JP6010108B2 - トリアジン系紫外線吸収剤を含むフィルム - Google Patents
トリアジン系紫外線吸収剤を含むフィルム Download PDFInfo
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- JP6010108B2 JP6010108B2 JP2014502827A JP2014502827A JP6010108B2 JP 6010108 B2 JP6010108 B2 JP 6010108B2 JP 2014502827 A JP2014502827 A JP 2014502827A JP 2014502827 A JP2014502827 A JP 2014502827A JP 6010108 B2 JP6010108 B2 JP 6010108B2
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- body layer
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- retroreflective
- film
- triazine
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- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 title claims description 30
- 239000006096 absorbing agent Substances 0.000 title claims description 12
- 239000000463 material Substances 0.000 claims description 26
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 11
- 239000012964 benzotriazole Substances 0.000 claims description 11
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 10
- 239000012965 benzophenone Substances 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims 1
- 238000007789 sealing Methods 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 230000005540 biological transmission Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 230000004927 fusion Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- PICUKNSNSRVIDY-UHFFFAOYSA-N 2h-benzotriazole;diphenylmethanone Chemical compound C1=CC=C2NN=NC2=C1.C=1C=CC=CC=1C(=O)C1=CC=CC=C1 PICUKNSNSRVIDY-UHFFFAOYSA-N 0.000 description 2
- 0 Cc(cc1)cc(*)c1-c1nc(-c(ccc(O*)c2)c2O)nc(-c2ccc(*)cc2*)n1 Chemical compound Cc(cc1)cc(*)c1-c1nc(-c(ccc(O*)c2)c2O)nc(-c2ccc(*)cc2*)n1 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 238000004049 embossing Methods 0.000 description 2
- 229920001903 high density polyethylene Polymers 0.000 description 2
- 239000004700 high-density polyethylene Substances 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 1
- -1 polyethylene terephthalate Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000003981 vehicle 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
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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
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/04—Homopolymers or copolymers of ethene
- C08L23/08—Copolymers of ethene
- C08L23/0846—Copolymers of ethene with unsaturated hydrocarbons containing other atoms than carbon or hydrogen atoms
- C08L23/0869—Acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
-
- G—PHYSICS
- G02—OPTICS
- 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
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/12—Reflex reflectors
- G02B5/122—Reflex reflectors cube corner, trihedral or triple reflector type
- G02B5/124—Reflex reflectors cube corner, trihedral or triple reflector type plural reflecting elements forming part of a unitary plate or sheet
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/208—Filters for use with infrared or ultraviolet radiation, e.g. for separating visible light from infrared and/or ultraviolet radiation
-
- 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
- C08J2323/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
- C08J2323/02—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment
- C08J2323/04—Homopolymers or copolymers of ethene
- C08J2323/08—Copolymers of ethene
-
- 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
- C08J2333/00—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 only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2333/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
-
- 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
- C08K2201/00—Specific properties of additives
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Toxicology (AREA)
- Materials Engineering (AREA)
- Optical Elements Other Than Lenses (AREA)
- Laminated Bodies (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Description
再帰反射率(RA):再帰反射RA(再帰反射率)の係数をASTM E−810−03「Test Method for Coefficient of Retroreflection of Retroreflective Sheeting Utilizing the Coplanar Geometry」に概述されている手順に従って測定した。RAを離散した観察角度で測定し、2つの隣接する測定観察角度の間の環状領域にわたって平均化した。
(1)本体層を準備すること;(2)参照により本明細書に組み込まれている米国特許第5,691,846号(Benson)に記述されているように、キューブコーナー微小構造体を本体層上にキャストすることにより再帰反射性層を作製すること;及び(3)多層封止フィルムをキューブコーナー微小構造体に積層することにより、再帰反射性フィルムを作製した。
比較用本体層Aを用いて再帰反射性フィルムを上述のように作製した。
本体層1を用いて再帰反射性フィルムを上述のように作製した。
