JP5488188B2 - 含フッ素重合性重合体及びそれを用いた活性エネルギー線硬化型組成物 - Google Patents
含フッ素重合性重合体及びそれを用いた活性エネルギー線硬化型組成物 Download PDFInfo
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- JP5488188B2 JP5488188B2 JP2010110120A JP2010110120A JP5488188B2 JP 5488188 B2 JP5488188 B2 JP 5488188B2 JP 2010110120 A JP2010110120 A JP 2010110120A JP 2010110120 A JP2010110120 A JP 2010110120A JP 5488188 B2 JP5488188 B2 JP 5488188B2
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- acrylate
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- 229920000642 polymer Polymers 0.000 title claims description 109
- 229910052731 fluorine Inorganic materials 0.000 title claims description 80
- 239000011737 fluorine Substances 0.000 title claims description 80
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- 239000000203 mixture Substances 0.000 title claims description 60
- 150000001875 compounds Chemical class 0.000 claims description 121
- -1 carboxylic acid halide Chemical class 0.000 claims description 85
- 238000000576 coating method Methods 0.000 claims description 70
- 239000011248 coating agent Substances 0.000 claims description 69
- 125000000524 functional group Chemical group 0.000 claims description 62
- 239000000178 monomer Substances 0.000 claims description 62
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 48
- 125000000962 organic group Chemical group 0.000 claims description 31
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 26
- 125000003700 epoxy group Chemical group 0.000 claims description 26
- 125000001033 ether group Chemical group 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 24
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 24
- 238000006116 polymerization reaction Methods 0.000 claims description 17
- 150000008065 acid anhydrides Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 238000010526 radical polymerization reaction Methods 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 229910052723 transition metal Inorganic materials 0.000 claims description 9
- 150000003624 transition metals Chemical class 0.000 claims description 9
- 239000003446 ligand Substances 0.000 claims description 8
- 230000000379 polymerizing effect Effects 0.000 claims description 7
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 claims description 6
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical group [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 claims description 5
- 125000005022 dithioester group Chemical group 0.000 claims description 4
- 150000003623 transition metal compounds Chemical class 0.000 claims description 4
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 3
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- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
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- BOZRCGLDOHDZBP-UHFFFAOYSA-N 2-ethylhexanoic acid;tin Chemical compound [Sn].CCCCC(CC)C(O)=O BOZRCGLDOHDZBP-UHFFFAOYSA-N 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
