JPH02208306A - Production of new photoreactive thin-film polymer - Google Patents
Production of new photoreactive thin-film polymerInfo
- Publication number
- JPH02208306A JPH02208306A JP2841889A JP2841889A JPH02208306A JP H02208306 A JPH02208306 A JP H02208306A JP 2841889 A JP2841889 A JP 2841889A JP 2841889 A JP2841889 A JP 2841889A JP H02208306 A JPH02208306 A JP H02208306A
- Authority
- JP
- Japan
- Prior art keywords
- polymer
- film
- thin film
- light
- monomolecular film
- 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.)
- Granted
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 34
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000010409 thin film Substances 0.000 title abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 150000002148 esters Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229920001651 Cyanoacrylate Polymers 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000010408 film Substances 0.000 abstract description 22
- 239000000463 material Substances 0.000 abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 8
- 238000000034 method Methods 0.000 abstract description 7
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract description 5
- 239000007788 liquid Substances 0.000 abstract description 4
- 238000010894 electron beam technology Methods 0.000 abstract description 3
- 239000000758 substrate Substances 0.000 abstract description 3
- 238000001393 microlithography Methods 0.000 abstract description 2
- 230000003287 optical effect Effects 0.000 abstract description 2
- 238000007654 immersion Methods 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 11
- 238000010521 absorption reaction Methods 0.000 description 9
- 239000010453 quartz Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 238000000862 absorption spectrum Methods 0.000 description 7
- 239000013078 crystal Substances 0.000 description 5
- 238000007598 dipping method Methods 0.000 description 5
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 229910052724 xenon Inorganic materials 0.000 description 3
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- -1 olefin compound Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- OCOCSIDEWXUOQN-UHFFFAOYSA-N 2-cyanopenta-2,4-dienoic acid Chemical compound OC(=O)C(C#N)=CC=C OCOCSIDEWXUOQN-UHFFFAOYSA-N 0.000 description 1
- ZZAGLMPBQOKGGT-UHFFFAOYSA-N [4-[4-(4-prop-2-enoyloxybutoxy)benzoyl]oxyphenyl] 4-(4-prop-2-enoyloxybutoxy)benzoate Chemical compound C1=CC(OCCCCOC(=O)C=C)=CC=C1C(=O)OC(C=C1)=CC=C1OC(=O)C1=CC=C(OCCCCOC(=O)C=C)C=C1 ZZAGLMPBQOKGGT-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- NFURDKBDRIUBCV-UHFFFAOYSA-N dodecyl 3-[4-(3-dodecoxy-3-oxoprop-1-enyl)phenyl]prop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C=CC1=CC=C(C=CC(=O)OCCCCCCCCCCCC)C=C1 NFURDKBDRIUBCV-UHFFFAOYSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は新規な光反応性薄膜状重合体の製造方法に関す
るものである。さらに詳しくいえば、本発明は各種の電
子デバイス作製用や、ミクロリングラフイーにおける電
子線レジスト材料などとして利用可能な、シクロブタン
環を有する重合体を薄膜状に製造する方法に関するもの
である。本発明において、薄膜を作製するのに用いられ
る重合体は構造式（Ｉ）で示され、棒状で剛直なある種
のオレフィン化合物の結晶に光照射することにより得ら
れる。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing a novel photoreactive thin film polymer. More specifically, the present invention relates to a method for producing a thin film of a polymer having a cyclobutane ring, which can be used for producing various electronic devices and as an electron beam resist material in microphosphorography. In the present invention, the polymer used to prepare the thin film is represented by the structural formula (I), and is obtained by irradiating a rod-shaped and rigid crystal of a certain type of olefin compound with light.
（式中のＲは水素またはシアノ残基Ｒ″は炭素数６〜２
２の飽和アルキル基を有するエステル残基または炭素数
６〜２２の飽和アルキル基を有するシアノアクリル酸エ
ステル残基、ｎは２〜２００の整数である。〉
この重合体は化学的、物理的特性から感光性材料、電子
デバイス材料として期待されているが、結晶性が非常に
高く、有機溶媒に溶解しにくいため粉明の目的は、感光
性材料などとして有用で、また各種電子デバイス作製用
や、ミクロリソグラフィーにおける電子線レジスト材料
などとして利用可能な、主鎖にシクロブタン環を有する
新規な薄膜状重合体を提供することにある。(R in the formula is hydrogen or cyano residue R″ has 6 to 2 carbon atoms.
an ester residue having 2 saturated alkyl groups or a cyanoacrylate ester residue having a saturated alkyl group having 6 to 22 carbon atoms; n is an integer of 2 to 200; 〉 This polymer is expected to be used as a photosensitive material and electronic device material due to its chemical and physical properties, but it is highly crystalline and difficult to dissolve in organic solvents, so the purpose of powdering is to use it as a photosensitive material, etc. It is an object of the present invention to provide a novel thin film polymer having a cyclobutane ring in its main chain, which is useful as a material for producing various electronic devices and as an electron beam resist material in microlithography.
