JPH04317025A - Light control material and light control element containing this material - Google Patents
Light control material and light control element containing this materialInfo
- Publication number
- JPH04317025A JPH04317025A JP8516991A JP8516991A JPH04317025A JP H04317025 A JPH04317025 A JP H04317025A JP 8516991 A JP8516991 A JP 8516991A JP 8516991 A JP8516991 A JP 8516991A JP H04317025 A JPH04317025 A JP H04317025A
- Authority
- JP
- Japan
- Prior art keywords
- light control
- group
- compd
- formula
- liquid crystal
- 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.)
- Pending
Links
- 239000000463 material Substances 0.000 title claims abstract description 21
- 229920000642 polymer Polymers 0.000 claims abstract description 24
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 23
- 230000005684 electric field Effects 0.000 claims abstract description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 4
- -1 tetrahydrofurfuryl Chemical group 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000000758 substrate Substances 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 8
- 230000005540 biological transmission Effects 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000002834 transmittance Methods 0.000 abstract description 13
- 239000004988 Nematic liquid crystal Substances 0.000 abstract description 8
- 230000004044 response Effects 0.000 abstract description 7
- 125000004386 diacrylate group Chemical group 0.000 abstract description 6
- 230000035945 sensitivity Effects 0.000 abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 230000003252 repetitive effect Effects 0.000 abstract 1
- 230000004043 responsiveness Effects 0.000 abstract 1
- 238000000411 transmission spectrum Methods 0.000 description 6
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 4
- 239000004990 Smectic liquid crystal Substances 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000654 additive Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 230000003098 cholesteric effect Effects 0.000 description 2
- 229940125890 compound Ia Drugs 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 229930192419 itoside Natural products 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- DTGKSKDOIYIVQL-NQMVMOMDSA-N (+)-Borneol Natural products C1C[C@]2(C)[C@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-NQMVMOMDSA-N 0.000 description 1
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001344 alkene derivatives Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- NEHNMFOYXAPHSD-UHFFFAOYSA-N beta-citronellal Natural products O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000002704 decyl group Chemical group [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])* 0.000 description 1
- MYRTYDVEIRVNKP-UHFFFAOYSA-N divinylbenzene Substances C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000001400 nonyl 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])[H] 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
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Landscapes
- Liquid Crystal (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は、調光材料及びそれを含
む調光素子に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a light control material and a light control element containing the same.
【０００２】0002
【従来の技術】液晶とそれを保持する高分子よりなる調
光材料は、電界無印加時には、高分子の屈折率と液晶の
屈折率との差等により入射光が散乱するため、液晶層は
くもり状態となり、一方、電界が印加されると、液晶が
その電場方向に向って整列することから、高分子の屈折
率と液晶の屈折率とが、近い値となるため、透明状態に
なる。そして、電界を外すと再び元のくもり状態となる
。[Prior Art] When no electric field is applied to a light control material made of a liquid crystal and a polymer holding it, incident light is scattered due to the difference between the refractive index of the polymer and the refractive index of the liquid crystal. On the other hand, when an electric field is applied, the liquid crystals align in the direction of the electric field, and the refractive index of the polymer and the liquid crystal become close to each other, resulting in a transparent state. Then, when the electric field is removed, the cloudy state returns to its original state.
【０００３】従来、この様な性質を利用した調光素子が
、例えば、特開昭６４−６２６１５号、特公表２−５０
２９２９号、特開平１−３１２５２７号等に開示されて
いる。Conventionally, light control elements utilizing such properties have been disclosed, for example, in Japanese Patent Application Laid-open No. 64-62615 and Japanese Patent Publication No. 2-50.
No. 2929, Japanese Unexamined Patent Publication No. 1-312527, etc.
【０００４】0004
【発明が解決しようとする課題】調光素子には、任意の
透過率、繰り返し応答性、電圧感受性、応答速度、膜の
均一性、耐光性、耐熱性、耐水性等の耐久性等が要求さ
れるが、上記従来の技術は、いずれもこれらの要求特性
を満足し得るものとは言えなかった。特に、特開平１−
３１２５２７号で得られた調光素子はメモリー性を有す
ることを目的とした非可逆的なものであり、繰り返し応
答可能な調光素子とは異なるものである。[Problems to be solved by the invention] Light control elements are required to have arbitrary transmittance, repeated response, voltage sensitivity, response speed, film uniformity, and durability such as light resistance, heat resistance, and water resistance. However, none of the above conventional techniques can satisfy these required characteristics. In particular, JP-A-1-
The light control device obtained in No. 312527 is an irreversible device intended to have memory properties, and is different from a light control device that can respond repeatedly.
