IL29174A - Fungicidal polyphosphates - Google Patents
Fungicidal polyphosphatesInfo
- Publication number
- IL29174A IL29174A IL29174A IL2917467A IL29174A IL 29174 A IL29174 A IL 29174A IL 29174 A IL29174 A IL 29174A IL 2917467 A IL2917467 A IL 2917467A IL 29174 A IL29174 A IL 29174A
- Authority
- IL
- Israel
- Prior art keywords
- juice
- growth
- sodium
- food material
- polyphosphates
- Prior art date
Links
- 229920000388 Polyphosphate Polymers 0.000 title claims description 42
- 239000001205 polyphosphate Substances 0.000 title claims description 42
- 235000011176 polyphosphates Nutrition 0.000 title claims description 42
- 230000000855 fungicidal effect Effects 0.000 title claims description 7
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 44
- 235000013305 food Nutrition 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 26
- 239000000463 material Substances 0.000 claims description 23
- 235000011389 fruit/vegetable juice Nutrition 0.000 claims description 15
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 12
- 239000011734 sodium Substances 0.000 claims description 12
- 229910052708 sodium Inorganic materials 0.000 claims description 12
- 235000015197 apple juice Nutrition 0.000 claims description 10
- 241000233866 Fungi Species 0.000 claims description 9
- 229910052700 potassium Inorganic materials 0.000 claims description 9
- 239000011591 potassium Substances 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 150000001340 alkali metals Chemical class 0.000 claims description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 235000019674 grape juice Nutrition 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 4
- 235000019987 cider Nutrition 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 235000015205 orange juice Nutrition 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 235000013399 edible fruits Nutrition 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
- 235000013405 beer Nutrition 0.000 claims description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 2
- 239000005452 food preservative Substances 0.000 claims description 2
- 235000012471 refrigerated dough Nutrition 0.000 claims description 2
- 235000014101 wine Nutrition 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 3
- 235000015203 fruit juice Nutrition 0.000 claims 2
- NYQDCVLCJXRDSK-UHFFFAOYSA-N Bromofos Chemical compound COP(=S)(OC)OC1=CC(Cl)=C(Br)C=C1Cl NYQDCVLCJXRDSK-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000012530 fluid Substances 0.000 claims 1
- 235000019249 food preservative Nutrition 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 238000012856 packing Methods 0.000 claims 1
- 239000011885 synergistic combination Substances 0.000 claims 1
- 235000015192 vegetable juice Nutrition 0.000 claims 1
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 41
- 235000019830 sodium polyphosphate Nutrition 0.000 description 31
- 239000002609 medium Substances 0.000 description 21
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 20
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 20
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 19
- 239000000126 substance Substances 0.000 description 17
- 239000000654 additive Substances 0.000 description 16
- 241000228245 Aspergillus niger Species 0.000 description 13
- 230000000996 additive effect Effects 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 235000019832 sodium triphosphate Nutrition 0.000 description 11
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 10
- 229910019142 PO4 Inorganic materials 0.000 description 9
- 238000002474 experimental method Methods 0.000 description 9
- 235000021317 phosphate Nutrition 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 9
- 238000011534 incubation Methods 0.000 description 8
- 244000005700 microbiome Species 0.000 description 8
- 238000000855 fermentation Methods 0.000 description 7
- 230000004151 fermentation Effects 0.000 description 7
- 230000001408 fungistatic effect Effects 0.000 description 7
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 7
- 229940099402 potassium metaphosphate Drugs 0.000 description 7
- OQZCJRJRGMMSGK-UHFFFAOYSA-M potassium metaphosphate Chemical compound [K+].[O-]P(=O)=O OQZCJRJRGMMSGK-UHFFFAOYSA-M 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 244000061456 Solanum tuberosum Species 0.000 description 6
- 235000002595 Solanum tuberosum Nutrition 0.000 description 6
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 235000019820 disodium diphosphate Nutrition 0.000 description 6
- GYQBBRRVRKFJRG-UHFFFAOYSA-L disodium pyrophosphate Chemical compound [Na+].[Na+].OP([O-])(=O)OP(O)([O-])=O GYQBBRRVRKFJRG-UHFFFAOYSA-L 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 239000003755 preservative agent Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 238000011081 inoculation Methods 0.000 description 5
- 235000012015 potatoes Nutrition 0.000 description 5
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 5
- 235000010234 sodium benzoate Nutrition 0.000 description 5
- 239000004299 sodium benzoate Substances 0.000 description 5
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 5
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 4
- 241000228143 Penicillium Species 0.000 description 4
- 241000122123 Penicillium italicum Species 0.000 description 4
- 241000219094 Vitaceae Species 0.000 description 4
