JP4756501B2 - Method for producing photodegradable polymer compound - Google Patents
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Description
本発明は、光照射することにより分解する光分解性高分子化合物の製造方法に関し、更に詳細には、紫外光、可視光などの光を照射することにより、光分解性部位が開裂し、分解する光分解性高分子化合物の製造方法に関する。 The present invention relates to a method for producing a photodegradable polymer compound that is decomposed by light irradiation. More specifically, the photodegradable site is cleaved and decomposed by irradiation with light such as ultraviolet light and visible light. The present invention relates to a method for producing a photodegradable polymer compound.
近年、環境汚染が叫ばれる中、再利用の出来る高分子化合物や、環境中で簡単に分解のできる高分子化合物の研究が種々なされおり、例えば、生分解性高分子化合物や光分解性高分子化合物等についての種々の研究がなされている。 In recent years, various researches have been conducted on polymer compounds that can be reused and polymer compounds that can be easily decomposed in the environment while environmental pollution is screamed. For example, biodegradable polymer compounds and photodegradable polymers Various studies have been conducted on compounds and the like.
このうち、光分解性高分子化合物を利用したものとしては、例えば、フェニルイソプロペニルケトンを共重合した電子写真用トナーが提案されている（特許文献１）。しかし、この公報に記載されているものは、合成方法が煩雑であること、フェニルイソプロペニルケトンが重合性単量体としての安定性に劣ること、重合後の高分子化合物が光分解の感度に劣る等の欠点があった。 Among these, for example, an electrophotographic toner obtained by copolymerizing phenyl isopropenyl ketone has been proposed as one using a photodegradable polymer compound (Patent Document 1). However, what is described in this publication is that the synthesis method is complicated, that phenyl isopropenyl ketone is inferior in stability as a polymerizable monomer, and that the polymer compound after polymerization is sensitive to photolysis. There were disadvantages such as inferiority.
一方、アンモニウム塩のボレート誘導体や、ホスホニウム塩のボレート誘導体を利用した光分解性高分子化合物も報告されている（特許文献２）。しかし、この技術は、特殊な化合物を使用するため、コストが高くなったり、また、用途によっては使用が難しいなどの問題があった。 On the other hand, a photodegradable polymer compound using a borate derivative of an ammonium salt or a borate derivative of a phosphonium salt has also been reported (Patent Document 2). However, since this technique uses a special compound, there are problems such as an increase in cost and difficulty in use depending on applications.
従って、本発明は、高分子化合物自体として安定でありながら、光分解感度が優れ、しかも利用しやすい化合物を利用した光分解性高分子化合物の製造方法を提供することをその課題とするものである。 Accordingly, an object of the present invention is to provide a method for producing a photodegradable polymer compound using a compound that is stable as the polymer compound itself but has excellent photolysis sensitivity and is easy to use. is there.
本発明者らは、先にニトロ置換ベンジルを含む基を光分解性部位として利用すれば、それ自体は安定で、かつ、光の作用により容易に分解する光分解性高分子化合物が得られることを見出し、特許出願した（特願２００５−５３４４０）。そして更に、上記光分解性高分子化合物を有利に合成しうる方法について検討を続けた結果、本発明を完成した。 The present inventors can obtain a photodegradable polymer compound that is stable per se and easily decomposes by the action of light if a group containing nitro-substituted benzyl is used as a photodegradable site. And applied for a patent (Japanese Patent Application No. 2005-53440). Furthermore, as a result of continuing investigations on a method that can advantageously synthesize the photodegradable polymer compound, the present invention has been completed.