【０００５】本発明は上記従来の問題点を解決し、調光
素子に要求される特性、即ち、任意の透過率、繰り返し
応答性、電圧感受性、応答速度、膜の均一性、耐光性、
耐熱性、耐水性等の耐久性等を、十分に満足することが
できる高特性調光材料及びそれを含む調光素子を提供す
ることを目的とする。The present invention solves the above-mentioned conventional problems and satisfies the characteristics required of a light control element, namely, arbitrary transmittance, repeated response, voltage sensitivity, response speed, film uniformity, light resistance,
It is an object of the present invention to provide a high-performance light control material that can sufficiently satisfy durability such as heat resistance and water resistance, and a light control element containing the same.
【０００６】[0006]
【課題を解決するための手段】請求項１の調光材料は、
液晶及び高分子を含んで成り、電界の印加の有無により
、光の透過散乱を制御する調光材料において、前記高分
子が、一般式（Ｉ）[Means for solving the problem] The light control material according to claim 1 has the following features:
A light control material comprising a liquid crystal and a polymer and controlling transmission and scattering of light depending on the presence or absence of an electric field, wherein the polymer is represented by the general formula (I).
【０００７】[0007]
【化３】[C3]
【０００８】（式中、Ｒは水素原子又はメチル基を示し
、ｎは１〜２５の整数を示す。）で示されるジアクリレ
ート系化合物及び一般式（ＩＩ）(In the formula, R represents a hydrogen atom or a methyl group, and n represents an integer of 1 to 25.) Diacrylate compounds represented by the general formula (II)
【０００９】[0009]
【化４】[C4]
【００１０】（式中、Ｒ１は水素原子又はメチル基を示
し、Ｒ２は炭素数１〜１８のアルキル基、シクロヘキシ
ル基又はテトラヒドロフルフリル基を示す。）で示され
るモノアクリレート系化合物から成る重合性組成物を共
重合させて得られる高分子であることを特徴とする。(In the formula, R1 represents a hydrogen atom or a methyl group, and R2 represents an alkyl group having 1 to 18 carbon atoms, a cyclohexyl group, or a tetrahydrofurfuryl group.) It is characterized by being a polymer obtained by copolymerizing a composition.
【００１１】請求項２の調光素子は、少くとも一方が透
明な、内面に電極を有する一対の基板間に請求項１に記
載の調光材料を挟持して構成されることを特徴とする。The light control element according to claim 2 is characterized in that it is constructed by sandwiching the light control material according to claim 1 between a pair of substrates, at least one of which is transparent and has an electrode on the inner surface. .
【００１２】以下に本発明を詳細に説明する。本発明の
調光材料に含有される高分子は、前記一般式（Ｉ）で示
されるジアクリレート系化合物（以下「ジアクリレート
系化合物（Ｉ）」と称す。）及び前記一般式（ＩＩ）で
示されるモノアクリレート系化合物（以下「モノアクリ
レート系化合物（ＩＩ）」と称す。）から成る重合性組
成物を共重合させて得られるものである。The present invention will be explained in detail below. The polymer contained in the light control material of the present invention is a diacrylate compound represented by the general formula (I) (hereinafter referred to as "diacrylate compound (I)") and a diacrylate compound represented by the general formula (II). It is obtained by copolymerizing a polymerizable composition comprising the monoacrylate compound (hereinafter referred to as "monoacrylate compound (II)") shown below.
【００１３】前記一般式（Ｉ）において、Ｒは水素原子
又はメチル基を示し、ｎは１〜２５の整数、好ましくは
１０〜２５の整数である。また、前記一般式（ＩＩ）に
おいて、Ｒ１は水素原子又はメチル基を示し、Ｒ２はメ
チル基、エチル基、プロピル基、ブチル基、ペンチル基
、ヘキシル基、ヘプチル基、オクチル基、ノニル基、デ
シル基、ドデシル基、トリデシル基、ペンタデシル基、
ステアリル基等の炭素数１〜１８の直鎖状もしくは分岐
鎖状アルキル基；シクロヘキシル基；又はテトラヒドロ
フルフリル基を示す。In the general formula (I), R represents a hydrogen atom or a methyl group, and n is an integer of 1 to 25, preferably 10 to 25. Further, in the general formula (II), R1 represents a hydrogen atom or a methyl group, and R2 represents a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group. group, dodecyl group, tridecyl group, pentadecyl group,
It represents a linear or branched alkyl group having 1 to 18 carbon atoms such as a stearyl group; a cyclohexyl group; or a tetrahydrofurfuryl group.
