JPS6215565B2 - - Google Patents
Info
- Publication number
- JPS6215565B2 JPS6215565B2 JP18859784A JP18859784A JPS6215565B2 JP S6215565 B2 JPS6215565 B2 JP S6215565B2 JP 18859784 A JP18859784 A JP 18859784A JP 18859784 A JP18859784 A JP 18859784A JP S6215565 B2 JPS6215565 B2 JP S6215565B2
- Authority
- JP
- Japan
- Prior art keywords
- copolymer
- formula
- present
- methylolacrylamide
- repeating unit
- 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
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 11
- LCXIFAOALNZGDO-UHFFFAOYSA-N n-cyclopropylprop-2-enamide Chemical compound C=CC(=O)NC1CC1 LCXIFAOALNZGDO-UHFFFAOYSA-N 0.000 claims description 7
- 229920006322 acrylamide copolymer Polymers 0.000 claims description 6
- 238000010526 radical polymerization reaction Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 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
- 239000003463 adsorbent Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 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
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 238000002166 wet spinning Methods 0.000 description 1
Landscapes
- Separation Using Semi-Permeable Membranes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
産業上の利用分野
本発明は、熱可逆的特性を有する新規なアクリ
ルアミド系共重合体及びその製造方法、さらに詳
しくいえば水溶液状としたときに所定の温度以上
では白濁するが、その温度以下では透明化すると
いう、熱可逆特性を有し、温室、シヨーウインド
ウなどの遮光体、吸着剤、玩具、水呼吸体、被覆
材料、捺染剤、接着剤、分離膜、メカノケミカル
材料等として広く利用しうる新規なアクリルアミ
ド系共重合体及びその製造方法に関するものであ
る。
従来の技術
水溶液としたときに、所定の温度（転移温度又
は曇点）以上では析出して白濁状となりその温度
以下では溶解して透明化する水溶性高分子化合物
は、通常熱可逆高分子と称され、その可逆性を利
用して遮光体や吸着剤などへの応用がはかられて
いる。
これまで、アクリルアミド系の熱可逆高分子と
して、Ｎ−アルキル置換−アクリルアミド又はメ
タクリルアミドの重合体が知られている。
しかしながら、このアクリルアミド系熱可逆高
分子は、所要の形状に成形しても、低温下では水
に溶解し、その形状を保つことができないため、
おのずから用途が制限されるのを免れない。
アクリルアミド系重合体以外にも、多くの熱可
逆高分子が提案されているが、所定の形状を維持
したまま、高温で白濁し、低温で透明化するとい
うものは、放射線照射によるもの以外は知られて
いなかつた。
発明が解決しようとする問題点
本発明の目的は、成形後、容易に架橋させるこ
とができ、熱可逆物性を維持したまま低温におい
てもその形状を保ちうる成形体を与える新規なア
クリルアミド系共重合体を提供することである。
問題点を解決するための手段
本発明者らは、アクリルアミド系熱可逆高分子
について種々研究を重ねた結果、
Ｎ−シクロプロピルアクリルアミドとＮ−メチ
ロールアクリルアミドとを所定の割合で共重合さ
せて得られる共重合体は、熱可逆特性を有する上
に、容易に架橋化して水不溶性になることを見出
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−シクロプロピルアク
リルアミド単位とＮ−メチロールアクリルアミド
単位とから成り、Ｎ−メチロールアクリルアミド
単位の割合が全体の0.1〜30モル％で、かつ極限
粘度〔η〕0.01〜6.0に相当する分子量を有する
アクリルアミド系共重合体を提供するものであ
る。
このようなアクリルアミド系共重合体は、Ｎ−
シクロプロピルアクリルアミドとＮ−メチロール
アクリルアミドとを、モル比99.9：0.1ないし
70：30の割合で、溶液状態においてラジカル重合
させることによつて製造することができる。
この際の単量体として用いるＮ−シクロプロピ
ルアクリルアミドは本発明者が開発した新規化合
物であつて、例えばアクリル酸クロリドとシクロ
プロピルアミンとを脱塩酸剤例えばトリエチルア
ミンの存在下で反応させることによつて製造する
ことができる。また、このＮ−シクロプロピルア
クリルアミドと共重合させるＮ−メチロールアク
リルアミドは公知化合物であり、市販品として入
手することができる。
これらの単量体を共重合するには、単量体を均
一に混合しうる溶媒を用いて行うことが必要であ
る。このような溶媒の例としては、水、アルコー
ル、Ｎ・Ｎ−ジエチルアセトアミド、ジメチルス
ルホキシド、アセトン、ジオキサン、テトラヒド
ロフラン、ベンゼン、クロロホルム、四塩化炭素
などを挙げることができる。これらの溶媒は単独
で用いてもよいし、また２種以上組み合わせて用
いてもよい。
本発明方法においては、これらの溶媒中に、単
量体を１〜100重量％の濃度で溶解し、溶液状態
でラジカル重合させる。このラジカル重合は、通
常のラジカル重合開始剤例えばアゾビスイソブチ
ロニトリル、過酸化ベンゾイルなどの存在下で加
熱してもよいし、また放射線照射や光照射によつ
て行つてもよい。
本発明の共重合体では、式で表わされる繰り
返し単位の割合が全体の0.1〜30モル％であるこ