- 239000008121 dextrose Substances 0.000 description 4
- 235000021021 grapes Nutrition 0.000 description 4
- 238000010348 incorporation Methods 0.000 description 4
- 235000013997 pineapple juice Nutrition 0.000 description 4
- 235000010241 potassium sorbate Nutrition 0.000 description 4
- 239000004302 potassium sorbate Substances 0.000 description 4
- 229940069338 potassium sorbate Drugs 0.000 description 4
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 4
- 235000010334 sodium propionate Nutrition 0.000 description 4
- 239000004324 sodium propionate Substances 0.000 description 4
- 229960003212 sodium propionate Drugs 0.000 description 4
- 210000005253 yeast cell Anatomy 0.000 description 4
- 241000636501 Asparagus aspergillus Species 0.000 description 3
- 241000228197 Aspergillus flavus Species 0.000 description 3
- 241000220225 Malus Species 0.000 description 3
- -1 ammonium Chemical group 0.000 description 3
- 229940041514 candida albicans extract Drugs 0.000 description 3
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 230000002906 microbiologic effect Effects 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- 239000012138 yeast extract Substances 0.000 description 3
- 239000001888 Peptone Substances 0.000 description 2
- 108010080698 Peptones Proteins 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- 235000021016 apples Nutrition 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 235000011180 diphosphates Nutrition 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 235000021472 generally recognized as safe Nutrition 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000002054 inoculum Substances 0.000 description 2
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 235000019319 peptone Nutrition 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 description 1
- MOMKYJPSVWEWPM-UHFFFAOYSA-N 4-(chloromethyl)-2-(4-methylphenyl)-1,3-thiazole Chemical compound C1=CC(C)=CC=C1C1=NC(CCl)=CS1 MOMKYJPSVWEWPM-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 229930195730 Aflatoxin Natural products 0.000 description 1
- XWIYFDMXXLINPU-UHFFFAOYSA-N Aflatoxin G Chemical compound O=C1OCCC2=C1C(=O)OC1=C2C(OC)=CC2=C1C1C=COC1O2 XWIYFDMXXLINPU-UHFFFAOYSA-N 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 244000105627 Cajanus indicus Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 241001535823 Cloeosiphon aspergillus Species 0.000 description 1
- 244000017020 Ipomoea batatas Species 0.000 description 1
- 235000002678 Ipomoea batatas Nutrition 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 241000220324 Pyrus Species 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 239000005409 aflatoxin Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 235000013332 fish product Nutrition 0.000 description 1
- 239000012737 fresh medium Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 238000013383 initial experiment Methods 0.000 description 1
- 229910052816 inorganic phosphate Inorganic materials 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 235000013622 meat product Nutrition 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 235000019828 potassium polyphosphate Nutrition 0.000 description 1
- 239000001965 potato dextrose agar Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 229940048084 pyrophosphate Drugs 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
- 235000019983 sodium metaphosphate Nutrition 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- 229940075554 sorbate Drugs 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- RYCLIXPGLDDLTM-UHFFFAOYSA-J tetrapotassium;phosphonato phosphate Chemical compound [K+].[K+].[K+].[K+].[O-]P([O-])(=O)OP([O-])([O-])=O RYCLIXPGLDDLTM-UHFFFAOYSA-J 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
- A23B2/00—Preservation of foods or foodstuffs, in general
- A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
- A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
- A23B2/788—Inorganic compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
- A01N59/26—Phosphorus; Compounds thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Inorganic Chemistry (AREA)
- Agronomy & Crop Science (AREA)
- Health & Medical Sciences (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Non-Alcoholic Beverages (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Storage Of Fruits Or Vegetables (AREA)
Description
1'EJniUM I Π D TilHJ1 ! Ί1 DR. REINHOLD COHN |Π 3 1 Ί I Π 1 ■ ' Ί ' 11 DR. MICHAEL COHN I Π 3 "J N D ' D ΊΊ ISRAEL SHACHTER B Sc. .DJ 1 B . UI "J N 101 ' PATENTS AND DESIGNS ORDINANCE SPECIFICATION Fungicidal polyphosphates STATJPFER CHEMICAL COMPANY* a corporation organized under the laws of the State of Delaware, of 299 Park Avenue, Ν.Τ·. 10017, U.S.A. do hereby declare the nature of this invention and in what manner the same is to be performed, to be particularly described and ascertained in and by the following statement :- 29174/2 - la - The present invention relates to the use of certain polyphosphates as fungicidal agents, and more particularly, it relates to retarding and eliminating spoilage in a wide variety of perishable food materials which are susceptible to fungus attack, still more particularly, it relates to the application of certai polyphosphates to perishable food materials in orde to preserve such materials against deterioration due -to the action of fungi including molds as well as yeasts.