すなわち本発明は、次の式（Ｉ）
で表される高分子化合物に、開環重合開始剤の存在下、式（II）
で表される環状モノマーを反応させることを特徴とする式（III）
で表される光分解性高分子化合物の製造方法である。
That is, the present invention provides the following formula (I)
In the presence of a ring-opening polymerization initiator, the polymer compound represented by formula (II)
Wherein the cyclic monomer represented by the formula (III) is reacted
This is a method for producing a photodegradable polymer compound represented by the formula:
本発明方法によれば、それ自体は安定で、高感度な光分解性を有する光分解性高分子化合物を得ることができる。 According to the method of the present invention, it is possible to obtain a photodegradable polymer compound that is stable in itself and has high-sensitivity photodegradability.
本発明方法により得られる光分解性高分子化合物は、次の式（VIII）で表される基を光分解性部位として含む点に特徴を有するものである。 The photodegradable polymer compound obtained by the method of the present invention is characterized in that it contains a group represented by the following formula (VIII) as a photodegradable site.
上記の光分解部位（VIII）を含む光分解性高分子化合物は、例えば、１００ｍＷ／ｃｍ２程度の強度の、ＵＶで吸収のある波長の光を、３０秒から１０分間程度の時間照射することにより、上記光分解性部位（VIII）において開裂し、分解する。 For example, the photodegradable polymer compound containing the photodegradation site (VIII) is irradiated with light having a wavelength of UV absorption at an intensity of about 100 mW / cm 2 for about 30 seconds to 10 minutes. To cleave and decompose at the photodegradable site (VIII).
そして、この光分解により分解された高分子化合物の断片には、もとのポリマーの末端であった基、例えば、カルボキシル基、水酸基、アミノ基、スルホニル基等が形成される。 Then, in the fragment of the polymer compound decomposed by this photolysis, a group that is the terminal of the original polymer, for example, a carboxyl group, a hydroxyl group, an amino group, a sulfonyl group, or the like is formed.
なお、上記光分解性部位（VIII）のうち好ましいものとしては、ニトロ基がフェニレン基の２位（ｍ−位）に置換した構造を有するものが挙げられる。 In addition, as a preferable thing among the said photodegradable site | parts (VIII), what has the structure which substituted the nitro group to the 2nd-position (m-position) of a phenylene group is mentioned.
本発明方法により得られる上記式（III）で表される光分解性高分子化合物は、次のようにして製造される。 The photodegradable polymer compound represented by the above formula (III) obtained by the method of the present invention is produced as follows.
（Ａ）化合物（III）の製造：
化合物（III）を製造するには、下式に従い、式（Ｉ）の高分子化合物に、リビング重合開始剤の存在下、式（II）の環状モノマーを反応させればよい。
(A) Production of compound (III):
In order to produce the compound (III), a cyclic monomer of the formula (II) may be reacted with the polymer compound of the formula (I) in the presence of a living polymerization initiator according to the following formula.
出発原料である高分子化合物（Ｉ）は、前出のニトロ置換ベンジル誘導体（Ｖ）と、末端を活性化した高分子化合物とを、常法に従い反応させることにより製造することができる。 The polymer compound (I) as a starting material can be produced by reacting the above-mentioned nitro-substituted benzyl derivative (V) with a polymer compound having an activated terminal according to a conventional method.
