JPH0358264B2 - - Google Patents
Info
- Publication number
- JPH0358264B2 JPH0358264B2 JP61313550A JP31355086A JPH0358264B2 JP H0358264 B2 JPH0358264 B2 JP H0358264B2 JP 61313550 A JP61313550 A JP 61313550A JP 31355086 A JP31355086 A JP 31355086A JP H0358264 B2 JPH0358264 B2 JP H0358264B2
- Authority
- JP
- Japan
- Prior art keywords
- water
- powder
- vitamin
- coating
- soluble
- 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.)
- Expired - Lifetime
Links
- 229940088594 vitamin Drugs 0.000 claims description 44
- 229930003231 vitamin Natural products 0.000 claims description 44
- 235000013343 vitamin Nutrition 0.000 claims description 43
- 239000011782 vitamin Substances 0.000 claims description 43
- 239000000843 powder Substances 0.000 claims description 36
- 239000011248 coating agent Substances 0.000 claims description 32
- 238000000576 coating method Methods 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 20
- 239000011162 core material Substances 0.000 claims description 17
- 150000003722 vitamin derivatives Chemical class 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 13
- 150000002632 lipids Chemical class 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 9
- 238000002844 melting Methods 0.000 claims description 9
- 230000008018 melting Effects 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- 238000009472 formulation Methods 0.000 claims description 3
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 18
- 239000002245 particle Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- JZRWCGZRTZMZEH-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 229960003512 nicotinic acid Drugs 0.000 description 9
- 235000001968 nicotinic acid Nutrition 0.000 description 9
- 239000011664 nicotinic acid Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- -1 etc. Chemical compound 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 235000013305 food Nutrition 0.000 description 4
- 235000019157 thiamine Nutrition 0.000 description 4
- 239000011721 thiamine Substances 0.000 description 4
- 239000001993 wax Substances 0.000 description 4
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- UIERGBJEBXXIGO-UHFFFAOYSA-N thiamine mononitrate Chemical compound [O-][N+]([O-])=O.CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N UIERGBJEBXXIGO-UHFFFAOYSA-N 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 229910001369 Brass Inorganic materials 0.000 description 2
- 229930003270 Vitamin B Natural products 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000003674 animal food additive Substances 0.000 description 2
- 235000015278 beef Nutrition 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N beta-monoglyceryl stearate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- 239000010951 brass Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000007922 dissolution test Methods 0.000 description 2
- 235000019688 fish Nutrition 0.000 description 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 238000009372 pisciculture Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- 229960003495 thiamine Drugs 0.000 description 2
- 235000019156 vitamin B Nutrition 0.000 description 2
- 239000011720 vitamin B Substances 0.000 description 2
- RBCOYOYDYNXAFA-UHFFFAOYSA-L (5-hydroxy-4,6-dimethylpyridin-3-yl)methyl phosphate Chemical compound CC1=NC=C(COP([O-])([O-])=O)C(C)=C1O RBCOYOYDYNXAFA-UHFFFAOYSA-L 0.000 description 1
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 description 1
- 241001454694 Clupeiformes Species 0.000 description 1
- AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- 229930186217 Glycolipid Natural products 0.000 description 1
