JP6688798B2 - 負の光弾性定数を有するポリマー材料 - Google Patents
負の光弾性定数を有するポリマー材料 Download PDFInfo
- Publication number
- JP6688798B2 JP6688798B2 JP2017529060A JP2017529060A JP6688798B2 JP 6688798 B2 JP6688798 B2 JP 6688798B2 JP 2017529060 A JP2017529060 A JP 2017529060A JP 2017529060 A JP2017529060 A JP 2017529060A JP 6688798 B2 JP6688798 B2 JP 6688798B2
- Authority
- JP
- Japan
- Prior art keywords
- doped
- weight
- vinylpyridine
- p2vp
- dopant
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000002861 polymer material Substances 0.000 title 1
- 229920000885 poly(2-vinylpyridine) Polymers 0.000 claims description 27
- 239000002019 doping agent Substances 0.000 claims description 13
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 description 25
- 239000011521 glass Substances 0.000 description 13
- 239000000758 substrate Substances 0.000 description 12
- -1 aliphatic polycyclic compound Chemical class 0.000 description 10
- 239000010408 film Substances 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 238000000576 coating method Methods 0.000 description 7
- 239000004973 liquid crystal related substance Substances 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 6
- 239000004926 polymethyl methacrylate Substances 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- 239000002131 composite material Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 150000003384 small molecules Chemical class 0.000 description 4
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 4
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- FNAWJOBKLWLHTA-UHFFFAOYSA-N [4-(trifluoromethyl)benzoyl] 4-(trifluoromethyl)benzoate Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)OC(=O)C1=CC=C(C(F)(F)F)C=C1 FNAWJOBKLWLHTA-UHFFFAOYSA-N 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229940116333 ethyl lactate Drugs 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- 229920000075 poly(4-vinylpyridine) Polymers 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 238000007764 slot die coating Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N trans-Stilbene Natural products C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- OOIBFPKQHULHSQ-UHFFFAOYSA-N (3-hydroxy-1-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC2(O)CC1(OC(=O)C(=C)C)C3 OOIBFPKQHULHSQ-UHFFFAOYSA-N 0.000 description 1
- PQGPUBAARWWOOP-UHFFFAOYSA-N 2-(3,4,5-trifluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC(F)=C(F)C(F)=C1 PQGPUBAARWWOOP-UHFFFAOYSA-N 0.000 description 1
- DTNSDCJFTHMDAK-UHFFFAOYSA-N 2-cyanobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C#N DTNSDCJFTHMDAK-UHFFFAOYSA-N 0.000 description 1
- FBHXELGUZCMKQY-UHFFFAOYSA-N 2-fluoro-6-phenoxybenzonitrile Chemical compound FC1=CC=CC(OC=2C=CC=CC=2)=C1C#N FBHXELGUZCMKQY-UHFFFAOYSA-N 0.000 description 1
- QMSDNBJQBPHACW-UHFFFAOYSA-N 5-methyl-2-phenylbenzonitrile Chemical compound N#CC1=CC(C)=CC=C1C1=CC=CC=C1 QMSDNBJQBPHACW-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- UBXYXCRCOKCZIT-UHFFFAOYSA-N biphenyl-3-ol Chemical compound OC1=CC=CC(C=2C=CC=CC=2)=C1 UBXYXCRCOKCZIT-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000009749 continuous casting Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000005489 elastic deformation Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229940119545 isobornyl methacrylate Drugs 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000012788 optical film Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
-
- 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
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/095—Carboxylic acids containing halogens
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L39/00—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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
- C08L39/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
- C08L39/08—Homopolymers or copolymers of vinyl-pyridine
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D139/00—Coating compositions based on 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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Coating compositions based on derivatives of such polymers
- C09D139/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
- C09D139/08—Homopolymers or copolymers of vinyl-pyridine
