WO2022112586A1 - Nouvelles formulations sans sucre, leur production et leur utilisation - Google Patents

Nouvelles formulations sans sucre, leur production et leur utilisation Download PDF

Info

Publication number
WO2022112586A1
WO2022112586A1 PCT/EP2021/083504 EP2021083504W WO2022112586A1 WO 2022112586 A1 WO2022112586 A1 WO 2022112586A1 EP 2021083504 W EP2021083504 W EP 2021083504W WO 2022112586 A1 WO2022112586 A1 WO 2022112586A1
Authority
WO
WIPO (PCT)
Prior art keywords
formulation
vitamin
weight
present
ranging
Prior art date
Application number
PCT/EP2021/083504
Other languages
English (en)
Inventor
Jochen Alexander BUTZ
Thomas Joachim HERBRIG
Pelin PALAZOGLU KURK
Frank Theodor MERTIN
Pascal Urs POPP
Christos TSEKOU
Kai Urban
Christian Schaefer
Original Assignee
Dsm Ip Assets B.V.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Dsm Ip Assets B.V. filed Critical Dsm Ip Assets B.V.
Publication of WO2022112586A1 publication Critical patent/WO2022112586A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/15—Vitamins
    • A23L33/155—Vitamins A or D
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K10/00—Animal feeding-stuffs
    • A23K10/20—Animal feeding-stuffs from material of animal origin
    • A23K10/26—Animal feeding-stuffs from material of animal origin from waste material, e.g. feathers, bones or skin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/174—Vitamins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/20—Inorganic substances, e.g. oligoelements
    • A23K20/28—Silicates, e.g. perlites, zeolites or bentonites
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/15—Vitamins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/20—Reducing nutritive value; Dietetic products with reduced nutritive value
    • A23L33/21—Addition of substantially indigestible substances, e.g. dietary fibres
    • A23L33/28—Substances of animal origin, e.g. gelatin or collagen

