US3874870A - Microbiocidal polymeric quarternary ammonium compounds - Google Patents
Microbiocidal polymeric quarternary ammonium compounds Download PDFInfo
- Publication number
- US3874870A US3874870A US425931A US42593173A US3874870A US 3874870 A US3874870 A US 3874870A US 425931 A US425931 A US 425931A US 42593173 A US42593173 A US 42593173A US 3874870 A US3874870 A US 3874870A
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- Prior art keywords
- butene
- composition
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- product
- reaction
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
- C08G73/0213—Preparatory process
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
- C08G73/0213—Preparatory process
- C08G73/0226—Quaternisation of polyalkylene(poly)amines
Definitions
- This invention relates to microbiocidal agents, and it particularly relates to microbiocidal agents comprising polymeric quaternary ammonium compounds.
- microorganisms in aqueous systems of the aforesaid type has long been recognized as a particularly burdensome problem since the environment of the aqueous medium itselfis often extremely conducive to rapid multiplication and growth of these undesirable organisms. Only through the rise of carefully tailored microbiocidal agents can this growth and reproduction be reliably controlled without detriment to the process in which the water is used. For example, many times a n X-CH biocidal compound is rendered completely inactive by the particular surrounding media containing the undesirable microorganisms.
- a particular problem in recirculated waters is that the recirculation causes many difficult problems, among which is the gradual build-up and accumulation of undesirable microorganisms in the aqueous fluid. Various bacteria, fungi and algae are favorably produced in such recirculated waters.
- quaternary ammonium biocides Another common feature of quaternary ammonium biocides is that their biocidal effectiveness is diminished in the presence of non-ionic emulsifiers, often to the point where they no longer function as acceptable biocides. This has significantly reduced their possible use in cosmetics and similar preparations that require the inclusion of non-ionic emulsifiers.
- the aforesaid compounds are active against Pseudomonas aeruginosa at a concentration relative to the total composition as low as 25 ppm, although the preferred concentration is about 150 ppm.
- Against Aerohacter acrogenes they are active at a concentration as low as ppm, although the preferred concentration is about 100 ppm.
- Against algae, such as Chlorella pyrenoidosa they are active at a concentration at least as low as 1 ppm and probably even much below that concentration according to present indications.
- the concentration may apparently be increased indefinitely without deleteriously affecting the biocidal activity.
- the products of this invention are effective at a concentration at least as low as about 500 ppm relative to the total composition, and probably at even lower concentrations, according to present indications.
- the preferred range is about I ,000 to 2,000 ppm.
- X is a halogen such as chlorine or bromine and n is an integer from about 2 to 30.
- EXAMPLE 1 14.2 grams of l,4-bis-dimethylamino-Z-butene (0.1 mole) was dissolved in grams of water, and to it was added 12.5 grams (0.] mole) of l,4-dicholoro-2- butene over a period of 15 to minutes while maintaining constant stirring. The reaction was exothermic so that the temperature rose to about 7()C. The reaction mixture was then warmed on a steam bath at a temperature of about C. for about 1 hour, after which the reaction was considered complete. Titration of ionized chlorine was used as a measure of the extent of the reaction and indicated between 98 and 10071 completeness. The reaction product was a viscous material containing about 50% active material.
- the compounds of this invention may be obtained directly as crystalline-like solids when the reaction is carried out in certain organic solvents such isopropanol, acetone and inert halogenated solvents. This is illustrated as follows:
- EXAMPLEZ 14.2 grams of l,4-bis-dimethylamino-2-butene were mixed with 25 grams of isopropanol, and to it was added, with stirring. 12.5 grams of 1.4-dichloro-2- butene over a period of about minutes (or at a rate which keeps the solvent gently refluxing). After the exothermic reaction subsided, the mixture was warmed on a ateam bath to reflux temperature and maintained at such temperature for about 1 hour. It was then cooled, to room temperature, whereby a precipitate was formed. The precipitate was then separated out by filtration as the final product. The precipitate weighed 18.7 grams. This product is substantially free from impurities caused by side reactions or due to absorption of unreactcd starting materials, thereby making it easier to purify for use in cosmetics or cosmetic emulsions.
- Solid products of the above type have the commercial advantage over aqueous solutions or dispersions because they have less bulk on a pound for pound active ingredient basis.
