DK149482B - ADDITIONAL SUPPLEMENTS WHICH ARE ABLE TO PASS THE WAVE OF DRUGS, AND ITS USE FOR FEEDING OF DRUGS - Google Patents
ADDITIONAL SUPPLEMENTS WHICH ARE ABLE TO PASS THE WAVE OF DRUGS, AND ITS USE FOR FEEDING OF DRUGS Download PDFInfo
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- A—HUMAN NECESSITIES
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- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K40/00—Shaping or working-up of animal feeding-stuffs
- A23K40/30—Shaping or working-up of animal feeding-stuffs by encapsulating; by coating
- A23K40/35—Making capsules specially adapted for ruminants
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/10—Feeding-stuffs specially adapted for particular animals for ruminants
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Description
i 149482in 149482
Opfindelsen angår et mavepasserende fodertilskud til drøvtyggere i partikelform, ved hvilket 30-50 vægt% af i det mindste ét biologisk virksomt stof er forsynet med et overtræk, der indeholder en alifatisk monocarboxylsyre med 5 14 til 22 carbonatomer eller ricinolsyre eller en blan ding af flere af de nævnte syrerf samt anvendelsen af dette fodertilskud til fodring af drøvtyggere.The invention relates to a gastric feed supplement for ruminants in particulate form in which 30-50% by weight of at least one biologically active substance is provided with a coating containing an aliphatic monocarboxylic acid having 5 to 22 to 22 carbon atoms or ricinoleic acid or a mixture of several of said acid rf as well as the use of this feed supplement for feeding ruminants.
Fra DE-PS 22 12 568 kendes allerede et mavepasserende fodertilskud til drøvtyggere i partikelform, ved 10 hvilket mindst ét biologisk aktivt stof er forsynet mprj et overtræk, der er modstandsdygtigt over for omgivelsesbetingelserne i maven, men som efter passage ind i tarmen opløses under påvirkning fra galde og pankreassaft. Overtrækket består af en alifatisk monocarboxylsyre med 15 14 til 22 carbonatomer eller ricinolsyre eller en blan ding af sådanne syrer, eller er et salt af en sådan syre eller en blanding af sådanne syrer. Ved at opløsningen af overtrækket ved det kendte fodertilskud kræver påvirkning fra galde og pankreassaft, forkortes dog den 20 til fordøjelse og resorption til rådighed værende tid betragteligt.DE-PS 22 12 568 already discloses a gastric feeding supplement for ruminants in particulate form, at 10 of which at least one biologically active substance is provided with a coating which is resistant to the ambient conditions of the stomach, but which, after passage into the intestine, dissolves under influence. from bile and pancreatic juice. The coating consists of an aliphatic monocarboxylic acid having 15 to 22 carbon atoms or ricinoleic acid or a mixture of such acids, or is a salt of such an acid or a mixture of such acids. However, because the dissolution of the coating of the known feed supplement requires the influence of bile and pancreatic juice, the 20 available for digestion and resorption is considerably shortened.
Fodertilskuddet ifølge opfindelsen er kendetegnet ved, at overtrækket i forhold til totalvægten består af a) 10 til 35 vægt% af i det mindste ét natrium-, kalium- 25 eller calciumsalt af en alifatisk mo nocarboxylsyre med 14 til 22 carbonatomer eller ricinolsyre, b) resten op til 100 vægt%, dog mindst 30 vægt%Jaf mindst én alifatisk monocarboxylsyre 30 med 14 til 22 carbonatomer og/eller ricinolsyre og/eller et hærdet plante- eller dyrefedtstof.The feed supplement according to the invention is characterized in that the coating relative to the total weight consists of a) 10 to 35% by weight of at least one sodium, potassium or calcium salt of an aliphatic monocarboxylic acid having 14 to 22 carbon atoms or ricinoleic acid, b) the balance up to 100 wt.%, but at least 30 wt.% At least one aliphatic monocarboxylic acid 30 having 14 to 22 carbon atoms and / or ricinoleic acid and / or a hardened plant or animal fat.
Det har overraskende vist sig, at partiklerne af det omhandlede fodertilskud i modsætning til sådanne, 35 ved hvilke overtrækket enten kun består af fedtsyre el- 2 148482 ler kion af fedtsyresalte, angribes allerede i det sure miljø i løbemaven,og de biologisk aktive stoffer frigøres, uden at der kræves en yderligere påvirkning fra galde og pankreassaft. Men på den anden side modstår og-5 så partiklerne af den omhandlede fodertilskud et angreb fra et miljø med mavesafts pH og den mikrobielle nedbrydning i vommen.Som de efterfølgende eksempler viser, ligger den i mavemiljøet uopløste andel af fodertilskuddet ifølge opfindelsen i almindelighed noget højere end 10 ved de tilsvarende sammenligningsforsøg under anvendelse af de i eksemplerne beskrevne undersøgelsesbetingelser. Partiklerne af det omhandlede fodertilskud kan således passere vommen lige så godt som de fra DE-PS 22 12 568 kendte partikler, men begynder dog at blive opløst alle-15 rede i løbemaven, hvorved den til fordøjelse og resorption til rådighed værende tid forlænges.Surprisingly, it has been found that, unlike those in which the coating consists either of only fatty acid or of fatty acid salts, the particles of the feed supplement are already attacked in the acidic environment of the running stomach and the biologically active substances are released , without requiring any additional influence from bile and pancreatic juice. But on the other hand, the particles of the present feed supplement also withstand an attack from an environment of gastric juice pH and microbial degradation in the rumen. As the following examples show, the dissolved proportion of the feed supplement according to the invention is generally somewhat higher. than 10 in the corresponding comparison experiments using the test conditions described in the Examples. Thus, the particles of the present feed supplement can pass through the rumen as well as the particles known from DE-PS 22 12 568, but, however, begin to dissolve already in the running stomach, thereby extending the time available for digestion and resorption.
