JPS6048543B2 - Hydrophilic-hydrophobic thermoreversible materials - Google Patents
Hydrophilic-hydrophobic thermoreversible materialsInfo
- Publication number
- JPS6048543B2 JPS6048543B2 JP5455082A JP5455082A JPS6048543B2 JP S6048543 B2 JPS6048543 B2 JP S6048543B2 JP 5455082 A JP5455082 A JP 5455082A JP 5455082 A JP5455082 A JP 5455082A JP S6048543 B2 JPS6048543 B2 JP S6048543B2
- Authority
- JP
- Japan
- Prior art keywords
- temperature
- hydrophilic
- propylacrylamide
- aqueous solution
- materials
- 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
- 239000000463 material Substances 0.000 title claims description 19
- 239000007864 aqueous solution Substances 0.000 claims description 13
- -1 poly(N-n-propylacrylamide) Polymers 0.000 claims description 12
- 230000007704 transition Effects 0.000 claims description 8
- 230000002209 hydrophobic effect Effects 0.000 claims description 2
- 150000002433 hydrophilic molecules Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- WDFKEEALECCKTJ-UHFFFAOYSA-N n-propylprop-2-enamide Chemical compound CCCNC(=O)C=C WDFKEEALECCKTJ-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- YQIGLEFUZMIVHU-UHFFFAOYSA-N 2-methyl-n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C(C)=C YQIGLEFUZMIVHU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000017 hydrogel Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000003094 microcapsule Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- QNILTEGFHQSKFF-UHFFFAOYSA-N n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=C QNILTEGFHQSKFF-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- GUTLYIVDDKVIGB-OUBTZVSYSA-N Cobalt-60 Chemical compound [60Co] GUTLYIVDDKVIGB-OUBTZVSYSA-N 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 206010027175 memory impairment Diseases 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 238000009849 vacuum degassing Methods 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Description
【発明の詳細な説明】
本発明は、新規な親水性−疎水性熱可逆型材料に関す
るものてある。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel hydrophilic-hydrophobic thermoreversible material.
温室、フレームハウス、シヨウウインドウなどの透明
壁や住居、工場の明り取り用天窓などは、夏期の炎天下
には必要以上に内部の温度を上昇させることがあるので
、このような場合にはなんらかの手段て直射日光を遮る
ことが必要になる。Transparent walls such as greenhouses, frame houses, and window windows, as well as skylights for lighting in residences and factories, can cause the internal temperature to rise more than necessary under the scorching sun in summer, so in such cases, take some measures. It is necessary to block direct sunlight.
これまで、このような遮光手段としては、カーテン、ス
ダレ、ブラインドなどの遮光体で所定の透明部分を覆い
、直射日光から内部を遮ることが行われていた。 しか
しながら、このような方法では、遮光が必要か否かを判
断した上、その都度遮光体を取り付けたり取りはずした
りしなければならないというわずらしさがある。Hitherto, such light shielding means has been carried out by covering a predetermined transparent portion with a light shielding body such as a curtain, blind, or blind to shield the interior from direct sunlight. However, such a method is cumbersome in that it must be determined whether or not light shielding is necessary, and then the light shield must be attached or removed each time.
したがつて、太陽光が弱い場合には光をよく透過するが
、必要以上に太陽光が強くなり内部温度が上昇したとき
には、これを透過しなくなるような感温性材料で透明部
分を形成させれは、上記のようなわすられしさを無くす
ことができる。 本発明者は、このような要求を満たす
材料を開発すべく種々研究を重ね、先にＮ−イソプロピ
ルアクリルアミド又はＮ−イソプロピルメタクリルアミ
ドの重合体は、ある温度以下では親水性であり、その水
溶液は透明であるが、その温度よりも高くなると疎水性
に変わり、不透明化する性質を有することを見出し、こ
の性質を利用して遮光材料とすることを提案した。Therefore, when the sunlight is weak, the transparent part is formed with a temperature-sensitive material that transmits light well, but when the sunlight becomes stronger than necessary and the internal temperature rises, it stops transmitting it. This can eliminate the forgetfulness mentioned above. The present inventor has conducted various studies to develop materials that meet these requirements, and first discovered that the polymer of N-isopropylacrylamide or N-isopropylmethacrylamide is hydrophilic below a certain temperature, and its aqueous solution is Although it is transparent, it has been found that it becomes hydrophobic and becomes opaque when the temperature rises above that temperature, and it was proposed to utilize this property to make it into a light-shielding material.
