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- OWEYKIWAZBBXJK-UHFFFAOYSA-N 1,1-Dichloro-2,2-bis(4-hydroxyphenyl)ethylene Chemical compound C1=CC(O)=CC=C1C(=C(Cl)Cl)C1=CC=C(O)C=C1 OWEYKIWAZBBXJK-UHFFFAOYSA-N 0.000 description 3
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 3
- WVDRSXGPQWNUBN-UHFFFAOYSA-N 4-(4-carboxyphenoxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C=C1 WVDRSXGPQWNUBN-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IOEJYZSZYUROLN-UHFFFAOYSA-M Sodium diethyldithiocarbamate Chemical compound [Na+].CCN(CC)C([S-])=S IOEJYZSZYUROLN-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000035699 permeability Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- MQCPOLNSJCWPGT-UHFFFAOYSA-N 2,2'-Bisphenol F Chemical compound OC1=CC=CC=C1CC1=CC=CC=C1O MQCPOLNSJCWPGT-UHFFFAOYSA-N 0.000 description 2
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-Trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 2
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- DXCHWXWXYPEZKM-UHFFFAOYSA-N 2,4-ditert-butyl-6-[1-(3,5-ditert-butyl-2-hydroxyphenyl)ethyl]phenol Chemical compound C=1C(C(C)(C)C)=CC(C(C)(C)C)=C(O)C=1C(C)C1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1O DXCHWXWXYPEZKM-UHFFFAOYSA-N 0.000 description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- LVLNPXCISNPHLE-UHFFFAOYSA-N 2-[(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1CC1=CC=CC=C1O LVLNPXCISNPHLE-UHFFFAOYSA-N 0.000 description 2
- XBQRPFBBTWXIFI-UHFFFAOYSA-N 2-chloro-4-[2-(3-chloro-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=C(O)C(Cl)=CC=1C(C)(C)C1=CC=C(O)C(Cl)=C1 XBQRPFBBTWXIFI-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- CSOQDRZGMGKOGN-UHFFFAOYSA-N 2-tert-butyl-4-[1-(5-tert-butyl-4-hydroxy-2-methylphenyl)-2-methylpropyl]-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(C(C)C)C1=CC(C(C)(C)C)=C(O)C=C1C CSOQDRZGMGKOGN-UHFFFAOYSA-N 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 2
- URFNSYWAGGETFK-UHFFFAOYSA-N 4,4'-Dihydroxybibenzyl Chemical compound C1=CC(O)=CC=C1CCC1=CC=C(O)C=C1 URFNSYWAGGETFK-UHFFFAOYSA-N 0.000 description 2
