JPH0283031A - Preparation of microcapsule - Google Patents
Preparation of microcapsuleInfo
- Publication number
- JPH0283031A JPH0283031A JP63235390A JP23539088A JPH0283031A JP H0283031 A JPH0283031 A JP H0283031A JP 63235390 A JP63235390 A JP 63235390A JP 23539088 A JP23539088 A JP 23539088A JP H0283031 A JPH0283031 A JP H0283031A
- Authority
- JP
- Japan
- Prior art keywords
- oils
- fats
- microcapsules
- oil
- amino acids
- 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.)
- Pending
Links
- 239000003094 microcapsule Substances 0.000 title claims abstract description 40
- 150000001413 amino acids Chemical class 0.000 claims abstract description 42
- 239000003921 oil Substances 0.000 claims abstract description 38
- 239000003925 fat Substances 0.000 claims abstract description 35
- 239000000126 substance Substances 0.000 claims abstract description 35
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 33
- -1 alkylene glycol Chemical compound 0.000 claims abstract description 25
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000002002 slurry Substances 0.000 claims abstract description 12
- 108010016626 Dipeptides Proteins 0.000 claims abstract description 7
- 239000006185 dispersion Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 6
- 108090000765 processed proteins & peptides Proteins 0.000 abstract description 12
- 239000000463 material Substances 0.000 abstract description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract description 6
- 239000011248 coating agent Substances 0.000 abstract description 6
- 238000000576 coating method Methods 0.000 abstract description 6
- 238000004090 dissolution Methods 0.000 abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 4
- 125000003275 alpha amino acid group Chemical group 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- 229940024606 amino acid Drugs 0.000 description 39
- 235000001014 amino acid Nutrition 0.000 description 39
- 239000011162 core material Substances 0.000 description 35
- 235000019198 oils Nutrition 0.000 description 32
- 235000019197 fats Nutrition 0.000 description 29
- 238000005538 encapsulation Methods 0.000 description 22
- 239000012528 membrane Substances 0.000 description 9
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 9
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 9
- 235000015278 beef Nutrition 0.000 description 7
- 239000002775 capsule Substances 0.000 description 7
- 102000004196 processed proteins & peptides Human genes 0.000 description 7
- 239000003760 tallow Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- YMAWOPBAYDPSLA-UHFFFAOYSA-N glycylglycine Chemical compound [NH3+]CC(=O)NCC([O-])=O YMAWOPBAYDPSLA-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 2
- SCCPDJAQCXWPTF-VKHMYHEASA-N Gly-Asp Chemical compound NCC(=O)N[C@H](C(O)=O)CC(O)=O SCCPDJAQCXWPTF-VKHMYHEASA-N 0.000 description 2
- YIWFXZNIBQBFHR-LURJTMIESA-N Gly-His Chemical compound [NH3+]CC(=O)N[C@H](C([O-])=O)CC1=CN=CN1 YIWFXZNIBQBFHR-LURJTMIESA-N 0.000 description 2
- PAWIVEIWWYGBAM-YUMQZZPRSA-N Gly-Leu-Ala Chemical compound NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(O)=O PAWIVEIWWYGBAM-YUMQZZPRSA-N 0.000 description 2
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 2
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 2
- QVHMSMOUDQXMRS-UHFFFAOYSA-N PPG n4 Chemical compound CC(O)COC(C)COC(C)COC(C)CO QVHMSMOUDQXMRS-UHFFFAOYSA-N 0.000 description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 2
- 235000019658 bitter taste Nutrition 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 235000020776 essential amino acid Nutrition 0.000 description 2
- 239000003797 essential amino acid Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 108010020688 glycylhistidine Proteins 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 235000014593 oils and fats Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- BZJTUOGZUKFLQT-UHFFFAOYSA-N 1,3,5,7-tetramethylcyclooctane Chemical group CC1CC(C)CC(C)CC(C)C1 BZJTUOGZUKFLQT-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- QDGAVODICPCDMU-UHFFFAOYSA-N 2-amino-3-[3-[bis(2-chloroethyl)amino]phenyl]propanoic acid Chemical compound OC(=O)C(N)CC1=CC=CC(N(CCCl)CCCl)=C1 QDGAVODICPCDMU-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- MGHKSHCBDXNTHX-WDSKDSINSA-N Glu-Gln Chemical group OC(=O)CC[C@H](N)C(=O)N[C@@H](CCC(N)=O)C(O)=O MGHKSHCBDXNTHX-WDSKDSINSA-N 0.000 description 1
