JPH0360730A - Suspensible microcapsule formulation - Google Patents
Suspensible microcapsule formulationInfo
- Publication number
- JPH0360730A JPH0360730A JP19249889A JP19249889A JPH0360730A JP H0360730 A JPH0360730 A JP H0360730A JP 19249889 A JP19249889 A JP 19249889A JP 19249889 A JP19249889 A JP 19249889A JP H0360730 A JPH0360730 A JP H0360730A
- Authority
- JP
- Japan
- Prior art keywords
- water
- mixture
- glycerin
- phase
- acetate
- 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 28
- 239000000203 mixture Substances 0.000 title claims abstract description 28
- 238000009472 formulation Methods 0.000 title description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 235000011187 glycerol Nutrition 0.000 claims abstract description 18
- 239000012528 membrane Substances 0.000 claims abstract description 18
- 239000011162 core material Substances 0.000 claims abstract description 15
- 239000000463 material Substances 0.000 claims abstract description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims abstract description 12
- 239000002775 capsule Substances 0.000 claims abstract description 7
- 238000012695 Interfacial polymerization Methods 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 7
- 239000000725 suspension Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 abstract description 5
- 102000004190 Enzymes Human genes 0.000 abstract description 3
- 108090000790 Enzymes Proteins 0.000 abstract description 3
- 239000003905 agrochemical Substances 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 3
- 239000000853 adhesive Substances 0.000 abstract description 2
- 230000001070 adhesive effect Effects 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 239000002537 cosmetic Substances 0.000 abstract description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 abstract description 2
- 230000003449 preventive effect Effects 0.000 abstract description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 2
- 238000005191 phase separation Methods 0.000 abstract 2
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 239000002304 perfume Substances 0.000 abstract 1
- -1 glometrin Chemical compound 0.000 description 15
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 230000002209 hydrophobic effect Effects 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000230 xanthan gum Substances 0.000 description 3
- 235000010493 xanthan gum Nutrition 0.000 description 3
- 229920001285 xanthan gum Polymers 0.000 description 3
- 229940082509 xanthan gum Drugs 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- KMZHZAAOEWVPSE-UHFFFAOYSA-N 2,3-dihydroxypropyl acetate Chemical compound CC(=O)OCC(O)CO KMZHZAAOEWVPSE-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OEYOMNZEMCPTKN-UHFFFAOYSA-N Butamifos Chemical compound CCC(C)NP(=S)(OCC)OC1=CC(C)=CC=C1[N+]([O-])=O OEYOMNZEMCPTKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000646892 Emberiza hortulana Species 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- UXDDRFCJKNROTO-UHFFFAOYSA-N Glycerol 1,2-diacetate Chemical compound CC(=O)OCC(CO)OC(C)=O UXDDRFCJKNROTO-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 101150007144 Intu gene Proteins 0.000 description 1
- 229920000161 Locust bean gum Polymers 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- CGTWCAVZZBLHQH-UHFFFAOYSA-N [cyano-(3-phenoxyphenyl)methyl] 2,2-dichloro-1-(4-ethoxyphenyl)cyclopropane-1-carboxylate Chemical compound C1=CC(OCC)=CC=C1C1(C(=O)OC(C#N)C=2C=C(OC=3C=CC=CC=3)C=CC=2)C(Cl)(Cl)C1 CGTWCAVZZBLHQH-UHFFFAOYSA-N 0.000 description 1
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- RQVYBGPQFYCBGX-UHFFFAOYSA-N ametryn Chemical compound CCNC1=NC(NC(C)C)=NC(SC)=N1 RQVYBGPQFYCBGX-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- DDHPBAGICYAAKM-UHFFFAOYSA-N decanedioic acid;dihydrochloride Chemical compound Cl.Cl.OC(=O)CCCCCCCCC(O)=O DDHPBAGICYAAKM-UHFFFAOYSA-N 0.000 description 1
- WMPOZLHMGVKUEJ-UHFFFAOYSA-N decanedioyl dichloride Chemical compound ClC(=O)CCCCCCCCC(Cl)=O WMPOZLHMGVKUEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 1
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 229950007035 homocamfin Drugs 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 235000010420 locust bean gum Nutrition 0.000 description 1
- 239000000711 locust bean gum Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- HGEVGSTXQGZPCL-UHFFFAOYSA-N nonanedioyl dichloride Chemical compound ClC(=O)CCCCCCCC(Cl)=O HGEVGSTXQGZPCL-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920005597 polymer membrane Polymers 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Fats And Perfumes (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Manufacturing Of Micro-Capsules (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は、マイクロカプセル製剤とその製造法に関する
。本発明のマイクロカプセル製剤はの分野で用いられる
。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a microcapsule formulation and a method for producing the same. The microcapsule formulation of the present invention is used in the field of.
