JPS5946124A - Preparation of microcapsule - Google Patents
Preparation of microcapsuleInfo
- Publication number
- JPS5946124A JPS5946124A JP57155538A JP15553882A JPS5946124A JP S5946124 A JPS5946124 A JP S5946124A JP 57155538 A JP57155538 A JP 57155538A JP 15553882 A JP15553882 A JP 15553882A JP S5946124 A JPS5946124 A JP S5946124A
- Authority
- JP
- Japan
- Prior art keywords
- substance
- core material
- powder
- wall
- temp
- 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 29
- 239000000843 powder Substances 0.000 claims abstract description 39
- 239000000126 substance Substances 0.000 claims abstract description 31
- 238000003756 stirring Methods 0.000 claims abstract description 20
- 238000007710 freezing Methods 0.000 claims abstract 2
- 230000008014 freezing Effects 0.000 claims abstract 2
- 239000011162 core material Substances 0.000 claims description 44
- 239000000463 material Substances 0.000 claims description 31
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- 238000010298 pulverizing process Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 abstract description 19
- 230000001070 adhesive effect Effects 0.000 abstract description 10
- 239000000853 adhesive Substances 0.000 abstract description 9
- 238000005054 agglomeration Methods 0.000 abstract description 6
- 230000002776 aggregation Effects 0.000 abstract description 6
- 230000008018 melting Effects 0.000 abstract description 6
- 238000002844 melting Methods 0.000 abstract description 6
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 abstract description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract 1
- 230000006866 deterioration Effects 0.000 abstract 1
- 238000005538 encapsulation Methods 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 239000002245 particle Substances 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
- 239000002775 capsule Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 239000001993 wax Substances 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- -1 fatty acid esters Chemical class 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 230000004075 alteration Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000004925 denaturation Methods 0.000 description 2
- 230000036425 denaturation Effects 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical compound OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O IMQLKJBTEOYOSI-GPIVLXJGSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- IMQLKJBTEOYOSI-UHFFFAOYSA-N Phytic acid Natural products OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 238000005354 coacervation Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- GYPBUYJSHBFNEJ-UHFFFAOYSA-L copper;hexadecanoate Chemical compound [Cu+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O GYPBUYJSHBFNEJ-UHFFFAOYSA-L 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229910000743 fusible alloy Inorganic materials 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- HSEMFIZWXHQJAE-UHFFFAOYSA-N hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(N)=O HSEMFIZWXHQJAE-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000012169 petroleum derived wax Substances 0.000 description 1
- 235000019381 petroleum wax Nutrition 0.000 description 1
- 229940068041 phytic acid Drugs 0.000 description 1
- 235000002949 phytic acid Nutrition 0.000 description 1
- 239000000467 phytic acid Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000007779 soft material Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- LPEBYPDZMWMCLZ-CVBJKYQLSA-L zinc;(z)-octadec-9-enoate Chemical compound [Zn+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LPEBYPDZMWMCLZ-CVBJKYQLSA-L 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesive Tapes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Formation And Processing Of Food Products (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Dispersion Chemistry (AREA)
- Color Printing (AREA)
- General Preparation And Processing Of Foods (AREA)
- Jellies, Jams, And Syrups (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
【発明の詳細な説明】
この発明は、特に常温付近で液体または粘着性を有する
物質または軟質物質をマイクロカプセル化する方法に凹
する。DETAILED DESCRIPTION OF THE INVENTION The present invention is particularly directed to a method for microencapsulating a substance or a soft substance that is liquid or sticky at room temperature.
マイクロカプセルは感圧複写紙をはじめ、医薬、農薬、
香料などに広く利用されている。Microcapsules are used in pressure-sensitive copying paper, pharmaceuticals, agricultural chemicals,
It is widely used as a fragrance.
