JP5187471B2 - 含フッ素硬化性樹脂、活性エネルギー線硬化性組成物及びその硬化物 - Google Patents
含フッ素硬化性樹脂、活性エネルギー線硬化性組成物及びその硬化物 Download PDFInfo
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- JP5187471B2 JP5187471B2 JP2012551409A JP2012551409A JP5187471B2 JP 5187471 B2 JP5187471 B2 JP 5187471B2 JP 2012551409 A JP2012551409 A JP 2012551409A JP 2012551409 A JP2012551409 A JP 2012551409A JP 5187471 B2 JP5187471 B2 JP 5187471B2
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- Prior art keywords
- fluorine
- curable resin
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- meth
- acrylate
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- 229920005989 resin Polymers 0.000 title claims abstract description 121
- 239000011347 resin Substances 0.000 title claims abstract description 121
- 239000011737 fluorine Substances 0.000 title claims abstract description 105
- 229910052731 fluorine Inorganic materials 0.000 title claims abstract description 105
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 100
- 239000000203 mixture Substances 0.000 title claims abstract description 64
- 239000000178 monomer Substances 0.000 claims abstract description 82
- 125000001033 ether group Chemical group 0.000 claims abstract description 48
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims abstract description 38
- 229920000642 polymer Polymers 0.000 claims abstract description 33
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 22
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- -1 3-mercaptobutyloxyethyl Chemical group 0.000 claims description 84
- 150000001875 compounds Chemical class 0.000 claims description 44
- 239000000463 material Substances 0.000 claims description 40
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 14
- 150000003573 thiols Chemical class 0.000 claims description 14
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 8
- 238000007334 copolymerization reaction Methods 0.000 claims description 8
- 230000001678 irradiating effect Effects 0.000 claims description 8
- 239000007983 Tris buffer Substances 0.000 claims description 5
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- VTLHIRNKQSFSJS-UHFFFAOYSA-N [3-(3-sulfanylbutanoyloxy)-2,2-bis(3-sulfanylbutanoyloxymethyl)propyl] 3-sulfanylbutanoate Chemical compound CC(S)CC(=O)OCC(COC(=O)CC(C)S)(COC(=O)CC(C)S)COC(=O)CC(C)S VTLHIRNKQSFSJS-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- XVKLLVZBGMGICC-UHFFFAOYSA-N o-[3-propanethioyloxy-2,2-bis(propanethioyloxymethyl)propyl] propanethioate Chemical compound CCC(=S)OCC(COC(=S)CC)(COC(=S)CC)COC(=S)CC XVKLLVZBGMGICC-UHFFFAOYSA-N 0.000 claims description 2
- 230000003373 anti-fouling effect Effects 0.000 abstract description 50