ところで一定の分子配列を有し、オングストロームのオ
ーダーで一定の厚さを持つ薄膜の調整方法としては、ラ
ングミュアブロジェット法が知られている。この方法を
用いて薄膜を調整するには、分子内に親水性部分と長鎖
アルキル基などの疎水性部分を有することが必要とされ
ている。上記重合体の骨格構造はその条件を満たしてい
ないが本発明者は鋭意研究を重ねた結果、上記重合体に
おいてエステル残基中に疎水性部分として長鎖アルキル
基を有する重合体は、適当な両親媒性化合物、例えばア
ラキン酸、ステアリルアルコールなどと混合することに
より、水面上あるいは塩化カドミウム水溶液などの液面
上に安定な混合単分子膜を形成することを見い出した。By the way, the Langmuir-Blodgett method is known as a method for preparing a thin film having a constant molecular arrangement and a constant thickness on the order of angstroms. In order to prepare a thin film using this method, it is necessary to have a hydrophilic portion and a hydrophobic portion such as a long-chain alkyl group in the molecule. Although the skeleton structure of the above polymer does not satisfy this condition, the present inventor has conducted extensive research and found that the above polymer has a long chain alkyl group as a hydrophobic moiety in the ester residue. We have discovered that by mixing with amphiphilic compounds such as arachidic acid and stearyl alcohol, a stable mixed monomolecular film can be formed on the surface of water or a liquid such as an aqueous cadmium chloride solution.
このような単分子膜の形成は、表面圧−占有面積曲線に
おいて、固体凝縮相の存在が確認されたことから明らか
である。The formation of such a monomolecular film is evident from the confirmation of the presence of a solid condensed phase in the surface pressure-occupied area curve.
このような状態の単分子膜は垂直浸せき法により、適当
な基板に移しとることができる。すなわち、本発明は一
般式（Ｉ）で表わされる重合体と両親媒性化合物を適当
なモル比で混合し混合単分子膜を形成させ、それを垂直
浸せき法により基板に移しとることにより分子のオーダ
ーて膜厚の調整可能な薄膜状重合体を作製する方法を提
供する。A monomolecular film in such a state can be transferred to a suitable substrate by a vertical dipping method. That is, in the present invention, the polymer represented by the general formula (I) and the amphiphilic compound are mixed in an appropriate molar ratio to form a mixed monomolecular film, and the resulting monolayer is transferred to a substrate by a vertical dipping method, thereby forming molecules. Provided is a method for producing a thin film polymer whose film thickness can be adjusted to order.
次に、該薄膜の好適な調整方法の１例について説明する
と、まず長鎖アルキル基を有する重合体、例えば、ポＩ
Ｊ （ｐ−フェニレンジアクリル酸ジドデシルエステ
ル）とアラキン酸などのような両親媒性化合物とをモル
比１：５ないし１：４の割合で、クロロホルムなどの有
機溶媒に溶解した後、この溶液を蒸留水あるいは塩化カ
ドミウム水溶液などの液面上に徐々に滴下後、圧縮し、
該液面上は累積する回数により調整できる。このように
して作製された薄膜は無色透明であり感光性である。Next, one example of a suitable method for preparing the thin film will be explained. First, polymers having long chain alkyl groups, such as poly
J (p-phenylene diacrylic acid didodecyl ester) and an amphiphilic compound such as arachidic acid are dissolved in an organic solvent such as chloroform at a molar ratio of 1:5 to 1:4, and then this solution is dissolved. is gradually dropped onto the surface of a liquid such as distilled water or cadmium chloride solution, and then compressed.
The liquid level can be adjusted by the cumulative number of times. The thin film thus produced is colorless, transparent, and photosensitive.