The application of polyphosphates, including tetrasodium pyrophosphate, sodium tripolyphosphate, and sodium hexametaphos- phate is known in the art of preserving certain meat and fish products. While the application of such phosphate materials in meat and fish has provided satisfactory solutions to the problems including color and fat retention, serious problems of spoilage of these and other food materials of vegetable as well as animal origin are still known to exist. Therefore, it is the principal a I x ; object of the present invention to overcome and eliminate the V shortcomings inherent in the prior art and to provide a method for preserving food materials against spoilage caused, in particular, by the action of fungi. ■·'■,' In accordance with the present invention, we have no discovered that nutrient containing materials, e.g.,, food materials of vegetable as well as animal origin can be preserved against the action of deleterious fungi, including molds as well as yeast, in an unexpectedly, highly effective manner by the incorporation therein of a small but effective amount of a .. substance comprising a polymeric phosphate of the type; wherein X represents hydrogen or an alkali metal including ammonium, which is preferably sodium or p¾assium; and Y represents an alkali metal including ammonium, which is preferably sodium or potassium; ' represents an average chain length not less than about 14 and no more than about 100. Λ preferred range comprises polyphosphates having H between about 14 and about 37* 5 e term "average ave chain length" as employed herein, is intended to represent a statistical average chain length or indication of the number of recurrin units linked together comprising the anionic species . Such an average is determined by titration as described in Van Wazer et al. Anal. Chem. 26, 1755-9 (195^)· The term "fungic dal" employed herein is intended to include both retardation of growth, i.e., fungistatic action, as well as killing of the organisms involved.
In the practice of the present invention it was found, quite unexpectedly, that while the orthophosphates showed no signs of fungicidal or fungistatic activity and, in fact, enhanced growth in certain cases, all polyphosphates which were tested from average chain length of 2 to about 1700 exhibited fungicidal activity. The pyrophosphates, sodium acid pyrophosphate (SAPP) and tetrasodium pyrophosphate (TSPP) and tripolyphos phates of sodium and potassium exerted only a relatively weak inhibitory effect upon fungi (yeast and molds) . The high polymer potassium polyphosphates (Nave = 1000+) were also found fungicidally active. Considering levels of activity versus solubility problems in the high polymers, however, the sodium polyphosphates having average chain lengths from about lk to about 37 are preferred.
Polyphosphates can be incorporated into the food or other material susceptible of fungus attack and spoilage by any suitable method or means known in the art, including but not limited to incorporation by surface treatment operations such as dipping, flooding, well as incorporation by direct admixture either to form a solution or blend with food to be consumed. When the high molecular weight polyphosphate anions are incorporated by direct admixture, the preferable range of concentration of the polyphosphate in the food, on a weight basi is between about 0.570 and about 2.0$. In situations where a surface treatment of foods is employed, the preferable concentration of the polyphosphate in the liquid dip, flood, or spray solution is preferably within the range between about 5 an about 20$ on a weight basis. Since these polyphosphates are generally recognized as safe (GRAS), however, any effective amou can be employed.
The method of the present invention finds specific application in areas including the following, which are considered to be representative only: potatoes (including Irish as well as sweet potatoes), fruits, e.g., apples, pears, grapes, and citrus fruits, vegetables, e.g., onions, tomatoes, malt, grain prior to milling, and cheese. The method of application o phosphates preferred for the above listed food products comprise surface treatment, e.g., flooding or dipping. Other representative specific applications include applications in animal feeds (to control aflatoxin producing molds), pet foods, in juices to control molds, beers, wines, and in refrigerated doughs. The preferred method of incorporation of phosphates into the latter group of food materials is by way of admixing the polyphosphates in the product to be consumed.
The polyphosphates of the present invention have been found to exhibit synergistic action in combination with other food preservative agents including benzoates, sorbates, propionates, etc. Thus, the use of the polyphosphates of the present invention in combination with other chemical agents is within the scope of the present invention.
Having thus described the invention in general terms reference is now made to specific examples which are not to be construed as unduly limiting thereof.
EXAMPLE 1 Process apple juice was used in this example as a medium to study fungistatic effects of polyphosphates. A series of flasks were filled with such apple juice.
The following polyphosphates were added to the juice to give concentrations of 1$ by weight. 1. sodium hexametaphosphate 2. sodium polyphosphate (35) 3. potassium metaphosphate (Ca. 1000) h. potassium polymetaphosphate (Ca. 1700) One group of flasks were kept at room temperature (25°C.) expose to the atmosphere, without covering the flasks, so that natural contamination could occur and lead to spoilage of the juice. Spoilage was observed in the controls which had no chemical additive .
Another group of flasks was inoculated with a suspensi of yeast cells and was incubated at 30°C.
After 1 week, both groups of flasks containing polyphosphates showed a well preserved apple juice, whereas in the respective controls yeast fermentation started after about 12 hours. The controls without purposely added inoculum, but which had been exposed to the atmosphere also showed growth of molds.
From samples of apple juice to which 1$ of polyphosphates had been added, and which were inoculated with yeast, fractions were pipetted out and transferred into fresh apple juice, which contained no preservative. No yeast grew in the fresh media, and thus the polyphosphates appear to have fungicidal effects.
EXAMPLE 2 In another experiment employing apple juice as the medium of microbiological spoilage, the effects of different inorganic phosphates were tested against a variety of fungi: a. Aspergillus niger b. Penicillium italicum c. Wild yeast isolated from spoiled juice d. baker's yeast, Saccharomyces cerevisiae e. a blue-green mold, isolated from spoiled apples.