- 239000012298 atmosphere Substances 0.000 abstract description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 16
- 239000001301 oxygen Substances 0.000 abstract description 16
- 229910052760 oxygen Inorganic materials 0.000 abstract description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 111
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- 238000006116 polymerization reaction Methods 0.000 description 25
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- 230000000052 comparative effect Effects 0.000 description 21
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
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- 238000006243 chemical reaction Methods 0.000 description 16
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 13
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 10
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- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 10
- SJBBXFLOLUTGCW-UHFFFAOYSA-N 1,3-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(C(F)(F)F)=C1 SJBBXFLOLUTGCW-UHFFFAOYSA-N 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000004793 Polystyrene Substances 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
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- 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 7
- 230000005764 inhibitory process Effects 0.000 description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229940059574 pentaerithrityl Drugs 0.000 description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 7
- 239000005056 polyisocyanate Substances 0.000 description 7
- 229920001228 polyisocyanate Polymers 0.000 description 7
- 239000007870 radical polymerization initiator Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- 239000003822 epoxy resin Substances 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 6
- 229920000647 polyepoxide Polymers 0.000 description 6
- 230000001846 repelling effect Effects 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
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- 238000010894 electron beam technology Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
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- 239000004973 liquid crystal related substance Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000011907 photodimerization Methods 0.000 description 5
- 239000003504 photosensitizing agent Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- 102100026735 Coagulation factor VIII Human genes 0.000 description 4
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 230000003669 anti-smudge Effects 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000007405 data analysis Methods 0.000 description 4
- 239000012024 dehydrating agents Substances 0.000 description 4