Definitions

  • the present invention is directed to a formulation with a self-heating temperature 5 ⁇ 120°C, whereby said formulation consists of a fat-soluble vitamin in an amount of at least 25 weight-%, whereby the fat-soluble vitamin is vitamin A or a derivative thereof and optionally vitamin D or a derivative thereof; gelatin in an amount of at least 45 weight-%; at least one antioxidant in an amount of ⁇ 7 weight-%; an anti- caking agent; optionally an oil; optionally residual moisture; whereby the amounts 10 a), b) and c) are based on the total weight of a) to e), as well as to a container with a volume of up to 3000 l comprising such formulation.
  • the present invention is further directed to a process for the manufacture of such formulation, its use as additive to feed and premixes and feed additives, premixes and feed comprising such formulation.
  • the formulation is prepared according to the process as disclosed below, it is also called “beadlets”. It was a surprise that such formulation/beadlets with the advantageous properties as laid down below could be prepared without the use of a sugar as cross-linker. It was further surprising that the self-heating temperature 20 of such formulations/beadlets is increased though their antioxidant content is decreased compared to similar formulations of the prior art. So far it was expected that an amount of at least 10 weight-% of an antioxidant such as e. g. BHT is needed to ensure a self-heating temperature of at least 120°C.
  • Formulations with oxidation sensitive compounds such as fat-soluble vitamins, especially vitamin A, vitamin D and any derivatives and mixtures thereof, have a potential for oxidation processes already at ambient conditions while storing or transporting such formulations.
  • oxidation sensitive compounds such as fat-soluble vitamins, especially vitamin A, vitamin D and any derivatives and mixtures thereof.
  • the storage or transport temperature and the volume of the stored or transported formulation heat accumulation can result which may lead to self-heating and even auto-ignition of such formulations.
  • the oxidation sensitive compounds have to be protected in a suitable matrix and form.
  • Formulations of vitamin A, vitamin D and any derivatives and mixtures thereof having a self-heating temperature ⁇ 100°C, but lower than 120°C have to be stored and transported in flexible intermediate containers with a volume of ⁇ 450 l. Furthermore, they have to be classified as "Dangerous goods class 4.2" and special equipment has to be used for their storage and transport which adds to the overall costs of such formulation.
  • FIBCs flexible intermediate bulk containers
  • the present invention is directed to a formulation with a self-heating temperature ⁇ 120° C consisting of a) a fat-soluble vitamin in an amount of at least 25 weight-%, whereby the fat- soluble vitamin is vitamin A or a derivative thereof and optionally vitamin D or a derivative thereof; b) gelatin in an amount of at least 45 weight-%; c) at least one antioxidant in an amount of ⁇ 7 weight-%; d) an anti-caking agent; e) optionally an oil; f) residual moisture; whereby all amounts a) to e) sum up to 100 weight-% and are based on the total weight of a) to e) together.
  • a self-heating temperature ⁇ 120° C consisting of a) a fat-soluble vitamin in an amount of at least 25 weight-%, whereby the fat- soluble vitamin is vitamin A or a derivative thereof and optionally vitamin D or a derivative thereof; b) gelatin in an amount of at least 45 weight-%; c) at least one antioxidant in
  • composition does not comprise any further ingredients besides a) to f). It also means that the formulation does e. g. not comprise a lignosulfonate.
  • the amount of residual moisture is preferably at most 6 weight-%, more preferably at most 5 weight-%, even more preferably at most 3.5 weight-%, most preferably at most 2 weight-%, based on the total weight of the formulation, i.e. the total weight of a) to f).
  • the minimum amount of moisture is preferably 0.1 weight-%, based on the total weight of the formulation.
  • step E) of the process according to the present invention the moisture content is lower than without step E) being performed.
  • the amount of antioxidant is low in these formulations, they show a self- heating temperature ⁇ 120°C. Furthermore, they show a good stability and a good homogeneity in premixes.
  • the formulations of the present invention show also a high stability under pelleting conditions.
  • the formulations according to the present invention show a self-heating temperature ⁇ 120°C and a DT ⁇ 60 K, they can be transported in containers, especially in FIBCs ("flexible intermediate bulk container"), of volumes up to 3000 l, preferably in containers, especially in FIBCs, of volumes ranging from 450 Ito 3000 1.
  • FIBCs flexible intermediate bulk container
  • the samples are placed in a cubic shaped wire basket (either 16 ml or 1000 ml) in the center of an oven.
  • the temperature of the oven is measured at two spots and remains constant during the testing period (24 hours), i.e. so called "isoperibolic test".
  • the temperature probe for the sample is placed in the center of the sample. Then the sample temperature reaches a temperature being 2 K below the oven temperature the 24 hour testing period starts.
  • the formulations of the present invention show a self-heating temperature ⁇ 120°C and a DT ⁇ 60 K, especially on large scale production of several thousand tons.
  • any kind of container with a volume up to 3000 l preferably with a volume ranging from 450 to 3000 l, more preferably with a volume ranging from 480 to 2000 l, even more preferably with a volume ranging from 500 to 1500 l and from 500 to 1000 l, most preferably with a volume ranging from 600 to 800 l, may be used.
  • a “flexible intermediate bulk container” (“FIBC”), "jumbo”, “bulk bag”, “super sack”, “tote bag”, or “big bag”, is an industrial container made of flexible fabric that is designed for storing and transporting dry, flowable products, such as sand, fertilizer, and feed additives.
  • FIBCs are most often made of thick woven polyethylene or polypropylene, either coated or uncoated, and normally measure around 45-48 inches (114-122 cm) in diameter and varies in height from 100 to 200 cm (39 to 79 inches). Its capacity is normally around 1,000 kg or 2,200 lb, but the larger units can store even more.
  • a bulk bag designed to transport one metric ton (0.98 long tons; 1.1 short tons) of material will itself only weigh 5-7 lb (2.3-5.0 kg).
  • Bags are made with either one, two or four lifting loops.
  • the single loop bag is suitable for one man operation as there is no need for a second man to put the loops on the loader hook.
  • Emptying is made easy by a special opening in the bottom such as a discharge spout, of which there are several options, or by simply cutting it open.
  • a big bag with four lifting loops is used. Its volume preferably ranges from 480 to 2000 l, more preferably from 500 to 1500 l, even more preferably from 500 to 1000 l, most preferably from 600 to 800 l.
  • a loading with 200 to 1500 kg of the formulation according to the present invention is preferred. More preferred is a loading with 300 to 1200 kg of the formulation according to the present invention. Most preferred is a loading with 500 to 900 kg of the formulation according to the present invention.
  • the present invention is also directed to a big bag, especially to a big bag with 3 or more lifting loops such as e. g. 4 lifting loops, having a volume ranging from 480 l to 2000 l and comprising a formulation according to the present invention with the preferences as given below.
  • the FIBC has an "inliner", which protects its content from light, oxygen and water, as well as if it is a Type C FIBC. Openings at the top for loading and at the bottom for unloading are convenient. Therefore, such openings are preferably present. Such openings will be tightly closed during storage and transport.
  • the formulation is described in more detail below.
  • the essential ingredients and their amounts, as well as the ingredients being absent in the formulations are further disclosed.
  • the formulation of the present invention does not comprise any further ingredients besides a) to f).
  • the non ⁇ present ingredients are further exemplified and listed below.
  • the matrix of the formulations of the present invention does not comprise any of the following salts: water-soluble salts of carboxylic acids, sodium carbonate, potassium carbonate, calcium sulfate, and calcium phosphate.
  • water-soluble salts of carboxylic acids not being present in the matrix of the formulations of the present invention are: aluminum subacetate, sodium tartrate, sodium glutarate, sodium acetate, calcium acetate, sodium propionate, calcium propionate and sodium benzoate.
