JP5103252B2 - フッ素系共重合体溶液及びその製造方法 - Google Patents
フッ素系共重合体溶液及びその製造方法 Download PDFInfo
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- JP5103252B2 JP5103252B2 JP2008100267A JP2008100267A JP5103252B2 JP 5103252 B2 JP5103252 B2 JP 5103252B2 JP 2008100267 A JP2008100267 A JP 2008100267A JP 2008100267 A JP2008100267 A JP 2008100267A JP 5103252 B2 JP5103252 B2 JP 5103252B2
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- Prior art keywords
- fluorine
- meth
- acrylate monomer
- solution
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- 229910052731 fluorine Inorganic materials 0.000 title claims description 74
- 239000011737 fluorine Substances 0.000 title claims description 69
- 229920001577 copolymer Polymers 0.000 title claims description 68
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 67
- 239000000178 monomer Substances 0.000 claims description 49
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 42
- 239000002904 solvent Substances 0.000 claims description 41
- -1 alkyl vinyl ether Chemical compound 0.000 claims description 28
- 238000006116 polymerization reaction Methods 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000001153 fluoro group Chemical group F* 0.000 claims description 17
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 238000005227 gel permeation chromatography Methods 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 8
- IDBYQQQHBYGLEQ-UHFFFAOYSA-N 1,1,2,2,3,3,4-heptafluorocyclopentane Chemical compound FC1CC(F)(F)C(F)(F)C1(F)F IDBYQQQHBYGLEQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 5
- QVEJLBREDQLBKB-UHFFFAOYSA-N 1,1,2,2,3,3,4,5-octafluorocyclopentane Chemical compound FC1C(F)C(F)(F)C(F)(F)C1(F)F QVEJLBREDQLBKB-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 3
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 239000011248 coating agent Substances 0.000 description 38
- 239000003795 chemical substances by application Substances 0.000 description 31
- 238000000576 coating method Methods 0.000 description 31
- 239000000463 material Substances 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 18
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- 239000003999 initiator Substances 0.000 description 9
