JPH0136841B2 - - Google Patents
Info
- Publication number
- JPH0136841B2 JPH0136841B2 JP4612184A JP4612184A JPH0136841B2 JP H0136841 B2 JPH0136841 B2 JP H0136841B2 JP 4612184 A JP4612184 A JP 4612184A JP 4612184 A JP4612184 A JP 4612184A JP H0136841 B2 JPH0136841 B2 JP H0136841B2
- Authority
- JP
- Japan
- Prior art keywords
- temperature
- cell
- isopropylacrylamide
- water
- membrane
- 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
Links
- 239000012528 membrane Substances 0.000 claims description 33
- 229920002678 cellulose Polymers 0.000 claims description 24
- 239000001913 cellulose Substances 0.000 claims description 24
- XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 claims description 14
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 13
- 238000010559 graft polymerization reaction Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- 239000010408 film Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 229910001873 dinitrogen Inorganic materials 0.000 description 6
- 229920002379 silicone rubber Polymers 0.000 description 5
- 239000004945 silicone rubber Substances 0.000 description 5
- 230000035699 permeability Effects 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000002131 composite material Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229920002432 poly(vinyl methyl ether) polymer Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Landscapes
- Graft Or Block Polymers (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Description
【発明の詳細な説明】
本発明は、セルロース膜の片面にＮ―イソプロ
ピルアクリルアミドをグラフト重合させた感温性
フイルム材料とその製造方法に関するものであ
る。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a temperature-sensitive film material in which N-isopropylacrylamide is graft-polymerized on one side of a cellulose membrane, and a method for producing the same.
ポリＮ―イソプロピルアクリルアミド、ポリビ
ニルメチルエーテルなどのいわゆる熱可逆高分子
は、通常の水溶性高分子とは逆に低温で水に溶解
し、高温では疎水化析出するという特異な可逆的
溶解特性を示し、遮光体や水性接着剤等、広範な
分野への応用が期待されている。たとえば、これ
ら熱可逆高分子を水溶液状態で２枚のガラス板の
間に封入すれば、これは高温で白濁し、温度調節
機能を有する遮光体として温室の天窓等に利用し
うる。 So-called thermoreversible polymers such as polyN-isopropylacrylamide and polyvinyl methyl ether exhibit unique reversible dissolution characteristics, in that they dissolve in water at low temperatures and precipitate as hydrophobes at high temperatures, contrary to ordinary water-soluble polymers. It is expected to be applied to a wide range of fields, including light shielding materials and water-based adhesives. For example, if these thermoreversible polymers are sealed between two glass plates in an aqueous solution state, they will become cloudy at high temperatures and can be used as a light shielding material with a temperature regulating function in skylights of greenhouses and the like.
しかしながら、熱可逆高分子は一種の感温性素
材であり、したがつてこれを何らかの形でフイル
ム状に成形すれば、上記の天窓はもちろん感温性
をもつ物質分離用透過膜として応用することも可
能となる。本発明者は、このような観点から鋭意
研究を続け、Ｎ―イソプロピルアクリルアミドを
片面にグラフト重合したセルロースフイルムが、
熱可逆的な感温性を有する事実を見出し、本発明
をなすにいたつた。 However, thermoreversible polymer is a type of temperature-sensitive material, so if it is formed into a film in some way, it can be applied not only to the above-mentioned skylight but also as a temperature-sensitive permeable membrane for separating substances. is also possible. The present inventor has continued to conduct intensive research from this perspective, and has discovered that a cellulose film in which N-isopropylacrylamide is graft-polymerized on one side,
The present invention was based on the discovery of thermoreversible temperature sensitivity.
セルロース素材にグラフトしたポリＮ―イソピ
ルアクリルアミドは、単独のポリマーの場合と類
似の熱可逆的挙動を示すことはすでに知られてい
るが、本発明では、セルロース膜の片面にのみ、
Ｎ―イソプロピルアクリルアミドをグラフトさ
せ、感温性遮光体として機能すると同時に、水溶
液における感温性の物質透過膜としても機能しう
る材料とした点に特徴がある。 Although it is already known that poly N-isopylacrylamide grafted onto a cellulose material exhibits thermoreversible behavior similar to that of the polymer alone, in the present invention, poly N-isopylacrylamide is grafted onto only one side of the cellulose membrane.