- IKAIKUBBJHFNBZ-LURJTMIESA-N Gly-Lys Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)CN IKAIKUBBJHFNBZ-LURJTMIESA-N 0.000 description 1
- 108010008488 Glycylglycine Proteins 0.000 description 1
- 150000008575 L-amino acids Chemical class 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
- 229930182844 L-isoleucine Natural products 0.000 description 1
- 239000004395 L-leucine Substances 0.000 description 1
- 235000019454 L-leucine Nutrition 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- LESXFEZIFXFIQR-LURJTMIESA-N Leu-Gly Chemical compound CC(C)C[C@H](N)C(=O)NCC(O)=O LESXFEZIFXFIQR-LURJTMIESA-N 0.000 description 1
- HGNRJCINZYHNOU-LURJTMIESA-N Lys-Gly Chemical compound NCCCC[C@H](N)C(=O)NCC(O)=O HGNRJCINZYHNOU-LURJTMIESA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- WOUIMBGNEUWXQG-VKHMYHEASA-N Ser-Gly Chemical compound OC[C@H](N)C(=O)NCC(O)=O WOUIMBGNEUWXQG-VKHMYHEASA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- CXISPYVYMQWFLE-UHFFFAOYSA-N alanylglycine Chemical compound CC(N)C(=O)NCC(O)=O CXISPYVYMQWFLE-UHFFFAOYSA-N 0.000 description 1
- 108010047495 alanylglycine Proteins 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229960001230 asparagine Drugs 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 102000038379 digestive enzymes Human genes 0.000 description 1
- 108091007734 digestive enzymes Proteins 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 108010039216 glycylaspartic acid Proteins 0.000 description 1
- 229940043257 glycylglycine Drugs 0.000 description 1
- 108010050848 glycylleucine Proteins 0.000 description 1
- 108010015792 glycyllysine Proteins 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960002885 histidine Drugs 0.000 description 1
- 239000008173 hydrogenated soybean oil Substances 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- 229960003136 leucine Drugs 0.000 description 1
- 235000021056 liquid food Nutrition 0.000 description 1
- 108010064235 lysylglycine Proteins 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000008935 nutritious Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- IFGCUJZIWBUILZ-UHFFFAOYSA-N sodium 2-[[2-[[hydroxy-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyphosphoryl]amino]-4-methylpentanoyl]amino]-3-(1H-indol-3-yl)propanoic acid Chemical compound [Na+].C=1NC2=CC=CC=C2C=1CC(C(O)=O)NC(=O)C(CC(C)C)NP(O)(=O)OC1OC(C)C(O)C(O)C1O IFGCUJZIWBUILZ-UHFFFAOYSA-N 0.000 description 1
- WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 229960002898 threonine Drugs 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 229960004295 valine Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 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
- B01J13/04—Making microcapsules or microballoons by physical processes, e.g. drying, spraying
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Grain Derivatives (AREA)
- Medicinal Preparation (AREA)
- Dispersion Chemistry (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Fats And Perfumes (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- General Preparation And Processing Of Foods (AREA)
- Jellies, Jams, And Syrups (AREA)
- Formation And Processing Of Food Products (AREA)
Abstract
Description
【発明の詳細な説明】 量泉上坐■几分立 本発明は、アミノ酸由来の苦味がほとんどなく。[Detailed description of the invention] Qizumi Jōza ■ 几 Bunri The present invention has almost no bitterness derived from amino acids.
食品、医薬品として好適に利用できるアミノ酸。Amino acids that can be suitably used as foods and medicines.
ジペプチド、トリペプチド又はそれらの塩を芯物質とし
て油脂で被覆したマイクロカプセルの製造方法に関する
。The present invention relates to a method for producing microcapsules in which dipeptides, tripeptides, or salts thereof are used as a core material and coated with oil or fat.
来の 術 び 明が しようとする課従来、アミノ酸
等を油脂で被覆してマイクロカプセルを得る方法は種々
知られている(特公昭39−5911号、同49−10
912号、同49−45224号公報)、。Various methods have been known to obtain microcapsules by coating amino acids, etc. with fats and oils (Japanese Patent Publication No. 39-5911, No. 49-10).
No. 912, No. 49-45224).
しかし、特公昭39−5911号公報記載の方法はカプ
セル化媒体として高価なシリコーン油、ふっ素化油状物
等を使用しているため、経済的に不利である上、これら
媒体にカプセル膜材の油脂がかなり溶解してしまうとい
う問題を有している。However, the method described in Japanese Patent Publication No. 39-5911 is economically disadvantageous because it uses expensive silicone oil, fluorinated oil, etc. as the encapsulation medium. The problem is that it dissolves considerably.
また、特公昭49−10912号公報には、水溶性アミ
ノ酸のカプセル化法が提案されているが。Furthermore, Japanese Patent Publication No. 10912/1983 proposes a method for encapsulating water-soluble amino acids.
