WO2021069733A1 - Nouveaux additifs alimentaires de caroténoïdes - Google Patents

Nouveaux additifs alimentaires de caroténoïdes Download PDF

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Publication number
WO2021069733A1
WO2021069733A1 PCT/EP2020/078565 EP2020078565W WO2021069733A1 WO 2021069733 A1 WO2021069733 A1 WO 2021069733A1 EP 2020078565 W EP2020078565 W EP 2020078565W WO 2021069733 A1 WO2021069733 A1 WO 2021069733A1
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Prior art keywords
ranging
weight
feed additive
astaxanthin
hexose
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PCT/EP2020/078565
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English (en)
Inventor
Sebastien RIDER
Christian Schaefer
Roland SCHEX
Viviane VERLHAC
Thomas Zwick
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Dsm Ip Assets B.V.
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Priority to EP20789593.9A priority Critical patent/EP4040980A1/fr
Priority to AU2020365042A priority patent/AU2020365042A1/en
Priority to CN202080070994.8A priority patent/CN114513963A/zh
Publication of WO2021069733A1 publication Critical patent/WO2021069733A1/fr

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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
    • A23K50/80—Feeding-stuffs specially adapted for particular animals for aquatic animals, e.g. fish, crustaceans or molluscs
    • 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
    • A23K20/105—Aliphatic or alicyclic compounds
    • 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
    • A23K20/116—Heterocyclic compounds
    • A23K20/132—Heterocyclic compounds containing only one nitrogen as hetero atom
    • 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
    • A23K20/163—Sugars; Polysaccharides
    • 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
    • A23K20/179—Colouring agents, e.g. pigmenting or dyeing agents

Definitions

  • the present invention is directed to a feed additive comprising a) at least a carotenoid in an amount ranging from 0.5 to 25 weight-%; b) at least a lignosulfonate in an amount ranging from 35 to 60 weight-%; and c) at least a compound selected from hexose-dimers, modified hexose-dimers, hexose-oligomers, modified hexose-oligomers, hexose-polymers, modified hexose-polymers, and any mixture thereof in an amount ranging from 5 to 25 weight-%, whereby further optionally at least one hexose may be present; d) at least an antioxidant in an amount ranging from 0 to 20 weight-%; e) at least an absorbent in an amount ranging from 1 to 20 weight-%; and residual moisture in an amount ranging from 0 to 10 weight-%; wherein the lignosulfonate b) and the compound
  • Carotenoids are organic pigments ranging in color from yellow to red that are naturally produced by certain bioorganisms, including photosynthetic organisms (e.g., plants, algae, bacteria such as cyanobacteria), and some fungi. Carotenoids are responsible for the orange color of carrots, as well as the pink color in flamingos and salmon, and the red color in lobsters and shrimp. Animals, however, cannot produce carotenoids and must receive them through their diet.
  • photosynthetic organisms e.g., plants, algae, bacteria such as cyanobacteria
  • Carotenoids are responsible for the orange color of carrots, as well as the pink color in flamingos and salmon, and the red color in lobsters and shrimp. Animals, however, cannot produce carotenoids and must receive them through their diet.
  • Carotenoid pigments e.g. ⁇ -carotene and astaxanthin
  • Carotenoid pigments are used industrially as ingredients for food and feed stocks, both serving a nutritional function and enhancing consumer acceptability.
  • astaxanthin is widely used in salmon aquaculture to provide the pink/red pigmentation characteristic of their wild counterparts.
  • Some carotenoids provide potential health benefits, for example as vitamin A precursors or antioxidants.
  • Some carotenoids such as ⁇ - carotene, lycopene, astaxanthin, zeaxanthin and lutein are currently sold as nutritional supplements.
  • Astaxanthin is a red to reddish-orange pigment and is produced naturally in the freshwater microalgae Haematococcus pluvialis and the yeast fungus Xanthophyllomyces dendrorhous (also known as Phaffia).
  • the algae is stressed by lack of nutrients, increased salinity, or excessive sunshine, it produces astaxanthin.
  • Animals who feed on the algae such as red sea bream, flamingos and crustaceans (ie. shrimp, krill, crab, lobster and crayfish) and carnivorous fish consuming small crustaceans, subsequently reflect the red to reddish-orange astaxanthin pigmentation to various degrees.
  • feed additive comprising at least a carotenoid or a feed comprising such feed additive which results in a desired level of muscle retention in the animal it is administered to.
  • Aquatic animals in the context of the present invention encompass crustaceae and fish, preferably farmed Crustacea such as shrimp and carnivorous species of farmed fish such as salmons, rainbow trout, brown trout ( Salmo trutta) and gilthead seabream.
  • a feed additive comprising astaxanthin or any derivative thereof which results in a muscle retention of at least 7% of astaxanthin in salmon; i.e. 7% of the astaxanthin amount that has been ingested by the salmon is retained in the muscle.
  • a feed additive comprising astaxanthin or any derivative thereof which results in a muscle retention of at least 13%, preferably of at least 14%, of astaxanthin in rainbow trout; i.e. at least 13%, preferably at least 14%, of the astaxanthin amount that has been ingested by the rainbow trout is retained in the muscle.
  • feed additive comprising astaxanthin or any derivative thereof which results in the desired astaxanthin level in shrimp, to which feed is administered which comprises the feed additive of the present invention.
  • feed additive which is “animal-free” meaning that it does not comprise any ingredient from animal origin.
  • a feed additive comprising a) at least a carotenoid in an amount ranging from 0.5 to 25 weight-%; b) at least a lignosulfonate in an amount ranging from 35 to 60 weight-%; and c) at least a compound selected from hexose-dimers, modified hexose-dimers, hexose-oligomers, modified hexose-oligomers, hexose-polymers, modified hexose-polymers, and any mixture thereof in an amount ranging from 5 to 25 weight-%, whereby further optionally at least one hexose may be present; d) at least an antioxidant in an amount ranging from 0 to 20 weight-%; e) at least an absorbent in an amount ranging from 1 to 20 weight-%; and residual moisture in an amount ranging from 0 to 10 weight-%; wherein the lignosulfonate
  • the feed additive of the present invention is resulting in the desired muscle retention level in the animal to which it is administered in form of a feed comprising such feed additive according to the present invention.
  • the feed additive of the present invention is especially resulting in the desired astaxanthin level of 7 mg/kg in salmon, to which feed is administered which comprises the feed additive of the present invention. Furthermore, the feed additive of the present invention shows the necessary stability which is proven by the stress tests and per-se stability tests performed (results shown in Tables 7, 8 and 10-12).That means that the feed additives according to the present invention, especially those containing astaxanthin or a derivative thereof, are stable for at least 1 month, preferably for at least 2 months, more preferably for at least 3 months, most preferably for at least 6 months at 40° C and 75% relative humidity, "stable” means that the loss of the carotenoid due to degradation etc. is less than 7 weight-% on the basis of the initial concentration, preferably less than 5 weight-%.
  • the feed additive of the present invention shows a low filtration residue (see Tables 6 and 13).
  • the filtration residue is used to assess the quality of the feed additive by re-dispersing ca. 1 g of feed additive in water, filtering it through a filter paper (pore size 4-12 ⁇ m) and a filter aid, and washing the filter with water. The fraction remaining in the filter is recovered and determined by spectrophotometry (K. Schiedt and S. Liaaen-Jensen, Isolation and Analysis. In: G. Britton, S. Liaaen- Jensen, H. Pfander (Eds.). Carotenoids, Volume 1A: Isolation and Analysis;1995 Birkhauser Verlag Basel, Switzerland).
  • the feed additives of the present invention do not comprise beeswax which is in discussion because of increasing levels of pesticide residues.
  • the lignosulfonate(s) and the compound c) form a dense and glassy matrix as mixture of compounds of varying molecular size and featuring different functional groups.
  • encapsulated means that the carotenoid is embedded in the matrix of lignosulfonate(s) b) and the compound c) and thereby protected against oxidation and degradation.
  • the precursor of the feed additive i.e. the dispersion obtained after having performed step iv) of the process for the manufacture of the feed additive according to the present invention, forms an oil-in-water type dispersion whereby the carotenoid is the oil being located in the internal phase and the lignosulfonate acts as emulsifier.
  • the compound c) is the filler and additional emulsifier in the matrix contributing to its stability.
  • the matrix comprising the carotenoid is coated by the absorbent.
  • “Coated” in the context of the present invention means that the absorbent surrounds the matrix.