例えば、ポリ （ｐ−７エニレンジアクリル酸ジドデシ
ルエステル）の薄膜にシクロブタン環を開裂させると考
えられている波長の光（２２４ｎｍ） を照射すると
２９０ｎｍ付近の吸光度が照射時間の経過と共に増加し
てくる。この照射した薄膜の分子量をゲルパーミェーシ
ョンクロマトグラフィーにより測定した結果、３〜４量
体に相当するオリゴマーであることがわかり、このこと
は主鎖中のシクロブタン環が光照射により開裂し、解重
合が起っ゛たことを示している。このオリゴマーの薄膜
に極大吸収２９Ｏｎｍ付近の光を照射すると吸収極大は
徐々に減少、消失し重合体の吸収スペクトルとなる。こ
のことは、再照射によりオリゴマーから重合体への変化
が起った事を示しており、この過程は繰り返すことが可
能である。すなわち、本発明の製造方法による薄膜状重
合体は光照射により可逆解重合性を有するものであるこ
とを示す。この光可逆解重合性は用いた重合体が粉抹状
の場合は観察されず、本製造方法により作製された薄膜
状重合体にのみ起る特異的なもので、この特性を活かし
て、これらは光記録材料、各種デバイス作製用などとし
て利用可能である。For example, when a thin film of poly(p-7 enylene diacrylic acid didodecyl ester) is irradiated with light at a wavelength (224 nm) that is thought to cleave the cyclobutane ring, the absorbance around 290 nm increases with the passage of irradiation time. come. As a result of measuring the molecular weight of this irradiated thin film by gel permeation chromatography, it was found that it is an oligomer corresponding to a trimer or tetramer, which means that the cyclobutane ring in the main chain is cleaved by light irradiation. This indicates that depolymerization has occurred. When this oligomer thin film is irradiated with light having a maximum absorption of around 29 Onm, the absorption maximum gradually decreases and disappears, resulting in an absorption spectrum of a polymer. This indicates that a change from oligomer to polymer occurred upon re-irradiation, and this process can be repeated. That is, it is shown that the thin film polymer produced by the production method of the present invention has reversible depolymerizability upon irradiation with light. This photoreversible depolymerizability is not observed when the polymer used is in the form of powder, and is unique to the thin film polymer produced by this production method. It can be used as an optical recording material and for manufacturing various devices.
実施例
次に実施例により本発明をさらに詳細に説明するが、本
発明はこれらの例によってなんら限定されるものではな
い。EXAMPLES Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples in any way.
実施例１
エタノールから数回再結晶することにより精製したｐ−
フェニレンジアクリル酸ジドデシルエステル（ｌｏｏｍ
ｇ＞の結晶を水中で攪拌、分散させ５００Ｗキセノンラ
ンプで１時間照射すると定量的に高分子量重合体が得ら
れる。この重合体のクロロホルム溶液（Ｉ Ｘｌ０−’
Ｍ）とアラキン酸のクロロホルム溶液（１−プ）１０−
’ Ｍ ）をモル比１：５の割合で体の吸収スペクトル
となり、再び重合体となった。Example 1 p- purified by several recrystallizations from ethanol
Phenylene diacrylic acid didodecyl ester (LOOM
A high molecular weight polymer can be quantitatively obtained by stirring and dispersing the crystals of g> in water and irradiating the crystals with a 500W xenon lamp for 1 hour. A chloroform solution of this polymer (I
M) and chloroform solution of arachidic acid (1-p) 10-
'M) at a molar ratio of 1:5, resulting in the absorption spectrum of a polymer, and it became a polymer again.
徐々に滴下して展開後、圧縮し単分子を形成させた。表
面圧−占有面積曲線から２０ ３０ｄｙｎ／ｃｍで固体
凝縮相の存在が確認されたので、表面圧を２０ｈｙｎ／
ｃｍに設定して、単分子膜を形成させた。この単分子膜
を垂直浸せき法により、石英板に移しとった。この時、
石英板の下降、上昇時共に単分子膜が石英板に移行し、
この操作をくり返すことにより、単分子膜が石英板に累
積される。このようにして２０層累積した薄膜は無色透
明であり、２６０ｎｍ以上の領域に吸収はない。この薄
膜に単色光照射装置を用いて２２４ｎｍの光を６０秒照
射すると薄膜の吸収スペクトルは２９０ｎｍに吸収極大
を有する吸収スペクトルとなった。この時の薄膜をテト
ラビトロフランに溶解して、ゲルパーミェーションクロ
マトグラフィーにより、その分子量を測定すると３〜４
量体であり重合体はオリゴマーへ解重合したことがわか
った。この薄膜に再び２９０実施例２
アセトンから再結晶をして精製した５、５″（１，４−
フェニレン）−ビス（２−シアノ−２゜４−ペンクジエ
ノインク酸）ジドデシルエステル（１００ｍｇ）の結晶
を水中で攪拌、分散させ５００Ｗキセノンランプで３０
分間光照射すると定量的に重合体が得られる。この重合
体のクロロホルム溶液（Ｉ Ｘ １０−３Ｍ＞とアラキ
ン酸のクロロホルム溶液（Ｉ Ｘ １０−３Ｍ）をモル
比１：４の割合で混合した溶液を蒸留水の液面上の展開
後、圧縮し単分子膜を形成させた。表面圧−占有面積曲
線から２０３０ｄｙｎ／ｃｍで固体凝縮相の存在が確認
さたので、表面圧を２５ｄＶｎ／ｃｍに設定して、単分
子膜を形成させた。この単分子膜を垂直浸せき法により
、ガラス板に移しとった。この時、石英板の下降、上昇
時共に単分子膜はガラス板に移行し、この操作をくり返
す、ことにより２０層の累積膜を作製した。こｎｍの光
を照射すると吸収極大は徐々に減少し重合あられれる。After being gradually dropped and expanded, it was compressed to form a single molecule. The presence of a solid condensed phase was confirmed from the surface pressure-occupied area curve at 20 to 30 dyn/cm, so the surface pressure was changed to 20 hyn/cm.
