US3663694A - Iodophor dairy sanitants - Google Patents
Iodophor dairy sanitants Download PDFInfo
- Publication number
- US3663694A US3663694A US785331A US3663694DA US3663694A US 3663694 A US3663694 A US 3663694A US 785331 A US785331 A US 785331A US 3663694D A US3663694D A US 3663694DA US 3663694 A US3663694 A US 3663694A
- Authority
- US
- United States
- Prior art keywords
- iodophor
- iodine
- lanolin
- surfactant
- ethoxylated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 235000013365 dairy product Nutrition 0.000 title description 4
- 239000011630 iodine Substances 0.000 abstract description 32
- 229910052740 iodine Inorganic materials 0.000 abstract description 32
- 239000002736 nonionic surfactant Substances 0.000 abstract description 19
- 239000004094 surface-active agent Substances 0.000 abstract description 19
- 239000003795 chemical substances by application Substances 0.000 abstract description 15
- 210000000481 breast Anatomy 0.000 abstract description 14
- 241000283690 Bos taurus Species 0.000 abstract description 6
- -1 HYDROXYL GROUPS Chemical group 0.000 abstract description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract description 2
- BILPUZXRUDPOOF-UHFFFAOYSA-N stearyl palmitate Chemical class CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC BILPUZXRUDPOOF-UHFFFAOYSA-N 0.000 abstract 1
- 239000004166 Lanolin Substances 0.000 description 35
- 229940039717 lanolin Drugs 0.000 description 35
- 235000019388 lanolin Nutrition 0.000 description 35
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 31
- 239000000203 mixture Substances 0.000 description 18
- 241001465754 Metazoa Species 0.000 description 15
- 238000009472 formulation Methods 0.000 description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000009833 condensation Methods 0.000 description 9
- 230000005494 condensation Effects 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- 238000005336 cracking Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 6
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical class CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229940031955 anhydrous lanolin Drugs 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229940035535 iodophors Drugs 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004133 Sodium thiosulphate Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 239000000645 desinfectant Substances 0.000 description 2
- 230000000249 desinfective effect Effects 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000002500 effect on skin Effects 0.000 description 2
- 239000003974 emollient agent Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 229920000847 nonoxynol Polymers 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000002528 anti-freeze Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 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
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 208000004396 mastitis Diseases 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000011012 sanitization Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0041—Mammary glands, e.g. breasts, udder; Intramammary administration
Definitions
- An iodophor udder sanitising agent for cows contains an alkoxylated lanolin derivative in place of part or all of the conventional non-ionic surfactant used heretofore, complexed with iodine. If another non-ionic surfactant is present, it may be a surfactant with or without terminal hydroxyl groups.
- This invention relates to iodophor dairy sanitising agents and particularly iodophor udder sanitising agents.
- An iodophor is a complex of iodine with a non-ionic surface-active agent which makes iodine available for sanitising purposes when in contact with water.
- Iodophor preparations in which a part or all of the elementary iodine content is complexed with non-ionic surfactants are commonly used as sanitising agents in the diary industry. They are used particularly to dip cows udders, in, after milking, to inhibit mastitis.
- iodophor preparations have high bactericidal activity, many of them suifer from the disadvantage that high percentages of ethoxylated surfactants are required for full solubilization of their elementary iodine content; it is recognised that only about 20% of the added iodine is chemically combined with the surfactant, the remainder being titratible analytically with standard sodium thiosulphate solutions.
- a high content of non-ionic surfactant in a conventional iodophor preparation however has strong degreasing properties on the skin. Free elementary iodine also is harsh on the skin.
- non-ionic surfactants are alkoxylated compounds having a free terminal hydroxyl group on the alkoxy chain.
- these surfactants are unsatisfactory for iodophor formulations due to shelf life instability which is presumed to be caused by interaction between iodine and the terminal hydroxyl groups.
- the present invention provides an iodophor udder sanitising agent in which the iodophor consists at least in part of a complex of iodine with a water-soluble alkoxylated lanolin derivative.
- alkoxylated lanolin derivative is meant the product formed by the condensation of an al-kylene oxide and lanolin.