The following phosphates were added to portions of appl juice to a final concentration of 1. Disodium orthophosphate 2. Sodium acid pyrophosphate 3. Tetrasodium pyrophosphate h. Sodium tripolyphosphate . Sodium hexametaphosphate (av. 9) 6. Sodium polyphosphate (av. 18) 7. Sodium polyphosphate (av. 20) 8. Sodium polyphosphate (av. 31) 9. Sodium polyphosphate (av. 35) Inoculation of portions of the juice containing said phosphates was carried out by use of suspensions of spores from the molds, o suspensions of cells of yeasts, respectively. Incubation temperature was 25°C. which condition assured good growth facilities as was seen in the controls which contained no phosphates, and in which heavy growth could be observed from 1-2 days after inoculation.
No inhibition was observed in the samples of juice to which had been added orthophosphate. It was further observed that tetrasodium pyrophosphate and tripolyphosphate acted as slight inhibitors for fungal growth. Especially good inhibition was achieved by the use of sodium hexametaphosphate (av. 9) and of sodium polyphosphate (18-35). The latter group acted as chemical preservatives in foods, and preserved the juices to which spores of molds or yeast cells had been added for up to 6 weeks.
EXAMPLE 3 In this experiment, a liquid medium containing 1.5$ malt extract and 3$ dextrose was applied to study the effects of different phosphates upon molds.
The following molds were tested: a. Aspergillus niger b. Penicillium italicum c. a green mold isolated from rotten potatoes d. a yellow mold isolated from rotten potatoes A series of phosphates was tested whereby these chemicals were added to the nutrient growth medium in amounts yielding a final concentration of 1$. 1. Disodium orthophosphate 2. Sodium acid pyrophosphate 3. Tetrasodium pyrophosphate h . Sodium tripolyphosphate . Sodium hexametaphosphate (av. 9) 6. Sodium polyphosphate (av. 18) 7- Sodium polyphosphate (av. 20) 8. Sodium polyphosphate (av. 31) 9. Sodium polyphosphate (av. 35) Inoculation was carried out with suspensions of spores of the above mentioned molds. Temperature of incubation was 30° The flasks which contained disodium orthophosphate or no -preserving chemical, which were used as controls, started to sho visible signs of growth of molds overnigh .
Sodium acid pyrophosphate gave no significant inhibitory effect whereas tetrasodium pyrophosphate and sodium tripoly-phosphate were useful inhibitors especially for the two molds isolated from potatoes, which respective samples did not show growth of mold for up to h weeks. Surprisingly, better inhibition was found in the longer chain polyphosphates. All sodium polyphosphates (9-35) as tested in this experiment prevented the growth of Aspergillus niger, Penicillium italicum, and of two molds isolated from rotten potatoes.
EXAMPLE k The high polymerized potassium metaphosphates with average chain lengths between 1000 and 2000 were included in this experiment to determine fungistatic properties of these chemicals in comparison with sodium polyphosphates and with previously known preservatives.
Since the solubility of the high polymerized potassium metaphosphates is very low in aqueous media, they were solubilize by sodium salts. In particular sodium hexametaphosphate can be used to solubilize potassium metaphosphate, thus giving a system of a combined action of two fungistatic acting chemicals. The test medium in which the preserving chemicals were tested contained 1.5$ malt extract and 370 dextrose and was enriched with 0.5$ yeast extract to supply growth factors and vitamins, togethe with trace minerals. s ·· - The chemicals to be tested were added to portions of this broth in amounts to give a concentration of 0.5$ and in a few cases of 0.25$. Inoculation was carried out with suspension of spores of the mold Aspergillus niger and with cells of baker' yeast, Saccharomyces cerevisiae, respectively. A series of flasks containing no preserving chemicals was prepared and used as control for the growth studies.
All flasks were incubated at 50° C.
The tested chemicals in the experiment were: 1. sodium hexametaphosphate 2. potassium metaphosphate Ca. 1000 chain length, dissolve in sodium hexametaphosphate 3. potassium sorbate . sodium benzoate · sodium propionate After k days of incubation, yeast grew in the controls and in the flasks containing sodium benzoate or sodium propionat After 5 days of incubation turbidity readings were carried out with the flasks which had been inoculated with yeast. For every single experimental condition (a certain chemical additive) ten parallel flasks had been prepared, so that the turbidity readings could be averaged. Based on the turbidity given by the control assigned a value of 100$ growth, the following growth figures were obtained: $ Growth of Yeast with 0.5$ potassium sorbate with 0.5$ sodium benzoate with 0.5$ sodium propionate with 0-5$ sodium hexametaphosphate with 0.5$ sodium polyphosphate (av. chain length 35) with 0.5$ potassium metaphosphate plus 0.25$ sodium hexametaphosphate with 0.25$ potassium metaphosphate plus 0.12$ sodium hexametaphosphate The part of flasks which had been inoculated with spor of Aspergillus niger was evaluated after 10 days of incubation. Heavy growth of mold was then observed in the controls and also in the samples with potassium sorbate, sodium benzoate, or sodium propionate. Samples with sodium hexametaphosphate, sodiu polyphosphate (35) or potassium metaphosphate, prevented the growth of A. niger under the same conditions.