また、高分子化合物（Ｉ）と反応させる環状モノマー（II）としては、環状エーテル化合物、環状エステル化合物、環状シロキサン化合物等が挙げられる。このうち、環状エーテル化合物としては、エチレンオキシド、プロピレンオキシド等が、環状エステル化合物としては、β−プロピオラクトン、ラクチド、ε−カプロラクトン等が、環状シロキサン化合物としては、１,１,３,３,５,５−ヘキサメチルトリシロキサン、１,１,３,３,５,５,７,７−オクタメチルテトラシロキサン等が例示される。従って、例えば環状エーテルである場合の、環状モノマー（II）の基Ａおよび基Ｂは、それぞれ開環部分に対応する−ＣＨ２−と−Ｏ−、Ｌは、−（ＣＨ２）ｍ−（ここでｍは任意の整数を意味する）であり、環状エステル化合物（ラクトン類）である場合の基Ａおよび基Ｂは、それぞれ開環部分に対応する−ＣＯ−と−Ｏ−、Ｌは、−（ＣＨ２）ｋ−（ここでｋは任意の整数を意味する）である。 In addition, examples of the cyclic monomer (II) to be reacted with the polymer compound (I) include a cyclic ether compound, a cyclic ester compound, a cyclic siloxane compound, and the like. Among these, as the cyclic ether compound, ethylene oxide, propylene oxide, etc., as the cyclic ester compound, β-propiolactone, lactide, ε-caprolactone, etc., as the cyclic siloxane compound, 1, 1, 3, 3, Examples include 5,5-hexamethyltrisiloxane, 1,1,3,3,5,5,7,7-octamethyltetrasiloxane and the like. Therefore, for example, in the case of a cyclic ether, the group A and the group B of the cyclic monomer (II) are each —CH 2 — and —O— corresponding to the ring-opening moiety, and L is — (CH 2 ) m— ( M represents an arbitrary integer), and in the case of a cyclic ester compound (lactones), the group A and the group B are —CO—, —O—, and L corresponding to the ring-opening moiety, respectively. - a (CH 2) k- (wherein k denotes an arbitrary integer).
この高分子化合物（Ｉ）と環状モノマー（II）との反応は、開環重合開始剤の存在下、トルエン、ＤＭＦ等の溶媒を使用して行われる。この反応は、高分子化合物（Ｉ）を高真空下、溶媒中に加え、更に開環重合開始剤を加えて室温で１時間程度反応させた後、環状モノマー（II）を、５０℃程度の温度で加え、１時間程度反応させれば良い。ここで用いる開環重合開始剤は、開環重合をリビング的に進行させるものであれば、特に限定されない。例えば、環状エーテル化合物のリビング開環重合開始剤としては、ハロゲン化アルミニウムトリフェニルスルホン、ハロゲン化マンガントリフェニルスルホン、アルコキシカリウムなどが挙げられ、環状エステル化合物のリビング開環重合開始剤としては、ジアルキルアルコキシアルミニウム、トリアルコキシアルミニウム、ハロゲン化アルミニウムフェニルスルホンなどが挙げられ、環状シロキサン化合物のリビング開環重合開始剤としては、アルキルリチウム、ハロゲン化アルミニウムトリフェニルスルホンが挙げられる。 The reaction between the polymer compound (I) and the cyclic monomer (II) is performed using a solvent such as toluene or DMF in the presence of a ring-opening polymerization initiator. In this reaction, the polymer compound (I) is added to a solvent under high vacuum, a ring-opening polymerization initiator is further added, and the mixture is allowed to react at room temperature for about 1 hour. What is necessary is just to make it react for about 1 hour, adding at temperature. The ring-opening polymerization initiator used here is not particularly limited as long as the ring-opening polymerization proceeds in a living manner. For example, living ring-opening polymerization initiators for cyclic ether compounds include aluminum halide triphenyl sulfone, halogenated manganese triphenyl sulfone, alkoxy potassium, and the like, and living ring-opening polymerization initiators for cyclic ester compounds include dialkyl. Alkoxyaluminum, trialkoxyaluminum, halogenated aluminum phenylsulfone and the like can be mentioned, and examples of the living ring-opening polymerization initiator of the cyclic siloxane compound include alkyl lithium and aluminum halide triphenylsulfone.
また、式（Ｉ）のＬ１は任意のポリマー鎖であり、特に制約はなく、種々の種類の高分子化合物を利用し製造することができる。その製法は特に制約されないが、分子量や構造の制御の点からリビング重合法により製造されたものであることが好ましい。更に、このリビング重合法は、広範囲のモノマーに適用可能である点や、制御の容易さの点から、原子移動ラジカル重合（Atomic Transfer Radical Polymerization;ATRP）法がより好ましい。 L 1 in the formula (I) is an arbitrary polymer chain, and is not particularly limited, and can be produced using various types of polymer compounds. The production method is not particularly limited, but is preferably produced by a living polymerization method from the viewpoint of control of molecular weight and structure. Furthermore, this living polymerization method is more preferably an atomic transfer radical polymerization (ATRP) method from the viewpoints of being applicable to a wide range of monomers and ease of control.
