JP2005288317A - Nanocapsule manufacturing method - Google Patents
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- JP2005288317A JP2005288317A JP2004107097A JP2004107097A JP2005288317A JP 2005288317 A JP2005288317 A JP 2005288317A JP 2004107097 A JP2004107097 A JP 2004107097A JP 2004107097 A JP2004107097 A JP 2004107097A JP 2005288317 A JP2005288317 A JP 2005288317A
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- 239000002088 nanocapsule Substances 0.000 title claims abstract description 51
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 22
- 239000002775 capsule Substances 0.000 claims abstract description 37
- 239000012071 phase Substances 0.000 claims abstract description 21
- 239000007791 liquid phase Substances 0.000 claims abstract description 12
- 238000002844 melting Methods 0.000 claims abstract description 11
- 230000008018 melting Effects 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 239000000178 monomer Substances 0.000 claims abstract description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 9
- 239000006185 dispersion Substances 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 7
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 239000003505 polymerization initiator Substances 0.000 abstract description 8
- 239000004094 surface-active agent Substances 0.000 abstract description 8
- 239000000126 substance Substances 0.000 abstract description 6
- 239000012752 auxiliary agent Substances 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 3
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 239000013076 target substance Substances 0.000 abstract 1
- 239000001993 wax Substances 0.000 description 24
- 239000000243 solution Substances 0.000 description 14
- 238000010526 radical polymerization reaction Methods 0.000 description 11
- 239000004793 Polystyrene Substances 0.000 description 9
- 229920002223 polystyrene Polymers 0.000 description 9
- 238000005259 measurement Methods 0.000 description 8
- 239000012188 paraffin wax Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 5
- 210000003000 inclusion body Anatomy 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 238000010586 diagram Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000012790 confirmation Methods 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 239000002105 nanoparticle Substances 0.000 description 2
- 238000012695 Interfacial polymerization Methods 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000002052 molecular layer Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
Landscapes
- Manufacturing Of Micro-Capsules (AREA)
- Polymerisation Methods In General (AREA)
Abstract
Description
本発明は、ナノカプセル製造方法に係り、特に蝋相を被封入体としたナノカプセルを化学的方法により製造するナノカプセル製造方法に関する。 The present invention relates to a nanocapsule production method, and more particularly to a nanocapsule production method for producing a nanocapsule having a wax phase as an encapsulated body by a chemical method.
近年、種々の産業分野においてナノカプセルの製造が盛んに行われている。 In recent years, nanocapsules have been actively produced in various industrial fields.
例えば、ワックス等の蝋相からなる被封入体をポリスチレン等の高分子物質によって被覆したナノカプセルを製造する場合には、化学的方法の界面重合法によって製造されるものであるが、従来においては、重合開始剤や界面活性剤の添加が必要とされていた。また、化学的方法によって製造されたナノカプセルの均質化を図るために超音波を用いて振動を付与することが行われていた（例えば、特許文献１参照）。 For example, in the case of producing a nanocapsule in which an encapsulated body composed of a wax phase such as wax is coated with a polymer substance such as polystyrene, it is produced by an interfacial polymerization method of a chemical method. The addition of a polymerization initiator or a surfactant has been required. Moreover, in order to homogenize the nanocapsules manufactured by a chemical method, vibration has been applied using ultrasonic waves (see, for example, Patent Document 1).
しかしながら、従来の化学的方法においては被封入体となる蝋相とカプセル媒体との組み合わせに適正に対応した重合開始剤や界面活性剤を選択する必要があり、また得られるナノカプセルの性質にこれらの重合開始剤や界面活性剤も影響することとなり、真の目的とするナノカプセルを製造することができないという問題点があった。また、従来においては、ナノカプセルを短時間に大量生産することもできなかった。 However, in the conventional chemical method, it is necessary to select a polymerization initiator and a surfactant that appropriately correspond to the combination of the wax phase to be encapsulated and the capsule medium. In other words, the polymerization initiators and the surfactants are also affected, and the true target nanocapsules cannot be produced. In the past, nanocapsules could not be mass-produced in a short time.
