JPH0623375B2 - Temperature-sensitive composition - Google Patents
Temperature-sensitive compositionInfo
- Publication number
- JPH0623375B2 JPH0623375B2 JP59235082A JP23508284A JPH0623375B2 JP H0623375 B2 JPH0623375 B2 JP H0623375B2 JP 59235082 A JP59235082 A JP 59235082A JP 23508284 A JP23508284 A JP 23508284A JP H0623375 B2 JPH0623375 B2 JP H0623375B2
- Authority
- JP
- Japan
- Prior art keywords
- temperature
- sensitive composition
- polymer
- water
- monomer
- 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 - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims description 19
- 239000000178 monomer Substances 0.000 claims description 20
- 229920000642 polymer Polymers 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 15
- 230000007704 transition Effects 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 8
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 5
- 125000006353 oxyethylene group Chemical group 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- -1 polyoxyethylene groups Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229920003169 water-soluble polymer Polymers 0.000 description 2
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000012690 ionic polymerization Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は温度変化に伴って、透明状態から不透明状態に
可逆的に相変化する感温性組成物に関する。本発明の組
成物は、ある温度を境に可逆的に相転移現象を示して親
水性疎水性を示すものであり、これらは感温性素材と
して、センサーや遮光体あるいは熱可逆型吸着剤など多
分野のへの応用が可能である。The present invention relates to a temperature-sensitive composition that reversibly changes its phase from a transparent state to an opaque state with a change in temperature. The composition of the present invention reversibly exhibits a phase transition phenomenon at a certain temperature and exhibits hydrophilicity and hydrophobicity, and these are temperature-sensitive materials such as a sensor, a light shield or a thermoreversible adsorbent. It can be applied to various fields.
従来、熱可逆的溶解挙動を示す水溶性分子としては、ポ
リビニルアルコールの部分ケン化物、ポリエチレンオキ
シドが知られている。これらの水溶性高分子の相転移温
度（くもり点）はぞれぞれ９０〜１００℃，９５〜１０
０℃という高温領域にある。Conventionally, as a water-soluble molecule exhibiting thermoreversible dissolution behavior, a partially saponified product of polyvinyl alcohol and polyethylene oxide are known. The phase transition temperatures (cloudy points) of these water-soluble polymers are 90 to 100 ° C. and 95 to 10 ° C., respectively.
It is in a high temperature region of 0 ° C.
前述水溶性高分子は相転移温度が９０℃以上と高く、ま
た温度範囲もせまいなどの欠点を有しており、比較的低
温での作動が要求されるセンサー、遮光体あるいは熱可
逆型吸着剤などへの応用が困難であるという問題点があ
った。The above-mentioned water-soluble polymer has drawbacks such as a high phase transition temperature of 90 ° C. or higher and a narrow temperature range. Therefore, a sensor, a light shield or a thermoreversible adsorbent which is required to operate at a relatively low temperature. However, there is a problem that it is difficult to apply to.
本発明者は、前記のような欠点のない感温性組成物を得
るために研究を重ねた結果、オキシエチレン基を側鎖に
有する重合体が、オキシエチレン単位の含有量や側鎖の
オキシエチレン鎖長などを制御することにより、自由に
相転移温度を変化しうる事を見いだして本発明に至っ
た。The present inventor has conducted extensive research in order to obtain a temperature-sensitive composition without the above-mentioned drawbacks, and as a result, a polymer having an oxyethylene group in the side chain has a oxyethylene unit content or an oxyethylene unit in the side chain. The present invention has been completed by finding that the phase transition temperature can be freely changed by controlling the ethylene chain length and the like.
すなわち、本発明は、下記一般式(I)で示される単量体
の１種または２種以上の単量体を重合または一般式(I)
で示される単量体と他のエチレン性不飽和単量体とを共
重合して得られる重合体と水とを含む感温性組成物を提
供するものである。That is, the present invention is characterized by polymerizing one or more monomers of the following general formula (I) or the general formula (I)
The present invention provides a temperature-sensitive composition containing water and a polymer obtained by copolymerizing the monomer represented by the above with another ethylenically unsaturated monomer.