従来の代表的なマイクロカプセルの製造法としては、１
．コアセルベーション法、２．昇面重合法、３．ｉｎ
ｓｉｔｕ重合法、４．液中乾燥法、５．融解分散冷却法
、６．オリフィス法、７．スプレードライング法、８．
気中懸濁被覆法、９．無機質壁マイクロカプセル化法な
どがある。ところがこのような製造法を用いて、水、有
機溶剤、水あめ、糊、粘着剤、接着剤などの常温では液
体または粘着性を有する物質もしくは軟質物質をマイク
ロカプセル化する場合には次のような欠点がある。すな
わち、１〜５の方法では分散媒中に上記物質よりなる芯
物質を分散させる際、芯物質が粘着性を有する場合には
芯物質粒子が付着しあって集塊化する。また、芯物質と
高分子溶液とのぬれおよび比重の調整が必要となり、作
業が面倒でしかも仕上ったカプセルの特性もよくない。Typical conventional microcapsule manufacturing methods include 1.
．． Coacervation method, 2. Surface elevation polymerization method, 3. in
Situ polymerization method, 4. In-liquid drying method, 5. Melting dispersion cooling method, 6. Orifice method, 7. Spray drying method, 8.
Air suspension coating method, 9. Examples include inorganic wall microencapsulation. However, when using this manufacturing method to microcapsule substances that are liquid or sticky at room temperature, such as water, organic solvents, starch syrup, glue, adhesives, or soft substances, the following steps are required. There are drawbacks. That is, in methods 1 to 5, when a core material made of the above substance is dispersed in a dispersion medium, if the core material has adhesive properties, the core material particles adhere to each other and form agglomerates. In addition, it is necessary to adjust the wetting of the core material and the polymer solution and the specific gravity, which is a cumbersome process and the properties of the finished capsules are also poor.
また、６の方法はミクロンオーダーのカプセルを作りに
くく、生産効率も低い。さらに５、７、８の方法はトナ
ーのカプセル化に使用されているが、均一な膜厚、完全
被覆のカプセルを作りにくいうえにトナーより粘着性の
強い物質の場合には集塊化を招く。また、１〜８の方法
は水や有機溶剤を使用するので、水や有機溶剤に浸され
たり、反応する芯物質をカプセル化することができない
うえ、有機溶剤の後処理が面倒であり、カプセルを粉体
として取り出すためには乾燥が必要であり、火災、爆発
の危険性がある。Furthermore, method 6 is difficult to produce micron-order capsules and has low production efficiency. Furthermore, methods 5, 7, and 8 are used to encapsulate toner, but it is difficult to produce capsules with uniform film thickness and complete coverage, and in the case of substances that are more adhesive than toner, they lead to agglomeration. . In addition, since methods 1 to 8 use water or organic solvents, it is not possible to encapsulate the core substance that is immersed or reacts in water or organic solvents, and post-treatment of the organic solvent is troublesome. Drying is required to extract it as a powder, which poses the risk of fire and explosion.
さらに、９の方法は芯物質が軟質物質の場合は芯物質内
部に多量の壁物質が混入し、カプセルというよりはむし
ろ混合物になりやすい、
このように１〜９の方法では、いずれの場合も満足のゆ
くマイクロカプセルを製造することができなかった。Furthermore, in method 9, if the core material is a soft material, a large amount of wall material mixes inside the core material, which tends to result in a mixture rather than a capsule. It was not possible to produce satisfactory microcapsules.
この発明は、上記事情に鑑みてなされたもので、常温で
液体または粘着性を有する物質もしくは軟質物質あるい
は水や有機溶剤に浸されるかこれと反応する物質等を簡
単に高収率でかつ安全にマイクロカプセル化できしかも
上記物質の変質、変性が生じることがないマイクロカプ
セルの製造法を提供することを目的とするものである。This invention was made in view of the above circumstances, and it is possible to easily and efficiently prepare substances that are liquid or sticky at room temperature, soft substances, or substances that are immersed in or react with water or organic solvents in a high yield. The object of the present invention is to provide a method for producing microcapsules that can be safely microencapsulated without causing any alteration or denaturation of the above-mentioned substances.
以下、この発明を詳しく説明する。This invention will be explained in detail below.
この発明の製造法に用いられる芯物質としては、水溶液
、水分散液、粘着剤、接着剤、塗料、有機溶剤などの、
粉状とした場合に常温付近（０℃〜５０℃）では液体に
なるかあるいは集塊化を起し粉状を維持できない物質が
用いられる。Core substances used in the production method of this invention include aqueous solutions, aqueous dispersions, pressure-sensitive adhesives, adhesives, paints, organic solvents, etc.