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 1
- VAYOSLLFUXYJDT-RDTXWAMCSA-N Lysergic acid diethylamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N(CC)CC)C2)=C3C2=CNC3=C1 VAYOSLLFUXYJDT-RDTXWAMCSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- YDBYJHTYSHBBAU-YFKPBYRVSA-N S-methyl-L-methioninate Chemical compound C[S+](C)CC[C@H](N)C([O-])=O YDBYJHTYSHBBAU-YFKPBYRVSA-N 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 229930003316 Vitamin D Natural products 0.000 description 1
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 229930003448 Vitamin K Natural products 0.000 description 1
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 235000019513 anchovy Nutrition 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 229960002685 biotin Drugs 0.000 description 1
- 239000011616 biotin Substances 0.000 description 1
- 235000020958 biotin Nutrition 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- FDJOLVPMNUYSCM-UVKKECPRSA-L cobalt(3+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2,7, Chemical compound [Co+3].N#[C-].C1([C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@@H](C)OP([O-])(=O)O[C@H]3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)[N-]\C2=C(C)/C([C@H](C\2(C)C)CCC(N)=O)=N/C/2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O FDJOLVPMNUYSCM-UVKKECPRSA-L 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 229960000304 folic acid Drugs 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002306 glutamic acid derivatives Chemical class 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000008173 hydrogenated soybean oil Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
- 229960000367 inositol Drugs 0.000 description 1
- AGBQKNBQESQNJD-UHFFFAOYSA-M lipoate Chemical compound [O-]C(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-M 0.000 description 1
- 235000019136 lipoic acid Nutrition 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Chemical class 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- ZQTHOIGMSJMBLM-BUJSFMDZSA-N pangamic acid Chemical compound CN(C)CC(=O)OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O ZQTHOIGMSJMBLM-BUJSFMDZSA-N 0.000 description 1
- 229940055726 pantothenic acid Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229960002477 riboflavin Drugs 0.000 description 1
- 235000019192 riboflavin Nutrition 0.000 description 1
- 239000002151 riboflavin Substances 0.000 description 1
- IKGXIBQEEMLURG-NVPNHPEKSA-N rutin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-NVPNHPEKSA-N 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 108010093489 thiaminase II Proteins 0.000 description 1
- 229960002663 thioctic acid Drugs 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 150000003710 vitamin D derivatives Chemical class 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 235000019168 vitamin K Nutrition 0.000 description 1
- 239000011712 vitamin K Substances 0.000 description 1
- 150000003721 vitamin K derivatives Chemical class 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 229940046008 vitamin d Drugs 0.000 description 1
- 229940046010 vitamin k Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
<産業上の利用分野>
本発明は食品・飼料等の分野において添加剤と
して添加する水溶性ビタミン類の被覆製剤の製造
方法に関するものである。
<従来の技術>
水溶性ビタミン類の被覆製剤の製造方法に関す
る研究は従来からなされており、おおよそ二通り
の従来方法が一般的になつている。一方法では溶
解した硬化油、ワツクス等に水溶性ビタミン類を
懸濁させた後、スプレー又は回転デイスクを用い
て噴霧冷却固化することにより被覆物を得るもの
である(例えば、特公昭50−13192号公報に記載
の「養魚用生餌飼料組生物」、特開昭58−205461
号公報に記載の「養魚用飼料」等)。他の方法に
おいては、流動層法と呼ばれる方法で水溶性ビタ
ミン類を下部からの風力で浮き上がらせておき上
部から硬化油又はワツクス等の溶解した被覆剤を
噴霧して被覆を行うか、又はこれに類似した方法
によるものである(例えば、特開昭50−52221号
公報に記載の「ビタミン粒子材料を被覆する方
法」等)。
<発明が解決しようとする問題点>
水溶性ビタミン類の被覆製剤は食品添加物、飼
料添加にビタミンの補強剤として使用されてお