Fodertilskuddet ifølge opfindelsen består i forhold til totalvægten af 30 til 50 vægt% af mindst ét biologisk virksomt stof. Sådanne biologisk virksomme stof-20 fer er f.eks. aminosyrer, såsom methionin eller lysin; derivater af aminosyrer, såsom N-acylaminosyrer, f.eks. N-stearoylmethionin eller N-oleoylmethionin, calciumsaltet af N-hydroxymethylmethionin eller lysinmonohydro-chlorid; hydroxyanaloge forbindelser af aminosyrer, så-25 som 2-hydroxy-4-methylmercaptosmørsyre eller disses calciumsalte; proteiner, såsom fjerkræmel (Federmehl), fiskemel, casein eller kartoffelprotein; vitaminer, såsom vitamin A, vitamin A-acetat, vitamin A-palmitat, vitamin , vitamin E, nicotinsyre eller nicotinsyreamid, 30 calciumpanthotenat; (3-carotin; enzymer, såsom sure pro-teaser; carbohydrater, såsom glucose; veterinærfarmaceu-tika, f.eks. antibiotika, såsom chlortetracyclin, oxy-tetracyclin, chloramphenicol, zinkbacitracin; anthelmin-tika, såsom piperazinsalte; antiparasitika, såsom negu-3 5 von [(2,2,2,-trichlor-1-hydroxy-ethy1)-phosphorsyredi-methylester]. Der kan naturligvis også anvendes blandinger af to eller flere biologisk virksomme stoffer.The feed supplement according to the invention consists in relation to the total weight of 30 to 50% by weight of at least one biologically active substance. Such biologically active substances are e.g. amino acids such as methionine or lysine; derivatives of amino acids such as N-acylamino acids, e.g. N-stearoylmethionine or N-oleoylmethionine, the calcium salt of N-hydroxymethylmethionine or lysine monohydrochloride; hydroxy analogues of amino acids such as 2-hydroxy-4-methylmercapto butyric acid or their calcium salts; proteins such as poultry flour (Federmehl), fish meal, casein or potato protein; vitamins such as vitamin A, vitamin A acetate, vitamin A palmitate, vitamin, vitamin E, nicotinic acid or nicotinic amide, calcium panthotenate; (3-carotene; enzymes such as acidic proteases; carbohydrates such as glucose; veterinary pharmaceuticals, e.g. Of [(2,2,2, -trichloro-1-hydroxy-ethyl) -phosphoric acid methyl ester] Of course, mixtures of two or more biologically active substances can also be used.
Det overtræk, der beskytter de biologisk virksom- 149482 3 me stoffer i vommen,indeholder ligeledes i forhold til fodertilskuddets totalvægt 10 til 35 vægt% af mindst ét natrium-, kalium- eller calciumsalt af en alifatisk mono-carboxylsyre med 14 til 22 carbonatomer eller ricinolsyre 5 og til opfyldning op til 100 vægt%, dog i det mindste 30 vægt% i forhold til fodertilskuddets totalvægt af mindst en alifatisk monocarboxylsyre med 14 til 22 carbonatomer og/eller ricinolsyre og/eller et hærdet plante- eller dyrefedtstof, f.eks. hærdet sojabønneolie eller hærdet 10 oksetalg.The coating protecting the biologically active substances in the rumen also contains, in relation to the total weight of the feed supplement, 10 to 35% by weight of at least one sodium, potassium or calcium salt of an aliphatic monocarboxylic acid having 14 to 22 carbon atoms or ricinolic acid 5 and for filling up to 100% by weight, but at least 30% by weight relative to the total weight of the feed supplement of at least one aliphatic monocarboxylic acid having 14 to 22 carbon atoms and / or ricinolic acid and / or a cured plant or animal fat, e.g. . cured soybean oil or cured 10 beef tallow.
De i det beskyttende overtræk som frie fedtsyrer eller i form af natrium-, kalium- eller ealciumsalte foreliggende alifatiske monocarboxylsyrer med 14 til 22 carbonatomer kan være mættede eller umættede, forgrenede 15 eller ligekædede. De ligekædede i naturlige fedtstoffer forekommende fedtsyrer, såsom myristinsyre, palmitinsyre, stearinsyre, arachinsyre eller behensyre eller blandinger af sådanne syrer foretrækkes.The aliphatic monocarboxylic acids of 14 to 22 carbon atoms present in the protective coating as free fatty acids or in the form of sodium, potassium or alkaline salts can be saturated or unsaturated, branched or branched chain. The fatty acids present in natural fats, such as myristic acid, palmitic acid, stearic acid, arachic acid or behenic acid, or mixtures of such acids are preferred.
Fodertilskuddet ifølge opfindelsen kan hensigts-20 mæssigt fremstilles således, at først tilberedes en homogen smelte af de komponenter, der udgør det beskyttende overtræk. Derefter dispergeres det biologisk virksomme stof eller en blanding af sådanne stoffer, der skal beskyttes, under omrøring i denne smelte. Derefter føres 25 den flydende dispersion, der ved hjælp af vibrationer med høj frekvens, er sat i svingning gennem dyser. Derved opdeles den fra hver dyse udgående stråle i diskrete smådråber med defineret størrelse, der efter dannelse af en kugleform ved frit fald stivner. På denne måde kan 30 der fremstilles kugleformede partikler med et vilkårligt tværsnit mellem 50 og 2500 μπι.Conveniently, the feed supplement of the invention can be prepared such that first a homogeneous melt is prepared from the components that make up the protective coating. Thereafter, the biologically active substance or a mixture of such substances to be protected is dispersed with stirring in this melt. Then the liquid dispersion, which is vibrated through nozzles, is fed through high frequency vibrations. Thereby, the jet emanating from each nozzle is divided into discrete droplets of defined size which, after forming a spherical shape, solidify upon free fall. In this way, 30 spherical particles with any cross section between 50 and 2500 μπι can be produced.
Et i form af det omhandlede fodertilskud særligt vigtigt biologisk virksomt stof er methionin. Eftersom talrige undersøgelser viser, at blandt alle aminosyrer 35 er methionin i almindelighed den mest livsnødvendige a-minosyre for drøvtyggere. Således fører infusion af methionin i løbemaven hos får til en stigning i uldvæksten [P.J. Reis, P.G. Schinkel, Aust. J. Biol. Sci. 16, 218 4 149432 (1963)]. Hos holsteinske okser fører infuson af methio-nin i løbemaven til en forhøjet N-balance [C.R.Richardson, E.E.Hatfield, J. Anim. Sci. 4£, 740 (1978)]. Undersøgelser på lakterende køer er citeret af W. Kaufmann 5 og W. Lupping i "Z. Tierphysiol., Tierernåhrg. u. Futter-middelkde." 41, 202 (1979). Der er der også angivet resul-• tater af forsøg, der viser, at methionin, der er beskyttet under passagen af maven, hvor methioninen dog frigøres i løbemaven,som tilskud til en sædvanlig kraft-10 foderration hos malkekøer frembringer en stigning i mælkeydelsen,i protein- og fedtindholdet i mælken,i per-sistensen og i frugtbarheden efter begyndelsen af lakteringen.A particularly important biologically active substance in the form of the feed supplement is methionine. Since numerous studies show that of all amino acids 35, methionine is generally the most essential α-minoic acid for ruminants. Thus, infusion of methionine into the running stomach of sheep leads to an increase in wool growth [P.J. Reis, P.G. Schinkel, Aust. J. Biol. Sci. 16, 218 4 149432 (1963)]. In Holstein oxen, the infusion of methionine in the running stomach leads to an elevated N balance [C.R.Richardson, E.E.Hatfield, J. Anim. Sci. 4, 740 (1978)]. Studies on lactating cows are cited by W. Kaufmann 5 and W. Lupping in "Z. Tierphysiol., Tierernåhrg. U. Futter Middle Chain." 41, 202 (1979). Results of tests have also been reported showing that methionine protected during the passage of the stomach, whereby the methionine is released into the running stomach, as a supplement to the usual force-feeding ration in dairy cows produces an increase in milk yield. in the protein and fat content of the milk, in the persistence and in the fertility after the onset of lactation.