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- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 4
- 239000002649 leather substitute Substances 0.000 description 4
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- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
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- 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 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 3
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- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C08F114/16—Monomers containing bromine or iodine
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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
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/334—Polymers modified by chemical after-treatment with organic compounds containing sulfur
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
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Description
方法1:ポリ(パーフルオロアルキレンエーテル)鎖の両末端に水酸基を1つずつ有する化合物に対して(メタ)アクリル酸クロライドを脱塩酸反応させて得る方法。
方法2:ポリ(パーフルオロアルキレンエーテル)鎖の両末端に水酸基を1つずつ有する化合物に対して(メタ)アクリル酸を脱水反応させて得る方法。
方法3:ポリ(パーフルオロアルキレンエーテル)鎖の両末端に水酸基を1つずつ有する化合物に対して2−(メタ)アクリロイルオキシエチルイソシアネートをウレタン化反応させて得る方法。
方法4:ポリ(パーフルオロアルキレンエーテル)鎖の両末端に水酸基を1つずつ有する化合物に対して無水イタコン酸をエステル化反応させて得る方法。
方法5:ポリ(パーフルオロアルキレンエーテル)鎖の両末端に水酸基を1つずつ有する化合物に対してクロロメチルスチレンを脱塩酸反応させて得る方法。
方法6:ポリ(パーフルオロアルキレンエーテル)鎖の両末端に水酸基を1つずつ有する化合物に対して(メタ)アクリル酸無水物をエステル化反応させる方法。
方法7:ポリ(パーフルオロアルキレンエーテル)鎖の両末端にカルボキシル基を1つずつ有する化合物に対して4−ヒドロキシブチル(メタ)アクリレートグリシジルエーテルをエステル化反応させて得る方法。
方法8:ポリ(パーフルオロアルキレンエーテル)鎖の両末端にカルボキシル基を1つずつ有する化合物に対してグリシジル(メタ)アクリレートをエステル化反応させて得る方法。
方法9:ポリ(パーフルオロアルキレンエーテル)鎖の両末端にイソシアネート基を1つずつ有する化合物に対して2−ヒドロキシエチル(メタ)アクリレートを反応させて得る方法。
方法10:ポリ(パーフルオロアルキレンエーテル)鎖の両末端にイソシアネート基を1つずつ有する化合物に対して2−ヒドロキシエチル(メタ)アクリルアミドを反応させる方法。
方法11:ポリ(パーフルオロアルキレンエーテル)鎖の両末端にエポキシ基を1つずつ有する化合物に対して(メタ)アクリル酸をエステル化反応させる方法。
測定装置:東ソー株式会社製「HLC−8220 GPC」、
カラム:東ソー株式会社製ガードカラム「HHR−H」(6.0mmI.D.×4cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
検出器:ELSD(オルテック製「ELSD2000」)
データ処理:東ソー株式会社製「GPC−8020モデルIIデータ解析バージョン4.30」
測定条件:カラム温度 40℃
展開溶媒 テトラヒドロフラン(THF)
流速 1.0ml/分
試料:樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(5μl)。
標準試料:前記「GPC−8020モデルIIデータ解析バージョン4.30」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
東ソー株式会社製「A−500」
東ソー株式会社製「A−1000」
東ソー株式会社製「A−2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
東ソー株式会社製「F−40」
東ソー株式会社製「F−80」
東ソー株式会社製「F−128」
東ソー株式会社製「F−288」
東ソー株式会社製「F−550」
装置:フーリエ変換赤外分光装置(サーモエレクトロン株式会社製「NICOLET380」)
方法:KBr法
装置:日本電子株式会社製「AL−400」
溶媒:クロロホルム−d
測定装置:東ソー株式会社製「HLC−8220 GPC」、
カラム:東ソー株式会社製ガードカラム「HHR−H」(6.0mmI.D.×4cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
+東ソー株式会社製「TSK−GEL GMHHR−N」(7.8mmI.D.×30cm)
検出器:ELSD(オルテック製「ELSD2000」)
データ処理:東ソー株式会社製「GPC−8020モデルIIデータ解析バージョン4.30」
測定条件:カラム温度 40℃