  • Some of these salts may, however, be used as anti-caking agents during drying of the formulation, especially during the powder-catch process step.
  • the formulations of the present invention do not comprise any of these salts; i.e. no water-soluble salts of carboxylic acids, no sodium carbonate, no potassium carbonate, no calcium sulfate, and no calcium phosphate.
  • the process of the present invention has the advantage that no organic solvent except water is used, so that the formulation according to the present invention is substantially free of organic solvents, "substantially free” means that the amount thereof is ⁇ 5 weight-%, preferably ⁇ 3 weight-%, more preferably ⁇ 1 weight-%, even more preferably ⁇ 0.5 weight-%, most preferably ⁇ 0.1 weight-%.
  • formulations according to the present invention do neither comprise any reducing sugars nor any non-reducing sugars.
  • reducing sugars examples include aldohexoses and ketohexoses with a hydroxy group in a-position such as e.g. glucose, fructose, galactose and any mixture thereof.
  • Reducing disaccharides such as e.g. lactose and maltose and reducing oligosaccharides, as well as aldopentoses and ketopentoses with a hydroxy group in a-position are also not part of the formulation according to the present invention.
  • the formulations of the present invention neither invert sugar nor glucose syrup nor high fructose corn syrup are present.
  • the formulations according to the present invention do not comprise any oligo- and polysaccharides in their matrix.
  • Polysaccharides such as starch may, however, be used as anti-caking agent during the drying of the formulation according to the present invention.
  • polyhydric alcohols examples include glycerol, monoesters of glycerol with C 1-5 monocarboxylic acids, monoethers of glycerol, diglycerol, triglycerol, polyglycerol, propylene glycol, dipropylene glycol, 1,3-butylene glycol, ethylene glycol, polyethylene glycol, sorbitol, xylitol, maltitol, erythritol, mannitol, etc.
  • cross-linking agent such as e.g. acetaldehyde, glutaraldehyde or glyoxal are present in the formulations of the present invention.
  • Ethoxyquin also known as "EMQ" (lUPAC name: 6-Ethoxy-2,2,4-trimethyl-1,2- dihydroquinoline), is also not present in the formulations of the present invention; whereas according to EP-A 494417 the presence of ethoxyquin is necessary to obtain stable formulations.
  • lignosulfonates that are not present in the formulations of the present invention are: sodium lignosulfonate, ammonium lignosulfonate, magnesium lignosulfonate, calcium lignosulfonate; as well as any of their mixtures.
  • lignosulfonates Suppliers of lignosulfonates are: Borregaard Industries Limited, Norway; Burgo Group, Rayonier Advanced Materials, Wuhan Xinyingda Chemicals, Shenyang Xingzhenghe Chemical, Abelin Polymers, GREENAGROCHEM, Harbin Fecino Chemical, Karjala Pulp, Nippon Paper Industries, Pacific Dust Control, Sappi, The Dallas Group of America, Venki Chem and Xinyi Feihuang Chemical.
  • fat-soluble vitamins comprises for the purpose of the present invention vitamins A and/or D, the corresponding derivatives such as esters, especially C 1 C 20 alkyl esters, with an action resembling that of vitamin A or D, as well as any mixture thereof.
  • Vitamin D means either Vitamin D 3 (cholecalciferol) or Vitamin D 2 (ergocalciferol) or both.
  • Vitamin D derivative means any derivative of Vitamin D as for example 25- hydroxy vitamin D 3 (so-called “HyD”), 1,25-dihydroxy vitamin D 3 or 24,25-di hydroxy vitamin D 3 .
  • fat-soluble vitamins are vitamin A, vitamin A acetate, vitamin A propionate, vitamin A butanoate, vitamin A palmitate, vitamin D 3 and 25-hydroxy-vitamin D, as well as any mixture thereof. More preferred are vitamin A acetate, vitamin D 3 and any mixture thereof. Most preferred the fat- soluble vitamin is vitamin A acetate or a mixture of vitamin A acetate and vitamin D3, preferably in a weight ratio of vitamin A acetate to vitamin D3 ranging from 1:1 to 100:1, more preferably ranging from 10:1 to 85:1.
  • the amount of the vitamin A or its derivative thereof is chosen in such a way so that its final amount in the formulation is preferably in the range of from 25 to 60 weight-%, more preferably its final amount is in the range of from 28 to 55 weight- %, even more preferably its final amount is in the range of from 30 to 50 weight-% and from 32 to 48 weight-%, most preferably its final amount is in the range of from 35 to 46 weight-%, based on the total weight of a) to e).
  • any combination of any lower value with any other value to a range is also disclosed, i.e. 28-60 weight-%, 30-48 weight-%, 25-46 weight-% etc.
  • the amount of vitamin A acetate is as given above for the vitamin A derivative and the amount of vitamin D3 is chosen in such a way so that its final amount in the formulation is preferably in the range of from 0.01 to 10 weight-%, more preferably its final amount is in the range of from 0.05 to 5 weight-%, even more preferably its final amount is in the range of from 0.1 to 3.5 weight-%, most preferably its final amount is in the range of from 0.3 to 2.5 weight-%, based on the total weight of a) to e).
  • any combination of any lower value with any higher value to a range is also disclosed, i.e. 0.01-5 weight-%, 0.05-10 weight-%, 0.1-5 weight-% etc.
  • vitamin D preferably vitamin D 3
  • an oil is present.
  • oils can be from any origin. They can be natural, modified or synthetic. If the oils are natural they can be plant or animal oils.
  • the term "oil” encompasses any vegetable oil or fat like corn oil, sunflower oil, soybean oil, safflower oil, rapeseed oil, peanut oil, palm oil, palm kernel oil, cotton seed oil, olive oil, coconut oil, canola oil, sesame oil, hazelnut oil, almond oil, cashew oil, macadamia oil, mongongo nut oil, pracaxi oil, pecan oil, pine nut oil, pistachio oil, sacha Inchi (Plukenetia volubilis) oil, walnut oil, as well as middle chain triglycerides ("MCT”) and any mixture thereof.
  • corn oil, peanut oil, safflower oil or sunflower oil are used.
  • the weight ratio of vitamin D to the oil is preferably ranging from 1:1 to 1:10, more preferably from 1:2 to 1:5.
  • Suitable gelatins are poultry gelatin, porcine gelatin, bovine gelatin and any mixture thereof, as well as fish gelatin and any mixture with the other gelatins.
  • the gelatin is generally classified according to its Bloom value.
  • Type A gelatin is obtained from acid processing of collagen.
  • Type B gelatin is obtained from alkaline processing of collagen.
  • Bloom is a test to measure the strength of a gel of gelatin. The test determines the weight (in grams) needed by a probe (normally with a diameter of 0.5 inch) to deflect the surface of the gel 4 mm without breaking it. The result is expressed in bloom (grades).
  • gelatins with a Bloom ranging from 0 to 300 may be used.
  • Low bloom, medium bloom and high bloom gelatin are gelatins having a strength of less than about 120 Bloom (low Bloom), between about 120 and up to 200 Bloom (medium Bloom) or a strength of more than about 200 Bloom (high Bloom).
  • Low bloom gelatin preferably gelatin with Bloom ranging from 0 to ⁇ 120, more preferably gelatin with 60-110 Bloom, even more preferably gelatin with 70-90 Bloom, most preferably gelatin with 80 Bloom
  • medium bloom gelatin preferably-gelatin with 120-160 Bloom, more preferably gelatin with 140 Bloom
  • high Bloom gelatin preferably gelatin with 200-300 Bloom, more preferably gelatin with 200-270 Bloom, even more preferably gelatin with 200-250 Bloom, most preferably gelatin with 200 Bloom.
  • the amount of gelatin in the formulations of the present invention is chosen in such a way so that its final amount in the formulation is preferably at least 46 weight-%, more preferably at least 48 weight-%, even more preferably at least 50 weight-%, most preferably at least 51 weight-%, based on the total weight of a) to e).
  • the maximum amount of gelatin in the formulation may preferably be 70 weight-%, more preferably 65 weight-%, even more preferably 62 weight-%, 60 weight-% and 58 weight-%, and most preferably 55 weight-%, based on the total weight of a) to e).
  • any combination of any lower value with any higher value to a range is also disclosed, i.e. 46-65 weight-%, 51-55 weight- %, 50-70 weight-% etc.
  • the antioxidant may be a water-soluble antioxidant or a fat-soluble antioxidant or any mixture thereof.
  • mixtures of water-soluble antioxidants, mixtures of fat- soluble antioxidants and mixtures of one or more water-soluble antioxidants and one or more fat-soluble antioxidants are also included in the term "antioxidant".
  • Preferred are fat-soluble antioxidants as well as mixtures thereof and mixtures of water- and fat-soluble antioxidants.
