US2541248A - Compositions - Google Patents

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US2541248A
US2541248A US2541248DA US2541248A US 2541248 A US2541248 A US 2541248A US 2541248D A US2541248D A US 2541248DA US 2541248 A US2541248 A US 2541248A
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    • BPERFORMING OPERATIONS; TRANSPORTING
    • B65CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
    • B65DCONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
    • B65D81/00Containers, packaging elements, or packages, for contents presenting particular transport or storage problems, or adapted to be used for non-packaging purposes after removal of contents
    • B65D81/18Containers, packaging elements, or packages, for contents presenting particular transport or storage problems, or adapted to be used for non-packaging purposes after removal of contents providing specific environment for contents, e.g. temperature above or below ambient
    • B65D81/22Containers, packaging elements, or packages, for contents presenting particular transport or storage problems, or adapted to be used for non-packaging purposes after removal of contents providing specific environment for contents, e.g. temperature above or below ambient in moist conditions or immersed in liquids
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N33/00Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02Amines; Quaternary ammonium compounds
    • A01N33/12Quaternary ammonium compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/13Amines
    • A61K31/14Quaternary ammonium compounds, e.g. edrophonium, choline
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2300/00Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00

Definitions

  • This invention relates to packaged germicides and compositions for general germicidal purposes which may be packaged and utilized Widely for general disinfecting, deodorizing, sanitizing, sterilizing and similar utilities.
  • Quaternary ammonium salts have been suggested for use for germicidal and. insecticidal purposes.
  • Exemplary of such compounds is cetyl trimethyl ammonium bromide commercially known as CTAB and the related derivative called Ethyl CTAB.
  • CTAB cetyl trimethyl ammonium bromide
  • Ethyl CTAB the related derivative of Ethyl CTAB.
  • Such compounds while having valuable properties for germicidal purposes possess undesirable physical properties from the standpoint of merchandising in that they pack' very tightly and .become Water-insoluble due to compression. Consequently they have been marketed in the form of solutions, as for example, solutions in water. Distribution of such liquids is unsatisfactory as a commercial proposition.
  • V the preparation of solid mixtures containing quaternary ammonium salts which do not pack in the sense of caking, and under ordinary com pression do not become water-insoluble. 7
  • compositions of such quaternary ammonium compounds include packaged compositions of such quaternary ammonium compounds.
  • the quaternary ammonium compounds are used in admixture with water-soluble, non-packing solid adjuvants which serve the purpose of preventing the quaternary ammonium compound from packing or .caking so that the resulting compositions retain their desirableproperties of being readily disseminated and dissolved in solvents such as water.
  • solvents such as water.
  • such compositions lend themselves-to packaging and packagesmay be made of sealed containers containing any desired amounts of such compositions which being in dry form, may be readily distributed or shipped without difficulty. During such shipment they do not pack or compress or cake and are directly available without furtherpreparation for solution in water or other solvent for use.
  • the quaternary ammonium. compounds utilized for this purpose are more desirably the solid,
  • quaternary ammonium salts and related compounds possessing the desired germicidal or disinfecting or sterilizing properties. While the quaternary ammonium salts and re lated compounds may vary greatly and maybe any of the organo group substituted quaternary ammonium salts and related compounds which may be generally formulated as follows.
  • the organic groups may be aliphatic such as alkyl or olefinic, alicyclic and carbocyclic such as aryl or cycle aliphatic, etc., as Well as the stated organo groups containing substituents for example, the halogens such as chlorine, bromine, iodine, nitro groups, amino groups, carboxy groups, ether groups, etc.
  • organic groups there maybe mentioned methyl, ethyl, propyl, butyl, lauryl, dodecyl, stearyl, allyl, .phenyl, tolyl, benzyl and other aralkyl and alkaryl groups, cyclohexyl, acetonyl, hydroxy ethyl, oxy methyl, diethylbeta hydroxy gamma butyl oxy propyl, thioethyl, glycido, geranyl, nitro-benzyl, trihydroxy ethyl, etc.