とが必要である。この割合が0.1モル％よりも少
ないと十分な架橋性が得られないし、また30モル
％よりも多くなると、水溶性高分子となるため、
所望の目的を達成することができなくなる。
本発明の共重合体は、メタノール溶液として、
30℃において0.01〜6.0、好ましくは0.1〜3.0の極
限粘度〔η〕を示す程度の分子量を有するので、
常法に従つて容易に成形することができる。
本発明の共重合体は、赤外吸収スペクトルにお
いて、メチロール基に基づく1035cm-1及びシクロ
プロピル基に基づく3080、3005、1450、1050及び
1025cm-1のピークを示すことにより、その同定を
行うことができる。
本発明の共重合体は、加熱すると、Ｎ−メチロ
ール基の間で脱水反応を起し、容易に架橋し、不
溶化する。したがつて、この共重合体を、慣用の
方法例えばキヤスト法、湿式紡糸法などによつて
成形したのち、乾式加熱することによつて、非水
溶性の成形体とすることができる。この際の架橋
化条件は、共重合体の組成、使用する反応温度や
反応時間に左右されるが、一般的に、式で表わ
される繰り返し単位が多いものは、反応温度が低
くなり、また反応時間が短かくなるし、式で表
わされる繰り返し単位が少ないものは、反応温度
が高くなり、反応時間が長くなる。通常は、反応
温度は100〜200℃、反応時間は１〜500分の範囲
内である。
本発明の共重合体の転移温度は、各単量体単位
のモル比に依存し、Ｎ−メチロールアクリルアミ
ドの割合の増加とともに高温側に移動する。した
がつて、このモル比を変えることによつて転移温
度を任意に調節することができる。
一方、この共重合体の熱応答感度は、Ｎ−メチ
ロールアクリルアミドの割合が増加するとともに
低下するが、この低下の割合は小さいので、全体
的に熱応答感度は良好である。
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。
実施例
Ｎ−シクロプロピルアクリルアミドとＮ−メチ
ロールアクリルアミドを種々の割合で混合し、ラ
ジカル重合させた。
重合開始剤としてアゾビスイソブチロニトリル
を用い、その濃度５mg／mlメタノール溶液20mlを
所定の組成及び濃度に調整したモノマーのメタノ
ール溶液中に投入し、反応温度50℃で40時間反応
させた。反応後メタノールを除去してアセトン溶
液とし、ジエチルエーテルに沈殿させポリマーを
回収した。共重合体中のＮ−メチロールアクリル
アミド分率は、重合率100％と仮定して算出し
た。
各実験におけるモノマー仕込量、共重合体中の
Ｎ−メチロールアクリルアミド分率、転移温度を
次表に示す。この転移温度は、１％濃度の共重合
体水溶液を調製し、これを温度調節付分光光度計
にセツトし、昇温速度１℃／分で昇温させながら
波長500nｍにおける光透過率変化をプロツトし
てグラフを作成し、光透過率が初期透過率の1/2
となる点から求めた。この際の光透過率変化のグ
ラフを図に示す。
Industrial Application Field The present invention relates to a novel acrylamide copolymer having thermoreversible properties and a method for producing the same.More specifically, when it is made into an aqueous solution, it becomes cloudy above a certain temperature, but below that temperature, it becomes cloudy. It has thermoreversible properties of becoming transparent and is widely used as light shielding materials for greenhouses, show windows, etc., adsorbents, toys, water breathing bodies, coating materials, printing agents, adhesives, separation membranes, mechanochemical materials, etc. The present invention relates to a novel acrylamide-based copolymer and a method for producing the same. Prior Art Water-soluble polymer compounds that, when made into an aqueous solution, precipitate and become cloudy at temperatures above a certain temperature (transition temperature or cloud point) and dissolve and become transparent below that temperature are usually called thermoreversible polymers. Its reversibility is being used to find applications in light shielding materials, adsorbents, etc. Until now, N-alkyl-substituted acrylamide or methacrylamide polymers have been known as acrylamide-based thermoreversible polymers. However, even if this acrylamide-based thermoreversible polymer is molded into the desired shape, it dissolves in water at low temperatures and cannot maintain its shape.