- the alkoxylated lanolin derivative is ethoxylated lanolin which may also be described as the polyethylene oxide derivative of lanolin.
- the use of the polypropylene oxide derivative is also envisaged, and it is a feature of this invention that any water-soluble polyalkylene oxide derivative of lanolin may be used, particularly those having alkyl groups containing 2- 8 carbon atoms.
- the degree of condensation between the lanolin and alkylene oxide is not critical, but will generally be within the range of 6 to 100.
- the preferred average degree of condensation is about moles for ethylene oxide and about to for propylene oxide.
- the invention also provides a method of preparing an iodophor udder sanitising agent which comprises forming a complex of iodine with a water soluble alkoxylated lanolin derivative.
- a non-ionic surfactant other than the alkoxylated lanolin derivatives may also be present, complexed with iodine in the iodophor.
- the alkoxylated lanolin derivative should be mixed with the other non-ionic surfactant before iodine is added. Poo-r stability results if the lanolin derivative is added after iodine has combined with the other non-ionic surfactant.
- the invention further provides a method of disinfecting cows udders which comprises treating the udders with an idophor udder sanitising agent as defined above, usually after dilution of the sanitising agent with water.
- the alkoxylated lanolin derivative is absorbed into the udder dermal tissues, producing an emollient action which succeeds in suppressing teat cracking.
- the lanolin derivative is substansive to the skin of animals, and therefore can take the place of any fact which may be removed by the non-ionic surfactant (if present).
- the sanitising agent may also contain small percentages of an organic acid such as citric acid, propionic acid, tartaric acid or maleic acid.
- the organic acid keeps the pH value on the slightly acid side which is normal for teat tissue where the natural acidity is due to amine acids produced by normal protein degradation.
- the alkoxylated lanolin derivative may make up from 15 to by weight of the total surfactant.
- another non-ionic surfactant it may be a surfactant with or without terminal OH groups.
- Preferred surfactants having terminal OH groups are ethoxylated nonyl phenol and ethoxylated octyl phenol (or nonyl phenol polyethylene glycol ether and octyl phenol polyethylene glycol ether).
- Preferred ethoxylated octyl or nonyl phenols are those which have been produced by the condensation of at least nine molecules of ethylene oxide with the phenol in question. It is possible to use condensation products containing less than nine moles of the ethylene oxide, inasmuch as they do absorb iodine, but these products tend to be more difficult to disperse in water.
- a preferred upper moles condensation ratio for these ethoxylated phenols lies at about 14 molecules of ethylene oxide per mole of phenol.
- An example of a surfactant having no terminal OH groups is that sold under the trade name Texofor ISU by Glovers Chemicals.
- Importance is attached in this invention to the difference between lanolin itself and an alkoxylated lanolin.
- Lanolln is a water-insoluble animal secretion and a complex mixture of fatty compounds and sterols.
- Alkoxylated lanolin is no less complex (after a condensation reaction with a reactive substance such as an alkylene oxide even more complexity of structure might be expected) but is water-soluble.
- the nature of the complex between the iodine and the alkoxylated lanolin is even more difficult to elucidate.
- Iodine is present in at least two forms in the iodophor according to the invention, and to this extent the teaching of, for example, US. Pat. 3,380,923 which makes the assumption that a relative uniform complex, or simple chemical bond, as present is not relevant to the more complex formulation of the present invention.
- the new composition is more bland to the skin than would have been expected from a consideration of the effect of a known iodine/surfactant composition merely soothed with the emollient action of any compatible amount of lanolin.
- Prior art iodophors based on octyl and nonyl phenols have poor storage stability. Their terminal non-aromatic OH groups are eventually reactive with the elementary iodine of the iodophor with the result that thiosulphate titrations of the product over a storage period reveal that the active sanitizing iodine concentration falls ofi? and can produce iodated products which in certain cases can actually be skin irritants.
- iodine does react with non-ionic surfactants such as ethoxylated nonyl and octyl phenols and that iodine losses, in the titratable sense, can be as high as 7% if the product is stored over three months under normal daylight conditions.