The material is grafted with N-isopropylacrylamide and functions as a temperature-sensitive light-shielding material, as well as a material that can function as a temperature-sensitive material-permeable membrane in an aqueous solution.
物質透過性の異なる２枚の薄膜からなる複合膜
は、水溶液中で、濃度や温度に応じ、特異な物質
透過性を示すことが知られているが、本発明の感
温性フイルム材料からなる物質透過膜は、セルロ
ース基材とその片面のグラフトポリＮ―イソプロ
ピルアクリルアミドというまつたく性質の異なる
２種の高分子材料で形成された複合膜となつてお
り、ポリＮ―イソプロピルアクリルアミドは低温
域においても、水中に溶解散逸することなく、セ
ルロース膜の片面に固定化されて物質透過の調整
機能を発揮する。 It is known that a composite membrane consisting of two thin films with different substance permeability exhibits a unique substance permeability depending on the concentration and temperature in an aqueous solution. The material-permeable membrane is a composite membrane made of two polymeric materials with different properties: a cellulose base material and grafted polyN-isopropylacrylamide on one side. , it is immobilized on one side of the cellulose membrane without dissolving or escaping in water, and exerts the function of regulating substance permeation.
本発明の感温性フイルム材料は以下の操作によ
つて製造される。第１図のごとき真中をセルロー
ス膜で仕切られたジヤケツト１７，１８つきの反
応装置１を用意し、一方のセル２にＮ―イソプロ
ピルアクリルアミド水溶液と硝酸第二セリウムア
ンモニウム塩（重合開始剤）、もう一方のセル３
には、Ｎ―イソプロピルアクリルアミド水溶液の
みをそれぞれ所定量投入し、循環温水１０，１１
で系を一定温度に保ち、マグネチツクスターラー
でセル内を充分かきまぜつつ窒素雰囲気下でセル
２側からセルロース膜に、Ｎ―イソプロピルアク
リルアミドをグラフト重合させる。 The temperature-sensitive film material of the present invention is manufactured by the following operation. A reactor 1 with jackets 17 and 18 partitioned in the middle by a cellulose membrane as shown in Fig. 1 is prepared, one cell 2 contains an aqueous N-isopropylacrylamide solution and ceric ammonium nitrate (polymerization initiator), and the other cell cell 3
In each case, only a predetermined amount of N-isopropylacrylamide aqueous solution was added, and circulating hot water 10 and 11 was added.
The system was kept at a constant temperature, and N-isopropylacrylamide was graft-polymerized from the cell 2 side to the cellulose membrane under a nitrogen atmosphere while thoroughly stirring the inside of the cell with a magnetic stirrer.
基材となるセルロース膜はいかなる種類のもの
でもよいが物質透過の点からは薄いものほどよく
強度の点からは厚いものほどよい。一般には厚さ
0.1mm程度のセルロース膜が好適である。 The cellulose membrane serving as the base material may be of any type, but the thinner it is from the viewpoint of substance permeation, the thicker it is from the viewpoint of strength. generally the thickness
A cellulose membrane of about 0.1 mm is suitable.
Ｎ―イソプロピルアクリルアミドの濃度、硝酸
第二セリウムアンモニウム（重合開始剤）の濃
度、反応温度等Ｎ―イソプロピルアクリルアミド
をセルロース膜にグラフト重合させるための条件
に特に制限はない。 There are no particular limitations on the conditions for graft polymerizing N-isopropylacrylamide onto the cellulose membrane, such as the concentration of N-isopropylacrylamide, the concentration of ceric ammonium nitrate (polymerization initiator), and the reaction temperature.
反応時間についても、Ｎ―イソプロピルアクリ
ルアミドの濃度、硝酸第二セリウムアンモニウム
の濃度、反応温度の組合せにより異なるが、特に
制限はない。 The reaction time also varies depending on the combination of the concentration of N-isopropylacrylamide, the concentration of ceric ammonium nitrate, and the reaction temperature, but is not particularly limited.
