JP5038129B2 - アクリレート基を含有するパーフルオロポリエーテル - Google Patents
アクリレート基を含有するパーフルオロポリエーテル Download PDFInfo
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- JP5038129B2 JP5038129B2 JP2007511359A JP2007511359A JP5038129B2 JP 5038129 B2 JP5038129 B2 JP 5038129B2 JP 2007511359 A JP2007511359 A JP 2007511359A JP 2007511359 A JP2007511359 A JP 2007511359A JP 5038129 B2 JP5038129 B2 JP 5038129B2
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- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title description 47
- 239000010702 perfluoropolyether Substances 0.000 title description 2
- 229920000570 polyether Polymers 0.000 claims abstract description 36
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 239000002131 composite material Substances 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims description 49
- -1 acryl group Chemical group 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 22
- 239000000758 substrate Substances 0.000 claims description 22
- 125000002947 alkylene group Chemical group 0.000 claims description 20
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 15
- 125000000962 organic group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 230000003373 anti-fouling effect Effects 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 33
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- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 17
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
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- 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 7
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- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical compound C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 4
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- PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 230000004927 fusion Effects 0.000 description 3
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 3
- 125000005395 methacrylic acid group Chemical group 0.000 description 3
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 230000000269 nucleophilic effect Effects 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 description 2
- PCLLJCFJFOBGDE-UHFFFAOYSA-N (5-bromo-2-chlorophenyl)methanamine Chemical compound NCC1=CC(Br)=CC=C1Cl PCLLJCFJFOBGDE-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 2