cm to form a monolayer. This monomolecular film was transferred to a quartz plate by a vertical dipping method. At this time,
When the quartz plate descends and rises, the monomolecular film transfers to the quartz plate,
By repeating this operation, a monomolecular film is accumulated on the quartz plate. The thin film obtained by accumulating 20 layers in this manner is colorless and transparent, and has no absorption in the region of 260 nm or more. When this thin film was irradiated with 224 nm light for 60 seconds using a monochromatic light irradiation device, the absorption spectrum of the thin film became an absorption spectrum having an absorption maximum at 290 nm. The thin film at this time was dissolved in tetravitrofuran and its molecular weight was measured by gel permeation chromatography.
It was found that the polymer was depolymerized into an oligomer. This thin film was again coated with 290 Example 2 5,5'' (1,4-
Crystals of (phenylene)-bis(2-cyano-2°4-pencdienoincic acid) didodecyl ester (100 mg) were stirred and dispersed in water, and the mixture was heated with a 500 W xenon lamp for 30 min.
When irradiated with light for a minute, the polymer can be obtained quantitatively. A solution prepared by mixing a chloroform solution of this polymer (I x 10-3M) and a chloroform solution of arachidic acid (I x 10-3M) at a molar ratio of 1:4 was spread on the surface of distilled water, and then compressed. Since the presence of a solid condensed phase was confirmed from the surface pressure-occupied area curve at 2030 dVn/cm, a monomolecular film was formed by setting the surface pressure to 25 dVn/cm. This monomolecular film was transferred to a glass plate by the vertical dipping method.At this time, the monomolecular film was transferred to the glass plate both when the quartz plate was lowered and raised, and this operation was repeated, resulting in an accumulation of 20 layers. A film was prepared. When irradiated with light of this nm, the absorption maximum gradually decreases and polymerization occurs.
この状態における薄膜の分子量をゲルパーミェーション
クロマトグラフィーで調べると２〜３量体のオリゴマー
であることがわかった。When the molecular weight of the thin film in this state was examined by gel permeation chromatography, it was found that it was a dimer to trimer oligomer.
この薄膜に３６０ｎｍの光を照射すると吸収極大は徐々
に減少し、重合体と同じ吸収スペクトルとなり、再び重
合したことがわかった。この過程は数回繰り返すことが
可能であった。When this thin film was irradiated with 360 nm light, the absorption maximum gradually decreased and the absorption spectrum became the same as that of the polymer, indicating that it had been polymerized again. This process could be repeated several times.