り、その被覆性能を非常に重要である。飼料添加
物、特に養魚用添加物として用いられる場合、原
料の魚体中に含まれるチアミナーゼによりチアミ
ン(ビタミンB1)が分解し、それが原因となり
養魚のチアミン欠乏症によるへい死が起こつい
る。また、その他のビタミン類においても、外部
からの水分・光・熱及びPHなどによりビタミンと
しての効力が失いやすい。また、食品の添加する
場合には、各種ビタミン類の臭気や味が食品に悪
影響を与える場合があるが、被覆によりマスキン
グできる。しかし、従来開発された方法は被覆が
不十分であり上記の使用に対して十分な性能が発
揮されていない。
また、芯物質である水溶性ビタミン類の含量が
低いため、使用にあたつて多量の被覆製剤の添加
が必要であり、ひいてはコストアツプの原因とな
つていた。
さらに、被覆剤を溶融して噴霧し、又は流動層
を形成するためには多大のエネルギーを消費しな
ければならず、その装置のメインテナンスを含め
て作業が煩雑であつた。
<発明の目的>
従つて、本発明の目的は十分な被覆が可能な水
溶性ビタミン類被覆製剤の製造方法を提供するこ
とである。
本発明の別の目的は、被覆剤を溶融する必要が
なく、従つて多大のエネルギーの消費が回避で
き、また使用装置の維持の容易な水溶性ビタミン
類の製造方法を提供することである。
本発明の更に別の目的は、芯物質である水溶性
ビタミン類の含量が高いため、少量の被覆製剤を
使用すれば、ビタミンとしての十分な効果が得ら
れ、従つて要するコストを減少できる水溶性ビタ
ミン類被覆製剤の製造方法を提供することであ
る。
<問題点を解決するための手段>
本発明によれば、水溶性ビタミン粉状体に、皮
膚物質として融点40℃以上の脂質粉状体を接触・
衝突させ、上記水溶性ビタミン類粉状体の全周囲
表面に上記脂質粉状体を付着・被覆し、水溶性ビ
タミン類を芯物質として脂質が被覆されさ製剤を
製造することを特徴とする水溶性ビタミン類被覆
製剤の製造方法が提供される。
<発明の説明>
本発明によれば、芯物質である水溶性ビタミン
類は天然に存在するものでも合成により得られる
ものでもよく、その性状は常温で結晶状・粉末状
を問わない。そのまま被覆製剤の原料に用いるこ
とができ、また水溶性成分もしくは油性物により
造粒もしくは予備被覆してもよい。本発明におい
て好ましく使用できる水溶性ビタミン類としては
ビタミンB1、ビタインB2、ビタミンB6、ビタミ
ンB12、ビタミンB13、ビタミンB14、ビタミン
B15、リポ酸、ニコチン酸、ニコチンアミド、パ
ントテン酸、葉酸、パラアミノ安息香酸、ビオチ
ン、コリン、イノシトール、ビタミンL、ビタミ
ンU、ビタミンC、ビタミンP等を挙げることが
でし、またビタミンA、ビタミンD、ビタミン
E、ビタミンKなどの油溶性ビタミンの水溶性誘
導体も挙げることができる。また、上記のビタミ
ン類のカルシウム塩、ナトリウム塩、カリウム塩
及びその他の金属塩、さらには塩酸塩、硝酸塩等
の塩、リン酸エステル、酢酸エステル、コハク酸
エステル、マレイン酸テステル、グルタミン酸エ
ステル等の他の誘導体も水溶性ビタミン類として
使用できる。これらのうちから用途に応じては二
種以上の上記水溶性ビタミン類を組み合わせて使
用することもできる。また、水溶性ビタミン類の
造粒・予備被覆に用いることができる水溶性成分
としては、糖、蛋白質、アミノ酸、無機塩等があ
る。油性物としては天然油脂、硬化油、ワツク
ス、脂肪酸モノグリセライド、脂肪酸ジグリセラ
イド、脂肪酸及びその他の脂質が使用できる。さ
らに、その他の成分として天然又は合成に由来す
る有機・無機高分子物質等を挙げることができ
る。
被覆剤である融点40℃以上の脂質粉状体として
は天然に得られる動植物油、例えば牛脂、牛脂硬
化油、魚油硬化油、大豆硬化油、脂肪酸モノグリ
セライド、脂肪酸ジグリセライド、プロピレング
リコール脂肪酸エステル、シヨ糖脂肪酸エステ
ル、脂肪酸、脂肪酸塩、高級アルコール、ワツク
ス、リン又は窒素含有リン脂質、糖を構成成分に
持つ糖脂質、スルホン酸基を持つスルホリピツ
ド、ステロール、炭化水素及びこれらの水添物等
のうち一種または二種以上のものから選ぶことが
できる。融点が40℃未満では好ましい脂質粉状体
が得られず、良好な被覆製剤が得られなかつた。
芯物質である水溶性ビタミン類を含有する粉体
と被覆剤である融点40℃以上の粉末状脂質とを互
いに接触・衝突させる方法としては、公知のボー
ルミル、電気乳鉢、高能率粉体混合装置、高速気
流の対流により粉体を接触させる装置等を使用す
ることができ、これにより粉状体を互いに接触衝
突させると共に装置内壁及び補助具と衝突させて
均一に被覆する。接触・衝突においては、激しす
ぎる条件で作用させると、芯物質の粉砕が起こる
危険があるため、温和な条件で接触させることが
望ましい。また、上記装置により接触させるにあ
たつて、あらかじめ芯物質粉状体と被覆剤粉状体
とを予備混合することにより被覆性能を向上させ
ることができる。
芯物質と被覆剤との混合比(芯物質粉状体重
量/被覆剤粉状体重量)は0.1〜50の範囲で用い
ることが可能であるが、粒径比との関係で調整す
ることが好ましい。粒径比が大きい場合には混合
比を大きくすることが好ましく、粒径比が小さい
場合には混合比を4以下にすることが望ましい。
単純に混合比を小さくすれば被覆性能が向上する
わけではなく、むしろ大きい方が性能が良い場合
もある。また、混合比が同じであつても、被覆剤
粉状体二以上に分割し、数回に分けて被覆するこ
とにより、被覆性能を向上させることができる。
いずれにしても、被覆剤が芯物質の全周囲表面
に被覆・付着していることが必要である。全周囲
表面に被覆・付着していないと、内部の芯物質が
外部に溶出してしまうためである。
<発明の効果>
本発明の方法により製造される被覆水溶性ビタ
ミン類製剤は、従来公知の製剤と比較して被覆性
能が大幅に向上し、その結果、他成分との接触が
防止できる。さらに、光、熱、水分及び外気から
の水溶性ビタミン類の遮断が可能となつた。従つ
て、食品や飼料の分野における使用に対して、各
種水溶性ビタミン類の有する効果が損なわれな
い。また、芯物質が外部へ放出する場合にも、
徐々に放出するために長期にわたつての効果が期
待できる。さらに、本発明の方法によれば製剤中
の水溶性ビタミン類の含量が増加するため、製剤
自体の添加量の減少が可能となり、従つて製剤使
用にあたつてのコストダウンが可能である。ま
た、本発明の製剤の製造方法は従来の製法と比較
して、エネルギー的にも作業性的にも簡便化が可
能である。
以上のように本発明の被覆製剤は従来にない多
くの効果を有しており、極めて有用である。
<実施例>
参考例 1
硝酸チアミン(平均粒径124μm、日本ロツシ
ユ社製品)400gを溶解した菜種硬化油(融点
64.1℃、日本油脂株式会社製)2Kgに添加後、ホ
モミキサーで十分に分散させた。この混合物を回
転デイスク型噴霧装置により30℃の室内に噴霧
し、粉末製品を得た。
参考例 2
溶解したカルナウバワツクス(融点83.7℃、野
田ワツクス社製)1.2Kgにニコチン酸(平均粒径
114μm、ジボダン社製品)800gを添加後、ホモ
ミキサーで十分に分散させた。以下参考例1と同
様の操作をすることにより、粉末製品を得た。
参考例 3
溶解したステアリン酸モノグリセライド(融点
64.7℃、理研ビタイン社製)1.2Kgにリボフラビ
ン(平均粒径146μm、日本ロツシユ社製品、商
品名ロビフラフ)600gを添加後、ホモミキサー
で十分に分散させた。以下参考例1と同様の操作
をすることにより、粒径が80〜250μmの粉末製
品を得た。
実施例 1
硝酸チアミン(平均粒径124μm、日本ロツシ
ユ社製品)42gと菜種硬化油(平均粒径8.6μm、
融点64.1℃、日本油脂株式会社製)18gを真ちゆ
う製のボール20個と共に遠心回転型混合機(岡田
精工社製、メカノミルーMM10)に入れ、回転速
度300r.p.m.で4時間混合した。得られた粉末を
参考例1により得られた粉末と共にカタクチイワ
シのミンチ中に硝酸チアミンとして10mg/100g
となるように添加し、30℃におけるチアミンの経
時的分解率を調べた。チアミンの測定方法は日本
薬局方に基づいて、抽出液に臭化シアン試液を加
えた後に波長368nmにおいて吸光度を測定するこ
とにより行つた。
