JPH0360731A - Production of microcapsule - Google Patents
Production of microcapsuleInfo
- Publication number
- JPH0360731A JPH0360731A JP1196122A JP19612289A JPH0360731A JP H0360731 A JPH0360731 A JP H0360731A JP 1196122 A JP1196122 A JP 1196122A JP 19612289 A JP19612289 A JP 19612289A JP H0360731 A JPH0360731 A JP H0360731A
- Authority
- JP
- Japan
- Prior art keywords
- core material
- curing resin
- membrane material
- microcapsule
- electron
- 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.)
- Granted
Links
- 239000003094 microcapsule Substances 0.000 title claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 239000011162 core material Substances 0.000 claims abstract description 14
- 239000000463 material Substances 0.000 claims abstract description 12
- 239000012528 membrane Substances 0.000 claims abstract description 11
- 229920005989 resin Polymers 0.000 claims abstract description 11
- 239000011347 resin Substances 0.000 claims abstract description 11
- 239000000126 substance Substances 0.000 claims abstract description 9
- 238000010894 electron beam technology Methods 0.000 claims abstract description 5
- 239000008346 aqueous phase Substances 0.000 claims description 3
- 239000010419 fine particle Substances 0.000 claims description 3
- 230000001678 irradiating effect Effects 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims 1
- 239000006185 dispersion Substances 0.000 abstract description 2
- 239000000975 dye Substances 0.000 abstract description 2
- 238000003848 UV Light-Curing Methods 0.000 abstract 2
- 238000001227 electron beam curing Methods 0.000 abstract 2
- 230000003028 elevating effect Effects 0.000 abstract 1
- 238000012643 polycondensation polymerization Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000012696 Interfacial polycondensation Methods 0.000 description 6
- 150000004291 polyenes Chemical class 0.000 description 5
- 229920006295 polythiol Polymers 0.000 description 5
- 239000011257 shell material Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 4
- 238000006068 polycondensation reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 2
- -1 and cooling. method Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- AXISYYRBXTVTFY-UHFFFAOYSA-N Isopropyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC(C)C AXISYYRBXTVTFY-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（ａ）産業上の利用分野
本発明は薬剤、染料等を包み込んで、直接薬剤等が他の
物質と接触するのを防ぐと共に、品質の保全、長期安定
性能を維持するための、マイクロカプセルの製造に関す
るものである。Detailed Description of the Invention (a) Industrial Application Field The present invention wraps drugs, dyes, etc. to prevent the drugs, etc. from coming into direct contact with other substances, and maintains quality and long-term stable performance. The present invention relates to the production of microcapsules.
（ｂ）従来の技術
従来よりこの種のマイクロカプセルの製造法は、相分離
法と界面沈澱法の物理化学的製造法と、界面重縮合法に
代表される化学的製造法と、融解分散冷却法、粉床法、
気中懸７＠被覆法の機械的製造法の３つの製造法があっ
て、例えば特開昭６２−１４５１号、特開昭６２−７４
４０号、特開昭６２−３８２３７号、特開昭６２−５７
６４４号等の提案がなされている。(b) Conventional technology Conventionally, methods for manufacturing this type of microcapsules include physicochemical manufacturing methods such as phase separation and interfacial precipitation, chemical manufacturing methods such as interfacial polycondensation, and melting, dispersion, and cooling. method, powder bed method,
There are three mechanical manufacturing methods: air suspension 7@coating method; for example, JP-A-62-1451 and JP-A-62-74.
No. 40, JP-A-62-38237, JP-A-62-57
Proposals such as No. 644 have been made.