EXAMPLE 5 Inhibition of the growth of the mold Aspergillus niger was studied with malt extract as the growth medium. Inhibitory effects of different polyphosphates were compared with the effec of the salts of known fungistatic preservatives.
Thus, to portions of malt extract the following chemicals were added in such an amount that they yielded a concentration of 1%. 1. Sodium pyrophosphate, as a 50:50 mixture of sodium acid pyrophosphate and tetrasodium pyrophosphate 2. Sodium tripolyphosphate, pH adjusted with H3PO4 to 6.0. 3. Sodium hexametaphosphate h . Long chain sodium polyphosphate . Potassium sorbate 6. Sodium benzoate 7- Sodium propionate The flasks containing the malt extract and the given chemicals were then inoculated with a suspension of spores of the mold Aspergillus niger. a A series of flasks was also prepared which contained n preserving chemicals but also was inoculated with A. niger and served as controls.
All the flasks were then incubated at 30°C. for k days After this time the controls showed heavy mold growth. A thick for nd h v b k orulation appeared in the controls. The known preservatives propionate, benzoate, and sorbate showed also some growth of mycelium of the mold A. niger, although the amount of mycelium formed was less than in the controls, proving some inhibition.
A slight inhibition shown by the decreased amount of mycelium, as compared to the controls, was also exerted by pyrophosphate or tripolyphosphate. In the samples containing either sodium hexametaphosphate or a long chain polyphosphate, however, growth was completely inhibited. The malt extract in these cases was completely clear. None of spores of A. niger which ha been introduced by a heavy inoculation had sporulated and grown.
EXAMPLE 6 The effects of different polyphosphates upon the growt of two molds, Aspergillus niger and a Penicillium species, as als against yeast, Saccharomyces cerevisiae were tested.
The mold Aspergillus niger had been grown on potato dextrose agar. Therefrom spores were washed off with sterile water yielding a dark colored suspension.
Another mold, from the species Penicillium had been isolated from a moldy lemon. In a similar way to that described above, a suspension of spores was prepared which was used as inoculum in the test.
The third microorganism used in this experiment was baker's yeast, Saccharomyces cerevisiae.
The test medium for microbiological growth contained 1.5$ malt extract, 3-0$ corn sugar, 0.3$ yeast extract, and 0.2$ peptone. Portions of this medium were filled into flasks.
Different polyphosphates were then added to a concentration of The flasks were inoculated with portions of 1 ml of: a. a suspension of spores of Aspergillus niger b. a suspension of spores of a Penicillium species c. a suspension of cells of yeasts Incubation was carried out at 30°C. for 2 weeks.
After 2 weeks Aspergillus niger had formed heavy mycelia and was sporulating in all controls without polyphosphates as well as in the samples containing tetrasodium or tetrapotassium pyrophosphate. In flasks containing potassium tripolyphosphate, sodium hexametaphosphate, or sodium polyphosphates 15, 18, 20, 31, 35, growth of mold was completely inhibited.
Also after 2 weeks incubation, the growth of the Penicillium species was inhibited by potassium tripolyphosphate, sodium hexametaphosphate, or sodium polyphosphates 15, 18, 20, 31, 35- Similar results were obtained with yeast which had heavily grown in the controls. Polyphosphates with chain length 3, 11, 15, 18, 20, 31, 35 prevented the growth of yeast.
EXAMPLE 7 Unpasteurized apple cider was filled into a series of flasks. Different polyphosphates were added to some of them. Another group of flasks was kept without additives. All flasks were stored at room temperature (25°C.) without any further precautions to spoilage.
I /V¾Lt L Results after 6 weeks storage: Concentration Color Microbiological Additive of additive of spoilage in cider Cider Sodium tripoly or i$> dark brown moldy phosphate Sodium polypho 0.5 or 1°, golden unspoiled phate (15) Sodium polypho phate (18) 0.5 or 1°, golden unspoiled Sodium polypho phate (20) 0.5 or i¾ golden unspoiled Sodium polypho phate (31) 0.5 or i0/ golden unspoiled Sodium polypho phate (35) 0.5 or 1°, golden unspoiled no additive (in 5 flasks) dark brown moldy on surface and yeast growt on bottom of flasks Note: The number given in parenthesis with sodium polyphosphates refers to the analytically established average chain lengt EXAMPLE 8 Fresh grapes were ground up and pressed through cloth to obtain grape juice. No attempt was made to work under sterile conditions or to get rid of the naturally occurring yeasts on the grapes. On the contrary, it was observed that some grapes had been starting to rot at the stem end. So it was assured that natural spoilage microorganisms were in the juice.