本発明はこれらの点に鑑みてなされたものであり、重合開始剤や界面活性剤等の助剤を用いることなく目的とする被封入体となる蝋相を目的とするカプセル媒体によって被覆したナノカプセルを良好にかつ確実に製造することができ、更に生産効率もよく短時間に大量生産可能なナノカプセル製造方法を提供することを目的とするものである。 The present invention has been made in view of these points, and a nano-layer coated with a target capsule medium on a wax phase to be a target inclusion body without using an auxiliary agent such as a polymerization initiator or a surfactant. It is an object of the present invention to provide a nanocapsule production method capable of producing capsules satisfactorily and surely and having high production efficiency and capable of mass production in a short time.
本発明者等は鋭意研究し、従来既に製造されたナノカプセルの均質化の手段として用いられている超音波を利用して、最初に比較的低い周波数の超音波を照射することにより分散用の液相中において被封入体となる蝋相をカプセル媒体のモノマーによって被覆した微小滴に分散させ、その後比較的周波数の高い超音波を照射することによってモノマー状のカプセル媒体をラジカル重合させることによってカプセル媒体を重合させることができることを発見して本発明を完成させた。 The present inventors have intensively studied and used ultrasonic waves that have been conventionally used as a means for homogenizing nanocapsules that have already been produced. Capsules are obtained by dispersing the wax phase to be encapsulated in the liquid phase into fine droplets coated with the monomer of the capsule medium, and then subjecting the monomeric capsule medium to radical polymerization by irradiating ultrasonic waves with a relatively high frequency. The present invention has been completed by discovering that the medium can be polymerized.
従って、本発明のナノカプセルの製造方法は、分散用の液相に対して、重合体からなるナノカプセルを形成するカプセル媒体のモノマーと当該ナノカプセル内に封入される被封入体となる融点以上に加熱された状態の蝋相との混合物を添加し、その後全体に超音波を照射して前記液相内に前記カプセル媒体によって前記被封入体を被覆した微小滴を分散させ、その後更に超音波を照射することにより前記微小滴のカプセル媒体を重合させてナノカプセルとさせることを特徴とする。これにより、本発明によれば、重合開始剤や界面活性剤等の助剤を用いることなく目的とする被封入体となる蝋相を目的とするカプセル媒体によって被覆したナノカプセルを良好にかつ確実に製造することができ、更に生産効率もよく短時間に大量生産可能なものとなる。 Therefore, the method for producing nanocapsules of the present invention is such that, for the liquid phase for dispersion, the monomer of the capsule medium forming the nanocapsules made of a polymer and the melting point of the encapsulated material enclosed in the nanocapsules Then, a mixture with the heated wax phase is added, and then the whole is irradiated with ultrasonic waves to disperse the microdroplets coated with the encapsulated material by the capsule medium in the liquid phase, and then further ultrasonic , The microdroplet capsule medium is polymerized to form nanocapsules. Thus, according to the present invention, the nanocapsules coated with the target capsule medium on the wax phase that becomes the target inclusion body without using an auxiliary agent such as a polymerization initiator or a surfactant can be obtained reliably and reliably. In addition, the production efficiency is good and the mass production is possible in a short time.
また、前記カプセル媒体を重合させる時の超音波の周波数をその前の分散時の周波数より高くするとよい。これによりカプセル媒体のラジカル重合を確実に行わせてナノカプセルを得ることができる。 Moreover, it is preferable that the frequency of the ultrasonic wave when the capsule medium is polymerized be higher than the frequency at the time of the previous dispersion. Thereby, the radical polymerization of the capsule medium can be reliably performed to obtain nanocapsules.