- Iodophors containing octyl and nonyl phenols, or any other non-ionic surfactant having a terminal OH group in the alkoxylated chain seem to behave simliarly. It has been found, however, that mixtures of such nonionic surfactants together with alkoxylated lanolin have good storage life; e.g.
- Iodophor sanitising agents normally can have iodine concentrations within the range 0.25 to 2.5%.
- the presence of the lanolin derivative diminishes the dermatological harshness of the elemental iodine and therefore high concentrations of iodine in the range 1.5 to 2.5 can be used.
- concentration of 2% iodine it is found there is no toxicity to the skin.
- iodophors have non-ionic surfactant contents ranging from 5-25%. If iodine-surfactant interaction occurs in any of these products the rate of reaction will be dependent on the concentration of the surfactant and consequently for shelf stability the manufacturer will endeavour to keep the surfactant concentration as low as possible consistent with solubilisation of the iodine. Such products may be sanitising but their detergency will be low. In this particular specification since the problem of shelf stability has been overcome it is possible to produce sanitising detergents with detergent activities as high as 2025%.
- An organic solvent such as an alcohol may be present to control viscosity and endow the product with antifreeze characteristics in countries where low temperatures prevail.
- Unmodified anhydrous lanolin may be included in the formulation to further improve the dermatological properties of the formulation.
- a combination of ethoxylated lanoline and anhydrous unmodified lanolin may be used.
- the invention is illustrated in the following examples of iodophor udder sanitising agents.
- EXAMPLE 1 Ethoxylated lanolin (degree of condensation about 75) 15 lbs.
- EXAMPLE 2 Ethoxylated octyl phenol (about 12 moles ethylene oxide per mole of condensate10 lbs.
- Ethoxylated nonyl phenol may be used in the formulations of Examples 2 and 3 with similar results.
- EXAMPLE 3 A formulation containing 20% by weight of anhydrous lanolin and by weight of:
- EXAMPLE 4 Ethoxylated lanolin (degree of condensation about 75 10 lbs.
- Example 4 the lanolin ethoxylated lanolin formulation may be replaced by a formulation containing 25% anhydrous lanolin and 75% of an alkoxylated fatty alcohol.
- Iodophor of Standard the invention iodophor Control 1. Total number of animals treated 212 197 153 N um- Per- Num- Per- Num- Perber cent her cent ber cent 2. Animals showing teat-cracks at beginning of trial 126 59 106 54. 37 24 3. Animals showing no teat-cracks at beginning of trial 86 41 91 46 116 76 4. Animals showing teat-cracks at end of trial 47 132 67 31 20 5. Animals showing no teat-cracks at end of trial 113 53 65 33 122 80 NOTE.1.
- a method of disinfecting cows udders which comprises contacting the udders with an udder-santising amount of an iodophor comprising a complex of iodine with a surfactant, said surfactant including from to 100% of a water soluble ethoxylated lanolin derivative (formed by a condensation reaction between 6 to 100 molar parts of ethylene oxide with each part of lanolin, whereby the iodophor further acts to reduce teat cracking.
