JP2567238B2 - Resin plate for light collection - Google Patents

Resin plate for light collection

Info

Publication number
JP2567238B2
JP2567238B2 JP62068791A JP6879187A JP2567238B2 JP 2567238 B2 JP2567238 B2 JP 2567238B2 JP 62068791 A JP62068791 A JP 62068791A JP 6879187 A JP6879187 A JP 6879187A JP 2567238 B2 JP2567238 B2 JP 2567238B2
Authority
JP
Japan
Prior art keywords
light
resin plate
plate
resin
present
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
Application number
JP62068791A
Other languages
Japanese (ja)
Other versions
JPS63235370A (en
Inventor
行雄 石坂
達也 沼
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nippon Kayaku Co Ltd
Original Assignee
Nippon Kayaku Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nippon Kayaku Co Ltd filed Critical Nippon Kayaku Co Ltd
Priority to JP62068791A priority Critical patent/JP2567238B2/en
Publication of JPS63235370A publication Critical patent/JPS63235370A/en
Application granted granted Critical
Publication of JP2567238B2 publication Critical patent/JP2567238B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Description

【発明の詳細な説明】 産業上の利用分野 本発明は集光用樹脂板に関する。更に詳しくはスクア
リリウム化合物を用いた樹脂製集光板(又は集光シー
ト)に関する。
TECHNICAL FIELD The present invention relates to a light-collecting resin plate. More specifically, the present invention relates to a resin light collecting plate (or light collecting sheet) using a squarylium compound.

従来の技術 従来クマリン系色素、ナフタル酸系色素、キノフタロ
ン系色素、ローダミン系色素、チオキサンテン系色素、
ベンゾピラン系色素、チオインジゴ系色素、ペリレン系
色素等の色素を用いて、集光させる方法は公知である。
(特開昭56−120736,57−125260,58−40359,58−11188
6,60−39485,60−203650)しかし、これらの色素は600n
m未満の光を吸収し600nmの光を放射する性質にすぐれて
いるというものの600nm以上の光を吸収し吸収光より長
波長の光を放出するというような性能については十分で
ない。
Conventional technology Conventional coumarin dyes, naphthalic acid dyes, quinophthalone dyes, rhodamine dyes, thioxanthene dyes,
A method of collecting light using a dye such as a benzopyran dye, a thioindigo dye, and a perylene dye is known.
(JP-A-56-120736, 57-125260, 58-40359, 58-11188
6,60-39485,60-203650) but these dyes
It excels in the property of absorbing light of less than m and emitting light of 600 nm, but it is not sufficient in the performance of absorbing light of 600 nm or more and emitting light of a longer wavelength than the absorbed light.

発明が解決しようとする問題点 600nm以上の光を吸収し、吸収光より長波長の光を効
率よく放出する性能にすぐれ、かつ耐光性の十分な化合
物が望まれている。
Problems to be Solved by the Invention There is a demand for a compound that has excellent light-absorbing properties and is capable of absorbing light having a wavelength of 600 nm or more and efficiently emitting light having a wavelength longer than the absorbed light.

問題点を解決する為の手段 本発明者等は、前記したような問題点を解決すべく鋭
意検討努力した結果、本発明に至った。即ち本発明は樹
脂中にスクアリリウム化合物が均質に分散されているこ
とを特徴とする集光用樹脂板又はシートを提供する。
Means for Solving the Problems The inventors of the present invention have achieved the present invention as a result of intensive studies and efforts to solve the above problems. That is, the present invention provides a light-collecting resin plate or sheet in which a squarylium compound is uniformly dispersed in a resin.