また、カプセル媒体を重合させる時の超音波の周波数を４０Ｈｚ以上とするとよい。これによりカプセル媒体のラジカル重合を確実に行わせることができる。 Further, the frequency of ultrasonic waves when the capsule medium is polymerized is preferably 40 Hz or more. Thereby, radical polymerization of the capsule medium can be surely performed.
また、前記液相を水とし、前記カプセル媒体をスチレンとし、前記蝋相をワックスとするとよい。 The liquid phase may be water, the capsule medium may be styrene, and the wax phase may be wax.
また、前記ナノカプセルは、直径５ｎｍ〜５０００ｎｍとするとよい。 The nanocapsules may have a diameter of 5 nm to 5000 nm.
このように本発明は構成され作用するものであるので、重合開始剤や界面活性剤等の助剤を用いることなく目的とする被封入体となる蝋相を目的とするカプセル媒体によって被覆したナノカプセルを良好にかつ確実に製造することができ、更に生産効率もよく短時間に大量生産可能である等の優れた効果を奏するものである。 Thus, since the present invention is constituted and functions, a nano-phase coated with a target capsule medium on a wax phase to be a target inclusion body without using an auxiliary agent such as a polymerization initiator or a surfactant. Capsule can be produced satisfactorily and surely, and also has excellent effects such as high production efficiency and mass production in a short time.
次に、本発明の実施の形態を図１から図４について説明する。 Next, an embodiment of the present invention will be described with reference to FIGS.
図１は本発明の原理を示している。 FIG. 1 illustrates the principle of the present invention.
本発明においては、まず容器１内に分散用の液相としての溶液２を入れ、この溶液２に対して、重合体からなるナノカプセルを形成するカプセル媒体のモノマーと当該ナノカプセル内に封入される被封入体となる融点以上に加熱された状態の蝋相との混合物３を添加する（図１ａ参照）。 In the present invention, first, a solution 2 as a liquid phase for dispersion is placed in a container 1, and the solution 2 is encapsulated in the nanocapsule with a monomer of a capsule medium forming a nanocapsule made of a polymer. A mixture 3 with a wax phase heated to a temperature equal to or higher than the melting point to be an inclusion body is added (see FIG. 1a).
次に、容器１内の溶液２と混合物３の全体を蝋相の融点以上に加熱しながら比較的低い周波数（例えば、２０ｋＨｚ〜１００ｋＨｚ）の超音波を所定時間照射する。これにより液相である溶液２内にカプセル媒体４によって被封入体５を被覆した微小滴６が分散される（図１ｂ参照）。具体的にはエマルジョンが形成される。分散した微小滴６の直径はナノカプセルの直径とほぼ同じ程度とされている。 Next, an ultrasonic wave having a relatively low frequency (for example, 20 kHz to 100 kHz) is irradiated for a predetermined time while heating the solution 2 and the mixture 3 in the container 1 to the melting point of the wax phase or higher. As a result, the microdroplets 6 in which the encapsulated body 5 is covered with the capsule medium 4 are dispersed in the solution 2 that is in the liquid phase (see FIG. 1b). Specifically, an emulsion is formed. The diameter of the dispersed microdroplets 6 is approximately the same as the diameter of the nanocapsules.
次に、更に蝋相の融点以上に加熱しながら比較的高い周波数（例えば、４０ｋＨｚ以上）超音波を所定時間照射する。ことにより微小滴６のモノマー状のカプセル媒体４がラジカル重合を開始してポリマーとなりナノカプセル７が生産される。 Next, a relatively high frequency (for example, 40 kHz or more) ultrasonic wave is irradiated for a predetermined time while further heating above the melting point of the wax phase. As a result, the monomer-like capsule medium 4 of the microdroplets 6 starts radical polymerization to become a polymer, and nanocapsules 7 are produced.