次に実施例を挙げ、本発明を更に詳しく説明するが、本発明はこれら実施例等により何ら制約されるものではない。 EXAMPLES Next, although an Example is given and this invention is demonstrated in more detail, this invention is not restrict | limited at all by these Examples.
実 施 例 １
ポリスチレン末端の２−ニトロベンジル基（マクロイニシエーター）からのε−カ プロラクトンの重合：
（１）窒素気流下、式（Ａ）で示される末端が臭素で修飾されたポリスチレン（Ｍｎ＝８７７０） １.１４ｇ（０.１３ｍｍｏｌ）と４−ヒドロキシ−５−メトキシ−２−ニトロベンジルアルコール ０.２７ｇ（１.３６ｍｍｏｌ）をＤＭＦ １２ｍｌに溶かし、炭酸カリウム ０.１５９ｇ（１.１５ｍｍｏｌ）を加えて終夜撹拌した。これをメタノールに滴下して反応を停止し、そのままメタノールにて再沈殿を行った。ＴＨＦ／メタノール系で再沈殿を繰り返し、続いてベンゼン溶液から凍結乾燥することで精製し、下式（Ｂ）で示される４−ヒドロキシ−５−メトキシ−２−ニトロベンジルアルコールとポリスチレンの縮合物０.９２４ｇを得た。
Example 1
Polymerization of ε-caprolactone from a polystyrene-terminated 2-nitrobenzyl group (macroinitiator):
(1) 1.14 g (0.13 mmol) of polystyrene modified with bromine at the terminal represented by the formula (A) under a nitrogen stream and 4-hydroxy-5-methoxy-2-nitrobenzyl alcohol 0 .27 g (1.36 mmol) was dissolved in 12 ml of DMF, and 0.159 g (1.15 mmol) of potassium carbonate was added and stirred overnight. This was dropped into methanol to stop the reaction, and reprecipitation was performed with methanol as it was. Purification by repeated reprecipitation in a THF / methanol system, followed by lyophilization from a benzene solution, and a condensate of 4-hydroxy-5-methoxy-2-nitrobenzyl alcohol and polystyrene represented by the following formula (B): Obtained .924 g.
（２）高真空（約１.３３×１０−４ｐａ）下、トルエン中に（１）で得た４−ヒドロキシ−５−メトキシ−２−ニトロベンジルアルコールとポリスチレンの縮合物 ０.４８０ｇ（０.０５４ｍｍｏｌ）とトリエチルアルミニウム ５.２６ｍｇ（０.０６２６ｍｍｏｌ）を加え、室温で一時間程度反応させた。次に、ε−カプロラクトン ０.２１８ｇ（１.９１ｍｍｏｌ）を加え、５０℃で１時間重合を行った。重合は酢酸を入れて停止し、メタノールにて再沈殿を行った。ＴＨＦ／メタノール系で再沈殿を繰り返し、続いてベンゼン溶液から凍結乾燥することで精製し、下式（Ｃ）で表されるポリスチレン部分とポリε−カプロラクトン部分を有する光分解性高分子化合物０.２８２ｇを得た。 (2) Condensate of 4-hydroxy-5-methoxy-2-nitrobenzyl alcohol obtained in (1) and polystyrene in toluene under high vacuum (about 1.33 × 10 −4 pa) 0.480 g (0 0.054 mmol) and 5.26 mg (0.0626 mmol) of triethylaluminum were added and reacted at room temperature for about 1 hour. Next, 0.218 g (1.91 mmol) of ε-caprolactone was added, and polymerization was performed at 50 ° C. for 1 hour. Polymerization was stopped by adding acetic acid, and reprecipitation was performed with methanol. Reprecipitation is repeated in a THF / methanol system, followed by purification by freeze-drying from a benzene solution, and a photodegradable polymer compound having a polystyrene portion and a polyε-caprolactone portion represented by the following formula (C): 282 g was obtained.