この発明はこの中の化学的製造法に属するもので、界面
重縮合法に係るものであるが、従来この界面重縮合法は
、液状の芯物質中に、成る特定の単量体を熔解し、この
溶液へ芯物質を微粒子状に分散させた別の単量体の液と
、重縮合触媒を加え又は加えないで微粒子の表面で重縮
合反応を生じしめ、高分子膜を生成させマイクロカプセ
ル化を行ってきた。この方法は温度及び反応時間のコン
トロールが極めて重要で、定量的に重縮合反応を行う為
の工夫が種々行われた。この種の１１体としてポリイミ
ド、ポリアミド、ポリエステル、ポリウレタン、ポリ尿
素等を生成するものが用いられるが、反応時間が何れも
数時間から十数時間におよび、又反応熱の発生もあって
生産に支障を来すことが往々にしてありこの改良が望ま
れる処であった。This invention belongs to the chemical production method among these, and is related to the interfacial polycondensation method. Conventionally, this interfacial polycondensation method involves melting a specific monomer in a liquid core material. , A polycondensation reaction is caused on the surface of the fine particles by adding or not adding a polycondensation catalyst to this solution with another monomer liquid in which the core substance is dispersed in the form of fine particles, and a polymer film is generated to form microcapsules. has been transformed. Control of temperature and reaction time is extremely important in this method, and various efforts have been made to quantitatively carry out the polycondensation reaction. Those that produce polyimide, polyamide, polyester, polyurethane, polyurea, etc. are used as this type of 11-component, but the reaction time for all of them ranges from several hours to more than 10 hours, and the production is difficult due to the generation of reaction heat. This often causes problems and improvements are desired.
（ｃ）発明が解決しようとする問題点
従来のマイクロカプセルの製造法の中で、特に化学工場
で生産されるものは、上記の如くであって、本発明が特
に解決しようとする目的にしているのは、界面重縮合反
応における時間の短縮と温度コントロールであって、良
質のマイクロカプセルの生産を能率良く行うことにある
。(c) Problems to be Solved by the Invention Among the conventional manufacturing methods for microcapsules, those produced in chemical factories in particular are as described above, and the problems to be solved by the present invention are as follows. What is needed is to shorten the time and control the temperature in the interfacial polycondensation reaction, and to efficiently produce high-quality microcapsules.
（ｄ）問題点を解決するための手段
本発明は界面重縮合反応に於ける時間の短縮と、温度の
制御を簡単に解決するために、加熱、触媒、添加等で重
量体の重縮合反応を行わず、代わりに紫外線又は電子線
で重縮合可能な紫外線硬化型樹脂を使用して問題の解決
を計った。更に紫外線硬化型樹脂としてはポリアクリル
型、ポリエステル型、ポリウレタン型、ポリエンポリチ
オール型、エポキシ型、スピロアセクール型等が有り特
に水相にて紫外線を照射する為水に不溶なタイプの選定
が要求される。この発明では耐水性に優れた例えばポリ
エンポリチオール型を選定してマイクロカプセル製造時
の皮殻（膜）とした、即ち水相で界面重縮合反応を短時
間で、而も温度上昇させずに定量的に行う為に、耐水型
の紫外線硬化型樹脂を用いた事により上記の問題点を容
易に解決出来たものである。(d) Means for Solving the Problems The present invention aims to shorten the time and easily control the temperature in the interfacial polycondensation reaction. Instead, we attempted to solve the problem by using an ultraviolet curable resin that can be polycondensed with ultraviolet rays or electron beams. Furthermore, UV-curable resins include polyacrylic type, polyester type, polyurethane type, polyene polythiol type, epoxy type, spiroacecool type, etc., and in particular, it is necessary to select a type that is insoluble in water since UV rays are irradiated in the aqueous phase. be done. In this invention, for example, a polyene polythiol type with excellent water resistance was selected to be used as the shell (membrane) for manufacturing microcapsules.In other words, the interfacial polycondensation reaction was carried out in the aqueous phase in a short time and quantified without increasing the temperature. By using a water-resistant ultraviolet curing resin, the above problems can be easily solved.