- MIFGCULLADMRTF-UHFFFAOYSA-N 4-[(4-hydroxy-3-methylphenyl)methyl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(CC=2C=C(C)C(O)=CC=2)=C1 MIFGCULLADMRTF-UHFFFAOYSA-N 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 101001059734 Thermococcus litoralis (strain ATCC 51850 / DSM 5473 / JCM 8560 / NS-C) Trehalose/maltose-binding protein MalE Proteins 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000003373 anti-fouling effect Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 239000003990 capacitor Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000012788 optical film Substances 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- YCOZIPAWZNQLMR-UHFFFAOYSA-N pentadecane Chemical compound CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 1
- VBCBBRBVCPTOKP-UHFFFAOYSA-N 2,6-di(butan-2-yl)-4-[[3,5-di(butan-2-yl)-4-hydroxyphenyl]methyl]phenol Chemical compound CCC(C)C1=C(O)C(C(C)CC)=CC(CC=2C=C(C(O)=C(C(C)CC)C=2)C(C)CC)=C1 VBCBBRBVCPTOKP-UHFFFAOYSA-N 0.000 description 1
- WPZJSWWEEJJSIZ-UHFFFAOYSA-N 2,6-dibromo-4-[(3,5-dibromo-4-hydroxyphenyl)methyl]phenol Chemical compound C1=C(Br)C(O)=C(Br)C=C1CC1=CC(Br)=C(O)C(Br)=C1 WPZJSWWEEJJSIZ-UHFFFAOYSA-N 0.000 description 1
- JRWCWHILGVMUTD-UHFFFAOYSA-N 2,6-dibromo-4-[1-(3,5-dibromo-4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(Br)C(O)=C(Br)C=1)C1=CC(Br)=C(O)C(Br)=C1 JRWCWHILGVMUTD-UHFFFAOYSA-N 0.000 description 1
- HHWOEAFLIJITGC-UHFFFAOYSA-N 2,6-dichloro-4-[1-(3,5-dichloro-4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=C(Cl)C(O)=C(Cl)C=1)C1=CC(Cl)=C(O)C(Cl)=C1 HHWOEAFLIJITGC-UHFFFAOYSA-N 0.000 description 1
- ALLIENKNQNBVMR-UHFFFAOYSA-N 2,6-dimethyl-4-(3,3,5-trimethylcyclohexyl)phenol Chemical compound C1C(C)(C)CC(C)CC1C1=CC(C)=C(O)C(C)=C1 ALLIENKNQNBVMR-UHFFFAOYSA-N 0.000 description 1
- GSOYMOAPJZYXTB-UHFFFAOYSA-N 2,6-ditert-butyl-4-(3,5-ditert-butyl-4-hydroxyphenyl)phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 GSOYMOAPJZYXTB-UHFFFAOYSA-N 0.000 description 1
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- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- SJDACOMXKWHBOW-UHFFFAOYSA-N oxyphenisatine Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2NC1=O SJDACOMXKWHBOW-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Polyesters Or Polycarbonates (AREA)
Abstract
【解決手段】ポリオルガノシロキサンプロックを有するポリエステルであって、全ジカルボン酸に対し、50モル%以上の芳香族ジカルボン酸を含み、前記芳香族ジカルボン酸が、下記一般式(I)で示される芳香族ジカルボン酸であり、ポリオルガノシロキサンが樹脂中におけるオルガノシロキサン残基の割合が0.05質量%以上80質量%未満である。
【選択図】なし
Description
(2)ジカルボン酸が、芳香族ジカルボン酸/脂肪族ジカルボン酸=60/40〜100/0(モル比)であることを特徴とする(1)のオルガノシロキサン共重合樹脂。
