US3355386A - Germicidal nonionic-detergent iodine compositions - Google Patents
Germicidal nonionic-detergent iodine compositions Download PDFInfo
- Publication number
- US3355386A US3355386A US498130A US49813065A US3355386A US 3355386 A US3355386 A US 3355386A US 498130 A US498130 A US 498130A US 49813065 A US49813065 A US 49813065A US 3355386 A US3355386 A US 3355386A
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- US
- United States
- Prior art keywords
- iodine
- detergent
- ethylene oxide
- color
- complex
- 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
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
- C11D3/485—Halophors, e.g. iodophors
Definitions
- This invention relates to nonionic detergent-iodine complexes which provide enhanced iodine color in use dilutons, and to germicidal compositions contaning such complexes.
- the invention relates to such detergent-iodine complexes wherein a substantial color enhancement is provided by detergent components which are water-soluble condensates of ethylene oxide and a hydroxy compound providing a hydrophobic moiety having an average aliphatic carbon content in the C to C range, and wherein further color enhancement is provided by detergent components having the hydrophobic moiety characterized as above described, but having the ethylene oxide partially replaced or supplemented by propylene oxide.
- iodine use dilutions for cleaning purposes are made at the 25 p.p.m. to 75 ppm. available iodine level. At these levels the iodine color can readily be seen; differences in color as a function of the detergent, measurable by instrument, can hardly be detected by eye and so have never attracted attention. Dilutions at the 12% ppm. level, used exclusively as a sanitizing rinse, have beenonly faintly colored. Since such solutions are used on surfaces that are clean to begin with, there is almost no loss of iodine through reaction with proteinaceous soil, and so the problem of viewing the color as a measure of when replenishment is necessary is not of great importance.
- the new detergent-iodine compositions contain a detergent in which the hydrophobic moiety is a primary aliphatic alcohol, or primary aliphatic alcohol mixture of the C to C and preferably the C to C range.
- a detergent in which the hydrophobic moiety is a primary aliphatic alcohol, or primary aliphatic alcohol mixture of the C to C and preferably the C to C range.
- such alcohols and the detergents formed therefrom are generally not individual compounds, but mixtures characterized by average carbon atom content.
- a commercial C alcohol may itself be a mixture of two, three or more alcohols containing as few as 10 or as many as 20 or more carbon atoms in proportions to average C for the mixture.
- ethylene oxide is condensed with the C to C and preferably C to C alcohols
- the products vary from water insoluble liquids, to Water-soluble Waxes and solids as the amount of condensed ethylene oxide is increased.
- Water solubility, and hence suitability for use as iodine carrier is generally reached when the number of carbon atoms supplied by the ethylene oxide approximately equals or exceeds the number of carbon atoms in the alcohol.
- the number of moles of ethylene oxide should be at least with n being the average number of carbon atoms in the alcohol component.
- a C alcohol condensed with 5 or more moles of ethylene oxide and a C alcohol condensed with 7 or more moles of ethylene oxide will generally'be water-soluble and suitable for use as an iodine carrier.
- the detergent-iodine complex itself be a liquid, although in special instances, as where a dry, powdered composition is desired, it can be a waxy or solid complex. Furthermore, it is possible, although somewhat more difficult, to prepare aqueous liquid concentrates when using waxy or solid detergents. There is therefore, no well defined upper limit to the amount of ethylene oxide which should be condensed with the alcohol. It should be noted,
- the water-soluble alcohol-ethylene oxide condensates can be complexed with iodine by merely mixing together the detergent and elemental iodine at suitably elevated temperatures, i.e., about 50 C. or such higher temperature as is necessary to melt the waxy detergent.
- elevated temperatures i.e., about 50 C. or such higher temperature as is necessary to melt the waxy detergent.
- the complexing can even be effected by room temperature mixing, but the extended time required makes this impractical.
- a preferred method of preparing the complexes is the coldmixing process disclosed in United States Patent No. 3,028,299, wherein iodine is supplied as an aqueous iodide-iodine solution suitably containing about 57% by weight I 20% HI and the balance water. This method is particularly desirable in preparing iodine complexes with waxy or solid alcohol-ethylene oxide condensates.
- the detergent-iodine complexes of the present invention may be employed in germicidal compositions containing amounts of detergent within the range of about 0.5 to'75%, and of available iodine within the range of about 0.1 to 25%.
- Compositions containing about 115% available-iodine and 575% detergent are suitable for products which can be diluted with water when used by a consumer.