（ｅ）作用
この発明によってマイクロカプセルを製造する時の状態
は、通常膜物質に各種単量体を用いてマイクロカプセル
をつくる場合に比べ、芯物質を樹脂溶液に分散させるの
は同じであっても、紫外線を照射することにより瞬時、
即ち１〜２分間で反応が終了する為、温度の上昇は全く
考慮に入れなくても良く、生産のスピードがアップし、
又構造式による反応に対する未反応の末端基が残ること
がなく反応は定量的に完了する。(e) Effect When manufacturing microcapsules according to the present invention, the conditions are the same as those in which the core material is dispersed in a resin solution, compared to the case where microcapsules are manufactured using various monomers in the membrane material. Also, by irradiating ultraviolet rays,
In other words, since the reaction completes in 1 to 2 minutes, there is no need to take temperature increases into account, speeding up production.
Further, the reaction according to the structural formula is completed quantitatively without leaving any unreacted end groups.
（ｆ）実施例 以下に実施例を示して本発明の詳細な説明する。(f) Examples The present invention will be described in detail below with reference to Examples.
実施例−１
皮殻（膜）材 ポリエンポリチオール ４０ｇ（旭
電化工業製Ｂ Ｙ−３０５）
芯物質 ミリスチン酸イソプロピルエステル０ｇ
（ミョシ油脂 ＭＩＰ）
を水３００ｍ／巾に没入し、攪拌機にて攪拌した状態に
て、紫外線照射装置（ウシオ電（幾製）を作動させ照射
ランプ（８０ワット／ｃ１１１メタハライド型管長＝ｌ
Ｑｃｍ）をｌＱｃｍの位置に近すけ２分間照射をし、皮
殻（膜）材のポリエンポリチオールを硬化させて反応は
終了する。水洗風乾の後芯物質ミリスチン酸イソプロピ
ル（脂肪酸エステル）が封入されたマイクロカプセル約
５９ｇを得た。Example-1 Shell (membrane) material 40 g of polyene polythiol (BY-305 manufactured by Asahi Denka Kogyo) Core material 0 g of myristate isopropyl ester (Miyoshi oil MIP) immersed in water 300 m/width and stirred with a stirrer At the time, an ultraviolet irradiation device (manufactured by Ushio Den Co., Ltd.) was activated, and an irradiation lamp (80 watts/c111 metahalide type tube length = l) was used.
Qcm) is irradiated for 2 minutes at a position of 1Qcm to harden the polyene polythiol of the shell (membrane) material and the reaction is completed. After washing with water and air drying, about 59 g of microcapsules encapsulating the core substance isopropyl myristate (fatty acid ester) were obtained.
実施例−２
皮殻（欣）材 ポリエンポリチオール ４０ｇ（旭
電化工業製ＢＹ−３０５）
芯物質 ステアリン酸 ２０ｇ（ミ
ヨシ油脂製）
を９０℃の温水３００ｍｌ中に投入し、攪１１３機にて
攪拌しつ＼紫外線照射装置（ウシオ電機製）を作動し、
照射ランプ（実施例と同じ）を１０ｃｍの位置に近ずけ
、２分間照射をしステアリン酸（Ｍ処刑）を芯物質とし
たマイクロカプセルを水洗乾燥後５９ｇを得た。Example-2 Shell material: 40 g of polyene polythiol (BY-305 manufactured by Asahi Denka Kogyo) and core material: 20 g of stearic acid (manufactured by Miyoshi Oil Co., Ltd.) were added to 300 ml of 90°C warm water and stirred using a stirrer. Activate the ultraviolet irradiation device (manufactured by Ushio Inc.),
An irradiation lamp (same as in Example) was brought close to the position of 10 cm, and irradiation was performed for 2 minutes to obtain 59 g of microcapsules containing stearic acid (M-Jyoshi) as a core material after washing with water and drying.