- PASIEQDVKZQWRI-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol 3-hydroxy-2,2-dimethylpropanoic acid prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.OCC(C)(C)CO.OCC(C)(C)C(O)=O PASIEQDVKZQWRI-UHFFFAOYSA-N 0.000 description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 2
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 2
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 150000001412 amines Chemical class 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
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 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 2
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- 229910021641 deionized water Inorganic materials 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
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- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 150000003512 tertiary amines Chemical class 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- OZGWOALFBHODRB-UHFFFAOYSA-N (1,2,2,3,3,4,4,5,5,6,6-undecafluorocyclohexyl)methyl prop-2-enoate Chemical compound FC1(F)C(F)(F)C(F)(F)C(F)(COC(=O)C=C)C(F)(F)C1(F)F OZGWOALFBHODRB-UHFFFAOYSA-N 0.000 description 1
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- WEERVPDNCOGWJF-UHFFFAOYSA-N 1,4-bis(ethenyl)benzene Chemical compound C=CC1=CC=C(C=C)C=C1 WEERVPDNCOGWJF-UHFFFAOYSA-N 0.000 description 1
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
- GJFNRSDCSTVPCJ-UHFFFAOYSA-N 1,8-bis(dimethylamino)naphthalene Chemical compound C1=CC(N(C)C)=C2C(N(C)C)=CC=CC2=C1 GJFNRSDCSTVPCJ-UHFFFAOYSA-N 0.000 description 1
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- DLEWDCPFCNLJEY-UHFFFAOYSA-N 1-morpholin-4-ylpropan-1-one Chemical compound CCC(=O)N1CCOCC1 DLEWDCPFCNLJEY-UHFFFAOYSA-N 0.000 description 1
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 description 1
- DSCFFEYYQKSRSV-UHFFFAOYSA-N 1L-O1-methyl-muco-inositol Natural products COC1C(O)C(O)C(O)C(O)C1O DSCFFEYYQKSRSV-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
- IEORSVTYLWZQJQ-UHFFFAOYSA-N 2-(2-nonylphenoxy)ethanol Chemical compound CCCCCCCCCC1=CC=CC=C1OCCO IEORSVTYLWZQJQ-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