When made into a powder, a substance is used that becomes liquid or agglomerates at around room temperature (0° C. to 50° C.) and cannot maintain its powder state.
また、この芯物質を被覆する壁物質としては、芯物質と
の相互関係によって決められるが、一般には次のような
物質が用いられる。まず、ラウリン酸、ミリスチン酸、
ステアリン酸、オレイン酸、などの高級脂肪酸、ラウリ
ルアルコール、パルミチルアルコール、ステアリルアル
コールなどの高級アルコール、パルミチン酸アミド、ス
テアリン酸アミド、オレイン酸アミドなどの高級脂肪酸
アミド、グリセリン脂肪酸エステルなどの高級脂肪酸エ
ステル、ステアリン酸アルミニウム、ステアリン酸亜鉛
、ステアリン酸カルシウム、オレイン酸鉛、オレイン酸
亜鉛、パルミチン酸銅などの高級脂肪酸金属塩、カルナ
ウパワックス、パラフィンワックス、ビーズワックス、
木ロウ、牛脂ワックス、カルデラワックス、ポリエチレ
ンワックス、酸化パラフィンワックスなどの天然および
石油系ワックス、ロジン系樹脂、テルペン系樹脂など天
然および合成樹脂、牛脂などの固形油脂、ゼラチンゼリ
ー、バター、メルトタイプチーズなどの食品、ワッド合
金、ニュートン合金などの易融合金などが挙げられる。The wall material covering the core material is determined depending on the relationship with the core material, but the following materials are generally used. First, lauric acid, myristic acid,
Higher fatty acids such as stearic acid and oleic acid, higher alcohols such as lauryl alcohol, palmityl alcohol, and stearyl alcohol, higher fatty acid amides such as palmitic acid amide, stearic acid amide, and oleic acid amide, and higher fatty acid esters such as glycerin fatty acid ester. , higher fatty acid metal salts such as aluminum stearate, zinc stearate, calcium stearate, lead oleate, zinc oleate, copper palmitate, carnaupa wax, paraffin wax, beeswax,
Natural and petroleum waxes such as wood wax, tallow wax, caldera wax, polyethylene wax, and oxidized paraffin wax, natural and synthetic resins such as rosin resins and terpene resins, solid oils and fats such as beef tallow, gelatin jelly, butter, and melt-type cheese. Examples include foods such as , easily fusible alloys such as wad alloy and Newton's alloy.
そして、これら壁物質は、常温付近では固形であり、さ
らに後述するように低温度での芯物質との混合撹拌の際
、その温度で芯物質より微粒化し、さらに混合撹拌の際
に生ずる粒子間の摩擦等によって粒子面に発生する局所
熱の温度における壁物質の粘度が芯物質の粘度より低い
ことが必要である。なおこれらの粘度の比較は壁物質の
融点又は軟化点付近の温度で行なわれ、そして本発明の
方法での壁物質は発生する局所熱と凹連して融点又は軟
化点が約２００℃以下である物質を使用して行なうこと
が好ましい。These wall materials are solid at around room temperature, and as will be described later, when mixed with the core material at low temperatures, they become finer than the core material at that temperature, and furthermore, the particles between particles that occur during the mixing and stirring occur. It is necessary that the viscosity of the wall material be lower than the viscosity of the core material at the temperature of local heat generated on the particle surface due to friction or the like. These viscosities are compared at temperatures near the melting point or softening point of the wall material, and the wall material in the method of the present invention has a melting point or softening point of about 200° C. or less due to the local heat generated. Preferably, this is done using a certain substance.
つぎに、マイクロカプセル化について説明する。Next, microencapsulation will be explained.
まず、芯物質を液体窒素などの冷熱を利用して凍結し、
この状態で粉末化する。この時の温度は、芯物質の種類
によって異り、水溶液、水分散液などでは−２０℃程度
であり、粘着剤、接着剤などのように粘着性あるいは易
集塊性のものでは−５０〜−８０℃程度である。そして
、粉砕機の回転数（粉砕速度）や粉砕温度を適宜調節し
て平均粒径１〜１０００μｍの粉末とする。First, the core material is frozen using cold heat such as liquid nitrogen.
