NZ232238A - Food products containing porous polymeric beads impregnated with a vitamin - Google Patents
Food products containing porous polymeric beads impregnated with a vitaminInfo
- Publication number
- NZ232238A NZ232238A NZ232238A NZ23223890A NZ232238A NZ 232238 A NZ232238 A NZ 232238A NZ 232238 A NZ232238 A NZ 232238A NZ 23223890 A NZ23223890 A NZ 23223890A NZ 232238 A NZ232238 A NZ 232238A
- Authority
- NZ
- New Zealand
- Prior art keywords
- beads
- food product
- vitamin
- food
- water
- Prior art date
Links
- 239000011324 bead Substances 0.000 title claims description 103
- 235000013305 food Nutrition 0.000 title claims description 69
- 229940088594 vitamin Drugs 0.000 title claims description 68
- 229930003231 vitamin Natural products 0.000 title claims description 68
- 235000013343 vitamin Nutrition 0.000 title claims description 68
- 239000011782 vitamin Substances 0.000 title claims description 68
- 150000003722 vitamin derivatives Chemical class 0.000 title claims description 32
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 42
- 239000000178 monomer Substances 0.000 claims description 40
- 238000000576 coating method Methods 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 23
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 18
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 17
- 239000011248 coating agent Substances 0.000 claims description 16
- 235000013339 cereals Nutrition 0.000 claims description 12
- 235000019155 vitamin A Nutrition 0.000 claims description 8
- 239000011719 vitamin A Substances 0.000 claims description 8
- 235000019154 vitamin C Nutrition 0.000 claims description 8
- 239000011718 vitamin C Substances 0.000 claims description 8
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 claims description 7
- 229930003268 Vitamin C Natural products 0.000 claims description 7
- 239000011159 matrix material Substances 0.000 claims description 7
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 claims description 5
- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 claims description 5
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 5
- 238000009472 formulation Methods 0.000 claims description 5
- 235000019168 vitamin K Nutrition 0.000 claims description 5
- 239000011712 vitamin K Substances 0.000 claims description 5
- 229940045997 vitamin a Drugs 0.000 claims description 5
- 238000010411 cooking Methods 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 235000019166 vitamin D Nutrition 0.000 claims description 4
- 239000011710 vitamin D Substances 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 2
- 229930003448 Vitamin K Natural products 0.000 claims description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 2
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 claims description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 2
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- 235000019156 vitamin B Nutrition 0.000 claims description 2
- 239000011720 vitamin B Substances 0.000 claims description 2
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- 229940046010 vitamin k Drugs 0.000 claims description 2
- 229930003316 Vitamin D Natural products 0.000 claims 1
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 claims 1
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- 238000000605 extraction Methods 0.000 description 9
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- 235000005473 carotenes Nutrition 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 229940040387 citrus pectin Drugs 0.000 description 1
- 239000009194 citrus pectin Substances 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical class CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000010944 ethyl methyl cellulose Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 235000021472 generally recognized as safe Nutrition 0.000 description 1
- 235000021552 granulated sugar Nutrition 0.000 description 1
- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 235000012171 hot beverage Nutrition 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 235000021539 instant coffee Nutrition 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920003087 methylethyl cellulose Polymers 0.000 description 1
- 235000020166 milkshake Nutrition 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 235000008935 nutritious Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940039748 oxalate Drugs 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 235000015108 pies Nutrition 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical group C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- PDEFQWNXOUGDJR-UHFFFAOYSA-M sodium;2,2-dichloropropanoate Chemical compound [Na+].CC(Cl)(Cl)C([O-])=O PDEFQWNXOUGDJR-UHFFFAOYSA-M 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 1
- 229920003176 water-insoluble polymer Polymers 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
- A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
- A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
-
- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
- A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
- A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
- A21D2/14—Organic oxygen compounds
-
- 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
- A23L7/00—Cereal-derived products; Malt products; Preparation or treatment thereof
- A23L7/10—Cereal-derived products
- A23L7/101—Addition of antibiotics, vitamins, amino-acids, or minerals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1635—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Food Science & Technology (AREA)
- Chemical & Material Sciences (AREA)
- Nutrition Science (AREA)
- Polymers & Plastics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Mycology (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- General Preparation And Processing Of Foods (AREA)
Description
New Zealand Paient Spedficaiion for Paient Number £32238
No.: Date:
232238
NO DRAWINGS
Priority Date(s):.... L.W,2.:.S-
Complete Specification riled:z±3a dass- (5k J \ 2-S1 Cj J /
Kblkll^.,
Publication Date: . P.O. Journal, No:
NEW ZEALAND
PATENTS ACT, ] 95.3
COMPLETE SPECIFICATION
■ENHANCED FOOD VITAMIN ADDITION BY MICROBEAD
DELIVERY"
I / We. WM WRIGLEY JR COMPANY, a corporation of the state of Delaware, USA, of 410 North Michigan Avenue, Chicago, Illinois 60611, CSA
hereby declare the invention for which I / we pray that a patent may granted to me /us, and the method by which it is to be performed, to be particularly described in and by the following statement:
(followed by page la)
r>
*
232 2
- 3«-
ENHANCED FOOD VITAMIN ADDITION BY MICROBEAD DELIVERY
BACKGROUND OF THE INVENTION
This invention relates to the addition of vitamins to food, and in particular, to the addition of vitamins to food by impregnating porous microbeads with vitamins and adding the microbeads to the food. Vitamins are essential in the diet of animals and humans. One problem in ensuring that foods have an adequate shelf life is the stability of vitamins added to foods to fortify them, i.e., make them more nutritious so that the consumer receives an adequate vitamin intake. Oxidation is one of the prime aspects of the problem. Some vitamins (e.g., carotene) are easily oxidized on contact with air. Other vitamins are more slowly oxidized but can still oxidize during the shelf-life of the product.