【００１４】高分子の合成に用いるジアクリレート系化
合物（Ｉ）とモノアクリレート系化合物（ＩＩ）の使用
割合は、ジアクリレート系化合物（Ｉ）／モノアクリレ
ート系化合物（ＩＩ）＝１０／１〜１／１０（重量比）
の範囲が好ましく、特に１／１〜１０／１の範囲が好ま
しい。なお、ジアクリレート系化合物（Ｉ）及びモノア
クリレート系化合物（ＩＩ）は、各々、２種以上を混合
して用いても良い。The ratio of diacrylate compound (I) and monoacrylate compound (II) used in polymer synthesis is diacrylate compound (I)/monoacrylate compound (II) = 10/1 to 1. /10 (weight ratio)
The range is preferably 1/1 to 10/1, particularly preferably 1/1 to 10/1. Note that two or more of the diacrylate compounds (I) and monoacrylate compounds (II) may be used in combination.
【００１５】これらの重合性組成物は光又は熱により重
合させて、本発明に係る高分子を容易に合成することが
できる。これらの重合法のうち、光、特に紫外線による
重合が好ましく、この場合、光重合開始剤としては、２
，２−ジメトキシ−２−フェニルアセトフェノン、２−
ヒドロキシ−２−メチル−１−フェニルプロパン−１−
オン等、を用いることができる。[0015] These polymerizable compositions can be polymerized by light or heat to easily synthesize the polymer according to the present invention. Among these polymerization methods, polymerization using light, especially ultraviolet rays, is preferable, and in this case, as a photopolymerization initiator, 2
, 2-dimethoxy-2-phenylacetophenone, 2-
Hydroxy-2-methyl-1-phenylpropane-1-
On, etc. can be used.
【００１６】一方、液晶としては、ネマチック液晶、ス
メクチック液晶及びコレステリック液晶から成る群から
選ばれる１種又は２種以上の混合物が使用でき、上記高
分子の反応に対して不活性なものであれば特に制限され
ない。これらのうち、特にネマチック液晶がより好適に
使用される。On the other hand, as the liquid crystal, one type or a mixture of two or more types selected from the group consisting of nematic liquid crystal, smectic liquid crystal and cholesteric liquid crystal can be used, as long as it is inert to the reaction of the above-mentioned polymers. There are no particular restrictions. Among these, nematic liquid crystals are particularly preferably used.
【００１７】本発明で用いるネマチック液晶としては、
動作温度範囲でネマチック状態を示すものであれば、か
なり広い範囲で選択することができる。また、このよう
なネマチック液晶に後述の旋光性物質を加えることによ
り、コレステリック状態をとらせることができる。ネマ
チック液晶の例としては下記表１〜４に示される物質、
あるいはこれらの誘導体があげられる。The nematic liquid crystal used in the present invention is as follows:
As long as it exhibits a nematic state within the operating temperature range, it can be selected from a fairly wide range. Further, by adding an optically active substance to be described later to such a nematic liquid crystal, it can be made to take a cholesteric state. Examples of nematic liquid crystals include the substances shown in Tables 1 to 4 below,
Alternatively, these derivatives can be mentioned.
【００１８】[0018]
【表１】[Table 1]
【００１９】[0019]
【表２】[Table 2]
【００２０】[0020]
【表３】[Table 3]
【００２１】[0021]
【表４】[Table 4]
【００２２】上記表１〜４中、Ｒ３はアルキル基又はア
ルコキシ基を、Ｒ４はアルキル基を、Ｘはアルキル基、
アルコキシ基、ニトロ基、シアノ基、トリフルオロメチ
ル基、トリフルオロメトキシ基又はハロゲン原子を表わ
す。又、上記表１〜４中のベンゼン環は更にフッ素原子
で置換されても良い。In Tables 1 to 4 above, R3 is an alkyl group or an alkoxy group, R4 is an alkyl group, X is an alkyl group,
Represents an alkoxy group, nitro group, cyano group, trifluoromethyl group, trifluoromethoxy group or halogen atom. Moreover, the benzene rings in Tables 1 to 4 above may be further substituted with a fluorine atom.