  • the anionic group may be any salt forming group including the halides such as chloride, bromide and iodide, and other groups including the nitrates, sulfates, alkyl sulfates, phosphates, organic acid radicals, such as formates, acetates, lactates, tartrates, citrates, aryl sulfonic acids such as benzene sulfonate or toluene sulfonate,
  • halides such as chloride, bromide and iodide
  • other groups including the nitrates, sulfates, alkyl sulfates, phosphates, organic acid radicals, such as formates, acetates, lactates, tartrates, citrates, aryl sulfonic acids such as benzene sulfonate or toluene sulfonate,
  • the tetra-organo substituted quaternary am monium compounds that is, those compounds which contain four organo groups attached to the nitrogen are the preferred compounds utilized in accordance with the present invention and more particularly where one of the organo groups is a long chain aliphatic radicalv having more than '7 carbon atoms, such as the lauryl group referred to above or other of the higher groups and preferably one of the organo groups in the, tetra substituted quaternary ammonium salts" will be of that character, the other groups being either alkyl, aryl, aralkyl such as benzyl, etc.
  • the chlorides or bromides are employed since they are readily available and these compounds will be utilized to illustrate the invention.
  • g mem r-so u l non-p king solid adiuva t which is employed desirably of non-hygroscopic character may be inorganic and includes generally the water-soluble inorganic bases, acids, and salts, the salts employed being those which are either neutral, acid or basic salts, and particularly the salts of the alkali metals including sodium, potassium, ammonium, etc.
  • Exemplary salts are those of the inorganic polybasic acids specifically carbonatesphosphates, borates, sulfates, sulfites and the like, illustrated specifically by sodium bicarbonate, trisodium phosphate, borax, sodium sulfate, sodium bisulfate, etc.
  • Illustrative of the inorganic water-soluble bases are the caustic alkalies such as sodium hydroxide.
  • Water-soluble organic compounds may also be used to be mixed with the quaternary ammonium compound. They should be non-hygroscopic and must not pack or cake when mixed with the quaternary ammonium compound. They may be salts such as sodium acetate, etc., phenates such as sodium phenate, water-soluble amines such as *urea; etc. In water solution they may be either acid' or alkaline.
  • the proportions of the quaternary ammonium salt "to water-soluble solid adjuvant may vary over wide limits depending on the nature of the quaternary ammonium salt and the solid ad- ;iuvant employed. All that is required is that there should-be a sufificient amount of the nonpacking or non-caking solid adjuvant in the mixture, to prevent the packing or caking of the quaternary ammonium salt. As a general rule the amounts employed will run from about 20% to of quaternary ammonium salt to 80% to 20% 'c f fthej'solida'djuvant and ratios of 50% of quaternary ammonium salt to 50% of solid adjuvant may be readily utilized.
  • the solid quaternary amfmonium compounds are desirably employed.
  • the liquid quaternary ammonium icompounds may be utilized where admixture with the organic solid adjuvant gives a resulting solid composition that retains its property of readily distributing, disseminating, or dissolving in water "or other "desired solvent.
  • compositions maybe dissolved in water or organic solvents at room temperatures or higher temperatures such as from 40 to 70 F. and used for germicidal or bactericidal or similar purposes. If desired, however, they may be utilized at highertemperatures as from 70 F. to 170 F. particularly where sterilization is desired.
  • compositions produced as set forth above may be re'adilypackagd by taking the solid'mixture placing it in any desired container such as a cardboard capsule which may be readily sealed. 'Such compositions may be shipped as desired and retain their desired physical properties, do not .cake in the package, and do not lose their watersolubility.
  • compositions thus produced are widely useful for general disinfecting, deodoriz'ing, sanitizing and sterilizing. They may be utilized for solution in water to sterilize urgical instruments, sickro'o ,tablewear, linen,- and all-kinds of .appaints: and equipment where sterilization is desired; they may be added to, various substances such as case-inpaints, glue, and other paste, powder and liquid. products to which they give the preservative and deodorizing powers derived from the composition, only small'quantities of the.
  • these compositions may be utilized together with necessary tableting adjuvants to produce tableted material which can be utilized for solution in water to make an odorless harmless germicide and deodorant for a variety of uses.