Naturally, it is inevitable that its uses will be limited. In addition to acrylamide-based polymers, many thermoreversible polymers have been proposed, but there are no polymers that become cloudy at high temperatures and transparent at low temperatures while maintaining a predetermined shape, other than those caused by radiation irradiation. It wasn't. Problems to be Solved by the Invention The object of the present invention is to provide a novel acrylamide copolymer that can be easily crosslinked after molding and that can maintain its shape even at low temperatures while maintaining thermoreversible physical properties. It is to provide a combination. Means for Solving the Problems As a result of various studies on acrylamide-based thermoreversible polymers, the present inventors have found that they can be obtained by copolymerizing N-cyclopropylacrylamide and N-methylolacrylamide in a predetermined ratio. It was discovered that the copolymer has thermoreversible properties and is easily crosslinked to become water-insoluble, and based on this knowledge, the present invention was accomplished. That is, the present invention is composed of N-cyclopropylacrylamide units and N-methylolacrylamide units, and the proportion of N-methylolacrylamide units is 0.1 to 30 mol% of the total, and corresponds to an intrinsic viscosity [η] of 0.01 to 6.0. The purpose of the present invention is to provide an acrylamide copolymer having a molecular weight of Such an acrylamide copolymer has N-
Cyclopropylacrylamide and N-methylolacrylamide in a molar ratio of 99.9:0.1 to
It can be produced by radical polymerization in solution at a ratio of 70:30. N-cyclopropylacrylamide used as a monomer in this case is a new compound developed by the present inventor, and is produced by, for example, reacting acrylic acid chloride and cyclopropylamine in the presence of a dehydrochlorination agent such as triethylamine. It can be manufactured by Further, N-methylolacrylamide to be copolymerized with this N-cyclopropylacrylamide is a known compound and can be obtained as a commercially available product. In order to copolymerize these monomers, it is necessary to use a solvent that can uniformly mix the monomers. Examples of such solvents include water, alcohol, N·N-diethylacetamide, dimethyl sulfoxide, acetone, dioxane, tetrahydrofuran, benzene, chloroform, carbon tetrachloride, and the like. These solvents may be used alone or in combination of two or more. In the method of the present invention, monomers are dissolved in these solvents at a concentration of 1 to 100% by weight, and radical polymerization is carried out in a solution state. This radical polymerization may be carried out by heating in the presence of a conventional radical polymerization initiator such as azobisisobutyronitrile or benzoyl peroxide, or by irradiation with radiation or light. In the copolymer of the present invention, the proportion of the repeating unit represented by the formula must be 0.1 to 30 mol% of the total. If this proportion is less than 0.1 mol%, sufficient crosslinking properties cannot be obtained, and if it exceeds 30 mol%, the polymer becomes water-soluble.