- Compositions containing from about 15- 25% available iodine and about 60-75% detergent can be used as manufacturing concentrates.
- Compositions in which the available iodine is from about 0.1 to 1.0% containing about 0.5 to detergent may be suitably used directly without dilution with water.
- the remainder of the composition can be water, or a mixture of water and isopropyl-alcohol.
- a mixture of water with compatible acids it is preferable to employ as added components, a mixture of water with compatible acids.
- compositions When compositions are prepared by the cold method using the above mentioned aqueous HI-iodine solution, the composition will also contain about 1 part of I" to each 3 parts of I Thus, a composition containing 1.5% Is will contain about 0.5% I.
- An important advantage of the new compositions is the superior built-in indicator provided in typical use dilutions of 25 p.p.m., 12.5 p.p.m., and particularly 6 p.p.m. due to the enhanced color of such solutions. It is the practice to instruct customers using detergent-iodine compositions to discard use dilutions when the characteristic iodine color is gone. With many available compositions, however, the color at dilutions as low as 10 to p.p.m., becomes so faint that end point detection becomes difiicult. Such use dilutions are frequently discarded when as much as 50 to 75% of their germicidal activity remains unconsumed.
- the enhanced colorat use dilutions as low as the 5 to 10 ppm. range has been found to be primarily a function of the number of carbon atoms in the primary alcohol which is condensed with ethylene oxide. Best results are obtained with condensates in which the alcohol component has an average of 14 to 18 carbon atoms; and there is a sharp drop-off of color intensity when switching 4 from condensates derived from C to C primary alcohols.
- the color enhancing effectof condensates of C to C primary alcohol with ethylene oxide does not appear to be greatly modified by moderate variation in the ethylene oxide content.
- thenumber of carbon atoms provided by the ethylene oxide should be about equal to, or greater than, the number of carbon atoms in the alcohol.
- the preferred range appears to be about 1 to 2.5 ethylene oxide carbons per primary alcohol carbon.
- Increase in the proportion of detergent to iodine provides a distinct enhancement of color intensity at low use dilutions.
- the color intensity is generally about doubled. This is of special significance in view of the fact that, for compositions with recommended sanitation uses below the 25 p.p.m. iodine level, it is desirable to use progressively higher ratios of detergent to iodine, in order to provide an effective amount of detergent in the more dilute use solutions.
- iodine is superior to dyes in general owing to the small molecular size of iodine compared to dyes; the iodine thereby does not interfere appreciably with the detergent agglomerate.
- a 25 p.p.m. aqueous solution of elemental iodine was used by Ross, to which were added varying amounts of a stock detergent solution. The light absorp-, tion at 360 mg was measured and was plotted as a fling? tion of detergent concentration. The inflection point in' this graph was taken as the crnc yalue. The maximum light absorption in Ross experiments was always found at 360 mu.
- iodide which may be formed in, or added to, the composition. It has been found, for example, that while addition of iodide to a detergent-iodine solution provides some enhancement of color, it is of small magnitude compared to the color change with variations of available iodine concentration. Since iodide alone with detergent produces no color, the color enhancement above mentioned indicates intensifying of color of the detergent-iodine complex in the presence of iodide.
- An effective measure of the iodine complexing in the new detergent-iodine compositions is the distribution coefiicient (D.C.) determined in a two-phase aqueous-heptane system according to the procedure disclosed in the above mentioned United States Patent No. 3,028,229.
- D.C. distribution coefiicient
- cloud point This is the temperature above which detergents and detergent-iodine complexes in aqueous solution change from clear or transparent solutions to cloudy solutions or suspensions.
- the cloud point of liquid germicidal products or concentrates should be at least 50 C., and preferably above about 55 C. in order that such products will remain clear and transparent under all normal storage conditions.
- the unique color enhancing properties as above described for the C to C primary alcohol-ethylene oxide condensates complexed with iodine are also found to be present to a substantial extent in detergent-iodine complexes in which the detergent is a condensate of ethylene oxide with an alkyl phenol in which the alkyl substituent comprises one or more primary aliphatic radicals having a total of 12 to 18 carbon atoms.
- Typical examples of such detergents are condensates of ethylene oxide with dodecylphenol, dioctylphenol, and dinonylphenol in which the amount of ethylene oxide is at' least sufficient to impart water solubility to the detergent.
- the number of moles of ethylene oxide can be in the range of about .8 to 3 times the number of carbon atoms in the alkyl substituent.