<Industrial Application Field> The present invention relates to a method for producing a coated preparation of water-soluble vitamins to be added as an additive in the fields of food, feed, etc. <Prior Art> Research has been conducted on methods for producing coated preparations of water-soluble vitamins, and approximately two conventional methods have become common. One method is to obtain a coating by suspending water-soluble vitamins in dissolved hydrogenated oil, wax, etc., and then spraying and cooling using a spray or rotating disk to solidify (for example, Japanese Patent Publication No. 50-13192). "Live bait feed composition for fish farming" described in the publication, JP-A-58-205461
``Fish feed'' etc. described in the Publication No. 1). In other methods, water-soluble vitamins are floated by wind force from the bottom using a method called the fluidized bed method, and then a dissolved coating material such as hydrogenated oil or wax is sprayed from the top. (For example, ``Method of coating vitamin particle material'' described in Japanese Patent Application Laid-Open No. 50-52221, etc.). <Problems to be Solved by the Invention> Coated preparations of water-soluble vitamins are used as food additives and feed additives as vitamin reinforcing agents, and their coating performance is very important. When used as a feed additive, especially as an additive for fish farming, thiamin (vitamin B 1 ) is broken down by thiaminase contained in the raw fish body, which causes death due to thiamin deficiency in farmed fish. Also, other vitamins tend to lose their effectiveness as vitamins due to external moisture, light, heat, pH, etc. Furthermore, when added to food, the odor and taste of various vitamins may have an adverse effect on the food, but this can be masked by coating. However, conventionally developed methods provide insufficient coverage and do not exhibit sufficient performance for the above uses. Furthermore, since the content of water-soluble vitamins, which are core substances, is low, it is necessary to add a large amount of coating preparation before use, which is a cause of increased costs. Furthermore, it is necessary to consume a large amount of energy to melt and spray the coating material or to form a fluidized bed, and the work including the maintenance of the equipment is complicated. <Object of the Invention> Therefore, an object of the present invention is to provide a method for producing a water-soluble vitamin-coated preparation that allows sufficient coating. Another object of the present invention is to provide a method for producing water-soluble vitamins in which there is no need to melt the coating, thus avoiding the consumption of a large amount of energy, and in which the equipment used is easy to maintain. Still another object of the present invention is to provide water-soluble vitamins that have a high content of core substances, such as water-soluble vitamins, so that a sufficient effect as a vitamin can be obtained by using a small amount of coating preparation, and therefore, the cost can be reduced. An object of the present invention is to provide a method for producing a vitamin-coated preparation. <Means for solving the problem> According to the present invention, a water-soluble vitamin powder is contacted with a lipid powder having a melting point of 40°C or higher as a skin substance.