  • the single compounds of the feed additive according to the present invention and their amounts may be determined as follows:
  • the carotenoid can e.g. be extracted and analyzed by HPLC-DAD (High Performance Liquid Chromatography Diode Array Detection) or HPLC-FL (High Performance Liquid Chromatography-Fluorescence Detection) according to the following published method:
  • the lignosulfonate(s) can be spectrophotometrically determined in formulations e.g. according to a procedure disclosed by G. Jayne and E. Pohl in Das Textil, 1967, 21, Vol. 10 A, pages 645-653 ("Nach Stamm der Ligninsulfonklare in grosser Versternung (Abciesser von Sulfitzellstoff-Fabriken)”).
  • Modified hexose-polymers such as e.g. OSA starches can be qualitatively identified using wet chemistry methods such as e.g. described in the monograph "Modified Starches” (FAO JECFA Monograph 16). The quantification of the OSA-starches can be performed by polarimetry (see e.g. Gorden A. Mitchel, Methods of Starch Analysis, 1990, 42, pages 131-134). Mixtures of hexoses, hexose-dimers, hexose-oligomers and/or hexose-polymers; i.e. e.g. starch hydrolysates can be analyzed by size-exclusion chromatography; see e.g.
  • Hexoses and hexose-dimers i.e. e.g. sugars such as sucrose
  • HPLC High Performance Liquid Chromatography
  • Rl Refractive Index
  • pulsed amperometric detection see e.g.
  • Antioxidants can be analyzed by HPLC-DAD/FL (High Performance Liquid Chromatography- Diode Array Detection/ Fluorescence Detection) as e.g. disclosed by Paula Becker Pertuzatti, Marla Sclorla, Andressa Carolina Jacques, Milene Teixeira Barcia, Rui Carlos Zambiazi, in LWT - Food Science and Technology 2015, Volume 64, Issue 1, pages 259-263 (“Carotenoids, tocopherols and ascorbic acid content in yellow passion fruit (Passiflora edulis) grown under different cultivation systems”).
  • HPLC-DAD/FL High Performance Liquid Chromatography- Diode Array Detection/ Fluorescence Detection
  • the coating with the absorbent can be qualitatively characterized using microscopic techniques coupled with spectroscopic techniques such as FTIR (Fourier Transformation Infrared) for identification of starches and X-ray fluorescence for silicium dioxide; see e.g. P.V. Kowsik, N. Mazumder, Microsc. Res. Tech. 2018, 81, pages 1533-1540 ("Structural and chemical characterization of rice and potato starch granules using microscopy and spectroscopy.”) and M. Mutsuga, K. Sato, Y. Hirahara, Y. Kawamura, Food Addit. Contam. Part A Chem. Anal. Control Expo. Risk Assess. 2011, 28(4), pages 423-427 (“Analytical methods for SiO 2 and other inorganic oxides in titanium dioxide or certain silicates for food additive specifications”). For the determination of the other absorbents corresponding analytical methods are known to the person skilled in the art.
  • FTIR Fastier Transformation Infrared
  • examples of the carotenoid include naturally-occurring carotenoids obtained by extraction from natural sources such as plant materials as well as synthetic carotenoids obtained by conventional methods such as chemical synthesis or fermentation.
  • examples of carotenoids include hydrocarbons (carotenes) and oxidized alcohol derivatives thereof (xanthophylls).
  • carotenoids examples include actinioerythrol, astaxanthin, bixin, canthaxanthin, capsanthin, capsorbin, b-s'-apo-carotenal (apocarotenal), p-12'-apo-carotenal, b- 4’-apo-carotenal, ethyl-8'-apo- ⁇ -caroten-8’-oate, ⁇ -carotene, ⁇ -carotene, ⁇ - carotene, ⁇ -cryptoxanthin, ⁇ -cryptoxanthin, lutein, lycopene, violerythrin, zeaxanthin, citranaxanthin, phytoene, phytofluene, crocin, crocetin, rubixanthin, violaxanthin, rhodoxanthin, and any mixture thereof, as well as derivatives such as esters (e.g. fatty acid esters) of hydroxyl- or carboxyl-containing compounds selected from
  • carotenoids already being used in feed may be used in the feed additive according to the present invention.
  • These carotenoids may be used for pigmentation, especially for coloring the skin and fat of poultry, for egg yolk pigmentation or for the pigmentation of aquatic animals such as e.g. fish and crustaceae.
  • Preferred examples of such carotenoids are: astaxanthin and its derivatives such as fatty acid esters thereof, canthaxanthin, ethyl-8’-apo- ⁇ - caroten-8’-oate (“apo-ester”), ⁇ -carotene, lutein and its derivatives such as fatty acid esters thereof, as well as any mixture thereof.
  • Derivatives are structural analogs of a compound that are derived from a similar compound by a chemical reaction.
  • the term “derivatives” especially encompasses esters, preferably fatty acid esters.
  • the fatty acids in these esters are preferably linear or branched, saturated or unsaturated fatty acids having 8 to 22 carbon atoms.
  • Carotenoids particularly preferably used in the present invention include the free form of astaxanthin and/or its derivatives such as esters of astaxanthin (hereinafter, these are generically referred to as "astaxanthins").
  • Astaxanthin diesters as disclosed in WO 2003/066583 could also be used in the feed additives of the present invention, i.e. compounds of the following formula (I) wherein R and R* are independently from each other -NH-CH(R 1 )-COOR 2 or OR 3 or -(Y) n -Z, whereby R 1 signifies hydrogen or the residue of a protein-forming amino acid, R 2 signifies C 1-6 -alkyl or C 3-8 -cycloalkyl, R 3 signifies C 1-12 -alkyl or C 3-8 -cycloalkyl,
  • Y signifies C 1-7 -alkylene or C 2-7 -alkenylene
  • n signifies 0 or 1
  • —COR 5 with R 5 being hydrogen or C 1-6 -alkyl, or — CH 2 N'(CH 3 ) 3 X- with X- being a halogen ion
  • any alkyl or alkenyl group containing three or more carbon atoms can be straight chain or branched.
  • the alkylene group can be for example methylene or di-, tri-, tetra-, penta-, hexa- or heptamethylene, or, respectively, ethylidene, propylidene (ethylmethylene), 1- or 2-methyl substituted ethylene and further mono- or multi- branched alkylene groups containing altogether up to seven carbon atoms.
  • Any aryl group (a significance of Z or of R 6 in the group — 0— COR 6 signified by Z when n is 1) can be unsubstituted phenyl, naphthyl or a further multiring aromatic hydrocarbon group, or such a group featuring one or more substituents, particularly those substituents selected from C 1-4 -alkyl, C 1-4 -alkoxy, halogen and benzyloxy.
  • Halogen indicates fluorine, chlorine, bromine or iodide.
  • substituted phenyl groups are p-tolyl, 3-methoxyphenyl, 4-methoxyphenyl, 2,5- dimethoxyphenyl, 3,4-dimethoxyphenyl and 4-benzyloxyphenyl.
  • heteroaryl also a significance of Z or of R 6 in the group — O- (CO)R 6 , means a heterocyclic group of aromatic character featuring as ring member(s) one or more heteroatoms selected from oxygen, sulphur and nitrogen.
  • heteroaryl groups are 2- or 3-furyl, 2- or 3-thienyl and 4-pyridyl.
  • the heteroaryl groups can be unsubstituted or substituted by one or more substituents as indicated hereinabove for the substituted aryl groups.
  • the expression "residue of a protein-forming amino acid” (the significance of R 1 when not signifying hydrogen), this means that the group -NH- CH(R 1 )-COOR 2 in which R1 has this significance is derived from any amino acid H 2 N- CH(R 1 )-COOH, R 1 signifying the variable part of the amino acid molecule.
  • the amino acid is e.g. glycine
  • the group signifies -NH-CH 2 -COOR 2 , R 1 being hydrogen and R 2 being any C 1-6 -alkyl or C 3-8 -cycloalkyl group.
  • the group signifies -NH-CH(C 6 H 5 )-COOR 2 and phenyl (C 6 H 5 ), and -NH- CH(CH 2 CH 2 SCH 3 )-COOR 2 and 2-methylthioethyl (CH 2 CH 2 SCH 3 ), respectively.
  • halogen ion X- can be a fluoride, chloride, bromide or iodide ion, preferably a chloride ion, Cl-.
  • the astaxanthin derivatives of formula (I) can be in any possible isomeric form or in the form of mixtures of isomers, e.g. racemate mixtures.
  • the six astaxanthin derivatives astaxanthin-diethyldicarbonate, -dimethyldi-succinate, - diethyldisuccinate, -dinicotinate, -dimethoxyacetate and -di-[(2-thienyl)-acetate] are especially preferred ones.
  • Astaxanthin monoesters with the groups as given above are also encompassed by the expression "astaxanthin derivatives”.