- these higher alkyl-phehol-ethylene oxide condensates provide iodine complexes having more than twice the color intensity at 6 p.p.m. available iodine dilutions than complexes formed with the conventional nonylphenol-ethylene oxide condensates.
- Another embodiment of the present invention resides in the discovery that still further color enhancement can be achieved with the primary alcohol type detergents if at least part of the condensed ethylene oxide is replaced with, or supplemented by, ropylene oxide.
- modified detergents can be represented by the following formula:
- R is C to C primary alkyl
- the weight percent of E0 is within the range of 0 to 45% in one of the blocks, x, y and within the range 60 to 100% in the other of the blocks x, y
- the total number of moles of alkoxide is in the range of 6 to 40 moles, with l to 10 moles in the PO rich block, and 5 to 30 moles in the E0 rich block.
- the block x contains 0 to E0, and provides 1 to 4 moles of alkoxide
- the block y contains 60 to 90% E0, and provides 5 to 20 moles of alkoxide.
- Preferred detergents of this modified type provide iodine complexes having under comparable conditions, a color intensity at 6 p.p.m. dilution which is more than four times as great as the conventional nonyl-phenol ethylene oxide-iodine complex. Furthermore, the modified detergents can be in liquid form even when the average number of carbon atoms in the radical R is as high as C Both of these factors are of distinct advantage in the formulation and useof germicidal detergent-iodine compositions.
- Example I A number of detergent iodine compositions were prepared using various primary alcohol-ethylene oxide condensates as detergents. These compositions are all aqueous solutions containing 10% detergent, 1% available iodine, and 0.35% iodide (1*) by weight, the iodine and iodide being supplied as HI-Iodine solution containing 57% available iodine and 20% HI.
- detergents are identified by the number of carbon atoms in the primary alcohol component, the number of moles of condensed ethylene oxide, the cloud point of a 1% aqueous solution, and the physical state at 25 C.
- values are given for distribution coefiicient (D.C.) as determined by the formula:
- I in heptane log for unit path length where I and I are the light in and light out respectively.
- a Beckman Du spectrophotometer with cells of 1.00 cm. path length were used.
- the detergent is a nonyl phenol 20 ethylene oxide condensate widely used in detergent-iodine TABLE B compositions.
- Control B another nonionic detergent extensively used in detergent-iodine compositions is a con- S I Absorbanee at my densate of polyoxypropylene having a molecular weight amp e 7 a 4 V of 17 5,0 with ethylene oxide in an amount to provide 50% 350 3.60 370 380 385 890 400 2 450.
- Sample I is included for comparison purposes to show the poor color obtained when the starting alcohol is below the C -C range.
- the color is most deficient at the levels of 6 and 12.5 p.p.m. available iodine.
- Sample 2 approximately equal to the Control A, represents a combination of minimum length carbon chain in the alcohol moiety and minimal ethylene oxide.
- the preferred samples in Table A are considered to be 8, 9 and 15.
- the detergents in both 8 and 9 are liquids, which as previously indicated, are preferable to solids, and
- Example 11 Relative Color as a Function of Detergent Concentration the detergent of 8 is somewhat more readily available than that of 9. As for sample 15, the disadvantage of the solid form of the detergent is offset by the unusually high color value at the 6 p.p.m. dilution.
- Example III In order to demonstrate the eifect of variation in the proportion of iodide, compositions similar to the preferred samples 8 and 9 of Example I (and here identified as 8b and 9b) were prepared having iodide proportions equal to and approximately four times as great as in Example I, and these compositions at varying dilutions were tested for absorbance with the following results:
- Example IV A commercial high acid detergent iodine composition used for dairy and similar cleaning operations, and having a guaranteed available iodine content of 1.75%, contains by weight 19% detergent (a mixture of 15.7 parts nonyl phenol ethylene oxide condensate containing 10.5 moles of ethylene oxide per mole of nonyl phenol and 3.3 parts of polyoxypropylene condensed with ethylene oxide providing a molecular weight of 1750 in the polyoxypropylene component and 20% of condensed ethylene oxide), 3.3% of HI-iodine (supplied as an aqueous solution containing 57% available iodine and 20% HI) 21.25% of H 'PO (commercial 75% acid) and Water to 100%.