しかしながら、このＮ−イソプロピルアクリルアミド
又はＮ−イソプロピルメタクリルアミドの重合体は、そ
の親水性と疎水性との転移温度が約２９〜４４０Ｃと高
いためその利用範囲がかなり制限されるのを免れない。However, since the polymer of N-isopropylacrylamide or N-isopropylmethacrylamide has a high transition temperature between hydrophilicity and hydrophobicity of about 29 to 440C, its range of use is inevitably limited.
本発明者らは、さらに低い転移温度をもち、より利用
範囲の拡大された材料を開発すへく研究を続けた結果、
ポリ （Ｎ−ｎ−プロピルアクリルアミド）が、親水性
と疎水性との転移温度が１６〜１９０Ｃと低く、従来の
ものよりもはるかに有用な感温性材料を構成しうること
を見出し、この知見に基づいて本発明をなすに至つた。
すなわち、本発明はＮ−（ｎ−プロピルアクリルアミ
ド）の水溶液から実質的に成る転移温度１６〜１９０Ｃ
をもつ親水性−疎水性熱可逆型材料を提供するものであ
る。 本発明で用いられるＮ−（ｎ−プロピルアクリル
アミド）は、例えばＮ−ｎ−プロピルアクリルアミドを
単独でもしくは適当な溶剤に溶かし、放射線を照射する
か、あるいはラジカル重合開始剤の存在下で加熱するこ
とにより製造される。As a result of continued research to develop a material with an even lower transition temperature and a wider range of applications, the present inventors found that
We discovered that poly(N-n-propylacrylamide) has a low transition temperature between hydrophilicity and hydrophobicity of 16 to 190C, and can constitute a much more useful temperature-sensitive material than conventional materials. The present invention was made based on this.
That is, the present invention consists essentially of an aqueous solution of N-(n-propylacrylamide) with a transition temperature of 16 to 190C.
The present invention provides a hydrophilic-hydrophobic thermoreversible material having the following characteristics. N-(n-propylacrylamide) used in the present invention can be produced by, for example, N-n-propylacrylamide alone or dissolved in a suitable solvent and irradiated with radiation or heated in the presence of a radical polymerization initiator. Manufactured by.
このものは１６〜１９０Ｃの温度て可逆的に親水性−疎
水性の転移を行い、その水溶液中での示差走査熱量測定
において１６．５℃で吸熱ピークを示すという特徴を有
している。また、３０゜Ｃにおける極限粘度は０．０１
〜６．０）好ましくは０．１〜３．０の範囲てある。本
発明の親水性−疎水性熱可逆型材料は、ポリ（Ｎ−ｎ−
プロピルアクリルアミド）を、水溶液のような水との組
成物の形に調製する必要がある。この際の濃度は使用目
的に応じて変わるが、通常０．０５〜１０重量％の範囲
で選ばれる。このようにして調製された親水性−疎水性
熱可逆型材料は、その光透過についての温度可逆性を利
用して、遮光材料、水溶性接着剤、被覆材料、なつ染剤
などとして広範囲に利用される。例えＪば、本発明の親
水性−疎水性熱可逆型材料は、水溶液のままで、あるい
は含水ゲルやマイクロカプセルの形態で透明板状体に積
層される。この際に用いられる透明板状体の材料として
は、所望の用途に耐えうる強度を有するものてあれば特
に制限はなく、ガラス、プラスチック等これまで透明壁
、窓などに使用されてきた材料の中から任意に選択する
ことができる。この透明板状体に前記組成物を積層させ
る方法としては、例えは水溶液や含水ゲルの場合は２枚
の透明板状体の間にこれを封入する方法、マイクロカプ
セルの場合は適当なバインダーで透明板状体の表面に塗
布する方法などがある。This material undergoes a reversible hydrophilic-hydrophobic transition at a temperature of 16 to 190C, and exhibits an endothermic peak at 16.5C in differential scanning calorimetry in an aqueous solution. Also, the intrinsic viscosity at 30°C is 0.01
~6.0) Preferably in the range of 0.1 to 3.0. The hydrophilic-hydrophobic thermoreversible material of the present invention is a poly(N-n-