Powder it in this state. The temperature at this time varies depending on the type of core material, and is around -20°C for aqueous solutions and dispersions, and -50°C for sticky or easily agglomerated materials such as adhesives and adhesives. The temperature is about -80°C. Then, the rotation speed (pulverization speed) and the crushing temperature of the pulverizer are appropriately adjusted to obtain a powder having an average particle size of 1 to 1000 μm.
ついで、この粉末を低温度に保って集塊化あるいは融解
を起さないように維持しつつ、上記壁物質を加えて混合
撹拌し、マイクロカプセル化する。Next, while maintaining this powder at a low temperature to prevent agglomeration or melting, the above-mentioned wall material is added and mixed and stirred to form microcapsules.
この混合撹拌には、液化窒素冷却ジャケットを装備した
カッター付高速撹拌機を用いることが好ましく、撹拌条
件は撹拌速度５，０００〜２０，０００ｒｐｍ、撹拌時
間１〜１０分である。特に、このタイプの撹拌機を用い
た場合、上記連結粉砕もこの装置内で行え工程上有利と
なる。その他、混合撹拌にはボールミル、カッター付撹
拌機、アトライターなども用いることができる。撹拌時
の温度は、上記連結粉砕時の温度と同程度であり、摩擦
熱による温度上昇を防止するために、撹拌機には液化窒
素等の冷却剤を通じ、冷却を行いつづける必要がある。For this mixing and stirring, it is preferable to use a high-speed stirrer with a cutter equipped with a liquefied nitrogen cooling jacket, and the stirring conditions are a stirring speed of 5,000 to 20,000 rpm and a stirring time of 1 to 10 minutes. In particular, when this type of stirrer is used, the above-mentioned connected pulverization can also be performed within this device, which is advantageous in terms of the process. In addition, a ball mill, a stirrer with a cutter, an attritor, etc. can also be used for mixing and stirring. The temperature during stirring is about the same as the temperature during the above-mentioned connected pulverization, and in order to prevent temperature rise due to frictional heat, it is necessary to continue cooling the stirrer by passing a coolant such as liquefied nitrogen.
また、芯物質の粉末と壁物質との混合比は、芯物質の粉
末の形状によっても左右され、粉末が球状の場合には壁
物質は少量で済むが、通常は芯物質の粉末１００重量部
に対して壁物質０．５〜５０重量部とされる。さらに、
得られるマイクロカプセルの粒径は、芯物質の粉末の粒
径と壁物質による膜厚によって決められるため、連結粉
砕の条件、芯物質と壁物質との混合量比、混合撹拌の条
件によって任意に調節でき、平均粒径１〜１５００μｍ
のマイクロカプセルが良好に得られる。この混合撹拌操
作中、壁物質の粉末はこの撹拌時の温度において、上述
のように芯物質よりも微粒化されやすいので、この芯物
質と壁物質の両者が衝突した際、芯物質の表面により微
粒化した壁物質が物理的に付着した後更に両者の衝突表
面が局部的に摩擦熱が発生し加熱され、壁物質の粘度が
芯物質の粘度より低いことにより壁物質が流動して芯物
質の粉末の表面に塗りつけられ、これによって芯物質の
粉末は壁物質で被覆されることになる。The mixing ratio of the core material powder and the wall material also depends on the shape of the core material powder; if the powder is spherical, a small amount of wall material is required, but usually 100 parts by weight of the core material powder is used. The amount of wall material is 0.5 to 50 parts by weight. moreover,
The particle size of the obtained microcapsules is determined by the particle size of the core material powder and the film thickness of the wall material, so it can be arbitrarily determined by the conditions of connected crushing, the mixing ratio of the core material and wall material, and the mixing and stirring conditions. Adjustable, average particle size 1-1500μm
microcapsules can be obtained satisfactorily. During this mixing and stirring operation, the powder of the wall material is more likely to be atomized than the core material at the stirring temperature, so when the core material and the wall material collide, the surface of the core material After the atomized wall material physically adheres to the surface, frictional heat is generated locally on the collision surface of the two, and the wall material flows and the core material flows due to the viscosity of the wall material being lower than that of the core material. The powder of the core material is coated with the wall material.