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- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- YIJYFLXQHDOQGW-UHFFFAOYSA-N 2-[2,4,6-trioxo-3,5-bis(2-prop-2-enoyloxyethyl)-1,3,5-triazinan-1-yl]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCN1C(=O)N(CCOC(=O)C=C)C(=O)N(CCOC(=O)C=C)C1=O YIJYFLXQHDOQGW-UHFFFAOYSA-N 0.000 description 1
- DZZAHLOABNWIFA-UHFFFAOYSA-N 2-butoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCC)C(=O)C1=CC=CC=C1 DZZAHLOABNWIFA-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- XNFIEYMGNIUQIF-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.CCC(CO)(CO)CO XNFIEYMGNIUQIF-UHFFFAOYSA-N 0.000 description 1
- ZACVGCNKGYYQHA-UHFFFAOYSA-N 2-ethylhexoxycarbonyloxy 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC(=O)OOC(=O)OCC(CC)CCCC ZACVGCNKGYYQHA-UHFFFAOYSA-N 0.000 description 1
- CKKQLOUBFINSIB-UHFFFAOYSA-N 2-hydroxy-1,2,2-triphenylethanone Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C(=O)C1=CC=CC=C1 CKKQLOUBFINSIB-UHFFFAOYSA-N 0.000 description 1
- YOJAHTBCSGPSOR-UHFFFAOYSA-N 2-hydroxy-1,2,3-triphenylpropan-1-one Chemical compound C=1C=CC=CC=1C(=O)C(C=1C=CC=CC=1)(O)CC1=CC=CC=C1 YOJAHTBCSGPSOR-UHFFFAOYSA-N 0.000 description 1
- RZCDMINQJLGWEP-UHFFFAOYSA-N 2-hydroxy-1,2-diphenylpent-4-en-1-one Chemical compound C=1C=CC=CC=1C(CC=C)(O)C(=O)C1=CC=CC=C1 RZCDMINQJLGWEP-UHFFFAOYSA-N 0.000 description 1
- DIVXVZXROTWKIH-UHFFFAOYSA-N 2-hydroxy-1,2-diphenylpropan-1-one Chemical compound C=1C=CC=CC=1C(O)(C)C(=O)C1=CC=CC=C1 DIVXVZXROTWKIH-UHFFFAOYSA-N 0.000 description 1
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- 125000004079 stearyl 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])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
- 239000004575 stone Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003608 titanium Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 125000005289 uranyl group Chemical group 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/22—Esters containing halogen
- C08F220/24—Esters containing halogen containing perhaloalkyl radicals
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/323—Polymers modified by chemical after-treatment with inorganic compounds containing halogens
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
- C08G65/223—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens
- C08G65/226—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens containing fluorine
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- C—CHEMISTRY; METALLURGY
