JP3957716B2 - 重合体膜の製造方法 - Google Patents
重合体膜の製造方法 Download PDFInfo
- Publication number
- JP3957716B2 JP3957716B2 JP2004539101A JP2004539101A JP3957716B2 JP 3957716 B2 JP3957716 B2 JP 3957716B2 JP 2004539101 A JP2004539101 A JP 2004539101A JP 2004539101 A JP2004539101 A JP 2004539101A JP 3957716 B2 JP3957716 B2 JP 3957716B2
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- Prior art keywords
- polymer film
- active energy
- energy ray
- group
- polymerization
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- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- 229910021392 nanocarbon Inorganic materials 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- SFBTTWXNCQVIEC-UHFFFAOYSA-N o-Vinylanisole Chemical compound COC1=CC=CC=C1C=C SFBTTWXNCQVIEC-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 229920002601 oligoester Polymers 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 150000007524 organic acids Chemical group 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- MMSLOZQEMPDGPI-UHFFFAOYSA-N p-Mentha-1,3,5,8-tetraene Chemical compound CC(=C)C1=CC=C(C)C=C1 MMSLOZQEMPDGPI-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl 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])[H] 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- JXIWJBWMQXDALU-UHFFFAOYSA-N phenyl-[2-(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)C1=CC=CC=C1 JXIWJBWMQXDALU-UHFFFAOYSA-N 0.000 description 1
- 239000004038 photonic crystal Substances 0.000 description 1
- STIABRLGDKHASC-UHFFFAOYSA-N phthalic acid;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C1=CC=CC=C1C(O)=O STIABRLGDKHASC-UHFFFAOYSA-N 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001046 rapid expansion of supercritical solution Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000001016 thiazine dye Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- OKYDCMQQLGECPI-UHFFFAOYSA-N thiopyrylium Chemical class C1=CC=[S+]C=C1 OKYDCMQQLGECPI-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- XOALFFJGWSCQEO-UHFFFAOYSA-N tridecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C=C XOALFFJGWSCQEO-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- ZYPZVOKVDNSKLP-UHFFFAOYSA-N tris(4-aminophenyl) phosphate Chemical compound C1=CC(N)=CC=C1OP(=O)(OC=1C=CC(N)=CC=1)OC1=CC=C(N)C=C1 ZYPZVOKVDNSKLP-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000011882 ultra-fine particle Substances 0.000 description 1