なお、このようなグラフト重合は、窒素雰囲気
下で行うことが肝要であり、第１図の反応装置１
においては、セル２、セル３のシリコンゴム栓
４，５にはそれぞれ２つの孔があけられ、ここか
らシリコンゴムチユーブ６，７および８，９を通
して、窒素ガスが流通するようになつている。送
入すべき窒素ガス量については特に制限はない
が、多量の窒素ガスを送入すると、反応液中に多
量の気泡が浮遊し、グラフト重合すべきセルロー
ス膜の表面に、これら気泡が付着して、均一なグ
ラフト重合を妨げる場合があり、この点に留意す
る必要がある。 It is important to carry out such graft polymerization under a nitrogen atmosphere, and the reaction apparatus 1 shown in FIG.
In this case, two holes are formed in the silicone rubber stoppers 4 and 5 of the cells 2 and 3, respectively, from which nitrogen gas flows through silicone rubber tubes 6 and 7 and 8 and 9. There is no particular limit on the amount of nitrogen gas to be introduced, but if a large amount of nitrogen gas is introduced, a large amount of air bubbles will float in the reaction solution, and these air bubbles will adhere to the surface of the cellulose membrane to be graft-polymerized. This may impede uniform graft polymerization, so this point must be kept in mind.
所定時間での反応終結後は、セル２、セル３の
内容液をとり出し、生成グラフトセルロース膜を
充分水洗して水中に保存する。 After the reaction is completed in a predetermined time, the contents of cells 2 and 3 are taken out, and the resulting grafted cellulose membrane is thoroughly washed with water and stored in water.
上記のごとく製造された感温性フイルムは、た
とえば以下のように物質分離用透過膜として応用
しうる。 The temperature-sensitive film produced as described above can be applied, for example, as a permeable membrane for separating substances as described below.
生成グラフトセルロース膜を反応装置１に固定
したまま水洗し、さらにセル２、セル３に水を満
して、１、２日枚置する。水をとりだした後、所
定温度の循環温水１０，１１を通し、たとえば、
セル２側に同所定温度のアルコール水溶液、セル
３側に同所定温度の水を入れ、セル２からセル３
へアルコールを透過させて、セル３におけるアル
コール濃度の変化を測定する。このアルコール濃
度の変化速度が、膜の物質透過率を表わしてい
る。 The resulting grafted cellulose membrane is washed with water while being fixed in the reaction apparatus 1, and cells 2 and 3 are further filled with water and left for 1 or 2 days. After taking out the water, circulate hot water 10, 11 at a predetermined temperature is passed through, for example,
Fill the cell 2 side with an alcohol aqueous solution at the same predetermined temperature, and the cell 3 side with water at the same predetermined temperature, and then move from cell 2 to cell 3.
The change in alcohol concentration in the cell 3 is measured. The rate of change in alcohol concentration represents the substance permeability of the membrane.
以下実施例によつて、発明をより詳細に説明す
る。 The invention will be explained in more detail with reference to Examples below.
実施例
まずあらかじめ、10重量％のＮ―イソプロピル
アクリルアミド水溶液および硝酸第二セリウムア
ンモニウム3.38ｇ、硝酸14mlに水を加え計250ml
とした濃度25mmol／の硝酸第二セリウムアン
モニウム水溶液を用意する。Example First, water was added to a 10% by weight aqueous solution of N-isopropylacrylamide, 3.38 g of ceric ammonium nitrate, and 14 ml of nitric acid for a total of 250 ml.
Prepare an aqueous solution of ceric ammonium nitrate with a concentration of 25 mmol/.
セル２，３の容量が120ml、接合部１９の直径
22mmである第１図と同形の反応装置１を用意し、
止金１６およびシリコンゴムパツキン１４，１５
によつて接合部に市販キユプロフアン膜（西ドイ
ツENKA社製）を設置する。 Capacity of cells 2 and 3 is 120ml, diameter of joint 19
Prepare a reactor 1 of the same shape as in Fig. 1, which is 22 mm,
Clasp 16 and silicone rubber gaskets 14, 15
A commercially available Kyuprofan membrane (manufactured by ENKA, West Germany) is installed at the joint.