Opfindelsen angår endvidere anvendelsen af det om-handlede fodertilskud, i en daglig dosis fra 1 til 100 g, til fodring af drøvtyggere.The invention further relates to the use of the present feed supplement, at a daily dose of from 1 to 100 g, for feeding ruminants.
Fodertilskuddet ifølge opfindelsen anvendes fortrinsvis med methionin som biologisk virksomt stof og i-sær til fodring af malkekøer, til forbedring af mælkeydelsen, 20 protein- og fedtindholdet i mælken, persistensen og/eller frugtbarheden efter begyndelsen af lakteringen.The feed supplement of the invention is preferably used with methionine as a biologically active substance and especially for feeding dairy cows, to improve milk yield, protein and fat content of milk, persistence and / or fertility after the beginning of lactation.
Andre vigtige biologisk virksomme forbindelser er vitaminerne. Således fører f.eks. vitamin-A-mangel hos okser til dårlig appetit og derfor til ringe vægtforøgel-25 se. Hos drægtige køer kan det forårsage kalvekastning eller dødfødte kalve. β-Carotin har en specifik virkning på oksers frugtbarhed [Dt. Tierårztl. Wschr. J32, 444 (1975)].Other important biologically active compounds are the vitamins. Thus, e.g. Vitamin A deficiency in bulls for poor appetite and therefore for poor weight gain. In pregnant cows it can cause calf throwing or stillborn calves. β-Carotene has a specific effect on the fertility of oxen [Dt. Tierårztl. Wschr. J32, 444 (1975)].
En energetisk underernæring af højtydende dyr kan ^ føre til forringet mælkeproteinydelse. Tilføring af car-hohydrater, såsom glucose, i beskyttet form fører herved til en særdeles gunstig energitilføring.Energetic malnutrition of high-performance animals can lead to impaired milk protein performance. Addition of carbohydrates, such as glucose, in protected form thereby leads to a very favorable energy supply.
Ved oralt indgivne medikamenter ønskes i almindelighed en frigørelse af det aktive stof først efter pas-35 sage af maven. Det omhandlede fodertilskud er da særligt egnet, såfremt der ønskes en frigørelse i løbemaven.In the case of orally administered drugs, a release of the active substance is generally desired only after passage of the stomach. The feed supplement in question is then particularly suitable if a release in the running stomach is desired.
149482 5149482 5
Opfindelsen belyses nærmere ved de efterfølgende eksempler og sammenligningsforsøg. Såfremt andet ikke er angivet, betyder dele vægtdele og procenter vægtprocenter.The invention is further illustrated by the following examples and comparative experiments. Unless otherwise stated, parts represent parts by weight and percentages by weight.
Eksempel 1 5 a) (Sammenligningsforsøg).70 dele stearinsyre smel tedes ved 80°C. 30 Dele methionin suspenderedes under omrøring,og smelten blev dryppet ud fra dyser, hvorved aer fremkom ensartede kugleformede partikler med tværsnit på 1 til 2 mm.Example 1 a) (Comparative Experiment) .70 parts of stearic acid were melted at 80 ° C. 30 parts of methionine were suspended with stirring and the melt was dripped from nozzles to give uniform spherical particles with a cross section of 1 to 2 mm.
10 b) Ud fra en blanding af 60 dele stearinsyre og 10 dele natriumstearat blev der ved opvarmning til 80°C fremstillet en homogen smelte, hvori der ligeledes blev indrørt 30 dele methionin. Fremstillingen af partiklerne skete som ved a).B) From a mixture of 60 parts of stearic acid and 10 parts of sodium stearate, upon heating to 80 ° C, a homogeneous melt was prepared in which 30 parts of methionine were also stirred. The particles were prepared as in (a).
15 På analog måde fremstilledes partikler af: c) 30 dele methionin, 55 dele stearinsyre og 15 dele natriums te arat, d) 30 dele methionin, 50 dele stearinsyre og 20 dele natri vims tearat , 20 e) 30 dele methionin, 50 dele stearinsyre og 20 dele kaliums tearat, f) 30 dele methionin, 45 dele stearinsyre og 25 dele natriums tear at , g) 30 dele methionin, 35 dele stearinsyre og 35 dele na- 25 triumstearat.By analogy, particles were prepared from: c) 30 parts of methionine, 55 parts of stearic acid and 15 parts of sodium tea arate, d) 30 parts of methionine, 50 parts of stearic acid and 20 parts of sodium tearate, 20 e) 30 parts of methionine, 50 parts of stearic acid and 20 parts potassium tearate, f) 30 parts methionine, 45 parts stearic acid and 25 parts sodium tear, g) 30 parts methionine, 35 parts stearic acid and 35 parts sodium stearate.
Til vindersøge Ise af den specifikke pH-afhængige fri* gørelse under udnyttelse af pH-forskellen mellem mavesaft og løbemavesaft blev partiklerne inkuberet i et rysteapparatur i hvert tilfælde i 2 timer ved 37°C i 50 ml 30 af et puffersystem, der pH-mæssigt svarede til mavemil-jøet og under stadig bevægelse. Puffersystemet bestod af en opløsning af 74,77 g kaliumdihydrogenphosphat, 103,03 g dinatriumhydrogenphosphattrihydrat og 13,5 g kaliumiodid i 1 liter vand. Puffersysternets pH-værdi var 149482 6 6,5. Samtidig blev partiklerne inkuberet i 2 timer ved 37°C i 50 ml puffersystem, der pH-mæssigt svarede til løbemavemiljøet. Dette system bestod af en opløsning af 6,5 ml 0,2 N saltsyre og 25,0 ml 0,2 N kaliumchloridop-5 løsning i 100 ml vand. Dette puffersystems pH-værdi var 2,0.To find the specific pH-dependent release using the pH difference between gastric juice and running gastric juice, the particles were incubated in a shaker in each case for 2 hours at 37 ° C in 50 ml of a buffered pH system. corresponded to the stomach mildew and still moving. The buffer system consisted of a solution of 74.77 g of potassium dihydrogen phosphate, 103.03 g of disodium hydrogen phosphate trihydrate and 13.5 g of potassium iodide in 1 liter of water. The pH of the buffer system was 6.5. At the same time, the particles were incubated for 2 hours at 37 ° C in 50 ml of buffer system that was pH-equivalent to the running stomach environment. This system consisted of a solution of 6.5 ml of 0.2 N hydrochloric acid and 25.0 ml of 0.2 N potassium chloride solution in 100 ml of water. The pH of this buffer system was 2.0.
