US2706701A - Process for the preparation of iodinepolyvinylpyrrolidone by dry mixing - Google Patents
Process for the preparation of iodinepolyvinylpyrrolidone by dry mixing Download PDFInfo
- Publication number
- US2706701A US2706701A US282458A US28245852A US2706701A US 2706701 A US2706701 A US 2706701A US 282458 A US282458 A US 282458A US 28245852 A US28245852 A US 28245852A US 2706701 A US2706701 A US 2706701A
- Authority
- US
- United States
- Prior art keywords
- iodine
- polyvinylpyrrolidone
- available
- per cent
- composition
- 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
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/18—Iodine; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/58—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/18—Introducing halogen atoms or halogen-containing groups
- C08F8/20—Halogenation
- C08F8/22—Halogenation by reaction with free halogens
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/16—Halogen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
- C08K3/26—Carbonates; Bicarbonates
Definitions
- This invention relates to an improved process for preparing a dry powdered adduct of iodine and polymeric l-vinyl-2-pyrrolidone (hereinafter called polyvinylpyrrolidone) whereby a stable composition is formed which is readily soluble in water and which provides iodine in readily available and germicidally and bactericidally active form which is essentialy non-toxic to warmblooded animals.
- polyvinylpyrrolidone polymeric l-vinyl-2-pyrrolidone
- this novel i0dine-polyvinylpyrrolidone composition may be prepared by adding a solution of iodine, such as Lugols solution or tincture of iodine to an aqueous solution of polyvinylpyrrolidone.
- compositions of iodine and polyvinylpyrrolidone can be prepared by thoroughly mixing dry elemental iodine with dry powdered polyvinylpyrrolidone.
- the iodine and powdered polymer may be mixed until a homogenous powder is obtained, the mixing being carried out in materials which are not attacked by iodine so as to avoid the introduction of metal ions into the finished composition.
- This mixing may be effected by grinding the iodine and polyvinylpyrrolidone in a mortar and pestle or more advantageously in a suitable mechanical mixer such as a ball mill.
- the time of mixing varies only with the efiiciency thereof, as the combination of the polyvinylpyrrolidone with iodine on its surface is rapid, in fact, such combination will occur to some extent on dropping iodine crystals on the dry powdered polymer.
- the amount of iodine present as iodide ion is determined by reducing the iodine compound in solution with l-N sodium acid sulfite in a NaHSOs, adding enough to make the solution colorless, then adding 0.1-N silver nitrate and enough nitric acid to make the solution acidic and back-titrating with ammonium thiocyanate (NH4SCN).
- the iodide ion is the difference between this figure and the available iodine as determined above.
- the total iodine may be determined by combustion methods such as that formulated by Hallett in Scotts Standard Methods of Chemical Analysis, bound iodine then being determined by substracting the sum of available iodine and iodide ion from the total iodine as determined above.
- the product obtained on mixing polyvinylpyrrolidone and iodine contains a total amount of iodine equal to the amount employed in making the composition and, as stated, this iodine is present as available iodine, iodide ion and bound iodine. It has been found that with any given sample of polyvinylpyrrolidone the amount of bound iodine is constant but that the iodine present as available iodine and iodide ion may vary somewhat. On
- the amount of available iodine slightly decreases which the amount of iodide ion increases. It has been found, however, that a stable product in which the ratio of available iodine to iodide ion is substantially 2:1 is readily and rapidly obtained by heating the dry blended material to a temperature of the order of 100 C. Higher temperatures are preferably avoided in order to avoid degradation of the polymer. Some slight stirring is advantageous during this heating in order to assure a uniform product. It has been found that the heating should be continued until the ratio of available iodine to iodide ion is substantially 2:1. It has been found that before heating one sample, it had a vapor pressure of 0.06 mm. at 55 C. After heating, the product had substantially no vapor pressure at 55 C. Thus, the heating completed the process of formation of a complex in which the iodine is chemically available but not free.