このようにして得られたマイクロカプセルは、芯物質の
粉末が壁物質で完全に被覆され常温になってもサラサラ
した流動性の良い粉末となる。In the microcapsules thus obtained, the core material powder is completely covered with the wall material, and the microcapsules remain smooth and fluid even at room temperature.
また、得られるマイクロカプセルの流動性を一層高めた
い場合あるいは壁物質による被覆をより完全にするため
に上記混合撹拌時の次のような平均粒径約１００μｍ以
下の微粉末を少量加えることもできる。微粉末としては
、シリカ微粉、各種ベントナイト、酸化アルミニウム、
カーボンブラック、炭酸カルシウム、タルク、カオリン
、酸化チタン、セラミック粉末、フイチン酸およびその
金属塩、ポリエチレン、ナイロン、メタアクリレートな
どの合成樹脂微粉末、でん粉ならびにこれら粉末を表面
処理した微粉末が挙げられる。この後粉末の添加量は、
芯物質の粉末１００重量部に対して０．５〜５重量部で
十分である。In addition, if it is desired to further increase the fluidity of the obtained microcapsules or to make the coating with the wall substance more complete, a small amount of fine powder having an average particle size of about 100 μm or less can be added during the above mixing and stirring process. . Fine powders include silica fine powder, various bentonites, aluminum oxide,
Examples include carbon black, calcium carbonate, talc, kaolin, titanium oxide, ceramic powder, phytic acid and its metal salts, synthetic resin fine powder such as polyethylene, nylon, methacrylate, starch, and fine powder obtained by surface treatment of these powders. After this, the amount of powder added is
0.5 to 5 parts by weight per 100 parts by weight of the core material powder is sufficient.
なお、芯物質は、その粘度が高い程マイクロカプセルの
形状保磁力がすぐれて安定性がよいので、低粘度の芯物
質の場合にはこれに充填剤、増粘剤、ゲル化剤などを加
えて増粘もしくはゲル化させておくことが好ましい。ま
た、上記微粉末で芯物質の粉末の表面を補強するように
してもよい。Note that the higher the viscosity of the core material, the better the microcapsule shape coercive force and stability, so in the case of a low-viscosity core material, fillers, thickeners, gelling agents, etc. may be added to it. It is preferable to increase the viscosity or gelatinization. Further, the surface of the core material powder may be reinforced with the fine powder.
このようなマイクロカプセルの製造法によれば、芯物質
を凍結粉砕して粉末化し、これに壁物質を加えて低温度
下で混合撹拌するものであるので、製造途中で芯物質お
よび壁物質のロスが全く無く、収率１００％でマイクロ
カプセル化でき、工程が簡単で短時間で製造でき、製造
装置も撹拌機のみでよく、したがって製造コストが著る
しく低いものとなる。また、すべての工程が低温化で行
われるので、芯物質および壁物質の変性変質がなく不安
定な芯物質をもマイクロカプセル化できる。さらに、水
や有機溶剤を使用する従来法に比べて、乾燥工程や廃液
処理が不要となり、かつ作業の安全性も高い。マイクロ
カプセルの粒径の調整が任さらに、このカプセルの流動
性を高めるため、シリカ微粉（平均粒径１６μｍ）を２
重量部加えてカッター付撹拌機中で０℃以下で混合撹拌
を行った。撹拌速度２０，０００ｒｐｍ撹拌時間１５秒
。According to the manufacturing method of such microcapsules, the core material is freeze-pulverized and powdered, and the wall material is added to this and mixed and stirred at low temperature. There is no loss at all, microcapsules can be formed with a yield of 100%, the process is simple and can be produced in a short time, and the production equipment requires only a stirrer, resulting in significantly low production costs. Furthermore, since all steps are performed at low temperatures, there is no denaturation or alteration of the core material or wall material, and even unstable core materials can be microencapsulated. Furthermore, compared to conventional methods that use water or organic solvents, there is no need for a drying process or waste liquid treatment, and the work is highly safe. In addition to controlling the particle size of the microcapsules, in order to increase the fluidity of the capsules, 20% of fine silica powder (average particle size 16 μm) was added.
Parts by weight were added and mixed and stirred at 0° C. or lower in a stirrer equipped with a cutter. Stirring speed: 20,000 rpm, stirring time: 15 seconds.