〈従来の技術〉
マイクロカプセルの製剤とその製造法に関しては種々の
方法が検討されているが、芯物質の多くのものは、密度
が１．０（２０℃）以上であり、これらの芯物質を水中
で界面重合法又は、Ｉｎ −５ｉｔｕ重合法によりマイ
クロカプセル化し、懸濁状製剤にすると保存状態で層分
離し易い。<Prior art> Various methods have been studied regarding the preparation of microcapsules and their manufacturing methods, but many of the core materials have a density of 1.0 (at 20°C) or higher; If it is microencapsulated in water by an interfacial polymerization method or an in-5 intu polymerization method to form a suspension preparation, it is easy to separate the layers during storage.
懸濁製剤中の層分離に関しては水溶性増粘剤の添加ある
いは、軽比重溶剤を用いる方法（特開昭６４−２２８０
６）々どがある。Regarding layer separation in suspension preparations, the method of adding a water-soluble thickener or using a light specific gravity solvent (Japanese Patent Application Laid-Open No. 64-2280
6) There are many.
〈発明が解決しようとする課題〉
懸濁製剤は、連続相と不連続相の密度の違いから、保存
中の層分離が問題となっている。それらを解決するため
の連続相の粘度を高くする方法がしばしば用いられるが
、取扱いの面で問題がある。また、不連続相に軽比重溶
剤を用いる方法は、薬剤及びカプセル膜へ影響をあたえ
る場合があり、使用が限定される。<Problems to be Solved by the Invention> Suspension preparations have a problem of layer separation during storage due to the difference in density between the continuous phase and the discontinuous phase. To solve these problems, a method of increasing the viscosity of the continuous phase is often used, but there are problems in handling. Furthermore, the method of using a low specific gravity solvent in the discontinuous phase may have an effect on the drug and the capsule membrane, which limits its use.
また従来の懸濁製剤は、容器の内側特に蓋の部分に付着
した組成物が水分の蒸散とともに固化し、開栓しにくく
なったり、難分散性になったりする場合がある。In addition, with conventional suspension preparations, the composition adhering to the inside of the container, particularly the lid, solidifies as water evaporates, making it difficult to open or dispersible.
く課題を解決するための手段〉
これらの課題を解決するために本発明者らは鋭意検討し
た結果、本発明に達した。すなわち本発明は芯物質が水
とグリセリン若しくはそのアセテートの混合液に難溶性
のカプセル膜に包含され、水とグリセリン若しくはその
アセテートの混合液を連続相とし、これに不連続相とし
てマイクロカプセルを懸濁したことを特徴とする懸濁状
マイクロカプセル製剤にＩＭｆる。Means for Solving the Problems> In order to solve these problems, the present inventors conducted extensive studies and arrived at the present invention. That is, in the present invention, the core substance is included in a capsule membrane that is poorly soluble in a mixture of water and glycerin or its acetate, the mixture of water and glycerin or its acetate is used as a continuous phase, and microcapsules are suspended in this as a discontinuous phase. IMf is applied to suspended microcapsule formulations characterized by cloudiness.
以下本発明の詳細な説明する。The present invention will be explained in detail below.