  • non-cakcaking or non-packing compositions as set forth above all that is required is that some solid adhesive material of the ordinary type employed for tableting purposes be incorporated into the composition to make the powdery materials adhere sufficiently to form a tablet under the pressures employed in the usual tableting machines and there is also desirably included a small amount of a mold lubricant particularly a solid mold lubricant commonly used for producing good tablets in such operations.
  • a mold lubricant particularly a solid mold lubricant commonly used for producing good tablets in such operations.
  • solid adhesives that can be employed any of those normally used in tableting such as pharmaceutical compositions can be utilized and such solid adhesives are represented by the various starches including ordinary cornstarch, and the various gums and resins particularly solid water-soluble gums.
  • metallic soaps such as the stearates or other metal salts particularly alkali metal salts of the higher fatty acids.
  • the adhesives may be present in the composition in amounts as desired and may run to 50% or more of the composition, while only a small amount of lubricant is necessary.
  • non-caking and non-packing compositions produced above may be tableted under sufiicient pressures without necessarily including any adhesive and lubricant as set forth although the latter are desirably employed as indicated;
  • asealed container containing ethyl cetyl dimethyl ammoni which prevents packing of the saltso that the 5 ethyl cetyl dimethyl ammonium bromide remains readily water-soluble, and the ratio of ethyl cetyl dimethyl ammonium bromide to adjuvant being from 1:4 to 4:1.

Description

Patented Feb. 13, 1951 OFFICE PACKAGED GERMICIDES AND COMPOSITIONS Ralph M..Hibbs, Philadelphia, Pa.
No Drawing. Application January 23, 1947, Serial No. 723,897
3 Claims. (01. 16722) This invention relates to packaged germicides and compositions for general germicidal purposes which may be packaged and utilized Widely for general disinfecting, deodorizing, sanitizing, sterilizing and similar utilities.
Quaternary ammonium salts have been suggested for use for germicidal and. insecticidal purposes. Exemplary of such compounds is cetyl trimethyl ammonium bromide commercially known as CTAB and the related derivative called Ethyl CTAB. Such compounds while having valuable properties for germicidal purposes possess undesirable physical properties from the standpoint of merchandising in that they pack' very tightly and .become Water-insoluble due to compression. Consequently they have been marketed in the form of solutions, as for example, solutions in water. Distribution of such liquids is unsatisfactory as a commercial proposition.
Among the objects of the present invention is V the preparation of solid mixtures containing quaternary ammonium salts which do not pack in the sense of caking, and under ordinary com pression do not become water-insoluble. 7
Further objects include packaged compositions of such quaternary ammonium compounds.
Still further objects and advantages of the present invention will appear from the more detailed description set forth below, it being understood that such detailed description is given by way of illustration and explanation only, and not by way of limitation, since various changes therein may be made by those skilled in the art, without departing from the scope and spirit of the present invention.
In accordance with the present invention the quaternary ammonium compounds are used in admixture with water-soluble, non-packing solid adjuvants which serve the purpose of preventing the quaternary ammonium compound from packing or .caking so that the resulting compositions retain their desirableproperties of being readily disseminated and dissolved in solvents such as water. Further, such compositions lend themselves-to packaging and packagesmay be made of sealed containers containing any desired amounts of such compositions which being in dry form, may be readily distributed or shipped without difficulty. During such shipment they do not pack or compress or cake and are directly available without furtherpreparation for solution in water or other solvent for use.
. The quaternary ammonium. compounds utilized for this purpose are more desirably the solid,
water-soluble quaternary ammonium salts and related compounds possessing the desired germicidal or disinfecting or sterilizing properties. While the quaternary ammonium salts and re lated compounds may vary greatly and maybe any of the organo group substituted quaternary ammonium salts and related compounds which may be generally formulated as follows.