  • Inorganic antioxidants may also be present.
  • inorganic antioxidants NaBH 4 , Na 2 S0 3 and/or Na 2 S 2 0 3 .
  • BHA butylated hydroxyanisoles
  • BHT butylated hydroxytoluenes
  • eugenol 2- Methoxy-4
  • Analogues of tocopherols and tocotrienols are especially compounds with a shorter side chain in position 2 compared to tocopherols and tocotrienols.
  • the BHA is preferably a mixture of 2-tert-butyl-4-hydroxy-anisole and 3-tert-butyl- 4-hydroxy-anisole.
  • LUPAC name 2,6-di-tert-butyl-4-methylphenol.
  • water-soluble antioxidants are ascorbic acid and its salts such as e.g. sodium ascorbate, citric acid and its salts such as e.g. sodium citrate, as well as any mixture thereof.
  • Preferred examples of mixtures of water- and fat-soluble antioxidants are tocopherol and sodium ascorbate, tocopherol and ascorbic acid, whereby the tocopherol may be alpha-, beta-, gamma- or delta-tocopherol, preferably whereby the tocopherol is alpha- or delta-tocopherol, more preferably whereby the tocopherol is alpha-tocopherol, most preferably whereby the tocopherol is DL- alpha-tocopherol.
  • tocopherols are compounds of formula (ll), wherein one of the two substituents R 1a and R 2a is C 12 -alkyl and the other of the two substituents R 1a and R 2a is either hydrogen or C 1-5 -alkyl or (CH 2 ) n -OH with n being an integer from 1 to 5, and wherein A is CH(R 3a ), and wherein R 3a , R 4a and R 6a are independently from each other H or C 1-4 -alkyl, and wherein R 5a is H or OH or C 1-4 -alkyl or C 1-4 -alkoxy, as disclosed in WO 2019/185938.
  • Preferred examples of the antioxidants of formula (ll) as disclosed in WO 2019/185894 are the following compounds of formula (1)-(11) with "Me” being methyl:
  • R 1b and R 2b are independently from each other H or C 1-11 -alkyl or (CH 2 ) n — OH with n being an integer from 1 to 6 or R 1b and R 2b together represent a keto group, and wherein R 3b , R 4b , R 5b , and R 6b are independently from each other H or C 1-6 -alkyl or C 1-6 -alkoxy, and R 7b is H or C 1-6 -alkyl, as disclosed in WO 2019/185898.
  • alkyl and alkoxy hereby encompass linear alkyl and branched alkyl, and linear alkoxy and branched alkoxy, respectively.
  • Preferred examples of compounds of formula (III) and (IV) are the following compounds (12)-(19):
  • antioxidants are compounds of formula (V), whereby R 1 , R 2 and R 3 are independently from each other H or linear C 1-6 -alkyl or branched C 3-8 -alkyl, whereby preferably R 1 is H or methyl or ethyl or n-propyl or /so-propyl or tert- butyl and R 2 and R 3 are independently from each other H or methyl or ethyl, with the further preferences as disclosed in WO 2019/185940.
  • the compounds of formula (VI) with n being 1 or 2, R 1b and R 3b being independently from each other H or C 1-5 -alkyl, and R 2b being either H or C 1-5 -alkyl or Ci-5-alkyloxy, preferably with the proviso at least one of R 1b , R 2b and R 3b being H, as disclosed in WO 2019/185904 can be used as antioxidants in the formulations of the present invention.
  • the following compounds of formulae (VI-1) and (VI-2) are especially preferred:
  • suitable antioxidants are compounds of the following formulae (VII) and (VI II) with R 1c , R 2c and R 3c being independently from each other H or C 1-4 -alkyl as published in WO 2019/185942 and WO 2019/185888, respectively.
  • Preferred examples thereof are tocotrienols and tocopherols of the formulae (20) to (27) as shown below.
  • the asterisks * mark each a chiral/stereogenic center.
  • the term "compound of formula (VI l)/(VI II)” encompasses all possible isomers having any configuration at said centers.
  • Suitable polyphenols are 2,4,5-trihydroxybutyrophenone, epigallo- catechin gallate ("EGCG”), epigallo-catechin, gallo-catechin, hydroxytyrosol, resveratrol, carnosol, 2-(3,4-dihydroxyphenyl)acetic acid and Ci- 6 alkyl esters thereof, and any mixture thereof.
  • examples of preferred esters are Ci- 20 alkyl esters of gallic acid such as e.g. propyl gallate, octyl gallate or dodecyl gallate, and Ci- 20 alkyl esters of syringic acid.
  • ferulic acid 3-(4-hydroxy-3- methoxy
  • Examples of derivatives of cinnamic acid are Z-ethoxyethyl p-methoxycinnamate, ethylhexyl p-methoxycinnamate, 2-ethylhexyl 4-methoxycinnamate, methyl diiso- propylcinnamate, isoamyl 4— methoxycinnamate, and diethanolamin 4-methoxy ⁇ cinnamate.
  • BHT butylated hydroxytoluene
  • lUPAC name 2,6-di-tert-butyl-4-methylphenol
  • the weight ratio of DL-alpha-tocopherol to sodium ascorbate and of DL-alpha- tocopherol to ascorbic acid is preferably ranging from 5:1 to 1:5, more preferably from 3:1 to 1:3, even more preferably from 2:1 to 1:2, most preferably from 1.1:1 to 1:1.1.
  • the total amount of the antioxidant(s) in the formulations of the present invention is lower than in gelatin-based formulations already being on the market.
  • the total amount of the antioxidant(s) is chosen in such a way so that its/their final amount in the formulation is preferably ⁇ 6.7 weight-%, more preferably its/their final amount is in the range of from 0.1 to 6.0 weight-% and from 0.2 to 5.5 weight-%, even more preferably its/their final amount is in the range of from 0.3 to 5.0 weight-% and from 0.4 to 4.8 weight-%, most preferably its/their final amount is in the range of from 0.5 to 4.6 weight-% and from 0.5 to 2.5 weight-%, based on the total weight of a) to e) in the formulation.
  • any combination of any lower value with any higher value to a range is also disclosed, i.e. at least 0.5 and at most 6.7 weight-%, 0.3 to 2.5 weight-%; etc.
  • Table I All amounts are based on the total weight of a), b), c), d) and e) in the formulation.
  • any value may be combined with any value of another column.
  • Suitable organic anti-caking agents are corn starch, as well as starches from other botanical sources such as e.g. as waxy corn, wheat, tapioca, pea and potato, as well as derivatives thereof such as pre-gelatinised starch, starch ethers (e.g. carboxymethyl starch), starch esters (e.g. starch monophosphate, alkenyl- succinated starch, especially octenyl-succinated starch), cross-linked starch and oxidized starch and any mixture thereof.
  • Other suitable organic anti-caking agents are talc, cellulose, microcrystalline cellulose, cellulose derivatives or fibres, ferric ammonium citrate, sodium salts of fatty acids such as e.g.
  • potassium salts of fatty acids such as e.g. potassium stearate
  • calcium salts of fatty acids such as e.g. calcium stearate
  • magnesium salts of fatty acids such as e.g. magnesium stearate
  • aluminum salts of fatty acids such as e.g. aluminum stearate
  • ammonium salts of fatty acids such as e.g. ammonium stearate, and any mixture of any of them.
  • suitable anti-caking agents are inorganic anti-caking agents such as e.g.
  • silicic acid H2 n+ 2Si n 03 n+i and alkaline/earth alkali metal salts thereof, precipitated silicic acid, silica ( silicon dioxide), modified silica, hydrophobically modified silica, precipitated silica, magnesium oxide, dicalcium diphosphate, tricalcium phosphate, magnesium phosphate, sodium carbonate, potassium carbonate, calcium carbonate, magnesium carbonate, calcium oxide, magnesium oxide, potassium silicate, calcium silicate, magnesium silicate, magnesium trisilicate, aluminum silicate, sodium aluminum silicate, potassium aluminum silicate, calcium aluminum silicate, zeolithe (aluminosilicates), disodium sulfate or mixtures thereof.
  • Further suitable inorganic anti-caking agents are bentonite and kaolin.
  • mixtures of organic and inorganic anti-caking agents may be used.
  • the preferred anti-caking agents used in the formulations of the present invention are anti-caking agents with a particle size D(v,50%) from 100 nm to 10 pm, preferably from 100 nm to 9 pm, more preferably from 150 nm to 5 pm, measured as dry dispersion with a Malvern MasterSizer 3000 (laser diffraction).
  • the particle size of the anti-caking agent can be determined with a laser diffraction system e.g. Malvern MasterSizer 3000, either as dry dispersion or as wet dispersion in oil or Volasil (a mixture of volatile and cyclic silicones such as octamethylcyclo- tetrasiloxane and decamethylcyclopentasiloxane).
  • the particle size can also be determined with electron microscopy.
  • the more preferred anti-caking agents are silicic acid Hh n+ zSi n Ch n+i , silica, microcrystalline cellulose, as well as any mixture thereof.
  • the most preferred anti-caking agents are hydrophilic precipitated silicic acid H2n+2Sin03n+i, hydrophilic precipitated silica and any mixture thereof.
  • the amount of the anti-caking agent is chosen in such a way so that its final amount in the formulation is preferably ranging from 1-10 weight-%, more preferably ranging from 3 to 9 weight-%, most preferably ranging from 4.5 to 7.5 weight-%, based on the total weight of the formulation.