The stability of vitamins to oxidation is a particular problem in certain types of food. There is ^ considerable surface area for oxidation in many foods.
For instance, in breakfast cereals, particularly flakes, air readily circulates and permeates the food particularly during manufacturing and after the product is opened by the consumer. There is considerable surface area for oxidation in many foods.
SUMMARY OF THE INVENTION
According to the current invention, a food product is dispersed in water-insoluble, porous
232 2 3
polymeric beads that have microporous passages in them impregnated with one or more vitamins. In narrower aspects of this invention, the beads can be coated with water-soluble coatings to entrap the vitamins in the beads until the beads are exposed to water. Alternatively, the beads can be coated with coatings that melt when heated so that the vitamins are not released until the food is heated. In addition, the entrapment of fat-soluble vitamins (e.g., vitamins A, D, E, and K) is believed to be enhanced because the porous polymeric beads of the present invention exhibit an affinity toward water-insoluble compounds such as fat-soluble vitamin K.
DESCRIPTION OF THE PRESENTLY PREFERRED EMBODIMENTS OF THE INVENTION
In the present invention, a food product (or matrix) contains porous polymeric beads that have microporous passages impregnated with one or more vitamins. The vitamins include, but are not limited to, vitamins A, B, C, D, E and/or K. Also the term "vitamins" as used herein includes provitamins, and pharmaceutically acceptable salts of any of the aforesaid vitamins or provitamins. By "pharmaceuti-cally acceptable salts" is meant non-toxic acid addition salts and alkaline earth metal salts of such vitamins. The salts can be prepared in in situ during the final isolation and purification of the vitamins, or separately by reacting the free-base or acid functions of such vitamins with a suitable organic acid or base. Representative acid addition salts include hydrochloride, hydrobromide, sulphate, bisulphate, acetate, oxalate, valerate, oleate, palmitate,
stearate, laurate, borate, benzoate, lactate,
phosphate, tosylate, mesylate, citrate, maleate, fumarate, succinate, tartrate, glucoheptonate, lauryl sulfate salts and the like. Representative alkali or
232238
alkaline earth metal salts include sodium/ calcium, potassium, and magnesium salts and the like.
By "food product" or "food matrix" is meant an edible substance that delivers nutrition or taste pleasure to humans or other animals. Food matrices include but are not limited to meats, baked goods (i.e. breads, cakes, cookies, and pies and the like), puddings, syrups, gums, and the like. Food matrices also include dry or condensed mixes that upon addition of water or other ingredients form an edible siabstance that can be eaten immediately or eaten after cooking or further processing. Mixes include baked good mixes, soup mixes, pudding mixes, and the like.
Food matrices also include liquid beverages and concentrates for liquid beverages. With liquid beverages or concentrates, the porous polymeric beads containing vitamins can be added to the liquid immediately before the product is packaged so the vitamin will not be lost. The vitamin is released to the drink from the beads during storage and shipment of the product. This release can be delayed by using a water-soluble coating that dissolves over time.