- detergent a mixture of 15.7 parts nonyl phenol ethylene oxide condensate containing 10.5 moles of ethylene oxide per mole of nonyl phenol and 3.3 parts of polyoxypropylene condensed with ethylene oxide providing a molecular weight of 1750 in the polyoxyprop
- the tested samples show generally better cloud points and distribution coefiicients than the control, and of particular significance is the markedly higher absorbance at the practical 12.5 ppm. I use dilution.
- Example V A germicidal detergent-iodine concentrate is prepared by mixing together at room temperature 360 grams of an HI-I solution as described in Example I and 640 This concentrate is suitable for sale and distribution to formulators who will add water, acid, additional detergent, or combinations of these in preparing consumer products. 7
- Examples I to V show the advantages of primary alcohol ethylene oxide condensates as detergent components of detergent-iodine compositoins. The following three examples are included to demonstrate the unsatisfactory nature of secondary alcohol-ethylene oxide condensates.
- Example VI Two of the detergent-iodine compositions of Example 1V, samples and 9c are compared with similar detergent-iodine compositions containing as detergent component Secondary A-a secondary alcohol containing 11 to 15 (average 13) carbon atoms condensed with 9 moles of ethylene oxideand Secondary Ba secondary alcohol containing 11 to 15 (average 13) carbon atoms condensed with 13 moles of ethylene oxide.
- Example IV Since as noted in Example IV this type product should have a guaranteed iodine content of 1.75%, it is apparent that the secondary A and B samples are unsatisfactory, whereas the Sc and 90 samples show very little iodine loss in the accelerated ageing test.
- the two weeks at 125 F. is generally comparable to a full year under normal storage conditions.
- Example VII A typical detergent-iodine composition without phos phoric acid, intended for general environmental sanitation purposes, and having a guaranteed available iodine content of 1.6% contains 15% detergent, 3.3% HI-iodine (supplied as an aqueous solution containing 57% available iodine and 20% HI), 2% of isopropyl alcohol, and water to This type composition was made up using the two preferred detergents from Example I, here identified as 8d and 9d, and the two detergents derived from secondary alcohols, Secondary A and Secondary B as described in Example V, and were tested for available iodine before 1 1 and after the standard two weeks, storage at 125 F., with the following results:
- compositions using ethoxylated secondary alcohols as the detergent component fall below the guaranteed iodine content in the standard accelerated ageing test.
- comparing Examples V and VI serves to indicate that the presence of the phosphoric acid was not a factor, but that the poor results with the ethoxylated secondary alcohols must be due to a chemical instability, i.e. a reactivity between the secondary al-. cohol moiety and the iodine.
- Example VIII Following the conventional formulating procedure of Example IX Following the procedure of Example I an aqueous detergent-iodine solution containing by weight 10% detergent, 1% available iodine and 0.35% iodide (I') using as detergent dodecylphenol condensed with 12 moles of ethylene oxide.
- This detergent is a liquid at C, and in 1% aqueous solution has a cloud point of 60.
- the detergent-iodine solution has a distribution coe f cie f d w e e ted r rel i e color or bsorbance as in Example I, gave results shown in the following tabulation, and compared with the values for Control A from Example 1:
- Relative Color 25 ppm.
- Detergent peak 25 p.p.m. 12.5 ppm. 6 p.p. m.
- This enhancement of color in dilute solutions is characteristic of detergent-iodine compelexes containing as detergent component alkylphenol-ethylene oxide condensates in which primary alkyl substituents provide 12 to 18 car bon atoms, with the color enhancement generally increase ing as the number of carbon atoms is increased.
- I 0 log I 1 cm. of greater than .035, and preferably at least .045 when measured at the 6 ppm. available iodine level with a 10:1 ratio of detergent to iodine.
- Complexes of the three types described which measure up to this characteristic, and have a detergent to available iodine ratio of at least 3:1, and detergent-iodine compositions containing such complexes are considered as falling within the present invention, no matter whether such compositions are in the form of commercial concentrates, consumer products intended for dilution, or end use products adapted for use without dilution.
- a detergent-iodine composition providing enhanced iodine color in high use dilution, said composition consisting essentially of a detergent-iodine complex providing a germicidally effective amount of iodine, the detergent component of said complex being a water soluble primary alcohol-ethylene oxide condensate having an alcoto Zn-l mols of ethylene oxide, where n is the average number of carbon atoms in said alcohol moiety, the ratio of detergent to available iodine in said complex being at least 5:1.