Propylacrylamide) needs to be prepared in a composition with water, such as an aqueous solution. The concentration at this time varies depending on the purpose of use, but is usually selected in the range of 0.05 to 10% by weight. The hydrophilic-hydrophobic thermoreversible materials prepared in this way are widely used as light-shielding materials, water-soluble adhesives, coating materials, summer dyes, etc. by taking advantage of their temperature-reversible properties regarding light transmission. be done. For example, the hydrophilic-hydrophobic thermoreversible material of the present invention can be laminated on a transparent plate-like body in the form of an aqueous solution or in the form of a hydrogel or microcapsule. There are no particular restrictions on the material for the transparent plate-like body used in this case, as long as it has enough strength to withstand the desired use, and materials that have been used for transparent walls, windows, etc. Any one can be selected from among them. The composition can be laminated on this transparent plate-like body, for example, in the case of an aqueous solution or hydrogel, by sealing it between two transparent plate-like bodies, or in the case of microcapsules, using a suitable binder. There is a method of coating the surface of a transparent plate.
このようにして得られた遮光材料は、例えば太陽直射光
によつて必要以上に室内温度が昇温する−のを自動的に
防止するための透明材料として好適てある。The light-shielding material thus obtained is suitable as a transparent material for automatically preventing the indoor temperature from increasing more than necessary due to direct sunlight, for example.
次に実施例によつて本発明をさらに詳細に説明する。Next, the present invention will be explained in more detail with reference to Examples.
参考例
１１容のΞ角フラスコにトリエチルアミン５８．９ｍＬ
，．ｎ−プロピルアミン（ＣＨ３ＣＨ２ＣＨ２ＮＨ２）
２５．６ｙ及びベンゼン３５０ｍ１を入れ、フラスコを
氷て冷やして内容液を１０’Ｃ以下の温度に保ち、かき
まぜながら、この中にアクリル酸クロリド３５ｍ１と町
ベンゼン１６５ｍιとの準合溶液を滴下漏斗から約３時
間かけてゆつくり滴下した。Reference Example 1 58.9 mL of triethylamine in an 11-volume O-angle flask
、． n-propylamine (CH3CH2CH2NH2)
Add 25.6y and 350ml of benzene, cool the flask with ice to keep the content below 10'C, and while stirring, add a semi-combined solution of 35ml of acrylic acid chloride and 165ml of benzene from the dropping funnel. It was slowly dripped over about 3 hours.
滴下完了後、反応液を冷蔵庫の中に入れ１昼夜放置冷却
したのち、ろ過し、ろ液をロータリーエバポレーターを
用いてベンゼンを留去濃縮した。次いで、減圧蒸留し−
．ｌて沸点１０２’Ｃ／１ｗｕｒＬＨｇの留分を回収し
、無色透明の液体４０ダを得た。このマススペクトルで
は、親ピークが１１３でＮ−ｎ−プロピルアクリルアミ
ドの分子量と一致し、物質が確認された。実施例
参考例で得たＮ−ｎ−プロピルアクリルアミド５ｍ１及
びアセトン１５ｍ１をアンプルに入れ、液体窒素を用い
て減圧脱気を行ない空気を除いたのち、上部をバーナー
で封じた。After completion of the dropwise addition, the reaction solution was placed in a refrigerator and cooled for one day and night, then filtered, and the filtrate was concentrated to remove benzene using a rotary evaporator. Then, distilled under reduced pressure.