- EXAMPLE 4 142 grams of l,4'bis-dimethylamino-2-butcne were dissolved in 300 ml. of 1,1 ,l-trichloroethane and to it was added slowly, with constant stirring, 125 grams of l ,4-dichloro-2-butenc at a rate which kept the reaction mixture at a temperature between 45 and 60C., and stirring was continued at 45 to 60C. for 1 hour after an almost-white precipitate was first deposited. After cooling, the precipitate wascollected by filtration and dried in a vacuum desiccator. ltwcighed 245 grams.
- EXAMPLE 8 14.2 grams of 1,4-bis-dimethylamino-2-butene (0. 1 mole) was dissolved in grams of water, and wit was added 37.5 grams of 1,4-dichloro-2-butene over a period of 1530 minutes, maintaining constant stirring.
- reaction was exothermic. After one hour, analysis for ionic chloride showed that the reaction was about 9894 complete.
- EXAMPLE 9 EXAMPLE 10 The same reactants and procedures as used in Example 8, but using 45 grams of aceton'einstead of water gave a solid product which weighed 21.4 grams after filtration.
- Example 1 1 The same reactants and procedures used in Example 1 1 were used with 20 grams of isopropyl alcohol as sol vent instead of water. After about 1 hour, the. solid f polymeric product was filtered off. It weighed. 9.4
- EXAMPLE 13 The same reactants and procedures as used in Exam ple 1 1 were used, except that 20 grams of acetone replaced water as solvent. After about 1 hour, the product weighed about 10.7 grams.
- EXAMPLE 14 21.3 grams of 1,4-bis-dimethylamino-2-butene was (0.15 moles) dissolved in 25 grams of water, and to it was added 6.3 grams of 1,4-dichloro-2-butene (0.05 moles) over a period of 15-30 minutes, maintaining constant stirring. After 1 hour, analysis for ionic ch1o-- ride showed about 9871 completion.
- EXAMPLE 16 The same reactants used in Example 14, but with 25 1 grams of acetone replacing water as solvent, produced about 10.7 grams of solid polymeric product.
- test concentration l. ml. volume of the product of Example 1 (here? inafter referred to as product A) was diluted in distilled water to the test concentration, and was added asceptically to previously sterilized cotton-stoppered 125 ml. Erlenmeyer flasks.
- product B another known microbiocidal polymeric quaternary ammonium compound, namely a product produced by the reaction of bis(2-chlorocthyl) ether and tetramethyl ethylenediamine
- test flasks were each inoculated with 0.5 ml. of a 1/10 nutrient broth dilution of a 24-hour nutrient broth culture of Aerobactcr aerogenes and another set of test flasks were each inoculated with 0.5 ml. of a one-tenth nutrient broth dilution of a 24-hour nutri ent broth culture of Pseudomonas aeruginosa.
- Agar plate counts were prepared from 10 and 10 dilutions.
- a graduated blender cylinder is rinsed with distilled water. ml, of aqueous test solution is added downthe walls of the blender so as to cause no foam. the blender is turned to high speed for exactly 5 seconds, and upon turning the blades off, timing is started with a stop watch, and at the same time the foam height read in mm. from the 100 ml. mark.
- the foam half-life is defined as the time it takes for liquid to drain out of the foam and reach the 50 ml. mark.
- CYLINDER SHAKE TEST I ml. of test solution is gently poured down the walls of a 250 ml. graduated cylinder that has a glass stopper. The cylinder is stoppered and inverted times in 15 seconds, finally resting it in an upright position. The foam height is read in cc. from the base of the foam.
- Example I8 Components 71 by Wt. I by by Wt. "/r by Wt.
- the mineral oil, lanolin, cetyl alcohol, Tween 80, and Span 80 were combined and heated to about (157()C.
- the water was heated to about 7()C. and added slowly to the hot non-aqucousphase while stirring the mixture until it emulsified completely.
- the emulsion was cooled to room temperatureusing con-. tinued agitation.