以下に、本願発明に関連する発明の実施形態について列挙する。
[実施形態1]
ポリ(エチレン−コ−アクリル酸)と、
トリアジン系UVAと、
を含む、フィルム。
[実施形態2]
ベンゾトリアゾール系UVA及びベンゾフェノン系UVAのうちの少なくとも1つを更に含む、実施形態1に記載のフィルム。
[実施形態3]
約20マイクロメートル〜約1,000マイクロメートルの厚さを有する、実施形態1に記載のフィルム。
[実施形態4]
約1.3ミル(33.0マイクロメートル)〜約4ミル(101.6マイクロメートル)の厚さを有する、実施形態3に記載のフィルム。
[実施形態5]
前記トリアジン系UVAが約350超の分子量を有する、実施形態1に記載のフィルム。
[実施形態6]
前記トリアジン系UVAが、1つ又は2つ以上のかさ高の側鎖基を有する、実施形態1に記載のフィルム。
[実施形態7]
前記フィルムに隣接して配置された再帰反射性シート材を更に含む、実施形態1に記載のフィルム。
[実施形態8]
前記再帰反射性シート材がプリズム状である、実施形態1に記載のフィルム。
[実施形態9]
前記シート材が、前記フィルムに隣接して配置されるとき、ASTM−G−152−06の暴露試験サイクル1a及びASTM G−155−05aの暴露試験サイクル1からなる群から選択される暴露試験サイクルに1500時間かけられた後、0.5度未満の観測角で約50%超の再帰反射保持率を有する、実施形態1に記載のフィルム。
[実施形態10]
再帰反射性シート材であって、
複数のキューブコーナー要素と、
前記キューブコーナー要素に隣接する本体層であって、ポリ(エチレン−コ−アクリル酸)及びトリアジン系UVAを含む前記本体層と、
を含む、再帰反射性シート材。
[実施形態11]
前記キューブコーナー要素と前記本体層との間に、ランド層を更に含む、実施形態10に記載の再帰反射性シート材。
[実施形態12]
前記本体層が、ベンゾトリアゾール系UVA及びベンゾフェノン系UVAのうちの少なくとも1つを更に含む、実施形態10に記載の再帰反射性シート材。
[実施形態13]
前記本体層が、約20マイクロメートル〜約1,000マイクロメートルの厚さを有する、実施形態10に記載の再帰反射性シート材。
[実施形態14]
前記本体層が、約1.3ミル(33.0マイクロメートル)〜約4ミル(101.6マイクロメートル)の厚さを有する、実施形態10に記載の再帰反射性シート材。
[実施形態15]
前記トリアジン系UVAが、約350〜約650の分子量を有する、実施形態10に記載の再帰反射性シート材。
[実施形態16]
前記トリアジン系UVAが1つ又は2つ以上のかさ高の側鎖基を有する、実施形態10に記載の再帰反射性シート材。
[実施形態17]
前記シート材が、ASTM−G−152−06の暴露試験サイクル1a及びASTM G−155−05aの暴露試験サイクル1からなる群から選択される暴露試験サイクルに1500時間かけられた後、0.5度未満の観測角で約50%超の再帰反射保持率を有する、実施形態10に記載の再帰反射性シート材。
[実施形態18]
前記再帰反射保持率が0.2度の観測角で約50%超である、実施形態17に記載の再帰反射性シート材。
Claims (2)
- 再帰反射性シート材であって、
複数のキューブコーナー要素と、
前記キューブコーナー要素に隣接する本体層であって、ポリ(エチレン−コ−アクリル酸)と、トリアジン系紫外線吸収剤と、ベンゾトリアゾール系紫外線吸収剤及びベンゾフェノン系紫外線吸収剤のうちの少なくとも1つと、を含み、前記ベンゾトリアゾール系紫外線吸収剤が、次の化学式:
R1は、CH 3 又はHのいずれか1つであり、
R2は、CH 3 、H、又はフェニルのいずれか1つであり、
R3は、C 6 H 12 、C 8 H 17 、
を含むトリアジン系紫外線吸収剤である、前記本体層と、
を含む、再帰反射性シート材。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161470568P | 2011-04-01 | 2011-04-01 | |
US61/470,568 | 2011-04-01 | ||
PCT/US2012/031402 WO2012135595A2 (en) | 2011-04-01 | 2012-03-30 | Films including triazine-based ultraviolet absorbers |
Related Child Applications (1)
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JP2016131367A Division JP6297098B2 (ja) | 2011-04-01 | 2016-07-01 | トリアジン系紫外線吸収剤を含むフィルム |
Publications (3)
Publication Number | Publication Date |
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JP2014511917A JP2014511917A (ja) | 2014-05-19 |
JP2014511917A5 JP2014511917A5 (ja) | 2015-05-14 |
JP6010108B2 true JP6010108B2 (ja) | 2016-10-19 |
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JP2014502827A Active JP6010108B2 (ja) | 2011-04-01 | 2012-03-30 | トリアジン系紫外線吸収剤を含むフィルム |
JP2016131367A Active JP6297098B2 (ja) | 2011-04-01 | 2016-07-01 | トリアジン系紫外線吸収剤を含むフィルム |
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Country Status (6)
Country | Link |
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US (2) | US9658363B2 (ja) |
EP (1) | EP2694573B1 (ja) |
JP (2) | JP6010108B2 (ja) |
KR (1) | KR101882044B1 (ja) |
BR (1) | BR112013025151B1 (ja) |
WO (1) | WO2012135595A2 (ja) |
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KR101882044B1 (ko) * | 2011-04-01 | 2018-07-25 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 트라이아진계 자외선 흡수제를 포함하는 필름 |
CN105474051B (zh) | 2013-08-19 | 2020-09-08 | 3M创新有限公司 | 包括低弹性模量层的回射片材 |
KR102395529B1 (ko) * | 2015-10-22 | 2022-06-02 | 삼성전자주식회사 | 통신 장치, 및 디스플레이 장치 및 그 제어방법 |
US20180059015A1 (en) * | 2016-08-30 | 2018-03-01 | Sensii, Inc. | Personal liquid analysis system |
JP2020519496A (ja) | 2017-05-10 | 2020-07-02 | スリーエム イノベイティブ プロパティズ カンパニー | フルオロポリマー物品及び関連する方法 |
US20200096683A1 (en) | 2017-05-25 | 2020-03-26 | 3M Innovative Properties Company | Cube corner retroreflective articleswith tailored retroreflectivity and methods of making |
KR20200116922A (ko) | 2018-02-05 | 2020-10-13 | 주식회사 쿠라레 | 열가소성 수지 필름, 및 그 제조 방법 |
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BR112013025151B1 (pt) | 2021-09-28 |
EP2694573B1 (en) | 2020-05-27 |
WO2012135595A2 (en) | 2012-10-04 |
WO2012135595A3 (en) | 2013-03-14 |
JP2014511917A (ja) | 2014-05-19 |
EP2694573A4 (en) | 2014-11-26 |
EP2694573A2 (en) | 2014-02-12 |
BR112013025151A2 (pt) | 2020-11-10 |
US20140009824A1 (en) | 2014-01-09 |
US9658363B2 (en) | 2017-05-23 |
US20170254926A1 (en) | 2017-09-07 |
US10598823B2 (en) | 2020-03-24 |
KR101882044B1 (ko) | 2018-07-25 |
JP6297098B2 (ja) | 2018-03-20 |
JP2016186086A (ja) | 2016-10-27 |
KR20140018320A (ko) | 2014-02-12 |
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