  • Astaxanthin has three isomers: 3S,3S'-form, 3S,3R’-form (meso form), and 3R,3R’-form depending on the steric configuration of the hydroxyl group at the 3(3') -position of the ring structures present at both ends of the molecule. Astaxanthin also has cis and trans geometrical isomers with respect to the conjugated double bond system of the polyene chain at the center of the molecule. Examples include the 9-cis isomer, the 13-cis isomer, 15-cis isomer and the all-E isomer. This also applies for the astaxanthin derivatives.
  • the hydroxyl group at the 3(3’)-position can form an ester with a fatty acid.
  • astaxanthins obtained from krill contain a relatively large amount of a diester having two fatty acids bounded thereto.
  • Astaxanthin obtained from Haematococcus pluvialis, in which astaxanthin is in the 3S,3S’-form contain a relatively large amount of a monoester having one fatty acid bonded thereto.
  • Astaxanthin obtained from Phaffia Rhodozymo is the 3R,3R'-form which has a structure reverse to the 3S,3S'-form generally found in nature. This is also present in the non-ester form without forming any ester with a fatty acid, in other words, in the free form.
  • the feed additive of the present invention may contain an astaxanthin-containing oil, which is separated or extracted from astaxanthin-containing natural products.
  • an astaxanthin-containing oil include extracts obtained from cultures of a red yeast, Phaffia, a green alga Haematococcus, marine bacteria, or other organisms; and extracts from antarctic krill or the like.
  • the astaxanthin that can be used in the present invention may be the extracts mentioned above, products obtained by appropriate purification of the extracts as needed, or chemically synthesized products. Chemically synthesized astaxanthin as commercially available from DSM Nutritional Products AG (CH) is especially preferred.
  • CH DSM Nutritional Products AG
  • the amount of astaxanthin in the feed additive of the present invention is calculated directly, but the amount of a fatty acid ester of astaxanthin is calculated in terms of the free form of astaxanthin.
  • the amount of the carotenoid is chosen in such a way so that its final amount in the feed additive is preferably ranging from 0.5 to 25 weight-%, more preferably its final amount is ranging from 2.0 to 20 weight-%, even more preferably its final amount is ranging from 5.0 to 20 weight-%, most preferably its final amount is ranging from 8 to 16 weight-%, based on the total weight of the dry matter of the feed additive.
  • its final amount in the feed additive is preferably ranging from 0.5 to 25 weight-%, more preferably its final amount is ranging from 2.0 to 20 weight-%, even more preferably its final amount is ranging from 5.0 to 20 weight-%, most preferably its final amount is ranging from 8 to 16 weight-%, based on the total weight of the dry matter of the feed additive.
  • the lignosulfonate(s) present in the feed additives according to the present invention are especially industrially produced products which contain lignosulfonates having the widest variety of cations. Sodium, calcium, magnesium and ammonium lignosulfonate are especially preferred.
  • a feed additive according to the present invention can contain a single lignosulfonate or a mixture of several lignosulfonates as ingredient b).
  • the lignosulfonate(s) present in the feed additives according to the present invention can be part of an industrially produced product which contains further components in addition to the lignosulfonate(s).
  • lignin occurs together with cellulose in plants, especially in wood.
  • Wood depending on the type, contains about 16 to 37 weight-% of lignin.
  • lignin consists of irregular polymers of methoxylated phenylpropane monomers (p-coumaryl alcohol, coniferyl alcohol, sinapyl alcohol etc.) having a molecular weight estimated to be at least 20 kD.
  • p-coumaryl alcohol, coniferyl alcohol, sinapyl alcohol etc. having a molecular weight estimated to be at least 20 kD.
  • lignosulfonate also known as “sulfite lignin”.
  • the decomposition of wood is also achieved by treatingthe wood with sodium hydroxide and disodium tetrasulfide (the "Kraft process”).
  • the lignin obtained in this process is referred to as “Kraft lignin” or “sulfate lignin” and is not water-soluble at neutral pH.
  • organic solvents e.g. alcohol, also mixed with water, for the decomposition of wood, and the thus-produced lignin is referred to as “organosolv lignin”.
  • organic solvents e.g. alcohol
  • organosolv lignin organic solvents
  • This form of lignin is likewise not water-soluble.
  • lignosulfonates and Kraft lignins are commercially available.
  • lignosulfonate-containing solution is concentrated to about 50% solid content and sold in this form.
  • Most producers also offer pulverous products which have been obtained by spray-drying the solutions, and these solid forms also contain various saccharides in considerable amounts in addition to lignin.
  • Some producers manufacture lignosulfonates having a relatively high content of lignosulfonate(s) from the primary (crude) lignosulfonates by enzymatic removal of the saccharides and, if necessary, by purification, for example by ultracentrifugation.
  • the Kraft lignins which are also offered, can be sulfonated in order to achieve water- solubility and the sulfonation products are suitable as lignosulfonates for use in the preparations in accordance with the invention.
  • Commercial lignosulfonate products typically consist of about 40-90% lignosulfonate and smaller amounts of various saccharides, ash, carbohydrates, acetates, formates, resins etc., with the composition depending very much on the quality of the wood which is used.
  • Such water-soluble lignosulfonate products are also suitable for use in the feed additives in accordance with the invention.
  • the crude products having a relatively high content of saccharides and additional byproducts but also the aforementioned purified lignosulfonate(s) can be used in the feed additives in accordance with the invention, provided that such lignosulfonate(s) are water- soluble or at least water-dispersible.
  • Preferred examples of well-suited lignosulfonate(s) are: sodium lignosulfonate, ammonium lignosulfonate, magnesium and calcium lignosulfonate.
  • Sodium lignosulfonate and calcium lignosulfonate are especially preferred. Most preferred is calcium lignosulfonate.
  • lignosulfonate(s) Suppliers of lignosulfonate(s) 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.
  • Especially suitable de-sugared calcium lignosulfonate is available from Borregaard Industries Limited, Norway under the tradenames Borrebright CY22P, Borresperse Na220 and Borrement CA120, whereby Borrebright CY22P is especially preferred.
  • This is manufactured by cutting spruce timer into chips and feeding it into a digester together with cooking calcium bisulfite solution.
  • the lignin in the wood is depolymerized and sulfonated, which makes water-soluble lignosulfonates.
  • the sulfite liquor contains calcium lignosulfonate and sugars.
  • the sulfite liquor (calcium lignosulfonate and sugars) is separated from the cellulose pulp by filtration.
  • the sulfite lye is concentrated to about 53% in an evaporation plant.
  • the concentrated liquor is fed into a spray dryer to produce lignosulfonate powder (inlet temperature ranging from 200 to 250°C).
  • the amount of the lignosulfonate(s) is chosen in such a way so that its final amount in the feed additive is preferably ranging from 35 to 60 weight-%, more preferably its final amount is ranging from 37 to 57 weight-%, even more preferably its final amount is ranging from 40 to 55 weight-%, most preferably its final amount is ranging from 40 to 54 weight-%, based on the total weight of the dry matter of the feed additive.
  • the weight ratio of the lignosulfonate(s) b) to the carotenoid(s) a) is ranging from 1:1 to 15:1, preferably ranging from 1:1 to 10:1, more preferably ranging from 2:1 to 7:1 , even more preferably ranging from 3:1 to 6:1, most preferably ranging from 3.5:1 to 5.2:1.
  • the weight ratio of the compound(s) c) to the lignosulfonate(s) b) is ranging from 2:1 to 1:10, preferably ranging from 1:1 to 1:7, more preferably ranging from 1:1.5 to 1:6, most preferably ranging from 1:2 to 1:5.5.
  • the compound c) is selected from hexose-dimers, modified hexose-dimers, hexose oligomers, modified hexose oligomers, hexose-polymers, modified hexose- polymers and any mixture thereof.
  • a hexose may also be present. That means that mixtures of hexoses and hexose-dimers are also encompassed.
  • An example of a mixture of hexose and hexose-dimers is invert sugar (glucose + fructose + sucrose).
  • a hexose is a monosaccharide with six carbon atoms. Hexoses are classified by functional group, with aldohexoses having an aldehyde at position 1, and ketohexoses having a ketone at position 2.
  • the compound c) is selected from aldohexose-ketohexose-dimers, aldohexose-oligomers or modified aldohexose polymers or any mixture thereof.
  • the hexose in the hexose-dimers may be one single hexose or two hexoses being distinct from each other.
  • hexose-dimers are sucrose (glucose-fructose- dimer), lactose (glucose-galactose-dimer), maltose (glucose-dimer with an a-(1-4)- linkage), isomaltose (glucose-dimer with an ⁇ -(1-6)-linkage), trehalose (glucose- dimer with an ⁇ -(1-1)-linkage) and nigerose (glucose-dimer with an ⁇ -(1-3)-linkage), as well as any mixture thereof.