本発明の集光用樹脂板に用いられるスクアリリウム化
合物の例としては例えば次の化合物があげられ
る。(()はλmax(nm)を測定したときの溶媒を示
す。) 本発明で使用し得る上記のスクアリリウム化合物は公
知であり例えばAngew.Chem.internat.Edit.Vol7(196
8)p.530〜535に記載された方法に準じて製造すること
が出来る。
Examples of the squarylium compound used for the light collecting resin plate of the present invention include the following compounds. (() Indicates the solvent when λmax (nm) was measured.) The above-mentioned squarylium compounds that can be used in the present invention are known and, for example, Angew.Chem.internat.Edit.Vol7 (196
8) It can be manufactured according to the method described in p.530-535.

本発明の集光用樹脂板を製造するために適した樹脂の
例としてはポリメチルメタアクリレート、ポリメチルア
クリレート、ポリスチロール、ポリジエチレングリコー
ルジアリルビスーカーボネートポリアミド、ポリエステ
ル、ポリカーボネートならびにポリ塩化ビニル等が挙げ
られる。
Examples of resins suitable for producing the light-collecting resin plate of the present invention include polymethylmethacrylate, polymethylacrylate, polystyrene, polydiethylene glycol diallyl bis-carbonate polyamide, polyester, polycarbonate and polyvinyl chloride. .

これらの樹脂から本発明の集光用樹脂板を製造する方
法としては例えば前記した樹脂をペレット状又は粉状に
加工しこれに前記したようなスクアリリウム化合物を通
常0.001〜5%より好ましくは0.003〜2%(重量比)添
加し必要に応じ加熱溶融し熱時噴射し、粒状化したのち
使用した樹脂に応じた射出温度で板状又はシート状に成
型する。板、シートの厚さは任意に選べばよいが通常は
厚さ0.5〜100mm(板)、0.01〜0.5mm(シート)であ
る。
As a method for producing the light-collecting resin plate of the present invention from these resins, for example, the above-mentioned resin is processed into a pellet form or a powder form, and the squarylium compound as described above is usually added in an amount of 0.001 to 5%, preferably 0.003 to 2% (weight ratio) is added, and if necessary, heated and melted, jetted while hot, granulated, and then molded into a plate or sheet at an injection temperature according to the resin used. The thickness of the plate or sheet may be arbitrarily selected, but the thickness is usually 0.5 to 100 mm (plate) and 0.01 to 0.5 mm (sheet).

又本発明の集光用樹脂板を得るには次のようにしても
よい。即ち前記した樹脂のモノマーに前記したようなス
クアリリウム化合物を添加しておき重合と同時に成型し
たり、あるいは前記したような樹脂を例えばクロロホル
ム、クロルベンゼン、トルエン、キシレン、アセトン、
メチルエチルケトン、テトラヒドロフラン、ジメチルホ
ルマミド、N−メチルピロリドン、メタノール、エタノ
ール、エチレングリコール、酢酸エチル、酢酸ブチルの
ような有機溶剤に溶解してこれに前記したようなスクア
リリウム化合物を添加し次いで型に流し込み有機溶剤を
気化させるというような方法も採用出来る。
Further, the following may be performed to obtain the light collecting resin plate of the present invention. That is, the squarylium compound as described above is added to the monomer of the resin described above and molded at the same time as the polymerization, or the resin as described above is formed by, for example, chloroform, chlorobenzene, toluene, xylene, acetone,
It is dissolved in an organic solvent such as methyl ethyl ketone, tetrahydrofuran, dimethylformamide, N-methylpyrrolidone, methanol, ethanol, ethylene glycol, ethyl acetate or butyl acetate, and the squarylium compound as described above is added thereto and then poured into a mold. A method of vaporizing the solvent can also be adopted.

本発明で使用するスクアリリウム化合物は本発明の集
光用樹脂板中において表面から600nm以上の光線(直線
光及び拡散光)を捕らえ、これをより長波長側にシフト
せしめた上で放出(放射)する。放出された光は樹脂板
内でその大部分が全反射の法則に従って板又はシートの
エッジ部分へ誘導され、そこで濃密化された状態で樹脂
板外に放出される。
The squarylium compound used in the present invention captures a light ray of 600 nm or more (straight line light and diffused light) from the surface in the light-collecting resin plate of the present invention, and shifts this to a longer wavelength side and then emits it (radiation). To do. Most of the emitted light is guided to the edge portion of the plate or sheet according to the law of total reflection inside the resin plate, and is emitted outside the resin plate in a dense state there.