Derefter affiltreredes de ikke opløste partikler og opløsningen i hvert tilfælde tilsat 100 ml phosphat-puffer med pH 6,5, hvorved der i hvert tilfælde resul-10 terede en pH-værdi på 6,5. Andelen af det fra partiklerne i opløsning overgåede methionin blev derpå bestemt iodometrisk.Then, the dissolved particles were filtered off and the solution in each case added 100 ml of pH 6.5 phosphate buffer, resulting in a pH of 6.5 in each case. The proportion of the methionine transferred from the particles in solution was then determined iodometrically.
Resultaterne er anført i den følgende tabel 1.The results are given in the following Table 1.
149482 7 dø P (1)149482 7 die P (1)
•H <H• H <H
m G O •Η Λ β Φ r·· σι σι ro in oo vo 0t> τΐίιΐ ,β g ffl β\ ¢0 rl (Ί ΙΟ ·Φ •ρ φ 0) Λ s s ιΗ α>___ τ3 --- G Ρ Π) Φ U-ι to 'ί 1ί) Η t' (Ν Ιίΐ 4J <4-1 *. s ». ·· ν ·* ^ m3 σι ro ιη νο ιη αο γ~ φ (¼ co eo oo oo oo οο .-) φ 04 >m GO • Η Λ β Φ r ·· σι σι ro in oo vo 0t> τΐίιΐ, β g ffl β \ ¢ 0 rl (Ί ΙΟ · Φ • ρ φ 0) Λ ss ιΗ α> ___ τ3 --- G Ρ Π) Φ U-ι to 'ί 1ί) Η t' (Ν Ιίΐ 4J <4-1 *. S ». ·· ν · * ^ m3 σι ro ιη νο ιη αο γ ~ φ (¼ co eo oo oo oo οο .-) φ 04>
Ο m D SΟ m D S
r-H ....... 1 1 * pH -·—' " -—«» ^ φ -Ρ tf <0 (ti ^-ν Φ <0 Λ π3 3 3 3 « Ζ !3 (d Ρ _ μ -Pm ΦΦ omoomm +)+) I η η cm cs cm ηrH ....... 1 1 * pH - · - '"-—« »^ φ -Ρ tf <0 (ti ^ -ν Φ <0 Λ π3 3 3 3« Ζ! 3 (d Ρ _ µ -Pm ΦΦ omoomm +) +) I η η cm cs cm η
XrJi 0_____ Ό ο Φ Ρ Μ CU>i ίαXrJi 0_____ Ό ο Φ Ρ U CU> i ία
Ρ GΡ G
Φ·Η οοηοοηιη Μ ΐ' « ιη λ λ μ tnm G Φ •Η-Ρ G in p (g--σι ω G ’S· G Ή ΜΦ · Η οοηοοηιη Μ ΐ '«ιη λ λ μ tnm G Φ • Η-Ρ G in p (g - σι ω G' S · G Ή Μ
Φ G PΦ G P
go o g -ri OOOOOOO 4-1 id r· n m m ro m ro m to co+> O'go o g -ri OOOOOOO 4-1 id r · n m m ro m ro m to co +> O '
Φ GΦ G
S -HS -H
GG
__________________ Cn__________________ Cn
•H• H
f“lf "l
GG
Cn W g w ΐ S ”o m ai ίί o i p lu 0 i—JrHrHrHrHrHrH C/} ,_fe____ * 149482 8Cn W g w ΐ S ”o m ai ίί o i p lu 0 i — JrHrHrHrHrHrH C /}, _fe ____ * 149482 8
Produktet med en stearatandel på 20% viser en meget vidtgående frigørelse af methionin ved pH-forhol-dene i løbemaven, uden at enzymatisk aktivitet var nødvendig. En mindre eller større stearatandel fører til en 5 mindre effektiv frigørelse af methionin under inkubationstiden på kun 2 timer.The 20% stearate product shows a very wide release of methionine at pH conditions in the running stomach without enzymatic activity being required. A smaller or greater proportion of stearate leads to a less efficient release of methionine during the incubation time of only 2 hours.
Denne virkning kan også ses med øjnene. Mens partiklerne ifølge a) efter inkubation i den sure puffer ikke viste nogen ydre ændring, var partiklerne ifølge 10 d) og e) revnet adskillige steder. Partiklerne ifølge b), f) og g) viste en ringe opblødning af det ydre lag.This effect can also be seen with the eyes. While the particles of a) after incubation in the acidic buffer showed no external change, the particles of 10 d) and e) were cracked in several places. The particles of b), f) and g) showed a slight softening of the outer layer.
Eksempel 2 På tilsvarende vis blev der fremstillet partikler med en nethioninandel på 40% i forhold til slutproduktet.Example 2 Similarly, particles having a net hionine content of 40% relative to the final product were prepared.
15 Natriumstearatandelen blev indstillet på 10, 15 og 20%.The sodium stearate fraction was adjusted to 10, 15 and 20%.
Til sammenligning blev der fremstillet og undersøgt et produkt uden stearattilsætning.In comparison, a product without stearate addition was manufactured and tested.
Sammensætningen og resultaterne er anført i tabel 2.The composition and results are listed in Table 2.
149482 9 <*> μ149482 9 <*> µ
<D<D
-Hm 44 P P •H ft p q) ο > Η Π H σι •H id - - ' *· ο! Ξ m οι σι a\ -P <u σι σι ^ n ΟΛ e «.-Hm 44 P P • H ft p q) ο> Η Π H σι • H id - - '* · ο! Ξ m οι σι a \ -P <u σι σι ^ n ΟΛ e «.