  • sucrose glucose-fructose-dimer
  • lactose lactose
  • maltose glucose-dimer with an a-(1-4)- linkage
  • the hexose in the hexose-oligomers may be one single hexose or several hexoses being distinct from each other.
  • the hexose is glucose.
  • More preferred examples of hexose-oligomers are hydrolysed starch products such as glucose syrups, dried glucose syrups or dextrins. Such glucose syrups, dried glucose syrups and dextrins are classified according to their “dextrose equivalents" and may further contain hexoses, hexose-dimers and hexose polymers.
  • Dextrose is a synonym for "glucose”.
  • DE denotes the degree of hydrolysis and is a measure of the amount of reducing sugar calculated as D-glucose based on dry weight; the scale is based on native starch having a DE close to 0 and glucose having a DE of 100.
  • Maltodextrin is a dextrin with a DE in the range of from 3 to 20; hydrolysed starch products with a DE > 20 are called “glucose syrups” or “dried glucose syrups” - depending on their water content. "Glucose syrups” or “dried glucose syrups” may be used in form of powders, micro-granulates or granulates. Glucose syrups consist in general of a mixture of glucose, maltose and oligo- and polysaccharides with varying amounts of these ingredients.
  • hexose-oligomers that also contain hexoses and hexose- dimers are e.g. commercially available under the tradenames Glucidex 21 (from Roquette), Glucidex IT 47 (from Roquette), Dextrose Monohydrate ST (from Roquette), Sirodex 331 (from Tate & Lyle), Glucamyl F 452 (from Tate & Lyle) and Raftisweet I 50/75/35 (from Lebbe Sugar Specialties), whereby Glucidex 21 and Glucidex 47 are especially preferred.
  • the hexose in the hexose-polymers and modified hexose-polymers may be one single hexose or a mixture of many hexoses.
  • Preferably one hexose or two hexoses being distinct from each other are present in the hexose-polymers or modified hexose-polymers of the present invention.
  • OSA-starches modified food starches
  • OSA-starches modified with octenyl succinic acid
  • the most preferred compounds c) are starch hydrolysates, such as e.g. dried glucose syrups and dextrins, with a DE ranging from 10 to 50, more preferably with a DE ranging from 15 to 40, even more preferably with a DE ranging from 15 to 30, most preferably with a DE ranging from 15 to 25.
  • a DE ranging from 10 to 50 more preferably with a DE ranging from 15 to 40, even more preferably with a DE ranging from 15 to 30, most preferably with a DE ranging from 15 to 25.
  • starch hydrolysates are dried glucose syrups as e.g. Glucidex 21 and Glucidex IT47, and dextrins such as Yellow dextrin. Most preferred examples are also their mixtures with modified food starches, whereby a weight ratio of dried glucose syrup or dextrin to modified food starch ranging from 1:3 to 3:1, preferably from 1:2 to 2:1, most preferably of 1:1 is especially preferred. More details are given below.
  • Glucidex 21 is a dried glucose syrup with a DE ranging from 20 to 23 in the form of a fine powder with at least 50% of the particles being greater than 40 ⁇ m and at most 10% of the particles being greater than 250 pm. Glucidex 21 contains 3% glucose, 7% maltose and 90% oligo- and polysaccharides.
  • Glucidex IT 47 is a dried glucose syrup with a DE ranging from 43 to 47 in the form of micro-granulates with at least 95% of the particles being greater than 40 ⁇ m and at most 5% of the particles being greater than 500 pm. Glucidex IT 47 contains 5% glucose, 50% maltose and 45% oligo- and polysaccharides.
  • Further preferred compounds c) are starch hydrolysates that have a maximum amount of 10 weight% of reducing sugars, based on the total weight of the starch hydrolysate.
  • the amount of the compound c) is chosen in such a way so that its final amount in the feed additive is at least 5 weight-%, preferably its final amount is ranging from 5 to 30 weight-%, more preferably its final amount is ranging from 5 to 25 weight- %, even more preferably its final amount is ranging from 8 to 25 weight-%, most preferably its final amount is ranging from 10 to 22 weight-%, based on the total weight of the dry matter of the feed additive.
  • the compound c) is a mixture of at least 5 weight-% of a hexose oligomer such as e.g. dextrins and at least 5 weight-% of a modified hexose polymer such as e.g. modified food starch, both amounts based on the total weight of the feed additive.
  • a hexose oligomer such as e.g. dextrins
  • a modified hexose polymer such as e.g. modified food starch
  • Dextrins are a group of low-molecular-weight carbohydrates produced by the hydrolysis of starch or glycogen. Dextrins are mixtures of polymers of D-glucose units linked by ⁇ -(1 ⁇ 4) or ⁇ -(1 ⁇ 6) glycosidic bonds.
  • Dextrins can e.g. be produced from starch using enzymes like amylases or by applying dry heat under acidic conditions ("pyrolysis» or “roasting»). Dextrins produced by heat are also known as «pyrodextrins».
  • the starch hydrolyses during roasting under acidic conditions, and short-chained starch parts partially re-branch with ⁇ -(1,6) bonds to the degraded starch molecule. They have a low viscosity.
  • Yellow Dextrin from Roquette is used in the feed additives of the present invention.
  • “Modified food starch” is used in the feed additives of the present invention.
  • a modified food starch is a food starch that has been chemically modified by known methods to have a chemical structure which provides it with a hydrophilic and a lipophilic portion.
  • the modified food starch has a long hydrocarbon chain as part of its structure (preferably C5-C18).
  • At least one modified food starch is preferably used to make a feed additive of this invention, but it is possible to use a mixture of two or more different modified food starches in one feed additive.
  • modified food starches are hydrophilic and therefore do not have emulsifying capacities.
  • modified food starches are made from starches substituted by known chemical methods with hydrophobic moieties.
  • starch may be treated with cyclic dicarboxylic acid anhydrides such as succinic anhydrides, substituted with a hydrocarbon chain.
  • a particularly preferred modified food starch has the following formula (I) wherein St is a starch, R is an alkylene radical and R ' is a hydrophobic group.
  • R is a lower alkylene radical such as dimethylene or trimethylene.
  • R ' may be an alkyl or alkenyl group, preferably having 5 to 18 carbon atoms.
  • a preferred compound of formula (I) is an "OSA-starch” (starch sodium octenyl succinate).
  • the degree of substitution i.e. the number of esterified hydroxyl groups to the number of free non-esterified hydroxyl groups usually varies in a range of from 0.1% to 10%, preferably in a range of from 0.5% to 4%, more preferably in a range of from 2% to 3%.
  • the term “OSA-starch” denotes any starch from any natural source that was treated with octenyl succinic anhydride (OSA).
  • the degree of substitution i.e.
  • the number of hydroxyl groups esterified with OSA to the number of free non- esterified hydroxyl groups usually varies in a range of from 0.1% to 10%, preferably in a range of from 0.5% to 4%, more preferably in a range of from 2% to 3%.
  • "Modified food starch” is a synonym often used for OSA-starches.
  • the natural source of the starch may be corn, waxy corn, wheat, tapioca, pea and potato or synthesized.
  • OSA-starches encompasses also such starches that are commercially available e.g. from Ingredion under the tradenames HiCap 100, Capsul (octenylbutanedioate amylodextrin), Capsul HS, Purity Gum 2000, Cleargum COA1, Cleargum CO03, UNI-PURE, HYLON VII; from Ingredion and Roquette, respectively; from Cargill under the tradename C*EmCap or from Tate & Lyle.
  • HiCap 100 Capsul (octenylbutanedioate amylodextrin)
  • Capsul HS Purity Gum 2000, Cleargum COA1, Cleargum CO03, UNI-PURE, HYLON VII; from Ingredion and Roquette, respectively; from Cargill under the tradename C*EmCap or from Tate & Lyle.
  • a commercially available modified food starch such as Capsul and Capsul HS from Ingredion or Cleargum COA1 from Roquette, respectively, is used.
  • modified starches and "OSA-starches” encompass further also modified starches/OSA-starches that were partly hydrolysed enzymatically, e.g. by glycosylases (EC 3.2; see http://www.chem.qmul.ac.Uk/iubmb/enzyme/EC3.2/), as well as to modified starches/OSA-starches that were partly hydrolysed chemically by known methods (so-called acid degradation).
  • the enzymatic hydrolysis is conventionally carried out at a temperature of from about 5°C to about ⁇ 100°C, preferably at a temperature of from about 5°C to about 70°C, more preferably at a temperature of from about 20°C to about 55°C.