The water-soluble vitamin powder is made to collide with the water-soluble vitamin powder to adhere and coat the entire peripheral surface of the lipid powder, thereby producing a preparation coated with lipids using the water-soluble vitamins as a core material. A method for manufacturing a vitamin-coated preparation is provided. <Description of the Invention> According to the present invention, the water-soluble vitamins serving as the core substance may be naturally occurring or synthetically obtained, and their properties may be crystalline or powdery at room temperature. It can be used as it is as a raw material for coated preparations, or it may be granulated or pre-coated with a water-soluble component or an oily substance. Water-soluble vitamins that can be preferably used in the present invention include vitamin B 1 , vitamin B 2 , vitamin B 6 , vitamin B 12 , vitamin B 13 , vitamin B 14 , vitamin
B15 , lipoic acid, nicotinic acid, nicotinamide, pantothenic acid, folic acid, para-aminobenzoic acid, biotin, choline, inositol, vitamin L, vitamin U, vitamin C, vitamin P, etc., and vitamin A, Water-soluble derivatives of oil-soluble vitamins such as vitamin D, vitamin E and vitamin K may also be mentioned. In addition, calcium salts, sodium salts, potassium salts and other metal salts of the above vitamins, salts such as hydrochlorides and nitrates, phosphate esters, acetate esters, succinate esters, maleate esters, glutamate esters, etc. Other derivatives can also be used as water-soluble vitamins. Depending on the intended use, two or more of the above water-soluble vitamins may be used in combination. Furthermore, water-soluble components that can be used for granulation and pre-coating of water-soluble vitamins include sugars, proteins, amino acids, and inorganic salts. As oily substances, natural oils, hydrogenated oils, waxes, fatty acid monoglycerides, fatty acid diglycerides, fatty acids and other lipids can be used. Furthermore, other components may include organic and inorganic polymeric substances derived from natural or synthetic sources. The lipid powder with a melting point of 40°C or higher used as a coating agent includes naturally occurring animal and vegetable oils such as beef tallow, hydrogenated beef tallow oil, hydrogenated fish oil, hydrogenated soybean oil, fatty acid monoglyceride, fatty acid diglyceride, propylene glycol fatty acid ester, and sucrose. Fatty acid esters, fatty acids, fatty acid salts, higher alcohols, waxes, phosphorus- or nitrogen-containing phospholipids, glycolipids with sugar as a constituent, sulfolipids with sulfonic acid groups, sterols, hydrocarbons, and hydrogenated products of these, etc. Or you can choose from two or more types. If the melting point was less than 40°C, a desirable lipid powder could not be obtained, and a good coating preparation could not be obtained. The method of bringing the powder containing water-soluble vitamins, which is the core substance, and the powdered lipid, which is the coating agent, into contact with each other and collides with each other is to use a known ball mill, electric mortar, or high-efficiency powder mixing device. It is possible to use a device that brings the powder into contact with each other by convection of high-speed air currents, thereby causing the powder to come into contact with each other and collide with the inner wall of the device and the auxiliary tool to uniformly coat the powder. When contacting and colliding, it is preferable to bring the materials into contact under mild conditions, as there is a risk of pulverization of the core material if the action is too violent. Moreover, the coating performance can be improved by premixing the core material powder and the coating agent powder in advance when bringing them into contact with each other using the above-mentioned device. The mixing ratio of the core material and the coating material (core material powder weight/coating material powder weight) can be used in the range of 0.1 to 50, but it can be adjusted in relation to the particle size ratio. preferable. When the particle size ratio is large, it is preferable to increase the mixing ratio, and when the particle size ratio is small, it is desirable to set the mixing ratio to 4 or less.