Food matrices also include powdered or granular mixes for liquid beverages that are mixed with water to produce liquid beverages. A powdered or granular beverage mix usually includes a beverage base that ordinarily has flavoring (e.g. coffee or citrus flavor) and often a sweetener and the like. Beverage bases are known in the art and include instant coffee, milk shakes, fruit drinks, and the like. The vitamin-impregnated microbeads of this invention can be coated with a water-soluble coating that dissolves to release vitamin upon addition of water to the mix. Alternatively, the beads can be coated with a coating (e.g.
232 2 3
fat) that melts when hot water is added, a feature desirable in hot drink mixes such as cocoa or coffee.
The present invention contemplates the addition to the food matrix described above of water-insoluble porous polymeric beads preferably of a size not discernible to the consumer where the beads have porous passages impregnated with one or more vitamins described above. The preferred size range is between 10 and 100 microns, and the most preferred is between 20 and 50 microns. Preferably, the porous polymeric beads are coated with a coating that influences the release of the vitamins within the microporous passages in the porous polymeric beads.
Such coatings include zein, wax, gum arabic, fatty acids, fats, food grade shellac, carbohydrates, silica, water-insoluble polymers (e.g., polyvinyl acetate), proteins such as casein, starches, dextrins, or modified or unmodified cellulosics such as ethyl, methyl, hydroxypropyl, or hydroxyethyl cellulose. The use of such coated beads controls the release of vitamins in the porous polymeric beads typically such that the vitamins within the beads are released at a time when the food product is used by the consumer.
The polymeric beads of this invention are polymerized in a fashion that the microporous passages are formed during polymerization. Such a procedure is described below. Residual monomers are then extracted as described below so that the beads can be impregnated with vitamins. The beads are "then optionally coated with one or more coatings and added to the food matrix. The details of the microparticle polymerization,
monomer extraction, and microparticle impregnation and coating are described below followed by Examples I through V that illustrate various specific foods and polymeric beads of the present invention.
232 2
I. POLYMERIC BEAD POLYMERIZATION
In one embodiment of the present invention, the polymeric beads can be polymerized as taught in U.S. Patent 4,690,825 to Won dated September 1, 1987, the entire disclosure of which is incorporated herein by reference. Specifically, the beads used in the food matrix of the present invention can be prepared by polymerizing one or more polymers by a free radical suspension polymerization process. A monomer or pair of comonomers is dissolved in an inert porogen to form a solution that is suspended in a phase or solvent incompatible with that solution. Such a phase or solvent can be water with stabilizing additives. After the solution is suspended in the phase, the solution and phase are agitated to form droplets of solution suspended in the phase. After the formation of the droplets, the monomer or monomers in the droplets are activated to initiate a polymerization reaction in which the monomer is cross-linked or where two or more monomers are polymerized to form porous beads having a network of pores with the porogen within the network of pores. The activation may be triggered by an initiator that is insoluble with the monomer solution. Alternatively, activation may be triggered by an energy source such as radiation. The inert porogen serves as an internal diluent during polymerization and introduces the desired sponge-like microporous structure or network of pores into the finished bead. The inert porogen does not react with the monomer present during polymerization or inhibit the polymerization. The beads may or may not swell in the inert porogen. After formulation of the porous beads, the beads are separated from the phase and subjected to one or more extraction steps such as washing to remove any unreacted monomer or impurity from the beads. After extraction, described below, the beads may be dried to obtain a powder-like
232 2
substance that includes the beads but without either porogen or solvent.
An example of a polymer that can be used to form porous polymeric beads for the food product of this invention is a copolymer of divinylbenzene and styrene. Such beads can be polymerized in water as taught in the aforesaid Won patent or as described in Example I below. If such a copolymer is used, the monomers (which are not food approved additions) are typically not completely reacted, and excess monomer concentration should be reduced to levels less than 30ppm [as illustrated by the styrene monomer standards for food-grade styrene-butadiene rubber (Food Chemical Codex, 3rd Edition, pg. 42.)] if the beads are to be used in a food product. Typically, the amount of free cross linking agent (divinylbenzene) in the beads after polymerization is quite low compared with styrene because divinylbenzene has two reaction sites, and thus is more reactive than styrene. Thus, the extraction is primarily to extract styrene monomer, the divinylbenzene monomer present in the polymer already being close to or lower than the 30ppm value. An extraction procedure is explained in Section II below and in Example I.
To avoid or reduce the effort required in monomer extraction, one can copolymerize divinylbenzene with a food-grade monomer that can polymerize with divinylbenzene. By a food-grade monomer is meant any monomer that is a food additive permitted for direct addition to food for human consumption under 21 CFR, part 172 or substances generally recognized as safe under 21 CFR, part 182. Examples of such monomers are one or more of the following: estragole, limonene, carvone, eugenol and ocimene. Limonene is illustrative inasmuch as it is a naturally-occurring compound in
232
many citrus fruits. Still other examples are provided in Example IV, infra.