この集光用樹脂板の用途としては次のものがある。即
ち集光用樹脂板のエッジの一箇所あるいは数箇所に太陽
電池を取り付け、それ以外のエッジ部分には、そこに達
した光の向きを太陽電池の方へ変える為に銀メッキ等を
施しておきエッジから出てくる螢光を電気エネルギーに
変えることができる。このエネルギー変換を効率よく行
うためには太陽光をできるだけ多く吸収する色素が望ま
しいのであるが、太陽光の全波長において吸収を示す色
素は存在せず個々のスペクトル領域に其々異種の色素を
含有した樹脂板をかさね合わせて使用することになる。
即ち最上段樹脂板中の色素が短波長の光を、最下段の樹
脂板中の色素が長波長の光を吸収するという様に組み合
わせることにより、広範囲の太陽光線を吸収することが
できる。ここにおいて600nm未満の光線を吸収させるた
めには例えば公知のクマリン系、ナフタル酸、キノフタ
ロン系、チオキサンテン系、ペリレン系、チオインジゴ
系色素等を含有した樹脂板等が、又600nm以上の光線を
吸収するためには本発明の樹脂板が用いられる。
The applications of this light collecting resin plate are as follows. That is, a solar cell is attached to one or several points on the edge of the light-collecting resin plate, and silver plating is applied to the other edge to change the direction of the light reaching it toward the solar cell. Fluorescence emitted from the edge can be converted into electric energy. In order to perform this energy conversion efficiently, it is desirable to use a dye that absorbs as much sunlight as possible, but there is no dye that absorbs at all wavelengths of sunlight, and each spectral region contains different dyes. The resin plates will be used together.
That is, a wide range of sun rays can be absorbed by combining the dyes in the uppermost resin plate with the light of short wavelength and the dyes in the resin plate of the lowermost layer with the light of long wavelength. Here, in order to absorb a light ray of less than 600 nm, for example, a resin plate containing a known coumarin-based, naphthalic acid, quinophthalone-based, thioxanthene-based, perylene-based, thioindigo-based dye, etc., also absorbs a light of 600 nm or more. In order to do so, the resin plate of the present invention is used.

本発明の集光用樹脂板は前記したような太陽電池の
他、シンチレーター、エネルギー消費の少ない情報装置
としての電気的制御装置と組み合わせるのに適し、又発
光製図機器、間接照明更に信号、標識、警告等を目的と
する受光タイプの掲示エレメント、半導体レーザーLED
等の光を集光し受光素子へ導く装置等に使用可能であ
る。
The condensing resin plate of the present invention is suitable for combination with a solar cell as described above, a scintillator, an electric control device as an information device with low energy consumption, a light emission drafting device, an indirect illumination signal, a sign, Light-receiving type of posting element for the purpose of warning, semiconductor laser LED
It can be used in a device or the like that collects light such as light and guides it to a light receiving element.

実施例 以下実施例により本発明を具体的に説明する。実施例
中「部」は特に限定しない限り重量部を示す。
Examples Hereinafter, the present invention will be described specifically with reference to examples. In the examples, “parts” means parts by weight unless otherwise specified.

実施例1. 次式の化合物 0.3部をPMMA1000部のペレットに混合し250℃の射出温
度で成型し厚さ2mmの樹脂板65×90の大きさにカットし
た。この樹脂板は642nmで吸収極大値を、650nmで放射極
大値を示した。吸収された光は樹脂板の周辺部に集光さ
れていた。
Example 1. Compound of formula 0.3 parts of PMMA was mixed with 1000 parts of PMMA pellets, molded at an injection temperature of 250 ° C., and cut into a resin plate having a thickness of 2 mm and a size of 65 × 90. This resin plate showed an absorption maximum at 642 nm and an emission maximum at 650 nm. The absorbed light was condensed on the periphery of the resin plate.