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- 230000000052 comparative effect Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000003973 paint Substances 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000007334 copolymerization reaction Methods 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 150000001451 organic peroxides Chemical class 0.000 description 6
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 5
- 229920001807 Urea-formaldehyde Polymers 0.000 description 5
- 239000003505 polymerization initiator Substances 0.000 description 5
- 230000002940 repellent Effects 0.000 description 5
- 239000005871 repellent Substances 0.000 description 5
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000004205 dimethyl polysiloxane Substances 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 4
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- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 4
- 239000005056 polyisocyanate Substances 0.000 description 4
- 229920001228 polyisocyanate Polymers 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000010894 electron beam technology Methods 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 239000010985 leather Substances 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- 150000007974 melamines Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- NWAHZAIDMVNENC-UHFFFAOYSA-N octahydro-1h-4,7-methanoinden-5-yl methacrylate Chemical compound C12CCCC2C2CC(OC(=O)C(=C)C)C1C2 NWAHZAIDMVNENC-UHFFFAOYSA-N 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- 230000000007 visual effect Effects 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- PAKCOSURAUIXFG-UHFFFAOYSA-N 3-prop-2-enoxypropane-1,2-diol Chemical compound OCC(O)COCC=C PAKCOSURAUIXFG-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
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- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
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- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
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- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 125000005641 methacryl group Chemical group 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
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- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
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- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
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- 238000010792 warming Methods 0.000 description 2