本発明のマイクロカプセル製剤の芯物質としては、例え
ば各種抗生物質、合成品、アミノ酸などの医薬、殺虫剤
、除草剤、殺菌剤などの農薬、顔料、分散染料、ロイコ
染料、感熱又は感圧染料などの色素メンンールエッセン
スなの香料、ポリサルファイド、エポキシ樹脂などの接
着剤、ビフェニル系、フェニルシクロヘキサン系などの
液晶物質、合成、酵素系洗剤、ベンゼン、エステル、パ
ラフィンなどの溶剤、硬化剤、開始剤などの触媒、その
他各種の酵素、化粧品又は防錆剤々とをあげることがで
きる。特に下記にあげる農薬を芯物質に使用した場合、
優れた効果が期待できる。例えば殺虫剤としては、ダイ
アノジン、カヤフォス、ダイジストン、マラソン、ガー
ドサイド、バイジット、カルホス、オルトラン、スミチ
オン、バッサ、シクロサール等、除草剤としては、ＭＣ
ＰＢ 、ブタクロール、グロメトリン、プロパジン、シ
メトリン、アメトリン、ブタミホス、オキサシアシン等
、殺菌剤としては、ＩＢＰ、プロロベナゾール、インブ
ロチオラン、トリジクラゾール等であるが、かならずし
もこれらの農薬に限られるものではない。これらの農薬
の一種単独、または二種以上混合して使用することもで
きる。The core substances of the microcapsule formulation of the present invention include, for example, various antibiotics, synthetic products, medicines such as amino acids, agricultural chemicals such as insecticides, herbicides, and fungicides, pigments, disperse dyes, leuco dyes, heat-sensitive or pressure-sensitive dyes. Pigments such as menhol essence, fragrances, adhesives such as polysulfide and epoxy resin, liquid crystal substances such as biphenyl and phenylcyclohexane, synthetic and enzyme detergents, solvents such as benzene, esters and paraffin, curing agents, and initiators. Examples include catalysts such as, various other enzymes, cosmetics, and rust preventives. In particular, when the pesticides listed below are used as core materials,
Excellent effects can be expected. For example, insecticides include Dianodine, Kayafos, Digeston, Marathon, Guardside, Visit, Calphos, Ortolan, Sumithion, Bassa, Cyclosal, etc., and herbicides include MC.
PB, butachlor, glometrin, propazine, cymetrine, ametrine, butamifos, oxacyacin, etc., and the fungicides include IBP, prorobenazole, imbrothiolane, tridiclazole, etc., but are not necessarily limited to these pesticides. These agricultural chemicals can be used alone or in combination.
次に本発明のマイクロカプセル製剤の膜材は水とグリセ
リン若しくはそのアセテートの混合液に難溶性であるこ
とを必須の要件とするものである。このような膜材の原
料としては例えば以下のものをあげることができる。Next, it is an essential requirement that the membrane material of the microcapsule formulation of the present invention be sparingly soluble in a mixture of water and glycerin or its acetate. Examples of raw materials for such membrane materials include the following.
油溶性膜材としては、多価イノシアネート、多価カルボ
ン酸クロライド、多価スルホン酸クロライド等、例えば
ヘキサメチレンジイソシアネート、トリメチルへキサメ
チレンジイソシアネート、インホロンジイソシアネート
、フェニレンジイソシアネート、トルエンジイソシアネ
ート、キシリレンジイソシアネート、ナフタレンジイソ
シアネート、ポリメチレンポリフェニルイソシアネート
、セバシン酸ジクロライド、アジピン酸ジクロライド、
アゼライン酸ジクロライド、テレフタル酸ジクロライド
、トリメシン酸シクロライド、ベンゼンスルホニルシク
ロライド等、一方、水溶性膜材としては、多価アミン、
多価ヒドロキシ化合物等、例えばエチレンジアミン、ヘ
キサメチレンジアミン、フェニレンジアミン、ジエチレ
ントリアミン、トリエチレンテトラミン、ピペラジン、
エチレングリコール、フタンジオール、ヘキサンジオー
ル、ポリエチレングリコール等がある。Examples of oil-soluble membrane materials include polyvalent inocyanate, polyvalent carboxylic acid chloride, polyvalent sulfonic acid chloride, etc., such as hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, inphorone diisocyanate, phenylene diisocyanate, toluene diisocyanate, xylylene diisocyanate, naphthalene diisocyanate, polymethylene polyphenylisocyanate, sebacic acid dichloride, adipic acid dichloride,
Azelaic acid dichloride, terephthalic acid dichloride, trimesic acid cyclolide, benzenesulfonyl cyclolide, etc. On the other hand, water-soluble membrane materials include polyvalent amines,
Polyvalent hydroxy compounds, such as ethylenediamine, hexamethylenediamine, phenylenediamine, diethylenetriamine, triethylenetetramine, piperazine,
Examples include ethylene glycol, phthanediol, hexanediol, and polyethylene glycol.
次に本発明の懸濁状マイクロカプセル製剤の製造法を説
明する。Next, a method for manufacturing the suspended microcapsule formulation of the present invention will be explained.