PIPI
HH
Q)__ 'dQ) __ 'd
S MS M
id <uid <u
M-ι r~ >o οι HM-ι r ~> o οι H
4-1 Ή *« *· *· *· in p ri m co4-1 Ή * «* · * · * · in p ri m co
•Q. ft h CO CO OO• Q. ft h CO CO OO
H a) ft> 04 0 id H __ Q) -—- -—- ,q 4-1 id id id id id 2 2 3H a) ft> 04 0 id H __ Q) -—- -—-, q 4-1 id id id id id 2 2 3
Eh S4 w w id (D o in oEh S4 w w id {D o in o
+) 44 I Η H CM+) 44 I Η H CM
a) ω 44 44 P--a) ω 44 44 P--
Ό <UΌ <U
0 M0 M
>4 >1 ft to p ιμ -Η ο o in ο id 5η νο m ^ 'a* <d Cn <D P +> H 05 5 —_ U> « -a w p w p -η u a> p o so ή 1 ·Η ο ο ο Ο 01 3 ο! vf <ί ^ vf Φ 05 4J ρ a) ή S & cn _ Ή f—j Ρ σ< » ο W id Λ 0 Ό 1 Μ 3 0 04 ΟΙ ΟΙ ΟΙ 05 la _ Μ 149482 10> 4> 1 ft to p ιμ -Η ο o in ο id 5η νο m ^ 'a * <d Cn <DP +> H 05 5 —_ U> «-awpwp -η ua> po so ή 1 · Η ο ο ο Ο 01 3 ο! vf <ί ^ vf Φ 05 4J ρ a) ή S & cn _ Ή f — j Ρ σ <»ο W id Λ 0 Ό 1 Μ 3 0 04 ΟΙ ΟΙ ΟΙ 05 la _ Μ 149482 10
En større stearatandel som beskrevet i eksemplerne fører til en forøgelse af smeltens viskositet, således at fremstillingen også af større partikler besværliggøres. Ved en fuldstændig erstatning af.fedtsyren med 5 et salt af fedtsyren kan en smelte ikke fremstilles, ej heller ved anvendelse af temperaturer på 180°C. Dette fører endvidere til en væsentlig større termisk belastning af stoffet, der skal beskyttes.A larger proportion of stearate as described in the examples leads to an increase in the viscosity of the melt, so that the preparation of larger particles is also complicated. By completely replacing the fatty acid with a salt of the fatty acid, a melt cannot be prepared, even using temperatures of 180 ° C. This also leads to a significantly greater thermal load on the fabric to be protected.
Eksempel 3 10 Til sammenligning af de ovenfor beskrevne under søgelser med resultater ved anvendelse af fysiologiske opløsninger inkuberes produktet efter forsøg 1 d) med 50 ml løbemavesaft opnået fra frisk slagtede okser ligeledes ved 37°C i 2 timer. Bestemmelsen skete på samme 15 måde. Resultatet er vist i tabel 3.Example 3 For comparison of the above-described tests with results using physiological solutions, the product, after Experiment 1 d), is incubated with 50 ml of running stomach juice obtained from freshly slaughtered oxen at 37 ° C for 2 hours. The determination happened in the same way. The result is shown in Table 3.
149482 11 +> d? m <o149482 11 +> d? m <o
ri COri CO
O) CNO) CN
G > •H (0 vo g s oi O 0) •Η Λ Λ «ι +> P5 I_— rH 0)G> • H (0 vo g s oi O 0) • Η Λ Λ «ι +> P5 I_— rH 0)
O) VH fd M-JO) VH fd M-J
g 3 3ft cng 3 3ft cn
CDCD
-P > VO-P> VO
to 3 Hto 3 H
«V S r-» a) ft Λ O -Sv D PI«V S r-» a) ft Λ O -Sv D PI
n H »-* φ +> 3 λ nj a (0 H w fri (0 tu on H »- * φ +> 3 λ nj a (0 H w free (0 tu o
+)+) <N+) +) <N
<u m +> fd φ 0 in u >t ft ω<u m +> fd φ 0 in u> t ft ω
GG
m -a o to M in 3 tn a) G +> •Htflm -a o to M in 3 tn a) G +> • Htfl
GG
+>__+> __
fBfB
to G G -H Ο) Gto G G -H Ο) G
1 o E -Η o 3 Λ to W +J 0) a O) εη o •s to — ^ M 3 Λ1 o E -Η o 3 Λ to W + J 0) a O) εη o • s to - ^ M 3 Λ
OISLAND
fa n 149482fa n 149482
Eksempel 4 12Example 4 12
Til bedømmelse af, om der med det efter forsøg 1 b) opnåede produkt med en natriumstearatandel på 10% også ved længere inkubation i løbemavesaft kan iagttages 5 en forøget frigørelse i forhold til produktet efter forsøg 1 a) (uden stearatandel), blev begge produkterne hver inkuberet i 16 timer ved 37°C i løbemavesaft. Derved fremkaa de de følgende resultater (tabel 4).To assess whether the product obtained after Experiment 1 b) with a sodium stearate content of 10% can also be observed by prolonged incubation in running gastric juice 5 an increased release compared to the product after Experiment 1 a) (without stearate proportion), both products were each incubated for 16 hours at 37 ° C in running gastric juice. In doing so, they presented the following results (Table 4).
dPdP
•Η P• Η P
<D fi S<D fi S
•ri -ri• ri -ri
β -P Oβ -P O
•ri 40• ri 40
-5H-5
e Ή r- ro ι-i (ύ - * Φ t n n in Ό d) Γ" CM fi >e Ή r- ro ι-i (ύ - * Φ t n n in Ό d) Γ "CM fi>
(tf (tf , S(tf (tf, S
+J φ tn Λ H J ft'—+ J φ tn Λ H J ft'—
OISLAND
DD
iH __ r-T" φ +> (tf Λ- , <tf 2 (tf +» P ~ E-t 0) (tf +> Φ o X +> I Ή β W Ό O —- P Φ ftpiH __ r-T "φ +> (tf Λ-, <tf 2 (tf +» P ~ E-t 0) (tf +> Φ o X +> I Ή β W Ό O —- P Φ ftp
m tn (tf β •Hm tn (tf β • H
O' P o oO 'P o o
β (tf t- UDβ (tf t- UD
-ri φ · β +1 04 +> to -a æ tn in —- p β β Ο Φ ·Η <Η S β ιη go tn (tf -Η Ο Ο β οι Λ η η ·Η +> β Φ 04 --β 04 * Φ-ri φ · β +1 04 +> to -a æ tn in —- p β β Ο Φ · Η <Η S β ιη go tn (tf -Η Ο Ο β οι Λ η η · Η +> β Φ 04 --β 04 * Φ
tn "(tf Λ Stn "(tf Λ S
ρ ίο 0 t Ί1 01 fa _ * 149482 13ρ ίο 0 t Ί1 01 fa _ * 149482 13
Eksempel 5 På tilsvarende vis som i eksempel 1 og 2 fremstilledes et produkt bestående af a) 30% lysinhydrachlorid og 70% stearinsyre samt b) 30% lysinhydrochlorid, 50% 5 stearinsyre og 20% natriumstearat.Example 5 In a similar manner to Examples 1 and 2, a product of a) 30% lysine hydrochloride and 70% stearic acid was prepared, and b) 30% lysine hydrochloride, 50% stearic acid and 20% sodium stearate.
Efter inkubation i løbemavepuffer i 2 timer ved 37°C affiltreredes partiklerne, og opløsningerne blev undersøgt søjlechromatografisk på aminosyreanalysatoren LKB 3201 for lysinindholdet.After incubation in running stomach buffer for 2 hours at 37 ° C, the particles were filtered off and the solutions were column-chromatographically examined on the amino acid analyzer LKB 3201 for the lysine content.