次いでセル２側に前記のＮ―イソプロピルアク
リルアミド水溶液を80ml、セル３側に同溶液を90
ml投入し、マグネチツクスターラー１２，１３を
回転させつつ約10分間両セルに25℃の循環温水を
流し、同時に窒素ガスを送入する。 Next, add 80 ml of the above N-isopropylacrylamide aqueous solution to the cell 2 side, and 90 ml of the same solution to the cell 3 side.
ml, and while rotating the magnetic stirrers 12 and 13, circulated hot water at 25°C was flowed through both cells for about 10 minutes, and at the same time nitrogen gas was introduced.
準備完了後セル２側に、前記硝酸第二セリウム
アンモニウム水溶液10mlを投入しセルロース膜表
面に対するグラフト重合反応を開始させる。２時
間ないし３時間の反応終結後、セル２，３に水を
投入して水洗をくり返し、さらにセル２，３に水
を満たした状態で、40℃および25℃の温水を循環
させる。セル２，３内が40℃の状態では、生成グ
ラフトセルロース膜は白濁し、25℃の状態では半
透明となつて感温性を示すことが確認された。 After completion of preparation, 10 ml of the above ceric ammonium nitrate aqueous solution is introduced into the cell 2 side to start a graft polymerization reaction on the cellulose membrane surface. After completion of the reaction for 2 to 3 hours, water is poured into cells 2 and 3 to repeat the washing process, and hot water at 40° C. and 25° C. is circulated while cells 2 and 3 are filled with water. It was confirmed that when the temperature inside Cells 2 and 3 was 40°C, the resulting grafted cellulose membrane became cloudy, and when the temperature was 25°C, it became translucent and exhibited temperature sensitivity.
参考例
前記実施例、で得られた生成グラフトセルロー
ス膜を実施例の反応装置１に固定したままセル
２，３に水を投入し、循環温水で、反応装置を所
定温度に保つ。セル２，３内の水をとり出し、別
に用意された同一所定温度の10％メタノール溶液
100mlをセル２に、水100mlをセル３に投入し、マ
グネチツクスターラーを回転させて、グラフトセ
ルロース膜を透過してセル２からセル３へ移行す
るメタノールの量を所定時間ごとに測定する。移
行メタノール量は、セル３におけるメタノールの
濃度の変化を示差屈折計で測定することにより、
求める。Reference Example While the grafted cellulose membrane obtained in the above example is fixed in the reaction apparatus 1 of the example, water is introduced into cells 2 and 3, and the reaction apparatus is maintained at a predetermined temperature with circulating hot water. Take out the water in cells 2 and 3 and add a separately prepared 10% methanol solution at the same predetermined temperature.
Pour 100 ml of water into cell 2 and 100 ml of water into cell 3, rotate the magnetic stirrer, and measure the amount of methanol that passes through the grafted cellulose membrane and transfers from cell 2 to cell 3 at predetermined intervals. The amount of migrated methanol can be determined by measuring the change in methanol concentration in cell 3 using a differential refractometer.
demand.
第２図はその結果を示すものであり、横軸は測
定温度、縦軸は透過開始200分後のセル３におけ
るメタノール濃度（示差屈折計の目盛であらわ
す）である。 FIG. 2 shows the results, where the horizontal axis is the measured temperature and the vertical axis is the methanol concentration (expressed on the scale of the differential refractometer) in the cell 3 200 minutes after the start of transmission.
これをみると未処理セルロース膜(A)のメタノー
ル透過特性は、温度に対して直線的に変化してい
るが、実施例で得られたＮ―イソプロピルアクリ
ルアミドグラフト膜は、グラフト反応時間２時間
の膜(B)、グラフト反応時間３時間の膜(C)とも温度
に対するメタノール透過特性が直線的でなく、特
にＣでは未処理セルロース膜とは著しく異なつた
感温的な透過特性を示すことが認められる。 This shows that the methanol permeation characteristics of the untreated cellulose membrane (A) change linearly with temperature, but the N-isopropylacrylamide graft membrane obtained in the example shows that the methanol permeability characteristics of the untreated cellulose membrane (A) change linearly with temperature. It was observed that the methanol permeation characteristics with respect to temperature were not linear for both the membrane (B) and the membrane with a grafting reaction time of 3 hours (C), and in particular, C exhibited temperature-sensitive permeation characteristics that were significantly different from that of the untreated cellulose membrane. It will be done.