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G02B5/3083—Birefringent or phase retarding elements
-
- 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
- C08J2325/00—Characterised by the use 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 an aromatic carbocyclic ring; Derivatives of such polymers
- C08J2325/18—Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
-
- 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
- C08J2339/00—Characterised by the use 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 single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Derivatives of such polymers
- C08J2339/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
- C08J2339/08—Homopolymers or copolymers of vinyl-pyridine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Optics & Photonics (AREA)
- General Physics & Mathematics (AREA)
- Polarising Elements (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Description
Claims (7)
- 式(I):
式中、R 1 が、水素またはメチルであり、R 2 が、アダマンタン、ビシクロ[2,2,1]アルカン、ビシクロ[2,2,2]アルカン、及びビシクロ[2,1,1]アルカンからなる群から選択されるC 6 −C 20 脂肪族多環式置換基であり、前記C 6 −C 20 脂肪族多環式置換基が置換されていないか、またはメチル基で置換されているドーパントを含む、ドープされたポリ(2−ビニルピリジン)。 - R 2 の前記C6−C20脂肪族多環式置換基が置換されていない、請求項1に記載のドープされたポリ(2−ビニルピリジン)。
- R2が、C7−C15架橋多環式置換基である、請求項1または2に記載のドープされたポリ(2−ビニルピリジン)。
- 10〜27重量%の前記ドーパントを含む、請求項1〜3のいずれか1項に記載のドープされたポリ(2−ビニルピリジン)。
- 7〜30重量%の式(II)のドーパントを含み、
- Gが、フルオロ及びクロロからなる群から選択される1〜3個の置換基を表す、請求項5に記載のドープされたポリ(2−ビニルピリジン)。
- 10〜27重量%の前記ドーパントを含む、請求項6に記載のドープされたポリ(2−ビニルピリジン)。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201462093573P | 2014-12-18 | 2014-12-18 | |
US62/093,573 | 2014-12-18 | ||
PCT/US2015/064205 WO2016099973A1 (en) | 2014-12-18 | 2015-12-07 | Polymeric materials with negative photoelastic constants |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2018500411A JP2018500411A (ja) | 2018-01-11 |
JP6688798B2 true JP6688798B2 (ja) | 2020-04-28 |
Family
ID=55073104
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017529060A Expired - Fee Related JP6688798B2 (ja) | 2014-12-18 | 2015-12-07 | 負の光弾性定数を有するポリマー材料 |
Country Status (6)
Country | Link |
---|---|
US (1) | US20170362409A1 (ja) |
EP (1) | EP3233998B1 (ja) |
JP (1) | JP6688798B2 (ja) |
KR (1) | KR20170097062A (ja) |
CN (1) | CN107003460A (ja) |
WO (1) | WO2016099973A1 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR200487277Y1 (ko) | 2018-01-16 | 2018-08-30 | 유선옥 | 기능성 장신구 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW200506467A (en) * | 2002-12-19 | 2005-02-16 | Nitto Denko Corp | Birefringent optical film, elliptically polarizing plate using the same, and liquid crystal |
US20060074161A1 (en) * | 2004-09-28 | 2006-04-06 | Shi-Jun Yang | Stabilized UV transparent acrylic composition |
CN101467079B (zh) * | 2006-11-08 | 2011-03-23 | Dic株式会社 | 光取向膜用组合物、光取向膜和光学异构体 |
JP5463914B2 (ja) * | 2008-01-30 | 2014-04-09 | コニカミノルタ株式会社 | アクリル樹脂含有フィルム、それを用いた偏光板及び液晶表示装置 |
JP2009235212A (ja) * | 2008-03-26 | 2009-10-15 | Fujifilm Corp | セルロース体組成物、セルロース体フィルム、光学補償フィルム、偏光板および画像表示装置 |
US20140054515A1 (en) * | 2011-02-28 | 2014-02-27 | Nthdegree Technologies Worldwide Inc. | Metallic Nanowire Ink Composition for a Substantially Transparent Conductor |
CN105102534B (zh) * | 2013-04-05 | 2019-08-23 | 株式会社钟化 | 树脂组合物及其膜 |
CN104183736A (zh) * | 2013-05-23 | 2014-12-03 | 海洋王照明科技股份有限公司 | 有机电致发光器件及其制备方法 |
KR20170095898A (ko) * | 2014-12-18 | 2017-08-23 | 롬 앤드 하스 일렉트로닉 머트어리얼즈 엘엘씨 | 음의 광탄성 상수를 갖는 중합체 물질 |
-
2015
- 2015-12-07 KR KR1020177017776A patent/KR20170097062A/ko unknown
- 2015-12-07 US US15/534,748 patent/US20170362409A1/en not_active Abandoned
- 2015-12-07 WO PCT/US2015/064205 patent/WO2016099973A1/en active Application Filing
- 2015-12-07 EP EP15820924.7A patent/EP3233998B1/en not_active Not-in-force
- 2015-12-07 JP JP2017529060A patent/JP6688798B2/ja not_active Expired - Fee Related
- 2015-12-07 CN CN201580064730.0A patent/CN107003460A/zh active Pending
Also Published As
Publication number | Publication date |
---|---|
US20170362409A1 (en) | 2017-12-21 |
KR20170097062A (ko) | 2017-08-25 |
WO2016099973A1 (en) | 2016-06-23 |
EP3233998B1 (en) | 2019-01-30 |
EP3233998A1 (en) | 2017-10-25 |
JP2018500411A (ja) | 2018-01-11 |
CN107003460A (zh) | 2017-08-01 |
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