It becomes impossible to achieve the desired objective. The copolymer of the present invention can be prepared as a methanol solution.
Since it has a molecular weight that exhibits an intrinsic viscosity [η] of 0.01 to 6.0, preferably 0.1 to 3.0 at 30°C,
It can be easily molded according to conventional methods. The copolymer of the present invention has an infrared absorption spectrum of 1035 cm -1 based on the methylol group and 3080, 3005, 1450, 1050 cm -1 based on the cyclopropyl group, and
It can be identified by showing the peak at 1025 cm -1 . When the copolymer of the present invention is heated, a dehydration reaction occurs between the N-methylol groups, and the copolymer is easily crosslinked and becomes insolubilized. Therefore, a water-insoluble molded article can be obtained by molding this copolymer by a conventional method such as a casting method or a wet spinning method, and then dry heating it. The crosslinking conditions at this time depend on the composition of the copolymer, the reaction temperature and reaction time used, but in general, the more repeating units represented by the formula, the lower the reaction temperature and the reaction time. The reaction time will be shorter, and if there are fewer repeating units represented by the formula, the reaction temperature will be higher and the reaction time will be longer. Usually, the reaction temperature is in the range of 100 to 200°C and the reaction time is in the range of 1 to 500 minutes. The transition temperature of the copolymer of the present invention depends on the molar ratio of each monomer unit, and shifts toward higher temperatures as the proportion of N-methylolacrylamide increases. Therefore, by changing this molar ratio, the transition temperature can be adjusted as desired. On the other hand, the thermal response sensitivity of this copolymer decreases as the proportion of N-methylolacrylamide increases, but the rate of this decrease is small, so the thermal response sensitivity is good overall. Examples Next, the present invention will be explained in more detail with reference to Examples. Examples N-cyclopropylacrylamide and N-methylolacrylamide were mixed in various ratios and subjected to radical polymerization. Using azobisisobutyronitrile as a polymerization initiator, 20 ml of a methanol solution with a concentration of 5 mg/ml was poured into a methanol solution of monomers adjusted to a predetermined composition and concentration, and the reaction was carried out at a reaction temperature of 50° C. for 40 hours. After the reaction, methanol was removed to obtain an acetone solution, which was precipitated in diethyl ether to recover the polymer. The N-methylolacrylamide fraction in the copolymer was calculated assuming a polymerization rate of 100%. The amount of monomer charged, the N-methylolacrylamide fraction in the copolymer, and the transition temperature in each experiment are shown in the following table. This transition temperature was determined by preparing a 1% copolymer aqueous solution, setting it in a temperature-controlled spectrophotometer, and plotting the change in light transmittance at a wavelength of 500 nm while increasing the temperature at a rate of 1°C/min. Create a graph and set the light transmittance to 1/2 of the initial transmittance.
It was found from the point that A graph of the change in light transmittance at this time is shown in the figure.
【表】
試料No.２ないし、No.４はこれをフイルム状に成
形し、150℃で１時間乾式加熱したところ、加熱
前の形状を維持したまま架橋し、不溶化したが、
試料No.１は全く架橋しなかつた。
また、試料No.５及び６は水溶性となり熱可逆性
を示さなかつた。
発明の効果
本発明の共重合体は、熱可逆特性に加え、架橋
性能を有しているため、これを成形後加熱処理す
ることにより、容易に架橋させて不溶化すること
ができるという利点を有している。
したがつて、この共重合体はメカノケミカル材
料、遮光材、吸着剤、玩具素材、分離膜などとし
て広く利用することができる。[Table] When samples No. 2 to No. 4 were formed into a film and dry heated at 150°C for 1 hour, they were crosslinked and insolubilized while maintaining the shape before heating.