【００２３】本発明で用いる液晶としては、表１〜４に
示した液晶又はそれらを含む混合物のいずれでも良いが
、例えば、メルク社からＺＬＩ−１１３２、ＺＬＩ−１
８４０或いはＺＬＩ−１５６５という商品名で販売され
ている液晶又はＢｒｉｔｉｓｈ Ｄｒｕｇ Ｈｏｕ
ｓｅ社からＥ−７，Ｅ−８，Ｅ−３７，Ｅ−４４，Ｅ−
４６或いはＢＬ００１〜ＢＬ０２０という商品名で販売
されている液晶等が使用される。The liquid crystal used in the present invention may be any of the liquid crystals shown in Tables 1 to 4 or mixtures containing them. For example, ZLI-1132 and ZLI-1 from Merck & Co.
LCD sold under the trade name 840 or ZLI-1565 or British Drug Hou
E-7, E-8, E-37, E-44, E- from SE company
Liquid crystals sold under the trade names 46 or BL001 to BL020 are used.
【００２４】また、このようなネマチック液晶に以下の
旋光性物質を加えることにより、コレステリック状態を
とらせることができる。Further, by adding the following optically active substance to such a nematic liquid crystal, it can be made to take a cholesteric state.
【００２５】この場合、旋光性物質としては、カイラル
ネマチック化合物、例えば、２−メチルブチル基、３−
メチルブトキシ基、３−メチルペンチル基、３−メチル
ペントキシ基、４−メチルヘキシル基、４−メチルヘキ
トキシ基などの光学活性基をネマチック液晶に導入した
化合物が挙げられる。また、特開昭５１−４５５４６号
に示すｌ−メントール、ｄ−ボルネオール等のアルコー
ル誘導体、ｄ−ショウノウ、３−メチルシクロヘキサン
等のケトン誘導体、ｄ−シトロネラ酸、ｌ−ショウノウ
酸等のカルボン酸誘導体、ｄ−シトロネラール等のアル
デヒド誘導体、ｄ−リノネン等のアルケン誘導体、その
他のアミン、アミド、ニトリル誘導体などの光学活性物
質を使用することができる。In this case, the optically active substance is a chiral nematic compound, such as a 2-methylbutyl group, a 3-
Examples include compounds in which optically active groups such as methylbutoxy, 3-methylpentyl, 3-methylpentoxy, 4-methylhexyl, and 4-methylhexyl groups are introduced into nematic liquid crystals. In addition, alcohol derivatives such as l-menthol and d-borneol, ketone derivatives such as d-camphor and 3-methylcyclohexane, and carboxylic acid derivatives such as d-citronellaic acid and l-camphoric acid as shown in JP-A-51-45546. , aldehyde derivatives such as d-citronellal, alkene derivatives such as d-linonene, and other optically active substances such as amine, amide, and nitrile derivatives can be used.
【００２６】更に、本発明で用いるスメクチック液晶と
しては、スメクチックＡ液晶、スメクチックカイラルＣ
液晶が挙げられる。Furthermore, as the smectic liquid crystal used in the present invention, smectic A liquid crystal, smectic chiral C
An example is liquid crystal.
【００２７】本発明において、調光材料中に占める前記
高分子の比率は６０〜１０重量％、特に３５〜１５重量
％とするのが好ましく、また、液晶の比率は４０〜９０
重量％、特に６５〜８５重量％とするのが好ましい。In the present invention, the proportion of the polymer in the light control material is preferably 60 to 10% by weight, particularly 35 to 15% by weight, and the proportion of liquid crystal is 40 to 90% by weight.
It is preferably 65 to 85% by weight.
【００２８】本発明の調光材料は、前記高分子及び液晶
の他、必要に応じて、界面活性剤、光安定化剤、色素、
連鎖移動剤、光増感剤、架橋剤等を含有していても良い
。In addition to the above-mentioned polymer and liquid crystal, the light control material of the present invention may optionally contain a surfactant, a light stabilizer, a pigment,
It may contain a chain transfer agent, a photosensitizer, a crosslinking agent, etc.
【００２９】このような調光材料は、例えば、ジアクリ
レート系化合物（Ｉ）、モノアクリレート系化合物（Ｉ
Ｉ）、必要に応じて重合開始剤、その他の添加剤、及び
液晶を混合し、含有されるジアクリレート系化合物（Ｉ
）及びモノアクリレート系化合物（ＩＩ）を共重合させ
て高分子を生成させることにより容易に調製することが
できる。Such light control materials include, for example, diacrylate compounds (I) and monoacrylate compounds (I).