. R R2 R6? in which R is an .Qrgano group, R1, BzandRs are either hydr en or ream gr ups, and X is an anionic group.' The organic groups may be aliphatic such as alkyl or olefinic, alicyclic and carbocyclic such as aryl or cycle aliphatic, etc., as Well as the stated organo groups containing substituents for example, the halogens such as chlorine, bromine, iodine, nitro groups, amino groups, carboxy groups, ether groups, etc. As exemplary of such organic groups there maybe mentioned methyl, ethyl, propyl, butyl, lauryl, dodecyl, stearyl, allyl, .phenyl, tolyl, benzyl and other aralkyl and alkaryl groups, cyclohexyl, acetonyl, hydroxy ethyl, oxy methyl, diethylbeta hydroxy gamma butyl oxy propyl, thioethyl, glycido, geranyl, nitro-benzyl, trihydroxy ethyl, etc. The anionic group may be any salt forming group including the halides such as chloride, bromide and iodide, and other groups including the nitrates, sulfates, alkyl sulfates, phosphates, organic acid radicals, such as formates, acetates, lactates, tartrates, citrates, aryl sulfonic acids such as benzene sulfonate or toluene sulfonate,
benzoates, salicylates, etc.
The tetra-organo substituted quaternary am monium compounds, that is, those compounds which contain four organo groups attached to the nitrogen are the preferred compounds utilized in accordance with the present invention and more particularly where one of the organo groups is a long chain aliphatic radicalv having more than '7 carbon atoms, such as the lauryl group referred to above or other of the higher groups and preferably one of the organo groups in the, tetra substituted quaternary ammonium salts" will be of that character, the other groups being either alkyl, aryl, aralkyl such as benzyl, etc. Preferably the chlorides or bromides are employed since they are readily available and these compounds will be utilized to illustrate the invention. g mem r-so u l non-p king solid adiuva t which is employed desirably of non-hygroscopic character may be inorganic and includes generally the water-soluble inorganic bases, acids, and salts, the salts employed being those which are either neutral, acid or basic salts, and particularly the salts of the alkali metals including sodium, potassium, ammonium, etc. Exemplary salts are those of the inorganic polybasic acids specifically carbonatesphosphates, borates, sulfates, sulfites and the like, illustrated specifically by sodium bicarbonate, trisodium phosphate, borax, sodium sulfate, sodium bisulfate, etc. Illustrative of the inorganic water-soluble bases are the caustic alkalies such as sodium hydroxide.
Water-soluble organic compoundsmayalso be used to be mixed with the quaternary ammonium compound. They should be non-hygroscopic and must not pack or cake when mixed with the quaternary ammonium compound. They may be salts such as sodium acetate, etc., phenates such as sodium phenate, water-soluble amines such as *urea; etc. In water solution they may be either acid' or alkaline.
..The proportions of the quaternary ammonium salt "to water-soluble solid adjuvant may vary over wide limits depending on the nature of the quaternary ammonium salt and the solid ad- ;iuvant employed. All that is required is that there should-be a sufificient amount of the nonpacking or non-caking solid adjuvant in the mixture, to prevent the packing or caking of the quaternary ammonium salt. As a general rule the amounts employed will run from about 20% to of quaternary ammonium salt to 80% to 20% 'c f fthej'solida'djuvant and ratios of 50% of quaternary ammonium salt to 50% of solid adjuvant may be readily utilized.
As pointed out above, the solid quaternary amfmonium compounds are desirably employed. In some cases the liquid quaternary ammonium icompounds may be utilized where admixture with the organic solid adjuvant gives a resulting solid composition that retains its property of readily distributing, disseminating, or dissolving in water "or other "desired solvent.
. The resulting compositions maybe dissolved in water or organic solvents at room temperatures or higher temperatures such as from 40 to 70 F. and used for germicidal or bactericidal or similar purposes. If desired, however, they may be utilized at highertemperatures as from 70 F. to 170 F. particularly where sterilization is desired.
Compositions produced as set forth above may be re'adilypackagd by taking the solid'mixture placing it in any desired container such as a cardboard capsule which may be readily sealed. 'Such compositions may be shipped as desired and retain their desired physical properties, do not .cake in the package, and do not lose their watersolubility.
The compositions thus produced are widely useful for general disinfecting, deodoriz'ing, sanitizing and sterilizing. They may be utilized for solution in water to sterilize urgical instruments, sickro'o ,tablewear, linen,- and all-kinds of .appaints: and equipment where sterilization is desired; they may be added to, various substances such as case-inpaints, glue, and other paste, powder and liquid. products to which they give the preservative and deodorizing powers derived from the composition, only small'quantities of the.
utilized elnthe manner set forth-above.- The con-.