The food-grade monomer need not be extracted unless one wants to extract it for flavor reasons. But in many instances, the food-grade monomer may enhance the flavor of the food. Thus, any extraction of monomer after polymerization may only have to focus on divinylbenzene reduction, a comparatively simple proposition because it is already in comparatively low concentration.
II. MONOMER EXTRACTION
If monomer extraction is desired or required, it can be accomplished by washing the beads first with water followed by several (preferably three) washings of isopropanol, four to five washings with acetone and four to five washings with hexane. The excess solvent is removed by evaporation under a nitrogen blanket to leave dry beads having a powder-like consistency.
III. POLYMERIC BEAD IMPREGNATION WITH VITAMINS
The impregnation of pores in the polymeric beads with vitamins can be accomplished by soaking the beads in equal or greater weight of a solution containing the vitamin(s) of interest so that the beads are completed immersed in the solution. The impregnation proceeds over a period of at least six and preferably forty-eight hours. The impregnation may be carried out at a reduced temperature if the stability or volatility of the particular vitamin is of a particular concern. Of the total dry weight of the loaded beads after impregnation, 60% or even more may be vitamin. Such loadings are possibly using this procedure, although some bead/vitamin combinations will yield lower loadings.
When impregnating the microbeads with a water-soluble vitamin (e.g., B complex or vitamin C),
23
the vitamin should be dissolved in an aqueous solution to which the microbeads are added. When impregnating the beads with a fat-soluble vitamin (e.g., vitamins A, D or K), the vitamin should be dissolved in an oil or fat to which the microbeads are added. The fat or oil can be heated slighted if the stability of the vitamin permits so that the fat or oil can be absorbed readily into the microbeads. Alternatively, the fat or oil can be dissolved in an organic solvent so that the resulting solution is less viscous and can be absorbed more readily into the beads.
IV. POLYMERIC BEAD COATING
As indicated above, the porous polymeric beads are preferably coated with a coating that retards the release of the vitamins from the pores of the beads or prevents the premature release of the vitamins during storage. Illustrative coatings include water-so liable or permeable compositions such as hydroxypropyl methyl cellulose, sugars and the like. Depending on the thickness and porosity of the water-soluble or permeable coatings, such coatings retard the release of the vitamins in the pores of the polymeric beads by first requiring the coating to dissolve before the vitamin is released.
Water-insoluble coatings may also be employed. Such coatings include food grade shellac as disclosed in U.S. Patent No. 4,673,577 to Patel dated June 16, 1987 that is incorporated herein by reference. Water insoluble wax coatings also include waxes such as those disclosed in U.S. Patent Application Serial No. 07/137,114 entitled Method of Making Chewing Gum with Wax-Coated Delayed Release Ingredients by Steven E. Zibell that is incorporated herein by reference, and zein.
232 2
Fatty acids can also be employed as coatings for the beads. Fatty acids, depending on chain length, have varying water solubilities. A mixture of fatty acids can be prepared that has the desired degree of water solubility that controls the dissolution of the coating until the desired time. Combinations or mixtures of water-soluble and water-insoluble coating agents may be employed as coatings for the porous beads to control or release of the vitamins from the beads.
A variety of methods to coat the beads can be used. Several are described generally below, and in detail in the examples infra.
A. Spray Drying
An emulsion/solution of vitamin-impregnated beads and encapsulant is atomized into an air stream that evaporates the solvent to leave coated beads. A Niro spray dryer may be used. This technique should be used where the particular vitamin is exposed to air only for a brief period, if at all. It is believed to be a workable technique in some cases because when vitamins entrapped in the passages in the beads, they cannot be exposed to air very readily.
B. Spray Chilling
A suspension of beads in molten encapsulant is atomized and chilled to produce beads coated with encapsulant. This technique can be used for vitamins such as niacin which are quite stable to heat. However, it should be used cautiously where the temperature of the melted encapsulant is higher than a temperature where a particular vitamin may degrade. Such temperatures are known to one of ordinary skill in the art, so the selection of an appropriate encapsulant is believed to be within the ability of one of ordinary skill in the art.
232 2
C. Fluid Bed Coating
Beads are suspended in an air stream (fluidized bed). The beads are sprayed with a solution of the encapsulant in a volatile solvent. The solvent is evaporated or dried by the air stream to produce beads coated by the encapsulant. The technique can be used where no short-term oxidation problems are experienced with a particular vitamin.