（但し式中、Ｒ１は水素またはメチル基を表わし、Ｒ２
は炭素数１から４のアルキル基またはフェニル基を表わ
す。ｎは２〜５０の整数を表わす。） 本発明に使用する一般式(I)で示される単量体の具体例
としては、たとえばメトキシ（ポリ）エチレングリコー
ルモノアクリレート，メトキシ（ポリ）エチレングリコ
ールモノメタクリレート，エトキシ（ポリ）エチレング
リコールモノアクリレート，エトキシ（ポリ）エチレン
グリコールモノメタクリレート，ｎ−プロピル（ポリ）
エチレングリコールモノアクリレート，ｎ−プロピル
（ホリ）エチレングリコールモノメタクリレート，イソ
プロピル（ポリ）エチレングリコールモノアクリレー
ト，イソプロピル（ポリ）エチレングリコールモノメタ
クリレート，ｎ−ブチル（ポリ）エチレングリコールモ
ノアクリレート，ｎ−ブチル（ポリ）エチレングリコー
ルモノメクリレート，イソブチル（ポリ）エチレングリ
コールモノアクリレート、イソブチル（ポリ）エチレン
グリコールモノメタクリレート，ｔ−ブチル（ポリ）エ
チレングリコールモノアクリレート，ｔ−ブチル（ポ
リ）エチレングリコールモノメタクリレート，フェノキ
シ（ポリ）エチレングリコールモノアクリレート，フェ
ノキシ（ポリ）エチレングリコールモノメタクリレート
などがある。 (In the formula, R 1 represents hydrogen or a methyl group, and R 2
Represents an alkyl group having 1 to 4 carbon atoms or a phenyl group. n represents an integer of 2 to 50. ) Specific examples of the monomer represented by the general formula (I) used in the present invention include, for example, methoxy (poly) ethylene glycol monoacrylate, methoxy (poly) ethylene glycol monomethacrylate, ethoxy (poly) ethylene glycol monoacrylate. , Ethoxy (poly) ethylene glycol monomethacrylate, n-propyl (poly)
Ethylene glycol monoacrylate, n-propyl (holi) ethylene glycol monomethacrylate, isopropyl (poly) ethylene glycol monoacrylate, isopropyl (poly) ethylene glycol monomethacrylate, n-butyl (poly) ethylene glycol monoacrylate, n-butyl (poly ) Ethylene glycol monomethacrylate, isobutyl (poly) ethylene glycol monoacrylate, isobutyl (poly) ethylene glycol monomethacrylate, t-butyl (poly) ethylene glycol monoacrylate, t-butyl (poly) ethylene glycol monomethacrylate, phenoxy (poly) ) Ethylene glycol monoacrylate, phenoxy (poly) ethylene glycol monomethacrylate, etc.
上記単量体中のオキシエチレン単位の繰り返し数ｎは２
〜５０であり、好ましくは〜３０である。The repeating number n of oxyethylene units in the above monomer is 2
It is -50, preferably -30.
共重合可能な他のエチレン性不飽和単量体の例として
は、たとえばアクリル酸アルキルエステル，メタクリル
酸アルキルエステル，アクリロニトリル，酢酸ビニル，
スチレンなどがある。Examples of the other copolymerizable ethylenically unsaturated monomer include, for example, acrylic acid alkyl ester, methacrylic acid alkyl ester, acrylonitrile, vinyl acetate,
Styrene etc.
重合方法としては、ラジカル重合触媒の存在下で溶液、
乳化、懸濁、塊状などの重合方法のほかイオン重合、光
重合など公知の方法が利用できる。As the polymerization method, a solution in the presence of a radical polymerization catalyst,
In addition to polymerization methods such as emulsification, suspension, and bulk, known methods such as ionic polymerization and photopolymerization can be used.
本発明に用いる重合体の分子量について時に制限はない
が、５０００〜５０万程度のものが使用できる。The molecular weight of the polymer used in the present invention is not particularly limited, but those having a molecular weight of about 5,000 to 500,000 can be used.
本発明に用いる重合体が効果的に相転移現象を示すため
には、この重合体が一般式(I)で示される単量体を１０
〜１００重量％含む単量体を重合または共重合して得た
ものであることが好ましく、さらに好ましくは３０〜１
００重量％のものである。In order for the polymer used in the present invention to effectively exhibit the phase transition phenomenon, the polymer may be prepared by adding the monomer represented by the general formula (I) to 10
It is preferably obtained by polymerizing or copolymerizing a monomer containing 100 to 100% by weight, and more preferably 30 to 1
It is of 100% by weight.
本発明の感温性組成物が所定の相転移現象を示すために
は、前記重合体と水とが共存する必要があり、その含水
率は０．５〜９９．５重量％が好ましく、特に好ましく
は１〜９９重量％である。In order for the temperature-sensitive composition of the present invention to exhibit a predetermined phase transition phenomenon, the polymer and water must coexist, and the water content is preferably 0.5 to 99.5% by weight, and particularly, It is preferably 1 to 99% by weight.