2,541,248 l. 'i I carbonate, by weight, or 50% Ethyl CTAB with 50% sodium bicarbonate. Or 60% of the stated quaternary ammonium compound may be used with 40% of sodium bicarbonate or of sodium acetate. Mixtures of organic and inorganic ad- ..juvants may be made with the quaternary ami monium compound or compounds and used as set forth herein. The compositions may be mixed intimately in any desired way and then packaged in the manner set forth above.
Since the inclusion of the water-soluble nonpacking adjuvant prevents the quaternary compound from packing and caking to a condition where it becomes water-insoluble, these compositions may be utilized together with necessary tableting adjuvants to produce tableted material which can be utilized for solution in water to make an odorless harmless germicide and deodorant for a variety of uses. With the non-cakcaking or non-packing compositions as set forth above all that is required is that some solid adhesive material of the ordinary type employed for tableting purposes be incorporated into the composition to make the powdery materials adhere sufficiently to form a tablet under the pressures employed in the usual tableting machines and there is also desirably included a small amount of a mold lubricant particularly a solid mold lubricant commonly used for producing good tablets in such operations. As the solid adhesives that can be employed any of those normally used in tableting such as pharmaceutical compositions can be utilized and such solid adhesives are represented by the various starches including ordinary cornstarch, and the various gums and resins particularly solid water-soluble gums. As mold lubricants there are generally employed metallic soaps such as the stearates or other metal salts particularly alkali metal salts of the higher fatty acids. The adhesives may be present in the composition in amounts as desired and may run to 50% or more of the composition, while only a small amount of lubricant is necessary.
As exemplary of such compounds that may be formulated and converted into tablets for use .in this way, the following is given. 5% ethyl cetyl dimethyl ammonium bromide, 40% bicarbonate of soda, 40% starch, and 5% calcium stearate, Another example is 15% ethyl cetyl dimethyl ammonium bromide, 60% sodium borate, 15% calcium stearate, 10% acacia pulvis. A further example is 20% ethyl cetyl dimethyl ammonium -bromide, 5% propylene glycol, 75 .sodium meta phosphate. A still further exampleis 25% ethyl cetyl dimethyl ammonium bromide, '70% disodium phosphate, 5% talc.
As a matter of fact some of the non-caking and non-packing compositions produced above may be tableted under sufiicient pressures without necessarily including any adhesive and lubricant as set forth although the latter are desirably employed as indicated;
f Having thus set forth my invention, I claim:
l- As an article-of manufacture, asealed container containing ethyl cetyl dimethyl ammoniwhich prevents packing of the saltso that the 5 ethyl cetyl dimethyl ammonium bromide remains readily water-soluble, and the ratio of ethyl cetyl dimethyl ammonium bromide to adjuvant being from 1:4 to 4:1.
2. The article of claim 1, in which the adjuvant is sodium bicarbonate, the materials being present in equal parts byweight.
3. The article of claim 1 in which the adiuvant is sodium acetate, the materials being present 15 in equal parts by weight.
RALPH M. HIBBS.
6 REFERENCES CITED The following references are of record in the f le of this patent:
UNITED STATES PATENTS Number Name Date 1,785,327 Ostromislensky Dec. 16, 1930 2,060,850 Calcott Nov. 17, 1936 1,176,896 Epstein Oct. 24, 1939 10 2,191,678 Nitardy Febj27, 1940 2,200,603 Hentrich May 14, 1940 22,281,786 Mohr May 5, 1942 "2,295,504 Shelton Sept. 8, 1942 1,479,850 Marks Aug. 23, 1949 FOREIGN PATENTS Number Country Date 505,429 Great Britain May 1, 1939

Claims (1)

1. AS AN ARTICLE OF MANUFACTURE, A SEALED CONTAINER CONTAINING ETHYL CETYL DIMETHYL AMMONIUM BROMIDE WHICH NORMALLY PACKS, IN ADMIXTURE WITH AN AMOUNT OF A WATER-SOLUBLE NON-PACKING SOLID ADJUVANT SELECTED FROM THE GROUP CONSISTING OF SODIUM BICARBONATE AND SODIUM ACETATE WHICH PREVENTS PACKING OF THE SALT SO THAT THE ETHYL CETYL DIMETHYL AMMOMIUM BROMIDE REMAINS READILY WATER-SOLUBLE, AND THE RATIO OF ETHYL CETYL DIMETHYL AMMONIUM BROMIDE TO ADJUVANT BEING FROM 1:4 TO 4:1.