  • the glycosylases can be from fruit, animal origin, bacteria or fungi.
  • the glycolase may have endo-activity and/or exo-activity. Therefore, enzyme preparations of endo- and exo-glycosylases or any of their mixtures may be used.
  • the glycosylases Preferably have pectolytic and/or hemicelluloytic activity. Usually the glycosylases show also unknown side activities, but which are not critical for the manufacture of the desired product.
  • glycosylases are the commercially available enzyme preparations from the suppliers Novozymes, Genencor, AB-Enzymes, DSM Food Specialities, Amano, etc.
  • the glycosylase is added to provide a concentration of from about 0.01 to about 10 weight-%, preferably of from about 0.1 to about 1 weight-%, based on the dry weight of the modified starch/OSA-starch.
  • the enzyme is added at once.
  • the enzymatic hydrolysis may also be carried out stepwise. For instance, the glycosylase or a mixture of glycosylases is added to the incubation batch in an amount of e.g. 1 % whereupon, e.g.
  • the duration of hydrolysis may vary between about a few seconds and about 300 minutes.
  • the exact duration of the enzymatic treatment may be determined in an empirical way with respect to the desired properties of the modified starch/OSA- starch, such as emulsifying stability, emulsifying capacity, droplet size of the emulsion, depending strongly on parameters like enzyme activities, or composition of the substrate. Alternatively, it may be determined by measuring the osmolality (W. Dzwokak and S. Ziajka, Journal of food science, 1999, 64 (3) 393-395).
  • the inactivation of the glycosylase is suitably achieved by heat denaturation, e.g. by heating of the incubation batch to about 80 to 85°C for 5 to 30 minutes, especially for 5 to 10 minutes.
  • ethoxyquin is ⁇ 0.5 weight-%, preferably ⁇ 0.2 weight-%, more preferably ⁇ 0.1 weight-%, based on the total weight of the dry matter of the feed additive. Most preferably no ethoxyquin is added during the manufacture of the feed additive of the present invention. Thus, most preferably no ethoxyquin is present in the feed additive of the present invention.
  • butylated hydroxytoluene is ⁇ 0.5 weight-%, preferably ⁇ 0.2 weight-%, more preferably ⁇ 0.1 weight-%, based on the total weight of the dry matter of the feed additive. Most preferably no butylated hydroxytoluene is added during the manufacture of the feed additive of the present invention. Thus, most preferably no butylated hydroxytoluene is present in the feed additive of the present invention.
  • the feed additive may comprise an antioxidant or a mixture of antioxidants.
  • an antioxidant Preferably a mixture of a fat-soluble antioxidant and a water-soluble antioxidant is used.
  • its/their total amount is chosen in such a way so that its/their final amount in the feed additive is preferably ranging from 1 to 20 weight-%, more preferably its final amount is ranging from 2 to 15 weight-% and especially from 2 to 12 weight-%, even more preferably its final amount is ranging from 3 to 10 weight-%, most preferably its final amount is ranging from 3 to 8 weight-%, based on the total weight of the dry matter of the feed additive.
  • fat-soluble antioxidants are compounds of formula (II), wherein one of the two substituents R 1a and R 2a is C 12-21 -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 (II) as disclosed in WO 2019/185894 are the following compounds of formula (1)-(11) with "Me” being methyl:
  • 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 iso-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 C 1-5 -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 feed additives of the present invention.
  • fat-soluble antioxidants are compounds of the following formulae (VII) and (VIII) 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 (VII)/(VllI)” encompasses all possible isomers having any configuration at said centers.
  • the most preferred fat-soluble antioxidant is ⁇ -tocopherol, especially DL- a- tocopherol.
  • Water-soluble antioxidants In general any water-soluble antioxidant being allowed in feed and known to the person skilled in the art may be used.
  • Preferred examples of water-soluble antioxidants are ascorbic acid and salts thereof, such as alkali and earth alkali salts of ascorbic acid and ascorbyl-2- phosphate salts as disclosed in EP-A 972777.
  • alkali and earth alkali salts of ascorbic acid are especially preferred.
  • the most preferred water-soluble antioxidant is sodium ascorbate.
  • Most preferred antioxidants in the feed additive according to the present invention Most preferred is a mixture of ⁇ -tocopherol and sodium ascorbate, whereby a weight ratio of ⁇ -tocopherol to sodium ascorbate ranging from 5:1 to 1:5 is especially preferred, a weight ratio of ⁇ -tocopherol to sodium ascorbate ranging from 3:1 to 1:3 is more preferred, a weight ratio of ⁇ -tocopherol to sodium ascorbate ranging from 2.5:1 to 1:1 is even more preferred, a weight ratio of ⁇ -tocopherol to sodium ascorbate ranging from 2:1 to 1:1 is especially more preferred, and a weight ratio of ⁇ -tocopherol to sodium ascorbate of 2:1 is most preferred.
  • composition of such a feed additive is shown in the following Table 1, where the ingredients and their amounts are given. The amounts are given in weight-% and are based on the total weight of the feed ingredient comprising an absorbent. The amounts of all ingredients sum up to a total weight of 100%.
  • the weight ratio of the compound(s) c) to the lignosulfonate(s) b) is ranging from 2:1 to 1:10, preferably ranging from 1:1 to 1:7, more preferably ranging from 1:1.5 to 1:6, most preferably ranging from 1:2 to 1:5.5.
  • a preferred feed additive is one, wherein the total amount of the compounds a) to d) is at least 90 weight-%, preferably at least 95 weight-%, preferably at least 97 weight-%, based on the total weight of the dry matter of the feed additive without the weight of the absorbent.
  • Table 1 Composition of a solid feed additive according to the present invention, whereby the feed additive comprises an absorbent. All amounts are based on the total weight of said feed additive.
  • the feed additives of the present invention do not comprise beeswax which is in discussion because of increasing levels of pesticide residues.
  • compositions of preferred solid feed additives according to the present invention which comprise an absorbent, are listed in the following Tables 2-5.
  • the total amounts of all ingredients are based on the total weight of the feed additive and sum up to 100 weight-%. It is understood that each single preferred amount of one ingredient may be combined with each preferred single amount of any other ingredient.
  • the feed additives according to Table 4 are especially preferred.
  • glucose syrups can be used instead of dried glucose syrups.
  • the amount is then calculated accordingly.
  • the weight ratio of the dried glucose syrup to the lignosulfonate(s) b) is ranging from 2:1 to 1:10, preferably ranging from 1:1 to 1:7, more preferably ranging from 1:1.5 to 1:6, most preferably ranging from 1:2 to 1:5.5. Table 3
  • the weight ratio of the dextrin to the lignosulfonate(s) b) is ranging from 2:1 to 1:10, preferably ranging from 1:1 to 1:7, more preferably ranging from 1:1.5 to 1:6, most preferably ranging from 1:2 to 1:5.5.
  • the weight ratio of the dextrin and the OSA-starch to the lignosulfonate(s) b) is ranging from 2:1 to 1:10, preferably ranging from 1:1 to 1:7, more preferably ranging from 1:1.5 to 1:6, most preferably ranging from 1:2 to 1:5.5.
  • the weight ratio of the hexose-dimer to the lignosulfonate(s) b) is ranging from 2:1 to 1:10, preferably ranging from 1:1 to 1:7, more preferably ranging from 1:1.5 to 1:6, most preferably ranging from 1:2 to 1:5.5..
  • feed additives wherein the total amount of the compounds a) to d) is at least 90 weight-%, preferably at least 95 weight-%, preferably at least 97 weight-%, based on the total weight of the feed additive excluding the absorbent.
  • the amounts of their ingredients a) to d) have to be adjusted accordingly to obtain feed additives with the same relative amounts of the single ingredients a) to d) of the feed additives (see also Tables 1-5).
  • the amount of water in said liquid feed additives is preferably ranging from 30 to 60 weight-%, more preferably ranging from 35 to 55 weight-%, even more preferably ranging from 40 to 50 weight-%, most preferably ranging from 45 to 50 weight-%, based on the total weight of the liquid feed additive.
  • the present invention is also directed to a process for the manufacture of a feed additive with all the preferences as cited above comprising the following steps: i) Providing a matrix by dissolving the lignosulfonate(s) and the compound c) and optionally a water-soluble antioxidant in water; ii) Providing an active phase by dissolving the carotenoid and optionally the fat-soluble antioxidant in an organic solvent; iii) Mixing the matrix obtained in step i) and the active phase obtained in step ii) to obtain an emulsion; iv) Comminuting the droplets of the active phase in the emulsion obtained in step iii) and removing the organic solvent to obtain a dispersion; v) Drying said dispersion obtained in step iv) in presence of an absorbent to obtain the solid feed additive.