これにより、常温にもどしてもサラサラで流動性の良好
なステアリルアルコール−シリカ微粉末混合壁を有する
粘着剤のマイクロカプセルが収率１００％で得られた。As a result, pressure-sensitive adhesive microcapsules having stearyl alcohol-silica fine powder mixed walls that were smooth and had good fluidity even when returned to room temperature were obtained in a yield of 100%.
このマイクロカプセルを適量ステンレススチール板上で
散布し、別のステンレススチール板をこれに当てて加圧
したところ、ステンレススチール板は互いに弱粘着した
。さらに、これを１００℃で５秒間加熱し圧着したとこ
ろ、強力に粘着した。When an appropriate amount of these microcapsules was dispersed on a stainless steel plate and another stainless steel plate was applied to it and pressurized, the stainless steel plates slightly adhered to each other. Furthermore, when this was heated at 100° C. for 5 seconds and pressure bonded, it became strongly adhesive.
〔実施例２〕
水あめを−５０℃に連結したのちカッター付撹拌機で粉
砕し、平均粒径５０μｍの連結粉末を得た。この粉末１
００重量部を集塊化しない温度である−５０℃に保持し
つつ、ステアリルアルコール１５重量部とともにカッタ
ー付撹拌機にて撹拌速度２０，０００ｒｐｍ撹拌時間５
分にて混合撹拌し、マイクロカプセルを得た。撹拌終了
時の温度は−３０℃であった。このマイクロカプセルに
疎水性シリカ微粉（商品名 アエロジル Ｒ９７２）２
重量部を加えて、−１０℃以下で２０，０００ｒｐｍで
１５秒間撹拌した。これにより常温にもどしてもサラサ
ラで流動性にすぐれたステアリルアルコール シリカ微
粉混合壁を有する水あめのマイクロカプセルが収率１０
０％で得られた。[Example 2] Starch syrup was connected to −50° C. and then ground with a stirrer equipped with a cutter to obtain a connected powder with an average particle size of 50 μm. This powder 1
While maintaining 00 parts by weight at -50°C, which is a temperature that does not cause agglomeration, it was mixed with 15 parts by weight of stearyl alcohol using a stirrer with a cutter at a stirring speed of 20,000 rpm for a stirring time of 5.
The mixture was mixed and stirred for several minutes to obtain microcapsules. The temperature at the end of stirring was -30°C. Hydrophobic silica fine powder (product name Aerosil R972) 2 is added to this microcapsule.
Parts by weight were added and stirred at 20,000 rpm for 15 seconds at -10°C or lower. As a result, the yield of starch syrup microcapsules with a stearyl alcohol silica fine powder mixed wall that remains smooth even at room temperature and has excellent fluidity is 10%.
Obtained at 0%.
以上説明したように、この発明のマイクロカプセルの製
造法は、粉状とした場合に常温付近では液体となるかあ
るいは集塊化を起し、粉状を維持できない物質よりなる
芯物質を、その粉末が融解または集塊化を起すことのな
い低温度で連結粉砕し、ついでこの温度において上記芯
物質を壁物質もしくはこの壁物質と微粉末とともに混合
撹拌するものであるので、常温付近で液体または粘着性
を有する物質もしくは軟質物質あるいは水や有機溶剤に
侵されるかもしくはこれらと反応する物質を芯物質とす
ることができ、これら芯物質を極めて簡単な工程操作で
、短時間に、収率１００％でマイクロカプセルとするこ
とができ、粘着剤、接着剤、塗料をはじめとしてトナー
などの電子写真材料、医薬品、食品等に利用でき応用範
囲が非常に広範囲となる。また、従来法に比べて、製造
に際し、水や有機溶剤を全く使用しないので乾燥工程や
排液処理が不要となり、作業安全性も高い。As explained above, the method for producing microcapsules of the present invention is to remove the core material, which is made of a material that becomes liquid or agglomerates at room temperature when powdered, and cannot maintain its powdery state. The powder is connected and pulverized at a low temperature that does not cause melting or agglomeration, and then the core material is mixed and stirred with the wall material or the wall material and the fine powder at this temperature. A sticky substance, a soft substance, or a substance that is eroded by or reacts with water or an organic solvent can be used as a core substance, and these core substances can be processed in a very simple process, in a short time, and with a yield of 100%. % can be made into microcapsules, and can be used in adhesives, adhesives, paints, electrophotographic materials such as toner, medicines, foods, etc., and has a very wide range of applications. Furthermore, compared to conventional methods, since no water or organic solvents are used during production, there is no need for a drying process or wastewater treatment, resulting in higher work safety.