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Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2676955A (en) * 1950-10-21 1954-04-27 Standard Oil Co Urea adducts of quaternary ammonium compounds
US2702774A (en) * 1950-06-16 1955-02-22 California Research Corp Process of preparation of free flowing composition containing quaternary ammonium compound
US2719129A (en) * 1951-06-30 1955-09-27 Colgate Palmolive Co Pressurized liquid room and air deodorant compositions
US2740744A (en) * 1956-04-03 Method of protecting seeds using-short
US2786797A (en) * 1954-05-18 1957-03-26 Hollingshead Corp Corrosion-inhibited quaternary ammonium compositions
US2826612A (en) * 1955-01-14 1958-03-11 Stamicarbon Preparation of urea crystals
US2830039A (en) * 1953-08-31 1958-04-08 Standard Oil Co Urea adducts of quaternary heterocyclic-nitrogen halides
US2865805A (en) * 1954-05-04 1958-12-23 Gallowhur Chemical Corp Quaternary ammonium naphthalene and naphthol sulfonates
US2875154A (en) * 1952-08-01 1959-02-24 California Research Corp Non-caking solid particulate detergents
US2932364A (en) * 1957-08-15 1960-04-12 Frederick C Binter Method for treatment of exhaust gases from internal combustion engines
US2970048A (en) * 1956-07-11 1961-01-31 Monsanto Chemicals Defoliating composition and method
US3016327A (en) * 1955-12-12 1962-01-09 Anderson Biocidal composition and method
US3044962A (en) * 1957-10-31 1962-07-17 British Nylon Spinners Ltd Preparation of detergent compositions
US3198251A (en) * 1960-08-26 1965-08-03 Hart Lab Inc Deodorant preparation
US3198746A (en) * 1962-06-11 1965-08-03 Monsanto Co Quaternary ammonium arylsulfonate solutions
US3278370A (en) * 1962-07-16 1966-10-11 Dow Chemical Co Surface active bacteriostatic agents
US3402242A (en) * 1964-07-20 1968-09-17 Parachlor Chemical Corp Non-irritant quaternary ammonium compound composition
US4202882A (en) * 1973-12-03 1980-05-13 Herbert Schwartz Novel deodorizing method
US4252785A (en) * 1979-07-09 1981-02-24 Hexcel Corporation Controlled release composition
US4370314A (en) * 1975-12-08 1983-01-25 Colgate-Palmolive Company Oral composition containing antibacterial agent
US4824867A (en) * 1986-08-08 1989-04-25 Smith Kim R Quaternary ammonium compounds
US4883917A (en) * 1985-10-01 1989-11-28 Ethyl Corporation Quaternary ammonium compounds
US5047577A (en) * 1985-10-01 1991-09-10 Ethyl Corporation Quaternary ammonium compounds

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US1785327A (en) * 1930-04-11 1930-12-16 Ostro Res Lab Inc Alkyl-phenyl ether
US2060850A (en) * 1932-11-08 1936-11-17 Du Pont Quaternary ammonium compounds and process for the production thereof
GB505429A (en) * 1937-07-29 1939-05-01 Deutsche Hydrierwerke Ag Improvements in or relating to the manufacture and use of disinfecting and like agents
US2176896A (en) * 1938-08-04 1939-10-24 Albert K Epstein Quaternary ammonium derivatives of amides
US2191678A (en) * 1938-04-02 1940-02-27 Squibb & Sons Inc Process of preparing tablets
US2200603A (en) * 1937-07-06 1940-05-14 Patchem A G Zur Beteiligung An Method for the improving of goods
US2281786A (en) * 1939-11-16 1942-05-05 Stauffer Chemical Co Insecticidal material
US2295504A (en) * 1938-08-01 1942-09-08 Wm S Merrell Co Cetyl quaternary ammonium compound
US2479850A (en) * 1949-08-23 Process of killing bacteria in pres