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
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Description
(F(RfO)xQZ1R1NR2CH2CH2C(=O)Z2)yM(Z3C(=O)CR3=CH2)z
又は
X[((RfO)xQZ1R1NR2CH2CH2C(=O)Z2)yM(Z3C(=O)CR3=CH2)z]b
(式中、
各Rfは、独立して、1〜6個の炭素原子を有するフッ素化アルキレン基を表し、
各xは、独立して、2以上の整数を表し、
各Qは、独立して、−CF2−、−CF(CF3)−、−CF2CF2−、−CF2CF2CF2−、−CF2CF(CF3)−、−CF(CF3)CF2−、−CF2CF2CH2−、−CF2CH2−、−CF2CF2C(=O)−、−CF2C(=O)−、−CF(CF3)C(=O)−、−CF(CF3)CH2−、1〜6個の炭素原子を有するアルキレン基、又は1〜6個の炭素原子を有するヘテロアルキレン基を表し、
各Z1、Z2およびZ3は、独立して、−S−、−O−、−NH−、又は−NR2−を表し、
各R1は、独立して、アルキレン基、アラルキレン基、又はヘテロアルキレン基を表し、
各R2は、独立して、H、1〜6個の炭素原子を有するアルキル基、−CH2CH2C(=O)Z2M(Z3C(=O)CR3=CH2)z、又は−R1Z1Q(ORf)xFを表し、
各R3は、独立して、H、F、又はメチルを表し、
各yおよびzは、独立して、1以上の整数を表し、
各Mは、y+z価の多価有機基を表し、
Xは、b価の多価有機基を表し、
bは、2以上の整数を表す)
で示される少なくとも1種類の化合物を含む、重合性組成物に関する。
反応性フッ素化ポリエーテル、および
ポリ(メタ)アクリル化合物
を、そのマイケル型付加物を形成するのに十分な条件で混合することを含む、重合性組成物の製造方法を提供し、ここで、重合性化合物は少なくとも1つのアクリル基を有する。
(F(RfO)xQZ1R1NR2CH2CH2C(=O)Z2)yM(Z3C(=O)CR3=CH2)z
又は
X[((RfO)xQZ1R1NR2CH2CH2C(=O)Z2)yM(Z3C(=O)CR3=CH2)z]b
(式中、
各Rfは、独立して、1〜6個の炭素原子を有するフッ素化アルキレン基を表し、
各xは、独立して、2以上の整数を表し、
各Qは、独立して、−CF2−、−CF(CF3)−、−CF2CF2−、−CF2CF2CF2−、−CF2CF(CF3)−、−CF(CF3)CF2−、−CF2CF2CH2−、−CF2CH2−、−CF2CF2C(=O)−、−CF2C(=O)−、−CF(CF3)C(=O)−、−CF(CF3)CH2−、1〜6個の炭素原子を有するアルキレン基、又は1〜6個の炭素原子を有するヘテロアルキレン基を表し、
各Z1、Z2およびZ3は、独立して、−S−、−O−、−NH−、−NR2−を表し、
各R1は、独立して、アルキレン基、アラルキレン基、又はヘテロアルキレン基を表し、
各R2は、独立して、H、1〜6個の炭素原子を有するアルキル基、−CH2CH2C(=O)Z2M(Z3C(=O)CR3=CH2)z、又は−R1Z1Q(ORf)xFを表し、
各R3は、独立して、H、F、又はメチルを表し、
各yおよびzは、独立して、1以上の整数を表し、
各Mは、y+z価の多価有機基を表し、
Xは、b価の多価有機基を表し、
bは、2以上の整数を表す)
で記載される少なくとも1種類の化合物を含む重合性組成物を少なくとも部分的に重合させることによって調製可能な防汚組成物を基材上に有する基材を備える複合物品を提供する。
(F(RfO)xQZ1R1NR2CH2CH2C(=O)Z2)yM(Z3C(=O)CR3=CH2)z
又は
X[((RfO)xQZ1R1NR2CH2CH2C(=O)Z2)yM(Z3C(=O)CR3=CH2)z]b
−CH2CH2OCH2CH2OCH2CH2−、−CH2NHCH2CH2CH2NHCH2−、−CH2CH2NHCH2CH2NHCH2CH2−、−CH2CH2NHCH2CH2N(CH2CH3)CH2CH2−、−CH2CH2CH2−、−CH2CH2−および−CH2−。
F(RfO)xQZ1R1NR2H
又は
X(RfO)xQZ1R1NR2H
式中、Rf、x、Q、Z1、R1、R2およびXは、前記に定義される通りである。
FC−1 F(CF(CF3)CF2O) aCF(CF3)C(=O)OCH3、式中、
aは平均約6.3、平均分子量は1,211g/molであり、米国特許
第3,250,808号明細書(ムーア(Moore)ら)に報告されて
いる方法に従って調製することができ、分留により精製する。
FC−2 次式、CH3O2C(OCF2CF2)p[OCF2CF(CF3)]q(OCF
2)rCO2CH3を有すると考えられ、平均分子量約2,000g/mol
、ニュージャージー州ソロフェア、オージモント,USA(Ausimo
nt, USA, Thorofare, New Jersey)から
「フォンブリンZ−ディール(FOMBLIN Z−DEAL)」の商品
名で入手可能。
FC−3 F(CF(CF3)CF2O)aCF(CF3)C(=O)F、式中、aは平
均約5.7、平均分子量は1,115g/molであり、米国特許第3,