Portions of this grape juice were filled into flasks to which different polyphosphates were added. All flasks were store without any further precautions towards spoilage, at 25°C.
After 7 days of storage samples with 2. sodium polyphosphate, chain lengths 15 to 35 , were well preserved and did not show any signs of fermentation by yeast or of growth of molds.
Samples to which were added sodium chloride, or tap water, or which contained no additive, and the samples which served as controls spoiled after 2 days of storage by yeast fermentation and also by growth of molds.
EXAMPLE 9 Processed pineapple juice was taken out of the cans, filled into a series of flasks and kept exposed to natural contamination by mold spores and yeasts present in the atmosphere especially of a laboratory in which moldy fruits had been previously handled.
To portions of this pineapple juice different polyphosphates were added giving concentrations of 1$ or 2.5$ in the juice .
A series of flasks without additives served as controls After 7 days storage at room temperature (25°C.) the juices which contained 1 of sodium polyphosphates (18-35) or of 2.50 of sodium polyphosphates (9-35) were well preserved without any signs of spoilage by yeasts or molds.
The controls stored under the same conditions (7 days °C.) showed yeast fermentation or heavy growth of molds.
EXAMPLE 10 Orange juice was pressed out of over-ripe already mushy oranges.
Portions of this juice were filled into a series of flasks, and different polyphosphates were added to these flasks in quantities to give 1$ or 2$ in the juice.
After 7 days of storage at 25 °C all the controls whic contained no polyphosphates were spoiled by yeast fermentation, and mold growth, whereas l# or of sodium hexametaphosphate or sodium polyphosphate 15, 18, 20, 31 or 35 had preserved the orange juice.
EXAMPLE 11 The growth of different molds was studied on a liquid malt medium. This medium contained 1.5$ malt extract, 3·0 corn sugar, 0.3$ yeast extract, and 0.2$ peptone. Portions of this medium were filled into flasks to which different polyphosphates were added to a final concentration of 2.5$ in the liquid broth.
All the flasks were then inoculated with suspension of spores of the following molds; a. Aspergillus flavus b. Penicillium italicum c. Aspergillus niger d. a yellow mold isolated from oranges The additives were: Potassium tripolyphosphate Sodium hexametaphosphate (ll) Sodium polyphosphate (18) Sodium polyphosphate (20) Sodium polyphosphate (31) Sodium polyphosphate (35) A series of flasks with sodium chloride as an additive and one series without additives served as controls.
The flasks were incubated at 30°C. After 3 days heavy mold growth was observed in all controls having been inoculated with the four different molds. The mold Aspergillus flavus grew The sodium polyphosphates, with chain lengths 11 throu 35, completely preserved the malt medium which comprised an idea medium for the growth of molds for 3 weeks.
A similar test as described with molds was performed with yeast, Saccharomyces cerevisiae.
Yeast was added at a concentration to give 50,000 cell per ml in the malt medium.
Whereas the control showed heavy fermentation and yeas growth after 3 days, in the flasks with sodium polyphosphate, yeast did not grow and the medium stayed clear and unchanged for the whole time of the experiment up to 3 weeks.
EXAMPLE 12 Sodium polyphosphates gave synergistic effects of fungistatic activity when used together with propionate or benzoate.
A series of flasks was prepared containing 1.5$ malt extract and 3$ dextrose in solution. Sodium polyphosphates and the two above mentioned preservatives were added to these flasks alone and in combinations.
Then all flasks were inoculated with portions of a suspension of yeast cells. The calculated concentration of yeas cells in the broth was 3 x 105· cells/ml.
Incubation was then carried out at 30°C. for 20 hours. After this time turbidity readings were taken. The turbidity obtained in the controls which had no chemical additive, was taken as 100$, clear broth gave 0$.
Growth of yeast in percent 1$ Sodium hexametaphosphate 13$ 1$ Sodium polyphosphate (av. chain length 35) 10$ 0.1$ Na- propionate 80$ 0.5$ Na- propionate 58$ 1$ Na- propionate 39$ ζ"0.05$ Na- propionate + ? 0.5$ Sodium hexametaphosphate^ 5$ 0.05$ Na- propionate + ? (. *5 Sodium metaphosphate^) 3$ £0.25$ Na- propionate + 0.05$ Sodium metaphosphatej $ 0.05$ methyl-p-hydroxy benzoate 70$ Co.025$ methyl-p-hydroxy benzoate + } .0-5 Sodium metaphosphate -J 2$ EXAMPLE 13 The data presented by way of the following table illustrate an increase in fungicidal activity observed in regard to polyphosphates of increasing chain lengths against Saccharomyces cerevisiae.