本発明における前記液相を形成する溶液２としては、ナノカプセル７を形成するカプセル媒体４と被封入体５との性質に対応して分散できる性質を有するものであればよく、例えば、水、水道水、湖水、海水、無機電解質を含む水溶液、グリセリン水溶液等を挙げることができる。 As the solution 2 forming the liquid phase in the present invention, any solution having a property that can be dispersed corresponding to the properties of the capsule medium 4 forming the nanocapsule 7 and the encapsulated body 5 may be used. Examples include tap water, lake water, seawater, an aqueous solution containing an inorganic electrolyte, and a glycerin aqueous solution.
本発明における前記カプセル媒体４としては、製造すべきナノカプセル７の特性に応じて被封入体５となる蝋相を被覆できるものであればよく、例えば、被封入体となる蝋相がワックスであれば、スチレン、イソブチレン等を挙げることができる。その他にカプセル媒体４としては、その他のラジカル重合する高分子等を挙げることができる。 The capsule medium 4 in the present invention is not limited as long as it can coat the wax phase to be encapsulated body 5 according to the characteristics of the nanocapsule 7 to be manufactured. For example, the wax phase to be encapsulated body is a wax. If present, styrene, isobutylene and the like can be mentioned. In addition, examples of the capsule medium 4 include other polymers that undergo radical polymerization.
本発明における前記被封入体５となる蝋相としてのワックスは、ナノカプセル７の特性に応じて選択するとよい。 The wax as the wax phase to be the encapsulated body 5 in the present invention may be selected according to the characteristics of the nanocapsule 7.
混合物３を分散させる場合の超音波の周波数および照射時間としては、混合物３を微小滴６とするために十分なものであればよく、周波数としては例えば２０ｋＨｚ〜１００ｋＨｚ程度がよく、照射時間としては例えば２分〜３０分程度がよい。超音波の周波数が２０ｋＨｚ未満であると分散が行われず、１００ｋＨｚを超えるとラジカル重合が開始されてしまうからである。また、照射時間が２分未満であると分散が行われず、３０分を超えるとラジカル重合が開始されてしまうからである。 The frequency and irradiation time of the ultrasonic waves in the case of dispersing the mixture 3 only need to be sufficient to make the mixture 3 into microdroplets 6, and the frequency is, for example, about 20 kHz to 100 kHz. For example, about 2 to 30 minutes is preferable. This is because dispersion is not performed when the ultrasonic frequency is less than 20 kHz, and radical polymerization is initiated when the frequency exceeds 100 kHz. Moreover, it is because dispersion | distribution will not be performed when irradiation time is less than 2 minutes, and radical polymerization will be started when it exceeds 30 minutes.
微小滴６のモノマー状のカプセル媒体４を重合させる場合の超音波の周波数および照射時間としては、モノマーをポリマーとするためのエネルギーを付与するために十分なものであればよく、周波数としては例えば４０ｋＨｚ以上、好ましくは１００ｋＨｚ以上がよく、照射時間としては例えば３０分〜１２０分程度がよい。超音波の周波数が４０ｋＨｚ未満であるとラジカル重合が開始されないからである。また、照射時間が３０分未満であるとラジカル重合が行われず、１２０分を超えるとラジカル重合が十分に実行されてしまっているからである。 The frequency and irradiation time of the ultrasonic wave when polymerizing the monomer-like capsule medium 4 of the microdroplets 6 may be sufficient as long as it is sufficient to impart energy for making the monomer into a polymer. 40 kHz or more, preferably 100 kHz or more is preferable, and the irradiation time is, for example, about 30 minutes to 120 minutes. This is because radical polymerization is not initiated when the ultrasonic frequency is less than 40 kHz. Moreover, it is because radical polymerization will not be performed when irradiation time is less than 30 minutes, and radical polymerization will fully be performed when it exceeds 120 minutes.
次に、本発明の実施例を説明する。 Next, examples of the present invention will be described.