250,808号明細書(ムーア(Moore)ら)に報告されている方
法に従って調製することができ、分留により精製する。
FC−4 F(CF(CF3)CF2O)aCF(CF3)C(=O)NHCH2CH2O
C(=O)CH=CH2を以下のように調製した:
オリゴマーヘキサフルオロプロピレンオキシドメチルエステルFC−1
を50.0g、200mLの丸底フラスコに入れた。そのフラスコを窒素
パージし、水浴に入れ、温度を50℃以下に維持した。このフラスコに2
−アミノエタノール3.0g(0.045mol)を加えた。反応混合物
を約1時間攪拌した後、反応混合物の赤外スペクトルは、1790cm-1
のメチルエステルバンドの完全な消失と1710cm-1の強いアミドカル
ボニル伸縮の存在を示した。メチルt−ブチルエーテル(200mL)を
反応混合物に加え、有機相を5重量%のHCl水で2回洗浄し、未反応の
アミンとメタノールを除去した。有機相の層を合わせて、無水MgSO4
で乾燥させた。メチルt−ブチルエーテルを減圧下で(まずアスピレータ
を使用し、次いで0.1mmHgの真空を使用して)除去し、HFPOC
(=O)NHCH2CH2OHを透明で粘稠な液体として得た。
オーバーヘッドスターラーを装備した3つ口丸底フラスコに、HFPO
C(=O)NHCH2CH2OH200g(0.1468mol)、トリエ
チルアミン18.07g(0.1786mol)、4−メトキシルフェノ
ール8mg、および酢酸エチル200gを投入した。次に、室温で、塩化
アクリロイル16.16g(0.1786mol)をフラスコに30分に
わたって加えた。反応物を約2.75時間攪拌した後、1重量%の硫酸水
、1重量%の重炭酸ナトリウム水、および水で連続的に洗浄した。得られ
た生成物を、ドイツ、ダルムシュタット、EMサイエンス(EM Sci
ence, Darmstadt, Germany)から「SX014
3U−3」の商品名で入手したシリカゲル(グレード62、60〜200
メッシュ)のクロマトグラフィーで、溶離液として(容積で)35/65
の酢酸エチル/ヘプタンを使用して精製した。
FC−5 ω−ヒドロ−2,2,3,3,4,4,5,5−オクタフルオロペンチル
アクリレート(H−C4F8−CH2OC(=O)CH=CH2)は、サウス
カロライナ州ウエストコロンビア、オークウッド・プロダクツ(Oakw
ood Products, West Columbia, Sout
h Carolina)から入手した。
AM−1 N−メチル−1,3−プロパンジアミン
AM−2 N−エチル−1,2−エタンジアミン
AM−3 2−(2−アミノエチルアミノ)エタノール
AM−4 ペンタエチレンヘキサアミン
AM−5 エチレンジアミン
AM−6 N−メチルエタノールアミン
AM−7 1,3−プロパンジアミン
AC−1 トリメチロールプロパントリアクリレート、ペンシルバニア州エクストン
、サートマー社(Sartomer Company, Exton,
Pennsylvania)から「SR351」の商品名で入手、公称分
子量=296g/mol。
AC−2 ペンタエリトリトールトリアクリレート、サートマー社(Sartome
r Company)から「SR444」の商品名で入手、公称分子量=
298g/mol。
AC−3 ジペンタエリトリトールペンタアクリレート、サートマー社(Sarto
mer Company)から「SR399LV」の商品名で入手、公称
分子量=508g/mol。
AC−4 エトキシ化(3)トリメチロールプロパントリアクリレート、サートマー
社(Sartomer Company)から「SR454」の商品名で
入手、公称分子量=428g/mol。
AC−5 エトキシ化(4)ペンタエリトリトールテトラアクリレート、サートマー
社(Sartomer Company)から「SR494」の商品名で
入手、公称分子量=526g/mol。
AC−6 1,4−ブタンジオールジアクリレート、サートマー社(Sartome
r Company)から「SR213」の商品名で入手、公称分子量=
198g/mol。
PI−1 光開始剤、2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オ
ン、ニューヨーク州タリータウン、チバ・スペシャルティ・ケミカルズ社
(Ciba Specialty Chemicals, Corpor
ation, Tarrytown, New York)から「ダロキ
ュア(DAROCUR)1173」の商品名で入手可能。
PI−2 光開始剤、ベンジルジメチルケタール、サートマー社(Sartomer
Company)から「エサキュア(ESACURE) KB−1」の
商品名で入手。
FS C4F9OCH3、3M社(3M Company)から「3Mノベック工
学流体HFE−7100(3M NOVEC ENGINEERED F
LUID HFE−7100)」の商品名で入手可能。
HFPO− F(CF(CF3)CF2O)aCF(CF3)−、式中、aは約6.3であ
る。
S1 透明ポリエチレンテレフタレートフィルム、デラウェア州ウィルミントン
、イー・アイ・デュポン・ドゥ・ヌムール・アンド・カンパニー(E.I
.du Pont de Nemours and Company,
Wilmington,Delaware)から「メリネックス(MEL