TfVfcU- 11 Saccharomyces Cerevisiae Yeast in apple juice, after 12 days: Initial concentration 60, 000 6 j 000 βοο 60 Additive yeast yeast yeast yeast cells cells cells cells per ml per ml. per ml. per ml. 1$ Vitrafos (12) *** #* * * 1$ Na-metaph. 16 ** #* * 0 1$ - 11 - 18 #* * ♦ 0 1$ ■Ά - 11 - J) 0 0 1$ - 11 - 37 *· 0 0 0 1$ K-polymeta-phos 0 0 0 0 in Vitrafos — P NaCl *#* *·*# *** No additive ##* *·** #** 0 No fermentation 29174/2' Based on experience derived from conducting initial experiments 1 through 19, the additional, more' quantitative experiments hereinafter set forth were carried out. These additional experiments are considered to present a more highly reliable indication of the true effects of the medium chain length polyphosphates under service conditions.
EXAMPLE 14 - This example is presented in tabular form below. It illustrates extended retardation of spoilage by medium chain length polyphosphates. · Test Medium: Malt Extract Microorganisms Tested: Aspergillus flavus, initial concentra- 29174/2 EXAMPLE .15 TABLE IV-Test Medium: Malt Extract Microorganisms Tested: Yeast, initial concn. 6 x 103 per ml EXAMPLE 16 TABLE V Medium: Malt Extract (1.5 ) & Dextrose {> ) Microorganisms Tested: Aspergillus flavus, Penicill. italic, Asp. niger, Yeast Concn . Stor . Results after days Addi ve of Add. Temp 1 Asper . Pencill. Asper.
°C. flavus italic . niger Yeas very very sPaOio 2.5 25 heavy slight slight heavy growth growth growth growth (NaP03)Nave 12 2.5 25 growth trace trace heavy growth growth. growth (NaP03)Nave 2.5 25 growth trace trace no growth growth growth (NaP03)Nave 16 2.5 25 growth trace trace no growth growth growth (NaP03)Nave 18 2.5 25 slight no trace no growth growth growth growth (NaP03)Nave 33 2.5 25 trace trace no no growth growth growth growth (NaP03)Nave 37 2.5 ! 25 no trace no no growth growth growth growth Control 0 25 very very very very heavy heavy heavy heavy growth growth growth growth EXAMPLE .17 TABLE VI Test Medium: Apple Juice Microorganisms Tested: Yeast, Mold (Samples kept open exposed to air, not inoculated) EXAMPLE 18 TABLE VII Test Medium: Orange Juice pH 4.10 Microorganisms Tested: Natural Yeast, not inoculated Concn. Stor .
Additive of Add. Temp. Results °C. 2 days 14 days 30 days Na5P30lo 2 5 preserved spoiled spoiled 1 5 spoiled spoiled spoiled ( NaP03)Nave 12 2 25 preserved spoiled spoiled 1 25 spoiled spoiled spoiled (NaP03)Nave U. 2 25 preserved spoiled spoiled 1 25 preserved spoiled spoiled (NaP03)Nave 18 2 25 preserved preserved preserved 1 25 preserved preserved preserved (NaP03)Nave 33 2 25 preserved preserved preserved 1 25 preserved preserved preserved Control 0 25 spoiled spoiled spoiled EXAMPLE 19 TABLE VIII Test Medium: Pineapple Juice and Grape Juice Microorganisms Tested: Natural yeasts & molds Concn. Stor. Results after 7 days Additive of Add. Temp . Pineapple Juice, Grape Juice, °G. exposed to air pressed in laboratory Na2HP04 1 25 moldy spoiled Na2H2P207 1 25 moldy spoiled Na4P207 .5 25 moldy spoiled K4P207 • 5 25 preserved spoiled Na5P30 io 1 25 moldy spoiled K5P3O10 2 .5 25 moldy spoiled Na6P401 3 1 25 moldy spoiled (NaP03)Nave 12 1 25 moldy spoiled 2 .5 25 preserved spoiled (NaP03)NaVe l2* 1 25 preserved spoiled 2 .5 25 preserved spoiled (NaP03)Nave 16 1 5 preserved spoiled 2 .5 5 preserved preserved (NaP03)Nave 18 1 25 preserved spoiled 2 .5 25 preserved spoiled (NaP03)Nave 33 1 25 preserved spoiled 2 .5 25 preserved preserved (NaP03)Nave 37 1 25 preserved spoiled 2 .5 25 preserved preserved Control 0 25 moldy spoiled Having thus described the invention with reference to specific examples thereof, many modifications and alterations wil become apparent to those skilled in the art without departing from the spirit or scope thereof. 29174/2 • 25 -
Claims (26)
1. The fungicidal method which comprises a l ing to the habitat of the fungU3 an effective amount of a polyphosphate of the type: wherein X ia selected from the group consisting of hydrogen and alkali metal; Y represents alkali metal; and iave represents an average chain length of between about 14 and about 100.
2. The method of Claim 1 in which H is between ave about 14 and 37.
3. 3· The method of Claim 1 in which X is hydrogen.
4. 4· The method of Claim 1 in which X is an alkali metal.