D. Granulati on/Agglomeration
A damp mix of beads and granulant is prepared,
then dried and ground to desired particle size. This is a preferred node of coating beads for encapsulating vitamins except those that may be moisture sensitive when exposed to air (e.g., ascorbic acid). In such cases, it may be desired to prepare the mix in an oxygen-free environment (e.g., under a nitrogen blanket).
E. Gel Encapsulation
Beads are suspended in a gelatin solution that is cooled to gel, then ground to desired particle size.
F. Melt Blending
Beads are mixed into a molten agglomerant which is cooled to harden and ground to the desired particle size. Again, the choice of agglomerant should be made to have a melting temperature below the temperature where the particular vitamin may be unstable.
V. ADDITION OF BEADS TO THE FOOD PRODUCT
The vitamin-impregnated microbeads of this invention can be added to a food matrix in a variety of ways. The food can be wet, and the beads added by mixing them into the food mechanically. The food can then be dried, preferably at a temperature lower than a temperature where vitamin stability is compromised.
n
232 2 3
Exposing the product to reduced pressures during drying helps to keep the temperatures sufficiently low. A good example of such formulation techniques is a breakfast cereal. The vitamin-impregnated beads are mixed in the cereal while the cereal is wet, and the cereal is dried under reduced pressure at a temperature less than 100°C to form a dried cereal. The dried cereal may be of the type to be cooked later, or consumed without cooking.
Other methods of adding vitamin-impregnated microbeads to foods include dry blending the microbeads in a dry food mix (e.g. a bread or cookie mix) before hydration and baking; or formulating the beads into a slurry that that is sprayed onto the food.
The following examples of the invention are provided by way of explanation and illustration. They are not intended to limit the invention.
Example I Thiamine - Fortified Cookie Dough A) Preparation of Microbeads
Gelatin (250 mg) is added to a three-necked flask purged with nitrogen. Water (150 ml) is heated to 50°C and added to the flask to dissolve the gelatin. While the contents of the flask are stirred, a freshly prepared solution of benzoyl peroxide (1.25 grams; 1.03 mmole) and styrene (22.9 grams; 0.22 mole) monomer is added, followed by divinylbenzene (12.0 grams; 42 mmoles). The mixture is heated to 90°C while maintaining a constant stirring rate, and passing nitrogen through the flask.
The mixture is stirred for two hours, and cooled to room temperature, and the supernatant liquid is decanted. The polymer beads are washed with hexane several times, and stirred in hexane (200 ml) for two hours to remove any excess divinylbenzene or styrene,
rs
2322
and dried overnight at 50°C in a vacuum to yield dry microbeads.
B) Impregnation of Beads with Thiamine Chloride Hydrochloride
The beads prepared in part A are soaked in an equal weight of a 50% aqueous solution of thiamine chloride hydrochloride for 48 hours. The beads are filtered from solution. The beads are cooled to -20°C in a vacuum to remove the water.
O
O
C) Thiamine - Fortified Cookie Dough
The beads of part B are mixed with the ingredients in Table I to produce a dry cookie dough.
Table I
Ingredient Amount (grams)
Flour 100.0
Salt 0.93
Shortening 28.4
Sucrose 57.8
Sodium Bicarbonate 1.1
Dextrose 0.9
Microbeads 0.14
The cookie dough of Table I is mixed with a sufficient amount of water so that the dough is thick and tacky to the touch. The cookies are baked at 350°F unti1 brown.
Example II Bread Dough Fortified With Vitamin A A) Vitamin A - Impregnated Beads
The microbeads prepared in Example I part A are immersed in an equal weight of a solution containing one part vitamin A and nine parts vegetable oil. The microbead mixture is stored for 48 hours at
232
room temperature in a dark room. The excess solution is filtered from the beads.
B) Vitamin A. - Fortified Bread Dough
The microbeads of part A are added to the ingredients in Table II to produce a dry bread dough.
Table II
Ingredient Amount f grams)
Flour 40.0
Yeast 2.0
Sucrose 0.5
Beads 0.016
The dry bread dough is made into a bread by adding a sufficient amount of warm water to the dry mix above to make a pliable, tack-free dough. The dough is allowed to rise, kneaded, and allowed to rise a second time. It is then placed in a bread pan, and baked at 350°F until golden brown.
Example III
Vitamin - Fortified Breakfast Cereal Flakes
A) Microbeads Impregnated With Thiamine,
Riboflavin and Niacin
Microbeads prepared as described in Example I part A are immersed in a aqueous solution containing equal amounts of thiamine, riboflavin, and niacin. The excess solution is removed by filtration.