本発明の感温性組成物は、重合体中に含まれるオキシエ
チレン単位の含有量によって相転移温度を変化させるこ
とができる。すなわち相転移温度は、使用する一般式
(I)で示される単量体と他のエチレン性不飽和単量体の
種類およびその配合量、単量体の配列のしかたによって
任意に選択することができる。また、感温性組成物の物
性も、単量体の種類や配合組成および水の含有量によ
り、液状から可とう性のある固体まで任意のもを選択す
ることができる。The temperature-sensitive composition of the present invention can change the phase transition temperature depending on the content of oxyethylene units contained in the polymer. That is, the phase transition temperature is the general formula used
It can be arbitrarily selected depending on the types of the monomer represented by (I) and other ethylenically unsaturated monomers, their blending amounts, and the arrangement of the monomers. The physical properties of the temperature-sensitive composition can be selected from liquid to flexible solid depending on the type of monomer, the composition of the composition and the content of water.
本発明の感温性組成物に、他に必要ならば、無機塩，色
素，保存剤，溶媒などを適宜添加して使用することがで
きる。If necessary, an inorganic salt, a dye, a preservative, a solvent and the like can be appropriately added to the temperature-sensitive composition of the present invention before use.
本発明の感温性組成物は、前記一般式(I)で示される単
量体を重合または共重合して得た、側鎖に親水性のポリ
オキシエチレン基を多数有する特殊な重合体を用いてお
り、相転移温度や物性を自由に選ぶことができるので、
広い温度範囲、特に９０℃以下の温度において作動する
感温性組成物として種々の形態で利用することができ
る。The temperature-sensitive composition of the present invention is obtained by polymerizing or copolymerizing the monomer represented by the general formula (I), a special polymer having a large number of hydrophilic polyoxyethylene groups in the side chain. Since it is used and the phase transition temperature and physical properties can be freely selected,
It can be used in various forms as a temperature-sensitive composition that operates in a wide temperature range, particularly at a temperature of 90 ° C. or lower.
次に製造例、実施例、比較例によって具体的に本発明を
説明する。例中の部は重量部、分子量はＧＰＣ法による
重合平均分子量を表わす。これらの製造例、実施例は説
明の目的で述べるものであって本発明になんらの制限を
加えるものではない。Next, the present invention will be specifically described with reference to production examples, examples and comparative examples. Parts in the examples are parts by weight, and molecular weights are polymerization average molecular weights determined by the GPC method. These production examples and examples are described for the purpose of explanation and do not impose any limitation on the present invention.
製造例 かく拌機付きフラスコに、トルエンを４０部仕込み、窒
素を吹き込みつつ１００℃に昇温し、かく拌しながら、
トルエン２０部、表−１に示した配合比の単量体を４０
部、ｔ−ブチルペルオキシ−２−エチルヘキサノエート
０．８部の混合溶液を２時間で滴下し、滴下終了後１１
０℃に昇温して８時間反応させた。反応溶液を冷却後、
ｎ−ヘキサン１０００部に注いで重合体ａ〜ｉを得た。
各々の分子量と性状を表−１に示した。Production Example A flask equipped with a stirrer was charged with 40 parts of toluene, heated to 100 ° C. while blowing nitrogen, and stirred,
20 parts of toluene, 40 parts of the monomer of the compounding ratio shown in Table-1
Part, and a mixed solution of 0.8 part of t-butylperoxy-2-ethylhexanoate were added dropwise over 2 hours, and after the addition was completed, 11
The temperature was raised to 0 ° C. and the reaction was carried out for 8 hours. After cooling the reaction solution,
Polymers a to i were obtained by pouring into 1000 parts of n-hexane.
The molecular weight and properties of each are shown in Table-1.
実施例１〜３ 重合体ａ，ｂ，ｃを１ｇづつ試験管に取り、イオン交換
水１００ｇを加えて、１０℃の恒温槽中で溶解した。溶
解後所徐々に昇温して溶液が白濁したときの恒温槽の温
度から相転移温度をもとめた。白濁物を冷却すると再度
透明溶液にもどった。結果を表−２に示した。Examples 1 to 3 Polymers a, b, and 1 g were taken in test tubes one by one, 100 g of ion-exchanged water was added, and the polymers were dissolved in a constant temperature bath at 10 ° C. After the dissolution, the temperature was gradually raised and the phase transition temperature was determined from the temperature in the constant temperature bath when the solution became cloudy. When the white turbidity was cooled, it returned to the clear solution again. The results are shown in Table-2.
比較例 重合体ｄ〜ｉをトルエンに溶解し、ガラス板上にキャス
トした。室温で２４時間放置後、５０℃で２４時間真空
乾燥を行い、厚さ０．５mmの透明なシートを得た。これ
をポリエチレンシートでサンドイッチ状にはさみ加熱シ
ールにより密封した。それぞれのシートを恒温槽に没入
し５℃から徐々に昇温を行ったが、１００℃まで相転移
現象は認められなかった。Comparative Example Polymers d to i were dissolved in toluene and cast on a glass plate. After leaving at room temperature for 24 hours, vacuum drying was performed at 50 ° C. for 24 hours to obtain a transparent sheet having a thickness of 0.5 mm. This was sandwiched between polyethylene sheets and sealed with a heat seal. Each sheet was immersed in a thermostat and gradually heated from 5 ° C, but no phase transition phenomenon was observed up to 100 ° C.