5. The met od of Claim 4 in which said alkali met-il is nodium.
6. The method of Claim 4 in which said alkali raotr,l is potassium.
7. The method of Claim 4 in which said alkali metal is ammonium.
8. The method of Claim 1 in which Y is sodium.
9. The method of Claim 1 in which Y is potassium. 29X74/2 , ίϊ - 27 -
10. 10· The method of preserving food materials from spoilage caused by the growth of fungus including mold or yeast which comprises incorporating in aueh a food material a polyphosphate of the type: wherein X is selected from the group consisting of hydrogen and alkali metal; Y represents alkal metal j and N repre- ave sents an average chain length of between about 14 and about 100·
11. 11· The method according to Claim 10 in which said food material is an edible fluid and Have is between about 16 and about 37.
12. 12· A method according to Claim 11» wherein said food material is fruit jutoe ·
13. 13· A method according to Claim 12, wherein said Juice is apple juice.
14. 14· A method according to Claim 12, wherein said fruit juice is grape juice.
15. 15· method according to Claim 12, wherein said frui juice is orange juice.
16. A method according to Claim 10» wherein said food materi al is animal feed.
17. A method according to Claim 11, wherein said food material is beer. 29174/2 , 28 -
18. A method according to C.V>im 11, wherein said food material is wine.
19. 19· A method according to Claim 10, wherein said food material Is refrigerated dough.
20. A method according to Claim 10 or 11, wherein said polyphosphate is used in a synergistic combination with another food preservative selected from the group consisting of benzoates, sorbites and propionates.
21. 21· A method according to Claim 10, wherein said food material is of the type preserved by packing in ice and said polyphosphates are incorporated in said ice.
22. A composition of matter inhibited against spoilage caused by the growth of fungi and having improved taste appeal which comprises a food material having incorporated therein between about 0.1 and about 5 percent by weight of a polyphosphate of the type: wherein X is selected from the group consisting of hydrogen and alkali netal; Y represents alkali metal; and N repre- ave sents an average chain length of between about 14 and about 100.
23. The composition of Claim 22, in which said food material comprises an edible liquid.
24. The composition of Claim 23 in which 3aid food - 29 material compriseB a fruit or vegetable juice.
25. The composition of Claim 23 in which said food material comprises apple juice.
26. The composition of Claim 23 in which said food material comprises apple cider.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60659867A | 1967-01-03 | 1967-01-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL29174A true IL29174A (en) | 1971-07-28 |
Family
ID=24428630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL29174A IL29174A (en) | 1967-01-03 | 1967-12-20 | Fungicidal polyphosphates |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT293849B (en) |
| BE (1) | BE708864A (en) |
| CH (1) | CH487597A (en) |
| DE (1) | DE1792760C3 (en) |
| FR (1) | FR1568003A (en) |
| GB (1) | GB1199460A (en) |
| IL (1) | IL29174A (en) |
| NL (1) | NL150664B (en) |
| NO (1) | NO124292B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6261619B1 (en) | 1994-02-24 | 2001-07-17 | The Procter & Gamble Co. | Noncarbonated beverage products with improved microbial stability and processes for preparing |
| US6294214B1 (en) | 1994-02-24 | 2001-09-25 | The Procter & Gamble Co. | Noncarbonated beverage products with improved microbial stability and processes for preparing |
| WO1996026648A1 (en) | 1995-02-28 | 1996-09-06 | The Procter & Gamble Company | Preparation of noncarbonated beverage products having superior microbial stability |
| DE19633895C1 (en) * | 1996-08-22 | 1997-11-20 | Benckiser Knapsack Ladenburg | Use of acidic sodium polyphosphates for germ inhibition of mold and yeasts |
-
1967
- 1967-12-20 IL IL29174A patent/IL29174A/en unknown
- 1967-12-28 GB GB58759/67A patent/GB1199460A/en not_active Expired
- 1967-12-28 CH CH1826367A patent/CH487597A/en not_active IP Right Cessation
- 1967-12-28 DE DE1792760A patent/DE1792760C3/en not_active Expired
-
1968
- 1968-01-02 AT AT1768A patent/AT293849B/en not_active IP Right Cessation
- 1968-01-02 FR FR1568003D patent/FR1568003A/fr not_active Expired
- 1968-01-02 NO NO6815A patent/NO124292B/no unknown
- 1968-01-02 BE BE708864D patent/BE708864A/xx unknown
- 1968-01-03 NL NL686800060A patent/NL150664B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH487597A (en) | 1970-03-31 |
| AT293849B (en) | 1971-10-25 |
| DE1642142B2 (en) | 1975-08-07 |
| DE1792760A1 (en) | 1974-05-30 |
| BE708864A (en) | 1968-07-02 |
| DE1642142A1 (en) | 1971-04-22 |
| NO124292B (en) | 1972-04-04 |
| GB1199460A (en) | 1970-07-22 |
| NL6800060A (en) | 1968-07-04 |
| DE1792760C3 (en) | 1978-09-21 |
| NL150664B (en) | 1976-09-15 |
| FR1568003A (en) | 1969-05-23 |
| DE1792760B2 (en) | 1978-01-19 |
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