INEX) 618」の商品名で入手、厚さが5.0ミル(0.1mm)
でプライマー処理された面を有する。米国特許第6,299,799号明
細書(クレイグ(Craig)ら)の実施例3に記載のものと実質的に同
じであったハードコート組成物を、プライマー処理された面にコーティン
グし、硬化させた(公称硬化膜厚は5マイクロメートルであった)。
S2 ジョージア州シーダータウン、U.S.A.キモト・テック(U.S.A
.Kimoto Tech, Cedartown, Georgia)
から「N4D2A」の商品名で入手可能なハードコート表面層を有する艶
消しフィルム。
チーズクロスを35cm/秒の速度で揺動させることができる機械装置内に、試験される試料(S1基材:30.5cm×22.9cm;S2基材:30.5cm×15.2cm;)を取り付け、チーズクロスを12層に折り畳んでゴムガスケットでスタイラスに固定する。チーズクロスが、試料のコーティング方向に直交する方向に移動するように、試料を取り付ける。スタイラスは、平坦で円筒状の幾何学的形状を有し、直径1.25インチ(3.2cm)であった。装置は、フィルム表面に垂直なスタイラスによって及ぼされる力が増加するように様々な重りが取り付けられるプラットホームを装備した。チーズクロスは、ペンシルバニア州ハッツフィールド、EMSアクイジション社(EMS Acquisition Corp., Hatsfield, Pennsylvania)の事業部の一部門である、EMSパッケージング、サマーズ・オプティカル(Summers Optical, EMS Packaging)から「ミル・スペックCCC−C−440製品番号S12905(MIL SPEC CCC−C−440 PRODUCT#S12905)」の商品名で入手した。「清拭」は、1回の10cmの移動と定義される。各試料について、スタイラスに加えたグラム単位の重量と、試験条件のために使用した清拭の数を報告する。
おおよその寸法が2.5cm×4cmの塗工フィルムのサンプルをカットし、両面粘着接着テープを使用して、標準的な顕微鏡スライドグラスに取り付ける。受け取った状態の試薬用ヘキサデカン(ウィスコンシン州ミルウォーキー、アルドリッチ・ケミカル社(Aldrich Chemical Company, Milwaukee, Wisconsin))、および、ミリポア社(マサチューセッツ州ビレリカ)(Millipore Corporation(Billerica, Massachusetts))から入手可能な濾過システム「ミリQ(MIILI−Q)」で濾過された脱イオン水、および、ASTプロダクツ(マサチューセッツ州ビレリカ)(AST Products(Billerica, Massachusetts))から「VCA−2500XE」の商品名で入手可能なビデオ接触角分析機を使用して接触角の測定を行う。報告する値は、少なくとも3滴で各液滴の両側で測定される測定の平均である。液滴の容積は、静的測定では5マイクロリットル、前進および後退測定では1〜3マイクロリットルである。
40〜60ナノメートル(nm)の乾燥厚さを提供するため、シリンジポンプを使用して溶液をダイに計量供給し、重合性組成物を基材S1又はS2上にコーティングする。慣用的な空気浮遊オーブン内で65℃に加熱して溶媒を除去した後、100万分の50部(50ppm)未満の酸素を有し、全出力で運転するメリーランド州ゲイサースバーグ、フュージョンUVシステムズ(Fusion UV Systems, Gaithersburg, Maryland)製の600ワットのH型バルブを収納する硬化チャンバに毎分3メートルのライン速度で送り通過させる。
コーティングブロックを使用して127マイクロメートルの湿潤厚さで重合性組成物を基材S1又はS2上にコーティングする。120℃の温度で運転するオーブン内で10分間、溶媒を除去する。次に、コーティングを窒素下で35フィート/分(11メートル/分)のライン速度で、メリーランド州ゲイサースバーグ、フュージョンUVシステムズ(Fusion UV Systems, Gaithersburg, Maryland)から入手可能な全出力で運転する600ワット(600ジュール/秒)の「D型」バルブを使用して硬化させた。
1リットルの丸底フラスコにFC−1、291.24g(0.2405mol)、およびAM−1、21.2g(0.2405mol)を共に室温で投入し、濁った溶液を得た。フラスコに渦流を生じさせ、混合物の温度が45℃に上昇して無色透明の液体が得られ、それを55℃で一晩加熱した。次いで、生成物を75℃で28インチHgの減圧のロータリーエバポレータにかけてメタノールを除去し、公称分子量=1267.15g/molの粘稠で僅かに黄色の液体(即ち、FC−1/AM−1)301.88gを得た。
FC−1/AM−1の調製手順に従ったが、AM−1の代わりにAM−2を使用し、FC−1、50g(41.29mmol)をAM−2、3.64g(41.29mmol)と混合して、公称分子量=1267.15g/molのFC−1/AM−2を得た。
FC−1/AM−1の調製手順に従ったが、AM−1の代わりにAM−3を使用し、FC−1、300g(0.2477mol)とAM−3、25.8g(0.2477mol)を反応させ、公称分子量=1283.15g/molのFC−1/AM−3、312.0gを得た。