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US2479850A (en) * 1949-08-23 Process of killing bacteria in pres
US1785327A (en) * 1930-04-11 1930-12-16 Ostro Res Lab Inc Alkyl-phenyl ether
US2060850A (en) * 1932-11-08 1936-11-17 Du Pont Quaternary ammonium compounds and process for the production thereof
US2200603A (en) * 1937-07-06 1940-05-14 Patchem A G Zur Beteiligung An Method for the improving of goods
GB505429A (en) * 1937-07-29 1939-05-01 Deutsche Hydrierwerke Ag Improvements in or relating to the manufacture and use of disinfecting and like agents
US2191678A (en) * 1938-04-02 1940-02-27 Squibb & Sons Inc Process of preparing tablets
US2295504A (en) * 1938-08-01 1942-09-08 Wm S Merrell Co Cetyl quaternary ammonium compound
US2176896A (en) * 1938-08-04 1939-10-24 Albert K Epstein Quaternary ammonium derivatives of amides
US2281786A (en) * 1939-11-16 1942-05-05 Stauffer Chemical Co Insecticidal material

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2740744A (en) * 1956-04-03 Method of protecting seeds using-short
US2702774A (en) * 1950-06-16 1955-02-22 California Research Corp Process of preparation of free flowing composition containing quaternary ammonium compound
US2676955A (en) * 1950-10-21 1954-04-27 Standard Oil Co Urea adducts of quaternary ammonium compounds
US2719129A (en) * 1951-06-30 1955-09-27 Colgate Palmolive Co Pressurized liquid room and air deodorant compositions
US2875154A (en) * 1952-08-01 1959-02-24 California Research Corp Non-caking solid particulate detergents
US2830039A (en) * 1953-08-31 1958-04-08 Standard Oil Co Urea adducts of quaternary heterocyclic-nitrogen halides
US2865805A (en) * 1954-05-04 1958-12-23 Gallowhur Chemical Corp Quaternary ammonium naphthalene and naphthol sulfonates
US2786797A (en) * 1954-05-18 1957-03-26 Hollingshead Corp Corrosion-inhibited quaternary ammonium compositions
US2826612A (en) * 1955-01-14 1958-03-11 Stamicarbon Preparation of urea crystals
US3016327A (en) * 1955-12-12 1962-01-09 Anderson Biocidal composition and method
US2970048A (en) * 1956-07-11 1961-01-31 Monsanto Chemicals Defoliating composition and method
US2932364A (en) * 1957-08-15 1960-04-12 Frederick C Binter Method for treatment of exhaust gases from internal combustion engines
US3044962A (en) * 1957-10-31 1962-07-17 British Nylon Spinners Ltd Preparation of detergent compositions
US3198251A (en) * 1960-08-26 1965-08-03 Hart Lab Inc Deodorant preparation
US3198746A (en) * 1962-06-11 1965-08-03 Monsanto Co Quaternary ammonium arylsulfonate solutions
US3278370A (en) * 1962-07-16 1966-10-11 Dow Chemical Co Surface active bacteriostatic agents
US3402242A (en) * 1964-07-20 1968-09-17 Parachlor Chemical Corp Non-irritant quaternary ammonium compound composition
US4202882A (en) * 1973-12-03 1980-05-13 Herbert Schwartz Novel deodorizing method
US4370314A (en) * 1975-12-08 1983-01-25 Colgate-Palmolive Company Oral composition containing antibacterial agent
US4252785A (en) * 1979-07-09 1981-02-24 Hexcel Corporation Controlled release composition
US4883917A (en) * 1985-10-01 1989-11-28 Ethyl Corporation Quaternary ammonium compounds
US5047577A (en) * 1985-10-01 1991-09-10 Ethyl Corporation Quaternary ammonium compounds
US4824867A (en) * 1986-08-08 1989-04-25 Smith Kim R Quaternary ammonium compounds

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