- K value in these examples is meant Fikentscher K value (1000 k) as defined by H. Fikentsober-Cellulosechemie 13, 58-64, 71-4 (1932) and was determined with aqueous solutions of the polymer using an Ubbelohde viscosimeter at 25 C., the concentration being 1 gram of polymer (anhydrous basis) per 100 ml. of solution.
- EXAMPLE I Twelve grams of dry polyvinylpyrrolidone having a K value of 90 (water content about 2 to 3 per cent) was added to 6 grams of solid iodine crystals in a glass bottle containing a few pebbles and beads. This was rolled for three days on a roller mill with occasional manual stirring to loosen the material caked on the sides of the bottle. Analysis showed that the thus obtained product contained 35.4 per cent total iodine and 31.91 per cent available iodine; The material was heat-treated at C. for 64 hours in a closed glass bottle with occasional stirring. On completion of this treatment, analysis showed that the material contained 35.3 per cent total iodine, 25.7 per cent available iodine.
- EXAMPLE II An earthenware crock, having a capacity of one gallon, was charged with 832 grams of dry polyvinylpyrrolidone having a K value of 33 and 168 grams of crystalline iodine broken up in the form of small granules. Enough pebbles, approximately 30, were added to assure eificient mixing. The lid was clamped on tightly and the crock rotated on a roller mill for twenty-four hours. After this period, the mixture was homogenous and no iodine crystals were visible. The material was placed in an oven for eighteen hours at 200 F. (93 C.) with occasional mixing to assure homogeneity.
- the amount of iodine which must be allowed for mixing with any given polymer in order to provide for the bound iodine can readily be determined by simple preliminary tests, i. e., by addition of 0.0l-N iodine solution to an aqueous solution of the polymer and backtitrating with 0.1-N sodium thiosulfate solution using starch as an indicator.
- the iodine which was crude iodine in the form of soft lumps, A" to 1" size, was charged in a 94-gallon ball mill along with 17 pounds of %l" pebbles.
- the iodine was ground for one hour at room temperature, at which time it was found that the iodine was approximately 40-80 mesh size. By visual observation no difference could be noticed in the size of the particles in one hour iodine and the 3-4 hour ground samples.
- the required amount of polyvinylpyrrolidone was then added to the ball mill and blending was continued for six hours at room temperature therein. The ball mill was opened after two hours of mixing and any crystals of iodine found around the gasket were scraped back into the mill.
- the speed of the ball mill for grinding was 16 R. P. M.
- the thus obtained blended polyvinylpyrrolidone iodine composition was placed in dryer trays, one-half full, and heated for a total time of twenty-two hours at a temperature of 95 C. (200 F.) in a closed tray dryer. After six, twelve, and eighteen hours on temperature, the dryer was opened and the trays were stirred with a glass rod. This was done so as to assure uniform product. The total actual heating time was eighteen hours, a total of four hours being consumed in stirring the polyvinylpyrrolidone iodine composition. With each stirring the dryer door was opened slowly to permit more rapid cooling and allowed to cool for twenty minutes. The dryer was then closed, the steam turned on.
- EXAMPLE V 832 parts of polyvinylpyrrolidone having a K value of 36 was charged to a ball mill along with 168 parts of iodine crystals and the mixture blended for six hours, the ball mill being opened after two hours of mixing, at which time any crystals of iodine found around the gasket were scraped back in the mill.