FC−1/AM−1の調製手順に従ったが、AM−1の代わりにAM−4を使用し、FC−1、50g(41.29mmol)をAM−4、4.80g(20.64mmol)と混合して濃縮し、公称分子量2590.4、公称当量=647.6g/molのFC−1/AM−4を得た。
マグネチックスターラー(magnetic stirbar)を装備した100mLの丸底フラスコにAM−5、9.92g(165mmol)を投入した。次に、FC−1、20g(16.5mmol)を室温で約1時間にわたってフラスコに加えた。更に1時間攪拌した後、130℃までの温度で2.5mmの圧力で揮発物質を除去し、公称分子量1239.1g/molのFC−1/AM−5を得た。
マグネチックスターラー(magnetic stirbar)を装備した50mLの丸底フラスコにAM−7、6.12g(82.6mmol)およびFC−1、20g(16.5mmol)を室温で投入した。次に、混合物を約30分間室温で攪拌した。最後に150℃までの温度で4.0mmの圧力で揮発物質を除去し、公称分子量1253.1g/molのFC−1/AM−7を得た。
FC−1/AM−1の調製手順に従ったが、FC−1の代わりにFC−2を使用し、FC−2、20g(20meq)をAM−1、1.76g(20meq)と混合して濃縮し、公称分子量2112.3、公称当量=1056.15g/molのFC−2/AM−1を得た。
マグネチックスターラー(magnetic stirbar)を装備した100mLのフラスコにAM−6、7.51g(0.1mol)およびフェノチアジン1.8mgを投入した。次に、AC−1、29.61g(0.1mol)を23℃で等圧滴下ロート(pressure−equalizing funnel)を介して加えた。反応温度は51℃に上昇し、次いで元のように室温まで降下し、公称分子量371.1g/molのAM−6/AC−1を得た。
この実施例は、FC−1/AM−1のAC−1とのモル比約1:1の付加物(FC−1/AM−1/AC−1)の調製を説明する。
AC−1、20%
次式を有すると考えられる一付加物(monoadduct)、40%
二付加物(diadduct)、40%。
この実施例は、FC−1/AM−1のAC−2とのモル比約1:1の付加物(FC−1/AM−1/AC−2)の調製を説明する。
この実施例は、FC−1/AM−1のAC−4とのモル比約1:1の付加物(FC−1/AM−1/AC−4)の調製を説明する。
この実施例は、FC−1/AM−1のAC−5とのモル比約1:1の付加物(FC−1/AM−1/AC−5)の調製を説明する。
この実施例は、FC−1/AM−1のAC−6とのモル比1:3の付加物(FC−1/AM−1/AC−6)の調製を説明する。
この実施例は、FC−1/AM−2のAC−1とのモル比約1:1の付加物(FC−1/AM−2/AC−1)の調製を説明する。
この実施例は、FC−1/AM−2のAC−3とのモル比1:1の付加物(FC−1/AM−2/AC−3)の調製を説明する。
この実施例は、FC−1/AM−2のAC−4とのモル比約1:1の付加物(FC−1/AM−2/AC−4)の調製を説明する。
この実施例は、FC−1/AM−2のAC−5とのモル比約1:1の付加物(FC−1/AM−2/AC−5)の調製を説明する。
この実施例は、FC−1/AM−3のAC−1とのモル比約1:1の付加物(FC−1/AM−3/AC−1)の調製を説明する。
この実施例は、FC−1/AM−3のAC−2とのモル比約1:1の付加物(FC−1/AM−3/AC−2)の調製を説明する。
この実施例は、FC−1/AM−3のAC−4とのモル比約1:1の付加物(FC−1/AM−3/AC−3)の調製を説明する。
この実施例は、FC−1/AM−4のAC−1とのモル比約1:4(当量1:1)の付加物(FC−1/AM−4/AC−1)の調製を説明する。
この実施例は、FC−1/AM−5のAC−1とのモル比約1:2(FC−1/AM−5/AC−1)の調製を説明する。
この実施例は、FC−1/AM−7のAC−1とのモル比1:2(FC−1/AM−7/AC−1)の調製を説明する。
この実施例は、FC−2/AM−1のAC−1とのモル比約1:2(当量1:1)の付加物(FC−2/AM−1/AC−1)の調製を説明する。
この実施例は、FC−3とAM−6/AC−1のモル比1:1の付加物(FC−3/AM−6/AC−1)の調製を説明する。
表1に報告する材料および量を使用して、重合性組成物を基材にコーティングした。重合性組成物は全て、総固形分10質量%に希釈した。メチルエチルケトン中固形分10%の光開始剤溶液を使用して、重合性組成物中に光開始剤PI−1を2質量%、又は、PI−2を1質量%含んだ。最終的な総固形分質量%に希釈する前に光開始剤を加えた。PI−1を含有する配合物ではメチルイソブチルケトン、PI−2を含有する配合物ではメチルエチルケトンを使用して、最終的な総固形分質量%への希釈を達成した。前述のコーティング方法1又はコーティング方法2を使用して、各コーティング溶液をコーティング基材にコーティングした。
Claims (3)
- 次式
(F(RfO)xQZ1R1NR2CH2CH2C(=O)Z2)yM(Z3C(=O)CR3=CH2)z
又は
X[((RfO)xQZ1R1NR2CH2CH2C(=O)Z2)yM(Z3C(=O)CR3=CH2)z]b
(式中、