I), if necessary, a polymerization initiator, other additives, and liquid crystal are mixed, and the diacrylate compound (I
) and monoacrylate compound (II) to form a polymer.
【００３０】例えば、液晶と重合性組成物を混合し、場
合により加熱して均一溶液とし、光重合開始剤及び他の
添加剤を添加した後、露光することにより重合性組成物
を共重合させる。その結果、液晶が共重合した高分子と
相分離し、本発明の調光材料を製造することができる。For example, the liquid crystal and the polymerizable composition are mixed, optionally heated to form a homogeneous solution, a photopolymerization initiator and other additives are added, and then the polymerizable composition is copolymerized by exposure to light. . As a result, the liquid crystal undergoes phase separation from the copolymerized polymer, and the light control material of the present invention can be manufactured.
【００３１】本発明の調光素子は、このような調光材料
を、少くとも一方が透明な、内面に電極を有する一対の
基板間に挟持して構成される。The light control element of the present invention is constructed by sandwiching such a light control material between a pair of substrates, at least one of which is transparent and has electrodes on its inner surface.
【００３２】本発明の調光素子の電極としてはＩＴＯ（
インジウム・スズ酸化物）等の透明電極が用いられ、ま
た、電極用基板としてはガラス又はポリエステル等のプ
ラスチック板のような透明基板が挙げられる。特に、一
対の透明な電極基板を使用する場合には、本発明の調光
素子を透過型調光素子として使用することができ、一方
が透明で他方が不透明な電極基板を使用する場合には、
不透明な電極基板の後に反射性層を置くことにより、本
発明の調光素子を反射型調光素子として使用することが
できる。As the electrode of the light control element of the present invention, ITO (
A transparent electrode such as indium tin oxide (indium tin oxide) is used, and the electrode substrate includes a transparent substrate such as a glass or a plastic plate such as polyester. In particular, when using a pair of transparent electrode substrates, the light control device of the present invention can be used as a transmission type light control device, and when using a pair of transparent electrode substrates and the other opaque, the light control device of the present invention can be used as a transmission type light control device. ,
By placing a reflective layer after the opaque electrode substrate, the light control device of the present invention can be used as a reflective light control device.
【００３３】[0033]
【作用】ジアクリレート系化合物（Ｉ）及びモノアクリ
レート系化合物（ＩＩ）を共重合して得られる高分子と
液晶を併用することにより、著しく優れた調光特性を有
する調光材料が得られる。[Operation] By using a liquid crystal together with a polymer obtained by copolymerizing diacrylate compound (I) and monoacrylate compound (II), a light control material having extremely excellent light control properties can be obtained.
【００３４】[0034]
【実施例】以下に実施例を挙げて本発明をより具体的に
説明するが、本発明はその要旨を超えない限り、以下の
実施例に限定されるものではない。[Examples] The present invention will be explained in more detail with reference to Examples below, but the present invention is not limited to the following Examples unless it exceeds the gist thereof.
【００３５】実施例１
モノアクリレート系化合物ＩＩａ（前記一般式（ＩＩ）
において、Ｒ１＝Ｒ２＝ＣＨ３）０．１ｇ、ジアクリレ
ート系化合物Ｉａ（前記一般式（Ｉ）において、Ｒ＝Ｃ
Ｈ３，ｎ＝１４）０．２ｇ、重合開始剤として２，２−
ジメトキシ−２−フェニルアセトフェノン０．００２ｇ
、及び、液晶としてＥ−８（ＢＤＨ社製）０．７ｇを混
合して、均一溶液を得、この溶液中に直径１４μｍのプ
ラスチック（ジビニルベンゼン共重合体）製スペーサー
０．０６ｇを入れた。この混合液を６×９ｃｍの大きさ
の２枚のＩＴＯ付プラスチック（ポリエチレンテレフタ
レート）基板のうちの１枚のＩＴＯ側に塗布した後、も
う１枚の基板のＩＴＯ側を重ね、紫外線照射装置により
露光することにより亀裂等のない均一な調光素子を得た
。なお、与えたエネルギーは８００ｍＪに相当する。Example 1 Monoacrylate compound IIa (formula (II) above)
, R1=R2=CH3) 0.1 g, diacrylate compound Ia (in the general formula (I), R=C
H3, n=14) 0.2 g, 2,2- as a polymerization initiator
Dimethoxy-2-phenylacetophenone 0.002g
, and 0.7 g of E-8 (manufactured by BDH) as a liquid crystal were mixed to obtain a homogeneous solution, and 0.06 g of a spacer made of plastic (divinylbenzene copolymer) having a diameter of 14 μm was placed in this solution. After applying this mixed solution to the ITO side of one of two ITO-coated plastic (polyethylene terephthalate) substrates with a size of 6 x 9 cm, the ITO side of the other substrate was placed on top of the other substrate, and the substrate was exposed to ultraviolet irradiation equipment. By exposing to light, a uniform light control element without cracks etc. was obtained. Note that the applied energy corresponds to 800 mJ.