実施例2. 次式の化合物 0.01部をポリスチロールブロック重合物の粉砕物100
部に乾式で混合する。混合物をシリンダー温度220℃で
スクリュー式押出機により溶融し、均質化する。可塑性
のある着色物をノズル孔から熱時噴射し、糸状で引出す
ことにより粒状化する。こうして得られた粒状物を射出
成形装置により220℃で射出成形して成形品とし、ある
いは圧縮成形機により任意の成形品に圧縮成形する。青
色のプレス成形体が得られ、これらの成形体はλmax632
mμの光を吸収λmax635nmの光を発し、良好な光堅牢性
を示した。
Example 2. Compound of formula 0.01 part of pulverized polystyrene block polymer 100
Dry mix. The mixture is melted and homogenized in a screw extruder at a cylinder temperature of 220 ° C. The plastic coloring matter is sprayed from the nozzle hole at the time of heat and drawn out in the form of a thread to be granulated. The granular material thus obtained is injection-molded by an injection molding device at 220 ° C. to obtain a molded product, or a compression molding machine is compression-molded into an arbitrary molded product. Blue press-molded products are obtained, and these molded products have λmax632
It absorbs mμ of light and emits light of λmax 635nm, showing good light fastness.

実施例3. 溶融ポリメチルメタクリレートに実施例2で用いたス
クアリリウム化合物をポリメチルメタクリレートに対し
0.01%添加し、均質に分散させ、厚さ1mmの板状に加工
した。この樹脂板は、λmax633nmの光を吸収しλmax636
nmの光を放出した。
Example 3. The fused squarylium compound used in Example 2 was added to molten polymethylmethacrylate to polymethylmethacrylate.
0.01% was added and dispersed uniformly, and processed into a plate with a thickness of 1 mm. This resin plate absorbs light of λmax 633 nm and absorbs λmax 636 nm.
emitted light of nm.

実施例4. 高速混合機により下記化合物 0.05部とポリスチロールブロック重合物の粒砕物100
部を乾式で混合した。この混合物をシリンダー温度200
〜250℃でスクリュー式押出し機により溶融し、均質化
した。可塑性ある着色物をノズル孔から熱時噴射するこ
とにより粒状化した。次いで射出成形装置により220℃
で射出成形して厚さ2.5mmの板状の成形品とした。
Example 4. High speed mixer Granules of 0.05 parts and polystyrene block polymer 100
The parts were dry mixed. Add this mixture to a cylinder temperature of 200
Melted and homogenized in a screw extruder at ~ 250 ° C. The plastic colored material was granulated by being hot jetted from a nozzle hole. 220 ℃ by injection molding machine
Was injection-molded into a plate-shaped molded product having a thickness of 2.5 mm.

この板状の成形体は、λmax730nmの光を吸収し板のエ
ッジより735nmの光を放射した。
This plate-shaped molded body absorbed light of λmax 730 nm and emitted light of 735 nm from the edge of the plate.

実施例5. 下記化合物 0.05部とポリカーボネート樹脂ペレット100部を乾式
で混合した。混合物をシリンダー温度270〜300℃でスク
リュー式押出機により溶融し、均質化した。可塑性ある
着色物をノズル孔から熱時噴射して粒状にする。こうし
て得られた粒状物を次いで射出成形装置により270〜300
℃で射出成形して厚さ3mmの板状の成形品に成形した。
このものは、λmax643nmの光を吸収し板の側面(エッジ
部分)よりλmax653nmの光を放射した。
Example 5. The following compound 0.05 part and 100 parts of polycarbonate resin pellets were dry mixed. The mixture was melted and homogenized in a screw extruder at a cylinder temperature of 270-300 ° C. The plastic coloring matter is sprayed from the nozzle holes at the time of heat to form particles. The granules thus obtained are then 270-300 in an injection molding machine.
Injection molding was carried out at ℃ and molded into a plate-shaped molded product having a thickness of 3 mm.
This product absorbed light of λmax643nm and emitted light of λmax653nm from the side surface (edge portion) of the plate.