この方法では難溶性のアミノ酸又は水溶性アミノ酸と難
溶性アミノ酸との混合物を芯物質とすると。In this method, a poorly soluble amino acid or a mixture of a water-soluble amino acid and a poorly soluble amino acid is used as the core material.
膜材による被覆が十分に行なわれず、カプセル化し難い
という欠点がある。There is a drawback that the coating with the membrane material is not sufficient and it is difficult to encapsulate it.
更に、特公昭49−45224号公報記載の含アミノ酸
油脂カプセルの製法は、カプセル化媒体として水を使用
し、かつ20〜40℃の温度条件下でカプセル化を行な
うため、水温が40℃を超えると芯物質であるアミノ酸
の媒体(水)中への溶出が大となり、しかも融点が40
℃以上の油脂のみを膜材として用いることができない。Furthermore, the method for manufacturing amino acid-containing oil and fat capsules described in Japanese Patent Publication No. 49-45224 uses water as the encapsulation medium and encapsulates at a temperature of 20 to 40°C, so the water temperature exceeds 40°C. The elution of the core substance amino acid into the medium (water) becomes large, and the melting point is 40%.
It is not possible to use only fats and oils with a temperature of ℃ or higher as a membrane material.
このように、従来の製造方法では、高品質で実用的なア
ミノ酸含有油脂マイクロカプセルを得ることは困難であ
った。As described above, it has been difficult to obtain high-quality and practical amino acid-containing fat and oil microcapsules using conventional production methods.
本発明は、上記事情に鑑みなされたもので、アミノ酸や
ペプチドを水溶性、難溶性を問わず、マイクロカプセル
化でき、膜材の油脂の溶解や芯物質の溶出がほとんどな
く、高品質でしかも実用性に優れたアミノ酸及び/又は
ペプチド含有油脂マイクロカプセルを製造することがで
きるマイクロカプセルの製造方法を提供することを目的
とする。The present invention was developed in view of the above circumstances, and allows amino acids and peptides to be microencapsulated, regardless of whether they are water-soluble or poorly soluble, with almost no dissolution of oil or fat in the membrane material or elution of core substances, and high quality. An object of the present invention is to provide a method for producing microcapsules that can produce highly practical amino acid and/or peptide-containing oil and fat microcapsules.
を するための び
本発明者は、上記目的を達成するため鋭意検討を重ねた
結果、アミノ酸、ジペプチド、トリペプチド及びそれら
の塩から選ばれる1種又は2種以上の芯物質を油脂で被
覆する際に、カプセル化媒体として上記芯物質や油脂を
殆んど溶解させることのない分子量60〜400のアル
キレングルコールを使用し、上記芯物質を好ましくは4
0〜100℃に加温した油脂中に分散した後、この芯物
質分散スラリーを好ましくは40〜100℃に加温した
上記分子量のアルキレングルコール中に添加9分散する
ことにより、急激な冷却下でアルキレングルコール中に
おいてアミノ酸との親和性が高い油脂が上記芯物質表面
に被覆性に優れた被膜を形成し、それ故、膜材(油脂)
の溶解や芯物質(アミノ酸、ジペプチド、トリペプチド
又はそれらの塩)の溶出がほとんどなく高品質で実用性
の亮い上記芯物質を油脂で被覆したマイクロカプセルを
得ることができることを知見し1本発明をなすに至った
。In order to achieve the above object, the present inventor has made extensive studies and found that one or more core substances selected from amino acids, dipeptides, tripeptides, and salts thereof are coated with oil or fat. In this case, an alkylene glycol having a molecular weight of 60 to 400, which hardly dissolves the core substance and fats and oils, is used as the encapsulation medium, and the core substance is preferably
After being dispersed in fats and oils heated to 0 to 100°C, this core substance dispersion slurry is preferably added and dispersed in an alkylene glycol having the above molecular weight heated to 40 to 100°C, and the slurry is then rapidly cooled. In alkylene glycol, fats and oils that have a high affinity with amino acids form a film with excellent coating properties on the surface of the core substance, and therefore, the film material (fats and oils)
We discovered that it is possible to obtain microcapsules in which the core substance is coated with oil and fat, which is of high quality and highly practical, with almost no dissolution of the core substance or elution of the core substance (amino acids, dipeptides, tripeptides, or their salts). He came up with an invention.