さらに、任意の粒径のマイクロカプセルを容易に製造す
ることができ、目的に応じた多様性に富むマイクロカプ
セルを製造できるなどの利点を有する。Further, it has the advantage that microcapsules of any particle size can be easily produced, and microcapsules with a wide variety of purposes can be produced.
Claims (2)
いは集塊化をおこし粉末が融解または集塊化をおこすこ
とのない低温度で凍結粉砕し、ついでこの温度において
上記芯物質を壁物質とともに混合撹拌して、芯物質を壁
物質で被覆するようにしたことを特徴とするマイクロカ
プセルの製造法。(1) When powdered, it becomes liquid or agglomerates at around room temperature, and the powder is freeze-pulverized at a low temperature that will not melt or agglomerate, and then the core material is separated into walls at this temperature. A method for producing microcapsules, characterized in that the core material is covered with a wall material by mixing and stirring with a substance.
いは集塊化をおこし粉状を維持できない物質よりなる芯
物質を、その粉末が融解または集塊化をおこすことのな
い低温度で凍結粉砕し、ついでこの温度で上記芯物質を
壁物質および微粉末とともに混合撹拌して、芯物質を壁
物質および微粉末で被覆するようにしたことを特徴とす
るマイクロカプセルの製造法。(2) The core material, which is made of a material that becomes liquid or agglomerates at room temperature and cannot maintain its powder form, is heated at a low temperature that does not cause the powder to melt or agglomerate. A method for producing microcapsules, which comprises freezing and pulverizing the core material, and then mixing and stirring the core material with the wall material and the fine powder at this temperature so that the core material is covered with the wall material and the fine powder.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57155538A JPS5946124A (en) | 1982-09-07 | 1982-09-07 | Preparation of microcapsule |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57155538A JPS5946124A (en) | 1982-09-07 | 1982-09-07 | Preparation of microcapsule |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5946124A true JPS5946124A (en) | 1984-03-15 |
| JPH0367736B2 JPH0367736B2 (en) | 1991-10-24 |
Family
ID=15608248
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57155538A Granted JPS5946124A (en) | 1982-09-07 | 1982-09-07 | Preparation of microcapsule |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5946124A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61242635A (en) * | 1985-04-18 | 1986-10-28 | Nippon Sanso Kk | Composition retarded in reactivity or dissolubility with water or acid and alkali aqueous solution and its production |
| JPS61242634A (en) * | 1985-04-18 | 1986-10-28 | Nippon Sanso Kk | Composition retarded in reactivity and dissolubility with water or acid and alkali aqueous solution and its production |
| JPH02164439A (en) * | 1988-12-15 | 1990-06-25 | Matsumoto Yushi Seiyaku Co Ltd | Microcapsule and its preparation method |
| JPH02164440A (en) * | 1988-12-15 | 1990-06-25 | Matsumoto Yushi Seiyaku Co Ltd | Microcapsule containing water-refusing component |
| WO2001013864A1 (en) * | 1999-08-24 | 2001-03-01 | Kose Corporation | Water-containing powder composition, process for producing the same, and cosmetic preparation containing the powder composition |
| JP2005232162A (en) * | 2004-01-23 | 2005-09-02 | Kose Corp | Powder composition and powdery cosmetic containing the same |
| JP2006225299A (en) * | 2005-02-16 | 2006-08-31 | Nagisa Kawagoe | Cosmetic |
| WO2013190240A1 (en) * | 2012-06-21 | 2013-12-27 | Centre National De La Recherche Scientifique | Multi-compartment material for the thermally stimulated delivery of substances of interest, preparation method thereof and uses of same |
| FR2992232A1 (en) * | 2012-06-21 | 2013-12-27 | Centre Nat Rech Scient | MULTICOMPARTIMENT MATERIAL FOR THE THERMOSTIMULATED DELIVERY OF INTEREST SUBSTANCES, PROCESS FOR PREPARATION,. |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS535694A (en) * | 1976-07-03 | 1978-01-19 | Kiyuugo Tanaka | Platinum wire used in combustible gas concentration measurements |
