JP7155017B2 - 光透過度調節フィルム及び光透過度調節フィルム組成物 - Google Patents
光透過度調節フィルム及び光透過度調節フィルム組成物 Download PDFInfo
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- JP7155017B2 JP7155017B2 JP2018563422A JP2018563422A JP7155017B2 JP 7155017 B2 JP7155017 B2 JP 7155017B2 JP 2018563422 A JP2018563422 A JP 2018563422A JP 2018563422 A JP2018563422 A JP 2018563422A JP 7155017 B2 JP7155017 B2 JP 7155017B2
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 68
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- 239000001257 hydrogen Substances 0.000 claims description 52
- 239000000126 substance Substances 0.000 claims description 47
- 229910052736 halogen Inorganic materials 0.000 claims description 45
- 150000002367 halogens Chemical class 0.000 claims description 45
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 26
- 238000006116 polymerization reaction Methods 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 239000003505 polymerization initiator Substances 0.000 claims description 14
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
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- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 3
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- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical group N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
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- G—PHYSICS
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- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
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- G02B26/00—Optical devices or arrangements for the control of light using movable or deformable optical elements
- G02B26/02—Optical devices or arrangements for the control of light using movable or deformable optical elements for controlling the intensity of light
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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
- 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
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
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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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
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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
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- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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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
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- C08G77/442—Block-or graft-polymers containing polysiloxane sequences containing vinyl polymer sequences
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- 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
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- G02B26/00—Optical devices or arrangements for the control of light using movable or deformable optical elements
- G02B26/02—Optical devices or arrangements for the control of light using movable or deformable optical elements for controlling the intensity of light
- G02B26/023—Optical devices or arrangements for the control of light using movable or deformable optical elements for controlling the intensity of light comprising movable attenuating elements, e.g. neutral density filters
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- Medicinal Chemistry (AREA)