Simply reducing the mixing ratio does not necessarily improve the coating performance; in fact, in some cases, the larger the mixing ratio, the better the performance. Further, even if the mixing ratio is the same, the coating performance can be improved by dividing the coating agent powder into two or more parts and coating the powder several times. In any case, it is necessary that the coating material covers and adheres to the entire peripheral surface of the core material. This is because if the entire surrounding surface is not covered or adhered, the core substance inside will be eluted to the outside. <Effects of the Invention> The coated water-soluble vitamin formulation produced by the method of the present invention has significantly improved coating performance compared to conventionally known formulations, and as a result, contact with other ingredients can be prevented. Furthermore, it has become possible to block water-soluble vitamins from light, heat, moisture, and the outside air. Therefore, the effects of various water-soluble vitamins are not impaired when used in the fields of food and feed. Also, when the core substance is released to the outside,
Since it is released gradually, long-term effects can be expected. Furthermore, according to the method of the present invention, since the content of water-soluble vitamins in the preparation is increased, it is possible to reduce the amount of the preparation itself to be added, and therefore, it is possible to reduce the cost of using the preparation. Furthermore, the method for producing the preparation of the present invention can be simplified in terms of energy and workability compared to conventional production methods. As described above, the coated preparation of the present invention has many effects not seen before and is extremely useful. <Example> Reference example 1 Hydrogenated rapeseed oil (melting point
64.1°C, Nippon Oil & Fats Co., Ltd.) was added to 2 kg, and thoroughly dispersed using a homomixer. This mixture was sprayed into a room at 30°C using a rotating disk type sprayer to obtain a powder product. Reference Example 2 Nicotinic acid (average particle size
114 μm, manufactured by Givaudan) was added and thoroughly dispersed using a homomixer. A powder product was obtained by performing the same operation as in Reference Example 1. Reference example 3 Dissolved stearic acid monoglyceride (melting point
After adding 600 g of riboflavin (average particle size 146 μm, Nippon Rotsuyu Co., Ltd. product, trade name Robiflav) to 1.2 kg (64.7°C, manufactured by Riken Bitine Co., Ltd.), it was sufficiently dispersed with a homomixer. By performing the same operation as in Reference Example 1, a powder product having a particle size of 80 to 250 μm was obtained. Example 1 Thiamine nitrate (average particle size 124 μm, Nihon Rotsuyu Co., Ltd. product) 42 g and rapeseed hydrogenated oil (average particle size 8.6 μm,
Melting point 64.1°C, manufactured by Nippon Oil & Fats Co., Ltd.)) was placed in a centrifugal rotary mixer (Mechanomilu MM10, manufactured by Okada Seiko Co., Ltd.) together with 20 brass balls, and mixed for 4 hours at a rotational speed of 300 rpm. The obtained powder was mixed with the powder obtained in Reference Example 1 into minced anchovies at 10 mg/100 g as thiamine nitrate.