Sample No. 1 was not crosslinked at all. Moreover, Samples Nos. 5 and 6 were water-soluble and did not exhibit thermoreversibility. Effects of the Invention The copolymer of the present invention has crosslinking performance in addition to thermoreversible properties, so it has the advantage that it can be easily crosslinked and made insolubilized by heat treatment after molding. are doing. Therefore, this copolymer can be widely used as mechanochemical materials, light shielding materials, adsorbents, toy materials, separation membranes, etc.
図は、実施例で得た共重合体水溶液の光透過率
と温度の関係を示すグラフである。
The figure is a graph showing the relationship between light transmittance and temperature of copolymer aqueous solutions obtained in Examples.
Claims (1)
で表わされる単位の割合が全体の0.1〜30モル％
で、かつ極限粘度〔η〕0.01〜6.0に相当する分
子量を有するアクリルアミド系共重合体。 ２ Ｎ−シクロプロピルアクリルアミドとＮ−メ
チロールアクリルアミドとを、モル比99.9：0.1
ないし70：30の割合で、溶液状態においてラジカ
ル重合させることを特徴とする 式（） で表わされる繰り返し単位と 式（） で表わされる繰り返し単位とから成り、式（）
で表わされる単位の割合が全体の0.1〜30モル％
で、かつ極限粘度〔η〕0.01〜6.0に相当する分
子量を有するアクリルアミド系共重合体の製造方
法。[Claims] 1 Formula () The repeating unit represented by and the formula () It consists of a repeating unit represented by the formula ()
The proportion of units represented by is 0.1 to 30 mol% of the total
An acrylamide copolymer having a molecular weight corresponding to an intrinsic viscosity [η] of 0.01 to 6.0. 2 N-cyclopropylacrylamide and N-methylolacrylamide at a molar ratio of 99.9:0.1
Formula () characterized by radical polymerization in a solution state at a ratio of 70:30 The repeating unit represented by and the formula () It consists of a repeating unit represented by the formula ()
The proportion of units represented by is 0.1 to 30 mol% of the total
A method for producing an acrylamide copolymer having a molecular weight corresponding to an intrinsic viscosity [η] of 0.01 to 6.0.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18859784A JPS6166707A (en) | 1984-09-08 | 1984-09-08 | Production of crosslinkable, thermally reversible high polymer compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18859784A JPS6166707A (en) | 1984-09-08 | 1984-09-08 | Production of crosslinkable, thermally reversible high polymer compound |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13223286A Division JPS61287931A (en) | 1986-06-07 | 1986-06-07 | Production of thermoreversible high-molecular crosslinked molding |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6166707A JPS6166707A (en) | 1986-04-05 |
| JPS6215565B2 true JPS6215565B2 (en) | 1987-04-08 |
Family
ID=16226438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18859784A Granted JPS6166707A (en) | 1984-09-08 | 1984-09-08 | Production of crosslinkable, thermally reversible high polymer compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6166707A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2525407B2 (en) * | 1987-05-08 | 1996-08-21 | 三井東圧化学株式会社 | Separation membrane |
| US5104954A (en) * | 1987-10-05 | 1992-04-14 | Ciba-Geigy Corporation | Thermostropic biphilic hydrogels and hydroplastics |
| AU2003233400A1 (en) | 2002-03-15 | 2003-09-29 | The Penn State Research Foundation | Method for control of temperature-sensitivity of polymers in solution |
-
1984
- 1984-09-08 JP JP18859784A patent/JPS6166707A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6166707A (en) | 1986-04-05 |
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