実施例6. 下記化合物 0.01部とポリメチルメタアクリレート1000部を熱時混
合し、厚さ1.5mmの板状に加工した。この板は727nm(吸
収極大値)の光を吸収し733nm(放射極大値)の光をエ
ッジ部分から放射した。
Example 6. The following compound 0.01 part and 1000 parts of polymethylmethacrylate were mixed under heat and processed into a plate having a thickness of 1.5 mm. This plate absorbed light at 727 nm (absorption maximum) and emitted light at 733 nm (radiation maximum) from the edge.

発明の効果 波長600nm以上の光線を吸収し、吸収した光線の波長
より長波長側の光線を効率よく放出し、かつ放出された
光線の濃密化のすぐれた集光用樹脂板が得られた。
Effects of the Invention A light-collecting resin plate that absorbs light having a wavelength of 600 nm or more, efficiently emits light having a wavelength longer than the wavelength of the absorbed light, and is excellent in the density of the emitted light is obtained.

Claims (1)

(57)【特許請求の範囲】(57) [Claims] 【請求項1】樹脂中にスクアリリウム化合物が均質に分
散されていることを特徴とする集光用樹脂板又はシート
1. A light collecting resin plate or sheet in which a squarylium compound is uniformly dispersed in a resin.
JP62068791A 1987-03-25 1987-03-25 Resin plate for light collection Expired - Fee Related JP2567238B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP62068791A JP2567238B2 (en) 1987-03-25 1987-03-25 Resin plate for light collection

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP62068791A JP2567238B2 (en) 1987-03-25 1987-03-25 Resin plate for light collection

Publications (2)

Publication Number Publication Date
JPS63235370A JPS63235370A (en) 1988-09-30
JP2567238B2 true JP2567238B2 (en) 1996-12-25

Family

ID=13383895

Family Applications (1)

Application Number Title Priority Date Filing Date
JP62068791A Expired - Fee Related JP2567238B2 (en) 1987-03-25 1987-03-25 Resin plate for light collection

Country Status (1)

Country Link
JP (1) JP2567238B2 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996009289A1 (en) * 1994-09-21 1996-03-28 Kyowa Hakko Kogyo Co., Ltd. Photopolymerizable composition containing squarylium compound
JP5147032B2 (en) * 2001-04-03 2013-02-20 株式会社林原 Cyanine dye
DE60107465D1 (en) * 2001-10-23 2004-12-30 Council Scient Ind Res DYES OF SQUARAINE TYPE AND A METHOD FOR THE PRODUCTION THEREOF
TW200626701A (en) * 2004-11-12 2006-08-01 Hirose Engineering Co Ltd Plastic molded product and method for predicting the wavelength of the illuminating light
EP2673321A2 (en) * 2011-02-09 2013-12-18 Stephen R. Forrest Organic photosensitive devices comprising aryl squaraines and methods of making the same
JP6797298B2 (en) * 2017-06-08 2020-12-09 富士フイルム株式会社 Method for manufacturing a resin molded product of a resin kneaded product and a resin molded product of a resin kneaded product
JP7011708B2 (en) * 2018-04-11 2022-02-10 富士フイルム株式会社 Dye filter, backlight unit and liquid crystal display device

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61218550A (en) * 1985-03-23 1986-09-29 Mitsubishi Chem Ind Ltd Squarylium compound
JPS62432A (en) * 1985-06-27 1987-01-06 Mitsubishi Chem Ind Ltd Squarylium compound
JPS61260038A (en) * 1985-05-15 1986-11-18 Mitsubishi Chem Ind Ltd Squarylium compound

Also Published As

Publication number Publication date
JPS63235370A (en) 1988-09-30

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