展開溶媒 テトラヒドロフラン(THF)
流速 1.0ml/分
試料:樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(5μl)。
標準試料:前記「GPC−8020モデルIIデータ解析バージョン4.30」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
東ソー株式会社製「A−500」
東ソー株式会社製「A−1000」
東ソー株式会社製「A−2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
東ソー株式会社製「F−40」
東ソー株式会社製「F−80」
東ソー株式会社製「F−128」
東ソー株式会社製「F−288」
東ソー株式会社製「F−550」
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、下記式(a2−1−1)で表されるポリ(パーフルオロアルキレンエーテル)鎖を有し、その両末端に水酸基を有する化合物20質量部、溶媒として1,3−ビス(トリフルオロメチル)ベンゼン10質量部、重合禁止剤としてp−メトキシフェノール0.02質量部及び中和剤としてトリエチルアミン1.5質量部を仕込み、空気気流下にて攪拌を開始し、フラスコ内を10℃に保ちながらメタクリル酸クロライド1.3質量部を1時間かけて滴下した。滴下終了後、10℃で1時間攪拌し、昇温して30℃で1時間攪拌して、さらに50℃に昇温して10時間撹拌した後、ガスクロマトグラフィー測定にてメタクリル酸クロライドの消失を確認し反応を終了した。次いで、溶媒として1,3−ビス(トリフルオロメチル)ベンゼン70質量部を追加した後、イオン交換水80質量部を混合して攪拌してから静置し水層を分離させて取り除く方法による洗浄を3回繰り返した。次いで、重合禁止剤としてp−メトキシフェノール0.02質量部を添加し、脱水剤として硫酸マグネシウム8質量部を添加して1日間静置することで完全に脱水した後、脱水剤を濾別した。
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、下記式(a2−1−2)で表されるポリ(パーフルオロアルキレンエーテル)鎖を有し、その両末端に水酸基を有する化合物20質量部、溶媒としてジイソプロピルエーテル20質量部、重合禁止剤としてp−メトキシフェノール0.02質量部及び中和剤としてトリエチルアミン3.1質量部を仕込み、空気気流下にて攪拌を開始し、フラスコ内を10℃に保ちながらメタクリル酸クロライド2.7質量部を1時間かけて滴下した。滴下終了後、10℃で1時間攪拌し、昇温して30℃で1時間攪拌して、さらに50℃に昇温して10時間撹拌した後、ガスクロマトグラフィー測定にてメタクリル酸クロライドの消失を確認し反応を終了した。次いで、溶媒としてジイソプロピルエーテル40質量部を追加した後、イオン交換水80質量部を混合して攪拌してから静置し水層を分離させて取り除く方法による洗浄を3回繰り返した。次いで、重合禁止剤としてp−メトキシフェノール0.02質量部を添加し、脱水剤として硫酸マグネシウム8質量部を添加して1日間静置することで完全に脱水した後、脱水剤を濾別した。
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、溶媒としてメチルイソブチルケトン425質量部と1,3−ビス(トリフルオロメチル)ベンゼン1,305質量部を仕込み、窒素気流下にて攪拌しながら95℃に昇温した。次いで、上記合成例1で得られた単量体(A−2−1)209質量部を1,3−ビス(トリフルオロメチル)ベンゼン145質量部に溶解した溶液(液1)と、3,4,5,6−テトラヒドロフタルイミドエチルアクリレート836質量部をメチルイソブチルケトン643質量部及び1,3−ビス(トリフルオロメチル)ベンゼン200質量部の混合溶媒に溶解した溶液(液2)と、ラジカル重合開始剤であるt−ブチルペルオキシ−2−エチルヘキサノエート11質量部及び下記式(B−1)で表されるペンタエリスリトールテトラキス(3−メルカプトブチレート)53質量部をメチルイソブチルケトン420質量部に溶解した溶液(液3)の3種類の滴下液をそれぞれ別々の滴下装置にセットし、フラスコ内を95℃に保ちながら同時に滴下を開始し、液1と液2は2時間、液3は2時間20分かけて滴下した。滴下終了後、95℃で5時間攪拌した。
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、溶媒として1,3−ビス(トリフルオロメチル)ベンゼン146.1質量部を仕込み、窒素気流下にて攪拌しながら105℃に昇温した。次いで、上記合成例1で得られた単量体(A−2−1)83.5質量部(液1)と、2−ヒドロキシエチルメタクリレート(以下、「HEMA」と略記する。)160質量部(液2)と、ラジカル重合開始剤であるt−ブチルペルオキシ−2−エチルヘキサノエート36.5質量部を1,3−ビス(トリフルオロメチル)ベンゼン306.2質量部に溶解した溶液(液3)の3種類の滴下液をそれぞれ別々の滴下装置にセットし、フラスコ内を105℃に保ちながら同時に2時間かけて滴下した。滴下終了後、105℃で5時間攪拌して、単量体(A−2−1)とHEMAとの共重合体を得た。
撹拌装置、温度計、冷却管、滴下装置を備えた別のガラスフラスコに、溶媒としてメチルイソブチルケトン63質量部を仕込み、窒素気流下にて攪拌しながら105℃に昇温した。次いで、上記合成例2で得られた単量体(A−2−2)21.5質量部(液1)、HEMA41.3質量部(液2)、ラジカル重合開始剤であるt−ブチルペルオキシ−2−エチルヘキサノエート9.4質量部をメチルイソブチルケトン126質量部に溶解した溶液135.4質量部(液3)の3種類の滴下液をそれぞれ別々の滴下装置にセットし、フラスコ内を105℃に保ちながら同時に2時間かけて滴下した。滴下終了後、105℃で10時間攪拌した後、減圧下で溶媒を留去することによって、単量体(A−2−2)とHEMAとの共重合体を得た。