実 施 例 ２
実施例１の操作（２）において、４−ヒドロキシー５−メトキシー２−ニトロベンジルアルコールとポリスチレンの縮合物を０.５６９ｇ（０.０６４ｍｍｏｌ）に、トリエチルアルミニウムを７.０６ｍｇ（０.０８４０ｍｍｏｌ）に、ε−カプロラクトンを０.２０２ｇ（１.７７ｍｍｏｌ）にした以外は同様にして、式（Ｃ）で表されるポリスチレン部分とポリε―カプロラクトン部分を有する光分解性高分子化合物０.３７８ｇを得た。
Example 2
In the operation (2) of Example 1, the condensation product of 4-hydroxy-5-methoxy-2-nitrobenzyl alcohol and polystyrene was added to 0.569 g (0.064 mmol), and triethylaluminum was added to 7.06 mg (0.0840 mmol). Except that ε-caprolactone was changed to 0.202 g (1.77 mmol), 0.378 g of a photodegradable polymer compound having a polystyrene portion represented by the formula (C) and a polyε-caprolactone portion was obtained. .
実 施 例 ３
（１）ＡＴＲＰによるスチレンの重合：
室温、窒素気流下において、３０ｍｌニロナスフラスコに、スチレン７.８６ｇ（７５.５ｍｍｏｌ）、（１−ブロモエチル）ベンゼン０.１２５ｇ（０.６８ｍｍｏｌ）、２.２’―ビピリジル０.３２４ｇ（２.０４ｍｍｏｌ）および臭化銅０.０９９ｇ（０.６８ｍｍｏｌ）を入れ、窒素雰囲気下とし、１１０℃で１２時間攪拌した。これを再沈殿（メタノール１００ｍｌ ２回）し、吸引ろ過、真空乾燥し、白色固体として、末端が臭素で修飾されたポリスチレン５.１３ｇを得た。
Example 3
(1) Polymerization of styrene by ATRP:
Under a nitrogen stream at room temperature, 7.86 g (75.5 mmol) of styrene, 0.125 g (0.68 mmol) of (1-bromoethyl) benzene, and 0.324 g of 2.2′-bipyridyl (2. 04 mmol) and 0.099 g (0.68 mmol) of copper bromide were placed in a nitrogen atmosphere and stirred at 110 ° C. for 12 hours. This was re-precipitated (100 ml of methanol twice), suction filtered, and vacuum-dried to obtain 5.13 g of polystyrene having a terminal modified with bromine as a white solid.
（２）光分解性基の導入：
室温、窒素気流下において、２００ｍｌニロナスフラスコに１−（４−ヒドロキシー５−メトキシー２−ニトロフェニル）エタノール０.１５０ｇ（７０４μｍｏｌ）、ＤＭＦ４０ｍｌ、炭酸カリウム０.１８７ｇ（１.３５ｍｍｏｌ）、上記で得た、末端が臭素で修飾されたポリスチレン３.０１ｇ（３３４μｍｏｌ）を入れ、窒素雰囲気下とし、８０℃で終夜攪拌した。これに水１００ｍｌを入れ、抽出（クロロホルム １００ｍｌ、３回）、洗浄（飽和食塩水 １００ｍｌ）し、無水硫酸マグネシウムで乾燥し、濃縮した。これにクロロホルムを少量加え、再沈殿（メタノール ５０ｍｌ、２回）し、吸引ろ過、真空乾燥し、白色固体２.７３ｇを得た。
(2) Introduction of photodegradable group:
Under a nitrogen stream at room temperature, 0.150 g (704 μmol) of 1- (4-hydroxy-5-methoxy-2-nitrophenyl) ethanol, 40 ml of DMF, and 0.187 g (1.35 mmol) of potassium carbonate were obtained in the above. Further, 3.01 g (334 μmol) of polystyrene modified with bromine at the end was added, and the mixture was placed in a nitrogen atmosphere and stirred at 80 ° C. overnight. 100 ml of water was added thereto, extracted (chloroform 100 ml, 3 times), washed (saturated brine 100 ml), dried over anhydrous magnesium sulfate, and concentrated. A small amount of chloroform was added thereto, re-precipitated (50 ml of methanol, twice), suction filtered and vacuum dried to obtain 2.73 g of a white solid.