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- Manufacturing & Machinery (AREA)
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- Optics & Photonics (AREA)
- Materials Engineering (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Mechanical Light Control Or Optical Switches (AREA)
Description
1-1.コポリマーの製造(実験例PDMS1)
窒素下の室温(約25℃)でジエトキシジメチルシラン 70.08g(473mmol)とジメトキシメチルビニルシラン 2.35g(14.7mmol)(供給モル比=97.0:3.0)を250mlの三口フラスコに入れ、フラスコに重合触媒として蒸留水7.6mlと塩酸1.9ml(37%)を徐々に添加した。次いで、反応温度を約70℃に上昇させた。70ml/分の窒素気流下で約24時間重合反応を行った後、温度を室温に下げた。高粘性の共重合体を200mlのエチル酢酸(EA)に希釈して溶解させた後、重合体EA溶液を700mlの水に入れて触媒を除去した。1日間、水層から重合体EA溶液層を分離した後、残留する水を硫酸マグネシウムを使用して重合体EA溶液から除去した。硫酸マグネシウムを濾過除去し、室温で真空蒸発器によりEAを除去した後、透明な無色高粘性重合体を35℃で2日間真空乾燥して実験例PDMS1を得た。
実験例PDMS1の確認のために、ゲル浸透クロマトグラフィー(gel permeation chromatography、GPC)、フーリエ換算赤外線分光分析(Fourier Transform Infrared spectroscopy、IR)、及び水素核磁気共鳴分光分析(Proton nuclear magnetic resonance spectroscopy、以下、1H-NMR)を行い、収率を計算した。
GPC(THF、標準ポリスチレン):Mn=105,832;PD=1.61。
上記実験例PDMS1と同様の方法でコポリマーを製造した。但し、ジエトキシジメチルシラン 80.01g(540mmol)とジエトキシメチルビニルシラン 5.55g(34.6mmol)(投入モル比=94.0:6.0)を出発物質として使用した。重合触媒として蒸留水8.9mL及び塩酸(37%)2.3mLを加えた。
GPC(THF、標準ポリスチレン):Mn=108,379;PD=1.42
IR vmax(液状、NaCl)/cm-1:3055w(=C-H構造,ビニル);2963s(C-H構造,メチル);1598w(C=C構造,ビニル);1410m(C-H ベンゼン、メチル);1093s(Si-O構造,シロキサン)。1H NMRδH(CDCl3,500MHz):5.92-6.04(2H,m,ビニル);5.78-5.83(H,m,ビニル);0.08-0.11(9H,m,メチル)。
上記実験例PDMS1と同様の方法でコポリマーを製造した。但し、ジエトキシジメチルシラン 75.01g(506mmol)とジエトキシメチルビニルシラン 11.07g(69.1mmol)(投入モル比=88:12)を出発物質として使用した。重合触媒として蒸留水8.8mL及び塩酸(37%)2.3mLを加えた。
実験例PDMS3の収率、ゲル浸透クロマトグラフィー(GPC)、赤外線分光(IR)、及び水素核磁気共鳴分光分析(1H-NMR)を行った。
上述のように製造されたコポリマー及びt-ブチルアクリレート(第1モノマー)を下記表1のように混合して組成物を製造した。
コポリマー及び第1モノマーを下記表2のように混合して組成物を製造した。上記組成物に開始剤を添加した。2,2-ジメトキシ-2-フェニルアセトフェノンを開始剤として使用し、2,2-ジメトキシ-2-フェニルアセトフェノンは混合溶液内にビニル基当量に対して0.5mol%になるように添加した。
第1基板及び第2基板の間に第1スペーサ及び第2スペーサを水平に離隔配置する。ガラス基板を第1及び第2基板として使用した。100μm厚さのポリイミド粘着テープを第1スペーサ及び第2スペーサとして使用した。キャビティが第1ガラス基板及び第2ガラス基板の間に、及び第1スペーサ及び第2スペーサの間に導入される。上記組成物をキャビティに毛細管力を利用して提供した。紫外線を紫外線ランプを使用して窒素気流条件で10分間上記組成物に照射して、UV硬化フィルムを製造した。紫外線ランプは水銀UVHランプを使用し、電力量は1kWであった。組成物層に照射されたランプのUV強度は395~445(UVV)、320~390(UVA)、280~320(UVB)及び250~260(UVC)nmで7.25、8.85、0.26及び0.84mWであった。その後、上記第1及び第2基板を蒸留水に24時間浸漬し、UV-硬化フィルムを第1及び第2基板から除去した後、常温で2時間真空乾燥した。これにより、光透過度調節フィルムを得た。
Claims (17)
- コポリマー及び前記コポリマーにグラフトされたポリマー鎖を含むマトリックス部分と、
第1モノマーから誘導されたポリマーと
を含み、
前記マトリックス部分内に提供された分散された部分を含むが、前記ポリマー鎖は前記第1モノマーから誘導され、
外力が加わる間、第1光透過度を示し、
前記外力が除去されると、前記第1光透過度より大きい第2光透過度を示す
ことを特徴とする、光透過度調節フィルム。 - 前記第2光透過度は、可視領域の光に対する透過度が35%~95%であることを特徴とする、請求項1に記載の光透過度調節フィルム。
- 前記外力が加わる間、前記分散された部分及び前記マトリックス部分の間に空隙が提供され、
前記外力が除去されると、前記空隙が無くなる
ことを特徴とする、請求項1に記載の光透過度調節フィルム。 - 前記分散された部分は、前記マトリックス部分より大きな初期弾性係数を有することを特徴とする、請求項1に記載の光透過度調節フィルム。
- 前記分散された部分は、前記マトリックス部分の100倍~100,000倍の初期弾性係数を有することを特徴とする、請求項4に記載の光透過度調節フィルム。
- 前記マトリックス部分の屈折率と前記分散された部分の屈折率の差が5%未満であることを特徴とする、請求項1に記載の光透過度調節フィルム。
- 前記外力は、引張力を含むことを特徴とする、請求項1に記載の光透過度調節フィルム。
- 前記マトリックス部分は、下記化学式6Aで表されることを特徴とする、請求項8に記載の光透過度調節フィルム。
- 第1モノマーと、
第2モノマーから誘導された第1ポリマー及び第3モノマーから誘導された第2ポリマーを含むコポリマーを含み、
前記コポリマー内の第1ポリマー及び前記第1モノマーのモル比は、1:5~1:100であり、
前記コポリマー内の前記第1ポリマー及び前記第2ポリマーのモル比は、1:4~1:200である
ことを特徴とする、光透過度調節フィルム組成物。 - 前記第1ポリマーは、化学式2Aで表される重合ユニットを含むことを特徴とする、請求項11に記載の光透過度調節フィルム組成物。
- 前記コポリマー内に含まれたビニル基の総モル量に対して前記t-ブチルアクリレートのモル比は、1:5~1:100であることを特徴とする、請求項14に記載の光透過度調節フィルム組成物。
- 重合開始剤をさらに含むことを特徴とする、請求項10に記載の光透過度調節フィルム組成物。
- 前記第1モノマー及び前記コポリマーのうち少なくとも1つはビニル基を含み、
前記重合開始剤はビニル基の総計に対して0.05~5mol%である
ことを特徴とする、請求項16に記載の光透過度調節フィルム組成物。
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