10 Derved fandtes de følgende forskelle i frigø relseshastigheden (tabel 5).10 Thereby, the following differences were found in the release rate (Table 5).
149482 14 dp149482 14 dp
HMHM
<u T3 g •P -P P +» 0 H CN Λ 0 - Ο P P Q)<u T3 g • P -P P + »0 H CN Λ 0 - Ο P P Q)
Ό ip i-( OΌ ip i- (O
>i4H ' ^> i4H '^
Λ 3 P* <NΛ 3 P * <N
β Q. t" (Nβ Q. t "(N
•h a) w > >1 (0 Ή S a) Η Λ (!) ·& T3 P] β-" β• h a) w>> 1 (0 Ή S a) Η Λ (!) · & T3 P] β- "β
-P-P
in s 1-1 in a» 0in s 1-1 in a »0
H DH D
a)--— J3 -P βa) - - J3 -P β
Kj -p (0 s B O) P -- -P (0Kj -p (0 s B O) P - -P (0
ϋ (D Oϋ (D O
3 -P I nj 'd w 0 p__ a--3 -P I nj 'd w 0 p__ a--
<D<D
Ή p β >t 0) O' β β ·Η Ο Ο •HP r- ρ* β β +ι 0) (Β *Ρ tn cn β Ο) οι 1 ---ο.Ή p β> t 0) O 'β β · Η Ο Ο • HP r- ρ * β β + ι 0) (Β * Ρ tn cn β Ο) οι 1 --- ο.
εη ω <3 υ Ρ w ® ο ο ο ή • mm ω Οι m β t*i ·Ρ Ρ! β θ' Ήεη ω <3 υ Ρ w ® ο ο ο ή • mm ω Οι m β t * i · Ρ Ρ! β θ 'Ή
r—Ir-In
θ' λ β -& Ο) W β Λ 6θ 'λ β - & Ο) W β Λ 6
Ρ SΡ S
0 in in β0 in β
IP CQIP CQ
___ *·___ * ·
Eksempel 6 149482 15Example 6
Svarende til eksempel 1 blev der fremstillet partikler af a) 30% nicotinsyreamid og 70% stearinsyre samt b) 30% nicotinsyreamid, 50% stearinsyre og 20% natrium-5 stearat.In accordance with Example 1, particles of a) 30% nicotinic acid amide and 70% stearic acid were prepared, and b) 30% nicotinic acid amide, 50% stearic acid and 20% sodium stearate.
Efter inkubation i løbemavesaft i 2 timer ved 37°C blev partiklerne affiltreret og N-indholdet bestemt ved Kjeldahl-metoden. Ved sammenligning med det inden inkubationen analyserede N-indhold fastlagdes frigørel-10 sens, udstrækning. Resultatet er vist i tabel 6. .After incubation in running gastric juice for 2 hours at 37 ° C, the particles were filtered off and the N content determined by the Kjeldahl method. By comparison with the N content analyzed before the incubation, the extent of release was determined. The result is shown in Table 6..
———---
•H• H
d •ri Φ Φ μ sd • ri Φ Φ µ s
>l*rl M -P S> l * rl M -P S
•rH CM +> Ο ·* ϋ μ •μ φ fim Η η m - * rH fi σι Ο Οι Ό Φ ΰ > td id , ε -Ρ φ ι»Λ Η ι-3 Ό ft—' Ο• rH CM +> Ο · ϋ µ • µ φ fim Η η m - * rH fi σι Ο Οι Ό Φ ΰ> td id, ε -Ρ φ ι »Λ Η ι-3 Ό ft— 'Ο
Η DΗ D
Φ — .. - Λ ««% id +> ΦΦ - .. - Λ ««% id +> Φ
Eh Φ I 3 -Ρ fd — Μ Φ +> fi 4-) id ο τΙ οι Ρ ι cm ο μ.,. -Eh Φ I 3 -Ρ fd - Μ Φ +> fi 4-) id ο τΙ οι Ρ ι cm ο μ.,. -
ft Ift I
s m ·μ id Μ id φ tji® μ ο ο οι C 4-1 >1 r* in Ό.s m · μ id Μ id φ tji® μ ο ο οι C 4-1> 1 r * in Ό.
-μ οι in to Α μ +j——- ο (Β ι φ m οι fi -μ ω C3 Ή fi Ο· Φ 4-1 id Ο Ο fi f o Φ ro η ·μ Ο μ fi id ·μ >ι 0> ca 2 οι ·μ Η "Π—ι- c ΰ> * φ Ό π Φ Id λ 1 μ id Ο « Φ 01 ,Ja__#-µ οι in to Α μ + j ——- ο (Β ι φ m οι fi -μ ω C3 Ή fi Ο · Φ 4-1 id Ο Ο fi fo Φ ro η · μ Ο μ fi id · μ> ι 0> ca 2 οι · μ Η "Π — ι- c ΰ> * φ Ό π Φ Id λ 1 μ id Ο" Φ 01, Yes __ #
Eksempel 7 149482 16 På tilsvarende vis som i eksempel 1 og 2 blev der fremstillet partikler, ved hvilke der i det beskyttende lag blev anvendt hærdet sojaolie.Example 7 Particles were prepared in a similar manner to Examples 1 and 2 using hardened soybean oil in the protective layer.
5 Sammensætningen og resultatet af den som i eksem pel 1 gennemførte undersøgelse er vist i tabel 7.5 The composition and results of the study as in Example 1 are shown in Table 7.
u dP d)u dP d)
Ή -H IHΉ -H IH
3 C ft -H <s) vo σ> r- β > *· - *· 0(d -s· f'· σι •Hg σ\ m3 C ft -H <s) vo σ> r- β> * · - * · 0 (d -s · f '· σι • Hg σ \ m
X <D -p X Φ e· g XX <D -p X Φ e · g X
HH
<D~ -- Ό β U (C d) ih +> m i" o o *H ia 3 · ^ · 0) a & vo σι X Η φ σ σ vo X ft ><D ~ - Ό β U (C d) ih +> m i "o o * H ia 3 · ^ · 0) a & vo σι X Η φ σ σ vo X ft>
Ed O 3 s aEd O 3 s a
P -PP -P
tin ~ +»y w « X 3 w — 3 0) Ό -P o otin ~ + »y w« X 3 w - 3 0) Ό -P o o
O 01 I H CMO 01 I H CM
MM
ft- - 0)ft- - 0)
Ή ·Η Id -P Η O OΉ · Η Id -P Η O O
&i'U id o o o fi Η ·η Is id ifl ¢1 •H fB O -a β S U ΙΑ Ρ, Μ «73 0 w ·η m β β ΙΑ ο ο σι Β ·η ο ο ο g g X η η η ·η id -Ρ β οι φ σι a ·η ________ Η _ β σ> ο& i'U id ooo fi Η · η Is id ifl ¢ 1 • H fB O -a β SU ΙΑ Ρ, Μ «73 0 w · η m β β ΙΑ ο ο σι Β · η ο ο ο gg X η η η · Η id −Ρ β οι φ σι a · η ________ Η _ β σ> ο
a * Ia * I
Μ ΐ Λ Ο IΟ ΐ Λ Ο I
Ρ 'οι ϋι f» Ρ. Κ U9482 17Ρ 'οι ϋι f »Ρ. Κ U9482 17
Eksempel 8 På tilsvarende vis som beskrevet ovenfor blev der fremstillet produkter, ved hvilke methionin og protein i kombination beskyttedes. Som protein blev der anvendt 5 fjerkræmel (Federmehl).Example 8 Similarly, as described above, products were prepared in which methionine and protein in combination were protected. As a protein, 5 poultry flour (Federmehl) was used.