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- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 4
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- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F14/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F14/18—Monomers containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F14/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F259/00—Macromolecular compounds obtained by polymerising monomers on to polymers of halogen containing monomers as defined in group C08F14/00
- C08F259/08—Macromolecular compounds obtained by polymerising monomers on to polymers of halogen containing monomers as defined in group C08F14/00 on to polymers containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/12—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
Description
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(100μl)。
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」
反応容器に下記式(A’−1)で表されるパーフルオロポリエーテルのジアルコール29g、トリエチルアミン4.6g、ジイソプロピルエーテル(以下、「IPE」という。)15gを仕込んで撹拌し、均一な溶液とした。この溶液に2−ブロモイソ酪酸ブロマイド10gを、内温が30℃以上にならないように冷却しながら、75分かけて滴下した。室温下で3時間撹拌後、さらに40℃で15時間撹拌した。次いで、IPE89gで希釈した後、0.1M塩酸100gを加えて撹拌した。得られた反応溶液から、分液により分離した有機層を飽和炭酸水素ナトリウム水及び飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥した。その後、得られた反応溶液をエバポレータで濃縮して、30.7gのパーフルオロポリエーテルブロモイソ酪酸エステル誘導体を得た。
窒素置換した反応容器に、メチルエチルケトン(以下、「MEK」という。)8.2g、2,2’−ビピリジル0.373g、塩化第一銅0.118gを加え、室温下で30分撹拌した。次いで、2−ヒドロキシエチルメタクリレート6.25g、合成例1で得たパーフルオロポリエーテルブロモイソ酪酸エステル誘導体1.98gを加え、窒素気流下、50℃で21時間反応させて重合体溶液を得た。得られた重合体溶液をメタノールで希釈し、水/メタノールで再沈殿精製を行い、白色固体を得た。この固体3.0gをMEK4.1gに溶解し、2−エチルヘキサン酸スズ溶液(0.2質量%MEK溶液)2.1gを加えて60℃に昇温した。液中に乾燥空気を導入しながら、2−アクリロイルオキシエチルイソシアネートのMEK溶液(50質量%)4.66gを滴下し、1時間反応、さらに80℃で4時間反応させた後、MEKで希釈して、含フッ素重合性重合体(1)の40質量%MEK溶液を得た。なお、この含フッ素重合性重合体(1)の分子量をGPCで測定したところ、数平均分子量9,100、重量平均分子量10,500であった。
窒素置換した反応容器に、MEK7.6g、2,2’−ビピリジル0.559g、塩化第一銅0.177gを加え、室温下で30分撹拌した。次いで、2−ヒドロキシエチルメタクリレート4.72g、合成例1で得たパーフルオロポリエーテルブロモイソ酪酸エステル誘導体2.96gを加え、窒素気流下、50℃で21時間反応させて重合体溶液を得た。得られた重合体溶液をメタノールで希釈し、水/メタノールで再沈殿精製を行い、白色固体を得た。この固体3.0gをMEK4.0gに溶解させ、2−エチルヘキサン酸スズ溶液(0.2重量%MEK溶液)2.1gを加えて60℃に昇温した。液中に乾燥空気を導入しながら、2−アクリロイルオキシエチルイソシアネートのMEK溶液(50質量%)3.74gを滴下し、1時間反応、さらに80℃で4時間反応させ後、MEKで希釈して、含フッ素重合性重合体(2)の40質量%MEK溶液を得た。なお、この含フッ素重合性重合体(2)の分子量をGPCで測定したところ、数平均分子量6,200、重量平均分子量7,700であった。
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(以下、「MIBK」という。)69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、下記式で表されるフッ素化アルキル基含有アクリレート40質量部と2−ヒドロキシエチルメタクリレート28.8質量部とMIBK69質量部とを混合した単量体溶液137.8質量部、ラジカル重合開始剤(t−ブチルペルオキシ−2−エチルヘキサノエート)3.4質量部とMIBK22.5質量部とを混合した重合開始剤溶液25.9質量部の2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3時間かけて滴下した。滴下終了後、105℃で10時間攪拌し、重合体溶液232.7質量部を得た。
本発明において、数平均分子量(Mn)、重量平均分子量(Mw)及び分散度は、GPCによって、下記の条件により測定した。なお、数平均分子量(Mn)及び重量平均分子量(Mw)は、標準ポリスチレン換算の値である。
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(100μl)。
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」
(実施例3〜4、比較例2〜3)