実施例４〜９ 比較例に示した方法により、重合体ｄ〜ｉのシートを得
た。更にこれらのシートを室温でイオン交換水に１昼夜
浸漬して含水シーを作った。Examples 4 to 9 Sheets of polymers d to i were obtained by the method shown in the comparative example. Further, these sheets were immersed in ion-exchanged water at room temperature for one day to prepare a water-containing sheet.
これらのシートを０℃に冷却すると透明で可とう性のあ
るシートが得られた。なお、これらの含水シートの含水
率は表−２に示した。When these sheets were cooled to 0 ° C., transparent and flexible sheets were obtained. The water contents of these water-containing sheets are shown in Table 2.
これらの含水シートを試験管にとり、イオン交換水を加
えて恒温槽に没入し、徐々に昇温しながら、シートが白
濁したときの恒温槽の温度から相転移温度を求めた。結
果を表−２に示した。なお、白濁した含水シートは冷却
すると透明にもどった。These water-containing sheets were placed in a test tube, ion-exchanged water was added, and the sheets were immersed in a thermostatic bath, and the phase transition temperature was determined from the temperature of the thermostatic bath when the sheet became cloudy while gradually raising the temperature. The results are shown in Table-2. The cloudy water-containing sheet became transparent when cooled.
実施例および比較例から明らかなように、本発明の感温
性組成物は、水が存在する場合に相転移現象を示すこと
がわかる。また、その相転移温度は、単量体の種類およ
び組成を変えて得られる重合体の種類および水の量によ
り３〜９０℃と大きく変化することがわかる。さらに、
感温性組成物の物性も溶液状から可とう性のある固体ま
で任意のものが選択できる。 As is clear from the examples and comparative examples, it can be seen that the temperature-sensitive composition of the present invention exhibits a phase transition phenomenon in the presence of water. Further, it can be seen that the phase transition temperature greatly changes from 3 to 90 ° C. depending on the kind of the polymer obtained by changing the kind and composition of the monomer and the amount of water. further,
The physical properties of the temperature-sensitive composition can be arbitrarily selected from a solution state to a flexible solid state.
Claims (3)
または２種以上を重合、または一般式（Ｉ）で示される
単量体と他のエチレン性不飽和単量体とを共重合して得
られる重合体と水とを含む感温性組成物。 （但し式中、Ｒ1は水素またはメチル基を表わし、Ｒ２
は炭素数１から４のアルキル基またはフェニル基を表わ
す。ｎは２〜５０の整数を表わす。）1. A polymer of one or more monomers represented by the following general formula (I), or a monomer represented by the general formula (I) and another ethylenically unsaturated monomer. A temperature-sensitive composition containing a polymer obtained by copolymerizing the above and water. (In the formula, R 1 represents hydrogen or a methyl group, and R 2
Represents an alkyl group having 1 to 4 carbon atoms or a phenyl group. n represents an integer of 2 to 50. )
許請求の範囲第１項記載の感温性組成物。2. The temperature-sensitive composition according to claim 1, which has a water content of 0.5 to 99.5% by weight.
を１０〜１００重量％含む単量体を重合または共重合し
て得たものである特許請求の範囲第１項または第２項記
載の感温性組成物。3. The polymer according to claim 1, wherein the polymer is obtained by polymerizing or copolymerizing a monomer containing 10 to 100% by weight of the monomer represented by the general formula (I). The temperature-sensitive composition according to item 2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59235082A JPH0623375B2 (en) | 1984-11-09 | 1984-11-09 | Temperature-sensitive composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59235082A JPH0623375B2 (en) | 1984-11-09 | 1984-11-09 | Temperature-sensitive composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61113639A JPS61113639A (en) | 1986-05-31 |
| JPH0623375B2 true JPH0623375B2 (en) | 1994-03-30 |
Family
ID=16980794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59235082A Expired - Lifetime JPH0623375B2 (en) | 1984-11-09 | 1984-11-09 | Temperature-sensitive composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0623375B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4746984B2 (en) * | 2003-03-28 | 2011-08-10 | 独立行政法人科学技術振興機構 | Polymer with both biocompatibility and temperature response |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS588776A (en) * | 1981-07-09 | 1983-01-18 | Agency Of Ind Science & Technol | Temperature-sensitive material |
| JPS6015850B2 (en) * | 1982-07-21 | 1985-04-22 | 高木産業株式会社 | Water heater antifreeze device |
-
1984
- 1984-11-09 JP JP59235082A patent/JPH0623375B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61113639A (en) | 1986-05-31 |
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