従って、本発明は、アミノ酸、ジペプチド、トリペプチ
ド及びそれらの塩から選ばれる1種又は2種以上の芯物
質を油脂中に分散した後、該芯物質分散スラリーを分子
JL60〜400のアルキレングルコール中に添加1分
散して、上記芯物質を油脂で被覆したマイクロカプセル
を得ることを特徴とするマイクロカプセルの製造方法を
提供する。Therefore, in the present invention, after dispersing one or more core substances selected from amino acids, dipeptides, tripeptides, and salts thereof in fats and oils, the core substance dispersion slurry is mixed with an alkylene glycol having a molecular JL of 60 to 400. The present invention provides a method for producing microcapsules, which comprises adding and dispersing the above-mentioned core substance in a liquid to obtain microcapsules in which the core substance is coated with oil or fat.
以下1本発明につき更に詳しく説明する。The present invention will be explained in more detail below.
本発明のマイクロカプセルの製造方法で膜材として使用
する油脂としては、特に限定されないが、融点が100
℃以下、特に40〜80℃以下で、かつ熱に対して安定
であり、アミノ酸を変性させることもなく、人や他の動
物の消化酵素で容易に消化し得るもの、例えば硬化魚油
、硬化鯨油、硬化牛脂等の動物性油、硬化ヒマシ油、硬
化大豆油。The oil and fat used as the membrane material in the method for producing microcapsules of the present invention is not particularly limited, but has a melting point of 100
℃ or lower, especially 40 to 80℃ or lower, is stable against heat, does not denature amino acids, and can be easily digested by human or other animal digestive enzymes, such as hydrogenated fish oil and hydrogenated whale oil. , animal oils such as hydrogenated beef tallow, hydrogenated castor oil, and hydrogenated soybean oil.
硬化パーム油、パームステアリン等の植物性油などが好
適に使用し得る。なお、これら油脂は、単独で使用して
も混合して使用してもよく、更に硬化油に未硬化油を混
合して使用することも可能である。Vegetable oils such as hardened palm oil and palm stearin can be suitably used. Note that these oils and fats may be used alone or in combination, and it is also possible to use a mixture of hardened oil and unhardened oil.
また、芯物質としては、アミノ酸、ジペプチド、トリペ
プチド及びそれらの塩から選ばれる1種又は2種以上を
使用するもので、この場合、マイクロカプセルの使用目
的に応じて種々のアミノ酸やペプチドを用いることがで
きる。芯物質として具体的には、L−バリン、L−ロイ
シン、L−イソロイシン、L−スレオニン、L−フェニ
ルアラニン、L−トリプトファン、L−リジン、DL−
メチオニン、L−ヒスチジン等の必須アミノ酸や、L−
グルタミン、L−グルタミン酸、L−アスパラギン、L
−アスパラギン酸などのL型アミノ酸やこれらのD型又
はdQ型アミノ酸等のアミノ酸類、グリシルグリシン(
Gly−Gly) 、ロイシルグリシン(Leu G
ly)、グリシルヒスチジン(Gly−His) 、
グリシルリジン(Gly Lys) 1アラニルグリ
シン(Ala−aly) 、グリシルアスパラギン酸(
Gly Asp) Iセリルグリシン(Set−Gl
y) 、グリシルロイシルアラニン(Gly −Leu
−Ala) 、グリシルリシルグリシン(Gly −
Lys −Gly)等のジ又はトリペプチドなど、更に
はこれら化合物のアルカリ金属塩又はアルカリ土類金属
塩などが例示される。なお、これら化合物は、1種を単
独で又は2種以上を混合して使用することができる。In addition, as the core substance, one or more types selected from amino acids, dipeptides, tripeptides, and salts thereof are used. In this case, various amino acids and peptides are used depending on the purpose of use of the microcapsules. be able to. Specifically, the core substances include L-valine, L-leucine, L-isoleucine, L-threonine, L-phenylalanine, L-tryptophan, L-lysine, and DL-
Essential amino acids such as methionine and L-histidine, and L-
Glutamine, L-glutamic acid, L-asparagine, L
-Amino acids such as L-type amino acids such as aspartic acid and these D-type or dQ-type amino acids, glycylglycine (
Gly-Gly), leucylglycine (Leu G
ly), glycylhistidine (Gly-His),
Glycyrrhizine (Gly Lys) 1 Alanylglycine (Ala-aly), Glycylaspartic acid (
Gly Asp) I Serylglycine (Set-Gl
y), glycylleucylalanine (Gly-Leu
-Ala), glycylysylglycine (Gly-
Examples include di- or tripeptides such as Lys-Gly), and alkali metal salts or alkaline earth metal salts of these compounds. In addition, these compounds can be used individually or in mixture of 2 or more types.