- 229920006305 unsaturated polyester Polymers 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
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- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
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- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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- Chemical & Material Sciences (AREA)
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- Organic Chemistry (AREA)
- Polymerisation Methods In General (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Materials For Photolithography (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
活性エネルギー線の照射量(J/cm2)=活性エネルギー線の強度(W/cm2×照射時間(sec)
で定義される。
一般式(1)中のmは、単独で硬化膜を形成する点から、2〜6の整数であることが好ましい。
上記一般式(1)で表わされるマレイミド系化合物は、例えば、カルボキシル基を有するマレイミド化合物と、カルボキシル基と反応する化合物とから公知の方法により合成することができる。カルボキシル基と反応する化合物としては、例えば、直鎮アルキレン基、分枝アルキレン基、シクロアルキレン基およびアリール基からなる群より選ばれる少なくとも1つの炭化水素基が、エーテル結合および/またはエステル結合で結合された一つあるいはそれらの繰り返し単位を有する平均分子量100〜1,000,000の2〜6官能のポリオールまたはポリエポキシドなどが挙げられる。
反応器内壁に設けられた凹部の底に石英耐圧窓を有する、容積30cm3の耐圧反応器に、重合前駆体としてポリエーテルビスマレイミド酢酸エステル(大日本インキ化学工業株式会社製、MIA−200)1.5gを仕込んだ。次に、反応器内を撹拌しながら、二酸化炭素をボンベ圧(約7MPa)で反応器内に導入した後、35℃に昇温し、さらに二酸化炭素を反応器内の圧力が30MPaになるように加圧ポンプで導入して超臨界状態とした。重合前駆体であるポリエーテルビスマレイミド酢酸エステルの仕込み濃度は2質量%であった。
基材としてPETフィルムを反応器内壁に設けられた凹部に押し込み、石英耐圧窓に密着させて固定した。そして、実施例1と同様にして光重合を行ったところ、PETフィルム上に重合体膜が形成された。PETフィルム上に形成された重合体膜は密着性が高く、容易に剥がすことができなかった。
マスクパターンを石英耐圧窓の外側に貼り合わせ、このマスクパターンを介して紫外線を反応器内へ照射した以外は実施例1と同様にして光重合を行ったところ、石英耐圧窓の紫外線が透過した部分上に、マスクパターンが転写された重合体膜が形成された。
実施例1と同様にして光重合を行った後、10分間で急激に二酸化炭素を反応器外に放出し、反応器内を大気圧にまで減圧した。得られた重合体膜を光学顕微鏡で観察したところ、多孔質であった。
重合温度を18℃、圧力を4MPaにした以外は実施例1と同様にして光重合を行ったところ、石英耐圧窓上に重合体膜は形成されなかった。なお、紫外線照射中の二酸化炭素は液体状態であった。
重合溶媒としてアセトンを用いた以外は実施例1と同様にして光重合を行ったところ、石英耐圧窓上に重合体膜は形成されなかった。
重合前駆体としてメタクリル酸メチル4.095gを用い、光重合開始剤として2−ベンジル−2−ジメチルアミノ−1−(4−モルフォリノフェニル)−ブタン−1−オン0.123g、1−ヒドロキシシクロヘキシルフェニルケトン0.123gを用いた以外は実施例1と同様にして光重合を行ったところ、反応器中には重合体微粒子が生成していた。なお、重合前駆体であるメタクリル酸メチルの仕込み濃度は15質量%であった。
反応器内壁に設けられた凹部の底に石英耐圧窓を有する、容積30cm3の耐圧反応器に、重合前駆体としてポリエーテルビスマレイミド酢酸エステル(大日本インキ化学工業株式会社製、MIA−200)0.872gを仕込んだ。次に、反応器内を撹拌しながら、二酸化炭素をボンベ圧(約7MPa)で反応器内に導入した後、35℃に昇温し、さらに二酸化炭素を反応器内の圧力が30MPaになるように加圧ポンプで導入して超臨界状態とした。重合前駆体であるポリエーテルビスマレイミド酢酸エステルの仕込み濃度は3.5質量%であった。