- NIONDZDPPYHYKY-SNAWJCMRSA-N (2E)-hexenoic acid Chemical compound CCC\C=C\C(O)=O NIONDZDPPYHYKY-SNAWJCMRSA-N 0.000 description 1
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- WLAYYZWRSCELHE-UHFFFAOYSA-N 1,1,2,2,3,3,4,4-octafluorocyclohexane Chemical compound FC1(F)CCC(F)(F)C(F)(F)C1(F)F WLAYYZWRSCELHE-UHFFFAOYSA-N 0.000 description 1
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- MITPAYPSRYWXNR-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluorocyclopentane Chemical compound FC1(F)CCC(F)(F)C1(F)F MITPAYPSRYWXNR-UHFFFAOYSA-N 0.000 description 1
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- UVMVIDWOUFITPW-UHFFFAOYSA-N 1,1,2,3,3-pentafluorocyclobutane Chemical compound FC1C(F)(F)CC1(F)F UVMVIDWOUFITPW-UHFFFAOYSA-N 0.000 description 1
- PQJGSPVYVGXTJW-UHFFFAOYSA-N 1,2,3,4,5,6-hexafluorocyclohexane Chemical compound FC1C(F)C(F)C(F)C(F)C1F PQJGSPVYVGXTJW-UHFFFAOYSA-N 0.000 description 1
- UBWKESXQKRAGIX-UHFFFAOYSA-N 1,2,3,4,5-pentafluorocyclopentane Chemical compound FC1C(F)C(F)C(F)C1F UBWKESXQKRAGIX-UHFFFAOYSA-N 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- SKYXLDSRLNRAPS-UHFFFAOYSA-N 1,2,4-trifluoro-5-methoxybenzene Chemical compound COC1=CC(F)=C(F)C=C1F SKYXLDSRLNRAPS-UHFFFAOYSA-N 0.000 description 1
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- KOGAQDUWOGTLRE-UHFFFAOYSA-N 2-(ethenoxymethoxymethyl)oxirane Chemical compound C=COCOCC1CO1 KOGAQDUWOGTLRE-UHFFFAOYSA-N 0.000 description 1
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- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
Description
CH2=CHCOOCH2CH2(CF2)4F、CH2=CHCOOCH2CH2(CF2)6F、CH2=CHCOOCH2CH2(CF2)8F、CH2=CHCOOCH2CH2(CF2)10F、CH2=CHCOOCH2CH2(CF2)12F、CH2=CHCOOCH2CH2(CF2)20F、CH2=C(CH3)COOCH2CH2(CF2)4F、CH2=C(CH3)COOCH2CH2(CF2)6F、CH2=C(CH3)COOCH2CH2(CF2)8F、CH2=C(CH3)COOCH2CH2(CF2)10F、CH2=C(CH3)COOCH2CH2(CF2)12F、CH2=C(CH3)COOCH2CH2(CF2)20F、CH2=CHCOOCH2CF3、CH2=CHCOOCH2C2F5、CH2=CHCOOCH2(CF2)8F、CH2=CHCOOCH2(CF2)20F、CH2=C(CH3)COOCH2CF3、CH2=C(CH3)COOCH2(CF2)8F、CH2=C(CH3)COOCH2(CF2)20F、CH2=C(CH3)COOCH2CF(CF3)2、CH2=C(CH3)COOCH2CFHCF3、CH2=C(CH3)COO(CH2)6(CF2)10F、CH2=C(CH3)COO(CH2)6CF(CF3)2、CH2=C(CH3)COOCH(CH3)CF2CFHCF3、CH2=C(CH3)COOCH(C2H5)C10F21、CH2=CHCOOCH(CF3)C8F17、CH2=CFCOOCH2(CF2)2F、CH2=CFCOOCH2CH2(CF2)6F、CH2=CH(CF2)6F、CH2=CH(CF2)8F、CH2=CH(CF2)10F、CH2=CH(CF2)12F、CH2=CHCOOCH2(CF2)2H、CH2=CHCOOCH2(CF2)4H、CH2=CHCOOCH2(CF2)6H、CH2=CHCOOCH2(CF2)8H、CH2=CHCOOCH2(CF2)10H、CH2=CHCOOCH2(CF2)12H、CH2=CHCOOCH2(CF2)14H、CH2=CHCOOCH2(CF2)18H、CH2=CHCOOCH2(CF2)20H、CH2=C(CH3)COOCH2(CF2)4H、CH2=C(CH3)COOCH2(CF2)6H、CH2=C(CH3)COOCH2(CF2)8H、CH2=CHCOOC(CH3)2C4F8H、CH2=C(CH3)COOC(CH3)2C4F8H、CH2=CHCOOC(CH3)2C6F12H、CH2=C(CH3)COOC(CH3)2C6F12H、CH2=CHCOOCH2CH(OH)CH2C8F17、CH2=C(CH3)COOCH2CH(OH)C4H8C18F37、CH2=CHCOO(CH2)8N(CH3)COC12F25、CH2=CHCOO(CH2)2N(C2H5)SO2C8F17
等が挙げられる。更に、主鎖中に酸素原子が介在するモノマー(例えば(CF3)2OFOCF2CF2−等)であっても良い。特に、CH2=CHCOOCH2CH2(CF2)8F(2−ペルフルオロオクチルエチルアクリレート)、CH2=C(CH3)COOCH2CH2(CF2)8F(2−ペルフルオロオクチルエチルメタクリレート)、CH2=C(CH3)COOCH2CH2(CF2)4F、CH2=C(CH3)COOCH2CH2(CF2)6Fが好ましい。これらのフッ素化アルキル基含有単量体は、それぞれ単独で用いてもよいし、2種以上を組み合せてもよい。
内容積540ccのステンレス製攪拌機付きオートクレーブ(耐圧10MPa)に、1,1,2,2,3,3,4−ヘプタフルオロシクロペンタン(以下、c−HFPと略す)360g、メチルメタクリレート(以下、MMAと略す)9.2g(50モル%)、ジシクロペンタニルメタクリレート2.0g(5モル%)、2−(ペルフルオロオクチル)エチルメタクリレート37.9g(40モル%)、t−ブチルパーオキシピバレート(触媒)0.64gを入れた。系内の酸素を除去する為に窒素置換を2回行い、更に深冷脱気した後、テトラフルオロエチレン(以下、TFEと略す)1g(5モル%)を入れ、常温に戻した。続いて、攪拌しながら内温を60℃に昇温した。その後、攪拌しながら加温し60℃一定を保持して反応を17時間継続した。17時間後、攪拌を停止し、オートクレーブを水冷した。オートクレーブより取り出された反応液は、無色透明液体(目視による外観観察並びに濁度計観測を実施)であり、ゲル化を生じることはなかった。得られたフッ素系共重合体溶液の収量は407g、加熱残分(100℃で24時間乾燥操作前後の重量変化から算出)は11.6%、反応率は94%であった。又、フッ素系共重合体溶液中に溶解している含フッ素共重合体の燃焼法によるフッ素含有量は51重量%、GPC(東ソー(株)高速GPC装置HLC−8220GPC、THF溶媒、ポリスチレン換算)で測定した重量平均分子量(Mw)は81000であった。
日本電色工業(株)製 濁度計(濁り計)NDH2000により、作成塗膜の光線透過率を、常温にて測定し、次式によって算出した。
ヘイズ値(%)=(散乱光/全光線透過光)×100
[表面性]
目視により5段階評価を行った。
良好(表面性状が平滑である)
やや良好(表面性状がおおよそ平滑である)
普通(平滑の部分と凹凸の部分がある)
やや劣る(凹凸の部分がかなり目立つ)
劣る(表面性状が平滑でなく、凹凸である)
[撥水性]
協和界面科学(株)製 CONTACT-ANGLE METER CA-DTにて、各塗膜表面と純水との接触角を常温にて測定した。
[撥油性]
協和界面科学(株)製 CONTACT-ANGLE METER CA-DTにて、各塗膜表面とn−デカンとの接触角を常温にて測定した。
[鉛筆硬度]
JIS−K5400 6.14(鉛筆引っかき試験)により常温にて試験した。
[屈折率(nD)]
(株)アタゴ製 多波長アッベ屈折計DR-M2 干渉フィルター589(D)nmを使用して測定した。
測定温度23℃ 波長589nm(D線)
[静摩擦係数]
新東科学(株)ポータブル摩擦計 HEIDONトライボギアミューズ TYPE:94iにて
各塗膜表面とナイロン繊維との静摩擦係数を常温にて測定した。
表1〜2に示す仕込み組成にて、実施例1と同様に反応を行い、フッ素系共重合体溶液を得た。又、実施例1と同様に評価用塗膜を作成し、実施例1と同様に評価を行った。その結果を表1〜2に示す。
表3に示すように、実施例1の仕込み組成のうち、重合溶媒を酢酸ブチル400gに変えた以外は実施例1と同様な仕込組成及び反応条件にて反応を行った。その結果、溶液では得られずゲル化物となった。
表3に示すように、重合溶媒に比較例2ではハイドロフルオロエーテル(HFE)であるNovecTMHFE−7200(C4F9OC2H5:住友スリーエム(株)製)を用い、又比較例3では直鎖HFCであるバートレル−XF(HFC-43-10mee)(CF3CHFCHFCF2CF3:三井・デュポンフロロケミカル(株)製、バートレルは登録商標)を用い、表3に示す仕込組成にて実施例1と同様な反応条件にて反応を行った。その結果、溶液では得られなかった。
表4に示すように、実施例1の各仕込みモノマー量を4倍量(重量比)とし、触媒を0.64gから0.01gに減量し、重合溶媒を360gから200gに減量し、また反応温度を17時間から48時間に延長した以外は実施例1と同様な仕込組成で反応を行った。その結果、オートクレーブより取り出された反応液は、不透明な不均一液体(目視による外観観察並びに濁度計観測を実施)であり、実施例1のように無色透明液体は得られなかった。