  • its final amount in the formulation is preferably ranging from 1-10 weight-%, more preferably ranging from 3 to 9 weight-%, most preferably ranging from 4.5 to 7.5 weight-%, based on the total weight of the formulation.
  • the formulations of the present invention show preferably a bulk density ranging from 0.58-0.7 g/cm 3 , more preferably a bulk density ranging from 0.60-0.67 g/cm 3 , most preferably a bulk density ranging from 0.61-0.65 g/cm 3 .
  • the formulations of the present invention show preferably a tap density ranging from 0.6-0.7 g/cm 3 , more preferably a tap density ranging from 0.62-0.69 g/cm 3 , most preferably a tap density ranging from 0.64-0.68 g/cm 3 .
  • the bulk density and the tap density are measured as follows:
  • a 250 ml glass cylinder is filled with the sample. The volume and the weight are measured. Bulk density is the weight divided by the volume.
  • the sample is tapped with a 2000 Taps with a Stampfvolu meter JEL STAV II (J. Engelsmann AG). The tapped volume is measured. Tap density is the weight divided by the tapped volume.
  • the formulations of the present invention show besides the bulk density and/or tap density above, also the particle sizes and/or particle size distribution as cited below, which results in a very good homogeneity when mixed into feed.
  • Table II and Table III show preferred formulations of the present invention and their composition.
  • Vitamin A acetate another Vitamin A C 1-20 alkyl ester, preferably another Vitamin A C 2-16 alkyl ester, may also be used.
  • the formulations according to Table II consist only of vitamin A acetate and optionally vitamin D3, gelatin, a phenol with bulky alkyl groups as antioxidant, optionally an oil, an anti-caking agent and optionally residual moisture.
  • the formulations according to Table III consist only of vitamin A acetate and optionally vitamin D3, gelatin, a mixture of antioxidants, optionally an oil, an anti ⁇ caking agent and optionally residual moisture.
  • the amounts of the oil, if present, are as disclosed above.
  • Especially preferred formulations of the present invention are the following formulations A to D, whereby the amounts of the single ingredients are given in weight-% and are based on the total weight of all ingredients cited in the corresponding tables below excludingthe residual moisture.
  • the amounts of all ingredients cited in the corresponding tables below always sum up to 100 weight- %.
  • the amount of moisture is preferably in the range of 1-4 weight-% and based on the total weight of the corresponding formulation.
  • the formulations only contain the ingredients cited in the corresponding tables and no further ingredients. Thus, the formulations consist only of the ingredients as cited in the corresponding tables.
  • Vitamin D3 is additionally present in the Formulation A, its amount is in the range of 2-3 weight-%, based on the total weight of the ingredients cited in the corresponding table above. Furthermore, preferably also an oil is then present with the preferences as given above. In this case the amount of gelatin is reduced accordingly.
  • Formulation B is then present with the preferences as given above. In this case the amount of gelatin is reduced accordingly.
  • Vitamin D3 is additionally present in the Formulation B, its amount is in the range of 2-3 weight-%, based on the total weight of the ingredients cited in the corresponding table above. Furthermore, preferably also an oil is then present with the preferences as given above. In this case the amount of gelatin is reduced accordingly.
  • Vitamin D3 is present in the Formulation C, preferably also an oil is present with the preferences as given above. In case neither Vitamin D3 nor an oil is present, the amount of gelatin is increased accordingly.
  • Vitamin D3 is present in the Formulation D, preferably also an oil is present with the preferences as given above. In case neither Vitamin D3 nor an oil is present, the amount of gelatin is increased accordingly.
  • a sieve test can be performed with filters of 850 pm pores (mesh 20), 425 pm pores (mesh 40) and 150 pm pores (mesh 100).
  • the particle size of the solid formulation may also be determined by laser diffraction analytic whereby the dry dispersion of the sample is measured with a Malvern Mastersizer 2000 or 3000 and Fraunhofer calculation.
  • the particle sizes of the formulation, when determined with laser diffraction with a Malvern Mastersizer 3000 and Fraunhofer calculation, are as follows:
  • D(v,10%) 150-270 pm, preferably 160-250 pm;
  • the formulation of the present invention is preferably manufactured according to a process comprising the following steps:
  • step C) Emulsifying the active phase obtained in step B) into the matrix obtained in step A) to obtain a dispersion
  • step D) Spray-drying the dispersion obtained in step C) in presence of an anti- caking agent to obtain the formulation.
  • the amounts of the gelatin b), and if present, the water-soluble antioxidant c) are chosen so that the final amounts of these compounds in the solid formulation after having performed steps A) to D) and A) to E), respectively, is as described above.
  • Step A) is preferably performed at a temperature ranging from 40 to 80°C, more preferably ranging from 50 to 75°C, most preferably ranging from 55 to 70°C.
  • Step B) is preferably performed at a temperature to bring the components a) and c) into a liquid state.
  • vitamin D preferably vitamin D3
  • the vitamin D is preferably added to the other fat-soluble vitamin and the fat-soluble antioxidant as oily suspension, whereby the weight ratio of vitamin D to the oil is preferably ranging from 1:1 to 1:10, more preferably from 1:2 to 1:5.
  • the vitamin D is preferably added to the fat-soluble antioxidant as oily suspension, whereby the weight ratio of vitamin D to the oil is preferably ranging from 1:1 to 1:10, more preferably from 1:2 to 1:5 Step C)
  • this step is performed at a mixing temperature in the range of from 40 to 75°C, more preferably at a mixing temperature in the range of 50 to 70°C, even more preferably at a mixing temperature in the range of 55°C to 65°C to obtain a dispersion.
  • the homogenization can be achieved by using a rotor-stator device or a high- pressure homogenizer or both. Other devices known to the person skilled in the art may also be used.
  • Step D) The dividing and drying of the mixture of the oil-in-water preparation to produce the solid formulation according to the present invention can be done in any conventional way, such as spray cooling, modified spray cooling, spray drying, spray-drying in combination with fluidized bed granulation, modified spray drying or sheet drying and crushing, see e.g. WO 91/06292 A1.
  • the conversion to the solid formulation is achieved by a powder-catch technique, whereby the sprayed dispersion droplets are caught by the anti-caking agent (so-called "catch media”), and dried.
  • thermo treating it is advantageous to treat the powder obtained after having performed step D) thermally.
  • temperatures of up to 125°C are applied, more preferably the thermal treating is carried out at a temperature ranging from 80- 120° C, even more preferably the thermal treating is carried out at a temperature ranging from 100 to 120°C, most preferably the thermal treating is carried out at a temperature ranging from 110 to 120°C.
  • the amount of moisture in the formulation is decreased.
  • the process for the manufacture of the formulation according to the present invention does neither comprise a crosslinking step performed by exposure to radiation nor does it comprise a crosslinking step performed by using an enzyme.
  • the present invention is also directed to the use of the formulation according to the present invention with the preferences as given above as additive to feed or premixes.
  • Feed additive, premix and feed according to the present invention are Feed additive, premix and feed according to the present invention.
  • the present invention is also directed to a feed additive, a premix and a feed comprising the formulation according to the present invention with the preferences as given above.
  • Feed means any substance or product, including additives, whether processed, partially processed or unprocessed, intended to be used for oral feeding to animals.
  • Feed in the context of the present invention is especially feed for broilers including starter, grower, finisher; broiler breeders including starter, grower (pullets), layers and male breeders, for layers and other poultry such as e.g.