更に、芯物質として用いるアミノ酸及びペプチドは、数
分のltmから数100/a、特に50例以下の大きさ
であることが、マイクロカプセル中への内蔵性や取扱い
性から好ましく1粒子が大きい場合は微粉砕して使用す
ることが好適である。Furthermore, the amino acids and peptides used as the core material preferably have a size of from a few minutes to several 100/a, especially 50 or less, from the viewpoint of ease of inclusion in microcapsules and ease of handling, when one particle is large. is preferably used after being finely pulverized.
なお、膜材や芯物質中に油脂又はアミノ酸、ペプチドと
共に添加剤としてトコフェロール等の酸化防止剤、色素
、香料などを所望量添加することは、何ら差し支えない
。Note that there is no problem in adding desired amounts of antioxidants such as tocopherol, pigments, fragrances, etc. as additives together with oils, fats, amino acids, and peptides into the membrane material and core material.
而して、本発明のマイクロカプセルの製造方法は、上記
芯物質を油脂中に分散した後、この分散スラリーを分子
量60〜400のアルキレングルコール中に添加8分散
するものであり、このようにカプセル化媒体として油脂
やアミノ酸を溶解したり変性させたりすることがなく、
かつ熱に対して安定で、加熱時に300〜100センチ
ポイズ程度の粘度を有する分子量60〜400のアルキ
レングルコールを使用することにより、このアルキレン
グルコール中でアミノ酸との親和性が高い油脂が芯物質
表面に被覆性の良好な被膜を形成するものである。Therefore, the method for producing microcapsules of the present invention involves dispersing the above-mentioned core substance in oil and fat, and then adding and dispersing this dispersion slurry in alkylene glycol having a molecular weight of 60 to 400. As an encapsulation medium, it does not dissolve or denature oils, fats, or amino acids.
By using an alkylene glycol with a molecular weight of 60 to 400 that is stable against heat and has a viscosity of about 300 to 100 centipoise when heated, oils and fats that have a high affinity with amino acids in this alkylene glycol are used as the core substance. It forms a film with good coverage on the surface.
この場合、分子量60〜400のアルキレングルコール
としては1例えばエチレングリコール。In this case, the alkylene glycol having a molecular weight of 60 to 400 is 1, for example, ethylene glycol.
1.2−プロパンジオール、1,3−プロパンジオール
、1,4−ブタンジオール等のグリコール類、ジエチレ
ングリコール、トリエチレングリコール、テトラエチレ
ングリコール、ポリエチレングリコール#400.ジプ
ロピレングリコール#400、トリプロピレングリコー
ル#400.テトラプロピレングリコール#400等の
ポリアルキレンゲリコール類が挙げられるが、特にプロ
ピレングリコール、エチレングリコール、ジ、トリ。1. Glycols such as 2-propanediol, 1,3-propanediol, 1,4-butanediol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol #400. Dipropylene glycol #400, tripropylene glycol #400. Examples include polyalkylene glycols such as tetrapropylene glycol #400, particularly propylene glycol, ethylene glycol, di- and tri-glycols.
テトラエチレングリコール、ジ、トリ、テトラプロピレ
ングリコールが好適に使用できる。Tetraethylene glycol, di-, tri-, and tetrapropylene glycol can be suitably used.
ここで、芯物質を油脂中に分散する場合は、油脂を40
〜100℃、特に50〜90℃に加熱し、この加熱油脂
中に上記芯物質を油脂中の含有率が1〜80%(重量%
、以下同様)、特に30〜70%となるように添加し、
撹拌して分散することが好ましい。Here, when dispersing the core substance in oil or fat, add 40% of the oil or fat.
The above-mentioned core substance is heated to ~100°C, particularly 50 to 90°C, and the content of the core substance in the heated fat is 1 to 80% (wt%).
, hereinafter the same), especially added to 30 to 70%,
It is preferable to disperse by stirring.
次いで、得られた芯物質分散スラリーを上記特定分子量
のアルキレングルコール中に添加、分散してカプセル化
を行なうが、この場合、アルキレングルコールを分散ス
ラリー(芯物質+油脂)量とアルキレングルコールとの
比率が重量比で1/2〜1/30.特に115〜1/1
0となるように使用し、40〜100℃、特に50〜9
0”Cに加熱した後に分散スラリーを添加1分散して、
マイクロカプセルの粒径を数p〜数I、特に200〜8
oOpに調整することが好ましい。Next, the obtained core material dispersion slurry is added and dispersed in alkylene glycol having the above-mentioned specific molecular weight to perform encapsulation. The ratio by weight is 1/2 to 1/30. Especially 115~1/1
0 to 40 to 100℃, especially 50 to 9
After heating to 0"C, add and disperse the dispersion slurry,
The particle size of the microcapsules is from several parts to several parts, especially from 200 to 8
It is preferable to adjust to oOp.