表4に示すように、実施例1の各仕込みモノマー量を1/5量(重量比)とし、触媒を0.64gから1.27gに増量した以外は実施例1と同様な仕込組成及び反応条件で反応を行った。その結果、オートクレーブより取り出された反応液は、無色透明液体(目視による外観観察並びに濁度計観測を実施)であった。しかしながら、実施例1と同様にして得られたフッ素系共重合体溶液を、ガラス板上に#16バーコーターにて塗布し、常温で4日間乾燥し、評価用塗膜を作成したところ、塗膜表面にハジキが発生し、表面性状が平滑な塗膜は得られなかった。
MMA:メチルメタクリレート
c−HFP:1,1,2,2,3,3,4−ヘプタフルオロシクロペンタン
c−OFP:1H,2H−オクタフルオロシクロペンタン
M%:モル%
Claims (11)
- フルオロオレフィンとフッ素化アルキル基含有(メタ)アクリレート単量体とを必須の重合成分として含み、GPC(ゲル パーミッション クロマトグラフィー)で測定される重量平均分子量値(Mw)が、5,000〜3,000,000である含フッ素共重合体が、水素原子とフッ素原子と炭素原子のみから構成される環状フッ素系溶剤に溶解されてなることを特徴とするフッ素系共重合体溶液。
- 含フッ素共重合体が、(1)フルオロオレフィンの5〜30モル%、及び(2)フッ素化アルキル基含有(メタ)アクリレート単量体の10〜80モル%、を含み構成されることを特徴とする請求項1記載のフッ素系共重合体溶液。
- フルオロオレフィンとフッ素化アルキル基含有(メタ)アクリレート単量体、さらに、ジシクロペンタニル基含有(メタ)アクリレート単量体及びジシクロペンテニル基含有(メタ)アクリレート単量体より選択される少なくとも1種の単量体を必須の重合成分として含み、GPC(ゲル パーミッション クロマトグラフィー)で測定される重量平均分子量値(Mw)が、5,000〜3,000,000である含フッ素共重合体が、水素原子とフッ素原子と炭素原子のみから構成される環状フッ素系溶剤に溶解されてなることを特徴とするフッ素系共重合体溶液。
- 含フッ素共重合体が、(1)フルオロオレフィンの5〜30モル%、(2)フッ素化アルキル基含有(メタ)アクリレート単量体の10〜80モル%、ならびに(3)ジシクロペンタニル基含有(メタ)アクリレート単量体及びジシクロペンテニル基含有(メタ)アクリレート単量体より選択される少なくとも1種の単量体の1〜25モル%、を含み構成されることを特徴とする請求項3記載のフッ素系共重合体溶液。
- 水素原子とフッ素原子と炭素原子のみから構成される環状フッ素系溶剤を溶媒に、フッ素化アルキル基含有(メタ)アクリレート単量体を含む重合成分を溶解し、30〜110℃の温度条件において、その溶液を攪拌しながら溶液中にフルオロオレフィンを導入し、フルオロオレフィンとフッ素化アルキル基含有(メタ)アクリレート単量体とを必須の重合成分として含む共重合体を合成する、ことを特徴とする請求項1又は2に記載のフッ素系共重合体溶液の製造方法。
- 水素原子とフッ素原子と炭素原子のみから構成される環状フッ素系溶剤を溶媒に、ジシクロペンタニル基含有(メタ)アクリレート単量体及びジシクロペンテニル基含有(メタ)アクリレート単量体より選択される少なくとも1種の単量体と、フッ素化アルキル基含有(メタ)アクリレート単量体とを含む重合成分を溶解し、30〜110℃の温度条件において、その溶液を攪拌しながら溶液中にフルオロオレフィンを導入し、フルオロオレフィンとフッ素化アルキル基含有(メタ)アクリレート単量体、さらに、ジシクロペンタニル基含有(メタ)アクリレート単量体及びジシクロペンテニル基含有(メタ)アクリレート単量体より選択される少なくとも1種の単量体を必須の重合成分として含む共重合体を合成する、ことを特徴とする請求項3又は4に記載のフッ素系共重合体溶液の製造方法。
- 溶液が無色透明であることを特徴とする請求項1〜4のいずれか1項に記載のフッ素系共重合体溶液。
- 含フッ素共重合体が、水酸基含有不飽和単量体、アルキルビニルエーテル、アルキルアリルエーテル、フッ素化ビニルエーテル、メタクリル酸エステル、アクリル酸エステル及び不飽和カルボン酸の内から選択される少なくとも1種の重合成分を、さらに含むことを特徴とする請求項1〜4のいずれか1項に記載のフッ素系共重合体溶液。
- フルオロオレフィンが、CF2=CXY(式中、X、Yはそれぞれ水素原子、フッ素原子、塩素原子、またはトリフルオロメチル基を示し、同一であっても異なっていても良い)で表されるものであることを特徴とする請求項1〜4のいずれか1項に記載のフッ素系共重合体溶液。
- 水素原子とフッ素原子と炭素原子のみから構成される環状フッ素系溶剤が、1,1,2,2,3,3,4−ヘプタフルオロシクロペンタン、1H,2H−オクタフルオロシクロペンタンの内から選択される少なくとも1種であることを特徴とする請求項1〜4のいずれか1項に記載のフッ素系共重合体溶液。
- フッ素化アルキル基含有(メタ)アクリレート単量体が、CH2=CHCOOCH2CH2、(CF2)8F、CH2=C(CH3)COOCH2CH2(CF2)8F、CH2=C(CH3)COOCH2CH2(CF2)4F、CH2=C(CH3)COOCH2CH2(CF2)6Fの内から選択される少なくとも1種であることを特徴とする請求項1〜4のいずれか1項に記載のフッ素系共重合体溶液。
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