Efter gennemføring af inkubationen i mave- og lø-bemavepuffer som i eksempel 1 blev opløsningerne undersøgt søjlechromatografisk for aminosyreindholdet. Ud over methionin kunne andre aminosyrer kun eftervises i spor-10 mængder.After conducting the incubation in gastric and placebo buffer as in Example 1, the solutions were examined column chromatographically for the amino acid content. In addition to methionine, other amino acids could only be detected in trace-10 amounts.
Sammensætningen og resultatet er vist i tabel 8.The composition and result are shown in Table 8.
Eksempel 9 a) {Sammenligningsforsøg) 70 dele stearinsyre blev smeltet ved 80°C. 30 dele methionin suspenderedes deri under omrøring, og smelten blev dryppet ud fra dyser, hvorved der fremkom ensartede kugleformede partikler med tværsnit på 1 til 2 mm.Example 9 a) {Comparative Experiment) 70 parts of stearic acid were melted at 80 ° C. Thirty parts of methionine were suspended therein with stirring and the melt was dripped from nozzles to give uniform spherical particles of 1 to 2 mm cross-section.
b) Ud fra en blanding af 60 dele stearinsyre og 10 dele calciumstearat blev der ved opvarmning til 80°C fremstil- 20 let en homogen smelte, hvori der ligeledes blev suspenderet 30 dele methionin. Smelten blev dryppet ud fra dyser, hvorved der fremkom ensartede kugleformede partikler med en diameter på 1 til 2 mm.b) From a mixture of 60 parts of stearic acid and 10 parts of calcium stearate, upon heating to 80 ° C a homogeneous melt was prepared in which 30 parts of methionine were also suspended. The melt was dripped from nozzles to produce uniform spherical particles with a diameter of 1 to 2 mm.
På samme måde fremstilledes partikler ud fra: 25 c) 30 dele methionin, 50 dele stearinsyre og 20 dele calciumstearat, d) 30 dele methionin, 35 dele stearinsyre og 35 dele calciumstearat.Similarly, particles were prepared from: 25 c) 30 parts methionine, 50 parts stearic acid and 20 parts calcium stearate, d) 30 parts methionine, 35 parts stearic acid and 35 parts calcium stearate.
De fremstillede partikler blev hver gang undersøgt 30 på den i eksempel 1 beskrevne måde. Resultaterne er vist i den efterfølgende tabel 9.The particles prepared were examined each time in the manner described in Example 1. The results are shown in the following Table 9.
149482 18 η -- o Ή ϋ9 U Ή α) d Η ή ρ, r~ m ιο co IH α) - *. ·. » s3 ί c*p > to tn ro γί Ο ft θ' (Ί (0 m a ^ a β α) - - - -Hg . ο > m oo co μ <d 5S " g S' U ^149482 18 η - o Ή ϋ9 U Ή α) d Η ή ρ, r ~ m ιο co IH α) - *. ·. »S3 ί c * p> to tn ro γί Ο ft θ '(Ί (0 m a ^ a β α) - - - -Hg. Ο> m oo co µ <d 5S" g S' U ^
s3 Is3 I
ω—-- 5 S3 in I——I-ω —-- 5 S3 in I —— I-
(3 (U B(3)
W n, +) ih r- ^ vo ^ to β - « * Ό. & o σι i i.W n, +) ih r- ^ vo ^ to β - «* Ό. & o σι i i.
H g VS) VD t- φ Q) S' s Ό «ΗH g VS) VD t- φ Q) S 's Ό «Η
2 $ β *H2 $ β * H
3¾ (¾ D CO OJ VD CD3¾ (¾ D CO OJ VD CD
— — —. O J ·. «. » -«· . +) <d σ\ <-t in vs η 0 7? to > r- co oo as 2 S S 5l » S „ §-s 4J o o 2 H CO I i—I ΓΊ _j ^ ® <u -- Λ ---,£) JJ ^ „ 2nu 2 « β β β 64 e & B J3 , ϋ u o -P co ® I ~ ~ ^ ,Μ β Ο Ο Ο ^ ® αοιη 3Ή m vf η . *i >5 ^ ·ημ r~> cm m p (3 --- MO) rtl- - -. O J ·. '. »-« ·. +) <d σ \ <-t in vs η 0 7? to> r- co oo as 2 SS 5l »S„ §-s 4J oo 2 H CO I i — I ΓΊ _j ^ ® <u - Λ ---, £) JJ ^ „2nu 2« β β β 64 e & B J3, ϋ uo -P co ® I ~ ~ ^, Μ β Ο Ο Ο ^ ® αοιη 3Ή m vf η. * i> 5 ^ · ηµ r ~> cm m p (3 --- MO) rtl
ft+> Sft +> S
to z m 73 <u o & 5 S' 8 g ,|j I ft -Η Ο Ο O in 3H ΗΓ'-νοιηη -PA! O O O 3J Π5 RJ H m <N cn "’α» tn M Q) fr, +> «.to z m 73 <u o & 5 S '8 g, | j I ft -Η Ο Ο O in 3H ΗΓ'-νοιηη -PA! O O O 3J Π5 RJ H m <N cn "'α» tn M Q) fr, +> «.