  • the feed additive may be used in liquid or in solid form.
  • the feed additive of the present invention is used in solid form.
  • step iv The single steps of the process of the manufacture of the feed additive and its precursor, i.e. the dispersion obtained after having performed step iv), are disclosed in more detail below.
  • the amounts of the lignosulfonate(s) b), the compound c) and the water-soluble antioxidant d), if present, are chosen so that the final amounts of these compounds in the resulting liquid or solid feed additive after having performed steps i) to iv) and i) to v), respectively, is as described above.
  • this step is performed at a temperature ranging from 25 to 70°C, more preferably at a temperature ranging from 30°C to 65°C, even more preferably at a temperature ranging from 40°C to 62°C, most preferably at a temperature ranging from 50° C to 60° C.
  • the amounts of the carotenoid a) and the fat-soluble antioxidant d), if present, are chosen so that the final amounts of these compounds in the resulting liquid or solid feed additive after having performed steps i) to iv) and i) to v), respectively, is as described above.
  • the amount of the organic solvent and the dissolution temperature are chosen so as to dissolve the carotenoid a) and the fat-soluble antioxidant d), if present, completely. Usually it is necessary to heat up the suspension obtained when mixing all compounds present in this step to get a solution.
  • Suitable organic solvents are methanol, ethanol, n-propanol, iso- propanol, 1-methoxy-2-butanol, 1-propoxy-2-propanol, tetrahydrofuran, acetone, dichloromethane, chloroform, tetrachloromethane, dimethyl carbonate, diethyl carbonate, propylene carbonate, ethyl formate, methyl acetate, ethyl acetate, iso- propyl acetate and methyl tert-butyl ether.
  • the temperature to which the suspension is heated up is e.g. ranging from 40 to 90° C, more preferably the temperature is ranging from 50 to 80°C.
  • this step is performed at a mixing temperature ranging from 30 to 70°C, more preferably at a mixing temperature ranging from 35 to 65°C, even more preferably at a mixing temperature ranging from 40°C to 60°C to obtain an emulsion.
  • the comminution 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.
  • the organic solvent may e.g. be removed by using a rotary evaporator or a thin film evaporator cascade. Other methods known to the person skilled in the art are also applicable.
  • the drying step is preferably carried out. Thereby the liquid form is converted into a solid form.
  • the conversion to the solid form can be achieved by any method known to the person skilled in the art where an absorbent is used, preferably by a powder-catch technique, whereby the sprayed dispersion droplets are caught by an absorbent (so-called “catch media”) such as starch and dried.
  • an absorbent such as starch and dried.
  • Suitable absorbents include corn starch, as well as starches from other botanical sources, silica, modified silica, tricalcium phosphate, calcium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate, calcium oxide, magnesium oxide, dicalcium diphosphate, calcium silicate, magnesium silicate, magnesium trisilicate, sodium aluminum silicate, talc, kaolin, calcium stearate, magnesium stearate, cellulose or mixtures thereof.
  • starch i.e. corn starch as well as starches from other botanical sources
  • silica, tricalcium phosphate and hydrophobically modified silica whereby corn starch or starches from other botanical sources such as waxy corn, wheat, tapioca, pea and potato are especially preferred.
  • the conversion to the solid form can be achieved by any method known to the person skilled in the art where no absorbent is used, e.g. by spray-drying, spray-drying in combination with fluidised bed granulation.
  • the inner phase of the feed additive according to the present invention i.e. the inner phase of the liquid feed additive after step iv) or the inner phase of the solid feed additive after step v
  • the inner phase of the feed additive according to the present invention when re-dispersed in deionized water, has a particle size ranging from 100 to 300 nm, preferably ranging from 120 to 250 nm, more preferably ranging from 130 to 230 nm, measured via dynamic light scattering using especially the particle analyzer DelsaTM Nano S (Beckmann Coulter, New Castle, DE, USA); i.e. the particles have an average diameter according to normalized intensity distribution within the ranges as given above.
  • the particle size distribution of the feed additive of the present invention is narrow, meaning that the inner phase of the solid feed additive after step v), when re-dispersed in deionized water, has a D (10%) ranging from 60 to 190 nm, preferably ranging from 70 to 180 nm, more preferably ranging from 80 to 170 nm, even more preferably ranging from 90 to 160 nm, most preferably ranging from 100 to 150 nm, and/or a D (50%) ranging from 130 to 270 nm, preferably ranging from 140 to 260 nm, more preferably ranging from 150 to 250 nm, even more preferably ranging from 160 to 240 nm, most preferably ranging from 170 to 230 nm, and/or a D (90%) ranging from 200 to 500 nm, preferably ranging from 230 to 390 nm, more preferably ranging from 240 to 380 nm, even more preferably ranging from 250 to 370
  • the D (10%) and the D (50%) and the D (90%) are as given above, whereby all possible combinations of the values and ranges for D (10%), D (50%) and D (90%) are encompassed.
  • An especially preferred feed additive e.g. has a D v (10) ranging from 60 to 190 nm and a D v (50) ranging from 130 to 270 nm and a D v (90) ranging from 200 to 500 nm.
  • the most preferred feed additive has a D v (10) ranging from 90 to 160 nm and a D v (50) ranging from 170 to 230 nm and a D v (90) ranging from 270 to 350 nm.
  • Dispersions according to the present invention is also directed to the dispersion as obtained after having performed step iv) as well as to the following dispersion comprising:
  • hexose-dimers modified hexose- dimers, hexose-oligomers, modified hexose-oligomers, hexose-polymers, modified hexose-polymers, and any mixture thereof in an amount ranging from 5 to 30 weight-%, whereby further optionally at least one hexose may be present;
  • At least an antioxidant in an amount ranging from 0 to 20 weight-%; wherein the amount of ethoxyquin in said dispersion is ⁇ 0.5 weight-%; and wherein the amount of butylated hydroxytoluene in said dispersion is ⁇ 0.5 weight-%; all amounts based on the total weight of the dry matter of said dispersion.
  • the amount of water in the dispersion is chosen in such a way so that its final amount in the dispersion is preferably ranging from 30 to 60 weight-%, more preferably its final amount is ranging from 35 to 55 weight-%, most preferably its final amount is ranging from 40 to 50 weight-%, based on the total weight of the dispersion.
  • the amount of the carotenoid in the dispersion is chosen in such a way so that its final amount in the dispersion is preferably ranging from 1.0 to 20 weight-%, more preferably its final amount is ranging from 2.0 to 20 weight-%, most preferably its final amount is ranging from 9 to 16 weight-%, based on the total weight of the dry matter of the dispersion.
  • the amount of the lignin derivative is chosen in such a way so that its final amount in the dispersion is preferably ranging from 35 to 80 weight-%, more preferably its final amount is ranging from 40 to 75 weight-%, even more preferably its final amount is ranging from 42 to 68 weight-%, most preferably its final amount is ranging from 44 to 66 weight-%, based on the total weight of the dry matter of the dispersion.
  • the amount of the compound c) is chosen in such a way so that its final amount in the dispersion is preferably ranging from 10 to 30 weight-%, more preferably its final amount is ranging from 12 to 28 weight-%, based on the total weight of the dry matter of the dispersion.
  • the total amount of the antioxidant is chosen in such a way so that its final amount in the dispersion is preferably ranging from 1.0 to 12 weight-%, more preferably its final amount is ranging from 2.0 to 11 weight-%, most preferably its final amount is ranging from 5 to 11 weight-%, based on the total weight of the dry matter of the dispersion.
  • the particle sizes of the dispersion are the same as given above for the solid/dried feed additive.
  • the present invention is also directed to feed comprising the feed additive according to the present invention with the preferences as given above.
  • Feed or ‘feedingstuff') 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 aquatic animals in case of the carotenoid being astaxanthin or a derivative thereof.
  • Aquatic animals in the context of the present invention encompass crustaceae and fish, preferably farmed Crustacea such as shrimp and carnivorous species of farmed fish such as salmons, rainbow trout, brown trout (Salmo trutta) and gilthead seabream.
  • the feed is preferably for crustaceae and farmed fish, more preferably for salmonids, most preferably for salmons.
  • a typical composition for fish feed is e.g. shown in Table 14.
  • the feed additive may be added to the feed according to processes known to the person skilled in the art.
  • the feed additive according to the present invention may e.g. be added to the feed pre-extrusion with the other micro ingredients, preferably in an amount ranging from 0.01 to 0.1 weight-%, especially in an amount so that the amount of the carotenoid in the feed as given below is reached.
  • the feed additive according to the present invention may also be added to the feed post-extrusion.