- iodophor also comprises a complex of iodine with a non-ionic surfactant comprising an ethoxylated octyl phenol formed by reaction of from 9 to about 14 moles of ethylene oxide per mole of phenol.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Dairy Products (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB33712/66A GB1144637A (en) | 1966-07-27 | 1966-07-27 | Iodophor dairy sanitising agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3663694A true US3663694A (en) | 1972-05-16 |
Family
ID=10356486
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US785331A Expired - Lifetime US3663694A (en) | 1966-07-27 | 1968-12-19 | Iodophor dairy sanitants |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3663694A (de) |
| AT (1) | AT287210B (de) |
| BE (1) | BE701851A (de) |
| CH (1) | CH496802A (de) |
| DE (1) | DE1642083B1 (de) |
| DK (1) | DK116086B (de) |
| ES (1) | ES343508A1 (de) |
| FR (1) | FR1554654A (de) |
| GB (1) | GB1144637A (de) |
| LU (1) | LU54193A1 (de) |
| NL (1) | NL157504B (de) |
| SE (1) | SE357886B (de) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3903410A (en) * | 1973-04-02 | 1975-09-02 | Harold S Akrongold | Washing polymers |
| US3950261A (en) * | 1975-05-29 | 1976-04-13 | American Cyanamid Company | Anhydrous liquid iodophor solution |
| EP0090205A1 (de) * | 1982-03-15 | 1983-10-05 | Henkel Kommanditgesellschaft auf Aktien | Präparat zur Euterpflege und Zitzendesinfektion bei Milchvieh |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2102751A5 (en) * | 1970-08-20 | 1972-04-07 | Woolcombers Ltd | Chlorinated water-soluble wool grease derivs - -for use as detergents |
| FR2105151B1 (de) * | 1970-09-28 | 1975-01-10 | Standa Laboratoires | |
| FR2201881A1 (en) * | 1972-06-28 | 1974-05-03 | Manoil Jean | Antiseptic creams for cows udders - contg. fat and halogen, protects against bacteria, weather and skin lesions and improves skin suppleness |
| SE7902893L (sv) * | 1979-04-02 | 1980-10-03 | Astra Chem Prod Ab | Desinfektionsmedel |
| NZ204346A (en) * | 1982-05-25 | 1985-10-11 | E S Wilson | Iodophor compositions and use in bovine mastitis control |
| ATE151227T1 (de) * | 1993-04-15 | 1997-04-15 | Ecolab Inc | Iod schutzmittel zum eintauchen der zitzen |
| US7109241B1 (en) | 2000-10-02 | 2006-09-19 | Ecolab, Inc. | Antimicrobial compositions formulated for use in cold temperature conditions and methods of use thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE975834C (de) * | 1950-05-19 | 1962-10-18 | Gen Aniline & Film Corp | Reinigungspraeparat |
-
1966
- 1966-07-27 GB GB33712/66A patent/GB1144637A/en not_active Expired
-
1967
- 1967-07-25 SE SE10831/67*A patent/SE357886B/xx unknown
- 1967-07-25 DE DE19671642083 patent/DE1642083B1/de active Pending
- 1967-07-26 BE BE701851D patent/BE701851A/xx not_active IP Right Cessation
- 1967-07-27 AT AT700967A patent/AT287210B/de not_active IP Right Cessation
- 1967-07-27 FR FR1554654D patent/FR1554654A/fr not_active Expired
- 1967-07-27 CH CH1066067A patent/CH496802A/de not_active IP Right Cessation
- 1967-07-27 LU LU54193D patent/LU54193A1/xx unknown
- 1967-07-27 DK DK387867AA patent/DK116086B/da unknown
- 1967-07-27 NL NL6710423.A patent/NL157504B/xx not_active IP Right Cessation
- 1967-07-27 ES ES343508A patent/ES343508A1/es not_active Expired
-
1968
- 1968-12-19 US US785331A patent/US3663694A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3903410A (en) * | 1973-04-02 | 1975-09-02 | Harold S Akrongold | Washing polymers |
| US3950261A (en) * | 1975-05-29 | 1976-04-13 | American Cyanamid Company | Anhydrous liquid iodophor solution |
| EP0090205A1 (de) * | 1982-03-15 | 1983-10-05 | Henkel Kommanditgesellschaft auf Aktien | Präparat zur Euterpflege und Zitzendesinfektion bei Milchvieh |
| US4466959A (en) * | 1982-03-15 | 1984-08-21 | Henkel Kommanditgesellschaft Auf Aktien | Preparation for udder care and disinfection for dairy animals |
Also Published As
| Publication number | Publication date |
|---|---|
| DK116086B (da) | 1969-12-08 |
| LU54193A1 (de) | 1967-09-27 |
| CH496802A (de) | 1970-09-30 |
| AT287210B (de) | 1971-01-11 |
| DE1642083B1 (de) | 1971-08-26 |
| FR1554654A (de) | 1969-01-24 |
| BE701851A (de) | 1968-01-02 |
| GB1144637A (en) | 1969-03-05 |
| SE357886B (de) | 1973-07-16 |
| NL157504B (nl) | 1978-08-15 |
| ES343508A1 (es) | 1968-12-01 |
| NL6710423A (de) | 1968-01-29 |
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