β-η · S1 W Wβ-η · S1 W W
gft § -H___ Mgft § -H ___ M
« ^ r1 n g - CO R C £ Φ fi M cu *H (/} CQ *H O S C £ β Ή 2 ο « Q to ϊί·Ηθσοο .j •hooo 0) e-β m m m m g jincnnG g -Ρ &«^ R1 n g - CO R C £ Φ fi M cu * H (/} CQ * H O S C £ β Ή 2 ο« Q to ϊί · Ηθσοο .j • hooo 0) e-β m m m m g jincnnG g -Ρ &
•P -H S 0) -H• P -H S 0) -H
3 & m 2 H3 & m 2 H
- —-- 3 Γ 0)- —-- 3 Γ 0)
0» * fig, I0 »* fig, I
to ΒΛΟ § g ---— — COtwo ΒΛΟ § g ---— - CO
M 5 H S 32 U 73 0 CO 00 OO 55 g ft tO ? 3 3 31 *M 5 H S 32 U 73 0 CO 00 OO 55 g ft tO? 3 3 31 *
Applications Claiming Priority (2)
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DE3013000A DE3013000C2 (en) | 1980-04-03 | 1980-04-03 | Rumen penetrating feed additive for ruminants and its use for feeding ruminants |
DE3013000 | 1980-04-03 |
Publications (3)
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DK131381A DK131381A (en) | 1981-10-04 |
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DK149482C DK149482C (en) | 1986-12-08 |
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DK131381A DK149482C (en) | 1980-04-03 | 1981-03-23 | ADDITIONAL SUPPLEMENTS WHICH ARE ABLE TO PASS THE WAVE OF DRUGS, AND ITS USE FOR FEEDING OF DRUGS |
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AT (1) | ATE1964T1 (en) |
AU (1) | AU537770B2 (en) |
CA (1) | CA1154294A (en) |
DE (1) | DE3013000C2 (en) |
DK (1) | DK149482C (en) |
ES (1) | ES8206154A1 (en) |
IL (1) | IL62564A (en) |
SU (1) | SU1099831A3 (en) |
ZA (1) | ZA812236B (en) |
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DE3311649C2 (en) * | 1982-04-02 | 1994-08-11 | Nippon Soda Co | Feed additive for ruminants |
DE3230292C2 (en) * | 1982-08-14 | 1986-12-18 | Lohmann Tierernährung GmbH, 2190 Cuxhaven | Particulate feed additive for ruminants and process for their manufacture |
JPS59198946A (en) * | 1983-04-25 | 1984-11-10 | Nippon Soda Co Ltd | Feed additive |
JPS60141242A (en) * | 1983-12-29 | 1985-07-26 | Nippon Soda Co Ltd | Feed additive composition for ruminant |
FR2624351B1 (en) * | 1987-12-15 | 1991-11-22 | Rhone Poulenc Sante | ENZYMATICALLY DEGRADABLE COMPOSITIONS FOR COATING FOOD ADDITIVES FOR RUMINANTS |
FI85093C (en) * | 1988-11-17 | 1992-03-10 | Oeljynpuristamo Oy | Feed and containing metal salt of fatty acid and process for its preparation |
IT1229194B (en) * | 1989-03-03 | 1991-07-25 | Ind Italiana Integratori Trei | CONTROLLED RELEASE PROTECTIVE DIES FOR ZOOTECHNICAL AND VETERINARY USE. |
WO1991012731A1 (en) * | 1990-03-02 | 1991-09-05 | Nippon Soda Co., Ltd. | Feed additive for ruminant |
JPH06339343A (en) * | 1993-04-08 | 1994-12-13 | Ajinomoto Co Inc | Feed additive for ruminant |
CA2140298C (en) * | 1994-01-14 | 1998-12-08 | Thomas L. Meade | Rumen by-pass feed supplement |
JPH09172979A (en) | 1995-12-27 | 1997-07-08 | Ajinomoto Co Inc | Feed additive for ruminant containing new compound salt of phosphoric acid and amino acid and antacid |
WO2006025951A1 (en) * | 2004-08-27 | 2006-03-09 | Archer-Daniels-Midland Company | High-fat animal feed pellets and method for making same |
RU2496327C2 (en) * | 2011-12-07 | 2013-10-27 | Открытое акционерное общество "Ленинградский комбинат хлебопродуктов им. С.М.Кирова" | Fodder additive for heavy milking cows in period of milking |
NL2019737B1 (en) * | 2017-10-16 | 2019-04-23 | Orffa Additives B V | Zinc ricinoleate as mycotoxin inhibitor |
JP7363641B2 (en) * | 2020-03-31 | 2023-10-18 | 日油株式会社 | Feed composition |
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DE287292C (en) * | ||||
US2373763A (en) * | 1941-11-24 | 1945-04-17 | State Of Iowa | Enteric coating |
FR948590A (en) * | 1947-06-27 | 1949-08-04 | Process for coating medicaments in the form of tablets | |
US3037911A (en) * | 1959-09-04 | 1962-06-05 | Merck & Co Inc | Chewable, palatable, vitamin b preparations |
GB1217365A (en) * | 1967-02-23 | 1970-12-31 | Labatt Ltd John | Controlled release feed additives for ruminants |
US3655864A (en) * | 1970-09-21 | 1972-04-11 | Smith Kline French Lab | Glyceryl tristerate and higher fatty acid mixture for improving digestive absorption |
-
1980
- 1980-04-03 DE DE3013000A patent/DE3013000C2/en not_active Expired
-
1981
- 1981-03-13 AT AT81101880T patent/ATE1964T1/en not_active IP Right Cessation
- 1981-03-13 EP EP81101880A patent/EP0037478B1/en not_active Expired
- 1981-03-23 DK DK131381A patent/DK149482C/en active
- 1981-03-23 SU SU813262402A patent/SU1099831A3/en active
- 1981-03-31 AR AR284819A patent/AR231055A1/en active
- 1981-04-02 ES ES500997A patent/ES8206154A1/en not_active Expired
- 1981-04-02 CA CA000374460A patent/CA1154294A/en not_active Expired
- 1981-04-02 ZA ZA00812236A patent/ZA812236B/en unknown
- 1981-04-02 AU AU69045/81A patent/AU537770B2/en not_active Ceased
- 1981-04-02 IL IL62564A patent/IL62564A/en unknown
- 1981-04-02 JP JP56048485A patent/JPS5910780B2/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
IL62564A (en) | 1984-11-30 |
DE3013000A1 (en) | 1981-10-08 |
ES500997A0 (en) | 1982-08-16 |
JPS5910780B2 (en) | 1984-03-12 |
EP0037478B1 (en) | 1982-12-15 |
DK149482C (en) | 1986-12-08 |
DE3013000C2 (en) | 1982-12-09 |
EP0037478A1 (en) | 1981-10-14 |
JPS56154956A (en) | 1981-11-30 |
ES8206154A1 (en) | 1982-08-16 |
AR231055A1 (en) | 1984-09-28 |
DK131381A (en) | 1981-10-04 |
AU6904581A (en) | 1981-10-08 |
CA1154294A (en) | 1983-09-27 |
ATE1964T1 (en) | 1982-12-15 |
SU1099831A3 (en) | 1984-06-23 |
IL62564A0 (en) | 1981-06-29 |
ZA812236B (en) | 1982-04-28 |
AU537770B2 (en) | 1984-07-12 |
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