  • turkeys including starter, grower, finisher; for turkey breeders including starter, grower, layers and male breeders, for ruminants including calves, milk replacer, heifers, beef cattle, breeding bulls, sheep and goats; for horses, especially foals, leisure horses, race horses, mares and stallions, for rabbits, for mick and foxes, for swine including fattening pigs: pre-starter, starter, grower, finisher; breeders: replacement gilts, sows, boars, and feed for companion animals, especially for dogs and cats.
  • the amount of the formulation and the fat-soluble vitamin respectively follows the regulatory guidelines in the regions depending on the specific animal species and its age.
  • I.U. is used as a universal unit for fat soluble vitamins because there are different forms of the vitamins with varying amounts of fat-soluble vitamins.
  • the formulation according to the present invention is usually added to feed in form of a premix, i.e. a mixture with other micro-nutrients such as other vitamins or their formulations and minerals.
  • a premix i.e. a mixture with other micro-nutrients such as other vitamins or their formulations and minerals.
  • the premix inclusion in feed is ⁇ 1 weight-% for many species.
  • the amount of the formulation according to the present invention needed to be included into the feed is calculated based on the active content of the feed and the targeted dosage of the fat-soluble vitamin in the final feed considering said inclusion level.
  • the conversion factors of the fat-soluble vitamins are as follows: 1 I.U. Vitamin A corresponds to 0.344 ⁇ g of Vitamin A acetate;
  • Vitamin D 3 corresponds to 0.025 ⁇ g of Vitamin D 3 .
  • Table IV shows the amounts of the fat-soluble vitamins added per kg of air-dry feed. The exact amount is depending on several factors such as phase/age of the animal, animal species and legal local limits.
  • the feed for poultry differs from region to region.
  • Tables V and VI typical examples for diets in Europe and Latin America are given. These diets include cereals such as wheat, rye, maize/corn, minerals such as NaCl, vegetable oils such as soya oil, amino acids and proteins.
  • the present invention is also directed to feed for poultry comprising the formulation according to the present invention; preferably to feed for poultry comprisingthe formulation accordingtothe present invention and cereals, minerals, vegetable oils, amino acids and proteins.
  • Pet food Pet foods are formulated to meet nutrient specifications using combinations of multiple ingredients to meet the targeted nutrient specification.
  • the present invention is also directed to pet food comprising the formulation according to the present invention; preferably to pet food comprising the formulation according to the present invention and animal meals and/or fresh meats, vegetable proteins, grains, fiber sources, fats and/or oils, micronutrients, palatants and optionally other non-basic ingredients.
  • the present invention is also directed to feed for swine comprising the formulation according to the present invention; preferably to feed for swine comprising the formulation according to the present invention and corn, soybean meal, minerals, vegetable oils, amino acids, further vitamins and trace mineral premixes.
  • Example 8 shows the stability of a formulation according to the present invention in a premix.
  • Example 9 shows the stability of a formulation according to the present invention in feed pelleting.
  • the matrix components i.e. gelatin and optionally the water-soluble antioxidant are dissolved in water at approximately 65°C to obtain the "matrix".
  • Vitamin A acetate, Vitamin D3 (if present) and the fat-soluble antioxidant are heated at approximately 65°C under stirring until complete melting of vitamin A acetate ("active phase"). They are then emulsified into the matrix.
  • the resulting dispersion is sprayed into a spray tower in the presence of an anti-caking agent to form droplets of the desired size.
  • the solidified droplets are then dried by an drying air of various temperatures (5-75°C).
  • the dried powder is separated from the majority of the anti-caking agent and sieved through 150 pm and 600 pm filters.
  • the powder is further treated at a temperature of up to 120°C in a mixer or in a fluid bed, whereby it is made partially water-insoluble.
  • the particle size of the dried and thermically-treated powder is determined with laser diffraction analytic with a Malvern Mastersizer 3000.
  • the sample is hereby dry dispersed.
  • the Fraunhofer theory the particle size distribution of the sample is calculated.
  • the bulk and the tap density are measured according to the procedures described above.
  • the self-heating temperature is determined according to the following procedure. Determination of the self-heating temperature
  • the samples are placed in a cubic shaped wire basket (either 16 ml or 1000 ml) in the center of an oven.
  • the temperature of the oven is measured at two spots and remains constant during the testing period (24 hours), i.e. so called "isoperi bolic test".
  • the temperature probe for the sample is placed in the center of the sample. Then the sample temperature reaches a temperature being 2 K below the oven temperature the 24 hour testing period starts.
  • n.d. not determined. All amounts are given in weight-%. The amounts a), b), c) and d) together sum up to 100 weight-%. he residual moisture content is based on the total weight of the formulation.
  • Example 7 is prepared at large scale in an analogous way according to General Procedure I described above. Also, at large scale a formulation with a self-heating temperature ⁇ 120°C and a DT ⁇ 60 K is obtained.
  • Table 2 All amounts are based on the total weight of Vitamin A acetate, Vitamin D3, gelatin, 2,6-di-tert-butyl-p-cresol and silica together.
  • Example 8 Testing of the stability of the formulation according to example 4 in a premix
  • the premix "P25br” in which the stability of the formulation according to example 4 is examined has the composition as shown in Table 3.
  • the amount of the formulation added per kg of premix is calculated so that a targeted Vitamin A content in the premix of 2'500'000 I.U./kg is reached.
  • This premix contains choline chloride in a high amount, as well as Cu and Zn. Choline chloride and high concentrations of Cu and Zn are known to reduce the stability of vitamin A (see e.g. Pan Yang et al., Animals 2019, 9, 1154 ff.). Thus, the chosen premix "P25br" is quite aggressive. If such premix shows a retention of vitamin A ⁇ 70% after storage for one month at 30°C and 65% of relative humidity that means that the vitamin A formulation used has a good stability in premixes.
  • the average retentions and coefficient variations are calculated. They are as follows:
  • the formulation according to the present invention has a good stability in premixes.
  • Example 9 Testing of the stability of the formulation according to example 7 in feed
  • the feed "WMaisFH" a wheat-corn-based broiler diet, in which the stability of the formulation according to example 7 is examined has the composition as shown in Table 4.
  • the amount of the formulation added per kg of premix is calculated so that a targeted Vitamin A content in the premix of 50 ⁇ 00 I.U./kg is reached.
  • test batches are pelleted in a Biihler DFPL pellet mill, using the parameters given in here:
  • Example 7 demonstrates that the formulations of the present invention are highly stable under pelleting conditions.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Mycology (AREA)
  • Animal Husbandry (AREA)
  • Nutrition Science (AREA)
  • Inorganic Chemistry (AREA)
  • Biomedical Technology (AREA)
  • Biotechnology (AREA)
  • Molecular Biology (AREA)
  • Physiology (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne une formulation ayant une température d'auto-échauffement ≥ 120 °C. Ladite formulation est composée d'une vitamine liposoluble à raison d'au moins 25 % en poids, la vitamine liposoluble étant la vitamine A ou un dérivé de celle-ci et éventuellement la vitamine D ou un dérivé de celle-ci ; de gélatine à raison d'au moins 45 % en poids ; d'au moins un antioxydant en une quantité ≤ 7 % en poids ; d'un agent anti-agglomérant ; éventuellement d'une huile ; éventuellement d'humidité résiduelle ; les quantités de a), b) et c) étant basées sur le poids total de a) à e). La présente invention concerne en outre un contenant ayant un volume allant de 450 l à 3 000 l comprenant une telle formulation, un procédé de production d'une telle formulation, l'utilisation d'une telle formulation en tant qu'additif pour des aliments pour animaux ou des prémélanges, et des additifs d'aliments pour animaux, des prémélanges ou des aliments pour animaux comprenant une telle formulation.
PCT/EP2021/083504 2020-11-30 2021-11-30 Nouvelles formulations sans sucre, leur production et leur utilisation WO2022112586A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP20210832.0 2020-11-30
EP20210832 2020-11-30