これをカラムクロマトグラフィー（ヘキサン：酢酸エチル＝２：１）により分離生成し、濃縮後、クロロホルムを少量加え、最沈殿（メタノール３０ｍｌ）し、吸引ろ過、真空乾燥し、白色固体として、末端に光分解性基を導入したポリスチレン０.６８０ｇを得た。 This was separated and produced by column chromatography (hexane: ethyl acetate = 2: 1), concentrated, added with a small amount of chloroform, reprecipitated (30 ml of methanol), suction filtered, vacuum dried, and dried as a white solid. 0.6680 g of polystyrene having a degradable group introduced was obtained.
（３）ポリスチレン末端の２−ニトロベンジル基（マクロイニシエーター）からの
ε―カプロラクトンの重合：
高真空（約１.３３×１０−４ｐａ）下、１.６３ｍｇ（０.００３９１ｍｍｏｌ）の、予め高真空下１時間乾燥後、ＴＨＦで希釈したトリフルオロメタンスルホン酸スズ（II）を反応容器に入れて溶媒を除去した後、上記で得た末端に光分解性基を導入したポリスチレン１９２ｍｇ（０.０２１３ｍｍｏｌ）を加えて室温で１時間置いた。続いて４４２ｍｇ（３.８８ｍｍｏｌ）のε―カプロラクトンを加えて７０℃で４８時間反応させた。反応溶液を２００ｍｌのメタノールに注ぎ込み、沈殿物を回収して２０３ｍｇの淡褐色固体を得た。
(3) Polymerization of ε-caprolactone from 2-nitrobenzyl group (macroinitiator) at the end of polystyrene:
Under high vacuum (about 1.33 × 10 −4 pa), 1.63 mg (0.000039 mmol), dried in advance under high vacuum for 1 hour, and diluted with THF (II) trifluoromethanesulfonate in a reaction vessel. Then, after removing the solvent, 192 mg (0.0213 mmol) of polystyrene having a photodegradable group introduced at the terminal obtained above was added, and the mixture was allowed to stand at room temperature for 1 hour. Subsequently, 442 mg (3.88 mmol) of ε-caprolactone was added and reacted at 70 ° C. for 48 hours. The reaction solution was poured into 200 ml of methanol, and the precipitate was collected to obtain 203 mg of a light brown solid.
試 験 例
上記の実施例で得た光分解性高分子化合物をクロロホルムに溶解後キャストし、約０.１ｍｍ厚のフィルムを得た。このフィルムに超高圧水銀灯（ＵＳＨ−５００Ｄ）にて、硫酸銅フィルターを用いて３２０ｎｍ以上の光を１分間照射した。
Test Example The photodegradable polymer compound obtained in the above Example was dissolved in chloroform and cast to obtain a film having a thickness of about 0.1 mm. This film was irradiated with light of 320 nm or more for 1 minute using an ultrahigh pressure mercury lamp (USH-500D) using a copper sulfate filter.