．． A fraction with a boiling point of 102'C/1wurLHg was collected to obtain 40 dah of a colorless and transparent liquid. In this mass spectrum, the parent peak was 113, which matched the molecular weight of Nn-propylacrylamide, and the substance was confirmed. 5 ml of N-n-propylacrylamide obtained in Reference Example and 15 ml of acetone were placed in an ampoule, and after vacuum degassing was performed using liquid nitrogen to remove air, the upper part was sealed with a burner.
これに、コバルト６０からのγ線を、温度２８℃でかつ
４．５×１０’Ｒ１Ｈｒの照射量で４０．時間照射して
重合を行わせた。次いでアンプル中の反応液をジエチル
エーテル中に投入し、ポリＮ−ｎ−プロピルアクリルア
ミドを析出沈殿させ、単離して２．５ｇのポリマーを得
た。得られたポリマーをウベローデ粘度計を用いて３０
℃の温度で粘度測定した結果、その極限粘度〔η〕は０
．２０てあつた。得られたポリ （Ｎ−ｎ−プロピルア
クリルアミド）を水に溶解して１重量％水溶液を調製し
、この水溶液を昇温速度１℃Ｉｍｉｎで昇温させながら
分光光度計を用いて５００ｎｒｒＬ，の光透過率を測定
し、その水溶液の温度と光透過率との関係を求めた。To this, gamma rays from cobalt 60 were applied at a temperature of 28°C and an irradiation dose of 4.5 x 10'R1Hr for 40. Polymerization was carried out by irradiation for a certain period of time. Next, the reaction solution in the ampoule was poured into diethyl ether, and polyN-n-propylacrylamide was precipitated and isolated to obtain 2.5 g of polymer. The obtained polymer was measured using an Ubbelohde viscometer at 30
As a result of measuring the viscosity at a temperature of °C, the intrinsic viscosity [η] is 0.
．． It was hot. The obtained poly(N-n-propylacrylamide) was dissolved in water to prepare a 1% by weight aqueous solution, and this aqueous solution was exposed to 500 nrrL of light using a spectrophotometer while heating at a temperature increase rate of 1°C Imin. The transmittance was measured and the relationship between the temperature of the aqueous solution and the light transmittance was determined.
この結果をグラフとして第１図に示す。このグラフから
明らかなように、水溶液中のポリ （Ｎ−ｎ−プロピル
アクリルアミド）は低温域では溶解しているが、１７゜
Ｃより析出しはじめ昇温とともに急激に析出量が増大し
、１９゜Ｃでは光透過率がｏとなり水に不溶となること
がわかる。また、ポリ （Ｎ−ｎ−プロピルアクリルア
ミド）４．０ｍｇ及び水１１．５ｍｇをアルミニウム製
密封容器に入れ、密封セルの蓋をかぶせてサンプルシー
ラーで密封した。試料を示差走査熱量計を用いて、昇温
速度１℃Ｉｍｉｎて熱量測定し、この結果を第２図に示
す。これをみると、吸熱ピークは温度約１０’Ｃよりは
じまり約２３゜Ｃまでブ上一ドな曲線がえがかれている
。この吸熱ピークのピークトップの温度を求めると１６
．５℃てあつた。また、試料の吸熱ピークの面積より転
移熱量（ΔＨ）を求めると８．５２ｃａ１Ｉダであつた
。測定した光透過率及び示差走査熱量より、ポリ（Ｎ−
ｎ−プロピルアクリルアミド）水溶液は、１６〜１８゜
Ｃに転移温度を有することがわかる。The results are shown in FIG. 1 as a graph. As is clear from this graph, poly(N-n-propylacrylamide) in an aqueous solution dissolves at low temperatures, but begins to precipitate at 17°C, and the amount of precipitation increases rapidly as the temperature rises. It can be seen that C has a light transmittance of o and is insoluble in water. Further, 4.0 mg of poly(N-n-propylacrylamide) and 11.5 mg of water were placed in an aluminum sealed container, which was covered with a sealed cell lid and sealed with a sample sealer. The sample was subjected to calorimetric measurement using a differential scanning calorimeter at a heating rate of 1° C. Imin, and the results are shown in FIG. Looking at this, the endothermic peak begins at a temperature of about 10'C and shows a uniform curve up to about 23°C. The temperature at the top of this endothermic peak is found to be 16
．． It was 5 degrees Celsius. Further, the amount of heat of transition (ΔH) determined from the area of the endothermic peak of the sample was 8.52 cal. From the measured light transmittance and differential scanning calorific value, poly(N-
It can be seen that the aqueous solution of n-propylacrylamide has a transition temperature of 16-18°C.