Publications (1)

Publication Number Publication Date
WO2022112586A1 true WO2022112586A1 (fr) 2022-06-02

Family

ID=73654627

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2021/083504 WO2022112586A1 (fr) 2020-11-30 2021-11-30 Nouvelles formulations sans sucre, leur production et leur utilisation

Country Status (1)

Country Link
WO (1) WO2022112586A1 (fr)

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991006292A1 (fr) 1989-11-02 1991-05-16 Danochemo A/S Procede de preparation d'un solide hydrophobe ou aerophile dispersible dans l'eau
EP0494417A2 (fr) 1991-01-10 1992-07-15 Basf Corporation Procédé de réticulation de gélatine et incorporation d'un matériau
EP1940249B1 (fr) * 2005-10-21 2015-06-03 DSM IP Assets B.V. Nouvelles formulations d'ingrédients actifs liposolubles ayant une biodisponibilité élevée
US20190099371A1 (en) * 2016-03-24 2019-04-04 Basf Se Multiphase active substance preparations
WO2019185900A1 (fr) 2018-03-29 2019-10-03 Dsm Ip Assets B.V. Procédé de production de chroman-6-ols à chaînes latérales courtes
WO2019185942A1 (fr) 2018-03-29 2019-10-03 Dsm Ip Assets B.V. Utilisation de tocotriénols en tant qu'antioxydants
WO2019185888A1 (fr) 2018-03-29 2019-10-03 Dsm Ip Assets B.V. Nouvelle utilisation de tocophérols
WO2019185940A1 (fr) 2018-03-29 2019-10-03 Dsm Ip Assets B.V. Utilisation de chromanols jumelés en tant qu'antioxydants
WO2019185894A1 (fr) 2018-03-29 2019-10-03 Dsm Ip Assets B.V. Nouvelle utilisation de chroman-6-ols substitués
WO2019185904A1 (fr) 2018-03-29 2019-10-03 Dsm Ip Assets B.V. Chroman-6-ols à chaîne latérale lipophile étendue en position 2, leur fabrication et leur utilisation
WO2019185898A1 (fr) 2018-03-29 2019-10-03 Dsm Ip Assets B.V. Nouvelle utilisation des 2h-chromènes substitués et de leurs dérivés
WO2019185938A2 (fr) 2018-03-29 2019-10-03 Dsm Ip Assets B.V. Nouvelle utilisation des chroman-6-ols substitués à chaînes latérales lipophiles étendues