(3)(1)または、(2)のオルガノシロキサン共重合樹脂を成形して得られる成型体、フィルム、コート被膜。
(樹脂組成)
日本電子製Lambda300WB NMRを用い1Hを測定核とし、測定周波数300MHzで測定を行った。
(分子量)
ウォーターズ社製GPCシステム(1515HPLCポンプおよび2414示差屈折計)、検出器として2410 RI、カラムとしてMixed-D(充填シリカゲル粒径5μm、チューブ長さ300x内径7.5mm)を用い、溶媒クロロホルムを流速1ml/分として、ポリスチレン換算で、重量平均分子量を測定した。
(Tg)
樹脂15mgをサンプルとし、DSC(示差走査熱量測定)装置(パーキンエルマー社製DSC7)を用いて、−80℃から300℃までを、昇温速度10℃/分の条件で測定を行い、得られた昇温曲線中のガラス転移に由来する2つの折曲点の温度の中間値を求め、これをガラス転移温度とした。
(溶解性)
樹脂10質量部に対してシクロヘキサノンまたはクロロホルム90質量部を加え、25℃において24時間攪拌し、ゲル物などの不溶物が発生せずに樹脂が溶解したかを判断した。両溶媒に溶解したものを○、クロロホルムのみに溶解したものを△、両溶媒ともに溶解なかったものを×とした。ここでは、環境負荷の低い塗工液の汎用溶媒であるシクロヘキサノンを用いた。
(溶液粘度)
N−メチルピロリドンを溶媒とし、樹脂固形分12%のポリマー溶液を作製し、25℃での溶液粘度を測定した。ここでは、測定時のポリマー溶液の濃度変化を抑制するため、揮発性の低いN−メチルピロリドンを用いた。
(カルボキシル価)
試験管に樹脂0.15gを精秤し、ベンジルアルコール5mlに加熱溶解した。クロロホルム10mlと前記の樹脂のベンジルアルコール溶液とを混合した後、フェノールレッドを指示薬として加え、撹拌しながら0.1N−KOHベンジルアルコール溶液で中和滴定を行なってカルボキシル価を求めた。
(アミン価)
樹脂0.5gをm−クレゾール20mlに60℃で溶解した後、室温まで冷却し、0.1N p−トルエンスルホン酸水溶液で滴定を行うことにより求めた。
上記で得られたオルガノシロキサン共重合樹脂に対して、樹脂15質量部にジクロロメタン85質量部を加えて作製した溶液を用い、PETフィルム上に溶液流延塗布を行い100μmの塗膜を作製した。得られた塗膜について、減圧にて120℃24時間乾燥して、樹脂フィルムを作製した。そして、以下の評価を行なった。ここでは、樹脂の溶解性に優れ、塗膜形成後に溶媒除去を行いやすい塩化メチレンを用いた。
(透過率)
日立製作所製U−4000形自記分光光度計を用い、得られた100μmの樹脂フィルムを、波長350nmおよび450nmにおける光線透過率を測定し 、透過率50%以上を合格とした。
(引張弾性率・引張伸度)
得られた100μmの樹脂フィルムで、インテスコ社 引張圧縮試験機を用い、JIS K-2318に準拠し、引張弾性率と、破断点での引張伸度を測定した。
(接触角)
得られた100μmの樹脂フィルムで、JIS R 3257に準拠し、協和界面科学社製接触角計CA−DT・A型を用いて、20℃×50%RHの環境下で、50μmの樹脂フィルムに対し、純水を滴下することで接触角の測定を行った。接触角が大きいほど、撥水性が高いことを示す。
(摩擦係数)
得られた100μmの樹脂フィルムで、協和界面科学製TS501を用い、SUS製の線状接触子を用いて、荷重50g、速度100m/秒で測定した。
攪拌装置を備えた反応容器中に、二価フェノール成分として2,2−ビス(4−ヒドロキシフェニル)プロパン19.57質量部(96.5モル部)、末端封止剤としてp−tert−ブチルフェノール(PTBP)0.40質量部(3.0モル部)、アルカリとして水酸化ナトリウム10.82質量部(300モル部)、重合触媒としてベンジル−トリ−n−ブチルアンモニウムクロライド(BTBAC)0.38質量部、ハイドロサルファイトナトリウム(SHS)0.16質量部を仕込み、水1000質量部に溶解した(水相)。また、これとは別に、塩化メチレン200質量部に、下記式(IV)で示すオルガノシロキサン9.94質量部(3.5モル部)を溶解した(有機相1)。この有機相1を、先に調製した水相中に強攪拌下で添加し、そのまま15℃で30分間攪拌した。
二価フェノール成分として2,2−ビス(3−メチル−4−ヒドロキシフェニル)プロパン(BisC)20.71質量部(96.3モル部)、末端封止剤としてp−tert−ブチルフェノール(PTBP)0.38質量部(3.0モル部)、アルカリとして水酸化ナトリウム10.21質量部(300モル部)、オルガノシロキサン9.92質量部(3.7モル部)、ジフェニルエーテル−4,4’−ジカルボン酸クロライド25.13質量部(101.5モル部)とした以外は、製造例1と同様に製造し、オルガノシロキサン共重合樹脂(P−2)を得た。その結果を表2に示す。得られたオルガノシロキサン共重合樹脂(P−2)の樹脂組成は、NMRで確認したところ、仕込みの配合通りの樹脂組成であった。
製造例1と同様にして、オルガノシロキサン共重合樹脂(P−3)〜(P−6)の製造を行った。その結果を表2に示す。得られたオルガノシロキサン共重合樹脂(P−3)〜(P−6)の樹脂組成は、NMRで確認したところ、すべて仕込みの配合通りの樹脂組成であった。