【００３６】得られた調光素子に電界を印加しない場合
（ｂ）、及び、１００Ｖの交流（５００Ｈｚ、正弦波）
を印加した場合（ａ）の透過率スペクトルを第１図に示
す。なお、電界を印加したものから、電界を外すと元の
電界を印加しないスペクトルに戻ることが確認された。
第１図に示す如く、得られた素子は広い波長領域にわた
って良好な透過率差を示した。特に、７５０ｎｍの波長
で見ると、５９％の透過率差を示した。[0036] When no electric field is applied to the obtained dimming device (b), and when 100V AC (500Hz, sine wave)
FIG. 1 shows the transmittance spectrum of (a) when . It was confirmed that when an electric field was applied, when the electric field was removed, the spectrum returned to the original without applying an electric field. As shown in FIG. 1, the obtained device showed a good transmittance difference over a wide wavelength range. In particular, when viewed at a wavelength of 750 nm, a transmittance difference of 59% was observed.
【００３７】実施例２
実施例１で用いたモノアクリレート系化合物ＩＩａ０．
０５ｇ、ジアクリレート系化合物Ｉａ０．２５ｇ、重合
開始剤として２，２−ジメトキシ−２−フェニルアセト
フェノン０．００２ｇ、及び、液晶としてＥ−８（ＢＤ
Ｈ社製）０．７ｇを使用し、他は実施例１と同様に処理
して、亀裂等のない均一な調光素子を作成した。Example 2 Monoacrylate compound IIa0.0 used in Example 1.
05g, diacrylate compound Ia 0.25g, 2,2-dimethoxy-2-phenylacetophenone 0.002g as a polymerization initiator, and E-8 (BD
(manufactured by Company H) was used, and the other processes were carried out in the same manner as in Example 1 to produce a uniform light control element with no cracks or the like.
【００３８】得られた調光素子に電界を印加しない場合
（ｂ）、及び、１００Ｖの交流（５００Ｈｚ、正弦波）
を印加した場合（ａ）の透過率スペクトルを第２図に示
す。なお、電界を印加したものから、電界を外すと元の
電界を印加しないスペクトルに戻ることが確認された。
第２図に示す如く、得られた素子は広い波長領域にわた
って良好な透過率差を示した。特に、８００ｎｍの波長
で見ると、６０％の透過率差を示した。[0038] When no electric field is applied to the obtained dimming device (b), and when 100V AC (500Hz, sine wave)
FIG. 2 shows the transmittance spectrum of (a) when . It was confirmed that when an electric field was applied, when the electric field was removed, the spectrum returned to the original without applying an electric field. As shown in FIG. 2, the obtained device showed a good transmittance difference over a wide wavelength range. In particular, when viewed at a wavelength of 800 nm, a transmittance difference of 60% was observed.
【００３９】実施例３
モノアクリレート系化合物ＩＩｂ（前記一般式（ＩＩ）
において、Ｒ１＝Ｈ，Ｒ２＝Ｃ４Ｈ９（ｎ））０．１ｇ
、実施例１で用いたジアクリレート系化合物Ｉａ０．２
ｇ、重合開始剤として２，２−ジメトキシ−２−フェニ
ルアセトフェノン０．００２ｇ、及び、液晶としてＥ−
８（ＢＤＨ社製）０．７ｇを使用し、他は実施例１と同
様に処理して、亀裂等のない均一な調光素子を作成した
。Example 3 Monoacrylate compound IIb (formula (II) above)
, R1=H, R2=C4H9(n)) 0.1g
, diacrylate compound Ia0.2 used in Example 1
g, 0.002 g of 2,2-dimethoxy-2-phenylacetophenone as a polymerization initiator, and E- as a liquid crystal.