Ｉｎ −５ｉｔｕ重合法によるマイクロカプセル化方法
は、疎水性物質を水とグリセリン若しくはそのアセテー
トの混合液に分散させた状態で液滴界面で両液体に不溶
性性の高分子膜を形成させる点では後記の界面重合法と
似ているが、膜材を芯物質の内側からあるいは外側から
のいずれか一方だけから供給する点で異ねっている。こ
の方法の分散及び反応の工程は後記の界面重合法と同一
条件が適用されうるが、膜材としては芯物質内部からの
形成では、アクリル酸エステル、メタクリル酸エステル
、酢酸ビニル、スチレン、ジビニルベンゼン、エチレン
ジメタクリレート等、ラジカル重合によるものを用いる
のが好ましい。また芯物質外部からの形成では、尿素／
ホルマリン、メラミン／ホルマリン、フェノール／ホル
マリン等の重付加反応によるものを用いるのが好ましい
。これらの膜材の種類（単独または組合せの混合物）及
び使用量は、芯物質の種類、また、マイクロカプセルの
使用目的によって異なり、効果が発揮される範囲で選択
される。The microencapsulation method using the In-5 itu polymerization method is described later in that a hydrophobic substance is dispersed in a mixture of water and glycerin or its acetate, and a polymer film insoluble in both liquids is formed at the droplet interface. This method is similar to the interfacial polymerization method described above, but differs in that the membrane material is supplied either from the inside or the outside of the core material. The same conditions as for the interfacial polymerization method described later can be applied to the dispersion and reaction steps of this method, but when forming the film from inside the core material, acrylic ester, methacrylic ester, vinyl acetate, styrene, divinylbenzene, etc. , ethylene dimethacrylate, etc., which are produced by radical polymerization, are preferably used. In addition, in the case of formation from outside the core material, urea/
It is preferable to use formalin, melamine/formalin, phenol/formalin, etc. by polyaddition reaction. The type and amount of these membrane materials used (individually or as a mixture) vary depending on the type of core substance and the intended use of the microcapsules, and are selected within a range that provides the desired effect.
次に、本発明の界面重合法によるマイクロカプセル化方
法は例えば次のようにして行なう。Next, the microencapsulation method using the interfacial polymerization method of the present invention is carried out, for example, as follows.
即ち、疎水性芯物質と油溶性膜材との混合物を所定の撹
拌条件で、水溶性分散剤及び／又は乳化剤（目的とする
カプセル粒子の平均粒径及び粒度分布によって選択する
）を溶解した水とグリセリン若しくはそのアセテートの
混合液中に分散させ所望する粒径の分散体を得る。この
系に水溶性膜材の水溶液を撹拌しつつ滴下し、液滴界面
で油溶性膜材と水溶性膜材を反応させ両液体に不溶性高
分子膜を形成せしめて疎水性芯物質を内包するこの時の
反応温度は、膜材また疎水性芯物質の種類、組合せに′
よって設定されるが３０〜８０℃の間で行たわれるのが
好ましい。ここで用いられる水溶性分散剤としては、ア
ラビアガム、アルギン酸ソーダ、ローカストビーンガム
、ザンタンサンガム等の天然多糖類、カルボキシメチル
セルロース、メチルセルロース等の半合成多糖類、ポリ
ビニルアルコール等の合成高分子等を単独または二種以
上用いる、その時の添加量は全組成物に対して０．０１
％〜１Ｏ１０％好ましくは０．１％〜３．０％である。That is, a mixture of a hydrophobic core material and an oil-soluble film material is stirred under predetermined stirring conditions, and a water-soluble dispersant and/or emulsifier (selected depending on the average particle size and particle size distribution of the target capsule particles) is dissolved in water. and glycerin or its acetate to obtain a dispersion having a desired particle size. An aqueous solution of a water-soluble membrane material is dropped into this system while stirring, and the oil-soluble membrane material and water-soluble membrane material react at the droplet interface, forming an insoluble polymer membrane in both liquids and encapsulating the hydrophobic core substance. The reaction temperature at this time depends on the type and combination of membrane materials and hydrophobic core materials.
Therefore, the temperature is preferably set between 30 and 80°C. The water-soluble dispersants used here include natural polysaccharides such as gum arabic, sodium alginate, locust bean gum, and xanthan gum, semi-synthetic polysaccharides such as carboxymethylcellulose and methylcellulose, and synthetic polymers such as polyvinyl alcohol. When used alone or in combination, the amount added is 0.01 to the total composition.