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991006292A1 (fr) 1989-11-02 1991-05-16 Danochemo A/S Procede de preparation d'un solide hydrophobe ou aerophile dispersible dans l'eau
US5460823A (en) * 1989-11-02 1995-10-24 Danochemo A/S Process of preparing a water dispersible hydrophobic or aerophilic solid
EP0494417A2 (fr) 1991-01-10 1992-07-15 Basf Corporation Procédé de réticulation de gélatine et incorporation d'un matériau
EP1940249B1 (fr) * 2005-10-21 2015-06-03 DSM IP Assets B.V. Nouvelles formulations d'ingrédients actifs liposolubles ayant une biodisponibilité élevée
US20190099371A1 (en) * 2016-03-24 2019-04-04 Basf Se Multiphase active substance preparations
WO2019185942A1 (fr) 2018-03-29 2019-10-03 Dsm Ip Assets B.V. Utilisation de tocotriénols en tant qu'antioxydants
WO2019185900A1 (fr) 2018-03-29 2019-10-03 Dsm Ip Assets B.V. Procédé de production de chroman-6-ols à chaînes latérales courtes
WO2019185888A1 (fr) 2018-03-29 2019-10-03 Dsm Ip Assets B.V. Nouvelle utilisation de tocophérols
WO2019185940A1 (fr) 2018-03-29 2019-10-03 Dsm Ip Assets B.V. Utilisation de chromanols jumelés en tant qu'antioxydants
WO2019185894A1 (fr) 2018-03-29 2019-10-03 Dsm Ip Assets B.V. Nouvelle utilisation de chroman-6-ols substitués
WO2019185904A1 (fr) 2018-03-29 2019-10-03 Dsm Ip Assets B.V. Chroman-6-ols à chaîne latérale lipophile étendue en position 2, leur fabrication et leur utilisation
WO2019185898A1 (fr) 2018-03-29 2019-10-03 Dsm Ip Assets B.V. Nouvelle utilisation des 2h-chromènes substitués et de leurs dérivés
WO2019185938A2 (fr) 2018-03-29 2019-10-03 Dsm Ip Assets B.V. Nouvelle utilisation des chroman-6-ols substitués à chaînes latérales lipophiles étendues

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
BASF: "BASF launches new vitamin A product line", 18 July 2017 (2017-07-18), XP055889222, Retrieved from the Internet <URL:https://www.efeedlink.com/contents/07-18-2017/81c924ee-5968-4190-abf9-429cb30dfa4a-0020.html> [retrieved on 20220208] *
BASF: "Lutavit A 1000 NXT", 25 June 2020 (2020-06-25), XP055889211, Retrieved from the Internet <URL:https://www.basf.com/us/documents/en/general-business-topics/cfia-labels/pdf/Label_983737_Lutavit_A_1000_NXT_25Jun20-CFIA.PDFPDF> [retrieved on 20220208] *
BASF: "Safety data sheet SECTION 1: Identification of the substance/mixture and of the company/undertaking Lutavit A 1000 NXT", 3 July 2017 (2017-07-03), XP055888369, Retrieved from the Internet <URL:https://documents.basf.com/10cf782d7e90d3edd345834b3d49553362444a7c/MSDS_000000000030652838_en.pdf?response-content-disposition=inline> [retrieved on 20220208] *
PAN YANG ET AL., ANIMALS, vol. 9, 2019, pages 1154

Similar Documents

Publication Publication Date Title
ES2390625T3 (es) Gránulos de enzima
US10729159B2 (en) Method of feeding an animal
CN110944517A (zh) 动物饲料补充剂
Harper et al. Assessment of a hydrated sodium calcium aluminosilicate agent and antioxidant blend for mitigation of aflatoxin-induced physiological alterations in pigs
BR112020000084A2 (pt) comprimidos compactados
SE523209C2 (sv) Förfarande för att reducera metanbildningen från matspjälkningsaktiviteter hos djur
Küçükyilmaz et al. Evaluation of the boron and phytase, alone or in combination, in broiler diets
WO2022112586A1 (fr) Nouvelles formulations sans sucre, leur production et leur utilisation
WO2022112587A1 (fr) Nouvelles formulations à teneur réduite en antioxydant, leur production et leur utilisation
WO2022112585A1 (fr) Nouvelles formulations sans sucre, leur fabrication et leur utilisation
Haščík et al. Oxidative stability of chicken meat after pollen extract application in their diet.
EP4250959A1 (fr) Nouvelles formulations à teneur réduite en antioxydant, leur fabrication et leur utilisation
WO2022078924A1 (fr) Nouveaux additifs alimentaires de vitamines liposolubles
Ürüşan Hepatoprotective effect of Artichoke (Cynara scolymus) in laying hens
WO2022129435A1 (fr) Succédané de lait comportant des formulations d&#39;origine non animale de vitamines liposolubles
Hoan et al. Effect of supplementation of green tea extract on blood corticosterone concentration and growth performance in heat-stressed broiler
Ogbuewu Effects of mycotoxins in animal nutrition: a review
Pietrzak et al. The influence of protein-xanthophyll concentrate of alfalfa on growth performance and carcass value of growing-finishing pigs
WO2022129433A1 (fr) Lait de remplacement comprenant des formulations sans matière animale de vitamines liposolubles
Xavier et al. Variation in quality of newly hatched chicks from Japanese breeder quail fed guava extract
EFSA Panel on Additives and Products or Substances used in Animal Feed (FEEDAP) Scientific Opinion on the safety and efficacy of citric acid when used as a technological additive (acidity regulator) for all animal species
EP4040982A1 (fr) Nouveaux additifs alimentaires de vitamines liposolubles
Ondrej et al. The effect of hempseed cakes on broiler chickens peroformance parameters
RU2798969C2 (ru) Способ кормления животного
RU2602199C1 (ru) Способ купирования теплового стресса кур

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 21816094

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 21816094

Country of ref document: EP

Kind code of ref document: A1