B) Vitamin - Fortified Breakfast Flakes
The beads of part A are formulated into a slurry of water (24%), sucrose (75%) and beads (1% by weight). The sugar slurry is sprayed onto conventional breakfast cereal flakes (e.g. corn or bran flakes). The water is evaporated during spraying to produce
2322 38
breakfast flakes fortified with thiamine, riboflavin and niacin.
Example IV Alternative Microbead Formulations Various microbead polymers are possible consistent with the teachings of this invention. A number of types of microbeads can be prepared following the procedure set forth in Example I part A, altering the amount of monomer to be polymerized with divinylbenzene, or changing the monomer to be polymerized with divinylbenzene. Alternatively, the amount of divinylbenzene can be varied. A summary of such microbead formulations is set forth in Table III below.
Table III
Monomer Amount
Divi nylbenz ene Amount
a)
Estragole
32.6
g;
0.22 mole
33
g
b)
Estragole
32.6
g;
0.22 mole
98
g o
c)
Allyl cyclo-hexyl propionate
43.12
g;
0.22 mole
12
g
d)
Allyl cyclo-hexyl propionate
43.12
g;
0.22 mole
33
g o
e)
Allyl cyclo-hexyl propionate
43.12
g;
0.22 mole
97
g
f)
Ocimene
29.92
g;
0.22 mole
12
g
g)
Ocimene
29.92
g;
0.22 mole
33
g
h)
Ocimene
29.92
g;
0.22 mole
97
g
i)
Divinyl-sulfide
18.96
g;
0.22 mole
12-
■97
2322 38
Divinylbenzene Monomer Monomer Amount Amount
N j) Vinyl
! methylketone 15.42 g; 0.22 mole 12-97 g k) 4-methyl-5-vinyl thiazole 27.5 g; 0.22 mole 12-97 g
1) 2-methyl-5-vinyl pyrazine 26.1 g; 0.22 mole 12-97 g m) Vinyl pyrazine 23.32 g; 0.22 mole 12-97 g n) l-penten-3-ol 18.92 g; 0.22 mole 12-97 g o) l-octen-3-ol 28.16 g; 0.22 mole 12-97 g p) carvone 33.00 g; 0.22 mole 12-97 g q) limonene 29.92 g; 0.22 mole 12-97 g r) diallyl-
disulfide 32.18 g; 0.22 mole 12-97 g s) allylsulfide 25.13 g; 0.22 mole 12-97 g t) allyl alpha ionone 51.12 g; 0.22 mole 12-97 g
The monomers identified above to be polymer-O ized with divinylbenzene can also be combined with styrene to yield the desired beads. In addition, divinylbenzene can be replaced with allylacrylate as the crosslinker or with other suitable divinyl compounds .
Microbeads produced from the polymers described above are made from food-grade monomers that can polymerize with divinylbenzene. The residual food-grade monomer in the microbeads can contribute flavor to the food. Accordingly, to achieve a proper blend of food-grade monomer with the flavoring of the food to achieve good taste, certain combinations of food-grade monomer and food flavorings are preferred, as indicated in Table VI below.
2322 38
,-^N
o o
Food Flavoring Mint
Onion
Citrus
Peanut
Meat
Fruit
Cinnamon
Table VI
Monomer(s)
Estragole, ocimene, vinyl-methyl ketone, l-octen-3-ol,
1-penten-3-ol, carvone, limonene, allyl alpha ionone
Divinylsulfide,
diallyldisulfide, allylsulfide Ocimene, carvone, limonene
4-methyl-5-vinylthiazole,
2-methyl-5-vinylpyrazine, vinylpyrazine
4-methyl-5-vinylthiazole, 2-methyl-5-vinylpyrazine, vinylpyrazine,
diallyldisulfide, allylsulfide
Eugenol, allylcyclohexyl propinate, limonene
Estragole, eugenol, limonene
The polymerized food-grade monomer also forms a polymer with regions that have an affinity toward certain vitamins that can be absorbed into the micro-beads. This can improve the impregnation of the vitamins into the pores of the polymeric beads. These regions are essentially polymeric chains of food-grade monomer. If the vitamin can dissolve into or has an affinity toward the food-grade monomer, the vitamin will likely have an affinity toward the polymeric chains in these regions.