% to 10%, preferably 0.1% to 3.0%.
また、乳化剤としては、ポリオキシエチレンアルキルエ
ーテル、ポリオキシエチレンアルキルフェニルエーテル
、アルキルフェニル縮合物エーテル、ポリオキシエチレ
ンアルキ克エステル。Examples of emulsifiers include polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, alkylphenyl condensate ether, and polyoxyethylene alkyl ester.
ポリオキシエチレンアルキルアミノエーテル、ポリオキ
シエチレンアルキルアミド、ポリオキシエチレンポリオ
キシプロピレンエーテル、ポリオキシエチレン植物油エ
ーテル、ソルビタンエステル、ポリオキシエチレンソル
ビタンエステル、ポリオキシエチレンアルキレンアリル
フェニルエーテル等の単独または二種以上を用いる。そ
の時の添加量は、０％〜１０．０％好ましくはＯ〜３．
０％である。Single or two or more of polyoxyethylene alkylamino ether, polyoxyethylene alkylamide, polyoxyethylene polyoxypropylene ether, polyoxyethylene vegetable oil ether, sorbitan ester, polyoxyethylene sorbitan ester, polyoxyethylene alkylene allyl phenyl ether, etc. Use. The amount added at that time is 0% to 10.0%, preferably O to 3.0%.
It is 0%.
々お、本発明の製剤を製造するに当っては、マイクロカ
プセル化は水のみを連続相として用い、マイクロカプセ
ル化が終了してからグリセリン若しくはそのアセテート
を加えてもよい。In producing the preparation of the present invention, microencapsulation may be carried out using only water as a continuous phase, and glycerin or its acetate may be added after microencapsulation is completed.
又、混合する溶剤はグリセリンのほかにグリセリンモノ
アセテート、グリセリンジアセテートがあげられる。In addition to glycerin, the solvent to be mixed may include glycerin monoacetate and glycerin diacetate.
一般のマイクロカプセル（不連続相）は、密度が１．０
ｇ／ｃｍ３以上であり、連続相が水だけの場合は、マイ
クロカプセルが容易に沈降し、容器の底で固結すること
があるが、本発明では、連続相を水とグリセリンの混合
液にしたため、その密度がマイクロカプセルの密度に近
づけるこれにより沈降の問題を解決することができた。General microcapsules (discontinuous phase) have a density of 1.0
g/cm3 or more and the continuous phase is only water, the microcapsules may easily settle and solidify at the bottom of the container, but in the present invention, the continuous phase is a mixture of water and glycerin. Therefore, its density approached that of microcapsules, which solved the problem of sedimentation.
すなわち不連続相の密度を１．０５〜１．２５ ｇ／ｃ
ｍ３、好ましくは１．０５〜１．２０ ｇ／ｃｍ３にし
、連続相と不連続相の密度比を１．０付近好ましくは０
．９５〜１．０５にすることにより発明の目的を達成す
ることができた。That is, the density of the discontinuous phase is 1.05 to 1.25 g/c.
m3, preferably 1.05 to 1.20 g/cm3, and the density ratio of the continuous phase to the discontinuous phase is around 1.0, preferably 0.
．． The purpose of the invention could be achieved by setting the ratio to 95 to 1.05.
〈発明の効果〉
本発明のマイクロカプセル製剤は、マイクロカプセルの
層分離が認められず、製剤の粘度も適当で極めて使用し
やすい。<Effects of the Invention> In the microcapsule preparation of the present invention, no layer separation of the microcapsules is observed, the viscosity of the preparation is appropriate, and it is extremely easy to use.
〈実施例〉 以下実施例により本発明を説明する。<Example> The present invention will be explained below with reference to Examples.