- Table 1 1 Count Count Count Count cck INOCULATION at 3.1"1 l0 organisms/ml. ot' jar content for each i 40 of the four formulations of Example 21: 1 10x10- 10x10" 10x10" 4x10" 3 98x10" 13x10" 1 1X10" 5X10" Count Count Count Count 1 07x10" 40x10 24x10 10x10" COR 4 142x10" lt)2 84x10" 01x10" 5 167Xl0" l19 l0 X4Xl0" (17 l0 l ZZXIU 19X 10 l7 l0"' l5 l0 6 180x10" l 14 10 32x11)" 44x11)" 2 P.4Xl0 21x11)" 19 l0 l -l l0 7 140x10" 95x10 82x10" 70x10" 3 80x10" 71x10" 94
- Cetyl alcohol 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0
- a method of controlling the proliferation of deleterious microorganisms selected from the group consisting of bacteria and algae in an aqueous system which comprises applying to said microorganisms a hacteriacidally or algaecidally effective amount of a condensation product formed'by mixing l,4-bisdimethylamino-Z-butene dissolved in a solvent with 1,4- dihalo-Z-butene at room temperature whereby an exothermic reaction is obtained causing the temperature of the mixture to rise, then maintaining the mixture at no higher than reflux temperature until the reaction is LII complete, wherein these reactants arepresent ina molar proportion of between about 1:3 and about 321 relative to each other.
- said agent being present in a bacteriacidally or algaecidally effective amount.
- composition of claim 5 wherein said aqueous media comprises recirculating water.
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- Polymers & Plastics (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
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Abstract
Description
Claims (8)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US425931A US3874870A (en) | 1973-12-18 | 1973-12-18 | Microbiocidal polymeric quarternary ammonium compounds |
US495328A US3929990A (en) | 1973-12-18 | 1974-08-07 | Microbiocidal polymeric quaternary ammonium compounds |
US510617A US3923973A (en) | 1973-12-18 | 1974-09-30 | Fungicidal polymeric quaternary ammonium compounds |
US511759A US3928323A (en) | 1973-12-18 | 1974-10-03 | Anti-microbial quaternary ammonium co-polymers |
US05/565,839 US4025627A (en) | 1973-12-18 | 1975-04-07 | Microbiocidal polymeric quaternary ammonium compounds |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US425931A US3874870A (en) | 1973-12-18 | 1973-12-18 | Microbiocidal polymeric quarternary ammonium compounds |
Related Child Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US47852474A Continuation-In-Part | 1973-12-18 | 1974-06-12 | |
US48696074A Continuation-In-Part | 1974-07-10 | 1974-07-10 | |
US495328A Continuation-In-Part US3929990A (en) | 1973-12-18 | 1974-08-07 | Microbiocidal polymeric quaternary ammonium compounds |
US511759A Continuation-In-Part US3928323A (en) | 1973-12-18 | 1974-10-03 | Anti-microbial quaternary ammonium co-polymers |
Publications (1)
Publication Number | Publication Date |
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US3874870A true US3874870A (en) | 1975-04-01 |
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US425931A Expired - Lifetime US3874870A (en) | 1973-12-18 | 1973-12-18 | Microbiocidal polymeric quarternary ammonium compounds |
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US (1) | US3874870A (en) |
Cited By (406)
Publication number | Priority date | Publication date | Assignee | Title |
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FR2307856A1 (en) * | 1975-04-14 | 1976-11-12 | British Petroleum Co | POLYMER COMPOSITION FORMING A FILM AND USED AS A PAINT PREVENTING FOULING BY MARINE ORGANISMS |
US4025617A (en) * | 1974-10-03 | 1977-05-24 | Millmaster Onyx Corporation | Anti-microbial quaternary ammonium co-polymers |
US4155994A (en) * | 1977-01-21 | 1979-05-22 | Kewanee Industries, Inc. | Hair conditioning agents |
US4157388A (en) * | 1977-06-23 | 1979-06-05 | The Miranol Chemical Company, Inc. | Hair and fabric conditioning compositions containing polymeric ionenes |
US4197865A (en) * | 1975-07-04 | 1980-04-15 | L'oreal | Treating hair with quaternized polymers |
US4209397A (en) * | 1979-01-31 | 1980-06-24 | Kewanee Industries | Flocculants for aqueous systems |
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US4381919A (en) * | 1975-07-04 | 1983-05-03 | Societe Anonyme Dite: L'oreal | Hair dye composition containing quaternized polymers |
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