| JPS54104487A (en) * | 1978-02-04 | 1979-08-16 | Pentel Kk | Microcapsules and production thereof |
| JPS57155539A (en) * | 1981-03-23 | 1982-09-25 | Hitachi Ltd | Mask |
-
1982
- 1982-09-07 JP JP57155538A patent/JPS5946124A/en active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS535694A (en) * | 1976-07-03 | 1978-01-19 | Kiyuugo Tanaka | Platinum wire used in combustible gas concentration measurements |
| JPS54104487A (en) * | 1978-02-04 | 1979-08-16 | Pentel Kk | Microcapsules and production thereof |
| JPS57155539A (en) * | 1981-03-23 | 1982-09-25 | Hitachi Ltd | Mask |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61242634A (en) * | 1985-04-18 | 1986-10-28 | Nippon Sanso Kk | Composition retarded in reactivity and dissolubility with water or acid and alkali aqueous solution and its production |
| JPS61242635A (en) * | 1985-04-18 | 1986-10-28 | Nippon Sanso Kk | Composition retarded in reactivity or dissolubility with water or acid and alkali aqueous solution and its production |
| JPH02164439A (en) * | 1988-12-15 | 1990-06-25 | Matsumoto Yushi Seiyaku Co Ltd | Microcapsule and its preparation method |
| JPH02164440A (en) * | 1988-12-15 | 1990-06-25 | Matsumoto Yushi Seiyaku Co Ltd | Microcapsule containing water-refusing component |
| JP4514902B2 (en) * | 1999-08-24 | 2010-07-28 | 株式会社コーセー | Water-containing powder composition, process for producing the same, and cosmetics containing the powder composition |
| WO2001013864A1 (en) * | 1999-08-24 | 2001-03-01 | Kose Corporation | Water-containing powder composition, process for producing the same, and cosmetic preparation containing the powder composition |
| JP2001131528A (en) * | 1999-08-24 | 2001-05-15 | Kose Corp | Hydrous powder composition and method for producing the same and cosmetic containing the same |
| JP2005232162A (en) * | 2004-01-23 | 2005-09-02 | Kose Corp | Powder composition and powdery cosmetic containing the same |
| JP2006225299A (en) * | 2005-02-16 | 2006-08-31 | Nagisa Kawagoe | Cosmetic |
| WO2013190240A1 (en) * | 2012-06-21 | 2013-12-27 | Centre National De La Recherche Scientifique | Multi-compartment material for the thermally stimulated delivery of substances of interest, preparation method thereof and uses of same |
| FR2992232A1 (en) * | 2012-06-21 | 2013-12-27 | Centre Nat Rech Scient | MULTICOMPARTIMENT MATERIAL FOR THE THERMOSTIMULATED DELIVERY OF INTEREST SUBSTANCES, PROCESS FOR PREPARATION,. |
| FR2992231A1 (en) * | 2012-06-21 | 2013-12-27 | Centre Nat Rech Scient | MULTICOMPARTIMENT MATERIAL FOR THE THERMOSTIMULATED DELIVERY OF INTEREST SUBSTANCES, PROCESS FOR PREPARATION,. |
| WO2013190241A3 (en) * | 2012-06-21 | 2014-07-03 | Centre National De La Recherche Scientifique | Multi-compartment material for the thermally stimulated delivery of substances of interest, preparation method thereof and uses of same |
| JP2015523357A (en) * | 2012-06-21 | 2015-08-13 | サントレ ナティオナル ド ラ ルシェルシェ シアンティフィク | Multi-component materials, preparation processes and applications for thermally stimulated release of target substances |
| JP2015528794A (en) * | 2012-06-21 | 2015-10-01 | サントレ ナティオナル ド ラ ルシェルシェ シアンティフィク | Multi-component materials, preparation processes and applications for thermally stimulated release of target substances |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0367736B2 (en) | 1991-10-24 |
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