紫外線照射前後のフィルムのＩＲ（日本分光製 ＦＴ／ＩＲ−４６０ｐｌｕｓ）測定を行ったところ、照射前のフィルムのスペクトルではニトロ基に由来する１５２０ｃｍ−１付近のピークが確認されるのに対し、照射後のフィルムのスペクトルではそのピークが消失していることから、ポリマー間の結合が切断されたことが示唆された。 When IR (FT / IR-460plus manufactured by JASCO Corporation) measurement was performed on the film before and after UV irradiation, a peak near 1520 cm −1 derived from the nitro group was confirmed in the spectrum of the film before irradiation. In the later film spectrum, the peak disappeared, suggesting that the bond between the polymers was broken.
また、紫外線照射前後のフィルムをＴＨＦに溶解し、ＧＰＣ（ＴＯＳＯＨ製 ＨＬＣ−８０２０）測定（溶媒：ＴＨＦ，送液速度：１.０ｍＬ／ｍｉｎ，カラム：Ｇ５０００ＨＸＬ＋ Ｇ４０００ＨＸＬ＋ Ｇ３０００ＨＸＬ）により分子量および分子量分布（標準試料：ポリスチレン）を確認した。この結果、紫外線照射後のサンプルは照射前と比較し、低分子量側にポリスチレンブロックと一致するピークがあり、分解反応が起きていることがわかる。 Further, the film before and after the ultraviolet irradiation was dissolved in THF, and the molecular weight was measured by GPC (HLC-8020 manufactured by TOSOH) measurement (solvent: THF, liquid feed rate: 1.0 mL / min, column: G5000H XL + G4000H XL + G3000H XL ). The molecular weight distribution (standard sample: polystyrene) was confirmed. As a result, it can be seen that the sample after the ultraviolet irradiation has a peak corresponding to the polystyrene block on the low molecular weight side as compared with that before the irradiation, and the decomposition reaction occurs.
本発明方法により得られる光分解性高分子化合物は、通常の使用状態では安定であるが、ＵＶで吸収のある光を照射することにより、容易に分解するものである。 The photodegradable polymer compound obtained by the method of the present invention is stable under normal use conditions, but is easily decomposed by irradiation with UV-absorbing light.
従って、本発明の光分解性高分子化合物でプラスチック製品を製造すれば、使用後に光を照射して分解させ、ポリマーフラグメントを再使用するなど、リサイクルに適した製品を提供することが可能になる。 Therefore, if a plastic product is manufactured using the photodegradable polymer compound of the present invention, it is possible to provide a product suitable for recycling, such as by irradiating light after use and decomposing it, and reusing the polymer fragment. .
また、本発明方法によれば、例えば、ポリスチレン鎖とポリオキシエチレン鎖とが光分解性部分のみを介して結合される光分解性高分子化合物中も得られるが、このものは、経済性、物性とも好ましいものである。 Further, according to the method of the present invention, for example, a photodegradable polymer compound in which a polystyrene chain and a polyoxyethylene chain are bonded only through a photodegradable moiety can be obtained. The physical properties are also preferable.
更に、本発明方法によれば、例えば、ポリスチレン鎖とポリε−カプロラクタムとが光分解性部分のみを介して結合される光分解性高分子化合物中も得られ、新しい物性を有する高分子としての利用も期待される。
以 上
Furthermore, according to the method of the present invention, for example, a photodegradable polymer compound in which a polystyrene chain and polyε-caprolactam are bonded only through a photodegradable moiety can be obtained, and a polymer having a new physical property can be obtained. Use is also expected.
more than
Claims (5)
で表される高分子化合物に、開環重合開始剤の存在下、式（II）
で表される環状エステル化合物を反応させることを特徴とする式（III）
で表される光分解性高分子化合物の製造方法。 The following formula (I)
In the presence of a ring-opening polymerization initiator, the polymer compound represented by formula (II)
A cyclic ester compound represented by the formula (III)
The manufacturing method of the photodegradable polymer compound represented by these.
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