紫外線の照射条件は、照射強度33mW/cm2で照射時間152秒間として、紫外線の照射量を5J/cm2とした以外は実施例6と同様にして光重合を行ったところ、石英耐圧窓上に、紫外線の照射方向、すなわち基材表面に対して垂直方向に成長した突起部を含む重合体膜が形成された。
紫外線の照射条件は、照射強度33mW/cm2で照射時間303秒間として、紫外線の照射量を10J/cm2とした以外は実施例6と同様にして光重合を行ったところ、石英耐圧窓上に、紫外線の照射方向、すなわち基材表面に対して垂直方向に成長した突起部を含む重合体膜が形成された。
紫外線の照射条件は、照射強度33mW/cm2で照射時間1515秒間として、紫外線の照射量を50J/cm2とした以外は実施例6と同様にして光重合を行ったところ、石英耐圧窓上に、重合体膜が形成された。
マスクパターンを石英耐圧窓の外側に貼り合わせ、このマスクパターンを介して紫外線を反応器内へ照射した以外は実施例8と同様にして光重合を行ったところ、石英耐圧窓の紫外線が透過した部分上に、マスクパターンが転写された突起部を含む重合体膜が形成された。
2 二酸化炭素供給用ポンプ
3 反応器
4 温度制御手段
5 窓
5' 窓
6 光源
7 減圧弁
8 活性エネルギー線透過基材
9 マグネチックスターラー
10 撹拌子
11 基材
12 重合体膜
Claims (16)
- 超臨界流体中または亜臨界流体中において、活性エネルギー線の照射により、1種以上の光重合性重合前駆体を光重合するに際し、前記超臨界流体または前記亜臨界流体を重合溶媒として用いて前記重合前駆体の仕込み濃度を1質量%〜70質量%とすることを特徴とする重合体膜の製造方法。
- 前記超臨界流体または亜臨界流体が、超臨界二酸化炭素または亜臨界二酸化炭素である請求項1に記載の重合体膜の製造方法。
- 圧力5MPa以上、温度20℃以上の二酸化炭素中において、前記光重合性重合前駆体を光重合する請求項1に記載の重合体膜の製造方法。
- 圧力7MPa以上、温度30℃以上の二酸化炭素中において、前記光重合性重合前駆体を光重合する請求項1に記載の重合体膜の製造方法。
- 前記光重合性重合前駆体が自発光重合性化合物である請求項1〜4のいずれかに記載の重合体膜の製造方法。
- 前記光重合性重合前駆体が、末端にマレイミド基を少なくとも1つ有するマレイミド系化合物である請求項1〜5のいずれかに記載の重合体膜の製造方法。
- 前記活性エネルギー線が、紫外線、可視光線または近赤外線である請求項1〜6のいずれかに記載の重合体膜の製造方法。
- 超臨界流体または亜臨界流体に曝されるように配置された活性エネルギー線透過基材上に重合体膜を形成する請求項1〜7のいずれかに記載の重合体膜の製造方法。
- 活性エネルギー線の入射面が超臨界流体または亜臨界流体に曝されず、活性エネルギー線の出射面が超臨界流体または亜臨界流体に曝されるように配置された活性エネルギー線透過基材を透過させて活性エネルギー線を照射することにより、1種以上の光重合性重合前駆体を光重合し、前記活性エネルギー線透過基材の活性エネルギー線出射面上に重合体膜を形成する請求項8に記載の重合体膜の製造方法。
- 前記活性エネルギー線を、マスクパターンを介して前記活性エネルギー線透過基材に照射することにより、前記活性エネルギー線透過基材の活性エネルギー線出射面の活性エネルギー線が透過した部分上に選択的に重合体膜を形成する請求項9に記載の重合体膜の製造方法。
- 製造される重合体膜が突起部を含む重合体膜である請求項1〜7のいずれかに記載の重合体膜の製造方法。
- 製造される重合体膜の突起部の高さが、その突起部の径の0.1倍以上である請求項11に記載の重合体膜の製造方法。
- 製造される重合体膜の突起部の高さが10nm以上である請求項11または12に記載の重合体膜の製造方法。
- 超臨界流体または亜臨界流体に曝されるように配置された活性エネルギー線透過基材上に突起部を含む重合体膜を形成する請求項11〜13のいずれかに記載の重合体膜の製造方法。
- 活性エネルギー線の入射面が超臨界流体または亜臨界流体に曝されず、活性エネルギー線の出射面が超臨界流体または亜臨界流体に曝されるように配置された活性エネルギー線透過基材を透過させて活性エネルギー線を照射することにより、1種以上の光重合性重合前駆体を光重合し、前記活性エネルギー線透過基材の活性エネルギー線出射面上に突起部を含む重合体膜を形成する請求項14に記載の重合体膜の製造方法。
- 前記活性エネルギー線を、マスクパターンを介して前記活性エネルギー線透過基材に照射することにより、前記活性エネルギー線透過基材の活性エネルギー線出射面の活性エネルギー線が透過した部分上に選択的に突起部を含む重合体膜を形成する請求項15に記載の重合体膜の製造方法。
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TWI270555B (en) | 2007-01-11 |
US7081486B2 (en) | 2006-07-25 |
CN1298747C (zh) | 2007-02-07 |
KR100570952B1 (ko) | 2006-04-13 |
EP1598374A1 (en) | 2005-11-23 |
AU2003292837A1 (en) | 2004-09-17 |
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