- a detergent-iodine composition providing enhanced iodine color in high use dilution, said composition consisting essentially of a detergent-iodine complex providing a germicidally elfective amount of iodine, the detergent component of said complex being a water soluble alkylphenol-ethylene oxide condensate in which the alkyl substituent comprises one or more primary aliphatic radicals having a total of 12 to 18 carbon atoms, and the number of mols of ethylene oxide is within the range of 0.8 to 3.0 times the number of carbon atoms in said alkyl substituent, the ratio of detergent to available iodine in said complex being at least 5:1.
- a detergent-iodine composition providing enhanced iodine color in high use dilution, said composition consisting essentially of a detergent-iodine complex providing a germicidally effective amount of iodine, the detergent wherein R is C to C primary alkyl, EO and PO represent ethylene oxide and propylene oxide respectively, the Weight percent of E is Within the range of 0 to 45% in one of the blocks x, y and within the range of 60 to 100% in the other of the blocks x, y, and the total number of moles of combined EO and PO is in the range of 6 to 40 moles, with 1 to 10 moles in the PO rich block, and 5 to moles in the E0 rich block, the ratio of detergent to available iodine in said complex being at least 5: 1.
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US498130A US3355386A (en) | 1965-10-19 | 1965-10-19 | Germicidal nonionic-detergent iodine compositions |
IL26644A IL26644A (en) | 1965-10-19 | 1966-10-05 | Germicidal nonionic detergent iodine compositions |
FR80295A FR1500495A (fr) | 1965-10-19 | 1966-10-17 | Compositions iodées de détergents non ioniques, ayant des propriétés germicides |
GB46353/66A GB1167743A (en) | 1965-10-19 | 1966-10-17 | Germicidal Nonionic Detergent-Iodine Preparations |
DE1966W0042607 DE1617238B1 (de) | 1965-10-19 | 1966-10-18 | Detergens-Jod-Zusammensetzung |
BE688428D BE688428A (nl) | 1965-10-19 | 1966-10-18 | |
AT970766A AT287209B (de) | 1965-10-19 | 1966-10-18 | Jodhaltiges Reinigungsmittel |
CH1500066A CH523316A (de) | 1965-10-19 | 1966-10-18 | Nichtionogenes germicides Jod-Detergens |
DK537066AA DK120612B (da) | 1965-10-19 | 1966-10-18 | Desinfektionsmiddel. |
NL6614726.A NL157052B (nl) | 1965-10-19 | 1966-10-19 | Werkwijze voor de bereiding van kiemdodende, niet-ionogene, jodiumhoudende reinigingsmiddelen. |
BR183807/66A BR6683807D0 (pt) | 1965-10-19 | 1966-10-19 | Composicoes de iodo detergente nao ionicas germicidas |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US498130A US3355386A (en) | 1965-10-19 | 1965-10-19 | Germicidal nonionic-detergent iodine compositions |
Publications (1)
Publication Number | Publication Date |
---|---|
US3355386A true US3355386A (en) | 1967-11-28 |
Family
ID=23979709
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US498130A Expired - Lifetime US3355386A (en) | 1965-10-19 | 1965-10-19 | Germicidal nonionic-detergent iodine compositions |
Country Status (11)
Country | Link |
---|---|
US (1) | US3355386A (nl) |
AT (1) | AT287209B (nl) |
BE (1) | BE688428A (nl) |
BR (1) | BR6683807D0 (nl) |
CH (1) | CH523316A (nl) |
DE (1) | DE1617238B1 (nl) |
DK (1) | DK120612B (nl) |
FR (1) | FR1500495A (nl) |
GB (1) | GB1167743A (nl) |
IL (1) | IL26644A (nl) |
NL (1) | NL157052B (nl) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3513098A (en) * | 1967-08-07 | 1970-05-19 | West Laboratories Inc | Germicidal nonionic detergent-iodine compositions |
US3547576A (en) * | 1968-02-26 | 1970-12-15 | Morris I Sheikh | Air sterilization process |
US3914411A (en) * | 1971-03-03 | 1975-10-21 | Produits Ind Cie Fse | Bactericidal solutions containing iodine and a condensation product of propylene oxide and a trialkanalamine |
US3917822A (en) * | 1974-07-29 | 1975-11-04 | Pennwalt Corp | Iodine-containing anionic sanitizers |