上記実施例−〇及び実施例−２、何れも紫外線照射によ
る反応終結時間は２分間であり、反応系の温度上昇も認
められなかった。In both Example-0 and Example-2, the reaction termination time due to ultraviolet irradiation was 2 minutes, and no rise in temperature of the reaction system was observed.
（ｇ）発明の効果
本発明は、従来の化学的マイクロカプセルの製造法の弱
点である、皮殻（膜）物質を形成する単量体の重縮合反
応が時間と温度の点で量産化と、品質の安定度に問題が
あったのに代わり、紫外線硬化型樹脂を配したところ時
間の点及び温度上昇の点で極めて効果ある解決を見た。(g) Effects of the invention The present invention makes it possible to mass-produce the polycondensation reaction of monomers that form the shell (membrane) material, which is a weak point of the conventional chemical microcapsule manufacturing method, in terms of time and temperature. However, when there was a problem with quality stability, we used ultraviolet curable resin, which was an extremely effective solution in terms of time and temperature rise.
又本発明は紫外線を遮断しない状況下で行うことを前提
にしているが、紫外線を透過しない容器中行う場合紫外
線に代わり電子線を照射しても効果は同じである。Furthermore, although the present invention is based on the premise that the treatment is carried out under conditions where ultraviolet rays are not blocked, the same effect can be obtained even if electron beams are irradiated instead of ultraviolet rays when carried out in a container that does not transmit ultraviolet rays.
Claims (1)
化型樹脂を用い、この芯物質と膜物質の両者を水相で分
散させながら、紫外線又は電子線を照射して該膜物質を
硬化させて、芯物質微粒子を球状膜物質の中に閉じ込め
て、カプセルを形成することを特徴とするマイクロカプ
セルの製造法。An ultraviolet curable resin or an electron beam curable resin is used as the film material surrounding the core material, and while both the core material and the film material are dispersed in an aqueous phase, the film material is cured by irradiating ultraviolet rays or electron beams. A method for producing a microcapsule, comprising: trapping fine particles of a core substance in a spherical membrane substance to form a capsule.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1196122A JP2928926B2 (en) | 1989-07-27 | 1989-07-27 | Manufacturing method of microcapsules |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1196122A JP2928926B2 (en) | 1989-07-27 | 1989-07-27 | Manufacturing method of microcapsules |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0360731A true JPH0360731A (en) | 1991-03-15 |
| JP2928926B2 JP2928926B2 (en) | 1999-08-03 |
Family
ID=16352608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1196122A Expired - Fee Related JP2928926B2 (en) | 1989-07-27 | 1989-07-27 | Manufacturing method of microcapsules |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2928926B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003059503A1 (en) * | 2002-01-08 | 2003-07-24 | Analytical Research Systems | Hydrocapsules and method of preparation |
| US6780507B2 (en) | 2000-02-09 | 2004-08-24 | Analytical Research Systems, Inc. | Hydrocapsules and method of preparation thereof |
| CN109679585A (en) * | 2018-12-18 | 2019-04-26 | 同济大学 | A kind of phase-change microcapsule and preparation method thereof using photocuring processes synthesis |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5579597B2 (en) * | 2008-04-16 | 2014-08-27 | 森下仁丹株式会社 | Thermal storage seamless capsule and manufacturing method thereof |
-
1989
- 1989-07-27 JP JP1196122A patent/JP2928926B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6780507B2 (en) | 2000-02-09 | 2004-08-24 | Analytical Research Systems, Inc. | Hydrocapsules and method of preparation thereof |
| WO2003059503A1 (en) * | 2002-01-08 | 2003-07-24 | Analytical Research Systems | Hydrocapsules and method of preparation |
| CN109679585A (en) * | 2018-12-18 | 2019-04-26 | 同济大学 | A kind of phase-change microcapsule and preparation method thereof using photocuring processes synthesis |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2928926B2 (en) | 1999-08-03 |
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Free format text: JAPANESE INTERMEDIATE CODE: R250 |
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