  • the feed additive is added to the oil that is coated onto the feed pellets after they are extruded.
  • the feed comprises the supplemented carotenoid, especially astaxanthin or a derivative thereof, preferably in an amount ranging from 5 to 250 mg, more preferably in an amount ranging from 20 to 200 mg, based on 1 kg of feed.
  • the feed comprises the supplemented carotenoid, especially astaxanthin or a derivative thereof, preferably in an amount ranging from 5 to 150 mg, more preferably in an amount ranging from 20 to 100 mg, even more preferably in an amount ranging from 30 to 80 mg, most preferably in an amount ranging from 50 to 70 mg, based on 1 kg of feed.
  • the feed comprises the supplemented carotenoid, especially astaxanthin or a derivative thereof, preferably in an amount ranging from 50 to 250 mg, more preferably in an amount ranging from 100 to 230 mg, even more preferably in an amount ranging from 130 to 220 mg, most preferably in an amount ranging from 150 to 200 mg, based on 1 kg of feed, whereby the amount of the astaxanthin derivative is calculated in terms of astaxanthin.
  • feed additive according to the present invention or a feed comprising such feed additive is administered to an animal
  • the administration thereof results in a desired level of muscle retention in said animal.
  • the desired level of the carotenoid retained in the muscle leads to a pleasant, consumer-appealing flesh color similar to wild counterparts of said animal.
  • the feed additive according to the present invention comprising astaxanthin or any derivative thereof results especially in a muscle retention of at least 7% of astaxanthin in Atlantic salmon or at least 13% of astaxanthin in rainbow trout; i.e. 7% of the astaxanthin amount that has been ingested by Atlantic salmon and 13% of the astaxanthin amount that has been ingested by the rainbow trout, respectively, is retained in the muscle.
  • the feed additive according to the present invention comprising at least one carotenoid which can be used for the pigmentation of animals, especially aquatic animals, is stable per se and in feed as shown in Tables 7, 8, 10-12 and 15.
  • the present invention is further directed to the use of the feed additive or the feed according to the present invention for pigmentation of an animal excluding humans.
  • the animal to be pigmented is an aquatic animal.
  • Aquatic animals in the context of the present invention encompass crustaceae and fish, preferably farmed Crustacea such as shrimp and carnivorous species of farmed fish such as Atlantic and Pacific salmon (particularly Salmo salar and Oncorhynchus kisutch), rainbow trout ( Oncorhynchus mykiss), brown trout ( Salmo trutta ) and gilthead seabream ( Sporus aurata).
  • the feed additive or the feed according to the present invention is preferably used for pigmentation of crustaceae and farmed fish, more preferably for pigmentation of salmonids, most preferably for pigmentation of Atlantic salmon and rainbow trout.
  • the feed additive has to be eaten by the animal for a time period known to the person skilled in the art.
  • the aquatic animal needs to consume the feed additive for at least 3 months before slaughtering.
  • the aquatic animal In case the aquatic animal is salmon or salmon trout or rainbow trout, the aquatic animal needs to consume the feed additive for at least 3 months before slaughtering.
  • Another embodiment of the present invention is a method of pigmenting an animal excluding humans by administering a feed additive or a feed according to the present invention to said animal.
  • a feed additive or a feed according to the present invention to said animal.
  • said animal is an aquatic animal.
  • Aquatic animals in the context of the present invention encompass crustaceae and fish, preferably farmed Crustacea such as shrimp and carnivorous species of farmed fish such as Atlantic and Pacific salmon (particularly Salmo solar and Oncorhynchus kisutch), rainbow trout ( Oncorhynchus mykiss), brown trout (Salmo trutta ) and gilthead seabream ( Sparus aurata).
  • farmed Crustacea such as shrimp and carnivorous species of farmed fish such as Atlantic and Pacific salmon (particularly Salmo solar and Oncorhynchus kisutch), rainbow trout ( Oncorhynchus mykiss), brown trout (Salmo trutta ) and gilthead seabream ( Sparus aurata).
  • the present invention is preferably directed to a method of pigmenting crustaceae or farmed fish, more preferably to a method of pigmenting salmonids, most preferably to a method of pigmenting Atlantic and Pacific salmons.
  • the astaxanthin or the astaxanthin derivative is preferably used in an amount ranging from 5 to 150 mg, more preferably in an amount ranging from 20 to 100 mg, even more preferably in an amount ranging from 30 to 80 mg, most preferably in an amount ranging from 50 to 70 mg, based on 1 kg of feed, whereby the amount of the astaxanthin derivative is calculated in terms of astaxanthin.
  • the supplemented astaxanthin or astaxanthin derivative is preferably used in an amount ranging from 50 to 250 mg, more preferably in an amount ranging from 100 to 230 mg, even more preferably in an amount ranging from 130 to 220 mg, most preferably in an amount ranging from 150 to 200 mg, based on 1 kg of feed, whereby the amount of the astaxanthin derivative is calculated in terms of astaxanthin.
  • sucrose dried glucose syrups such as Glucidex 21 (as commercially available from Roquette) or Glucidex IT 47 (as commercially available from Roquette), dextrins such as Dextrin Yellow (as commercially available from Roquette) and modified food starch such as Capsul and Capsul HS (as commercially available from Ingredion) are used.
  • dried glucose syrups such as Glucidex 21 (as commercially available from Roquette) or Glucidex IT 47 (as commercially available from Roquette)
  • dextrins such as Dextrin Yellow (as commercially available from Roquette)
  • modified food starch such as Capsul and Capsul HS (as commercially available from Ingredion) are used.
  • the lignosulfonate, the compound c) and the water-soluble antioxidant are dissolved in deionized water 1) to obtain the so-called “matrix”.
  • the emulsion is sprayed into fluidized corn starch.
  • the obtained beadlets (solid feed additive according to the present invention) remains in the corn starch for 45 to 60 minutes.
  • the dried beadlets are sieved and the fraction with a particle size ranging from 160 to 630 pm used.
  • the dried beadlets are-dispersed in deionized water and measured using a particle analyzer DelsaTM Nano S (Beckmann Coulter, New Castle, DE, USA) via dynamic light scattering.
  • the measured particle sizes are given in Table 6.
  • sucrose dried glucose syrups such as Glucidex 21 (as commercially available from Roquette) or Glucidex IT 47 (as commercially available from Roquette), dextrins such as Dextrin Yellow (as commercially available from Roquette) and modified food starch such as Capsul and Capsul HS (as commercially available from Ingredion) are used.
  • dried glucose syrups such as Glucidex 21 (as commercially available from Roquette) or Glucidex IT 47 (as commercially available from Roquette)
  • dextrins such as Dextrin Yellow (as commercially available from Roquette)
  • modified food starch such as Capsul and Capsul HS (as commercially available from Ingredion) are used.
  • the lignosulfonate, the compound c) and the water-soluble antioxidant are dissolved in deionized water, including an adjustment to pH 7.2 using aqueous sodium hydroxide (20% weight /weight) (so-called “matrix”). An aliquot of 341 g is transferred to a reactor vessel and stirred for 20 minutes at 52°C and 1500 rpm using a rotor /stator device. Astaxanthin, the fat-soluble antioxidant (D/L- ⁇ -tocopherol) and an organic solvent is heated at the boiling point of said solvent until complete dissolution of astaxanthin and the fat-soluble antioxidant (so-called "active phase”).
  • the active phase is emulsified into the matrix for 30 min at 53°C and 10 000 rpm.
  • the pre-emulsion is homogenized at 150 bar.
  • the organic solvent is evaporated.
  • a liquid feed additive according to the present invention is obtained.
  • the emulsion (including optionally a viscosity adjustment via addition of water) is sprayed into fluidized corn starch.
  • the obtained beadlets (solid feed additive according to the present invention) remain in the corn starch for 45 to 60 minutes.
  • the dried beadlets are sieved (160-630 pm).
  • the dried beadlets are-dispersed in deionized water and measured using a particle analyzer DelsaTM Nano S (Beckmann Coulter, New Castle, DE, USA) via dynamic light scattering.
  • the measured particle sizes are given in Table 6.
  • Astaxanthin stability during stress testing exposing prototypes to ambient environment at 25°C / 60% r.h. and 40°C / 75% r.h.(feed additives according to examples 1-7) Aliquots of 120 mg are weighed into perforated capped plastic tubes. Thus, the samples are exposed to the environment during storage for 4 and 8 weeks in climatized rooms at 25°C / 60% relative humidity (r. h.) as well as 40°C / 75% r. h., respectively. The total astaxanthin concentration is determined by HPLC (high performance liquid chromatography) at the respective storage time. In brief, the aforementioned aliquot of 120 mg is transferred to a flask containing 200 mg BHT (butylated hydroxytyrosol).