8 (manufactured by BDH Co., Ltd.) was used, and the other processes were carried out in the same manner as in Example 1 to produce a uniform light control element with no cracks or the like.
【００４０】得られた調光素子に電界を印加しない場合
（ｂ）、及び、１００Ｖの交流（５００Ｈｚ、正弦波）
を印加した場合（ａ）の透過率スペクトルを第３図に示
す。なお、電界を印加したものから、電界を外すと元の
電界を印加しないスペクトルに戻ることが確認された。
第３図に示す如く、得られた素子は広い波長領域にわた
って良好な透過率差を示した。特に、６８０ｎｍの波長
で見ると、７０％の透過率差を示した。[0040] When no electric field is applied to the obtained dimming device (b), and when 100V AC (500Hz, sine wave)
FIG. 3 shows the transmittance spectrum of (a) when . It was confirmed that when an electric field was applied, when the electric field was removed, the spectrum returned to the original without applying an electric field. As shown in FIG. 3, the obtained device showed a good transmittance difference over a wide wavelength range. In particular, when viewed at a wavelength of 680 nm, a transmittance difference of 70% was observed.
【００４１】実施例４〜１０
下記表５に示すジアクリレート系化合物（Ｉ）、モノア
クリレート系化合物（ＩＩ）及び液晶を表５に示す割合
で混合使用し、他は、実施例１と同様に処理して、亀裂
等のない均一な調光素子を作成した。得られた素子につ
いて、１００Ｖの交流（５００Ｈｚ、正弦波）印加時と
無印加時の、波長６００ｎｍにおける透過率差を測定し
、結果を表５に示した。Examples 4 to 10 The diacrylate compound (I), monoacrylate compound (II), and liquid crystal shown in Table 5 below were mixed and used in the proportions shown in Table 5, and the other conditions were the same as in Example 1. After processing, a uniform light control element with no cracks or the like was created. Regarding the obtained element, the transmittance difference at a wavelength of 600 nm was measured when 100 V alternating current (500 Hz, sine wave) was applied and when no voltage was applied, and the results are shown in Table 5.
【００４２】[0042]
【表５】[Table 5]
【００４３】[0043]
【発明の効果】以上詳述した通り、本発明の調光材料は
、任意の透過率、繰り返し応答性、電圧感受性、応答速
度、膜の均一性、耐光性、耐熱性、耐水性等の耐久性等
の調光素子に要求される特性を十分に満足し、特に、膜
の均一性が良好であり、該調光材料を使用した調光素子
は電界印加時と無印加時の透過率差、繰り返し応答性等
に著しく優れる。従って、本発明の調光素子は、表示装
置、調光窓等に極めて有用である。Effects of the Invention As detailed above, the light control material of the present invention has excellent durability such as arbitrary transmittance, repeated response, voltage sensitivity, response speed, film uniformity, light resistance, heat resistance, water resistance, etc. It fully satisfies the properties required for light control elements such as properties, and in particular, the uniformity of the film is good, and light control elements using this light control material have a small transmittance difference between when an electric field is applied and when no electric field is applied. , excellent repeatability, etc. Therefore, the light control element of the present invention is extremely useful for display devices, light control windows, etc.
【図１】第１図は実施例１で得られた調光素子の透過率
スペクトルを示すグラフである。FIG. 1 is a graph showing the transmittance spectrum of the light control element obtained in Example 1.
【図２】第２図は実施例２で得られた調光素子の透過率
スペクトルを示すグラフである。FIG. 2 is a graph showing the transmittance spectrum of the light control element obtained in Example 2.
【図３】第３図は実施例３で得られた調光素子の透過率
スペクトルを示すグラフである。FIG. 3 is a graph showing the transmittance spectrum of the light control element obtained in Example 3.