各Rfは、独立して、1〜6個の炭素原子を有するフッ素化アルキレン基を表し、
各xは、独立して、2以上の整数を表し、
各Qは、独立して、−CF2−、−CF(CF3)−、−CF2CF2−、−CF2CF2CF2−、−CF2CF(CF3)−、−CF(CF3)CF2−、−CF2CF2CH2−、−CF2CH2−、−CF2CF2C(=O)−、−CF2C(=O)−、−CF(CF3)C(=O)−、−CF(CF3)CH2−、1〜6個の炭素原子を有するアルキレン基、又は1〜6個の炭素原子を有するヘテロアルキレン基を表し、
各Z1、Z2およびZ3は、独立して、−S−、−O−、−NH−、又は−NR2−を表し、
各R1は、独立して、アルキレン基、アラルキレン基、又はヘテロアルキレン基を表し、
各R2は、独立して、H、1〜6個の炭素原子を有するアルキル基、−CH2CH2C(=O)Z2M(Z3C(=O)CR3=CH2)z、又は−R1Z1Q(ORf)xFを表し、
各R3は、独立して、H、F、又はメチルを表し、
各yおよびzは、独立して、1以上の整数を表し、
各Mは、y+z価の多価有機基を表し、
Xは、b価の多価有機基を表し、
bは、2以上の整数を表す)
で示される少なくとも1種類の化合物を含む重合性組成物。 - 反応性フッ素化ポリエーテル、および
ポリ(メタ)アクリル化合物、
を混合してそれらのマイケル型付加物を形成することを含む、重合性組成物の製造方法であって、前記マイケル型付加物が少なくとも1つの(メタ)アクリル基を有し、前記反応性フッ素化ポリエーテルが次式
F(RfO)xQZ1R1NR2H
又は
X(RfO)xQZ1R1NR2H
(式中、
各Rfは、独立して、1〜6個の炭素原子を有するフッ素化アルキレン基を表し、
各xは、独立して、2以上の整数を表し、
各Qは、独立して、−CF2−、−CF(CF3)−、−CF2CF2−、−CF2CF2CF2−、−CF2CF(CF3)−、−CF(CF3)CF2−、−CF2CF2CH2−、−CF2CH2−、−CF2CF2C(=O)−、−CF2C(=O)−、−CF(CF3)C(=O)−、−CF(CF3)CH2−、1〜6個の炭素原子を有するアルキレン基、又は1〜6個の炭素原子を有するヘテロアルキレン基を表し、
Z1は、−S−、−O−、−NH−、又は−NR2−を表し、
R1は、アルキレン基、アラルキレン基、又はヘテロアルキレン基を表し、
R2は、独立して、H、又は1〜6個の炭素原子を有するアルキルを表し、
Xは、多価有機基を表す)
で示される方法。 - 次式
(F(RfO)xQZ1R1NR2CH2CH2C(=O)Z2)yM(Z3C(=O)CR3=CH2)z
又は
X[((RfO)xQZ1R1NR2CH2CH2C(=O)Z2)yM(Z3C(=O)CR3=CH2)z]b
(式中、
各Rfは、独立して、1〜6個の炭素原子を有するフッ素化アルキレン基を表し、
各xは、独立して、2以上の整数を表し、
各Qは、独立して、−CF2−、−CF(CF3)−、−CF2CF2−、−CF2CF2CF2−、−CF2CF(CF3)−、−CF(CF3)CF2−、−CF2CF2CH2−、−CF2CH2−、−CF2CF2C(=O)−、−CF2C(=O)−、−CF(CF3)C(=O)−、−CF(CF3)CH2−、1〜6個の炭素原子を有するアルキレン基、又は1〜6個の炭素原子を有するヘテロアルキレン基を表し、
各Z1、Z2およびZ3は、独立して、−S−、−O−、−NH−、又は−NR2−を表し、
各R1は、独立して、アルキレン基、アラルキレン基、又はヘテロアルキレン基を表し、
各R2は、独立して、H、1〜6個の炭素原子を有するアルキル基、−CH2CH2C(=O)Z2M(Z3C(=O)CR3=CH2)z、又は−R1Z1Q(ORf)xFを表し、
各R3は、独立して、H、F、又はメチルを表し、
各yおよびzは、独立して、1以上の整数を表し、
各Mは、y+z価の多価有機基を表し、
Xは、b価の多価有機基を表し、
bは、2以上の整数を表す)
によって記載される少なくとも1種類の化合物を含む重合性組成物を少なくとも部分的に重合させることによって調製可能な防汚組成物を基材の少なくとも一部に有する基材を備える、複合物品。
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ATE412685T1 (de) | 2008-11-15 |
DE602005010683D1 (de) | 2008-12-11 |
KR20070010078A (ko) | 2007-01-19 |
EP1742985B1 (en) | 2008-10-29 |
CN1950427A (zh) | 2007-04-18 |
WO2005113642A1 (en) | 2005-12-01 |
KR101187124B1 (ko) | 2012-09-28 |
TWI389965B (zh) | 2013-03-21 |
US7342080B2 (en) | 2008-03-11 |
JP2007536393A (ja) | 2007-12-13 |
EP1742985A1 (en) | 2007-01-17 |
CN100549064C (zh) | 2009-10-14 |
US20050250921A1 (en) | 2005-11-10 |
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