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE615889D BE615889A (ja) | 1952-04-15 | ||
US276449A US2739922A (en) | 1952-03-13 | 1952-03-13 | Mixtures of polymeric n-vinyl pyrrolidone and halogens |
US282458A US2706701A (en) | 1952-04-15 | 1952-04-15 | Process for the preparation of iodinepolyvinylpyrrolidone by dry mixing |
US457777A US2826532A (en) | 1952-04-15 | 1954-09-22 | Process of stabilizing polyvinyl pyrrolidone-iodine compositions |
US603185A US2900305A (en) | 1952-04-15 | 1956-08-09 | Preparation of iodine polyvinylpyrrolidone adducts |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US282458A US2706701A (en) | 1952-04-15 | 1952-04-15 | Process for the preparation of iodinepolyvinylpyrrolidone by dry mixing |
Publications (1)
Publication Number | Publication Date |
---|---|
US2706701A true US2706701A (en) | 1955-04-19 |
Family
ID=23081613
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US282458A Expired - Lifetime US2706701A (en) | 1952-03-13 | 1952-04-15 | Process for the preparation of iodinepolyvinylpyrrolidone by dry mixing |
Country Status (2)
Country | Link |
---|---|
US (1) | US2706701A (ja) |
BE (1) | BE615889A (ja) |
Cited By (83)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2754245A (en) * | 1954-09-23 | 1956-07-10 | Gen Aniline & Film Corp | Interhalogen adducts of polyvinyl pyrrolidone |
US2826532A (en) * | 1952-04-15 | 1958-03-11 | Gen Aniline & Film Corp | Process of stabilizing polyvinyl pyrrolidone-iodine compositions |
US2853416A (en) * | 1955-09-19 | 1958-09-23 | Gen Aniline & Film Corp | Method of protecting plants by applying a pesticidal amount of a polyvinylpyrrolidone-iodine adduct |
US2853417A (en) * | 1955-09-19 | 1958-09-23 | Gen Aniline & Film Corp | Method of controlling plant pests with an iodine adduct of a copolymer of nu-vinyl pyrrolidone and a polymerizable vinyl compound containing one aliphatic double bond |
US2900305A (en) * | 1952-04-15 | 1959-08-18 | Gen Aniline & Film Corp | Preparation of iodine polyvinylpyrrolidone adducts |
US2964447A (en) * | 1956-04-10 | 1960-12-13 | Gen Aniline & Film Corp | Polymer-metal process |
US2987505A (en) * | 1958-03-04 | 1961-06-06 | Gen Aniline & Film Corp | Compositions of polymeric nu-vinyl-2-oxazolidone and halogens |
US3028300A (en) * | 1960-09-13 | 1962-04-03 | West Laboratories Inc | Germicidal compositions and methods for preparing the same |
US3087853A (en) * | 1956-07-02 | 1963-04-30 | Gen Aniline & Film Corp | Water soluble compositions consisting essentially of iodine and a water soluble oxygen containing polymer |
US3133904A (en) * | 1959-05-22 | 1964-05-19 | Dow Chemical Co | Molecular complexes of halogen and cyclic carbamate |
US3136755A (en) * | 1960-12-01 | 1964-06-09 | Gen Aniline & Film Corp | Insoluble polymeric-iodine complexes |
US3437647A (en) * | 1966-02-07 | 1969-04-08 | Gaf Corp | Halogen adducts of alkylated polymers of heterocyclic n-vinyl monomers |
DE2443530A1 (de) * | 1973-09-14 | 1975-03-27 | Ciba Geigy Ag | Desinfektion und entkeimung von muscheln, crustaceen und fischen |
US3898326A (en) * | 1973-05-14 | 1975-08-05 | West Laboratories Inc | Polyvinylpyrrolidone-iodide compositions and polyvinylpyrrolidone-iodide-iodine complexes prepared therefrom |
US4009326A (en) * | 1975-07-31 | 1977-02-22 | Gaf Corporation | Photoconductive polymer and method of manufacture |
US4017407A (en) * | 1973-05-14 | 1977-04-12 | West Laboratories, Inc. | Methods for preparing solid iodine carrier mixtures and solid formulations of iodine with iodine carriers |
US4088597A (en) * | 1977-06-13 | 1978-05-09 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler | Iodophor solution |