5官能の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(チバスペシャリティーケミカルズ株式会社製「イルガキュア184」;1−ヒドロキシシクロヘキシルフェニルケトン)5質量部、トルエン54質量部、2−プロパノール28質量部、酢酸エチル25質量部及びプロピレングリコールモノメチルエーテル28質量部を均一に混合して、ベースとなる活性エネルギー線硬化型組成物を得た。次いで、このベースとなる活性エネルギー線硬化型組成物265質量部に対して、実施例1〜2及び比較例1で得られた含フッ素重合性重合体を40質量%含有する溶液2.5質量部を加えて均一に混合して、含フッ素重合性重合体を含有する活性エネルギー線硬化型組成物を得た。なお、実施例1〜2及び比較例1で得られた含フッ素重合性重合体を用いた活性エネルギー線硬化型組成物をそれぞれ実施例3〜4及び比較例3とし、含フッ素重合性重合体を加えずにベースの紫外線硬化型組成物のみのものも用意して比較例2とした。
上記で得られた活性エネルギー線硬化型組成物の外観を目視で観察し、含フッ素重合性重合体の相溶性を評価した。
A:透明である。
B:濁りがある。
C:成分の分離が見られる。
(評価用試料の作製)
上記で得られた含フッ素ラジカル重合性共重合体を含有する活性エネルギー線硬化型組成物をバーコーター(No.13)を用いて、ポリエチレンテレフタレート(PET)フィルム(厚さ188μm)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(窒素雰囲気下、高圧水銀灯、紫外線照射量2.0kJ/m2)を用いて硬化させ、塗工フィルムを作製した。また、比較例2として、含フッ素重合性重合体を添加していない活性エネルギー線硬化型組成物についても同様に塗工フィルムを作製した。この塗工フィルムを1日室温で放置後、下記の接触角の測定及び評価、汚れ付着防止性の評価を行った。
AA:防汚性が最も良好で、インクが玉状にはじくもの。
A: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)。
B: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。
C: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。
「汚れ付着防止性」の試験後、荷重1kgにてティッシュペーパーで拭き取った際の様子を下記の基準にて評価した。
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。
Claims (7)
- ポリ(パーフルオロアルキレンエーテル)鎖の両末端にラジカル生成能を有する官能基を有する化合物(A)の両末端に、水酸基、イソシアネート基、エポキシ基、カルボキシル基、カルボン酸ハロゲン化物及び酸無水物からなる群から選ばれる少なくとも1つの反応性基を有する重合性不飽和単量体(B)を必須とする単量体成分を重合させて得られる重合体(C)が有する前記反応性基の一部又は全部に対し、該反応性基と反応して結合を形成する水酸基、イソシアネート基、エポキシ基、カルボキシル基、カルボン酸ハロゲン化物及び酸無水物からなる群から選ばれる少なくとも1つの官能基及び重合性不飽和基を有する化合物(D)を反応することによって得られることを特徴とする含フッ素重合性重合体。
- 前記化合物(A)が有するラジカル生成能を有する官能基が、ハロゲン原子を有する有機基、アルキルテルル基を有する有機基、ジチオエステル基を有する有機基、パーオキシド基を有する有機基又はアゾ基を有する有機基である請求項1記載の含フッ素重合性重合体。
- 前記化合物(A)が有するラジカル生成能を有する官能基が、ハロゲン原子を有する有機基、アルキルテルル基を有する有機基又はジチオエステル基を有する有機基であり、かつ前記化合物(A)に前記単量体(B)を必須の単量体成分として重合させる重合法が、リビングラジカル重合である請求項1記載の含フッ素重合性重合体。
- 前記リビングラジカル重合が、重合開始剤、遷移金属化合物及び該遷移金属と配位結合可能な配位子を有する化合物の存在下で行う原子移動型ラジカル重合である請求項3記載の含フッ素重合性重合体。
- 請求項1〜4のいずれか1項記載の含フッ素重合性重合体を含有することを特徴とする活性エネルギー線硬化型組成物。
- 請求項5記載の活性エネルギー線硬化型組成物を硬化させたことを特徴とする硬化物。
- 請求項5記載の活性エネルギー線硬化型組成物の硬化塗膜を有することを特徴とする物品。
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JP2012206313A (ja) * | 2011-03-29 | 2012-10-25 | Dic Corp | 防汚性硬化塗膜を有する物品及び防汚性フィルム |
US8779065B2 (en) * | 2011-06-17 | 2014-07-15 | Dic Corporation | Fluorine-containing curable resin, active energy beam-curable composition, and cured product thereof |
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WO2014104074A1 (ja) * | 2012-12-28 | 2014-07-03 | 東洋合成工業株式会社 | 硬化性樹脂組成物、インプリント用樹脂モールド、光インプリント方法、半導体集積回路の製造方法及び微細光学素子の製造方法 |
WO2014136731A1 (ja) | 2013-03-04 | 2014-09-12 | 東洋合成工業株式会社 | 組成物、樹脂モールド、光インプリント方法、光学素子の製造方法、及び電子素子の製造方法 |
CN103342793B (zh) * | 2013-05-31 | 2015-08-05 | 成都彭州立源高分子材料有限公司 | 一种有机氟硅杂化光敏树脂及其合成方法 |
WO2017014145A1 (ja) * | 2015-07-23 | 2017-01-26 | Dic株式会社 | 含フッ素化合物、リビング重合開始剤、含フッ素重合体、含フッ素重合体の製造方法及びレジスト組成物 |
US11326069B2 (en) * | 2016-12-26 | 2022-05-10 | Dic Corporation | Fluorine-containing active energy ray curable resin, surfactant, active energy ray curable resin composition, and cured film |
WO2019129691A1 (en) * | 2017-12-26 | 2019-07-04 | Akzo Nobel Coatings International B.V. | A fluorinated ether polymer, the preparation method therefore and use thereof |
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