本実施例においては、カプセル媒体４のモノマーとしてスチレンモノマーを使用し、被封入体５となる蝋相としてパラフィンワックス（Paraffin wax - 140）を使用し、スチレンモノマー／パラフィンワックスの混合物３として、２．０／０．２０（各ｍｌ）を用意した。 In this embodiment, styrene monomer is used as the monomer of the capsule medium 4, paraffin wax (Paraffin wax-140) is used as the wax phase to be the encapsulated body 5, and the mixture 3 of styrene monomer / paraffin wax is 2 0.0 / 0.20 (each ml) was prepared.
溶液２として蒸留水５０ｍｌを用いた。 As the solution 2, 50 ml of distilled water was used.
＜分散＞
まず、各組み合わせに対して、容器１内全体をパラフィンワックスの融点以上の８０℃に加熱し、周波数が４０ｋＨｚの超音波を８分間照射して分散化（エマルジョン化）を行った。
<Dispersion>
First, for each combination, the entire container 1 was heated to 80 ° C. above the melting point of paraffin wax, and ultrasonic waves with a frequency of 40 kHz were irradiated for 8 minutes for dispersion (emulsification).
＜重合＞
本発明の実施例においては、容器１内全体をパラフィンワックスの融点以上の８０℃に継続的に加熱し、更に微小滴６が形成されている容器１に対して周波数が２００ｋＨｚの超音波を１時間照射した。これによりモノマー状のスチレンがラジカル重合してポリスチレンに変化した。
<Polymerization>
In the embodiment of the present invention, the entire inside of the container 1 is continuously heated to 80 ° C., which is equal to or higher than the melting point of paraffin wax, and an ultrasonic wave having a frequency of 200 kHz is applied to the container 1 in which the microdroplets 6 are formed. Irradiated for hours. Thereby, monomeric styrene was radically polymerized and changed to polystyrene.
＜成果物＞
１）ＴＥＭ（透過型電子顕微鏡）観察による粒子の大きさ（図２）
ポリスチレン／パラフィンワックスのナノカプセル７の粒子のＴＥＭ観察を行った。その内容は図２の通りである。
その結果、ポリスチレン／パラフィンワックスのナノカプセル７の微粒子の粒子径は、２００ｎｍ〜１．０μｍであり、形は整っていないもののナノ微粒子のナノカプセル７を確認できた。
２）ＤＳＣ（示差走査熱量計）測定による確認（図３〜図４）
ＴＥＭ観察で確認した微粒子の定性を行うために、ＤＳＣ測定を行った。
図３は本実施例により製造されたナノカプセル７のＤＳＣ測定結果の特性を示し、図４はポリスチレンのＤＳＣ測定結果の特性を示す。
図３に示すナノカプセル７のＤＳＣ測定結果の特性は、図４に示すポリスチレンのＤＳＣ測定結果の特性と相違しているので、ナノカプセル７内にワックスが含まれていることがわかる。従って、ワックスは表面のポリスチレンカプセル内に内包若しくは混合していることがわかる。
３）加温による確認（図５）
次に、図１ｃに示すナノカプセル７が分散している溶液を、ワックスの融点以上であり、かつ、ポリスチレンの融点以下である７５℃以下まで次第に温度を上昇させるように加熱し、温度を上げる前後において溶液の状態の違いを観察した。その結果、溶液の状態に変化が観測されないので、ワックスの溶融が発生していない証左となり、ナノカプセル７が製造されていることがわかった。
<Products>
1) Particle size by TEM (transmission electron microscope) observation (Fig. 2)
TEM observation of the particles of the nanocapsule 7 of polystyrene / paraffin wax was performed. The contents are as shown in FIG.
As a result, the particle size of the fine particles of the polystyrene / paraffin wax nanocapsule 7 was 200 nm to 1.0 μm, and although the shape was not well-defined, the nanoparticle nanocapsule 7 was confirmed.