US4849215A (en) * | 1983-03-02 | 1989-07-18 | Euroceltique, S.A. | Pharmaceutical iodophor preparations with controlled iodine:iodide ratio and method of producing the same |
US4946673A (en) * | 1984-05-31 | 1990-08-07 | Euroceltique, S.A. | Iodine-containing germicidal preparations and method of controlling germicidal activity |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR3050779B1 (fr) | 2016-04-29 | 2018-11-23 | Poclain Hydraulics Industrie | Systeme de filtration d'un circuit hydraulique comprenant un clapet de derivation |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA540358A (en) * | 1957-04-30 | R. Jackson Donald | Conjugated polyoxypropylene-polyoxyethylene compounds | |
US2868686A (en) * | 1956-11-19 | 1959-01-13 | West Laboratories Inc | Iodine bromine preparations for controlling microorganisms |
US2931777A (en) * | 1956-08-16 | 1960-04-05 | Gen Aniline & Film Corp | Germicidal detergent compositions |
US3028299A (en) * | 1960-09-13 | 1962-04-03 | West Laboratories Inc | Germicidal compositions and methods for preparing the same |
US3029183A (en) * | 1959-05-18 | 1962-04-10 | West Laboratories Inc | Germicidal iodine compositions |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1024660B (de) * | 1953-03-10 | 1958-02-20 | Gen Aniline & Film Corp | Keimtoetendes Reinigungsmittel |
-
1965
- 1965-10-19 US US498130A patent/US3355386A/en not_active Expired - Lifetime
-
1966
- 1966-10-05 IL IL26644A patent/IL26644A/xx unknown
- 1966-10-17 GB GB46353/66A patent/GB1167743A/en not_active Expired
- 1966-10-17 FR FR80295A patent/FR1500495A/fr not_active Expired
- 1966-10-18 DK DK537066AA patent/DK120612B/da unknown
- 1966-10-18 BE BE688428D patent/BE688428A/xx unknown
- 1966-10-18 CH CH1500066A patent/CH523316A/de not_active IP Right Cessation
- 1966-10-18 AT AT970766A patent/AT287209B/de not_active IP Right Cessation
- 1966-10-18 DE DE1966W0042607 patent/DE1617238B1/de not_active Withdrawn
- 1966-10-19 BR BR183807/66A patent/BR6683807D0/pt unknown
- 1966-10-19 NL NL6614726.A patent/NL157052B/nl unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA540358A (en) * | 1957-04-30 | R. Jackson Donald | Conjugated polyoxypropylene-polyoxyethylene compounds | |
US2931777A (en) * | 1956-08-16 | 1960-04-05 | Gen Aniline & Film Corp | Germicidal detergent compositions |
US2868686A (en) * | 1956-11-19 | 1959-01-13 | West Laboratories Inc | Iodine bromine preparations for controlling microorganisms |
US3029183A (en) * | 1959-05-18 | 1962-04-10 | West Laboratories Inc | Germicidal iodine compositions |
US3028299A (en) * | 1960-09-13 | 1962-04-03 | West Laboratories Inc | Germicidal compositions and methods for preparing the same |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3513098A (en) * | 1967-08-07 | 1970-05-19 | West Laboratories Inc | Germicidal nonionic detergent-iodine compositions |
US3547576A (en) * | 1968-02-26 | 1970-12-15 | Morris I Sheikh | Air sterilization process |
US3914411A (en) * | 1971-03-03 | 1975-10-21 | Produits Ind Cie Fse | Bactericidal solutions containing iodine and a condensation product of propylene oxide and a trialkanalamine |
US3917822A (en) * | 1974-07-29 | 1975-11-04 | Pennwalt Corp | Iodine-containing anionic sanitizers |
US4849215A (en) * | 1983-03-02 | 1989-07-18 | Euroceltique, S.A. | Pharmaceutical iodophor preparations with controlled iodine:iodide ratio and method of producing the same |
US4946673A (en) * | 1984-05-31 | 1990-08-07 | Euroceltique, S.A. | Iodine-containing germicidal preparations and method of controlling germicidal activity |
Also Published As
Publication number | Publication date |
---|---|
AT287209B (de) | 1971-01-11 |
CH523316A (de) | 1972-05-31 |
NL157052B (nl) | 1978-06-15 |
BE688428A (nl) | 1967-04-18 |
GB1167743A (en) | 1969-10-22 |
IL26644A (en) | 1970-05-21 |
DE1617238B1 (de) | 1972-03-16 |
BR6683807D0 (pt) | 1973-12-04 |
DK120612B (da) | 1971-06-21 |
FR1500495A (fr) | 1967-11-03 |
NL6614726A (nl) | 1967-04-20 |
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