実施例１゜
撹拌装置をそなえた１沼のガラス反応釜に、水溶性分散
剤ゴーセノールＧＨ−１７（日本合成社製）５ｇ１キサ
ンタンガム０．５ｇ、乳化剤ニューカルゲンＤ４１０（
折本油脂社製）０．５ｇをとり、水１３４ｇ及びグリセ
リン１７５ｇに溶解する。これに、ミリオネートＭＲ−
４００（日本ポリウレタン社製）１０ｇとダイアジノン
１２５ｇの混合液を加えて、回転数６５ Ｏｒｐｍで１
０分間撹拌し、分散体を作る。次に撹拌を２５０ ｒｐ
ｍに下げて、エチレンジアミン、ジエチレントリアミン
各２ｇに水を加えて５０ｇにした溶液を室温で徐々に滴
下する。滴下後液温を６０℃に上げて反応を完結させる
。反応終了後、３０℃に液温を下げ、１８％の塩酸で中
和し、懸濁状のマイクロカプセル製剤を得る。Example 1 Into a 1-sized glass reaction pot equipped with a stirring device, 5 g of water-soluble dispersant Gohsenol GH-17 (manufactured by Nippon Gosei Co., Ltd.), 0.5 g of xanthan gum, and emulsifier Nucalgen D410 (
Take 0.5 g (manufactured by Orimoto Yushi Co., Ltd.) and dissolve it in 134 g of water and 175 g of glycerin. In addition to this, Millionate MR-
Add a mixture of 10 g of 400 (manufactured by Nippon Polyurethane Co., Ltd.) and 125 g of diazinon, and rotate at 65 orpm.
Stir for 0 minutes to form a dispersion. Then stir at 250 rp.
m, and a solution of 2 g each of ethylenediamine and diethylenetriamine added with water to make 50 g was gradually added dropwise at room temperature. After dropping, the temperature of the solution was raised to 60°C to complete the reaction. After the reaction is completed, the temperature of the solution is lowered to 30° C. and neutralized with 18% hydrochloric acid to obtain a suspended microcapsule preparation.
比較例−１
実施例１のグリセリンを全量水に置き換えて同様の方法
で懸濁状マイクロカプセル製剤を得る。Comparative Example-1 A suspended microcapsule preparation is obtained in the same manner as in Example 1 except that the glycerin is completely replaced with water.
試験−１、
実施例１及び比較例−１の製剤について容器内での層分
離について試験を実施した。Test-1, the formulations of Example 1 and Comparative Example-1 were tested for layer separation within the container.
（試験方法）
上記製剤１００ｇをＮ１１ｌｌのＪＩＳ瓶に入れ室温及
び４０°Ｃ±１℃の恒温槽に保存し、層分離状態を観察
した。(Test method) 100 g of the above preparation was placed in a N11 liter JIS bottle and stored in a constant temperature bath at room temperature and 40°C±1°C, and the state of layer separation was observed.
実施例２６
実施例１の装置を用い、水溶性分散剤としてアラビアガ
ム１０ｇ１キサンタンガム０．５ｇ、乳化剤として二一
一カルゲンＤ−２１２（溺水油脂社製）０．５ｇをとり
、水９４ｇ及びグリセリン２１０ｇに溶解する。これに
コロネート３０５３（日本ポリウレタン社製） ５ ｇ
、セバシン酸ジクロライド５ｇ及びグイジストン１２５
ｇの混合液を加えて実施例１と同様の操作で分散体を作
る。次にエチレンジアミン、ジエチレントリアミン、カ
性ソーダ各２ｇに水を加えて５０ｇにした溶液を滴下し
、実施例１と同様の操作で懸濁状マイクロカプセル製剤
を得る。Example 26 Using the apparatus of Example 1, take 10 g of gum arabic, 0.5 g of xanthan gum as a water-soluble dispersant, 0.5 g of 211 Kalgen D-212 (manufactured by Dosui Yushi Co., Ltd.) as an emulsifier, and add 94 g of water and 210 g of glycerin. dissolve in Add to this 5 g of Coronate 3053 (manufactured by Nippon Polyurethane Co., Ltd.)
, sebacate dichloride 5g and Guidistone 125
A dispersion is prepared in the same manner as in Example 1 by adding the mixture of g. Next, a solution made by adding water to 2 g each of ethylenediamine, diethylenetriamine, and caustic soda to make 50 g was added dropwise, and the same procedure as in Example 1 was carried out to obtain a suspended microcapsule preparation.
比較例−２
実施例２のグリセリンを全量水に置き換えて同様の方法
で懸濁状マイクロカプセル製剤を得る。Comparative Example 2 A suspended microcapsule preparation is obtained in the same manner as in Example 2, except that the entire amount of glycerin is replaced with water.