  • BHT butylated hydroxytyrosol
  • BHT prevents further degradation of the astaxanthin during the analytical procedure.
  • the sample is re-dispersed in 10 mL deionized water at 50°C. After adding 100 mL ethanol and 80 ml dichloromethane, the mixture is kept for 30 min at room temperature. Afterwards, the sample is made up to 200 mL with dichloromethane and an aliquot of 10 mL is centrifuged for 5 min at 4000 rpm. The supernatant of the centrifuged stock solution is filled into amber glass vials for HPLC analysis. Astaxanthin retentions are calculated based on the initial concentration. Each test is performed two times. The average of the results is shown in Table 7. The accuracy is ⁇ 5%. The starting value is 100%. The results show that astaxanthin is physically stable under both conditions for at least 8 weeks.
  • Table 7 The accuracy is ⁇ 5%. The starting value is 100%.
  • Astaxanthin stability during per-se stability tests bv storing prototypes in sealed aluminum pouches at 25°C / 60% r. h. and 40°C / 75% r. h.(feed additives according to examples 1-7) Aliquots of 1.5 g are weighed into aluminum pouches and sealed. Samples are stored in climatized rooms at 25°C / 60% r. h as well as 40°C / 75% r. h. for 4 and 8 weeks. The total astaxanthin concentration is determined by HPLC at the respective storage time.
  • Table 8 The accuracy is ⁇ 5%. The starting value is 100%.
  • Example 8 has been carried out three times on large scale.
  • the composition is given in Table 6.
  • the particle size distribution of the obtained solid feed additives, measured via dynamic light scattering using especially the particle analyzer DelsaTM Nano S (Beckmann Coulter, New Castle, DE, USA), are as follows:
  • Table 9 Furthermore, the stability of these feed additives has been evaluated at 15°C, at 30°C and a relative humidity of 75%, as well as at 40°C and a relative humidity of 75%. The results as well as the filtration residues are shown in the following Tables 10-13: Table 10
  • Example 9 Fish trials using a feed additive according to example 6 a) Production of the feed
  • Pellets having a particle size of 7 and 9 mm are produced with the following composition:
  • the feed additive according to the present invention is added pre-extrusion with the other micro ingredients.
  • the 7 mm pellets are fed to fish with a weight ranging from 0.6-1.2 kg
  • the 9 mm pellets are fed to fish with a weight ranging from 1.2-3.0 kg.
  • the storage stability of the feed additive according to example 6 in the 9 mm pellets has also been determined.
  • the astaxanthin (“AXN”)content is measured 2 weeks, 4 weeks, 8 weeks and 12 weeks after storage at 23° C.
  • Usually fish feed is stored for a maximum of 4-6 weeks.
  • Table 15 the maximum loss is 10% after 12 weeks which fulfills the requirements of the market:
  • Table 15 b) Fish trial As fish salmon is used. 345 fish are randomly distributed into 3 cages (5 x 5 m steel cages) with 115 fish per cage. All fish are individually weighed and counted into the trial. The average body weight at the start of the trial is 805 g (minimum: 709 g; maximum: 880 g; coefficient of variation ("CV") 0.53%). Sampled fish are euthanized by a percussive blow to the head. The sampled fish is bled, gutted including the removal of the kidney, and weighed for dress-out-loss calculation. Photofish is used to assess content of fat and color in the Norwegian quality cut (so called "NQC”; see Fig. 1).
  • the trial started at October 17, 2019.
  • the fish was fed to satiation by two daily meals from start to 31st of October, and one daily meal from 1st of November to 28th of February, and two daily meals from 1st of March.
  • the daily ration was based on satiation feeding by hand, using distinctive meals.
  • the feeding rate is adjusted according to the feeding response of the fish in the cage.
  • the color evaluation of the NQC is done by Photofish (see Fig.2).
  • Photofish by AKVAGROUP https://www.akvagroup.com/software-/photofish) is based on automated photo analysis offish samples. Samples are cut from the NQC cutlet and placed on the test tray ready for photography, and the measurement board is passed through the Photofish box and photographed. The actual measurement process is automated and controlled by the software. The software calulates the color given as SaloFan score and the concentration of astaxanthin [mg/kg] and fat [%].
  • the CIE 1976 L*a*b* color space (also referred to as CIELAB) is one of the most popular color spaces for measuring object colors. It was defined by CIE in 1976 for color communication and is widely adopted today in many industries for color control and management.
  • L* indicates lightness and a* and b* are chromaticity coordinates
  • a* and b* are color directions: +a* is the red axis, -a' is the green axis, +b* is the yellow axis and -b* is the blue axis.
  • the L* and +a* and +b* were measured by a hand-held Minolta (type) on the positions indicated in Fig.3.
  • the muscle retention is calculated as follows:
  • the astaxanthin content in NQC as measured by photofish is 5.7 mg/kg (standard deviation: 0.2).
  • the lightness L* is 37.7 (standard deviation: 1.6), the redness a* is 10.3 (standard deviation: 0.9) and the yellowness is 13.2 (standard deviation: 1.3).
  • the muscle retention is 7.8% (standard deviation: 0.2).
  • Examples 10-12 Fish trials using a feed additive according to examples 2b. 4b and 6. respectively a) Production of the feed
  • Fillets are taken from the 10 fish closest to the average weight of each replicate tank. Fillet color is analyzed in 3 replicate locations within 1-2 hours of euthanasia using a Minolta chroma meter. Color readings are taken of the Norwegian Quality Cut (NQC) region approximately identified by each number in Fig.4. Readings are taken for mean redness, yellowness, lightness, hue, and chroma (see Table 17).
  • NQC Norwegian Quality Cut
  • NQC samples are taken from the 10 selected fillets.
  • the NQC includes a complete dorsal to ventral section, as shown in
  • Pigmentation efficacy is determined by 1) assessment of fillet color space measured by a chroma meter and, 2) measurement of muscle astaxanthin and astaxanthin retention.
  • astaxanthin sufficiently accumulats in the fillet to exceed the industry target minimum of 7 mg/kg fillet astaxanthin.
  • Table 17 Mean ⁇ standard deviation ("SD”) of fillet color characteristics, fillet astaxanthin and astaxanthin retention offish from day 0 to day 86.
  • rainbow trout fed with a feed comprising the feed additive according to the present invention shows the desired muscle retention.
  • Examples 13-14 Preparation of the feed additive according to the present invention The used ingredients and their amounts are given in Table 18. The preparation is as described for examples 1-7 above according to Method A b).
  • the dried beadlets are-dispersed in deionized water and measured using a particle analyzer DelsaTM Nano S (Beckmann Coulter, New Castle, DE, USA) via dynamic light scattering.
  • the measured particle sizes are given in Table 18.
  • Table 18 All amounts are given in weight-%, based on the total weight of the solid feed additive.
  • Examples 15-16 Fish trials using a feed additive according to examples 13 and 14. respectively a) Production of the feed
  • the fish trial is performed as described above for examples 10-12.
  • the average body weight at the start of the trial is 121.0 ⁇ 0.1 g. c) Results
  • Pigmentation efficacy is determined by 1) assessment of fillet color space measured by a chroma meter and, 2) measurement of muscle astaxanthin and astaxanthin retention. In all treatments, astaxanthin sufficiently accumulates in the fillet to exceed the industry target minimum of 7 mg/kg fillet astaxanthin.
  • Table 19 Mean ⁇ standard deviation ("SD”) of fillet color characteristics, fillet astaxanthin and astaxanthin retention offish from day 0 to day 86.
  • rainbow trout fed with a feed comprising the feed additive according to the present invention shows the desired muscle retention.

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Abstract

La présente invention concerne un additif alimentaire comprenant au moins un caroténoïde et un procédé pour sa fabrication. D'autres objets de la présente invention concernent des aliments pour animaux comprenant de tels additifs alimentaires, ainsi que des procédés de pigmentation et des utilisations correspondantes de tels additifs alimentaires et de tels aliments pour animaux.
PCT/EP2020/078565 2019-10-11 2020-10-12 Nouveaux additifs alimentaires de caroténoïdes WO2021069733A1 (fr)

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IT202200005453A1 (it) * 2022-03-21 2023-09-21 Green Innovation Gmbh Vitamins’vegetal booster / potenziatore vegetale di vitamine

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RU216224U1 (ru) * 2022-04-25 2023-01-24 Владимир Николаевич Малышев Шнек экструдера, обеспечивающий поэтапное снижение влажности в процессе экструдирования за счет влагоудаления в зоне экструдирования путем выпаривания

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