Example V Vitamin C Fortified Candy A. Preparation of Microbeads Impregnated
With Vitamin C
Microbeads from Example I part A are immersed in an aqueous solution of 20% ascorbic acid (vitamin C).
o o
232 2 38
The beads are soaked for 24 hours in the absence of light. The beads are filtered from the excess solution and are immediately coated by spray chilling with wax.
B. Preparation of Vitamin C Fortified Fruit
Slice Candy
The ingredients in Table VI are combined in the manner described below to produce the captioned candy.
Table VI JELLY FRUIT SLICES, LEMON
Sugar
22
lb
Corn Syrup
16
lb
Water
12
qt
Slow-Setting Citrus Pectin
8
oz
Sodium Citrate (dissolved in water)
2
oz
Citric Acid (dissolved in water)
4
oz
Yellow Color
2
tsp
Oil of Lemon
4
tsp
Vitamin C Microbeads
2
lb
The water is placed in a large copper pan and heated to the boiling point. The pectin is mixed dry with seven pounds of sugar and added to the boiling water, while stirring constantly. When boiling again, the dissolved sodium citrate and one third of the dissolved citric acid are added, while stirring in one third of the dissolved citric acid are added, while stirring in the balance of the sugar and the corn syrup gradually. The batch is cooked to 108°F and is then removed. The microbeads are then added. Two small portions, about five pounds each are taken from the batch and poured into small pans; the largest portion
2322 3
Q
O
o
is kept in the cooking pan. The first small portion is colored yellow, flavored with one teaspoonful of oil of lemon and one teaspoonful of citric acid. This is mixed through well, poured out rapidly on a paper-lined slab, and spread out rapidly to about 1/16 inch thickness.
The second small portion is flavored with one teaspoonful of oil of lemon. One teaspoonful of citric acid is also stirred in. This is then poured on top of the first layer, and spread rapidly and evenly to produce a "peel" layer.
The remaining large portion is colored yellow and flavored with 2 teaspoonfuls of oil of lemon. Four teaspoonfuls of citric acid are stirred into the large batch. The batch is then run out through the funnel rapidly into jelly bar molds and allowed to set. The jellies are then removed, and placed on boards lined with wax paper.
The lemon-peel batch on the slab is turned upside down on the slab and sprinkled with some starch. The paper on top is dampened and removed, and sugar is sprinkled on top. After the lemon-peel batch is turned over again, the lemon jelly bars are wrapped around with the peel, leaving the bottom as it is. The wrapped rolls are rolled in fine granulated sugar and allowed to set until the "peels" adhere to the bars. The jelly is then sliced into fine thin slices and rolled in sugar. After drying, the slices are placed in crystal pans and crystallized in a conventional manner.
Example VI
Polymeric Beads Including Stvrene-Butadiene Rubber Styrene-butadiene rubber (10.0 g) is dissolved in toluene (90.0 g). In a separate beaker, polyvinylalcohol (1.5 g) is dissolved in water (450.0 g) at about 40°C. The copolymer solution is
Claims (21)
1. A food product, comprising a food matrix, containing water-insoluble porous polymeric beads impregnated with a vitamin.
2. The food product of claim 1 wherein said porous polymeric beads are coated with a water-soluble coating.
3. The food product of claim 1 wherein said porous polymeric beads are coated with a water-insoluble coating.
4. The food product of claim 1 wherein said vitamin is fat-soluble.
5. The food product of claim 4 wherein said vitamin is selected from the group consisting of vitamin A, vitamin D or vitamin K, or combinations thereof.
6. The food product of claim 1 wherein said vitamin is water-soluble.
7. The food product of claim 6 wherein said vitamin is selected from the group consisting of vitamin B complex or vitamin C, or combinations thereof.
8. The food product of claim 1 wherein said porous polymeric beads are polymerized from styrene and divinylbenzene. - 20 - - 21 - 232 2 38
9. The food product of claim 1 wherein said porous polymeric beads are polymerized from divinylbenzene and a food-grade monomer that can polymerize with divinylbenzene.
10. A method of making a food product, comprising impregnating water-soluble porous polymeric beads with a vitamin; and adding said beads to a food product.
11. The method of claim 10 wherein said food product is a cereal, and said beads are coated on said cereal.
12. The method of claim 10 wherein said food product is a cooked cereal, and said beads are added before cooking.
13. The method of claim 10 wherein said food product is a cereal, and said method further comprises providing said cereal in a wet state, adding said beads to said cereal in said wet state, and drying said cereal.
14. The method of claim 13 wherein said wet cereal is at a temperature below 100°C when said beads are added.
15. The method of claim 10 wherein said beads are coated with a water-soluble coating prior to addition to said food product.