なお、芯物質分散スラリーをアルキレングルコールレこ
、添加2分散してカプセル化を行なう場合、まず少量、
好ましくは分散スラリーとフルキレンゲルコールとの比
率が重量比で1:0.25〜1:5になるような量のア
ルキレングルコールを芯物質分散スラリーに加えて第1
段カプセル化を行なった後、この第1段カプセルを残り
のアルキレングルコールに投入して第2段カプセル化を
行なう方法を好適に採用し得る。この場合、第1段カプ
セル化の温度は40〜100℃、特に50〜90℃、第
2段カプセル化の温度は40〜100℃、特に50〜9
0℃とすることが好適である。In addition, when performing encapsulation by dispersing the core material dispersion slurry with alkylene glycol, first add a small amount of
Preferably, alkylene glycol is added to the core material dispersion slurry in an amount such that the ratio of the dispersion slurry to fullkylene gelcol is 1:0.25 to 1:5 by weight.
After performing stage encapsulation, a method may be suitably employed in which the first stage capsules are added to the remaining alkylene glycol to perform second stage encapsulation. In this case, the temperature of the first stage encapsulation is 40-100 °C, especially 50-90 °C, and the temperature of the second stage encapsulation is 40-100 °C, especially 50-90 °C.
The temperature is preferably 0°C.
引き続いて、このアルキレングルコールの液温を急激に
下げ、好ましくは40℃以下にすると、膜材である油脂
が凝固し、カプセル化が終了する。Subsequently, when the liquid temperature of this alkylene glycol is rapidly lowered, preferably to 40° C. or lower, the oil or fat that is the membrane material solidifies, and encapsulation is completed.
このようにして得られたアミノ酸及び/又はペプチド含
有油脂マイクロカプセルは、使用目的等に応じて、アル
キレングルコール中からマイクロカプセルを分取し、こ
のマイクロカプセルを再度エタノール等の溶媒に分散さ
せて液状として、あるいはマイクロカプセル表面にトウ
モロコシデンプン、バレイショデンプン等の微粉末をコ
ーティングさせて粉末状として、各種食品、医薬品等と
して利用することができる。The amino acid and/or peptide-containing oil microcapsules obtained in this way can be prepared by separating the microcapsules from alkylene glycol and redispersing them in a solvent such as ethanol, depending on the purpose of use. It can be used as a liquid, or as a powder by coating the surface of the microcapsule with a fine powder of corn starch, potato starch, etc., as various foods, medicines, etc.
λ吋例弥果
本発明の製造方法によれば、膜材(油脂)の溶解や芯物
質(アミノ酸及び/又はペプチド)の溶出がほとんどな
い高品質で実用的なアミノ酸及び/又はペプチド含有油
脂マイクロカプセルを経済的に有利にかつ簡単に製造す
ることができる。更に、本発明においては、水溶性及び
難溶性のアミノ酸やペプチドのカプセル化が可能で、ア
ミノ酸由来の苦味をカプセル中に隠蔽することができる
ので、得られるマイクロカプセルを健康食品、医療用食
品等として幅広く利用することができ、例えば必須アミ
ノ酸を芯物質として、食事が自刃で摂取できない人のた
めの高栄養価流動食など、いろいろな機能生食品として
応用できる。According to the production method of the present invention, a high-quality and practical amino acid and/or peptide-containing oil microorganism is produced that hardly dissolves the membrane material (oil or fat) or elutes the core substance (amino acid and/or peptide). Capsules can be produced economically and easily. Furthermore, in the present invention, it is possible to encapsulate water-soluble and poorly soluble amino acids and peptides, and the bitter taste derived from amino acids can be hidden in the capsules, so the resulting microcapsules can be used as health foods, medical foods, etc. For example, it can be used in a variety of functional raw foods, including essential amino acids as a core substance, and highly nutritious liquid food for people who cannot consume their own meals.
失11−皮絞孤
以下、実施例及び比較例を示し、本発明を具体的に説明
するが、本発明は下記実施例に制限されるものではない
。EXAMPLE 11 - Skin Squeezing The present invention will be specifically explained below with reference to Examples and Comparative Examples, but the present invention is not limited to the Examples below.
〔実施例1〕
硬化牛脂40gと第1表に示すアミノ酸60gとを30
0aQの撹拌槽に入れ、温度70℃で加熱。[Example 1] 40 g of hardened beef tallow and 60 g of the amino acids shown in Table 1 were
Place in a 0aQ stirring tank and heat at 70°C.
混合した後、これにプロピレンゲルコール50gを入れ
、第1段カプセル化を行なった。After mixing, 50 g of propylene gelcol was added thereto to perform first-stage encapsulation.