製造例1と同様にして、ポリアリレート樹脂(P−7)〜(P−9)の製造を行った。その結果を表2に示す。得られたポリアリレート樹脂(P−7)〜(P−9)の樹脂組成は、NMRで確認したところ、すべて仕込みの配合通りの樹脂組成であった。
製造例1と同様にして、オルガノシロキサン共重合樹脂(P−10)の製造を行った。その結果を表2に示す。得られたオルガノシロキサン共重合樹脂(P−10)の樹脂組成は、NMRで確認したところ、すべて仕込みの配合通りの樹脂組成であった。
製造例1と同様にして、オルガノシロキサン共重合樹脂(P−11)〜(P−20)の製造を行った。その結果を表3に示す。得られたオルガノシロキサン共重合樹脂(P−11)〜(P−20)の樹脂組成は、NMRで確認したところ、すべて仕込みの配合通りの樹脂組成であった。
製造例1で作成されたオルガノシロキサン共重合樹脂(P−1)15質量部にジクロロメタン85質量部を加えて作製した溶液を用い、PETフィルム上に溶液流延塗布を行い100μmの塗膜を作製した。得られた塗膜について、減圧にて120℃24時間乾燥して、樹脂フィルム(F−1)を作製し、各種評価を行なった。その結果を、表4に示す。
オルガノシロキサン共重合樹脂P−1の代わりにオルガノシロキサン共重合樹脂(P−2)を用いた以外は実施例1と同様にして、樹脂フィルム(F−2)を作製し、各種評価を行なった。評価結果を表4に示す。
実施例1と同様の操作を行って、樹脂フィルム(F−3)〜(F−6)の評価を行なった。評価結果を表4に示す。
実施例1と同様の操作を行って、樹脂フィルム(F−7)〜(F−10)の評価を行なった。評価結果を表4に示す。
実施例1と同様の操作を行って、樹脂フィルム(F−11)〜(F−14)の評価を行なった。評価結果を表5に示す。
実施例1と同様の操作を行って、樹脂フィルム(F−15)〜(F−20)の評価を行なった。評価結果を表5に示す。
Claims (3)
- (A)ジカルボン酸残基、(B)二価フェノール残基、および(C)オルガノシロキサン残基より構成されるオルガノシロキサン共重合樹脂であって、全ジカルボン酸に対し、60モル%以上の芳香族ジカルボン酸を含み、前記芳香族ジカルボン酸が、下記一般式(I)で示される芳香族ジカルボン酸であり、オルガノシロキサンが、下記一般式(II)で示されるオルガノシロキサンであり、樹脂中におけるオルガノシロキサン残基の割合が0.05質量%以上80質量%未満であることを特徴とするオルガノシロキサン共重合樹脂。
- ジカルボン酸が、芳香族ジカルボン酸/脂肪族ジカルボン酸=60/40〜100/0(モル比)であることを特徴とする請求項1に記載のオルガノシロキサン共重合樹脂。
- 請求項1または、2に記載のオルガノシロキサン共重合樹脂を成形して得られる成型体、フィルム、コート被膜。
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JP2012077128A (ja) * | 2010-09-30 | 2012-04-19 | Unitika Ltd | オルガノシロキサン共重合樹脂 |
JP2018185373A (ja) * | 2017-04-24 | 2018-11-22 | キヤノン株式会社 | 電子写真感光体、プロセスカートリッジ及び電子写真装置 |
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JPH09316185A (ja) * | 1996-05-29 | 1997-12-09 | M & S Kenkyu Kaihatsu Kk | ポリシロキサン変性ポリエステル樹脂の製造法 |
JP2000001530A (ja) * | 1998-06-16 | 2000-01-07 | Unitika Ltd | 被膜形成用樹脂及びその製造方法 |
JP2006290959A (ja) * | 2005-04-07 | 2006-10-26 | Unitika Ltd | 被膜形成用ポリエステル樹脂 |
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JPH09316185A (ja) * | 1996-05-29 | 1997-12-09 | M & S Kenkyu Kaihatsu Kk | ポリシロキサン変性ポリエステル樹脂の製造法 |
JP2000001530A (ja) * | 1998-06-16 | 2000-01-07 | Unitika Ltd | 被膜形成用樹脂及びその製造方法 |
JP2006290959A (ja) * | 2005-04-07 | 2006-10-26 | Unitika Ltd | 被膜形成用ポリエステル樹脂 |
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JP2012077128A (ja) * | 2010-09-30 | 2012-04-19 | Unitika Ltd | オルガノシロキサン共重合樹脂 |
JP2018185373A (ja) * | 2017-04-24 | 2018-11-22 | キヤノン株式会社 | 電子写真感光体、プロセスカートリッジ及び電子写真装置 |
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