2) Confirmation by DSC (differential scanning calorimeter) measurement (FIGS. 3 to 4)
In order to qualify the fine particles confirmed by TEM observation, DSC measurement was performed.
FIG. 3 shows the characteristics of the DSC measurement results of the nanocapsules 7 manufactured according to this example, and FIG. 4 shows the characteristics of the DSC measurement results of polystyrene.
Since the characteristics of the DSC measurement result of the nanocapsule 7 shown in FIG. 3 are different from the characteristics of the DSC measurement result of polystyrene shown in FIG. 4, it can be seen that the nanocapsule 7 contains wax. Therefore, it can be seen that the wax is encapsulated or mixed in the surface polystyrene capsule.
3) Confirmation by heating (Fig. 5)
Next, the solution in which the nanocapsules 7 shown in FIG. 1c are dispersed is heated so as to gradually increase the temperature to 75 ° C. or lower which is not lower than the melting point of the wax and not higher than the melting point of polystyrene. The difference in the state of the solution was observed before and after. As a result, since no change was observed in the state of the solution, it was proved that the melting of the wax did not occur, and it was found that the nanocapsule 7 was manufactured.
以上の結果より、重合開始剤無添加で超音波によってラジカル重合させた本実施例の製造方法においてもナノ微粒子となるナノカプセル７を製造することができたことを確認した。 From the above results, it was confirmed that the nanocapsules 7 to be nano-particles could be produced even in the production method of this example in which radical polymerization was performed by ultrasonic waves without addition of a polymerization initiator.
これにより本発明に基づいて、界面開始剤や界面活性剤等の助剤を無添加としてナノカプセル７を製造できることを確認した。 Thereby, based on this invention, it confirmed that nanocapsule 7 could be manufactured without adding adjuvants, such as a surface initiator and surfactant.
なお、本発明は、前述した実施の形態に限定されるものではなく、必要に応じて種々の変更が可能である。例えば、超音波を溶液に付与する場合には、超音波の振動方向を重力方向や水平方向と平行としたり、振動方向を溶液に対して相対移動させるように、振動子若しくは溶液を入れる容器を３６０度の範囲で回転させる等に調整して、超音波エネルギを効率よく付与できるようにするとよい。 In addition, this invention is not limited to embodiment mentioned above, A various change is possible as needed. For example, when applying ultrasonic waves to a solution, a vibrator or a container in which the solution is placed is set so that the vibration direction of the ultrasonic waves is parallel to the gravity direction or the horizontal direction, or the vibration direction is moved relative to the solution. It is preferable to adjust the rotation within a range of 360 degrees so that the ultrasonic energy can be efficiently applied.
１ 容器
２ 溶液
３ 混合物
４ カプセル媒体
５ 被封入体
６ 微小滴
７ ナノカプセル
DESCRIPTION OF SYMBOLS 1 Container 2 Solution 3 Mixture 4 Capsule medium 5 Encapsulate 6 Microdrop 7 Nano capsule
Claims (5)
The nanocapsule manufacturing method according to any one of claims 1 to 4, wherein the nanocapsule has a diameter of 5 nm to 5000 nm.
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| JP2004107097A JP2005288317A (en) | 2004-03-31 | 2004-03-31 | Nanocapsule manufacturing method |
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| JP2004107097A JP2005288317A (en) | 2004-03-31 | 2004-03-31 | Nanocapsule manufacturing method |
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| Publication Number | Publication Date |
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| JP2005288317A true JP2005288317A (en) | 2005-10-20 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100826937B1 (en) | 2006-08-03 | 2008-05-02 | 연세대학교 산학협력단 | Nanocapsules with thermochromic function and preparation method thereof |
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- 2004-03-31 JP JP2004107097A patent/JP2005288317A/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100826937B1 (en) | 2006-08-03 | 2008-05-02 | 연세대학교 산학협력단 | Nanocapsules with thermochromic function and preparation method thereof |
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