第１図は、本発明のポリマーの水溶液の温度と光透過率
との関係を示すグラフで、第２図は温度と熱量との関係
を示すグラフである。FIG. 1 is a graph showing the relationship between temperature and light transmittance of an aqueous solution of the polymer of the present invention, and FIG. 2 is a graph showing the relationship between temperature and amount of heat.
Claims (1)
から実質的に成る転移温度１６〜１９℃をもつ親水性−
疎水性熱可逆型材料。1. A hydrophilic compound with a transition temperature of 16 to 19° C. consisting essentially of an aqueous solution of poly(N-n-propylacrylamide).
Hydrophobic thermoreversible material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5455082A JPS6048543B2 (en) | 1982-03-31 | 1982-03-31 | Hydrophilic-hydrophobic thermoreversible materials |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5455082A JPS6048543B2 (en) | 1982-03-31 | 1982-03-31 | Hydrophilic-hydrophobic thermoreversible materials |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58179256A JPS58179256A (en) | 1983-10-20 |
| JPS6048543B2 true JPS6048543B2 (en) | 1985-10-28 |
Family
ID=12973785
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5455082A Expired JPS6048543B2 (en) | 1982-03-31 | 1982-03-31 | Hydrophilic-hydrophobic thermoreversible materials |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6048543B2 (en) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60250018A (en) * | 1984-05-28 | 1985-12-10 | Mitsui Toatsu Chem Inc | Anti-fog method |
| JPS60250013A (en) * | 1984-05-28 | 1985-12-10 | Mitsui Toatsu Chem Inc | Humidity control method |
| JPS60168705A (en) * | 1984-02-14 | 1985-09-02 | Mitsui Toatsu Chem Inc | Temperature-sensitive polymer |
| JPS60168706A (en) * | 1984-02-14 | 1985-09-02 | Mitsui Toatsu Chem Inc | Temperature-sensitive copolymer |
| JPS60170608A (en) * | 1984-02-15 | 1985-09-04 | Mitsui Toatsu Chem Inc | Temperature-sensitive copolymer |
| JPS60170607A (en) * | 1984-02-15 | 1985-09-04 | Mitsui Toatsu Chem Inc | Temperature-sensitive polymer |
| JPS60170609A (en) * | 1984-02-16 | 1985-09-04 | Mitsui Toatsu Chem Inc | temperature sensitive copolymer |
| JPH089684B2 (en) * | 1984-05-07 | 1996-01-31 | 三井東圧化学株式会社 | Polymer complex |
| JPS60250016A (en) * | 1984-05-28 | 1985-12-10 | Mitsui Toatsu Chem Inc | Resin for retaining and releasing useful substance |
| JPS60250019A (en) * | 1984-05-28 | 1985-12-10 | Mitsui Toatsu Chem Inc | Resin for hydrogel |
| JPS60250015A (en) * | 1984-05-28 | 1985-12-10 | Mitsui Toatsu Chem Inc | Resin with permeation sorting ability |
| JPH06183B2 (en) * | 1984-05-28 | 1994-01-05 | 三井東圧化学株式会社 | Emulsification / demulsification method |
| ES2370758T3 (en) | 2007-11-09 | 2011-12-22 | Koninklijke Philips Electronics N.V. | LIGHT OUTPUT DEVICE |
-
1982
- 1982-03-31 JP JP5455082A patent/JPS6048543B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58179256A (en) | 1983-10-20 |
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