実施例３
アセトンから再結晶して精製した５、５”−（１４−フ
ェニレン）−ビス（２−シアノ−２，４ペンタジエノイ
ンク酸）ジドデシルエステル（１００ｍｇ）の結晶を水
中で攪拌、分散させ５００Ｗキセノンランプを光源とし
フィルター（コーニングＮ０１３７２）を用いて４３０
ｎｍ以上の光を６０分照射すると定量的に分子量２．０
００から３．０００の黄色の低重合体が得られる。この
低重合体のクロロホルム溶液（ＩＸＩＯ−３Ｍ）とアラ
キン酸のクロロホルム溶液（ＩＸＩＯ−’１ｖｌ）をモ
ル比１；５の割合で混合した溶液を蒸留水の液面上に徐
々に滴下して展開後圧綿し単分子膜を形成させた。表面
圧−占有面積曲線から２０〜３０ｄｙｎ／印で固体凝縮
相の存在が確認されたので、表面圧を２０ｄｙｎ／ｃｍ
に設定して、単分子膜を形成させた。この単分子膜を垂
直浸せき法により、石英板に移しとった。この時、石英
板の下降、上昇時共に単分子膜が石英板に移行し、この
操作をくり返すことにより、３０層の累積膜を作製した
。このようにして作製された薄膜は黄色透明であり、３
６０ｎ＋ｎに吸収極大を持つ。この薄膜に３６０ｎｍの
光を３分間照射すると３６０ｎｍの吸収極大は消失し分
子量の高い重合体となった。この薄膜状重合体に２８９
ｎｍの光を照射すると、薄膜の吸収スペクトルは再び３
６０ｎｍに吸収極大を有するオリゴマーの吸収スペクト
ルとなる。この低重合体から高重合体またこの逆の変化
は光照射により可逆的に起ることがわかった。Example 3 Crystals of 5,5''-(14-phenylene)-bis(2-cyano-2,4pentadienoic acid) didodecyl ester (100 mg) purified by recrystallization from acetone were stirred in water, Using a dispersed 500W xenon lamp as a light source and a filter (Corning N01372),
When irradiated with light of nm or more for 60 minutes, the molecular weight quantitatively becomes 2.0.
00 to 3.000 is obtained. A solution of a chloroform solution of this low polymer (IXIO-3M) and a chloroform solution of arachidic acid (IXIO-'1vl) mixed at a molar ratio of 1:5 was gradually dropped onto the surface of distilled water to develop it. A monomolecular film was formed by post-pressing. The presence of a solid condensed phase was confirmed from the surface pressure-occupied area curve at 20 to 30 dyn/cm, so the surface pressure was set to 20 dyn/cm.
was set to form a monomolecular film. This monomolecular film was transferred to a quartz plate by a vertical dipping method. At this time, the monomolecular film was transferred to the quartz plate both when the quartz plate was lowered and raised, and by repeating this operation, a cumulative film of 30 layers was produced. The thin film produced in this way is yellow transparent and 3
It has an absorption maximum at 60n+n. When this thin film was irradiated with 360 nm light for 3 minutes, the absorption maximum at 360 nm disappeared and a polymer with a high molecular weight was formed. This thin film polymer has 289
When irradiated with light of 3 nm, the absorption spectrum of the thin film changes again to 3 nm.
This is an absorption spectrum of an oligomer having an absorption maximum at 60 nm. It was found that this change from low polymer to high polymer and vice versa occurs reversibly by light irradiation.
Claims (1)
２の飽和アルキル基を有するエステル残基または炭素数
６〜２２の飽和アルキル基を有するシアノアクリル酸エ
ステル残基、ｎは２〜２００の整数である。） で表わされる重合体と両親媒性化合物との混合物からな
る混合単分子膜を形成し、累積することにより、光反応
性膜とすることを特徴とする薄膜状重合体の製造方法。(1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (R in the formula is hydrogen or cyano residue R' has 6 to 2 carbon atoms.
an ester residue having 2 saturated alkyl groups or a cyanoacrylate ester residue having a saturated alkyl group having 6 to 22 carbon atoms; n is an integer of 2 to 200; ) A method for producing a thin film-like polymer, which comprises forming a mixed monomolecular film consisting of a mixture of a polymer represented by the above formula and an amphipathic compound and accumulating the mixture to form a photoreactive film.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2841889A JPH02208306A (en) | 1989-02-07 | 1989-02-07 | Production of new photoreactive thin-film polymer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2841889A JPH02208306A (en) | 1989-02-07 | 1989-02-07 | Production of new photoreactive thin-film polymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02208306A true JPH02208306A (en) | 1990-08-17 |
| JPH0368044B2 JPH0368044B2 (en) | 1991-10-25 |
Family
ID=12248107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2841889A Granted JPH02208306A (en) | 1989-02-07 | 1989-02-07 | Production of new photoreactive thin-film polymer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02208306A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007270146A (en) * | 2006-03-10 | 2007-10-18 | Nagoya Institute Of Technology | Electroconductive polymer thin film for display element, method for producing the same and electrochromic display element using the same |
-
1989
- 1989-02-07 JP JP2841889A patent/JPH02208306A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007270146A (en) * | 2006-03-10 | 2007-10-18 | Nagoya Institute Of Technology | Electroconductive polymer thin film for display element, method for producing the same and electrochromic display element using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0368044B2 (en) | 1991-10-25 |
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