Claims (2)
印加の有無により、光の透過散乱を制御する調光材料に
おいて、前記高分子が、一般式（Ｉ） 【化１】 （式中、Ｒは水素原子又はメチル基を示し、ｎは１〜２
５の整数を示す。）で示されるジアクリレート系化合物
及び一般式（ＩＩ） 【化２】 （式中、Ｒ１は水素原子又はメチル基を示し、Ｒ２は炭
素数１〜１８のアルキル基、シクロヘキシル基又はテト
ラヒドロフルフリル基を示す。）で示されるモノアクリ
レート系化合物から成る重合性組成物を共重合させて得
られる高分子であることを特徴とする調光材料。Claim 1. A light control material comprising a liquid crystal and a polymer and controlling the transmission and scattering of light depending on the presence or absence of an electric field, wherein the polymer has the general formula (I) , R represents a hydrogen atom or a methyl group, and n is 1-2
Indicates an integer of 5. ) and general formula (II) [Formula 2] (wherein, R1 represents a hydrogen atom or a methyl group, and R2 represents an alkyl group having 1 to 18 carbon atoms, a cyclohexyl group, or a tetrahydrofurfuryl group) A light control material characterized in that it is a polymer obtained by copolymerizing a polymerizable composition comprising a monoacrylate compound represented by:
有する一対の基板間に請求項１に記載の調光材料を挟持
して構成されることを特徴とする調光素子。2. A light control element comprising a light control material according to claim 1 sandwiched between a pair of substrates, at least one of which is transparent and having electrodes on the inner surface.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8516991A JPH04317025A (en) | 1991-04-17 | 1991-04-17 | Light control material and light control element containing this material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8516991A JPH04317025A (en) | 1991-04-17 | 1991-04-17 | Light control material and light control element containing this material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04317025A true JPH04317025A (en) | 1992-11-09 |
Family
ID=13851162
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8516991A Pending JPH04317025A (en) | 1991-04-17 | 1991-04-17 | Light control material and light control element containing this material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04317025A (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001270848A (en) * | 2000-01-19 | 2001-10-02 | Asahi Glass Co Ltd | Acrylic acid derivative compound, polymeric liquid crystal prepared by polymerizing the same and use thereof |
| JP2004125868A (en) * | 2002-09-30 | 2004-04-22 | Hitachi Chem Co Ltd | Sheet for liquid crystal display device, and method for manufacturing liquid crystal display device using the same |
| US7176261B2 (en) * | 2004-10-21 | 2007-02-13 | Medtronic, Inc. | Angiotensin-(1-7) eluting polymer-coated medical device to reduce restenosis and improve endothelial cell function |
| WO2008096509A1 (en) | 2007-02-06 | 2008-08-14 | Adeka Corporation | Polymerizable optically-active compound, and polymerizable composition comprising the polymerizable optically-active compound |
| WO2010032591A1 (en) | 2008-09-18 | 2010-03-25 | 株式会社Adeka | Polymerizable optically active imide compound and polymerizable composition containing the compound |
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-
1991
- 1991-04-17 JP JP8516991A patent/JPH04317025A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001270848A (en) * | 2000-01-19 | 2001-10-02 | Asahi Glass Co Ltd | Acrylic acid derivative compound, polymeric liquid crystal prepared by polymerizing the same and use thereof |
| JP2004125868A (en) * | 2002-09-30 | 2004-04-22 | Hitachi Chem Co Ltd | Sheet for liquid crystal display device, and method for manufacturing liquid crystal display device using the same |
| JP4599792B2 (en) * | 2002-09-30 | 2010-12-15 | 日立化成工業株式会社 | Sheet for liquid crystal display device and method for manufacturing liquid crystal display device using the same |
| US7176261B2 (en) * | 2004-10-21 | 2007-02-13 | Medtronic, Inc. | Angiotensin-(1-7) eluting polymer-coated medical device to reduce restenosis and improve endothelial cell function |
| WO2008096509A1 (en) | 2007-02-06 | 2008-08-14 | Adeka Corporation | Polymerizable optically-active compound, and polymerizable composition comprising the polymerizable optically-active compound |
| US7910021B2 (en) | 2007-02-06 | 2011-03-22 | Adeka Corporation | Polymerizable optical active compound and polymerizable composition containing the same |
| WO2010032591A1 (en) | 2008-09-18 | 2010-03-25 | 株式会社Adeka | Polymerizable optically active imide compound and polymerizable composition containing the compound |
| KR20110056475A (en) | 2008-09-18 | 2011-05-30 | 가부시키가이샤 아데카 | Polymerizable optically active imide compound and polymerizable composition containing the compound |
| US8512597B2 (en) | 2008-09-18 | 2013-08-20 | Adeka Corporation | Polymerizable optically active imide compound and polymerizable composition containing the compound |
| JP5875028B2 (en) * | 2013-08-13 | 2016-03-02 | Dic株式会社 | Composite liquid crystal composition, display element and electric field detector |
| CN105492578A (en) * | 2013-08-13 | 2016-04-13 | Dic株式会社 | Composite liquid crystal composition, display element and electric field detector |
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