The decomposition rate of thiamine over time was investigated at 30°C. Thiamine was measured based on the Japanese Pharmacopoeia by adding a cyanogen bromide test solution to the extract and then measuring the absorbance at a wavelength of 368 nm.
【表】【table】
【表】
以上のように本発明による操作を実施すること
により硝酸チアミンの分解速度を大幅に低下させ
ることができた。
実施例 2
ニコチン酸(平均粒径114μm、ジボダン社製
品)160gとカルナウバワツクス(平均粒径8μ
m、融点83.57℃、野田ワツクス社製品、日本油
脂株式会社粉砕品)40gを粉体混合した後、奈良
ハイビリダイゼーシヨンシステム(株式会社奈良
機械製作所製)で5600r.p.m.で4分間処理した。
生成した粉末(ニコチン酸含量80%)を参考例2
(ニコチン酸含量40%)により製造した粉末と共
に溶出試験を行つた。溶出試験は生成した粉末を
ニコチン酸量0.3gに相当する量と水50mlとを三
角フラスコに入れ、恒温振とう器で毎分100回の
振とうを行い、水層に溶出したニコチン酸を水酸
化ナトリウム液で滴定し、定量した。表2に振と
う時間と溶出と溶出率の結果を締す(溶出率は、
全ニコチン酸量に対する溶出したニコチン酸の割
合をパーセントで表わしたものである)。[Table] By implementing the operation according to the present invention as described above, the decomposition rate of thiamine nitrate could be significantly reduced. Example 2 160 g of nicotinic acid (average particle size 114 μm, product of Givaudan) and carnauba wax (average particle size 8 μm)
After mixing 40 g of the powder (Noda Wax Co., Ltd. product, Nippon Oil & Fats Co., Ltd. pulverized product) with a melting point of 83.57°C, the mixture was treated with a Nara Hybridization System (manufactured by Nara Kikai Seisakusho Co., Ltd.) at 5600 rpm for 4 minutes.
The generated powder (nicotinic acid content 80%) was used as reference example 2.
(Nicotinic acid content: 40%). For the elution test, an amount of the generated powder equivalent to 0.3 g of nicotinic acid and 50 ml of water were placed in an Erlenmeyer flask, and the mixture was shaken 100 times per minute using a constant temperature shaker. The amount was determined by titration with a sodium oxide solution. Table 2 shows the results of shaking time, dissolution, and dissolution rate (dissolution rate is
(The ratio of eluted nicotinic acid to the total amount of nicotinic acid is expressed as a percentage).
【表】
この結果から本発明によればニコチン酸の含量
も高く、被覆性能もよい製品を作ることができる
が分かる。
実施例 3
参考例3により得られた粉末45gとステアリン
酸モノグリセライド微粉末(平均粒径17μm、融
点64.7℃、理研ビタミン社製、日本油脂社粉砕
品)5gと真ちゆう製のボール15個と共に遠心回
転型混合機(岡田精工社製、メカノミルー
MM10)に入れ、回転速度500r.p.m.で2時間反
応させた。得られた粉末を参考例3の粉末と共に
富山産業社製の自動溶出試験システムを用いて溶
出試験を行つた。溶出液にはPH7のリン酸緩衝溶
液を用い、波長は265nmで行つた。結果を表3に
示す。[Table] This result shows that according to the present invention, a product with a high nicotinic acid content and good coating performance can be produced. Example 3 45 g of the powder obtained in Reference Example 3, 5 g of stearic acid monoglyceride fine powder (average particle size 17 μm, melting point 64.7°C, manufactured by Riken Vitamin Co., Ltd., crushed product by NOF Corporation) and 15 balls made of brass were added. Centrifugal rotary mixer (manufactured by Okada Seiko Co., Ltd., Mechanomiru)
MM10) and reacted for 2 hours at a rotation speed of 500 rpm. The obtained powder was subjected to a dissolution test together with the powder of Reference Example 3 using an automatic dissolution test system manufactured by Toyama Sangyo Co., Ltd. A phosphate buffer solution of pH 7 was used as the eluent, and the wavelength was 265 nm. The results are shown in Table 3.