第１図は本発明の感温性フイルム製造のための
実施例を示す反応装置の全体図であり、第２図参
考例に示すは感温性フイルムからなる物質分離用
透過膜のメタノールの透過特性を示す図である。
１……反応装置、２３……ガラスセル、４，５
……シリコンゴム栓、６，９……窒素ガス流入
管、７，８……窒素ガス流出管、１０，１１……
循環温水経路、１２，１３……マグネチツクスタ
ーラー、１４，１５……シリコンゴムパツキン、
１６……止金、１７，１８……ジヤケツト、１９
……接合部、２０……セルロース膜。
Figure 1 is an overall view of a reaction apparatus showing an embodiment for producing a temperature-sensitive film of the present invention, and Figure 2, a reference example, shows the permeation of methanol through a permeable membrane for substance separation made of a temperature-sensitive film. FIG. 3 is a diagram showing characteristics. 1...Reactor, 23...Glass cell, 4,5
...Silicone rubber stopper, 6,9...Nitrogen gas inflow pipe, 7,8...Nitrogen gas outflow pipe, 10,11...
Circulating hot water path, 12, 13...Magnetic stirrer, 14, 15...Silicone rubber gasket,
16... Clasp, 17, 18... Jacket, 19
. . . Joint portion, 20 . . . Cellulose membrane.
Claims (1)
リルアミドをグラフト重合させたことを特徴とす
る感温性フイルム材料。 ２ セルロース膜をＮ―イソプロピルアクリルア
ミド水溶液中に浸漬し、その一方の面側にのみ硝
酸第二セリウムアンモニウム塩を存在させてグラ
フト重合を行わせることを特徴とする感温性フイ
ルムの製造方法。[Claims] 1. A temperature-sensitive film material characterized in that N-isopropylacrylamide is graft-polymerized on one side of a cellulose membrane. 2. A method for producing a temperature-sensitive film, which comprises immersing a cellulose membrane in an aqueous N-isopropylacrylamide solution and performing graft polymerization in the presence of ceric ammonium nitrate only on one side.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4612184A JPS60188411A (en) | 1984-03-09 | 1984-03-09 | Temperature-sensitive film material and its production |
| JP18320688A JPS6458303A (en) | 1984-03-09 | 1988-07-22 | Permeably separating membrane consisting of temperature sensitive film material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4612184A JPS60188411A (en) | 1984-03-09 | 1984-03-09 | Temperature-sensitive film material and its production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60188411A JPS60188411A (en) | 1985-09-25 |
| JPH0136841B2 true JPH0136841B2 (en) | 1989-08-02 |
Family
ID=12738155
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4612184A Granted JPS60188411A (en) | 1984-03-09 | 1984-03-09 | Temperature-sensitive film material and its production |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60188411A (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8536266B2 (en) | 2011-12-21 | 2013-09-17 | The Goodyear Tire & Rubber Company | Pneumatic tire |
| US9133310B2 (en) | 2011-12-21 | 2015-09-15 | The Goodyear Tire & Rubber Company | Graft copolymer |
| US8759451B2 (en) | 2011-12-21 | 2014-06-24 | The Goodyear Tire & Rubber Company | Method of making a graft copolymer |
| US9156932B2 (en) | 2011-12-21 | 2015-10-13 | The Goodyear Tire & Rubber Company | Method of making a graft copolymer |
| US8415432B1 (en) | 2011-12-21 | 2013-04-09 | The Goodyear Tire & Rubber Company | Rubber composition and pneumatic tire |
| US8563656B1 (en) | 2012-11-08 | 2013-10-22 | The Goodyear Tire & Rubber Company | Method to improve green strength in elastomers |
| US9133333B2 (en) | 2012-11-27 | 2015-09-15 | The Goodyear Tire & Rubber Company | Blend of a graft copolymer and a second polymer miscible with sidechains of the graft copolymer |
| US8883884B2 (en) | 2012-11-27 | 2014-11-11 | The Goodyear Tire & Rubber Company | Pneumatic tire |
| CN106492660B (en) * | 2015-09-08 | 2020-01-03 | 天津工业大学 | Temperature response PVDF semi-interpenetrating network polymer film and preparation method thereof |
-
1984
- 1984-03-09 JP JP4612184A patent/JPS60188411A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60188411A (en) | 1985-09-25 |
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