16. The method of claim 10 wherein said beads are coated with a water-soluble coating prior to addition to said food product. - 21 - - 22 - 232238
17. The method of claim 16 wherein said food product is provided in a wet state prior to bead addition, and is dried after bead addition.
18. The method of claim 17 wherein said food product is dried by exposing it to a reduced pressure at a temperature less than 100°C.
19. A food product substantially as herein described with reference to the foregoing examples.
20. A method of making a food product substantially as herein described with reference to the foregoing examples.
21. A food product when made by the method of any one of claims 10 to 18 and 20. f.'tf ithir/ic-'J jf . -v-itOn if - / ' Bp hit/tH«lr authorised Agim. A. J. PARK. A SON. - 22 -
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US31170289A | 1989-02-16 | 1989-02-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
NZ232238A true NZ232238A (en) | 1991-07-26 |
Family
ID=23208079
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NZ232238A NZ232238A (en) | 1989-02-16 | 1990-01-24 | Food products containing porous polymeric beads impregnated with a vitamin |
Country Status (4)
Country | Link |
---|---|
CN (1) | CN1044892A (en) |
AU (1) | AU5099390A (en) |
NZ (1) | NZ232238A (en) |
WO (1) | WO1990009108A1 (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5270063A (en) * | 1992-08-03 | 1993-12-14 | Kellogg Company | Ready-to-eat cereal products enriched with beta-carotene |
DE10047515A1 (en) * | 2000-09-22 | 2002-04-18 | Stolle Gmbh & Co Kg Geb | Vitaminized meat products for healthier eating are obtained by tumbling the meat with a vegetable oil-coated vitamin mixture |
DE10301354A1 (en) | 2003-01-16 | 2004-07-29 | Esa Patentverwertungsagentur Sachsen-Anhalt Gmbh | To produce raw sausages, with an accelerated ripening, folic acid and/or folates are added with the herbs/spices for an even distribution to provide micrococcus and/or lactobacillus |
US20050003070A1 (en) * | 2003-07-03 | 2005-01-06 | Foster David V. | Shelf stable vitamin C in oatmeal products |
DE102009055018A1 (en) | 2009-12-18 | 2011-06-22 | Hochschule Anhalt (FH); Hochschule für angewandte Wissenschaften, 06366 | Raw sausage with accelerated ripening process and process for its preparation |
EP3416494A4 (en) * | 2016-02-17 | 2019-11-13 | Corr-Jensen Inc. | Time release vitamins and minerals in edible oils |
CN115902071A (en) * | 2023-02-23 | 2023-04-04 | 北京华大吉比爱生物技术有限公司 | Method for detecting fat-soluble vitamins in sample |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3767824A (en) * | 1971-05-17 | 1973-10-23 | Quaker Oats Co | Method of vitamin coating cereal products |
US3782963A (en) * | 1971-05-17 | 1974-01-01 | Quaker Oats Co | Method of vitamin coating cereal products |
US3767825A (en) * | 1971-06-18 | 1973-10-23 | Merck & Co Inc | Method of coating food particles with a blend of vitamins a and c |
US4038422A (en) * | 1975-01-23 | 1977-07-26 | The Quaker Oats Company | Coated baked goods |
JPS5231981A (en) * | 1975-08-18 | 1977-03-10 | Takeda Chem Ind Ltd | Microcapsule preparation method |
US4230687A (en) * | 1978-05-30 | 1980-10-28 | Griffith Laboratories U.S.A., Inc. | Encapsulation of active agents as microdispersions in homogeneous natural polymeric matrices |
JPS61174940A (en) * | 1985-01-29 | 1986-08-06 | Oogawara Kakoki Kk | Single core microcapsule coated with wax and its preparation |
US4690825A (en) * | 1985-10-04 | 1987-09-01 | Advanced Polymer Systems, Inc. | Method for delivering an active ingredient by controlled time release utilizing a novel delivery vehicle which can be prepared by a process utilizing the active ingredient as a porogen |
-
1990
- 1990-01-24 NZ NZ232238A patent/NZ232238A/en unknown
- 1990-01-25 WO PCT/US1990/000569 patent/WO1990009108A1/en unknown
- 1990-01-25 AU AU50993/90A patent/AU5099390A/en not_active Abandoned
- 1990-02-16 CN CN90100730A patent/CN1044892A/en active Pending
Also Published As
Publication number | Publication date |
---|---|
CN1044892A (en) | 1990-08-29 |
WO1990009108A1 (en) | 1990-08-23 |
AU5099390A (en) | 1990-09-05 |
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