US4094967A (en) * | 1976-10-22 | 1978-06-13 | Allor Foundation | Iodine-polyvinylpyrrolidone solid product and method of preparation |
US4125602A (en) * | 1974-12-02 | 1978-11-14 | Ciba-Geigy Corporation | Process for the production of iodophors |
US4200710A (en) * | 1978-04-28 | 1980-04-29 | Basf Aktiengesellschaft | Preparation of polyvinylpyrrolidone-iodine |
US4214059A (en) * | 1978-06-12 | 1980-07-22 | The Purdue Frederick Company | Method for the production of iodophor powders |
US4235884A (en) * | 1978-03-17 | 1980-11-25 | Nicolas Salkin | Method for the preparation of stable aqueous solutions of complexes of polyvinylpyrrolidone and of halogens and the solutions obtained thereby |
US4345049A (en) * | 1979-10-12 | 1982-08-17 | Basf Aktiengesellschaft | Preparation of polyvinylpyrrolidone-iodine |
US4402937A (en) * | 1979-10-18 | 1983-09-06 | Basf Aktiengesellschaft | Preparation of PVP-iodine |
US4521403A (en) * | 1983-01-20 | 1985-06-04 | Simon Gilbert I | Chemotherapeutic method for treating periodontal disease |
US4526751A (en) * | 1983-12-09 | 1985-07-02 | Gartner William J | Germicidal solutions effective for solid surface disinfection |
US4567036A (en) * | 1983-12-30 | 1986-01-28 | Simon Gilbert I | Chemotherapeutic method for treating periodontal disease, and composition therefore |
US4594392A (en) * | 1984-02-13 | 1986-06-10 | Ametek, Inc. - Plymouth Products Division | Synergistically stabilized mixed form halogenated and/or interhalogenated resins for disinfecting water |
US4769013A (en) * | 1982-09-13 | 1988-09-06 | Hydromer, Inc. | Bio-effecting medical material and device |
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 |
DE4013118A1 (de) * | 1989-04-28 | 1990-10-31 | Harbor Ucla Med Ct Res Educat | Povidon-iod-mittel zur ophthalmischen antimikrobiellen prophylaxe bei neugeborenen |
US5152987A (en) * | 1991-10-08 | 1992-10-06 | Isp Investments Inc. | Process for preparing water-insoluble PVP-iodine product |
WO1993006837A1 (en) * | 1991-10-08 | 1993-04-15 | Isp Investments Inc. | Process for preparing pvp-iodine product |
US5616348A (en) * | 1992-09-18 | 1997-04-01 | West Agro, Inc. | Germicidal detergent-iodine compositions including polyvinyl pyrrolidone and compatible nonionic surfactant complexors |
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-
0
- BE BE615889D patent/BE615889A/xx unknown
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- 1952-04-15 US US282458A patent/US2706701A/en not_active Expired - Lifetime
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Cited By (137)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2826532A (en) * | 1952-04-15 | 1958-03-11 | Gen Aniline & Film Corp | Process of stabilizing polyvinyl pyrrolidone-iodine compositions |
US2900305A (en) * | 1952-04-15 | 1959-08-18 | Gen Aniline & Film Corp | Preparation of iodine polyvinylpyrrolidone adducts |
US2754245A (en) * | 1954-09-23 | 1956-07-10 | Gen Aniline & Film Corp | Interhalogen adducts of polyvinyl pyrrolidone |
US2853416A (en) * | 1955-09-19 | 1958-09-23 | Gen Aniline & Film Corp | Method of protecting plants by applying a pesticidal amount of a polyvinylpyrrolidone-iodine adduct |
US2853417A (en) * | 1955-09-19 | 1958-09-23 | Gen Aniline & Film Corp | Method of controlling plant pests with an iodine adduct of a copolymer of nu-vinyl pyrrolidone and a polymerizable vinyl compound containing one aliphatic double bond |
DE1061075B (de) * | 1955-09-19 | 1959-07-09 | Gen Aniline & Film Corp | Verfahren zur Herstellung von loeslichen Additionsprodukten aus Jod und Polymerisaten |
US2964447A (en) * | 1956-04-10 | 1960-12-13 | Gen Aniline & Film Corp | Polymer-metal process |
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