次に、3Qの撹拌槽にプロピレンゲルコールlQを入れ
、90℃に加熱して撹拌下、上で得られた第1段カプセ
ルを添加9分散して第2段カプセル化を行なった後、系
内の温度を急激に下げ、アミノ酸を芯物質とするマイク
ロカプセルの分散液を得た。このマイクロカプセル分散
液を濾過して溶媒を除去し、更にマイクロカプセルをエ
チルアルコールで洗浄し、乾燥したところ1粒径が14
0〜400pの範囲で比較的揃ったアミノ酸含有マイク
ロカプセルが得られた。Next, propylene gelcol 1Q was placed in the stirring tank of 3Q, heated to 90°C, and while stirring, the first stage capsules obtained above were added and dispersed to perform second stage encapsulation. The internal temperature was rapidly lowered to obtain a dispersion of microcapsules containing amino acids as the core material. This microcapsule dispersion was filtered to remove the solvent, and the microcapsules were washed with ethyl alcohol and dried, resulting in a particle size of 14.
Amino acid-containing microcapsules with relatively uniform amino acids in the range of 0 to 400p were obtained.
〔実施例2〕
第1段マイクロカプセルを行なわずに硬化牛脂とアミノ
酸との混合物を直接プロピレンゲルコールに分散する以
外は、実施例1と同様にしてマイクロカプセルを得た。[Example 2] Microcapsules were obtained in the same manner as in Example 1, except that the mixture of hardened beef tallow and amino acids was directly dispersed in propylene gelcol without performing the first stage microcapsule formation.
〔実施例3〕
第2段カプセル化におけるカプセル化媒体(プロピレン
ゲルコール)の温度を90℃から70℃に変えた以外は
、実施例1と同様にしてマイクロカプセルを得た。[Example 3] Microcapsules were obtained in the same manner as in Example 1, except that the temperature of the encapsulation medium (propylene gelcol) in the second stage encapsulation was changed from 90°C to 70°C.
〔実施例4〕
膜物質として硬化牛脂の代わりに硬化牛脂と牛脂(50
:50.重量比、以下同様)の混合油脂を用いる以外は
、実施例1と同様にしてマイクロカプセルを得た。[Example 4] Cured beef tallow and beef tallow (50%
:50. Microcapsules were obtained in the same manner as in Example 1, except that a mixed fat and oil having a weight ratio (the same applies hereinafter) was used.
〔実施例5〕
膜物質として硬化牛脂の代わりに硬化牛脂と大豆油(6
0:40)の混合油脂を用いる以外は、実施例1と同様
にしてマイクロカプセルを得た。[Example 5] Hydrogenated beef tallow and soybean oil (6
Microcapsules were obtained in the same manner as in Example 1, except that a mixed oil and fat of 0:40) was used.
〔実施例6〕
膜物質として硬化牛脂の代わりにパームステアリンと大
豆油(60:40)の混合油脂を用いる以外は、実施例
1と同様にしてマイクロカプセルを得た。[Example 6] Microcapsules were obtained in the same manner as in Example 1, except that a mixed fat of palm stearin and soybean oil (60:40) was used instead of hardened beef tallow as the membrane material.
〔実施例7〕
第1段及び第2段カプセル化媒体としてプロピレンゲル
コールの代わりにエチレングリコールを用いる以外は、
実施例1と同様にしてマイクロカプセルを得た。[Example 7] Except that ethylene glycol was used instead of propylene gelcol as the first and second stage encapsulation media.
Microcapsules were obtained in the same manner as in Example 1.
〔比較例1〕
第1段及び第2段カプセル化媒体としてプロピレンゲル
コールの代わりにグリセリンを用いる以外は、実施例1
と同様にしてマイクロカプセルを得た。[Comparative Example 1] Example 1 except that glycerin was used instead of propylene gelcol as the first and second stage encapsulation media.
Microcapsules were obtained in the same manner.
〔比較例2〕
第1段及び第2段カプセル化媒体としてプロピレンゲル
コールの代わりにグリセリン:メタノール(2:1)の
混合溶媒を用いる以外は、実施例1と同様にしてマイク
ロカプセルを得た。[Comparative Example 2] Microcapsules were obtained in the same manner as in Example 1, except that a mixed solvent of glycerin:methanol (2:1) was used instead of propylene gelcol as the first and second stage encapsulation media. .
第1表に上記各側の使用物質及び反応温度条件を列記す
ると共に、得られたマイクロカプセルの試験結果を示す
。Table 1 lists the materials used and reaction temperature conditions for each side, and also shows the test results of the obtained microcapsules.
なお、マイクロカプセルの試験は以下のように行なった
。The microcapsule test was conducted as follows.