撹拌装置、温度計、冷却管、滴下装置を備えたガラスフラスコに、溶媒としてメチルイソブチルケトン3,275質量部を仕込み、窒素気流下にて攪拌しながら105℃に昇温した。次いで、上記合成例2で得られた単量体(A−2−2)191質量部(液1)、3,4,5,6−テトラヒドロフタルイミドエチルアクリレート762質量部をメチルイソブチルケトン1,288質量部に溶解した溶液(液2)、ラジカル重合開始剤であるt−ブチルペルオキシ−2−エチルヘキサノエート143質量部をメチルイソブチルケトン835質量部に溶解した溶液(液3)の3種類の滴下液をそれぞれ別々の滴下装置にセットし、フラスコ内を105℃に保ちながら同時に2時間かけて滴下した。滴下終了後、105℃で10時間攪拌した。
5官能無黄変型ウレタンアクリレート50質量部、ジペンタエリスリトールヘキサアクリレート50質量部、酢酸ブチル25質量部、光重合開始剤として1−ヒドロキシシクロヘキシルフェニルケトン(BASFジャパン株式会社製「イルガキュア184」)5質量部、溶剤としてトルエン54質量部、2−プロパノール28質量部、酢酸エチル28質量部、プロピレングリコールモノメチルエーテル28質量部を混合し溶解させて、活性エネルギー線硬化性組成物のベース樹脂組成物を得た。
上記で得られたベース樹脂組成物268質量部に、実施例1、実施例2で得られた含フッ素硬化性樹脂の溶液及び比較例1〜4で得られた比較対照用含フッ素硬化性樹脂の溶液を樹脂分として1質量部となる量を加えて均一に混合して、活性エネルギー線硬化性組成
物1、2及び比較対照用活性エネルギー線硬化性組成物1´〜4´を得た。次いで、これらの活性エネルギー線硬化性組成物をバーコーターNo.13を用いて、厚さ188μmのポリエチレンテレフタレート(PET)フィルムに塗布した後、60℃の乾燥機に5分間入れて溶剤を揮発させ、紫外線硬化装置にて紫外線(UV)を照射して硬化させ、硬化塗膜が積層したフィルム(塗工フィルム)を得た。なお、紫外線の照射条件は、空気雰囲気下(酸素濃度21容量%)、高圧水銀灯使用、紫外線照射量3.5kJ/m2とした。
塗工フィルムの塗工表面に、フェルトペン(寺西化学工業株式会社製「マジックインキ大型黒色」)で線を描き、その黒色インクの付着状態を目視で観察することで汚れ付着防止性の評価を行った。なお、評価基準は下記の通りである。
A:防汚性が最も良好で、インクが玉状にはじくもの。
B:インクが玉状にはじかず、線状のはじきが生じるもの(線幅がフェルトペンのペン先の幅の50%未満)。
C:インクの線状のはじきが生じ、線幅がフェルトペンのペン先の幅の50%以上100%未満であったもの。
D:インクがまったくはじかずに表面にきれいに描けてしまうもの。
上記の汚れ付着防止性の試験後、付着したインクを荷重500gにてティッシュペーパーですべて拭き取るのに要した拭き取り回数を測定し、その結果から下記の基準にしたがって汚れ拭き取り容易性を評価した。
A:1回の拭き取りで完全にインクを除去できたもの。
B:2〜10回の拭き取りで完全にインクを除去できたもの。
C:10回の拭き取り操作で完全にはインクを除去できなかったもの。
上記の汚れ拭き取り容易性の試験後、再び、フェルトペン(寺西化学工業株式会社製「マジックインキ大型黒色」)で線を描き、その黒色インクの付着状態を目視で観察することで汚れ付着防止性の評価を行った。なお、評価基準は下記の通りである。
A:防汚性が最も良好で、インクが玉状にはじくもの。
B:インクが玉状にはじかず、線状のはじきが生じるもの(線幅がフェルトペンのペン先の幅の50%未満)。
C:インクの線状のはじきが生じ、線幅がフェルトペンのペン先の幅の50%以上100%未満であったもの。
D:インクがまったくはじかずに表面にきれいに描けてしまうもの。
Claims (10)
- 重合性不飽和基を有する単量体の重合体またはウレタン重合体の重合体構造中にポリ(パーフルオロアルキレンエーテル)鎖、マレイミド基及びメルカプト基を有することを特徴とする含フッ素硬化性樹脂。
- 前記重合体が重合性不飽和基を有する単量体の重合体である請求項1記載の含フッ素硬化性樹脂。
- ポリ(パーフルオロアルキレンエーテル)鎖とその両末端に重合性不飽和基を有する単量体(A)と、マレイミド基及びマレイミド基以外の重合性不飽和基を有する単量体(B)とを必須の単量体成分として、多官能チオール(C)の存在下で共重合させて得られる請求項1記載の含フッ素硬化性樹脂。
- 前記単量体(A)が有する重合性不飽和基が(メタ)アクリロイル基である請求項3記載の含フッ素硬化性樹脂。
- 前記多官能チオール(C)が、ペンタエリスリトールテトラキス(3−メルカプトブチレート)、ペンタエリスリトールテトラキスチオプロピオネート、トリス(3−メルカプトブチルオキシエチル)イソシアヌレート及びジペンタエリスリトールヘキサキスチオプロピオネートからなる群から選ばれる1種以上の化合物である請求項3記載の含フッ素硬化性樹脂。
- 前記多官能チオール(C)の使用量が、重合性不飽和基を有する単量体の合計100質量部に対して0.1〜50質量部の範囲である請求項3記載の含フッ素硬化性樹脂。
- 請求項1〜7のいずれか1項記載の含フッ素硬化性樹脂を、基材に塗布し、活性エネルギー線を照射して硬化させてなることを特徴とする硬化物。
- 請求項1〜7のいずれか1項記載の含フッ素硬化性樹脂、及び、活性エネルギー線硬化性樹脂(D)又は活性エネルギー線硬化性単量体(E)を含有することを特徴とする活性エネルギー線硬化性組成物。
- 請求項9記載の活性エネルギー線硬化性組成物を、基材に塗布し、活性エネルギー線を照射して硬化させてなることを特徴とする硬化物。
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CN103502306A (zh) | 2014-01-08 |
US20140107278A1 (en) | 2014-04-17 |
CN103502306B (zh) | 2016-04-06 |
KR20140037059A (ko) | 2014-03-26 |
TWI547505B (zh) | 2016-09-01 |
WO2012173088A1 (ja) | 2012-12-20 |
TW201305225A (zh) | 2013-02-01 |
US8779065B2 (en) | 2014-07-15 |
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