試験−２゜
試験へ−１と同様の方法で実施例２及び比較例＝２の製
剤について容器内での層分離について試験を実施した。Test-2゜To Test-1 A test was conducted on the formulations of Example 2 and Comparative Example 2 for layer separation in the container in the same manner as in Test-1.
Claims (1)
混合液に難溶性のカプセル膜に包含され、水とグリセリ
ン若しくはそのアセテートの混合液を連続相とし、これ
に不連続相としてマイクロカプセルを懸濁したことを特
徴とする懸濁状マイクロカプセル製剤。 ２、不連続相の密度が１．０〜１．２５ｇ／ｃｍ＾３で
ある特許請求の範囲１の懸濁状マイクロカプセル製剤。 ３、連続相と不連続相の密度の比が０．９５〜１．０５
である特許請求の範囲１の懸濁状マイクロカプセル製剤
。 ４、芯物質及びカプセル膜材を水とグリセリン若しくは
そのアセテートの混合液に分散させ界面重合法又は、Ｉ
ｎ−ｓｉｔｕ重合法によりマイクロカプセル化すること
を特徴とする懸濁状マイクロカプセル製剤の製造法。[Scope of Claims] 1. The core substance is contained in a capsule membrane that is poorly soluble in a mixture of water and glycerin or its acetate, and the mixture of water and glycerin or its acetate is used as a continuous phase, and the mixture of water and glycerin or its acetate is used as a discontinuous phase. A suspended microcapsule preparation characterized by suspending microcapsules. 2. The suspended microcapsule preparation according to claim 1, wherein the density of the discontinuous phase is 1.0 to 1.25 g/cm^3. 3. The ratio of the density of the continuous phase to the discontinuous phase is 0.95 to 1.05
The suspension microcapsule preparation according to claim 1. 4. Interfacial polymerization method in which the core material and capsule membrane material are dispersed in a mixture of water and glycerin or its acetate
1. A method for producing a suspended microcapsule preparation, which is characterized by microencapsulation using an n-situ polymerization method.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19249889A JP2962740B2 (en) | 1989-07-27 | 1989-07-27 | Suspended microcapsule formulation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19249889A JP2962740B2 (en) | 1989-07-27 | 1989-07-27 | Suspended microcapsule formulation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0360730A true JPH0360730A (en) | 1991-03-15 |
| JP2962740B2 JP2962740B2 (en) | 1999-10-12 |
Family
ID=16292308
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19249889A Expired - Fee Related JP2962740B2 (en) | 1989-07-27 | 1989-07-27 | Suspended microcapsule formulation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2962740B2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005238118A (en) * | 2004-02-26 | 2005-09-08 | Tosoh Corp | Method and apparatus for producing solidified particles using microchannel structure |
| JP2012006872A (en) * | 2010-06-25 | 2012-01-12 | Sansho Pharmaceutical Co Ltd | Oil-dispersed type composition in water/oil |
| DE102010040009A1 (en) * | 2010-08-31 | 2012-03-01 | Bizerba Gmbh & Co. Kg | labeling |
| EP2204156B1 (en) | 2008-12-30 | 2017-02-01 | Takasago International Corporation | Fragrance composition for core shell microcapsules |
| WO2021023647A1 (en) * | 2019-08-05 | 2021-02-11 | Firmenich Sa | Poly(amide-ester) microcapsules |
-
1989
- 1989-07-27 JP JP19249889A patent/JP2962740B2/en not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005238118A (en) * | 2004-02-26 | 2005-09-08 | Tosoh Corp | Method and apparatus for producing solidified particles using microchannel structure |
| EP2204156B1 (en) | 2008-12-30 | 2017-02-01 | Takasago International Corporation | Fragrance composition for core shell microcapsules |
| JP2012006872A (en) * | 2010-06-25 | 2012-01-12 | Sansho Pharmaceutical Co Ltd | Oil-dispersed type composition in water/oil |
| DE102010040009A1 (en) * | 2010-08-31 | 2012-03-01 | Bizerba Gmbh & Co. Kg | labeling |
| WO2021023647A1 (en) * | 2019-08-05 | 2021-02-11 | Firmenich Sa | Poly(amide-ester) microcapsules |
| CN113557081A (en) * | 2019-08-05 | 2021-10-26 | 弗门尼舍有限公司 | Poly(amide-ester) microcapsules |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2962740B2 (en) | 1999-10-12 |
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