撹拌し、均一分散した試験液をスライドガラスに採取し
、顕微鏡で下記事項についてlll察を行なった。The test solution was stirred and uniformly dispersed and collected on a slide glass, and the following items were observed using a microscope.
(1)カプセル化率 油脂中に完全に芯物質がカプセル化している割合。(1) Encapsulation rate The percentage of core substances completely encapsulated in fats and oils.
(2)アミノ酸残存率 カプセル化せずに溶媒中に分散している芯物質の割合。(2) Amino acid survival rate Percentage of core material dispersed in the solvent without encapsulation.
上記amは同一サンプルについて3回行ない、平均値を
結果とした。The above am was performed three times on the same sample, and the average value was used as the result.
第1表の結果より、カプセル化媒体としてプロピレンゲ
ルコールやエチレングリコールを用いた本発明の製造方
法によれば、膜物質の溶解や芯物質の溶出がない良好な
状態のアミノ酸及び/又はペプチド含有油脂マイクロカ
プセルが得られることが確認された。From the results in Table 1, it is clear that according to the production method of the present invention using propylene gelcol or ethylene glycol as the encapsulation medium, amino acids and/or peptides containing amino acids and/or peptides in good condition with no dissolution of membrane substances or elution of core substances. It was confirmed that oil and fat microcapsules were obtained.
〔実施例8〕
第1段及び第2段のカプセル化媒体として、プロピレン
ゲルコールの代わりにテトラプロピレンゲルコールを用
いる以外は実施例1と同様にしてマイクロカプセルを得
た。[Example 8] Microcapsules were obtained in the same manner as in Example 1, except that tetrapropylene gelcol was used instead of propylene gelcol as the encapsulation medium in the first and second stages.
〔実施例9〕
芯物質であるアミノ酸をグルタミルグルタミンに代えた
以外は実施例1と同様にしてマイクロカプセルを得た。[Example 9] Microcapsules were obtained in the same manner as in Example 1 except that the amino acid as the core substance was replaced with glutamylglutamine.
上記実施例8及び9のカプセルはいずれも上記実施例7
と同様の結果を有していた。The capsules of Examples 8 and 9 above are both of the capsules of Example 7 above.
had similar results.
出願人 ラ イ オ ン 株式会社 代理人 弁理士 小 島 隆 司Applicant: Laion Co., Ltd. Agent: Patent Attorney Takashi Kojima
Claims (1)
塩から選ばれる1種又は2種以上の芯物質を油脂中に分
散した後、該芯物質分散スラリーを分子量60〜400
のアルキレングルコール中に添加、分散して、上記芯物
質を油脂で被覆したマイクロカプセルを得ることを特徴
とするマイクロカプセルの製造方法。1. After dispersing one or more core substances selected from amino acids, dipeptides, tripeptides, and salts thereof in fats and oils, the core substance dispersion slurry has a molecular weight of 60 to 400.
A method for producing microcapsules, which comprises adding and dispersing the core substance in alkylene glycol to obtain microcapsules in which the core substance is coated with oil or fat.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP63235390A JPH0283031A (en) | 1988-09-20 | 1988-09-20 | Preparation of microcapsule |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP63235390A JPH0283031A (en) | 1988-09-20 | 1988-09-20 | Preparation of microcapsule |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH0283031A true JPH0283031A (en) | 1990-03-23 |
Family
ID=16985374
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP63235390A Pending JPH0283031A (en) | 1988-09-20 | 1988-09-20 | Preparation of microcapsule |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0283031A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014063985A3 (en) * | 2012-10-25 | 2014-07-31 | Nestec S.A. | Encapsulated bitter peptides, methods of encapsulating bitter peptides, and nutritional compositions including encapsulated bitter peptides |
JP2016029915A (en) * | 2014-07-29 | 2016-03-07 | 学校法人福岡大学 | Functional polymer composite particle using carbon dioxide and a carbon dioxide-phile type surfactant and method for producing the same |
-
1988
- 1988-09-20 JP JP63235390A patent/JPH0283031A/en active Pending
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014063985A3 (en) * | 2012-10-25 | 2014-07-31 | Nestec S.A. | Encapsulated bitter peptides, methods of encapsulating bitter peptides, and nutritional compositions including encapsulated bitter peptides |
JP2015536136A (en) * | 2012-10-25 | 2015-12-21 | ネステク ソシエテ アノニム | Encapsulated bitter peptide, method for encapsulating bitter peptide, and nutritional composition containing encapsulated bitter peptide |
JP2016029915A (en) * | 2014-07-29 | 2016-03-07 | 学校法人福岡大学 | Functional polymer composite particle using carbon dioxide and a carbon dioxide-phile type surfactant and method for producing the same |
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