【表】
この結果から予備被覆を施こしたのみでは、被
覆が不十分である芯物質に本発明による被覆をす
ることにより大幅に性能を高めることができた。[Table] From these results, it was possible to significantly improve the performance by applying the coating according to the present invention to the core material, which was insufficiently coated only by applying a preliminary coating.
Claims (1)
点40℃以上の脂質粉状体を接触・衝突させ、上記
水溶性ビタミン類粉状体の全周囲表面に上記脂質
粉状体を付着・被覆し、水溶性ビタミン類を芯物
質として脂質が被覆された製剤を製造することを
特徴とする水溶性ビタミン類被覆製剤の製造方
法。 2 上記芯物質が常温で結晶状もしくは粉末状で
ある水溶性ビタミン類、又は水溶性成分、油性物
もしくは高分子物質により造粒もしくは予備被覆
された水溶性ビタミン類である特許請求の範囲第
1項に記載の被覆水溶性ビタミン類製剤の製造方
法。 3 芯物質と被覆剤との混合比(芯物質粉状体重
量/被覆剤粉状体重量)が0.1〜50である特許請
求の範囲第1項又は第2項に記載の水溶性ビタミ
ン類被覆製剤の製造方法。[Claims] 1. A water-soluble vitamin powder is brought into contact with and collided with a lipid powder having a melting point of 40°C or higher as a coating agent, and the lipid powder is coated on the entire circumferential surface of the water-soluble vitamin powder. 1. A method for producing a water-soluble vitamin-coated preparation, which comprises adhering and coating a water-soluble vitamin-coated preparation with a lipid-coated preparation using water-soluble vitamins as a core material. 2. Claim 1, wherein the core substance is water-soluble vitamins that are crystalline or powdery at room temperature, or water-soluble vitamins granulated or pre-coated with a water-soluble component, oily substance, or polymeric substance. The method for producing the coated water-soluble vitamin preparation described in Section 1. 3. The water-soluble vitamin coating according to claim 1 or 2, wherein the mixing ratio of the core material and the coating material (core material powder weight/coating material powder weight) is 0.1 to 50. Method of manufacturing the formulation.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61313550A JPS63164864A (en) | 1986-12-26 | 1986-12-26 | Production of coated preparation of water-soluble vitamin |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61313550A JPS63164864A (en) | 1986-12-26 | 1986-12-26 | Production of coated preparation of water-soluble vitamin |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS63164864A JPS63164864A (en) | 1988-07-08 |
JPH0358264B2 true JPH0358264B2 (en) | 1991-09-04 |
Family
ID=18042669
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP61313550A Granted JPS63164864A (en) | 1986-12-26 | 1986-12-26 | Production of coated preparation of water-soluble vitamin |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS63164864A (en) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH082248B2 (en) * | 1986-12-26 | 1996-01-17 | 日本油脂株式会社 | Method for producing coated organic acid and organic acid salt preparation |
JP2514201B2 (en) * | 1987-04-16 | 1996-07-10 | 横浜油脂工業株式会社 | Method for producing finely powdered L-ascorbic acid coating |
JP4147624B2 (en) * | 1998-06-03 | 2008-09-10 | 日油株式会社 | Method for producing powdery composition and powdery composition |
JP2001031590A (en) | 1999-04-05 | 2001-02-06 | Takeda Chem Ind Ltd | Production and use of coated preparation |
JP2001231470A (en) * | 2000-02-24 | 2001-08-28 | Taiyo Kagaku Co Ltd | Gel composition |
JP5157001B2 (en) * | 2005-04-30 | 2013-03-06 | ビーエイチエヌ株式会社 | Stabilized α-lipoic acid composition and use thereof |
JP4806969B2 (en) * | 2005-05-30 | 2011-11-02 | 日油株式会社 | Method for producing α-lipoic acid oil-coated powder and product thereof |
JP4703388B2 (en) * | 2005-12-06 | 2011-06-15 | 植田製油株式会社 | Thioctic acid composition and method for producing the same |
-
1986
- 1986-12-26 JP JP61313550A patent/JPS63164864A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS63164864A (en) | 1988-07-08 |
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